# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_p-10
_database_code_depnum_ccdc_archive 'CCDC 1401466'
_audit_update_record             
;
2015-06-18 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 B2 F4 N8'
_chemical_formula_weight         618.21
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.492(2)
_cell_length_b                   14.163(3)
_cell_length_c                   15.253(3)
_cell_angle_alpha                65.150(6)
_cell_angle_beta                 69.157(9)
_cell_angle_gamma                82.705(8)
_cell_volume                     2104.6(7)
_cell_formula_units_Z            3
_cell_measurement_temperature    110
_cell_measurement_reflns_used    4561
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      66.78
_exptl_crystal_description       Prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             954
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.905
_shelx_estimated_absorpt_T_min   0.650
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6265
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Nonius KappaCCD Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26066
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.727
_diffrn_reflns_theta_max         66.711
_diffrn_reflns_theta_full        66.711
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             7263
_reflns_number_gt                5550
_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
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_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)+(0.0660P)²+0.2947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7263
_refine_ls_number_parameters     766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
F1 F 0.44535(10) 0.15195(9) 0.68322(9) 0.0329(3) Uani 1 1 d . . . . .
F2 F 0.48272(10) 0.32708(9) 0.59994(8) 0.0342(3) Uani 1 1 d . . . . .
F3 F 0.59295(12) 0.30682(11) 1.37434(9) 0.0442(3) Uani 1 1 d . . . . .
F4 F 0.61745(11) 0.47360(12) 1.35360(11) 0.0473(4) Uani 1 1 d . . . . .
F1A F 1.04379(11) 0.19236(12) 0.31121(10) 0.0458(3) Uani 1 1 d . . . . .
F2A F 1.15955(11) 0.30237(9) 0.15257(10) 0.0375(3) Uani 1 1 d . . . . .
B1 B 0.4704(2) 0.24054(18) 0.68999(17) 0.0259(5) Uani 1 1 d . . . . .
B2 B 0.5974(2) 0.4111(2) 1.31194(18) 0.0316(5) Uani 1 1 d . . . . .
B1A B 1.1364(2) 0.20095(19) 0.22223(18) 0.0310(5) Uani 1 1 d . . . . .
N1 N 0.59160(15) 0.22712(12) 0.71780(11) 0.0236(3) Uani 1 1 d . . . . .
N2 N 0.60155(14) 0.24546(12) 0.79131(11) 0.0236(3) Uani 1 1 d . . . . .
N3 N 0.36519(15) 0.25615(12) 0.78056(12) 0.0240(3) Uani 1 1 d . . . . .
N4 N 0.38319(15) 0.27458(12) 0.85166(12) 0.0240(3) Uani 1 1 d . . . . .
N5 N 0.47566(15) 0.43940(12) 1.28368(12) 0.0253(3) Uani 1 1 d . . . . .
N6 N 0.46384(15) 0.41699(12) 1.21249(11) 0.0240(3) Uani 1 1 d . . . . .
N7 N 0.69984(15) 0.43354(12) 1.20652(12) 0.0266(4) Uani 1 1 d . . . . .
N8 N 0.68324(15) 0.41506(12) 1.13501(12) 0.0258(4) Uani 1 1 d . . . . .
N1A N 1.10606(15) 0.13468(12) 0.17359(12) 0.0282(4) Uani 1 1 d . . . . .
N2A N 1.19302(16) 0.09172(12) 0.12016(12) 0.0286(4) Uani 1 1 d . . . . .
N3A N 1.25614(16) 0.15019(13) 0.24734(12) 0.0286(4) Uani 1 1 d . . . . .
N4A N 1.33754(16) 0.10422(12) 0.19470(12) 0.0282(4) Uani 1 1 d . . . . .
C1 C 0.49937(17) 0.27322(14) 0.85231(14) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.70218(17) 0.19284(14) 0.65991(14) 0.0239(4) Uani 1 1 d . . . . .
C3 C 0.7163(2) 0.20575(17) 0.56147(16) 0.0313(4) Uani 1 1 d . . . . .
H3 H 0.650(2) 0.2350(17) 0.5331(16) 0.028(5) Uiso 1 1 d . . . . .
C4 C 0.8244(2) 0.17457(18) 0.50465(17) 0.0356(5) Uani 1 1 d . . . . .
H4 H 0.835(2) 0.1803(19) 0.441(2) 0.043(7) Uiso 1 1 d . . . . .
C5 C 0.9186(2) 0.13117(17) 0.54504(17) 0.0339(5) Uani 1 1 d . . . . .
H5 H 0.991(3) 0.109(2) 0.510(2) 0.048(7) Uiso 1 1 d . . . . .
C6 C 0.90400(19) 0.11862(16) 0.64311(16) 0.0307(4) Uani 1 1 d . . . . .
H6 H 0.970(2) 0.0895(19) 0.6728(19) 0.042(6) Uiso 1 1 d . . . . .
C7 C 0.79672(18) 0.14888(15) 0.70084(16) 0.0274(4) Uani 1 1 d . . . . .
H7 H 0.7861(19) 0.1358(16) 0.7681(17) 0.024(5) Uiso 1 1 d . . . . .
C8 C 0.23796(17) 0.24838(14) 0.79113(15) 0.0247(4) Uani 1 1 d . . . . .
C9 C 0.2073(2) 0.27069(16) 0.70415(16) 0.0291(4) Uani 1 1 d . . . . .
H9 H 0.271(2) 0.2926(19) 0.641(2) 0.040(6) Uiso 1 1 d . . . . .
C10 C 0.08528(19) 0.26100(16) 0.71385(17) 0.0311(5) Uani 1 1 d . . . . .
H10 H 0.066(2) 0.2787(17) 0.6537(19) 0.035(6) Uiso 1 1 d . . . . .
C11 C -0.0067(2) 0.22886(16) 0.80926(17) 0.0324(5) Uani 1 1 d . . . . .
H11 H -0.089(2) 0.2213(17) 0.8161(17) 0.033(6) Uiso 1 1 d . . . . .
C12 C 0.0238(2) 0.20602(17) 0.89589(17) 0.0335(5) Uani 1 1 d . . . . .
H12 H -0.041(2) 0.1840(17) 0.9645(19) 0.033(6) Uiso 1 1 d . . . . .
C13 C 0.14630(19) 0.21633(16) 0.88695(16) 0.0295(4) Uani 1 1 d . . . . .
H13 H 0.1663(19) 0.1982(16) 0.9471(17) 0.027(5) Uiso 1 1 d . . . . .
C14 C 0.51661(18) 0.30067(14) 0.93010(14) 0.0233(4) Uani 1 1 d . . . . .
C15 C 0.62962(18) 0.28739(15) 0.94820(15) 0.0264(4) Uani 1 1 d . . . . .
H15 H 0.698(2) 0.2560(17) 0.9113(16) 0.026(5) Uiso 1 1 d . . . . .
C16 C 0.64470(18) 0.31601(15) 1.01930(15) 0.0271(4) Uani 1 1 d . . . . .
H16 H 0.721(2) 0.3026(18) 1.0347(18) 0.036(6) Uiso 1 1 d . . . . .
C17 C 0.54771(18) 0.36040(14) 1.07481(14) 0.0238(4) Uani 1 1 d . . . . .
C18 C 0.43426(18) 0.37207(15) 1.05825(15) 0.0260(4) Uani 1 1 d . . . . .
H18 H 0.366(2) 0.4012(17) 1.0971(17) 0.030(6) Uiso 1 1 d . . . . .
C19 C 0.41912(18) 0.34270(15) 0.98737(15) 0.0256(4) Uani 1 1 d . . . . .
