# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_exp_1419
_database_code_depnum_ccdc_archive 'CCDC 2053474'
loop_
_audit_author_name
_audit_author_address
'Bo Wen Pan'
;Guizhou University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2021-01-02 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_audit_creation_date             2020-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 O S'
_chemical_formula_sum            'C17 H14 O S'
_chemical_formula_weight         266.34
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.54810(10)
_cell_length_b                   11.5576(2)
_cell_length_c                   15.3921(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1342.77(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11352
_cell_measurement_temperature    99.9(9)
_cell_measurement_theta_max      74.7460
_cell_measurement_theta_min      4.7870
_shelx_estimated_absorpt_T_max   0.712
_shelx_estimated_absorpt_T_min   0.529
_exptl_absorpt_coefficient_mu    2.029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25631
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.785
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  -2.00   1.00    1.00    --    0.00 -38.00  30.00   86
  2  ω    -30.00  -3.00   1.00    1.00    --    0.00 -77.00 150.00   27
  3  ω    -17.00  13.00   1.00    1.00    --    0.00  38.00  30.00   30
  4  ω    -66.00 -36.00   1.00    1.00    --    0.00 -38.00-150.00   30
  5  ω    -80.00 -37.00   1.00    1.00    --    0.00 -77.00 150.00   43
  6  ω    -69.00  23.00   1.00    1.00    --    0.00 -57.00 150.00   92
  7  ω    -31.00  18.00   1.00    1.00    --    0.00 -38.00-150.00   49
  8  ω    -82.00  22.00   1.00    1.00    --    0.00 -57.00  90.00  104
  9  ω    -87.00  18.00   1.00    1.00    --    0.00 -19.00 -60.00  105
 10  ω    112.00 185.00   1.00    1.00    --   97.10  74.00  49.40   73
 11  ω     75.00 102.00   1.00    1.00    --   97.10  52.00 146.14   27
 12  ω     67.00  95.00   1.00    1.00    --   97.10  76.00  18.90   28
 13  ω    138.00 165.00   1.00    1.00    --   97.10  52.00 146.14   27
 14  ω     71.00  98.00   1.00    1.00    --   97.10  66.00  94.90   27
 15  ω     68.00 104.00   1.00    1.00    --   97.10  74.00  49.40   36
 16  ω     75.00 142.00   1.00    1.00    --   97.10  53.00 -16.43   67
 17  ω    122.00 164.00   1.00    1.00    --   97.10  72.00  -4.04   42
 18  ω     25.00  78.00   1.00    1.00    --   97.10 -82.00-150.00   53
 19  ω     67.00  94.00   1.00    1.00    --   97.10  82.00 120.00   27
 20  ω     70.00 118.00   1.00    1.00    --   97.10  72.00  -4.04   48
 21  ω     95.00 120.00   1.00    1.00    --   97.10 -82.00-150.00   25
 22  ω     68.00  93.00   1.00    1.00    --   97.10  77.00-180.00   25
 23  ω     67.00  94.00   1.00    1.00    --   97.10  77.00  30.00   27
 24  ω     66.00  91.00   1.00    1.00    --   97.10  82.00 -60.00   25
 25  ω     76.00 103.00   1.00    1.00    --   97.10  61.00-150.00   27
 26  ω     73.00  99.00   1.00    1.00    --   97.10  61.00 120.00   26
 27  ω     73.00  99.00   1.00    1.00    --   97.10  61.00-120.00   26
 28  ω    104.00 185.00   1.00    1.00    --   97.10  61.00-120.00   81
 29  ω     66.00  96.00   1.00    1.00    --   97.10  82.00  60.00   30
 30  ω    161.00 186.00   1.00    1.00    --   97.10  82.00  60.00   25
 31  ω     73.00 100.00   1.00    1.00    --   97.10  59.00 -16.30   27
 32  ω     85.00 128.00   1.00    1.00    --   97.10 -82.00  60.00   43
 33  ω     67.00 150.00   1.00    1.00    --   97.10  77.00 -60.00   83
 34  ω     68.00  95.00   1.00    1.00    --   97.10  77.00 -90.00   27
 35  ω      9.00  71.00   1.00    1.00    --   97.10 -82.00  60.00   62
 36  ω    148.00 175.00   1.00    1.00    --   97.10  58.00-128.30   27
 37  ω     19.00 130.00   1.00    1.00    --   97.10 -82.00 -30.00  111
 38  ω     66.00  93.00   1.00    1.00    --   97.10  82.00 -30.00   27
 39  ω     19.00 126.00   1.00    1.00    --   97.10 -82.00-180.00  107
 40  ω     67.00  94.00   1.00    1.00    --   97.10  77.00 150.00   27
 41  ω     69.00 163.00   1.00    1.00    --   97.10  77.00   0.00   94
 42  ω     76.00 107.00   1.00    1.00    --   97.10  56.00 -74.71   31
 43  ω     77.00 123.00   1.00    1.00    --   97.10  45.00-120.00   46
 44  ω     74.00  99.00   1.00    1.00    --   97.10  61.00-180.00   25
 45  ω     77.00 166.00   1.00    1.00    --   97.10  45.00-180.00   89
 46  ω     68.00  93.00   1.00    1.00    --   97.10  77.00  90.00   25
 47  ω     67.00  93.00   1.00    1.00    --   97.10  77.00 120.00   26
 48  ω    111.00 186.00   1.00    1.00    --   97.10  77.00  30.00   75
