# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mo_b20220719bb_0m
_database_code_depnum_ccdc_archive 'CCDC 2192717'
loop_
_audit_author_name
_audit_author_address
'Sheng-suo Zhou'
;Soochow university
China
;
_audit_update_record             
;
2022-07-26 deposited with the CCDC.	2023-03-23 downloaded from the CCDC.
;
_audit_creation_date             2022-07-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 F N O2 S'
_chemical_formula_sum            'C23 H20 F N O2 S'
_chemical_formula_weight         393.46
_chemical_absolute_configuration ad
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   11.2213(4)
_cell_length_b                   10.9116(3)
_cell_length_c                   16.2561(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.3400(10)
_cell_angle_gamma                90
_cell_volume                     1951.58(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    119.97
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.982
_diffrn_reflns_theta_max         24.982
_diffrn_reflns_theta_min         2.262
_diffrn_ambient_temperature      119.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6046
_reflns_number_total             6875
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.233
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 2543 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6875
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.039
_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)+(0.0640P)²+1.1153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1252
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C37(H37), C8(H8), C36(H36)
2.b Aromatic/amide H refined with riding coordinates:
 C44(H44), C19(H19), C11(H11), C25(H25), C28(H28), C9(H9), C30(H30), C18(H18),
 C15(H15), C42(H42), C32(H32), C6(H6), C43(H43), C40(H40), C39(H39), C4(H4),
 C3(H3), C35(H35), C13(H13), C17(H17), C1(H1), C41(H41), C27(H27), C26(H26),
 C2(H2), C20(H20)
2.c X=CH2 refined with riding coordinates:
 C45(H45A,H45B), C46(H46A,H46B)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.52533(10) -0.51078(10) -0.99366(7) 0.0205(3) Uani 1 1 d . . . . .
S2 S -0.05087(10) -0.52793(11) -0.53608(7) 0.0238(3) Uani 1 1 d . . . . .
F2 F -0.3938(3) -0.1753(3) -0.50453(19) 0.0361(7) Uani 1 1 d . . . . .
F1 F -0.7375(3) -0.8695(3) -0.8253(2) 0.0462(9) Uani 1 1 d . . . . .
O2 O -0.5605(3) -0.6280(3) -1.0295(2) 0.0248(7) Uani 1 1 d . . . . .
O3 O -0.0642(3) -0.4128(3) -0.5785(2) 0.0285(8) Uani 1 1 d . . . . .
O1 O -0.5307(3) -0.4055(3) -1.0467(2) 0.0264(8) Uani 1 1 d . . . . .
O4 O 0.0661(3) -0.5838(3) -0.5126(2) 0.0306(8) Uani 1 1 d . . . . .
N2 N -0.6178(3) -0.4803(3) -0.9291(2) 0.0210(8) Uani 1 1 d . . . . .
N1 N -0.0991(3) -0.5057(4) -0.4473(2) 0.0230(8) Uani 1 1 d . . . . .
C31 C -0.3594(5) -0.2894(4) -0.4749(3) 0.0269(11) Uani 1 1 d . . . . .
C38 C -0.0053(4) -0.5826(4) -0.3079(3) 0.0231(10) Uani 1 1 d . . . . .
C24 C -0.3132(5) -0.8016(5) -0.6841(3) 0.0260(11) Uani 1 1 d . . . . .
C10 C -0.6429(4) -0.5091(4) -0.7926(3) 0.0231(10) Uani 1 1 d . . . . .
C5 C -0.7420(4) -0.2937(4) -0.9231(3) 0.0211(10) Uani 1 1 d . . . . .
C44 C -0.4024(4) -0.4700(5) -0.4047(3) 0.0293(11) Uani 1 1 d . . . . .
H44 H -0.455432 -0.517385 -0.378471 0.035 Uiso 1 1 calc R U . . .
C19 C -0.1885(5) -0.4281(5) -0.8721(3) 0.0294(11) Uani 1 1 d . . . . .
