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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_wht-20240119_auto
_database_code_depnum_ccdc_archive 'CCDC 2345330'
_audit_update_record             
;
2024-04-02 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2024-01-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O S'
_chemical_formula_sum            'C16 H19 N O S'
_chemical_formula_weight         273.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   24.0035(14)
_cell_length_b                   7.3302(6)
_cell_length_c                   17.4293(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.762(5)
_cell_angle_gamma                90
_cell_volume                     3063.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.4730
_cell_measurement_theta_min      5.0770
_shelx_estimated_absorpt_T_max   0.614
_shelx_estimated_absorpt_T_min   0.614
_exptl_absorpt_coefficient_mu    1.802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6228
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.085
_diffrn_reflns_theta_min         3.687
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_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    -52.00  16.00   1.00    1.00    --  -35.62  45.00-173.00   68
  2  ω   -104.00 -48.00   1.00    1.00    --  -35.62 -45.00  36.00   56
  3  ω      3.00  49.00   1.00    1.00    --   35.62 -45.00  36.00   46
  4  ω     59.00 103.00   1.00    1.00    --   35.62  45.00-173.00   44
  5  ω     91.00 172.00   1.00    3.61    --  106.81  45.00-173.00   81
  6  ω     41.00 123.00   1.00    3.61    --  106.81 -45.00  36.00   82
  7  ω   -108.00 -37.00   1.00    1.00    --  -35.62 178.00 -90.00   71
  8  ω    -33.00  47.00   1.00    1.00    --   35.62 -38.00 -90.00   80
  9  ω     72.00  99.00   1.00    1.00    --   35.62 178.00   0.00   27
 10  ω     39.00 118.00   1.00    3.61    --  106.81 -45.00-120.00   79
 11  ω    112.00 172.00   1.00    3.61    --  106.81 111.00  30.00   60
 12  ω    112.00 173.00   1.00    3.61    --  106.81  77.00 150.00   61
 13  ω     51.00  78.00   1.00    3.61    --  106.81-111.00-150.00   27
 14  ω     74.00 178.00   1.00    3.61    --  106.81  15.00 120.00  104
 15  ω    121.00 147.00   1.00    3.61    --  106.81 111.00-150.00   26
 16  ω     82.00 108.00   1.00    3.61    --  106.81 -45.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0623011000
_diffrn_orient_matrix_UB_12      0.0452642000
_diffrn_orient_matrix_UB_13      -0.0058715000
_diffrn_orient_matrix_UB_21      0.0009667000
_diffrn_orient_matrix_UB_22      -0.1093435000
_diffrn_orient_matrix_UB_23      -0.0753785000
_diffrn_orient_matrix_UB_31      -0.0156274000
_diffrn_orient_matrix_UB_32      0.1738285000
_diffrn_orient_matrix_UB_33      -0.0459304000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2133
_reflns_number_total             2904
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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         0.223
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.039
_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     175
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0548
_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)+(0.0675P)²+1.0034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1630
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C16(H16), C6(H6), C4(H4), C5(H5)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C15(H15A,H15B,H15C)
;
_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
S12 S 0.27608(3) 0.61890(13) 0.66737(4) 0.0730(3) Uani 1 1 d . . . . .
O14 O 0.25519(10) 0.4956(4) 0.52824(13) 0.0928(8) Uani 1 1 d . . . . .
N8 N 0.50063(9) 0.7587(4) 0.50108(16) 0.0684(6) Uani 1 1 d . . . . .
C2 C 0.41295(10) 0.6733(4) 0.46795(15) 0.0559(6) Uani 1 1 d . . . . .
C1 C 0.42092(10) 0.6627(4) 0.54938(14) 0.0552(6) Uani 1 1 d . . . . .
C11 C 0.33063(11) 0.7301(4) 0.61431(14) 0.0569(6) Uani 1 1 d . . . . .
H11 H 0.314717 0.766114 0.563725 0.068 Uiso 1 1 calc R U . . .
C9 C 0.47461(11) 0.7148(4) 0.56753(17) 0.0635(7) Uani 1 1 d . . . . .
C3 C 0.36833(12) 0.6367(4) 0.41567(16) 0.0668(7) Uani 1 1 d . . . . .
H3 H 0.334336 0.597325 0.433063 0.080 Uiso 1 1 calc R U . . .
C10 C 0.37845(11) 0.5959(4) 0.60283(15) 0.0621(7) Uani 1 1 d . . . . .
H10A H 0.396944 0.570421 0.652375 0.075 Uiso 1 1 calc R U . . .
H10B H 0.362925 0.482190 0.583003 0.075 Uiso 1 1 calc R U . . .
C7 C 0.46394(11) 0.7330(4) 0.43940(17) 0.0625(7) Uani 1 1 d . . . . .
C16 C 0.34809(13) 0.8994(5) 0.65762(17) 0.0698(8) Uani 1 1 d . . . . .
H16 H 0.371999 0.885609 0.700824 0.084 Uiso 1 1 calc R U . . .
C13 C 0.24189(12) 0.4904(5) 0.59364(18) 0.0724(8) Uani 1 1 d . . . . .
C6 C 0.47052(15) 0.7582(5) 0.3614(2) 0.0839(10) Uani 1 1 d . . . . .
H6 H 0.504105 0.799171 0.343189 0.101 Uiso 1 1 calc R U . . .
C4 C 0.37506(15) 0.6594(6) 0.33859(17) 0.0845(10) Uani 1 1 d . . . . .
H4 H 0.345543 0.633855 0.303718 0.101 Uiso 1 1 calc R U . . .
C18 C 0.50496(15) 0.7266(6) 0.6444(2) 0.0912(11) Uani 1 1 d . . . . .
H18A H 0.537466 0.650271 0.644756 0.137 Uiso 1 1 calc R U . . .
H18B H 0.480887 0.686581 0.683421 0.137 Uiso 1 1 calc R U . . .
H18C H 0.516008 0.850633 0.654198 0.137 Uiso 1 1 calc R U . . .
C19 C 0.55889(12) 0.8153(5) 0.4966(3) 0.0908(11) Uani 1 1 d . . . . .
H19A H 0.565127 0.924765 0.526005 0.136 Uiso 1 1 calc R U . . .
H19B H 0.566811 0.837812 0.443975 0.136 Uiso 1 1 calc R U . . .
H19C H 0.582915 0.720427 0.516891 0.136 Uiso 1 1 calc R U . . .
C5 C 0.42560(17) 0.7203(6) 0.31186(19) 0.0937(12) Uani 1 1 d . . . . .
H5 H 0.429056 0.735647 0.259337 0.112 Uiso 1 1 calc R U . . .
C17 C 0.33237(17) 1.0624(5) 0.6393(2) 0.0959(11) Uani 1 1 d . . . . .
H17A H 0.308477 1.081463 0.596437 0.115 Uiso 1 1 calc R U . . .
H17B H 0.344927 1.161068 0.668901 0.115 Uiso 1 1 calc R U . . .
C15 C 0.19522(15) 0.3758(6) 0.6209(3) 0.1034(13) Uani 1 1 d . . . . .
H15A H 0.207847 0.309169 0.665870 0.155 Uiso 1 1 calc R U . . .
H15B H 0.183297 0.291729 0.581199 0.155 Uiso 1 1 calc R U . . .
H15C H 0.164578 0.452950 0.633151 0.155 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
S12 C11 1.831(3) . ?
S12 C13 1.764(3) . ?
O14 C13 1.199(4) . ?
N8 C9 1.380(4) . ?
N8 C7 1.370(4) . ?
N8 C19 1.464(3) . ?
C2 C1 1.425(4) . ?
C2 C3 1.398(4) . ?
C2 C7 1.413(4) . ?
C1 C9 1.366(4) . ?
C1 C10 1.496(4) . ?
C11 H11 0.9800 . ?
C11 C10 1.532(4) . ?
C11 C16 1.502(4) . ?
C9 C18 1.496(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 C6 1.389(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.289(5) . ?
C13 C15 1.496(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C5 H5 0.9300 . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S12 C11 100.89(13) . . ?
C9 N8 C19 125.6(3) . . ?
C7 N8 C9 109.1(2) . . ?
C7 N8 C19 125.2(3) . . ?
C3 C2 C1 134.5(3) . . ?
C3 C2 C7 118.6(3) . . ?
C7 C2 C1 106.9(2) . . ?
C2 C1 C10 125.1(2) . . ?
C9 C1 C2 107.2(2) . . ?
C9 C1 C10 127.6(2) . . ?
S12 C11 H11 108.5 . . ?
C10 C11 S12 109.79(19) . . ?
C10 C11 H11 108.5 . . ?
C16 C11 S12 107.66(18) . . ?
C16 C11 H11 108.5 . . ?
C16 C11 C10 113.8(2) . . ?
N8 C9 C18 121.1(3) . . ?
C1 C9 N8 109.3(3) . . ?
C1 C9 C18 129.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C1 C10 C11 114.1(2) . . ?
C1 C10 H10A 108.7 . . ?
C1 C10 H10B 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N8 C7 C2 107.5(2) . . ?
N8 C7 C6 130.6(3) . . ?
C6 C7 C2 121.8(3) . . ?
C11 C16 H16 117.6 . . ?
C17 C16 C11 124.8(3) . . ?
C17 C16 H16 117.6 . . ?
O14 C13 S12 122.7(3) . . ?
O14 C13 C15 123.9(3) . . ?
C15 C13 S12 113.4(3) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 C7 117.7(3) . . ?
C5 C6 H6 121.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N8 C19 H19A 109.5 . . ?
N8 C19 H19B 109.5 . . ?
N8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
S12 C11 C10 C1 170.64(19) . . . . ?
S12 C11 C16 C17 -101.6(4) . . . . ?
N8 C7 C6 C5 179.8(3) . . . . ?
C2 C1 C9 N8 0.4(3) . . . . ?
C2 C1 C9 C18 -179.3(3) . . . . ?
C2 C1 C10 C11 -74.1(4) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C2 C7 C6 C5 -0.9(5) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
C1 C2 C7 N8 -0.5(3) . . . . ?
C1 C2 C7 C6 -179.9(3) . . . . ?
C11 S12 C13 O14 -2.2(4) . . . . ?
C11 S12 C13 C15 177.8(3) . . . . ?
C9 N8 C7 C2 0.7(3) . . . . ?
C9 N8 C7 C6 -179.9(3) . . . . ?
C9 C1 C10 C11 109.8(3) . . . . ?
C3 C2 C1 C9 179.2(3) . . . . ?
C3 C2 C1 C10 2.5(5) . . . . ?
C3 C2 C7 N8 -179.8(3) . . . . ?
C3 C2 C7 C6 0.8(5) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C10 C1 C9 N8 177.0(3) . . . . ?
C10 C1 C9 C18 -2.6(5) . . . . ?
C10 C11 C16 C17 136.5(4) . . . . ?
C7 N8 C9 C1 -0.7(3) . . . . ?
C7 N8 C9 C18 179.0(3) . . . . ?
C7 C2 C1 C9 0.1(3) . . . . ?
