# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_FA
_database_code_depnum_ccdc_archive 'CCDC 1589279'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N2 O2 S'
_chemical_formula_sum            'C11 H12 N2 O2 S'
_chemical_formula_weight         236.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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                   5.224(3)
_cell_length_b                   6.014(4)
_cell_length_c                   36.61(2)
_cell_angle_alpha                87.300(14)
_cell_angle_beta                 87.390(13)
_cell_angle_gamma                81.545(14)
_cell_volume                     1135.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5229
_cell_measurement_theta_max      26.489
_cell_measurement_theta_min      2.229

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             496.15
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5484
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4307
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.787
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4307
_reflns_number_gt                3280
_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.
;

_computing_data_collection       ?
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0360P)²+1.8158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4307
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.38120(19) 0.94983(17) 0.37242(3) 0.0257(3) Uani 1 1 d . . . . .
O1 O 0.4763(5) 0.6097(5) 0.45676(7) 0.0251(6) Uani 1 1 d . . . . .
H1 H 0.3304 0.6791 0.4543 0.038 Uiso 1 1 d R U . . .
O2 O 1.0180(5) 0.8898(5) 0.45625(7) 0.0250(6) Uani 1 1 d . . . . .
N1 N 0.6625(5) 0.7413(5) 0.44165(8) 0.0196(7) Uani 1 1 d . . . . .
N2 N 0.7508(6) 0.7860(6) 0.50232(9) 0.0261(8) Uani 1 1 d . . . . .
H2A H 0.8430 0.8304 0.5187 0.031 Uiso 1 1 d R U . . .
H2B H 0.6141 0.7276 0.5088 0.031 Uiso 1 1 d R U . . .
C8 C 0.5762(7) 0.6883(6) 0.37812(10) 0.0197(8) Uani 1 1 d . . . . .
C9 C 0.7789(7) 0.6586(7) 0.40648(10) 0.0232(9) Uani 1 1 d . . . . .
H9 H 0.9099 0.7535 0.3985 0.028 Uiso 1 1 calc R U . . .
C11 C 0.8205(7) 0.8065(6) 0.46705(10) 0.0194(8) Uani 1 1 d . . . . .
C10 C 0.9165(8) 0.4157(7) 0.41003(12) 0.0334(11) Uani 1 1 d . . . . .
H10A H 1.0498 0.4064 0.4275 0.050 Uiso 1 1 calc R U . . .
H10B H 0.9925 0.3703 0.3867 0.050 Uiso 1 1 calc R U . . .
H10C H 0.7935 0.3182 0.4181 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5258(7) 0.5381(7) 0.35349(10) 0.0242(9) Uani 1 1 d . . . . .
H7 H 0.6133 0.3922 0.3523 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3208(7) 0.6313(7) 0.32932(11) 0.0249(9) Uani 1 1 d . . . . .
C1 C 0.2231(7) 0.8548(7) 0.33667(11) 0.0263(9) Uani 1 1 d . . . . .
C2 C 0.0156(8) 0.9746(8) 0.31731(11) 0.0311(10) Uani 1 1 d . . . . .
H2 H -0.0481 1.1231 0.3224 0.037 Uiso 1 1 calc R U . . .
C3 C -0.0902(8) 0.8656(9) 0.29069(12) 0.0378(12) Uani 1 1 d . . . . .
H3 H -0.2288 0.9410 0.2779 0.045 Uiso 1 1 calc R U . . .
C4 C 0.0080(9) 0.6432(9) 0.28268(12) 0.0388(12) Uani 1 1 d . . . . .
H4 H -0.0651 0.5734 0.2644 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2133(8) 0.5252(8) 0.30165(11) 0.0334(10) Uani 1 1 d . . . . .
H5 H 0.2784 0.3778 0.2961 0.040 Uiso 1 1 calc R U . . .
S2 S 0.18609(19) 0.65345(18) 0.86904(3) 0.0258(3) Uani 1 1 d . . . . .
O3 O 0.0456(5) 0.9139(5) 0.95646(7) 0.0242(6) Uani 1 1 d . . . . .
H3A H 0.1938 0.8493 0.9531 0.036 Uiso 1 1 d R U . . .
O4 O -0.4957(5) 0.6325(4) 0.95564(7) 0.0238(6) Uani 1 1 d . . . . .
N3 N -0.1325(5) 0.7903(5) 0.94094(8) 0.0194(7) Uani 1 1 d . . . . .
N4 N -0.2489(6) 0.7091(6) 1.00163(9) 0.0256(8) Uani 1 1 d . . . . .
H4A H -0.3455 0.6518 1.0180 0.031 Uiso 1 1 d R U . . .
H4B H -0.1164 0.7659 1.0079 0.031 Uiso 1 1 d R U . . .
C19 C -0.0235(7) 0.9024(6) 0.87788(10) 0.0195(8) Uani 1 1 d . . . . .
C20 C -0.2382(7) 0.9002(6) 0.90677(10) 0.0215(9) Uani 1 1 d . . . . .
H20 H -0.3607 0.8077 0.8981 0.026 Uiso 1 1 calc R U . . .
C22 C -0.3043(7) 0.7109(6) 0.96651(10) 0.0182(8) Uani 1 1 d . . . . .
C21 C -0.3866(8) 1.1351(7) 0.91241(12) 0.0338(11) Uani 1 1 d . . . . .
H21A H -0.5263 1.1258 0.9301 0.051 Uiso 1 1 calc R U . . .
H21B H -0.4550 1.1970 0.8896 0.051 Uiso 1 1 calc R U . . .
H21C H -0.2718 1.2302 0.9210 0.051 Uiso 1 1 calc R U . . .
C18 C 0.0275(7) 1.0756(7) 0.85521(10) 0.0232(9) Uani 1 1 d . . . . .
H18 H -0.0668 1.2192 0.8560 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2426(7) 1.0161(7) 0.82970(11) 0.0259(9) Uani 1 1 d . . . . .
C12 C 0.3497(7) 0.7888(7) 0.83431(11) 0.0249(9) Uani 1 1 d . . . . .
C13 C 0.5671(8) 0.6979(8) 0.81292(12) 0.0339(11) Uani 1 1 d . . . . .
H13 H 0.6384 0.5475 0.8159 0.041 Uiso 1 1 calc R U . . .
C14 C 0.6721(8) 0.8391(9) 0.78725(12) 0.0398(12) Uani 1 1 d . . . . .
H14 H 0.8162 0.7820 0.7729 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5668(9) 1.0643(9) 0.78240(12) 0.0418(13) Uani 1 1 d . . . . .
H15 H 0.6408 1.1551 0.7649 0.050 Uiso 1 1 calc R U . . .
C16 C 0.3541(8) 1.1541(8) 0.80330(12) 0.0348(11) Uani 1 1 d . . . . .
H16 H 0.2847 1.3048 0.8000 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
S1 C1 1.741(4) . ?
S1 C8 1.753(4) . ?
O1 N1 1.420(4) . ?
O1 H1 0.8202 . ?
O2 C11 1.252(4) . ?
N1 C11 1.378(5) . ?
N1 C9 1.475(5) . ?
N2 C11 1.331(5) . ?
N2 H2A 0.8612 . ?
N2 H2B 0.8602 . ?
C8 C7 1.366(5) . ?
C8 C9 1.503(5) . ?
C9 C10 1.533(5) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 C6 1.451(5) . ?
C7 H7 0.9300 . ?
C6 C1 1.400(6) . ?
C6 C5 1.402(6) . ?
C1 C2 1.410(6) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
S2 C12 1.737(4) . ?
S2 C19 1.754(4) . ?
O3 N3 1.426(4) . ?
O3 H3A 0.8201 . ?
O4 C22 1.254(4) . ?
N3 C22 1.385(5) . ?
N3 C20 1.478(5) . ?
N4 C22 1.330(5) . ?
N4 H4A 0.8590 . ?
N4 H4B 0.8605 . ?
C19 C18 1.351(5) . ?
C19 C20 1.507(5) . ?
C20 C21 1.526(5) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 C17 1.443(5) . ?
C18 H18 0.9300 . ?
C17 C12 1.404(6) . ?
C17 C16 1.406(6) . ?
C12 C13 1.407(6) . ?
C13 C14 1.385(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
C1 S1 C8 91.65(19) . . ?
N1 O1 H1 109.5 . . ?
C11 N1 O1 114.0(3) . . ?
C11 N1 C9 119.0(3) . . ?
O1 N1 C9 112.5(3) . . ?
C11 N2 H2A 120.0 . . ?
C11 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C7 C8 C9 128.6(3) . . ?
C7 C8 S1 112.2(3) . . ?
C9 C8 S1 119.2(3) . . ?
N1 C9 C8 109.6(3) . . ?
N1 C9 C10 112.4(3) . . ?
C8 C9 C10 112.4(3) . . ?
N1 C9 H9 107.4 . . ?
C8 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
O2 C11 N2 122.4(4) . . ?
