# 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_sn
_database_code_depnum_ccdc_archive 'CCDC 1949056'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2019-08-23 deposited with the CCDC.	2019-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N2 O S'
_chemical_formula_weight         204.24

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

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

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

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

_cell_length_a                   7.3622(12)
_cell_length_b                   7.8278(13)
_cell_length_c                   9.5248(18)
_cell_angle_alpha                73.758(15)
_cell_angle_beta                 69.604(16)
_cell_angle_gamma                68.658(15)
_cell_volume                     471.81(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    437
_cell_measurement_theta_min      3.528
_cell_measurement_theta_max      23.015

_exptl_crystal_description       stick
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.307
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.04158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_reflns_number            3091
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.091
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1654
_reflns_number_gt                1015
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0803P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1654
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.1898
_refine_ls_wR_factor_gt          0.1636
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.002
_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 0.69520(17) 0.01003(13) 0.74628(12) 0.0749(5) Uani 1 1 d . . . . .
O1 O 0.6238(4) 0.7178(3) 0.5721(3) 0.0607(7) Uani 1 1 d . . . . .
N1 N 0.4486(5) 0.6280(4) 0.8111(3) 0.0700(10) Uani 1 1 d . . . . .
H1N H 0.426279 0.739850 0.805921 0.084 Uiso 1 1 calc R U . . .
N2 N 0.4807(5) 0.2703(5) 0.9104(3) 0.0710(10) Uani 1 1 d . . . . .
H2NA H 0.434678 0.384175 0.923750 0.085 Uiso 1 1 calc R U . . .
H2NB H 0.448065 0.183933 0.983699 0.085 Uiso 1 1 calc R U . . .
C1 C 0.7536(5) 0.6823(5) 0.4318(4) 0.0526(9) Uani 1 1 d . . . . .
C2 C 0.8038(6) 0.8338(6) 0.3297(5) 0.0721(12) Uani 1 1 d . . . . .
H2 H 0.753620 0.951746 0.355413 0.087 Uiso 1 1 calc R U . . .
C3 C 0.9313(7) 0.8022(7) 0.1879(5) 0.0858(15) Uani 1 1 d . . . . .
H3 H 0.965499 0.901588 0.115618 0.103 Uiso 1 1 calc R U . . .
C4 C 1.0093(7) 0.6266(8) 0.1511(5) 0.0843(15) Uani 1 1 d . . . . .
H4 H 1.096778 0.608677 0.055192 0.101 Uiso 1 1 calc R U . . .
C5 C 0.9590(5) 0.4771(7) 0.2552(4) 0.0709(12) Uani 1 1 d . . . . .
H5 H 1.010139 0.359043 0.229432 0.085 Uiso 1 1 calc R U . . .
C6 C 0.8296(5) 0.5049(5) 0.4006(4) 0.0516(9) Uani 1 1 d . . . . .
C7 C 0.7743(5) 0.3570(5) 0.5192(4) 0.0513(9) Uani 1 1 d . . . . .
H7 H 0.826775 0.235844 0.499775 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6494(4) 0.3882(5) 0.6570(4) 0.0469(8) Uani 1 1 d . . . . .
C9 C 0.5675(5) 0.5799(5) 0.6859(4) 0.0500(9) Uani 1 1 d . . . . .
C10 C 0.6010(5) 0.2282(5) 0.7779(4) 0.0512(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.664(4) . ?
O1 C9 1.367(4) . ?
O1 C1 1.378(4) . ?
N1 C9 1.270(4) . ?
N2 C10 1.313(4) . ?
C1 C6 1.372(5) . ?
C1 C2 1.383(5) . ?
C2 C3 1.378(6) . ?
C3 C4 1.377(7) . ?
C4 C5 1.379(6) . ?
C5 C6 1.403(5) . ?
C6 C7 1.440(5) . ?
C7 C8 1.342(4) . ?
C8 C9 1.466(5) . ?
C8 C10 1.502(5) . ?

