# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_11_a_pl
_database_code_depnum_ccdc_archive 'CCDC 2083910'
loop_
_audit_author_name
_audit_author_address
'xinrui dong'
;State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, School of Pharmacy 
China
;
_audit_update_record             
;
2021-05-15 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 F3 O4 S'
_chemical_formula_sum            'C12 H13 F3 O4 S'
_chemical_formula_weight         310.28
_chemical_absolute_configuration ?
_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'
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                   10.086(2)
_cell_length_b                   5.508(2)
_cell_length_c                   12.766(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.14(3)
_cell_angle_gamma                90
_cell_volume                     674.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2597
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      3.08
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1438 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.7433.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5559
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.125
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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_standards_number         0
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1920
_reflns_number_total             2333
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0807P)²+0.4283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1614
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(2)
 0.1(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4), C3(H3)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.21235(14) 0.5203(3) 0.58067(10) 0.0484(4) Uani 1 1 d . . . . .
F1 F -0.0360(4) 1.1726(7) 0.8163(3) 0.0682(11) Uani 1 1 d . . . . .
F3 F 0.0788(3) 0.8581(9) 0.8903(3) 0.0677(11) Uani 1 1 d . . . . .
F2 F -0.0900(4) 0.9795(9) 0.9402(3) 0.0732(13) Uani 1 1 d . . . . .
O1 O -0.2317(5) 0.6568(11) 0.4727(4) 0.0733(14) Uani 1 1 d . . . . .
O2 O -0.1182(6) 0.3293(12) 0.5708(5) 0.0880(17) Uani 1 1 d . . . . .
O3 O -0.3307(5) 0.4461(13) 0.6016(4) 0.088(2) Uani 1 1 d . . . . .
O4 O -0.6622(4) 0.6129(9) 0.8390(3) 0.0588(13) Uani 1 1 d . . . . .
C1 C -0.1482(4) 0.7945(9) 0.7660(4) 0.0327(10) Uani 1 1 d . . . . .
C2 C -0.1092(4) 0.7238(11) 0.6809(4) 0.0386(11) Uani 1 1 d . . . . .
C8 C -0.2831(4) 0.7409(10) 0.7864(4) 0.0343(10) Uani 1 1 d . . . . .
C7 C -0.2932(5) 0.5524(11) 0.8534(4) 0.0422(12) Uani 1 1 d . . . . .
H7 H -0.2154 0.4560 0.8854 0.051 Uiso 1 1 calc R U . . .
C6 C -0.4179(5) 0.5024(12) 0.8744(4) 0.0423(11) Uani 1 1 d . . . . .
H6 H -0.4237 0.3750 0.9206 0.051 Uiso 1 1 calc R U . . .
C5 C -0.5324(5) 0.6452(12) 0.8255(4) 0.0409(12) Uani 1 1 d . . . . .
C4 C -0.5233(5) 0.8407(12) 0.7597(4) 0.0452(13) Uani 1 1 d . . . . .
H4 H -0.6004 0.9393 0.7288 0.054 Uiso 1 1 calc R U . . .
C3 C -0.3989(5) 0.8869(11) 0.7406(4) 0.0416(12) Uani 1 1 d . . . . .
H3 H -0.3922 1.0178 0.6965 0.050 Uiso 1 1 calc R U . . .
C10 C -0.0478(6) 0.9518(12) 0.8537(4) 0.0457(13) Uani 1 1 d . . . . .
C11 C 0.0234(5) 0.7866(15) 0.6571(5) 0.0567(18) Uani 1 1 d . . . . .
H11A H 0.0859 0.6505 0.6748 0.085 Uiso 1 1 calc R U . . .
H11B H 0.0665 0.9238 0.7010 0.085 Uiso 1 1 calc R U . . .
H11C H 0.0027 0.8259 0.5805 0.085 Uiso 1 1 calc R U . . .
C12 C -0.3386(7) 0.8558(16) 0.4497(7) 0.088(3) Uani 1 1 d . . . . .
H12A H -0.2924 1.0098 0.4677 0.132 Uiso 1 1 calc R U . . .
H12B H -0.3992 0.8314 0.4937 0.132 Uiso 1 1 calc R U . . .
H12C H -0.3924 0.8536 0.3731 0.132 Uiso 1 1 calc R U . . .
C9 C -0.6784(6) 0.4143(16) 0.9049(6) 0.0674(19) Uani 1 1 d . . . . .
H9A H -0.6509 0.2670 0.8772 0.101 Uiso 1 1 calc R U . . .
H9B H -0.7744 0.4024 0.9023 0.101 Uiso 1 1 calc R U . . .
H9C H -0.6210 0.4393 0.9797 0.101 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 1.529(5) . ?
S1 O2 1.449(6) . ?
S1 O3 1.364(5) . ?
S1 C2 1.774(5) . ?
F1 C10 1.325(8) . ?
F3 C10 1.321(6) . ?
F2 C10 1.310(6) . ?
O1 C12 1.501(9) . ?
O4 C5 1.384(5) . ?
O4 C9 1.420(8) . ?
C1 C2 1.324(6) . ?
C1 C8 1.493(6) . ?
C1 C10 1.524(7) . ?
C2 C11 1.501(6) . ?
C8 C7 1.369(7) . ?
C8 C3 1.388(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.394(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.376(7) . ?
C5 C4 1.387(8) . ?
C4 H4 0.9300 . ?
C4 C3 1.374(7) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C2 102.8(3) . . ?
O2 S1 O1 100.5(3) . . ?
O2 S1 C2 105.6(3) . . ?
O3 S1 O1 116.8(3) . . ?
O3 S1 O2 115.9(4) . . ?
O3 S1 C2 113.6(3) . . ?
C12 O1 S1 114.7(5) . . ?
C5 O4 C9 117.4(4) . . ?
C2 C1 C8 127.2(4) . . ?
C2 C1 C10 118.1(4) . . ?
C8 C1 C10 114.7(4) . . ?
C1 C2 S1 121.4(4) . . ?
C1 C2 C11 127.5(5) . . ?
C11 C2 S1 111.1(4) . . ?
C7 C8 C1 120.5(4) . . ?
C7 C8 C3 119.1(4) . . ?
C3 C8 C1 120.4(5) . . ?
C8 C7 H7 119.4 . . ?
C8 C7 C6 121.2(5) . . ?
C6 C7 H7 119.4 . . ?
C7 C6 H6 120.7 . . ?
C5 C6 C7 118.7(5) . . ?
C5 C6 H6 120.7 . . ?
O4 C5 C4 114.8(5) . . ?
C6 C5 O4 124.2(5) . . ?
C6 C5 C4 121.0(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C8 C3 H3 119.6 . . ?
C4 C3 C8 120.9(5) . . ?
C4 C3 H3 119.6 . . ?
F1 C10 C1 111.7(4) . . ?
F3 C10 F1 107.5(5) . . ?
F3 C10 C1 112.7(5) . . ?
