# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_201106e
_database_code_depnum_ccdc_archive 'CCDC 2052127'
loop_
_audit_author_name
_audit_author_address
'longzhou qin'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-12-23 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 F3 O3 S2'
_chemical_formula_weight         450.48

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0894(8)
_cell_length_b                   8.6805(9)
_cell_length_c                   16.3072(15)
_cell_angle_alpha                80.083(2)
_cell_angle_beta                 79.0770(10)
_cell_angle_gamma                79.4930(10)
_cell_volume                     1094.20(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1566
_cell_measurement_theta_min      2.571
_cell_measurement_theta_max      21.644

_exptl_crystal_description       locked
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9007
_exptl_absorpt_correction_T_max  0.9580
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5552
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3786
_reflns_number_gt                2275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1817P)²+0.0007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3786
_refine_ls_number_parameters     261
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0911
_refine_ls_wR_factor_ref         0.3079
_refine_ls_wR_factor_gt          0.2679
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3104(6) 0.4101(6) 0.0991(3) 0.1284(18) Uani 1 1 d . . .
F2 F 0.5137(9) 0.5146(7) 0.1159(4) 0.162(3) Uani 1 1 d . . .
F3 F 0.5644(8) 0.2992(8) 0.0640(3) 0.147(2) Uani 1 1 d . . .
O1 O 0.6293(5) 0.2525(5) 0.2429(3) 0.0839(13) Uani 1 1 d . . .
O2 O 0.3356(7) 0.3682(7) 0.2784(3) 0.114(2) Uani 1 1 d . . .
O3 O 0.4074(6) 0.1208(6) 0.2205(4) 0.1030(16) Uani 1 1 d . . .
S1 S 1.12854(17) -0.07321(17) 0.23382(9) 0.0610(5) Uani 1 1 d . . .
S2 S 0.45763(18) 0.26903(18) 0.22800(10) 0.0662(5) Uani 1 1 d . . .
C1 C 1.0391(7) 0.0501(7) 0.3047(3) 0.0648(14) Uani 1 1 d . . .
C2 C 0.9774(8) 0.1183(7) 0.3634(3) 0.0647(14) Uani 1 1 d . . .
C3 C 0.8974(8) 0.2005(7) 0.4331(3) 0.0712(16) Uani 1 1 d . . .
C4 C 0.9925(10) 0.2488(8) 0.4829(4) 0.0827(17) Uani 1 1 d U . .
C5 C 0.9060(14) 0.3315(9) 0.5489(4) 0.101(3) Uani 1 1 d . . .
H5 H 0.9681 0.3690 0.5817 0.122 Uiso 1 1 calc R . .
C6 C 0.7323(15) 0.3581(10) 0.5660(5) 0.112(3) Uani 1 1 d . . .
H6 H 0.6780 0.4048 0.6133 0.135 Uiso 1 1 calc R . .
C7 C 0.6387(13) 0.3177(13) 0.5157(7) 0.140(4) Uani 1 1 d . . .
H7 H 0.5206 0.3429 0.5260 0.168 Uiso 1 1 calc R . .
C8 C 0.7178(12) 0.2386(12) 0.4485(6) 0.123(3) Uani 1 1 d . . .
H8 H 0.6530 0.2107 0.4135 0.147 Uiso 1 1 calc R . .
C9 C 1.1830(11) 0.2008(12) 0.4727(5) 0.119(3) Uani 1 1 d U . .
H9A H 1.2110 0.0891 0.4704 0.179 Uiso 1 1 calc R . .
H9B H 1.2239 0.2251 0.5198 0.179 Uiso 1 1 calc R . .
H9C H 1.2354 0.2576 0.4214 0.179 Uiso 1 1 calc R . .
C10 C 1.1219(5) 0.0445(5) 0.1323(2) 0.0653(15) Uani 1 1 d G . .
C11 C 1.2427(5) -0.0124(6) 0.0656(3) 0.0804(18) Uani 1 1 d G . .
H11 H 1.3204 -0.1039 0.0755 0.096 Uiso 1 1 calc R . .
