# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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data_TBT-1
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            TBT-1
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H47 B F2 N4 O'
_chemical_formula_sum            'C56 H47 B F2 N4 O'
_chemical_formula_weight         840.79

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   11.0667(5)
_cell_length_b                   13.6645(6)
_cell_length_c                   16.4680(6)
_cell_angle_alpha                73.484(4)
_cell_angle_beta                 86.016(3)
_cell_angle_gamma                72.070(4)
_cell_volume                     2271.16(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      28.240

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      1.230
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    multi-scan
_exptl_crystal_F_000             884
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18242
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.1005
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         28.24
_reflns_number_total             9289
_reflns_number_gt                4465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0685P)²+0.6071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9289
_refine_ls_number_parameters     582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1580
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.6787(4) 0.3983(3) 0.0616(2) 0.0432(9) Uani 1 1 d . . .
C2 C 0.7822(3) 0.5196(3) -0.05577(19) 0.0423(8) Uani 1 1 d . . .
C3 C 0.8534(3) 0.5109(3) -0.1295(2) 0.0456(8) Uani 1 1 d . . .
C4 C 0.8696(3) 0.4090(3) -0.13682(19) 0.0445(8) Uani 1 1 d . . .
C5 C 0.8045(3) 0.3578(3) -0.06969(19) 0.0433(8) Uani 1 1 d . . .
C6 C 0.8968(4) 0.5962(3) -0.1932(2) 0.0629(11) Uani 1 1 d . . .
H6A H 0.8297 0.6628 -0.2046 0.094 Uiso 1 1 calc R . .
H6B H 0.9185 0.5757 -0.2448 0.094 Uiso 1 1 calc R . .
H6C H 0.9699 0.6043 -0.1710 0.094 Uiso 1 1 calc R . .
C7 C 0.7905(4) 0.2483(3) -0.0502(2) 0.0567(10) Uani 1 1 d . . .
H7A H 0.7923 0.2179 0.0101 0.085 Uiso 1 1 calc R . .
H7B H 0.8591 0.2039 -0.0748 0.085 Uiso 1 1 calc R . .
H7C H 0.7112 0.2527 -0.0734 0.085 Uiso 1 1 calc R . .
C8 C 0.9481(3) 0.3604(3) -0.20013(19) 0.0439(8) Uani 1 1 d . . .
C9 C 1.0708(3) 0.3676(3) -0.2141(2) 0.0509(9) Uani 1 1 d . . .
H9 H 1.1014 0.4037 -0.1842 0.061 Uiso 1 1 calc R . .
C10 C 1.1482(3) 0.3220(3) -0.2716(2) 0.0521(9) Uani 1 1 d . . .
H10 H 1.2294 0.3290 -0.2808 0.063 Uiso 1 1 calc R . .
C11 C 1.1058(3) 0.2666(3) -0.3152(2) 0.0477(9) Uani 1 1 d . . .
C12 C 0.9838(4) 0.2594(3) -0.3026(2) 0.0527(9) Uani 1 1 d . . .
H12 H 0.9538 0.2225 -0.3321 0.063 Uiso 1 1 calc R . .
C13 C 0.9060(3) 0.3072(3) -0.2460(2) 0.0504(9) Uani 1 1 d . . .
H13 H 0.8234 0.3030 -0.2389 0.061 Uiso 1 1 calc R . .
C14 C 1.2166(3) 0.2822(3) -0.4493(2) 0.0502(9) Uani 1 1 d . . .
C15 C 1.1189(4) 0.3579(3) -0.5005(2) 0.0642(11) Uani 1 1 d . . .
H15 H 1.0353 0.3637 -0.4844 0.077 Uiso 1 1 calc R . .
C16 C 1.1430(4) 0.4249(3) -0.5750(2) 0.0725(12) Uani 1 1 d . . .
H16 H 1.0757 0.4757 -0.6087 0.087 Uiso 1 1 calc R . .