H19 H 0.340(2) 0.3536(16) 0.9765(16) 0.027(5) Uiso 1 1 d . . . . .
C20 C 0.56579(17) 0.39480(14) 1.14786(14) 0.0241(4) Uani 1 1 d . . . . .
C21 C 0.36770(18) 0.48054(14) 1.33726(14) 0.0242(4) Uani 1 1 d . . . . .
C22 C 0.35718(19) 0.48103(16) 1.43028(15) 0.0292(4) Uani 1 1 d . . . . .
H22 H 0.418(2) 0.4536(19) 1.4601(19) 0.042(6) Uiso 1 1 d . . . . .
C23 C 0.2514(2) 0.51956(17) 1.48221(17) 0.0329(5) Uani 1 1 d . . . . .
H23 H 0.244(2) 0.5172(17) 1.5448(19) 0.030(6) Uiso 1 1 d . . . . .
C24 C 0.1562(2) 0.55751(16) 1.44217(17) 0.0324(5) Uani 1 1 d . . . . .
H24 H 0.083(2) 0.585(2) 1.480(2) 0.045(7) Uiso 1 1 d . . . . .
C25 C 0.1672(2) 0.55602(16) 1.34935(16) 0.0325(5) Uani 1 1 d . . . . .
H25 H 0.102(2) 0.5838(19) 1.3184(19) 0.043(7) Uiso 1 1 d . . . . .
C26 C 0.27197(18) 0.51811(15) 1.29647(15) 0.0274(4) Uani 1 1 d . . . . .
H26 H 0.279(2) 0.5191(16) 1.2308(17) 0.028(5) Uiso 1 1 d . . . . .
C27 C 0.82128(18) 0.47042(15) 1.18451(16) 0.0288(4) Uani 1 1 d . . . . .
C28 C 0.8717(2) 0.43237(17) 1.26307(17) 0.0312(5) Uani 1 1 d . . . . .
H28 H 0.822(3) 0.382(2) 1.333(2) 0.050(7) Uiso 1 1 d . . . . .
C29 C 0.9904(2) 0.46408(18) 1.24295(18) 0.0354(5) Uani 1 1 d . . . . .
H29 H 1.029(3) 0.435(2) 1.296(2) 0.058(8) Uiso 1 1 d . . . . .
C30 C 1.0572(2) 0.53320(18) 1.14704(19) 0.0380(5) Uani 1 1 d . . . . .
H30 H 1.142(3) 0.557(2) 1.134(2) 0.049(7) Uiso 1 1 d . . . . .
C31 C 1.0061(2) 0.57175(18) 1.06905(19) 0.0377(5) Uani 1 1 d . . . . .
H31 H 1.055(3) 0.618(2) 1.000(2) 0.057(8) Uiso 1 1 d . . . . .
C32 C 0.8876(2) 0.54000(16) 1.08732(17) 0.0328(5) Uani 1 1 d . . . . .
H32 H 0.856(2) 0.5628(17) 1.0321(18) 0.033(6) Uiso 1 1 d . . . . .
C1A C 1.30801(19) 0.08710(14) 0.12487(14) 0.0272(4) Uani 1 1 d . . . . .
C2A C 0.98148(19) 0.11691(15) 0.18299(15) 0.0298(4) Uani 1 1 d . . . . .
C3A C 0.8870(2) 0.18074(16) 0.21206(16) 0.0343(5) Uani 1 1 d . . . . .
H3A H 0.903(2) 0.2399(17) 0.2216(16) 0.028(5) Uiso 1 1 d . . . . .
C4A C 0.7654(2) 0.15906(18) 0.22828(18) 0.0397(5) Uani 1 1 d . . . . .
H4A H 0.698(3) 0.202(2) 0.251(2) 0.047(7) Uiso 1 1 d . . . . .
C5A C 0.7371(2) 0.07634(18) 0.21311(19) 0.0412(5) Uani 1 1 d . . . . .
H5A H 0.652(3) 0.060(2) 0.231(2) 0.048(7) Uiso 1 1 d . . . . .
C6A C 0.8318(2) 0.01584(18) 0.18036(19) 0.0400(5) Uani 1 1 d . . . . .
H6A H 0.814(2) -0.040(2) 0.1702(19) 0.041(6) Uiso 1 1 d . . . . .
C7A C 0.9536(2) 0.03476(17) 0.16588(17) 0.0343(5) Uani 1 1 d . . . . .
H7A H 1.019(2) -0.0096(19) 0.1427(18) 0.037(6) Uiso 1 1 d . . . . .
C8A C 1.2801(2) 0.14652(16) 0.33431(15) 0.0317(5) Uani 1 1 d . . . . .
C9A C 1.2438(2) 0.22805(17) 0.36516(16) 0.0340(5) Uani 1 1 d . . . . .
H9A H 1.207(2) 0.290(2) 0.325(2) 0.045(7) Uiso 1 1 d . . . . .
C10A C 1.2628(2) 0.22232(19) 0.45180(17) 0.0411(5) Uani 1 1 d . . . . .
H10A H 1.237(2) 0.278(2) 0.473(2) 0.047(7) Uiso 1 1 d . . . . .
C11A C 1.3159(3) 0.1356(2) 0.5079(2) 0.0558(7) Uani 1 1 d . . . . .
H11A H 1.329(3) 0.130(2) 0.567(3) 0.069(9) Uiso 1 1 d . . . . .
C12A C 1.3517(3) 0.0542(2) 0.4765(2) 0.0633(8) Uani 1 1 d . . . . .
H12A H 1.384(3) -0.009(3) 0.518(3) 0.087(11) Uiso 1 1 d . . . . .
C13A C 1.3354(3) 0.0598(2) 0.38923(19) 0.0476(6) Uani 1 1 d . . . . .
H13A H 1.367(3) 0.006(2) 0.364(2) 0.062(8) Uiso 1 1 d . . . . .
C14A C 1.40590(19) 0.04253(14) 0.06069(14) 0.0272(4) Uani 1 1 d . . . . .
C15A C 1.3831(2) 0.01463(16) -0.00930(16) 0.0303(4) Uani 1 1 d . . . . .
H15A H 1.305(2) 0.0254(17) -0.0151(17) 0.030(6) Uiso 1 1 d . . . . .
C16A C 1.4752(2) -0.02727(16) -0.06848(15) 0.0304(5) Uani 1 1 d . . . . .
H16A H 1.460(2) -0.0426(17) -0.1178(18) 0.031(6) Uiso 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
F1 B1 1.375(3) . ?
F2 B1 1.378(3) . ?
F3 B2 1.376(3) . ?
F4 B2 1.367(3) . ?
F1A B1A 1.362(3) . ?
F2A B1A 1.370(3) . ?
B1 N3 1.556(3) . ?
B1 N1 1.562(3) . ?
B2 N7 1.546(3) . ?
B2 N5 1.563(3) . ?
B1A N1A 1.551(3) . ?
B1A N3A 1.565(3) . ?
N1 N2 1.297(2) . ?
N1 C2 1.427(3) . ?
N2 C1 1.346(3) . ?
N3 N4 1.303(2) . ?
N3 C8 1.426(2) . ?
N4 C1 1.336(2) . ?
N5 N6 1.305(2) . ?
N5 C21 1.429(3) . ?
N6 C20 1.337(3) . ?
N7 N8 1.302(2) . ?
N7 C27 1.427(3) . ?
N8 C20 1.344(2) . ?
N1A N2A 1.310(2) . ?
N1A C2A 1.431(3) . ?
N2A C1A 1.341(3) . ?
