# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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. 
# 
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data_201909220
_database_code_depnum_ccdc_archive 'CCDC 1954608'
loop_
_audit_author_name
_audit_author_address
'Zhen-Hua Wang'
;Chengdu University
China
;
_audit_update_record             
;
2019-09-19 deposited with the CCDC.	2023-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 Br N O2 S'
_chemical_formula_sum            'C22 H18 Br N O2 S'
_chemical_formula_weight         440.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O4b
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'
Br Br -0.6763 1.2805 '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                   13.8433(6)
_cell_length_b                   14.8254(6)
_cell_length_c                   9.4672(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.436(4)
_cell_angle_gamma                90
_cell_volume                     1942.93(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1716
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9830
_cell_measurement_theta_min      4.3490
_shelx_estimated_absorpt_T_max   0.713
_shelx_estimated_absorpt_T_min   0.623
_exptl_absorpt_coefficient_mu    4.023
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7440
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.370
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  31.00   1.00    1.00    --  -33.50  57.00 150.00   35
  2  ω   -105.00 -34.00   1.00    1.00    --  -33.50 178.00 150.00   71
  3  ω    -52.00 -14.00   1.00    1.00    --  -33.50  57.00 150.00   38
  4  ω     60.00  87.00   1.00    1.00    --   36.54 178.00  60.00   27
  5  ω      9.00  37.00   1.00    1.00    --   36.54  77.00  60.00   28
  6  ω     65.00  92.00   1.00    1.00    --   36.54  77.00-150.00   27
  7  ω      9.00  51.00   1.00    1.00    --   36.54  77.00-150.00   42
  8  ω     57.00  96.00   1.00    1.00    --   36.54 178.00-120.00   39
  9  ω     47.00 104.00   1.00    1.00    --   36.54  77.00  60.00   57
 10  ω     64.00  90.00   1.00    1.00    --   36.54 178.00 120.00   26
 11  ω     51.00  77.00   1.00    1.00    --   36.54 -99.00 -90.00   26
 12  ω     99.00 125.00   1.00    1.00    --  108.00  61.00 -90.00   26
 13  ω     45.00  80.00   1.00    1.00    --  108.00 -77.00 -90.00   35
 14  ω    128.00 155.00   1.00    1.00    --  108.00  61.00 -90.00   27
 15  ω     80.00 177.00   1.00    1.00    --  108.00  77.00 -30.00   97
 16  ω    100.00 126.00   1.00    1.00    --  108.00 -45.00  30.00   26
 17  ω     77.00 103.00   1.00    1.00    --  108.00 -94.00  90.00   26
 18  ω     39.00 104.00   1.00    1.00    --  108.00 -94.00 -30.00   65
 19  ω     67.00 111.00   1.00    1.00    --  108.00 -61.00 -30.00   44
 20  ω     84.00 137.00   1.00    1.00    --  108.00  30.00  90.00   53
 21  ω    100.00 177.00   1.00    1.00    --  108.00 111.00-120.00   77
 22  ω     67.00 126.00   1.00    1.00    --  108.00 -61.00 150.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0127015000
_diffrn_orient_matrix_UB_12      0.0971395000
_diffrn_orient_matrix_UB_13      -0.0543339000
_diffrn_orient_matrix_UB_21      0.1068216000
_diffrn_orient_matrix_UB_22      -0.0198336000
_diffrn_orient_matrix_UB_23      -0.0324831000
_diffrn_orient_matrix_UB_31      -0.0286331000
_diffrn_orient_matrix_UB_32      -0.0308623000
_diffrn_orient_matrix_UB_33      -0.1499957000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2578
_reflns_number_total             3462
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.038
_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)+(0.0678P)²+0.1271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1389
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C7(H7), C15(H15), C14(H14), C12(H12), C11(H11),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Fitted hexagon refined as free rotating group:
 C15(C14,C13,C12,C11,C10)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.16079(4) 0.74730(3) 0.73341(6) 0.0696(2) Uani 1 1 d . . . . .
C1 C 0.2921(3) 0.4996(3) 0.7855(4) 0.0514(10) Uani 1 1 d . . . . .
H1 H 0.3109 0.4631 0.8606 0.062 Uiso 1 1 calc R . . . .
C2 C 0.2449(3) 0.5793(3) 0.8131(4) 0.0534(10) Uani 1 1 d . . . . .
H2 H 0.2307 0.5963 0.9052 0.064 Uiso 1 1 calc R . . . .
C3 C 0.2192(3) 0.6333(3) 0.7000(4) 0.0487(10) Uani 1 1 d . . . . .
C4 C 0.2377(3) 0.6098(2) 0.5631(4) 0.0453(9) Uani 1 1 d . . . . .
H4 H 0.2195 0.6474 0.4889 0.054 Uiso 1 1 calc R . . . .
C5 C 0.2841(3) 0.5288(2) 0.5373(4) 0.0383(8) Uani 1 1 d . . . . .
C6 C 0.3125(3) 0.4720(2) 0.6480(4) 0.0401(8) Uani 1 1 d . . . . .
C7 C 0.3624(3) 0.3878(2) 0.6162(4) 0.0413(8) Uani 1 1 d . . . . .
H7 H 0.3675 0.3437 0.6857 0.050 Uiso 1 1 calc R . . . .
C8 C 0.4010(3) 0.3726(2) 0.4892(4) 0.0386(8) Uani 1 1 d . . . . .
C9 C 0.3929(3) 0.4473(2) 0.3806(4) 0.0411(8) Uani 1 1 d . . . . .
H9A H 0.4488 0.4864 0.3895 0.049 Uiso 1 1 calc R . . . .
H9B H 0.3939 0.4209 0.2869 0.049 Uiso 1 1 calc R . . . .
C15 C 0.09127(19) 0.37772(15) 0.4544(3) 0.0575(11) Uani 1 1 d . . . . .
H15 H 0.0719 0.4327 0.4921 0.069 Uiso 1 1 calc R . . . .
C14 C 0.04999(19) 0.2980(2) 0.5020(3) 0.0686(13) Uani 1 1 d G . . . .
H14 H 0.0029 0.2995 0.5716 0.082 Uiso 1 1 calc R . . . .
C13 C 0.0790(2) 0.21582(15) 0.4457(3) 0.0627(12) Uani 1 1 d G . . . .
C12 C 0.1493(2) 0.21345(13) 0.3417(3) 0.0709(13) Uani 1 1 d G . . . .
H12 H 0.1688 0.1585 0.3040 0.085 Uiso 1 1 calc R . . . .