H19 H -0.138256 -0.357411 -0.862408 0.035 Uiso 1 1 calc R U . . .
C21 C -0.1435(4) -0.5398(5) -0.8384(3) 0.0291(11) Uani 1 1 d . . . . .
C11 C -0.6766(5) -0.5735(5) -0.7278(3) 0.0294(11) Uani 1 1 d . . . . .
H11 H -0.676979 -0.534196 -0.675724 0.035 Uiso 1 1 calc R U . . .
C25 C -0.1964(5) -0.8382(5) -0.6453(3) 0.0270(11) Uani 1 1 d . . . . .
H25 H -0.172193 -0.921062 -0.649334 0.032 Uiso 1 1 calc R U . . .
C12 C -0.6440(4) -0.5665(4) -0.8692(3) 0.0224(10) Uani 1 1 d . . . . .
C28 C -0.1155(4) -0.7545(5) -0.6011(3) 0.0249(11) Uani 1 1 d . . . . .
H28 H -0.036055 -0.780022 -0.575018 0.030 Uiso 1 1 calc R U . . .
C7 C -0.6201(4) -0.3550(4) -0.8925(3) 0.0213(10) Uani 1 1 d . . . . .
H7 H -0.553028 -0.303702 -0.906573 0.026 Uiso 1 1 calc R U . . .
C9 C -0.4679(5) -0.3643(5) -0.7532(3) 0.0287(11) Uani 1 1 d . . . . .
H9 H -0.410827 -0.419718 -0.768787 0.034 Uiso 1 1 calc R U . . .
C30 C -0.2453(4) -0.3294(4) -0.4820(3) 0.0248(11) Uani 1 1 d . . . . .
H30 H -0.192454 -0.281097 -0.507768 0.030 Uiso 1 1 calc R U . . .
C45 C -0.4268(6) -0.2814(5) -0.6962(4) 0.0403(14) Uani 1 1 d . . . . .
H45A H -0.481337 -0.224584 -0.679092 0.048 Uiso 1 1 calc R U . . .
H45B H -0.342653 -0.278294 -0.671916 0.048 Uiso 1 1 calc R U . . .
C14 C -0.7067(5) -0.7493(5) -0.8146(3) 0.0311(12) Uani 1 1 d . . . . .
C18 C -0.3052(5) -0.4176(4) -0.9195(3) 0.0254(11) Uani 1 1 d . . . . .
H18 H -0.335116 -0.340722 -0.942054 0.030 Uiso 1 1 calc R U . . .
C33 C -0.2881(4) -0.5139(5) -0.4095(3) 0.0244(10) Uani 1 1 d . . . . .
C15 C -0.7100(4) -0.6957(5) -0.7388(3) 0.0304(12) Uani 1 1 d . . . . .
H15 H -0.734414 -0.740932 -0.694984 0.036 Uiso 1 1 calc R U . . .
C42 C 0.0558(5) -0.4542(5) -0.1864(3) 0.0316(12) Uani 1 1 d . . . . .
H42 H 0.039736 -0.386770 -0.153251 0.038 Uiso 1 1 calc R U . . .
C37 C -0.0935(4) -0.6133(4) -0.3878(3) 0.0229(10) Uani 1 1 d . . . . .
H37 H -0.065053 -0.687927 -0.413923 0.027 Uiso 1 1 calc R U . . .
C32 C -0.4386(5) -0.3563(5) -0.4386(3) 0.0305(12) Uani 1 1 d . . . . .
H32 H -0.517086 -0.325153 -0.436670 0.037 Uiso 1 1 calc R U . . .
C16 C -0.3772(4) -0.5216(4) -0.9333(3) 0.0196(9) Uani 1 1 d . . . . .
C6 C -0.7506(5) -0.1683(4) -0.9091(3) 0.0273(11) Uani 1 1 d . . . . .
H6 H -0.680408 -0.123417 -0.883691 0.033 Uiso 1 1 calc R U . . .
