# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1915951'
loop_
_audit_author_name
_audit_author_address
'Thomas Gelbrich'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Dapsone acetonitrile hemisolvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H12 N2 O2 S), C2 H3 N'
_chemical_formula_sum            'C26 H27 N5 O4 S2'
_chemical_formula_weight         537.64

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                   8.5132(2)
_cell_length_b                   16.1830(3)
_cell_length_c                   18.9865(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.818(2)
_cell_angle_gamma                90
_cell_volume                     2591.44(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11098
_cell_measurement_theta_min      3.2610
_cell_measurement_theta_max      29.5810

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_T_min  0.72772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
(CrysAlis PRO; Rigaku OD, 2017)
;

_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
;
Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'

_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_radiation_wavelength     0.71073

_diffrn_source                   'Rotating Anode'
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'

_diffrn_ambient_temperature      100(2)
_diffrn_reflns_number            23182
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.740
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_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             5290
_reflns_number_gt                4510
_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0480P)²+1.5077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5290
_refine_ls_number_parameters     386
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S1 S 0.31752(5) 0.63843(2) 0.38325(2) 0.01629(12) Uani 1 1 d . . . . .
O1 O 0.45398(14) 0.65754(7) 0.43443(7) 0.0211(3) Uani 1 1 d . . . . .
O2 O 0.27808(14) 0.69417(7) 0.32400(6) 0.0209(3) Uani 1 1 d . . . . .
N1 N 0.43746(19) 0.31865(10) 0.25012(9) 0.0236(3) Uani 1 1 d D . . . .
H1A H 0.5130(19) 0.2890(12) 0.2714(11) 0.036(6) Uiso 1 1 d D . . . .
H1B H 0.361(2) 0.2957(13) 0.2223(10) 0.037(6) Uiso 1 1 d D . . . .
N2 N -0.24747(19) 0.59943(10) 0.52924(9) 0.0240(3) Uani 1 1 d D . . . .
H2A H -0.3350(17) 0.6195(13) 0.5079(11) 0.034(6) Uiso 1 1 d D . . . .
H2B H -0.233(3) 0.5932(14) 0.5746(5) 0.033(6) Uiso 1 1 d D . . . .
C1 C 0.34982(19) 0.54098(10) 0.34723(9) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.2409(2) 0.51022(11) 0.29215(9) 0.0211(4) Uani 1 1 d . . . . .
H2 H 0.1481 0.5410 0.2757 0.030(6) Uiso 1 1 calc R . . . .
C3 C 0.2671(2) 0.43519(11) 0.26137(10) 0.0217(4) Uani 1 1 d . . . . .
H3 H 0.1914 0.4143 0.2242 0.025(5) Uiso 1 1 calc R . . . .
C4 C 0.4049(2) 0.38923(10) 0.28442(9) 0.0182(4) Uani 1 1 d . . . . .
C5 C 0.5107(2) 0.41995(11) 0.34145(9) 0.0185(4) Uani 1 1 d . . . . .
H5 H 0.6023 0.3888 0.3590 0.025(5) Uiso 1 1 calc R . . . .
C6 C 0.4838(2) 0.49481(10) 0.37236(9) 0.0173(3) Uani 1 1 d . . . . .