O2 C11 N1 119.3(3) . . ?
N2 C11 N1 118.2(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C7 C6 112.6(4) . . ?
C8 C7 H7 123.7 . . ?
C6 C7 H7 123.7 . . ?
C1 C6 C5 119.3(4) . . ?
C1 C6 C7 112.2(4) . . ?
C5 C6 C7 128.5(4) . . ?
C6 C1 C2 121.5(4) . . ?
C6 C1 S1 111.4(3) . . ?
C2 C1 S1 127.1(3) . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C12 S2 C19 91.37(19) . . ?
N3 O3 H3A 109.7 . . ?
C22 N3 O3 113.4(3) . . ?
C22 N3 C20 117.8(3) . . ?
O3 N3 C20 112.2(3) . . ?
C22 N4 H4A 120.1 . . ?
C22 N4 H4B 119.9 . . ?
H4A N4 H4B 120.0 . . ?
C18 C19 C20 128.0(3) . . ?
C18 C19 S2 112.1(3) . . ?
C20 C19 S2 119.7(3) . . ?
N3 C20 C19 109.7(3) . . ?
N3 C20 C21 112.8(3) . . ?
C19 C20 C21 112.0(3) . . ?
N3 C20 H20 107.4 . . ?
C19 C20 H20 107.4 . . ?
C21 C20 H20 107.4 . . ?
O4 C22 N4 122.9(3) . . ?
O4 C22 N3 119.1(3) . . ?
N4 C22 N3 117.8(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C18 C17 113.4(4) . . ?
C19 C18 H18 123.3 . . ?
C17 C18 H18 123.3 . . ?
C12 C17 C16 119.5(4) . . ?
C12 C17 C18 111.7(4) . . ?
C16 C17 C18 128.8(4) . . ?
C17 C12 C13 120.8(4) . . ?
C17 C12 S2 111.4(3) . . ?
C13 C12 S2 127.7(4) . . ?
C14 C13 C12 118.1(4) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 C15 121.5(4) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.5(5) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?

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
C1 S1 C8 C7 1.1(3) . . . . ?
C1 S1 C8 C9 178.0(3) . . . . ?
C11 N1 C9 C8 -156.7(3) . . . . ?
O1 N1 C9 C8 66.2(4) . . . . ?
C11 N1 C9 C10 77.5(4) . . . . ?
O1 N1 C9 C10 -59.6(4) . . . . ?
C7 C8 C9 N1 -134.1(4) . . . . ?
S1 C8 C9 N1 49.6(4) . . . . ?
C7 C8 C9 C10 -8.4(6) . . . . ?
S1 C8 C9 C10 175.3(3) . . . . ?
O1 N1 C11 O2 168.1(3) . . . . ?
C9 N1 C11 O2 31.5(5) . . . . ?
O1 N1 C11 N2 -14.5(5) . . . . ?
C9 N1 C11 N2 -151.0(3) . . . . ?
C9 C8 C7 C6 -177.6(4) . . . . ?
S1 C8 C7 C6 -1.1(4) . . . . ?
C8 C7 C6 C1 0.5(5) . . . . ?
C8 C7 C6 C5 -178.0(4) . . . . ?
C5 C6 C1 C2 1.2(6) . . . . ?
C7 C6 C1 C2 -177.4(4) . . . . ?
C5 C6 C1 S1 179.0(3) . . . . ?
C7 C6 C1 S1 0.4(4) . . . . ?
C8 S1 C1 C6 -0.8(3) . . . . ?
C8 S1 C1 C2 176.8(4) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
S1 C1 C2 C3 -177.4(3) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C1 C6 C5 C4 -1.4(6) . . . . ?
C7 C6 C5 C4 177.0(4) . . . . ?
C12 S2 C19 C18 0.9(3) . . . . ?
C12 S2 C19 C20 177.9(3) . . . . ?
C22 N3 C20 C19 -160.7(3) . . . . ?
O3 N3 C20 C19 64.8(4) . . . . ?
C22 N3 C20 C21 73.8(4) . . . . ?
O3 N3 C20 C21 -60.7(4) . . . . ?
C18 C19 C20 N3 -133.8(4) . . . . ?
S2 C19 C20 N3 49.7(4) . . . . ?
C18 C19 C20 C21 -7.7(5) . . . . ?
S2 C19 C20 C21 175.8(3) . . . . ?
O3 N3 C22 O4 168.4(3) . . . . ?
C20 N3 C22 O4 34.4(5) . . . . ?
O3 N3 C22 N4 -15.7(5) . . . . ?
C20 N3 C22 N4 -149.6(3) . . . . ?
C20 C19 C18 C17 -177.5(4) . . . . ?
S2 C19 C18 C17 -0.8(4) . . . . ?
C19 C18 C17 C12 0.2(5) . . . . ?
C19 C18 C17 C16 -177.6(4) . . . . ?
C16 C17 C12 C13 0.1(6) . . . . ?
C18 C17 C12 C13 -177.9(4) . . . . ?
C16 C17 C12 S2 178.5(3) . . . . ?
C18 C17 C12 S2 0.5(4) . . . . ?
C19 S2 C12 C17 -0.8(3) . . . . ?
C19 S2 C12 C13 177.5(4) . . . . ?
C17 C12 C13 C14 0.0(6) . . . . ?
S2 C12 C13 C14 -178.1(3) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C16 0.3(7) . . . . ?
C14 C15 C16 C17 -0.1(7) . . . . ?
C12 C17 C16 C15 -0.1(6) . . . . ?
C18 C17 C16 C15 177.6(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
O1 H1 O2 0.82 1.91 2.718(4) 166.1 1_455
N2 H2A O2 0.86 2.18 2.950(4) 148.1 2_776
N2 H2B O1 0.86 2.43 3.106(4) 135.7 2_666
O3 H3A O4 0.82 1.93 2.723(4) 162.7 1_655
N4 H4A O4 0.86 2.17 2.960(4) 151.8 2_467
N4 H4B O3 0.86 2.46 3.132(4) 135.8 2_577

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1589280'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N2 O2 S, H2 O'
_chemical_formula_sum            'C11 H14 N2 O3 S'
_chemical_formula_weight         254.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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                   20.997(3)
_cell_length_b                   6.1061(9)
_cell_length_c                   9.6195(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.637(5)
_cell_angle_gamma                90
_cell_volume                     1227.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      2.925
_cell_measurement_theta_max      26.927

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.262
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5543
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.925
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5543
_reflns_number_gt                4667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.971
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.986

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 1857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5543
_refine_ls_number_parameters     356
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0990
_refine_ls_wR_factor_ref         0.2685
_refine_ls_wR_factor_gt          0.2565
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_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 0.2319(3) 0.5670(11) 0.4881(7) 0.0448(15) Uani 0.597(12) 1 d . . P A 1
S1A S 0.1864(5) 1.0137(17) 0.3988(14) 0.048(3) Uani 0.403(12) 1 d . . P A 2
O1 O 0.3777(2) 0.7372(7) 0.4895(4) 0.0277(9) Uani 1 1 d . . . . .
H1 H 0.3677 0.6444 0.5449 0.042 Uiso 1 1 calc R U . . .
O2 O 0.3706(3) 0.6216(8) 0.1340(4) 0.0325(10) Uani 1 1 d . . . . .
N1 N 0.3482(3) 0.6894(9) 0.3561(5) 0.0264(11) Uani 1 1 d . . . . .
N2 N 0.4464(3) 0.5513(10) 0.3116(6) 0.0358(13) Uani 1 1 d . . . . .
H2A H 0.4723 0.5028 0.2548 0.043 Uiso 1 1 calc R U . . .
H2B H 0.4579 0.5536 0.3999 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2412(3) 0.8078(11) 0.4005(7) 0.0313(13) Uani 1 1 d D . . . .
C9 C 0.2961(3) 0.8383(10) 0.3110(7) 0.0296(13) Uani 1 1 d . . . . .
H9 H 0.2803 0.7972 0.2153 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3893(3) 0.6222(9) 0.2633(6) 0.0254(12) Uani 1 1 d . . . . .
C10 C 0.3184(4) 1.0773(12) 0.3068(9) 0.0434(17) Uani 1 1 d . . . . .
H10A H 0.3270 1.1315 0.4005 0.065 Uiso 1 1 calc R U . . .
H10B H 0.2854 1.1643 0.2575 0.065 Uiso 1 1 calc R U . . .
H10C H 0.3566 1.0856 0.2599 0.065 Uiso 1 1 calc R U . . .
C7 C 0.1919(14) 0.959(4) 0.421(3) 0.041(6) Uani 0.597(12) 1 d D U P A 1
H7 H 0.1889 1.0989 0.3834 0.049 Uiso 0.597(12) 1 calc R U P A 1
C7A C 0.2237(18) 0.629(5) 0.476(3) 0.041(9) Uani 0.403(12) 1 d D U P A 2
H7A H 0.2467 0.4983 0.4784 0.050 Uiso 0.403(12) 1 calc R U P A 2
C6 C 0.1458(4) 0.8628(15) 0.5103(10) 0.0478(19) Uani 1 1 d . . . . .