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
C9 O1 C1 122.2(3) . . ?
C6 C1 O1 120.5(3) . . ?
C6 C1 C2 123.4(3) . . ?
O1 C1 C2 116.0(3) . . ?
C3 C2 C1 117.1(4) . . ?
C4 C3 C2 121.4(4) . . ?
C5 C4 C3 120.6(4) . . ?
C4 C5 C6 119.3(4) . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 118.2(3) . . ?
C5 C6 C7 123.6(4) . . ?
C8 C7 C6 122.2(3) . . ?
C7 C8 C9 118.3(3) . . ?
C7 C8 C10 120.0(3) . . ?
C9 C8 C10 121.7(3) . . ?
N1 C9 O1 117.0(3) . . ?
N1 C9 C8 124.5(3) . . ?
O1 C9 C8 118.5(3) . . ?
N2 C10 C8 116.1(3) . . ?
N2 C10 S1 121.9(3) . . ?
C8 C10 S1 121.9(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
C9 O1 C1 C6 0.9(5) . . . . ?
C9 O1 C1 C2 -177.5(3) . . . . ?
C6 C1 C2 C3 2.4(6) . . . . ?
O1 C1 C2 C3 -179.2(3) . . . . ?
C1 C2 C3 C4 -1.6(6) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
O1 C1 C6 C5 179.1(3) . . . . ?
C2 C1 C6 C5 -2.5(5) . . . . ?
O1 C1 C6 C7 -1.6(5) . . . . ?
C2 C1 C6 C7 176.8(3) . . . . ?
C4 C5 C6 C1 1.8(6) . . . . ?
C4 C5 C6 C7 -177.5(4) . . . . ?
C1 C6 C7 C8 1.1(5) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C6 C7 C8 C10 -178.4(3) . . . . ?
C1 O1 C9 N1 179.4(3) . . . . ?
C1 O1 C9 C8 0.3(5) . . . . ?
C7 C8 C9 N1 -179.8(3) . . . . ?
C10 C8 C9 N1 -1.3(5) . . . . ?
C7 C8 C9 O1 -0.8(5) . . . . ?
C10 C8 C9 O1 177.7(3) . . . . ?
C7 C8 C10 N2 178.7(3) . . . . ?
C9 C8 C10 N2 0.2(5) . . . . ?
C7 C8 C10 S1 -0.9(5) . . . . ?
C9 C8 C10 S1 -179.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2NA N1 0.86 1.93 2.643(4) 139.4 .
N2 H2NB S1 0.86 2.67 3.506(3) 164.7 2_657

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_on
_database_code_depnum_ccdc_archive 'CCDC 1949057'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2019-08-23 deposited with the CCDC.	2019-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18

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'

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

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

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

_cell_length_a                   4.7260(9)
_cell_length_b                   14.633(3)
_cell_length_c                   12.5056(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.970(14)
_cell_angle_gamma                90
_cell_volume                     862.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    402
_cell_measurement_theta_min      4.279
_cell_measurement_theta_max      20.613

