# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_exp_1011
_database_code_depnum_ccdc_archive 'CCDC 2283240'
loop_
_audit_author_name
_audit_author_address
'Wenhao Yu'
;Sichuan Normal University
China
;
_audit_update_record             
;
2023-07-20 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H13 F3'
_chemical_formula_sum            'C24 H13 F3'
_chemical_formula_weight         358.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 F1'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.2645(2)
_cell_length_b                   5.52840(10)
_cell_length_c                   22.7571(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.6510(10)
_cell_angle_gamma                90
_cell_volume                     1628.30(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7155
_cell_measurement_temperature    298.1(4)
_cell_measurement_theta_max      76.0010
_cell_measurement_theta_min      3.5310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15594
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.276
_diffrn_reflns_theta_min         3.556
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.1(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  29.00   0.50    0.31    --  -46.37  19.00 -53.00  106
  2  ω   -122.00 -31.00   0.50    0.31    --  -46.37 -19.00 138.00  182
  3  ω     31.00 122.00   0.50    0.31    --   46.37  19.00 -53.00  182
  4  ω   -175.00 -86.00   0.50    1.25    -- -102.00 -19.00 138.00  178
  5  ω     91.00 178.00   0.50    1.25    --  106.06  19.00 -53.00  174
  6  ω    -24.00  29.00   0.50    0.31    --  -46.37  19.00 120.00  106
  7  ω    -29.00  28.00   0.50    0.31    --   46.37 -19.00 138.00  114
  8  ω    -29.00  28.00   0.50    0.31    --   46.37 -19.00   0.00  114
  9  ω    -27.00  44.00   0.50    0.31    --   46.37 -37.00  60.00  142
 10  ω    -69.00 -29.00   0.50    1.25    -- -102.00  61.00  60.00   80
 11  ω    -69.00 -29.00   0.50    1.25    -- -102.00  61.00  30.00   80
 12  ω    -69.00 -29.00   0.50    1.25    -- -102.00  61.00   0.00   80
 13  ω    -69.00 -29.00   0.50    1.25    -- -102.00  61.00 -90.00   80
 14  ω    -69.00 -29.00   0.50    1.25    -- -102.00  61.00 120.00   80
 15  ω     33.00 109.00   0.50    1.25    --  106.06 -94.00  60.00  152
 16  ω     33.00  73.00   0.50    1.25    --  106.06 -61.00-120.00   80
 17  ω     33.00 109.00   0.50    1.25    --  106.06 -94.00  90.00  152
 18  ω     33.00 108.00   0.50    1.25    --  106.06 -77.00   0.00  150
 19  ω     33.00  73.00   0.50    1.25    --  106.06 -61.00 -90.00   80
 20  ω     91.00 178.00   0.50    1.25    --  106.06  30.00  90.00  174
 21  ω     91.00 178.00   0.50    1.25    --  106.06  30.00-150.00  174
 22  ω     91.00 178.00   0.50    1.25    --  106.06  30.00  30.00  174
 23  ω     33.00  73.00   0.50    1.25    --  106.06 -61.00 150.00   80
 24  ω     30.00  56.00   0.50    0.31    --   46.37  57.00 -30.00   52
 25  ω     23.00  59.50   0.50    0.31    --   46.37  77.00  30.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0401915000
_diffrn_orient_matrix_UB_12      0.0509555000
_diffrn_orient_matrix_UB_13      0.0573740000
_diffrn_orient_matrix_UB_21      0.1114483000
_diffrn_orient_matrix_UB_22      0.0466038000
_diffrn_orient_matrix_UB_23      0.0351805000
_diffrn_orient_matrix_UB_31      -0.0116495000
_diffrn_orient_matrix_UB_32      0.2699207000
_diffrn_orient_matrix_UB_33      -0.0168929000
_diffrn_oxdiff_digest_frames     
;
01947a43f330d0574abe738b88c8fcd76400042d3f3
;
_diffrn_oxdiff_digest_hkl        
;
0129f0a94e64fa9e6dda5b21113cae1e277ba1
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2699
_reflns_number_total             3314
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.035
_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)+(0.0665P)²+0.2556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1265
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C5(H5), C1(H1), C3(H3), C15(H15), C6(H6), C21(H21), C16(H16),
 C2(H2), C17(H17), C22(H22), C24(H24), C23(H23)
;
_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
F2 F 0.31937(7) 0.14471(17) 0.61525(4) 0.0662(3) Uani 1 1 d . . . . .