C17 C 1.2649(4) 0.4179(4) -0.6003(3) 0.0755(12) Uani 1 1 d . . .
H17 H 1.2810 0.4633 -0.6509 0.091 Uiso 1 1 calc R . .
C18 C 1.3624(4) 0.3437(4) -0.5502(3) 0.0831(13) Uani 1 1 d . . .
H18 H 1.4456 0.3376 -0.5673 0.100 Uiso 1 1 calc R . .
C19 C 1.3395(4) 0.2770(3) -0.4743(3) 0.0679(11) Uani 1 1 d . . .
H19 H 1.4073 0.2283 -0.4398 0.082 Uiso 1 1 calc R . .
C20 C 1.2616(3) 0.1080(3) -0.3408(2) 0.0556(10) Uani 1 1 d . . .
C21 C 1.3212(4) 0.0478(3) -0.3961(3) 0.0773(12) Uani 1 1 d . . .
H21 H 1.3121 0.0790 -0.4542 0.093 Uiso 1 1 calc R . .
C22 C 1.3929(5) -0.0568(4) -0.3655(5) 0.1033(18) Uani 1 1 d . . .
H22 H 1.4330 -0.0952 -0.4033 0.124 Uiso 1 1 calc R . .
C23 C 1.4065(6) -0.1057(4) -0.2807(5) 0.116(2) Uani 1 1 d . . .
H23 H 1.4561 -0.1766 -0.2606 0.140 Uiso 1 1 calc R . .
C24 C 1.3460(5) -0.0489(4) -0.2255(4) 0.1081(18) Uani 1 1 d . . .
H24 H 1.3526 -0.0824 -0.1676 0.130 Uiso 1 1 calc R . .
C25 C 1.2751(4) 0.0575(3) -0.2545(3) 0.0791(13) Uani 1 1 d . . .
H25 H 1.2363 0.0953 -0.2160 0.095 Uiso 1 1 calc R . .
C26 C 0.7403(3) 0.6030(2) -0.01694(19) 0.0408(8) Uani 1 1 d . . .
C27 C 0.7754(3) 0.7025(3) -0.05524(19) 0.0410(8) Uani 1 1 d . . .
C28 C 0.8975(3) 0.7046(3) -0.0468(2) 0.0501(9) Uani 1 1 d . . .
H28 H 0.9574 0.6435 -0.0155 0.060 Uiso 1 1 calc R . .
C29 C 0.9327(4) 0.7956(3) -0.0840(2) 0.0621(11) Uani 1 1 d . . .
H29 H 1.0155 0.7958 -0.0781 0.074 Uiso 1 1 calc R . .
C30 C 0.8438(4) 0.8857(3) -0.1298(3) 0.0654(11) Uani 1 1 d . . .
C31 C 0.7210(4) 0.8851(3) -0.1386(3) 0.0663(11) Uani 1 1 d . . .
H31 H 0.6609 0.9466 -0.1692 0.080 Uiso 1 1 calc R . .
C32 C 0.6877(3) 0.7945(3) -0.1024(2) 0.0543(10) Uani 1 1 d . . .
H32 H 0.6051 0.7944 -0.1094 0.065 Uiso 1 1 calc R . .
C33 C 0.9968(5) 0.9805(4) -0.1697(5) 0.148(3) Uani 1 1 d . . .
H33A H 1.0021 1.0496 -0.2020 0.223 Uiso 1 1 calc R . .
H33B H 1.0487 0.9269 -0.1950 0.223 Uiso 1 1 calc R . .
H33C H 1.0262 0.9656 -0.1127 0.223 Uiso 1 1 calc R . .
C34 C 0.6686(3) 0.5944(3) 0.05554(19) 0.0413(8) Uani 1 1 d . . .
C35 C 0.6166(3) 0.6666(3) 0.1054(2) 0.0439(8) Uani 1 1 d . . .
C36 C 0.5490(3) 0.6170(3) 0.16914(19) 0.0423(8) Uani 1 1 d . . .
