# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 2120768'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 4o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_3                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Although the intensities appear to be strong, the available data
extend to 1.10 angstrom only. It could be that the data were never measured,
or that the resolution cut-off was applied during processing. The structure is
clearly of limited precision, but remains of value in the context of the set
of structures with which it is published. The coordinates also provide a 
suitable starting set for optimisation by DFT-D methods.
;
_vrf_PLAT089_3                   
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.15 Note
RESPONSE: This is related to the limited extent of the data 
and the fact that there are two independent sulfathiazole molecules in the 
asymmetric unit. This could have been mitigated to some extent by using
isotropic ADPs. However, the refinement with anisotropic ADPs behaves well
and leads to quite a significant improvement in the R-factors. Hence,
anisotropic ADPs were applied (with restraints for the diethylmalonate
molecule). The structure is clearly of limited precision, but remains of
value in the context of the set of structures with which it is published,
and provides a suitable starting model for optimisation by DFT-D methods.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, diethylmalonate (2:1) solvate'
_chemical_name_common            'Sulfathiazole, diethylmalonate solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C7 H12 O4'
_chemical_formula_sum            'C25 H30 N6 O8 S4'
_chemical_formula_weight         670.79
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   8.409(2)
_cell_length_b                   16.640(1)
_cell_length_c                   11.274(1)
_cell_angle_alpha                90
_cell_angle_beta                 101.37(2)
_cell_angle_gamma                90
_cell_volume                     1546.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      44.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.313
_shelx_estimated_absorpt_T_min   0.436
_shelx_estimated_absorpt_T_max   0.557
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            1335
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.655
_diffrn_reflns_theta_max         44.388
_diffrn_reflns_theta_full        44.388
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.548
_diffrn_reflns_point_group_measured_fraction_full 0.548
_reflns_number_total             1335
_reflns_number_gt                1302
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.092
_reflns_Friedel_fraction_max     0.092
_reflns_Friedel_fraction_full    0.092

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  4o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 4.60      21     22     95.5     1.23     701.7  135.85  0.0160  0.0051
4.60 - 3.06      44     44    100.0     1.18     566.9   84.76  0.0159  0.0072
3.06 - 2.45      63     63    100.0     1.14     352.9   60.45  0.0211  0.0117
2.45 - 2.10      64     64    100.0     1.12     176.2   42.73  0.0216  0.0178
2.10 - 1.91      64     64    100.0     1.09     175.7   39.29  0.0150  0.0183
1.91 - 1.77      67     67    100.0     1.10     159.8   41.08  0.0320  0.0203
1.77 - 1.66      58     58    100.0     1.09      96.9   32.85  0.0346  0.0251
1.66 - 1.57      75     75    100.0     1.09      88.0   30.39  0.0456  0.0258
1.57 - 1.51      55     55    100.0     1.11      81.0   30.95  0.0334  0.0270
1.51 - 1.44      67     67    100.0     1.06      67.1   26.45  0.0640  0.0285
1.44 - 1.39      59     60     98.3     1.05      50.6   23.86  0.0532  0.0328
1.39 - 1.35      71     72     98.6     1.07      61.9   25.64  0.0147  0.0304
1.35 - 1.31      60     60    100.0     1.10      48.1   25.53  0.0355  0.0324
1.31 - 1.27      69     69    100.0     1.06      52.0   23.88  0.0463  0.0335
1.27 - 1.24      61     63     96.8     1.02      57.4   25.16  0.0506  0.0324
1.24 - 1.21      67     67    100.0     1.07      39.0   20.64  0.0380  0.0377
1.21 - 1.18      70     71     98.6     1.06      50.7   22.06  0.0219  0.0333
1.18 - 1.16      59     59    100.0     1.08      55.8   23.83  0.0418  0.0344
1.16 - 1.14      63     63    100.0     1.05      33.6   19.02  0.0274  0.0424
1.14 - 1.12      55     55    100.0     1.04      30.3   17.16  0.0710  0.0458
1.12 - 1.10      67     68     98.5     1.07      33.3   18.20  0.0587  0.0431
#------------------------------------------------------------------------------
1.20 - 1.10     290    292     99.3     1.06      40.4   20.04  0.0399  0.0388
 Inf - 1.10    1279   1286     99.5     1.08     116.6   32.59  0.0213  0.0191
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0979P)²+1.0441P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_abs_structure_details 
;
Insufficient number of Friedel pairs to state result with any confidence.
Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_number_reflns         1335
_refine_ls_number_parameters     388
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.3084(3) 0.42303(15) 0.3974(2) 0.0453(8) Uani 1 1 d . . . . .
S12 S 0.3564(4) 0.27188(19) 0.2171(3) 0.0724(10) Uani 1 1 d . . . . .
O11 O 0.1956(8) 0.4652(4) 0.4563(8) 0.067(2) Uani 1 1 d . . . . .
O12 O 0.2838(9) 0.4287(4) 0.2669(6) 0.058(2) Uani 1 1 d . . . . .
N11 N 0.9669(13) 0.5407(7) 0.5958(10) 0.085(3) Uani 1 1 d . . . . .
H10 H 1.048550 0.524920 0.563238 0.127 Uiso 1 1 d R U . . .
H11 H 0.983741 0.574620 0.656908 0.127 Uiso 1 1 d R U . . .
N12 N 0.3046(11) 0.3311(5) 0.4380(7) 0.048(2) Uani 1 1 d . . . . .
N13 N 0.3100(12) 0.1946(6) 0.4004(8) 0.058(2) Uani 1 1 d . . . . .
H17 H 0.292857 0.181921 0.472643 0.087 Uiso 1 1 calc R U . . .
C11 C 0.8153(13) 0.5127(6) 0.5520(9) 0.049(3) Uani 1 1 d . . . . .
C12 C 0.6832(15) 0.5386(7) 0.5987(10) 0.059(3) Uani 1 1 d . . . . .
H12 H 0.699687 0.576207 0.663383 0.070 Uiso 1 1 calc R U . . .
C13 C 0.5302(12) 0.5112(6) 0.5540(9) 0.053(3) Uani 1 1 d . . . . .
H13 H 0.442044 0.528962 0.588507 0.064 Uiso 1 1 calc R U . . .
C14 C 0.5036(12) 0.4579(6) 0.4587(9) 0.044(3) Uani 1 1 d . . . . .
C15 C 0.6319(15) 0.4316(7) 0.4112(9) 0.054(3) Uani 1 1 d . . . . .
H15 H 0.614965 0.393841 0.346691 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7853(13) 0.4597(7) 0.4568(11) 0.060(3) Uani 1 1 d . . . . .
H16 H 0.872981 0.442087 0.421570 0.072 Uiso 1 1 calc R U . . .
C17 C 0.3201(12) 0.2713(8) 0.3656(9) 0.047(3) Uani 1 1 d . . . . .
C18 C 0.3279(17) 0.1368(8) 0.3162(14) 0.077(4) Uani 1 1 d . . . . .
H18 H 0.323756 0.080542 0.329925 0.093 Uiso 1 1 calc R U . . .
C19 C 0.351(2) 0.1677(9) 0.2187(14) 0.089(4) Uani 1 1 d . . . . .
H19 H 0.363521 0.136136 0.151039 0.107 Uiso 1 1 calc R U . . .
S21 S 0.2898(3) 0.08167(15) 0.6933(3) 0.0478(8) Uani 1 1 d . . . . .
S22 S 0.1779(4) 0.22906(17) 0.8556(3) 0.0715(10) Uani 1 1 d . . . . .
O21 O 0.2832(9) 0.0351(4) 0.5847(7) 0.067(2) Uani 1 1 d . . . . .
O22 O 0.1781(9) 0.0622(4) 0.7717(7) 0.064(2) Uani 1 1 d . . . . .
N21 N 0.9619(13) 0.0530(7) 0.9718(12) 0.101(4) Uani 1 1 d . . . . .
H20 H 0.980470 0.046692 1.050848 0.152 Uiso 1 1 d R U . . .
H21 H 1.043560 0.055352 0.933688 0.152 Uiso 1 1 d R U . . .
N22 N 0.2686(10) 0.1737(5) 0.6475(7) 0.043(2) Uani 1 1 d . . . . .
N23 N 0.2253(10) 0.3072(6) 0.6749(8) 0.050(2) Uani 1 1 d . . . . .
H27 H 0.245114 0.320472 0.603698 0.075 Uiso 1 1 calc R U . . .
C21 C 0.8036(15) 0.0593(7) 0.9072(13) 0.061(3) Uani 1 1 d . . . . .
C22 C 0.7731(16) 0.0691(7) 0.7840(13) 0.067(3) Uani 1 1 d . . . . .
H22 H 0.860729 0.072884 0.742504 0.080 Uiso 1 1 calc R U . . .
C23 C 0.6149(15) 0.0736(6) 0.7200(11) 0.060(3) Uani 1 1 d . . . . .
H23 H 0.594279 0.076282 0.634179 0.072 Uiso 1 1 calc R U . . .
C24 C 0.4871(12) 0.0742(5) 0.7800(10) 0.045(3) Uani 1 1 d . . . . .
C25 C 0.5146(15) 0.0675(6) 0.9042(10) 0.053(3) Uani 1 1 d . . . . .
H25 H 0.426661 0.068260 0.945665 0.064 Uiso 1 1 calc R U . . .
C26 C 0.6735(19) 0.0597(7) 0.9680(11) 0.070(4) Uani 1 1 d . . . . .
H26 H 0.693759 0.054626 1.053579 0.084 Uiso 1 1 calc R U . . .
C27 C 0.2285(12) 0.2309(6) 0.7157(9) 0.039(3) Uani 1 1 d . . . . .
C28 C 0.1876(15) 0.3622(8) 0.7563(15) 0.074(4) Uani 1 1 d . . . . .
H28 H 0.183630 0.418359 0.740601 0.088 Uiso 1 1 calc R U . . .
C29 C 0.1575(18) 0.3317(7) 0.8572(13) 0.073(4) Uani 1 1 d . . . . .
H29 H 0.128886 0.361923 0.921345 0.087 Uiso 1 1 calc R U . . .
O31 O 0.7792(9) 0.7148(5) 0.4168(7) 0.079(2) Uani 1 1 d D U . . .
O32 O 0.6193(12) 0.7452(6) 0.5481(9) 0.099(3) Uani 1 1 d D U . . .
O33 O 0.879(3) 0.8234(10) 0.7757(16) 0.195(6) Uani 1 1 d D U . . .
O34 O 0.896(2) 0.6901(9) 0.7846(12) 0.175(5) Uani 1 1 d D U . . .
C30 C 0.686(2) 0.6842(14) 0.2079(14) 0.148(7) Uani 1 1 d D U . . .
H30A H 0.591905 0.671919 0.144394 0.222 Uiso 1 1 calc R U . . .
H30B H 0.738825 0.733230 0.186463 0.222 Uiso 1 1 calc R U . . .
H30C H 0.763320 0.639440 0.215861 0.222 Uiso 1 1 calc R U . . .
C31 C 0.6330(15) 0.6965(11) 0.3244(11) 0.106(5) Uani 1 1 d D U . . .
H31A H 0.554896 0.741601 0.317461 0.127 Uiso 1 1 calc R U . . .
H31B H 0.579495 0.647415 0.346982 0.127 Uiso 1 1 calc R U . . .
C32 C 0.7501(13) 0.7378(8) 0.5206(9) 0.071(3) Uani 1 1 d D U . . .
C33 C 0.9085(13) 0.7575(8) 0.6017(9) 0.079(4) Uani 1 1 d D U . . .
H33A H 0.942676 0.812242 0.583022 0.095 Uiso 1 1 calc R U . . .
H33B H 0.992376 0.719179 0.586715 0.095 Uiso 1 1 calc R U . . .
C34 C 0.895(3) 0.7533(10) 0.7319(14) 0.143(7) Uani 1 1 d D U . . .
C35 C 0.917(3) 0.820(2) 0.9144(18) 0.253(15) Uani 1 1 d D U . . .
H35A H 0.969126 0.768950 0.946413 0.304 Uiso 1 1 calc R U . . .
H35B H 0.981587 0.866452 0.951796 0.304 Uiso 1 1 calc R U . . .
C36 C 0.745(3) 0.8248(16) 0.923(2) 0.190(10) Uani 1 1 d D U . . .
H36A H 0.736462 0.823609 1.008814 0.284 Uiso 1 1 calc R U . . .
H36B H 0.698698 0.874945 0.886445 0.284 Uiso 1 1 calc R U . . .
H36C H 0.686435 0.778993 0.881147 0.284 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.443(8) . ?
S11 O12 1.448(7) . ?
S11 N12 1.599(9) . ?
S11 C14 1.749(10) . ?
S12 C19 1.735(15) . ?
S12 C17 1.759(11) . ?
N11 C11 1.356(14) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.310(13) . ?
N13 C17 1.343(14) . ?
N13 C18 1.381(16) . ?
N13 H17 0.8800 . ?
C11 C16 1.373(14) . ?
C11 C12 1.389(14) . ?
C12 C13 1.364(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(14) . ?
C15 C16 1.374(15) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.261(18) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S21 O21 1.440(8) . ?
S21 O22 1.448(8) . ?
S21 N22 1.614(8) . ?
S21 C24 1.756(11) . ?
S22 C27 1.712(11) . ?
S22 C29 1.717(13) . ?
N21 C21 1.389(16) . ?
N21 H20 0.8800 . ?
N21 H21 0.8800 . ?
N22 C27 1.310(12) . ?
N23 C27 1.349(13) . ?
N23 C28 1.375(16) . ?
N23 H27 0.8800 . ?
C21 C22 1.372(17) . ?
C21 C26 1.401(17) . ?
C22 C23 1.385(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(15) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(14) . ?
C25 C26 1.392(17) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C28 C29 1.315(18) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
O31 C32 1.299(10) . ?
O31 C31 1.478(10) . ?
O32 C32 1.206(9) . ?
O33 C34 1.283(11) . ?
O33 C35 1.534(12) . ?
O34 C34 1.206(11) . ?
C30 C31 1.483(11) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.496(10) . ?
C33 C34 1.497(11) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C35 C36 1.470(12) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.4(5) . . ?
O11 S11 N12 106.4(4) . . ?
O12 S11 N12 110.3(4) . . ?
O11 S11 C14 108.0(5) . . ?
O12 S11 C14 108.3(5) . . ?
N12 S11 C14 105.9(5) . . ?
C19 S12 C17 88.5(7) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 122.6(7) . . ?
C17 N13 C18 116.0(10) . . ?
C17 N13 H17 122.0 . . ?
C18 N13 H17 122.0 . . ?
N11 C11 C16 121.3(10) . . ?
N11 C11 C12 121.4(10) . . ?
C16 C11 C12 117.3(9) . . ?
C13 C12 C11 121.5(9) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 120.0(9) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.5(9) . . ?
C15 C14 S11 119.4(8) . . ?
C13 C14 S11 121.1(8) . . ?
C14 C15 C16 120.0(10) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 121.7(10) . . ?
C11 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
N12 C17 N13 121.3(9) . . ?
N12 C17 S12 130.2(9) . . ?
N13 C17 S12 108.5(9) . . ?
C19 C18 N13 111.8(12) . . ?
C19 C18 H18 124.1 . . ?
N13 C18 H18 124.1 . . ?
C18 C19 S12 115.2(10) . . ?
C18 C19 H19 122.4 . . ?
S12 C19 H19 122.4 . . ?
O21 S21 O22 118.5(5) . . ?
O21 S21 N22 104.8(4) . . ?
O22 S21 N22 111.3(5) . . ?
O21 S21 C24 108.0(5) . . ?
O22 S21 C24 107.4(5) . . ?
N22 S21 C24 106.2(4) . . ?
C27 S22 C29 92.0(6) . . ?
C21 N21 H20 120.0 . . ?
C21 N21 H21 120.0 . . ?
H20 N21 H21 120.0 . . ?
C27 N22 S21 121.8(7) . . ?
C27 N23 C28 113.0(10) . . ?
C27 N23 H27 123.5 . . ?
C28 N23 H27 123.5 . . ?
C22 C21 N21 120.5(13) . . ?
C22 C21 C26 119.1(10) . . ?
N21 C21 C26 120.3(13) . . ?
C21 C22 C23 120.2(11) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.4(10) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 120.5(10) . . ?
C25 C24 S21 121.5(9) . . ?
C23 C24 S21 118.0(8) . . ?
C24 C25 C26 119.0(10) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C21 120.7(10) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
N22 C27 N23 118.4(9) . . ?
N22 C27 S22 131.8(8) . . ?
N23 C27 S22 109.8(8) . . ?
C29 C28 N23 115.4(11) . . ?
C29 C28 H28 122.3 . . ?
N23 C28 H28 122.3 . . ?
C28 C29 S22 109.8(10) . . ?
C28 C29 H29 125.1 . . ?
S22 C29 H29 125.1 . . ?
C32 O31 C31 114.7(9) . . ?
C34 O33 C35 110(2) . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O31 C31 C30 107.4(11) . . ?
O31 C31 H31A 110.2 . . ?
C30 C31 H31A 110.2 . . ?
O31 C31 H31B 110.2 . . ?
C30 C31 H31B 110.2 . . ?
H31A C31 H31B 108.5 . . ?
O32 C32 O31 127.2(10) . . ?
O32 C32 C33 124.6(10) . . ?
O31 C32 C33 108.1(9) . . ?
C32 C33 C34 110.9(12) . . ?
C32 C33 H33A 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
O34 C34 O33 126.5(17) . . ?
O34 C34 C33 121.8(15) . . ?
O33 C34 C33 111.6(15) . . ?
C36 C35 O33 93.4(19) . . ?
C36 C35 H35A 113.0 . . ?
O33 C35 H35A 113.0 . . ?
C36 C35 H35B 113.0 . . ?
O33 C35 H35B 113.0 . . ?
H35A C35 H35B 110.4 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 144.7(8) . . . . ?
O12 S11 N12 C17 16.3(9) . . . . ?
C14 S11 N12 C17 -100.6(9) . . . . ?
N11 C11 C12 C13 179.3(11) . . . . ?
C16 C11 C12 C13 1.4(16) . . . . ?
C11 C12 C13 C14 -1.3(16) . . . . ?
C12 C13 C14 C15 1.2(15) . . . . ?
C12 C13 C14 S11 -178.8(8) . . . . ?
O11 S11 C14 C15 -175.0(8) . . . . ?
O12 S11 C14 C15 -46.9(9) . . . . ?
N12 S11 C14 C15 71.4(9) . . . . ?
O11 S11 C14 C13 5.1(9) . . . . ?
O12 S11 C14 C13 133.2(8) . . . . ?
N12 S11 C14 C13 -108.5(9) . . . . ?
C13 C14 C15 C16 -1.4(15) . . . . ?
S11 C14 C15 C16 178.6(8) . . . . ?
N11 C11 C16 C15 -179.5(10) . . . . ?
C12 C11 C16 C15 -1.6(16) . . . . ?
C14 C15 C16 C11 1.7(16) . . . . ?
S11 N12 C17 N13 -177.3(7) . . . . ?
S11 N12 C17 S12 3.2(14) . . . . ?
C18 N13 C17 N12 179.9(10) . . . . ?
C18 N13 C17 S12 -0.5(12) . . . . ?
C19 S12 C17 N12 -179.6(11) . . . . ?
C19 S12 C17 N13 0.8(9) . . . . ?
C17 N13 C18 C19 -0.3(17) . . . . ?
N13 C18 C19 S12 1.0(18) . . . . ?
C17 S12 C19 C18 -1.1(13) . . . . ?
O21 S21 N22 C27 162.8(7) . . . . ?
O22 S21 N22 C27 33.5(9) . . . . ?
C24 S21 N22 C27 -83.1(9) . . . . ?
N21 C21 C22 C23 178.6(11) . . . . ?
C26 C21 C22 C23 -4.6(17) . . . . ?
C21 C22 C23 C24 4.8(16) . . . . ?
C22 C23 C24 C25 -2.2(15) . . . . ?
C22 C23 C24 S21 178.9(8) . . . . ?
O21 S21 C24 C25 -140.9(8) . . . . ?
O22 S21 C24 C25 -12.1(9) . . . . ?
N22 S21 C24 C25 107.1(8) . . . . ?
O21 S21 C24 C23 37.9(9) . . . . ?
O22 S21 C24 C23 166.8(8) . . . . ?
N22 S21 C24 C23 -74.0(9) . . . . ?
C23 C24 C25 C26 -0.4(15) . . . . ?
S21 C24 C25 C26 178.4(8) . . . . ?
C24 C25 C26 C21 0.5(17) . . . . ?
C22 C21 C26 C25 2.0(18) . . . . ?
N21 C21 C26 C25 178.8(11) . . . . ?
S21 N22 C27 N23 175.0(6) . . . . ?
S21 N22 C27 S22 -4.3(13) . . . . ?
C28 N23 C27 N22 -177.7(9) . . . . ?
C28 N23 C27 S22 1.8(10) . . . . ?
C29 S22 C27 N22 178.2(11) . . . . ?
C29 S22 C27 N23 -1.2(8) . . . . ?
C27 N23 C28 C29 -1.6(15) . . . . ?
N23 C28 C29 S22 0.7(15) . . . . ?
C27 S22 C29 C28 0.3(11) . . . . ?
C32 O31 C31 C30 171.2(14) . . . . ?
C31 O31 C32 O32 0.1(19) . . . . ?
C31 O31 C32 C33 -177.4(11) . . . . ?
O32 C32 C33 C34 24.3(18) . . . . ?
O31 C32 C33 C34 -158.1(12) . . . . ?
C35 O33 C34 O34 18(4) . . . . ?
C35 O33 C34 C33 -162.8(18) . . . . ?
C32 C33 C34 O34 79(2) . . . . ?
C32 C33 C34 O33 -100.5(19) . . . . ?
C34 O33 C35 C36 -104(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.88 2.13 2.990(14) 163.9 1_655 yes
N11 H11 O12 0.88 2.58 3.009(12) 110.6 2_665 yes
N11 H11 O34 0.88 2.59 3.40(2) 152.9 . yes
N13 H17 N22 0.88 2.03 2.896(13) 169.3 . yes
N21 H21 O22 0.88 2.33 3.168(16) 158.5 1_655 yes
N23 H27 N12 0.88 2.04 2.906(12) 170.1 . yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 2120771'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 7o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_6                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.10 angstrom. Data were integrated to 0.84
angstrom resolution, but truncated at 0.95 angstrom resolution for this
refinement.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, oxalic acid diethyl ester (2:1) solvate'
_chemical_name_common            'Sulfathiazole, diethyloxalate solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C6 H10 O4'
_chemical_formula_sum            'C24 H28 N6 O8 S4'
_chemical_formula_weight         656.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.416(2)
_cell_length_b                   17.394(3)
_cell_length_c                   10.342(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.70(3)
_cell_angle_gamma                90
_cell_volume                     1464.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4521
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      21.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.382
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4521
_diffrn_reflns_av_unetI/netI     0.1871
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.342
_diffrn_reflns_theta_max         21.961
_diffrn_reflns_theta_full        21.961
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             1686
_reflns_number_gt                772
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  7o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.75      34     36     94.4     3.67     646.2   43.96  0.0799  0.0154
3.75 - 2.50      74     75     98.7     3.25     293.7   18.56  0.0758  0.0349
2.50 - 1.98     111    112     99.1     3.03     130.9    9.83  0.0891  0.0688
1.98 - 1.71     105    107     98.1     3.02      95.2    8.01  0.0559  0.1019
1.71 - 1.56     106    107     99.1     2.93      55.3    5.19  0.0603  0.1623
1.56 - 1.44     107    108     99.1     3.04      56.0    4.90  0.0714  0.1611
1.44 - 1.36     104    105     99.0     2.91      39.3    3.76  0.0924  0.2206
1.36 - 1.28     118    125     94.4     2.71      31.6    3.00  0.1061  0.2925
1.28 - 1.23      97     97    100.0     2.78      32.3    2.85  0.0979  0.3160
1.23 - 1.18     106    114     93.0     2.64      34.6    3.01  0.0991  0.3059
1.18 - 1.13     130    141     92.2     2.42      25.4    2.26  0.1171  0.4246
1.13 - 1.10      88     96     91.7     2.25      20.6    1.74  0.1301  0.5522
1.10 - 1.06     110    127     86.6     1.91      22.4    1.64  0.1473  0.5596
1.06 - 1.03     113    124     91.1     1.81      16.8    1.23  0.1539  0.7821
1.03 - 1.00     120    138     87.0     1.75      13.8    1.10  0.1879  0.9122
1.00 - 0.98      84    104     80.8     1.68       9.5    0.89  0.2056  1.2233
0.98 - 0.95     127    148     85.8     1.75       9.5    0.78  0.2660  1.2720
0.95 - 0.93     105    119     88.2     1.74      10.5    0.81  0.2374  1.1568
0.93 - 0.91     121    146     82.9     1.57       8.7    0.74  0.2510  1.3716
0.91 - 0.89      82    150     54.7     0.93       6.1    0.52  0.3223  1.9814
0.89 - 0.85      98    321     30.5     0.46       5.7    0.46  0.3555  2.1928
0.85 - 0.84       5     75      6.7     0.09       7.5    0.64  0.1100  1.8630
#--------------------------------------------------------------------------------
0.94 - 0.84     355    749     47.4     0.81       7.6    0.61  0.2674  1.6155
 Inf - 0.84    2145   2675     80.2     1.99      51.8    3.99  0.0884  0.2108
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The H atoms of the NH2 group could not readily be refined, so they were
placed in-plane and allowed to ride. This is an approximation.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1686
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1296
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_restrained_S_all      0.791
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.069

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S -0.0204(3) 0.33758(13) 0.1413(2) 0.0585(7) Uani 1 1 d . . . . .
S12 S -0.1296(3) 0.47038(14) 0.32396(18) 0.0704(8) Uani 1 1 d . . . . .
O11 O -0.0291(6) 0.2981(3) 0.0144(5) 0.088(2) Uani 1 1 d . . . . .
O12 O -0.1255(5) 0.3107(3) 0.2141(4) 0.0781(19) Uani 1 1 d . . . . .
N11 N 0.6661(8) 0.3042(4) 0.4537(7) 0.104(3) Uani 1 1 d . . . . .
H10 H 0.747442 0.315054 0.417539 0.156 Uiso 1 1 calc R U . . .
H11 H 0.686998 0.287613 0.536690 0.156 Uiso 1 1 calc R U . . .
N12 N -0.0411(7) 0.4238(4) 0.0949(5) 0.067(2) Uani 1 1 d . . . . .
N13 N -0.0437(7) 0.5487(4) 0.1531(5) 0.0398(19) Uani 1 1 d . . . . .
H17 H -0.013784 0.562178 0.080756 0.060 Uiso 1 1 calc R U . . .
C11 C 0.5078(10) 0.3131(4) 0.3812(9) 0.059(2) Uani 1 1 d . . . . .
C12 C 0.4673(11) 0.3385(5) 0.2524(9) 0.068(2) Uani 1 1 d . . . . .
H12 H 0.552437 0.351402 0.210945 0.081 Uiso 1 1 calc R U . . .
C13 C 0.3097(11) 0.3459(5) 0.1823(7) 0.062(2) Uani 1 1 d . . . . .
H13 H 0.286484 0.363196 0.092311 0.074 Uiso 1 1 calc R U . . .
C14 C 0.1802(8) 0.3289(4) 0.2382(7) 0.0391(18) Uani 1 1 d . . . . .
C15 C 0.2163(9) 0.3051(4) 0.3674(8) 0.049(2) Uani 1 1 d . . . . .
H15 H 0.130334 0.294344 0.409053 0.059 Uiso 1 1 calc R U . . .
C16 C 0.3811(11) 0.2966(4) 0.4395(7) 0.063(2) Uani 1 1 d . . . . .
H16 H 0.405641 0.279151 0.529417 0.075 Uiso 1 1 calc R U . . .
C17 C -0.0632(9) 0.4848(6) 0.1793(7) 0.059(3) Uani 1 1 d . . . . .
C18 C -0.0722(8) 0.6036(4) 0.2485(8) 0.058(2) Uani 1 1 d . . . . .
H18 H -0.059618 0.657697 0.242587 0.070 Uiso 1 1 calc R U . . .
C19 C -0.1200(9) 0.5669(5) 0.3488(7) 0.057(2) Uani 1 1 d . . . . .
H19 H -0.144709 0.591989 0.422969 0.069 Uiso 1 1 calc R U . . .
O30 O 0.4982(6) 0.5423(3) 0.3486(5) 0.0709(17) Uani 1 1 d . . . . .
O31 O 0.2894(7) 0.5037(3) 0.4307(5) 0.0705(18) Uani 1 1 d . . . . .
C31 C 0.4305(11) 0.5127(5) 0.4392(7) 0.057(2) Uani 1 1 d . . . . .
C32 C 0.3852(10) 0.5697(6) 0.2271(7) 0.099(4) Uani 1 1 d . . . . .
H32A H 0.302945 0.529189 0.191881 0.119 Uiso 1 1 calc R U . . .
H32B H 0.326002 0.615316 0.248117 0.119 Uiso 1 1 calc R U . . .
C33 C 0.4651(11) 0.5889(7) 0.1303(8) 0.142(5) Uani 1 1 d . . . . .
H33A H 0.549066 0.627836 0.165827 0.213 Uiso 1 1 calc R U . . .
H33B H 0.385537 0.609593 0.051840 0.213 Uiso 1 1 calc R U . . .
H33C H 0.517334 0.543045 0.104651 0.213 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.381(4) . ?
S11 O11 1.466(5) . ?
S11 N12 1.570(7) . ?
S11 C14 1.738(7) . ?
S12 C19 1.697(8) . ?
S12 C17 1.743(8) . ?
N11 C11 1.361(9) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.417(9) . ?
N13 C17 1.165(9) . ?
N13 C18 1.437(8) . ?
N13 H17 0.8800 . ?
C11 C12 1.363(9) . ?
C11 C16 1.381(9) . ?
C12 C13 1.347(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.358(8) . ?
C15 C16 1.406(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.363(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C31 1.319(8) . ?
O30 C32 1.450(8) . ?
O31 C31 1.178(8) . ?
C31 C31 1.549(15) 3_666 ?
C32 C33 1.381(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 115.8(3) . . ?
O12 S11 N12 116.9(3) . . ?
O11 S11 N12 101.4(3) . . ?
O12 S11 C14 108.6(3) . . ?
O11 S11 C14 107.2(3) . . ?
N12 S11 C14 106.0(3) . . ?
C19 S12 C17 88.5(4) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 123.3(6) . . ?
C17 N13 C18 114.6(7) . . ?
C17 N13 H17 122.7 . . ?
C18 N13 H17 122.7 . . ?
N11 C11 C12 122.8(8) . . ?
N11 C11 C16 119.5(8) . . ?
C12 C11 C16 117.7(8) . . ?
C13 C12 C11 121.6(7) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 121.7(7) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 118.1(7) . . ?
C15 C14 S11 122.4(6) . . ?
C13 C14 S11 119.5(6) . . ?
C14 C15 C16 119.9(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.9(7) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N13 C17 N12 121.5(8) . . ?
N13 C17 S12 115.6(6) . . ?
N12 C17 S12 122.8(8) . . ?
C19 C18 N13 110.1(7) . . ?
C19 C18 H18 125.0 . . ?
N13 C18 H18 125.0 . . ?
C18 C19 S12 111.1(5) . . ?
C18 C19 H19 124.4 . . ?
S12 C19 H19 124.4 . . ?
C31 O30 C32 115.9(5) . . ?
O31 C31 O30 127.4(7) . . ?
O31 C31 C31 124.2(9) . 3_666 ?
O30 C31 C31 108.3(9) . 3_666 ?
C33 C32 O30 112.0(7) . . ?
C33 C32 H32A 109.2 . . ?
O30 C32 H32A 109.2 . . ?
C33 C32 H32B 109.2 . . ?
O30 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 44.2(7) . . . . ?
O11 S11 N12 C17 171.2(6) . . . . ?
C14 S11 N12 C17 -77.0(7) . . . . ?
N11 C11 C12 C13 179.1(8) . . . . ?
C16 C11 C12 C13 -1.4(12) . . . . ?
C11 C12 C13 C14 0.8(13) . . . . ?
C12 C13 C14 C15 0.7(11) . . . . ?
C12 C13 C14 S11 -178.6(6) . . . . ?
O12 S11 C14 C15 -5.0(7) . . . . ?
O11 S11 C14 C15 -130.8(6) . . . . ?
N12 S11 C14 C15 121.5(6) . . . . ?
O12 S11 C14 C13 174.3(6) . . . . ?
O11 S11 C14 C13 48.4(7) . . . . ?
N12 S11 C14 C13 -59.2(6) . . . . ?
C13 C14 C15 C16 -1.6(10) . . . . ?
S11 C14 C15 C16 177.7(6) . . . . ?
N11 C11 C16 C15 180.0(7) . . . . ?
C12 C11 C16 C15 0.5(12) . . . . ?
C14 C15 C16 C11 1.0(11) . . . . ?
C18 N13 C17 N12 179.6(6) . . . . ?
C18 N13 C17 S12 2.3(10) . . . . ?
S11 N12 C17 N13 163.5(7) . . . . ?
S11 N12 C17 S12 -19.4(9) . . . . ?
C19 S12 C17 N13 -2.1(7) . . . . ?
C19 S12 C17 N12 -179.4(7) . . . . ?
C17 N13 C18 C19 -1.2(10) . . . . ?
N13 C18 C19 S12 -0.4(8) . . . . ?
C17 S12 C19 C18 1.3(6) . . . . ?
C32 O30 C31 O31 2.7(12) . . . . ?
C32 O30 C31 C31 -179.7(8) . . . 3_666 ?
C31 O30 C32 C33 -170.9(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.88 2.59 3.382(8) 149.8 1_655 yes
N13 H17 S11 0.88 2.95 3.783(6) 157.5 3_565 yes
N13 H17 N12 0.88 2.00 2.872(8) 170.8 3_565 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_16
_database_code_depnum_ccdc_archive 'CCDC 2120778'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 17o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_16                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.20 angstrom. Data were integrated to 0.84
angstrom resolution, but truncated at 1.00 angstrom resolution for refinement.
This still gives well below 50% observed at the 2sigma(I) level, so is probably
optimistic. The structure (especially the solvent molecule) is of limited
precision, remains of value in the context of the set of structures with which
it is published. The coordinates also provide a suitable starting set for
optimisation by DFT-D methods.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, cyclohexanone (1:1) solvate'
_chemical_name_common            'Sulfathiazole, cyclohexanone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C6 H10 O'
_chemical_formula_sum            'C15 H19 N3 O3 S2'
_chemical_formula_weight         353.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.487(3)
_cell_length_b                   12.332(4)
_cell_length_c                   22.259(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.19(3)
_cell_angle_gamma                90
_cell_volume                     1775.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5034
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      20.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.316
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_reflns_number            5034
_diffrn_reflns_av_unetI/netI     0.2336
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.835
_diffrn_reflns_theta_max         20.808
_diffrn_reflns_theta_full        20.808
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             1803
_reflns_number_gt                668
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  17o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.69      41     46     89.1     3.24     590.3   36.61  0.1068  0.0180
3.69 - 2.48      94     99     94.9     3.20     223.7   15.79  0.0829  0.0450
2.48 - 1.94     137    144     95.1     2.90      99.1    7.94  0.0792  0.1046
1.94 - 1.70     129    131     98.5     2.89      60.3    4.99  0.0766  0.1677
1.70 - 1.54     133    139     95.7     2.89      42.1    3.77  0.0792  0.2315
1.54 - 1.43     141    143     98.6     2.92      31.8    3.12  0.0992  0.3034
1.43 - 1.34     132    135     97.8     2.81      20.9    2.17  0.1486  0.4461
1.34 - 1.27     130    135     96.3     2.77      23.3    2.23  0.1389  0.4346
1.27 - 1.22     131    135     97.0     2.79      23.9    2.11  0.1339  0.4565
1.22 - 1.17     140    143     97.9     2.59      19.2    1.62  0.1711  0.6048
1.17 - 1.13     132    134     98.5     2.54      14.2    1.21  0.1945  0.8126
1.13 - 1.09     138    151     91.4     2.26      13.1    1.11  0.2281  0.9365
1.09 - 1.05     164    184     89.1     2.10       9.8    0.81  0.2757  1.2414
1.05 - 1.02     142    154     92.2     1.99       7.8    0.64  0.3124  1.6345
1.02 - 1.00      91    103     88.3     1.76       7.5    0.58  0.3104  1.8122
1.00 - 0.97     177    195     90.8     1.91       5.9    0.51  0.3595  2.1929
0.97 - 0.95     107    123     87.0     1.59       5.9    0.43  0.3928  2.3925
0.95 - 0.93     121    140     86.4     1.72       5.1    0.42  0.3279  2.5998
0.93 - 0.91     145    182     79.7     1.48       4.9    0.37  0.4162  2.8199
0.91 - 0.88     157    277     56.7     0.90       4.3    0.35  0.3768  3.0320
0.88 - 0.85      93    302     30.8     0.41       4.4    0.31  0.3651  3.2046
0.85 - 0.84       5     86      5.8     0.06       2.3    0.15  0.0000  6.8174
#------------------------------------------------------------------------------
0.94 - 0.84     465    918     50.7     0.85       4.6    0.36  0.3717  2.9258
 Inf - 0.84    2680   3281     81.7     2.01      37.1    2.86  0.1104  0.3165
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The cyclohexanone solvate molecule shows large displacement ellipsoids
and required restraints to maintain a reasonable geometry. Given the
limited data resolution, no attempt was made to model disorder or
anisotropic ADPs. The solvent position should be viewed as indicative.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1021P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1803
_refine_ls_number_parameters     169
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1671
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.2309
_refine_ls_wR_factor_gt          0.2083
_refine_ls_goodness_of_fit_ref   0.818
_refine_ls_restrained_S_all      0.837
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.077

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.3169(5) 0.4725(3) 0.13340(14) 0.0679(11) Uani 1 1 d . . . . .
S12 S 0.0249(5) 0.6446(3) 0.05409(15) 0.0829(13) Uani 1 1 d . . . . .
O11 O 0.4356(11) 0.3758(6) 0.1458(3) 0.083(3) Uani 1 1 d . . . . .
O12 O 0.0943(10) 0.4684(6) 0.1412(3) 0.079(2) Uani 1 1 d . . . . .
N11 N 0.6584(15) 0.8301(9) 0.2881(4) 0.114(4) Uani 1 1 d . . . . .
H10 H 0.790690 0.845957 0.288198 0.170 Uiso 1 1 calc R U . . .
H11 H 0.578431 0.866892 0.311033 0.170 Uiso 1 1 calc R U . . .
N12 N 0.3609(13) 0.5035(7) 0.0646(4) 0.063(3) Uani 1 1 d . . . . .
N13 N 0.2957(14) 0.6119(7) -0.0186(4) 0.063(3) Uani 1 1 d . . . . .
H17 H 0.403420 0.585930 -0.035711 0.095 Uiso 1 1 calc R U . . .
C11 C 0.575(2) 0.7459(10) 0.2512(5) 0.071(4) Uani 1 1 d . . . . .
C12 C 0.6997(18) 0.6878(12) 0.2151(6) 0.080(4) Uani 1 1 d . . . . .
H12 H 0.841173 0.707378 0.214360 0.096 Uiso 1 1 calc R U . . .
C13 C 0.6239(19) 0.6017(10) 0.1798(5) 0.073(4) Uani 1 1 d . . . . .
H13 H 0.714144 0.560681 0.156834 0.087 Uiso 1 1 calc R U . . .
C14 C 0.4196(18) 0.5765(9) 0.1783(4) 0.058(3) Uani 1 1 d . . . . .
C15 C 0.2924(17) 0.6361(11) 0.2148(5) 0.073(4) Uani 1 1 d . . . . .
H15 H 0.150452 0.617284 0.214993 0.087 Uiso 1 1 calc R U . . .
C16 C 0.366(2) 0.7188(11) 0.2493(5) 0.086(4) Uani 1 1 d . . . . .
H16 H 0.274840 0.758924 0.272474 0.103 Uiso 1 1 calc R U . . .
C17 C 0.2453(17) 0.5791(9) 0.0357(5) 0.060(3) Uani 1 1 d . . . . .
C18 C 0.168(2) 0.6884(11) -0.0458(6) 0.088(4) Uani 1 1 d . . . . .
H18 H 0.185923 0.717859 -0.084503 0.105 Uiso 1 1 calc R U . . .
C19 C 0.016(2) 0.7172(10) -0.0118(6) 0.092(4) Uani 1 1 d . . . . .
H19 H -0.084092 0.771085 -0.022681 0.110 Uiso 1 1 calc R U . . .
O30 O 0.603(2) 0.8129(14) 0.0440(7) 0.269(5) Uiso 1 1 d D U . . .
C30 C 0.570(2) 0.8797(14) 0.0801(9) 0.269(5) Uiso 1 1 d D U . . .
C31 C 0.741(2) 0.9354(14) 0.1116(8) 0.269(5) Uiso 1 1 d D U . . .
H31A H 0.863793 0.928946 0.087780 0.322 Uiso 1 1 calc R U . . .
H31B H 0.774473 0.899028 0.150754 0.322 Uiso 1 1 calc R U . . .
C32 C 0.702(3) 1.0498(12) 0.1224(9) 0.269(5) Uiso 1 1 d D U . . .
H32A H 0.718285 1.090675 0.084733 0.322 Uiso 1 1 calc R U . . .
H32B H 0.807291 1.077009 0.153194 0.322 Uiso 1 1 calc R U . . .
C33 C 0.497(3) 1.0716(12) 0.1425(8) 0.269(5) Uiso 1 1 d D U . . .
H33A H 0.474288 1.150980 0.142269 0.322 Uiso 1 1 calc R U . . .
H33B H 0.493328 1.046346 0.184651 0.322 Uiso 1 1 calc R U . . .
C34 C 0.328(2) 1.0200(14) 0.1059(9) 0.269(5) Uiso 1 1 d D U . . .
H34A H 0.312433 1.055697 0.066007 0.322 Uiso 1 1 calc R U . . .
H34B H 0.197468 1.030037 0.125646 0.322 Uiso 1 1 calc R U . . .
C35 C 0.365(2) 0.9029(14) 0.0976(9) 0.269(5) Uiso 1 1 d D U . . .
H35A H 0.343578 0.864490 0.135721 0.322 Uiso 1 1 calc R U . . .
H35B H 0.262425 0.874583 0.066333 0.322 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.435(7) . ?
S11 O12 1.467(7) . ?
S11 N12 1.625(8) . ?
S11 C14 1.729(11) . ?
S12 C19 1.715(12) . ?
S12 C17 1.717(11) . ?
N11 C11 1.408(13) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.332(12) . ?
N13 C17 1.339(11) . ?
N13 C18 1.366(14) . ?
N13 H17 0.8800 . ?
C11 C12 1.383(13) . ?
C11 C16 1.394(15) . ?
C12 C13 1.390(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.359(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.406(13) . ?
C15 C16 1.343(15) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.334(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C30 1.181(9) . ?
C30 C35 1.442(11) . ?
C30 C31 1.443(11) . ?
C31 C32 1.458(11) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.458(11) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.464(11) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.478(11) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.8(5) . . ?
O11 S11 N12 104.3(5) . . ?
O12 S11 N12 111.2(5) . . ?
O11 S11 C14 109.1(5) . . ?
O12 S11 C14 107.4(5) . . ?
N12 S11 C14 106.5(5) . . ?
C19 S12 C17 91.0(6) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 119.2(8) . . ?
C17 N13 C18 115.4(10) . . ?
C17 N13 H17 122.3 . . ?
C18 N13 H17 122.3 . . ?
C12 C11 C16 118.0(12) . . ?
C12 C11 N11 120.2(12) . . ?
C16 C11 N11 121.8(11) . . ?
C11 C12 C13 121.7(11) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 119.5(10) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 118.6(11) . . ?
C13 C14 S11 121.1(9) . . ?
C15 C14 S11 120.2(10) . . ?
C16 C15 C14 121.9(11) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C11 120.1(11) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N12 C17 N13 118.7(10) . . ?
N12 C17 S12 131.6(9) . . ?
N13 C17 S12 109.6(9) . . ?
C19 C18 N13 112.4(12) . . ?
C19 C18 H18 123.8 . . ?
N13 C18 H18 123.8 . . ?
C18 C19 S12 111.5(11) . . ?
C18 C19 H19 124.2 . . ?
S12 C19 H19 124.2 . . ?
O30 C30 C35 122.5(9) . . ?
O30 C30 C31 119.4(9) . . ?
C35 C30 C31 117.9(9) . . ?
C30 C31 C32 113.8(9) . . ?
C30 C31 H31A 108.8 . . ?
C32 C31 H31A 108.8 . . ?
C30 C31 H31B 108.8 . . ?
C32 C31 H31B 108.8 . . ?
H31A C31 H31B 107.7 . . ?
C31 C32 C33 113.8(9) . . ?
C31 C32 H32A 108.8 . . ?
C33 C32 H32A 108.8 . . ?
C31 C32 H32B 108.8 . . ?
C33 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C32 C33 C34 114.3(9) . . ?
C32 C33 H33A 108.7 . . ?
C34 C33 H33A 108.7 . . ?
C32 C33 H33B 108.7 . . ?
C34 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 C35 111.9(9) . . ?
C33 C34 H34A 109.2 . . ?
C35 C34 H34A 109.2 . . ?
C33 C34 H34B 109.2 . . ?
C35 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C30 C35 C34 112.8(9) . . ?
C30 C35 H35A 109.0 . . ?
C34 C35 H35A 109.0 . . ?
C30 C35 H35B 109.0 . . ?
C34 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 168.5(9) . . . . ?
O12 S11 N12 C17 40.5(10) . . . . ?
C14 S11 N12 C17 -76.2(10) . . . . ?
C16 C11 C12 C13 -2.9(18) . . . . ?
N11 C11 C12 C13 177.6(12) . . . . ?
C11 C12 C13 C14 3.1(18) . . . . ?
C12 C13 C14 C15 -2.6(17) . . . . ?
C12 C13 C14 S11 178.1(9) . . . . ?
O11 S11 C14 C13 52.5(11) . . . . ?
O12 S11 C14 C13 -178.7(9) . . . . ?
N12 S11 C14 C13 -59.5(11) . . . . ?
O11 S11 C14 C15 -126.7(8) . . . . ?
O12 S11 C14 C15 2.0(10) . . . . ?
N12 S11 C14 C15 121.2(9) . . . . ?
C13 C14 C15 C16 2.1(18) . . . . ?
S11 C14 C15 C16 -178.6(10) . . . . ?
C14 C15 C16 C11 -2(2) . . . . ?
C12 C11 C16 C15 2.3(19) . . . . ?
N11 C11 C16 C15 -178.2(12) . . . . ?
S11 N12 C17 N13 173.4(8) . . . . ?
S11 N12 C17 S12 -9.2(15) . . . . ?
C18 N13 C17 N12 179.1(10) . . . . ?
C18 N13 C17 S12 1.2(12) . . . . ?
C19 S12 C17 N12 -179.6(12) . . . . ?
C19 S12 C17 N13 -2.0(8) . . . . ?
C17 N13 C18 C19 0.7(16) . . . . ?
N13 C18 C19 S12 -2.3(15) . . . . ?
C17 S12 C19 C18 2.5(11) . . . . ?
O30 C30 C31 C32 142(2) . . . . ?
C35 C30 C31 C32 -42(3) . . . . ?
C30 C31 C32 C33 43(2) . . . . ?
C31 C32 C33 C34 -49(2) . . . . ?
C32 C33 C34 C35 51(2) . . . . ?
O30 C30 C35 C34 -140(2) . . . . ?
C31 C30 C35 C34 44(3) . . . . ?
C33 C34 C35 C30 -48(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H11 O12 0.88 2.03 2.907(11) 173.0 2 yes
N11 H10 O11 0.88 2.25 2.976(13) 139.5 2_655 yes
N13 H17 S11 0.88 3.02 3.856(9) 159.4 3_665 yes
N13 H17 N12 0.88 2.03 2.892(12) 167.4 3_665 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10
_database_code_depnum_ccdc_archive 'CCDC 2120772'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 11o
#===============================================================================
# start Validation Reply Form
_vrf_PLAT029_10                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.844 Why?  
RESPONSE: The data are uniformly >90% complete up to ca 0.93 angstrom. The 
resolution shell 0.93-0.84 angstrom is only ca 50% complete, which leads
to this relatively low fraction overall. The more serious issue with the data
is the R(int) value, which is uniformly ca 16%. This probably indicates some 
issue with the crystal.
;
_vrf_PLAT201_10                  
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         14 Report
RESPONSE: The data do not support anisotropic refinement. Only S atoms are
refined anisotropically, but these are restrained to resemble isotropic
behaviour (ISOR in SHELX).
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, tetramethylene sulfone (1:1) solvate'
_chemical_name_common            'Sulfathiazole, sulfalone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H8 O2 S'
_chemical_formula_sum            'C13 H17 N3 O4 S3'
_chemical_formula_weight         375.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.036(1)
_cell_length_b                   21.020(4)
_cell_length_c                   12.791(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.44(3)
_cell_angle_gamma                90
_cell_volume                     1618.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6447
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      25.08

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.481
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6447
_diffrn_reflns_av_unetI/netI     0.2137
_diffrn_reflns_av_R_equivalents  0.1754
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.868
_diffrn_reflns_theta_max         25.082
_diffrn_reflns_theta_full        25.082
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.844
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.844
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.844
_reflns_number_total             2422
_reflns_number_gt                1313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#===============================================================================
INTENSITY STATISTICS FOR DATASET # 1  11o.hkl
#===============================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#===============================================================================
 Inf - 3.72      38     41     92.7     3.24     734.4   38.97  0.1800  0.0198
3.72 - 2.45      86     89     96.6     2.97     375.2   19.40  0.1961  0.0407
2.45 - 1.92     128    130     98.5     3.05     241.5   13.32  0.2147  0.0624
1.92 - 1.68     124    126     98.4     3.04     164.9    9.11  0.1485  0.0883
1.68 - 1.51     128    130     98.5     3.03     138.4    7.34  0.2014  0.1095
1.51 - 1.41     121    124     97.6     2.91     154.1    7.67  0.1745  0.1155
1.41 - 1.33     130    130    100.0     3.02     101.6    5.83  0.1957  0.1546
1.33 - 1.26     122    126     96.8     2.96     101.0    5.48  0.1843  0.1691
1.26 - 1.20     122    127     96.1     2.92     115.0    5.57  0.1623  0.1620
1.20 - 1.15     139    143     97.2     2.71     132.9    4.89  0.1275  0.1700
1.15 - 1.11     132    137     96.4     2.55      83.8    3.65  0.1577  0.2542
1.11 - 1.08     102    109     93.6     2.54      81.3    3.87  0.1478  0.2510
1.08 - 1.04     154    158     97.5     2.42      73.5    3.08  0.1506  0.2999
1.04 - 1.02      88     93     94.6     2.37      60.0    2.63  0.1456  0.3560
1.02 - 0.99     142    152     93.4     2.32      60.9    2.61  0.1373  0.3531
0.99 - 0.97     107    114     93.9     2.06      51.1    2.13  0.1564  0.4669
0.97 - 0.95     130    139     93.5     2.10      40.3    1.76  0.1815  0.5689
0.95 - 0.93     127    132     96.2     2.14      41.4    1.80  0.1598  0.5412
0.93 - 0.91     122    132     92.4     1.95      45.7    1.84  0.1450  0.5032
0.91 - 0.88     146    253     57.7     1.09      43.2    1.55  0.1853  0.5623
0.88 - 0.84      98    385     25.5     0.38      42.7    1.43  0.1526  0.6046
#------------------------------------------------------------------------------
0.94 - 0.84     432    838     51.6     0.98      43.2    1.63  0.1599  0.5568
 Inf - 0.84    2486   2970     83.7     2.20     113.7    5.58  0.1766  0.1759
#===============================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
Attempted anisotropic refinement leads to multiple non-positive definite
atoms. The S atoms were refined anisotropically, since this improved the
R-factors quite significantly, but ISOR restraints were required to prevent
unreasonably oblate ellipsoids. Adding ADPs with ISOR restraints seemed to
be of minimal value - hence the C,O,N atoms were left as isotropic.

The H atoms of the NH2 group could not readily be refined, so they were
placed in-plane and allowed to ride. This is an approximation.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2422
_refine_ls_number_parameters     108
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1551
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.813
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.123

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.0015(2) 0.37265(8) 0.02099(13) 0.0152(4) Uani 1 1 d . U . . .
S12 S 0.0875(2) 0.49157(8) 0.18324(14) 0.0182(4) Uani 1 1 d . U . . .
O11 O 0.0049(6) 0.33628(19) -0.0745(3) 0.0181(10) Uiso 1 1 d . . . . .
O12 O -0.1860(6) 0.41565(19) 0.0270(3) 0.0163(10) Uiso 1 1 d . . . . .
N11 N -0.0194(8) 0.1879(3) 0.3673(4) 0.0226(13) Uiso 1 1 d . . . . .
H10 H 0.090808 0.161008 0.380489 0.034 Uiso 1 1 calc R U . . .
H11 H -0.135051 0.186974 0.405211 0.034 Uiso 1 1 calc R U . . .
N12 N 0.2361(7) 0.4090(2) 0.0333(4) 0.0121(11) Uiso 1 1 d . . . . .
N13 N 0.4741(7) 0.4793(2) 0.1233(4) 0.0152(12) Uiso 1 1 d . . . . .
H17 H 0.589083 0.466445 0.090521 0.023 Uiso 1 1 calc R U . . .
C11 C -0.0112(9) 0.2305(3) 0.2896(5) 0.0134(14) Uiso 1 1 d . . . . .
C12 C 0.1668(10) 0.2349(3) 0.2262(5) 0.0172(15) Uiso 1 1 d . . . . .
H12 H 0.288176 0.206395 0.238467 0.021 Uiso 1 1 calc R U . . .
C13 C 0.1734(10) 0.2779(3) 0.1484(5) 0.0175(15) Uiso 1 1 d . . . . .
H13 H 0.298599 0.279310 0.107792 0.021 Uiso 1 1 calc R U . . .
C14 C -0.0007(9) 0.3200(3) 0.1269(5) 0.0125(14) Uiso 1 1 d . . . . .
C15 C -0.1847(10) 0.3172(3) 0.1867(5) 0.0157(14) Uiso 1 1 d . . . . .
H15 H -0.306161 0.345442 0.172272 0.019 Uiso 1 1 calc R U . . .
C16 C -0.1893(10) 0.2737(3) 0.2660(5) 0.0204(16) Uiso 1 1 d . . . . .
H16 H -0.314785 0.272347 0.306359 0.024 Uiso 1 1 calc R U . . .
C17 C 0.2696(9) 0.4530(3) 0.1043(5) 0.0136(14) Uiso 1 1 d . . . . .
C18 C 0.4909(10) 0.5268(3) 0.1964(5) 0.0177(15) Uiso 1 1 d . . . . .
H18 H 0.625672 0.548703 0.215664 0.021 Uiso 1 1 calc R U . . .
C19 C 0.3014(10) 0.5395(3) 0.2379(5) 0.0215(16) Uiso 1 1 d . . . . .
H19 H 0.284442 0.570595 0.290581 0.026 Uiso 1 1 calc R U . . .
S30 S 0.9233(3) 0.60150(8) 0.45598(14) 0.0245(5) Uani 1 1 d . U . . .
O30 O 0.8774(8) 0.5841(2) 0.3486(4) 0.0414(14) Uiso 1 1 d . . . . .
O31 O 1.1434(8) 0.5900(3) 0.4995(4) 0.0502(15) Uiso 1 1 d . . . . .
C30 C 0.7282(12) 0.5653(4) 0.5363(6) 0.038(2) Uiso 1 1 d . . . . .
H30A H 0.599923 0.547680 0.492823 0.045 Uiso 1 1 calc R U . . .
H30B H 0.799094 0.530822 0.579629 0.045 Uiso 1 1 calc R U . . .
C31 C 0.6566(10) 0.6191(3) 0.6042(5) 0.0236(16) Uiso 1 1 d . . . . .
H31A H 0.512702 0.608967 0.632582 0.028 Uiso 1 1 calc R U . . .
H31B H 0.768795 0.626473 0.663531 0.028 Uiso 1 1 calc R U . . .
C32 C 0.6348(11) 0.6758(3) 0.5362(6) 0.0315(18) Uiso 1 1 d . . . . .
H32A H 0.618768 0.714469 0.579173 0.038 Uiso 1 1 calc R U . . .
H32B H 0.501713 0.671938 0.486285 0.038 Uiso 1 1 calc R U . . .
C33 C 0.8439(11) 0.6806(3) 0.4765(6) 0.0282(17) Uiso 1 1 d . . . . .
H33A H 0.962646 0.703878 0.518302 0.034 Uiso 1 1 calc R U . . .
H33B H 0.811737 0.702861 0.408840 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.442(4) . ?
S11 O12 1.455(4) . ?
S11 N12 1.606(5) . ?
S11 C14 1.750(6) . ?
S12 C19 1.741(7) . ?
S12 C17 1.749(6) . ?
N11 C11 1.342(8) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.300(7) . ?
N13 C17 1.357(7) . ?
N13 C18 1.368(8) . ?
N13 H17 0.8800 . ?
C11 C12 1.399(8) . ?
C11 C16 1.422(8) . ?
C12 C13 1.347(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(8) . ?
C15 C16 1.367(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.325(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S30 O31 1.421(5) . ?
S30 O30 1.428(5) . ?
S30 C33 1.756(7) . ?
S30 C30 1.791(7) . ?
C30 C31 1.508(9) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.476(9) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.528(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 115.9(2) . . ?
O11 S11 N12 105.4(2) . . ?
O12 S11 N12 112.5(3) . . ?
O11 S11 C14 108.8(3) . . ?
O12 S11 C14 107.4(2) . . ?
N12 S11 C14 106.5(3) . . ?
C19 S12 C17 91.2(3) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 119.7(4) . . ?
C17 N13 C18 116.0(5) . . ?
C17 N13 H17 122.0 . . ?
C18 N13 H17 122.0 . . ?
N11 C11 C12 123.2(5) . . ?
N11 C11 C16 120.9(5) . . ?
C12 C11 C16 115.9(6) . . ?
C13 C12 C11 122.7(6) . . ?
C13 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C12 C13 C14 120.7(6) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 119.2(6) . . ?
C13 C14 S11 120.4(4) . . ?
C15 C14 S11 120.3(5) . . ?
C16 C15 C14 119.8(6) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.8(6) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
N12 C17 N13 120.3(5) . . ?
N12 C17 S12 131.5(4) . . ?
N13 C17 S12 108.2(4) . . ?
C19 C18 N13 113.6(6) . . ?
C19 C18 H18 123.2 . . ?
N13 C18 H18 123.2 . . ?
C18 C19 S12 111.1(5) . . ?
C18 C19 H19 124.5 . . ?
S12 C19 H19 124.5 . . ?
O31 S30 O30 116.1(3) . . ?
O31 S30 C33 111.1(3) . . ?
O30 S30 C33 110.6(3) . . ?
O31 S30 C30 109.8(4) . . ?
O30 S30 C30 110.9(3) . . ?
C33 S30 C30 96.7(3) . . ?
C31 C30 S30 104.1(5) . . ?
C31 C30 H30A 110.9 . . ?
S30 C30 H30A 110.9 . . ?
C31 C30 H30B 110.9 . . ?
S30 C30 H30B 110.9 . . ?
H30A C30 H30B 109.0 . . ?
C32 C31 C30 106.4(6) . . ?
C32 C31 H31A 110.4 . . ?
C30 C31 H31A 110.4 . . ?
C32 C31 H31B 110.4 . . ?
C30 C31 H31B 110.4 . . ?
H31A C31 H31B 108.6 . . ?
C31 C32 C33 108.0(6) . . ?
C31 C32 H32A 110.1 . . ?
C33 C32 H32A 110.1 . . ?
C31 C32 H32B 110.1 . . ?
C33 C32 H32B 110.1 . . ?
H32A C32 H32B 108.4 . . ?
C32 C33 S30 105.0(5) . . ?
C32 C33 H33A 110.8 . . ?
S30 C33 H33A 110.8 . . ?
C32 C33 H33B 110.8 . . ?
S30 C33 H33B 110.8 . . ?
H33A C33 H33B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 169.9(5) . . . . ?
O12 S11 N12 C17 42.8(6) . . . . ?
C14 S11 N12 C17 -74.6(5) . . . . ?
N11 C11 C12 C13 -179.9(6) . . . . ?
C16 C11 C12 C13 1.1(9) . . . . ?
C11 C12 C13 C14 -0.6(10) . . . . ?
C12 C13 C14 C15 -0.4(10) . . . . ?
C12 C13 C14 S11 -176.3(5) . . . . ?
O11 S11 C14 C13 61.1(6) . . . . ?
O12 S11 C14 C13 -172.8(5) . . . . ?
N12 S11 C14 C13 -52.0(6) . . . . ?
O11 S11 C14 C15 -114.8(5) . . . . ?
O12 S11 C14 C15 11.3(6) . . . . ?
N12 S11 C14 C15 132.1(5) . . . . ?
C13 C14 C15 C16 0.8(9) . . . . ?
S11 C14 C15 C16 176.8(5) . . . . ?
C14 C15 C16 C11 -0.3(10) . . . . ?
N11 C11 C16 C15 -179.6(6) . . . . ?
C12 C11 C16 C15 -0.6(9) . . . . ?
S11 N12 C17 N13 172.9(4) . . . . ?
S11 N12 C17 S12 -10.9(9) . . . . ?
C18 N13 C17 N12 177.6(6) . . . . ?
C18 N13 C17 S12 0.5(7) . . . . ?
C19 S12 C17 N12 -177.5(7) . . . . ?
C19 S12 C17 N13 -0.9(5) . . . . ?
C17 N13 C18 C19 0.3(8) . . . . ?
N13 C18 C19 S12 -1.1(7) . . . . ?
C17 S12 C19 C18 1.2(5) . . . . ?
O31 S30 C30 C31 97.6(5) . . . . ?
O30 S30 C30 C31 -132.8(5) . . . . ?
C33 S30 C30 C31 -17.8(6) . . . . ?
S30 C30 C31 C32 39.6(6) . . . . ?
C30 C31 C32 C33 -48.0(7) . . . . ?
C31 C32 C33 S30 33.1(7) . . . . ?
O31 S30 C33 C32 -122.4(5) . . . . ?
O30 S30 C33 C32 107.2(5) . . . . ?
C30 S30 C33 C32 -8.1(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.88 2.52 3.235(6) 138.6 4_666 yes
N11 H11 S11 0.88 3.01 3.837(5) 156.7 4_566 yes
N11 H11 O11 0.88 2.26 3.064(6) 151.4 4_566 yes
N13 H17 O12 0.88 1.95 2.811(6) 164.7 1_655 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11
_database_code_depnum_ccdc_archive 'CCDC 2120773'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 12o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_11                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.10 angstrom. Data were integrated to 0.84
angstrom, but truncated at 0.95 angstrom resolution. This remains optimistic,
since < 50% of the data are observed at the 2sigma level. The structure is
clearly of limited precision, particularly for the solvent, but it remains of
value in the context of the set of structures with which it is published.
The coordinates also provide a suitable starting set for optimisation by
DFT-D methods.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, methylisoxazole (1:1) solvate'
_chemical_name_common            'Sulfathiazole, methylisoxazole solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H5 N O'
_chemical_formula_sum            'C13 H14 N4 O3 S2'
_chemical_formula_weight         338.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.366(2)
_cell_length_b                   21.353(4)
_cell_length_c                   9.097(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.37(3)
_cell_angle_gamma                90
_cell_volume                     1622.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5049
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      21.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.345
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5049
_diffrn_reflns_av_unetI/netI     0.1723
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.907
_diffrn_reflns_theta_max         21.960
_diffrn_reflns_theta_full        21.960
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.952
_reflns_number_total             1891
_reflns_number_gt                852
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  12o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.71      36     42     85.7     3.29     890.0   56.19  0.1601  0.0128
3.71 - 2.46      84     85     98.8     3.13     368.4   24.48  0.1066  0.0304
2.46 - 1.96     119    121     98.3     3.00     137.7   11.37  0.0601  0.0676
1.96 - 1.70     121    124     97.6     2.85     104.9    7.70  0.0642  0.0890
1.70 - 1.54     118    122     96.7     2.96      64.0    6.01  0.0649  0.1281
1.54 - 1.43     118    120     98.3     2.73      52.0    4.55  0.0704  0.1734
1.43 - 1.34     130    132     98.5     2.86      40.7    4.00  0.0758  0.2054
1.34 - 1.27     118    125     94.4     2.70      35.4    3.39  0.0880  0.2456
1.27 - 1.21     132    137     96.4     2.67      33.8    3.17  0.1034  0.2815
1.21 - 1.17      98    101     97.0     2.62      32.2    2.50  0.1132  0.3094
1.17 - 1.13     118    126     93.7     2.41      26.5    2.26  0.1222  0.3848
1.13 - 1.09     129    133     97.0     2.49      24.2    2.16  0.1407  0.4310
1.09 - 1.06     108    122     88.5     2.09      21.9    1.76  0.1422  0.4983
1.06 - 1.02     161    178     90.4     1.94      13.2    1.19  0.1918  0.7834
1.02 - 1.00      80     97     82.5     1.64      10.3    0.89  0.2469  1.1070
1.00 - 0.97     147    160     91.9     1.89      10.0    0.88  0.2584  1.0826
0.97 - 0.95     118    137     86.1     1.85       7.0    0.68  0.2889  1.5113
0.95 - 0.93     100    112     89.3     1.84       8.1    0.76  0.2521  1.3852
0.93 - 0.91     123    151     81.5     1.45       6.5    0.56  0.2644  1.7967
0.91 - 0.88     144    258     55.8     0.83       5.6    0.44  0.2510  2.3293
0.88 - 0.85      76    263     28.9     0.35       4.9    0.33  0.2789  3.0485
0.85 - 0.84       6    130      4.6     0.05       3.9    0.24  0.0000  4.4255
#------------------------------------------------------------------------------
0.94 - 0.84     394    854     46.1     0.74       5.9    0.48  0.2603  2.1549
 Inf - 0.84    2384   2976     80.1     1.96      58.5    4.46  0.1126  0.1778
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1891
_refine_ls_number_parameters     183
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_restrained_S_all      0.787
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.056

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.54575(19) 0.14252(8) 0.3807(2) 0.0595(6) Uani 1 1 d . . . . .
S12 S 0.6577(3) 0.13654(10) 0.7338(2) 0.1150(9) Uani 1 1 d . . . . .
O11 O 0.5318(5) 0.12158(19) 0.2299(4) 0.0705(13) Uani 1 1 d . . . . .
O12 O 0.6793(5) 0.18232(19) 0.4260(5) 0.0735(14) Uani 1 1 d . . . . .
N11 N -0.0528(6) 0.2691(3) 0.5157(7) 0.091(2) Uani 1 1 d . . . . .
H10 H -0.051588 0.300814 0.577618 0.137 Uiso 1 1 calc R U . . .
H11 H -0.144358 0.255658 0.474701 0.137 Uiso 1 1 calc R U . . .
N12 N 0.5460(5) 0.0785(2) 0.4748(6) 0.0557(14) Uani 1 1 d . . . . .
N13 N 0.5773(6) 0.0249(2) 0.6935(6) 0.0686(16) Uani 1 1 d . . . . .
H17 H 0.543431 -0.010278 0.652159 0.103 Uiso 1 1 calc R U . . .
C11 C 0.0863(8) 0.2411(3) 0.4833(7) 0.0583(18) Uani 1 1 d . . . . .
C12 C 0.0845(7) 0.1926(3) 0.3819(7) 0.0628(19) Uani 1 1 d . . . . .
H12 H -0.014267 0.179265 0.335309 0.075 Uiso 1 1 calc R U . . .
C13 C 0.2243(8) 0.1636(3) 0.3483(7) 0.0607(18) Uani 1 1 d . . . . .
H13 H 0.221373 0.129956 0.279717 0.073 Uiso 1 1 calc R U . . .
C14 C 0.3700(7) 0.1832(3) 0.4141(7) 0.0514(17) Uani 1 1 d . . . . .
C15 C 0.3719(8) 0.2319(3) 0.5138(7) 0.0622(18) Uani 1 1 d . . . . .
H15 H 0.470485 0.245398 0.560606 0.075 Uiso 1 1 calc R U . . .
C16 C 0.2308(9) 0.2612(3) 0.5458(8) 0.0652(19) Uani 1 1 d . . . . .
H16 H 0.233727 0.295726 0.611810 0.078 Uiso 1 1 calc R U . . .
C17 C 0.5870(7) 0.0781(3) 0.6165(8) 0.0606(18) Uani 1 1 d . . . . .
C18 C 0.6229(10) 0.0284(4) 0.8403(8) 0.103(3) Uani 1 1 d . . . . .
H18 H 0.623106 -0.006299 0.905587 0.123 Uiso 1 1 calc R U . . .
C19 C 0.6666(12) 0.0855(4) 0.8809(9) 0.135(4) Uani 1 1 d . . . . .
H19 H 0.699035 0.097066 0.979046 0.161 Uiso 1 1 calc R U . . .
O30 O 0.1277(9) 0.0523(6) 0.9256(13) 0.173(2) Uiso 0.762(7) 1 d D U P A 1
N30 N 0.1363(10) 0.1182(7) 0.9523(15) 0.173(2) Uiso 0.762(7) 1 d D U P A 1
C31 C 0.1311(11) 0.1404(8) 0.828(2) 0.173(2) Uiso 0.762(7) 1 d D U P A 1
H31 H 0.134412 0.184002 0.807626 0.208 Uiso 0.762(7) 1 calc R U P A 1
C32 C 0.1201(11) 0.0955(9) 0.7260(18) 0.173(2) Uiso 0.762(7) 1 d D U P A 1
H32 H 0.114632 0.103056 0.622898 0.208 Uiso 0.762(7) 1 calc R U P A 1
C33 C 0.1180(9) 0.0434(11) 0.782(2) 0.173(2) Uiso 0.762(7) 1 d D U P A 1
C34 C 0.1084(15) -0.0236(7) 0.7409(17) 0.173(2) Uiso 0.762(7) 1 d D U P A 1
H34A H 0.111166 -0.049277 0.830339 0.260 Uiso 0.762(7) 1 calc R U P A 1
H34B H 0.008235 -0.031470 0.682399 0.260 Uiso 0.762(7) 1 calc R U P A 1
H34C H 0.199385 -0.034583 0.682798 0.260 Uiso 0.762(7) 1 calc R U P A 1
O30A O 0.097(3) 0.0159(13) 0.850(3) 0.173(2) Uiso 0.238(7) 1 d D U P A 2
N30A N 0.028(3) -0.0358(12) 0.768(4) 0.173(2) Uiso 0.238(7) 1 d D U P A 2
C31A C 0.056(3) -0.0223(16) 0.642(4) 0.173(2) Uiso 0.238(7) 1 d D U P A 2
H31A H 0.025097 -0.047265 0.558298 0.208 Uiso 0.238(7) 1 calc R U P A 2
C32A C 0.134(3) 0.0319(15) 0.635(3) 0.173(2) Uiso 0.238(7) 1 d D U P A 2
H32A H 0.166408 0.050374 0.546651 0.208 Uiso 0.238(7) 1 calc R U P A 2
C33A C 0.159(3) 0.0549(17) 0.758(4) 0.173(2) Uiso 0.238(7) 1 d D U P A 2
C34A C 0.232(5) 0.1100(16) 0.834(5) 0.173(2) Uiso 0.238(7) 1 d D U P A 2
H34D H 0.276965 0.137906 0.761830 0.260 Uiso 0.238(7) 1 d R U P A 2
H34E H 0.317915 0.095766 0.904570 0.260 Uiso 0.238(7) 1 d R U P A 2
H34F H 0.151134 0.132496 0.887090 0.260 Uiso 0.238(7) 1 d R U P A 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.442(4) . ?
S11 O12 1.444(4) . ?
S11 N12 1.613(5) . ?
S11 C14 1.750(6) . ?
S12 C17 1.724(7) . ?
S12 C19 1.724(8) . ?
N11 C11 1.357(7) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.315(7) . ?
N13 C17 1.339(7) . ?
N13 C18 1.369(8) . ?
N13 H17 0.8800 . ?
C11 C16 1.374(8) . ?
C11 C12 1.387(8) . ?
C12 C13 1.373(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(8) . ?
C15 C16 1.382(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.319(10) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C33 1.320(16) . ?
O30 N30 1.427(13) . ?
N30 C31 1.222(16) . ?
C31 C32 1.337(17) . ?
C31 H31 0.9500 . ?
C32 C33 1.223(19) . ?
C32 H32 0.9500 . ?
C33 C34 1.48(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
O30A C33A 1.313(18) . ?
O30A N30A 1.431(16) . ?
N30A C31A 1.223(18) . ?
C31A C32A 1.333(19) . ?
C31A H31A 0.9500 . ?
C32A C33A 1.22(2) . ?
C32A H32A 0.9500 . ?
C33A C34A 1.48(2) . ?
C34A H34D 0.9800 . ?
C34A H34E 0.9801 . ?
C34A H34F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.1(3) . . ?
O11 S11 N12 103.9(3) . . ?
O12 S11 N12 111.8(3) . . ?
O11 S11 C14 107.3(3) . . ?
O12 S11 C14 107.6(3) . . ?
N12 S11 C14 107.7(2) . . ?
C17 S12 C19 91.2(4) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 121.2(5) . . ?
C17 N13 C18 116.2(6) . . ?
C17 N13 H17 121.9 . . ?
C18 N13 H17 121.9 . . ?
N11 C11 C16 121.2(6) . . ?
N11 C11 C12 119.9(6) . . ?
C16 C11 C12 118.9(6) . . ?
C13 C12 C11 120.6(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.3(6) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.1(6) . . ?
C15 C14 S11 120.7(5) . . ?
C13 C14 S11 120.0(5) . . ?
C14 C15 C16 120.2(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.9(6) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N12 C17 N13 119.9(6) . . ?
N12 C17 S12 131.5(6) . . ?
N13 C17 S12 108.6(5) . . ?
C19 C18 N13 112.4(7) . . ?
C19 C18 H18 123.8 . . ?
N13 C18 H18 123.8 . . ?
C18 C19 S12 111.6(7) . . ?
C18 C19 H19 124.2 . . ?
S12 C19 H19 124.2 . . ?
C33 O30 N30 108.1(14) . . ?
C31 N30 O30 103.2(13) . . ?
N30 C31 C32 111.1(16) . . ?
N30 C31 H31 124.4 . . ?
C32 C31 H31 124.4 . . ?
C33 C32 C31 111.5(18) . . ?
C33 C32 H32 124.3 . . ?
C31 C32 H32 124.3 . . ?
C32 C33 O30 106(2) . . ?
C32 C33 C34 141(2) . . ?
O30 C33 C34 112.8(18) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33A O30A N30A 108.6(16) . . ?
C31A N30A O30A 102.5(16) . . ?
N30A C31A C32A 111.5(19) . . ?
N30A C31A H31A 124.2 . . ?
C32A C31A H31A 124.2 . . ?
C33A C32A C31A 111(2) . . ?
C33A C32A H32A 124.3 . . ?
C31A C32A H32A 124.3 . . ?
C32A C33A O30A 106(2) . . ?
C32A C33A C34A 142(3) . . ?
O30A C33A C34A 112(2) . . ?
C33A C34A H34D 109.3 . . ?
C33A C34A H34E 109.2 . . ?
H34D C34A H34E 109.5 . . ?
C33A C34A H34F 109.9 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 167.1(5) . . . . ?
O12 S11 N12 C17 38.6(5) . . . . ?
C14 S11 N12 C17 -79.3(5) . . . . ?
N11 C11 C12 C13 -179.8(6) . . . . ?
C16 C11 C12 C13 2.3(10) . . . . ?
C11 C12 C13 C14 -0.9(9) . . . . ?
C12 C13 C14 C15 0.2(9) . . . . ?
C12 C13 C14 S11 175.5(5) . . . . ?
O11 S11 C14 C15 -149.2(5) . . . . ?
O12 S11 C14 C15 -21.1(6) . . . . ?
N12 S11 C14 C15 99.6(5) . . . . ?
O11 S11 C14 C13 35.6(5) . . . . ?
O12 S11 C14 C13 163.8(5) . . . . ?
N12 S11 C14 C13 -75.6(5) . . . . ?
C13 C14 C15 C16 -0.9(9) . . . . ?
S11 C14 C15 C16 -176.1(5) . . . . ?
N11 C11 C16 C15 179.2(6) . . . . ?
C12 C11 C16 C15 -3.0(10) . . . . ?
C14 C15 C16 C11 2.3(10) . . . . ?
S11 N12 C17 N13 176.2(4) . . . . ?
S11 N12 C17 S12 -4.3(8) . . . . ?
C18 N13 C17 N12 179.7(6) . . . . ?
C18 N13 C17 S12 0.0(7) . . . . ?
C19 S12 C17 N12 179.5(7) . . . . ?
C19 S12 C17 N13 -0.9(6) . . . . ?
C17 N13 C18 C19 1.2(11) . . . . ?
N13 C18 C19 S12 -1.9(11) . . . . ?
C17 S12 C19 C18 1.6(8) . . . . ?
C33 O30 N30 C31 0.0(3) . . . . ?
O30 N30 C31 C32 0.0(3) . . . . ?
N30 C31 C32 C33 0.0(6) . . . . ?
C31 C32 C33 O30 0.0(7) . . . . ?
C31 C32 C33 C34 180.0(7) . . . . ?
N30 O30 C33 C32 0.0(5) . . . . ?
N30 O30 C33 C34 180.0(4) . . . . ?
C33A O30A N30A C31A 0.0(3) . . . . ?
O30A N30A C31A C32A 0.1(3) . . . . ?
N30A C31A C32A C33A -0.1(6) . . . . ?
C31A C32A C33A O30A 0.1(7) . . . . ?
C31A C32A C33A C34A -179.9(8) . . . . ?
N30A O30A C33A C32A -0.1(6) . . . . ?
N30A O30A C33A C34A 179.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.88 2.24 3.095(7) 162.6 4_566 yes
N11 H11 O12 0.88 2.18 2.985(7) 152.0 1_455 yes
N13 H17 S11 0.88 2.93 3.771(6) 160.1 3_656 yes
N13 H17 N12 0.88 1.98 2.846(7) 168.5 3_656 yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_18
_database_code_depnum_ccdc_archive 'CCDC 2120780'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 19o
#===============================================================================
# start Validation Reply Form
_vrf_PLAT029_18                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.935 Why?  
RESPONSE: The data are measured with a point-detector instrument. The missing
data are uniformly distributed over the resolution shells beyond ca 1.6 
angstrom and there is no systematic omission of high-angle data (for example).
There is no indication of any adverse effect on the refined structure.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, (+/-) 5-methyldihydrofuran-2-one (1:1) solvate'
_chemical_name_common            'Sulfathiazole, gamma-valerolactone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C5 H8 O2'
_chemical_formula_sum            'C14 H17 N3 O4 S2'
_chemical_formula_weight         355.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.417(2)
_cell_length_b                   20.975(4)
_cell_length_c                   9.472(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.83(3)
_cell_angle_gamma                90
_cell_volume                     1668.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      4.22
_cell_measurement_theta_max      66.59

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.103
_shelx_estimated_absorpt_T_min   0.576
_shelx_estimated_absorpt_T_max   0.576
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            2941
_diffrn_reflns_av_unetI/netI     0.0921
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.215
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_full        66.589
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.935
_reflns_number_total             2751
_reflns_number_gt                1507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  19o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.74      43     43    100.0     1.23     896.5   39.23  0.0278  0.0153
3.74 - 2.38      99    100     99.0     1.12     404.4   27.44  0.0357  0.0234
2.38 - 1.87     146    146    100.0     1.12     174.7   20.31  0.0538  0.0365
1.87 - 1.63     138    142     97.2     1.07     125.6   15.93  0.0426  0.0461
1.63 - 1.48     139    146     95.2     1.03      90.2   14.25  0.0260  0.0598
1.48 - 1.36     151    156     96.8     1.03      72.3   12.01  0.0454  0.0741
1.36 - 1.28     140    149     94.0     1.03      45.0    8.01  0.0558  0.1286
1.28 - 1.21     140    149     94.0     1.00      54.9    8.91  0.0308  0.1038
1.21 - 1.16     134    144     93.1     0.99      56.2    8.38  0.0551  0.1054
1.16 - 1.11     149    164     90.9     0.95      34.8    6.03  0.0978  0.1852
1.11 - 1.07     138    149     92.6     0.97      30.0    5.23  0.0768  0.2368
1.07 - 1.03     168    180     93.3     1.00      24.1    4.49  0.1418  0.2531
1.03 - 1.00     136    158     86.1     0.92      15.6    3.35  0.2205  0.3845
1.00 - 0.97     145    170     85.3     0.91      11.9    2.70  0.0943  0.5115
0.97 - 0.94     150    174     86.2     0.91      10.9    2.41  0.2235  0.5477
0.94 - 0.92     143    163     87.7     0.92       9.0    2.15  0.0820  0.6439
0.92 - 0.90     160    169     94.7     0.99       7.6    1.93  0.0693  0.7732
0.90 - 0.88     143    151     94.7     0.99       6.4    1.72  0.3012  0.8363
0.88 - 0.87      87     91     95.6     0.99       5.9    1.59  0.2075  0.9665
0.87 - 0.85     183    196     93.4     0.97       4.6    1.17  0.3623  1.1992
0.85 - 0.84     102    104     98.1     1.02       4.6    1.35  0.0538  1.1086
#------------------------------------------------------------------------------
0.94 - 0.84     818    874     93.6     0.98       6.4    1.65  0.1404  0.8695
 Inf - 0.84    2834   3044     93.1     1.00      67.2    7.69  0.0400  0.0909
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2751
_refine_ls_number_parameters     253
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.050

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.55862(12) 0.14570(4) 0.40055(9) 0.0506(3) Uani 1 1 d . . . . .
S12 S 0.6372(2) 0.13583(5) 0.74582(12) 0.1142(6) Uani 1 1 d . . . . .
O11 O 0.5481(3) 0.12515(10) 0.2545(2) 0.0598(7) Uani 1 1 d . . . . .
O12 O 0.6939(3) 0.18344(11) 0.4512(3) 0.0670(8) Uani 1 1 d . . . . .
N11 N -0.0359(4) 0.27513(15) 0.5263(4) 0.0747(10) Uani 1 1 d . . . . .
H10 H -0.035335 0.306437 0.584998 0.112 Uiso 1 1 d R U . . .
H11 H -0.124535 0.261687 0.486648 0.112 Uiso 1 1 d R U . . .
N12 N 0.5514(3) 0.07938(12) 0.4867(3) 0.0471(7) Uani 1 1 d . . . . .
N13 N 0.5743(4) 0.02097(13) 0.6927(3) 0.0613(9) Uani 1 1 d . . . . .
H17 H 0.548896 -0.013868 0.648903 0.074 Uiso 1 1 calc R U . . .
C11 C 0.1024(5) 0.24704(15) 0.4965(4) 0.0498(9) Uani 1 1 d . . . . .
C12 C 0.1019(5) 0.19752(17) 0.3976(4) 0.0560(10) Uani 1 1 d . . . . .
H12 H 0.005866 0.184235 0.352817 0.067 Uiso 1 1 calc R U . . .
C13 C 0.2405(4) 0.16827(16) 0.3658(4) 0.0510(9) Uani 1 1 d . . . . .
H13 H 0.237720 0.135453 0.299623 0.061 Uiso 1 1 calc R U . . .
C14 C 0.3856(4) 0.18737(15) 0.4317(3) 0.0443(8) Uani 1 1 d . . . . .
C15 C 0.3891(4) 0.23780(15) 0.5276(4) 0.0509(9) Uani 1 1 d . . . . .
H15 H 0.485553 0.251558 0.570694 0.061 Uiso 1 1 calc R U . . .
C16 C 0.2493(5) 0.26722(16) 0.5584(4) 0.0556(10) Uani 1 1 d . . . . .
H16 H 0.252627 0.301191 0.621641 0.067 Uiso 1 1 calc R U . . .
C17 C 0.5842(4) 0.07701(16) 0.6251(4) 0.0550(10) Uani 1 1 d . . . . .
C18 C 0.6077(7) 0.0232(2) 0.8365(4) 0.0963(17) Uani 1 1 d . . . . .
H18 H 0.606389 -0.012342 0.895061 0.116 Uiso 1 1 calc R U . . .
C19 C 0.6418(8) 0.0814(2) 0.8828(5) 0.129(2) Uani 1 1 d . . . . .
H19 H 0.665422 0.091776 0.977319 0.155 Uiso 1 1 calc R U . . .
O30 O 0.1847(17) 0.0401(9) 0.8813(17) 0.118(5) Uani 0.5 1 d . U P A 1
O31 O 0.1300(16) 0.1287(8) 1.0415(19) 0.125(5) Uani 0.5 1 d . U P A 1
C30 C 0.1483(7) 0.1027(3) 0.9254(6) 0.0870(15) Uani 0.5 1 d . . P A 1
C31 C 0.1660(17) 0.1285(7) 0.7866(15) 0.106(5) Uani 0.5 1 d . U P A 1
H31A H 0.270866 0.147124 0.780857 0.127 Uiso 0.5 1 calc R U P A 1
H31B H 0.086441 0.161078 0.764181 0.127 Uiso 0.5 1 calc R U P A 1
C32 C 0.1437(15) 0.0730(7) 0.6869(12) 0.092(3) Uani 0.5 1 d . U P A 1
H32A H 0.036875 0.073824 0.641580 0.111 Uiso 0.5 1 calc R U P A 1
H32B H 0.218775 0.076033 0.613820 0.111 Uiso 0.5 1 calc R U P A 1
C33 C 0.1658(15) 0.0205(6) 0.7553(15) 0.088(3) Uani 0.5 1 d . U P A 1
H33A H 0.273236 0.007633 0.733175 0.105 Uiso 0.5 1 calc R U P A 1
C34 C 0.0740(8) -0.0340(3) 0.7231(7) 0.143(2) Uani 0.5 1 d . . P A 1
H34A H 0.072002 -0.042217 0.623266 0.215 Uiso 0.5 1 calc R U P A 1
H34B H 0.119835 -0.069926 0.773850 0.215 Uiso 0.5 1 calc R U P A 1
H34C H -0.032633 -0.027320 0.750086 0.215 Uiso 0.5 1 calc R U P A 1
O30A O 0.1218(14) 0.0404(6) 0.9150(11) 0.073(3) Uani 0.5 1 d . . P B 2
O31A O 0.2117(14) 0.1190(7) 1.0353(18) 0.102(4) Uani 0.5 1 d . U P B 2
C30A C 0.1483(7) 0.1027(3) 0.9254(6) 0.0870(15) Uani 0.5 1 d . . P B 2
C31A C 0.0750(16) 0.1403(6) 0.8070(13) 0.092(4) Uani 0.5 1 d . U P B 2
H31C H 0.147408 0.172781 0.776865 0.111 Uiso 0.5 1 calc R U P B 2
H31D H -0.022744 0.160387 0.832620 0.111 Uiso 0.5 1 calc R U P B 2
C32A C 0.0424(17) 0.0905(5) 0.6928(12) 0.095(4) Uani 0.5 1 d . U P B 2
H32C H -0.062666 0.096346 0.646019 0.114 Uiso 0.5 1 calc R U P B 2
H32D H 0.120959 0.092839 0.622571 0.114 Uiso 0.5 1 calc R U P B 2
C33A C 0.052(2) 0.0330(7) 0.7627(14) 0.124(4) Uani 0.5 1 d . U P B 2
H33B H -0.060112 0.029963 0.783796 0.149 Uiso 0.5 1 calc R U P B 2
C34A C 0.0740(8) -0.0340(3) 0.7231(7) 0.143(2) Uani 0.5 1 d . . P B 2
H34D H 0.073924 -0.060320 0.806072 0.215 Uiso 0.5 1 calc R U P B 2
H34E H -0.011281 -0.046860 0.656804 0.215 Uiso 0.5 1 calc R U P B 2
H34F H 0.173720 -0.038731 0.680552 0.215 Uiso 0.5 1 calc R U P B 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.442(2) . ?
S11 O11 1.446(2) . ?
S11 N12 1.616(3) . ?
S11 C14 1.740(3) . ?
S12 C17 1.720(4) . ?
S12 C19 1.726(5) . ?
N11 C11 1.352(4) . ?
N11 H10 0.8600 . ?
N11 H11 0.8601 . ?
N12 C17 1.323(4) . ?
N13 C17 1.343(4) . ?
N13 C18 1.374(5) . ?
N13 H17 0.8600 . ?
C11 C16 1.398(5) . ?
C11 C12 1.398(5) . ?
C12 C13 1.370(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(4) . ?
C15 C16 1.377(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.322(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O30 C33 1.263(17) . ?
O30 C30 1.416(18) . ?
O31 C30 1.247(17) . ?
C30 C31 1.439(14) . ?
C31 C32 1.503(17) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.285(16) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.402(13) . ?
C33 H33A 0.9800 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
O30A C30A 1.326(15) . ?
O30A C33A 1.529(17) . ?
O31A C30A 1.189(16) . ?
C30A C31A 1.472(13) . ?
C31A C32A 1.516(16) . ?
C31A H31C 0.9700 . ?
C31A H31D 0.9700 . ?
C32A C33A 1.375(17) . ?
C32A H32C 0.9700 . ?
C32A H32D 0.9700 . ?
C33A C34A 1.471(15) . ?
C33A H33B 0.9800 . ?
C34A H34D 0.9600 . ?
C34A H34E 0.9600 . ?
C34A H34F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 118.58(16) . . ?
O12 S11 N12 111.11(15) . . ?
O11 S11 N12 102.96(14) . . ?
O12 S11 C14 108.60(16) . . ?
O11 S11 C14 108.27(16) . . ?
N12 S11 C14 106.64(15) . . ?
C17 S12 C19 91.0(2) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 121.4(2) . . ?
C17 N13 C18 115.3(3) . . ?
C17 N13 H17 122.4 . . ?
C18 N13 H17 122.4 . . ?
N11 C11 C16 122.0(3) . . ?
N11 C11 C12 120.0(4) . . ?
C16 C11 C12 118.0(4) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 S11 120.7(3) . . ?
C13 C14 S11 119.9(3) . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.3(3) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
N12 C17 N13 119.3(3) . . ?
N12 C17 S12 131.3(3) . . ?
N13 C17 S12 109.4(3) . . ?
C19 C18 N13 112.7(4) . . ?
C19 C18 H18 123.6 . . ?
N13 C18 H18 123.6 . . ?
C18 C19 S12 111.6(3) . . ?
C18 C19 H19 124.2 . . ?
S12 C19 H19 124.2 . . ?
C33 O30 C30 124.4(14) . . ?
O31 C30 O30 135.1(11) . . ?
O31 C30 C31 131.8(11) . . ?
O30 C30 C31 92.4(9) . . ?
C30 C31 C32 105.4(10) . . ?
C30 C31 H31A 110.7 . . ?
C32 C31 H31A 110.7 . . ?
C30 C31 H31B 110.7 . . ?
C32 C31 H31B 110.7 . . ?
H31A C31 H31B 108.8 . . ?
C33 C32 C31 109.8(11) . . ?
C33 C32 H32A 109.7 . . ?
C31 C32 H32A 109.7 . . ?
C33 C32 H32B 109.7 . . ?
C31 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
O30 C33 C32 101.6(13) . . ?
O30 C33 C34 120.4(13) . . ?
C32 C33 C34 122.0(13) . . ?
O30 C33 H33A 103.4 . . ?
C32 C33 H33A 103.4 . . ?
C34 C33 H33A 103.4 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C30A O30A C33A 102.9(10) . . ?
O31A C30A O30A 114.3(10) . . ?
O31A C30A C31A 130.8(10) . . ?
O30A C30A C31A 114.3(8) . . ?
C30A C31A C32A 102.8(9) . . ?
C30A C31A H31C 111.2 . . ?
C32A C31A H31C 111.2 . . ?
C30A C31A H31D 111.2 . . ?
C32A C31A H31D 111.2 . . ?
H31C C31A H31D 109.1 . . ?
C33A C32A C31A 105.0(10) . . ?
C33A C32A H32C 110.8 . . ?
C31A C32A H32C 110.8 . . ?
C33A C32A H32D 110.8 . . ?
C31A C32A H32D 110.8 . . ?
H32C C32A H32D 108.8 . . ?
C32A C33A C34A 136.0(12) . . ?
C32A C33A O30A 111.8(11) . . ?
C34A C33A O30A 106.9(11) . . ?
C32A C33A H33B 97.4 . . ?
C34A C33A H33B 97.4 . . ?
O30A C33A H33B 97.4 . . ?
C33A C34A H34D 109.5 . . ?
C33A C34A H34E 109.5 . . ?
H34D C34A H34E 109.5 . . ?
C33A C34A H34F 109.5 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 40.7(3) . . . . ?
O11 S11 N12 C17 168.6(3) . . . . ?
C14 S11 N12 C17 -77.5(3) . . . . ?
N11 C11 C12 C13 -179.9(3) . . . . ?
C16 C11 C12 C13 2.1(5) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 C15 -1.8(5) . . . . ?
C12 C13 C14 S11 175.0(3) . . . . ?
O12 S11 C14 C15 -17.3(3) . . . . ?
O11 S11 C14 C15 -147.3(3) . . . . ?
N12 S11 C14 C15 102.5(3) . . . . ?
O12 S11 C14 C13 165.9(3) . . . . ?
O11 S11 C14 C13 35.9(3) . . . . ?
N12 S11 C14 C13 -74.3(3) . . . . ?
C13 C14 C15 C16 1.4(5) . . . . ?
S11 C14 C15 C16 -175.4(3) . . . . ?
C14 C15 C16 C11 0.8(5) . . . . ?
N11 C11 C16 C15 179.6(3) . . . . ?
C12 C11 C16 C15 -2.5(5) . . . . ?
S11 N12 C17 N13 179.0(3) . . . . ?
S11 N12 C17 S12 0.6(5) . . . . ?
C18 N13 C17 N12 -178.9(4) . . . . ?
C18 N13 C17 S12 -0.1(5) . . . . ?
C19 S12 C17 N12 178.1(4) . . . . ?
C19 S12 C17 N13 -0.4(4) . . . . ?
C17 N13 C18 C19 0.9(7) . . . . ?
N13 C18 C19 S12 -1.2(7) . . . . ?
C17 S12 C19 C18 0.9(5) . . . . ?
C33 O30 C30 O31 164.5(14) . . . . ?
C33 O30 C30 C31 -24.6(16) . . . . ?
O31 C30 C31 C32 -166.7(12) . . . . ?
O30 C30 C31 C32 22.0(12) . . . . ?
C30 C31 C32 C33 -19.7(15) . . . . ?
C30 O30 C33 C32 13.5(19) . . . . ?
C30 O30 C33 C34 -124.9(14) . . . . ?
C31 C32 C33 O30 5.0(16) . . . . ?
C31 C32 C33 C34 142.5(11) . . . . ?
C33A O30A C30A O31A -176.1(12) . . . . ?
C33A O30A C30A C31A 11.7(13) . . . . ?
O31A C30A C31A C32A 171.0(12) . . . . ?
O30A C30A C31A C32A -18.4(13) . . . . ?
C30A C31A C32A C33A 16.8(16) . . . . ?
C31A C32A C33A C34A -161.4(17) . . . . ?
C31A C32A C33A O30A -11.2(19) . . . . ?
C30A O30A C33A C32A 0.4(18) . . . . ?
C30A O30A C33A C34A 159.2(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H11 O12 0.86 2.25 3.027(4) 149.8 1_455 yes
N11 H10 O11 0.86 2.23 3.056(4) 160.7 4_566 yes
N13 H17 S11 0.86 2.94 3.758(3) 160.2 3_656 yes
N13 H17 O11 0.86 2.66 3.282(4) 130.8 3_656 yes
N13 H17 N12 0.86 2.03 2.863(4) 164.0 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 2120769'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 5o
#===============================================================================
# start Validation Reply Form
_vrf_PLAT430_4                   
;
PROBLEM: Short Inter D...A Contact  S22      ..O30      .       2.75 Ang.  
RESPONSE: This is a genuine intermolecular interaction, where the O atom
approaches the sigma-star orbital of the C---S bond (Rosenfield Jr.,
Parthasarathy & Dunitz, J. Am. Chem. Soc., 1977, 99, 4860).
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, N,N-dibutylformamide (2:1) solvate'
_chemical_name_common            'Sulfathiazole, N,N-dibutylformamide solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C9 H19 N O'
_chemical_formula_sum            'C27 H37 N7 O5 S4'
_chemical_formula_weight         667.87
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   16.616(3)
_cell_length_b                   16.088(3)
_cell_length_c                   12.630(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.69(3)
_cell_angle_gamma                90
_cell_volume                     3158.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13211
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.350
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13211
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.621
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.929
_reflns_number_total             6380
_reflns_number_gt                5655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     0.762
_reflns_Friedel_fraction_full    0.859

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  5o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.13      57     63     90.5     3.95     531.6   41.47  0.0202  0.0237
3.13 - 2.10     130    130    100.0     4.62     198.8   42.09  0.0276  0.0244
2.10 - 1.67     189    189    100.0     4.60     145.4   38.54  0.0302  0.0238
1.67 - 1.45     196    196    100.0     4.66      96.8   35.77  0.0372  0.0246
1.45 - 1.33     177    177    100.0     4.67      79.1   30.78  0.0410  0.0269
1.33 - 1.23     190    190    100.0     4.68      79.9   29.66  0.0427  0.0274
1.23 - 1.15     195    195    100.0     4.61      74.9   27.82  0.0448  0.0315
1.15 - 1.10     182    182    100.0     4.62      51.9   22.41  0.0554  0.0353
1.10 - 1.04     217    217    100.0     4.61      48.0   20.66  0.0536  0.0408
1.04 - 1.01     152    152    100.0     4.20      40.5   17.78  0.0611  0.0469
1.01 - 0.97     199    199    100.0     3.90      30.5   15.42  0.0666  0.0539
0.97 - 0.94     192    192    100.0     3.62      25.9   13.40  0.0722  0.0639
0.94 - 0.91     212    212    100.0     3.40      27.1   12.39  0.0719  0.0669
0.91 - 0.89     147    147    100.0     3.23      20.5    9.75  0.0830  0.0834
0.89 - 0.86     272    272    100.0     2.80      17.4    8.00  0.1068  0.1025
0.86 - 0.84     190    190    100.0     2.65      19.8    7.92  0.0934  0.1053
0.84 - 0.82     216    217     99.5     2.31      17.0    6.35  0.1073  0.1285
0.82 - 0.81     117    118     99.2     2.15      15.0    5.67  0.1140  0.1539
0.81 - 0.79     247    249     99.2     2.15      14.2    5.22  0.1191  0.1625
0.79 - 0.78     119    119    100.0     2.12      13.7    5.09  0.1278  0.1778
0.78 - 0.77     153    154     99.4     2.03      13.6    4.71  0.1505  0.1883
#--------------------------------------------------------------------------------
0.87 - 0.77    1133   1138     99.6     2.28      15.9    6.02  0.1122  0.1421
 Inf - 0.77    3749   3760     99.7     3.59      56.9   18.12  0.0435  0.0419
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_abs_structure_details 
;
Flack x determined using 2254 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

The H atoms of the NH2 group could not readily be refined, so they were
placed in-plane and allowed to ride. This is an approximation.
;
_refine_ls_number_reflns         6380
_refine_ls_number_parameters     388
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.050