F2 C10 F1 106.6(5) . . ?
F2 C10 F3 106.2(5) . . ?
F2 C10 C1 111.7(4) . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O1 S1 C2 C1 126.3(5) . . . . ?
O1 S1 C2 C11 -56.4(5) . . . . ?
O2 S1 O1 C12 173.5(5) . . . . ?
O2 S1 C2 C1 -128.8(5) . . . . ?
O2 S1 C2 C11 48.5(5) . . . . ?
O3 S1 O1 C12 47.3(6) . . . . ?
O3 S1 C2 C1 -0.8(6) . . . . ?
O3 S1 C2 C11 176.5(5) . . . . ?
O4 C5 C4 C3 -179.5(5) . . . . ?
C1 C8 C7 C6 179.0(5) . . . . ?
C1 C8 C3 C4 -179.4(5) . . . . ?
C2 S1 O1 C12 -77.7(5) . . . . ?
C2 C1 C8 C7 96.8(6) . . . . ?
C2 C1 C8 C3 -85.5(7) . . . . ?
C2 C1 C10 F1 69.8(6) . . . . ?
C2 C1 C10 F3 -51.4(7) . . . . ?
C2 C1 C10 F2 -170.9(5) . . . . ?
C8 C1 C2 S1 -6.3(8) . . . . ?
C8 C1 C2 C11 176.9(5) . . . . ?
C8 C1 C10 F1 -109.3(5) . . . . ?
C8 C1 C10 F3 129.6(5) . . . . ?
C8 C1 C10 F2 10.1(7) . . . . ?
C8 C7 C6 C5 0.6(8) . . . . ?
C7 C8 C3 C4 -1.6(8) . . . . ?
C7 C6 C5 O4 179.4(5) . . . . ?
C7 C6 C5 C4 -2.3(8) . . . . ?
C6 C5 C4 C3 2.0(8) . . . . ?
C5 C4 C3 C8 0.0(8) . . . . ?
C3 C8 C7 C6 1.3(8) . . . . ?
C10 C1 C2 S1 174.7(4) . . . . ?
C10 C1 C2 C11 -2.1(9) . . . . ?
C10 C1 C8 C7 -84.2(6) . . . . ?
C10 C1 C8 C3 93.5(6) . . . . ?
C9 O4 C5 C6 -2.1(8) . . . . ?
C9 O4 C5 C4 179.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(2)
2 0.1(2)

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

data_exp_1870
_database_code_depnum_ccdc_archive 'CCDC 2083911'
loop_
_audit_author_name
_audit_author_address
'xinrui dong'
;State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, School of Pharmacy 
China
;
_audit_update_record             
;
2021-05-19 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 F3 O3 S'
_chemical_formula_sum            'C14 H17 F3 O3 S'
_chemical_formula_weight         322.33
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8048(3)
_cell_length_b                   12.4774(5)
_cell_length_c                   17.3856(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.185(3)
_cell_angle_gamma                90
_cell_volume                     1473.87(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8301
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      29.9190
_cell_measurement_theta_min      3.4110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25409
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.265
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00 -51.00   1.00    4.00    --    0.20 -57.00   0.00   25
  2  ω     46.00  72.00   1.00    4.00    --    0.20  57.00-180.00   26
  3  ω    -16.00  17.00   1.00    4.00    --    0.20  38.00 -60.00   33
  4  ω     24.00  90.00   1.00    4.00    --    0.20  38.00 -60.00   66
  5  ω    -89.00  -9.00   1.00    4.00    --    0.20 -57.00  60.00   80
  6  ω     -4.00  24.00   1.00    4.00    --    0.20 -57.00  60.00   28
  7  ω    -34.00  31.00   1.00    4.00    --    0.20 -77.00-150.00   65
  8  ω    -18.00  80.00   1.00    4.00    --    0.20  38.00  30.00   98
  9  ω    -15.00  10.00   1.00    4.00    --    0.20 -38.00   0.00   25
 10  ω     -4.00  21.00   1.00    4.00    --    0.20 -24.00 152.28   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0368824000
_diffrn_orient_matrix_UB_12      -0.0312840000
_diffrn_orient_matrix_UB_13      0.0316874000
_diffrn_orient_matrix_UB_21      -0.0021476000
_diffrn_orient_matrix_UB_22      0.0456935000
_diffrn_orient_matrix_UB_23      0.0241957000
_diffrn_orient_matrix_UB_31      -0.0976291000
_diffrn_orient_matrix_UB_32      -0.0128207000
_diffrn_orient_matrix_UB_33      0.0089917000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2946
_reflns_number_total             3377
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.071
_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     194
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.2975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), 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 0.94465(4) 0.71460(3) 0.47280(2) 0.02439(11) Uani 1 1 d . . . . .
F1 F 0.99349(13) 0.53758(7) 0.36269(5) 0.0374(2) Uani 1 1 d . . . . .
F3 F 0.79677(15) 0.51133(7) 0.26486(5) 0.0431(2) Uani 1 1 d . . . . .
F2 F 0.69164(15) 0.48947(7) 0.37772(6) 0.0420(2) Uani 1 1 d . . . . .
O3 O 0.87842(14) 0.59933(7) 0.49442(5) 0.0292(2) Uani 1 1 d . . . . .
O2 O 0.88137(15) 0.78601(8) 0.53076(5) 0.0309(2) Uani 1 1 d . . . . .
O1 O 1.14876(14) 0.70710(9) 0.45962(6) 0.0370(3) Uani 1 1 d . . . . .
C8 C 0.73989(17) 0.66866(9) 0.33491(6) 0.0205(2) Uani 1 1 d . . . . .
C1 C 0.57806(18) 0.68606(9) 0.27432(7) 0.0213(2) Uani 1 1 d . . . . .
C7 C 0.80479(17) 0.74692(10) 0.38397(7) 0.0201(2) Uani 1 1 d . . . . .
C10 C 0.7724(2) 0.86982(10) 0.37350(7) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.38940(19) 0.70081(10) 0.29925(8) 0.0260(3) Uani 1 1 d . . . . .
H2 H 0.367742 0.698505 0.351575 0.031 Uiso 1 1 calc R . . . .
C6 C 0.6081(2) 0.68552(10) 0.19539(7) 0.0267(3) Uani 1 1 d . . . . .
H6 H 0.732905 0.672737 0.178164 0.032 Uiso 1 1 calc R . . . .
C5 C 0.4512(2) 0.70410(11) 0.14309(8) 0.0331(3) Uani 1 1 d . . . . .
H5 H 0.471450 0.704889 0.090632 0.040 Uiso 1 1 calc R . . . .
C12 C 0.7225(2) 0.90225(10) 0.28907(8) 0.0307(3) Uani 1 1 d . . . . .
H12A H 0.813410 0.868493 0.256391 0.046 Uiso 1 1 calc GR . . . .
H12B H 0.732203 0.978676 0.284128 0.046 Uiso 1 1 calc GR . . . .