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.32968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_reflns_number            8503
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_av_R_equivalents  0.1083
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.228
_diffrn_reflns_theta_max         29.996
_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             2528
_reflns_number_gt                804
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1074P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2528
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2195
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.2744
_refine_ls_wR_factor_gt          0.2096
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_restrained_S_all      0.874
_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
O1 O 0.7335(5) 0.28971(16) 0.23687(18) 0.0626(7) Uani 1 1 d . . . . .
O3 O 0.2571(5) 0.40733(16) 0.5333(2) 0.0694(8) Uani 1 1 d . . . . .
N1 N 0.4116(7) 0.4031(2) 0.2054(3) 0.0692(9) Uani 1 1 d . . . . .
H1N H 0.434677 0.385134 0.144532 0.083 Uiso 1 1 calc R U . . .
N2 N 0.1342(6) 0.4673(2) 0.3720(3) 0.0677(9) Uani 1 1 d . . . . .
H2NB H 0.012045 0.503330 0.397729 0.081 Uiso 1 1 calc R U . . .
H2NA H 0.158799 0.467976 0.304537 0.081 Uiso 1 1 calc R U . . .
C1 C 0.8780(7) 0.2282(2) 0.3036(3) 0.0528(8) Uani 1 1 d . . . . .
C2 C 1.0653(7) 0.1700(2) 0.2569(3) 0.0629(10) Uani 1 1 d . . . . .
H2 H 1.093030 0.173739 0.184101 0.075 Uiso 1 1 calc R U . . .
C3 C 1.2080(8) 0.1071(2) 0.3206(3) 0.0654(10) Uani 1 1 d . . . . .
H3 H 1.335012 0.067763 0.290482 0.078 Uiso 1 1 calc R U . . .
C4 C 1.1687(8) 0.1004(2) 0.4282(3) 0.0659(10) Uani 1 1 d . . . . .
H4 H 1.266735 0.056733 0.470175 0.079 Uiso 1 1 calc R U . . .
C5 C 0.9814(7) 0.1595(2) 0.4737(3) 0.0639(10) Uani 1 1 d . . . . .
H5 H 0.954608 0.155348 0.546501 0.077 Uiso 1 1 calc R U . . .
C6 C 0.8328(6) 0.2250(2) 0.4115(3) 0.0522(8) Uani 1 1 d . . . . .
C7 C 0.6348(6) 0.2886(2) 0.4508(3) 0.0533(8) Uani 1 1 d . . . . .
H7 H 0.603909 0.288071 0.523475 0.064 Uiso 1 1 calc R U . . .
C8 C 0.4926(6) 0.3486(2) 0.3872(3) 0.0477(8) Uani 1 1 d . . . . .
C9 C 0.5369(7) 0.3493(2) 0.2731(3) 0.0537(9) Uani 1 1 d . . . . .
C10 C 0.2842(7) 0.4109(2) 0.4363(3) 0.0546(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.373(4) . ?
O1 C1 1.377(4) . ?
O3 C10 1.229(4) . ?
N1 C9 1.272(4) . ?
N1 H1N 0.8200 . ?
N2 C10 1.324(4) . ?
N2 H2NB 0.8600 . ?
N2 H2NA 0.8600 . ?
C1 C6 1.381(5) . ?
C1 C2 1.386(4) . ?
C2 C3 1.365(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.431(4) . ?
C7 C8 1.335(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.456(4) . ?
C8 C10 1.505(4) . ?

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
C9 O1 C1 122.3(3) . . ?
C9 N1 H1N 109.5 . . ?
C10 N2 H2NB 120.0 . . ?
C10 N2 H2NA 120.0 . . ?
H2NB N2 H2NA 120.0 . . ?
O1 C1 C6 120.7(3) . . ?
O1 C1 C2 116.8(3) . . ?
C6 C1 C2 122.5(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.5(3) . . ?
C1 C6 C7 117.6(3) . . ?
C5 C6 C7 124.9(3) . . ?
C8 C7 C6 122.4(3) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 C10 118.1(3) . . ?
C9 C8 C10 122.6(3) . . ?
N1 C9 O1 117.9(3) . . ?
N1 C9 C8 124.3(3) . . ?
O1 C9 C8 117.7(3) . . ?
O3 C10 N2 122.6(3) . . ?
O3 C10 C8 119.5(3) . . ?
N2 C10 C8 117.9(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
C9 O1 C1 C6 -1.0(4) . . . . ?
C9 O1 C1 C2 178.3(3) . . . . ?
O1 C1 C2 C3 -178.8(3) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
O1 C1 C6 C5 178.5(3) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
O1 C1 C6 C7 -0.9(4) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C1 C6 C7 C8 1.0(5) . . . . ?
C5 C6 C7 C8 -178.3(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C6 C7 C8 C10 178.6(3) . . . . ?
C1 O1 C9 N1 -179.3(3) . . . . ?
C1 O1 C9 C8 2.7(4) . . . . ?
C7 C8 C9 N1 179.6(3) . . . . ?
C10 C8 C9 N1 1.8(5) . . . . ?
C7 C8 C9 O1 -2.5(4) . . . . ?
C10 C8 C9 O1 179.7(3) . . . . ?
C7 C8 C10 O3 2.4(5) . . . . ?
C9 C8 C10 O3 -179.7(3) . . . . ?
C7 C8 C10 N2 -176.9(3) . . . . ?
C9 C8 C10 N2 0.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2NA N1 0.86 2.02 2.706(4) 136.4 .
N2 H2NB O3 0.86 2.06 2.914(4) 175.9 3_566