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.70935(5) 0.93063(5) 0.70001(6) 0.02140(19) Uani 1 1 d . . . . .
S12 S 0.75561(6) 0.78116(5) 0.88500(7) 0.0285(2) Uani 1 1 d . . . . .
O11 O 0.71454(15) 0.98047(15) 0.6077(2) 0.0287(6) Uani 1 1 d . . . . .
O12 O 0.76890(15) 0.94912(15) 0.8124(2) 0.0270(5) Uani 1 1 d . . . . .
N11 N 0.3553(2) 0.9487(2) 0.7018(3) 0.0425(9) Uani 1 1 d . . . . .
H10 H 0.345762 0.944066 0.765783 0.064 Uiso 1 1 calc R U . . .
H11 H 0.311870 0.954469 0.637564 0.064 Uiso 1 1 calc R U . . .
N12 N 0.72107(17) 0.83631(17) 0.6651(2) 0.0210(6) Uani 1 1 d . . . . .
N13 N 0.73906(17) 0.69598(18) 0.7109(2) 0.0238(6) Uani 1 1 d . . . . .
H17 H 0.730468 0.681289 0.640655 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4377(2) 0.9468(2) 0.7022(3) 0.0264(7) Uani 1 1 d . . . . .
C12 C 0.4536(2) 0.9536(2) 0.6008(3) 0.0278(8) Uani 1 1 d . . . . .
H12 H 0.406942 0.961364 0.531520 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5365(2) 0.9489(2) 0.6008(3) 0.0262(7) Uani 1 1 d . . . . .
H13 H 0.546801 0.952391 0.531535 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6054(2) 0.93908(19) 0.7028(3) 0.0215(7) Uani 1 1 d . . . . .
C15 C 0.5903(2) 0.93396(19) 0.8048(3) 0.0240(7) Uani 1 1 d . . . . .
H15 H 0.637027 0.927975 0.874400 0.029 Uiso 1 1 calc R U . . .
C16 C 0.5071(2) 0.9377(2) 0.8031(3) 0.0266(7) Uani 1 1 d . . . . .
H16 H 0.496775 0.933980 0.872275 0.032 Uiso 1 1 calc R U . . .
C17 C 0.7368(2) 0.7757(2) 0.7417(3) 0.0199(7) Uani 1 1 d . . . . .
C18 C 0.7559(2) 0.6389(2) 0.7977(3) 0.0273(8) Uani 1 1 d . . . . .
H18 H 0.760044 0.580701 0.787929 0.033 Uiso 1 1 calc R U . . .
C19 C 0.7655(2) 0.6740(2) 0.8953(3) 0.0300(8) Uani 1 1 d . . . . .
H19 H 0.776556 0.644058 0.963842 0.036 Uiso 1 1 calc R U . . .
S21 S 0.70903(5) 0.57221(5) 0.43003(6) 0.02053(18) Uani 1 1 d . . . . .
S22 S 0.71812(6) 0.72533(5) 0.27225(7) 0.0276(2) Uani 1 1 d . . . . .
O21 O 0.70526(15) 0.52094(14) 0.52259(19) 0.0271(6) Uani 1 1 d . . . . .
O22 O 0.77801(14) 0.55459(15) 0.38822(19) 0.0256(5) Uani 1 1 d . . . . .
N21 N 0.37843(19) 0.5184(2) 0.0551(3) 0.0370(8) Uani 1 1 d . . . . .
H20 H 0.329893 0.524107 0.067644 0.055 Uiso 1 1 calc R U . . .
H21 H 0.377539 0.503554 -0.012385 0.055 Uiso 1 1 calc R U . . .
N22 N 0.71378(17) 0.66595(18) 0.4767(2) 0.0218(6) Uani 1 1 d . . . . .
N23 N 0.71580(17) 0.80809(17) 0.4410(2) 0.0238(6) Uani 1 1 d . . . . .
H27 H 0.715965 0.821753 0.508590 0.036 Uiso 1 1 calc R U . . .
C21 C 0.4550(2) 0.5326(2) 0.1401(3) 0.0259(7) Uani 1 1 d . . . . .
C22 C 0.4572(2) 0.5563(2) 0.2479(3) 0.0264(8) Uani 1 1 d . . . . .
H22 H 0.404813 0.562879 0.261452 0.032 Uiso 1 1 calc R U . . .
C23 C 0.5347(2) 0.5703(2) 0.3346(3) 0.0234(7) Uani 1 1 d . . . . .
H23 H 0.535163 0.586695 0.407081 0.028 Uiso 1 1 calc R U . . .
C24 C 0.6120(2) 0.56054(19) 0.3162(3) 0.0204(7) Uani 1 1 d . . . . .
C25 C 0.6103(2) 0.5393(2) 0.2079(3) 0.0231(7) Uani 1 1 d . . . . .
H25 H 0.662707 0.534498 0.194018 0.028 Uiso 1 1 calc R U . . .
C26 C 0.5337(2) 0.5255(2) 0.1220(3) 0.0250(7) Uani 1 1 d . . . . .
H26 H 0.533501 0.510908 0.048999 0.030 Uiso 1 1 calc R U . . .
C27 C 0.7169(2) 0.7285(2) 0.4085(3) 0.0211(7) Uani 1 1 d . . . . .
C28 C 0.7144(2) 0.8666(2) 0.3605(3) 0.0264(8) Uani 1 1 d . . . . .
H28 H 0.713474 0.924846 0.372462 0.032 Uiso 1 1 calc R U . . .
C29 C 0.7144(2) 0.8329(2) 0.2644(3) 0.0279(7) Uani 1 1 d . . . . .
H29 H 0.712694 0.863898 0.199610 0.033 Uiso 1 1 calc R U . . .
O30 O 0.65670(18) 0.7381(2) 1.0403(2) 0.0491(8) Uani 1 1 d . . . . .
N30 N 0.5140(2) 0.7123(2) 0.9446(3) 0.0363(8) Uani 1 1 d . . . . .
C30 C 0.5984(3) 0.6959(3) 0.9751(3) 0.0423(10) Uani 1 1 d . . . . .
H30 H 0.614386 0.647732 0.943709 0.051 Uiso 1 1 calc R U . . .
C31 C 0.4519(3) 0.6620(3) 0.8587(4) 0.0414(10) Uani 1 1 d . . . . .
H31A H 0.397767 0.659906 0.874618 0.050 Uiso 1 1 calc R U . . .
H31B H 0.474246 0.604535 0.863319 0.050 Uiso 1 1 calc R U . . .
C32 C 0.4324(3) 0.6945(3) 0.7391(3) 0.0379(9) Uani 1 1 d . . . . .
H32A H 0.408206 0.751184 0.733724 0.045 Uiso 1 1 calc R U . . .
H32B H 0.388094 0.658586 0.685622 0.045 Uiso 1 1 calc R U . . .
C33 C 0.5109(2) 0.6971(3) 0.7034(3) 0.0372(9) Uani 1 1 d . . . . .
H33A H 0.550945 0.740371 0.748222 0.045 Uiso 1 1 calc R U . . .
H33B H 0.541003 0.643000 0.721323 0.045 Uiso 1 1 calc R U . . .
C34 C 0.4890(3) 0.7155(3) 0.5782(4) 0.0433(10) Uani 1 1 d . . . . .
H34A H 0.541890 0.716363 0.560628 0.065 Uiso 1 1 calc R U . . .
H34B H 0.450454 0.672191 0.533135 0.065 Uiso 1 1 calc R U . . .
H34C H 0.460403 0.769640 0.560055 0.065 Uiso 1 1 calc R U . . .
C35 C 0.4861(3) 0.7803(2) 0.9981(4) 0.0383(9) Uani 1 1 d . . . . .
H35A H 0.431037 0.802314 0.944814 0.046 Uiso 1 1 calc R U . . .
H35B H 0.529194 0.825462 1.014516 0.046 Uiso 1 1 calc R U . . .
C36 C 0.4739(2) 0.7548(2) 1.1075(3) 0.0339(9) Uani 1 1 d . . . . .
H36A H 0.423648 0.717191 1.089280 0.041 Uiso 1 1 calc R U . . .
H36B H 0.525212 0.723563 1.155102 0.041 Uiso 1 1 calc R U . . .
C37 C 0.4600(3) 0.8285(3) 1.1748(3) 0.0386(9) Uani 1 1 d . . . . .
H37A H 0.402999 0.853383 1.133452 0.046 Uiso 1 1 calc R U . . .
H37B H 0.504253 0.871186 1.180502 0.046 Uiso 1 1 calc R U . . .
C38 C 0.4645(3) 0.8046(3) 1.2937(4) 0.0465(11) Uani 1 1 d . . . . .
H38A H 0.455189 0.854075 1.333160 0.070 Uiso 1 1 calc R U . . .
H38B H 0.419972 0.763244 1.288683 0.070 Uiso 1 1 calc R U . . .
H38C H 0.521261 0.781053 1.335750 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.443(2) . ?
S11 O12 1.446(3) . ?
S11 N12 1.611(3) . ?
S11 C14 1.745(3) . ?
S12 C17 1.726(3) . ?
S12 C19 1.732(4) . ?
N11 C11 1.368(4) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.333(4) . ?
N13 C17 1.344(4) . ?
N13 C18 1.381(5) . ?
N13 H17 0.8800 . ?
C11 C16 1.391(5) . ?
C11 C12 1.400(5) . ?
C12 C13 1.381(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(5) . ?
C15 C16 1.378(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.314(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S21 O22 1.449(2) . ?
S21 O21 1.450(2) . ?
S21 N22 1.611(3) . ?
S21 C24 1.751(3) . ?
S22 C27 1.729(3) . ?
S22 C29 1.734(4) . ?
N21 C21 1.363(4) . ?
N21 H20 0.8800 . ?
N21 H21 0.8800 . ?
N22 C27 1.337(4) . ?
N23 C27 1.347(4) . ?
N23 C28 1.380(4) . ?
N23 H27 0.8800 . ?
C21 C22 1.402(5) . ?
C21 C26 1.410(4) . ?
C22 C23 1.383(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.401(4) . ?
C25 C26 1.368(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C28 C29 1.329(5) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
O30 C30 1.232(5) . ?
N30 C30 1.342(5) . ?
N30 C35 1.446(5) . ?
N30 C31 1.451(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.521(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.523(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.522(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.522(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.522(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.527(6) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.64(15) . . ?
O11 S11 N12 104.76(14) . . ?
O12 S11 N12 110.82(14) . . ?
O11 S11 C14 108.36(15) . . ?
O12 S11 C14 107.64(15) . . ?
N12 S11 C14 107.16(14) . . ?
C17 S12 C19 90.31(17) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 120.1(2) . . ?
C17 N13 C18 115.0(3) . . ?
C17 N13 H17 122.5 . . ?
C18 N13 H17 122.5 . . ?
N11 C11 C16 120.7(3) . . ?
N11 C11 C12 120.4(3) . . ?
C16 C11 C12 118.9(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 S11 119.0(3) . . ?
C15 C14 S11 120.9(3) . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
N12 C17 N13 120.4(3) . . ?
N12 C17 S12 129.8(3) . . ?
N13 C17 S12 109.8(2) . . ?
C19 C18 N13 112.5(3) . . ?
C19 C18 H18 123.8 . . ?
N13 C18 H18 123.8 . . ?
C18 C19 S12 112.4(3) . . ?
C18 C19 H19 123.8 . . ?
S12 C19 H19 123.8 . . ?
O22 S21 O21 116.58(14) . . ?
O22 S21 N22 111.93(14) . . ?
O21 S21 N22 104.38(14) . . ?
O22 S21 C24 107.31(15) . . ?
O21 S21 C24 108.14(15) . . ?
N22 S21 C24 108.21(15) . . ?
C27 S22 C29 90.86(16) . . ?
C21 N21 H20 120.0 . . ?
C21 N21 H21 120.0 . . ?
H20 N21 H21 120.0 . . ?
C27 N22 S21 118.5(2) . . ?
C27 N23 C28 115.0(3) . . ?
C27 N23 H27 122.5 . . ?
C28 N23 H27 122.5 . . ?
N21 C21 C22 120.5(3) . . ?
N21 C21 C26 121.3(3) . . ?
C22 C21 C26 118.2(3) . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C25 119.3(3) . . ?
C23 C24 S21 119.2(2) . . ?
C25 C24 S21 121.5(2) . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 121.0(3) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
N22 C27 N23 120.7(3) . . ?
N22 C27 S22 129.5(3) . . ?
N23 C27 S22 109.7(2) . . ?
C29 C28 N23 112.9(3) . . ?
C29 C28 H28 123.5 . . ?
N23 C28 H28 123.5 . . ?
C28 C29 S22 111.5(3) . . ?
C28 C29 H29 124.3 . . ?
S22 C29 H29 124.3 . . ?
C30 N30 C35 119.3(4) . . ?
C30 N30 C31 120.0(3) . . ?
C35 N30 C31 120.7(3) . . ?
O30 C30 N30 125.4(4) . . ?
O30 C30 H30 117.3 . . ?
N30 C30 H30 117.3 . . ?
N30 C31 C32 113.4(3) . . ?
N30 C31 H31A 108.9 . . ?
C32 C31 H31A 108.9 . . ?
N30 C31 H31B 108.9 . . ?
C32 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C31 C32 C33 113.5(3) . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C34 C33 C32 113.4(3) . . ?
C34 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N30 C35 C36 112.9(3) . . ?
N30 C35 H35A 109.0 . . ?
C36 C35 H35A 109.0 . . ?
N30 C35 H35B 109.0 . . ?
C36 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C37 C36 C35 113.1(3) . . ?
C37 C36 H36A 109.0 . . ?
C35 C36 H36A 109.0 . . ?
C37 C36 H36B 109.0 . . ?
C35 C36 H36B 109.0 . . ?
H36A C36 H36B 107.8 . . ?
C36 C37 C38 112.8(3) . . ?
C36 C37 H37A 109.0 . . ?
C38 C37 H37A 109.0 . . ?
C36 C37 H37B 109.0 . . ?
C38 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 166.5(3) . . . . ?
O12 S11 N12 C17 38.6(3) . . . . ?
C14 S11 N12 C17 -78.5(3) . . . . ?
N11 C11 C12 C13 -177.8(3) . . . . ?
C16 C11 C12 C13 1.7(5) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C12 C13 C14 S11 178.3(3) . . . . ?
O11 S11 C14 C13 32.9(3) . . . . ?
O12 S11 C14 C13 161.1(3) . . . . ?
N12 S11 C14 C13 -79.7(3) . . . . ?
O11 S11 C14 C15 -148.8(3) . . . . ?
O12 S11 C14 C15 -20.6(3) . . . . ?
N12 S11 C14 C15 98.6(3) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
S11 C14 C15 C16 -177.5(2) . . . . ?
C14 C15 C16 C11 -0.3(5) . . . . ?
N11 C11 C16 C15 178.6(3) . . . . ?
C12 C11 C16 C15 -1.0(5) . . . . ?
S11 N12 C17 N13 174.1(2) . . . . ?
S11 N12 C17 S12 -5.4(4) . . . . ?
C18 N13 C17 N12 -180.0(3) . . . . ?
C18 N13 C17 S12 -0.4(3) . . . . ?
C19 S12 C17 N12 179.4(3) . . . . ?
C19 S12 C17 N13 -0.1(3) . . . . ?
C17 N13 C18 C19 0.9(4) . . . . ?
N13 C18 C19 S12 -0.9(4) . . . . ?
C17 S12 C19 C18 0.6(3) . . . . ?
O22 S21 N22 C27 53.8(3) . . . . ?
O21 S21 N22 C27 -179.2(2) . . . . ?
C24 S21 N22 C27 -64.2(3) . . . . ?
N21 C21 C22 C23 179.6(3) . . . . ?
C26 C21 C22 C23 -1.6(5) . . . . ?
C21 C22 C23 C24 -0.4(5) . . . . ?
C22 C23 C24 C25 2.3(5) . . . . ?
C22 C23 C24 S21 -175.9(3) . . . . ?
O22 S21 C24 C23 177.1(2) . . . . ?
O21 S21 C24 C23 50.6(3) . . . . ?
N22 S21 C24 C23 -61.9(3) . . . . ?
O22 S21 C24 C25 -1.1(3) . . . . ?
O21 S21 C24 C25 -127.6(3) . . . . ?
N22 S21 C24 C25 119.9(3) . . . . ?
C23 C24 C25 C26 -2.3(5) . . . . ?
S21 C24 C25 C26 175.9(3) . . . . ?
C24 C25 C26 C21 0.3(5) . . . . ?
N21 C21 C26 C25 -179.5(3) . . . . ?
C22 C21 C26 C25 1.6(5) . . . . ?
S21 N22 C27 N23 176.1(2) . . . . ?
S21 N22 C27 S22 -1.0(4) . . . . ?
C28 N23 C27 N22 -176.5(3) . . . . ?
C28 N23 C27 S22 1.1(3) . . . . ?
C29 S22 C27 N22 175.9(3) . . . . ?
C29 S22 C27 N23 -1.4(2) . . . . ?
C27 N23 C28 C29 0.0(4) . . . . ?
N23 C28 C29 S22 -1.0(4) . . . . ?
C27 S22 C29 C28 1.4(3) . . . . ?
C35 N30 C30 O30 -5.8(6) . . . . ?
C31 N30 C30 O30 174.1(4) . . . . ?
C30 N30 C31 C32 -89.2(5) . . . . ?
C35 N30 C31 C32 90.7(4) . . . . ?
N30 C31 C32 C33 60.9(5) . . . . ?
C31 C32 C33 C34 170.2(4) . . . . ?
C30 N30 C35 C36 -87.0(4) . . . . ?
C31 N30 C35 C36 93.2(4) . . . . ?
N30 C35 C36 C37 169.8(3) . . . . ?
C35 C36 C37 C38 -169.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O22 0.88 2.21 3.055(4) 160.6 4_465 yes
N11 H11 O21 0.88 2.14 2.950(4) 153.1 3_455 yes
N13 H17 N22 0.88 2.01 2.879(4) 171.3 . yes
N21 H20 O11 0.88 2.15 3.022(4) 171.5 4_464 yes
N21 H21 O12 0.88 2.47 3.163(4) 136.1 3_444 yes
N23 H27 N12 0.88 1.96 2.837(4) 172.1 . yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9
_database_code_depnum_ccdc_archive 'CCDC 2120775'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 10o
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, hexahydro-2H-azepin-2-one (1:2) solvate'
_chemical_name_common            'Sulfathiazole, caprolactam solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, 2(C6 H11 N O)'
_chemical_formula_sum            'C21 H31 N5 O4 S2'
_chemical_formula_weight         481.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.448(2)
_cell_length_b                   14.224(3)
_cell_length_c                   15.323(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.60(3)
_cell_angle_gamma                90
_cell_volume                     2319.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13166
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      30.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13166
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.126
_diffrn_reflns_theta_max         30.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             6771
_reflns_number_gt                5134
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  10o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 2.84     108    124     87.1     1.56     380.3   49.08  0.0092  0.0174
2.84 - 1.94     244    245     99.6     1.86     239.6   39.58  0.0115  0.0207
1.94 - 1.54     355    355    100.0     1.88     150.5   33.20  0.0141  0.0232
1.54 - 1.35     344    344    100.0     1.90     104.6   29.08  0.0172  0.0252
1.35 - 1.22     363    363    100.0     1.90      88.3   25.57  0.0193  0.0276
1.22 - 1.13     360    360    100.0     1.92      81.1   23.32  0.0196  0.0286
1.13 - 1.06     368    368    100.0     1.91      59.8   20.53  0.0242  0.0344
1.06 - 1.01     329    329    100.0     1.90      44.2   16.89  0.0319  0.0405
1.01 - 0.96     395    395    100.0     1.92      34.5   14.70  0.0396  0.0474
0.96 - 0.93     301    303     99.3     1.89      34.7   13.36  0.0444  0.0527
0.93 - 0.89     417    426     97.9     1.89      26.4   11.89  0.0573  0.0622
0.89 - 0.86     381    389     97.9     1.88      22.2   10.12  0.0649  0.0736
0.86 - 0.84     265    283     93.6     1.80      19.3    9.08  0.0796  0.0832
0.84 - 0.81     470    490     95.9     1.84      19.9    8.93  0.0762  0.0878
0.81 - 0.79     338    374     90.4     1.74      17.8    8.03  0.0962  0.1019
0.79 - 0.77     364    386     94.3     1.83      16.3    7.31  0.1142  0.1123
0.77 - 0.76     204    234     87.2     1.68      14.4    6.28  0.1314  0.1294
0.76 - 0.74     435    484     89.9     1.74      14.2    5.83  0.1285  0.1355
0.74 - 0.72     437    509     85.9     1.68      13.8    5.93  0.1534  0.1422
0.72 - 0.71     251    286     87.8     1.68       9.1    4.10  0.2266  0.2253
0.71 - 0.70     268    304     88.2     1.67       9.6    3.88  0.2199  0.2233
#--------------------------------------------------------------------------------
0.80 - 0.70    2137   2399     89.1     1.72      13.6    5.86  0.1444  0.1430
 Inf - 0.70    6997   7351     95.2     1.82      53.8   15.24  0.0343  0.0407
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+2.8897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6771
_refine_ls_number_parameters     296
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.077

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.53964(5) 0.52887(3) 0.80100(4) 0.01992(12) Uani 1 1 d . . . . .
S12 S 0.81716(5) 0.50614(5) 0.97116(4) 0.03118(15) Uani 1 1 d . . . . .
O11 O 0.40745(15) 0.51595(12) 0.74855(11) 0.0290(4) Uani 1 1 d . . . . .
O12 O 0.62713(17) 0.47314(11) 0.77431(12) 0.0291(4) Uani 1 1 d . . . . .
N11 N 0.6605(2) 0.93114(14) 0.78614(18) 0.0356(5) Uani 1 1 d D . . . .
H10 H 0.724(3) 0.9539(19) 0.772(2) 0.053 Uiso 1 1 d D U . . .
H11 H 0.607(3) 0.9766(18) 0.788(2) 0.053 Uiso 1 1 d D U . . .
N12 N 0.55590(16) 0.50785(12) 0.90863(12) 0.0198(3) Uani 1 1 d . . . . .
N13 N 0.67876(16) 0.48815(12) 1.06557(13) 0.0208(3) Uani 1 1 d . . . . .
H17 H 0.612741 0.483230 1.081682 0.031 Uiso 1 1 calc R U . . .
C11 C 0.63220(19) 0.83844(15) 0.78812(15) 0.0218(4) Uani 1 1 d . . . . .
C12 C 0.5206(2) 0.80993(15) 0.79933(15) 0.0232(4) Uani 1 1 d . . . . .
H12 H 0.463455 0.856087 0.804334 0.028 Uiso 1 1 calc R U . . .
C13 C 0.49346(19) 0.71608(15) 0.80313(15) 0.0218(4) Uani 1 1 d . . . . .
H13 H 0.418036 0.697857 0.810895 0.026 Uiso 1 1 calc R U . . .
C14 C 0.57711(18) 0.64734(14) 0.79555(14) 0.0181(4) Uani 1 1 d . . . . .
C15 C 0.68812(19) 0.67422(14) 0.78481(14) 0.0200(4) Uani 1 1 d . . . . .
H15 H 0.745556 0.627747 0.780834 0.024 Uiso 1 1 calc R U . . .
C16 C 0.71483(19) 0.76874(15) 0.77992(15) 0.0219(4) Uani 1 1 d . . . . .
H16 H 0.789590 0.786604 0.770957 0.026 Uiso 1 1 calc R U . . .
C17 C 0.66801(18) 0.50047(14) 0.97631(15) 0.0187(4) Uani 1 1 d . . . . .
C18 C 0.7997(2) 0.48368(17) 1.13062(16) 0.0269(5) Uani 1 1 d . . . . .
H18 H 0.819356 0.474799 1.195931 0.032 Uiso 1 1 calc R U . . .
C19 C 0.8863(2) 0.4931(2) 1.09217(18) 0.0340(5) Uani 1 1 d . . . . .
H19 H 0.974403 0.492779 1.126484 0.041 Uiso 1 1 calc R U . . .
O30 O 0.55349(17) 0.11757(13) 0.79310(12) 0.0338(4) Uani 1 1 d . . . . .
N30 N 0.46215(16) 0.08665(12) 0.89170(13) 0.0213(3) Uani 1 1 d . . . . .
H30 H 0.452220 0.027808 0.872639 0.026 Uiso 1 1 calc R U . . .
C30 C 0.51007(19) 0.14890(16) 0.84922(16) 0.0248(4) Uani 1 1 d . . . . .
C31 C 0.5027(2) 0.25201(16) 0.86763(16) 0.0261(4) Uani 1 1 d . . . . .
H31A H 0.544249 0.287779 0.831736 0.031 Uiso 1 1 calc R U . . .
H31B H 0.549134 0.264498 0.935169 0.031 Uiso 1 1 calc R U . . .
C32 C 0.3665(2) 0.28730(16) 0.84024(16) 0.0270(5) Uani 1 1 d . . . . .
H32A H 0.363860 0.355384 0.826244 0.032 Uiso 1 1 calc R U . . .
H32B H 0.312705 0.254705 0.782270 0.032 Uiso 1 1 calc R U . . .
C33 C 0.3125(2) 0.27120(16) 0.91663(17) 0.0275(5) Uani 1 1 d . . . . .
H33A H 0.366571 0.303574 0.974636 0.033 Uiso 1 1 calc R U . . .
H33B H 0.227985 0.300061 0.896443 0.033 Uiso 1 1 calc R U . . .
C34 C 0.3022(2) 0.16796(16) 0.93884(18) 0.0278(5) Uani 1 1 d . . . . .
H34A H 0.267724 0.163535 0.989237 0.033 Uiso 1 1 calc R U . . .
H34B H 0.241873 0.136904 0.882390 0.033 Uiso 1 1 calc R U . . .
C35 C 0.4260(2) 0.11525(17) 0.96954(18) 0.0306(5) Uani 1 1 d . . . . .
H35A H 0.492846 0.155807 1.012439 0.037 Uiso 1 1 calc R U . . .
H35B H 0.419679 0.058598 1.005072 0.037 Uiso 1 1 calc R U . . .
O40 O 0.28574(18) 0.74103(16) 0.90400(13) 0.0444(5) Uani 1 1 d . . . . .
N40 N 0.25568(15) 0.87210(13) 0.96695(12) 0.0202(3) Uani 1 1 d . . . . .
H40 H 0.336626 0.884277 0.986263 0.024 Uiso 1 1 calc R U . . .
C40 C 0.2113(2) 0.79275(19) 0.91906(16) 0.0292(5) Uani 1 1 d . . . . .
C41 C 0.0740(2) 0.77038(19) 0.88933(17) 0.0321(5) Uani 1 1 d . . . . .
H41A H 0.054267 0.715403 0.846721 0.039 Uiso 1 1 calc R U . . .
H41B H 0.024412 0.824397 0.853930 0.039 Uiso 1 1 calc R U . . .
C42 C 0.0347(2) 0.74881(18) 0.97311(19) 0.0332(5) Uani 1 1 d . . . . .
H42A H -0.042241 0.709676 0.950964 0.040 Uiso 1 1 calc R U . . .
H42B H 0.101879 0.711600 1.019892 0.040 Uiso 1 1 calc R U . . .
C43 C 0.0097(2) 0.83571(17) 1.02062(18) 0.0294(5) Uani 1 1 d . . . . .
H43A H -0.016147 0.815981 1.072817 0.035 Uiso 1 1 calc R U . . .
H43B H -0.061208 0.870826 0.974912 0.035 Uiso 1 1 calc R U . . .
C44 C 0.1224(2) 0.90122(17) 1.05916(16) 0.0273(4) Uani 1 1 d . . . . .
H44A H 0.098297 0.955482 1.089381 0.033 Uiso 1 1 calc R U . . .
H44B H 0.190685 0.867321 1.108486 0.033 Uiso 1 1 calc R U . . .
C45 C 0.1732(2) 0.93814(17) 0.98755(18) 0.0293(5) Uani 1 1 d . . . . .
H45A H 0.101935 0.953006 0.928790 0.035 Uiso 1 1 calc R U . . .
H45B H 0.219733 0.997223 1.011375 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.4403(17) . ?
S11 O12 1.4493(16) . ?
S11 N12 1.6180(18) . ?
S11 C14 1.748(2) . ?
S12 C19 1.737(3) . ?
S12 C17 1.740(2) . ?
N11 C11 1.361(3) . ?
N11 H10 0.89(2) . ?
N11 H11 0.89(2) . ?
N12 C17 1.324(3) . ?
N13 C17 1.339(3) . ?
N13 C18 1.378(3) . ?
N13 H17 0.8800 . ?
C11 C16 1.407(3) . ?
C11 C12 1.409(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.403(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.333(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C30 1.225(3) . ?
N30 C30 1.331(3) . ?
N30 C35 1.457(3) . ?
N30 H30 0.8800 . ?
C30 C31 1.502(3) . ?
C31 C32 1.542(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.529(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.522(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.517(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
O40 C40 1.211(3) . ?
N40 C40 1.340(3) . ?
N40 C45 1.447(3) . ?
N40 H40 0.8800 . ?
C40 C41 1.501(3) . ?
C41 C42 1.540(4) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.514(3) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.523(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.513(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.78(11) . . ?
O11 S11 N12 104.37(10) . . ?
O12 S11 N12 110.76(10) . . ?
O11 S11 C14 108.80(10) . . ?
O12 S11 C14 107.84(10) . . ?
N12 S11 C14 106.77(9) . . ?
C19 S12 C17 90.92(11) . . ?
C11 N11 H10 125.3(18) . . ?
C11 N11 H11 122.0(18) . . ?
H10 N11 H11 111.6(15) . . ?
C17 N12 S11 121.84(15) . . ?
C17 N13 C18 115.78(18) . . ?
C17 N13 H17 122.1 . . ?
C18 N13 H17 122.1 . . ?
N11 C11 C16 120.47(19) . . ?
N11 C11 C12 121.0(2) . . ?
C16 C11 C12 118.50(19) . . ?
C13 C12 C11 120.87(19) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.02(19) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.90(18) . . ?
C15 C14 S11 121.37(15) . . ?
C13 C14 S11 118.73(15) . . ?
C16 C15 C14 120.07(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.61(18) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N12 C17 N13 120.56(18) . . ?
N12 C17 S12 130.18(16) . . ?
N13 C17 S12 109.25(15) . . ?
C19 C18 N13 112.9(2) . . ?
C19 C18 H18 123.6 . . ?
N13 C18 H18 123.6 . . ?
C18 C19 S12 111.18(18) . . ?
C18 C19 H19 124.4 . . ?
S12 C19 H19 124.4 . . ?
C30 N30 C35 120.47(18) . . ?
C30 N30 H30 119.8 . . ?
C35 N30 H30 119.8 . . ?
O30 C30 N30 116.6(2) . . ?
O30 C30 C31 123.5(2) . . ?
N30 C30 C31 119.74(19) . . ?
C30 C31 C32 112.82(18) . . ?
C30 C31 H31A 109.0 . . ?
C32 C31 H31A 109.0 . . ?
C30 C31 H31B 109.0 . . ?
C32 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C33 C32 C31 113.33(19) . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C31 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C34 C33 C32 113.73(19) . . ?
C34 C33 H33A 108.8 . . ?
C32 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C32 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C35 C34 C33 113.92(19) . . ?
C35 C34 H34A 108.8 . . ?
C33 C34 H34A 108.8 . . ?
C35 C34 H34B 108.8 . . ?
C33 C34 H34B 108.8 . . ?
H34A C34 H34B 107.7 . . ?
N30 C35 C34 113.5(2) . . ?
N30 C35 H35A 108.9 . . ?
C34 C35 H35A 108.9 . . ?
N30 C35 H35B 108.9 . . ?
C34 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?
C40 N40 C45 121.32(18) . . ?
C40 N40 H40 119.3 . . ?
C45 N40 H40 119.3 . . ?
O40 C40 N40 117.7(2) . . ?
O40 C40 C41 123.1(2) . . ?
N40 C40 C41 119.2(2) . . ?
C40 C41 C42 112.6(2) . . ?
C40 C41 H41A 109.1 . . ?
C42 C41 H41A 109.1 . . ?
C40 C41 H41B 109.1 . . ?
C42 C41 H41B 109.1 . . ?
H41A C41 H41B 107.8 . . ?
C43 C42 C41 113.8(2) . . ?
C43 C42 H42A 108.8 . . ?
C41 C42 H42A 108.8 . . ?
C43 C42 H42B 108.8 . . ?
C41 C42 H42B 108.8 . . ?
H42A C42 H42B 107.7 . . ?
C42 C43 C44 113.76(19) . . ?
C42 C43 H43A 108.8 . . ?
C44 C43 H43A 108.8 . . ?
C42 C43 H43B 108.8 . . ?
C44 C43 H43B 108.8 . . ?
H43A C43 H43B 107.7 . . ?
C45 C44 C43 115.3(2) . . ?
C45 C44 H44A 108.4 . . ?
C43 C44 H44A 108.4 . . ?
C45 C44 H44B 108.4 . . ?
C43 C44 H44B 108.4 . . ?
H44A C44 H44B 107.5 . . ?
N40 C45 C44 112.89(19) . . ?
N40 C45 H45A 109.0 . . ?
C44 C45 H45A 109.0 . . ?
N40 C45 H45B 109.0 . . ?
C44 C45 H45B 109.0 . . ?
H45A C45 H45B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 170.75(17) . . . . ?
O12 S11 N12 C17 43.0(2) . . . . ?
C14 S11 N12 C17 -74.12(18) . . . . ?
N11 C11 C12 C13 -178.7(2) . . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C12 C13 C14 S11 179.83(17) . . . . ?
O11 S11 C14 C15 -139.85(17) . . . . ?
O12 S11 C14 C15 -11.0(2) . . . . ?
N12 S11 C14 C15 108.03(18) . . . . ?
O11 S11 C14 C13 40.76(19) . . . . ?
O12 S11 C14 C13 169.57(17) . . . . ?
N12 S11 C14 C13 -71.35(18) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
S11 C14 C15 C16 179.46(16) . . . . ?
C14 C15 C16 C11 1.6(3) . . . . ?
N11 C11 C16 C15 178.0(2) . . . . ?
C12 C11 C16 C15 -1.4(3) . . . . ?
S11 N12 C17 N13 176.34(15) . . . . ?
S11 N12 C17 S12 -2.4(3) . . . . ?
C18 N13 C17 N12 -178.46(19) . . . . ?
C18 N13 C17 S12 0.5(2) . . . . ?
C19 S12 C17 N12 177.9(2) . . . . ?
C19 S12 C17 N13 -0.87(17) . . . . ?
C17 N13 C18 C19 0.3(3) . . . . ?
N13 C18 C19 S12 -1.0(3) . . . . ?
C17 S12 C19 C18 1.1(2) . . . . ?
C35 N30 C30 O30 170.6(2) . . . . ?
C35 N30 C30 C31 -12.6(3) . . . . ?
O30 C30 C31 C32 116.6(2) . . . . ?
N30 C30 C31 C32 -60.0(3) . . . . ?
C30 C31 C32 C33 83.9(2) . . . . ?
C31 C32 C33 C34 -63.1(3) . . . . ?
C32 C33 C34 C35 57.8(3) . . . . ?
C30 N30 C35 C34 77.1(3) . . . . ?
C33 C34 C35 N30 -80.1(3) . . . . ?
C45 N40 C40 O40 179.6(2) . . . . ?
C45 N40 C40 C41 -2.3(3) . . . . ?
O40 C40 C41 C42 110.5(3) . . . . ?
N40 C40 C41 C42 -67.5(3) . . . . ?
C40 C41 C42 C43 82.4(3) . . . . ?
C41 C42 C43 C44 -59.4(3) . . . . ?
C42 C43 C44 C45 58.8(3) . . . . ?
C40 N40 C45 C44 70.2(3) . . . . ?
C43 C44 C45 N40 -81.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.89(2) 2.09(2) 2.964(3) 166(3) 2_656 yes
N11 H11 O30 0.89(2) 2.11(2) 2.939(3) 154(2) 1_565 yes
N13 H17 S11 0.88 2.93 3.775(2) 160.4 3_667 yes
N13 H17 N12 0.88 1.99 2.856(2) 166.1 3_667 yes
N40 H40 N30 0.88 2.41 3.212(3) 151.9 3_667 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8_sq
_database_code_depnum_ccdc_archive 'CCDC 2120770'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 9o
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, alpha-Me-gamma-butyrolactone (1:1) solvate'
_chemical_name_common            'Sulfathiazole, alpha-Me-gamma-butyrolactone'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C5 H8 O4'
_chemical_formula_sum            'C14 H17 N3 O4 S2'
_chemical_formula_weight         355.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.392(2)
_cell_length_b                   21.207(4)
_cell_length_c                   9.302(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.12(3)
_cell_angle_gamma                90
_cell_volume                     1653.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5903
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.345
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9723
_diffrn_reflns_av_unetI/netI     0.1000
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.394
_diffrn_reflns_theta_max         24.979
_diffrn_reflns_theta_full        24.979
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2893
_reflns_number_gt                1628
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

Structure factors included contributions from the .fab file.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  9o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.58      45     47     95.7     3.21    1267.0   23.46  0.0194  0.0305
3.58 - 2.33     104    104    100.0     3.61     508.5   22.79  0.0279  0.0325
2.33 - 1.84     152    152    100.0     3.60     230.9   18.64  0.0404  0.0392
1.84 - 1.60     148    148    100.0     3.75     188.3   14.60  0.0479  0.0445
1.60 - 1.45     156    156    100.0     3.76     140.7   12.91  0.0687  0.0540
1.45 - 1.34     150    150    100.0     3.73     116.7   10.25  0.0687  0.0660
1.34 - 1.26     164    164    100.0     3.63      85.7    8.62  0.0922  0.0832
1.26 - 1.20     129    129    100.0     3.71      84.0    8.04  0.0930  0.0865
1.20 - 1.15     147    147    100.0     3.62      94.9    7.28  0.1135  0.0908
1.15 - 1.10     163    163    100.0     3.61      72.4    6.55  0.1204  0.1096
1.10 - 1.06     157    157    100.0     3.70      61.7    6.28  0.1340  0.1225
1.06 - 1.03     129    129    100.0     3.60      41.0    4.45  0.1603  0.1733
1.03 - 1.00     158    158    100.0     3.54      32.2    3.65  0.2289  0.2317
1.00 - 0.97     181    181    100.0     3.65      26.6    3.38  0.2797  0.2671
0.97 - 0.95     111    111    100.0     3.32      19.9    2.71  0.4226  0.3799
0.95 - 0.92     208    208    100.0     3.12      25.5    2.55  0.2941  0.3415
0.92 - 0.90     166    166    100.0     2.67      14.5    1.60  0.3818  0.6786
0.90 - 0.89      84     86     97.7     2.60      19.2    2.00  0.3788  0.5485
0.89 - 0.87     161    162     99.4     2.41      16.2    1.39  0.5154  0.6754
0.87 - 0.85     183    186     98.4     2.18      13.2    1.11  0.5216  0.9275
0.85 - 0.84      94     98     95.9     2.19      12.9    1.12  0.5345  0.8970
#--------------------------------------------------------------------------------
0.94 - 0.84     847    857     98.8     2.53      16.6    1.58  0.4142  0.6407
 Inf - 0.84    2990   3002     99.6     3.31     102.2    7.06  0.0817  0.0913
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;The location of the solvent molecule (alpha-Me-gamma-butyrolactone) is quite
clear, but the electron density comprises an overlay of several orientations
which could not easily be resolved. The most prominent set of peaks in the
electron density could be modelled with restraints to provide a starting set
for energy minimisation. However, acceptable R-factors could only be produced
by applying SQUEEZE. Hence, this CIF has SQUEEZE applied. SQUEEZE identifies
two voids (centred at 0,0,0 and 0.5,0.5,0.5) and corrects for 112 electrons
in each void. The expectation for two solvent molecules per void is 140
electrons. The discrepancy may indicate partial solvent loss from the crystal.,SQUEEZE
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2893
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1554
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.055

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.50909(11) 0.14544(5) 0.38692(8) 0.0399(3) Uani 1 1 d . . . . .
S12 S 0.59372(18) 0.14293(6) 0.73682(11) 0.0822(5) Uani 1 1 d . . . . .
O11 O 0.4962(3) 0.12414(12) 0.2395(2) 0.0509(7) Uani 1 1 d . . . . .
O12 O 0.6410(3) 0.18657(13) 0.4304(3) 0.0533(8) Uani 1 1 d . . . . .
N11 N -0.0928(4) 0.27207(16) 0.5176(3) 0.0559(10) Uani 1 1 d . . . . .
H10 H -0.091661 0.303471 0.579525 0.067 Uiso 1 1 d R U . . .
H11 H -0.183611 0.259601 0.475085 0.067 Uiso 1 1 d R U . . .
N12 N 0.5163(3) 0.08126(13) 0.4789(3) 0.0352(7) Uani 1 1 d . . . . .
N13 N 0.5567(4) 0.02628(15) 0.6905(3) 0.0464(8) Uani 1 1 d . . . . .
H17 H 0.537990 -0.010142 0.647491 0.070 Uiso 1 1 calc R U . . .
C11 C 0.0472(4) 0.24320(19) 0.4881(3) 0.0427(10) Uani 1 1 d . . . . .
C12 C 0.0489(5) 0.19269(18) 0.3900(3) 0.0442(10) Uani 1 1 d . . . . .
H12 H -0.049206 0.178578 0.345356 0.053 Uiso 1 1 calc R U . . .
C13 C 0.1886(4) 0.16301(18) 0.3568(3) 0.0406(10) Uani 1 1 d . . . . .
H13 H 0.187050 0.128894 0.290570 0.049 Uiso 1 1 calc R U . . .
C14 C 0.3333(4) 0.18435(17) 0.4230(3) 0.0362(9) Uani 1 1 d . . . . .
C15 C 0.3339(4) 0.23414(18) 0.5193(3) 0.0397(9) Uani 1 1 d . . . . .
H15 H 0.432243 0.248332 0.563366 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1938(5) 0.26337(18) 0.5520(3) 0.0425(10) Uani 1 1 d . . . . .
H16 H 0.196378 0.297455 0.618329 0.051 Uiso 1 1 calc R U . . .
C17 C 0.5523(4) 0.08086(19) 0.6193(3) 0.0419(9) Uani 1 1 d . . . . .
C18 C 0.5927(7) 0.0311(2) 0.8369(4) 0.0862(17) Uani 1 1 d . . . . .
H18 H 0.602177 -0.004146 0.899853 0.103 Uiso 1 1 calc R U . . .
C19 C 0.6125(8) 0.0899(3) 0.8794(4) 0.113(2) Uani 1 1 d . . . . .
H19 H 0.634459 0.101953 0.976810 0.136 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.442(2) . ?
S11 O12 1.449(3) . ?
S11 N12 1.607(3) . ?
S11 C14 1.739(4) . ?
S12 C17 1.734(4) . ?
S12 C19 1.740(5) . ?
N11 C11 1.366(4) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.324(4) . ?
N13 C17 1.333(5) . ?
N13 C18 1.383(4) . ?
N13 H17 0.8800 . ?
C11 C16 1.403(5) . ?
C11 C12 1.407(5) . ?
C12 C13 1.381(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.406(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(5) . ?
C15 C16 1.378(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.315(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.06(15) . . ?
O11 S11 N12 103.85(15) . . ?
O12 S11 N12 110.82(16) . . ?
O11 S11 C14 108.17(16) . . ?
O12 S11 C14 107.67(17) . . ?
N12 S11 C14 107.87(15) . . ?
C17 S12 C19 89.8(2) . . ?
C11 N11 H10 119.5 . . ?
C11 N11 H11 120.5 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 122.0(3) . . ?
C17 N13 C18 115.1(3) . . ?
C17 N13 H17 122.5 . . ?
C18 N13 H17 122.5 . . ?
N11 C11 C16 121.5(3) . . ?
N11 C11 C12 120.7(3) . . ?
C16 C11 C12 117.8(3) . . ?
C13 C12 C11 122.0(3) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 118.6(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 S11 120.9(3) . . ?
C13 C14 S11 118.9(3) . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N12 C17 N13 119.6(3) . . ?
N12 C17 S12 130.1(3) . . ?
N13 C17 S12 110.3(2) . . ?
C19 C18 N13 112.5(4) . . ?
C19 C18 H18 123.7 . . ?
N13 C18 H18 123.7 . . ?
C18 C19 S12 112.3(3) . . ?
C18 C19 H19 123.9 . . ?
S12 C19 H19 123.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 169.7(3) . . . . ?
O12 S11 N12 C17 42.0(3) . . . . ?
C14 S11 N12 C17 -75.7(3) . . . . ?
N11 C11 C12 C13 179.3(3) . . . . ?
C16 C11 C12 C13 0.4(5) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C12 C13 C14 S11 177.7(3) . . . . ?
O11 S11 C14 C15 -148.0(3) . . . . ?
O12 S11 C14 C15 -19.4(3) . . . . ?
N12 S11 C14 C15 100.3(3) . . . . ?
O11 S11 C14 C13 34.3(3) . . . . ?
O12 S11 C14 C13 162.9(3) . . . . ?
N12 S11 C14 C13 -77.4(3) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
S11 C14 C15 C16 -177.5(3) . . . . ?
C14 C15 C16 C11 0.0(5) . . . . ?
N11 C11 C16 C15 -179.1(3) . . . . ?
C12 C11 C16 C15 -0.2(5) . . . . ?
S11 N12 C17 N13 -180.0(3) . . . . ?
S11 N12 C17 S12 1.7(5) . . . . ?
C18 N13 C17 N12 -178.9(4) . . . . ?
C18 N13 C17 S12 -0.3(4) . . . . ?
C19 S12 C17 N12 177.8(4) . . . . ?
C19 S12 C17 N13 -0.7(4) . . . . ?
C17 N13 C18 C19 1.5(7) . . . . ?
N13 C18 C19 S12 -2.1(7) . . . . ?
C17 S12 C19 C18 1.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.88 2.24 3.082(4) 161.2 4_566 yes
N11 H11 O12 0.88 2.16 2.957(4) 150.0 1_455 yes
N13 H17 S11 0.88 2.91 3.747(3) 159.2 3_656 yes
N13 H17 N12 0.88 1.95 2.820(4) 169.3 3_656 yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_23
_database_code_depnum_ccdc_archive 'CCDC 2120784'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 24o
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (2:1) solvate'
_chemical_name_common            
"Sulfathiazole, N,N'-Dimethylpropylene urea solvate"
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C6 H12 N2 O'
_chemical_formula_sum            'C24 H30 N8 O5 S4'
_chemical_formula_weight         638.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.533(3)
_cell_length_b                   9.996(1)
_cell_length_c                   19.810(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.26(2)
_cell_angle_gamma                90
_cell_volume                     3029.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      74.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    3.295
_shelx_estimated_absorpt_T_min   0.438
_shelx_estimated_absorpt_T_max   0.438
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            6197
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         74.210
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             5994
_reflns_number_gt                4192
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  24o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.48      96     96    100.0     1.12     244.7   57.41  0.0236  0.0091
3.48 - 2.27     224    225     99.6     1.08     109.0   34.36  0.0130  0.0186
2.27 - 1.78     312    321     97.2     1.03      66.2   27.33  0.0263  0.0253
1.78 - 1.54     329    335     98.2     1.02      31.7   21.84  0.0203  0.0325
1.54 - 1.39     319    326     97.9     1.02      29.5   19.34  0.0273  0.0371
1.39 - 1.29     311    323     96.3     1.00      21.1   17.51  0.0213  0.0422
1.29 - 1.21     323    332     97.3     1.01      18.8   15.65  0.0345  0.0465
1.21 - 1.15     301    314     95.9     0.98      17.6   14.54  0.0414  0.0522
1.15 - 1.09     367    379     96.8     1.00      13.9   13.14  0.0253  0.0587
1.09 - 1.05     297    318     93.4     0.96       9.2   11.27  0.0358  0.0776
1.05 - 1.01     321    343     93.6     0.97       7.4    9.26  0.0438  0.0921
1.01 - 0.98     289    311     92.9     0.96       5.9    8.76  0.0601  0.1101
0.98 - 0.95     320    347     92.2     0.95       4.1    6.29  0.0766  0.1552
0.95 - 0.92     360    381     94.5     0.97       3.6    6.08  0.0881  0.1649
0.92 - 0.90     283    302     93.7     0.96       3.2    6.01  0.0884  0.1698
0.90 - 0.88     307    319     96.2     0.98       2.5    4.99  0.0364  0.2176
0.88 - 0.86     330    347     95.1     0.98       1.8    4.26  0.0967  0.2766
0.86 - 0.84     360    366     98.4     1.00       1.5    3.40  0.1048  0.3589
0.84 - 0.82     426    430     99.1     1.02       1.1    2.99  0.0868  0.4222
0.82 - 0.81     229    230     99.6     1.02       1.0    2.61  0.1840  0.4455
0.81 - 0.80     218    218    100.0     1.01       0.9    2.43  0.7538  0.5170
#--------------------------------------------------------------------------------
0.90 - 0.80    1870   1910     97.9     1.00       1.5    3.51  0.0896  0.3305
 Inf - 0.80    6322   6563     96.3     1.00      19.7   12.04  0.0233  0.0412
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0844P)²+0.3347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_number_reflns         5994
_refine_ls_number_parameters     386
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.060

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.92066(4) 0.25165(7) 0.88933(4) 0.0515(2) Uani 1 1 d . . . . .
S12 S 0.85642(6) 0.27576(10) 1.02831(5) 0.0747(3) Uani 1 1 d . . . . .
O11 O 0.97997(13) 0.2221(2) 0.85375(12) 0.0650(6) Uani 1 1 d . . . . .
O12 O 0.92147(14) 0.3852(2) 0.91671(12) 0.0643(6) Uani 1 1 d . . . . .
N11 N 0.56438(17) 0.1321(3) 0.68035(18) 0.0752(8) Uani 1 1 d D . . . .
H10 H 0.520(2) 0.154(4) 0.688(2) 0.113 Uiso 1 1 d D U . . .
H11 H 0.556(2) 0.068(3) 0.652(2) 0.113 Uiso 1 1 d D U . . .
N12 N 0.94582(15) 0.1431(2) 0.95417(13) 0.0535(6) Uani 1 1 d . . . . .
N13 N 0.94376(16) 0.0631(3) 1.06251(13) 0.0571(6) Uani 1 1 d . . . . .
H17 H 0.976015 -0.004303 1.062393 0.086 Uiso 1 1 calc R U . . .
C11 C 0.64663(17) 0.1592(3) 0.72981(16) 0.0512(6) Uani 1 1 d . . . . .
C12 C 0.71912(19) 0.0951(3) 0.72417(17) 0.0570(7) Uani 1 1 d . . . . .
H12 H 0.711142 0.033349 0.687061 0.068 Uiso 1 1 calc R U . . .
C13 C 0.80186(19) 0.1228(3) 0.77310(16) 0.0537(7) Uani 1 1 d . . . . .
H13 H 0.849548 0.078922 0.769278 0.064 Uiso 1 1 calc R U . . .
C14 C 0.81490(17) 0.2157(3) 0.82815(15) 0.0474(6) Uani 1 1 d . . . . .
C15 C 0.74276(18) 0.2799(3) 0.83399(15) 0.0491(6) Uani 1 1 d . . . . .
H15 H 0.750834 0.341831 0.870996 0.059 Uiso 1 1 calc R U . . .
C16 C 0.66040(18) 0.2518(3) 0.78547(15) 0.0506(6) Uani 1 1 d . . . . .
H16 H 0.612809 0.295228 0.789717 0.061 Uiso 1 1 calc R U . . .
C17 C 0.92039(18) 0.1550(3) 1.00967(15) 0.0504(6) Uani 1 1 d . . . . .
C18 C 0.9129(2) 0.0834(4) 1.11713(17) 0.0707(9) Uani 1 1 d . . . . .
H18 H 0.925181 0.027046 1.157166 0.085 Uiso 1 1 calc R U . . .
C19 C 0.8635(3) 0.1923(4) 1.10634(18) 0.0793(10) Uani 1 1 d . . . . .
H19 H 0.836178 0.220131 1.137203 0.095 Uiso 1 1 calc R U . . .
S21 S 0.44240(5) 0.17586(7) 0.83725(4) 0.0525(2) Uani 1 1 d . . . . .
S22 S 0.54493(6) 0.16782(10) 1.01398(5) 0.0739(3) Uani 1 1 d . . . . .
O21 O 0.43742(14) 0.1718(2) 0.76324(11) 0.0665(6) Uani 1 1 d . . . . .
O22 O 0.45216(14) 0.0494(2) 0.87409(12) 0.0634(5) Uani 1 1 d . . . . .
N21 N 0.10903(19) 0.4134(4) 0.8235(2) 0.0863(10) Uani 1 1 d D . . . .
H20 H 0.074(2) 0.357(4) 0.826(3) 0.129 Uiso 1 1 d D U . . .
H21 H 0.086(3) 0.474(4) 0.793(2) 0.129 Uiso 1 1 d D U . . .
N22 N 0.51823(16) 0.2793(2) 0.87834(13) 0.0550(6) Uani 1 1 d . . . . .
N23 N 0.61712(17) 0.3701(3) 0.98456(15) 0.0644(7) Uani 1 1 d . . . . .
H27 H 0.632576 0.432130 0.961855 0.097 Uiso 1 1 calc R U . . .
C21 C 0.1852(2) 0.3568(3) 0.82603(17) 0.0582(7) Uani 1 1 d . . . . .
C22 C 0.2333(2) 0.4138(3) 0.78895(17) 0.0597(7) Uani 1 1 d . . . . .
H22 H 0.212149 0.490021 0.760902 0.072 Uiso 1 1 calc R U . . .
C23 C 0.3109(2) 0.3599(3) 0.79289(16) 0.0579(7) Uani 1 1 d . . . . .
H23 H 0.341657 0.399694 0.767422 0.069 Uiso 1 1 calc R U . . .
C24 C 0.34445(19) 0.2464(3) 0.83457(15) 0.0515(6) Uani 1 1 d . . . . .
C25 C 0.2973(2) 0.1885(3) 0.8716(2) 0.0689(9) Uani 1 1 d . . . . .
H25 H 0.318572 0.112045 0.899434 0.083 Uiso 1 1 calc R U . . .
C26 C 0.2191(2) 0.2431(4) 0.8675(2) 0.0757(10) Uani 1 1 d . . . . .
H26 H 0.188455 0.203130 0.892980 0.091 Uiso 1 1 calc R U . . .
C27 C 0.55679(19) 0.2782(3) 0.95010(16) 0.0535(7) Uani 1 1 d . . . . .
C28 C 0.6527(2) 0.3572(4) 1.0599(2) 0.0790(10) Uani 1 1 d . . . . .
H28 H 0.695067 0.414837 1.090212 0.095 Uiso 1 1 calc R U . . .
C29 C 0.6209(3) 0.2551(5) 1.08457(19) 0.0859(12) Uani 1 1 d . . . . .
H29 H 0.637344 0.233366 1.133617 0.103 Uiso 1 1 calc R U . . .
O30 O 0.69324(15) 0.5381(2) 0.92181(14) 0.0710(6) Uani 1 1 d . . . . .
N30 N 0.76165(19) 0.7352(3) 0.93260(16) 0.0687(7) Uani 1 1 d . . . . .
N31 N 0.61384(19) 0.7169(3) 0.86392(17) 0.0721(8) Uani 1 1 d . . . . .
C30 C 0.6892(2) 0.6601(3) 0.90694(17) 0.0560(7) Uani 1 1 d . . . . .
C31 C 0.6059(3) 0.8559(4) 0.8418(3) 0.1023(14) Uani 1 1 d . . . . .
H31A H 0.548715 0.889311 0.836562 0.123 Uiso 1 1 calc R U . . .
H31B H 0.611456 0.863729 0.794965 0.123 Uiso 1 1 calc R U . . .
C32 C 0.6743(4) 0.9363(4) 0.8966(3) 0.126(2) Uani 1 1 d . . . . .
H32A H 0.662547 0.941628 0.940935 0.151 Uiso 1 1 calc R U . . .
H32B H 0.673806 1.026419 0.878301 0.151 Uiso 1 1 calc R U . . .
C33 C 0.7619(4) 0.8745(4) 0.9131(3) 0.1135(17) Uani 1 1 d . . . . .
H33A H 0.777478 0.881853 0.870648 0.136 Uiso 1 1 calc R U . . .
H33B H 0.805482 0.922377 0.952956 0.136 Uiso 1 1 calc R U . . .
C34 C 0.5370(2) 0.6326(5) 0.8299(3) 0.0988(14) Uani 1 1 d . . . . .
H34A H 0.498042 0.674562 0.786059 0.148 Uiso 1 1 calc R U . . .
H34B H 0.507580 0.620813 0.863051 0.148 Uiso 1 1 calc R U . . .
H34C H 0.554689 0.547026 0.818344 0.148 Uiso 1 1 calc R U . . .
C35 C 0.8454(2) 0.6728(4) 0.9720(2) 0.0904(12) Uani 1 1 d . . . . .
H35A H 0.879158 0.728642 1.012272 0.136 Uiso 1 1 calc R U . . .
H35B H 0.876220 0.661341 0.939901 0.136 Uiso 1 1 calc R U . . .
H35C H 0.836477 0.587149 0.989935 0.136 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.439(2) . ?
S11 O12 1.439(2) . ?
S11 N12 1.611(2) . ?
S11 C14 1.746(3) . ?
S12 C19 1.721(4) . ?
S12 C17 1.734(3) . ?
N11 C11 1.369(4) . ?
N11 H10 0.84(2) . ?
N11 H11 0.83(2) . ?
N12 C17 1.323(3) . ?
N13 C17 1.335(3) . ?
N13 C18 1.375(4) . ?
N13 H17 0.8600 . ?
C11 C16 1.391(4) . ?
C11 C12 1.401(4) . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.397(4) . ?
C15 C16 1.366(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.329(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
S21 O22 1.437(2) . ?
S21 O21 1.438(2) . ?
S21 N22 1.590(2) . ?
S21 C24 1.748(3) . ?
S22 C29 1.721(4) . ?
S22 C27 1.745(3) . ?
N21 C21 1.364(4) . ?
N21 H20 0.83(2) . ?
N21 H21 0.83(2) . ?
N22 C27 1.319(4) . ?
N23 C27 1.337(4) . ?
N23 C28 1.387(4) . ?
N23 H27 0.8600 . ?
C21 C26 1.391(5) . ?
C21 C22 1.392(4) . ?
C22 C23 1.366(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.383(4) . ?
C25 C26 1.377(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C28 C29 1.324(5) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
O30 C30 1.250(3) . ?
N30 C30 1.341(4) . ?
N30 C33 1.446(5) . ?
N30 C35 1.448(5) . ?
N31 C30 1.340(4) . ?
N31 C31 1.448(5) . ?
N31 C34 1.460(5) . ?
C31 C32 1.474(7) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.493(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.69(14) . . ?
O11 S11 N12 103.53(13) . . ?
O12 S11 N12 111.21(13) . . ?
O11 S11 C14 107.86(13) . . ?
O12 S11 C14 108.45(13) . . ?
N12 S11 C14 107.63(13) . . ?
C19 S12 C17 90.83(16) . . ?
C11 N11 H10 121(3) . . ?
C11 N11 H11 120(3) . . ?
H10 N11 H11 113.5(18) . . ?
C17 N12 S11 122.3(2) . . ?
C17 N13 C18 115.6(3) . . ?
C17 N13 H17 122.2 . . ?
C18 N13 H17 122.2 . . ?
N11 C11 C16 121.3(3) . . ?
N11 C11 C12 120.0(3) . . ?
C16 C11 C12 118.7(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 S11 120.0(2) . . ?
C15 C14 S11 120.7(2) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N12 C17 N13 120.0(3) . . ?
N12 C17 S12 130.6(2) . . ?
N13 C17 S12 109.3(2) . . ?
C19 C18 N13 112.5(3) . . ?
C19 C18 H18 123.8 . . ?
N13 C18 H18 123.8 . . ?
C18 C19 S12 111.8(3) . . ?
C18 C19 H19 124.1 . . ?
S12 C19 H19 124.1 . . ?
O22 S21 O21 116.43(14) . . ?
O22 S21 N22 113.36(13) . . ?
O21 S21 N22 105.64(13) . . ?
O22 S21 C24 107.12(13) . . ?
O21 S21 C24 106.60(14) . . ?
N22 S21 C24 107.16(14) . . ?
C29 S22 C27 91.21(17) . . ?
C21 N21 H20 112(3) . . ?
C21 N21 H21 120(3) . . ?
H20 N21 H21 113.4(19) . . ?
C27 N22 S21 120.8(2) . . ?
C27 N23 C28 114.6(3) . . ?
C27 N23 H27 122.7 . . ?
C28 N23 H27 122.7 . . ?
N21 C21 C26 121.4(3) . . ?
N21 C21 C22 121.0(3) . . ?
C26 C21 C22 117.6(3) . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 118.6(3) . . ?
C25 C24 S21 121.1(2) . . ?
C23 C24 S21 120.2(2) . . ?
C26 C25 C24 120.5(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C21 121.2(3) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
N22 C27 N23 120.5(3) . . ?
N22 C27 S22 130.2(2) . . ?
N23 C27 S22 109.3(2) . . ?
C29 C28 N23 113.8(3) . . ?
C29 C28 H28 123.1 . . ?
N23 C28 H28 123.1 . . ?
C28 C29 S22 111.1(3) . . ?
C28 C29 H29 124.4 . . ?
S22 C29 H29 124.4 . . ?
C30 N30 C33 122.1(3) . . ?
C30 N30 C35 119.9(3) . . ?
C33 N30 C35 117.4(3) . . ?
C30 N31 C31 123.7(3) . . ?
C30 N31 C34 119.1(3) . . ?
C31 N31 C34 116.8(3) . . ?
O30 C30 N31 121.2(3) . . ?
O30 C30 N30 119.8(3) . . ?
N31 C30 N30 119.1(3) . . ?
N31 C31 C32 110.1(4) . . ?
N31 C31 H31A 109.6 . . ?
C32 C31 H31A 109.6 . . ?
N31 C31 H31B 109.6 . . ?
C32 C31 H31B 109.6 . . ?
H31A C31 H31B 108.2 . . ?
C31 C32 C33 110.2(4) . . ?
C31 C32 H32A 109.6 . . ?
C33 C32 H32A 109.6 . . ?
C31 C32 H32B 109.6 . . ?
C33 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
N30 C33 C32 110.8(4) . . ?
N30 C33 H33A 109.5 . . ?
C32 C33 H33A 109.5 . . ?
N30 C33 H33B 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
N31 C34 H34A 109.5 . . ?
N31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N30 C35 H35A 109.5 . . ?
N30 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N30 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 164.2(2) . . . . ?
O12 S11 N12 C17 36.9(3) . . . . ?
C14 S11 N12 C17 -81.7(3) . . . . ?
N11 C11 C12 C13 179.3(3) . . . . ?
C16 C11 C12 C13 0.5(5) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C12 C13 C14 S11 -179.2(2) . . . . ?
O11 S11 C14 C13 25.2(3) . . . . ?
O12 S11 C14 C13 153.7(2) . . . . ?
N12 S11 C14 C13 -85.9(3) . . . . ?
O11 S11 C14 C15 -154.7(2) . . . . ?
O12 S11 C14 C15 -26.2(3) . . . . ?
N12 S11 C14 C15 94.2(2) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
S11 C14 C15 C16 179.5(2) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
N11 C11 C16 C15 -179.0(3) . . . . ?
C12 C11 C16 C15 -0.2(4) . . . . ?
S11 N12 C17 N13 -179.2(2) . . . . ?
S11 N12 C17 S12 1.6(4) . . . . ?
C18 N13 C17 N12 -179.0(3) . . . . ?
C18 N13 C17 S12 0.4(3) . . . . ?
C19 S12 C17 N12 178.2(3) . . . . ?
C19 S12 C17 N13 -1.0(2) . . . . ?
C17 N13 C18 C19 0.8(4) . . . . ?
N13 C18 C19 S12 -1.6(4) . . . . ?
C17 S12 C19 C18 1.5(3) . . . . ?
O22 S21 N22 C27 -31.5(3) . . . . ?
O21 S21 N22 C27 -160.2(2) . . . . ?
C24 S21 N22 C27 86.4(3) . . . . ?
N21 C21 C22 C23 178.0(3) . . . . ?
C26 C21 C22 C23 0.2(5) . . . . ?
C21 C22 C23 C24 -0.3(5) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C22 C23 C24 S21 178.3(2) . . . . ?
O22 S21 C24 C25 7.3(3) . . . . ?
O21 S21 C24 C25 132.6(3) . . . . ?
N22 S21 C24 C25 -114.7(3) . . . . ?
O22 S21 C24 C23 -170.5(2) . . . . ?
O21 S21 C24 C23 -45.2(3) . . . . ?
N22 S21 C24 C23 67.5(3) . . . . ?
C23 C24 C25 C26 -0.5(5) . . . . ?
S21 C24 C25 C26 -178.3(3) . . . . ?
C24 C25 C26 C21 0.4(6) . . . . ?
N21 C21 C26 C25 -178.1(4) . . . . ?
C22 C21 C26 C25 -0.2(6) . . . . ?
S21 N22 C27 N23 -176.3(2) . . . . ?
S21 N22 C27 S22 5.6(4) . . . . ?
C28 N23 C27 N22 -179.7(3) . . . . ?
C28 N23 C27 S22 -1.2(4) . . . . ?
C29 S22 C27 N22 179.7(3) . . . . ?
C29 S22 C27 N23 1.4(3) . . . . ?
C27 N23 C28 C29 0.3(5) . . . . ?
N23 C28 C29 S22 0.8(5) . . . . ?
C27 S22 C29 C28 -1.3(3) . . . . ?
C31 N31 C30 O30 -176.8(4) . . . . ?
C34 N31 C30 O30 -4.3(5) . . . . ?
C31 N31 C30 N30 1.3(5) . . . . ?
C34 N31 C30 N30 173.8(3) . . . . ?
C33 N30 C30 O30 175.7(4) . . . . ?
C35 N30 C30 O30 5.3(5) . . . . ?
C33 N30 C30 N31 -2.5(5) . . . . ?
C35 N30 C30 N31 -172.8(3) . . . . ?
C30 N31 C31 C32 -26.8(6) . . . . ?
C34 N31 C31 C32 160.6(4) . . . . ?
N31 C31 C32 C33 51.3(6) . . . . ?
C30 N30 C33 C32 28.8(6) . . . . ?
C35 N30 C33 C32 -160.7(4) . . . . ?
C31 C32 C33 N30 -52.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O21 0.84(2) 2.37(3) 3.142(4) 153(4) . yes
N11 H11 O12 0.83(2) 2.39(2) 3.191(4) 163(3) 2_646 yes
N13 H17 N12 0.86 2.01 2.854(3) 168.8 3_757 yes
N21 H20 O11 0.83(2) 2.27(2) 3.088(4) 169(5) 1_455 yes
N21 H21 O21 0.83(2) 2.23(3) 3.036(4) 161(4) 2_556 yes
N23 H27 O30 0.86 1.83 2.671(3) 164.4 . yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12
_database_code_depnum_ccdc_archive 'CCDC 2120774'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 13o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_12                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.10 angstrom and below 1sigma(I) around 1.00
angstrom. For the refinement, the data are truncated at 0.95 angstrom
resolution.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 5-Methyl-2(3H)-furanone (1:1) solvate'
_chemical_name_common            'Sulfathiazole, alpha-angelica lactone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C5 H6 O2'
_chemical_formula_sum            'C14 H15 N3 O4 S2'
_chemical_formula_weight         353.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.194(2)
_cell_length_b                   21.111(4)
_cell_length_c                   9.570(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.20(3)
_cell_angle_gamma                90
_cell_volume                     1651.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5433
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      21.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.345
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5433
_diffrn_reflns_av_unetI/netI     0.1760
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.929
_diffrn_reflns_theta_max         21.967
_diffrn_reflns_theta_full        21.967
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1932
_reflns_number_gt                793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  13o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.75      37     41     90.2     3.71     820.7   51.94  0.0722  0.0138
3.75 - 2.46      86     87     98.9     3.29     387.5   21.74  0.0849  0.0315
2.46 - 1.95     124    126     98.4     3.10     137.7    9.95  0.0469  0.0782
1.95 - 1.69     126    129     97.7     3.15     102.3    7.40  0.0449  0.1030
1.69 - 1.54     119    123     96.7     3.02      63.7    5.38  0.0607  0.1537
1.54 - 1.42     129    132     97.7     3.12      50.4    4.29  0.0775  0.1860
1.42 - 1.33     134    136     98.5     2.96      41.4    3.54  0.0870  0.2524
1.33 - 1.27     121    122     99.2     2.93      27.2    2.53  0.1197  0.3416
1.27 - 1.21     128    130     98.5     2.84      32.3    2.64  0.1079  0.3265
1.21 - 1.16     127    132     96.2     2.59      30.7    2.20  0.1189  0.3801
1.16 - 1.12     131    137     95.6     2.54      24.0    1.87  0.1439  0.5007
1.12 - 1.09     102    106     96.2     2.45      19.6    1.55  0.1687  0.6237
1.09 - 1.05     156    162     96.3     2.34      16.6    1.29  0.1947  0.7466
1.05 - 1.03      78     84     92.9     2.08      14.6    1.07  0.2259  0.9060
1.03 - 1.00     131    148     88.5     2.04      10.4    0.86  0.2542  1.2075
1.00 - 0.97     149    174     85.6     1.91       7.6    0.68  0.3374  1.5824
0.97 - 0.95     110    122     90.2     1.80       7.7    0.63  0.3107  1.7288
0.95 - 0.93     127    139     91.4     1.73       7.1    0.55  0.3083  1.9349
0.93 - 0.91     130    150     86.7     1.64       8.0    0.61  0.3060  1.7396
0.91 - 0.89      98    163     60.1     0.99       6.0    0.48  0.2594  2.2449
0.89 - 0.85     121    378     32.0     0.46       5.2    0.40  0.2788  2.5592
0.85 - 0.84       3    109      2.8     0.03       2.1    0.14  0.0000  7.2903
#--------------------------------------------------------------------------------
0.94 - 0.84     413    867     47.6     0.81       6.4    0.50  0.2980  2.1072
 Inf - 0.84    2467   3030     81.4     2.09      56.7    3.96  0.0840  0.2077
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The H atoms of the NH2 group could not readily be refined, so they were
placed in-plane and allowed to ride. This is an approximation.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1932
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   0.698
_refine_ls_restrained_S_all      0.698
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.046

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.57218(18) 0.14423(7) 0.40421(19) 0.0674(5) Uani 1 1 d . . . . .
S12 S 0.6614(2) 0.13193(9) 0.7437(2) 0.1213(9) Uani 1 1 d . . . . .
O11 O 0.5606(4) 0.12478(18) 0.2575(4) 0.0799(13) Uani 1 1 d . . . . .
O12 O 0.7128(4) 0.18061(17) 0.4561(4) 0.0886(15) Uani 1 1 d . . . . .
N11 N -0.0261(5) 0.2804(2) 0.5280(5) 0.0871(17) Uani 1 1 d . . . . .
H10 H -0.022354 0.311309 0.589791 0.131 Uiso 1 1 d R U . . .
H11 H -0.120564 0.268679 0.486211 0.131 Uiso 1 1 d R U . . .
N12 N 0.5594(5) 0.07838(19) 0.4899(5) 0.0583(13) Uani 1 1 d . . . . .
N13 N 0.5734(5) 0.0208(2) 0.6903(5) 0.0745(15) Uani 1 1 d . . . . .
H17 H 0.538680 -0.013643 0.645742 0.112 Uiso 1 1 calc R U . . .
C11 C 0.1150(8) 0.2504(3) 0.4970(6) 0.0564(16) Uani 1 1 d . . . . .
C12 C 0.1088(7) 0.2016(3) 0.3995(6) 0.0626(17) Uani 1 1 d . . . . .
H12 H 0.006940 0.189801 0.352976 0.075 Uiso 1 1 calc R U . . .
C13 C 0.2485(8) 0.1704(3) 0.3702(6) 0.0664(18) Uani 1 1 d . . . . .
H13 H 0.243152 0.136398 0.305011 0.080 Uiso 1 1 calc R U . . .
C14 C 0.3989(7) 0.1885(2) 0.4358(6) 0.0507(14) Uani 1 1 d . . . . .
C15 C 0.4049(7) 0.2380(3) 0.5301(6) 0.0597(17) Uani 1 1 d . . . . .
H15 H 0.506999 0.250601 0.575025 0.072 Uiso 1 1 calc R U . . .
C16 C 0.2658(8) 0.2690(3) 0.5592(6) 0.0600(16) Uani 1 1 d . . . . .
H16 H 0.271919 0.303704 0.622682 0.072 Uiso 1 1 calc R U . . .
C17 C 0.5921(7) 0.0756(3) 0.6235(7) 0.0610(17) Uani 1 1 d . . . . .
C18 C 0.6110(9) 0.0214(4) 0.8306(8) 0.114(3) Uani 1 1 d . . . . .
H18 H 0.605504 -0.014953 0.888649 0.136 Uiso 1 1 calc R U . . .
C19 C 0.6554(10) 0.0772(4) 0.8772(8) 0.143(3) Uani 1 1 d . . . . .
H19 H 0.681363 0.086671 0.973255 0.172 Uiso 1 1 calc R U . . .
O30 O 0.1251(5) 0.0421(3) 0.8992(7) 0.1114(17) Uani 1 1 d . . . . .
O31 O 0.1737(8) 0.1288(3) 1.0413(7) 0.161(3) Uani 1 1 d . . . . .
C30 C 0.1487(9) 0.1081(5) 0.9221(11) 0.105(3) Uani 1 1 d . . . . .
C31 C 0.1436(10) 0.1391(4) 0.7908(11) 0.147(3) Uani 1 1 d . . . . .
H31A H 0.248722 0.160112 0.775486 0.177 Uiso 1 1 calc R U . . .
H31B H 0.053786 0.170471 0.780755 0.177 Uiso 1 1 calc R U . . .
C32 C 0.1108(13) 0.0809(7) 0.6895(10) 0.184(5) Uani 1 1 d . . . . .
H32 H 0.100166 0.082755 0.590109 0.221 Uiso 1 1 calc R U . . .
C33 C 0.1012(11) 0.0330(5) 0.7606(11) 0.116(3) Uani 1 1 d . . . . .
C34 C 0.0664(8) -0.0325(4) 0.7215(9) 0.157(4) Uani 1 1 d . . . . .
H34A H -0.021803 -0.048618 0.775474 0.235 Uiso 1 1 calc R U . . .
H34B H 0.164965 -0.058179 0.741540 0.235 Uiso 1 1 calc R U . . .
H34C H 0.032773 -0.034720 0.621251 0.235 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.442(3) . ?
S11 O11 1.459(4) . ?
S11 N12 1.621(4) . ?
S11 C14 1.745(5) . ?
S12 C17 1.722(6) . ?
S12 C19 1.726(8) . ?
N11 C11 1.369(6) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.289(7) . ?
N13 C17 1.335(6) . ?
N13 C18 1.356(7) . ?
N13 H17 0.8800 . ?
C11 C12 1.388(7) . ?
C11 C16 1.389(6) . ?
C12 C13 1.368(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(7) . ?
C15 C16 1.361(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.302(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C33 1.341(9) . ?
O30 C30 1.421(9) . ?
O31 C30 1.225(8) . ?
C30 C31 1.414(10) . ?
C31 C32 1.574(12) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.224(11) . ?
C32 H32 0.9500 . ?
C33 C34 1.455(10) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 118.3(2) . . ?
O12 S11 N12 111.2(3) . . ?
O11 S11 N12 104.1(3) . . ?
O12 S11 C14 107.2(3) . . ?
O11 S11 C14 108.7(3) . . ?
N12 S11 C14 106.7(2) . . ?
C17 S12 C19 90.3(3) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 121.7(5) . . ?
C17 N13 C18 116.2(6) . . ?
C17 N13 H17 121.9 . . ?
C18 N13 H17 121.9 . . ?
N11 C11 C12 119.9(6) . . ?
N11 C11 C16 121.0(6) . . ?
C12 C11 C16 119.1(5) . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.1(5) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 S11 121.9(5) . . ?
C13 C14 S11 118.6(5) . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.5(5) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N12 C17 N13 119.5(6) . . ?
N12 C17 S12 131.7(5) . . ?
N13 C17 S12 108.8(5) . . ?
C19 C18 N13 112.6(7) . . ?
C19 C18 H18 123.7 . . ?
N13 C18 H18 123.7 . . ?
C18 C19 S12 112.0(6) . . ?
C18 C19 H19 124.0 . . ?
S12 C19 H19 124.0 . . ?
C33 O30 C30 107.5(7) . . ?
O31 C30 C31 130.8(11) . . ?
O31 C30 O30 120.3(10) . . ?
C31 C30 O30 108.8(8) . . ?
C30 C31 C32 100.3(8) . . ?
C30 C31 H31A 111.7 . . ?
C32 C31 H31A 111.7 . . ?
C30 C31 H31B 111.7 . . ?
C32 C31 H31B 111.7 . . ?
H31A C31 H31B 109.5 . . ?
C33 C32 C31 108.5(10) . . ?
C33 C32 H32 125.8 . . ?
C31 C32 H32 125.8 . . ?
C32 C33 O30 114.9(11) . . ?
C32 C33 C34 131.4(12) . . ?
O30 C33 C34 113.7(9) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 39.8(5) . . . . ?
O11 S11 N12 C17 168.3(4) . . . . ?
C14 S11 N12 C17 -76.8(5) . . . . ?
N11 C11 C12 C13 -178.5(5) . . . . ?
C16 C11 C12 C13 3.0(8) . . . . ?
C11 C12 C13 C14 -1.5(8) . . . . ?
C12 C13 C14 C15 -0.1(8) . . . . ?
C12 C13 C14 S11 175.9(4) . . . . ?
O12 S11 C14 C15 -17.3(5) . . . . ?
O11 S11 C14 C15 -146.4(4) . . . . ?
N12 S11 C14 C15 101.9(5) . . . . ?
O12 S11 C14 C13 166.8(4) . . . . ?
O11 S11 C14 C13 37.8(5) . . . . ?
N12 S11 C14 C13 -74.0(5) . . . . ?
C13 C14 C15 C16 0.1(8) . . . . ?
S11 C14 C15 C16 -175.7(4) . . . . ?
C14 C15 C16 C11 1.5(8) . . . . ?
N11 C11 C16 C15 178.5(5) . . . . ?
C12 C11 C16 C15 -3.0(8) . . . . ?
S11 N12 C17 N13 177.3(4) . . . . ?
S11 N12 C17 S12 -3.2(8) . . . . ?
C18 N13 C17 N12 179.6(6) . . . . ?
C18 N13 C17 S12 0.0(7) . . . . ?
C19 S12 C17 N12 179.1(6) . . . . ?
C19 S12 C17 N13 -1.3(5) . . . . ?
C17 N13 C18 C19 1.9(10) . . . . ?
N13 C18 C19 S12 -2.8(10) . . . . ?
C17 S12 C19 C18 2.4(7) . . . . ?
C33 O30 C30 O31 -179.8(8) . . . . ?
C33 O30 C30 C31 -1.9(9) . . . . ?
O31 C30 C31 C32 178.4(10) . . . . ?
O30 C30 C31 C32 0.8(9) . . . . ?
C30 C31 C32 C33 0.6(12) . . . . ?
C31 C32 C33 O30 -1.9(14) . . . . ?
C31 C32 C33 C34 177.3(8) . . . . ?
C30 O30 C33 C32 2.4(12) . . . . ?
C30 O30 C33 C34 -176.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.88 2.17 3.018(6) 162.4 4_566 yes
N11 H11 O12 0.88 2.31 3.045(6) 140.7 1_455 yes
N13 H17 S11 0.88 2.93 3.771(5) 160.4 3_656 yes
N13 H17 N12 0.88 2.01 2.875(6) 166.9 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 2120781'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 8o
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, 4-butyrolactone (1:1) solvate'
_chemical_name_common            'Sulfathiazole, gamma-butyrolactone'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H6 O2'
_chemical_formula_sum            'C13 H15 N3 O4 S2'
_chemical_formula_weight         341.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.636(2)
_cell_length_b                   19.187(4)
_cell_length_c                   9.354(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.03(3)
_cell_angle_gamma                90
_cell_volume                     1549.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      4.61
_cell_measurement_theta_max      74.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    3.318
_shelx_estimated_absorpt_T_min   0.436
_shelx_estimated_absorpt_T_max   0.436
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            3240
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         4.609
_diffrn_reflns_theta_max         74.232
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3059
_reflns_number_gt                1828
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  8o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.35      48     50     96.0     1.16     235.9   68.91  0.0156  0.0092
3.35 - 2.24     112    114     98.2     1.10      80.6   36.01  0.0069  0.0192
2.24 - 1.75     162    163     99.4     1.09      36.2   23.54  0.0377  0.0293
1.75 - 1.53     154    156     98.7     1.06      29.0   19.72  0.0139  0.0350
1.53 - 1.39     153    158     96.8     1.04      17.5   15.04  0.0480  0.0467
1.39 - 1.28     170    175     97.1     1.03      13.1   12.97  0.0280  0.0583
1.28 - 1.21     146    152     96.1     1.03      12.2   12.43  0.0189  0.0647
1.21 - 1.14     185    188     98.4     1.04      10.5   11.58  0.0198  0.0736
1.14 - 1.09     150    156     96.2     1.01       8.5   10.30  0.0558  0.0879
1.09 - 1.05     141    150     94.0     0.99       5.5    7.17  0.0500  0.1278
1.05 - 1.01     174    188     92.6     0.95       4.0    5.49  0.0614  0.1752
1.01 - 0.98     141    150     94.0     1.00       2.7    4.54  0.1530  0.2309
0.98 - 0.95     161    173     93.1     0.98       2.8    4.64  0.0816  0.2213
0.95 - 0.92     175    186     94.1     0.97       2.1    4.03  0.0424  0.2749
0.92 - 0.90     155    160     96.9     1.01       1.5    3.22  0.1157  0.3660
0.90 - 0.88     141    154     91.6     0.95       1.4    3.03  0.1145  0.3960
0.88 - 0.86     156    161     96.9     1.02       1.1    2.67  0.1209  0.4491
0.86 - 0.84     204    206     99.0     1.04       0.8    2.13  0.1171  0.6016
0.84 - 0.83     104    105     99.0     1.04       0.5    1.40  0.1092  0.9308
0.83 - 0.81     222    223     99.6     1.02       0.7    1.93  0.2284  0.6742
0.81 - 0.80     101    103     98.1     1.04       0.6    1.78  0.2022  0.7138
#--------------------------------------------------------------------------------
0.90 - 0.80     928    952     97.5     1.02       0.9    2.19  0.1417  0.5600
 Inf - 0.80    3155   3271     96.5     1.02      14.0    9.76  0.0174  0.0514
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0878P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3059
_refine_ls_number_parameters     206
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1593
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.056

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 1.05362(11) 0.84518(5) 0.63606(10) 0.0578(3) Uani 1 1 d . . . . .
S12 S 1.13976(15) 0.84102(5) 0.29503(12) 0.0775(4) Uani 1 1 d . . . . .
O11 O 1.0512(4) 0.87129(15) 0.7797(3) 0.0750(8) Uani 1 1 d . . . . .
O12 O 1.1754(3) 0.79746(14) 0.5985(3) 0.0738(8) Uani 1 1 d . . . . .
N11 N 0.4522(4) 0.7112(2) 0.5081(6) 0.0947(14) Uani 1 1 d D . . . .
H10 H 0.441(6) 0.674(2) 0.457(6) 0.142 Uiso 1 1 d D U . . .
H11 H 0.367(5) 0.735(3) 0.513(6) 0.142 Uiso 1 1 d D U . . .
N12 N 1.0575(3) 0.91454(14) 0.5387(3) 0.0545(7) Uani 1 1 d . . . . .
N13 N 1.0748(3) 0.96833(16) 0.3196(3) 0.0572(7) Uani 1 1 d . . . . .
H17 H 1.049612 1.008163 0.354314 0.086 Uiso 1 1 calc R U . . .
C11 C 0.5917(5) 0.7427(2) 0.5366(5) 0.0669(10) Uani 1 1 d . . . . .
C12 C 0.5996(5) 0.8048(2) 0.6115(5) 0.0673(10) Uani 1 1 d . . . . .
H12 H 0.509044 0.826079 0.641640 0.081 Uiso 1 1 calc R U . . .
C13 C 0.7405(5) 0.83538(18) 0.6416(4) 0.0614(9) Uani 1 1 d . . . . .
H13 H 0.744371 0.877122 0.692021 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8777(4) 0.80450(17) 0.5973(4) 0.0527(8) Uani 1 1 d . . . . .
C15 C 0.8709(4) 0.74288(18) 0.5223(4) 0.0614(9) Uani 1 1 d . . . . .
H15 H 0.961597 0.722378 0.490471 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7305(5) 0.7115(2) 0.4941(5) 0.0673(10) Uani 1 1 d . . . . .
H16 H 0.727439 0.669026 0.446238 0.081 Uiso 1 1 calc R U . . .
C17 C 1.0869(4) 0.91115(17) 0.4003(4) 0.0511(8) Uani 1 1 d . . . . .
C18 C 1.1054(5) 0.9591(2) 0.1770(4) 0.0715(11) Uani 1 1 d . . . . .
H18 H 1.101940 0.995032 0.110278 0.086 Uiso 1 1 calc R U . . .
C19 C 1.1400(6) 0.8941(2) 0.1444(5) 0.0841(13) Uani 1 1 d . . . . .
H19 H 1.161771 0.878647 0.052726 0.101 Uiso 1 1 calc R U . . .
O30 O 0.5019(6) 0.43080(19) 0.6342(5) 0.1294(15) Uani 1 1 d . . . . .
O31 O 0.4601(6) 0.5095(3) 0.7946(6) 0.172(2) Uani 1 1 d . . . . .
C30 C 0.5427(6) 0.4817(3) 0.6973(6) 0.0836(13) Uani 1 1 d . . . . .
C31 C 0.5323(10) 0.5727(5) 0.8451(12) 0.217(6) Uani 1 1 d . . . . .
H31A H 0.475486 0.612773 0.808606 0.261 Uiso 1 1 calc R U . . .
H31B H 0.530714 0.574193 0.948718 0.261 Uiso 1 1 calc R U . . .
C32 C 0.6777(8) 0.5751(4) 0.8011(7) 0.134(2) Uani 1 1 d . . . . .
H32A H 0.749274 0.562694 0.878058 0.160 Uiso 1 1 calc R U . . .
H32B H 0.703251 0.621383 0.767019 0.160 Uiso 1 1 calc R U . . .
C33 C 0.6843(6) 0.5225(3) 0.6812(6) 0.1007(16) Uani 1 1 d . . . . .
H33A H 0.685571 0.545562 0.588847 0.121 Uiso 1 1 calc R U . . .
H33B H 0.775466 0.493263 0.690907 0.121 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.434(3) . ?
S11 O12 1.443(3) . ?
S11 N12 1.613(3) . ?
S11 C14 1.741(4) . ?
S12 C17 1.733(4) . ?
S12 C19 1.738(5) . ?
N11 C11 1.369(5) . ?
N11 H10 0.86(4) . ?
N11 H11 0.86(4) . ?
N12 C17 1.326(4) . ?
N13 C17 1.335(4) . ?
N13 C18 1.376(4) . ?
N13 H17 0.8600 . ?
C11 C12 1.385(5) . ?
C11 C16 1.403(5) . ?
C12 C13 1.375(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(5) . ?
C15 C16 1.375(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.320(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O30 C30 1.191(6) . ?
O31 C30 1.283(6) . ?
O31 C31 1.440(8) . ?
C30 C33 1.463(6) . ?
C31 C32 1.329(9) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.511(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.19(19) . . ?
O11 S11 N12 103.96(16) . . ?
O12 S11 N12 111.32(17) . . ?
O11 S11 C14 108.93(18) . . ?
O12 S11 C14 107.61(17) . . ?
N12 S11 C14 106.22(16) . . ?
C17 S12 C19 90.6(2) . . ?
C11 N11 H10 124(4) . . ?
C11 N11 H11 120(4) . . ?
H10 N11 H11 112.2(18) . . ?
C17 N12 S11 121.1(2) . . ?
C17 N13 C18 115.3(3) . . ?
C17 N13 H17 122.3 . . ?
C18 N13 H17 122.3 . . ?
N11 C11 C12 120.9(4) . . ?
N11 C11 C16 120.7(4) . . ?
C12 C11 C16 118.4(4) . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 S11 121.4(3) . . ?
C13 C14 S11 119.4(3) . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 120.9(4) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N12 C17 N13 119.8(3) . . ?
N12 C17 S12 130.5(3) . . ?
N13 C17 S12 109.6(3) . . ?
C19 C18 N13 113.2(4) . . ?
C19 C18 H18 123.4 . . ?
N13 C18 H18 123.4 . . ?
C18 C19 S12 111.3(3) . . ?
C18 C19 H19 124.4 . . ?
S12 C19 H19 124.4 . . ?
C30 O31 C31 109.9(5) . . ?
O30 C30 O31 121.9(6) . . ?
O30 C30 C33 129.0(6) . . ?
O31 C30 C33 109.1(5) . . ?
C32 C31 O31 109.5(6) . . ?
C32 C31 H31A 109.8 . . ?
O31 C31 H31A 109.8 . . ?
C32 C31 H31B 109.8 . . ?
O31 C31 H31B 109.8 . . ?
H31A C31 H31B 108.2 . . ?
C31 C32 C33 104.8(6) . . ?
C31 C32 H32A 110.8 . . ?
C33 C32 H32A 110.8 . . ?
C31 C32 H32B 110.8 . . ?
C33 C32 H32B 110.8 . . ?
H32A C32 H32B 108.9 . . ?
C30 C33 C32 103.8(5) . . ?
C30 C33 H33A 111.0 . . ?
C32 C33 H33A 111.0 . . ?
C30 C33 H33B 111.0 . . ?
C32 C33 H33B 111.0 . . ?
H33A C33 H33B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 168.3(3) . . . . ?
O12 S11 N12 C17 40.0(3) . . . . ?
C14 S11 N12 C17 -76.8(3) . . . . ?
N11 C11 C12 C13 178.9(4) . . . . ?
C16 C11 C12 C13 0.8(6) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C12 C13 C14 S11 179.4(3) . . . . ?
O11 S11 C14 C15 -138.8(3) . . . . ?
O12 S11 C14 C15 -9.6(4) . . . . ?
N12 S11 C14 C15 109.7(3) . . . . ?
O11 S11 C14 C13 42.0(3) . . . . ?
O12 S11 C14 C13 171.3(3) . . . . ?
N12 S11 C14 C13 -69.4(3) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
S11 C14 C15 C16 179.4(3) . . . . ?
C14 C15 C16 C11 2.3(6) . . . . ?
N11 C11 C16 C15 180.0(4) . . . . ?
C12 C11 C16 C15 -1.9(6) . . . . ?
S11 N12 C17 N13 173.6(2) . . . . ?
S11 N12 C17 S12 -5.3(5) . . . . ?
C18 N13 C17 N12 -179.0(3) . . . . ?
C18 N13 C17 S12 0.1(4) . . . . ?
C19 S12 C17 N12 178.3(4) . . . . ?
C19 S12 C17 N13 -0.7(3) . . . . ?
C17 N13 C18 C19 0.8(5) . . . . ?
N13 C18 C19 S12 -1.3(5) . . . . ?
C17 S12 C19 C18 1.1(4) . . . . ?
C31 O31 C30 O30 -176.0(7) . . . . ?
C31 O31 C30 C33 3.6(9) . . . . ?
C30 O31 C31 C32 -14.2(12) . . . . ?
O31 C31 C32 C33 17.5(11) . . . . ?
O30 C30 C33 C32 -173.8(6) . . . . ?
O31 C30 C33 C32 6.6(7) . . . . ?
C31 C32 C33 C30 -14.9(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O30 0.86(4) 2.24(4) 3.061(6) 158(5) 3_666 yes
N11 H11 O12 0.86(4) 2.21(4) 3.040(5) 161(5) 1_455 yes
N13 H17 S11 0.86 2.95 3.771(3) 159.5 3_776 yes
N13 H17 N12 0.86 2.02 2.858(4) 163.7 3_776 yes
C33 H33A O30 0.97 2.66 3.453(7) 139.5 3_666 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_17
_database_code_depnum_ccdc_archive 'CCDC 2120779'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 18o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_17                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Although the intensities appear to be strong, the available data
extend to 1.05 angstrom only. It could be that the data were never measured,
or that the resolution cut-off was applied during processing. The structure is
clearly of limited precision, but remains of value in the context of the set
of structures with which it is published. The coordinates also provide a 
suitable starting set for optimisation by DFT-D methods.
;
_vrf_PLAT029_17                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.903 Why?  
RESPONSE: The data are measured with a point-detector instrument. The missing
data are principally in the final resolution shells (1.10-1.05 angstrom). 
Up to 1.10 angstrom, the data are 99% complete. The limited resolution of the
data set is a more significant problem.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, cycloheptanone (1:1) solvate'
_chemical_name_common            'Sulfathiazole, cycloheptanone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C7 H12 O'
_chemical_formula_sum            'C16 H21 N3 O3 S2'
_chemical_formula_weight         367.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.613(3)
_cell_length_b                   12.074(3)
_cell_length_c                   22.085(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.440(1)
_cell_angle_gamma                90
_cell_volume                     1760.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      4.01
_cell_measurement_theta_max      47.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.914
_shelx_estimated_absorpt_T_min   0.475
_shelx_estimated_absorpt_T_max   0.759
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            1473
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.010
_diffrn_reflns_theta_max         47.137
_diffrn_reflns_theta_full        47.137
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.903
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.903
_reflns_number_total             1428
_reflns_number_gt                1295
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  18o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 4.77      23     24     95.8     1.04     425.0   88.68  0.0028  0.0071
4.77 - 3.08      53     53    100.0     1.08     527.3   75.82  0.0164  0.0071
3.08 - 2.43      75     75    100.0     1.04     231.9   44.79  0.0271  0.0138
2.43 - 2.09      79     79    100.0     1.05     169.5   35.29  0.0156  0.0178
2.09 - 1.91      74     75     98.7     1.04     133.5   31.52  0.0429  0.0197
1.91 - 1.75      77     77    100.0     1.01     100.5   30.15  0.0060  0.0238
1.75 - 1.64      73     73    100.0     1.04      80.1   26.49  0.0380  0.0263
1.64 - 1.56      81     82     98.8     1.02      77.0   26.35  0.0416  0.0285
1.56 - 1.49      74     75     98.7     1.01      49.3   22.93  0.0608  0.0325
1.49 - 1.43      81     82     98.8     1.02      43.8   20.69  0.0173  0.0325
1.43 - 1.37      80     80    100.0     1.01      42.2   21.56  0.0507  0.0347
1.37 - 1.33      64     66     97.0     1.00      28.6   19.26  0.0595  0.0383
1.33 - 1.29      86     90     95.6     0.98      39.0   18.46  0.0801  0.0373
1.29 - 1.26      60     60    100.0     1.03      38.6   19.06  0.0766  0.0374
1.26 - 1.23      90     90    100.0     1.03      34.4   19.36  0.0189  0.0382
1.23 - 1.20      73     74     98.6     1.00      35.3   18.80  0.0735  0.0377
1.20 - 1.17      82     84     97.6     1.00      34.7   18.10  0.0783  0.0396
1.17 - 1.15      59     61     96.7     0.98      26.4   15.96  0.0510  0.0459
1.15 - 1.12     100    100    100.0     1.01      20.6   14.76  0.0388  0.0510
1.12 - 1.10      71     73     97.3     1.00      20.0   14.17  0.5459  0.0533
1.10 - 1.07      52    135     38.5     0.39      18.5   14.78  0.0537  0.0530
1.07 - 1.05      10     84     11.9     0.12      18.1   14.76  0.0000  0.0571
#------------------------------------------------------------------------------
1.15 - 1.05     233    392     59.4     0.60      19.9   14.58  0.0456  0.0524
 Inf - 1.05    1517   1692     89.7     0.92      86.3   25.66  0.0248  0.0208
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The cycloheptanone solvate molecule shows large displacement ellipsoids.
Given the limited data resolution, no attempt was made to model disorder
or anisotropic ADPs. The solvent position should be viewed as indicative.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1828P)²+5.8929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.015(2)
_refine_ls_number_reflns         1428
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.1159
_refine_ls_wR_factor_ref         0.2878
_refine_ls_wR_factor_gt          0.2809
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.205

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.3284(4) 0.47335(19) 0.13683(10) 0.0664(13) Uani 1 1 d . . . . .
S12 S 0.0281(4) 0.6323(2) 0.05752(11) 0.0777(14) Uani 1 1 d . . . . .
O11 O 0.4499(11) 0.3819(5) 0.1499(3) 0.086(2) Uani 1 1 d . . . . .
O12 O 0.1146(10) 0.4660(5) 0.1471(3) 0.078(2) Uani 1 1 d . . . . .
N11 N 0.6501(14) 0.8240(8) 0.2883(4) 0.102(3) Uani 1 1 d . . . . .
H10 H 0.780152 0.840046 0.289711 0.154 Uiso 1 1 calc R U . . .
H11 H 0.568258 0.861516 0.310687 0.154 Uiso 1 1 calc R U . . .
N12 N 0.3676(12) 0.5021(6) 0.0674(3) 0.063(2) Uani 1 1 d . . . . .
N13 N 0.2947(13) 0.6049(7) -0.0178(4) 0.069(2) Uani 1 1 d . . . . .
H17 H 0.403744 0.582323 -0.035179 0.103 Uiso 1 1 calc R U . . .
C11 C 0.5777(18) 0.7436(8) 0.2525(4) 0.066(3) Uani 1 1 d . . . . .
C12 C 0.7010(15) 0.6845(9) 0.2175(5) 0.077(3) Uani 1 1 d . . . . .
H12 H 0.841131 0.702011 0.217612 0.092 Uiso 1 1 calc R U . . .
C13 C 0.6246(17) 0.6015(9) 0.1829(4) 0.069(3) Uani 1 1 d . . . . .
H13 H 0.712261 0.559426 0.159321 0.083 Uiso 1 1 calc R U . . .
C14 C 0.4246(15) 0.5766(7) 0.1810(4) 0.051(2) Uani 1 1 d . . . . .
C15 C 0.2986(16) 0.6346(9) 0.2150(5) 0.075(3) Uani 1 1 d . . . . .
H15 H 0.158258 0.617406 0.214054 0.090 Uiso 1 1 calc R U . . .
C16 C 0.3761(19) 0.7176(9) 0.2504(4) 0.079(3) Uani 1 1 d . . . . .
H16 H 0.288321 0.758939 0.274333 0.094 Uiso 1 1 calc R U . . .
C17 C 0.2484(14) 0.5713(8) 0.0379(4) 0.059(3) Uani 1 1 d . . . . .
C18 C 0.161(2) 0.6753(9) -0.0445(5) 0.081(3) Uani 1 1 d . . . . .
H18 H 0.172732 0.704434 -0.084130 0.097 Uiso 1 1 calc R U . . .
C19 C 0.0083(19) 0.7007(9) -0.0095(5) 0.085(3) Uani 1 1 d . . . . .
H19 H -0.097802 0.750857 -0.020913 0.102 Uiso 1 1 calc R U . . .
O30 O 0.705(5) 0.824(3) 0.0612(14) 0.363(14) Uiso 1 1 d . . . . .
C30 C 0.585(5) 0.868(2) 0.0895(12) 0.204(9) Uiso 1 1 d . . . . .
C31 C 0.395(3) 0.8593(17) 0.0947(9) 0.168(7) Uiso 1 1 d . . . . .
H31A H 0.375294 0.790090 0.117644 0.202 Uiso 1 1 calc R U . . .
H31B H 0.334882 0.846076 0.053184 0.202 Uiso 1 1 calc R U . . .
C32 C 0.277(5) 0.937(3) 0.1196(15) 0.292(14) Uiso 1 1 d . . . . .
H32A H 0.295888 0.928114 0.164120 0.350 Uiso 1 1 calc R U . . .
H32B H 0.134429 0.915953 0.108334 0.350 Uiso 1 1 calc R U . . .
C33 C 0.296(3) 1.056(2) 0.1063(10) 0.198(8) Uiso 1 1 d . . . . .
H33A H 0.275846 1.068109 0.062040 0.238 Uiso 1 1 calc R U . . .
H33B H 0.188455 1.097252 0.126137 0.238 Uiso 1 1 calc R U . . .
C34 C 0.489(3) 1.1003(18) 0.1269(9) 0.185(8) Uiso 1 1 d . . . . .
H34A H 0.490195 1.177230 0.111375 0.222 Uiso 1 1 calc R U . . .
H34B H 0.484246 1.106643 0.171512 0.222 Uiso 1 1 calc R U . . .
C35 C 0.685(3) 1.058(2) 0.1173(11) 0.202(8) Uiso 1 1 d . . . . .
H35A H 0.785399 1.098669 0.143885 0.242 Uiso 1 1 calc R U . . .
H35B H 0.716059 1.073411 0.074805 0.242 Uiso 1 1 calc R U . . .
C36 C 0.713(4) 0.940(2) 0.1283(12) 0.225(10) Uiso 1 1 d . . . . .
H36A H 0.686717 0.925096 0.171149 0.270 Uiso 1 1 calc R U . . .
H36B H 0.856498 0.921689 0.122741 0.270 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.386(7) . ?
S11 O12 1.448(7) . ?
S11 N12 1.608(8) . ?
S11 C14 1.684(9) . ?
S12 C19 1.693(11) . ?
S12 C17 1.711(10) . ?
N11 C11 1.324(12) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.297(11) . ?
N13 C18 1.339(12) . ?
N13 C17 1.348(11) . ?
N13 H17 0.8800 . ?
C11 C12 1.359(13) . ?
C11 C16 1.367(13) . ?
C12 C13 1.341(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.355(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.350(13) . ?
C15 C16 1.353(13) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.343(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C30 1.17(3) . ?
C30 C31 1.27(3) . ?
C30 C36 1.46(3) . ?
C31 C32 1.36(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.48(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.43(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.42(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.45(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.5(4) . . ?
O11 S11 N12 104.3(4) . . ?
O12 S11 N12 112.2(4) . . ?
O11 S11 C14 106.0(4) . . ?
O12 S11 C14 107.1(5) . . ?
N12 S11 C14 108.4(4) . . ?
C19 S12 C17 90.6(6) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 119.4(7) . . ?
C18 N13 C17 114.4(9) . . ?
C18 N13 H17 122.8 . . ?
C17 N13 H17 122.8 . . ?
N11 C11 C12 121.1(11) . . ?
N11 C11 C16 120.4(10) . . ?
C12 C11 C16 118.5(9) . . ?
C13 C12 C11 119.8(10) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.2(9) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.1(9) . . ?
C15 C14 S11 118.8(8) . . ?
C13 C14 S11 121.1(8) . . ?
C14 C15 C16 118.7(10) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C11 121.6(9) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
N12 C17 N13 119.2(8) . . ?
N12 C17 S12 130.5(7) . . ?
N13 C17 S12 110.2(7) . . ?
N13 C18 C19 113.0(10) . . ?
N13 C18 H18 123.5 . . ?
C19 C18 H18 123.5 . . ?
C18 C19 S12 111.8(8) . . ?
C18 C19 H19 124.1 . . ?
S12 C19 H19 124.1 . . ?
O30 C30 C31 136(3) . . ?
O30 C30 C36 101(3) . . ?
C31 C30 C36 123(3) . . ?
C30 C31 C32 125(3) . . ?
C30 C31 H31A 106.0 . . ?
C32 C31 H31A 106.0 . . ?
C30 C31 H31B 106.0 . . ?
C32 C31 H31B 106.0 . . ?
H31A C31 H31B 106.3 . . ?
C31 C32 C33 122(3) . . ?
C31 C32 H32A 106.8 . . ?
C33 C32 H32A 106.8 . . ?
C31 C32 H32B 106.8 . . ?
C33 C32 H32B 106.8 . . ?
H32A C32 H32B 106.6 . . ?
C34 C33 C32 113(2) . . ?
C34 C33 H33A 109.0 . . ?
C32 C33 H33A 109.0 . . ?
C34 C33 H33B 109.0 . . ?
C32 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C35 C34 C33 128(2) . . ?
C35 C34 H34A 105.2 . . ?
C33 C34 H34A 105.2 . . ?
C35 C34 H34B 105.2 . . ?
C33 C34 H34B 105.2 . . ?
H34A C34 H34B 105.9 . . ?
C34 C35 C36 116(2) . . ?
C34 C35 H35A 108.3 . . ?
C36 C35 H35A 108.3 . . ?
C34 C35 H35B 108.3 . . ?
C36 C35 H35B 108.3 . . ?
H35A C35 H35B 107.4 . . ?
C35 C36 C30 115(2) . . ?
C35 C36 H36A 108.5 . . ?
C30 C36 H36A 108.5 . . ?
C35 C36 H36B 108.5 . . ?
C30 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 167.4(7) . . . . ?
O12 S11 N12 C17 37.9(8) . . . . ?
C14 S11 N12 C17 -80.0(8) . . . . ?
N11 C11 C12 C13 178.2(9) . . . . ?
C16 C11 C12 C13 -1.3(15) . . . . ?
C11 C12 C13 C14 1.5(15) . . . . ?
C12 C13 C14 C15 -1.0(14) . . . . ?
C12 C13 C14 S11 179.2(8) . . . . ?
O11 S11 C14 C15 -129.3(8) . . . . ?
O12 S11 C14 C15 -1.9(8) . . . . ?
N12 S11 C14 C15 119.2(8) . . . . ?
O11 S11 C14 C13 50.4(8) . . . . ?
O12 S11 C14 C13 177.8(7) . . . . ?
N12 S11 C14 C13 -61.0(8) . . . . ?
C13 C14 C15 C16 0.3(13) . . . . ?
S11 C14 C15 C16 -179.9(7) . . . . ?
C14 C15 C16 C11 -0.2(15) . . . . ?
N11 C11 C16 C15 -178.9(10) . . . . ?
C12 C11 C16 C15 0.7(15) . . . . ?
S11 N12 C17 N13 172.6(6) . . . . ?
S11 N12 C17 S12 -7.5(12) . . . . ?
C18 N13 C17 N12 179.4(8) . . . . ?
C18 N13 C17 S12 -0.5(9) . . . . ?
C19 S12 C17 N12 179.7(9) . . . . ?
C19 S12 C17 N13 -0.3(7) . . . . ?
C17 N13 C18 C19 1.4(12) . . . . ?
N13 C18 C19 S12 -1.7(12) . . . . ?
C17 S12 C19 C18 1.1(8) . . . . ?
O30 C30 C31 C32 -163(4) . . . . ?
C36 C30 C31 C32 23(5) . . . . ?
C30 C31 C32 C33 43(5) . . . . ?
C31 C32 C33 C34 -64(4) . . . . ?
C32 C33 C34 C35 49(4) . . . . ?
C33 C34 C35 C36 -47(4) . . . . ?
C34 C35 C36 C30 62(3) . . . . ?
O30 C30 C36 C35 114(3) . . . . ?
C31 C30 C36 C35 -71(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H11 O12 0.88 2.01 2.888(11) 171.4 2 yes
N11 H10 O11 0.88 2.22 2.985(12) 145.1 2_655 yes
N13 H17 N12 0.88 1.99 2.855(12) 167.0 3_665 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20
_database_code_depnum_ccdc_archive 'CCDC 2120782'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 21o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_20                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.00 angstrom. Data were integrated to 0.92
angstrom resolution and all data were used in the refinement.
;
_vrf_PLAT029_20                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.726 Why?
RESPONSE: The data are uniformly >90% complete up to ca 1.0 angstrom. The 
final resolution shell 1.02-0.92 angstrom has very few reflections, which
leads to this relatively low fraction overall. The data could be truncated
or the _theta_full angle could be reduced to mitigate this warning, but
this will only raise alerts related to a low theta_full angle. The full
intensity statistics can be consulted in the CIF.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, cyclooctanone (2:1) solvate'
_chemical_name_common            'Sulfathiazole, cyclooctanone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C8 H14 O'
_chemical_formula_sum            'C26 H32 N6 O5 S4'
_chemical_formula_weight         636.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.783(1)
_cell_length_b                   14.728(4)
_cell_length_c                   23.800(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.46(1)
_cell_angle_gamma                90
_cell_volume                     3045.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      57.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    3.257
_shelx_estimated_absorpt_T_min   0.442
_shelx_estimated_absorpt_T_max   0.442
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3082
_diffrn_reflns_av_unetI/netI     0.1223
_diffrn_reflns_av_R_equivalents  0.1543
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.540
_diffrn_reflns_theta_max         57.184
_diffrn_reflns_theta_full        57.184
_diffrn_measured_fraction_theta_max 0.726
_diffrn_measured_fraction_theta_full 0.726
_diffrn_reflns_Laue_measured_fraction_max 0.726
_diffrn_reflns_Laue_measured_fraction_full 0.726
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_point_group_measured_fraction_full 0.726
_reflns_number_total             2999
_reflns_number_gt                1664
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  21o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 4.27      49     50     98.0     1.08     345.8   29.34  0.0612  0.0196
4.27 - 2.84     109    109    100.0     1.06     327.5   24.08  0.1354  0.0237
2.84 - 2.24     157    158     99.4     1.04     105.8   18.35  0.1775  0.0414
2.24 - 1.95     164    167     98.2     1.02      92.3   16.17  0.1591  0.0481
1.95 - 1.75     160    162     98.8     1.01      62.7   12.54  0.0974  0.0677
1.75 - 1.63     155    161     96.3     1.01      38.9    8.82  0.2037  0.1078
1.63 - 1.53     152    158     96.2     0.99      41.0    8.53  0.1653  0.1163
1.53 - 1.45     158    159     99.4     1.01      34.4    6.95  0.2130  0.1456
1.45 - 1.38     179    187     95.7     1.00      33.7    6.85  0.2542  0.1552
1.38 - 1.33     136    143     95.1     0.96      20.9    4.24  0.0596  0.2844
1.33 - 1.28     160    170     94.1     0.96      22.0    4.38  0.0892  0.2694
1.28 - 1.23     178    193     92.2     0.93      23.9    4.54  0.1829  0.2537
1.23 - 1.20     136    146     93.2     0.97      26.6    4.78  0.3179  0.2251
1.20 - 1.17     151    163     92.6     0.95      19.2    3.72  0.3671  0.3421
1.17 - 1.13     196    208     94.2     0.96      16.5    3.16  0.2479  0.3916
1.13 - 1.11     125    135     92.6     0.94      16.3    3.13  0.0534  0.3904
1.11 - 1.08     184    202     91.1     0.93      11.4    2.19  0.1634  0.6108
1.08 - 1.06     140    157     89.2     0.92      12.7    2.56  0.6195  0.5021
1.06 - 1.04     157    169     92.9     0.95      11.1    2.19  0.2152  0.5948
1.04 - 1.02     166    181     91.7     0.93       6.0    1.25  0.2661  1.1615
1.02 - 0.92     142   1151     12.3     0.12       5.0    1.10  0.3781  1.4538
#--------------------------------------------------------------------------------
1.02 - 0.92     142   1151     12.3     0.12       5.0    1.10  0.3781  1.4538
 Inf - 0.92    3154   4329     72.9     0.75      46.9    7.09  0.1544  0.1249
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The H atoms of the NH2 group are placed in-plane and allowed to ride.
This is an approximation.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1170P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2999
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.1863
_refine_ls_wR_factor_gt          0.1660
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_restrained_S_all      0.918
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.083