C37 C 0.5578(3) 0.5158(3) 0.1575(2) 0.0451(8) Uani 1 1 d . . .
C38 C 0.6336(3) 0.7742(3) 0.0948(2) 0.0564(10) Uani 1 1 d . . .
H38A H 0.7197 0.7714 0.0797 0.085 Uiso 1 1 calc R . .
H38B H 0.6150 0.7934 0.1470 0.085 Uiso 1 1 calc R . .
H38C H 0.5770 0.8266 0.0508 0.085 Uiso 1 1 calc R . .
C39 C 0.4941(3) 0.4367(3) 0.2055(2) 0.0554(10) Uani 1 1 d . . .
H39A H 0.4663 0.4063 0.1671 0.083 Uiso 1 1 calc R . .
H39B H 0.4221 0.4716 0.2338 0.083 Uiso 1 1 calc R . .
H39C H 0.5526 0.3810 0.2466 0.083 Uiso 1 1 calc R . .
C40 C 0.4803(3) 0.6605(3) 0.2379(2) 0.0446(8) Uani 1 1 d . . .
C41 C 0.3989(3) 0.7640(3) 0.2211(2) 0.0461(8) Uani 1 1 d . . .
H41 H 0.3867 0.8067 0.1654 0.055 Uiso 1 1 calc R . .
C42 C 0.3353(3) 0.8056(3) 0.2846(2) 0.0452(8) Uani 1 1 d . . .
H42 H 0.2804 0.8751 0.2711 0.054 Uiso 1 1 calc R . .
C43 C 0.3527(3) 0.7447(3) 0.3684(2) 0.0440(8) Uani 1 1 d . . .
C44 C 0.4358(3) 0.6406(3) 0.3865(2) 0.0527(9) Uani 1 1 d . . .
H44 H 0.4503 0.5984 0.4423 0.063 Uiso 1 1 calc R . .
C45 C 0.4960(3) 0.6003(3) 0.3220(2) 0.0512(9) Uani 1 1 d . . .
H45 H 0.5493 0.5301 0.3352 0.061 Uiso 1 1 calc R . .
C46 C 0.2577(3) 0.7245(3) 0.5108(2) 0.0479(9) Uani 1 1 d . . .
C47 C 0.2554(3) 0.7558(3) 0.5839(2) 0.0602(10) Uani 1 1 d . . .
H47 H 0.2763 0.8173 0.5821 0.072 Uiso 1 1 calc R . .
C48 C 0.2220(4) 0.6954(4) 0.6598(2) 0.0688(12) Uani 1 1 d . . .
H48 H 0.2208 0.7169 0.7087 0.083 Uiso 1 1 calc R . .
C49 C 0.1909(4) 0.6051(4) 0.6641(3) 0.0750(13) Uani 1 1 d . . .
H49 H 0.1683 0.5652 0.7154 0.090 Uiso 1 1 calc R . .
C50 C 0.1935(4) 0.5737(3) 0.5914(3) 0.0709(12) Uani 1 1 d . . .
H50 H 0.1739 0.5115 0.5938 0.085 Uiso 1 1 calc R . .
C51 C 0.2249(3) 0.6335(3) 0.5154(2) 0.0553(9) Uani 1 1 d . . .
H51 H 0.2240 0.6124 0.4665 0.066 Uiso 1 1 calc R . .
C52 C 0.2343(4) 0.9025(3) 0.4142(2) 0.0560(10) Uani 1 1 d . . .
C53 C 0.3094(4) 0.9690(3) 0.3926(2) 0.0706(12) Uani 1 1 d . . .
H53 H 0.3972 0.9406 0.3918 0.085 Uiso 1 1 calc R . .
C54 C 0.2531(6) 1.0792(4) 0.3719(3) 0.0928(15) Uani 1 1 d . . .
H54 H 0.3036 1.1246 0.3570 0.111 Uiso 1 1 calc R . .
C55 C 0.1242(7) 1.1212(4) 0.3732(3) 0.1039(19) Uani 1 1 d . . .