C7 C2 C1 C10 -176.7(3) . . . . ?
C7 C2 C3 C4 0.1(5) . . . . ?
C7 C6 C5 C4 0.2(6) . . . . ?
C16 C11 C10 C1 -68.6(3) . . . . ?
C13 S12 C11 C10 -79.0(2) . . . . ?
C13 S12 C11 C16 156.7(2) . . . . ?
C19 N8 C9 C1 -178.0(3) . . . . ?
C19 N8 C9 C18 1.6(5) . . . . ?
C19 N8 C7 C2 178.1(3) . . . . ?
C19 N8 C7 C6 -2.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.885
####################################################################### 
# 
# 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_wht-2-20230309_auto
_database_code_depnum_ccdc_archive 'CCDC 2345332'
_audit_update_record             
;
2024-04-02 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-03-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N O2 S'
_chemical_formula_sum            'C14 H13 N O2 S'
_chemical_formula_weight         259.31
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 C1 H1 O1 N1'
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                   6.15030(10)
_cell_length_b                   10.23780(10)
_cell_length_c                   20.4571(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1288.09(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8728
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3170
_cell_measurement_theta_min      4.2800
_shelx_estimated_absorpt_T_max   0.670
_shelx_estimated_absorpt_T_min   0.561
_exptl_absorpt_coefficient_mu    2.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14435
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.406
_diffrn_reflns_theta_min         4.322
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  33.00   1.00    1.00    --  -35.62  -2.00 -98.00  138
  2  ω    -92.00  -9.00   1.00    1.00    --  -35.62 132.00-129.00   83
  3  ω     94.00 175.00   1.00    1.28    --  107.12 132.00-129.00   81
  4  ω     38.00 176.00   1.00    1.28    --  107.12  -2.00 -98.00  138
  5  ω     94.00 175.00   1.00    1.28    --  107.12 133.00 139.00   81
  6  ω      6.00  74.00   1.00    1.00    --   35.62 -99.00-150.00   68
  7  ω     40.00 125.00   1.00    1.28    --  107.12 -61.00 -60.00   85
  8  ω     40.00 109.00   1.00    1.28    --  107.12-111.00-150.00   69
  9  ω     38.00 106.00   1.00    1.28    --  107.12 -95.00  90.00   68
 10  ω     40.00 125.00   1.00    1.28    --  107.12 -61.00  30.00   85
 11  ω    104.00 174.00   1.00    1.28    --  107.12 111.00-120.00   70
 12  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00-150.00   84
 13  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00  90.00   84
 14  ω     61.00 108.00   1.00    1.00    --   35.62 178.00 150.00   47
 15  ω     40.00 125.00   1.00    1.28    --  107.12 -61.00-180.00   85
 16  ω     86.00 177.00   1.00    1.28    --  107.12  30.00 -30.00   91
 17  ω     40.00 109.00   1.00    1.28    --  107.12-111.00 -30.00   69
 18  ω     90.00 176.00   1.00    1.28    --  107.12  45.00 120.00   86
 19  ω     90.00 176.00   1.00    1.28    --  107.12  45.00   0.00   86
 20  ω     38.00 176.00   1.00    1.28    --  107.12   0.00 120.00  138
 21  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00-120.00   88
 22  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00 150.00   84
 23  ω     19.00 103.00   1.00    1.00    --   35.62  57.00  60.00   84
 24  ω     89.00 174.00   1.00    1.28    --  107.12  61.00  30.00   85
 25  ω     86.00 177.00   1.00    1.28    --  107.12  30.00-180.00   91
 26  ω     86.00 127.00   1.00    1.28    --  107.12  30.00-120.00   41
 27  ω     86.00 177.00   1.00    1.28    --  107.12  30.00 -60.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0056847000
_diffrn_orient_matrix_UB_12      0.1446404000
_diffrn_orient_matrix_UB_13      -0.0207489000
_diffrn_orient_matrix_UB_21      0.0002839000
_diffrn_orient_matrix_UB_22      0.0414485000
_diffrn_orient_matrix_UB_23      0.0724068000
_diffrn_orient_matrix_UB_31      0.2503347000
_diffrn_orient_matrix_UB_32      0.0032762000
_diffrn_orient_matrix_UB_33      -0.0005352000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2429
_reflns_number_total             2498
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 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         0.211
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.094
_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)+(0.0462P)²+0.2075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0901
_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:
 C00C(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00D(H00E), C00E(H00F), C00F(H00G), C00H(H00K)
2.d X=CH2 refined with riding coordinates:
 C00I(H00L,H00M)
2.e Idealised Me refined as rotating group:
 C00G(H00H,H00I,H00J)
;
_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
S001 S 0.25847(13) 0.34560(6) 0.52818(4) 0.0567(2) Uani 1 1 d . . . . .
O002 O -0.1675(3) 0.67431(19) 0.57793(10) 0.0535(5) Uani 1 1 d . . . . .
O23 O -0.0637(3) 0.36754(18) 0.61164(10) 0.0545(5) Uani 1 1 d . . . . .
N004 N -0.0045(3) 0.6936(2) 0.67869(10) 0.0407(5) Uani 1 1 d . . . . .
C005 C 0.2901(4) 0.5584(2) 0.66762(10) 0.0316(5) Uani 1 1 d . . . . .
C006 C 0.1709(4) 0.5579(2) 0.60268(11) 0.0312(5) Uani 1 1 d . . . . .
C007 C 0.1777(4) 0.6409(2) 0.71020(11) 0.0358(5) Uani 1 1 d . . . . .
C008 C -0.0233(4) 0.6474(2) 0.61634(11) 0.0371(5) Uani 1 1 d . . . . .
C009 C 0.0910(4) 0.4196(2) 0.58669(12) 0.0368(5) Uani 1 1 d . . . . .
C00A C 0.3021(4) 0.6038(2) 0.54356(11) 0.0364(5) Uani 1 1 d . . . . .
H00A H 0.399554 0.673764 0.556317 0.044 Uiso 1 1 calc R U . . .
H00B H 0.204828 0.636735 0.510069 0.044 Uiso 1 1 calc R U . . .
C00B C 0.4736(4) 0.4942(2) 0.68855(11) 0.0397(5) Uani 1 1 d . . . . .
H00C H 0.549114 0.438754 0.660579 0.048 Uiso 1 1 calc R U . . .
C00C C 0.4333(4) 0.4882(2) 0.51679(11) 0.0391(5) Uani 1 1 d . . . . .
H00D H 0.566583 0.477540 0.542499 0.047 Uiso 1 1 calc R U . . .
C00D C 0.2483(5) 0.6616(2) 0.77391(12) 0.0478(6) Uani 1 1 d . . . . .
H00E H 0.173902 0.717270 0.802008 0.057 Uiso 1 1 calc R U . . .
C00E C 0.5443(5) 0.5138(3) 0.75253(13) 0.0502(6) Uani 1 1 d . . . . .
H00F H 0.667911 0.470846 0.767460 0.060 Uiso 1 1 calc R U . . .
C00F C 0.4330(5) 0.5963(3) 0.79386(13) 0.0524(7) Uani 1 1 d . . . . .
H00G H 0.483615 0.608231 0.836276 0.063 Uiso 1 1 calc R U . . .
C00G C -0.1533(5) 0.7867(3) 0.70767(17) 0.0572(8) Uani 1 1 d . . . . .
H00H H -0.198086 0.755814 0.749886 0.086 Uiso 1 1 calc R U . . .
H00I H -0.278467 0.796272 0.680040 0.086 Uiso 1 1 calc R U . . .
H00J H -0.082054 0.869580 0.712283 0.086 Uiso 1 1 calc R U . . .
C00H C 0.4902(6) 0.5046(3) 0.44624(13) 0.0581(8) Uani 1 1 d . . . . .
H00K H 0.377037 0.505863 0.416110 0.070 Uiso 1 1 calc R U . . .
C00I C 0.6845(7) 0.5170(4) 0.42447(17) 0.0889(13) Uani 1 1 d . . . . .
H00L H 0.801451 0.516123 0.453275 0.107 Uiso 1 1 calc R U . . .
H00M H 0.708498 0.526841 0.379856 0.107 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
S001 C009 1.751(2) . ?
S001 C00C 1.828(3) . ?
O002 C008 1.216(3) . ?
O23 C009 1.204(3) . ?
N004 C007 1.401(3) . ?
N004 C008 1.366(3) . ?
N004 C00G 1.448(3) . ?
C005 C006 1.517(3) . ?
C005 C007 1.397(3) . ?
C005 C00B 1.374(3) . ?
C006 C008 1.531(3) . ?
C006 C009 1.534(3) . ?
C006 C00A 1.528(3) . ?
C007 C00D 1.390(3) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00C 1.534(3) . ?
C00B H00C 0.9300 . ?
C00B C00E 1.394(3) . ?
C00C H00D 0.9800 . ?
C00C C00H 1.495(3) . ?
C00D H00E 0.9300 . ?
C00D C00F 1.380(4) . ?
C00E H00F 0.9300 . ?
C00E C00F 1.377(4) . ?
C00F H00G 0.9300 . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00G H00J 0.9600 . ?
C00H H00K 0.9300 . ?
C00H C00I 1.281(5) . ?
C00I H00L 0.9300 . ?
C00I H00M 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
C009 S001 C00C 95.02(11) . . ?
C007 N004 C00G 124.8(2) . . ?
C008 N004 C007 111.35(19) . . ?
C008 N004 C00G 123.8(2) . . ?
C007 C005 C006 107.97(19) . . ?
C00B C005 C006 131.9(2) . . ?
C00B C005 C007 120.1(2) . . ?
C005 C006 C008 102.44(18) . . ?
C005 C006 C009 110.12(18) . . ?
C005 C006 C00A 115.91(19) . . ?
C008 C006 C009 109.95(19) . . ?
C00A C006 C008 111.88(18) . . ?
C00A C006 C009 106.50(18) . . ?
C005 C007 N004 110.0(2) . . ?
C00D C007 N004 128.5(2) . . ?
C00D C007 C005 121.5(2) . . ?
O002 C008 N004 125.9(2) . . ?
O002 C008 C006 125.9(2) . . ?
N004 C008 C006 108.2(2) . . ?
O23 C009 S001 124.2(2) . . ?
O23 C009 C006 124.8(2) . . ?
C006 C009 S001 110.90(16) . . ?
C006 C00A H00A 109.9 . . ?
C006 C00A H00B 109.9 . . ?
C006 C00A C00C 108.87(18) . . ?
H00A C00A H00B 108.3 . . ?
C00C C00A H00A 109.9 . . ?
C00C C00A H00B 109.9 . . ?
C005 C00B H00C 120.7 . . ?
C005 C00B C00E 118.7(2) . . ?
C00E C00B H00C 120.7 . . ?
S001 C00C H00D 109.6 . . ?
C00A C00C S001 105.14(16) . . ?
C00A C00C H00D 109.6 . . ?
C00H C00C S001 110.5(2) . . ?
C00H C00C C00A 112.4(2) . . ?