H12C H 0.590994 0.879780 0.274138 0.046 Uiso 1 1 calc GR . . . .
C14 C 0.7017(2) 0.58693(12) 0.53690(8) 0.0349(3) Uani 1 1 d . . . . .
H14A H 0.591817 0.618279 0.508053 0.052 Uiso 1 1 calc GR . . . .
H14B H 0.719626 0.622218 0.585853 0.052 Uiso 1 1 calc GR . . . .
H14C H 0.676877 0.512111 0.544833 0.052 Uiso 1 1 calc GR . . . .
C3 C 0.2333(2) 0.71900(11) 0.24599(10) 0.0343(3) Uani 1 1 d . . . . .
H3 H 0.107377 0.729510 0.262832 0.041 Uiso 1 1 calc R . . . .
C9 C 0.8072(2) 0.55170(11) 0.33648(8) 0.0295(3) Uani 1 1 d . . . . .
C11 C 0.6060(2) 0.91019(11) 0.42256(9) 0.0363(3) Uani 1 1 d . . . . .
H11A H 0.487637 0.870832 0.409370 0.054 Uiso 1 1 calc GR . . . .
H11B H 0.583710 0.985050 0.412731 0.054 Uiso 1 1 calc GR . . . .
H11C H 0.642777 0.899871 0.476152 0.054 Uiso 1 1 calc GR . . . .
C13 C 0.9665(2) 0.92971(11) 0.39631(8) 0.0354(3) Uani 1 1 d . . . . .
H13A H 1.001964 0.917111 0.449766 0.053 Uiso 1 1 calc GR . . . .
H13B H 0.948487 1.005165 0.387772 0.053 Uiso 1 1 calc GR . . . .
H13C H 1.069406 0.903931 0.365520 0.053 Uiso 1 1 calc GR . . . .
C4 C 0.2640(2) 0.72157(12) 0.16814(9) 0.0372(3) Uani 1 1 d . . . . .
H4 H 0.159486 0.734955 0.132674 0.045 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.5594(10) . ?
S1 O2 1.4293(10) . ?
S1 O1 1.4233(10) . ?
S1 C7 1.8140(12) . ?
F1 C9 1.3346(16) . ?
F3 C9 1.3415(15) . ?
F2 C9 1.3409(17) . ?
O3 C14 1.4542(17) . ?
C8 C1 1.4968(16) . ?
C8 C7 1.3543(17) . ?
C8 C9 1.5294(17) . ?
C1 C2 1.3898(17) . ?
C1 C6 1.3985(16) . ?
C7 C10 1.5584(16) . ?
C10 C12 1.5422(17) . ?
C10 C11 1.5399(18) . ?
C10 C13 1.5500(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.386(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.381(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 H4 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
O3 S1 C7 105.38(5) . . ?
O2 S1 O3 107.62(5) . . ?
O2 S1 C7 107.29(6) . . ?
O1 S1 O3 106.02(6) . . ?
O1 S1 O2 119.30(6) . . ?
O1 S1 C7 110.37(6) . . ?
C14 O3 S1 118.61(9) . . ?
C1 C8 C9 111.04(10) . . ?
C7 C8 C1 122.68(11) . . ?
C7 C8 C9 126.15(11) . . ?
C2 C1 C8 117.12(10) . . ?
C2 C1 C6 119.64(11) . . ?
C6 C1 C8 123.23(11) . . ?
C8 C7 S1 120.87(9) . . ?
C8 C7 C10 126.65(11) . . ?
C10 C7 S1 112.47(8) . . ?
C12 C10 C7 113.05(10) . . ?
C12 C10 C13 104.85(11) . . ?
C11 C10 C7 111.15(10) . . ?
C11 C10 C12 108.16(11) . . ?
C11 C10 C13 110.08(11) . . ?
C13 C10 C7 109.36(11) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.96(12) . . ?
C3 C2 H2 120.0 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.65(13) . . ?
C5 C6 H6 120.2 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.61(13) . . ?
C4 C5 H5 119.7 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.36(14) . . ?
C4 C3 H3 119.8 . . ?
F1 C9 F3 105.53(11) . . ?
F1 C9 F2 108.37(11) . . ?
F1 C9 C8 114.20(11) . . ?
F3 C9 C8 109.95(11) . . ?
F2 C9 F3 106.05(11) . . ?
F2 C9 C8 112.21(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.72(13) . . ?
C3 C4 H4 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.804
_oxdiff_exptl_absorpt_empirical_full_min 0.602
####################################################################### 
# 
# 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_ykd
_database_code_depnum_ccdc_archive 'CCDC 2083913'
loop_
_audit_author_name
_audit_author_address
'xinrui dong'
;State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, School of Pharmacy 
China
;
_audit_update_record             
;
2021-05-15 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_audit_creation_date             2021-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 F4 O2 S'
_chemical_formula_sum            'C13 H14 F4 O2 S'
_chemical_formula_weight         310.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.1315(7)
_cell_length_b                   8.3917(5)
_cell_length_c                   15.5384(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.425(3)
_cell_angle_gamma                90
_cell_volume                     1368.85(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7098
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      68.487
_cell_measurement_theta_min      4.212
_shelx_estimated_absorpt_T_max   0.784
_shelx_estimated_absorpt_T_min   0.749
_exptl_absorpt_coefficient_mu    2.556
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0654 before and 0.0388 after correction.
The Ratio of minimum to maximum transmission is 0.9110.
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    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8209
_diffrn_reflns_point_group_measured_fraction_full 0.733
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.482
_diffrn_reflns_theta_min         4.211
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_source_current           0.64
_diffrn_source_power             0.0286272
_diffrn_source_voltage           44.73
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.472
_reflns_Friedel_fraction_full    0.474
_reflns_Friedel_fraction_max     0.467
_reflns_number_gt                3604
_reflns_number_total             3662
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1114 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         3662
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.071
_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)+(0.0426P)²+0.0171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0625
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 S1, O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C13A(H13A)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C1A(H1AA,H1AB,H1AC),
 C6A(H6AA,H6AB,H6AC), C7A(H7AA,H7AB,H7AC)
;
_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 0.12635(5) 0.47183(7) 0.50060(3) 0.03625(15) Uani 1 1 d . U . . .
F1 F -0.00435(15) 0.5222(2) 0.49991(12) 0.0554(4) Uani 1 1 d . . . . .
F2 F 0.35529(14) 0.32400(18) 0.50394(9) 0.0416(3) Uani 1 1 d . . . . .
F3 F 0.46897(13) 0.1835(2) 0.61471(9) 0.0437(3) Uani 1 1 d . . . . .
F4 F 0.28428(14) 0.09947(17) 0.53494(10) 0.0434(3) Uani 1 1 d . . . . .
O1 O 0.18503(19) 0.6050(2) 0.47361(12) 0.0462(4) Uani 1 1 d . U . . .