H55 H 0.0868 1.1950 0.3599 0.125 Uiso 1 1 calc R . .
C56 C 0.0506(5) 1.0544(4) 0.3942(3) 0.1045(18) Uani 1 1 d . . .
H56 H -0.0372 1.0830 0.3947 0.125 Uiso 1 1 calc R . .
C57 C 0.1047(4) 0.9452(4) 0.4149(3) 0.0782(13) Uani 1 1 d . . .
H57 H 0.0535 0.9004 0.4292 0.094 Uiso 1 1 calc R . .
N1 N 0.7531(2) 0.4241(2) -0.02099(15) 0.0407(7) Uani 1 1 d . . .
N2 N 0.6306(2) 0.5020(2) 0.09041(15) 0.0413(7) Uani 1 1 d . . .
N3 N 1.1887(3) 0.2143(2) -0.37196(18) 0.0575(8) Uani 1 1 d . . .
N4 N 0.2901(3) 0.7884(2) 0.43351(17) 0.0544(8) Uani 1 1 d . . .
O1 O 0.8692(3) 0.9798(2) -0.1689(2) 0.1073(12) Uani 1 1 d . . .
F1 F 0.75805(19) 0.31853(15) 0.12390(11) 0.0640(6) Uani 1 1 d . . .
F2 F 0.57851(19) 0.36507(16) 0.04722(13) 0.0635(6) 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
B1 F2 1.379(4) . ?
B1 F1 1.383(4) . ?
B1 N2 1.549(5) . ?
B1 N1 1.550(4) . ?
C2 N1 1.394(4) . ?
C2 C26 1.403(4) . ?
C2 C3 1.414(4) . ?
C3 C4 1.387(4) . ?
C3 C6 1.507(4) . ?
C4 C5 1.411(4) . ?
C4 C8 1.481(4) . ?
C5 N1 1.349(4) . ?
C5 C7 1.493(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.373(5) . ?
C8 C9 1.391(5) . ?
C9 C10 1.382(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(5) . ?
C11 N3 1.444(4) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.376(5) . ?
C14 C19 1.379(5) . ?
C14 N3 1.424(4) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.388(5) . ?
C20 N3 1.391(4) . ?
C20 C21 1.396(5) . ?
C21 C22 1.369(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.383(6) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C34 1.384(4) . ?
C26 C27 1.484(4) . ?
C27 C28 1.378(4) . ?
C27 C32 1.387(4) . ?
C28 C29 1.380(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(5) . ?
C29 H29 0.9300 . ?
C30 O1 1.368(4) . ?
C30 C31 1.380(5) . ?
C31 C32 1.361(5) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 O1 1.414(5) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 N2 1.407(4) . ?
C34 C35 1.422(4) . ?
C35 C36 1.386(4) . ?
C35 C38 1.498(4) . ?
C36 C37 1.423(4) . ?
C36 C40 1.483(4) . ?
C37 N2 1.344(4) . ?
C37 C39 1.481(4) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C41 1.383(4) . ?
C40 C45 1.387(4) . ?
C41 C42 1.379(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.385(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.397(4) . ?
C43 N4 1.411(4) . ?
C44 C45 1.372(4) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C46 C51 1.381(5) . ?
C46 C47 1.383(5) . ?
C46 N4 1.417(4) . ?
C47 C48 1.384(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.362(6) . ?
C48 H48 0.9300 . ?
C49 C50 1.378(6) . ?
C49 H49 0.9300 . ?
C50 C51 1.374(5) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 C57 1.373(5) . ?
C52 C53 1.373(5) . ?
C52 N4 1.437(4) . ?
C53 C54 1.389(6) . ?
C53 H53 0.9300 . ?
C54 C55 1.366(7) . ?
C54 H54 0.9300 . ?
C55 C56 1.362(7) . ?
C55 H55 0.9300 . ?
C56 C57 1.374(6) . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?

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
F2 B1 F1 109.1(3) . . ?