H6 H 0.5568 0.5149 0.4109 0.016(5) Uiso 1 1 calc R . . . .
C7 C 0.1508(2) 0.62957(10) 0.42725(9) 0.0162(3) Uani 1 1 d . . . . .
C8 C 0.1688(2) 0.60579(11) 0.49846(9) 0.0193(4) Uani 1 1 d . . . . .
H8 H 0.2716 0.5961 0.5235 0.021(5) Uiso 1 1 calc R . . . .
C9 C 0.0367(2) 0.59634(11) 0.53240(9) 0.0211(4) Uani 1 1 d . . . . .
H9 H 0.0491 0.5803 0.5810 0.023(5) Uiso 1 1 calc R . . . .
C10 C -0.1157(2) 0.61016(10) 0.49615(9) 0.0188(4) Uani 1 1 d . . . . .
C11 C -0.1317(2) 0.63384(10) 0.42443(10) 0.0194(4) Uani 1 1 d . . . . .
H11 H -0.2342 0.6432 0.3991 0.023(5) Uiso 1 1 calc R . . . .
C12 C 0.0005(2) 0.64358(10) 0.39042(9) 0.0180(4) Uani 1 1 d . . . . .
H12 H -0.0112 0.6598 0.3419 0.024(5) Uiso 1 1 calc R . . . .
S1' S 0.76842(5) 0.16896(3) 0.32157(2) 0.02079(13) Uani 1 1 d . . . . .
O1' O 0.76927(16) 0.18845(8) 0.24731(7) 0.0285(3) Uani 1 1 d . . . . .
O2' O 0.66864(15) 0.21880(8) 0.36089(7) 0.0277(3) Uani 1 1 d . . . . .
N1' N 0.5855(2) -0.18134(10) 0.34572(9) 0.0265(4) Uani 1 1 d D . . . .
H1A' H 0.596(3) -0.2149(11) 0.3115(9) 0.034(6) Uiso 1 1 d D . . . .
H1B' H 0.511(2) -0.1926(14) 0.3705(11) 0.035(6) Uiso 1 1 d D . . . .
N2' N 1.42630(19) 0.19791(10) 0.46227(9) 0.0276(4) Uani 1 1 d D . . . .
H2A' H 1.495(2) 0.2070(16) 0.4338(11) 0.047(7) Uiso 1 1 d D . . . .
H2B' H 1.442(3) 0.2198(14) 0.5040(7) 0.044(7) Uiso 1 1 d D . . . .
C1' C 0.7087(2) 0.06581(11) 0.32725(9) 0.0196(4) Uani 1 1 d . . . . .
C2' C 0.6429(2) 0.03898(11) 0.38671(10) 0.0209(4) Uani 1 1 d . . . . .
H2' H 0.6268 0.0770 0.4232 0.020(5) Uiso 1 1 calc R . . . .
C3' C 0.6012(2) -0.04301(11) 0.39235(10) 0.0218(4) Uani 1 1 d . . . . .
H3' H 0.5558 -0.0610 0.4327 0.020(5) Uiso 1 1 calc R . . . .
C4' C 0.6250(2) -0.10006(11) 0.33921(10) 0.0208(4) Uani 1 1 d . . . . .
C5' C 0.6927(2) -0.07183(11) 0.28010(10) 0.0238(4) Uani 1 1 d . . . . .
H5' H 0.7104 -0.1097 0.2438 0.023(5) Uiso 1 1 calc R . . . .
C6' C 0.7339(2) 0.01009(11) 0.27399(10) 0.0231(4) Uani 1 1 d . . . . .
H6' H 0.7793 0.0284 0.2337 0.027(5) Uiso 1 1 calc R . . . .
C7' C 0.9619(2) 0.17613(10) 0.36410(9) 0.0182(4) Uani 1 1 d . . . . .
C8' C 1.0872(2) 0.16908(11) 0.32404(10) 0.0208(4) Uani 1 1 d . . . . .
H8' H 1.0662 0.1596 0.2743 0.022(5) Uiso 1 1 calc R . . . .
C9' C 1.2410(2) 0.17592(11) 0.35671(10) 0.0222(4) Uani 1 1 d . . . . .
H9' H 1.3259 0.1714 0.3292 0.031(6) Uiso 1 1 calc R . . . .
C10' C 1.2737(2) 0.18948(10) 0.43031(10) 0.0201(4) Uani 1 1 d . . . . .
C11' C 1.1463(2) 0.19290(11) 0.47020(9) 0.0208(4) Uani 1 1 d . . . . .
H11' H 1.1668 0.1990 0.5204 0.027(5) Uiso 1 1 calc R . . . .
C12' C 0.9925(2) 0.18753(10) 0.43751(9) 0.0196(4) Uani 1 1 d . . . . .
H12' H 0.9072 0.1916 0.4648 0.026(5) Uiso 1 1 calc R . . . .
N1S N 0.7231(2) 0.14907(10) 0.57193(9) 0.0288(4) Uani 1 1 d . . . . .
C1S C 0.8176(2) 0.09967(11) 0.58198(9) 0.0225(4) Uani 1 1 d . . . . .
C2S C 0.9391(3) 0.03582(14) 0.59526(12) 0.0369(5) Uani 1 1 d . . . . .
H2S1 H 0.8968 -0.0167 0.5752 0.099(12) Uiso 1 1 calc R . . . .
H2S2 H 0.9702 0.0297 0.6466 0.096(12) Uiso 1 1 calc R . . . .
H2S3 H 1.0318 0.0516 0.5729 0.069(9) Uiso 1 1 calc R . . . .


