# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_BTP4CF3_0m
_database_code_depnum_ccdc_archive 'CCDC 2297186'
loop_
_audit_author_name
_audit_author_address
'Sammer Yousuf'
;University of Karachi
Pakistan
;
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2024-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H9 F3 O2 S'
_chemical_formula_weight         322.29

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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 '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                   6.5671(10)
_cell_length_b                   7.2171(11)
_cell_length_c                   14.364(2)
_cell_angle_alpha                85.588(4)
_cell_angle_beta                 81.019(4)
_cell_angle_gamma                83.178(4)
_cell_volume                     666.48(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9864
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      68.59

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorles
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   0.5140
_exptl_transmission_factor_max   0.7840
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.556
_shelx_estimated_absorpt_T_min   0.514
_shelx_estimated_absorpt_T_max   0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            15239
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         68.185
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2413
_reflns_number_gt                2363
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0746P)²+0.3694P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2413
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_restrained_S_all      1.275
_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 0.33058(7) 0.82846(6) 0.50569(3) 0.0150(2) Uani 1 1 d . . . . .
F1 F 0.5620(2) 0.7864(3) -0.02983(10) 0.0379(4) Uani 1 1 d . . . . .
O1 O -0.2293(2) 0.6803(2) 0.56561(11) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.2415(3) 0.8169(3) 0.62643(14) 0.0157(4) Uani 1 1 d . . . . .
H1 H -0.247(5) 0.675(5) 0.505(3) 0.041(9) Uiso 1 1 d . . . . .
F2 F 0.7319(3) 0.5475(2) 0.02860(11) 0.0436(5) Uani 1 1 d . . . . .
O2 O -0.1284(2) 0.6916(2) 0.38272(10) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.3495(3) 0.8527(3) 0.69818(15) 0.0191(5) Uani 1 1 d . . . . .
H2 H 0.483103 0.894952 0.683910 0.023 Uiso 1 1 calc R U . . .
F3 F 0.7971(2) 0.8217(3) 0.05208(10) 0.0398(4) Uani 1 1 d . . . . .
C3 C 0.2566(4) 0.8252(3) 0.79068(16) 0.0228(5) Uani 1 1 d . . . . .
H3 H 0.328484 0.847902 0.840434 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0585(4) 0.7643(3) 0.81282(15) 0.0235(5) Uani 1 1 d . . . . .
H4 H -0.000296 0.744654 0.877063 0.028 Uiso 1 1 calc R U . . .
C5 C -0.0517(3) 0.7328(3) 0.74236(15) 0.0194(5) Uani 1 1 d . . . . .
H5 H -0.186745 0.693838 0.757337 0.023 Uiso 1 1 calc R U . . .
C6 C 0.0408(3) 0.7598(3) 0.64749(14) 0.0151(4) Uani 1 1 d . . . . .
C7 C -0.0392(3) 0.7315(3) 0.56298(15) 0.0141(4) Uani 1 1 d . . . . .
C8 C 0.0995(3) 0.7575(3) 0.48126(15) 0.0137(4) Uani 1 1 d . . . . .
C9 C 0.0502(3) 0.7239(3) 0.38933(14) 0.0140(4) Uani 1 1 d . . . . .
C10 C 0.2092(3) 0.7240(3) 0.30234(14) 0.0141(4) Uani 1 1 d . . . . .
C11 C 0.1405(3) 0.7803(3) 0.21630(15) 0.0175(4) Uani 1 1 d . . . . .
H11 H -0.002429 0.818904 0.214845 0.021 Uiso 1 1 calc R U . . .
C12 C 0.2793(3) 0.7804(3) 0.13291(15) 0.0191(5) Uani 1 1 d . . . . .
H12 H 0.232696 0.821315 0.074617 0.023 Uiso 1 1 calc R U . . .
C13 C 0.4879(3) 0.7199(3) 0.13566(15) 0.0167(4) Uani 1 1 d . . . . .
C14 C 0.5574(3) 0.6603(3) 0.22066(15) 0.0167(4) Uani 1 1 d . . . . .
H14 H 0.699749 0.618106 0.221764 0.020 Uiso 1 1 calc R U . . .
C15 C 0.4181(3) 0.6626(3) 0.30395(14) 0.0150(4) Uani 1 1 d . . . . .
H15 H 0.465188 0.622229 0.362196 0.018 Uiso 1 1 calc R U . . .
C16 C 0.6425(3) 0.7184(3) 0.04689(15) 0.0208(5) 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
S1 C1 1.740(2) . ?
S1 C8 1.751(2) . ?
F1 C16 1.331(3) . ?
O1 C7 1.337(2) . ?
O1 H1 0.89(4) . ?
C1 C2 1.395(3) . ?
C1 C6 1.408(3) . ?
F2 C16 1.328(3) . ?
O2 C9 1.242(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
F3 C16 1.344(3) . ?
C3 C4 1.404(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.433(3) . ?
C7 C8 1.384(3) . ?
C8 C9 1.452(3) . ?
C9 C10 1.498(3) . ?
C10 C15 1.393(3) . ?
C10 C11 1.396(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 C16 1.501(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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 C8 91.36(10) . . ?
C7 O1 H1 106(2) . . ?
C2 C1 C6 120.94(19) . . ?
C2 C1 S1 126.73(17) . . ?
C6 C1 S1 112.31(16) . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 120.09(19) . . ?
C1 C6 C7 111.09(18) . . ?
C5 C6 C7 128.79(19) . . ?
O1 C7 C8 124.58(19) . . ?
O1 C7 C6 121.69(18) . . ?
C8 C7 C6 113.72(18) . . ?
C7 C8 C9 121.50(18) . . ?
C7 C8 S1 111.46(15) . . ?
C9 C8 S1 127.03(15) . . ?
O2 C9 C8 119.08(18) . . ?
O2 C9 C10 118.93(18) . . ?
C8 C9 C10 121.98(17) . . ?
C15 C10 C11 119.60(19) . . ?
C15 C10 C9 122.69(18) . . ?
C11 C10 C9 117.65(18) . . ?
C12 C11 C10 120.54(19) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.22(19) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.75(19) . . ?
C14 C13 C16 118.55(19) . . ?
C12 C13 C16 120.70(19) . . ?
C15 C14 C13 119.70(19) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 120.17(19) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
F2 C16 F1 106.41(19) . . ?
F2 C16 F3 106.18(19) . . ?
F1 C16 F3 105.61(18) . . ?
F2 C16 C13 112.36(18) . . ?
F1 C16 C13 113.79(18) . . ?
F3 C16 C13 111.91(17) . . ?

