# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_lj-797
_database_code_depnum_ccdc_archive 'CCDC 2222843'
loop_
_audit_author_name
_audit_author_address
'Jie Lin'
;Dalian Institute of Chemical Physics, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2023-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H13 F5'
_chemical_formula_weight         360.31

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.338(3)
_cell_length_b                   5.6821(11)
_cell_length_c                   12.867(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.49(3)
_cell_angle_gamma                90
_cell_volume                     827.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1278
_cell_measurement_theta_min      5.769
_cell_measurement_theta_max      29.578

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5487
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4070
_diffrn_reflns_number            2276
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.601
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.894
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.598
_diffrn_reflns_point_group_measured_fraction_full 0.581
_reflns_number_total             1741
_reflns_number_gt                1552
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.172
_reflns_Friedel_fraction_max     0.197
_reflns_Friedel_fraction_full    0.191

_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       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0492P)²+0.0518P] 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     SHELXL
_refine_ls_extinction_coef       0.086(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 237 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.3(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1741
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_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 0.15071(15) 0.7940(3) 0.76003(13) 0.0581(5) Uani 1 1 d . . . . .
F2 F -0.03293(14) 0.6592(4) 0.80585(15) 0.0741(6) Uani 1 1 d . . . . .
F3 F -0.02341(15) 0.2543(4) 0.92075(17) 0.0790(6) Uani 1 1 d . . . . .
F4 F 0.17558(18) -0.0115(4) 0.99175(15) 0.0714(6) Uani 1 1 d . . . . .
F5 F 0.35795(14) 0.1171(4) 0.94398(12) 0.0603(5) Uani 1 1 d . . . . .
C1 C 0.1586(2) 0.5898(6) 0.81486(19) 0.0413(7) Uani 1 1 d . . . . .
C2 C 0.0638(2) 0.5233(6) 0.8394(2) 0.0481(8) Uani 1 1 d . . . . .
C3 C 0.0691(2) 0.3206(6) 0.8985(2) 0.0491(8) Uani 1 1 d . . . . .
C4 C 0.1688(3) 0.1869(6) 0.9335(2) 0.0467(7) Uani 1 1 d . . . . .
C5 C 0.2623(2) 0.2556(6) 0.9084(2) 0.0401(7) Uani 1 1 d . . . . .
C6 C 0.2609(2) 0.4576(5) 0.84809(18) 0.0375(6) Uani 1 1 d . . . . .
C7 C 0.3674(2) 0.5339(5) 0.8312(2) 0.0426(7) Uani 1 1 d . . . . .
H7 H 0.4381 0.5289 0.8950 0.051 Uiso 1 1 calc R U . . .
C8 C 0.3747(2) 0.6089(5) 0.73582(19) 0.0388(6) Uani 1 1 d . . . . .
C9 C 0.2763(2) 0.6020(5) 0.62309(19) 0.0383(6) Uani 1 1 d . . . . .
C10 C 0.2607(2) 0.7853(6) 0.5471(2) 0.0463(7) Uani 1 1 d . . . . .
H10 H 0.3122 0.9129 0.5675 0.056 Uiso 1 1 calc R U . . .
C11 C 0.1688(3) 0.7790(6) 0.4410(2) 0.0566(8) Uani 1 1 d . . . . .
H11 H 0.1592 0.9033 0.3910 0.068 Uiso 1 1 calc R U . . .
C12 C 0.0925(3) 0.5948(7) 0.4084(2) 0.0595(9) Uani 1 1 d . . . . .
H12 H 0.0311 0.5931 0.3370 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1070(3) 0.4105(6) 0.4822(2) 0.0553(8) Uani 1 1 d . . . . .
H13 H 0.0551 0.2837 0.4607 0.066 Uiso 1 1 calc R U . . .
C14 C 0.1984(3) 0.4139(6) 0.5881(2) 0.0495(7) Uani 1 1 d . . . . .
H14 H 0.2079 0.2876 0.6369 0.059 Uiso 1 1 calc R U . . .
C15 C 0.4895(2) 0.7125(6) 0.7444(2) 0.0407(7) Uani 1 1 d . . . . .
C16 C 0.5347(2) 0.9033(7) 0.8158(2) 0.0527(8) Uani 1 1 d . . . . .
H16 H 0.4925 0.9625 0.8559 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6407(3) 1.0086(7) 0.8293(2) 0.0661(10) Uani 1 1 d . . . . .
H17 H 0.6697 1.1356 0.8781 0.079 Uiso 1 1 calc R U . . .
C18 C 0.7022(3) 0.9214(9) 0.7689(3) 0.0718(11) Uani 1 1 d . . . . .
H18 H 0.7734 0.9898 0.7766 0.086 Uiso 1 1 calc R U . . .