N3A N4A 1.302(2) . ?
N3A C8A 1.427(3) . ?
N4A C1A 1.343(3) . ?
C1 C14 1.474(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.394(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.97(2) . ?
C4 C5 1.385(3) . ?
C4 H4 0.91(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.91(3) . ?
C6 C7 1.375(3) . ?
C6 H6 0.98(3) . ?
C7 H7 0.93(2) . ?
C8 C13 1.386(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.375(3) . ?
C9 H9 0.93(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.95(2) . ?
C11 C12 1.384(3) . ?
C11 H11 0.93(2) . ?
C12 C13 1.386(3) . ?
C12 H12 0.99(2) . ?
C13 H13 0.95(2) . ?
C14 C19 1.394(3) . ?
C14 C15 1.396(3) . ?
C15 C16 1.375(3) . ?
C15 H15 0.97(2) . ?
C16 C17 1.397(3) . ?
C16 H16 0.96(2) . ?
C17 C18 1.391(3) . ?
C17 C20 1.473(3) . ?
C18 C19 1.379(3) . ?
C18 H18 0.96(2) . ?
C19 H19 0.96(2) . ?
C21 C22 1.383(3) . ?
C21 C26 1.393(3) . ?
C22 C23 1.383(3) . ?
C22 H22 0.93(3) . ?
C23 C24 1.381(3) . ?
C23 H23 0.91(2) . ?
C24 C25 1.385(3) . ?
C24 H24 0.98(3) . ?
C25 C26 1.378(3) . ?
C25 H25 0.98(3) . ?
C26 H26 0.97(2) . ?
C27 C32 1.382(3) . ?
C27 C28 1.391(3) . ?
C28 C29 1.378(3) . ?
C28 H28 1.01(3) . ?
C29 C30 1.370(3) . ?
C29 H29 0.98(3) . ?
C30 C31 1.388(3) . ?
C30 H30 0.99(3) . ?
C31 C32 1.384(3) . ?
C31 H31 0.97(3) . ?
C32 H32 0.95(2) . ?
C1A C14A 1.476(3) . ?
C2A C7A 1.391(3) . ?
C2A C3A 1.392(3) . ?
C3A C4A 1.381(3) . ?
C3A H3A 0.96(2) . ?
C4A C5A 1.382(3) . ?
C4A H4A 0.98(3) . ?
C5A C6A 1.380(4) . ?
C5A H5A 0.95(3) . ?
C6A C7A 1.380(3) . ?
C6A H6A 0.92(3) . ?
C7A H7A 0.98(3) . ?
C8A C9A 1.387(3) . ?
C8A C13A 1.389(3) . ?
C9A C10A 1.382(3) . ?
C9A H9A 0.98(3) . ?
C10A C11A 1.382(4) . ?
C10A H10A 0.95(3) . ?
C11A C12A 1.389(4) . ?
C11A H11A 0.93(3) . ?
C12A C13A 1.378(4) . ?
C12A H12A 0.97(4) . ?
C13A H13A 0.97(3) . ?
C14A C15A 1.394(3) . ?
C14A C16A 1.395(3) 2_855 ?
C15A C16A 1.378(3) . ?
C15A H15A 0.92(2) . ?
C16A C14A 1.395(3) 2_855 ?
C16A H16A 0.94(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
F1 B1 F2 111.59(16) . . ?
F1 B1 N3 109.73(16) . . ?
F2 B1 N3 110.10(17) . . ?
F1 B1 N1 109.92(16) . . ?
F2 B1 N1 110.01(16) . . ?
N3 B1 N1 105.30(15) . . ?
F4 B2 F3 113.06(18) . . ?
F4 B2 N7 109.53(18) . . ?
F3 B2 N7 110.03(18) . . ?
F4 B2 N5 111.78(18) . . ?
F3 B2 N5 109.23(18) . . ?
N7 B2 N5 102.71(15) . . ?
F1A B1A F2A 111.83(19) . . ?
F1A B1A N1A 111.49(17) . . ?
F2A B1A N1A 109.67(17) . . ?
F1A B1A N3A 108.94(17) . . ?
F2A B1A N3A 111.30(17) . . ?
N1A B1A N3A 103.32(17) . . ?
N2 N1 C2 115.29(14) . . ?
N2 N1 B1 124.87(16) . . ?
C2 N1 B1 119.84(15) . . ?
N1 N2 C1 118.56(15) . . ?
N4 N3 C8 115.24(15) . . ?
N4 N3 B1 124.85(15) . . ?
C8 N3 B1 119.89(15) . . ?
N3 N4 C1 118.61(16) . . ?
N6 N5 C21 115.36(15) . . ?
N6 N5 B2 119.87(16) . . ?
C21 N5 B2 124.50(15) . . ?
N5 N6 C20 118.74(15) . . ?
N8 N7 C27 116.09(16) . . ?
N8 N7 B2 122.53(16) . . ?
C27 N7 B2 121.28(16) . . ?
N7 N8 C20 116.89(16) . . ?
N2A N1A C2A 115.27(16) . . ?
N2A N1A B1A 122.22(16) . . ?
C2A N1A B1A 122.51(17) . . ?
N1A N2A C1A 118.50(16) . . ?
N4A N3A C8A 115.01(16) . . ?
N4A N3A B1A 123.39(16) . . ?
C8A N3A B1A 121.53(17) . . ?
N3A N4A C1A 117.62(17) . . ?
N4 C1 N2 126.29(17) . . ?
N4 C1 C14 116.89(17) . . ?
N2 C1 C14 116.77(16) . . ?
C3 C2 C7 120.03(18) . . ?
C3 C2 N1 119.47(17) . . ?
C7 C2 N1 120.49(17) . . ?
C4 C3 C2 119.50(19) . . ?
C4 C3 H3 120.1(13) . . ?
C2 C3 H3 120.4(13) . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 121.3(16) . . ?
C5 C4 H4 118.1(16) . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 117.7(17) . . ?
C4 C5 H5 122.6(17) . . ?
C7 C6 C5 120.47(19) . . ?
C7 C6 H6 118.4(15) . . ?
C5 C6 H6 121.2(15) . . ?
C6 C7 C2 119.78(19) . . ?
C6 C7 H7 119.4(13) . . ?
C2 C7 H7 120.7(13) . . ?
C13 C8 C9 120.27(18) . . ?
C13 C8 N3 120.58(17) . . ?
C9 C8 N3 119.12(18) . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 122.0(15) . . ?
C8 C9 H9 118.4(15) . . ?
C9 C10 C11 120.52(19) . . ?
C9 C10 H10 118.3(14) . . ?
C11 C10 H10 121.1(14) . . ?
C10 C11 C12 119.98(19) . . ?
C10 C11 H11 120.6(14) . . ?
C12 C11 H11 119.4(14) . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.8(13) . . ?
C13 C12 H12 119.2(13) . . ?
C8 C13 C12 119.66(19) . . ?
C8 C13 H13 121.2(13) . . ?
C12 C13 H13 119.1(13) . . ?
C19 C14 C15 117.80(17) . . ?
C19 C14 C1 120.19(16) . . ?
C15 C14 C1 122.01(18) . . ?
C16 C15 C14 121.07(19) . . ?
C16 C15 H15 119.4(13) . . ?
C14 C15 H15 119.5(13) . . ?
C15 C16 C17 120.98(18) . . ?
C15 C16 H16 120.7(14) . . ?
C17 C16 H16 118.2(14) . . ?
C18 C17 C16 118.09(17) . . ?
C18 C17 C20 121.09(18) . . ?
C16 C17 C20 120.82(16) . . ?
