# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20200709QYL6881
_database_code_depnum_ccdc_archive 'CCDC 2129607'
loop_
_audit_author_name
_audit_author_address
'Ya-Jing Chen'
;Zhengzhou University
China
;
_audit_update_record             
;
2021-12-18 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N3 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         391.48

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   8.6347(16)
_cell_length_b                   6.1566(11)
_cell_length_c                   35.983(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.175(7)
_cell_angle_gamma                90
_cell_volume                     1905.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.4659
_cell_measurement_theta_max      65.4978
_cell_measurement_temperature    276.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    1.698
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.81

_exptl_special_details           
;
;

_diffrn_ambient_temperature      276.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'cu k\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11438
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         65.49
_diffrn_reflns_theta_full        65.49
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42

_refine_special_details          
;
;

_reflns_number_total             3183
_reflns_number_gt                2900
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1107
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_number_reflns         3183
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+1.0503P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.419
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.28224(5) 0.65923(7) 0.42659(2) 0.02726(17) Uani d . . . 1 . .
O O1 0.15818(15) 0.5484(2) 0.44198(4) 0.0343(3) Uani d . . . 1 . .
O O3 0.29930(16) 0.8894(2) 0.43101(4) 0.0356(4) Uani d . . . 1 . .
N N3 0.4241(2) 0.8879(3) 0.35891(5) 0.0360(4) Uani d . . . 1 . .
H H21 0.402(3) 0.949(5) 0.3804(8) 0.055(8) Uiso d . . . 1 . .
N N1 0.25400(17) 0.6131(2) 0.38099(4) 0.0251(4) Uani d . . . 1 . .
N N2 0.35296(18) 0.5670(2) 0.32592(4) 0.0280(4) Uani d . . . 1 . .
C C1 0.8864(3) 0.2066(4) 0.47675(6) 0.0432(5) Uani d . . . 1 . .
H H4 0.874083 0.123055 0.49882 0.065 Uiso calc U . R 1 . .
H H3 0.968287 0.310776 0.481895 0.065 Uiso calc U . R 1 . .
H H1 0.912303 0.111488 0.457095 0.065 Uiso calc U . R 1 . .
C C2 0.7370(2) 0.3232(3) 0.46493(5) 0.0308(4) Uani d . . . 1 . .
C C3 0.5944(2) 0.2244(3) 0.46867(5) 0.0339(5) Uani d . . . 1 . .
H H20 0.592392 0.086071 0.478989 0.041 Uiso calc U . R 1 . .
C C4 0.4554(2) 0.3271(3) 0.45740(6) 0.0309(4) Uani d . . . 1 . .
H H5 0.36108 0.258651 0.460091 0.037 Uiso calc U . R 1 . .
C C5 0.4588(2) 0.5332(3) 0.44207(5) 0.0262(4) Uani d . . . 1 . .
C C6 0.3522(2) 0.7075(3) 0.35560(5) 0.0261(4) Uani d . . . 1 . .
C C7 0.4217(2) 0.6007(3) 0.29224(5) 0.0303(4) Uani d . . . 1 . .
C C8 0.5082(2) 0.7860(4) 0.28521(6) 0.0393(5) Uani d . . . 1 . .
H H19 0.518902 0.897629 0.30266 0.047 Uiso calc U . R 1 . .
C C9 0.5776(3) 0.8023(4) 0.25230(7) 0.0484(6) Uani d . . . 1 . .
H H18 0.634535 0.92624 0.2478 0.058 Uiso calc U . R 1 . .
C C10 0.5648(3) 0.6405(4) 0.22602(6) 0.0466(6) Uani d . . . 1 . .
H H2 0.614457 0.652361 0.204223 0.056 Uiso calc U . R 1 . .
C C11 0.6000(2) 0.6373(3) 0.43841(5) 0.0304(4) Uani d . . . 1 . .
H H6 0.601927 0.776503 0.428433 0.036 Uiso calc U . R 1 . .
C C12 0.7375(2) 0.5308(3) 0.44983(5) 0.0330(5) Uani d . . . 1 . .
H H7 0.831889 0.59964 0.447331 0.04 Uiso calc U . R 1 . .
C C13 0.2567(2) 0.3756(3) 0.33003(5) 0.0280(4) Uani d . . . 1 . .
H H8 0.316499 0.243925 0.327411 0.034 Uiso calc U . R 1 . .
H H15 0.168391 0.375001 0.311355 0.034 Uiso calc U . R 1 . .
C C14 0.2025(2) 0.3914(3) 0.36926(5) 0.0240(4) Uani d . . . 1 . .
H H9 0.25708 0.283246 0.385583 0.029 Uiso calc U . R 1 . .
C C15 0.0286(2) 0.3583(3) 0.36868(5) 0.0234(4) Uani d . . . 1 . .
C C16 -0.0286(2) 0.1564(3) 0.37781(5) 0.0297(4) Uani d . . . 1 . .
H H14 0.039427 0.047799 0.386919 0.036 Uiso calc U . R 1 . .
C C17 -0.1881(2) 0.1164(3) 0.37331(6) 0.0355(5) Uani d . . . 1 . .
H H10 -0.225941 -0.019801 0.37907 0.043 Uiso calc U . R 1 . .
C C18 -0.2895(2) 0.2767(4) 0.36045(6) 0.0367(5) Uani d . . . 1 . .
H H13 -0.395714 0.248849 0.357432 0.044 Uiso calc U . R 1 . .
C C19 -0.2337(2) 0.4797(3) 0.35197(6) 0.0355(5) Uani d . . . 1 . .
H H11 -0.302532 0.589166 0.343655 0.043 Uiso calc U . R 1 . .
C C20 -0.0750(2) 0.5197(3) 0.35589(5) 0.0297(4) Uani d . . . 1 . .
H H12 -0.037688 0.655749 0.349887 0.036 Uiso calc U . R 1 . .
C C21 0.4767(3) 0.4592(4) 0.23259(7) 0.0497(6) Uani d . . . 1 . .
