# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_cr-jianxiu-g-xia-20221005
_database_code_depnum_ccdc_archive 'CCDC 2222984'
loop_
_audit_author_name
_audit_author_address
'Yanmin Guo'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Br N S'
_chemical_formula_sum            'C22 H16 Br N S'
_chemical_formula_weight         406.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   22.70389(13)
_cell_length_b                   13.29859(7)
_cell_length_c                   5.82409(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1758.467(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16569
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.0040
_cell_measurement_theta_min      3.8460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -2 4 0.1311
13 -4 0 0.0559
1 3 -4 0.1125
-13 4 0 0.0721
-11 -5 1 0.1179
-5 -5 3 0.1182
14 2 1 0.0347
-14 -2 0 0.1121
3 8 0 0.0497
-4 4 -3 0.1210
-4 -8 -1 0.0752

_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.131
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.2241 -2.3885 3.5373 -0.1218 -0.5037 0.8553
13.0576 -3.9822 0.1777 0.2007 0.8430 0.4990
0.7875 3.0882 -3.5244 0.0835 0.3426 -0.9358
-12.9965 4.0307 -0.2483 -0.1983 -0.8332 -0.5162
-11.1333 -4.5221 1.4874 0.4422 -0.8138 0.3770
-5.4217 -5.2274 2.6675 0.2974 -0.5491 0.7810
14.1921 1.8565 0.6141 -0.4577 0.8400 0.2912
-14.1792 -2.1343 -0.4340 0.4649 -0.8534 -0.2358
3.0112 8.4378 0.2028 -0.9212 0.1211 -0.3697
-3.8669 4.2517 -3.1371 -0.0142 0.0038 -0.9999
-3.6190 -8.2541 -0.6036 0.9574 -0.1256 0.2599

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            17577
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.852
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     81.00 120.00   0.50    0.05    --   83.87 125.00   0.00   78
  2  ω     90.00 119.00   0.50    0.05    --   83.87 104.00 -26.00   58
  3  ω    128.00 154.00   0.50    0.05    --   83.87 104.00 -26.00   52
  4  ω     95.00 154.00   0.50    0.05    --   83.87  38.00 -90.00  118
  5  ω    -86.00 -50.00   0.50    0.05    --  -86.37  77.00-180.00   72
  6  ω    -40.00 -15.00   0.50    0.05    --  -86.37  77.00-180.00   50
  7  ω    -40.00 -14.00   0.50    0.05    --  -86.37  38.00 -60.00   52
  8  ω    -41.00 -16.00   0.50    0.05    --  -86.37  38.00-120.00   50
  9  ω    -41.00 -16.00   0.50    0.05    --  -86.37  38.00  30.00   50
 10  ω    -41.00 -16.00   0.50    0.05    --  -86.37  38.00  60.00   50
 11  ω    -55.00 -14.00   0.50    0.05    --  -86.37  57.00 120.00   82
 12  ω    -48.00 -18.00   0.50    0.05    --  -86.37  57.00  90.00   60
 13  ω    -39.00 -14.00   0.50    0.05    --  -86.37  38.00 -90.00   50
 14  ω    -13.00  35.00   0.50    0.05    --   -1.25  57.00   0.00   96
 15  ω      1.00  69.00   0.50    0.05    --   -1.25  38.00  90.00  136
 16  ω     32.00  69.00   0.50    0.05    --   -1.25  38.00 120.00   74
 17  ω     15.00 106.00   0.50    0.05    --   83.87 -77.00 -30.00  182
 18  ω     40.00  68.00   0.50    0.05    --   83.87 -57.00-120.00   56
 19  ω     36.00  62.00   0.50    0.05    --   83.87 -57.00 -90.00   52
 20  ω     14.00  45.00   0.50    0.05    --   83.87 -57.00 -30.00   62
 21  ω     13.00  39.00   0.50    0.05    --   83.87 -38.00 120.00   52
 22  ω     18.00  66.00   0.50    0.05    --   83.87 -99.00 150.00   96
 23  ω     60.00 106.00   0.50    0.05    --   83.87-125.00 -60.00   92
 24  ω     18.00 106.00   0.50    0.05    --   83.87-125.00-150.00  176
 25  ω     59.00  84.00   0.50    0.05    --   83.87-104.00-127.00   50
 26  ω     55.00 105.00   0.50    0.05    --   83.87 -99.00  60.00  100
 27  ω     12.00  51.00   0.50    0.05    --   83.87 -99.00  60.00   78
 28  ω   -144.00 -83.00   0.50    0.05    --  -86.37 -38.00 -60.00  122
 29  ω   -132.00 -87.00   0.50    0.05    --  -86.37-104.00-127.00   90
 30  ω    -18.00  11.00   0.50    0.05    --   -1.25 -99.00-180.00   58
 31  ω    -17.00  27.00   0.50    0.05    --   -1.25 -99.00 -30.00   88
 32  ω    -98.00 -66.00   0.50    0.05    --  -86.37 104.00 -26.00   64
 33  ω   -103.00 -15.00   0.50    0.05    --  -86.37 125.00-180.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0139819000
_diffrn_orient_matrix_UB_12      -0.1014064000
_diffrn_orient_matrix_UB_13      -0.1156609000
_diffrn_orient_matrix_UB_21      0.0638438000
_diffrn_orient_matrix_UB_22      -0.0063062000
_diffrn_orient_matrix_UB_23      -0.0884592000
_diffrn_orient_matrix_UB_31      0.0182428000
_diffrn_orient_matrix_UB_32      -0.0556376000
_diffrn_orient_matrix_UB_33      0.2208418000
_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         0.690
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                3057
_reflns_number_total             3067
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1233 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0167
_refine_ls_restrained_S_all      1.068
_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)+(0.0237P)²+0.5900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0430
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
1.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
Br1 Br 0.68906(2) 0.25716(2) 0.39939(5) 0.02568(9) Uani 1 1 d . . . . .
S1 S 0.64506(2) 0.67499(4) 0.64946(8) 0.01320(12) Uani 1 1 d . . . . .
N1 N 0.66164(7) 0.73890(15) 0.2132(3) 0.0134(4) Uani 1 1 d . . . . .
C1 C 0.60394(10) 0.87904(16) 0.0967(4) 0.0168(4) Uani 1 1 d . . . . .
H1 H 0.595286 0.843132 -0.040221 0.020 Uiso 1 1 calc R U . . .
C2 C 0.58124(10) 0.97509(17) 0.1287(4) 0.0215(5) Uani 1 1 d . . . . .
H2 H 0.556509 1.004109 0.015018 0.026 Uiso 1 1 calc R U . . .
C3 C 0.59462(11) 1.02867(18) 0.3264(4) 0.0229(5) Uani 1 1 d . . . . .
H3 H 0.578607 1.093927 0.348936 0.028 Uiso 1 1 calc R U . . .
C4 C 0.63126(11) 0.98706(18) 0.4906(4) 0.0219(5) Uani 1 1 d . . . . .
H4 H 0.641202 1.024592 0.623879 0.026 Uiso 1 1 calc R U . . .
C5 C 0.65370(10) 0.89014(17) 0.4614(4) 0.0165(5) Uani 1 1 d . . . . .
H5 H 0.678657 0.861727 0.575119 0.020 Uiso 1 1 calc R U . . .
C6 C 0.63951(9) 0.83500(17) 0.2653(4) 0.0131(4) Uani 1 1 d . . . . .
C7 C 0.66492(9) 0.66645(16) 0.3571(4) 0.0120(4) Uani 1 1 d . . . . .
C8 C 0.68920(10) 0.56867(16) 0.2802(4) 0.0129(4) Uani 1 1 d . . . . .
C9 C 0.72974(9) 0.57377(16) 0.0993(4) 0.0159(4) Uani 1 1 d . . . . .
H9 H 0.740960 0.637414 0.039495 0.019 Uiso 1 1 calc R U . . .
C10 C 0.75354(11) 0.48726(18) 0.0071(4) 0.0178(5) Uani 1 1 d . . . . .
H10 H 0.780495 0.490888 -0.117395 0.021 Uiso 1 1 calc R U . . .
C11 C 0.73760(9) 0.39506(17) 0.0986(4) 0.0178(5) Uani 1 1 d . . . . .
H11 H 0.753587 0.334926 0.036360 0.021 Uiso 1 1 calc R U . . .
C12 C 0.69838(10) 0.39026(17) 0.2808(4) 0.0161(5) Uani 1 1 d . . . . .
C13 C 0.67130(9) 0.47592(16) 0.3769(4) 0.0130(4) Uani 1 1 d . . . . .
C14 C 0.62658(9) 0.47369(16) 0.5626(4) 0.0127(4) Uani 1 1 d . . . . .
C15 C 0.58742(9) 0.38310(16) 0.5927(4) 0.0132(4) Uani 1 1 d . . . . .
C16 C 0.54633(10) 0.36101(16) 0.4233(4) 0.0160(5) Uani 1 1 d . . . . .
H16 H 0.544055 0.402274 0.290438 0.019 Uiso 1 1 calc R U . . .
C17 C 0.50849(10) 0.27941(18) 0.4454(4) 0.0204(5) Uani 1 1 d . . . . .
H17 H 0.480692 0.265256 0.327834 0.025 Uiso 1 1 calc R U . . .
C18 C 0.51122(10) 0.21889(17) 0.6377(4) 0.0238(5) Uani 1 1 d . . . . .
H18 H 0.485607 0.162756 0.652243 0.029 Uiso 1 1 calc R U . . .
C19 C 0.55178(10) 0.24067(19) 0.8103(4) 0.0223(5) Uani 1 1 d . . . . .
H19 H 0.553667 0.199571 0.943490 0.027 Uiso 1 1 calc R U . . .
C20 C 0.58941(10) 0.32233(18) 0.7878(4) 0.0183(5) Uani 1 1 d . . . . .
H20 H 0.616801 0.336991 0.906490 0.022 Uiso 1 1 calc R U . . .
C21 C 0.61484(9) 0.55507(17) 0.6935(4) 0.0129(4) Uani 1 1 d . . . . .
C22 C 0.57065(9) 0.56045(16) 0.8863(4) 0.0151(4) Uani 1 1 d . . . . .
H22A H 0.585922 0.603909 1.008442 0.023 Uiso 1 1 calc R U . . .
H22B H 0.563792 0.492813 0.947526 0.023 Uiso 1 1 calc R U . . .
H22C H 0.533518 0.588110 0.828250 0.023 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
Br1 C12 1.912(2) . ?
S1 C7 1.765(2) . ?
S1 C21 1.755(2) . ?
N1 C6 1.406(3) . ?
N1 C7 1.279(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.390(3) . ?
C1 C6 1.400(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C7 C8 1.482(3) . ?
C8 C9 1.401(3) . ?
C8 C13 1.416(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C12 C13 1.410(3) . ?
C13 C14 1.484(3) . ?
C14 C15 1.507(3) . ?
C14 C21 1.350(3) . ?
C15 C16 1.389(3) . ?
C15 C20 1.395(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.508(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C21 S1 C7 100.50(10) . . ?
C7 N1 C6 124.32(18) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.3(2) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 N1 115.80(19) . . ?
C5 C6 N1 124.9(2) . . ?
C5 C6 C1 119.2(2) . . ?
N1 C7 S1 124.67(17) . . ?
N1 C7 C8 118.96(19) . . ?
C8 C7 S1 116.32(15) . . ?
C9 C8 C7 115.44(18) . . ?
C9 C8 C13 122.0(2) . . ?
C13 C8 C7 122.51(19) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.1(2) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 Br1 112.96(16) . . ?
C11 C12 C13 123.1(2) . . ?
C13 C12 Br1 123.78(17) . . ?
C8 C13 C14 120.26(19) . . ?
