# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2041000'
loop_
_audit_author_name
_audit_author_address
maoht
;Northeast Normal University
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 N O2 S'
_chemical_formula_sum            'C18 H13 N O2 S'
_chemical_formula_weight         307.35
_chemical_melting_point          ?
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0074(16)
_cell_length_b                   13.082(2)
_cell_length_c                   12.862(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.033(6)
_cell_angle_gamma                90
_cell_volume                     1470.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      50.000
_cell_measurement_theta_min      1.953
_shelx_estimated_absorpt_T_max   0.54
_shelx_estimated_absorpt_T_min   0.21
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31273
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_min         2.256
_diffrn_ambient_temperature      299.73
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2649
_reflns_number_total             3651
_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       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0766P)²+0.3625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1542
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.60014(6) 0.73017(4) 0.53892(4) 0.03677(18) Uani 1 1 d . . . . .
O2 O 0.6682(2) 0.73085(14) 0.44845(13) 0.0544(5) Uani 1 1 d . . . . .
N1 N 0.47140(19) 0.58727(15) 0.68359(13) 0.0384(4) Uani 1 1 d . . . . .
O3 O 0.5815(2) 0.82765(13) 0.58494(15) 0.0581(5) Uani 1 1 d . . . . .
C1 C 0.3774(2) 0.58624(18) 0.84618(16) 0.0406(5) Uani 1 1 d . . . . .
H1 H 0.398285 0.655818 0.854067 0.049 Uiso 1 1 calc R . . . .
C2 C 0.7039(2) 0.65152(16) 0.63867(16) 0.0339(4) Uani 1 1 d . . . . .
C3 C 0.4076(2) 0.53353(17) 0.76133(16) 0.0369(5) Uani 1 1 d . . . . .
C4 C 0.6317(2) 0.59399(16) 0.70378(15) 0.0336(4) Uani 1 1 d . . . . .
C5 C 0.4234(2) 0.66926(16) 0.50666(16) 0.0349(4) Uani 1 1 d . . . . .
C6 C 0.3727(2) 0.61360(17) 0.58494(16) 0.0362(5) Uani 1 1 d . . . . .
C7 C 0.3154(3) 0.5349(2) 0.92003(18) 0.0513(6) Uani 1 1 d . . . . .
H7 H 0.294575 0.570269 0.977583 0.062 Uiso 1 1 calc R . . . .
C8 C 0.7259(3) 0.54226(18) 0.79061(17) 0.0434(5) Uani 1 1 d . . . . .
H8 H 0.681560 0.502917 0.835248 0.052 Uiso 1 1 calc R . . . .
C9 C 0.8639(2) 0.65604(18) 0.65901(19) 0.0446(5) Uani 1 1 d . . . . .
H9 H 0.909861 0.693597 0.613972 0.054 Uiso 1 1 calc R . . . .
C10 C 0.3261(3) 0.68911(19) 0.40626(17) 0.0444(5) Uani 1 1 d . . . . .
H10 H 0.363381 0.723867 0.354814 0.053 Uiso 1 1 calc R . . . .
C11 C 0.8827(3) 0.54874(19) 0.81087(19) 0.0481(6) Uani 1 1 d . . . . .
H11 H 0.942752 0.514633 0.869665 0.058 Uiso 1 1 calc R . . . .
C12 C 0.2181(3) 0.5854(2) 0.55999(19) 0.0506(6) Uani 1 1 d . . . . .
H12 H 0.178841 0.550747 0.610568 0.061 Uiso 1 1 calc R . . . .
C13 C 0.9526(3) 0.6053(2) 0.7451(2) 0.0513(6) Uani 1 1 d . . . . .
H13 H 1.058763 0.608738 0.759147 0.062 Uiso 1 1 calc R . . . .
C14 C 0.2846(3) 0.4325(2) 0.9089(2) 0.0572(7) Uani 1 1 d . . . . .
H14 H 0.242643 0.398601 0.958507 0.069 Uiso 1 1 calc R . . . .
C15 C 0.1233(3) 0.6083(2) 0.4614(2) 0.0576(7) Uani 1 1 d . . . . .
H15 H 0.020630 0.589870 0.447316 0.069 Uiso 1 1 calc R . . . .
C16 C 0.3781(3) 0.4298(2) 0.7498(2) 0.0563(7) Uani 1 1 d . . . . .
H16 H 0.399848 0.393876 0.692811 0.068 Uiso 1 1 calc R . . . .
C17 C 0.1770(3) 0.6580(2) 0.3829(2) 0.0538(6) Uani 1 1 d . . . . .
H17 H 0.112843 0.670041 0.315620 0.065 Uiso 1 1 calc R . . . .
C18 C 0.3156(3) 0.3802(2) 0.8244(2) 0.0647(7) Uani 1 1 d . . . . .
H18 H 0.294605 0.310581 0.817080 0.078 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4406(16) . ?
S1 O3 1.4328(18) . ?
S1 C2 1.731(2) . ?
S1 C5 1.738(2) . ?
N1 C3 1.450(2) . ?
N1 C4 1.407(3) . ?
N1 C6 1.404(3) . ?
C1 C3 1.373(3) . ?
C1 C7 1.387(3) . ?
C2 C4 1.398(3) . ?
C2 C9 1.402(3) . ?
C3 C16 1.384(3) . ?
C4 C8 1.402(3) . ?
C5 C6 1.405(3) . ?
C5 C10 1.398(3) . ?
C6 C12 1.401(3) . ?
C7 C14 1.368(4) . ?
C8 C11 1.376(3) . ?
C9 C13 1.369(3) . ?
C10 C17 1.365(3) . ?
C11 C13 1.385(3) . ?
C12 C15 1.379(3) . ?
C14 C18 1.369(4) . ?
C15 C17 1.383(4) . ?
C16 C18 1.386(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
O2 S1 C2 110.08(10) . . ?
O2 S1 C5 110.75(10) . . ?
O3 S1 O2 116.34(11) . . ?
O3 S1 C2 108.62(10) . . ?
O3 S1 C5 108.30(11) . . ?
C2 S1 C5 101.72(10) . . ?
C4 N1 C3 117.62(16) . . ?
C6 N1 C3 118.19(16) . . ?
C6 N1 C4 123.23(16) . . ?
C3 C1 C7 119.4(2) . . ?