H H17 0.465464 0.349637 0.214762 0.06 Uiso calc U . R 1 . .
C C22 0.4052(3) 0.4384(4) 0.26509(6) 0.0407(5) Uani d . . . 1 . .
H H16 0.34574 0.315925 0.268963 0.049 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4238(15) ?
S1 O3 . 1.4322(14) ?
S1 N1 . 1.6614(15) ?
S1 C5 . 1.7561(18) ?
N3 C6 . 1.272(3) ?
N3 H21 . 0.90(3) ?
N1 C6 . 1.426(2) ?
N1 C14 . 1.484(2) ?
N2 C6 . 1.375(2) ?
N2 C7 . 1.412(3) ?
N2 C13 . 1.457(2) ?
C1 C2 . 1.504(3) ?
C1 H4 . 0.96 ?
C1 H3 . 0.96 ?
C1 H1 . 0.96 ?
C2 C12 . 1.389(3) ?
C2 C3 . 1.391(3) ?
C3 C4 . 1.385(3) ?
C3 H20 . 0.93 ?
C4 C5 . 1.385(3) ?
C4 H5 . 0.93 ?
C5 C11 . 1.394(3) ?
C7 C22 . 1.395(3) ?
C7 C8 . 1.399(3) ?
C8 C9 . 1.378(3) ?
C8 H19 . 0.93 ?
C9 C10 . 1.371(4) ?
C9 H18 . 0.93 ?
C10 C21 . 1.383(4) ?
C10 H2 . 0.93 ?
C11 C12 . 1.386(3) ?
C11 H6 . 0.93 ?
C12 H7 . 0.93 ?
C13 C14 . 1.530(3) ?
C13 H8 . 0.97 ?
C13 H15 . 0.97 ?
C14 C15 . 1.514(2) ?
C14 H9 . 0.98 ?
C15 C20 . 1.387(3) ?
C15 C16 . 1.388(3) ?
C16 C17 . 1.393(3) ?
C16 H14 . 0.93 ?
C17 C18 . 1.372(3) ?
C17 H10 . 0.93 ?
C18 C19 . 1.383(3) ?
C18 H13 . 0.93 ?
C19 C20 . 1.387(3) ?
C19 H11 . 0.93 ?
C20 H12 . 0.93 ?
C21 C22 . 1.377(3) ?
C21 H17 . 0.93 ?
C22 H16 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O3 . . 120.29(9) ?
O1 S1 N1 . . 104.70(8) ?
O3 S1 N1 . . 106.48(8) ?
O1 S1 C5 . . 109.09(9) ?
O3 S1 C5 . . 108.91(8) ?
N1 S1 C5 . . 106.48(8) ?
C6 N3 H21 . . 107.6(18) ?
C6 N1 C14 . . 111.91(15) ?
C6 N1 S1 . . 121.35(12) ?
C14 N1 S1 . . 116.84(12) ?
C6 N2 C7 . . 127.29(16) ?
C6 N2 C13 . . 112.80(15) ?
C7 N2 C13 . . 119.59(15) ?
C2 C1 H4 . . 109.5 ?
C2 C1 H3 . . 109.5 ?
H4 C1 H3 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H4 C1 H1 . . 109.5 ?
H3 C1 H1 . . 109.5 ?
C12 C2 C3 . . 118.30(18) ?
C12 C2 C1 . . 121.2(2) ?
C3 C2 C1 . . 120.54(19) ?
C4 C3 C2 . . 121.58(19) ?
C4 C3 H20 . . 119.2 ?
C2 C3 H20 . . 119.2 ?
C3 C4 C5 . . 119.08(19) ?
C3 C4 H5 . . 120.5 ?
C5 C4 H5 . . 120.5 ?
C4 C5 C11 . . 120.59(18) ?
C4 C5 S1 . . 118.82(15) ?
C11 C5 S1 . . 120.58(15) ?
N3 C6 N2 . . 125.84(19) ?
N3 C6 N1 . . 127.56(19) ?
N2 C6 N1 . . 106.60(15) ?
C22 C7 C8 . . 118.6(2) ?
C22 C7 N2 . . 118.13(18) ?
C8 C7 N2 . . 123.22(19) ?
C9 C8 C7 . . 119.7(2) ?
C9 C8 H19 . . 120.2 ?
C7 C8 H19 . . 120.2 ?
C10 C9 C8 . . 121.7(2) ?
C10 C9 H18 . . 119.1 ?
C8 C9 H18 . . 119.1 ?
C9 C10 C21 . . 118.7(2) ?
C9 C10 H2 . . 120.7 ?
C21 C10 H2 . . 120.7 ?
C12 C11 C5 . . 119.20(19) ?
C12 C11 H6 . . 120.4 ?
C5 C11 H6 . . 120.4 ?
C11 C12 C2 . . 121.24(19) ?
C11 C12 H7 . . 119.4 ?
C2 C12 H7 . . 119.4 ?
N2 C13 C14 . . 105.47(14) ?
N2 C13 H8 . . 110.6 ?
C14 C13 H8 . . 110.6 ?
N2 C13 H15 . . 110.6 ?
C14 C13 H15 . . 110.6 ?
H8 C13 H15 . . 108.8 ?
N1 C14 C15 . . 113.51(14) ?
N1 C14 C13 . . 102.26(14) ?
C15 C14 C13 . . 111.36(14) ?
N1 C14 H9 . . 109.8 ?
C15 C14 H9 . . 109.8 ?
C13 C14 H9 . . 109.8 ?
C20 C15 C16 . . 119.18(17) ?
C20 C15 C14 . . 121.13(17) ?
C16 C15 C14 . . 119.41(16) ?
C15 C16 C17 . . 119.98(18) ?
C15 C16 H14 . . 120.0 ?
C17 C16 H14 . . 120.0 ?
C18 C17 C16 . . 120.39(19) ?
C18 C17 H10 . . 119.8 ?
C16 C17 H10 . . 119.8 ?