C19 C18 C17 120.81(19) . . ?
C19 C18 H18 120.3(13) . . ?
C17 C18 H18 118.9(13) . . ?
C18 C19 C14 121.23(18) . . ?
C18 C19 H19 118.6(13) . . ?
C14 C19 H19 120.2(13) . . ?
N6 C20 N8 124.78(17) . . ?
N6 C20 C17 117.24(16) . . ?
N8 C20 C17 117.31(17) . . ?
C22 C21 C26 120.17(19) . . ?
C22 C21 N5 120.11(17) . . ?
C26 C21 N5 119.71(17) . . ?
C21 C22 C23 119.59(19) . . ?
C21 C22 H22 121.4(16) . . ?
C23 C22 H22 119.0(15) . . ?
C24 C23 C22 120.7(2) . . ?
C24 C23 H23 120.3(14) . . ?
C22 C23 H23 119.0(14) . . ?
C23 C24 C25 119.3(2) . . ?
C23 C24 H24 119.1(15) . . ?
C25 C24 H24 121.6(15) . . ?
C26 C25 C24 120.79(19) . . ?
C26 C25 H25 118.1(15) . . ?
C24 C25 H25 121.0(15) . . ?
C25 C26 C21 119.44(18) . . ?
C25 C26 H26 119.6(13) . . ?
C21 C26 H26 120.9(13) . . ?
C32 C27 C28 121.15(19) . . ?
C32 C27 N7 120.80(18) . . ?
C28 C27 N7 118.03(19) . . ?
C29 C28 C27 119.2(2) . . ?
C29 C28 H28 120.8(15) . . ?
C27 C28 H28 120.0(15) . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 H29 119.2(17) . . ?
C28 C29 H29 120.4(17) . . ?
C29 C30 C31 120.3(2) . . ?
C29 C30 H30 119.5(15) . . ?
C31 C30 H30 120.2(15) . . ?
C32 C31 C30 120.3(2) . . ?
C32 C31 H31 119.3(17) . . ?
C30 C31 H31 120.3(17) . . ?
C27 C32 C31 118.7(2) . . ?
C27 C32 H32 121.7(14) . . ?
C31 C32 H32 119.4(14) . . ?
N2A C1A N4A 125.07(19) . . ?
N2A C1A C14A 117.67(17) . . ?
N4A C1A C14A 116.38(17) . . ?
C7A C2A C3A 119.78(19) . . ?
C7A C2A N1A 120.49(19) . . ?
C3A C2A N1A 119.71(18) . . ?
C4A C3A C2A 119.7(2) . . ?
C4A C3A H3A 118.1(13) . . ?
C2A C3A H3A 122.2(13) . . ?
C3A C4A C5A 120.6(2) . . ?
C3A C4A H4A 120.2(15) . . ?
C5A C4A H4A 119.2(15) . . ?
C6A C5A C4A 119.4(2) . . ?
C6A C5A H5A 122.5(16) . . ?
C4A C5A H5A 117.9(16) . . ?
C5A C6A C7A 120.9(2) . . ?
C5A C6A H6A 120.2(16) . . ?
C7A C6A H6A 118.9(16) . . ?
C6A C7A C2A 119.5(2) . . ?
C6A C7A H7A 119.1(14) . . ?
C2A C7A H7A 121.3(14) . . ?
C9A C8A C13A 120.7(2) . . ?
C9A C8A N3A 119.51(19) . . ?
C13A C8A N3A 119.70(19) . . ?
C10A C9A C8A 119.3(2) . . ?
C10A C9A H9A 120.8(15) . . ?
C8A C9A H9A 119.8(15) . . ?
C11A C10A C9A 120.3(2) . . ?
C11A C10A H10A 120.3(16) . . ?
C9A C10A H10A 119.4(16) . . ?
C10A C11A C12A 119.9(2) . . ?
C10A C11A H11A 122(2) . . ?
C12A C11A H11A 118(2) . . ?
C13A C12A C11A 120.3(3) . . ?
C13A C12A H12A 119(2) . . ?
C11A C12A H12A 121(2) . . ?
C12A C13A C8A 119.3(2) . . ?
C12A C13A H13A 120.6(18) . . ?
C8A C13A H13A 120.0(18) . . ?
C15A C14A C16A 118.0(2) . 2_855 ?
C15A C14A C1A 121.45(18) . . ?
C16A C14A C1A 120.54(17) 2_855 . ?
C16A C15A C14A 120.9(2) . . ?
C16A C15A H15A 121.0(14) . . ?
C14A C15A H15A 118.1(14) . . ?
C15A C16A C14A 121.13(19) . 2_855 ?
C15A C16A H16A 120.3(14) . . ?
C14A C16A H16A 118.4(14) 2_855 . ?

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
F1 B1 N1 N2 -129.62(18) . . . . ?
F2 B1 N1 N2 107.11(19) . . . . ?
N3 B1 N1 N2 -11.5(2) . . . . ?
F1 B1 N1 C2 50.7(2) . . . . ?
F2 B1 N1 C2 -72.5(2) . . . . ?
N3 B1 N1 C2 168.86(15) . . . . ?
C2 N1 N2 C1 -176.84(15) . . . . ?
B1 N1 N2 C1 3.5(3) . . . . ?
F1 B1 N3 N4 130.46(17) . . . . ?
F2 B1 N3 N4 -106.34(19) . . . . ?
N1 B1 N3 N4 12.2(2) . . . . ?
F1 B1 N3 C8 -48.2(2) . . . . ?
F2 B1 N3 C8 75.0(2) . . . . ?
N1 B1 N3 C8 -166.44(15) . . . . ?
C8 N3 N4 C1 173.83(15) . . . . ?
B1 N3 N4 C1 -4.9(3) . . . . ?
F4 B2 N5 N6 155.30(17) . . . . ?
F3 B2 N5 N6 -78.8(2) . . . . ?
N7 B2 N5 N6 38.0(2) . . . . ?
F4 B2 N5 C21 -30.9(3) . . . . ?
F3 B2 N5 C21 95.0(2) . . . . ?
N7 B2 N5 C21 -148.22(16) . . . . ?
C21 N5 N6 C20 168.99(16) . . . . ?
B2 N5 N6 C20 -16.7(2) . . . . ?
F4 B2 N7 N8 -155.42(17) . . . . ?
F3 B2 N7 N8 79.7(2) . . . . ?
N5 B2 N7 N8 -36.5(2) . . . . ?
F4 B2 N7 C27 28.2(3) . . . . ?
F3 B2 N7 C27 -96.6(2) . . . . ?
N5 B2 N7 C27 147.17(17) . . . . ?
C27 N7 N8 C20 -170.72(16) . . . . ?
B2 N7 N8 C20 12.8(3) . . . . ?
F1A B1A N1A N2A -148.25(18) . . . . ?
F2A B1A N1A N2A 87.3(2) . . . . ?
N3A B1A N1A N2A -31.4(2) . . . . ?
F1A B1A N1A C2A 32.3(3) . . . . ?
F2A B1A N1A C2A -92.1(2) . . . . ?
N3A B1A N1A C2A 149.19(16) . . . . ?
C2A N1A N2A C1A -166.91(16) . . . . ?
B1A N1A N2A C1A 13.7(3) . . . . ?
F1A B1A N3A N4A 148.23(17) . . . . ?
F2A B1A N3A N4A -88.0(2) . . . . ?
N1A B1A N3A N4A 29.6(2) . . . . ?
F1A B1A N3A C8A -28.4(3) . . . . ?
F2A B1A N3A C8A 95.4(2) . . . . ?