C19 C 0.6584(3) 0.7350(8) 0.6981(3) 0.0666(10) Uani 1 1 d . . . . .
H19 H 0.7018 0.6778 0.6587 0.080 Uiso 1 1 calc R U . . .
C20 C 0.5525(2) 0.6265(6) 0.6819(2) 0.0495(7) Uani 1 1 d . . . . .
C21 C 0.5100(3) 0.4224(8) 0.6036(3) 0.0670(10) Uani 1 1 d . . . . .
H21A H 0.4839 0.3000 0.6397 0.101 Uiso 1 1 calc R U . . .
H21B H 0.5732 0.3645 0.5851 0.101 Uiso 1 1 calc R U . . .
H21C H 0.4454 0.4711 0.5356 0.101 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 1.341(3) . ?
F2 C2 1.340(3) . ?
F3 C3 1.337(3) . ?
F4 C4 1.338(4) . ?
F5 C5 1.338(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.382(4) . ?
C2 C3 1.367(5) . ?
C3 C4 1.360(4) . ?
C4 C5 1.373(4) . ?
C5 C6 1.382(4) . ?
C6 C7 1.480(3) . ?
C7 C8 1.335(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.475(3) . ?
C8 C15 1.498(3) . ?
C9 C14 1.387(4) . ?
C9 C10 1.389(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.386(4) . ?
C15 C20 1.410(4) . ?
C16 C17 1.384(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.361(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.487(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
F1 C1 C2 117.9(3) . . ?
F1 C1 C6 119.9(2) . . ?
C2 C1 C6 122.2(3) . . ?
F2 C2 C3 120.2(3) . . ?
F2 C2 C1 119.7(3) . . ?
C3 C2 C1 120.1(3) . . ?
F3 C3 C4 120.5(3) . . ?
F3 C3 C2 120.1(3) . . ?
C4 C3 C2 119.4(2) . . ?
F4 C4 C3 120.2(3) . . ?
F4 C4 C5 120.1(3) . . ?
C3 C4 C5 119.8(3) . . ?
F5 C5 C4 117.5(3) . . ?
F5 C5 C6 119.5(2) . . ?
C4 C5 C6 123.0(3) . . ?
C5 C6 C1 115.5(2) . . ?
C5 C6 C7 120.8(2) . . ?
C1 C6 C7 123.4(3) . . ?
C8 C7 C6 128.1(2) . . ?
C8 C7 H7 115.9 . . ?
C6 C7 H7 115.9 . . ?
C7 C8 C9 124.4(2) . . ?
C7 C8 C15 117.8(2) . . ?
C9 C8 C15 117.8(2) . . ?
C14 C9 C10 117.8(2) . . ?
C14 C9 C8 122.1(2) . . ?
C10 C9 C8 120.1(2) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 121.3(3) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C16 C15 C20 118.8(3) . . ?
C16 C15 C8 118.4(2) . . ?
C20 C15 C8 122.8(3) . . ?
C17 C16 C15 122.1(3) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C18 C17 C16 118.7(3) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 123.1(3) . . ?
C18 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C19 C20 C15 117.5(3) . . ?
C19 C20 C21 120.4(3) . . ?
C15 C20 C21 122.0(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
F1 C1 C2 F2 1.6(4) . . . . ?
C6 C1 C2 F2 179.5(2) . . . . ?
F1 C1 C2 C3 -177.8(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
F2 C2 C3 F3 1.6(4) . . . . ?
C1 C2 C3 F3 -179.0(3) . . . . ?
F2 C2 C3 C4 -178.9(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
F3 C3 C4 F4 -0.7(4) . . . . ?
C2 C3 C4 F4 179.8(2) . . . . ?
F3 C3 C4 C5 179.0(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
F4 C4 C5 F5 0.2(4) . . . . ?
C3 C4 C5 F5 -179.5(2) . . . . ?
F4 C4 C5 C6 179.6(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
F5 C5 C6 C1 -180.0(2) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
F5 C5 C6 C7 -5.5(3) . . . . ?
C4 C5 C6 C7 175.0(3) . . . . ?
F1 C1 C6 C5 177.2(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
F1 C1 C6 C7 2.9(4) . . . . ?
C2 C1 C6 C7 -174.9(2) . . . . ?
C5 C6 C7 C8 134.6(3) . . . . ?
C1 C6 C7 C8 -51.4(4) . . . . ?
C6 C7 C8 C9 -8.0(5) . . . . ?
C6 C7 C8 C15 170.4(3) . . . . ?
C7 C8 C9 C14 -39.4(4) . . . . ?
C15 C8 C9 C14 142.2(3) . . . . ?
C7 C8 C9 C10 142.0(3) . . . . ?
C15 C8 C9 C10 -36.5(4) . . . . ?
C14 C9 C10 C11 1.0(4) . . . . ?
C8 C9 C10 C11 179.7(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C9 0.8(4) . . . . ?
C10 C9 C14 C13 -1.2(4) . . . . ?
C8 C9 C14 C13 -179.9(2) . . . . ?
C7 C8 C15 C16 -57.0(4) . . . . ?
C9 C8 C15 C16 121.5(3) . . . . ?
C7 C8 C15 C20 124.0(3) . . . . ?
C9 C8 C15 C20 -57.5(4) . . . . ?
C20 C15 C16 C17 -1.4(4) . . . . ?
C8 C15 C16 C17 179.6(3) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 0.7(5) . . . . ?
C18 C19 C20 C15 -1.4(5) . . . . ?
C18 C19 C20 C21 -179.7(3) . . . . ?
C16 C15 C20 C19 1.8(4) . . . . ?
C8 C15 C20 C19 -179.2(3) . . . . ?
C16 C15 C20 C21 179.9(3) . . . . ?
C8 C15 C20 C21 -1.1(4) . . . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4