F3 F 0.40830(8) 0.14348(18) 0.52551(5) 0.0696(3) Uani 1 1 d . . . . .
F1 F 0.11891(8) 0.81091(18) 0.54026(4) 0.0736(3) Uani 1 1 d . . . . .
C10 C 0.31441(9) 0.4907(2) 0.47869(6) 0.0403(3) Uani 1 1 d . . . . .
C4 C 0.16915(10) 0.4846(2) 0.63261(6) 0.0429(3) Uani 1 1 d . . . . .
C13 C 0.20604(10) 0.8470(2) 0.43478(6) 0.0414(3) Uani 1 1 d . . . . .
C11 C 0.23676(10) 0.6654(2) 0.48247(6) 0.0402(3) Uani 1 1 d . . . . .
C20 C 0.36536(10) 0.4955(2) 0.42724(6) 0.0430(3) Uani 1 1 d . . . . .
C7 C 0.21699(10) 0.4838(2) 0.57905(6) 0.0432(3) Uani 1 1 d . . . . .
C8 C 0.29067(11) 0.3154(2) 0.57258(6) 0.0460(3) Uani 1 1 d . . . . .
C18 C 0.25434(11) 0.8462(2) 0.38510(6) 0.0454(3) Uani 1 1 d . . . . .
C9 C 0.33747(10) 0.3190(2) 0.52470(7) 0.0459(3) Uani 1 1 d . . . . .
C12 C 0.19289(11) 0.6511(2) 0.53345(6) 0.0452(3) Uani 1 1 d . . . . .
C19 C 0.33504(11) 0.6691(3) 0.38187(6) 0.0484(3) Uani 1 1 d . . . . .
C14 C 0.13012(11) 1.0251(3) 0.43529(6) 0.0496(3) Uani 1 1 d . . . . .
H14 H 0.0971 1.0288 0.4674 0.059 Uiso 1 1 calc R . . . .
C5 C 0.19139(12) 0.6686(3) 0.67470(7) 0.0515(3) Uani 1 1 d . . . . .
H5 H 0.2352 0.7937 0.6691 0.062 Uiso 1 1 calc R . . . .
C1 C 0.08228(12) 0.4852(3) 0.73297(7) 0.0552(4) Uani 1 1 d . . . . .
H1 H 0.0531 0.4851 0.7666 0.066 Uiso 1 1 calc R . . . .
C3 C 0.10278(12) 0.3011(3) 0.64126(7) 0.0527(4) Uani 1 1 d . . . . .
H3 H 0.0876 0.1759 0.6134 0.063 Uiso 1 1 calc R . . . .
C15 C 0.10321(12) 1.1927(3) 0.39026(7) 0.0545(4) Uani 1 1 d . . . . .
H15 H 0.0528 1.3075 0.3921 0.065 Uiso 1 1 calc R . . . .
C6 C 0.14869(13) 0.6674(3) 0.72510(7) 0.0564(4) Uani 1 1 d . . . . .
H6 H 0.1650 0.7899 0.7536 0.068 Uiso 1 1 calc R . . . .
C21 C 0.44361(12) 0.3306(3) 0.42166(7) 0.0553(4) Uani 1 1 d . . . . .
H21 H 0.4648 0.2156 0.4516 0.066 Uiso 1 1 calc R . . . .
C16 C 0.15104(12) 1.1912(3) 0.34210(7) 0.0580(4) Uani 1 1 d . . . . .
H16 H 0.1334 1.3052 0.3115 0.070 Uiso 1 1 calc R . . . .
C2 C 0.05909(13) 0.3034(3) 0.69099(7) 0.0575(4) Uani 1 1 d . . . . .
H2 H 0.0137 0.1811 0.6961 0.069 Uiso 1 1 calc R . . . .
C17 C 0.22432(12) 1.0211(3) 0.33979(7) 0.0578(4) Uani 1 1 d . . . . .
H17 H 0.2557 1.0206 0.3070 0.069 Uiso 1 1 calc R . . . .
C22 C 0.48946(14) 0.3354(3) 0.37307(8) 0.0649(4) Uani 1 1 d . . . . .
