# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_dwb23002
_database_code_depnum_ccdc_archive 'CCDC 2417550'
loop_
_audit_author_name
_audit_author_address
'Adrian Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2025-01-16 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_audit_creation_date             2023-02-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H7 F13 N2'
_chemical_formula_sum            'C11 H7 F13 N2'
_chemical_formula_weight         414.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H8 F13 N2'
_chemical_oxdiff_usercomment     'Joshua Lai JL-032'
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'
N N 0.0311 0.0180 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   23.8130(4)
_cell_length_b                   5.42950(10)
_cell_length_c                   11.1728(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.196(2)
_cell_angle_gamma                90
_cell_volume                     1440.69(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4935
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      75.9790
_cell_measurement_theta_min      3.7010
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.501
_exptl_absorpt_coefficient_mu    2.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 0 0.1631
-1 0 2 0.0523
1 0 -2 0.0650
1 1 -2 0.1463
-1 0 0 0.0229
1 0 0 0.0210
-2 1 -2 0.1365
-2 1 2 0.1267

_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0038 -0.9991 0.0034 -0.0551 -0.2833 -0.0353
-1.0150 0.0008 1.9986 -0.0247 -0.0195 0.2776
1.0150 -0.0008 -1.9986 0.0247 0.0195 -0.2776
1.0102 0.9987 -2.0005 0.1391 0.2774 -0.2492
-0.9990 -0.0004 -0.0015 -0.0592 0.0255 0.0070
0.9990 0.0004 0.0015 0.0592 -0.0255 -0.0070
-1.9867 0.9974 -2.0049 -0.0386 0.3537 -0.2282
-2.0188 0.9999 1.9952 0.0304 0.2638 0.3129

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8586
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.630
_diffrn_reflns_theta_min         3.722
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -22.00   0.50    4.00    --  -48.70 122.00 -72.00  124
  2  ω   -119.00 -57.00   0.50    4.00    --  -48.70-151.00  44.00  124
  3  ω     55.00  89.00   0.50    4.00    --   48.70-122.00-154.00   68
  4  ω    136.00 176.00   0.50   16.00    --  107.75 122.00 -72.00   80
  5  ω     89.00 125.00   0.50   16.00    --  107.75-151.00  44.00   72
  6  ω     50.00  75.00   0.50   16.00    --  107.75-122.00-154.00   50
  7  ω    102.00 131.00   0.50   16.00    --  107.75 122.00 -72.00   58
  8  ω   -116.00 -74.00   0.50    4.00    --  -48.70-125.00-120.00   84
  9  ω   -110.00 -82.00   0.50    4.00    --  -48.70-125.00 -90.00   56
 10  ω   -103.00 -41.00   0.50    4.00    --  -48.70 -37.00  60.00  124
 11  ω   -120.00 -50.00   0.50    4.00    --  -48.70 -57.00-180.00  140
 12  ω     38.00 106.00   0.50   16.00    --  107.75 -99.00-150.00  136
 13  ω     95.00 163.00   0.50   16.00    --  107.75  37.00-180.00  136
 14  ω     95.00 124.00   0.50   16.00    --  107.75  37.00  30.00   58
 15  ω     41.00 112.00   0.50   16.00    --  107.75 -57.00   0.00  142
 16  ω    128.00 153.00   0.50   16.00    --  107.75  37.00  30.00   50
 17  ω     75.00 102.00   0.50   16.00    --  107.75 -99.00 -90.00   54
 18  ω     37.00 118.00   0.50   16.00    --  107.75 -37.00 -30.00  162
 19  ω     88.00 134.00   0.50   16.00    --  107.75 151.00  88.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0592145000
_diffrn_orient_matrix_UB_12      0.1146965000
_diffrn_orient_matrix_UB_13      0.0176452000
_diffrn_orient_matrix_UB_21      -0.0255581000
_diffrn_orient_matrix_UB_22      0.2578131000
_diffrn_orient_matrix_UB_23      -0.0228394000
_diffrn_orient_matrix_UB_31      -0.0072272000
_diffrn_orient_matrix_UB_32      0.0285778000
_diffrn_orient_matrix_UB_33      0.1351962000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2482
_reflns_number_total             2882
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.058
_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)+(0.0506P)²+0.9734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C2(H2)
;
_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
F6 F 0.73272(5) 0.7524(2) 0.58190(10) 0.0307(3) Uani 1 1 d . . . . .
