# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_d17132twin5
_database_code_depnum_ccdc_archive 'CCDC 1945783'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            F-F6BsubPc
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H6 B F7 N6'
_chemical_formula_sum            'C24 H6 B F7 N6'
_chemical_formula_weight         522.16

# start Validation Reply Form
_vrf_PLAT026_d17132twin5         
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         31 %     
RESPONSE: All the crystals selected for screening were incredibly
weakly diffracting and twinned. The crystal selected for data 
collection was the best available. however, this is a valuable result
for our group. 
;
_vrf_PLAT340_d17132twin5         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01295 Ang.  
RESPONSE: The above features have contributed to the precision 
of the bonds.
;
# end Validation Reply Form

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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   13.1545(4)
_cell_length_b                   19.3823(6)
_cell_length_c                   13.5266(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.621(2)
_cell_angle_gamma                90
_cell_volume                     3055.75(17)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7309
_cell_measurement_theta_min      4.56
_cell_measurement_theta_max      66.73

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.321
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5584
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'TWINABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            118237
_diffrn_reflns_av_unetI/netI     0.1312
_diffrn_reflns_av_R_equivalents  0.1421
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.688
_diffrn_reflns_theta_max         67.241
_diffrn_reflns_theta_full        67.241
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5714
_reflns_number_gt                1769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²+4.6476P] 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         5714
_refine_ls_number_parameters     533
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.1858
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2188
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.002
_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
F1A F -0.1202(6) 0.250000 0.9044(6) 0.0337(16) Uani 1 2 d S T P . .
F2A F 0.1191(5) 0.4862(3) 0.5652(5) 0.0553(16) Uani 1 1 d . . . . .
F3A F 0.2055(5) 0.5550(3) 0.7561(5) 0.0470(15) Uani 1 1 d . . . . .
F4A F 0.4759(5) 0.3193(3) 1.4464(4) 0.0579(17) Uani 1 1 d . . . . .
N1A N -0.0188(8) 0.250000 0.6865(8) 0.025(2) Uani 1 2 d S T P . .
N2A N 0.0041(6) 0.3104(3) 0.8489(5) 0.0230(14) Uani 1 1 d . . . . .
N3A N 0.1287(6) 0.3685(3) 1.0187(5) 0.0225(14) Uani 1 1 d . . . . .
N4A N 0.0830(8) 0.250000 1.0229(8) 0.0226(19) Uani 1 2 d S T P . .
C1A C -0.0053(7) 0.3067(4) 0.7433(6) 0.0264(17) Uani 1 1 d . . . . .
C2A C 0.0366(7) 0.3747(4) 0.7281(7) 0.0280(17) Uani 1 1 d . . . . .
C3A C 0.0462(7) 0.3974(5) 0.6333(7) 0.0331(19) Uani 1 1 d . . . . .
H3AA H 0.016049 0.372262 0.565321 0.040 Uiso 1 1 calc R U . . .
C4A C 0.1032(8) 0.4590(5) 0.6486(8) 0.0346(19) Uani 1 1 d . . . . .
C5A C 0.1474(9) 0.4959(4) 0.7476(9) 0.036(2) Uani 1 1 d . . . . .
C6A C 0.1413(7) 0.4719(4) 0.8411(7) 0.0297(18) Uani 1 1 d . . . . .
H6AA H 0.175629 0.495601 0.910483 0.036 Uiso 1 1 calc R U . . .
C7A C 0.0801(7) 0.4095(4) 0.8253(7) 0.0242(16) Uani 1 1 d . . . . .
C8A C 0.0689(7) 0.3675(4) 0.9092(7) 0.0242(16) Uani 1 1 d . . . . .
C9A C 0.1397(7) 0.3068(4) 1.0735(6) 0.0218(15) Uani 1 1 d . . . . .
C10A C 0.2295(7) 0.2869(4) 1.1805(7) 0.0270(18) Uani 1 1 d . . . . .
C11A C 0.3149(7) 0.3236(5) 1.2706(6) 0.0279(18) Uani 1 1 d . . . . .
H11A H 0.316837 0.372602 1.271003 0.033 Uiso 1 1 calc R U . . .
C12A C 0.3954(8) 0.2859(5) 1.3582(8) 0.041(2) Uani 1 1 d . . . . .
B1A B -0.0134(12) 0.250000 0.9094(11) 0.023(2) Uani 1 2 d S T P . .
F1C F 0.4542(5) 0.750000 0.0966(5) 0.0252(14) Uani 1 2 d S T P . .
F2C F 0.2125(5) 0.5129(3) 0.4344(5) 0.0517(16) Uani 1 1 d . . . . .
F3C F 0.1275(5) 0.4453(3) 0.2444(6) 0.0543(16) Uani 1 1 d . . . . .
F4C F -0.1434(5) 0.6818(3) -0.4455(5) 0.0604(18) Uani 1 1 d . . . . .
N1C N 0.3519(9) 0.750000 0.3120(8) 0.030(2) Uani 1 2 d S T P . .
N2C N 0.3284(5) 0.6884(3) 0.1499(5) 0.0214(13) Uani 1 1 d . . . . .
N3C N 0.2046(6) 0.6306(3) -0.0197(6) 0.0254(15) Uani 1 1 d . . . . .
N4C N 0.2525(8) 0.750000 -0.0190(8) 0.0222(19) Uani 1 2 d S T P . .
C1C C 0.3383(7) 0.6894(4) 0.2544(7) 0.0275(17) Uani 1 1 d . . . . .
C2C C 0.2983(7) 0.6264(4) 0.2761(7) 0.0267(17) Uani 1 1 d . . . . .
C3C C 0.2852(8) 0.6000(5) 0.3662(8) 0.037(2) Uani 1 1 d . . . . .
H3CA H 0.315463 0.623527 0.435579 0.045 Uiso 1 1 calc R U . . .
C4C C 0.2285(8) 0.5403(6) 0.3506(8) 0.041(2) Uani 1 1 d . . . . .
C5C C 0.1819(8) 0.5042(5) 0.2510(9) 0.041(2) Uani 1 1 d . . . . .
C6C C 0.1921(8) 0.5265(4) 0.1583(8) 0.037(2) Uani 1 1 d . . . . .
H6CA H 0.161285 0.501175 0.090442 0.044 Uiso 1 1 calc R U . . .
C7C C 0.2511(8) 0.5892(5) 0.1718(8) 0.0312(19) Uani 1 1 d . . . . .
C8C C 0.2658(7) 0.6321(4) 0.0912(7) 0.0252(17) Uani 1 1 d . . . . .
C9C C 0.1932(7) 0.6917(4) -0.0742(6) 0.0222(15) Uani 1 1 d . . . . .
C10C C 0.1019(7) 0.7137(4) -0.1820(7) 0.0258(17) Uani 1 1 d . . . . .
C11C C 0.0184(8) 0.6762(5) -0.2701(8) 0.039(2) Uani 1 1 d . . . . .
H11C H 0.016790 0.627238 -0.270020 0.047 Uiso 1 1 calc R U . . .
C12C C -0.0594(8) 0.7132(4) -0.3546(8) 0.039(2) Uani 1 1 d . . . . .
B1C B 0.3472(11) 0.750000 0.0955(10) 0.021(2) Uani 1 2 d S T P . .
F1B F 0.7886(5) 0.750000 0.0963(5) 0.0263(15) Uani 1 2 d S T P . .
F2B F 0.5451(5) 0.9868(3) 0.4339(5) 0.0539(16) Uani 1 1 d . . . . .
F3B F 0.4618(5) 1.0570(3) 0.2447(6) 0.0559(17) Uani 1 1 d . . . . .
F4B F 0.1895(5) 0.8185(3) -0.4448(5) 0.0582(17) Uani 1 1 d . . . . .
N1B N 0.6860(8) 0.750000 0.3117(8) 0.029(2) Uani 1 2 d S T P . .
N2B N 0.6625(6) 0.8127(3) 0.1511(5) 0.0245(14) Uani 1 1 d . . . . .
N3B N 0.5398(6) 0.8669(4) -0.0198(6) 0.0283(15) Uani 1 1 d . . . . .
N4B N 0.5837(7) 0.750000 -0.0199(7) 0.0179(18) Uani 1 2 d S T P . .
C1B C 0.6723(7) 0.8088(4) 0.2562(6) 0.0244(16) Uani 1 1 d . . . . .
C2B C 0.6318(8) 0.8744(4) 0.2755(8) 0.0297(18) Uani 1 1 d . . . . .
C3B C 0.6195(8) 0.8988(5) 0.3642(8) 0.036(2) Uani 1 1 d . . . . .
H3BA H 0.649223 0.874066 0.432599 0.043 Uiso 1 1 calc R U . . .
C4B C 0.5614(9) 0.9617(5) 0.3508(9) 0.040(2) Uani 1 1 d . . . . .
C5B C 0.5175(8) 0.9970(4) 0.2495(9) 0.038(2) Uani 1 1 d . . . . .
C6B C 0.5287(8) 0.9739(4) 0.1614(8) 0.035(2) Uani 1 1 d . . . . .
H6BA H 0.498064 0.999434 0.093760 0.042 Uiso 1 1 calc R U . . .
C7B C 0.5850(7) 0.9130(4) 0.1709(7) 0.0278(17) Uani 1 1 d . . . . .
C8B C 0.5995(7) 0.8659(4) 0.0941(7) 0.0236(16) Uani 1 1 d . . . . .
C9B C 0.5269(7) 0.8099(4) -0.0729(6) 0.0242(16) Uani 1 1 d . . . . .
C10B C 0.4366(7) 0.7864(4) -0.1802(7) 0.0243(17) Uani 1 1 d . . . . .
C11B C 0.3541(7) 0.8228(5) -0.2684(7) 0.0319(19) Uani 1 1 d . . . . .
H11B H 0.352891 0.871853 -0.268828 0.038 Uiso 1 1 calc R U . . .
C12B C 0.2729(8) 0.7850(5) -0.3565(8) 0.039(2) Uani 1 1 d . . . . .
B1B B 0.6812(11) 0.750000 0.0963(11) 0.022(2) Uani 1 2 d S T P . .


_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
F1A B1A 1.374(14) . ?
F2A C4A 1.346(10) . ?
F3A C5A 1.353(10) . ?
F4A C12A 1.339(10) . ?
N1A C1A 1.305(10) . ?
N1A C1A 1.305(10) 4_565 ?
N2A C1A 1.377(10) . ?
N2A C8A 1.404(10) . ?
N2A B1A 1.506(10) . ?
N3A C8A 1.317(10) . ?
N3A C9A 1.378(10) . ?
N4A C9A 1.328(10) 4_565 ?
N4A C9A 1.328(10) . ?
N4A B1A 1.470(16) . ?
C1A C2A 1.480(11) . ?
C2A C7A 1.346(12) . ?
C2A C3A 1.415(11) . ?
C3A C4A 1.374(13) . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.385(14) . ?
C5A C6A 1.383(12) . ?
C6A C7A 1.414(11) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.460(11) . ?
C9A C10A 1.433(11) . ?
C10A C11A 1.408(11) . ?
C10A C10A 1.431(15) 4_565 ?
C11A C12A 1.377(12) . ?
C11A H11A 0.9500 . ?
C12A C12A 1.391(19) 4_565 ?
F1C B1C 1.401(13) . ?
F2C C4C 1.354(10) . ?
F3C C5C 1.328(11) . ?
F4C C12C 1.358(10) . ?
N1C C1C 1.375(10) . ?
N1C C1C 1.375(10) 4_575 ?
N2C C1C 1.357(10) . ?
N2C C8C 1.376(11) . ?
N2C B1C 1.482(9) . ?
N3C C8C 1.334(10) . ?
N3C C9C 1.366(10) . ?
N4C C9C 1.380(9) 4_575 ?
N4C C9C 1.380(9) . ?
N4C B1C 1.470(15) . ?
C1C C2C 1.413(11) . ?
C2C C3C 1.404(12) . ?
C2C C7C 1.443(13) . ?
C3C C4C 1.338(14) . ?
C3C H3CA 0.9500 . ?
C4C C5C 1.384(15) . ?
C5C C6C 1.391(13) . ?
C6C C7C 1.409(12) . ?
C6C H6CA 0.9500 . ?
C7C C8C 1.452(11) . ?
C9C C10C 1.458(11) . ?
C10C C11C 1.392(12) . ?
C10C C10C 1.409(15) 4_575 ?
C11C C12C 1.335(13) . ?
C11C H11C 0.9500 . ?
C12C C12C 1.426(17) 4_575 ?
F1B B1B 1.413(14) . ?
F2B C4B 1.331(10) . ?
F3B C5B 1.360(10) . ?
F4B C12B 1.355(10) . ?
N1B C1B 1.331(10) . ?
N1B C1B 1.331(10) 4_575 ?
N2B C8B 1.323(10) . ?
N2B C1B 1.368(10) . ?
N2B B1B 1.501(10) . ?
N3B C9B 1.286(10) . ?
N3B C8B 1.367(10) . ?
N4B C9B 1.387(9) . ?
N4B C9B 1.387(9) 4_575 ?
N4B B1B 1.499(15) . ?
C1B C2B 1.449(11) . ?
C2B C3B 1.367(12) . ?
C2B C7B 1.459(13) . ?
C3B C4B 1.406(13) . ?
C3B H3BA 0.9500 . ?
C4B C5B 1.394(14) . ?
C5B C6B 1.343(13) . ?
C6B C7B 1.369(12) . ?
C6B H6BA 0.9500 . ?
C7B C8B 1.461(10) . ?
C9B C10B 1.458(11) . ?
C10B C11B 1.379(11) . ?
C10B C10B 1.411(15) 4_575 ?
C11B C12B 1.385(12) . ?
C11B H11B 0.9500 . ?
C12B C12B 1.356(18) 4_575 ?

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
C1A N1A C1A 114.7(10) . 4_565 ?
C1A N2A C8A 112.5(6) . . ?
C1A N2A B1A 124.1(7) . . ?
C8A N2A B1A 120.1(7) . . ?
C8A N3A C9A 116.8(6) . . ?
C9A N4A C9A 112.0(10) 4_565 . ?
C9A N4A B1A 123.0(5) 4_565 . ?
C9A N4A B1A 123.0(5) . . ?
N1A C1A N2A 125.2(8) . . ?
N1A C1A C2A 128.8(7) . . ?
N2A C1A C2A 103.7(7) . . ?
C7A C2A C3A 123.6(8) . . ?
C7A C2A C1A 109.1(7) . . ?
C3A C2A C1A 126.7(8) . . ?
C4A C3A C2A 113.9(9) . . ?
C4A C3A H3AA 123.1 . . ?
C2A C3A H3AA 123.1 . . ?
F2A C4A C3A 120.0(9) . . ?
F2A C4A C5A 116.7(8) . . ?
C3A C4A C5A 123.3(8) . . ?
F3A C5A C6A 118.5(9) . . ?
F3A C5A C4A 119.1(8) . . ?
C6A C5A C4A 122.3(8) . . ?
C5A C6A C7A 114.8(8) . . ?
C5A C6A H6AA 122.6 . . ?
C7A C6A H6AA 122.6 . . ?
C2A C7A C6A 122.0(8) . . ?
C2A C7A C8A 109.2(7) . . ?
C6A C7A C8A 128.0(7) . . ?
N3A C8A N2A 123.4(7) . . ?
N3A C8A C7A 130.1(7) . . ?
N2A C8A C7A 103.9(7) . . ?
N4A C9A N3A 123.2(8) . . ?
N4A C9A C10A 107.5(7) . . ?
N3A C9A C10A 127.5(7) . . ?
C11A C10A C10A 120.3(5) . 4_565 ?
C11A C10A C9A 133.7(7) . . ?
C10A C10A C9A 105.6(4) 4_565 . ?
C12A C11A C10A 117.6(8) . . ?
C12A C11A H11A 121.2 . . ?
C10A C11A H11A 121.2 . . ?
F4A C12A C11A 119.0(8) . . ?
F4A C12A C12A 118.9(5) . 4_565 ?
C11A C12A C12A 122.1(5) . 4_565 ?
F1A B1A N4A 114.8(10) . . ?
F1A B1A N2A 112.5(7) . 4_565 ?
N4A B1A N2A 107.0(7) . 4_565 ?
F1A B1A N2A 112.5(7) . . ?
N4A B1A N2A 107.0(7) . . ?
N2A B1A N2A 102.0(9) 4_565 . ?
C1C N1C C1C 117.4(10) . 4_575 ?
C1C N2C C8C 110.8(7) . . ?
C1C N2C B1C 123.3(7) . . ?
C8C N2C B1C 123.0(7) . . ?
C8C N3C C9C 116.5(7) . . ?
C9C N4C C9C 110.0(10) 4_575 . ?
C9C N4C B1C 124.1(5) 4_575 . ?
C9C N4C B1C 124.1(5) . . ?
N2C C1C N1C 121.8(8) . . ?
N2C C1C C2C 109.8(7) . . ?
N1C C1C C2C 125.7(7) . . ?
C3C C2C C1C 134.7(9) . . ?
C3C C2C C7C 119.8(8) . . ?
C1C C2C C7C 105.1(7) . . ?
C4C C3C C2C 117.5(9) . . ?
C4C C3C H3CA 121.2 . . ?
C2C C3C H3CA 121.2 . . ?
C3C C4C F2C 119.9(10) . . ?
C3C C4C C5C 123.6(9) . . ?
F2C C4C C5C 116.4(9) . . ?
F3C C5C C4C 118.8(8) . . ?
F3C C5C C6C 118.8(10) . . ?
C4C C5C C6C 122.4(10) . . ?
C5C C6C C7C 115.5(10) . . ?
C5C C6C H6CA 122.3 . . ?
C7C C6C H6CA 122.3 . . ?
C6C C7C C2C 121.2(8) . . ?
C6C C7C C8C 130.8(9) . . ?
C2C C7C C8C 107.6(7) . . ?
N3C C8C N2C 123.7(7) . . ?
N3C C8C C7C 127.6(8) . . ?
N2C C8C C7C 105.8(7) . . ?
N3C C9C N4C 121.6(8) . . ?
N3C C9C C10C 128.8(7) . . ?
N4C C9C C10C 107.4(7) . . ?
C11C C10C C10C 121.4(5) . 4_575 ?
C11C C10C C9C 131.4(7) . . ?
C10C C10C C9C 107.0(4) 4_575 . ?
C12C C11C C10C 116.1(8) . . ?
C12C C11C H11C 121.9 . . ?
C10C C11C H11C 121.9 . . ?
C11C C12C F4C 120.9(8) . . ?
C11C C12C C12C 122.5(6) . 4_575 ?
F4C C12C C12C 116.7(4) . 4_575 ?
F1C B1C N4C 111.5(9) . . ?
F1C B1C N2C 113.1(6) . . ?
N4C B1C N2C 105.6(7) . . ?
F1C B1C N2C 113.1(6) . 4_575 ?
N4C B1C N2C 105.6(7) . 4_575 ?
N2C B1C N2C 107.3(9) . 4_575 ?
C1B N1B C1B 117.9(10) . 4_575 ?
C8B N2B C1B 112.3(7) . . ?
C8B N2B B1B 123.0(8) . . ?
C1B N2B B1B 120.7(7) . . ?
C9B N3B C8B 118.3(7) . . ?
C9B N4B C9B 113.7(10) . 4_575 ?
C9B N4B B1B 122.4(5) . . ?
C9B N4B B1B 122.4(5) 4_575 . ?
N1B C1B N2B 123.8(8) . . ?
N1B C1B C2B 128.0(7) . . ?
N2B C1B C2B 105.9(7) . . ?
C3B C2B C1B 131.6(9) . . ?
C3B C2B C7B 120.4(9) . . ?
C1B C2B C7B 107.4(7) . . ?
C2B C3B C4B 117.7(9) . . ?
C2B C3B H3BA 121.2 . . ?
C4B C3B H3BA 121.2 . . ?
F2B C4B C5B 119.8(9) . . ?
F2B C4B C3B 119.9(9) . . ?
C5B C4B C3B 120.3(8) . . ?
C6B C5B F3B 121.4(10) . . ?
C6B C5B C4B 122.9(9) . . ?
F3B C5B C4B 115.7(8) . . ?
C5B C6B C7B 118.7(10) . . ?
C5B C6B H6BA 120.6 . . ?
C7B C6B H6BA 120.6 . . ?
C6B C7B C2B 120.0(8) . . ?
C6B C7B C8B 135.7(8) . . ?
C2B C7B C8B 103.6(7) . . ?
N2B C8B N3B 123.1(7) . . ?
N2B C8B C7B 109.0(7) . . ?
N3B C8B C7B 126.6(7) . . ?
N3B C9B N4B 122.1(8) . . ?
N3B C9B C10B 131.3(7) . . ?
N4B C9B C10B 104.3(7) . . ?
C11B C10B C10B 120.8(5) . 4_575 ?
C11B C10B C9B 130.7(7) . . ?
C10B C10B C9B 108.2(4) 4_575 . ?
C10B C11B C12B 117.2(8) . . ?
C10B C11B H11B 121.4 . . ?
C12B C11B H11B 121.4 . . ?
F4B C12B C12B 118.6(5) . 4_575 ?
F4B C12B C11B 119.4(8) . . ?
C12B C12B C11B 122.0(5) 4_575 . ?
F1B B1B N4B 111.6(10) . . ?
F1B B1B N2B 113.1(6) . 4_575 ?
N4B B1B N2B 105.2(7) . 4_575 ?
F1B B1B N2B 113.1(6) . . ?
N4B B1B N2B 105.2(6) . . ?
N2B B1B N2B 108.1(10) 4_575 . ?

