# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_mo_d8v19482_0m
_database_code_depnum_ccdc_archive 'CCDC 2120509'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,CAS
China
;
_audit_update_record             
;
2021-11-07 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 F O4 S2'
_chemical_formula_weight         292.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.4459(3)
_cell_length_b                   12.5540(5)
_cell_length_c                   13.0923(5)
_cell_angle_alpha                114.3620(10)
_cell_angle_beta                 102.2630(10)
_cell_angle_gamma                96.9760(10)
_cell_volume                     1343.37(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6143
_cell_measurement_theta_min      5.777
_cell_measurement_theta_max      54.709

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.411
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5617
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19071
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.447
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4987
_reflns_number_gt                3871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0335P)²+0.8384P] 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_number_reflns         4987
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
S1 S 0.42605(9) 0.56456(7) -0.19441(6) 0.0511(2) Uani 1 1 d . . . . .
S2 S 0.52973(8) 0.76156(6) 0.04799(6) 0.03744(18) Uani 1 1 d . . . . .
S3 S 0.60654(9) 0.09310(7) 0.35662(6) 0.0487(2) Uani 1 1 d . . . . .
S4 S 0.50938(7) 0.30339(6) 0.50779(6) 0.03949(19) Uani 1 1 d . . . . .
F1 F 0.3872(2) 0.43766(16) -0.20018(19) 0.0751(6) Uani 1 1 d . . . . .
F2 F 0.6650(2) 0.1147(2) 0.26294(19) 0.0958(8) Uani 1 1 d . . . . .
O1 O 0.7211(2) 0.52330(17) -0.13170(18) 0.0517(5) Uani 1 1 d . . . . .
O2 O 0.8153(2) 0.87024(16) 0.04757(17) 0.0480(5) Uani 1 1 d . . . . .
O3 O 0.4769(3) 0.5425(2) -0.29446(18) 0.0709(7) Uani 1 1 d . . . . .
O4 O 0.2940(2) 0.6065(2) -0.1901(2) 0.0746(8) Uani 1 1 d . . . . .
O5 O 0.3253(2) 0.0633(2) 0.18723(17) 0.0617(6) Uani 1 1 d . . . . .
O6 O 0.2069(2) 0.1640(2) 0.46338(19) 0.0574(6) Uani 1 1 d . . . . .
O7 O 0.5438(3) -0.0322(2) 0.3006(3) 0.0902(9) Uani 1 1 d . . . . .
O8 O 0.7324(2) 0.1415(2) 0.45710(19) 0.0661(7) Uani 1 1 d . . . . .
C1 C 0.5621(3) 0.6457(2) -0.0669(2) 0.0385(6) Uani 1 1 d . . . . .
C2 C 0.7042(3) 0.6148(2) -0.0545(2) 0.0390(6) Uani 1 1 d . . . . .
C3 C 0.8323(3) 0.6876(2) 0.0539(2) 0.0402(6) Uani 1 1 d . . . . .
C4 C 0.9091(3) 0.6248(3) 0.1035(3) 0.0550(8) Uani 1 1 d . . . . .
H4 H 0.8776 0.5415 0.0695 0.066 Uiso 1 1 calc R U . . .
C5 C 1.0302(4) 0.6823(3) 0.2014(3) 0.0681(10) Uani 1 1 d . . . . .
H5 H 1.0796 0.6385 0.2334 0.082 Uiso 1 1 calc R U . . .
C6 C 1.0776(4) 0.8055(3) 0.2516(3) 0.0658(9) Uani 1 1 d . . . . .
H6 H 1.1576 0.8452 0.3194 0.079 Uiso 1 1 calc R U . . .
C7 C 1.0080(3) 0.8706(3) 0.2028(3) 0.0535(8) Uani 1 1 d . . . . .
H7 H 1.0426 0.9536 0.2364 0.064 Uiso 1 1 calc R U . . .
C8 C 0.8863(3) 0.8124(2) 0.1036(2) 0.0405(6) Uani 1 1 d . . . . .
C9 C 0.8751(4) 0.9958(2) 0.0898(3) 0.0555(8) Uani 1 1 d . . . . .
H9A H 0.8628 1.0396 0.1660 0.083 Uiso 1 1 calc R U . . .
H9B H 0.8234 1.0227 0.0369 0.083 Uiso 1 1 calc R U . . .
H9C H 0.9791 1.0096 0.0950 0.083 Uiso 1 1 calc R U . . .
C10 C 0.4679(4) 0.8638(2) -0.0041(3) 0.0502(8) Uani 1 1 d . . . . .
H10A H 0.5426 0.8926 -0.0322 0.075 Uiso 1 1 calc R U . . .
H10B H 0.4510 0.9306 0.0586 0.075 Uiso 1 1 calc R U . . .