O2 O 0.10914(18) 0.3313(2) 0.44619(12) 0.0438(4) Uani 1 1 d . . . . .
C1 C 0.2715(3) 0.5387(3) 0.78246(16) 0.0423(6) Uani 1 1 d . . . . .
H1A H 0.278165 0.437250 0.812220 0.064 Uiso 1 1 calc R U . . .
H1B H 0.250350 0.619118 0.818956 0.064 Uiso 1 1 calc R U . . .
H1C H 0.351459 0.564538 0.774900 0.064 Uiso 1 1 calc R U . . .
C2 C 0.1669(2) 0.5311(3) 0.68845(15) 0.0309(4) Uani 1 1 d . . . . .
C3 C 0.20749(19) 0.4278(2) 0.61949(13) 0.0255(4) Uani 1 1 d . . . . .
C4 C 0.29453(18) 0.3108(2) 0.63890(13) 0.0249(4) Uani 1 1 d . . . . .
C5 C 0.3485(2) 0.2304(3) 0.57136(14) 0.0314(4) Uani 1 1 d . . . . .
C6 C 0.1454(3) 0.7060(3) 0.65643(19) 0.0432(5) Uani 1 1 d . . . . .
H6A H 0.127856 0.769143 0.702386 0.065 Uiso 1 1 calc R U . . .
H6B H 0.074540 0.711965 0.600645 0.065 Uiso 1 1 calc R U . . .
H6C H 0.220513 0.745778 0.646353 0.065 Uiso 1 1 calc R U . . .
C7 C 0.0459(3) 0.4629(4) 0.7016(2) 0.0479(6) Uani 1 1 d . . . . .
H7A H 0.061138 0.354682 0.722463 0.072 Uiso 1 1 calc R U . . .
H7B H -0.022894 0.465806 0.644529 0.072 Uiso 1 1 calc R U . . .
H7C H 0.024089 0.525510 0.745898 0.072 Uiso 1 1 calc R U . . .
C8 C 0.34487(18) 0.2316(2) 0.73032(14) 0.0253(4) Uani 1 1 d . . . . .
C9 C 0.26839(19) 0.1183(3) 0.75245(14) 0.0303(4) Uani 1 1 d . . . . .
H9 H 0.187882 0.095630 0.711511 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3122(2) 0.0396(3) 0.83533(17) 0.0360(5) Uani 1 1 d . . . . .
H10 H 0.261178 -0.036544 0.849666 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4311(2) 0.0734(3) 0.89685(15) 0.0362(5) Uani 1 1 d . . . . .
H11 H 0.459789 0.021028 0.952750 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5080(2) 0.1861(3) 0.87490(15) 0.0330(4) Uani 1 1 d . . . . .
H12 H 0.587757 0.209927 0.916505 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4661(2) 0.2626(3) 0.79148(15) 0.0292(4) Uani 1 1 d . . . . .
H13 H 0.518926 0.334878 0.776136 0.035 Uiso 1 1 calc R U . . .
S1A S 0.84598(5) 0.00332(7) 0.51055(4) 0.03472(14) Uani 1 1 d . . . . .
F1A F 0.72980(15) 0.0426(2) 0.53831(10) 0.0460(4) Uani 1 1 d . . . . .
F2A F 0.78312(14) 0.33037(19) 0.52817(10) 0.0431(3) Uani 1 1 d . . . . .
F3A F 0.6899(2) 0.48009(19) 0.41657(12) 0.0540(4) Uani 1 1 d . . . . .
F4A F 0.58531(15) 0.2914(2) 0.45099(12) 0.0525(4) Uani 1 1 d . . . . .
O1A O 0.95567(18) 0.0697(3) 0.57368(12) 0.0483(4) Uani 1 1 d . . . . .
O2A O 0.83913(17) -0.1663(2) 0.49881(13) 0.0430(4) Uani 1 1 d . . . . .
C1A C 0.8870(2) 0.1073(3) 0.26237(16) 0.0372(5) Uani 1 1 d . . . . .
H1AA H 0.806046 0.130021 0.217080 0.056 Uiso 1 1 calc R U . . .
H1AB H 0.940996 0.055072 0.234136 0.056 Uiso 1 1 calc R U . . .
H1AC H 0.926141 0.205104 0.289866 0.056 Uiso 1 1 calc R U . . .
C2A C 0.8675(2) -0.0018(3) 0.33603(16) 0.0288(4) Uani 1 1 d . . . . .
C3A C 0.80733(18) 0.0909(2) 0.39885(13) 0.0249(4) Uani 1 1 d . . . . .
C4A C 0.73353(19) 0.2214(3) 0.37721(14) 0.0261(4) Uani 1 1 d . . . . .
C5A C 0.6981(2) 0.3293(3) 0.44420(16) 0.0356(5) Uani 1 1 d . . . . .
C6A C 1.0028(2) -0.0600(3) 0.39261(19) 0.0401(5) Uani 1 1 d . . . . .
H6AA H 1.044773 -0.100285 0.352242 0.060 Uiso 1 1 calc R U . . .
H6AB H 0.996477 -0.143104 0.433360 0.060 Uiso 1 1 calc R U . . .
H6AC H 1.050857 0.027276 0.427285 0.060 Uiso 1 1 calc R U . . .
C7A C 0.7857(2) -0.1445(3) 0.29017(18) 0.0411(5) Uani 1 1 d . . . . .
H7AA H 0.702048 -0.108294 0.254676 0.062 Uiso 1 1 calc R U . . .
H7AB H 0.779512 -0.217617 0.336012 0.062 Uiso 1 1 calc R U . . .
H7AC H 0.824177 -0.197062 0.251024 0.062 Uiso 1 1 calc R U . . .
C8A C 0.6674(2) 0.2745(3) 0.28098(15) 0.0277(4) Uani 1 1 d . . . . .
C9A C 0.5633(2) 0.1879(3) 0.22797(15) 0.0323(4) Uani 1 1 d . . . . .
H9A H 0.537220 0.098021 0.252005 0.039 Uiso 1 1 calc R U . . .
C10A C 0.4975(3) 0.2349(4) 0.13888(17) 0.0446(6) Uani 1 1 d . . . . .
H10A H 0.427583 0.176497 0.103405 0.054 Uiso 1 1 calc R U . . .
C11A C 0.5363(3) 0.3686(4) 0.10308(18) 0.0532(7) Uani 1 1 d . . . . .
H11A H 0.493402 0.399082 0.043143 0.064 Uiso 1 1 calc R U . . .
C12A C 0.6386(4) 0.4565(3) 0.1565(2) 0.0515(7) Uani 1 1 d . . . . .
H12A H 0.663419 0.547352 0.132464 0.062 Uiso 1 1 calc R U . . .
C13A C 0.7048(3) 0.4115(3) 0.24518(18) 0.0396(5) Uani 1 1 d . . . . .
H13A H 0.773519 0.471686 0.280752 0.048 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 F1 1.5118(17) . ?
S1 O1 1.426(2) . ?