F5 F 0.68124(5) 0.8178(2) 0.41567(10) 0.0317(3) Uani 1 1 d . . . . .
F1 F 0.79009(5) 0.8164(2) 0.35032(12) 0.0370(3) Uani 1 1 d . . . . .
F4 F 0.75240(5) 0.2689(2) 0.48611(12) 0.0356(3) Uani 1 1 d . . . . .
F2 F 0.83017(5) 0.6118(3) 0.50037(10) 0.0367(3) Uani 1 1 d . . . . .
F3 F 0.71438(5) 0.4133(3) 0.31708(10) 0.0382(3) Uani 1 1 d . . . . .
F7 F 0.63142(5) 0.3426(2) 0.46014(11) 0.0386(3) Uani 1 1 d . . . . .
F10 F 0.62634(5) 0.8559(2) 0.64681(12) 0.0402(3) Uani 1 1 d . . . . .
F8 F 0.67350(5) 0.3750(2) 0.63914(11) 0.0382(3) Uani 1 1 d . . . . .
F12 F 0.54256(5) 0.3328(3) 0.60139(12) 0.0415(3) Uani 1 1 d . . . . .
F9 F 0.57607(5) 0.7560(3) 0.48326(11) 0.0412(3) Uani 1 1 d . . . . .
F11 F 0.51855(6) 0.6827(3) 0.67024(14) 0.0512(4) Uani 1 1 d . . . . .
F13 F 0.58459(6) 0.4736(3) 0.76322(11) 0.0469(4) Uani 1 1 d . . . . .
N1 N 0.91600(6) 0.3958(3) 0.19983(13) 0.0225(3) Uani 1 1 d . . . . .
N2 N 0.94418(7) 0.2582(3) 0.02744(14) 0.0305(4) Uani 1 1 d . . . . .
C1 C 0.94434(8) 0.1796(3) 0.22511(16) 0.0241(4) Uani 1 1 d . . . . .
H1 H 0.950789 0.103048 0.301335 0.029 Uiso 1 1 calc R U . . .
C8 C 0.70250(7) 0.6425(3) 0.49083(15) 0.0209(4) Uani 1 1 d . . . . .
C3 C 0.96125(8) 0.0977(3) 0.11851(16) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.981930 -0.049493 0.108238 0.030 Uiso 1 1 calc R U . . .
C7 C 0.74184(8) 0.4756(3) 0.42146(16) 0.0233(4) Uani 1 1 d . . . . .
C6 C 0.79931(7) 0.5856(3) 0.39407(16) 0.0236(4) Uani 1 1 d . . . . .
C9 C 0.65288(7) 0.5017(3) 0.54306(15) 0.0231(4) Uani 1 1 d . . . . .
C4 C 0.88718(8) 0.5479(3) 0.28358(17) 0.0260(4) Uani 1 1 d . . . . .
H4A H 0.880797 0.714515 0.249274 0.031 Uiso 1 1 calc R U . . .
H4B H 0.910972 0.564423 0.359597 0.031 Uiso 1 1 calc R U . . .
C5 C 0.83074(8) 0.4319(3) 0.30872(17) 0.0263(4) Uani 1 1 d . . . . .
H5A H 0.807391 0.413169 0.232240 0.032 Uiso 1 1 calc R U . . .
H5B H 0.837392 0.265759 0.343393 0.032 Uiso 1 1 calc R U . . .
C2 C 0.91729(8) 0.4337(4) 0.08043(17) 0.0296(4) Uani 1 1 d . . . . .
H2 H 0.900624 0.571842 0.039495 0.036 Uiso 1 1 calc R U . . .
C10 C 0.60439(8) 0.6676(4) 0.58105(17) 0.0268(4) Uani 1 1 d . . . . .
C11 C 0.56173(8) 0.5337(4) 0.65683(17) 0.0312(4) Uani 1 1 d . . . . .


_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
F6 C8 1.342(2) . ?
F5 C8 1.343(2) . ?
F1 C6 1.357(2) . ?
F4 C7 1.348(2) . ?
F2 C6 1.358(2) . ?
F3 C7 1.338(2) . ?
F7 C9 1.340(2) . ?
F10 C10 1.342(2) . ?
F8 C9 1.338(2) . ?
F12 C11 1.319(2) . ?
F9 C10 1.331(2) . ?
F11 C11 1.325(2) . ?