C4 C2 S1 121.20(15) . . ?
C4 C2 C9 121.1(2) . . ?
C9 C2 S1 117.32(16) . . ?
C1 C3 N1 119.5(2) . . ?
C1 C3 C16 120.5(2) . . ?
C16 C3 N1 119.9(2) . . ?
C2 C4 N1 121.93(18) . . ?
C2 C4 C8 117.24(19) . . ?
C8 C4 N1 120.83(18) . . ?
C6 C5 S1 120.27(16) . . ?
C10 C5 S1 117.90(16) . . ?
C10 C5 C6 121.2(2) . . ?
N1 C6 C5 122.03(18) . . ?
C12 C6 N1 121.24(19) . . ?
C12 C6 C5 116.7(2) . . ?
C14 C7 C1 120.5(2) . . ?
C11 C8 C4 121.1(2) . . ?
C13 C9 C2 120.2(2) . . ?
C17 C10 C5 120.7(2) . . ?
C8 C11 C13 121.0(2) . . ?
C15 C12 C6 120.8(2) . . ?
C9 C13 C11 119.3(2) . . ?
C7 C14 C18 119.9(2) . . ?
C12 C15 C17 121.7(2) . . ?
C3 C16 C18 119.0(2) . . ?
C10 C17 C15 118.6(2) . . ?
C14 C18 C16 120.7(3) . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2041003'
loop_
_audit_author_name
_audit_author_address
maoht
;Northeast Normal University
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O2 S'
_chemical_formula_sum            'C20 H17 N O2 S'
_chemical_formula_weight         335.40
_chemical_melting_point          ?
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.2656(5)
_cell_length_b                   18.9739(11)
_cell_length_c                   12.0131(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.825(4)
_cell_angle_gamma                90
_cell_volume                     1652.40(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8473
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      50.000
_cell_measurement_theta_min      1.953
_shelx_estimated_absorpt_T_max   0.54
_shelx_estimated_absorpt_T_min   0.21
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20760
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.009
_diffrn_reflns_theta_min         2.738
_diffrn_ambient_temperature      292.49
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2462
_reflns_number_total             3244
_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       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.083
_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)+(0.0583P)²+0.7474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.71376(8) 0.46565(3) 0.69725(5) 0.0494(2) Uani 1 1 d . . . . .
N1 N 0.5130(2) 0.33228(8) 0.61915(14) 0.0321(4) Uani 1 1 d . . . . .
O1 O 0.8755(2) 0.43450(13) 0.75159(18) 0.0800(6) Uani 1 1 d . . . . .
O2 O 0.7029(3) 0.54131(9) 0.69806(19) 0.0791(7) Uani 1 1 d . . . . .
C1 C 0.4524(3) 0.36402(10) 0.71508(16) 0.0315(4) Uani 1 1 d . . . . .
C2 C 0.4524(3) 0.26099(10) 0.59446(16) 0.0314(4) Uani 1 1 d . . . . .
C3 C 0.6093(3) 0.36803(10) 0.53953(17) 0.0322(4) Uani 1 1 d . . . . .
C4 C 0.5213(3) 0.42927(11) 0.75417(18) 0.0372(5) Uani 1 1 d . . . . .
C5 C 0.5667(3) 0.20604(11) 0.63287(17) 0.0400(5) Uani 1 1 d . . . . .
C6 C 0.6895(3) 0.43418(11) 0.56165(19) 0.0373(5) Uani 1 1 d . . . . .
C7 C 0.2820(3) 0.25032(11) 0.53547(18) 0.0401(5) Uani 1 1 d . . . . .
C8 C 0.3144(3) 0.33258(12) 0.77445(18) 0.0414(5) Uani 1 1 d . . . . .
H8 H 0.268489 0.288614 0.752573 0.050 Uiso 1 1 calc R . . . .
C9 C 0.6242(3) 0.33962(12) 0.43275(19) 0.0420(5) Uani 1 1 d . . . . .
H9 H 0.574176 0.295497 0.415674 0.050 Uiso 1 1 calc R . . . .
C10 C 0.4483(4) 0.46261(12) 0.8448(2) 0.0497(6) Uani 1 1 d . . . . .
H10 H 0.492906 0.506525 0.868027 0.060 Uiso 1 1 calc R . . . .
C11 C 0.3114(4) 0.43096(13) 0.8997(2) 0.0539(6) Uani 1 1 d . . . . .
H11 H 0.262669 0.453174 0.960135 0.065 Uiso 1 1 calc R . . . .
C12 C 0.5038(4) 0.13714(12) 0.6103(2) 0.0532(7) Uani 1 1 d . . . . .
H12 H 0.574703 0.098867 0.635737 0.064 Uiso 1 1 calc R . . . .
C13 C 0.7732(3) 0.47153(13) 0.4781(2) 0.0505(6) Uani 1 1 d . . . . .
H13 H 0.821101 0.516221 0.493217 0.061 Uiso 1 1 calc R . . . .
C14 C 0.2462(3) 0.36589(13) 0.86454(19) 0.0484(6) Uani 1 1 d . . . . .
H14 H 0.154371 0.344117 0.902537 0.058 Uiso 1 1 calc R . . . .
C15 C 0.7122(3) 0.37643(14) 0.3528(2) 0.0528(6) Uani 1 1 d . . . . .
H15 H 0.722860 0.356240 0.283027 0.063 Uiso 1 1 calc R . . . .
C16 C 0.2289(4) 0.18099(13) 0.5136(2) 0.0559(7) Uani 1 1 d . . . . .
H16 H 0.117862 0.171953 0.473152 0.067 Uiso 1 1 calc R . . . .
C17 C 0.7850(3) 0.44281(14) 0.3744(2) 0.0570(7) Uani 1 1 d . . . . .
H17 H 0.841270 0.467562 0.319116 0.068 Uiso 1 1 calc R . . . .
C18 C 0.3377(4) 0.12598(13) 0.5508(2) 0.0615(8) Uani 1 1 d . . . . .
H18 H 0.298801 0.080073 0.535656 0.074 Uiso 1 1 calc R . . . .
C19 C 0.1607(3) 0.31094(14) 0.4971(2) 0.0584(7) Uani 1 1 d . . . . .
H19A H 0.116280 0.334517 0.560704 0.088 Uiso 1 1 calc GR . . . .
