# 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_b240402b_a
_audit_block_doi                 10.5517/ccdc.csd.cc2jqfnc
_database_code_depnum_ccdc_archive 'CCDC 2345263'
loop_
_audit_author_name
_audit_author_address
'Xu Shuilian'
;Soochow University
China
;
_audit_update_record             
;
2024-04-02 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_audit_creation_date             2024-04-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 F3 I N O4 S'
_chemical_formula_sum            'C14 H17 F3 I N O4 S'
_chemical_formula_weight         479.24
_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'
I I -0.4742 1.8119 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6579(6)
_cell_length_b                   10.0811(10)
_cell_length_c                   16.7322(17)
_cell_angle_alpha                73.675(4)
_cell_angle_beta                 83.976(4)
_cell_angle_gamma                86.767(4)
_cell_volume                     910.47(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      27.422
_cell_measurement_theta_min      2.548
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.447
_exptl_absorpt_coefficient_mu    1.919
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27443
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.121
_diffrn_reflns_theta_max         25.121
_diffrn_reflns_theta_min         2.138
_diffrn_ambient_temperature      223.00
_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           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2804
_reflns_number_total             3252
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.567
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       0.0081(9)
_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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.062
_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)+(0.0194P)²+7.5850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1186
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: F2B(0.5) F3B(0.5) F3A(0.5) F2A(0.5)
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C6(H6), C5(H5), C3(H3)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_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
I1 I -0.07978(8) 0.40438(4) 0.67286(3) 0.0483(2) Uani 1 1 d . . . . .
S1 S 0.5470(3) 0.23274(16) 0.44688(10) 0.0370(4) Uani 1 1 d . . . . .
O2 O 0.7170(8) 0.1201(5) 0.4532(3) 0.0452(11) Uani 1 1 d . . . . .
O1 O 0.6211(8) 0.3623(5) 0.4528(3) 0.0478(11) Uani 1 1 d . . . . .
O4 O 0.3750(9) 0.1616(4) 0.7470(3) 0.0475(11) Uani 1 1 d . . . . .
O3 O 0.1307(10) 0.0514(5) 0.6925(3) 0.0571(13) Uani 1 1 d . . . . .
N1 N 0.3341(9) 0.1782(5) 0.5171(3) 0.0427(12) Uani 1 1 d . . . . .
H1 H 0.326562 0.089679 0.540622 0.051 Uiso 1 1 calc R U . . .
C1 C 0.4320(10) 0.2654(6) 0.3489(4) 0.0358(13) Uani 1 1 d . . . . .
F1 F 0.0151(14) 0.4658(7) 0.1010(4) 0.118(2) Uani 1 1 d . . . . .
C9 C 0.2097(11) 0.2889(6) 0.6257(4) 0.0363(13) Uani 1 1 d . . . . .
H9 H 0.358974 0.339895 0.617003 0.044 Uiso 1 1 calc R U . . .
F2B F 0.086(2) 0.2541(13) 0.0920(8) 0.092(4) Uiso 0.5 1 d . . P A 1
C2 C 0.5369(11) 0.3662(7) 0.2818(4) 0.0409(14) Uani 1 1 d . . . . .
H2 H 0.665462 0.415445 0.289102 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2421(11) 0.1929(6) 0.3387(4) 0.0415(14) Uani 1 1 d . . . . .
H6 H 0.172926 0.124251 0.384233 0.050 Uiso 1 1 calc R U . . .
C10 C 0.2324(11) 0.1539(6) 0.6910(4) 0.0375(13) Uani 1 1 d . . . . .
C8 C 0.1518(11) 0.2686(7) 0.5438(4) 0.0415(14) Uani 1 1 d . . . . .
H8A H -0.004329 0.227104 0.551016 0.050 Uiso 1 1 calc R U . . .
H8B H 0.146626 0.358061 0.501329 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1541(12) 0.2220(7) 0.2612(4) 0.0477(16) Uani 1 1 d . . . . .
H5 H 0.023728 0.173987 0.254061 0.057 Uiso 1 1 calc R U . . .
C3 C 0.4511(12) 0.3934(7) 0.2046(4) 0.0462(15) Uani 1 1 d . . . . .