F13 C11 1.312(2) . ?
N1 C1 1.373(2) . ?
N1 C4 1.457(2) . ?
N1 C2 1.352(2) . ?
N2 C3 1.378(2) . ?
N2 C2 1.313(3) . ?
C1 H1 0.9500 . ?
C1 C3 1.360(3) . ?
C8 C7 1.551(2) . ?
C8 C9 1.556(2) . ?
C3 H3 0.9500 . ?
C7 C6 1.544(2) . ?
C6 C5 1.507(2) . ?
C9 C10 1.548(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.529(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C2 H2 0.9500 . ?
C10 C11 1.550(3) . ?

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
C1 N1 C4 126.87(15) . . ?
C2 N1 C1 106.67(15) . . ?
C2 N1 C4 126.37(16) . . ?
C2 N2 C3 104.68(15) . . ?
N1 C1 H1 127.1 . . ?
C3 C1 N1 105.79(16) . . ?
C3 C1 H1 127.1 . . ?
F6 C8 F5 108.39(14) . . ?
F6 C8 C7 109.17(14) . . ?
F6 C8 C9 108.29(14) . . ?
F5 C8 C7 108.38(14) . . ?
F5 C8 C9 108.72(14) . . ?
C7 C8 C9 113.77(14) . . ?
N2 C3 H3 124.8 . . ?
C1 C3 N2 110.46(16) . . ?
C1 C3 H3 124.8 . . ?
F4 C7 C8 108.32(14) . . ?
F4 C7 C6 107.15(15) . . ?
F3 C7 F4 108.46(15) . . ?
F3 C7 C8 107.97(14) . . ?
F3 C7 C6 107.98(14) . . ?
C6 C7 C8 116.72(14) . . ?
F1 C6 F2 106.31(15) . . ?
F1 C6 C7 107.83(14) . . ?
F1 C6 C5 110.98(15) . . ?
F2 C6 C7 107.35(14) . . ?
F2 C6 C5 110.46(15) . . ?
C5 C6 C7 113.57(14) . . ?
F7 C9 C8 108.61(13) . . ?
F7 C9 C10 108.07(15) . . ?
F8 C9 F7 108.82(15) . . ?
F8 C9 C8 108.03(14) . . ?
F8 C9 C10 108.44(14) . . ?
C10 C9 C8 114.75(15) . . ?
N1 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
N1 C4 C5 110.28(15) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C6 C5 C4 111.87(15) . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C2 H2 123.8 . . ?
N2 C2 N1 112.41(17) . . ?
N2 C2 H2 123.8 . . ?
F10 C10 C9 108.96(15) . . ?
F10 C10 C11 107.62(15) . . ?
F9 C10 F10 109.18(16) . . ?
F9 C10 C9 109.15(15) . . ?
F9 C10 C11 107.72(15) . . ?
C9 C10 C11 114.12(16) . . ?
F12 C11 F11 108.25(17) . . ?
F12 C11 C10 110.44(15) . . ?
F11 C11 C10 108.69(17) . . ?
F13 C11 F12 109.01(18) . . ?
F13 C11 F11 108.87(16) . . ?
F13 C11 C10 111.50(16) . . ?

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
F6 C8 C7 F4 76.59(17) . . . . ?
F6 C8 C7 F3 -166.15(14) . . . . ?
F6 C8 C7 C6 -44.4(2) . . . . ?
F6 C8 C9 F7 -164.33(14) . . . . ?
F6 C8 C9 F8 -46.46(18) . . . . ?
F6 C8 C9 C10 74.63(18) . . . . ?
F5 C8 C7 F4 -165.54(14) . . . . ?
F5 C8 C7 F3 -48.28(18) . . . . ?
F5 C8 C7 C6 73.50(19) . . . . ?
F5 C8 C9 F7 78.10(17) . . . . ?
F5 C8 C9 F8 -164.03(14) . . . . ?
F5 C8 C9 C10 -42.9(2) . . . . ?
F1 C6 C5 C4 58.0(2) . . . . ?
F4 C7 C6 F1 -168.12(13) . . . . ?
F4 C7 C6 F2 -53.94(18) . . . . ?
F4 C7 C6 C5 68.47(19) . . . . ?
F2 C6 C5 C4 -59.6(2) . . . . ?
F3 C7 C6 F1 75.23(18) . . . . ?
F3 C7 C6 F2 -170.59(14) . . . . ?