S1 O2 1.4262(19) . ?
S1 C3 1.804(2) . ?
F2 C5 1.331(3) . ?
F3 C5 1.343(3) . ?
F4 C5 1.331(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.537(3) . ?
C2 C3 1.557(3) . ?
C2 C6 1.543(3) . ?
C2 C7 1.538(3) . ?
C3 C4 1.342(3) . ?
C4 C5 1.529(3) . ?
C4 C8 1.498(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.393(3) . ?
C8 C13 1.392(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
S1A F1A 1.5291(16) . ?
S1A O1A 1.402(2) . ?
S1A O2A 1.4335(19) . ?
S1A C3A 1.800(2) . ?
F2A C5A 1.333(3) . ?
F3A C5A 1.329(3) . ?
F4A C5A 1.333(3) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C1A C2A 1.537(3) . ?
C2A C3A 1.562(3) . ?
C2A C6A 1.549(3) . ?
C2A C7A 1.529(3) . ?
C3A C4A 1.343(3) . ?
C4A C5A 1.527(3) . ?
C4A C8A 1.498(3) . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?
C8A C9A 1.384(3) . ?
C8A C13A 1.399(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.390(3) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.383(5) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.379(5) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.382(4) . ?
C13A H13A 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
F1 S1 C3 102.56(9) . . ?
O1 S1 F1 108.22(12) . . ?
O1 S1 O2 117.24(12) . . ?
O1 S1 C3 109.83(11) . . ?
O2 S1 F1 106.73(11) . . ?
O2 S1 C3 111.14(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 C3 112.06(18) . . ?
C1 C2 C6 104.7(2) . . ?
C1 C2 C7 108.0(2) . . ?
C6 C2 C3 110.91(19) . . ?
C7 C2 C3 110.57(19) . . ?
C7 C2 C6 110.4(2) . . ?
C2 C3 S1 115.45(15) . . ?
C4 C3 S1 117.28(15) . . ?
C4 C3 C2 127.27(19) . . ?
C3 C4 C5 126.01(19) . . ?
C3 C4 C8 123.53(18) . . ?
C8 C4 C5 110.30(17) . . ?
F2 C5 F3 105.04(18) . . ?
F2 C5 C4 114.72(18) . . ?
F3 C5 C4 109.85(17) . . ?
F4 C5 F2 108.39(17) . . ?
F4 C5 F3 106.07(19) . . ?
F4 C5 C4 112.19(18) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C4 118.03(18) . . ?
C13 C8 C4 122.47(19) . . ?
C13 C8 C9 119.45(19) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
F1A S1A C3A 103.34(9) . . ?
O1A S1A F1A 109.78(12) . . ?
O1A S1A O2A 118.71(13) . . ?
O1A S1A C3A 112.67(11) . . ?
O2A S1A F1A 103.63(11) . . ?
O2A S1A C3A 107.27(11) . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
C1A C2A C3A 111.41(17) . . ?
C1A C2A C6A 105.02(19) . . ?
C6A C2A C3A 109.89(19) . . ?
C7A C2A C1A 109.2(2) . . ?
C7A C2A C3A 111.63(18) . . ?
C7A C2A C6A 109.5(2) . . ?
C2A C3A S1A 112.62(15) . . ?
C4A C3A S1A 120.29(16) . . ?
C4A C3A C2A 127.09(19) . . ?
C3A C4A C5A 126.01(19) . . ?
C3A C4A C8A 123.29(18) . . ?
C8A C4A C5A 110.59(17) . . ?
F2A C5A F4A 107.74(19) . . ?
F2A C5A C4A 114.27(18) . . ?
F3A C5A F2A 105.1(2) . . ?
F3A C5A F4A 106.7(2) . . ?
F3A C5A C4A 110.48(19) . . ?
F4A C5A C4A 112.1(2) . . ?
C2A C6A H6AA 109.5 . . ?
C2A C6A H6AB 109.5 . . ?
C2A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C2A C7A H7AA 109.5 . . ?
C2A C7A H7AB 109.5 . . ?
C2A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C9A C8A C4A 118.30(19) . . ?
C9A C8A C13A 119.7(2) . . ?
C13A C8A C4A 121.9(2) . . ?
C8A C9A H9A 119.9 . . ?
C8A C9A C10A 120.2(2) . . ?
C10A C9A H9A 119.9 . . ?
C9A C10A H10A 120.0 . . ?
C11A C10A C9A 119.9(3) . . ?
C11A C10A H10A 120.0 . . ?
C10A C11A H11A 120.1 . . ?
C12A C11A C10A 119.8(2) . . ?
C12A C11A H11A 120.1 . . ?
C11A C12A H12A 119.6 . . ?
C11A C12A C13A 120.9(3) . . ?
C13A C12A H12A 119.6 . . ?
C8A C13A H13A 120.3 . . ?
C12A C13A C8A 119.4(3) . . ?
C12A C13A H13A 120.3 . . ?

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 C3 C4 C5 11.4(3) . . . . ?
S1 C3 C4 C8 -163.57(15) . . . . ?
F1 S1 C3 C2 -32.54(18) . . . . ?
F1 S1 C3 C4 147.07(17) . . . . ?
O1 S1 C3 C2 82.34(18) . . . . ?
O1 S1 C3 C4 -98.04(19) . . . . ?
O2 S1 C3 C2 -146.27(16) . . . . ?
O2 S1 C3 C4 33.3(2) . . . . ?
C1 C2 C3 S1 -156.28(18) . . . . ?
C1 C2 C3 C4 24.1(3) . . . . ?
C2 C3 C4 C5 -169.1(2) . . . . ?
C2 C3 C4 C8 16.0(3) . . . . ?
C3 C4 C5 F2 31.1(3) . . . . ?
C3 C4 C5 F3 149.1(2) . . . . ?
C3 C4 C5 F4 -93.1(3) . . . . ?
C3 C4 C8 C9 77.5(3) . . . . ?
C3 C4 C8 C13 -105.2(2) . . . . ?
C4 C8 C9 C10 178.55(19) . . . . ?
C4 C8 C13 C12 -179.88(19) . . . . ?
C5 C4 C8 C9 -98.2(2) . . . . ?
C5 C4 C8 C13 79.2(2) . . . . ?
C6 C2 C3 S1 -39.7(2) . . . . ?
C6 C2 C3 C4 140.8(2) . . . . ?
C7 C2 C3 S1 83.1(2) . . . . ?
C7 C2 C3 C4 -96.4(3) . . . . ?
C8 C4 C5 F2 -153.38(17) . . . . ?
C8 C4 C5 F3 -35.4(2) . . . . ?
C8 C4 C5 F4 82.4(2) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C8 C13 C12 -2.6(3) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C8 2.4(3) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
S1A C3A C4A C5A 13.7(3) . . . . ?
S1A C3A C4A C8A -162.26(16) . . . . ?
F1A S1A C3A C2A -149.41(15) . . . . ?
