# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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. 
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data_251120b1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2504930'
loop_
_audit_author_name
_audit_author_address
'zhang xiaoke'
;Zunyi Medical University
China
;
_audit_update_record             
;
2025-11-23 deposited with the CCDC.	2026-05-04 downloaded from the CCDC.
;
_audit_creation_date             2025-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 F3 N2 O2 S'
_chemical_formula_sum            'C18 H17 F3 N2 O2 S'
_chemical_formula_weight         382.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   13.219(4)
_cell_length_b                   5.4793(17)
_cell_length_c                   24.982(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.975(14)
_cell_angle_gamma                90
_cell_volume                     1782.1(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3768
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5050
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1355 before and 0.0995 after correction.
The Ratio of minimum to maximum transmission is 0.6773.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1274
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19156
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.696
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1859
_reflns_number_total             3639
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3639
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+2.1523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1548
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15),
  C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.57678(9) 0.36861(19) 0.39874(5) 0.0604(3) Uani 1 1 d . . . . .
F1 F 0.9535(2) 0.7631(5) 0.48054(13) 0.0942(9) Uani 1 1 d . . . . .
F2 F 0.9405(2) 0.7047(6) 0.39467(13) 0.0983(10) Uani 1 1 d . . . . .
F3 F 0.8870(2) 1.0401(5) 0.42400(12) 0.0930(9) Uani 1 1 d . . . . .
O1 O 0.6465(2) 0.3007(5) 0.44702(13) 0.0725(9) Uani 1 1 d . . . . .
O2 O 0.5207(2) 0.1808(5) 0.36670(13) 0.0758(9) Uani 1 1 d . . . . .
N1 N 0.6453(3) 0.5142(6) 0.35849(14) 0.0551(9) Uani 1 1 d . . . . .
N2 N 0.7359(3) 0.7968(6) 0.47184(14) 0.0647(10) Uani 1 1 d . . . . .
H2 H 0.692458 0.910626 0.460922 0.078 Uiso 1 1 calc R U . . .
C1 C 0.7227(3) 0.6929(7) 0.37622(18) 0.0551(11) Uani 1 1 d . . . . .
C2 C 0.7271(3) 0.8453(8) 0.33450(18) 0.0611(11) Uani 1 1 d . . . . .
H2A H 0.772302 0.975820 0.335290 0.073 Uiso 1 1 calc R U . . .
C3 C 0.6517(3) 0.7761(7) 0.28857(18) 0.0576(11) Uani 1 1 d . . . . .
C4 C 0.6262(4) 0.8678(9) 0.23568(19) 0.0717(13) Uani 1 1 d . . . . .
H4 H 0.660365 1.002704 0.224959 0.086 Uiso 1 1 calc R U . . .
C5 C 0.5501(4) 0.7559(10) 0.2000(2) 0.0793(15) Uani 1 1 d . . . . .
H5 H 0.531255 0.816737 0.164942 0.095 Uiso 1 1 calc R U . . .
C6 C 0.5016(4) 0.5534(10) 0.2160(2) 0.0825(15) Uani 1 1 d . . . . .
H6 H 0.450910 0.478705 0.190859 0.099 Uiso 1 1 calc R U . . .
C7 C 0.5248(4) 0.4562(9) 0.2675(2) 0.0764(14) Uani 1 1 d . . . . .
H7 H 0.490724 0.319745 0.277564 0.092 Uiso 1 1 calc R U . . .
C8 C 0.6015(3) 0.5715(7) 0.30361(18) 0.0586(11) Uani 1 1 d . . . . .
C9 C 0.7873(3) 0.6842(7) 0.43189(17) 0.0558(11) Uani 1 1 d . . . . .
H9 H 0.798289 0.512095 0.441900 0.067 Uiso 1 1 calc R U . . .
C10 C 0.8927(4) 0.8000(9) 0.4326(2) 0.0728(13) Uani 1 1 d . . . . .
C11 C 0.7512(3) 0.7357(7) 0.52693(17) 0.0526(10) Uani 1 1 d . . . . .
C12 C 0.8027(4) 0.5265(8) 0.54850(19) 0.0667(13) Uani 1 1 d . . . . .