C11 C 0.19062(19) 0.29322(17) 0.2941(3) 0.0620(12) Uani 1 1 d G . . . .
H11 H 0.2377 0.2916 0.2245 0.074 Uiso 1 1 calc R . . . .
C10 C 0.16159(18) 0.37535(13) 0.3504(3) 0.0402(8) Uani 1 1 d G . . . .
C16 C 0.0320(4) 0.1280(3) 0.4932(6) 0.0914(19) Uani 1 1 d . . . . .
H16A H -0.0242 0.1163 0.4360 0.137 Uiso 1 1 calc GR . . . .
H16B H 0.0135 0.1330 0.5904 0.137 Uiso 1 1 calc GR . . . .
H16C H 0.0771 0.0792 0.4830 0.137 Uiso 1 1 calc GR . . . .
C17 C 0.4534(3) 0.2896(3) 0.4526(4) 0.0417(8) Uani 1 1 d . . . . .
C18 C 0.5274(3) 0.2904(3) 0.3532(5) 0.0557(10) Uani 1 1 d . . . . .
H18 H 0.5429 0.3439 0.3074 0.067 Uiso 1 1 calc R . . . .
C19 C 0.5781(3) 0.2123(4) 0.3222(6) 0.0710(13) Uani 1 1 d . . . . .
H19 H 0.6264 0.2137 0.2544 0.085 Uiso 1 1 calc R . . . .
C20 C 0.5582(3) 0.1339(3) 0.3894(5) 0.0681(13) Uani 1 1 d . . . . .
H20 H 0.5946 0.0825 0.3713 0.082 Uiso 1 1 calc R . . . .
C21 C 0.4839(4) 0.1308(3) 0.4844(5) 0.0672(13) Uani 1 1 d . . . . .
H21 H 0.4692 0.0767 0.5291 0.081 Uiso 1 1 calc R . . . .
C22 C 0.4309(3) 0.2071(3) 0.5144(4) 0.0554(11) Uani 1 1 d . . . . .
H22 H 0.3794 0.2034 0.5766 0.066 Uiso 1 1 calc R . . . .
N1 N 0.3053(2) 0.50159(18) 0.3949(3) 0.0382(7) Uani 1 1 d . . . . .
O1 O 0.1422(2) 0.54564(17) 0.3059(3) 0.0580(7) Uani 1 1 d . . . . .
O2 O 0.2543(2) 0.4586(2) 0.1536(2) 0.0610(8) Uani 1 1 d . . . . .
S1 S 0.21236(7) 0.47555(6) 0.28858(9) 0.0436(2) 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
Br1 C3 1.901(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(5) . ?
C1 C6 1.395(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(5) . ?
C3 C4 1.369(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(5) . ?
C5 C6 1.398(5) . ?
C5 N1 1.440(4) . ?
C6 C7 1.460(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.338(5) . ?
C8 C9 1.514(5) . ?
C8 C17 1.472(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 N1 1.463(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C15 C10 1.3900 . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C13 C12 1.3900 . ?
C13 C16 1.526(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C10 S1 1.746(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.396(5) . ?
C17 C22 1.391(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.354(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.372(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(6) . ?
C22 H22 0.9300 . ?
N1 S1 1.672(3) . ?
O1 S1 1.432(3) . ?
O2 S1 1.430(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
C2 C1 H1 119.0 . . ?
C2 C1 C6 121.9(4) . . ?
C6 C1 H1 119.0 . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.1(4) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 Br1 119.6(3) . . ?
C4 C3 Br1 117.8(3) . . ?
C4 C3 C2 122.5(4) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(4) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 N1 120.4(3) . . ?
C6 C5 N1 118.4(3) . . ?
C1 C6 C5 117.7(3) . . ?
C1 C6 C7 122.9(3) . . ?
C5 C6 C7 119.4(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 117.3(3) . . ?
C7 C8 C17 123.5(3) . . ?
C17 C8 C9 119.1(3) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N1 C9 C8 113.4(3) . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C10 120.0 . . ?
C10 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 C16 120.6(3) . . ?
C12 C13 C16 119.3(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C15 C10 S1 120.12(16) . . ?
C11 C10 C15 120.0 . . ?
C11 C10 S1 119.88(16) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C8 121.1(4) . . ?
C22 C17 C8 121.6(3) . . ?
C22 C17 C18 117.3(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.6(4) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(4) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.9(4) . . ?
C21 C22 H22 119.6 . . ?
C5 N1 C9 114.5(3) . . ?
C5 N1 S1 117.8(2) . . ?
C9 N1 S1 116.9(2) . . ?
N1 S1 C10 107.72(14) . . ?
O1 S1 C10 107.68(16) . . ?
O1 S1 N1 106.42(15) . . ?
O2 S1 C10 108.49(15) . . ?
O2 S1 N1 105.21(16) . . ?
O2 S1 O1 120.68(18) . . ?

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
Br1 C3 C4 C5 177.1(3) . . . . ?
C1 C2 C3 Br1 -176.3(3) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C1 C6 C7 C8 -164.1(4) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
C2 C1 C6 C7 -180.0(4) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C3 C4 C5 N1 -179.8(3) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 C7 -179.2(3) . . . . ?
C4 C5 N1 C9 148.6(3) . . . . ?
C4 C5 N1 S1 -67.9(4) . . . . ?
C5 C6 C7 C8 15.3(5) . . . . ?
C5 N1 S1 C10 -68.9(3) . . . . ?
C5 N1 S1 O1 46.3(3) . . . . ?
C5 N1 S1 O2 175.5(3) . . . . ?
C6 C1 C2 C3 -1.2(6) . . . . ?
C6 C5 N1 C9 -30.8(4) . . . . ?
C6 C5 N1 S1 112.7(3) . . . . ?
C6 C7 C8 C9 1.5(5) . . . . ?
C6 C7 C8 C17 178.9(3) . . . . ?
C7 C8 C9 N1 -31.7(4) . . . . ?
C7 C8 C17 C18 -150.0(4) . . . . ?
C7 C8 C17 C22 30.6(6) . . . . ?
C8 C9 N1 C5 45.9(4) . . . . ?
C8 C9 N1 S1 -97.9(3) . . . . ?
C8 C17 C18 C19 178.3(4) . . . . ?
C8 C17 C22 C21 -176.7(4) . . . . ?
C9 C8 C17 C18 27.3(5) . . . . ?
C9 C8 C17 C22 -152.0(4) . . . . ?
C9 N1 S1 C10 73.7(3) . . . . ?
C9 N1 S1 O1 -171.1(2) . . . . ?