C1 C 0.1672(4) 0.6556(14) 0.5503(9) 0.0459(18) Uani 1 1 d . . . . .
C2 C 0.1336(6) 0.533(2) 0.6409(15) 0.080(4) Uani 1 1 d . . . . .
H2 H 0.1475 0.3932 0.6683 0.096 Uiso 1 1 calc R U . . .
C3 C 0.0802(7) 0.619(4) 0.6885(16) 0.098(4) Uani 1 1 d . U . . .
H3 H 0.0585 0.5386 0.7512 0.118 Uiso 1 1 calc R U . . .
C4 C 0.0580(6) 0.818(4) 0.6468(16) 0.098(4) Uani 1 1 d . U . . .
H4 H 0.0204 0.8693 0.6789 0.117 Uiso 1 1 calc R U . . .
C5 C 0.0894(5) 0.950(3) 0.5579(16) 0.085(4) Uani 1 1 d . U . . .
H5 H 0.0743 1.0883 0.5310 0.102 Uiso 1 1 calc R U . . .
S2 S 0.81090(19) 0.5045(8) 0.5295(5) 0.0581(14) Uani 0.654(11) 1 d . . P B 1
S2A S 0.7632(5) 0.0527(15) 0.5986(12) 0.034(2) Uani 0.346(11) 1 d . . P B 2
O3 O 0.6167(2) 0.2381(8) 0.5396(4) 0.0276(9) Uani 1 1 d . . . . .
H3A H 0.6219 0.1355 0.5944 0.041 Uiso 1 1 calc R U . . .
O4 O 0.6253(3) 0.1219(7) 0.1881(5) 0.0322(10) Uani 1 1 d . . . . .
N3 N 0.6476(3) 0.1915(8) 0.4182(5) 0.0262(11) Uani 1 1 d . . . . .
N4 N 0.5488(3) 0.0509(11) 0.3334(6) 0.0397(14) Uani 1 1 d . . . . .
H4A H 0.5229 -0.0003 0.2664 0.048 Uiso 1 1 calc R U . . .
H4B H 0.5375 0.0551 0.4169 0.048 Uiso 1 1 calc R U . . .
C19 C 0.7536(3) 0.3072(11) 0.5069(7) 0.0319(14) Uani 1 1 d D . . . .
C20 C 0.6989(4) 0.3435(11) 0.3965(7) 0.0319(14) Uani 1 1 d . . . . .
H20 H 0.7143 0.3061 0.3067 0.038 Uiso 1 1 calc R U . . .
C22 C 0.6060(3) 0.1236(10) 0.3080(6) 0.0264(12) Uani 1 1 d . . . . .
C21 C 0.6764(4) 0.5815(12) 0.3864(9) 0.0455(19) Uani 1 1 d . . . . .
H21A H 0.6355 0.5889 0.3327 0.068 Uiso 1 1 calc R U . . .
H21B H 0.7068 0.6674 0.3417 0.068 Uiso 1 1 calc R U . . .
H21C H 0.6729 0.6378 0.4786 0.068 Uiso 1 1 calc R U . . .
C18A C 0.7658(11) 0.125(4) 0.586(3) 0.038(5) Uani 0.654(11) 1 d D U P B 1
H18A H 0.7397 0.0020 0.5800 0.045 Uiso 0.654(11) 1 calc R U P B 1
C18 C 0.8039(17) 0.428(6) 0.555(4) 0.066(11) Uani 0.346(11) 1 d D U P B 2
H18 H 0.8075 0.5690 0.5209 0.080 Uiso 0.346(11) 1 calc R U P B 2
C12 C 0.8278(4) 0.1455(15) 0.6854(9) 0.0475(19) Uani 1 1 d . . . . .
C17 C 0.8526(4) 0.3482(13) 0.6577(10) 0.0457(18) Uani 1 1 d . . . . .
C16 C 0.9102(5) 0.410(2) 0.7330(17) 0.083(4) Uani 1 1 d . . . . .
H16 H 0.9278 0.5457 0.7149 0.099 Uiso 1 1 calc R U . . .
C15 C 0.9404(5) 0.282(3) 0.8289(17) 0.090(4) Uani 1 1 d . . . . .
H15 H 0.9790 0.3269 0.8761 0.108 Uiso 1 1 calc R U . . .
C14 C 0.9134(6) 0.076(3) 0.8593(14) 0.089(5) Uani 1 1 d . . . . .
H14 H 0.9327 -0.0118 0.9302 0.107 Uiso 1 1 calc R U . . .
C13 C 0.8578(5) 0.0084(18) 0.7818(14) 0.065(3) Uani 1 1 d . . . . .
H13 H 0.8411 -0.1301 0.7957 0.078 Uiso 1 1 calc R U . . .
O5 O 0.4674(2) 1.0622(8) 0.5692(5) 0.0345(11) Uani 1 1 d G . . . .
H5A H 0.4521 0.9572 0.5184 0.052 Uiso 1 1 d DG U . . .
H5B H 0.4589 1.1831 0.5278 0.052 Uiso 1 1 d G U . . .
O6 O 0.5264(2) 0.5633(8) 0.5815(6) 0.0373(11) Uani 1 1 d G . . . .
H6A H 0.5468 0.6827 0.5759 0.056 Uiso 1 1 d G U . . .
H6B H 0.5502 0.4567 0.5629 0.056 Uiso 1 1 d G 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
S1 C1 1.629(11) . ?
S1 C8 1.715(9) . ?
S1A C8 1.703(12) . ?
S1A C6 1.704(15) . ?
O1 N1 1.400(6) . ?
O1 H1 0.8200 . ?
O2 C11 1.267(8) . ?
N1 C11 1.363(8) . ?
N1 C9 1.455(8) . ?
N2 C11 1.317(9) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C8 C7A 1.38(3) . ?
C8 C7 1.41(3) . ?
C8 C9 1.517(9) . ?
C9 C10 1.534(10) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 C6 1.48(3) . ?
C7 H7 0.9300 . ?
C7A C1 1.45(4) . ?
C7A H7A 0.9300 . ?
C6 C1 1.385(13) . ?
C6 C5 1.414(13) . ?
C1 C2 1.394(15) . ?
C2 C3 1.36(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.35(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.39(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
S2 C19 1.701(7) . ?
S2 C17 1.728(10) . ?
S2A C12 1.624(14) . ?
S2A C19 1.789(12) . ?
O3 N3 1.419(6) . ?
O3 H3A 0.8200 . ?
O4 C22 1.259(8) . ?
N3 C22 1.370(8) . ?
N3 C20 1.452(8) . ?
N4 C22 1.326(10) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C19 C18 1.33(3) . ?
C19 C18A 1.35(2) . ?
C19 C20 1.503(10) . ?
C20 C21 1.528(10) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18A C12 1.55(3) . ?
C18A H18A 0.9300 . ?
C18 C17 1.43(4) . ?
C18 H18 0.9300 . ?
C12 C13 1.357(15) . ?
C12 C17 1.378(12) . ?
C17 C16 1.400(13) . ?
C16 C15 1.32(2) . ?
C16 H16 0.9300 . ?
C15 C14 1.42(2) . ?
C15 H15 0.9300 . ?
C14 C13 1.38(2) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
O5 H5A 0.8499 . ?
O5 H5B 0.8499 . ?
O6 H6A 0.8502 . ?
O6 H6B 0.8504 . ?

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
C1 S1 C8 92.0(5) . . ?
C8 S1A C6 88.5(6) . . ?
N1 O1 H1 109.5 . . ?
C11 N1 O1 114.3(5) . . ?
C11 N1 C9 119.9(5) . . ?
O1 N1 C9 113.3(5) . . ?
C11 N2 H2A 120.0 . . ?
C11 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C7A C8 C9 130.6(16) . . ?
C7 C8 C9 127.4(13) . . ?
C7A C8 S1A 112.0(16) . . ?
C9 C8 S1A 117.0(6) . . ?
C7 C8 S1 111.7(12) . . ?
C9 C8 S1 120.9(5) . . ?
N1 C9 C8 110.2(5) . . ?
N1 C9 C10 112.4(6) . . ?
C8 C9 C10 112.4(6) . . ?
N1 C9 H9 107.2 . . ?
C8 C9 H9 107.2 . . ?
C10 C9 H9 107.2 . . ?
O2 C11 N2 121.9(6) . . ?
O2 C11 N1 119.2(6) . . ?
N2 C11 N1 118.8(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C7 C6 110.7(17) . . ?
C8 C7 H7 124.6 . . ?
C6 C7 H7 124.6 . . ?
C8 C7A C1 116(2) . . ?
C8 C7A H7A 121.9 . . ?
C1 C7A H7A 121.9 . . ?
C1 C6 C5 120.9(10) . . ?
C1 C6 C7 108.1(11) . . ?