C17 C18 C19 . . 120.02(18) ?
C17 C18 H13 . . 120.0 ?
C19 C18 H13 . . 120.0 ?
C18 C19 C20 . . 119.88(18) ?
C18 C19 H11 . . 120.1 ?
C20 C19 H11 . . 120.1 ?
C15 C20 C19 . . 120.54(18) ?
C15 C20 H12 . . 119.7 ?
C19 C20 H12 . . 119.7 ?
C22 C21 C10 . . 121.1(2) ?
C22 C21 H17 . . 119.5 ?
C10 C21 H17 . . 119.5 ?
C21 C22 C7 . . 120.2(2) ?
C21 C22 H16 . . 119.9 ?
C7 C22 H16 . . 119.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N1 C6 . . . . 177.06(14) ?
O3 S1 N1 C6 . . . . 48.64(15) ?
C5 S1 N1 C6 . . . . -67.46(15) ?
O1 S1 N1 C14 . . . . -40.02(14) ?
O3 S1 N1 C14 . . . . -168.44(12) ?
C5 S1 N1 C14 . . . . 75.46(14) ?
C12 C2 C3 C4 . . . . 0.7(3) ?
C1 C2 C3 C4 . . . . -178.90(19) ?
C2 C3 C4 C5 . . . . -0.1(3) ?
C3 C4 C5 C11 . . . . -0.8(3) ?
C3 C4 C5 S1 . . . . 178.15(15) ?
O1 S1 C5 C4 . . . . 16.11(18) ?
O3 S1 C5 C4 . . . . 149.17(15) ?
N1 S1 C5 C4 . . . . -96.38(16) ?
O1 S1 C5 C11 . . . . -164.99(15) ?
O3 S1 C5 C11 . . . . -31.93(19) ?
N1 S1 C5 C11 . . . . 82.53(17) ?
C7 N2 C6 N3 . . . . -5.5(3) ?
C13 N2 C6 N3 . . . . -178.88(18) ?
C7 N2 C6 N1 . . . . 173.43(16) ?
C13 N2 C6 N1 . . . . 0.07(19) ?
C14 N1 C6 N3 . . . . -174.66(17) ?
S1 N1 C6 N3 . . . . -30.1(2) ?
C14 N1 C6 N2 . . . . 6.41(18) ?
S1 N1 C6 N2 . . . . 150.97(12) ?
C6 N2 C7 C22 . . . . -178.24(17) ?
C13 N2 C7 C22 . . . . -5.3(3) ?
C6 N2 C7 C8 . . . . 3.3(3) ?
C13 N2 C7 C8 . . . . 176.24(17) ?
C22 C7 C8 C9 . . . . -1.4(3) ?
N2 C7 C8 C9 . . . . 177.05(18) ?
C7 C8 C9 C10 . . . . -0.3(3) ?
C8 C9 C10 C21 . . . . 1.6(3) ?
C4 C5 C11 C12 . . . . 0.9(3) ?
S1 C5 C11 C12 . . . . -177.98(15) ?
C5 C11 C12 C2 . . . . -0.2(3) ?
C3 C2 C12 C11 . . . . -0.5(3) ?
C1 C2 C12 C11 . . . . 179.05(19) ?
C6 N2 C13 C14 . . . . -6.1(2) ?
C7 N2 C13 C14 . . . . 179.98(15) ?
C6 N1 C14 C15 . . . . -129.77(16) ?
S1 N1 C14 C15 . . . . 83.94(16) ?
C6 N1 C14 C13 . . . . -9.70(17) ?
S1 N1 C14 C13 . . . . -155.99(12) ?
N2 C13 C14 N1 . . . . 9.08(17) ?
N2 C13 C14 C15 . . . . 130.63(15) ?
N1 C14 C15 C20 . . . . 39.8(2) ?
C13 C14 C15 C20 . . . . -74.9(2) ?
N1 C14 C15 C16 . . . . -146.22(17) ?
C13 C14 C15 C16 . . . . 99.0(2) ?
C20 C15 C16 C17 . . . . 1.4(3) ?
C14 C15 C16 C17 . . . . -172.70(17) ?
C15 C16 C17 C18 . . . . -1.0(3) ?
C16 C17 C18 C19 . . . . -0.2(3) ?
C17 C18 C19 C20 . . . . 1.1(3) ?
C16 C15 C20 C19 . . . . -0.5(3) ?
C14 C15 C20 C19 . . . . 173.49(18) ?
C18 C19 C20 C15 . . . . -0.8(3) ?
C9 C10 C21 C22 . . . . -1.2(3) ?
C10 C21 C22 C7 . . . . -0.5(3) ?
C8 C7 C22 C21 . . . . 1.8(3) ?
N2 C7 C22 C21 . . . . -176.78(19) ?

####################################################################### 
# 
# 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_mo_20210521WCC_87_0m
_database_code_depnum_ccdc_archive 'CCDC 2129609'
loop_
_audit_author_name
_audit_author_address
'Ya-Jing Chen'
;Zhengzhou University
China
;
_audit_update_record             
;
2021-12-18 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 Cl N3 O2 S'
_chemical_formula_weight         439.94

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'
Cl Cl 0.1484 0.1585 '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'
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/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                   13.4605(8)
_cell_length_b                   8.4799(5)
_cell_length_c                   19.7332(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.521(2)
_cell_angle_gamma                90
_cell_volume                     2198.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    306(2)
_cell_measurement_reflns_used    5299
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      24.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.293
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      306(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38730
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.624
_diffrn_reflns_theta_max         26.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4540
_reflns_number_gt                2603
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0726P)²+1.1262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4540
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1715
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001

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
C2 C 0.8785(3) 0.0276(4) 0.64741(18) 0.0548(9) Uani 1 1 d . . . . .
H2 H 0.900314 -0.014370 0.609575 0.066 Uiso 1 1 calc R U . . .
C1 C 0.9484(2) 0.0892(4) 0.70225(18) 0.0506(8) Uani 1 1 d . . . . .