C12 C13 C8 114.88(19) . . ?
C12 C13 C14 124.86(19) . . ?
C13 C14 C15 120.29(18) . . ?
C21 C14 C13 122.04(19) . . ?
C21 C14 C15 117.28(19) . . ?
C16 C15 C14 118.84(19) . . ?
C16 C15 C20 118.5(2) . . ?
C20 C15 C14 122.6(2) . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.7(2) . . ?
C19 C20 H20 119.7 . . ?
C14 C21 S1 124.66(17) . . ?
C14 C21 C22 126.2(2) . . ?
C22 C21 S1 109.02(15) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 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
Br1 C12 C13 C8 173.00(16) . . . . ?
Br1 C12 C13 C14 -7.9(3) . . . . ?
S1 C7 C8 C9 -149.85(16) . . . . ?
S1 C7 C8 C13 32.2(3) . . . . ?
N1 C7 C8 C9 27.8(3) . . . . ?
N1 C7 C8 C13 -150.2(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C1 C6 N1 -178.19(19) . . . . ?
C2 C1 C6 C5 -2.5(3) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 N1 177.0(2) . . . . ?
C4 C5 C6 C1 1.7(3) . . . . ?
C6 N1 C7 S1 -2.6(3) . . . . ?
C6 N1 C7 C8 179.99(19) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C7 S1 C21 C14 21.9(2) . . . . ?
C7 S1 C21 C22 -153.55(14) . . . . ?
C7 N1 C6 C1 -139.2(2) . . . . ?
C7 N1 C6 C5 45.3(3) . . . . ?
C7 C8 C9 C10 -177.4(2) . . . . ?
C7 C8 C13 C12 179.2(2) . . . . ?
C7 C8 C13 C14 0.1(3) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C8 C13 C14 C15 151.9(2) . . . . ?
C8 C13 C14 C21 -20.8(3) . . . . ?
C9 C8 C13 C12 1.4(3) . . . . ?
C9 C8 C13 C14 -177.7(2) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 Br1 -173.91(19) . . . . ?
C10 C11 C12 C13 2.3(4) . . . . ?
C11 C12 C13 C8 -2.8(3) . . . . ?
C11 C12 C13 C14 176.3(2) . . . . ?
C12 C13 C14 C15 -27.2(3) . . . . ?
C12 C13 C14 C21 160.2(2) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
C13 C14 C15 C16 -66.9(3) . . . . ?
C13 C14 C15 C20 115.3(2) . . . . ?
C13 C14 C21 S1 5.6(3) . . . . ?
C13 C14 C21 C22 -179.68(19) . . . . ?
C14 C15 C16 C17 -178.8(2) . . . . ?
C14 C15 C20 C19 178.8(2) . . . . ?
C15 C14 C21 S1 -167.29(16) . . . . ?
C15 C14 C21 C22 7.4(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C15 C20 C19 1.0(3) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C15 -0.4(4) . . . . ?
C20 C15 C16 C17 -0.9(3) . . . . ?
C21 S1 C7 N1 143.93(19) . . . . ?
C21 S1 C7 C8 -38.61(18) . . . . ?
C21 C14 C15 C16 106.2(2) . . . . ?
C21 C14 C15 C20 -71.6(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 1.650
_oxdiff_exptl_absorpt_empirical_full_min 0.793
####################################################################### 
# 
# 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_cr-0724-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2223003'
loop_
_audit_author_name
_audit_author_address
'Yanmin Guo'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(Z)-5-chloro-3-methyl-N,4-diphenyl-1H-isothiochromen-1-imine
_chemical_formula_moiety         'C22 H16 Cl N S'
_chemical_formula_sum            'C22 H16 Cl N S'
_chemical_formula_weight         361.87
_chemical_melting_point          107.2
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Cl Cl 0.3639 0.7018 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.9095(5)
_cell_length_b                   5.86690(10)
_cell_length_c                   25.8562(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.533(2)
_cell_angle_gamma                90
_cell_volume                     3514.94(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4696
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.0900
_cell_measurement_theta_min      3.6560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.043
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 3 -9 0.1112
-11 0 -7 0.0861
-12 -2 1 0.1204
2 -3 10 0.0643
11 0 8 0.0643
-16 0 5 0.0994
3 -4 0 0.0833
10 -3 -2 0.0911
12 -1 -15 0.1263
10 3 -4 0.1363
3 3 5 0.1378
-13 0 14 0.1062
3 -3 -10 0.0784
11 3 -3 0.1367
1 0 15 0.0673
-5 -1 -13 0.0440
-2 -1 -14 0.0540
-2 -1 16 0.0650

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.146
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.3988 3.2124 -8.8966 0.1304 0.5449 0.8283
-11.0657 0.1772 -7.1490 0.2144 0.8942 -0.3930
-12.4076 -2.2333 0.6801 0.0807 0.3356 -0.9385
2.3076 -2.5530 10.4873 -0.2099 -0.8765 -0.4331
10.7226 -0.3381 7.5223 -0.2187 -0.9121 0.3467
-16.1451 -0.0032 5.2743 -0.4333 0.6302 -0.6443
3.0170 -3.7288 0.0953 0.4409 -0.6406 -0.6287
9.8619 -2.9989 -2.3520 0.5542 -0.8056 -0.2092
12.3272 -0.5294 -14.5626 0.9097 -0.1195 0.3976
9.9763 2.9954 -3.5382 -0.0502 0.0062 0.9987
3.2716 3.4317 4.7395 -0.5790 0.0757 0.8118
-12.8275 0.2166 14.3485 -0.8699 0.1143 -0.4798
2.6975 -3.0194 -10.1805 0.8660 -0.1135 -0.4871
10.5533 2.8709 -2.8746 -0.0629 -0.0671 0.9958
0.9972 -0.4332 15.1016 -0.6866 -0.7241 -0.0652
-4.8774 -0.6810 -12.7653 0.6531 0.6890 -0.3142
-2.4901 -0.5992 -14.2824 0.7446 0.6363 -0.2017
-1.8012 -0.5966 16.0067 -0.7432 -0.6354 -0.2095

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9079
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        65.823
_diffrn_reflns_theta_max         65.823
_diffrn_reflns_theta_min         3.675
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  51.00   0.50    0.05    --   90.32 -45.00  90.00   68
  2  ω     15.00  40.00   0.50    0.05    --   90.32 -45.00  30.00   50
  3  ω     22.00  49.00   0.50    0.05    --   90.32 -45.00  60.00   54
  4  ω     15.00  50.00   0.50    0.05    --   90.32 -45.00 120.00   70
  5  ω     75.00 165.00   0.50    0.05    --   90.32  53.00  22.00  180
  6  ω     37.00  67.00   0.50    0.05    --   90.32 -61.00 -90.00   60
  7  ω     18.00  49.00   0.50    0.05    --   90.32 -53.00-121.00   62
  8  ω     74.00 105.00   0.50    0.05    --   90.32 -94.00-180.00   62
  9  ω     35.00  61.00   0.50    0.05    --   90.32 -94.00-180.00   52
 10  ω   -118.00 -21.00   0.50    0.05    --  -43.34 -53.00-121.00  194
 11  ω   -117.00 -91.00   0.50    0.05    --  -43.34-125.00  30.00   52
 12  ω    -57.00  30.00   0.50    0.05    --  -43.34  53.00  22.00  174
 13  ω    -34.00  -8.00   0.50    0.05    --  -88.13  30.00  30.00   52
 14  ω    -60.00 -35.00   0.50    0.05    --  -88.13  53.00  22.00   50
 15  ω    -42.00 -11.00   0.50    0.05    --  -88.13  45.00   0.00   62
 16  ω    -51.00 -11.00   0.50    0.05    --  -88.13  45.00 -30.00   80
 17  ω    -69.00 -44.00   0.50    0.05    --  -88.13  61.00-150.00   50
 18  ω    -40.00 -15.00   0.50    0.05    --  -88.13  61.00-150.00   50
 19  ω    -46.00 -15.00   0.50    0.05    --  -88.13  45.00-180.00   62
 20  ω    -35.00 -10.00   0.50    0.05    --  -88.13  30.00-150.00   50
 21  ω    -34.00  -8.00   0.50    0.05    --  -88.13  30.00 -30.00   52
 22  ω    -35.00 -10.00   0.50    0.05    --  -88.13  30.00   0.00   50
 23  ω    -34.00  -8.00   0.50    0.05    --  -88.13  30.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0107355000
_diffrn_orient_matrix_UB_12      -0.1108040000
_diffrn_orient_matrix_UB_13      -0.0493545000
_diffrn_orient_matrix_UB_21      -0.0523904000
_diffrn_orient_matrix_UB_22      0.1283590000
_diffrn_orient_matrix_UB_23      -0.0408056000
_diffrn_orient_matrix_UB_31      0.0394826000
_diffrn_orient_matrix_UB_32      0.2005336000
_diffrn_orient_matrix_UB_33      -0.0011720000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2696
_reflns_number_total             2959
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.089
_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)+(0.0446P)²+2.5117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
1.b Idealised Me refined as rotating group:
 C1(H1C,H1A,H1B)
;
_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
Cl1 Cl 0.29089(2) 0.58844(9) 0.59541(2) 0.02822(15) Uani 1 1 d . . . . .
S1 S 0.51103(2) 0.36996(7) 0.59773(2) 0.01749(14) Uani 1 1 d . . . . .
N1 N 0.53410(6) 0.8024(2) 0.57635(6) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.49545(8) 0.1321(3) 0.67897(8) 0.0188(4) Uani 1 1 d . . . . .
H1C H 0.528648 0.190527 0.710090 0.028 Uiso 1 1 calc R U . . .
H1A H 0.508161 0.010304 0.660168 0.028 Uiso 1 1 calc R U . . .
H1B H 0.466698 0.071812 0.692997 0.028 Uiso 1 1 calc R U . . .
C2 C 0.46912(7) 0.3219(3) 0.63855(7) 0.0168(4) Uani 1 1 d . . . . .
C3 C 0.42306(7) 0.4496(3) 0.63590(7) 0.0163(4) Uani 1 1 d . . . . .
C4 C 0.39908(7) 0.4225(3) 0.68100(7) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.36925(7) 0.2281(3) 0.68646(7) 0.0200(4) Uani 1 1 d . . . . .
H5 H 0.363711 0.105404 0.661055 0.024 Uiso 1 1 calc R U . . .
C6 C 0.34764(8) 0.2130(3) 0.72871(8) 0.0244(4) Uani 1 1 d . . . . .
H6 H 0.327255 0.080219 0.731949 0.029 Uiso 1 1 calc R U . . .
C7 C 0.35562(8) 0.3911(3) 0.76644(8) 0.0257(4) Uani 1 1 d . . . . .
H7 H 0.340354 0.381158 0.795073 0.031 Uiso 1 1 calc R U . . .
C8 C 0.38602(9) 0.5828(3) 0.76182(8) 0.0263(4) Uani 1 1 d . . . . .
H8 H 0.392049 0.704191 0.787668 0.032 Uiso 1 1 calc R U . . .
C9 C 0.40770(8) 0.5982(3) 0.71960(8) 0.0215(4) Uani 1 1 d . . . . .
H9 H 0.428668 0.730076 0.716918 0.026 Uiso 1 1 calc R U . . .
C10 C 0.40120(7) 0.6337(3) 0.59434(7) 0.0162(4) Uani 1 1 d . . . . .
C11 C 0.34405(7) 0.7197(3) 0.57682(7) 0.0190(4) Uani 1 1 d . . . . .
C12 C 0.32554(8) 0.9038(3) 0.54166(8) 0.0207(4) Uani 1 1 d . . . . .