C9 N1 S1 O2 -41.9(3) . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C15 C14 C13 C16 -177.9(3) . . . . ?
C15 C10 S1 N1 86.9(2) . . . . ?
C15 C10 S1 O1 -27.5(2) . . . . ?
C15 C10 S1 O2 -159.71(18) . . . . ?
C14 C15 C10 C11 0.0 . . . . ?
C14 C15 C10 S1 179.1(2) . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C12 C11 C10 C15 0.0 . . . . ?
C12 C11 C10 S1 -179.1(2) . . . . ?
C11 C10 S1 N1 -94.04(19) . . . . ?
C11 C10 S1 O1 151.55(17) . . . . ?
C11 C10 S1 O2 19.4(2) . . . . ?
C10 C15 C14 C13 0.0 . . . . ?
C16 C13 C12 C11 177.9(3) . . . . ?
C17 C8 C9 N1 150.8(3) . . . . ?
C17 C18 C19 C20 -1.2(7) . . . . ?
C18 C17 C22 C21 3.9(6) . . . . ?
C18 C19 C20 C21 3.1(7) . . . . ?
C19 C20 C21 C22 -1.5(8) . . . . ?
C20 C21 C22 C17 -2.1(7) . . . . ?
C22 C17 C18 C19 -2.3(6) . . . . ?
N1 C5 C6 C1 179.6(3) . . . . ?
N1 C5 C6 C7 0.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.015
_oxdiff_exptl_absorpt_empirical_full_min 0.741
####################################################################### 
# 
# 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_20230479_auto
_database_code_depnum_ccdc_archive 'CCDC 2255453'
loop_
_audit_author_name
_audit_author_address
'Zhen-Hua Wang'
;Chengdu University
China
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-07-15 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N O3 S'
_chemical_formula_sum            'C22 H19 N O3 S'
_chemical_formula_weight         377.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N1O1S1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3137(4)
_cell_length_b                   10.2800(9)
_cell_length_c                   11.9158(9)
_cell_angle_alpha                67.229(8)
_cell_angle_beta                 81.908(5)
_cell_angle_gamma                89.234(5)
_cell_volume                     928.71(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3037
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1730
_cell_measurement_theta_min      4.0660
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    1.733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6490
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.068
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 -60.00   93
  2  ω    -56.00  37.00   1.00    1.00    --  -33.50  37.00 120.00   93
  3  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-180.00   73
  4  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00-150.00   87
  5  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00-150.00   75
  6  ω     61.00 110.00   1.00    1.00    --   36.47 178.00  30.00   49
  7  ω     61.00 110.00   1.00    1.00    --   36.47 178.00-150.00   49
  8  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00  30.00   75
  9  ω     40.00 109.00   1.00    1.50    --  108.00-115.00-154.00   69
 10  ω     38.00 107.00   1.00    1.50    --  108.00 -94.00   0.00   69
 11  ω     63.00 178.00   1.00    1.50    --  108.00  15.00 150.00  115
 12  ω     38.00 128.00   1.00    1.50    --  108.00 -45.00  30.00   90
 13  ω     38.00 128.00   1.00    1.50    --  108.00 -45.00 -60.00   90
 14  ω     38.00 107.00   1.00    1.50    --  108.00 -94.00-120.00   69
 15  ω     37.00 134.00   1.00    1.50    --  108.00 -30.00-150.00   97
 16  ω     38.00 107.00   1.00    1.50    --  108.00 -94.00 -90.00   69
 17  ω     44.00  70.00   1.00    1.50    --  108.00 -94.00  60.00   26
 18  ω     63.00  93.00   1.00    1.50    --  108.00  15.00-120.00   30
 19  ω    127.00 156.00   1.00    1.50    --  108.00  15.00-120.00   29
 20  ω     64.00 103.00   1.00    1.50    --  108.00 -94.00  90.00   39
 21  ω    109.00 151.00   1.00    1.50    --  108.00 111.00 -30.00   42
 22  ω     38.00  92.00   1.00    1.50    --  108.00 -94.00 -30.00   54
 23  ω     96.00 178.00   1.00    1.50    --  108.00  45.00  30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0167942000
_diffrn_orient_matrix_UB_12      -0.1179639000
_diffrn_orient_matrix_UB_13      -0.0476923000
_diffrn_orient_matrix_UB_21      0.0032756000
_diffrn_orient_matrix_UB_22      0.1119206000
_diffrn_orient_matrix_UB_23      -0.1315108000
_diffrn_orient_matrix_UB_31      0.1865753000
_diffrn_orient_matrix_UB_32      -0.0052254000
_diffrn_orient_matrix_UB_33      -0.0229187000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2725
_reflns_number_total             3313
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0060(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)²+0.1126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1340
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.46097(6) 0.27278(6) 0.77715(5) 0.0591(2) Uani 1 1 d . . . . .
O1 O 0.40273(19) 0.2734(2) 0.66979(18) 0.0780(5) Uani 1 1 d . . . . .
O2 O 0.37164(19) 0.1943(2) 0.89552(17) 0.0772(5) Uani 1 1 d . . . . .
O3 O 0.82941(17) 0.39284(15) 0.83220(14) 0.0580(4) Uani 1 1 d . . . . .
N1 N 0.64332(19) 0.20631(19) 0.77777(16) 0.0532(4) Uani 1 1 d . . . . .
C1 C 1.0291(3) 0.3339(2) 0.5642(2) 0.0608(6) Uani 1 1 d . . . . .
H1 H 1.1328 0.3660 0.5649 0.073 Uiso 1 1 calc R . . . .
C2 C 0.9932(3) 0.3182(3) 0.4608(2) 0.0669(6) Uani 1 1 d . . . . .
H2 H 1.0719 0.3409 0.3916 0.080 Uiso 1 1 calc R . . . .
C3 C 0.8409(3) 0.2690(3) 0.4600(2) 0.0703(6) Uani 1 1 d . . . . .
H3 H 0.8161 0.2605 0.3894 0.084 Uiso 1 1 calc R . . . .
C4 C 0.7244(3) 0.2321(3) 0.5629(2) 0.0612(5) Uani 1 1 d . . . . .
H4 H 0.6228 0.1956 0.5626 0.073 Uiso 1 1 calc R . . . .
C5 C 0.7588(2) 0.2494(2) 0.66705(19) 0.0507(5) Uani 1 1 d . . . . .
C6 C 0.9123(2) 0.3022(2) 0.66777(19) 0.0503(5) Uani 1 1 d . . . . .
C7 C 0.9490(2) 0.3212(2) 0.7779(2) 0.0528(5) Uani 1 1 d . . . . .