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_oo
_database_code_depnum_ccdc_archive 'CCDC 1949059'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2019-08-23 deposited with the CCDC.	2019-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 N O3'
_chemical_formula_weight         189.17

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'

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

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

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

_cell_length_a                   4.7630(2)
_cell_length_b                   14.3440(9)
_cell_length_c                   12.3505(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.601(5)
_cell_angle_gamma                90
_cell_volume                     839.76(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1174
_cell_measurement_theta_min      4.368
_cell_measurement_theta_max      30.074

_exptl_crystal_description       stick
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_reflns_number            5565
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.289
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_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             1482
_reflns_number_gt                1209
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0649P)²+0.0671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1482
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
O1 O 0.7352(2) 0.29042(9) 0.24331(9) 0.0479(4) Uani 1 1 d . . . . .
O2 O 0.4283(3) 0.40278(9) 0.20935(10) 0.0583(4) Uani 1 1 d . . . . .
O3 O 0.2598(3) 0.40863(9) 0.53729(10) 0.0535(4) Uani 1 1 d . . . . .
N2 N 0.1325(3) 0.46713(11) 0.37127(12) 0.0512(4) Uani 1 1 d . . . . .
H2NB H 0.007655 0.503077 0.395025 0.061 Uiso 1 1 calc R U . . .
H2NA H 0.157675 0.467147 0.303258 0.061 Uiso 1 1 calc R U . . .
C1 C 0.8830(3) 0.22795(12) 0.31194(13) 0.0417(4) Uani 1 1 d . . . . .
C2 C 1.0725(4) 0.17047(13) 0.26668(16) 0.0519(5) Uani 1 1 d . . . . .
H2 H 1.098523 0.174719 0.193187 0.062 Uiso 1 1 calc R U . . .
C3 C 1.2208(4) 0.10724(14) 0.33218(18) 0.0583(6) Uani 1 1 d . . . . .
H3 H 1.348389 0.067789 0.302721 0.070 Uiso 1 1 calc R U . . .
C4 C 1.1842(4) 0.10096(14) 0.44197(19) 0.0589(6) Uani 1 1 d . . . . .
H4 H 1.286669 0.057531 0.485565 0.071 Uiso 1 1 calc R U . . .
C5 C 0.9953(4) 0.15928(13) 0.48650(16) 0.0517(5) Uani 1 1 d . . . . .
H5 H 0.971121 0.155111 0.560164 0.062 Uiso 1 1 calc R U . . .
C6 C 0.8405(3) 0.22443(11) 0.42136(13) 0.0408(4) Uani 1 1 d . . . . .
C7 C 0.6398(3) 0.28723(12) 0.45972(13) 0.0406(4) Uani 1 1 d . . . . .
H7 H 0.607621 0.285806 0.532766 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4960(3) 0.34843(11) 0.39291(13) 0.0377(4) Uani 1 1 d . . . . .
C9 C 0.5416(3) 0.35172(12) 0.27871(14) 0.0427(4) Uani 1 1 d . . . . .
C10 C 0.2861(3) 0.41173(11) 0.43945(14) 0.0406(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.376(2) . ?
O1 C1 1.378(2) . ?
O2 C9 1.213(2) . ?
O3 C10 1.228(2) . ?
N2 C10 1.325(2) . ?
N2 H2NB 0.8600 . ?
N2 H2NA 0.8600 . ?
C1 C2 1.380(2) . ?
C1 C6 1.387(2) . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.428(2) . ?
C7 C8 1.345(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.449(2) . ?
C8 C10 1.506(2) . ?