F1A S1A C3A C4A 30.3(2) . . . . ?
O1A S1A C3A C2A 92.16(17) . . . . ?
O1A S1A C3A C4A -88.2(2) . . . . ?
O2A S1A C3A C2A -40.31(17) . . . . ?
O2A S1A C3A C4A 139.37(17) . . . . ?
C1A C2A C3A S1A -154.14(16) . . . . ?
C1A C2A C3A C4A 26.2(3) . . . . ?
C2A C3A C4A C5A -166.7(2) . . . . ?
C2A C3A C4A C8A 17.4(3) . . . . ?
C3A C4A C5A F2A 26.9(3) . . . . ?
C3A C4A C5A F3A 145.2(2) . . . . ?
C3A C4A C5A F4A -96.0(3) . . . . ?
C3A C4A C8A C9A 72.8(3) . . . . ?
C3A C4A C8A C13A -109.9(3) . . . . ?
C4A C8A C9A C10A 178.7(2) . . . . ?
C4A C8A C13A C12A -178.7(2) . . . . ?
C5A C4A C8A C9A -103.7(2) . . . . ?
C5A C4A C8A C13A 73.6(2) . . . . ?
C6A C2A C3A S1A -38.2(2) . . . . ?
C6A C2A C3A C4A 142.2(2) . . . . ?
C7A C2A C3A S1A 83.5(2) . . . . ?
C7A C2A C3A C4A -96.2(3) . . . . ?
C8A C4A C5A F2A -156.7(2) . . . . ?
C8A C4A C5A F3A -38.5(3) . . . . ?
C8A C4A C5A F4A 80.4(2) . . . . ?
C8A C9A C10A C11A 0.0(4) . . . . ?
C9A C8A C13A C12A -1.4(4) . . . . ?
C9A C10A C11A C12A -1.2(4) . . . . ?
C10A C11A C12A C13A 1.1(4) . . . . ?
C11A C12A C13A C8A 0.2(4) . . . . ?
C13A C8A C9A C10A 1.3(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_2104122315_0m
_database_code_depnum_ccdc_archive 'CCDC 2083912'
loop_
_audit_author_name
_audit_author_address
'xinrui dong'
;State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, School of Pharmacy 
China
;
_audit_update_record             
;
2021-05-15 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 F3 O3 S Si'
_chemical_formula_sum            'C19 H21 F3 O3 S Si'
_chemical_formula_weight         414.51
_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 0.0148 0.0070 '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 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2153 0.2529 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.4060(3)
_cell_length_b                   15.9894(6)
_cell_length_c                   34.9562(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.362(3)
_cell_angle_gamma                90
_cell_volume                     4127.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      44.428
_cell_measurement_theta_min      3.264
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    1.519
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1557 before and 0.0794 after correction. The Ratio of minimum to maximum transmission is 0.6978. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            46817
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.092
_diffrn_reflns_theta_min         3.263
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4172
_reflns_number_total             7828
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7828
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+6.4085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1955
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C28(H28), C29(H29), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36),
  C37(H37), C38(H38)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C20(H20A,
 H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_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 0.44444(17) 0.95425(7) 0.05563(3) 0.0469(3) Uani 1 1 d . . . . .
Si1 Si 0.23005(19) 0.79499(8) 0.06989(4) 0.0483(4) Uani 1 1 d . . . . .
F1 F 0.5304(4) 1.02997(17) 0.13273(7) 0.0583(7) Uani 1 1 d . . . . .
F2 F 0.3669(4) 1.01340(18) 0.17952(7) 0.0677(9) Uani 1 1 d . . . . .
F3 F 0.2640(4) 1.08348(17) 0.13035(8) 0.0683(8) Uani 1 1 d . . . . .
O1 O 0.4091(4) 1.04971(19) 0.05955(8) 0.0513(8) Uani 1 1 d . . . . .
O2 O 0.6325(4) 0.9426(2) 0.06548(9) 0.0560(9) Uani 1 1 d . . . . .
O3 O 0.3688(5) 0.9270(2) 0.01876(8) 0.0584(9) Uani 1 1 d . . . . .
C1 C 0.2476(8) 1.0854(4) 0.03921(16) 0.0733(17) Uani 1 1 d . . . . .
H1A H 0.260211 1.083595 0.011515 0.110 Uiso 1 1 calc GR . . . .
H1B H 0.233211 1.143561 0.047288 0.110 Uiso 1 1 calc GR . . . .
H1C H 0.140948 1.053008 0.045166 0.110 Uiso 1 1 calc GR . . . .
C2 C 0.3129(6) 0.9030(3) 0.08920(12) 0.0436(11) Uani 1 1 d . . . . .
C3 C 0.1750(8) 0.7214(3) 0.10863(14) 0.0609(14) Uani 1 1 d . . . . .
H3A H 0.274726 0.720683 0.128727 0.091 Uiso 1 1 calc GR . . . .
H3B H 0.157547 0.665030 0.097941 0.091 Uiso 1 1 calc GR . . . .
H3C H 0.063668 0.739655 0.119611 0.091 Uiso 1 1 calc GR . . . .
C4 C 0.4245(8) 0.7458(3) 0.04764(15) 0.0656(15) Uani 1 1 d . . . . .
H4A H 0.453604 0.778411 0.025198 0.098 Uiso 1 1 calc GR . . . .
H4B H 0.392146 0.688580 0.039666 0.098 Uiso 1 1 calc GR . . . .
H4C H 0.529919 0.744346 0.066343 0.098 Uiso 1 1 calc GR . . . .
C5 C 0.0281(7) 0.8098(3) 0.03630(14) 0.0611(14) Uani 1 1 d . . . . .
H5A H -0.074243 0.827449 0.050590 0.092 Uiso 1 1 calc GR . . . .
H5B H -0.001814 0.757071 0.023026 0.092 Uiso 1 1 calc GR . . . .
H5C H 0.052944 0.852873 0.017444 0.092 Uiso 1 1 calc GR . . . .
C6 C 0.2794(6) 0.9363(3) 0.12357(12) 0.0416(11) Uani 1 1 d . . . . .
C7 C 0.3624(7) 1.0160(3) 0.14103(13) 0.0477(12) Uani 1 1 d . . . . .
C8 C 0.1377(6) 0.8981(3) 0.14629(12) 0.0412(11) Uani 1 1 d . . . . .
C9 C 0.1792(6) 0.8599(3) 0.18235(12) 0.0428(11) Uani 1 1 d . . . . .
H9 H 0.299480 0.861455 0.193879 0.051 Uiso 1 1 calc R . . . .
C10 C 0.0464(6) 0.8207(3) 0.20061(12) 0.0417(11) Uani 1 1 d . . . . .
H10 H 0.077249 0.793728 0.224421 0.050 Uiso 1 1 calc R . . . .
C11 C -0.1335(6) 0.8191(3) 0.18542(12) 0.0417(11) Uani 1 1 d . . . . .