 49  ω     65.00  91.00   1.00    1.00    --   97.10  82.00-180.00   26
 50  ω    140.00 165.00   1.00    1.00    --   97.10  82.00-180.00   25
 51  ω     65.00  92.00   1.00    1.00    --   97.10  82.00   0.00   27
 52  ω     67.00  94.00   1.00    1.00    --   97.10  77.00 -30.00   27
 53  ω     78.00 119.00   1.00    1.00    --   97.10  45.00-150.00   41
 54  ω    130.00 155.00   1.00    1.00    --   97.10  45.00-150.00   25
 55  ω     77.00 115.00   1.00    1.00    --   97.10  45.00 150.00   38
 56  ω     75.00 101.00   1.00    1.00    --   97.10  61.00 -90.00   26
 57  ω     76.00 103.00   1.00    1.00    --   97.10  61.00 150.00   27
 58  ω    118.00 185.00   1.00    1.00    --   97.10  61.00 150.00   67
 59  ω    114.00 184.00   1.00    1.00    --   97.10  66.00  94.90   70
 60  ω     73.00  99.00   1.00    1.00    --   97.10  58.00-128.30   26
 61  ω     68.00  93.00   1.00    1.00    --   97.10  77.00-120.00   25
 62  ω     67.00  93.00   1.00    1.00    --   97.10  77.00  60.00   26
 63  ω     70.00 182.00   1.00    1.00    --   97.10  71.00 -69.21  112
 64  ω    161.00 186.00   1.00    1.00    --   97.10  77.00 120.00   25
 65  ω     77.00 104.00   1.00    1.00    --   97.10  45.00 -90.00   27
 66  ω    106.00 145.00   1.00    1.00    --   97.10  45.00 -90.00   39
 67  ω    154.00 181.00   1.00    1.00    --   97.10  45.00 -90.00   27
 68  ω     81.00 115.00   1.00    1.00    --   97.10  45.00  60.00   34
 69  ω    118.00 151.00   1.00    1.00    --   97.10  54.00 114.50   33
 70  ω     55.00 129.00   1.00    1.00    --   97.10 -82.00  30.00   74
 71  ω     75.00 106.00   1.00    1.00    --   97.10  54.00 114.50   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0682172000
_diffrn_orient_matrix_UB_12      -0.1239064000
_diffrn_orient_matrix_UB_13      -0.0151797000
_diffrn_orient_matrix_UB_21      -0.0117970000
_diffrn_orient_matrix_UB_22      -0.0187319000
_diffrn_orient_matrix_UB_23      0.0989595000
_diffrn_orient_matrix_UB_31      -0.1920841000
_diffrn_orient_matrix_UB_32      0.0451500000
_diffrn_orient_matrix_UB_33      -0.0006368000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2301
_reflns_number_total             2375
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.038
_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)+(0.0326P)²+0.2719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0613
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C4(H4), C11(H11), C5(H5), C13(H13), C2(H2), C1(H1), C3(H3)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 -0.01323(7) 0.51201(4) 0.29046(3) 0.02599(14) Uani 1 1 d . . . . .
O1 O 0.0310(2) 0.66928(13) 0.16669(9) 0.0310(4) Uani 1 1 d . . . . .
C10 C 0.3302(3) 0.53686(16) 0.32100(12) 0.0197(4) Uani 1 1 d . . . . .
C14 C 0.1913(3) 0.39458(17) 0.41470(13) 0.0240(4) Uani 1 1 d . . . . .
H14 H 0.091553 0.353369 0.432013 0.029 Uiso 1 1 calc R . . . .
C15 C 0.1810(3) 0.47625(17) 0.34853(12) 0.0221(4) Uani 1 1 d . . . . .
C12 C 0.5051(3) 0.43595(15) 0.42879(11) 0.0212(4) Uani 1 1 d . . . . .
C6 C 0.5019(3) 0.78147(15) 0.30887(12) 0.0226(4) Uani 1 1 d . . . . .
C9 C 0.2917(3) 0.61800(18) 0.24879(12) 0.0217(4) Uani 1 1 d . . . . .
C16 C 0.1032(3) 0.61320(18) 0.22325(13) 0.0248(5) Uani 1 1 d . . . . .
C4 C 0.7964(3) 0.81555(19) 0.36361(15) 0.0315(5) Uani 1 1 d . . . . .
H4 H 0.918430 0.813747 0.355359 0.038 Uiso 1 1 calc R . . . .
C11 C 0.4919(3) 0.51624(15) 0.36088(11) 0.0204(4) Uani 1 1 d . . . . .
H11 H 0.592197 0.555971 0.342437 0.025 Uiso 1 1 calc R . . . .
C7 C 0.3773(3) 0.74023(18) 0.24005(13) 0.0246(5) Uani 1 1 d . . . . .
H7 H 0.298499 0.799951 0.216639 0.030 Uiso 1 1 calc R . . . .
C5 C 0.6839(3) 0.77959(18) 0.29742(14) 0.0271(5) Uani 1 1 d . . . . .
H5 H 0.731151 0.754069 0.245019 0.033 Uiso 1 1 calc R . . . .
C13 C 0.3536(3) 0.37615(18) 0.45414(13) 0.0232(5) Uani 1 1 d . . . . .
H13 H 0.361712 0.322286 0.498851 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4252(3) 0.64742(19) 0.17756(13) 0.0257(5) Uani 1 1 d . . . . .
H8A H 0.542720 0.614036 0.182175 0.031 Uiso 1 1 calc R . . . .
H8B H 0.380883 0.654330 0.118634 0.031 Uiso 1 1 calc R . . . .
C17 C 0.6791(3) 0.41573(19) 0.47292(14) 0.0269(5) Uani 1 1 d . . . . .
H17A H 0.750806 0.365586 0.437771 0.040 Uiso 1 1 calc GR . . . .
H17B H 0.659136 0.380335 0.528489 0.040 Uiso 1 1 calc GR . . . .
H17C H 0.738872 0.488281 0.480797 0.040 Uiso 1 1 calc GR . . . .
C2 C 0.5458(3) 0.85658(19) 0.45372(15) 0.0348(6) Uani 1 1 d . . . . .
H2 H 0.498884 0.882327 0.506143 0.042 Uiso 1 1 calc R . . . .
C1 C 0.4337(3) 0.82089(18) 0.38787(14) 0.0297(5) Uani 1 1 d . . . . .
H1 H 0.311734 0.823159 0.396278 0.036 Uiso 1 1 calc R . . . .