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
C9 O1 C1 122.54(13) . . ?
C10 N2 H2NB 120.0 . . ?
C10 N2 H2NA 120.0 . . ?
H2NB N2 H2NA 120.0 . . ?
O1 C1 C2 117.00(15) . . ?
O1 C1 C6 120.57(14) . . ?
C2 C1 C6 122.43(17) . . ?
C3 C2 C1 118.54(18) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.01(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.93(19) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.25(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 117.84(16) . . ?
C1 C6 C7 117.81(15) . . ?
C5 C6 C7 124.35(16) . . ?
C8 C7 C6 121.70(15) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 120.19(15) . . ?
C7 C8 C10 118.47(15) . . ?
C9 C8 C10 121.34(14) . . ?
O2 C9 O1 115.29(15) . . ?
O2 C9 C8 127.51(16) . . ?
O1 C9 C8 117.20(14) . . ?
O3 C10 N2 122.98(15) . . ?
O3 C10 C8 119.28(15) . . ?
N2 C10 C8 117.72(15) . . ?

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 O1 C1 C2 -179.65(13) . . . . ?
C9 O1 C1 C6 0.1(2) . . . . ?
O1 C1 C2 C3 -179.50(15) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
O1 C1 C6 C5 179.62(14) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
O1 C1 C6 C7 0.1(2) . . . . ?
C2 C1 C6 C7 179.84(15) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 179.68(16) . . . . ?
C1 C6 C7 C8 -0.3(2) . . . . ?
C5 C6 C7 C8 -179.79(15) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C6 C7 C8 C10 179.45(14) . . . . ?
C1 O1 C9 O2 179.79(14) . . . . ?
C1 O1 C9 C8 -0.1(2) . . . . ?
C7 C8 C9 O2 -179.98(16) . . . . ?
C10 C8 C9 O2 0.9(3) . . . . ?
C7 C8 C9 O1 -0.1(2) . . . . ?
C10 C8 C9 O1 -179.22(13) . . . . ?
C7 C8 C10 O3 2.9(2) . . . . ?
C9 C8 C10 O3 -177.88(15) . . . . ?
C7 C8 C10 N2 -175.51(15) . . . . ?
C9 C8 C10 N2 3.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2NA O2 0.86 2.04 2.7178(19) 135.4 .
N2 H2NB O3 0.86 2.03 2.8904(19) 174.6 3_566

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_so
_database_code_depnum_ccdc_archive 'CCDC 1949058'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2019-08-23 deposited with the CCDC.	2019-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 N O2 S'
_chemical_formula_weight         205.23

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

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

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

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

_cell_length_a                   11.3493(10)
_cell_length_b                   5.6476(4)
_cell_length_c                   14.2419(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.689(8)
_cell_angle_gamma                90
_cell_volume                     897.01(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1011
_cell_measurement_theta_min      3.873
_cell_measurement_theta_max      25.396

