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

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

data_exp_12593_auto
_database_code_depnum_ccdc_archive 'CCDC 2192274'
loop_
_audit_author_name
_audit_author_address
'Chang-Lun Shao'
;Ocean University of China
China
;
_audit_update_record             
;
2022-07-24 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H34 N2 O5'
_chemical_formula_weight         490.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.18453(19)
_cell_length_b                   14.1629(3)
_cell_length_c                   23.0774(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2675.06(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3365
_cell_measurement_theta_min      4.9380
_cell_measurement_theta_max      70.5870

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.672
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_T_min  0.84560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6226
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.662
_diffrn_reflns_theta_max         67.169
_diffrn_reflns_theta_full        67.169
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.857
_reflns_number_total             4110
_reflns_number_gt                3372
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.506
_reflns_Friedel_fraction_max     0.671
_reflns_Friedel_fraction_full    0.671

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0666P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(14)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         4110
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N2 N 0.0046(8) 0.5113(8) 0.8077(3) 0.201(4) Uani 1 1 d . . . . .
O1 O 0.6234(3) 0.35121(15) 0.08737(11) 0.0458(6) Uani 1 1 d . . . . .
O2 O 0.4223(2) 0.49279(16) 0.07183(10) 0.0447(5) Uani 1 1 d . . . . .
H2 H 0.434124 0.435315 0.072783 0.067 Uiso 1 1 calc R U . . .
O3 O 0.5422(3) 0.65842(17) 0.11326(9) 0.0507(6) Uani 1 1 d . . . . .
O4 O 0.6603(3) 0.76737(15) -0.00171(11) 0.0502(6) Uani 1 1 d . . . . .
O5 O 0.4607(4) 0.4931(2) -0.20064(10) 0.0664(7) Uani 1 1 d . . . . .
N1 N 0.8281(3) 0.65571(18) 0.03490(12) 0.0416(6) Uani 1 1 d . . . . .
H1 H 0.912828 0.688245 0.025581 0.050 Uiso 1 1 calc R U . . .
C1 C 0.4946(5) 0.4994(2) -0.14283(14) 0.0493(8) Uani 1 1 d . . . . .
C2 C 0.3645(5) 0.5254(2) -0.10779(15) 0.0519(9) Uani 1 1 d . . . . .
H2A H 0.262403 0.536511 -0.124101 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3861(4) 0.5346(2) -0.04916(15) 0.0446(8) Uani 1 1 d . . . . .
H3 H 0.297856 0.552079 -0.026148 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5380(4) 0.51829(19) -0.02318(13) 0.0364(7) Uani 1 1 d . . . . .
C5 C 0.6656(4) 0.4914(2) -0.05893(14) 0.0488(8) Uani 1 1 d . . . . .
H5 H 0.767480 0.478977 -0.042801 0.059 Uiso 1 1 calc R U . . .
C6 C 0.6444(5) 0.4825(3) -0.11854(15) 0.0558(9) Uani 1 1 d . . . . .
H6 H 0.732024 0.465138 -0.141872 0.067 Uiso 1 1 calc R U . . .
C7 C 0.5563(4) 0.5345(2) 0.04178(13) 0.0340(7) Uani 1 1 d . . . . .
C8 C 0.5393(4) 0.6406(2) 0.05300(13) 0.0366(7) Uani 1 1 d . . . . .
H8 H 0.435627 0.663052 0.036805 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6798(4) 0.6939(2) 0.02500(14) 0.0389(7) Uani 1 1 d . . . . .
C10 C 0.8530(4) 0.5654(2) 0.05967(13) 0.0370(7) Uani 1 1 d . . . . .
C11 C 1.0096(4) 0.5392(2) 0.07528(14) 0.0433(8) Uani 1 1 d . . . . .
H11 H 1.096183 0.581164 0.071249 0.052 Uiso 1 1 calc R U . . .
C12 C 1.0354(4) 0.4489(2) 0.09711(14) 0.0454(8) Uani 1 1 d . . . . .
H12 H 1.140540 0.431528 0.108053 0.054 Uiso 1 1 calc R U . . .
C13 C 0.9113(4) 0.3844(2) 0.10311(13) 0.0371(7) Uani 1 1 d . . . . .
C14 C 0.9425(4) 0.2854(2) 0.12746(14) 0.0435(8) Uani 1 1 d . . . . .
H14 H 0.993897 0.248102 0.096693 0.052 Uiso 1 1 calc R U . . .