F2 B1 N2 110.9(3) . . ?
F1 B1 N2 109.3(3) . . ?
F2 B1 N1 110.4(3) . . ?
F1 B1 N1 110.1(3) . . ?
N2 B1 N1 107.1(3) . . ?
N1 C2 C26 120.1(3) . . ?
N1 C2 C3 108.0(3) . . ?
C26 C2 C3 131.9(3) . . ?
C4 C3 C2 107.0(3) . . ?
C4 C3 C6 124.8(3) . . ?
C2 C3 C6 128.1(3) . . ?
C3 C4 C5 107.5(3) . . ?
C3 C4 C8 126.1(3) . . ?
C5 C4 C8 126.3(3) . . ?
N1 C5 C4 109.2(3) . . ?
N1 C5 C7 122.1(3) . . ?
C4 C5 C7 128.7(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 117.6(3) . . ?
C13 C8 C4 123.2(3) . . ?
C9 C8 C4 119.2(3) . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 N3 120.4(3) . . ?
C12 C11 N3 120.3(3) . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 121.5(3) . . ?
C8 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C19 118.1(3) . . ?
C15 C14 N3 119.7(3) . . ?
C19 C14 N3 122.3(3) . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.0(4) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 120.4(4) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C25 C20 N3 121.6(4) . . ?
C25 C20 C21 117.8(4) . . ?
N3 C20 C21 120.6(4) . . ?
C22 C21 C20 120.7(5) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 121.2(5) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.0(5) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C23 C24 C25 121.0(5) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C20 120.3(5) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C34 C26 C2 122.0(3) . . ?
C34 C26 C27 119.7(3) . . ?
C2 C26 C27 118.3(3) . . ?
C28 C27 C32 118.3(3) . . ?
C28 C27 C26 120.5(3) . . ?
C32 C27 C26 121.1(3) . . ?
C27 C28 C29 121.3(3) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C30 C29 C28 119.1(3) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
O1 C30 C29 123.6(4) . . ?
O1 C30 C31 116.1(3) . . ?
C29 C30 C31 120.3(3) . . ?
C32 C31 C30 120.1(3) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.8(3) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?
O1 C33 H33A 109.5 . . ?
O1 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O1 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C26 C34 N2 120.1(3) . . ?
C26 C34 C35 131.9(3) . . ?
N2 C34 C35 108.0(3) . . ?
C36 C35 C34 106.8(3) . . ?
C36 C35 C38 125.4(3) . . ?
C34 C35 C38 127.8(3) . . ?
C35 C36 C37 107.8(3) . . ?
C35 C36 C40 126.5(3) . . ?
C37 C36 C40 125.7(3) . . ?
N2 C37 C36 109.2(3) . . ?
N2 C37 C39 122.5(3) . . ?
C36 C37 C39 128.3(3) . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 C45 116.9(3) . . ?
C41 C40 C36 121.4(3) . . ?
C45 C40 C36 121.7(3) . . ?
C42 C41 C40 121.9(3) . . ?
C42 C41 H41 119.1 . . ?
C40 C41 H41 119.1 . . ?
C41 C42 C43 120.5(3) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 H42 119.7 . . ?
C42 C43 C44 118.2(3) . . ?
C42 C43 N4 120.5(3) . . ?
C44 C43 N4 121.3(3) . . ?
C45 C44 C43 120.1(3) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C44 C45 C40 122.3(3) . . ?
C44 C45 H45 118.9 . . ?
C40 C45 H45 118.9 . . ?
C51 C46 C47 118.7(3) . . ?
C51 C46 N4 122.2(3) . . ?
C47 C46 N4 119.1(3) . . ?
C46 C47 C48 120.0(4) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C49 C48 C47 121.1(4) . . ?
C49 C48 H48 119.4 . . ?
C47 C48 H48 119.4 . . ?
C48 C49 C50 119.0(4) . . ?
C48 C49 H49 120.5 . . ?
C50 C49 H49 120.5 . . ?