_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
S1 O1 1.4430(13) . ?
S1 O2 1.4454(12) . ?
S1 C7 1.7480(16) . ?
S1 C1 1.7553(16) . ?
N1 C4 1.362(2) . ?
N1 H1A 0.858(10) . ?
N1 H1B 0.862(10) . ?
N2 C10 1.369(2) . ?
N2 H2A 0.862(10) . ?
N2 H2B 0.858(9) . ?
C1 C2 1.392(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.408(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(2) . ?
C5 C6 1.379(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.391(2) . ?
C7 C8 1.394(2) . ?
C8 C9 1.379(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(2) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
S1' O1' 1.4457(14) . ?
S1' O2' 1.4499(13) . ?
S1' C7' 1.7372(18) . ?
S1' C1' 1.7525(17) . ?
N1' C4' 1.367(2) . ?
N1' H1A' 0.861(10) . ?
N1' H1B' 0.858(10) . ?
N2' C10' 1.364(2) . ?
N2' H2A' 0.863(10) . ?
N2' H2B' 0.861(10) . ?
C1' C6' 1.393(2) . ?
C1' C2' 1.396(2) . ?
C2' C3' 1.381(2) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.403(2) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.406(2) . ?
C5' C6' 1.380(3) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C7' C12' 1.395(2) . ?
C7' C8' 1.396(2) . ?
C8' C9' 1.375(3) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.404(2) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.406(2) . ?
C11' C12' 1.373(3) . ?
C11' H11' 0.9500 . ?
C12' H12' 0.9500 . ?
N1S C1S 1.132(2) . ?
C1S C2S 1.459(3) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 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
O1 S1 O2 118.09(7) . . ?
O1 S1 C7 109.10(8) . . ?
O2 S1 C7 107.78(8) . . ?
O1 S1 C1 107.48(8) . . ?
O2 S1 C1 106.83(7) . . ?
C7 S1 C1 107.03(8) . . ?
C4 N1 H1A 115.6(16) . . ?
C4 N1 H1B 117.9(15) . . ?
H1A N1 H1B 120(2) . . ?
C10 N2 H2A 116.5(15) . . ?
C10 N2 H2B 117.6(15) . . ?
H2A N2 H2B 121(2) . . ?
C2 C1 C6 119.77(16) . . ?
C2 C1 S1 119.36(13) . . ?
C6 C1 S1 120.86(13) . . ?
C3 C2 C1 120.25(16) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.63(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N1 C4 C5 121.03(16) . . ?
N1 C4 C3 120.64(16) . . ?
C5 C4 C3 118.27(16) . . ?
C6 C5 C4 120.91(16) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 120.09(16) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C12 C7 C8 120.32(15) . . ?
C12 C7 S1 119.83(13) . . ?
C8 C7 S1 119.81(13) . . ?
C9 C8 C7 119.67(16) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.83(16) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
N2 C10 C9 121.05(16) . . ?
N2 C10 C11 120.18(16) . . ?
C9 C10 C11 118.75(15) . . ?
C12 C11 C10 120.51(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 119.92(16) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
O1' S1' O2' 117.50(8) . . ?
O1' S1' C7' 107.97(8) . . ?
O2' S1' C7' 107.97(8) . . ?
O1' S1' C1' 107.93(8) . . ?
O2' S1' C1' 107.63(8) . . ?
C7' S1' C1' 107.44(8) . . ?
C4' N1' H1A' 119.0(15) . . ?
C4' N1' H1B' 117.6(16) . . ?
H1A' N1' H1B' 116(2) . . ?
C10' N2' H2A' 115.2(18) . . ?
C10' N2' H2B' 118.2(16) . . ?
H2A' N2' H2B' 118(2) . . ?
C6' C1' C2' 120.28(16) . . ?
C6' C1' S1' 119.80(13) . . ?
C2' C1' S1' 119.85(13) . . ?
C3' C2' C1' 119.81(16) . . ?
C3' C2' H2' 120.1 . . ?
C1' C2' H2' 120.1 . . ?
C2' C3' C4' 120.84(16) . . ?
C2' C3' H3' 119.6 . . ?
C4' C3' H3' 119.6 . . ?
N1' C4' C3' 120.44(16) . . ?
N1' C4' C5' 121.16(16) . . ?
C3' C4' C5' 118.39(16) . . ?
C6' C5' C4' 121.05(17) . . ?
C6' C5' H5' 119.5 . . ?
C4' C5' H5' 119.5 . . ?
C5' C6' C1' 119.64(16) . . ?
C5' C6' H6' 120.2 . . ?
C1' C6' H6' 120.2 . . ?
C12' C7' C8' 120.17(16) . . ?
C12' C7' S1' 120.63(13) . . ?
C8' C7' S1' 119.19(14) . . ?
C9' C8' C7' 119.91(17) . . ?
C9' C8' H8' 120.0 . . ?
C7' C8' H8' 120.0 . . ?
C8' C9' C10' 120.63(16) . . ?
C8' C9' H9' 119.7 . . ?
C10' C9' H9' 119.7 . . ?
N2' C10' C9' 120.44(16) . . ?
N2' C10' C11' 120.96(17) . . ?
C9' C10' C11' 118.59(16) . . ?
C12' C11' C10' 120.81(16) . . ?
C12' C11' H11' 119.6 . . ?
C10' C11' H11' 119.6 . . ?
C11' C12' C7' 119.79(16) . . ?
C11' C12' H12' 120.1 . . ?
C7' C12' H12' 120.1 . . ?
N1S C1S C2S 179.7(2) . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?