H12 H 0.832538 0.423055 0.526152 0.080 Uiso 1 1 calc R U . . .
C13 C 0.8094(4) 0.4726(8) 0.60273(19) 0.0679(13) Uani 1 1 d . . . . .
H13 H 0.843108 0.330240 0.615973 0.081 Uiso 1 1 calc R U . . .
C14 C 0.7688(4) 0.6188(9) 0.63827(19) 0.0672(13) Uani 1 1 d . . . . .
C15 C 0.7196(4) 0.8301(9) 0.6167(2) 0.0719(14) Uani 1 1 d . . . . .
H15 H 0.691936 0.935988 0.639440 0.086 Uiso 1 1 calc R U . . .
C16 C 0.7109(3) 0.8857(8) 0.56227(19) 0.0635(12) Uani 1 1 d . . . . .
H16 H 0.677151 1.027990 0.549070 0.076 Uiso 1 1 calc R U . . .
C17 C 0.7756(5) 0.5505(10) 0.6979(2) 0.0973(18) Uani 1 1 d . . . . .
H17A H 0.775095 0.376094 0.701393 0.146 Uiso 1 1 calc R U . . .
H17B H 0.717974 0.618148 0.711427 0.146 Uiso 1 1 calc R U . . .
H17C H 0.838132 0.614379 0.718449 0.146 Uiso 1 1 calc R U . . .
C18 C 0.4922(3) 0.5890(7) 0.41551(19) 0.0695(13) Uani 1 1 d . . . . .
H18A H 0.446429 0.515342 0.436751 0.104 Uiso 1 1 calc R U . . .
H18B H 0.453171 0.656089 0.382848 0.104 Uiso 1 1 calc R U . . .
H18C H 0.530492 0.716674 0.436169 0.104 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.435(3) . ?
S1 O2 1.429(3) . ?
S1 N1 1.669(3) . ?
S1 C18 1.745(4) . ?
F1 C10 1.338(5) . ?
F2 C10 1.332(5) . ?
F3 C10 1.333(5) . ?
N1 C1 1.430(5) . ?
N1 C8 1.427(5) . ?
N2 H2 0.8600 . ?
N2 C9 1.439(5) . ?
N2 C11 1.397(5) . ?
C1 C2 1.345(5) . ?
C1 C9 1.502(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.435(6) . ?
C3 C4 1.399(6) . ?
C3 C8 1.387(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(6) . ?
C9 H9 0.9800 . ?
C9 C10 1.528(6) . ?
C11 C12 1.393(6) . ?
C11 C16 1.379(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(6) . ?
C14 C15 1.390(6) . ?
C14 C17 1.523(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(6) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 107.08(19) . . ?
O1 S1 C18 108.8(2) . . ?
O2 S1 O1 118.64(19) . . ?
O2 S1 N1 106.84(19) . . ?
O2 S1 C18 109.9(2) . . ?
N1 S1 C18 104.56(19) . . ?
C1 N1 S1 125.1(3) . . ?
C8 N1 S1 120.8(3) . . ?
C8 N1 C1 107.2(3) . . ?
C9 N2 H2 117.4 . . ?
C11 N2 H2 117.4 . . ?
C11 N2 C9 125.1(3) . . ?
N1 C1 C9 121.8(4) . . ?
C2 C1 N1 108.1(4) . . ?
C2 C1 C9 130.1(4) . . ?
C1 C2 H2A 125.1 . . ?
C1 C2 C3 109.8(4) . . ?
C3 C2 H2A 125.1 . . ?
C4 C3 C2 132.9(4) . . ?
C8 C3 C2 107.2(4) . . ?
C8 C3 C4 119.9(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(5) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 118.5 . . ?
C5 C6 C7 122.9(5) . . ?
C7 C6 H6 118.5 . . ?
C6 C7 H7 121.6 . . ?
C6 C7 C8 116.8(5) . . ?
C8 C7 H7 121.6 . . ?
C3 C8 N1 107.7(4) . . ?
C3 C8 C7 121.4(4) . . ?
C7 C8 N1 130.8(4) . . ?
N2 C9 C1 111.6(3) . . ?
N2 C9 H9 107.6 . . ?
N2 C9 C10 110.7(4) . . ?
