# Supplementary Information (SI) for Chemical Science.
# 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. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2501744'
loop_
_audit_author_name
_audit_author_address
'Seishu Ochiai'
;Department of Life Science and Applied Chemistry, Nagoya Institute of Technology
Japan
;
_audit_update_record             
;
2025-11-10 deposited with the CCDC.	2026-03-20 downloaded from the CCDC.
;
_audit_creation_date             2025-11-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 F5 N2 S'
_chemical_formula_sum            'C15 H15 F5 N2 S'
_chemical_formula_weight         350.35
_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'
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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   28.614(3)
_cell_length_b                   8.9784(10)
_cell_length_c                   11.6868(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3002.4(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12290
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      1.88
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chip
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1431
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24268
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.378
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1871
_reflns_number_total             3270
_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       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2000)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0820
_refine_ls_restrained_S_all      1.094
_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)+(0.1672P)²+0.5502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2374
_refine_ls_wR_factor_ref         0.3160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C2(H2A,H2B), C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C14(H14), C7(H7), C4(H4), C6(H6), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.43770(5) 0.84906(13) 0.61347(9) 0.0613(5) Uani 1 1 d . . . . .
F1 F 0.45278(11) 0.7384(3) 0.7114(2) 0.0736(9) Uani 1 1 d . . . . .
F4 F 0.49107(10) 0.8929(3) 0.5941(2) 0.0697(8) Uani 1 1 d . . . . .
F2 F 0.38318(10) 0.8159(3) 0.6407(2) 0.0759(9) Uani 1 1 d . . . . .
F3 F 0.42222(12) 0.9737(3) 0.5262(2) 0.0752(9) Uani 1 1 d . . . . .
F5 F 0.43569(12) 0.9743(3) 0.7090(2) 0.0827(10) Uani 1 1 d . . . . .
N1 N 0.35740(14) 0.4006(4) 0.3609(3) 0.0593(10) Uani 1 1 d . . . . .
N2 N 0.40397(14) 0.5811(4) 0.2841(3) 0.0556(10) Uani 1 1 d . . . . .
C13 C 0.44065(13) 0.7076(5) 0.5037(3) 0.0472(9) Uani 1 1 d . . . . .
C10 C 0.39784(18) 0.4768(5) 0.3596(3) 0.0562(12) Uani 1 1 d . . . . .
C12 C 0.43018(17) 0.5680(5) 0.5326(3) 0.0595(12) Uani 1 1 d . . . . .
H12 H 0.419104 0.545578 0.607324 0.071 Uiso 1 1 calc R U . . .
C15 C 0.43694(16) 0.6886(5) 0.2960(4) 0.0594(12) Uani 1 1 d . . . . .
H15 H 0.450322 0.722934 0.226459 0.071 Uiso 1 1 calc R U . . .
C14 C 0.45370(17) 0.7544(5) 0.3918(3) 0.0586(12) Uani 1 1 d . . . . .
H14 H 0.474997 0.834945 0.383995 0.070 Uiso 1 1 calc R U . . .
C9 C 0.31933(18) 0.4433(5) 0.2838(4) 0.0660(13) Uani 1 1 d . . . . .
H9A H 0.324687 0.396896 0.208121 0.079 Uiso 1 1 calc R U . . .
H9B H 0.319837 0.552712 0.273370 0.079 Uiso 1 1 calc R U . . .
C8 C 0.27197(19) 0.3978(5) 0.3269(4) 0.0667(13) Uani 1 1 d . . . . .
C11 C 0.43608(18) 0.4478(5) 0.4464(4) 0.0611(13) Uani 1 1 d . . . . .
H11A H 0.432268 0.348431 0.481930 0.073 Uiso 1 1 calc R U . . .
H11B H 0.467302 0.453273 0.410089 0.073 Uiso 1 1 calc R U . . .
C3 C 0.26676(18) 0.3154(6) 0.4230(4) 0.0691(14) Uani 1 1 d . . . . .
