# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_les168
_database_code_depnum_ccdc_archive 'CCDC 2288120'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2023-08-11 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-butyl-2,4,5-trifluoro-N,N-dimethylbenzenaminiumtetrakis(perfluorophenyl)borate

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H16 F3 N2, C24 B F20'
_chemical_formula_sum            'C35 H16 B F23 N2'
_chemical_formula_weight         912.31

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   20.8363(9)
_cell_length_b                   11.7036(4)
_cell_length_c                   14.1501(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3450.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    19082
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.47

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9534
_exptl_absorpt_correction_T_max  0.9858

_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.1250
0 0 1 0.1250
1 2 0 0.0680
-1 -2 0 0.0680
-1 0 0 0.0400
1 0 0 0.0400

_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'

_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'

_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'

_diffrn_measurement_method       'rotation method, ω scans 1°'
_diffrn_measurement_details      
; 
2 runs, 159 frames, 1 deg., detector distance = 70 mm
;

_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67

_diffrn_reflns_number            24592
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         27.910
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8188
_reflns_number_gt                6724
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.997

_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       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area X-Red 2.3.0.0 (STOE, 2021) 
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
'absolute structure cannot be determined reliably'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+1.4933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Absolute structure cannot be determined reliably.
;
_refine_ls_abs_structure_Flack   0.4(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         8188
_refine_ls_number_parameters     556
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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_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
