# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_250116b
_database_code_depnum_ccdc_archive 'CCDC 2430014'
loop_
_audit_author_name
_audit_author_address
'Min Shao'
;Shanghai University 
China
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-06-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 F2 O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         350.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8190(8)
_cell_length_b                   14.7869(15)
_cell_length_c                   14.7647(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.279(6)
_cell_angle_gamma                90
_cell_volume                     1488.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9208
_cell_measurement_theta_min      4.2320
_cell_measurement_theta_max      66.8173
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720

_exptl_absorpt_coefficient_mu    2.343
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              'Incoatec Ius 3.0'
_diffrn_source_power             0.06
_diffrn_source_current           1.1
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helios MX Multilayer Optic'

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE DUO PHOTON III'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            16460
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_theta_min         4.23
_diffrn_reflns_theta_max         66.96
_diffrn_reflns_theta_full        66.96
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             2595
_reflns_number_gt                2316
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.1209
_refine_ls_wR_factor_gt          0.3603
_refine_ls_wR_factor_ref         0.3626
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_number_reflns         2595
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1940P)²+11.1720P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.518
_refine_diff_density_min         -0.564
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1365)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8140(13) 0.1335(5) 0.4652(6) 0.048(2) Uani d . . . 1 . .
C C2 0.8057(11) 0.2076(5) 0.4076(5) 0.0424(17) Uani d . . . 1 . .
H H2 0.810457 0.200963 0.343682 0.051000 Uiso calc U . R 1 . .
C C3 0.7901(10) 0.2913(5) 0.4480(5) 0.0345(15) Uani d . . . 1 . .
C C4 0.7755(10) 0.3809(5) 0.4025(5) 0.0341(15) Uani d . . . 1 . .
C C5 0.7585(10) 0.4492(5) 0.4775(4) 0.0327(15) Uani d . . . 1 . .
C C6 0.7678(10) 0.3997(5) 0.5679(4) 0.0346(15) Uani d . . . 1 . .
H H6A 0.883002 0.419384 0.604863 0.042000 Uiso calc U . R 1 . .
H H6B 0.647352 0.410313 0.602623 0.042000 Uiso calc U . R 1 . .
C C7 0.7855(10) 0.3012(5) 0.5412(5) 0.0352(15) Uani d . . . 1 . .
C C8 0.7939(12) 0.2251(5) 0.5978(5) 0.0436(17) Uani d . . . 1 . .
H H8 0.789934 0.231261 0.661739 0.052000 Uiso calc U . R 1 . .
C C9 0.8077(13) 0.1423(5) 0.5585(6) 0.0470(19) Uani d . . . 1 . .
H H9 0.813211 0.089802 0.595543 0.056000 Uiso calc U . R 1 . .
C C10 0.7424(10) 0.5374(5) 0.4572(4) 0.0361(16) Uani d . . . 1 . .
H H10 0.739814 0.550885 0.394293 0.043000 Uiso calc U . R 1 . .
C C11 0.7283(10) 0.6157(5) 0.5167(5) 0.0325(14) Uani d . . . 1 . .
C C12 0.7109(10) 0.7015(5) 0.4768(5) 0.0348(15) Uani d . . . 1 . .
H H12 0.708862 0.707149 0.412703 0.042000 Uiso calc U . R 1 . .
C C13 0.6966(10) 0.7779(5) 0.5305(5) 0.0359(15) Uani d . . . 1 . .
H H13 0.685360 0.835801 0.503071 0.043000 Uiso calc U . R 1 . .
C C14 0.6987(10) 0.7703(5) 0.6238(5) 0.0346(15) Uani d . . . 1 . .
C C15 0.7146(11) 0.6847(5) 0.6657(4) 0.0347(15) Uani d . . . 1 . .
C C16 0.7290(11) 0.6082(5) 0.6114(5) 0.0360(15) Uani d . . . 1 . .
H H16 0.739355 0.550199 0.638773 0.043000 Uiso calc U . R 1 . .
C C17 0.730(2) 0.5964(6) 0.7984(5) 0.076(4) Uani d . . . 1 . .
H H17A 0.729776 0.603647 0.864419 0.113000 Uiso calc U . R 1 . .
H H17B 0.850688 0.566079 0.780719 0.113000 Uiso calc U . R 1 . .