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
C1A N1A C1A N2A -10.3(16) 4_565 . . . ?
C1A N1A C1A C2A 149.8(6) 4_565 . . . ?
C8A N2A C1A N1A 151.9(9) . . . . ?
B1A N2A C1A N1A -7.3(14) . . . . ?
C8A N2A C1A C2A -12.3(9) . . . . ?
B1A N2A C1A C2A -171.5(8) . . . . ?
N1A C1A C2A C7A -155.8(10) . . . . ?
N2A C1A C2A C7A 7.6(9) . . . . ?
N1A C1A C2A C3A 15.7(15) . . . . ?
N2A C1A C2A C3A 179.1(8) . . . . ?
C7A C2A C3A C4A -0.7(13) . . . . ?
C1A C2A C3A C4A -171.1(8) . . . . ?
C2A C3A C4A F2A 179.4(8) . . . . ?
C2A C3A C4A C5A 0.0(13) . . . . ?
F2A C4A C5A F3A -1.6(13) . . . . ?
C3A C4A C5A F3A 177.8(8) . . . . ?
F2A C4A C5A C6A -177.0(9) . . . . ?
C3A C4A C5A C6A 2.5(15) . . . . ?
F3A C5A C6A C7A -179.3(7) . . . . ?
C4A C5A C6A C7A -4.0(14) . . . . ?
C3A C2A C7A C6A -1.0(14) . . . . ?
C1A C2A C7A C6A 170.8(7) . . . . ?
C3A C2A C7A C8A -172.3(8) . . . . ?
C1A C2A C7A C8A -0.5(10) . . . . ?
C5A C6A C7A C2A 3.3(12) . . . . ?
C5A C6A C7A C8A 172.8(8) . . . . ?
C9A N3A C8A N2A 9.1(11) . . . . ?
C9A N3A C8A C7A -149.6(8) . . . . ?
C1A N2A C8A N3A -151.3(7) . . . . ?
B1A N2A C8A N3A 8.8(12) . . . . ?
C1A N2A C8A C7A 12.1(9) . . . . ?
B1A N2A C8A C7A 172.2(8) . . . . ?
C2A C7A C8A N3A 155.1(8) . . . . ?
C6A C7A C8A N3A -15.5(14) . . . . ?
C2A C7A C8A N2A -6.7(9) . . . . ?
C6A C7A C8A N2A -177.3(8) . . . . ?
C9A N4A C9A N3A 152.0(6) 4_565 . . . ?
B1A N4A C9A N3A -12.6(14) . . . . ?
C9A N4A C9A C10A -13.5(12) 4_565 . . . ?
B1A N4A C9A C10A -178.2(9) . . . . ?
C8A N3A C9A N4A -7.8(12) . . . . ?
C8A N3A C9A C10A 154.8(8) . . . . ?
N4A C9A C10A C11A -178.9(9) . . . . ?
N3A C9A C10A C11A 16.4(14) . . . . ?
N4A C9A C10A C10A 7.8(7) . . . 4_565 ?
N3A C9A C10A C10A -156.9(6) . . . 4_565 ?
C10A C10A C11A C12A -1.3(9) 4_565 . . . ?
C9A C10A C11A C12A -173.9(9) . . . . ?
C10A C11A C12A F4A -178.4(8) . . . . ?
C10A C11A C12A C12A 1.4(10) . . . 4_565 ?
C9A N4A B1A F1A 98.5(9) 4_565 . . . ?
C9A N4A B1A F1A -98.5(9) . . . . ?
C9A N4A B1A N2A -27.1(13) 4_565 . . 4_565 ?
C9A N4A B1A N2A 135.9(8) . . . 4_565 ?
C9A N4A B1A N2A -135.9(8) 4_565 . . . ?
C9A N4A B1A N2A 27.1(13) . . . . ?
C1A N2A B1A F1A -100.2(9) . . . . ?
C8A N2A B1A F1A 102.1(10) . . . . ?
C1A N2A B1A N4A 132.8(8) . . . . ?
C8A N2A B1A N4A -24.9(11) . . . . ?
C1A N2A B1A N2A 20.6(13) . . . 4_565 ?
C8A N2A B1A N2A -137.1(7) . . . 4_565 ?
C8C N2C C1C N1C -152.3(9) . . . . ?
B1C N2C C1C N1C 8.8(13) . . . . ?
C8C N2C C1C C2C 9.9(9) . . . . ?
B1C N2C C1C C2C 171.0(8) . . . . ?
C1C N1C C1C N2C 9.3(16) 4_575 . . . ?
C1C N1C C1C C2C -150.0(7) 4_575 . . . ?
N2C C1C C2C C3C -177.7(9) . . . . ?
N1C C1C C2C C3C -16.4(16) . . . . ?
N2C C1C C2C C7C -6.1(9) . . . . ?
N1C C1C C2C C7C 155.3(10) . . . . ?
C1C C2C C3C C4C 170.8(9) . . . . ?
C7C C2C C3C C4C 0.1(13) . . . . ?
C2C C3C C4C F2C -179.4(8) . . . . ?
C2C C3C C4C C5C -0.6(14) . . . . ?
C3C C4C C5C F3C 179.8(8) . . . . ?
F2C C4C C5C F3C -1.4(14) . . . . ?
C3C C4C C5C C6C 1.2(16) . . . . ?
F2C C4C C5C C6C -180.0(8) . . . . ?
F3C C5C C6C C7C -179.8(8) . . . . ?
C4C C5C C6C C7C -1.2(14) . . . . ?
C5C C6C C7C C2C 0.7(13) . . . . ?
C5C C6C C7C C8C -171.4(9) . . . . ?
C3C C2C C7C C6C -0.2(13) . . . . ?
C1C C2C C7C C6C -173.4(8) . . . . ?
C3C C2C C7C C8C 173.5(7) . . . . ?
C1C C2C C7C C8C 0.3(9) . . . . ?
C9C N3C C8C N2C -8.6(11) . . . . ?
C9C N3C C8C C7C 149.2(8) . . . . ?
C1C N2C C8C N3C 152.6(7) . . . . ?
B1C N2C C8C N3C -8.5(12) . . . . ?
C1C N2C C8C C7C -9.3(9) . . . . ?
B1C N2C C8C C7C -170.4(7) . . . . ?
C6C C7C C8C N3C 17.3(15) . . . . ?
C2C C7C C8C N3C -155.6(8) . . . . ?
C6C C7C C8C N2C 178.2(9) . . . . ?
C2C C7C C8C N2C 5.3(9) . . . . ?
C8C N3C C9C N4C 7.2(11) . . . . ?
C8C N3C C9C C10C -153.9(8) . . . . ?
C9C N4C C9C N3C -153.5(5) 4_575 . . . ?
B1C N4C C9C N3C 11.7(13) . . . . ?
C9C N4C C9C C10C 11.2(11) 4_575 . . . ?
B1C N4C C9C C10C 176.3(8) . . . . ?
N3C C9C C10C C11C -17.5(14) . . . . ?
N4C C9C C10C C11C 179.3(9) . . . . ?
N3C C9C C10C C10C 156.5(7) . . . 4_575 ?
N4C C9C C10C C10C -6.7(6) . . . 4_575 ?
C10C C10C C11C C12C 1.4(11) 4_575 . . . ?
C9C C10C C11C C12C 174.7(8) . . . . ?
C10C C11C C12C F4C 178.9(8) . . . . ?
C10C C11C C12C C12C -1.4(11) . . . 4_575 ?
C9C N4C B1C F1C -98.5(8) 4_575 . . . ?
C9C N4C B1C F1C 98.4(8) . . . . ?
C9C N4C B1C N2C 138.3(8) 4_575 . . . ?
C9C N4C B1C N2C -24.8(12) . . . . ?
C9C N4C B1C N2C 24.8(12) 4_575 . . 4_575 ?
C9C N4C B1C N2C -138.3(8) . . . 4_575 ?
C1C N2C B1C F1C 102.2(9) . . . . ?
C8C N2C B1C F1C -99.0(10) . . . . ?
C1C N2C B1C N4C -135.6(8) . . . . ?
C8C N2C B1C N4C 23.2(10) . . . . ?
C1C N2C B1C N2C -23.3(13) . . . 4_575 ?
C8C N2C B1C N2C 135.5(7) . . . 4_575 ?
C1B N1B C1B N2B -10.5(16) 4_575 . . . ?
C1B N1B C1B C2B 149.6(7) 4_575 . . . ?
C8B N2B C1B N1B 150.6(8) . . . . ?
B1B N2B C1B N1B -7.4(13) . . . . ?
C8B N2B C1B C2B -13.3(9) . . . . ?
B1B N2B C1B C2B -171.3(8) . . . . ?
N1B C1B C2B C3B 15.3(16) . . . . ?
N2B C1B C2B C3B 178.2(10) . . . . ?
N1B C1B C2B C7B -156.0(9) . . . . ?
N2B C1B C2B C7B 6.9(9) . . . . ?
C1B C2B C3B C4B -170.7(9) . . . . ?
C7B C2B C3B C4B -0.3(13) . . . . ?
C2B C3B C4B F2B 178.5(8) . . . . ?
C2B C3B C4B C5B 0.6(14) . . . . ?
F2B C4B C5B C6B -178.6(8) . . . . ?
C3B C4B C5B C6B -0.6(15) . . . . ?
F2B C4B C5B F3B 1.4(13) . . . . ?
C3B C4B C5B F3B 179.4(8) . . . . ?
F3B C5B C6B C7B -179.6(8) . . . . ?
C4B C5B C6B C7B 0.4(15) . . . . ?
C5B C6B C7B C2B -0.1(13) . . . . ?
C5B C6B C7B C8B 168.2(9) . . . . ?
C3B C2B C7B C6B 0.1(13) . . . . ?
C1B C2B C7B C6B 172.6(7) . . . . ?
C3B C2B C7B C8B -171.5(8) . . . . ?
C1B C2B C7B C8B 1.0(9) . . . . ?
C1B N2B C8B N3B -153.2(7) . . . . ?
B1B N2B C8B N3B 4.2(12) . . . . ?
C1B N2B C8B C7B 14.3(10) . . . . ?
B1B N2B C8B C7B 171.7(7) . . . . ?
C9B N3B C8B N2B 13.1(11) . . . . ?
C9B N3B C8B C7B -152.1(8) . . . . ?
C6B C7B C8B N2B -178.5(9) . . . . ?
C2B C7B C8B N2B -8.9(9) . . . . ?
C6B C7B C8B N3B -11.5(15) . . . . ?
C2B C7B C8B N3B 158.0(8) . . . . ?
C8B N3B C9B N4B -8.6(12) . . . . ?
C8B N3B C9B C10B 151.5(8) . . . . ?
C9B N4B C9B N3B 153.6(6) 4_575 . . . ?
B1B N4B C9B N3B -12.7(14) . . . . ?
C9B N4B C9B C10B -11.1(11) 4_575 . . . ?
B1B N4B C9B C10B -177.4(9) . . . . ?
N3B C9B C10B C11B 18.2(15) . . . . ?
N4B C9B C10B C11B -179.2(9) . . . . ?
N3B C9B C10B C10B -156.3(8) . . . 4_575 ?
N4B C9B C10B C10B 6.4(7) . . . 4_575 ?
C10B C10B C11B C12B -0.7(10) 4_575 . . . ?
C9B C10B C11B C12B -174.5(8) . . . . ?
C10B C11B C12B F4B 179.5(8) . . . . ?
C10B C11B C12B C12B 0.7(10) . . . 4_575 ?
C9B N4B B1B F1B -97.5(8) . . . . ?
C9B N4B B1B F1B 97.5(8) 4_575 . . . ?
C9B N4B B1B N2B 139.5(8) . . . 4_575 ?
C9B N4B B1B N2B -25.6(12) 4_575 . . 4_575 ?
C9B N4B B1B N2B 25.6(12) . . . . ?
C9B N4B B1B N2B -139.5(8) 4_575 . . . ?
C8B N2B B1B F1B 100.6(10) . . . . ?
C1B N2B B1B F1B -103.7(9) . . . . ?
C8B N2B B1B N4B -21.4(11) . . . . ?
C1B N2B B1B N4B 134.2(8) . . . . ?
C8B N2B B1B N2B -133.4(7) . . . 4_575 ?
C1B N2B B1B N2B 22.2(13) . . . 4_575 ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_d17163_a
_database_code_depnum_ccdc_archive 'CCDC 1945784'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            Cl-F12BsubPc
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 B Cl F12 N6'
_chemical_formula_sum            'C24 B Cl F12 N6'
_chemical_formula_weight         646.56

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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   11.2770(2)
_cell_length_b                   10.5657(2)
_cell_length_c                   19.0940(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.436(1)
_cell_angle_gamma                90
_cell_volume                     2264.81(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      66.36

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.729
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45198
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.938
_diffrn_reflns_theta_max         67.206
_diffrn_reflns_theta_full        67.206
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4031
_reflns_number_gt                3456
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0385P)²+1.6102P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4031
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Cl1 Cl 0.53308(4) 0.90086(4) 0.21536(2) 0.02233(12) Uani 1 1 d . . . . .
F1 F 0.85113(10) 0.43305(11) 0.13630(6) 0.0258(3) Uani 1 1 d . . . . .
F2 F 1.03975(10) 0.35309(12) 0.22643(7) 0.0351(3) Uani 1 1 d . . . . .
F3 F 1.05462(10) 0.41359(12) 0.36311(7) 0.0352(3) Uani 1 1 d . . . . .
F4 F 0.88547(10) 0.56065(11) 0.41572(6) 0.0274(3) Uani 1 1 d . . . . .
F5 F 0.52075(10) 0.63737(11) 0.52646(6) 0.0237(3) Uani 1 1 d . . . . .
F6 F 0.31415(10) 0.62902(11) 0.58740(6) 0.0263(3) Uani 1 1 d . . . . .
F7 F 0.10341(10) 0.65960(12) 0.51153(6) 0.0288(3) Uani 1 1 d . . . . .
F8 F 0.09043(9) 0.68444(10) 0.36939(6) 0.0236(3) Uani 1 1 d . . . . .
F9 F 0.05978(10) 0.56528(12) 0.12922(6) 0.0294(3) Uani 1 1 d . . . . .
F10 F 0.04182(11) 0.38495(12) 0.02654(7) 0.0353(3) Uani 1 1 d . . . . .
F11 F 0.23578(11) 0.30354(12) -0.03092(6) 0.0337(3) Uani 1 1 d . . . . .
F12 F 0.45493(10) 0.38902(10) 0.01516(6) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.61517(13) 0.65851(14) 0.24955(8) 0.0155(3) Uani 1 1 d . . . . .
N2 N 0.62062(13) 0.66162(14) 0.37435(8) 0.0172(3) Uani 1 1 d . . . . .
N3 N 0.44392(13) 0.71737(14) 0.30290(8) 0.0157(3) Uani 1 1 d . . . . .
N4 N 0.25342(13) 0.67558(14) 0.24271(8) 0.0175(3) Uani 1 1 d . . . . .
N5 N 0.42868(13) 0.66320(14) 0.18254(8) 0.0150(3) Uani 1 1 d . . . . .
N6 N 0.59040(13) 0.55096(14) 0.13987(8) 0.0168(3) Uani 1 1 d . . . . .
C1 C 0.65723(16) 0.58558(17) 0.19872(10) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.76945(16) 0.53494(17) 0.23068(10) 0.0179(4) Uani 1 1 d . . . . .
C3 C 0.85718(17) 0.46210(18) 0.20467(11) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.95226(17) 0.42182(19) 0.25031(12) 0.0251(4) Uani 1 1 d . . . . .
C5 C 0.96006(17) 0.45338(19) 0.32112(12) 0.0254(4) Uani 1 1 d . . . . .
C6 C 0.87446(17) 0.52720(18) 0.34807(10) 0.0215(4) Uani 1 1 d . . . . .
C7 C 0.77867(16) 0.56859(17) 0.30320(10) 0.0188(4) Uani 1 1 d . . . . .
C8 C 0.67251(16) 0.64009(17) 0.31498(10) 0.0174(4) Uani 1 1 d . . . . .
C9 C 0.50435(16) 0.69030(17) 0.36653(9) 0.0171(4) Uani 1 1 d . . . . .
C10 C 0.41338(16) 0.67643(17) 0.41510(10) 0.0172(4) Uani 1 1 d . . . . .
C11 C 0.41745(17) 0.65244(17) 0.48661(10) 0.0183(4) Uani 1 1 d . . . . .
C12 C 0.31238(18) 0.64638(18) 0.51776(10) 0.0204(4) Uani 1 1 d . . . . .
C13 C 0.20250(17) 0.66001(18) 0.47841(10) 0.0205(4) Uani 1 1 d . . . . .
C14 C 0.19670(16) 0.67531(17) 0.40677(10) 0.0188(4) Uani 1 1 d . . . . .
C15 C 0.30087(16) 0.68538(17) 0.37463(10) 0.0175(4) Uani 1 1 d . . . . .
C16 C 0.32374(16) 0.70116(17) 0.30183(10) 0.0168(4) Uani 1 1 d . . . . .
C17 C 0.30896(16) 0.64859(17) 0.18559(10) 0.0169(4) Uani 1 1 d . . . . .
C18 C 0.26899(17) 0.56965(17) 0.12577(10) 0.0178(4) Uani 1 1 d . . . . .
C19 C 0.15750(17) 0.52347(19) 0.10162(10) 0.0215(4) Uani 1 1 d . . . . .
C20 C 0.14793(18) 0.43372(19) 0.04934(11) 0.0242(4) Uani 1 1 d . . . . .
C21 C 0.24866(19) 0.39096(18) 0.01963(10) 0.0233(4) Uani 1 1 d . . . . .
C22 C 0.35990(17) 0.43674(17) 0.04269(10) 0.0192(4) Uani 1 1 d . . . . .
C23 C 0.37207(16) 0.52698(17) 0.09527(9) 0.0166(4) Uani 1 1 d . . . . .
C24 C 0.47485(16) 0.58359(17) 0.13582(9) 0.0157(4) Uani 1 1 d . . . . .
B1 B 0.50425(19) 0.73298(19) 0.23778(11) 0.0165(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
Cl1 B1 1.861(2) . ?
F1 C3 1.336(2) . ?
F2 C4 1.339(2) . ?
F3 C5 1.340(2) . ?
F4 C6 1.334(2) . ?
F5 C11 1.339(2) . ?
F6 C12 1.340(2) . ?
F7 C13 1.335(2) . ?
F8 C14 1.339(2) . ?
F9 C19 1.341(2) . ?
F10 C20 1.337(2) . ?
F11 C21 1.334(2) . ?
F12 C22 1.336(2) . ?
N1 C1 1.359(2) . ?
N1 C8 1.365(2) . ?
N1 B1 1.477(3) . ?
N2 C9 1.340(2) . ?
N2 C8 1.343(2) . ?
N3 C16 1.364(2) . ?
N3 C9 1.366(2) . ?
N3 B1 1.482(3) . ?
N4 C17 1.339(2) . ?
N4 C16 1.344(2) . ?
N5 C24 1.365(2) . ?
N5 C17 1.366(2) . ?
N5 B1 1.487(3) . ?
N6 C1 1.343(2) . ?
N6 C24 1.343(2) . ?
C1 C2 1.454(3) . ?
C2 C3 1.382(3) . ?
C2 C7 1.424(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.378(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.451(3) . ?
C9 C10 1.454(3) . ?
C10 C11 1.385(3) . ?
C10 C15 1.425(3) . ?
C11 C12 1.377(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.373(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.447(3) . ?
C17 C18 1.451(3) . ?
C18 C19 1.386(3) . ?
C18 C23 1.422(3) . ?
C19 C20 1.374(3) . ?
C20 C21 1.392(3) . ?
C21 C22 1.377(3) . ?
C22 C23 1.382(3) . ?
C23 C24 1.460(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 C8 113.92(15) . . ?
C1 N1 B1 122.76(15) . . ?
C8 N1 B1 122.43(16) . . ?
C9 N2 C8 116.36(15) . . ?
C16 N3 C9 113.47(15) . . ?
C16 N3 B1 122.39(15) . . ?
C9 N3 B1 122.66(16) . . ?
C17 N4 C16 116.27(15) . . ?
C24 N5 C17 113.46(15) . . ?
C24 N5 B1 122.73(15) . . ?
C17 N5 B1 121.89(16) . . ?
C1 N6 C24 116.28(16) . . ?
N6 C1 N1 123.07(16) . . ?
N6 C1 C2 130.39(17) . . ?
N1 C1 C2 104.93(15) . . ?
C3 C2 C7 119.98(17) . . ?
C3 C2 C1 132.70(18) . . ?
C7 C2 C1 107.26(16) . . ?
F1 C3 C2 120.45(17) . . ?
F1 C3 C4 120.63(17) . . ?
C2 C3 C4 118.91(18) . . ?
F2 C4 C3 120.30(19) . . ?
F2 C4 C5 118.77(18) . . ?
C3 C4 C5 120.92(18) . . ?
F3 C5 C6 120.01(19) . . ?
F3 C5 C4 118.77(18) . . ?
C6 C5 C4 121.20(18) . . ?
F4 C6 C5 120.49(17) . . ?
F4 C6 C7 120.76(18) . . ?
C5 C6 C7 118.73(18) . . ?
C6 C7 C2 120.25(18) . . ?
C6 C7 C8 132.47(18) . . ?
C2 C7 C8 107.19(16) . . ?
N2 C8 N1 122.79(16) . . ?
N2 C8 C7 130.60(17) . . ?
N1 C8 C7 104.98(16) . . ?
N2 C9 N3 123.15(17) . . ?
N2 C9 C10 130.40(17) . . ?
N3 C9 C10 105.41(15) . . ?
C11 C10 C15 119.43(17) . . ?
C11 C10 C9 133.44(17) . . ?
C15 C10 C9 107.06(16) . . ?
F5 C11 C12 119.14(17) . . ?
F5 C11 C10 121.84(17) . . ?
C12 C11 C10 119.01(17) . . ?
F6 C12 C11 120.16(17) . . ?
F6 C12 C13 118.53(17) . . ?
C11 C12 C13 121.30(18) . . ?
F7 C13 C14 120.62(17) . . ?
F7 C13 C12 119.03(17) . . ?
C14 C13 C12 120.34(18) . . ?
F8 C14 C13 119.69(17) . . ?
F8 C14 C15 120.93(17) . . ?
C13 C14 C15 119.34(17) . . ?
C14 C15 C10 120.37(17) . . ?
C14 C15 C16 132.28(17) . . ?
C10 C15 C16 107.33(16) . . ?
N4 C16 N3 122.96(16) . . ?
N4 C16 C15 129.70(17) . . ?
N3 C16 C15 105.50(15) . . ?
N4 C17 N5 123.46(16) . . ?
N4 C17 C18 128.99(17) . . ?
N5 C17 C18 105.43(16) . . ?
C19 C18 C23 120.21(17) . . ?
C19 C18 C17 131.94(18) . . ?
C23 C18 C17 107.43(16) . . ?
F9 C19 C20 120.15(17) . . ?
F9 C19 C18 120.45(17) . . ?
C20 C19 C18 119.40(18) . . ?
F10 C20 C19 120.59(18) . . ?
F10 C20 C21 118.80(18) . . ?
C19 C20 C21 120.61(18) . . ?
F11 C21 C22 120.54(18) . . ?
F11 C21 C20 118.84(17) . . ?
C22 C21 C20 120.61(18) . . ?
F12 C22 C21 118.80(17) . . ?
F12 C22 C23 121.20(17) . . ?
C21 C22 C23 119.96(18) . . ?
C22 C23 C18 119.18(17) . . ?
C22 C23 C24 133.41(18) . . ?
C18 C23 C24 106.97(15) . . ?
N6 C24 N5 123.28(16) . . ?
N6 C24 C23 130.00(17) . . ?
N5 C24 C23 105.44(15) . . ?
N1 B1 N3 105.22(15) . . ?
N1 B1 N5 105.31(15) . . ?
N3 B1 N5 105.20(15) . . ?
N1 B1 Cl1 112.27(14) . . ?
N3 B1 Cl1 113.78(13) . . ?
N5 B1 Cl1 114.22(13) . . ?