H7 H 1.0634 0.3406 0.7800 0.063 Uiso 1 1 calc R . . . .
C8 C 0.8480(2) 0.2443(2) 0.89731(19) 0.0504(5) Uani 1 1 d . . . . .
C9 C 0.7107(3) 0.1508(2) 0.8942(2) 0.0563(5) Uani 1 1 d . . . . .
H9A H 0.7505 0.0577 0.9071 0.068 Uiso 1 1 calc R . . . .
H9B H 0.6245 0.1407 0.9614 0.068 Uiso 1 1 calc R . . . .
C10 C 0.9145(2) 0.2052(2) 1.0159(2) 0.0535(5) Uani 1 1 d . . . . .
C11 C 1.0093(3) 0.3035(3) 1.0345(2) 0.0681(6) Uani 1 1 d . . . . .
H11 H 1.0319 0.3928 0.9723 0.082 Uiso 1 1 calc R . . . .
C12 C 1.0702(3) 0.2709(3) 1.1430(3) 0.0798(8) Uani 1 1 d . . . . .
H12 H 1.1348 0.3375 1.1533 0.096 Uiso 1 1 calc R . . . .
C13 C 1.0363(3) 0.1412(4) 1.2358(3) 0.0816(8) Uani 1 1 d . . . . .
H13 H 1.0770 0.1198 1.3094 0.098 Uiso 1 1 calc R . . . .
C14 C 0.9416(4) 0.0421(3) 1.2205(2) 0.0792(8) Uani 1 1 d . . . . .
H14 H 0.9183 -0.0461 1.2840 0.095 Uiso 1 1 calc R . . . .
C15 C 0.8807(3) 0.0736(3) 1.1103(2) 0.0658(6) Uani 1 1 d . . . . .
H15 H 0.8173 0.0063 1.1001 0.079 Uiso 1 1 calc R . . . .
C16 C 0.4801(2) 0.4495(2) 0.7614(2) 0.0542(5) Uani 1 1 d . . . . .
C17 C 0.4212(3) 0.4857(3) 0.8590(2) 0.0693(6) Uani 1 1 d . . . . .
H17 H 0.3734 0.4174 0.9335 0.083 Uiso 1 1 calc R . . . .
C18 C 0.4347(4) 0.6255(3) 0.8439(3) 0.0850(8) Uani 1 1 d . . . . .
H18 H 0.3930 0.6509 0.9088 0.102 Uiso 1 1 calc R . . . .
C19 C 0.5079(3) 0.7280(3) 0.7358(3) 0.0790(8) Uani 1 1 d . . . . .
C20 C 0.5668(3) 0.6882(3) 0.6402(3) 0.0747(7) Uani 1 1 d . . . . .
H20 H 0.6179 0.7561 0.5666 0.090 Uiso 1 1 calc R . . . .
C21 C 0.5518(3) 0.5508(3) 0.6509(2) 0.0645(6) Uani 1 1 d . . . . .
H21 H 0.5894 0.5263 0.5847 0.077 Uiso 1 1 calc R . . . .
C22 C 0.5218(4) 0.8807(4) 0.7212(4) 0.1245(15) Uani 1 1 d . . . . .
H22A H 0.5971 0.9327 0.6488 0.187 Uiso 1 1 calc GR . . . .
H22B H 0.5600 0.8852 0.7921 0.187 Uiso 1 1 calc GR . . . .
H22C H 0.4171 0.9211 0.7135 0.187 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 1.4279(18) . ?
S1 O2 1.4255(18) . ?
S1 N1 1.6543(17) . ?
S1 C16 1.759(2) . ?
O3 C7 1.455(2) . ?
O3 C8 1.438(2) . ?
N1 C5 1.436(3) . ?
N1 C9 1.471(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(3) . ?
C1 C6 1.390(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 C6 1.396(3) . ?
C6 C7 1.472(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.471(3) . ?
C8 C9 1.516(3) . ?
C8 C10 1.496(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.391(3) . ?
C10 C15 1.384(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(3) . ?
C16 C21 1.381(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(4) . ?
C19 C20 1.380(4) . ?
C19 C22 1.516(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(4) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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 N1 106.70(10) . . ?
O1 S1 C16 107.42(11) . . ?
O2 S1 O1 119.56(11) . . ?
O2 S1 N1 105.97(10) . . ?
O2 S1 C16 107.81(11) . . ?
N1 S1 C16 109.07(9) . . ?
C8 O3 C7 61.13(13) . . ?
C5 N1 S1 120.71(14) . . ?
C5 N1 C9 116.35(16) . . ?
C9 N1 S1 118.51(14) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.9(2) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 N1 121.59(18) . . ?
C4 C5 C6 119.79(19) . . ?
C6 C5 N1 118.51(19) . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 C7 121.13(19) . . ?
C5 C6 C7 119.93(18) . . ?
O3 C7 C6 116.53(16) . . ?
O3 C7 H7 116.5 . . ?
O3 C7 C8 58.87(12) . . ?
C6 C7 H7 116.5 . . ?
C8 C7 C6 119.40(17) . . ?
C8 C7 H7 116.5 . . ?
O3 C8 C7 60.00(13) . . ?
O3 C8 C9 114.16(16) . . ?
O3 C8 C10 115.29(17) . . ?
C7 C8 C9 115.13(18) . . ?
C7 C8 C10 121.58(17) . . ?
C10 C8 C9 117.50(18) . . ?
N1 C9 C8 113.08(17) . . ?
N1 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C8 119.9(2) . . ?
C15 C10 C8 121.6(2) . . ?
C15 C10 C11 118.4(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.0(2) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 S1 119.61(18) . . ?
C17 C16 C21 120.7(2) . . ?
C21 C16 S1 119.71(18) . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.7(2) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 121.9(3) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 118.1(3) . . ?
C18 C19 C22 121.1(3) . . ?
C20 C19 C22 120.9(3) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.6(3) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 120.5 . . ?
C20 C21 C16 119.0(2) . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 N1 C5 C4 -58.7(2) . . . . ?
S1 N1 C5 C6 125.04(18) . . . . ?
S1 N1 C9 C8 -107.68(18) . . . . ?
S1 C16 C17 C18 -178.78(19) . . . . ?
S1 C16 C21 C20 -179.62(16) . . . . ?
O1 S1 N1 C5 43.79(19) . . . . ?
O1 S1 N1 C9 -160.67(16) . . . . ?
O1 S1 C16 C17 133.88(19) . . . . ?
O1 S1 C16 C21 -45.19(19) . . . . ?