H12 H 0.287248 0.958711 0.532230 0.025 Uiso 1 1 calc R U . . .
C13 C 0.36244(8) 1.0094(3) 0.51995(7) 0.0213(4) Uani 1 1 d . . . . .
H13 H 0.349962 1.138276 0.496321 0.026 Uiso 1 1 calc R U . . .
C14 C 0.41762(8) 0.9244(3) 0.53316(7) 0.0190(4) Uani 1 1 d . . . . .
H14 H 0.442665 0.991469 0.517226 0.023 Uiso 1 1 calc R U . . .
C15 C 0.43698(7) 0.7401(3) 0.56987(7) 0.0156(4) Uani 1 1 d . . . . .
C16 C 0.49690(7) 0.6619(3) 0.58121(7) 0.0166(4) Uani 1 1 d . . . . .
C17 C 0.59187(7) 0.7371(3) 0.58712(7) 0.0167(4) Uani 1 1 d . . . . .
C18 C 0.60712(8) 0.5433(3) 0.56432(7) 0.0195(4) Uani 1 1 d . . . . .
H18 H 0.577991 0.448914 0.539543 0.023 Uiso 1 1 calc R U . . .
C19 C 0.66500(8) 0.4887(3) 0.57794(8) 0.0224(4) Uani 1 1 d . . . . .
H19 H 0.675329 0.356618 0.562437 0.027 Uiso 1 1 calc R U . . .
C20 C 0.70766(8) 0.6256(3) 0.61395(8) 0.0236(4) Uani 1 1 d . . . . .
H20 H 0.747141 0.585872 0.623839 0.028 Uiso 1 1 calc R U . . .
C21 C 0.69253(8) 0.8214(3) 0.63560(8) 0.0240(4) Uani 1 1 d . . . . .
H21 H 0.721763 0.915850 0.660240 0.029 Uiso 1 1 calc R U . . .
C22 C 0.63502(8) 0.8795(3) 0.62141(8) 0.0209(4) Uani 1 1 d . . . . .
H22 H 0.624966 1.016912 0.635098 0.025 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
Cl1 C11 1.7449(18) . ?
S1 C2 1.7583(17) . ?
S1 C16 1.7691(18) . ?
N1 C16 1.280(2) . ?
N1 C17 1.414(2) . ?
C1 H1C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 C2 1.503(2) . ?
C2 C3 1.351(2) . ?
C3 C4 1.501(2) . ?
C3 C10 1.479(2) . ?
C4 C5 1.396(3) . ?
C4 C9 1.396(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.419(2) . ?
C10 C15 1.413(2) . ?
C11 C12 1.377(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.403(2) . ?
C15 C16 1.484(2) . ?
C17 C18 1.396(3) . ?
C17 C22 1.393(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(3) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C16 101.00(8) . . ?
C16 N1 C17 121.82(15) . . ?
H1C C1 H1A 109.5 . . ?
H1C C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C1 C2 S1 109.42(12) . . ?
C3 C2 S1 124.12(14) . . ?
C3 C2 C1 126.29(16) . . ?
C2 C3 C4 118.32(15) . . ?
C2 C3 C10 121.41(16) . . ?
C10 C3 C4 119.77(15) . . ?
C5 C4 C3 122.94(16) . . ?
C9 C4 C3 118.45(16) . . ?
C9 C4 C5 118.61(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.47(17) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.45(18) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.38(18) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.25(18) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.83(17) . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C3 123.39(16) . . ?
C15 C10 C3 121.53(15) . . ?
C15 C10 C11 115.07(15) . . ?
C10 C11 Cl1 121.94(14) . . ?
C12 C11 Cl1 115.07(13) . . ?
C12 C11 C10 122.90(17) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.42(17) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.06(17) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.61(17) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C16 121.93(15) . . ?
C14 C15 C10 121.78(16) . . ?
C14 C15 C16 116.29(15) . . ?
N1 C16 S1 124.05(13) . . ?
N1 C16 C15 119.57(16) . . ?
C15 C16 S1 116.31(12) . . ?
C18 C17 N1 123.52(16) . . ?
C22 C17 N1 117.04(16) . . ?
C22 C17 C18 119.42(16) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.91(17) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.34(18) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.77(17) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.28(18) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.17(17) . . ?
C21 C22 H22 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C11 C12 C13 -174.14(15) . . . . ?
S1 C2 C3 C4 -167.09(13) . . . . ?
S1 C2 C3 C10 4.8(2) . . . . ?
N1 C17 C18 C19 -178.69(16) . . . . ?
N1 C17 C22 C21 177.33(16) . . . . ?
C1 C2 C3 C4 7.7(3) . . . . ?
C1 C2 C3 C10 179.56(16) . . . . ?
C2 S1 C16 N1 144.95(15) . . . . ?
C2 S1 C16 C15 -38.14(14) . . . . ?
C2 C3 C4 C5 -70.9(2) . . . . ?
C2 C3 C4 C9 108.27(19) . . . . ?
C2 C3 C10 C11 157.99(17) . . . . ?
C2 C3 C10 C15 -23.2(3) . . . . ?
C3 C4 C5 C6 -179.51(16) . . . . ?
C3 C4 C9 C8 179.43(16) . . . . ?
C3 C10 C11 Cl1 -9.3(2) . . . . ?
C3 C10 C11 C12 174.39(17) . . . . ?
C3 C10 C15 C14 -175.83(16) . . . . ?
C3 C10 C15 C16 4.7(3) . . . . ?
C4 C3 C10 C11 -30.2(2) . . . . ?
C4 C3 C10 C15 148.53(17) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C4 C9 C8 -1.4(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C9 C4 C5 C6 1.4(3) . . . . ?
C10 C3 C4 C5 117.12(19) . . . . ?
C10 C3 C4 C9 -63.8(2) . . . . ?
C10 C11 C12 C13 2.4(3) . . . . ?
C10 C15 C16 S1 28.6(2) . . . . ?
C10 C15 C16 N1 -154.29(17) . . . . ?
C11 C10 C15 C14 3.0(2) . . . . ?
C11 C10 C15 C16 -176.49(15) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C12 C13 C14 C15 -2.7(3) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C13 C14 C15 C16 179.94(16) . . . . ?
C14 C15 C16 S1 -150.89(13) . . . . ?
C14 C15 C16 N1 26.2(2) . . . . ?
C15 C10 C11 Cl1 171.84(13) . . . . ?
C15 C10 C11 C12 -4.4(3) . . . . ?
C16 S1 C2 C1 -152.22(12) . . . . ?
C16 S1 C2 C3 23.31(17) . . . . ?
C16 N1 C17 C18 50.1(2) . . . . ?
C16 N1 C17 C22 -131.48(18) . . . . ?
C17 N1 C16 S1 -3.7(2) . . . . ?
C17 N1 C16 C15 179.45(15) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C18 C17 C22 C21 -4.1(3) . . . . ?
C18 C19 C20 C21 -1.5(3) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C17 2.6(3) . . . . ?
C22 C17 C18 C19 2.9(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 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.850
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and n-hexane'
####################################################################### 
# 
# 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_cr-br-up-0807_auto
_database_code_depnum_ccdc_archive 'CCDC 2223000'
loop_
_audit_author_name
_audit_author_address
'Yanmin Guo'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(Z)-7-bromo-3-methyl-N,4-diphenyl-1H-isothiochromen-1-imine
_chemical_formula_moiety         'C22 H16 Br N S'
_chemical_formula_sum            'C22 H16 Br N S'
_chemical_formula_weight         406.33
_chemical_melting_point          112
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   10.2654(2)
_cell_length_b                   7.04540(10)
_cell_length_c                   12.4963(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.802(2)
_cell_angle_gamma                90
_cell_volume                     902.70(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3048
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.3480
_cell_measurement_theta_min      3.5270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.194
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.422
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -4 -1 0.0838
1 4 3 0.0711
-4 4 1 0.0742
-6 2 -2 0.0762
-3 -3 -4 0.0757
4 -4 1 0.0865
-2 4 -1 0.0612
4 4 -1 0.0826
4 -4 -1 0.0803
5 0 5 0.0983
2 3 6 0.0739
-1 4 4 0.0693
-5 3 -1 0.0778
-6 2 -3 0.0766
-3 -3 -6 0.0549
5 -3 2 0.0850
-1 -2 7 0.0449
-5 2 4 0.0878
-1 2 -7 0.0362
1 2 -7 0.0368

_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.082
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.4843 -3.8930 -0.5877 -0.0798 -0.3319 0.9399
0.6637 4.2476 2.8368 0.2037 0.8494 -0.4868
-3.5822 3.8532 0.5161 0.0755 0.3139 -0.9464
-5.7368 2.0548 -1.6061 -0.0597 -0.2502 -0.9664
-3.4973 -3.2297 -3.6283 -0.2330 -0.9724 0.0091
3.7985 -3.6967 0.9799 -0.1809 -0.1552 0.9712
-1.8704 4.3184 -1.2782 0.4052 0.3469 -0.8458
3.9853 3.6070 -1.3562 0.7575 0.6476 -0.0826
3.7525 -3.7231 -1.3812 0.0279 -0.3558 0.9342
5.3345 -0.2341 4.5211 -0.0561 0.7065 0.7055
2.1849 2.8456 5.6224 -0.0786 0.9942 -0.0730
-0.8196 3.8754 4.2270 -0.0640 0.8115 -0.5809
-5.1862 2.7527 -1.1584 0.0067 -0.0817 -0.9966
-5.5751 1.8524 -2.6640 0.0282 -0.3531 -0.9352
-2.5971 -2.6107 -5.6938 0.0789 -0.9969 -0.0082
4.6220 -3.0897 1.7620 -0.1344 0.0472 0.9898
-0.6013 -1.8562 7.4072 -0.8971 0.3171 0.3077
-5.2544 1.6217 4.3908 -0.6129 0.2170 -0.7598
-0.8126 2.4425 -6.7328 0.7929 -0.2802 -0.5412
0.6455 1.8356 -7.4206 0.8994 -0.3180 -0.3000

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4894
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        65.808
_diffrn_reflns_theta_max         65.808
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  44.00   0.50    0.08    --   90.32 -45.00-150.00   50
  2  ω     16.00  41.00   0.50    0.08    --   90.32 -45.00-180.00   50
  3  ω     32.00  79.00   0.50    0.08    --   90.32 -66.00 -13.00   94
  4  ω     14.00  49.00   0.50    0.08    --   90.32 -45.00  60.00   70
  5  ω     17.00  47.00   0.50    0.08    --   90.32 -45.00 150.00   60
  6  ω     80.00 163.00   0.50    0.08    --   90.32  66.00 121.00  166
  7  ω    -67.00  30.00   0.50    0.05    --  -43.09  66.00 121.00  194
  8  ω    -78.00 -23.00   0.50    0.08    --  -88.13  66.00 121.00  110
  9  ω    -49.00 -12.00   0.50    0.08    --  -88.13  45.00  90.00   74
 10  ω    -38.00 -11.00   0.50    0.08    --  -88.13  45.00  60.00   54
 11  ω    -39.00 -14.00   0.50    0.08    --  -88.13  45.00  30.00   50
 12  ω    -35.00 -10.00   0.50    0.08    --  -88.13  30.00  60.00   50
 13  ω    -35.00  -8.00   0.50    0.08    --  -88.13  30.00 -90.00   54
 14  ω    -40.00 -13.00   0.50    0.08    --  -88.13  45.00-120.00   54
 15  ω    -37.00 -11.00   0.50    0.08    --  -88.13  45.00-150.00   52
 16  ω    -34.00  -8.00   0.50    0.08    --  -88.13  30.00-120.00   52
 17  ω    -35.00  -8.00   0.50    0.08    --  -88.13  30.00 -60.00   54
 18  ω    -35.00 -10.00   0.50    0.08    --  -88.13  30.00  90.00   50
 19  ω    -91.00 -15.00   0.50    0.08    --  -88.13 125.00 120.00  152
 20  ω   -106.00 -20.00   0.50    0.05    --  -43.09 -66.00 -13.00  172
 21  ω   -116.00 -82.00   0.50    0.05    --  -43.09-125.00 150.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0708102000
_diffrn_orient_matrix_UB_12      0.0975998000
_diffrn_orient_matrix_UB_13      -0.0909000000
_diffrn_orient_matrix_UB_21      0.0687674000
_diffrn_orient_matrix_UB_22      0.1344117000
_diffrn_orient_matrix_UB_23      0.0820807000
_diffrn_orient_matrix_UB_31      0.1132417000
_diffrn_orient_matrix_UB_32      -0.1423633000
_diffrn_orient_matrix_UB_33      0.0150623000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1531
_reflns_number_total             1648
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1648
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.007
_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)+(0.0578P)²+0.0728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0805
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H18A(0.5) H18B(0.5) H18C(0.5)
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C16(H16), C14(H14), C3(H3), C15(H15), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
Br1 Br 0.83092(2) 0.750000 0.39683(2) 0.02227(15) Uani 1 2 d S T P . .