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
C24 N6 C1 N1 -5.3(3) . . . . ?
C24 N6 C1 C2 157.95(18) . . . . ?
C8 N1 C1 N6 153.43(17) . . . . ?
B1 N1 C1 N6 -16.0(3) . . . . ?
C8 N1 C1 C2 -13.5(2) . . . . ?
B1 N1 C1 C2 177.14(16) . . . . ?
N6 C1 C2 C3 19.4(3) . . . . ?
N1 C1 C2 C3 -175.02(19) . . . . ?
N6 C1 C2 C7 -157.68(18) . . . . ?
N1 C1 C2 C7 7.86(19) . . . . ?
C7 C2 C3 F1 -178.07(16) . . . . ?
C1 C2 C3 F1 5.1(3) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -176.06(19) . . . . ?
F1 C3 C4 F2 0.1(3) . . . . ?
C2 C3 C4 F2 -178.76(17) . . . . ?
F1 C3 C4 C5 178.95(17) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
F2 C4 C5 F3 -0.2(3) . . . . ?
C3 C4 C5 F3 -179.12(18) . . . . ?
F2 C4 C5 C6 177.96(18) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
F3 C5 C6 F4 0.7(3) . . . . ?
C4 C5 C6 F4 -177.49(18) . . . . ?
F3 C5 C6 C7 178.99(17) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
F4 C6 C7 C2 178.38(16) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
F4 C6 C7 C8 -5.5(3) . . . . ?
C5 C6 C7 C8 176.20(19) . . . . ?
C3 C2 C7 C6 -0.9(3) . . . . ?
C1 C2 C7 C6 176.69(16) . . . . ?
C3 C2 C7 C8 -177.88(16) . . . . ?
C1 C2 C7 C8 -0.3(2) . . . . ?
C9 N2 C8 N1 6.6(3) . . . . ?
C9 N2 C8 C7 -156.58(18) . . . . ?
C1 N1 C8 N2 -153.57(17) . . . . ?
B1 N1 C8 N2 15.9(3) . . . . ?
C1 N1 C8 C7 13.3(2) . . . . ?
B1 N1 C8 C7 -177.29(16) . . . . ?
C6 C7 C8 N2 -18.4(3) . . . . ?
C2 C7 C8 N2 158.10(18) . . . . ?
C6 C7 C8 N1 176.20(19) . . . . ?
C2 C7 C8 N1 -7.30(19) . . . . ?
C8 N2 C9 N3 -10.6(3) . . . . ?
C8 N2 C9 C10 156.00(18) . . . . ?
C16 N3 C9 N2 158.69(17) . . . . ?
B1 N3 C9 N2 -7.7(3) . . . . ?
C16 N3 C9 C10 -10.7(2) . . . . ?
B1 N3 C9 C10 -177.14(15) . . . . ?
N2 C9 C10 C11 13.6(3) . . . . ?
N3 C9 C10 C11 -178.08(19) . . . . ?
N2 C9 C10 C15 -163.17(18) . . . . ?
N3 C9 C10 C15 5.19(19) . . . . ?
C15 C10 C11 F5 176.89(16) . . . . ?
C9 C10 C11 F5 0.5(3) . . . . ?
C15 C10 C11 C12 -4.4(3) . . . . ?
C9 C10 C11 C12 179.20(19) . . . . ?
F5 C11 C12 F6 1.8(3) . . . . ?
C10 C11 C12 F6 -176.97(16) . . . . ?
F5 C11 C12 C13 -179.25(16) . . . . ?
C10 C11 C12 C13 2.0(3) . . . . ?
F6 C12 C13 F7 2.2(3) . . . . ?
C11 C12 C13 F7 -176.75(17) . . . . ?
F6 C12 C13 C14 -178.64(17) . . . . ?
C11 C12 C13 C14 2.4(3) . . . . ?
F7 C13 C14 F8 -2.9(3) . . . . ?
C12 C13 C14 F8 177.98(16) . . . . ?
F7 C13 C14 C15 174.91(17) . . . . ?
C12 C13 C14 C15 -4.2(3) . . . . ?
F8 C14 C15 C10 179.53(15) . . . . ?
C13 C14 C15 C10 1.8(3) . . . . ?
F8 C14 C15 C16 -2.6(3) . . . . ?
C13 C14 C15 C16 179.64(19) . . . . ?
C11 C10 C15 C14 2.6(3) . . . . ?
C9 C10 C15 C14 179.86(16) . . . . ?
C11 C10 C15 C16 -175.79(16) . . . . ?
C9 C10 C15 C16 1.5(2) . . . . ?
C17 N4 C16 N3 9.2(2) . . . . ?
C17 N4 C16 C15 -153.03(19) . . . . ?
C9 N3 C16 N4 -154.26(17) . . . . ?
B1 N3 C16 N4 12.2(3) . . . . ?
C9 N3 C16 C15 11.7(2) . . . . ?
B1 N3 C16 C15 178.12(15) . . . . ?
C14 C15 C16 N4 -21.1(3) . . . . ?
C10 C15 C16 N4 157.00(18) . . . . ?
C14 C15 C16 N3 174.29(19) . . . . ?
C10 C15 C16 N3 -7.62(19) . . . . ?
C16 N4 C17 N5 -9.4(3) . . . . ?
C16 N4 C17 C18 151.52(18) . . . . ?
C24 N5 C17 N4 152.87(17) . . . . ?
B1 N5 C17 N4 -11.7(3) . . . . ?
C24 N5 C17 C18 -11.9(2) . . . . ?
B1 N5 C17 C18 -176.46(16) . . . . ?
N4 C17 C18 C19 16.6(3) . . . . ?
N5 C17 C18 C19 -179.87(19) . . . . ?
N4 C17 C18 C23 -155.79(18) . . . . ?
N5 C17 C18 C23 7.79(19) . . . . ?
C23 C18 C19 F9 -178.65(16) . . . . ?
C17 C18 C19 F9 9.8(3) . . . . ?
C23 C18 C19 C20 1.7(3) . . . . ?
C17 C18 C19 C20 -169.79(19) . . . . ?
F9 C19 C20 F10 -1.6(3) . . . . ?
C18 C19 C20 F10 178.05(17) . . . . ?
F9 C19 C20 C21 179.09(18) . . . . ?
C18 C19 C20 C21 -1.3(3) . . . . ?
F10 C20 C21 F11 0.5(3) . . . . ?
C19 C20 C21 F11 179.86(18) . . . . ?
F10 C20 C21 C22 -178.57(17) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
F11 C21 C22 F12 -2.2(3) . . . . ?
C20 C21 C22 F12 176.89(17) . . . . ?
F11 C21 C22 C23 -179.77(17) . . . . ?
C20 C21 C22 C23 -0.7(3) . . . . ?
F12 C22 C23 C18 -176.41(16) . . . . ?
C21 C22 C23 C18 1.1(3) . . . . ?
F12 C22 C23 C24 -5.2(3) . . . . ?
C21 C22 C23 C24 172.36(19) . . . . ?
C19 C18 C23 C22 -1.7(3) . . . . ?
C17 C18 C23 C22 171.74(16) . . . . ?
C19 C18 C23 C24 -175.01(17) . . . . ?
C17 C18 C23 C24 -1.6(2) . . . . ?
C1 N6 C24 N5 9.6(3) . . . . ?
C1 N6 C24 C23 -155.53(18) . . . . ?
C17 N5 C24 N6 -157.36(17) . . . . ?
B1 N5 C24 N6 7.1(3) . . . . ?
C17 N5 C24 C23 10.9(2) . . . . ?
B1 N5 C24 C23 175.32(15) . . . . ?
C22 C23 C24 N6 -10.1(3) . . . . ?
C18 C23 C24 N6 161.93(18) . . . . ?
C22 C23 C24 N5 -177.19(19) . . . . ?
C18 C23 C24 N5 -5.20(19) . . . . ?
C1 N1 B1 N3 139.04(16) . . . . ?
C8 N1 B1 N3 -29.5(2) . . . . ?
C1 N1 B1 N5 28.2(2) . . . . ?
C8 N1 B1 N5 -140.33(16) . . . . ?
C1 N1 B1 Cl1 -96.69(18) . . . . ?
C8 N1 B1 Cl1 94.79(18) . . . . ?
C16 N3 B1 N1 -139.62(16) . . . . ?
C9 N3 B1 N1 25.6(2) . . . . ?
C16 N3 B1 N5 -28.7(2) . . . . ?
C9 N3 B1 N5 136.54(16) . . . . ?
C16 N3 B1 Cl1 97.08(18) . . . . ?
C9 N3 B1 Cl1 -97.71(18) . . . . ?
C24 N5 B1 N1 -23.9(2) . . . . ?
C17 N5 B1 N1 139.25(16) . . . . ?
C24 N5 B1 N3 -134.80(17) . . . . ?
C17 N5 B1 N3 28.4(2) . . . . ?
C24 N5 B1 Cl1 99.72(18) . . . . ?
C17 N5 B1 Cl1 -97.11(18) . . . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_d1641
_database_code_depnum_ccdc_archive 'CCDC 1945788'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Cl-F6BsubPc
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H6 B Cl F6 N6'
_chemical_formula_sum            'C24 H6 B Cl F6 N6'
_chemical_formula_weight         538.61

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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   13.4953(4)
_cell_length_b                   13.4233(4)
_cell_length_c                   23.0059(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4167.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9468
_cell_measurement_theta_min      3.84
_cell_measurement_theta_max      67.16

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             2144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.394
_shelx_estimated_absorpt_T_min   0.646
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6167
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            77485
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.843
_diffrn_reflns_theta_max         67.356
_diffrn_reflns_theta_full        67.356
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3708
_reflns_number_gt                3250
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0459P)²+4.1835P] 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         3708
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Cl1 Cl 0.63658(4) 0.55189(4) 0.73998(2) 0.03175(15) Uani 1 1 d . . . . .
F1 F 0.19974(10) 0.26912(9) 0.93559(6) 0.0386(3) Uani 1 1 d . . . . .
F2 F 0.17186(9) 0.45706(10) 0.96664(5) 0.0353(3) Uani 1 1 d . . . . .
F3 F 0.22083(10) 0.96550(9) 0.65535(6) 0.0391(3) Uani 1 1 d . . . . .
F4 F 0.26902(10) 0.90686(10) 0.54864(6) 0.0404(3) Uani 1 1 d . . . . .
F5 F 0.42804(11) 0.21111(11) 0.46591(5) 0.0442(4) Uani 1 1 d . . . . .
F6 F 0.40332(13) 0.07773(10) 0.54916(6) 0.0506(4) Uani 1 1 d . . . . .
N1 N 0.44463(12) 0.48864(12) 0.77095(7) 0.0224(4) Uani 1 1 d . . . . .
N2 N 0.36800(12) 0.64674(12) 0.78377(7) 0.0243(4) Uani 1 1 d . . . . .
N3 N 0.45342(12) 0.60734(12) 0.69635(7) 0.0229(4) Uani 1 1 d . . . . .
N4 N 0.46746(13) 0.55318(12) 0.59853(7) 0.0258(4) Uani 1 1 d . . . . .
N5 N 0.49693(12) 0.44086(12) 0.67675(7) 0.0227(4) Uani 1 1 d . . . . .
N6 N 0.43900(12) 0.31803(12) 0.74305(7) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.42124(14) 0.39118(14) 0.78126(8) 0.0224(4) Uani 1 1 d . . . . .
C2 C 0.35645(15) 0.39194(15) 0.83130(8) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.30771(16) 0.31426(15) 0.85969(9) 0.0267(4) Uani 1 1 d . . . . .
H3A H 0.3167 0.2467 0.8485 0.032 Uiso 1 1 calc R U . . .
C4 C 0.24635(16) 0.34033(16) 0.90442(8) 0.0280(4) Uani 1 1 d . . . . .
C5 C 0.23129(15) 0.43948(16) 0.92074(8) 0.0269(4) Uani 1 1 d . . . . .
C6 C 0.27418(15) 0.51732(16) 0.89156(8) 0.0265(4) Uani 1 1 d . . . . .
H6A H 0.2613 0.5846 0.9020 0.032 Uiso 1 1 calc R U . . .
C7 C 0.33786(15) 0.49314(15) 0.84572(8) 0.0241(4) Uani 1 1 d . . . . .
C8 C 0.38760(15) 0.55381(14) 0.80233(8) 0.0226(4) Uani 1 1 d . . . . .
C9 C 0.39573(14) 0.66895(14) 0.72932(9) 0.0232(4) Uani 1 1 d . . . . .
C10 C 0.35837(14) 0.74369(15) 0.68889(9) 0.0246(4) Uani 1 1 d . . . . .
C11 C 0.30042(15) 0.82809(15) 0.69785(10) 0.0276(4) Uani 1 1 d . . . . .
H11A H 0.2799 0.8477 0.7357 0.033 Uiso 1 1 calc R U . . .
C12 C 0.27460(15) 0.88136(15) 0.64960(10) 0.0297(5) Uani 1 1 d . . . . .
C13 C 0.30044(16) 0.85133(16) 0.59341(9) 0.0304(5) Uani 1 1 d . . . . .
C14 C 0.35588(15) 0.76712(16) 0.58344(10) 0.0288(5) Uani 1 1 d . . . . .
H14A H 0.3718 0.7458 0.5452 0.035 Uiso 1 1 calc R U . . .
C15 C 0.38753(15) 0.71473(15) 0.63230(9) 0.0256(4) Uani 1 1 d . . . . .
C16 C 0.44445(15) 0.62301(15) 0.63797(9) 0.0242(4) Uani 1 1 d . . . . .
C17 C 0.48627(15) 0.46135(15) 0.61880(9) 0.0240(4) Uani 1 1 d . . . . .
C18 C 0.47221(15) 0.36541(15) 0.59068(9) 0.0250(4) Uani 1 1 d . . . . .
C19 C 0.45995(15) 0.33970(17) 0.53255(9) 0.0285(5) Uani 1 1 d . . . . .
H19A H 0.4661 0.3876 0.5023 0.034 Uiso 1 1 calc R U . . .
C20 C 0.43863(16) 0.24222(18) 0.52111(9) 0.0320(5) Uani 1 1 d . . . . .
C21 C 0.42619(17) 0.17122(16) 0.56535(10) 0.0340(5) Uani 1 1 d . . . . .
C22 C 0.43566(16) 0.19501(16) 0.62271(9) 0.0285(5) Uani 1 1 d . . . . .
H22A H 0.4252 0.1472 0.6525 0.034 Uiso 1 1 calc R U . . .
C23 C 0.46155(14) 0.29330(15) 0.63535(9) 0.0241(4) Uani 1 1 d . . . . .
C24 C 0.47119(14) 0.34505(14) 0.69040(8) 0.0231(4) Uani 1 1 d . . . . .
B1 B 0.50636(17) 0.52069(17) 0.72086(10) 0.0237(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
Cl1 B1 1.859(2) . ?
F1 C4 1.350(2) . ?
F2 C5 1.347(2) . ?
F3 C12 1.349(2) . ?
F4 C13 1.340(2) . ?
F5 C20 1.345(2) . ?
F6 C21 1.345(3) . ?
N1 C1 1.367(3) . ?
N1 C8 1.371(3) . ?
N1 B1 1.485(3) . ?
N2 C9 1.341(3) . ?
N2 C8 1.345(3) . ?
N3 C16 1.365(3) . ?
N3 C9 1.366(3) . ?
N3 B1 1.477(3) . ?
N4 C16 1.341(3) . ?
N4 C17 1.342(3) . ?
N5 C24 1.369(3) . ?
N5 C17 1.369(3) . ?
N5 B1 1.481(3) . ?
N6 C24 1.337(3) . ?
N6 C1 1.339(3) . ?
C1 C2 1.446(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.421(3) . ?
C3 C4 1.366(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.398(3) . ?
C5 C6 1.370(3) . ?
C6 C7 1.399(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.453(3) . ?
C9 C10 1.458(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.414(3) . ?
C11 C12 1.366(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.398(3) . ?
C13 C14 1.375(3) . ?
C14 C15 1.393(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.457(3) . ?
C17 C18 1.454(3) . ?
C18 C19 1.391(3) . ?
C18 C23 1.419(3) . ?
C19 C20 1.365(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.404(3) . ?
C21 C22 1.364(3) . ?
C22 C23 1.396(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.450(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 C8 112.95(17) . . ?
C1 N1 B1 122.78(17) . . ?
C8 N1 B1 122.59(17) . . ?
C9 N2 C8 116.60(17) . . ?
C16 N3 C9 113.74(16) . . ?
C16 N3 B1 122.69(17) . . ?
C9 N3 B1 122.72(17) . . ?
C16 N4 C17 116.80(17) . . ?
C24 N5 C17 112.68(17) . . ?
C24 N5 B1 122.98(17) . . ?
C17 N5 B1 122.07(17) . . ?
C24 N6 C1 116.99(17) . . ?
N6 C1 N1 123.13(18) . . ?
N6 C1 C2 129.49(18) . . ?
N1 C1 C2 105.73(16) . . ?
C3 C2 C7 121.48(19) . . ?
C3 C2 C1 130.74(19) . . ?
C7 C2 C1 107.42(17) . . ?
C4 C3 C2 116.54(19) . . ?
C4 C3 H3A 121.7 . . ?
C2 C3 H3A 121.7 . . ?
F1 C4 C3 120.06(19) . . ?
F1 C4 C5 117.62(18) . . ?
C3 C4 C5 122.29(19) . . ?
F2 C5 C6 120.14(19) . . ?
F2 C5 C4 117.64(18) . . ?
C6 C5 C4 122.21(19) . . ?
C5 C6 C7 116.88(19) . . ?
C5 C6 H6A 121.6 . . ?
C7 C6 H6A 121.6 . . ?
C6 C7 C2 120.43(19) . . ?
C6 C7 C8 132.22(19) . . ?
C2 C7 C8 107.10(17) . . ?
N2 C8 N1 122.36(18) . . ?
N2 C8 C7 130.34(18) . . ?
N1 C8 C7 105.29(17) . . ?
N2 C9 N3 122.91(18) . . ?
N2 C9 C10 130.72(18) . . ?
N3 C9 C10 105.04(17) . . ?
C11 C10 C15 121.08(19) . . ?
C11 C10 C9 131.29(19) . . ?
C15 C10 C9 107.57(17) . . ?
C12 C11 C10 116.7(2) . . ?
C12 C11 H11A 121.7 . . ?
C10 C11 H11A 121.7 . . ?
F3 C12 C11 119.7(2) . . ?
F3 C12 C13 117.79(19) . . ?
C11 C12 C13 122.47(19) . . ?
F4 C13 C14 120.1(2) . . ?
F4 C13 C12 118.11(19) . . ?
C14 C13 C12 121.81(19) . . ?
C13 C14 C15 116.6(2) . . ?
C13 C14 H14A 121.7 . . ?
C15 C14 H14A 121.7 . . ?
C14 C15 C10 121.24(19) . . ?
C14 C15 C16 131.3(2) . . ?
C10 C15 C16 107.25(17) . . ?
N4 C16 N3 122.51(18) . . ?
N4 C16 C15 130.71(18) . . ?
N3 C16 C15 105.37(17) . . ?
N4 C17 N5 122.87(18) . . ?
N4 C17 C18 129.38(18) . . ?
N5 C17 C18 105.61(16) . . ?
C19 C18 C23 120.99(19) . . ?
C19 C18 C17 131.54(19) . . ?
C23 C18 C17 107.18(17) . . ?
C20 C19 C18 116.6(2) . . ?
C20 C19 H19A 121.7 . . ?
C18 C19 H19A 121.7 . . ?
F5 C20 C19 120.1(2) . . ?
F5 C20 C21 117.5(2) . . ?
C19 C20 C21 122.4(2) . . ?
F6 C21 C22 120.5(2) . . ?
F6 C21 C20 117.39(19) . . ?
C22 C21 C20 122.1(2) . . ?
C21 C22 C23 116.5(2) . . ?
C21 C22 H22A 121.7 . . ?
C23 C22 H22A 121.7 . . ?
C22 C23 C18 121.30(19) . . ?
C22 C23 C24 131.09(19) . . ?
C18 C23 C24 107.25(17) . . ?
N6 C24 N5 123.04(18) . . ?
N6 C24 C23 129.20(18) . . ?
N5 C24 C23 105.81(16) . . ?
N3 B1 N5 105.45(17) . . ?
N3 B1 N1 104.65(17) . . ?
N5 B1 N1 105.88(16) . . ?
N3 B1 Cl1 111.73(14) . . ?
N5 B1 Cl1 113.97(15) . . ?
N1 B1 Cl1 114.32(15) . . ?