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S -0.0751(3) 0.68090(14) 0.92010(10) 0.0542(7) Uani 1 1 d . . . . .
S12 S -0.0971(3) 0.49883(16) 0.83883(10) 0.0691(8) Uani 1 1 d . . . . .
O11 O -0.0719(7) 0.7370(4) 0.9697(2) 0.0674(17) Uani 1 1 d . . . . .
O12 O -0.2049(6) 0.6887(4) 0.8760(3) 0.079(2) Uani 1 1 d . . . . .
N11 N 0.4863(8) 0.7200(4) 0.8148(3) 0.061(2) Uani 1 1 d . . . . .
H10 H 0.574008 0.728992 0.835351 0.092 Uiso 1 1 calc R U . . .
H11 H 0.480520 0.715056 0.778524 0.092 Uiso 1 1 calc R U . . .
N12 N -0.0593(7) 0.5781(4) 0.9456(3) 0.0447(17) Uani 1 1 d . . . . .
N13 N -0.0385(7) 0.4243(4) 0.9349(3) 0.0488(18) Uani 1 1 d . . . . .
H17 H -0.022975 0.415692 0.971076 0.073 Uiso 1 1 calc R U . . .
C11 C 0.3565(10) 0.7137(5) 0.8396(4) 0.043(2) Uani 1 1 d . . . . .
C12 C 0.3613(10) 0.7213(5) 0.8973(4) 0.050(2) Uani 1 1 d . . . . .
H12 H 0.455173 0.732718 0.919848 0.060 Uiso 1 1 calc R U . . .
C13 C 0.2308(11) 0.7124(5) 0.9229(4) 0.055(2) Uani 1 1 d . . . . .
H13 H 0.238000 0.713131 0.962291 0.066 Uiso 1 1 calc R U . . .
C14 C 0.0867(9) 0.7024(5) 0.8887(3) 0.040(2) Uani 1 1 d . . . . .
C15 C 0.0847(10) 0.6993(5) 0.8312(4) 0.046(2) Uani 1 1 d . . . . .
H15 H -0.009576 0.692873 0.807983 0.056 Uiso 1 1 calc R U . . .
C16 C 0.2125(10) 0.7052(6) 0.8065(3) 0.050(2) Uani 1 1 d . . . . .
H16 H 0.204773 0.703650 0.767169 0.060 Uiso 1 1 calc R U . . .
C17 C -0.0627(9) 0.5080(6) 0.9110(3) 0.046(2) Uani 1 1 d . . . . .
C18 C -0.0410(10) 0.3551(6) 0.8963(4) 0.066(3) Uani 1 1 d . . . . .
H18 H -0.025665 0.294570 0.906858 0.080 Uiso 1 1 calc R U . . .
C19 C -0.0675(11) 0.3823(6) 0.8424(4) 0.069(3) Uani 1 1 d . . . . .
H19 H -0.069783 0.344218 0.811085 0.083 Uiso 1 1 calc R U . . .
S21 S 0.4079(3) 0.60073(16) 0.66118(9) 0.0552(7) Uani 1 1 d . . . . .
S22 S 0.2755(4) 0.45500(17) 0.56244(11) 0.0862(10) Uani 1 1 d . . . . .
O21 O 0.4148(7) 0.6856(4) 0.6916(2) 0.0680(18) Uani 1 1 d . . . . .
O22 O 0.2941(6) 0.5368(4) 0.6746(2) 0.0681(18) Uani 1 1 d . . . . .
N21 N 1.0224(8) 0.4288(5) 0.7034(3) 0.075(2) Uani 1 1 d . . . . .
H20 H 1.103091 0.462218 0.704499 0.112 Uiso 1 1 calc R U . . .
H21 H 1.031812 0.371114 0.708487 0.112 Uiso 1 1 calc R U . . .
N22 N 0.3875(7) 0.6269(4) 0.5954(3) 0.0508(19) Uani 1 1 d . . . . .
N23 N 0.3297(8) 0.5874(5) 0.5015(3) 0.065(2) Uani 1 1 d . . . . .
H27 H 0.355405 0.640012 0.490392 0.097 Uiso 1 1 calc R U . . .
C21 C 0.8794(11) 0.4672(6) 0.6934(3) 0.053(2) Uani 1 1 d . . . . .
C22 C 0.8634(9) 0.5599(6) 0.6851(3) 0.057(3) Uani 1 1 d . . . . .
H22 H 0.950866 0.595718 0.685721 0.068 Uiso 1 1 calc R U . . .
C23 C 0.7207(10) 0.6000(6) 0.6759(3) 0.055(2) Uani 1 1 d . . . . .
H23 H 0.712995 0.662338 0.670072 0.066 Uiso 1 1 calc R U . . .
C24 C 0.5888(9) 0.5492(5) 0.6752(3) 0.047(2) Uani 1 1 d . . . . .
C25 C 0.6018(10) 0.4568(6) 0.6837(3) 0.053(2) Uani 1 1 d . . . . .
H25 H 0.513875 0.421600 0.683690 0.064 Uiso 1 1 calc R U . . .
C26 C 0.7462(10) 0.4160(6) 0.6923(3) 0.050(2) Uani 1 1 d . . . . .
H26 H 0.753724 0.353481 0.697431 0.060 Uiso 1 1 calc R U . . .
C27 C 0.3358(9) 0.5670(5) 0.5568(4) 0.053(2) Uani 1 1 d . . . . .
C28 C 0.2790(11) 0.5178(8) 0.4630(4) 0.084(3) Uani 1 1 d . . . . .
H28 H 0.269373 0.523156 0.423743 0.101 Uiso 1 1 calc R U . . .
C29 C 0.2466(14) 0.4433(7) 0.4904(4) 0.099(4) Uani 1 1 d . . . . .
H29 H 0.211596 0.389877 0.472083 0.119 Uiso 1 1 calc R U . . .
O30 O 0.6408(10) 0.2567(5) 0.9222(3) 0.115(3) Uani 1 1 d . . . . .
C30 C 0.5136(14) 0.2816(6) 0.8967(5) 0.083(4) Uani 1 1 d . . . . .
C31 C 0.4924(13) 0.2982(7) 0.8362(4) 0.097(4) Uani 1 1 d . . . . .
H31A H 0.454134 0.242852 0.816979 0.117 Uiso 1 1 calc R U . . .
H31B H 0.592389 0.310726 0.825178 0.117 Uiso 1 1 calc R U . . .
C32 C 0.3846(12) 0.3750(7) 0.8145(4) 0.087(3) Uani 1 1 d . . . . .
H32A H 0.362173 0.370699 0.773468 0.105 Uiso 1 1 calc R U . . .
H32B H 0.288477 0.366882 0.829406 0.105 Uiso 1 1 calc R U . . .
C33 C 0.4442(12) 0.4681(6) 0.8298(4) 0.084(3) Uani 1 1 d . . . . .
H33A H 0.366052 0.511890 0.814942 0.100 Uiso 1 1 calc R U . . .
H33B H 0.533646 0.478899 0.811197 0.100 Uiso 1 1 calc R U . . .
C34 C 0.4889(12) 0.4848(6) 0.8935(4) 0.077(3) Uani 1 1 d . . . . .
H34A H 0.579596 0.448928 0.907038 0.092 Uiso 1 1 calc R U . . .
H34B H 0.516370 0.548215 0.899393 0.092 Uiso 1 1 calc R U . . .
C35 C 0.3680(12) 0.4625(8) 0.9280(5) 0.087(3) Uani 1 1 d . . . . .
H35A H 0.270955 0.458553 0.902711 0.105 Uiso 1 1 calc R U . . .
H35B H 0.359657 0.512864 0.953648 0.105 Uiso 1 1 calc R U . . .
C36 C 0.3872(12) 0.3769(8) 0.9627(5) 0.095(4) Uani 1 1 d . . . . .
H36A H 0.482964 0.381196 0.988693 0.115 Uiso 1 1 calc R U . . .
H36B H 0.304350 0.373944 0.985500 0.115 Uiso 1 1 calc R U . . .
C37 C 0.3884(14) 0.2918(7) 0.9310(5) 0.099(4) Uani 1 1 d . . . . .
H37A H 0.291140 0.286404 0.906006 0.118 Uiso 1 1 calc R U . . .
H37B H 0.394463 0.241878 0.957815 0.118 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.436(5) . ?
S11 O11 1.438(6) . ?
S11 N12 1.630(6) . ?
S11 C14 1.730(8) . ?
S12 C17 1.705(8) . ?
S12 C19 1.737(9) . ?
N11 C11 1.362(9) . ?
N11 H10 0.8600 . ?
N11 H11 0.8600 . ?
N12 C17 1.319(9) . ?
N13 C17 1.361(9) . ?
N13 C18 1.371(10) . ?
N13 H17 0.8600 . ?
C11 C12 1.372(10) . ?
C11 C16 1.394(10) . ?
C12 C13 1.381(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.409(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(10) . ?
C15 C16 1.343(10) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.332(11) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
S21 O21 1.441(5) . ?
S21 O22 1.443(6) . ?
S21 N22 1.596(6) . ?
S21 C24 1.748(8) . ?
S22 C29 1.704(10) . ?
S22 C27 1.744(8) . ?
N21 C21 1.367(10) . ?
N21 H20 0.8600 . ?
N21 H21 0.8600 . ?
N22 C27 1.306(10) . ?
N23 C27 1.342(10) . ?
N23 C28 1.402(11) . ?
N23 H27 0.8600 . ?
C21 C22 1.384(11) . ?
C21 C26 1.389(11) . ?
C22 C23 1.374(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(10) . ?
C25 C26 1.391(10) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C28 C29 1.329(13) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
O30 C30 1.245(10) . ?
C30 C31 1.447(14) . ?
C30 C37 1.471(14) . ?
C31 C32 1.516(12) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.492(12) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.531(12) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.471(12) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.503(13) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.464(13) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 118.1(4) . . ?
O12 S11 N12 111.2(4) . . ?
O11 S11 N12 103.7(3) . . ?
O12 S11 C14 106.5(4) . . ?
O11 S11 C14 109.4(4) . . ?
N12 S11 C14 107.5(3) . . ?
C17 S12 C19 91.5(5) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 120.1(6) . . ?
C17 N13 C18 114.0(7) . . ?
C17 N13 H17 123.0 . . ?
C18 N13 H17 123.0 . . ?
N11 C11 C12 121.6(8) . . ?
N11 C11 C16 120.6(8) . . ?
C12 C11 C16 117.7(8) . . ?
C11 C12 C13 121.9(8) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 119.2(8) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 117.4(8) . . ?
C15 C14 S11 122.5(6) . . ?
C13 C14 S11 119.7(7) . . ?
C16 C15 C14 123.1(8) . . ?
C16 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C15 C16 C11 120.4(8) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N12 C17 N13 117.4(7) . . ?
N12 C17 S12 132.5(7) . . ?
N13 C17 S12 110.1(6) . . ?
C19 C18 N13 113.9(9) . . ?
C19 C18 H18 123.0 . . ?
N13 C18 H18 123.0 . . ?
C18 C19 S12 110.3(7) . . ?
C18 C19 H19 124.8 . . ?
S12 C19 H19 124.8 . . ?
O21 S21 O22 115.7(4) . . ?
O21 S21 N22 105.9(4) . . ?
O22 S21 N22 113.1(4) . . ?
O21 S21 C24 108.1(4) . . ?
O22 S21 C24 108.3(4) . . ?
N22 S21 C24 105.1(4) . . ?
C29 S22 C27 91.1(5) . . ?
C21 N21 H20 120.0 . . ?
C21 N21 H21 120.0 . . ?
H20 N21 H21 120.0 . . ?
C27 N22 S21 120.3(6) . . ?
C27 N23 C28 116.1(8) . . ?
C27 N23 H27 122.0 . . ?
C28 N23 H27 122.0 . . ?
N21 C21 C22 120.3(8) . . ?
N21 C21 C26 121.9(8) . . ?
C22 C21 C26 117.8(9) . . ?
C23 C22 C21 121.2(8) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 121.0(8) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C25 118.9(8) . . ?
C23 C24 S21 120.4(7) . . ?
C25 C24 S21 120.7(7) . . ?
C24 C25 C26 120.1(8) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 121.0(8) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
N22 C27 N23 119.9(7) . . ?
N22 C27 S22 131.5(7) . . ?
N23 C27 S22 108.6(7) . . ?
C29 C28 N23 110.7(9) . . ?
C29 C28 H28 124.7 . . ?
N23 C28 H28 124.7 . . ?
C28 C29 S22 113.5(8) . . ?
C28 C29 H29 123.2 . . ?
S22 C29 H29 123.2 . . ?
O30 C30 C31 120.7(13) . . ?
O30 C30 C37 116.7(12) . . ?
C31 C30 C37 122.6(10) . . ?
C30 C31 C32 116.6(9) . . ?
C30 C31 H31A 108.1 . . ?
C32 C31 H31A 108.1 . . ?
C30 C31 H31B 108.1 . . ?
C32 C31 H31B 108.1 . . ?
H31A C31 H31B 107.3 . . ?
C33 C32 C31 115.1(8) . . ?
C33 C32 H32A 108.5 . . ?
C31 C32 H32A 108.5 . . ?
C33 C32 H32B 108.5 . . ?
C31 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
C32 C33 C34 114.7(9) . . ?
C32 C33 H33A 108.6 . . ?
C34 C33 H33A 108.6 . . ?
C32 C33 H33B 108.6 . . ?
C34 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C35 C34 C33 114.6(9) . . ?
C35 C34 H34A 108.6 . . ?
C33 C34 H34A 108.6 . . ?
C35 C34 H34B 108.6 . . ?
C33 C34 H34B 108.6 . . ?
H34A C34 H34B 107.6 . . ?
C34 C35 C36 117.5(9) . . ?
C34 C35 H35A 107.9 . . ?
C36 C35 H35A 107.9 . . ?
C34 C35 H35B 107.9 . . ?
C36 C35 H35B 107.9 . . ?
H35A C35 H35B 107.2 . . ?
C37 C36 C35 116.3(9) . . ?
C37 C36 H36A 108.2 . . ?
C35 C36 H36A 108.2 . . ?
C37 C36 H36B 108.2 . . ?
C35 C36 H36B 108.2 . . ?
H36A C36 H36B 107.4 . . ?
C36 C37 C30 115.9(9) . . ?
C36 C37 H37A 108.3 . . ?
C30 C37 H37A 108.3 . . ?
C36 C37 H37B 108.3 . . ?
C30 C37 H37B 108.3 . . ?
H37A C37 H37B 107.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 50.0(7) . . . . ?
O11 S11 N12 C17 178.0(6) . . . . ?
C14 S11 N12 C17 -66.2(7) . . . . ?
N11 C11 C12 C13 -178.2(7) . . . . ?
C16 C11 C12 C13 6.0(11) . . . . ?
C11 C12 C13 C14 -5.0(12) . . . . ?
C12 C13 C14 C15 1.8(11) . . . . ?
C12 C13 C14 S11 174.1(6) . . . . ?
O12 S11 C14 C15 -17.1(7) . . . . ?
O11 S11 C14 C15 -145.9(6) . . . . ?
N12 S11 C14 C15 102.2(7) . . . . ?
O12 S11 C14 C13 170.9(6) . . . . ?
O11 S11 C14 C13 42.2(7) . . . . ?
N12 S11 C14 C13 -69.8(7) . . . . ?
C13 C14 C15 C16 0.2(11) . . . . ?
S11 C14 C15 C16 -171.9(6) . . . . ?
C14 C15 C16 C11 0.9(12) . . . . ?
N11 C11 C16 C15 -179.8(7) . . . . ?
C12 C11 C16 C15 -3.9(11) . . . . ?
S11 N12 C17 N13 175.7(5) . . . . ?
S11 N12 C17 S12 -6.2(11) . . . . ?
C18 N13 C17 N12 -178.9(7) . . . . ?
C18 N13 C17 S12 2.5(9) . . . . ?
C19 S12 C17 N12 178.7(9) . . . . ?
C19 S12 C17 N13 -3.1(6) . . . . ?
C17 N13 C18 C19 -0.3(11) . . . . ?
N13 C18 C19 S12 -2.0(11) . . . . ?
C17 S12 C19 C18 2.9(8) . . . . ?
O21 S21 N22 C27 -161.1(7) . . . . ?
O22 S21 N22 C27 -33.3(8) . . . . ?
C24 S21 N22 C27 84.6(7) . . . . ?
N21 C21 C22 C23 -178.9(7) . . . . ?
C26 C21 C22 C23 -0.2(12) . . . . ?
C21 C22 C23 C24 0.6(13) . . . . ?
C22 C23 C24 C25 -0.3(12) . . . . ?
C22 C23 C24 S21 -177.9(6) . . . . ?
O21 S21 C24 C23 -42.3(8) . . . . ?
O22 S21 C24 C23 -168.4(6) . . . . ?
N22 S21 C24 C23 70.5(7) . . . . ?
O21 S21 C24 C25 140.2(7) . . . . ?
O22 S21 C24 C25 14.1(8) . . . . ?
N22 S21 C24 C25 -107.1(7) . . . . ?
C23 C24 C25 C26 -0.5(12) . . . . ?
S21 C24 C25 C26 177.1(6) . . . . ?
N21 C21 C26 C25 178.1(7) . . . . ?
C22 C21 C26 C25 -0.6(12) . . . . ?
C24 C25 C26 C21 1.0(12) . . . . ?
S21 N22 C27 N23 -175.1(6) . . . . ?
S21 N22 C27 S22 1.6(12) . . . . ?
C28 N23 C27 N22 177.4(8) . . . . ?
C28 N23 C27 S22 0.0(10) . . . . ?
C29 S22 C27 N22 -176.8(9) . . . . ?
C29 S22 C27 N23 0.1(7) . . . . ?
C27 N23 C28 C29 -0.1(13) . . . . ?
N23 C28 C29 S22 0.2(13) . . . . ?
C27 S22 C29 C28 -0.2(10) . . . . ?
O30 C30 C31 C32 -144.7(10) . . . . ?
C37 C30 C31 C32 36.0(15) . . . . ?
C30 C31 C32 C33 70.9(14) . . . . ?
C31 C32 C33 C34 -56.8(13) . . . . ?
C32 C33 C34 C35 -52.8(12) . . . . ?
C33 C34 C35 C36 105.1(11) . . . . ?
C34 C35 C36 C37 -62.9(14) . . . . ?
C35 C36 C37 C30 61.9(14) . . . . ?
O30 C30 C37 C36 81.3(13) . . . . ?
C31 C30 C37 C36 -99.4(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.86 2.12 2.921(8) 154.1 1_655 yes
N11 H11 O21 0.86 2.11 2.950(9) 165.6 . yes
N13 H17 S11 0.86 2.97 3.780(7) 157.8 3_567 yes
N13 H17 N12 0.86 2.01 2.845(9) 163.9 3_567 yes
N21 H20 O22 0.86 2.21 3.029(9) 159.4 1_655 yes
N21 H21 N11 0.86 2.29 3.104(9) 157.2 2_646 yes
N23 H27 O11 0.86 2.01 2.864(9) 175.5 4_675 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_15
_database_code_depnum_ccdc_archive 'CCDC 2120777'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 16o
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole (+/-)2-methylcyclopentanone (1:1) solvate'
_chemical_name_common            
'Sulfathiazole, 2-methylcyclopentan-1-one solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C6 H10 O'
_chemical_formula_sum            'C15 H19 N3 O3 S2'
_chemical_formula_weight         353.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.550(2)
_cell_length_b                   21.491(4)
_cell_length_c                   9.215(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.27(3)
_cell_angle_gamma                90
_cell_volume                     1693.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13217
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.332
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13217
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.405
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.024
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2980
_reflns_number_gt                2054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#===============================================================================
INTENSITY STATISTICS FOR DATASET # 1  16o.hkl
#===============================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#===============================================================================
 Inf - 3.54      47     50     94.0     4.10     164.9   31.15  0.0218  0.0251
3.54 - 2.32     107    107    100.0     4.74      74.0   30.59  0.0251  0.0248
2.32 - 1.83     154    154    100.0     4.81      38.3   27.01  0.0347  0.0275
1.83 - 1.60     155    155    100.0     4.83      27.9   20.54  0.0385  0.0301
1.60 - 1.44     158    158    100.0     4.78      24.5   18.47  0.0430  0.0350
1.44 - 1.34     160    160    100.0     4.86      16.9   14.84  0.0568  0.0429
1.34 - 1.26     146    146    100.0     4.73      15.8   13.46  0.0621  0.0495
1.26 - 1.20     153    153    100.0     4.91      15.5   13.08  0.0724  0.0506
1.20 - 1.14     163    163    100.0     4.74      16.9   13.18  0.0705  0.0552
1.14 - 1.10     156    156    100.0     4.68      10.7   10.47  0.0956  0.0707
1.10 - 1.06     143    143    100.0     4.71      12.4   10.37  0.0882  0.0679
1.06 - 1.03     144    144    100.0     4.88       8.2    8.34  0.1209  0.0881
1.03 - 1.00     162    162    100.0     4.63       6.4    6.32  0.1470  0.1153
1.00 - 0.97     162    162    100.0     4.56       5.9    6.30  0.1738  0.1250
0.97 - 0.95     135    135    100.0     4.30       4.8    5.14  0.2007  0.1515
0.95 - 0.92     207    207    100.0     4.26       4.6    4.71  0.1962  0.1678
0.92 - 0.90     165    165    100.0     3.79       4.1    3.68  0.2243  0.2077
0.90 - 0.88     174    174    100.0     3.66       4.0    3.34  0.2827  0.2301
0.88 - 0.87     102    104     98.1     3.21       3.1    2.95  0.3096  0.2951
0.87 - 0.85     175    180     97.2     3.09       2.8    2.46  0.3077  0.3581
0.85 - 0.84     106    111     95.5     2.61       3.7    2.71  0.2676  0.3232
#-------------------------------------------------------------------------------
0.94 - 0.84     860    872     98.6     3.48       3.7    3.29  0.2540  0.2525
 Inf - 0.84    3074   3089     99.5     4.35      16.5   10.97  0.0635  0.0563
#===============================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0721P)²+0.4070P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2980
_refine_ls_number_parameters     272
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.061

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.49959(8) 0.85584(3) 0.62874(7) 0.0283(2) Uani 1 1 d . . . . .
S12 S 0.56674(10) 0.85377(4) 0.27646(8) 0.0417(3) Uani 1 1 d . . . . .
O11 O 0.4960(2) 0.87745(10) 0.77690(19) 0.0349(5) Uani 1 1 d . . . . .
O12 O 0.6217(2) 0.81292(10) 0.5893(2) 0.0351(5) Uani 1 1 d . . . . .
N11 N -0.1051(3) 0.73583(15) 0.4951(3) 0.0448(7) Uani 1 1 d D . . . .
H10 H -0.114(3) 0.7090(14) 0.430(3) 0.047(10) Uiso 1 1 d D . . . .
H11 H -0.190(3) 0.7523(15) 0.518(3) 0.062(12) Uiso 1 1 d D . . . .
N12 N 0.5088(3) 0.91824(11) 0.5329(2) 0.0286(6) Uani 1 1 d . . . . .
N13 N 0.5494(3) 0.96967(12) 0.3162(2) 0.0307(6) Uani 1 1 d . . . . .
H17 H 0.539714 1.006453 0.357105 0.046 Uiso 1 1 calc R U . . .
C11 C 0.0339(3) 0.76404(15) 0.5258(3) 0.0336(7) Uani 1 1 d . . . . .
C12 C 0.0428(3) 0.81278(15) 0.6263(3) 0.0364(7) Uani 1 1 d . . . . .
H12 H -0.049700 0.826797 0.672790 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1840(3) 0.84074(14) 0.6587(3) 0.0333(7) Uani 1 1 d . . . . .
H13 H 0.188416 0.873990 0.726541 0.040 Uiso 1 1 calc R U . . .
C14 C 0.3207(3) 0.81995(14) 0.5914(3) 0.0282(7) Uani 1 1 d . . . . .
C15 C 0.3130(3) 0.77120(14) 0.4927(3) 0.0306(7) Uani 1 1 d . . . . .
H15 H 0.405828 0.756744 0.447637 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1717(3) 0.74359(14) 0.4596(3) 0.0328(7) Uani 1 1 d . . . . .
H16 H 0.167852 0.710459 0.391424 0.039 Uiso 1 1 calc R U . . .
C17 C 0.5395(3) 0.91677(13) 0.3911(3) 0.0278(7) Uani 1 1 d . . . . .
C18 C 0.5761(3) 0.96233(16) 0.1690(3) 0.0358(7) Uani 1 1 d . . . . .
H18 H 0.586598 0.996125 0.103327 0.043 Uiso 1 1 calc R U . . .
C19 C 0.5856(4) 0.90337(16) 0.1298(3) 0.0420(8) Uani 1 1 d . . . . .
H19 H 0.600821 0.889830 0.032795 0.050 Uiso 1 1 calc R U . . .
O1 O 0.1782(4) 0.9544(2) -0.0278(5) 0.1180(15) Uani 0.556(8) 1 d D . P A 1
C1 C 0.1544(12) 0.9567(5) 0.1065(10) 0.099(4) Uani 0.556(8) 1 d D . P A 1
C2 C 0.0898(14) 0.9076(4) 0.2088(10) 0.103(4) Uani 0.556(8) 1 d D . P A 1
H2 H 0.187408 0.891561 0.255803 0.123 Uiso 0.556(8) 1 calc R U P A 1
C3 C 0.0156(13) 0.9411(4) 0.3295(10) 0.090(3) Uani 0.556(8) 1 d D . P A 1
H3A H 0.024555 0.916886 0.420546 0.108 Uiso 0.556(8) 1 calc R U P A 1
H3B H -0.096554 0.948497 0.308540 0.108 Uiso 0.556(8) 1 calc R U P A 1
C4 C 0.1035(13) 1.0030(5) 0.3432(11) 0.091(3) Uani 0.556(8) 1 d D . P A 1
H4A H 0.033133 1.036522 0.377388 0.109 Uiso 0.556(8) 1 calc R U P A 1
H4B H 0.192899 0.999322 0.411302 0.109 Uiso 0.556(8) 1 calc R U P A 1
C5 C 0.159(3) 1.0158(6) 0.1901(14) 0.093(6) Uani 0.556(8) 1 d D . P A 1
H5A H 0.090919 1.047165 0.143281 0.112 Uiso 0.556(8) 1 calc R U P A 1
H5B H 0.267329 1.032282 0.192567 0.112 Uiso 0.556(8) 1 calc R U P A 1
C6 C 0.0266(19) 0.8516(6) 0.1435(14) 0.089(5) Uani 0.556(8) 1 d D . P A 1
H6A H 0.095680 0.837713 0.065383 0.133 Uiso 0.556(8) 1 calc R U P A 1
H6B H 0.018821 0.818951 0.217231 0.133 Uiso 0.556(8) 1 calc R U P A 1
H6C H -0.077602 0.860378 0.103576 0.133 Uiso 0.556(8) 1 calc R U P A 1
O1' O 0.1782(4) 0.9544(2) -0.0278(5) 0.1180(15) Uani 0.444(8) 1 d D . P A 2
C1' C 0.1152(9) 0.9271(4) 0.0615(8) 0.051(3) Uani 0.444(8) 1 d D U P A 2
C2' C 0.1419(11) 0.9440(4) 0.2192(10) 0.065(3) Uani 0.444(8) 1 d D U P A 2
H2' H 0.245845 0.926076 0.246607 0.077 Uiso 0.444(8) 1 calc R U P A 2
C3' C 0.0222(13) 0.9044(4) 0.2903(10) 0.056(3) Uani 0.444(8) 1 d D U P A 2
H3A' H -0.078558 0.926829 0.296830 0.068 Uiso 0.444(8) 1 calc R U P A 2
H3B' H 0.056515 0.892927 0.389560 0.068 Uiso 0.444(8) 1 calc R U P A 2
C4' C 0.0041(18) 0.8460(5) 0.1963(13) 0.048(3) Uani 0.444(8) 1 d D U P A 2
H4A' H 0.086007 0.814956 0.219699 0.057 Uiso 0.444(8) 1 calc R U P A 2
H4B' H -0.099955 0.826751 0.209856 0.057 Uiso 0.444(8) 1 calc R U P A 2
C5' C 0.0225(11) 0.8702(4) 0.0433(10) 0.053(2) Uani 0.444(8) 1 d D U P A 2
H5A' H 0.077946 0.839706 -0.018288 0.063 Uiso 0.444(8) 1 calc R U P A 2
H5B' H -0.080579 0.879559 -0.001010 0.063 Uiso 0.444(8) 1 calc R U P A 2
C6' C 0.151(3) 1.0112(6) 0.2508(19) 0.068(5) Uani 0.444(8) 1 d D U P A 2
H6A' H 0.236250 1.029730 0.194615 0.102 Uiso 0.444(8) 1 calc R U P A 2
H6B' H 0.051996 1.031109 0.224207 0.102 Uiso 0.444(8) 1 calc R U P A 2
H6C' H 0.171303 1.017280 0.354598 0.102 Uiso 0.444(8) 1 calc R U P A 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.441(2) . ?
S11 O11 1.443(2) . ?
S11 N12 1.608(2) . ?
S11 C14 1.746(3) . ?
S12 C19 1.729(3) . ?
S12 C17 1.734(3) . ?
N11 C11 1.363(4) . ?
N11 H10 0.84(2) . ?
N11 H11 0.84(2) . ?
N12 C17 1.335(4) . ?
N13 C17 1.333(4) . ?
N13 C18 1.385(3) . ?
N13 H17 0.8800 . ?
C11 C16 1.400(4) . ?
C11 C12 1.400(4) . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(4) . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.320(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O1 C1 1.256(8) . ?
C1 C5 1.486(12) . ?
C1 C2 1.520(10) . ?
C2 C6 1.449(13) . ?
C2 C3 1.472(10) . ?
C2 H2 1.0000 . ?
C3 C4 1.533(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.516(12) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O1' C1' 1.147(7) . ?
C1' C5' 1.466(10) . ?
C1' C2' 1.514(9) . ?
C2' C6' 1.475(13) . ?
C2' C3' 1.486(10) . ?
C2' H2' 1.0000 . ?
C3' C4' 1.532(13) . ?
C3' H3A' 0.9900 . ?
C3' H3B' 0.9900 . ?
C4' C5' 1.512(11) . ?
C4' H4A' 0.9900 . ?
C4' H4B' 0.9900 . ?
C5' H5A' 0.9900 . ?
C5' H5B' 0.9900 . ?
C6' H6A' 0.9800 . ?
C6' H6B' 0.9800 . ?
C6' H6C' 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 117.61(12) . . ?
O12 S11 N12 110.99(12) . . ?
O11 S11 N12 104.65(12) . . ?
O12 S11 C14 107.60(13) . . ?
O11 S11 C14 107.82(12) . . ?
N12 S11 C14 107.77(13) . . ?
C19 S12 C17 90.44(15) . . ?
C11 N11 H10 122(2) . . ?
C11 N11 H11 121(2) . . ?
H10 N11 H11 113.3(18) . . ?
C17 N12 S11 121.9(2) . . ?
C17 N13 C18 114.9(3) . . ?
C17 N13 H17 122.6 . . ?
C18 N13 H17 122.6 . . ?
N11 C11 C16 120.4(3) . . ?
N11 C11 C12 120.9(3) . . ?
C16 C11 C12 118.7(3) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 S11 120.1(2) . . ?
C13 C14 S11 120.3(2) . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N13 C17 N12 120.0(3) . . ?
N13 C17 S12 110.0(2) . . ?
N12 C17 S12 130.0(2) . . ?
C19 C18 N13 112.8(3) . . ?
C19 C18 H18 123.6 . . ?
N13 C18 H18 123.6 . . ?
C18 C19 S12 111.8(2) . . ?
C18 C19 H19 124.1 . . ?
S12 C19 H19 124.1 . . ?
O1 C1 C5 122.6(9) . . ?
O1 C1 C2 130.2(7) . . ?
C5 C1 C2 106.3(7) . . ?
C6 C2 C3 124.0(10) . . ?
C6 C2 C1 117.1(8) . . ?
C3 C2 C1 106.8(7) . . ?
C6 C2 H2 101.7 . . ?
C3 C2 H2 101.7 . . ?
C1 C2 H2 101.7 . . ?
C2 C3 C4 105.9(7) . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C3 103.7(8) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C1 C5 C4 108.7(9) . . ?
C1 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
C1 C5 H5B 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.3 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1' C1' C5' 126.9(8) . . ?
O1' C1' C2' 119.8(7) . . ?
C5' C1' C2' 112.9(6) . . ?
C6' C2' C3' 120.7(10) . . ?
C6' C2' C1' 115.6(10) . . ?
C3' C2' C1' 100.7(6) . . ?
C6' C2' H2' 106.3 . . ?
C3' C2' H2' 106.3 . . ?
C1' C2' H2' 106.3 . . ?
C2' C3' C4' 106.7(7) . . ?
C2' C3' H3A' 110.4 . . ?
C4' C3' H3A' 110.4 . . ?
C2' C3' H3B' 110.4 . . ?
C4' C3' H3B' 110.4 . . ?
H3A' C3' H3B' 108.6 . . ?
C5' C4' C3' 103.6(8) . . ?
C5' C4' H4A' 111.0 . . ?
C3' C4' H4A' 111.0 . . ?
C5' C4' H4B' 111.0 . . ?
C3' C4' H4B' 111.0 . . ?
H4A' C4' H4B' 109.0 . . ?
C1' C5' C4' 103.8(7) . . ?
C1' C5' H5A' 111.0 . . ?
C4' C5' H5A' 111.0 . . ?
C1' C5' H5B' 111.0 . . ?
C4' C5' H5B' 111.0 . . ?
H5A' C5' H5B' 109.0 . . ?
C2' C6' H6A' 109.5 . . ?
C2' C6' H6B' 109.5 . . ?
H6A' C6' H6B' 109.5 . . ?
C2' C6' H6C' 109.5 . . ?
H6A' C6' H6C' 109.5 . . ?
H6B' C6' H6C' 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 41.1(3) . . . . ?
O11 S11 N12 C17 168.9(2) . . . . ?
C14 S11 N12 C17 -76.5(2) . . . . ?
N11 C11 C12 C13 179.1(3) . . . . ?
C16 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C12 C13 C14 S11 178.8(2) . . . . ?
O12 S11 C14 C15 -21.5(3) . . . . ?
O11 S11 C14 C15 -149.3(2) . . . . ?
N12 S11 C14 C15 98.3(2) . . . . ?
O12 S11 C14 C13 159.6(2) . . . . ?
O11 S11 C14 C13 31.8(3) . . . . ?
N12 S11 C14 C13 -80.7(2) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
S11 C14 C15 C16 -178.3(2) . . . . ?
C14 C15 C16 C11 -0.4(4) . . . . ?
N11 C11 C16 C15 -178.6(3) . . . . ?
C12 C11 C16 C15 -0.2(4) . . . . ?
C18 N13 C17 N12 -177.8(2) . . . . ?
C18 N13 C17 S12 0.8(3) . . . . ?
S11 N12 C17 N13 -178.5(2) . . . . ?
S11 N12 C17 S12 3.2(4) . . . . ?
C19 S12 C17 N13 -1.4(2) . . . . ?
C19 S12 C17 N12 176.9(3) . . . . ?
C17 N13 C18 C19 0.6(4) . . . . ?
N13 C18 C19 S12 -1.7(4) . . . . ?
C17 S12 C19 C18 1.8(3) . . . . ?
O1 C1 C2 C6 -9(2) . . . . ?
C5 C1 C2 C6 160.7(14) . . . . ?
O1 C1 C2 C3 -152.7(12) . . . . ?
C5 C1 C2 C3 16.7(16) . . . . ?
C6 C2 C3 C4 -169.3(12) . . . . ?
C1 C2 C3 C4 -28.4(12) . . . . ?
C2 C3 C4 C5 28.8(15) . . . . ?
O1 C1 C5 C4 172.2(12) . . . . ?
C2 C1 C5 C4 2(2) . . . . ?
C3 C4 C5 C1 -18.6(19) . . . . ?
O1' C1' C2' C6' 40.2(16) . . . . ?
C5' C1' C2' C6' -147.3(13) . . . . ?
O1' C1' C2' C3' 171.9(9) . . . . ?
C5' C1' C2' C3' -15.6(10) . . . . ?
C6' C2' C3' C4' 159.5(13) . . . . ?
C1' C2' C3' C4' 31.0(11) . . . . ?
C2' C3' C4' C5' -36.2(13) . . . . ?
O1' C1' C5' C4' 165.7(11) . . . . ?
C2' C1' C5' C4' -6.2(12) . . . . ?
C3' C4' C5' C1' 24.8(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.84(2) 2.52(2) 3.276(4) 152(2) 4_575 yes
N11 H11 O12 0.84(2) 2.17(2) 2.996(4) 167(3) 1_455 yes
N13 H17 S11 0.88 2.98 3.808(3) 157.1 3_676 yes
N13 H17 N12 0.88 1.96 2.827(3) 170.6 3_676 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14
_database_code_depnum_ccdc_archive 'CCDC 2120776'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 15o
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 4-methyloxetan-2-one (1:1) solvate'
_chemical_name_common            'Sulfathiazole, beta-butyrolactone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H6 O2'
_chemical_formula_sum            'C13 H15 N3 O4 S2'
_chemical_formula_weight         341.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.606(2)
_cell_length_b                   21.643(4)
_cell_length_c                   8.735(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.76(3)
_cell_angle_gamma                90
_cell_volume                     1608.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9351
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      30.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.351
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9351
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         30.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4773
_reflns_number_gt                3274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#===============================================================================
INTENSITY STATISTICS FOR DATASET # 1  15o.hkl
#===============================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#===============================================================================
 Inf - 2.81      75     84     89.3     1.63     403.4   47.76  0.0118  0.0181
2.81 - 1.94     172    172    100.0     1.91     178.1   38.75  0.0114  0.0196
1.94 - 1.53     249    249    100.0     1.93     104.5   31.29  0.0171  0.0224
1.53 - 1.34     243    243    100.0     1.93      75.5   25.89  0.0177  0.0266
1.34 - 1.21     247    247    100.0     1.94      55.6   21.06  0.0197  0.0295
1.21 - 1.12     261    261    100.0     1.95      51.5   20.90  0.0253  0.0328
1.12 - 1.05     266    266    100.0     1.94      39.3   17.46  0.0307  0.0406
1.05 - 1.00     228    228    100.0     1.96      27.3   14.58  0.0418  0.0495
1.00 - 0.96     221    221    100.0     1.95      23.6   12.39  0.0526  0.0580
0.96 - 0.92     281    281    100.0     1.93      16.7    9.42  0.0721  0.0787
0.92 - 0.89     224    225     99.6     1.96      17.7    9.29  0.0809  0.0797
0.89 - 0.86     253    255     99.2     1.92      14.6    7.69  0.1092  0.1006
0.86 - 0.83     309    312     99.0     1.93      11.0    6.32  0.1141  0.1268
0.83 - 0.81     223    229     97.4     1.89      12.3    6.19  0.1186  0.1274
0.81 - 0.79     230    240     95.8     1.88      10.1    5.73  0.1620  0.1530
0.79 - 0.77     278    289     96.2     1.87       9.9    4.98  0.1595  0.1672
0.77 - 0.75     295    313     94.2     1.83       7.6    3.90  0.2144  0.2230
0.75 - 0.74     156    168     92.9     1.82       6.3    3.27  0.2547  0.2828
0.74 - 0.72     324    353     91.8     1.76       6.7    3.15  0.3011  0.2790
0.72 - 0.71     173    191     90.6     1.75       7.2    3.41  0.3525  0.2734
0.71 - 0.69     192    409     46.9     0.88       5.7    2.65  0.3431  0.3547
#-------------------------------------------------------------------------------
0.79 - 0.69    1418   1723     82.3     1.59       7.4    3.64  0.2513  0.2453
 Inf - 0.69    4900   5236     93.6     1.81      37.9   12.69  0.0425  0.0478
#===============================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+1.0887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4773
_refine_ls_number_parameters     221
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.065

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.47993(6) 0.14476(2) 0.39504(6) 0.02647(14) Uani 1 1 d . . . . .
S12 S 0.59840(8) 0.13743(3) 0.77194(7) 0.03717(16) Uani 1 1 d . . . . .
O11 O 0.4546(2) 0.12661(7) 0.23406(17) 0.0347(4) Uani 1 1 d . . . . .
O12 O 0.60871(18) 0.18628(7) 0.4458(2) 0.0361(4) Uani 1 1 d . . . . .
N11 N -0.1035(2) 0.25903(11) 0.5363(3) 0.0477(6) Uani 1 1 d D . . . .
H10 H -0.107(3) 0.2898(11) 0.597(3) 0.059(9) Uiso 1 1 d D . . . .
H11 H -0.194(2) 0.2440(11) 0.502(3) 0.042(7) Uiso 1 1 d D . . . .
N12 N 0.4995(2) 0.08031(8) 0.4875(2) 0.0268(4) Uani 1 1 d . . . . .
N13 N 0.5666(2) 0.02363(8) 0.7117(2) 0.0280(4) Uani 1 1 d . . . . .
H17 H 0.547766 -0.011670 0.662398 0.042 Uiso 1 1 calc R U . . .
C11 C 0.0309(3) 0.23326(10) 0.5042(3) 0.0296(4) Uani 1 1 d . . . . .
C12 C 0.0261(3) 0.18221(10) 0.4032(2) 0.0298(5) Uani 1 1 d . . . . .
H12 H -0.072511 0.165700 0.357996 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1622(3) 0.15607(10) 0.3696(2) 0.0277(4) Uani 1 1 d . . . . .
H13 H 0.157350 0.121708 0.301370 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3082(2) 0.17997(9) 0.4356(2) 0.0247(4) Uani 1 1 d . . . . .
C15 C 0.3152(2) 0.23006(9) 0.5367(2) 0.0262(4) Uani 1 1 d . . . . .
H15 H 0.414287 0.246152 0.582127 0.031 Uiso 1 1 calc R U . . .
C16 C 0.1785(3) 0.25632(10) 0.5708(2) 0.0283(4) Uani 1 1 d . . . . .
H16 H 0.184094 0.290367 0.640041 0.034 Uiso 1 1 calc R U . . .
C17 C 0.5491(2) 0.07800(9) 0.6391(2) 0.0257(4) Uani 1 1 d . . . . .
C18 C 0.6161(3) 0.02650(11) 0.8693(2) 0.0344(5) Uani 1 1 d . . . . .
H18 H 0.633050 -0.008969 0.933783 0.041 Uiso 1 1 calc R U . . .
C19 C 0.6377(3) 0.08418(12) 0.9220(3) 0.0399(6) Uani 1 1 d . . . . .
H19 H 0.670309 0.094788 1.027506 0.048 Uiso 1 1 calc R U . . .
O30 O 0.2184(3) 0.04600(11) 0.8215(3) 0.0533(8) Uani 0.789(5) 1 d D . P A 1
O31 O 0.1274(4) -0.04706(12) 0.7342(3) 0.1023(11) Uani 0.789(5) 1 d D . P A 1
C30 C 0.1126(4) 0.00678(14) 0.7438(3) 0.0550(8) Uani 0.789(5) 1 d D . P A 1
C31 C -0.0007(4) 0.05768(16) 0.6812(4) 0.0456(9) Uani 0.789(5) 1 d D . P A 1
H31A H -0.103600 0.056155 0.718507 0.055 Uiso 0.789(5) 1 calc R U P A 1
H31B H -0.013136 0.063198 0.567459 0.055 Uiso 0.789(5) 1 calc R U P A 1
C32 C 0.1208(4) 0.10127(15) 0.7741(4) 0.0421(8) Uani 0.789(5) 1 d D . P A 1
H32A H 0.171340 0.129452 0.705529 0.051 Uiso 0.789(5) 1 calc R U P A 1
C33 C 0.0740(5) 0.13384(17) 0.9076(5) 0.0791(11) Uani 0.789(5) 1 d D . P A 1
H33A H 0.009942 0.169899 0.871272 0.119 Uiso 0.789(5) 1 calc R U P A 1
H33B H 0.012711 0.105941 0.963589 0.119 Uiso 0.789(5) 1 calc R U P A 1
H33C H 0.168176 0.147396 0.976971 0.119 Uiso 0.789(5) 1 calc R U P A 1
O30' O 0.136(3) 0.0633(4) 0.697(3) 0.213(13) Uiso 0.211(5) 1 d D . P A 2
O31' O 0.1274(4) -0.04706(12) 0.7342(3) 0.1023(11) Uani 0.211(5) 1 d D . P A 2
C30' C 0.1126(4) 0.00678(14) 0.7438(3) 0.0550(8) Uani 0.211(5) 1 d D . P A 2
C31' C -0.0026(17) 0.0247(5) 0.8509(17) 0.075(5) Uiso 0.211(5) 1 d D . P A 2
H31C H 0.037839 0.019882 0.962616 0.090 Uiso 0.211(5) 1 calc R U P A 2
H31D H -0.108930 0.006712 0.823415 0.090 Uiso 0.211(5) 1 calc R U P A 2
C32' C 0.0164(16) 0.0897(4) 0.7864(15) 0.077(5) Uiso 0.211(5) 1 d D . P A 2
H32' H -0.080405 0.104345 0.718112 0.093 Uiso 0.211(5) 1 calc R U P A 2
C33' C 0.0740(5) 0.13384(17) 0.9076(5) 0.0791(11) Uani 0.211(5) 1 d D . P A 2
H33D H -0.013663 0.147978 0.958291 0.119 Uiso 0.211(5) 1 calc R U P A 2
H33E H 0.153437 0.113995 0.984233 0.119 Uiso 0.211(5) 1 calc R U P A 2
H33F H 0.120957 0.169283 0.861889 0.119 Uiso 0.211(5) 1 calc R U P A 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.4432(16) . ?
S11 O11 1.4441(16) . ?
S11 N12 1.6078(18) . ?
S11 C14 1.746(2) . ?
S12 C19 1.739(2) . ?
S12 C17 1.741(2) . ?
N11 C11 1.352(3) . ?
N11 H10 0.85(2) . ?
N11 H11 0.86(2) . ?
N12 C17 1.329(3) . ?
N13 C17 1.334(3) . ?
N13 C18 1.379(3) . ?
N13 H17 0.8800 . ?
C11 C16 1.405(3) . ?
C11 C12 1.410(3) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.334(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C30 1.350(4) . ?
O30 C32 1.484(4) . ?
O31 C30 1.177(3) . ?
C30 C31 1.517(4) . ?
C31 C32 1.544(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.470(5) . ?
C32 H32A 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
O30' C30' 1.314(9) . ?
O30' C32' 1.494(10) . ?
O31' C30' 1.177(3) . ?
C30' C31' 1.513(9) . ?
C30' C32' 2.033(8) . ?
C31' C32' 1.533(10) . ?
C31' H31C 0.9900 . ?
C31' H31D 0.9900 . ?
C32' C33' 1.457(10) . ?
C32' H32' 1.0000 . ?
C33' H33D 0.9800 . ?
C33' H33E 0.9800 . ?
C33' H33F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 117.61(10) . . ?
O12 S11 N12 111.66(10) . . ?
O11 S11 N12 104.01(9) . . ?
O12 S11 C14 107.45(10) . . ?
O11 S11 C14 108.02(10) . . ?
N12 S11 C14 107.69(10) . . ?
C19 S12 C17 90.70(11) . . ?
C11 N11 H10 124.0(17) . . ?
C11 N11 H11 122.5(16) . . ?
H10 N11 H11 113.3(16) . . ?
C17 N12 S11 121.77(15) . . ?
C17 N13 C18 115.47(18) . . ?
C17 N13 H17 122.3 . . ?
C18 N13 H17 122.3 . . ?
N11 C11 C16 121.0(2) . . ?
N11 C11 C12 120.6(2) . . ?
C16 C11 C12 118.4(2) . . ?
C13 C12 C11 120.81(19) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.10(19) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.89(19) . . ?
C15 C14 S11 120.77(16) . . ?
C13 C14 S11 119.31(15) . . ?
C16 C15 C14 120.07(19) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.73(19) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N12 C17 N13 120.18(18) . . ?
N12 C17 S12 130.16(16) . . ?
N13 C17 S12 109.66(15) . . ?
C19 C18 N13 113.1(2) . . ?
C19 C18 H18 123.5 . . ?
N13 C18 H18 123.5 . . ?
C18 C19 S12 111.08(17) . . ?
C18 C19 H19 124.5 . . ?
S12 C19 H19 124.5 . . ?
C30 O30 C32 93.2(2) . . ?
O31 C30 O30 125.9(3) . . ?
O31 C30 C31 139.8(3) . . ?
O30 C30 C31 94.1(2) . . ?
C30 C31 C32 84.7(2) . . ?
C30 C31 H31A 114.5 . . ?
C32 C31 H31A 114.5 . . ?
C30 C31 H31B 114.5 . . ?
C32 C31 H31B 114.5 . . ?
H31A C31 H31B 111.6 . . ?
C33 C32 O30 112.1(3) . . ?
C33 C32 C31 117.7(3) . . ?
O30 C32 C31 87.9(2) . . ?
C33 C32 H32A 112.3 . . ?
O30 C32 H32A 112.3 . . ?
C31 C32 H32A 112.3 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30' O30' C32' 92.5(7) . . ?
O31' C30' O30' 151.2(7) . . ?
O31' C30' C31' 112.7(5) . . ?
O30' C30' C31' 95.6(6) . . ?
O31' C30' C32' 159.8(5) . . ?
O30' C30' C32' 47.2(5) . . ?
C31' C30' C32' 48.5(4) . . ?
C30' C31' C32' 83.7(5) . . ?
C30' C31' H31C 114.7 . . ?
C32' C31' H31C 114.7 . . ?
C30' C31' H31D 114.7 . . ?
C32' C31' H31D 114.7 . . ?
H31C C31' H31D 111.8 . . ?
C33' C32' O30' 116.5(13) . . ?
C33' C32' C31' 112.2(10) . . ?
O30' C32' C31' 87.8(6) . . ?
C33' C32' C30' 127.5(7) . . ?
O30' C32' C30' 40.2(4) . . ?
C31' C32' C30' 47.7(4) . . ?
C33' C32' H32' 112.7 . . ?
O30' C32' H32' 112.7 . . ?
C31' C32' H32' 112.7 . . ?
C30' C32' H32' 119.8 . . ?
C32' C33' H33D 109.5 . . ?
C32' C33' H33E 109.5 . . ?
H33D C33' H33E 109.5 . . ?
C32' C33' H33F 109.5 . . ?
H33D C33' H33F 109.5 . . ?
H33E C33' H33F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 41.5(2) . . . . ?
O11 S11 N12 C17 169.29(17) . . . . ?
C14 S11 N12 C17 -76.24(19) . . . . ?
N11 C11 C12 C13 179.6(2) . . . . ?
C16 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C12 C13 C14 S11 178.38(16) . . . . ?
O12 S11 C14 C15 -15.55(19) . . . . ?
O11 S11 C14 C15 -143.36(17) . . . . ?
N12 S11 C14 C15 104.87(17) . . . . ?
O12 S11 C14 C13 166.62(16) . . . . ?
O11 S11 C14 C13 38.81(19) . . . . ?
N12 S11 C14 C13 -72.96(18) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
S11 C14 C15 C16 -178.25(16) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
N11 C11 C16 C15 -179.6(2) . . . . ?
C12 C11 C16 C15 0.8(3) . . . . ?
S11 N12 C17 N13 -178.86(15) . . . . ?
S11 N12 C17 S12 1.6(3) . . . . ?
C18 N13 C17 N12 -178.97(19) . . . . ?
C18 N13 C17 S12 0.6(2) . . . . ?
C19 S12 C17 N12 178.6(2) . . . . ?
C19 S12 C17 N13 -0.90(17) . . . . ?
C17 N13 C18 C19 0.1(3) . . . . ?
N13 C18 C19 S12 -0.8(3) . . . . ?
C17 S12 C19 C18 1.0(2) . . . . ?
C32 O30 C30 O31 177.8(4) . . . . ?
C32 O30 C30 C31 1.2(3) . . . . ?
O31 C30 C31 C32 -176.9(5) . . . . ?
O30 C30 C31 C32 -1.2(3) . . . . ?
C30 O30 C32 C33 118.0(3) . . . . ?
C30 O30 C32 C31 -1.2(3) . . . . ?
C30 C31 C32 C33 -112.9(3) . . . . ?
C30 C31 C32 O30 1.1(2) . . . . ?
C32' O30' C30' O31' 166.0(14) . . . . ?
C32' O30' C30' C31' -3.9(15) . . . . ?
O31' C30' C31' C32' -170.9(6) . . . . ?
O30' C30' C31' C32' 3.8(15) . . . . ?
C30' O30' C32' C33' 117.7(13) . . . . ?
C30' O30' C32' C31' 3.8(15) . . . . ?
C30' C31' C32' C33' -121.2(9) . . . . ?
C30' C31' C32' O30' -3.3(13) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_31
_database_code_depnum_ccdc_archive 'CCDC 2120793'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 4n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, butyronitrile (1:1) solvate'
_chemical_name_common            'Sulfathiazole, butyronitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H7 N'
_chemical_formula_sum            'C13 H16 N4 O2 S2'
_chemical_formula_weight         324.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2478(2)
_cell_length_b                   21.0191(6)
_cell_length_c                   9.0739(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.534(1)
_cell_angle_gamma                90
_cell_volume                     1562.85(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5540
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      40.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.350
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9149
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.545
_diffrn_reflns_theta_max         30.316
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3897
_reflns_number_gt                2723
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  4n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 2.99      61     69     88.4     2.57     452.9   31.20  0.0291  0.0274
2.99 - 2.04     141    141    100.0     2.97     193.3   28.55  0.0375  0.0278
2.04 - 1.61     207    207    100.0     3.16     121.5   26.56  0.0360  0.0283
1.61 - 1.41     202    202    100.0     3.15      80.1   22.04  0.0396  0.0321
1.41 - 1.28     202    202    100.0     3.14      73.3   20.19  0.0422  0.0353
1.28 - 1.19     191    191    100.0     3.15      55.9   17.32  0.0461  0.0403
1.19 - 1.12     210    210    100.0     3.16      61.5   17.55  0.0563  0.0435
1.12 - 1.06     216    216    100.0     3.11      44.9   14.45  0.0585  0.0502
1.06 - 1.01     214    214    100.0     3.13      31.4   12.44  0.0707  0.0579
1.01 - 0.98     159    160     99.4     2.79      22.8    9.88  0.0873  0.0753
0.98 - 0.94     237    237    100.0     2.46      21.8    8.22  0.0902  0.0898
0.94 - 0.91     191    193     99.0     2.28      19.3    7.26  0.0793  0.1018
0.91 - 0.88     247    253     97.6     2.07      17.9    6.50  0.0963  0.1209
0.88 - 0.86     160    170     94.1     1.84      13.9    5.02  0.1213  0.1608
0.86 - 0.84     181    189     95.8     1.67      14.2    4.64  0.1208  0.1698
0.84 - 0.82     184    199     92.5     1.41      11.7    3.51  0.1361  0.2261
0.82 - 0.80     236    250     94.4     1.33      10.3    2.91  0.1680  0.2812
0.80 - 0.78     240    261     92.0     1.24      11.1    3.03  0.1160  0.2804
0.78 - 0.76     213    276     77.2     0.94       8.6    2.20  0.2326  0.4036
0.76 - 0.74     170    323     52.6     0.64       6.7    1.83  0.2466  0.5103
0.74 - 0.71     142    548     25.9     0.29       4.6    1.05  0.3016  0.8656
0.71 - 0.70       6    103      5.8     0.06       8.7    0.51  0.0000  0.6431
#------------------------------------------------------------------------------
0.80 - 0.70     771   1511     51.0     0.63       8.2    2.15  0.1659  0.4206
 Inf - 0.70    4010   4814     83.3     1.94      45.8   10.94  0.0475  0.0621
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.9188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3897
_refine_ls_number_parameters     204
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.080

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.57094(7) 0.14231(3) 0.39754(7) 0.02568(18) Uani 1 1 d . . . . .
S12 S 0.68867(9) 0.13076(3) 0.75613(8) 0.0362(2) Uani 1 1 d . . . . .
O11 O 0.5543(2) 0.12305(8) 0.24377(18) 0.0317(4) Uani 1 1 d . . . . .
O12 O 0.7107(2) 0.18008(8) 0.4517(2) 0.0350(4) Uani 1 1 d . . . . .
N11 N -0.0301(3) 0.27729(11) 0.5102(3) 0.0351(5) Uani 1 1 d D . . . .
H10 H -0.032(4) 0.3039(15) 0.586(3) 0.066(11) Uiso 1 1 d D . . . .
H11 H -0.119(3) 0.2534(14) 0.499(3) 0.056(10) Uiso 1 1 d D . . . .
N12 N 0.5674(2) 0.07631(9) 0.4863(2) 0.0245(4) Uani 1 1 d . . . . .
N13 N 0.5934(3) 0.01827(10) 0.7027(2) 0.0288(5) Uani 1 1 d . . . . .
H17 H 0.553(4) -0.0141(15) 0.652(3) 0.045(9) Uiso 1 1 d . . . . .
C11 C 0.1097(3) 0.24601(11) 0.4865(3) 0.0258(5) Uani 1 1 d . . . . .
C12 C 0.1043(3) 0.19401(11) 0.3892(3) 0.0278(5) Uani 1 1 d . . . . .
H12 H 0.001965 0.179742 0.342079 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2442(3) 0.16348(11) 0.3609(3) 0.0262(5) Uani 1 1 d . . . . .
H13 H 0.238435 0.128368 0.294585 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3958(3) 0.18396(11) 0.4297(3) 0.0237(5) Uani 1 1 d . . . . .
C15 C 0.4040(3) 0.23552(11) 0.5266(3) 0.0255(5) Uani 1 1 d . . . . .
H15 H 0.506527 0.249673 0.573385 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2625(3) 0.26590(11) 0.5543(3) 0.0256(5) Uani 1 1 d . . . . .
H16 H 0.268669 0.301010 0.620639 0.031 Uiso 1 1 calc R U . . .
C17 C 0.6103(3) 0.07304(11) 0.6311(3) 0.0248(5) Uani 1 1 d . . . . .
C18 C 0.6373(3) 0.01982(13) 0.8541(3) 0.0349(6) Uani 1 1 d . . . . .
H18 H 0.630952 -0.015798 0.917654 0.042 Uiso 1 1 calc R U . . .
C19 C 0.6896(4) 0.07693(14) 0.9005(3) 0.0413(7) Uani 1 1 d . . . . .
H19 H 0.723512 0.087077 1.001356 0.050 Uiso 1 1 calc R U . . .
N31 N 0.0937(4) 0.11722(14) 1.0194(3) 0.0607(8) Uani 1 1 d . . . . .
C31 C 0.1335(4) 0.11537(15) 0.9041(4) 0.0475(8) Uani 1 1 d . . . . .
C32 C 0.1818(6) 0.1096(2) 0.7544(5) 0.0790(13) Uani 1 1 d . . . . .
H32A H 0.115635 0.139834 0.689160 0.095 Uiso 1 1 calc R U . . .
H32B H 0.297249 0.122934 0.757621 0.095 Uiso 1 1 calc R U . . .
C33 C 0.1662(8) 0.0493(3) 0.6893(6) 0.114(2) Uani 1 1 d . . . . .
H33A H 0.145239 0.057746 0.581447 0.137 Uiso 1 1 calc R U . . .
H33B H 0.277317 0.030886 0.705365 0.137 Uiso 1 1 calc R U . . .
C34 C 0.0644(7) -0.0002(2) 0.7135(5) 0.0997(18) Uani 1 1 d . . . . .
H34A H 0.116613 -0.040535 0.691962 0.150 Uiso 1 1 calc R U . . .
H34B H -0.038306 0.004287 0.648501 0.150 Uiso 1 1 calc R U . . .
H34C H 0.042066 0.000145 0.817267 0.150 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.4393(18) . ?
S11 O11 1.4444(18) . ?
S11 N12 1.606(2) . ?
S11 C14 1.742(2) . ?
S12 C19 1.731(3) . ?
S12 C17 1.735(2) . ?
N11 C11 1.365(3) . ?
N11 H10 0.88(2) . ?
N11 H11 0.88(2) . ?
N12 C17 1.323(3) . ?
N13 C17 1.337(3) . ?
N13 C18 1.381(3) . ?
N13 H17 0.87(3) . ?
C11 C16 1.402(3) . ?
C11 C12 1.403(3) . ?
C12 C13 1.370(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.328(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C31 1.132(4) . ?
C31 C32 1.463(5) . ?
C32 C33 1.397(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.371(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 117.95(11) . . ?
O12 S11 N12 111.40(11) . . ?
O11 S11 N12 103.73(10) . . ?
O12 S11 C14 108.24(11) . . ?
O11 S11 C14 108.24(11) . . ?
N12 S11 C14 106.70(11) . . ?
C19 S12 C17 90.40(13) . . ?
C11 N11 H10 121(2) . . ?
C11 N11 H11 114(2) . . ?
H10 N11 H11 111.3(16) . . ?
C17 N12 S11 121.67(16) . . ?
C17 N13 C18 115.6(2) . . ?
C17 N13 H17 118(2) . . ?
C18 N13 H17 126(2) . . ?
N11 C11 C16 121.4(2) . . ?
N11 C11 C12 120.5(2) . . ?
C16 C11 C12 118.1(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 S11 121.01(18) . . ?
C13 C14 S11 119.10(18) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N12 C17 N13 119.8(2) . . ?
N12 C17 S12 130.59(18) . . ?
N13 C17 S12 109.65(18) . . ?
C19 C18 N13 112.1(2) . . ?
C19 C18 H18 124.0 . . ?
N13 C18 H18 124.0 . . ?
C18 C19 S12 112.2(2) . . ?
C18 C19 H19 123.9 . . ?
S12 C19 H19 123.9 . . ?
N31 C31 C32 177.0(4) . . ?
C33 C32 C31 116.5(3) . . ?
C33 C32 H32A 108.2 . . ?
C31 C32 H32A 108.2 . . ?
C33 C32 H32B 108.2 . . ?
C31 C32 H32B 108.2 . . ?
H32A C32 H32B 107.3 . . ?
C34 C33 C32 130.5(4) . . ?
C34 C33 H33A 104.7 . . ?
C32 C33 H33A 104.7 . . ?
C34 C33 H33B 104.7 . . ?
C32 C33 H33B 104.7 . . ?
H33A C33 H33B 105.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 39.1(2) . . . . ?
O11 S11 N12 C17 166.95(18) . . . . ?
C14 S11 N12 C17 -78.9(2) . . . . ?
N11 C11 C12 C13 177.9(2) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C12 C13 C14 S11 177.44(18) . . . . ?
O12 S11 C14 C15 -15.2(2) . . . . ?
O11 S11 C14 C15 -144.12(19) . . . . ?
N12 S11 C14 C15 104.8(2) . . . . ?
O12 S11 C14 C13 167.26(18) . . . . ?
O11 S11 C14 C13 38.3(2) . . . . ?
N12 S11 C14 C13 -72.8(2) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
S11 C14 C15 C16 -177.38(18) . . . . ?
C14 C15 C16 C11 -0.1(4) . . . . ?
N11 C11 C16 C15 -177.9(2) . . . . ?
C12 C11 C16 C15 0.1(4) . . . . ?
S11 N12 C17 N13 174.71(17) . . . . ?
S11 N12 C17 S12 -4.5(3) . . . . ?
C18 N13 C17 N12 -178.4(2) . . . . ?
C18 N13 C17 S12 1.0(3) . . . . ?
C19 S12 C17 N12 178.1(2) . . . . ?
C19 S12 C17 N13 -1.25(19) . . . . ?
C17 N13 C18 C19 -0.1(3) . . . . ?
N13 C18 C19 S12 -0.9(3) . . . . ?
C17 S12 C19 C18 1.2(2) . . . . ?
C31 C32 C33 C34 26.0(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.88(2) 2.17(2) 3.005(3) 158(3) 4_566 yes
N11 H11 O12 0.88(2) 2.10(2) 2.961(3) 165(3) 1_455 yes
N13 H17 O11 0.87(3) 2.67(3) 3.267(3) 127(2) 3_656 yes
N13 H17 N12 0.87(3) 2.00(3) 2.852(3) 169(3) 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_35
_database_code_depnum_ccdc_archive 'CCDC 2120796'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 8n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1,9-nonanedinitrile (2:1) solvate'
_chemical_name_common            'Sulfathiazole, azelanitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C9 H14 N2'
_chemical_formula_sum            'C27 H32 N8 O4 S4'
_chemical_formula_weight         660.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3630(17)
_cell_length_b                   21.146(4)
_cell_length_c                   9.1160(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.76(3)
_cell_angle_gamma                90
_cell_volume                     1604.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6087
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      21.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.342
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8090
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.616
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.024
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2768
_reflns_number_gt                2220
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  8n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.02      55     68     80.9     2.54     186.1   25.33  0.0212  0.0367
3.02 - 2.08     131    136     96.3     3.07      74.7   23.09  0.0272  0.0385
2.08 - 1.66     181    187     96.8     3.11      46.0   20.88  0.0307  0.0381
1.66 - 1.46     177    182     97.3     3.09      34.2   18.45  0.0416  0.0430
1.46 - 1.32     194    196     99.0     3.13      28.0   15.73  0.0512  0.0504
1.32 - 1.23     185    188     98.4     3.05      21.7   12.21  0.0572  0.0643
1.23 - 1.16     170    170    100.0     3.10      23.1   11.88  0.0603  0.0684
1.16 - 1.10     195    196     99.5     3.07      18.2   10.97  0.0670  0.0749
1.10 - 1.05     189    189    100.0     3.08      15.1    8.85  0.0794  0.0875
1.05 - 1.01     187    188     99.5     2.97      10.3    8.09  0.1066  0.1087
1.01 - 0.98     164    165     99.4     3.02       8.4    6.16  0.1335  0.1328
0.98 - 0.95     172    172    100.0     2.95       7.2    5.41  0.1520  0.1573
0.95 - 0.92     194    194    100.0     2.81       6.4    4.67  0.1679  0.1749
0.92 - 0.89     242    245     98.8     2.36       5.1    3.87  0.1956  0.2235
0.89 - 0.87     162    171     94.7     2.13       5.7    3.60  0.1929  0.2358
0.87 - 0.85     169    185     91.4     1.96       3.6    2.68  0.2296  0.3512
0.85 - 0.83     168    197     85.3     1.69       3.7    2.29  0.2509  0.3837
0.83 - 0.81     186    236     78.8     1.50       3.5    2.15  0.2915  0.4209
0.81 - 0.79     169    257     65.8     1.00       2.9    1.61  0.3276  0.5681
0.79 - 0.76     199    405     49.1     0.61       2.7    1.26  0.3496  0.7150
0.76 - 0.72     146    779     18.7     0.20       1.9    0.87  0.3332  1.0967
#------------------------------------------------------------------------------
0.82 - 0.72     611   1559     39.2     0.54       2.7    1.39  0.3184  0.6722
 Inf - 0.72    3635   4706     77.2     2.00      18.0    8.35  0.0585  0.0863
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The (non-centrosymmetric) azelanitrile molecule is disordered across the
inversion centre. The two ends of the molecule are superimposed in the
asymmetric unit. Restraints are applied to control the geometry.

This data set has some problems. Although the R(int) value looks good,
the R-factors stick at R1 = 0.12, wR2 = 0.30. The problem is not
just due to the disordered solvent, since removing it and applying SQUEEZE
does not improve the result. All of the most disagreeable relections have
F(obs) larger than F(calc), which indicates the probable presence of some
other crystal component. TWINROTMAT does not identify any potential twin law.
This is part of a large set of isostructural compounds, so there is no concern
over the correctness of the structure.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+23.8415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2768
_refine_ls_number_parameters     208
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1437
_refine_ls_R_factor_gt           0.1259
_refine_ls_wR_factor_ref         0.3033
_refine_ls_wR_factor_gt          0.2951
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.215
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.122

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.5372(3) 0.14485(10) 0.4001(2) 0.0278(6) Uani 1 1 d . . . . .
S12 S 0.6334(4) 0.13559(12) 0.7599(3) 0.0542(9) Uani 1 1 d . . . . .
O11 O 0.5208(8) 0.1247(3) 0.2466(7) 0.0344(15) Uani 1 1 d . . . . .
O12 O 0.6727(8) 0.1836(3) 0.4516(8) 0.0372(16) Uani 1 1 d . . . . .
N11 N -0.0598(10) 0.2710(4) 0.5298(10) 0.042(2) Uani 1 1 d . . . . .
H10 H -0.055916 0.304073 0.592242 0.063 Uiso 1 1 d R U . . .
H11 H -0.155056 0.257162 0.487132 0.063 Uiso 1 1 d R U . . .
N12 N 0.5371(9) 0.0796(3) 0.4883(8) 0.0268(16) Uani 1 1 d . . . . .
N13 N 0.5697(10) 0.0209(4) 0.7027(8) 0.0359(19) Uani 1 1 d . . . . .
H17 H 0.543662 -0.014556 0.655915 0.054 Uiso 1 1 calc R U . . .
C11 C 0.0803(12) 0.2416(4) 0.5001(10) 0.033(2) Uani 1 1 d . . . . .
C12 C 0.0727(11) 0.1914(4) 0.3997(10) 0.032(2) Uani 1 1 d . . . . .
H12 H -0.027574 0.176584 0.354332 0.038 Uiso 1 1 calc R U . . .
C13 C 0.2184(10) 0.1634(4) 0.3679(10) 0.030(2) Uani 1 1 d . . . . .
H13 H 0.216282 0.129614 0.299079 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3627(10) 0.1842(4) 0.4346(9) 0.0247(18) Uani 1 1 d . . . . .
C15 C 0.3679(11) 0.2342(4) 0.5335(10) 0.029(2) Uani 1 1 d . . . . .
H15 H 0.468336 0.248655 0.579163 0.034 Uiso 1 1 calc R U . . .
C16 C 0.2299(11) 0.2626(4) 0.5652(10) 0.032(2) Uani 1 1 d . . . . .
H16 H 0.234773 0.297055 0.632358 0.038 Uiso 1 1 calc R U . . .
C17 C 0.5738(11) 0.0766(4) 0.6328(9) 0.030(2) Uani 1 1 d . . . . .
C18 C 0.6097(17) 0.0233(5) 0.8548(11) 0.054(3) Uani 1 1 d . . . . .
H18 H 0.613775 -0.012712 0.917442 0.065 Uiso 1 1 calc R U . . .
C19 C 0.641(2) 0.0815(5) 0.9015(12) 0.067(4) Uani 1 1 d . . . . .
H19 H 0.665836 0.092373 1.002373 0.081 Uiso 1 1 calc R U . . .
N31 N 0.009(2) 0.0881(10) 1.0842(19) 0.064(6) Uani 0.5 1 d D . P A 1
C31 C 0.0658(18) 0.1160(8) 1.0010(13) 0.100(6) Uani 0.5 1 d D . P A 1
C32 C 0.110(3) 0.1371(7) 0.8621(16) 0.070(9) Uani 0.5 1 d D . P A 1
H32A H 0.197887 0.168542 0.879669 0.084 Uiso 0.5 1 calc R U P A 1
H32B H 0.017039 0.158810 0.808484 0.084 Uiso 0.5 1 calc R U P A 1
N32 N 0.0658(18) 0.1160(8) 1.0010(13) 0.100(6) Uani 0.5 1 d D . P A 2
C36 C 0.135(3) 0.1032(15) 0.908(2) 0.077(10) Uani 0.5 1 d D U P A 2
C33 C 0.1665(13) 0.0836(8) 0.7633(14) 0.095(6) Uani 1 1 d D . . . .
H33A H 0.243772 0.100655 0.697884 0.114 Uiso 1 1 calc R U . A 1
H33B H 0.221073 0.050118 0.825465 0.114 Uiso 1 1 calc R U . A 1
C34 C 0.0210(12) 0.0561(5) 0.6710(11) 0.054(3) Uani 1 1 d D . . . .
H34A H -0.044894 0.090944 0.624260 0.064 Uiso 1 1 calc R U . . .
H34B H -0.045988 0.032388 0.735692 0.064 Uiso 1 1 calc R U . . .
C35 C 0.0729(14) 0.0119(5) 0.5514(10) 0.051(3) Uani 1 1 d D . . . .
H35A H 0.131059 -0.024711 0.598508 0.061 Uiso 1 1 calc R U . . .
H35B H 0.147497 0.034714 0.492161 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.438(6) . ?
S11 O11 1.457(6) . ?
S11 N12 1.597(7) . ?
S11 C14 1.735(8) . ?
S12 C19 1.720(11) . ?
S12 C17 1.741(9) . ?
N11 C11 1.376(12) . ?
N11 H10 0.9000 . ?
N11 H11 0.9000 . ?
N12 C17 1.324(11) . ?
N13 C17 1.340(11) . ?
N13 C18 1.394(12) . ?
N13 H17 0.8800 . ?
C11 C12 1.400(12) . ?
C11 C16 1.402(13) . ?
C12 C13 1.411(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.368(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(12) . ?
C15 C16 1.357(13) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.321(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C31 1.105(9) . ?
C31 C32 1.426(8) . ?
C32 C33 1.548(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
N32 C36 1.106(9) . ?
C36 C33 1.434(9) . ?
C33 C34 1.524(9) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.531(8) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C35 1.55(2) 3_556 ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 118.4(4) . . ?
O12 S11 N12 111.6(4) . . ?
O11 S11 N12 103.0(4) . . ?
O12 S11 C14 108.5(4) . . ?
O11 S11 C14 108.3(4) . . ?
N12 S11 C14 106.2(4) . . ?
C19 S12 C17 90.6(5) . . ?
C11 N11 H10 119.9 . . ?
C11 N11 H11 120.1 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 122.0(6) . . ?
C17 N13 C18 115.3(8) . . ?
C17 N13 H17 122.4 . . ?
C18 N13 H17 122.4 . . ?
N11 C11 C12 119.2(8) . . ?
N11 C11 C16 121.0(8) . . ?
C12 C11 C16 119.8(9) . . ?
C11 C12 C13 118.0(8) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C14 C13 C12 121.1(8) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.1(8) . . ?
C13 C14 S11 119.1(7) . . ?
C15 C14 S11 120.7(7) . . ?
C16 C15 C14 120.3(8) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 120.8(8) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N12 C17 N13 120.0(8) . . ?
N12 C17 S12 130.6(7) . . ?
N13 C17 S12 109.4(6) . . ?
C19 C18 N13 111.9(10) . . ?
C19 C18 H18 124.0 . . ?
N13 C18 H18 124.0 . . ?
C18 C19 S12 112.7(9) . . ?
C18 C19 H19 123.6 . . ?
S12 C19 H19 123.6 . . ?
N31 C31 C32 160.8(19) . . ?
C31 C32 C33 114.1(9) . . ?
C31 C32 H32A 108.7 . . ?
C33 C32 H32A 108.7 . . ?
C31 C32 H32B 108.7 . . ?
C33 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
N32 C36 C33 159(3) . . ?
C36 C33 C34 114.2(15) . . ?
C34 C33 C32 109.1(8) . . ?
C34 C33 H33A 109.9 . . ?
C32 C33 H33A 109.9 . . ?
C34 C33 H33B 109.9 . . ?
C32 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
C33 C34 C35 111.0(7) . . ?
C33 C34 H34A 109.4 . . ?
C35 C34 H34A 109.4 . . ?
C33 C34 H34B 109.4 . . ?
C35 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C34 C35 C35 111.6(11) . 3_556 ?
C34 C35 H35A 109.3 . . ?
C35 C35 H35A 109.3 3_556 . ?
C34 C35 H35B 109.3 . . ?
C35 C35 H35B 109.3 3_556 . ?
H35A C35 H35B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 41.6(9) . . . . ?
O11 S11 N12 C17 169.7(7) . . . . ?
C14 S11 N12 C17 -76.5(8) . . . . ?
N11 C11 C12 C13 178.1(9) . . . . ?
C16 C11 C12 C13 0.1(14) . . . . ?
C11 C12 C13 C14 0.8(14) . . . . ?
C12 C13 C14 C15 -1.1(13) . . . . ?
C12 C13 C14 S11 176.0(7) . . . . ?
O12 S11 C14 C13 166.1(7) . . . . ?
O11 S11 C14 C13 36.4(8) . . . . ?
N12 S11 C14 C13 -73.7(8) . . . . ?
O12 S11 C14 C15 -16.8(8) . . . . ?
O11 S11 C14 C15 -146.5(7) . . . . ?
N12 S11 C14 C15 103.4(7) . . . . ?
C13 C14 C15 C16 0.4(13) . . . . ?
S11 C14 C15 C16 -176.7(7) . . . . ?
C14 C15 C16 C11 0.6(14) . . . . ?
N11 C11 C16 C15 -178.7(9) . . . . ?
C12 C11 C16 C15 -0.8(14) . . . . ?
S11 N12 C17 N13 179.0(7) . . . . ?
S11 N12 C17 S12 -1.9(13) . . . . ?
C18 N13 C17 N12 -179.7(10) . . . . ?
C18 N13 C17 S12 1.0(12) . . . . ?
C19 S12 C17 N12 178.6(11) . . . . ?
C19 S12 C17 N13 -2.3(9) . . . . ?
C17 N13 C18 C19 1.3(17) . . . . ?
N13 C18 C19 S12 -3.1(17) . . . . ?
C17 S12 C19 C18 3.1(13) . . . . ?
N31 C31 C32 C33 -48(7) . . . . ?
N32 C36 C33 C34 -14(10) . . . . ?
C31 C32 C33 C34 88.1(17) . . . . ?
C36 C33 C34 C35 -155.7(18) . . . . ?
C32 C33 C34 C35 169.4(11) . . . . ?
C33 C34 C35 C35 -175.2(13) . . . 3_556 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.90 2.12 2.993(10) 164.3 4_566 yes
N11 H11 O12 0.90 2.12 2.935(10) 149.6 1_455 yes
N13 H17 O11 0.88 2.57 3.216(10) 131.0 3_656 yes
N13 H17 N12 0.88 1.97 2.834(10) 165.6 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_29
_database_code_depnum_ccdc_archive 'CCDC 2120790'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 2n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1,10-decanedinitrile (2:1) solvate'
_chemical_name_common            'Sulfathiazole, sebaconitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C10 H16 N2'
_chemical_formula_sum            'C28 H34 N8 O4 S4'
_chemical_formula_weight         674.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.523(2)
_cell_length_b                   21.073(4)
_cell_length_c                   9.087(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.54(3)
_cell_angle_gamma                90
_cell_volume                     1621.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13649
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      30.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             708
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.340
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13649
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.613
_diffrn_reflns_theta_max         30.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4261
_reflns_number_gt                2635
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  2n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.09      57     64     89.1     3.97     237.2   39.55  0.0286  0.0217
3.09 - 2.11     132    132    100.0     4.35      99.0   30.34  0.0278  0.0229
2.11 - 1.68     189    189    100.0     4.59      58.7   28.10  0.0357  0.0238
1.68 - 1.46     189    189    100.0     4.54      41.8   24.16  0.0414  0.0292
1.46 - 1.32     205    205    100.0     4.59      32.9   20.75  0.0440  0.0329
1.32 - 1.23     181    181    100.0     4.48      26.9   17.04  0.0548  0.0395
1.23 - 1.16     185    185    100.0     4.44      29.2   16.81  0.0570  0.0407
1.16 - 1.10     192    192    100.0     4.48      21.1   14.06  0.0733  0.0513
1.10 - 1.05     191    191    100.0     4.46      20.7   13.09  0.0737  0.0543
1.05 - 1.01     185    185    100.0     4.47      12.5   10.65  0.1027  0.0724
1.01 - 0.97     227    227    100.0     4.04      10.0    7.64  0.1263  0.0977
0.97 - 0.94     187    187    100.0     3.55       9.6    7.04  0.1451  0.1127
0.94 - 0.91     208    208    100.0     3.46       8.4    6.09  0.1542  0.1314
0.91 - 0.89     164    164    100.0     2.98       7.4    5.01  0.1556  0.1642
0.89 - 0.87     172    172    100.0     2.70       6.7    4.02  0.1883  0.1953
0.87 - 0.85     187    188     99.5     2.49       5.9    3.51  0.2224  0.2387
0.85 - 0.83     206    208     99.0     2.21       6.0    3.26  0.2048  0.2604
0.83 - 0.81     237    240     98.8     1.90       4.5    2.28  0.2544  0.3894
0.81 - 0.80     118    123     95.9     1.86       4.9    2.38  0.2375  0.3688
0.80 - 0.78     245    249     98.4     1.77       4.3    1.90  0.2529  0.4527
0.78 - 0.77     126    140     90.0     1.47       4.0    1.74  0.3220  0.5359
#------------------------------------------------------------------------------
0.87 - 0.77    1119   1148     97.5     1.97       5.0    2.53  0.2366  0.3543
 Inf - 0.77    3783   3819     99.1     3.45      22.9   11.21  0.0570  0.0619
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4261
_refine_ls_number_parameters     212
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.065

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.55324(6) 0.14525(2) 0.40400(6) 0.02820(16) Uani 1 1 d . . . . .
S12 S 0.64619(6) 0.13330(2) 0.76550(6) 0.03551(17) Uani 1 1 d . . . . .
O11 O 0.53861(17) 0.12735(6) 0.24957(16) 0.0349(4) Uani 1 1 d . . . . .
O12 O 0.68538(15) 0.18449(6) 0.45917(17) 0.0380(4) Uani 1 1 d . . . . .
N11 N -0.0373(2) 0.26548(9) 0.5394(2) 0.0403(5) Uani 1 1 d D . . . .
H10 H -0.040(2) 0.2945(10) 0.607(2) 0.053(7) Uiso 1 1 d D . . . .
H11 H -0.123(2) 0.2438(9) 0.525(2) 0.044(7) Uiso 1 1 d D . . . .
N12 N 0.55318(18) 0.07895(7) 0.48976(18) 0.0266(4) Uani 1 1 d . . . . .
N13 N 0.5747(2) 0.01936(8) 0.70413(19) 0.0292(4) Uani 1 1 d . . . . .
H17 H 0.541(2) -0.0119(10) 0.651(3) 0.033(6) Uiso 1 1 d . . . . .
C11 C 0.1002(2) 0.23913(9) 0.5059(2) 0.0281(4) Uani 1 1 d . . . . .
C12 C 0.0980(2) 0.18905(9) 0.4037(2) 0.0294(4) Uani 1 1 d . . . . .
H12 H -0.000060 0.173611 0.357205 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2358(2) 0.16236(9) 0.3707(2) 0.0294(5) Uani 1 1 d . . . . .
H13 H 0.232666 0.128219 0.302131 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3814(2) 0.18476(9) 0.4367(2) 0.0254(4) Uani 1 1 d . . . . .
C15 C 0.3849(2) 0.23517(8) 0.5366(2) 0.0277(4) Uani 1 1 d . . . . .
H15 H 0.483367 0.250914 0.581319 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2468(2) 0.26220(9) 0.5707(2) 0.0291(5) Uani 1 1 d . . . . .
H16 H 0.250416 0.296643 0.638479 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5866(2) 0.07514(9) 0.6357(2) 0.0263(4) Uani 1 1 d . . . . .
C18 C 0.6104(2) 0.02035(10) 0.8549(2) 0.0368(5) Uani 1 1 d . . . . .
H18 H 0.607722 -0.016203 0.915777 0.044 Uiso 1 1 calc R U . . .
C19 C 0.6496(3) 0.07833(10) 0.9075(3) 0.0401(5) Uani 1 1 d . . . . .
H19 H 0.675755 0.088016 1.009488 0.048 Uiso 1 1 calc R U . . .
N31 N 0.0156(3) 0.09100(12) 1.0846(3) 0.0656(7) Uani 1 1 d . . . . .
C31 C 0.0710(3) 0.11181(13) 0.9865(3) 0.0508(7) Uani 1 1 d . . . . .
C32 C 0.1444(3) 0.13799(12) 0.8636(3) 0.0578(7) Uani 1 1 d . . . . .
H32A H 0.243917 0.159405 0.902631 0.069 Uiso 1 1 calc R U . . .
H32B H 0.073406 0.170410 0.813134 0.069 Uiso 1 1 calc R U . . .
C33 C 0.1808(3) 0.08794(12) 0.7505(3) 0.0496(6) Uani 1 1 d . . . . .
H33A H 0.246456 0.107481 0.679588 0.059 Uiso 1 1 calc R U . . .
H33B H 0.243243 0.053435 0.802704 0.059 Uiso 1 1 calc R U . . .
C34 C 0.0342(2) 0.05956(10) 0.6647(2) 0.0380(5) Uani 1 1 d . . . . .
H34A H -0.030690 0.094182 0.615720 0.046 Uiso 1 1 calc R U . . .
H34B H -0.029262 0.038278 0.734952 0.046 Uiso 1 1 calc R U . . .
C35 C 0.0721(2) 0.01198(11) 0.5482(3) 0.0390(5) Uani 1 1 d . . . . .
H35A H 0.144571 0.032075 0.484285 0.047 Uiso 1 1 calc R U . . .
H35B H 0.127949 -0.024630 0.598364 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.4404(14) . ?
S11 O11 1.4447(15) . ?
S11 N12 1.5998(16) . ?
S11 C14 1.7397(18) . ?
S12 C19 1.732(2) . ?
S12 C17 1.736(2) . ?
N11 C11 1.362(2) . ?
N11 H10 0.870(17) . ?
N11 H11 0.861(16) . ?
N12 C17 1.327(3) . ?
N13 C17 1.339(2) . ?
N13 C18 1.369(3) . ?
N13 H17 0.85(2) . ?
C11 C12 1.405(3) . ?
C11 C16 1.406(3) . ?
C12 C13 1.366(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(3) . ?
C15 C16 1.374(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.340(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C31 1.143(3) . ?
C31 C32 1.450(4) . ?
C32 C33 1.529(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.518(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.519(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C35 1.513(4) 3_556 ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 117.74(9) . . ?
O12 S11 N12 112.05(9) . . ?
O11 S11 N12 103.91(8) . . ?
O12 S11 C14 107.82(9) . . ?
O11 S11 C14 108.03(9) . . ?
N12 S11 C14 106.73(8) . . ?
C19 S12 C17 90.73(11) . . ?
C11 N11 H10 122.7(14) . . ?
C11 N11 H11 119.3(13) . . ?
H10 N11 H11 112.7(14) . . ?
C17 N12 S11 121.85(13) . . ?
C17 N13 C18 115.54(18) . . ?
C17 N13 H17 117.0(15) . . ?
C18 N13 H17 127.4(15) . . ?
N11 C11 C12 120.46(18) . . ?
N11 C11 C16 120.79(18) . . ?
C12 C11 C16 118.74(17) . . ?
C13 C12 C11 120.51(17) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.67(18) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.25(17) . . ?
C15 C14 S11 121.29(14) . . ?
C13 C14 S11 119.26(15) . . ?
C16 C15 C14 120.46(18) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.35(18) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N12 C17 N13 119.87(17) . . ?
N12 C17 S12 130.48(14) . . ?
N13 C17 S12 109.64(15) . . ?
C19 C18 N13 112.9(2) . . ?
C19 C18 H18 123.6 . . ?
N13 C18 H18 123.6 . . ?
C18 C19 S12 111.19(17) . . ?
C18 C19 H19 124.4 . . ?
S12 C19 H19 124.4 . . ?
N31 C31 C32 178.8(3) . . ?
C31 C32 C33 113.2(2) . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
H32A C32 H32B 107.8 . . ?
C34 C33 C32 113.53(19) . . ?
C34 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 C35 112.96(17) . . ?
C33 C34 H34A 109.0 . . ?
C35 C34 H34A 109.0 . . ?
C33 C34 H34B 109.0 . . ?
C35 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C35 C35 C34 113.6(2) 3_556 . ?
C35 C35 H35A 108.8 3_556 . ?
C34 C35 H35A 108.8 . . ?
C35 C35 H35B 108.8 3_556 . ?
C34 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 42.37(16) . . . . ?
O11 S11 N12 C17 170.51(14) . . . . ?
C14 S11 N12 C17 -75.44(16) . . . . ?
N11 C11 C12 C13 -179.7(2) . . . . ?
C16 C11 C12 C13 1.5(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C12 C13 C14 S11 174.54(15) . . . . ?
O12 S11 C14 C15 -16.45(19) . . . . ?
O11 S11 C14 C15 -144.68(16) . . . . ?
N12 S11 C14 C15 104.11(16) . . . . ?
O12 S11 C14 C13 168.75(15) . . . . ?
O11 S11 C14 C13 40.52(18) . . . . ?
N12 S11 C14 C13 -70.69(17) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
S11 C14 C15 C16 -174.28(15) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
N11 C11 C16 C15 179.82(19) . . . . ?
C12 C11 C16 C15 -1.3(3) . . . . ?
S11 N12 C17 N13 175.42(13) . . . . ?
S11 N12 C17 S12 -4.0(2) . . . . ?
C18 N13 C17 N12 -179.50(16) . . . . ?
C18 N13 C17 S12 0.0(2) . . . . ?
C19 S12 C17 N12 178.82(18) . . . . ?
C19 S12 C17 N13 -0.64(14) . . . . ?
C17 N13 C18 C19 0.8(3) . . . . ?
N13 C18 C19 S12 -1.3(2) . . . . ?
C17 S12 C19 C18 1.11(17) . . . . ?
C31 C32 C33 C34 68.2(3) . . . . ?
C32 C33 C34 C35 177.6(2) . . . . ?
C33 C34 C35 C35 -174.4(2) . . . 3_556 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.870(17) 2.155(17) 2.981(2) 158.3(18) 4_566 yes
N11 H11 O12 0.861(16) 2.087(17) 2.939(2) 170.1(18) 1_455 yes
N13 H17 O11 0.85(2) 2.71(2) 3.280(2) 125.9(18) 3_656 yes
N13 H17 N12 0.85(2) 2.01(2) 2.854(2) 174(2) 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_28
_database_code_depnum_ccdc_archive 'CCDC 2120789'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 1n
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_28                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: the available data extend to 0.97 angstrom resolution. The
intensity statistics are included in the CIF. Despite this deficiency, the
refinement is good, and the structure is not in doubt.
;
_vrf_PLAT029_28                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.931 Why?  
RESPONSE: These are the data that are available. Despite this deficiency, the
refinement is good, and the structure is not in doubt.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1,8-octanedinitrile (2:1) solvate'
_chemical_name_common            'Sulfathiazole, suberonitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C8 H12 N2'
_chemical_formula_sum            'C26 H30 N8 O4 S4'
_chemical_formula_weight         646.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.010(2)
_cell_length_b                   20.820(4)
_cell_length_c                   8.990(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.65(3)
_cell_angle_gamma                90
_cell_volume                     1494.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4276
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      21.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.366
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4276
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.553
_diffrn_reflns_theta_max         21.542
_diffrn_reflns_theta_full        21.542
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.931
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.931
_reflns_number_total             1607
_reflns_number_gt                1300
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  1n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.77      26     35     74.3     2.46     203.2   25.06  0.0309  0.0308
3.77 - 2.66      57     58     98.3     3.48     150.8   23.98  0.0354  0.0316
2.66 - 2.14      86     86    100.0     3.51      87.9   23.24  0.0279  0.0334
2.14 - 1.86      83     85     97.6     3.31      64.2   21.27  0.0359  0.0352
1.86 - 1.70      80     80    100.0     3.60      54.5   19.23  0.0410  0.0368
1.70 - 1.57      87     91     95.6     3.49      39.8   17.84  0.0402  0.0386
1.57 - 1.48      79     80     98.8     3.26      31.7   15.55  0.0429  0.0445
1.48 - 1.40      94     95     98.9     2.92      42.4   15.32  0.0419  0.0462
1.40 - 1.34      78     78    100.0     2.73      29.8   11.69  0.0609  0.0552
1.34 - 1.28      85     98     86.7     2.18      29.9   13.04  0.0558  0.0602
1.28 - 1.24      84     85     98.8     2.39      25.0   10.50  0.0493  0.0619
1.24 - 1.20      82     82    100.0     2.56      33.1   12.44  0.0461  0.0592
1.20 - 1.17      80     80    100.0     2.49      21.0   10.06  0.0623  0.0705
1.17 - 1.13      87     94     92.6     2.17      26.6   10.63  0.0662  0.0690
1.13 - 1.10      94    107     87.9     1.97      24.8    9.71  0.0724  0.0740
1.10 - 1.08      67     74     90.5     1.82      27.0   10.16  0.0551  0.0801
1.08 - 1.05      97    100     97.0     1.87      18.8    8.10  0.0780  0.0929
1.05 - 1.03      89     94     94.7     1.69      20.5    7.51  0.0721  0.0941
1.03 - 1.01      67     69     97.1     1.74      13.8    6.16  0.1065  0.1192
1.01 - 0.99      94    106     88.7     1.62      13.5    5.77  0.0998  0.1211
0.99 - 0.97      71    121     58.7     1.07      11.3    5.45  0.0945  0.1380
#------------------------------------------------------------------------------
1.07 - 0.97     380    450     84.4     1.53      15.6    6.49  0.0865  0.1093
 Inf - 0.97    1667   1798     92.7     2.43      39.3   12.95  0.0432  0.0511
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0249P)²+1.4645P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1607
_refine_ls_number_parameters     203
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.051

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.59753(11) 0.14108(4) 0.39762(10) 0.0216(3) Uani 1 1 d . . . . .
S12 S 0.68592(13) 0.12990(5) 0.75177(11) 0.0329(3) Uani 1 1 d . . . . .
O11 O 0.5897(3) 0.12135(11) 0.2474(3) 0.0262(6) Uani 1 1 d . . . . .
O12 O 0.7418(3) 0.17618(11) 0.4546(3) 0.0272(7) Uani 1 1 d . . . . .
N11 N -0.0079(4) 0.27989(17) 0.5145(4) 0.0315(9) Uani 1 1 d D . . . .
H10 H -0.012(4) 0.3056(16) 0.585(3) 0.037(13) Uiso 1 1 d D . . . .
H11 H -0.100(3) 0.2622(14) 0.491(3) 0.018(11) Uiso 1 1 d D . . . .
N12 N 0.5780(3) 0.07567(13) 0.4852(3) 0.0195(7) Uani 1 1 d . . . . .
N13 N 0.5788(4) 0.01866(15) 0.6989(3) 0.0226(8) Uani 1 1 d . . . . .
H17 H 0.529(5) -0.016(2) 0.646(4) 0.049(13) Uiso 1 1 d . . . . .
C11 C 0.1330(4) 0.24906(17) 0.4865(4) 0.0208(9) Uani 1 1 d . . . . .
C12 C 0.1287(4) 0.19930(17) 0.3849(4) 0.0219(9) Uani 1 1 d . . . . .
H12 H 0.024774 0.186816 0.334727 0.026 Uiso 1 1 calc R U . . .
C13 C 0.2706(4) 0.16803(16) 0.3557(4) 0.0200(9) Uani 1 1 d . . . . .
H13 H 0.265195 0.133363 0.286790 0.024 Uiso 1 1 calc R U . . .
C14 C 0.4228(4) 0.18614(16) 0.4253(4) 0.0181(9) Uani 1 1 d . . . . .
C15 C 0.4296(4) 0.23619(17) 0.5238(4) 0.0217(9) Uani 1 1 d . . . . .
H15 H 0.534197 0.249271 0.571717 0.026 Uiso 1 1 calc R U . . .
C16 C 0.2863(4) 0.26739(16) 0.5533(4) 0.0219(9) Uani 1 1 d . . . . .
H16 H 0.292353 0.302423 0.621270 0.026 Uiso 1 1 calc R U . . .
C17 C 0.6088(4) 0.07265(17) 0.6278(4) 0.0197(9) Uani 1 1 d . . . . .
C18 C 0.6158(5) 0.02073(19) 0.8477(4) 0.0303(10) Uani 1 1 d . . . . .
H18 H 0.602543 -0.014836 0.911933 0.036 Uiso 1 1 calc R U . . .
C19 C 0.6716(5) 0.0767(2) 0.8945(4) 0.0371(11) Uani 1 1 d . . . . .
H19 H 0.701016 0.086606 0.996434 0.045 Uiso 1 1 calc R U . . .
N31 N 0.1716(6) 0.1134(2) 1.0113(5) 0.0745(14) Uani 1 1 d . . . . .
C31 C 0.1623(6) 0.1101(2) 0.8890(6) 0.0460(12) Uani 1 1 d . . . . .
C32 C 0.1434(5) 0.1028(2) 0.7312(5) 0.0392(11) Uani 1 1 d . . . . .
H32A H 0.253121 0.109438 0.690307 0.047 Uiso 1 1 calc R U . . .
H32B H 0.065247 0.135907 0.687947 0.047 Uiso 1 1 calc R U . . .
C33 C 0.0773(5) 0.03698(18) 0.6861(4) 0.0334(10) Uani 1 1 d . . . . .
H33A H 0.161377 0.004124 0.719812 0.040 Uiso 1 1 calc R U . . .
H33B H -0.025903 0.028348 0.736362 0.040 Uiso 1 1 calc R U . . .
C34 C 0.0399(5) 0.03157(18) 0.5234(4) 0.0317(10) Uani 1 1 d . . . . .
H34A H 0.145254 0.036602 0.474020 0.038 Uiso 1 1 calc R U . . .
H34B H -0.036090 0.066969 0.488793 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.408(2) . ?
S11 O12 1.427(2) . ?
S11 N12 1.587(3) . ?
S11 C14 1.720(4) . ?
S12 C19 1.707(4) . ?
S12 C17 1.713(4) . ?
N11 C11 1.340(4) . ?
N11 H10 0.83(2) . ?
N11 H11 0.83(2) . ?
N12 C17 1.287(4) . ?
N13 C17 1.325(4) . ?
N13 C18 1.347(4) . ?
N13 H17 0.94(4) . ?
C11 C16 1.376(5) . ?
C11 C12 1.380(5) . ?
C12 C13 1.354(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(5) . ?
C15 C16 1.364(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.305(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C31 1.098(6) . ?
C31 C32 1.423(6) . ?
C32 C33 1.512(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.474(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C34 1.507(7) 3_556 ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.74(15) . . ?
O11 S11 N12 103.13(15) . . ?
O12 S11 N12 111.78(15) . . ?
O11 S11 C14 108.93(16) . . ?
O12 S11 C14 108.28(16) . . ?
N12 S11 C14 106.37(15) . . ?
C19 S12 C17 89.7(2) . . ?
C11 N11 H10 123(2) . . ?
C11 N11 H11 119(2) . . ?
H10 N11 H11 112.7(18) . . ?
C17 N12 S11 121.2(3) . . ?
C17 N13 C18 114.7(3) . . ?
C17 N13 H17 120(2) . . ?
C18 N13 H17 125(2) . . ?
N11 C11 C16 121.3(3) . . ?
N11 C11 C12 120.5(3) . . ?
C16 C11 C12 118.1(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 S11 121.3(3) . . ?
C13 C14 S11 119.1(3) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N12 C17 N13 119.6(3) . . ?
N12 C17 S12 130.1(3) . . ?
N13 C17 S12 110.3(3) . . ?
C19 C18 N13 113.0(4) . . ?
C19 C18 H18 123.5 . . ?
N13 C18 H18 123.5 . . ?
C18 C19 S12 112.3(3) . . ?
C18 C19 H19 123.9 . . ?
S12 C19 H19 123.9 . . ?
N31 C31 C32 176.6(5) . . ?
C31 C32 C33 111.8(4) . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C34 C33 C32 112.0(3) . . ?
C34 C33 H33A 109.2 . . ?
C32 C33 H33A 109.2 . . ?
C34 C33 H33B 109.2 . . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C33 C34 C34 113.0(4) . 3_556 ?
C33 C34 H34A 109.0 . . ?
C34 C34 H34A 109.0 3_556 . ?
C33 C34 H34B 109.0 . . ?
C34 C34 H34B 109.0 3_556 . ?
H34A C34 H34B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 167.4(2) . . . . ?
O12 S11 N12 C17 40.0(3) . . . . ?
C14 S11 N12 C17 -78.0(3) . . . . ?
N11 C11 C12 C13 179.8(3) . . . . ?
C16 C11 C12 C13 2.2(5) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C12 C13 C14 S11 174.5(3) . . . . ?
O11 S11 C14 C15 -146.3(3) . . . . ?
O12 S11 C14 C15 -17.1(3) . . . . ?
N12 S11 C14 C15 103.2(3) . . . . ?
O11 S11 C14 C13 39.0(3) . . . . ?
O12 S11 C14 C13 168.2(3) . . . . ?
N12 S11 C14 C13 -71.5(3) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
S11 C14 C15 C16 -174.1(3) . . . . ?
C14 C15 C16 C11 0.6(5) . . . . ?
N11 C11 C16 C15 -179.6(3) . . . . ?
C12 C11 C16 C15 -1.9(5) . . . . ?
S11 N12 C17 N13 174.8(2) . . . . ?
S11 N12 C17 S12 -4.8(4) . . . . ?
C18 N13 C17 N12 179.9(3) . . . . ?
C18 N13 C17 S12 -0.5(4) . . . . ?
C19 S12 C17 N12 179.3(3) . . . . ?
C19 S12 C17 N13 -0.3(3) . . . . ?
C17 N13 C18 C19 1.3(4) . . . . ?
N13 C18 C19 S12 -1.5(4) . . . . ?
C17 S12 C19 C18 1.1(3) . . . . ?
C31 C32 C33 C34 173.7(3) . . . . ?
C32 C33 C34 C34 -175.1(4) . . . 3_556 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.83(2) 2.22(2) 2.993(4) 155(3) 4_566 yes
N11 H11 O12 0.83(2) 2.21(3) 2.966(4) 152(3) 1_455 yes
N13 H17 O11 0.94(4) 2.60(4) 3.265(4) 128(3) 3_656 yes
N13 H17 N12 0.94(4) 1.87(4) 2.800(4) 170(4) 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_32
_database_code_depnum_ccdc_archive 'CCDC 2120794'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 5n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, pentanenitrile (1:1) solvate'
_chemical_name_common            'Sulfathiazole, valeronitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C5 H9 N'
_chemical_formula_sum            'C14 H18 N4 O2 S2'
_chemical_formula_weight         338.44
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4758(3)
_cell_length_b                   20.7179(9)
_cell_length_c                   9.6108(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.840(2)
_cell_angle_gamma                90
_cell_volume                     1671.89(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8262
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.330
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11011
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.585
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2937
_reflns_number_gt                1907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  5n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.21      46     61     75.4     2.72     185.3   35.21  0.0683  0.0308
3.21 - 2.24     106    111     95.5     3.42      79.4   24.74  0.0670  0.0304
2.24 - 1.80     157    157    100.0     3.92      38.6   19.73  0.0817  0.0358
1.80 - 1.58     145    145    100.0     4.06      31.0   16.99  0.0860  0.0413
1.58 - 1.43     161    161    100.0     4.26      22.1   14.53  0.1067  0.0491
1.43 - 1.33     152    152    100.0     4.09      23.0   12.43  0.1182  0.0542
1.33 - 1.25     157    157    100.0     4.32      17.2   11.05  0.1284  0.0629
1.25 - 1.19     147    147    100.0     4.18      18.6   10.51  0.1214  0.0691
1.19 - 1.14     151    151    100.0     4.34      17.7    9.54  0.1444  0.0735
1.14 - 1.10     138    138    100.0     4.36      14.4    8.94  0.1422  0.0821
1.10 - 1.05     198    198    100.0     4.33      10.3    7.21  0.1803  0.1078
1.05 - 1.02     149    149    100.0     4.07       8.7    6.34  0.2045  0.1307
1.02 - 0.99     153    153    100.0     4.17       6.8    5.36  0.2109  0.1597
0.99 - 0.97     116    116    100.0     3.82       6.6    4.68  0.2222  0.1851
0.97 - 0.94     196    196    100.0     3.43       5.0    3.34  0.2632  0.2692
0.94 - 0.92     137    137    100.0     3.11       5.9    3.49  0.2471  0.2567
0.92 - 0.90     171    171    100.0     2.98       4.8    2.84  0.2807  0.3244
0.90 - 0.88     166    166    100.0     2.96       4.3    2.63  0.2982  0.3474
0.88 - 0.87      86     86    100.0     2.67       4.1    2.27  0.3160  0.4098
0.87 - 0.85     191    193     99.0     2.35       3.4    1.69  0.3525  0.5306
0.85 - 0.84     108    109     99.1     2.24       3.1    1.39  0.3966  0.6253
#------------------------------------------------------------------------------
0.94 - 0.84     859    862     99.7     2.73       4.3    2.41  0.2996  0.3867
 Inf - 0.84    3031   3054     99.2     3.66      18.0    8.72  0.1193  0.0806
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2937
_refine_ls_number_parameters     233
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.068

