# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_fzj238a1516
_database_code_depnum_ccdc_archive 'CCDC 2342656'
loop_
_audit_author_name
_audit_author_address
'GAVIN CHIT TSUI'
;Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2024-03-23 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 F5'
_chemical_formula_weight         299.26

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                   12.5210(10)
_cell_length_b                   6.0834(5)
_cell_length_c                   18.8326(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.427(2)
_cell_angle_gamma                90
_cell_volume                     1400.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    83
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3580
_exptl_absorpt_correction_T_max  0.7456
_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 D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15238
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.215
_diffrn_reflns_theta_max         25.233
_diffrn_reflns_theta_full        25.233
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2534
_reflns_number_gt                1770
_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       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_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)+(0.0766P)²+0.5685P] 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         2534
_refine_ls_number_parameters     238
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1747
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.1847(17) 0.146(3) 0.6278(6) 0.155(4) Uani 0.418(14) 1 d . U P A 1
F2 F 0.0801(6) 0.0750(9) 0.6260(4) 0.079(2) Uani 0.418(14) 1 d . U P A 1
F3 F 0.1907(15) 0.132(3) 0.7651(9) 0.112(4) Uani 0.418(14) 1 d . U P A 1
F4 F 0.0625(14) 0.369(3) 0.7531(8) 0.137(4) Uani 0.418(14) 1 d . U P A 1
F5 F 0.1667(9) 0.4760(13) 0.7503(5) 0.105(3) Uani 0.418(14) 1 d . U P A 1
F1' F 0.2260(3) 0.2558(13) 0.6390(3) 0.093(2) Uani 0.582(14) 1 d . U P A 2
F2' F 0.0356(12) 0.0934(17) 0.6360(5) 0.209(5) Uani 0.582(14) 1 d . U P A 2
F3' F 0.2178(9) 0.430(2) 0.7456(5) 0.184(4) Uani 0.582(14) 1 d . U P A 2
F4' F 0.1644(12) 0.100(2) 0.7607(7) 0.136(5) Uani 0.582(14) 1 d . U P A 2
F5' F 0.0312(9) 0.2848(18) 0.7422(7) 0.137(3) Uani 0.582(14) 1 d . U P A 2
C1 C 0.1352(3) 0.2883(7) 0.72812(19) 0.0922(13) Uani 1 1 d . . . . .
C2 C 0.1141(3) 0.2619(6) 0.64707(17) 0.0806(12) Uani 1 1 d . . . . .
C3 C 0.0646(2) 0.4518(4) 0.60230(13) 0.0671(11) Uani 1 1 d . . . . .
H3A H 0.114686 0.575235 0.612218 0.081 Uiso 1 1 calc R U . . .
H3B H -0.002065 0.493619 0.617153 0.081 Uiso 1 1 calc R U . . .
C4 C 0.03770(18) 0.4086(4) 0.52015(13) 0.0587(11) Uani 1 1 d . . . . .
H4A H -0.003373 0.270381 0.512142 0.070 Uiso 1 1 calc R U . . .
C5 C 0.13991(17) 0.3789(4) 0.48982(13) 0.0561(10) Uani 1 1 d . . . . .
C6 C 0.1592(2) 0.1838(4) 0.45744(13) 0.0621(11) Uani 1 1 d . . . . .
H6A H 0.109061 0.069694 0.454623 0.075 Uiso 1 1 calc R U . . .
C7 C 0.25094(19) 0.1534(4) 0.42914(13) 0.0612(10) Uani 1 1 d . . . . .
H7A H 0.261899 0.018990 0.408260 0.073 Uiso 1 1 calc R U . . .
C8 C 0.32711(17) 0.3201(4) 0.43132(12) 0.0558(10) Uani 1 1 d . . . . .
C9 C 0.30812(18) 0.5159(4) 0.46435(13) 0.0618(11) Uani 1 1 d . . . . .
H9A H 0.358190 0.630238 0.467233 0.074 Uiso 1 1 calc R U . . .
C10 C 0.21700(18) 0.5444(4) 0.49286(14) 0.0628(10) Uani 1 1 d . . . . .
H10A H 0.206706 0.677586 0.514695 0.075 Uiso 1 1 calc R U . . .
C11 C 0.42362(18) 0.2902(4) 0.39846(13) 0.0587(10) Uani 1 1 d . . . . .
C12 C 0.4810(2) 0.0947(4) 0.40626(15) 0.0717(11) Uani 1 1 d . . . . .
H12A H 0.458485 -0.019464 0.432453 0.086 Uiso 1 1 calc R U . . .