C12 C -0.1744(7) 0.8602(3) 0.15051(12) 0.0437(11) Uani 1 1 d . . . . .
H12 H -0.296177 0.861368 0.139775 0.052 Uiso 1 1 calc R . . . .
C13 C -0.0414(6) 0.8989(3) 0.13135(12) 0.0441(11) Uani 1 1 d . . . . .
H13 H -0.072635 0.926515 0.107696 0.053 Uiso 1 1 calc R . . . .
C14 C -0.2744(6) 0.7751(3) 0.20513(13) 0.0423(11) Uani 1 1 d . . . . .
C15 C -0.2789(7) 0.7780(3) 0.24494(13) 0.0472(12) Uani 1 1 d . . . . .
H15 H -0.190175 0.809391 0.259828 0.057 Uiso 1 1 calc R . . . .
C16 C -0.4117(7) 0.7355(3) 0.26293(15) 0.0552(13) Uani 1 1 d . . . . .
H16 H -0.414377 0.738932 0.290010 0.066 Uiso 1 1 calc R . . . .
C17 C -0.5394(7) 0.6887(3) 0.24214(16) 0.0572(14) Uani 1 1 d . . . . .
H17 H -0.629439 0.659307 0.254705 0.069 Uiso 1 1 calc R . . . .
C18 C -0.5358(7) 0.6847(3) 0.20320(16) 0.0564(13) Uani 1 1 d . . . . .
H18 H -0.623225 0.651768 0.188710 0.068 Uiso 1 1 calc R . . . .
C19 C -0.4064(7) 0.7280(3) 0.18454(14) 0.0486(12) Uani 1 1 d . . . . .
H19 H -0.407775 0.725527 0.157367 0.058 Uiso 1 1 calc R . . . .
S2 S 0.94114(19) 0.29823(8) 0.07284(4) 0.0572(4) Uani 1 1 d . . . . .
Si2 Si 0.7259(2) 0.45971(9) 0.08167(4) 0.0597(4) Uani 1 1 d . . . . .
F4 F 1.0363(4) 0.23856(18) 0.15254(8) 0.0673(8) Uani 1 1 d . . . . .
F5 F 0.8745(4) 0.26330(18) 0.19905(8) 0.0697(9) Uani 1 1 d . . . . .
F6 F 0.7706(4) 0.18378(17) 0.15354(8) 0.0682(8) Uani 1 1 d . . . . .
O4 O 0.9126(5) 0.2031(2) 0.08117(10) 0.0608(9) Uani 1 1 d . . . . .
O5 O 0.8593(5) 0.3168(2) 0.03555(9) 0.0718(11) Uani 1 1 d . . . . .
O6 O 1.1286(5) 0.3131(2) 0.08086(11) 0.0735(11) Uani 1 1 d . . . . .
C20 C 0.7414(8) 0.1644(4) 0.06736(16) 0.0783(18) Uani 1 1 d . . . . .
H20A H 0.723904 0.170443 0.039426 0.117 Uiso 1 1 calc GR . . . .
H20B H 0.641585 0.191826 0.079304 0.117 Uiso 1 1 calc GR . . . .
H20C H 0.743799 0.104861 0.074074 0.117 Uiso 1 1 calc GR . . . .
C21 C 0.8102(7) 0.3556(3) 0.10494(13) 0.0476(12) Uani 1 1 d . . . . .
C22 C 0.6802(8) 0.5396(3) 0.11829(15) 0.0688(16) Uani 1 1 d . . . . .
H22A H 0.566797 0.525961 0.129642 0.103 Uiso 1 1 calc GR . . . .
H22B H 0.669750 0.594771 0.106157 0.103 Uiso 1 1 calc GR . . . .
H22C H 0.779858 0.540068 0.138407 0.103 Uiso 1 1 calc GR . . . .
C23 C 0.5192(9) 0.4401(4) 0.04955(16) 0.088(2) Uani 1 1 d . . . . .
H23A H 0.546467 0.399394 0.029831 0.132 Uiso 1 1 calc GR . . . .
H23B H 0.478410 0.492575 0.037254 0.132 Uiso 1 1 calc GR . . . .
H23C H 0.423545 0.417945 0.064587 0.132 Uiso 1 1 calc GR . . . .
C24 C 0.9141(10) 0.5032(4) 0.05547(18) 0.096(2) Uani 1 1 d . . . . .
H24A H 1.024014 0.506638 0.072873 0.144 Uiso 1 1 calc GR . . . .
H24B H 0.881231 0.559232 0.045928 0.144 Uiso 1 1 calc GR . . . .
H24C H 0.936217 0.466695 0.033800 0.144 Uiso 1 1 calc GR . . . .
C25 C 0.7798(6) 0.3284(3) 0.14066(12) 0.0434(11) Uani 1 1 d . . . . .
C26 C 0.8647(8) 0.2534(3) 0.16077(14) 0.0536(13) Uani 1 1 d . . . . .
C27 C 0.6405(6) 0.3705(3) 0.16198(12) 0.0389(10) Uani 1 1 d . . . . .
C28 C 0.6838(6) 0.4128(3) 0.19685(12) 0.0424(11) Uani 1 1 d . . . . .
H28 H 0.805440 0.413924 0.207621 0.051 Uiso 1 1 calc R . . . .
C29 C 0.5502(6) 0.4526(3) 0.21539(12) 0.0426(11) Uani 1 1 d . . . . .
H29 H 0.581927 0.481116 0.238776 0.051 Uiso 1 1 calc R . . . .
C30 C 0.3703(6) 0.4520(3) 0.20075(12) 0.0414(11) Uani 1 1 d . . . . .
C31 C 0.3284(7) 0.4090(3) 0.16662(13) 0.0480(12) Uani 1 1 d . . . . .
H31 H 0.206487 0.407609 0.155973 0.058 Uiso 1 1 calc R . . . .
C32 C 0.4602(7) 0.3683(3) 0.14797(13) 0.0478(12) Uani 1 1 d . . . . .
H32 H 0.426999 0.338107 0.125096 0.057 Uiso 1 1 calc R . . . .
C33 C 0.2292(6) 0.4955(3) 0.22099(14) 0.0434(11) Uani 1 1 d . . . . .
C34 C 0.0923(7) 0.5407(3) 0.20118(16) 0.0539(13) Uani 1 1 d . . . . .
H34 H 0.087119 0.543231 0.173969 0.065 Uiso 1 1 calc R . . . .
C35 C -0.0371(8) 0.5824(3) 0.22067(18) 0.0632(15) Uani 1 1 d . . . . .
H35 H -0.129442 0.613780 0.206816 0.076 Uiso 1 1 calc R . . . .
C36 C -0.0317(8) 0.5783(3) 0.2601(2) 0.0678(16) Uani 1 1 d . . . . .
H36 H -0.121112 0.606344 0.273378 0.081 Uiso 1 1 calc R . . . .