H10C H 0.3768 0.8233 -0.0668 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3655(4) 0.7085(3) 0.0768(3) 0.0571(8) Uani 1 1 d . . . . .
H11A H 0.2821 0.6793 0.0080 0.086 Uiso 1 1 calc R U . . .
H11B H 0.3472 0.7732 0.1404 0.086 Uiso 1 1 calc R U . . .
H11C H 0.3792 0.6446 0.0973 0.086 Uiso 1 1 calc R U . . .
C12 C 0.4778(3) 0.1759(2) 0.3788(2) 0.0378(6) Uani 1 1 d . . . . .
C13 C 0.3437(3) 0.1428(2) 0.2867(2) 0.0390(6) Uani 1 1 d . . . . .
C14 C 0.2241(3) 0.2103(2) 0.3099(2) 0.0380(6) Uani 1 1 d . . . . .
C15 C 0.1732(3) 0.2600(3) 0.2360(3) 0.0493(7) Uani 1 1 d . . . . .
H15 H 0.2156 0.2523 0.1761 0.059 Uiso 1 1 calc R U . . .
C16 C 0.0608(4) 0.3205(3) 0.2501(3) 0.0628(9) Uani 1 1 d . . . . .
H16 H 0.0287 0.3545 0.2008 0.075 Uiso 1 1 calc R U . . .
C17 C -0.0030(4) 0.3301(3) 0.3367(4) 0.0694(10) Uani 1 1 d . . . . .
H17 H -0.0790 0.3708 0.3462 0.083 Uiso 1 1 calc R U . . .
C18 C 0.0434(3) 0.2805(3) 0.4103(3) 0.0630(9) Uani 1 1 d . . . . .
H18 H -0.0014 0.2875 0.4688 0.076 Uiso 1 1 calc R U . . .
C19 C 0.1569(3) 0.2203(3) 0.3975(3) 0.0455(7) Uani 1 1 d . . . . .
C20 C 0.1369(4) 0.1647(4) 0.5503(3) 0.0842(12) Uani 1 1 d . . . . .
H20A H 0.1476 0.2462 0.6066 0.126 Uiso 1 1 calc R U . . .
H20B H 0.1832 0.1221 0.5892 0.126 Uiso 1 1 calc R U . . .
H20C H 0.0330 0.1261 0.5136 0.126 Uiso 1 1 calc R U . . .
C21 C 0.5574(4) 0.2661(3) 0.6261(2) 0.0548(8) Uani 1 1 d . . . . .
H21A H 0.4716 0.2159 0.6254 0.082 Uiso 1 1 calc R U . . .
H21B H 0.5908 0.3385 0.6989 0.082 Uiso 1 1 calc R U . . .
H21C H 0.6356 0.2238 0.6178 0.082 Uiso 1 1 calc R U . . .
C22 C 0.6794(3) 0.4029(3) 0.5328(3) 0.0644(9) Uani 1 1 d . . . . .
H22A H 0.7591 0.3622 0.5329 0.097 Uiso 1 1 calc R U . . .
H22B H 0.7012 0.4724 0.6071 0.097 Uiso 1 1 calc R U . . .
H22C H 0.6691 0.4275 0.4717 0.097 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 O4 1.414(2) . ?
S1 O3 1.422(2) . ?
S1 F1 1.557(2) . ?
S1 C1 1.686(3) . ?
S2 C1 1.724(2) . ?
S2 C10 1.786(3) . ?
S2 C11 1.787(3) . ?
S3 O7 1.415(2) . ?
S3 O8 1.419(2) . ?
S3 F2 1.552(2) . ?
S3 C12 1.689(3) . ?
S4 C12 1.715(2) . ?
S4 C21 1.782(3) . ?
S4 C22 1.788(3) . ?
O1 C2 1.234(3) . ?
O2 C8 1.366(3) . ?
O2 C9 1.429(3) . ?
O5 C13 1.229(3) . ?
O6 C19 1.369(3) . ?
O6 C20 1.431(4) . ?
C1 C2 1.437(4) . ?
C2 C3 1.498(4) . ?
C3 C4 1.390(4) . ?
C3 C8 1.401(4) . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(4) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.429(4) . ?
C13 C14 1.502(4) . ?
C14 C15 1.389(4) . ?
C14 C19 1.394(4) . ?
C15 C16 1.380(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(4) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O4 S1 O3 118.26(15) . . ?
O4 S1 F1 104.89(14) . . ?
O3 S1 F1 103.53(14) . . ?
O4 S1 C1 111.14(13) . . ?
O3 S1 C1 113.06(14) . . ?
F1 S1 C1 104.27(13) . . ?
C1 S2 C10 107.49(13) . . ?
C1 S2 C11 109.50(14) . . ?
C10 S2 C11 100.40(16) . . ?