C3 C 0.7759(3) 0.0274(4) 0.64806(17) 0.0518(8) Uani 1 1 d . . . . .
H3 H 0.729252 -0.014348 0.610587 0.062 Uiso 1 1 calc R U . . .
C4 C 0.7420(2) 0.0891(3) 0.70414(16) 0.0451(7) Uani 1 1 d . . . . .
C5 C 0.8143(3) 0.1538(4) 0.75858(18) 0.0588(9) Uani 1 1 d . . . . .
H5 H 0.793374 0.198935 0.796109 0.071 Uiso 1 1 calc R U . . .
C6 C 0.9162(3) 0.1516(4) 0.7574(2) 0.0602(9) Uani 1 1 d . . . . .
H6 H 0.963512 0.193133 0.794614 0.072 Uiso 1 1 calc R U . . .
C7 C 0.4956(2) 0.1358(4) 0.75781(17) 0.0523(8) Uani 1 1 d . . . . .
H7 H 0.456649 0.233918 0.755994 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6080(3) 0.1739(5) 0.76500(19) 0.0686(11) Uani 1 1 d . . . . .
H8A H 0.617976 0.286715 0.761657 0.082 Uiso 1 1 calc R U . . .
H8B H 0.647310 0.137240 0.809326 0.082 Uiso 1 1 calc R U . . .
C9 C 0.5570(2) 0.0294(4) 0.66174(17) 0.0469(8) Uani 1 1 d . . . . .
C10 C 0.4727(3) 0.0301(4) 0.81481(19) 0.0651(10) Uani 1 1 d . . . . .
H10A H 0.403489 -0.008930 0.800974 0.078 Uiso 1 1 calc R U . . .
H10B H 0.518134 -0.060000 0.820698 0.078 Uiso 1 1 calc R U . . .
C11 C 0.4849(3) 0.1152(4) 0.88254(18) 0.0526(8) Uani 1 1 d . . . . .
C12 C 0.4100(3) 0.2161(5) 0.8940(2) 0.0654(10) Uani 1 1 d . . . . .
H12 H 0.351597 0.229807 0.859388 0.079 Uiso 1 1 calc R U . . .
C13 C 0.4197(3) 0.2969(5) 0.9554(2) 0.0794(12) Uani 1 1 d . . . . .
H13 H 0.367535 0.362520 0.962463 0.095 Uiso 1 1 calc R U . . .
C14 C 0.5809(3) 0.1816(5) 0.9960(2) 0.0756(11) Uani 1 1 d . . . . .
H14 H 0.639249 0.169068 1.030736 0.091 Uiso 1 1 calc R U . . .
C15 C 0.5710(3) 0.1000(5) 0.9349(2) 0.0660(10) Uani 1 1 d . . . . .
H15 H 0.623065 0.033172 0.928669 0.079 Uiso 1 1 calc R U . . .
C16 C 0.3568(2) 0.2434(4) 0.58888(19) 0.0556(9) Uani 1 1 d . . . . .
C17 C 0.3453(3) 0.3926(5) 0.6160(2) 0.0723(11) Uani 1 1 d . . . . .
H17 H 0.338081 0.403400 0.661545 0.087 Uiso 1 1 calc R U . . .
C18 C 0.3447(3) 0.5232(5) 0.5749(3) 0.0813(13) Uani 1 1 d . . . . .
H18 H 0.337554 0.622420 0.593338 0.098 Uiso 1 1 calc R U . . .
C19 C 0.3544(3) 0.5111(5) 0.5071(2) 0.0766(12) Uani 1 1 d . . . . .
C20 C 0.3663(3) 0.3620(5) 0.4808(2) 0.0766(11) Uani 1 1 d . . . . .
H20 H 0.373307 0.351461 0.435160 0.092 Uiso 1 1 calc R U . . .
C21 C 0.3679(3) 0.2295(5) 0.5214(2) 0.0664(10) Uani 1 1 d . . . . .
H21 H 0.376461 0.130524 0.503169 0.080 Uiso 1 1 calc R U . . .
C22 C 0.3484(4) 0.6539(6) 0.4610(3) 0.1113(17) Uani 1 1 d . . . . .
H22A H 0.375553 0.628516 0.421216 0.167 Uiso 1 1 calc R U . . .
H22B H 0.387286 0.738273 0.486399 0.167 Uiso 1 1 calc R U . . .
H22C H 0.278740 0.686118 0.446173 0.167 Uiso 1 1 calc R U . . .
C23 C 0.5060(4) 0.2810(5) 1.0060(2) 0.0844(13) Uani 1 1 d . . . . .
H23 H 0.513523 0.337661 1.047159 0.101 Uiso 1 1 calc R U . . .
N1 N 0.47042(19) 0.0570(3) 0.68921(14) 0.0536(7) Uani 1 1 d . . . . .
N2 N 0.63869(19) 0.0924(3) 0.70838(13) 0.0469(6) Uani 1 1 d . . . . .
N3 N 0.5623(2) -0.0412(4) 0.60625(16) 0.0628(9) Uani 1 1 d . . . . .
H24 H 0.509(3) -0.075(5) 0.586(2) 0.094 Uiso 1 1 d . U . . .
Cl1 Cl 1.07693(6) 0.08767(11) 0.70194(5) 0.0656(3) Uani 1 1 d . . . . .
S1 S 0.35502(6) 0.07496(11) 0.63941(5) 0.0609(3) Uani 1 1 d . . . . .
O1 O 0.33912(19) -0.0583(3) 0.59441(14) 0.0748(8) Uani 1 1 d . . . . .
O2 O 0.29037(18) 0.1030(4) 0.68673(15) 0.0830(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
C2 C1 1.374(5) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9300 . ?
C1 C6 1.363(5) . ?
C1 Cl1 1.732(3) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(5) . ?
C4 N2 1.411(4) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.481(4) . ?
C7 C10 1.521(5) . ?
C7 C8 1.524(4) . ?
C7 H7 0.9800 . ?