H19B H 0.057921 0.293588 0.450597 0.088 Uiso 1 1 calc GR . . . .
H19C H 0.230316 0.343448 0.455328 0.088 Uiso 1 1 calc GR . . . .
C20 C 0.7510(4) 0.21963(16) 0.6930(2) 0.0637(7) Uani 1 1 d . . . . .
H20A H 0.833316 0.239283 0.641980 0.096 Uiso 1 1 calc GR . . . .
H20B H 0.800945 0.176132 0.722522 0.096 Uiso 1 1 calc GR . . . .
H20C H 0.736549 0.252177 0.752988 0.096 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4332(19) . ?
S1 O2 1.4378(19) . ?
S1 C4 1.740(2) . ?
S1 C6 1.733(2) . ?
N1 C1 1.397(2) . ?
N1 C2 1.447(2) . ?
N1 C3 1.398(2) . ?
C1 C4 1.404(3) . ?
C1 C8 1.401(3) . ?
C2 C5 1.393(3) . ?
C2 C7 1.400(3) . ?
C3 C6 1.402(3) . ?
C3 C9 1.402(3) . ?
C4 C10 1.394(3) . ?
C5 C12 1.405(3) . ?
C5 C20 1.501(4) . ?
C6 C13 1.400(3) . ?
C7 C16 1.391(3) . ?
C7 C19 1.503(3) . ?
C8 C14 1.374(3) . ?
C9 C15 1.378(3) . ?
C10 C11 1.369(4) . ?
C11 C14 1.378(4) . ?
C12 C18 1.377(4) . ?
C13 C17 1.367(4) . ?
C15 C17 1.384(4) . ?
C16 C18 1.366(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
O1 S1 O2 116.89(14) . . ?
O1 S1 C4 108.27(12) . . ?
O1 S1 C6 108.35(12) . . ?
O2 S1 C4 110.35(12) . . ?
O2 S1 C6 110.38(12) . . ?
C6 S1 C4 101.46(10) . . ?
C1 N1 C2 117.63(15) . . ?
C1 N1 C3 123.70(16) . . ?
C3 N1 C2 118.21(16) . . ?
N1 C1 C4 122.07(18) . . ?
N1 C1 C8 120.77(18) . . ?
C8 C1 C4 117.13(19) . . ?
C5 C2 N1 117.73(18) . . ?
C5 C2 C7 123.20(19) . . ?
C7 C2 N1 119.06(18) . . ?
N1 C3 C6 121.70(19) . . ?
N1 C3 C9 120.79(18) . . ?
C6 C3 C9 117.47(19) . . ?
C1 C4 S1 119.75(16) . . ?
C10 C4 S1 118.96(17) . . ?
C10 C4 C1 121.0(2) . . ?
C2 C5 C12 117.0(2) . . ?
C2 C5 C20 121.6(2) . . ?
C12 C5 C20 121.4(2) . . ?
C3 C6 S1 120.12(16) . . ?
C13 C6 S1 118.54(17) . . ?
C13 C6 C3 120.8(2) . . ?
C2 C7 C19 121.71(19) . . ?
C16 C7 C2 117.2(2) . . ?
C16 C7 C19 121.1(2) . . ?
C14 C8 C1 120.9(2) . . ?
C15 C9 C3 120.7(2) . . ?
C11 C10 C4 120.2(2) . . ?
C10 C11 C14 119.4(2) . . ?
C18 C12 C5 120.4(2) . . ?
C17 C13 C6 120.5(2) . . ?
C8 C14 C11 121.2(2) . . ?
C9 C15 C17 121.3(2) . . ?
C18 C16 C7 120.9(2) . . ?
C13 C17 C15 119.1(2) . . ?
C16 C18 C12 121.3(2) . . ?

_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_maoht190627_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2041002'
loop_
_audit_author_name
_audit_author_address
maoht
;Northeast Normal University
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-27
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O2 S'
_chemical_formula_sum            'C19 H15 N O2 S'
_chemical_formula_weight         321.38
_chemical_melting_point          ?
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9570(12)
_cell_length_b                   14.1439(17)
_cell_length_c                   12.4792(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.209(4)
_cell_angle_gamma                90
_cell_volume                     1539.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7417
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      50.000
_cell_measurement_theta_min      1.953
_shelx_estimated_absorpt_T_max   0.54
_shelx_estimated_absorpt_T_min   0.21
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14528
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.079
_diffrn_reflns_theta_max         25.079
_diffrn_reflns_theta_min         2.880
_diffrn_ambient_temperature      172.99
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2218
_reflns_number_total             2726
_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       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.142
_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)+(0.0302P)²+4.0756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1465
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.62255(11) 0.27779(6) 0.53700(7) 0.0297(2) Uani 1 1 d . . . . .
O1 O 0.6937(3) 0.27324(19) 0.4445(2) 0.0397(7) Uani 1 1 d . . . . .
O2 O 0.6050(3) 0.18967(17) 0.5909(2) 0.0401(7) Uani 1 1 d . . . . .
N1 N 0.4862(3) 0.41590(19) 0.6761(2) 0.0248(6) Uani 1 1 d . . . . .
C1 C 0.2884(4) 0.5351(3) 0.9187(3) 0.0316(8) Uani 1 1 d . . . . .
H1 H 0.243084 0.561342 0.973742 0.038 Uiso 1 1 calc R . . . .
C2 C 0.3325(4) 0.4418(3) 0.9269(3) 0.0342(8) Uani 1 1 d . . . . .
H2 H 0.318501 0.404604 0.987285 0.041 Uiso 1 1 calc R . . . .
C3 C 0.3977(4) 0.4020(2) 0.8463(3) 0.0288(8) Uani 1 1 d . . . . .
H3 H 0.428518 0.337582 0.850881 0.035 Uiso 1 1 calc R . . . .
C4 C 0.4171(4) 0.4580(2) 0.7593(3) 0.0252(7) Uani 1 1 d . . . . .
C5 C 0.3911(4) 0.3894(2) 0.5750(3) 0.0233(7) Uani 1 1 d . . . . .
C6 C 0.4445(4) 0.3324(2) 0.4997(3) 0.0255(7) Uani 1 1 d . . . . .
C7 C 0.3505(5) 0.3080(3) 0.3986(3) 0.0353(9) Uani 1 1 d . . . . .