O2 S1 N1 C5 172.22(16) . . . . ?
O2 S1 N1 C9 -32.24(18) . . . . ?
O2 S1 C16 C17 3.8(2) . . . . ?
O2 S1 C16 C21 -175.27(17) . . . . ?
O3 C7 C8 C9 104.55(19) . . . . ?
O3 C7 C8 C10 -103.0(2) . . . . ?
O3 C8 C9 N1 34.6(3) . . . . ?
O3 C8 C10 C11 -24.6(3) . . . . ?
O3 C8 C10 C15 153.71(19) . . . . ?
N1 S1 C16 C17 -110.84(19) . . . . ?
N1 S1 C16 C21 70.09(19) . . . . ?
N1 C5 C6 C1 175.04(18) . . . . ?
N1 C5 C6 C7 -3.9(3) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C1 C6 C7 O3 133.2(2) . . . . ?
C1 C6 C7 C8 -159.21(19) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
C2 C1 C6 C7 -178.9(2) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C3 C4 C5 N1 -177.2(2) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 C7 179.77(19) . . . . ?
C5 N1 C9 C8 48.9(2) . . . . ?
C5 C6 C7 O3 -47.9(3) . . . . ?
C5 C6 C7 C8 19.7(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C6 C7 C8 O3 -105.0(2) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C6 C7 C8 C10 152.06(19) . . . . ?
C7 O3 C8 C9 -106.2(2) . . . . ?
C7 O3 C8 C10 113.33(19) . . . . ?
C7 C8 C9 N1 -32.2(2) . . . . ?
C7 C8 C10 C11 44.4(3) . . . . ?
C7 C8 C10 C15 -137.3(2) . . . . ?
C8 O3 C7 C6 109.8(2) . . . . ?
C8 C10 C11 C12 179.2(2) . . . . ?
C8 C10 C15 C14 -178.5(2) . . . . ?
C9 N1 C5 C4 145.3(2) . . . . ?
C9 N1 C5 C6 -31.0(3) . . . . ?
C9 C8 C10 C11 -163.7(2) . . . . ?
C9 C8 C10 C15 14.6(3) . . . . ?
C10 C8 C9 N1 174.15(16) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C10 -0.4(4) . . . . ?
C15 C10 C11 C12 0.9(4) . . . . ?
C16 S1 N1 C5 -71.96(17) . . . . ?
C16 S1 N1 C9 83.58(17) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
C17 C16 C21 C20 1.3(3) . . . . ?
C17 C18 C19 C20 0.9(4) . . . . ?
C17 C18 C19 C22 -179.9(3) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
C19 C20 C21 C16 -1.9(4) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
C22 C19 C20 C21 -178.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.096
_oxdiff_exptl_absorpt_empirical_full_min 0.910
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_20230478_auto
_database_code_depnum_ccdc_archive 'CCDC 2255452'
loop_
_audit_author_name
_audit_author_address
'Zhen-Hua Wang'
;Chengdu University
China
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-07-15 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C37 H30 N2 O3 S'
_chemical_formula_sum            'C37 H30 N2 O3 S'
_chemical_formula_weight         582.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N1O1S1
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/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                   13.5153(3)
_cell_length_b                   7.31558(19)
_cell_length_c                   30.8108(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.412(2)
_cell_angle_gamma                90
_cell_volume                     3013.55(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3029
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.6400
_cell_measurement_theta_min      5.0620
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    1.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10849
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.410
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -35.00   1.00    3.50    --  -33.50 178.00-150.00   73
  2  ω    -26.00  19.00   1.00    3.50    --  -33.50  57.00 -60.00   45
  3  ω    -52.00  35.00   1.00    3.50    --  -33.50  57.00   0.00   87
  4  ω   -101.00 -15.00   1.00    3.50    --  -33.50 -57.00-150.00   86
  5  ω   -108.00 -78.00   1.00    3.50    --  -33.50 178.00 -60.00   30
  6  ω     84.00 110.00   1.00    3.50    --   36.47 178.00-150.00   26
  7  ω     22.00  61.00   1.00    3.50    --   36.47  57.00 150.00   39
  8  ω     37.00 125.00   1.00   12.50    --  108.00 -30.00-180.00   88
  9  ω    100.00 162.00   1.00   12.50    --  108.00  61.00   0.00   62
 10  ω     38.00  90.00   1.00   12.50    --  108.00 -94.00 120.00   52
 11  ω     52.00 101.00   1.00   12.50    --  108.00 -94.00-180.00   49
 12  ω     41.00  86.00   1.00   12.50    --  108.00 -94.00 -30.00   45
 13  ω     37.00  85.00   1.00   12.50    --  108.00 -30.00 -90.00   48
 14  ω     76.00 130.00   1.00   12.50    --  108.00 178.00 120.00   54
 15  ω     42.00 124.00   1.00   12.50    --  108.00 -61.00-180.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0896720000
_diffrn_orient_matrix_UB_12      0.0245901000
_diffrn_orient_matrix_UB_13      -0.0365946000
_diffrn_orient_matrix_UB_21      0.0670534000
_diffrn_orient_matrix_UB_22      -0.0497218000
_diffrn_orient_matrix_UB_23      -0.0346106000
_diffrn_orient_matrix_UB_31      -0.0272975000
_diffrn_orient_matrix_UB_32      -0.2031607000
_diffrn_orient_matrix_UB_33      0.0040280000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3647
_reflns_number_total             5374
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.017
_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)+(0.0706P)²+0.3557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1571
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42829(5) 0.49156(13) 0.40322(3) 0.0792(3) Uani 1 1 d . . . . .
O1 O 0.87937(14) 0.4888(3) 0.34591(6) 0.0799(6) Uani 1 1 d . . . . .
O2 O 0.39905(16) 0.3063(4) 0.39374(9) 0.1065(9) Uani 1 1 d . . . . .
O3 O 0.37454(17) 0.6019(4) 0.42953(8) 0.1118(10) Uani 1 1 d . . . . .
N1 N 0.95571(15) 0.3515(3) 0.40911(7) 0.0620(6) Uani 1 1 d . . . . .
N2 N 0.54462(15) 0.4823(3) 0.42831(7) 0.0602(5) Uani 1 1 d . . . . .
C1 C 0.8040(2) 0.3866(4) 0.49510(8) 0.0582(6) Uani 1 1 d . . . . .
H1 H 0.7416 0.4342 0.4982 0.070 Uiso 1 1 calc R . . . .
C2 C 0.8649(2) 0.3120(4) 0.53100(9) 0.0669(7) Uani 1 1 d . . . . .