C8 N2 1.448(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N3 1.263(4) . ?
C9 N2 1.379(4) . ?
C9 N1 1.408(4) . ?
C10 C11 1.496(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.378(5) . ?
C11 C15 1.382(5) . ?
C12 C13 1.373(5) . ?
C12 H12 0.9300 . ?
C13 C23 1.364(6) . ?
C13 H13 0.9300 . ?
C14 C23 1.362(6) . ?
C14 C15 1.370(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.377(5) . ?
C16 C17 1.395(5) . ?
C16 S1 1.745(4) . ?
C17 C18 1.371(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(6) . ?
C19 C22 1.506(6) . ?
C20 C21 1.377(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
N1 S1 1.655(3) . ?
N3 H24 0.80(4) . ?
S1 O1 1.425(3) . ?
S1 O2 1.428(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C6 C1 C2 119.7(3) . . ?
C6 C1 Cl1 119.8(3) . . ?
C2 C1 Cl1 120.6(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 N2 123.6(3) . . ?
C5 C4 N2 118.6(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C10 111.6(3) . . ?
N1 C7 C8 101.9(2) . . ?
C10 C7 C8 114.4(3) . . ?
N1 C7 H7 109.6 . . ?
C10 C7 H7 109.6 . . ?
C8 C7 H7 109.6 . . ?
N2 C8 C7 105.7(3) . . ?
N2 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
N2 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
N3 C9 N2 125.1(3) . . ?
N3 C9 N1 128.3(3) . . ?
N2 C9 N1 106.6(3) . . ?
C11 C10 C7 112.1(3) . . ?
C11 C10 H10A 109.2 . . ?
C7 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C7 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C15 117.4(3) . . ?
C12 C11 C10 120.2(3) . . ?
C15 C11 C10 122.3(3) . . ?
C13 C12 C11 121.4(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C23 C13 C12 120.0(4) . . ?
C23 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C23 C14 C15 120.4(4) . . ?
C23 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C11 121.1(4) . . ?
C14 C15 H15 119.5 . . ?
C11 C15 H15 119.5 . . ?
C21 C16 C17 119.5(4) . . ?
C21 C16 S1 120.0(3) . . ?
C17 C16 S1 120.5(3) . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 121.7(4) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C20 118.3(4) . . ?
C18 C19 C22 121.5(4) . . ?
C20 C19 C22 120.2(4) . . ?
C21 C20 C19 120.9(4) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 120.1(4) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C23 C14 119.6(4) . . ?
C13 C23 H23 120.2 . . ?
C14 C23 H23 120.2 . . ?
C9 N1 C7 112.5(2) . . ?
C9 N1 S1 122.4(2) . . ?
C7 N1 S1 120.0(2) . . ?
C9 N2 C4 127.3(3) . . ?
C9 N2 C8 112.4(2) . . ?
C4 N2 C8 120.3(3) . . ?
C9 N3 H24 112(3) . . ?
O1 S1 O2 120.64(17) . . ?
O1 S1 N1 106.97(15) . . ?
O2 S1 N1 104.70(15) . . ?
O1 S1 C16 108.18(17) . . ?
O2 S1 C16 108.84(17) . . ?
N1 S1 C16 106.69(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
C3 C2 C1 C6 -0.5(5) . . . . ?
C3 C2 C1 Cl1 179.3(2) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C2 C3 C4 N2 -179.8(3) . . . . ?
C3 C4 C5 C6 -2.1(5) . . . . ?
N2 C4 C5 C6 179.1(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
Cl1 C1 C6 C5 -180.0(3) . . . . ?
C4 C5 C6 C1 1.5(6) . . . . ?
N1 C7 C8 N2 -9.5(4) . . . . ?
C10 C7 C8 N2 111.1(3) . . . . ?
N1 C7 C10 C11 -172.6(3) . . . . ?
C8 C7 C10 C11 72.4(4) . . . . ?
C7 C10 C11 C12 78.4(4) . . . . ?
C7 C10 C11 C15 -100.0(4) . . . . ?
C15 C11 C12 C13 -0.9(5) . . . . ?
C10 C11 C12 C13 -179.3(4) . . . . ?
C11 C12 C13 C23 1.6(6) . . . . ?
C23 C14 C15 C11 -0.5(6) . . . . ?
C12 C11 C15 C14 0.4(5) . . . . ?
C10 C11 C15 C14 178.8(3) . . . . ?
C21 C16 C17 C18 0.3(6) . . . . ?
S1 C16 C17 C18 -178.6(3) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
C17 C18 C19 C20 -0.9(6) . . . . ?
C17 C18 C19 C22 176.9(4) . . . . ?
C18 C19 C20 C21 0.3(6) . . . . ?
C22 C19 C20 C21 -177.5(4) . . . . ?
C19 C20 C21 C16 0.5(6) . . . . ?
C17 C16 C21 C20 -0.8(5) . . . . ?
S1 C16 C21 C20 178.1(3) . . . . ?
C12 C13 C23 C14 -1.7(7) . . . . ?
C15 C14 C23 C13 1.2(7) . . . . ?
N3 C9 N1 C7 176.5(4) . . . . ?
N2 C9 N1 C7 -2.2(4) . . . . ?
N3 C9 N1 S1 -28.8(5) . . . . ?
N2 C9 N1 S1 152.4(2) . . . . ?
C10 C7 N1 C9 -115.0(3) . . . . ?
C8 C7 N1 C9 7.4(4) . . . . ?
C10 C7 N1 S1 89.6(3) . . . . ?
C8 C7 N1 S1 -147.9(3) . . . . ?
N3 C9 N2 C4 -0.9(5) . . . . ?
N1 C9 N2 C4 178.0(3) . . . . ?
N3 C9 N2 C8 176.7(4) . . . . ?
N1 C9 N2 C8 -4.5(4) . . . . ?
C3 C4 N2 C9 4.1(5) . . . . ?
C5 C4 N2 C9 -177.2(3) . . . . ?
C3 C4 N2 C8 -173.3(3) . . . . ?
