# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_bixh230913_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2296818'
loop_
_audit_author_name
_audit_author_address
yy
;nenu
China
;
_audit_update_record             
;
2023-09-22 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 F3 N2 O2 S'
_chemical_formula_sum            'C10 H9 F3 N2 O2 S'
_chemical_formula_weight         278.25
_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 0.0181 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'
N N 0.0311 0.0180 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.146(5)
_cell_length_b                   8.147(2)
_cell_length_c                   16.078(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.284(13)
_cell_angle_gamma                90
_cell_volume                     2461.8(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4168
_cell_measurement_temperature    270.17
_cell_measurement_theta_max      63.42
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.705
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.3676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1503 before and 0.0840 after correction.
The Ratio of minimum to maximum transmission is 0.4886.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5712
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        63.719
_diffrn_reflns_theta_max         63.719
_diffrn_reflns_theta_min         5.813
_diffrn_ambient_temperature      270.17
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_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                1576
_reflns_number_total             1944
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+2.9177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1412
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.58517(4) 0.06352(10) 0.44352(6) 0.0588(4) Uani 1 1 d . . . . .
F1 F 0.42471(10) 0.2667(3) 0.31093(14) 0.0821(7) Uani 1 1 d . . . . .
F2 F 0.43067(12) 0.4974(3) 0.37670(19) 0.0964(8) Uani 1 1 d . . . . .
F3 F 0.47006(10) 0.2822(3) 0.46013(13) 0.0762(6) Uani 1 1 d . . . . .
C1 C 0.7667(3) 0.1593(7) 0.8636(3) 0.0911(14) Uani 1 1 d . . . . .
O2 O 0.64128(14) -0.0226(3) 0.4364(2) 0.0824(8) Uani 1 1 d . . . . .
O3 O 0.51435(12) 0.0028(3) 0.39473(16) 0.0689(7) Uani 1 1 d . . . . .
N1 N 0.60173(14) 0.0653(4) 0.55224(18) 0.0679(8) Uani 1 1 d . . . . .
H1 H 0.570337 0.034411 0.568954 0.082 Uiso 1 1 calc R U . . .
N2 N 0.66832(13) 0.1183(4) 0.6173(2) 0.0629(7) Uani 1 1 d . . . . .
C10 C 0.6167(2) 0.5864(5) 0.3723(3) 0.0715(10) Uani 1 1 d . . . . .
H10 H 0.625011 0.692539 0.358400 0.086 Uiso 1 1 calc R U . . .
C2 C 0.6677(2) 0.4693(5) 0.3944(3) 0.0690(10) Uani 1 1 d . . . . .
H2 H 0.711272 0.495827 0.396804 0.083 Uiso 1 1 calc R U . . .
C3 C 0.65503(16) 0.3127(4) 0.4132(2) 0.0600(9) Uani 1 1 d . . . . .
H3 H 0.689867 0.232913 0.426827 0.072 Uiso 1 1 calc R U . . .
C4 C 0.59093(14) 0.2702(4) 0.41216(19) 0.0495(7) Uani 1 1 d . . . . .
C5 C 0.68034(16) 0.1169(4) 0.7024(2) 0.0602(8) Uani 1 1 d . . . . .
H5 H 0.645022 0.083344 0.717910 0.072 Uiso 1 1 calc R U . . .
C6 C 0.74844(18) 0.1672(5) 0.7743(3) 0.0765(11) Uani 1 1 d . . . . .
H6 H 0.781487 0.207691 0.756377 0.092 Uiso 1 1 calc R U . . .
C7 C 0.55205(19) 0.5474(4) 0.3706(2) 0.0635(9) Uani 1 1 d . . . . .
H7 H 0.517727 0.628590 0.356548 0.076 Uiso 1 1 calc R U . . .
C8 C 0.53817(15) 0.3906(4) 0.38942(19) 0.0504(7) Uani 1 1 d . . . . .
C9 C 0.46610(18) 0.3578(5) 0.3840(2) 0.0651(9) Uani 1 1 d . . . . .
H1A H 0.731(2) 0.116(6) 0.881(3) 0.097(13) Uiso 1 1 d . . . . .
H1B H 0.811(3) 0.186(6) 0.910(4) 0.104(15) Uiso 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 O2 1.427(2) . ?