C3 C 0.7273(3) 0.85408(19) 0.44182(16) 0.0331(5) Uani 1 1 d . . . . .
H3 H 0.802687 0.878128 0.486084 0.040 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C15 1.766(2) . ?
S1 C16 1.792(2) . ?
O1 C16 1.215(3) . ?
C10 C15 1.392(3) . ?
C10 C9 1.483(3) . ?
C10 C11 1.386(3) . ?
C14 C15 1.391(3) . ?
C14 C13 1.384(3) . ?
C12 C11 1.401(3) . ?
C12 C13 1.392(3) . ?
C12 C17 1.497(3) . ?
C6 C7 1.494(3) . ?
C6 C5 1.385(3) . ?
C6 C1 1.397(3) . ?
C9 C16 1.477(3) . ?
C9 C7 1.559(3) . ?
C9 C8 1.527(3) . ?
C4 C5 1.390(3) . ?
C4 C3 1.385(3) . ?
C7 C8 1.485(3) . ?
C2 C1 1.383(3) . ?
C2 C3 1.383(4) . ?

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
C15 S1 C16 92.16(10) . . ?
C15 C10 C9 112.80(18) . . ?
C11 C10 C15 119.39(18) . . ?
C11 C10 C9 127.81(19) . . ?
C13 C14 C15 118.38(19) . . ?
C10 C15 S1 113.57(15) . . ?
C14 C15 S1 125.16(16) . . ?
C14 C15 C10 121.27(19) . . ?
C11 C12 C17 120.30(19) . . ?
C13 C12 C11 118.6(2) . . ?
C13 C12 C17 121.06(17) . . ?
C5 C6 C7 121.92(19) . . ?
C5 C6 C1 118.8(2) . . ?
C1 C6 C7 119.3(2) . . ?
C10 C9 C7 123.80(18) . . ?
C10 C9 C8 123.33(19) . . ?
C16 C9 C10 111.37(18) . . ?
C16 C9 C7 114.22(18) . . ?
C16 C9 C8 116.92(17) . . ?
C8 C9 C7 57.52(14) . . ?
O1 C16 S1 122.83(17) . . ?
O1 C16 C9 127.1(2) . . ?
C9 C16 S1 110.09(15) . . ?
C3 C4 C5 120.2(2) . . ?
C10 C11 C12 120.46(19) . . ?
C6 C7 C9 119.24(17) . . ?
C8 C7 C6 122.4(2) . . ?
C8 C7 C9 60.15(13) . . ?
C6 C5 C4 120.5(2) . . ?
C14 C13 C12 121.86(19) . . ?
C7 C8 C9 62.32(14) . . ?
C1 C2 C3 120.2(2) . . ?
C2 C1 C6 120.7(2) . . ?
C2 C3 C4 119.6(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.938
_oxdiff_exptl_absorpt_empirical_full_min 0.622
####################################################################### 
# 
# 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_exp_1477
_database_code_depnum_ccdc_archive 'CCDC 2053475'
loop_
_audit_author_name
_audit_author_address
'Bo Wen Pan'
;Guizhou University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2021-01-02 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_audit_creation_date             2020-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 F O S'
_chemical_formula_sum            'C22 H17 F O S'
_chemical_formula_weight         348.41
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.6246(2)
_cell_length_b                   12.6387(3)
_cell_length_c                   10.4032(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.958(2)
_cell_angle_gamma                90
_cell_volume                     870.90(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6978
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.1480
_cell_measurement_theta_min      4.2300
_shelx_estimated_absorpt_T_max   0.815
_shelx_estimated_absorpt_T_min   0.566
_exptl_absorpt_coefficient_mu    1.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16182
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.015
_diffrn_reflns_theta_max         67.015
_diffrn_reflns_theta_min         4.250
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  14.00   1.00    1.00    --    0.00  57.00   0.00   30
  2  ω     38.00  89.00   1.00    1.00    --    0.00  57.00 150.00   51
  3  ω     35.00  89.00   1.00    1.00    --    0.00  57.00   0.00   54
  4  ω    -17.00  19.00   1.00    1.00    --    0.00  38.00  60.00   36
  5  ω    -17.00  38.00   1.00    1.00    --    0.00  38.00 -90.00   55
  6  ω     41.00  89.00   1.00    1.00    --    0.00  38.00  60.00   48
  7  ω    -22.00  10.00   1.00    1.00    --    0.00 -82.00 150.00   32
  8  ω    -87.00 -29.00   1.00    1.00    --    0.00 -82.00 150.00   58
  9  ω    -22.00  37.00   1.00    1.00    --    0.00  19.00   0.00   59
 10  ω    -30.00   3.00   1.00    1.00    --    0.00  77.00 120.00   33
 11  ω    -21.00  36.00   1.00    1.00    --    0.00  57.00 150.00   57
 12  ω    155.00 184.00   1.00    1.00    --   97.10  77.00 -60.00   29
 13  ω    149.00 176.00   1.00    1.00    --   97.10  57.00  45.94   27
 14  ω     67.00  93.00   1.00    1.00    --   97.10  77.00 120.00   26
 15  ω     80.00 129.00   1.00    1.00    --   97.10 -82.00 -60.00   49
 16  ω     24.00  72.00   1.00    1.00    --   97.10 -82.00 -60.00   48
 17  ω     74.00 127.00   1.00    1.00    --   97.10  57.00  45.94   53
 18  ω     70.00 118.00   1.00    1.00    --   97.10  69.00   1.36   48
 19  ω     85.00 110.00   1.00    1.00    --   97.10 -82.00  90.00   25
 20  ω    136.00 184.00   1.00    1.00    --   97.10  80.00-154.81   48
 21  ω     66.00  91.00   1.00    1.00    --   97.10  82.00  30.00   25
 22  ω      8.00 121.00   1.00    1.00    --   97.10 -61.00-120.00  113