C15 C 1.0579(5) 0.2865(2) 0.17811(16) 0.0533(9) Uani 1 1 d . . . . .
H15 H 1.167068 0.299759 0.170479 0.064 Uiso 1 1 calc R U . . .
C16 C 1.0168(6) 0.2701(2) 0.23282(17) 0.0597(11) Uani 1 1 d . . . . .
C17 C 0.8439(6) 0.2511(3) 0.24925(17) 0.0671(11) Uani 1 1 d . . . . .
H17A H 0.817183 0.288319 0.283257 0.081 Uiso 1 1 calc R U . . .
H17B H 0.833248 0.185058 0.259646 0.081 Uiso 1 1 calc R U . . .
C18 C 0.7214(5) 0.2737(3) 0.20158(15) 0.0541(9) Uani 1 1 d . . . . .
H18A H 0.705642 0.341501 0.199401 0.065 Uiso 1 1 calc R U . . .
H18B H 0.617002 0.244990 0.210837 0.065 Uiso 1 1 calc R U . . .
C19 C 0.7807(4) 0.2371(2) 0.14302(14) 0.0434(8) Uani 1 1 d . . . . .
H19 H 0.801923 0.169283 0.146977 0.052 Uiso 1 1 calc R U . . .
C20 C 0.6582(4) 0.2505(2) 0.09356(15) 0.0468(8) Uani 1 1 d . . . . .
C21 C 0.7548(4) 0.4118(2) 0.08533(13) 0.0357(7) Uani 1 1 d . . . . .
C22 C 0.7231(3) 0.5024(2) 0.06431(12) 0.0348(6) Uani 1 1 d . . . . .
C23 C 0.5950(6) 0.4791(3) -0.23877(17) 0.0720(12) Uani 1 1 d . . . . .
H23A H 0.674719 0.527834 -0.232632 0.108 Uiso 1 1 calc R U . . .
H23B H 0.557462 0.481376 -0.278154 0.108 Uiso 1 1 calc R U . . .
H23C H 0.643639 0.418635 -0.231273 0.108 Uiso 1 1 calc R U . . .
C24 C 0.4836(7) 0.7497(3) 0.1275(2) 0.0830(15) Uani 1 1 d . . . . .
H24A H 0.545408 0.796369 0.106735 0.124 Uiso 1 1 calc R U . . .
H24B H 0.495347 0.760097 0.168410 0.124 Uiso 1 1 calc R U . . .
H24C H 0.370420 0.754599 0.117027 0.124 Uiso 1 1 calc R U . . .
C25 C 1.1416(8) 0.2701(3) 0.2813(2) 0.0878(16) Uani 1 1 d . . . . .
H25A H 1.249532 0.273331 0.265075 0.132 Uiso 1 1 calc R U . . .
H25B H 1.130839 0.213151 0.303527 0.132 Uiso 1 1 calc R U . . .
H25C H 1.123635 0.323695 0.305887 0.132 Uiso 1 1 calc R U . . .
C26 C 0.4925(5) 0.2066(3) 0.1062(2) 0.0723(13) Uani 1 1 d . . . . .
H26A H 0.451243 0.230918 0.142152 0.108 Uiso 1 1 calc R U . . .
H26B H 0.503693 0.139285 0.108895 0.108 Uiso 1 1 calc R U . . .
H26C H 0.417955 0.221946 0.075482 0.108 Uiso 1 1 calc R U . . .
C27 C 0.7209(6) 0.2142(3) 0.03555(17) 0.0701(12) Uani 1 1 d . . . . .
H27A H 0.639966 0.225190 0.006199 0.105 Uiso 1 1 calc R U . . .
H27B H 0.742570 0.147781 0.038348 0.105 Uiso 1 1 calc R U . . .
H27C H 0.819700 0.246921 0.025525 0.105 Uiso 1 1 calc R U . . .
C28 C 0.1200(10) 0.5015(5) 0.7085(2) 0.134(3) Uani 1 1 d . . . . .
H28A H 0.123401 0.564076 0.692544 0.201 Uiso 1 1 calc R U . . .
H28B H 0.054776 0.461657 0.684095 0.201 Uiso 1 1 calc R U . . .
H28C H 0.228904 0.476645 0.710858 0.201 Uiso 1 1 calc R U . . .
C29 C 0.0539(7) 0.5046(6) 0.7620(3) 0.109(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C29 1.133(8) . ?