N1A B1A N3A C8A -147.00(16) . . . . ?
C8A N3A N4A C1A 167.22(16) . . . . ?
B1A N3A N4A C1A -9.6(3) . . . . ?
N3 N4 C1 N2 -6.2(3) . . . . ?
N3 N4 C1 C14 176.41(15) . . . . ?
N1 N2 C1 N4 6.9(3) . . . . ?
N1 N2 C1 C14 -175.73(15) . . . . ?
N2 N1 C2 C3 -157.53(17) . . . . ?
B1 N1 C2 C3 22.2(2) . . . . ?
N2 N1 C2 C7 21.0(2) . . . . ?
B1 N1 C2 C7 -159.34(17) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
N1 C2 C3 C4 178.67(18) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
N1 C2 C7 C6 -178.38(17) . . . . ?
N4 N3 C8 C13 -27.4(2) . . . . ?
B1 N3 C8 C13 151.35(18) . . . . ?
N4 N3 C8 C9 154.33(17) . . . . ?
B1 N3 C8 C9 -26.9(3) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
N3 C8 C9 C10 178.44(18) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
N3 C8 C13 C12 -177.89(18) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
N4 C1 C14 C19 -10.5(3) . . . . ?
N2 C1 C14 C19 171.90(16) . . . . ?
N4 C1 C14 C15 170.44(17) . . . . ?
N2 C1 C14 C15 -7.2(3) . . . . ?
C19 C14 C15 C16 -0.8(3) . . . . ?
C1 C14 C15 C16 178.30(18) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C18 1.8(3) . . . . ?
C15 C16 C17 C20 -177.53(18) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C20 C17 C18 C19 177.95(17) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C15 C14 C19 C18 1.2(3) . . . . ?
C1 C14 C19 C18 -177.90(17) . . . . ?
N5 N6 C20 N8 -15.2(3) . . . . ?
N5 N6 C20 C17 174.44(15) . . . . ?
N7 N8 C20 N6 17.5(3) . . . . ?
N7 N8 C20 C17 -172.20(15) . . . . ?
C18 C17 C20 N6 13.6(3) . . . . ?
C16 C17 C20 N6 -167.04(17) . . . . ?
C18 C17 C20 N8 -157.45(17) . . . . ?
C16 C17 C20 N8 21.9(3) . . . . ?
N6 N5 C21 C22 162.74(17) . . . . ?
B2 N5 C21 C22 -11.3(3) . . . . ?
N6 N5 C21 C26 -15.9(2) . . . . ?
B2 N5 C21 C26 170.03(18) . . . . ?
C26 C21 C22 C23 -0.4(3) . . . . ?
N5 C21 C22 C23 -179.00(18) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C21 0.2(3) . . . . ?
C22 C21 C26 C25 0.2(3) . . . . ?
N5 C21 C26 C25 178.88(17) . . . . ?
N8 N7 C27 C32 38.5(3) . . . . ?
B2 N7 C27 C32 -144.9(2) . . . . ?
N8 N7 C27 C28 -139.99(18) . . . . ?
B2 N7 C27 C28 36.6(3) . . . . ?
C32 C27 C28 C29 -0.6(3) . . . . ?
N7 C27 C28 C29 177.86(18) . . . . ?
C27 C28 C29 C30 0.8(3) . . . . ?
C28 C29 C30 C31 -0.2(3) . . . . ?
C29 C30 C31 C32 -0.5(3) . . . . ?
C28 C27 C32 C31 -0.1(3) . . . . ?
N7 C27 C32 C31 -178.55(19) . . . . ?
C30 C31 C32 C27 0.7(3) . . . . ?
N1A N2A C1A N4A 13.7(3) . . . . ?
N1A N2A C1A C14A -177.42(16) . . . . ?
N3A N4A C1A N2A -15.8(3) . . . . ?
N3A N4A C1A C14A 175.28(16) . . . . ?
N2A N1A C2A C7A 19.6(3) . . . . ?
B1A N1A C2A C7A -160.96(19) . . . . ?
N2A N1A C2A C3A -162.06(17) . . . . ?
B1A N1A C2A C3A 17.4(3) . . . . ?
C7A C2A C3A C4A 3.0(3) . . . . ?
N1A C2A C3A C4A -175.37(18) . . . . ?
C2A C3A C4A C5A -1.8(3) . . . . ?
C3A C4A C5A C6A -0.7(3) . . . . ?
C4A C5A C6A C7A 2.2(4) . . . . ?
C5A C6A C7A C2A -1.0(3) . . . . ?
C3A C2A C7A C6A -1.6(3) . . . . ?
N1A C2A C7A C6A 176.77(19) . . . . ?
N4A N3A C8A C9A 148.59(19) . . . . ?
B1A N3A C8A C9A -34.5(3) . . . . ?
N4A N3A C8A C13A -33.7(3) . . . . ?
B1A N3A C8A C13A 143.2(2) . . . . ?
C13A C8A C9A C10A -0.2(3) . . . . ?
N3A C8A C9A C10A 177.48(19) . . . . ?
C8A C9A C10A C11A -0.8(3) . . . . ?
C9A C10A C11A C12A 0.7(4) . . . . ?
C10A C11A C12A C13A 0.6(5) . . . . ?
C11A C12A C13A C8A -1.6(5) . . . . ?
C9A C8A C13A C12A 1.4(4) . . . . ?
N3A C8A C13A C12A -176.3(2) . . . . ?
N2A C1A C14A C15A 5.6(3) . . . . ?
N4A C1A C14A C15A 175.42(17) . . . . ?
N2A C1A C14A C16A -174.50(17) . . . 2_855 ?
N4A C1A C14A C16A -4.7(3) . . . 2_855 ?
C16A C14A C15A C16A 0.3(3) 2_855 . . . ?
C1A C14A C15A C16A -179.75(18) . . . . ?
C14A C15A C16A C14A -0.4(3) . . . 2_855 ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.046

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
####################################################################### 
# 
# 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_b15155
_database_code_depnum_ccdc_archive 'CCDC 1401467'
_audit_update_record             
;
2015-05-15 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 B2 F4 N8'
_chemical_formula_weight         618.21
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.424(7)
_cell_length_b                   17.935(7)
_cell_length_c                   18.574(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.646(10)
_cell_angle_gamma                90
_cell_volume                     5743(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    110
_cell_measurement_reflns_used    7296
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.59
_exptl_crystal_description       Plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             2544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52269
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.344
_diffrn_reflns_theta_max         28.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7169
_reflns_number_gt                4497
_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
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_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)+(0.0446P)²+1.6682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7169
_refine_ls_number_parameters     511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
N1 N 0.40050(8) 0.70780(8) 0.41386(8) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.38064(8) 0.71188(8) 0.47447(8) 0.0207(3) Uani 1 1 d . . . . .
N3 N 0.39525(8) 0.57066(8) 0.41997(8) 0.0202(3) Uani 1 1 d . . . . .
N4 N 0.37298(8) 0.57890(8) 0.47901(8) 0.0210(3) Uani 1 1 d . . . . .
C1 C 0.36200(9) 0.64780(9) 0.50107(9) 0.0201(4) Uani 1 1 d . . . . .
B1 B 0.39533(12) 0.63594(11) 0.36510(11) 0.0223(4) Uani 1 1 d . . . . .
F1 F 0.45880(6) 0.63250(6) 0.34286(6) 0.0321(3) Uani 1 1 d . . . . .
F2 F 0.32676(6) 0.63480(6) 0.30280(5) 0.0317(3) Uani 1 1 d . . . . .
C2 C 0.42644(9) 0.77711(9) 0.39282(9) 0.0190(4) Uani 1 1 d . . . . .