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
N1 H1A O2' 0.858(10) 2.307(12) 3.127(2) 160(2) .
N2 H2A O1 0.862(10) 2.207(11) 3.056(2) 168(2) 1_455
N1' H1A' O1' 0.861(10) 2.314(13) 3.112(2) 154(2) 2_645
N1' H1B' N1S 0.858(10) 2.502(14) 3.276(2) 151(2) 3_656
N1 H1B O2 0.862(10) 2.144(13) 2.950(2) 155(2) 2_545
N2' H2A' O2' 0.863(10) 2.165(10) 3.026(2) 175(2) 1_655
N2' H2B' O1 0.861(10) 2.410(17) 3.133(2) 142(2) 3_766

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.057

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1915952'
loop_
_audit_author_name
_audit_author_address
'Thomas Gelbrich'
;University of Innsbruck
Austria
;
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Dapsone nitromethane hemisolvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H12 N2 O2 S), C H3 N O2'
_chemical_formula_sum            'C25 H27 N5 O6 S2'
_chemical_formula_weight         557.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   8.4167(2)
_cell_length_b                   16.3415(3)
_cell_length_c                   19.1383(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.832(2)
_cell_angle_gamma                90
_cell_volume                     2618.69(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29663
_cell_measurement_theta_min      2.2980
_cell_measurement_theta_max      70.1370

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.275
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_T_min  0.51469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
(CrysAlis PRO; Rigaku OD, 2017)
;

_diffrn_ambient_temperature      100(2)

_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'HyPix 6000HE detector'
_diffrn_detector_area_resol_mean 22.2222

_diffrn_measurement_device       'four-circle quarter χ goniometer'
_diffrn_measurement_device_type  
;
Rigaku 007HF equipped with Varimax confocal mirrors and an
AFC11 goniometer and HyPix 6000 detector
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating Anode'
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_source_current           30.0
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007HF'
_diffrn_reflns_number            48993
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.564
_diffrn_reflns_theta_max         70.769
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4977
_reflns_number_gt                4880
_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.
;