S1 S 0.16621(6) 0.750000 0.45618(6) 0.0207(2) Uani 1 2 d S T P . .
N1 N 0.3224(2) 0.750000 0.2949(2) 0.0232(6) Uani 1 2 d S T P . .
C7 C 0.5555(3) 0.750000 0.4128(2) 0.0177(6) Uani 1 2 d S T P . .
H7 H 0.553393 0.750000 0.336754 0.021 Uiso 1 2 calc R U P . .
C6 C 0.4390(3) 0.750000 0.4661(2) 0.0173(6) Uani 1 2 d S T P . .
C11 C 0.4409(3) 0.750000 0.5797(2) 0.0172(6) Uani 1 2 d S T P . .
C9 C 0.6789(3) 0.750000 0.5811(3) 0.0201(6) Uani 1 2 d S T P . .
H9 H 0.760758 0.750000 0.620052 0.024 Uiso 1 2 calc R U P . .
C8 C 0.6732(3) 0.750000 0.4702(2) 0.0189(6) Uani 1 2 d S T P . .
C13 C 0.3375(3) 0.750000 0.7610(2) 0.0198(6) Uani 1 2 d S T P . .
C12 C 0.3230(3) 0.750000 0.6412(2) 0.0184(6) Uani 1 2 d S T P . .
C17 C 0.2010(3) 0.750000 0.5948(2) 0.0179(6) Uani 1 2 d S T P . .
C10 C 0.5645(3) 0.750000 0.6342(2) 0.0208(6) Uani 1 2 d S T P . .
H10 H 0.568931 0.750000 0.710349 0.025 Uiso 1 2 calc R U P . .
C5 C 0.3182(3) 0.750000 0.3969(2) 0.0173(6) Uani 1 2 d S T P . .
C4 C 0.2025(3) 0.750000 0.2319(2) 0.0259(7) Uani 1 2 d S T P . .
C18 C 0.0765(3) 0.750000 0.6527(2) 0.0242(7) Uani 1 2 d S T P . .
H18A H 0.035089 0.625031 0.645629 0.036 Uiso 0.5 1 calc R U P A -1
H18B H 0.017586 0.846921 0.621603 0.036 Uiso 0.5 1 calc R U P A -1
H18C H 0.095574 0.778048 0.728650 0.036 Uiso 0.5 1 calc R U P A -1
C16 C 0.3606(3) 0.750000 0.9851(3) 0.0354(8) Uani 1 2 d S T P . .
H16 H 0.369620 0.749999 1.061103 0.043 Uiso 1 2 calc R U P . .
C14 C 0.3421(3) 0.9181(4) 0.81826(19) 0.0352(6) Uani 1 1 d . . . . .
H14 H 0.337079 1.035469 0.780868 0.042 Uiso 1 1 calc R U . . .
C3 C 0.1453(2) 0.5808(4) 0.19930(19) 0.0364(6) Uani 1 1 d . . . . .
H3 H 0.185019 0.463696 0.219974 0.044 Uiso 1 1 calc R U . . .
C15 C 0.3539(3) 0.9183(4) 0.9292(2) 0.0417(7) Uani 1 1 d . . . . .
H15 H 0.357415 1.035418 0.966922 0.050 Uiso 1 1 calc R U . . .
C1 C -0.0279(3) 0.750000 0.1055(3) 0.0484(11) Uani 1 2 d S T P . .
H1 H -0.107332 0.750001 0.063176 0.058 Uiso 1 2 calc R U P . .
C2 C 0.0295(3) 0.5813(5) 0.1361(2) 0.0477(8) Uani 1 1 d . . . . .
H2 H -0.009730 0.464600 0.114244 0.057 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
Br1 C8 1.899(3) . ?
S1 C17 1.752(3) . ?
S1 C5 1.760(3) . ?
N1 C5 1.277(4) . ?
N1 C4 1.429(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.397(4) . ?
C7 C8 1.374(4) . ?
C6 C11 1.419(4) . ?
C6 C5 1.476(4) . ?
C11 C12 1.465(4) . ?
C11 C10 1.410(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.384(5) . ?
C9 C10 1.378(4) . ?
C13 C12 1.497(4) . ?
C13 C14 1.383(3) 4_575 ?
C13 C14 1.383(3) . ?
C12 C17 1.355(4) . ?
C17 C18 1.498(4) . ?
C10 H10 0.9500 . ?
C4 C3 1.382(3) 4_575 ?
C4 C3 1.382(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C15 1.376(3) 4_575 ?
C16 C15 1.376(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.394(3) . ?
C15 H15 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.373(4) 4_575 ?
C1 C2 1.373(4) . ?
C2 H2 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 S1 C5 105.95(13) . . ?
C5 N1 C4 118.7(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.2(3) . . ?
C7 C6 C11 120.4(3) . . ?
C7 C6 C5 115.8(3) . . ?
C11 C6 C5 123.8(2) . . ?
C6 C11 C12 123.6(3) . . ?
C10 C11 C6 116.9(3) . . ?
C10 C11 C12 119.5(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C10 C9 C8 119.1(3) . . ?
C7 C8 Br1 119.8(2) . . ?
C7 C8 C9 121.0(3) . . ?
C9 C8 Br1 119.2(2) . . ?
C14 C13 C12 121.11(14) . . ?
C14 C13 C12 121.11(14) 4_575 . ?
C14 C13 C14 117.7(3) . 4_575 ?
C11 C12 C13 118.7(2) . . ?
C17 C12 C11 123.1(3) . . ?
C17 C12 C13 118.2(3) . . ?
C12 C17 S1 124.2(2) . . ?
C12 C17 C18 125.9(3) . . ?
C18 C17 S1 109.9(2) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 C11 122.3(3) . . ?
C9 C10 H10 118.8 . . ?
N1 C5 S1 119.6(2) . . ?
N1 C5 C6 121.0(2) . . ?
C6 C5 S1 119.3(2) . . ?
C3 C4 N1 120.32(15) 4_575 . ?
C3 C4 N1 120.32(15) . . ?
C3 C4 C3 119.3(3) 4_575 . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 H16 120.5 4_575 . ?
C15 C16 C15 119.0(3) . 4_575 ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C2 C1 H1 120.0 . . ?
C2 C1 H1 120.0 4_575 . ?
C2 C1 C2 119.9(3) . 4_575 ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C3 C2 -178.8(2) . . . . ?
C7 C6 C11 C12 180.000(1) . . . . ?
C7 C6 C11 C10 0.000(1) . . . . ?
C7 C6 C5 S1 180.000(0) . . . . ?
C7 C6 C5 N1 0.000(0) . . . . ?
C6 C7 C8 Br1 180.000(0) . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C6 C11 C12 C13 180.000(1) . . . . ?
C6 C11 C12 C17 0.000(1) . . . . ?
C6 C11 C10 C9 0.000(1) . . . . ?
C11 C6 C5 S1 0.000(1) . . . . ?
C11 C6 C5 N1 180.000(0) . . . . ?
C11 C12 C17 S1 0.000(1) . . . . ?
C11 C12 C17 C18 180.000(1) . . . . ?
C8 C7 C6 C11 0.000(1) . . . . ?
C8 C7 C6 C5 180.000(0) . . . . ?
C8 C9 C10 C11 0.000(1) . . . . ?
C13 C12 C17 S1 180.000(1) . . . . ?
C13 C12 C17 C18 0.000(1) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C12 C11 C10 C9 180.000(1) . . . . ?
C12 C13 C14 C15 179.2(2) . . . . ?
C17 S1 C5 N1 180.000(0) . . . . ?
C17 S1 C5 C6 0.000(0) . . . . ?
C10 C11 C12 C13 0.000(1) . . . . ?
C10 C11 C12 C17 180.000(1) . . . . ?
C10 C9 C8 Br1 180.000(1) . . . . ?
C10 C9 C8 C7 0.000(1) . . . . ?
C5 S1 C17 C12 0.000(1) . . . . ?
C5 S1 C17 C18 180.000(0) . . . . ?
C5 N1 C4 C3 -91.3(2) . . . . ?
C5 N1 C4 C3 91.3(2) . . . 4_575 ?
C5 C6 C11 C12 0.000(1) . . . . ?
C5 C6 C11 C10 180.000(1) . . . . ?
C4 N1 C5 S1 0.000(0) . . . . ?
C4 N1 C5 C6 180.000(0) . . . . ?
C4 C3 C2 C1 0.4(4) . . . . ?
C14 C13 C12 C11 -91.1(2) 4_575 . . . ?
C14 C13 C12 C11 91.1(2) . . . . ?
C14 C13 C12 C17 88.9(2) 4_575 . . . ?
C14 C13 C12 C17 -88.9(2) . . . . ?
C14 C13 C14 C15 1.4(5) 4_575 . . . ?
C3 C4 C3 C2 -1.4(5) 4_575 . . . ?
C15 C16 C15 C14 -0.7(5) 4_575 . . . ?
C2 C1 C2 C3 0.7(5) 4_575 . . . ?

