# Supplementary Information (SI) for ChemComm.
# 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. 
# 
#######################################################################

data_12_a
_database_code_depnum_ccdc_archive 'CCDC 2390990'
loop_
_audit_author_name
_audit_author_address
'Xin-Xing Wu' lzu
_audit_update_record             
;
2024-10-15 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 F'
_chemical_formula_weight         312.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.689(2)
_cell_length_b                   17.293(3)
_cell_length_c                   8.4188(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.698(2)
_cell_angle_gamma                90
_cell_volume                     1660.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9446
_cell_measurement_theta_min      2.7455
_cell_measurement_theta_max      27.465

_exptl_crystal_description       block
_exptl_crystal_colour            ?colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33387
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.746
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3816
_reflns_number_gt                2825
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3816
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1549
_refine_ls_goodness_of_fit_ref   1.273
_refine_ls_restrained_S_all      1.273
_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
F1 F 0.24318(10) 0.29005(8) 0.70784(17) 0.0971(4) Uani 1 1 d . . . . .
C17 C 0.74885(13) 0.47788(8) 0.83024(16) 0.0456(3) Uani 1 1 d . . . . .
C8 C 0.67088(13) 0.42832(7) 0.70936(15) 0.0445(3) Uani 1 1 d . . . . .
C12 C 0.79948(13) 0.37342(8) 0.51822(15) 0.0468(4) Uani 1 1 d . . . . .
C7 C 0.69473(13) 0.39604(7) 0.57347(15) 0.0447(3) Uani 1 1 d . . . . .
C5 C 0.51008(13) 0.34962(8) 0.59665(17) 0.0474(4) Uani 1 1 d . . . . .
C4 C 0.55550(13) 0.40004(7) 0.72627(16) 0.0458(4) Uani 1 1 d . . . . .
C6 C 0.59305(14) 0.34742(8) 0.48241(15) 0.0481(4) Uani 1 1 d . . . . .
C11 C 0.77735(14) 0.30028(8) 0.44553(16) 0.0506(4) Uani 1 1 d . . . . .
C13 C 0.90931(15) 0.40732(9) 0.53562(18) 0.0571(4) Uani 1 1 d . . . . .
H13 H 0.9244 0.4557 0.5839 0.068 Uiso 1 1 calc R U . . .
C18 C 0.78180(15) 0.45681(9) 0.99369(17) 0.0559(4) Uani 1 1 d . . . . .
H18 H 0.7543 0.4108 1.0287 0.067 Uiso 1 1 calc R U . . .
C22 C 0.79065(15) 0.54750(9) 0.78301(18) 0.0556(4) Uani 1 1 d . . . . .
H22 H 0.7694 0.5629 0.6747 0.067 Uiso 1 1 calc R U . . .
C3 C 0.49399(15) 0.41311(9) 0.84783(19) 0.0554(4) Uani 1 1 d . . . . .
H3 H 0.5238 0.4467 0.9332 0.067 Uiso 1 1 calc R U . . .
C00E C 0.40290(15) 0.31377(9) 0.5870(2) 0.0605(4) Uani 1 1 d . . . . .
H00E H 0.3705 0.2816 0.5003 0.073 Uiso 1 1 calc R U . . .
C21 C 0.86354(16) 0.59411(10) 0.8952(2) 0.0655(5) Uani 1 1 d . . . . .
H21 H 0.8908 0.6406 0.8621 0.079 Uiso 1 1 calc R U . . .
C19 C 0.85494(15) 0.50375(11) 1.10392(19) 0.0651(5) Uani 1 1 d . . . . .
H19 H 0.8768 0.4889 1.2125 0.078 Uiso 1 1 calc R U . . .
C20 C 0.89561(15) 0.57192(11) 1.0551(2) 0.0654(5) Uani 1 1 d . . . . .
H20 H 0.9450 0.6032 1.1303 0.078 Uiso 1 1 calc R U . . .
C2 C 0.38845(16) 0.37589(10) 0.8409(2) 0.0644(5) Uani 1 1 d . . . . .
H2 H 0.3471 0.3833 0.9223 0.077 Uiso 1 1 calc R U . . .
C10 C 0.65633(14) 0.27216(9) 0.45379(17) 0.0536(4) Uani 1 1 d . . . . .
H10A H 0.6598 0.2361 0.5430 0.064 Uiso 1 1 calc R U . . .
H10B H 0.6177 0.2475 0.3528 0.064 Uiso 1 1 calc R U . . .
C1 C 0.34581(15) 0.32791(10) 0.7122(2) 0.0658(5) Uani 1 1 d . . . . .
