# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_241119wjw
_database_code_depnum_ccdc_archive 'CCDC 2431747'
loop_
_audit_author_name
_audit_author_address
'Liyan Yuwen'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2025-03-16 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_audit_creation_date             2024-11-19
_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         'C19 H20 O S'
_chemical_formula_sum            'C19 H20 O S'
_chemical_formula_weight         296.41
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1143(5)
_cell_length_b                   7.2877(3)
_cell_length_c                   12.1106(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.273(2)
_cell_angle_gamma                90
_cell_volume                     796.04(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4098
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.389
_cell_measurement_theta_min      2.623
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1653 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.7933.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8276
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         2.624
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.772
_reflns_Friedel_fraction_max     0.709
_reflns_number_gt                2632
_reflns_number_total             3156
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.041
_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)+(0.0530P)²+0.0040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1027
_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:
 C1(H1), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18255(8) 0.67403(9) 0.52253(6) 0.0414(2) Uani 1 1 d . . . . .
O1 O 0.0597(3) 0.7031(4) 0.42792(16) 0.0609(7) Uani 1 1 d . . . . .
C1 C 0.0958(3) 0.6047(4) 0.6380(2) 0.0391(6) Uani 1 1 d . . . . .
H1 H 0.039238 0.490081 0.628039 0.047 Uiso 1 1 calc R U . . .
C2 C 0.0296(4) 0.7525(5) 0.7020(3) 0.0514(8) Uani 1 1 d . . . . .
H2A H -0.064839 0.727261 0.727019 0.062 Uiso 1 1 calc R U . . .
H2B H 0.043674 0.878896 0.680766 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1634(3) 0.6484(4) 0.7568(2) 0.0380(7) Uani 1 1 d . . . . .
C4 C 0.3115(4) 0.7444(5) 0.7899(2) 0.0497(8) Uani 1 1 d . . . . .
H4A H 0.304651 0.873371 0.769939 0.060 Uiso 1 1 calc R U . . .
H4B H 0.388369 0.687866 0.753675 0.060 Uiso 1 1 calc R U . . .
C5 C 0.3441(4) 0.7205(5) 0.9166(3) 0.0624(10) Uani 1 1 d . . . . .
H5A H 0.449270 0.702540 0.940707 0.075 Uiso 1 1 calc R U . . .
H5B H 0.311026 0.826477 0.954723 0.075 Uiso 1 1 calc R U . . .
C6 C 0.2572(3) 0.5516(5) 0.9388(3) 0.0454(7) Uani 1 1 d . . . . .
C7 C 0.2711(4) 0.4391(5) 1.0316(3) 0.0555(9) Uani 1 1 d . . . . .
H7 H 0.341840 0.464220 1.093006 0.067 Uiso 1 1 calc R U . . .
C8 C 0.1795(4) 0.2900(6) 1.0322(3) 0.0639(10) Uani 1 1 d . . . . .
H8 H 0.188315 0.214723 1.094764 0.077 Uiso 1 1 calc R U . . .
C9 C 0.0746(4) 0.2498(6) 0.9417(3) 0.0651(10) Uani 1 1 d . . . . .
H9 H 0.014043 0.147447 0.943402 0.078 Uiso 1 1 calc R U . . .
C10 C 0.0592(4) 0.3624(5) 0.8474(3) 0.0523(8) Uani 1 1 d . . . . .
H10 H -0.011892 0.336644 0.786239 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1510(3) 0.5121(4) 0.8464(2) 0.0385(7) Uani 1 1 d . . . . .
C12 C 0.2660(3) 0.4508(4) 0.4940(2) 0.0379(6) Uani 1 1 d . . . . .
H12 H 0.188883 0.356269 0.489665 0.046 Uiso 1 1 calc R U . . .
C13 C 0.3177(4) 0.4663(5) 0.3804(2) 0.0489(8) Uani 1 1 d . . . . .
H13A H 0.236507 0.505266 0.326003 0.073 Uiso 1 1 calc R U . . .
H13B H 0.352768 0.349065 0.359185 0.073 Uiso 1 1 calc R U . . .
H13C H 0.396569 0.554496 0.384183 0.073 Uiso 1 1 calc R U . . .
C14 C 0.3849(3) 0.4053(4) 0.5901(2) 0.0359(6) Uani 1 1 d . . . . .
C15 C 0.5268(3) 0.4791(4) 0.5971(3) 0.0467(7) Uani 1 1 d . . . . .
H15 H 0.551291 0.550655 0.538790 0.056 Uiso 1 1 calc R U . . .
C16 C 0.6323(4) 0.4475(5) 0.6898(3) 0.0536(8) Uani 1 1 d . . . . .
H16 H 0.727316 0.495755 0.692895 0.064 Uiso 1 1 calc R U . . .
C17 C 0.5957(4) 0.3446(5) 0.7770(3) 0.0550(9) Uani 1 1 d . . . . .
H17 H 0.665216 0.326657 0.840240 0.066 Uiso 1 1 calc R U . . .
C18 C 0.4569(4) 0.2680(5) 0.7712(3) 0.0507(8) Uani 1 1 d . . . . .
H18 H 0.433194 0.197295 0.830048 0.061 Uiso 1 1 calc R U . . .
C19 C 0.3524(3) 0.2961(4) 0.6777(2) 0.0410(7) Uani 1 1 d . . . . .
H19 H 0.259557 0.241437 0.673497 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4973(19) . ?
S1 C1 1.776(3) . ?
S1 C12 1.850(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.503(4) . ?
C1 C3 1.515(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.506(4) . ?
C3 C4 1.523(4) . ?
C3 C11 1.488(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.530(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.508(5) . ?
C6 C7 1.383(4) . ?
C6 C11 1.400(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.397(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(4) . ?
C12 H12 0.9800 . ?
C12 C13 1.522(4) . ?
C12 C14 1.509(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.392(4) . ?
C14 C19 1.392(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(4) . ?
C19 H19 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
O1 S1 C1 105.93(13) . . ?
O1 S1 C12 105.29(13) . . ?
C1 S1 C12 97.96(14) . . ?
S1 C1 H1 115.5 . . ?
C2 C1 S1 117.4(2) . . ?
C2 C1 H1 115.5 . . ?
C2 C1 C3 59.89(19) . . ?
C3 C1 S1 121.5(2) . . ?
C3 C1 H1 115.5 . . ?
C1 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
C1 C2 C3 60.44(19) . . ?
H2A C2 H2B 114.8 . . ?
C3 C2 H2A 117.7 . . ?
C3 C2 H2B 117.7 . . ?
C1 C3 C4 124.8(2) . . ?
C2 C3 C1 59.67(19) . . ?
C2 C3 C4 121.0(3) . . ?
C11 C3 C1 119.3(2) . . ?
C11 C3 C2 121.1(2) . . ?
C11 C3 C4 105.8(2) . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C3 C4 C5 104.4(3) . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C6 C5 C4 103.9(2) . . ?
C6 C5 H5A 111.0 . . ?
C6 C5 H5B 111.0 . . ?
C7 C6 C5 129.8(3) . . ?
C7 C6 C11 119.9(3) . . ?
C11 C6 C5 110.3(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H10 120.6 . . ?
C6 C11 C3 109.2(3) . . ?
C10 C11 C3 130.2(3) . . ?
C10 C11 C6 120.6(3) . . ?
S1 C12 H12 108.5 . . ?
C13 C12 S1 107.0(2) . . ?
C13 C12 H12 108.5 . . ?
C14 C12 S1 108.55(18) . . ?
C14 C12 H12 108.5 . . ?