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.50942(9) 0.14980(4) 0.42501(9) 0.0294(2) Uani 1 1 d . . . . .
S12 S 0.62302(10) 0.13518(4) 0.76796(9) 0.0386(3) Uani 1 1 d . . . . .
O11 O 0.4898(3) 0.13200(10) 0.2786(2) 0.0364(6) Uani 1 1 d . . . . .
O12 O 0.6428(2) 0.19078(10) 0.4765(2) 0.0398(6) Uani 1 1 d . . . . .
N11 N -0.0818(3) 0.27624(15) 0.5465(3) 0.0392(8) Uani 1 1 d D . . . .
H10 H -0.081(3) 0.3018(16) 0.621(3) 0.056(12) Uiso 1 1 d D . . . .
H11 H -0.176(3) 0.2566(16) 0.525(3) 0.057(12) Uiso 1 1 d D . . . .
N12 N 0.5175(3) 0.08150(12) 0.5048(3) 0.0262(6) Uani 1 1 d . . . . .
N13 N 0.5746(3) 0.01793(14) 0.7023(3) 0.0296(7) Uani 1 1 d . . . . .
H17 H 0.550(4) -0.0135(17) 0.653(4) 0.042(11) Uiso 1 1 d . . . . .
C11 C 0.0561(3) 0.24715(15) 0.5192(3) 0.0274(7) Uani 1 1 d . . . . .
C12 C 0.0516(3) 0.19675(15) 0.4217(3) 0.0295(7) Uani 1 1 d . . . . .
H12 H -0.048370 0.182301 0.375360 0.035 Uiso 1 1 calc R U . . .
C13 C 0.1890(3) 0.16771(15) 0.3916(3) 0.0279(7) Uani 1 1 d . . . . .
H13 H 0.183782 0.133533 0.325234 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3368(3) 0.18889(14) 0.4596(3) 0.0259(7) Uani 1 1 d . . . . .
C15 C 0.3430(3) 0.23954(14) 0.5552(3) 0.0273(7) Uani 1 1 d . . . . .
H15 H 0.443236 0.254310 0.600157 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2051(3) 0.26860(14) 0.5855(3) 0.0272(7) Uani 1 1 d . . . . .
H16 H 0.210841 0.303088 0.651092 0.033 Uiso 1 1 calc R U . . .
C17 C 0.5661(3) 0.07622(15) 0.6422(3) 0.0264(7) Uani 1 1 d . . . . .
C18 C 0.6229(4) 0.01744(17) 0.8452(3) 0.0372(8) Uani 1 1 d . . . . .
H18 H 0.634278 -0.020851 0.900008 0.045 Uiso 1 1 calc R U . . .
C19 C 0.6522(4) 0.07653(18) 0.8984(4) 0.0454(9) Uani 1 1 d . . . . .
H19 H 0.684697 0.085343 0.995110 0.054 Uiso 1 1 calc R U . . .
N31 N 0.0408(4) 0.10910(17) 1.0787(4) 0.0549(9) Uani 1 1 d . . . . .
C31 C 0.0629(4) 0.12571(17) 0.9715(4) 0.0410(9) Uani 1 1 d D . . . .
C32 C 0.0932(5) 0.14477(15) 0.8299(4) 0.0469(10) Uani 0.629(9) 1 d D . P A 1
H32A H 0.161488 0.183725 0.837163 0.056 Uiso 0.629(9) 1 calc R U P A 1
H32B H -0.009140 0.156048 0.772561 0.056 Uiso 0.629(9) 1 calc R U P A 1
C33 C 0.1744(7) 0.0913(2) 0.7558(6) 0.0386(18) Uani 0.629(9) 1 d D . P A 1
H33A H 0.206450 0.108396 0.667579 0.046 Uiso 0.629(9) 1 calc R U P A 1
H33B H 0.271699 0.076964 0.816700 0.046 Uiso 0.629(9) 1 calc R U P A 1
C34 C 0.0635(8) 0.0344(3) 0.7226(7) 0.049(2) Uani 0.629(9) 1 d D . P A 1
H34A H -0.029280 0.047794 0.654847 0.059 Uiso 0.629(9) 1 calc R U P A 1
H34B H 0.023703 0.019756 0.809558 0.059 Uiso 0.629(9) 1 calc R U P A 1
C35 C 0.1507(5) -0.02229(18) 0.6596(5) 0.0613(12) Uani 0.629(9) 1 d D . P A 1
H35A H 0.197044 -0.006972 0.577581 0.092 Uiso 0.629(9) 1 calc R U P A 1
H35B H 0.074590 -0.057001 0.631045 0.092 Uiso 0.629(9) 1 calc R U P A 1
H35C H 0.235520 -0.038622 0.730338 0.092 Uiso 0.629(9) 1 calc R U P A 1
C32A C 0.0932(5) 0.14477(15) 0.8299(4) 0.0469(10) Uani 0.371(9) 1 d D . P A 2
H32C H 0.205076 0.159128 0.833321 0.056 Uiso 0.371(9) 1 calc R U P A 2
H32D H 0.022934 0.181270 0.795888 0.056 Uiso 0.371(9) 1 calc R U P A 2
C33A C 0.0611(14) 0.0865(4) 0.7270(7) 0.047(4) Uani 0.371(9) 1 d D . P A 2
H33C H -0.051688 0.073133 0.721367 0.056 Uiso 0.371(9) 1 calc R U P A 2
H33D H 0.080815 0.099735 0.631851 0.056 Uiso 0.371(9) 1 calc R U P A 2
C34A C 0.1691(12) 0.0297(3) 0.7769(9) 0.040(3) Uani 0.371(9) 1 d D . P A 2
H34C H 0.138245 0.011579 0.864591 0.048 Uiso 0.371(9) 1 calc R U P A 2
H34D H 0.281242 0.044194 0.795909 0.048 Uiso 0.371(9) 1 calc R U P A 2
C35A C 0.1507(5) -0.02229(18) 0.6596(5) 0.0613(12) Uani 0.371(9) 1 d D . P A 2
H35D H 0.042864 -0.040312 0.649897 0.092 Uiso 0.371(9) 1 calc R U P A 2
H35E H 0.228552 -0.056808 0.684254 0.092 Uiso 0.371(9) 1 calc R U P A 2
H35F H 0.169107 -0.002580 0.570499 0.092 Uiso 0.371(9) 1 calc R U P A 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.442(2) . ?
S11 O12 1.446(2) . ?
S11 N12 1.606(3) . ?
S11 C14 1.743(3) . ?
S12 C19 1.740(4) . ?
S12 C17 1.740(3) . ?
N11 C11 1.372(4) . ?
N11 H10 0.89(2) . ?
N11 H11 0.89(2) . ?
N12 C17 1.333(4) . ?
N13 C17 1.336(4) . ?
N13 C18 1.378(4) . ?
N13 H17 0.82(3) . ?
C11 C12 1.400(4) . ?
C11 C16 1.407(4) . ?
C12 C13 1.377(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.402(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(4) . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.337(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C31 1.126(4) . ?
C31 C32A 1.473(5) . ?
C31 C32 1.473(5) . ?
C32 C33 1.530(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.515(7) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.553(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C32A C33A 1.561(7) . ?
C32A H32C 0.9900 . ?
C32A H32D 0.9900 . ?
C33A C34A 1.527(8) . ?
C33A H33C 0.9900 . ?
C33A H33D 0.9900 . ?
C34A C35A 1.552(7) . ?
C34A H34C 0.9900 . ?
C34A H34D 0.9900 . ?
C35A H35D 0.9800 . ?
C35A H35E 0.9800 . ?
C35A H35F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.69(13) . . ?
O11 S11 N12 103.41(13) . . ?
O12 S11 N12 111.94(13) . . ?
O11 S11 C14 108.46(14) . . ?
O12 S11 C14 107.42(14) . . ?
N12 S11 C14 107.48(14) . . ?
C19 S12 C17 90.51(16) . . ?
C11 N11 H10 120(2) . . ?
C11 N11 H11 121(2) . . ?
H10 N11 H11 111.4(16) . . ?
C17 N12 S11 122.1(2) . . ?
C17 N13 C18 115.4(3) . . ?
C17 N13 H17 118(2) . . ?
C18 N13 H17 126(2) . . ?
N11 C11 C12 120.6(3) . . ?
N11 C11 C16 120.7(3) . . ?
C12 C11 C16 118.7(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 S11 121.3(2) . . ?
C13 C14 S11 119.0(2) . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
N12 C17 N13 119.6(3) . . ?
N12 C17 S12 130.5(2) . . ?
N13 C17 S12 109.9(2) . . ?
C19 C18 N13 112.9(3) . . ?
C19 C18 H18 123.5 . . ?
N13 C18 H18 123.5 . . ?
C18 C19 S12 111.3(3) . . ?
C18 C19 H19 124.4 . . ?
S12 C19 H19 124.4 . . ?
N31 C31 C32A 177.7(4) . . ?
N31 C31 C32 177.7(4) . . ?
C31 C32 C33 112.5(3) . . ?
C31 C32 H32A 109.1 . . ?
C33 C32 H32A 109.1 . . ?
C31 C32 H32B 109.1 . . ?
C33 C32 H32B 109.1 . . ?
H32A C32 H32B 107.8 . . ?
C34 C33 C32 110.9(4) . . ?
C34 C33 H33A 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
C33 C34 C35 110.8(5) . . ?
C33 C34 H34A 109.5 . . ?
C35 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C31 C32A C33A 109.9(4) . . ?
C31 C32A H32C 109.7 . . ?
C33A C32A H32C 109.7 . . ?
C31 C32A H32D 109.7 . . ?
C33A C32A H32D 109.7 . . ?
H32C C32A H32D 108.2 . . ?
C34A C33A C32A 110.6(6) . . ?
C34A C33A H33C 109.5 . . ?
C32A C33A H33C 109.5 . . ?
C34A C33A H33D 109.5 . . ?
C32A C33A H33D 109.5 . . ?
H33C C33A H33D 108.1 . . ?
C33A C34A C35A 108.1(6) . . ?
C33A C34A H34C 110.1 . . ?
C35A C34A H34C 110.1 . . ?
C33A C34A H34D 110.1 . . ?
C35A C34A H34D 110.1 . . ?
H34C C34A H34D 108.4 . . ?
C34A C35A H35D 109.5 . . ?
C34A C35A H35E 109.5 . . ?
H35D C35A H35E 109.5 . . ?
C34A C35A H35F 109.5 . . ?
H35D C35A H35F 109.5 . . ?
H35E C35A H35F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 166.6(2) . . . . ?
O12 S11 N12 C17 38.9(3) . . . . ?
C14 S11 N12 C17 -78.8(2) . . . . ?
N11 C11 C12 C13 179.0(3) . . . . ?
C16 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C12 C13 C14 S11 177.8(2) . . . . ?
O11 S11 C14 C15 -144.7(2) . . . . ?
O12 S11 C14 C15 -16.6(3) . . . . ?
N12 S11 C14 C15 104.1(3) . . . . ?
O11 S11 C14 C13 36.6(3) . . . . ?
O12 S11 C14 C13 164.8(2) . . . . ?
N12 S11 C14 C13 -74.6(3) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
S11 C14 C15 C16 -177.7(2) . . . . ?
C14 C15 C16 C11 -0.1(5) . . . . ?
N11 C11 C16 C15 -178.9(3) . . . . ?
C12 C11 C16 C15 -0.8(4) . . . . ?
S11 N12 C17 N13 -178.2(2) . . . . ?
S11 N12 C17 S12 2.6(4) . . . . ?
C18 N13 C17 N12 -178.7(3) . . . . ?
C18 N13 C17 S12 0.6(3) . . . . ?
C19 S12 C17 N12 178.2(3) . . . . ?
C19 S12 C17 N13 -1.1(2) . . . . ?
C17 N13 C18 C19 0.3(4) . . . . ?
N13 C18 C19 S12 -1.2(4) . . . . ?
C17 S12 C19 C18 1.3(3) . . . . ?
C31 C32 C33 C34 67.4(6) . . . . ?
C32 C33 C34 C35 -174.9(4) . . . . ?
C31 C32A C33A C34A -59.7(9) . . . . ?
C32A C33A C34A C35A -171.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.89(2) 2.07(3) 2.931(4) 162(3) 4_566 yes
N11 H11 O12 0.89(2) 2.06(3) 2.934(3) 166(3) 1_455 yes
N13 H17 O11 0.82(3) 2.58(3) 3.163(4) 130(3) 3_656 yes
N13 H17 N12 0.82(3) 2.09(4) 2.896(4) 169(3) 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24
_database_code_depnum_ccdc_archive 'CCDC 2120785'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 25o
#===============================================================================
# start Validation Reply Form
_vrf_PLAT029_24                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.923 Why?  
RESPONSE: The data are measured with a point-detector instrument. The missing
data are uniformly distributed over the resolution shells beyond ca 1.4 
angstrom and there is no systematic omission of high-angle data (for example).
There is no indication of any adverse effect on the refined structure.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, cyclopentanol (1:1) solvate'
_chemical_name_common            'Sulfathiazole, cyclopentanol solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C5 H10 O'
_chemical_formula_sum            'C14 H19 N3 O3 S2'
_chemical_formula_weight         341.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.705(4)
_cell_length_b                   11.385(2)
_cell_length_c                   14.136(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.02(3)
_cell_angle_gamma                90
_cell_volume                     3291.0(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      4.45
_cell_measurement_theta_max      66.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.073
_shelx_estimated_absorpt_T_min   0.459
_shelx_estimated_absorpt_T_max   0.749
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            2756
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.445
_diffrn_reflns_theta_max         66.546
_diffrn_reflns_theta_full        66.546
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.923
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.923
_reflns_number_total             2682
_reflns_number_gt                1775
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  25o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.73      42     42    100.0     1.12     106.9   33.40  0.0232  0.0125
3.73 - 2.41      99     99    100.0     1.08      48.6   24.63  0.0279  0.0238
2.41 - 1.89     145    147     98.6     1.02      19.4   20.33  0.0127  0.0358
1.89 - 1.64     136    144     94.4     1.00      17.8   19.91  0.0184  0.0377
1.64 - 1.49     137    142     96.5     0.99      14.8   16.58  0.0729  0.0455
1.49 - 1.38     139    144     96.5     1.00       9.0   11.86  0.0628  0.0729
1.38 - 1.28     154    171     90.1     0.93      10.6   12.96  0.0353  0.0645
1.28 - 1.22     131    134     97.8     1.00       7.6   10.43  0.1001  0.0881
1.22 - 1.16     146    159     91.8     0.94       8.2   10.58  0.0431  0.0878
1.16 - 1.12     131    137     95.6     1.00       6.1    8.09  0.0814  0.1123
1.12 - 1.07     168    184     91.3     0.94       5.3    7.81  0.0863  0.1259
1.07 - 1.04     123    138     89.1     0.91       4.7    6.87  0.0484  0.1440
1.04 - 1.01     127    139     91.4     0.92       3.4    5.43  0.0952  0.1960
1.01 - 0.98     154    171     90.1     0.91       2.7    4.56  0.0302  0.2463
0.98 - 0.95     161    183     88.0     0.89       2.2    3.98  0.0693  0.3097
0.95 - 0.93     126    144     87.5     0.91       2.5    4.49  0.1811  0.2678
0.93 - 0.91     126    144     87.5     0.90       1.9    3.90  0.0551  0.3074
0.91 - 0.89     155    178     87.1     0.88       1.5    3.13  0.7241  0.4267
0.89 - 0.87     153    170     90.0     0.93       1.4    2.97  0.2890  0.4602
0.87 - 0.85     183    201     91.0     0.93       1.1    2.45  0.4515  0.5512
0.85 - 0.84      65     97     67.0     0.67       1.0    1.99  0.0000  0.7122
#------------------------------------------------------------------------------
0.94 - 0.84     743    862     86.2     0.88       1.5    3.11  0.1744  0.4172
 Inf - 0.84    2801   3068     91.3     0.94       9.4    9.33  0.0339  0.0736
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2682
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.061

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.59904(4) 0.78197(7) 0.58435(6) 0.0372(2) Uani 1 1 d . . . . .
S12 S 0.65226(4) 0.90317(9) 0.39861(7) 0.0551(3) Uani 1 1 d . . . . .
O11 O 0.55449(12) 0.7467(2) 0.64817(16) 0.0504(7) Uani 1 1 d . . . . .
O12 O 0.66399(11) 0.8180(2) 0.62781(17) 0.0509(7) Uani 1 1 d . . . . .
N11 N 0.62701(19) 0.3988(3) 0.3134(3) 0.0736(11) Uani 1 1 d . . . . .
H10 H 0.592967 0.364120 0.283291 0.110 Uiso 1 1 calc R U . . .
H11 H 0.665351 0.378047 0.303620 0.110 Uiso 1 1 calc R U . . .
N12 N 0.56114(12) 0.8869(2) 0.52368(18) 0.0357(6) Uani 1 1 d . . . . .
N13 N 0.55453(13) 1.0302(2) 0.40619(19) 0.0410(7) Uani 1 1 d . . . . .
H17 H 0.519678 1.059810 0.422537 0.061 Uiso 1 1 calc R U . . .
C11 C 0.62020(19) 0.4864(3) 0.3765(3) 0.0478(9) Uani 1 1 d . . . . .
C12 C 0.55887(18) 0.5228(3) 0.3945(3) 0.0533(10) Uani 1 1 d . . . . .
H12 H 0.521441 0.485938 0.363203 0.064 Uiso 1 1 calc R U . . .
C13 C 0.55311(17) 0.6115(3) 0.4573(3) 0.0474(9) Uani 1 1 d . . . . .
H13 H 0.511757 0.635226 0.467338 0.057 Uiso 1 1 calc R U . . .
C14 C 0.60781(15) 0.6667(3) 0.5063(2) 0.0330(7) Uani 1 1 d . . . . .
C15 C 0.66948(16) 0.6311(3) 0.4906(2) 0.0416(9) Uani 1 1 d . . . . .
H15 H 0.706652 0.667551 0.523087 0.050 Uiso 1 1 calc R U . . .
C16 C 0.67546(18) 0.5419(3) 0.4268(3) 0.0501(10) Uani 1 1 d . . . . .
H16 H 0.716873 0.518120 0.416977 0.060 Uiso 1 1 calc R U . . .
C17 C 0.58498(15) 0.9381(3) 0.4516(2) 0.0344(8) Uani 1 1 d . . . . .
C18 C 0.58227(17) 1.0749(3) 0.3318(3) 0.0485(9) Uani 1 1 d . . . . .
H18 H 0.565683 1.139248 0.295395 0.058 Uiso 1 1 calc R U . . .
C19 C 0.63510(18) 1.0165(3) 0.3174(3) 0.0544(10) Uani 1 1 d . . . . .
H19 H 0.659805 1.034281 0.269716 0.065 Uiso 1 1 calc R U . . .
O30 O 0.75795(13) 0.6825(2) 0.7610(2) 0.0662(8) Uani 1 1 d . . . . .
H30 H 0.730646 0.721778 0.722279 0.099 Uiso 1 1 d R U . . .
C30 C 0.7766(2) 0.7497(4) 0.8476(3) 0.0724(13) Uani 1 1 d . . . . .
H30A H 0.738576 0.766549 0.878756 0.087 Uiso 1 1 calc R U . . .
C31 C 0.8104(2) 0.8604(4) 0.8269(4) 0.0862(15) Uani 1 1 d . . . . .
H31A H 0.793974 0.888326 0.762820 0.103 Uiso 1 1 calc R U . . .
H31B H 0.803840 0.921155 0.872531 0.103 Uiso 1 1 calc R U . . .
C32 C 0.8801(2) 0.8296(5) 0.8356(5) 0.112(2) Uani 1 1 d . . . . .
H32A H 0.906890 0.893507 0.865342 0.135 Uiso 1 1 calc R U . . .
H32B H 0.891700 0.815089 0.772795 0.135 Uiso 1 1 calc R U . . .
C33 C 0.8909(3) 0.7222(5) 0.8956(5) 0.131(3) Uani 1 1 d . . . . .
H33A H 0.912570 0.662684 0.862848 0.157 Uiso 1 1 calc R U . . .
H33B H 0.918322 0.740256 0.955912 0.157 Uiso 1 1 calc R U . . .
C34 C 0.8273(2) 0.6792(5) 0.9129(3) 0.0911(17) Uani 1 1 d . . . . .
H34A H 0.822370 0.690826 0.979405 0.109 Uiso 1 1 calc R U . . .
H34B H 0.822715 0.596105 0.898147 0.109 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.444(2) . ?
S11 O12 1.447(2) . ?
S11 N12 1.602(3) . ?
S11 C14 1.742(3) . ?
S12 C19 1.727(4) . ?
S12 C17 1.729(3) . ?
N11 C11 1.360(4) . ?
N11 H10 0.8600 . ?
N11 H11 0.8600 . ?
N12 C17 1.333(4) . ?
N13 C17 1.336(4) . ?
N13 C18 1.372(4) . ?
N13 H17 0.8600 . ?
C11 C12 1.397(5) . ?
C11 C16 1.400(5) . ?
C12 C13 1.362(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(4) . ?
C15 C16 1.377(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.322(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O30 C30 1.444(5) . ?
O30 H30 0.8500 . ?
C30 C31 1.493(6) . ?
C30 C34 1.515(6) . ?
C30 H30A 0.9800 . ?
C31 C32 1.470(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.485(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.461(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.09(15) . . ?
O11 S11 N12 103.55(14) . . ?
O12 S11 N12 111.12(15) . . ?
O11 S11 C14 109.05(15) . . ?
O12 S11 C14 107.46(15) . . ?
N12 S11 C14 108.28(14) . . ?
C19 S12 C17 91.18(17) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 121.7(2) . . ?
C17 N13 C18 115.9(3) . . ?
C17 N13 H17 122.1 . . ?
C18 N13 H17 122.1 . . ?
N11 C11 C12 121.9(4) . . ?
N11 C11 C16 120.2(4) . . ?
C12 C11 C16 117.9(3) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 S11 120.1(2) . . ?
C15 C14 S11 120.7(2) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N12 C17 N13 120.5(3) . . ?
N12 C17 S12 130.6(2) . . ?
N13 C17 S12 108.9(2) . . ?
C19 C18 N13 112.8(3) . . ?
C19 C18 H18 123.6 . . ?
N13 C18 H18 123.6 . . ?
C18 C19 S12 111.2(3) . . ?
C18 C19 H19 124.4 . . ?
S12 C19 H19 124.4 . . ?
C30 O30 H30 109.2 . . ?
O30 C30 C31 110.7(4) . . ?
O30 C30 C34 107.7(4) . . ?
C31 C30 C34 105.4(4) . . ?
O30 C30 H30A 111.0 . . ?
C31 C30 H30A 111.0 . . ?
C34 C30 H30A 111.0 . . ?
C32 C31 C30 105.5(4) . . ?
C32 C31 H31A 110.7 . . ?
C30 C31 H31A 110.7 . . ?
C32 C31 H31B 110.7 . . ?
C30 C31 H31B 110.7 . . ?
H31A C31 H31B 108.8 . . ?
C31 C32 C33 107.6(4) . . ?
C31 C32 H32A 110.2 . . ?
C33 C32 H32A 110.2 . . ?
C31 C32 H32B 110.2 . . ?
C33 C32 H32B 110.2 . . ?
H32A C32 H32B 108.5 . . ?
C34 C33 C32 108.3(4) . . ?
C34 C33 H33A 110.0 . . ?
C32 C33 H33A 110.0 . . ?
C34 C33 H33B 110.0 . . ?
C32 C33 H33B 110.0 . . ?
H33A C33 H33B 108.4 . . ?
C33 C34 C30 106.0(4) . . ?
C33 C34 H34A 110.5 . . ?
C30 C34 H34A 110.5 . . ?
C33 C34 H34B 110.5 . . ?
C30 C34 H34B 110.5 . . ?
H34A C34 H34B 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 -175.4(2) . . . . ?
O12 S11 N12 C17 58.1(3) . . . . ?
C14 S11 N12 C17 -59.7(3) . . . . ?
N11 C11 C12 C13 -179.4(4) . . . . ?
C16 C11 C12 C13 1.6(6) . . . . ?
C11 C12 C13 C14 -1.1(6) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C12 C13 C14 S11 178.7(3) . . . . ?
O11 S11 C14 C13 49.6(3) . . . . ?
O12 S11 C14 C13 177.5(3) . . . . ?
N12 S11 C14 C13 -62.4(3) . . . . ?
O11 S11 C14 C15 -132.1(3) . . . . ?
O12 S11 C14 C15 -4.2(3) . . . . ?
N12 S11 C14 C15 115.9(3) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
S11 C14 C15 C16 -178.3(3) . . . . ?
C14 C15 C16 C11 0.5(5) . . . . ?
N11 C11 C16 C15 179.7(4) . . . . ?
C12 C11 C16 C15 -1.3(6) . . . . ?
S11 N12 C17 N13 -175.7(2) . . . . ?
S11 N12 C17 S12 6.5(4) . . . . ?
C18 N13 C17 N12 -178.7(3) . . . . ?
C18 N13 C17 S12 -0.4(4) . . . . ?
C19 S12 C17 N12 178.1(3) . . . . ?
C19 S12 C17 N13 0.1(2) . . . . ?
C17 N13 C18 C19 0.7(5) . . . . ?
N13 C18 C19 S12 -0.6(4) . . . . ?
C17 S12 C19 C18 0.3(3) . . . . ?
O30 C30 C31 C32 -88.7(5) . . . . ?
C34 C30 C31 C32 27.5(6) . . . . ?
C30 C31 C32 C33 -21.6(7) . . . . ?
C31 C32 C33 C34 7.2(8) . . . . ?
C32 C33 C34 C30 10.0(7) . . . . ?
O30 C30 C34 C33 95.0(6) . . . . ?
C31 C30 C34 C33 -23.2(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.86 2.32 3.059(4) 143.6 6_565 yes
N11 H11 O30 0.86 2.21 3.063(5) 173.0 6_565 yes
N13 H17 N12 0.86 2.04 2.890(4) 172.0 5_676 yes
O30 H30 O12 0.85 2.08 2.926(4) 179.9 . yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_26
_database_code_depnum_ccdc_archive 'CCDC 2120792'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 27o
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, triethyl phosphate (1:1) solvate'
_chemical_name_common            'Sulfathiazole, triethyl phosphate solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C6 H15 O4 P'
_chemical_formula_sum            'C15 H24 N3 O6 P S2'
_chemical_formula_weight         437.46
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   19.639(4)
_cell_length_b                   8.864(2)
_cell_length_c                   24.612(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4284.5(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19195
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.358
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19195
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.074
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4688
_reflns_number_gt                3458
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_max     0.920
_reflns_Friedel_fraction_full    0.988

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  27o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.59      41     41    100.0     6.41     309.6   35.92  0.0180  0.0311
3.59 - 2.24      95     95    100.0     8.56      85.5   41.99  0.0284  0.0200
2.24 - 1.75     136    136    100.0     8.90      46.1   39.65  0.0397  0.0206
1.75 - 1.50     139    139    100.0     9.34      26.2   30.82  0.0485  0.0241
1.50 - 1.36     139    139    100.0     9.22      21.9   27.99  0.0540  0.0278
1.36 - 1.25     143    143    100.0     9.34      22.2   24.51  0.0610  0.0306
1.25 - 1.18     120    120    100.0     9.41      21.9   24.51  0.0674  0.0333
1.18 - 1.11     151    151    100.0     9.43      14.5   18.12  0.0873  0.0431
1.11 - 1.06     139    139    100.0     9.39      13.1   17.10  0.1004  0.0480
1.06 - 1.02     125    125    100.0     9.46      10.0   14.72  0.1204  0.0586
1.02 - 0.98     145    145    100.0     9.05       6.8   10.67  0.1557  0.0794
0.98 - 0.95     130    130    100.0     9.06       6.1    9.71  0.1677  0.0902
0.95 - 0.92     156    156    100.0     8.42       5.3    7.88  0.1988  0.1085
0.92 - 0.90      98     98    100.0     7.72       6.4    7.53  0.1883  0.1070
0.90 - 0.87     181    181    100.0     6.49       5.1    5.23  0.2438  0.1572
0.87 - 0.85     144    144    100.0     6.06       3.9    4.48  0.2746  0.2112
0.85 - 0.83     142    142    100.0     5.48       3.9    3.70  0.3184  0.2559
0.83 - 0.81     156    156    100.0     4.22       2.9    2.18  0.4269  0.4240
0.81 - 0.80      83     90     92.2     3.47       3.2    2.16  0.5304  0.4389
0.80 - 0.78     169    188     89.9     2.64       3.0    1.73  0.5018  0.5433
0.78 - 0.77      79     98     80.6     1.96       2.7    1.33  0.5608  0.6622
#------------------------------------------------------------------------------
0.87 - 0.77     773    818     94.5     4.04       3.3    2.70  0.3778  0.3859
 Inf - 0.77    2711   2756     98.4     7.36      19.0   14.84  0.0732  0.0530
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_abs_structure_details 
;
Flack x determined using 1362 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_number_reflns         4688
_refine_ls_number_parameters     281
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.059

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.13265(5) 0.77791(9) 0.33781(4) 0.0242(2) Uani 1 1 d . . . . .
S12 S 0.18359(5) 1.13227(10) 0.35099(5) 0.0298(3) Uani 1 1 d . . . . .
O11 O 0.09309(14) 0.6525(2) 0.35694(12) 0.0304(7) Uani 1 1 d . . . . .
O12 O 0.19482(13) 0.8161(3) 0.36613(12) 0.0290(7) Uani 1 1 d . . . . .
N11 N 0.2019(3) 0.6490(6) 0.10794(18) 0.0651(15) Uani 1 1 d . . . . .
H10 H 0.177720 0.583819 0.089071 0.098 Uiso 1 1 calc R U . . .
H11 H 0.236737 0.695012 0.092795 0.098 Uiso 1 1 calc R U . . .
N12 N 0.08072(14) 0.9184(3) 0.33832(15) 0.0243(7) Uani 1 1 d . . . . .
N13 N 0.05668(15) 1.1720(3) 0.34318(15) 0.0253(7) Uani 1 1 d . . . . .
H17 H 0.012618 1.156030 0.340126 0.038 Uiso 1 1 calc R U . . .
C11 C 0.1850(3) 0.6792(6) 0.16142(19) 0.0436(13) Uani 1 1 d . . . . .
C12 C 0.1303(3) 0.6089(6) 0.1867(2) 0.0454(13) Uani 1 1 d . . . . .
H12 H 0.103745 0.538085 0.166971 0.055 Uiso 1 1 calc R U . . .
C13 C 0.1142(2) 0.6404(5) 0.2397(2) 0.0381(11) Uani 1 1 d . . . . .
H13 H 0.076013 0.592559 0.256021 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1530(2) 0.7413(4) 0.26997(19) 0.0274(9) Uani 1 1 d . . . . .
C15 C 0.2085(2) 0.8128(5) 0.24487(18) 0.0328(10) Uani 1 1 d . . . . .
H15 H 0.235263 0.882619 0.264885 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2244(3) 0.7827(5) 0.19152(19) 0.0399(12) Uani 1 1 d . . . . .
H16 H 0.261988 0.831762 0.174911 0.048 Uiso 1 1 calc R U . . .
C17 C 0.10191(16) 1.0602(4) 0.34366(17) 0.0219(8) Uani 1 1 d . . . . .
C18 C 0.08396(18) 1.3146(4) 0.34782(18) 0.0287(10) Uani 1 1 d . . . . .
H18 H 0.057238 1.403941 0.348382 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1515(2) 1.3144(4) 0.3514(2) 0.0325(10) Uani 1 1 d . . . . .
H19 H 0.178648 1.402827 0.353894 0.039 Uiso 1 1 calc R U . . .
P31 P 0.10431(9) 0.2454(2) 0.06407(6) 0.0611(5) Uani 0.481(4) 1 d . . P A 1
O31 O 0.1142(4) 0.4239(8) 0.0499(3) 0.060(2) Uani 0.481(4) 1 d . . P A 1
O32 O 0.0413(4) 0.1884(9) 0.0427(3) 0.058(2) Uani 0.481(4) 1 d D . P A 1
O33 O 0.1080(5) 0.2432(7) 0.1275(3) 0.050(2) Uani 0.481(4) 1 d D . P A 1
O34 O 0.1644(5) 0.1564(9) 0.0438(3) 0.052(2) Uani 0.481(4) 1 d D . P A 1
C31 C -0.0235(4) 0.2632(11) 0.0340(4) 0.135(4) Uani 0.481(4) 1 d D . P A 1
H31A H -0.022294 0.359410 0.054339 0.162 Uiso 0.481(4) 1 calc R U P A 1
H31B H -0.059070 0.199831 0.051094 0.162 Uiso 0.481(4) 1 calc R U P A 1
C32 C -0.0462(7) 0.2972(13) -0.0202(4) 0.167(5) Uani 0.481(4) 1 d D . P A 1
H32A H -0.090608 0.347283 -0.018597 0.251 Uiso 0.481(4) 1 calc R U P A 1
H32B H -0.013138 0.364145 -0.037826 0.251 Uiso 0.481(4) 1 calc R U P A 1
H32C H -0.050148 0.203553 -0.041092 0.251 Uiso 0.481(4) 1 calc R U P A 1
C33 C 0.1002(4) 0.0832(7) 0.1523(2) 0.0713(19) Uani 0.481(4) 1 d D . P A 1
H33A H 0.063523 0.025018 0.134394 0.086 Uiso 0.481(4) 1 calc R U P A 1
H33B H 0.143319 0.025449 0.150697 0.086 Uiso 0.481(4) 1 calc R U P A 1
C34 C 0.0820(4) 0.1249(8) 0.2089(2) 0.080(2) Uani 0.481(4) 1 d D . P A 1
H34A H 0.075211 0.033163 0.230433 0.120 Uiso 0.481(4) 1 calc R U P A 1
H34B H 0.118885 0.184802 0.224878 0.120 Uiso 0.481(4) 1 calc R U P A 1
H34C H 0.039944 0.184377 0.208750 0.120 Uiso 0.481(4) 1 calc R U P A 1
C35 C 0.1698(4) 0.1042(8) -0.0142(2) 0.074(2) Uani 0.481(4) 1 d D . P A 1
H35A H 0.184567 0.188468 -0.037837 0.089 Uiso 0.481(4) 1 calc R U P A 1
H35B H 0.125131 0.067368 -0.027205 0.089 Uiso 0.481(4) 1 calc R U P A 1
C36 C 0.2214(4) -0.0210(10) -0.0156(3) 0.097(2) Uani 0.481(4) 1 d D . P A 1
H36A H 0.226281 -0.057976 -0.052899 0.146 Uiso 0.481(4) 1 calc R U P A 1
H36B H 0.265423 0.016894 -0.002646 0.146 Uiso 0.481(4) 1 calc R U P A 1
H36C H 0.206242 -0.103684 0.007939 0.146 Uiso 0.481(4) 1 calc R U P A 1
P31A P 0.10431(9) 0.2454(2) 0.06407(6) 0.0611(5) Uani 0.519(4) 1 d . . P A 2
O31A O 0.1586(4) 0.3228(9) 0.0776(3) 0.062(2) Uani 0.519(4) 1 d . . P A 2
O32A O 0.0478(4) 0.3085(11) 0.0302(4) 0.083(3) Uani 0.519(4) 1 d . . P A 2
O33A O 0.0621(4) 0.1525(10) 0.1115(3) 0.070(3) Uani 0.519(4) 1 d . . P A 2
O34A O 0.1218(5) 0.0805(9) 0.0315(3) 0.066(2) Uani 0.519(4) 1 d . . P A 2
C31A C -0.0235(4) 0.2632(11) 0.0340(4) 0.135(4) Uani 0.519(4) 1 d . . P A 2
H31C H -0.028194 0.154422 0.042347 0.162 Uiso 0.519(4) 1 calc R U P A 2
H31D H -0.048447 0.322998 0.061496 0.162 Uiso 0.519(4) 1 calc R U P A 2
C32A C -0.0462(7) 0.2972(13) -0.0202(4) 0.167(5) Uani 0.519(4) 1 d . . P A 2
H32D H -0.094517 0.271810 -0.023719 0.251 Uiso 0.519(4) 1 calc R U P A 2
H32E H -0.039714 0.405030 -0.027419 0.251 Uiso 0.519(4) 1 calc R U P A 2
H32F H -0.019664 0.238142 -0.046377 0.251 Uiso 0.519(4) 1 calc R U P A 2
C33A C 0.1002(4) 0.0832(7) 0.1523(2) 0.0713(19) Uani 0.519(4) 1 d . . P A 2
H33C H 0.148823 0.107967 0.146428 0.086 Uiso 0.519(4) 1 calc R U P A 2
H33D H 0.095315 -0.027414 0.148414 0.086 Uiso 0.519(4) 1 calc R U P A 2
C34A C 0.0820(4) 0.1249(8) 0.2089(2) 0.080(2) Uani 0.519(4) 1 d . . P A 2
H34D H 0.111559 0.070494 0.234308 0.120 Uiso 0.519(4) 1 calc R U P A 2
H34E H 0.088070 0.233805 0.213881 0.120 Uiso 0.519(4) 1 calc R U P A 2
H34F H 0.034411 0.098042 0.215872 0.120 Uiso 0.519(4) 1 calc R U P A 2
C35A C 0.1698(4) 0.1042(8) -0.0142(2) 0.074(2) Uani 0.519(4) 1 d . . P A 2
H35C H 0.193317 0.202284 -0.009721 0.089 Uiso 0.519(4) 1 calc R U P A 2
H35D H 0.144381 0.106666 -0.048895 0.089 Uiso 0.519(4) 1 calc R U P A 2
C36A C 0.2214(4) -0.0210(10) -0.0156(3) 0.097(2) Uani 0.519(4) 1 d . . P A 2
H36D H 0.252973 -0.004601 -0.045854 0.146 Uiso 0.519(4) 1 calc R U P A 2
H36E H 0.246905 -0.022371 0.018671 0.146 Uiso 0.519(4) 1 calc R U P A 2
H36F H 0.198069 -0.117794 -0.020423 0.146 Uiso 0.519(4) 1 calc R U P A 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.435(3) . ?
S11 O12 1.446(3) . ?
S11 N12 1.610(3) . ?
S11 C14 1.747(5) . ?
S12 C19 1.734(4) . ?
S12 C17 1.736(3) . ?
N11 C11 1.383(6) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.330(4) . ?
N13 C17 1.331(4) . ?
N13 C18 1.378(4) . ?
N13 H17 0.8800 . ?
C11 C12 1.388(7) . ?
C11 C16 1.410(7) . ?
C12 C13 1.372(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.404(6) . ?
C15 C16 1.376(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.329(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
P31 O32 1.436(8) . ?
P31 O34 1.505(8) . ?
P31 O33 1.562(8) . ?
P31 O31 1.632(8) . ?
O32 C31 1.452(9) . ?
O33 C33 1.552(8) . ?
O34 C35 1.503(8) . ?
C31 C32 1.437(10) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.485(7) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.504(8) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
P31A O31A 1.311(8) . ?
P31A O32A 1.496(8) . ?
P31A O33A 1.651(9) . ?
P31A O34A 1.701(8) . ?
O32A C31A 1.460(12) . ?
O33A C33A 1.395(9) . ?
O34A C35A 1.483(10) . ?
C31A C32A 1.437(10) . ?
C31A H31C 0.9900 . ?
C31A H31D 0.9900 . ?
C32A H32D 0.9800 . ?
C32A H32E 0.9800 . ?
C32A H32F 0.9800 . ?
C33A C34A 1.485(7) . ?
C33A H33C 0.9900 . ?
C33A H33D 0.9900 . ?
C34A H34D 0.9800 . ?
C34A H34E 0.9800 . ?
C34A H34F 0.9800 . ?
C35A C36A 1.504(8) . ?
C35A H35C 0.9900 . ?
C35A H35D 0.9900 . ?
C36A H36D 0.9800 . ?
C36A H36E 0.9800 . ?
C36A H36F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.71(18) . . ?
O11 S11 N12 104.69(16) . . ?
O12 S11 N12 110.48(16) . . ?
O11 S11 C14 107.06(18) . . ?
O12 S11 C14 108.11(19) . . ?
N12 S11 C14 107.2(2) . . ?
C19 S12 C17 90.42(17) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 122.2(2) . . ?
C17 N13 C18 115.0(3) . . ?
C17 N13 H17 122.5 . . ?
C18 N13 H17 122.5 . . ?
N11 C11 C12 121.7(5) . . ?
N11 C11 C16 119.6(5) . . ?
C12 C11 C16 118.7(4) . . ?
C13 C12 C11 120.9(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 118.7(4) . . ?
C13 C14 S11 120.4(3) . . ?
C15 C14 S11 120.9(3) . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.2(5) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N12 C17 N13 119.6(3) . . ?
N12 C17 S12 130.3(2) . . ?
N13 C17 S12 110.1(2) . . ?
C19 C18 N13 113.1(3) . . ?
C19 C18 H18 123.4 . . ?
N13 C18 H18 123.4 . . ?
C18 C19 S12 111.3(3) . . ?
C18 C19 H19 124.3 . . ?
S12 C19 H19 124.3 . . ?
O32 P31 O34 111.7(5) . . ?
O32 P31 O33 113.7(5) . . ?
O34 P31 O33 106.8(4) . . ?
O32 P31 O31 111.4(5) . . ?
O34 P31 O31 110.1(5) . . ?
O33 P31 O31 102.7(4) . . ?
C31 O32 P31 130.5(7) . . ?
C33 O33 P31 113.6(5) . . ?
C35 O34 P31 122.1(6) . . ?
O32 C31 C32 120.3(10) . . ?
O32 C31 H31A 107.2 . . ?
C32 C31 H31A 107.2 . . ?
O32 C31 H31B 107.2 . . ?
C32 C31 H31B 107.2 . . ?
H31A C31 H31B 106.9 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 O33 99.6(5) . . ?
C34 C33 H33A 111.9 . . ?
O33 C33 H33A 111.9 . . ?
C34 C33 H33B 111.9 . . ?
O33 C33 H33B 111.9 . . ?
H33A C33 H33B 109.6 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O34 C35 C36 107.2(6) . . ?
O34 C35 H35A 110.3 . . ?
C36 C35 H35A 110.3 . . ?
O34 C35 H35B 110.3 . . ?
C36 C35 H35B 110.3 . . ?
H35A C35 H35B 108.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O31A P31A O32A 123.3(5) . . ?
O31A P31A O33A 119.3(5) . . ?
O32A P31A O33A 102.0(5) . . ?
O31A P31A O34A 113.9(5) . . ?
O32A P31A O34A 102.1(5) . . ?
O33A P31A O34A 90.4(4) . . ?
C31A O32A P31A 125.0(7) . . ?
C33A O33A P31A 117.3(6) . . ?
C35A O34A P31A 111.3(6) . . ?
C32A C31A O32A 100.4(9) . . ?
C32A C31A H31C 111.7 . . ?
O32A C31A H31C 111.7 . . ?
C32A C31A H31D 111.7 . . ?
O32A C31A H31D 111.7 . . ?
H31C C31A H31D 109.5 . . ?
C31A C32A H32D 109.5 . . ?
C31A C32A H32E 109.5 . . ?
H32D C32A H32E 109.5 . . ?
C31A C32A H32F 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 109.5 . . ?
O33A C33A C34A 115.9(6) . . ?
O33A C33A H33C 108.3 . . ?
C34A C33A H33C 108.3 . . ?
O33A C33A H33D 108.3 . . ?
C34A C33A H33D 108.3 . . ?
H33C C33A H33D 107.4 . . ?
C33A C34A H34D 109.5 . . ?
C33A C34A H34E 109.5 . . ?
H34D C34A H34E 109.5 . . ?
C33A C34A H34F 109.5 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 109.5 . . ?
O34A C35A C36A 109.9(6) . . ?
O34A C35A H35C 109.7 . . ?
C36A C35A H35C 109.7 . . ?
O34A C35A H35D 109.7 . . ?
C36A C35A H35D 109.7 . . ?
H35C C35A H35D 108.2 . . ?
C35A C36A H36D 109.5 . . ?
C35A C36A H36E 109.5 . . ?
H36D C36A H36E 109.5 . . ?
C35A C36A H36F 109.5 . . ?
H36D C36A H36F 109.5 . . ?
H36E C36A H36F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 153.6(3) . . . . ?
O12 S11 N12 C17 24.7(4) . . . . ?
C14 S11 N12 C17 -92.9(4) . . . . ?
N11 C11 C12 C13 -179.9(5) . . . . ?
C16 C11 C12 C13 0.8(8) . . . . ?
C11 C12 C13 C14 -1.3(8) . . . . ?
C12 C13 C14 C15 1.2(7) . . . . ?
C12 C13 C14 S11 -179.0(4) . . . . ?
O11 S11 C14 C13 21.6(4) . . . . ?
O12 S11 C14 C13 150.5(3) . . . . ?
N12 S11 C14 C13 -90.3(4) . . . . ?
O11 S11 C14 C15 -158.6(3) . . . . ?
O12 S11 C14 C15 -29.6(4) . . . . ?
N12 S11 C14 C15 89.5(4) . . . . ?
C13 C14 C15 C16 -0.5(6) . . . . ?
S11 C14 C15 C16 179.6(3) . . . . ?
C14 C15 C16 C11 0.0(7) . . . . ?
N11 C11 C16 C15 -179.5(5) . . . . ?
C12 C11 C16 C15 -0.1(8) . . . . ?
S11 N12 C17 N13 179.2(3) . . . . ?
S11 N12 C17 S12 0.1(6) . . . . ?
C18 N13 C17 N12 -178.7(4) . . . . ?
C18 N13 C17 S12 0.7(5) . . . . ?
C19 S12 C17 N12 177.9(4) . . . . ?
C19 S12 C17 N13 -1.3(4) . . . . ?
C17 N13 C18 C19 0.7(6) . . . . ?
N13 C18 C19 S12 -1.7(5) . . . . ?
C17 S12 C19 C18 1.7(4) . . . . ?
O34 P31 O32 C31 -154.5(9) . . . . ?
O33 P31 O32 C31 84.6(10) . . . . ?
O31 P31 O32 C31 -30.9(11) . . . . ?
O32 P31 O33 C33 59.7(7) . . . . ?
O34 P31 O33 C33 -63.9(7) . . . . ?
O31 P31 O33 C33 -179.8(6) . . . . ?
O32 P31 O34 C35 41.2(9) . . . . ?
O33 P31 O34 C35 166.1(7) . . . . ?
O31 P31 O34 C35 -83.1(8) . . . . ?
P31 O32 C31 C32 108.1(12) . . . . ?
P31 O33 C33 C34 -161.4(6) . . . . ?
P31 O34 C35 C36 -161.1(7) . . . . ?
O31A P31A O32A C31A -150.0(10) . . . . ?
O33A P31A O32A C31A -12.5(12) . . . . ?
O34A P31A O32A C31A 80.4(11) . . . . ?
O31A P31A O33A C33A -37.7(10) . . . . ?
O32A P31A O33A C33A -177.3(8) . . . . ?
O34A P31A O33A C33A 80.3(8) . . . . ?
O31A P31A O34A C35A -50.2(7) . . . . ?
O32A P31A O34A C35A 85.0(7) . . . . ?
O33A P31A O34A C35A -172.7(7) . . . . ?
P31A O32A C31A C32A -153.4(10) . . . . ?
P31A O33A C33A C34A 125.1(7) . . . . ?
P31A O34A C35A C36A 138.6(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O31^a 0.88 2.12 2.998(9) 174.9 . yes
N11 H10 O31A^b 0.88 2.36 3.104(9) 142.4 . yes
N11 H11 O34^a 0.88 2.31 3.065(10) 143.7 4 yes
N11 H11 O31A^b 0.88 2.38 3.232(9) 163.9 4 yes
N13 H17 N12 0.88 1.95 2.817(4) 168.9 2_575 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_30
_database_code_depnum_ccdc_archive 'CCDC 2120791'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 3n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1,12-dodecanedinitrile (2:1) solvate'
_chemical_name_common            'Sulfathiazole, dodecanedinitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C12 H20 N2'
_chemical_formula_sum            'C30 H38 N8 O4 S4'
_chemical_formula_weight         702.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6785(2)
_cell_length_b                   19.9110(6)
_cell_length_c                   10.0217(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.776(1)
_cell_angle_gamma                90
_cell_volume                     1715.80(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8830
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12957
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.563
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3882
_reflns_number_gt                3035
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  3n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.10      60     69     87.0     3.28     454.5   30.32  0.0700  0.0252
3.10 - 2.10     144    144    100.0     4.24     242.1   32.18  0.0513  0.0251
2.10 - 1.67     198    198    100.0     4.31     149.0   31.95  0.0697  0.0250
1.67 - 1.46     198    198    100.0     4.36     111.4   28.68  0.0620  0.0278
1.46 - 1.33     202    202    100.0     4.26     101.3   23.13  0.0556  0.0324
1.33 - 1.23     205    205    100.0     4.30      81.6   17.89  0.0547  0.0367
1.23 - 1.16     198    198    100.0     4.26      94.8   19.82  0.0593  0.0380
1.16 - 1.10     196    196    100.0     4.33      71.9   17.24  0.0756  0.0426
1.10 - 1.05     216    216    100.0     4.19      47.1   13.04  0.0726  0.0502
1.05 - 1.01     192    192    100.0     4.20      50.5   14.02  0.0701  0.0527
1.01 - 0.97     235    235    100.0     3.92      37.8   11.21  0.0766  0.0625
0.97 - 0.94     194    194    100.0     3.35      30.2    9.43  0.0792  0.0807
0.94 - 0.91     226    228     99.1     3.20      30.2    8.45  0.0828  0.0831
0.91 - 0.89     174    174    100.0     2.83      27.1    7.37  0.0878  0.0991
0.89 - 0.87     176    176    100.0     2.56      21.9    5.81  0.1200  0.1215
0.87 - 0.85     206    207     99.5     2.24      23.9    5.73  0.1079  0.1296
0.85 - 0.83     207    211     98.1     2.10      20.4    5.07  0.1231  0.1483
0.83 - 0.81     256    261     98.1     1.85      18.1    4.24  0.1145  0.1833
0.81 - 0.80     124    128     96.9     1.79      20.1    4.15  0.1022  0.1816
0.80 - 0.78     260    267     97.4     1.69      19.7    3.78  0.1003  0.1954
0.78 - 0.77     140    160     87.5     1.38      16.6    3.29  0.1228  0.2389
#------------------------------------------------------------------------------
0.87 - 0.77    1193   1234     96.7     1.86      19.9    4.42  0.1116  0.1738
 Inf - 0.77    4007   4059     98.7     3.26      64.3   13.37  0.0669  0.0512
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+0.2648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3882
_refine_ls_number_parameters     221
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.064

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.52263(5) 0.15342(2) 0.41106(4) 0.02137(13) Uani 1 1 d . . . . .
S12 S 0.67749(5) 0.14195(2) 0.73267(5) 0.02678(14) Uani 1 1 d . . . . .
O11 O 0.50005(14) 0.13263(6) 0.27174(12) 0.0276(3) Uani 1 1 d . . . . .
O12 O 0.65141(13) 0.19788(6) 0.45492(13) 0.0297(3) Uani 1 1 d . . . . .
N11 N -0.05957(17) 0.27514(9) 0.54094(17) 0.0320(4) Uani 1 1 d D . . . .
H10 H -0.061(2) 0.3018(10) 0.6099(18) 0.039(6) Uiso 1 1 d D . . . .
H11 H -0.1460(19) 0.2526(9) 0.5178(19) 0.045(6) Uiso 1 1 d D . . . .
N12 N 0.53710(15) 0.08363(7) 0.49246(13) 0.0211(3) Uani 1 1 d . . . . .
N13 N 0.59668(16) 0.02120(7) 0.68645(14) 0.0222(3) Uani 1 1 d . . . . .
H17 H 0.556(2) -0.0122(11) 0.647(2) 0.041(6) Uiso 1 1 d . . . . .
C11 C 0.07542(18) 0.24750(9) 0.51070(17) 0.0223(4) Uani 1 1 d . . . . .
C12 C 0.07306(19) 0.19751(9) 0.41166(17) 0.0234(4) Uani 1 1 d . . . . .
H12 H -0.023813 0.182230 0.366313 0.028 Uiso 1 1 calc R U . . .
C13 C 0.20927(19) 0.17028(8) 0.37925(16) 0.0228(4) Uani 1 1 d . . . . .
H13 H 0.206016 0.136659 0.311655 0.027 Uiso 1 1 calc R U . . .
C14 C 0.35192(18) 0.19223(8) 0.44602(16) 0.0198(3) Uani 1 1 d . . . . .
C15 C 0.35675(18) 0.24182(8) 0.54452(16) 0.0208(4) Uani 1 1 d . . . . .
H15 H 0.454001 0.256625 0.589933 0.025 Uiso 1 1 calc R U . . .
C16 C 0.22048(18) 0.26948(8) 0.57628(16) 0.0217(4) Uani 1 1 d . . . . .
H16 H 0.224542 0.303608 0.642906 0.026 Uiso 1 1 calc R U . . .
C17 C 0.59580(17) 0.08007(8) 0.62178(16) 0.0201(3) Uani 1 1 d . . . . .
C18 C 0.6581(2) 0.02253(9) 0.82120(17) 0.0277(4) Uani 1 1 d . . . . .
H18 H 0.665308 -0.015845 0.878044 0.033 Uiso 1 1 calc R U . . .
C19 C 0.7058(2) 0.08351(9) 0.86233(18) 0.0296(4) Uani 1 1 d . . . . .
H19 H 0.750077 0.093849 0.951899 0.036 Uiso 1 1 calc R U . . .
N31 N 0.07799(18) 0.11569(9) 1.06221(17) 0.0376(4) Uani 1 1 d . . . . .
C31 C 0.1055(2) 0.12767(9) 0.95650(19) 0.0273(4) Uani 1 1 d . . . . .
C32 C 0.1433(2) 0.14031(9) 0.82105(18) 0.0293(4) Uani 1 1 d . . . . .
H32A H 0.187211 0.186047 0.817016 0.035 Uiso 1 1 calc R U . . .
H32B H 0.047230 0.138020 0.755602 0.035 Uiso 1 1 calc R U . . .
C33 C 0.2608(2) 0.08887(9) 0.78261(19) 0.0307(4) Uani 1 1 d . . . . .
H33A H 0.282090 0.098488 0.689927 0.037 Uiso 1 1 calc R U . . .
H33B H 0.359579 0.094264 0.843750 0.037 Uiso 1 1 calc R U . . .
C34 C 0.2065(2) 0.01614(9) 0.78926(19) 0.0314(4) Uani 1 1 d . . . . .
H34A H 0.188808 0.006182 0.882774 0.038 Uiso 1 1 calc R U . . .
H34B H 0.290765 -0.013769 0.767486 0.038 Uiso 1 1 calc R U . . .
C35 C 0.0581(2) -0.00033(9) 0.69453(17) 0.0298(4) Uani 1 1 d . . . . .
H35A H 0.027969 -0.047320 0.710354 0.036 Uiso 1 1 calc R U . . .
H35B H -0.026652 0.029142 0.716830 0.036 Uiso 1 1 calc R U . . .
C36 C 0.0736(2) 0.00811(10) 0.54694(18) 0.0304(4) Uani 1 1 d . . . . .
H36A H 0.158257 -0.021435 0.524591 0.037 Uiso 1 1 calc R U . . .
H36B H 0.103966 0.055071 0.531141 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.4441(12) . ?
S11 O12 1.4467(12) . ?
S11 N12 1.6077(14) . ?
S11 C14 1.7479(16) . ?
S12 C19 1.7368(19) . ?
S12 C17 1.7443(16) . ?
N11 C11 1.365(2) . ?
N11 H10 0.872(15) . ?
N11 H11 0.878(15) . ?
N12 C17 1.329(2) . ?
N13 C17 1.339(2) . ?
N13 C18 1.383(2) . ?
N13 H17 0.83(2) . ?
C11 C12 1.404(2) . ?
C11 C16 1.409(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.330(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C31 1.142(2) . ?
C31 C32 1.461(3) . ?
C32 C33 1.530(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.527(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.528(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.513(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C36 1.516(3) 3_556 ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.86(7) . . ?
O11 S11 N12 103.53(7) . . ?
O12 S11 N12 111.76(7) . . ?
O11 S11 C14 108.22(7) . . ?
O12 S11 C14 108.03(8) . . ?
N12 S11 C14 106.89(8) . . ?
C19 S12 C17 90.43(8) . . ?
C11 N11 H10 121.8(12) . . ?
C11 N11 H11 117.6(13) . . ?
H10 N11 H11 114.6(14) . . ?
C17 N12 S11 122.30(11) . . ?
C17 N13 C18 115.60(15) . . ?
C17 N13 H17 119.6(15) . . ?
C18 N13 H17 124.6(15) . . ?
N11 C11 C12 120.79(15) . . ?
N11 C11 C16 120.72(16) . . ?
C12 C11 C16 118.48(15) . . ?
C13 C12 C11 120.96(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.81(16) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.10(15) . . ?
C15 C14 S11 120.69(12) . . ?
C13 C14 S11 119.10(13) . . ?
C16 C15 C14 120.12(15) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 120.53(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N12 C17 N13 119.68(14) . . ?
N12 C17 S12 130.76(13) . . ?
N13 C17 S12 109.56(12) . . ?
C19 C18 N13 112.50(17) . . ?
C19 C18 H18 123.8 . . ?
N13 C18 H18 123.8 . . ?
C18 C19 S12 111.91(13) . . ?
C18 C19 H19 124.0 . . ?
S12 C19 H19 124.0 . . ?
N31 C31 C32 177.7(2) . . ?
C31 C32 C33 111.08(15) . . ?
C31 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
C31 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C34 C33 C32 113.82(15) . . ?
C34 C33 H33A 108.8 . . ?
C32 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C32 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 C35 114.53(15) . . ?
C33 C34 H34A 108.6 . . ?
C35 C34 H34A 108.6 . . ?
C33 C34 H34B 108.6 . . ?
C35 C34 H34B 108.6 . . ?
H34A C34 H34B 107.6 . . ?
C36 C35 C34 113.86(15) . . ?
C36 C35 H35A 108.8 . . ?
C34 C35 H35A 108.8 . . ?
C36 C35 H35B 108.8 . . ?
C34 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C35 C36 C36 113.84(18) . 3_556 ?
C35 C36 H36A 108.8 . . ?
C36 C36 H36A 108.8 3_556 . ?
C35 C36 H36B 108.8 . . ?
C36 C36 H36B 108.8 3_556 . ?
H36A C36 H36B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 163.21(13) . . . . ?
O12 S11 N12 C17 35.36(15) . . . . ?
C14 S11 N12 C17 -82.64(14) . . . . ?
N11 C11 C12 C13 178.91(16) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C12 C13 C14 S11 176.02(13) . . . . ?
O11 S11 C14 C15 -151.24(13) . . . . ?
O12 S11 C14 C15 -22.59(16) . . . . ?
N12 S11 C14 C15 97.82(14) . . . . ?
O11 S11 C14 C13 32.36(15) . . . . ?
O12 S11 C14 C13 161.01(13) . . . . ?
N12 S11 C14 C13 -78.58(14) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
S11 C14 C15 C16 -176.47(12) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
N11 C11 C16 C15 -179.41(16) . . . . ?
C12 C11 C16 C15 -0.7(2) . . . . ?
S11 N12 C17 N13 176.12(12) . . . . ?
S11 N12 C17 S12 -3.5(2) . . . . ?
C18 N13 C17 N12 -179.13(14) . . . . ?
C18 N13 C17 S12 0.57(18) . . . . ?
C19 S12 C17 N12 178.90(17) . . . . ?
C19 S12 C17 N13 -0.76(13) . . . . ?
C17 N13 C18 C19 0.0(2) . . . . ?
N13 C18 C19 S12 -0.6(2) . . . . ?
C17 S12 C19 C18 0.80(15) . . . . ?
C31 C32 C33 C34 57.5(2) . . . . ?
C32 C33 C34 C35 61.2(2) . . . . ?
C33 C34 C35 C36 62.5(2) . . . . ?
C34 C35 C36 C36 -179.9(2) . . . 3_556 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.872(15) 2.094(16) 2.944(2) 164.3(16) 4_566 yes
N11 H11 O12 0.878(15) 2.092(16) 2.9691(19) 177.6(18) 1_455 yes
N13 H17 O11 0.83(2) 2.60(2) 3.2182(19) 132.3(19) 3_656 yes
N13 H17 N12 0.83(2) 2.08(2) 2.891(2) 167(2) 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_13
_database_code_depnum_ccdc_archive 'CCDC 2120787'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 14o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_13                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.00 angstrom. Data were integrated to 0.84
angstrom resolution, but this gives well below 50% observed at the 2sigma(I)
level. For the refinement, the data are truncated at 0.95 angstrom resolution.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 4-methyl 1,3-dioxalene-2-one (1:1) solvate'
_chemical_name_common            'Sulfathiazole, propylene carbonate solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H6 O3'
_chemical_formula_sum            'C13 H15 N3 O5 S2'
_chemical_formula_weight         357.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.628(2)
_cell_length_b                   21.151(4)
_cell_length_c                   9.135(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.70(3)
_cell_angle_gamma                90
_cell_volume                     1652.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5401
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      21.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.350
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_reflns_number            5401
_diffrn_reflns_av_unetI/netI     0.1464
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         21.964
_diffrn_reflns_theta_full        21.964
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             1929
_reflns_number_gt                1140
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  14o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.79      38     41     92.7     3.37     154.0   66.52  0.1848  0.0112
3.79 - 2.46      87     91     95.6     3.08      60.9   28.38  0.1631  0.0238
2.46 - 1.93     124    129     96.1     2.99      30.7   17.42  0.1295  0.0404
1.93 - 1.68     125    127     98.4     3.06      19.2   12.02  0.0629  0.0618
1.68 - 1.52     131    134     97.8     3.01      13.2    8.82  0.0547  0.0851
1.52 - 1.41     127    135     94.1     2.96      11.9    7.80  0.0504  0.1028
1.41 - 1.33     119    121     98.3     3.02       8.1    5.90  0.0634  0.1312
1.33 - 1.26     131    135     97.0     2.90       6.2    4.55  0.0633  0.1725
1.26 - 1.20     134    137     97.8     2.87       7.4    5.08  0.0627  0.1653
1.20 - 1.16     110    114     96.5     2.74       6.6    4.08  0.0614  0.1849
1.16 - 1.12     127    129     98.4     2.67       4.6    3.23  0.1009  0.2802
1.12 - 1.08     127    136     93.4     2.50       4.9    3.21  0.0883  0.2711
1.08 - 1.05     117    126     92.9     2.17       3.3    2.20  0.1035  0.3926
1.05 - 1.02     123    138     89.1     2.14       3.0    2.14  0.1338  0.4489
1.02 - 0.99     144    167     86.2     1.83       2.1    1.48  0.1565  0.6432
0.99 - 0.96     144    160     90.0     1.92       1.6    1.24  0.1804  0.8058
0.96 - 0.94     127    150     84.7     1.73       1.7    1.20  0.1588  0.7640
0.94 - 0.92     124    137     90.5     1.83       1.3    0.99  0.1970  0.9773
0.92 - 0.90     120    151     79.5     1.40       1.3    0.92  0.2254  1.0575
0.90 - 0.88     103    172     59.9     0.93       1.2    0.83  0.1792  1.1559
0.88 - 0.84     114    380     30.0     0.40       1.0    0.63  0.2037  1.4592
#--------------------------------------------------------------------------------
0.94 - 0.84     461    840     54.9     0.92       1.2    0.85  0.2039  1.1366
 Inf - 0.84    2496   3010     82.9     2.11      11.0    6.21  0.1227  0.1164
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The H atoms of the NH2 group could not readily be refined, so they were
placed in-plane and allowed to ride. This is an approximation.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0264P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1929
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_restrained_S_all      0.802
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.053

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.53297(14) 0.14609(5) 0.39717(13) 0.0565(4) Uani 1 1 d . . . . .
S12 S 0.63363(17) 0.13693(5) 0.75720(14) 0.0804(5) Uani 1 1 d . . . . .
O11 O 0.5158(4) 0.12740(11) 0.2439(3) 0.0705(9) Uani 1 1 d . . . . .
O12 O 0.6636(3) 0.18596(12) 0.4506(3) 0.0726(9) Uani 1 1 d . . . . .
N11 N -0.0489(5) 0.26403(17) 0.5309(4) 0.0860(13) Uani 1 1 d . . . . .
H10 H -0.046799 0.294889 0.595714 0.129 Uiso 1 1 calc R U . . .
H11 H -0.139088 0.249268 0.488011 0.129 Uiso 1 1 calc R U . . .
N12 N 0.5385(4) 0.08036(13) 0.4850(4) 0.0524(9) Uani 1 1 d . . . . .
N13 N 0.5699(4) 0.02299(14) 0.7012(4) 0.0596(10) Uani 1 1 d . . . . .
H17 H 0.542178 -0.012519 0.654736 0.089 Uiso 1 1 calc R U . . .
C11 C 0.0873(6) 0.23913(18) 0.4968(5) 0.0536(12) Uani 1 1 d . . . . .
C12 C 0.0832(6) 0.18904(19) 0.3968(4) 0.0584(13) Uani 1 1 d . . . . .
H12 H -0.014639 0.173416 0.351058 0.070 Uiso 1 1 calc R U . . .
C13 C 0.2183(6) 0.16231(17) 0.3643(5) 0.0557(12) Uani 1 1 d . . . . .
H13 H 0.213999 0.128520 0.295309 0.067 Uiso 1 1 calc R U . . .
C14 C 0.3633(5) 0.18445(17) 0.4320(4) 0.0484(11) Uani 1 1 d . . . . .
C15 C 0.3662(5) 0.23465(17) 0.5297(4) 0.0545(12) Uani 1 1 d . . . . .
H15 H 0.463876 0.250732 0.574781 0.065 Uiso 1 1 calc R U . . .
C16 C 0.2311(6) 0.26136(17) 0.5624(4) 0.0563(12) Uani 1 1 d . . . . .
H16 H 0.235637 0.295452 0.630510 0.068 Uiso 1 1 calc R U . . .
C17 C 0.5753(5) 0.07787(17) 0.6297(5) 0.0511(11) Uani 1 1 d . . . . .
C18 C 0.6105(6) 0.0254(2) 0.8520(5) 0.0791(15) Uani 1 1 d . . . . .
H18 H 0.611908 -0.010538 0.914594 0.095 Uiso 1 1 calc R U . . .
C19 C 0.6474(6) 0.0832(2) 0.9006(5) 0.0911(17) Uani 1 1 d . . . . .
H19 H 0.677657 0.093672 1.001486 0.109 Uiso 1 1 calc R U . . .
O30 O 0.1892(6) 0.0213(2) 0.8197(6) 0.166(2) Uani 1 1 d . . . . .
O31 O -0.0286(6) 0.0113(3) 0.6829(6) 0.165(2) Uani 1 1 d . . . . .
O32 O 0.0640(7) -0.0693(2) 0.8201(6) 0.180(3) Uani 1 1 d . . . . .
C30 C 0.0751(11) -0.0164(4) 0.7786(9) 0.133(3) Uani 1 1 d . . . . .
C31 C 0.0279(13) 0.0726(4) 0.6514(11) 0.182(4) Uani 1 1 d . . . . .
H31A H -0.053865 0.104849 0.658869 0.219 Uiso 1 1 calc R U . . .
H31B H 0.056607 0.073752 0.550069 0.219 Uiso 1 1 calc R U . . .
C32 C 0.1630(10) 0.0851(4) 0.7580(10) 0.141(3) Uani 1 1 d . . . . .
H32 H 0.253125 0.097831 0.706132 0.169 Uiso 1 1 calc R U . . .
C33 C 0.1436(11) 0.1305(3) 0.8736(9) 0.192(4) Uani 1 1 d . . . . .
H33A H 0.134660 0.173162 0.831450 0.288 Uiso 1 1 calc R U . . .
H33B H 0.234380 0.128540 0.950390 0.288 Uiso 1 1 calc R U . . .
H33C H 0.048605 0.120398 0.916879 0.288 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.439(3) . ?
S11 O11 1.444(3) . ?
S11 N12 1.603(3) . ?
S11 C14 1.740(4) . ?
S12 C19 1.727(5) . ?
S12 C17 1.736(4) . ?
N11 C11 1.362(5) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.318(5) . ?
N13 C17 1.336(4) . ?
N13 C18 1.376(5) . ?
N13 H17 0.8800 . ?
C11 C16 1.386(5) . ?
C11 C12 1.396(5) . ?
C12 C13 1.364(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(5) . ?
C15 C16 1.363(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.324(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C30 1.284(7) . ?
O30 C32 1.468(7) . ?
O31 C30 1.304(7) . ?
O31 C31 1.427(8) . ?
O32 C30 1.188(7) . ?
C31 C32 1.440(9) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.453(9) . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 117.61(18) . . ?
O12 S11 N12 111.67(17) . . ?
O11 S11 N12 103.90(16) . . ?
O12 S11 C14 107.73(19) . . ?
O11 S11 C14 108.99(19) . . ?
N12 S11 C14 106.40(18) . . ?
C19 S12 C17 91.1(2) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 121.6(3) . . ?
C17 N13 C18 115.9(3) . . ?
C17 N13 H17 122.0 . . ?
C18 N13 H17 122.0 . . ?
N11 C11 C16 121.4(4) . . ?
N11 C11 C12 119.7(4) . . ?
C16 C11 C12 118.9(4) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 118.6(4) . . ?
C15 C14 S11 122.2(3) . . ?
C13 C14 S11 119.2(3) . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N12 C17 N13 120.4(3) . . ?
N12 C17 S12 130.8(3) . . ?
N13 C17 S12 108.8(3) . . ?
C19 C18 N13 112.8(4) . . ?
C19 C18 H18 123.6 . . ?
N13 C18 H18 123.6 . . ?
C18 C19 S12 111.4(4) . . ?
C18 C19 H19 124.3 . . ?
S12 C19 H19 124.3 . . ?
C30 O30 C32 112.8(6) . . ?
C30 O31 C31 108.8(7) . . ?
O32 C30 O30 125.7(8) . . ?
O32 C30 O31 124.1(8) . . ?
O30 C30 O31 110.2(7) . . ?
O31 C31 C32 107.3(7) . . ?
O31 C31 H31A 110.2 . . ?
C32 C31 H31A 110.2 . . ?
O31 C31 H31B 110.2 . . ?
C32 C31 H31B 110.2 . . ?
H31A C31 H31B 108.5 . . ?
C31 C32 C33 116.8(8) . . ?
C31 C32 O30 99.2(6) . . ?
C33 C32 O30 110.8(7) . . ?
C31 C32 H32 109.8 . . ?
C33 C32 H32 109.8 . . ?
O30 C32 H32 109.8 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 42.7(4) . . . . ?
O11 S11 N12 C17 170.4(3) . . . . ?
C14 S11 N12 C17 -74.6(4) . . . . ?
N11 C11 C12 C13 -178.2(4) . . . . ?
C16 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 0.6(6) . . . . ?
C12 C13 C14 C15 -1.3(6) . . . . ?
C12 C13 C14 S11 175.9(3) . . . . ?
O12 S11 C14 C15 -16.0(4) . . . . ?
O11 S11 C14 C15 -144.6(3) . . . . ?
N12 S11 C14 C15 103.9(3) . . . . ?
O12 S11 C14 C13 166.9(3) . . . . ?
O11 S11 C14 C13 38.2(3) . . . . ?
N12 S11 C14 C13 -73.2(3) . . . . ?
C13 C14 C15 C16 1.4(6) . . . . ?
S11 C14 C15 C16 -175.8(3) . . . . ?
C14 C15 C16 C11 -0.7(6) . . . . ?
N11 C11 C16 C15 178.2(4) . . . . ?
C12 C11 C16 C15 -0.1(6) . . . . ?
S11 N12 C17 N13 176.0(3) . . . . ?
S11 N12 C17 S12 -3.7(6) . . . . ?
C18 N13 C17 N12 180.0(4) . . . . ?
C18 N13 C17 S12 -0.3(5) . . . . ?
C19 S12 C17 N12 179.7(4) . . . . ?
C19 S12 C17 N13 0.1(3) . . . . ?
C17 N13 C18 C19 0.5(6) . . . . ?
N13 C18 C19 S12 -0.4(6) . . . . ?
C17 S12 C19 C18 0.2(4) . . . . ?
C32 O30 C30 O32 -175.3(9) . . . . ?
C32 O30 C30 O31 5.0(10) . . . . ?
C31 O31 C30 O32 -175.9(9) . . . . ?
C31 O31 C30 O30 3.8(10) . . . . ?
C30 O31 C31 C32 -11.0(11) . . . . ?
O31 C31 C32 C33 -106.6(8) . . . . ?
O31 C31 C32 O30 12.4(10) . . . . ?
C30 O30 C32 C31 -11.1(10) . . . . ?
C30 O30 C32 C33 112.3(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 S11 0.88 3.02 3.831(4) 154.5 4_566 yes
N11 H10 O11 0.88 2.15 3.013(4) 166.1 4_566 yes
N11 H11 O12 0.88 2.16 2.989(5) 157.3 1_455 yes
N13 H17 S11 0.88 2.92 3.765(3) 160.6 3_656 yes
N13 H17 N12 0.88 1.98 2.850(4) 167.7 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_34
_database_code_depnum_ccdc_archive 'CCDC 2120795'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 7n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, morpholine-4-carbonitrile (1:1) solvate'
_chemical_name_common            
'Sulfathiazole, morpholine-4-carbonitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C5 H8 N2 O'
_chemical_formula_sum            'C14 H17 N5 O3 S2'
_chemical_formula_weight         367.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3551(9)
_cell_length_b                   18.880(3)
_cell_length_c                   10.7764(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.790(9)
_cell_angle_gamma                90
_cell_volume                     1688.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    15509
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.339
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15509
_diffrn_reflns_av_unetI/netI     0.1850
_diffrn_reflns_av_R_equivalents  0.1556
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.634
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3826
_reflns_number_gt                1704
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  7n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.53      47     48     97.9     4.90     862.9   29.85  0.0670  0.0271
3.53 - 2.34     108    108    100.0     5.63     470.9   23.60  0.0528  0.0303
2.34 - 1.85     152    152    100.0     5.71     264.5   18.76  0.0706  0.0362
1.85 - 1.60     156    156    100.0     5.75     179.7   14.87  0.0917  0.0460
1.60 - 1.45     156    156    100.0     5.75     128.6   12.50  0.1073  0.0567
1.45 - 1.34     159    159    100.0     5.67     115.9    9.77  0.1163  0.0666
1.34 - 1.26     164    164    100.0     5.71      83.0    8.68  0.1520  0.0887
1.26 - 1.19     153    153    100.0     5.54      96.8    8.74  0.1526  0.0875
1.19 - 1.14     164    164    100.0     5.43      84.9    6.82  0.1609  0.1034
1.14 - 1.10     132    132    100.0     5.36      72.1    6.22  0.1925  0.1219
1.10 - 1.06     166    166    100.0     4.90      67.0    5.87  0.1975  0.1411
1.06 - 1.03     136    136    100.0     4.54      43.6    3.81  0.2831  0.2197
1.03 - 1.00     160    160    100.0     4.48      43.1    3.76  0.2820  0.2289
1.00 - 0.97     172    173     99.4     4.19      28.9    2.43  0.3964  0.3592
0.97 - 0.94     185    188     98.4     3.87      27.6    2.39  0.4254  0.4084
0.94 - 0.92     143    145     98.6     3.67      28.1    2.14  0.4333  0.4292
0.92 - 0.90     153    153    100.0     3.37      29.0    2.03  0.4360  0.4500
0.90 - 0.88     189    190     99.5     2.90      21.0    1.34  0.5244  0.7366
0.88 - 0.87      90     91     98.9     2.76      21.3    1.26  0.5050  0.7663
0.87 - 0.85     186    186    100.0     2.64      22.5    1.26  0.5059  0.7714
0.85 - 0.84     105    106     99.1     2.39      20.2    1.06  0.4898  0.9436
#------------------------------------------------------------------------------
0.94 - 0.84     866    871     99.4     2.98      23.8    1.53  0.4747  0.6461
 Inf - 0.84    3076   3086     99.7     4.53      99.1    7.03  0.1309  0.1133
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3826
_refine_ls_number_parameters     226
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1879
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.070

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.50251(10) 0.15996(5) 0.37283(9) 0.0330(3) Uani 1 1 d . . . . .
S12 S 0.70465(11) 0.16141(6) 0.65893(10) 0.0420(3) Uani 1 1 d . . . . .
O11 O 0.4708(3) 0.13170(14) 0.2486(2) 0.0380(7) Uani 1 1 d . . . . .
O12 O 0.6373(3) 0.20802(14) 0.3989(2) 0.0408(7) Uani 1 1 d . . . . .
N11 N -0.0880(4) 0.3014(2) 0.4976(4) 0.0396(9) Uani 1 1 d D . . . .
H10 H -0.085(3) 0.3155(19) 0.571(3) 0.033(13) Uiso 1 1 d D . . . .
H11 H -0.174(4) 0.281(2) 0.473(3) 0.056(14) Uiso 1 1 d D . . . .
N12 N 0.5222(3) 0.09175(16) 0.4621(3) 0.0313(8) Uani 1 1 d . . . . .
N13 N 0.6102(3) 0.03449(17) 0.6473(3) 0.0346(8) Uani 1 1 d . . . . .
H17 H 0.564629 -0.005647 0.621014 0.052 Uiso 1 1 calc R U . . .
C11 C 0.0479(4) 0.2673(2) 0.4705(4) 0.0327(9) Uani 1 1 d . . . . .
C12 C 0.0426(4) 0.2211(2) 0.3700(3) 0.0319(9) Uani 1 1 d . . . . .
H12 H -0.058065 0.211110 0.322560 0.038 Uiso 1 1 calc R U . . .
C13 C 0.1806(4) 0.1894(2) 0.3377(4) 0.0325(9) Uani 1 1 d . . . . .
H13 H 0.174860 0.157588 0.268936 0.039 Uiso 1 1 calc R U . . .
C14 C 0.3293(4) 0.20446(19) 0.4072(3) 0.0283(9) Uani 1 1 d . . . . .
C15 C 0.3365(4) 0.25075(19) 0.5077(3) 0.0315(9) Uani 1 1 d . . . . .
H15 H 0.437216 0.261325 0.554471 0.038 Uiso 1 1 calc R U . . .
C16 C 0.1977(4) 0.28129(19) 0.5395(3) 0.0323(9) Uani 1 1 d . . . . .
H16 H 0.203238 0.312340 0.609197 0.039 Uiso 1 1 calc R U . . .
C17 C 0.6019(4) 0.0926(2) 0.5761(4) 0.0327(9) Uani 1 1 d . . . . .
C18 C 0.6946(4) 0.0413(2) 0.7644(4) 0.0405(10) Uani 1 1 d . . . . .
H18 H 0.710966 0.003576 0.822936 0.049 Uiso 1 1 calc R U . . .
C19 C 0.7503(5) 0.1063(2) 0.7864(4) 0.0423(11) Uani 1 1 d . . . . .
H19 H 0.808458 0.121026 0.863155 0.051 Uiso 1 1 calc R U . . .
O31 O 0.1961(3) 0.01286(15) 0.5929(3) 0.0461(7) Uani 1 1 d . . . . .
N31 N 0.1552(4) 0.05691(18) 0.8340(3) 0.0421(9) Uani 1 1 d . . . . .
N32 N 0.0994(4) 0.0942(2) 1.0441(3) 0.0490(10) Uani 1 1 d . . . . .
C31 C 0.1376(5) 0.0820(2) 0.6146(4) 0.0486(11) Uani 1 1 d . . . . .
H31A H 0.018300 0.081086 0.604661 0.058 Uiso 1 1 calc R U . . .
H31B H 0.172029 0.114832 0.551246 0.058 Uiso 1 1 calc R U . . .
C32 C 0.1977(5) 0.1090(2) 0.7427(4) 0.0449(11) Uani 1 1 d . . . . .
H32A H 0.316077 0.115423 0.750639 0.054 Uiso 1 1 calc R U . . .
H32B H 0.147399 0.155229 0.757290 0.054 Uiso 1 1 calc R U . . .
C33 C 0.2037(5) -0.0165(2) 0.8110(4) 0.0475(11) Uani 1 1 d . . . . .
H33A H 0.158026 -0.049032 0.869682 0.057 Uiso 1 1 calc R U . . .
H33B H 0.322608 -0.020639 0.824169 0.057 Uiso 1 1 calc R U . . .
C34 C 0.1422(5) -0.0355(2) 0.6790(4) 0.0501(12) Uani 1 1 d . . . . .
H34A H 0.179561 -0.083761 0.660635 0.060 Uiso 1 1 calc R U . . .
H34B H 0.022923 -0.035969 0.669298 0.060 Uiso 1 1 calc R U . . .
C35 C 0.1300(4) 0.0769(2) 0.9476(4) 0.0374(10) Uani 1 1 d . . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.436(3) . ?
S11 O12 1.448(3) . ?
S11 N12 1.604(3) . ?
S11 C14 1.751(3) . ?
S12 C19 1.729(4) . ?
S12 C17 1.744(4) . ?
N11 C11 1.366(5) . ?
N11 H10 0.83(2) . ?
N11 H11 0.83(3) . ?
N12 C17 1.327(4) . ?
N13 C17 1.335(5) . ?
N13 C18 1.377(5) . ?
N13 H17 0.8800 . ?
C11 C12 1.386(5) . ?
C11 C16 1.403(5) . ?
C12 C13 1.380(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.403(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C15 C16 1.374(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.325(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O31 C34 1.414(5) . ?
O31 C31 1.422(5) . ?
N31 C35 1.322(6) . ?
N31 C32 1.464(5) . ?
N31 C33 1.473(5) . ?
N32 C35 1.147(5) . ?
C31 C32 1.501(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.498(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.87(15) . . ?
O11 S11 N12 104.78(16) . . ?
O12 S11 N12 111.37(16) . . ?
O11 S11 C14 108.04(16) . . ?
O12 S11 C14 107.56(16) . . ?
N12 S11 C14 106.68(16) . . ?
C19 S12 C17 90.4(2) . . ?
C11 N11 H10 115(2) . . ?
C11 N11 H11 115(3) . . ?
H10 N11 H11 112.2(18) . . ?
C17 N12 S11 123.4(3) . . ?
C17 N13 C18 115.9(3) . . ?
C17 N13 H17 122.1 . . ?
C18 N13 H17 122.1 . . ?
N11 C11 C12 120.8(3) . . ?
N11 C11 C16 120.6(4) . . ?
C12 C11 C16 118.5(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 119.4(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 S11 120.5(3) . . ?
C13 C14 S11 119.4(3) . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N12 C17 N13 120.6(3) . . ?
N12 C17 S12 130.2(3) . . ?
N13 C17 S12 109.2(3) . . ?
C19 C18 N13 112.4(4) . . ?
C19 C18 H18 123.8 . . ?
N13 C18 H18 123.8 . . ?
C18 C19 S12 112.1(3) . . ?
C18 C19 H19 124.0 . . ?
S12 C19 H19 124.0 . . ?
C34 O31 C31 110.0(3) . . ?
C35 N31 C32 120.6(3) . . ?
C35 N31 C33 120.1(3) . . ?
C32 N31 C33 115.2(3) . . ?
O31 C31 C32 112.2(3) . . ?
O31 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
O31 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
N31 C32 C31 108.0(3) . . ?
N31 C32 H32A 110.1 . . ?
C31 C32 H32A 110.1 . . ?
N31 C32 H32B 110.1 . . ?
C31 C32 H32B 110.1 . . ?
H32A C32 H32B 108.4 . . ?
N31 C33 C34 108.4(3) . . ?
N31 C33 H33A 110.0 . . ?
C34 C33 H33A 110.0 . . ?
N31 C33 H33B 110.0 . . ?
C34 C33 H33B 110.0 . . ?
H33A C33 H33B 108.4 . . ?
O31 C34 C33 111.6(3) . . ?
O31 C34 H34A 109.3 . . ?
C33 C34 H34A 109.3 . . ?
O31 C34 H34B 109.3 . . ?
C33 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
N32 C35 N31 176.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 157.2(3) . . . . ?
O12 S11 N12 C17 28.8(3) . . . . ?
C14 S11 N12 C17 -88.3(3) . . . . ?
N11 C11 C12 C13 176.5(4) . . . . ?
C16 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C12 C13 C14 S11 175.9(3) . . . . ?
O11 S11 C14 C15 -164.7(3) . . . . ?
O12 S11 C14 C15 -36.5(3) . . . . ?
N12 S11 C14 C15 83.1(3) . . . . ?
O11 S11 C14 C13 19.6(3) . . . . ?
O12 S11 C14 C13 147.8(3) . . . . ?
N12 S11 C14 C13 -92.6(3) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
S11 C14 C15 C16 -175.1(3) . . . . ?
C14 C15 C16 C11 -1.0(6) . . . . ?
N11 C11 C16 C15 -175.7(3) . . . . ?
C12 C11 C16 C15 0.8(6) . . . . ?
S11 N12 C17 N13 178.1(3) . . . . ?
S11 N12 C17 S12 -0.9(5) . . . . ?
C18 N13 C17 N12 -179.4(3) . . . . ?
C18 N13 C17 S12 -0.3(4) . . . . ?
C19 S12 C17 N12 178.4(3) . . . . ?
C19 S12 C17 N13 -0.7(3) . . . . ?
C17 N13 C18 C19 1.4(5) . . . . ?
N13 C18 C19 S12 -1.9(4) . . . . ?
C17 S12 C19 C18 1.5(3) . . . . ?
C34 O31 C31 C32 61.4(4) . . . . ?
C35 N31 C32 C31 -151.4(4) . . . . ?
C33 N31 C32 C31 51.5(4) . . . . ?
O31 C31 C32 N31 -54.9(4) . . . . ?
C35 N31 C33 C34 150.7(3) . . . . ?
C32 N31 C33 C34 -52.1(4) . . . . ?
C31 O31 C34 C33 -61.5(4) . . . . ?
N31 C33 C34 O31 55.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.83(2) 2.16(3) 2.974(5) 166(3) 4_566 yes
N11 H11 O12 0.83(3) 2.18(3) 2.988(4) 166(4) 1_455 yes
N13 H17 O11 0.88 2.80 3.426(4) 129.7 3_656 yes
N13 H17 N12 0.88 1.95 2.826(4) 170.9 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_36
_database_code_depnum_ccdc_archive 'CCDC 2120797'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 9n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1,6-hexanenitrile (2:1) solvate'
_chemical_name_common            'Sulfathiazole, adiponitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C6 H8 N2'
_chemical_formula_sum            'C24 H26 N8 O4 S4'
_chemical_formula_weight         618.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.154(2)
_cell_length_b                   17.399(3)
_cell_length_c                   10.077(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.32(3)
_cell_angle_gamma                90
_cell_volume                     1401.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12559
_cell_measurement_theta_min      3.76
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.386
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12559
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.764
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_full        25.013
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2466
_reflns_number_gt                2136
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  9n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.45      40     44     90.9     4.25     490.7   36.23  0.0332  0.0248
3.45 - 2.32      89     90     98.9     5.43     299.2   41.07  0.0191  0.0199
2.32 - 1.84     128    128    100.0     5.48     164.7   38.41  0.0236  0.0188
1.84 - 1.59     129    129    100.0     5.62     152.2   38.20  0.0264  0.0195
1.59 - 1.44     128    128    100.0     5.62     104.9   33.97  0.0281  0.0214
1.44 - 1.34     131    131    100.0     5.57      98.3   30.60  0.0314  0.0225
1.34 - 1.26     129    129    100.0     5.57      86.6   28.46  0.0313  0.0247
1.26 - 1.20     127    127    100.0     5.49      78.6   26.53  0.0339  0.0286
1.20 - 1.14     143    143    100.0     5.50      83.9   25.80  0.0333  0.0277
1.14 - 1.10     118    118    100.0     5.46      72.4   24.67  0.0397  0.0309
1.10 - 1.06     130    130    100.0     5.71      49.6   20.32  0.0486  0.0358
1.06 - 1.02     142    142    100.0     5.44      51.2   19.98  0.0460  0.0366
1.02 - 0.99     155    155    100.0     5.43      34.2   16.04  0.0715  0.0450
0.99 - 0.97      90     90    100.0     5.23      31.9   14.42  0.0801  0.0496
0.97 - 0.94     169    169    100.0     4.72      34.4   13.49  0.0765  0.0528
0.94 - 0.92     107    107    100.0     4.86      24.9   11.61  0.0897  0.0652
0.92 - 0.90     138    138    100.0     4.21      18.6    8.76  0.0981  0.0827
0.90 - 0.88     148    148    100.0     4.05      19.8    8.30  0.1216  0.0906
0.88 - 0.87      78     78    100.0     3.82      18.6    7.46  0.1197  0.0966
0.87 - 0.85     166    166    100.0     3.48      21.7    7.57  0.1174  0.0993
0.85 - 0.84      84     84    100.0     3.15      23.4    7.50  0.1108  0.1024
#------------------------------------------------------------------------------
0.94 - 0.84     721    721    100.0     3.94      21.1    8.53  0.1082  0.0890
 Inf - 0.84    2569   2574     99.8     5.00      77.0   21.27  0.0375  0.0307
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.5492P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2466
_refine_ls_number_parameters     194
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.050

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.93783(5) 0.67577(2) 0.42279(5) 0.02337(15) Uani 1 1 d . . . . .
S12 S 0.86506(7) 0.65317(3) 0.73124(5) 0.03304(16) Uani 1 1 d . . . . .
O11 O 1.05558(16) 0.67234(7) 0.33389(14) 0.0312(3) Uani 1 1 d . . . . .
O12 O 0.94648(16) 0.73959(7) 0.51571(13) 0.0309(3) Uani 1 1 d . . . . .
N11 N 0.2564(2) 0.66212(11) 0.08850(19) 0.0369(4) Uani 1 1 d D . . . .
H10 H 0.184(3) 0.6922(12) 0.103(2) 0.050(7) Uiso 1 1 d D . . . .
H11 H 0.240(3) 0.6475(13) 0.0082(19) 0.047(7) Uiso 1 1 d D . . . .
N12 N 0.96030(18) 0.59441(8) 0.50125(14) 0.0228(3) Uani 1 1 d . . . . .
N13 N 0.91845(19) 0.51497(9) 0.67519(15) 0.0236(3) Uani 1 1 d . . . . .
H17 H 0.949(3) 0.4772(13) 0.631(2) 0.040(6) Uiso 1 1 d . . . . .
C11 C 0.4131(2) 0.66725(10) 0.16573(19) 0.0270(4) Uani 1 1 d . . . . .
C12 C 0.5474(2) 0.62812(12) 0.12690(19) 0.0300(4) Uani 1 1 d . . . . .
H12 H 0.528412 0.598828 0.045769 0.036 Uiso 1 1 calc R U . . .
C13 C 0.7053(2) 0.63179(11) 0.20470(18) 0.0274(4) Uani 1 1 d . . . . .
H13 H 0.794489 0.605137 0.176866 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7360(2) 0.67419(9) 0.32402(18) 0.0222(4) Uani 1 1 d . . . . .
C15 C 0.6047(2) 0.71252(10) 0.36518(19) 0.0267(4) Uani 1 1 d . . . . .
H15 H 0.624419 0.741061 0.447147 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4455(2) 0.70903(11) 0.2867(2) 0.0293(4) Uani 1 1 d . . . . .
H16 H 0.356595 0.735437 0.315412 0.035 Uiso 1 1 calc R U . . .
C17 C 0.9189(2) 0.58545(9) 0.62078(17) 0.0207(4) Uani 1 1 d . . . . .
C18 C 0.8779(2) 0.51200(12) 0.80191(19) 0.0310(4) Uani 1 1 d . . . . .
H18 H 0.874828 0.465918 0.851942 0.037 Uiso 1 1 calc R U . . .
C19 C 0.8436(3) 0.58117(12) 0.8457(2) 0.0370(5) Uani 1 1 d . . . . .
H19 H 0.811113 0.590109 0.929925 0.044 Uiso 1 1 calc R U . . .
N31 N 0.2907(2) 0.58776(12) 0.8130(2) 0.0472(5) Uani 1 1 d . . . . .
C31 C 0.3423(3) 0.58682(12) 0.7159(2) 0.0363(5) Uani 1 1 d . . . . .
C32 C 0.4087(3) 0.58316(12) 0.5911(2) 0.0358(5) Uani 1 1 d . . . . .
H32A H 0.504235 0.619022 0.598020 0.043 Uiso 1 1 calc R U . . .
H32B H 0.321081 0.599684 0.513922 0.043 Uiso 1 1 calc R U . . .
C33 C 0.4661(2) 0.50201(11) 0.56487(19) 0.0310(4) Uani 1 1 d . . . . .
H33A H 0.554259 0.485635 0.641817 0.037 Uiso 1 1 calc R U . . .
H33B H 0.370753 0.466101 0.558645 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.4373(14) . ?
S11 O12 1.4453(13) . ?
S11 N12 1.6142(15) . ?
S11 C14 1.748(2) . ?
S12 C19 1.735(2) . ?
S12 C17 1.7356(17) . ?
N11 C11 1.362(3) . ?
N11 H10 0.825(17) . ?
N11 H11 0.834(17) . ?
N12 C17 1.322(2) . ?
N13 C17 1.344(2) . ?
N13 C18 1.381(2) . ?
N13 H17 0.86(2) . ?
C11 C16 1.399(3) . ?
C11 C12 1.409(3) . ?
C12 C13 1.371(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(2) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.331(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C31 1.140(3) . ?
C31 C32 1.464(3) . ?
C32 C33 1.527(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.517(4) 3_666 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.82(8) . . ?
O11 S11 N12 104.09(8) . . ?
O12 S11 N12 111.72(8) . . ?
O11 S11 C14 108.29(8) . . ?
O12 S11 C14 107.56(8) . . ?
N12 S11 C14 105.59(8) . . ?
C19 S12 C17 90.44(9) . . ?
C11 N11 H10 119.0(15) . . ?
C11 N11 H11 121.6(15) . . ?
H10 N11 H11 112.6(16) . . ?
C17 N12 S11 121.65(12) . . ?
C17 N13 C18 115.59(15) . . ?
C17 N13 H17 117.4(15) . . ?
C18 N13 H17 126.9(15) . . ?
N11 C11 C16 121.82(17) . . ?
N11 C11 C12 120.21(18) . . ?
C16 C11 C12 117.95(18) . . ?
C13 C12 C11 120.85(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.57(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 119.53(17) . . ?
C13 C14 S11 119.36(14) . . ?
C15 C14 S11 121.07(14) . . ?
C16 C15 C14 119.96(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.12(17) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N12 C17 N13 120.07(15) . . ?
N12 C17 S12 130.26(13) . . ?
N13 C17 S12 109.66(13) . . ?
C19 C18 N13 112.14(17) . . ?
C19 C18 H18 123.9 . . ?
N13 C18 H18 123.9 . . ?
C18 C19 S12 112.17(14) . . ?
C18 C19 H19 123.9 . . ?
S12 C19 H19 123.9 . . ?
N31 C31 C32 178.3(2) . . ?
C31 C32 C33 111.52(17) . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
C33 C33 C32 111.6(2) 3_666 . ?
C33 C33 H33A 109.3 3_666 . ?
C32 C33 H33A 109.3 . . ?
C33 C33 H33B 109.3 3_666 . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 156.34(14) . . . . ?
O12 S11 N12 C17 26.93(17) . . . . ?
C14 S11 N12 C17 -89.71(15) . . . . ?
N11 C11 C12 C13 -178.99(18) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 S11 178.50(14) . . . . ?
O11 S11 C14 C13 34.05(16) . . . . ?
O12 S11 C14 C13 163.63(13) . . . . ?
N12 S11 C14 C13 -76.95(15) . . . . ?
O11 S11 C14 C15 -148.14(14) . . . . ?
O12 S11 C14 C15 -18.56(16) . . . . ?
N12 S11 C14 C15 100.86(15) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
S11 C14 C15 C16 -178.60(13) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
N11 C11 C16 C15 178.81(17) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
S11 N12 C17 N13 171.28(13) . . . . ?
S11 N12 C17 S12 -10.4(2) . . . . ?
C18 N13 C17 N12 178.31(16) . . . . ?
C18 N13 C17 S12 -0.34(19) . . . . ?
C19 S12 C17 N12 -178.78(18) . . . . ?
C19 S12 C17 N13 -0.31(14) . . . . ?
C17 N13 C18 C19 1.1(2) . . . . ?
N13 C18 C19 S12 -1.3(2) . . . . ?
C17 S12 C19 C18 0.92(17) . . . . ?
C31 C32 C33 C33 179.6(2) . . . 3_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.825(17) 2.292(19) 3.020(2) 147.5(19) 4_475 yes
N11 H11 N31 0.834(17) 2.330(18) 3.124(3) 159.3(19) 1_554 yes
N13 H17 O11 0.86(2) 2.63(2) 3.268(2) 132.2(18) 3_766 yes
N13 H17 N12 0.86(2) 2.06(2) 2.907(2) 167(2) 3_766 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_19
_database_code_depnum_ccdc_archive 'CCDC 2120783'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 20o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_19                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.00 angstrom. Data were integrated to 0.81
angstrom resolution, but this gives well below 50% observed at the 2sigma(I)
level. For the refinement, the data are truncated at 0.95 angstrom resolution.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 4-methylcyclohexanone (1:1) solvate'
_chemical_name_common            'Sulfathiazole, 4-methylcyclohexanone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C7 H12 O'
_chemical_formula_sum            'C16 H21 N3 O3 S2'
_chemical_formula_weight         367.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.572(1)
_cell_length_b                   12.959(3)
_cell_length_c                   21.533(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.48(3)
_cell_angle_gamma                90
_cell_volume                     1832.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15682
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      21.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.309
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15682
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_av_R_equivalents  0.1329
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.461
_diffrn_reflns_theta_max         21.965
_diffrn_reflns_theta_full        21.965
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2226
_reflns_number_gt                1470
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  20o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.40      57     58     98.3     5.93    1003.1   23.42  0.0389  0.0315
3.40 - 2.24     134    134    100.0     6.92     374.6   22.17  0.0603  0.0317
2.24 - 1.78     188    188    100.0     7.15     213.0   18.73  0.0786  0.0367
1.78 - 1.54     195    195    100.0     7.04     145.9   14.61  0.1048  0.0471
1.54 - 1.40     186    186    100.0     7.20      88.4   11.63  0.1381  0.0643
1.40 - 1.29     199    199    100.0     7.10      70.2    9.28  0.1637  0.0814
1.29 - 1.22     177    177    100.0     7.12      80.7    9.46  0.1538  0.0810
1.22 - 1.15     217    217    100.0     7.07      66.0    7.46  0.1738  0.0994
1.15 - 1.10     181    181    100.0     6.93      40.2    5.15  0.2664  0.1610
1.10 - 1.06     187    187    100.0     7.14      36.1    4.72  0.3002  0.1830
1.06 - 1.02     202    202    100.0     7.00      28.4    3.66  0.3702  0.2480
1.02 - 0.99     173    173    100.0     6.40      23.2    2.97  0.4490  0.3229
0.99 - 0.96     191    191    100.0     6.13      20.1    2.46  0.5011  0.4054
0.96 - 0.93     220    220    100.0     5.61      15.2    1.73  0.6062  0.5893
0.93 - 0.91     179    179    100.0     5.50      12.6    1.28  0.7036  0.7601
0.91 - 0.89     192    192    100.0     5.00      12.0    1.15  0.7184  0.8755
0.89 - 0.87     196    196    100.0     4.54      12.5    1.06  0.8066  0.9557
0.87 - 0.85     212    212    100.0     3.99       7.9    0.55  0.8634  1.7264
0.85 - 0.83     233    233    100.0     3.32       7.7    0.50  0.9078  2.0520
0.83 - 0.82     116    116    100.0     3.05       7.3    0.39  1.0149  2.4655
0.82 - 0.81     150    173     86.7     2.12      15.7    0.42  0.8378  1.4463
#--------------------------------------------------------------------------------
0.91 - 0.81    1099   1122     98.0     3.73      10.4    0.70  0.8317  1.4379
 Inf - 0.81    3785   3809     99.4     5.83      73.9    6.05  0.1589  0.1351
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The H atoms of the NH2 group are placed in-plane and allowed to ride.
This is an approximation.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.8940P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2226
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.051

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.32565(16) 0.44882(9) 0.13851(5) 0.0471(4) Uani 1 1 d . . . . .
S12 S 0.03516(17) 0.62155(10) 0.06968(6) 0.0534(4) Uani 1 1 d . . . . .
O11 O 0.4469(4) 0.3574(2) 0.14701(14) 0.0540(8) Uani 1 1 d . . . . .
O12 O 0.1112(4) 0.4414(2) 0.15003(14) 0.0520(8) Uani 1 1 d . . . . .
O30 O 0.8224(6) 0.8248(3) 0.10722(19) 0.0903(13) Uani 1 1 d . . . . .
N11 N 0.6552(6) 0.7858(3) 0.29717(18) 0.0635(12) Uani 1 1 d . . . . .
H10 H 0.785537 0.801511 0.297250 0.095 Uiso 1 1 calc R U . . .
H11 H 0.573365 0.820582 0.320777 0.095 Uiso 1 1 calc R U . . .
N12 N 0.3630(5) 0.4855(3) 0.06850(16) 0.0442(9) Uani 1 1 d . . . . .
N13 N 0.2934(5) 0.6009(3) -0.01234(17) 0.0466(10) Uani 1 1 d . . . . .
H17 H 0.397313 0.579430 -0.033284 0.070 Uiso 1 1 calc R U . . .
C11 C 0.5802(7) 0.7077(4) 0.2605(2) 0.0477(12) Uani 1 1 d . . . . .
C12 C 0.7057(7) 0.6510(4) 0.2225(2) 0.0486(12) Uani 1 1 d . . . . .
H12 H 0.846005 0.668279 0.221272 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6304(6) 0.5712(3) 0.1870(2) 0.0459(12) Uani 1 1 d . . . . .
H13 H 0.719191 0.532308 0.162383 0.055 Uiso 1 1 calc R U . . .
C14 C 0.4237(6) 0.5464(3) 0.18672(19) 0.0411(11) Uani 1 1 d . . . . .
C15 C 0.2971(6) 0.6038(4) 0.2237(2) 0.0462(12) Uani 1 1 d . . . . .
H15 H 0.155951 0.588037 0.223636 0.055 Uiso 1 1 calc R U . . .
C16 C 0.3728(6) 0.6822(4) 0.2602(2) 0.0494(12) Uani 1 1 d . . . . .
H16 H 0.284157 0.719919 0.285488 0.059 Uiso 1 1 calc R U . . .
C17 C 0.2488(6) 0.5599(4) 0.0430(2) 0.0451(11) Uani 1 1 d . . . . .
C18 C 0.1669(7) 0.6781(4) -0.0339(2) 0.0546(13) Uani 1 1 d . . . . .
H18 H 0.182682 0.713129 -0.072185 0.066 Uiso 1 1 calc R U . . .
C19 C 0.0192(7) 0.6987(4) 0.0048(2) 0.0572(13) Uani 1 1 d . . . . .
H19 H -0.082610 0.749784 -0.002646 0.069 Uiso 1 1 calc R U . . .
C30 C 0.6663(8) 0.8668(4) 0.1225(2) 0.0648(15) Uani 1 1 d . . . . .
C31 C 0.4601(8) 0.8265(4) 0.1036(3) 0.0701(15) Uani 1 1 d . . . . .
H31A H 0.393659 0.799684 0.140719 0.084 Uiso 1 1 calc R U . . .
H31B H 0.474333 0.768500 0.074163 0.084 Uiso 1 1 calc R U . . .
C32 C 0.3261(8) 0.9098(4) 0.0731(3) 0.0681(15) Uani 1 1 d . . . . .
H32A H 0.377596 0.926086 0.031649 0.082 Uiso 1 1 calc R U . . .
H32B H 0.185750 0.882851 0.066816 0.082 Uiso 1 1 calc R U . . .
C33 C 0.3208(7) 1.0074(4) 0.1110(2) 0.0667(15) Uani 1 1 d . . . . .
H33 H 0.254636 0.991351 0.150830 0.080 Uiso 1 1 calc R U . . .
C34 C 0.5350(8) 1.0460(4) 0.1266(2) 0.0689(15) Uani 1 1 d . . . . .
H34A H 0.527964 1.107396 0.153822 0.083 Uiso 1 1 calc R U . . .
H34B H 0.599185 1.067207 0.087888 0.083 Uiso 1 1 calc R U . . .
C35 C 0.6670(8) 0.9631(4) 0.1595(2) 0.0694(15) Uani 1 1 d . . . . .
H35A H 0.808386 0.988761 0.165476 0.083 Uiso 1 1 calc R U . . .
H35B H 0.614051 0.948731 0.200959 0.083 Uiso 1 1 calc R U . . .
C36 C 0.1944(9) 1.0892(5) 0.0768(3) 0.095(2) Uani 1 1 d . . . . .
H36A H 0.182079 1.149912 0.103595 0.142 Uiso 1 1 calc R U . . .
H36B H 0.058516 1.061671 0.066133 0.142 Uiso 1 1 calc R U . . .
H36C H 0.260940 1.109000 0.038766 0.142 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.436(3) . ?
S11 O12 1.445(3) . ?
S11 N12 1.610(4) . ?
S11 C14 1.742(4) . ?
S12 C19 1.718(5) . ?
S12 C17 1.735(4) . ?
O30 C30 1.219(5) . ?
N11 C11 1.363(5) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.326(5) . ?
N13 C17 1.348(5) . ?
N13 C18 1.369(5) . ?
N13 H17 0.8800 . ?
C11 C12 1.395(6) . ?
C11 C16 1.403(6) . ?
C12 C13 1.366(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(6) . ?
C15 C16 1.365(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.334(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C30 C35 1.481(7) . ?
C30 C31 1.492(7) . ?
C31 C32 1.524(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.507(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C36 1.518(7) . ?
C33 C34 1.518(7) . ?
C33 H33 1.0000 . ?
C34 C35 1.534(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.61(18) . . ?
O11 S11 N12 104.88(18) . . ?
O12 S11 N12 111.71(18) . . ?
O11 S11 C14 109.54(19) . . ?
O12 S11 C14 106.54(19) . . ?
N12 S11 C14 106.02(19) . . ?
C19 S12 C17 91.1(2) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 119.8(3) . . ?
C17 N13 C18 115.9(4) . . ?
C17 N13 H17 122.1 . . ?
C18 N13 H17 122.1 . . ?
N11 C11 C12 121.5(4) . . ?
N11 C11 C16 120.3(4) . . ?
C12 C11 C16 118.2(4) . . ?
C13 C12 C11 121.1(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 118.7(4) . . ?
C15 C14 S11 120.9(3) . . ?
C13 C14 S11 120.3(3) . . ?
C16 C15 C14 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N12 C17 N13 120.8(4) . . ?
N12 C17 S12 130.4(4) . . ?
N13 C17 S12 108.7(3) . . ?
C19 C18 N13 112.4(4) . . ?
C19 C18 H18 123.8 . . ?
N13 C18 H18 123.8 . . ?
C18 C19 S12 111.8(4) . . ?
C18 C19 H19 124.1 . . ?
S12 C19 H19 124.1 . . ?
O30 C30 C35 122.6(5) . . ?
O30 C30 C31 122.4(5) . . ?
C35 C30 C31 115.1(5) . . ?
C30 C31 C32 111.7(4) . . ?
C30 C31 H31A 109.3 . . ?
C32 C31 H31A 109.3 . . ?
C30 C31 H31B 109.3 . . ?
C32 C31 H31B 109.3 . . ?
H31A C31 H31B 107.9 . . ?
C33 C32 C31 112.8(4) . . ?
C33 C32 H32A 109.0 . . ?
C31 C32 H32A 109.0 . . ?
C33 C32 H32B 109.0 . . ?
C31 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
C32 C33 C36 110.4(4) . . ?
C32 C33 C34 110.7(4) . . ?
C36 C33 C34 111.1(5) . . ?
C32 C33 H33 108.2 . . ?
C36 C33 H33 108.2 . . ?
C34 C33 H33 108.2 . . ?
C33 C34 C35 111.8(4) . . ?
C33 C34 H34A 109.2 . . ?
C35 C34 H34A 109.2 . . ?
C33 C34 H34B 109.2 . . ?
C35 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C30 C35 C34 110.7(4) . . ?
C30 C35 H35A 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C30 C35 H35B 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 170.1(3) . . . . ?
O12 S11 N12 C17 41.6(4) . . . . ?
C14 S11 N12 C17 -74.0(4) . . . . ?
N11 C11 C12 C13 178.4(4) . . . . ?
C16 C11 C12 C13 -1.6(6) . . . . ?
C11 C12 C13 C14 1.8(7) . . . . ?
C12 C13 C14 C15 -0.7(6) . . . . ?
C12 C13 C14 S11 176.8(3) . . . . ?
O11 S11 C14 C15 -131.7(3) . . . . ?
O12 S11 C14 C15 -3.5(4) . . . . ?
N12 S11 C14 C15 115.6(4) . . . . ?
O11 S11 C14 C13 50.8(4) . . . . ?
O12 S11 C14 C13 179.0(3) . . . . ?
N12 S11 C14 C13 -61.9(4) . . . . ?
C13 C14 C15 C16 -0.6(6) . . . . ?
S11 C14 C15 C16 -178.1(3) . . . . ?
C14 C15 C16 C11 0.8(7) . . . . ?
N11 C11 C16 C15 -179.7(4) . . . . ?
C12 C11 C16 C15 0.3(6) . . . . ?
S11 N12 C17 N13 171.5(3) . . . . ?
S11 N12 C17 S12 -7.5(6) . . . . ?
C18 N13 C17 N12 -179.2(4) . . . . ?
C18 N13 C17 S12 0.1(5) . . . . ?
C19 S12 C17 N12 179.1(4) . . . . ?
C19 S12 C17 N13 0.0(3) . . . . ?
C17 N13 C18 C19 -0.1(6) . . . . ?
N13 C18 C19 S12 0.1(5) . . . . ?
C17 S12 C19 C18 -0.1(4) . . . . ?
O30 C30 C31 C32 -127.6(5) . . . . ?
C35 C30 C31 C32 50.7(6) . . . . ?
C30 C31 C32 C33 -50.7(6) . . . . ?
C31 C32 C33 C36 177.1(5) . . . . ?
C31 C32 C33 C34 53.6(6) . . . . ?
C32 C33 C34 C35 -55.2(6) . . . . ?
C36 C33 C34 C35 -178.3(4) . . . . ?
O30 C30 C35 C34 126.1(5) . . . . ?
C31 C30 C35 C34 -52.3(6) . . . . ?
C33 C34 C35 C30 54.1(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.88 2.21 2.978(5) 146.0 2_655 yes
N11 H11 O12 0.88 2.09 2.932(5) 158.9 2 yes
N13 H17 S11 0.88 2.99 3.828(4) 159.8 3_665 yes
N13 H17 N12 0.88 1.97 2.838(5) 170.3 3_665 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2120788'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 1o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_1                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.00 angstrom. Data were integrated to 0.84
angstrom resolution, but this gives well below 50% observed at the 2sigma(I)
level. For the refinement, the data are truncated at 0.95 angstrom resolution.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1,3 dimethyl-2-imidazolidone (2:1) solvate'
_chemical_name_common            'Sulfathiazole, dimethylethyleneurea solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H9 N3 O2 S2), C5 H10 N2 O'
_chemical_formula_sum            'C23 H28 N8 O5 S4'
_chemical_formula_weight         624.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.051(2)
_cell_length_b                   11.492(2)
_cell_length_c                   15.552(3)
_cell_angle_alpha                77.45(3)
_cell_angle_beta                 88.64(2)
_cell_angle_gamma                88.64(2)
_cell_volume                     1403.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10840
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      21.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.389
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10840
_diffrn_reflns_av_unetI/netI     0.1235
_diffrn_reflns_av_R_equivalents  0.1093
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.010
_diffrn_reflns_theta_max         21.966
_diffrn_reflns_theta_full        21.966
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3429
_reflns_number_gt                2079
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  1o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.40      75     77     97.4     3.29     451.6   19.50  0.0226  0.0423
3.40 - 2.29     169    169    100.0     3.27     154.8   14.90  0.0420  0.0485
2.29 - 1.82     249    249    100.0     3.28     112.3   12.89  0.0556  0.0558
1.82 - 1.58     245    245    100.0     3.20      67.5    9.07  0.0797  0.0769
1.58 - 1.44     243    243    100.0     3.23      54.4    7.40  0.0980  0.0941
1.44 - 1.33     266    266    100.0     3.16      50.0    6.61  0.1031  0.1093
1.33 - 1.26     218    218    100.0     3.27      39.5    5.20  0.1219  0.1352
1.26 - 1.20     245    245    100.0     3.11      43.3    5.65  0.1334  0.1411
1.20 - 1.14     263    263    100.0     3.18      35.6    4.54  0.1553  0.1684
1.14 - 1.10     244    244    100.0     3.06      32.1    3.85  0.1894  0.1995
1.10 - 1.06     255    255    100.0     3.10      25.9    3.31  0.2245  0.2432
1.06 - 1.03     221    221    100.0     3.14      18.6    2.64  0.2894  0.3197
1.03 - 1.00     240    240    100.0     3.09      17.1    2.27  0.3305  0.3744
1.00 - 0.97     292    292    100.0     3.05      14.1    1.84  0.3676  0.4707
0.97 - 0.95     204    204    100.0     3.11      12.6    1.70  0.3911  0.5417
0.95 - 0.92     350    351     99.7     3.04      11.4    1.52  0.4687  0.6278
0.92 - 0.90     244    244    100.0     2.82       9.4    1.08  0.5114  0.8506
0.90 - 0.89     138    139     99.3     2.73       8.7    1.01  0.5663  0.9684
0.89 - 0.87     288    290     99.3     2.33      10.5    1.04  0.5287  0.9154
0.87 - 0.85     333    342     97.4     2.04       7.6    0.64  0.6560  1.4849
0.85 - 0.84     108    147     73.5     1.32       7.5    0.64  0.6284  1.6828
#--------------------------------------------------------------------------------
0.94 - 0.84    1344   1396     96.3     2.39       9.1    0.97  0.5474  1.0317
 Inf - 0.84    4890   4944     98.9     2.94      41.5    4.50  0.1307  0.1741
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0143P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3429
_refine_ls_number_parameters     376
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.064