C12 C 1.2432(6) 0.0701(6) -0.0139(3) 0.097(2) Uani 1 1 d G . .
H12 H 1.3220 0.0346 -0.0588 0.117 Uiso 1 1 calc R . .
C13 C 1.1276(7) 0.2052(6) -0.0276(2) 0.088(2) Uani 1 1 d G . .
H13 H 1.1313 0.2621 -0.0816 0.106 Uiso 1 1 calc R . .
C14 C 1.0054(6) 0.2584(5) 0.0376(3) 0.087(2) Uani 1 1 d G . .
H14 H 0.9263 0.3485 0.0268 0.104 Uiso 1 1 calc R . .
C15 C 1.0015(5) 0.1767(5) 0.1190(2) 0.0744(17) Uani 1 1 d G . .
H15 H 0.9199 0.2104 0.1632 0.089 Uiso 1 1 calc R . .
C16 C 0.9668(7) -0.1950(6) 0.2448(3) 0.0524(12) Uani 1 1 d . . .
C17 C 1.0244(9) -0.3550(8) 0.2446(4) 0.0760(18) Uani 1 1 d . . .
H17 H 1.1403 -0.3941 0.2382 0.091 Uiso 1 1 calc R . .
C18 C 0.9052(13) -0.4559(8) 0.2543(4) 0.094(2) Uani 1 1 d . . .
H18 H 0.9415 -0.5637 0.2535 0.113 Uiso 1 1 calc R . .
C19 C 0.7351(11) -0.3980(8) 0.2649(4) 0.085(2) Uani 1 1 d . . .
H19 H 0.6562 -0.4668 0.2719 0.102 Uiso 1 1 calc R . .
C20 C 0.6788(9) -0.2362(8) 0.2654(4) 0.0814(18) Uani 1 1 d . . .
H20 H 0.5629 -0.1971 0.2729 0.098 Uiso 1 1 calc R . .
C21 C 0.7954(7) -0.1359(6) 0.2547(3) 0.0608(13) Uani 1 1 d . . .
H21 H 0.7591 -0.0278 0.2541 0.073 Uiso 1 1 calc R . .
C22 C 0.4665(10) 0.3802(11) 0.1222(5) 0.096(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
F1 C22 1.353(8) . ?
F2 C22 1.275(10) . ?
F3 C22 1.328(8) . ?
O1 S2 1.432(4) . ?
O2 S2 1.420(4) . ?
O3 S2 1.448(5) . ?
S1 C1 1.682(6) . ?
S1 C16 1.792(5) . ?
S1 C10 1.793(4) . ?
S2 C22 1.821(8) . ?
C1 C2 1.194(8) . ?
C2 C3 1.432(8) . ?
C3 C4 1.377(9) . ?
C3 C8 1.414(10) . ?
C4 C5 1.400(10) . ?
C4 C9 1.506(11) . ?
C5 C6 1.364(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.342(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(10) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.378(3) . ?
C10 C11 1.410(3) . ?
C11 C12 1.369(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.377(7) . ?
C16 C17 1.382(8) . ?
C17 C18 1.387(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(8) . ?
C20 H20 0.9300 . ?
C21 H21 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
C1 S1 C16 101.1(3) . . ?
C1 S1 C10 105.6(2) . . ?
C16 S1 C10 104.4(2) . . ?
O2 S2 O1 115.2(3) . . ?
O2 S2 O3 115.3(4) . . ?
O1 S2 O3 113.4(3) . . ?
O2 S2 C22 103.5(3) . . ?
O1 S2 C22 102.9(3) . . ?
O3 S2 C22 104.4(4) . . ?
C2 C1 S1 170.5(5) . . ?
C1 C2 C3 178.0(6) . . ?
C4 C3 C8 119.6(7) . . ?
C4 C3 C2 121.2(6) . . ?
C8 C3 C2 119.1(6) . . ?
C3 C4 C5 118.2(7) . . ?
C3 C4 C9 121.3(7) . . ?
C5 C4 C9 120.2(7) . . ?