 23  ω      9.00 128.00   1.00    1.00    --   97.10 -77.00   0.00  119
 24  ω     66.00  97.00   1.00    1.00    --   97.10  82.00 150.00   31
 25  ω     73.00 131.00   1.00    1.00    --   97.10  61.00  30.00   58
 26  ω     68.00 133.00   1.00    1.00    --   97.10  77.00 -60.00   65
 27  ω     77.00 185.00   1.00    1.00    --   97.10  45.00  90.00  108
 28  ω     67.00  93.00   1.00    1.00    --   97.10  77.00  60.00   26
 29  ω     73.00 184.00   1.00    1.00    --   97.10  61.00-150.00  111
 30  ω     76.00 110.00   1.00    1.00    --   97.10  61.00-120.00   34
 31  ω    114.00 161.00   1.00    1.00    --   97.10  77.00-120.00   47
 32  ω     66.00  92.00   1.00    1.00    --   97.10  80.00-154.81   26
 33  ω    129.00 165.00   1.00    1.00    --   97.10  74.00 -32.67   36
 34  ω     65.00  92.00   1.00    1.00    --   97.10  82.00 -90.00   27
 35  ω     68.00  95.00   1.00    1.00    --   97.10  77.00-120.00   27
 36  ω     73.00 125.00   1.00    1.00    --   97.10  61.00  90.00   52
 37  ω     67.00  93.00   1.00    1.00    --   97.10  77.00  90.00   26
 38  ω    150.00 175.00   1.00    1.00    --   97.10  77.00 -98.43   25
 39  ω     65.00  92.00   1.00    1.00    --   97.10  82.00  90.00   27
 40  ω     76.00 178.00   1.00    1.00    --   97.10  61.00 -90.00  102
 41  ω     67.00  93.00   1.00    1.00    --   97.10  77.00   0.00   26
 42  ω    120.00 186.00   1.00    1.00    --   97.10  77.00   0.00   66
 43  ω     67.00 112.00   1.00    1.00    --   97.10  77.00-180.00   45
 44  ω     73.00 100.00   1.00    1.00    --   97.10  61.00  60.00   27
 45  ω     65.00 132.00   1.00    1.00    --   97.10  82.00 -30.00   67
 46  ω     73.00 150.00   1.00    1.00    --   97.10  61.00 120.00   77
 47  ω     67.00  94.00   1.00    1.00    --   97.10  77.00  30.00   27
 48  ω     67.00  93.00   1.00    1.00    --   97.10  77.00 150.00   26
 49  ω     66.00  91.00   1.00    1.00    --   97.10  82.00-150.00   25
 50  ω     66.00  93.00   1.00    1.00    --   97.10  82.00 -60.00   27
 51  ω     74.00 118.00   1.00    1.00    --   97.10  61.00 150.00   44
 52  ω     74.00 179.00   1.00    1.00    --   97.10  61.00 -60.00  105
 53  ω     68.00  93.00   1.00    1.00    --   97.10  77.00 -98.43   25
 54  ω     79.00 142.00   1.00    1.00    --   97.10  30.00-150.00   63
 55  ω     68.00  94.00   1.00    1.00    --   97.10  74.00 -32.67   26
 56  ω     10.00  51.00   1.00    1.00    --   97.10 -82.00  60.00   41
 57  ω     73.00 128.00   1.00    1.00    --   97.10 -82.00  60.00   55
 58  ω    134.00 167.00   1.00    1.00    --   97.10  67.00 152.72   33
 59  ω     31.00 108.00   1.00    1.00    --   97.10 -82.00-150.00   77
 60  ω     73.00 133.00   1.00    1.00    --   97.10  67.00 152.72   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0411547000
_diffrn_orient_matrix_UB_12      -0.1059168000
_diffrn_orient_matrix_UB_13      0.0689605000
_diffrn_orient_matrix_UB_21      -0.0082071000
_diffrn_orient_matrix_UB_22      0.0564666000
_diffrn_orient_matrix_UB_23      0.1310618000
_diffrn_orient_matrix_UB_31      -0.2286758000
_diffrn_orient_matrix_UB_32      -0.0211207000
_diffrn_orient_matrix_UB_33      0.0051909000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2830
_reflns_number_total             3057
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 1149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.037
_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)+(0.1217P)²+0.8486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1874
_refine_ls_wR_factor_ref         0.1912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C17(H17), C2(H2), C15(H15), C16(H16), C18(H18), C13(H13),
 C21(H21), C20(H20)
2.c 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
S1 S 0.0721(2) 0.54265(15) 0.97190(15) 0.0470(5) Uani 1 1 d . . . . .
F1 F -0.0511(7) 0.3154(4) 0.6863(6) 0.0690(15) Uani 1 1 d . . . . .
O1 O 0.0775(8) 0.3333(5) 0.9860(5) 0.0571(15) Uani 1 1 d . . . . .
C6 C 0.4019(9) 0.5230(5) 0.8350(5) 0.0349(14) Uani 1 1 d . . . . .
C5 C 0.5781(8) 0.5554(5) 0.7752(5) 0.0333(13) Uani 1 1 d . . . . .
H5 H 0.661246 0.506000 0.736247 0.040 Uiso 1 1 calc R . . . .
C4 C 0.6291(10) 0.6629(5) 0.7741(6) 0.0344(14) Uani 1 1 d . . . . .
C7 C 0.3268(9) 0.4130(5) 0.8471(6) 0.0356(14) Uani 1 1 d . . . . .
C10 C 0.3018(9) 0.3410(5) 0.7270(6) 0.0361(14) Uani 1 1 d . . . . .
C19 C 0.4278(11) 0.4917(5) 0.3692(7) 0.0426(16) Uani 1 1 d . . . . .
C1 C 0.2802(10) 0.5975(6) 0.8942(6) 0.0396(15) Uani 1 1 d . . . . .
C3 C 0.5054(11) 0.7360(6) 0.8333(7) 0.0418(16) Uani 1 1 d . . . . .
H3 H 0.540878 0.807219 0.832820 0.050 Uiso 1 1 calc R . . . .