F3 C7 C6 C5 -48.2(2) . . . . ?
F7 C9 C10 F10 -168.77(15) . . . . ?
F7 C9 C10 F9 -49.6(2) . . . . ?
F7 C9 C10 C11 70.93(19) . . . . ?
F10 C10 C11 F12 -174.16(16) . . . . ?
F10 C10 C11 F11 67.2(2) . . . . ?
F10 C10 C11 F13 -52.8(2) . . . . ?
F8 C9 C10 F10 73.43(19) . . . . ?
F8 C9 C10 F9 -167.43(15) . . . . ?
F8 C9 C10 C11 -46.9(2) . . . . ?
F9 C10 C11 F12 68.2(2) . . . . ?
F9 C10 C11 F11 -50.4(2) . . . . ?
F9 C10 C11 F13 -170.39(17) . . . . ?
N1 C1 C3 N2 0.1(2) . . . . ?
N1 C4 C5 C6 -179.36(15) . . . . ?
C1 N1 C4 C5 -76.7(2) . . . . ?
C1 N1 C2 N2 0.1(2) . . . . ?
C8 C7 C6 F1 -46.5(2) . . . . ?
C8 C7 C6 F2 67.64(19) . . . . ?
C8 C7 C6 C5 -169.96(15) . . . . ?
C8 C9 C10 F10 -47.4(2) . . . . ?
C8 C9 C10 F9 71.7(2) . . . . ?
C8 C9 C10 C11 -167.73(15) . . . . ?
C3 N2 C2 N1 0.0(2) . . . . ?
C7 C8 C9 F7 -42.8(2) . . . . ?
C7 C8 C9 F8 75.11(18) . . . . ?
C7 C8 C9 C10 -163.80(15) . . . . ?
C7 C6 C5 C4 179.71(15) . . . . ?
C9 C8 C7 F4 -44.49(19) . . . . ?
C9 C8 C7 F3 72.77(18) . . . . ?
C9 C8 C7 C6 -165.45(15) . . . . ?
C9 C10 C11 F12 -53.1(2) . . . . ?
C9 C10 C11 F11 -171.73(16) . . . . ?
C9 C10 C11 F13 68.3(2) . . . . ?
C4 N1 C1 C3 176.53(16) . . . . ?
C4 N1 C2 N2 -176.57(17) . . . . ?
C2 N1 C1 C3 -0.1(2) . . . . ?
C2 N1 C4 C5 99.3(2) . . . . ?
C2 N2 C3 C1 0.0(2) . . . . ?

_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.742
####################################################################### 
# 
# 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_dwb23011
_database_code_depnum_ccdc_archive 'CCDC 2417551'
loop_
_audit_author_name
_audit_author_address
'Adrian Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2025-01-16 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_audit_creation_date             2023-06-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H7 F17 N2'
_chemical_formula_sum            'C13 H7 F17 N2'
_chemical_formula_weight         514.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H7 F17 N2'
_chemical_oxdiff_usercomment     'Joshua Lai JL-096-1'
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'
N N 0.0311 0.0180 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   30.1835(5)
_cell_length_b                   5.56120(10)
_cell_length_c                   10.3336(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.232(2)
_cell_angle_gamma                90
_cell_volume                     1731.80(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8505
_cell_measurement_temperature    110.00(14)
_cell_measurement_theta_max      76.5770
_cell_measurement_theta_min      8.0890
_shelx_estimated_absorpt_T_max   0.754
_shelx_estimated_absorpt_T_min   0.410
_exptl_absorpt_coefficient_mu    2.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 1 0.1193
-1 -2 2 0.1475
1 0 -1 0.1242
-1 0 0 0.0258
1 0 0 0.1016
-1 0 1 0.0898

_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9944 0.9991 1.0012 0.1960 0.1771 0.1947
-0.9665 -1.9984 1.9999 -0.4557 -0.3601 0.2431
0.9890 -0.0001 -1.0003 0.0091 0.0116 -0.1542
-0.9993 -0.0003 0.0010 -0.0274 0.0402 0.0155
0.9993 0.0003 -0.0010 0.0274 -0.0402 -0.0155
-0.9890 0.0001 1.0003 -0.0091 -0.0116 0.1542

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13768
_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         77.000
_diffrn_reflns_theta_min         4.402
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(14)