O7 S3 O8 118.73(16) . . ?
O7 S3 F2 103.48(17) . . ?
O8 S3 F2 104.61(14) . . ?
O7 S3 C12 113.07(15) . . ?
O8 S3 C12 111.11(12) . . ?
F2 S3 C12 103.99(13) . . ?
C12 S4 C21 108.57(14) . . ?
C12 S4 C22 108.83(15) . . ?
C21 S4 C22 101.26(17) . . ?
C8 O2 C9 118.0(2) . . ?
C19 O6 C20 118.8(3) . . ?
C2 C1 S1 119.02(19) . . ?
C2 C1 S2 120.5(2) . . ?
S1 C1 S2 120.51(16) . . ?
O1 C2 C1 120.0(2) . . ?
O1 C2 C3 118.2(2) . . ?
C1 C2 C3 121.7(2) . . ?
C4 C3 C8 117.9(3) . . ?
C4 C3 C2 117.0(2) . . ?
C8 C3 C2 124.9(2) . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O2 C8 C7 123.3(3) . . ?
O2 C8 C3 116.5(2) . . ?
C7 C8 C3 120.2(3) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S2 C10 H10A 109.5 . . ?
S2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S2 C11 H11A 109.5 . . ?
S2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 S3 119.54(19) . . ?
C13 C12 S4 119.37(19) . . ?
S3 C12 S4 121.02(16) . . ?
O5 C13 C12 121.9(3) . . ?
O5 C13 C14 118.7(2) . . ?
C12 C13 C14 119.3(2) . . ?
C15 C14 C19 118.7(3) . . ?
C15 C14 C13 117.7(2) . . ?
C19 C14 C13 123.5(3) . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
O6 C19 C18 124.4(3) . . ?
O6 C19 C14 115.8(2) . . ?
C18 C19 C14 119.8(3) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S4 C21 H21A 109.5 . . ?
S4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S4 C22 H22A 109.5 . . ?
S4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 S1 C1 C2 179.1(2) . . . . ?
O3 S1 C1 C2 -45.1(3) . . . . ?
F1 S1 C1 C2 66.6(2) . . . . ?
O4 S1 C1 S2 0.7(2) . . . . ?
O3 S1 C1 S2 136.47(18) . . . . ?
F1 S1 C1 S2 -111.78(17) . . . . ?
C10 S2 C1 C2 125.3(2) . . . . ?
C11 S2 C1 C2 -126.5(2) . . . . ?
C10 S2 C1 S1 -56.3(2) . . . . ?
C11 S2 C1 S1 51.9(2) . . . . ?
S1 C1 C2 O1 -7.0(4) . . . . ?
S2 C1 C2 O1 171.5(2) . . . . ?
S1 C1 C2 C3 176.5(2) . . . . ?
S2 C1 C2 C3 -5.1(4) . . . . ?
O1 C2 C3 C4 -44.4(4) . . . . ?
C1 C2 C3 C4 132.3(3) . . . . ?
O1 C2 C3 C8 131.0(3) . . . . ?
C1 C2 C3 C8 -52.4(4) . . . . ?
C8 C3 C4 C5 2.9(5) . . . . ?
C2 C3 C4 C5 178.6(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 -2.0(6) . . . . ?
C5 C6 C7 C8 1.6(5) . . . . ?
C9 O2 C8 C7 3.6(4) . . . . ?
C9 O2 C8 C3 -174.7(2) . . . . ?
C6 C7 C8 O2 -177.3(3) . . . . ?
C6 C7 C8 C3 1.0(4) . . . . ?
C4 C3 C8 O2 175.2(2) . . . . ?
C2 C3 C8 O2 -0.1(4) . . . . ?
C4 C3 C8 C7 -3.2(4) . . . . ?
C2 C3 C8 C7 -178.6(3) . . . . ?
O7 S3 C12 C13 -44.7(3) . . . . ?
O8 S3 C12 C13 178.9(2) . . . . ?
F2 S3 C12 C13 66.8(2) . . . . ?
O7 S3 C12 S4 138.4(2) . . . . ?
O8 S3 C12 S4 2.0(2) . . . . ?
F2 S3 C12 S4 -110.03(19) . . . . ?
C21 S4 C12 C13 129.3(2) . . . . ?
C22 S4 C12 C13 -121.3(2) . . . . ?
C21 S4 C12 S3 -53.8(2) . . . . ?
C22 S4 C12 S3 55.6(2) . . . . ?
S3 C12 C13 O5 -7.9(4) . . . . ?
S4 C12 C13 O5 169.1(2) . . . . ?
S3 C12 C13 C14 174.9(2) . . . . ?
S4 C12 C13 C14 -8.2(4) . . . . ?
O5 C13 C14 C15 -51.5(4) . . . . ?