O1 C21 1.377(4) . ?
O1 C20 1.462(4) . ?
O2 C7 1.426(3) . ?
O3 C8 1.414(4) . ?
O3 C24 1.418(5) . ?
O4 C9 1.220(4) . ?
O5 C1 1.366(4) . ?
O5 C23 1.422(5) . ?
N1 C9 1.348(4) . ?
N1 C10 1.416(4) . ?
C1 C6 1.369(5) . ?
C1 C2 1.387(5) . ?
C2 C3 1.371(5) . ?
C3 C4 1.400(4) . ?
C4 C5 1.384(4) . ?
C4 C7 1.524(4) . ?
C5 C6 1.392(5) . ?
C7 C22 1.530(4) . ?
C7 C8 1.532(4) . ?
C8 C9 1.519(4) . ?
C10 C11 1.382(4) . ?
C10 C22 1.392(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.373(4) . ?
C13 C21 1.400(4) . ?
C13 C14 1.531(4) . ?
C14 C15 1.503(5) . ?
C14 C19 1.533(5) . ?
C15 C16 1.327(5) . ?
C16 C17 1.490(7) . ?
C16 C25 1.514(6) . ?
C17 C18 1.523(5) . ?
C18 C19 1.527(5) . ?
C19 C20 1.531(5) . ?
C20 C26 1.520(5) . ?
C20 C27 1.523(5) . ?
C21 C22 1.396(4) . ?
C28 C29 1.348(8) . ?

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
C21 O1 C20 117.4(2) . . ?
C8 O3 C24 112.6(3) . . ?
C1 O5 C23 117.2(3) . . ?
C9 N1 C10 124.1(3) . . ?
O5 C1 C6 124.8(3) . . ?
O5 C1 C2 115.5(3) . . ?
C6 C1 C2 119.7(3) . . ?
C3 C2 C1 120.1(3) . . ?
C2 C3 C4 121.4(3) . . ?
C5 C4 C3 117.4(3) . . ?
C5 C4 C7 123.6(3) . . ?
C3 C4 C7 118.9(3) . . ?
C4 C5 C6 121.3(3) . . ?
C1 C6 C5 120.0(4) . . ?
O2 C7 C4 109.9(2) . . ?
O2 C7 C22 113.5(2) . . ?
C4 C7 C22 112.2(2) . . ?
O2 C7 C8 104.7(2) . . ?
C4 C7 C8 107.8(2) . . ?
C22 C7 C8 108.4(3) . . ?
O3 C8 C9 108.5(3) . . ?
O3 C8 C7 109.8(2) . . ?
C9 C8 C7 110.3(3) . . ?
O4 C9 N1 123.0(3) . . ?
O4 C9 C8 122.7(3) . . ?
N1 C9 C8 114.2(3) . . ?
C11 C10 C22 121.1(3) . . ?
C11 C10 N1 118.8(3) . . ?
C22 C10 N1 120.0(3) . . ?
C10 C11 C12 118.9(3) . . ?
C13 C12 C11 122.4(3) . . ?
C12 C13 C21 117.5(3) . . ?
C12 C13 C14 121.5(3) . . ?
C21 C13 C14 121.0(3) . . ?
C15 C14 C13 112.4(3) . . ?
C15 C14 C19 111.4(3) . . ?
C13 C14 C19 110.5(3) . . ?
C16 C15 C14 125.4(4) . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 C25 122.1(5) . . ?
C17 C16 C25 116.9(4) . . ?
C16 C17 C18 113.8(3) . . ?
C17 C18 C19 111.0(3) . . ?
C18 C19 C20 114.2(3) . . ?
C18 C19 C14 109.3(3) . . ?
C20 C19 C14 109.6(3) . . ?
O1 C20 C26 104.1(3) . . ?
O1 C20 C27 108.0(3) . . ?
C26 C20 C27 109.4(3) . . ?
O1 C20 C19 108.7(3) . . ?
C26 C20 C19 113.0(3) . . ?
C27 C20 C19 113.1(3) . . ?
O1 C21 C22 116.1(3) . . ?
O1 C21 C13 122.1(3) . . ?
C22 C21 C13 121.8(3) . . ?
C10 C22 C21 118.3(3) . . ?
C10 C22 C7 117.7(3) . . ?
C21 C22 C7 123.9(3) . . ?