_computing_data_collection       
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_cell_refinement       
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_reduction        
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0506P)²+2.8727P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4977
_refine_ls_number_parameters     395
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S1 S 0.32081(6) 0.64543(3) 0.38262(3) 0.02619(15) Uani 1 1 d . . . . .
O1 O 0.45515(19) 0.66404(10) 0.43330(9) 0.0325(4) Uani 1 1 d . . . . .
O2 O 0.2842(2) 0.70229(10) 0.32543(9) 0.0325(4) Uani 1 1 d . . . . .
N1 N 0.4330(3) 0.32500(12) 0.25300(11) 0.0341(5) Uani 1 1 d D . . . .
H1A H 0.359(3) 0.304(2) 0.2237(14) 0.057(10) Uiso 1 1 d D . . . .
H1B H 0.507(3) 0.2963(18) 0.2755(15) 0.056(10) Uiso 1 1 d D . . . .
N2 N -0.2574(3) 0.59737(13) 0.52791(12) 0.0361(5) Uani 1 1 d D . . . .
H2A H -0.239(3) 0.5915(17) 0.5727(6) 0.031(7) Uiso 1 1 d D . . . .
H2B H -0.346(2) 0.6179(16) 0.5082(13) 0.035(7) Uiso 1 1 d D . . . .
C1 C 0.3562(3) 0.54976(13) 0.34547(11) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.2527(3) 0.52239(15) 0.28872(12) 0.0314(5) Uani 1 1 d . . . . .
H2 H 0.1657 0.5557 0.2704 0.042(8) Uiso 1 1 calc R . . . .
C3 C 0.2764(3) 0.44710(15) 0.25917(13) 0.0323(5) Uani 1 1 d . . . . .
H3 H 0.2051 0.4288 0.2207 0.039(7) Uiso 1 1 calc R . . . .
C4 C 0.4044(3) 0.39695(13) 0.28510(11) 0.0272(5) Uani 1 1 d . . . . .
C5 C 0.5060(3) 0.42477(13) 0.34311(11) 0.0268(5) Uani 1 1 d . . . . .
H5 H 0.5921 0.3913 0.3620 0.033(7) Uiso 1 1 calc R . . . .
C6 C 0.4819(3) 0.50028(13) 0.37298(11) 0.0265(4) Uani 1 1 d . . . . .
H6 H 0.5512 0.5184 0.4122 0.031(7) Uiso 1 1 calc R . . . .
C7 C 0.1507(3) 0.63423(13) 0.42676(11) 0.0257(4) Uani 1 1 d . . . . .
C8 C 0.1643(3) 0.60728(14) 0.49608(12) 0.0297(5) Uani 1 1 d . . . . .
H8 H 0.2668 0.5968 0.5200 0.039(7) Uiso 1 1 calc R . . . .
C9 C 0.0294(3) 0.59576(14) 0.53003(12) 0.0309(5) Uani 1 1 d . . . . .
H9 H 0.0393 0.5778 0.5775 0.039(7) Uiso 1 1 calc R . . . .
C10 C -0.1228(3) 0.61029(13) 0.49502(12) 0.0291(5) Uani 1 1 d . . . . .
C11 C -0.1352(3) 0.63672(14) 0.42502(12) 0.0291(5) Uani 1 1 d . . . . .
H11 H -0.2375 0.6466 0.4007 0.029(6) Uiso 1 1 calc R . . . .
C12 C 0.0006(3) 0.64861(13) 0.39096(12) 0.0279(5) Uani 1 1 d . . . . .
H12 H -0.0085 0.6665 0.3435 0.029(7) Uiso 1 1 calc R . . . .
S1' S 0.74628(7) 0.17307(3) 0.32123(3) 0.03398(17) Uani 1 1 d . . . . .