C1 C 0.40296(17) 0.2845(3) 0.5404(2) 0.0249(7) Uani 1 1 d . . . . .
C2 C 0.41297(18) 0.2367(3) 0.4530(3) 0.0275(8) Uani 1 1 d . . . . .
F2 F 0.47341(11) 0.22859(19) 0.42002(15) 0.0354(5) Uani 1 1 d . . . . .
C3 C 0.3614(2) 0.1975(3) 0.3987(3) 0.0346(9) Uani 1 1 d . . . . .
C4 C 0.3030(2) 0.2112(4) 0.4411(3) 0.0408(10) Uani 1 1 d . . . . .
F4 F 0.24866(14) 0.1791(3) 0.3970(2) 0.0624(8) Uani 1 1 d . . . . .
C5 C 0.2968(2) 0.2616(4) 0.5297(3) 0.0422(10) Uani 1 1 d . . . . .
F5 F 0.23873(12) 0.2756(3) 0.5674(2) 0.0658(9) Uani 1 1 d . . . . .
N6 N 0.34569(15) 0.2978(3) 0.5791(2) 0.0325(7) Uani 1 1 d . . . . .
N7 N 0.45707(15) 0.3243(2) 0.5984(2) 0.0266(6) Uani 1 1 d D . . . .
H7 H 0.4935(15) 0.306(3) 0.566(3) 0.032 Uiso 1 1 d D U . . .
C8 C 0.4567(2) 0.2663(4) 0.6939(3) 0.0351(9) Uani 1 1 d . . . . .
H8A H 0.4184 0.2897 0.7291 0.053 Uiso 1 1 calc R U . . .
H8B H 0.4952 0.2885 0.7292 0.053 Uiso 1 1 calc R U . . .
H8C H 0.4563 0.1833 0.6852 0.053 Uiso 1 1 calc R U . . .
C9 C 0.4562(2) 0.4519(3) 0.6077(3) 0.0409(10) Uani 1 1 d . . . . .
H9A H 0.4575 0.4867 0.5447 0.061 Uiso 1 1 calc R U . . .
H9B H 0.4937 0.4768 0.6441 0.061 Uiso 1 1 calc R U . . .
H9C H 0.4170 0.4757 0.6403 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3714(3) 0.1464(3) 0.3030(3) 0.0428(11) Uani 1 1 d . . . . .
H10A H 0.3320 0.1050 0.2842 0.051 Uiso 1 1 calc R U . . .
H10B H 0.4067 0.0900 0.3067 0.051 Uiso 1 1 calc R U . . .
C11 C 0.3876(2) 0.2351(3) 0.2264(3) 0.0338(9) Uani 1 1 d . . . . .
H11A H 0.3520 0.2907 0.2212 0.041 Uiso 1 1 calc R U . . .
H11B H 0.4267 0.2775 0.2450 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3984(2) 0.1792(3) 0.1312(3) 0.0325(8) Uani 1 1 d . . . . .
H12A H 0.3582 0.1418 0.1105 0.039 Uiso 1 1 calc R U . . .
H12B H 0.4317 0.1193 0.1378 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4195(2) 0.2644(4) 0.0563(3) 0.0437(10) Uani 1 1 d . . . . .
H13A H 0.3877 0.3258 0.0516 0.065 Uiso 1 1 calc R U . . .
H13B H 0.4231 0.2256 -0.0048 0.065 Uiso 1 1 calc R U . . .
H13C H 0.4612 0.2968 0.0738 0.065 Uiso 1 1 calc R U . . .
B1 B 0.6926(2) 0.2601(3) 0.5766(3) 0.0236(8) Uani 1 1 d . . . . .
C21 C 0.69190(17) 0.3737(3) 0.5049(2) 0.0236(7) Uani 1 1 d . . . . .
C22 C 0.74396(17) 0.4262(3) 0.4610(2) 0.0250(7) Uani 1 1 d . . . . .
F22 F 0.80508(10) 0.39483(18) 0.48167(15) 0.0296(5) Uani 1 1 d . . . . .
C23 C 0.73819(18) 0.5107(3) 0.3934(3) 0.0284(8) Uani 1 1 d . . . . .
F23 F 0.79097(11) 0.55601(18) 0.35303(16) 0.0354(5) Uani 1 1 d . . . . .