C00H C00C H00D 109.6 . . ?
C007 C00D H00E 121.3 . . ?
C00F C00D C007 117.4(2) . . ?
C00F C00D H00E 121.3 . . ?
C00B C00E H00F 119.7 . . ?
C00F C00E C00B 120.7(3) . . ?
C00F C00E H00F 119.7 . . ?
C00D C00F H00G 119.2 . . ?
C00E C00F C00D 121.7(2) . . ?
C00E C00F H00G 119.2 . . ?
N004 C00G H00H 109.5 . . ?
N004 C00G H00I 109.5 . . ?
N004 C00G H00J 109.5 . . ?
H00H C00G H00I 109.5 . . ?
H00H C00G H00J 109.5 . . ?
H00I C00G H00J 109.5 . . ?
C00C C00H H00K 117.8 . . ?
C00I C00H C00C 124.4(3) . . ?
C00I C00H H00K 117.8 . . ?
C00H C00I H00L 120.0 . . ?
C00H C00I H00M 120.0 . . ?
H00L C00I H00M 120.0 . . ?

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
S001 C00C C00H C00I -127.8(4) . . . . ?
N004 C007 C00D C00F 179.2(2) . . . . ?
C005 C006 C008 O002 -178.7(2) . . . . ?
C005 C006 C008 N004 2.5(2) . . . . ?
C005 C006 C009 S001 -102.69(19) . . . . ?
C005 C006 C009 O23 76.1(3) . . . . ?
C005 C006 C00A C00C 84.6(2) . . . . ?
C005 C007 C00D C00F -0.6(4) . . . . ?
C005 C00B C00E C00F -0.2(4) . . . . ?
C006 C005 C007 N004 0.3(3) . . . . ?
C006 C005 C007 C00D -179.9(2) . . . . ?
C006 C005 C00B C00E -179.5(2) . . . . ?
C006 C00A C00C S001 35.7(2) . . . . ?
C006 C00A C00C C00H 156.0(2) . . . . ?
C007 N004 C008 O002 178.6(2) . . . . ?
C007 N004 C008 C006 -2.5(3) . . . . ?
C007 C005 C006 C008 -1.6(2) . . . . ?
C007 C005 C006 C009 -118.5(2) . . . . ?
C007 C005 C006 C00A 120.5(2) . . . . ?
C007 C005 C00B C00E -0.3(4) . . . . ?
C007 C00D C00F C00E 0.1(4) . . . . ?
C008 N004 C007 C005 1.5(3) . . . . ?
C008 N004 C007 C00D -178.4(2) . . . . ?
C008 C006 C009 S001 145.15(16) . . . . ?
C008 C006 C009 O23 -36.0(3) . . . . ?
C008 C006 C00A C00C -158.5(2) . . . . ?
C009 S001 C00C C00A -18.81(18) . . . . ?
C009 S001 C00C C00H -140.4(2) . . . . ?
C009 C006 C008 O002 -61.6(3) . . . . ?
C009 C006 C008 N004 119.5(2) . . . . ?
C009 C006 C00A C00C -38.3(3) . . . . ?
C00A C006 C008 O002 56.5(3) . . . . ?
C00A C006 C008 N004 -122.3(2) . . . . ?
C00A C006 C009 S001 23.7(2) . . . . ?
C00A C006 C009 O23 -157.4(2) . . . . ?
C00A C00C C00H C00I 115.0(4) . . . . ?
C00B C005 C006 C008 177.6(2) . . . . ?
C00B C005 C006 C009 60.7(3) . . . . ?
C00B C005 C006 C00A -60.2(3) . . . . ?
C00B C005 C007 N004 -179.1(2) . . . . ?
C00B C005 C007 C00D 0.7(3) . . . . ?
C00B C00E C00F C00D 0.3(4) . . . . ?
C00C S001 C009 O23 178.4(2) . . . . ?
C00C S001 C009 C006 -2.77(18) . . . . ?
C00G N004 C007 C005 -177.8(2) . . . . ?
C00G N004 C007 C00D 2.4(4) . . . . ?
C00G N004 C008 O002 -2.1(4) . . . . ?
C00G N004 C008 C006 176.7(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 2.028
_oxdiff_exptl_absorpt_empirical_full_min 0.571
####################################################################### 
# 
# 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_wht-20231024_auto
_database_code_depnum_ccdc_archive 'CCDC 2345333'
_audit_update_record             
;
2024-04-02 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-10-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N2 O2 S'
_chemical_formula_sum            'C15 H13 N2 O2 S'
_chemical_formula_weight         285.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3006(4)
_cell_length_b                   9.5212(7)
_cell_length_c                   11.2656(7)
_cell_angle_alpha                68.188(6)
_cell_angle_beta                 73.641(5)
_cell_angle_gamma                87.454(5)
_cell_volume                     695.99(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3385
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3300
_cell_measurement_theta_min      4.4180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             298
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4971
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.353
_diffrn_reflns_theta_min         4.411
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00 -56.00   1.00    1.00    --  -35.62-156.00 153.00   26
  2  ω    -28.00  -2.00   1.00    1.00    --  -35.62 120.00  33.00   26
  3  ω    -89.00 -64.00   1.00    1.00    --  -35.62 156.00-169.00   25
  4  ω     51.00  77.00   1.00    1.00    --   35.62-120.00 -50.00   26
  5  ω     74.00 106.00   1.00    1.00    --   35.62-156.00 153.00   32
  6  ω    101.00 133.00   1.00    1.00    --  106.81 120.00  33.00   32
  7  ω    100.00 131.00   1.00    1.00    --  106.81 156.00-169.00   31
  8  ω     64.00  89.00   1.00    1.00    --  106.81-156.00 153.00   25
  9  ω     49.00 109.00   1.00    1.00    --  106.81-120.00 -50.00   60
 10  ω    -74.00 -17.00   1.00    1.00    --  -35.62 -38.00 -90.00   57
 11  ω    -59.00 -29.00   1.00    1.00    --  -35.62  77.00-180.00   30
 12  ω   -103.00 -22.00   1.00    1.00    --  -35.62 -57.00 150.00   81
 13  ω     -1.00  24.00   1.00    1.00    --  -35.62  77.00-180.00   25
 14  ω   -102.00 -76.00   1.00    1.00    --  -35.62 -38.00 -90.00   26
 15  ω    -92.00 -40.00   1.00    1.00    --  -35.62-178.00 150.00   52
 16  ω    -34.00  55.00   1.00    1.00    --   35.62 -38.00   0.00   89
 17  ω     77.00 103.00   1.00    1.00    --   35.62 178.00  90.00   26
 18  ω     62.00  87.00   1.00    1.00    --   35.62 178.00-150.00   25
 19  ω    103.00 163.00   1.00    1.00    --  106.81  77.00  90.00   60
 20  ω     38.00 106.00   1.00    1.00    --  106.81 -95.00 120.00   68
 21  ω     48.00 106.00   1.00    1.00    --  106.81 -61.00 -90.00   58
 22  ω     42.00 108.00   1.00    1.00    --  106.81-111.00  30.00   66
 23  ω    100.00 126.00   1.00    1.00    --  106.81  61.00 -30.00   26
 24  ω     46.00  72.00   1.00    1.00    --  106.81-111.00-150.00   26
 25  ω     74.00 118.00   1.00    1.00    --  106.81 178.00   0.00   44
 26  ω     41.00 108.00   1.00    1.00    --  106.81-111.00  60.00   67
 27  ω     44.00  96.00   1.00    1.00    --  106.81-111.00-120.00   52
 28  ω    129.00 156.00   1.00    1.00    --  106.81  61.00 -30.00   27
 29  ω    103.00 174.00   1.00    1.00    --  106.81  77.00-180.00   71
 30  ω     91.00 175.00   1.00    1.00    --  106.81  45.00-120.00   84
 31  ω     54.00 125.00   1.00    1.00    --  106.81 -61.00  90.00   71
 32  ω     68.00 164.00   1.00    1.00    --  106.81  15.00-180.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0426894000
_diffrn_orient_matrix_UB_12      -0.0874790000
_diffrn_orient_matrix_UB_13      0.1515849000
_diffrn_orient_matrix_UB_21      -0.0226603000
_diffrn_orient_matrix_UB_22      -0.1497276000
_diffrn_orient_matrix_UB_23      -0.0190110000
_diffrn_orient_matrix_UB_31      0.2150637000
_diffrn_orient_matrix_UB_32      -0.0210353000
_diffrn_orient_matrix_UB_33      -0.0169519000
_diffrn_oxdiff_digest_frames     
;
01a3efcddcdc015894a898715e99f30c28000284341
;
_diffrn_oxdiff_digest_hkl        
;
015924a307cb831d4137b0a0b69d96b13b6016
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2423
_reflns_number_total             2622
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0782P)²+0.3631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1418
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C15(H15)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), 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
S13 S 0.53405(8) 0.19702(7) 0.58711(5) 0.0449(2) Uani 1 1 d . . . . .
O19 O 0.8423(2) 0.05858(17) 0.34730(15) 0.0424(4) Uani 1 1 d . . . . .
O17 O 0.6143(3) 0.81331(17) 0.00625(16) 0.0448(4) Uani 1 1 d . . . . .
N9 N 0.8082(2) 0.22003(19) 0.14558(17) 0.0311(4) Uani 1 1 d . . . . .
C3 C 0.7037(3) 0.4299(2) 0.19062(18) 0.0276(4) Uani 1 1 d . . . . .
N14 N 0.3709(3) 0.2329(3) 0.3895(2) 0.0532(6) Uani 1 1 d . . . . .
C8 C 0.7613(3) 0.3717(2) 0.09041(19) 0.0277(4) Uani 1 1 d . . . . .
C1 C 0.7964(3) 0.1786(2) 0.27659(19) 0.0302(4) Uani 1 1 d . . . . .
C4 C 0.6562(3) 0.5783(2) 0.1605(2) 0.0321(4) Uani 1 1 d . . . . .
H4 H 0.619035 0.618520 0.226695 0.039 Uiso 1 1 calc R . . . .
C2 C 0.7142(3) 0.3096(2) 0.32060(18) 0.0282(4) Uani 1 1 d . . . . .
C10 C 0.5176(3) 0.2480(2) 0.42289(19) 0.0328(4) Uani 1 1 d . . . . .
C11 C 0.8357(3) 0.3562(2) 0.3921(2) 0.0338(5) Uani 1 1 d . . . . .
H11A H 0.808068 0.457504 0.390186 0.041 Uiso 1 1 calc R . . . .
H11B H 0.970317 0.357476 0.346719 0.041 Uiso 1 1 calc R . . . .
C5 C 0.6654(3) 0.6670(2) 0.0280(2) 0.0324(4) Uani 1 1 d . . . . .
C12 C 0.7917(3) 0.2443(2) 0.5367(2) 0.0339(5) Uani 1 1 d . . . . .
H12 H 0.860819 0.152860 0.540143 0.041 Uiso 1 1 calc R . . . .
C6 C 0.7209(3) 0.6077(2) -0.0708(2) 0.0343(5) Uani 1 1 d . . . . .