C12 C13 C14 C15 125.8(3) . . . . ?
O5 C13 C14 C19 125.2(3) . . . . ?
C12 C13 C14 C19 -57.5(4) . . . . ?
C19 C14 C15 C16 1.4(4) . . . . ?
C13 C14 C15 C16 178.3(3) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C20 O6 C19 C18 1.2(5) . . . . ?
C20 O6 C19 C14 -176.4(3) . . . . ?
C17 C18 C19 O6 -177.4(3) . . . . ?
C17 C18 C19 C14 0.1(5) . . . . ?
C15 C14 C19 O6 176.7(2) . . . . ?
C13 C14 C19 O6 0.1(4) . . . . ?
C15 C14 C19 C18 -1.0(4) . . . . ?
C13 C14 C19 C18 -177.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H22C O3 0.96 2.63 3.527(4) 155.6 2_665
C22 H22A O8 0.96 2.49 3.152(4) 126.3 .
C21 H21C O8 0.96 2.36 3.067(4) 129.8 .
C21 H21B O1 0.96 2.39 3.336(4) 167.8 1_556
C11 H11C O1 0.96 2.45 3.325(4) 150.8 2_665
C11 H11B O7 0.96 2.61 3.274(4) 126.3 1_565
C11 H11A O4 0.96 2.40 3.066(4) 125.9 .
C10 H10C O4 0.96 2.44 3.096(4) 125.5 .
C10 H10B O5 0.96 2.46 3.382(3) 161.6 1_565
C9 H9B O5 0.96 2.65 3.437(4) 139.6 2_665
C9 H9A F2 0.96 2.54 3.337(4) 140.8 1_565

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mo_d8v20433_0m
_database_code_depnum_ccdc_archive 'CCDC 2120512'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,CAS
China
;
_audit_update_record             
;
2021-11-07 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 F N O5 S'
_chemical_formula_weight         345.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4205(19)
_cell_length_b                   19.723(5)
_cell_length_c                   10.592(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.954(6)
_cell_angle_gamma                90
_cell_volume                     1673.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3675
_cell_measurement_theta_min      5.091
_cell_measurement_theta_max      54.390

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16281
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.021
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.040
_diffrn_measured_fraction_theta_full 1.013
_diffrn_reflns_Laue_measured_fraction_max 1.040
_diffrn_reflns_Laue_measured_fraction_full 1.013
_diffrn_reflns_point_group_measured_fraction_max 1.040
_diffrn_reflns_point_group_measured_fraction_full 1.013
_reflns_number_total             2942
_reflns_number_gt                1963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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_number_reflns         2942
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1779
_refine_ls_R_factor_gt           0.1343
_refine_ls_wR_factor_ref         0.4419
_refine_ls_wR_factor_gt          0.4049
_refine_ls_goodness_of_fit_ref   1.676
_refine_ls_restrained_S_all      1.676
_refine_ls_shift/su_max          0.004
_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
S1 S 0.6538(3) 0.17457(12) 0.3125(2) 0.0591(9) Uani 1 1 d . . . . .
F1 F 0.7293(9) 0.1974(4) 0.2010(7) 0.096(2) Uani 1 1 d . . . . .
O1 O 0.4054(9) 0.2863(3) 0.4392(6) 0.0632(18) Uani 1 1 d . . . . .
O2 O 0.7404(8) 0.5050(3) 0.4525(6) 0.0589(17) Uani 1 1 d . . . . .
O3 O 0.7603(9) 0.5147(3) 0.2126(6) 0.0647(18) Uani 1 1 d . . . . .
O4 O 0.7676(10) 0.1995(5) 0.4290(8) 0.095(3) Uani 1 1 d . . . . .
O5 O 0.6372(9) 0.1038(4) 0.2941(8) 0.085(2) Uani 1 1 d . . . . .
N1 N 0.1766(9) 0.2015(3) 0.1583(7) 0.0510(18) Uani 1 1 d . . . . .
C1 C 0.5762(14) 0.3461(5) 0.1892(10) 0.065(3) Uani 1 1 d . . . . .
H1 H 0.5425 0.3106 0.1289 0.079 Uiso 1 1 calc R U . . .
C2 C 0.6384(13) 0.4034(5) 0.1524(10) 0.069(3) Uani 1 1 d . . . . .
H2 H 0.6434 0.4078 0.0662 0.082 Uiso 1 1 calc R U . . .
C3 C 0.6951(11) 0.4561(4) 0.2430(9) 0.053(2) Uani 1 1 d . . . . .
C4 C 0.6815(10) 0.4512(4) 0.3689(9) 0.049(2) Uani 1 1 d . . . . .
C5 C 0.6114(11) 0.3936(4) 0.4048(8) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.5970 0.3908 0.4883 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5623(12) 0.3396(4) 0.3153(8) 0.051(2) Uani 1 1 d . . . . .