H22 H 0.5406 0.2238 0.3703 0.078 Uiso 1 1 calc R . . . .
C24 C 0.38431(16) 0.6687(3) 0.33302(8) 0.0701(5) Uani 1 1 d . . . . .
H24 H 0.3650 0.7834 0.3027 0.084 Uiso 1 1 calc R . . . .
C23 C 0.45957(16) 0.5055(4) 0.32864(9) 0.0755(5) Uani 1 1 d . . . . .
H23 H 0.4905 0.5094 0.2957 0.091 Uiso 1 1 calc R . . . .


_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
F2 C8 1.3476(15) . ?
F3 C9 1.3479(15) . ?
F1 C12 1.3544(15) . ?
C10 C11 1.4280(18) . ?
C10 C20 1.4746(18) . ?
C10 C9 1.3968(19) . ?
C4 C7 1.4925(18) . ?
C4 C5 1.384(2) . ?
C4 C3 1.385(2) . ?
C13 C11 1.4692(19) . ?
C13 C18 1.4163(19) . ?
C13 C14 1.4101(19) . ?
C11 C12 1.4096(19) . ?
C20 C19 1.403(2) . ?
C20 C21 1.4077(19) . ?
C7 C8 1.3812(19) . ?
C7 C12 1.3742(19) . ?
C8 C9 1.367(2) . ?
C18 C19 1.464(2) . ?
C18 C17 1.406(2) . ?
C19 C24 1.408(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(2) . ?
C1 H1 0.9300 . ?
C1 C6 1.375(2) . ?
C1 C2 1.375(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.380(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(2) . ?
C6 H6 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.374(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.362(2) . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.374(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.366(3) . ?
C23 H23 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
C11 C10 C20 119.85(12) . . ?
C9 C10 C11 117.18(12) . . ?
C9 C10 C20 122.96(12) . . ?
C5 C4 C7 120.20(12) . . ?
C5 C4 C3 119.06(13) . . ?
C3 C4 C7 120.74(12) . . ?
C18 C13 C11 119.12(12) . . ?
C14 C13 C11 123.65(12) . . ?
C14 C13 C18 117.23(12) . . ?
C10 C11 C13 120.31(12) . . ?
C12 C11 C10 116.42(12) . . ?
C12 C11 C13 123.27(12) . . ?
C19 C20 C10 119.29(12) . . ?
C19 C20 C21 118.35(13) . . ?
C21 C20 C10 122.36(13) . . ?
C8 C7 C4 121.75(12) . . ?
C12 C7 C4 123.00(12) . . ?
C12 C7 C8 115.23(12) . . ?
F2 C8 C7 119.35(12) . . ?
F2 C8 C9 118.60(12) . . ?
C9 C8 C7 122.03(12) . . ?
C13 C18 C19 120.37(12) . . ?
C17 C18 C13 118.57(13) . . ?
C17 C18 C19 121.05(13) . . ?
F3 C9 C10 122.49(12) . . ?
F3 C9 C8 114.53(12) . . ?
C8 C9 C10 122.98(12) . . ?
F1 C12 C11 119.85(12) . . ?
F1 C12 C7 114.02(12) . . ?
C7 C12 C11 126.13(12) . . ?
C20 C19 C18 121.04(12) . . ?
C20 C19 C24 118.19(14) . . ?
C24 C19 C18 120.77(14) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 C13 122.39(14) . . ?
C15 C14 H14 118.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.37(14) . . ?
C6 C5 H5 119.8 . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.82(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.27(14) . . ?
C2 C3 H3 119.9 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.97(14) . . ?
C16 C15 H15 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.03(14) . . ?
C1 C6 H6 120.0 . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.68(15) . . ?
C22 C21 H21 119.2 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.39(14) . . ?
C17 C16 H16 120.3 . . ?
C1 C2 C3 120.42(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C18 C17 H17 118.8 . . ?
C16 C17 C18 122.45(14) . . ?
C16 C17 H17 118.8 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.88(15) . . ?
C23 C22 H22 120.1 . . ?
C19 C24 H24 118.9 . . ?
C23 C24 C19 122.14(16) . . ?
C23 C24 H24 118.9 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.75(16) . . ?
C24 C23 H23 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 9.307
_oxdiff_exptl_absorpt_empirical_full_min 0.334