C5 C4 N2 C8 5.5(5) . . . . ?
C7 C8 N2 C9 9.1(4) . . . . ?
C7 C8 N2 C4 -173.1(3) . . . . ?
C9 N1 S1 O1 51.5(3) . . . . ?
C7 N1 S1 O1 -155.7(3) . . . . ?
C9 N1 S1 O2 -179.4(3) . . . . ?
C7 N1 S1 O2 -26.6(3) . . . . ?
C9 N1 S1 C16 -64.1(3) . . . . ?
C7 N1 S1 C16 88.7(3) . . . . ?
C21 C16 S1 O1 -15.2(3) . . . . ?
C17 C16 S1 O1 163.7(3) . . . . ?
C21 C16 S1 O2 -148.0(3) . . . . ?
C17 C16 S1 O2 31.0(3) . . . . ?
C21 C16 S1 N1 99.6(3) . . . . ?
C17 C16 S1 N1 -81.5(3) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_20201015wcc
_database_code_depnum_ccdc_archive 'CCDC 2129608'
loop_
_audit_author_name
_audit_author_address
'Ya-Jing Chen'
;Zhengzhou University
China
;
_audit_update_record             
;
2021-12-18 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Br N3 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         470.38

_chemical_melting_point          ?

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

_cell_length_a                   8.4289(7)
_cell_length_b                   8.9127(7)
_cell_length_c                   14.3601(13)
_cell_angle_alpha                102.292(3)
_cell_angle_beta                 92.181(4)
_cell_angle_gamma                93.615(3)
_cell_volume                     1050.50(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.4245
_cell_measurement_theta_max      28.3118
_cell_measurement_temperature    301.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    2.079
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.77

_exptl_special_details           
;
;

_diffrn_ambient_temperature      301.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            37904
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             5229
_reflns_number_gt                4249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0941
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_number_reflns         5229
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.3951P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.577
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1109)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.74988(3) 1.20397(3) 0.99610(2) 0.08007(12) Uani d . . . 1 . .
S S1 0.71389(6) 0.29790(5) 0.50410(3) 0.04466(12) Uani d . . . 1 . .
O O2 0.58633(18) 0.20170(19) 0.44989(10) 0.0597(4) Uani d . . . 1 . .
O O3 0.81803(18) 0.38941(18) 0.45849(10) 0.0562(4) Uani d . . . 1 . .
N N3 0.8515(2) 0.5970(2) 0.65486(13) 0.0508(4) Uani d . . . 1 . .
H H20 0.896(3) 0.558(3) 0.6049(17) 0.054(6) Uiso d . . . 1 . .
N N1 0.61051(17) 0.57717(17) 0.72935(11) 0.0396(3) Uani d . . . 1 . .
N N2 0.62571(18) 0.41974(18) 0.58567(11) 0.0423(3) Uani d . . . 1 . .
C C1 0.7009(3) 1.0060(2) 0.91609(15) 0.0532(5) Uani d . . . 1 . .
C C2 0.5589(3) 0.9725(3) 0.8650(2) 0.0685(7) Uani d . . . 1 . .
H H16 0.483444 1.045273 0.870937 0.082 Uiso calc U . R 1 . .
C C3 0.5273(2) 0.8299(2) 0.80405(18) 0.0599(6) Uani d . . . 1 . .
H H17 0.430158 0.807052 0.769344 0.072 Uiso calc U . R 1 . .
C C4 0.6388(2) 0.7215(2) 0.79447(12) 0.0393(4) Uani d . . . 1 . .
C C5 0.7129(2) 0.53608(19) 0.65527(12) 0.0387(3) Uani d . . . 1 . .
C C6 0.8294(2) 0.1898(2) 0.56511(13) 0.0427(4) Uani d . . . 1 . .
C C7 0.7565(2) 0.0724(2) 0.60230(16) 0.0530(5) Uani d . . . 1 . .
H H10 0.647487 0.047566 0.592147 0.064 Uiso calc U . R 1 . .
C C8 0.8484(3) -0.0063(2) 0.65439(17) 0.0582(5) Uani d . . . 1 . .
H H15 0.799953 -0.083927 0.679994 0.07 Uiso calc U . R 1 . .
C C9 1.0117(2) 0.0277(2) 0.66954(15) 0.0499(4) Uani d . . . 1 . .
C C10 1.1112(3) -0.0557(3) 0.7284(2) 0.0712(6) Uani d . . . 1 . .
H H14 1.218843 -0.053127 0.708922 0.107 Uiso calc U . R 1 . .
H H1 1.068951 -0.160657 0.719143 0.107 Uiso calc U . R 1 . .
H H13 1.109205 -0.006423 0.794588 0.107 Uiso calc U . R 1 . .
C C11 0.8124(3) 0.8976(3) 0.90896(16) 0.0586(5) Uani d . . . 1 . .
H H19 0.908478 0.920151 0.944798 0.07 Uiso calc U . R 1 . .
C C12 0.7804(3) 0.7558(2) 0.84849(15) 0.0539(5) Uani d . . . 1 . .
H H18 0.855019 0.682464 0.843996 0.065 Uiso calc U . R 1 . .
C C13 0.4473(2) 0.5115(2) 0.70077(13) 0.0405(4) Uani d . . . 1 . .
H H2 0.38938 0.583095 0.671477 0.049 Uiso calc U . R 1 . .
C C14 0.3550(2) 0.4714(2) 0.78112(13) 0.0399(4) Uani d . . . 1 . .
C C15 0.1923(2) 0.4876(2) 0.78105(15) 0.0493(4) Uani d . . . 1 . .
H H3 0.143705 0.531585 0.735193 0.059 Uiso calc U . R 1 . .
C C16 0.1022(3) 0.4385(3) 0.84911(18) 0.0610(6) Uani d . . . 1 . .
H H4 -0.007277 0.44704 0.847701 0.073 Uiso calc U . R 1 . .