H7 H 0.389997 0.270354 0.348440 0.042 Uiso 1 1 calc R . . . .
C8 C 0.2005(5) 0.3382(3) 0.3709(3) 0.0394(9) Uani 1 1 d . . . . .
H8 H 0.135927 0.321759 0.301885 0.047 Uiso 1 1 calc R . . . .
C9 C 0.2590(5) 0.6933(3) 0.8247(4) 0.0449(10) Uani 1 1 d . . . . .
H9A H 0.147501 0.696898 0.815340 0.067 Uiso 1 1 calc GR . . . .
H9B H 0.288166 0.722662 0.761394 0.067 Uiso 1 1 calc GR . . . .
H9C H 0.309302 0.726602 0.892169 0.067 Uiso 1 1 calc GR . . . .
C10 C 0.3079(4) 0.5919(2) 0.8328(3) 0.0290(8) Uani 1 1 d . . . . .
C11 C 0.3758(4) 0.5519(2) 0.7527(3) 0.0280(8) Uani 1 1 d . . . . .
H11 H 0.393230 0.589624 0.693830 0.034 Uiso 1 1 calc R . . . .
C12 C 0.6462(4) 0.4113(2) 0.6973(3) 0.0233(7) Uani 1 1 d . . . . .
C13 C 0.7232(4) 0.3560(2) 0.6341(3) 0.0247(7) Uani 1 1 d . . . . .
C14 C 0.8826(4) 0.3546(3) 0.6545(3) 0.0341(8) Uani 1 1 d . . . . .
H14 H 0.932296 0.317582 0.609445 0.041 Uiso 1 1 calc R . . . .
C15 C 0.9686(4) 0.4070(3) 0.7399(3) 0.0373(9) Uani 1 1 d . . . . .
H15 H 1.077390 0.405860 0.754482 0.045 Uiso 1 1 calc R . . . .
C16 C 0.8942(4) 0.4614(3) 0.8041(3) 0.0355(9) Uani 1 1 d . . . . .
H16 H 0.953153 0.497286 0.863253 0.043 Uiso 1 1 calc R . . . .
C17 C 0.7366(4) 0.4645(3) 0.7838(3) 0.0307(8) Uani 1 1 d . . . . .
H17 H 0.688259 0.502892 0.828403 0.037 Uiso 1 1 calc R . . . .
C18 C 0.2376(4) 0.4190(3) 0.5453(3) 0.0304(8) Uani 1 1 d . . . . .
H18 H 0.197218 0.457273 0.594507 0.036 Uiso 1 1 calc R . . . .
C19 C 0.1450(4) 0.3932(3) 0.4457(3) 0.0355(9) Uani 1 1 d . . . . .
H19 H 0.041073 0.413293 0.427678 0.043 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.442(2) . ?
S1 O2 1.442(3) . ?
S1 C6 1.737(3) . ?
S1 C13 1.733(3) . ?
N1 C4 1.452(4) . ?
N1 C5 1.403(4) . ?
N1 C12 1.398(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.375(5) . ?
C1 C10 1.382(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(5) . ?
C4 C11 1.376(5) . ?
C5 C6 1.402(4) . ?
C5 C18 1.403(5) . ?
C6 C7 1.391(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(5) . ?
C8 H8 0.9500 . ?
C8 C19 1.391(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C10 1.496(5) . ?
C10 C11 1.402(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(4) . ?
C12 C17 1.410(5) . ?
C13 C14 1.392(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.377(5) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 116.76(16) . . ?
O1 S1 C6 110.62(16) . . ?
O1 S1 C13 109.50(17) . . ?
O2 S1 C6 108.55(17) . . ?
O2 S1 C13 108.64(16) . . ?
C13 S1 C6 101.68(16) . . ?
C5 N1 C4 118.8(3) . . ?
C12 N1 C4 118.0(3) . . ?
C12 N1 C5 122.9(3) . . ?
C2 C1 H1 119.0 . . ?
C2 C1 C10 122.1(3) . . ?
C10 C1 H1 119.0 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 N1 118.4(3) . . ?
C11 C4 N1 120.4(3) . . ?
C11 C4 C3 121.2(3) . . ?
N1 C5 C18 120.9(3) . . ?
C6 C5 N1 121.8(3) . . ?
C6 C5 C18 117.3(3) . . ?
C5 C6 S1 120.6(2) . . ?
C7 C6 S1 117.5(3) . . ?
C7 C6 C5 121.4(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C19 118.9(3) . . ?
C19 C8 H8 120.6 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
C1 C10 C9 121.5(3) . . ?
C1 C10 C11 118.0(3) . . ?
C11 C10 C9 120.5(3) . . ?
C4 C11 C10 120.1(3) . . ?
C4 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
N1 C12 C13 122.4(3) . . ?
N1 C12 C17 120.3(3) . . ?
C13 C12 C17 117.3(3) . . ?
C12 C13 S1 120.4(3) . . ?
C14 C13 S1 117.8(3) . . ?
C14 C13 C12 121.5(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C5 C18 H18 119.6 . . ?
C19 C18 C5 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C8 C19 H19 119.3 . . ?
C18 C19 C8 121.4(4) . . ?
C18 C19 H19 119.3 . . ?

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
S1 C6 C7 C8 170.8(3) . . . . ?
S1 C13 C14 C15 -172.2(3) . . . . ?
O1 S1 C6 C5 -145.4(3) . . . . ?
O1 S1 C6 C7 42.4(3) . . . . ?
O1 S1 C13 C12 145.8(3) . . . . ?
O1 S1 C13 C14 -40.6(3) . . . . ?
O2 S1 C6 C5 85.2(3) . . . . ?
O2 S1 C6 C7 -86.9(3) . . . . ?
O2 S1 C13 C12 -85.6(3) . . . . ?
O2 S1 C13 C14 88.0(3) . . . . ?
N1 C4 C11 C10 179.5(3) . . . . ?
N1 C5 C6 S1 9.6(4) . . . . ?
N1 C5 C6 C7 -178.6(3) . . . . ?
N1 C5 C18 C19 179.7(3) . . . . ?
N1 C12 C13 S1 -8.6(4) . . . . ?
N1 C12 C13 C14 178.0(3) . . . . ?
N1 C12 C17 C16 -179.0(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C10 C11 C4 1.7(5) . . . . ?