C14 C12 C13 115.6(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 121.3(3) . . ?
C15 C14 C19 118.2(3) . . ?
C19 C14 C12 120.4(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.7(3) . . ?
C18 C19 H19 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 -112.3(2) . . . . ?
S1 C1 C3 C2 105.5(3) . . . . ?
S1 C1 C3 C4 -3.2(4) . . . . ?
S1 C1 C3 C11 -143.5(2) . . . . ?
S1 C12 C14 C15 -81.9(3) . . . . ?
S1 C12 C14 C19 94.3(3) . . . . ?
O1 S1 C1 C2 -80.3(3) . . . . ?
O1 S1 C1 C3 -150.0(2) . . . . ?
O1 S1 C12 C13 58.3(2) . . . . ?
O1 S1 C12 C14 -176.30(19) . . . . ?
C1 S1 C12 C13 167.27(19) . . . . ?
C1 S1 C12 C14 -67.3(2) . . . . ?
C1 C2 C3 C4 114.8(3) . . . . ?
C1 C2 C3 C11 -108.0(3) . . . . ?
C1 C3 C4 C5 -168.7(3) . . . . ?
C1 C3 C11 C6 161.4(3) . . . . ?
C1 C3 C11 C10 -16.3(4) . . . . ?
C2 C1 C3 C4 -108.7(3) . . . . ?
C2 C1 C3 C11 110.9(3) . . . . ?
C2 C3 C4 C5 118.7(3) . . . . ?
C2 C3 C11 C6 -128.3(3) . . . . ?
C2 C3 C11 C10 54.0(5) . . . . ?
C3 C4 C5 C6 24.4(3) . . . . ?
C4 C3 C11 C6 14.4(3) . . . . ?
C4 C3 C11 C10 -163.3(3) . . . . ?
C4 C5 C6 C7 162.3(4) . . . . ?
C4 C5 C6 C11 -16.6(4) . . . . ?
C5 C6 C7 C8 -179.2(4) . . . . ?
C5 C6 C11 C3 1.5(3) . . . . ?
C5 C6 C11 C10 179.4(3) . . . . ?
C6 C7 C8 C9 0.4(6) . . . . ?
C7 C6 C11 C3 -177.6(3) . . . . ?
C7 C6 C11 C10 0.4(5) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C3 177.0(3) . . . . ?
C9 C10 C11 C6 -0.5(5) . . . . ?
C11 C3 C4 C5 -24.0(3) . . . . ?
C11 C6 C7 C8 -0.4(5) . . . . ?
C12 S1 C1 C2 171.3(2) . . . . ?
C12 S1 C1 C3 101.5(2) . . . . ?
C12 C14 C15 C16 175.2(3) . . . . ?
C12 C14 C19 C18 -173.8(3) . . . . ?
C13 C12 C14 C15 38.3(4) . . . . ?
C13 C12 C14 C19 -145.5(3) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C15 C14 C19 C18 2.5(4) . . . . ?
C15 C16 C17 C18 2.1(5) . . . . ?
C16 C17 C18 C19 -0.8(5) . . . . ?
C17 C18 C19 C14 -1.6(5) . . . . ?
C19 C14 C15 C16 -1.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_250507yw_frg_2
_database_code_depnum_ccdc_archive 'CCDC 2450395'
loop_
_audit_author_name
_audit_author_address
'Liyan Yuwen'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2025-05-11 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_audit_creation_date             2025-05-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 F O3 S'
_chemical_formula_sum            'C19 H25 F O3 S'
_chemical_formula_weight         352.45
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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                   10.1006(3)
_cell_length_b                   10.2657(4)
_cell_length_c                   17.6580(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1830.95(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.917
_cell_measurement_theta_min      4.335
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    1.184
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.2599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1713 before and 0.1050 after correction.
The Ratio of minimum to maximum transmission is 0.3462.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1303
_diffrn_reflns_av_unetI/netI     0.0983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18154
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.024
_diffrn_reflns_theta_min         4.334
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2491146
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2988
_reflns_number_total             3491
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0714
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1117P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1743
_refine_ls_wR_factor_ref         0.1806
_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:
 C1(H1), C4(H4), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,
 H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32110(13) 0.31735(11) 0.35761(8) 0.0617(4) Uani 1 1 d . . . . .
F1 F 0.1089(5) 0.7564(4) 0.1846(2) 0.1060(14) Uani 1 1 d . . . . .
O1 O 0.4406(4) 0.2636(4) 0.3178(3) 0.0883(13) Uani 1 1 d . . . . .
O2 O 0.3768(2) 0.8764(3) 0.46146(17) 0.0493(7) Uani 1 1 d . . . . .
O3 O 0.1600(3) 0.9169(3) 0.43655(19) 0.0564(8) Uani 1 1 d . . . . .
C1 C 0.3794(4) 0.4199(4) 0.4311(3) 0.0510(10) Uani 1 1 d . . . . .
H1 H 0.443109 0.488128 0.413639 0.061 Uiso 1 1 calc R U . . .
C2 C 0.4044(4) 0.3728(4) 0.5094(3) 0.0565(11) Uani 1 1 d . . . . .
H2A H 0.482407 0.408143 0.536404 0.068 Uiso 1 1 calc R U . . .
H2B H 0.383771 0.280602 0.520806 0.068 Uiso 1 1 calc R U . . .
C3 C 0.2898(4) 0.4638(4) 0.4950(3) 0.0457(9) Uani 1 1 d . . . . .
C4 C 0.3068(4) 0.6073(4) 0.5160(2) 0.0417(8) Uani 1 1 d . . . . .
H4 H 0.401642 0.630650 0.507110 0.050 Uiso 1 1 calc R U . . .
C5 C 0.2761(4) 0.6358(4) 0.5983(3) 0.0502(10) Uani 1 1 d . . . . .
H5A H 0.333117 0.581352 0.631169 0.060 Uiso 1 1 calc R U . . .
H5B H 0.182685 0.613288 0.609081 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2996(4) 0.7797(4) 0.6162(2) 0.0515(10) Uani 1 1 d . . . . .
H6A H 0.395010 0.799455 0.610296 0.062 Uiso 1 1 calc R U . . .
H6B H 0.275377 0.796511 0.669679 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2192(4) 0.8708(4) 0.5648(3) 0.0512(10) Uani 1 1 d . . . . .
H7 H 0.123305 0.853972 0.574828 0.061 Uiso 1 1 calc R U . . .
C8 C 0.2454(4) 0.8384(4) 0.4826(3) 0.0451(10) Uani 1 1 d . . . . .
C9 C 0.2221(3) 0.6949(4) 0.4649(2) 0.0420(8) Uani 1 1 d . . . . .
H9A H 0.244503 0.677898 0.411186 0.050 Uiso 1 1 calc R U . . .
H9B H 0.127362 0.673883 0.472315 0.050 Uiso 1 1 calc R U . . .
C10 C 0.2469(5) 1.0134(5) 0.5843(3) 0.0660(13) Uani 1 1 d . . . . .
H10A H 0.341244 1.031844 0.577153 0.099 Uiso 1 1 calc R U . . .
H10B H 0.222591 1.029756 0.637201 0.099 Uiso 1 1 calc R U . . .
H10C H 0.194506 1.069951 0.551122 0.099 Uiso 1 1 calc R U . . .
C11 C 0.1521(4) 0.4065(4) 0.5037(3) 0.0539(10) Uani 1 1 d . . . . .
H11A H 0.126699 0.407632 0.557229 0.081 Uiso 1 1 calc R U . . .
H11B H 0.151930 0.316500 0.485129 0.081 Uiso 1 1 calc R U . . .