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.56454(16) 0.04286(11) 0.79468(9) 0.0299(4) Uani 1 1 d . . . . .
S12 S 0.70490(17) 0.27659(12) 0.86080(9) 0.0362(4) Uani 1 1 d . . . . .
O11 O 0.5273(4) -0.0797(3) 0.7965(2) 0.0357(9) Uani 1 1 d . . . . .
O12 O 0.7185(4) 0.0881(3) 0.7513(2) 0.0331(9) Uani 1 1 d . . . . .
N11 N 0.0024(6) 0.3472(4) 0.6362(3) 0.0421(13) Uani 1 1 d D . . . .
H10 H 0.036(6) 0.404(4) 0.595(2) 0.063 Uiso 1 1 d D U . . .
H11 H -0.076(5) 0.311(4) 0.619(3) 0.063 Uiso 1 1 d D U . . .
N12 N 0.5610(5) 0.0527(3) 0.8966(2) 0.0261(10) Uani 1 1 d . . . . .
N13 N 0.5788(4) 0.1619(3) 1.0035(3) 0.0304(11) Uani 1 1 d . . . . .
H17 H 0.530871 0.106044 1.043416 0.046 Uiso 1 1 calc R U . . .
C11 C 0.1356(6) 0.2764(5) 0.6716(3) 0.0281(13) Uani 1 1 d . . . . .
C12 C 0.1105(6) 0.1603(5) 0.7192(3) 0.0331(14) Uani 1 1 d . . . . .
H12 H 0.001414 0.129377 0.727043 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2427(6) 0.0910(4) 0.7546(3) 0.0306(13) Uani 1 1 d . . . . .
H13 H 0.223890 0.011990 0.786741 0.037 Uiso 1 1 calc R U . . .
C14 C 0.4033(6) 0.1329(4) 0.7449(3) 0.0239(12) Uani 1 1 d . . . . .
C15 C 0.4294(6) 0.2482(4) 0.6974(3) 0.0273(13) Uani 1 1 d . . . . .
H15 H 0.538962 0.278189 0.689680 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2987(6) 0.3192(4) 0.6615(3) 0.0293(13) Uani 1 1 d . . . . .
H16 H 0.318342 0.398132 0.629455 0.035 Uiso 1 1 calc R U . . .
C17 C 0.6068(6) 0.1507(4) 0.9209(3) 0.0267(13) Uani 1 1 d . . . . .
C18 C 0.6306(6) 0.2685(5) 1.0220(4) 0.0408(15) Uani 1 1 d . . . . .
H18 H 0.619173 0.287653 1.078343 0.049 Uiso 1 1 calc R U . . .
C19 C 0.6974(6) 0.3397(5) 0.9523(4) 0.0383(15) Uani 1 1 d . . . . .
H19 H 0.736937 0.416967 0.952356 0.046 Uiso 1 1 calc R U . . .
S21 S 0.18730(17) 0.68560(12) 0.57279(9) 0.0377(4) Uani 1 1 d . . . . .
S22 S 0.22580(19) 0.96217(13) 0.58039(10) 0.0466(5) Uani 1 1 d . . . . .
O21 O 0.1370(4) 0.5805(3) 0.5438(2) 0.0494(11) Uani 1 1 d . . . . .
O22 O 0.0797(4) 0.7273(3) 0.6354(2) 0.0449(10) Uani 1 1 d . . . . .
C21 C 0.6800(6) 0.5748(4) 0.7070(3) 0.0275(13) Uani 1 1 d . . . . .
N21 N 0.8206(5) 0.5296(4) 0.7515(3) 0.0373(12) Uani 1 1 d D . . . .
H20 H 0.848(5) 0.560(4) 0.794(2) 0.056 Uiso 1 1 d D U . . .
H21 H 0.905(4) 0.519(5) 0.720(3) 0.056 Uiso 1 1 d D U . . .
N22 N 0.2170(5) 0.7847(3) 0.4834(3) 0.0293(11) Uani 1 1 d . . . . .
N23 N 0.2687(5) 0.9803(4) 0.4169(3) 0.0358(11) Uani 1 1 d . . . . .
H27 H 0.275034 0.964137 0.364138 0.054 Uiso 1 1 calc R U . . .
C22 C 0.6576(6) 0.5690(4) 0.6190(3) 0.0348(14) Uani 1 1 d . . . . .
H22 H 0.744400 0.537864 0.587583 0.042 Uiso 1 1 calc R U . . .
C23 C 0.5121(7) 0.6077(4) 0.5778(3) 0.0335(14) Uani 1 1 d . . . . .
H23 H 0.499529 0.604221 0.517809 0.040 Uiso 1 1 calc R U . . .
C24 C 0.3818(6) 0.6523(4) 0.6226(3) 0.0293(13) Uani 1 1 d . . . . .
C25 C 0.4045(7) 0.6610(5) 0.7091(4) 0.0398(15) Uani 1 1 d . . . . .
H25 H 0.318410 0.693654 0.740025 0.048 Uiso 1 1 calc R U . . .
C26 C 0.5517(7) 0.6224(5) 0.7505(4) 0.0411(15) Uani 1 1 d . . . . .
H26 H 0.565556 0.628469 0.809822 0.049 Uiso 1 1 calc R U . . .
C27 C 0.2350(6) 0.8959(5) 0.4896(3) 0.0309(13) Uani 1 1 d . . . . .
C28 C 0.2925(6) 1.0934(5) 0.4300(4) 0.0412(15) Uani 1 1 d . . . . .
H28 H 0.318102 1.160102 0.384090 0.049 Uiso 1 1 calc R U . . .
C29 C 0.2756(7) 1.0986(5) 0.5144(4) 0.0530(17) Uani 1 1 d . . . . .
H29 H 0.289268 1.169089 0.535820 0.064 Uiso 1 1 calc R U . . .
O31 O 0.8461(5) 0.5994(3) 0.9222(2) 0.0527(11) Uani 1 1 d . . . . .
N31 N 0.9015(6) 0.7991(4) 0.8989(3) 0.0473(13) Uani 1 1 d . . . . .
N32 N 0.8610(6) 0.7006(5) 1.0349(3) 0.0595(15) Uani 1 1 d . . . . .
C31 C 0.9605(7) 0.8147(5) 0.8094(4) 0.0561(18) Uani 1 1 d . . . . .
H31A H 0.906514 0.757559 0.781128 0.084 Uiso 1 1 calc R U . . .
H31B H 1.081083 0.801114 0.808479 0.084 Uiso 1 1 calc R U . . .
H31C H 0.934111 0.896044 0.777345 0.084 Uiso 1 1 calc R U . . .
C32 C 0.9441(7) 0.8823(5) 0.9520(5) 0.0588(19) Uani 1 1 d . . . . .
H32A H 0.891419 0.961528 0.929830 0.071 Uiso 1 1 calc R U . . .
H32B H 1.065896 0.891102 0.953583 0.071 Uiso 1 1 calc R U . . .
C33 C 0.8743(7) 0.8237(6) 1.0412(5) 0.068(2) Uani 1 1 d . . . . .
H33A H 0.950222 0.831496 1.088672 0.081 Uiso 1 1 calc R U . . .
H33B H 0.764209 0.858447 1.052193 0.081 Uiso 1 1 calc R U . . .
C34 C 0.7964(8) 0.6085(7) 1.1036(4) 0.085(2) Uani 1 1 d . . . . .
H34A H 0.826066 0.530580 1.091080 0.127 Uiso 1 1 calc R U . . .
H34B H 0.675174 0.617165 1.106886 0.127 Uiso 1 1 calc R U . . .
H34C H 0.843663 0.614639 1.159883 0.127 Uiso 1 1 calc R U . . .
C35 C 0.8666(7) 0.6916(6) 0.9493(4) 0.0440(16) Uani 1 1 d . . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.441(3) . ?
S11 O12 1.449(3) . ?
S11 N12 1.613(4) . ?
S11 C14 1.729(5) . ?
S12 C19 1.732(5) . ?
S12 C17 1.738(5) . ?
N11 C11 1.381(6) . ?
N11 H10 0.86(2) . ?
N11 H11 0.85(2) . ?
N12 C17 1.326(5) . ?
N13 C17 1.331(6) . ?
N13 C18 1.393(6) . ?
N13 H17 0.8800 . ?
C11 C12 1.396(7) . ?
C11 C16 1.406(6) . ?
C12 C13 1.367(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(6) . ?
C15 C16 1.368(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.320(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S21 O22 1.440(3) . ?
S21 O21 1.447(3) . ?
S21 N22 1.611(4) . ?
S21 C24 1.761(5) . ?
S22 C29 1.728(6) . ?
S22 C27 1.744(5) . ?
C21 N21 1.372(6) . ?
C21 C26 1.387(6) . ?
C21 C22 1.401(6) . ?
N21 H20 0.85(2) . ?
N21 H21 0.85(2) . ?
N22 C27 1.314(6) . ?
N23 C27 1.347(6) . ?
N23 C28 1.378(6) . ?
N23 H27 0.8800 . ?
C22 C23 1.367(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.394(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(6) . ?
C25 C26 1.379(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C28 C29 1.330(7) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
O31 C35 1.237(6) . ?
N31 C35 1.343(7) . ?
N31 C31 1.436(6) . ?
N31 C32 1.443(6) . ?
N32 C35 1.358(6) . ?
N32 C34 1.428(7) . ?
N32 C33 1.446(7) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.506(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.2(2) . . ?
O11 S11 N12 105.0(2) . . ?
O12 S11 N12 110.86(19) . . ?
O11 S11 C14 108.9(2) . . ?
O12 S11 C14 108.0(2) . . ?
N12 S11 C14 106.4(2) . . ?
C19 S12 C17 90.2(3) . . ?
C11 N11 H10 110(4) . . ?
C11 N11 H11 115(4) . . ?
H10 N11 H11 110.7(18) . . ?
C17 N12 S11 121.8(4) . . ?
C17 N13 C18 115.2(4) . . ?
C17 N13 H17 122.4 . . ?
C18 N13 H17 122.4 . . ?
N11 C11 C12 120.3(5) . . ?
N11 C11 C16 121.3(5) . . ?
C12 C11 C16 118.4(5) . . ?
C13 C12 C11 120.0(5) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 121.7(5) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 118.6(4) . . ?
C13 C14 S11 119.5(4) . . ?
C15 C14 S11 121.8(4) . . ?
C16 C15 C14 120.6(5) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N12 C17 N13 119.8(4) . . ?
N12 C17 S12 130.3(4) . . ?
N13 C17 S12 110.0(4) . . ?
C19 C18 N13 112.1(5) . . ?
C19 C18 H18 123.9 . . ?
N13 C18 H18 123.9 . . ?
C18 C19 S12 112.4(4) . . ?
C18 C19 H19 123.8 . . ?
S12 C19 H19 123.8 . . ?
O22 S21 O21 117.1(2) . . ?
O22 S21 N22 113.0(2) . . ?
O21 S21 N22 104.9(2) . . ?
O22 S21 C24 107.0(2) . . ?
O21 S21 C24 107.2(2) . . ?
N22 S21 C24 107.2(2) . . ?
C29 S22 C27 90.9(3) . . ?
N21 C21 C26 119.9(5) . . ?
N21 C21 C22 121.8(5) . . ?
C26 C21 C22 118.2(5) . . ?
C21 N21 H20 117(3) . . ?
C21 N21 H21 116(3) . . ?
H20 N21 H21 111.1(18) . . ?
C27 N22 S21 118.2(4) . . ?
C27 N23 C28 116.1(4) . . ?
C27 N23 H27 122.0 . . ?
C28 N23 H27 122.0 . . ?
C23 C22 C21 120.7(5) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.8(5) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 118.8(5) . . ?
C25 C24 S21 120.8(4) . . ?
C23 C24 S21 120.2(4) . . ?
C26 C25 C24 120.2(5) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 121.2(5) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
N22 C27 N23 120.0(5) . . ?
N22 C27 S22 131.3(4) . . ?
N23 C27 S22 108.7(4) . . ?
C29 C28 N23 112.2(5) . . ?
C29 C28 H28 123.9 . . ?
N23 C28 H28 123.9 . . ?
C28 C29 S22 112.1(4) . . ?
C28 C29 H29 124.0 . . ?
S22 C29 H29 124.0 . . ?
C35 N31 C31 122.6(5) . . ?
C35 N31 C32 111.4(5) . . ?
C31 N31 C32 120.8(5) . . ?
C35 N32 C34 122.3(6) . . ?
C35 N32 C33 110.5(6) . . ?
C34 N32 C33 124.2(5) . . ?
N31 C31 H31A 109.5 . . ?
N31 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N31 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N31 C32 C33 102.1(5) . . ?
N31 C32 H32A 111.3 . . ?
C33 C32 H32A 111.3 . . ?
N31 C32 H32B 111.3 . . ?
C33 C32 H32B 111.3 . . ?
H32A C32 H32B 109.2 . . ?
N32 C33 C32 102.8(5) . . ?
N32 C33 H33A 111.2 . . ?
C32 C33 H33A 111.2 . . ?
N32 C33 H33B 111.2 . . ?
C32 C33 H33B 111.2 . . ?
H33A C33 H33B 109.1 . . ?
N32 C34 H34A 109.5 . . ?
N32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O31 C35 N31 125.7(5) . . ?
O31 C35 N32 125.8(6) . . ?
N31 C35 N32 108.5(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 172.9(4) . . . . ?
O12 S11 N12 C17 45.5(4) . . . . ?
C14 S11 N12 C17 -71.7(4) . . . . ?
N11 C11 C12 C13 -179.5(4) . . . . ?
C16 C11 C12 C13 -0.1(7) . . . . ?
C11 C12 C13 C14 0.2(7) . . . . ?
C12 C13 C14 C15 -0.4(7) . . . . ?
C12 C13 C14 S11 177.6(4) . . . . ?
O11 S11 C14 C13 32.6(4) . . . . ?
O12 S11 C14 C13 160.8(4) . . . . ?
N12 S11 C14 C13 -80.1(4) . . . . ?
O11 S11 C14 C15 -149.5(4) . . . . ?
O12 S11 C14 C15 -21.3(4) . . . . ?
N12 S11 C14 C15 97.8(4) . . . . ?
C13 C14 C15 C16 0.5(7) . . . . ?
S11 C14 C15 C16 -177.4(3) . . . . ?
C14 C15 C16 C11 -0.4(7) . . . . ?
N11 C11 C16 C15 179.6(4) . . . . ?
C12 C11 C16 C15 0.2(7) . . . . ?
S11 N12 C17 N13 169.9(3) . . . . ?
S11 N12 C17 S12 -10.4(6) . . . . ?
C18 N13 C17 N12 -179.6(4) . . . . ?
C18 N13 C17 S12 0.7(5) . . . . ?
C19 S12 C17 N12 178.9(5) . . . . ?
C19 S12 C17 N13 -1.3(4) . . . . ?
C17 N13 C18 C19 0.7(7) . . . . ?
N13 C18 C19 S12 -1.7(6) . . . . ?
C17 S12 C19 C18 1.8(5) . . . . ?
O22 S21 N22 C27 39.3(4) . . . . ?
O21 S21 N22 C27 168.0(4) . . . . ?
C24 S21 N22 C27 -78.3(4) . . . . ?
N21 C21 C22 C23 175.8(5) . . . . ?
C26 C21 C22 C23 -0.9(7) . . . . ?
C21 C22 C23 C24 -0.9(8) . . . . ?
C22 C23 C24 C25 2.4(8) . . . . ?
C22 C23 C24 S21 -172.6(4) . . . . ?
O22 S21 C24 C25 4.1(5) . . . . ?
O21 S21 C24 C25 -122.3(4) . . . . ?
N22 S21 C24 C25 125.5(4) . . . . ?
O22 S21 C24 C23 179.0(4) . . . . ?
O21 S21 C24 C23 52.6(5) . . . . ?
N22 S21 C24 C23 -59.6(4) . . . . ?
C23 C24 C25 C26 -2.1(8) . . . . ?
S21 C24 C25 C26 172.9(4) . . . . ?
C24 C25 C26 C21 0.3(8) . . . . ?
N21 C21 C26 C25 -175.5(5) . . . . ?
C22 C21 C26 C25 1.2(8) . . . . ?
S21 N22 C27 N23 176.6(3) . . . . ?
S21 N22 C27 S22 -2.6(6) . . . . ?
C28 N23 C27 N22 -177.3(4) . . . . ?
C28 N23 C27 S22 2.0(5) . . . . ?
C29 S22 C27 N22 177.2(5) . . . . ?
C29 S22 C27 N23 -2.0(4) . . . . ?
C27 N23 C28 C29 -0.7(7) . . . . ?
N23 C28 C29 S22 -1.0(6) . . . . ?
C27 S22 C29 C28 1.7(5) . . . . ?
C35 N31 C32 C33 -18.7(6) . . . . ?
C31 N31 C32 C33 -173.6(5) . . . . ?
C35 N32 C33 C32 -17.9(6) . . . . ?
C34 N32 C33 C32 -178.5(5) . . . . ?
N31 C32 C33 N32 20.9(6) . . . . ?
C31 N31 C35 O31 -16.2(9) . . . . ?
C32 N31 C35 O31 -170.6(5) . . . . ?
C31 N31 C35 N32 162.6(5) . . . . ?
C32 N31 C35 N32 8.2(7) . . . . ?
C34 N32 C35 O31 -13.3(9) . . . . ?
C33 N32 C35 O31 -174.4(5) . . . . ?
C34 N32 C35 N31 167.9(6) . . . . ?
C33 N32 C35 N31 6.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O21 0.86(2) 2.18(3) 2.969(6) 154(4) . yes
N11 H10 O21 0.86(2) 2.57(4) 2.980(5) 111(3) 2_566 yes
N11 H11 N22 0.85(2) 2.43(3) 3.223(6) 155(4) 2_566 yes
N13 H17 O11 0.88 2.48 3.152(5) 134.0 2_657 yes
N13 H17 N12 0.88 2.01 2.855(5) 160.7 2_657 yes
N21 H20 O31 0.85(2) 2.13(3) 2.949(6) 160(4) . yes
N21 H21 N11 0.85(2) 2.69(4) 3.333(6) 134(4) 1_655 yes
N23 H27 O12 0.88 2.01 2.890(5) 174.6 2_666 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_25
_database_code_depnum_ccdc_archive 'CCDC 2120786'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 26o
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, tetrahydrofuran (1:1) solvate'
_chemical_name_common            'Sulfathiazole, tetrahydrofuran solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H8 O'
_chemical_formula_sum            'C13 H17 N3 O3 S2'
_chemical_formula_weight         327.41
_chemical_absolute_configuration unk


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.515(2)
_cell_length_b                   16.675(3)
_cell_length_c                   19.249(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3054.1(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    20973
_cell_measurement_theta_min      1.62
_cell_measurement_theta_max      30.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.362
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20973
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.616
_diffrn_reflns_theta_max         30.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8806
_reflns_number_gt                6994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  26o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.14      76     80     95.0     4.55     544.4   29.84  0.0344  0.0379
3.14 - 2.05     177    177    100.0     5.90     298.7   31.94  0.0444  0.0317
2.05 - 1.58     252    252    100.0     6.23     154.7   32.57  0.0398  0.0272
1.58 - 1.37     256    256    100.0     6.38     107.8   30.07  0.0504  0.0299
1.37 - 1.24     252    252    100.0     6.38      83.5   26.86  0.0566  0.0307
1.24 - 1.14     273    273    100.0     6.43      97.2   26.25  0.0590  0.0340
1.14 - 1.07     244    244    100.0     6.30      62.7   22.43  0.0825  0.0370
1.07 - 1.01     285    285    100.0     5.24      45.8   18.38  0.0848  0.0447
1.01 - 0.97     214    215     99.5     4.81      33.4   15.62  0.0964  0.0550
0.97 - 0.93     269    269    100.0     4.46      32.5   14.32  0.1085  0.0588
0.93 - 0.90     224    224    100.0     4.00      30.7   12.45  0.1062  0.0658
0.90 - 0.87     254    254    100.0     3.56      23.5   10.52  0.1151  0.0803
0.87 - 0.84     302    304     99.3     2.97      22.6    8.62  0.1045  0.0942
0.84 - 0.82     222    222    100.0     2.93      19.9    7.49  0.1313  0.1105
0.82 - 0.80     225    225    100.0     2.88      18.1    6.58  0.1436  0.1279
0.80 - 0.78     269    286     94.1     2.62      16.6    5.71  0.1650  0.1461
0.78 - 0.76     270    298     90.6     2.51      14.2    5.06  0.1997  0.1764
0.76 - 0.74     295    309     95.5     2.48      14.5    4.34  0.2229  0.1983
0.74 - 0.73     177    185     95.7     2.51      13.0    3.94  0.2518  0.2233
0.73 - 0.71     339    394     86.0     1.99      11.9    3.57  0.2291  0.2538
0.71 - 0.70     164    211     77.7     1.27      11.7    2.58  0.3325  0.4049
#------------------------------------------------------------------------------
0.80 - 0.70    1514   1683     90.0     2.25      13.8    4.30  0.2140  0.2157
 Inf - 0.70    5039   5215     96.6     4.03      59.9   14.56  0.0626  0.0524
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          'Refined as a 2-component inversion twin.'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+0.5297P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.46(7)
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_number_reflns         8806
_refine_ls_number_parameters     393
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.061

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.62599(7) 0.48416(4) 0.31311(3) 0.02226(15) Uani 1 1 d . . . . .
S12 S 0.28372(8) 0.51898(5) 0.30136(4) 0.02963(17) Uani 1 1 d . . . . .
O11 O 0.7681(2) 0.50806(12) 0.32926(11) 0.0286(5) Uani 1 1 d . . . . .
O12 O 0.5678(2) 0.51102(13) 0.24771(10) 0.0293(5) Uani 1 1 d . . . . .
N11 N 0.5716(3) 0.13344(16) 0.33922(16) 0.0349(7) Uani 1 1 d D . . . .
H10 H 0.519(3) 0.1060(18) 0.3127(18) 0.052 Uiso 1 1 d D U . . .
H11 H 0.637(3) 0.1052(18) 0.3564(19) 0.052 Uiso 1 1 d D U . . .
N12 N 0.5333(2) 0.51625(15) 0.37764(11) 0.0226(5) Uani 1 1 d . . . . .
N13 N 0.3184(2) 0.53548(15) 0.43064(13) 0.0257(6) Uani 1 1 d . . . . .
H17 H 0.356616 0.538687 0.472174 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5891(3) 0.21409(17) 0.32988(15) 0.0251(6) Uani 1 1 d . . . . .
C12 C 0.6999(3) 0.25479(17) 0.36225(16) 0.0258(6) Uani 1 1 d . . . . .
H12 H 0.766608 0.225798 0.389049 0.031 Uiso 1 1 calc R U . . .
C13 C 0.7127(3) 0.33705(17) 0.35534(15) 0.0239(6) Uani 1 1 d . . . . .
H13 H 0.787321 0.364537 0.377870 0.029 Uiso 1 1 calc R U . . .
C14 C 0.6166(3) 0.37935(16) 0.31554(15) 0.0224(6) Uani 1 1 d . . . . .
C15 C 0.5073(3) 0.33986(18) 0.28189(15) 0.0248(6) Uani 1 1 d . . . . .
H15 H 0.442810 0.368948 0.253895 0.030 Uiso 1 1 calc R U . . .
C16 C 0.4936(3) 0.25783(18) 0.28961(15) 0.0266(7) Uani 1 1 d . . . . .
H16 H 0.418345 0.230756 0.267241 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3944(3) 0.52212(17) 0.37355(14) 0.0224(5) Uani 1 1 d . . . . .
C18 C 0.1761(3) 0.54389(19) 0.42015(17) 0.0297(7) Uani 1 1 d . . . . .
H18 H 0.111165 0.554480 0.456507 0.036 Uiso 1 1 calc R U . . .
C19 C 0.1385(3) 0.53569(19) 0.35381(17) 0.0319(7) Uani 1 1 d . . . . .
H19 H 0.044471 0.538617 0.337414 0.038 Uiso 1 1 calc R U . . .
S21 S 0.37134(7) 0.52293(4) 0.62707(4) 0.02167(15) Uani 1 1 d . . . . .
S22 S 0.71801(8) 0.51273(5) 0.63384(4) 0.02818(17) Uani 1 1 d . . . . .
O21 O 0.2314(2) 0.50841(12) 0.60023(11) 0.0280(5) Uani 1 1 d . . . . .
O22 O 0.4270(2) 0.46638(12) 0.67696(11) 0.0292(5) Uani 1 1 d . . . . .
N21 N 0.3807(3) 0.84694(16) 0.75142(16) 0.0368(7) Uani 1 1 d D . . . .
H20 H 0.440(3) 0.862(2) 0.7804(17) 0.055 Uiso 1 1 d D U . . .
H21 H 0.345(4) 0.8846(18) 0.7284(17) 0.055 Uiso 1 1 d D U . . .
N22 N 0.4690(2) 0.52692(15) 0.55841(11) 0.0217(5) Uani 1 1 d . . . . .
N23 N 0.6841(2) 0.52202(16) 0.50391(12) 0.0270(5) Uani 1 1 d . . . . .
H27 H 0.645660 0.525606 0.462460 0.041 Uiso 1 1 calc R U . . .
C21 C 0.3803(3) 0.77199(17) 0.72276(15) 0.0247(6) Uani 1 1 d . . . . .
C22 C 0.2988(3) 0.75587(17) 0.66399(15) 0.0253(6) Uani 1 1 d . . . . .
H22 H 0.245221 0.797718 0.643485 0.030 Uiso 1 1 calc R U . . .
C23 C 0.2950(3) 0.67961(16) 0.63513(15) 0.0219(6) Uani 1 1 d . . . . .
H23 H 0.239341 0.669336 0.595122 0.026 Uiso 1 1 calc R U . . .
C24 C 0.3737(3) 0.61802(16) 0.66545(14) 0.0206(6) Uani 1 1 d . . . . .
C25 C 0.4552(3) 0.63323(18) 0.72385(15) 0.0251(6) Uani 1 1 d . . . . .
H25 H 0.508859 0.591321 0.744208 0.030 Uiso 1 1 calc R U . . .
C26 C 0.4583(3) 0.70922(19) 0.75235(16) 0.0268(6) Uani 1 1 d . . . . .
H26 H 0.513862 0.719127 0.792449 0.032 Uiso 1 1 calc R U . . .
C27 C 0.6077(3) 0.52162(18) 0.56197(14) 0.0213(5) Uani 1 1 d . . . . .
C28 C 0.8277(3) 0.5164(2) 0.51314(17) 0.0343(7) Uani 1 1 d . . . . .
H28 H 0.893254 0.515514 0.475937 0.041 Uiso 1 1 calc R U . . .
C29 C 0.8647(3) 0.5124(2) 0.58061(17) 0.0328(7) Uani 1 1 d . . . . .
H29 H 0.958924 0.509750 0.596829 0.039 Uiso 1 1 calc R U . . .
O30 O 0.0073(3) 0.26496(15) 0.43238(14) 0.0439(6) Uani 1 1 d . . . . .
C30 C 0.0901(4) 0.1973(2) 0.4512(2) 0.0447(9) Uani 1 1 d . . . . .
H30A H 0.061869 0.149643 0.423884 0.054 Uiso 1 1 calc R U . . .
H30B H 0.078997 0.185073 0.501188 0.054 Uiso 1 1 calc R U . . .
C31 C 0.2394(4) 0.2202(3) 0.4352(2) 0.0541(11) Uani 1 1 d . . . . .
H31A H 0.267366 0.201010 0.388540 0.065 Uiso 1 1 calc R U . . .
H31B H 0.304672 0.197475 0.470143 0.065 Uiso 1 1 calc R U . . .
C32 C 0.2392(4) 0.3113(3) 0.4382(2) 0.0561(11) Uani 1 1 d . . . . .
H32A H 0.298420 0.330835 0.476961 0.067 Uiso 1 1 calc R U . . .
H32B H 0.274401 0.334436 0.394171 0.067 Uiso 1 1 calc R U . . .
C33 C 0.0883(4) 0.3330(2) 0.4496(2) 0.0528(11) Uani 1 1 d . . . . .
H33A H 0.072556 0.348137 0.498746 0.063 Uiso 1 1 calc R U . . .
H33B H 0.061762 0.378963 0.419807 0.063 Uiso 1 1 calc R U . . .
O40 O 0.2298(2) 0.71872(15) 0.46934(12) 0.0396(6) Uani 1 1 d . . . . .
C40 C 0.3731(4) 0.7435(2) 0.4666(2) 0.0456(9) Uani 1 1 d . . . . .
H40A H 0.434127 0.703352 0.489447 0.055 Uiso 1 1 calc R U . . .
H40B H 0.385156 0.795627 0.490499 0.055 Uiso 1 1 calc R U . . .
C41 C 0.4111(4) 0.7513(3) 0.3904(2) 0.0477(10) Uani 1 1 d . . . . .
H41A H 0.468811 0.705148 0.375035 0.057 Uiso 1 1 calc R U . . .
H41B H 0.464030 0.801389 0.381777 0.057 Uiso 1 1 calc R U . . .
C42 C 0.2710(3) 0.7525(2) 0.35278(17) 0.0360(8) Uani 1 1 d . . . . .
H42A H 0.263192 0.800221 0.322422 0.043 Uiso 1 1 calc R U . . .
H42B H 0.258536 0.703607 0.324258 0.043 Uiso 1 1 calc R U . . .
C43 C 0.1644(4) 0.7556(2) 0.41093(17) 0.0342(8) Uani 1 1 d . . . . .
H43A H 0.139071 0.811885 0.421676 0.041 Uiso 1 1 calc R U . . .
H43B H 0.077962 0.726260 0.397771 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.444(2) . ?
S11 O12 1.447(2) . ?
S11 N12 1.614(2) . ?
S11 C14 1.751(3) . ?
S12 C19 1.734(3) . ?
S12 C17 1.745(3) . ?
N11 C11 1.367(4) . ?
N11 H10 0.85(2) . ?
N11 H11 0.85(2) . ?
N12 C17 1.327(3) . ?
N13 C17 1.335(4) . ?
N13 C18 1.376(4) . ?
N13 H17 0.8800 . ?
C11 C16 1.399(4) . ?
C11 C12 1.401(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(4) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.333(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S21 O22 1.446(2) . ?
S21 O21 1.448(2) . ?
S21 N22 1.617(2) . ?
S21 C24 1.749(3) . ?
S22 C29 1.732(3) . ?
S22 C27 1.743(3) . ?
N21 C21 1.366(4) . ?
N21 H20 0.84(2) . ?
N21 H21 0.84(2) . ?
N22 C27 1.324(3) . ?
N23 C27 1.334(4) . ?
N23 C28 1.380(4) . ?
N23 H27 0.8800 . ?
C21 C22 1.398(4) . ?
C21 C26 1.404(4) . ?
C22 C23 1.388(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.399(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(4) . ?
C25 C26 1.381(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C28 C29 1.347(4) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
O30 C33 1.411(4) . ?
O30 C30 1.422(4) . ?
C30 C31 1.503(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.521(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.497(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
O40 C43 1.425(4) . ?
O40 C40 1.426(4) . ?
C40 C41 1.516(5) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.517(5) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.512(4) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.43(13) . . ?
O11 S11 N12 104.74(12) . . ?
O12 S11 N12 110.97(12) . . ?
O11 S11 C14 108.53(13) . . ?
O12 S11 C14 108.22(13) . . ?
N12 S11 C14 106.41(13) . . ?
C19 S12 C17 90.72(14) . . ?
C11 N11 H10 122(2) . . ?
C11 N11 H11 121(2) . . ?
H10 N11 H11 111(2) . . ?
C17 N12 S11 121.50(19) . . ?
C17 N13 C18 115.4(3) . . ?
C17 N13 H17 122.3 . . ?
C18 N13 H17 122.3 . . ?
N11 C11 C16 120.5(3) . . ?
N11 C11 C12 120.6(3) . . ?
C16 C11 C12 118.9(3) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 S11 119.3(2) . . ?
C15 C14 S11 119.9(2) . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N12 C17 N13 120.2(2) . . ?
N12 C17 S12 130.2(2) . . ?
N13 C17 S12 109.5(2) . . ?
C19 C18 N13 113.2(3) . . ?
C19 C18 H18 123.4 . . ?
N13 C18 H18 123.4 . . ?
C18 C19 S12 111.1(2) . . ?
C18 C19 H19 124.4 . . ?
S12 C19 H19 124.4 . . ?
O22 S21 O21 117.67(13) . . ?
O22 S21 N22 111.05(13) . . ?
O21 S21 N22 104.09(12) . . ?
O22 S21 C24 107.81(13) . . ?
O21 S21 C24 108.29(13) . . ?
N22 S21 C24 107.49(13) . . ?
C29 S22 C27 90.93(14) . . ?
C21 N21 H20 123(3) . . ?
C21 N21 H21 118(2) . . ?
H20 N21 H21 114(2) . . ?
C27 N22 S21 121.84(19) . . ?
C27 N23 C28 115.6(2) . . ?
C27 N23 H27 122.2 . . ?
C28 N23 H27 122.2 . . ?
N21 C21 C22 120.3(3) . . ?
N21 C21 C26 121.1(3) . . ?
C22 C21 C26 118.6(3) . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.4(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 S21 121.0(2) . . ?
C23 C24 S21 118.8(2) . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.8(3) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
N22 C27 N23 120.0(2) . . ?
N22 C27 S22 130.3(2) . . ?
N23 C27 S22 109.68(19) . . ?
C29 C28 N23 112.7(3) . . ?
C29 C28 H28 123.6 . . ?
N23 C28 H28 123.6 . . ?
C28 C29 S22 111.0(2) . . ?
C28 C29 H29 124.5 . . ?
S22 C29 H29 124.5 . . ?
C33 O30 C30 106.0(3) . . ?
O30 C30 C31 105.7(3) . . ?
O30 C30 H30A 110.6 . . ?
C31 C30 H30A 110.6 . . ?
O30 C30 H30B 110.6 . . ?
C31 C30 H30B 110.6 . . ?
H30A C30 H30B 108.7 . . ?
C30 C31 C32 104.1(3) . . ?
C30 C31 H31A 110.9 . . ?
C32 C31 H31A 110.9 . . ?
C30 C31 H31B 110.9 . . ?
C32 C31 H31B 110.9 . . ?
H31A C31 H31B 109.0 . . ?
C33 C32 C31 104.4(3) . . ?
C33 C32 H32A 110.9 . . ?
C31 C32 H32A 110.9 . . ?
C33 C32 H32B 110.9 . . ?
C31 C32 H32B 110.9 . . ?
H32A C32 H32B 108.9 . . ?
O30 C33 C32 107.1(3) . . ?
O30 C33 H33A 110.3 . . ?
C32 C33 H33A 110.3 . . ?
O30 C33 H33B 110.3 . . ?
C32 C33 H33B 110.3 . . ?
H33A C33 H33B 108.5 . . ?
C43 O40 C40 105.2(3) . . ?
O40 C40 C41 106.8(3) . . ?
O40 C40 H40A 110.4 . . ?
C41 C40 H40A 110.4 . . ?
O40 C40 H40B 110.4 . . ?
C41 C40 H40B 110.4 . . ?
H40A C40 H40B 108.6 . . ?
C40 C41 C42 104.7(3) . . ?
C40 C41 H41A 110.8 . . ?
C42 C41 H41A 110.8 . . ?
C40 C41 H41B 110.8 . . ?
C42 C41 H41B 110.8 . . ?
H41A C41 H41B 108.9 . . ?
C43 C42 C41 103.7(3) . . ?
C43 C42 H42A 111.0 . . ?
C41 C42 H42A 111.0 . . ?
C43 C42 H42B 111.0 . . ?
C41 C42 H42B 111.0 . . ?
H42A C42 H42B 109.0 . . ?
O40 C43 C42 106.0(3) . . ?
O40 C43 H43A 110.5 . . ?
C42 C43 H43A 110.5 . . ?
O40 C43 H43B 110.5 . . ?
C42 C43 H43B 110.5 . . ?
H43A C43 H43B 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 163.8(2) . . . . ?
O12 S11 N12 C17 36.2(3) . . . . ?
C14 S11 N12 C17 -81.3(3) . . . . ?
N11 C11 C12 C13 -176.7(3) . . . . ?
C16 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C12 C13 C14 S11 174.9(2) . . . . ?
O11 S11 C14 C13 24.6(3) . . . . ?
O12 S11 C14 C13 153.0(2) . . . . ?
N12 S11 C14 C13 -87.6(3) . . . . ?
O11 S11 C14 C15 -160.1(2) . . . . ?
O12 S11 C14 C15 -31.6(3) . . . . ?
N12 S11 C14 C15 87.7(3) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
S11 C14 C15 C16 -174.0(2) . . . . ?
C14 C15 C16 C11 -0.9(4) . . . . ?
N11 C11 C16 C15 177.6(3) . . . . ?
C12 C11 C16 C15 -0.3(4) . . . . ?
S11 N12 C17 N13 168.5(2) . . . . ?
S11 N12 C17 S12 -14.3(4) . . . . ?
C18 N13 C17 N12 177.4(3) . . . . ?
C18 N13 C17 S12 -0.4(3) . . . . ?
C19 S12 C17 N12 -177.7(3) . . . . ?
C19 S12 C17 N13 -0.3(2) . . . . ?
C17 N13 C18 C19 1.1(4) . . . . ?
N13 C18 C19 S12 -1.3(4) . . . . ?
C17 S12 C19 C18 0.9(3) . . . . ?
O22 S21 N22 C27 -37.1(3) . . . . ?
O21 S21 N22 C27 -164.7(2) . . . . ?
C24 S21 N22 C27 80.6(3) . . . . ?
N21 C21 C22 C23 -178.6(3) . . . . ?
C26 C21 C22 C23 -0.2(4) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C22 C23 C24 S21 -178.3(2) . . . . ?
O22 S21 C24 C25 17.2(3) . . . . ?
O21 S21 C24 C25 145.5(2) . . . . ?
N22 S21 C24 C25 -102.6(2) . . . . ?
O22 S21 C24 C23 -164.7(2) . . . . ?
O21 S21 C24 C23 -36.3(3) . . . . ?
N22 S21 C24 C23 75.6(2) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
S21 C24 C25 C26 178.4(2) . . . . ?
C24 C25 C26 C21 -0.3(4) . . . . ?
N21 C21 C26 C25 178.7(3) . . . . ?
C22 C21 C26 C25 0.3(4) . . . . ?
S21 N22 C27 N23 177.4(2) . . . . ?
S21 N22 C27 S22 -2.0(4) . . . . ?
C28 N23 C27 N22 179.8(3) . . . . ?
C28 N23 C27 S22 -0.6(4) . . . . ?
C29 S22 C27 N22 -179.2(3) . . . . ?
C29 S22 C27 N23 1.3(2) . . . . ?
C27 N23 C28 C29 -0.7(5) . . . . ?
N23 C28 C29 S22 1.7(4) . . . . ?
C27 S22 C29 C28 -1.8(3) . . . . ?
C33 O30 C30 C31 -36.2(4) . . . . ?
O30 C30 C31 C32 24.5(4) . . . . ?
C30 C31 C32 C33 -4.6(5) . . . . ?
C30 O30 C33 C32 33.4(4) . . . . ?
C31 C32 C33 O30 -17.0(5) . . . . ?
C43 O40 C40 C41 -33.3(4) . . . . ?
O40 C40 C41 C42 15.7(4) . . . . ?
C40 C41 C42 C43 6.7(4) . . . . ?
C40 O40 C43 C42 37.9(3) . . . . ?
C41 C42 C43 O40 -27.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.85(2) 2.13(2) 2.954(3) 163(3) 3_645 yes
N11 H11 O21 0.85(2) 2.26(3) 3.044(3) 155(3) 4_556 yes
N13 H17 N22 0.88 1.98 2.850(3) 167.6 . yes
N21 H20 O22 0.84(2) 2.30(3) 3.036(3) 147(3) 3_656 yes
N21 H21 O11 0.84(2) 2.23(2) 3.067(3) 174(3) 4_466 yes
N23 H27 S11 0.88 2.96 3.767(3) 152.9 . yes
N23 H27 N12 0.88 1.96 2.824(3) 168.0 . yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_37
_database_code_depnum_ccdc_archive 'CCDC 2120798'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 10n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, pyridazine (1:1) solvate'
_chemical_name_common            'Sulfathiazole, pyridazine solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H4 N2'
_chemical_formula_sum            'C13 H13 N5 O2 S2'
_chemical_formula_weight         335.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.390(2)
_cell_length_b                   18.813(4)
_cell_length_c                   9.540(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.54(3)
_cell_angle_gamma                90
_cell_volume                     1469.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    38391
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      30.52

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.377
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38391
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.647
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4455
_reflns_number_gt                3901
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  10n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 2.78      72     81     88.9    10.49    1154.2   61.94  0.0237  0.0236
2.78 - 1.91     158    158    100.0    14.38     613.8   69.67  0.0285  0.0136
1.91 - 1.53     229    229    100.0    14.21     423.5   64.98  0.0330  0.0119
1.53 - 1.33     232    232    100.0    13.69     301.5   60.09  0.0363  0.0130
1.33 - 1.20     232    232    100.0    13.12     221.4   53.15  0.0350  0.0141
1.20 - 1.11     256    256    100.0    12.45     283.1   49.37  0.0335  0.0157
1.11 - 1.04     244    244    100.0    11.51     166.2   40.10  0.0362  0.0182
1.04 - 1.00     184    184    100.0    10.52     107.7   34.40  0.0424  0.0210
1.00 - 0.95     254    254    100.0     9.46      92.4   29.61  0.0439  0.0236
0.95 - 0.91     264    264    100.0     8.30     100.3   24.74  0.0487  0.0275
0.91 - 0.88     208    208    100.0     7.87      88.0   23.53  0.0505  0.0294
0.88 - 0.85     268    268    100.0     6.59      63.5   18.04  0.0631  0.0370
0.85 - 0.83     183    183    100.0     6.50      68.2   17.52  0.0672  0.0400
0.83 - 0.81     212    212    100.0     6.29      61.8   15.23  0.0611  0.0428
0.81 - 0.79     223    223    100.0     6.01      63.1   15.21  0.0715  0.0450
0.79 - 0.77     262    262    100.0     5.57      51.8   12.69  0.0940  0.0561
0.77 - 0.75     274    274    100.0     5.45      46.2   11.65  0.0952  0.0608
0.75 - 0.74     165    165    100.0     5.39      36.3    9.64  0.1147  0.0692
0.74 - 0.72     334    334    100.0     4.88      39.3    9.94  0.1148  0.0725
0.72 - 0.71     173    176     98.3     4.09      44.5    9.81  0.1196  0.0795
0.71 - 0.70     167    186     89.8     3.01      30.3    6.72  0.1716  0.1167
#------------------------------------------------------------------------------
0.80 - 0.70    1491   1513     98.5     4.92      43.3   10.68  0.1051  0.0683
 Inf - 0.70    4594   4625     99.3     8.46     155.5   29.00  0.0377  0.0233
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.7125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4455
_refine_ls_number_parameters     212
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.054

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 1.02580(3) 0.83673(2) 0.61714(3) 0.01772(8) Uani 1 1 d . . . . .
S12 S 1.10351(5) 0.83940(2) 0.29312(4) 0.03277(10) Uani 1 1 d . . . . .
O11 O 1.03847(11) 0.85982(5) 0.76356(9) 0.02371(19) Uani 1 1 d . . . . .
O12 O 1.14592(11) 0.78654(5) 0.58867(10) 0.02394(19) Uani 1 1 d . . . . .
N11 N 0.37918(14) 0.69960(7) 0.44500(14) 0.0291(2) Uani 1 1 d D . . . .
H10 H 0.363(2) 0.6684(10) 0.377(2) 0.047(6) Uiso 1 1 d D . . . .
H11 H 0.294(2) 0.7219(10) 0.458(2) 0.043(5) Uiso 1 1 d D . . . .
N12 N 1.02965(13) 0.90967(5) 0.52813(11) 0.0203(2) Uani 1 1 d . . . . .
N13 N 1.06172(16) 0.97130(6) 0.32635(12) 0.0263(2) Uani 1 1 d . . . . .
H17 H 1.037(2) 1.0112(11) 0.366(2) 0.040(5) Uiso 1 1 d . . . . .
C11 C 0.52643(15) 0.73410(7) 0.47777(13) 0.0212(2) Uani 1 1 d . . . . .
C12 C 0.54639(15) 0.79736(7) 0.55813(14) 0.0233(2) Uani 1 1 d . . . . .
H12 H 0.455034 0.818439 0.585841 0.028 Uiso 1 1 calc R U . . .
C13 C 0.69804(15) 0.82903(7) 0.59699(14) 0.0215(2) Uani 1 1 d . . . . .
H13 H 0.710479 0.871759 0.651366 0.026 Uiso 1 1 calc R U . . .
C14 C 0.83324(14) 0.79861(6) 0.55682(12) 0.0183(2) Uani 1 1 d . . . . .
C15 C 0.81484(15) 0.73720(6) 0.47299(14) 0.0219(2) Uani 1 1 d . . . . .
H15 H 0.905901 0.717303 0.442789 0.026 Uiso 1 1 calc R U . . .
C16 C 0.66252(16) 0.70544(7) 0.43410(14) 0.0235(2) Uani 1 1 d . . . . .
H16 H 0.649944 0.663608 0.376975 0.028 Uiso 1 1 calc R U . . .
C17 C 1.06126(16) 0.90981(6) 0.39824(13) 0.0219(2) Uani 1 1 d . . . . .
C18 C 1.0918(2) 0.96485(8) 0.19004(16) 0.0357(3) Uani 1 1 d . . . . .
H18 H 1.095100 1.004169 0.128251 0.043 Uiso 1 1 calc R U . . .
C19 C 1.1157(3) 0.89746(9) 0.15403(17) 0.0419(4) Uani 1 1 d . . . . .
H19 H 1.136656 0.883255 0.064176 0.050 Uiso 1 1 calc R U . . .
N31 N 0.41211(17) 0.55506(7) 0.28167(16) 0.0378(3) Uani 1 1 d . . . . .
N32 N 0.4863(3) 0.52609(9) 0.1857(2) 0.0622(5) Uani 1 1 d . . . . .
C31 C 0.4793(3) 0.45603(10) 0.1663(3) 0.0637(7) Uani 1 1 d . . . . .
H31 H 0.531777 0.436611 0.096129 0.076 Uiso 1 1 calc R U . . .
C32 C 0.4015(2) 0.40993(8) 0.24065(17) 0.0371(3) Uani 1 1 d . . . . .
H32 H 0.400352 0.360084 0.224500 0.045 Uiso 1 1 calc R U . . .
C33 C 0.3268(3) 0.43944(10) 0.3379(2) 0.0481(4) Uani 1 1 d . . . . .
H33 H 0.269467 0.411165 0.393155 0.058 Uiso 1 1 calc R U . . .
C34 C 0.3367(3) 0.51303(10) 0.3543(2) 0.0512(5) Uani 1 1 d . . . . .
H34 H 0.284827 0.533988 0.423257 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.4445(10) . ?
S11 O12 1.4491(9) . ?
S11 N12 1.6177(11) . ?
S11 C14 1.7470(13) . ?
S12 C19 1.7388(16) . ?
S12 C17 1.7436(13) . ?
N11 C11 1.3702(16) . ?
N11 H10 0.864(16) . ?
N11 H11 0.860(16) . ?
N12 C17 1.3223(16) . ?
N13 C17 1.3452(16) . ?
N13 C18 1.3827(17) . ?
N13 H17 0.88(2) . ?
C11 C16 1.4052(18) . ?
C11 C12 1.4059(18) . ?
C12 C13 1.3808(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3964(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3944(17) . ?
C15 C16 1.3863(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.340(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C34 1.302(2) . ?
N31 N32 1.330(2) . ?
N32 C31 1.331(2) . ?
C31 C32 1.373(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.347(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.394(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.97(6) . . ?
O11 S11 N12 104.30(6) . . ?
O12 S11 N12 111.12(6) . . ?
O11 S11 C14 108.10(6) . . ?
O12 S11 C14 107.57(6) . . ?
N12 S11 C14 107.32(6) . . ?
C19 S12 C17 90.84(7) . . ?
C11 N11 H10 118.9(13) . . ?
C11 N11 H11 118.3(12) . . ?
H10 N11 H11 115.7(14) . . ?
C17 N12 S11 121.64(9) . . ?
C17 N13 C18 115.17(11) . . ?
C17 N13 H17 119.1(13) . . ?
C18 N13 H17 125.6(13) . . ?
N11 C11 C16 120.06(12) . . ?
N11 C11 C12 121.34(12) . . ?
C16 C11 C12 118.57(11) . . ?
C13 C12 C11 120.36(11) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.37(11) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.11(11) . . ?
C15 C14 S11 120.55(9) . . ?
C13 C14 S11 119.31(9) . . ?
C16 C15 C14 119.43(11) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C11 121.09(11) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N12 C17 N13 120.18(11) . . ?
N12 C17 S12 130.14(9) . . ?
N13 C17 S12 109.67(9) . . ?
C19 C18 N13 113.09(13) . . ?
C19 C18 H18 123.5 . . ?
N13 C18 H18 123.5 . . ?
C18 C19 S12 111.21(11) . . ?
C18 C19 H19 124.4 . . ?
S12 C19 H19 124.4 . . ?
C34 N31 N32 118.10(14) . . ?
N31 N32 C31 119.29(16) . . ?
N32 C31 C32 124.40(18) . . ?
N32 C31 H31 117.8 . . ?
C32 C31 H31 117.8 . . ?
C33 C32 C31 116.14(16) . . ?
C33 C32 H32 121.9 . . ?
C31 C32 H32 121.9 . . ?
C32 C33 C34 117.48(16) . . ?
C32 C33 H33 121.3 . . ?
C34 C33 H33 121.3 . . ?
N31 C34 C33 124.58(17) . . ?
N31 C34 H34 117.7 . . ?
C33 C34 H34 117.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 162.87(10) . . . . ?
O12 S11 N12 C17 34.75(12) . . . . ?
C14 S11 N12 C17 -82.60(12) . . . . ?
N11 C11 C12 C13 176.25(12) . . . . ?
C16 C11 C12 C13 -2.15(19) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 2.12(19) . . . . ?
C12 C13 C14 S11 -175.96(10) . . . . ?
O11 S11 C14 C15 -139.40(10) . . . . ?
O12 S11 C14 C15 -11.02(12) . . . . ?
N12 S11 C14 C15 108.63(11) . . . . ?
O11 S11 C14 C13 38.68(11) . . . . ?
O12 S11 C14 C13 167.06(10) . . . . ?
N12 S11 C14 C13 -73.29(11) . . . . ?
C13 C14 C15 C16 -2.13(19) . . . . ?
S11 C14 C15 C16 175.93(10) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
N11 C11 C16 C15 -176.28(12) . . . . ?
C12 C11 C16 C15 2.13(19) . . . . ?
S11 N12 C17 N13 179.24(10) . . . . ?
S11 N12 C17 S12 0.19(18) . . . . ?
C18 N13 C17 N12 -178.27(13) . . . . ?
C18 N13 C17 S12 0.96(16) . . . . ?
C19 S12 C17 N12 178.00(15) . . . . ?
C19 S12 C17 N13 -1.13(12) . . . . ?
C17 N13 C18 C19 -0.2(2) . . . . ?
N13 C18 C19 S12 -0.7(2) . . . . ?
C17 S12 C19 C18 1.07(16) . . . . ?
C34 N31 N32 C31 0.8(3) . . . . ?
N31 N32 C31 C32 -0.9(4) . . . . ?
N32 C31 C32 C33 0.8(4) . . . . ?
C31 C32 C33 C34 -0.5(3) . . . . ?
N32 N31 C34 C33 -0.6(3) . . . . ?
C32 C33 C34 N31 0.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 N31 0.864(16) 2.390(17) 3.1757(19) 151.6(18) . yes
N11 H11 O12 0.860(16) 2.293(16) 3.0902(17) 154.2(16) 1_455 yes
N13 H17 N12 0.88(2) 1.95(2) 2.8270(16) 171.8(18) 3_776 yes
N13 H17 O11 0.88(2) 2.73(2) 3.3502(16) 128.0(16) 3_776 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_38
_database_code_depnum_ccdc_archive 'CCDC 2120804'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 11n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, 4-methylthiazole (1:1) solvate'
_chemical_name_common            'Sulfathiazole, 4-methylthiazole solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H5 N S'
_chemical_formula_sum            'C13 H14 N4 O2 S3'
_chemical_formula_weight         354.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.167(2)
_cell_length_b                   12.443(2)
_cell_length_c                   15.632(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.88(3)
_cell_angle_gamma                90
_cell_volume                     1577.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10089
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      25.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.481
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10089
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.528
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.046
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2770
_reflns_number_gt                1792
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  11n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.64      44     45     97.8     3.38      74.7   21.48  0.0440  0.0329
3.64 - 2.36     104    104    100.0     3.73      49.5   19.82  0.0388  0.0314
2.36 - 1.84     147    147    100.0     3.82      28.6   17.66  0.0418  0.0384
1.84 - 1.60     149    149    100.0     3.83      20.2   15.36  0.0528  0.0426
1.60 - 1.45     154    154    100.0     4.03      16.6   14.13  0.0548  0.0475
1.45 - 1.34     148    148    100.0     3.81      11.5   10.12  0.0838  0.0648
1.34 - 1.27     132    132    100.0     3.89      13.3   11.61  0.0766  0.0625
1.27 - 1.20     151    152     99.3     3.86      11.9    9.87  0.0798  0.0707
1.20 - 1.14     165    165    100.0     3.88      12.4    8.71  0.0831  0.0736
1.14 - 1.10     137    137    100.0     3.77       8.1    7.43  0.1116  0.1003
1.10 - 1.06     146    146    100.0     3.80       6.9    6.17  0.1198  0.1177
1.06 - 1.03     130    130    100.0     3.90       6.4    5.97  0.1435  0.1240
1.03 - 1.00     149    149    100.0     3.87       5.2    5.05  0.1691  0.1492
1.00 - 0.97     164    164    100.0     3.82       5.0    5.10  0.1773  0.1638
0.97 - 0.95     124    124    100.0     3.64       3.1    3.27  0.2846  0.2582
0.95 - 0.92     193    194     99.5     3.51       3.3    3.22  0.2603  0.2611
0.92 - 0.90     160    161     99.4     3.26       3.5    3.27  0.2715  0.2788
0.90 - 0.88     158    159     99.4     2.99       2.5    2.23  0.3378  0.3987
0.88 - 0.87      85     86     98.8     2.94       2.7    2.34  0.4007  0.4069
0.87 - 0.85     192    195     98.5     2.46       2.4    1.79  0.4083  0.5254
0.85 - 0.84      93    101     92.1     2.17       2.0    1.42  0.4456  0.6634
#------------------------------------------------------------------------------
0.94 - 0.84     818    833     98.2     2.89       2.8    2.39  0.3256  0.3934
 Inf - 0.84    2925   2942     99.4     3.56      11.3    7.82  0.0880  0.0853
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2770
_refine_ls_number_parameters     213
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.072

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.51172(9) 0.37901(6) 0.19059(5) 0.0246(2) Uani 1 1 d . . . . .
S12 S 0.35609(11) 0.21244(7) 0.03851(6) 0.0354(3) Uani 1 1 d . . . . .
O11 O 0.6553(2) 0.43448(18) 0.23005(14) 0.0343(6) Uani 1 1 d . . . . .
O12 O 0.5028(3) 0.26385(17) 0.20205(14) 0.0316(6) Uani 1 1 d . . . . .
N11 N -0.0702(4) 0.5841(3) 0.3123(2) 0.0348(8) Uani 1 1 d D . . . .
H10 H -0.154(4) 0.542(3) 0.317(2) 0.062(14) Uiso 1 1 d D . . . .
H11 H -0.055(3) 0.628(2) 0.3555(18) 0.035(10) Uiso 1 1 d D . . . .
N12 N 0.4955(3) 0.4101(2) 0.09011(16) 0.0234(6) Uani 1 1 d . . . . .
N13 N 0.3791(4) 0.3800(3) -0.05010(19) 0.0320(7) Uani 1 1 d . . . . .
H17 H 0.404(4) 0.438(3) -0.060(2) 0.037(12) Uiso 1 1 d . . . . .
C11 C 0.0640(4) 0.5333(3) 0.2866(2) 0.0240(7) Uani 1 1 d . . . . .
C12 C 0.2175(3) 0.5861(3) 0.2946(2) 0.0255(8) Uani 1 1 d . . . . .
H12 H 0.227985 0.655580 0.319781 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3527(4) 0.5376(2) 0.26616(19) 0.0226(7) Uani 1 1 d . . . . .
H13 H 0.455419 0.574270 0.271601 0.027 Uiso 1 1 calc R U . . .
C14 C 0.3406(3) 0.4364(2) 0.22987(18) 0.0191(7) Uani 1 1 d . . . . .
C15 C 0.1909(3) 0.3826(3) 0.22306(19) 0.0231(7) Uani 1 1 d . . . . .
H15 H 0.182626 0.312369 0.199113 0.028 Uiso 1 1 calc R U . . .
C16 C 0.0541(3) 0.4298(2) 0.2506(2) 0.0237(8) Uani 1 1 d . . . . .
H16 H -0.047777 0.392137 0.245178 0.028 Uiso 1 1 calc R U . . .
C17 C 0.4186(4) 0.3461(3) 0.0310(2) 0.0255(8) Uani 1 1 d . . . . .
C18 C 0.3020(5) 0.3063(3) -0.1071(2) 0.0419(10) Uani 1 1 d . . . . .
H18 H 0.268476 0.320875 -0.166286 0.050 Uiso 1 1 calc R U . . .
C19 C 0.2796(5) 0.2111(3) -0.0692(2) 0.0435(10) Uani 1 1 d . . . . .
H19 H 0.227978 0.150719 -0.098154 0.052 Uiso 1 1 calc R U . . .
S31 S 0.15674(12) 0.88912(8) 0.56785(6) 0.0439(3) Uani 1 1 d . . . . .
N31 N 0.0976(3) 0.7357(2) 0.46048(19) 0.0379(8) Uani 1 1 d . . . . .
C31 C 0.0700(4) 0.8378(3) 0.4731(2) 0.0447(10) Uani 1 1 d . . . . .
H31 H 0.005189 0.880462 0.431449 0.054 Uiso 1 1 calc R U . . .
C32 C 0.1977(4) 0.6948(3) 0.5299(2) 0.0314(8) Uani 1 1 d . . . . .
C33 C 0.2376(4) 0.7654(3) 0.5934(2) 0.0372(9) Uani 1 1 d . . . . .
H33 H 0.302810 0.748711 0.646198 0.045 Uiso 1 1 calc R U . . .
C34 C 0.2493(5) 0.5793(3) 0.5287(3) 0.0477(10) Uani 1 1 d . . . . .
H34A H 0.323832 0.563214 0.581046 0.071 Uiso 1 1 calc R U . . .
H34B H 0.306302 0.566104 0.478004 0.071 Uiso 1 1 calc R U . . .
H34C H 0.151659 0.533185 0.526293 0.071 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.435(2) . ?
S11 O12 1.447(2) . ?
S11 N12 1.608(3) . ?
S11 C14 1.745(3) . ?
S12 C19 1.724(4) . ?
S12 C17 1.748(3) . ?
N11 C11 1.366(4) . ?
N11 H10 0.87(2) . ?
N11 H11 0.87(2) . ?
N12 C17 1.320(4) . ?
N13 C17 1.339(4) . ?
N13 C18 1.378(4) . ?
N13 H17 0.77(3) . ?
C11 C16 1.404(4) . ?
C11 C12 1.407(4) . ?
C12 C13 1.378(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C15 C16 1.376(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.347(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S31 C31 1.689(4) . ?
S31 C33 1.703(4) . ?
N31 C31 1.310(5) . ?
N31 C32 1.376(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.336(5) . ?
C32 C34 1.498(5) . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.30(14) . . ?
O11 S11 N12 105.78(14) . . ?
O12 S11 N12 111.09(13) . . ?
O11 S11 C14 107.43(14) . . ?
O12 S11 C14 107.88(13) . . ?
N12 S11 C14 105.63(13) . . ?
C19 S12 C17 91.03(17) . . ?
C11 N11 H10 114(2) . . ?
C11 N11 H11 118(2) . . ?
H10 N11 H11 111.0(16) . . ?
C17 N12 S11 121.0(2) . . ?
C17 N13 C18 116.3(3) . . ?
C17 N13 H17 117(3) . . ?
C18 N13 H17 127(3) . . ?
N11 C11 C16 122.2(3) . . ?
N11 C11 C12 119.7(3) . . ?
C16 C11 C12 118.1(3) . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 S11 119.8(2) . . ?
C15 C14 S11 120.8(2) . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N12 C17 N13 120.9(3) . . ?
N12 C17 S12 130.2(3) . . ?
N13 C17 S12 108.9(3) . . ?
C19 C18 N13 112.1(3) . . ?
C19 C18 H18 124.0 . . ?
N13 C18 H18 124.0 . . ?
C18 C19 S12 111.7(3) . . ?
C18 C19 H19 124.2 . . ?
S12 C19 H19 124.2 . . ?
C31 S31 C33 88.54(18) . . ?
C31 N31 C32 109.7(3) . . ?
N31 C31 S31 115.9(3) . . ?
N31 C31 H31 122.0 . . ?
S31 C31 H31 122.0 . . ?
C33 C32 N31 114.3(3) . . ?
C33 C32 C34 126.6(3) . . ?
N31 C32 C34 119.1(3) . . ?
C32 C33 S31 111.5(3) . . ?
C32 C33 H33 124.2 . . ?
S31 C33 H33 124.2 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 154.9(2) . . . . ?
O12 S11 N12 C17 25.3(3) . . . . ?
C14 S11 N12 C17 -91.4(3) . . . . ?
N11 C11 C12 C13 -177.7(3) . . . . ?
C16 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C12 C13 C14 S11 177.5(2) . . . . ?
O11 S11 C14 C13 19.7(3) . . . . ?
O12 S11 C14 C13 148.3(2) . . . . ?
N12 S11 C14 C13 -92.9(3) . . . . ?
O11 S11 C14 C15 -162.0(2) . . . . ?
O12 S11 C14 C15 -33.4(3) . . . . ?
N12 S11 C14 C15 85.5(3) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
S11 C14 C15 C16 -177.1(2) . . . . ?
C14 C15 C16 C11 -0.4(4) . . . . ?
N11 C11 C16 C15 178.0(3) . . . . ?
C12 C11 C16 C15 -0.8(5) . . . . ?
S11 N12 C17 N13 167.9(2) . . . . ?
S11 N12 C17 S12 -13.6(4) . . . . ?
C18 N13 C17 N12 178.8(3) . . . . ?
C18 N13 C17 S12 0.0(4) . . . . ?
C19 S12 C17 N12 -178.8(3) . . . . ?
C19 S12 C17 N13 -0.2(3) . . . . ?
C17 N13 C18 C19 0.3(5) . . . . ?
N13 C18 C19 S12 -0.4(4) . . . . ?
C17 S12 C19 C18 0.3(3) . . . . ?
C32 N31 C31 S31 -1.3(4) . . . . ?
C33 S31 C31 N31 0.2(3) . . . . ?
C31 N31 C32 C33 2.1(5) . . . . ?
C31 N31 C32 C34 -178.5(3) . . . . ?
N31 C32 C33 S31 -2.0(4) . . . . ?
C34 C32 C33 S31 178.7(3) . . . . ?
C31 S31 C33 C32 1.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.87(2) 2.36(3) 3.075(4) 140(3) 1_455 yes
N11 H11 N31 0.87(2) 2.35(2) 3.168(4) 157(2) . yes
N13 H17 N12 0.77(3) 2.13(4) 2.901(4) 173(3) 3_665 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 2120801'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 6o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_5                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 0.98 angstrom. Data were integrated to 0.84
angstrom resolution, but are truncated at 0.95 angstrom resolution for the
refinement.
;
_vrf_PLAT029_5                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.929 Why?  
RESPONSE: The missing 7% of data are distributed evenly through reciprocal
space and there is no adverse impact on the refinement.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, acetone (1:1) solvate'
_chemical_name_common            'Sulfathiazole, acetone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C3 H6 O'
_chemical_formula_sum            'C12 H15 N3 O3 S2'
_chemical_formula_weight         313.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.322(1)
_cell_length_b                   16.020(1)
_cell_length_c                   11.352(1)
_cell_angle_alpha                90
_cell_angle_beta                 100.29(1)
_cell_angle_gamma                90
_cell_volume                     1489.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4319
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      21.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.367
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4319
_diffrn_reflns_av_unetI/netI     0.1563
_diffrn_reflns_av_R_equivalents  0.1333
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.223
_diffrn_reflns_theta_max         21.964
_diffrn_reflns_theta_full        21.964
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.929
_reflns_number_total             1687
_reflns_number_gt                1067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  6o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.67      33     37     89.2     2.78      79.9   44.45  0.2154  0.0171
3.67 - 2.49      74     81     91.4     2.69      43.6   21.56  0.1587  0.0285
2.49 - 1.97     107    111     96.4     2.77      20.2   12.44  0.1111  0.0653
1.97 - 1.70     110    118     93.2     2.60      18.8    9.80  0.1155  0.0681
1.70 - 1.55     104    112     92.9     2.61      10.6    7.17  0.0972  0.1173
1.55 - 1.42     118    124     95.2     2.64      11.7    6.18  0.1113  0.1154
1.42 - 1.34     107    118     90.7     2.52       9.5    5.89  0.0920  0.1315
1.34 - 1.27     108    112     96.4     2.65       9.0    5.36  0.1048  0.1466
1.27 - 1.21     107    120     89.2     2.42       8.7    5.18  0.1093  0.1582
1.21 - 1.17      93     97     95.9     2.38       7.5    4.08  0.1012  0.1973
1.17 - 1.13     118    127     92.9     2.38       8.7    4.41  0.1009  0.1802
1.13 - 1.09     108    124     87.1     2.16       7.0    3.78  0.1027  0.2138
1.09 - 1.06      94    103     91.3     2.04       5.0    2.88  0.1299  0.3067
1.06 - 1.02     156    170     91.8     1.91       4.6    2.44  0.1074  0.3550
1.02 - 1.00      76     94     80.9     1.81       4.9    2.66  0.1341  0.3241
1.00 - 0.97     132    152     86.8     1.71       3.7    2.04  0.1255  0.4449
0.97 - 0.95      86    107     80.4     1.56       3.2    1.71  0.1073  0.5236
0.95 - 0.93      99    127     78.0     1.44       3.1    1.57  0.1428  0.5482
0.93 - 0.91     105    136     77.2     1.35       3.3    1.60  0.1265  0.5341
0.91 - 0.88     123    231     53.2     0.82       2.8    1.40  0.1734  0.6369
0.88 - 0.84      87    346     25.1     0.31       2.8    1.15  0.1637  0.7015
#--------------------------------------------------------------------------------
0.94 - 0.84     368    779     47.2     0.74       3.1    1.45  0.1477  0.5947
 Inf - 0.84    2145   2747     78.1     1.83      10.0    5.54  0.1337  0.1504
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1687
_refine_ls_number_parameters     190
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_restrained_S_all      0.879
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.080

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.44200(14) 0.67901(9) 0.12624(14) 0.0220(4) Uani 1 1 d . . . . .
S12 S 0.38442(17) 0.52626(10) 0.31085(15) 0.0386(5) Uani 1 1 d . . . . .
O11 O 0.5573(3) 0.7198(2) 0.0648(3) 0.0294(10) Uani 1 1 d . . . . .
O12 O 0.4640(3) 0.6873(2) 0.2556(3) 0.0269(10) Uani 1 1 d . . . . .
N11 N -0.2144(5) 0.8132(3) -0.0652(5) 0.0339(14) Uani 1 1 d D . . . .
H10 H -0.300(5) 0.789(3) -0.049(5) 0.051 Uiso 1 1 d D U . . .
H11 H -0.239(5) 0.848(3) -0.123(5) 0.051 Uiso 1 1 d D U . . .
N12 N 0.4440(4) 0.5823(3) 0.0895(4) 0.0216(11) Uani 1 1 d . . . . .
N13 N 0.4222(5) 0.4419(3) 0.1306(4) 0.0302(12) Uani 1 1 d . . . . .
H17 H 0.439488 0.426766 0.059377 0.045 Uiso 1 1 calc R U . . .
C11 C -0.0633(5) 0.7781(3) -0.0234(5) 0.0225(14) Uani 1 1 d . . . . .
C12 C 0.0718(6) 0.8023(3) -0.0754(5) 0.0339(17) Uani 1 1 d . . . . .
H12 H 0.057180 0.839957 -0.141080 0.041 Uiso 1 1 calc R U . . .
C13 C 0.2251(6) 0.7710(3) -0.0305(5) 0.0278(15) Uani 1 1 d . . . . .
H13 H 0.315564 0.787059 -0.065871 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2478(5) 0.7172(3) 0.0642(5) 0.0191(13) Uani 1 1 d . . . . .
C15 C 0.1142(5) 0.6915(3) 0.1147(5) 0.0245(15) Uani 1 1 d . . . . .
H15 H 0.129533 0.653407 0.179824 0.029 Uiso 1 1 calc R U . . .
C16 C -0.0385(5) 0.7215(3) 0.0698(5) 0.0271(15) Uani 1 1 d . . . . .
H16 H -0.128981 0.703029 0.103379 0.033 Uiso 1 1 calc R U . . .
C17 C 0.4210(5) 0.5222(4) 0.1629(5) 0.0235(14) Uani 1 1 d . . . . .
C18 C 0.3948(7) 0.3840(4) 0.2148(6) 0.0447(17) Uani 1 1 d . . . . .
H18 H 0.393006 0.325372 0.201631 0.054 Uiso 1 1 calc R U . . .
C19 C 0.3714(7) 0.4190(4) 0.3157(6) 0.0459(17) Uani 1 1 d . . . . .
H19 H 0.349830 0.388601 0.383084 0.055 Uiso 1 1 calc R U . . .
O30 O 0.8293(5) 0.5630(3) 0.2327(4) 0.0582(14) Uani 1 1 d . . . . .
C31 C 0.8638(7) 0.4926(5) 0.2415(8) 0.059(2) Uani 1 1 d . . . . .
C32 C 0.9235(10) 0.4503(7) 0.1473(10) 0.162(6) Uani 1 1 d . U . . .
H32A H 0.854182 0.401858 0.121626 0.243 Uiso 1 1 calc R U . . .
H32B H 1.035797 0.431662 0.176133 0.243 Uiso 1 1 calc R U . . .
H32C H 0.921538 0.488410 0.079511 0.243 Uiso 1 1 calc R U . . .
C33 C 0.8451(13) 0.4445(8) 0.3427(13) 0.209(7) Uani 1 1 d . U . . .
H33A H 0.951197 0.438503 0.395592 0.313 Uiso 1 1 calc R U . . .
H33B H 0.802637 0.389182 0.316584 0.313 Uiso 1 1 calc R U . . .
H33C H 0.768466 0.472468 0.385946 0.313 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.440(4) . ?
S11 O12 1.453(4) . ?
S11 N12 1.606(4) . ?
S11 C14 1.754(5) . ?
S12 C19 1.724(6) . ?
S12 C17 1.761(6) . ?
N11 C11 1.382(6) . ?
N11 H10 0.86(3) . ?
N11 H11 0.86(3) . ?
N12 C17 1.309(7) . ?
N13 C17 1.339(7) . ?
N13 C18 1.380(7) . ?
N13 H17 0.8800 . ?
C11 C16 1.381(7) . ?
C11 C12 1.414(7) . ?
C12 C13 1.380(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.364(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.401(7) . ?
C15 C16 1.369(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.321(9) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C31 1.163(8) . ?
C31 C33 1.415(12) . ?
C31 C32 1.428(12) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.2(2) . . ?
O11 S11 N12 105.9(2) . . ?
O12 S11 N12 110.2(2) . . ?
O11 S11 C14 107.0(2) . . ?
O12 S11 C14 108.3(2) . . ?
N12 S11 C14 106.5(2) . . ?
C19 S12 C17 90.9(3) . . ?
C11 N11 H10 119(3) . . ?
C11 N11 H11 127(3) . . ?
H10 N11 H11 111.3(18) . . ?
C17 N12 S11 122.3(4) . . ?
C17 N13 C18 116.5(5) . . ?
C17 N13 H17 121.7 . . ?
C18 N13 H17 121.7 . . ?
C16 C11 N11 122.2(5) . . ?
C16 C11 C12 118.6(4) . . ?
N11 C11 C12 119.2(5) . . ?
C13 C12 C11 119.8(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.6(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 S11 121.7(4) . . ?
C15 C14 S11 118.3(4) . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.2(5) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N12 C17 N13 121.6(5) . . ?
N12 C17 S12 130.5(5) . . ?
N13 C17 S12 107.9(4) . . ?
C19 C18 N13 112.5(6) . . ?
C19 C18 H18 123.7 . . ?
N13 C18 H18 123.7 . . ?
C18 C19 S12 112.1(5) . . ?
C18 C19 H19 124.0 . . ?
S12 C19 H19 124.0 . . ?
O30 C31 C33 122.5(10) . . ?
O30 C31 C32 120.6(9) . . ?
C33 C31 C32 116.9(10) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 147.0(4) . . . . ?
O12 S11 N12 C17 18.0(4) . . . . ?
C14 S11 N12 C17 -99.3(4) . . . . ?
C16 C11 C12 C13 -1.7(8) . . . . ?
N11 C11 C12 C13 176.7(5) . . . . ?
C11 C12 C13 C14 -0.4(8) . . . . ?
C12 C13 C14 C15 1.7(8) . . . . ?
C12 C13 C14 S11 -177.9(4) . . . . ?
O11 S11 C14 C13 4.2(5) . . . . ?
O12 S11 C14 C13 132.7(5) . . . . ?
N12 S11 C14 C13 -108.7(5) . . . . ?
O11 S11 C14 C15 -175.5(4) . . . . ?
O12 S11 C14 C15 -46.9(5) . . . . ?
N12 S11 C14 C15 71.6(5) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
S11 C14 C15 C16 178.7(4) . . . . ?
C14 C15 C16 C11 -1.2(8) . . . . ?
N11 C11 C16 C15 -175.9(5) . . . . ?
C12 C11 C16 C15 2.5(8) . . . . ?
S11 N12 C17 N13 179.6(3) . . . . ?
S11 N12 C17 S12 -0.1(6) . . . . ?
C18 N13 C17 N12 -179.3(4) . . . . ?
C18 N13 C17 S12 0.5(5) . . . . ?
C19 S12 C17 N12 179.1(5) . . . . ?
C19 S12 C17 N13 -0.7(4) . . . . ?
C17 N13 C18 C19 0.1(7) . . . . ?
N13 C18 C19 S12 -0.6(7) . . . . ?
C17 S12 C19 C18 0.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.86(3) 2.20(4) 3.004(6) 155(4) 1_455 yes
N11 H11 O30 0.86(3) 2.32(4) 3.103(7) 152(4) 4_475 yes
N13 H17 S11 0.88 3.00 3.835(5) 158.0 3_665 yes
N13 H17 N12 0.88 2.10 2.937(7) 159.1 3_665 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 2120806'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 3o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_2                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.08 angstrom. Data were integrated to 0.84
angstrom resolution, but this gives well below 50% observed at the 2sigma(I)
level. For the refinement, the data are truncated at 0.95 angstrom resolution.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, cyclohexanol (1:1) solvate'
_chemical_name_common            'Sulfathiazole, cyclohexanol solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C6 H12 O'
_chemical_formula_sum            'C15 H21 N3 O3 S2'
_chemical_formula_weight         355.47
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.541(2)
_cell_length_b                   12.401(2)
_cell_length_c                   8.836(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.96(3)
_cell_angle_gamma                90
_cell_volume                     912.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3242
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      21.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.308
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3242
_diffrn_reflns_av_unetI/netI     0.1989
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.365
_diffrn_reflns_theta_max         21.957
_diffrn_reflns_theta_full        21.957
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             1960
_reflns_number_gt                1037
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.982

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  3o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.91      22     23     95.7     3.30     874.4   57.37  0.1886  0.0184
3.91 - 2.51      49     49    100.0     3.33     393.2   25.64  0.0511  0.0349
2.51 - 1.98      71     71    100.0     3.13     159.1   12.90  0.0467  0.0695
1.98 - 1.71      71     71    100.0     3.23     161.9   11.71  0.0436  0.0734
1.71 - 1.54      73     73    100.0     3.14      79.7    6.78  0.0673  0.1279
1.54 - 1.43      71     72     98.6     3.10      63.6    5.91  0.0734  0.1562
1.43 - 1.34      75     76     98.7     3.21      73.7    5.97  0.0675  0.1468
1.34 - 1.27      66     67     98.5     3.18      60.0    5.28  0.0920  0.1713
1.27 - 1.21      80     81     98.8     2.89      47.1    3.83  0.0904  0.2419
1.21 - 1.16      78     79     98.7     2.85      40.4    3.33  0.0914  0.2718
1.16 - 1.13      53     54     98.1     3.06      51.7    3.93  0.0981  0.2275
1.13 - 1.08      86     89     96.6     2.48      33.8    2.63  0.1200  0.3773
1.08 - 1.05      75     78     96.2     2.35      18.8    1.63  0.1674  0.6264
1.05 - 1.03      51     53     96.2     2.43      23.0    1.79  0.1592  0.5264
1.03 - 1.00      82     89     92.1     2.17      18.2    1.47  0.1838  0.6914
1.00 - 0.97      78     84     92.9     2.07      13.8    1.13  0.2538  0.8923
0.97 - 0.95      63     72     87.5     1.85      13.2    1.03  0.2732  0.9608
0.95 - 0.93      70     80     87.5     1.90      12.6    1.05  0.2692  0.9593
0.93 - 0.91      74     83     89.2     1.96      12.8    1.06  0.2604  0.9381
0.91 - 0.89      60     86     69.8     1.21      10.0    0.81  0.2562  1.2486
0.89 - 0.86      69    157     43.9     0.62       7.1    0.57  0.3068  1.7685
0.86 - 0.84       9     87     10.3     0.13       5.3    0.38  0.2041  2.3767
#--------------------------------------------------------------------------------
0.94 - 0.84     246    451     54.5     0.99      10.3    0.84  0.2572  1.1930
 Inf - 0.84    1426   1674     85.2     2.26      72.0    5.40  0.0997  0.1641
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
Refined as a 2-component inversion twin (explicit refinement of Flack
parameter).

The H atoms of the NH2 group could not readily be refined, so they were
placed in-plane and allowed to ride. This is an approximation.

The displacement parameters of the C atoms in cyclohexanol were
restrained to resemble isotropic behaviour.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0080P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.6(2)
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_number_reflns         1960
_refine_ls_number_parameters     210
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   0.683
_refine_ls_restrained_S_all      0.728
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.049

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.8428(3) 0.2515(2) 0.5888(3) 0.0502(8) Uani 1 1 d . . . . .
S12 S 0.9071(4) 0.2385(2) 0.9641(3) 0.0580(9) Uani 1 1 d . . . . .
O11 O 0.8866(8) 0.2602(6) 0.4417(8) 0.062(2) Uani 1 1 d . . . . .
O12 O 0.8439(9) 0.3505(4) 0.6744(8) 0.055(2) Uani 1 1 d . . . . .
N11 N 0.1882(11) 0.0712(6) 0.4830(10) 0.061(3) Uani 1 1 d . . . . .
H10 H 0.115988 0.102528 0.525364 0.091 Uiso 1 1 calc R U . . .
H11 H 0.162992 0.012693 0.426468 0.091 Uiso 1 1 calc R U . . .
N12 N 0.9616(10) 0.1623(6) 0.6837(11) 0.046(2) Uani 1 1 d . . . . .
N13 N 1.0508(10) 0.0727(6) 0.9155(10) 0.049(2) Uani 1 1 d . . . . .
H17 H 1.092648 0.020220 0.870262 0.074 Uiso 1 1 calc R U . . .
C11 C 0.3352(15) 0.1123(9) 0.5045(13) 0.049(3) Uani 1 1 d . . . . .
C12 C 0.4568(16) 0.0654(8) 0.4448(12) 0.062(4) Uani 1 1 d . . . . .
H12 H 0.431486 0.002830 0.382041 0.074 Uiso 1 1 calc R U . . .
C13 C 0.6150(15) 0.1053(8) 0.4719(12) 0.056(3) Uani 1 1 d . . . . .
H13 H 0.695206 0.068604 0.432646 0.068 Uiso 1 1 calc R U . . .
C14 C 0.6507(13) 0.1996(8) 0.5574(14) 0.049(3) Uani 1 1 d . . . . .
C15 C 0.5357(13) 0.2471(9) 0.6204(11) 0.053(3) Uani 1 1 d . . . . .
H15 H 0.561409 0.309589 0.683264 0.064 Uiso 1 1 calc R U . . .
C16 C 0.3802(16) 0.2044(8) 0.5928(14) 0.061(4) Uani 1 1 d . . . . .
H16 H 0.302083 0.239986 0.636395 0.073 Uiso 1 1 calc R U . . .
C17 C 0.9759(12) 0.1554(8) 0.8350(14) 0.043(3) Uani 1 1 d . . . . .
C18 C 1.0600(14) 0.0730(9) 1.0727(13) 0.060(4) Uani 1 1 d . . . . .
H18 H 1.112002 0.018047 1.140582 0.071 Uiso 1 1 calc R U . . .
C19 C 0.9883(15) 0.1586(10) 1.1211(14) 0.067(4) Uani 1 1 d . . . . .
H19 H 0.983182 0.172726 1.225575 0.081 Uiso 1 1 calc R U . . .
O30 O 0.7823(9) 0.4035(6) 0.1915(9) 0.062(2) Uani 1 1 d . . . . .
H30 H 0.819599 0.368198 0.272776 0.093 Uiso 1 1 calc R U . . .
C30 C 0.6097(16) 0.4091(13) 0.1668(17) 0.090(4) Uani 1 1 d . . . . .
H30A H 0.580641 0.431982 0.265536 0.109 Uiso 1 1 calc R U . . .
C31 C 0.552(2) 0.4896(12) 0.048(2) 0.132(6) Uani 1 1 d . U . . .
H31A H 0.600740 0.560226 0.084403 0.159 Uiso 1 1 calc R U . . .
H31B H 0.589180 0.470023 -0.047024 0.159 Uiso 1 1 calc R U . . .
C32 C 0.379(2) 0.5003(13) 0.009(2) 0.155(7) Uani 1 1 d . U . . .
H32A H 0.346185 0.552111 -0.077118 0.186 Uiso 1 1 calc R U . . .
H32B H 0.341987 0.528590 0.100349 0.186 Uiso 1 1 calc R U . . .
C33 C 0.3030(18) 0.3945(13) -0.0360(18) 0.129(6) Uani 1 1 d . U . . .
H33A H 0.336742 0.366718 -0.128826 0.154 Uiso 1 1 calc R U . . .
H33B H 0.184562 0.401852 -0.061552 0.154 Uiso 1 1 calc R U . . .
C34 C 0.355(2) 0.3182(15) 0.098(3) 0.172(8) Uani 1 1 d . U . . .
H34A H 0.300815 0.247558 0.073651 0.206 Uiso 1 1 calc R U . . .
H34B H 0.326939 0.347621 0.192392 0.206 Uiso 1 1 calc R U . . .
C35 C 0.5414(19) 0.3050(11) 0.123(2) 0.130(6) Uani 1 1 d . U . . .
H35A H 0.581822 0.251555 0.205557 0.156 Uiso 1 1 calc R U . . .
H35B H 0.569918 0.280318 0.025850 0.156 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.436(6) . ?
S11 O12 1.440(6) . ?
S11 N12 1.605(8) . ?
S11 C14 1.726(11) . ?
S12 C19 1.719(11) . ?
S12 C17 1.734(11) . ?
N11 C11 1.328(12) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.317(12) . ?
N13 C17 1.328(12) . ?
N13 C18 1.374(12) . ?
N13 H17 0.8800 . ?
C11 C16 1.389(14) . ?
C11 C12 1.393(14) . ?
C12 C13 1.408(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(12) . ?
C15 C16 1.400(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.342(14) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C30 1.443(13) . ?
O30 H30 0.8400 . ?
C30 C35 1.434(17) . ?
C30 C31 1.452(17) . ?
C30 H30A 1.0000 . ?
C31 C32 1.45(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.478(19) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.501(19) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.57(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 116.1(5) . . ?
O11 S11 N12 105.2(5) . . ?
O12 S11 N12 112.6(5) . . ?
O11 S11 C14 108.3(5) . . ?
O12 S11 C14 107.2(5) . . ?
N12 S11 C14 107.1(5) . . ?
C19 S12 C17 93.1(6) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 118.6(7) . . ?
C17 N13 C18 116.8(9) . . ?
C17 N13 H17 121.6 . . ?
C18 N13 H17 121.6 . . ?
N11 C11 C16 122.0(11) . . ?
N11 C11 C12 123.2(11) . . ?
C16 C11 C12 114.8(12) . . ?
C11 C12 C13 123.9(10) . . ?
C11 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
C14 C13 C12 118.3(10) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C15 C14 C13 119.6(11) . . ?
C15 C14 S11 121.2(9) . . ?
C13 C14 S11 119.1(9) . . ?
C14 C15 C16 120.5(10) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 122.8(11) . . ?
C11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
N12 C17 N13 121.1(10) . . ?
N12 C17 S12 131.4(8) . . ?
N13 C17 S12 107.5(8) . . ?
C19 C18 N13 113.5(11) . . ?
C19 C18 H18 123.3 . . ?
N13 C18 H18 123.3 . . ?
C18 C19 S12 109.2(9) . . ?
C18 C19 H19 125.4 . . ?
S12 C19 H19 125.4 . . ?
C30 O30 H30 109.5 . . ?
C35 C30 O30 109.7(13) . . ?
C35 C30 C31 111.9(13) . . ?
O30 C30 C31 108.0(12) . . ?
C35 C30 H30A 109.1 . . ?
O30 C30 H30A 109.1 . . ?
C31 C30 H30A 109.1 . . ?
C32 C31 C30 113.1(14) . . ?
C32 C31 H31A 109.0 . . ?
C30 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
C30 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 C33 110.2(15) . . ?
C31 C32 H32A 109.6 . . ?
C33 C32 H32A 109.6 . . ?
C31 C32 H32B 109.6 . . ?
C33 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
C32 C33 C34 108.2(14) . . ?
C32 C33 H33A 110.1 . . ?
C34 C33 H33A 110.1 . . ?
C32 C33 H33B 110.1 . . ?
C34 C33 H33B 110.1 . . ?
H33A C33 H33B 108.4 . . ?
C33 C34 C35 106.7(14) . . ?
C33 C34 H34A 110.4 . . ?
C35 C34 H34A 110.4 . . ?
C33 C34 H34B 110.4 . . ?
C35 C34 H34B 110.4 . . ?
H34A C34 H34B 108.6 . . ?
C30 C35 C34 106.5(13) . . ?
C30 C35 H35A 110.4 . . ?
C34 C35 H35A 110.4 . . ?
C30 C35 H35B 110.4 . . ?
C34 C35 H35B 110.4 . . ?
H35A C35 H35B 108.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 164.1(8) . . . . ?
O12 S11 N12 C17 36.8(10) . . . . ?
C14 S11 N12 C17 -80.8(9) . . . . ?
N11 C11 C12 C13 -177.2(10) . . . . ?
C16 C11 C12 C13 1.1(17) . . . . ?
C11 C12 C13 C14 -3.0(17) . . . . ?
C12 C13 C14 C15 3.9(16) . . . . ?
C12 C13 C14 S11 -178.7(8) . . . . ?
O11 S11 C14 C15 -130.8(9) . . . . ?
O12 S11 C14 C15 -4.9(10) . . . . ?
N12 S11 C14 C15 116.2(9) . . . . ?
O11 S11 C14 C13 51.9(10) . . . . ?
O12 S11 C14 C13 177.8(9) . . . . ?
N12 S11 C14 C13 -61.2(10) . . . . ?
C13 C14 C15 C16 -3.2(16) . . . . ?
S11 C14 C15 C16 179.5(9) . . . . ?
N11 C11 C16 C15 178.1(11) . . . . ?
C12 C11 C16 C15 -0.1(17) . . . . ?
C14 C15 C16 C11 1.2(18) . . . . ?
S11 N12 C17 N13 168.8(8) . . . . ?
S11 N12 C17 S12 -9.5(14) . . . . ?
C18 N13 C17 N12 179.8(10) . . . . ?
C18 N13 C17 S12 -1.5(11) . . . . ?
C19 S12 C17 N12 -179.9(10) . . . . ?
C19 S12 C17 N13 1.5(9) . . . . ?
C17 N13 C18 C19 0.7(15) . . . . ?
N13 C18 C19 S12 0.5(14) . . . . ?
C17 S12 C19 C18 -1.2(10) . . . . ?
C35 C30 C31 C32 57(2) . . . . ?
O30 C30 C31 C32 178.2(15) . . . . ?
C30 C31 C32 C33 -55(2) . . . . ?
C31 C32 C33 C34 59(2) . . . . ?
C32 C33 C34 C35 -64(2) . . . . ?
O30 C30 C35 C34 -179.8(12) . . . . ?
C31 C30 C35 C34 -59.9(18) . . . . ?
C33 C34 C35 C30 63.8(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H11 O12 0.88 2.20 3.055(11) 165.2 2_646 yes
N11 H10 N12 0.88 2.25 3.115(13) 166.6 1_455 yes
N13 H17 O30 0.88 1.95 2.816(11) 168.6 2_746 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_21
_database_code_depnum_ccdc_archive 'CCDC 2120803'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 22o
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, cyclopentanone (1:1) solvate'
_chemical_name_common            'Sulfathiazole, cyclopentanone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C5 H8 O'
_chemical_formula_sum            'C14 H17 N3 O3 S2'
_chemical_formula_weight         339.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.454(1)
_cell_length_b                   20.699(2)
_cell_length_c                   9.487(1)
_cell_angle_alpha                90
_cell_angle_beta                 92.37(1)
_cell_angle_gamma                90
_cell_volume                     1658.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      4.27
_cell_measurement_theta_max      74.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    3.048
_shelx_estimated_absorpt_T_min   0.462
_shelx_estimated_absorpt_T_max   0.462
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            3468
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.272
_diffrn_reflns_theta_max         74.239
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3275
_reflns_number_gt                2557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  22o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.43      51     53     96.2     1.13     694.1  110.16  0.0119  0.0052
3.43 - 2.24     119    119    100.0     1.11     239.6   50.74  0.0048  0.0131
2.24 - 1.76     168    170     98.8     1.08     130.2   35.80  0.0152  0.0189
1.76 - 1.53     175    180     97.2     1.05      73.2   27.37  0.0196  0.0247
1.53 - 1.38     170    177     96.0     1.03      59.5   24.18  0.0206  0.0294
1.38 - 1.28     172    178     96.6     1.02      42.6   21.00  0.0187  0.0329
1.28 - 1.20     170    172     98.8     1.06      38.5   20.84  0.0442  0.0338
1.20 - 1.15     152    157     96.8     1.03      33.5   20.65  0.0247  0.0360
1.15 - 1.09     192    199     96.5     1.02      26.3   17.54  0.0554  0.0404
1.09 - 1.05     151    159     95.0     1.01      20.9   16.84  0.0126  0.0461
1.05 - 1.01     182    194     93.8     0.98      14.2   13.07  0.0369  0.0569
1.01 - 0.98     149    161     92.5     0.97      10.4   11.73  0.0298  0.0675
0.98 - 0.95     169    179     94.4     0.99       7.1   10.06  0.0501  0.0883
0.95 - 0.92     209    220     95.0     1.00       6.8    9.41  0.0568  0.0912
0.92 - 0.90     145    158     91.8     0.96       5.6    8.83  0.1306  0.0982
0.90 - 0.88     163    170     95.9     1.01       4.4    8.05  0.0830  0.1140
0.88 - 0.86     163    172     94.8     0.97       3.7    6.65  0.0718  0.1395
0.86 - 0.84     211    215     98.1     1.03       2.7    6.34  0.0626  0.1582
0.84 - 0.82     224    227     98.7     1.04       2.3    5.43  0.1190  0.1888
0.82 - 0.81     115    115    100.0     1.03       1.3    4.36  0.1471  0.2759
0.81 - 0.80     121    121    100.0     1.03       1.6    4.44  0.2158  0.2348
#------------------------------------------------------------------------------
0.90 - 0.80     997   1020     97.7     1.02       2.8    6.01  0.0913  0.1602
 Inf - 0.80    3371   3496     96.4     1.02      43.4   17.16  0.0141  0.0245
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0889P)²+0.3831P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0038(7)
_refine_ls_number_reflns         3275
_refine_ls_number_parameters     207
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.051

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.55785(7) 0.14472(3) 0.37208(7) 0.0578(2) Uani 1 1 d . . . . .
S12 S 0.65930(15) 0.14247(4) 0.71323(10) 0.1042(4) Uani 1 1 d . . . . .
O11 O 0.5486(2) 0.12089(9) 0.22984(19) 0.0696(5) Uani 1 1 d . . . . .
O12 O 0.6895(2) 0.18541(9) 0.4139(2) 0.0757(6) Uani 1 1 d . . . . .
N11 N -0.0394(3) 0.27351(15) 0.5018(4) 0.0856(9) Uani 1 1 d D . . . .
H10 H -0.052(4) 0.3049(17) 0.559(4) 0.128 Uiso 1 1 d D U . . .
H11 H -0.129(3) 0.262(2) 0.462(4) 0.128 Uiso 1 1 d D U . . .
N12 N 0.5553(3) 0.08038(9) 0.4675(2) 0.0585(5) Uani 1 1 d . . . . .
N13 N 0.5815(3) 0.02633(11) 0.6795(2) 0.0667(6) Uani 1 1 d . . . . .
H17 H 0.550970 -0.009646 0.642088 0.100 Uiso 1 1 calc R U . . .
C11 C 0.0989(3) 0.24467(13) 0.4695(3) 0.0620(6) Uani 1 1 d . . . . .
C12 C 0.1023(3) 0.19602(13) 0.3681(3) 0.0650(7) Uani 1 1 d . . . . .
H12 H 0.008546 0.183223 0.321528 0.078 Uiso 1 1 calc R U . . .
C13 C 0.2415(3) 0.16680(13) 0.3361(3) 0.0613(6) Uani 1 1 d . . . . .
H13 H 0.241390 0.134055 0.268933 0.074 Uiso 1 1 calc R U . . .
C14 C 0.3833(3) 0.18589(11) 0.4036(3) 0.0555(6) Uani 1 1 d . . . . .
C15 C 0.3824(3) 0.23571(12) 0.5025(3) 0.0595(6) Uani 1 1 d . . . . .
H15 H 0.476799 0.249593 0.546260 0.071 Uiso 1 1 calc R U . . .
C16 C 0.2418(3) 0.26427(13) 0.5354(3) 0.0623(6) Uani 1 1 d . . . . .
H16 H 0.241764 0.297082 0.602362 0.075 Uiso 1 1 calc R U . . .
C17 C 0.5933(3) 0.08042(12) 0.6038(3) 0.0618(6) Uani 1 1 d . . . . .
C18 C 0.6212(5) 0.03180(15) 0.8205(3) 0.0898(11) Uani 1 1 d . . . . .
H18 H 0.619790 -0.002596 0.883486 0.108 Uiso 1 1 calc R U . . .
C19 C 0.6615(7) 0.09126(18) 0.8570(4) 0.1186(17) Uani 1 1 d . . . . .
H19 H 0.687969 0.104033 0.949009 0.142 Uiso 1 1 calc R U . . .
O30 O 0.1887(8) 0.0916(3) 1.0048(5) 0.203(2) Uani 1 1 d . . . . .
C30 C 0.1603(6) 0.0761(3) 0.8861(6) 0.1220(16) Uani 1 1 d . . . . .
C31 C 0.1367(9) 0.1169(3) 0.7617(9) 0.185(3) Uani 1 1 d . . . . .
H31A H 0.045900 0.144892 0.772001 0.222 Uiso 1 1 calc R U . . .
H31B H 0.229293 0.143650 0.749027 0.222 Uiso 1 1 calc R U . . .
C32 C 0.1105(13) 0.0742(5) 0.6407(8) 0.226(5) Uani 1 1 d . . . . .
H32A H 0.019008 0.088577 0.584126 0.271 Uiso 1 1 calc R U . . .
H32B H 0.201910 0.074910 0.582300 0.271 Uiso 1 1 calc R U . . .
C33 C 0.0854(9) 0.0118(4) 0.6895(7) 0.174(3) Uani 1 1 d . . . . .
H33A H 0.138737 -0.019072 0.630883 0.209 Uiso 1 1 calc R U . . .
H33B H -0.026925 0.002034 0.684735 0.209 Uiso 1 1 calc R U . . .
C34 C 0.1470(7) 0.0069(3) 0.8350(6) 0.1402(19) Uani 1 1 d . . . . .
H34A H 0.249741 -0.014090 0.839233 0.168 Uiso 1 1 calc R U . . .
H34B H 0.075263 -0.017565 0.891748 0.168 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.436(2) . ?
S11 O12 1.438(2) . ?
S11 N12 1.611(2) . ?
S11 C14 1.741(3) . ?
S12 C19 1.727(4) . ?
S12 C17 1.730(3) . ?
N11 C11 1.359(4) . ?
N11 H10 0.86(3) . ?
N11 H11 0.86(3) . ?
N12 C17 1.320(3) . ?
N13 C17 1.336(3) . ?
N13 C18 1.370(4) . ?
N13 H17 0.8600 . ?
C11 C12 1.394(4) . ?
C11 C16 1.397(4) . ?
C12 C13 1.368(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(3) . ?
C15 C16 1.375(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.320(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O30 C30 1.186(6) . ?
C30 C31 1.459(7) . ?
C30 C34 1.515(8) . ?
C31 C32 1.458(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.391(9) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.459(7) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.17(13) . . ?
O11 S11 N12 104.03(11) . . ?
O12 S11 N12 110.95(12) . . ?
O11 S11 C14 108.41(12) . . ?
O12 S11 C14 108.53(12) . . ?
N12 S11 C14 106.08(12) . . ?
C19 S12 C17 90.64(15) . . ?
C11 N11 H10 127(3) . . ?
C11 N11 H11 122(2) . . ?
H10 N11 H11 110.9(17) . . ?
C17 N12 S11 122.78(17) . . ?
C17 N13 C18 115.8(2) . . ?
C17 N13 H17 122.1 . . ?
C18 N13 H17 122.1 . . ?
N11 C11 C12 121.0(3) . . ?
N11 C11 C16 120.5(3) . . ?
C12 C11 C16 118.5(2) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 S11 120.1(2) . . ?
C15 C14 S11 120.39(19) . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N12 C17 N13 120.4(2) . . ?
N12 C17 S12 130.4(2) . . ?
N13 C17 S12 109.20(19) . . ?
C19 C18 N13 112.6(3) . . ?
C19 C18 H18 123.7 . . ?
N13 C18 H18 123.7 . . ?
C18 C19 S12 111.7(3) . . ?
C18 C19 H19 124.1 . . ?
S12 C19 H19 124.1 . . ?
O30 C30 C31 128.8(6) . . ?
O30 C30 C34 124.8(5) . . ?
C31 C30 C34 106.4(5) . . ?
C32 C31 C30 107.2(6) . . ?
C32 C31 H31A 110.3 . . ?
C30 C31 H31A 110.3 . . ?
C32 C31 H31B 110.3 . . ?
C30 C31 H31B 110.3 . . ?
H31A C31 H31B 108.5 . . ?
C33 C32 C31 108.8(6) . . ?
C33 C32 H32A 109.9 . . ?
C31 C32 H32A 109.9 . . ?
C33 C32 H32B 109.9 . . ?
C31 C32 H32B 109.9 . . ?
H32A C32 H32B 108.3 . . ?
C32 C33 C34 109.0(7) . . ?
C32 C33 H33A 109.9 . . ?
C34 C33 H33A 109.9 . . ?
C32 C33 H33B 109.9 . . ?
C34 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
C33 C34 C30 104.8(5) . . ?
C33 C34 H34A 110.8 . . ?
C30 C34 H34A 110.8 . . ?
C33 C34 H34B 110.8 . . ?
C30 C34 H34B 110.8 . . ?
H34A C34 H34B 108.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 166.1(2) . . . . ?
O12 S11 N12 C17 38.0(3) . . . . ?
C14 S11 N12 C17 -79.7(2) . . . . ?
N11 C11 C12 C13 -179.7(3) . . . . ?
C16 C11 C12 C13 1.7(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C12 C13 C14 S11 175.3(2) . . . . ?
O11 S11 C14 C13 31.4(2) . . . . ?
O12 S11 C14 C13 160.9(2) . . . . ?
N12 S11 C14 C13 -79.8(2) . . . . ?
O11 S11 C14 C15 -152.4(2) . . . . ?
O12 S11 C14 C15 -22.9(3) . . . . ?
N12 S11 C14 C15 96.4(2) . . . . ?
C13 C14 C15 C16 1.8(4) . . . . ?
S11 C14 C15 C16 -174.5(2) . . . . ?
C14 C15 C16 C11 -0.8(4) . . . . ?
N11 C11 C16 C15 -179.5(3) . . . . ?
C12 C11 C16 C15 -0.9(4) . . . . ?
S11 N12 C17 N13 176.6(2) . . . . ?
S11 N12 C17 S12 -2.6(4) . . . . ?
C18 N13 C17 N12 -178.9(3) . . . . ?
C18 N13 C17 S12 0.5(4) . . . . ?
C19 S12 C17 N12 177.7(3) . . . . ?
C19 S12 C17 N13 -1.6(3) . . . . ?
C17 N13 C18 C19 1.4(5) . . . . ?
N13 C18 C19 S12 -2.5(6) . . . . ?
C17 S12 C19 C18 2.4(4) . . . . ?
O30 C30 C31 C32 178.1(8) . . . . ?
C34 C30 C31 C32 0.0(9) . . . . ?
C30 C31 C32 C33 11.9(11) . . . . ?
C31 C32 C33 C34 -19.5(11) . . . . ?
C32 C33 C34 C30 18.8(9) . . . . ?
O30 C30 C34 C33 170.7(7) . . . . ?
C31 C30 C34 C33 -11.0(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.86(3) 2.36(3) 3.143(3) 151(3) 4_566 yes
N11 H11 O12 0.86(3) 2.24(3) 3.019(3) 150(4) 1_455 yes
N13 H17 S11 0.86 2.94 3.757(2) 158.3 3_656 yes
N13 H17 N12 0.86 1.99 2.833(3) 167.1 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_22
_database_code_depnum_ccdc_archive 'CCDC 2120800'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 23o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_22                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.00 angstrom. Data were integrated to 0.84
angstrom resolution, but truncated at 0.95 angstrom resolution for refinement.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1-oxycyclohexan-2-one (1:1) solvate'
_chemical_name_common            'Sulfathiazole, delta-valerolactone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C5 H8 O2'
_chemical_formula_sum            'C14 H17 N3 O4 S2'
_chemical_formula_weight         355.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.583(1)
_cell_length_b                   20.652(2)
_cell_length_c                   9.520(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.66(3)
_cell_angle_gamma                90
_cell_volume                     1684.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5903
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.075
_shelx_estimated_absorpt_T_min   0.459
_shelx_estimated_absorpt_T_max   0.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            2205
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.281
_diffrn_reflns_theta_max         54.234
_diffrn_reflns_theta_full        54.234
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2047
_reflns_number_gt                1157
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  23o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.63      45     46     97.8     1.20     613.0   93.05  0.0302  0.0063
3.63 - 2.37     103    103    100.0     1.14     193.1   39.57  0.0195  0.0169
2.37 - 1.86     147    147    100.0     1.12      81.5   21.36  0.0228  0.0332
1.86 - 1.62     149    149    100.0     1.08      61.9   15.71  0.0248  0.0454
1.62 - 1.47     148    148    100.0     1.10      38.7   11.73  0.0359  0.0688
1.47 - 1.36     146    146    100.0     1.06      30.0    9.05  0.0627  0.0907
1.36 - 1.28     147    147    100.0     1.08      19.0    6.03  0.0756  0.1407
1.28 - 1.21     156    156    100.0     1.06      21.1    6.46  0.0842  0.1348
1.21 - 1.16     151    151    100.0     1.08      17.3    5.38  0.1017  0.1673
1.16 - 1.11     160    160    100.0     1.06      13.5    4.44  0.0850  0.2050
1.11 - 1.07     144    144    100.0     1.05       9.7    3.69  0.0831  0.2744
1.07 - 1.04     137    137    100.0     1.06       8.2    3.14  0.1270  0.3269
1.04 - 1.01     156    156    100.0     1.06       6.1    2.54  0.1415  0.4190
1.01 - 0.98     168    168    100.0     1.05       2.8    1.16  0.0975  1.0319
0.98 - 0.95     171    171    100.0     1.05       3.1    1.29  0.2413  0.8891
0.95 - 0.93     146    146    100.0     1.07       1.8    0.78  0.2963  1.4404
0.93 - 0.92      86     86    100.0     1.06       2.8    1.29  0.0743  0.8929
0.92 - 0.90     157    157    100.0     1.04       2.0    0.88  0.0564  1.3276
0.90 - 0.88     160    160    100.0     1.04       1.5    0.73  0.4710  1.6245
0.88 - 0.86     190    190    100.0     1.06       1.5    0.76  0.2326  1.4930
0.86 - 0.85      90     90    100.0     1.04       1.5    0.80  0.5985  1.3896
#------------------------------------------------------------------------------
0.95 - 0.85     829    829    100.0     1.05       1.8    0.84  0.1738  1.3626
 Inf - 0.85    2957   2958    100.0     1.07      32.3    7.67  0.0310  0.0831
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1273P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2047
_refine_ls_number_parameters     263
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2147
_refine_ls_wR_factor_gt          0.1883
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.061