C9 C 0.4584(10) 0.3169(6) 0.8292(6) 0.0384(14) Uani 1 1 d . . . . .
H9A H 0.598770 0.328636 0.808276 0.046 Uiso 1 1 calc R . . . .
H9B H 0.434951 0.256459 0.884457 0.046 Uiso 1 1 calc R . . . .
C14 C 0.5703(10) 0.4247(5) 0.4176(7) 0.0435(16) Uani 1 1 d . . . . .
C12 C 0.3536(10) 0.3901(6) 0.6008(6) 0.0408(15) Uani 1 1 d . . . . .
C17 C 0.6456(14) 0.5192(6) 0.1849(7) 0.055(2) Uani 1 1 d . . . . .
H17 H 0.668566 0.548342 0.104372 0.067 Uiso 1 1 calc R . . . .
C22 C 0.8195(10) 0.6987(6) 0.7069(7) 0.0418(16) Uani 1 1 d . . . . .
H22A H 0.918566 0.720349 0.769986 0.063 Uiso 1 1 calc GR . . . .
H22B H 0.788106 0.757065 0.651043 0.063 Uiso 1 1 calc GR . . . .
H22C H 0.872092 0.641184 0.657320 0.063 Uiso 1 1 calc GR . . . .
C2 C 0.3311(12) 0.7051(6) 0.8929(6) 0.0422(16) Uani 1 1 d . . . . .
H2 H 0.248469 0.754807 0.931714 0.051 Uiso 1 1 calc R . . . .
C15 C 0.7555(11) 0.4046(6) 0.3583(7) 0.0462(16) Uani 1 1 d . . . . .
H15 H 0.850224 0.359801 0.396586 0.055 Uiso 1 1 calc R . . . .
C16 C 0.7940(13) 0.4521(6) 0.2432(7) 0.0510(17) Uani 1 1 d . . . . .
H16 H 0.916498 0.440768 0.203103 0.061 Uiso 1 1 calc R . . . .
C8 C 0.1551(9) 0.4105(6) 0.9395(6) 0.0447(18) Uani 1 1 d . . . . .
C18 C 0.4724(11) 0.5406(6) 0.2458(6) 0.0471(15) Uani 1 1 d . . . . .
H18 H 0.379868 0.587268 0.208581 0.057 Uiso 1 1 calc R . . . .
C11 C 0.1283(10) 0.2632(6) 0.7185(8) 0.0470(17) Uani 1 1 d . . . . .
H11A H 0.156523 0.210109 0.653872 0.056 Uiso 1 1 calc R . . . .
H11B H 0.113968 0.227596 0.800406 0.056 Uiso 1 1 calc R . . . .
C13 C 0.5269(11) 0.3722(6) 0.5400(6) 0.0442(16) Uani 1 1 d . . . . .
H13 H 0.621199 0.325835 0.575911 0.053 Uiso 1 1 calc R . . . .
C21 C 0.2147(13) 0.4658(6) 0.5458(7) 0.0493(18) Uani 1 1 d . . . . .
H21 H 0.098892 0.482655 0.590753 0.059 Uiso 1 1 calc R . . . .
C20 C 0.2459(11) 0.5133(6) 0.4314(7) 0.0481(17) Uani 1 1 d . . . . .
H20 H 0.150196 0.558731 0.395244 0.058 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.752(7) . ?
S1 C8 1.792(8) . ?
F1 C11 1.395(8) . ?
O1 C8 1.208(9) . ?
C6 C5 1.394(8) . ?
C6 C7 1.483(9) . ?
C6 C1 1.389(9) . ?
C5 H5 0.9300 . ?
C5 C4 1.400(10) . ?
C4 C3 1.386(10) . ?
C4 C22 1.521(10) . ?
C7 C10 1.552(9) . ?
C7 C9 1.509(10) . ?
C7 C8 1.502(8) . ?
C10 C9 1.504(9) . ?
C10 C12 1.498(8) . ?
C10 C11 1.514(9) . ?
C19 C14 1.359(10) . ?
C19 C18 1.460(11) . ?
C19 C20 1.404(11) . ?
C1 C2 1.402(11) . ?
C3 H3 0.9300 . ?
C3 C2 1.376(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 C15 1.406(10) . ?
C14 C13 1.469(10) . ?
C12 C13 1.339(10) . ?
C12 C21 1.439(10) . ?
C17 H17 0.9300 . ?
C17 C16 1.425(12) . ?
C17 C18 1.347(11) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.367(11) . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.352(10) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C8 92.0(3) . . ?
C5 C6 C7 126.7(6) . . ?
C1 C6 C5 119.7(6) . . ?
C1 C6 C7 113.5(6) . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.5(6) . . ?
C4 C5 H5 120.3 . . ?
C5 C4 C22 119.6(6) . . ?
C3 C4 C5 119.9(6) . . ?
C3 C4 C22 120.5(6) . . ?
C6 C7 C10 120.9(5) . . ?
C6 C7 C9 123.3(5) . . ?
C6 C7 C8 109.4(6) . . ?
C9 C7 C10 58.8(4) . . ?
C8 C7 C10 115.5(6) . . ?
C8 C7 C9 120.5(6) . . ?
C9 C10 C7 59.1(4) . . ?
C9 C10 C11 115.1(5) . . ?
C12 C10 C7 116.1(5) . . ?
C12 C10 C9 122.6(6) . . ?
C12 C10 C11 113.7(5) . . ?
C11 C10 C7 119.9(6) . . ?
C14 C19 C18 116.1(7) . . ?
C14 C19 C20 123.1(7) . . ?
C20 C19 C18 120.7(6) . . ?
C6 C1 S1 113.8(6) . . ?
C6 C1 C2 120.7(6) . . ?
C2 C1 S1 125.4(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.2(7) . . ?
C2 C3 H3 119.4 . . ?
C7 C9 H9A 117.6 . . ?
C7 C9 H9B 117.6 . . ?
C10 C9 C7 62.0(4) . . ?
