# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_wangshunch_0222-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2206616'
loop_
_audit_author_name
_audit_author_address
Hui
;Lanzhou University 
China
;
_audit_update_record             
;
2022-09-12 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_audit_creation_date             2022-02-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 O4 S'
_chemical_formula_sum            'C21 H18 N O4 S'
_chemical_formula_weight         380.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.4800(3)
_cell_length_b                   10.7260(5)
_cell_length_c                   11.5506(5)
_cell_angle_alpha                94.424(4)
_cell_angle_beta                 109.645(4)
_cell_angle_gamma                96.794(3)
_cell_volume                     974.79(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9076
_cell_measurement_temperature    295.83(10)
_cell_measurement_theta_max      77.1660
_cell_measurement_theta_min      4.1060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11134
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.459
_diffrn_reflns_theta_min         4.096
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.83(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00 117.00   0.50    0.05    --   47.57  67.00 -46.00  154
  2  ω    104.00 169.00   0.50    0.05    --  107.75  37.00-120.00  130
  3  ω     91.00 118.00   0.50    0.05    --  107.75  67.00 -46.00   54
  4  ω    120.00 171.00   0.50    0.05    --  107.75  67.00 -46.00  102
  5  ω     99.00 172.00   0.50    0.05    --  107.75  19.00  90.00  146
  6  ω     37.00 110.00   0.50    0.05    --  107.75-125.00  90.00  146
  7  ω     81.00 106.00   0.50    0.05    --  107.75 -99.00 120.00   50
  8  ω     38.00  63.00   0.50    0.05    --  107.75 -99.00 120.00   50
  9  ω     44.00 104.00   0.50    0.05    --  107.75 -99.00  90.00  120
 10  ω     35.00  81.00   0.50    0.05    --  107.75 -99.00-150.00   92
 11  ω    -12.00  23.00   0.50    0.05    --   47.57 -19.00-180.00   70
 12  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00-180.00   50
 13  ω     36.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   50
 14  ω     36.00  93.00   0.50    0.05    --  107.75 -77.00 120.00  114
 15  ω     49.00  77.00   0.50    0.05    --  107.75 -67.00 179.00   56
 16  ω    -15.00  34.00   0.50    0.05    --   47.57 -67.00 179.00   98
 17  ω    -28.00  19.00   0.50    0.05    --  -47.57  19.00 -90.00   94
 18  ω    -65.00   2.00   0.50    0.05    --  -47.57  67.00 -46.00  134
 19  ω    -63.00 -38.00   0.50    0.05    -- -100.00  57.00-180.00   50
 20  ω    -81.00 -27.00   0.50    0.05    -- -100.00  67.00 -46.00  108
 21  ω    -91.00 -29.00   0.50    0.05    -- -100.00  77.00   0.00  124
 22  ω    -65.00 -40.00   0.50    0.05    -- -100.00  57.00  60.00   50
 23  ω    -56.00 -28.00   0.50    0.05    -- -100.00  57.00 150.00   56
 24  ω    -87.00 -33.00   0.50    0.05    --  -47.57 125.00 -30.00  108
 25  ω   -111.00 -85.00   0.50    0.05    -- -100.00 125.00   0.00   52
 26  ω    -95.00 -32.00   0.50    0.05    -- -100.00 125.00 -30.00  126
 27  ω    -53.00 -27.00   0.50    0.05    -- -100.00 125.00   0.00   52
 28  ω   -112.00 -69.00   0.50    0.05    -- -100.00 125.00 -60.00   86
 29  ω   -112.00 -46.00   0.50    0.05    -- -100.00 125.00-120.00  132
 30  ω   -112.00 -72.00   0.50    0.05    -- -100.00 125.00-180.00   80
 31  ω   -147.00-111.00   0.50    0.05    -- -100.00 -57.00 -30.00   72
 32  ω   -171.00 -85.00   0.50    0.05    -- -100.00 -57.00-120.00  172
 33  ω   -112.00 -31.00   0.50    0.05    --  -47.57 -67.00 179.00  162
 34  ω   -159.00 -83.00   0.50    0.05    -- -100.00 -67.00 179.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0208275000
_diffrn_orient_matrix_UB_12      -0.1311729000
_diffrn_orient_matrix_UB_13      0.0435139000
_diffrn_orient_matrix_UB_21      0.1771744000
_diffrn_orient_matrix_UB_22      0.0334669000
_diffrn_orient_matrix_UB_23      0.1007905000
_diffrn_orient_matrix_UB_31      -0.0792751000
_diffrn_orient_matrix_UB_32      0.0541114000
_diffrn_orient_matrix_UB_33      0.0912250000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3572
_reflns_number_total             3899
_reflns_odcompleteness_completeness 99.37
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0722P)²+0.1253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.43209(4) 0.20984(4) 0.42460(3) 0.05495(15) Uani 1 1 d . . . . .