C C17 0.1739(3) 0.3775(3) 0.91854(17) 0.0618(6) Uani d . . . 1 . .
H H5 0.113118 0.34521 0.964332 0.074 Uiso calc U . R 1 . .
C C18 0.3358(3) 0.3639(3) 0.92044(16) 0.0589(5) Uani d . . . 1 . .
H H6 0.384392 0.323717 0.968018 0.071 Uiso calc U . R 1 . .
C C19 0.4260(2) 0.4100(2) 0.85192(15) 0.0505(4) Uani d . . . 1 . .
H H7 0.535093 0.399706 0.853221 0.061 Uiso calc U . R 1 . .
C C20 0.4774(2) 0.3697(2) 0.62460(14) 0.0477(4) Uani d . . . 1 . .
H H8 0.491212 0.280949 0.652343 0.057 Uiso calc U . R 1 . .
H H9 0.39119 0.345221 0.575917 0.057 Uiso calc U . R 1 . .
C C21 1.0806(3) 0.1403(2) 0.62855(18) 0.0585(5) Uani d . . . 1 . .
H H12 1.190404 0.16161 0.635742 0.07 Uiso calc U . R 1 . .
C C22 0.9915(2) 0.2222(2) 0.57712(17) 0.0545(5) Uani d . . . 1 . .
H H11 1.040482 0.298775 0.550798 0.065 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.901(2) ?
S1 O2 . 1.4258(15) ?
S1 O3 . 1.4303(14) ?
S1 N2 . 1.6523(16) ?
S1 C6 . 1.748(2) ?
N3 C5 . 1.258(2) ?
N3 H20 . 0.84(2) ?
N1 C5 . 1.398(2) ?
N1 C4 . 1.421(2) ?
N1 C13 . 1.469(2) ?
N2 C5 . 1.421(2) ?
N2 C20 . 1.471(2) ?
C1 C2 . 1.362(3) ?
C1 C11 . 1.381(3) ?
C2 C3 . 1.385(3) ?
C2 H16 . 0.93 ?
C3 C4 . 1.379(3) ?
C3 H17 . 0.93 ?
C4 C12 . 1.379(3) ?
C6 C22 . 1.375(3) ?
C6 C7 . 1.392(3) ?
C7 C8 . 1.378(3) ?
C7 H10 . 0.93 ?
C8 C9 . 1.390(3) ?
C8 H15 . 0.93 ?
C9 C21 . 1.376(3) ?
C9 C10 . 1.504(3) ?
C10 H14 . 0.96 ?
C10 H1 . 0.96 ?
C10 H13 . 0.96 ?
C11 C12 . 1.376(3) ?
C11 H19 . 0.93 ?
C12 H18 . 0.93 ?
C13 C14 . 1.507(2) ?
C13 C20 . 1.527(3) ?
C13 H2 . 0.98 ?
C14 C19 . 1.387(3) ?
C14 C15 . 1.388(3) ?
C15 C16 . 1.386(3) ?
C15 H3 . 0.93 ?
C16 C17 . 1.372(3) ?
C16 H4 . 0.93 ?
C17 C18 . 1.377(3) ?
C17 H5 . 0.93 ?
C18 C19 . 1.380(3) ?
C18 H6 . 0.93 ?
C19 H7 . 0.93 ?
C20 H8 . 0.97 ?
C20 H9 . 0.97 ?
C21 C22 . 1.379(3) ?
C21 H12 . 0.93 ?
C22 H11 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O3 . . 119.87(9) ?
O2 S1 N2 . . 104.52(9) ?
O3 S1 N2 . . 106.35(9) ?
O2 S1 C6 . . 109.95(9) ?
O3 S1 C6 . . 108.49(9) ?
N2 S1 C6 . . 106.83(8) ?
C5 N3 H20 . . 111.3(16) ?
C5 N1 C4 . . 119.63(14) ?
C5 N1 C13 . . 111.21(14) ?
C4 N1 C13 . . 120.60(14) ?
C5 N2 C20 . . 110.03(14) ?
C5 N2 S1 . . 122.30(12) ?
C20 N2 S1 . . 120.08(12) ?
C2 C1 C11 . . 120.43(19) ?
C2 C1 Br1 . . 120.39(16) ?
C11 C1 Br1 . . 119.16(16) ?
C1 C2 C3 . . 119.8(2) ?
C1 C2 H16 . . 120.1 ?
C3 C2 H16 . . 120.1 ?
C4 C3 C2 . . 120.51(19) ?
C4 C3 H17 . . 119.7 ?
C2 C3 H17 . . 119.7 ?
C12 C4 C3 . . 118.94(18) ?
C12 C4 N1 . . 119.97(16) ?
C3 C4 N1 . . 121.09(17) ?
N3 C5 N1 . . 123.99(17) ?
N3 C5 N2 . . 130.26(17) ?
N1 C5 N2 . . 105.74(14) ?
C22 C6 C7 . . 120.33(18) ?
C22 C6 S1 . . 119.87(15) ?
C7 C6 S1 . . 119.80(15) ?
C8 C7 C6 . . 118.97(19) ?
C8 C7 H10 . . 120.5 ?
C6 C7 H10 . . 120.5 ?
C7 C8 C9 . . 121.51(19) ?
C7 C8 H15 . . 119.2 ?
C9 C8 H15 . . 119.2 ?
C21 C9 C8 . . 117.91(19) ?
C21 C9 C10 . . 120.6(2) ?
C8 C9 C10 . . 121.4(2) ?
C9 C10 H14 . . 109.5 ?
C9 C10 H1 . . 109.5 ?
H14 C10 H1 . . 109.5 ?
C9 C10 H13 . . 109.5 ?
H14 C10 H13 . . 109.5 ?
H1 C10 H13 . . 109.5 ?
C12 C11 C1 . . 119.6(2) ?
C12 C11 H19 . . 120.2 ?
C1 C11 H19 . . 120.2 ?
C11 C12 C4 . . 120.71(19) ?
C11 C12 H18 . . 119.6 ?
