# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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. 
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data_xiongt230705_1_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 2378635'
loop_
_audit_author_name
_audit_author_address
SDZ
;NENU
China
;
_audit_update_record             
;
2024-08-20 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_audit_creation_date             2023-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H12 F5 N O'
_chemical_formula_sum            'C21 H12 F5 N O'
_chemical_formula_weight         389.32
_chemical_absolute_configuration rmad
_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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7489(9)
_cell_length_b                   15.981(3)
_cell_length_c                   19.362(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1778.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9612
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      63.735
_cell_measurement_theta_min      2.282
_shelx_estimated_absorpt_T_max   0.811
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0783 after correction.
The Ratio of minimum to maximum transmission is 0.7814.
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    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15788
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        63.815
_diffrn_reflns_theta_max         63.815
_diffrn_reflns_theta_min         3.586
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2628
_reflns_number_total             2922
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.04(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.083
_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)+(0.0343P)²+0.3202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0815
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.04(19)
 -0.04(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C02G(H02G)
3.b Aromatic/amide H refined with riding coordinates:
 C01O(H01O), C01Q(H01Q), C01T(H01T), C023(H023), C029(H029), C02C(H02C),
 C02I(H02I), C030(H030)
3.c Idealised Me refined as rotating group:
 C02W(H02A,H02B,H02D)
;
_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
F001 F 0.2111(3) 0.96693(11) 0.87160(8) 0.0668(6) Uani 1 1 d . . . . .
F005 F 0.1113(3) 0.96635(11) 1.00527(9) 0.0706(6) Uani 1 1 d . . . . .
F00B F 0.8980(3) 0.81482(11) 0.91778(9) 0.0692(6) Uani 1 1 d . . . . .
F00E F 0.7969(3) 0.81665(12) 1.05144(9) 0.0799(7) Uani 1 1 d . . . . .
F00N F -0.0722(5) 0.70894(15) 0.67184(11) 0.1084(9) Uani 1 1 d . . . . .
O00L O -0.0510(4) 0.87862(15) 0.65296(10) 0.0742(7) Uani 1 1 d . . . . .
N033 N 0.3426(8) 0.9008(2) 1.16020(16) 0.1025(12) Uani 1 1 d . . . . .
C00V C 0.4327(5) 0.84445(17) 0.77256(12) 0.0503(7) Uani 1 1 d . . . . .
C00W C 0.7014(5) 0.85372(16) 0.93779(14) 0.0493(7) Uani 1 1 d . . . . .
C00Z C 0.5601(4) 0.89176(16) 0.88911(13) 0.0454(7) Uani 1 1 d . . . . .
C017 C -0.0282(5) 0.87092(17) 0.58220(14) 0.0511(7) Uani 1 1 d . . . . .
C01B C 0.3609(5) 0.92894(16) 0.91486(13) 0.0481(7) Uani 1 1 d . . . . .
C01L C 0.3078(5) 0.92964(16) 0.98377(14) 0.0496(7) Uani 1 1 d . . . . .
C01O C -0.2098(5) 0.90191(18) 0.54363(16) 0.0599(8) Uani 1 1 d . . . . .
H01O H -0.337087 0.926321 0.565362 0.072 Uiso 1 1 calc R U . . .
C01Q C -0.2021(6) 0.89663(19) 0.47278(16) 0.0642(8) Uani 1 1 d . . . . .
H01Q H -0.325189 0.917047 0.446570 0.077 Uiso 1 1 calc R U . . .
C01T C 0.2780(5) 0.88321(18) 0.72827(13) 0.0527(7) Uani 1 1 d . . . . .
H01T H 0.288064 0.940664 0.721236 0.063 Uiso 1 1 calc R U . . .
C01Z C 0.4518(5) 0.89203(17) 1.03174(14) 0.0522(7) Uani 1 1 d . . . . .
C023 C 0.1624(5) 0.83592(18) 0.55089(14) 0.0545(8) Uani 1 1 d . . . . .
H023 H 0.285454 0.815731 0.577233 0.065 Uiso 1 1 calc R U . . .
C026 C 0.6510(5) 0.85400(17) 1.00716(14) 0.0526(7) Uani 1 1 d . . . . .
C027 C 0.1090(6) 0.8378(2) 0.69435(13) 0.0600(8) Uani 1 1 d . . . . .
C029 C 0.4138(7) 0.75838(18) 0.78142(15) 0.0687(9) Uani 1 1 d . . . . .
H029 H 0.517650 0.731007 0.810500 0.082 Uiso 1 1 calc R U . . .
C02C C 0.1691(6) 0.83108(18) 0.47959(14) 0.0597(8) Uani 1 1 d . . . . .
H02C H 0.297462 0.807276 0.457945 0.072 Uiso 1 1 calc R U . . .
C02G C 0.6188(5) 0.89152(18) 0.81272(13) 0.0528(7) Uani 1 1 d . . . . .
H02G H 0.763523 0.859685 0.807616 0.063 Uiso 1 1 calc R U . . .