_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   -118.00 -41.00   0.50    3.00    --  -47.17-178.00  30.00  154
  2  ω   -118.00 -32.00   0.50    3.00    --  -47.17 -57.00  30.00  172
  3  ω    -54.00 -18.00   0.50    3.00    --  -47.17  37.00-180.00   72
  4  ω     27.00  53.00   0.50    3.00    --   47.17 -37.00 -60.00   52
  5  ω     40.00  93.00   0.50    3.00    --   47.17  37.00 -90.00  106
  6  ω    -24.00  21.00   0.50    3.00    --   47.17 -37.00 -60.00   90
  7  ω    -18.00   8.00   0.50    3.00    --   47.17 -57.00-120.00   52
  8  ω     13.00  62.00   0.50    3.00    --   47.17 -57.00-120.00   98
  9  ω     93.00 175.00   0.50   12.00    --  107.75  57.00 -90.00  164
 10  ω    135.00 177.00   0.50   12.00    --  107.75  19.00  90.00   84
 11  ω     60.00 104.00   0.50   12.00    --  107.75-125.00  90.00   88
 12  ω     39.00  90.00   0.50   12.00    --  107.75 -99.00 150.00  102
 13  ω     39.00  65.00   0.50   12.00    --  107.75 -77.00-150.00   52
 14  ω     94.00 177.00   0.50   12.00    --  107.75  57.00-120.00  166
 15  ω     39.00 108.00   0.50   12.00    --  107.75 -19.00  90.00  138
 16  ω     61.00 106.00   0.50   12.00    --  107.75 -99.00 120.00   90
 17  ω     43.00 119.00   0.50   12.00    --  107.75 -57.00 -60.00  152
 18  ω     75.00 102.00   0.50   12.00    --  107.75 -99.00 -30.00   54
 19  ω     37.00  69.00   0.50   12.00    --  107.75 -99.00 -30.00   64
 20  ω     43.00  77.00   0.50   12.00    --  107.75-125.00 -30.00   68
 21  ω     71.00 109.00   0.50   12.00    --  107.75-125.00  60.00   76
 22  ω     95.00 121.00   0.50   12.00    --  107.75  19.00  90.00   52
 23  ω     49.00 102.00   0.50   12.00    --  107.75 -99.00-150.00  106
 24  ω    100.00 125.00   0.50   12.00    --  107.75 -77.00-150.00   50
 25  ω     38.00 147.00   0.50   12.00    --  107.75   0.00  60.00  218
 26  ω     69.00 105.00   0.50   12.00    --  107.75 -99.00-120.00   72
 27  ω     38.00  70.00   0.50   12.00    --  107.75 -99.00  90.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0273385000
_diffrn_orient_matrix_UB_12      0.2327380000
_diffrn_orient_matrix_UB_13      0.0179183000
_diffrn_orient_matrix_UB_21      -0.0403717000
_diffrn_orient_matrix_UB_22      0.1482118000
_diffrn_orient_matrix_UB_23      -0.0514780000
_diffrn_orient_matrix_UB_31      -0.0154004000
_diffrn_orient_matrix_UB_32      0.0248908000
_diffrn_orient_matrix_UB_33      0.1389669000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3319
_reflns_number_total             3550
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0809
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1171P)²+4.9319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2490
_refine_ls_wR_factor_ref         0.2506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C1(H1)
;
_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 0.85035(8) 0.5619(6) 0.6213(2) 0.0455(7) Uani 1 1 d . . . . .
F1 F 0.83309(8) 0.2277(4) 0.7142(3) 0.0436(7) Uani 1 1 d . . . . .
F3 F 0.76605(8) 0.4781(6) 0.8343(2) 0.0499(8) Uani 1 1 d . . . . .
F4 F 0.78087(9) 0.7853(4) 0.7136(3) 0.0480(7) Uani 1 1 d . . . . .
F7 F 0.69196(9) 0.6168(6) 0.7077(3) 0.0534(8) Uani 1 1 d . . . . .
F11 F 0.61765(9) 0.7024(6) 0.5620(3) 0.0560(9) Uani 1 1 d . . . . .
F8 F 0.71086(9) 0.7639(5) 0.5252(3) 0.0524(8) Uani 1 1 d . . . . .
F12 F 0.63809(9) 0.6730(6) 0.3659(3) 0.0515(8) Uani 1 1 d . . . . .
F17 F 0.53947(9) 0.7251(6) 0.4089(3) 0.0533(8) Uani 1 1 d . . . . .