C5 C6 C7 131.0(14) . . ?
C1 C6 S1A 120.0(7) . . ?
C5 C6 S1A 119.1(10) . . ?
C6 C1 C2 119.7(10) . . ?
C6 C1 C7A 103.0(13) . . ?
C2 C1 C7A 137.4(14) . . ?
C6 C1 S1 117.5(7) . . ?
C2 C1 S1 122.9(9) . . ?
C3 C2 C1 119.3(14) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 121.4(14) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 122.3(13) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 116.4(14) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C19 S2 C17 90.1(4) . . ?
C12 S2A C19 89.9(6) . . ?
N3 O3 H3A 109.5 . . ?
C22 N3 O3 112.9(5) . . ?
C22 N3 C20 120.5(5) . . ?
O3 N3 C20 113.3(5) . . ?
C22 N4 H4A 120.0 . . ?
C22 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C18 C19 C20 133.6(18) . . ?
C18A C19 C20 127.2(12) . . ?
C18A C19 S2 114.7(11) . . ?
C20 C19 S2 117.9(5) . . ?
C18 C19 S2A 105.1(18) . . ?
C20 C19 S2A 121.2(6) . . ?
N3 C20 C19 109.3(5) . . ?
N3 C20 C21 112.9(6) . . ?
C19 C20 C21 113.3(6) . . ?
N3 C20 H20 107.0 . . ?
C19 C20 H20 107.0 . . ?
C21 C20 H20 107.0 . . ?
O4 C22 N4 123.0(6) . . ?
O4 C22 N3 118.3(6) . . ?
N4 C22 N3 118.6(6) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C18A C12 112.6(16) . . ?
C19 C18A H18A 123.7 . . ?
C12 C18A H18A 123.7 . . ?
C19 C18 C17 123(3) . . ?
C19 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
C13 C12 C17 121.9(9) . . ?
C13 C12 C18A 132.9(11) . . ?
C17 C12 C18A 105.2(10) . . ?
C13 C12 S2A 116.3(8) . . ?
C17 C12 S2A 121.7(8) . . ?
C12 C17 C16 117.8(9) . . ?
C12 C17 C18 100.4(15) . . ?
C16 C17 C18 141.8(16) . . ?
C12 C17 S2 117.4(7) . . ?
C16 C17 S2 124.8(8) . . ?
C15 C16 C17 122.2(12) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C16 C15 C14 119.5(11) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C13 C14 C15 119.1(10) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C12 C13 C14 119.5(11) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
H5A O5 H5B 109.5 . . ?
H6A O6 H6B 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
C6 S1A C8 C7A 4.8(17) . . . . ?
C6 S1A C8 C9 179.1(6) . . . . ?
C1 S1 C8 C7 -0.3(14) . . . . ?
C1 S1 C8 C9 -178.8(6) . . . . ?
C11 N1 C9 C8 153.4(5) . . . . ?
O1 N1 C9 C8 -66.9(7) . . . . ?
C11 N1 C9 C10 -80.4(8) . . . . ?
O1 N1 C9 C10 59.3(7) . . . . ?
C7A C8 C9 N1 -25(2) . . . . ?
C7 C8 C9 N1 158.7(16) . . . . ?
S1A C8 C9 N1 161.8(7) . . . . ?
S1 C8 C9 N1 -23.0(8) . . . . ?
C7A C8 C9 C10 -151.4(19) . . . . ?
C7 C8 C9 C10 32.5(17) . . . . ?
S1A C8 C9 C10 35.6(9) . . . . ?
S1 C8 C9 C10 -149.3(6) . . . . ?
O1 N1 C11 O2 -164.4(5) . . . . ?
C9 N1 C11 O2 -25.1(9) . . . . ?
O1 N1 C11 N2 18.3(8) . . . . ?
C9 N1 C11 N2 157.6(6) . . . . ?
C9 C8 C7 C6 177.3(9) . . . . ?
S1 C8 C7 C6 -1(2) . . . . ?
C9 C8 C7A C1 -179.6(12) . . . . ?
S1A C8 C7A C1 -6(3) . . . . ?
C8 C7 C6 C1 2(2) . . . . ?
C8 C7 C6 C5 -179.6(13) . . . . ?
C8 S1A C6 C1 -2.6(10) . . . . ?
C8 S1A C6 C5 179.0(9) . . . . ?
C5 C6 C1 C2 -1.3(15) . . . . ?
C7 C6 C1 C2 177.1(15) . . . . ?
S1A C6 C1 C2 -179.6(10) . . . . ?
C5 C6 C1 C7A 178.1(16) . . . . ?
S1A C6 C1 C7A -0.3(17) . . . . ?
C5 C6 C1 S1 179.0(9) . . . . ?
C7 C6 C1 S1 -2.6(15) . . . . ?
C8 C7A C1 C6 4(3) . . . . ?
C8 C7A C1 C2 -176.7(13) . . . . ?
C8 S1 C1 C6 1.8(8) . . . . ?
C8 S1 C1 C2 -178.0(9) . . . . ?
C6 C1 C2 C3 -0.1(17) . . . . ?
C7A C1 C2 C3 -179(2) . . . . ?
S1 C1 C2 C3 179.7(11) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C2 C3 C4 C5 -3(3) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C1 C6 C5 C4 0.7(18) . . . . ?
C7 C6 C5 C4 -177.3(18) . . . . ?
S1A C6 C5 C4 179.1(11) . . . . ?
C17 S2 C19 C18A -3.3(12) . . . . ?
C17 S2 C19 C20 -178.5(6) . . . . ?
C12 S2A C19 C18 2(2) . . . . ?
C12 S2A C19 C20 179.0(6) . . . . ?
C22 N3 C20 C19 -152.2(6) . . . . ?
O3 N3 C20 C19 69.6(7) . . . . ?
C22 N3 C20 C21 80.8(7) . . . . ?
O3 N3 C20 C21 -57.4(7) . . . . ?
C18 C19 C20 N3 -162(3) . . . . ?
C18A C19 C20 N3 20.7(15) . . . . ?
S2 C19 C20 N3 -164.7(5) . . . . ?
S2A C19 C20 N3 22.0(9) . . . . ?
C18 C19 C20 C21 -35(3) . . . . ?
C18A C19 C20 C21 147.5(14) . . . . ?
S2 C19 C20 C21 -37.9(8) . . . . ?
S2A C19 C20 C21 148.8(7) . . . . ?
O3 N3 C22 O4 165.3(5) . . . . ?
C20 N3 C22 O4 26.9(8) . . . . ?
O3 N3 C22 N4 -18.5(8) . . . . ?
C20 N3 C22 N4 -156.8(6) . . . . ?
C20 C19 C18A C12 178.2(9) . . . . ?
S2 C19 C18A C12 3.5(19) . . . . ?
C20 C19 C18 C17 -176.0(16) . . . . ?
S2A C19 C18 C17 1(4) . . . . ?
C19 C18A C12 C13 179.3(12) . . . . ?
C19 C18A C12 C17 -1.8(18) . . . . ?
C19 S2A C12 C13 178.8(8) . . . . ?
C19 S2A C12 C17 -4.2(10) . . . . ?
C13 C12 C17 C16 -0.1(15) . . . . ?
C18A C12 C17 C16 -179.2(13) . . . . ?
S2A C12 C17 C16 -176.9(11) . . . . ?
C13 C12 C17 C18 -178(2) . . . . ?
S2A C12 C17 C18 5(2) . . . . ?
C13 C12 C17 S2 178.4(8) . . . . ?
C18A C12 C17 S2 -0.7(13) . . . . ?
C19 C18 C17 C12 -3(4) . . . . ?
C19 C18 C17 C16 179.1(18) . . . . ?
C19 S2 C17 C12 2.2(8) . . . . ?
C19 S2 C17 C16 -179.4(11) . . . . ?
C12 C17 C16 C15 -1(2) . . . . ?
C18 C17 C16 C15 177(3) . . . . ?
S2 C17 C16 C15 -179.1(13) . . . . ?
C17 C16 C15 C14 -1(3) . . . . ?
C16 C15 C14 C13 4(2) . . . . ?
C17 C12 C13 C14 2.7(16) . . . . ?
C18A C12 C13 C14 -178.5(15) . . . . ?
S2A C12 C13 C14 179.7(11) . . . . ?
C15 C14 C13 C12 -4.5(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
N2 H2B O6 0.86 2.15 2.952(8) 154.5 .
O5 H5A O1 0.85 2.06 2.790(6) 144.1 .
O6 H6B O3 0.85 1.96 2.801(7) 170.2 .