C16 C 0.86410(17) 0.26237(10) 0.38851(19) 0.0643(5) Uani 1 1 d . . . . .
H16 H 0.8494 0.2142 0.3390 0.077 Uiso 1 1 calc R U . . .
C15 C 0.97319(18) 0.29644(11) 0.4055(2) 0.0719(5) Uani 1 1 d . . . . .
H15 H 1.0317 0.2712 0.3666 0.086 Uiso 1 1 calc R U . . .
C14 C 0.99598(17) 0.36791(11) 0.4800(2) 0.0683(5) Uani 1 1 d . . . . .
H14 H 1.0702 0.3897 0.4928 0.082 Uiso 1 1 calc R U . . .
C9 C 0.53507(16) 0.38429(11) 0.31776(18) 0.0696(5) Uani 1 1 d . . . . .
H9A H 0.4696 0.3533 0.2650 0.104 Uiso 1 1 calc R U . . .
H9B H 0.5911 0.3872 0.2500 0.104 Uiso 1 1 calc R U . . .
H9C H 0.5084 0.4354 0.3357 0.104 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
F1 C1 1.360(2) . ?
C17 C22 1.390(2) . ?
C17 C18 1.393(2) . ?
C17 C8 1.4809(19) . ?
C8 C7 1.3558(17) . ?
C8 C4 1.471(2) . ?
C12 C13 1.389(2) . ?
C12 C11 1.404(2) . ?
C12 C7 1.456(2) . ?
C7 C6 1.519(2) . ?
C5 C00E 1.384(2) . ?
C5 C4 1.4066(19) . ?
C5 C6 1.509(2) . ?
C4 C3 1.392(2) . ?
C6 C9 1.5409(19) . ?
C6 C10 1.542(2) . ?
C11 C16 1.379(2) . ?
C11 C10 1.512(2) . ?
C13 C14 1.385(2) . ?
C13 H13 0.9300 . ?
C18 C19 1.379(2) . ?
C18 H18 0.9300 . ?
C22 C21 1.384(2) . ?
C22 H22 0.9300 . ?
C3 C2 1.381(2) . ?
C3 H3 0.9300 . ?
C00E C1 1.388(2) . ?
C00E H00E 0.9300 . ?
C21 C20 1.371(2) . ?
C21 H21 0.9300 . ?
C19 C20 1.368(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C2 C1 1.369(3) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C16 C15 1.383(3) . ?
C16 H16 0.9300 . ?
C15 C14 1.385(2) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C22 C17 C18 118.09(13) . . ?
C22 C17 C8 120.44(13) . . ?
C18 C17 C8 121.47(13) . . ?
C7 C8 C4 107.93(12) . . ?
C7 C8 C17 127.48(14) . . ?
C4 C8 C17 124.39(12) . . ?
C13 C12 C11 120.23(14) . . ?
C13 C12 C7 132.49(14) . . ?
C11 C12 C7 107.10(13) . . ?
C8 C7 C12 136.35(13) . . ?
C8 C7 C6 111.75(13) . . ?
C12 C7 C6 108.05(11) . . ?
C00E C5 C4 120.37(14) . . ?
C00E C5 C6 130.66(14) . . ?
C4 C5 C6 108.92(13) . . ?
C3 C4 C5 120.20(15) . . ?
C3 C4 C8 130.53(14) . . ?
C5 C4 C8 109.19(12) . . ?
C5 C6 C7 101.87(11) . . ?
C5 C6 C9 110.23(13) . . ?
C7 C6 C9 111.44(12) . . ?
C5 C6 C10 121.23(12) . . ?
C7 C6 C10 101.37(12) . . ?
C9 C6 C10 109.87(12) . . ?
C16 C11 C12 120.05(15) . . ?
C16 C11 C10 129.05(14) . . ?
C12 C11 C10 110.75(12) . . ?
C14 C13 C12 118.96(16) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C19 C18 C17 120.43(15) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C21 C22 C17 120.78(15) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C2 C3 C4 119.60(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C00E C1 117.18(16) . . ?
C5 C00E H00E 121.4 . . ?
C1 C00E H00E 121.4 . . ?
C20 C21 C22 120.13(16) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C20 C19 C18 120.68(15) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.89(15) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C1 C2 C3 118.84(16) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C11 C10 C6 102.80(12) . . ?
C11 C10 H10A 111.2 . . ?
C6 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C6 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
F1 C1 C2 118.61(16) . . ?
F1 C1 C00E 117.60(17) . . ?
C2 C1 C00E 123.77(16) . . ?
C11 C16 C15 119.55(16) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C15 C14 120.53(16) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C13 C14 C15 120.66(18) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039