_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 1.415
_oxdiff_exptl_absorpt_empirical_full_min 0.803
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and n-hexane'
####################################################################### 
# 
# 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_cr-0724-2
_database_code_depnum_ccdc_archive 'CCDC 2223004'
loop_
_audit_author_name
_audit_author_address
'Yanmin Guo'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(Z)-7-chloro-3-methyl-N,4-diphenyl-1H-isothiochromen-1-imine
_chemical_formula_moiety         'C22 H16 Cl N S'
_chemical_formula_sum            'C22 H17 Cl N S'
_chemical_formula_weight         362.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Cl Cl 0.3639 0.7018 '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'
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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   10.1263(3)
_cell_length_b                   6.9258(2)
_cell_length_c                   12.6138(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.516(3)
_cell_angle_gamma                90
_cell_volume                     883.79(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3003
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.2920
_cell_measurement_theta_min      4.3470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.026
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             378
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 0 -2 0.0470
-3 4 0 0.0466
-2 -4 3 0.0935
6 1 -4 0.0494
3 3 4 0.0520
-6 -1 2 0.0652
4 -2 -6 0.0526
6 0 -3 0.0445
1 2 7 0.0496
-6 -1 0 0.0615
-5 -2 -5 0.0716
3 -1 -7 0.0457
6 0 -5 0.0462
6 1 0 0.0513
0 3 -6 0.0592
-3 1 7 0.0528
-6 1 0 0.0512
-5 -1 5 0.0764
4 -3 4 0.0647
0 -3 -6 0.0602
5 -3 -2 0.0481

_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.103
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.3497 -0.4516 -2.3176 0.0394 0.1655 0.9854
-2.9755 4.0057 -0.0876 0.3515 -0.8474 -0.3979
-2.4471 -3.8740 2.9401 -0.3352 0.8088 -0.4832
5.8817 0.9456 -3.5513 0.0771 -0.1867 0.9794
2.6704 3.2981 4.3071 0.9546 -0.2288 0.1909
-6.3132 -0.8079 2.1016 -0.2173 0.0524 -0.9747
3.8683 -2.0229 -5.7131 -0.6015 0.1439 0.7858
6.1743 0.1733 -3.1394 0.0326 -0.0082 0.9994
1.3638 1.8179 7.2119 0.9755 0.1813 -0.1245
-6.4830 -0.7494 0.4871 -0.3701 -0.0684 -0.9265
-4.5080 -1.6972 -4.8425 -0.8932 -0.1657 -0.4180
3.2696 -1.1474 -6.9656 -0.6381 -0.1188 0.7608
5.5975 -0.2949 -4.5703 -0.1897 -0.0357 0.9812
6.4820 0.7542 -0.4655 0.3727 0.0688 0.9254
0.3831 2.8339 -6.3478 -0.2189 -0.9131 0.3439
-2.6895 1.2862 7.2384 0.7100 0.1322 -0.6917
-6.2706 1.3562 0.3138 -0.1093 -0.4571 -0.8827
-5.0427 -1.1423 5.0975 0.0848 0.3529 -0.9318
3.8236 -2.7948 4.0785 0.2189 0.9136 0.3426
0.2109 -3.2028 -5.7467 -0.9352 0.2240 0.2744
5.2619 -2.5777 -1.7385 -0.2292 0.5521 0.8017

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8365
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        65.651
_diffrn_reflns_theta_max         65.651
_diffrn_reflns_theta_min         3.507
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    110.00 137.00   0.50    0.05    --   90.32  95.00  89.00   54
  2  ω     71.00  96.00   0.50    0.05    --   90.32  61.00 -30.00   50
  3  ω    122.00 165.00   0.50    0.05    --   90.32  61.00 -30.00   86
  4  ω     49.00 117.00   0.50    0.05    --   90.32-125.00 -60.00  136
  5  ω     52.00 116.00   0.50    0.05    --   90.32-125.00-150.00  128
  6  ω    -11.00  48.00   0.50    0.05    --   45.53 -95.00 -20.00  118
  7  ω     56.00  83.00   0.50    0.05    --   90.32-125.00 150.00   54
  8  ω     89.00 116.00   0.50    0.05    --   90.32-125.00 150.00   54
  9  ω     41.00  93.00   0.50    0.05    --   90.32 -95.00 -20.00  104
 10  ω     43.00 104.00   0.50    0.05    --   90.32 -77.00 -30.00  122
 11  ω     39.00  71.00   0.50    0.05    --   90.32 -61.00-120.00   64
 12  ω     19.00  46.00   0.50    0.05    --   90.32 -45.00-150.00   54
 13  ω     28.00  60.00   0.50    0.05    --   90.32 -77.00-150.00   64
 14  ω     71.00 105.00   0.50    0.05    --   90.32 -77.00-150.00   68
 15  ω    -29.00  41.00   0.50    0.05    --   45.53 -37.00  60.00  140
 16  ω     19.00  50.00   0.50    0.05    --   90.32 -45.00 120.00   62
 17  ω   -116.00 -89.00   0.50    0.05    --  -43.34-125.00 -30.00   54
 18  ω   -139.00 -97.00   0.50    0.05    --  -88.13 -95.00 -20.00   84
 19  ω   -116.00 -59.00   0.50    0.05    --  -43.34 -77.00  30.00  114
 20  ω    -56.00 -19.00   0.50    0.05    --  -43.34 -77.00  30.00   74
 21  ω    -25.00  20.00   0.50    0.05    --  -43.34  19.00 -90.00   90
 22  ω    -43.00 -16.00   0.50    0.05    --  -88.13  61.00 -60.00   54
 23  ω    -48.00 -12.00   0.50    0.05    --  -88.13  45.00   0.00   72
 24  ω    -43.00 -14.00   0.50    0.05    --  -88.13  45.00  30.00   58
 25  ω    -48.00 -13.00   0.50    0.05    --  -88.13  45.00  60.00   70
 26  ω    -50.00 -11.00   0.50    0.05    --  -88.13  45.00  90.00   78
 27  ω    -41.00 -11.00   0.50    0.05    --  -88.13  45.00 120.00   60
 28  ω    -35.00 -10.00   0.50    0.05    --  -88.13  30.00 120.00   50
 29  ω    -34.00  -8.00   0.50    0.05    --  -88.13  30.00  90.00   52
 30  ω    -35.00 -10.00   0.50    0.05    --  -88.13  30.00 -60.00   50
 31  ω    -51.00 -11.00   0.50    0.05    --  -88.13  45.00 -60.00   80
 32  ω    -47.00 -11.00   0.50    0.05    --  -88.13  45.00-120.00   72
 33  ω    -35.00  -9.00   0.50    0.05    --  -88.13  30.00-150.00   52
 34  ω    -35.00  -8.00   0.50    0.05    --  -88.13  30.00-120.00   54
 35  ω    -35.00 -10.00   0.50    0.05    --  -88.13  30.00 -90.00   50
 36  ω    -35.00 -10.00   0.50    0.05    --  -88.13  30.00  60.00   50
 37  ω    -82.00 -54.00   0.50    0.05    --  -88.13  95.00  89.00   56
 38  ω    -88.00 -55.00   0.50    0.05    --  -88.13 125.00  90.00   66
 39  ω    -49.00 -13.00   0.50    0.05    --  -88.13 125.00  90.00   72
 40  ω    -65.00  21.00   0.50    0.05    --  -43.34  95.00  89.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0495143000
_diffrn_orient_matrix_UB_12      0.1265931000
_diffrn_orient_matrix_UB_13      0.0939919000
_diffrn_orient_matrix_UB_21      0.0365336000
_diffrn_orient_matrix_UB_22      -0.1830060000
_diffrn_orient_matrix_UB_23      0.0643551000
_diffrn_orient_matrix_UB_31      0.1392157000
_diffrn_orient_matrix_UB_32      0.0031130000
_diffrn_orient_matrix_UB_33      -0.0443814000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1488
_reflns_number_total             1643
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      0.916
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1159
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H18A(0.5) H18B(0.5) H18C(0.5)
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
Cl1 Cl 0.17380(5) 0.250000 0.59694(4) 0.0215(2) Uani 1 2 d S T P . .
S1 S 0.83470(5) 0.250000 0.54571(4) 0.0184(2) Uani 1 2 d S T P . .
N1 N 0.67457(17) 0.250000 0.70511(14) 0.0222(5) Uani 1 2 d S T P . .
C1 C 1.0257(3) 0.250000 0.8952(2) 0.0485(9) Uani 1 2 d S T P . .
H1 H 1.105649 0.250000 0.937608 0.058 Uiso 1 2 calc R U P . .
C2 C 0.9676(2) 0.4217(4) 0.86443(15) 0.0479(6) Uani 1 1 d . . . . .
H2 H 1.006865 0.540459 0.886518 0.057 Uiso 1 1 calc R U . . .
C3 C 0.85164(18) 0.4223(3) 0.80106(13) 0.0375(5) Uani 1 1 d . . . . .
H3 H 0.811824 0.541395 0.780321 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7940(2) 0.250000 0.76812(16) 0.0246(5) Uani 1 2 d S T P . .
C5 C 0.67960(19) 0.250000 0.60411(16) 0.0167(5) Uani 1 2 d S T P . .
C6 C 0.5583(2) 0.250000 0.53469(17) 0.0172(5) Uani 1 2 d S T P . .
C7 C 0.4401(2) 0.250000 0.58728(17) 0.0189(5) Uani 1 2 d S T P . .
H7 H 0.441645 0.250000 0.662643 0.023 Uiso 1 2 calc R U P . .
C8 C 0.3205(2) 0.250000 0.52999(18) 0.0183(5) Uani 1 2 d S T P . .
C9 C 0.3163(2) 0.250000 0.41997(18) 0.0193(5) Uani 1 2 d S T P . .
H9 H 0.233980 0.250000 0.380877 0.023 Uiso 1 2 calc R U P . .
C10 C 0.4333(2) 0.250000 0.36812(18) 0.0194(5) Uani 1 2 d S T P . .
H10 H 0.429840 0.250000 0.292738 0.023 Uiso 1 2 calc R U P . .
C11 C 0.5576(2) 0.250000 0.42253(16) 0.0165(5) Uani 1 2 d S T P . .
C12 C 0.6777(2) 0.250000 0.36193(16) 0.0178(5) Uani 1 2 d S T P . .
C13 C 0.6643(2) 0.250000 0.24264(17) 0.0184(5) Uani 1 2 d S T P . .
C14 C 0.6602(2) 0.0797(3) 0.18597(14) 0.0381(5) Uani 1 1 d . . . . .
H14 H 0.665290 -0.039590 0.223116 0.046 Uiso 1 1 calc R U . . .
C15 C 0.6489(2) 0.0785(3) 0.07609(15) 0.0431(5) Uani 1 1 d . . . . .
H15 H 0.645761 -0.040636 0.038769 0.052 Uiso 1 1 calc R U . . .
C16 C 0.6421(2) 0.250000 0.02109(18) 0.0301(6) Uani 1 2 d S T P . .
H16 H 0.632933 0.249999 -0.054183 0.036 Uiso 1 2 calc R U P . .
C17 C 0.8002(2) 0.250000 0.40864(16) 0.0171(5) Uani 1 2 d S T P . .
C18 C 0.9277(2) 0.250000 0.35147(17) 0.0224(5) Uani 1 2 d S T P . .
H18A H 0.968836 0.377847 0.357478 0.034 Uiso 0.5 1 calc R U P A -1
H18B H 0.909505 0.219083 0.276436 0.034 Uiso 0.5 1 calc R U P A -1
H18C H 0.987760 0.153069 0.383326 0.034 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.741(2) . ?
S1 C5 1.7638(19) . ?
S1 C17 1.749(2) . ?
N1 C4 1.418(3) . ?
N1 C5 1.277(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.375(3) 4_565 ?
C1 C2 1.375(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C5 C6 1.477(3) . ?
C6 C7 1.394(3) . ?
C6 C11 1.414(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(3) . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.407(3) . ?
C11 C12 1.465(3) . ?
C12 C13 1.505(3) . ?
C12 C17 1.349(3) . ?
C13 C14 1.379(2) . ?
C13 C14 1.379(2) 4_565 ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.507(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C17 S1 C5 105.65(10) . . ?
C5 N1 C4 119.25(17) . . ?
C2 C1 H1 120.2 4_565 . ?
C2 C1 H1 120.2 . . ?
C2 C1 C2 119.7(2) 4_565 . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 N1 120.41(11) 4_565 . ?
C3 C4 N1 120.41(11) . . ?
C3 C4 C3 119.1(2) 4_565 . ?
N1 C5 S1 119.47(16) . . ?
N1 C5 C6 121.52(17) . . ?
C6 C5 S1 119.02(15) . . ?
C7 C6 C5 115.29(19) . . ?
C7 C6 C11 120.6(2) . . ?
C11 C6 C5 124.07(18) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 Cl1 119.52(17) . . ?
C7 C8 C9 120.71(19) . . ?
C9 C8 Cl1 119.77(18) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.5(2) . . ?
C11 C10 H10 118.7 . . ?
C6 C11 C12 123.68(19) . . ?
C10 C11 C6 116.90(19) . . ?