C10 C9 H9A 117.6 . . ?
C10 C9 H9B 117.6 . . ?
H9A C9 H9B 114.7 . . ?
C19 C14 C15 123.8(7) . . ?
C19 C14 C13 117.3(7) . . ?
C15 C14 C13 119.0(6) . . ?
C13 C12 C10 123.7(6) . . ?
C13 C12 C21 118.2(6) . . ?
C21 C12 C10 118.0(6) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.4(7) . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(6) . . ?
C3 C2 H2 120.5 . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.8(7) . . ?
C16 C15 H15 120.6 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.8(7) . . ?
C15 C16 H16 120.1 . . ?
O1 C8 S1 123.0(5) . . ?
O1 C8 C7 127.2(7) . . ?
C7 C8 S1 109.8(5) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 C19 121.0(7) . . ?
C17 C18 H18 119.5 . . ?
F1 C11 C10 110.5(6) . . ?
F1 C11 H11A 109.6 . . ?
F1 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 121.0(7) . . ?
C12 C13 H13 119.5 . . ?
C12 C21 H21 118.7 . . ?
C20 C21 C12 122.6(7) . . ?
C20 C21 H21 118.7 . . ?
C19 C20 H20 121.2 . . ?
C21 C20 C19 117.7(7) . . ?
C21 C20 H20 121.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 16.968
_oxdiff_exptl_absorpt_empirical_full_min 0.380
####################################################################### 
# 
# 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_exp_1543
_database_code_depnum_ccdc_archive 'CCDC 2053476'
loop_
_audit_author_name
_audit_author_address
'Bo Wen Pan'
;Guizhou University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2021-01-02 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_audit_creation_date             2020-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N O2 S'
_chemical_formula_sum            'C25 H23 N O2 S'
_chemical_formula_weight         401.50
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.40850(10)
_cell_length_b                   9.74720(10)
_cell_length_c                   25.2684(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2070.98(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23397
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1820
_cell_measurement_theta_min      3.5180
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.591
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            48728
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.703
_diffrn_reflns_theta_min         3.498
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  77.00   1.00    1.00    --    0.00  77.00   0.00   34
  2  ω    -76.00 -20.00   1.00    1.00    --    0.00 -82.00   0.00   56
  3  ω    -18.00  28.00   1.00    1.00    --    0.00  38.00 -30.00   46
  4  ω    -19.00   7.00   1.00    1.00    --    0.00  57.00   0.00   26
  5  ω    -18.00  89.00   1.00    1.00    --    0.00  38.00-150.00  107
  6  ω    -28.00  37.00   1.00    1.00    --    0.00  77.00   0.00   65
  7  ω     56.00  83.00   1.00    1.00    --    0.00  19.00  30.00   27
  8  ω    -23.00  85.00   1.00    1.00    --    0.00  57.00 120.00  108
  9  ω     -9.00  32.00   1.00    1.00    --    0.00 -82.00   0.00   41
 10  ω     42.00  67.00   1.00    1.00    --    0.00  57.00   0.00   25
 11  ω    -24.00  25.00   1.00    1.00    --    0.00  19.00  30.00   49
 12  ω    -20.00  28.00   1.00    1.00    --    0.00  82.00 -60.00   48
 13  ω    145.00 171.00   1.00    1.00    --   95.80  76.00-123.80   26
 14  ω     65.00 122.00   1.00    1.00    --   95.80  76.00-123.80   57
 15  ω    130.00 156.00   1.00    1.00    --   95.80  74.00 -67.43   26
 16  ω    146.00 181.00   1.00    1.00    --   95.80  77.00  41.95   35
 17  ω     65.00  93.00   1.00    1.00    --   95.80  77.00  41.95   28
 18  ω     66.00  92.00   1.00    1.00    --   95.80  74.00 -67.43   26
 19  ω     70.00 185.00   1.00    1.00    --   95.80  64.00 -63.16  115
 20  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 21  ω    123.00 185.00   1.00    1.00    --   95.80  82.00 150.00   62
 22  ω     94.00 184.00   1.00    1.00    --   95.80  82.00-163.36   90
 23  ω     72.00  97.00   1.00    1.00    --   95.80  61.00  90.00   25
 24  ω    119.00 144.00   1.00    1.00    --   95.80  82.00-120.00   25
 25  ω      6.00 127.00   1.00    1.00    --   95.80 -82.00 150.00  121
 26  ω     72.00 179.00   1.00    1.00    --   95.80  61.00 -90.00  107
 27  ω     55.00 112.00   1.00    1.00    --   95.80 -82.00 -60.00   57
 28  ω     63.00  90.00   1.00    1.00    --   95.80  82.00   0.00   27
 29  ω     63.00  90.00   1.00    1.00    --   95.80  82.00 120.00   27
 30  ω     65.00  92.00   1.00    1.00    --   95.80  77.00  60.00   27
 31  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 32  ω     80.00 128.00   1.00    1.00    --   95.80 -82.00-180.00   48
 33  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-163.36   26
 34  ω    124.00 151.00   1.00    1.00    --   95.80  57.00-160.02   27
 35  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 36  ω      8.00 127.00   1.00    1.00    --   95.80 -82.00  90.00  119
 37  ω     46.00  75.00   1.00    1.00    --   95.80 -82.00-180.00   29