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
C24 N6 C1 N1 -7.4(3) . . . . ?
C24 N6 C1 C2 155.8(2) . . . . ?
C8 N1 C1 N6 155.34(18) . . . . ?
B1 N1 C1 N6 -10.2(3) . . . . ?
C8 N1 C1 C2 -11.3(2) . . . . ?
B1 N1 C1 C2 -176.82(17) . . . . ?
N6 C1 C2 C3 12.3(4) . . . . ?
N1 C1 C2 C3 177.7(2) . . . . ?
N6 C1 C2 C7 -160.78(19) . . . . ?
N1 C1 C2 C7 4.7(2) . . . . ?
C7 C2 C3 C4 -4.1(3) . . . . ?
C1 C2 C3 C4 -176.3(2) . . . . ?
C2 C3 C4 F1 -177.25(18) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
F1 C4 C5 F2 0.4(3) . . . . ?
C3 C4 C5 F2 -177.86(18) . . . . ?
F1 C4 C5 C6 -179.21(18) . . . . ?
C3 C4 C5 C6 2.5(3) . . . . ?
F2 C5 C6 C7 177.70(18) . . . . ?
C4 C5 C6 C7 -2.7(3) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C5 C6 C7 C8 173.0(2) . . . . ?
C3 C2 C7 C6 4.0(3) . . . . ?
C1 C2 C7 C6 177.78(17) . . . . ?
C3 C2 C7 C8 -170.94(18) . . . . ?
C1 C2 C7 C8 2.9(2) . . . . ?
C9 N2 C8 N1 8.7(3) . . . . ?
C9 N2 C8 C7 -152.7(2) . . . . ?
C1 N1 C8 N2 -152.36(18) . . . . ?
B1 N1 C8 N2 13.2(3) . . . . ?
C1 N1 C8 C7 13.0(2) . . . . ?
B1 N1 C8 C7 178.59(17) . . . . ?
C6 C7 C8 N2 -19.6(4) . . . . ?
C2 C7 C8 N2 154.5(2) . . . . ?
C6 C7 C8 N1 176.6(2) . . . . ?
C2 C7 C8 N1 -9.3(2) . . . . ?
C8 N2 C9 N3 -9.3(3) . . . . ?
C8 N2 C9 C10 155.5(2) . . . . ?
C16 N3 C9 N2 157.52(18) . . . . ?
B1 N3 C9 N2 -12.2(3) . . . . ?
C16 N3 C9 C10 -10.6(2) . . . . ?
B1 N3 C9 C10 179.72(17) . . . . ?
N2 C9 C10 C11 17.0(4) . . . . ?
N3 C9 C10 C11 -176.2(2) . . . . ?
N2 C9 C10 C15 -160.1(2) . . . . ?
N3 C9 C10 C15 6.7(2) . . . . ?
C15 C10 C11 C12 -0.7(3) . . . . ?
C9 C10 C11 C12 -177.5(2) . . . . ?
C10 C11 C12 F3 -178.16(17) . . . . ?
C10 C11 C12 C13 2.9(3) . . . . ?
F3 C12 C13 F4 -1.1(3) . . . . ?
C11 C12 C13 F4 177.91(19) . . . . ?
F3 C12 C13 C14 179.38(18) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
F4 C13 C14 C15 178.61(18) . . . . ?
C12 C13 C14 C15 -1.8(3) . . . . ?
C13 C14 C15 C10 3.9(3) . . . . ?
C13 C14 C15 C16 178.5(2) . . . . ?
C11 C10 C15 C14 -2.7(3) . . . . ?
C9 C10 C15 C14 174.69(18) . . . . ?
C11 C10 C15 C16 -178.44(18) . . . . ?
C9 C10 C15 C16 -1.0(2) . . . . ?
C17 N4 C16 N3 9.5(3) . . . . ?
C17 N4 C16 C15 -154.9(2) . . . . ?
C9 N3 C16 N4 -157.79(18) . . . . ?
B1 N3 C16 N4 11.9(3) . . . . ?
C9 N3 C16 C15 10.0(2) . . . . ?
B1 N3 C16 C15 179.70(17) . . . . ?
C14 C15 C16 N4 -13.8(4) . . . . ?
C10 C15 C16 N4 161.3(2) . . . . ?
C14 C15 C16 N3 179.8(2) . . . . ?
C10 C15 C16 N3 -5.1(2) . . . . ?
C16 N4 C17 N5 -9.8(3) . . . . ?
C16 N4 C17 C18 151.1(2) . . . . ?
C24 N5 C17 N4 152.19(19) . . . . ?
B1 N5 C17 N4 -11.2(3) . . . . ?
C24 N5 C17 C18 -12.6(2) . . . . ?
B1 N5 C17 C18 -175.92(17) . . . . ?
N4 C17 C18 C19 18.3(4) . . . . ?
N5 C17 C18 C19 -178.3(2) . . . . ?
N4 C17 C18 C23 -155.4(2) . . . . ?
N5 C17 C18 C23 8.0(2) . . . . ?
C23 C18 C19 C20 -0.8(3) . . . . ?
C17 C18 C19 C20 -173.8(2) . . . . ?
C18 C19 C20 F5 -178.43(19) . . . . ?
C18 C19 C20 C21 2.1(3) . . . . ?
F5 C20 C21 F6 -0.9(3) . . . . ?
C19 C20 C21 F6 178.7(2) . . . . ?
F5 C20 C21 C22 179.8(2) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
F6 C21 C22 C23 178.7(2) . . . . ?
C20 C21 C22 C23 -2.0(3) . . . . ?
C21 C22 C23 C18 3.2(3) . . . . ?
C21 C22 C23 C24 175.3(2) . . . . ?
C19 C18 C23 C22 -1.9(3) . . . . ?
C17 C18 C23 C22 172.63(19) . . . . ?
C19 C18 C23 C24 -175.67(18) . . . . ?
C17 C18 C23 C24 -1.2(2) . . . . ?
C1 N6 C24 N5 7.7(3) . . . . ?
C1 N6 C24 C23 -154.1(2) . . . . ?
C17 N5 C24 N6 -153.56(19) . . . . ?
B1 N5 C24 N6 9.6(3) . . . . ?
C17 N5 C24 C23 11.9(2) . . . . ?
B1 N5 C24 C23 175.05(17) . . . . ?
C22 C23 C24 N6 -14.9(4) . . . . ?
C18 C23 C24 N6 158.1(2) . . . . ?
C22 C23 C24 N5 -179.1(2) . . . . ?
C18 C23 C24 N5 -6.1(2) . . . . ?
C16 N3 B1 N5 -28.3(2) . . . . ?
C9 N3 B1 N5 140.47(18) . . . . ?
C16 N3 B1 N1 -139.76(18) . . . . ?
C9 N3 B1 N1 29.0(2) . . . . ?
C16 N3 B1 Cl1 96.0(2) . . . . ?
C9 N3 B1 Cl1 -95.2(2) . . . . ?
C24 N5 B1 N3 -133.82(18) . . . . ?
C17 N5 B1 N3 27.8(2) . . . . ?
C24 N5 B1 N1 -23.2(2) . . . . ?
C17 N5 B1 N1 138.39(18) . . . . ?
C24 N5 B1 Cl1 103.28(19) . . . . ?
C17 N5 B1 Cl1 -95.1(2) . . . . ?
C1 N1 B1 N3 134.65(18) . . . . ?
C8 N1 B1 N3 -29.5(2) . . . . ?
C1 N1 B1 N5 23.5(2) . . . . ?
C8 N1 B1 N5 -140.67(18) . . . . ?
C1 N1 B1 Cl1 -102.80(19) . . . . ?
C8 N1 B1 Cl1 93.0(2) . . . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene, methanol'
####################################################################### 
# 
# 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_d1770a_a
_database_code_depnum_ccdc_archive 'CCDC 1945786'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;

_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;
_publcif_datablock.id            {6418a3e9-45d4-409c-b860-9e720a420d87}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Cl-F6BsubPc
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H6 B Cl F6 N6'
_chemical_formula_sum            'C24 H6 B Cl F6 N6'
_chemical_formula_weight         538.61

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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   13.4808(7)
_cell_length_b                   13.4532(8)
_cell_length_c                   23.0190(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4174.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    149(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      3.84
_cell_measurement_theta_max      66.42

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             2144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.389
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      149(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            77749
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.840
_diffrn_reflns_theta_max         66.909
_diffrn_reflns_theta_full        66.909
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3699
_reflns_number_gt                3330
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0340P)²+2.8931P] 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         3699
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
Cl1 Cl 0.63674(3) 0.55187(3) 0.74033(2) 0.02408(11) Uani 1 1 d . . . . .
F1 F 0.19975(8) 0.26989(8) 0.93544(4) 0.0331(2) Uani 1 1 d . . . . .
F2 F 0.17181(7) 0.45744(8) 0.96644(4) 0.0299(2) Uani 1 1 d . . . . .
F3 F 0.22108(7) 0.96529(7) 0.65485(5) 0.0333(3) Uani 1 1 d . . . . .
F4 F 0.26939(8) 0.90665(8) 0.54829(4) 0.0347(3) Uani 1 1 d . . . . .
F5 F 0.42725(8) 0.21159(9) 0.46605(4) 0.0380(3) Uani 1 1 d . . . . .
F6 F 0.40251(10) 0.07858(8) 0.54935(5) 0.0439(3) Uani 1 1 d . . . . .
N1 N 0.44469(9) 0.48902(10) 0.77065(5) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.36784(9) 0.64671(10) 0.78348(6) 0.0189(3) Uani 1 1 d . . . . .
N3 N 0.45322(9) 0.60727(9) 0.69608(5) 0.0183(3) Uani 1 1 d . . . . .
N4 N 0.46757(10) 0.55311(10) 0.59830(6) 0.0209(3) Uani 1 1 d . . . . .
N5 N 0.49707(10) 0.44116(10) 0.67660(5) 0.0183(3) Uani 1 1 d . . . . .
N6 N 0.43936(10) 0.31861(10) 0.74295(5) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.42141(11) 0.39161(11) 0.78110(7) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.35625(11) 0.39263(12) 0.83106(6) 0.0187(3) Uani 1 1 d . . . . .
C3 C 0.30791(12) 0.31484(12) 0.85951(7) 0.0223(3) Uani 1 1 d . . . . .
H3A H 0.3173 0.2475 0.8484 0.027 Uiso 1 1 calc R U . . .
C4 C 0.24620(12) 0.34093(13) 0.90429(7) 0.0233(3) Uani 1 1 d . . . . .
C5 C 0.23122(12) 0.43992(13) 0.92061(7) 0.0223(3) Uani 1 1 d . . . . .
C6 C 0.27407(12) 0.51769(12) 0.89129(7) 0.0211(3) Uani 1 1 d . . . . .
H6A H 0.2611 0.5848 0.9016 0.025 Uiso 1 1 calc R U . . .
C7 C 0.33774(11) 0.49348(12) 0.84553(6) 0.0190(3) Uani 1 1 d . . . . .
C8 C 0.38760(11) 0.55411(12) 0.80205(6) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.39558(11) 0.66881(11) 0.72891(7) 0.0185(3) Uani 1 1 d . . . . .
C10 C 0.35828(11) 0.74336(12) 0.68860(7) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.30027(12) 0.82773(12) 0.69769(7) 0.0233(3) Uani 1 1 d . . . . .
H11A H 0.2796 0.8472 0.7355 0.028 Uiso 1 1 calc R U . . .
C12 C 0.27462(12) 0.88118(12) 0.64916(8) 0.0250(4) Uani 1 1 d . . . . .
C13 C 0.30065(12) 0.85095(13) 0.59311(7) 0.0263(4) Uani 1 1 d . . . . .
C14 C 0.35606(12) 0.76703(13) 0.58314(7) 0.0243(4) Uani 1 1 d . . . . .
H14A H 0.3721 0.7459 0.5449 0.029 Uiso 1 1 calc R U . . .
C15 C 0.38754(12) 0.71443(12) 0.63198(7) 0.0212(3) Uani 1 1 d . . . . .
C16 C 0.44434(11) 0.62289(12) 0.63769(7) 0.0195(3) Uani 1 1 d . . . . .
C17 C 0.48647(11) 0.46144(12) 0.61861(7) 0.0192(3) Uani 1 1 d . . . . .
C18 C 0.47240(11) 0.36573(12) 0.59062(7) 0.0205(3) Uani 1 1 d . . . . .
C19 C 0.45984(12) 0.34004(13) 0.53249(7) 0.0238(4) Uani 1 1 d . . . . .
H19A H 0.4660 0.3877 0.5022 0.029 Uiso 1 1 calc R U . . .
C20 C 0.43820(13) 0.24273(14) 0.52129(7) 0.0268(4) Uani 1 1 d . . . . .
C21 C 0.42579(13) 0.17185(13) 0.56532(8) 0.0279(4) Uani 1 1 d . . . . .
C22 C 0.43586(12) 0.19564(12) 0.62280(7) 0.0241(4) Uani 1 1 d . . . . .
H22A H 0.4258 0.1479 0.6526 0.029 Uiso 1 1 calc R U . . .
C23 C 0.46168(11) 0.29395(12) 0.63535(7) 0.0197(3) Uani 1 1 d . . . . .
C24 C 0.47144(11) 0.34552(11) 0.69020(7) 0.0185(3) Uani 1 1 d . . . . .
B1 B 0.50641(13) 0.52095(13) 0.72072(8) 0.0185(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
Cl1 B1 1.8611(18) . ?
F1 C4 1.3489(19) . ?
F2 C5 1.3453(18) . ?
F3 C12 1.3486(19) . ?
F4 C13 1.3430(19) . ?
F5 C20 1.3468(19) . ?
F6 C21 1.345(2) . ?
N1 C1 1.369(2) . ?
N1 C8 1.372(2) . ?
N1 B1 1.483(2) . ?
N2 C9 1.344(2) . ?
N2 C8 1.344(2) . ?
N3 C9 1.364(2) . ?
N3 C16 1.366(2) . ?
N3 B1 1.478(2) . ?
N4 C16 1.342(2) . ?
N4 C17 1.343(2) . ?
N5 C24 1.369(2) . ?
N5 C17 1.370(2) . ?
N5 B1 1.483(2) . ?
N6 C24 1.339(2) . ?
N6 C1 1.340(2) . ?
C1 C2 1.447(2) . ?
C2 C3 1.396(2) . ?
C2 C7 1.419(2) . ?
C3 C4 1.370(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.398(2) . ?
C5 C6 1.373(2) . ?
C6 C7 1.397(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.456(2) . ?
C9 C10 1.456(2) . ?
C10 C11 1.394(2) . ?
C10 C15 1.416(2) . ?
C11 C12 1.373(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.397(3) . ?
C13 C14 1.373(3) . ?
C14 C15 1.395(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.456(2) . ?
C17 C18 1.452(2) . ?
C18 C19 1.392(2) . ?
C18 C23 1.419(2) . ?
C19 C20 1.366(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.402(3) . ?
C21 C22 1.368(2) . ?
C22 C23 1.398(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.446(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
C1 N1 C8 112.95(13) . . ?
C1 N1 B1 122.84(13) . . ?
C8 N1 B1 122.58(13) . . ?
C9 N2 C8 116.58(13) . . ?
C9 N3 C16 113.70(13) . . ?
C9 N3 B1 122.73(13) . . ?
C16 N3 B1 122.76(13) . . ?
C16 N4 C17 116.84(13) . . ?
C24 N5 C17 112.56(13) . . ?
C24 N5 B1 123.04(13) . . ?
C17 N5 B1 122.14(13) . . ?
C24 N6 C1 117.05(13) . . ?
N6 C1 N1 123.05(14) . . ?
N6 C1 C2 129.61(14) . . ?
N1 C1 C2 105.65(13) . . ?
C3 C2 C7 121.64(14) . . ?
C3 C2 C1 130.47(15) . . ?
C7 C2 C1 107.59(13) . . ?
C4 C3 C2 116.37(15) . . ?
C4 C3 H3A 121.8 . . ?
C2 C3 H3A 121.8 . . ?
F1 C4 C3 120.00(15) . . ?
F1 C4 C5 117.71(14) . . ?
C3 C4 C5 122.26(15) . . ?
F2 C5 C6 120.17(15) . . ?
F2 C5 C4 117.61(14) . . ?
C6 C5 C4 122.22(14) . . ?
C5 C6 C7 116.84(15) . . ?
C5 C6 H6A 121.6 . . ?
C7 C6 H6A 121.6 . . ?
C6 C7 C2 120.52(15) . . ?
C6 C7 C8 132.17(15) . . ?
C2 C7 C8 107.05(13) . . ?
N2 C8 N1 122.37(14) . . ?
N2 C8 C7 130.30(14) . . ?
N1 C8 C7 105.29(13) . . ?
N2 C9 N3 122.83(14) . . ?
N2 C9 C10 130.69(14) . . ?
N3 C9 C10 105.18(13) . . ?
C11 C10 C15 121.20(15) . . ?
C11 C10 C9 131.22(15) . . ?
C15 C10 C9 107.52(14) . . ?
C12 C11 C10 116.46(16) . . ?
C12 C11 H11A 121.8 . . ?
C10 C11 H11A 121.8 . . ?
F3 C12 C11 119.68(16) . . ?
F3 C12 C13 117.92(15) . . ?
C11 C12 C13 122.38(15) . . ?
F4 C13 C14 120.06(16) . . ?
F4 C13 C12 117.92(15) . . ?
C14 C13 C12 122.02(15) . . ?
C13 C14 C15 116.62(16) . . ?
C13 C14 H14A 121.7 . . ?
C15 C14 H14A 121.7 . . ?
C14 C15 C10 121.17(15) . . ?
C14 C15 C16 131.45(16) . . ?
C10 C15 C16 107.21(14) . . ?
N4 C16 N3 122.46(14) . . ?
N4 C16 C15 130.80(14) . . ?
N3 C16 C15 105.37(13) . . ?
N4 C17 N5 122.80(14) . . ?
N4 C17 C18 129.42(14) . . ?
N5 C17 C18 105.63(13) . . ?
C19 C18 C23 121.07(15) . . ?
C19 C18 C17 131.47(15) . . ?
C23 C18 C17 107.14(13) . . ?
C20 C19 C18 116.44(16) . . ?
C20 C19 H19A 121.8 . . ?
C18 C19 H19A 121.8 . . ?
F5 C20 C19 119.98(16) . . ?
F5 C20 C21 117.26(15) . . ?
C19 C20 C21 122.76(15) . . ?
F6 C21 C22 120.39(16) . . ?
F6 C21 C20 117.71(15) . . ?
C22 C21 C20 121.90(16) . . ?
C21 C22 C23 116.49(16) . . ?
C21 C22 H22A 121.8 . . ?
C23 C22 H22A 121.8 . . ?
C22 C23 C18 121.28(15) . . ?
C22 C23 C24 131.06(15) . . ?
C18 C23 C24 107.32(14) . . ?
N6 C24 N5 122.90(14) . . ?
N6 C24 C23 129.23(14) . . ?
N5 C24 C23 105.92(13) . . ?
N3 B1 N1 104.65(13) . . ?
N3 B1 N5 105.35(13) . . ?
N1 B1 N5 105.88(13) . . ?
N3 B1 Cl1 112.05(11) . . ?
N1 B1 Cl1 113.99(11) . . ?
N5 B1 Cl1 114.08(11) . . ?