H11C H 0.088875 0.458294 0.474295 0.081 Uiso 1 1 calc R U . . .
C12 C 0.3722(5) 0.9202(6) 0.3865(3) 0.0719(14) Uani 1 1 d . . . . .
H12A H 0.409035 0.853587 0.351845 0.086 Uiso 1 1 calc R U . . .
H12B H 0.424013 1.001454 0.380729 0.086 Uiso 1 1 calc R U . . .
C13 C 0.2288(5) 0.9444(5) 0.3689(3) 0.0661(13) Uani 1 1 d . . . . .
H13A H 0.214729 1.036092 0.353514 0.079 Uiso 1 1 calc R U . . .
H13B H 0.198403 0.886678 0.327512 0.079 Uiso 1 1 calc R U . . .
C14 C 0.2572(4) 0.4482(4) 0.3012(2) 0.0489(10) Uani 1 1 d . . . . .
C15 C 0.1234(4) 0.4676(5) 0.2983(3) 0.0580(11) Uani 1 1 d . . . . .
H15 H 0.065468 0.409011 0.323484 0.070 Uiso 1 1 calc R U . . .
C16 C 0.0724(5) 0.5718(6) 0.2588(3) 0.0669(14) Uani 1 1 d . . . . .
H16 H -0.020375 0.586121 0.255990 0.080 Uiso 1 1 calc R U . . .
C17 C 0.1597(6) 0.6539(5) 0.2239(3) 0.0669(13) Uani 1 1 d . . . . .
C18 C 0.2939(5) 0.6381(5) 0.2245(3) 0.0629(12) Uani 1 1 d . . . . .
H18 H 0.350804 0.697455 0.199148 0.075 Uiso 1 1 calc R U . . .
C19 C 0.3434(4) 0.5321(5) 0.2636(3) 0.0547(11) Uani 1 1 d . . . . .
H19 H 0.436122 0.516489 0.264874 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.502(4) . ?
S1 C1 1.771(4) . ?
S1 C14 1.792(5) . ?
F1 C17 1.361(6) . ?
O2 C8 1.433(5) . ?
O2 C12 1.399(6) . ?
O3 C8 1.434(5) . ?
O3 C13 1.411(6) . ?
C1 H1 1.0000 . ?
C1 C2 1.486(7) . ?
C1 C3 1.515(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.509(5) . ?
C3 C4 1.529(5) . ?
C3 C11 1.518(5) . ?
C4 H4 1.0000 . ?
C4 C5 1.515(6) . ?
C4 C9 1.535(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.529(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.536(6) . ?
C7 H7 1.0000 . ?
C7 C8 1.511(6) . ?
C7 C10 1.530(7) . ?
C8 C9 1.524(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.501(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.367(6) . ?
C14 C19 1.393(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.367(8) . ?
C17 C18 1.365(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(7) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C1 107.1(2) . . ?
O1 S1 C14 107.7(2) . . ?
C1 S1 C14 94.7(2) . . ?
C12 O2 C8 107.7(3) . . ?
C13 O3 C8 107.2(3) . . ?
S1 C1 H1 113.9 . . ?
C2 C1 S1 123.0(3) . . ?
C2 C1 H1 113.9 . . ?
C2 C1 C3 60.4(3) . . ?
C3 C1 S1 121.6(3) . . ?
C3 C1 H1 113.9 . . ?
C1 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
C1 C2 C3 60.8(3) . . ?
H2A C2 H2B 114.8 . . ?
C3 C2 H2A 117.7 . . ?
C3 C2 H2B 117.7 . . ?
C1 C3 C4 113.6(3) . . ?
C1 C3 C11 120.5(4) . . ?
C2 C3 C1 58.9(3) . . ?
C2 C3 C4 118.0(3) . . ?
C2 C3 C11 116.5(3) . . ?
C11 C3 C4 116.8(3) . . ?
C3 C4 H4 107.5 . . ?
C3 C4 C9 111.1(3) . . ?
C5 C4 C3 113.4(3) . . ?
C5 C4 H4 107.5 . . ?
C5 C4 C9 109.7(3) . . ?
C9 C4 H4 107.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.7(4) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C5 C6 C7 112.5(3) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7 107.6 . . ?
C8 C7 C6 110.0(3) . . ?
C8 C7 H7 107.6 . . ?
C8 C7 C10 113.3(4) . . ?
C10 C7 C6 110.6(4) . . ?
C10 C7 H7 107.6 . . ?
O2 C8 O3 104.9(3) . . ?
O2 C8 C7 110.6(3) . . ?
O2 C8 C9 110.6(3) . . ?
O3 C8 C7 108.4(3) . . ?
O3 C8 C9 109.5(3) . . ?
C7 C8 C9 112.5(4) . . ?
C4 C9 H9A 109.4 . . ?
C4 C9 H9B 109.4 . . ?
C8 C9 C4 111.1(3) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 H12A 110.5 . . ?
O2 C12 H12B 110.5 . . ?
O2 C12 C13 106.3(4) . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
O3 C13 C12 105.5(4) . . ?
O3 C13 H13A 110.6 . . ?
O3 C13 H13B 110.6 . . ?
C12 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
H13A C13 H13B 108.8 . . ?
C15 C14 S1 119.1(4) . . ?
C15 C14 C19 120.6(5) . . ?
C19 C14 S1 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(5) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 121.1 . . ?
C17 C16 C15 117.8(4) . . ?
C17 C16 H16 121.1 . . ?
F1 C17 C16 117.6(5) . . ?
F1 C17 C18 118.1(5) . . ?
C18 C17 C16 124.3(5) . . ?
C17 C18 H18 121.4 . . ?
C17 C18 C19 117.2(5) . . ?
C19 C18 H18 121.4 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.9(4) . . ?
C18 C19 H19 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 -110.4(4) . . . . ?
S1 C1 C3 C2 112.7(4) . . . . ?
S1 C1 C3 C4 -137.8(3) . . . . ?
S1 C1 C3 C11 8.3(5) . . . . ?
S1 C14 C15 C16 176.3(4) . . . . ?
S1 C14 C19 C18 -175.5(3) . . . . ?
F1 C17 C18 C19 -178.9(4) . . . . ?
O1 S1 C1 C2 -91.4(4) . . . . ?
O1 S1 C1 C3 -164.3(4) . . . . ?
O1 S1 C14 C15 145.0(4) . . . . ?
O1 S1 C14 C19 -37.7(4) . . . . ?
O2 C8 C9 C4 67.8(4) . . . . ?
O2 C12 C13 O3 2.0(6) . . . . ?
O3 C8 C9 C4 -177.1(3) . . . . ?
C1 S1 C14 C15 -105.4(4) . . . . ?
C1 S1 C14 C19 71.9(4) . . . . ?
C1 C2 C3 C4 -102.1(4) . . . . ?
C1 C2 C3 C11 111.2(4) . . . . ?
C1 C3 C4 C5 -151.0(3) . . . . ?
C1 C3 C4 C9 85.0(4) . . . . ?
C2 C1 C3 C4 109.5(4) . . . . ?
C2 C1 C3 C11 -104.4(4) . . . . ?
C2 C3 C4 C5 -84.9(5) . . . . ?
C2 C3 C4 C9 151.0(4) . . . . ?
C3 C4 C5 C6 178.0(3) . . . . ?
C3 C4 C9 C8 -176.5(3) . . . . ?
C4 C5 C6 C7 56.5(5) . . . . ?
C5 C4 C9 C8 57.3(4) . . . . ?
C5 C6 C7 C8 -53.6(5) . . . . ?