N2 H2A O6 0.86 2.15 2.990(8) 166.9 2_564
O3 H3A O4 0.82 1.81 2.619(6) 168.8 2
N4 H4A O5 0.86 2.16 3.000(8) 165.6 2_564
N4 H4B O5 0.86 2.18 2.972(8) 153.6 1_545
O1 H1 O2 0.82 1.83 2.607(6) 156.6 2_565
O6 H6A O4 0.85 2.23 2.939(7) 141.5 2_565
O5 H5B O2 0.85 2.51 2.916(7) 110.7 2_575

_refine_diff_density_max         1.142
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.144

####################################################################### 
# 
# 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_20170516nami2
_database_code_depnum_ccdc_archive 'CCDC 1589291'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_audit_creation_date             2017-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 N2 O2 S, C6 H6 N2 O'
_chemical_formula_sum            'C17 H18 N4 O3 S'
_chemical_formula_weight         358.41
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     CHNOS
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2301(19)
_cell_length_b                   10.609(2)
_cell_length_c                   17.283(3)
_cell_angle_alpha                75.429(15)
_cell_angle_beta                 74.117(15)
_cell_angle_gamma                79.223(16)
_cell_volume                     1732.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1028
_cell_measurement_temperature    213.50(10)
_cell_measurement_theta_max      73.7090
_cell_measurement_theta_min      4.3130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.874
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_av_unetI/netI     0.1784
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12307
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.341
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      213.50(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093   37.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -96.00    3.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093  125.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093   57.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
  4 omega -111.00  -20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093  -57.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093   37.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega   42.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -45.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -94.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   92.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -45.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   54.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -45.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega  105.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  125.0000    0.0000 71

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -94.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
 12 omega   30.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -30.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -94.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 14 omega   29.00  149.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -15.0000  -30.0000 120

#__ type_ start__ end____ width___ exp.time_
 15 omega   87.00  120.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771 -125.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 16 omega   81.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771   45.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771 -125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  118.00  152.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771   30.0000  -90.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0525039000
_diffrn_orient_matrix_UB_12      -0.1338924000
_diffrn_orient_matrix_UB_13      -0.0242645000
_diffrn_orient_matrix_UB_21      0.1409900000
_diffrn_orient_matrix_UB_22      0.0045906000
_diffrn_orient_matrix_UB_23      0.0143937000
_diffrn_orient_matrix_UB_31      -0.0477512000
_diffrn_orient_matrix_UB_32      -0.0702164000
_diffrn_orient_matrix_UB_33      0.0905422000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2579
_reflns_number_total             6186
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1749
_refine_ls_R_factor_gt           0.0802
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1934
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32),
  C33(H33), C34(H34)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B), N6(H6A,H6B), N8(H8A,H8B)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.64024(18) 0.53882(16) 0.22556(11) 0.0417(4) Uani 1 1 d . . . . .
S2 S 0.0601(2) 0.4840(2) 0.26689(13) 0.0604(6) Uani 1 1 d . . . . .
O1 O 0.5705(5) 0.8195(5) 0.2352(3) 0.0387(11) Uani 1 1 d . . . . .
H1 H 0.535(8) 0.876(8) 0.256(5) 0.058 Uiso 1 1 d R . . . .
O2 O 0.3838(4) 0.9017(4) 0.0838(3) 0.0400(11) Uani 1 1 d . . . . .
O3 O 0.0821(5) 0.8283(4) 0.2326(3) 0.0370(10) Uani 1 1 d . . . . .
H3A H 0.083(7) 0.916(7) 0.250(4) 0.056 Uiso 1 1 d R . . . .
O4 O -0.1208(4) 0.9163(4) 0.0889(3) 0.0415(11) Uani 1 1 d . . . . .
O5 O 0.6982(5) 0.3725(5) 0.4623(3) 0.0481(12) Uani 1 1 d . . . . .
O6 O 0.1998(5) 0.3609(5) 0.4666(3) 0.0463(12) Uani 1 1 d . . . . .
C1 C 0.6761(7) 0.4233(6) 0.1643(4) 0.0414(16) Uani 1 1 d . . . . .
C2 C 0.7951(7) 0.3326(7) 0.1535(4) 0.0493(18) Uani 1 1 d . . . . .
H2 H 0.8637 0.3267 0.1815 0.059 Uiso 1 1 calc R . . . .
C3 C 0.8061(9) 0.2534(7) 0.1002(5) 0.068(3) Uani 1 1 d . . . . .
H3 H 0.8847 0.1918 0.0913 0.081 Uiso 1 1 calc R . . . .
C4 C 0.7045(9) 0.2608(8) 0.0584(5) 0.062(2) Uani 1 1 d . . . . .
H4 H 0.7167 0.2050 0.0218 0.075 Uiso 1 1 calc R . . . .
C5 C 0.5889(8) 0.3471(7) 0.0699(4) 0.053(2) Uani 1 1 d . . . . .
H5 H 0.5201 0.3504 0.0425 0.064 Uiso 1 1 calc R . . . .
C6 C 0.5735(7) 0.4324(7) 0.1238(4) 0.0403(16) Uani 1 1 d . . . . .
C7 C 0.4653(7) 0.5323(7) 0.1448(4) 0.0404(16) Uani 1 1 d . . . . .
H7 H 0.3865 0.5510 0.1239 0.048 Uiso 1 1 calc R . . . .
C8 C 0.4847(6) 0.5977(6) 0.1970(4) 0.0352(14) Uani 1 1 d . . . . .
C9 C 0.3901(6) 0.7113(6) 0.2290(4) 0.0343(14) Uani 1 1 d . . . . .
H9 H 0.3095 0.7278 0.2049 0.041 Uiso 1 1 calc R . . . .
C10 C 0.3370(7) 0.6812(7) 0.3232(4) 0.0464(18) Uani 1 1 d . . . . .
H10A H 0.2884 0.6048 0.3402 0.070 Uiso 1 1 calc GR . . . .
H10B H 0.2754 0.7560 0.3400 0.070 Uiso 1 1 calc GR . . . .
H10C H 0.4137 0.6638 0.3488 0.070 Uiso 1 1 calc GR . . . .
C11 C 0.4720(6) 0.8973(6) 0.1193(4) 0.0310(13) Uani 1 1 d . . . . .
C12 C 0.1377(8) 0.3998(8) 0.1877(5) 0.0514(19) Uani 1 1 d . . . . .
C13 C 0.2145(9) 0.2768(8) 0.1947(6) 0.075(3) Uani 1 1 d . . . . .
H13 H 0.2338 0.2307 0.2452 0.090 Uiso 1 1 calc R . . . .
C14 C 0.2614(9) 0.2246(9) 0.1258(7) 0.084(3) Uani 1 1 d . . . . .
H14 H 0.3115 0.1403 0.1292 0.101 Uiso 1 1 calc R . . . .
C15 C 0.2353(9) 0.2960(10) 0.0505(6) 0.078(3) Uani 1 1 d . . . . .
H15 H 0.2705 0.2595 0.0035 0.094 Uiso 1 1 calc R . . . .
C16 C 0.1602(9) 0.4169(8) 0.0435(5) 0.063(2) Uani 1 1 d . . . . .
H16 H 0.1436 0.4629 -0.0077 0.076 Uiso 1 1 calc R . . . .
C17 C 0.1073(8) 0.4729(7) 0.1138(4) 0.0446(17) Uani 1 1 d . . . . .
C18 C 0.0196(7) 0.5953(6) 0.1195(4) 0.0379(15) Uani 1 1 d . . . . .
H18 H -0.0101 0.6546 0.0754 0.045 Uiso 1 1 calc R . . . .
C19 C -0.0148(6) 0.6128(6) 0.2017(4) 0.0338(14) Uani 1 1 d . . . . .
C20 C -0.1098(7) 0.7282(6) 0.2329(4) 0.0341(14) Uani 1 1 d . . . . .
H20 H -0.1895 0.7459 0.2080 0.041 Uiso 1 1 calc R . . . .
C21 C -0.1650(7) 0.7039(7) 0.3270(4) 0.0460(18) Uani 1 1 d . . . . .
H21A H -0.2141 0.6277 0.3455 0.069 Uiso 1 1 calc GR . . . .
H21B H -0.2265 0.7802 0.3416 0.069 Uiso 1 1 calc GR . . . .
H21C H -0.0891 0.6883 0.3531 0.069 Uiso 1 1 calc GR . . . .
C22 C -0.0254(7) 0.9092(6) 0.1206(4) 0.0335(14) Uani 1 1 d . . . . .
C23 C 0.8200(7) 0.3324(6) 0.4537(4) 0.0370(15) Uani 1 1 d . . . . .
C24 C 0.8851(7) 0.2184(7) 0.4118(4) 0.0393(15) Uani 1 1 d . . . . .
C25 C 1.0090(9) 0.1452(9) 0.4209(6) 0.073(3) Uani 1 1 d . . . . .
H25 H 1.0574 0.1634 0.4550 0.088 Uiso 1 1 calc R . . . .
C26 C 1.0601(10) 0.0452(10) 0.3789(6) 0.084(3) Uani 1 1 d . . . . .
H26 H 1.1473 0.0001 0.3822 0.101 Uiso 1 1 calc R . . . .