C2 C 0.3067(2) 0.2606(7) 0.4889(4) 0.0857(17) Uani 1 1 d . . . . .
H2A H 0.299790 0.159556 0.518208 0.103 Uiso 1 1 calc R U . . .
H2B H 0.312129 0.326784 0.555363 0.103 Uiso 1 1 calc R U . . .
C1 C 0.34981(19) 0.2556(6) 0.4166(4) 0.0702(14) Uani 1 1 d . U . . .
H1A H 0.377144 0.230553 0.464814 0.084 Uiso 1 1 calc R U . . .
H1B H 0.346482 0.177150 0.357560 0.084 Uiso 1 1 calc R U . . .
C7 C 0.2366(2) 0.4406(6) 0.2610(5) 0.0783(16) Uani 1 1 d . . . . .
H7 H 0.242083 0.495431 0.192810 0.094 Uiso 1 1 calc R U . . .
C4 C 0.2211(3) 0.2785(7) 0.4583(5) 0.0921(18) Uani 1 1 d . . . . .
H4 H 0.216283 0.223080 0.526512 0.111 Uiso 1 1 calc R U . . .
C6 C 0.1908(2) 0.4030(7) 0.2942(6) 0.0845(17) Uani 1 1 d . . . . .
H6 H 0.165089 0.432933 0.248118 0.101 Uiso 1 1 calc R U . . .
C5 C 0.1830(2) 0.3237(7) 0.3925(6) 0.093(2) Uani 1 1 d . . . . .
H5 H 0.152034 0.299864 0.415490 0.112 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 F1 1.575(3) . ?
S1 F4 1.593(3) . ?
S1 F2 1.620(3) . ?
S1 F3 1.577(3) . ?
S1 F5 1.585(3) . ?
S1 C13 1.807(4) . ?
N1 C10 1.344(6) . ?
N1 C9 1.464(6) . ?
N1 C1 1.472(6) . ?
N2 C10 1.298(5) . ?
N2 C15 1.357(5) . ?
C13 C12 1.333(6) . ?
C13 C14 1.424(5) . ?
C10 C11 1.515(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.487(6) . ?
C15 H15 0.9500 . ?
C15 C14 1.353(6) . ?
C14 H14 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.502(7) . ?
C8 C3 1.353(7) . ?
C8 C7 1.329(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 C2 1.464(8) . ?
C3 C4 1.410(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.496(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C7 H7 0.9500 . ?
C7 C6 1.408(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(9) . ?
C6 H6 0.9500 . ?
C6 C5 1.369(9) . ?
C5 H5 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
F1 S1 F4 89.79(16) . . ?
F1 S1 F2 90.30(17) . . ?
F1 S1 F3 173.55(15) . . ?
F1 S1 F5 86.91(15) . . ?
F1 S1 C13 93.42(17) . . ?
F4 S1 F2 175.22(15) . . ?
F4 S1 C13 91.61(16) . . ?
F2 S1 C13 93.16(16) . . ?
F3 S1 F4 90.14(17) . . ?
F3 S1 F2 89.24(18) . . ?
F3 S1 F5 86.64(16) . . ?
F3 S1 C13 93.03(17) . . ?
F5 S1 F4 87.68(16) . . ?
F5 S1 F2 87.55(17) . . ?
F5 S1 C13 179.2(2) . . ?
C10 N1 C9 120.0(4) . . ?
C10 N1 C1 125.6(4) . . ?
C9 N1 C1 113.2(4) . . ?
C10 N2 C15 122.5(4) . . ?
C12 C13 S1 118.1(3) . . ?
C12 C13 C14 124.7(4) . . ?
C14 C13 S1 117.2(3) . . ?
N1 C10 C11 121.8(4) . . ?
N2 C10 N1 119.4(4) . . ?
N2 C10 C11 118.8(4) . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 119.0(4) . . ?