H6 H 0.725567 0.668125 -0.158287 0.041 Uiso 1 1 calc R . . . .
C7 C 0.7699(3) 0.4578(2) -0.0396(2) 0.0336(5) Uani 1 1 d . . . . .
H7 H 0.807567 0.417031 -0.105374 0.040 Uiso 1 1 calc R . . . .
C15 C 0.8441(3) 0.3117(2) 0.6244(2) 0.0377(5) Uani 1 1 d . . . . .
H15 H 0.784815 0.397474 0.632455 0.045 Uiso 1 1 calc R . . . .
C16 C 0.9706(4) 0.2553(3) 0.6911(2) 0.0413(5) Uani 1 1 d . . . . .
C20 C 0.8736(4) 0.1247(3) 0.0690(2) 0.0408(5) Uani 1 1 d . . . . .
H20A H 0.790604 0.130516 0.014961 0.061 Uiso 1 1 calc GR . . . .
H20B H 0.871912 0.021669 0.128800 0.061 Uiso 1 1 calc GR . . . .
H20C H 1.001648 0.158931 0.012704 0.061 Uiso 1 1 calc GR . . . .
C18 C 0.6367(4) 0.9120(3) -0.1289(2) 0.0456(6) Uani 1 1 d . . . . .
H18A H 0.767460 0.916673 -0.180326 0.068 Uiso 1 1 calc GR . . . .
H18B H 0.602842 1.011621 -0.132085 0.068 Uiso 1 1 calc GR . . . .
H18C H 0.554937 0.873962 -0.165231 0.068 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S13 C10 1.768(2) . ?
S13 C12 1.830(2) . ?
O19 C1 1.222(2) . ?
O17 C5 1.376(2) . ?
O17 C18 1.428(3) . ?
N9 C8 1.413(2) . ?
N9 C1 1.356(3) . ?
N9 C20 1.451(3) . ?
C3 C8 1.391(3) . ?
C3 C4 1.378(3) . ?
C3 C2 1.507(2) . ?
N14 C10 1.261(3) . ?
C8 C7 1.372(3) . ?
C1 C2 1.545(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(3) . ?
C2 C10 1.540(3) . ?
C2 C11 1.528(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.529(3) . ?
C5 C6 1.383(3) . ?
C12 H12 0.9800 . ?
C12 C15 1.497(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(3) . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.324(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S13 C12 95.15(9) . . ?
C5 O17 C18 116.94(18) . . ?
C8 N9 C20 124.00(17) . . ?
C1 N9 C8 111.45(16) . . ?
C1 N9 C20 124.42(17) . . ?
C8 C3 C2 108.99(16) . . ?
C4 C3 C8 120.20(18) . . ?
C4 C3 C2 130.75(18) . . ?
C3 C8 N9 109.29(16) . . ?
C7 C8 N9 128.97(18) . . ?
C7 C8 C3 121.74(18) . . ?
O19 C1 N9 125.94(19) . . ?
O19 C1 C2 126.07(18) . . ?
N9 C1 C2 107.99(16) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.36(19) . . ?
C5 C4 H4 120.8 . . ?
C3 C2 C1 101.95(15) . . ?
C3 C2 C10 113.99(16) . . ?
C3 C2 C11 115.12(16) . . ?
C10 C2 C1 106.29(16) . . ?
C11 C2 C1 112.44(16) . . ?
C11 C2 C10 106.79(16) . . ?
N14 C10 S13 126.74(17) . . ?
N14 C10 C2 122.73(18) . . ?
C2 C10 S13 110.47(14) . . ?
C2 C11 H11A 109.7 . . ?
C2 C11 H11B 109.7 . . ?
C2 C11 C12 109.75(16) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
O17 C5 C4 114.86(18) . . ?
O17 C5 C6 124.09(19) . . ?
C6 C5 C4 121.05(19) . . ?
S13 C12 H12 109.6 . . ?
C11 C12 S13 104.33(14) . . ?
C11 C12 H12 109.6 . . ?
C15 C12 S13 111.42(15) . . ?
C15 C12 C11 112.05(17) . . ?
C15 C12 H12 109.6 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.18(19) . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 118.47(19) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C12 C15 H15 118.3 . . ?
C16 C15 C12 123.3(2) . . ?
C16 C15 H15 118.3 . . ?
N9 C20 H20A 109.5 . . ?
N9 C20 H20B 109.5 . . ?
N9 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
O17 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
S13 C12 C15 C16 123.7(2) . . . . ?
O19 C1 C2 C3 174.9(2) . . . . ?
O19 C1 C2 C10 -65.5(3) . . . . ?
O19 C1 C2 C11 51.0(3) . . . . ?
O17 C5 C6 C7 -179.84(19) . . . . ?
N9 C8 C7 C6 -178.14(19) . . . . ?
N9 C1 C2 C3 -5.3(2) . . . . ?
N9 C1 C2 C10 114.39(18) . . . . ?
N9 C1 C2 C11 -129.11(17) . . . . ?
C3 C8 C7 C6 0.6(3) . . . . ?
C3 C4 C5 O17 179.46(18) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C3 C2 C10 S13 -147.63(14) . . . . ?
C3 C2 C10 N14 34.7(3) . . . . ?
C3 C2 C11 C12 164.62(17) . . . . ?
C8 N9 C1 O19 -174.22(19) . . . . ?
C8 N9 C1 C2 5.9(2) . . . . ?
C8 C3 C4 C5 0.8(3) . . . . ?
C8 C3 C2 C1 2.9(2) . . . . ?
C8 C3 C2 C10 -111.21(19) . . . . ?
C8 C3 C2 C11 124.88(19) . . . . ?
C1 N9 C8 C3 -4.1(2) . . . . ?
C1 N9 C8 C7 174.7(2) . . . . ?
C1 C2 C10 S13 100.88(16) . . . . ?
C1 C2 C10 N14 -76.7(3) . . . . ?
C1 C2 C11 C12 -79.2(2) . . . . ?
C4 C3 C8 N9 177.93(17) . . . . ?
C4 C3 C8 C7 -1.0(3) . . . . ?
C4 C3 C2 C1 -174.3(2) . . . . ?
C4 C3 C2 C10 71.6(3) . . . . ?
C4 C3 C2 C11 -52.3(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C2 C3 C8 N9 0.4(2) . . . . ?
C2 C3 C8 C7 -178.57(18) . . . . ?
C2 C3 C4 C5 177.69(19) . . . . ?
C2 C11 C12 S13 -37.41(19) . . . . ?
C2 C11 C12 C15 -158.08(18) . . . . ?
C10 S13 C12 C11 22.19(15) . . . . ?
C10 S13 C12 C15 143.28(15) . . . . ?
C10 C2 C11 C12 37.0(2) . . . . ?
C11 C2 C10 S13 -19.35(19) . . . . ?
C11 C2 C10 N14 163.0(2) . . . . ?
C11 C12 C15 C16 -119.8(2) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C12 S13 C10 N14 175.7(2) . . . . ?
C12 S13 C10 C2 -1.84(16) . . . . ?
C20 N9 C8 C3 179.89(19) . . . . ?
C20 N9 C8 C7 -1.3(3) . . . . ?
C20 N9 C1 O19 1.8(3) . . . . ?
C20 N9 C1 C2 -178.10(19) . . . . ?
C18 O17 C5 C4 174.86(19) . . . . ?
C18 O17 C5 C6 -5.6(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 1.549
_oxdiff_exptl_absorpt_empirical_full_min 0.632
####################################################################### 
# 
# 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_wht-20230427_auto
_database_code_depnum_ccdc_archive 'CCDC 2345468'
_audit_update_record             
;
2024-04-03 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2024-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N2 O S'
_chemical_formula_sum            'C14 H14 N2 O S'
_chemical_formula_weight         258.33
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N1 C1 O1 H1'
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                   6.19080(10)
_cell_length_b                   12.5894(2)
_cell_length_c                   16.8912(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1316.47(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5270
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4880
_cell_measurement_theta_min      4.3700
_shelx_estimated_absorpt_T_max   0.572
_shelx_estimated_absorpt_T_min   0.421
_exptl_absorpt_coefficient_mu    2.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.472
_diffrn_reflns_theta_min         4.380
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -50.00   1.00    1.00    --  -35.62-178.00 120.00   36
  2  ω   -101.00 -20.00   1.00    1.00    --  -35.62 -57.00 120.00   81
  3  ω    -96.00  -6.00   1.00    1.00    --  -35.62 -19.00-120.00   90
  4  ω    -65.00  35.00   1.00    1.00    --  -35.62  19.00  90.00  100
  5  ω     23.00  62.00   1.00    1.00    --   35.62 -99.00 -30.00   39
  6  ω     25.00  73.00   1.00    1.00    --   35.62 -99.00  60.00   48
  7  ω     29.00  65.00   1.00    1.00    --   35.62 -99.00-120.00   36
  8  ω     61.00 108.00   1.00    1.32    --  107.12-111.00-180.00   47
  9  ω    110.00 173.00   1.00    1.32    --  107.12 111.00  90.00   63
 10  ω     41.00 109.00   1.00    1.32    --  107.12-111.00  60.00   68
 11  ω     58.00 109.00   1.00    1.32    --  107.12-111.00 -60.00   51
 12  ω    117.00 142.00   1.00    1.32    --  107.12 -15.00 -60.00   25
 13  ω     43.00  69.00   1.00    1.32    --  107.12 -45.00-120.00   26
 14  ω     91.00 121.00   1.00    1.32    --  107.12 -45.00-120.00   30
 15  ω     46.00  98.00   1.00    1.32    --  107.12 -15.00 -60.00   52
 16  ω    104.00 175.00   1.00    1.32    --  107.12  77.00-150.00   71
 17  ω     75.00 106.00   1.00    1.32    --  107.12 -95.00-180.00   31
 18  ω     42.00 124.00   1.00    1.32    --  107.12 -45.00  60.00   82
 19  ω    112.00 138.00   1.00    1.32    --  107.12 111.00 150.00   26
 20  ω     93.00 145.00   1.00    1.32    --  107.12  61.00 -90.00   52
 21  ω     52.00  95.00   1.00    1.32    --  107.12 -95.00  90.00   43
 22  ω    105.00 130.00   1.00    1.32    --  107.12 111.00 -30.00   25
 23  ω     98.00 171.00   1.00    1.32    --  107.12  30.00 150.00   73
 24  ω     42.00 118.00   1.00    1.32    --  107.12 -45.00 150.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1048581000
_diffrn_orient_matrix_UB_12      -0.0301268000
_diffrn_orient_matrix_UB_13      0.0796381000
_diffrn_orient_matrix_UB_21      -0.0904180000
_diffrn_orient_matrix_UB_22      0.1135119000
_diffrn_orient_matrix_UB_23      0.0079175000
_diffrn_orient_matrix_UB_31      -0.2066196000
_diffrn_orient_matrix_UB_32      -0.0343709000
_diffrn_orient_matrix_UB_33      -0.0438426000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2407
_reflns_number_total             2529
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 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         0.155
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 933 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.066
_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)+(0.0510P)²+0.1965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0937
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C15(H15), C3(H3), C4(H4)
2.d X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_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
S13 S 0.53513(12) 0.80490(5) 0.19794(5) 0.0486(2) Uani 1 1 d . . . . .