C27 C 0.8741(9) 0.0801(9) 0.3272(5) 0.062(2) Uani 1 1 d . . . . .
H27 H 0.8272 0.0582 0.2935 0.075 Uiso 1 1 calc R . . . .
C28 C 0.8120(9) 0.1843(8) 0.3652(5) 0.060(2) Uani 1 1 d . . . . .
H28 H 0.7255 0.2289 0.3596 0.072 Uiso 1 1 calc R . . . .
C29 C 0.3259(7) 0.3267(6) 0.4519(4) 0.0360(15) Uani 1 1 d . . . . .
C30 C 0.3858(6) 0.2145(6) 0.4098(4) 0.0320(13) Uani 1 1 d . . . . .
C31 C 0.3637(8) 0.0863(7) 0.4511(4) 0.0500(19) Uani 1 1 d . . . . .
H31 H 0.3127 0.0689 0.5060 0.060 Uiso 1 1 calc R . . . .
C32 C 0.4177(9) -0.0136(8) 0.4101(5) 0.061(2) Uani 1 1 d . . . . .
H32 H 0.4034 -0.0996 0.4388 0.073 Uiso 1 1 calc R . . . .
C33 C 0.5071(9) 0.1279(8) 0.2933(5) 0.059(2) Uani 1 1 d . . . . .
H33 H 0.5552 0.1429 0.2378 0.071 Uiso 1 1 calc R . . . .
C34 C 0.4598(8) 0.2346(7) 0.3291(4) 0.0507(19) Uani 1 1 d . . . . .
H34 H 0.4775 0.3194 0.2992 0.061 Uiso 1 1 calc R . . . .
N1 N 0.4529(5) 0.8341(5) 0.2042(3) 0.0341(12) Uani 1 1 d . . . . .
N2 N 0.5863(5) 0.9531(5) 0.0859(3) 0.0418(14) Uani 1 1 d . . . . .
H2A H 0.6017 0.9965 0.0350 0.050 Uiso 1 1 calc R . . . .
H2B H 0.6457 0.9462 0.1149 0.050 Uiso 1 1 calc R . . . .
N3 N -0.0408(5) 0.8474(5) 0.2056(3) 0.0320(12) Uani 1 1 d . . . . .
N4 N 0.0902(5) 0.9624(5) 0.0853(3) 0.0395(13) Uani 1 1 d . . . . .
H4A H 0.1034 1.0072 0.0348 0.047 Uiso 1 1 calc R . . . .
H4B H 0.1527 0.9522 0.1126 0.047 Uiso 1 1 calc R . . . .
N5 N 0.9920(7) 0.0090(6) 0.3338(4) 0.0523(16) Uani 1 1 d . . . . .
N6 N 0.9041(5) 0.3839(6) 0.4810(3) 0.0400(13) Uani 1 1 d . . . . .
H6A H 0.8725 0.4488 0.5061 0.048 Uiso 1 1 calc R . . . .
H6B H 0.9904 0.3525 0.4737 0.048 Uiso 1 1 calc R . . . .
N7 N 0.4893(7) 0.0039(6) 0.3321(4) 0.0520(16) Uani 1 1 d . . . . .
N8 N 0.4103(6) 0.3887(5) 0.4687(3) 0.0427(14) Uani 1 1 d . . . . .
H8A H 0.3790 0.4567 0.4909 0.051 Uiso 1 1 calc R . . . .
H8B H 0.4978 0.3620 0.4576 0.051 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 C1 1.741(7) . ?
S1 C8 1.751(6) . ?
S2 C12 1.748(8) . ?
S2 C19 1.741(6) . ?
O1 N1 1.416(7) . ?
O2 C11 1.210(7) . ?
O3 N3 1.421(6) . ?
O4 C22 1.226(7) . ?
O5 C23 1.220(8) . ?
O6 C29 1.246(8) . ?
C1 C2 1.404(10) . ?
C1 C6 1.388(9) . ?
C2 C3 1.365(10) . ?
C3 C4 1.401(12) . ?
C4 C5 1.355(11) . ?
C5 C6 1.416(9) . ?
C6 C7 1.419(9) . ?
C7 C8 1.341(9) . ?
C8 C9 1.517(9) . ?
C9 C10 1.539(8) . ?
C9 N1 1.475(8) . ?
C11 N1 1.427(7) . ?
C11 N2 1.330(8) . ?
C12 C13 1.387(11) . ?
C12 C17 1.401(10) . ?
C13 C14 1.368(12) . ?
C14 C15 1.400(13) . ?
C15 C16 1.362(12) . ?
C16 C17 1.416(10) . ?
C17 C18 1.442(10) . ?
C18 C19 1.418(8) . ?
C19 C20 1.528(9) . ?
C20 C21 1.539(8) . ?
C20 N3 1.473(8) . ?
C22 N3 1.427(7) . ?
C22 N4 1.331(8) . ?
C23 C24 1.519(9) . ?
C23 N6 1.337(8) . ?
C24 C25 1.384(11) . ?
C24 C28 1.384(10) . ?
C25 C26 1.377(12) . ?
C26 N5 1.337(10) . ?
C27 C28 1.389(11) . ?
C27 N5 1.315(10) . ?
C29 C30 1.498(9) . ?
C29 N8 1.307(8) . ?
C30 C31 1.395(9) . ?
C30 C34 1.377(9) . ?
C31 C32 1.369(10) . ?
C32 N7 1.331(10) . ?
C33 C34 1.371(10) . ?
C33 N7 1.339(10) . ?

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
C1 S1 C8 90.4(3) . . ?
C19 S2 C12 92.5(3) . . ?
C2 C1 S1 125.5(6) . . ?
C6 C1 S1 112.1(5) . . ?
C6 C1 C2 122.4(7) . . ?
C3 C2 C1 116.5(8) . . ?
C2 C3 C4 122.4(8) . . ?
C5 C4 C3 121.0(7) . . ?
C4 C5 C6 118.7(8) . . ?
C1 C6 C5 119.0(7) . . ?
C1 C6 C7 111.2(6) . . ?
C5 C6 C7 129.8(7) . . ?
C8 C7 C6 114.5(6) . . ?
C7 C8 S1 111.9(5) . . ?
C7 C8 C9 126.9(6) . . ?
C9 C8 S1 121.2(5) . . ?
C8 C9 C10 113.0(5) . . ?
N1 C9 C8 113.3(5) . . ?
N1 C9 C10 108.4(5) . . ?
O2 C11 N1 119.5(6) . . ?
O2 C11 N2 124.7(6) . . ?
N2 C11 N1 115.7(5) . . ?
C13 C12 S2 126.9(7) . . ?
C13 C12 C17 123.2(8) . . ?
C17 C12 S2 109.9(6) . . ?
C14 C13 C12 118.1(9) . . ?
C13 C14 C15 120.3(9) . . ?
C16 C15 C14 121.7(9) . . ?
C15 C16 C17 119.6(9) . . ?
C12 C17 C16 117.1(7) . . ?
C12 C17 C18 115.3(6) . . ?
C16 C17 C18 127.6(7) . . ?
C19 C18 C17 109.8(6) . . ?
C18 C19 S2 112.5(5) . . ?
C18 C19 C20 125.4(6) . . ?
C20 C19 S2 122.1(5) . . ?
C19 C20 C21 114.5(5) . . ?
N3 C20 C19 110.7(5) . . ?
N3 C20 C21 108.7(5) . . ?
O4 C22 N3 118.4(6) . . ?
O4 C22 N4 126.3(6) . . ?
N4 C22 N3 115.1(5) . . ?
O5 C23 C24 121.4(6) . . ?
O5 C23 N6 122.8(6) . . ?
N6 C23 C24 115.8(6) . . ?
C25 C24 C23 123.4(7) . . ?
C25 C24 C28 119.3(7) . . ?
C28 C24 C23 117.2(6) . . ?
C26 C25 C24 118.7(8) . . ?
N5 C26 C25 123.4(8) . . ?
N5 C27 C28 126.3(8) . . ?
C24 C28 C27 116.0(8) . . ?
O6 C29 C30 119.6(6) . . ?
O6 C29 N8 122.5(6) . . ?
N8 C29 C30 117.8(6) . . ?
C31 C30 C29 120.3(6) . . ?
C34 C30 C29 121.4(6) . . ?
C34 C30 C31 118.2(6) . . ?
C32 C31 C30 118.7(7) . . ?
N7 C32 C31 123.9(8) . . ?
N7 C33 C34 124.5(7) . . ?
C33 C34 C30 118.3(7) . . ?
O1 N1 C9 111.4(5) . . ?
O1 N1 C11 113.9(5) . . ?
C11 N1 C9 116.0(5) . . ?
O3 N3 C20 111.9(5) . . ?
O3 N3 C22 113.4(5) . . ?
C22 N3 C20 115.6(5) . . ?
C27 N5 C26 116.0(7) . . ?