C10 C11 C12 119.42(18) . . ?
C11 C12 C13 118.78(18) . . ?
C17 C12 C11 122.71(19) . . ?
C17 C12 C13 118.52(19) . . ?
C14 C13 C12 121.18(10) 4_565 . ?
C14 C13 C12 121.18(10) . . ?
C14 C13 C14 117.6(2) . 4_565 ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.52(17) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.97(18) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C15 119.4(2) 4_565 . ?
C15 C16 H16 120.3 4_565 . ?
C15 C16 H16 120.3 . . ?
C12 C17 S1 124.88(17) . . ?
C12 C17 C18 125.57(19) . . ?
C18 C17 S1 109.55(15) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
Cl1 C8 C9 C10 180.000(0) . . . . ?
S1 C5 C6 C7 180.000(0) . . . . ?
S1 C5 C6 C11 0.000(1) . . . . ?
N1 C5 C6 C7 0.000(1) . . . . ?
N1 C5 C6 C11 180.000(1) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C1 C2 C3 -1.0(4) 4_565 . . . ?
C2 C3 C4 N1 178.87(17) . . . . ?
C2 C3 C4 C3 1.5(3) . . . 4_565 ?
C4 N1 C5 S1 0.000(1) . . . . ?
C4 N1 C5 C6 180.000(0) . . . . ?
C5 S1 C17 C12 0.000(0) . . . . ?
C5 S1 C17 C18 180.000(0) . . . . ?
C5 N1 C4 C3 91.32(17) . . . . ?
C5 N1 C4 C3 -91.32(17) . . . 4_565 ?
C5 C6 C7 C8 180.000(0) . . . . ?
C5 C6 C11 C10 180.000(0) . . . . ?
C5 C6 C11 C12 0.000(1) . . . . ?
C6 C7 C8 Cl1 180.000(0) . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C6 C11 C12 C13 180.000(0) . . . . ?
C6 C11 C12 C17 0.000(0) . . . . ?
C7 C6 C11 C10 0.000(0) . . . . ?
C7 C6 C11 C12 180.000(0) . . . . ?
C7 C8 C9 C10 0.000(1) . . . . ?
C8 C9 C10 C11 0.000(0) . . . . ?
C9 C10 C11 C6 0.000(0) . . . . ?
C9 C10 C11 C12 180.000(0) . . . . ?
C10 C11 C12 C13 0.000(0) . . . . ?
C10 C11 C12 C17 180.000(0) . . . . ?
C11 C6 C7 C8 0.000(1) . . . . ?
C11 C12 C13 C14 91.11(19) . . . 4_565 ?
C11 C12 C13 C14 -91.11(19) . . . . ?
C11 C12 C17 S1 0.000(0) . . . . ?
C11 C12 C17 C18 180.000(0) . . . . ?
C12 C13 C14 C15 -179.52(18) . . . . ?
C13 C12 C17 S1 180.000(0) . . . . ?
C13 C12 C17 C18 0.000(0) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C13 C14 C15 -1.7(4) 4_565 . . . ?
C14 C15 C16 C15 1.0(4) . . . 4_565 ?
C17 S1 C5 N1 180.000(0) . . . . ?
C17 S1 C5 C6 0.000(0) . . . . ?
C17 C12 C13 C14 88.89(19) . . . . ?
C17 C12 C13 C14 -88.89(19) . . . 4_565 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.478
_oxdiff_exptl_absorpt_empirical_full_min 0.883
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and n-hexane'
####################################################################### 
# 
# 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_cr-ea-hex_auto
_database_code_depnum_ccdc_archive 'CCDC 2223005'
loop_
_audit_author_name
_audit_author_address
'Yanmin Guo'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(Z)-5-(tert-butyl)-3-methyl-N,4-diphenyl-1H-isothiochromen-1-imine
_chemical_formula_moiety         'C26 H25 N S'
_chemical_formula_sum            'C26 H25 N S'
_chemical_formula_weight         383.53
_chemical_melting_point          128.8
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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                   11.3822(2)
_cell_length_b                   12.2394(3)
_cell_length_c                   16.8294(4)
_cell_angle_alpha                74.050(2)
_cell_angle_beta                 80.114(2)
_cell_angle_gamma                67.955(2)
_cell_volume                     2083.27(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15014
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      66.6870
_cell_measurement_theta_min      2.7250
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.742
_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -3 1 0.1071
0 6 -4 0.0449
0 -6 4 0.0648
-7 -3 0 0.1129
0 0 -10 0.0417
7 3 -3 0.0810
1 0 10 0.0172
-7 -3 -4 0.1243
0 -1 -11 0.0440
7 3 -2 0.0845
1 2 11 0.0247

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.066
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.0458 -3.1825 1.2118 -0.0159 -0.0593 0.9981
0.0823 6.1051 -3.8591 0.2299 0.9606 -0.1565
0.0348 -6.0733 3.8523 -0.2304 -0.9629 0.1404
-7.2830 -2.8717 -0.0665 -0.0669 0.0756 0.9949
-0.2358 0.2325 -10.4063 -0.6316 0.7387 -0.2352
6.6191 2.7045 -2.9612 -0.1220 0.1451 -0.9819
0.7027 -0.0506 10.4801 0.6401 -0.7485 0.1732
-7.2381 -3.4272 -3.9819 -0.3575 0.2718 0.8935
0.0149 -1.1514 -10.7282 -0.7650 0.5864 -0.2662
6.9111 2.6474 -1.9906 -0.0718 0.0572 -0.9958
1.0573 1.6134 10.8943 0.7877 -0.6035 0.1234

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21719
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         2.739
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    104.00 155.00   0.50    0.13    --   83.87  77.00 -30.00  102
  2  ω    122.00 156.00   0.50    0.13    --   83.87 125.00  30.00   68
  3  ω     80.00 105.00   0.50    0.13    --   83.87 125.00  30.00   50
  4  ω     66.00  93.00   0.50    0.13    --   83.87  77.00 -30.00   54
  5  ω    121.00 153.00   0.50    0.13    --   83.87 104.00-176.00   64
  6  ω    -41.00 -16.00   0.50    0.13    --  -86.37  38.00 150.00   50
  7  ω    -46.00 -14.00   0.50    0.13    --  -86.37  77.00 150.00   64
  8  ω    -97.00 -59.00   0.50    0.13    --  -86.37  77.00 150.00   76
  9  ω    -40.00 -15.00   0.50    0.13    --  -86.37  38.00 120.00   50
 10  ω    -77.00 -39.00   0.50    0.13    --  -86.37  77.00  60.00   76
 11  ω   -103.00 -77.00   0.50    0.13    --  -86.37  77.00   0.00   52
 12  ω    -46.00 -14.00   0.50    0.13    --  -86.37  77.00   0.00   64
 13  ω     26.00  64.00   0.50    0.05    --   -1.25  38.00 -30.00   76
 14  ω    -66.00 -15.00   0.50    0.13    --  -86.37 125.00  30.00  102
 15  ω   -105.00 -72.00   0.50    0.13    --  -86.37 125.00  30.00   66
 16  ω   -108.00 -14.00   0.50    0.13    --  -86.37 125.00-180.00  188
 17  ω    -96.00 -49.00   0.50    0.13    --  -86.37 104.00-176.00   94
 18  ω    -73.00   9.00   0.50    0.05    --   -1.25 -57.00  30.00  164
 19  ω    -16.00  16.00   0.50    0.05    --   -1.25 -99.00 -90.00   64
 20  ω    -16.00  31.00   0.50    0.05    --   -1.25 -99.00 -60.00   94
 21  ω    -18.00   7.00   0.50    0.05    --   -1.25 -99.00   0.00   50
 22  ω   -156.00 -67.00   0.50    0.13    --  -86.37 -77.00 -30.00  178
 23  ω   -129.00 -87.00   0.50    0.13    --  -86.37-104.00  82.00   84
 24  ω    -17.00  28.00   0.50    0.05    --   -1.25 -99.00 120.00   90
 25  ω     58.00 106.00   0.50    0.13    --   83.87-125.00  30.00   96
 26  ω     67.00 106.00   0.50    0.13    --   83.87-104.00  82.00   78
 27  ω     12.00  62.00   0.50    0.13    --   83.87 -57.00 150.00  100
 28  ω     20.00  58.00   0.50    0.13    --   83.87 -57.00 120.00   76
 29  ω     12.00  40.00   0.50    0.13    --   83.87 -57.00  90.00   56
 30  ω     12.00  44.00   0.50    0.13    --   83.87 -38.00   0.00   64
 31  ω     12.00  45.00   0.50    0.13    --   83.87 -38.00 -30.00   66
 32  ω     13.00  45.00   0.50    0.13    --   83.87 -38.00 -60.00   64
 33  ω     12.00  45.00   0.50    0.13    --   83.87 -38.00 -90.00   66
 34  ω     15.00  44.00   0.50    0.13    --   83.87 -38.00-120.00   58
 35  ω     14.00 105.00   0.50    0.13    --   83.87 -99.00 -90.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0220364000
_diffrn_orient_matrix_UB_12      0.0777328000
_diffrn_orient_matrix_UB_13      0.0629341000
_diffrn_orient_matrix_UB_21      -0.0553624000
_diffrn_orient_matrix_UB_22      0.1156376000
_diffrn_orient_matrix_UB_23      -0.0671491000
_diffrn_orient_matrix_UB_31      -0.1337889000
_diffrn_orient_matrix_UB_32      -0.0077318000
_diffrn_orient_matrix_UB_33      0.0254610000
_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                6395
_reflns_number_total             7193
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7193
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.045
_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)+(0.1228P)²+1.3118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1765
_refine_ls_wR_factor_ref         0.1816
_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. Uiso/Uaniso restraints and constraints
Uanis(S1) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C7) = Uanis(S1)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C15(H15), C16(H16), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31), C35(H35), C41(H41), C42(H42), C46(H46), C47(H47), C48(H48),
 C49(H49), C50(H50)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C26(H26A,H26B,
 H26C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C52(H52A,
 H52B,H52C)
;
_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 0.25105(5) 0.89103(5) 0.30772(4) 0.02655(18) Uani 1 1 d . U . . .
N1 N 0.13448(19) 0.83681(18) 0.20726(13) 0.0289(5) Uani 1 1 d . . . . .
C1 C 0.3534(2) 0.7118(2) 0.17538(16) 0.0298(5) Uani 1 1 d . . . . .
H1 H 0.373578 0.781954 0.147056 0.036 Uiso 1 1 calc R U . . .
C2 C 0.4427(2) 0.5982(2) 0.17622(15) 0.0298(5) Uani 1 1 d . . . . .
H2 H 0.523891 0.590511 0.147567 0.036 Uiso 1 1 calc R U . . .
C3 C 0.4153(2) 0.4946(2) 0.21851(16) 0.0326(6) Uani 1 1 d . . . . .
H3 H 0.476970 0.416542 0.218368 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2971(2) 0.5066(2) 0.26085(17) 0.0344(6) Uani 1 1 d . . . . .
H4 H 0.278351 0.436516 0.291315 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2064(2) 0.6202(2) 0.25887(16) 0.0314(6) Uani 1 1 d . . . . .
H5 H 0.124856 0.627850 0.286947 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2339(2) 0.7234(2) 0.21602(15) 0.0264(5) Uani 1 1 d . . . . .
C7 C 0.1318(2) 0.9176(2) 0.24322(15) 0.02655(18) Uani 1 1 d . U . . .
C8 C 0.0268(2) 1.0363(2) 0.22974(14) 0.0234(5) Uani 1 1 d . . . . .
C9 C -0.0455(2) 1.0641(2) 0.16233(14) 0.0241(5) Uani 1 1 d . . . . .