C24 C 0.67848(19) 0.5488(3) 0.3662(3) 0.0300(8) Uani 1 1 d . . . . .
F24 F 0.67286(12) 0.6303(2) 0.30024(17) 0.0428(6) Uani 1 1 d . . . . .
C25 C 0.62504(18) 0.5006(3) 0.4073(3) 0.0286(7) Uani 1 1 d . . . . .
F25 F 0.56596(11) 0.53534(19) 0.38174(16) 0.0365(5) Uani 1 1 d . . . . .
C26 C 0.63349(17) 0.4161(3) 0.4733(2) 0.0257(7) Uani 1 1 d . . . . .
F26 F 0.57797(10) 0.37124(18) 0.51003(15) 0.0302(5) Uani 1 1 d . . . . .
C31 C 0.76622(16) 0.2215(3) 0.6085(2) 0.0241(7) Uani 1 1 d . . . . .
C32 C 0.80458(18) 0.2982(3) 0.6583(2) 0.0266(7) Uani 1 1 d . . . . .
F32 F 0.78170(11) 0.40522(17) 0.67645(15) 0.0310(5) Uani 1 1 d . . . . .
C33 C 0.86564(18) 0.2753(3) 0.6900(3) 0.0291(8) Uani 1 1 d . . . . .
F33 F 0.90020(11) 0.3550(2) 0.73720(16) 0.0381(5) Uani 1 1 d . . . . .
C34 C 0.89294(17) 0.1701(3) 0.6724(3) 0.0298(8) Uani 1 1 d . . . . .
F34 F 0.95238(11) 0.1455(2) 0.70342(19) 0.0423(6) Uani 1 1 d . . . . .
C35 C 0.85727(19) 0.0895(3) 0.6245(3) 0.0295(8) Uani 1 1 d . . . . .
F35 F 0.88170(11) -0.01527(19) 0.60936(18) 0.0384(5) Uani 1 1 d . . . . .
C36 C 0.79517(17) 0.1151(3) 0.5969(2) 0.0256(7) Uani 1 1 d . . . . .
F36 F 0.76358(11) 0.02631(17) 0.55723(16) 0.0324(5) Uani 1 1 d . . . . .
C41 C 0.65754(17) 0.1618(3) 0.5090(2) 0.0239(7) Uani 1 1 d . . . . .
C42 C 0.68853(19) 0.1243(3) 0.4278(2) 0.0279(8) Uani 1 1 d . . . . .
F42 F 0.74686(11) 0.16744(18) 0.40488(15) 0.0334(5) Uani 1 1 d . . . . .
C43 C 0.6650(2) 0.0409(3) 0.3684(2) 0.0320(8) Uani 1 1 d . . . . .
F43 F 0.70038(13) 0.0040(2) 0.29410(15) 0.0432(6) Uani 1 1 d . . . . .
C44 C 0.6052(2) -0.0049(3) 0.3849(3) 0.0345(9) Uani 1 1 d . . . . .
F44 F 0.58118(15) -0.0853(2) 0.32695(18) 0.0499(7) Uani 1 1 d . . . . .
C45 C 0.57064(18) 0.0328(3) 0.4618(3) 0.0305(8) Uani 1 1 d . . . . .
F45 F 0.51110(11) -0.0073(2) 0.47753(18) 0.0406(6) Uani 1 1 d . . . . .
C46 C 0.59722(18) 0.1141(3) 0.5209(2) 0.0265(7) Uani 1 1 d . . . . .
F46 F 0.55844(10) 0.14727(17) 0.59352(15) 0.0293(4) Uani 1 1 d . . . . .
C51 C 0.65483(17) 0.2834(3) 0.6782(2) 0.0235(7) Uani 1 1 d . . . . .
C52 C 0.64752(17) 0.1920(3) 0.7403(2) 0.0242(7) Uani 1 1 d . . . . .
F52 F 0.66820(11) 0.08779(16) 0.71333(15) 0.0303(5) Uani 1 1 d . . . . .
C53 C 0.61919(18) 0.2000(3) 0.8286(2) 0.0260(7) Uani 1 1 d . . . . .
F53 F 0.61424(11) 0.10743(17) 0.88466(15) 0.0346(5) Uani 1 1 d . . . . .
C54 C 0.59581(17) 0.3035(3) 0.8592(2) 0.0260(7) Uani 1 1 d . . . . .