C32 N7 C33 116.2(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
O1 H1 N7 0.75(7) 2.03(7) 2.756(7) 161(8) 1_565
O3 H3A N5 1.05(7) 1.89(7) 2.780(7) 140(6) 1_465
N8 H8B O5 0.87 2.10 2.890(7) 151.1 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_g170904a
_database_code_depnum_ccdc_archive 'CCDC 1589290'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_audit_creation_date             2017-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H12 N2 O2 S, 2(C6 H6 N2 O)'
_chemical_formula_sum            'C23 H24 N6 O4 S'
_chemical_formula_weight         480.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   5.1859(7)
_cell_length_b                   43.799(5)
_cell_length_c                   10.7366(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.691(12)
_cell_angle_gamma                90.00
_cell_volume                     2359.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1855
_cell_measurement_temperature    213.0
_cell_measurement_theta_max      22.8460
_cell_measurement_theta_min      4.0170
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rodlike
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.1022
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14099
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_diffrn_ambient_temperature      213.0
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   85.25   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428   57.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   39.00   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428  -37.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega   27.00   52.50   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428   19.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega  -47.00  -11.00   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428  -37.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00    0.50   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -99.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega  -17.00   16.00   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -87.0000  132.0000 44
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0472865000
_diffrn_orient_matrix_UB_12      -0.0142515000
_diffrn_orient_matrix_UB_13      0.0169984000
_diffrn_orient_matrix_UB_21      -0.0578927000
_diffrn_orient_matrix_UB_22      -0.0029818000
_diffrn_orient_matrix_UB_23      -0.0658380000
_diffrn_orient_matrix_UB_31      0.1189826000
_diffrn_orient_matrix_UB_32      -0.0070970000
_diffrn_orient_matrix_UB_33      -0.0065852000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2415
_reflns_number_total             4806
_reflns_odcompleteness_completeness 98.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0057(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4806
_refine_ls_number_restraints     65
_refine_ls_R_factor_all          0.1654
_refine_ls_R_factor_gt           0.0882
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0940P)²+1.9215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2634
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C8, C7, C6, C5, C4, C3, C2, C1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C8 \\sim C7 \\sim C6 \\sim C5 \\sim C4 \\sim C3 \\sim C2 \\sim C1: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.004
4.a Rotating group:
 N5(H5A,H5B)
4.b Ternary CH refined with riding coordinates:
 C9(H9)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4), C3(H3), C2(H2), C17(H17), C16(H16), C15(H15),
 C14(H14), C23(H23), C22(H22), C21(H21), C20(H20)
4.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B)
4.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C11 C 0.0435(8) 0.04483(10) 0.0508(4) 0.0396(11) Uani 1 d . . . .
C9 C -0.0290(9) 0.08545(10) 0.1921(5) 0.0419(12) Uani 1 d . . . .
H9 H -0.2039 0.0759 0.1827 0.050 Uiso 1 calc . . R .
C10 C -0.0721(10) 0.11987(11) 0.1895(6) 0.0578(15) Uani 1 d . . . .
H10A H -0.1316 0.1259 0.2636 0.087 Uiso 1 calc . . GR .
H10B H -0.2044 0.1254 0.1127 0.087 Uiso 1 calc . . GR .
H10C H 0.0924 0.1300 0.1906 0.087 Uiso 1 calc . . GR .
C8 C 0.1474(9) 0.07417(12) 0.3161(5) 0.0502(12) Uani 1 d . . . U
C7 C 0.0983(14) 0.05108(15) 0.3869(7) 0.0892(17) Uani 1 d . . . U
H7 H -0.0574 0.0396 0.3638 0.107 Uiso 1 calc . . R .
C6 C 0.3030(16) 0.04527(19) 0.5012(7) 0.0993(17) Uani 1 d . . . U
C5 C 0.3173(19) 0.0230(2) 0.5999(8) 0.131(2) Uani 1 d . . . U
H5 H 0.1793 0.0092 0.5959 0.157 Uiso 1 calc . . R .
C4 C 0.541(2) 0.0226(2) 0.7009(8) 0.127(2) Uani 1 d . . . U
H4 H 0.5581 0.0072 0.7620 0.152 Uiso 1 calc . . R .
C3 C 0.727(2) 0.0424(2) 0.7152(8) 0.122(2) Uani 1 d . . . U
H3 H 0.8674 0.0421 0.7889 0.147 Uiso 1 calc . . R .
C2 C 0.7203(17) 0.0637(2) 0.6237(7) 0.116(2) Uani 1 d . . . U
H2 H 0.8615 0.0773 0.6322 0.139 Uiso 1 calc . . R .
C1 C 0.5024(15) 0.06549(18) 0.5162(6) 0.0857(16) Uani 1 d . . . U
N2 N 0.2420(7) 0.03203(8) 0.0130(4) 0.0456(11) Uani 1 d . . . .
H2A H 0.2313 0.0132 -0.0107 0.055 Uiso 1 calc . . R .
H2B H 0.3817 0.0425 0.0122 0.055 Uiso 1 calc . . R .
N1 N 0.0668(7) 0.07613(8) 0.0798(4) 0.0401(10) Uani 1 d . . . .
O2 O -0.1639(6) 0.03167(7) 0.0552(4) 0.0517(10) Uani 1 d . . . .
O1 O 0.3254(5) 0.08797(7) 0.0886(3) 0.0422(8) Uani 1 d . . . .
H1 H 0.3250 0.0975 0.0227 0.063 Uiso 1 calc . . GR .
S1 S 0.4507(4) 0.09004(5) 0.38772(15) 0.0961(8) Uani 1 d . . . .
C12 C 1.1411(9) 0.24908(10) 0.2439(4) 0.0378(11) Uani 1 d . . . .
C13 C 0.9329(8) 0.22566(9) 0.2474(4) 0.0347(10) Uani 1 d . . . .
C17 C 0.7970(9) 0.21159(10) 0.1339(4) 0.0430(12) Uani 1 d . . . .
H17 H 0.8365 0.2164 0.0565 0.052 Uiso 1 calc . . R .
C16 C 0.6026(10) 0.19038(11) 0.1374(5) 0.0481(13) Uani 1 d . . . .
H16 H 0.5076 0.1809 0.0621 0.058 Uiso 1 calc . . R .
C15 C 0.5513(10) 0.18337(11) 0.2530(5) 0.0476(12) Uani 1 d . . . .
H15 H 0.4196 0.1690 0.2539 0.057 Uiso 1 calc . . R .
C14 C 0.8647(10) 0.21703(11) 0.3594(4) 0.0462(12) Uani 1 d . . . .
H14 H 0.9531 0.2265 0.4360 0.055 Uiso 1 calc . . R .
N3 N 1.2577(8) 0.26341(9) 0.3524(4) 0.0484(11) Uani 1 d . . . .
H3A H 1.3804 0.2767 0.3532 0.058 Uiso 1 calc . . R .
H3B H 1.2107 0.2594 0.4220 0.058 Uiso 1 calc . . R .
N4 N 0.6800(8) 0.19602(10) 0.3644(4) 0.0516(11) Uani 1 d . . . .
O3 O 1.2036(7) 0.25421(7) 0.1417(3) 0.0488(9) Uani 1 d . . . .
C18 C 0.7202(9) 0.18588(11) 0.7421(5) 0.0451(12) Uani 1 d . . . .
C19 C 0.9251(9) 0.16177(11) 0.7443(4) 0.0457(12) Uani 1 d . . . .
C23 C 1.0163(12) 0.15306(14) 0.6396(6) 0.0711(17) Uani 1 d . . . .
H23 H 0.9505 0.1625 0.5604 0.085 Uiso 1 calc . . R .
C22 C 1.2057(14) 0.13021(15) 0.6525(7) 0.085(2) Uani 1 d . . . .
H22 H 1.2673 0.1238 0.5826 0.103 Uiso 1 calc . . R .
C21 C 1.2989(13) 0.11736(15) 0.7716(8) 0.080(2) Uani 1 d . . . .
H21 H 1.4283 0.1022 0.7807 0.096 Uiso 1 calc . . R .
C20 C 1.0348(11) 0.14695(13) 0.8589(5) 0.0581(15) Uani 1 d . . . .
H20 H 0.9769 0.1527 0.9307 0.070 Uiso 1 calc . . R .
N5 N 0.6096(8) 0.19969(10) 0.6304(4) 0.0500(11) Uani 1 d . . . .
H5A H 0.5876 0.1867 0.5684 0.060 Uiso 1 d . . GR .
H5B H 0.4575 0.2070 0.6335 0.060 Uiso 1 d . . GR .
N6 N 1.2179(10) 0.12494(11) 0.8739(5) 0.0657(14) Uani 1 d . . . .
O4 O 0.6631(7) 0.19280(9) 0.8434(3) 0.0607(11) Uani 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
C11 N2 1.323(6) . ?
C11 N1 1.404(6) . ?
C11 O2 1.231(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.523(6) . ?
C9 C8 1.496(7) . ?
C9 N1 1.473(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 C7 1.328(8) . ?