C5 C6 C7 C10 -179.5(4) . . . . ?
C6 C7 C8 O2 -70.8(4) . . . . ?
C6 C7 C8 O3 174.8(3) . . . . ?
C6 C7 C8 C9 53.5(4) . . . . ?
C7 C8 C9 C4 -56.5(4) . . . . ?
C8 O2 C12 C13 15.9(5) . . . . ?
C8 O3 C13 C12 -19.1(5) . . . . ?
C9 C4 C5 C6 -57.2(4) . . . . ?
C10 C7 C8 O2 53.6(4) . . . . ?
C10 C7 C8 O3 -60.8(4) . . . . ?
C10 C7 C8 C9 177.9(3) . . . . ?
C11 C3 C4 C5 61.7(5) . . . . ?
C11 C3 C4 C9 -62.4(5) . . . . ?
C12 O2 C8 O3 -27.7(4) . . . . ?
C12 O2 C8 C7 -144.4(4) . . . . ?
C12 O2 C8 C9 90.2(4) . . . . ?
C13 O3 C8 O2 28.9(4) . . . . ?
C13 O3 C8 C7 147.1(4) . . . . ?
C13 O3 C8 C9 -89.8(4) . . . . ?
C14 S1 C1 C2 158.4(3) . . . . ?
C14 S1 C1 C3 85.5(4) . . . . ?
C14 C15 C16 C17 -0.4(7) . . . . ?
C15 C14 C19 C18 1.7(6) . . . . ?
C15 C16 C17 F1 179.6(4) . . . . ?
C15 C16 C17 C18 1.1(8) . . . . ?
C16 C17 C18 C19 -0.4(8) . . . . ?
C17 C18 C19 C14 -1.0(7) . . . . ?
C19 C14 C15 C16 -0.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_250507yw_frg_1
_database_code_depnum_ccdc_archive 'CCDC 2450394'
loop_
_audit_author_name
_audit_author_address
'Liyan Yuwen'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2025-05-11 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_audit_creation_date             2025-05-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 F O3 S'
_chemical_formula_sum            'C19 H25 F O3 S'
_chemical_formula_weight         352.45
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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                   6.99140(10)
_cell_length_b                   8.3848(2)
_cell_length_c                   30.4141(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1782.92(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.902
_cell_measurement_theta_min      4.761
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1661 before and 0.0861 after correction.
The Ratio of minimum to maximum transmission is 0.7615.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19678
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.880
_diffrn_reflns_theta_min         4.760
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2491146
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3196
_reflns_number_total             3371
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.420
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.152
_refine_ls_abs_structure_details 
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.058(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.0705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0988
_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:
 C1(H1), C4(H4), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,
 H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.49176(8) 0.76925(6) 0.55198(2) 0.02151(18) Uani 1 1 d . . . . .
F1 F -0.0796(3) 0.9236(2) 0.68753(6) 0.0442(4) Uani 1 1 d . . . . .
O1 O 0.4774(3) 0.8893(2) 0.51550(6) 0.0303(4) Uani 1 1 d . . . . .
O2 O 0.6810(3) 0.5793(2) 0.67440(5) 0.0288(4) Uani 1 1 d . . . . .
O3 O 0.5007(3) 0.3954(2) 0.71172(5) 0.0325(4) Uani 1 1 d . . . . .
C1 C 0.4029(3) 0.5876(3) 0.53065(8) 0.0222(5) Uani 1 1 d . . . . .
H1 H 0.272931 0.591817 0.516991 0.027 Uiso 1 1 calc R U . . .
C2 C 0.5507(3) 0.4865(3) 0.50691(8) 0.0236(5) Uani 1 1 d . . . . .
H2A H 0.511493 0.433937 0.479198 0.028 Uiso 1 1 calc R U . . .
H2B H 0.685414 0.522809 0.507658 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4647(3) 0.4263(3) 0.54897(8) 0.0216(5) Uani 1 1 d . . . . .
C4 C 0.5938(3) 0.4227(3) 0.58934(7) 0.0212(5) Uani 1 1 d . . . . .
H4 H 0.662087 0.527385 0.590608 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7464(4) 0.2921(3) 0.58746(8) 0.0269(5) Uani 1 1 d . . . . .
H5A H 0.821699 0.302809 0.560055 0.032 Uiso 1 1 calc R U . . .
H5B H 0.684333 0.186008 0.587394 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8789(4) 0.3065(4) 0.62731(8) 0.0305(6) Uani 1 1 d . . . . .
H6A H 0.948482 0.409161 0.625584 0.037 Uiso 1 1 calc R U . . .
H6B H 0.974734 0.219717 0.626169 0.037 Uiso 1 1 calc R U . . .
C7 C 0.7729(4) 0.2981(3) 0.67141(8) 0.0298(6) Uani 1 1 d . . . . .
H7 H 0.715232 0.189356 0.673993 0.036 Uiso 1 1 calc R U . . .
C8 C 0.6098(4) 0.4195(3) 0.67236(8) 0.0250(5) Uani 1 1 d . . . . .
C9 C 0.4801(4) 0.4057(3) 0.63216(7) 0.0239(5) Uani 1 1 d . . . . .
H9A H 0.380771 0.489792 0.633438 0.029 Uiso 1 1 calc R U . . .
H9B H 0.414889 0.300933 0.632539 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3148(4) 0.2963(3) 0.54486(9) 0.0311(6) Uani 1 1 d . . . . .
H10A H 0.229227 0.300067 0.570348 0.047 Uiso 1 1 calc R U . . .
H10B H 0.377933 0.192017 0.543650 0.047 Uiso 1 1 calc R U . . .
H10C H 0.240567 0.312821 0.517913 0.047 Uiso 1 1 calc R U . . .
C11 C 0.9101(5) 0.3204(4) 0.70987(9) 0.0422(7) Uani 1 1 d . . . . .
H11A H 0.959614 0.429761 0.709714 0.063 Uiso 1 1 calc R U . . .
H11B H 1.016673 0.245169 0.707095 0.063 Uiso 1 1 calc R U . . .
H11C H 0.842238 0.300671 0.737537 0.063 Uiso 1 1 calc R U . . .
C12 C 0.6141(5) 0.6516(4) 0.71441(9) 0.0354(6) Uani 1 1 d . . . . .
H12A H 0.576010 0.763909 0.709533 0.043 Uiso 1 1 calc R U . . .
H12B H 0.713162 0.647518 0.737642 0.043 Uiso 1 1 calc R U . . .
C13 C 0.4443(5) 0.5501(4) 0.72625(9) 0.0364(7) Uani 1 1 d . . . . .
H13A H 0.420668 0.551389 0.758344 0.044 Uiso 1 1 calc R U . . .
H13B H 0.327652 0.586578 0.710783 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3076(4) 0.8126(3) 0.59151(8) 0.0222(5) Uani 1 1 d . . . . .
C15 C 0.1161(4) 0.7727(3) 0.58584(8) 0.0289(6) Uani 1 1 d . . . . .
H15 H 0.075104 0.720725 0.559736 0.035 Uiso 1 1 calc R U . . .
C16 C -0.0144(4) 0.8096(3) 0.61862(9) 0.0330(6) Uani 1 1 d . . . . .
H16 H -0.145294 0.781257 0.615600 0.040 Uiso 1 1 calc R U . . .
C17 C 0.0492(4) 0.8883(3) 0.65577(8) 0.0301(6) Uani 1 1 d . . . . .
C18 C 0.2365(5) 0.9314(4) 0.66161(9) 0.0387(7) Uani 1 1 d . . . . .