C7 C 0.4753(11) 0.2817(4) 0.3524(9) 0.051(2) Uani 1 1 d . . . . .
C8 C 0.4713(10) 0.2150(4) 0.2815(9) 0.049(2) Uani 1 1 d . . . . .
C9 C 0.3328(10) 0.1795(4) 0.2032(9) 0.053(2) Uani 1 1 d . . . . .
H9 H 0.3520 0.1355 0.1798 0.063 Uiso 1 1 calc R U . . .
C10 C 0.1253(15) 0.2704(5) 0.1777(13) 0.088(4) Uani 1 1 d . . . . .
H10A H 0.1385 0.2775 0.2700 0.131 Uiso 1 1 calc R U . . .
H10B H 0.0104 0.2768 0.1268 0.131 Uiso 1 1 calc R U . . .
H10C H 0.1934 0.3023 0.1491 0.131 Uiso 1 1 calc R U . . .
C11 C 0.0430(13) 0.1552(5) 0.0797(14) 0.079(3) Uani 1 1 d . . . . .
H11A H 0.0324 0.1595 -0.0128 0.118 Uiso 1 1 calc R U . . .
H11B H -0.0610 0.1670 0.0936 0.118 Uiso 1 1 calc R U . . .
H11C H 0.0714 0.1093 0.1076 0.118 Uiso 1 1 calc R U . . .
C12 C 0.7484(12) 0.4982(5) 0.5868(8) 0.056(2) Uani 1 1 d . . . . .
H12A H 0.8135 0.4583 0.6241 0.068 Uiso 1 1 calc R U . . .
H12B H 0.6368 0.4922 0.5931 0.068 Uiso 1 1 calc R U . . .
C13 C 0.8270(14) 0.5596(6) 0.6642(11) 0.078(3) Uani 1 1 d . . . . .
H13A H 0.7473 0.5960 0.6465 0.117 Uiso 1 1 calc R U . . .
H13B H 0.9221 0.5730 0.6384 0.117 Uiso 1 1 calc R U . . .
H13C H 0.8618 0.5493 0.7573 0.117 Uiso 1 1 calc R U . . .
C14 C 0.7783(14) 0.5206(6) 0.0817(10) 0.069(3) Uani 1 1 d . . . . .
H14A H 0.6696 0.5200 0.0147 0.083 Uiso 1 1 calc R U . . .
H14B H 0.8436 0.4831 0.0650 0.083 Uiso 1 1 calc R U . . .
C15 C 0.8658(19) 0.5872(7) 0.0772(12) 0.098(4) Uani 1 1 d . . . . .
H15A H 0.8998 0.5888 -0.0014 0.147 Uiso 1 1 calc R U . . .
H15B H 0.9622 0.5910 0.1541 0.147 Uiso 1 1 calc R U . . .
H15C H 0.7909 0.6240 0.0759 0.147 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 O4 1.397(8) . ?
S1 O5 1.410(8) . ?
S1 F1 1.570(7) . ?
S1 C8 1.671(8) . ?
O1 C7 1.238(10) . ?
O2 C4 1.373(10) . ?
O2 C12 1.410(11) . ?
O3 C3 1.361(10) . ?
O3 C14 1.445(11) . ?
N1 C9 1.326(11) . ?
N1 C10 1.459(11) . ?
N1 C11 1.489(12) . ?
C1 C2 1.353(13) . ?
C1 C6 1.383(13) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(13) . ?
C4 C5 1.386(12) . ?
C5 C6 1.401(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.474(12) . ?
C7 C8 1.509(12) . ?
C8 C9 1.394(12) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.498(13) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.514(16) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O5 118.8(5) . . ?
O4 S1 F1 103.7(5) . . ?
O5 S1 F1 103.0(5) . . ?
O4 S1 C8 110.1(5) . . ?
O5 S1 C8 113.5(4) . . ?
F1 S1 C8 106.0(4) . . ?
C4 O2 C12 118.1(7) . . ?
C3 O3 C14 117.7(7) . . ?
C9 N1 C10 124.0(7) . . ?
C9 N1 C11 119.6(8) . . ?
C10 N1 C11 116.4(8) . . ?
C2 C1 C6 120.7(9) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.3(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O3 C3 C4 116.7(8) . . ?
O3 C3 C2 123.1(8) . . ?
C4 C3 C2 120.1(8) . . ?
O2 C4 C3 116.7(7) . . ?
O2 C4 C5 123.8(8) . . ?
C3 C4 C5 119.5(8) . . ?
C4 C5 C6 120.0(8) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.2(8) . . ?
C1 C6 C7 121.7(8) . . ?
C5 C6 C7 118.5(8) . . ?
O1 C7 C6 121.9(7) . . ?