F54 F 0.56831(11) 0.3135(2) 0.94432(15) 0.0347(5) Uani 1 1 d . . . . .
C55 C 0.60205(17) 0.3972(3) 0.8011(3) 0.0258(7) Uani 1 1 d . . . . .
F55 F 0.57905(11) 0.49900(18) 0.83027(16) 0.0333(5) Uani 1 1 d . . . . .
C56 C 0.63159(17) 0.3862(3) 0.7135(2) 0.0239(7) Uani 1 1 d . . . . .
F56 F 0.63624(11) 0.48442(16) 0.66319(15) 0.0304(5) 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
C1 N6 1.322(5) . ?
C1 C2 1.374(5) . ?
C1 N7 1.470(5) . ?
C2 F2 1.346(4) . ?
C2 C3 1.399(5) . ?
C3 C4 1.365(7) . ?
C3 C10 1.495(6) . ?
C4 F4 1.347(5) . ?
C4 C5 1.391(6) . ?
C5 N6 1.305(5) . ?
C5 F5 1.333(5) . ?
N7 C9 1.499(5) . ?
N7 C8 1.513(5) . ?
N7 H7 0.91(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.539(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.521(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
B1 C51 1.661(5) . ?
B1 C31 1.662(5) . ?
B1 C41 1.664(5) . ?
B1 C21 1.673(5) . ?
C21 C26 1.388(5) . ?
C21 C22 1.393(5) . ?
C22 F22 1.357(4) . ?
C22 C23 1.381(5) . ?
C23 F23 1.348(4) . ?
C23 C24 1.377(5) . ?
C24 F24 1.339(4) . ?
C24 C25 1.377(5) . ?
C25 F25 1.346(4) . ?
C25 C26 1.371(5) . ?
C26 F26 1.373(4) . ?
C31 C32 1.393(5) . ?
C31 C36 1.393(5) . ?
C32 F32 1.364(4) . ?
C32 C33 1.375(5) . ?
C33 F33 1.354(4) . ?
C33 C34 1.379(5) . ?
C34 F34 1.345(4) . ?
C34 C35 1.378(6) . ?
C35 F35 1.345(4) . ?
C35 C36 1.385(5) . ?
C36 F36 1.352(4) . ?
C41 C46 1.386(5) . ?
C41 C42 1.390(5) . ?
C42 F42 1.356(4) . ?
C42 C43 1.378(5) . ?
C43 F43 1.355(4) . ?
C43 C44 1.377(6) . ?
C44 F44 1.344(4) . ?
C44 C45 1.378(6) . ?
C45 F45 1.345(4) . ?
C45 C46 1.382(5) . ?
C46 F46 1.364(4) . ?
C51 C56 1.390(5) . ?
C51 C52 1.393(5) . ?
C52 F52 1.349(4) . ?
C52 C53 1.385(5) . ?
C53 F53 1.346(4) . ?
C53 C54 1.375(5) . ?
C54 F54 1.340(4) . ?
C54 C55 1.377(5) . ?
C55 F55 1.349(4) . ?
C55 C56 1.390(5) . ?
C56 F56 1.355(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
N6 C1 C2 123.9(3) . . ?
N6 C1 N7 115.1(3) . . ?
C2 C1 N7 121.0(3) . . ?
F2 C2 C1 118.9(3) . . ?
F2 C2 C3 120.4(3) . . ?
C1 C2 C3 120.7(4) . . ?
C4 C3 C2 113.9(4) . . ?
C4 C3 C10 124.7(4) . . ?
C2 C3 C10 121.4(4) . . ?
F4 C4 C3 120.8(4) . . ?
F4 C4 C5 117.3(4) . . ?
C3 C4 C5 121.9(4) . . ?
N6 C5 F5 117.0(4) . . ?
N6 C5 C4 123.2(4) . . ?
F5 C5 C4 119.8(4) . . ?
C5 N6 C1 116.4(3) . . ?
C1 N7 C9 110.9(3) . . ?
C1 N7 C8 110.6(3) . . ?
C9 N7 C8 111.6(3) . . ?
C1 N7 H7 106(3) . . ?
C9 N7 H7 107(3) . . ?
C8 N7 H7 110(3) . . ?
N7 C8 H8A 109.5 . . ?
N7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N7 C9 H9A 109.5 . . ?