N2 C29 C28 175.9(9) . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_12879
_database_code_depnum_ccdc_archive 'CCDC 2203050'
loop_
_audit_author_name
_audit_author_address
'Chang-Lun Shao'
;Ocean University of China
China
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H27 F3 O4 S Si'
_chemical_formula_weight         448.56

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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.3049(5)
_cell_length_b                   13.3957(7)
_cell_length_c                   16.3644(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2259.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1992
_cell_measurement_theta_min      4.2560
_cell_measurement_theta_max      70.0090

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.207
_shelx_estimated_absorpt_T_min   0.778
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_T_min  0.67768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5581
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.265
_diffrn_reflns_theta_max         67.226
_diffrn_reflns_theta_full        67.226
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_point_group_measured_fraction_full 0.872
_reflns_number_total             3523
_reflns_number_gt                2833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.540
_reflns_Friedel_fraction_max     0.711
_reflns_Friedel_fraction_full    0.711

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.3077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(17)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         3523
_refine_ls_number_parameters     333
_refine_ls_number_restraints     643
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Si1 Si 0.51964(14) -0.08798(10) 0.95489(8) 0.0579(4) Uani 1 1 d . . . . .
S1 S 0.8538(3) -0.1437(2) 0.8580(2) 0.0651(8) Uani 0.649(6) 1 d D U P A 1
F1 F 0.9966(7) 0.0016(6) 0.8050(8) 0.142(3) Uani 0.649(6) 1 d D U P A 1
F2 F 1.0939(7) -0.1408(8) 0.8166(8) 0.138(3) Uani 0.649(6) 1 d D U P A 1
F3 F 0.9584(13) -0.1334(8) 0.7123(6) 0.135(4) Uani 0.649(6) 1 d D U P A 1
O1 O 0.8630(9) -0.0948(7) 0.9325(5) 0.098(3) Uani 0.649(6) 1 d D U P A 1
O2 O 0.8610(7) -0.2471(4) 0.8487(6) 0.100(2) Uani 0.649(6) 1 d D U P A 1
C17 C 0.9847(10) -0.0970(8) 0.7902(7) 0.096(3) Uani 0.649(6) 1 d D U P A 1
S1' S 0.8939(8) -0.1042(6) 0.8582(4) 0.082(2) Uani 0.351(6) 1 d D U P A 2
O1' O 0.9577(18) -0.0136(13) 0.8735(13) 0.114(5) Uani 0.351(6) 1 d . U P A 2
O2' O 0.893(2) -0.1626(16) 0.9281(10) 0.130(5) Uani 0.351(6) 1 d D U P A 2
F2' F 0.9097(15) -0.2535(11) 0.7651(11) 0.151(5) Uani 0.351(6) 1 d D U P A 2
F1' F 0.981(2) -0.0856(13) 0.7274(12) 0.115(5) Uani 0.351(6) 1 d D U P A 2
C17' C 0.9769(15) -0.1664(11) 0.7801(9) 0.096(4) Uani 0.351(6) 1 d D U P A 2
F3' F 1.0943(17) -0.1978(13) 0.8097(14) 0.139(5) Uani 0.351(6) 1 d D U P A 2
O3 O 0.7402(3) -0.1053(3) 0.8128(2) 0.0704(10) Uani 1 1 d D U . . .
O4 O 0.4594(3) 0.1233(2) 0.9476(2) 0.0618(9) Uani 1 1 d . . . . .
C1 C 0.5910(4) 0.0079(3) 0.8814(3) 0.0477(10) Uani 1 1 d . . . . .
C2 C 0.6812(5) -0.0076(4) 0.8207(3) 0.0532(11) Uani 1 1 d . . . . .
C3 C 0.7175(5) 0.0606(4) 0.7626(3) 0.0591(13) Uani 1 1 d . . . . .
H3 H 0.776731 0.044346 0.721830 0.071 Uiso 1 1 calc R U . . .
C4 C 0.6622(5) 0.1548(4) 0.7672(3) 0.0552(12) Uani 1 1 d . . . . .
H4 H 0.684780 0.202252 0.728257 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5749(4) 0.1804(3) 0.8275(3) 0.0455(10) Uani 1 1 d . . . . .
C6 C 0.5129(4) 0.2824(3) 0.8325(3) 0.0487(10) Uani 1 1 d . . . . .
H6 H 0.435733 0.281256 0.797514 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5960(5) 0.3670(4) 0.8043(3) 0.0581(12) Uani 1 1 d . . . . .