C43 C -0.0268(4) -0.4851(4) -0.2586(3) 0.0278(11) Uani 1 1 d . . . . .
H43 H -0.099218 -0.438578 -0.274367 0.033 Uiso 1 1 calc R U . . .
C40 C 0.1828(5) -0.6204(5) -0.2105(3) 0.0324(12) Uani 1 1 d . . . . .
H40 H 0.254602 -0.667626 -0.193721 0.039 Uiso 1 1 calc R U . . .
C39 C 0.1003(4) -0.6516(5) -0.2826(3) 0.0280(11) Uani 1 1 d . . . . .
H39 H 0.115713 -0.720213 -0.314996 0.034 Uiso 1 1 calc R U . . .
C4 C -0.8445(4) -0.3569(5) -0.9599(3) 0.0262(11) Uani 1 1 d . . . . .
H4 H -0.839409 -0.442297 -0.970131 0.031 Uiso 1 1 calc R U . . .
C34 C -0.2127(4) -0.4446(4) -0.4492(3) 0.0229(10) Uani 1 1 d . . . . .
C3 C -0.9562(5) -0.2970(5) -0.9825(3) 0.0325(12) Uani 1 1 d . . . . .
H3 H -1.026649 -0.341710 -1.007583 0.039 Uiso 1 1 calc R U . . .
C35 C -0.2921(5) -0.7438(5) -0.4176(3) 0.0334(12) Uani 1 1 d . . . . .
H35 H -0.377513 -0.736050 -0.435861 0.040 Uiso 1 1 calc R U . . .
C8 C -0.5992(4) -0.3777(4) -0.7957(3) 0.0242(10) Uani 1 1 d . . . . .
H8 H -0.651393 -0.321346 -0.769539 0.029 Uiso 1 1 calc R U . . .
C13 C -0.6748(5) -0.6891(4) -0.8827(3) 0.0276(11) Uani 1 1 d . . . . .
H13 H -0.674072 -0.728957 -0.934531 0.033 Uiso 1 1 calc R U . . .
C17 C -0.3359(4) -0.6345(4) -0.9002(3) 0.0241(10) Uani 1 1 d . . . . .
H17 H -0.386434 -0.704985 -0.909791 0.029 Uiso 1 1 calc R U . . .
C1 C -0.8615(5) -0.1088(5) -0.9321(3) 0.0352(13) Uani 1 1 d . . . . .
H1 H -0.866780 -0.023156 -0.922887 0.042 Uiso 1 1 calc R U . . .
C41 C 0.1613(5) -0.5210(5) -0.1627(3) 0.0314(11) Uani 1 1 d . . . . .
H41 H 0.218815 -0.498936 -0.113908 0.038 Uiso 1 1 calc R U . . .
C29 C -0.1506(4) -0.6331(4) -0.5949(3) 0.0222(10) Uani 1 1 d . . . . .
C27 C -0.2677(5) -0.5962(4) -0.6323(3) 0.0269(11) Uani 1 1 d . . . . .
H27 H -0.292535 -0.513678 -0.627459 0.032 Uiso 1 1 calc R U . . .
C36 C -0.2275(4) -0.6328(4) -0.3759(3) 0.0257(11) Uani 1 1 d . . . . .
H36 H -0.227352 -0.637405 -0.314480 0.031 Uiso 1 1 calc R U . . .
C23 C -0.3986(5) -0.8916(5) -0.7361(3) 0.0318(12) Uani 1 1 d . . . . .
H23A H -0.390509 -0.885804 -0.794886 0.048 Uiso 1 1 calc R U . . .
H23B H -0.482438 -0.872505 -0.731596 0.048 Uiso 1 1 calc R U . . .
H23C H -0.378350 -0.974908 -0.715476 0.048 Uiso 1 1 calc R U . . .
C46 C -0.2462(5) -0.8482(5) -0.4318(4) 0.0390(14) Uani 1 1 d . . . . .