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
C8 S1 C1 C2 178.46(19) . . . . ?
C8 S1 C1 C6 0.16(15) . . . . ?
C6 C1 C2 C3 2.0(3) . . . . ?
S1 C1 C2 C3 -176.20(16) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
S1 C1 C6 C5 176.54(15) . . . . ?
C2 C1 C6 C7 179.95(17) . . . . ?
S1 C1 C6 C7 -1.6(2) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 178.10(19) . . . . ?
C1 C6 C7 O1 -178.72(16) . . . . ?
C5 C6 C7 O1 3.3(3) . . . . ?
C1 C6 C7 C8 2.8(2) . . . . ?
C5 C6 C7 C8 -175.21(19) . . . . ?
O1 C7 C8 C9 -2.2(3) . . . . ?
C6 C7 C8 C9 176.24(17) . . . . ?
O1 C7 C8 S1 178.89(15) . . . . ?
C6 C7 C8 S1 -2.6(2) . . . . ?
C1 S1 C8 C7 1.42(15) . . . . ?
C1 S1 C8 C9 -177.39(18) . . . . ?
C7 C8 C9 O2 8.2(3) . . . . ?
S1 C8 C9 O2 -173.06(14) . . . . ?
C7 C8 C9 C10 -170.80(17) . . . . ?
S1 C8 C9 C10 7.9(3) . . . . ?
O2 C9 C10 C15 -145.7(2) . . . . ?
C8 C9 C10 C15 33.3(3) . . . . ?
O2 C9 C10 C11 31.3(3) . . . . ?
C8 C9 C10 C11 -149.71(19) . . . . ?
C15 C10 C11 C12 -1.8(3) . . . . ?
C9 C10 C11 C12 -178.85(18) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C11 C12 C13 C16 -179.93(19) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C16 C13 C14 C15 179.19(18) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
C9 C10 C15 C14 177.95(17) . . . . ?
C14 C13 C16 F2 62.0(3) . . . . ?
C12 C13 C16 F2 -118.2(2) . . . . ?
C14 C13 C16 F1 -176.94(19) . . . . ?
C12 C13 C16 F1 2.9(3) . . . . ?
C14 C13 C16 F3 -57.3(3) . . . . ?
C12 C13 C16 F3 122.5(2) . . . . ?

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
O1 H1 O2 0.89(4) 1.81(4) 2.604(2) 146(3) .

_refine_diff_density_max         0.497
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.154