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.5248(2) 0.14808(7) 0.38772(19) 0.0698(6) Uani 1 1 d . . . . .
S12 S 0.6187(4) 0.14410(9) 0.7296(2) 0.1260(11) Uani 1 1 d . . . . .
O11 O 0.5128(6) 0.1257(2) 0.2448(5) 0.0818(14) Uani 1 1 d . . . . .
O12 O 0.6502(5) 0.1909(2) 0.4301(5) 0.0878(15) Uani 1 1 d . . . . .
N11 N -0.0659(7) 0.2703(3) 0.5188(7) 0.098(2) Uani 1 1 d . . . . .
H10 H -0.067413 0.301441 0.578680 0.147 Uiso 1 1 d R U . . .
H11 H -0.151713 0.256242 0.478380 0.147 Uiso 1 1 d R U . . .
N12 N 0.5316(7) 0.0821(2) 0.4782(6) 0.0699(15) Uani 1 1 d . . . . .
N13 N 0.5666(7) 0.0261(2) 0.6852(6) 0.0816(18) Uani 1 1 d . . . . .
H17 H 0.543726 -0.010262 0.644927 0.122 Uiso 1 1 calc R U . . .
C11 C 0.0723(9) 0.2427(3) 0.4871(8) 0.0692(18) Uani 1 1 d . . . . .
C12 C 0.0745(8) 0.1929(3) 0.3880(7) 0.0725(19) Uani 1 1 d . . . . .
H12 H -0.018560 0.178443 0.343162 0.087 Uiso 1 1 calc R U . . .
C13 C 0.2112(9) 0.1656(3) 0.3570(7) 0.0673(18) Uani 1 1 d . . . . .
H13 H 0.211366 0.132189 0.291402 0.081 Uiso 1 1 calc R U . . .
C14 C 0.3509(8) 0.1867(3) 0.4217(6) 0.0620(17) Uani 1 1 d . . . . .
C15 C 0.3492(9) 0.2367(3) 0.5192(7) 0.0677(18) Uani 1 1 d . . . . .
H15 H 0.442797 0.251254 0.562736 0.081 Uiso 1 1 calc R U . . .
C16 C 0.2129(9) 0.2645(3) 0.5519(7) 0.0712(19) Uani 1 1 d . . . . .
H16 H 0.213248 0.298055 0.617160 0.085 Uiso 1 1 calc R U . . .
C17 C 0.5676(9) 0.0817(3) 0.6148(8) 0.0749(19) Uani 1 1 d . . . . .
C18 C 0.6052(12) 0.0311(4) 0.8290(8) 0.116(3) Uani 1 1 d . . . . .
H18 H 0.610137 -0.004057 0.890256 0.139 Uiso 1 1 calc R U . . .
C19 C 0.6340(15) 0.0911(4) 0.8683(10) 0.145(4) Uani 1 1 d . . . . .
H19 H 0.659770 0.103469 0.960807 0.174 Uiso 1 1 calc R U . . .
O30 O 0.203(2) 0.0247(10) 0.8979(19) 0.171(7) Uani 0.580(15) 1 d D U P A 1
O31 O 0.143(2) 0.1112(9) 1.0287(19) 0.224(9) Uani 0.580(15) 1 d D U P A 1
C30 C 0.1416(18) 0.0876(7) 0.9215(13) 0.171(5) Uani 0.580(15) 1 d D U P A 1
C31 C 0.078(2) 0.1202(7) 0.7940(16) 0.121(6) Uani 0.580(15) 1 d D U P A 1
H31A H 0.160219 0.145151 0.754795 0.145 Uiso 0.580(15) 1 calc R U P A 1
H31B H -0.002141 0.150449 0.819976 0.145 Uiso 0.580(15) 1 calc R U P A 1
C32 C 0.006(2) 0.0746(8) 0.6791(17) 0.146(8) Uani 0.580(15) 1 d D U P A 1
H32A H -0.020203 0.098579 0.593264 0.175 Uiso 0.580(15) 1 calc R U P A 1
H32B H -0.088061 0.054618 0.709978 0.175 Uiso 0.580(15) 1 calc R U P A 1
C33 C 0.130(3) 0.0224(10) 0.6532(19) 0.198(12) Uani 0.580(15) 1 d D U P A 1
H33A H 0.090383 -0.006626 0.579182 0.237 Uiso 0.580(15) 1 calc R U P A 1
H33B H 0.223552 0.042998 0.622222 0.237 Uiso 0.580(15) 1 calc R U P A 1
C34 C 0.171(3) -0.0161(8) 0.786(2) 0.146(9) Uani 0.580(15) 1 d D U P A 1
H34A H 0.084118 -0.044186 0.805615 0.175 Uiso 0.580(15) 1 calc R U P A 1
H34B H 0.261081 -0.043162 0.772628 0.175 Uiso 0.580(15) 1 calc R U P A 1
O30A O 0.114(3) 0.0223(11) 0.9367(18) 0.157(9) Uani 0.420(15) 1 d D U P A 2
O31A O 0.091(5) -0.0743(12) 0.833(4) 0.39(3) Uani 0.420(15) 1 d D U P A 2
C30A C 0.102(4) -0.0204(9) 0.817(2) 0.168(16) Uani 0.420(15) 1 d D U P A 2
C31A C 0.026(4) 0.0132(13) 0.696(3) 0.230(19) Uani 0.420(15) 1 d D U P A 2
H31C H -0.081936 0.020860 0.714085 0.276 Uiso 0.420(15) 1 calc R U P A 2
H31D H 0.027818 -0.015094 0.614717 0.276 Uiso 0.420(15) 1 calc R U P A 2
C32A C 0.101(4) 0.0783(12) 0.6588(18) 0.159(13) Uani 0.420(15) 1 d D U P A 2
H32C H 0.159881 0.073074 0.575824 0.191 Uiso 0.420(15) 1 calc R U P A 2
H32D H 0.019976 0.110160 0.637779 0.191 Uiso 0.420(15) 1 calc R U P A 2
C33A C 0.210(3) 0.1022(14) 0.782(2) 0.197(15) Uani 0.420(15) 1 d D U P A 2
H33C H 0.310910 0.081173 0.778658 0.237 Uiso 0.420(15) 1 calc R U P A 2
H33D H 0.225840 0.148523 0.773143 0.237 Uiso 0.420(15) 1 calc R U P A 2
C34A C 0.1416(18) 0.0876(7) 0.9215(13) 0.171(5) Uani 0.420(15) 1 d D U P A 2
H34C H 0.213361 0.102243 0.997828 0.205 Uiso 0.420(15) 1 calc R U P A 2
H34D H 0.044487 0.111181 0.927185 0.205 Uiso 0.420(15) 1 calc R U P A 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.431(5) . ?
S11 O11 1.434(5) . ?
S11 N12 1.611(5) . ?
S11 C14 1.741(7) . ?
S12 C19 1.713(9) . ?
S12 C17 1.729(7) . ?
N11 C11 1.368(8) . ?
N11 H10 0.8595 . ?
N11 H11 0.8596 . ?
N12 C17 1.317(8) . ?
N13 C17 1.330(8) . ?
N13 C18 1.391(9) . ?
N13 H17 0.8600 . ?
C11 C16 1.394(9) . ?
C11 C12 1.397(9) . ?
C12 C13 1.352(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(8) . ?
C15 C16 1.358(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.315(11) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O30 C34 1.37(2) . ?
O30 C30 1.42(2) . ?
O31 C30 1.130(16) . ?
C30 C31 1.464(16) . ?
C31 C32 1.541(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.546(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.516(8) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
O30A C34A 1.38(2) . ?
O30A C30A 1.44(2) . ?
O31A C30A 1.129(18) . ?
C30A C31A 1.462(18) . ?
C31A C32A 1.540(8) . ?
C31A H31C 0.9700 . ?
C31A H31D 0.9700 . ?
C32A C33A 1.533(8) . ?
C32A H32C 0.9700 . ?
C32A H32D 0.9700 . ?
C33A C34A 1.519(8) . ?
C33A H33C 0.9700 . ?
C33A H33D 0.9700 . ?
C34A H34C 0.9700 . ?
C34A H34D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 118.3(3) . . ?
O12 S11 N12 111.8(3) . . ?
O11 S11 N12 103.5(3) . . ?
O12 S11 C14 107.6(3) . . ?
O11 S11 C14 108.2(3) . . ?
N12 S11 C14 106.9(3) . . ?
C19 S12 C17 90.8(4) . . ?
C11 N11 H10 120.5 . . ?
C11 N11 H11 119.4 . . ?
H10 N11 H11 120.1 . . ?
C17 N12 S11 122.2(4) . . ?
C17 N13 C18 115.1(6) . . ?
C17 N13 H17 122.5 . . ?
C18 N13 H17 122.5 . . ?
N11 C11 C16 120.4(6) . . ?
N11 C11 C12 120.4(7) . . ?
C16 C11 C12 119.3(7) . . ?
C13 C12 C11 120.3(6) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.7(6) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 119.1(6) . . ?
C13 C14 S11 120.1(5) . . ?
C15 C14 S11 120.7(5) . . ?
C16 C15 C14 120.9(6) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 119.7(6) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
N12 C17 N13 119.7(6) . . ?
N12 C17 S12 130.7(5) . . ?
N13 C17 S12 109.5(5) . . ?
C19 C18 N13 112.2(8) . . ?
C19 C18 H18 123.9 . . ?
N13 C18 H18 123.9 . . ?
C18 C19 S12 112.3(7) . . ?
C18 C19 H19 123.8 . . ?
S12 C19 H19 123.8 . . ?
C34 O30 C30 128.8(13) . . ?
O31 C30 O30 123.6(17) . . ?
O31 C30 C31 122.1(17) . . ?
O30 C30 C31 114.3(12) . . ?
C30 C31 C32 114.7(10) . . ?
C30 C31 H31A 108.6 . . ?
C32 C31 H31A 108.6 . . ?
C30 C31 H31B 108.6 . . ?
C32 C31 H31B 108.6 . . ?
H31A C31 H31B 107.6 . . ?
C31 C32 C33 107.0(10) . . ?
C31 C32 H32A 110.3 . . ?
C33 C32 H32A 110.3 . . ?
C31 C32 H32B 110.3 . . ?
C33 C32 H32B 110.3 . . ?
H32A C32 H32B 108.6 . . ?
C34 C33 C32 110.9(10) . . ?
C34 C33 H33A 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 108.0 . . ?
O30 C34 C33 110.4(13) . . ?
O30 C34 H34A 109.6 . . ?
C33 C34 H34A 109.6 . . ?
O30 C34 H34B 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
C34A O30A C30A 121.4(14) . . ?
O31A C30A O30A 120(2) . . ?
O31A C30A C31A 123(2) . . ?
O30A C30A C31A 109.9(16) . . ?
C30A C31A C32A 115.2(13) . . ?
C30A C31A H31C 108.5 . . ?
C32A C31A H31C 108.5 . . ?
C30A C31A H31D 108.5 . . ?
C32A C31A H31D 108.5 . . ?
H31C C31A H31D 107.5 . . ?
C33A C32A C31A 110.4(10) . . ?
C33A C32A H32C 109.6 . . ?
C31A C32A H32C 109.6 . . ?
C33A C32A H32D 109.6 . . ?
C31A C32A H32D 109.6 . . ?
H32C C32A H32D 108.1 . . ?
C34A C33A C32A 110.7(11) . . ?
C34A C33A H33C 109.5 . . ?
C32A C33A H33C 109.5 . . ?
C34A C33A H33D 109.5 . . ?
C32A C33A H33D 109.5 . . ?
H33C C33A H33D 108.1 . . ?
O30A C34A C33A 111.4(14) . . ?
O30A C34A H34C 109.3 . . ?
C33A C34A H34C 109.3 . . ?
O30A C34A H34D 109.3 . . ?
C33A C34A H34D 109.4 . . ?
H34C C34A H34D 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 40.7(7) . . . . ?
O11 S11 N12 C17 169.0(6) . . . . ?
C14 S11 N12 C17 -76.8(6) . . . . ?
N11 C11 C12 C13 -179.9(6) . . . . ?
C16 C11 C12 C13 1.0(10) . . . . ?
C11 C12 C13 C14 -0.5(10) . . . . ?
C12 C13 C14 C15 -0.1(9) . . . . ?
C12 C13 C14 S11 176.5(5) . . . . ?
O12 S11 C14 C13 161.9(5) . . . . ?
O11 S11 C14 C13 33.0(6) . . . . ?
N12 S11 C14 C13 -77.9(5) . . . . ?
O12 S11 C14 C15 -21.5(6) . . . . ?
O11 S11 C14 C15 -150.4(5) . . . . ?
N12 S11 C14 C15 98.7(5) . . . . ?
C13 C14 C15 C16 0.3(9) . . . . ?
S11 C14 C15 C16 -176.3(5) . . . . ?
C14 C15 C16 C11 0.2(10) . . . . ?
N11 C11 C16 C15 -179.9(6) . . . . ?
C12 C11 C16 C15 -0.8(10) . . . . ?
S11 N12 C17 N13 177.8(5) . . . . ?
S11 N12 C17 S12 -1.7(10) . . . . ?
C18 N13 C17 N12 -179.6(7) . . . . ?
C18 N13 C17 S12 0.0(9) . . . . ?
C19 S12 C17 N12 179.0(9) . . . . ?
C19 S12 C17 N13 -0.6(7) . . . . ?
C17 N13 C18 C19 0.8(13) . . . . ?
N13 C18 C19 S12 -1.2(14) . . . . ?
C17 S12 C19 C18 1.1(10) . . . . ?
C34 O30 C30 O31 160(2) . . . . ?
C34 O30 C30 C31 -21(3) . . . . ?
O31 C30 C31 C32 -150(2) . . . . ?
O30 C30 C31 C32 31(2) . . . . ?
C30 C31 C32 C33 -51.8(19) . . . . ?
C31 C32 C33 C34 61(2) . . . . ?
C30 O30 C34 C33 30(3) . . . . ?
C32 C33 C34 O30 -49(2) . . . . ?
C34A O30A C30A O31A 174(4) . . . . ?
C34A O30A C30A C31A -35(3) . . . . ?
O31A C30A C31A C32A -157(5) . . . . ?
O30A C30A C31A C32A 53(4) . . . . ?
C30A C31A C32A C33A -16(4) . . . . ?
C31A C32A C33A C34A -38(4) . . . . ?
C30A O30A C34A C33A -20(3) . . . . ?
C32A C33A C34A O30A 58(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.86 2.26 3.083(8) 161.0 4_566 yes
N11 H11 O12 0.86 2.20 3.013(8) 158.7 1_455 yes
N13 H17 S11 0.86 2.92 3.737(5) 159.6 3_656 yes
N13 H17 N12 0.86 1.97 2.821(7) 167.9 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_40
_database_code_depnum_ccdc_archive 'CCDC 2120802'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 14n
#===============================================================================
# start Validation Reply Form
_vrf_PLAT029_40                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.850 Why?  
RESPONSE: The missing data are distributed evenly through reciprocal space 
and there is no adverse impact on the refinement.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, cyclopropanecarbonitrile (1:1) solvate'
_chemical_name_common            
'Sulfathiazole, cyclopropanecarbonitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C4 H5 N'
_chemical_formula_sum            'C13 H14 N4 O2 S2'
_chemical_formula_weight         322.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.179(2)
_cell_length_b                   16.907(3)
_cell_length_c                   39.202(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6084(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17034
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      24.91

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             2688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.359
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17034
_diffrn_reflns_av_unetI/netI     0.2267
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.409
_diffrn_reflns_theta_max         24.908
_diffrn_reflns_theta_full        24.908
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measured_fraction_theta_full 0.850
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_Laue_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_point_group_measured_fraction_full 0.850
_reflns_number_total             4506
_reflns_number_gt                1995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  14n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.96      74     85     87.1     4.05     346.0   30.42  0.0745  0.0254
3.96 - 2.55     174    187     93.0     4.10     229.1   16.87  0.0900  0.0420
2.55 - 2.00     250    256     97.7     4.32     110.7   10.09  0.0561  0.0791
2.00 - 1.73     242    254     95.3     4.33      82.0    7.73  0.0760  0.1045
1.73 - 1.55     259    268     96.6     4.32      69.7    6.59  0.0908  0.1254
1.55 - 1.44     252    257     98.1     4.04      52.0    4.82  0.0783  0.1799
1.44 - 1.35     247    253     97.6     4.28      53.2    4.92  0.0912  0.1721
1.35 - 1.28     240    248     96.8     4.04      42.9    3.95  0.1002  0.2356
1.28 - 1.22     260    273     95.2     3.92      40.2    3.52  0.1000  0.2729
1.22 - 1.17     255    260     98.1     4.01      48.6    3.81  0.1033  0.2312
1.17 - 1.13     226    233     97.0     3.89      43.2    3.21  0.1155  0.2697
1.13 - 1.09     276    293     94.2     3.35      33.1    2.47  0.1199  0.3720
1.09 - 1.06     218    228     95.6     3.29      27.0    2.03  0.1429  0.4580
1.06 - 1.03     256    266     96.2     3.27      27.8    2.07  0.1415  0.4709
1.03 - 1.00     279    301     92.7     2.90      22.7    1.67  0.1793  0.5966
1.00 - 0.98     210    227     92.5     2.68      19.7    1.41  0.1858  0.7136
0.98 - 0.95     322    357     90.2     2.55      16.9    1.27  0.1989  0.8335
0.95 - 0.93     233    262     88.9     2.47      20.7    1.33  0.1803  0.7170
0.93 - 0.91     234    291     80.4     2.04      16.0    1.05  0.2124  0.9580
0.91 - 0.89     181    314     57.6     1.30      15.1    1.04  0.1801  0.9995
0.89 - 0.84     254    853     29.8     0.58      16.4    0.97  0.2311  1.0505
#------------------------------------------------------------------------------
0.94 - 0.84     785   1590     49.4     1.16      16.5    1.07  0.2058  0.9526
 Inf - 0.84    4942   5966     82.8     2.98      51.3    4.27  0.0973  0.2331
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4506
_refine_ls_number_parameters     379
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   0.660
_refine_ls_restrained_S_all      0.668
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.055

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.45050(11) 0.58995(7) 0.79995(3) 0.0215(3) Uani 1 1 d . . . . .
S12 S 0.80395(10) 0.59324(8) 0.78823(3) 0.0280(3) Uani 1 1 d . . . . .
O11 O 0.3176(2) 0.55613(15) 0.81346(8) 0.0270(8) Uani 1 1 d . . . . .
O12 O 0.5109(2) 0.55458(16) 0.76929(8) 0.0239(8) Uani 1 1 d . . . . .
N11 N 0.3445(3) 0.9278(2) 0.77261(11) 0.0445(12) Uani 1 1 d . . . . .
H10 H 0.396025 0.952141 0.756102 0.067 Uiso 1 1 d R U . . .
H11 H 0.277495 0.955141 0.784792 0.067 Uiso 1 1 d R U . . .
N12 N 0.5623(3) 0.5854(2) 0.83135(8) 0.0196(9) Uani 1 1 d . . . . .
N13 N 0.7973(3) 0.5903(2) 0.85223(9) 0.0241(9) Uani 1 1 d . . . . .
H17 H 0.767037 0.588149 0.873510 0.036 Uiso 1 1 calc R U . . .
C11 C 0.3694(4) 0.8503(3) 0.77888(13) 0.0269(12) Uani 1 1 d . . . . .
C12 C 0.2899(4) 0.8095(3) 0.80346(12) 0.0283(12) Uani 1 1 d . . . . .
H12 H 0.218143 0.837055 0.816258 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3124(4) 0.7311(3) 0.80964(12) 0.0244(12) Uani 1 1 d . . . . .
H13 H 0.256708 0.704632 0.826586 0.029 Uiso 1 1 calc R U . . .
C14 C 0.4175(4) 0.6898(2) 0.79100(11) 0.0185(11) Uani 1 1 d . . . . .
C15 C 0.4978(4) 0.7293(3) 0.76669(12) 0.0236(12) Uani 1 1 d . . . . .
H15 H 0.570013 0.701650 0.754076 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4745(4) 0.8084(3) 0.76047(12) 0.0290(13) Uani 1 1 d . . . . .
H16 H 0.530376 0.834776 0.743530 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7050(4) 0.5897(2) 0.82559(11) 0.0177(10) Uani 1 1 d . . . . .
C18 C 0.9427(4) 0.5943(3) 0.84376(12) 0.0272(12) Uani 1 1 d . . . . .
H18 H 1.018861 0.594870 0.860170 0.033 Uiso 1 1 calc R U . . .
C19 C 0.9655(4) 0.5973(3) 0.81076(12) 0.0264(12) Uani 1 1 d . . . . .
H19 H 1.059041 0.601267 0.800539 0.032 Uiso 1 1 calc R U . . .
S21 S 0.75540(11) 0.58939(8) 0.94840(3) 0.0267(3) Uani 1 1 d . . . . .
S22 S 0.43117(12) 0.51127(8) 0.95711(4) 0.0364(4) Uani 1 1 d . . . . .
O21 O 0.9012(2) 0.59615(18) 0.93507(8) 0.0325(9) Uani 1 1 d . . . . .
O22 O 0.7314(3) 0.53601(17) 0.97667(8) 0.0285(8) Uani 1 1 d . . . . .
N21 N 0.5715(4) 0.9053(2) 0.99465(11) 0.0573(14) Uani 1 1 d . . . . .
H20 H 0.512740 0.910396 1.012949 0.086 Uiso 1 1 d R U . . .
H21 H 0.602180 0.948706 0.983389 0.086 Uiso 1 1 d R U . . .
N22 N 0.6587(3) 0.5653(2) 0.91593(9) 0.0230(10) Uani 1 1 d . . . . .
N23 N 0.4378(3) 0.5256(2) 0.89322(10) 0.0251(10) Uani 1 1 d . . . . .
H27 H 0.466707 0.535559 0.872249 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6155(5) 0.8320(3) 0.98336(14) 0.0364(14) Uani 1 1 d . . . . .
C22 C 0.7049(4) 0.8235(3) 0.95526(13) 0.0316(13) Uani 1 1 d . . . . .
H22 H 0.737833 0.868998 0.943289 0.038 Uiso 1 1 calc R U . . .
C23 C 0.7460(4) 0.7500(3) 0.94470(13) 0.0297(13) Uani 1 1 d . . . . .
H23 H 0.807594 0.744898 0.925343 0.036 Uiso 1 1 calc R U . . .
C24 C 0.6996(4) 0.6825(3) 0.96173(12) 0.0238(12) Uani 1 1 d . . . . .
C25 C 0.6106(4) 0.6908(3) 0.98988(13) 0.0354(14) Uani 1 1 d . . . . .
H25 H 0.578869 0.645333 1.001996 0.042 Uiso 1 1 calc R U . . .
C26 C 0.5681(4) 0.7644(3) 1.00039(14) 0.0408(15) Uani 1 1 d . . . . .
H26 H 0.505472 0.769543 1.019551 0.049 Uiso 1 1 calc R U . . .
C27 C 0.5251(5) 0.5368(2) 0.92054(12) 0.0236(12) Uani 1 1 d . . . . .
C28 C 0.3013(5) 0.4976(3) 0.90044(13) 0.0306(13) Uani 1 1 d . . . . .
H28 H 0.230658 0.486501 0.883391 0.037 Uiso 1 1 calc R U . . .
C29 C 0.2774(5) 0.4878(3) 0.93304(13) 0.0329(14) Uani 1 1 d . . . . .
H29 H 0.187781 0.470022 0.942418 0.040 Uiso 1 1 calc R U . . .
N31 N 0.4923(5) 0.9182(3) 0.87646(18) 0.120(3) Uani 1 1 d D . . . .
C31 C 0.7539(5) 0.8019(3) 0.83362(15) 0.062(2) Uani 1 1 d D . . . .
H31A H 0.836448 0.765462 0.837701 0.074 Uiso 1 1 calc R U . . .
H31B H 0.662991 0.776212 0.825756 0.074 Uiso 1 1 calc R U . . .
C32 C 0.7869(6) 0.8808(3) 0.82056(15) 0.0694(18) Uani 1 1 d D . . . .
H32A H 0.890329 0.894081 0.816275 0.083 Uiso 1 1 calc R U . . .
H32B H 0.717010 0.904822 0.804339 0.083 Uiso 1 1 calc R U . . .
C33 C 0.7406(5) 0.8718(3) 0.85591(14) 0.0487(16) Uani 1 1 d D . . . .
H33A H 0.820326 0.877620 0.873108 0.058 Uiso 1 1 calc R U . . .
C34 C 0.6008(5) 0.8987(3) 0.86716(17) 0.065(2) Uani 1 1 d D . . . .
N41 N 0.0524(5) 0.8138(3) 0.88159(16) 0.097(2) Uani 1 1 d D . . . .
C41 C 0.2857(7) 0.7006(4) 0.93100(19) 0.111(3) Uani 1 1 d D . . . .
H41A H 0.206528 0.663055 0.925392 0.133 Uiso 1 1 calc R U . . .
H41B H 0.327198 0.694521 0.954159 0.133 Uiso 1 1 calc R U . . .
C42 C 0.3837(5) 0.7235(4) 0.90383(16) 0.071(2) Uani 1 1 d D . . . .
H42A H 0.487179 0.732828 0.909647 0.086 Uiso 1 1 calc R U . . .
H42B H 0.366233 0.701290 0.880814 0.086 Uiso 1 1 calc R U . . .
C43 C 0.2763(7) 0.7768(4) 0.91769(19) 0.094(3) Uani 1 1 d D . . . .
H43A H 0.313287 0.820664 0.932412 0.113 Uiso 1 1 calc R U . . .
C44 C 0.1466(6) 0.7943(4) 0.89636(17) 0.074(2) Uani 1 1 d D . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.448(3) . ?
S11 O12 1.452(3) . ?
S11 N12 1.604(3) . ?
S11 C14 1.750(4) . ?
S12 C17 1.724(4) . ?
S12 C19 1.727(4) . ?
N11 C11 1.353(5) . ?
N11 H10 0.9013 . ?
N11 H11 0.9055 . ?
N12 C17 1.332(4) . ?
N13 C17 1.345(5) . ?
N13 C18 1.377(4) . ?
N13 H17 0.8800 . ?
C11 C12 1.391(6) . ?
C11 C16 1.397(6) . ?
C12 C13 1.364(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.398(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(5) . ?
C15 C16 1.376(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.311(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S21 O21 1.441(2) . ?
S21 O22 1.446(3) . ?
S21 N22 1.604(3) . ?
S21 C24 1.735(4) . ?
S22 C27 1.728(5) . ?
S22 C29 1.743(4) . ?
N21 C21 1.377(5) . ?
N21 H20 0.9016 . ?
N21 H21 0.9015 . ?
N22 C27 1.329(5) . ?
N23 C27 1.351(5) . ?
N23 C28 1.369(5) . ?
N23 H27 0.8800 . ?
C21 C22 1.381(6) . ?
C21 C26 1.392(6) . ?
C22 C23 1.363(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(6) . ?
C25 C26 1.368(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C28 C29 1.307(6) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
N31 C34 1.111(5) . ?
C31 C32 1.461(6) . ?
C31 C33 1.475(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.457(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.431(5) . ?
C33 H33A 1.0000 . ?
N41 C44 1.092(5) . ?
C41 C43 1.392(7) . ?
C41 C42 1.446(7) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.442(6) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.485(6) . ?
C43 H43A 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.50(17) . . ?
O11 S11 N12 103.83(18) . . ?
O12 S11 N12 111.78(16) . . ?
O11 S11 C14 107.95(17) . . ?
O12 S11 C14 107.3(2) . . ?
N12 S11 C14 108.1(2) . . ?
C17 S12 C19 91.1(2) . . ?
C11 N11 H10 119.0 . . ?
C11 N11 H11 120.9 . . ?
H10 N11 H11 120.1 . . ?
C17 N12 S11 119.8(3) . . ?
C17 N13 C18 115.1(4) . . ?
C17 N13 H17 122.5 . . ?
C18 N13 H17 122.5 . . ?
N11 C11 C12 121.1(4) . . ?
N11 C11 C16 120.9(4) . . ?
C12 C11 C16 118.0(4) . . ?
C13 C12 C11 121.7(4) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 119.8(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 S11 120.9(3) . . ?
C13 C14 S11 119.8(3) . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N12 C17 N13 119.2(4) . . ?
N12 C17 S12 131.6(3) . . ?
N13 C17 S12 109.1(3) . . ?
C19 C18 N13 113.2(4) . . ?
C19 C18 H18 123.4 . . ?
N13 C18 H18 123.4 . . ?
C18 C19 S12 111.5(3) . . ?
C18 C19 H19 124.3 . . ?
S12 C19 H19 124.3 . . ?
O21 S21 O22 117.95(18) . . ?
O21 S21 N22 104.26(18) . . ?
O22 S21 N22 111.45(18) . . ?
O21 S21 C24 108.2(2) . . ?
O22 S21 C24 106.9(2) . . ?
N22 S21 C24 107.8(2) . . ?
C27 S22 C29 90.7(2) . . ?
C21 N21 H20 121.1 . . ?
C21 N21 H21 118.9 . . ?
H20 N21 H21 119.9 . . ?
C27 N22 S21 119.6(3) . . ?
C27 N23 C28 115.3(4) . . ?
C27 N23 H27 122.3 . . ?
C28 N23 H27 122.3 . . ?
N21 C21 C22 121.6(5) . . ?
N21 C21 C26 119.5(5) . . ?
C22 C21 C26 118.9(5) . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 121.2(4) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C25 C24 C23 118.8(4) . . ?
C25 C24 S21 120.6(4) . . ?
C23 C24 S21 120.7(4) . . ?
C26 C25 C24 120.2(5) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 120.8(5) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
N22 C27 N23 119.4(4) . . ?
N22 C27 S22 131.6(4) . . ?
N23 C27 S22 109.1(3) . . ?
C29 C28 N23 113.5(4) . . ?
C29 C28 H28 123.2 . . ?
N23 C28 H28 123.2 . . ?
C28 C29 S22 111.4(4) . . ?
C28 C29 H29 124.3 . . ?
S22 C29 H29 124.3 . . ?
C32 C31 C33 59.5(3) . . ?
C32 C31 H31A 117.8 . . ?
C33 C31 H31A 117.8 . . ?
C32 C31 H31B 117.8 . . ?
C33 C31 H31B 117.8 . . ?
H31A C31 H31B 115.0 . . ?
C33 C32 C31 60.7(3) . . ?
C33 C32 H32A 117.7 . . ?
C31 C32 H32A 117.7 . . ?
C33 C32 H32B 117.7 . . ?
C31 C32 H32B 117.7 . . ?
H32A C32 H32B 114.8 . . ?
C34 C33 C32 121.4(5) . . ?
C34 C33 C31 120.8(5) . . ?
C32 C33 C31 59.8(3) . . ?
C34 C33 H33A 114.7 . . ?
C32 C33 H33A 114.7 . . ?
C31 C33 H33A 114.7 . . ?
N31 C34 C33 178.3(7) . . ?
C43 C41 C42 61.0(4) . . ?
C43 C41 H41A 117.7 . . ?
C42 C41 H41A 117.7 . . ?
C43 C41 H41B 117.7 . . ?
C42 C41 H41B 117.7 . . ?
H41A C41 H41B 114.8 . . ?
C43 C42 C41 57.6(3) . . ?
C43 C42 H42A 118.0 . . ?
C41 C42 H42A 118.0 . . ?
C43 C42 H42B 118.0 . . ?
C41 C42 H42B 118.0 . . ?
H42A C42 H42B 115.2 . . ?
C41 C43 C42 61.4(4) . . ?
C41 C43 C44 116.5(7) . . ?
C42 C43 C44 117.5(6) . . ?
C41 C43 H43A 116.7 . . ?
C42 C43 H43A 116.7 . . ?
C44 C43 H43A 116.7 . . ?
N41 C44 C43 173.8(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 160.5(3) . . . . ?
O12 S11 N12 C17 32.9(4) . . . . ?
C14 S11 N12 C17 -85.0(4) . . . . ?
N11 C11 C12 C13 178.9(4) . . . . ?
C16 C11 C12 C13 -0.1(7) . . . . ?
C11 C12 C13 C14 -0.1(7) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C12 C13 C14 S11 177.9(3) . . . . ?
O11 S11 C14 C15 -154.6(3) . . . . ?
O12 S11 C14 C15 -27.0(4) . . . . ?
N12 S11 C14 C15 93.7(4) . . . . ?
O11 S11 C14 C13 28.0(4) . . . . ?
O12 S11 C14 C13 155.6(3) . . . . ?
N12 S11 C14 C13 -83.7(4) . . . . ?
C13 C14 C15 C16 -0.6(7) . . . . ?
S11 C14 C15 C16 -178.0(3) . . . . ?
C14 C15 C16 C11 0.4(7) . . . . ?
N11 C11 C16 C15 -179.1(4) . . . . ?
C12 C11 C16 C15 0.0(7) . . . . ?
S11 N12 C17 N13 176.3(3) . . . . ?
S11 N12 C17 S12 -5.2(6) . . . . ?
C18 N13 C17 N12 179.5(4) . . . . ?
C18 N13 C17 S12 0.8(5) . . . . ?
C19 S12 C17 N12 -179.7(4) . . . . ?
C19 S12 C17 N13 -1.2(3) . . . . ?
C17 N13 C18 C19 0.3(6) . . . . ?
N13 C18 C19 S12 -1.2(6) . . . . ?
C17 S12 C19 C18 1.4(4) . . . . ?
O21 S21 N22 C27 164.7(3) . . . . ?
O22 S21 N22 C27 36.4(4) . . . . ?
C24 S21 N22 C27 -80.6(4) . . . . ?
N21 C21 C22 C23 -179.8(4) . . . . ?
C26 C21 C22 C23 -0.3(8) . . . . ?
C21 C22 C23 C24 0.0(7) . . . . ?
C22 C23 C24 C25 -0.2(7) . . . . ?
C22 C23 C24 S21 -178.9(3) . . . . ?
O21 S21 C24 C25 -145.3(4) . . . . ?
O22 S21 C24 C25 -17.4(4) . . . . ?
N22 S21 C24 C25 102.5(4) . . . . ?
O21 S21 C24 C23 33.3(4) . . . . ?
O22 S21 C24 C23 161.3(3) . . . . ?
N22 S21 C24 C23 -78.8(4) . . . . ?
C23 C24 C25 C26 0.8(7) . . . . ?
S21 C24 C25 C26 179.5(4) . . . . ?
C24 C25 C26 C21 -1.1(8) . . . . ?
N21 C21 C26 C25 -179.6(5) . . . . ?
C22 C21 C26 C25 0.9(8) . . . . ?
S21 N22 C27 N23 172.1(3) . . . . ?
S21 N22 C27 S22 -6.1(6) . . . . ?
C28 N23 C27 N22 -178.7(4) . . . . ?
C28 N23 C27 S22 -0.1(5) . . . . ?
C29 S22 C27 N22 177.7(4) . . . . ?
C29 S22 C27 N23 -0.6(3) . . . . ?
C27 N23 C28 C29 1.1(6) . . . . ?
N23 C28 C29 S22 -1.6(6) . . . . ?
C27 S22 C29 C28 1.3(4) . . . . ?
C31 C32 C33 C34 -109.8(6) . . . . ?
C32 C31 C33 C34 110.8(6) . . . . ?
C42 C41 C43 C44 108.3(7) . . . . ?
C41 C42 C43 C44 -106.8(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.90 2.17 3.009(5) 154.1 3_656 yes
N11 H11 O11 0.91 2.22 3.080(5) 157.8 8_665 yes
N13 H17 N22 0.88 1.98 2.834(5) 164.8 . yes
N21 H20 O21 0.90 2.28 3.168(5) 166.8 4_467 yes
N21 H21 O22 0.90 2.14 2.942(5) 147.6 8_765 yes
N23 H27 S11 0.88 2.98 3.817(4) 158.7 . yes
N23 H27 N12 0.88 2.01 2.865(5) 162.9 . yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_27
_database_code_depnum_ccdc_archive 'CCDC 2120799'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 28o
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_27                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.00 angstrom. Data were integrated to 0.84
angstrom resolution, but are truncated at 0.95 angstrom resolution for the
refinement.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 2,4,8,10-tetraspiro[5,5]undecane (1:1) solvate'
_chemical_name_common            'Sulfathiazole, tetraoxaspiroundecane solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C7 H12 O4'
_chemical_formula_sum            'C16 H21 N3 O6 S2'
_chemical_formula_weight         415.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   20.406(4)
_cell_length_b                   9.016(2)
_cell_length_c                   20.494(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3770.5(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12363
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      21.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.321
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12363
_diffrn_reflns_av_unetI/netI     0.1629
_diffrn_reflns_av_R_equivalents  0.1350
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         21.957
_diffrn_reflns_theta_full        21.957
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2266
_reflns_number_gt                1232
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  28o.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.80      48     59     81.4     5.15     440.3   31.42  0.1311  0.0198
3.80 - 2.53     111    117     94.9     5.05     185.5   17.29  0.1343  0.0453
2.53 - 1.98     162    166     97.6     5.67      99.8   11.97  0.1339  0.0747
1.98 - 1.70     165    169     97.6     6.04      76.2    9.24  0.1147  0.0958
1.70 - 1.55     153    156     98.1     5.62      49.5    6.08  0.1236  0.1389
1.55 - 1.43     169    171     98.8     5.40      48.6    5.18  0.1198  0.1630
1.43 - 1.35     145    147     98.6     5.84      39.7    5.07  0.1127  0.1911
1.35 - 1.27     175    178     98.3     5.63      36.3    4.30  0.1420  0.2142
1.27 - 1.21     167    171     97.7     5.18      43.1    4.07  0.1282  0.2089
1.21 - 1.16     172    174     98.9     5.19      33.5    3.52  0.1381  0.2740
1.16 - 1.12     141    147     95.9     4.62      33.7    3.04  0.1484  0.2970
1.12 - 1.08     182    189     96.3     4.34      29.6    2.71  0.1583  0.3418
1.08 - 1.05     152    159     95.6     4.29      21.0    2.13  0.1796  0.4903
1.05 - 1.02     155    161     96.3     4.01      21.7    2.15  0.1766  0.4812
1.02 - 0.99     187    203     92.1     3.72      20.5    1.92  0.1779  0.5359
0.99 - 0.97     118    127     92.9     3.59      16.4    1.57  0.1710  0.6640
0.97 - 0.95     159    167     95.2     3.60      14.4    1.40  0.2509  0.7518
0.95 - 0.93     147    162     90.7     3.31      11.9    1.17  0.2452  0.8905
0.93 - 0.91     162    178     91.0     3.13      11.1    1.12  0.2610  1.0142
0.91 - 0.88     185    309     59.9     1.94      11.3    1.06  0.2412  0.9538
0.88 - 0.84     130    443     29.3     0.73       9.6    0.87  0.2352  1.1625
#--------------------------------------------------------------------------------
0.94 - 0.84     551   1014     54.3     1.71      10.9    1.04  0.2492  1.0137
 Inf - 0.84    3185   3753     84.9     3.99      44.9    4.55  0.1392  0.2100
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0049P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2266
_refine_ls_number_parameters     251
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_restrained_S_all      0.761
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.075

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.39106(6) 0.77062(12) 0.52466(7) 0.0252(4) Uani 1 1 d . . . . .
S12 S 0.31515(6) 0.44639(12) 0.52569(8) 0.0316(4) Uani 1 1 d . . . . .
O11 O 0.43756(15) 0.8678(3) 0.55603(17) 0.0317(10) Uani 1 1 d . . . . .
O12 O 0.32758(15) 0.7491(3) 0.55407(16) 0.0298(9) Uani 1 1 d . . . . .
N11 N 0.3514(2) 1.0179(5) 0.2609(2) 0.0449(15) Uani 1 1 d D . . . .
H10 H 0.3171(19) 1.005(6) 0.238(2) 0.067 Uiso 1 1 d D U . . .
H11 H 0.3801(19) 1.063(5) 0.238(2) 0.067 Uiso 1 1 d D U . . .
N12 N 0.42934(17) 0.6146(4) 0.5156(2) 0.0205(10) Uani 1 1 d . . . . .
N13 N 0.42945(18) 0.3616(4) 0.50043(18) 0.0253(12) Uani 1 1 d . . . . .
H17 H 0.471997 0.359601 0.493469 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3590(3) 0.9617(5) 0.3211(3) 0.0281(14) Uani 1 1 d . . . . .
C12 C 0.4184(3) 0.9789(5) 0.3549(3) 0.0291(14) Uani 1 1 d . . . . .
H12 H 0.452774 1.033887 0.335103 0.035 Uiso 1 1 calc R U . . .
C13 C 0.4284(2) 0.9189(4) 0.4158(3) 0.0272(14) Uani 1 1 d . . . . .
H13 H 0.469385 0.932640 0.436966 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3795(2) 0.8385(5) 0.4465(2) 0.0203(13) Uani 1 1 d . . . . .
C15 C 0.3202(3) 0.8204(5) 0.4135(3) 0.0296(14) Uani 1 1 d . . . . .
H15 H 0.285904 0.766174 0.433773 0.035 Uiso 1 1 calc R U . . .
C16 C 0.3101(2) 0.8791(5) 0.3519(3) 0.0269(14) Uani 1 1 d . . . . .
H16 H 0.269491 0.863037 0.330439 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3976(2) 0.4878(5) 0.5132(2) 0.0193(12) Uani 1 1 d . . . . .
C18 C 0.3918(3) 0.2348(5) 0.4989(2) 0.0316(14) Uani 1 1 d . . . . .
H18 H 0.409001 0.138941 0.490214 0.038 Uiso 1 1 calc R U . . .
C19 C 0.3296(3) 0.2607(5) 0.5106(2) 0.0302(15) Uani 1 1 d . . . . .
H19 H 0.296552 0.186439 0.510778 0.036 Uiso 1 1 calc R U . . .
O30 O 0.49593(16) 0.4318(3) 0.71892(19) 0.0351(10) Uani 1 1 d . . . . .
O31 O 0.55019(19) 0.6250(4) 0.66587(19) 0.0453(11) Uani 1 1 d . . . . .
O32 O 0.63879(17) 0.6992(3) 0.82216(17) 0.0366(10) Uani 1 1 d . . . . .
O33 O 0.71901(17) 0.5308(4) 0.7883(2) 0.0461(11) Uani 1 1 d . . . . .
C30 C 0.5068(3) 0.5049(6) 0.6596(3) 0.0464(17) Uani 1 1 d . . . . .
H30A H 0.464454 0.541324 0.642405 0.056 Uiso 1 1 calc R U . . .
H30B H 0.524926 0.433407 0.627683 0.056 Uiso 1 1 calc R U . . .
C31 C 0.6127(3) 0.5761(5) 0.6878(3) 0.0402(16) Uani 1 1 d . . . . .
H31A H 0.642032 0.662727 0.693367 0.048 Uiso 1 1 calc R U . . .
H31B H 0.632408 0.509784 0.654687 0.048 Uiso 1 1 calc R U . . .
C32 C 0.6066(3) 0.4924(5) 0.7534(2) 0.0260(13) Uani 1 1 d . . . . .
C33 C 0.5557(2) 0.3722(5) 0.7447(3) 0.0323(15) Uani 1 1 d . . . . .
H33A H 0.572778 0.295439 0.714595 0.039 Uiso 1 1 calc R U . . .
H33B H 0.546843 0.324437 0.787271 0.039 Uiso 1 1 calc R U . . .
C34 C 0.5866(2) 0.5977(5) 0.8074(2) 0.0240(13) Uani 1 1 d . . . . .
H34A H 0.547244 0.654023 0.793828 0.029 Uiso 1 1 calc R U . . .
H34B H 0.575271 0.540242 0.847037 0.029 Uiso 1 1 calc R U . . .
C35 C 0.6952(3) 0.6201(6) 0.8396(3) 0.0462(17) Uani 1 1 d . . . . .
H35A H 0.685224 0.556345 0.877624 0.055 Uiso 1 1 calc R U . . .
H35B H 0.729798 0.690978 0.852765 0.055 Uiso 1 1 calc R U . . .
C36 C 0.6717(2) 0.4213(5) 0.7717(3) 0.0406(16) Uani 1 1 d . . . . .
H36A H 0.665171 0.353751 0.809219 0.049 Uiso 1 1 calc R U . . .
H36B H 0.688051 0.361749 0.734518 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.442(3) . ?
S11 O11 1.443(3) . ?
S11 N12 1.620(3) . ?
S11 C14 1.730(5) . ?
S12 C19 1.728(4) . ?
S12 C17 1.742(5) . ?
N11 C11 1.342(6) . ?
N11 H10 0.85(3) . ?
N11 H11 0.86(3) . ?
N12 C17 1.315(5) . ?
N13 C17 1.336(5) . ?
N13 C18 1.378(5) . ?
N13 H17 0.8800 . ?
C11 C16 1.396(6) . ?
C11 C12 1.406(7) . ?
C12 C13 1.374(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(6) . ?
C15 C16 1.383(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.313(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O30 C30 1.400(6) . ?
O30 C33 1.433(5) . ?
O31 C30 1.404(6) . ?
O31 C31 1.423(6) . ?
O32 C35 1.400(6) . ?
O32 C34 1.436(5) . ?
O33 C35 1.409(6) . ?
O33 C36 1.422(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.547(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.512(6) . ?
C32 C34 1.515(6) . ?
C32 C36 1.522(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 119.1(2) . . ?
O12 S11 N12 111.35(18) . . ?
O11 S11 N12 105.14(19) . . ?
O12 S11 C14 108.1(2) . . ?
O11 S11 C14 106.7(2) . . ?
N12 S11 C14 105.5(2) . . ?
C19 S12 C17 91.0(2) . . ?
C11 N11 H10 123(3) . . ?
C11 N11 H11 128(3) . . ?
H10 N11 H11 109.1(18) . . ?
C17 N12 S11 121.4(3) . . ?
C17 N13 C18 116.1(4) . . ?
C17 N13 H17 122.0 . . ?
C18 N13 H17 122.0 . . ?
N11 C11 C16 122.4(5) . . ?
N11 C11 C12 120.7(5) . . ?
C16 C11 C12 116.9(5) . . ?
C13 C12 C11 122.2(5) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 120.7(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 117.7(5) . . ?
C13 C14 S11 120.5(4) . . ?
C15 C14 S11 121.8(4) . . ?
C16 C15 C14 121.8(5) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C11 120.7(5) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N12 C17 N13 120.5(4) . . ?
N12 C17 S12 131.0(4) . . ?
N13 C17 S12 108.5(3) . . ?
C19 C18 N13 112.8(4) . . ?
C19 C18 H18 123.6 . . ?
N13 C18 H18 123.6 . . ?
C18 C19 S12 111.7(4) . . ?
C18 C19 H19 124.2 . . ?
S12 C19 H19 124.2 . . ?
C30 O30 C33 111.2(4) . . ?
C30 O31 C31 110.8(4) . . ?
C35 O32 C34 109.8(3) . . ?
C35 O33 C36 110.0(4) . . ?
O30 C30 O31 112.6(5) . . ?
O30 C30 H30A 109.1 . . ?
O31 C30 H30A 109.1 . . ?
O30 C30 H30B 109.1 . . ?
O31 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
O31 C31 C32 110.7(4) . . ?
O31 C31 H31A 109.5 . . ?
C32 C31 H31A 109.5 . . ?
O31 C31 H31B 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
C33 C32 C34 110.5(4) . . ?
C33 C32 C36 109.1(4) . . ?
C34 C32 C36 108.6(4) . . ?
C33 C32 C31 107.6(4) . . ?
C34 C32 C31 110.6(4) . . ?
C36 C32 C31 110.4(5) . . ?
O30 C33 C32 111.1(4) . . ?
O30 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
O30 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
O32 C34 C32 110.6(4) . . ?
O32 C34 H34A 109.5 . . ?
C32 C34 H34A 109.5 . . ?
O32 C34 H34B 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
O32 C35 O33 112.6(5) . . ?
O32 C35 H35A 109.1 . . ?
O33 C35 H35A 109.1 . . ?
O32 C35 H35B 109.1 . . ?
O33 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
O33 C36 C32 111.0(4) . . ?
O33 C36 H36A 109.4 . . ?
C32 C36 H36A 109.4 . . ?
O33 C36 H36B 109.4 . . ?
C32 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 22.6(5) . . . . ?
O11 S11 N12 C17 152.9(4) . . . . ?
C14 S11 N12 C17 -94.5(4) . . . . ?
N11 C11 C12 C13 -177.9(5) . . . . ?
C16 C11 C12 C13 -0.5(7) . . . . ?
C11 C12 C13 C14 -0.3(7) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C12 C13 C14 S11 -177.0(4) . . . . ?
O12 S11 C14 C13 156.4(4) . . . . ?
O11 S11 C14 C13 27.1(4) . . . . ?
N12 S11 C14 C13 -84.4(4) . . . . ?
O12 S11 C14 C15 -20.9(4) . . . . ?
O11 S11 C14 C15 -150.1(4) . . . . ?
N12 S11 C14 C15 98.4(4) . . . . ?
C13 C14 C15 C16 0.4(7) . . . . ?
S11 C14 C15 C16 177.7(4) . . . . ?
C14 C15 C16 C11 -1.2(7) . . . . ?
N11 C11 C16 C15 178.6(5) . . . . ?
C12 C11 C16 C15 1.3(7) . . . . ?
S11 N12 C17 N13 174.6(3) . . . . ?
S11 N12 C17 S12 -6.9(7) . . . . ?
C18 N13 C17 N12 -180.0(4) . . . . ?
C18 N13 C17 S12 1.2(5) . . . . ?
C19 S12 C17 N12 179.9(5) . . . . ?
C19 S12 C17 N13 -1.5(4) . . . . ?
C17 N13 C18 C19 -0.2(7) . . . . ?
N13 C18 C19 S12 -1.0(6) . . . . ?
C17 S12 C19 C18 1.4(4) . . . . ?
C33 O30 C30 O31 -60.9(5) . . . . ?
C31 O31 C30 O30 61.3(6) . . . . ?
C30 O31 C31 C32 -57.2(6) . . . . ?
O31 C31 C32 C33 52.8(5) . . . . ?
O31 C31 C32 C34 -67.9(5) . . . . ?
O31 C31 C32 C36 171.8(4) . . . . ?
C30 O30 C33 C32 57.0(6) . . . . ?
C34 C32 C33 O30 68.4(5) . . . . ?
C36 C32 C33 O30 -172.2(4) . . . . ?
C31 C32 C33 O30 -52.4(5) . . . . ?
C35 O32 C34 C32 -57.4(5) . . . . ?
C33 C32 C34 O32 171.8(4) . . . . ?
C36 C32 C34 O32 52.2(5) . . . . ?
C31 C32 C34 O32 -69.1(5) . . . . ?
C34 O32 C35 O33 63.0(5) . . . . ?
C36 O33 C35 O32 -62.8(6) . . . . ?
C35 O33 C36 C32 56.8(6) . . . . ?
C33 C32 C36 O33 -172.7(4) . . . . ?
C34 C32 C36 O33 -52.2(6) . . . . ?
C31 C32 C36 O33 69.2(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O33 0.85(3) 2.10(3) 2.918(6) 162(4) 4_466 yes
N11 H11 O30 0.86(3) 2.40(4) 3.105(6) 141(4) 7_575 yes
N11 H11 O32 0.86(3) 2.50(4) 3.074(5) 125(4) 5_676 yes
N13 H17 N12 0.88 2.04 2.908(5) 171.3 5_666 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_39
_database_code_depnum_ccdc_archive 'CCDC 2120805'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 13n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, propionitrile (1:1) solvate'
_chemical_name_common            'Sulfathiazole, propionitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C3 H5 N'
_chemical_formula_sum            'C12 H14 N4 O2 S2'
_chemical_formula_weight         310.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.045(2)
_cell_length_b                   16.864(3)
_cell_length_c                   39.421(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6013(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    21487
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             2592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.360
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21487
_diffrn_reflns_av_unetI/netI     0.1010
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         3.538
_diffrn_reflns_theta_max         25.040
_diffrn_reflns_theta_full        25.040
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             5055
_reflns_number_gt                2895
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  13n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.82      86     96     89.6     5.99     101.3   36.02  0.0500  0.0201
3.82 - 2.42     196    208     94.2     7.50      66.5   33.11  0.0422  0.0210
2.42 - 1.89     288    295     97.6     7.49      34.7   27.24  0.0566  0.0268
1.89 - 1.64     285    302     94.4     5.77      20.5   18.09  0.0741  0.0431
1.64 - 1.48     275    291     94.5     5.08      15.6   15.81  0.0793  0.0498
1.48 - 1.36     306    323     94.7     4.74      14.2   12.87  0.0889  0.0619
1.36 - 1.27     283    317     89.3     4.34      13.0   11.59  0.0973  0.0636
1.27 - 1.21     260    278     93.5     4.10      10.3    9.18  0.1084  0.0844
1.21 - 1.15     292    321     91.0     3.45      11.8    8.58  0.1051  0.0919
1.15 - 1.10     295    332     88.9     3.24       9.3    6.90  0.1234  0.1148
1.10 - 1.06     279    306     91.2     3.26       6.5    5.00  0.1628  0.1666
1.06 - 1.02     328    355     92.4     3.11       6.0    4.34  0.1848  0.1945
1.02 - 0.99     282    299     94.3     2.98       4.9    3.37  0.2156  0.2565
0.99 - 0.97     227    238     95.4     2.86       4.2    2.98  0.2332  0.3189
0.97 - 0.94     357    366     97.5     2.80       3.3    2.12  0.3075  0.4356
0.94 - 0.92     264    273     96.7     2.71       4.3    2.51  0.2792  0.3587
0.92 - 0.90     291    302     96.4     2.75       2.9    1.81  0.3719  0.5399
0.90 - 0.88     330    339     97.3     2.72       3.3    1.94  0.3249  0.4978
0.88 - 0.87     176    181     97.2     2.62       3.2    1.72  0.3650  0.5472
0.87 - 0.85     355    367     96.7     2.66       2.3    1.26  0.4656  0.7697
0.85 - 0.84     187    206     90.8     2.47       2.5    1.20  0.5062  0.7712
#------------------------------------------------------------------------------
0.94 - 0.84    1603   1668     96.1     2.67       3.1    1.75  0.3713  0.5488
 Inf - 0.84    5642   5995     94.1     3.83      12.6    8.70  0.0846  0.1001
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5055
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.067

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.44658(9) 0.58560(5) 0.80031(3) 0.0258(3) Uani 1 1 d . . . . .
S12 S 0.80480(10) 0.58989(6) 0.78949(3) 0.0353(3) Uani 1 1 d . . . . .
O11 O 0.3099(2) 0.55270(13) 0.81323(7) 0.0325(7) Uani 1 1 d . . . . .
O12 O 0.5089(2) 0.55063(13) 0.77003(6) 0.0310(7) Uani 1 1 d . . . . .
N11 N 0.3516(4) 0.92623(17) 0.77359(10) 0.0526(11) Uani 1 1 d . . . . .
H10 H 0.403197 0.950604 0.757083 0.079 Uiso 1 1 d R U . . .
H11 H 0.284657 0.953594 0.785763 0.079 Uiso 1 1 d R U . . .
N12 N 0.5586(3) 0.58008(15) 0.83180(8) 0.0244(7) Uani 1 1 d . . . . .
N13 N 0.7949(3) 0.58875(16) 0.85350(8) 0.0294(8) Uani 1 1 d . . . . .
H17 H 0.762583 0.587131 0.874543 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3750(4) 0.8480(2) 0.78000(11) 0.0330(10) Uani 1 1 d . . . . .
C12 C 0.2938(4) 0.8078(2) 0.80484(11) 0.0334(10) Uani 1 1 d . . . . .
H12 H 0.222808 0.836030 0.817859 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3144(3) 0.7290(2) 0.81072(10) 0.0280(9) Uani 1 1 d . . . . .
H13 H 0.258252 0.703086 0.827806 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4175(3) 0.68606(19) 0.79182(10) 0.0231(9) Uani 1 1 d . . . . .
C15 C 0.4998(4) 0.7254(2) 0.76709(10) 0.0284(9) Uani 1 1 d . . . . .
H15 H 0.570573 0.696914 0.754105 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4794(4) 0.8048(2) 0.76134(10) 0.0320(10) Uani 1 1 d . . . . .
H16 H 0.536728 0.830818 0.744510 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7041(4) 0.58629(19) 0.82687(10) 0.0244(9) Uani 1 1 d . . . . .
C18 C 0.9439(4) 0.5941(2) 0.84560(12) 0.0345(10) Uani 1 1 d . . . . .
H18 H 1.020455 0.595549 0.862074 0.041 Uiso 1 1 calc R U . . .
C19 C 0.9673(4) 0.5968(2) 0.81231(12) 0.0372(11) Uani 1 1 d . . . . .
H19 H 1.062273 0.602015 0.802261 0.045 Uiso 1 1 calc R U . . .
S21 S 0.74593(10) 0.58786(5) 0.94801(3) 0.0313(3) Uani 1 1 d . . . . .
S22 S 0.41512(11) 0.51312(7) 0.95696(3) 0.0473(3) Uani 1 1 d . . . . .
O21 O 0.8939(2) 0.59491(14) 0.93478(7) 0.0375(7) Uani 1 1 d . . . . .
O22 O 0.7233(2) 0.53359(13) 0.97588(7) 0.0358(7) Uani 1 1 d . . . . .
N21 N 0.5624(3) 0.90670(17) 0.99333(10) 0.0565(12) Uani 1 1 d . . . . .
H20 H 0.503664 0.911794 1.011630 0.085 Uiso 1 1 d R U . . .
H21 H 0.593104 0.950104 0.982070 0.085 Uiso 1 1 d R U . . .
N22 N 0.6460(3) 0.56464(17) 0.91574(8) 0.0310(8) Uani 1 1 d . . . . .
N23 N 0.4213(3) 0.52590(16) 0.89312(9) 0.0341(8) Uani 1 1 d . . . . .
H27 H 0.451380 0.534642 0.872223 0.051 Uiso 1 1 calc R U . . .
C21 C 0.6044(4) 0.8326(2) 0.98266(12) 0.0386(11) Uani 1 1 d . . . . .
C22 C 0.6956(4) 0.8229(2) 0.95441(11) 0.0377(11) Uani 1 1 d . . . . .
H22 H 0.728893 0.868110 0.942237 0.045 Uiso 1 1 calc R U . . .
C23 C 0.7376(4) 0.7485(2) 0.94406(10) 0.0330(10) Uani 1 1 d . . . . .
H23 H 0.800057 0.742663 0.924849 0.040 Uiso 1 1 calc R U . . .
C24 C 0.6894(4) 0.6820(2) 0.96145(11) 0.0306(10) Uani 1 1 d . . . . .
C25 C 0.5988(4) 0.6901(2) 0.98939(11) 0.0404(11) Uani 1 1 d . . . . .
H25 H 0.566044 0.644718 1.001521 0.049 Uiso 1 1 calc R U . . .
C26 C 0.5561(4) 0.7653(2) 0.99952(12) 0.0487(13) Uani 1 1 d . . . . .
H26 H 0.492134 0.770878 1.018479 0.058 Uiso 1 1 calc R U . . .
C27 C 0.5091(4) 0.5377(2) 0.92018(11) 0.0327(10) Uani 1 1 d . . . . .
C28 C 0.2800(4) 0.4990(2) 0.90048(13) 0.0439(12) Uani 1 1 d . . . . .
H28 H 0.207422 0.487448 0.883786 0.053 Uiso 1 1 calc R U . . .
C29 C 0.2583(4) 0.4913(2) 0.93350(13) 0.0473(12) Uani 1 1 d . . . . .
H29 H 0.166909 0.475626 0.943274 0.057 Uiso 1 1 calc R U . . .
N31 N 0.5321(4) 0.9141(2) 0.87560(13) 0.0797(15) Uani 1 1 d . . . . .
C31 C 0.6065(6) 0.8759(3) 0.86157(15) 0.0731(18) Uani 1 1 d . . . . .
C32 C 0.7051(6) 0.8118(3) 0.84272(16) 0.096(2) Uani 1 1 d . . . . .
H32A H 0.768506 0.782546 0.858913 0.115 Uiso 1 1 calc R U . . .
H32B H 0.643274 0.773577 0.830000 0.115 Uiso 1 1 calc R U . . .
C33 C 0.7914(6) 0.8596(4) 0.82033(18) 0.121(3) Uani 1 1 d . . . . .
H33A H 0.725612 0.889625 0.805311 0.182 Uiso 1 1 calc R U . . .
H33B H 0.855951 0.825534 0.806706 0.182 Uiso 1 1 calc R U . . .
H33C H 0.851784 0.896551 0.833616 0.182 Uiso 1 1 calc R U . . .
N41 N 0.0251(5) 0.8183(3) 0.88918(16) 0.122(2) Uani 1 1 d . . . . .
C41 C 0.1283(6) 0.8043(4) 0.90277(16) 0.087(2) Uani 1 1 d . . . . .
C42 C 0.2738(6) 0.7900(4) 0.92049(17) 0.101(2) Uani 1 1 d . . . . .
H42A H 0.347397 0.829204 0.912499 0.122 Uiso 1 1 calc R U . . .
H42B H 0.260828 0.797320 0.945221 0.122 Uiso 1 1 calc R U . . .
C43 C 0.3261(7) 0.7139(4) 0.91420(19) 0.134(3) Uani 1 1 d . . . . .
H43A H 0.247805 0.675302 0.918985 0.201 Uiso 1 1 calc R U . . .
H43B H 0.411410 0.703191 0.928811 0.201 Uiso 1 1 calc R U . . .
H43C H 0.355817 0.709569 0.890368 0.201 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.446(2) . ?
S11 O11 1.447(2) . ?
S11 N12 1.605(3) . ?
S11 C14 1.747(3) . ?
S12 C19 1.727(4) . ?
S12 C17 1.734(4) . ?
N11 C11 1.360(4) . ?
N11 H10 0.8999 . ?
N11 H11 0.9001 . ?
N12 C17 1.334(4) . ?
N13 C17 1.334(4) . ?
N13 C18 1.386(4) . ?
N13 H17 0.8800 . ?
C11 C12 1.399(5) . ?
C11 C16 1.401(5) . ?
C12 C13 1.361(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(5) . ?
C15 C16 1.370(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.330(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S21 O21 1.441(2) . ?
S21 O22 1.444(3) . ?
S21 N22 1.609(3) . ?
S21 C24 1.750(4) . ?
S22 C27 1.731(4) . ?
S22 C29 1.732(4) . ?
N21 C21 1.372(4) . ?
N21 H20 0.9001 . ?
N21 H21 0.8999 . ?
N22 C27 1.331(4) . ?
N23 C27 1.345(5) . ?
N23 C28 1.387(4) . ?
N23 H27 0.8800 . ?
C21 C26 1.386(5) . ?
C21 C22 1.396(5) . ?
C22 C23 1.372(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(5) . ?
C25 C26 1.384(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C28 C29 1.323(6) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
N31 C31 1.083(6) . ?
C31 C32 1.587(8) . ?
C32 C33 1.428(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
N41 C41 1.102(6) . ?
C41 C42 1.509(8) . ?
C42 C43 1.389(7) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 117.85(15) . . ?
O12 S11 N12 111.64(15) . . ?
O11 S11 N12 104.16(15) . . ?
O12 S11 C14 107.22(17) . . ?
O11 S11 C14 108.10(14) . . ?
N12 S11 C14 107.42(15) . . ?
C19 S12 C17 90.4(2) . . ?
C11 N11 H10 119.8 . . ?
C11 N11 H11 120.2 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 120.3(3) . . ?
C17 N13 C18 115.1(3) . . ?
C17 N13 H17 122.5 . . ?
C18 N13 H17 122.5 . . ?
N11 C11 C12 121.2(3) . . ?
N11 C11 C16 120.8(3) . . ?
C12 C11 C16 118.0(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 S11 121.0(3) . . ?
C13 C14 S11 120.1(3) . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.8(4) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N13 C17 N12 119.7(3) . . ?
N13 C17 S12 110.1(2) . . ?
N12 C17 S12 130.2(3) . . ?
C19 C18 N13 112.3(3) . . ?
C19 C18 H18 123.9 . . ?
N13 C18 H18 123.9 . . ?
C18 C19 S12 112.1(3) . . ?
C18 C19 H19 124.0 . . ?
S12 C19 H19 124.0 . . ?
O21 S21 O22 117.32(15) . . ?
O21 S21 N22 104.81(16) . . ?
O22 S21 N22 111.58(16) . . ?
O21 S21 C24 107.82(16) . . ?
O22 S21 C24 107.64(18) . . ?
N22 S21 C24 107.22(16) . . ?
C27 S22 C29 90.3(2) . . ?
C21 N21 H20 119.7 . . ?
C21 N21 H21 120.3 . . ?
H20 N21 H21 120.0 . . ?
C27 N22 S21 120.1(3) . . ?
C27 N23 C28 115.2(4) . . ?
C27 N23 H27 122.4 . . ?
C28 N23 H27 122.4 . . ?
N21 C21 C26 120.8(4) . . ?
N21 C21 C22 121.0(4) . . ?
C26 C21 C22 118.2(4) . . ?
C23 C22 C21 120.6(4) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.4(4) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 S21 120.4(3) . . ?
C23 C24 S21 119.5(3) . . ?
C24 C25 C26 119.2(4) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C21 121.6(4) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
N22 C27 N23 119.7(4) . . ?
N22 C27 S22 130.5(3) . . ?
N23 C27 S22 109.8(3) . . ?
C29 C28 N23 112.0(4) . . ?
C29 C28 H28 124.0 . . ?
N23 C28 H28 124.0 . . ?
C28 C29 S22 112.5(3) . . ?
C28 C29 H29 123.7 . . ?
S22 C29 H29 123.7 . . ?
N31 C31 C32 173.5(7) . . ?
C33 C32 C31 102.2(5) . . ?
C33 C32 H32A 111.3 . . ?
C31 C32 H32A 111.3 . . ?
C33 C32 H32B 111.3 . . ?
C31 C32 H32B 111.3 . . ?
H32A C32 H32B 109.2 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N41 C41 C42 176.3(6) . . ?
C43 C42 C41 111.2(5) . . ?
C43 C42 H42A 109.4 . . ?
C41 C42 H42A 109.4 . . ?
C43 C42 H42B 109.4 . . ?
C41 C42 H42B 109.4 . . ?
H42A C42 H42B 108.0 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 34.7(3) . . . . ?
O11 S11 N12 C17 162.9(2) . . . . ?
C14 S11 N12 C17 -82.5(3) . . . . ?
N11 C11 C12 C13 178.4(3) . . . . ?
C16 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C12 C13 C14 S11 178.3(3) . . . . ?
O12 S11 C14 C15 -24.7(3) . . . . ?
O11 S11 C14 C15 -152.7(3) . . . . ?
N12 S11 C14 C15 95.4(3) . . . . ?
O12 S11 C14 C13 157.6(3) . . . . ?
O11 S11 C14 C13 29.6(3) . . . . ?
N12 S11 C14 C13 -82.3(3) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
S11 C14 C15 C16 -178.0(3) . . . . ?
C14 C15 C16 C11 -0.4(6) . . . . ?
N11 C11 C16 C15 -178.0(3) . . . . ?
C12 C11 C16 C15 0.7(6) . . . . ?
C18 N13 C17 N12 179.1(3) . . . . ?
C18 N13 C17 S12 0.5(3) . . . . ?
S11 N12 C17 N13 174.0(2) . . . . ?
S11 N12 C17 S12 -7.7(4) . . . . ?
C19 S12 C17 N13 -1.2(3) . . . . ?
C19 S12 C17 N12 -179.7(3) . . . . ?
C17 N13 C18 C19 0.9(4) . . . . ?
N13 C18 C19 S12 -1.8(4) . . . . ?
C17 S12 C19 C18 1.8(3) . . . . ?
O21 S21 N22 C27 166.1(3) . . . . ?
O22 S21 N22 C27 38.1(3) . . . . ?
C24 S21 N22 C27 -79.5(3) . . . . ?
N21 C21 C22 C23 179.7(4) . . . . ?
C26 C21 C22 C23 -1.0(6) . . . . ?
C21 C22 C23 C24 0.3(6) . . . . ?
C22 C23 C24 C25 -0.1(6) . . . . ?
C22 C23 C24 S21 -179.4(3) . . . . ?
O21 S21 C24 C25 -145.6(3) . . . . ?
O22 S21 C24 C25 -18.1(3) . . . . ?
N22 S21 C24 C25 102.0(3) . . . . ?
O21 S21 C24 C23 33.7(3) . . . . ?
O22 S21 C24 C23 161.2(3) . . . . ?
N22 S21 C24 C23 -78.7(3) . . . . ?
C23 C24 C25 C26 0.5(6) . . . . ?
S21 C24 C25 C26 179.8(3) . . . . ?
C24 C25 C26 C21 -1.2(6) . . . . ?
N21 C21 C26 C25 -179.2(4) . . . . ?
C22 C21 C26 C25 1.4(6) . . . . ?
S21 N22 C27 N23 173.4(2) . . . . ?
S21 N22 C27 S22 -6.5(5) . . . . ?
C28 N23 C27 N22 -178.9(3) . . . . ?
C28 N23 C27 S22 0.9(4) . . . . ?
C29 S22 C27 N22 177.9(4) . . . . ?
C29 S22 C27 N23 -2.0(3) . . . . ?
C27 N23 C28 C29 1.1(5) . . . . ?
N23 C28 C29 S22 -2.6(5) . . . . ?
C27 S22 C29 C28 2.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.90 2.15 2.991(4) 155.5 3_656 yes
N11 H11 O11 0.90 2.17 3.021(4) 158.0 8_665 yes
N13 H17 O21 0.88 2.66 3.329(4) 133.8 . yes
N13 H17 N22 0.88 1.97 2.828(5) 163.6 . yes
N21 H20 O21 0.90 2.34 3.218(5) 166.1 4_467 yes
N21 H21 O22 0.90 2.19 2.968(4) 144.2 8_765 yes
N23 H27 N12 0.88 2.02 2.867(4) 162.2 . yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_62
_database_code_depnum_ccdc_archive 'CCDC 2120808'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 20n
#===============================================================================
# start Validation Reply Form
_vrf_PLAT029_62                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.879 Why?  
RESPONSE: These are the data that are available. They are essentially 100%
complete to ca 0.94 angstrom. In the 0.94-0.84 shell, the completeness drops
to 63%, which accounts for the overall low percentage. Despite this deficiency,
the refinement is good, and the structure is not in doubt.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, piperidine (1:1) salt'
_chemical_name_common            'Sulfathiazole, piperidine (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 S2 O2 -, C5 H12 N +'
_chemical_formula_sum            'C14 H20 N4 O2 S2'
_chemical_formula_weight         340.46
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.948(1)
_cell_length_b                   14.868(1)
_cell_length_c                   15.958(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1648.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6723
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      25.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.335
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6723
_diffrn_reflns_av_unetI/netI     0.1173
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.746
_diffrn_reflns_theta_max         25.132
_diffrn_reflns_theta_full        25.132
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.879
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_point_group_measured_fraction_full 0.833
_reflns_number_total             2457
_reflns_number_gt                1658
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.628
_reflns_Friedel_fraction_max     0.769
_reflns_Friedel_fraction_full    0.769

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  20n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 4.03      23     26     88.5     4.88     216.9  114.20  0.2012  0.0051
4.03 - 2.53      54     57     94.7     5.05     209.3   70.45  0.1895  0.0108
2.53 - 1.98      75     79     94.9     5.58      64.7   39.56  0.0750  0.0215
1.98 - 1.70      80     80    100.0     5.32      46.2   25.31  0.0600  0.0313
1.70 - 1.55      73     74     98.6     5.57      31.0   19.31  0.0444  0.0424
1.55 - 1.42      79     79    100.0     5.48      24.5   16.91  0.0451  0.0518
1.42 - 1.33      81     81    100.0     5.72      21.7   14.11  0.0498  0.0571
1.33 - 1.26      71     72     98.6     5.72      18.7   12.79  0.0570  0.0636
1.26 - 1.20      81     83     97.6     4.94      14.7    9.30  0.0566  0.0857
1.20 - 1.15      71     72     98.6     4.90      16.7    9.83  0.0552  0.0852
1.15 - 1.11      83     85     97.6     4.94      11.6    7.44  0.0764  0.1190
1.11 - 1.07      80     81     98.8     4.91       9.0    6.27  0.0839  0.1452
1.07 - 1.04      72     73     98.6     4.38       7.1    4.93  0.1010  0.1901
1.04 - 1.01      74     76     97.4     4.22       6.2    4.28  0.1009  0.2208
1.01 - 0.98      88     94     93.6     3.84       5.2    3.61  0.1146  0.2624
0.98 - 0.96      63     66     95.5     3.76       5.0    3.03  0.1299  0.2846
0.96 - 0.94      74     76     97.4     3.59       4.4    2.75  0.1348  0.3395
0.94 - 0.91      98    114     86.0     2.77       3.2    2.03  0.1733  0.4800
0.91 - 0.89      75     89     84.3     1.79       2.7    1.49  0.1582  0.6534
0.89 - 0.87      70     92     76.1     1.32       2.3    1.25  0.1376  0.7811
0.87 - 0.85      57    115     49.6     0.67       2.4    1.11  0.1890  0.8702
0.85 - 0.84       7     76      9.2     0.11       2.2    0.86  0.5590  1.0520
#------------------------------------------------------------------------------
0.94 - 0.84     307    486     63.2     1.40       2.7    1.52  0.1658  0.6565
 Inf - 0.84    1529   1740     87.9     3.90      25.6   13.50  0.1139  0.0572
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0150P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_abs_structure_details 
;
Flack x determined using 544 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_number_reflns         2457
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   0.803
_refine_ls_restrained_S_all      0.803
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.045

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.15228(17) 1.09789(8) 0.77294(8) 0.0476(3) Uani 1 1 d . . . . .
S12 S -0.0332(2) 1.19110(9) 0.93574(9) 0.0706(5) Uani 1 1 d . . . . .
O11 O 0.2545(5) 1.03983(18) 0.71561(19) 0.0619(9) Uani 1 1 d . . . . .
O12 O -0.0557(4) 1.09605(18) 0.76719(18) 0.0561(8) Uani 1 1 d . . . . .
N11 N 0.3700(5) 1.4716(2) 0.6846(2) 0.0542(11) Uani 1 1 d . . . . .
H10 H 0.277466 1.512477 0.674201 0.081 Uiso 1 1 d R U . . .
H11 H 0.494736 1.486947 0.679491 0.081 Uiso 1 1 d R U . . .
N12 N 0.2315(5) 1.0744(2) 0.8620(2) 0.0453(10) Uani 1 1 d . . . . .
N13 N 0.2263(5) 1.0961(3) 1.0058(2) 0.0545(10) Uani 1 1 d . . . . .
C11 C 0.3207(6) 1.3857(3) 0.7081(2) 0.0383(11) Uani 1 1 d . . . . .
C12 C 0.4564(6) 1.3200(3) 0.7214(3) 0.0474(11) Uani 1 1 d . . . . .
H12 H 0.588698 1.335421 0.716975 0.057 Uiso 1 1 calc R U . . .
C13 C 0.4079(6) 1.2329(3) 0.7408(2) 0.0451(13) Uani 1 1 d . . . . .
H13 H 0.505491 1.189111 0.749279 0.054 Uiso 1 1 calc R U . . .
C14 C 0.2181(6) 1.2097(3) 0.7480(2) 0.0371(11) Uani 1 1 d . . . . .
C15 C 0.0781(6) 1.2746(3) 0.7356(3) 0.0481(12) Uani 1 1 d . . . . .
H15 H -0.054051 1.259161 0.741020 0.058 Uiso 1 1 calc R U . . .
C16 C 0.1296(6) 1.3614(3) 0.7155(3) 0.0498(12) Uani 1 1 d . . . . .
H16 H 0.032204 1.405241 0.706549 0.060 Uiso 1 1 calc R U . . .
C17 C 0.1550(6) 1.1141(3) 0.9313(3) 0.0444(11) Uani 1 1 d . . . . .
C18 C 0.1339(8) 1.1442(3) 1.0676(3) 0.0629(14) Uani 1 1 d . . . . .
H18 H 0.168083 1.138784 1.125015 0.076 Uiso 1 1 calc R U . . .
C19 C -0.0047(8) 1.1982(3) 1.0423(3) 0.0698(16) Uani 1 1 d . . . . .
H19 H -0.078528 1.235833 1.078114 0.084 Uiso 1 1 calc R U . . .
N31 N 0.5246(6) 0.9772(3) 1.0030(3) 0.0705(12) Uani 1 1 d . . . . .
H31A H 0.421858 1.014885 1.007302 0.106 Uiso 1 1 calc R U . . .
H31B H 0.569339 0.980989 0.949479 0.106 Uiso 1 1 calc R U . . .
C32 C 0.4592(7) 0.8857(3) 1.0179(3) 0.0637(14) Uani 1 1 d . . . . .
H32A H 0.369045 0.867914 0.972812 0.076 Uiso 1 1 calc R U . . .
H32B H 0.388546 0.883470 1.071717 0.076 Uiso 1 1 calc R U . . .
C33 C 0.6233(9) 0.8203(3) 1.0207(4) 0.0791(17) Uani 1 1 d . . . . .
H33A H 0.574513 0.760898 1.038921 0.095 Uiso 1 1 calc R U . . .
H33B H 0.677027 0.813344 0.963588 0.095 Uiso 1 1 calc R U . . .
C34 C 0.7774(8) 0.8491(4) 1.0778(4) 0.0866(18) Uani 1 1 d . . . . .
H34A H 0.888460 0.807899 1.071835 0.104 Uiso 1 1 calc R U . . .
H34B H 0.730708 0.844862 1.136297 0.104 Uiso 1 1 calc R U . . .
C35 C 0.8428(7) 0.9445(4) 1.0607(4) 0.0891(19) Uani 1 1 d . . . . .
H35A H 0.935811 0.963215 1.104355 0.107 Uiso 1 1 calc R U . . .
H35B H 0.909178 0.946835 1.005822 0.107 Uiso 1 1 calc R U . . .
C36 C 0.6756(8) 1.0086(3) 1.0600(3) 0.0747(16) Uani 1 1 d . . . . .
H36A H 0.622494 1.013998 1.117355 0.090 Uiso 1 1 calc R U . . .
H36B H 0.720268 1.068829 1.042118 0.090 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.445(3) . ?
S11 O12 1.448(3) . ?
S11 N12 1.564(3) . ?
S11 C14 1.770(4) . ?
S12 C19 1.716(5) . ?
S12 C17 1.740(4) . ?
N11 C11 1.375(5) . ?
N11 H10 0.9000 . ?
N11 H11 0.9000 . ?
N12 C17 1.361(5) . ?
N13 C17 1.316(5) . ?
N13 C18 1.377(6) . ?
C11 C12 1.373(5) . ?
C11 C16 1.381(5) . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.368(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(5) . ?
C15 C16 1.378(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.317(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C32 1.453(5) . ?
N31 C36 1.465(5) . ?
N31 H31A 0.9100 . ?
N31 H31B 0.9100 . ?
C32 C33 1.500(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.469(7) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.515(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.502(6) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 116.06(19) . . ?
O11 S11 N12 105.61(19) . . ?
O12 S11 N12 113.85(19) . . ?
O11 S11 C14 106.97(19) . . ?
O12 S11 C14 105.15(19) . . ?
N12 S11 C14 108.87(18) . . ?
C19 S12 C17 89.7(2) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 120.3(3) . . ?
C17 N13 C18 111.5(4) . . ?
C12 C11 N11 122.1(4) . . ?
C12 C11 C16 117.5(4) . . ?
N11 C11 C16 120.4(4) . . ?
C11 C12 C13 122.5(4) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 S11 120.3(3) . . ?
C15 C14 S11 120.3(3) . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N13 C17 N12 119.9(4) . . ?
N13 C17 S12 112.3(3) . . ?
N12 C17 S12 127.8(3) . . ?
C19 C18 N13 116.0(5) . . ?
C19 C18 H18 122.0 . . ?
N13 C18 H18 122.0 . . ?
C18 C19 S12 110.5(4) . . ?
C18 C19 H19 124.7 . . ?
S12 C19 H19 124.7 . . ?
C32 N31 C36 114.8(4) . . ?
C32 N31 H31A 108.6 . . ?
C36 N31 H31A 108.6 . . ?
C32 N31 H31B 108.6 . . ?
C36 N31 H31B 108.6 . . ?
H31A N31 H31B 107.5 . . ?
N31 C32 C33 112.0(4) . . ?
N31 C32 H32A 109.2 . . ?
C33 C32 H32A 109.2 . . ?
N31 C32 H32B 109.2 . . ?
C33 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C34 C33 C32 112.5(4) . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C32 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 C35 112.3(5) . . ?
C33 C34 H34A 109.1 . . ?
C35 C34 H34A 109.1 . . ?
C33 C34 H34B 109.1 . . ?
C35 C34 H34B 109.1 . . ?
H34A C34 H34B 107.9 . . ?
C36 C35 C34 111.3(4) . . ?
C36 C35 H35A 109.4 . . ?
C34 C35 H35A 109.4 . . ?
C36 C35 H35B 109.4 . . ?
C34 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
N31 C36 C35 110.9(4) . . ?
N31 C36 H36A 109.5 . . ?
C35 C36 H36A 109.5 . . ?
N31 C36 H36B 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 -176.0(3) . . . . ?
O12 S11 N12 C17 -47.5(4) . . . . ?
C14 S11 N12 C17 69.4(3) . . . . ?
N11 C11 C12 C13 -176.7(4) . . . . ?
C16 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 -0.1(6) . . . . ?
C12 C13 C14 S11 179.9(3) . . . . ?
O11 S11 C14 C13 -50.6(4) . . . . ?
O12 S11 C14 C13 -174.6(3) . . . . ?
N12 S11 C14 C13 63.1(4) . . . . ?
O11 S11 C14 C15 129.4(3) . . . . ?
O12 S11 C14 C15 5.5(4) . . . . ?
N12 S11 C14 C15 -116.9(3) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
S11 C14 C15 C16 -179.4(3) . . . . ?
C14 C15 C16 C11 -0.6(7) . . . . ?
C12 C11 C16 C15 0.1(6) . . . . ?
N11 C11 C16 C15 177.3(4) . . . . ?
C18 N13 C17 N12 178.4(4) . . . . ?
C18 N13 C17 S12 -0.8(4) . . . . ?
S11 N12 C17 N13 -177.9(3) . . . . ?
S11 N12 C17 S12 1.2(5) . . . . ?
C19 S12 C17 N13 1.2(3) . . . . ?
C19 S12 C17 N12 -178.0(4) . . . . ?
C17 N13 C18 C19 -0.1(6) . . . . ?
N13 C18 C19 S12 1.0(5) . . . . ?
C17 S12 C19 C18 -1.2(4) . . . . ?
C36 N31 C32 C33 -52.4(6) . . . . ?
N31 C32 C33 C34 50.8(6) . . . . ?
C32 C33 C34 C35 -51.7(6) . . . . ?
C33 C34 C35 C36 52.8(7) . . . . ?
C32 N31 C36 C35 53.7(6) . . . . ?
C34 C35 C36 N31 -52.5(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.90 2.19 2.964(4) 143.9 3_556 yes
N11 H11 O11 0.90 2.54 3.221(5) 132.8 3_656 yes
N11 H11 N12 0.90 2.40 3.249(5) 157.9 3_656 yes
N31 H31A N13 0.91 1.82 2.724(5) 173.8 . yes
N31 H31B N11 0.91 2.18 3.082(5) 168.6 3_646 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_63
_database_code_depnum_ccdc_archive 'CCDC 2120814'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 21n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, morpholine (1:1) salt'
_chemical_name_common            'Sulfathiazole, morpholine (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 O2 S2 -, C4 H10 N O +'
_chemical_formula_sum            'C13 H18 N4 O3 S2'
_chemical_formula_weight         342.43
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.592(1)
_cell_length_b                   15.155(3)
_cell_length_c                   15.689(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1567.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6371
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      26.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.357
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6371
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.612
_diffrn_reflns_theta_max         26.252
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3109
_reflns_number_gt                2881
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.989

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  21n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.60      28     33     84.8     3.30     527.0   33.90  0.0183  0.0249
3.60 - 2.37      64     64    100.0     5.23     440.6   42.81  0.0255  0.0243
2.37 - 1.84      91     91    100.0     5.69     244.8   42.03  0.0290  0.0219
1.84 - 1.58      94     94    100.0     5.91     197.0   41.21  0.0328  0.0226
1.58 - 1.43      90     90    100.0     5.21     144.2   36.20  0.0334  0.0252
1.43 - 1.31      96     96    100.0     4.31     146.5   31.76  0.0332  0.0283
1.31 - 1.24      87     87    100.0     4.23     104.8   30.53  0.0366  0.0290
1.24 - 1.17      94     95     98.9     4.02     118.2   28.90  0.0342  0.0312
1.17 - 1.11      94     94    100.0     3.74     107.3   27.48  0.0343  0.0327
1.11 - 1.07      87     87    100.0     3.33      78.7   23.31  0.0408  0.0379
1.07 - 1.03      95     95    100.0     3.00      63.7   21.24  0.0392  0.0405
1.03 - 0.99     106    106    100.0     2.89      52.9   18.83  0.0483  0.0449
0.99 - 0.96      90     90    100.0     2.81      50.2   17.26  0.0547  0.0498
0.96 - 0.93     105    105    100.0     2.65      55.7   16.24  0.0552  0.0529
0.93 - 0.91      83     83    100.0     2.59      39.6   14.17  0.0642  0.0594
0.91 - 0.89      84     85     98.8     2.41      28.9   10.53  0.0793  0.0740
0.89 - 0.87      90     90    100.0     2.57      35.5   12.23  0.0751  0.0697
0.87 - 0.85      97     97    100.0     2.41      31.4   11.17  0.0925  0.0809
0.85 - 0.83     112    112    100.0     2.46      35.9   11.05  0.0927  0.0755
0.83 - 0.82      55     59     93.2     2.07      32.9    9.25  0.1061  0.0843
0.82 - 0.80      98    111     88.3     2.00      25.8    8.23  0.1510  0.1012
#------------------------------------------------------------------------------
0.90 - 0.80     494    512     96.5     2.32      32.1   10.45  0.0978  0.0803
 Inf - 0.80    1840   1864     98.7     3.44     103.4   22.69  0.0351  0.0340
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0142P)²+0.7637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_abs_structure_details 
;
Flack x determined using 1107 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_number_reflns         3109
_refine_ls_number_parameters     217
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.047

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.13457(11) 0.41437(5) 0.27008(5) 0.01888(18) Uani 1 1 d . . . . .
S12 S -0.06064(13) 0.31949(5) 0.43580(5) 0.0287(2) Uani 1 1 d . . . . .
O11 O 0.2399(4) 0.47301(13) 0.21178(14) 0.0266(5) Uani 1 1 d . . . . .
O12 O -0.0857(3) 0.41395(14) 0.26355(14) 0.0250(5) Uani 1 1 d . . . . .
N11 N 0.3831(4) 0.04596(18) 0.18460(18) 0.0234(6) Uani 1 1 d D . . . .
H10 H 0.293(5) 0.007(2) 0.196(2) 0.041(12) Uiso 1 1 d D . . . .
H11 H 0.499(4) 0.031(2) 0.204(2) 0.040(11) Uiso 1 1 d D . . . .
N12 N 0.2141(4) 0.43901(16) 0.36215(16) 0.0211(6) Uani 1 1 d . . . . .
N13 N 0.2140(4) 0.41397(18) 0.50868(16) 0.0234(6) Uani 1 1 d . . . . .
C11 C 0.3264(4) 0.13138(19) 0.20859(18) 0.0179(6) Uani 1 1 d . . . . .
C12 C 0.4719(5) 0.19755(18) 0.21904(18) 0.0202(6) Uani 1 1 d . . . . .
H12 H 0.611636 0.183449 0.213058 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4154(4) 0.28355(19) 0.23801(18) 0.0197(6) Uani 1 1 d . . . . .
H13 H 0.515907 0.327776 0.245719 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2107(5) 0.30463(19) 0.24569(18) 0.0179(6) Uani 1 1 d . . . . .
C15 C 0.0642(5) 0.2395(2) 0.2348(2) 0.0237(7) Uani 1 1 d . . . . .
H15 H -0.075450 0.254026 0.240081 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1209(5) 0.15362(19) 0.2164(2) 0.0233(7) Uani 1 1 d . . . . .
H16 H 0.019901 0.109539 0.209036 0.028 Uiso 1 1 calc R U . . .
C17 C 0.1376(5) 0.39758(17) 0.4322(2) 0.0197(6) Uani 1 1 d . . . . .
C18 C 0.1213(5) 0.3643(2) 0.5714(2) 0.0258(7) Uani 1 1 d . . . . .
H18 H 0.159220 0.368802 0.629633 0.031 Uiso 1 1 calc R U . . .
C19 C -0.0263(6) 0.3092(2) 0.5450(2) 0.0302(8) Uani 1 1 d . . . . .
H19 H -0.100554 0.270352 0.580904 0.036 Uiso 1 1 calc R U . . .
O31 O 0.7604(3) 0.67277(15) 0.57385(15) 0.0293(5) Uani 1 1 d . . . . .
N31 N 0.5234(4) 0.53458(16) 0.50007(17) 0.0227(6) Uani 1 1 d D . . . .
H31A H 0.424(5) 0.488(2) 0.509(2) 0.045(11) Uiso 1 1 d D . . . .
H31B H 0.573(5) 0.531(2) 0.4423(18) 0.044(11) Uiso 1 1 d D . . . .
C32 C 0.4358(5) 0.6238(2) 0.5160(2) 0.0251(7) Uani 1 1 d . . . . .
H32A H 0.366280 0.624375 0.571936 0.030 Uiso 1 1 calc R U . . .
H32B H 0.334502 0.637729 0.471432 0.030 Uiso 1 1 calc R U . . .
C33 C 0.6032(5) 0.6930(2) 0.5153(2) 0.0271(7) Uani 1 1 d . . . . .
H33A H 0.661044 0.697057 0.457145 0.032 Uiso 1 1 calc R U . . .
H33B H 0.544524 0.751221 0.529787 0.032 Uiso 1 1 calc R U . . .
C34 C 0.8490(5) 0.5890(2) 0.5547(2) 0.0306(7) Uani 1 1 d . . . . .
H34A H 0.960446 0.576935 0.595351 0.037 Uiso 1 1 calc R U . . .
H34B H 0.907573 0.590574 0.496588 0.037 Uiso 1 1 calc R U . . .
C35 C 0.6938(5) 0.5155(2) 0.5599(2) 0.0270(7) Uani 1 1 d . . . . .
H35A H 0.757967 0.458567 0.544611 0.032 Uiso 1 1 calc R U . . .
H35B H 0.641329 0.510808 0.618833 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.452(2) . ?
S11 O12 1.455(2) . ?
S11 N12 1.581(3) . ?
S11 C14 1.779(3) . ?
S12 C19 1.735(3) . ?
S12 C17 1.764(3) . ?
N11 C11 1.399(4) . ?
N11 H10 0.86(3) . ?
N11 H11 0.86(3) . ?
N12 C17 1.363(4) . ?
N13 C17 1.324(4) . ?
N13 C18 1.381(4) . ?
C11 C12 1.398(4) . ?
C11 C16 1.401(4) . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(4) . ?
C15 C16 1.385(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.348(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O31 C33 1.419(4) . ?
O31 C34 1.430(4) . ?
N31 C32 1.491(4) . ?
N31 C35 1.492(4) . ?
N31 H31A 0.97(3) . ?
N31 H31B 0.96(3) . ?
C32 C33 1.523(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.515(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 115.81(14) . . ?
O11 S11 N12 105.80(13) . . ?
O12 S11 N12 113.34(14) . . ?
O11 S11 C14 107.56(13) . . ?
O12 S11 C14 105.19(14) . . ?
N12 S11 C14 108.89(13) . . ?
C19 S12 C17 89.72(16) . . ?
C11 N11 H10 114(3) . . ?
C11 N11 H11 113(2) . . ?
H10 N11 H11 111(2) . . ?
C17 N12 S11 120.4(2) . . ?
C17 N13 C18 112.0(3) . . ?
C12 C11 N11 120.8(3) . . ?
C12 C11 C16 118.7(3) . . ?
N11 C11 C16 120.3(3) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 S11 119.6(2) . . ?
C13 C14 S11 120.4(2) . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N13 C17 N12 120.2(3) . . ?
N13 C17 S12 112.3(2) . . ?
N12 C17 S12 127.5(2) . . ?
C19 C18 N13 116.0(3) . . ?
C19 C18 H18 122.0 . . ?
N13 C18 H18 122.0 . . ?
C18 C19 S12 109.9(2) . . ?
C18 C19 H19 125.0 . . ?
S12 C19 H19 125.0 . . ?
C33 O31 C34 110.7(2) . . ?
C32 N31 C35 111.2(2) . . ?
C32 N31 H31A 112(2) . . ?
C35 N31 H31A 106(2) . . ?
C32 N31 H31B 110(2) . . ?
C35 N31 H31B 109(2) . . ?
H31A N31 H31B 109.1(18) . . ?
N31 C32 C33 110.0(3) . . ?
N31 C32 H32A 109.7 . . ?
C33 C32 H32A 109.7 . . ?
N31 C32 H32B 109.7 . . ?
C33 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
O31 C33 C32 112.0(3) . . ?
O31 C33 H33A 109.2 . . ?
C32 C33 H33A 109.2 . . ?
O31 C33 H33B 109.2 . . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
O31 C34 C35 111.5(3) . . ?
O31 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
O31 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
N31 C35 C34 109.4(3) . . ?
N31 C35 H35A 109.8 . . ?
C34 C35 H35A 109.8 . . ?
N31 C35 H35B 109.8 . . ?
C34 C35 H35B 109.8 . . ?
H35A C35 H35B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 177.4(2) . . . . ?
O12 S11 N12 C17 49.5(3) . . . . ?
C14 S11 N12 C17 -67.2(3) . . . . ?
N11 C11 C12 C13 176.3(3) . . . . ?
C16 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C12 C13 C14 S11 179.9(2) . . . . ?
O11 S11 C14 C15 -130.6(2) . . . . ?
O12 S11 C14 C15 -6.6(3) . . . . ?
N12 S11 C14 C15 115.1(2) . . . . ?
O11 S11 C14 C13 49.8(3) . . . . ?
O12 S11 C14 C13 173.8(2) . . . . ?
N12 S11 C14 C13 -64.4(3) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
S11 C14 C15 C16 -179.5(2) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
C12 C11 C16 C15 -0.5(5) . . . . ?
N11 C11 C16 C15 -175.9(3) . . . . ?
C18 N13 C17 N12 -178.4(3) . . . . ?
C18 N13 C17 S12 1.2(3) . . . . ?
S11 N12 C17 N13 175.4(2) . . . . ?
S11 N12 C17 S12 -4.1(4) . . . . ?
C19 S12 C17 N13 -1.7(2) . . . . ?
C19 S12 C17 N12 177.8(3) . . . . ?
C17 N13 C18 C19 0.2(4) . . . . ?
N13 C18 C19 S12 -1.4(4) . . . . ?
C17 S12 C19 C18 1.7(3) . . . . ?
C35 N31 C32 C33 52.7(3) . . . . ?
C34 O31 C33 C32 58.9(3) . . . . ?
N31 C32 C33 O31 -55.1(3) . . . . ?
C33 O31 C34 C35 -60.5(3) . . . . ?
C32 N31 C35 C34 -54.1(3) . . . . ?
O31 C34 C35 N31 57.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.86(3) 2.06(3) 2.917(3) 174(3) 3_545 yes
N11 H11 O11 0.86(3) 2.33(3) 3.169(4) 164(3) 3_645 yes
N11 H11 N12 0.86(3) 2.57(3) 3.196(4) 131(3) 3_645 yes
N31 H31A N13 0.97(3) 1.79(3) 2.742(4) 168(3) . yes
N31 H31B N11 0.96(3) 2.03(3) 2.967(4) 165(3) 3_655 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_41
_database_code_depnum_ccdc_archive 'CCDC 2120819'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 15n
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_41                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Although the intensities appear to be strong, the available data
extend to 1.00 angstrom only. It could be that the data were never measured,
or that the resolution cut-off was applied during processing. The structure is
clearly of limited precision, but remains of value in the context of the set
of structures with which it is published. The coordinates also provide a 
suitable starting set for optimisation by DFT-D methods.
;
_vrf_PLAT029_41                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.739 Why?  
RESPONSE: The data were collected with a point-detector instrument. The data
are effectively complete to about 1.20 angstrom, but the completeness is less
in the range 1.20-1.00 angstrom. The full intensity statistics are included in
the CIF. The structure remains of value in the context of the set
of structures with which it is published. 
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, pyrrolidene-1-carbonitrile (1:1) solvate'
_chemical_name_common            
'Sulfathiazole, pyrrolidene-1-carbonitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C5 H8 N2'
_chemical_formula_sum            'C14 H17 N5 O2 S2'
_chemical_formula_weight         351.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.213(3)
_cell_length_b                   20.550(5)
_cell_length_c                   13.583(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.03(2)
_cell_angle_gamma                90
_cell_volume                     3383.4(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      50.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.999
_shelx_estimated_absorpt_T_min   0.467
_shelx_estimated_absorpt_T_max   0.754
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            2791
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.646
_diffrn_reflns_theta_max         50.640
_diffrn_reflns_theta_full        50.640
_diffrn_measured_fraction_theta_max 0.739
_diffrn_measured_fraction_theta_full 0.739
_diffrn_reflns_Laue_measured_fraction_max 0.739
_diffrn_reflns_Laue_measured_fraction_full 0.739
_diffrn_reflns_point_group_measured_fraction_max 0.739
_diffrn_reflns_point_group_measured_fraction_full 0.739
_reflns_number_total             2642
_reflns_number_gt                1855
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  15n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 4.68      42     43     97.7     1.19      89.3   39.50  0.0161  0.0124
4.68 - 3.05      97     97    100.0     1.13     133.8   40.05  0.0125  0.0127
3.05 - 2.40     139    139    100.0     1.11      47.0   24.94  0.0304  0.0270
2.40 - 2.10     139    139    100.0     1.08      27.2   19.15  0.0345  0.0346
2.10 - 1.90     135    135    100.0     1.07      24.4   16.59  0.0543  0.0403
1.90 - 1.76     135    135    100.0     1.07      25.1   17.68  0.0332  0.0390
1.76 - 1.66     144    144    100.0     1.07      16.0   12.84  0.0379  0.0557
1.66 - 1.57     139    139    100.0     1.06      14.7   13.37  0.0360  0.0583
1.57 - 1.50     140    140    100.0     1.05      14.4   11.99  0.0346  0.0633
1.50 - 1.45     127    127    100.0     1.06      10.8   10.35  0.0860  0.0815
1.45 - 1.39     149    150     99.3     1.05      10.8   10.06  0.0368  0.0844
1.39 - 1.34     159    160     99.4     1.06      11.6   10.03  0.0527  0.0851
1.34 - 1.31     115    116     99.1     1.03       6.4    6.47  0.2562  0.1466
1.31 - 1.27     154    156     98.7     1.04       7.4    7.22  0.0605  0.1272
1.27 - 1.24     126    126    100.0     1.04       8.0    7.22  0.0475  0.1269
1.24 - 1.21     138    144     95.8     1.01       8.5    6.96  0.1019  0.1239
1.21 - 1.18     157    176     89.2     0.91       7.9    6.55  0.1122  0.1401
1.18 - 1.15     134    175     76.6     0.79       7.6    6.28  0.2265  0.1440
1.15 - 1.12     128    191     67.0     0.69       6.8    5.21  0.0612  0.1606
1.12 - 1.08     137    302     45.4     0.45       6.0    5.04  0.0000  0.1991
1.08 - 1.00     123    782     15.7     0.16       5.1    4.42  0.0000  0.2219
#------------------------------------------------------------------------------
1.10 - 1.00     192    940     20.4     0.20       5.2    4.61  0.0000  0.2174
 Inf - 1.00    2757   3716     74.2     0.78      19.4   12.18  0.0308  0.0533
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0832P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2642
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.052