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
C24 N6 C1 N1 -7.5(2) . . . . ?
C24 N6 C1 C2 155.49(16) . . . . ?
C8 N1 C1 N6 155.47(14) . . . . ?
B1 N1 C1 N6 -10.3(2) . . . . ?
C8 N1 C1 C2 -10.97(17) . . . . ?
B1 N1 C1 C2 -176.73(13) . . . . ?
N6 C1 C2 C3 12.8(3) . . . . ?
N1 C1 C2 C3 177.99(15) . . . . ?
N6 C1 C2 C7 -160.88(15) . . . . ?
N1 C1 C2 C7 4.34(16) . . . . ?
C7 C2 C3 C4 -3.7(2) . . . . ?
C1 C2 C3 C4 -176.57(15) . . . . ?
C2 C3 C4 F1 -177.42(14) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
F1 C4 C5 F2 0.3(2) . . . . ?
C3 C4 C5 F2 -177.76(14) . . . . ?
F1 C4 C5 C6 -179.15(14) . . . . ?
C3 C4 C5 C6 2.8(3) . . . . ?
F2 C5 C6 C7 177.68(14) . . . . ?
C4 C5 C6 C7 -2.9(2) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C5 C6 C7 C8 173.09(16) . . . . ?
C3 C2 C7 C6 3.6(2) . . . . ?
C1 C2 C7 C6 177.92(14) . . . . ?
C3 C2 C7 C8 -171.22(14) . . . . ?
C1 C2 C7 C8 3.11(17) . . . . ?
C9 N2 C8 N1 8.6(2) . . . . ?
C9 N2 C8 C7 -152.63(16) . . . . ?
C1 N1 C8 N2 -152.39(14) . . . . ?
B1 N1 C8 N2 13.4(2) . . . . ?
C1 N1 C8 C7 12.86(17) . . . . ?
B1 N1 C8 C7 178.66(13) . . . . ?
C6 C7 C8 N2 -19.7(3) . . . . ?
C2 C7 C8 N2 154.26(15) . . . . ?
C6 C7 C8 N1 176.68(16) . . . . ?
C2 C7 C8 N1 -9.36(16) . . . . ?
C8 N2 C9 N3 -9.2(2) . . . . ?
C8 N2 C9 C10 155.74(16) . . . . ?
C16 N3 C9 N2 157.65(14) . . . . ?
B1 N3 C9 N2 -12.3(2) . . . . ?
C16 N3 C9 C10 -10.56(17) . . . . ?
B1 N3 C9 C10 179.48(13) . . . . ?
N2 C9 C10 C11 16.9(3) . . . . ?
N3 C9 C10 C11 -176.23(16) . . . . ?
N2 C9 C10 C15 -160.27(16) . . . . ?
N3 C9 C10 C15 6.65(17) . . . . ?
C15 C10 C11 C12 -0.8(2) . . . . ?
C9 C10 C11 C12 -177.62(16) . . . . ?
C10 C11 C12 F3 -178.03(14) . . . . ?
C10 C11 C12 C13 3.0(2) . . . . ?
F3 C12 C13 F4 -1.0(2) . . . . ?
C11 C12 C13 F4 177.93(15) . . . . ?
F3 C12 C13 C14 179.18(15) . . . . ?
C11 C12 C13 C14 -1.8(3) . . . . ?
F4 C13 C14 C15 178.61(14) . . . . ?
C12 C13 C14 C15 -1.6(2) . . . . ?
C13 C14 C15 C10 3.7(2) . . . . ?
C13 C14 C15 C16 178.42(16) . . . . ?
C11 C10 C15 C14 -2.6(2) . . . . ?
C9 C10 C15 C14 174.87(14) . . . . ?
C11 C10 C15 C16 -178.43(14) . . . . ?
C9 C10 C15 C16 -0.96(17) . . . . ?
C17 N4 C16 N3 9.5(2) . . . . ?
C17 N4 C16 C15 -155.10(16) . . . . ?
C9 N3 C16 N4 -157.95(14) . . . . ?
B1 N3 C16 N4 12.0(2) . . . . ?
C9 N3 C16 C15 9.99(17) . . . . ?
B1 N3 C16 C15 179.95(13) . . . . ?
C14 C15 C16 N4 -13.8(3) . . . . ?
C10 C15 C16 N4 161.45(16) . . . . ?
C14 C15 C16 N3 179.68(16) . . . . ?
C10 C15 C16 N3 -5.09(17) . . . . ?
C16 N4 C17 N5 -9.8(2) . . . . ?
C16 N4 C17 C18 150.96(16) . . . . ?
C24 N5 C17 N4 152.27(15) . . . . ?
B1 N5 C17 N4 -11.2(2) . . . . ?
C24 N5 C17 C18 -12.44(17) . . . . ?
B1 N5 C17 C18 -175.85(13) . . . . ?
N4 C17 C18 C19 18.1(3) . . . . ?
N5 C17 C18 C19 -178.55(16) . . . . ?
N4 C17 C18 C23 -155.32(16) . . . . ?
N5 C17 C18 C23 7.99(17) . . . . ?
C23 C18 C19 C20 -0.8(2) . . . . ?
C17 C18 C19 C20 -173.52(16) . . . . ?
C18 C19 C20 F5 -178.46(15) . . . . ?
C18 C19 C20 C21 2.0(3) . . . . ?
F5 C20 C21 F6 -1.0(2) . . . . ?
C19 C20 C21 F6 178.61(16) . . . . ?
F5 C20 C21 C22 179.62(16) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
F6 C21 C22 C23 179.03(15) . . . . ?
C20 C21 C22 C23 -1.6(3) . . . . ?
C21 C22 C23 C18 2.7(2) . . . . ?
C21 C22 C23 C24 175.07(16) . . . . ?
C19 C18 C23 C22 -1.5(2) . . . . ?
C17 C18 C23 C22 172.73(14) . . . . ?
C19 C18 C23 C24 -175.54(14) . . . . ?
C17 C18 C23 C24 -1.26(17) . . . . ?
C1 N6 C24 N5 7.9(2) . . . . ?
C1 N6 C24 C23 -153.96(15) . . . . ?
C17 N5 C24 N6 -153.76(14) . . . . ?
B1 N5 C24 N6 9.5(2) . . . . ?
C17 N5 C24 C23 11.68(17) . . . . ?
B1 N5 C24 C23 174.93(13) . . . . ?
C22 C23 C24 N6 -15.0(3) . . . . ?
C18 C23 C24 N6 158.23(15) . . . . ?
C22 C23 C24 N5 -179.15(16) . . . . ?
C18 C23 C24 N5 -5.96(17) . . . . ?
C9 N3 B1 N1 29.24(19) . . . . ?
C16 N3 B1 N1 -139.82(14) . . . . ?
C9 N3 B1 N5 140.65(14) . . . . ?
C16 N3 B1 N5 -28.41(19) . . . . ?
C9 N3 B1 Cl1 -94.76(15) . . . . ?
C16 N3 B1 Cl1 96.18(15) . . . . ?
C1 N1 B1 N3 134.65(14) . . . . ?
C8 N1 B1 N3 -29.76(19) . . . . ?
C1 N1 B1 N5 23.62(19) . . . . ?
C8 N1 B1 N5 -140.79(14) . . . . ?
C1 N1 B1 Cl1 -102.60(15) . . . . ?
C8 N1 B1 Cl1 92.99(16) . . . . ?
C24 N5 B1 N3 -133.81(14) . . . . ?
C17 N5 B1 N3 27.87(19) . . . . ?
C24 N5 B1 N1 -23.28(19) . . . . ?
C17 N5 B1 N1 138.40(14) . . . . ?
C24 N5 B1 Cl1 102.88(15) . . . . ?
C17 N5 B1 Cl1 -95.44(16) . . . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.043


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_d1640
_database_code_depnum_ccdc_archive 'CCDC 1945789'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Cl-F6BsubPc
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H6 B Cl F6 N6'
_chemical_formula_sum            'C24 H6 B Cl F6 N6'
_chemical_formula_weight         538.61

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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   13.4684(5)
_cell_length_b                   13.4295(5)
_cell_length_c                   23.0284(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4165.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9838
_cell_measurement_theta_min      5.03
_cell_measurement_theta_max      67.43

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_F_000             2144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    2.395
_shelx_estimated_absorpt_T_min   0.543
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5909
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            106939
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.839
_diffrn_reflns_theta_max         67.633
_diffrn_reflns_theta_full        67.633
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3720
_reflns_number_gt                3484
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0421P)²+3.5363P] 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         3720
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cl1 Cl 0.63671(3) 0.55213(3) 0.74015(2) 0.02588(12) Uani 1 1 d . . . . .
F1 F 0.20017(8) 0.26935(8) 0.93557(5) 0.0339(3) Uani 1 1 d . . . . .
F2 F 0.17193(8) 0.45726(8) 0.96649(4) 0.0306(3) Uani 1 1 d . . . . .
F3 F 0.22097(8) 0.96593(8) 0.65494(5) 0.0348(3) Uani 1 1 d . . . . .
F4 F 0.26891(8) 0.90719(8) 0.54835(5) 0.0362(3) Uani 1 1 d . . . . .
F5 F 0.42801(9) 0.21085(9) 0.46600(4) 0.0400(3) Uani 1 1 d . . . . .
F6 F 0.40355(11) 0.07774(9) 0.54942(5) 0.0458(3) Uani 1 1 d . . . . .
N1 N 0.44479(10) 0.48891(10) 0.77064(6) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.36774(10) 0.64691(10) 0.78341(6) 0.0194(3) Uani 1 1 d . . . . .
N3 N 0.45317(10) 0.60749(10) 0.69600(6) 0.0187(3) Uani 1 1 d . . . . .
N4 N 0.46751(11) 0.55325(10) 0.59828(6) 0.0214(3) Uani 1 1 d . . . . .
N5 N 0.49722(10) 0.44106(10) 0.67651(6) 0.0186(3) Uani 1 1 d . . . . .
N6 N 0.43958(10) 0.31835(10) 0.74300(6) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.42164(12) 0.39154(12) 0.78107(7) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.35662(12) 0.39238(12) 0.83119(7) 0.0185(3) Uani 1 1 d . . . . .
C3 C 0.30806(13) 0.31448(13) 0.85958(7) 0.0223(4) Uani 1 1 d . . . . .
H3A H 0.3172 0.2470 0.8484 0.027 Uiso 1 1 calc R U . . .
C4 C 0.24668(13) 0.34062(13) 0.90436(7) 0.0242(4) Uani 1 1 d . . . . .
C5 C 0.23135(13) 0.43977(13) 0.92060(7) 0.0231(4) Uani 1 1 d . . . . .
C6 C 0.27405(12) 0.51767(13) 0.89132(7) 0.0216(3) Uani 1 1 d . . . . .
H6A H 0.2610 0.5849 0.9017 0.026 Uiso 1 1 calc R U . . .
C7 C 0.33769(12) 0.49346(12) 0.84552(7) 0.0197(3) Uani 1 1 d . . . . .
C8 C 0.38764(12) 0.55415(12) 0.80196(7) 0.0183(3) Uani 1 1 d . . . . .
C9 C 0.39555(12) 0.66908(12) 0.72894(7) 0.0187(3) Uani 1 1 d . . . . .
C10 C 0.35787(12) 0.74378(12) 0.68856(7) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.30021(12) 0.82826(12) 0.69760(8) 0.0237(4) Uani 1 1 d . . . . .
H11A H 0.2798 0.8479 0.7354 0.028 Uiso 1 1 calc R U . . .
C12 C 0.27435(13) 0.88175(13) 0.64916(8) 0.0258(4) Uani 1 1 d . . . . .
C13 C 0.30026(13) 0.85148(13) 0.59308(8) 0.0266(4) Uani 1 1 d . . . . .
C14 C 0.35546(13) 0.76723(13) 0.58313(8) 0.0251(4) Uani 1 1 d . . . . .
H14A H 0.3711 0.7458 0.5449 0.030 Uiso 1 1 calc R U . . .
C15 C 0.38738(12) 0.71473(12) 0.63197(7) 0.0214(3) Uani 1 1 d . . . . .
C16 C 0.44418(12) 0.62306(12) 0.63763(7) 0.0204(3) Uani 1 1 d . . . . .
C17 C 0.48657(12) 0.46148(12) 0.61859(7) 0.0201(3) Uani 1 1 d . . . . .
C18 C 0.47252(12) 0.36554(13) 0.59062(7) 0.0208(3) Uani 1 1 d . . . . .
C19 C 0.46010(13) 0.33966(14) 0.53245(7) 0.0247(4) Uani 1 1 d . . . . .
H19A H 0.4661 0.3874 0.5022 0.030 Uiso 1 1 calc R U . . .
C20 C 0.43876(13) 0.24199(14) 0.52124(7) 0.0277(4) Uani 1 1 d . . . . .
C21 C 0.42653(14) 0.17119(14) 0.56531(8) 0.0296(4) Uani 1 1 d . . . . .
C22 C 0.43625(13) 0.19514(13) 0.62273(8) 0.0246(4) Uani 1 1 d . . . . .
H22A H 0.4261 0.1473 0.6525 0.030 Uiso 1 1 calc R U . . .
C23 C 0.46192(12) 0.29353(12) 0.63529(7) 0.0205(3) Uani 1 1 d . . . . .
C24 C 0.47160(12) 0.34538(12) 0.69024(7) 0.0190(3) Uani 1 1 d . . . . .
B1 B 0.50671(14) 0.52107(13) 0.72062(8) 0.0187(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
Cl1 B1 1.8552(19) . ?
F1 C4 1.3509(19) . ?
F2 C5 1.3462(19) . ?
F3 C12 1.346(2) . ?
F4 C13 1.3412(19) . ?
F5 C20 1.347(2) . ?
F6 C21 1.343(2) . ?
N1 C1 1.366(2) . ?
N1 C8 1.371(2) . ?
N1 B1 1.486(2) . ?
N2 C9 1.343(2) . ?
N2 C8 1.344(2) . ?
N3 C9 1.364(2) . ?
N3 C16 1.366(2) . ?
N3 B1 1.479(2) . ?
N4 C16 1.341(2) . ?
N4 C17 1.343(2) . ?
N5 C24 1.367(2) . ?
N5 C17 1.369(2) . ?
N5 B1 1.484(2) . ?
N6 C1 1.339(2) . ?
N6 C24 1.339(2) . ?
C1 C2 1.449(2) . ?
C2 C3 1.396(2) . ?
C2 C7 1.420(2) . ?
C3 C4 1.368(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.398(3) . ?
C5 C6 1.371(2) . ?
C6 C7 1.397(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.457(2) . ?
C9 C10 1.459(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.417(2) . ?
C11 C12 1.372(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.398(3) . ?
C13 C14 1.373(3) . ?
C14 C15 1.395(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.455(2) . ?
C17 C18 1.453(2) . ?
C18 C19 1.394(2) . ?
C18 C23 1.419(2) . ?
C19 C20 1.367(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.401(3) . ?
C21 C22 1.367(3) . ?
C22 C23 1.396(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.450(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
C1 N1 C8 113.03(14) . . ?
C1 N1 B1 122.87(13) . . ?
C8 N1 B1 122.48(13) . . ?
C9 N2 C8 116.54(14) . . ?
C9 N3 C16 113.82(14) . . ?
C9 N3 B1 122.67(13) . . ?
C16 N3 B1 122.72(14) . . ?
C16 N4 C17 116.81(14) . . ?
C24 N5 C17 112.76(14) . . ?
C24 N5 B1 122.95(13) . . ?
C17 N5 B1 122.05(14) . . ?
C1 N6 C24 116.95(14) . . ?
N6 C1 N1 123.12(14) . . ?
N6 C1 C2 129.52(15) . . ?
N1 C1 C2 105.70(13) . . ?
C3 C2 C7 121.55(15) . . ?
C3 C2 C1 130.56(15) . . ?
C7 C2 C1 107.53(14) . . ?
C4 C3 C2 116.35(16) . . ?
C4 C3 H3A 121.8 . . ?
C2 C3 H3A 121.8 . . ?
F1 C4 C3 119.98(16) . . ?
F1 C4 C5 117.64(15) . . ?
C3 C4 C5 122.37(15) . . ?
F2 C5 C6 120.15(16) . . ?
F2 C5 C4 117.64(15) . . ?
C6 C5 C4 122.21(15) . . ?
C5 C6 C7 116.81(16) . . ?
C5 C6 H6A 121.6 . . ?
C7 C6 H6A 121.6 . . ?
C6 C7 C2 120.53(15) . . ?
C6 C7 C8 132.27(16) . . ?
C2 C7 C8 106.96(14) . . ?
N2 C8 N1 122.48(14) . . ?
N2 C8 C7 130.18(15) . . ?
N1 C8 C7 105.30(14) . . ?
N2 C9 N3 122.93(14) . . ?
N2 C9 C10 130.61(15) . . ?
N3 C9 C10 105.09(14) . . ?
C11 C10 C15 121.26(15) . . ?
C11 C10 C9 131.28(16) . . ?
C15 C10 C9 107.41(14) . . ?
C12 C11 C10 116.56(16) . . ?
C12 C11 H11A 121.7 . . ?
C10 C11 H11A 121.7 . . ?
F3 C12 C11 119.66(17) . . ?
F3 C12 C13 117.95(15) . . ?
C11 C12 C13 122.38(16) . . ?
F4 C13 C14 120.12(16) . . ?
F4 C13 C12 117.95(16) . . ?
C14 C13 C12 121.93(16) . . ?
C13 C14 C15 116.66(17) . . ?
C13 C14 H14A 121.7 . . ?
C15 C14 H14A 121.7 . . ?
C14 C15 C10 121.05(16) . . ?
C14 C15 C16 131.43(16) . . ?
C10 C15 C16 107.32(14) . . ?
N4 C16 N3 122.49(15) . . ?
N4 C16 C15 130.83(15) . . ?
N3 C16 C15 105.33(14) . . ?
N4 C17 N5 122.89(15) . . ?
N4 C17 C18 129.39(15) . . ?
N5 C17 C18 105.54(13) . . ?
C19 C18 C23 120.97(16) . . ?
C19 C18 C17 131.52(16) . . ?
C23 C18 C17 107.22(14) . . ?
C20 C19 C18 116.48(16) . . ?
C20 C19 H19A 121.8 . . ?
C18 C19 H19A 121.8 . . ?
F5 C20 C19 119.92(17) . . ?
F5 C20 C21 117.45(16) . . ?
C19 C20 C21 122.63(16) . . ?
F6 C21 C22 120.36(17) . . ?
F6 C21 C20 117.64(16) . . ?
C22 C21 C20 122.00(16) . . ?
C21 C22 C23 116.54(16) . . ?
C21 C22 H22A 121.7 . . ?
C23 C22 H22A 121.7 . . ?
C22 C23 C18 121.31(15) . . ?
C22 C23 C24 131.11(15) . . ?
C18 C23 C24 107.24(14) . . ?
N6 C24 N5 123.06(14) . . ?
N6 C24 C23 129.23(15) . . ?
N5 C24 C23 105.80(13) . . ?
N3 B1 N5 105.30(13) . . ?
N3 B1 N1 104.57(13) . . ?
N5 B1 N1 105.77(13) . . ?
N3 B1 Cl1 112.12(12) . . ?
N5 B1 Cl1 114.20(12) . . ?
N1 B1 Cl1 114.02(12) . . ?

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
C24 N6 C1 N1 -7.5(2) . . . . ?
C24 N6 C1 C2 155.70(16) . . . . ?
C8 N1 C1 N6 155.42(15) . . . . ?
B1 N1 C1 N6 -10.3(2) . . . . ?
C8 N1 C1 C2 -11.17(18) . . . . ?
B1 N1 C1 C2 -176.94(14) . . . . ?
N6 C1 C2 C3 12.3(3) . . . . ?
N1 C1 C2 C3 177.69(16) . . . . ?
N6 C1 C2 C7 -160.78(16) . . . . ?
N1 C1 C2 C7 4.64(17) . . . . ?
C7 C2 C3 C4 -4.3(2) . . . . ?
C1 C2 C3 C4 -176.48(16) . . . . ?
C2 C3 C4 F1 -177.27(15) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
F1 C4 C5 F2 0.5(2) . . . . ?
C3 C4 C5 F2 -177.91(15) . . . . ?
F1 C4 C5 C6 -179.14(15) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
F2 C5 C6 C7 177.69(14) . . . . ?
C4 C5 C6 C7 -2.7(2) . . . . ?
C5 C6 C7 C2 -0.5(2) . . . . ?
C5 C6 C7 C8 173.13(17) . . . . ?
C3 C2 C7 C6 4.1(2) . . . . ?
C1 C2 C7 C6 177.88(14) . . . . ?
C3 C2 C7 C8 -170.99(15) . . . . ?
C1 C2 C7 C8 2.82(17) . . . . ?
C9 N2 C8 N1 8.5(2) . . . . ?
C9 N2 C8 C7 -152.78(16) . . . . ?
C1 N1 C8 N2 -152.39(15) . . . . ?
B1 N1 C8 N2 13.4(2) . . . . ?
C1 N1 C8 C7 12.88(17) . . . . ?
B1 N1 C8 C7 178.71(14) . . . . ?
C6 C7 C8 N2 -19.7(3) . . . . ?
C2 C7 C8 N2 154.53(16) . . . . ?
C6 C7 C8 N1 176.57(17) . . . . ?
C2 C7 C8 N1 -9.17(17) . . . . ?
C8 N2 C9 N3 -9.0(2) . . . . ?
C8 N2 C9 C10 155.59(16) . . . . ?
C16 N3 C9 N2 157.48(15) . . . . ?
B1 N3 C9 N2 -12.6(2) . . . . ?
C16 N3 C9 C10 -10.47(18) . . . . ?
B1 N3 C9 C10 179.46(14) . . . . ?
N2 C9 C10 C11 17.4(3) . . . . ?
N3 C9 C10 C11 -175.95(17) . . . . ?
N2 C9 C10 C15 -160.21(16) . . . . ?
N3 C9 C10 C15 6.43(17) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?
C9 C10 C11 C12 -177.78(17) . . . . ?
C10 C11 C12 F3 -178.12(14) . . . . ?
C10 C11 C12 C13 2.8(3) . . . . ?
F3 C12 C13 F4 -1.1(2) . . . . ?
C11 C12 C13 F4 177.98(15) . . . . ?
F3 C12 C13 C14 179.29(15) . . . . ?
C11 C12 C13 C14 -1.6(3) . . . . ?
F4 C13 C14 C15 178.42(15) . . . . ?
C12 C13 C14 C15 -2.0(3) . . . . ?
C13 C14 C15 C10 4.3(2) . . . . ?
C13 C14 C15 C16 178.50(17) . . . . ?
C11 C10 C15 C14 -3.2(3) . . . . ?
C9 C10 C15 C14 174.72(15) . . . . ?
C11 C10 C15 C16 -178.63(15) . . . . ?
C9 C10 C15 C16 -0.72(18) . . . . ?
C17 N4 C16 N3 9.5(2) . . . . ?
C17 N4 C16 C15 -155.23(17) . . . . ?
C9 N3 C16 N4 -158.04(15) . . . . ?
B1 N3 C16 N4 12.0(2) . . . . ?
C9 N3 C16 C15 10.05(18) . . . . ?
B1 N3 C16 C15 -179.89(14) . . . . ?
C14 C15 C16 N4 -13.4(3) . . . . ?
C10 C15 C16 N4 161.44(17) . . . . ?
C14 C15 C16 N3 179.94(17) . . . . ?
C10 C15 C16 N3 -5.26(18) . . . . ?
C16 N4 C17 N5 -9.8(2) . . . . ?
C16 N4 C17 C18 150.91(17) . . . . ?
C24 N5 C17 N4 152.12(16) . . . . ?
B1 N5 C17 N4 -11.3(2) . . . . ?
C24 N5 C17 C18 -12.51(18) . . . . ?
B1 N5 C17 C18 -175.95(14) . . . . ?
N4 C17 C18 C19 18.3(3) . . . . ?
N5 C17 C18 C19 -178.41(17) . . . . ?
N4 C17 C18 C23 -155.31(17) . . . . ?
N5 C17 C18 C23 7.96(18) . . . . ?
C23 C18 C19 C20 -0.8(2) . . . . ?
C17 C18 C19 C20 -173.75(18) . . . . ?
C18 C19 C20 F5 -178.45(16) . . . . ?
C18 C19 C20 C21 2.0(3) . . . . ?
F5 C20 C21 F6 -1.0(3) . . . . ?
C19 C20 C21 F6 178.58(17) . . . . ?
F5 C20 C21 C22 179.75(17) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
F6 C21 C22 C23 178.94(16) . . . . ?
C20 C21 C22 C23 -1.8(3) . . . . ?
C21 C22 C23 C18 2.9(3) . . . . ?
C21 C22 C23 C24 175.25(17) . . . . ?
C19 C18 C23 C22 -1.7(3) . . . . ?
C17 C18 C23 C22 172.78(16) . . . . ?
C19 C18 C23 C24 -175.62(15) . . . . ?
C17 C18 C23 C24 -1.17(18) . . . . ?
C1 N6 C24 N5 7.9(2) . . . . ?
C1 N6 C24 C23 -154.06(16) . . . . ?
C17 N5 C24 N6 -153.75(15) . . . . ?
B1 N5 C24 N6 9.5(2) . . . . ?
C17 N5 C24 C23 11.81(18) . . . . ?
B1 N5 C24 C23 175.08(14) . . . . ?
C22 C23 C24 N6 -14.9(3) . . . . ?
C18 C23 C24 N6 158.28(16) . . . . ?
C22 C23 C24 N5 -179.21(17) . . . . ?
C18 C23 C24 N5 -6.07(18) . . . . ?
C9 N3 B1 N5 140.66(15) . . . . ?
C16 N3 B1 N5 -28.5(2) . . . . ?
C9 N3 B1 N1 29.4(2) . . . . ?
C16 N3 B1 N1 -139.76(15) . . . . ?
C9 N3 B1 Cl1 -94.59(16) . . . . ?
C16 N3 B1 Cl1 96.22(16) . . . . ?
C24 N5 B1 N3 -133.70(15) . . . . ?
C17 N5 B1 N3 28.0(2) . . . . ?
C24 N5 B1 N1 -23.3(2) . . . . ?
C17 N5 B1 N1 138.42(15) . . . . ?
C24 N5 B1 Cl1 102.87(16) . . . . ?
C17 N5 B1 Cl1 -95.38(16) . . . . ?
C1 N1 B1 N3 134.62(15) . . . . ?
C8 N1 B1 N3 -29.8(2) . . . . ?
C1 N1 B1 N5 23.7(2) . . . . ?
C8 N1 B1 N5 -140.72(14) . . . . ?
C1 N1 B1 Cl1 -102.59(16) . . . . ?
C8 N1 B1 Cl1 92.97(16) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene, heptane'
####################################################################### 
# 
# 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_d17130
_database_code_depnum_ccdc_archive 'CCDC 1945787'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            F-F12BsubPc
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 B F13 N6'
_chemical_formula_sum            'C24 B F13 N6'
_chemical_formula_weight         630.11