H46A H -0.161285 -0.861744 -0.415125 0.047 Uiso 1 1 calc R U . . .
H46B H -0.297393 -0.911493 -0.458988 0.047 Uiso 1 1 calc R U . . .
C26 C -0.3471(5) -0.6805(5) -0.6764(3) 0.0272(11) Uani 1 1 d . . . . .
H26 H -0.426724 -0.655115 -0.702081 0.033 Uiso 1 1 calc R U . . .
C2 C -0.9642(5) -0.1735(5) -0.9683(3) 0.0356(13) Uani 1 1 d . . . . .
H2 H -1.040156 -0.132718 -0.983364 0.043 Uiso 1 1 calc R U . . .
C20 C -0.2187(5) -0.6422(5) -0.8525(3) 0.0300(12) Uani 1 1 d . . . . .
H20 H -0.189377 -0.718800 -0.829153 0.036 Uiso 1 1 calc R U . . .
C22 C -0.0149(5) -0.5491(6) -0.7890(4) 0.0458(15) Uani 1 1 d . . . . .
H22A H 0.042308 -0.533721 -0.826293 0.069 Uiso 1 1 calc R U . . .
H22B H -0.001095 -0.631418 -0.764892 0.069 Uiso 1 1 calc R U . . .
H22C H -0.002437 -0.488222 -0.743813 0.069 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 O2 1.428(3) . ?
S1 O1 1.430(3) . ?
S1 N2 1.648(4) . ?
S1 C16 1.760(4) . ?
S2 O3 1.427(4) . ?
S2 O4 1.430(4) . ?
S2 N1 1.655(4) . ?
S2 C29 1.750(5) . ?
F2 C31 1.363(6) . ?
F1 C14 1.359(6) . ?
N2 C12 1.426(6) . ?
N2 C7 1.494(5) . ?
N1 C37 1.515(6) . ?
N1 C34 1.434(6) . ?
C31 C30 1.379(7) . ?
C31 C32 1.370(7) . ?
C38 C37 1.507(6) . ?
C38 C43 1.382(7) . ?
C38 C39 1.396(7) . ?
C24 C25 1.397(7) . ?
C24 C23 1.509(7) . ?
C24 C26 1.387(7) . ?
C10 C11 1.380(7) . ?
C10 C12 1.391(7) . ?
C10 C8 1.519(7) . ?
C5 C7 1.516(6) . ?
C5 C6 1.393(7) . ?
C5 C4 1.374(7) . ?
C44 H44 0.9500 . ?
C44 C33 1.386(7) . ?
C44 C32 1.386(7) . ?
C19 H19 0.9500 . ?
C19 C21 1.390(7) . ?
C19 C18 1.388(7) . ?
C21 C20 1.391(7) . ?
C21 C22 1.510(7) . ?
C11 H11 0.9500 . ?
C11 C15 1.386(7) . ?
C25 H25 0.9500 . ?
C25 C28 1.385(7) . ?
C12 C13 1.388(7) . ?
C28 H28 0.9500 . ?
C28 C29 1.391(7) . ?
C7 H7 1.0000 . ?
C7 C8 1.563(6) . ?
C9 H9 0.9500 . ?
C9 C45 1.312(7) . ?
C9 C8 1.507(7) . ?
C30 H30 0.9500 . ?
C30 C34 1.386(7) . ?
C45 H45A 0.9500 . ?
C45 H45B 0.9500 . ?
C14 C15 1.372(8) . ?
C14 C13 1.393(7) . ?
C18 H18 0.9500 . ?
C18 C16 1.386(7) . ?
C33 C34 1.385(7) . ?
C33 C36 1.515(7) . ?
C15 H15 0.9500 . ?
C42 H42 0.9500 . ?
C42 C43 1.386(7) . ?
C42 C41 1.380(7) . ?
C37 H37 1.0000 . ?
C37 C36 1.567(7) . ?
C32 H32 0.9500 . ?
C16 C17 1.387(6) . ?
C6 H6 0.9500 . ?