C2 C1 C10 C9 179.8(4) . . . . ?
C2 C1 C10 C11 -0.3(5) . . . . ?
C2 C3 C4 N1 179.6(3) . . . . ?
C2 C3 C4 C11 1.3(5) . . . . ?
C3 C4 C11 C10 -2.2(5) . . . . ?
C4 N1 C5 C6 -167.4(3) . . . . ?
C4 N1 C5 C18 12.4(5) . . . . ?
C4 N1 C12 C13 166.8(3) . . . . ?
C4 N1 C12 C17 -14.2(4) . . . . ?
C5 N1 C4 C3 102.3(4) . . . . ?
C5 N1 C4 C11 -79.4(4) . . . . ?
C5 N1 C12 C13 -18.8(5) . . . . ?
C5 N1 C12 C17 160.1(3) . . . . ?
C5 C6 C7 C8 -1.3(6) . . . . ?
C5 C18 C19 C8 -0.8(6) . . . . ?
C6 S1 C13 C12 28.7(3) . . . . ?
C6 S1 C13 C14 -157.6(3) . . . . ?
C6 C5 C18 C19 -0.5(5) . . . . ?
C6 C7 C8 C19 -0.1(6) . . . . ?
C7 C8 C19 C18 1.1(6) . . . . ?
C9 C10 C11 C4 -178.4(3) . . . . ?
C10 C1 C2 C3 -0.6(5) . . . . ?
C12 N1 C4 C3 -83.1(4) . . . . ?
C12 N1 C4 C11 95.2(4) . . . . ?
C12 N1 C5 C6 18.3(5) . . . . ?
C12 N1 C5 C18 -161.9(3) . . . . ?
C12 C13 C14 C15 1.3(5) . . . . ?
C13 S1 C6 C5 -29.2(3) . . . . ?
C13 S1 C6 C7 158.7(3) . . . . ?
C13 C12 C17 C16 0.0(5) . . . . ?
C13 C14 C15 C16 -0.6(6) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C15 C16 C17 C12 0.7(6) . . . . ?
C17 C12 C13 S1 172.4(2) . . . . ?
C17 C12 C13 C14 -1.0(5) . . . . ?
C18 C5 C6 S1 -170.3(3) . . . . ?
C18 C5 C6 C7 1.5(5) . . . . ?

_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_maoht190508_1_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2041001'
loop_
_audit_author_name
_audit_author_address
maoht
;Northeast Normal University
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O2 S'
_chemical_formula_sum            'C19 H15 N O2 S'
_chemical_formula_weight         321.38
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.4141(12)
_cell_length_b                   19.321(3)
_cell_length_c                   8.6620(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.449(5)
_cell_angle_gamma                90
_cell_volume                     1518.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9300
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      50.000
_cell_measurement_theta_min      1.953
_shelx_estimated_absorpt_T_max   0.54
_shelx_estimated_absorpt_T_min   0.21
_exptl_absorpt_coefficient_mu    1.967
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13702
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.279
_diffrn_reflns_theta_min         4.577
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2686
_reflns_number_total             2986
_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       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.5796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15), C19(H19)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.59360(4) 0.60559(2) 0.68033(5) 0.03672(14) Uani 1 1 d . . . . .
O1 O 0.69877(16) 0.55316(9) 0.75206(18) 0.0654(4) Uani 1 1 d . . . . .
O2 O 0.61046(17) 0.67099(8) 0.76123(17) 0.0580(4) Uani 1 1 d . . . . .
N1 N 0.32416(13) 0.61925(7) 0.38684(15) 0.0298(3) Uani 1 1 d . . . . .
C1 C 0.2492(2) 0.53022(11) 0.8028(2) 0.0519(5) Uani 1 1 d . . . . .
H1 H 0.231969 0.509068 0.892537 0.062 Uiso 1 1 calc R . . . .
C2 C 0.1332(2) 0.54717(10) 0.6722(2) 0.0471(4) Uani 1 1 d . . . . .
H2 H 0.037191 0.538349 0.676404 0.056 Uiso 1 1 calc R . . . .
C3 C 0.15663(18) 0.57669(9) 0.5368(2) 0.0385(4) Uani 1 1 d . . . . .
H3 H 0.076394 0.587068 0.450916 0.046 Uiso 1 1 calc R . . . .
C4 C 0.29976(17) 0.59145(8) 0.52592(18) 0.0287(3) Uani 1 1 d . . . . .
C5 C 0.19830(16) 0.64290(8) 0.26201(17) 0.0290(3) Uani 1 1 d . . . . .
C6 C 0.11404(18) 0.59518(10) 0.1570(2) 0.0376(4) Uani 1 1 d . . . . .
H6 H 0.138681 0.548464 0.166072 0.045 Uiso 1 1 calc R . . . .
C7 C -0.00749(19) 0.61767(11) 0.0381(2) 0.0454(5) Uani 1 1 d . . . . .
H7 H -0.064533 0.586065 -0.033032 0.054 Uiso 1 1 calc R . . . .
C8 C -0.04308(18) 0.68683(12) 0.0262(2) 0.0480(5) Uani 1 1 d . . . . .
H8 H -0.125181 0.701970 -0.052253 0.058 Uiso 1 1 calc R . . . .
C9 C 0.7422(2) 0.64446(12) 0.3042(3) 0.0542(5) Uani 1 1 d . . . . .
H9 H 0.833862 0.651446 0.285225 0.065 Uiso 1 1 calc R . . . .
C10 C 0.73186(19) 0.62680(11) 0.4531(2) 0.0474(5) Uani 1 1 d . . . . .
H10 H 0.817110 0.620485 0.535708 0.057 Uiso 1 1 calc R . . . .
C11 C 0.59456(17) 0.61813(8) 0.48254(19) 0.0328(3) Uani 1 1 d . . . . .
C12 C 0.46381(16) 0.62595(8) 0.36085(18) 0.0291(3) Uani 1 1 d . . . . .
C13 C 0.47802(19) 0.64199(9) 0.2074(2) 0.0383(4) Uani 1 1 d . . . . .
H13 H 0.393873 0.645951 0.122399 0.046 Uiso 1 1 calc R . . . .
C14 C 0.6136(2) 0.65188(11) 0.1809(2) 0.0474(5) Uani 1 1 d . . . . .