C02I C -0.0120(6) 0.86108(18) 0.44038(16) 0.0638(9) Uani 1 1 d . . . . .
H02I H -0.006627 0.857493 0.392461 0.077 Uiso 1 1 calc R U . . .
C02U C 0.3957(7) 0.8955(2) 1.10346(16) 0.0693(9) Uani 1 1 d . . . . .
C02W C 0.6694(6) 0.98082(19) 0.78717(16) 0.0645(9) Uani 1 1 d . . . . .
H02A H 0.531927 1.014438 0.791840 0.097 Uiso 1 1 calc R U . . .
H02B H 0.715244 0.979020 0.739511 0.097 Uiso 1 1 calc R U . . .
H02D H 0.792624 1.004724 0.814195 0.097 Uiso 1 1 calc R U . . .
C02X C 0.0944(7) 0.7528(2) 0.70539(15) 0.0708(10) Uani 1 1 d . . . . .
C030 C 0.2439(8) 0.7127(2) 0.74791(16) 0.0798(12) Uani 1 1 d . . . . .
H030 H 0.232554 0.655215 0.754511 0.096 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
F001 C01B 1.346(3) . ?
F005 C01L 1.339(3) . ?
F00B C00W 1.347(3) . ?
F00E C026 1.340(3) . ?
F00N C02X 1.353(4) . ?
O00L C017 1.382(3) . ?
O00L C027 1.383(4) . ?
N033 C02U 1.143(4) . ?
C00V C01T 1.382(4) . ?
C00V C029 1.390(4) . ?
C00V C02G 1.522(4) . ?
C00W C00Z 1.385(4) . ?
C00W C026 1.374(4) . ?
C00Z C01B 1.383(4) . ?
C00Z C02G 1.517(4) . ?
C017 C01O 1.376(4) . ?
C017 C023 1.372(4) . ?
C01B C01L 1.369(4) . ?
C01L C01Z 1.382(4) . ?
C01O H01O 0.9300 . ?
C01O C01Q 1.375(4) . ?
C01Q H01Q 0.9300 . ?
C01Q C02I 1.382(5) . ?
C01T H01T 0.9300 . ?
C01T C027 1.380(4) . ?
C01Z C026 1.381(4) . ?
C01Z C02U 1.427(4) . ?
C023 H023 0.9300 . ?
C023 C02C 1.383(4) . ?
C027 C02X 1.377(5) . ?
C029 H029 0.9300 . ?
C029 C030 1.381(5) . ?
C02C H02C 0.9300 . ?
C02C C02I 1.375(4) . ?
C02G H02G 0.9800 . ?
C02G C02W 1.538(4) . ?
C02I H02I 0.9300 . ?
C02W H02A 0.9600 . ?
C02W H02B 0.9600 . ?
C02W H02D 0.9600 . ?
C02X C030 1.352(5) . ?
C030 H030 0.9300 . ?

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
C017 O00L C027 118.0(2) . . ?
C01T C00V C029 118.0(3) . . ?
C01T C00V C02G 123.2(2) . . ?
C029 C00V C02G 118.7(3) . . ?
F00B C00W C00Z 119.9(2) . . ?
F00B C00W C026 117.4(2) . . ?
C026 C00W C00Z 122.7(3) . . ?
C00W C00Z C02G 122.1(2) . . ?
C01B C00Z C00W 115.4(2) . . ?
C01B C00Z C02G 122.5(2) . . ?
C01O C017 O00L 115.8(2) . . ?
C023 C017 O00L 123.4(2) . . ?
C023 C017 C01O 120.9(3) . . ?
F001 C01B C00Z 120.0(2) . . ?
F001 C01B C01L 117.4(2) . . ?
C01L C01B C00Z 122.7(2) . . ?
F005 C01L C01B 119.7(2) . . ?
F005 C01L C01Z 119.1(2) . . ?
C01B C01L C01Z 121.2(2) . . ?
C017 C01O H01O 120.2 . . ?
C01Q C01O C017 119.7(3) . . ?
C01Q C01O H01O 120.2 . . ?
C01O C01Q H01Q 119.9 . . ?
C01O C01Q C02I 120.2(3) . . ?
C02I C01Q H01Q 119.9 . . ?
C00V C01T H01T 119.6 . . ?
C027 C01T C00V 120.8(3) . . ?
C027 C01T H01T 119.6 . . ?
C01L C01Z C02U 120.1(3) . . ?
C026 C01Z C01L 117.2(2) . . ?
C026 C01Z C02U 122.7(3) . . ?
C017 C023 H023 120.5 . . ?
C017 C023 C02C 119.1(3) . . ?
C02C C023 H023 120.5 . . ?
F00E C026 C00W 119.5(3) . . ?
F00E C026 C01Z 119.6(2) . . ?
C00W C026 C01Z 120.9(2) . . ?
C01T C027 O00L 119.7(3) . . ?
C02X C027 O00L 121.0(3) . . ?
C02X C027 C01T 119.2(3) . . ?
C00V C029 H029 119.3 . . ?
C030 C029 C00V 121.3(3) . . ?
C030 C029 H029 119.3 . . ?