H9 H -0.024771 1.006745 0.129301 0.029 Uiso 1 1 calc R U . . .
C10 C -0.1462(2) 1.1724(2) 0.14227(14) 0.0238(5) Uani 1 1 d . . . . .
C11 C -0.2140(2) 1.2083(2) 0.06318(14) 0.0242(5) Uani 1 1 d . . . . .
C12 C -0.2274(3) 1.0973(3) 0.04481(19) 0.0450(7) Uani 1 1 d . . . . .
H12A H -0.272936 1.122638 -0.005244 0.067 Uiso 1 1 calc R U . . .
H12B H -0.274978 1.060566 0.091752 0.067 Uiso 1 1 calc R U . . .
H12C H -0.142761 1.038032 0.036233 0.067 Uiso 1 1 calc R U . . .
C13 C -0.3478(3) 1.3013(3) 0.06962(19) 0.0466(8) Uani 1 1 d . . . . .
H13A H -0.342273 1.376888 0.075145 0.070 Uiso 1 1 calc R U . . .
H13B H -0.396674 1.269773 0.118269 0.070 Uiso 1 1 calc R U . . .
H13C H -0.390174 1.317010 0.019567 0.070 Uiso 1 1 calc R U . . .
C14 C -0.1372(3) 1.2637(3) -0.00825(16) 0.0416(7) Uani 1 1 d . . . . .
H14A H -0.051691 1.204376 -0.014287 0.062 Uiso 1 1 calc R U . . .
H14B H -0.131081 1.335707 0.002985 0.062 Uiso 1 1 calc R U . . .
H14C H -0.179200 1.286601 -0.059540 0.062 Uiso 1 1 calc R U . . .
C15 C -0.1772(2) 1.2504(2) 0.19579(15) 0.0269(5) Uani 1 1 d . . . . .
H15 H -0.248309 1.323351 0.186065 0.032 Uiso 1 1 calc R U . . .
C16 C -0.1070(2) 1.2243(2) 0.26270(15) 0.0276(5) Uani 1 1 d . . . . .
H16 H -0.131855 1.279916 0.297437 0.033 Uiso 1 1 calc R U . . .
C17 C 0.0002(2) 1.1179(2) 0.28083(14) 0.0242(5) Uani 1 1 d . . . . .
C18 C 0.0784(2) 1.1008(2) 0.34602(14) 0.0262(5) Uani 1 1 d . . . . .
C19 C 0.0352(2) 1.1970(2) 0.39471(14) 0.0265(5) Uani 1 1 d . . . . .
C20 C -0.0530(2) 1.1946(2) 0.46327(15) 0.0295(5) Uani 1 1 d . . . . .
H20 H -0.081586 1.127563 0.482619 0.035 Uiso 1 1 calc R U . . .
C21 C -0.0992(2) 1.2885(2) 0.50324(16) 0.0329(6) Uani 1 1 d . . . . .
H21 H -0.158139 1.285061 0.550427 0.040 Uiso 1 1 calc R U . . .
C22 C -0.0601(3) 1.3874(2) 0.47501(16) 0.0351(6) Uani 1 1 d . . . . .
H22 H -0.094237 1.453415 0.501398 0.042 Uiso 1 1 calc R U . . .
C23 C 0.0292(3) 1.3899(3) 0.40800(18) 0.0415(7) Uani 1 1 d . . . . .
H23 H 0.057772 1.456979 0.389158 0.050 Uiso 1 1 calc R U . . .
C24 C 0.0766(3) 1.2960(2) 0.36872(16) 0.0331(6) Uani 1 1 d . . . . .
H24 H 0.138538 1.298354 0.323175 0.040 Uiso 1 1 calc R U . . .
C25 C 0.1869(2) 1.0123(2) 0.36002(12) 0.0186(5) Uani 1 1 d . . . . .
C26 C 0.2782(2) 0.9914(2) 0.42358(15) 0.0311(6) Uani 1 1 d . . . . .
H26A H 0.298100 0.908587 0.457682 0.047 Uiso 1 1 calc R U . . .
H26B H 0.238552 1.049148 0.459075 0.047 Uiso 1 1 calc R U . . .
H26C H 0.356658 1.002962 0.394860 0.047 Uiso 1 1 calc R U . . .
S2 S -0.32673(6) 1.02930(5) 0.35929(4) 0.02679(18) Uani 1 1 d . . . . .
N2 N -0.54891(19) 1.20834(18) 0.33330(12) 0.0257(4) Uani 1 1 d . . . . .
C27 C -0.6112(3) 1.2587(3) 0.46636(16) 0.0350(6) Uani 1 1 d . . . . .
H27 H -0.680223 1.230864 0.471703 0.042 Uiso 1 1 calc R U . . .
C28 C -0.5972(3) 1.3078(3) 0.52730(17) 0.0395(7) Uani 1 1 d . . . . .
H28 H -0.656714 1.313158 0.574423 0.047 Uiso 1 1 calc R U . . .
C29 C -0.4968(3) 1.3494(2) 0.52045(16) 0.0356(6) Uani 1 1 d . . . . .
H29 H -0.486389 1.381657 0.563017 0.043 Uiso 1 1 calc R U . . .
C30 C -0.4120(2) 1.3431(2) 0.45034(17) 0.0322(6) Uani 1 1 d . . . . .
H30 H -0.344724 1.373550 0.444123 0.039 Uiso 1 1 calc R U . . .
C31 C -0.4250(2) 1.2926(2) 0.38940(16) 0.0282(5) Uani 1 1 d . . . . .
H31 H -0.365602 1.287209 0.342238 0.034 Uiso 1 1 calc R U . . .
C32 C -0.5246(2) 1.2499(2) 0.39710(14) 0.0254(5) Uani 1 1 d . . . . .
C33 C -0.4692(2) 1.1144(2) 0.31012(14) 0.0238(5) Uani 1 1 d . . . . .
C34 C -0.4951(2) 1.0756(2) 0.24069(13) 0.0212(5) Uani 1 1 d . . . . .
C35 C -0.5952(2) 1.1599(2) 0.19353(14) 0.0241(5) Uani 1 1 d . . . . .
H35 H -0.641008 1.235153 0.208296 0.029 Uiso 1 1 calc R U . . .
C36 C -0.6298(2) 1.1372(2) 0.12610(14) 0.0235(5) Uani 1 1 d . . . . .
C37 C -0.7289(2) 1.2333(2) 0.06932(14) 0.0233(5) Uani 1 1 d . . . . .
C38 C -0.8332(3) 1.3179(3) 0.11716(17) 0.0419(7) Uani 1 1 d . . . . .
H38A H -0.898557 1.374502 0.079976 0.063 Uiso 1 1 calc R U . . .
H38B H -0.796316 1.363313 0.138969 0.063 Uiso 1 1 calc R U . . .
H38C H -0.871483 1.269980 0.163208 0.063 Uiso 1 1 calc R U . . .
C39 C -0.7924(3) 1.1756(3) 0.02697(17) 0.0366(6) Uani 1 1 d . . . . .
H39A H -0.729106 1.130114 -0.010394 0.055 Uiso 1 1 calc R U . . .
H39B H -0.860847 1.239394 -0.004862 0.055 Uiso 1 1 calc R U . . .
H39C H -0.827641 1.120683 0.069179 0.055 Uiso 1 1 calc R U . . .
C40 C -0.6611(2) 1.3061(2) 0.00182(16) 0.0333(6) Uani 1 1 d . . . . .
H40A H -0.628587 1.351477 0.026893 0.050 Uiso 1 1 calc R U . . .
H40B H -0.721166 1.362766 -0.038860 0.050 Uiso 1 1 calc R U . . .
H40C H -0.590245 1.250784 -0.025835 0.050 Uiso 1 1 calc R U . . .
C41 C -0.5620(2) 1.0226(2) 0.10909(14) 0.0252(5) Uani 1 1 d . . . . .
H41 H -0.584796 1.002257 0.064779 0.030 Uiso 1 1 calc R U . . .
C42 C -0.4634(2) 0.9389(2) 0.15498(14) 0.0247(5) Uani 1 1 d . . . . .
H42 H -0.420166 0.862640 0.141095 0.030 Uiso 1 1 calc R U . . .
C43 C -0.4244(2) 0.9627(2) 0.22211(14) 0.0231(5) Uani 1 1 d . . . . .
C44 C -0.3137(2) 0.8750(2) 0.26369(14) 0.0231(5) Uani 1 1 d . . . . .
C45 C -0.2500(2) 0.7560(2) 0.23972(14) 0.0245(5) Uani 1 1 d . . . . .
C46 C -0.3102(2) 0.6700(2) 0.25828(14) 0.0245(5) Uani 1 1 d . . . . .
H46 H -0.393859 0.688507 0.284513 0.029 Uiso 1 1 calc R U . . .
C47 C -0.2494(2) 0.5592(2) 0.23893(15) 0.0286(5) Uani 1 1 d . . . . .
H47 H -0.290843 0.501241 0.252764 0.034 Uiso 1 1 calc R U . . .
C48 C -0.1275(2) 0.5309(2) 0.19924(15) 0.0289(5) Uani 1 1 d . . . . .
H48 H -0.085982 0.454365 0.185571 0.035 Uiso 1 1 calc R U . . .
C49 C -0.0675(2) 0.6156(2) 0.17990(14) 0.0252(5) Uani 1 1 d . . . . .
H49 H 0.015882 0.596950 0.153170 0.030 Uiso 1 1 calc R U . . .
C50 C -0.1286(2) 0.7277(2) 0.19937(14) 0.0257(5) Uani 1 1 d . . . . .
H50 H -0.087135 0.785717 0.185036 0.031 Uiso 1 1 calc R U . . .
C51 C -0.26314(19) 0.89825(18) 0.31982(13) 0.0171(4) Uani 1 1 d . . . . .
C52 C -0.1450(2) 0.8133(2) 0.36521(15) 0.0284(5) Uani 1 1 d . . . . .
H52A H -0.070581 0.833476 0.336704 0.043 Uiso 1 1 calc R U . . .
H52B H -0.132029 0.729366 0.365681 0.043 Uiso 1 1 calc R U . . .
H52C H -0.156679 0.822795 0.422314 0.043 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 C7 1.762(2) . ?
S1 C25 1.787(2) . ?
N1 C6 1.412(3) . ?
N1 C7 1.283(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(4) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(4) . ?
C7 C8 1.483(3) . ?
C8 C9 1.407(3) . ?
C8 C17 1.408(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(3) . ?
C10 C11 1.529(3) . ?
C10 C15 1.399(3) . ?
C11 C12 1.538(4) . ?
C11 C13 1.528(4) . ?
C11 C14 1.518(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.412(3) . ?
C17 C18 1.452(3) . ?
C18 C19 1.503(3) . ?
C18 C25 1.307(3) . ?
C19 C20 1.395(3) . ?
C19 C24 1.397(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.370(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.523(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
S2 C33 1.766(2) . ?
S2 C51 1.757(2) . ?
N2 C32 1.413(3) . ?
N2 C33 1.280(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.379(4) . ?
C27 C32 1.391(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.393(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.390(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.390(3) . ?
C33 C34 1.485(3) . ?
C34 C35 1.405(3) . ?
C34 C43 1.403(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.388(3) . ?
C36 C37 1.525(3) . ?
C36 C41 1.406(3) . ?
C37 C38 1.529(3) . ?
C37 C39 1.538(3) . ?
C37 C40 1.529(3) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41 0.9500 . ?
C41 C42 1.381(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.418(3) . ?
C43 C44 1.450(3) . ?
C44 C45 1.496(3) . ?
C44 C51 1.328(3) . ?
C45 C46 1.400(3) . ?
C45 C50 1.393(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.373(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.392(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.385(3) . ?
C49 H49 0.9500 . ?