H3 H 0.522740 0.460415 0.158763 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2592(12) 0.3220(7) 0.1944(4) 0.0448(15) Uani 1 1 d . . . . .
F3B F 0.3105(19) 0.3372(12) 0.0532(7) 0.077(3) Uiso 0.5 1 d . . P A 2
C11 C 0.4087(13) 0.0364(7) 0.8116(5) 0.0511(17) Uani 1 1 d . . . . .
H11A H 0.447983 -0.040865 0.787256 0.061 Uiso 1 1 calc R U . . .
H11B H 0.263485 0.015048 0.849637 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6127(14) 0.0592(8) 0.8585(5) 0.060(2) Uani 1 1 d . . . . .
H12A H 0.645810 -0.027221 0.900957 0.072 Uiso 1 1 calc R U . . .
H12B H 0.755184 0.080189 0.818983 0.072 Uiso 1 1 calc R U . . .
C13 C 0.5686(16) 0.1737(9) 0.9009(5) 0.067(2) Uani 1 1 d . . . . .
H13A H 0.532520 0.260303 0.859066 0.080 Uiso 1 1 calc R U . . .
H13B H 0.429738 0.151921 0.942061 0.080 Uiso 1 1 calc R U . . .
C7 C 0.1569(16) 0.3578(9) 0.1124(5) 0.061(2) Uani 1 1 d . . . . .
C14 C 0.7783(19) 0.1936(12) 0.9441(6) 0.090(3) Uani 1 1 d . . . . .
H14A H 0.909774 0.228302 0.902700 0.136 Uiso 1 1 calc R U . . .
H14B H 0.825153 0.105860 0.981452 0.136 Uiso 1 1 calc R U . . .
H14C H 0.735257 0.259530 0.976072 0.136 Uiso 1 1 calc R U . . .
F3A F 0.3182(19) 0.4209(13) 0.0463(7) 0.079(3) Uiso 0.5 1 d . . P A 1
F2A F -0.0277(19) 0.2686(10) 0.1129(6) 0.065(2) Uiso 0.5 1 d . . P A 2


_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
I1 C9 2.166(6) . ?
S1 O2 1.434(4) . ?
S1 O1 1.427(5) . ?
S1 N1 1.596(5) . ?
S1 C1 1.765(6) . ?
O4 C10 1.321(7) . ?
O4 C11 1.430(7) . ?
O3 C10 1.203(7) . ?
N1 H1 0.8700 . ?
N1 C8 1.457(8) . ?
C1 C2 1.390(8) . ?
C1 C6 1.383(9) . ?
F1 C7 1.297(10) . ?
C9 H9 0.9900 . ?
C9 C10 1.495(8) . ?
C9 C8 1.511(9) . ?
F2B C7 1.283(14) . ?
C2 H2 0.9400 . ?
C2 C3 1.378(9) . ?
C6 H6 0.9400 . ?
C6 C5 1.386(9) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C5 H5 0.9400 . ?
C5 C4 1.384(10) . ?
C3 H3 0.9400 . ?
C3 C4 1.386(9) . ?
C4 C7 1.488(10) . ?
F3B C7 1.301(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C12 1.524(11) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 C13 1.514(11) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 C14 1.503(12) . ?
C7 F3A 1.385(14) . ?
C7 F2A 1.414(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?

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 106.5(3) . . ?
O2 S1 C1 107.3(3) . . ?
O1 S1 O2 119.4(3) . . ?
O1 S1 N1 109.3(3) . . ?
O1 S1 C1 106.6(3) . . ?
N1 S1 C1 107.3(3) . . ?
C10 O4 C11 115.5(5) . . ?
S1 N1 H1 118.2 . . ?
C8 N1 S1 123.6(4) . . ?
C8 N1 H1 118.2 . . ?
C2 C1 S1 118.3(5) . . ?
C6 C1 S1 121.1(5) . . ?
C6 C1 C2 120.6(6) . . ?
I1 C9 H9 109.9 . . ?
C10 C9 I1 106.5(4) . . ?
C10 C9 H9 109.9 . . ?