H14 H 0.619867 0.663760 0.078893 0.057 Uiso 1 1 calc R . . . .
C15 C 0.3896(2) 0.54527(10) 0.7968(2) 0.0457(4) Uani 1 1 d . . . . .
H15 H 0.468696 0.534694 0.883813 0.055 Uiso 1 1 calc R . . . .
C16 C 0.41533(17) 0.57631(8) 0.66155(18) 0.0324(3) Uani 1 1 d . . . . .
C17 C 0.16648(16) 0.71314(9) 0.25030(18) 0.0321(3) Uani 1 1 d . . . . .
C18 C 0.2634(2) 0.76499(10) 0.3573(2) 0.0446(4) Uani 1 1 d . . . . .
H18A H 0.289627 0.748166 0.465498 0.067 Uiso 1 1 calc GR . . . .
H18B H 0.211608 0.808077 0.352269 0.067 Uiso 1 1 calc GR . . . .
H18C H 0.351140 0.771943 0.322716 0.067 Uiso 1 1 calc GR . . . .
C19 C 0.04266(19) 0.73370(10) 0.1302(2) 0.0432(4) Uani 1 1 d . . . . .
H19 H 0.017473 0.780344 0.120187 0.052 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4370(14) . ?
S1 O2 1.4331(15) . ?
S1 C11 1.7326(17) . ?
S1 C16 1.7371(17) . ?
N1 C4 1.393(2) . ?
N1 C5 1.4489(18) . ?
N1 C12 1.398(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(3) . ?
C1 C15 1.368(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(2) . ?
C4 C16 1.403(2) . ?
C5 C6 1.386(2) . ?
C5 C17 1.388(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(3) . ?
C8 H8 0.9300 . ?
C8 C19 1.377(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(3) . ?
C9 C14 1.392(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(2) . ?
C11 C12 1.399(2) . ?
C12 C13 1.405(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.393(2) . ?
C17 C18 1.498(2) . ?
C17 C19 1.398(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 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
O1 S1 C11 109.98(9) . . ?
O1 S1 C16 110.37(9) . . ?
O2 S1 O1 115.87(10) . . ?
O2 S1 C11 109.34(9) . . ?
O2 S1 C16 108.14(9) . . ?
C11 S1 C16 102.26(7) . . ?
C4 N1 C5 118.46(12) . . ?
C4 N1 C12 123.64(12) . . ?
C12 N1 C5 117.90(12) . . ?
C2 C1 H1 120.7 . . ?
C15 C1 H1 120.7 . . ?
C15 C1 C2 118.57(17) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.60(18) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.10(16) . . ?
C4 C3 H3 119.5 . . ?
N1 C4 C3 121.23(13) . . ?
N1 C4 C16 122.33(14) . . ?
C16 C4 C3 116.44(14) . . ?
C6 C5 N1 119.41(15) . . ?
C6 C5 C17 121.86(14) . . ?
C17 C5 N1 118.73(14) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.50(17) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.73(17) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C19 120.10(16) . . ?
C19 C8 H8 120.0 . . ?
C10 C9 H9 120.5 . . ?
C10 C9 C14 119.00(17) . . ?
C14 C9 H9 120.5 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.50(17) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 S1 116.58(12) . . ?
C10 C11 C12 121.48(15) . . ?
C12 C11 S1 121.65(12) . . ?
N1 C12 C11 123.03(14) . . ?
N1 C12 C13 120.22(13) . . ?
C11 C12 C13 116.74(15) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.15(16) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.08(18) . . ?
C13 C14 H14 119.5 . . ?
C1 C15 H15 119.7 . . ?
C1 C15 C16 120.62(17) . . ?
C16 C15 H15 119.7 . . ?
C4 C16 S1 121.66(12) . . ?
C15 C16 S1 116.18(12) . . ?
C15 C16 C4 121.61(16) . . ?
C5 C17 C18 121.64(14) . . ?
C5 C17 C19 116.96(15) . . ?
C19 C17 C18 121.36(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 C17 121.83(17) . . ?
C8 C19 H19 119.1 . . ?
C17 C19 H19 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C11 C12 N1 -4.8(2) . . . . ?
S1 C11 C12 C13 174.47(13) . . . . ?
O1 S1 C11 C10 -48.67(17) . . . . ?
O1 S1 C11 C12 137.42(15) . . . . ?
O1 S1 C16 C4 -140.72(14) . . . . ?
O1 S1 C16 C15 47.66(17) . . . . ?
O2 S1 C11 C10 79.62(16) . . . . ?
O2 S1 C11 C12 -94.28(15) . . . . ?
O2 S1 C16 C4 91.58(15) . . . . ?
O2 S1 C16 C15 -80.03(16) . . . . ?
N1 C4 C16 S1 12.1(2) . . . . ?
N1 C4 C16 C15 -176.70(16) . . . . ?
N1 C5 C6 C7 179.41(15) . . . . ?
N1 C5 C17 C18 3.4(2) . . . . ?
N1 C5 C17 C19 -178.87(14) . . . . ?
N1 C12 C13 C14 176.99(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C15 C16 S1 169.86(16) . . . . ?
C1 C15 C16 C4 -1.8(3) . . . . ?
C2 C1 C15 C16 -0.7(3) . . . . ?
C2 C3 C4 N1 177.84(17) . . . . ?
C2 C3 C4 C16 -1.8(3) . . . . ?
C3 C4 C16 S1 -168.23(13) . . . . ?
C3 C4 C16 C15 2.9(2) . . . . ?
C4 N1 C5 C6 -80.95(19) . . . . ?
C4 N1 C5 C17 99.64(17) . . . . ?
C4 N1 C12 C11 -12.8(2) . . . . ?
C4 N1 C12 C13 167.88(15) . . . . ?
C5 N1 C4 C3 9.6(2) . . . . ?
C5 N1 C4 C16 -170.83(15) . . . . ?
C5 N1 C12 C11 166.89(15) . . . . ?
C5 N1 C12 C13 -12.4(2) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C5 C17 C19 C8 -1.0(3) . . . . ?
C6 C5 C17 C18 -176.01(16) . . . . ?
C6 C5 C17 C19 1.7(2) . . . . ?
C6 C7 C8 C19 0.9(3) . . . . ?
C7 C8 C19 C17 -0.4(3) . . . . ?