C6 C1 1.388(7) . ?
C43 H43 0.9500 . ?
C40 H40 0.9500 . ?
C40 C39 1.387(7) . ?
C40 C41 1.382(8) . ?
C39 H39 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.397(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.373(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.503(7) . ?
C35 C46 1.289(8) . ?
C8 H8 1.0000 . ?
C13 H13 0.9500 . ?
C17 H17 0.9500 . ?
C17 C20 1.392(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(8) . ?
C41 H41 0.9500 . ?
C29 C27 1.394(7) . ?
C27 H27 0.9500 . ?
C27 C26 1.380(7) . ?
C36 H36 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C46 H46A 0.9500 . ?
C46 H46B 0.9500 . ?
C26 H26 0.9500 . ?
C2 H2 0.9500 . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.86(19) . . ?
O2 S1 N2 106.4(2) . . ?
O2 S1 C16 108.8(2) . . ?
O1 S1 N2 105.3(2) . . ?
O1 S1 C16 108.3(2) . . ?
N2 S1 C16 107.6(2) . . ?
O3 S2 O4 120.6(2) . . ?
O3 S2 N1 105.7(2) . . ?
O3 S2 C29 108.6(2) . . ?
O4 S2 N1 105.7(2) . . ?
O4 S2 C29 108.7(2) . . ?
N1 S2 C29 106.8(2) . . ?
C12 N2 S1 122.8(3) . . ?
C12 N2 C7 108.0(3) . . ?
C7 N2 S1 120.0(3) . . ?
C37 N1 S2 117.6(3) . . ?
C34 N1 S2 119.5(3) . . ?
C34 N1 C37 107.4(4) . . ?
F2 C31 C30 117.5(5) . . ?
F2 C31 C32 118.4(4) . . ?
C32 C31 C30 124.0(5) . . ?
C43 C38 C37 120.7(4) . . ?
C43 C38 C39 118.6(4) . . ?
C39 C38 C37 120.6(4) . . ?
C25 C24 C23 120.2(5) . . ?
C26 C24 C25 118.7(5) . . ?
C26 C24 C23 121.0(5) . . ?
C11 C10 C12 119.9(5) . . ?
C11 C10 C8 130.1(4) . . ?
C12 C10 C8 110.0(4) . . ?
C6 C5 C7 117.8(4) . . ?
C4 C5 C7 123.1(4) . . ?
C4 C5 C6 119.0(5) . . ?
C33 C44 H44 120.4 . . ?
C33 C44 C32 119.3(5) . . ?
C32 C44 H44 120.4 . . ?
C21 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C21 121.4(5) . . ?
C19 C21 C20 118.5(4) . . ?
C19 C21 C22 120.2(5) . . ?
C20 C21 C22 121.2(5) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C15 119.9(5) . . ?
C15 C11 H11 120.0 . . ?
C24 C25 H25 119.7 . . ?
C28 C25 C24 120.5(5) . . ?
C28 C25 H25 119.7 . . ?
C10 C12 N2 110.3(4) . . ?
C13 C12 N2 127.3(5) . . ?
C13 C12 C10 122.2(5) . . ?
C25 C28 H28 120.0 . . ?
C25 C28 C29 119.9(4) . . ?
C29 C28 H28 120.0 . . ?
N2 C7 C5 111.0(4) . . ?
N2 C7 H7 110.4 . . ?
N2 C7 C8 104.2(3) . . ?
C5 C7 H7 110.4 . . ?
C5 C7 C8 110.3(4) . . ?
C8 C7 H7 110.4 . . ?
C45 C9 H9 117.8 . . ?
C45 C9 C8 124.5(5) . . ?
C8 C9 H9 117.8 . . ?
C31 C30 H30 122.2 . . ?
C31 C30 C34 115.7(5) . . ?
C34 C30 H30 122.2 . . ?
C9 C45 H45A 120.0 . . ?
C9 C45 H45B 120.0 . . ?
H45A C45 H45B 120.0 . . ?