N7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 C11 113.6(3) . . ?
C3 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C3 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 111.6(3) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 112.3(3) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C51 B1 C31 104.3(3) . . ?
C51 B1 C41 113.8(3) . . ?
C31 B1 C41 111.9(3) . . ?
C51 B1 C21 113.0(3) . . ?
C31 B1 C21 112.8(3) . . ?
C41 B1 C21 101.4(3) . . ?
C26 C21 C22 112.4(3) . . ?
C26 C21 B1 119.1(3) . . ?
C22 C21 B1 127.9(3) . . ?
F22 C22 C23 115.1(3) . . ?
F22 C22 C21 121.0(3) . . ?
C23 C22 C21 123.8(3) . . ?
F23 C23 C24 119.4(3) . . ?
F23 C23 C22 120.3(3) . . ?
C24 C23 C22 120.3(3) . . ?
F24 C24 C23 120.3(3) . . ?
F24 C24 C25 121.0(3) . . ?
C23 C24 C25 118.7(3) . . ?
F25 C25 C26 121.2(3) . . ?
F25 C25 C24 120.1(3) . . ?
C26 C25 C24 118.6(3) . . ?
C25 C26 F26 115.2(3) . . ?
C25 C26 C21 126.1(3) . . ?
F26 C26 C21 118.7(3) . . ?
C32 C31 C36 112.8(3) . . ?
C32 C31 B1 119.5(3) . . ?
C36 C31 B1 127.6(3) . . ?
F32 C32 C33 116.2(3) . . ?
F32 C32 C31 119.1(3) . . ?
C33 C32 C31 124.7(3) . . ?
F33 C33 C32 121.2(3) . . ?
F33 C33 C34 119.0(3) . . ?
C32 C33 C34 119.8(3) . . ?
F34 C34 C35 120.7(4) . . ?
F34 C34 C33 120.8(4) . . ?
C35 C34 C33 118.5(3) . . ?
F35 C35 C34 119.9(3) . . ?
F35 C35 C36 120.4(3) . . ?
C34 C35 C36 119.6(3) . . ?
F36 C36 C35 113.9(3) . . ?
F36 C36 C31 121.7(3) . . ?
C35 C36 C31 124.4(3) . . ?
C46 C41 C42 113.2(3) . . ?
C46 C41 B1 127.4(3) . . ?
C42 C41 B1 119.3(3) . . ?
F42 C42 C43 115.9(3) . . ?
F42 C42 C41 119.8(3) . . ?
C43 C42 C41 124.2(4) . . ?
F43 C43 C44 120.0(3) . . ?
F43 C43 C42 120.3(4) . . ?
C44 C43 C42 119.7(3) . . ?
F44 C44 C43 120.4(4) . . ?
F44 C44 C45 120.8(4) . . ?
C43 C44 C45 118.8(3) . . ?
F45 C45 C44 120.0(3) . . ?
F45 C45 C46 120.6(4) . . ?
C44 C45 C46 119.3(4) . . ?
F46 C46 C45 114.5(3) . . ?
F46 C46 C41 120.9(3) . . ?
C45 C46 C41 124.6(3) . . ?
C56 C51 C52 113.6(3) . . ?
C56 C51 B1 128.2(3) . . ?
C52 C51 B1 118.2(3) . . ?
F52 C52 C53 116.9(3) . . ?
F52 C52 C51 118.7(3) . . ?
C53 C52 C51 124.4(3) . . ?
F53 C53 C54 119.8(3) . . ?
F53 C53 C52 120.7(3) . . ?
C54 C53 C52 119.6(3) . . ?
F54 C54 C53 120.8(3) . . ?
F54 C54 C55 120.5(3) . . ?
C53 C54 C55 118.8(3) . . ?
F55 C55 C54 119.2(3) . . ?
F55 C55 C56 120.8(3) . . ?
C54 C55 C56 120.0(3) . . ?
F56 C56 C55 115.0(3) . . ?
F56 C56 C51 121.3(3) . . ?
C55 C56 C51 123.7(3) . . ?