C1 C9 H9 107.6 . . ?
C1 C9 C10 111.6(4) . . ?
C10 C9 H9 107.6 . . ?
F1 C10 C9 110.6(4) . . ?
F2 C10 F1 107.0(4) . . ?
F2 C10 F3 107.1(4) . . ?
F2 C10 C9 111.9(4) . . ?
F3 C10 F1 107.6(4) . . ?
F3 C10 C9 112.4(4) . . ?
C12 C11 N2 123.8(4) . . ?
C16 C11 N2 118.8(4) . . ?
C16 C11 C12 117.4(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 118.4 . . ?
C14 C13 C12 123.1(4) . . ?
C14 C13 H13 118.4 . . ?
C13 C14 C15 116.4(4) . . ?
C13 C14 C17 121.7(5) . . ?
C15 C14 C17 121.9(5) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.3(4) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C15 121.6(4) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
S1 N1 C1 C2 -152.0(3) . . . . ?
S1 N1 C1 C9 31.2(5) . . . . ?
S1 N1 C8 C3 152.9(3) . . . . ?
S1 N1 C8 C7 -28.4(6) . . . . ?
O1 S1 N1 C1 -43.0(4) . . . . ?
O1 S1 N1 C8 170.0(3) . . . . ?
O2 S1 N1 C1 -171.1(3) . . . . ?
O2 S1 N1 C8 41.9(3) . . . . ?
N1 C1 C2 C3 1.4(5) . . . . ?
N1 C1 C9 N2 -84.0(4) . . . . ?
N1 C1 C9 C10 151.6(4) . . . . ?
N2 C9 C10 F1 62.9(5) . . . . ?
N2 C9 C10 F2 -177.9(4) . . . . ?
N2 C9 C10 F3 -57.3(5) . . . . ?
N2 C11 C12 C13 -176.4(4) . . . . ?
N2 C11 C16 C15 177.2(4) . . . . ?
C1 N1 C8 C3 0.7(4) . . . . ?
C1 N1 C8 C7 179.4(5) . . . . ?
C1 C2 C3 C4 -178.2(4) . . . . ?
C1 C2 C3 C8 -1.0(5) . . . . ?
C1 C9 C10 F1 -172.2(4) . . . . ?
C1 C9 C10 F2 -53.0(5) . . . . ?
C1 C9 C10 F3 67.6(5) . . . . ?
C2 C1 C9 N2 100.0(5) . . . . ?
C2 C1 C9 C10 -24.3(6) . . . . ?
C2 C3 C4 C5 178.4(5) . . . . ?
C2 C3 C8 N1 0.1(4) . . . . ?
C2 C3 C8 C7 -178.7(4) . . . . ?
C3 C4 C5 C6 -1.4(7) . . . . ?
C4 C3 C8 N1 177.8(4) . . . . ?
C4 C3 C8 C7 -1.0(6) . . . . ?
C4 C5 C6 C7 1.0(8) . . . . ?
C5 C6 C7 C8 -0.5(7) . . . . ?
C6 C7 C8 N1 -178.0(4) . . . . ?
C6 C7 C8 C3 0.6(7) . . . . ?
C8 N1 C1 C2 -1.3(4) . . . . ?
C8 N1 C1 C9 -178.0(4) . . . . ?
C8 C3 C4 C5 1.4(6) . . . . ?
C9 N2 C11 C12 -13.2(7) . . . . ?
C9 N2 C11 C16 168.7(4) . . . . ?
C9 C1 C2 C3 177.8(4) . . . . ?
C11 N2 C9 C1 151.8(4) . . . . ?
C11 N2 C9 C10 -83.2(5) . . . . ?
C11 C12 C13 C14 -1.2(7) . . . . ?
C12 C11 C16 C15 -1.0(6) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C12 C13 C14 C17 178.6(5) . . . . ?
C13 C14 C15 C16 1.1(7) . . . . ?
C14 C15 C16 C11 -0.4(7) . . . . ?
C16 C11 C12 C13 1.8(7) . . . . ?
C17 C14 C15 C16 -177.8(4) . . . . ?
C18 S1 N1 C1 72.4(4) . . . . ?
C18 S1 N1 C8 -74.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