O1 O 0.23831(13) 0.02281(11) 0.21176(11) 0.0614(3) Uani 1 1 d . . . . .
O2 O 0.34872(13) 0.09833(11) 0.07486(10) 0.0586(3) Uani 1 1 d . . . . .
O3 O 0.20955(13) 0.30215(11) 0.16512(12) 0.0658(3) Uani 1 1 d . . . . .
O4 O 0.49272(11) 0.31111(9) 0.23358(9) 0.0481(2) Uani 1 1 d . . . . .
C1 C 0.47921(16) 0.19198(13) 0.28055(12) 0.0443(3) Uani 1 1 d . . . . .
C2 C 0.33646(16) 0.09521(13) 0.18629(13) 0.0479(3) Uani 1 1 d . . . . .
C3 C 0.2201(2) 0.0178(2) -0.02685(18) 0.0761(5) Uani 1 1 d . . . . .
H3A H 0.262610 0.002057 -0.092975 0.114 Uiso 1 1 calc R U . . .
H3B H 0.121683 0.058641 -0.055786 0.114 Uiso 1 1 calc R U . . .
H3C H 0.190247 -0.060994 0.000435 0.114 Uiso 1 1 calc R U . . .
C4 C 0.64657(16) 0.14316(13) 0.30171(12) 0.0432(3) Uani 1 1 d . . . . .
C5 C 0.66161(19) 0.02315(15) 0.33703(14) 0.0543(3) Uani 1 1 d . . . . .
H5 H 0.569710 -0.025827 0.346536 0.065 Uiso 1 1 calc R U . . .
C6 C 0.8124(2) -0.02420(16) 0.35822(15) 0.0594(4) Uani 1 1 d . . . . .
H6 H 0.821514 -0.104720 0.381936 0.071 Uiso 1 1 calc R U . . .
C7 C 0.94914(19) 0.04780(17) 0.34422(14) 0.0583(4) Uani 1 1 d . . . . .
H7 H 1.050613 0.016139 0.358705 0.070 Uiso 1 1 calc R U . . .
C8 C 0.93492(18) 0.16626(16) 0.30886(15) 0.0578(4) Uani 1 1 d . . . . .
H8 H 1.026994 0.214623 0.298981 0.069 Uiso 1 1 calc R U . . .
C9 C 0.78409(17) 0.21477(14) 0.28764(14) 0.0504(3) Uani 1 1 d . . . . .
H9 H 0.775716 0.295369 0.263997 0.061 Uiso 1 1 calc R U . . .
C10 C 0.63218(19) 0.28854(15) 0.52726(14) 0.0531(3) Uani 1 1 d . . . . .
C11 C 0.7324(2) 0.22312(19) 0.61443(17) 0.0674(4) Uani 1 1 d . . . . .
H11 H 0.695600 0.138659 0.617487 0.081 Uiso 1 1 calc R U . . .
C12 C 0.8867(3) 0.2824(3) 0.6969(2) 0.0931(7) Uani 1 1 d . . . . .
H12 H 0.953002 0.238492 0.756540 0.112 Uiso 1 1 calc R U . . .
C13 C 0.9425(3) 0.4063(3) 0.6910(3) 0.1009(8) Uani 1 1 d . . . . .
H13 H 1.047269 0.445850 0.746348 0.121 Uiso 1 1 calc R U . . .
C14 C 0.8453(3) 0.4722(2) 0.6044(3) 0.0966(7) Uani 1 1 d . . . . .
H14 H 0.884826 0.555851 0.600350 0.116 Uiso 1 1 calc R U . . .
C15 C 0.6877(3) 0.41432(17) 0.52262(19) 0.0724(5) Uani 1 1 d . . . . .
H15 H 0.619968 0.459552 0.465184 0.087 Uiso 1 1 calc R U . . .
C16 C 0.34727(18) 0.35869(14) 0.18033(14) 0.0506(3) Uani 1 1 d . . . . .