O17 O 0.9709(4) 0.52759(16) 0.24271(13) 0.0503(5) Uani 1 1 d . . . . .
N9 N 0.8533(4) 0.52786(17) 0.37143(14) 0.0402(5) Uani 1 1 d . . . . .
N14 N 0.9006(4) 0.78340(19) 0.28708(15) 0.0432(5) Uani 1 1 d . . . . .
C7 C 0.6522(4) 0.63191(18) 0.28257(14) 0.0324(5) Uani 1 1 d . . . . .
C6 C 0.5505(4) 0.63265(19) 0.36436(14) 0.0341(5) Uani 1 1 d . . . . .
C8 C 0.8471(4) 0.55727(19) 0.29397(16) 0.0362(5) Uani 1 1 d . . . . .
C10 C 0.7282(4) 0.74428(19) 0.26107(15) 0.0330(5) Uani 1 1 d . . . . .
C1 C 0.6784(5) 0.5703(2) 0.41375(16) 0.0397(6) Uani 1 1 d . . . . .
C12 C 0.3706(4) 0.6859(2) 0.18438(15) 0.0380(5) Uani 1 1 d . . . . .
H12 H 0.238849 0.690936 0.216341 0.046 Uiso 1 1 calc R U . . .
C11 C 0.5113(4) 0.59389(19) 0.21413(16) 0.0386(6) Uani 1 1 d . . . . .
H11A H 0.420061 0.535864 0.231689 0.046 Uiso 1 1 calc R U . . .
H11B H 0.602002 0.568111 0.171418 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3707(5) 0.6829(2) 0.39393(17) 0.0446(6) Uani 1 1 d . . . . .
H5 H 0.285039 0.725396 0.361658 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6296(6) 0.5560(3) 0.49291(18) 0.0542(8) Uani 1 1 d . . . . .
H2 H 0.715829 0.514344 0.525548 0.065 Uiso 1 1 calc R U . . .
C15 C 0.3131(6) 0.6748(3) 0.09848(18) 0.0529(8) Uani 1 1 d . . . . .
H15 H 0.427153 0.672113 0.062681 0.063 Uiso 1 1 calc R U . . .
C18 C 1.0131(6) 0.4554(2) 0.4033(2) 0.0584(9) Uani 1 1 d . . . . .
H18A H 0.953271 0.385089 0.405780 0.088 Uiso 1 1 calc R U . . .
H18B H 1.053755 0.477925 0.455478 0.088 Uiso 1 1 calc R U . . .
H18C H 1.138137 0.455033 0.369651 0.088 Uiso 1 1 calc R U . . .
C3 C 0.4476(7) 0.6063(3) 0.52145(19) 0.0623(9) Uani 1 1 d . . . . .
H3 H 0.410357 0.597803 0.574414 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3201(6) 0.6683(3) 0.4739(2) 0.0580(9) Uani 1 1 d . . . . .
H4 H 0.198482 0.701084 0.495002 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1225(8) 0.6689(3) 0.0698(2) 0.0721(11) Uani 1 1 d . . . . .
H16A H 0.003340 0.671265 0.103295 0.087 Uiso 1 1 calc R U . . .
H16B H 0.102868 0.662131 0.015447 0.087 Uiso 1 1 calc R U . . .
H14 H 0.920(6) 0.841(3) 0.268(2) 0.059(11) Uiso 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
S13 C10 1.774(3) . ?
S13 C12 1.827(3) . ?
O17 C8 1.215(3) . ?
N9 C8 1.360(3) . ?
N9 C1 1.403(4) . ?
N9 C18 1.449(3) . ?
N14 C10 1.255(3) . ?
N14 H14 0.81(4) . ?
C7 C6 1.518(3) . ?
C7 C8 1.541(3) . ?
C7 C10 1.534(3) . ?
C7 C11 1.525(4) . ?
C6 C1 1.393(4) . ?
C6 C5 1.374(4) . ?
C1 C2 1.383(4) . ?
C12 H12 0.9800 . ?
C12 C11 1.534(4) . ?
C12 C15 1.500(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.398(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.278(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.371(5) . ?
C4 H4 0.9300 . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S13 C12 95.64(12) . . ?
C8 N9 C1 111.4(2) . . ?
C8 N9 C18 123.2(3) . . ?
C1 N9 C18 125.3(2) . . ?
C10 N14 H14 110(3) . . ?
C6 C7 C8 102.4(2) . . ?
C6 C7 C10 109.69(19) . . ?
C6 C7 C11 117.0(2) . . ?
C10 C7 C8 110.6(2) . . ?
C11 C7 C8 110.6(2) . . ?
C11 C7 C10 106.6(2) . . ?
C1 C6 C7 107.8(2) . . ?
C5 C6 C7 132.0(2) . . ?
C5 C6 C1 120.2(2) . . ?
O17 C8 N9 125.7(3) . . ?
O17 C8 C7 126.3(2) . . ?
N9 C8 C7 108.0(2) . . ?
N14 C10 S13 127.9(2) . . ?
N14 C10 C7 122.7(2) . . ?
C7 C10 S13 109.41(18) . . ?
C6 C1 N9 110.4(2) . . ?
C2 C1 N9 127.8(3) . . ?
C2 C1 C6 121.8(3) . . ?
S13 C12 H12 110.0 . . ?
C11 C12 S13 105.15(18) . . ?
C11 C12 H12 110.0 . . ?
C15 C12 S13 109.2(2) . . ?
C15 C12 H12 110.0 . . ?
C15 C12 C11 112.4(2) . . ?
C7 C11 C12 109.66(19) . . ?
C7 C11 H11A 109.7 . . ?
C7 C11 H11B 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C6 C5 H5 120.9 . . ?
C6 C5 C4 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C12 C15 H15 116.9 . . ?
C16 C15 C12 126.2(4) . . ?
C16 C15 H15 116.9 . . ?
N9 C18 H18A 109.5 . . ?
N9 C18 H18B 109.5 . . ?
N9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?

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
S13 C12 C11 C7 33.3(2) . . . . ?
S13 C12 C15 C16 -123.1(4) . . . . ?
N9 C1 C2 C3 180.0(3) . . . . ?
C7 C6 C1 N9 -0.7(3) . . . . ?
C7 C6 C1 C2 179.2(3) . . . . ?
C7 C6 C5 C4 -179.2(3) . . . . ?
C6 C7 C8 O17 175.5(3) . . . . ?
C6 C7 C8 N9 -2.9(3) . . . . ?
C6 C7 C10 S13 -99.9(2) . . . . ?
C6 C7 C10 N14 79.1(3) . . . . ?
C6 C7 C11 C12 83.5(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C6 C5 C4 C3 0.5(5) . . . . ?
C8 N9 C1 C6 -1.3(3) . . . . ?
C8 N9 C1 C2 178.8(3) . . . . ?
C8 C7 C6 C1 2.1(3) . . . . ?
C8 C7 C6 C5 -179.4(3) . . . . ?
C8 C7 C10 S13 147.87(17) . . . . ?
C8 C7 C10 N14 -33.1(3) . . . . ?
C8 C7 C11 C12 -159.8(2) . . . . ?
C10 S13 C12 C11 -14.50(19) . . . . ?
C10 S13 C12 C15 -135.4(2) . . . . ?
C10 C7 C6 C1 -115.4(2) . . . . ?
C10 C7 C6 C5 63.2(4) . . . . ?
C10 C7 C8 O17 -67.7(3) . . . . ?
C10 C7 C8 N9 114.0(2) . . . . ?
C10 C7 C11 C12 -39.6(3) . . . . ?
C1 N9 C8 O17 -175.7(3) . . . . ?
C1 N9 C8 C7 2.7(3) . . . . ?
C1 C6 C5 C4 -0.8(4) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C12 S13 C10 N14 173.5(3) . . . . ?
C12 S13 C10 C7 -7.59(18) . . . . ?
C11 C7 C6 C1 123.1(2) . . . . ?
C11 C7 C6 C5 -58.3(4) . . . . ?
C11 C7 C8 O17 50.1(3) . . . . ?
C11 C7 C8 N9 -128.3(2) . . . . ?
C11 C7 C10 S13 27.7(2) . . . . ?
C11 C7 C10 N14 -153.3(3) . . . . ?
C11 C12 C15 C16 120.5(4) . . . . ?
C5 C6 C1 N9 -179.4(2) . . . . ?
C5 C6 C1 C2 0.5(4) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C15 C12 C11 C7 152.1(2) . . . . ?
C18 N9 C8 O17 0.0(4) . . . . ?
C18 N9 C8 C7 178.4(2) . . . . ?
C18 N9 C1 C6 -176.9(3) . . . . ?
C18 N9 C1 C2 3.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.640
####################################################################### 
# 
# 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_wht-20230921_auto
_database_code_depnum_ccdc_archive 'CCDC 2345928'
_audit_update_record             
;
2024-04-05 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-09-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N O5 S'
_chemical_formula_sum            'C21 H21 N O5 S'
_chemical_formula_weight         399.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1889(3)
_cell_length_b                   23.2839(10)
_cell_length_c                   14.2647(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.583(4)
_cell_angle_gamma                90
_cell_volume                     2354.39(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1400
_cell_measurement_theta_min      6.2320
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.669
_exptl_absorpt_coefficient_mu    1.455
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10565
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.507
_diffrn_reflns_theta_min         3.671
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  21.00   1.00    1.00    --  -35.37  -8.00 -45.00  126
  2  ω      1.00  26.00   1.00    1.00    --  -35.37   8.00 129.00   25
  3  ω      7.00  32.00   1.00    1.00    --   35.37  -8.00 -45.00   25
  4  ω     50.00 103.00   1.00    1.00    --   35.37   8.00 129.00   53
  5  ω    114.00 176.00   1.00    2.12    --  106.81   8.00 129.00   62
  6  ω     38.00  98.00   1.00    2.12    --  106.81  -8.00 -45.00   60
  7  ω    -19.00  22.00   1.00    1.00    --  -35.37  57.00 -30.00   41
  8  ω     61.00 105.00   1.00    1.00    --   35.37 178.00 -90.00   44
  9  ω    -14.00  44.00   1.00    1.00    --   35.37 -77.00 -60.00   58
 10  ω     64.00  89.00   1.00    1.00    --   35.37-178.00   0.00   25
 11  ω      7.00  70.00   1.00    1.00    --   35.37 -99.00-120.00   63
 12  ω     37.00  78.00   1.00    2.12    --  106.81 -30.00  90.00   41
 13  ω     60.00  86.00   1.00    2.12    --  106.81-111.00 150.00   26
 14  ω    106.00 174.00   1.00    2.12    --  106.81  77.00 150.00   68
 15  ω    103.00 173.00   1.00    2.12    --  106.81  77.00  60.00   70
 16  ω     83.00 109.00   1.00    2.12    --  106.81 -30.00  90.00   26
 17  ω     73.00 106.00   1.00    2.12    --  106.81-111.00-120.00   33
 18  ω     42.00  99.00   1.00    2.12    --  106.81-111.00 -30.00   57
 19  ω     41.00  87.00   1.00    2.12    --  106.81 -61.00  30.00   46
 20  ω    123.00 164.00   1.00    2.12    --  106.81 111.00-180.00   41
 21  ω     50.00  99.00   1.00    2.12    --  106.81 -95.00   0.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1449554000
_diffrn_orient_matrix_UB_12      -0.0051848000
_diffrn_orient_matrix_UB_13      0.0678602000
_diffrn_orient_matrix_UB_21      0.1619086000
_diffrn_orient_matrix_UB_22      -0.0043892000
_diffrn_orient_matrix_UB_23      0.0852673000
_diffrn_orient_matrix_UB_31      -0.0007211000
_diffrn_orient_matrix_UB_32      0.0658193000
_diffrn_orient_matrix_UB_33      0.0109508000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3970
_reflns_number_total             4466
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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         0.822
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0813
_refine_ls_restrained_S_all      1.059
_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)+(0.1572P)²+0.9461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2307
_refine_ls_wR_factor_ref         0.2381
_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:
 C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00H(H00H), C00J(H00J), C00K(H00K), C00Q(H00Q), C00R(H00R)
2.d Idealised Me refined as rotating group:
 C00P(H00E,H00F,H00G), C00S(H00I,H00L,H00M), C00T(H00N,H00O,H00P), C00U(H00S,
 H00T,H00U)
;
_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
S001 S 0.88690(10) 0.69225(3) 0.71320(5) 0.0418(2) Uani 1 1 d . . . . .