H18 H 0.275794 0.986865 0.687308 0.046 Uiso 1 1 calc R U . . .
C19 C 0.3671(4) 0.8922(4) 0.62909(9) 0.0334(6) Uani 1 1 d . . . . .
H19 H 0.497994 0.919976 0.632547 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.5014(18) . ?
S1 C1 1.768(2) . ?
S1 C14 1.799(2) . ?
F1 C17 1.353(3) . ?
O2 C8 1.430(3) . ?
O2 C12 1.438(3) . ?
O3 C8 1.434(3) . ?
O3 C13 1.426(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.519(3) . ?
C1 C3 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.501(3) . ?
C3 C4 1.524(3) . ?
C3 C10 1.517(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.530(3) . ?
C4 C9 1.532(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.530(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.534(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.529(4) . ?
C7 C11 1.524(4) . ?
C8 C9 1.527(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.504(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.390(4) . ?
C14 C19 1.388(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(4) . ?
C17 C18 1.370(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(4) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C1 106.45(11) . . ?
O1 S1 C14 108.10(11) . . ?
C1 S1 C14 99.66(12) . . ?
C8 O2 C12 108.6(2) . . ?
C13 O3 C8 106.10(19) . . ?
S1 C1 H1 116.2 . . ?
C2 C1 S1 114.59(17) . . ?
C2 C1 H1 116.2 . . ?
C2 C1 C3 59.10(15) . . ?
C3 C1 S1 122.03(17) . . ?
C3 C1 H1 116.2 . . ?
C1 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
H2A C2 H2B 114.8 . . ?
C3 C2 C1 60.66(16) . . ?
C3 C2 H2A 117.7 . . ?
C3 C2 H2B 117.7 . . ?
C2 C3 C1 60.24(16) . . ?
C2 C3 C4 117.14(19) . . ?
C2 C3 C10 116.6(2) . . ?
C4 C3 C1 118.7(2) . . ?
C10 C3 C1 114.3(2) . . ?
C10 C3 C4 117.5(2) . . ?
C3 C4 H4 107.2 . . ?
C3 C4 C5 113.40(19) . . ?
C3 C4 C9 112.29(19) . . ?
C5 C4 H4 107.2 . . ?
C5 C4 C9 109.10(19) . . ?
C9 C4 H4 107.2 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C4 C5 C6 109.6(2) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C5 C6 C7 113.4(2) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7 107.8 . . ?
C8 C7 C6 110.3(2) . . ?
C8 C7 H7 107.8 . . ?
C11 C7 C6 111.2(2) . . ?
C11 C7 H7 107.8 . . ?
C11 C7 C8 111.9(2) . . ?
O2 C8 O3 106.33(19) . . ?
O2 C8 C7 111.4(2) . . ?
O2 C8 C9 108.2(2) . . ?
O3 C8 C7 108.6(2) . . ?
O3 C8 C9 110.0(2) . . ?
C9 C8 C7 112.2(2) . . ?
C4 C9 H9A 109.3 . . ?
C4 C9 H9B 109.3 . . ?
C8 C9 C4 111.43(19) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 H12A 111.2 . . ?
O2 C12 H12B 111.2 . . ?
O2 C12 C13 102.8(2) . . ?
H12A C12 H12B 109.1 . . ?
C13 C12 H12A 111.2 . . ?
C13 C12 H12B 111.2 . . ?
O3 C13 C12 102.8(2) . . ?
O3 C13 H13A 111.2 . . ?
O3 C13 H13B 111.2 . . ?
C12 C13 H13A 111.2 . . ?
C12 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C15 C14 S1 123.9(2) . . ?
C19 C14 S1 115.7(2) . . ?
C19 C14 C15 120.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.9(3) . . ?
C17 C16 H16 120.6 . . ?
F1 C17 C16 118.3(2) . . ?
F1 C17 C18 119.1(2) . . ?
C18 C17 C16 122.6(2) . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.4(3) . . ?
C19 C18 H18 120.8 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.3(3) . . ?
C18 C19 H19 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 113.94(19) . . . . ?
S1 C1 C3 C2 -101.4(2) . . . . ?
S1 C1 C3 C4 5.2(3) . . . . ?
S1 C1 C3 C10 150.66(18) . . . . ?
S1 C14 C15 C16 179.1(2) . . . . ?
S1 C14 C19 C18 179.9(2) . . . . ?
F1 C17 C18 C19 179.0(3) . . . . ?
O1 S1 C1 C2 86.75(19) . . . . ?
O1 S1 C1 C3 154.42(18) . . . . ?
O1 S1 C14 C15 77.7(2) . . . . ?
O1 S1 C14 C19 -101.5(2) . . . . ?
O2 C8 C9 C4 67.1(2) . . . . ?
O2 C12 C13 O3 34.4(3) . . . . ?
O3 C8 C9 C4 -177.18(19) . . . . ?
C1 S1 C14 C15 -33.3(2) . . . . ?
C1 S1 C14 C19 147.5(2) . . . . ?
C1 C2 C3 C4 -109.1(2) . . . . ?
C1 C2 C3 C10 104.1(2) . . . . ?
C1 C3 C4 C5 -141.2(2) . . . . ?
C1 C3 C4 C9 94.5(3) . . . . ?
C2 C1 C3 C4 106.6(2) . . . . ?
C2 C1 C3 C10 -107.9(2) . . . . ?
C2 C3 C4 C5 -72.1(3) . . . . ?
C2 C3 C4 C9 163.7(2) . . . . ?
C3 C4 C5 C6 175.3(2) . . . . ?
C3 C4 C9 C8 -174.2(2) . . . . ?
C4 C5 C6 C7 57.1(3) . . . . ?
C5 C4 C9 C8 59.2(3) . . . . ?
C5 C6 C7 C8 -52.8(3) . . . . ?
C5 C6 C7 C11 -177.5(2) . . . . ?
C6 C7 C8 O2 -69.9(3) . . . . ?
C6 C7 C8 O3 173.3(2) . . . . ?
C6 C7 C8 C9 51.5(3) . . . . ?
C7 C8 C9 C4 -56.2(3) . . . . ?
C8 O2 C12 C13 -20.8(3) . . . . ?
C8 O3 C13 C12 -35.7(3) . . . . ?
C9 C4 C5 C6 -58.7(3) . . . . ?
C10 C3 C4 C5 74.4(3) . . . . ?
C10 C3 C4 C9 -49.8(3) . . . . ?
C11 C7 C8 O2 54.3(3) . . . . ?
C11 C7 C8 O3 -62.4(3) . . . . ?
C11 C7 C8 C9 175.8(2) . . . . ?
C12 O2 C8 O3 -0.5(3) . . . . ?
C12 O2 C8 C7 -118.7(2) . . . . ?
C12 O2 C8 C9 117.6(2) . . . . ?
C13 O3 C8 O2 23.3(3) . . . . ?
C13 O3 C8 C7 143.2(2) . . . . ?
C13 O3 C8 C9 -93.7(2) . . . . ?
C14 S1 C1 C2 -161.00(18) . . . . ?
C14 S1 C1 C3 -93.3(2) . . . . ?
C14 C15 C16 C17 1.4(4) . . . . ?
C15 C14 C19 C18 0.7(4) . . . . ?
C15 C16 C17 F1 -180.0(3) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
C17 C18 C19 C14 0.6(5) . . . . ?