C17 C 0.38041(19) 0.48505(14) 0.14281(15) 0.0530(3) Uani 1 1 d . . . . .
C18 C 0.5399(2) 0.55410(17) 0.1767(2) 0.0740(5) Uani 1 1 d . . . . .
H18 H 0.633414 0.522170 0.226459 0.089 Uiso 1 1 calc R U . . .
C19 C 0.5606(3) 0.6709(2) 0.1368(3) 0.0911(7) Uani 1 1 d . . . . .
H19 H 0.668586 0.717367 0.159941 0.109 Uiso 1 1 calc R U . . .
C20 C 0.4252(3) 0.7189(2) 0.0639(3) 0.0917(7) Uani 1 1 d . . . . .
H20 H 0.440477 0.798119 0.038250 0.110 Uiso 1 1 calc R U . . .
C21 C 0.2658(3) 0.6501(2) 0.0284(3) 0.0948(7) Uani 1 1 d . . . . .
H21 H 0.172971 0.682073 -0.022291 0.114 Uiso 1 1 calc R U . . .
C22 C 0.2436(2) 0.53369(19) 0.0681(2) 0.0766(5) Uani 1 1 d . . . . .
H22 H 0.135478 0.487410 0.044243 0.092 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.8388(14) . ?
S1 C10 1.7753(16) . ?
O1 C2 1.1955(17) . ?
O2 C2 1.3283(18) . ?
O2 C3 1.440(2) . ?
O3 C16 1.2003(18) . ?
O4 C1 1.4333(15) . ?
O4 C16 1.3592(16) . ?
C1 C2 1.5396(19) . ?
C1 C4 1.5200(17) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.387(2) . ?
C4 C9 1.3824(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(2) . ?
C10 C15 1.387(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.479(2) . ?
C17 C18 1.376(2) . ?
C17 C22 1.379(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.360(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(3) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C1 99.56(6) . . ?
C2 O2 C3 117.08(13) . . ?
C16 O4 C1 117.67(10) . . ?
O4 C1 S1 110.87(9) . . ?
O4 C1 C2 111.04(10) . . ?
O4 C1 C4 107.17(10) . . ?
C2 C1 S1 107.85(9) . . ?
C4 C1 S1 111.30(9) . . ?
C4 C1 C2 108.61(11) . . ?
O1 C2 O2 125.70(14) . . ?
O1 C2 C1 124.91(13) . . ?
O2 C2 C1 109.19(11) . . ?
O2 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
O2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C1 118.75(12) . . ?
C9 C4 C1 122.11(12) . . ?
C9 C4 C5 119.13(12) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.46(14) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.10(15) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.73(14) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.59(14) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 119.98(14) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 S1 118.94(13) . . ?
C11 C10 C15 119.73(17) . . ?
C15 C10 S1 121.32(13) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 119.5(2) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
O3 C16 O4 122.85(13) . . ?
O3 C16 C17 125.16(13) . . ?
O4 C16 C17 111.98(12) . . ?
C18 C17 C16 123.29(14) . . ?
C18 C17 C22 119.12(15) . . ?
C22 C17 C16 117.58(14) . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.82(18) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.78(18) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.84(19) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.60(19) . . ?
C21 C22 H22 119.7 . . ?

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 C1 C2 O1 -16.91(17) . . . . ?
S1 C1 C2 O2 168.02(9) . . . . ?
S1 C1 C4 C5 64.23(15) . . . . ?
S1 C1 C4 C9 -115.35(13) . . . . ?
S1 C10 C11 C12 -178.69(16) . . . . ?
S1 C10 C15 C14 -179.84(16) . . . . ?
O3 C16 C17 C18 170.79(18) . . . . ?
O3 C16 C17 C22 -10.5(3) . . . . ?
O4 C1 C2 O1 -138.58(14) . . . . ?
O4 C1 C2 O2 46.35(14) . . . . ?
O4 C1 C4 C5 -174.40(12) . . . . ?
O4 C1 C4 C9 6.03(18) . . . . ?
O4 C16 C17 C18 -10.2(2) . . . . ?
O4 C16 C17 C22 168.55(15) . . . . ?
C1 S1 C10 C11 -108.10(13) . . . . ?
C1 S1 C10 C15 72.97(14) . . . . ?
C1 O4 C16 O3 -4.3(2) . . . . ?
C1 O4 C16 C17 176.60(12) . . . . ?
C1 C4 C5 C6 -179.44(14) . . . . ?