O002 O 1.1018(3) 0.60986(11) 0.66462(17) 0.0530(6) Uani 1 1 d . . . . .
O003 O 0.5330(4) 0.70453(12) 1.02558(15) 0.0590(7) Uani 1 1 d . . . . .
N004 N 0.7822(3) 0.49667(10) 0.57398(16) 0.0359(5) Uani 1 1 d . . . . .
O005 O 0.2880(3) 0.78687(12) 0.97465(16) 0.0557(6) Uani 1 1 d . . . . .
O006 O 0.8377(4) 0.50483(11) 0.73605(16) 0.0625(7) Uani 1 1 d . . . . .
O007 O 0.1899(4) 0.81899(11) 0.79185(17) 0.0572(6) Uani 1 1 d . . . . .
C009 C 0.7272(3) 0.59021(11) 0.52752(17) 0.0308(5) Uani 1 1 d . . . . .
C00A C 0.7404(3) 0.53363(11) 0.49601(18) 0.0308(5) Uani 1 1 d . . . . .
C00B C 0.5389(4) 0.70727(12) 0.76807(17) 0.0332(5) Uani 1 1 d . . . . .
C00C C 0.6320(4) 0.67918(12) 0.69166(17) 0.0341(6) Uani 1 1 d . . . . .
H00C H 0.578085 0.695682 0.629896 0.041 Uiso 1 1 calc R U . . .
C00D C 0.4059(4) 0.74944(12) 0.74085(18) 0.0352(6) Uani 1 1 d . . . . .
H00D H 0.374463 0.760136 0.677371 0.042 Uiso 1 1 calc R U . . .
C00E C 0.8009(4) 0.52567(12) 0.6577(2) 0.0389(6) Uani 1 1 d . . . . .
C00F C 0.3191(4) 0.77579(12) 0.8104(2) 0.0371(6) Uani 1 1 d . . . . .
C00G C 0.4959(4) 0.71655(13) 0.93098(18) 0.0383(6) Uani 1 1 d . . . . .
C00H C 0.6944(4) 0.63430(13) 0.4631(2) 0.0383(6) Uani 1 1 d . . . . .
H00H H 0.688002 0.672055 0.483663 0.046 Uiso 1 1 calc R U . . .
C00I C 0.9435(4) 0.62501(12) 0.66923(18) 0.0345(6) Uani 1 1 d . . . . .
C00J C 0.5867(4) 0.69079(13) 0.86230(19) 0.0396(6) Uani 1 1 d . . . . .
H00J H 0.678377 0.662853 0.879775 0.048 Uiso 1 1 calc R U . . .
C00K C 0.7175(4) 0.52053(14) 0.4006(2) 0.0433(7) Uani 1 1 d . . . . .
H00K H 0.724946 0.482866 0.379843 0.052 Uiso 1 1 calc R U . . .
C00L C 0.3628(4) 0.75930(13) 0.90429(19) 0.0377(6) Uani 1 1 d . . . . .
C00M C 0.7642(4) 0.58980(11) 0.63472(18) 0.0326(5) Uani 1 1 d . . . . .
C00N C 0.6109(4) 0.61430(13) 0.68593(19) 0.0387(6) Uani 1 1 d . . . . .
H00A H 0.487223 0.604306 0.651438 0.046 Uiso 1 1 calc R U . . .
H00B H 0.623192 0.598223 0.749397 0.046 Uiso 1 1 calc R U . . .
C00P C 0.7975(4) 0.43459(13) 0.5669(2) 0.0460(7) Uani 1 1 d . . . . .
H00E H 0.673586 0.417971 0.555497 0.069 Uiso 1 1 calc R U . . .
H00F H 0.866683 0.419688 0.625197 0.069 Uiso 1 1 calc R U . . .
H00G H 0.862394 0.425131 0.515319 0.069 Uiso 1 1 calc R U . . .
C00Q C 0.6707(5) 0.62157(16) 0.3667(2) 0.0510(8) Uani 1 1 d . . . . .
H00Q H 0.646697 0.650973 0.322229 0.061 Uiso 1 1 calc R U . . .
C00R C 0.6827(5) 0.56577(17) 0.3366(2) 0.0521(8) Uani 1 1 d . . . . .
H00R H 0.667046 0.558146 0.271787 0.062 Uiso 1 1 calc R U . . .
C00S C 0.1660(7) 0.8455(2) 0.7025(3) 0.0757(13) Uani 1 1 d . . . . .
H00I H 0.102495 0.819639 0.655328 0.114 Uiso 1 1 calc R U . . .
H00L H 0.287098 0.855330 0.687199 0.114 Uiso 1 1 calc R U . . .
H00M H 0.091910 0.879722 0.703754 0.114 Uiso 1 1 calc R U . . .
C00T C 0.0986(6) 0.7738(2) 0.9778(3) 0.0727(12) Uani 1 1 d . . . . .
H00N H 0.024849 0.778942 0.915828 0.109 Uiso 1 1 calc R U . . .
H00O H 0.052456 0.798864 1.022222 0.109 Uiso 1 1 calc R U . . .
H00P H 0.088972 0.734660 0.997614 0.109 Uiso 1 1 calc R U . . .
C00U C 0.6617(7) 0.6604(2) 1.0565(3) 0.0828(15) Uani 1 1 d . . . . .
H00S H 0.616643 0.624971 1.026529 0.124 Uiso 1 1 calc R U . . .
H00T H 0.674097 0.656396 1.124255 0.124 Uiso 1 1 calc R U . . .
H00U H 0.782201 0.669610 1.039908 0.124 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
S001 C00C 1.832(3) . ?
S001 C00I 1.759(3) . ?
O002 C00I 1.204(3) . ?
O003 C00G 1.360(3) . ?
O003 C00U 1.404(5) . ?
N004 C00A 1.399(4) . ?
N004 C00E 1.359(4) . ?
N004 C00P 1.455(4) . ?
O005 C00L 1.374(3) . ?
O005 C00T 1.403(5) . ?
O006 C00E 1.207(4) . ?
O007 C00F 1.365(4) . ?
O007 C00S 1.401(5) . ?
C009 C00A 1.400(4) . ?
C009 C00H 1.372(4) . ?
C009 C00M 1.508(3) . ?
C00A C00K 1.378(4) . ?
C00B C00C 1.519(3) . ?
C00B C00D 1.381(4) . ?
C00B C00J 1.385(4) . ?
C00C H00C 0.9800 . ?
C00C C00N 1.519(4) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.398(4) . ?
C00E C00M 1.542(4) . ?
C00F C00L 1.378(4) . ?
C00G C00J 1.399(4) . ?
C00G C00L 1.390(4) . ?
C00H H00H 0.9300 . ?
C00H C00Q 1.390(4) . ?
C00I C00M 1.538(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00R 1.389(5) . ?
C00M C00N 1.530(3) . ?
C00N H00A 0.9700 . ?
C00N H00B 0.9700 . ?
C00P H00E 0.9600 . ?
C00P H00F 0.9600 . ?
C00P H00G 0.9600 . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.375(5) . ?
C00R H00R 0.9300 . ?
C00S H00I 0.9600 . ?
C00S H00L 0.9600 . ?
C00S H00M 0.9600 . ?
C00T H00N 0.9600 . ?
C00T H00O 0.9600 . ?
C00T H00P 0.9600 . ?
C00U H00S 0.9600 . ?
C00U H00T 0.9600 . ?
C00U H00U 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00I S001 C00C 94.39(12) . . ?
C00G O003 C00U 118.2(3) . . ?
C00A N004 C00P 124.4(2) . . ?
C00E N004 C00A 111.7(2) . . ?
C00E N004 C00P 123.9(2) . . ?
C00L O005 C00T 115.0(3) . . ?
C00F O007 C00S 118.5(3) . . ?
C00A C009 C00M 108.0(2) . . ?
C00H C009 C00A 120.2(2) . . ?
C00H C009 C00M 131.7(2) . . ?
N004 C00A C009 109.9(2) . . ?
C00K C00A N004 128.6(2) . . ?
C00K C00A C009 121.5(3) . . ?
C00D C00B C00C 118.2(2) . . ?
C00D C00B C00J 121.2(2) . . ?
C00J C00B C00C 120.6(2) . . ?
S001 C00C H00C 108.7 . . ?
C00B C00C S001 110.85(17) . . ?
C00B C00C H00C 108.7 . . ?
C00B C00C C00N 114.5(2) . . ?
C00N C00C S001 105.22(18) . . ?
C00N C00C H00C 108.7 . . ?
C00B C00D H00D 120.6 . . ?
C00B C00D C00F 118.8(2) . . ?
C00F C00D H00D 120.6 . . ?
N004 C00E C00M 107.8(2) . . ?
O006 C00E N004 126.1(3) . . ?
O006 C00E C00M 126.1(3) . . ?
O007 C00F C00D 123.7(3) . . ?
O007 C00F C00L 115.6(2) . . ?
C00L C00F C00D 120.7(3) . . ?
O003 C00G C00J 124.7(3) . . ?
O003 C00G C00L 115.5(2) . . ?
C00L C00G C00J 119.7(3) . . ?
C009 C00H H00H 120.6 . . ?
C009 C00H C00Q 118.8(3) . . ?
C00Q C00H H00H 120.6 . . ?
O002 C00I S001 123.9(2) . . ?