C51 C50 C49 120.6(4) . . ?
C51 C50 H50 119.7 . . ?
C49 C50 H50 119.7 . . ?
C50 C51 C46 120.7(4) . . ?
C50 C51 H51 119.7 . . ?
C46 C51 H51 119.7 . . ?
C57 C52 C53 119.8(4) . . ?
C57 C52 N4 119.7(4) . . ?
C53 C52 N4 120.5(4) . . ?
C52 C53 C54 119.5(4) . . ?
C52 C53 H53 120.2 . . ?
C54 C53 H53 120.2 . . ?
C55 C54 C53 120.4(5) . . ?
C55 C54 H54 119.8 . . ?
C53 C54 H54 119.8 . . ?
C56 C55 C54 119.5(5) . . ?
C56 C55 H55 120.2 . . ?
C54 C55 H55 120.2 . . ?
C55 C56 C57 120.8(5) . . ?
C55 C56 H56 119.6 . . ?
C57 C56 H56 119.6 . . ?
C52 C57 C56 119.9(5) . . ?
C52 C57 H57 120.0 . . ?
C56 C57 H57 120.0 . . ?
C5 N1 C2 108.3(3) . . ?
C5 N1 B1 126.5(3) . . ?
C2 N1 B1 125.2(3) . . ?
C37 N2 C34 108.3(3) . . ?
C37 N2 B1 126.6(3) . . ?
C34 N2 B1 124.8(3) . . ?
C20 N3 C14 122.3(3) . . ?
C20 N3 C11 119.0(3) . . ?
C14 N3 C11 116.5(3) . . ?
C43 N4 C46 122.5(3) . . ?
C43 N4 C52 118.3(3) . . ?
C46 N4 C52 117.9(3) . . ?
C30 O1 C33 118.0(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
N1 C2 C3 C4 -1.8(4) . . . . ?
C26 C2 C3 C4 178.7(3) . . . . ?
N1 C2 C3 C6 174.0(3) . . . . ?
C26 C2 C3 C6 -5.6(6) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
C6 C3 C4 C5 -173.8(3) . . . . ?
C2 C3 C4 C8 -174.1(3) . . . . ?
C6 C3 C4 C8 10.0(5) . . . . ?
C3 C4 C5 N1 -1.8(4) . . . . ?
C8 C4 C5 N1 174.5(3) . . . . ?
C3 C4 C5 C7 178.7(3) . . . . ?
C8 C4 C5 C7 -5.1(6) . . . . ?
C3 C4 C8 C13 -133.3(4) . . . . ?
C5 C4 C8 C13 51.1(5) . . . . ?
C3 C4 C8 C9 47.2(5) . . . . ?
C5 C4 C8 C9 -128.4(4) . . . . ?
C13 C8 C9 C10 -0.5(5) . . . . ?
C4 C8 C9 C10 179.0(3) . . . . ?
C8 C9 C10 C11 -1.3(5) . . . . ?
C9 C10 C11 C12 1.8(5) . . . . ?
C9 C10 C11 N3 -176.8(3) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
N3 C11 C12 C13 178.1(3) . . . . ?
C9 C8 C13 C12 1.8(5) . . . . ?
C4 C8 C13 C12 -177.7(3) . . . . ?
C11 C12 C13 C8 -1.3(5) . . . . ?
C19 C14 C15 C16 1.1(6) . . . . ?
N3 C14 C15 C16 179.5(4) . . . . ?
C14 C15 C16 C17 0.2(7) . . . . ?
C15 C16 C17 C18 -0.3(7) . . . . ?
C16 C17 C18 C19 -0.9(7) . . . . ?
C15 C14 C19 C18 -2.4(6) . . . . ?
N3 C14 C19 C18 179.4(4) . . . . ?
C17 C18 C19 C14 2.3(7) . . . . ?
C25 C20 C21 C22 -1.6(6) . . . . ?
N3 C20 C21 C22 -179.9(4) . . . . ?