S1 O3 1.423(2) . ?
S1 N1 1.618(3) . ?
S1 C4 1.778(3) . ?
F1 C9 1.324(4) . ?
F2 C9 1.337(4) . ?
F3 C9 1.339(4) . ?
C1 C6 1.306(6) . ?
C1 H1A 0.98(5) . ?
C1 H1B 0.92(5) . ?
N1 H1 0.8600 . ?
N1 N2 1.383(4) . ?
N2 C5 1.273(4) . ?
C10 H10 0.9300 . ?
C10 C2 1.360(5) . ?
C10 C7 1.391(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(4) . ?
C4 C8 1.403(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.432(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.375(5) . ?
C8 C9 1.510(4) . ?

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
O2 S1 N1 108.34(17) . . ?
O2 S1 C4 105.96(14) . . ?
O3 S1 O2 119.24(16) . . ?
O3 S1 N1 104.51(14) . . ?
O3 S1 C4 111.37(14) . . ?
N1 S1 C4 106.80(15) . . ?
C6 C1 H1A 117(3) . . ?
C6 C1 H1B 124(3) . . ?
H1A C1 H1B 119(4) . . ?
S1 N1 H1 121.3 . . ?
N2 N1 S1 117.4(2) . . ?
N2 N1 H1 121.3 . . ?
C5 N2 N1 116.3(3) . . ?
C2 C10 H10 120.0 . . ?
C2 C10 C7 120.0(3) . . ?
C7 C10 H10 120.0 . . ?
C10 C2 H2 120.0 . . ?
C10 C2 C3 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 S1 115.2(2) . . ?
C3 C4 C8 118.9(3) . . ?
C8 C4 S1 125.9(2) . . ?
N2 C5 H5 120.1 . . ?
N2 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 123.7(4) . . ?
C1 C6 H6 118.2 . . ?
C5 C6 H6 118.2 . . ?
C10 C7 H7 119.5 . . ?
C8 C7 C10 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C4 C8 C9 123.5(3) . . ?
C7 C8 C4 118.9(3) . . ?
C7 C8 C9 117.6(3) . . ?
F1 C9 F2 106.4(3) . . ?
F1 C9 F3 107.0(3) . . ?
F1 C9 C8 113.0(3) . . ?
F2 C9 F3 105.6(3) . . ?
F2 C9 C8 111.4(3) . . ?
F3 C9 C8 113.0(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
_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 N2 C5 -179.3(3) . . . . ?
S1 C4 C8 C7 177.1(2) . . . . ?
S1 C4 C8 C9 -3.1(4) . . . . ?
O2 S1 N1 N2 51.3(3) . . . . ?
O2 S1 C4 C3 -16.4(3) . . . . ?
O2 S1 C4 C8 165.2(3) . . . . ?
O3 S1 N1 N2 179.4(2) . . . . ?
O3 S1 C4 C3 -147.5(2) . . . . ?
O3 S1 C4 C8 34.1(3) . . . . ?
N1 S1 C4 C3 99.0(2) . . . . ?
N1 S1 C4 C8 -79.5(3) . . . . ?
N1 N2 C5 C6 178.9(3) . . . . ?
N2 C5 C6 C1 -175.4(4) . . . . ?
C10 C2 C3 C4 -1.4(5) . . . . ?
C10 C7 C8 C4 1.1(5) . . . . ?
C10 C7 C8 C9 -178.7(3) . . . . ?
C2 C10 C7 C8 -1.1(5) . . . . ?
C2 C3 C4 S1 -177.2(3) . . . . ?
C2 C3 C4 C8 1.4(5) . . . . ?
C3 C4 C8 C7 -1.2(4) . . . . ?
C3 C4 C8 C9 178.5(3) . . . . ?
C4 S1 N1 N2 -62.5(3) . . . . ?
C4 C8 C9 F1 -70.7(4) . . . . ?
C4 C8 C9 F2 169.5(3) . . . . ?
C4 C8 C9 F3 50.8(4) . . . . ?
C7 C10 C2 C3 1.3(5) . . . . ?
C7 C8 C9 F1 109.0(3) . . . . ?
C7 C8 C9 F2 -10.7(4) . . . . ?
C7 C8 C9 F3 -129.4(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