O1' O 0.7571(2) 0.19664(11) 0.24913(10) 0.0434(5) Uani 1 1 d . . . . .
O2' O 0.6390(2) 0.21979(10) 0.36057(11) 0.0431(5) Uani 1 1 d . . . . .
N1' N 0.5798(3) -0.17676(13) 0.33631(13) 0.0411(5) Uani 1 1 d D . . . .
H1A' H 0.505(3) -0.1877(19) 0.3620(14) 0.044(9) Uiso 1 1 d D . . . .
H1B' H 0.606(4) -0.2090(17) 0.3039(13) 0.057(10) Uiso 1 1 d D . . . .
N2' N 1.3924(3) 0.19646(15) 0.47133(15) 0.0470(6) Uani 1 1 d D . . . .
H2A' H 1.393(4) 0.2126(19) 0.5144(8) 0.046(9) Uiso 1 1 d D . . . .
H2B' H 1.466(3) 0.211(2) 0.4458(16) 0.059(11) Uiso 1 1 d D . . . .
C1' C 0.6860(3) 0.07096(14) 0.32222(12) 0.0306(5) Uani 1 1 d . . . . .
C2' C 0.6051(3) 0.04185(14) 0.37720(13) 0.0327(5) Uani 1 1 d . . . . .
H2' H 0.5752 0.0787 0.4120 0.050(9) Uiso 1 1 calc R . . . .
C3' C 0.5682(3) -0.04016(14) 0.38139(13) 0.0327(5) Uani 1 1 d . . . . .
H3' H 0.5133 -0.0595 0.4191 0.042(8) Uiso 1 1 calc R . . . .
C4' C 0.6114(3) -0.09522(15) 0.33022(13) 0.0318(5) Uani 1 1 d . . . . .
C5' C 0.6902(3) -0.06491(15) 0.27430(13) 0.0348(5) Uani 1 1 d . . . . .
H5' H 0.7179 -0.1013 0.2388 0.053(9) Uiso 1 1 calc R . . . .
C6' C 0.7277(3) 0.01717(15) 0.27044(13) 0.0345(5) Uani 1 1 d . . . . .
H6' H 0.7818 0.0370 0.2326 0.046(8) Uiso 1 1 calc R . . . .
C7' C 0.9365(3) 0.17912(13) 0.36603(12) 0.0300(5) Uani 1 1 d . . . . .
C8' C 1.0701(3) 0.17638(15) 0.32835(13) 0.0332(5) Uani 1 1 d . . . . .
H8' H 1.0572 0.1706 0.2787 0.056(10) Uiso 1 1 calc R . . . .
C9' C 1.2208(3) 0.18216(15) 0.36361(13) 0.0352(5) Uani 1 1 d . . . . .
H9' H 1.3115 0.1808 0.3379 0.050(9) Uiso 1 1 calc R . . . .
C10' C 1.2420(3) 0.19005(14) 0.43677(13) 0.0347(5) Uani 1 1 d . . . . .
C11' C 1.1066(3) 0.19028(15) 0.47386(13) 0.0378(6) Uani 1 1 d . . . . .
H11' H 1.1195 0.1936 0.5237 0.037(7) Uiso 1 1 calc R . . . .
C12' C 0.9551(3) 0.18574(14) 0.43919(13) 0.0340(5) Uani 1 1 d . . . . .
H12' H 0.8642 0.1871 0.4648 0.039(8) Uiso 1 1 calc R . . . .
O1S O 0.7712(2) 0.13592(11) 0.58651(10) 0.0442(5) Uani 1 1 d . . . . .
N1S N 0.8263(3) 0.06988(13) 0.57026(11) 0.0362(5) Uani 1 1 d . . . . .
O2S O 0.7594(3) 0.02423(15) 0.52639(11) 0.0578(6) Uani 1 1 d . . . . .
C1S C 0.9808(3) 0.0432(2) 0.60508(16) 0.0483(7) Uani 1 1 d . . . . .
H1S1 H 0.9688 -0.0105 0.6267 0.086(13) Uiso 1 1 calc R . . . .
H1S2 H 1.0184 0.0829 0.6414 0.096(14) Uiso 1 1 calc R . . . .
H1S3 H 1.0585 0.0394 0.5704 0.092(14) Uiso 1 1 calc R . . . .