H2 H 0.8424 0.3076 0.5581 0.080 Uiso 1 1 calc R . . . .
C3 C 0.9585(2) 0.2444(4) 0.52695(9) 0.0751(8) Uani 1 1 d . . . . .
H3 H 0.9980 0.1941 0.5513 0.090 Uiso 1 1 calc R . . . .
C4 C 0.9940(2) 0.2507(4) 0.48714(10) 0.0675(7) Uani 1 1 d . . . . .
H4 H 1.0573 0.2062 0.4844 0.081 Uiso 1 1 calc R . . . .
C5 C 0.93362(18) 0.3244(3) 0.45169(8) 0.0548(6) Uani 1 1 d . . . . .
C6 C 0.83721(18) 0.3891(3) 0.45470(8) 0.0521(5) Uani 1 1 d . . . . .
C7 C 0.79431(17) 0.4522(4) 0.41017(8) 0.0541(6) Uani 1 1 d . . . . .
C8 C 0.87833(18) 0.4352(4) 0.38329(8) 0.0603(6) Uani 1 1 d . . . . .
C9 C 0.7314(2) 0.8509(4) 0.45466(10) 0.0747(8) Uani 1 1 d . . . . .
H9 H 0.7893 0.8942 0.4452 0.090 Uiso 1 1 calc R . . . .
C10 C 0.6966(3) 0.9330(4) 0.48991(12) 0.0913(11) Uani 1 1 d . . . . .
H10 H 0.7316 1.0306 0.5041 0.110 Uiso 1 1 calc R . . . .
C11 C 0.6111(3) 0.8719(5) 0.50406(12) 0.0927(11) Uani 1 1 d . . . . .
H11 H 0.5883 0.9284 0.5278 0.111 Uiso 1 1 calc R . . . .
C12 C 0.5589(3) 0.7280(4) 0.48352(10) 0.0787(8) Uani 1 1 d . . . . .
H12 H 0.5008 0.6871 0.4932 0.094 Uiso 1 1 calc R . . . .
C13 C 0.5930(2) 0.6432(4) 0.44806(8) 0.0597(6) Uani 1 1 d . . . . .
C14 C 0.67992(19) 0.7035(3) 0.43315(8) 0.0574(6) Uani 1 1 d . . . . .
C15 C 0.71963(18) 0.6056(4) 0.39727(8) 0.0567(6) Uani 1 1 d . . . . .
H15 H 0.7319 0.6808 0.3723 0.068 Uiso 1 1 calc R . . . .
C16 C 0.68601(17) 0.4147(4) 0.38677(8) 0.0531(6) Uani 1 1 d . . . . .
C17 C 0.61157(18) 0.3410(4) 0.41523(8) 0.0566(6) Uani 1 1 d . . . . .
H17A H 0.5716 0.2460 0.3992 0.068 Uiso 1 1 calc R . . . .
H17B H 0.6482 0.2859 0.4414 0.068 Uiso 1 1 calc R . . . .
C18 C 1.05403(19) 0.3311(4) 0.39591(10) 0.0693(7) Uani 1 1 d . . . . .
H18A H 1.1040 0.3639 0.4206 0.083 Uiso 1 1 calc R . . . .
H18B H 1.0597 0.4173 0.3725 0.083 Uiso 1 1 calc R . . . .
C19 C 1.07770(19) 0.1436(4) 0.38057(8) 0.0585(6) Uani 1 1 d . . . . .
C20 C 1.0059(2) 0.0207(4) 0.36284(10) 0.0765(8) Uani 1 1 d . . . . .
H20 H 0.9385 0.0495 0.3615 0.092 Uiso 1 1 calc R . . . .
C21 C 1.0340(4) -0.1473(5) 0.34690(11) 0.1007(12) Uani 1 1 d . . . . .
H21 H 0.9858 -0.2306 0.3348 0.121 Uiso 1 1 calc R . . . .
C22 C 1.1339(4) -0.1879(6) 0.34935(14) 0.1128(15) Uani 1 1 d . . . . .
H22 H 1.1532 -0.2990 0.3385 0.135 Uiso 1 1 calc R . . . .
C23 C 1.2046(4) -0.0685(6) 0.36724(17) 0.1174(15) Uani 1 1 d . . . . .
H23 H 1.2720 -0.0974 0.3687 0.141 Uiso 1 1 calc R . . . .
C24 C 1.1766(2) 0.0945(5) 0.38307(13) 0.0873(10) Uani 1 1 d . . . . .
H24 H 1.2257 0.1747 0.3959 0.105 Uiso 1 1 calc R . . . .
C25 C 0.67476(18) 0.3375(4) 0.34118(8) 0.0625(7) Uani 1 1 d . . . . .
C26 C 0.6421(2) 0.4415(5) 0.30464(9) 0.0803(9) Uani 1 1 d . . . . .
H26 H 0.6273 0.5646 0.3076 0.096 Uiso 1 1 calc R . . . .
C27 C 0.6314(3) 0.3616(8) 0.26313(11) 0.1043(13) Uani 1 1 d . . . . .
H27 H 0.6085 0.4315 0.2385 0.125 Uiso 1 1 calc R . . . .
C28 C 0.6542(3) 0.1810(8) 0.25835(11) 0.1057(14) Uani 1 1 d . . . . .
H28 H 0.6481 0.1291 0.2305 0.127 Uiso 1 1 calc R . . . .
C29 C 0.6861(3) 0.0773(6) 0.29460(13) 0.1009(12) Uani 1 1 d . . . . .
H29 H 0.7007 -0.0457 0.2913 0.121 Uiso 1 1 calc R . . . .
C30 C 0.6967(2) 0.1536(5) 0.33606(10) 0.0783(8) Uani 1 1 d . . . . .
H30 H 0.7185 0.0821 0.3605 0.094 Uiso 1 1 calc R . . . .
C31 C 0.4270(2) 0.6056(5) 0.35264(10) 0.0739(8) Uani 1 1 d . . . . .
C32 C 0.4554(2) 0.7866(5) 0.35195(11) 0.0817(9) Uani 1 1 d . . . . .
H32 H 0.4774 0.8480 0.3780 0.098 Uiso 1 1 calc R . . . .
C33 C 0.4508(3) 0.8756(6) 0.31238(12) 0.0947(11) Uani 1 1 d . . . . .
H33 H 0.4706 0.9974 0.3121 0.114 Uiso 1 1 calc R . . . .
C34 C 0.4179(3) 0.7898(8) 0.27334(13) 0.1055(13) Uani 1 1 d . . . . .