C9 C10 C11 S1 -172.77(17) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C9 C14 C13 0.2(3) . . . . ?
C10 C11 C12 N1 -178.44(16) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 S1 C16 C4 -23.74(16) . . . . ?
C11 S1 C16 C15 164.64(14) . . . . ?
C11 C12 C13 C14 -2.3(3) . . . . ?
C12 N1 C4 C3 -170.71(15) . . . . ?
C12 N1 C4 C16 8.9(2) . . . . ?
C12 N1 C5 C6 99.31(18) . . . . ?
C12 N1 C5 C17 -80.10(18) . . . . ?
C12 C13 C14 C9 1.8(3) . . . . ?
C14 C9 C10 C11 -1.7(3) . . . . ?
C15 C1 C2 C3 1.8(3) . . . . ?
C16 S1 C11 C10 -165.93(15) . . . . ?
C16 S1 C11 C12 20.17(16) . . . . ?
C17 C5 C6 C7 -1.2(3) . . . . ?
C18 C17 C19 C8 176.80(17) . . . . ?

_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_maoht190508_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2041004'
loop_
_audit_author_name
_audit_author_address
maoht
;Northeast Normal University
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O2 S'
_chemical_formula_sum            'C20 H17 N O2 S'
_chemical_formula_weight         335.40
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.1938(10)
_cell_length_b                   8.0950(5)
_cell_length_c                   25.4630(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.695(3)
_cell_angle_gamma                90
_cell_volume                     3299.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      50.000
_cell_measurement_theta_min      1.953
_shelx_estimated_absorpt_T_max   0.54
_shelx_estimated_absorpt_T_min   0.21
_exptl_absorpt_coefficient_mu    1.833
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15533
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.256
_diffrn_reflns_theta_min         3.512
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2953
_reflns_number_total             3223
_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       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -1.093
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0663
_refine_ls_restrained_S_all      1.212
_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)+(0.1051P)²+1.4113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1704
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.32389(3) 1.04030(6) 0.44445(2) 0.0391(2) Uani 1 1 d . . . . .
O1 O 0.36840(12) 1.0861(2) 0.49537(7) 0.0629(5) Uani 1 1 d . . . . .
O2 O 0.30551(12) 1.1715(2) 0.40657(8) 0.0607(5) Uani 1 1 d . . . . .
N1 N 0.24489(10) 0.7548(2) 0.37762(6) 0.0345(4) Uani 1 1 d . . . . .
C1 C 0.15581(17) 0.2062(3) 0.29962(11) 0.0551(6) Uani 1 1 d . . . . .
H1A H 0.104723 0.165882 0.279675 0.083 Uiso 1 1 calc GR . . . .
H1B H 0.159489 0.171472 0.335950 0.083 Uiso 1 1 calc GR . . . .
H1C H 0.202407 0.162671 0.284807 0.083 Uiso 1 1 calc GR . . . .
C2 C 0.15709(13) 0.3920(3) 0.29714(8) 0.0385(5) Uani 1 1 d . . . . .
C3 C 0.19827(12) 0.4845(3) 0.33946(8) 0.0361(4) Uani 1 1 d . . . . .
H3 H 0.223049 0.432195 0.370396 0.043 Uiso 1 1 calc R . . . .
C4 C 0.20189(11) 0.6546(2) 0.33495(7) 0.0319(4) Uani 1 1 d . . . . .
C5 C 0.33201(12) 0.7660(2) 0.38338(7) 0.0324(4) Uani 1 1 d . . . . .
C6 C 0.37667(12) 0.8842(2) 0.41637(7) 0.0344(4) Uani 1 1 d . . . . .
C7 C 0.46385(13) 0.8862(3) 0.42516(8) 0.0432(5) Uani 1 1 d . . . . .
H7 H 0.491992 0.965007 0.447682 0.052 Uiso 1 1 calc R . . . .
C8 C 0.50829(14) 0.7728(3) 0.40085(10) 0.0494(6) Uani 1 1 d . . . . .
H8 H 0.566375 0.772883 0.407047 0.059 Uiso 1 1 calc R . . . .
C9 C 0.11907(13) 0.4750(3) 0.25210(8) 0.0412(5) Uani 1 1 d . . . . .
H9 H 0.090891 0.414008 0.224018 0.049 Uiso 1 1 calc R . . . .
C10 C 0.12163(12) 0.6448(3) 0.24756(7) 0.0389(5) Uani 1 1 d . . . . .
C11 C 0.16456(12) 0.7351(3) 0.28954(8) 0.0357(4) Uani 1 1 d . . . . .
H11 H 0.168184 0.849386 0.287088 0.043 Uiso 1 1 calc R . . . .
C12 C 0.46487(14) 0.6577(3) 0.36676(10) 0.0487(5) Uani 1 1 d . . . . .
H12 H 0.494492 0.581523 0.349580 0.058 Uiso 1 1 calc R . . . .
C13 C 0.37880(13) 0.6542(3) 0.35789(8) 0.0409(5) Uani 1 1 d . . . . .
H13 H 0.351350 0.576418 0.334639 0.049 Uiso 1 1 calc R . . . .
C14 C 0.23159(13) 0.9410(2) 0.45158(7) 0.0342(4) Uani 1 1 d . . . . .
C15 C 0.18718(15) 0.9964(3) 0.49121(8) 0.0441(5) Uani 1 1 d . . . . .
H15 H 0.211074 1.073591 0.515993 0.053 Uiso 1 1 calc R . . . .
C16 C 0.10889(17) 0.9374(3) 0.49365(10) 0.0518(6) Uani 1 1 d . . . . .
H16 H 0.079333 0.973638 0.520067 0.062 Uiso 1 1 calc R . . . .
C17 C 0.07402(15) 0.8231(3) 0.45634(10) 0.0491(5) Uani 1 1 d . . . . .
H17 H 0.020026 0.785422 0.457346 0.059 Uiso 1 1 calc R . . . .
C18 C 0.11748(13) 0.7637(3) 0.41765(9) 0.0414(5) Uani 1 1 d . . . . .
H18 H 0.092877 0.685768 0.393348 0.050 Uiso 1 1 calc R . . . .
C19 C 0.19840(12) 0.8201(2) 0.41484(7) 0.0319(4) Uani 1 1 d . . . . .