C1 C4 C9 C8 179.57(13) . . . . ?
C2 C1 C4 C5 -54.36(16) . . . . ?
C2 C1 C4 C9 126.06(14) . . . . ?
C3 O2 C2 O1 7.8(2) . . . . ?
C3 O2 C2 C1 -177.16(13) . . . . ?
C4 C1 C2 O1 103.82(16) . . . . ?
C4 C1 C2 O2 -71.25(13) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C4 C9 C8 0.0(2) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C7 C8 C9 C4 -0.3(2) . . . . ?
C9 C4 C5 C6 0.2(2) . . . . ?
C10 S1 C1 O4 -72.76(10) . . . . ?
C10 S1 C1 C2 165.47(9) . . . . ?
C10 S1 C1 C4 46.43(11) . . . . ?
C10 C11 C12 C13 -1.2(4) . . . . ?
C11 C10 C15 C14 1.2(3) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C10 -1.8(3) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
C16 O4 C1 S1 -73.61(13) . . . . ?
C16 O4 C1 C2 46.28(16) . . . . ?
C16 O4 C1 C4 164.75(11) . . . . ?
C16 C17 C18 C19 179.28(19) . . . . ?
C16 C17 C22 C21 -179.2(2) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C17 C22 C21 -0.4(3) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C20 C21 C22 0.9(4) . . . . ?
C20 C21 C22 C17 -0.3(4) . . . . ?
C22 C17 C18 C19 0.6(3) . . . . ?

_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 51.088
_oxdiff_exptl_absorpt_empirical_full_min 0.493
####################################################################### 
# 
# 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_wangshch_0103
_database_code_depnum_ccdc_archive 'CCDC 2206618'
loop_
_audit_author_name
_audit_author_address
Hui
;Lanzhou University 
China
;
_audit_update_record             
;
2022-09-12 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_audit_creation_date             2020-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 N O3 S'
_chemical_formula_sum            'C21 H17 N O3 S'
_chemical_formula_weight         363.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2870(4)
_cell_length_b                   34.0526(14)
_cell_length_c                   8.7274(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3651.6(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2644
_cell_measurement_temperature    293.63(10)
_cell_measurement_theta_max      69.2410
_cell_measurement_theta_min      3.9170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7945
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         5.196
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.63(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     70.00 108.00   1.00    1.00    --  108.00-111.00  30.00   38
  2  ω     63.00 114.00   1.00    1.00    --  108.00-111.00 -90.00   51
  3  ω     94.00 133.00   1.00    1.00    --  108.00 -77.00-150.00   39
  4  ω     44.00 106.00   1.00    1.00    --   54.00-125.00 -90.00   62
  5  ω     26.00  65.00   1.00    1.00    --    0.00  57.00 150.00   39
  6  ω     98.00 160.00   1.00    1.00    --  108.00  50.00 -30.00   62
  7  ω    106.00 165.00   1.00    1.00    --  108.00 111.00 -30.00   59
  8  ω    128.00 177.00   1.00    1.00    --  108.00 111.00-150.00   49
  9  ω    100.00 129.00   1.00    1.00    --  108.00 111.00   0.00   29
 10  ω     77.00 119.00   1.00    1.00    --   54.00  57.00  30.00   42
 11  ω     36.00 101.00   1.00    1.00    --   54.00  57.00   0.00   65
 12  ω    -19.00  21.00   1.00    1.00    --    0.00 -57.00 150.00   40
 13  ω    -53.00 -26.00   1.00    1.00    --    0.00 -57.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0120184000
_diffrn_orient_matrix_UB_12      0.0308692000
_diffrn_orient_matrix_UB_13      -0.1278539000
_diffrn_orient_matrix_UB_21      0.0555316000
_diffrn_orient_matrix_UB_22      0.0308312000
_diffrn_orient_matrix_UB_23      0.1030183000
_diffrn_orient_matrix_UB_31      0.1117939000
_diffrn_orient_matrix_UB_32      -0.0119405000
_diffrn_orient_matrix_UB_33      -0.0648140000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2641
_reflns_number_total             3226
_reflns_odcompleteness_completeness 99.92
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.9545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1159
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 0.49094(4) 0.37699(2) 0.16622(7) 0.06088(19) Uani 1 1 d . . . . .
O1 O 0.63081(14) 0.46416(5) 0.14356(17) 0.0694(5) Uani 1 1 d . . . . .