C19 C14 C15 C16 -1.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_240715gl_1
_database_code_depnum_ccdc_archive 'CCDC 2450631'
loop_
_audit_author_name
_audit_author_address
'Liyan Yuwen'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2025-05-13 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_audit_creation_date             2024-07-15
_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         '2(C18 H20 O2 S)'
_chemical_formula_sum            'C36 H40 O4 S2'
_chemical_formula_weight         600.80
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.9180(3)
_cell_length_b                   8.0256(4)
_cell_length_c                   16.8884(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.632(2)
_cell_angle_gamma                90
_cell_volume                     793.04(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3947
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.881
_cell_measurement_theta_min      4.609
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    1.191
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.2690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1682 before and 0.1027 after correction.
The Ratio of minimum to maximum transmission is 0.3583.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7231
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.856
_diffrn_reflns_theta_min         4.608
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                2598
_reflns_number_total             2898
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 988 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.052
_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)+(0.0441P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1087
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), 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
S1 S 0.89627(13) 0.57309(11) 0.80855(5) 0.0297(2) Uani 1 1 d . . . . .
O1 O 1.1307(4) 0.5088(3) 0.80066(15) 0.0381(7) Uani 1 1 d . . . . .
O2 O 0.0826(4) 0.8532(4) 0.40377(14) 0.0400(7) Uani 1 1 d . . . . .
C1 C 0.8036(6) 0.6845(4) 0.7190(2) 0.0270(7) Uani 1 1 d . . . . .
H1 H 0.815401 0.622796 0.668385 0.032 Uiso 1 1 calc R U . . .
C2 C 0.6179(6) 0.8188(4) 0.7125(2) 0.0278(8) Uani 1 1 d . . . . .
C3 C 0.8663(6) 0.8672(5) 0.7187(2) 0.0295(8) Uani 1 1 d . . . . .
H3A H 0.940458 0.916969 0.769642 0.035 Uiso 1 1 calc R U . . .
H3B H 0.919577 0.912005 0.670074 0.035 Uiso 1 1 calc R U . . .
C4 C 0.4962(6) 0.8544(5) 0.7837(2) 0.0348(8) Uani 1 1 d . . . . .
H4A H 0.606430 0.849503 0.833180 0.052 Uiso 1 1 calc R U . . .
H4B H 0.376355 0.770997 0.785951 0.052 Uiso 1 1 calc R U . . .
H4C H 0.427399 0.965636 0.778085 0.052 Uiso 1 1 calc R U . . .
C5 C 0.7033(6) 0.3969(4) 0.7886(2) 0.0302(8) Uani 1 1 d . . . . .
H5A H 0.543020 0.436349 0.780999 0.036 Uiso 1 1 calc R U . . .
H5B H 0.730623 0.339961 0.738897 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7427(6) 0.2769(4) 0.8580(2) 0.0295(8) Uani 1 1 d . . . . .
C7 C 0.9389(6) 0.1778(5) 0.8709(2) 0.0358(9) Uani 1 1 d . . . . .
H7 H 1.049034 0.185215 0.835477 0.043 Uiso 1 1 calc R U . . .
C8 C 0.9733(7) 0.0683(7) 0.9352(2) 0.0520(11) Uani 1 1 d . . . . .
H8 H 1.105862 0.000026 0.943393 0.062 Uiso 1 1 calc R U . . .
C9 C 0.8167(8) 0.0588(7) 0.9869(2) 0.0576(13) Uani 1 1 d . . . . .
H9 H 0.841477 -0.016351 1.030847 0.069 Uiso 1 1 calc R U . . .
C10 C 0.6237(8) 0.1567(7) 0.9760(3) 0.0547(12) Uani 1 1 d . . . . .
H10 H 0.516599 0.150100 1.012563 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5861(7) 0.2656(5) 0.9111(2) 0.0402(9) Uani 1 1 d . . . . .
H11 H 0.452146 0.332494 0.903121 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4711(6) 0.8289(4) 0.6315(2) 0.0266(8) Uani 1 1 d . . . . .
C13 C 0.2806(6) 0.7267(4) 0.6129(2) 0.0278(7) Uani 1 1 d . . . . .
H13 H 0.242845 0.651231 0.652228 0.033 Uiso 1 1 calc R U . . .
C14 C 0.1442(6) 0.7319(4) 0.5386(2) 0.0285(8) Uani 1 1 d . . . . .
H14 H 0.013234 0.662382 0.527865 0.034 Uiso 1 1 calc R U . . .
C15 C 0.1999(6) 0.8391(5) 0.4802(2) 0.0314(8) Uani 1 1 d . . . . .
C16 C 0.3887(6) 0.9429(5) 0.4977(2) 0.0383(9) Uani 1 1 d . . . . .
H16 H 0.426613 1.017687 0.458146 0.046 Uiso 1 1 calc R U . . .
C17 C 0.5220(6) 0.9381(5) 0.5725(2) 0.0346(9) Uani 1 1 d . . . . .
H17 H 0.649957 1.010342 0.583706 0.042 Uiso 1 1 calc R U . . .
C18 C -0.1280(7) 0.7628(5) 0.3849(2) 0.0404(10) Uani 1 1 d . . . . .
H18A H -0.199171 0.789762 0.330216 0.061 Uiso 1 1 calc R U . . .
H18B H -0.231534 0.793895 0.422587 0.061 Uiso 1 1 calc R U . . .
H18C H -0.096926 0.642874 0.388998 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.505(3) . ?
S1 C1 1.771(3) . ?
S1 C5 1.817(4) . ?
O2 C15 1.376(4) . ?
O2 C18 1.436(5) . ?
C1 H1 1.0000 . ?
C1 C2 1.532(5) . ?
C1 C3 1.513(5) . ?
C2 C3 1.509(5) . ?
C2 C4 1.520(5) . ?
C2 C12 1.509(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.507(5) . ?
C6 C7 1.398(5) . ?
C6 C11 1.386(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.367(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(5) . ?
C12 C17 1.394(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(5) . ?
C15 C16 1.390(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C1 105.60(15) . . ?
O1 S1 C5 106.20(16) . . ?
C1 S1 C5 97.43(16) . . ?
C15 O2 C18 117.7(3) . . ?
S1 C1 H1 115.3 . . ?
C2 C1 S1 123.0(2) . . ?
C2 C1 H1 115.3 . . ?
C3 C1 S1 116.6(3) . . ?
C3 C1 H1 115.3 . . ?
C3 C1 C2 59.4(2) . . ?
C3 C2 C1 59.7(2) . . ?
C3 C2 C4 118.0(3) . . ?
C4 C2 C1 119.7(3) . . ?
C12 C2 C1 114.4(3) . . ?
C12 C2 C3 118.1(3) . . ?
C12 C2 C4 115.6(3) . . ?
C1 C3 H3A 117.7 . . ?
C1 C3 H3B 117.7 . . ?
C2 C3 C1 60.9(2) . . ?
C2 C3 H3A 117.7 . . ?
C2 C3 H3B 117.7 . . ?
H3A C3 H3B 114.8 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
S1 C5 H5A 109.8 . . ?
S1 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 S1 109.5(2) . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C7 C6 C5 120.8(3) . . ?
C11 C6 C5 120.3(3) . . ?
C11 C6 C7 118.9(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C6 C11 C10 120.5(4) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C2 120.7(3) . . ?
C13 C12 C17 117.7(3) . . ?
C17 C12 C2 121.7(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.9(3) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
O2 C15 C14 125.4(3) . . ?
O2 C15 C16 115.2(3) . . ?
C14 C15 C16 119.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 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
S1 C1 C2 C3 103.7(3) . . . . ?
S1 C1 C2 C4 -3.2(5) . . . . ?
S1 C1 C2 C12 -146.7(3) . . . . ?
S1 C1 C3 C2 -114.2(3) . . . . ?