O1 C7 C8 119.4(8) . . ?
C6 C7 C8 118.7(8) . . ?
C9 C8 C7 128.3(8) . . ?
C9 C8 S1 115.3(6) . . ?
C7 C8 S1 116.1(6) . . ?
N1 C9 C8 127.2(8) . . ?
N1 C9 H9 116.4 . . ?
C8 C9 H9 116.4 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 110.5(8) . . ?
O2 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 C15 107.2(9) . . ?
O3 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O3 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.3(17) . . . . ?
C14 O3 C3 C4 179.1(8) . . . . ?
C14 O3 C3 C2 -3.0(13) . . . . ?
C1 C2 C3 O3 179.4(9) . . . . ?
C1 C2 C3 C4 -2.8(15) . . . . ?
C12 O2 C4 C3 -171.9(8) . . . . ?
C12 O2 C4 C5 7.8(12) . . . . ?
O3 C3 C4 O2 -2.2(12) . . . . ?
C2 C3 C4 O2 179.9(8) . . . . ?
O3 C3 C4 C5 178.1(7) . . . . ?
C2 C3 C4 C5 0.1(13) . . . . ?
O2 C4 C5 C6 -176.7(8) . . . . ?
C3 C4 C5 C6 3.0(13) . . . . ?
C2 C1 C6 C5 0.8(17) . . . . ?
C2 C1 C6 C7 171.9(9) . . . . ?
C4 C5 C6 C1 -3.5(14) . . . . ?
C4 C5 C6 C7 -174.9(8) . . . . ?
C1 C6 C7 O1 -151.4(10) . . . . ?
C5 C6 C7 O1 19.7(13) . . . . ?
C1 C6 C7 C8 28.4(13) . . . . ?
C5 C6 C7 C8 -160.5(8) . . . . ?
O1 C7 C8 C9 61.5(13) . . . . ?
C6 C7 C8 C9 -118.4(10) . . . . ?
O1 C7 C8 S1 -111.9(8) . . . . ?
C6 C7 C8 S1 68.3(10) . . . . ?
O4 S1 C8 C9 -156.0(8) . . . . ?
O5 S1 C8 C9 -20.0(9) . . . . ?
F1 S1 C8 C9 92.4(8) . . . . ?
O4 S1 C8 C7 18.2(9) . . . . ?
O5 S1 C8 C7 154.3(7) . . . . ?
F1 S1 C8 C7 -93.3(7) . . . . ?
C10 N1 C9 C8 4.2(15) . . . . ?
C11 N1 C9 C8 -177.7(10) . . . . ?
C7 C8 C9 N1 10.7(15) . . . . ?
S1 C8 C9 N1 -175.9(7) . . . . ?
C4 O2 C12 C13 175.9(8) . . . . ?
C3 O3 C14 C15 -175.4(9) . . . . ?

_refine_diff_density_max         0.923
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.127

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v20436
_database_code_depnum_ccdc_archive 'CCDC 2120511'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,CAS
China
;
_audit_update_record             
;
2021-11-07 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 F N O5 S'
_chemical_formula_weight         385.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.521(11)
_cell_length_b                   13.867(12)
_cell_length_c                   11.473(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.55(2)
_cell_angle_gamma                90
_cell_volume                     1958(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5341
_cell_measurement_theta_min      4.425
_cell_measurement_theta_max      45.526

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.202
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4846
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45750
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.657
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3635
_reflns_number_gt                2279
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0556P)²+0.9626P] 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_number_reflns         3635
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
S1 S 0.35462(8) 0.91270(6) 0.62335(8) 0.0613(3) Uani 1 1 d . . . . .
F1 F 0.4174(2) 0.94977(17) 0.7460(2) 0.1018(8) Uani 1 1 d . . . . .
O1 O 0.3821(2) 0.73030(16) 0.78237(17) 0.0664(7) Uani 1 1 d . . . . .
O2 O 0.20165(19) 0.40312(15) 0.67956(17) 0.0585(6) Uani 1 1 d . . . . .
O3 O 0.12999(18) 0.40806(14) 0.45384(16) 0.0550(6) Uani 1 1 d . . . . .
O4 O 0.2462(2) 0.9014(2) 0.6435(2) 0.0885(9) Uani 1 1 d . . . . .
O5 O 0.3770(3) 0.98260(18) 0.5403(2) 0.0903(9) Uani 1 1 d . . . . .
N1 N 0.5557(2) 0.73340(18) 0.5108(2) 0.0507(6) Uani 1 1 d . . . . .
C1 C 0.2715(2) 0.6436(2) 0.4894(2) 0.0429(7) Uani 1 1 d . . . . .
H1 H 0.2862 0.6966 0.4453 0.051 Uiso 1 1 calc R U . . .