O002 C00I C00M 125.2(3) . . ?
C00M C00I S001 110.93(18) . . ?
C00B C00J C00G 119.4(3) . . ?
C00B C00J H00J 120.3 . . ?
C00G C00J H00J 120.3 . . ?
C00A C00K H00K 121.3 . . ?
C00A C00K C00R 117.4(3) . . ?
C00R C00K H00K 121.3 . . ?
O005 C00L C00F 121.7(3) . . ?
O005 C00L C00G 118.0(3) . . ?
C00F C00L C00G 120.1(2) . . ?
C009 C00M C00E 102.5(2) . . ?
C009 C00M C00I 108.6(2) . . ?
C009 C00M C00N 117.5(2) . . ?
C00I C00M C00E 110.1(2) . . ?
C00N C00M C00E 111.8(2) . . ?
C00N C00M C00I 106.3(2) . . ?
C00C C00N C00M 108.8(2) . . ?
C00C C00N H00A 109.9 . . ?
C00C C00N H00B 109.9 . . ?
C00M C00N H00A 109.9 . . ?
C00M C00N H00B 109.9 . . ?
H00A C00N H00B 108.3 . . ?
N004 C00P H00E 109.5 . . ?
N004 C00P H00F 109.5 . . ?
N004 C00P H00G 109.5 . . ?
H00E C00P H00F 109.5 . . ?
H00E C00P H00G 109.5 . . ?
H00F C00P H00G 109.5 . . ?
C00H C00Q H00Q 119.8 . . ?
C00R C00Q C00H 120.5(3) . . ?
C00R C00Q H00Q 119.8 . . ?
C00K C00R H00R 119.2 . . ?
C00Q C00R C00K 121.7(3) . . ?
C00Q C00R H00R 119.2 . . ?
O007 C00S H00I 109.5 . . ?
O007 C00S H00L 109.5 . . ?
O007 C00S H00M 109.5 . . ?
H00I C00S H00L 109.5 . . ?
H00I C00S H00M 109.5 . . ?
H00L C00S H00M 109.5 . . ?
O005 C00T H00N 109.5 . . ?
O005 C00T H00O 109.5 . . ?
O005 C00T H00P 109.5 . . ?
H00N C00T H00O 109.5 . . ?
H00N C00T H00P 109.5 . . ?
H00O C00T H00P 109.5 . . ?
O003 C00U H00S 109.5 . . ?
O003 C00U H00T 109.5 . . ?
O003 C00U H00U 109.5 . . ?
H00S C00U H00T 109.5 . . ?
H00S C00U H00U 109.5 . . ?
H00T C00U H00U 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
S001 C00C C00N C00M -37.7(2) . . . . ?
S001 C00I C00M C009 105.1(2) . . . . ?
S001 C00I C00M C00E -143.46(18) . . . . ?
S001 C00I C00M C00N -22.3(3) . . . . ?
O002 C00I C00M C009 -72.9(3) . . . . ?
O002 C00I C00M C00E 38.6(4) . . . . ?
O002 C00I C00M C00N 159.8(3) . . . . ?
O003 C00G C00J C00B -179.0(3) . . . . ?
O003 C00G C00L O005 2.8(4) . . . . ?
O003 C00G C00L C00F 178.2(3) . . . . ?
N004 C00A C00K C00R -177.8(3) . . . . ?
N004 C00E C00M C009 -1.0(3) . . . . ?
N004 C00E C00M C00I -116.3(2) . . . . ?
N004 C00E C00M C00N 125.8(2) . . . . ?
O006 C00E C00M C009 179.8(3) . . . . ?
O006 C00E C00M C00I 64.5(4) . . . . ?
O006 C00E C00M C00N -53.4(4) . . . . ?
O007 C00F C00L O005 -3.3(4) . . . . ?
O007 C00F C00L C00G -178.6(3) . . . . ?
C009 C00A C00K C00R 0.7(4) . . . . ?
C009 C00H C00Q C00R -0.8(5) . . . . ?
C009 C00M C00N C00C -83.0(3) . . . . ?
C00A N004 C00E O006 -179.6(3) . . . . ?
C00A N004 C00E C00M 1.2(3) . . . . ?
C00A C009 C00H C00Q 1.3(4) . . . . ?
C00A C009 C00M C00E 0.4(3) . . . . ?
C00A C009 C00M C00I 116.9(2) . . . . ?
C00A C009 C00M C00N -122.5(2) . . . . ?
C00A C00K C00R C00Q -0.2(5) . . . . ?
C00B C00C C00N C00M -159.7(2) . . . . ?
C00B C00D C00F O007 178.1(3) . . . . ?
C00B C00D C00F C00L -1.2(4) . . . . ?
C00C S001 C00I O002 178.6(3) . . . . ?
C00C S001 C00I C00M 0.7(2) . . . . ?
C00C C00B C00D C00F -179.9(2) . . . . ?
C00C C00B C00J C00G -178.7(3) . . . . ?
C00D C00B C00C S001 118.1(2) . . . . ?
C00D C00B C00C C00N -123.1(3) . . . . ?
C00D C00B C00J C00G 1.3(4) . . . . ?
C00D C00F C00L O005 176.0(3) . . . . ?
C00D C00F C00L C00G 0.8(4) . . . . ?
C00E N004 C00A C009 -0.9(3) . . . . ?
C00E N004 C00A C00K 177.7(3) . . . . ?
C00E C00M C00N C00C 158.9(2) . . . . ?
C00H C009 C00A N004 177.5(2) . . . . ?
C00H C009 C00A C00K -1.3(4) . . . . ?
C00H C009 C00M C00E -176.4(3) . . . . ?
C00H C009 C00M C00I -59.9(3) . . . . ?
C00H C009 C00M C00N 60.7(4) . . . . ?
C00H C00Q C00R C00K 0.3(5) . . . . ?
C00I S001 C00C C00B 145.5(2) . . . . ?
C00I S001 C00C C00N 21.16(18) . . . . ?
C00I C00M C00N C00C 38.7(3) . . . . ?
C00J C00B C00C S001 -62.0(3) . . . . ?
C00J C00B C00C C00N 56.9(3) . . . . ?
C00J C00B C00D C00F 0.2(4) . . . . ?
C00J C00G C00L O005 -174.7(3) . . . . ?
C00J C00G C00L C00F 0.7(4) . . . . ?
C00L C00G C00J C00B -1.7(4) . . . . ?
C00M C009 C00A N004 0.2(3) . . . . ?
C00M C009 C00A C00K -178.5(2) . . . . ?
C00M C009 C00H C00Q 177.8(3) . . . . ?
C00P N004 C00A C009 177.2(2) . . . . ?
C00P N004 C00A C00K -4.2(4) . . . . ?
C00P N004 C00E O006 2.3(5) . . . . ?
C00P N004 C00E C00M -176.9(2) . . . . ?
C00S O007 C00F C00D -11.6(5) . . . . ?
C00S O007 C00F C00L 167.7(3) . . . . ?
C00T O005 C00L C00F 75.3(4) . . . . ?
C00T O005 C00L C00G -109.4(4) . . . . ?
C00U O003 C00G C00J -4.7(5) . . . . ?
C00U O003 C00G C00L 177.9(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.036 0.000 0.500 271.4 100.1 ?
2 -0.198 0.500 0.000 271.4 100.1 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 2.569
_oxdiff_exptl_absorpt_empirical_full_min 0.572
####################################################################### 
# 
# 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_wht-20231008_auto
_database_code_depnum_ccdc_archive 'CCDC 2345331'
_audit_update_record             
;
2024-04-02 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-10-08
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N O3 S'
_chemical_formula_sum            'C15 H13 Cl N O3 S0.50'
_chemical_formula_weight         306.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.0117(5)
_cell_length_b                   9.0391(5)
_cell_length_c                   11.6902(6)
_cell_angle_alpha                88.875(5)
_cell_angle_beta                 79.609(5)
_cell_angle_gamma                74.816(5)
_cell_volume                     703.03(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3292
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2660
_cell_measurement_theta_min      6.2770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             318
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4840
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         83.539
_diffrn_reflns_theta_min         3.846
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 -44.00   1.00    1.00    --  -35.37 123.00  74.00   25
  2  ω    -60.00 -21.00   1.00    1.00    --  -35.37 149.00-122.00   39
  3  ω     47.00  80.00   1.00    1.00    --   35.37-123.00  -5.00   33
  4  ω    135.00 171.00   1.00    1.00    --  106.81 123.00  74.00   36
  5  ω     85.00 110.00   1.00    1.00    --  106.81-123.00  -5.00   25
  6  ω    101.00 126.00   1.00    1.00    --  106.81 149.00-122.00   25
  7  ω     70.00 129.00   1.00    1.00    --  106.81-149.00-169.00   59
  8  ω     40.00  66.00   1.00    1.00    --  106.81-149.00-169.00   26
  9  ω   -103.00 -26.00   1.00    1.00    --  -35.37 -38.00-120.00   77
 10  ω   -106.00 -24.00   1.00    1.00    --  -35.37 -19.00 150.00   82
 11  ω     77.00 102.00   1.00    1.00    --   35.37-149.00-169.00   25
 12  ω     55.00 105.00   1.00    1.00    --   35.37  19.00-120.00   50
 13  ω      7.00  39.00   1.00    1.00    --   35.37  19.00-120.00   32
 14  ω     76.00 106.00   1.00    1.00    --   35.37 178.00 -60.00   30
 15  ω    -32.00  51.00   1.00    1.00    --   35.37 -38.00  60.00   83
 16  ω     64.00 107.00   1.00    1.00    --   35.37 178.00 120.00   43
 17  ω     90.00 174.00   1.00    1.00    --  106.81  45.00 150.00   84
 18  ω     43.00  69.00   1.00    1.00    --  106.81-111.00 -60.00   26
 19  ω     75.00 108.00   1.00    1.00    --  106.81 -30.00-180.00   33
 20  ω     86.00 175.00   1.00    1.00    --  106.81  30.00  60.00   89
 21  ω     40.00  67.00   1.00    1.00    --  106.81 -30.00-180.00   27
 22  ω     56.00  82.00   1.00    1.00    --  106.81-111.00-120.00   26
 23  ω     90.00 172.00   1.00    1.00    --  106.81  61.00  90.00   82
 24  ω     40.00 133.00   1.00    1.00    --  106.81 -77.00 150.00   93
 25  ω     41.00 125.00   1.00    1.00    --  106.81 -30.00  90.00   84
 26  ω     77.00 107.00   1.00    1.00    --  106.81-111.00  30.00   30
 27  ω     64.00 104.00   1.00    1.00    --  106.81 -61.00  30.00   40
 28  ω     49.00  76.00   1.00    1.00    --  106.81-111.00  30.00   27
 29  ω     83.00 108.00   1.00    1.00    --  106.81-111.00-120.00   25
 30  ω     63.00 120.00   1.00    1.00    --  106.81 -45.00   0.00   57
 31  ω     43.00 125.00   1.00    1.00    --  106.81 -61.00 -60.00   82
 32  ω    123.00 148.00   1.00    1.00    --  106.81  77.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0175107000
_diffrn_orient_matrix_UB_12      -0.0857863000
_diffrn_orient_matrix_UB_13      0.1150077000
_diffrn_orient_matrix_UB_21      -0.0949605000
_diffrn_orient_matrix_UB_22      0.1540338000
_diffrn_orient_matrix_UB_23      0.0675471000
_diffrn_orient_matrix_UB_31      -0.2104092000
_diffrn_orient_matrix_UB_32      -0.0113062000
_diffrn_orient_matrix_UB_33      -0.0132754000
_diffrn_oxdiff_digest_frames     
;
0105069e82df0d901b9fcfea654aab9fde00027185c
;
_diffrn_oxdiff_digest_hkl        
;
0121df8f21e9781eba76e6121544c05aff7383
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2290
_reflns_number_total             2654
_reflns_odcompleteness_completeness 98.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.339
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1336P)²+0.8921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2177
_refine_ls_wR_factor_ref         0.2360
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C15(H15), C7(H7)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_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
S13 S 0.39838(13) 0.74619(11) 0.54585(8) 0.0453(3) Uani 1 1 d . . . . .