C11 C12 H12 120.5 . . ?
N2 C15 H15 115.0 . . ?
C14 C15 N2 129.9(4) . . ?
C14 C15 H15 115.0 . . ?
C13 C14 H14 118.7 . . ?
C15 C14 C13 122.6(4) . . ?
C15 C14 H14 118.7 . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
N1 C9 C8 113.2(4) . . ?
H9A C9 H9B 107.8 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C3 C8 C9 121.8(5) . . ?
C7 C8 C9 114.5(5) . . ?
C7 C8 C3 123.7(5) . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C12 C11 C10 104.3(4) . . ?
C12 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C8 C3 C2 122.3(5) . . ?
C8 C3 C4 118.2(5) . . ?
C4 C3 C2 119.4(5) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 C1 110.9(4) . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
N1 C1 C2 110.1(4) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C8 C7 H7 120.6 . . ?
C8 C7 C6 118.7(6) . . ?
C6 C7 H7 120.6 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(6) . . ?
C5 C4 H4 120.2 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.5(6) . . ?
C5 C6 H6 119.8 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.1(6) . . ?
C6 C5 H5 120.4 . . ?

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 C13 C12 C11 -175.1(3) . . . . ?
S1 C13 C14 C15 -147.4(4) . . . . ?
F1 S1 C13 C12 32.4(4) . . . . ?
F1 S1 C13 C14 -148.2(3) . . . . ?
F4 S1 C13 C12 122.2(4) . . . . ?
F4 S1 C13 C14 -58.3(3) . . . . ?
F2 S1 C13 C12 -58.1(4) . . . . ?
F2 S1 C13 C14 121.3(3) . . . . ?
F3 S1 C13 C12 -147.5(4) . . . . ?
F3 S1 C13 C14 31.9(4) . . . . ?
N1 C10 C11 C12 -99.3(5) . . . . ?
N1 C9 C8 C3 -4.9(6) . . . . ?
N1 C9 C8 C7 177.3(4) . . . . ?
N2 C10 C11 C12 78.7(5) . . . . ?
N2 C15 C14 C13 5.7(9) . . . . ?
C13 C12 C11 C10 -70.0(5) . . . . ?
C10 N1 C9 C8 -155.1(4) . . . . ?
C10 N1 C1 C2 131.0(5) . . . . ?
C10 N2 C15 C14 -32.8(8) . . . . ?
C12 C13 C14 C15 32.1(8) . . . . ?
C15 N2 C10 N1 161.2(4) . . . . ?
C15 N2 C10 C11 -16.9(6) . . . . ?
C14 C13 C12 C11 5.5(7) . . . . ?
C9 N1 C10 N2 -4.8(6) . . . . ?
C9 N1 C10 C11 173.2(4) . . . . ?
C9 N1 C1 C2 -61.7(5) . . . . ?
C9 C8 C3 C2 -2.3(8) . . . . ?
C9 C8 C3 C4 179.4(5) . . . . ?
C9 C8 C7 C6 180.0(4) . . . . ?
C8 C3 C2 C1 -21.6(7) . . . . ?
C8 C3 C4 C5 1.7(8) . . . . ?
C8 C7 C6 C5 -0.1(8) . . . . ?
C3 C8 C7 C6 2.2(8) . . . . ?
C3 C2 C1 N1 52.2(6) . . . . ?
C3 C4 C5 C6 0.2(9) . . . . ?
C2 C3 C4 C5 -176.6(5) . . . . ?
C1 N1 C10 N2 161.7(4) . . . . ?
C1 N1 C10 C11 -20.3(7) . . . . ?
C1 N1 C9 C8 36.8(5) . . . . ?
C7 C8 C3 C2 175.3(5) . . . . ?
C7 C8 C3 C4 -3.0(8) . . . . ?
C7 C6 C5 C4 -1.1(9) . . . . ?
C4 C3 C2 C1 156.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