H H17C 0.616326 0.559941 0.779058 0.113000 Uiso calc U . R 1 . .
F F1 0.8307(9) 0.0496(3) 0.4291(4) 0.0651(15) Uani d . . . 1 . .
F F2 0.8702(8) 0.8711(3) 0.7435(4) 0.0585(14) Uani d . . . 1 . .
O O1 0.7755(9) 0.3971(4) 0.3223(3) 0.0459(13) Uani d . . . 1 . .
O O2 0.7184(10) 0.6828(4) 0.7566(3) 0.0502(15) Uani d . . . 1 . .
O O3 0.5280(8) 0.8590(4) 0.7531(4) 0.0460(14) Uani d . . . 1 . .
O O4 0.6647(11) 0.9442(4) 0.6293(4) 0.0599(17) Uani d . . . 1 . .
S S1 0.6767(3) 0.86814(12) 0.68813(12) 0.0441(7) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 F1 . 1.356(9) ?
C1 C2 . 1.386(11) ?
C1 C9 . 1.386(13) ?
C2 C3 . 1.380(10) ?
C2 H2 . 0.950000 ?
C3 C7 . 1.386(10) ?
C3 C4 . 1.487(10) ?
C4 O1 . 1.208(9) ?
C4 C5 . 1.506(9) ?
C5 C10 . 1.342(10) ?
C5 C6 . 1.522(9) ?
C6 C7 . 1.514(10) ?
C6 H6A . 0.990000 ?
C6 H6B . 0.990000 ?
C7 C8 . 1.401(10) ?
C8 C9 . 1.359(11) ?
C8 H8 . 0.950000 ?
C9 H9 . 0.950000 ?
C10 C11 . 1.459(10) ?
C10 H10 . 0.950000 ?
C11 C12 . 1.402(10) ?
C11 C16 . 1.402(9) ?
C12 C13 . 1.385(10) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.381(9) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.411(10) ?
C14 S1 . 1.740(7) ?
C15 O2 . 1.342(8) ?
C15 C16 . 1.391(10) ?
C16 H16 . 0.950000 ?
C17 O2 . 1.421(10) ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
F2 S1 . 1.537(6) ?
O3 S1 . 1.417(6) ?
O4 S1 . 1.423(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 C1 C2 . . 119.0(8) ?
F1 C1 C9 . . 118.8(7) ?
C2 C1 C9 . . 122.3(7) ?
C3 C2 C1 . . 116.5(7) ?
C3 C2 H2 . . 121.700000 ?
C1 C2 H2 . . 121.700000 ?
C2 C3 C7 . . 121.9(7) ?
C2 C3 C4 . . 127.5(6) ?
C7 C3 C4 . . 110.6(6) ?
O1 C4 C3 . . 128.2(6) ?
O1 C4 C5 . . 126.1(7) ?
C3 C4 C5 . . 105.7(6) ?
C10 C5 C4 . . 119.6(6) ?
C10 C5 C6 . . 131.6(6) ?
C4 C5 C6 . . 108.7(6) ?
C7 C6 C5 . . 103.6(5) ?
C7 C6 H6A . . 111.000000 ?
C5 C6 H6A . . 111.000000 ?
C7 C6 H6B . . 111.000000 ?
C5 C6 H6B . . 111.000000 ?
H6A C6 H6B . . 109.000000 ?
C3 C7 C8 . . 120.3(7) ?
C3 C7 C6 . . 111.3(6) ?
C8 C7 C6 . . 128.3(6) ?
C9 C8 C7 . . 118.2(7) ?
C9 C8 H8 . . 120.900000 ?
C7 C8 H8 . . 120.900000 ?
C8 C9 C1 . . 120.8(7) ?
C8 C9 H9 . . 119.600000 ?
C1 C9 H9 . . 119.600000 ?
C5 C10 C11 . . 130.0(6) ?
C5 C10 H10 . . 115.000000 ?
C11 C10 H10 . . 115.000000 ?
C12 C11 C16 . . 119.3(6) ?
C12 C11 C10 . . 118.1(6) ?
C16 C11 C10 . . 122.6(6) ?
C13 C12 C11 . . 120.2(6) ?
C13 C12 H12 . . 119.900000 ?
C11 C12 H12 . . 119.900000 ?
C14 C13 C12 . . 120.3(6) ?
C14 C13 H13 . . 119.800000 ?