F1 C14 C15 118.4(5) . . ?
F1 C14 C13 116.9(5) . . ?
C15 C14 C13 124.7(5) . . ?
C19 C18 H18 120.7 . . ?
C16 C18 C19 118.6(4) . . ?
C16 C18 H18 120.7 . . ?
C44 C33 C34 119.6(5) . . ?
C44 C33 C36 129.1(5) . . ?
C34 C33 C36 111.3(4) . . ?
C11 C15 H15 120.9 . . ?
C14 C15 C11 118.1(5) . . ?
C14 C15 H15 120.9 . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C41 C42 C43 120.1(5) . . ?
N1 C37 H37 109.6 . . ?
N1 C37 C36 105.3(4) . . ?
C38 C37 N1 108.4(4) . . ?
C38 C37 H37 109.6 . . ?
C38 C37 C36 114.1(4) . . ?
C36 C37 H37 109.6 . . ?
C31 C32 C44 118.9(5) . . ?
C31 C32 H32 120.5 . . ?
C44 C32 H32 120.5 . . ?
C18 C16 S1 119.5(4) . . ?
C18 C16 C17 121.6(4) . . ?
C17 C16 S1 118.9(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 C5 120.2(5) . . ?
C1 C6 H6 119.9 . . ?
C38 C43 C42 121.0(5) . . ?
C38 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C41 C40 C39 120.5(5) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 C38 120.2(5) . . ?
C40 C39 H39 119.9 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.7(5) . . ?
C3 C4 H4 119.7 . . ?
C30 C34 N1 126.6(4) . . ?
C33 C34 N1 111.0(4) . . ?
C33 C34 C30 122.4(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0(5) . . ?
C2 C3 H3 120.0 . . ?
C36 C35 H35 115.9 . . ?
C46 C35 H35 115.9 . . ?
C46 C35 C36 128.2(5) . . ?
C10 C8 C7 101.4(4) . . ?
C10 C8 H8 110.3 . . ?
C7 C8 H8 110.3 . . ?
C9 C8 C10 111.6(4) . . ?
C9 C8 C7 112.7(4) . . ?
C9 C8 H8 110.3 . . ?
C12 C13 C14 115.1(5) . . ?
C12 C13 H13 122.5 . . ?
C14 C13 H13 122.5 . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C20 118.5(5) . . ?
C20 C17 H17 120.8 . . ?
C6 C1 H1 119.9 . . ?
C2 C1 C6 120.3(5) . . ?
C2 C1 H1 119.9 . . ?
C42 C41 C40 119.5(4) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
C28 C29 S2 120.3(4) . . ?
C28 C29 C27 120.0(4) . . ?
C27 C29 S2 119.7(4) . . ?
C29 C27 H27 120.3 . . ?
C26 C27 C29 119.4(4) . . ?
C26 C27 H27 120.3 . . ?
C33 C36 C37 102.3(4) . . ?
C33 C36 H36 108.4 . . ?
C37 C36 H36 108.4 . . ?
C35 C36 C33 112.6(4) . . ?
C35 C36 C37 116.3(4) . . ?
C35 C36 H36 108.4 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C35 C46 H46A 120.0 . . ?
C35 C46 H46B 120.0 . . ?
H46A C46 H46B 120.0 . . ?
C24 C26 H26 119.3 . . ?
C27 C26 C24 121.5(5) . . ?
C27 C26 H26 119.3 . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C21 C20 C17 121.3(5) . . ?
C21 C20 H20 119.3 . . ?
C17 C20 H20 119.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N2 C12 C10 136.9(3) . . . . ?
S1 N2 C12 C13 -47.1(6) . . . . ?
S1 N2 C7 C5 115.0(4) . . . . ?
S1 N2 C7 C8 -126.3(3) . . . . ?
S1 C16 C17 C20 -180.0(4) . . . . ?
S2 N1 C37 C38 115.7(4) . . . . ?
S2 N1 C37 C36 -121.8(3) . . . . ?