C20 C 0.07853(18) 0.7300(4) 0.19843(10) 0.0631(7) Uani 1 1 d . . . . .
H20A H 0.118107 0.750454 0.174658 0.095 Uiso 1 1 calc GR . . . .
H20B H 0.055599 0.832997 0.208115 0.095 Uiso 1 1 calc GR . . . .
H20C H 0.034405 0.660938 0.181160 0.095 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4338(16) . ?
S1 O2 1.4351(18) . ?
S1 C6 1.739(2) . ?
S1 C14 1.730(2) . ?
N1 C4 1.447(2) . ?
N1 C5 1.399(2) . ?
N1 C19 1.400(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.506(3) . ?
C2 C3 1.396(3) . ?
C2 C9 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C4 C11 1.384(3) . ?
C5 C6 1.400(3) . ?
C5 C13 1.401(3) . ?
C6 C7 1.396(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(3) . ?
C8 H8 0.9300 . ?
C8 C12 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(3) . ?
C10 C11 1.391(3) . ?
C10 C20 1.505(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.399(3) . ?
C14 C19 1.404(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.400(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 116.18(12) . . ?
O1 S1 C6 110.41(10) . . ?
O1 S1 C14 110.45(11) . . ?
O2 S1 C6 109.05(11) . . ?
O2 S1 C14 108.63(10) . . ?
C14 S1 C6 101.06(9) . . ?
C5 N1 C4 118.56(15) . . ?
C5 N1 C19 122.78(15) . . ?
C19 N1 C4 118.23(15) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.7(2) . . ?
C9 C2 C1 120.7(2) . . ?
C9 C2 C3 118.56(19) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.38(18) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 N1 121.13(17) . . ?
C11 C4 N1 117.61(17) . . ?
C11 C4 C3 121.27(17) . . ?
N1 C5 C6 121.88(17) . . ?
N1 C5 C13 121.13(17) . . ?
C6 C5 C13 116.94(18) . . ?
C5 C6 S1 120.13(15) . . ?
C7 C6 S1 118.30(15) . . ?
C7 C6 C5 121.47(19) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.50(19) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C12 118.7(2) . . ?
C12 C8 H8 120.6 . . ?
C2 C9 H9 118.8 . . ?
C10 C9 C2 122.36(18) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C11 118.46(19) . . ?
C9 C10 C20 120.7(2) . . ?
C11 C10 C20 120.9(2) . . ?
C4 C11 C10 119.94(19) . . ?
C4 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C8 C12 H12 119.3 . . ?
C13 C12 C8 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C5 C13 H13 119.5 . . ?
C12 C13 C5 121.01(19) . . ?
C12 C13 H13 119.5 . . ?
C15 C14 S1 118.27(16) . . ?
C15 C14 C19 121.2(2) . . ?
C19 C14 S1 120.24(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
N1 C19 C14 121.59(17) . . ?
C18 C19 N1 120.96(17) . . ?
C18 C19 C14 117.43(18) . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
S1 C6 C7 C8 -175.37(18) . . . . ?
S1 C14 C15 C16 171.03(19) . . . . ?
S1 C14 C19 N1 11.7(3) . . . . ?
S1 C14 C19 C18 -169.95(15) . . . . ?
O1 S1 C6 C5 148.04(17) . . . . ?
O1 S1 C6 C7 -35.6(2) . . . . ?
O1 S1 C14 C15 37.1(2) . . . . ?
O1 S1 C14 C19 -149.40(16) . . . . ?
O2 S1 C6 C5 -83.18(18) . . . . ?
O2 S1 C6 C7 93.21(18) . . . . ?
O2 S1 C14 C15 -91.35(19) . . . . ?
O2 S1 C14 C19 82.11(18) . . . . ?
N1 C4 C11 C10 -179.30(17) . . . . ?
N1 C5 C6 S1 -8.9(3) . . . . ?
N1 C5 C6 C7 174.85(18) . . . . ?
N1 C5 C13 C12 -175.1(2) . . . . ?
C1 C2 C3 C4 176.8(2) . . . . ?
C1 C2 C9 C10 -177.5(2) . . . . ?
C2 C3 C4 N1 -179.19(17) . . . . ?
C2 C3 C4 C11 0.8(3) . . . . ?
C2 C9 C10 C11 0.6(3) . . . . ?
C2 C9 C10 C20 -179.1(2) . . . . ?
C3 C2 C9 C10 0.9(3) . . . . ?
C3 C4 C11 C10 0.7(3) . . . . ?
C4 N1 C5 C6 167.14(18) . . . . ?
C4 N1 C5 C13 -15.5(3) . . . . ?
C4 N1 C19 C14 -168.60(18) . . . . ?
C4 N1 C19 C18 13.1(3) . . . . ?
C5 N1 C4 C3 79.5(2) . . . . ?
C5 N1 C4 C11 -100.5(2) . . . . ?
C5 N1 C19 C14 19.0(3) . . . . ?
C5 N1 C19 C18 -159.24(19) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 S1 C14 C15 154.02(17) . . . . ?
C6 S1 C14 C19 -32.52(18) . . . . ?
C6 C5 C13 C12 2.4(3) . . . . ?
C6 C7 C8 C12 0.9(4) . . . . ?
C7 C8 C12 C13 -1.1(4) . . . . ?
C8 C12 C13 C5 -0.5(4) . . . . ?
C9 C2 C3 C4 -1.6(3) . . . . ?
C9 C10 C11 C4 -1.4(3) . . . . ?
C13 C5 C6 S1 173.70(15) . . . . ?
C13 C5 C6 C7 -2.6(3) . . . . ?
C14 S1 C6 C5 31.14(18) . . . . ?
C14 S1 C6 C7 -152.47(16) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C15 C14 C19 N1 -175.02(19) . . . . ?
C15 C14 C19 C18 3.3(3) . . . . ?
C15 C16 C17 C18 1.9(4) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 N1 176.6(2) . . . . ?
C17 C18 C19 C14 -1.7(3) . . . . ?
C19 N1 C4 C3 -93.2(2) . . . . ?
C19 N1 C4 C11 86.8(2) . . . . ?
C19 N1 C5 C6 -20.5(3) . . . . ?
C19 N1 C5 C13 156.8(2) . . . . ?
C19 C14 C15 C16 -2.4(3) . . . . ?
C20 C10 C11 C4 178.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