O14 O 0.6152(4) 0.6255(3) 0.7020(2) 0.0504(7) Uani 1 1 d . . . . .
O19 O 0.1004(5) 0.8824(3) 0.8178(3) 0.0642(9) Uani 1 1 d . . . . .
O17 O 0.5256(5) 0.0678(3) 0.8551(3) 0.0607(8) Uani 1 1 d . . . . .
N9 N 0.1719(5) 0.6855(4) 0.9447(3) 0.0443(7) Uani 1 1 d . . . . .
C10 C 0.4534(5) 0.6543(4) 0.6737(3) 0.0344(7) Uani 1 1 d . . . . .
C2 C 0.2653(5) 0.6163(4) 0.7454(3) 0.0342(7) Uani 1 1 d . . . . .
C11 C 0.1277(5) 0.6109(4) 0.6586(3) 0.0377(7) Uani 1 1 d . . . . .
H11A H 0.171379 0.512344 0.617383 0.045 Uiso 1 1 calc R . . . .
H11B H -0.009051 0.623766 0.699677 0.045 Uiso 1 1 calc R . . . .
C12 C 0.1353(5) 0.7396(4) 0.5719(3) 0.0378(7) Uani 1 1 d . . . . .
H12 H 0.050351 0.836953 0.608517 0.045 Uiso 1 1 calc R . . . .
C3 C 0.3136(5) 0.4798(4) 0.8192(3) 0.0349(7) Uani 1 1 d . . . . .
C8 C 0.2570(5) 0.5259(4) 0.9355(3) 0.0397(8) Uani 1 1 d . . . . .
C4 C 0.4049(5) 0.3269(4) 0.7872(3) 0.0382(8) Uani 1 1 d . . . . .
H4 H 0.444108 0.295743 0.709233 0.046 Uiso 1 1 calc R . . . .
C5 C 0.4361(5) 0.2217(4) 0.8746(3) 0.0443(9) Uani 1 1 d . . . . .
C1 C 0.1677(5) 0.7483(4) 0.8386(3) 0.0422(8) Uani 1 1 d . . . . .
C6 C 0.3780(6) 0.2698(5) 0.9910(3) 0.0521(10) Uani 1 1 d . . . . .
H6 H 0.400754 0.197957 1.048425 0.063 Uiso 1 1 calc R . . . .
C15 C 0.0720(6) 0.7141(5) 0.4606(3) 0.0488(9) Uani 1 1 d . . . . .
H15 H 0.138999 0.623811 0.418104 0.059 Uiso 1 1 calc R . . . .
C7 C 0.2873(6) 0.4215(5) 1.0233(3) 0.0498(10) Uani 1 1 d . . . . .
H7 H 0.247861 0.452664 1.101259 0.060 Uiso 1 1 calc R . . . .
C16 C -0.0717(8) 0.8102(6) 0.4186(5) 0.0704(14) Uani 1 1 d . . . . .
C18 C 0.5974(9) 0.0143(5) 0.7392(5) 0.0707(13) Uani 1 1 d . . . . .
H18A H 0.487875 0.035262 0.697333 0.106 Uiso 1 1 calc GR . . . .
H18B H 0.657363 -0.094267 0.737703 0.106 Uiso 1 1 calc GR . . . .
H18C H 0.696169 0.065270 0.703439 0.106 Uiso 1 1 calc GR . . . .
C20 C 0.0921(7) 0.7729(6) 1.0537(4) 0.0625(12) Uani 1 1 d . . . . .
H20A H -0.008350 0.730853 1.099264 0.094 Uiso 1 1 calc GR . . . .
H20B H 0.033053 0.877942 1.037806 0.094 Uiso 1 1 calc GR . . . .
H20C H 0.198831 0.767839 1.096025 0.094 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S13 C10 1.751(3) . ?
S13 C12 1.831(3) . ?
O14 C10 1.201(4) . ?
O19 C1 1.217(5) . ?
O17 C5 1.372(5) . ?
O17 C18 1.405(6) . ?
N9 C8 1.407(5) . ?
N9 C1 1.356(5) . ?
N9 C20 1.453(5) . ?
C10 C2 1.545(5) . ?
C2 C11 1.531(4) . ?
C2 C3 1.493(4) . ?
C2 C1 1.560(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.533(5) . ?
C12 H12 0.9800 . ?
C12 C15 1.489(5) . ?
C3 C8 1.385(5) . ?
C3 C4 1.389(5) . ?
C8 C7 1.388(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(5) . ?
C5 C6 1.392(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.310(6) . ?
C7 H7 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S13 C12 95.26(15) . . ?
C5 O17 C18 117.8(3) . . ?
C8 N9 C20 124.8(3) . . ?
C1 N9 C8 111.6(3) . . ?
C1 N9 C20 123.6(4) . . ?
O14 C10 S13 124.5(3) . . ?
O14 C10 C2 124.7(3) . . ?
C2 C10 S13 110.8(2) . . ?
C10 C2 C1 107.0(3) . . ?
C11 C2 C10 105.8(3) . . ?
C11 C2 C1 111.8(3) . . ?
C3 C2 C10 113.4(3) . . ?
C3 C2 C11 116.6(3) . . ?
C3 C2 C1 102.0(3) . . ?
C2 C11 H11A 109.8 . . ?
C2 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 C2 109.2(3) . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.8 . . ?
S13 C12 H12 109.2 . . ?
C11 C12 S13 104.3(2) . . ?
C11 C12 H12 109.2 . . ?
C15 C12 S13 110.7(3) . . ?
C15 C12 C11 114.1(3) . . ?
C15 C12 H12 109.2 . . ?
C8 C3 C2 109.3(3) . . ?
C8 C3 C4 120.7(3) . . ?
C4 C3 C2 130.0(3) . . ?
C3 C8 N9 109.7(3) . . ?
C3 C8 C7 121.3(4) . . ?
C7 C8 N9 129.0(3) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.3(3) . . ?
C5 C4 H4 120.8 . . ?
O17 C5 C4 124.3(4) . . ?
O17 C5 C6 115.4(3) . . ?
C4 C5 C6 120.3(4) . . ?
O19 C1 N9 127.3(3) . . ?
O19 C1 C2 125.3(3) . . ?
N9 C1 C2 107.4(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(4) . . ?
C7 C6 H6 119.2 . . ?
C12 C15 H15 117.8 . . ?
C16 C15 C12 124.4(4) . . ?
C16 C15 H15 117.8 . . ?
C8 C7 H7 121.1 . . ?
C6 C7 C8 117.7(3) . . ?
C6 C7 H7 121.1 . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
O17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N9 C20 H20A 109.5 . . ?
N9 C20 H20B 109.5 . . ?
N9 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
S13 C10 C2 C11 23.0(3) . . . . ?
S13 C10 C2 C3 152.1(2) . . . . ?
S13 C10 C2 C1 -96.3(3) . . . . ?
S13 C12 C15 C16 -118.7(5) . . . . ?
O14 C10 C2 C11 -157.4(3) . . . . ?
O14 C10 C2 C3 -28.3(5) . . . . ?
O14 C10 C2 C1 83.3(4) . . . . ?
O17 C5 C6 C7 179.6(3) . . . . ?
N9 C8 C7 C6 -178.9(3) . . . . ?
C10 S13 C12 C11 -20.8(2) . . . . ?
C10 S13 C12 C15 -143.9(3) . . . . ?
C10 C2 C11 C12 -39.5(3) . . . . ?
C10 C2 C3 C8 113.7(3) . . . . ?
C10 C2 C3 C4 -64.7(4) . . . . ?
C10 C2 C1 O19 62.3(4) . . . . ?
C10 C2 C1 N9 -118.0(3) . . . . ?
C2 C11 C12 S13 37.9(3) . . . . ?
C2 C11 C12 C15 158.8(3) . . . . ?
C2 C3 C8 N9 0.4(4) . . . . ?
C2 C3 C8 C7 -179.3(3) . . . . ?
C2 C3 C4 C5 178.8(3) . . . . ?
C11 C2 C3 C8 -123.1(3) . . . . ?
C11 C2 C3 C4 58.6(5) . . . . ?
C11 C2 C1 O19 -53.1(5) . . . . ?
C11 C2 C1 N9 126.6(3) . . . . ?
C11 C12 C15 C16 124.1(5) . . . . ?
C12 S13 C10 O14 179.2(3) . . . . ?
C12 S13 C10 C2 -1.2(2) . . . . ?
C3 C2 C11 C12 -166.6(3) . . . . ?
C3 C2 C1 O19 -178.4(4) . . . . ?
C3 C2 C1 N9 1.3(3) . . . . ?
C3 C8 C7 C6 0.7(5) . . . . ?
C3 C4 C5 O17 -179.5(3) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C8 N9 C1 O19 178.6(4) . . . . ?
C8 N9 C1 C2 -1.2(4) . . . . ?
C8 C3 C4 C5 0.6(5) . . . . ?
C4 C3 C8 N9 178.9(3) . . . . ?
C4 C3 C8 C7 -0.7(5) . . . . ?
C4 C5 C6 C7 0.4(6) . . . . ?
C5 C6 C7 C8 -0.5(6) . . . . ?
C1 N9 C8 C3 0.5(4) . . . . ?
C1 N9 C8 C7 -179.8(3) . . . . ?
C1 C2 C11 C12 76.7(3) . . . . ?
C1 C2 C3 C8 -1.0(3) . . . . ?
C1 C2 C3 C4 -179.4(3) . . . . ?
C18 O17 C5 C4 2.6(6) . . . . ?
C18 O17 C5 C6 -176.5(4) . . . . ?
C20 N9 C8 C3 178.7(3) . . . . ?
C20 N9 C8 C7 -1.7(6) . . . . ?
C20 N9 C1 O19 0.4(6) . . . . ?
C20 N9 C1 C2 -179.4(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 3.096
_oxdiff_exptl_absorpt_empirical_full_min 0.497