C6 C5 C4 121.2(8) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C6 C5 120.9(8) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.1(10) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 119.7(9) . . ?
C7 C8 H8 120.1 . . ?
C3 C8 H8 120.1 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 121.8 . . ?
C15 C10 S1 122.7(2) . . ?
C11 C10 S1 115.4(2) . . ?
C12 C11 C10 118.6 . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 120.1 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 121.3 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 119.9 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 118.3 . . ?
C10 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C21 C16 C17 121.2(5) . . ?
C21 C16 S1 123.0(4) . . ?
C17 C16 S1 115.7(5) . . ?
C16 C17 C18 118.5(6) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C19 C18 C17 120.5(6) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.4(6) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 119.4(6) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C16 119.9(5) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
F2 C22 F3 109.4(8) . . ?
F2 C22 F1 105.9(7) . . ?
F3 C22 F1 104.6(6) . . ?
F2 C22 S2 113.4(6) . . ?
F3 C22 S2 112.5(6) . . ?
F1 C22 S2 110.4(6) . . ?

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
C16 S1 C1 C2 64(3) . . . . ?
C10 S1 C1 C2 173(3) . . . . ?
S1 C1 C2 C3 -104(17) . . . . ?
C1 C2 C3 C4 -173(18) . . . . ?
C1 C2 C3 C8 5(18) . . . . ?
C8 C3 C4 C5 1.6(10) . . . . ?
C2 C3 C4 C5 178.7(6) . . . . ?
C8 C3 C4 C9 175.6(7) . . . . ?
C2 C3 C4 C9 -7.3(10) . . . . ?
C3 C4 C5 C6 2.7(10) . . . . ?
C9 C4 C5 C6 -171.3(8) . . . . ?
C4 C5 C6 C7 -5.8(14) . . . . ?
C5 C6 C7 C8 4.3(17) . . . . ?
C6 C7 C8 C3 0.0(17) . . . . ?
C4 C3 C8 C7 -3.0(13) . . . . ?
C2 C3 C8 C7 179.8(9) . . . . ?
C1 S1 C10 C15 -26.5(3) . . . . ?
C16 S1 C10 C15 79.6(3) . . . . ?
C1 S1 C10 C11 156.9(3) . . . . ?
C16 S1 C10 C11 -96.9(3) . . . . ?
C15 C10 C11 C12 2.3 . . . . ?
S1 C10 C11 C12 178.9(3) . . . . ?
C10 C11 C12 C13 -0.1 . . . . ?
C11 C12 C13 C14 -1.9 . . . . ?
C12 C13 C14 C15 1.7 . . . . ?
C11 C10 C15 C14 -2.5 . . . . ?
S1 C10 C15 C14 -178.9(3) . . . . ?
C13 C14 C15 C10 0.5 . . . . ?
C1 S1 C16 C21 40.4(5) . . . . ?
C10 S1 C16 C21 -69.0(5) . . . . ?
C1 S1 C16 C17 -138.1(4) . . . . ?
C10 S1 C16 C17 112.4(4) . . . . ?
C21 C16 C17 C18 0.4(8) . . . . ?
S1 C16 C17 C18 179.0(4) . . . . ?
C16 C17 C18 C19 -1.0(9) . . . . ?
C17 C18 C19 C20 0.7(10) . . . . ?
C18 C19 C20 C21 0.3(10) . . . . ?
C19 C20 C21 C16 -0.9(9) . . . . ?
C17 C16 C21 C20 0.6(8) . . . . ?
S1 C16 C21 C20 -177.9(4) . . . . ?
O2 S2 C22 F2 60.7(7) . . . . ?
O1 S2 C22 F2 -59.6(7) . . . . ?
O3 S2 C22 F2 -178.2(6) . . . . ?
O2 S2 C22 F3 -174.4(6) . . . . ?
O1 S2 C22 F3 65.3(7) . . . . ?
O3 S2 C22 F3 -53.4(7) . . . . ?
O2 S2 C22 F1 -58.0(7) . . . . ?
O1 S2 C22 F1 -178.3(6) . . . . ?
O3 S2 C22 F1 63.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.083