C20 C21 C22 C23 1.2(8) . . . . ?
C21 C22 C23 C24 0.7(9) . . . . ?
C22 C23 C24 C25 -2.0(9) . . . . ?
C23 C24 C25 C20 1.6(8) . . . . ?
N3 C20 C25 C24 178.6(4) . . . . ?
C21 C20 C25 C24 0.2(6) . . . . ?
N1 C2 C26 C34 -0.7(5) . . . . ?
C3 C2 C26 C34 178.8(3) . . . . ?
N1 C2 C26 C27 178.9(3) . . . . ?
C3 C2 C26 C27 -1.5(5) . . . . ?
C34 C26 C27 C28 105.3(4) . . . . ?
C2 C26 C27 C28 -74.3(4) . . . . ?
C34 C26 C27 C32 -76.6(4) . . . . ?
C2 C26 C27 C32 103.7(4) . . . . ?
C32 C27 C28 C29 0.1(5) . . . . ?
C26 C27 C28 C29 178.2(3) . . . . ?
C27 C28 C29 C30 0.4(6) . . . . ?
C28 C29 C30 O1 179.9(4) . . . . ?
C28 C29 C30 C31 -0.1(6) . . . . ?
O1 C30 C31 C32 179.4(4) . . . . ?
C29 C30 C31 C32 -0.6(6) . . . . ?
C30 C31 C32 C27 1.1(6) . . . . ?
C28 C27 C32 C31 -0.8(5) . . . . ?
C26 C27 C32 C31 -178.9(3) . . . . ?
C2 C26 C34 N2 -2.9(5) . . . . ?
C27 C26 C34 N2 177.5(3) . . . . ?
C2 C26 C34 C35 179.8(3) . . . . ?
C27 C26 C34 C35 0.2(5) . . . . ?
C26 C34 C35 C36 177.7(3) . . . . ?
N2 C34 C35 C36 0.2(3) . . . . ?
C26 C34 C35 C38 -4.3(6) . . . . ?
N2 C34 C35 C38 178.1(3) . . . . ?
C34 C35 C36 C37 -0.9(4) . . . . ?
C38 C35 C36 C37 -179.0(3) . . . . ?
C34 C35 C36 C40 178.6(3) . . . . ?
C38 C35 C36 C40 0.5(5) . . . . ?
C35 C36 C37 N2 1.4(4) . . . . ?
C40 C36 C37 N2 -178.1(3) . . . . ?
C35 C36 C37 C39 -175.2(3) . . . . ?
C40 C36 C37 C39 5.3(5) . . . . ?
C35 C36 C40 C41 48.0(5) . . . . ?
C37 C36 C40 C41 -132.6(4) . . . . ?
C35 C36 C40 C45 -131.0(4) . . . . ?
C37 C36 C40 C45 48.4(5) . . . . ?
C45 C40 C41 C42 -0.5(5) . . . . ?
C36 C40 C41 C42 -179.5(3) . . . . ?
C40 C41 C42 C43 0.9(5) . . . . ?
C41 C42 C43 C44 -0.1(5) . . . . ?
C41 C42 C43 N4 178.3(3) . . . . ?
C42 C43 C44 C45 -1.2(5) . . . . ?
N4 C43 C44 C45 -179.6(3) . . . . ?
C43 C44 C45 C40 1.7(6) . . . . ?
C41 C40 C45 C44 -0.8(5) . . . . ?
C36 C40 C45 C44 178.2(3) . . . . ?
C51 C46 C47 C48 0.7(5) . . . . ?
N4 C46 C47 C48 179.0(3) . . . . ?
C46 C47 C48 C49 0.0(6) . . . . ?
C47 C48 C49 C50 0.2(6) . . . . ?
C48 C49 C50 C51 -1.1(6) . . . . ?
C49 C50 C51 C46 1.7(6) . . . . ?
C47 C46 C51 C50 -1.5(5) . . . . ?
N4 C46 C51 C50 -179.8(3) . . . . ?