H7 H 0.652255 0.355822 0.760802 0.070 Uiso 1 1 calc R U . . .
C8 C 0.5940(5) 0.4576(4) 0.8378(3) 0.0602(13) Uani 1 1 d . . . . .
C9 C 0.5073(6) 0.4843(4) 0.9068(4) 0.0735(16) Uani 1 1 d . . . . .
H9A H 0.463537 0.546515 0.894125 0.088 Uiso 1 1 calc R U . . .
H9B H 0.559658 0.495243 0.955304 0.088 Uiso 1 1 calc R U . . .
C10 C 0.4066(5) 0.4053(4) 0.9252(3) 0.0645(13) Uani 1 1 d . . . . .
H10A H 0.335782 0.410571 0.886403 0.077 Uiso 1 1 calc R U . . .
H10B H 0.371581 0.415927 0.979582 0.077 Uiso 1 1 calc R U . . .
C11 C 0.4668(5) 0.3006(3) 0.9201(3) 0.0504(11) Uani 1 1 d . . . . .
H11 H 0.544920 0.302085 0.954217 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3844(4) 0.2158(4) 0.9518(3) 0.0538(11) Uani 1 1 d . . . . .
C13 C 0.5420(4) 0.1064(3) 0.8835(3) 0.0462(10) Uani 1 1 d . . . . .
C14 C 0.3387(6) -0.0800(5) 0.9509(5) 0.095(2) Uani 1 1 d . . . . .
H14A H 0.301910 -0.140921 0.971282 0.142 Uiso 1 1 calc R U . . .
H14B H 0.311460 -0.069879 0.895393 0.142 Uiso 1 1 calc R U . . .
H14C H 0.309847 -0.025071 0.983885 0.142 Uiso 1 1 calc R U . . .
C15 C 0.5815(7) -0.0627(5) 1.0584(3) 0.091(2) Uani 1 1 d . . . . .
H15A H 0.534352 -0.102154 1.097324 0.137 Uiso 1 1 calc R U . . .
H15B H 0.570552 0.006831 1.070893 0.137 Uiso 1 1 calc R U . . .
H15C H 0.672001 -0.079532 1.060978 0.137 Uiso 1 1 calc R U . . .
C16 C 0.5568(8) -0.2187(4) 0.9236(4) 0.093(2) Uani 1 1 d . . . . .
H16A H 0.646736 -0.232663 0.933721 0.140 Uiso 1 1 calc R U . . .
H16B H 0.538688 -0.226810 0.866453 0.140 Uiso 1 1 calc R U . . .
H16C H 0.503994 -0.264094 0.954592 0.140 Uiso 1 1 calc R U . . .
C18 C 0.6815(7) 0.5395(4) 0.8082(4) 0.0841(18) Uani 1 1 d . . . . .
H18A H 0.739872 0.558487 0.851190 0.126 Uiso 1 1 calc R U . . .
H18B H 0.630211 0.596065 0.792348 0.126 Uiso 1 1 calc R U . . .
H18C H 0.730537 0.516264 0.762039 0.126 Uiso 1 1 calc R U . . .
C19 C 0.2594(5) 0.1995(5) 0.9038(4) 0.0785(17) Uani 1 1 d . . . . .
H19A H 0.280222 0.181212 0.848566 0.118 Uiso 1 1 calc R U . . .
H19B H 0.209479 0.260010 0.903630 0.118 Uiso 1 1 calc R U . . .
H19C H 0.209945 0.147097 0.928809 0.118 Uiso 1 1 calc R U . . .
C20 C 0.3568(6) 0.2255(5) 1.0427(3) 0.0743(16) Uani 1 1 d . . . . .
H20A H 0.314691 0.166000 1.061849 0.111 Uiso 1 1 calc R U . . .
H20B H 0.301316 0.281948 1.051966 0.111 Uiso 1 1 calc R U . . .
H20C H 0.436898 0.234653 1.071688 0.111 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
Si1 C15 1.842(6) . ?
Si1 C16 1.865(6) . ?
Si1 C14 1.869(6) . ?
Si1 C1 1.908(5) . ?
S1 O1 1.387(7) . ?
S1 O2 1.396(6) . ?
S1 O3 1.477(5) . ?
S1 C17 1.855(13) . ?
F1 C17 1.349(10) . ?
F2 C17 1.341(9) . ?
F3 C17 1.391(10) . ?