C37 C 0.1014(8) 0.5343(3) 0.28002(16) 0.0596(14) Uani 1 1 d . . . . .
H37 H 0.104853 0.531901 0.307218 0.072 Uiso 1 1 calc R . . . .
C38 C 0.2319(7) 0.4929(3) 0.26094(14) 0.0495(12) Uani 1 1 d . . . . .
H38 H 0.324375 0.462458 0.275183 0.059 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.556(3) . ?
S1 O2 1.421(3) . ?
S1 O3 1.434(3) . ?
S1 C2 1.781(5) . ?
Si1 C2 1.937(5) . ?
Si1 C3 1.863(5) . ?
Si1 C4 1.862(5) . ?
Si1 C5 1.845(5) . ?
F1 C7 1.318(5) . ?
F2 C7 1.344(5) . ?
F3 C7 1.339(5) . ?
O1 C1 1.460(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C6 1.354(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.522(6) . ?
C6 C8 1.494(6) . ?
C8 C9 1.413(6) . ?
C8 C13 1.388(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.364(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(6) . ?
C11 C12 1.398(6) . ?
C11 C14 1.473(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(6) . ?
C14 C19 1.390(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.371(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.365(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(7) . ?
C19 H19 0.9500 . ?
S2 O4 1.566(4) . ?
S2 O5 1.426(4) . ?
S2 O6 1.416(4) . ?
S2 C21 1.790(5) . ?
Si2 C21 1.936(5) . ?
Si2 C22 1.857(5) . ?
Si2 C23 1.855(6) . ?
Si2 C24 1.860(6) . ?
F4 C26 1.345(6) . ?
F5 C26 1.344(5) . ?
F6 C26 1.327(6) . ?
O4 C20 1.460(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C25 1.357(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.504(7) . ?
C25 C27 1.479(6) . ?
C27 C28 1.410(6) . ?
C27 C32 1.388(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.378(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.391(6) . ?
C30 C31 1.392(6) . ?
C30 C33 1.479(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.378(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.387(6) . ?
C33 C38 1.395(6) . ?
C34 H34 0.9500 . ?
C34 C35 1.388(7) . ?
C35 H35 0.9500 . ?
C35 C36 1.377(8) . ?
C36 H36 0.9500 . ?
C36 C37 1.360(8) . ?
C37 H37 0.9500 . ?
C37 C38 1.383(7) . ?
C38 H38 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 C2 106.79(19) . . ?
O2 S1 O1 106.0(2) . . ?
O2 S1 O3 119.1(2) . . ?
O2 S1 C2 110.8(2) . . ?
O3 S1 O1 108.69(19) . . ?
O3 S1 C2 104.9(2) . . ?
C3 Si1 C2 113.0(2) . . ?
C4 Si1 C2 106.7(2) . . ?
C4 Si1 C3 104.8(2) . . ?
C5 Si1 C2 109.1(2) . . ?
C5 Si1 C3 109.4(3) . . ?
C5 Si1 C4 113.8(2) . . ?
C1 O1 S1 118.5(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S1 C2 Si1 110.8(2) . . ?
C6 C2 S1 123.4(4) . . ?
C6 C2 Si1 125.8(3) . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si1 C4 H4A 109.5 . . ?
Si1 C4 H4B 109.5 . . ?
Si1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 C7 126.1(4) . . ?
C2 C6 C8 119.6(4) . . ?
C8 C6 C7 114.1(4) . . ?
F1 C7 F2 105.9(4) . . ?
F1 C7 F3 107.8(4) . . ?
F1 C7 C6 114.4(4) . . ?
F2 C7 C6 110.7(4) . . ?
F3 C7 F2 106.0(4) . . ?
F3 C7 C6 111.6(4) . . ?
C9 C8 C6 122.5(4) . . ?
C13 C8 C6 119.0(4) . . ?
C13 C8 C9 118.5(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 122.1(4) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 117.5(4) . . ?
C10 C11 C14 121.3(4) . . ?
C12 C11 C14 121.2(4) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.7(4) . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C11 121.5(4) . . ?
C19 C14 C11 120.8(4) . . ?
C19 C14 C15 117.7(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(5) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.3(5) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.8(5) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(5) . . ?
C18 C19 H19 119.6 . . ?
O4 S2 C21 107.1(2) . . ?
O5 S2 O4 108.5(2) . . ?
O5 S2 C21 104.7(2) . . ?
O6 S2 O4 105.7(2) . . ?
O6 S2 O5 119.2(2) . . ?
O6 S2 C21 111.1(2) . . ?
C22 Si2 C21 111.8(2) . . ?
C22 Si2 C24 105.4(3) . . ?
C23 Si2 C21 109.5(2) . . ?
C23 Si2 C22 110.4(3) . . ?
C23 Si2 C24 112.3(3) . . ?
C24 Si2 C21 107.4(3) . . ?
C20 O4 S2 118.5(4) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S2 C21 Si2 110.5(2) . . ?
C25 C21 S2 123.3(4) . . ?
C25 C21 Si2 126.2(4) . . ?
Si2 C22 H22A 109.5 . . ?
Si2 C22 H22B 109.5 . . ?
Si2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si2 C23 H23A 109.5 . . ?
Si2 C23 H23B 109.5 . . ?
Si2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Si2 C24 H24A 109.5 . . ?
Si2 C24 H24B 109.5 . . ?
Si2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 C26 126.4(4) . . ?
C21 C25 C27 119.3(4) . . ?
C27 C25 C26 114.2(4) . . ?
F4 C26 F5 104.7(4) . . ?
F4 C26 C25 114.1(4) . . ?
F5 C26 C25 111.1(4) . . ?
F6 C26 F4 107.6(4) . . ?
F6 C26 F5 106.0(4) . . ?
F6 C26 C25 112.6(4) . . ?
C28 C27 C25 122.2(4) . . ?
C32 C27 C25 120.0(4) . . ?
C32 C27 C28 117.8(4) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.3(4) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.1 . . ?
C28 C29 C30 121.7(4) . . ?
C30 C29 H29 119.1 . . ?
C29 C30 C31 117.6(4) . . ?
C29 C30 C33 120.9(4) . . ?
C31 C30 C33 121.5(4) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 C30 121.3(5) . . ?
C32 C31 H31 119.4 . . ?
C27 C32 H32 119.4 . . ?
C31 C32 C27 121.3(4) . . ?
C31 C32 H32 119.4 . . ?
C34 C33 C30 121.5(4) . . ?
C34 C33 C38 118.0(5) . . ?
C38 C33 C30 120.5(4) . . ?
C33 C34 H34 119.6 . . ?
C33 C34 C35 120.8(5) . . ?
C35 C34 H34 119.6 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 119.9(5) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.9 . . ?
C37 C36 C35 120.2(5) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.4(5) . . ?
C38 C37 H37 119.8 . . ?
C33 C38 H38 119.6 . . ?
C37 C38 C33 120.7(5) . . ?
C37 C38 H38 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