 38  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 39  ω    112.00 182.00   1.00    1.00    --   95.80  77.00  90.00   70
 40  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 41  ω     63.00 127.00   1.00    1.00    --   95.80  82.00-150.00   64
 42  ω     76.00 185.00   1.00    1.00    --   95.80  45.00 150.00  109
 43  ω     45.00 123.00   1.00    1.00    --   95.80 -82.00   0.00   78
 44  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 45  ω     65.00  91.00   1.00    1.00    --   95.80  78.00 -19.90   26
 46  ω    140.00 167.00   1.00    1.00    --   95.80  77.00 -30.00   27
 47  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 48  ω     64.00  89.00   1.00    1.00    --   95.80  82.00-120.00   25
 49  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 50  ω    160.00 185.00   1.00    1.00    --   95.80  82.00-120.00   25
 51  ω     71.00  97.00   1.00    1.00    --   95.80  61.00   0.00   26
 52  ω     50.00  88.00   1.00    1.00    --   95.80 -82.00-150.00   38
 53  ω     94.00 128.00   1.00    1.00    --   95.80 -82.00-150.00   34
 54  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 55  ω     63.00  90.00   1.00    1.00    --   95.80  82.00  60.00   27
 56  ω     76.00 102.00   1.00    1.00    --   95.80  45.00 120.00   26
 57  ω    143.00 170.00   1.00    1.00    --   95.80  45.00 120.00   27
 58  ω     71.00  99.00   1.00    1.00    --   95.80  61.00-150.00   28
 59  ω     75.00 183.00   1.00    1.00    --   95.80  45.00  60.00  108
 60  ω    116.00 183.00   1.00    1.00    --   95.80  61.00 120.00   67
 61  ω     71.00  97.00   1.00    1.00    --   95.80  61.00 150.00   26
 62  ω     66.00 108.00   1.00    1.00    --   95.80  74.00 -46.60   42
 63  ω     75.00 184.00   1.00    1.00    --   95.80  45.00  30.00  109
 64  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 65  ω     72.00  97.00   1.00    1.00    --   95.80  61.00 120.00   25
 66  ω     64.00  90.00   1.00    1.00    --   95.80  79.00  21.27   26
 67  ω     72.00 105.00   1.00    1.00    --   95.80  57.00-160.02   33
 68  ω    110.00 178.00   1.00    1.00    --   95.80  55.00  -8.68   68
 69  ω     72.00  99.00   1.00    1.00    --   95.80  55.00  -8.68   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0405018000
_diffrn_orient_matrix_UB_12      -0.0767002000
_diffrn_orient_matrix_UB_13      -0.0515849000
_diffrn_orient_matrix_UB_21      -0.0612016000
_diffrn_orient_matrix_UB_22      -0.1227929000
_diffrn_orient_matrix_UB_23      0.0324983000
_diffrn_orient_matrix_UB_31      -0.1679386000
_diffrn_orient_matrix_UB_32      0.0632434000
_diffrn_orient_matrix_UB_33      0.0006138000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4043
_reflns_number_total             4211
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.107
_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)+(0.0383P)²+0.8147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_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
C1 C 0.7691(3) 0.1430(3) 0.35476(11) 0.0248(5) Uani 1 1 d . . . . .
C2 C 0.7482(4) 0.0222(3) 0.38277(12) 0.0309(7) Uani 1 1 d . . . . .
H2 H 0.757032 -0.062195 0.365887 0.037 Uiso 1 1 calc R . . . .
C3 C 0.7140(4) 0.0292(3) 0.43627(12) 0.0325(7) Uani 1 1 d . . . . .
H3 H 0.700424 -0.051678 0.455292 0.039 Uiso 1 1 calc R . . . .
C4 C 0.6996(3) 0.1546(3) 0.46227(10) 0.0277(6) Uani 1 1 d . . . . .
C5 C 0.7225(3) 0.2751(3) 0.43302(10) 0.0227(6) Uani 1 1 d . . . . .
H5 H 0.713597 0.359459 0.449961 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7581(3) 0.2717(2) 0.37934(10) 0.0204(5) Uani 1 1 d . . . . .
C7 C 0.7830(3) 0.3923(2) 0.34246(9) 0.0191(5) Uani 1 1 d . . . . .
C8 C 0.8240(3) 0.3313(3) 0.28763(10) 0.0229(5) Uani 1 1 d . . . . .
C9 C 0.6301(3) 0.4804(2) 0.33352(9) 0.0188(5) Uani 1 1 d . . . . .
H9 H 0.651524 0.545451 0.304828 0.023 Uiso 1 1 calc R . . . .
C10 C 0.4887(3) 0.3939(2) 0.31776(10) 0.0196(5) Uani 1 1 d . . . . .
C11 C 0.4471(4) 0.3864(3) 0.26422(10) 0.0242(6) Uani 1 1 d . . . . .
H11 H 0.503409 0.437556 0.239438 0.029 Uiso 1 1 calc R . . . .
C12 C 0.3224(4) 0.3033(3) 0.24778(11) 0.0278(6) Uani 1 1 d . . . . .
H12 H 0.296104 0.298378 0.212088 0.033 Uiso 1 1 calc R . . . .
C13 C 0.2372(4) 0.2275(3) 0.28457(12) 0.0295(6) Uani 1 1 d . . . . .
H13 H 0.155184 0.170272 0.273507 0.035 Uiso 1 1 calc R . . . .
C14 C 0.2744(3) 0.2371(3) 0.33769(11) 0.0277(6) Uani 1 1 d . . . . .
H14 H 0.215045 0.188635 0.362461 0.033 Uiso 1 1 calc R . . . .
C15 C 0.4002(3) 0.3190(3) 0.35428(11) 0.0245(6) Uani 1 1 d . . . . .
H15 H 0.425529 0.323784 0.390066 0.029 Uiso 1 1 calc R . . . .
C16 C 0.9213(3) 0.4892(2) 0.35810(10) 0.0198(5) Uani 1 1 d . . . . .
H16A H 1.010068 0.434693 0.370681 0.024 Uiso 1 1 calc R . . . .
H16B H 0.956290 0.539213 0.327030 0.024 Uiso 1 1 calc R . . . .
C17 C 0.8734(3) 0.5909(2) 0.40087(9) 0.0188(5) Uani 1 1 d . . . . .
H17 H 0.853584 0.541034 0.433898 0.023 Uiso 1 1 calc R . . . .
C18 C 0.4591(3) 0.6478(3) 0.37741(11) 0.0260(6) Uani 1 1 d . . . . .
H18A H 0.464825 0.698505 0.344894 0.039 Uiso 1 1 calc GR . . . .