C3 C 0.41053(10) 0.79190(10) 0.31496(10) 0.0219(4) Uani 1 1 d . . . . .
H3 H 0.3839(10) 0.7560(10) 0.2769(10) 0.022(5) Uiso 1 1 d . . . . .
C4 C 0.43281(10) 0.85971(10) 0.29427(10) 0.0233(4) Uani 1 1 d . . . . .
H4 H 0.4215(10) 0.8711(10) 0.2416(11) 0.032(5) Uiso 1 1 d . . . . .
C5 C 0.47083(10) 0.91166(10) 0.34919(10) 0.0250(4) Uani 1 1 d . . . . .
H5 H 0.4856(10) 0.9589(10) 0.3326(10) 0.025(5) Uiso 1 1 d . . . . .
C6 C 0.48732(11) 0.89623(10) 0.42656(11) 0.0250(4) Uani 1 1 d . . . . .
H6 H 0.5147(10) 0.9308(10) 0.4650(10) 0.021(5) Uiso 1 1 d . . . . .
C7 C 0.46526(10) 0.82866(10) 0.44875(10) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.4742(9) 0.8153(9) 0.4987(10) 0.018(4) Uiso 1 1 d . . . . .
C8 C 0.41268(9) 0.49503(9) 0.40659(10) 0.0212(4) Uani 1 1 d . . . . .
C9 C 0.41898(10) 0.47603(11) 0.33620(10) 0.0257(4) Uani 1 1 d . . . . .
H9 H 0.4103(10) 0.5146(10) 0.2966(10) 0.024(5) Uiso 1 1 d . . . . .
C10 C 0.43445(11) 0.40272(11) 0.32289(11) 0.0301(4) Uani 1 1 d . . . . .
H10 H 0.4381(10) 0.3892(10) 0.2742(11) 0.029(5) Uiso 1 1 d . . . . .
C11 C 0.44310(11) 0.34869(11) 0.37821(11) 0.0295(4) Uani 1 1 d . . . . .
H11 H 0.4549(11) 0.2983(12) 0.3690(12) 0.042(6) Uiso 1 1 d . . . . .
C12 C 0.43618(10) 0.36762(11) 0.44756(11) 0.0270(4) Uani 1 1 d . . . . .
H12 H 0.4418(11) 0.3296(11) 0.4875(11) 0.039(6) Uiso 1 1 d . . . . .
C13 C 0.42121(10) 0.44047(10) 0.46240(10) 0.0239(4) Uani 1 1 d . . . . .
H13 H 0.4163(9) 0.4520(9) 0.5115(10) 0.021(4) Uiso 1 1 d . . . . .
C14 C 0.33056(10) 0.65304(9) 0.56396(9) 0.0207(4) Uani 1 1 d . . . . .
C15 C 0.30669(10) 0.58788(10) 0.58954(10) 0.0213(4) Uani 1 1 d . . . . .
H15 H 0.3112(10) 0.5399(10) 0.5669(10) 0.025(5) Uiso 1 1 d . . . . .
C16 C 0.27326(9) 0.58952(9) 0.64610(9) 0.0195(4) Uani 1 1 d . . . . .
C17 C 0.26590(10) 0.65771(10) 0.67887(10) 0.0227(4) Uani 1 1 d . . . . .
H17 H 0.2451(10) 0.6608(9) 0.7206(10) 0.027(5) Uiso 1 1 d . . . . .
C18 C 0.29041(10) 0.72241(11) 0.65404(10) 0.0251(4) Uani 1 1 d . . . . .
H18 H 0.2848(11) 0.7685(11) 0.6751(11) 0.031(5) Uiso 1 1 d . . . . .
C19 C 0.32158(10) 0.72097(10) 0.59617(10) 0.0239(4) Uani 1 1 d . . . . .
H19 H 0.3362(10) 0.7647(10) 0.5772(10) 0.027(5) Uiso 1 1 d . . . . .
N5 N 0.22861(8) 0.39434(8) 0.64384(7) 0.0190(3) Uani 1 1 d . . . . .
N6 N 0.26220(8) 0.45659(8) 0.63633(7) 0.0200(3) Uani 1 1 d . . . . .
N7 N 0.17824(8) 0.45862(8) 0.73098(7) 0.0191(3) Uani 1 1 d . . . . .
N8 N 0.21309(8) 0.51975(8) 0.72157(8) 0.0204(3) Uani 1 1 d . . . . .
C20 C 0.24451(9) 0.51884(9) 0.66665(9) 0.0191(4) Uani 1 1 d . . . . .
B2 B 0.15538(11) 0.39781(11) 0.66709(11) 0.0218(4) Uani 1 1 d . . . . .
F3 F 0.13987(6) 0.33072(6) 0.69285(6) 0.0321(3) Uani 1 1 d . . . . .
F4 F 0.09362(6) 0.42329(6) 0.60476(6) 0.0312(3) Uani 1 1 d . . . . .
C21 C 0.26471(10) 0.32846(9) 0.62847(9) 0.0193(4) Uani 1 1 d . . . . .
C22 C 0.22132(11) 0.26425(10) 0.60361(10) 0.0233(4) Uani 1 1 d . . . . .
H22 H 0.1684(11) 0.2644(9) 0.5975(10) 0.023(5) Uiso 1 1 d . . . . .
C23 C 0.25618(11) 0.20170(11) 0.58670(11) 0.0268(4) Uani 1 1 d . . . . .
H23 H 0.2267(11) 0.1583(11) 0.5697(11) 0.033(5) Uiso 1 1 d . . . . .
C24 C 0.33334(11) 0.20308(10) 0.59383(10) 0.0260(4) Uani 1 1 d . . . . .
H24 H 0.3580(10) 0.1590(10) 0.5812(10) 0.029(5) Uiso 1 1 d . . . . .
C25 C 0.37648(11) 0.26736(10) 0.61899(10) 0.0259(4) Uani 1 1 d . . . . .
H25 H 0.4295(12) 0.2682(11) 0.6253(11) 0.037(6) Uiso 1 1 d . . . . .
C26 C 0.34281(10) 0.33034(10) 0.63653(10) 0.0223(4) Uani 1 1 d . . . . .
H26 H 0.3729(10) 0.3756(10) 0.6551(10) 0.029(5) Uiso 1 1 d . . . . .
C27 C 0.16245(10) 0.45678(9) 0.80114(9) 0.0200(4) Uani 1 1 d . . . . .
C28 C 0.10375(10) 0.41139(10) 0.80713(11) 0.0247(4) Uani 1 1 d . . . . .
H28 H 0.0749(10) 0.3830(10) 0.7651(10) 0.028(5) Uiso 1 1 d . . . . .
C29 C 0.08820(11) 0.41124(11) 0.87499(11) 0.0283(4) Uani 1 1 d . . . . .
H29 H 0.0461(12) 0.3797(12) 0.8774(12) 0.046(6) Uiso 1 1 d . . . . .
C30 C 0.13067(11) 0.45550(11) 0.93625(11) 0.0287(4) Uani 1 1 d . . . . .
H30 H 0.1213(10) 0.4557(10) 0.9847(11) 0.030(5) Uiso 1 1 d . . . . .
C31 C 0.18858(11) 0.50121(11) 0.92965(10) 0.0267(4) Uani 1 1 d . . . . .
H31 H 0.2196(11) 0.5305(11) 0.9721(11) 0.035(5) Uiso 1 1 d . . . . .
C32 C 0.20502(10) 0.50183(10) 0.86252(10) 0.0227(4) Uani 1 1 d . . . . .