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
N6 C1 C2 F2 179.2(3) . . . . ?
N7 C1 C2 F2 -1.2(5) . . . . ?
N6 C1 C2 C3 -0.5(5) . . . . ?
N7 C1 C2 C3 179.1(3) . . . . ?
F2 C2 C3 C4 180.0(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
F2 C2 C3 C10 -0.4(5) . . . . ?
C1 C2 C3 C10 179.3(3) . . . . ?
C2 C3 C4 F4 178.9(3) . . . . ?
C10 C3 C4 F4 -0.7(6) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C10 C3 C4 C5 -178.6(4) . . . . ?
F4 C4 C5 N6 -179.0(4) . . . . ?
C3 C4 C5 N6 -1.0(7) . . . . ?
F4 C4 C5 F5 0.4(6) . . . . ?
C3 C4 C5 F5 178.5(4) . . . . ?
F5 C5 N6 C1 -179.3(4) . . . . ?
C4 C5 N6 C1 0.2(6) . . . . ?
C2 C1 N6 C5 0.6(6) . . . . ?
N7 C1 N6 C5 -179.0(3) . . . . ?
N6 C1 N7 C9 -68.2(4) . . . . ?
C2 C1 N7 C9 112.2(4) . . . . ?
N6 C1 N7 C8 56.2(4) . . . . ?
C2 C1 N7 C8 -123.4(4) . . . . ?
C4 C3 C10 C11 105.3(5) . . . . ?
C2 C3 C10 C11 -74.3(5) . . . . ?
C3 C10 C11 C12 179.0(4) . . . . ?
C10 C11 C12 C13 -175.6(4) . . . . ?
C51 B1 C21 C26 -61.5(4) . . . . ?
C31 B1 C21 C26 -179.4(3) . . . . ?
C41 B1 C21 C26 60.7(4) . . . . ?
C51 B1 C21 C22 127.5(4) . . . . ?
C31 B1 C21 C22 9.6(5) . . . . ?
C41 B1 C21 C22 -110.3(4) . . . . ?
C26 C21 C22 F22 -179.0(3) . . . . ?
B1 C21 C22 F22 -7.5(5) . . . . ?
C26 C21 C22 C23 -0.1(5) . . . . ?
B1 C21 C22 C23 171.4(3) . . . . ?
F22 C22 C23 F23 0.1(5) . . . . ?
C21 C22 C23 F23 -178.9(3) . . . . ?
F22 C22 C23 C24 179.5(3) . . . . ?
C21 C22 C23 C24 0.5(6) . . . . ?
F23 C23 C24 F24 -0.1(5) . . . . ?
C22 C23 C24 F24 -179.6(3) . . . . ?
F23 C23 C24 C25 179.2(3) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
F24 C24 C25 F25 -0.1(5) . . . . ?
C23 C24 C25 F25 -179.5(3) . . . . ?
F24 C24 C25 C26 178.8(3) . . . . ?
C23 C24 C25 C26 -0.5(5) . . . . ?
F25 C25 C26 F26 -0.1(5) . . . . ?
C24 C25 C26 F26 -179.1(3) . . . . ?
F25 C25 C26 C21 -180.0(3) . . . . ?
C24 C25 C26 C21 1.1(6) . . . . ?
C22 C21 C26 C25 -0.7(5) . . . . ?
B1 C21 C26 C25 -173.1(3) . . . . ?
C22 C21 C26 F26 179.4(3) . . . . ?
B1 C21 C26 F26 7.1(5) . . . . ?
C51 B1 C31 C32 -62.2(4) . . . . ?
C41 B1 C31 C32 174.4(3) . . . . ?
C21 B1 C31 C32 60.8(4) . . . . ?
C51 B1 C31 C36 113.3(4) . . . . ?
C41 B1 C31 C36 -10.1(5) . . . . ?
C21 B1 C31 C36 -123.8(4) . . . . ?
C36 C31 C32 F32 -178.8(3) . . . . ?
B1 C31 C32 F32 -2.7(5) . . . . ?
C36 C31 C32 C33 2.6(5) . . . . ?
B1 C31 C32 C33 178.7(3) . . . . ?
F32 C32 C33 F33 0.6(5) . . . . ?
C31 C32 C33 F33 179.3(3) . . . . ?
F32 C32 C33 C34 -178.3(3) . . . . ?
C31 C32 C33 C34 0.4(6) . . . . ?
F33 C33 C34 F34 1.6(5) . . . . ?
C32 C33 C34 F34 -179.4(3) . . . . ?
F33 C33 C34 C35 179.8(3) . . . . ?
C32 C33 C34 C35 -1.2(5) . . . . ?
F34 C34 C35 F35 0.7(5) . . . . ?
C33 C34 C35 F35 -177.5(3) . . . . ?
F34 C34 C35 C36 177.2(3) . . . . ?
