# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_wsf
_database_code_depnum_ccdc_archive 'CCDC 2129228'
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 F6 N2'
_chemical_formula_weight         446.39

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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6201(11)
_cell_length_b                   11.120(2)
_cell_length_c                   12.625(2)
_cell_angle_alpha                106.776(4)
_cell_angle_beta                 99.113(4)
_cell_angle_gamma                96.569(6)
_cell_volume                     996.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3488
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12636
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3488
_reflns_number_gt                3298
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0387P)²+0.4702P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3488
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F4 F 0.12882(12) -0.06454(8) 0.07468(8) 0.0407(2) Uani 1 1 d . . .
F5 F 0.26795(14) -0.04078(9) 0.24325(8) 0.0443(3) Uani 1 1 d . . .
N1 N 0.78370(14) 0.40629(10) 0.02129(9) 0.0212(2) Uani 1 1 d . . .
N2 N 0.75125(14) 0.56382(10) -0.05213(9) 0.0223(2) Uani 1 1 d . . .
C6 C 0.67148(17) 0.57994(13) 0.23109(11) 0.0236(3) Uani 1 1 d . . .
H6 H 0.6229 0.4946 0.2157 0.028 Uiso 1 1 calc R . .
F1 F 0.59726(15) 0.85534(10) 0.51361(9) 0.0579(3) Uani 1 1 d . . .
C18 C 0.66993(18) 0.25335(12) 0.11723(11) 0.0226(3) Uani 1 1 d . . .
F6 F 0.10795(14) 0.09652(9) 0.21189(10) 0.0541(3) Uani 1 1 d . . .
C17 C 0.82833(18) 0.33935(13) 0.10375(11) 0.0235(3) Uani 1 1 d . . .
H17A H 0.8808 0.4021 0.1766 0.028 Uiso 1 1 calc R . .
H17B H 0.9192 0.2884 0.0813 0.028 Uiso 1 1 calc R . .
C8 C 0.75950(16) 0.53083(12) 0.04088(11) 0.0210(3) Uani 1 1 d . . .
F2 F 0.88334(15) 0.89475(12) 0.54504(8) 0.0594(3) Uani 1 1 d . . .
C9 C 0.79005(17) 0.35971(12) -0.09119(11) 0.0225(3) Uani 1 1 d . . .
H9 H 0.8051 0.2778 -0.1296 0.027 Uiso 1 1 calc R . .
C4 C 0.81810(18) 0.74832(13) 0.17515(11) 0.0241(3) Uani 1 1 d . . .
H4 H 0.8684 0.7758 0.1219 0.029 Uiso 1 1 calc R . .
C7 C 0.66547(18) 0.66740(13) 0.33322(11) 0.0253(3) Uani 1 1 d . . .
H7 H 0.6141 0.6405 0.3864 0.030 Uiso 1 1 calc R . .
C3 C 0.81169(18) 0.83585(13) 0.27661(12) 0.0267(3) Uani 1 1 d . . .
H3 H 0.8577 0.9215 0.2917 0.032 Uiso 1 1 calc R . .
C10 C 0.77004(16) 0.45704(12) -0.13569(11) 0.0212(3) Uani 1 1 d . . .
C21 C 0.38451(19) 0.09809(12) 0.15043(12) 0.0257(3) Uani 1 1 d . . .
F3 F 0.73223(19) 1.00581(10) 0.46637(9) 0.0623(3) Uani 1 1 d . . .
C19 C 0.51336(19) 0.20784(13) 0.03559(12) 0.0272(3) Uani 1 1 d . . .
H19 H 0.5035 0.2294 -0.0307 0.033 Uiso 1 1 calc R . .
C2 C 0.73578(18) 0.79503(13) 0.35655(11) 0.0256(3) Uani 1 1 d . . .
C11 C 0.77002(17) 0.45831(13) -0.25181(11) 0.0226(3) Uani 1 1 d . . .
C5 C 0.75012(17) 0.61882(12) 0.15090(11) 0.0217(3) Uani 1 1 d . . .
C12 C 0.73542(19) 0.56569(13) -0.28232(12) 0.0283(3) Uani 1 1 d . . .
H12 H 0.7108 0.6359 -0.2292 0.034 Uiso 1 1 calc R . .
C22 C 0.5420(2) 0.14143(14) 0.23242(12) 0.0337(3) Uani 1 1 d . . .
H22 H 0.5520 0.1190 0.2983 0.040 Uiso 1 1 calc R . .
C16 C 0.80599(19) 0.35423(14) -0.33338(12) 0.0286(3) Uani 1 1 d . . .
H16 H 0.8291 0.2818 -0.3146 0.034 Uiso 1 1 calc R . .
C20 C 0.37104(19) 0.13027(13) 0.05196(12) 0.0286(3) Uani 1 1 d . . .
H20 H 0.2664 0.0998 -0.0034 0.034 Uiso 1 1 calc R . .
C23 C 0.6836(2) 0.21823(14) 0.21517(12) 0.0317(3) Uani 1 1 d . . .