O2 O 0.69971(12) 0.40694(4) 0.05882(15) 0.0548(4) Uani 1 1 d . . . . .
O3 O 0.79709(11) 0.39442(5) 0.27658(18) 0.0633(4) Uani 1 1 d . . . . .
N1 N 0.53770(17) 0.30039(6) 0.1108(2) 0.0667(5) Uani 1 1 d . . . . .
C1 C 0.65015(15) 0.45376(6) -0.1261(2) 0.0489(5) Uani 1 1 d . . . . .
C2 C 0.60680(17) 0.49025(7) -0.1655(3) 0.0582(6) Uani 1 1 d . . . . .
H2 H 0.583989 0.507512 -0.089435 0.070 Uiso 1 1 calc R U . . .
C3 C 0.5979(2) 0.50060(9) -0.3172(3) 0.0741(7) Uani 1 1 d . . . . .
H3 H 0.568488 0.524809 -0.343964 0.089 Uiso 1 1 calc R U . . .
C4 C 0.6324(2) 0.47532(9) -0.4289(3) 0.0787(8) Uani 1 1 d . . . . .
H4 H 0.625922 0.482425 -0.531351 0.094 Uiso 1 1 calc R U . . .
C5 C 0.6765(2) 0.43955(8) -0.3911(3) 0.0738(7) Uani 1 1 d . . . . .
H5 H 0.700783 0.422780 -0.467978 0.089 Uiso 1 1 calc R U . . .
C6 C 0.68489(19) 0.42845(6) -0.2399(3) 0.0594(5) Uani 1 1 d . . . . .
H6 H 0.713759 0.404062 -0.214483 0.071 Uiso 1 1 calc R U . . .
C7 C 0.65690(16) 0.44400(6) 0.0375(2) 0.0499(5) Uani 1 1 d . . . . .
C8 C 0.8713(2) 0.42456(8) 0.2333(3) 0.0784(7) Uani 1 1 d . . . . .
H8A H 0.896113 0.419954 0.130549 0.118 Uiso 1 1 calc R U . . .
H8B H 0.932384 0.424490 0.301853 0.118 Uiso 1 1 calc R U . . .
H8C H 0.835397 0.449573 0.238266 0.118 Uiso 1 1 calc R U . . .
C9 C 0.70074(17) 0.39153(6) 0.2050(2) 0.0490(5) Uani 1 1 d . . . . .
C10 C 0.61579(16) 0.37242(6) 0.2640(2) 0.0483(5) Uani 1 1 d . . . . .
C11 C 0.61818(15) 0.35225(5) 0.4144(2) 0.0475(4) Uani 1 1 d . . . . .
C12 C 0.52851(18) 0.35305(6) 0.5117(3) 0.0603(6) Uani 1 1 d . . . . .
H12 H 0.464793 0.365304 0.479685 0.072 Uiso 1 1 calc R U . . .
C13 C 0.5327(2) 0.33601(8) 0.6543(3) 0.0706(7) Uani 1 1 d . . . . .
H13 H 0.472207 0.337154 0.718230 0.085 Uiso 1 1 calc R U . . .
C14 C 0.6255(2) 0.31730(8) 0.7033(3) 0.0743(7) Uani 1 1 d . . . . .
H14 H 0.628184 0.306022 0.800245 0.089 Uiso 1 1 calc R U . . .
C15 C 0.7141(2) 0.31539(7) 0.6080(3) 0.0685(6) Uani 1 1 d . . . . .
H15 H 0.776892 0.302573 0.640229 0.082 Uiso 1 1 calc R U . . .
C16 C 0.71067(17) 0.33239(6) 0.4644(2) 0.0561(5) Uani 1 1 d . . . . .
H16 H 0.770897 0.330557 0.400252 0.067 Uiso 1 1 calc R U . . .
C17 C 0.46313(16) 0.32909(6) 0.0979(2) 0.0507(5) Uani 1 1 d . . . . .
C18 C 0.36406(18) 0.32425(8) 0.0280(3) 0.0658(6) Uani 1 1 d . . . . .
H18 H 0.314462 0.344824 0.022076 0.079 Uiso 1 1 calc R U . . .
C19 C 0.3405(2) 0.28823(11) -0.0327(3) 0.0921(9) Uani 1 1 d . . . . .
H19 H 0.273815 0.284013 -0.080363 0.111 Uiso 1 1 calc R U . . .