F15 F 0.56170(9) 0.5668(6) 0.2353(3) 0.0535(8) Uani 1 1 d . . . . .
F10 F 0.68796(9) 0.3040(6) 0.4177(3) 0.0577(9) Uani 1 1 d . . . . .
F6 F 0.77265(9) 0.4579(7) 0.4999(3) 0.0615(10) Uani 1 1 d . . . . .
F9 F 0.65739(9) 0.2329(5) 0.5990(4) 0.0611(10) Uani 1 1 d . . . . .
F5 F 0.74603(10) 0.2067(5) 0.6352(4) 0.0652(11) Uani 1 1 d . . . . .
F14 F 0.59982(10) 0.2011(5) 0.3642(4) 0.0622(9) Uani 1 1 d . . . . .
F16 F 0.51424(9) 0.3844(6) 0.3455(3) 0.0595(9) Uani 1 1 d . . . . .
N2 N 0.92972(10) 0.5350(6) 0.9704(3) 0.0249(6) Uani 1 1 d . . . . .
F13 F 0.57019(10) 0.3130(8) 0.5422(3) 0.0698(11) Uani 1 1 d . . . . .
N1 N 0.95415(11) 0.5296(6) 1.1766(3) 0.0318(7) Uani 1 1 d . . . . .
C6 C 0.83175(13) 0.4705(7) 0.7272(4) 0.0270(8) Uani 1 1 d . . . . .
C7 C 0.78237(13) 0.5451(7) 0.7222(4) 0.0272(8) Uani 1 1 d . . . . .
C4 C 0.90565(13) 0.4625(7) 0.8513(3) 0.0287(8) Uani 1 1 d . . . . .
H4A H 0.906318 0.285053 0.843710 0.034 Uiso 1 1 calc R U . . .
H4B H 0.920302 0.530974 0.776290 0.034 Uiso 1 1 calc R U . . .
C9 C 0.70598(13) 0.5613(7) 0.5923(4) 0.0280(8) Uani 1 1 d . . . . .
C2 C 0.95527(12) 0.7385(7) 0.9903(4) 0.0280(8) Uani 1 1 d . . . . .
H2 H 0.961268 0.858828 0.928387 0.034 Uiso 1 1 calc R U . . .
C3 C 0.93030(13) 0.4180(7) 1.0849(4) 0.0308(8) Uani 1 1 d . . . . .
H3 H 0.915112 0.271060 1.097754 0.037 Uiso 1 1 calc R U . . .
C5 C 0.85751(13) 0.5480(7) 0.8487(4) 0.0303(8) Uani 1 1 d . . . . .
H5A H 0.843150 0.482295 0.924888 0.036 Uiso 1 1 calc R U . . .
H5B H 0.856944 0.725665 0.854814 0.036 Uiso 1 1 calc R U . . .
C1 C 0.97017(13) 0.7312(8) 1.1174(4) 0.0302(8) Uani 1 1 d . . . . .
H1 H 0.988901 0.848393 1.159098 0.036 Uiso 1 1 calc R U . . .
C10 C 0.67002(13) 0.4044(7) 0.5197(4) 0.0298(8) Uani 1 1 d . . . . .
C11 C 0.62833(13) 0.5477(7) 0.4698(4) 0.0295(8) Uani 1 1 d . . . . .
C8 C 0.75210(13) 0.4378(7) 0.6111(4) 0.0304(8) Uani 1 1 d . . . . .
C12 C 0.58728(14) 0.3898(8) 0.4341(4) 0.0369(9) Uani 1 1 d . . . . .
C13 C 0.54991(14) 0.5206(9) 0.3531(4) 0.0381(9) Uani 1 1 d . . . . .


_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 C6 1.356(4) . ?
F1 C6 1.358(4) . ?
F3 C7 1.337(4) . ?
F4 C7 1.339(4) . ?
F7 C9 1.325(5) . ?
F11 C11 1.336(5) . ?
F8 C9 1.335(5) . ?
F12 C11 1.327(5) . ?
F17 C13 1.321(6) . ?
F15 C13 1.312(5) . ?
F10 C10 1.335(5) . ?
F6 C8 1.341(5) . ?
F9 C10 1.327(5) . ?
F5 C8 1.323(5) . ?
F14 C12 1.341(6) . ?
F16 C13 1.315(5) . ?