H23 H 0.7894 0.2468 0.2697 0.038 Uiso 1 1 calc R . .
C1 C 0.7353(2) 0.88746(15) 0.46893(13) 0.0341(3) Uani 1 1 d . . .
C24 C 0.2247(2) 0.02306(13) 0.17037(13) 0.0324(3) Uani 1 1 d . . .
C15 C 0.8076(2) 0.35764(16) -0.44219(13) 0.0368(4) Uani 1 1 d . . .
H15 H 0.8316 0.2876 -0.4958 0.044 Uiso 1 1 calc R . .
C13 C 0.7375(2) 0.56854(15) -0.39112(13) 0.0374(4) Uani 1 1 d . . .
H13 H 0.7143 0.6406 -0.4105 0.045 Uiso 1 1 calc R . .
C14 C 0.7738(2) 0.46480(17) -0.47132(13) 0.0403(4) Uani 1 1 d . . .
H14 H 0.7754 0.4672 -0.5442 0.048 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
F4 C24 1.3492(18) . ?
F5 C24 1.3392(18) . ?
N1 C8 1.3742(17) . ?
N1 C9 1.3747(17) . ?
N1 C17 1.4652(16) . ?
N2 C8 1.3221(17) . ?
N2 C10 1.3809(17) . ?
C6 C7 1.3840(19) . ?
C6 C5 1.3988(19) . ?
F1 C1 1.3307(18) . ?
C18 C19 1.3831(19) . ?
C18 C23 1.3927(19) . ?
C18 C17 1.5150(18) . ?
F6 C24 1.3418(18) . ?
C8 C5 1.4678(18) . ?
F2 C1 1.3390(19) . ?
C9 C10 1.3682(19) . ?
C4 C3 1.379(2) . ?
C4 C5 1.4002(19) . ?
C7 C2 1.387(2) . ?
C3 C2 1.396(2) . ?
C10 C11 1.4701(18) . ?
C21 C20 1.382(2) . ?
C21 C22 1.389(2) . ?
C21 C24 1.493(2) . ?
F3 C1 1.3286(19) . ?
C19 C20 1.387(2) . ?
C2 C1 1.493(2) . ?
C11 C16 1.396(2) . ?
C11 C12 1.396(2) . ?
C12 C13 1.386(2) . ?
C22 C23 1.383(2) . ?
C16 C15 1.387(2) . ?
C15 C14 1.384(2) . ?
C13 C14 1.386(2) . ?

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
C8 N1 C9 106.45(11) . . ?
C8 N1 C17 128.43(11) . . ?
C9 N1 C17 124.23(11) . . ?
C8 N2 C10 106.06(11) . . ?
C7 C6 C5 120.52(12) . . ?
C19 C18 C23 118.98(13) . . ?
C19 C18 C17 122.44(12) . . ?
C23 C18 C17 118.59(12) . . ?
N1 C17 C18 114.67(11) . . ?
N2 C8 N1 111.24(11) . . ?
N2 C8 C5 123.55(12) . . ?
N1 C8 C5 125.18(11) . . ?
C10 C9 N1 106.82(11) . . ?
C3 C4 C5 121.11(12) . . ?
C6 C7 C2 120.19(13) . . ?
C4 C3 C2 119.59(13) . . ?
C9 C10 N2 109.43(11) . . ?
C9 C10 C11 128.93(12) . . ?
N2 C10 C11 121.63(12) . . ?
C20 C21 C22 120.08(13) . . ?
C20 C21 C24 119.25(13) . . ?
C22 C21 C24 120.57(13) . . ?
C18 C19 C20 120.47(13) . . ?
C7 C2 C3 120.03(13) . . ?
C7 C2 C1 119.62(13) . . ?
C3 C2 C1 120.32(13) . . ?
C16 C11 C12 118.50(13) . . ?
C16 C11 C10 121.45(12) . . ?
C12 C11 C10 120.04(12) . . ?
C6 C5 C4 118.53(12) . . ?
C6 C5 C8 123.07(12) . . ?
C4 C5 C8 118.37(12) . . ?
C13 C12 C11 120.51(13) . . ?
C23 C22 C21 119.43(13) . . ?
C15 C16 C11 120.70(14) . . ?
C21 C20 C19 120.11(13) . . ?
C22 C23 C18 120.91(14) . . ?
F3 C1 F1 107.34(13) . . ?
F3 C1 F2 105.50(13) . . ?
F1 C1 F2 105.38(13) . . ?
F3 C1 C2 113.34(13) . . ?
F1 C1 C2 112.99(12) . . ?
F2 C1 C2 111.69(13) . . ?
F5 C24 F6 106.19(12) . . ?
F5 C24 F4 106.15(11) . . ?
F6 C24 F4 105.61(13) . . ?
F5 C24 C21 113.36(13) . . ?
F6 C24 C21 112.49(12) . . ?
F4 C24 C21 112.44(12) . . ?
C14 C15 C16 120.27(14) . . ?
C12 C13 C14 120.49(14) . . ?
C15 C14 C13 119.52(14) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046