_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
S1 O2 1.4448(17) . ?
S1 O1 1.4453(16) . ?
S1 C7 1.745(2) . ?
S1 C1 1.755(2) . ?
N1 C4 1.359(3) . ?
N1 H1A 0.862(10) . ?
N1 H1B 0.861(10) . ?
N2 C10 1.367(3) . ?
N2 H2A 0.862(10) . ?
N2 H2B 0.865(10) . ?
C1 C6 1.392(3) . ?
C1 C2 1.395(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(3) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.391(3) . ?
C7 C12 1.395(3) . ?
C8 C9 1.378(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
S1' O1' 1.4443(19) . ?
S1' O2' 1.4503(19) . ?
S1' C7' 1.740(2) . ?
S1' C1' 1.745(2) . ?
N1' C4' 1.366(3) . ?
N1' H1A' 0.858(10) . ?
N1' H1B' 0.858(10) . ?
N2' C10' 1.371(3) . ?
N2' H2A' 0.865(10) . ?
N2' H2B' 0.859(10) . ?
C1' C2' 1.394(3) . ?
C1' C6' 1.396(3) . ?
C2' C3' 1.380(3) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.405(3) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.405(3) . ?
C5' C6' 1.382(3) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C7' C8' 1.397(3) . ?
C7' C12' 1.397(3) . ?
C8' C9' 1.378(3) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.399(4) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.402(4) . ?
C11' C12' 1.379(4) . ?
C11' H11' 0.9500 . ?
C12' H12' 0.9500 . ?
O1S N1S 1.227(3) . ?
N1S O2S 1.217(3) . ?
N1S C1S 1.466(3) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 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
O2 S1 O1 117.74(10) . . ?
O2 S1 C7 108.17(10) . . ?
O1 S1 C7 108.76(10) . . ?
O2 S1 C1 107.33(10) . . ?
O1 S1 C1 107.82(10) . . ?
C7 S1 C1 106.49(10) . . ?
C4 N1 H1A 119(2) . . ?
C4 N1 H1B 113(2) . . ?
H1A N1 H1B 123(3) . . ?
C10 N2 H2A 113.7(18) . . ?
C10 N2 H2B 117.0(19) . . ?
H2A N2 H2B 122(3) . . ?
C6 C1 C2 119.9(2) . . ?
C6 C1 S1 121.18(17) . . ?
C2 C1 S1 118.87(17) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
N1 C4 C3 120.6(2) . . ?
N1 C4 C5 121.0(2) . . ?
C3 C4 C5 118.3(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 C7 C12 120.3(2) . . ?
C8 C7 S1 120.18(17) . . ?
C12 C7 S1 119.43(17) . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N2 C10 C11 120.2(2) . . ?
N2 C10 C9 120.8(2) . . ?
C11 C10 C9 119.0(2) . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
O1' S1' O2' 117.29(12) . . ?
O1' S1' C7' 108.14(12) . . ?
O2' S1' C7' 107.72(11) . . ?
O1' S1' C1' 108.19(11) . . ?
O2' S1' C1' 107.50(11) . . ?
C7' S1' C1' 107.64(11) . . ?
C4' N1' H1A' 114(2) . . ?
C4' N1' H1B' 118(2) . . ?
H1A' N1' H1B' 123(3) . . ?
C10' N2' H2A' 113(2) . . ?
C10' N2' H2B' 115(2) . . ?
H2A' N2' H2B' 122(3) . . ?
C2' C1' C6' 119.9(2) . . ?
C2' C1' S1' 119.97(18) . . ?
C6' C1' S1' 119.99(19) . . ?
C3' C2' C1' 120.4(2) . . ?
C3' C2' H2' 119.8 . . ?
C1' C2' H2' 119.8 . . ?
C2' C3' C4' 120.4(2) . . ?
C2' C3' H3' 119.8 . . ?
C4' C3' H3' 119.8 . . ?
N1' C4' C3' 119.9(2) . . ?
N1' C4' C5' 121.3(2) . . ?
C3' C4' C5' 118.7(2) . . ?
C6' C5' C4' 120.7(2) . . ?
C6' C5' H5' 119.6 . . ?
C4' C5' H5' 119.6 . . ?
C5' C6' C1' 119.8(2) . . ?
C5' C6' H6' 120.1 . . ?
C1' C6' H6' 120.1 . . ?
C8' C7' C12' 120.4(2) . . ?
C8' C7' S1' 119.50(18) . . ?
C12' C7' S1' 120.1(2) . . ?
C9' C8' C7' 119.6(2) . . ?
C9' C8' H8' 120.2 . . ?
C7' C8' H8' 120.2 . . ?
C8' C9' C10' 120.9(2) . . ?
C8' C9' H9' 119.5 . . ?
C10' C9' H9' 119.5 . . ?
N2' C10' C9' 120.5(3) . . ?
N2' C10' C11' 120.9(2) . . ?
C9' C10' C11' 118.6(2) . . ?
C12' C11' C10' 121.1(2) . . ?
C12' C11' H11' 119.5 . . ?
C10' C11' H11' 119.5 . . ?
C11' C12' C7' 119.4(2) . . ?
C11' C12' H12' 120.3 . . ?
C7' C12' H12' 120.3 . . ?
O2S N1S O1S 123.6(2) . . ?
O2S N1S C1S 117.3(2) . . ?
O1S N1S C1S 119.1(2) . . ?
N1S C1S H1S1 109.5 . . ?
N1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
N1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?

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
N1 H1A O2 0.862(10) 2.212(18) 3.009(3) 154(3) 2_545
N1 H1B O2' 0.861(10) 2.253(15) 3.078(3) 160(3) .
N2 H2B O1 0.865(10) 2.225(12) 3.071(3) 166(3) 1_455
N1' H1A' O2 0.858(10) 2.63(3) 3.168(3) 122(2) 1_545
N1' H1B' O1' 0.858(10) 2.232(16) 3.049(3) 159(3) 2_645
N2' H2A' O1 0.865(10) 2.54(3) 3.114(3) 125(3) 3_766
N2' H2B' O2' 0.859(10) 2.299(14) 3.137(4) 165(3) 1_655

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: nitromethane'