C12 C13 H13 . . 119.800000 ?
C13 C14 C15 . . 120.6(6) ?
C13 C14 S1 . . 118.5(5) ?
C15 C14 S1 . . 120.9(5) ?
O2 C15 C16 . . 124.0(6) ?
O2 C15 C14 . . 117.2(6) ?
C16 C15 C14 . . 118.8(6) ?
C15 C16 C11 . . 120.7(6) ?
C15 C16 H16 . . 119.600000 ?
C11 C16 H16 . . 119.600000 ?
O2 C17 H17A . . 109.500000 ?
O2 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
O2 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
C15 O2 C17 . . 117.0(6) ?
O3 S1 O4 . . 117.1(4) ?
O3 S1 F2 . . 105.2(3) ?
O4 S1 F2 . . 109.8(4) ?
O3 S1 C14 . . 111.2(3) ?
O4 S1 C14 . . 109.2(3) ?
F2 S1 C14 . . 103.3(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C1 C2 C3 . . . . -179.6(7) ?
C9 C1 C2 C3 . . . . -0.2(12) ?
C1 C2 C3 C7 . . . . 0.8(11) ?
C1 C2 C3 C4 . . . . -178.9(7) ?
C2 C3 C4 O1 . . . . -0.4(13) ?
C7 C3 C4 O1 . . . . 179.8(7) ?
C2 C3 C4 C5 . . . . 179.1(7) ?
C7 C3 C4 C5 . . . . -0.7(8) ?
O1 C4 C5 C10 . . . . -0.4(11) ?
C3 C4 C5 C10 . . . . -179.9(6) ?
O1 C4 C5 C6 . . . . -179.2(7) ?
C3 C4 C5 C6 . . . . 1.3(7) ?
C10 C5 C6 C7 . . . . 180.0(7) ?
C4 C5 C6 C7 . . . . -1.3(7) ?
C2 C3 C7 C8 . . . . -0.9(11) ?
C4 C3 C7 C8 . . . . 178.9(6) ?
C2 C3 C7 C6 . . . . -180.0(6) ?
C4 C3 C7 C6 . . . . -0.2(8) ?
C5 C6 C7 C3 . . . . 1.0(8) ?
C5 C6 C7 C8 . . . . -178.0(7) ?
C3 C7 C8 C9 . . . . 0.4(11) ?
C6 C7 C8 C9 . . . . 179.3(7) ?
C7 C8 C9 C1 . . . . 0.2(13) ?
F1 C1 C9 C8 . . . . 179.1(8) ?
C2 C1 C9 C8 . . . . -0.3(14) ?
C4 C5 C10 C11 . . . . -178.6(7) ?
C6 C5 C10 C11 . . . . 0.0(13) ?
C5 C10 C11 C12 . . . . -179.4(7) ?
C5 C10 C11 C16 . . . . -0.3(12) ?
C16 C11 C12 C13 . . . . 0.7(10) ?
C10 C11 C12 C13 . . . . 179.9(6) ?
C11 C12 C13 C14 . . . . -0.2(11) ?
C12 C13 C14 C15 . . . . -0.2(11) ?
C12 C13 C14 S1 . . . . -179.1(5) ?
C13 C14 C15 O2 . . . . 179.1(7) ?
S1 C14 C15 O2 . . . . -2.1(10) ?
C13 C14 C15 C16 . . . . 0.2(11) ?
S1 C14 C15 C16 . . . . 179.1(6) ?
O2 C15 C16 C11 . . . . -178.6(7) ?
C14 C15 C16 C11 . . . . 0.2(11) ?
C12 C11 C16 C15 . . . . -0.7(11) ?
C10 C11 C16 C15 . . . . -179.8(7) ?
C16 C15 O2 C17 . . . . -2.7(12) ?
C14 C15 O2 C17 . . . . 178.5(8) ?
C13 C14 S1 O3 . . . . 129.2(6) ?
C15 C14 S1 O3 . . . . -49.6(7) ?
C13 C14 S1 O4 . . . . -1.6(7) ?
C15 C14 S1 O4 . . . . 179.6(6) ?
C13 C14 S1 F2 . . . . -118.4(6) ?
C15 C14 S1 F2 . . . . 62.7(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C9 H9 O4 1_545 0.95 2.44 3.266(10) 146.0 ?