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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   11.5570(3)
_cell_length_b                   22.1670(6)
_cell_length_c                   26.3618(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6753.5(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      56.54

_exptl_crystal_description       Block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_F_000             3696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.726
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            148198
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.604
_diffrn_reflns_theta_max         67.250
_diffrn_reflns_theta_full        67.250
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             11988
_reflns_number_gt                10402
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.986

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0420P)²+3.4244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 4238 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11988
_refine_ls_number_parameters     1190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.2277(3) -0.06018(18) 0.95654(14) 0.0231(8) Uani 1 1 d . . . . .
C2 C 0.0626(3) -0.00648(18) 0.97249(14) 0.0220(8) Uani 1 1 d . . . . .
C3 C 0.0756(3) 0.09414(17) 0.98823(14) 0.0221(8) Uani 1 1 d . . . . .
C4 C 0.2496(3) 0.14264(17) 0.98342(14) 0.0219(8) Uani 1 1 d . . . . .
C5 C 0.4129(3) 0.09016(18) 0.96407(14) 0.0220(8) Uani 1 1 d . . . . .
C6 C 0.4014(3) -0.01182(18) 0.95284(14) 0.0242(9) Uani 1 1 d . . . . .
C7 C 0.4243(4) -0.07404(18) 0.96632(15) 0.0245(9) Uani 1 1 d . . . . .
C8 C 0.3164(3) -0.10441(18) 0.96842(15) 0.0242(9) Uani 1 1 d . . . . .
C9 C -0.0386(3) 0.01016(18) 1.00215(14) 0.0230(8) Uani 1 1 d . . . . .
C10 C -0.0289(3) 0.07278(18) 1.01229(15) 0.0249(9) Uani 1 1 d . . . . .
C11 C 0.3467(3) 0.17699(17) 1.00212(14) 0.0219(8) Uani 1 1 d . . . . .
C12 C 0.4487(3) 0.14473(17) 0.98982(14) 0.0218(8) Uani 1 1 d . . . . .
C13 C 0.5241(4) -0.10425(19) 0.98042(15) 0.0287(9) Uani 1 1 d . . . . .
C14 C 0.5176(4) -0.1633(2) 0.99529(18) 0.0350(10) Uani 1 1 d . . . . .
C15 C 0.4116(4) -0.19299(19) 0.99674(17) 0.0349(10) Uani 1 1 d . . . . .
C16 C 0.3112(4) -0.16382(18) 0.98389(16) 0.0293(9) Uani 1 1 d . . . . .
C17 C -0.1287(4) -0.02344(18) 1.02192(15) 0.0260(9) Uani 1 1 d . . . . .
C18 C -0.2089(4) 0.0052(2) 1.05167(15) 0.0291(9) Uani 1 1 d . . . . .
C19 C -0.1991(4) 0.0658(2) 1.06307(15) 0.0291(9) Uani 1 1 d . . . . .
C20 C -0.1104(4) 0.09996(19) 1.04372(16) 0.0285(9) Uani 1 1 d . . . . .
C21 C 0.3554(3) 0.22943(17) 1.03088(14) 0.0225(8) Uani 1 1 d . . . . .
C22 C 0.4625(4) 0.24923(18) 1.04568(14) 0.0238(8) Uani 1 1 d . . . . .
C23 C 0.5617(3) 0.21676(17) 1.03460(14) 0.0233(8) Uani 1 1 d . . . . .
C24 C 0.5552(3) 0.16457(17) 1.00659(14) 0.0229(8) Uani 1 1 d . . . . .
N1 N 0.2857(3) -0.00882(14) 0.94242(11) 0.0216(7) Uani 1 1 d . . . . .
N2 N 0.1146(3) -0.06065(15) 0.96805(12) 0.0240(7) Uani 1 1 d . . . . .
N3 N 0.1164(3) 0.04646(14) 0.96054(12) 0.0213(7) Uani 1 1 d . . . . .
N4 N 0.1383(3) 0.14406(14) 0.99738(12) 0.0228(7) Uani 1 1 d . . . . .
N5 N 0.2964(3) 0.09635(14) 0.95553(11) 0.0208(7) Uani 1 1 d . . . . .
N6 N 0.4682(3) 0.03723(14) 0.95992(12) 0.0222(7) Uani 1 1 d . . . . .
B1 B 0.2259(4) 0.0490(2) 0.93074(16) 0.0214(9) Uani 1 1 d . . . . .
F1 F 0.2097(2) 0.05876(10) 0.87912(8) 0.0275(5) Uani 1 1 d . . . . .
F2 F 0.6279(2) -0.07680(11) 0.97850(10) 0.0371(6) Uani 1 1 d . . . . .
F3 F 0.6134(3) -0.19365(13) 1.00737(12) 0.0536(8) Uani 1 1 d . . . . .
F4 F 0.4098(3) -0.25148(12) 1.00969(12) 0.0516(8) Uani 1 1 d . . . . .
F5 F 0.2102(2) -0.19335(11) 0.98578(10) 0.0400(6) Uani 1 1 d . . . . .
F6 F -0.1384(2) -0.08272(11) 1.01182(9) 0.0328(5) Uani 1 1 d . . . . .
F7 F -0.2989(2) -0.02551(12) 1.07133(9) 0.0387(6) Uani 1 1 d . . . . .
F8 F -0.2796(2) 0.09137(12) 1.09292(9) 0.0393(6) Uani 1 1 d . . . . .
F9 F -0.1043(2) 0.15916(11) 1.05473(10) 0.0375(6) Uani 1 1 d . . . . .
F10 F 0.26068(19) 0.26047(10) 1.04468(9) 0.0299(5) Uani 1 1 d . . . . .
F11 F 0.4719(2) 0.30079(10) 1.07236(8) 0.0296(5) Uani 1 1 d . . . . .
F12 F 0.66358(19) 0.23582(10) 1.05283(8) 0.0289(5) Uani 1 1 d . . . . .
F13 F 0.65185(19) 0.13346(10) 0.99597(9) 0.0281(5) Uani 1 1 d . . . . .
C25 C 0.4018(3) -0.05338(18) 0.64182(14) 0.0235(8) Uani 1 1 d . . . . .
C26 C 0.4068(3) 0.04189(18) 0.60924(14) 0.0232(8) Uani 1 1 d . . . . .
C27 C 0.2401(4) 0.09726(19) 0.60285(15) 0.0267(9) Uani 1 1 d . . . . .
C28 C 0.0684(4) 0.05623(19) 0.62845(14) 0.0269(9) Uani 1 1 d . . . . .
C29 C 0.0624(4) -0.03971(18) 0.65955(14) 0.0250(9) Uani 1 1 d . . . . .
C30 C 0.2303(3) -0.09347(17) 0.66770(14) 0.0219(8) Uani 1 1 d . . . . .
C31 C 0.3213(3) -0.12566(18) 0.69434(15) 0.0247(9) Uani 1 1 d . . . . .
C32 C 0.4282(4) -0.10019(18) 0.67830(14) 0.0247(8) Uani 1 1 d . . . . .
C33 C 0.4394(4) 0.10562(18) 0.60810(14) 0.0254(9) Uani 1 1 d . . . . .
C34 C 0.3349(4) 0.13972(18) 0.60440(15) 0.0274(9) Uani 1 1 d . . . . .
C35 C -0.0360(4) 0.0512(2) 0.65892(15) 0.0291(9) Uani 1 1 d . . . . .
C36 C -0.0412(3) -0.0091(2) 0.67708(14) 0.0269(9) Uani 1 1 d . . . . .
C37 C 0.3219(4) -0.16983(19) 0.73166(15) 0.0283(9) Uani 1 1 d . . . . .
C38 C 0.4247(4) -0.1890(2) 0.75164(16) 0.0338(10) Uani 1 1 d . . . . .
C39 C 0.5287(4) -0.1631(2) 0.73655(16) 0.0332(10) Uani 1 1 d . . . . .
C40 C 0.5313(4) -0.11929(19) 0.69971(16) 0.0282(9) Uani 1 1 d . . . . .
C41 C 0.5443(4) 0.13503(19) 0.61294(16) 0.0294(9) Uani 1 1 d . . . . .
C42 C 0.5469(4) 0.1967(2) 0.61257(17) 0.0344(10) Uani 1 1 d . . . . .
C43 C 0.4452(5) 0.22979(19) 0.60997(17) 0.0370(11) Uani 1 1 d . . . . .
C44 C 0.3403(4) 0.20182(19) 0.60626(16) 0.0340(10) Uani 1 1 d . . . . .
C45 C -0.1186(4) 0.0927(2) 0.67410(16) 0.0330(10) Uani 1 1 d . . . . .
C46 C -0.2066(4) 0.0740(2) 0.70522(17) 0.0384(11) Uani 1 1 d . . . . .
C47 C -0.2140(4) 0.0146(2) 0.72185(16) 0.0357(11) Uani 1 1 d . . . . .
C48 C -0.1316(4) -0.0270(2) 0.70834(16) 0.0308(10) Uani 1 1 d . . . . .
N7 N 0.2850(3) -0.05752(14) 0.63335(12) 0.0220(7) Uani 1 1 d . . . . .
N8 N 0.4653(3) -0.00543(15) 0.62723(12) 0.0240(7) Uani 1 1 d . . . . .
N9 N 0.2904(3) 0.04132(14) 0.59960(11) 0.0224(7) Uani 1 1 d . . . . .
N10 N 0.1281(3) 0.10511(15) 0.61406(13) 0.0289(8) Uani 1 1 d . . . . .
N11 N 0.1128(3) -0.00102(15) 0.62613(12) 0.0235(7) Uani 1 1 d . . . . .
N12 N 0.1170(3) -0.08769(16) 0.67902(12) 0.0258(7) Uani 1 1 d . . . . .
B2 B 0.2224(4) -0.0154(2) 0.59914(15) 0.0217(9) Uani 1 1 d . . . . .
F14 F 0.2057(2) -0.03868(11) 0.55053(8) 0.0294(5) Uani 1 1 d . . . . .
F15 F 0.2231(2) -0.19487(11) 0.74827(9) 0.0358(6) Uani 1 1 d . . . . .
F16 F 0.4269(3) -0.23281(13) 0.78643(10) 0.0485(7) Uani 1 1 d . . . . .
F17 F 0.6268(2) -0.18257(14) 0.75821(10) 0.0495(7) Uani 1 1 d . . . . .
F18 F 0.6323(2) -0.09579(12) 0.68486(10) 0.0365(6) Uani 1 1 d . . . . .
F19 F 0.6435(2) 0.10420(11) 0.61694(9) 0.0348(6) Uani 1 1 d . . . . .
F20 F 0.6486(3) 0.22563(12) 0.61508(11) 0.0471(7) Uani 1 1 d . . . . .
F21 F 0.4519(3) 0.29040(11) 0.61125(11) 0.0508(7) Uani 1 1 d . . . . .
F22 F 0.2434(3) 0.23535(12) 0.60329(11) 0.0470(7) Uani 1 1 d . . . . .
F23 F -0.1144(2) 0.15041(13) 0.65823(11) 0.0464(7) Uani 1 1 d . . . . .
F24 F -0.2889(2) 0.11350(14) 0.72008(10) 0.0493(7) Uani 1 1 d . . . . .
F25 F -0.3034(2) -0.00104(15) 0.75140(10) 0.0477(7) Uani 1 1 d . . . . .
F26 F -0.1390(2) -0.08364(12) 0.72537(9) 0.0384(6) Uani 1 1 d . . . . .
C49 C 0.2584(3) -0.04785(18) 0.80535(15) 0.0254(9) Uani 1 1 d . . . . .
C50 C 0.4304(4) 0.00252(19) 0.81173(14) 0.0257(9) Uani 1 1 d . . . . .
C51 C 0.4333(4) 0.10510(19) 0.80532(15) 0.0261(9) Uani 1 1 d . . . . .
C52 C 0.2664(4) 0.15655(19) 0.79106(15) 0.0263(9) Uani 1 1 d . . . . .
C53 C 0.0951(3) 0.10650(18) 0.78123(14) 0.0236(8) Uani 1 1 d . . . . .
C54 C 0.0913(3) 0.00386(18) 0.79024(14) 0.0230(8) Uani 1 1 d . . . . .
C55 C 0.5342(4) 0.0235(2) 0.83727(15) 0.0278(9) Uani 1 1 d . . . . .
C56 C 0.5361(4) 0.0873(2) 0.83334(15) 0.0280(9) Uani 1 1 d . . . . .
C57 C 0.1739(4) 0.19857(18) 0.80334(15) 0.0261(9) Uani 1 1 d . . . . .
C58 C 0.0670(4) 0.16756(17) 0.79613(15) 0.0248(8) Uani 1 1 d . . . . .
C59 C 0.0598(4) -0.05191(18) 0.81524(15) 0.0243(8) Uani 1 1 d . . . . .
C60 C 0.1637(4) -0.08404(18) 0.82465(15) 0.0258(9) Uani 1 1 d . . . . .
C61 C 0.6176(4) -0.0067(2) 0.86508(15) 0.0305(9) Uani 1 1 d . . . . .
C62 C 0.7032(4) 0.0266(2) 0.88823(16) 0.0340(10) Uani 1 1 d . . . . .
C63 C 0.7067(4) 0.0894(2) 0.88383(17) 0.0374(11) Uani 1 1 d . . . . .
C64 C 0.6226(4) 0.1195(2) 0.85730(17) 0.0339(10) Uani 1 1 d . . . . .
C65 C 0.1726(4) 0.25563(18) 0.82483(15) 0.0272(9) Uani 1 1 d . . . . .
C66 C 0.0693(4) 0.28188(18) 0.83749(15) 0.0272(9) Uani 1 1 d . . . . .
C67 C -0.0341(4) 0.25189(19) 0.82967(15) 0.0260(9) Uani 1 1 d . . . . .
C68 C -0.0363(3) 0.19499(18) 0.80910(14) 0.0245(8) Uani 1 1 d . . . . .
C69 C -0.0443(4) -0.07385(19) 0.83327(16) 0.0287(9) Uani 1 1 d . . . . .
C70 C -0.0459(4) -0.1275(2) 0.85964(18) 0.0365(10) Uani 1 1 d . . . . .
C71 C 0.0555(4) -0.1593(2) 0.86832(17) 0.0367(10) Uani 1 1 d . . . . .
C72 C 0.1601(4) -0.13773(19) 0.85136(16) 0.0314(10) Uani 1 1 d . . . . .
N13 N 0.2122(3) 0.10625(15) 0.77294(12) 0.0240(7) Uani 1 1 d . . . . .
N14 N 0.0320(3) 0.05617(15) 0.78706(12) 0.0238(7) Uani 1 1 d . . . . .
N15 N 0.2078(3) -0.00020(15) 0.78093(11) 0.0227(7) Uani 1 1 d . . . . .
N16 N 0.3707(3) -0.04883(16) 0.81789(12) 0.0266(8) Uani 1 1 d . . . . .
N17 N 0.3849(3) 0.05220(15) 0.78860(12) 0.0241(7) Uani 1 1 d . . . . .
N18 N 0.3775(3) 0.15830(15) 0.80405(13) 0.0276(7) Uani 1 1 d . . . . .
B3 B 0.2758(4) 0.0507(2) 0.75860(16) 0.0237(9) Uani 1 1 d . . . . .
F27 F 0.2925(2) 0.04461(11) 0.70669(8) 0.0309(5) Uani 1 1 d . . . . .
F28 F 0.2715(2) 0.28499(11) 0.83538(10) 0.0360(6) Uani 1 1 d . . . . .
F29 F 0.0673(2) 0.33617(10) 0.85983(9) 0.0344(6) Uani 1 1 d . . . . .
F30 F -0.1334(2) 0.27736(10) 0.84569(9) 0.0320(5) Uani 1 1 d . . . . .
F31 F -0.1377(2) 0.16619(11) 0.80335(9) 0.0320(5) Uani 1 1 d . . . . .
F32 F -0.1432(2) -0.04403(11) 0.82499(9) 0.0341(6) Uani 1 1 d . . . . .
F33 F -0.1462(2) -0.14953(13) 0.87667(12) 0.0521(7) Uani 1 1 d . . . . .
F34 F 0.0499(3) -0.21151(12) 0.89356(12) 0.0540(8) Uani 1 1 d . . . . .
F35 F 0.2571(2) -0.16875(11) 0.86114(10) 0.0392(6) Uani 1 1 d . . . . .
F36 F 0.6165(2) -0.06679(12) 0.86927(9) 0.0390(6) Uani 1 1 d . . . . .
F37 F 0.7852(2) -0.00103(14) 0.91577(9) 0.0458(7) Uani 1 1 d . . . . .
F38 F 0.7934(2) 0.11872(14) 0.90662(10) 0.0466(7) Uani 1 1 d . . . . .
F39 F 0.6271(2) 0.18026(12) 0.85489(11) 0.0452(7) 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 N2 1.342(5) . ?
C1 N1 1.373(5) . ?
C1 C8 1.453(6) . ?
C2 N2 1.348(5) . ?
C2 N3 1.365(5) . ?
C2 C9 1.455(5) . ?
C3 N4 1.345(5) . ?
C3 N3 1.368(5) . ?
C3 C10 1.445(6) . ?
C4 N4 1.338(5) . ?
C4 N5 1.373(5) . ?
C4 C11 1.443(6) . ?
C5 N6 1.340(5) . ?
C5 N5 1.373(5) . ?
C5 C12 1.448(6) . ?
C6 N6 1.347(5) . ?
C6 N1 1.366(5) . ?
C6 C7 1.449(6) . ?
C7 C13 1.385(6) . ?
C7 C8 1.418(6) . ?
C8 C16 1.380(6) . ?
C9 C17 1.382(6) . ?
C9 C10 1.418(6) . ?
C10 C20 1.391(6) . ?
C11 C21 1.391(5) . ?
C11 C12 1.416(5) . ?
C12 C24 1.379(6) . ?
C13 F2 1.346(5) . ?
C13 C14 1.368(6) . ?
C14 F3 1.334(5) . ?
C14 C15 1.392(7) . ?
C15 F4 1.341(5) . ?
C15 C16 1.371(6) . ?
C16 F5 1.338(5) . ?
C17 F6 1.346(5) . ?
C17 C18 1.370(6) . ?
C18 F7 1.346(5) . ?
C18 C19 1.383(6) . ?
C19 F8 1.343(5) . ?
C19 C20 1.372(6) . ?
C20 F9 1.346(5) . ?
C21 F10 1.343(4) . ?
C21 C22 1.370(6) . ?
C22 F11 1.346(4) . ?
C22 C23 1.385(6) . ?
C23 F12 1.340(5) . ?
C23 C24 1.374(5) . ?
C24 F13 1.342(4) . ?
N1 B1 1.489(5) . ?
N3 B1 1.490(5) . ?
N5 B1 1.480(6) . ?
B1 F1 1.390(5) . ?
C25 N8 1.348(5) . ?
C25 N7 1.371(5) . ?
C25 C32 1.447(6) . ?
C26 N8 1.335(5) . ?
C26 N9 1.369(5) . ?
C26 C33 1.463(6) . ?
C27 N10 1.339(5) . ?
C27 N9 1.372(5) . ?
C27 C34 1.445(6) . ?
C28 N10 1.339(6) . ?
C28 N11 1.370(5) . ?
C28 C35 1.454(6) . ?
C29 N12 1.339(5) . ?
C29 N11 1.361(5) . ?
C29 C36 1.452(6) . ?
C30 N12 1.348(5) . ?
C30 N7 1.362(5) . ?
C30 C31 1.452(6) . ?
C31 C37 1.388(6) . ?
C31 C32 1.423(6) . ?
C32 C40 1.385(6) . ?
C33 C41 1.382(6) . ?
C33 C34 1.428(6) . ?
C34 C44 1.379(6) . ?
C35 C45 1.385(6) . ?
C35 C36 1.421(6) . ?
C36 C48 1.388(6) . ?
C37 F15 1.343(5) . ?
C37 C38 1.367(6) . ?
C38 F16 1.336(5) . ?
C38 C39 1.390(7) . ?
C39 F17 1.341(5) . ?
C39 C40 1.374(6) . ?
C40 F18 1.337(5) . ?
C41 F19 1.339(5) . ?
C41 C42 1.368(6) . ?
C42 F20 1.340(5) . ?
C42 C43 1.387(7) . ?
C43 F21 1.346(5) . ?
C43 C44 1.365(7) . ?
C44 F22 1.346(5) . ?
C45 F23 1.347(5) . ?
C45 C46 1.371(7) . ?
C46 F24 1.351(5) . ?
C46 C47 1.392(7) . ?
C47 F25 1.339(5) . ?
C47 C48 1.372(6) . ?
C48 F26 1.337(5) . ?
N7 B2 1.487(5) . ?
N9 B2 1.482(6) . ?
N11 B2 1.487(5) . ?
B2 F14 1.395(5) . ?
C49 N16 1.339(5) . ?
C49 N15 1.368(5) . ?
C49 C60 1.449(6) . ?
C50 N16 1.341(6) . ?
C50 N17 1.364(5) . ?
C50 C55 1.453(6) . ?
C51 N18 1.345(5) . ?
C51 N17 1.372(5) . ?
C51 C56 1.454(6) . ?
C52 N18 1.330(5) . ?
C52 N13 1.365(5) . ?
C52 C57 1.454(6) . ?
C53 N14 1.342(5) . ?
C53 N13 1.370(5) . ?
C53 C58 1.446(6) . ?
C54 N14 1.349(5) . ?
C54 N15 1.371(5) . ?
C54 C59 1.448(6) . ?
C55 C61 1.383(6) . ?
C55 C56 1.419(6) . ?
C56 C64 1.381(6) . ?
C57 C65 1.386(6) . ?
C57 C58 1.426(6) . ?
C58 C68 1.383(6) . ?
C59 C69 1.382(6) . ?
C59 C60 1.418(6) . ?
C60 C72 1.383(6) . ?
C61 F36 1.337(5) . ?
C61 C62 1.377(6) . ?
C62 F37 1.341(5) . ?
C62 C63 1.397(7) . ?
C63 F38 1.337(5) . ?
C63 C64 1.372(7) . ?
C64 F39 1.349(5) . ?
C65 F28 1.344(5) . ?
C65 C66 1.369(6) . ?
C66 F29 1.340(5) . ?
C66 C67 1.383(6) . ?
C67 F30 1.347(5) . ?
C67 C68 1.373(6) . ?
C68 F31 1.343(5) . ?
C69 F32 1.339(5) . ?
C69 C70 1.378(6) . ?
C70 F33 1.334(5) . ?
C70 C71 1.387(7) . ?
C71 F34 1.337(5) . ?
C71 C72 1.374(7) . ?
C72 F35 1.340(5) . ?
N13 B3 1.484(6) . ?
N15 B3 1.495(6) . ?
N17 B3 1.489(6) . ?
B3 F27 1.388(5) . ?