N2 C4 1.451(4) . ?
N2 C2 1.378(5) . ?
N2 C3 1.349(5) . ?
F13 C12 1.327(5) . ?
N1 C3 1.313(5) . ?
N1 C1 1.378(5) . ?
C6 C7 1.545(5) . ?
C6 C5 1.503(5) . ?
C7 C8 1.546(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.528(5) . ?
C9 C10 1.552(5) . ?
C9 C8 1.555(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.365(5) . ?
C3 H3 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C1 H1 0.9500 . ?
C10 C11 1.553(5) . ?
C11 C12 1.546(6) . ?
C12 C13 1.547(6) . ?

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 N2 C4 127.1(3) . . ?
C3 N2 C4 126.2(3) . . ?
C3 N2 C2 106.6(3) . . ?
C3 N1 C1 104.8(3) . . ?
F2 C6 F1 106.1(3) . . ?
F2 C6 C7 108.4(3) . . ?
F2 C6 C5 110.4(3) . . ?
F1 C6 C7 107.3(3) . . ?
F1 C6 C5 110.5(3) . . ?
C5 C6 C7 113.8(3) . . ?
F3 C7 F4 108.8(3) . . ?
F3 C7 C6 107.4(3) . . ?
F3 C7 C8 107.7(3) . . ?
F4 C7 C6 107.4(3) . . ?
F4 C7 C8 108.6(3) . . ?
C6 C7 C8 116.7(3) . . ?
N2 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
N2 C4 C5 111.0(3) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
F7 C9 F8 108.7(3) . . ?
F7 C9 C10 108.4(3) . . ?
F7 C9 C8 108.6(3) . . ?
F8 C9 C10 108.6(3) . . ?
F8 C9 C8 108.3(3) . . ?
C10 C9 C8 114.1(3) . . ?
N2 C2 H2 127.2 . . ?
C1 C2 N2 105.7(3) . . ?
C1 C2 H2 127.2 . . ?
N2 C3 H3 123.7 . . ?
N1 C3 N2 112.6(4) . . ?
N1 C3 H3 123.7 . . ?
C6 C5 C4 111.9(3) . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C1 H1 124.8 . . ?
C2 C1 N1 110.3(3) . . ?
C2 C1 H1 124.8 . . ?
F10 C10 C9 108.2(3) . . ?
F10 C10 C11 108.0(3) . . ?
F9 C10 F10 109.3(4) . . ?
F9 C10 C9 108.9(3) . . ?
F9 C10 C11 108.6(3) . . ?
C9 C10 C11 113.8(3) . . ?
F11 C11 C10 108.5(3) . . ?
F11 C11 C12 108.2(3) . . ?
F12 C11 F11 108.2(4) . . ?
F12 C11 C10 109.0(3) . . ?
F12 C11 C12 108.5(3) . . ?
C12 C11 C10 114.3(3) . . ?
F6 C8 C7 108.8(3) . . ?
F6 C8 C9 108.0(3) . . ?
F5 C8 F6 108.5(4) . . ?
F5 C8 C7 108.5(3) . . ?
F5 C8 C9 108.7(3) . . ?
C7 C8 C9 114.2(3) . . ?
F14 C12 C11 109.0(3) . . ?
F14 C12 C13 107.2(4) . . ?
F13 C12 F14 109.6(4) . . ?
F13 C12 C11 109.1(4) . . ?
F13 C12 C13 107.5(3) . . ?
C11 C12 C13 114.3(4) . . ?
F17 C13 C12 110.7(4) . . ?
F15 C13 F17 108.6(4) . . ?
F15 C13 F16 108.7(4) . . ?
F15 C13 C12 111.5(4) . . ?
F16 C13 F17 107.9(4) . . ?
F16 C13 C12 109.4(4) . . ?

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
F2 C6 C7 F3 -172.8(3) . . . . ?
F2 C6 C7 F4 -55.9(4) . . . . ?
F2 C6 C7 C8 66.2(4) . . . . ?
F2 C6 C5 C4 -60.0(4) . . . . ?
F1 C6 C7 F3 73.0(4) . . . . ?
F1 C6 C7 F4 -170.1(3) . . . . ?
F1 C6 C7 C8 -48.0(4) . . . . ?
F1 C6 C5 C4 57.1(4) . . . . ?
F3 C7 C8 F6 -166.9(3) . . . . ?
F3 C7 C8 F5 -49.1(4) . . . . ?