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.01614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_reflns_number            5549
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.654
_diffrn_reflns_theta_max         24.985
_diffrn_reflns_theta_full        24.985
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1576
_reflns_number_gt                1198
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0783P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1576
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.39371(6) 0.69643(13) 0.87743(4) 0.0553(3) Uani 1 1 d . . . . .
O1 O 0.44342(15) 0.1995(3) 0.58171(12) 0.0514(5) Uani 1 1 d . . . . .
O2 O 0.53276(18) 0.0669(4) 0.72034(12) 0.0639(6) Uani 1 1 d . . . . .
N2 N 0.5073(2) 0.2952(4) 0.87942(17) 0.0644(7) Uani 1 1 d . . . . .
H2NA H 0.532539 0.174084 0.852342 0.077 Uiso 1 1 calc R U . . .
H2NB H 0.522703 0.308103 0.940641 0.077 Uiso 1 1 calc R U . . .
C8 C 0.42181(19) 0.4267(4) 0.72145(15) 0.0431(6) Uani 1 1 d . . . . .
C7 C 0.3546(2) 0.5855(5) 0.66350(16) 0.0445(6) Uani 1 1 d . . . . .
H7 H 0.323930 0.716209 0.690561 0.053 Uiso 1 1 calc R U . . .
C6 C 0.3295(2) 0.5582(5) 0.56225(16) 0.0440(6) Uani 1 1 d . . . . .
C1 C 0.3752(2) 0.3624(5) 0.52332(17) 0.0452(6) Uani 1 1 d . . . . .
C10 C 0.4452(2) 0.4607(5) 0.82720(16) 0.0461(6) Uani 1 1 d . . . . .
C9 C 0.4701(2) 0.2233(5) 0.67903(19) 0.0481(6) Uani 1 1 d . . . . .
C2 C 0.3558(2) 0.3177(5) 0.42583(19) 0.0547(7) Uani 1 1 d . . . . .
H2 H 0.388400 0.185437 0.401331 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2861(2) 0.4777(6) 0.36682(18) 0.0569(7) Uani 1 1 d . . . . .
H3 H 0.271333 0.452167 0.301174 0.068 Uiso 1 1 calc R U . . .
C5 C 0.2589(2) 0.7149(5) 0.4994(2) 0.0549(7) Uani 1 1 d . . . . .
H5 H 0.226021 0.847611 0.523415 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2379(3) 0.6744(5) 0.40270(19) 0.0580(8) Uani 1 1 d . . . . .
H4 H 0.191075 0.779655 0.361429 0.070 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.667(3) . ?
O1 C9 1.369(3) . ?
O1 C1 1.378(3) . ?
O2 C9 1.215(3) . ?
N2 C10 1.315(3) . ?
N2 H2NA 0.8600 . ?
N2 H2NB 0.8600 . ?
C8 C7 1.354(3) . ?
C8 C9 1.452(4) . ?
C8 C10 1.492(3) . ?
C7 C6 1.425(3) . ?
C7 H7 0.9300 . ?
C6 C1 1.380(3) . ?
C6 C5 1.400(4) . ?
C1 C2 1.388(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C5 C4 1.373(4) . ?
C5 H5 0.9300 . ?
C4 H4 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
C9 O1 C1 122.7(2) . . ?
C10 N2 H2NA 120.0 . . ?
C10 N2 H2NB 120.0 . . ?
H2NA N2 H2NB 120.0 . . ?
C7 C8 C9 118.9(2) . . ?
C7 C8 C10 120.3(2) . . ?
C9 C8 C10 120.8(2) . . ?
C8 C7 C6 122.0(2) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C1 C6 C5 117.6(2) . . ?
C1 C6 C7 118.3(2) . . ?
C5 C6 C7 124.1(2) . . ?
O1 C1 C6 120.2(2) . . ?
O1 C1 C2 116.7(2) . . ?
C6 C1 C2 123.1(2) . . ?
N2 C10 C8 117.1(2) . . ?
N2 C10 S1 121.24(19) . . ?
C8 C10 S1 121.65(18) . . ?
O2 C9 O1 114.7(2) . . ?
O2 C9 C8 127.3(2) . . ?
O1 C9 C8 118.0(2) . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C8 C7 C6 0.3(4) . . . . ?
C10 C8 C7 C6 -179.5(2) . . . . ?
C8 C7 C6 C1 0.4(4) . . . . ?
C8 C7 C6 C5 178.8(2) . . . . ?
C9 O1 C1 C6 -0.6(3) . . . . ?
C9 O1 C1 C2 179.5(2) . . . . ?
C5 C6 C1 O1 -178.8(2) . . . . ?
C7 C6 C1 O1 -0.2(3) . . . . ?
C5 C6 C1 C2 1.1(4) . . . . ?
C7 C6 C1 C2 179.7(2) . . . . ?
C7 C8 C10 N2 177.5(2) . . . . ?
C9 C8 C10 N2 -2.3(4) . . . . ?
C7 C8 C10 S1 -1.9(3) . . . . ?
C9 C8 C10 S1 178.38(19) . . . . ?
C1 O1 C9 O2 -178.9(2) . . . . ?
C1 O1 C9 C8 1.3(3) . . . . ?
C7 C8 C9 O2 179.1(3) . . . . ?
C10 C8 C9 O2 -1.2(4) . . . . ?
C7 C8 C9 O1 -1.1(4) . . . . ?
C10 C8 C9 O1 178.7(2) . . . . ?
O1 C1 C2 C3 179.1(2) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 C6 C5 C4 -0.8(4) . . . . ?
C7 C6 C5 C4 -179.2(2) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?
C2 C3 C4 C5 0.1(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 H2NA O2 0.86 1.98 2.669(3) 136.9 .
N2 H2NB S1 0.86 2.59 3.437(2) 169.0 3_667

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.065