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
N2 C1 N1 123.0(4) . . ?
N2 C1 C8 129.3(4) . . ?
N1 C1 C8 105.8(3) . . ?
N2 C2 N3 122.9(3) . . ?
N2 C2 C9 129.1(4) . . ?
N3 C2 C9 105.8(3) . . ?
N4 C3 N3 123.1(3) . . ?
N4 C3 C10 129.9(3) . . ?
N3 C3 C10 105.6(3) . . ?
N4 C4 N5 122.9(4) . . ?
N4 C4 C11 129.9(4) . . ?
N5 C4 C11 105.7(3) . . ?
N6 C5 N5 122.8(4) . . ?
N6 C5 C12 129.3(4) . . ?
N5 C5 C12 105.9(3) . . ?
N6 C6 N1 123.4(4) . . ?
N6 C6 C7 129.0(4) . . ?
N1 C6 C7 105.9(3) . . ?
C13 C7 C8 119.5(4) . . ?
C13 C7 C6 132.7(4) . . ?
C8 C7 C6 107.5(3) . . ?
C16 C8 C7 120.2(4) . . ?
C16 C8 C1 132.6(4) . . ?
C7 C8 C1 107.0(3) . . ?
C17 C9 C10 121.1(4) . . ?
C17 C9 C2 132.2(4) . . ?
C10 C9 C2 106.6(3) . . ?
C20 C10 C9 118.9(4) . . ?
C20 C10 C3 133.3(4) . . ?
C9 C10 C3 107.7(3) . . ?
C21 C11 C12 119.1(4) . . ?
C21 C11 C4 133.1(4) . . ?
C12 C11 C4 107.6(3) . . ?
C24 C12 C11 120.5(4) . . ?
C24 C12 C5 132.2(4) . . ?
C11 C12 C5 107.0(3) . . ?
F2 C13 C14 119.5(4) . . ?
F2 C13 C7 120.9(4) . . ?
C14 C13 C7 119.6(4) . . ?
F3 C14 C13 120.4(4) . . ?
F3 C14 C15 119.0(4) . . ?
C13 C14 C15 120.6(4) . . ?
F4 C15 C16 120.4(4) . . ?
F4 C15 C14 118.6(4) . . ?
C16 C15 C14 121.0(4) . . ?
F5 C16 C15 119.9(4) . . ?
F5 C16 C8 121.1(4) . . ?
C15 C16 C8 119.1(4) . . ?
F6 C17 C18 120.6(4) . . ?
F6 C17 C9 121.0(4) . . ?
C18 C17 C9 118.4(4) . . ?
F7 C18 C17 120.6(4) . . ?
F7 C18 C19 118.1(4) . . ?
C17 C18 C19 121.3(4) . . ?
F8 C19 C20 120.2(4) . . ?
F8 C19 C18 118.7(4) . . ?
C20 C19 C18 121.1(4) . . ?
F9 C20 C19 119.7(4) . . ?
F9 C20 C10 121.0(4) . . ?
C19 C20 C10 119.2(4) . . ?
F10 C21 C22 119.7(3) . . ?
F10 C21 C11 121.2(4) . . ?
C22 C21 C11 119.2(4) . . ?
F11 C22 C21 119.6(4) . . ?
F11 C22 C23 119.0(4) . . ?
C21 C22 C23 121.4(3) . . ?
F12 C23 C24 120.4(4) . . ?
F12 C23 C22 119.2(3) . . ?
C24 C23 C22 120.4(4) . . ?
F13 C24 C23 119.9(3) . . ?
F13 C24 C12 120.8(3) . . ?
C23 C24 C12 119.3(4) . . ?
C6 N1 C1 112.6(3) . . ?
C6 N1 B1 122.5(3) . . ?
C1 N1 B1 122.9(3) . . ?
C1 N2 C2 116.5(3) . . ?
C2 N3 C3 112.6(3) . . ?
C2 N3 B1 122.8(3) . . ?
C3 N3 B1 123.0(3) . . ?
C4 N4 C3 116.7(3) . . ?
C5 N5 C4 111.9(3) . . ?
C5 N5 B1 122.8(3) . . ?
C4 N5 B1 123.3(3) . . ?
C5 N6 C6 116.4(3) . . ?
F1 B1 N5 113.3(3) . . ?
F1 B1 N1 113.5(3) . . ?
N5 B1 N1 105.3(3) . . ?
F1 B1 N3 114.0(3) . . ?
N5 B1 N3 105.2(3) . . ?
N1 B1 N3 104.6(3) . . ?
N8 C25 N7 122.8(4) . . ?
N8 C25 C32 129.8(4) . . ?
N7 C25 C32 105.5(3) . . ?
N8 C26 N9 123.8(4) . . ?
N8 C26 C33 129.5(4) . . ?
N9 C26 C33 105.0(3) . . ?
N10 C27 N9 122.7(4) . . ?
N10 C27 C34 130.0(4) . . ?
N9 C27 C34 105.6(3) . . ?
N10 C28 N11 123.0(4) . . ?
N10 C28 C35 130.2(4) . . ?
N11 C28 C35 105.4(4) . . ?
N12 C29 N11 123.1(4) . . ?
N12 C29 C36 129.7(4) . . ?
N11 C29 C36 105.3(4) . . ?
N12 C30 N7 122.8(4) . . ?
N12 C30 C31 130.0(4) . . ?
N7 C30 C31 105.8(3) . . ?
C37 C31 C32 119.1(4) . . ?
C37 C31 C30 133.9(4) . . ?
C32 C31 C30 106.9(3) . . ?
C40 C32 C31 120.3(4) . . ?
C40 C32 C25 132.2(4) . . ?
C31 C32 C25 107.4(3) . . ?
C41 C33 C34 119.9(4) . . ?
C41 C33 C26 132.8(4) . . ?
C34 C33 C26 107.1(3) . . ?
C44 C34 C33 119.2(4) . . ?
C44 C34 C27 133.3(4) . . ?
C33 C34 C27 107.4(3) . . ?
C45 C35 C36 119.8(4) . . ?
C45 C35 C28 133.0(4) . . ?
C36 C35 C28 107.1(3) . . ?
C48 C36 C35 120.1(4) . . ?
C48 C36 C29 132.5(4) . . ?
C35 C36 C29 107.3(4) . . ?
F15 C37 C38 119.0(4) . . ?
F15 C37 C31 121.2(4) . . ?
C38 C37 C31 119.8(4) . . ?
F16 C38 C37 120.5(4) . . ?
F16 C38 C39 118.6(4) . . ?
C37 C38 C39 120.9(4) . . ?
F17 C39 C40 120.7(4) . . ?
F17 C39 C38 118.5(4) . . ?
C40 C39 C38 120.8(4) . . ?
F18 C40 C39 120.1(4) . . ?
F18 C40 C32 120.8(4) . . ?
C39 C40 C32 119.1(4) . . ?
F19 C41 C42 119.5(4) . . ?
F19 C41 C33 121.2(4) . . ?
C42 C41 C33 119.4(4) . . ?
F20 C42 C41 119.8(4) . . ?
F20 C42 C43 119.5(4) . . ?
C41 C42 C43 120.7(4) . . ?
F21 C43 C44 120.4(4) . . ?
F21 C43 C42 118.5(4) . . ?
C44 C43 C42 121.1(4) . . ?
F22 C44 C43 119.5(4) . . ?
F22 C44 C34 120.8(4) . . ?
C43 C44 C34 119.7(4) . . ?
F23 C45 C46 119.9(4) . . ?
F23 C45 C35 121.1(4) . . ?
C46 C45 C35 119.0(4) . . ?
F24 C46 C45 120.0(5) . . ?
F24 C46 C47 118.6(4) . . ?
C45 C46 C47 121.3(4) . . ?
F25 C47 C48 120.9(4) . . ?
F25 C47 C46 118.4(4) . . ?
C48 C47 C46 120.7(4) . . ?
F26 C48 C47 119.9(4) . . ?
F26 C48 C36 121.1(4) . . ?
C47 C48 C36 119.0(4) . . ?
C30 N7 C25 112.8(3) . . ?
C30 N7 B2 123.0(3) . . ?
C25 N7 B2 122.4(3) . . ?
C26 N8 C25 116.4(3) . . ?
C26 N9 C27 113.4(3) . . ?
C26 N9 B2 122.0(3) . . ?
C27 N9 B2 122.8(3) . . ?
C27 N10 C28 117.1(3) . . ?
C29 N11 C28 113.2(3) . . ?
C29 N11 B2 122.7(3) . . ?
C28 N11 B2 122.6(3) . . ?
C29 N12 C30 116.6(3) . . ?
F14 B2 N9 113.3(3) . . ?
F14 B2 N7 113.0(3) . . ?
N9 B2 N7 105.7(3) . . ?
F14 B2 N11 113.6(3) . . ?
N9 B2 N11 105.4(3) . . ?
N7 B2 N11 105.0(3) . . ?
N16 C49 N15 122.9(4) . . ?
N16 C49 C60 129.5(4) . . ?
N15 C49 C60 105.6(3) . . ?
N16 C50 N17 122.7(4) . . ?
N16 C50 C55 129.8(4) . . ?
N17 C50 C55 105.5(4) . . ?
N18 C51 N17 123.1(4) . . ?
N18 C51 C56 130.0(4) . . ?
N17 C51 C56 105.4(4) . . ?
N18 C52 N13 123.9(4) . . ?
N18 C52 C57 129.4(4) . . ?
N13 C52 C57 105.3(3) . . ?
N14 C53 N13 123.5(4) . . ?
N14 C53 C58 128.7(4) . . ?
N13 C53 C58 105.6(3) . . ?
N14 C54 N15 122.9(4) . . ?
N14 C54 C59 129.4(4) . . ?
N15 C54 C59 105.8(3) . . ?
C61 C55 C56 120.7(4) . . ?
C61 C55 C50 131.8(4) . . ?
C56 C55 C50 107.3(4) . . ?
C64 C56 C55 119.6(4) . . ?
C64 C56 C51 133.1(4) . . ?
C55 C56 C51 107.1(4) . . ?
C65 C57 C58 119.0(4) . . ?
C65 C57 C52 133.1(4) . . ?
C58 C57 C52 107.4(3) . . ?
C68 C58 C57 120.2(4) . . ?
C68 C58 C53 132.3(4) . . ?
C57 C58 C53 107.0(4) . . ?
C69 C59 C60 120.0(4) . . ?
C69 C59 C54 132.5(4) . . ?
C60 C59 C54 107.2(4) . . ?
C72 C60 C59 119.7(4) . . ?
C72 C60 C49 132.6(4) . . ?
C59 C60 C49 107.5(3) . . ?
F36 C61 C62 120.2(4) . . ?
F36 C61 C55 121.3(4) . . ?
C62 C61 C55 118.5(4) . . ?
F37 C62 C61 120.3(4) . . ?
F37 C62 C63 118.6(4) . . ?
C61 C62 C63 121.2(4) . . ?
F38 C63 C64 121.5(4) . . ?
F38 C63 C62 118.0(4) . . ?
C64 C63 C62 120.5(4) . . ?
F39 C64 C63 118.9(4) . . ?
F39 C64 C56 121.5(4) . . ?
C63 C64 C56 119.6(4) . . ?
F28 C65 C66 119.0(4) . . ?
F28 C65 C57 121.1(4) . . ?
C66 C65 C57 119.8(4) . . ?
F29 C66 C65 120.3(4) . . ?
F29 C66 C67 118.8(4) . . ?
C65 C66 C67 120.9(4) . . ?
F30 C67 C68 119.6(4) . . ?
F30 C67 C66 119.2(4) . . ?
C68 C67 C66 121.1(4) . . ?
F31 C68 C67 119.8(4) . . ?
F31 C68 C58 121.1(4) . . ?
C67 C68 C58 119.1(4) . . ?
F32 C69 C70 119.8(4) . . ?
F32 C69 C59 120.9(4) . . ?
C70 C69 C59 119.3(4) . . ?
F33 C70 C69 119.8(4) . . ?
F33 C70 C71 119.6(4) . . ?
C69 C70 C71 120.6(4) . . ?
F34 C71 C72 120.4(4) . . ?
F34 C71 C70 118.7(4) . . ?
C72 C71 C70 120.9(4) . . ?
F35 C72 C71 119.6(4) . . ?
F35 C72 C60 121.0(4) . . ?
C71 C72 C60 119.4(4) . . ?
C52 N13 C53 113.2(3) . . ?
C52 N13 B3 122.7(4) . . ?
C53 N13 B3 122.2(4) . . ?
C53 N14 C54 116.5(3) . . ?
C49 N15 C54 112.7(3) . . ?
C49 N15 B3 122.9(4) . . ?
C54 N15 B3 122.5(4) . . ?
C49 N16 C50 117.1(4) . . ?
C50 N17 C51 112.9(3) . . ?
C50 N17 B3 123.1(3) . . ?
C51 N17 B3 122.4(3) . . ?
C52 N18 C51 116.4(4) . . ?
F27 B3 N13 113.6(3) . . ?
F27 B3 N17 114.1(4) . . ?
N13 B3 N17 105.4(3) . . ?
F27 B3 N15 112.8(3) . . ?
N13 B3 N15 105.4(3) . . ?
N17 B3 N15 104.7(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 C6 C7 C13 -14.7(7) . . . . ?
N1 C6 C7 C13 180.0(4) . . . . ?
N6 C6 C7 C8 159.2(4) . . . . ?
N1 C6 C7 C8 -6.1(4) . . . . ?
C13 C7 C8 C16 -0.7(6) . . . . ?
C6 C7 C8 C16 -175.5(4) . . . . ?
C13 C7 C8 C1 174.4(4) . . . . ?
C6 C7 C8 C1 -0.4(4) . . . . ?
N2 C1 C8 C16 16.7(7) . . . . ?
N1 C1 C8 C16 -179.0(4) . . . . ?
N2 C1 C8 C7 -157.6(4) . . . . ?
N1 C1 C8 C7 6.8(4) . . . . ?
N2 C2 C9 C17 -21.2(7) . . . . ?
N3 C2 C9 C17 175.5(4) . . . . ?
N2 C2 C9 C10 154.9(4) . . . . ?
N3 C2 C9 C10 -8.5(4) . . . . ?
C17 C9 C10 C20 1.6(6) . . . . ?
C2 C9 C10 C20 -175.0(4) . . . . ?
C17 C9 C10 C3 177.7(4) . . . . ?
C2 C9 C10 C3 1.1(4) . . . . ?
N4 C3 C10 C20 15.3(7) . . . . ?
N3 C3 C10 C20 -178.1(4) . . . . ?
N4 C3 C10 C9 -160.1(4) . . . . ?
N3 C3 C10 C9 6.6(4) . . . . ?
N4 C4 C11 C21 -16.2(7) . . . . ?
N5 C4 C11 C21 177.7(4) . . . . ?
N4 C4 C11 C12 158.6(4) . . . . ?
N5 C4 C11 C12 -7.5(4) . . . . ?
C21 C11 C12 C24 0.8(6) . . . . ?
C4 C11 C12 C24 -174.9(4) . . . . ?
C21 C11 C12 C5 174.9(3) . . . . ?
C4 C11 C12 C5 -0.7(4) . . . . ?
N6 C5 C12 C24 17.9(7) . . . . ?
N5 C5 C12 C24 -178.1(4) . . . . ?
N6 C5 C12 C11 -155.3(4) . . . . ?
N5 C5 C12 C11 8.7(4) . . . . ?
C8 C7 C13 F2 179.5(3) . . . . ?
C6 C7 C13 F2 -7.2(7) . . . . ?
C8 C7 C13 C14 1.2(6) . . . . ?
C6 C7 C13 C14 174.5(4) . . . . ?
F2 C13 C14 F3 -0.6(6) . . . . ?
C7 C13 C14 F3 177.7(4) . . . . ?
F2 C13 C14 C15 -178.9(4) . . . . ?
C7 C13 C14 C15 -0.5(7) . . . . ?
F3 C14 C15 F4 -0.8(7) . . . . ?
C13 C14 C15 F4 177.5(4) . . . . ?
F3 C14 C15 C16 -179.0(4) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
F4 C15 C16 F5 2.1(6) . . . . ?
C14 C15 C16 F5 -179.7(4) . . . . ?
F4 C15 C16 C8 -177.0(4) . . . . ?
C14 C15 C16 C8 1.2(7) . . . . ?
C7 C8 C16 F5 -179.5(4) . . . . ?
C1 C8 C16 F5 6.8(7) . . . . ?
C7 C8 C16 C15 -0.5(6) . . . . ?
C1 C8 C16 C15 -174.2(4) . . . . ?
C10 C9 C17 F6 179.3(3) . . . . ?
C2 C9 C17 F6 -5.1(7) . . . . ?
C10 C9 C17 C18 0.1(6) . . . . ?
C2 C9 C17 C18 175.6(4) . . . . ?
F6 C17 C18 F7 0.0(6) . . . . ?
C9 C17 C18 F7 179.3(4) . . . . ?
F6 C17 C18 C19 178.9(4) . . . . ?
C9 C17 C18 C19 -1.8(6) . . . . ?
F7 C18 C19 F8 -0.3(6) . . . . ?
C17 C18 C19 F8 -179.2(4) . . . . ?
F7 C18 C19 C20 -179.1(4) . . . . ?
C17 C18 C19 C20 2.0(6) . . . . ?
F8 C19 C20 F9 -0.1(6) . . . . ?
C18 C19 C20 F9 178.7(4) . . . . ?
F8 C19 C20 C10 -179.1(4) . . . . ?
C18 C19 C20 C10 -0.3(6) . . . . ?
C9 C10 C20 F9 179.6(4) . . . . ?
C3 C10 C20 F9 4.6(7) . . . . ?
C9 C10 C20 C19 -1.4(6) . . . . ?
C3 C10 C20 C19 -176.4(4) . . . . ?
C12 C11 C21 F10 -178.0(3) . . . . ?
C4 C11 C21 F10 -3.7(7) . . . . ?
C12 C11 C21 C22 1.4(6) . . . . ?
C4 C11 C21 C22 175.7(4) . . . . ?
F10 C21 C22 F11 -2.4(5) . . . . ?
C11 C21 C22 F11 178.2(3) . . . . ?
F10 C21 C22 C23 176.4(4) . . . . ?
C11 C21 C22 C23 -3.0(6) . . . . ?
F11 C22 C23 F12 3.3(5) . . . . ?
C21 C22 C23 F12 -175.5(3) . . . . ?
F11 C22 C23 C24 -178.7(3) . . . . ?
C21 C22 C23 C24 2.5(6) . . . . ?
F12 C23 C24 F13 -2.2(5) . . . . ?
C22 C23 C24 F13 179.9(3) . . . . ?
F12 C23 C24 C12 177.7(3) . . . . ?
C22 C23 C24 C12 -0.3(6) . . . . ?
C11 C12 C24 F13 178.5(3) . . . . ?
C5 C12 C24 F13 6.1(6) . . . . ?
C11 C12 C24 C23 -1.3(6) . . . . ?
C5 C12 C24 C23 -173.8(4) . . . . ?
N6 C6 N1 C1 -155.4(4) . . . . ?
C7 C6 N1 C1 11.0(4) . . . . ?
N6 C6 N1 B1 8.8(6) . . . . ?
C7 C6 N1 B1 175.2(3) . . . . ?
N2 C1 N1 C6 154.3(4) . . . . ?
C8 C1 N1 C6 -11.3(4) . . . . ?
N2 C1 N1 B1 -9.8(6) . . . . ?
C8 C1 N1 B1 -175.4(3) . . . . ?
N1 C1 N2 C2 -9.5(5) . . . . ?
C8 C1 N2 C2 152.5(4) . . . . ?
N3 C2 N2 C1 7.3(5) . . . . ?
C9 C2 N2 C1 -153.5(4) . . . . ?
N2 C2 N3 C3 -151.2(4) . . . . ?
C9 C2 N3 C3 13.4(4) . . . . ?
N2 C2 N3 B1 14.4(5) . . . . ?
C9 C2 N3 B1 179.0(3) . . . . ?
N4 C3 N3 C2 155.2(4) . . . . ?
C10 C3 N3 C2 -12.6(4) . . . . ?
N4 C3 N3 B1 -10.4(6) . . . . ?
C10 C3 N3 B1 -178.2(3) . . . . ?
N5 C4 N4 C3 7.9(5) . . . . ?
C11 C4 N4 C3 -156.1(4) . . . . ?
N3 C3 N4 C4 -8.0(5) . . . . ?
C10 C3 N4 C4 156.6(4) . . . . ?
N6 C5 N5 C4 151.2(4) . . . . ?
C12 C5 N5 C4 -14.1(4) . . . . ?
N6 C5 N5 B1 -13.3(6) . . . . ?
