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

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

data_0324dzb_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2bks90
_database_code_depnum_ccdc_archive 'CCDC 2162042'
loop_
_audit_author_name
_audit_author_address
'Xiao-Hu Xu'
;Wuhan Institute of Technology School of Chemistry and Environmental Engineering
China
;
_audit_update_record             
;
2022-03-25 deposited with the CCDC.	2022-10-13 downloaded from the CCDC.
;
_audit_creation_date             2022-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 N2 O S'
_chemical_formula_sum            'C22 H16 N2 O S'
_chemical_formula_weight         356.43
_chemical_absolute_configuration ?
_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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   5.8239(14)
_cell_length_b                   15.770(4)
_cell_length_c                   9.954(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.110(6)
_cell_angle_gamma                90
_cell_volume                     905.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.89
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10105
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.437
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.735
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                2037
_reflns_number_total             2760
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.174
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.076
_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)+(0.0330P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0886
_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:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
;
_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
S001 S 0.5735(2) 0.30766(8) 0.27648(13) 0.0478(4) Uani 1 1 d . . . . .
O002 O 0.4477(6) 0.4887(2) 0.2095(3) 0.0556(10) Uani 1 1 d . . . . .
N003 N 0.6918(7) 0.1625(3) 0.4257(4) 0.0479(11) Uani 1 1 d . . . . .
N004 N 0.5000(7) 0.2726(2) 0.5199(4) 0.0454(10) Uani 1 1 d . . . . .
C005 C 0.7967(8) 0.1285(3) 0.3175(5) 0.0410(12) Uani 1 1 d . . . . .
C006 C 0.3648(8) 0.4642(3) 0.3091(5) 0.0429(12) Uani 1 1 d . . . . .
C007 C 0.6033(8) 0.2364(3) 0.4152(4) 0.0403(12) Uani 1 1 d . . . . .
C008 C 0.2150(8) 0.5199(3) 0.3816(5) 0.0402(12) Uani 1 1 d . . . . .
C009 C 0.7120(9) 0.0533(3) 0.2580(5) 0.0508(13) Uani 1 1 d . . . . .
H009 H 0.582906 0.027733 0.286143 0.061 Uiso 1 1 calc R . . . .
C00A C 0.4899(9) 0.2279(3) 0.6448(4) 0.0412(12) Uani 1 1 d . . . . .
C00B C 0.0233(9) 0.4901(3) 0.4343(5) 0.0504(14) Uani 1 1 d . . . . .
H00B H -0.021375 0.433686 0.421481 0.060 Uiso 1 1 calc R . . . .
C00C C 1.0986(9) 0.1263(4) 0.1762(5) 0.0569(14) Uani 1 1 d . . . . .
H00C H 1.230041 0.150708 0.149234 0.068 Uiso 1 1 calc R . . . .
C00D C 0.2736(8) 0.6049(3) 0.3961(5) 0.0469(13) Uani 1 1 d . . . . .
H00D H 0.398030 0.626093 0.357247 0.056 Uiso 1 1 calc R . . . .
C00E C 0.6625(10) 0.1877(4) 0.8654(6) 0.0636(16) Uani 1 1 d . . . . .
H00E H 0.787639 0.189253 0.934624 0.076 Uiso 1 1 calc R . . . .
C00F C 0.8177(11) 0.0159(4) 0.1574(6) 0.0629(16) Uani 1 1 d . . . . .
H00F H 0.757905 -0.033952 0.116685 0.076 Uiso 1 1 calc R . . . .
C00G C 0.4704(10) 0.1419(3) 0.8821(5) 0.0571(15) Uani 1 1 d . . . . .
H00G H 0.464459 0.112668 0.962734 0.069 Uiso 1 1 calc R . . . .
C00H C 0.6733(9) 0.2320(3) 0.7462(5) 0.0558(14) Uani 1 1 d . . . . .
H00H H 0.803651 0.263983 0.735591 0.067 Uiso 1 1 calc R . . . .
C00I C 0.9915(8) 0.1646(3) 0.2757(5) 0.0492(14) Uani 1 1 d . . . . .
H00I H 1.050788 0.214936 0.314997 0.059 Uiso 1 1 calc R . . . .
C00J C 0.4217(7) 0.3801(3) 0.3655(5) 0.0409(12) Uani 1 1 d . . . . .
C00K C 0.2969(9) 0.1824(4) 0.6613(5) 0.0579(15) Uani 1 1 d . . . . .
H00K H 0.171552 0.180736 0.592234 0.069 Uiso 1 1 calc R . . . .
C00L C 1.0115(11) 0.0524(4) 0.1171(5) 0.0634(16) Uani 1 1 d . . . . .
H00L H 1.083365 0.026916 0.049831 0.076 Uiso 1 1 calc R . . . .
C00M C 0.4043(8) 0.3507(3) 0.4907(5) 0.0438(13) Uani 1 1 d . . . . .
H00M H 0.332260 0.381385 0.552842 0.053 Uiso 1 1 calc R . . . .
C00N C 0.1496(10) 0.6575(4) 0.4669(6) 0.0611(15) Uani 1 1 d . . . . .
H00N H 0.190680 0.714364 0.477280 0.073 Uiso 1 1 calc R . . . .
C00O C 0.2876(10) 0.1387(4) 0.7812(6) 0.0634(15) Uani 1 1 d . . . . .
H00O H 0.156456 0.107341 0.792523 0.076 Uiso 1 1 calc R . . . .
C00P C -0.0358(10) 0.6270(4) 0.5232(6) 0.0663(17) Uani 1 1 d . . . . .
H00P H -0.117439 0.662892 0.573556 0.080 Uiso 1 1 calc R . . . .
C00Q C -0.1017(9) 0.5434(4) 0.5055(5) 0.0623(16) Uani 1 1 d . . . . .
H00Q H -0.229993 0.523248 0.541631 0.075 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
S001 C007 1.769(5) . ?
S001 C00J 1.759(4) . ?
O002 C006 1.225(6) . ?
N003 C005 1.416(6) . ?
N003 C007 1.273(6) . ?
N004 C007 1.397(5) . ?
N004 C00A 1.437(5) . ?
N004 C00M 1.367(6) . ?
C005 C009 1.385(6) . ?
C005 C00I 1.384(6) . ?
C006 C008 1.494(7) . ?
C006 C00J 1.459(6) . ?
C008 C00B 1.381(7) . ?
C008 C00D 1.387(6) . ?
C009 C00F 1.379(7) . ?
C00A C00H 1.364(6) . ?
C00A C00K 1.363(7) . ?
C00B C00Q 1.373(7) . ?
C00C C00I 1.382(7) . ?
C00C C00L 1.369(8) . ?
C00D C00N 1.360(7) . ?
C00E C00G 1.361(8) . ?
C00E C00H 1.386(7) . ?
C00F C00L 1.376(8) . ?
C00G C00O 1.358(7) . ?
C00J C00M 1.348(6) . ?
C00K C00O 1.386(7) . ?
C00N C00P 1.372(8) . ?
C00P C00Q 1.376(7) . ?