S2 N1 C34 C30 -56.2(6) . . . . ?
S2 N1 C34 C33 126.5(4) . . . . ?
S2 C29 C27 C26 -178.0(4) . . . . ?
F2 C31 C30 C34 178.4(4) . . . . ?
F2 C31 C32 C44 -177.0(4) . . . . ?
F1 C14 C15 C11 179.0(5) . . . . ?
F1 C14 C13 C12 180.0(4) . . . . ?
O2 S1 N2 C12 47.7(4) . . . . ?
O2 S1 N2 C7 -169.3(3) . . . . ?
O2 S1 C16 C18 154.9(4) . . . . ?
O2 S1 C16 C17 -25.6(4) . . . . ?
O3 S2 N1 C37 -179.0(3) . . . . ?
O3 S2 N1 C34 48.0(4) . . . . ?
O3 S2 C29 C28 142.2(4) . . . . ?
O3 S2 C29 C27 -40.8(4) . . . . ?
O1 S1 N2 C12 176.0(4) . . . . ?
O1 S1 N2 C7 -41.1(4) . . . . ?
O1 S1 C16 C18 23.1(4) . . . . ?
O1 S1 C16 C17 -157.3(3) . . . . ?
O4 S2 N1 C37 -50.1(4) . . . . ?
O4 S2 N1 C34 176.8(3) . . . . ?
O4 S2 C29 C28 9.3(5) . . . . ?
O4 S2 C29 C27 -173.7(4) . . . . ?
N2 S1 C16 C18 -90.2(4) . . . . ?
N2 S1 C16 C17 89.3(4) . . . . ?
N2 C12 C13 C14 -174.3(5) . . . . ?
N2 C7 C8 C10 -24.0(4) . . . . ?
N2 C7 C8 C9 95.5(4) . . . . ?
N1 S2 C29 C28 -104.2(4) . . . . ?
N1 S2 C29 C27 72.8(4) . . . . ?
N1 C37 C36 C33 -15.4(4) . . . . ?
N1 C37 C36 C35 107.8(4) . . . . ?
C31 C30 C34 N1 -178.8(4) . . . . ?
C31 C30 C34 C33 -1.8(7) . . . . ?
C38 C37 C36 C33 103.3(4) . . . . ?
C38 C37 C36 C35 -133.5(4) . . . . ?
C24 C25 C28 C29 0.2(7) . . . . ?
C10 C11 C15 C14 0.8(7) . . . . ?
C10 C12 C13 C14 1.3(7) . . . . ?
C5 C7 C8 C10 95.2(4) . . . . ?
C5 C7 C8 C9 -145.4(4) . . . . ?
C5 C6 C1 C2 0.6(8) . . . . ?
C5 C4 C3 C2 0.4(8) . . . . ?
C44 C33 C34 N1 179.9(4) . . . . ?
C44 C33 C34 C30 2.5(7) . . . . ?
C44 C33 C36 C37 -169.8(5) . . . . ?
C44 C33 C36 C35 64.6(6) . . . . ?
C19 C21 C20 C17 0.9(8) . . . . ?
C19 C18 C16 S1 -179.7(4) . . . . ?
C19 C18 C16 C17 0.7(7) . . . . ?
C21 C19 C18 C16 -0.2(7) . . . . ?
C11 C10 C12 N2 174.3(4) . . . . ?
C11 C10 C12 C13 -2.0(7) . . . . ?
C11 C10 C8 C7 -161.8(5) . . . . ?
C11 C10 C8 C9 78.0(6) . . . . ?
C25 C24 C26 C27 0.7(8) . . . . ?
C25 C28 C29 S2 177.8(4) . . . . ?
C25 C28 C29 C27 0.8(7) . . . . ?
C12 N2 C7 C5 -97.2(4) . . . . ?
C12 N2 C7 C8 21.5(5) . . . . ?
C12 C10 C11 C15 0.9(7) . . . . ?