C2 C 0.2097(2) 0.5676(2) 0.4338(2) 0.0468(7) Uani 1 1 d . . . . .
H2 H 0.1829 0.5704 0.3527 0.056 Uiso 1 1 calc R U . . .
C3 C 0.1878(2) 0.4873(2) 0.4989(2) 0.0428(7) Uani 1 1 d . . . . .
C4 C 0.2284(2) 0.4843(2) 0.6225(2) 0.0422(7) Uani 1 1 d . . . . .
C5 C 0.2897(2) 0.5599(2) 0.6766(2) 0.0410(7) Uani 1 1 d . . . . .
H5 H 0.3171 0.5575 0.7576 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3110(2) 0.64077(19) 0.6101(2) 0.0381(6) Uani 1 1 d . . . . .
C7 C 0.3711(2) 0.7232(2) 0.6745(2) 0.0428(7) Uani 1 1 d . . . . .
C8 C 0.4114(2) 0.8032(2) 0.6047(2) 0.0409(7) Uani 1 1 d . . . . .
C9 C 0.4891(2) 0.8031(2) 0.5329(2) 0.0442(7) Uani 1 1 d . . . . .
H9 H 0.4958 0.8609 0.4938 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5578(3) 0.6366(2) 0.5601(3) 0.0697(10) Uani 1 1 d . . . . .
H10A H 0.5396 0.6394 0.6378 0.105 Uiso 1 1 calc R U . . .
H10B H 0.6292 0.6097 0.5654 0.105 Uiso 1 1 calc R U . . .
H10C H 0.5060 0.5968 0.5097 0.105 Uiso 1 1 calc R U . . .
C11 C 0.6257(3) 0.7490(3) 0.4227(3) 0.0745(11) Uani 1 1 d . . . . .
H11A H 0.6020 0.7084 0.3552 0.112 Uiso 1 1 calc R U . . .
H11B H 0.6994 0.7336 0.4572 0.112 Uiso 1 1 calc R U . . .
H11C H 0.6213 0.8153 0.3982 0.112 Uiso 1 1 calc R U . . .
C12 C 0.2388(4) 0.3989(3) 0.8050(3) 0.0861(13) Uani 1 1 d . . . . .
H12A H 0.3166 0.4034 0.8221 0.129 Uiso 1 1 calc R U . . .
H12B H 0.2166 0.3389 0.8349 0.129 Uiso 1 1 calc R U . . .
H12C H 0.2081 0.4514 0.8423 0.129 Uiso 1 1 calc R U . . .
C13 C 0.0722(2) 0.4082(2) 0.3313(2) 0.0473(7) Uani 1 1 d . . . . .
H13 H 0.0393 0.4718 0.3121 0.057 Uiso 1 1 calc R U . . .
C14 C -0.0167(3) 0.3334(3) 0.3259(3) 0.0595(9) Uani 1 1 d . . . . .
H14A H -0.0644 0.3513 0.3801 0.071 Uiso 1 1 calc R U . . .
H14B H 0.0155 0.2714 0.3509 0.071 Uiso 1 1 calc R U . . .
C15 C -0.0830(3) 0.3247(3) 0.2003(3) 0.0827(12) Uani 1 1 d . . . . .
H15A H -0.1356 0.2731 0.1981 0.099 Uiso 1 1 calc R U . . .
H15B H -0.1225 0.3843 0.1793 0.099 Uiso 1 1 calc R U . . .
C16 C -0.0113(3) 0.3043(3) 0.1105(3) 0.0845(12) Uani 1 1 d . . . . .
H16A H -0.0549 0.3057 0.0314 0.101 Uiso 1 1 calc R U . . .
H16B H 0.0195 0.2402 0.1240 0.101 Uiso 1 1 calc R U . . .
C17 C 0.0803(3) 0.3775(3) 0.1181(3) 0.0800(12) Uani 1 1 d . . . . .
H17A H 0.0501 0.4404 0.0939 0.096 Uiso 1 1 calc R U . . .
H17B H 0.1280 0.3590 0.0641 0.096 Uiso 1 1 calc R U . . .
C18 C 0.1460(3) 0.3839(3) 0.2441(3) 0.0599(9) Uani 1 1 d . . . . .
H18A H 0.1819 0.3229 0.2658 0.072 Uiso 1 1 calc R U . . .
H18B H 0.2014 0.4333 0.2475 0.072 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 O5 1.422(3) . ?
S1 O4 1.427(3) . ?
S1 F1 1.568(2) . ?
S1 C8 1.707(3) . ?
O1 C7 1.224(3) . ?
O2 C4 1.375(3) . ?
O2 C12 1.431(4) . ?
O3 C3 1.364(3) . ?
O3 C13 1.459(3) . ?
N1 C9 1.331(4) . ?
N1 C10 1.456(4) . ?