H18B H 0.455364 0.710484 0.406682 0.039 Uiso 1 1 calc GR . . . .
H18C H 0.364953 0.592039 0.377419 0.039 Uiso 1 1 calc GR . . . .
C19 C 0.9911(3) 0.7044(2) 0.41132(10) 0.0186(5) Uani 1 1 d . . . . .
C20 C 1.0206(3) 0.7446(3) 0.46322(10) 0.0243(5) Uani 1 1 d . . . . .
H20 H 0.972247 0.697532 0.490889 0.029 Uiso 1 1 calc R . . . .
C21 C 1.1212(4) 0.8538(3) 0.47438(10) 0.0291(6) Uani 1 1 d . . . . .
H21 H 1.138973 0.879875 0.509280 0.035 Uiso 1 1 calc R . . . .
C22 C 1.1951(4) 0.9240(3) 0.43336(11) 0.0283(6) Uani 1 1 d . . . . .
H22 H 1.263526 0.996579 0.440653 0.034 Uiso 1 1 calc R . . . .
C23 C 1.1661(3) 0.8850(2) 0.38132(10) 0.0248(6) Uani 1 1 d . . . . .
H23 H 1.215357 0.931733 0.353720 0.030 Uiso 1 1 calc R . . . .
C24 C 1.0642(3) 0.7768(2) 0.37033(10) 0.0216(5) Uani 1 1 d . . . . .
H24 H 1.044330 0.752347 0.335374 0.026 Uiso 1 1 calc R . . . .
C25 C 0.6591(5) 0.1613(3) 0.52019(11) 0.0413(8) Uani 1 1 d . . . . .
H25A H 0.549825 0.187811 0.524287 0.062 Uiso 1 1 calc GR . . . .
H25B H 0.726212 0.227628 0.537248 0.062 Uiso 1 1 calc GR . . . .
H25C H 0.675436 0.072908 0.536004 0.062 Uiso 1 1 calc GR . . . .
N1 N 0.5997(3) 0.5597(2) 0.38233(8) 0.0195(5) Uani 1 1 d . . . . .
O1 O 0.8597(2) 0.39862(19) 0.24948(7) 0.0277(4) Uani 1 1 d . . . . .
O2 O 0.7297(2) 0.66060(17) 0.38510(7) 0.0198(4) Uani 1 1 d . . . . .
S1 S 0.81013(9) 0.15043(7) 0.28646(3) 0.02808(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.385(4) . ?
C1 C6 1.403(3) . ?
C1 S1 1.761(3) . ?
C2 C3 1.384(4) . ?
C3 C4 1.393(4) . ?
C4 C5 1.401(3) . ?
C4 C25 1.504(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.515(3) . ?
C7 C8 1.547(3) . ?
C7 C9 1.562(4) . ?
C7 C16 1.549(4) . ?
C8 O1 1.204(3) . ?
C8 S1 1.767(3) . ?
C9 C10 1.510(4) . ?
C9 N1 1.478(3) . ?
C10 C11 1.399(4) . ?
C10 C15 1.392(4) . ?
C11 C12 1.389(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.381(4) . ?
C14 C15 1.390(4) . ?
C16 C17 1.521(3) . ?
C17 C19 1.508(4) . ?
C17 O2 1.442(3) . ?
C18 N1 1.467(3) . ?
C19 C20 1.391(4) . ?
C19 C24 1.396(4) . ?
C20 C21 1.388(4) . ?
C21 C22 1.389(4) . ?
C22 C23 1.390(4) . ?
C23 C24 1.387(4) . ?
N1 O2 1.472(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.7(2) . . ?
C2 C1 S1 124.1(2) . . ?
C6 C1 S1 114.2(2) . . ?
C3 C2 C1 119.0(3) . . ?
C2 C3 C4 121.4(3) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 C25 121.1(2) . . ?
C5 C4 C25 120.5(3) . . ?
C6 C5 C4 121.6(2) . . ?
C1 C6 C7 114.4(2) . . ?
C5 C6 C1 117.9(2) . . ?
C5 C6 C7 127.7(2) . . ?
C6 C7 C8 106.46(19) . . ?
C6 C7 C9 113.7(2) . . ?
C6 C7 C16 114.8(2) . . ?
C8 C7 C9 105.40(19) . . ?
C8 C7 C16 107.2(2) . . ?
C16 C7 C9 108.65(19) . . ?
C7 C8 S1 112.58(17) . . ?
O1 C8 C7 124.3(2) . . ?
O1 C8 S1 123.1(2) . . ?
C10 C9 C7 112.28(19) . . ?
N1 C9 C7 107.99(19) . . ?
N1 C9 C10 112.1(2) . . ?
C11 C10 C9 118.8(2) . . ?
C15 C10 C9 122.6(2) . . ?
C15 C10 C11 118.7(2) . . ?
C12 C11 C10 120.6(3) . . ?
C13 C12 C11 120.0(3) . . ?
C14 C13 C12 119.9(3) . . ?
C13 C14 C15 120.3(3) . . ?
C14 C15 C10 120.5(3) . . ?
C17 C16 C7 112.3(2) . . ?
C19 C17 C16 115.4(2) . . ?
O2 C17 C16 109.4(2) . . ?
O2 C17 C19 104.64(19) . . ?
C20 C19 C17 119.2(2) . . ?
C20 C19 C24 118.6(2) . . ?
C24 C19 C17 122.0(2) . . ?
C21 C20 C19 121.1(2) . . ?
C20 C21 C22 119.9(2) . . ?
C21 C22 C23 119.5(3) . . ?
C24 C23 C22 120.4(2) . . ?
C23 C24 C19 120.5(2) . . ?
C18 N1 C9 112.0(2) . . ?
C18 N1 O2 102.21(18) . . ?
O2 N1 C9 105.14(18) . . ?
C17 O2 N1 108.69(16) . . ?
C1 S1 C8 92.14(12) . . ?

_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 3.638
_oxdiff_exptl_absorpt_empirical_full_min 0.510