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 1.07011(11) 0.15155(8) 0.99692(13) 0.0530(6) Uani 1 1 d . . . . .
S12 S 0.90542(13) 0.13464(8) 1.17200(13) 0.0651(6) Uani 1 1 d . . . . .
O11 O 1.1453(3) 0.13443(18) 0.9282(3) 0.0684(13) Uani 1 1 d . . . . .
O12 O 1.0991(3) 0.18879(19) 1.0953(3) 0.0676(13) Uani 1 1 d . . . . .
N11 N 0.7254(4) 0.2729(2) 0.7375(4) 0.0625(16) Uani 1 1 d . . . . .
H10 H 0.686772 0.303674 0.758696 0.094 Uiso 1 1 d R U . . .
H11 H 0.710062 0.258594 0.677926 0.094 Uiso 1 1 d R U . . .
N12 N 1.0247(3) 0.0819(2) 1.0255(4) 0.0450(13) Uani 1 1 d . . . . .
N13 N 0.9211(4) 0.0189(2) 1.1163(4) 0.0518(14) Uani 1 1 d . . . . .
H17 H 0.938761 -0.015644 1.086277 0.062 Uiso 1 1 calc R U . . .
C11 C 0.8085(5) 0.2474(3) 0.7967(5) 0.0442(17) Uani 1 1 d . . . . .
C12 C 0.8619(5) 0.1984(3) 0.7509(5) 0.0484(17) Uani 1 1 d . . . . .
H12 H 0.842582 0.185781 0.685318 0.058 Uiso 1 1 calc R U . . .
C13 C 0.9432(5) 0.1715(3) 0.8107(6) 0.0479(18) Uani 1 1 d . . . . .
H13 H 0.982736 0.137641 0.786387 0.057 Uiso 1 1 calc R U . . .
C14 C 0.9746(4) 0.1934(3) 0.9164(5) 0.0447(17) Uani 1 1 d . . . . .
C15 C 0.9240(5) 0.2434(3) 0.9608(5) 0.0447(16) Uani 1 1 d . . . . .
H15 H 0.945144 0.256838 1.025657 0.054 Uiso 1 1 calc R U . . .
C16 C 0.8424(5) 0.2703(3) 0.9020(5) 0.0470(17) Uani 1 1 d . . . . .
H16 H 0.804102 0.304686 0.926203 0.071 Uiso 1 1 calc R U . . .
C17 C 0.9595(5) 0.0773(3) 1.0965(5) 0.0424(16) Uani 1 1 d . . . . .
C18 C 0.8508(5) 0.0177(3) 1.1886(5) 0.065(2) Uani 1 1 d . . . . .
H18 H 0.818964 -0.020126 1.209588 0.078 Uiso 1 1 calc R U . . .
C19 C 0.8336(5) 0.0763(3) 1.2250(5) 0.068(2) Uani 1 1 d . . . . .
H19 H 0.787859 0.084356 1.273536 0.082 Uiso 1 1 calc R U . . .
S21 S 0.58428(11) 0.14628(7) 0.46542(13) 0.0501(5) Uani 1 1 d . . . . .
S22 S 0.49273(13) 0.13997(8) 0.70460(13) 0.0610(6) Uani 1 1 d . . . . .
O21 O 0.6422(3) 0.12299(18) 0.3814(3) 0.0596(12) Uani 1 1 d . . . . .
O22 O 0.6334(3) 0.18539(18) 0.5533(3) 0.0626(12) Uani 1 1 d . . . . .
N21 N 0.2237(4) 0.2790(2) 0.2589(4) 0.0754(17) Uani 1 1 d . . . . .
H20 H 0.191598 0.309331 0.288232 0.113 Uiso 1 1 d R U . . .
H21 H 0.198958 0.267981 0.199212 0.113 Uiso 1 1 d R U . . .
N22 N 0.5396(3) 0.0809(2) 0.5124(4) 0.0445(13) Uani 1 1 d . . . . .
N23 N 0.4621(4) 0.0243(2) 0.6405(4) 0.0485(14) Uani 1 1 d . . . . .
H27 H 0.458574 -0.011088 0.606510 0.073 Uiso 1 1 calc R U . . .
C21 C 0.3101(5) 0.2496(3) 0.3051(5) 0.0463(17) Uani 1 1 d . . . . .
C22 C 0.3549(5) 0.2013(3) 0.2501(5) 0.0528(17) Uani 1 1 d . . . . .
H22 H 0.326418 0.191394 0.185165 0.063 Uiso 1 1 calc R U . . .
C23 C 0.4397(5) 0.1711(3) 0.2966(5) 0.0514(18) Uani 1 1 d . . . . .
H23 H 0.473507 0.137836 0.265112 0.062 Uiso 1 1 calc R U . . .
C24 C 0.4833(4) 0.1899(3) 0.4014(5) 0.0410(16) Uani 1 1 d . . . . .
C25 C 0.4403(5) 0.2397(3) 0.4548(5) 0.0446(16) Uani 1 1 d . . . . .
H25 H 0.469813 0.250747 0.518997 0.054 Uiso 1 1 calc R U . . .
C26 C 0.3556(5) 0.2693(3) 0.4076(5) 0.0482(18) Uani 1 1 d . . . . .
H26 H 0.322896 0.303388 0.438268 0.058 Uiso 1 1 calc R U . . .
C27 C 0.5018(4) 0.0796(3) 0.6069(5) 0.0439(16) Uani 1 1 d . . . . .
C28 C 0.4250(5) 0.0278(4) 0.7390(6) 0.0610(19) Uani 1 1 d . . . . .
H28 H 0.396784 -0.008241 0.768696 0.073 Uiso 1 1 calc R U . . .
C29 C 0.4343(5) 0.0864(4) 0.7840(5) 0.069(2) Uani 1 1 d . . . . .
H29 H 0.413572 0.096577 0.845800 0.083 Uiso 1 1 calc R U . . .
N30 N 0.6698(5) 0.0524(3) 0.9519(5) 0.085(2) Uani 1 1 d . . . . .
N31 N 0.5611(5) 0.1021(4) 1.0744(6) 0.102(2) Uani 1 1 d . . . . .
C30 C 0.7776(7) 0.0391(4) 0.8210(7) 0.114(3) Uani 1 1 d . . . . .
H30A H 0.771108 0.054387 0.752963 0.137 Uiso 1 1 calc R U . . .
H30B H 0.855099 0.031915 0.843453 0.137 Uiso 1 1 calc R U . . .
C31 C 0.7318(5) 0.0905(3) 0.8862(5) 0.069(2) Uani 1 1 d . . . . .
H31A H 0.790963 0.114664 0.923885 0.083 Uiso 1 1 calc R U . . .
H31B H 0.683898 0.120676 0.846452 0.083 Uiso 1 1 calc R U . . .
C32 C 0.6699(6) -0.0167(4) 0.9268(7) 0.098(3) Uani 1 1 d . . . . .
H32A H 0.595630 -0.034158 0.920283 0.117 Uiso 1 1 calc R U . . .
H32B H 0.715471 -0.041056 0.977545 0.117 Uiso 1 1 calc R U . . .
C33 C 0.7187(6) -0.0202(4) 0.8254(7) 0.109(3) Uani 1 1 d . . . . .
H33A H 0.767565 -0.057301 0.823874 0.130 Uiso 1 1 calc R U . . .
H33B H 0.660220 -0.023570 0.770487 0.130 Uiso 1 1 calc R U . . .
C34 C 0.6126(6) 0.0792(4) 1.0173(7) 0.074(2) Uani 1 1 d . . . . .
N40 N 0.1374(6) 0.0370(4) 0.4258(7) 0.113(3) Uani 1 1 d . . . . .
N41 N 0.0401(9) -0.0635(5) 0.3921(10) 0.232(7) Uani 1 1 d . . . . .
C40 C 0.1542(8) 0.1437(4) 0.4780(10) 0.160(5) Uani 1 1 d . . . . .
H40A H 0.174335 0.185577 0.452765 0.193 Uiso 1 1 calc R U . . .
H40B H 0.107925 0.150465 0.530306 0.193 Uiso 1 1 calc R U . . .
C41 C 0.0959(7) 0.1014(7) 0.3953(8) 0.141(4) Uani 1 1 d . . . . .
H41A H 0.016352 0.103814 0.393137 0.169 Uiso 1 1 calc R U . . .
H41B H 0.116705 0.113425 0.331035 0.169 Uiso 1 1 calc R U . . .
C42 C 0.2191(7) 0.0396(5) 0.5085(8) 0.126(3) Uani 1 1 d . . . . .
H42A H 0.282882 0.013442 0.498322 0.151 Uiso 1 1 calc R U . . .
H42B H 0.190645 0.025602 0.568633 0.151 Uiso 1 1 calc R U . . .
C43 C 0.2450(7) 0.1083(5) 0.5111(8) 0.134(4) Uani 1 1 d . . . . .
H43A H 0.271686 0.121118 0.578554 0.161 Uiso 1 1 calc R U . . .
H43B H 0.302815 0.116916 0.469909 0.161 Uiso 1 1 calc R U . . .
C44 C 0.0835(9) -0.0171(7) 0.4091(9) 0.157(5) Uani 1 1 d . . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.430(4) . ?
S11 O12 1.543(4) . ?
S11 N12 1.599(5) . ?
S11 C14 1.727(6) . ?
S12 C19 1.697(6) . ?
S12 C17 1.744(6) . ?
N11 C11 1.323(7) . ?
N11 H10 0.8601 . ?
N11 H11 0.8601 . ?
N12 C17 1.327(7) . ?
N13 C17 1.327(6) . ?
N13 C18 1.381(7) . ?
N13 H17 0.8600 . ?
C11 C12 1.388(7) . ?
C11 C16 1.513(8) . ?
C12 C13 1.324(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.509(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(7) . ?
C15 C16 1.320(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.328(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
S21 O21 1.493(4) . ?
S21 O22 1.502(4) . ?
S21 N22 1.610(5) . ?
S21 C24 1.679(6) . ?
S22 C29 1.752(7) . ?
S22 C27 1.830(6) . ?
N21 C21 1.308(7) . ?
N21 H20 0.8600 . ?
N21 H21 0.8600 . ?
N22 C27 1.417(7) . ?
N23 C27 1.337(7) . ?
N23 C28 1.465(7) . ?
N23 H27 0.8600 . ?
C21 C22 1.393(8) . ?
C21 C26 1.491(8) . ?
C22 C23 1.303(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.507(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.392(7) . ?
C25 C26 1.300(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C28 C29 1.350(8) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
N30 C34 1.316(10) . ?
N30 C32 1.460(8) . ?
N30 C31 1.466(8) . ?
N31 C34 1.157(9) . ?
C30 C33 1.421(9) . ?
C30 C31 1.527(9) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.567(10) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
N40 C44 1.299(12) . ?
N40 C42 1.409(10) . ?
N40 C41 1.458(10) . ?
N41 C44 1.102(11) . ?
C40 C43 1.355(10) . ?
C40 C41 1.526(12) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.447(10) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 126.1(2) . . ?
O11 S11 N12 102.0(2) . . ?
O12 S11 N12 106.5(2) . . ?
O11 S11 C14 98.4(3) . . ?
O12 S11 C14 111.6(3) . . ?
N12 S11 C14 111.8(2) . . ?
C19 S12 C17 91.4(3) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 119.8(4) . . ?
C17 N13 C18 115.2(5) . . ?
C17 N13 H17 122.4 . . ?
C18 N13 H17 122.4 . . ?
N11 C11 C12 112.4(6) . . ?
N11 C11 C16 123.5(6) . . ?
C12 C11 C16 124.1(6) . . ?
C13 C12 C11 112.7(6) . . ?
C13 C12 H12 123.7 . . ?
C11 C12 H12 123.7 . . ?
C12 C13 C14 122.9(5) . . ?
C12 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C15 C14 C13 124.3(5) . . ?
C15 C14 S11 113.5(6) . . ?
C13 C14 S11 121.9(5) . . ?
C16 C15 C14 113.2(6) . . ?
C16 C15 H15 123.4 . . ?
C14 C15 H15 123.4 . . ?
C15 C16 C11 122.7(6) . . ?
C15 C16 H16 118.7 . . ?
C11 C16 H16 118.7 . . ?
N13 C17 N12 118.1(5) . . ?
N13 C17 S12 108.8(5) . . ?
N12 C17 S12 133.1(5) . . ?
C19 C18 N13 112.9(6) . . ?
C19 C18 H18 123.6 . . ?
N13 C18 H18 123.6 . . ?
C18 C19 S12 111.7(5) . . ?
C18 C19 H19 124.2 . . ?
S12 C19 H19 124.2 . . ?
O21 S21 O22 126.8(2) . . ?
O21 S21 N22 104.5(2) . . ?
O22 S21 N22 104.7(3) . . ?
O21 S21 C24 99.3(3) . . ?
O22 S21 C24 108.8(3) . . ?
N22 S21 C24 112.8(2) . . ?
C29 S22 C27 94.9(3) . . ?
C21 N21 H20 120.0 . . ?
C21 N21 H21 120.0 . . ?
H20 N21 H21 120.0 . . ?
C27 N22 S21 122.6(4) . . ?
C27 N23 C28 115.8(5) . . ?
C27 N23 H27 122.1 . . ?
C28 N23 H27 122.1 . . ?
N21 C21 C22 114.7(7) . . ?
N21 C21 C26 120.6(6) . . ?
C22 C21 C26 124.6(6) . . ?
C23 C22 C21 114.8(6) . . ?
C23 C22 H22 122.6 . . ?
C21 C22 H22 122.6 . . ?
C22 C23 C24 120.3(6) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 124.6(5) . . ?
C25 C24 S21 115.0(5) . . ?
C23 C24 S21 120.3(5) . . ?
C26 C25 C24 114.5(6) . . ?
C26 C25 H25 122.8 . . ?
C24 C25 H25 122.8 . . ?
C25 C26 C21 121.1(6) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
N23 C27 N22 119.9(5) . . ?
N23 C27 S22 105.8(5) . . ?
N22 C27 S22 134.4(5) . . ?
C29 C28 N23 116.0(6) . . ?
C29 C28 H28 122.0 . . ?
N23 C28 H28 122.0 . . ?
C28 C29 S22 107.4(5) . . ?
C28 C29 H29 126.3 . . ?
S22 C29 H29 126.3 . . ?
C34 N30 C32 125.5(6) . . ?
C34 N30 C31 123.0(6) . . ?
C32 N30 C31 111.2(6) . . ?
C33 C30 C31 110.2(6) . . ?
C33 C30 H30A 109.6 . . ?
C31 C30 H30A 109.6 . . ?
C33 C30 H30B 109.6 . . ?
C31 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
N30 C31 C30 103.7(5) . . ?
N30 C31 H31A 111.0 . . ?
C30 C31 H31A 111.0 . . ?
N30 C31 H31B 111.0 . . ?
C30 C31 H31B 111.0 . . ?
H31A C31 H31B 109.0 . . ?
N30 C32 C33 105.2(6) . . ?
N30 C32 H32A 110.7 . . ?
C33 C32 H32A 110.7 . . ?
N30 C32 H32B 110.7 . . ?
C33 C32 H32B 110.7 . . ?
H32A C32 H32B 108.8 . . ?
C30 C33 C32 104.2(6) . . ?
C30 C33 H33A 110.9 . . ?
C32 C33 H33A 110.9 . . ?
C30 C33 H33B 110.9 . . ?
C32 C33 H33B 110.9 . . ?
H33A C33 H33B 108.9 . . ?
N31 C34 N30 179.0(8) . . ?
C44 N40 C42 117.8(11) . . ?
C44 N40 C41 125.2(10) . . ?
C42 N40 C41 112.3(7) . . ?
C43 C40 C41 103.2(9) . . ?
C43 C40 H40A 111.1 . . ?
C41 C40 H40A 111.1 . . ?
C43 C40 H40B 111.1 . . ?
C41 C40 H40B 111.1 . . ?
H40A C40 H40B 109.1 . . ?
N40 C41 C40 101.1(7) . . ?
N40 C41 H41A 111.6 . . ?
C40 C41 H41A 111.6 . . ?
N40 C41 H41B 111.6 . . ?
C40 C41 H41B 111.6 . . ?
H41A C41 H41B 109.4 . . ?
N40 C42 C43 100.8(8) . . ?
N40 C42 H42A 111.6 . . ?
C43 C42 H42A 111.6 . . ?
N40 C42 H42B 111.6 . . ?
C43 C42 H42B 111.6 . . ?
H42A C42 H42B 109.4 . . ?
C40 C43 C42 110.3(8) . . ?
C40 C43 H43A 109.6 . . ?
C42 C43 H43A 109.6 . . ?
C40 C43 H43B 109.6 . . ?
C42 C43 H43B 109.6 . . ?
H43A C43 H43B 108.1 . . ?
N41 C44 N40 177.4(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 173.4(4) . . . . ?
O12 S11 N12 C17 39.7(4) . . . . ?
C14 S11 N12 C17 -82.3(5) . . . . ?
N11 C11 C12 C13 -178.3(5) . . . . ?
C16 C11 C12 C13 2.8(8) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
C12 C13 C14 C15 -1.0(8) . . . . ?
C12 C13 C14 S11 172.4(4) . . . . ?
O11 S11 C14 C15 -148.1(4) . . . . ?
O12 S11 C14 C15 -13.7(5) . . . . ?
N12 S11 C14 C15 105.4(4) . . . . ?
O11 S11 C14 C13 37.9(5) . . . . ?
O12 S11 C14 C13 172.3(4) . . . . ?
N12 S11 C14 C13 -68.6(5) . . . . ?
C13 C14 C15 C16 1.2(8) . . . . ?
S11 C14 C15 C16 -172.6(4) . . . . ?
C14 C15 C16 C11 0.4(8) . . . . ?
N11 C11 C16 C15 178.5(5) . . . . ?
C12 C11 C16 C15 -2.7(8) . . . . ?
C18 N13 C17 N12 -177.9(5) . . . . ?
C18 N13 C17 S12 0.0(6) . . . . ?
S11 N12 C17 N13 178.2(4) . . . . ?
S11 N12 C17 S12 0.9(7) . . . . ?
C19 S12 C17 N13 -0.4(4) . . . . ?
C19 S12 C17 N12 177.1(6) . . . . ?
C17 N13 C18 C19 0.5(8) . . . . ?
N13 C18 C19 S12 -0.8(7) . . . . ?
C17 S12 C19 C18 0.7(5) . . . . ?
O21 S21 N22 C27 165.3(4) . . . . ?
O22 S21 N22 C27 30.3(4) . . . . ?
C24 S21 N22 C27 -87.8(5) . . . . ?
N21 C21 C22 C23 -178.8(5) . . . . ?
C26 C21 C22 C23 2.9(8) . . . . ?
C21 C22 C23 C24 -0.9(8) . . . . ?
C22 C23 C24 C25 -1.2(8) . . . . ?
C22 C23 C24 S21 173.8(4) . . . . ?
O21 S21 C24 C25 -154.7(4) . . . . ?
O22 S21 C24 C25 -20.6(5) . . . . ?
N22 S21 C24 C25 95.1(4) . . . . ?
O21 S21 C24 C23 29.8(4) . . . . ?
O22 S21 C24 C23 164.0(4) . . . . ?
N22 S21 C24 C23 -80.4(5) . . . . ?
C23 C24 C25 C26 1.2(8) . . . . ?
S21 C24 C25 C26 -174.0(4) . . . . ?
C24 C25 C26 C21 0.7(8) . . . . ?
N21 C21 C26 C25 178.8(5) . . . . ?
C22 C21 C26 C25 -2.9(9) . . . . ?
C28 N23 C27 N22 180.0(4) . . . . ?
C28 N23 C27 S22 0.2(5) . . . . ?
S21 N22 C27 N23 177.7(4) . . . . ?
S21 N22 C27 S22 -2.6(7) . . . . ?
C29 S22 C27 N23 -0.6(4) . . . . ?
C29 S22 C27 N22 179.6(5) . . . . ?
C27 N23 C28 C29 0.5(7) . . . . ?
N23 C28 C29 S22 -0.9(7) . . . . ?
C27 S22 C29 C28 0.9(5) . . . . ?
C34 N30 C31 C30 -176.8(7) . . . . ?
C32 N30 C31 C30 -3.4(8) . . . . ?
C33 C30 C31 N30 17.8(9) . . . . ?
C34 N30 C32 C33 162.8(7) . . . . ?
C31 N30 C32 C33 -10.4(8) . . . . ?
C31 C30 C33 C32 -23.9(9) . . . . ?
N30 C32 C33 C30 20.9(8) . . . . ?
C44 N40 C41 C40 148.8(10) . . . . ?
C42 N40 C41 C40 -6.1(10) . . . . ?
C43 C40 C41 N40 25.0(11) . . . . ?
C44 N40 C42 C43 -170.7(8) . . . . ?
C41 N40 C42 C43 -13.7(10) . . . . ?
C41 C40 C43 C42 -36.5(13) . . . . ?
N40 C42 C43 C40 32.1(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O21 0.86 2.36 3.149(6) 152.9 4_566 yes
N11 H11 O22 0.86 2.37 3.173(6) 155.5 . yes
N13 H17 O11 0.86 2.65 3.292(6) 132.9 3_757 yes
N13 H17 N12 0.86 2.13 2.959(7) 162.6 3_757 yes
N21 H20 O11 0.86 2.35 3.149(7) 154.0 4_465 yes
N21 H21 O12 0.86 2.39 3.140(7) 146.2 1_454 yes
N23 H27 O21 0.86 2.62 3.283(6) 134.5 3_656 yes
N23 H27 N22 0.86 2.16 2.996(7) 163.4 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_66
_database_code_depnum_ccdc_archive 'CCDC 2120816'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 24n
#===============================================================================
# start Validation Reply Form
_vrf_PLAT029_66                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.817 Why?  
RESPONSE: These are the data that are available. The missing data are
distributed evenly through reciprocal space, except for a rapid drop-off in
the shell 0.94-0.84 angstrom (overall shell completeness ca 50%). The structure
is clear and there is no adverse effect on the refinement.
;
# end Validation Reply Form
#===============================================================================


_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, cyclohexylamine (1:1) salt'
_chemical_name_common            'Sulfathiazole, cyclohexylamine (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 S2 O2 -, C6 H14 N +'
_chemical_formula_sum            'C15 H22 N4 O2 S2'
_chemical_formula_weight         354.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.081(2)
_cell_length_b                   16.676(2)
_cell_length_c                   13.1690(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.56(2)
_cell_angle_gamma                90
_cell_volume                     1717.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6680
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      24.93

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.325
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'FAST TV area detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6680
_diffrn_reflns_av_unetI/netI     0.1118
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.571
_diffrn_reflns_theta_max         24.932
_diffrn_reflns_theta_full        24.932
_diffrn_measured_fraction_theta_max 0.817
_diffrn_measured_fraction_theta_full 0.817
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_Laue_measured_fraction_full 0.817
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_point_group_measured_fraction_full 0.817
_reflns_number_total             2450
_reflns_number_gt                1720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  24n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.75      38     43     88.4     3.42     366.4   89.72  0.1413  0.0073
3.75 - 2.49      88     94     93.6     3.09     153.1   46.75  0.1488  0.0147
2.49 - 1.95     126    131     96.2     3.24      88.9   32.49  0.1165  0.0219
1.95 - 1.69     130    134     97.0     3.19      57.7   23.77  0.0917  0.0325
1.69 - 1.54     124    126     98.4     3.12      36.5   16.43  0.0527  0.0500
1.54 - 1.43     129    131     98.5     3.13      33.5   14.61  0.0582  0.0531
1.43 - 1.34     131    135     97.0     2.90      30.4   12.16  0.0554  0.0600
1.34 - 1.28     119    121     98.3     3.00      24.7   11.23  0.0462  0.0717
1.28 - 1.22     137    139     98.6     2.90      28.1   10.15  0.0520  0.0732
1.22 - 1.17     124    129     96.1     2.75      25.0    9.04  0.0363  0.0837
1.17 - 1.13     119    130     91.5     2.70      19.1    7.83  0.0492  0.1059
1.13 - 1.09     145    155     93.5     2.49      18.2    6.77  0.0478  0.1159
1.09 - 1.06     105    119     88.2     2.41      15.2    6.23  0.0520  0.1352
1.06 - 1.03     120    137     87.6     2.26      11.2    4.62  0.0649  0.1762
1.03 - 1.00     147    164     89.6     2.21      10.1    4.15  0.0629  0.2015
1.00 - 0.97     153    176     86.9     2.10       8.4    3.60  0.0787  0.2411
0.97 - 0.95     118    134     88.1     1.98       7.3    3.00  0.0816  0.2812
0.95 - 0.93     112    142     78.9     1.79       8.0    3.21  0.0709  0.2640
0.93 - 0.91     117    149     78.5     1.59       6.2    2.59  0.0835  0.3530
0.91 - 0.88     137    264     51.9     0.89       6.0    2.33  0.0806  0.3739
0.88 - 0.85      89    297     30.0     0.43       5.0    1.76  0.1009  0.4682
0.85 - 0.84       9     75     12.0     0.13       8.6    2.03  0.2833  0.3600
#------------------------------------------------------------------------------
0.94 - 0.84     406    853     47.6     0.85       6.0    2.36  0.0833  0.3725
 Inf - 0.84    2517   3125     80.5     2.17      33.1   11.87  0.0952  0.0614
#================================================================================
;

_computing_data_collection       'MADNES (Pflugarth & Messerschmidt, 1989)'
_computing_cell_refinement       'FIND (MADNES reference manual ver. 2.4, 1993)'
_computing_data_reduction        'ABSURD (Pflugarth & Messerschmidt, 1989)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2450
_refine_ls_number_parameters     218
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.069

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.27725(9) 0.95170(4) 0.82278(6) 0.0381(2) Uani 1 1 d . . . . .
S12 S -0.02401(10) 1.01305(5) 0.63119(7) 0.0543(3) Uani 1 1 d . . . . .
O11 O 0.3867(2) 0.93530(12) 0.92644(16) 0.0484(6) Uani 1 1 d . . . . .
O12 O 0.3404(2) 1.01073(11) 0.76178(17) 0.0521(6) Uani 1 1 d . . . . .
N11 N 0.2410(3) 0.64343(16) 0.5960(2) 0.0572(8) Uani 1 1 d D . . . .
H10 H 0.310(4) 0.6322(18) 0.546(3) 0.114(15) Uiso 1 1 d D . . . .
H11 H 0.223(4) 0.5937(17) 0.632(2) 0.087(12) Uiso 1 1 d D . . . .
N12 N 0.0972(3) 0.97396(12) 0.84264(18) 0.0360(6) Uani 1 1 d . . . . .
N13 N -0.1909(3) 0.99724(13) 0.7716(2) 0.0406(6) Uani 1 1 d . . . . .
C11 C 0.2494(3) 0.71525(17) 0.6480(2) 0.0391(7) Uani 1 1 d . . . . .
C12 C 0.1905(3) 0.72190(17) 0.7388(3) 0.0440(8) Uani 1 1 d . . . . .
H12 H 0.147317 0.675741 0.765777 0.053 Uiso 1 1 calc R U . . .
C13 C 0.1939(3) 0.79359(17) 0.7894(2) 0.0408(8) Uani 1 1 d . . . . .
H13 H 0.152984 0.796833 0.850877 0.049 Uiso 1 1 calc R U . . .
C14 C 0.2567(3) 0.86161(16) 0.7516(2) 0.0324(7) Uani 1 1 d . . . . .
C15 C 0.3124(3) 0.85552(17) 0.6617(2) 0.0424(8) Uani 1 1 d . . . . .
H15 H 0.354861 0.901926 0.634823 0.051 Uiso 1 1 calc R U . . .
C16 C 0.3083(3) 0.78411(18) 0.6098(2) 0.0437(8) Uani 1 1 d . . . . .
H16 H 0.346029 0.781772 0.547120 0.052 Uiso 1 1 calc R U . . .
C17 C -0.0353(4) 0.99239(14) 0.7598(2) 0.0334(7) Uani 1 1 d . . . . .
C18 C -0.3047(4) 1.01697(17) 0.6783(3) 0.0496(9) Uani 1 1 d . . . . .
H18 H -0.423199 1.023612 0.673595 0.059 Uiso 1 1 calc R U . . .
C19 C -0.2415(4) 1.02627(18) 0.5954(3) 0.0545(9) Uani 1 1 d . . . . .
H19 H -0.306901 1.038441 0.526532 0.065 Uiso 1 1 calc R U . . .
N31 N 0.7565(3) 0.92630(12) 0.95985(19) 0.0396(6) Uani 1 1 d . . . . .
H31A H 0.776308 0.948813 0.901064 0.059 Uiso 1 1 calc R U . . .
H31B H 0.822947 0.950767 1.017621 0.059 Uiso 1 1 calc R U . . .
H31C H 0.644381 0.932501 0.959243 0.059 Uiso 1 1 calc R U . . .
C30 C 0.7992(3) 0.83856(16) 0.9625(2) 0.0396(7) Uani 1 1 d . . . . .
H30A H 0.926199 0.832952 0.976801 0.047 Uiso 1 1 calc R U . . .
C32 C 0.7202(4) 0.80128(18) 0.8582(2) 0.0524(9) Uani 1 1 d . . . . .
H32A H 0.768162 0.826542 0.803825 0.063 Uiso 1 1 calc R U . . .
H32B H 0.595354 0.811075 0.839493 0.063 Uiso 1 1 calc R U . . .
C33 C 0.7536(5) 0.71167(19) 0.8604(3) 0.0685(10) Uani 1 1 d . . . . .
H33A H 0.693471 0.687992 0.792173 0.082 Uiso 1 1 calc R U . . .
H33B H 0.877644 0.702086 0.870646 0.082 Uiso 1 1 calc R U . . .
C34 C 0.6938(4) 0.67114(19) 0.9471(3) 0.0609(10) Uani 1 1 d . . . . .
H34A H 0.567865 0.675420 0.932624 0.073 Uiso 1 1 calc R U . . .
H34B H 0.723951 0.613516 0.949083 0.073 Uiso 1 1 calc R U . . .
C35 C 0.7738(4) 0.7084(2) 1.0514(3) 0.0658(10) Uani 1 1 d . . . . .
H35A H 0.898490 0.698311 1.069784 0.079 Uiso 1 1 calc R U . . .
H35B H 0.726022 0.683174 1.105887 0.079 Uiso 1 1 calc R U . . .
C36 C 0.7416(4) 0.79825(18) 1.0500(3) 0.0544(9) Uani 1 1 d . . . . .
H36A H 0.618021 0.808222 1.041124 0.065 Uiso 1 1 calc R U . . .
H36B H 0.803846 0.821660 1.117984 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.443(2) . ?
S11 O11 1.454(2) . ?
S11 N12 1.586(2) . ?
S11 C14 1.756(3) . ?
S12 C19 1.716(3) . ?
S12 C17 1.753(3) . ?
N11 C11 1.372(4) . ?
N11 H10 0.98(2) . ?
N11 H11 0.98(2) . ?
N12 C17 1.358(3) . ?
N13 C17 1.308(3) . ?
N13 C18 1.377(4) . ?
C11 C16 1.385(4) . ?
C11 C12 1.399(4) . ?
C12 C13 1.366(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(4) . ?
C15 C16 1.369(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.326(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C30 1.502(3) . ?
N31 H31A 0.9100 . ?
N31 H31B 0.9100 . ?
N31 H31C 0.9100 . ?
C30 C32 1.497(4) . ?
C30 C36 1.505(4) . ?
C30 H30A 1.0000 . ?
C32 C33 1.517(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.507(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.498(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.520(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 115.75(12) . . ?
O12 S11 N12 113.57(12) . . ?
O11 S11 N12 104.82(12) . . ?
O12 S11 C14 106.62(13) . . ?
O11 S11 C14 107.08(12) . . ?
N12 S11 C14 108.69(12) . . ?
C19 S12 C17 89.54(15) . . ?
C11 N11 H10 122(2) . . ?
C11 N11 H11 119.4(19) . . ?
H10 N11 H11 109.9(14) . . ?
C17 N12 S11 119.4(2) . . ?
C17 N13 C18 110.8(3) . . ?
N11 C11 C16 121.4(3) . . ?
N11 C11 C12 120.7(3) . . ?
C16 C11 C12 117.8(3) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 S11 121.1(2) . . ?
C13 C14 S11 120.2(2) . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N13 C17 N12 120.4(3) . . ?
N13 C17 S12 112.8(2) . . ?
N12 C17 S12 126.8(2) . . ?
C19 C18 N13 117.0(3) . . ?
C19 C18 H18 121.5 . . ?
N13 C18 H18 121.5 . . ?
C18 C19 S12 109.8(3) . . ?
C18 C19 H19 125.1 . . ?
S12 C19 H19 125.1 . . ?
C30 N31 H31A 109.5 . . ?
C30 N31 H31B 109.5 . . ?
H31A N31 H31B 109.5 . . ?
C30 N31 H31C 109.5 . . ?
H31A N31 H31C 109.5 . . ?
H31B N31 H31C 109.5 . . ?
C32 C30 N31 109.9(2) . . ?
C32 C30 C36 112.0(3) . . ?
N31 C30 C36 109.9(2) . . ?
C32 C30 H30A 108.3 . . ?
N31 C30 H30A 108.3 . . ?
C36 C30 H30A 108.3 . . ?
C30 C32 C33 111.0(3) . . ?
C30 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
C30 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C34 C33 C32 111.5(3) . . ?
C34 C33 H33A 109.3 . . ?
C32 C33 H33A 109.3 . . ?
C34 C33 H33B 109.3 . . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?
C35 C34 C33 111.2(3) . . ?
C35 C34 H34A 109.4 . . ?
C33 C34 H34A 109.4 . . ?
C35 C34 H34B 109.4 . . ?
C33 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C34 C35 C36 111.4(3) . . ?
C34 C35 H35A 109.3 . . ?
C36 C35 H35A 109.3 . . ?
C34 C35 H35B 109.3 . . ?
C36 C35 H35B 109.3 . . ?
H35A C35 H35B 108.0 . . ?
C30 C36 C35 111.4(3) . . ?
C30 C36 H36A 109.4 . . ?
C35 C36 H36A 109.4 . . ?
C30 C36 H36B 109.4 . . ?
C35 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 53.0(2) . . . . ?
O11 S11 N12 C17 -179.71(19) . . . . ?
C14 S11 N12 C17 -65.5(2) . . . . ?
N11 C11 C12 C13 -178.2(3) . . . . ?
C16 C11 C12 C13 -1.2(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C12 C13 C14 S11 -174.7(2) . . . . ?
O12 S11 C14 C15 6.0(3) . . . . ?
O11 S11 C14 C15 -118.5(2) . . . . ?
N12 S11 C14 C15 128.8(2) . . . . ?
O12 S11 C14 C13 -178.4(2) . . . . ?
O11 S11 C14 C13 57.2(2) . . . . ?
N12 S11 C14 C13 -55.6(3) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
S11 C14 C15 C16 175.2(2) . . . . ?
C14 C15 C16 C11 -1.0(4) . . . . ?
N11 C11 C16 C15 178.7(3) . . . . ?
C12 C11 C16 C15 1.8(4) . . . . ?
C18 N13 C17 N12 179.6(2) . . . . ?
C18 N13 C17 S12 0.4(3) . . . . ?
S11 N12 C17 N13 168.09(19) . . . . ?
S11 N12 C17 S12 -12.8(3) . . . . ?
C19 S12 C17 N13 -1.2(2) . . . . ?
C19 S12 C17 N12 179.7(2) . . . . ?
C17 N13 C18 C19 0.9(4) . . . . ?
N13 C18 C19 S12 -1.7(4) . . . . ?
C17 S12 C19 C18 1.6(2) . . . . ?
N31 C30 C32 C33 -177.0(2) . . . . ?
C36 C30 C32 C33 -54.7(3) . . . . ?
C30 C32 C33 C34 55.1(4) . . . . ?
C32 C33 C34 C35 -55.6(4) . . . . ?
C33 C34 C35 C36 55.1(4) . . . . ?
C32 C30 C36 C35 54.4(4) . . . . ?
N31 C30 C36 C35 176.8(3) . . . . ?
C34 C35 C36 C30 -54.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.98(2) 2.15(3) 3.069(3) 155(3) 4_575 yes
N11 H11 N13 0.98(2) 2.11(2) 3.082(4) 172(3) 2_546 yes
N31 H31A N13 0.91 1.96 2.873(3) 177.7 1_655 yes
N31 H31B S11 0.91 2.93 3.578(2) 129.6 3_677 yes
N31 H31B N12 0.91 2.19 3.063(3) 161.5 3_677 yes
N31 H31C O11 0.91 2.02 2.913(3) 167.4 . yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_60
_database_code_depnum_ccdc_archive 'CCDC 2120818'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 17n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, N-methylpyrrolidine (1:1) salt'
_chemical_name_common            'Sulfathiazole, N-methylpyrrolidine (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 O2 S2 -, C5 H12 N +'
_chemical_formula_sum            'C14 H20 N4 O2 S2'
_chemical_formula_weight         340.46
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.943(3)
_cell_length_b                   9.260(2)
_cell_length_c                   12.698(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1639.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4499
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      30.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.337
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4499
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.658
_diffrn_reflns_theta_max         30.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4499
_reflns_number_gt                3762
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_max     0.942
_reflns_Friedel_fraction_full    0.984

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  17n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.12      41     47     87.2     1.17     372.3   48.44  0.0045  0.0172
3.12 - 2.07      92     92    100.0     1.52     165.0   43.75  0.0110  0.0165
2.07 - 1.61     133    133    100.0     1.63      87.5   38.92  0.0113  0.0191
1.61 - 1.39     135    135    100.0     1.66      60.8   32.51  0.0167  0.0231
1.39 - 1.26     136    136    100.0     1.72      45.6   29.91  0.0186  0.0249
1.26 - 1.16     133    133    100.0     1.75      43.3   29.21  0.0239  0.0283
1.16 - 1.09     135    135    100.0     1.72      40.6   23.45  0.0228  0.0306
1.09 - 1.03     145    145    100.0     1.77      23.9   17.88  0.0349  0.0420
1.03 - 0.98     120    134     89.6     1.61      28.5   20.57  0.0311  0.0373
0.98 - 0.93     149    173     86.1     1.57      21.5   16.75  0.0415  0.0454
0.93 - 0.89     138    178     77.5     1.38      22.3   16.56  0.0383  0.0446
0.89 - 0.86     105    144     72.9     1.35      15.9   12.79  0.0565  0.0578
0.86 - 0.82     156    230     67.8     1.23      16.6   13.55  0.0508  0.0581
0.82 - 0.79     129    209     61.7     1.14      12.7   11.14  0.0628  0.0700
0.79 - 0.76     132    230     57.4     1.04      15.9   12.00  0.0568  0.0647
0.76 - 0.73     142    270     52.6     0.96      12.8    9.99  0.0733  0.0797
0.73 - 0.70     150    324     46.3     0.85      10.8    8.00  0.0940  0.1027
0.70 - 0.68     102    258     39.5     0.72       9.0    6.72  0.1246  0.1245
0.68 - 0.65     143    426     33.6     0.62       9.8    6.80  0.1250  0.1265
0.65 - 0.62     118    518     22.8     0.42       8.0    5.69  0.1448  0.1548
0.62 - 0.55     126   1675      7.5     0.14       8.3    5.35  0.1643  0.1650
0.55 - 0.54       8    479      1.7     0.02       3.2    2.42  0.4106  0.5236
#------------------------------------------------------------------------------
0.64 - 0.54     207   2504      8.3     0.15       7.8    5.30  0.1577  0.1693
 Inf - 0.54    2668   6204     43.0     0.76      36.2   18.24  0.0325  0.0351
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          'Refined as a 2-component inversion twin.'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0221P)²+1.3260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.47(11)
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_number_reflns         4499
_refine_ls_number_parameters     227
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.061

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.68418(6) 0.85282(9) 0.40284(8) 0.02342(17) Uani 1 1 d . . . . .
S12 S 0.75944(6) 0.59168(10) 0.54674(9) 0.0328(2) Uani 1 1 d . . . . .
O11 O 0.6469(2) 0.9369(3) 0.3159(2) 0.0330(7) Uani 1 1 d . . . . .
O12 O 0.78811(16) 0.8405(3) 0.4090(3) 0.0304(5) Uani 1 1 d . . . . .
N11 N 0.5671(2) 1.1606(4) 0.7929(3) 0.0338(8) Uani 1 1 d . . . . .
H10 H 0.610773 1.186381 0.839256 0.051 Uiso 1 1 d R U . . .
H11 H 0.506286 1.181148 0.804176 0.051 Uiso 1 1 d R U . . .
N12 N 0.6316(2) 0.7007(3) 0.3969(3) 0.0269(6) Uani 1 1 d . . . . .
N13 N 0.6147(3) 0.4673(4) 0.4623(3) 0.0442(10) Uani 1 1 d . . . . .
C11 C 0.5939(2) 1.0886(4) 0.7038(3) 0.0221(7) Uani 1 1 d . . . . .
C12 C 0.5251(2) 1.0459(4) 0.6283(3) 0.0222(7) Uani 1 1 d . . . . .
H12 H 0.459375 1.067919 0.639469 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5523(2) 0.9729(4) 0.5389(3) 0.0221(6) Uani 1 1 d . . . . .
H13 H 0.505044 0.944280 0.489167 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6490(2) 0.9401(4) 0.5203(3) 0.0207(7) Uani 1 1 d . . . . .
C15 C 0.7166(2) 0.9803(4) 0.5952(3) 0.0247(7) Uani 1 1 d . . . . .
H15 H 0.782215 0.957007 0.584102 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6902(3) 1.0534(4) 0.6856(3) 0.0243(7) Uani 1 1 d . . . . .
H16 H 0.737691 1.079899 0.735631 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6607(3) 0.5919(4) 0.4598(3) 0.0259(7) Uani 1 1 d . . . . .
C18 C 0.6565(3) 0.3712(5) 0.5319(4) 0.0458(11) Uani 1 1 d . . . . .
H18 H 0.632056 0.276225 0.541068 0.055 Uiso 1 1 calc R U . . .
C19 C 0.7326(3) 0.4178(5) 0.5857(3) 0.0353(9) Uani 1 1 d . . . . .
H19 H 0.766620 0.363906 0.637191 0.042 Uiso 1 1 calc R U . . .
N31 N 0.4651(3) 0.3528(4) 0.3485(3) 0.0243(10) Uani 0.717(7) 1 d D . P A 1
H31 H 0.507447 0.412835 0.394614 0.037 Uiso 0.717(7) 1 calc R U P A 1
C31 C 0.3827(4) 0.3029(7) 0.4131(6) 0.0430(16) Uani 0.717(7) 1 d D . P A 1
H31A H 0.343092 0.385964 0.433009 0.064 Uiso 0.717(7) 1 calc R U P A 1
H31B H 0.406542 0.255057 0.476785 0.064 Uiso 0.717(7) 1 calc R U P A 1
H31C H 0.343997 0.234620 0.372167 0.064 Uiso 0.717(7) 1 calc R U P A 1
C32 C 0.4378(5) 0.4417(9) 0.2563(6) 0.0510(19) Uani 0.717(7) 1 d D . P A 1
H32A H 0.417371 0.539666 0.278051 0.061 Uiso 0.717(7) 1 calc R U P A 1
H32B H 0.385436 0.395702 0.215671 0.061 Uiso 0.717(7) 1 calc R U P A 1
C33 C 0.5305(6) 0.4471(14) 0.1924(6) 0.050(2) Uani 0.717(7) 1 d D . P A 1
H33A H 0.516551 0.451590 0.116002 0.060 Uiso 0.717(7) 1 calc R U P A 1
H33B H 0.569428 0.532340 0.212183 0.060 Uiso 0.717(7) 1 calc R U P A 1
C34 C 0.5819(5) 0.3098(7) 0.2197(6) 0.053(2) Uani 0.717(7) 1 d D . P A 1
H34A H 0.647197 0.331424 0.245795 0.063 Uiso 0.717(7) 1 calc R U P A 1
H34B H 0.587418 0.247442 0.156624 0.063 Uiso 0.717(7) 1 calc R U P A 1
C35 C 0.5242(6) 0.2341(6) 0.3042(6) 0.049(2) Uani 0.717(7) 1 d D . P A 1
H35A H 0.483363 0.157209 0.273781 0.059 Uiso 0.717(7) 1 calc R U P A 1
H35B H 0.566506 0.191511 0.358527 0.059 Uiso 0.717(7) 1 calc R U P A 1
N31A N 0.5012(7) 0.3717(11) 0.3015(9) 0.027(3) Uiso 0.283(7) 1 d D . P A 2
H31N H 0.551973 0.407266 0.350664 0.040 Uiso 0.283(7) 1 calc R U P A 2
C31A C 0.532(3) 0.401(4) 0.190(2) 0.112(19) Uiso 0.283(7) 1 d D . P A 2
H31D H 0.598802 0.370510 0.181093 0.167 Uiso 0.283(7) 1 calc R U P A 2
H31E H 0.526537 0.504570 0.175663 0.167 Uiso 0.283(7) 1 calc R U P A 2
H31F H 0.490904 0.347038 0.141673 0.167 Uiso 0.283(7) 1 calc R U P A 2
C32A C 0.4870(12) 0.2154(15) 0.3188(17) 0.049(5) Uiso 0.283(7) 1 d D . P A 2
H32C H 0.544349 0.171712 0.351850 0.059 Uiso 0.283(7) 1 calc R U P A 2
H32D H 0.473865 0.165327 0.251442 0.059 Uiso 0.283(7) 1 calc R U P A 2
C33A C 0.4007(9) 0.2062(15) 0.3921(13) 0.038(3) Uiso 0.283(7) 1 d D . P A 2
H33C H 0.367527 0.112197 0.385333 0.045 Uiso 0.283(7) 1 calc R U P A 2
H33D H 0.419584 0.221237 0.466462 0.045 Uiso 0.283(7) 1 calc R U P A 2
C34A C 0.3393(10) 0.3283(17) 0.3524(16) 0.049(4) Uiso 0.283(7) 1 d D . P A 2
H34C H 0.293694 0.360397 0.407291 0.059 Uiso 0.283(7) 1 calc R U P A 2
H34D H 0.302741 0.298414 0.289200 0.059 Uiso 0.283(7) 1 calc R U P A 2
C35A C 0.4096(10) 0.4475(14) 0.3256(15) 0.045(4) Uiso 0.283(7) 1 d D . P A 2
H35C H 0.387186 0.503401 0.263805 0.055 Uiso 0.283(7) 1 calc R U P A 2
H35D H 0.417722 0.514191 0.385864 0.055 Uiso 0.283(7) 1 calc R U P A 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.448(3) . ?
S11 O12 1.456(2) . ?
S11 N12 1.590(3) . ?
S11 C14 1.766(3) . ?
S12 C19 1.725(4) . ?
S12 C17 1.764(4) . ?
N11 C11 1.366(5) . ?
N11 H10 0.8800 . ?
N11 H11 0.8800 . ?
N12 C17 1.349(5) . ?
N13 C17 1.321(5) . ?
N13 C18 1.383(6) . ?
C11 C16 1.402(5) . ?
C11 C12 1.411(5) . ?
C12 C13 1.375(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.402(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(5) . ?
C15 C16 1.382(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.334(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C32 1.481(8) . ?
N31 C35 1.484(7) . ?
N31 C31 1.486(7) . ?
N31 H31 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.527(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.500(13) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.513(9) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
N31A C32A 1.477(13) . ?
N31A C35A 1.488(12) . ?
N31A C31A 1.500(14) . ?
N31A H31N 1.0000 . ?
C31A H31D 0.9800 . ?
C31A H31E 0.9800 . ?
C31A H31F 0.9800 . ?
C32A C33A 1.523(14) . ?
C32A H32C 0.9900 . ?
C32A H32D 0.9900 . ?
C33A C34A 1.505(15) . ?
C33A H33C 0.9900 . ?
C33A H33D 0.9900 . ?
C34A C35A 1.515(14) . ?
C34A H34C 0.9900 . ?
C34A H34D 0.9900 . ?
C35A H35C 0.9900 . ?
C35A H35D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 116.15(18) . . ?
O11 S11 N12 105.94(18) . . ?
O12 S11 N12 113.10(15) . . ?
O11 S11 C14 107.34(15) . . ?
O12 S11 C14 105.49(18) . . ?
N12 S11 C14 108.52(18) . . ?
C19 S12 C17 90.63(19) . . ?
C11 N11 H10 119.8 . . ?
C11 N11 H11 120.2 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 119.6(3) . . ?
C17 N13 C18 111.9(3) . . ?
N11 C11 C16 120.8(3) . . ?
N11 C11 C12 120.9(3) . . ?
C16 C11 C12 118.3(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 S11 120.8(3) . . ?
C13 C14 S11 120.5(3) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N13 C17 N12 121.3(3) . . ?
N13 C17 S12 111.3(3) . . ?
N12 C17 S12 127.3(3) . . ?
C19 C18 N13 117.0(4) . . ?
C19 C18 H18 121.5 . . ?
N13 C18 H18 121.5 . . ?
C18 C19 S12 109.2(3) . . ?
C18 C19 H19 125.4 . . ?
S12 C19 H19 125.4 . . ?
C32 N31 C35 104.8(5) . . ?
C32 N31 C31 114.2(5) . . ?
C35 N31 C31 114.1(5) . . ?
C32 N31 H31 107.8 . . ?
C35 N31 H31 107.8 . . ?
C31 N31 H31 107.8 . . ?
N31 C31 H31A 109.5 . . ?
N31 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N31 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N31 C32 C33 102.7(5) . . ?
N31 C32 H32A 111.2 . . ?
C33 C32 H32A 111.2 . . ?
N31 C32 H32B 111.2 . . ?
C33 C32 H32B 111.2 . . ?
H32A C32 H32B 109.1 . . ?
C34 C33 C32 104.7(7) . . ?
C34 C33 H33A 110.8 . . ?
C32 C33 H33A 110.8 . . ?
C34 C33 H33B 110.8 . . ?
C32 C33 H33B 110.8 . . ?
H33A C33 H33B 108.9 . . ?
C33 C34 C35 107.6(5) . . ?
C33 C34 H34A 110.2 . . ?
C35 C34 H34A 110.2 . . ?
C33 C34 H34B 110.2 . . ?
C35 C34 H34B 110.2 . . ?
H34A C34 H34B 108.5 . . ?
N31 C35 C34 102.8(5) . . ?
N31 C35 H35A 111.2 . . ?
C34 C35 H35A 111.2 . . ?
N31 C35 H35B 111.2 . . ?
C34 C35 H35B 111.2 . . ?
H35A C35 H35B 109.1 . . ?
C32A N31A C35A 108.5(9) . . ?
C32A N31A C31A 110.8(15) . . ?
C35A N31A C31A 110.7(16) . . ?
C32A N31A H31N 108.9 . . ?
C35A N31A H31N 108.9 . . ?
C31A N31A H31N 108.9 . . ?
N31A C31A H31D 109.5 . . ?
N31A C31A H31E 109.5 . . ?
H31D C31A H31E 109.5 . . ?
N31A C31A H31F 109.5 . . ?
H31D C31A H31F 109.5 . . ?
H31E C31A H31F 109.5 . . ?
N31A C32A C33A 104.6(10) . . ?
N31A C32A H32C 110.8 . . ?
C33A C32A H32C 110.8 . . ?
N31A C32A H32D 110.8 . . ?
C33A C32A H32D 110.8 . . ?
H32C C32A H32D 108.9 . . ?
C34A C33A C32A 101.7(11) . . ?
C34A C33A H33C 111.4 . . ?
C32A C33A H33C 111.4 . . ?
C34A C33A H33D 111.4 . . ?
C32A C33A H33D 111.4 . . ?
H33C C33A H33D 109.3 . . ?
C33A C34A C35A 104.8(10) . . ?
C33A C34A H34C 110.8 . . ?
C35A C34A H34C 110.8 . . ?
C33A C34A H34D 110.8 . . ?
C35A C34A H34D 110.8 . . ?
H34C C34A H34D 108.9 . . ?
N31A C35A C34A 104.9(10) . . ?
N31A C35A H35C 110.8 . . ?
C34A C35A H35C 110.8 . . ?
N31A C35A H35D 110.8 . . ?
C34A C35A H35D 110.8 . . ?
H35C C35A H35D 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 171.4(3) . . . . ?
O12 S11 N12 C17 43.0(4) . . . . ?
C14 S11 N12 C17 -73.6(3) . . . . ?
N11 C11 C12 C13 -179.7(3) . . . . ?
C16 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
C12 C13 C14 C15 1.4(5) . . . . ?
C12 C13 C14 S11 -177.4(3) . . . . ?
O11 S11 C14 C15 -124.9(3) . . . . ?
O12 S11 C14 C15 -0.4(3) . . . . ?
N12 S11 C14 C15 121.0(3) . . . . ?
O11 S11 C14 C13 53.9(3) . . . . ?
O12 S11 C14 C13 178.3(3) . . . . ?
N12 S11 C14 C13 -60.2(3) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
S11 C14 C15 C16 177.6(3) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
N11 C11 C16 C15 179.9(3) . . . . ?
C12 C11 C16 C15 0.8(5) . . . . ?
C18 N13 C17 N12 180.0(4) . . . . ?
C18 N13 C17 S12 -0.1(5) . . . . ?
S11 N12 C17 N13 175.3(3) . . . . ?
S11 N12 C17 S12 -4.6(5) . . . . ?
C19 S12 C17 N13 -0.8(3) . . . . ?
C19 S12 C17 N12 179.1(4) . . . . ?
C17 N13 C18 C19 1.3(6) . . . . ?
N13 C18 C19 S12 -1.9(6) . . . . ?
C17 S12 C19 C18 1.5(4) . . . . ?
C35 N31 C32 C33 -41.8(8) . . . . ?
C31 N31 C32 C33 -167.4(7) . . . . ?
N31 C32 C33 C34 28.1(9) . . . . ?
C32 C33 C34 C35 -4.8(9) . . . . ?
C32 N31 C35 C34 38.6(7) . . . . ?
C31 N31 C35 C34 164.2(6) . . . . ?
C33 C34 C35 N31 -20.3(9) . . . . ?
C35A N31A C32A C33A -21.2(18) . . . . ?
C31A N31A C32A C33A -143(2) . . . . ?
N31A C32A C33A C34A 36.7(18) . . . . ?
C32A C33A C34A C35A -38.6(18) . . . . ?
C32A N31A C35A C34A -2.8(19) . . . . ?
C31A N31A C35A C34A 119(2) . . . . ?
C33A C34A C35A N31A 26.2(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.88 2.19 3.004(4) 153.1 4_655 yes
N11 H11 O11 0.88 2.40 3.131(4) 140.1 2_675 yes
N11 H11 N12 0.88 2.51 3.326(4) 155.4 2_675 yes
N31^a H31^a N13 1.00 1.80 2.750(5) 158.0 . yes
N31A^b H31N^b N13 1.00 1.76 2.731(12) 164.0 . yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_68
_database_code_depnum_ccdc_archive 'CCDC 2120817'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 27n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, 1,2-ethanediamine (1:1) salt'
_chemical_name_common            'Sulfathiazole, 1,2-ethanediamine (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 S2 O2 -, C2 H9 N2 +'
_chemical_formula_sum            'C11 H17 N5 O2 S2'
_chemical_formula_weight         315.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.838(2)
_cell_length_b                   11.826(2)
_cell_length_c                   22.321(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.14(3)
_cell_angle_gamma                90
_cell_volume                     2860.9(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12059
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.381
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12059
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.564
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3207
_reflns_number_gt                2790
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  27n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.25      51     56     91.1     4.05     551.7   41.14  0.0291  0.0251
3.25 - 2.13     118    121     97.5     4.23     223.0   37.53  0.0298  0.0236
2.13 - 1.69     168    170     98.8     4.59     120.7   34.69  0.0405  0.0223
1.69 - 1.47     171    173     98.8     4.60     107.4   31.93  0.0348  0.0227
1.47 - 1.33     166    166    100.0     4.59      77.6   29.16  0.0404  0.0268
1.33 - 1.24     168    168    100.0     4.60      89.9   27.14  0.0421  0.0277
1.24 - 1.16     170    170    100.0     4.72      69.5   24.59  0.0434  0.0322
1.16 - 1.10     185    185    100.0     4.63      74.7   25.00  0.0437  0.0315
1.10 - 1.06     148    148    100.0     4.40      45.9   20.13  0.0510  0.0398
1.06 - 1.01     185    185    100.0     4.62      47.9   18.85  0.0563  0.0399
1.01 - 0.98     147    147    100.0     4.30      31.8   14.32  0.0666  0.0518
0.98 - 0.95     172    172    100.0     4.01      32.5   13.95  0.0757  0.0544
0.95 - 0.92     174    174    100.0     3.68      32.0   12.31  0.0716  0.0619
0.92 - 0.89     197    198     99.5     3.21      27.0    9.96  0.0921  0.0739
0.89 - 0.87     178    180     98.9     2.78      23.4    8.98  0.0973  0.0897
0.87 - 0.85     163    165     98.8     2.59      18.8    7.04  0.1201  0.1154
0.85 - 0.83     173    183     94.5     2.20      19.5    6.20  0.1183  0.1253
0.83 - 0.81     198    204     97.1     2.18      20.1    5.83  0.1157  0.1312
0.81 - 0.80     102    105     97.1     1.82      25.3    6.30  0.1291  0.1371
0.80 - 0.78     209    240     87.1     1.39      14.7    3.75  0.1580  0.2286
0.78 - 0.77     121    163     74.2     1.08      17.7    4.16  0.1331  0.2056
#------------------------------------------------------------------------------
0.87 - 0.77     966   1060     91.1     1.86      18.9    5.49  0.1244  0.1534
 Inf - 0.77    3364   3473     96.9     3.48      61.2   17.24  0.0462  0.0430
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
Refined as a 2-component (pseudo) merohedral twin.
Twin law: 1 0 0 / 0 1 0 / 0 0 -1
Refined BASF = 0.1039(7)
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+1.7398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3207
_refine_ls_number_parameters     211
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.062

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.47745(4) 0.78863(4) 0.63208(2) 0.01746(13) Uani 1 1 d . . . . .
S12 S 0.40734(5) 0.54230(4) 0.57988(2) 0.02365(14) Uani 1 1 d . . . . .
O11 O 0.52016(13) 0.87890(11) 0.67107(6) 0.0233(3) Uani 1 1 d . . . . .
O12 O 0.34532(12) 0.76701(11) 0.63430(6) 0.0221(3) Uani 1 1 d . . . . .
N11 N 0.60641(17) 0.91698(14) 0.38279(7) 0.0239(4) Uani 1 1 d D . . . .
H10 H 0.5517(15) 0.9604(16) 0.3646(10) 0.034(7) Uiso 1 1 d D . . . .
H11 H 0.6816(12) 0.9447(17) 0.3785(10) 0.027(6) Uiso 1 1 d D . . . .
N12 N 0.55786(15) 0.68226(13) 0.64970(7) 0.0188(3) Uani 1 1 d . . . . .
N13 N 0.61795(14) 0.49741(13) 0.62814(8) 0.0223(4) Uani 1 1 d . . . . .
C11 C 0.57381(18) 0.88945(15) 0.44105(9) 0.0189(4) Uani 1 1 d . . . . .
C12 C 0.66559(18) 0.87192(16) 0.48440(9) 0.0203(4) Uani 1 1 d . . . . .
H12 H 0.749831 0.881905 0.474003 0.024 Uiso 1 1 calc R U . . .
C13 C 0.63512(18) 0.84035(16) 0.54199(9) 0.0198(4) Uani 1 1 d . . . . .
H13 H 0.698168 0.828921 0.571003 0.024 Uiso 1 1 calc R U . . .
C14 C 0.51151(18) 0.82520(15) 0.55760(8) 0.0174(4) Uani 1 1 d . . . . .
C15 C 0.41914(18) 0.84242(15) 0.51493(8) 0.0191(4) Uani 1 1 d . . . . .
H15 H 0.334953 0.832679 0.525497 0.023 Uiso 1 1 calc R U . . .
C16 C 0.45039(18) 0.87373(15) 0.45717(9) 0.0201(4) Uani 1 1 d . . . . .
H16 H 0.387257 0.884655 0.428138 0.024 Uiso 1 1 calc R U . . .
C17 C 0.53733(17) 0.57940(16) 0.62282(8) 0.0178(4) Uani 1 1 d . . . . .
C18 C 0.57824(19) 0.40144(17) 0.59828(9) 0.0239(4) Uani 1 1 d . . . . .
H18 H 0.625127 0.333572 0.598116 0.029 Uiso 1 1 calc R U . . .
C19 C 0.46971(19) 0.40982(17) 0.56958(10) 0.0248(4) Uani 1 1 d . . . . .
H19 H 0.432557 0.351033 0.546821 0.030 Uiso 1 1 calc R U . . .
N31 N 0.77032(16) 0.45207(14) 0.74532(8) 0.0237(4) Uani 1 1 d D . . . .
H31A H 0.7434(17) 0.4485(19) 0.7077(6) 0.025(6) Uiso 1 1 d D . . . .
H31B H 0.8464(14) 0.426(2) 0.7473(10) 0.043(7) Uiso 1 1 d D . . . .
N34 N 0.77291(16) 0.19291(14) 0.75289(8) 0.0223(4) Uani 1 1 d D . . . .
H34A H 0.754(2) 0.1194(12) 0.7488(9) 0.043(7) Uiso 1 1 d D . . . .
H34B H 0.8151(17) 0.2135(16) 0.7203(6) 0.029(6) Uiso 1 1 d D . . . .
H34C H 0.8244(17) 0.1981(16) 0.7843(7) 0.026(6) Uiso 1 1 d D . . . .
C32 C 0.6911(2) 0.38311(18) 0.78366(10) 0.0270(5) Uani 1 1 d . . . . .
H32A H 0.612329 0.424056 0.789475 0.032 Uiso 1 1 calc R U . . .
H32B H 0.731148 0.376440 0.823401 0.032 Uiso 1 1 calc R U . . .
C33 C 0.66131(19) 0.26437(18) 0.76132(10) 0.0278(5) Uani 1 1 d . . . . .
H33A H 0.605835 0.227026 0.790413 0.033 Uiso 1 1 calc R U . . .
H33B H 0.616623 0.270069 0.722701 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.4524(14) . ?
S11 O12 1.4556(14) . ?
S11 N12 1.5797(16) . ?
S11 C14 1.7578(19) . ?
S12 C19 1.722(2) . ?
S12 C17 1.7576(19) . ?
N11 C11 1.387(3) . ?
N11 H10 0.883(12) . ?
N11 H11 0.883(12) . ?
N12 C17 1.374(2) . ?
N13 C17 1.310(2) . ?
N13 C18 1.384(3) . ?
C11 C16 1.398(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(3) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.342(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C32 1.462(3) . ?
N31 H31A 0.889(12) . ?
N31 H31B 0.880(12) . ?
N34 C33 1.488(3) . ?
N34 H34A 0.898(12) . ?
N34 H34B 0.894(12) . ?
N34 H34C 0.897(12) . ?
C32 C33 1.524(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 114.89(9) . . ?
O11 S11 N12 105.14(9) . . ?
O12 S11 N12 113.19(9) . . ?
O11 S11 C14 108.58(9) . . ?
O12 S11 C14 106.52(9) . . ?
N12 S11 C14 108.33(9) . . ?
C19 S12 C17 89.17(9) . . ?
C11 N11 H10 113.3(15) . . ?
C11 N11 H11 115.1(15) . . ?
H10 N11 H11 110.7(14) . . ?
C17 N12 S11 120.50(13) . . ?
C17 N13 C18 110.89(16) . . ?
N11 C11 C16 121.22(18) . . ?
N11 C11 C12 120.01(18) . . ?
C16 C11 C12 118.71(18) . . ?
C13 C12 C11 120.82(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.95(18) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.88(18) . . ?
C15 C14 S11 121.98(15) . . ?
C13 C14 S11 118.12(15) . . ?
C16 C15 C14 119.88(18) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 120.76(18) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N13 C17 N12 120.54(17) . . ?
N13 C17 S12 113.46(14) . . ?
N12 C17 S12 126.00(14) . . ?
C19 C18 N13 116.14(18) . . ?
C19 C18 H18 121.9 . . ?
N13 C18 H18 121.9 . . ?
C18 C19 S12 110.33(15) . . ?
C18 C19 H19 124.8 . . ?
S12 C19 H19 124.8 . . ?
C32 N31 H31A 109.5(15) . . ?
C32 N31 H31B 109.2(17) . . ?
H31A N31 H31B 109.7(14) . . ?
C33 N34 H34A 112.0(15) . . ?
C33 N34 H34B 111.4(14) . . ?
H34A N34 H34B 107.4(12) . . ?
C33 N34 H34C 111.5(14) . . ?
H34A N34 H34C 106.8(12) . . ?
H34B N34 H34C 107.4(12) . . ?
N31 C32 C33 116.51(18) . . ?
N31 C32 H32A 108.2 . . ?
C33 C32 H32A 108.2 . . ?
N31 C32 H32B 108.2 . . ?
C33 C32 H32B 108.2 . . ?
H32A C32 H32B 107.3 . . ?
N34 C33 C32 113.15(17) . . ?
N34 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
N34 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 177.14(15) . . . . ?
O12 S11 N12 C17 50.97(18) . . . . ?
C14 S11 N12 C17 -66.92(17) . . . . ?
N11 C11 C12 C13 -177.55(17) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C12 C13 C14 S11 -178.33(14) . . . . ?
O11 S11 C14 C15 -116.62(15) . . . . ?
O12 S11 C14 C15 7.63(17) . . . . ?
N12 S11 C14 C15 129.70(15) . . . . ?
O11 S11 C14 C13 61.46(17) . . . . ?
O12 S11 C14 C13 -174.29(14) . . . . ?
N12 S11 C14 C13 -52.22(17) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
S11 C14 C15 C16 178.48(14) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
N11 C11 C16 C15 177.74(17) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
C18 N13 C17 N12 179.28(17) . . . . ?
C18 N13 C17 S12 -0.4(2) . . . . ?
S11 N12 C17 N13 166.40(15) . . . . ?
S11 N12 C17 S12 -14.0(2) . . . . ?
C19 S12 C17 N13 -0.25(16) . . . . ?
C19 S12 C17 N12 -179.86(18) . . . . ?
C17 N13 C18 C19 1.0(3) . . . . ?
N13 C18 C19 S12 -1.2(2) . . . . ?
C17 S12 C19 C18 0.79(17) . . . . ?
N31 C32 C33 N34 60.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.883(12) 2.202(15) 3.024(2) 154.9(18) 5_676 yes
N11 H11 N13 0.883(12) 2.283(13) 3.164(2) 175.0(18) 7_666 yes
N31 H31A N13 0.889(12) 2.308(13) 3.136(3) 154.9(17) . yes
N31 H31B O11 0.880(12) 2.602(19) 3.294(2) 136.1(18) 3_545 yes
N31 H31B O11 0.880(12) 2.390(17) 3.061(2) 133.2(19) 4_646 yes
N34 H34A N31 0.898(12) 2.000(13) 2.887(2) 168.8(19) 4_646 yes
N34 H34B O12 0.894(12) 2.048(13) 2.899(2) 158.5(18) 3_545 yes
N34 H34C N12 0.897(12) 1.955(13) 2.844(2) 170.2(18) 4_646 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_65
_database_code_depnum_ccdc_archive 'CCDC 2120810'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 23n
#===============================================================================
# start Validation Reply Form
_vrf_PLAT029_65                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.915 Why?  
RESPONSE: These are the data that are available. They are essentially complete
to ca 1.00 angstrom, but the completeness tails off from there. There is no
adverse impact on the refinement.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1,1,3,3-tetramethylguanidine (1:1) salt'
_chemical_name_common            
'Sulfathiazole, 1,1,3,3-tetramethylguanidine (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 O2 S2 -, C5 H14 N3 +'
_chemical_formula_sum            'C14 H22 N6 O2 S2'
_chemical_formula_weight         370.49
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.449(2)
_cell_length_b                   13.331(3)
_cell_length_c                   13.664(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.38(3)
_cell_angle_gamma                90
_cell_volume                     1784.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15098
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.319
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15098
_diffrn_reflns_av_unetI/netI     0.1381
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.529
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measured_fraction_theta_full 0.915
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_Laue_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.906
_reflns_number_total             6430
_reflns_number_gt                4332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     0.872
_reflns_Friedel_fraction_full    0.896

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  23n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.36      51     58     87.9     5.60     138.1   47.59  0.0269  0.0182
3.36 - 2.29     123    123    100.0     7.00      59.0   44.78  0.0350  0.0192
2.29 - 1.82     168    170     98.8     7.02      37.9   36.26  0.0502  0.0227
1.82 - 1.58     169    170     99.4     7.10      28.0   28.52  0.0615  0.0275
1.58 - 1.43     173    175     98.9     6.10      18.9   22.85  0.0836  0.0391
1.43 - 1.32     177    181     97.8     5.30      17.1   19.40  0.1030  0.0459
1.32 - 1.24     176    176    100.0     4.94      18.3   17.03  0.0957  0.0502
1.24 - 1.18     163    169     96.4     4.63      16.2   16.07  0.0956  0.0557
1.18 - 1.12     195    197     99.0     4.32      13.7   13.05  0.1287  0.0687
1.12 - 1.08     150    161     93.2     3.89      14.6   12.21  0.1260  0.0718
1.08 - 1.04     177    183     96.7     3.45      10.3    8.76  0.1622  0.1001
1.04 - 1.01     156    168     92.9     3.26       8.4    7.16  0.1892  0.1280
1.01 - 0.97     224    244     91.8     3.23       8.2    6.77  0.2115  0.1374
0.97 - 0.94     175    198     88.4     3.08       6.8    5.19  0.3345  0.1756
0.94 - 0.92     133    156     85.3     2.99       5.9    4.35  0.2994  0.2138
0.92 - 0.90     144    172     83.7     2.92       5.2    3.77  0.3955  0.2565
0.90 - 0.87     225    283     79.5     2.75       5.5    3.55  0.3768  0.2664
0.87 - 0.85     172    213     80.8     2.67       5.0    2.95  0.4401  0.3243
0.85 - 0.83     176    231     76.2     2.57       4.3    2.53  0.5216  0.3930
0.83 - 0.81     196    259     75.7     2.49       4.0    2.11  0.6042  0.4717
0.81 - 0.80      86    124     69.4     2.14       4.0    1.89  0.6314  0.5047
#------------------------------------------------------------------------------
0.90 - 0.80     855   1110     77.0     2.57       4.7    2.72  0.4921  0.3639
 Inf - 0.80    3409   3811     89.5     3.97      15.9   13.13  0.0989  0.0754
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.7218P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
Flack x determined using 1482 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_number_reflns         6430
_refine_ls_number_parameters     441
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.076

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.3229(2) -0.00600(14) 0.54415(15) 0.0256(5) Uani 1 1 d . . . . .
S12 S 0.1004(2) 0.11741(16) 0.35377(16) 0.0398(6) Uani 1 1 d . . . . .
O11 O 0.3723(5) -0.0917(4) 0.6122(4) 0.0331(14) Uani 1 1 d . . . . .
O12 O 0.3254(5) -0.0157(4) 0.4390(4) 0.0315(13) Uani 1 1 d . . . . .
N11 N 0.6793(6) 0.3428(4) 0.7336(5) 0.0265(16) Uani 1 1 d . . . . .
H10 H 0.703461 0.385979 0.692508 0.040 Uiso 1 1 d R U . . .
H11 H 0.706281 0.353679 0.802888 0.040 Uiso 1 1 d R U . . .
N12 N 0.1771(6) 0.0201(4) 0.5481(4) 0.0240(15) Uani 1 1 d . . . . .
N13 N -0.0311(7) 0.1017(5) 0.4819(5) 0.0328(17) Uani 1 1 d . . . . .
C11 C 0.6005(7) 0.2600(5) 0.6907(6) 0.0219(18) Uani 1 1 d . . . . .
C12 C 0.5619(7) 0.1916(5) 0.7526(6) 0.0226(18) Uani 1 1 d . . . . .
H12 H 0.592640 0.200699 0.826133 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4793(7) 0.1110(6) 0.7080(6) 0.0236(18) Uani 1 1 d . . . . .
H13 H 0.452661 0.065807 0.751161 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4348(7) 0.0949(5) 0.6012(6) 0.0214(18) Uani 1 1 d . . . . .
C15 C 0.4770(8) 0.1603(5) 0.5399(6) 0.028(2) Uani 1 1 d . . . . .
H15 H 0.448015 0.149569 0.466680 0.034 Uiso 1 1 calc R U . . .
C16 C 0.5612(8) 0.2416(5) 0.5837(6) 0.027(2) Uani 1 1 d . . . . .
H16 H 0.591771 0.284467 0.540814 0.032 Uiso 1 1 calc R U . . .
C17 C 0.0857(8) 0.0759(5) 0.4724(6) 0.0229(19) Uani 1 1 d . . . . .
C18 C -0.1109(9) 0.1544(6) 0.3949(7) 0.041(2) Uani 1 1 d . . . . .
H18 H -0.198958 0.178177 0.389033 0.049 Uiso 1 1 calc R U . . .
C19 C -0.0602(9) 0.1706(6) 0.3200(7) 0.047(3) Uani 1 1 d . . . . .
H19 H -0.105270 0.206066 0.257115 0.056 Uiso 1 1 calc R U . . .
S21 S 0.72790(17) 0.50575(13) 0.97799(13) 0.0159(4) Uani 1 1 d . . . . .
S22 S 0.89913(19) 0.71392(14) 1.01305(15) 0.0242(5) Uani 1 1 d . . . . .
O21 O 0.6628(4) 0.4104(3) 0.9387(4) 0.0200(12) Uani 1 1 d . . . . .
O22 O 0.7719(4) 0.5147(3) 1.0914(3) 0.0208(11) Uani 1 1 d . . . . .
N21 N 0.3439(6) 0.8419(5) 0.8095(5) 0.0374(19) Uani 1 1 d . . . . .
H20 H 0.309331 0.876446 0.851191 0.056 Uiso 1 1 d R U . . .
H21 H 0.320641 0.858736 0.741721 0.056 Uiso 1 1 d R U . . .
N22 N 0.8460(5) 0.5187(4) 0.9318(4) 0.0154(13) Uani 1 1 d . . . . .
N23 N 1.0326(6) 0.6073(4) 0.9240(5) 0.0214(14) Uani 1 1 d . . . . .
C21 C 0.4314(7) 0.7637(5) 0.8485(6) 0.0207(18) Uani 1 1 d . . . . .
C22 C 0.4847(7) 0.7100(5) 0.7834(5) 0.0207(17) Uani 1 1 d . . . . .
H22 H 0.459515 0.727680 0.711779 0.025 Uiso 1 1 calc R U . . .
C23 C 0.5739(7) 0.6315(5) 0.8231(6) 0.0200(18) Uani 1 1 d . . . . .
H23 H 0.611316 0.596368 0.778852 0.024 Uiso 1 1 calc R U . . .
C24 C 0.6093(6) 0.6034(5) 0.9269(5) 0.0133(16) Uani 1 1 d . . . . .
C25 C 0.5557(6) 0.6554(5) 0.9924(6) 0.0182(17) Uani 1 1 d . . . . .
H25 H 0.580480 0.636823 1.063704 0.022 Uiso 1 1 calc R U . . .
C26 C 0.4657(7) 0.7345(5) 0.9528(6) 0.0198(18) Uani 1 1 d . . . . .
H26 H 0.427368 0.768895 0.996951 0.024 Uiso 1 1 calc R U . . .
C27 C 0.9238(7) 0.6026(5) 0.9512(5) 0.0152(16) Uani 1 1 d . . . . .
C28 C 1.0987(7) 0.6980(6) 0.9522(6) 0.0280(19) Uani 1 1 d . . . . .
H28 H 1.179536 0.712571 0.938074 0.034 Uiso 1 1 calc R U . . .
C29 C 1.0454(7) 0.7647(6) 1.0001(6) 0.0242(19) Uani 1 1 d . . . . .
H29 H 1.081537 0.829398 1.023250 0.029 Uiso 1 1 calc R U . . .
N31 N 0.1693(6) 0.4098(4) 0.4287(5) 0.0251(15) Uani 1 1 d . . . . .
N32 N 0.1712(6) 0.4453(4) 0.2641(5) 0.0231(15) Uani 1 1 d . . . . .
N33 N -0.0281(6) 0.4630(4) 0.3012(5) 0.0273(16) Uani 1 1 d . . . . .
H33A H -0.072170 0.483281 0.236887 0.041 Uiso 1 1 calc R U . . .
H33B H -0.071116 0.458543 0.346072 0.041 Uiso 1 1 calc R U . . .
C31 C 0.0997(8) 0.3656(6) 0.4940(6) 0.035(2) Uani 1 1 d . . . . .
H31A H 0.009417 0.341594 0.449814 0.053 Uiso 1 1 calc R U . . .
H31B H 0.089280 0.416346 0.542643 0.053 Uiso 1 1 calc R U . . .
H31C H 0.153527 0.309300 0.533500 0.053 Uiso 1 1 calc R U . . .
C32 C 0.3095(8) 0.4419(7) 0.4847(6) 0.043(2) Uani 1 1 d . . . . .
H32A H 0.341966 0.482677 0.438414 0.064 Uiso 1 1 calc R U . . .
H32B H 0.368134 0.382805 0.507601 0.064 Uiso 1 1 calc R U . . .
H32C H 0.312436 0.481742 0.545737 0.064 Uiso 1 1 calc R U . . .
C33 C 0.1037(8) 0.4392(5) 0.3305(6) 0.0202(17) Uani 1 1 d . . . . .
C34 C 0.1200(7) 0.5056(6) 0.1690(5) 0.0315(19) Uani 1 1 d . . . . .
H34A H 0.058458 0.557593 0.177683 0.047 Uiso 1 1 calc R U . . .
H34B H 0.070326 0.462413 0.109979 0.047 Uiso 1 1 calc R U . . .
H34C H 0.196909 0.537326 0.155595 0.047 Uiso 1 1 calc R U . . .
C35 C 0.2772(8) 0.3723(6) 0.2668(7) 0.040(2) Uani 1 1 d . . . . .
H35A H 0.285037 0.322273 0.321146 0.061 Uiso 1 1 calc R U . . .
H35B H 0.364767 0.406913 0.282116 0.061 Uiso 1 1 calc R U . . .
H35C H 0.252747 0.338796 0.198874 0.061 Uiso 1 1 calc R U . . .
N41 N 0.2499(6) 0.3998(4) 0.8385(5) 0.0220(14) Uani 1 1 d . . . . .
N42 N 0.0861(6) 0.2956(4) 0.7250(4) 0.0193(14) Uani 1 1 d . . . . .
N43 N 0.0216(6) 0.4162(4) 0.8197(4) 0.0238(15) Uani 1 1 d . . . . .
H43A H -0.063848 0.396524 0.791857 0.036 Uiso 1 1 calc R U . . .
H43B H 0.043005 0.465931 0.864930 0.036 Uiso 1 1 calc R U . . .
C41 C 0.2918(8) 0.4597(6) 0.9337(6) 0.036(2) Uani 1 1 d . . . . .
H41A H 0.232557 0.444450 0.973739 0.054 Uiso 1 1 calc R U . . .
H41B H 0.284432 0.531097 0.915525 0.054 Uiso 1 1 calc R U . . .
H41C H 0.386624 0.443772 0.975789 0.054 Uiso 1 1 calc R U . . .
C42 C 0.3387(7) 0.4072(6) 0.7763(6) 0.035(2) Uani 1 1 d . . . . .
H42A H 0.292928 0.377283 0.707454 0.052 Uiso 1 1 calc R U . . .
H42B H 0.424290 0.371393 0.811841 0.052 Uiso 1 1 calc R U . . .
H42C H 0.358506 0.477938 0.768089 0.052 Uiso 1 1 calc R U . . .
C43 C 0.1181(7) 0.3710(5) 0.7936(6) 0.0180(17) Uani 1 1 d . . . . .
C44 C -0.0568(8) 0.2752(6) 0.6622(6) 0.032(2) Uani 1 1 d . . . . .
H44A H -0.101126 0.337484 0.629389 0.048 Uiso 1 1 calc R U . . .
H44B H -0.104127 0.248521 0.707198 0.048 Uiso 1 1 calc R U . . .
H44C H -0.060801 0.225915 0.607983 0.048 Uiso 1 1 calc R U . . .
C45 C 0.1796(7) 0.2101(6) 0.7365(6) 0.0283(19) Uani 1 1 d . . . . .
H45A H 0.268038 0.225644 0.789948 0.042 Uiso 1 1 calc R U . . .
H45B H 0.192142 0.197345 0.669762 0.042 Uiso 1 1 calc R U . . .
H45C H 0.140824 0.150328 0.757386 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.450(5) . ?
S11 O12 1.451(5) . ?
S11 N12 1.582(6) . ?
S11 C14 1.775(7) . ?
S12 C19 1.730(9) . ?
S12 C17 1.769(8) . ?
N11 C11 1.380(9) . ?
N11 H10 0.9000 . ?
N11 H11 0.9001 . ?
N12 C17 1.359(9) . ?
N13 C17 1.317(9) . ?
N13 C18 1.384(10) . ?
C11 C12 1.395(10) . ?
C11 C16 1.395(10) . ?
C12 C13 1.380(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(9) . ?
C15 C16 1.393(10) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.323(11) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S21 O21 1.453(5) . ?
S21 O22 1.460(4) . ?
S21 N22 1.579(5) . ?
S21 C24 1.765(7) . ?
S22 C29 1.736(7) . ?
S22 C27 1.770(7) . ?
N21 C21 1.367(9) . ?
N21 H20 0.9001 . ?
N21 H21 0.9000 . ?
N22 C27 1.353(8) . ?
N23 C27 1.315(8) . ?
N23 C28 1.379(9) . ?
C21 C26 1.398(9) . ?
C21 C22 1.400(9) . ?
C22 C23 1.381(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.394(9) . ?
C25 C26 1.391(9) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C28 C29 1.335(10) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
N31 C33 1.336(9) . ?
N31 C31 1.458(8) . ?
N31 C32 1.460(9) . ?
N32 C33 1.330(8) . ?
N32 C34 1.462(8) . ?
N32 C35 1.466(9) . ?
N33 C33 1.332(8) . ?
N33 H33A 0.8800 . ?
N33 H33B 0.8800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
N41 C43 1.354(8) . ?
N41 C41 1.458(9) . ?
N41 C42 1.463(8) . ?
N42 C43 1.336(8) . ?
N42 C44 1.466(9) . ?
N42 C45 1.474(8) . ?
N43 C43 1.325(8) . ?
N43 H43A 0.8800 . ?
N43 H43B 0.8800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 116.1(3) . . ?
O11 S11 N12 106.5(3) . . ?
O12 S11 N12 113.7(3) . . ?
O11 S11 C14 106.4(3) . . ?
O12 S11 C14 105.4(3) . . ?
N12 S11 C14 108.3(3) . . ?
C19 S12 C17 89.3(4) . . ?
C11 N11 H10 120.1 . . ?
C11 N11 H11 119.9 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 121.6(5) . . ?
C17 N13 C18 110.4(7) . . ?
N11 C11 C12 121.3(7) . . ?
N11 C11 C16 120.0(7) . . ?
C12 C11 C16 118.6(7) . . ?
C13 C12 C11 120.6(7) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.0(7) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 118.7(7) . . ?
C15 C14 S11 120.8(6) . . ?
C13 C14 S11 120.5(6) . . ?
C14 C15 C16 121.2(7) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 119.9(7) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
N13 C17 N12 119.8(7) . . ?
N13 C17 S12 112.8(6) . . ?
N12 C17 S12 127.3(6) . . ?
C19 C18 N13 117.6(8) . . ?
C19 C18 H18 121.2 . . ?
N13 C18 H18 121.2 . . ?
C18 C19 S12 109.8(7) . . ?
C18 C19 H19 125.1 . . ?
S12 C19 H19 125.1 . . ?
O21 S21 O22 113.4(3) . . ?
O21 S21 N22 106.2(3) . . ?
O22 S21 N22 114.5(3) . . ?
O21 S21 C24 109.0(3) . . ?
O22 S21 C24 106.1(3) . . ?
N22 S21 C24 107.5(3) . . ?
C29 S22 C27 89.9(3) . . ?
C21 N21 H20 120.3 . . ?
C21 N21 H21 119.7 . . ?
H20 N21 H21 120.0 . . ?
C27 N22 S21 120.8(5) . . ?
C27 N23 C28 111.2(6) . . ?
N21 C21 C26 120.6(7) . . ?
N21 C21 C22 120.1(7) . . ?
C26 C21 C22 119.2(7) . . ?
C23 C22 C21 120.1(7) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.7(7) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 119.9(6) . . ?
C23 C24 S21 120.3(5) . . ?
C25 C24 S21 119.8(5) . . ?
C26 C25 C24 119.7(7) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 120.4(7) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
N23 C27 N22 120.2(6) . . ?
N23 C27 S22 112.2(5) . . ?
N22 C27 S22 127.5(5) . . ?
C29 C28 N23 117.9(7) . . ?
C29 C28 H28 121.1 . . ?
N23 C28 H28 121.1 . . ?
C28 C29 S22 108.8(6) . . ?
C28 C29 H29 125.6 . . ?
S22 C29 H29 125.6 . . ?
C33 N31 C31 122.9(6) . . ?
C33 N31 C32 120.7(6) . . ?
C31 N31 C32 114.9(6) . . ?
C33 N32 C34 121.5(6) . . ?
C33 N32 C35 121.2(6) . . ?
C34 N32 C35 115.2(6) . . ?
C33 N33 H33A 120.0 . . ?
C33 N33 H33B 120.0 . . ?
H33A N33 H33B 120.0 . . ?
N31 C31 H31A 109.5 . . ?
N31 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N31 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N31 C32 H32A 109.5 . . ?
N31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N32 C33 N33 121.2(7) . . ?
N32 C33 N31 119.6(7) . . ?
N33 C33 N31 119.2(7) . . ?
N32 C34 H34A 109.5 . . ?
N32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N32 C35 H35A 109.5 . . ?
N32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C43 N41 C41 120.1(6) . . ?
C43 N41 C42 120.5(6) . . ?
C41 N41 C42 115.3(6) . . ?
C43 N42 C44 120.4(6) . . ?
C43 N42 C45 120.9(6) . . ?
C44 N42 C45 114.9(6) . . ?
C43 N43 H43A 120.0 . . ?
C43 N43 H43B 120.0 . . ?
H43A N43 H43B 120.0 . . ?
N41 C41 H41A 109.5 . . ?
N41 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N41 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N41 C42 H42A 109.5 . . ?
N41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
N41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N43 C43 N42 120.2(6) . . ?
N43 C43 N41 119.9(6) . . ?
N42 C43 N41 119.8(6) . . ?
N42 C44 H44A 109.5 . . ?
N42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N42 C45 H45A 109.5 . . ?
N42 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
N42 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 -160.5(5) . . . . ?
O12 S11 N12 C17 -31.4(7) . . . . ?
C14 S11 N12 C17 85.4(6) . . . . ?
N11 C11 C12 C13 177.9(6) . . . . ?
C16 C11 C12 C13 -4.0(10) . . . . ?
C11 C12 C13 C14 1.1(10) . . . . ?
C12 C13 C14 C15 1.3(11) . . . . ?
C12 C13 C14 S11 -177.3(5) . . . . ?
O11 S11 C14 C15 139.1(6) . . . . ?
O12 S11 C14 C15 15.3(7) . . . . ?
N12 S11 C14 C15 -106.7(6) . . . . ?
O11 S11 C14 C13 -42.3(7) . . . . ?
O12 S11 C14 C13 -166.1(6) . . . . ?
N12 S11 C14 C13 71.9(6) . . . . ?
C13 C14 C15 C16 -0.8(11) . . . . ?
S11 C14 C15 C16 177.9(6) . . . . ?
C14 C15 C16 C11 -2.2(11) . . . . ?
N11 C11 C16 C15 -177.4(6) . . . . ?
C12 C11 C16 C15 4.5(10) . . . . ?
C18 N13 C17 N12 -177.5(6) . . . . ?
C18 N13 C17 S12 0.2(8) . . . . ?
S11 N12 C17 N13 -175.5(5) . . . . ?
S11 N12 C17 S12 7.1(9) . . . . ?
C19 S12 C17 N13 0.0(6) . . . . ?
C19 S12 C17 N12 177.5(7) . . . . ?
C17 N13 C18 C19 -0.4(10) . . . . ?
N13 C18 C19 S12 0.4(10) . . . . ?
C17 S12 C19 C18 -0.2(6) . . . . ?
O21 S21 N22 C27 177.8(5) . . . . ?
O22 S21 N22 C27 -56.3(6) . . . . ?
C24 S21 N22 C27 61.3(6) . . . . ?
N21 C21 C22 C23 179.6(6) . . . . ?
C26 C21 C22 C23 -2.3(10) . . . . ?
C21 C22 C23 C24 1.5(10) . . . . ?
C22 C23 C24 C25 -0.6(10) . . . . ?
C22 C23 C24 S21 -177.8(5) . . . . ?
O21 S21 C24 C23 -73.7(6) . . . . ?
O22 S21 C24 C23 163.8(5) . . . . ?
N22 S21 C24 C23 40.9(6) . . . . ?
O21 S21 C24 C25 109.2(5) . . . . ?
O22 S21 C24 C25 -13.3(6) . . . . ?
N22 S21 C24 C25 -136.2(5) . . . . ?
C23 C24 C25 C26 0.7(10) . . . . ?
S21 C24 C25 C26 177.9(5) . . . . ?
C24 C25 C26 C21 -1.6(10) . . . . ?
N21 C21 C26 C25 -179.5(6) . . . . ?
C22 C21 C26 C25 2.4(10) . . . . ?
C28 N23 C27 N22 -179.0(6) . . . . ?
C28 N23 C27 S22 0.6(7) . . . . ?
S21 N22 C27 N23 171.2(5) . . . . ?
S21 N22 C27 S22 -8.3(8) . . . . ?
C29 S22 C27 N23 -0.5(5) . . . . ?
C29 S22 C27 N22 179.0(6) . . . . ?
C27 N23 C28 C29 -0.3(10) . . . . ?
N23 C28 C29 S22 -0.1(9) . . . . ?
C27 S22 C29 C28 0.3(6) . . . . ?
C34 N32 C33 N33 19.0(10) . . . . ?
C35 N32 C33 N33 -143.9(7) . . . . ?
C34 N32 C33 N31 -160.2(7) . . . . ?
C35 N32 C33 N31 37.0(10) . . . . ?
C31 N31 C33 N32 -156.5(7) . . . . ?
C32 N31 C33 N32 38.4(10) . . . . ?
C31 N31 C33 N33 24.3(10) . . . . ?
C32 N31 C33 N33 -140.8(7) . . . . ?
C44 N42 C43 N43 12.5(10) . . . . ?
C45 N42 C43 N43 -144.4(7) . . . . ?
C44 N42 C43 N41 -169.1(6) . . . . ?
C45 N42 C43 N41 34.0(9) . . . . ?
C41 N41 C43 N43 16.5(10) . . . . ?
C42 N41 C43 N43 -139.5(7) . . . . ?
C41 N41 C43 N42 -161.9(6) . . . . ?
C42 N41 C43 N42 42.1(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O12 0.90 2.16 3.008(8) 156.9 2_656 yes
N11 H11 O21 0.90 2.19 3.005(8) 149.8 . yes
N21 H20 O22 0.90 2.28 3.121(8) 155.6 2_657 yes
N21 H21 O11 0.90 2.13 2.949(9) 151.3 1_565 yes
N33 H33A O22 0.88 2.13 2.980(7) 163.2 1_454 yes
N33 H33B N12 0.88 2.26 3.079(8) 154.8 2_556 yes
N43 H43A N11 0.88 2.62 3.493(8) 172.3 1_455 yes
N43 H43B N22 0.88 2.62 3.088(7) 114.1 1_455 yes
N43 H43B N23 0.88 2.07 2.902(8) 157.7 1_455 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_33
_database_code_depnum_ccdc_archive 'CCDC 2120807'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 6n
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_33                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The intensity diminishes rapidly as a function of resolution,
dropping below 2sigma(I) around 1.00 angstrom. Data were integrated to 0.84
angstrom resolution, but are truncated at 0.95 angstrom resolution for the
refinement.
;
_vrf_PLAT029_33                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.907 Why?  
RESPONSE: The data were collected with a point-detector instrument. The
missing data are distributed evenly through reciprocal space and there is
no adverse impact on the refinement.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, cyclohexanecarbonitrile (1:1) solvate'
_chemical_name_common            
'Sulfathiazole, cyclohexanecarbonitrile solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2 S2, C7 H11 N'
_chemical_formula_sum            'C16 H20 N4 O2 S2'
_chemical_formula_weight         364.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.112(2)
_cell_length_b                   18.994(4)
_cell_length_c                   10.590(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.37(3)
_cell_angle_gamma                90
_cell_volume                     1796.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    50
_cell_measurement_theta_min      8.20
_cell_measurement_theta_max      64.84

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.825
_shelx_estimated_absorpt_T_min   0.484
_shelx_estimated_absorpt_T_max   0.765
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'North, Phillips & Mathews, 1968'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_reflns_number            2116
_diffrn_reflns_av_unetI/netI     0.1188
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         8.199
_diffrn_reflns_theta_max         54.230
_diffrn_reflns_theta_full        54.230
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.907
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.907
_reflns_number_total             1983
_reflns_number_gt                1113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  6n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.77      43     43    100.0     1.21     583.1   31.89  0.0357  0.0198
3.77 - 2.46      99     99    100.0     1.15     229.7   24.26  0.0360  0.0307
2.46 - 1.92     144    147     98.0     1.07     133.8   19.07  0.0504  0.0423
1.92 - 1.67     146    151     96.7     1.04      73.5   13.18  0.0802  0.0635
1.67 - 1.50     144    153     94.1     1.01      61.2    9.75  0.1090  0.0865
1.50 - 1.39     145    157     92.4     0.99      43.8    7.52  0.1965  0.1372
1.39 - 1.30     141    151     93.4     0.98      34.1    5.97  0.0864  0.1778
1.30 - 1.23     159    173     91.9     0.98      31.5    5.45  0.1826  0.2033
1.23 - 1.18     115    129     89.1     0.92      31.5    5.15  0.0979  0.2150
1.18 - 1.13     161    170     94.7     1.01      27.6    4.56  0.1997  0.2412
1.13 - 1.09     134    154     87.0     0.92      18.5    3.62  0.2638  0.3339
1.09 - 1.05     146    168     86.9     0.89      17.5    3.32  0.1118  0.3655
1.05 - 1.02     138    159     86.8     0.91      11.3    2.50  0.3728  0.4881
1.02 - 0.99     149    173     86.1     0.90       8.4    1.50  0.4316  0.9598
0.99 - 0.96     160    190     84.2     0.89       6.3    1.05  0.6421  1.5440
0.96 - 0.94     118    149     79.2     0.83       5.0    0.84  0.2147  1.8753
0.94 - 0.91     192    225     85.3     0.90       5.7    0.92  0.5270  1.7558
0.91 - 0.89     156    180     86.7     0.90       4.5    0.69  0.3087  2.2469
0.89 - 0.88      78     93     83.9     0.85       3.8    0.64  0.1944  2.5327
0.88 - 0.86     211    224     94.2     0.99       4.0    0.62  0.2876  2.4342
0.86 - 0.85      71     74     95.9     1.03       3.9    0.57  0.5573  2.4603
#------------------------------------------------------------------------------
0.95 - 0.85     777    884     87.9     0.92       4.6    0.73  0.3786  2.1501
 Inf - 0.85    2850   3162     90.1     0.96      43.3    5.71  0.0621  0.1734
#================================================================================
;

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0924P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1983
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1602
_refine_ls_wR_factor_gt          0.1402
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.063

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.47858(18) 0.16340(8) 0.39130(16) 0.0534(5) Uani 1 1 d . . . . .
S12 S 0.6686(2) 0.16021(9) 0.69242(18) 0.0708(6) Uani 1 1 d . . . . .
O11 O 0.4456(5) 0.1401(2) 0.2600(4) 0.0658(13) Uani 1 1 d . . . . .
O12 O 0.5972(4) 0.2144(2) 0.4289(4) 0.0643(13) Uani 1 1 d . . . . .
N11 N -0.0813(6) 0.2660(3) 0.5300(6) 0.0736(17) Uani 1 1 d . . . . .
H10 H -0.077891 0.296128 0.596179 0.110 Uiso 1 1 d R U . . .
H11 H -0.170111 0.250318 0.486370 0.110 Uiso 1 1 d R U . . .
N12 N 0.5151(6) 0.0919(2) 0.4745(5) 0.0493(13) Uani 1 1 d . . . . .
N13 N 0.6195(5) 0.0309(3) 0.6577(5) 0.0535(13) Uani 1 1 d . . . . .
H17 H 0.588510 -0.008911 0.623794 0.080 Uiso 1 1 calc R U . . .
C11 C 0.0481(7) 0.2442(3) 0.4964(6) 0.0476(16) Uani 1 1 d . . . . .
C12 C 0.0465(7) 0.1978(3) 0.3953(6) 0.0578(18) Uani 1 1 d . . . . .
H12 H -0.045074 0.182234 0.348765 0.069 Uiso 1 1 calc R U . . .
C13 C 0.1761(7) 0.1739(3) 0.3614(5) 0.0500(16) Uani 1 1 d . . . . .
H13 H 0.171775 0.141769 0.294518 0.060 Uiso 1 1 calc R U . . .
C14 C 0.3121(7) 0.1981(3) 0.4273(6) 0.0471(15) Uani 1 1 d . . . . .
C15 C 0.3183(7) 0.2456(3) 0.5288(6) 0.0533(17) Uani 1 1 d . . . . .
H15 H 0.410087 0.261967 0.573588 0.064 Uiso 1 1 calc R U . . .
C16 C 0.1874(7) 0.2679(3) 0.5620(6) 0.0573(17) Uani 1 1 d . . . . .
H16 H 0.191793 0.299459 0.629718 0.069 Uiso 1 1 calc R U . . .
C17 C 0.5928(6) 0.0919(3) 0.5928(6) 0.0481(15) Uani 1 1 d . . . . .
C18 C 0.6996(7) 0.0363(4) 0.7816(6) 0.0642(19) Uani 1 1 d . . . . .
H18 H 0.726832 -0.002164 0.835483 0.077 Uiso 1 1 calc R U . . .
C19 C 0.7333(8) 0.1014(4) 0.8157(7) 0.073(2) Uani 1 1 d . . . . .
H19 H 0.785834 0.114575 0.896656 0.087 Uiso 1 1 calc R U . . .
N30 N 0.0826(9) 0.1004(4) 1.0314(7) 0.105(2) Uani 1 1 d . . . . .
C30 C 0.1913(13) 0.1131(5) 0.8131(12) 0.129(4) Uani 1 1 d . . . . .
H30 H 0.213530 0.162717 0.799885 0.154 Uiso 1 1 calc R U . . .
C31 C 0.0856(11) 0.0840(5) 0.6961(9) 0.113(3) Uani 1 1 d . . . . .
H31A H -0.013010 0.104204 0.691791 0.135 Uiso 1 1 calc R U . . .
H31B H 0.120499 0.097881 0.618981 0.135 Uiso 1 1 calc R U . . .
C32 C 0.0743(14) 0.0068(6) 0.6994(12) 0.162(5) Uani 1 1 d . . . . .
H32A H 0.012503 -0.005608 0.760835 0.194 Uiso 1 1 calc R U . . .
H32B H 0.022324 -0.008989 0.615293 0.194 Uiso 1 1 calc R U . . .
C33 C 0.2091(12) -0.0304(5) 0.7314(14) 0.155(5) Uani 1 1 d . . . . .
H33A H 0.257545 -0.030268 0.657640 0.186 Uiso 1 1 calc R U . . .
H33B H 0.186766 -0.079000 0.748832 0.186 Uiso 1 1 calc R U . . .
C34 C 0.3153(10) -0.0020(4) 0.8444(9) 0.103(3) Uani 1 1 d . . . . .
H34A H 0.284060 -0.017698 0.922213 0.124 Uiso 1 1 calc R U . . .
H34B H 0.413648 -0.021646 0.844949 0.124 Uiso 1 1 calc R U . . .
C35 C 0.3269(12) 0.0734(5) 0.8475(11) 0.134(4) Uani 1 1 d . . . . .
H35A H 0.375208 0.087157 0.933920 0.161 Uiso 1 1 calc R U . . .
H35B H 0.392709 0.087239 0.790183 0.161 Uiso 1 1 calc R U . . .
C36 C 0.1305(11) 0.1033(5) 0.9443(11) 0.097(3) Uani 1 1 d . . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.433(4) . ?
S11 O12 1.448(4) . ?
S11 N12 1.617(5) . ?
S11 C14 1.763(6) . ?
S12 C17 1.728(6) . ?
S12 C19 1.731(7) . ?
N11 C11 1.362(7) . ?
N11 H10 0.9000 . ?
N11 H11 0.9001 . ?
N12 C17 1.311(7) . ?
N13 C17 1.345(7) . ?
N13 C18 1.375(7) . ?
N13 H17 0.8600 . ?
C11 C12 1.384(8) . ?
C11 C16 1.396(8) . ?
C12 C13 1.377(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(8) . ?
C15 C16 1.375(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.308(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N30 C36 1.096(9) . ?
C30 C35 1.431(11) . ?
C30 C31 1.516(12) . ?
C30 C36 1.605(13) . ?
C30 H30 0.9800 . ?
C31 C32 1.469(12) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.401(12) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.484(12) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.437(10) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 118.4(3) . . ?
O11 S11 N12 104.5(3) . . ?
O12 S11 N12 110.5(3) . . ?
O11 S11 C14 107.5(3) . . ?
O12 S11 C14 108.5(3) . . ?
N12 S11 C14 106.8(2) . . ?
C17 S12 C19 90.7(3) . . ?
C11 N11 H10 119.9 . . ?
C11 N11 H11 120.1 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 122.3(4) . . ?
C17 N13 C18 115.6(6) . . ?
C17 N13 H17 122.2 . . ?
C18 N13 H17 122.2 . . ?
N11 C11 C12 121.3(6) . . ?
N11 C11 C16 121.4(6) . . ?
C12 C11 C16 117.4(6) . . ?
C13 C12 C11 122.2(6) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C14 C13 C12 119.4(6) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.2(6) . . ?
C13 C14 S11 119.5(5) . . ?
C15 C14 S11 120.1(5) . . ?
C16 C15 C14 119.3(6) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C11 121.6(6) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
N12 C17 N13 119.8(5) . . ?
N12 C17 S12 131.2(5) . . ?
N13 C17 S12 108.9(5) . . ?
C19 C18 N13 112.7(6) . . ?
C19 C18 H18 123.6 . . ?
N13 C18 H18 123.6 . . ?
C18 C19 S12 112.1(6) . . ?
C18 C19 H19 124.0 . . ?
S12 C19 H19 124.0 . . ?
C35 C30 C31 113.2(9) . . ?
C35 C30 C36 98.4(10) . . ?
C31 C30 C36 113.1(8) . . ?
C35 C30 H30 110.5 . . ?
C31 C30 H30 110.5 . . ?
C36 C30 H30 110.5 . . ?
C32 C31 C30 112.4(8) . . ?
C32 C31 H31A 109.1 . . ?
C30 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
C30 C31 H31B 109.1 . . ?
H31A C31 H31B 107.9 . . ?
C33 C32 C31 116.6(10) . . ?
C33 C32 H32A 108.1 . . ?
C31 C32 H32A 108.1 . . ?
C33 C32 H32B 108.1 . . ?
C31 C32 H32B 108.1 . . ?
H32A C32 H32B 107.3 . . ?
C32 C33 C34 114.4(8) . . ?
C32 C33 H33A 108.7 . . ?
C34 C33 H33A 108.7 . . ?
C32 C33 H33B 108.7 . . ?
C34 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
C35 C34 C33 114.5(9) . . ?
C35 C34 H34A 108.6 . . ?
C33 C34 H34A 108.6 . . ?
C35 C34 H34B 108.6 . . ?
C33 C34 H34B 108.6 . . ?
H34A C34 H34B 107.6 . . ?
C30 C35 C34 117.6(9) . . ?
C30 C35 H35A 107.9 . . ?
C34 C35 H35A 107.9 . . ?
C30 C35 H35B 107.9 . . ?
C34 C35 H35B 107.9 . . ?
H35A C35 H35B 107.2 . . ?
N30 C36 C30 175.3(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 158.8(5) . . . . ?
O12 S11 N12 C17 30.4(6) . . . . ?
C14 S11 N12 C17 -87.5(5) . . . . ?
N11 C11 C12 C13 -178.7(5) . . . . ?
C16 C11 C12 C13 1.6(9) . . . . ?
C11 C12 C13 C14 -1.8(9) . . . . ?
C12 C13 C14 C15 0.9(8) . . . . ?
C12 C13 C14 S11 175.9(4) . . . . ?
O11 S11 C14 C13 27.1(5) . . . . ?
O12 S11 C14 C13 156.3(4) . . . . ?
N12 S11 C14 C13 -84.6(5) . . . . ?
O11 S11 C14 C15 -158.0(4) . . . . ?
O12 S11 C14 C15 -28.8(5) . . . . ?
N12 S11 C14 C15 90.3(5) . . . . ?
C13 C14 C15 C16 -0.1(9) . . . . ?
S11 C14 C15 C16 -174.9(5) . . . . ?
C14 C15 C16 C11 -0.1(9) . . . . ?
N11 C11 C16 C15 179.6(6) . . . . ?
C12 C11 C16 C15 -0.7(9) . . . . ?
S11 N12 C17 N13 179.8(4) . . . . ?
S11 N12 C17 S12 2.6(8) . . . . ?
C18 N13 C17 N12 -178.9(5) . . . . ?
C18 N13 C17 S12 -1.1(6) . . . . ?
C19 S12 C17 N12 177.9(6) . . . . ?
C19 S12 C17 N13 0.5(5) . . . . ?
C17 N13 C18 C19 1.4(8) . . . . ?
N13 C18 C19 S12 -1.0(8) . . . . ?
C17 S12 C19 C18 0.3(6) . . . . ?
C35 C30 C31 C32 43.2(14) . . . . ?
C36 C30 C31 C32 -67.7(12) . . . . ?
C30 C31 C32 C33 -46.5(16) . . . . ?
C31 C32 C33 C34 46.0(17) . . . . ?
C32 C33 C34 C35 -42.3(15) . . . . ?
C31 C30 C35 C34 -42.9(15) . . . . ?
C36 C30 C35 C34 76.8(12) . . . . ?
C33 C34 C35 C30 42.1(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.90 2.09 2.989(7) 174.6 4_566 yes
N11 H11 O12 0.90 2.20 3.074(7) 165.1 1_455 yes
N13 H17 O11 0.86 2.82 3.445(6) 130.5 3_656 yes
N13 H17 N12 0.86 2.02 2.869(7) 169.5 3_656 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_69
_database_code_depnum_ccdc_archive 'CCDC 2120813'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 28n
#===============================================================================
# start Validation Reply Form
_vrf_THETM01_69                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Although the intensities are clearly strong, data are available only
to 0.99 angstrom. The structure is consequently of lower precision, but it is
clear and unambiguous (including the absolute structure and the positions of
the H atoms).
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, methylpiperazine (1:1) salt'
_chemical_name_common            'Sulfathiazole, methylpiperazine (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 O2 S2 -, C5 H13 N2 +'
_chemical_formula_sum            'C14 H21 N5 O2 S2'
_chemical_formula_weight         355.48
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.401(2)
_cell_length_b                   11.142(2)
_cell_length_c                   17.746(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1661.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6966
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      21.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.337
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6966
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.657
_diffrn_reflns_theta_max         21.030
_diffrn_reflns_theta_full        21.030
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1772
_reflns_number_gt                1597
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  28n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 4.12      16     23     69.6     5.30    1959.0   53.14  0.0654  0.0156
4.12 - 2.81      37     37    100.0    10.30    1184.8   55.85  0.0617  0.0163
2.81 - 2.23      53     53    100.0     8.38     562.3   41.51  0.0634  0.0210
2.23 - 1.96      53     53    100.0     6.96     429.0   34.67  0.0650  0.0216
1.96 - 1.76      53     53    100.0     7.09     521.3   38.29  0.0678  0.0219
1.76 - 1.62      53     53    100.0     7.00     274.6   28.33  0.1369  0.0275
1.62 - 1.52      57     57    100.0     6.18     290.4   27.42  0.1558  0.0303
1.52 - 1.44      52     52    100.0     7.00     237.4   26.25  0.0832  0.0311
1.44 - 1.37      56     56    100.0     6.29     272.9   27.69  0.0839  0.0311
1.37 - 1.32      49     50     98.0     6.30     215.5   23.81  0.0807  0.0353
1.32 - 1.26      60     60    100.0     6.37     178.3   20.46  0.0917  0.0402
1.26 - 1.22      54     54    100.0     6.33     229.4   20.18  0.0813  0.0389
1.22 - 1.18      58     58    100.0     6.43     154.9   18.19  0.1049  0.0445
1.18 - 1.15      53     53    100.0     6.08     149.5   16.91  0.1087  0.0497
1.15 - 1.12      51     52     98.1     6.33     173.2   19.47  0.1126  0.0430
1.12 - 1.10      41     41    100.0     5.54     212.1   16.45  0.1085  0.0487
1.10 - 1.07      61     61    100.0     6.10     130.6   14.53  0.1261  0.0541
1.07 - 1.05      49     50     98.0     6.24     100.8   14.07  0.1534  0.0651
1.05 - 1.03      50     53     94.3     5.25      74.5    9.28  0.1981  0.0954
1.03 - 1.01      56     56    100.0     6.07     104.3   11.84  0.1369  0.0673
1.01 - 0.99      56     56    100.0     5.61      75.1    8.77  0.1697  0.0922
#------------------------------------------------------------------------------
1.09 - 0.99     251    255     98.4     5.84      98.6   11.59  0.1487  0.0710
 Inf - 0.99    1068   1081     98.8     6.51     289.2   23.65  0.0845  0.0306
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0117P)²+0.7183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_abs_structure_details 
;
Flack x determined using 598 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_number_reflns         1772
_refine_ls_number_parameters     226
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.22099(14) 0.33310(13) 0.65422(8) 0.0297(4) Uani 1 1 d . . . . .
S12 S 0.36422(16) 0.32773(12) 0.48423(8) 0.0328(4) Uani 1 1 d . . . . .
O11 O 0.1244(4) 0.3528(3) 0.7208(2) 0.0434(11) Uani 1 1 d . . . . .
O12 O 0.2428(4) 0.2087(3) 0.6323(2) 0.0423(11) Uani 1 1 d . . . . .
N11 N 0.8598(5) 0.5493(4) 0.7063(3) 0.0321(11) Uani 1 1 d D . . . .
H10 H 0.939(5) 0.491(3) 0.714(3) 0.047(18) Uiso 1 1 d D . . . .
H11 H 0.864(6) 0.609(4) 0.743(3) 0.07(2) Uiso 1 1 d D . . . .
N12 N 0.1456(5) 0.4146(3) 0.5908(2) 0.0251(10) Uani 1 1 d . . . . .
N13 N 0.1532(5) 0.4933(4) 0.4697(2) 0.0288(11) Uani 1 1 d . . . . .
C11 C 0.7102(6) 0.4952(5) 0.6988(3) 0.0229(13) Uani 1 1 d . . . . .
C12 C 0.5727(6) 0.5544(5) 0.7205(3) 0.0277(14) Uani 1 1 d . . . . .
H12 H 0.579539 0.630716 0.744132 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4253(6) 0.5025(5) 0.7079(3) 0.0256(13) Uani 1 1 d . . . . .
H13 H 0.331551 0.543995 0.722582 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4130(5) 0.3908(4) 0.6742(3) 0.0210(13) Uani 1 1 d . . . . .
C15 C 0.5502(5) 0.3301(5) 0.6532(3) 0.0243(12) Uani 1 1 d . . . . .
H15 H 0.543134 0.253276 0.630225 0.029 Uiso 1 1 calc R U . . .
C16 C 0.6973(5) 0.3821(4) 0.6659(3) 0.0231(13) Uani 1 1 d . . . . .
H16 H 0.791155 0.340018 0.652019 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2073(5) 0.4164(4) 0.5203(3) 0.0239(13) Uani 1 1 d . . . . .
C18 C 0.2350(7) 0.4837(5) 0.4028(3) 0.0352(14) Uani 1 1 d . . . . .
H18 H 0.209589 0.532948 0.360775 0.042 Uiso 1 1 calc R U . . .
C19 C 0.3512(7) 0.4024(5) 0.3992(3) 0.0340(14) Uani 1 1 d . . . . .
H19 H 0.416725 0.387913 0.356556 0.041 Uiso 1 1 calc R U . . .
N30 N 0.8781(5) 0.5893(4) 0.5345(3) 0.0349(12) Uani 1 1 d D . . . .
H30A H 0.878(5) 0.569(4) 0.5858(17) 0.035(15) Uiso 1 1 d D . . . .
H30B H 0.977(4) 0.569(5) 0.513(2) 0.060(19) Uiso 1 1 d D . . . .
N31 N 0.7058(4) 0.6944(3) 0.4139(2) 0.0229(10) Uani 1 1 d . . . . .
C31 C 0.8338(6) 0.7593(4) 0.4504(3) 0.0278(13) Uani 1 1 d . . . . .
H31A H 0.812648 0.846628 0.447989 0.033 Uiso 1 1 calc R U . . .
H31B H 0.935466 0.743215 0.424051 0.033 Uiso 1 1 calc R U . . .
C32 C 0.8467(6) 0.7202(4) 0.5318(3) 0.0331(14) Uani 1 1 d . . . . .
H32A H 0.934385 0.764201 0.556829 0.040 Uiso 1 1 calc R U . . .
H32B H 0.746426 0.738701 0.558668 0.040 Uiso 1 1 calc R U . . .
C33 C 0.7528(7) 0.5207(5) 0.4929(3) 0.0370(15) Uani 1 1 d . . . . .
H33A H 0.779876 0.434272 0.492605 0.044 Uiso 1 1 calc R U . . .
H33B H 0.648868 0.530526 0.518539 0.044 Uiso 1 1 calc R U . . .
C34 C 0.7416(6) 0.5661(4) 0.4140(3) 0.0318(14) Uani 1 1 d . . . . .
H34A H 0.843626 0.551728 0.387531 0.038 Uiso 1 1 calc R U . . .
H34B H 0.656876 0.522115 0.386741 0.038 Uiso 1 1 calc R U . . .
C35 C 0.6822(6) 0.7381(5) 0.3372(3) 0.0373(15) Uani 1 1 d . . . . .
H35A H 0.657508 0.824065 0.338487 0.056 Uiso 1 1 calc R U . . .
H35B H 0.593733 0.694582 0.313756 0.056 Uiso 1 1 calc R U . . .
H35C H 0.779441 0.725132 0.307795 0.056 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.451(4) . ?
S11 O12 1.452(3) . ?
S11 N12 1.580(4) . ?
S11 C14 1.772(5) . ?
S12 C19 1.726(6) . ?
S12 C17 1.767(5) . ?
N11 C11 1.400(6) . ?
N11 H10 0.94(3) . ?
N11 H11 0.94(3) . ?
N12 C17 1.353(6) . ?
N13 C17 1.322(6) . ?
N13 C18 1.376(7) . ?
C11 C12 1.384(7) . ?
C11 C16 1.393(7) . ?
C12 C13 1.385(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(6) . ?
C15 C16 1.384(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.333(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N30 C32 1.483(6) . ?
N30 C33 1.495(7) . ?
N30 H30A 0.94(3) . ?
N30 H30B 0.94(3) . ?
N31 C31 1.450(6) . ?
N31 C35 1.459(6) . ?
N31 C34 1.460(6) . ?
C31 C32 1.512(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.493(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 115.7(2) . . ?
O11 S11 N12 105.6(2) . . ?
O12 S11 N12 114.2(2) . . ?
O11 S11 C14 106.9(2) . . ?
O12 S11 C14 106.6(2) . . ?
N12 S11 C14 107.4(2) . . ?
C19 S12 C17 90.0(3) . . ?
C11 N11 H10 111(3) . . ?
C11 N11 H11 114(4) . . ?
H10 N11 H11 111(2) . . ?
C17 N12 S11 120.9(3) . . ?
C17 N13 C18 111.4(4) . . ?
C12 C11 C16 118.9(5) . . ?
C12 C11 N11 121.2(4) . . ?
C16 C11 N11 119.9(5) . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.8(5) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.5(5) . . ?
C13 C14 S11 118.7(4) . . ?
C15 C14 S11 121.7(4) . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 121.1(5) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N13 C17 N12 120.4(4) . . ?
N13 C17 S12 111.8(4) . . ?
N12 C17 S12 127.8(4) . . ?
C19 C18 N13 117.3(5) . . ?
C19 C18 H18 121.3 . . ?
N13 C18 H18 121.3 . . ?
C18 C19 S12 109.4(4) . . ?
C18 C19 H19 125.3 . . ?
S12 C19 H19 125.3 . . ?
C32 N30 C33 111.2(4) . . ?
C32 N30 H30A 106(3) . . ?
C33 N30 H30A 111(3) . . ?
C32 N30 H30B 112(3) . . ?
C33 N30 H30B 107(3) . . ?
H30A N30 H30B 110(2) . . ?
C31 N31 C35 110.6(4) . . ?
C31 N31 C34 109.6(4) . . ?
C35 N31 C34 110.9(4) . . ?
N31 C31 C32 109.7(4) . . ?
N31 C31 H31A 109.7 . . ?
C32 C31 H31A 109.7 . . ?
N31 C31 H31B 109.7 . . ?
C32 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
N30 C32 C31 109.1(4) . . ?
N30 C32 H32A 109.9 . . ?
C31 C32 H32A 109.9 . . ?
N30 C32 H32B 109.9 . . ?
C31 C32 H32B 109.9 . . ?
H32A C32 H32B 108.3 . . ?
C34 C33 N30 109.5(4) . . ?
C34 C33 H33A 109.8 . . ?
N30 C33 H33A 109.8 . . ?
C34 C33 H33B 109.8 . . ?
N30 C33 H33B 109.8 . . ?
H33A C33 H33B 108.2 . . ?
N31 C34 C33 110.2(4) . . ?
N31 C34 H34A 109.6 . . ?
C33 C34 H34A 109.6 . . ?
N31 C34 H34B 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
N31 C35 H35A 109.5 . . ?
N31 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N31 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 -179.4(4) . . . . ?
O12 S11 N12 C17 -51.1(4) . . . . ?
C14 S11 N12 C17 66.8(4) . . . . ?
C16 C11 C12 C13 -1.5(8) . . . . ?
N11 C11 C12 C13 175.6(5) . . . . ?
C11 C12 C13 C14 0.6(8) . . . . ?
C12 C13 C14 C15 0.3(8) . . . . ?
C12 C13 C14 S11 -176.1(4) . . . . ?
O11 S11 C14 C13 -45.7(4) . . . . ?
O12 S11 C14 C13 -170.0(4) . . . . ?
N12 S11 C14 C13 67.3(4) . . . . ?
O11 S11 C14 C15 138.0(4) . . . . ?
O12 S11 C14 C15 13.7(5) . . . . ?
N12 S11 C14 C15 -109.0(4) . . . . ?
C13 C14 C15 C16 -0.2(7) . . . . ?
S11 C14 C15 C16 176.1(4) . . . . ?
C14 C15 C16 C11 -0.7(8) . . . . ?
C12 C11 C16 C15 1.5(8) . . . . ?
N11 C11 C16 C15 -175.6(5) . . . . ?
C18 N13 C17 N12 177.9(4) . . . . ?
C18 N13 C17 S12 -0.4(5) . . . . ?
S11 N12 C17 N13 -173.5(3) . . . . ?
S11 N12 C17 S12 4.5(6) . . . . ?
C19 S12 C17 N13 0.7(4) . . . . ?
C19 S12 C17 N12 -177.4(5) . . . . ?
C17 N13 C18 C19 -0.2(7) . . . . ?
N13 C18 C19 S12 0.7(6) . . . . ?
C17 S12 C19 C18 -0.8(4) . . . . ?
C35 N31 C31 C32 175.1(4) . . . . ?
C34 N31 C31 C32 -62.4(5) . . . . ?
C33 N30 C32 C31 -56.0(6) . . . . ?
N31 C31 C32 N30 59.3(5) . . . . ?
C32 N30 C33 C34 55.7(6) . . . . ?
C31 N31 C34 C33 62.1(5) . . . . ?
C35 N31 C34 C33 -175.5(4) . . . . ?
N30 C33 C34 N31 -57.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.94(3) 2.20(3) 3.130(6) 174(4) 1_655 yes
N11 H11 O12 0.94(3) 2.63(4) 3.478(6) 151(5) 3_656 yes
N30 H30A N11 0.94(3) 2.16(3) 3.086(6) 171(4) . yes
N30 H30B N12 0.94(3) 2.63(4) 3.136(6) 114(3) 1_655 yes
N30 H30B N13 0.94(3) 1.87(3) 2.795(6) 166(5) 1_655 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_61
_database_code_depnum_ccdc_archive 'CCDC 2120809'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 18n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 1,5-diazobicyclo[4.3.0]non-5-ene (1:1) salt'
_chemical_name_common            
'Sulfathiazole, 1,5-diazobicyclo[4.3.0]non-5-ene (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 O2 S2 -, C7 H13 N2 +'
_chemical_formula_sum            'C16 H21 N5 O2 S2'
_chemical_formula_weight         379.50
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   15.807(3)
_cell_length_b                   10.126(2)
_cell_length_c                   10.754(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1721.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11570
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      24.98