C35 C 0.3898(3) 0.6087(8) 0.27468(13) 0.1139(14) Uani 1 1 d . . . . .
H35 H 0.3673 0.5481 0.2486 0.137 Uiso 1 1 calc R . . . .
C36 C 0.3945(3) 0.5148(6) 0.31423(12) 0.0967(11) Uani 1 1 d . . . . .
H36 H 0.3759 0.3925 0.3146 0.116 Uiso 1 1 calc R . . . .
C37 C 0.4127(4) 0.8888(9) 0.22989(14) 0.154(2) Uani 1 1 d . . . . .
H37A H 0.4771 0.8860 0.2203 0.231 Uiso 1 1 calc GR . . . .
H37B H 0.3930 1.0135 0.2334 0.231 Uiso 1 1 calc GR . . . .
H37C H 0.3645 0.8298 0.2084 0.231 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 O2 1.430(3) . ?
S1 O3 1.418(3) . ?
S1 N2 1.649(2) . ?
S1 C31 1.766(3) . ?
O1 C8 1.219(3) . ?
N1 C5 1.402(3) . ?
N1 C8 1.363(3) . ?
N1 C18 1.453(3) . ?
N2 C13 1.437(3) . ?
N2 C17 1.469(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.390(4) . ?
C1 C6 1.384(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(4) . ?
C5 C6 1.402(3) . ?
C6 C7 1.483(3) . ?
C7 C8 1.505(3) . ?
C7 C15 1.523(3) . ?
C7 C16 1.558(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(5) . ?
C9 C14 1.397(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.368(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.392(4) . ?
C13 C14 1.394(4) . ?
C14 C15 1.482(4) . ?
C15 H15 0.9800 . ?
C15 C16 1.490(4) . ?
C16 C17 1.526(3) . ?
C16 C25 1.501(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.500(4) . ?
C19 C20 1.376(4) . ?
C19 C24 1.376(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.397(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.351(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.363(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(4) . ?
C25 C30 1.391(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.394(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.370(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.366(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.382(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(5) . ?
C31 C36 1.372(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.375(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.372(6) . ?
C34 C35 1.381(6) . ?
C34 C37 1.515(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.392(5) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 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
O2 S1 N2 105.85(14) . . ?
O2 S1 C31 107.51(17) . . ?
O3 S1 O2 120.49(17) . . ?
O3 S1 N2 106.77(15) . . ?
O3 S1 C31 107.23(16) . . ?
N2 S1 C31 108.57(12) . . ?
C5 N1 C18 125.2(2) . . ?
C8 N1 C5 111.1(2) . . ?
C8 N1 C18 122.5(2) . . ?
C13 N2 S1 120.56(18) . . ?
C13 N2 C17 115.6(2) . . ?
C17 N2 S1 118.93(18) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C6 C1 C2 119.2(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C6 110.0(2) . . ?
C4 C5 N1 128.0(2) . . ?
C4 C5 C6 122.0(3) . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 134.6(2) . . ?
C5 C6 C7 106.6(2) . . ?
C6 C7 C8 105.0(2) . . ?
C6 C7 C15 128.7(2) . . ?
C6 C7 C16 125.9(2) . . ?
C8 C7 C15 116.2(2) . . ?
C8 C7 C16 117.7(2) . . ?
C15 C7 C16 57.81(16) . . ?
O1 C8 N1 125.6(2) . . ?
O1 C8 C7 127.4(2) . . ?
N1 C8 C7 107.0(2) . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C14 120.3(3) . . ?
C14 C9 H9 119.8 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 N2 121.0(3) . . ?
C12 C13 C14 120.6(3) . . ?
C14 C13 N2 118.2(2) . . ?
C9 C14 C15 121.2(3) . . ?
C13 C14 C9 118.2(3) . . ?
C13 C14 C15 120.5(2) . . ?
C7 C15 H15 115.9 . . ?
C14 C15 C7 117.4(2) . . ?
C14 C15 H15 115.9 . . ?
C14 C15 C16 118.9(2) . . ?
C16 C15 C7 62.28(16) . . ?
C16 C15 H15 115.9 . . ?
C15 C16 C7 59.91(16) . . ?
C15 C16 C17 114.4(2) . . ?
C15 C16 C25 122.8(2) . . ?
C17 C16 C7 116.7(2) . . ?
C25 C16 C7 117.3(2) . . ?
C25 C16 C17 114.8(2) . . ?
N2 C17 C16 113.1(2) . . ?
N2 C17 H17A 109.0 . . ?
N2 C17 H17B 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
N1 C18 H18A 108.4 . . ?
N1 C18 H18B 108.4 . . ?
N1 C18 C19 115.3(2) . . ?
H18A C18 H18B 107.5 . . ?
C19 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C20 C19 C18 123.5(3) . . ?
C24 C19 C18 118.1(3) . . ?
C24 C19 C20 118.3(3) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.1(4) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.9(4) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.7(4) . . ?
C24 C23 H23 120.2 . . ?
C19 C24 H24 119.1 . . ?
C23 C24 C19 121.8(4) . . ?
C23 C24 H24 119.1 . . ?
C26 C25 C16 122.3(3) . . ?
C26 C25 C30 119.3(3) . . ?
C30 C25 C16 118.4(3) . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.8(4) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.5(4) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.8(3) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.6(4) . . ?
C30 C29 H29 119.7 . . ?
C25 C30 H30 120.0 . . ?
C29 C30 C25 120.0(4) . . ?
C29 C30 H30 120.0 . . ?
C32 C31 S1 120.0(3) . . ?
C36 C31 S1 119.5(3) . . ?
C36 C31 C32 120.4(3) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 C31 119.4(4) . . ?
C33 C32 H32 120.3 . . ?
C32 C33 H33 119.1 . . ?
C34 C33 C32 121.8(4) . . ?
C34 C33 H33 119.1 . . ?
C33 C34 C35 117.9(4) . . ?
C33 C34 C37 121.6(5) . . ?
C35 C34 C37 120.5(5) . . ?
C34 C35 H35 119.3 . . ?
C34 C35 C36 121.5(4) . . ?
C36 C35 H35 119.3 . . ?
C31 C36 C35 118.9(4) . . ?
C31 C36 H36 120.5 . . ?
C35 C36 H36 120.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 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 N2 C13 C12 64.8(3) . . . . ?
S1 N2 C13 C14 -120.4(2) . . . . ?
S1 N2 C17 C16 103.6(2) . . . . ?
S1 C31 C32 C33 -177.8(2) . . . . ?
S1 C31 C36 C35 177.3(3) . . . . ?