C10 C9 C8 111.6(5) . . ?
C8 C9 I1 109.1(4) . . ?
C8 C9 H9 109.9 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(6) . . ?
C3 C2 H2 120.3 . . ?
C1 C6 H6 120.1 . . ?
C1 C6 C5 119.7(6) . . ?
C5 C6 H6 120.1 . . ?
O4 C10 C9 111.7(5) . . ?
O3 C10 O4 124.3(6) . . ?
O3 C10 C9 123.9(6) . . ?
N1 C8 C9 108.8(5) . . ?
N1 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(6) . . ?
C4 C5 H5 120.2 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(6) . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.5(6) . . ?
C5 C4 C7 119.4(7) . . ?
C3 C4 C7 120.0(7) . . ?
O4 C11 H11A 110.3 . . ?
O4 C11 H11B 110.3 . . ?
O4 C11 C12 106.9(6) . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 C11 115.0(7) . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.4(8) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
F1 C7 C4 113.0(7) . . ?
F1 C7 F3B 122.1(9) . . ?
F1 C7 F3A 93.1(8) . . ?
F1 C7 F2A 93.0(8) . . ?
F2B C7 F1 116.4(10) . . ?
F2B C7 C4 114.7(9) . . ?
F2B C7 F3A 104.5(10) . . ?
F3B C7 C4 111.8(8) . . ?
F3B C7 F2A 102.6(9) . . ?
F3A C7 C4 112.7(8) . . ?
F2A C7 C4 111.6(7) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
I1 C9 C10 O4 -88.1(5) . . . . ?
I1 C9 C10 O3 91.2(7) . . . . ?
I1 C9 C8 N1 -173.8(4) . . . . ?
S1 N1 C8 C9 -101.2(6) . . . . ?
S1 C1 C2 C3 179.8(5) . . . . ?
S1 C1 C6 C5 179.3(5) . . . . ?
O2 S1 N1 C8 166.0(5) . . . . ?
O2 S1 C1 C2 -94.2(5) . . . . ?
O2 S1 C1 C6 85.9(5) . . . . ?
O1 S1 N1 C8 35.7(6) . . . . ?
O1 S1 C1 C2 34.8(6) . . . . ?
O1 S1 C1 C6 -145.1(5) . . . . ?
O4 C11 C12 C13 61.7(8) . . . . ?
N1 S1 C1 C2 151.8(5) . . . . ?
N1 S1 C1 C6 -28.1(6) . . . . ?
C1 S1 N1 C8 -79.4(6) . . . . ?
C1 C2 C3 C4 1.0(10) . . . . ?
C1 C6 C5 C4 0.8(10) . . . . ?
C2 C1 C6 C5 -0.6(9) . . . . ?
C2 C3 C4 C5 -0.8(10) . . . . ?
C2 C3 C4 C7 176.1(7) . . . . ?
C6 C1 C2 C3 -0.3(9) . . . . ?
C6 C5 C4 C3 -0.1(10) . . . . ?
C6 C5 C4 C7 -177.0(6) . . . . ?
C10 O4 C11 C12 169.1(6) . . . . ?
C10 C9 C8 N1 -56.5(7) . . . . ?
C8 C9 C10 O4 153.0(5) . . . . ?
C8 C9 C10 O3 -27.7(9) . . . . ?
C5 C4 C7 F1 96.7(9) . . . . ?
C5 C4 C7 F2B -40.0(12) . . . . ?
C5 C4 C7 F3B -121.0(9) . . . . ?
C5 C4 C7 F3A -159.4(8) . . . . ?
C5 C4 C7 F2A -6.6(11) . . . . ?
C3 C4 C7 F1 -80.2(10) . . . . ?
C3 C4 C7 F2B 143.2(10) . . . . ?
C3 C4 C7 F3B 62.2(11) . . . . ?
C3 C4 C7 F3A 23.8(11) . . . . ?
C3 C4 C7 F2A 176.5(7) . . . . ?
C11 O4 C10 O3 1.3(10) . . . . ?
C11 O4 C10 C9 -179.4(5) . . . . ?
C11 C12 C13 C14 -178.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