C12 C5 N5 B1 -178.6(3) . . . . ?
N4 C4 N5 C5 -153.6(4) . . . . ?
C11 C4 N5 C5 13.7(4) . . . . ?
N4 C4 N5 B1 10.8(6) . . . . ?
C11 C4 N5 B1 178.1(3) . . . . ?
N5 C5 N6 C6 -7.8(5) . . . . ?
C12 C5 N6 C6 153.8(4) . . . . ?
N1 C6 N6 C5 10.0(5) . . . . ?
C7 C6 N6 C5 -153.1(4) . . . . ?
C5 N5 B1 F1 -97.0(4) . . . . ?
C4 N5 B1 F1 100.3(4) . . . . ?
C5 N5 B1 N1 27.6(5) . . . . ?
C4 N5 B1 N1 -135.1(3) . . . . ?
C5 N5 B1 N3 137.8(3) . . . . ?
C4 N5 B1 N3 -24.9(5) . . . . ?
C6 N1 B1 F1 99.1(4) . . . . ?
C1 N1 B1 F1 -98.3(4) . . . . ?
C6 N1 B1 N5 -25.4(5) . . . . ?
C1 N1 B1 N5 137.2(3) . . . . ?
C6 N1 B1 N3 -136.0(4) . . . . ?
C1 N1 B1 N3 26.6(5) . . . . ?
C2 N3 B1 F1 95.8(4) . . . . ?
C3 N3 B1 F1 -100.1(4) . . . . ?
C2 N3 B1 N5 -139.4(3) . . . . ?
C3 N3 B1 N5 24.7(5) . . . . ?
C2 N3 B1 N1 -28.8(5) . . . . ?
C3 N3 B1 N1 135.4(4) . . . . ?
N12 C30 C31 C37 16.2(7) . . . . ?
N7 C30 C31 C37 -177.0(4) . . . . ?
N12 C30 C31 C32 -159.0(4) . . . . ?
N7 C30 C31 C32 7.8(4) . . . . ?
C37 C31 C32 C40 0.0(6) . . . . ?
C30 C31 C32 C40 176.0(4) . . . . ?
C37 C31 C32 C25 -176.6(4) . . . . ?
C30 C31 C32 C25 -0.6(4) . . . . ?
N8 C25 C32 C40 -18.1(7) . . . . ?
N7 C25 C32 C40 177.2(4) . . . . ?
N8 C25 C32 C31 157.9(4) . . . . ?
N7 C25 C32 C31 -6.8(4) . . . . ?
N8 C26 C33 C41 18.0(7) . . . . ?
N9 C26 C33 C41 -176.9(4) . . . . ?
N8 C26 C33 C34 -157.4(4) . . . . ?
N9 C26 C33 C34 7.7(4) . . . . ?
C41 C33 C34 C44 -0.7(6) . . . . ?
C26 C33 C34 C44 175.4(4) . . . . ?
C41 C33 C34 C27 -176.6(4) . . . . ?
C26 C33 C34 C27 -0.5(4) . . . . ?
N10 C27 C34 C44 -16.9(8) . . . . ?
N9 C27 C34 C44 178.0(4) . . . . ?
N10 C27 C34 C33 158.2(4) . . . . ?
N9 C27 C34 C33 -6.9(4) . . . . ?
N10 C28 C35 C45 14.9(8) . . . . ?
N11 C28 C35 C45 -179.0(4) . . . . ?
N10 C28 C35 C36 -160.7(4) . . . . ?
N11 C28 C35 C36 5.4(4) . . . . ?
C45 C35 C36 C48 2.5(6) . . . . ?
C28 C35 C36 C48 178.8(4) . . . . ?
C45 C35 C36 C29 -173.8(4) . . . . ?
C28 C35 C36 C29 2.5(4) . . . . ?
N12 C29 C36 C48 -20.7(7) . . . . ?
N11 C29 C36 C48 174.8(4) . . . . ?
N12 C29 C36 C35 155.0(4) . . . . ?
N11 C29 C36 C35 -9.6(4) . . . . ?
C32 C31 C37 F15 179.5(4) . . . . ?
C30 C31 C37 F15 4.8(7) . . . . ?
C32 C31 C37 C38 -1.3(6) . . . . ?
C30 C31 C37 C38 -176.0(4) . . . . ?
F15 C37 C38 F16 1.4(6) . . . . ?
C31 C37 C38 F16 -177.9(4) . . . . ?
F15 C37 C38 C39 -178.2(4) . . . . ?
C31 C37 C38 C39 2.6(7) . . . . ?
F16 C38 C39 F17 -1.1(6) . . . . ?
C37 C38 C39 F17 178.5(4) . . . . ?
F16 C38 C39 C40 177.9(4) . . . . ?
C37 C38 C39 C40 -2.6(7) . . . . ?
F17 C39 C40 F18 0.4(6) . . . . ?
C38 C39 C40 F18 -178.6(4) . . . . ?
F17 C39 C40 C32 -179.8(4) . . . . ?
C38 C39 C40 C32 1.2(7) . . . . ?
C31 C32 C40 F18 179.8(4) . . . . ?
C25 C32 C40 F18 -4.5(7) . . . . ?
C31 C32 C40 C39 0.0(6) . . . . ?
C25 C32 C40 C39 175.7(4) . . . . ?
C34 C33 C41 F19 179.4(4) . . . . ?
C26 C33 C41 F19 4.4(7) . . . . ?
C34 C33 C41 C42 -2.0(6) . . . . ?
C26 C33 C41 C42 -176.9(4) . . . . ?
F19 C41 C42 F20 1.5(6) . . . . ?
C33 C41 C42 F20 -177.2(4) . . . . ?
F19 C41 C42 C43 -178.1(4) . . . . ?
C33 C41 C42 C43 3.2(7) . . . . ?
F20 C42 C43 F21 -1.5(6) . . . . ?
C41 C42 C43 F21 178.0(4) . . . . ?
F20 C42 C43 C44 178.6(4) . . . . ?
C41 C42 C43 C44 -1.9(7) . . . . ?
F21 C43 C44 F22 0.8(6) . . . . ?
C42 C43 C44 F22 -179.3(4) . . . . ?
F21 C43 C44 C34 179.3(4) . . . . ?
C42 C43 C44 C34 -0.8(7) . . . . ?
C33 C34 C44 F22 -179.5(4) . . . . ?
C27 C34 C44 F22 -4.8(7) . . . . ?
C33 C34 C44 C43 2.1(6) . . . . ?
C27 C34 C44 C43 176.7(4) . . . . ?
C36 C35 C45 F23 178.7(4) . . . . ?
C28 C35 C45 F23 3.6(7) . . . . ?
C36 C35 C45 C46 -2.2(6) . . . . ?
C28 C35 C45 C46 -177.3(4) . . . . ?
F23 C45 C46 F24 -0.2(6) . . . . ?
C35 C45 C46 F24 -179.3(4) . . . . ?
F23 C45 C46 C47 179.4(4) . . . . ?
C35 C45 C46 C47 0.2(7) . . . . ?
F24 C46 C47 F25 0.8(6) . . . . ?
C45 C46 C47 F25 -178.7(4) . . . . ?
F24 C46 C47 C48 -179.1(4) . . . . ?
C45 C46 C47 C48 1.4(7) . . . . ?
F25 C47 C48 F26 -1.0(6) . . . . ?
C46 C47 C48 F26 178.9(4) . . . . ?
F25 C47 C48 C36 179.1(4) . . . . ?
C46 C47 C48 C36 -1.0(6) . . . . ?
C35 C36 C48 F26 179.2(4) . . . . ?
C29 C36 C48 F26 -5.6(7) . . . . ?
C35 C36 C48 C47 -0.9(6) . . . . ?
C29 C36 C48 C47 174.3(4) . . . . ?
N12 C30 N7 C25 155.1(4) . . . . ?
C31 C30 N7 C25 -12.8(4) . . . . ?
N12 C30 N7 B2 -10.1(5) . . . . ?
C31 C30 N7 B2 -178.1(3) . . . . ?
N8 C25 N7 C30 -153.6(4) . . . . ?
C32 C25 N7 C30 12.4(4) . . . . ?
N8 C25 N7 B2 11.7(6) . . . . ?
C32 C25 N7 B2 177.8(3) . . . . ?
N9 C26 N8 C25 -7.9(5) . . . . ?
C33 C26 N8 C25 154.7(4) . . . . ?
N7 C25 N8 C26 7.8(5) . . . . ?
C32 C25 N8 C26 -154.6(4) . . . . ?
N8 C26 N9 C27 153.4(4) . . . . ?
C33 C26 N9 C27 -12.8(4) . . . . ?
N8 C26 N9 B2 -11.7(6) . . . . ?
C33 C26 N9 B2 -177.9(3) . . . . ?
N10 C27 N9 C26 -153.8(4) . . . . ?
C34 C27 N9 C26 12.6(4) . . . . ?
N10 C27 N9 B2 11.1(6) . . . . ?
C34 C27 N9 B2 177.6(3) . . . . ?
N9 C27 N10 C28 8.2(6) . . . . ?
C34 C27 N10 C28 -154.7(4) . . . . ?
N11 C28 N10 C27 -8.1(6) . . . . ?
C35 C28 N10 C27 155.9(4) . . . . ?
N12 C29 N11 C28 -152.0(4) . . . . ?
C36 C29 N11 C28 13.8(4) . . . . ?
N12 C29 N11 B2 14.2(6) . . . . ?
C36 C29 N11 B2 -179.9(3) . . . . ?
N10 C28 N11 C29 155.1(4) . . . . ?
C35 C28 N11 C29 -12.3(4) . . . . ?
N10 C28 N11 B2 -11.1(6) . . . . ?
C35 C28 N11 B2 -178.5(3) . . . . ?
N11 C29 N12 C30 6.1(5) . . . . ?
C36 C29 N12 C30 -156.1(4) . . . . ?
N7 C30 N12 C29 -8.1(5) . . . . ?
C31 C30 N12 C29 156.7(4) . . . . ?
C26 N9 B2 F14 -97.4(4) . . . . ?
C27 N9 B2 F14 98.9(4) . . . . ?
C26 N9 B2 N7 26.9(5) . . . . ?
C27 N9 B2 N7 -136.8(3) . . . . ?
C26 N9 B2 N11 137.7(3) . . . . ?
C27 N9 B2 N11 -26.0(5) . . . . ?
C30 N7 B2 F14 -98.7(4) . . . . ?
C25 N7 B2 F14 97.5(4) . . . . ?
C30 N7 B2 N9 136.9(3) . . . . ?
C25 N7 B2 N9 -26.9(5) . . . . ?
C30 N7 B2 N11 25.7(5) . . . . ?
C25 N7 B2 N11 -138.1(4) . . . . ?
C29 N11 B2 F14 96.4(4) . . . . ?
C28 N11 B2 F14 -98.7(4) . . . . ?
C29 N11 B2 N9 -139.0(3) . . . . ?
C28 N11 B2 N9 25.9(5) . . . . ?
C29 N11 B2 N7 -27.7(5) . . . . ?
C28 N11 B2 N7 137.3(3) . . . . ?
N16 C50 C55 C61 18.4(7) . . . . ?
N17 C50 C55 C61 -177.3(4) . . . . ?
N16 C50 C55 C56 -156.5(4) . . . . ?
N17 C50 C55 C56 7.8(4) . . . . ?
C61 C55 C56 C64 0.4(6) . . . . ?
C50 C55 C56 C64 176.0(4) . . . . ?
C61 C55 C56 C51 -175.6(4) . . . . ?
C50 C55 C56 C51 -0.1(4) . . . . ?
N18 C51 C56 C64 -17.1(8) . . . . ?
N17 C51 C56 C64 177.1(4) . . . . ?
N18 C51 C56 C55 158.2(4) . . . . ?
N17 C51 C56 C55 -7.6(4) . . . . ?
N18 C52 C57 C65 10.8(8) . . . . ?
N13 C52 C57 C65 176.9(4) . . . . ?
N18 C52 C57 C58 -160.5(4) . . . . ?
N13 C52 C57 C58 5.7(4) . . . . ?
C65 C57 C58 C68 1.9(6) . . . . ?
C52 C57 C58 C68 174.6(4) . . . . ?
C65 C57 C58 C53 -170.8(4) . . . . ?
C52 C57 C58 C53 1.9(4) . . . . ?
N14 C53 C58 C68 -17.0(7) . . . . ?
N13 C53 C58 C68 179.9(4) . . . . ?
N14 C53 C58 C57 154.4(4) . . . . ?
N13 C53 C58 C57 -8.7(4) . . . . ?
N14 C54 C59 C69 16.1(7) . . . . ?
N15 C54 C59 C69 -179.5(4) . . . . ?
N14 C54 C59 C60 -158.0(4) . . . . ?
N15 C54 C59 C60 6.4(4) . . . . ?
C69 C59 C60 C72 0.8(6) . . . . ?
C54 C59 C60 C72 175.8(4) . . . . ?
C69 C59 C60 C49 -175.0(4) . . . . ?
C54 C59 C60 C49 0.0(4) . . . . ?
N16 C49 C60 C72 -17.4(8) . . . . ?
N15 C49 C60 C72 178.6(4) . . . . ?
N16 C49 C60 C59 157.7(4) . . . . ?
N15 C49 C60 C59 -6.3(4) . . . . ?
C56 C55 C61 F36 179.7(4) . . . . ?
C50 C55 C61 F36 5.4(7) . . . . ?
C56 C55 C61 C62 -0.9(6) . . . . ?
C50 C55 C61 C62 -175.2(4) . . . . ?
F36 C61 C62 F37 -1.0(6) . . . . ?
C55 C61 C62 F37 179.6(4) . . . . ?
F36 C61 C62 C63 179.2(4) . . . . ?
C55 C61 C62 C63 -0.2(6) . . . . ?
F37 C62 C63 F38 1.3(6) . . . . ?
C61 C62 C63 F38 -178.9(4) . . . . ?
F37 C62 C63 C64 -178.0(4) . . . . ?
C61 C62 C63 C64 1.8(7) . . . . ?
F38 C63 C64 F39 -1.0(6) . . . . ?
C62 C63 C64 F39 178.3(4) . . . . ?
F38 C63 C64 C56 178.5(4) . . . . ?
C62 C63 C64 C56 -2.2(7) . . . . ?
C55 C56 C64 F39 -179.4(4) . . . . ?
C51 C56 C64 F39 -4.6(7) . . . . ?
C55 C56 C64 C63 1.1(6) . . . . ?
C51 C56 C64 C63 176.0(4) . . . . ?
C58 C57 C65 F28 175.7(4) . . . . ?
C52 C57 C65 F28 5.2(7) . . . . ?
C58 C57 C65 C66 -1.7(6) . . . . ?
C52 C57 C65 C66 -172.2(4) . . . . ?
F28 C65 C66 F29 0.3(6) . . . . ?
C57 C65 C66 F29 177.8(4) . . . . ?
F28 C65 C66 C67 -176.7(4) . . . . ?
C57 C65 C66 C67 0.8(6) . . . . ?
F29 C66 C67 F30 -1.5(6) . . . . ?
C65 C66 C67 F30 175.6(4) . . . . ?
F29 C66 C67 C68 -177.0(3) . . . . ?
C65 C66 C67 C68 0.1(6) . . . . ?
F30 C67 C68 F31 2.5(6) . . . . ?
C66 C67 C68 F31 178.0(4) . . . . ?
F30 C67 C68 C58 -175.4(4) . . . . ?
C66 C67 C68 C58 0.0(6) . . . . ?
C57 C58 C68 F31 -178.9(4) . . . . ?
C53 C58 C68 F31 -8.4(7) . . . . ?
C57 C58 C68 C67 -1.0(6) . . . . ?
C53 C58 C68 C67 169.5(4) . . . . ?
C60 C59 C69 F32 179.7(3) . . . . ?
C54 C59 C69 F32 6.2(7) . . . . ?
C60 C59 C69 C70 -1.0(6) . . . . ?
C54 C59 C69 C70 -174.6(4) . . . . ?
F32 C69 C70 F33 0.1(6) . . . . ?
C59 C69 C70 F33 -179.2(4) . . . . ?
F32 C69 C70 C71 179.6(4) . . . . ?
C59 C69 C70 C71 0.3(7) . . . . ?
F33 C70 C71 F34 0.2(7) . . . . ?
C69 C70 C71 F34 -179.2(4) . . . . ?
F33 C70 C71 C72 -179.9(4) . . . . ?
C69 C70 C71 C72 0.7(7) . . . . ?
F34 C71 C72 F35 -1.4(6) . . . . ?
C70 C71 C72 F35 178.7(4) . . . . ?
F34 C71 C72 C60 179.0(4) . . . . ?
C70 C71 C72 C60 -0.9(7) . . . . ?
C59 C60 C72 F35 -179.5(4) . . . . ?
C49 C60 C72 F35 -4.8(7) . . . . ?
C59 C60 C72 C71 0.2(6) . . . . ?
C49 C60 C72 C71 174.8(4) . . . . ?
N18 C52 N13 C53 155.2(4) . . . . ?
C57 C52 N13 C53 -11.9(4) . . . . ?
N18 C52 N13 B3 -9.4(6) . . . . ?
C57 C52 N13 B3 -176.5(3) . . . . ?
N14 C53 N13 C52 -151.1(4) . . . . ?
C58 C53 N13 C52 13.1(4) . . . . ?
N14 C53 N13 B3 13.6(6) . . . . ?
C58 C53 N13 B3 177.8(3) . . . . ?
N13 C53 N14 C54 7.4(5) . . . . ?
C58 C53 N14 C54 -153.0(4) . . . . ?
N15 C54 N14 C53 -9.1(5) . . . . ?
C59 C54 N14 C53 153.0(4) . . . . ?
N16 C49 N15 C54 -154.4(4) . . . . ?
C60 C49 N15 C54 11.0(4) . . . . ?
N16 C49 N15 B3 10.1(6) . . . . ?
C60 C49 N15 B3 175.5(3) . . . . ?
N14 C54 N15 C49 154.7(4) . . . . ?
C59 C54 N15 C49 -11.0(4) . . . . ?
N14 C54 N15 B3 -9.9(5) . . . . ?
C59 C54 N15 B3 -175.6(3) . . . . ?
N15 C49 N16 C50 8.7(6) . . . . ?
C60 C49 N16 C50 -152.9(4) . . . . ?
N17 C50 N16 C49 -7.2(5) . . . . ?
C55 C50 N16 C49 154.7(4) . . . . ?
N16 C50 N17 C51 152.3(4) . . . . ?
C55 C50 N17 C51 -13.4(4) . . . . ?
N16 C50 N17 B3 -13.3(6) . . . . ?
C55 C50 N17 B3 -179.0(3) . . . . ?
N18 C51 N17 C50 -153.7(4) . . . . ?
C56 C51 N17 C50 13.4(4) . . . . ?
N18 C51 N17 B3 12.1(6) . . . . ?
C56 C51 N17 B3 179.1(3) . . . . ?
N13 C52 N18 C51 -9.0(6) . . . . ?
C57 C52 N18 C51 154.8(4) . . . . ?
N17 C51 N18 C52 7.6(6) . . . . ?
C56 C51 N18 C52 -156.0(4) . . . . ?
C52 N13 B3 F27 -100.8(4) . . . . ?
C53 N13 B3 F27 96.0(4) . . . . ?
C52 N13 B3 N17 24.8(5) . . . . ?
C53 N13 B3 N17 -138.4(4) . . . . ?
C52 N13 B3 N15 135.2(4) . . . . ?
C53 N13 B3 N15 -28.0(5) . . . . ?
C50 N17 B3 F27 -96.5(4) . . . . ?
C51 N17 B3 F27 99.2(4) . . . . ?
C50 N17 B3 N13 138.2(4) . . . . ?
C51 N17 B3 N13 -26.0(5) . . . . ?
C50 N17 B3 N15 27.3(5) . . . . ?
C51 N17 B3 N15 -136.9(3) . . . . ?
C49 N15 B3 F27 98.9(4) . . . . ?
C54 N15 B3 F27 -98.2(4) . . . . ?
C49 N15 B3 N13 -136.7(4) . . . . ?
C54 N15 B3 N13 26.3(5) . . . . ?
C49 N15 B3 N17 -25.8(5) . . . . ?
C54 N15 B3 N17 137.2(3) . . . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method Sublimation