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
C00J S001 C007 91.2(2) . . ?
C007 N003 C005 119.8(4) . . ?
C007 N004 C00A 121.3(4) . . ?
C00M N004 C007 114.5(4) . . ?
C00M N004 C00A 124.1(4) . . ?
C009 C005 N003 118.9(5) . . ?
C00I C005 N003 122.2(4) . . ?
C00I C005 C009 118.8(5) . . ?
O002 C006 C008 122.0(4) . . ?
O002 C006 C00J 120.3(4) . . ?
C00J C006 C008 117.7(4) . . ?
N003 C007 S001 129.8(4) . . ?
N003 C007 N004 121.6(4) . . ?
N004 C007 S001 108.5(3) . . ?
C00B C008 C006 122.8(4) . . ?
C00B C008 C00D 119.4(4) . . ?
C00D C008 C006 117.8(4) . . ?
C00F C009 C005 120.5(5) . . ?
C00H C00A N004 119.6(5) . . ?
C00K C00A N004 119.8(4) . . ?
C00K C00A C00H 120.6(5) . . ?
C00Q C00B C008 120.2(5) . . ?
C00L C00C C00I 120.2(5) . . ?
C00N C00D C008 120.2(5) . . ?
C00G C00E C00H 120.6(5) . . ?
C00L C00F C009 120.1(5) . . ?
C00O C00G C00E 120.1(5) . . ?
C00A C00H C00E 119.0(5) . . ?
C00C C00I C005 120.5(5) . . ?
C006 C00J S001 120.0(4) . . ?
C00M C00J S001 110.6(3) . . ?
C00M C00J C006 128.7(4) . . ?
C00A C00K C00O 119.9(5) . . ?
C00C C00L C00F 120.0(5) . . ?
C00J C00M N004 115.2(4) . . ?
C00D C00N C00P 120.3(5) . . ?
C00G C00O C00K 119.8(5) . . ?
C00N C00P C00Q 120.3(5) . . ?
C00B C00Q C00P 119.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