C33 C34 C35 C36 -1.0(5) . . . . ?
F35 C35 C36 F36 1.4(5) . . . . ?
C34 C35 C36 F36 -175.1(3) . . . . ?
F35 C35 C36 C31 -179.1(3) . . . . ?
C34 C35 C36 C31 4.4(6) . . . . ?
C32 C31 C36 F36 174.5(3) . . . . ?
B1 C31 C36 F36 -1.2(5) . . . . ?
C32 C31 C36 C35 -5.0(5) . . . . ?
B1 C31 C36 C35 179.3(3) . . . . ?
C51 B1 C41 C46 11.6(5) . . . . ?
C31 B1 C41 C46 129.5(4) . . . . ?
C21 B1 C41 C46 -110.0(4) . . . . ?
C51 B1 C41 C42 -172.1(3) . . . . ?
C31 B1 C41 C42 -54.2(4) . . . . ?
C21 B1 C41 C42 66.3(4) . . . . ?
C46 C41 C42 F42 177.2(3) . . . . ?
B1 C41 C42 F42 0.4(5) . . . . ?
C46 C41 C42 C43 -5.3(5) . . . . ?
B1 C41 C42 C43 177.9(3) . . . . ?
F42 C42 C43 F43 2.0(5) . . . . ?
C41 C42 C43 F43 -175.5(3) . . . . ?
F42 C42 C43 C44 -178.0(3) . . . . ?
C41 C42 C43 C44 4.4(5) . . . . ?
F43 C43 C44 F44 -0.8(5) . . . . ?
C42 C43 C44 F44 179.2(3) . . . . ?
F43 C43 C44 C45 179.0(3) . . . . ?
C42 C43 C44 C45 -1.0(5) . . . . ?
F44 C44 C45 F45 -2.8(5) . . . . ?
C43 C44 C45 F45 177.5(3) . . . . ?
F44 C44 C45 C46 178.8(3) . . . . ?
C43 C44 C45 C46 -1.0(5) . . . . ?
F45 C45 C46 F46 0.2(5) . . . . ?
C44 C45 C46 F46 178.6(3) . . . . ?
F45 C45 C46 C41 -178.7(3) . . . . ?
C44 C45 C46 C41 -0.2(6) . . . . ?
C42 C41 C46 F46 -175.6(3) . . . . ?
B1 C41 C46 F46 0.9(5) . . . . ?
C42 C41 C46 C45 3.2(5) . . . . ?
B1 C41 C46 C45 179.7(3) . . . . ?
C31 B1 C51 C56 113.7(4) . . . . ?
C41 B1 C51 C56 -124.0(4) . . . . ?
C21 B1 C51 C56 -9.1(5) . . . . ?
C31 B1 C51 C52 -62.5(4) . . . . ?
C41 B1 C51 C52 59.8(4) . . . . ?
C21 B1 C51 C52 174.7(3) . . . . ?
C56 C51 C52 F52 179.8(3) . . . . ?
B1 C51 C52 F52 -3.5(5) . . . . ?
C56 C51 C52 C53 0.9(5) . . . . ?
B1 C51 C52 C53 177.6(3) . . . . ?
F52 C52 C53 F53 1.4(5) . . . . ?
C51 C52 C53 F53 -179.7(3) . . . . ?
F52 C52 C53 C54 -178.5(3) . . . . ?
C51 C52 C53 C54 0.4(6) . . . . ?
F53 C53 C54 F54 0.2(5) . . . . ?
C52 C53 C54 F54 -179.9(3) . . . . ?
F53 C53 C54 C55 179.3(3) . . . . ?
C52 C53 C54 C55 -0.8(5) . . . . ?
F54 C54 C55 F55 -1.2(5) . . . . ?
C53 C54 C55 F55 179.7(3) . . . . ?
F54 C54 C55 C56 179.0(3) . . . . ?
C53 C54 C55 C56 -0.1(5) . . . . ?
F55 C55 C56 F56 1.5(5) . . . . ?
C54 C55 C56 F56 -178.7(3) . . . . ?
F55 C55 C56 C51 -178.3(3) . . . . ?
C54 C55 C56 C51 1.5(6) . . . . ?
C52 C51 C56 F56 178.4(3) . . . . ?
B1 C51 C56 F56 2.1(6) . . . . ?
C52 C51 C56 C55 -1.8(5) . . . . ?
B1 C51 C56 C55 -178.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7 F2 0.91(2) 2.29(4) 2.782(4) 113(3) .
N7 H7 F26 0.91(2) 2.08(3) 2.865(4) 144(4) .
N7 H7 F46 0.91(2) 2.33(4) 2.960(4) 126(3) .
C8 H8A F24 0.98 2.35 3.320(5) 171.7 2_665
C8 H8C F44 0.98 2.44 2.942(5) 111.5 2_655
C9 H9C F33 0.98 2.44 3.135(5) 128.0 3_465

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046