H32 H 0.2469(10) 0.5323(10) 0.8585(10) 0.025(5) Uiso 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
N1 N2 1.3026(18) . ?
N1 C2 1.435(2) . ?
N1 B1 1.559(2) . ?
N2 C1 1.343(2) . ?
N3 N4 1.3077(18) . ?
N3 C8 1.436(2) . ?
N3 B1 1.553(2) . ?
N4 C1 1.340(2) . ?
C1 C14 1.478(2) . ?
B1 F1 1.372(2) . ?
B1 F2 1.380(2) . ?
C2 C7 1.386(2) . ?
C2 C3 1.396(2) . ?
C3 C4 1.381(2) . ?
C3 H3 0.954(18) . ?
C4 C5 1.377(3) . ?
C4 H4 0.949(19) . ?
C5 C6 1.388(3) . ?
C5 H5 0.974(18) . ?
C6 C7 1.386(2) . ?
C6 H6 0.945(18) . ?
C7 H7 0.915(17) . ?
C8 C13 1.394(2) . ?
C8 C9 1.395(2) . ?
C9 C10 1.386(3) . ?
C9 H9 0.981(18) . ?
C10 C11 1.380(3) . ?
C10 H10 0.962(18) . ?
C11 C12 1.381(3) . ?
C11 H11 0.96(2) . ?
C12 C13 1.383(3) . ?
C12 H12 0.99(2) . ?
C13 H13 0.969(17) . ?
C14 C15 1.390(2) . ?
C14 C19 1.393(2) . ?
C15 C16 1.393(2) . ?
C15 H15 0.975(18) . ?
C16 C17 1.394(2) . ?
C16 C20 1.475(2) . ?
C17 C18 1.382(2) . ?
C17 H17 0.979(17) . ?
C18 C19 1.386(2) . ?
C18 H18 0.936(19) . ?
C19 H19 0.938(18) . ?
N5 N6 1.3078(19) . ?
N5 C21 1.433(2) . ?
N5 B2 1.556(2) . ?
N6 C20 1.341(2) . ?
N7 N8 1.3130(19) . ?
N7 C27 1.432(2) . ?
N7 B2 1.556(2) . ?
N8 C20 1.339(2) . ?
B2 F3 1.362(2) . ?
B2 F4 1.384(2) . ?
C21 C22 1.385(2) . ?
C21 C26 1.394(2) . ?
C22 C23 1.383(3) . ?
C22 H22 0.940(18) . ?
C23 C24 1.381(3) . ?
C23 H23 0.938(19) . ?
C24 C25 1.385(3) . ?
C24 H24 0.981(18) . ?
C25 C26 1.382(3) . ?
C25 H25 0.94(2) . ?
C26 H26 0.975(19) . ?
C27 C28 1.389(2) . ?
C27 C32 1.392(2) . ?
C28 C29 1.388(2) . ?
C28 H28 0.927(19) . ?
C29 C30 1.382(3) . ?
C29 H29 0.97(2) . ?
C30 C31 1.385(3) . ?
C30 H30 0.974(18) . ?
C31 C32 1.383(2) . ?
C31 H31 0.95(2) . ?
C32 H32 0.971(18) . ?

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 N1 C2 114.13(13) . . ?
N2 N1 B1 124.77(13) . . ?
C2 N1 B1 121.08(13) . . ?
N1 N2 C1 117.15(14) . . ?
N4 N3 C8 114.04(13) . . ?
N4 N3 B1 122.58(14) . . ?
C8 N3 B1 123.15(13) . . ?
N3 N4 C1 119.12(14) . . ?
N4 C1 N2 126.24(15) . . ?
N4 C1 C14 116.35(14) . . ?
N2 C1 C14 117.30(15) . . ?
F1 B1 F2 111.86(15) . . ?
F1 B1 N3 111.21(15) . . ?
F2 B1 N3 109.07(14) . . ?
F1 B1 N1 109.16(14) . . ?
F2 B1 N1 110.47(15) . . ?
N3 B1 N1 104.84(13) . . ?
C7 C2 C3 120.92(16) . . ?
C7 C2 N1 120.48(15) . . ?
C3 C2 N1 118.58(15) . . ?
C4 C3 C2 118.77(17) . . ?
C4 C3 H3 120.9(10) . . ?
C2 C3 H3 120.3(10) . . ?
C5 C4 C3 120.89(17) . . ?
C5 C4 H4 119.2(11) . . ?
C3 C4 H4 119.9(11) . . ?
C4 C5 C6 120.05(17) . . ?
C4 C5 H5 118.7(10) . . ?
C6 C5 H5 121.2(10) . . ?
C7 C6 C5 120.13(17) . . ?
C7 C6 H6 118.8(10) . . ?
C5 C6 H6 121.0(10) . . ?
C2 C7 C6 119.23(16) . . ?
C2 C7 H7 116.4(11) . . ?
C6 C7 H7 124.3(11) . . ?
C13 C8 C9 120.05(17) . . ?
C13 C8 N3 120.55(15) . . ?
C9 C8 N3 119.38(15) . . ?
C10 C9 C8 119.29(18) . . ?
C10 C9 H9 121.6(10) . . ?
C8 C9 H9 119.0(10) . . ?
C11 C10 C9 120.69(18) . . ?
C11 C10 H10 119.7(11) . . ?
C9 C10 H10 119.6(11) . . ?
C10 C11 C12 119.84(18) . . ?
C10 C11 H11 120.2(12) . . ?
C12 C11 H11 120.0(12) . . ?
C11 C12 C13 120.58(18) . . ?
C11 C12 H12 120.7(11) . . ?
C13 C12 H12 118.7(11) . . ?
C12 C13 C8 119.56(17) . . ?
C12 C13 H13 118.7(10) . . ?
C8 C13 H13 121.7(10) . . ?
C15 C14 C19 119.26(15) . . ?
C15 C14 C1 118.41(15) . . ?
C19 C14 C1 122.28(15) . . ?
C14 C15 C16 121.15(16) . . ?
C14 C15 H15 120.6(10) . . ?
C16 C15 H15 118.2(10) . . ?
C15 C16 C17 119.01(15) . . ?
C15 C16 C20 118.14(15) . . ?
C17 C16 C20 122.82(14) . . ?
C18 C17 C16 119.82(16) . . ?
C18 C17 H17 118.8(10) . . ?
C16 C17 H17 121.3(10) . . ?
C17 C18 C19 121.11(17) . . ?
C17 C18 H18 120.3(11) . . ?
C19 C18 H18 118.6(11) . . ?
C18 C19 C14 119.60(17) . . ?
C18 C19 H19 121.8(11) . . ?
C14 C19 H19 118.6(11) . . ?
N6 N5 C21 114.35(13) . . ?
N6 N5 B2 118.99(14) . . ?
C21 N5 B2 126.66(14) . . ?
N5 N6 C20 118.14(13) . . ?
N8 N7 C27 113.96(13) . . ?
N8 N7 B2 119.82(13) . . ?
C27 N7 B2 126.18(13) . . ?
N7 N8 C20 117.02(14) . . ?
N8 C20 N6 124.37(15) . . ?
N8 C20 C16 118.54(15) . . ?
N6 C20 C16 116.36(14) . . ?
F3 B2 F4 111.91(15) . . ?
F3 B2 N5 111.84(15) . . ?
F4 B2 N5 108.59(14) . . ?
F3 B2 N7 112.65(14) . . ?
F4 B2 N7 109.15(15) . . ?
N5 B2 N7 102.22(13) . . ?
C22 C21 C26 120.57(16) . . ?