O2 S1 N2 C13 -171.2(2) . . . . ?
O2 S1 N2 C17 34.6(2) . . . . ?
O2 S1 C31 C32 -178.0(2) . . . . ?
O2 S1 C31 C36 4.2(3) . . . . ?
O3 S1 N2 C13 -41.7(2) . . . . ?
O3 S1 N2 C17 164.2(2) . . . . ?
O3 S1 C31 C32 51.1(3) . . . . ?
O3 S1 C31 C36 -126.7(3) . . . . ?
N1 C5 C6 C1 -175.5(2) . . . . ?
N1 C5 C6 C7 3.1(3) . . . . ?
N1 C18 C19 C20 25.8(4) . . . . ?
N1 C18 C19 C24 -156.4(3) . . . . ?
N2 S1 C31 C32 -63.9(3) . . . . ?
N2 S1 C31 C36 118.3(3) . . . . ?
N2 C13 C14 C9 -175.0(2) . . . . ?
N2 C13 C14 C15 1.2(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C6 C7 C8 172.6(3) . . . . ?
C1 C6 C7 C15 29.4(5) . . . . ?
C1 C6 C7 C16 -45.4(4) . . . . ?
C2 C1 C6 C5 -3.1(4) . . . . ?
C2 C1 C6 C7 178.8(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 N1 177.0(3) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C4 C5 C6 C1 3.1(4) . . . . ?
C4 C5 C6 C7 -178.3(2) . . . . ?
C5 N1 C8 O1 173.9(3) . . . . ?
C5 N1 C8 C7 -4.6(3) . . . . ?
C5 N1 C18 C19 90.2(3) . . . . ?
C5 C6 C7 C8 -5.6(3) . . . . ?
C5 C6 C7 C15 -148.9(2) . . . . ?
C5 C6 C7 C16 136.4(2) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
C6 C7 C8 O1 -172.2(3) . . . . ?
C6 C7 C8 N1 6.3(3) . . . . ?
C6 C7 C15 C14 -2.6(4) . . . . ?
C6 C7 C15 C16 -112.6(3) . . . . ?
C6 C7 C16 C15 117.1(3) . . . . ?
C6 C7 C16 C17 13.1(4) . . . . ?
C6 C7 C16 C25 -128.9(3) . . . . ?
C7 C15 C16 C17 108.0(2) . . . . ?
C7 C15 C16 C25 -104.9(2) . . . . ?
C7 C16 C17 N2 100.3(3) . . . . ?
C7 C16 C25 C26 -105.7(3) . . . . ?
C7 C16 C25 C30 75.4(3) . . . . ?
C8 N1 C5 C4 -177.5(3) . . . . ?
C8 N1 C5 C6 1.0(3) . . . . ?
C8 N1 C18 C19 -103.4(3) . . . . ?
C8 C7 C15 C14 -142.5(2) . . . . ?
C8 C7 C15 C16 107.5(2) . . . . ?
C8 C7 C16 C15 -105.1(3) . . . . ?
C8 C7 C16 C17 151.0(2) . . . . ?
C8 C7 C16 C25 8.9(3) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C9 C14 C15 C7 85.7(3) . . . . ?
C9 C14 C15 C16 157.5(2) . . . . ?
C10 C9 C14 C13 0.4(4) . . . . ?
C10 C9 C14 C15 -175.8(3) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 N2 174.6(3) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C9 -0.2(4) . . . . ?
C12 C13 C14 C15 176.1(2) . . . . ?
C13 N2 C17 C16 -51.8(3) . . . . ?
C13 C14 C15 C7 -90.4(3) . . . . ?
C13 C14 C15 C16 -18.6(3) . . . . ?
C14 C9 C10 C11 -0.4(5) . . . . ?
C14 C15 C16 C7 -107.7(2) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C14 C15 C16 C25 147.4(2) . . . . ?
C15 C7 C8 O1 -23.5(4) . . . . ?
C15 C7 C8 N1 154.9(2) . . . . ?
C15 C7 C16 C17 -104.0(2) . . . . ?
C15 C7 C16 C25 113.9(3) . . . . ?
C15 C16 C17 N2 33.2(3) . . . . ?
C15 C16 C25 C26 -35.5(4) . . . . ?
C15 C16 C25 C30 145.6(3) . . . . ?
C16 C7 C8 O1 42.1(4) . . . . ?
C16 C7 C8 N1 -139.5(2) . . . . ?
C16 C7 C15 C14 110.0(2) . . . . ?
C16 C25 C26 C27 -178.8(3) . . . . ?
C16 C25 C30 C29 179.2(3) . . . . ?
C17 N2 C13 C12 -140.2(3) . . . . ?
C17 N2 C13 C14 34.5(3) . . . . ?
C17 C16 C25 C26 111.5(3) . . . . ?
C17 C16 C25 C30 -67.4(3) . . . . ?
C18 N1 C5 C4 -9.8(4) . . . . ?
C18 N1 C5 C6 168.6(2) . . . . ?
C18 N1 C8 O1 5.8(5) . . . . ?
C18 N1 C8 C7 -172.6(2) . . . . ?
C18 C19 C20 C21 176.2(3) . . . . ?
C18 C19 C24 C23 -175.7(4) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C19 C24 C23 2.2(5) . . . . ?
C20 C21 C22 C23 0.6(6) . . . . ?
C21 C22 C23 C24 0.0(7) . . . . ?
C22 C23 C24 C19 -1.4(7) . . . . ?
C24 C19 C20 C21 -1.6(5) . . . . ?
C25 C16 C17 N2 -116.7(2) . . . . ?
C25 C26 C27 C28 -0.8(5) . . . . ?
C26 C25 C30 C29 0.3(4) . . . . ?
C26 C27 C28 C29 1.2(6) . . . . ?
C27 C28 C29 C30 -0.8(6) . . . . ?
C28 C29 C30 C25 0.1(5) . . . . ?
C30 C25 C26 C27 0.1(4) . . . . ?
C31 S1 N2 C13 73.6(2) . . . . ?
C31 S1 N2 C17 -80.5(2) . . . . ?
C31 C32 C33 C34 0.6(5) . . . . ?
C32 C31 C36 C35 -0.5(5) . . . . ?
C32 C33 C34 C35 -0.5(6) . . . . ?
C32 C33 C34 C37 179.7(4) . . . . ?
C33 C34 C35 C36 -0.1(6) . . . . ?
C34 C35 C36 C31 0.6(6) . . . . ?
C36 C31 C32 C33 0.0(5) . . . . ?
C37 C34 C35 C36 179.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.898
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