C49 C50 1.388(3) . ?
C50 H50 0.9500 . ?
C51 C52 1.529(3) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?

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
C7 S1 C25 103.96(11) . . ?
C7 N1 C6 121.8(2) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.8(2) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 N1 121.5(2) . . ?
C1 C6 C5 119.6(2) . . ?
C5 C6 N1 118.5(2) . . ?
N1 C7 S1 121.40(19) . . ?
N1 C7 C8 119.3(2) . . ?
C8 C7 S1 119.27(17) . . ?
C9 C8 C7 116.3(2) . . ?
C9 C8 C17 121.2(2) . . ?
C17 C8 C7 122.4(2) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.4(2) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C11 122.0(2) . . ?
C9 C10 C15 116.3(2) . . ?
C15 C10 C11 121.6(2) . . ?
C10 C11 C12 110.8(2) . . ?
C13 C11 C10 112.1(2) . . ?
C13 C11 C12 107.2(2) . . ?
C14 C11 C10 108.53(19) . . ?
C14 C11 C12 109.8(2) . . ?
C14 C11 C13 108.3(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15 119.0 . . ?
C16 C15 C10 122.0(2) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 118.9 . . ?
C15 C16 C17 122.2(2) . . ?
C17 C16 H16 118.9 . . ?
C8 C17 C16 115.7(2) . . ?
C8 C17 C18 124.1(2) . . ?
C16 C17 C18 120.1(2) . . ?
C17 C18 C19 116.9(2) . . ?
C25 C18 C17 123.7(2) . . ?
C25 C18 C19 119.2(2) . . ?
C20 C19 C18 121.5(2) . . ?
C20 C19 C24 118.1(2) . . ?
C24 C19 C18 120.2(2) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.9(2) . . ?
C23 C24 H24 119.6 . . ?
C18 C25 S1 124.56(17) . . ?
C18 C25 C26 127.3(2) . . ?
C26 C25 S1 108.17(17) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C51 S2 C33 104.54(10) . . ?
C33 N2 C32 121.5(2) . . ?
C28 C27 H27 119.8 . . ?
C28 C27 C32 120.3(2) . . ?
C32 C27 H27 119.8 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.7(3) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 120.5 . . ?
C30 C29 C28 119.0(2) . . ?
C30 C29 H29 120.5 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.5(2) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.2(2) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 N2 118.1(2) . . ?
C31 C32 N2 122.3(2) . . ?
C31 C32 C27 119.3(2) . . ?
N2 C33 S2 120.92(18) . . ?
N2 C33 C34 120.3(2) . . ?
C34 C33 S2 118.80(17) . . ?
C35 C34 C33 115.6(2) . . ?
C43 C34 C33 122.9(2) . . ?
C43 C34 C35 121.4(2) . . ?
C34 C35 H35 118.8 . . ?
C36 C35 C34 122.3(2) . . ?
C36 C35 H35 118.8 . . ?
C35 C36 C37 122.4(2) . . ?
C35 C36 C41 116.4(2) . . ?
C41 C36 C37 121.1(2) . . ?
C36 C37 C38 111.44(19) . . ?
C36 C37 C39 111.5(2) . . ?
C36 C37 C40 107.96(18) . . ?
C38 C37 C39 108.0(2) . . ?
C38 C37 C40 109.8(2) . . ?
C40 C37 C39 108.1(2) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C36 C41 H41 119.1 . . ?
C42 C41 C36 121.9(2) . . ?
C42 C41 H41 119.1 . . ?
C41 C42 H42 118.9 . . ?
C41 C42 C43 122.2(2) . . ?
C43 C42 H42 118.9 . . ?
C34 C43 C42 115.7(2) . . ?
C34 C43 C44 124.6(2) . . ?
C42 C43 C44 119.6(2) . . ?
C43 C44 C45 119.0(2) . . ?
C51 C44 C43 122.4(2) . . ?
C51 C44 C45 118.5(2) . . ?
C46 C45 C44 120.9(2) . . ?
C50 C45 C44 120.6(2) . . ?
C50 C45 C46 118.5(2) . . ?
C45 C46 H46 119.7 . . ?
C47 C46 C45 120.7(2) . . ?
C47 C46 H46 119.7 . . ?
C46 C47 H47 119.7 . . ?
C46 C47 C48 120.6(2) . . ?
C48 C47 H47 119.7 . . ?
C47 C48 H48 120.4 . . ?
C49 C48 C47 119.2(2) . . ?
C49 C48 H48 120.4 . . ?
C48 C49 H49 119.8 . . ?
C48 C49 C50 120.3(2) . . ?
C50 C49 H49 119.8 . . ?
C45 C50 H50 119.7 . . ?
C49 C50 C45 120.6(2) . . ?
C49 C50 H50 119.7 . . ?
C44 C51 S2 125.47(17) . . ?
C44 C51 C52 126.3(2) . . ?
C52 C51 S2 108.12(15) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 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 C7 C8 C9 163.94(17) . . . . ?
S1 C7 C8 C17 -15.7(3) . . . . ?
N1 C7 C8 C9 -15.6(3) . . . . ?
N1 C7 C8 C17 164.7(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C1 C6 N1 -171.2(2) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 N1 172.6(2) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C6 N1 C7 S1 -1.2(3) . . . . ?
C6 N1 C7 C8 178.3(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C7 S1 C25 C18 -3.5(2) . . . . ?
C7 S1 C25 C26 174.96(15) . . . . ?
C7 N1 C6 C1 -74.9(3) . . . . ?
C7 N1 C6 C5 112.4(3) . . . . ?
C7 C8 C9 C10 -179.6(2) . . . . ?
C7 C8 C17 C16 -176.8(2) . . . . ?
C7 C8 C17 C18 6.2(3) . . . . ?
C8 C9 C10 C11 172.6(2) . . . . ?
C8 C9 C10 C15 -3.5(3) . . . . ?
C8 C17 C18 C19 -179.7(2) . . . . ?
C8 C17 C18 C25 5.3(4) . . . . ?
C9 C8 C17 C16 3.5(3) . . . . ?
C9 C8 C17 C18 -173.5(2) . . . . ?
C9 C10 C11 C12 38.2(3) . . . . ?
C9 C10 C11 C13 158.0(2) . . . . ?
C9 C10 C11 C14 -82.4(3) . . . . ?
C9 C10 C15 C16 3.4(3) . . . . ?
C10 C15 C16 C17 0.2(4) . . . . ?
C11 C10 C15 C16 -172.7(2) . . . . ?
C15 C10 C11 C12 -145.9(2) . . . . ?
C15 C10 C11 C13 -26.1(3) . . . . ?
C15 C10 C11 C14 93.6(3) . . . . ?
C15 C16 C17 C8 -3.7(3) . . . . ?
C15 C16 C17 C18 173.4(2) . . . . ?
C16 C17 C18 C19 3.4(3) . . . . ?
C16 C17 C18 C25 -171.6(2) . . . . ?
C17 C8 C9 C10 0.0(3) . . . . ?
C17 C18 C19 C20 85.6(3) . . . . ?
C17 C18 C19 C24 -90.2(3) . . . . ?
C17 C18 C25 S1 -5.4(3) . . . . ?
C17 C18 C25 C26 176.4(2) . . . . ?
C18 C19 C20 C21 -174.8(2) . . . . ?
C18 C19 C24 C23 174.0(3) . . . . ?
C19 C18 C25 S1 179.74(16) . . . . ?
C19 C18 C25 C26 1.6(4) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
C20 C19 C24 C23 -1.9(4) . . . . ?
C20 C21 C22 C23 -2.3(4) . . . . ?
C21 C22 C23 C24 1.4(4) . . . . ?
C22 C23 C24 C19 0.7(4) . . . . ?
C24 C19 C20 C21 1.0(4) . . . . ?
C25 S1 C7 N1 -167.2(2) . . . . ?
C25 S1 C7 C8 13.3(2) . . . . ?
C25 C18 C19 C20 -99.3(3) . . . . ?
C25 C18 C19 C24 85.0(3) . . . . ?
S2 C33 C34 C35 -167.23(16) . . . . ?
S2 C33 C34 C43 12.3(3) . . . . ?
N2 C33 C34 C35 12.4(3) . . . . ?
N2 C33 C34 C43 -168.1(2) . . . . ?
C27 C28 C29 C30 1.3(4) . . . . ?
C28 C27 C32 N2 -174.9(2) . . . . ?
C28 C27 C32 C31 -0.9(4) . . . . ?
C28 C29 C30 C31 -2.0(4) . . . . ?
C29 C30 C31 C32 1.3(4) . . . . ?
C30 C31 C32 N2 173.9(2) . . . . ?
C30 C31 C32 C27 0.2(4) . . . . ?
C32 N2 C33 S2 2.0(3) . . . . ?
C32 N2 C33 C34 -177.6(2) . . . . ?
C32 C27 C28 C29 0.2(4) . . . . ?
C33 S2 C51 C44 1.6(2) . . . . ?
C33 S2 C51 C52 -174.89(15) . . . . ?
C33 N2 C32 C27 -121.7(3) . . . . ?
C33 N2 C32 C31 64.5(3) . . . . ?
C33 C34 C35 C36 179.3(2) . . . . ?
C33 C34 C43 C42 178.6(2) . . . . ?
C33 C34 C43 C44 -4.5(3) . . . . ?
C34 C35 C36 C37 -173.4(2) . . . . ?
C34 C35 C36 C41 2.4(3) . . . . ?
C34 C43 C44 C45 177.8(2) . . . . ?
C34 C43 C44 C51 -5.3(4) . . . . ?
C35 C34 C43 C42 -1.9(3) . . . . ?
C35 C34 C43 C44 175.0(2) . . . . ?
C35 C36 C37 C38 -33.7(3) . . . . ?
C35 C36 C37 C39 -154.4(2) . . . . ?
C35 C36 C37 C40 87.0(3) . . . . ?
C35 C36 C41 C42 -2.4(3) . . . . ?
C36 C41 C42 C43 0.2(4) . . . . ?
C37 C36 C41 C42 173.5(2) . . . . ?
C41 C36 C37 C38 150.7(2) . . . . ?
C41 C36 C37 C39 30.0(3) . . . . ?
C41 C36 C37 C40 -88.6(3) . . . . ?
C41 C42 C43 C34 1.9(3) . . . . ?
C41 C42 C43 C44 -175.1(2) . . . . ?
C42 C43 C44 C45 -5.5(3) . . . . ?
C42 C43 C44 C51 171.4(2) . . . . ?
C43 C34 C35 C36 -0.3(3) . . . . ?
C43 C44 C45 C46 -68.8(3) . . . . ?
C43 C44 C45 C50 112.0(3) . . . . ?
C43 C44 C51 S2 5.8(3) . . . . ?
C43 C44 C51 C52 -178.3(2) . . . . ?
C44 C45 C46 C47 -177.5(2) . . . . ?
C44 C45 C50 C49 177.6(2) . . . . ?
C45 C44 C51 S2 -177.24(16) . . . . ?
C45 C44 C51 C52 -1.3(3) . . . . ?
C45 C46 C47 C48 -1.1(4) . . . . ?
C46 C45 C50 C49 -1.6(3) . . . . ?
C46 C47 C48 C49 0.5(4) . . . . ?
C47 C48 C49 C50 -0.4(4) . . . . ?
C48 C49 C50 C45 1.0(4) . . . . ?
C50 C45 C46 C47 1.6(3) . . . . ?
C51 S2 C33 N2 170.31(19) . . . . ?
C51 S2 C33 C34 -10.1(2) . . . . ?
C51 C44 C45 C46 114.1(3) . . . . ?
C51 C44 C45 C50 -65.0(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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.790
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and n-hexane'