C023 C02C H02C 119.6 . . ?
C02I C02C C023 120.7(3) . . ?
C02I C02C H02C 119.6 . . ?
C00V C02G H02G 106.8 . . ?
C00V C02G C02W 115.3(2) . . ?
C00Z C02G C00V 110.0(2) . . ?
C00Z C02G H02G 106.8 . . ?
C00Z C02G C02W 110.7(2) . . ?
C02W C02G H02G 106.8 . . ?
C01Q C02I H02I 120.3 . . ?
C02C C02I C01Q 119.4(3) . . ?
C02C C02I H02I 120.3 . . ?
N033 C02U C01Z 176.9(4) . . ?
C02G C02W H02A 109.5 . . ?
C02G C02W H02B 109.5 . . ?
C02G C02W H02D 109.5 . . ?
H02A C02W H02B 109.5 . . ?
H02A C02W H02D 109.5 . . ?
H02B C02W H02D 109.5 . . ?
F00N C02X C027 118.6(3) . . ?
C030 C02X F00N 119.8(3) . . ?
C030 C02X C027 121.5(3) . . ?
C029 C030 H030 120.5 . . ?
C02X C030 C029 119.0(3) . . ?
C02X C030 H030 120.5 . . ?

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
F001 C01B C01L F005 0.9(4) . . . . ?
F001 C01B C01L C01Z 179.9(2) . . . . ?
F005 C01L C01Z C026 179.2(2) . . . . ?
F005 C01L C01Z C02U -2.6(4) . . . . ?
F00B C00W C00Z C01B 179.2(2) . . . . ?
F00B C00W C00Z C02G -0.1(4) . . . . ?
F00B C00W C026 F00E 0.3(4) . . . . ?
F00B C00W C026 C01Z -179.5(2) . . . . ?
F00N C02X C030 C029 179.6(3) . . . . ?
O00L C017 C01O C01Q -179.8(3) . . . . ?
O00L C017 C023 C02C -179.9(3) . . . . ?
O00L C027 C02X F00N 3.6(4) . . . . ?
O00L C027 C02X C030 -177.3(3) . . . . ?
C00V C01T C027 O00L 176.8(2) . . . . ?
C00V C01T C027 C02X 0.4(4) . . . . ?
C00V C029 C030 C02X 0.4(5) . . . . ?
C00W C00Z C01B F001 -179.4(2) . . . . ?
C00W C00Z C01B C01L 1.1(4) . . . . ?
C00W C00Z C02G C00V 117.0(3) . . . . ?
C00W C00Z C02G C02W -114.4(3) . . . . ?
C00Z C00W C026 F00E -179.3(2) . . . . ?
C00Z C00W C026 C01Z 0.9(4) . . . . ?
C00Z C01B C01L F005 -179.6(2) . . . . ?
C00Z C01B C01L C01Z -0.6(4) . . . . ?
C017 O00L C027 C01T 106.6(3) . . . . ?
C017 O00L C027 C02X -77.0(4) . . . . ?
C017 C01O C01Q C02I -0.6(5) . . . . ?
C017 C023 C02C C02I 0.2(5) . . . . ?
C01B C00Z C02G C00V -62.2(3) . . . . ?
C01B C00Z C02G C02W 66.4(3) . . . . ?
C01B C01L C01Z C026 0.1(4) . . . . ?
C01B C01L C01Z C02U 178.3(3) . . . . ?
C01L C01Z C026 F00E 180.0(2) . . . . ?
C01L C01Z C026 C00W -0.2(4) . . . . ?
C01O C017 C023 C02C -0.8(4) . . . . ?
C01O C01Q C02I C02C 0.0(5) . . . . ?
C01T C00V C029 C030 -0.9(5) . . . . ?
C01T C00V C02G C00Z 110.3(3) . . . . ?
C01T C00V C02G C02W -15.7(4) . . . . ?
C01T C027 C02X F00N 180.0(3) . . . . ?
C01T C027 C02X C030 -1.0(5) . . . . ?
C023 C017 C01O C01Q 1.0(5) . . . . ?
C023 C02C C02I C01Q 0.2(5) . . . . ?
C026 C00W C00Z C01B -1.2(4) . . . . ?
C026 C00W C00Z C02G 179.5(2) . . . . ?
C027 O00L C017 C01O 170.6(3) . . . . ?
C027 O00L C017 C023 -10.2(4) . . . . ?
C027 C02X C030 C029 0.6(5) . . . . ?
C029 C00V C01T C027 0.5(4) . . . . ?
C029 C00V C02G C00Z -68.6(3) . . . . ?
C029 C00V C02G C02W 165.3(3) . . . . ?
C02G C00V C01T C027 -178.5(2) . . . . ?
C02G C00V C029 C030 178.1(3) . . . . ?
C02G C00Z C01B F001 -0.2(4) . . . . ?
C02G C00Z C01B C01L -179.7(3) . . . . ?
C02U C01Z C026 F00E 1.8(4) . . . . ?
C02U C01Z C026 C00W -178.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.04(19)
2 -0.04(19)