S1 C5 C6 C7 -72.7(4) . . . . ?
S1 C5 C6 C11 106.1(3) . . . . ?
O1 S1 C1 C2 -158.1(3) . . . . ?
O1 S1 C1 C3 -88.8(3) . . . . ?
O1 S1 C5 C6 72.0(3) . . . . ?
O2 C15 C16 C17 -179.1(3) . . . . ?
C1 S1 C5 C6 -179.3(3) . . . . ?
C1 C2 C12 C13 85.6(4) . . . . ?
C1 C2 C12 C17 -93.5(4) . . . . ?
C2 C12 C13 C14 -179.2(3) . . . . ?
C2 C12 C17 C16 178.4(4) . . . . ?
C3 C1 C2 C4 -107.0(4) . . . . ?
C3 C1 C2 C12 109.5(3) . . . . ?
C3 C2 C12 C13 152.8(3) . . . . ?
C3 C2 C12 C17 -26.3(5) . . . . ?
C4 C2 C3 C1 109.8(4) . . . . ?
C4 C2 C12 C13 -59.4(4) . . . . ?
C4 C2 C12 C17 121.4(4) . . . . ?
C5 S1 C1 C2 92.7(3) . . . . ?
C5 S1 C1 C3 162.1(3) . . . . ?
C5 C6 C7 C8 179.7(4) . . . . ?
C5 C6 C11 C10 -179.0(4) . . . . ?
C6 C7 C8 C9 -0.9(7) . . . . ?
C7 C6 C11 C10 -0.2(6) . . . . ?
C7 C8 C9 C10 0.0(7) . . . . ?
C8 C9 C10 C11 0.7(7) . . . . ?
C9 C10 C11 C6 -0.6(6) . . . . ?
C11 C6 C7 C8 0.9(6) . . . . ?
C12 C2 C3 C1 -103.3(3) . . . . ?
C12 C13 C14 C15 1.3(5) . . . . ?
C13 C12 C17 C16 -0.8(5) . . . . ?
C13 C14 C15 O2 178.3(3) . . . . ?
C13 C14 C15 C16 -1.6(5) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C15 C16 C17 C12 0.4(6) . . . . ?
C17 C12 C13 C14 -0.1(5) . . . . ?
C18 O2 C15 C14 6.8(5) . . . . ?
C18 O2 C15 C16 -173.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_250515yw
_database_code_depnum_ccdc_archive 'CCDC 2451688'
loop_
_audit_author_name
_audit_author_address
'Liyan Yuwen'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_audit_creation_date             2025-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 O S'
_chemical_formula_sum            'C22 H26 O S'
_chemical_formula_weight         338.49
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   17.9220(5)
_cell_length_b                   17.9220(5)
_cell_length_c                   11.4729(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3191.4(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.23
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.860
_exptl_absorpt_coefficient_mu    0.916
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1682 before and 0.1078 after correction.
The Ratio of minimum to maximum transmission is 0.7018.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1481
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            42723
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.014
_diffrn_reflns_theta_min         4.169
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2491146
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3174
_reflns_number_total             4030
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.102(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4030
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1158
_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:
 C1(H1), C4(H4), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.49999(6) 0.96885(6) 0.42730(8) 0.0361(3) Uani 1 1 d . . . . .
O1 O 0.55718(18) 1.01777(19) 0.3265(2) 0.0465(7) Uani 1 1 d . . . . .
C1 C 0.4378(2) 1.0169(3) 0.4621(3) 0.0340(9) Uani 1 1 d . . . . .
H1 H 0.470001 1.077130 0.493030 0.041 Uiso 1 1 calc R U . . .
C2 C 0.3450(2) 0.9618(2) 0.5035(3) 0.0334(8) Uani 1 1 d . . . . .
C3 C 0.3630(3) 0.9963(3) 0.3810(3) 0.0407(10) Uani 1 1 d . . . . .
H3A H 0.351322 1.043353 0.361863 0.049 Uiso 1 1 calc R U . . .
H3B H 0.351553 0.954947 0.316867 0.049 Uiso 1 1 calc R U . . .
C4 C 0.3108(2) 1.0010(2) 0.5920(4) 0.0367(9) Uani 1 1 d . . . . .
H4 H 0.316406 0.980833 0.671104 0.044 Uiso 1 1 calc R U . . .
C5 C 0.2160(3) 0.9721(3) 0.5732(4) 0.0491(11) Uani 1 1 d . . . . .
H5A H 0.178823 0.912326 0.600944 0.059 Uiso 1 1 calc R U . . .
H5B H 0.203994 0.975013 0.489552 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1999(3) 1.0355(3) 0.6448(6) 0.0662(15) Uani 1 1 d . . . . .
H6A H 0.170177 1.008549 0.718826 0.079 Uiso 1 1 calc R U . . .
H6B H 0.164059 1.053241 0.600307 0.079 Uiso 1 1 calc R U . . .
C7 C 0.2902(3) 1.1138(3) 0.6690(4) 0.0560(12) Uani 1 1 d . . . . .
H7A H 0.292275 1.167988 0.645358 0.067 Uiso 1 1 calc R U . . .
H7B H 0.304362 1.117391 0.752943 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3531(3) 1.0991(3) 0.5967(4) 0.0455(10) Uani 1 1 d . . . . .
H8A H 0.410299 1.125194 0.634739 0.055 Uiso 1 1 calc R U . . .
H8B H 0.359930 1.123688 0.517536 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3094(2) 0.8664(2) 0.5210(3) 0.0316(8) Uani 1 1 d . . . . .
C10 C 0.3288(2) 0.8377(2) 0.6239(3) 0.0342(9) Uani 1 1 d . . . . .
H10 H 0.364670 0.878339 0.680896 0.041 Uiso 1 1 calc R U . . .
C11 C 0.2964(2) 0.7511(3) 0.6432(4) 0.0387(9) Uani 1 1 d . . . . .
H11 H 0.310871 0.732377 0.712683 0.046 Uiso 1 1 calc R U . . .
C12 C 0.2426(2) 0.6909(3) 0.5615(3) 0.0366(9) Uani 1 1 d . . . . .
H12 H 0.220247 0.631179 0.574984 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2219(3) 0.7183(3) 0.4615(3) 0.0381(10) Uani 1 1 d . . . . .
H13 H 0.184649 0.677323 0.405939 0.046 Uiso 1 1 calc R U . . .
C14 C 0.2551(2) 0.8057(2) 0.4408(3) 0.0377(9) Uani 1 1 d . . . . .
H14 H 0.240400 0.824011 0.371150 0.045 Uiso 1 1 calc R U . . .
C15 C 0.5688(3) 1.0001(3) 0.5577(3) 0.0379(9) Uani 1 1 d . . . . .
H15 H 0.530462 0.976519 0.627414 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6207(3) 0.9539(3) 0.5479(4) 0.0487(11) Uani 1 1 d . . . . .
H16A H 0.581423 0.891505 0.548271 0.073 Uiso 1 1 calc R U . . .
H16B H 0.660384 0.969952 0.614159 0.073 Uiso 1 1 calc R U . . .
H16C H 0.653729 0.970774 0.475112 0.073 Uiso 1 1 calc R U . . .
C17 C 0.6232(2) 1.0964(2) 0.5726(3) 0.0339(9) Uani 1 1 d . . . . .
C18 C 0.6003(3) 1.1376(3) 0.6560(3) 0.0362(9) Uani 1 1 d . . . . .
H18 H 0.549409 1.105213 0.700671 0.043 Uiso 1 1 calc R U . . .