C20 C 0.4144(3) 0.25850(9) -0.0236(4) 0.0929(9) Uani 1 1 d . . . . .
H20 H 0.399650 0.234151 -0.067177 0.112 Uiso 1 1 calc R U . . .
C21 C 0.5095(3) 0.26504(7) 0.0498(3) 0.0807(8) Uani 1 1 d . . . . .
H21 H 0.558261 0.244293 0.059077 0.097 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.762(2) . ?
S1 C17 1.770(2) . ?
O1 C7 1.196(2) . ?
O2 C7 1.380(2) . ?
O2 C9 1.380(2) . ?
O3 C8 1.424(3) . ?
O3 C9 1.342(2) . ?
N1 C17 1.344(3) . ?
N1 C21 1.361(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.382(3) . ?
C1 C7 1.469(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(3) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.333(3) . ?
C10 C11 1.482(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.392(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.367(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.362(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.351(4) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C17 104.46(10) . . ?
C9 O2 C7 118.43(15) . . ?
C9 O3 C8 119.61(18) . . ?
C17 N1 C21 115.9(2) . . ?
C2 C1 C7 117.56(19) . . ?
C6 C1 C2 119.7(2) . . ?
C6 C1 C7 122.69(19) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
O1 C7 O2 121.51(18) . . ?
O1 C7 C1 127.41(19) . . ?
O2 C7 C1 111.08(17) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 O2 114.25(17) . . ?
C10 C9 O2 122.36(19) . . ?
C10 C9 O3 123.14(18) . . ?
C9 C10 S1 116.85(16) . . ?
C9 C10 C11 123.54(18) . . ?
C11 C10 S1 119.15(14) . . ?
C12 C11 C10 121.04(19) . . ?
C12 C11 C16 117.7(2) . . ?
C16 C11 C10 121.24(18) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
N1 C17 S1 120.67(16) . . ?
N1 C17 C18 123.7(2) . . ?
C18 C17 S1 115.59(18) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 C17 117.9(2) . . ?
C19 C18 H18 121.0 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.8(3) . . ?
C21 C20 H20 120.6 . . ?
N1 C21 H21 118.3 . . ?
C20 C21 N1 123.5(3) . . ?
C20 C21 H21 118.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C10 C11 C12 -30.1(3) . . . . ?
S1 C10 C11 C16 150.89(17) . . . . ?
S1 C17 C18 C19 177.23(19) . . . . ?
O2 C9 C10 S1 -14.1(3) . . . . ?
O2 C9 C10 C11 173.85(17) . . . . ?
O3 C9 C10 S1 172.00(16) . . . . ?
O3 C9 C10 C11 -0.1(3) . . . . ?
N1 C17 C18 C19 -0.5(3) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C7 O1 -1.3(3) . . . . ?
C2 C1 C7 O2 179.10(17) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C1 C7 O1 178.6(2) . . . . ?
C6 C1 C7 O2 -1.0(3) . . . . ?
C7 O2 C9 O3 -99.8(2) . . . . ?
C7 O2 C9 C10 85.8(2) . . . . ?
C7 C1 C2 C3 -179.5(2) . . . . ?
C7 C1 C6 C5 -179.8(2) . . . . ?
C8 O3 C9 O2 25.3(3) . . . . ?
C8 O3 C9 C10 -160.3(2) . . . . ?
C9 O2 C7 O1 7.2(3) . . . . ?
C9 O2 C7 C1 -173.13(16) . . . . ?
C9 C10 C11 C12 141.8(2) . . . . ?
C9 C10 C11 C16 -37.2(3) . . . . ?
C10 S1 C17 N1 -7.6(2) . . . . ?
C10 S1 C17 C18 174.61(16) . . . . ?
C10 C11 C12 C13 -176.7(2) . . . . ?
C10 C11 C16 C15 176.7(2) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C11 C16 C15 -2.3(3) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C11 1.0(4) . . . . ?
C16 C11 C12 C13 2.3(3) . . . . ?
C17 S1 C10 C9 114.48(17) . . . . ?
C17 S1 C10 C11 -73.07(17) . . . . ?
C17 N1 C21 C20 1.8(4) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C21 1.8(5) . . . . ?
C19 C20 C21 N1 -2.6(5) . . . . ?
C21 N1 C17 S1 -177.79(18) . . . . ?
C21 N1 C17 C18 -0.2(3) . . . . ?

_olex2_date_sample_data_collection 2020-01-03
_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.819