C12 C10 C8 C7 19.3(5) . . . . ?
C12 C10 C8 C9 -100.8(5) . . . . ?
C28 C29 C27 C26 -1.0(7) . . . . ?
C7 N2 C12 C10 -9.8(5) . . . . ?
C7 N2 C12 C13 166.2(5) . . . . ?
C7 C5 C6 C1 -176.8(5) . . . . ?
C7 C5 C4 C3 176.2(5) . . . . ?
C30 C31 C32 C44 1.7(8) . . . . ?
C45 C9 C8 C10 -129.6(6) . . . . ?
C45 C9 C8 C7 117.1(6) . . . . ?
C18 C19 C21 C20 -0.6(8) . . . . ?
C18 C19 C21 C22 178.3(5) . . . . ?
C18 C16 C17 C20 -0.4(7) . . . . ?
C33 C44 C32 C31 -1.0(7) . . . . ?
C15 C14 C13 C12 0.5(8) . . . . ?
C37 N1 C34 C30 166.5(4) . . . . ?
C37 N1 C34 C33 -10.8(5) . . . . ?
C37 C38 C43 C42 -178.1(5) . . . . ?
C37 C38 C39 C40 178.0(4) . . . . ?
C32 C31 C30 C34 -0.3(7) . . . . ?
C32 C44 C33 C34 -1.0(7) . . . . ?
C32 C44 C33 C36 178.5(5) . . . . ?
C16 S1 N2 C12 -68.7(4) . . . . ?
C16 S1 N2 C7 74.2(4) . . . . ?
C16 C17 C20 C21 -0.4(7) . . . . ?
C6 C5 C7 N2 -166.8(4) . . . . ?
C6 C5 C7 C8 78.2(5) . . . . ?
C6 C5 C4 C3 -0.5(7) . . . . ?
C6 C1 C2 C3 -0.8(8) . . . . ?
C43 C38 C37 N1 62.5(5) . . . . ?
C43 C38 C37 C36 -54.4(6) . . . . ?
C43 C38 C39 C40 -1.5(7) . . . . ?
C43 C42 C41 C40 -1.3(8) . . . . ?
C39 C38 C37 N1 -117.1(5) . . . . ?
C39 C38 C37 C36 126.0(5) . . . . ?
C39 C38 C43 C42 1.5(7) . . . . ?
C39 C40 C41 C42 1.2(8) . . . . ?
C4 C5 C7 N2 16.5(6) . . . . ?
C4 C5 C7 C8 -98.5(5) . . . . ?
C4 C5 C6 C1 0.0(7) . . . . ?
C4 C3 C2 C1 0.3(8) . . . . ?
C34 N1 C37 C38 -106.1(4) . . . . ?
C34 N1 C37 C36 16.4(4) . . . . ?
C34 C33 C36 C37 9.7(5) . . . . ?
C34 C33 C36 C35 -115.9(5) . . . . ?
C8 C10 C11 C15 -177.8(5) . . . . ?
C8 C10 C12 N2 -6.8(5) . . . . ?
C8 C10 C12 C13 177.0(4) . . . . ?
C13 C14 C15 C11 -1.5(8) . . . . ?
C41 C42 C43 C38 -0.1(8) . . . . ?
C41 C40 C39 C38 0.2(8) . . . . ?
C29 S2 N1 C37 65.5(3) . . . . ?
C29 S2 N1 C34 -67.5(4) . . . . ?
C29 C27 C26 C24 0.3(8) . . . . ?
C36 C33 C34 N1 0.3(5) . . . . ?
C36 C33 C34 C30 -177.1(4) . . . . ?
C23 C24 C25 C28 176.8(5) . . . . ?
C23 C24 C26 C27 -177.0(5) . . . . ?
C46 C35 C36 C33 148.8(6) . . . . ?
C46 C35 C36 C37 31.2(8) . . . . ?
C26 C24 C25 C28 -0.9(7) . . . . ?
C22 C21 C20 C17 -178.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