C19 C 0.6514(3) 1.2261(3) 0.6749(3) 0.0393(9) Uani 1 1 d . . . . .
H19 H 0.635330 1.253656 0.732306 0.047 Uiso 1 1 calc R U . . .
C20 C 0.7250(3) 1.2734(3) 0.6100(3) 0.0401(10) Uani 1 1 d . . . . .
H20 H 0.760527 1.333479 0.623617 0.048 Uiso 1 1 calc R U . . .
C21 C 0.7472(3) 1.2333(3) 0.5251(4) 0.0435(10) Uani 1 1 d . . . . .
H21 H 0.797442 1.266249 0.479381 0.052 Uiso 1 1 calc R U . . .
C22 C 0.6967(3) 1.1454(3) 0.5060(4) 0.0386(9) Uani 1 1 d . . . . .
H22 H 0.712416 1.118484 0.447256 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.502(3) . ?
S1 C1 1.762(4) . ?
S1 C15 1.840(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.524(5) . ?
C1 C3 1.518(5) . ?
C2 C3 1.504(5) . ?
C2 C4 1.527(5) . ?
C2 C9 1.510(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4 1.0000 . ?
C4 C5 1.525(6) . ?
C4 C8 1.529(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.541(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.547(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.399(5) . ?
C9 C14 1.384(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.370(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(6) . ?
C14 H14 0.9500 . ?
C15 H15 1.0000 . ?
C15 C16 1.527(6) . ?
C15 C17 1.509(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.389(5) . ?
C17 C22 1.391(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(6) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C1 107.64(17) . . ?
O1 S1 C15 106.87(17) . . ?
C1 S1 C15 99.13(18) . . ?
S1 C1 H1 116.3 . . ?
C2 C1 S1 120.3(3) . . ?
C2 C1 H1 116.3 . . ?
C3 C1 S1 116.1(3) . . ?
C3 C1 H1 116.3 . . ?
C3 C1 C2 59.2(2) . . ?
C1 C2 C4 117.8(3) . . ?
C3 C2 C1 60.2(3) . . ?
C3 C2 C4 119.0(3) . . ?
C3 C2 C9 118.2(3) . . ?
C9 C2 C1 118.8(3) . . ?
C9 C2 C4 113.1(3) . . ?
C1 C3 H3A 117.7 . . ?
C1 C3 H3B 117.7 . . ?
C2 C3 C1 60.6(2) . . ?
C2 C3 H3A 117.7 . . ?
C2 C3 H3B 117.7 . . ?
H3A C3 H3B 114.8 . . ?
C2 C4 H4 107.6 . . ?
C2 C4 C8 118.1(3) . . ?
C5 C4 C2 112.7(3) . . ?
C5 C4 H4 107.6 . . ?
C5 C4 C8 102.8(3) . . ?
C8 C4 H4 107.6 . . ?
C4 C5 H5A 110.7 . . ?
C4 C5 H5B 110.7 . . ?
C4 C5 C6 105.2(4) . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 H5A 110.7 . . ?
C6 C5 H5B 110.7 . . ?
C5 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
C5 C6 C7 105.6(4) . . ?
H6A C6 H6B 108.8 . . ?
C7 C6 H6A 110.6 . . ?
C7 C6 H6B 110.6 . . ?
C6 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
C8 C7 C6 105.9(4) . . ?
C8 C7 H7A 110.6 . . ?
C8 C7 H7B 110.6 . . ?
C4 C8 H8A 111.1 . . ?
C4 C8 H8B 111.1 . . ?
C7 C8 C4 103.5(3) . . ?
C7 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.0 . . ?
C10 C9 C2 119.1(3) . . ?
C14 C9 C2 122.3(3) . . ?
C14 C9 C10 118.6(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(4) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.5(4) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
S1 C15 H15 107.9 . . ?
C16 C15 S1 105.8(3) . . ?
C16 C15 H15 107.9 . . ?
C17 C15 S1 113.0(3) . . ?
C17 C15 H15 107.9 . . ?
C17 C15 C16 114.1(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 119.6(3) . . ?
C18 C17 C22 118.7(4) . . ?
C22 C17 C15 121.7(3) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.7(4) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.8(4) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.5(4) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.3(4) . . ?
C21 C22 H22 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 -104.1(3) . . . . ?
S1 C1 C2 C4 146.7(3) . . . . ?
S1 C1 C2 C9 3.7(4) . . . . ?
S1 C1 C3 C2 111.3(3) . . . . ?
S1 C15 C17 C18 104.3(3) . . . . ?
S1 C15 C17 C22 -76.7(4) . . . . ?
O1 S1 C1 C2 144.5(3) . . . . ?
O1 S1 C1 C3 76.4(3) . . . . ?
O1 S1 C15 C16 -74.7(3) . . . . ?
O1 S1 C15 C17 50.9(3) . . . . ?
C1 S1 C15 C16 173.6(3) . . . . ?
C1 S1 C15 C17 -60.8(3) . . . . ?
C1 C2 C4 C5 144.6(3) . . . . ?
C1 C2 C4 C8 24.9(5) . . . . ?
C1 C2 C9 C10 80.7(4) . . . . ?
C1 C2 C9 C14 -102.2(4) . . . . ?
C2 C4 C5 C6 -164.7(3) . . . . ?
C2 C4 C8 C7 166.1(3) . . . . ?
C2 C9 C10 C11 179.1(4) . . . . ?
C2 C9 C14 C13 -178.4(3) . . . . ?
C3 C1 C2 C4 -109.2(4) . . . . ?
C3 C1 C2 C9 107.8(4) . . . . ?
C3 C2 C4 C5 75.1(4) . . . . ?
C3 C2 C4 C8 -44.6(5) . . . . ?
C3 C2 C9 C10 150.3(4) . . . . ?
C3 C2 C9 C14 -32.6(5) . . . . ?
C4 C2 C3 C1 107.3(4) . . . . ?
C4 C2 C9 C10 -64.0(4) . . . . ?
C4 C2 C9 C14 113.2(4) . . . . ?
C4 C5 C6 C7 17.7(5) . . . . ?
C5 C4 C8 C7 41.3(4) . . . . ?
C5 C6 C7 C8 7.9(5) . . . . ?
C6 C7 C8 C4 -30.4(5) . . . . ?
C8 C4 C5 C6 -36.5(4) . . . . ?
C9 C2 C3 C1 -108.9(4) . . . . ?
C9 C2 C4 C5 -70.4(4) . . . . ?
C9 C2 C4 C8 169.9(3) . . . . ?
C9 C10 C11 C12 -1.2(6) . . . . ?
C10 C9 C14 C13 -1.2(5) . . . . ?
C10 C11 C12 C13 0.0(6) . . . . ?
C11 C12 C13 C14 0.7(6) . . . . ?
C12 C13 C14 C9 -0.1(6) . . . . ?
C14 C9 C10 C11 1.8(5) . . . . ?
C15 S1 C1 C2 -104.4(3) . . . . ?
C15 S1 C1 C3 -172.5(3) . . . . ?
C15 C17 C18 C19 177.4(3) . . . . ?
C15 C17 C22 C21 -177.4(4) . . . . ?
C16 C15 C17 C18 -134.7(4) . . . . ?
C16 C15 C17 C22 44.4(5) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C17 C22 C21 1.7(6) . . . . ?
C18 C19 C20 C21 1.2(6) . . . . ?
C19 C20 C21 C22 -1.2(6) . . . . ?
C20 C21 C22 C17 -0.2(6) . . . . ?
C22 C17 C18 C19 -1.7(5) . . . . ?

_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 0.000 0.000 -0.901 650.6 241.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