F3 C7 C8 C9 72.3(4) . . . . ?
F4 C7 C8 F6 75.3(4) . . . . ?
F4 C7 C8 F5 -166.8(3) . . . . ?
F4 C7 C8 C9 -45.4(5) . . . . ?
F7 C9 C10 F10 -166.1(3) . . . . ?
F7 C9 C10 F9 -47.4(4) . . . . ?
F7 C9 C10 C11 73.8(4) . . . . ?
F7 C9 C8 F6 -158.8(3) . . . . ?
F7 C9 C8 F5 83.6(4) . . . . ?
F7 C9 C8 C7 -37.7(5) . . . . ?
F11 C11 C12 F14 -166.4(3) . . . . ?
F11 C11 C12 F13 -46.7(5) . . . . ?
F11 C11 C12 C13 73.6(5) . . . . ?
F8 C9 C10 F10 76.0(4) . . . . ?
F8 C9 C10 F9 -165.3(3) . . . . ?
F8 C9 C10 C11 -44.1(4) . . . . ?
F8 C9 C8 F6 -40.9(4) . . . . ?
F8 C9 C8 F5 -158.5(4) . . . . ?
F8 C9 C8 C7 80.2(4) . . . . ?
F12 C11 C12 F14 76.4(4) . . . . ?
F12 C11 C12 F13 -163.9(4) . . . . ?
F12 C11 C12 C13 -43.5(5) . . . . ?
F10 C10 C11 F11 -162.3(3) . . . . ?
F10 C10 C11 F12 -44.7(4) . . . . ?
F10 C10 C11 C12 76.8(4) . . . . ?
F9 C10 C11 F11 79.2(4) . . . . ?
F9 C10 C11 F12 -163.1(4) . . . . ?
F9 C10 C11 C12 -41.6(5) . . . . ?
F14 C12 C13 F17 -172.5(4) . . . . ?
F14 C12 C13 F15 -51.5(5) . . . . ?
F14 C12 C13 F16 68.8(5) . . . . ?
N2 C4 C5 C6 -178.9(3) . . . . ?
N2 C2 C1 N1 -0.5(4) . . . . ?
F13 C12 C13 F17 69.7(5) . . . . ?
F13 C12 C13 F15 -169.3(4) . . . . ?
F13 C12 C13 F16 -49.0(5) . . . . ?
C6 C7 C8 F6 -46.2(5) . . . . ?
C6 C7 C8 F5 71.7(4) . . . . ?
C6 C7 C8 C9 -166.9(3) . . . . ?
C7 C6 C5 C4 177.9(3) . . . . ?
C4 N2 C2 C1 178.6(3) . . . . ?
C4 N2 C3 N1 -178.4(3) . . . . ?
C9 C10 C11 F11 -42.1(4) . . . . ?
C9 C10 C11 F12 75.5(4) . . . . ?
C9 C10 C11 C12 -163.0(3) . . . . ?
C2 N2 C4 C5 -94.2(4) . . . . ?
C2 N2 C3 N1 -0.1(5) . . . . ?
C3 N2 C4 C5 83.8(5) . . . . ?
C3 N2 C2 C1 0.3(4) . . . . ?
C3 N1 C1 C2 0.5(5) . . . . ?
C5 C6 C7 F3 -49.6(4) . . . . ?
C5 C6 C7 F4 67.3(4) . . . . ?
C5 C6 C7 C8 -170.6(3) . . . . ?
C1 N1 C3 N2 -0.3(5) . . . . ?
C10 C9 C8 F6 80.1(4) . . . . ?
C10 C9 C8 F5 -37.4(5) . . . . ?
C10 C9 C8 C7 -158.7(3) . . . . ?
C10 C11 C12 F14 -45.4(5) . . . . ?
C10 C11 C12 F13 74.3(4) . . . . ?
C10 C11 C12 C13 -165.4(4) . . . . ?
C11 C12 C13 F17 -51.5(5) . . . . ?
C11 C12 C13 F15 69.5(5) . . . . ?
C11 C12 C13 F16 -170.2(4) . . . . ?
C8 C9 C10 F10 -44.9(5) . . . . ?
C8 C9 C10 F9 73.8(4) . . . . ?
C8 C9 C10 C11 -165.0(3) . . . . ?

_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 2.424
_oxdiff_exptl_absorpt_empirical_full_min 0.550