C8 S1 1.713(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.427(9) . ?
C6 C5 1.427(11) . ?
C6 C1 1.340(10) . ?
C5 H5 0.9300 . ?
C5 C4 1.373(11) . ?
C4 H4 0.9300 . ?
C4 C3 1.275(13) . ?
C3 H3 0.9300 . ?
C3 C2 1.348(12) . ?
C2 H2 0.9300 . ?
C2 C1 1.398(9) . ?
C1 S1 1.716(7) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N1 O1 1.418(4) . ?
O1 H1 0.8200 . ?
C12 C13 1.496(6) . ?
C12 N3 1.326(5) . ?
C12 O3 1.241(5) . ?
C13 C17 1.387(6) . ?
C13 C14 1.390(6) . ?
C17 H17 0.9300 . ?
C17 C16 1.378(7) . ?
C16 H16 0.9300 . ?
C16 C15 1.369(7) . ?
C15 H15 0.9300 . ?
C15 N4 1.333(6) . ?
C14 H14 0.9300 . ?
C14 N4 1.339(6) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C18 C19 1.494(7) . ?
C18 N5 1.336(6) . ?
C18 O4 1.235(6) . ?
C19 C23 1.379(7) . ?
C19 C20 1.380(7) . ?
C23 H23 0.9300 . ?
C23 C22 1.384(8) . ?
C22 H22 0.9300 . ?
C22 C21 1.368(9) . ?
C21 H21 0.9300 . ?
C21 N6 1.315(8) . ?
C20 H20 0.9300 . ?
C20 N6 1.334(7) . ?
N5 H5A 0.8608 . ?
N5 H5B 0.8599 . ?

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
N2 C11 N1 116.9(4) . . ?
O2 C11 N2 124.6(4) . . ?
O2 C11 N1 118.4(4) . . ?
C10 C9 H9 107.0 . . ?
C8 C9 H9 107.0 . . ?
C8 C9 C10 113.4(4) . . ?
N1 C9 H9 107.0 . . ?
N1 C9 C10 109.7(4) . . ?
N1 C9 C8 112.3(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C8 S1 123.4(4) . . ?
C7 C8 C9 126.7(5) . . ?
C7 C8 S1 109.9(4) . . ?
C8 C7 H7 122.6 . . ?
C8 C7 C6 114.8(7) . . ?
C6 C7 H7 122.6 . . ?
C5 C6 C7 130.3(8) . . ?
C1 C6 C7 111.6(7) . . ?
C1 C6 C5 118.0(7) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 C6 118.0(9) . . ?
C4 C5 H5 121.0 . . ?
C5 C4 H4 118.4 . . ?
C3 C4 C5 123.2(9) . . ?
C3 C4 H4 118.4 . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.2(8) . . ?
C2 C3 H3 119.9 . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C1 120.4(9) . . ?
C1 C2 H2 119.8 . . ?
C6 C1 C2 120.0(7) . . ?
C6 C1 S1 111.1(5) . . ?
C2 C1 S1 128.9(7) . . ?
C11 N2 H2A 120.0 . . ?
C11 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C11 N1 C9 115.1(4) . . ?
C11 N1 O1 113.5(3) . . ?
O1 N1 C9 110.7(3) . . ?
N1 O1 H1 109.5 . . ?
C8 S1 C1 92.6(3) . . ?
N3 C12 C13 118.3(4) . . ?
O3 C12 C13 119.8(4) . . ?
O3 C12 N3 121.9(4) . . ?
C17 C13 C12 119.5(4) . . ?
C17 C13 C14 117.0(4) . . ?
C14 C13 C12 123.5(4) . . ?
C13 C17 H17 120.4 . . ?
C16 C17 C13 119.2(4) . . ?
C16 C17 H17 120.4 . . ?
C17 C16 H16 120.4 . . ?
C15 C16 C17 119.2(4) . . ?
C15 C16 H16 120.4 . . ?
C16 C15 H15 118.3 . . ?
N4 C15 C16 123.5(5) . . ?
N4 C15 H15 118.3 . . ?
C13 C14 H14 117.9 . . ?
N4 C14 C13 124.3(4) . . ?
N4 C14 H14 117.9 . . ?
C12 N3 H3A 120.0 . . ?
C12 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C15 N4 C14 116.8(4) . . ?
N5 C18 C19 118.4(4) . . ?
O4 C18 C19 119.2(4) . . ?
O4 C18 N5 122.4(5) . . ?
C23 C19 C18 124.9(4) . . ?
C23 C19 C20 116.6(5) . . ?
C20 C19 C18 118.5(5) . . ?
C19 C23 H23 120.0 . . ?
C19 C23 C22 120.0(5) . . ?
C22 C23 H23 120.0 . . ?
C23 C22 H22 121.2 . . ?
C21 C22 C23 117.7(6) . . ?
C21 C22 H22 121.2 . . ?
C22 C21 H21 117.8 . . ?
N6 C21 C22 124.4(6) . . ?
N6 C21 H21 117.8 . . ?
C19 C20 H20 117.7 . . ?
N6 C20 C19 124.6(6) . . ?
N6 C20 H20 117.7 . . ?
C18 N5 H5A 109.8 . . ?
C18 N5 H5B 108.9 . . ?
H5A N5 H5B 109.4 . . ?
C21 N6 C20 116.7(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
N2 H2A O2 0.86 2.03 2.887(5) 172.2 3
O1 H1 N6 0.82 1.96 2.756(5) 161.9 1_454
N3 H3A O4 0.86 2.01 2.866(5) 176.5 4_665

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
C9 C8 C7 C6 179.9(6) . . . . ?
C9 C8 S1 C1 178.5(5) . . . . ?
C10 C9 C8 C7 130.5(7) . . . . ?
C10 C9 C8 S1 -49.5(6) . . . . ?
C10 C9 N1 C11 -163.0(4) . . . . ?
C10 C9 N1 O1 66.7(4) . . . . ?
C8 C9 N1 C11 69.9(5) . . . . ?
C8 C9 N1 O1 -60.4(5) . . . . ?
C8 C7 C6 C5 178.9(9) . . . . ?
C8 C7 C6 C1 2.3(11) . . . . ?
C7 C8 S1 C1 -1.5(6) . . . . ?
C7 C6 C5 C4 -179.7(9) . . . . ?
C7 C6 C1 C2 179.2(7) . . . . ?
C7 C6 C1 S1 -3.4(9) . . . . ?
C6 C5 C4 C3 5.0(16) . . . . ?
C6 C1 S1 C8 2.9(6) . . . . ?
C5 C6 C1 C2 2.2(13) . . . . ?
C5 C6 C1 S1 179.6(7) . . . . ?
C5 C4 C3 C2 -5.2(17) . . . . ?
C4 C3 C2 C1 3.8(15) . . . . ?
C3 C2 C1 C6 -2.4(13) . . . . ?
C3 C2 C1 S1 -179.2(7) . . . . ?
C2 C1 S1 C8 179.9(8) . . . . ?
C1 C6 C5 C4 -3.3(14) . . . . ?
N2 C11 N1 C9 -140.9(4) . . . . ?
N2 C11 N1 O1 -11.9(5) . . . . ?
N1 C9 C8 C7 -104.3(7) . . . . ?
N1 C9 C8 S1 75.7(5) . . . . ?
O2 C11 N1 C9 43.1(5) . . . . ?
O2 C11 N1 O1 172.1(4) . . . . ?
S1 C8 C7 C6 -0.1(8) . . . . ?
C12 C13 C17 C16 -179.0(4) . . . . ?
C12 C13 C14 N4 -179.6(4) . . . . ?
C13 C17 C16 C15 -1.0(7) . . . . ?
C13 C14 N4 C15 -1.6(7) . . . . ?
C17 C13 C14 N4 0.7(7) . . . . ?
C17 C16 C15 N4 0.0(8) . . . . ?
C16 C15 N4 C14 1.3(7) . . . . ?
C14 C13 C17 C16 0.7(6) . . . . ?
N3 C12 C13 C17 176.3(4) . . . . ?
N3 C12 C13 C14 -3.4(6) . . . . ?
O3 C12 C13 C17 -5.0(6) . . . . ?
O3 C12 C13 C14 175.4(4) . . . . ?
C18 C19 C23 C22 -179.5(6) . . . . ?
C18 C19 C20 N6 179.7(5) . . . . ?
C19 C23 C22 C21 -1.0(10) . . . . ?
C19 C20 N6 C21 0.7(8) . . . . ?
C23 C19 C20 N6 -0.7(8) . . . . ?
C23 C22 C21 N6 1.0(11) . . . . ?
C22 C21 N6 C20 -0.8(10) . . . . ?
C20 C19 C23 C22 0.9(9) . . . . ?
N5 C18 C19 C23 2.0(8) . . . . ?
N5 C18 C19 C20 -178.4(4) . . . . ?
O4 C18 C19 C23 -176.5(5) . . . . ?
O4 C18 C19 C20 3.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