C22 C21 N5 119.87(15) . . ?
C26 C21 N5 119.53(15) . . ?
C23 C22 C21 119.38(17) . . ?
C23 C22 H22 121.3(11) . . ?
C21 C22 H22 119.3(10) . . ?
C24 C23 C22 120.57(18) . . ?
C24 C23 H23 120.1(12) . . ?
C22 C23 H23 119.3(12) . . ?
C23 C24 C25 119.77(18) . . ?
C23 C24 H24 120.8(11) . . ?
C25 C24 H24 119.5(10) . . ?
C26 C25 C24 120.54(18) . . ?
C26 C25 H25 119.3(12) . . ?
C24 C25 H25 120.2(12) . . ?
C25 C26 C21 119.16(17) . . ?
C25 C26 H26 121.2(10) . . ?
C21 C26 H26 119.6(10) . . ?
C28 C27 C32 120.29(15) . . ?
C28 C27 N7 120.00(15) . . ?
C32 C27 N7 119.69(15) . . ?
C29 C28 C27 119.33(18) . . ?
C29 C28 H28 121.5(11) . . ?
C27 C28 H28 119.1(11) . . ?
C30 C29 C28 120.57(18) . . ?
C30 C29 H29 121.6(12) . . ?
C28 C29 H29 117.8(12) . . ?
C29 C30 C31 119.82(17) . . ?
C29 C30 H30 122.0(11) . . ?
C31 C30 H30 118.2(11) . . ?
C32 C31 C30 120.33(18) . . ?
C32 C31 H31 119.0(12) . . ?
C30 C31 H31 120.6(12) . . ?
C31 C32 C27 119.64(17) . . ?
C31 C32 H32 120.4(10) . . ?
C27 C32 H32 119.9(10) . . ?

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
C2 N1 N2 C1 -174.58(14) . . . . ?
B1 N1 N2 C1 7.1(2) . . . . ?
C8 N3 N4 C1 174.00(14) . . . . ?
B1 N3 N4 C1 -11.4(2) . . . . ?
N3 N4 C1 N2 -8.8(3) . . . . ?
N3 N4 C1 C14 175.03(14) . . . . ?
N1 N2 C1 N4 10.9(2) . . . . ?
N1 N2 C1 C14 -172.92(14) . . . . ?
N4 N3 B1 F1 141.57(15) . . . . ?
C8 N3 B1 F1 -44.3(2) . . . . ?
N4 N3 B1 F2 -94.59(18) . . . . ?
C8 N3 B1 F2 79.57(19) . . . . ?
N4 N3 B1 N1 23.7(2) . . . . ?
C8 N3 B1 N1 -162.12(14) . . . . ?
N2 N1 B1 F1 -141.16(15) . . . . ?
C2 N1 B1 F1 40.7(2) . . . . ?
N2 N1 B1 F2 95.43(18) . . . . ?
C2 N1 B1 F2 -82.72(18) . . . . ?
N2 N1 B1 N3 -21.9(2) . . . . ?
C2 N1 B1 N3 159.91(14) . . . . ?
N2 N1 C2 C7 32.4(2) . . . . ?
B1 N1 C2 C7 -149.31(16) . . . . ?
N2 N1 C2 C3 -146.55(15) . . . . ?
B1 N1 C2 C3 31.8(2) . . . . ?
C7 C2 C3 C4 -1.3(2) . . . . ?
N1 C2 C3 C4 177.58(15) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
N1 C2 C7 C6 -177.81(15) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
N4 N3 C8 C13 -13.4(2) . . . . ?
B1 N3 C8 C13 171.96(15) . . . . ?
N4 N3 C8 C9 164.85(15) . . . . ?
B1 N3 C8 C9 -9.8(2) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
N3 C8 C9 C10 -178.86(16) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
N3 C8 C13 C12 178.48(15) . . . . ?
N4 C1 C14 C15 -7.1(2) . . . . ?
N2 C1 C14 C15 176.40(15) . . . . ?
N4 C1 C14 C19 175.29(16) . . . . ?
N2 C1 C14 C19 -1.2(2) . . . . ?
C19 C14 C15 C16 0.7(3) . . . . ?
C1 C14 C15 C16 -177.00(16) . . . . ?
C14 C15 C16 C17 -1.9(3) . . . . ?
C14 C15 C16 C20 175.93(15) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C20 C16 C17 C18 -176.55(16) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C14 -1.9(3) . . . . ?
C15 C14 C19 C18 1.2(3) . . . . ?
C1 C14 C19 C18 178.80(16) . . . . ?
C21 N5 N6 C20 -164.44(14) . . . . ?
B2 N5 N6 C20 16.0(2) . . . . ?
C27 N7 N8 C20 165.92(13) . . . . ?
B2 N7 N8 C20 -16.3(2) . . . . ?
N7 N8 C20 N6 -19.6(2) . . . . ?
N7 N8 C20 C16 170.60(14) . . . . ?
N5 N6 C20 N8 19.7(2) . . . . ?
N5 N6 C20 C16 -170.22(14) . . . . ?
C15 C16 C20 N8 179.25(15) . . . . ?
C17 C16 C20 N8 -3.0(2) . . . . ?
C15 C16 C20 N6 8.6(2) . . . . ?
C17 C16 C20 N6 -173.68(15) . . . . ?
N6 N5 B2 F3 -163.23(14) . . . . ?
C21 N5 B2 F3 17.3(2) . . . . ?
N6 N5 B2 F4 72.80(18) . . . . ?
C21 N5 B2 F4 -106.65(18) . . . . ?
N6 N5 B2 N7 -42.47(18) . . . . ?
C21 N5 B2 N7 138.08(15) . . . . ?
N8 N7 B2 F3 163.08(14) . . . . ?
C27 N7 B2 F3 -19.4(2) . . . . ?
N8 N7 B2 F4 -71.97(18) . . . . ?
C27 N7 B2 F4 105.53(17) . . . . ?
N8 N7 B2 N5 42.89(19) . . . . ?
C27 N7 B2 N5 -139.60(15) . . . . ?
N6 N5 C21 C22 -153.70(15) . . . . ?
B2 N5 C21 C22 25.8(2) . . . . ?
N6 N5 C21 C26 24.4(2) . . . . ?
B2 N5 C21 C26 -156.14(16) . . . . ?
C26 C21 C22 C23 0.0(2) . . . . ?
N5 C21 C22 C23 178.04(15) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 -0.1(3) . . . . ?
C22 C21 C26 C25 0.3(2) . . . . ?
N5 C21 C26 C25 -177.74(15) . . . . ?
N8 N7 C27 C28 156.92(15) . . . . ?
B2 N7 C27 C28 -20.7(2) . . . . ?
N8 N7 C27 C32 -21.7(2) . . . . ?
B2 N7 C27 C32 160.68(16) . . . . ?
C32 C27 C28 C29 -0.2(3) . . . . ?
N7 C27 C28 C29 -178.83(15) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C31 0.9(3) . . . . ?
C29 C30 C31 C32 -1.1(3) . . . . ?
C30 C31 C32 C27 0.7(3) . . . . ?
C28 C27 C32 C31 0.0(3) . . . . ?
N7 C27 C32 C31 178.60(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 F2 0.954(18) 2.534(17) 3.182(2) 125.3(13) .
C9 H9 F1 0.981(18) 2.338(17) 2.892(2) 114.9(12) .
C22 H22 F3 0.940(18) 2.342(17) 2.859(2) 114.2(13) .
C28 H28 F3 0.927(19) 2.291(17) 2.835(2) 117.0(13) .

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.054
_shelxl_version_number           2014/6

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