N1 C11 1.469(4) . ?
C1 C6 1.383(4) . ?
C1 C2 1.391(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.417(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.410(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(4) . ?
C7 C8 1.508(4) . ?
C8 C9 1.385(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.514(4) . ?
C13 C18 1.519(4) . ?
C13 H13 0.9800 . ?
C14 C15 1.531(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.512(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.522(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.530(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
O5 S1 O4 119.57(18) . . ?
O5 S1 F1 104.47(18) . . ?
O4 S1 F1 103.08(17) . . ?
O5 S1 C8 112.64(15) . . ?
O4 S1 C8 110.67(16) . . ?
F1 S1 C8 104.59(14) . . ?
C4 O2 C12 116.8(2) . . ?
C3 O3 C13 119.9(2) . . ?
C9 N1 C10 124.3(3) . . ?
C9 N1 C11 119.8(3) . . ?
C10 N1 C11 115.7(3) . . ?
C6 C1 C2 120.3(3) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O3 C3 C2 125.7(2) . . ?
O3 C3 C4 115.1(2) . . ?
C2 C3 C4 119.2(3) . . ?
O2 C4 C5 124.9(2) . . ?
O2 C4 C3 115.2(2) . . ?
C5 C4 C3 119.8(3) . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 C7 122.1(2) . . ?
C5 C6 C7 118.1(2) . . ?
O1 C7 C6 121.1(3) . . ?
O1 C7 C8 119.4(3) . . ?
C6 C7 C8 119.3(2) . . ?
C9 C8 C7 130.9(3) . . ?
C9 C8 S1 115.4(2) . . ?
C7 C8 S1 113.6(2) . . ?
N1 C9 C8 130.3(3) . . ?
N1 C9 H9 114.8 . . ?
C8 C9 H9 114.8 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 105.6(2) . . ?
O3 C13 C18 112.3(3) . . ?
C14 C13 C18 110.6(3) . . ?
O3 C13 H13 109.4 . . ?
C14 C13 H13 109.4 . . ?
C18 C13 H13 109.4 . . ?
C13 C14 C15 111.1(3) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 111.7(3) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 111.8(3) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 111.2(3) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C13 C18 C17 110.4(3) . . ?
C13 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
C13 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(4) . . . . ?
C13 O3 C3 C2 -8.7(4) . . . . ?
C13 O3 C3 C4 171.9(2) . . . . ?
C1 C2 C3 O3 -178.9(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C12 O2 C4 C5 1.4(4) . . . . ?
C12 O2 C4 C3 -178.4(3) . . . . ?
O3 C3 C4 O2 -1.4(4) . . . . ?
C2 C3 C4 O2 179.2(3) . . . . ?
O3 C3 C4 C5 178.8(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
O2 C4 C5 C6 -178.9(3) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C1 C6 C7 -175.9(3) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C4 C5 C6 C7 175.9(3) . . . . ?
C1 C6 C7 O1 161.7(3) . . . . ?
C5 C6 C7 O1 -15.0(4) . . . . ?
C1 C6 C7 C8 -13.4(4) . . . . ?
C5 C6 C7 C8 169.9(2) . . . . ?
O1 C7 C8 C9 119.0(4) . . . . ?
C6 C7 C8 C9 -65.8(4) . . . . ?
O1 C7 C8 S1 -58.0(3) . . . . ?
C6 C7 C8 S1 117.2(2) . . . . ?
O5 S1 C8 C9 14.0(3) . . . . ?
O4 S1 C8 C9 150.7(2) . . . . ?
F1 S1 C8 C9 -98.9(2) . . . . ?
O5 S1 C8 C7 -168.5(2) . . . . ?
O4 S1 C8 C7 -31.7(3) . . . . ?
F1 S1 C8 C7 78.6(2) . . . . ?
C10 N1 C9 C8 1.3(5) . . . . ?
C11 N1 C9 C8 175.1(3) . . . . ?
C7 C8 C9 N1 -4.9(5) . . . . ?
S1 C8 C9 N1 172.1(2) . . . . ?
C3 O3 C13 C14 -156.9(3) . . . . ?
C3 O3 C13 C18 82.4(3) . . . . ?
O3 C13 C14 C15 -178.9(3) . . . . ?
C18 C13 C14 C15 -57.1(4) . . . . ?
C13 C14 C15 C16 54.8(4) . . . . ?
C14 C15 C16 C17 -53.3(5) . . . . ?
C15 C16 C17 C18 54.2(5) . . . . ?
O3 C13 C18 C17 175.7(3) . . . . ?
C14 C13 C18 C17 58.0(4) . . . . ?
C16 C17 C18 C13 -56.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O5 0.93 2.37 2.867(4) 112.9 .
C9 H9 O5 0.93 2.37 2.867(4) 112.9 .

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4