C4 C12 H18 . . 119.6 ?
N1 C13 C14 . . 114.18(14) ?
N1 C13 C20 . . 101.27(14) ?
C14 C13 C20 . . 112.51(15) ?
N1 C13 H2 . . 109.5 ?
C14 C13 H2 . . 109.5 ?
C20 C13 H2 . . 109.5 ?
C19 C14 C15 . . 118.95(18) ?
C19 C14 C13 . . 121.94(16) ?
C15 C14 C13 . . 118.99(16) ?
C16 C15 C14 . . 120.22(19) ?
C16 C15 H3 . . 119.9 ?
C14 C15 H3 . . 119.9 ?
C17 C16 C15 . . 120.2(2) ?
C17 C16 H4 . . 119.9 ?
C15 C16 H4 . . 119.9 ?
C16 C17 C18 . . 120.0(2) ?
C16 C17 H5 . . 120.0 ?
C18 C17 H5 . . 120.0 ?
C17 C18 C19 . . 120.1(2) ?
C17 C18 H6 . . 119.9 ?
C19 C18 H6 . . 119.9 ?
C18 C19 C14 . . 120.45(19) ?
C18 C19 H7 . . 119.8 ?
C14 C19 H7 . . 119.8 ?
N2 C20 C13 . . 102.08(14) ?
N2 C20 H8 . . 111.4 ?
C13 C20 H8 . . 111.4 ?
N2 C20 H9 . . 111.4 ?
C13 C20 H9 . . 111.4 ?
H8 C20 H9 . . 109.2 ?
C9 C21 C22 . . 121.81(19) ?
C9 C21 H12 . . 119.1 ?
C22 C21 H12 . . 119.1 ?
C6 C22 C21 . . 119.38(18) ?
C6 C22 H11 . . 120.3 ?
C21 C22 H11 . . 120.3 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S1 N2 C5 . . . . 179.70(14) ?
O3 S1 N2 C5 . . . . -52.56(15) ?
C6 S1 N2 C5 . . . . 63.18(15) ?
O2 S1 N2 C20 . . . . 33.14(16) ?
O3 S1 N2 C20 . . . . 160.89(14) ?
C6 S1 N2 C20 . . . . -83.38(15) ?
C11 C1 C2 C3 . . . . -1.2(4) ?
Br1 C1 C2 C3 . . . . 177.4(2) ?
C1 C2 C3 C4 . . . . -0.2(4) ?
C2 C3 C4 C12 . . . . 1.8(4) ?
C2 C3 C4 N1 . . . . -177.4(2) ?
C5 N1 C4 C12 . . . . -59.7(2) ?
C13 N1 C4 C12 . . . . 155.20(18) ?
C5 N1 C4 C3 . . . . 119.5(2) ?
C13 N1 C4 C3 . . . . -25.6(3) ?
C4 N1 C5 N3 . . . . 19.5(3) ?
C13 N1 C5 N3 . . . . 167.57(17) ?
C4 N1 C5 N2 . . . . -159.46(14) ?
C13 N1 C5 N2 . . . . -11.35(18) ?
C20 N2 C5 N3 . . . . 171.4(2) ?
S1 N2 C5 N3 . . . . 21.9(3) ?
C20 N2 C5 N1 . . . . -9.80(19) ?
S1 N2 C5 N1 . . . . -159.30(12) ?
O2 S1 C6 C22 . . . . 144.28(17) ?
O3 S1 C6 C22 . . . . 11.43(19) ?
N2 S1 C6 C22 . . . . -102.86(17) ?
O2 S1 C6 C7 . . . . -36.49(18) ?
O3 S1 C6 C7 . . . . -169.34(16) ?
N2 S1 C6 C7 . . . . 76.37(17) ?
C22 C6 C7 C8 . . . . 2.5(3) ?
S1 C6 C7 C8 . . . . -176.69(17) ?
C6 C7 C8 C9 . . . . -0.7(3) ?
C7 C8 C9 C21 . . . . -1.8(3) ?
C7 C8 C9 C10 . . . . 178.5(2) ?
C2 C1 C11 C12 . . . . 1.1(4) ?
Br1 C1 C11 C12 . . . . -177.59(18) ?
C1 C11 C12 C4 . . . . 0.5(4) ?
C3 C4 C12 C11 . . . . -1.9(3) ?
N1 C4 C12 C11 . . . . 177.3(2) ?
C5 N1 C13 C14 . . . . 147.65(15) ?
C4 N1 C13 C14 . . . . -64.6(2) ?
C5 N1 C13 C20 . . . . 26.49(18) ?
C4 N1 C13 C20 . . . . 174.24(15) ?
N1 C13 C14 C19 . . . . -37.9(2) ?
C20 C13 C14 C19 . . . . 76.8(2) ?
N1 C13 C14 C15 . . . . 146.13(17) ?
C20 C13 C14 C15 . . . . -99.2(2) ?
C19 C14 C15 C16 . . . . -2.0(3) ?
C13 C14 C15 C16 . . . . 174.13(18) ?
C14 C15 C16 C17 . . . . 1.8(3) ?
C15 C16 C17 C18 . . . . -0.4(4) ?
C16 C17 C18 C19 . . . . -0.8(4) ?
C17 C18 C19 C14 . . . . 0.6(3) ?
C15 C14 C19 C18 . . . . 0.8(3) ?
C13 C14 C19 C18 . . . . -175.18(19) ?
C5 N2 C20 C13 . . . . 25.54(19) ?
S1 N2 C20 C13 . . . . 175.81(12) ?
N1 C13 C20 N2 . . . . -29.91(17) ?
C14 C13 C20 N2 . . . . -152.24(15) ?
C8 C9 C21 C22 . . . . 2.6(3) ?
C10 C9 C21 C22 . . . . -177.7(2) ?
C7 C6 C22 C21 . . . . -1.7(3) ?
S1 C6 C22 C21 . . . . 177.48(17) ?
C9 C21 C22 C6 . . . . -0.9(4) ?