C57 C52 C53 C54 0.3(6) . . . . ?
N4 C52 C53 C54 178.2(3) . . . . ?
C52 C53 C54 C55 0.2(7) . . . . ?
C53 C54 C55 C56 -0.7(8) . . . . ?
C54 C55 C56 C57 0.6(8) . . . . ?
C53 C52 C57 C56 -0.3(6) . . . . ?
N4 C52 C57 C56 -178.3(4) . . . . ?
C55 C56 C57 C52 -0.1(8) . . . . ?
C4 C5 N1 C2 0.7(4) . . . . ?
C7 C5 N1 C2 -179.7(3) . . . . ?
C4 C5 N1 B1 -177.1(3) . . . . ?
C7 C5 N1 B1 2.5(5) . . . . ?
C26 C2 N1 C5 -179.7(3) . . . . ?
C3 C2 N1 C5 0.7(3) . . . . ?
C26 C2 N1 B1 -1.9(5) . . . . ?
C3 C2 N1 B1 178.5(3) . . . . ?
F2 B1 N1 C5 -55.1(4) . . . . ?
F1 B1 N1 C5 65.4(4) . . . . ?
N2 B1 N1 C5 -175.9(3) . . . . ?
F2 B1 N1 C2 127.4(3) . . . . ?
F1 B1 N1 C2 -112.0(3) . . . . ?
N2 B1 N1 C2 6.7(4) . . . . ?
C36 C37 N2 C34 -1.3(3) . . . . ?
C39 C37 N2 C34 175.5(3) . . . . ?
C36 C37 N2 B1 172.1(3) . . . . ?
C39 C37 N2 B1 -11.0(5) . . . . ?
C26 C34 N2 C37 -177.2(3) . . . . ?
C35 C34 N2 C37 0.7(3) . . . . ?
C26 C34 N2 B1 9.3(4) . . . . ?
C35 C34 N2 B1 -172.8(3) . . . . ?
F2 B1 N2 C37 56.8(4) . . . . ?
F1 B1 N2 C37 -63.5(4) . . . . ?
N1 B1 N2 C37 177.3(3) . . . . ?
F2 B1 N2 C34 -130.8(3) . . . . ?
F1 B1 N2 C34 108.9(3) . . . . ?
N1 B1 N2 C34 -10.4(4) . . . . ?
C25 C20 N3 C14 149.9(4) . . . . ?
C21 C20 N3 C14 -31.8(5) . . . . ?
C25 C20 N3 C11 -12.3(5) . . . . ?
C21 C20 N3 C11 166.0(4) . . . . ?
C15 C14 N3 C20 144.7(4) . . . . ?
C19 C14 N3 C20 -37.0(5) . . . . ?
C15 C14 N3 C11 -52.6(5) . . . . ?
C19 C14 N3 C11 125.6(4) . . . . ?
C10 C11 N3 C20 91.4(4) . . . . ?
C12 C11 N3 C20 -87.2(4) . . . . ?
C10 C11 N3 C14 -71.8(4) . . . . ?
C12 C11 N3 C14 109.6(4) . . . . ?
C42 C43 N4 C46 151.9(3) . . . . ?
C44 C43 N4 C46 -29.8(5) . . . . ?
C42 C43 N4 C52 -14.9(5) . . . . ?
C44 C43 N4 C52 163.4(3) . . . . ?
C51 C46 N4 C43 -32.8(5) . . . . ?
C47 C46 N4 C43 148.9(3) . . . . ?
C51 C46 N4 C52 134.0(4) . . . . ?
C47 C46 N4 C52 -44.2(5) . . . . ?
C57 C52 N4 C43 113.1(4) . . . . ?
C53 C52 N4 C43 -64.8(5) . . . . ?
C57 C52 N4 C46 -54.3(5) . . . . ?
C53 C52 N4 C46 127.8(4) . . . . ?
C29 C30 O1 C33 7.0(7) . . . . ?
C31 C30 O1 C33 -173.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.826
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 977088'