S1' O2' 1.386(9) . ?
S1' O1' 1.40(2) . ?
S1' C17' 1.748(12) . ?
S1' O3 1.749(8) . ?
F2' C17' 1.378(11) . ?
F1' C17' 1.385(12) . ?
C17' F3' 1.370(12) . ?
O3 C2 1.450(5) . ?
O4 C13 1.369(5) . ?
O4 C12 1.463(5) . ?
C1 C2 1.375(6) . ?
C1 C13 1.413(6) . ?
C2 C3 1.371(7) . ?
C3 C4 1.386(7) . ?
C4 C5 1.380(6) . ?
C5 C13 1.392(6) . ?
C5 C6 1.510(6) . ?
C6 C7 1.493(7) . ?
C6 C11 1.530(6) . ?
C7 C8 1.331(7) . ?
C8 C9 1.484(8) . ?
C8 C18 1.501(8) . ?
C9 C10 1.513(8) . ?
C10 C11 1.536(6) . ?
C11 C12 1.509(7) . ?
C12 C20 1.520(6) . ?
C12 C19 1.525(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 Si1 C16 110.7(3) . . ?
C15 Si1 C14 111.6(4) . . ?
C16 Si1 C14 104.4(3) . . ?
C15 Si1 C1 108.8(2) . . ?
C16 Si1 C1 112.4(3) . . ?
C14 Si1 C1 108.9(3) . . ?
O1 S1 O2 124.1(6) . . ?
O1 S1 O3 109.3(4) . . ?
O2 S1 O3 109.4(4) . . ?
O1 S1 C17 108.5(6) . . ?
O2 S1 C17 103.4(5) . . ?
O3 S1 C17 99.2(4) . . ?
F2 C17 F1 107.1(9) . . ?
F2 C17 F3 107.8(10) . . ?
F1 C17 F3 121.7(11) . . ?
F2 C17 S1 105.7(8) . . ?
F1 C17 S1 106.8(8) . . ?
F3 C17 S1 106.8(9) . . ?
O2' S1' O1' 110.0(14) . . ?
O2' S1' C17' 109.6(13) . . ?
O1' S1' C17' 108.3(12) . . ?
O2' S1' O3 110.0(10) . . ?
O1' S1' O3 120.5(8) . . ?
C17' S1' O3 97.4(7) . . ?
F3' C17' F2' 104.3(12) . . ?
F3' C17' F1' 115.5(14) . . ?
F2' C17' F1' 124.5(15) . . ?
F3' C17' S1' 108.7(13) . . ?
F2' C17' S1' 106.8(12) . . ?
F1' C17' S1' 95.7(12) . . ?
C2 O3 S1 127.0(4) . . ?
C2 O3 S1' 109.5(4) . . ?
C13 O4 C12 120.3(3) . . ?
C2 C1 C13 113.6(4) . . ?
C2 C1 Si1 127.9(4) . . ?
C13 C1 Si1 118.4(3) . . ?
C3 C2 C1 125.8(4) . . ?
C3 C2 O3 115.1(4) . . ?
C1 C2 O3 119.0(4) . . ?
C2 C3 C4 117.2(4) . . ?
C5 C4 C3 122.3(4) . . ?
C4 C5 C13 116.9(4) . . ?
C4 C5 C6 122.6(4) . . ?
C13 C5 C6 120.4(4) . . ?
C7 C6 C5 115.3(4) . . ?
C7 C6 C11 110.3(4) . . ?
C5 C6 C11 109.0(4) . . ?
C8 C7 C6 123.7(5) . . ?
C7 C8 C9 122.9(5) . . ?
C7 C8 C18 121.6(5) . . ?
C9 C8 C18 115.5(5) . . ?
C8 C9 C10 113.3(4) . . ?
C9 C10 C11 110.5(4) . . ?
C12 C11 C6 112.2(4) . . ?
C12 C11 C10 116.2(4) . . ?
C6 C11 C10 108.8(4) . . ?
O4 C12 C11 108.9(3) . . ?
O4 C12 C20 102.6(4) . . ?
C11 C12 C20 112.2(4) . . ?
O4 C12 C19 107.5(4) . . ?
C11 C12 C19 113.9(4) . . ?
C20 C12 C19 111.0(4) . . ?
O4 C13 C5 122.5(4) . . ?
O4 C13 C1 113.3(4) . . ?
C5 C13 C1 124.2(4) . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.040