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11570
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.780
_diffrn_reflns_theta_max         24.978
_diffrn_reflns_theta_full        24.978
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2977
_reflns_number_gt                2720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.975

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  18n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.95      27     28     96.4     4.57     431.3   29.19  0.0259  0.0281
3.95 - 2.49      61     62     98.4     6.24     188.1   37.78  0.0286  0.0211
2.49 - 1.93      87     87    100.0     7.20     158.1   42.32  0.0323  0.0200
1.93 - 1.66      88     88    100.0     7.17     125.6   41.10  0.0332  0.0197
1.66 - 1.49      93     93    100.0     7.63      92.2   39.76  0.0382  0.0234
1.49 - 1.38      83     83    100.0     7.36      49.7   33.00  0.0431  0.0246
1.38 - 1.29      88     88    100.0     7.93      83.3   33.78  0.0423  0.0248
1.29 - 1.22      89     89    100.0     7.57      55.7   29.36  0.0477  0.0284
1.22 - 1.16      96     96    100.0     7.66      57.2   27.93  0.0481  0.0296
1.16 - 1.11      97     97    100.0     7.87      51.0   26.39  0.0522  0.0307
1.11 - 1.07      83     83    100.0     7.49      52.8   23.82  0.0594  0.0359
1.07 - 1.04      75     75    100.0     7.76      34.5   21.39  0.0668  0.0400
1.04 - 1.01      85     85    100.0     7.82      26.2   19.43  0.0815  0.0438
1.01 - 0.98      88     88    100.0     7.26      32.4   17.29  0.0850  0.0500
0.98 - 0.95     107    107    100.0     7.50      23.1   14.71  0.1077  0.0538
0.95 - 0.93      81     81    100.0     7.21      20.1   13.59  0.0972  0.0598
0.93 - 0.91      86     86    100.0     6.48      12.5    9.94  0.1307  0.0864
0.91 - 0.89      94     94    100.0     6.15      19.5   11.90  0.1278  0.0770
0.89 - 0.87      93     93    100.0     5.73      16.8    9.47  0.1459  0.0887
0.87 - 0.86      61     61    100.0     5.28      14.0    8.15  0.1471  0.0944
0.86 - 0.84      97    103     94.2     4.47      11.1    6.99  0.1921  0.1220
#------------------------------------------------------------------------------
0.94 - 0.84     469    475     98.7     5.73      14.9    9.53  0.1420  0.0895
 Inf - 0.84    1759   1767     99.5     6.96      60.2   23.37  0.0494  0.0313
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.2188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
Flack x determined using 1171 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.047

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.35451(5) 0.29690(8) 0.57316(8) 0.0224(2) Uani 1 1 d . . . . .
S12 S 0.54283(6) 0.03197(9) 0.46930(9) 0.0309(2) Uani 1 1 d . . . . .
O11 O 0.27605(15) 0.2268(2) 0.5474(2) 0.0276(6) Uani 1 1 d . . . . .
O12 O 0.35683(15) 0.3642(3) 0.6915(2) 0.0303(6) Uani 1 1 d . . . . .
N11 N 0.3896(2) 0.6887(3) 0.1654(3) 0.0343(8) Uani 1 1 d . . . . .
H10 H 0.441472 0.713167 0.139550 0.051 Uiso 1 1 d R U . . .
H11 H 0.343332 0.721047 0.127380 0.051 Uiso 1 1 d R U . . .
N12 N 0.43680(17) 0.2070(3) 0.5686(3) 0.0222(6) Uani 1 1 d . . . . .
N13 N 0.3960(2) 0.0891(3) 0.3804(3) 0.0283(7) Uani 1 1 d . . . . .
C11 C 0.3812(2) 0.6025(4) 0.2626(3) 0.0251(8) Uani 1 1 d . . . . .
C12 C 0.3015(2) 0.5628(4) 0.3047(3) 0.0267(8) Uani 1 1 d . . . . .
H12 H 0.252047 0.599611 0.268275 0.032 Uiso 1 1 calc R U . . .
C13 C 0.2938(2) 0.4704(3) 0.3987(3) 0.0243(8) Uani 1 1 d . . . . .
H13 H 0.239052 0.444446 0.425926 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3650(2) 0.4149(4) 0.4541(3) 0.0217(7) Uani 1 1 d . . . . .
C15 C 0.4447(2) 0.4574(4) 0.4152(3) 0.0243(8) Uani 1 1 d . . . . .
H15 H 0.493918 0.422447 0.453768 0.029 Uiso 1 1 calc R U . . .
C16 C 0.4531(2) 0.5497(4) 0.3212(3) 0.0258(8) Uani 1 1 d . . . . .
H16 H 0.507832 0.577676 0.296031 0.031 Uiso 1 1 calc R U . . .
C17 C 0.4473(2) 0.1202(3) 0.4727(3) 0.0224(7) Uani 1 1 d . . . . .
C18 C 0.4320(3) -0.0072(4) 0.3062(3) 0.0335(9) Uani 1 1 d . . . . .
H18 H 0.403180 -0.041394 0.235631 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5094(3) -0.0506(4) 0.3379(3) 0.0347(9) Uani 1 1 d . . . . .
H19 H 0.540791 -0.116242 0.294848 0.042 Uiso 1 1 calc R U . . .
N31 N 0.21687(19) 0.3086(3) 0.0852(3) 0.0284(7) Uani 1 1 d . . . . .
N32 N 0.24519(19) 0.1850(3) 0.2605(3) 0.0282(7) Uani 1 1 d . . . . .
H32 H 0.283095 0.144346 0.306594 0.042 Uiso 1 1 calc R U . . .
C31 C 0.1261(3) 0.3162(5) 0.1069(4) 0.0420(11) Uani 1 1 d . . . . .
H31A H 0.095485 0.314356 0.026527 0.050 Uiso 1 1 calc R U . . .
H31B H 0.112059 0.399946 0.149761 0.050 Uiso 1 1 calc R U . . .
C32 C 0.0994(3) 0.2006(4) 0.1858(4) 0.0401(10) Uani 1 1 d . . . . .
H32A H 0.041063 0.215712 0.216011 0.048 Uiso 1 1 calc R U . . .
H32B H 0.098856 0.119957 0.133730 0.048 Uiso 1 1 calc R U . . .
C33 C 0.1563(2) 0.1779(4) 0.2954(4) 0.0304(8) Uani 1 1 d . . . . .
H33A H 0.144328 0.245238 0.359839 0.036 Uiso 1 1 calc R U . . .
H33B H 0.144227 0.089971 0.331526 0.036 Uiso 1 1 calc R U . . .
C34 C 0.2697(2) 0.2496(4) 0.1631(3) 0.0265(8) Uani 1 1 d . . . . .
C35 C 0.3597(2) 0.2703(4) 0.1243(4) 0.0306(9) Uani 1 1 d . . . . .
H35A H 0.389874 0.185052 0.116675 0.037 Uiso 1 1 calc R U . . .
H35B H 0.390026 0.327065 0.184476 0.037 Uiso 1 1 calc R U . . .
C36 C 0.3518(3) 0.3376(6) -0.0006(4) 0.0567(15) Uani 1 1 d . . . . .
H36A H 0.367023 0.275593 -0.068227 0.068 Uiso 1 1 calc R U . . .
H36B H 0.390161 0.414777 -0.004884 0.068 Uiso 1 1 calc R U . . .
C37 C 0.2604(3) 0.3814(4) -0.0138(3) 0.0371(9) Uani 1 1 d . . . . .
H37A H 0.254950 0.477922 -0.001713 0.045 Uiso 1 1 calc R U . . .
H37B H 0.237637 0.357628 -0.096601 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.444(2) . ?
S11 O11 1.455(3) . ?
S11 N12 1.589(3) . ?
S11 C14 1.759(4) . ?
S12 C19 1.724(4) . ?
S12 C17 1.754(3) . ?
N11 C11 1.369(5) . ?
N11 H10 0.9000 . ?
N11 H11 0.9000 . ?
N12 C17 1.365(5) . ?
N13 C17 1.320(5) . ?
N13 C18 1.383(5) . ?
C11 C12 1.399(5) . ?
C11 C16 1.404(5) . ?
C12 C13 1.383(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(5) . ?
C15 C16 1.383(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.345(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C34 1.325(5) . ?
N31 C31 1.456(5) . ?
N31 C37 1.467(5) . ?
N32 C34 1.295(5) . ?
N32 C33 1.457(5) . ?
N32 H32 0.8800 . ?
C31 C32 1.507(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.499(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.496(5) . ?
C35 C36 1.511(6) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.518(6) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 114.79(15) . . ?
O12 S11 N12 106.08(16) . . ?
O11 S11 N12 114.35(15) . . ?
O12 S11 C14 108.58(17) . . ?
O11 S11 C14 105.85(15) . . ?
N12 S11 C14 106.83(15) . . ?
C19 S12 C17 90.03(19) . . ?
C11 N11 H10 120.0 . . ?
C11 N11 H11 120.0 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 119.5(2) . . ?
C17 N13 C18 110.5(3) . . ?
N11 C11 C12 121.2(3) . . ?
N11 C11 C16 120.5(3) . . ?
C12 C11 C16 118.3(3) . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 S11 120.6(3) . . ?
C15 C14 S11 120.9(3) . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N13 C17 N12 130.3(3) . . ?
N13 C17 S12 113.1(3) . . ?
N12 C17 S12 116.6(2) . . ?
C19 C18 N13 117.2(3) . . ?
C19 C18 H18 121.4 . . ?
N13 C18 H18 121.4 . . ?
C18 C19 S12 109.2(3) . . ?
C18 C19 H19 125.4 . . ?
S12 C19 H19 125.4 . . ?
C34 N31 C31 123.0(3) . . ?
C34 N31 C37 112.9(3) . . ?
C31 N31 C37 123.5(3) . . ?
C34 N32 C33 121.5(3) . . ?
C34 N32 H32 119.2 . . ?
C33 N32 H32 119.2 . . ?
N31 C31 C32 108.9(3) . . ?
N31 C31 H31A 109.9 . . ?
C32 C31 H31A 109.9 . . ?
N31 C31 H31B 109.9 . . ?
C32 C31 H31B 109.9 . . ?
H31A C31 H31B 108.3 . . ?
C33 C32 C31 113.2(4) . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C31 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
N32 C33 C32 111.6(3) . . ?
N32 C33 H33A 109.3 . . ?
C32 C33 H33A 109.3 . . ?
N32 C33 H33B 109.3 . . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?
N32 C34 N31 123.4(3) . . ?
N32 C34 C35 125.5(3) . . ?
N31 C34 C35 111.1(3) . . ?
C34 C35 C36 103.5(3) . . ?
C34 C35 H35A 111.1 . . ?
C36 C35 H35A 111.1 . . ?
C34 C35 H35B 111.1 . . ?
C36 C35 H35B 111.1 . . ?
H35A C35 H35B 109.0 . . ?
C35 C36 C37 107.0(3) . . ?
C35 C36 H36A 110.3 . . ?
C37 C36 H36A 110.3 . . ?
C35 C36 H36B 110.3 . . ?
C37 C36 H36B 110.3 . . ?
H36A C36 H36B 108.6 . . ?
N31 C37 C36 103.4(3) . . ?
N31 C37 H37A 111.1 . . ?
C36 C37 H37A 111.1 . . ?
N31 C37 H37B 111.1 . . ?
C36 C37 H37B 111.1 . . ?
H37A C37 H37B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 173.0(2) . . . . ?
O11 S11 N12 C17 45.4(3) . . . . ?
C14 S11 N12 C17 -71.4(3) . . . . ?
N11 C11 C12 C13 176.6(3) . . . . ?
C16 C11 C12 C13 -2.2(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 1.9(5) . . . . ?
C12 C13 C14 S11 -179.7(3) . . . . ?
O12 S11 C14 C13 -93.2(3) . . . . ?
O11 S11 C14 C13 30.6(3) . . . . ?
N12 S11 C14 C13 152.8(3) . . . . ?
O12 S11 C14 C15 85.2(3) . . . . ?
O11 S11 C14 C15 -151.0(3) . . . . ?
N12 S11 C14 C15 -28.8(3) . . . . ?
C13 C14 C15 C16 -1.9(5) . . . . ?
S11 C14 C15 C16 179.7(3) . . . . ?
C14 C15 C16 C11 -0.2(5) . . . . ?
N11 C11 C16 C15 -176.7(3) . . . . ?
C12 C11 C16 C15 2.2(5) . . . . ?
C18 N13 C17 N12 -178.3(3) . . . . ?
C18 N13 C17 S12 0.7(4) . . . . ?
S11 N12 C17 N13 -4.9(5) . . . . ?
S11 N12 C17 S12 176.16(18) . . . . ?
C19 S12 C17 N13 -0.7(3) . . . . ?
C19 S12 C17 N12 178.4(3) . . . . ?
C17 N13 C18 C19 -0.4(5) . . . . ?
N13 C18 C19 S12 -0.1(4) . . . . ?
C17 S12 C19 C18 0.4(3) . . . . ?
C34 N31 C31 C32 -27.1(5) . . . . ?
C37 N31 C31 C32 162.5(4) . . . . ?
N31 C31 C32 C33 46.3(5) . . . . ?
C34 N32 C33 C32 23.7(5) . . . . ?
C31 C32 C33 N32 -45.6(5) . . . . ?
C33 N32 C34 N31 -3.2(5) . . . . ?
C33 N32 C34 C35 175.6(4) . . . . ?
C31 N31 C34 N32 5.4(6) . . . . ?
C37 N31 C34 N32 176.8(3) . . . . ?
C31 N31 C34 C35 -173.6(4) . . . . ?
C37 N31 C34 C35 -2.2(4) . . . . ?
N32 C34 C35 C36 174.0(4) . . . . ?
N31 C34 C35 C36 -7.1(5) . . . . ?
C34 C35 C36 C37 13.1(5) . . . . ?
C34 N31 C37 C36 10.4(5) . . . . ?
C31 N31 C37 C36 -178.2(4) . . . . ?
C35 C36 C37 N31 -14.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 N12 0.90 2.22 3.119(4) 174.0 2_664 yes
N11 H11 O11 0.90 2.07 2.935(4) 159.8 4_554 yes
N32 H32 N13 0.88 2.03 2.879(4) 161.3 . yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_67
_database_code_depnum_ccdc_archive 'CCDC 2120811'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 26n
#===============================================================================
# start Validation Reply Form
_vrf_PLAT340_67                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01071 Ang.  
RESPONSE: This probably reflects the quality of the diffraction pattern: the
uncertainties on the metric parameters are quite large and the data are
weak at higher angle (I/sigma falling below 3.0 around 1.00 angstrom). There
is evidence of twinning: TWINROTMAT has been applied post-integration and the
structure is refined as a two-component twin. The resulting structure is of
lower precision, but it is clear and unambiguous.
;
# end Validation Reply Form
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, dimethylamine (1:1) salt'
_chemical_name_common            'Sulfathiazole, dimethylamine (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 S2 O2 -, C2 H8 N +'
_chemical_formula_sum            'C11 H16 N4 O2 S2'
_chemical_formula_weight         300.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.623(4)
_cell_length_b                   8.3200(17)
_cell_length_c                   18.157(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.64(3)
_cell_angle_gamma                90
_cell_volume                     2808.7(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12070
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      22.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.383
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15775
_diffrn_reflns_av_unetI/netI     0.1305
_diffrn_reflns_av_R_equivalents  0.1094
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.095
_diffrn_reflns_theta_max         25.080
_diffrn_reflns_theta_full        25.080
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4914
_reflns_number_gt                2735
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  26n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#--------------------------------------------------------------------------------
 Inf - 3.63      80     83     96.4     2.93     118.2   15.78  0.0237  0.0454
3.63 - 2.38     186    187     99.5     3.34      50.5   16.53  0.0316  0.0462
2.38 - 1.86     262    263     99.6     3.38      24.6   14.62  0.0507  0.0511
1.86 - 1.61     277    278     99.6     3.36      17.8   12.51  0.0621  0.0604
1.61 - 1.46     259    261     99.2     3.35      15.7    9.59  0.0695  0.0739
1.46 - 1.35     279    279    100.0     3.50      12.0    8.10  0.0851  0.0839
1.35 - 1.27     261    262     99.6     3.35      10.1    7.23  0.0996  0.1023
1.27 - 1.20     268    270     99.3     3.41      10.1    6.80  0.1083  0.1094
1.20 - 1.15     249    252     98.8     3.41       8.0    6.51  0.1198  0.1248
1.15 - 1.10     304    305     99.7     3.37       6.3    4.80  0.1517  0.1598
1.10 - 1.06     249    251     99.2     3.29       5.6    4.34  0.1779  0.1902
1.06 - 1.03     242    243     99.6     3.32       5.2    3.85  0.1999  0.2092
1.03 - 1.00     279    281     99.3     3.35       3.6    3.26  0.2587  0.2857
1.00 - 0.97     303    303    100.0     3.23       3.2    2.44  0.3032  0.3696
0.97 - 0.95     196    196    100.0     3.19       2.7    2.16  0.3444  0.4350
0.95 - 0.92     365    367     99.5     2.92       3.0    1.97  0.3504  0.4609
0.92 - 0.90     283    286     99.0     2.85       2.2    1.59  0.4115  0.6383
0.90 - 0.89     150    152     98.7     2.81       2.1    1.40  0.4231  0.7140
0.89 - 0.87     304    309     98.4     2.58       1.9    1.11  0.5621  0.8827
0.87 - 0.85     319    337     94.7     2.13       1.7    0.83  0.6179  1.1438
0.85 - 0.84     164    217     75.6     1.50       1.3    0.70  0.6210  1.5921
#--------------------------------------------------------------------------------
0.94 - 0.84    1456   1538     94.7     2.46       2.0    1.27  0.4703  0.8093
 Inf - 0.84    5279   5382     98.1     3.08      10.5    5.56  0.1026  0.1297
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+11.0760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4914
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1589
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.2265
_refine_ls_wR_factor_gt          0.1995
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.093

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.12445(9) 0.2358(2) 0.74077(11) 0.0344(5) Uani 1 1 d . . . . .
S12 S -0.03373(10) 0.3876(2) 0.67851(13) 0.0432(5) Uani 1 1 d . . . . .
O11 O 0.1842(3) 0.1274(5) 0.7584(3) 0.0413(13) Uani 1 1 d . . . . .
O12 O 0.1027(3) 0.2566(6) 0.8057(3) 0.0423(13) Uani 1 1 d . . . . .
N11 N 0.2122(3) 0.8697(7) 0.6646(4) 0.0441(16) Uani 1 1 d . . . . .
H10 H 0.199238 0.960708 0.680857 0.066 Uiso 1 1 d R U . . .
H11 H 0.237398 0.874767 0.635446 0.066 Uiso 1 1 d R U . . .
N12 N 0.0616(3) 0.1726(7) 0.6581(4) 0.0370(15) Uani 1 1 d . . . . .
N13 N -0.0594(3) 0.1772(8) 0.5657(4) 0.0440(16) Uani 1 1 d . . . . .
C11 C 0.1934(3) 0.7225(8) 0.6845(4) 0.0319(16) Uani 1 1 d . . . . .
C12 C 0.2131(3) 0.5801(8) 0.6590(4) 0.0353(18) Uani 1 1 d . . . . .
H12 H 0.240049 0.583982 0.627777 0.042 Uiso 1 1 calc R U . . .
C13 C 0.1933(4) 0.4318(9) 0.6792(4) 0.0356(18) Uani 1 1 d . . . . .
H13 H 0.208872 0.335034 0.664115 0.043 Uiso 1 1 calc R U . . .
C14 C 0.1512(4) 0.4255(8) 0.7210(4) 0.0327(17) Uani 1 1 d . . . . .
C15 C 0.1319(4) 0.5682(8) 0.7475(4) 0.0329(17) Uani 1 1 d . . . . .
H15 H 0.104167 0.564485 0.777769 0.040 Uiso 1 1 calc R U . . .
C16 C 0.1536(4) 0.7154(8) 0.7292(4) 0.0373(18) Uani 1 1 d . . . . .
H16 H 0.140879 0.811994 0.747690 0.045 Uiso 1 1 calc R U . . .
C17 C -0.0070(4) 0.2333(8) 0.6320(5) 0.0356(17) Uani 1 1 d . . . . .
C18 C -0.1231(4) 0.2601(9) 0.5486(5) 0.0419(19) Uani 1 1 d . . . . .
H18 H -0.166572 0.234823 0.502275 0.050 Uiso 1 1 calc R U . . .
C19 C -0.1201(4) 0.3758(9) 0.6001(5) 0.045(2) Uani 1 1 d . . . . .
H19 H -0.159307 0.442249 0.594945 0.054 Uiso 1 1 calc R U . . .
S21 S 0.36532(10) 0.7441(2) 0.60170(12) 0.0365(5) Uani 1 1 d . . . . .
S22 S 0.52230(11) 0.8928(3) 0.71252(14) 0.0523(6) Uani 1 1 d . . . . .
O21 O 0.3067(3) 0.6356(5) 0.5530(3) 0.0430(13) Uani 1 1 d . . . . .
O22 O 0.3788(3) 0.7630(5) 0.6855(3) 0.0415(13) Uani 1 1 d . . . . .
N21 N 0.2903(3) 1.3796(7) 0.4395(4) 0.0470(17) Uani 1 1 d . . . . .
H20 H 0.301405 1.474047 0.463073 0.071 Uiso 1 1 d R U . . .
H21 H 0.270255 1.378077 0.391183 0.071 Uiso 1 1 d R U . . .
N22 N 0.4336(3) 0.6822(7) 0.5905(4) 0.0375(15) Uani 1 1 d . . . . .
N23 N 0.5567(3) 0.6825(8) 0.6326(4) 0.0525(18) Uani 1 1 d . . . . .
C21 C 0.3045(4) 1.2316(9) 0.4783(4) 0.0339(17) Uani 1 1 d . . . . .
C22 C 0.2846(4) 1.0901(9) 0.4339(5) 0.0404(19) Uani 1 1 d . . . . .
H22 H 0.259150 1.094548 0.376080 0.049 Uiso 1 1 calc R U . . .
C23 C 0.3010(4) 0.9443(9) 0.4722(5) 0.0380(18) Uani 1 1 d . . . . .
H23 H 0.286039 0.848500 0.440866 0.046 Uiso 1 1 calc R U . . .
C24 C 0.3388(4) 0.9347(8) 0.5550(5) 0.0350(18) Uani 1 1 d . . . . .
C25 C 0.3569(4) 1.0730(9) 0.6008(5) 0.0376(18) Uani 1 1 d . . . . .
H25 H 0.381658 1.067122 0.658612 0.045 Uiso 1 1 calc R U . . .
C26 C 0.3390(4) 1.2218(8) 0.5623(5) 0.0385(18) Uani 1 1 d . . . . .
H26 H 0.350607 1.317287 0.594095 0.046 Uiso 1 1 calc R U . . .
C27 C 0.5002(4) 0.7410(9) 0.6398(4) 0.0375(18) Uani 1 1 d . . . . .
C28 C 0.6190(4) 0.7637(11) 0.6850(5) 0.057(2) Uani 1 1 d . . . . .
H28 H 0.664732 0.737148 0.687490 0.068 Uiso 1 1 calc R U . . .
C29 C 0.6117(4) 0.8793(9) 0.7311(5) 0.047(2) Uani 1 1 d . . . . .
H29 H 0.649584 0.944244 0.768428 0.056 Uiso 1 1 calc R U . . .
N30 N 0.0728(3) 0.1359(8) 0.4964(4) 0.0456(17) Uani 1 1 d . . . . .
H30A H 0.063388 0.030726 0.481951 0.068 Uiso 1 1 calc R U . . .
H30B H 0.072466 0.149014 0.545974 0.068 Uiso 1 1 calc R U . . .
C31 C 0.0164(5) 0.2361(11) 0.4359(6) 0.063(2) Uani 1 1 d . . . . .
H31A H 0.025552 0.349197 0.452192 0.094 Uiso 1 1 calc R U . . .
H31B H -0.030491 0.204270 0.432718 0.094 Uiso 1 1 calc R U . . .
H31C H 0.016450 0.221792 0.382348 0.094 Uiso 1 1 calc R U . . .
C32 C 0.1453(4) 0.1780(10) 0.5029(5) 0.049(2) Uani 1 1 d . . . . .
H32A H 0.147576 0.152317 0.451347 0.073 Uiso 1 1 calc R U . . .
H32B H 0.182068 0.116323 0.547350 0.073 Uiso 1 1 calc R U . . .
H32C H 0.154057 0.293199 0.514172 0.073 Uiso 1 1 calc R U . . .
N40 N 0.5696(4) 0.3697(9) 0.5767(4) 0.059(2) Uani 1 1 d . . . . .
H40A H 0.561970 0.475046 0.583886 0.089 Uiso 1 1 calc R U . . .
H40B H 0.571109 0.358603 0.527606 0.089 Uiso 1 1 calc R U . . .
C41 C 0.6411(4) 0.3107(11) 0.6469(5) 0.057(2) Uani 1 1 d . . . . .
H41A H 0.645599 0.194283 0.642191 0.085 Uiso 1 1 calc R U . . .
H41B H 0.641102 0.335577 0.699608 0.085 Uiso 1 1 calc R U . . .
H41C H 0.681705 0.364943 0.643021 0.085 Uiso 1 1 calc R U . . .
C42 C 0.5140(6) 0.2728(13) 0.5796(6) 0.084(3) Uani 1 1 d . . . . .
H42A H 0.513235 0.285492 0.632869 0.126 Uiso 1 1 calc R U . . .
H42B H 0.522880 0.159839 0.571612 0.126 Uiso 1 1 calc R U . . .
H42C H 0.467589 0.306185 0.536314 0.126 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.442(5) . ?
S11 O11 1.448(5) . ?
S11 N12 1.589(6) . ?
S11 C14 1.759(7) . ?
S12 C19 1.736(8) . ?
S12 C17 1.752(7) . ?
N11 C11 1.379(8) . ?
N11 H10 0.8949 . ?
N11 H11 0.8884 . ?
N12 C17 1.378(9) . ?
N13 C17 1.308(9) . ?
N13 C18 1.395(9) . ?
C11 C16 1.384(9) . ?
C11 C12 1.396(9) . ?
C12 C13 1.398(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(9) . ?
C15 C16 1.392(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.325(10) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S21 O22 1.433(5) . ?
S21 O21 1.460(5) . ?
S21 N22 1.593(6) . ?
S21 C24 1.770(7) . ?
S22 C29 1.729(8) . ?
S22 C27 1.740(8) . ?
N21 C21 1.386(9) . ?
N21 H20 0.8766 . ?
N21 H21 0.7909 . ?
N22 C27 1.365(9) . ?
N23 C27 1.320(9) . ?
N23 C28 1.398(10) . ?
C21 C26 1.378(10) . ?
C21 C22 1.385(10) . ?
C22 C23 1.367(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.364(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(10) . ?
C25 C26 1.390(10) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C28 C29 1.326(11) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
N30 C31 1.465(10) . ?
N30 C32 1.491(9) . ?
N30 H30A 0.9100 . ?
N30 H30B 0.9100 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
N40 C42 1.421(11) . ?
N40 C41 1.553(10) . ?
N40 H40A 0.9100 . ?
N40 H40B 0.9100 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 115.5(3) . . ?
O12 S11 N12 113.3(3) . . ?
O11 S11 N12 105.7(3) . . ?
O12 S11 C14 107.2(3) . . ?
O11 S11 C14 107.0(3) . . ?
N12 S11 C14 107.7(3) . . ?
C19 S12 C17 89.4(4) . . ?
C11 N11 H10 120.4 . . ?
C11 N11 H11 120.1 . . ?
H10 N11 H11 119.5 . . ?
C17 N12 S11 120.0(5) . . ?
C17 N13 C18 110.6(6) . . ?
N11 C11 C16 119.9(6) . . ?
N11 C11 C12 120.7(6) . . ?
C16 C11 C12 119.4(6) . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.2(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.8(6) . . ?
C13 C14 S11 118.3(5) . . ?
C15 C14 S11 121.9(5) . . ?
C16 C15 C14 119.7(6) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C11 C16 C15 120.7(6) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N13 C17 N12 120.2(6) . . ?
N13 C17 S12 113.4(5) . . ?
N12 C17 S12 126.4(6) . . ?
C19 C18 N13 116.8(7) . . ?
C19 C18 H18 121.6 . . ?
N13 C18 H18 121.6 . . ?
C18 C19 S12 109.8(6) . . ?
C18 C19 H19 125.1 . . ?
S12 C19 H19 125.1 . . ?
O22 S21 O21 116.1(3) . . ?
O22 S21 N22 113.3(3) . . ?
O21 S21 N22 105.6(3) . . ?
O22 S21 C24 106.7(3) . . ?
O21 S21 C24 105.1(3) . . ?
N22 S21 C24 109.6(3) . . ?
C29 S22 C27 90.4(4) . . ?
C21 N21 H20 126.4 . . ?
C21 N21 H21 116.3 . . ?
H20 N21 H21 117.2 . . ?
C27 N22 S21 119.7(5) . . ?
C27 N23 C28 110.2(7) . . ?
C26 C21 C22 118.4(7) . . ?
C26 C21 N21 120.7(7) . . ?
C22 C21 N21 121.0(7) . . ?
C23 C22 C21 120.8(7) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.7(7) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.6(7) . . ?
C23 C24 S21 119.4(6) . . ?
C25 C24 S21 121.0(6) . . ?
C24 C25 C26 119.9(7) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 120.4(7) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
N23 C27 N22 118.9(7) . . ?
N23 C27 S22 113.0(6) . . ?
N22 C27 S22 128.0(5) . . ?
C29 C28 N23 117.3(7) . . ?
C29 C28 H28 121.4 . . ?
N23 C28 H28 121.4 . . ?
C28 C29 S22 109.1(6) . . ?
C28 C29 H29 125.5 . . ?
S22 C29 H29 125.5 . . ?
C31 N30 C32 111.7(6) . . ?
C31 N30 H30A 109.3 . . ?
C32 N30 H30A 109.3 . . ?
C31 N30 H30B 109.3 . . ?
C32 N30 H30B 109.3 . . ?
H30A N30 H30B 107.9 . . ?
N30 C31 H31A 109.5 . . ?
N30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N30 C32 H32A 109.5 . . ?
N30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C42 N40 C41 106.6(8) . . ?
C42 N40 H40A 110.4 . . ?
C41 N40 H40A 110.4 . . ?
C42 N40 H40B 110.4 . . ?
C41 N40 H40B 110.4 . . ?
H40A N40 H40B 108.6 . . ?
N40 C41 H41A 109.5 . . ?
N40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N40 C42 H42A 109.5 . . ?
N40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
N40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 41.4(6) . . . . ?
O11 S11 N12 C17 168.8(5) . . . . ?
C14 S11 N12 C17 -77.0(6) . . . . ?
N11 C11 C12 C13 -179.6(7) . . . . ?
C16 C11 C12 C13 -0.6(10) . . . . ?
C11 C12 C13 C14 3.2(11) . . . . ?
C12 C13 C14 C15 -3.9(11) . . . . ?
C12 C13 C14 S11 177.2(5) . . . . ?
O12 S11 C14 C13 161.5(6) . . . . ?
O11 S11 C14 C13 37.1(7) . . . . ?
N12 S11 C14 C13 -76.2(6) . . . . ?
O12 S11 C14 C15 -17.4(7) . . . . ?
O11 S11 C14 C15 -141.8(6) . . . . ?
N12 S11 C14 C15 104.9(6) . . . . ?
C13 C14 C15 C16 2.0(11) . . . . ?
S11 C14 C15 C16 -179.1(6) . . . . ?
N11 C11 C16 C15 177.7(7) . . . . ?
C12 C11 C16 C15 -1.3(11) . . . . ?
C14 C15 C16 C11 0.6(11) . . . . ?
C18 N13 C17 N12 -177.3(6) . . . . ?
C18 N13 C17 S12 1.6(8) . . . . ?
S11 N12 C17 N13 -177.4(5) . . . . ?
S11 N12 C17 S12 3.8(9) . . . . ?
C19 S12 C17 N13 -1.9(6) . . . . ?
C19 S12 C17 N12 176.9(7) . . . . ?
C17 N13 C18 C19 -0.3(10) . . . . ?
N13 C18 C19 S12 -1.2(9) . . . . ?
C17 S12 C19 C18 1.7(6) . . . . ?
O22 S21 N22 C27 -40.3(6) . . . . ?
O21 S21 N22 C27 -168.5(5) . . . . ?
C24 S21 N22 C27 78.8(6) . . . . ?
C26 C21 C22 C23 -2.4(10) . . . . ?
N21 C21 C22 C23 177.6(6) . . . . ?
C21 C22 C23 C24 -1.3(11) . . . . ?
C22 C23 C24 C25 3.7(10) . . . . ?
C22 C23 C24 S21 -175.0(5) . . . . ?
O22 S21 C24 C23 -159.1(5) . . . . ?
O21 S21 C24 C23 -35.2(6) . . . . ?
N22 S21 C24 C23 77.9(6) . . . . ?
O22 S21 C24 C25 22.3(6) . . . . ?
O21 S21 C24 C25 146.2(6) . . . . ?
N22 S21 C24 C25 -100.7(6) . . . . ?
C23 C24 C25 C26 -2.3(10) . . . . ?
S21 C24 C25 C26 176.3(5) . . . . ?
C22 C21 C26 C25 3.7(10) . . . . ?
N21 C21 C26 C25 -176.2(6) . . . . ?
C24 C25 C26 C21 -1.5(10) . . . . ?
C28 N23 C27 N22 177.0(7) . . . . ?
C28 N23 C27 S22 -1.5(8) . . . . ?
S21 N22 C27 N23 176.6(5) . . . . ?
S21 N22 C27 S22 -5.2(9) . . . . ?
C29 S22 C27 N23 1.8(6) . . . . ?
C29 S22 C27 N22 -176.5(7) . . . . ?
C27 N23 C28 C29 0.3(11) . . . . ?
N23 C28 C29 S22 1.1(10) . . . . ?
C27 S22 C29 C28 -1.6(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.89 2.09 2.947(7) 159.3 1_565 yes
N21 H20 O21 0.88 2.08 2.881(8) 151.2 1_565 yes
N21 H21 O11 0.79 2.29 3.061(8) 163.8 4_575 yes
N30 H30A N13 0.91 1.92 2.804(9) 163.4 3_556 yes
N30 H30B N12 0.91 2.15 3.059(8) 174.7 . yes
N40 H40A N23 0.91 1.96 2.848(9) 163.4 . yes
N40 H40B N22 0.91 2.13 3.039(9) 174.7 3_666 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_64
_database_code_depnum_ccdc_archive 'CCDC 2120812'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 22n
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
'Sulfathiazole, 2-methyl-2-imadazoline (1:1) salt'
_chemical_name_common            
'Sulfathiazole, 2-methyl-2-imadazoline (1:1) salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N3 O2 S2 -, C4 H9 N2 +'
_chemical_formula_sum            'C13 H17 N5 O2 S2'
_chemical_formula_weight         339.43
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   17.562(4)
_cell_length_b                   42.720(9)
_cell_length_c                   8.291(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6220(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13502
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      29.74

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             2848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.357
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13502
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -57
_diffrn_reflns_limit_k_max       55
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.615
_diffrn_reflns_theta_max         29.739
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.756
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             3364
_reflns_number_gt                2900
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.673
_reflns_Friedel_fraction_full    0.886

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  22n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.29      31     37     83.8     8.05     316.3   66.55  0.0279  0.0145
3.29 - 2.14      72     76     94.7     9.78     113.1   62.64  0.0281  0.0140
2.14 - 1.68     100    106     94.3     8.95      77.2   50.88  0.0347  0.0176
1.68 - 1.46     101    106     95.3     8.98      54.1   44.09  0.0407  0.0203
1.46 - 1.32     102    109     93.6     8.24      42.2   33.71  0.0444  0.0251
1.32 - 1.21     105    112     93.8     7.86      44.7   33.03  0.0472  0.0288
1.21 - 1.14     106    110     96.4     8.01      38.1   29.78  0.0534  0.0291
1.14 - 1.08      97     99     98.0     7.42      30.8   25.29  0.0619  0.0392
1.08 - 1.03     108    109     99.1     8.10      27.2   24.45  0.0668  0.0377
1.03 - 0.99     110    110    100.0     7.57      20.3   19.69  0.0806  0.0442
0.99 - 0.96      90     91     98.9     8.15      17.7   18.95  0.0922  0.0451
0.96 - 0.93      99     99    100.0     8.40      13.6   14.95  0.1131  0.0557
0.93 - 0.90     113    114     99.1     7.32      15.4   15.09  0.1075  0.0545
0.90 - 0.88      82     82    100.0     6.61       9.5   11.44  0.1458  0.0824
0.88 - 0.85     150    150    100.0     6.23      10.2   10.16  0.1526  0.0885
0.85 - 0.83      98     98    100.0     5.66       9.9    8.67  0.2127  0.1026
0.83 - 0.81     101    116     87.1     3.61       8.8    6.49  0.2093  0.1455
0.81 - 0.79     121    142     85.2     2.76       7.8    5.56  0.2492  0.1843
0.79 - 0.78      49     69     71.0     2.03       7.5    5.04  0.2029  0.2036
0.78 - 0.76      91    143     63.6     1.28       5.4    2.94  0.2949  0.3316
0.76 - 0.72     107    397     27.0     0.34       5.7    2.47  0.2055  0.3672
#------------------------------------------------------------------------------
0.82 - 0.72     419    810     51.7     1.30       6.8    4.23  0.2361  0.2468
 Inf - 0.72    2033   2475     82.1     5.56      31.3   21.52  0.0521  0.0392
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1099 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_number_reflns         3364
_refine_ls_number_parameters     217
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.070

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.23375(4) 0.43156(2) 0.32532(8) 0.02148(19) Uani 1 1 d . . . . .
S12 S 0.28568(4) 0.49822(2) 0.46914(10) 0.0235(2) Uani 1 1 d . . . . .
O11 O 0.22027(11) 0.40463(6) 0.2217(3) 0.0271(5) Uani 1 1 d . . . . .
O12 O 0.16752(12) 0.45100(6) 0.3566(3) 0.0277(6) Uani 1 1 d . . . . .
N11 N 0.31977(16) 0.37660(7) 0.9606(3) 0.0266(6) Uani 1 1 d D . . . .
H10 H 0.3102(19) 0.3879(9) 1.044(4) 0.046(12) Uiso 1 1 d D . . . .
H11 H 0.3646(15) 0.3684(9) 0.968(4) 0.044(12) Uiso 1 1 d D . . . .
N12 N 0.30316(14) 0.44925(7) 0.2474(3) 0.0240(6) Uani 1 1 d . . . . .
N13 N 0.39325(13) 0.48919(7) 0.2621(3) 0.0231(6) Uani 1 1 d . . . . .
C11 C 0.30396(17) 0.39087(8) 0.8128(4) 0.0209(6) Uani 1 1 d . . . . .
C12 C 0.33633(18) 0.37987(8) 0.6700(4) 0.0229(7) Uani 1 1 d . . . . .
H12 H 0.372651 0.363403 0.674065 0.027 Uiso 1 1 calc R U . . .
C13 C 0.31629(17) 0.39259(8) 0.5227(4) 0.0220(7) Uani 1 1 d . . . . .
H13 H 0.339414 0.385033 0.426757 0.026 Uiso 1 1 calc R U . . .
C14 C 0.26215(16) 0.41653(8) 0.5144(4) 0.0206(7) Uani 1 1 d . . . . .
C15 C 0.23119(16) 0.42828(8) 0.6572(4) 0.0201(7) Uani 1 1 d . . . . .
H15 H 0.195288 0.444892 0.653288 0.024 Uiso 1 1 calc R U . . .
C16 C 0.25258(16) 0.41581(8) 0.8044(4) 0.0220(7) Uani 1 1 d . . . . .
H16 H 0.232096 0.424308 0.900984 0.026 Uiso 1 1 calc R U . . .
C17 C 0.32875(16) 0.47650(8) 0.3131(4) 0.0207(6) Uani 1 1 d . . . . .
C18 C 0.41020(17) 0.51593(8) 0.3488(4) 0.0238(7) Uani 1 1 d . . . . .
H18 H 0.454584 0.527933 0.327187 0.029 Uiso 1 1 calc R U . . .
C19 C 0.36084(17) 0.52413(8) 0.4652(4) 0.0237(7) Uani 1 1 d . . . . .
H19 H 0.366535 0.541608 0.535027 0.028 Uiso 1 1 calc R U . . .
N31 N 0.47676(15) 0.43228(8) 0.7819(3) 0.0275(7) Uani 1 1 d D . . . .
H31 H 0.5015(17) 0.4158(7) 0.755(4) 0.023(9) Uiso 1 1 d D . . . .
N32 N 0.43519(15) 0.46714(7) 0.9521(3) 0.0252(6) Uani 1 1 d D . . . .
H32 H 0.425(2) 0.4749(11) 1.047(4) 0.058(14) Uiso 1 1 d D . . . .
C31 C 0.5029(2) 0.42215(9) 1.0700(5) 0.0363(9) Uani 1 1 d . . . . .
H31A H 0.475255 0.427318 1.169201 0.054 Uiso 1 1 calc R U . . .
H31B H 0.556996 0.427102 1.083899 0.054 Uiso 1 1 calc R U . . .
H31C H 0.497156 0.399781 1.046836 0.054 Uiso 1 1 calc R U . . .
C32 C 0.47151(17) 0.44073(8) 0.9338(4) 0.0233(7) Uani 1 1 d . . . . .
C33 C 0.4434(2) 0.45606(9) 0.6759(4) 0.0286(8) Uani 1 1 d . . . . .
H33A H 0.404779 0.446828 0.603098 0.034 Uiso 1 1 calc R U . . .
H33B H 0.482953 0.466642 0.610673 0.034 Uiso 1 1 calc R U . . .
C34 C 0.40677(18) 0.47872(9) 0.7974(4) 0.0274(7) Uani 1 1 d . . . . .
H34A H 0.423349 0.500544 0.777809 0.033 Uiso 1 1 calc R U . . .
H34B H 0.350504 0.477704 0.792433 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O12 1.452(2) . ?
S11 O11 1.455(2) . ?
S11 N12 1.573(3) . ?
S11 C14 1.766(3) . ?
S12 C19 1.723(3) . ?
S12 C17 1.762(3) . ?
N11 C11 1.397(4) . ?
N11 H10 0.86(2) . ?
N11 H11 0.86(2) . ?
N12 C17 1.362(4) . ?
N13 C17 1.325(4) . ?
N13 C18 1.383(4) . ?
C11 C12 1.395(4) . ?
C11 C16 1.398(4) . ?
C12 C13 1.382(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.398(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(4) . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.344(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N31 C32 1.313(5) . ?
N31 C33 1.465(5) . ?
N31 H31 0.85(2) . ?
N32 C32 1.305(4) . ?
N32 C34 1.462(4) . ?
N32 H32 0.87(2) . ?
C31 C32 1.487(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C33 C34 1.538(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S11 O11 115.29(14) . . ?
O12 S11 N12 114.77(15) . . ?
O11 S11 N12 105.27(14) . . ?
O12 S11 C14 106.01(14) . . ?
O11 S11 C14 106.41(15) . . ?
N12 S11 C14 108.69(15) . . ?
C19 S12 C17 89.75(15) . . ?
C11 N11 H10 115(3) . . ?
C11 N11 H11 115(3) . . ?
H10 N11 H11 110(2) . . ?
C17 N12 S11 120.1(2) . . ?
C17 N13 C18 110.8(3) . . ?
C12 C11 N11 121.1(3) . . ?
C12 C11 C16 118.5(3) . . ?
N11 C11 C16 120.3(3) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 S11 120.8(2) . . ?
C13 C14 S11 120.1(2) . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N13 C17 N12 120.3(3) . . ?
N13 C17 S12 112.7(2) . . ?
N12 C17 S12 127.0(2) . . ?
C19 C18 N13 116.7(3) . . ?
C19 C18 H18 121.6 . . ?
N13 C18 H18 121.6 . . ?
C18 C19 S12 109.9(3) . . ?
C18 C19 H19 125.0 . . ?
S12 C19 H19 125.0 . . ?
C32 N31 C33 110.9(3) . . ?
C32 N31 H31 121(3) . . ?
C33 N31 H31 128(3) . . ?
C32 N32 C34 110.9(3) . . ?
C32 N32 H32 122(3) . . ?
C34 N32 H32 126(3) . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N32 C32 N31 112.6(3) . . ?
N32 C32 C31 123.7(3) . . ?
N31 C32 C31 123.8(3) . . ?
N31 C33 C34 102.2(3) . . ?
N31 C33 H33A 111.3 . . ?
C34 C33 H33A 111.3 . . ?
N31 C33 H33B 111.3 . . ?
C34 C33 H33B 111.3 . . ?
H33A C33 H33B 109.2 . . ?
N32 C34 C33 102.6(3) . . ?
N32 C34 H34A 111.2 . . ?
C33 C34 H34A 111.2 . . ?
N32 C34 H34B 111.2 . . ?
C33 C34 H34B 111.2 . . ?
H34A C34 H34B 109.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 S11 N12 C17 49.9(3) . . . . ?
O11 S11 N12 C17 177.7(2) . . . . ?
C14 S11 N12 C17 -68.6(3) . . . . ?
N11 C11 C12 C13 175.3(3) . . . . ?
C16 C11 C12 C13 -2.1(5) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C15 2.7(5) . . . . ?
C12 C13 C14 S11 -177.3(3) . . . . ?
O12 S11 C14 C15 -11.2(3) . . . . ?
O11 S11 C14 C15 -134.4(3) . . . . ?
N12 S11 C14 C15 112.7(3) . . . . ?
O12 S11 C14 C13 168.8(3) . . . . ?
O11 S11 C14 C13 45.6(3) . . . . ?
N12 S11 C14 C13 -67.3(3) . . . . ?
C13 C14 C15 C16 -1.5(5) . . . . ?
S11 C14 C15 C16 178.5(2) . . . . ?
C14 C15 C16 C11 -1.5(5) . . . . ?
C12 C11 C16 C15 3.3(5) . . . . ?
N11 C11 C16 C15 -174.1(3) . . . . ?
C18 N13 C17 N12 -177.6(3) . . . . ?
C18 N13 C17 S12 1.4(3) . . . . ?
S11 N12 C17 N13 170.7(2) . . . . ?
S11 N12 C17 S12 -8.2(4) . . . . ?
C19 S12 C17 N13 -2.0(3) . . . . ?
C19 S12 C17 N12 176.9(3) . . . . ?
C17 N13 C18 C19 0.2(4) . . . . ?
N13 C18 C19 S12 -1.7(4) . . . . ?
C17 S12 C19 C18 2.0(2) . . . . ?
C34 N32 C32 N31 3.4(4) . . . . ?
C34 N32 C32 C31 -176.1(3) . . . . ?
C33 N31 C32 N32 3.0(4) . . . . ?
C33 N31 C32 C31 -177.5(3) . . . . ?
C32 N31 C33 C34 -7.5(4) . . . . ?
C32 N32 C34 C33 -7.8(4) . . . . ?
N31 C33 C34 N32 8.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 O11 0.86(2) 2.27(3) 3.029(4) 146(3) 1_556 yes
N11 H11 O11 0.86(2) 2.10(2) 2.962(4) 175(3) 7 yes
N31 H31 N11 0.85(2) 2.20(2) 3.057(4) 174(4) 7_554 yes
N32 H32 N13 0.87(2) 1.96(3) 2.835(4) 174(4) 1_556 yes

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_89
_database_code_depnum_ccdc_archive 'CCDC 2120815'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
# working code: 16n
#-------------------------------------------------------------------------------
# NOTE: space group effectively P21/c, but sparteine molecule breaks symmetry
#===============================================================================
_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        'Sulfathiazole, (-)-sparteine (2:1) mixed salt'
_chemical_name_common            'Sulfathiazole, (-)-sparteine (2:1) mixed salt'
_chemical_melting_point          ?
_chemical_formula_moiety         
'C9 H9 N3 O2 S2, C9 H8 N3 O2 S2 -, C15 H27 N2 +'
_chemical_formula_sum            'C33 H44 N8 O4 S4'
_chemical_formula_weight         745.00
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   16.676(3)
_cell_length_b                   11.771(2)
_cell_length_c                   19.062(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.71(3)
_cell_angle_gamma                90
_cell_volume                     3476.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    27570
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.325
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR591 rotating anode'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27570
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.644
_diffrn_reflns_theta_max         25.043
_diffrn_reflns_theta_full        25.043
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             11517
_reflns_number_gt                9803
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_max     0.874
_reflns_Friedel_fraction_full    0.874

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  16n.hkl
#================================================================================
 Resolution  #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#================================================================================
 Inf - 3.58      99    102     97.1     3.80     371.3   37.30  0.0227  0.0262
3.58 - 2.34     224    224    100.0     4.51     173.5   39.01  0.0237  0.0214
2.34 - 1.84     330    330    100.0     4.66     114.8   38.58  0.0256  0.0218
1.84 - 1.60     329    329    100.0     4.69      74.3   33.94  0.0328  0.0246
1.60 - 1.45     320    320    100.0     4.72      56.3   30.28  0.0374  0.0266
1.45 - 1.34     345    345    100.0     4.70      56.0   27.92  0.0379  0.0292
1.34 - 1.26     324    324    100.0     4.69      47.0   25.18  0.0443  0.0312
1.26 - 1.20     298    298    100.0     4.74      43.3   24.59  0.0509  0.0347
1.20 - 1.15     313    313    100.0     4.66      47.3   23.02  0.0475  0.0355
1.15 - 1.10     358    358    100.0     4.63      35.6   19.34  0.0585  0.0420
1.10 - 1.06     313    313    100.0     4.73      32.0   18.26  0.0619  0.0431
1.06 - 1.03     300    300    100.0     4.59      23.3   15.39  0.0754  0.0520
1.03 - 1.00     322    322    100.0     4.64      20.6   14.06  0.0840  0.0570
1.00 - 0.97     360    360    100.0     4.58      15.2   11.17  0.1166  0.0723
0.97 - 0.95     284    284    100.0     4.27      15.5   11.08  0.1143  0.0752
0.95 - 0.92     447    447    100.0     4.20      15.5    9.81  0.1141  0.0809
0.92 - 0.90     321    321    100.0     3.81      11.9    8.14  0.1301  0.1049
0.90 - 0.88     367    367    100.0     3.56      11.8    7.57  0.1447  0.1155
0.88 - 0.87     187    187    100.0     3.25       9.9    6.13  0.1561  0.1462
0.87 - 0.85     413    416     99.3     2.94       9.2    5.42  0.1883  0.1649
0.85 - 0.84     209    222     94.1     2.48       8.0    4.09  0.2738  0.2204
#------------------------------------------------------------------------------
0.94 - 0.84    1811   1827     99.1     3.40      11.4    7.03  0.1474  0.1252
 Inf - 0.84    6463   6482     99.7     4.27      44.4   18.77  0.0471  0.0379
#================================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.4677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3753 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_number_reflns         11517
_refine_ls_number_parameters     883
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.053

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.36392(7) 0.61844(11) 0.51244(6) 0.0274(3) Uani 1 1 d . . . . .
S12 S 0.29030(8) 0.40053(12) 0.40455(7) 0.0371(3) Uani 1 1 d . . . . .
O11 O 0.3725(2) 0.7325(3) 0.54156(18) 0.0360(8) Uani 1 1 d . . . . .
O12 O 0.31326(19) 0.5394(3) 0.53739(17) 0.0344(9) Uani 1 1 d . . . . .
N11 N 0.7130(2) 0.4186(4) 0.5901(2) 0.0341(11) Uani 1 1 d . . . . .
H10 H 0.721380 0.344917 0.603470 0.051 Uiso 1 1 d R U . . .
H11 H 0.757390 0.461117 0.589000 0.051 Uiso 1 1 d R U . . .
N12 N 0.3256(2) 0.6328(4) 0.4216(2) 0.0261(9) Uani 1 1 d . . . . .
N13 N 0.2724(2) 0.5479(4) 0.3030(2) 0.0266(9) Uani 1 1 d . . . . .
H17 H 0.270667 0.612671 0.279421 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6322(3) 0.4660(4) 0.5714(2) 0.0255(11) Uani 1 1 d . . . . .
C12 C 0.6174(3) 0.5819(5) 0.5539(2) 0.0293(11) Uani 1 1 d . . . . .
H12 H 0.663744 0.629138 0.554154 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5362(3) 0.6276(5) 0.5362(2) 0.0277(11) Uani 1 1 d . . . . .
H13 H 0.526805 0.705882 0.523637 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4674(3) 0.5598(4) 0.5368(2) 0.0253(11) Uani 1 1 d . . . . .
C15 C 0.4819(3) 0.4464(4) 0.5561(2) 0.0252(11) Uani 1 1 d . . . . .
H15 H 0.435677 0.400494 0.557557 0.030 Uiso 1 1 calc R U . . .
C16 C 0.5631(3) 0.3988(5) 0.5734(2) 0.0278(11) Uani 1 1 d . . . . .
H16 H 0.572120 0.320781 0.586593 0.033 Uiso 1 1 calc R U . . .
C17 C 0.2986(3) 0.5410(4) 0.3784(2) 0.0241(10) Uani 1 1 d . . . . .
C18 C 0.2484(3) 0.4465(5) 0.2652(3) 0.0342(12) Uani 1 1 d . . . . .
H18 H 0.228966 0.439976 0.211817 0.041 Uiso 1 1 calc R U . . .
C19 C 0.2550(3) 0.3584(5) 0.3107(3) 0.0401(13) Uani 1 1 d . . . . .
H19 H 0.242159 0.282167 0.293996 0.048 Uiso 1 1 calc R U . . .
S21 S 0.85970(7) 0.60767(11) 0.51572(6) 0.0290(3) Uani 1 1 d . . . . .
S22 S 0.76815(8) 0.82199(12) 0.40842(7) 0.0369(3) Uani 1 1 d . . . . .
O21 O 0.8662(2) 0.4936(3) 0.54458(18) 0.0356(8) Uani 1 1 d . . . . .
O22 O 0.8106(2) 0.6876(3) 0.54118(18) 0.0357(9) Uani 1 1 d . . . . .
N21 N 1.2088(2) 0.7974(4) 0.5806(2) 0.0352(11) Uani 1 1 d . . . . .
H20 H 1.215859 0.873185 0.585426 0.053 Uiso 1 1 d R U . . .
H21 H 1.253769 0.752635 0.583686 0.053 Uiso 1 1 d R U . . .
N22 N 0.8224(2) 0.5954(4) 0.4256(2) 0.0274(9) Uani 1 1 d . . . . .
N23 N 0.7607(2) 0.6777(4) 0.3074(2) 0.0294(10) Uani 1 1 d . . . . .
H27 H 0.764507 0.614402 0.284227 0.044 Uiso 1 1 calc R U . . .
C21 C 1.1286(3) 0.7504(5) 0.5680(2) 0.0268(12) Uani 1 1 d . . . . .
C22 C 1.1151(3) 0.6336(5) 0.5626(2) 0.0290(11) Uani 1 1 d . . . . .
H22 H 1.161894 0.583827 0.568258 0.035 Uiso 1 1 calc R U . . .
C23 C 1.0342(3) 0.5897(5) 0.5492(2) 0.0292(11) Uani 1 1 d . . . . .
H23 H 1.025543 0.509772 0.545490 0.035 Uiso 1 1 calc R U . . .
C24 C 0.9651(3) 0.6615(4) 0.5410(2) 0.0252(11) Uani 1 1 d . . . . .
C25 C 0.9792(3) 0.7779(4) 0.5502(2) 0.0257(11) Uani 1 1 d . . . . .
H25 H 0.932954 0.827296 0.547112 0.031 Uiso 1 1 calc R U . . .
C26 C 1.0599(3) 0.8215(5) 0.5637(2) 0.0256(10) Uani 1 1 d . . . . .
H26 H 1.069169 0.901052 0.570129 0.031 Uiso 1 1 calc R U . . .
C27 C 0.7879(3) 0.6857(5) 0.3828(3) 0.0279(11) Uani 1 1 d . . . . .
C28 C 0.7262(3) 0.7765(5) 0.2690(3) 0.0350(12) Uani 1 1 d . . . . .
H28 H 0.705008 0.782653 0.215531 0.042 Uiso 1 1 calc R U . . .
C29 C 0.7257(3) 0.8628(5) 0.3145(3) 0.0407(13) Uani 1 1 d . . . . .
H29 H 0.704676 0.936801 0.297513 0.049 Uiso 1 1 calc R U . . .
S31 S 0.67982(7) 0.64863(11) 0.03588(6) 0.0281(3) Uani 1 1 d . . . . .
S32 S 0.74554(8) 0.39353(12) 0.09530(7) 0.0338(3) Uani 1 1 d . . . . .
O31 O 0.6795(2) 0.7708(3) 0.03194(19) 0.0391(9) Uani 1 1 d . . . . .
O32 O 0.72580(19) 0.5888(3) -0.00504(16) 0.0346(9) Uani 1 1 d . . . . .
N31 N 0.3126(2) 0.5025(4) -0.0983(2) 0.0361(11) Uani 1 1 d . . . . .
H30 H 0.298247 0.437317 -0.124622 0.054 Uiso 1 1 d R U . . .
H31 H 0.271547 0.545267 -0.091152 0.054 Uiso 1 1 d R U . . .
N32 N 0.7132(2) 0.6189(4) 0.1227(2) 0.0266(9) Uani 1 1 d . . . . .
N33 N 0.7730(2) 0.4931(4) 0.2224(2) 0.0269(9) Uani 1 1 d . . . . .
C31 C 0.3985(3) 0.5379(5) -0.0689(2) 0.0266(11) Uani 1 1 d . . . . .
C32 C 0.4213(3) 0.6403(5) -0.0298(3) 0.0286(11) Uani 1 1 d . . . . .
H32 H 0.377896 0.687769 -0.024343 0.034 Uiso 1 1 calc R U . . .
C33 C 0.5067(3) 0.6731(4) 0.0011(3) 0.0272(11) Uani 1 1 d . . . . .
H33 H 0.521789 0.742454 0.028319 0.033 Uiso 1 1 calc R U . . .
C34 C 0.5709(3) 0.6056(4) -0.0074(2) 0.0248(11) Uani 1 1 d . . . . .
C35 C 0.5487(3) 0.5056(4) -0.0484(2) 0.0249(11) Uani 1 1 d . . . . .
H35 H 0.592287 0.459838 -0.055051 0.030 Uiso 1 1 calc R U . . .
C36 C 0.4634(3) 0.4725(4) -0.0794(2) 0.0263(11) Uani 1 1 d . . . . .
H36 H 0.448514 0.404603 -0.108305 0.032 Uiso 1 1 calc R U . . .
C37 C 0.7429(3) 0.5142(5) 0.1487(2) 0.0241(11) Uani 1 1 d . . . . .
C38 C 0.7974(3) 0.3804(5) 0.2369(3) 0.0321(12) Uani 1 1 d . . . . .
H38 H 0.820918 0.351348 0.286928 0.039 Uiso 1 1 calc R U . . .
C39 C 0.7862(3) 0.3145(5) 0.1768(3) 0.0366(13) Uani 1 1 d . . . . .
H39 H 0.798817 0.235626 0.178769 0.044 Uiso 1 1 calc R U . . .
S41 S 0.18050(7) 0.58116(10) 0.02493(6) 0.0264(3) Uani 1 1 d . . . . .
S42 S 0.24387(7) 0.83292(11) 0.08507(6) 0.0311(3) Uani 1 1 d . . . . .
O41 O 0.1793(2) 0.4590(3) 0.01677(19) 0.0387(9) Uani 1 1 d . . . . .
O42 O 0.22279(19) 0.6442(3) -0.01682(17) 0.0316(8) Uani 1 1 d . . . . .
N41 N -0.1854(2) 0.7321(4) -0.0844(2) 0.0339(10) Uani 1 1 d . . . . .
H40 H -0.200981 0.798291 -0.109361 0.051 Uiso 1 1 d R U . . .
H41 H -0.225091 0.689251 -0.075091 0.051 Uiso 1 1 d R U . . .
N42 N 0.2188(2) 0.6060(4) 0.1127(2) 0.0261(9) Uani 1 1 d . . . . .
N43 N 0.2649(2) 0.7362(4) 0.2118(2) 0.0269(9) Uani 1 1 d . . . . .
C41 C -0.1005(3) 0.6960(5) -0.0606(2) 0.0262(11) Uani 1 1 d . . . . .
C42 C -0.0757(3) 0.5923(4) -0.0241(2) 0.0249(11) Uani 1 1 d . . . . .
H42 H -0.117658 0.544894 -0.016197 0.030 Uiso 1 1 calc R U . . .
C43 C 0.0093(3) 0.5576(4) 0.0008(2) 0.0263(11) Uani 1 1 d . . . . .
H43 H 0.025332 0.486884 0.026150 0.032 Uiso 1 1 calc R U . . .
C44 C 0.0719(3) 0.6252(4) -0.0110(2) 0.0229(10) Uani 1 1 d . . . . .
C45 C 0.0474(3) 0.7280(4) -0.0496(2) 0.0249(11) Uani 1 1 d . . . . .
H45 H 0.089189 0.774324 -0.058787 0.030 Uiso 1 1 calc R U . . .
C46 C -0.0383(3) 0.7621(4) -0.0746(2) 0.0245(11) Uani 1 1 d . . . . .
H46 H -0.055004 0.831387 -0.101709 0.029 Uiso 1 1 calc R U . . .
C47 C 0.2408(3) 0.7133(4) 0.1387(2) 0.0237(11) Uani 1 1 d . . . . .
C48 C 0.2838(3) 0.8494(5) 0.2257(3) 0.0333(12) Uani 1 1 d . . . . .
H48 H 0.302034 0.880144 0.275255 0.040 Uiso 1 1 calc R U . . .
C49 C 0.2752(3) 0.9142(5) 0.1654(3) 0.0349(12) Uani 1 1 d . . . . .
H49 H 0.285135 0.993815 0.166964 0.042 Uiso 1 1 calc R U . . .
N51 N 0.5111(2) 0.4808(4) 0.27991(19) 0.0236(9) Uani 1 1 d . . . . .
N52 N 0.4415(2) 0.2934(3) 0.20482(19) 0.0233(9) Uani 1 1 d . . . . .
H52 H 0.453467 0.334528 0.253565 0.035 Uiso 1 1 calc R U . . .
C51 C 0.4524(3) 0.5482(4) 0.2152(2) 0.0264(10) Uani 1 1 d . . . . .
H51A H 0.396194 0.554020 0.222587 0.032 Uiso 1 1 calc R U . . .
C52 C 0.4834(3) 0.6694(5) 0.2133(3) 0.0329(12) Uani 1 1 d . . . . .
H52A H 0.439147 0.712013 0.172335 0.040 Uiso 1 1 calc R U . . .
H52B H 0.537050 0.668249 0.202548 0.040 Uiso 1 1 calc R U . . .
C53 C 0.5005(3) 0.7296(5) 0.2888(3) 0.0366(12) Uani 1 1 d . . . . .
H53A H 0.526764 0.804858 0.288247 0.044 Uiso 1 1 calc R U . . .
H53B H 0.445166 0.741762 0.295760 0.044 Uiso 1 1 calc R U . . .
C54 C 0.5604(3) 0.6598(5) 0.3539(3) 0.0340(12) Uani 1 1 d . . . . .
H54A H 0.565846 0.696569 0.402142 0.041 Uiso 1 1 calc R U . . .
H54B H 0.618430 0.657640 0.350953 0.041 Uiso 1 1 calc R U . . .
C55 C 0.5275(3) 0.5389(5) 0.3528(3) 0.0306(11) Uani 1 1 d . . . . .
H55A H 0.570497 0.494792 0.393730 0.037 Uiso 1 1 calc R U . . .
H55B H 0.473315 0.540770 0.362795 0.037 Uiso 1 1 calc R U . . .
C56 C 0.5929(3) 0.4494(4) 0.2694(2) 0.0272(10) Uani 1 1 d . . . . .
H56A H 0.630196 0.404601 0.313349 0.033 Uiso 1 1 calc R U . . .
H56B H 0.624547 0.519088 0.266137 0.033 Uiso 1 1 calc R U . . .
C57 C 0.5721(3) 0.3794(4) 0.1971(2) 0.0261(10) Uani 1 1 d . . . . .
H57A H 0.627699 0.362119 0.190709 0.031 Uiso 1 1 calc R U . . .
C58 C 0.5173(3) 0.4521(4) 0.1304(2) 0.0310(11) Uani 1 1 d . . . . .
H58A H 0.548614 0.522645 0.128007 0.037 Uiso 1 1 calc R U . . .
H58B H 0.504498 0.409897 0.082540 0.037 Uiso 1 1 calc R U . . .
C59 C 0.4340(3) 0.4808(4) 0.1418(2) 0.0275(11) Uani 1 1 d . . . . .
H59A H 0.396964 0.528057 0.098350 0.033 Uiso 1 1 calc R U . . .
C60 C 0.3870(3) 0.3701(4) 0.1424(2) 0.0297(11) Uani 1 1 d . . . . .
H60A H 0.332182 0.386886 0.149343 0.036 Uiso 1 1 calc R U . . .
H60B H 0.372817 0.331046 0.093314 0.036 Uiso 1 1 calc R U . . .
C61 C 0.3931(3) 0.1863(4) 0.2074(3) 0.0325(11) Uani 1 1 d . . . . .
H61A H 0.337898 0.206011 0.212767 0.039 Uiso 1 1 calc R U . . .
H61B H 0.379714 0.143508 0.159730 0.039 Uiso 1 1 calc R U . . .
C62 C 0.4466(3) 0.1137(5) 0.2729(2) 0.0347(12) Uani 1 1 d . . . . .
H62A H 0.414064 0.043918 0.274443 0.042 Uiso 1 1 calc R U . . .
H62B H 0.458006 0.155692 0.320661 0.042 Uiso 1 1 calc R U . . .
C63 C 0.5318(3) 0.0812(5) 0.2664(3) 0.0358(12) Uani 1 1 d . . . . .
H63A H 0.566988 0.035891 0.310964 0.043 Uiso 1 1 calc R U . . .
H63B H 0.521023 0.034558 0.220631 0.043 Uiso 1 1 calc R U . . .
C64 C 0.5797(3) 0.1887(5) 0.2619(3) 0.0345(11) Uani 1 1 d . . . . .
H64A H 0.633606 0.167653 0.254673 0.041 Uiso 1 1 calc R U . . .
H64B H 0.596065 0.229811 0.310571 0.041 Uiso 1 1 calc R U . . .
C65 C 0.5277(3) 0.2682(4) 0.1984(2) 0.0252(11) Uani 1 1 d . . . . .
H65A H 0.516461 0.228615 0.149306 0.030 Uiso 1 1 calc R U . . .
N71 N 1.0216(2) 0.7391(4) 0.2874(2) 0.0258(9) Uani 1 1 d . . . . .
N72 N 1.0342(2) 0.9273(3) 0.2127(2) 0.0248(9) Uani 1 1 d . . . . .
H72 H 1.058141 0.891178 0.263783 0.037 Uiso 1 1 calc R U . . .
C71 C 1.0417(3) 0.6710(4) 0.2298(2) 0.0260(10) Uani 1 1 d . . . . .
H71A H 1.105987 0.668812 0.246075 0.031 Uiso 1 1 calc R U . . .
C72 C 1.0107(3) 0.5473(5) 0.2243(3) 0.0345(12) Uani 1 1 d . . . . .
H72A H 0.946825 0.545421 0.204177 0.041 Uiso 1 1 calc R U . . .
H72B H 1.030738 0.504947 0.188954 0.041 Uiso 1 1 calc R U . . .
C73 C 1.0457(3) 0.4907(5) 0.3020(3) 0.0385(12) Uani 1 1 d . . . . .
H73A H 1.019532 0.414458 0.298642 0.046 Uiso 1 1 calc R U . . .
H73B H 1.108942 0.481060 0.318100 0.046 Uiso 1 1 calc R U . . .
C74 C 1.0258(4) 0.5612(5) 0.3602(3) 0.0432(13) Uani 1 1 d . . . . .
H74A H 0.962750 0.560831 0.348394 0.052 Uiso 1 1 calc R U . . .
H74B H 1.054411 0.526860 0.410799 0.052 Uiso 1 1 calc R U . . .
C75 C 1.0565(4) 0.6827(5) 0.3614(3) 0.0392(13) Uani 1 1 d . . . . .
H75A H 1.039589 0.726907 0.397927 0.047 Uiso 1 1 calc R U . . .
H75B H 1.120328 0.683071 0.379378 0.047 Uiso 1 1 calc R U . . .
C76 C 0.9281(3) 0.7621(4) 0.2631(3) 0.0337(11) Uani 1 1 d . . . . .
H76A H 0.916869 0.807542 0.302275 0.040 Uiso 1 1 calc R U . . .
H76B H 0.896364 0.689422 0.257267 0.040 Uiso 1 1 calc R U . . .
C77 C 0.8955(3) 0.8270(5) 0.1879(3) 0.0357(11) Uani 1 1 d . . . . .
H77A H 0.831883 0.838784 0.172528 0.043 Uiso 1 1 calc R U . . .
C78 C 0.9108(3) 0.7551(5) 0.1283(3) 0.0360(12) Uani 1 1 d . . . . .
H78A H 0.889683 0.795197 0.079123 0.043 Uiso 1 1 calc R U . . .
H78B H 0.879509 0.682082 0.122275 0.043 Uiso 1 1 calc R U . . .
C79 C 1.0069(3) 0.7341(4) 0.1538(2) 0.0297(11) Uani 1 1 d . . . . .
H79A H 1.017881 0.686177 0.114944 0.036 Uiso 1 1 calc R U . . .
C80 C 1.0516(3) 0.8480(4) 0.1580(3) 0.0331(11) Uani 1 1 d . . . . .
H80A H 1.114627 0.835712 0.174113 0.040 Uiso 1 1 calc R U . . .
H80B H 1.031037 0.883230 0.107292 0.040 Uiso 1 1 calc R U . . .
C81 C 1.0809(3) 1.0368(4) 0.2172(3) 0.0353(11) Uani 1 1 d . . . . .
H81A H 1.061719 1.071844 0.166383 0.042 Uiso 1 1 calc R U . . .
H81B H 1.143649 1.021725 0.233734 0.042 Uiso 1 1 calc R U . . .
C82 C 1.0647(3) 1.1186(5) 0.2717(3) 0.0416(13) Uani 1 1 d . . . . .
H82A H 1.090366 1.087688 0.323617 0.050 Uiso 1 1 calc R U . . .
H82B H 1.093098 1.192034 0.270620 0.050 Uiso 1 1 calc R U . . .
C83 C 0.9693(3) 1.1380(5) 0.2520(3) 0.0410(13) Uani 1 1 d . . . . .
H83A H 0.944428 1.176529 0.202469 0.049 Uiso 1 1 calc R U . . .
H83B H 0.960370 1.187514 0.290492 0.049 Uiso 1 1 calc R U . . .
C84 C 0.9240(3) 1.0242(5) 0.2489(3) 0.0392(12) Uani 1 1 d . . . . .
H84A H 0.946011 0.989034 0.299647 0.047 Uiso 1 1 calc R U . . .
H84B H 0.861329 1.037392 0.234481 0.047 Uiso 1 1 calc R U . . .
C85 C 0.9384(3) 0.9440(4) 0.1931(3) 0.0279(11) Uani 1 1 d . . . . .
H85A H 0.914058 0.980179 0.142070 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 O11 1.440(4) . ?
S11 O12 1.450(3) . ?
S11 N12 1.618(4) . ?
S11 C14 1.755(5) . ?
S12 C19 1.736(5) . ?
S12 C17 1.747(5) . ?
N11 C11 1.378(6) . ?
N11 H10 0.9000 . ?
N11 H11 0.9000 . ?
N12 C17 1.332(6) . ?
N13 C17 1.342(5) . ?
N13 C18 1.375(6) . ?
N13 H17 0.8800 . ?
C11 C12 1.404(7) . ?
C11 C16 1.410(6) . ?
C12 C13 1.379(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(7) . ?
C15 C16 1.388(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.330(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
S21 O21 1.440(4) . ?
S21 O22 1.444(3) . ?
S21 N22 1.603(4) . ?
S21 C24 1.760(5) . ?
S22 C29 1.732(5) . ?
S22 C27 1.743(5) . ?
N21 C21 1.384(6) . ?
N21 H20 0.9000 . ?
N21 H21 0.9000 . ?
N22 C27 1.334(6) . ?
N23 C27 1.341(6) . ?
N23 C28 1.382(6) . ?
N23 H27 0.8800 . ?
C21 C22 1.391(7) . ?
C21 C26 1.395(6) . ?
C22 C23 1.377(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(7) . ?
C25 C26 1.373(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C28 C29 1.338(7) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
S31 O31 1.440(4) . ?
S31 O32 1.461(3) . ?
S31 N32 1.579(4) . ?
S31 C34 1.769(4) . ?
S32 C39 1.719(5) . ?
S32 C37 1.758(5) . ?
N31 C31 1.394(6) . ?
N31 H30 0.9000 . ?
N31 H31 0.9000 . ?
N32 C37 1.353(6) . ?
N33 C37 1.327(5) . ?
N33 C38 1.386(7) . ?
C31 C32 1.395(7) . ?
C31 C36 1.403(6) . ?
C32 C33 1.379(7) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(7) . ?
C35 C36 1.379(6) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C38 C39 1.339(7) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
S41 O41 1.445(4) . ?
S41 O42 1.448(3) . ?
S41 N42 1.581(4) . ?
S41 C44 1.761(4) . ?
S42 C49 1.715(5) . ?
S42 C47 1.752(5) . ?
N41 C41 1.384(6) . ?
N41 H40 0.9001 . ?
N41 H41 0.9000 . ?
N42 C47 1.358(6) . ?
N43 C47 1.326(5) . ?
N43 C48 1.373(7) . ?
C41 C42 1.390(7) . ?
C41 C46 1.400(6) . ?
C42 C43 1.379(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.395(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.397(7) . ?
C45 C46 1.389(6) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C48 C49 1.343(7) . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
N51 C55 1.480(6) . ?
N51 C51 1.489(6) . ?
N51 C56 1.497(5) . ?
N52 C60 1.501(6) . ?
N52 C61 1.508(6) . ?
N52 C65 1.516(5) . ?
N52 H52 1.0000 . ?
C51 C52 1.523(7) . ?
C51 C59 1.536(6) . ?
C51 H51A 1.0000 . ?
C52 C53 1.532(7) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.515(7) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 C55 1.523(7) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 C57 1.531(6) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C57 C65 1.509(7) . ?
C57 C58 1.525(6) . ?
C57 H57A 1.0000 . ?
C58 C59 1.522(6) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C60 1.523(7) . ?
C59 H59A 1.0000 . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 C62 1.504(7) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 C63 1.521(6) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.516(7) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 C65 1.522(7) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 H65A 1.0000 . ?
N71 C75 1.471(6) . ?
N71 C76 1.479(5) . ?
N71 C71 1.494(6) . ?
N72 C81 1.492(6) . ?
N72 C80 1.505(6) . ?
N72 C85 1.514(5) . ?
N72 H72 1.0000 . ?
C71 C72 1.535(7) . ?
C71 C79 1.538(6) . ?
C71 H71A 1.0000 . ?
C72 C73 1.529(7) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C73 C74 1.518(7) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C74 C75 1.517(7) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 H75A 0.9900 . ?
C75 H75B 0.9900 . ?
C76 C77 1.536(7) . ?
C76 H76A 0.9900 . ?
C76 H76B 0.9900 . ?
C77 C78 1.512(7) . ?
C77 C85 1.538(7) . ?
C77 H77A 1.0000 . ?
C78 C79 1.514(6) . ?
C78 H78A 0.9900 . ?
C78 H78B 0.9900 . ?
C79 C80 1.522(7) . ?
C79 H79A 1.0000 . ?
C80 H80A 0.9900 . ?
C80 H80B 0.9900 . ?
C81 C82 1.514(7) . ?
C81 H81A 0.9900 . ?
C81 H81B 0.9900 . ?
C82 C83 1.510(7) . ?
C82 H82A 0.9900 . ?
C82 H82B 0.9900 . ?
C83 C84 1.528(8) . ?
C83 H83A 0.9900 . ?
C83 H83B 0.9900 . ?
C84 C85 1.506(7) . ?
C84 H84A 0.9900 . ?
C84 H84B 0.9900 . ?
C85 H85A 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S11 O12 117.3(2) . . ?
O11 S11 N12 105.0(2) . . ?
O12 S11 N12 111.8(2) . . ?
O11 S11 C14 108.5(2) . . ?
O12 S11 C14 107.3(2) . . ?
N12 S11 C14 106.6(2) . . ?
C19 S12 C17 90.5(3) . . ?
C11 N11 H10 119.9 . . ?
C11 N11 H11 120.1 . . ?
H10 N11 H11 120.0 . . ?
C17 N12 S11 119.1(3) . . ?
C17 N13 C18 115.2(4) . . ?
C17 N13 H17 122.4 . . ?
C18 N13 H17 122.4 . . ?
N11 C11 C12 121.6(4) . . ?
N11 C11 C16 119.8(5) . . ?
C12 C11 C16 118.6(4) . . ?
C13 C12 C11 120.5(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.6(5) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 S11 120.5(4) . . ?
C13 C14 S11 120.1(4) . . ?
C14 C15 C16 120.8(4) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.2(5) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N12 C17 N13 121.0(4) . . ?
N12 C17 S12 129.5(3) . . ?
N13 C17 S12 109.5(4) . . ?
C19 C18 N13 113.4(4) . . ?
C19 C18 H18 123.3 . . ?
N13 C18 H18 123.3 . . ?
C18 C19 S12 111.4(4) . . ?
C18 C19 H19 124.3 . . ?
S12 C19 H19 124.3 . . ?
O21 S21 O22 116.8(2) . . ?
O21 S21 N22 105.6(2) . . ?
O22 S21 N22 112.1(2) . . ?
O21 S21 C24 107.8(2) . . ?
O22 S21 C24 107.8(2) . . ?
N22 S21 C24 106.20(19) . . ?
C29 S22 C27 90.7(3) . . ?
C21 N21 H20 119.6 . . ?
C21 N21 H21 120.4 . . ?
H20 N21 H21 120.0 . . ?
C27 N22 S21 119.4(3) . . ?
C27 N23 C28 114.7(4) . . ?
C27 N23 H27 122.7 . . ?
C28 N23 H27 122.7 . . ?
N21 C21 C22 121.9(4) . . ?
N21 C21 C26 119.4(5) . . ?
C22 C21 C26 118.7(4) . . ?
C23 C22 C21 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.4(5) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 119.4(4) . . ?
C25 C24 S21 119.6(4) . . ?
C23 C24 S21 120.9(4) . . ?
C26 C25 C24 120.0(4) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.9(5) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
N22 C27 N23 119.8(4) . . ?
N22 C27 S22 130.2(4) . . ?
N23 C27 S22 110.0(4) . . ?
C29 C28 N23 113.4(5) . . ?
C29 C28 H28 123.3 . . ?
N23 C28 H28 123.3 . . ?
C28 C29 S22 111.2(4) . . ?
C28 C29 H29 124.4 . . ?
S22 C29 H29 124.4 . . ?
O31 S31 O32 116.5(2) . . ?
O31 S31 N32 105.6(2) . . ?
O32 S31 N32 113.71(19) . . ?
O31 S31 C34 106.2(2) . . ?
O32 S31 C34 105.3(2) . . ?
N32 S31 C34 109.2(2) . . ?
C39 S32 C37 90.0(3) . . ?
C31 N31 H30 120.1 . . ?
C31 N31 H31 119.9 . . ?
H30 N31 H31 120.0 . . ?
C37 N32 S31 121.7(3) . . ?
C37 N33 C38 111.0(4) . . ?
N31 C31 C32 120.7(4) . . ?
N31 C31 C36 120.8(5) . . ?
C32 C31 C36 118.6(4) . . ?
C33 C32 C31 120.3(4) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 120.6(5) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C35 C34 C33 119.7(4) . . ?
C35 C34 S31 121.3(3) . . ?
C33 C34 S31 119.0(4) . . ?
C36 C35 C34 120.0(4) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.8(5) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
N33 C37 N32 120.1(4) . . ?
N33 C37 S32 112.4(4) . . ?
N32 C37 S32 127.5(3) . . ?
C39 C38 N33 116.4(4) . . ?
C39 C38 H38 121.8 . . ?
N33 C38 H38 121.8 . . ?
C38 C39 S32 110.1(4) . . ?
C38 C39 H39 124.9 . . ?
S32 C39 H39 124.9 . . ?
O41 S41 O42 116.2(2) . . ?
O41 S41 N42 106.4(2) . . ?
O42 S41 N42 113.5(2) . . ?
O41 S41 C44 106.2(2) . . ?
O42 S41 C44 106.0(2) . . ?
N42 S41 C44 108.16(19) . . ?
C49 S42 C47 89.6(2) . . ?
C41 N41 H40 119.9 . . ?
C41 N41 H41 120.1 . . ?
H40 N41 H41 120.0 . . ?
C47 N42 S41 120.5(3) . . ?
C47 N43 C48 111.0(4) . . ?
N41 C41 C42 120.9(4) . . ?
N41 C41 C46 120.5(5) . . ?
C42 C41 C46 118.6(4) . . ?
C43 C42 C41 120.7(4) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C42 C43 C44 120.7(5) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C43 C44 C45 119.3(4) . . ?
C43 C44 S41 119.5(4) . . ?
C45 C44 S41 121.2(3) . . ?
C46 C45 C44 119.6(4) . . ?
C46 C45 H45 120.2 . . ?
C44 C45 H45 120.2 . . ?
C45 C46 C41 121.0(5) . . ?
C45 C46 H46 119.5 . . ?
C41 C46 H46 119.5 . . ?
N43 C47 N42 120.6(4) . . ?
N43 C47 S42 112.8(4) . . ?
N42 C47 S42 126.6(3) . . ?
C49 C48 N43 116.2(5) . . ?
C49 C48 H48 121.9 . . ?
N43 C48 H48 121.9 . . ?
C48 C49 S42 110.4(4) . . ?
C48 C49 H49 124.8 . . ?
S42 C49 H49 124.8 . . ?
C55 N51 C51 111.6(4) . . ?
C55 N51 C56 112.2(3) . . ?
C51 N51 C56 111.9(3) . . ?
C60 N52 C61 110.7(3) . . ?
C60 N52 C65 111.6(3) . . ?
C61 N52 C65 112.0(4) . . ?
C60 N52 H52 107.4 . . ?
C61 N52 H52 107.4 . . ?
C65 N52 H52 107.4 . . ?
N51 C51 C52 113.2(4) . . ?
N51 C51 C59 109.1(4) . . ?
C52 C51 C59 114.7(4) . . ?
N51 C51 H51A 106.4 . . ?
C52 C51 H51A 106.4 . . ?
C59 C51 H51A 106.4 . . ?
C51 C52 C53 111.0(4) . . ?
C51 C52 H52A 109.4 . . ?
C53 C52 H52A 109.4 . . ?
C51 C52 H52B 109.4 . . ?
C53 C52 H52B 109.4 . . ?
H52A C52 H52B 108.0 . . ?
C54 C53 C52 110.8(4) . . ?
C54 C53 H53A 109.5 . . ?
C52 C53 H53A 109.5 . . ?
C54 C53 H53B 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 108.1 . . ?
C53 C54 C55 111.7(4) . . ?
C53 C54 H54A 109.3 . . ?
C55 C54 H54A 109.3 . . ?
C53 C54 H54B 109.3 . . ?
C55 C54 H54B 109.3 . . ?
H54A C54 H54B 107.9 . . ?
N51 C55 C54 112.7(4) . . ?
N51 C55 H55A 109.1 . . ?
C54 C55 H55A 109.1 . . ?
N51 C55 H55B 109.1 . . ?
C54 C55 H55B 109.1 . . ?
H55A C55 H55B 107.8 . . ?
N51 C56 C57 109.8(3) . . ?
N51 C56 H56A 109.7 . . ?
C57 C56 H56A 109.7 . . ?
N51 C56 H56B 109.7 . . ?
C57 C56 H56B 109.7 . . ?
H56A C56 H56B 108.2 . . ?
C65 C57 C58 110.7(4) . . ?
C65 C57 C56 113.6(4) . . ?
C58 C57 C56 108.4(4) . . ?
C65 C57 H57A 108.0 . . ?
C58 C57 H57A 108.0 . . ?
C56 C57 H57A 108.0 . . ?
C59 C58 C57 107.5(3) . . ?
C59 C58 H58A 110.2 . . ?
C57 C58 H58A 110.2 . . ?
C59 C58 H58B 110.2 . . ?
C57 C58 H58B 110.2 . . ?
H58A C58 H58B 108.5 . . ?
C58 C59 C60 108.2(4) . . ?
C58 C59 C51 111.1(4) . . ?
C60 C59 C51 111.4(4) . . ?
C58 C59 H59A 108.7 . . ?
C60 C59 H59A 108.7 . . ?
C51 C59 H59A 108.7 . . ?
N52 C60 C59 110.9(3) . . ?
N52 C60 H60A 109.5 . . ?
C59 C60 H60A 109.5 . . ?
N52 C60 H60B 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 108.0 . . ?
C62 C61 N52 110.0(4) . . ?
C62 C61 H61A 109.7 . . ?
N52 C61 H61A 109.7 . . ?
C62 C61 H61B 109.7 . . ?
N52 C61 H61B 109.7 . . ?
H61A C61 H61B 108.2 . . ?
C61 C62 C63 111.1(4) . . ?
C61 C62 H62A 109.4 . . ?
C63 C62 H62A 109.4 . . ?
C61 C62 H62B 109.4 . . ?
C63 C62 H62B 109.4 . . ?
H62A C62 H62B 108.0 . . ?
C64 C63 C62 108.8(4) . . ?
C64 C63 H63A 109.9 . . ?
C62 C63 H63A 109.9 . . ?
C64 C63 H63B 109.9 . . ?
C62 C63 H63B 109.9 . . ?
H63A C63 H63B 108.3 . . ?
C63 C64 C65 113.6(4) . . ?
C63 C64 H64A 108.8 . . ?
C65 C64 H64A 108.8 . . ?
C63 C64 H64B 108.8 . . ?
C65 C64 H64B 108.8 . . ?
H64A C64 H64B 107.7 . . ?
C57 C65 N52 108.5(4) . . ?
C57 C65 C64 114.0(4) . . ?
N52 C65 C64 109.6(3) . . ?
C57 C65 H65A 108.2 . . ?
N52 C65 H65A 108.2 . . ?
C64 C65 H65A 108.2 . . ?
C75 N71 C76 112.3(3) . . ?
C75 N71 C71 110.3(4) . . ?
C76 N71 C71 111.5(3) . . ?
C81 N72 C80 110.1(3) . . ?
C81 N72 C85 112.5(4) . . ?
C80 N72 C85 111.5(3) . . ?
C81 N72 H72 107.5 . . ?
C80 N72 H72 107.5 . . ?
C85 N72 H72 107.5 . . ?
N71 C71 C72 113.5(4) . . ?
N71 C71 C79 108.9(4) . . ?
C72 C71 C79 113.1(4) . . ?
N71 C71 H71A 107.0 . . ?
C72 C71 H71A 107.0 . . ?
C79 C71 H71A 107.0 . . ?
C73 C72 C71 110.4(4) . . ?
C73 C72 H72A 109.6 . . ?
C71 C72 H72A 109.6 . . ?
C73 C72 H72B 109.6 . . ?
C71 C72 H72B 109.6 . . ?
H72A C72 H72B 108.1 . . ?
C74 C73 C72 111.2(4) . . ?
C74 C73 H73A 109.4 . . ?
C72 C73 H73A 109.4 . . ?
C74 C73 H73B 109.4 . . ?
C72 C73 H73B 109.4 . . ?
H73A C73 H73B 108.0 . . ?
C75 C74 C73 111.2(4) . . ?
C75 C74 H74A 109.4 . . ?
C73 C74 H74A 109.4 . . ?
C75 C74 H74B 109.4 . . ?
C73 C74 H74B 109.4 . . ?
H74A C74 H74B 108.0 . . ?
N71 C75 C74 113.6(4) . . ?
N71 C75 H75A 108.9 . . ?
C74 C75 H75A 108.9 . . ?
N71 C75 H75B 108.9 . . ?
C74 C75 H75B 108.9 . . ?
H75A C75 H75B 107.7 . . ?
N71 C76 C77 110.5(3) . . ?
N71 C76 H76A 109.5 . . ?
C77 C76 H76A 109.5 . . ?
N71 C76 H76B 109.5 . . ?
C77 C76 H76B 109.5 . . ?
H76A C76 H76B 108.1 . . ?
C78 C77 C76 108.9(4) . . ?
C78 C77 C85 110.2(4) . . ?
C76 C77 C85 112.9(4) . . ?
C78 C77 H77A 108.2 . . ?
C76 C77 H77A 108.2 . . ?
C85 C77 H77A 108.2 . . ?
C77 C78 C79 107.6(4) . . ?
C77 C78 H78A 110.2 . . ?
C79 C78 H78A 110.2 . . ?
C77 C78 H78B 110.2 . . ?
C79 C78 H78B 110.2 . . ?
H78A C78 H78B 108.5 . . ?
C78 C79 C80 108.2(4) . . ?
C78 C79 C71 111.5(4) . . ?
C80 C79 C71 111.6(4) . . ?
C78 C79 H79A 108.4 . . ?
C80 C79 H79A 108.4 . . ?
C71 C79 H79A 108.4 . . ?
N72 C80 C79 111.5(3) . . ?
N72 C80 H80A 109.3 . . ?
C79 C80 H80A 109.3 . . ?
N72 C80 H80B 109.3 . . ?
C79 C80 H80B 109.3 . . ?
H80A C80 H80B 108.0 . . ?
N72 C81 C82 111.4(4) . . ?
N72 C81 H81A 109.3 . . ?
C82 C81 H81A 109.3 . . ?
N72 C81 H81B 109.3 . . ?
C82 C81 H81B 109.3 . . ?
H81A C81 H81B 108.0 . . ?
C83 C82 C81 111.4(4) . . ?
C83 C82 H82A 109.3 . . ?
C81 C82 H82A 109.3 . . ?
C83 C82 H82B 109.3 . . ?
C81 C82 H82B 109.3 . . ?
H82A C82 H82B 108.0 . . ?
C82 C83 C84 109.7(4) . . ?
C82 C83 H83A 109.7 . . ?
C84 C83 H83A 109.7 . . ?
C82 C83 H83B 109.7 . . ?
C84 C83 H83B 109.7 . . ?
H83A C83 H83B 108.2 . . ?
C85 C84 C83 111.8(4) . . ?
C85 C84 H84A 109.2 . . ?
C83 C84 H84A 109.2 . . ?
C85 C84 H84B 109.2 . . ?
C83 C84 H84B 109.2 . . ?
H84A C84 H84B 107.9 . . ?
C84 C85 N72 109.6(4) . . ?
C84 C85 C77 114.6(4) . . ?
N72 C85 C77 108.8(4) . . ?
C84 C85 H85A 107.9 . . ?
N72 C85 H85A 107.9 . . ?
C77 C85 H85A 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 N12 C17 -170.3(3) . . . . ?
O12 S11 N12 C17 -42.1(4) . . . . ?
C14 S11 N12 C17 74.8(4) . . . . ?
N11 C11 C12 C13 -179.1(4) . . . . ?
C16 C11 C12 C13 -2.4(6) . . . . ?
C11 C12 C13 C14 1.1(7) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C12 C13 C14 S11 -178.7(3) . . . . ?
O11 S11 C14 C15 143.2(4) . . . . ?
O12 S11 C14 C15 15.6(4) . . . . ?
N12 S11 C14 C15 -104.2(4) . . . . ?
O11 S11 C14 C13 -37.2(4) . . . . ?
O12 S11 C14 C13 -164.8(3) . . . . ?
N12 S11 C14 C13 75.3(4) . . . . ?
C13 C14 C15 C16 -1.3(7) . . . . ?
S11 C14 C15 C16 178.2(3) . . . . ?
C14 C15 C16 C11 0.0(7) . . . . ?
N11 C11 C16 C15 178.7(4) . . . . ?
C12 C11 C16 C15 1.9(6) . . . . ?
S11 N12 C17 N13 -175.0(3) . . . . ?
S11 N12 C17 S12 5.1(6) . . . . ?
C18 N13 C17 N12 178.3(4) . . . . ?
C18 N13 C17 S12 -1.8(4) . . . . ?
C19 S12 C17 N12 -178.1(4) . . . . ?
C19 S12 C17 N13 2.0(3) . . . . ?
C17 N13 C18 C19 0.4(6) . . . . ?
N13 C18 C19 S12 1.2(5) . . . . ?
C17 S12 C19 C18 -1.9(4) . . . . ?
O21 S21 N22 C27 162.4(3) . . . . ?
O22 S21 N22 C27 34.1(4) . . . . ?
C24 S21 N22 C27 -83.4(4) . . . . ?
N21 C21 C22 C23 -179.3(4) . . . . ?
C26 C21 C22 C23 3.5(7) . . . . ?
C21 C22 C23 C24 -0.2(7) . . . . ?
C22 C23 C24 C25 -3.1(7) . . . . ?
C22 C23 C24 S21 174.4(3) . . . . ?
O21 S21 C24 C25 -152.6(4) . . . . ?
O22 S21 C24 C25 -25.7(4) . . . . ?
N22 S21 C24 C25 94.6(4) . . . . ?
O21 S21 C24 C23 29.9(4) . . . . ?
O22 S21 C24 C23 156.8(4) . . . . ?
N22 S21 C24 C23 -82.9(4) . . . . ?
C23 C24 C25 C26 3.0(7) . . . . ?
S21 C24 C25 C26 -174.5(3) . . . . ?
C24 C25 C26 C21 0.3(7) . . . . ?
N21 C21 C26 C25 179.1(4) . . . . ?
C22 C21 C26 C25 -3.6(7) . . . . ?
S21 N22 C27 N23 176.5(3) . . . . ?
S21 N22 C27 S22 -5.1(6) . . . . ?
C28 N23 C27 N22 180.0(4) . . . . ?
C28 N23 C27 S22 1.3(4) . . . . ?
C29 S22 C27 N22 -179.8(4) . . . . ?
C29 S22 C27 N23 -1.3(3) . . . . ?
C27 N23 C28 C29 -0.5(6) . . . . ?
N23 C28 C29 S22 -0.5(5) . . . . ?
C27 S22 C29 C28 1.0(4) . . . . ?
O31 S31 N32 C37 -162.5(3) . . . . ?
O32 S31 N32 C37 -33.6(4) . . . . ?
C34 S31 N32 C37 83.6(4) . . . . ?
N31 C31 C32 C33 178.1(4) . . . . ?
C36 C31 C32 C33 -3.3(7) . . . . ?
C31 C32 C33 C34 1.1(7) . . . . ?
C32 C33 C34 C35 1.2(7) . . . . ?
C32 C33 C34 S31 -177.8(3) . . . . ?
O31 S31 C34 C35 145.9(4) . . . . ?
O32 S31 C34 C35 21.8(4) . . . . ?
N32 S31 C34 C35 -100.6(4) . . . . ?
O31 S31 C34 C33 -35.1(4) . . . . ?
O32 S31 C34 C33 -159.2(3) . . . . ?
N32 S31 C34 C33 78.4(4) . . . . ?
C33 C34 C35 C36 -1.1(6) . . . . ?
S31 C34 C35 C36 177.9(3) . . . . ?
C34 C35 C36 C31 -1.3(7) . . . . ?
N31 C31 C36 C35 -178.0(4) . . . . ?
C32 C31 C36 C35 3.5(7) . . . . ?
C38 N33 C37 N32 178.0(4) . . . . ?
C38 N33 C37 S32 -0.8(4) . . . . ?
S31 N32 C37 N33 177.9(3) . . . . ?
S31 N32 C37 S32 -3.5(5) . . . . ?
C39 S32 C37 N33 1.4(3) . . . . ?
C39 S32 C37 N32 -177.2(4) . . . . ?
C37 N33 C38 C39 -0.6(6) . . . . ?
N33 C38 C39 S32 1.7(5) . . . . ?
C37 S32 C39 C38 -1.7(4) . . . . ?
O41 S41 N42 C47 169.6(3) . . . . ?
O42 S41 N42 C47 40.7(4) . . . . ?
C44 S41 N42 C47 -76.6(4) . . . . ?
N41 C41 C42 C43 -178.9(4) . . . . ?
C46 C41 C42 C43 2.9(6) . . . . ?
C41 C42 C43 C44 -0.8(7) . . . . ?
C42 C43 C44 C45 -1.2(6) . . . . ?
C42 C43 C44 S41 177.3(3) . . . . ?
O41 S41 C44 C43 36.8(4) . . . . ?
O42 S41 C44 C43 160.9(3) . . . . ?
N42 S41 C44 C43 -77.1(4) . . . . ?
O41 S41 C44 C45 -144.7(4) . . . . ?
O42 S41 C44 C45 -20.6(4) . . . . ?
N42 S41 C44 C45 101.4(4) . . . . ?
C43 C44 C45 C46 1.0(6) . . . . ?
S41 C44 C45 C46 -177.5(3) . . . . ?
C44 C45 C46 C41 1.1(6) . . . . ?
N41 C41 C46 C45 178.7(4) . . . . ?
C42 C41 C46 C45 -3.1(6) . . . . ?
C48 N43 C47 N42 -179.7(4) . . . . ?
C48 N43 C47 S42 1.6(5) . . . . ?
S41 N42 C47 N43 173.3(3) . . . . ?
S41 N42 C47 S42 -8.1(5) . . . . ?
C49 S42 C47 N43 -2.0(3) . . . . ?
C49 S42 C47 N42 179.4(4) . . . . ?
C47 N43 C48 C49 -0.2(6) . . . . ?
N43 C48 C49 S42 -1.3(5) . . . . ?
C47 S42 C49 C48 1.8(4) . . . . ?
C55 N51 C51 C52 53.9(5) . . . . ?
C56 N51 C51 C52 -72.8(5) . . . . ?
C55 N51 C51 C59 -177.0(3) . . . . ?
C56 N51 C51 C59 56.3(4) . . . . ?
N51 C51 C52 C53 -53.5(5) . . . . ?
C59 C51 C52 C53 -179.7(4) . . . . ?
C51 C52 C53 C54 52.8(5) . . . . ?
C52 C53 C54 C55 -53.4(5) . . . . ?
C51 N51 C55 C54 -53.9(5) . . . . ?
C56 N51 C55 C54 72.6(5) . . . . ?
C53 C54 C55 N51 54.5(5) . . . . ?
C55 N51 C56 C57 174.4(4) . . . . ?
C51 N51 C56 C57 -59.2(5) . . . . ?
N51 C56 C57 C65 -62.3(5) . . . . ?
N51 C56 C57 C58 61.3(5) . . . . ?
C65 C57 C58 C59 63.6(5) . . . . ?
C56 C57 C58 C59 -61.7(5) . . . . ?
C57 C58 C59 C60 -61.7(5) . . . . ?
C57 C58 C59 C51 60.8(5) . . . . ?
N51 C51 C59 C58 -57.6(5) . . . . ?
C52 C51 C59 C58 70.5(5) . . . . ?
N51 C51 C59 C60 63.0(4) . . . . ?
C52 C51 C59 C60 -168.8(4) . . . . ?
C61 N52 C60 C59 177.4(3) . . . . ?
C65 N52 C60 C59 -57.1(5) . . . . ?
C58 C59 C60 N52 59.7(4) . . . . ?
C51 C59 C60 N52 -62.7(5) . . . . ?
C60 N52 C61 C62 -176.7(4) . . . . ?
C65 N52 C61 C62 58.0(5) . . . . ?
N52 C61 C62 C63 -59.6(5) . . . . ?
C61 C62 C63 C64 57.5(5) . . . . ?
C62 C63 C64 C65 -55.2(5) . . . . ?
C58 C57 C65 N52 -59.6(4) . . . . ?
C56 C57 C65 N52 62.7(4) . . . . ?
C58 C57 C65 C64 177.9(4) . . . . ?
C56 C57 C65 C64 -59.8(5) . . . . ?
C60 N52 C65 C57 55.9(5) . . . . ?
C61 N52 C65 C57 -179.3(3) . . . . ?
C60 N52 C65 C64 -179.0(4) . . . . ?
C61 N52 C65 C64 -54.2(5) . . . . ?
C63 C64 C65 C57 175.6(4) . . . . ?
C63 C64 C65 N52 53.7(5) . . . . ?
C75 N71 C71 C72 54.8(5) . . . . ?
C76 N71 C71 C72 -70.6(5) . . . . ?
C75 N71 C71 C79 -178.2(4) . . . . ?
C76 N71 C71 C79 56.4(5) . . . . ?
N71 C71 C72 C73 -53.8(5) . . . . ?
C79 C71 C72 C73 -178.6(4) . . . . ?
C71 C72 C73 C74 52.2(5) . . . . ?
C72 C73 C74 C75 -53.1(6) . . . . ?
C76 N71 C75 C74 69.6(5) . . . . ?
C71 N71 C75 C74 -55.3(5) . . . . ?
C73 C74 C75 N71 55.5(6) . . . . ?
C75 N71 C76 C77 176.8(4) . . . . ?
C71 N71 C76 C77 -59.0(5) . . . . ?
N71 C76 C77 C78 60.8(5) . . . . ?
N71 C76 C77 C85 -62.0(5) . . . . ?
C76 C77 C78 C79 -60.4(5) . . . . ?
C85 C77 C78 C79 64.1(5) . . . . ?
C77 C78 C79 C80 -62.9(5) . . . . ?
C77 C78 C79 C71 60.3(5) . . . . ?
N71 C71 C79 C78 -57.8(5) . . . . ?
C72 C71 C79 C78 69.4(5) . . . . ?
N71 C71 C79 C80 63.5(4) . . . . ?
C72 C71 C79 C80 -169.4(4) . . . . ?
C81 N72 C80 C79 178.4(4) . . . . ?
C85 N72 C80 C79 -55.9(5) . . . . ?
C78 C79 C80 N72 59.6(5) . . . . ?
C71 C79 C80 N72 -63.5(5) . . . . ?
C80 N72 C81 C82 180.0(4) . . . . ?
C85 N72 C81 C82 54.9(5) . . . . ?
N72 C81 C82 C83 -55.0(5) . . . . ?
C81 C82 C83 C84 55.6(6) . . . . ?
C82 C83 C84 C85 -57.3(6) . . . . ?
C83 C84 C85 N72 56.5(5) . . . . ?
C83 C84 C85 C77 179.2(4) . . . . ?
C81 N72 C85 C84 -55.4(5) . . . . ?
C80 N72 C85 C84 -179.7(4) . . . . ?
C81 N72 C85 C77 178.6(4) . . . . ?
C80 N72 C85 C77 54.3(5) . . . . ?
C78 C77 C85 C84 177.7(4) . . . . ?
C76 C77 C85 C84 -60.2(5) . . . . ?
C78 C77 C85 N72 -59.2(5) . . . . ?
C76 C77 C85 N72 62.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H10 N12 0.90 2.61 3.416(6) 150.0 2_646 yes
N11 H11 O21 0.90 2.30 3.114(5) 150.3 . yes
N13 H17 N43 0.88 1.92 2.791(6) 169.1 . yes
N21 H20 N22 0.90 2.68 3.541(7) 160.1 2_756 yes
N21 H21 O11 0.90 2.41 3.176(5) 143.4 1_655 yes
N23 H27 N33 0.88 1.89 2.763(6) 171.2 . yes
N31 H31 O42 0.90 2.21 3.026(5) 150.8 . yes
N41 H41 O32 0.90 2.16 2.997(5) 154.6 1_455 yes
N52 H52 N51 1.00 1.94 2.652(6) 125.3 . yes
N72 H72 N71 1.00 1.99 2.683(6) 123.8 . yes