C13 C 0.5712(2) 0.0650(5) 0.37602(18) 0.0871(12) Uani 1 1 d . . . . .
H13A H 0.609044 -0.067569 0.382393 0.104 Uiso 1 1 calc R U . . .
C14 C 0.6048(2) 0.2302(6) 0.33672(17) 0.0861(12) Uani 1 1 d . . . . .
H14A H 0.665211 0.210270 0.316070 0.103 Uiso 1 1 calc R U . . .
C15 C 0.5490(2) 0.4246(6) 0.32802(16) 0.0837(12) Uani 1 1 d . . . . .
H15A H 0.571600 0.537267 0.301283 0.100 Uiso 1 1 calc R U . . .
C16 C 0.4593(2) 0.4552(5) 0.35857(15) 0.0731(11) Uani 1 1 d . . . . .
H16A H 0.422298 0.588752 0.352271 0.088 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 C2 1.245(10) . ?
F1 F2 1.37(3) . ?
F2 C2 1.248(7) . ?
F3 C1 1.288(15) . ?
F4 C1 1.214(15) . ?
F4 F5 1.47(2) . ?
F5 C1 1.250(9) . ?
F1' C2 1.443(5) . ?
F2' C2 1.404(9) . ?
F3' C1 1.331(8) . ?
F4' C1 1.315(13) . ?
F5' C1 1.383(11) . ?
C1 C2 1.501(5) . ?
C2 C3 1.485(4) . ?
C3 C4 1.534(3) . ?
C4 C5 1.520(3) . ?
C4 C4 1.548(5) 3_566 ?
C5 C6 1.379(3) . ?
C5 C10 1.388(3) . ?
C6 C7 1.378(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.388(3) . ?
C8 C11 1.483(3) . ?
C9 C10 1.372(3) . ?
C11 C12 1.381(4) . ?
C11 C16 1.384(3) . ?
C12 C13 1.381(4) . ?
C13 C14 1.367(4) . ?
C14 C15 1.366(4) . ?
C15 C16 1.380(4) . ?

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
C2 F1 F2 56.7(8) . . ?
C2 F2 F1 56.5(6) . . ?
C1 F4 F5 54.5(8) . . ?
C1 F5 F4 52.3(7) . . ?
F4 C1 F5 73.2(11) . . ?
F4 C1 F3 116.8(11) . . ?
F5 C1 F3 113.4(10) . . ?
F4' C1 F3' 109.0(8) . . ?
F4' C1 F5' 94.3(8) . . ?
F3' C1 F5' 132.6(10) . . ?
F4 C1 C2 117.0(7) . . ?
F5 C1 C2 114.3(5) . . ?
F3 C1 C2 115.3(8) . . ?
F4' C1 C2 110.6(7) . . ?
F3' C1 C2 106.1(5) . . ?
F5' C1 C2 103.1(6) . . ?
F1 C2 F2 66.8(12) . . ?
F2' C2 F1' 129.1(9) . . ?
F1 C2 C3 120.7(5) . . ?
F2 C2 C3 117.2(4) . . ?
F2' C2 C3 106.9(5) . . ?
F1' C2 C3 104.8(3) . . ?
F1 C2 C1 112.2(6) . . ?
F2 C2 C1 113.2(5) . . ?
F2' C2 C1 101.2(5) . . ?
F1' C2 C1 98.5(3) . . ?
C3 C2 C1 117.0(3) . . ?
C2 C3 C4 114.4(2) . . ?
C5 C4 C3 112.28(18) . . ?
C5 C4 C4 112.0(2) . 3_566 ?
C3 C4 C4 110.5(2) . 3_566 ?
C6 C5 C10 117.1(2) . . ?
C6 C5 C4 120.7(2) . . ?
C10 C5 C4 122.2(2) . . ?
C7 C6 C5 121.8(2) . . ?
C6 C7 C8 121.0(2) . . ?
C7 C8 C9 117.3(2) . . ?
C7 C8 C11 121.0(2) . . ?
C9 C8 C11 121.8(2) . . ?
C10 C9 C8 121.4(2) . . ?
C9 C10 C5 121.5(2) . . ?
C12 C11 C16 117.5(2) . . ?
C12 C11 C8 120.9(2) . . ?
C16 C11 C8 121.6(2) . . ?
C11 C12 C13 121.4(3) . . ?
C14 C13 C12 120.1(3) . . ?
C15 C14 C13 119.5(3) . . ?
C14 C15 C16 120.5(3) . . ?
C15 C16 C11 121.0(3) . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.052



