# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
'Junro Yoshino'
;
Department of Chemistry, Graduate School of Science,
The University of Tokyo,
7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan
;
'Naokazu Kano'
;
Department of Chemistry, Graduate School of Science,
The University of Tokyo,
7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan
;
'Takayuki Kawashima'
;
Department of Chemistry, Graduate School of Science,
The University of Tokyo,
7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan
;
_publ_contact_author_address     
;
Department of Chemistry, Graduate School of Science,
The University of Tokyo,
7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan
;
_publ_contact_author_email       takayuki@chem.s.u-tokyo.ac.jp
_publ_contact_author_fax         +81-5800-6899
_publ_contact_author_phone       +81-5800-6899
_publ_contact_author_name        'Takayuki Kawashima'
_publ_requested_category         FO
_publ_section_title              
;
The Most Intensely Fluorescent Azobenzene by Utilizing the B-N Interaction
;

data_c6f5re
_database_code_depnum_ccdc_archive 'CCDC 607217'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Bis(2,3,4,5,6-pentafluorophenyl)[2-(phenylazo)phenyl]borane
;
_chemical_name_common            
Bis(2,3,4,5,6-pentafluorophenyl)(2-(phenylazo)phenyl)borane
_chemical_melting_point          178.7-179.1
_chemical_formula_moiety         'C24 H9 B F10 N2'
_chemical_formula_sum            'C24 H9 B F10 N2'
_chemical_formula_weight         526.14

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.861(7)
_cell_length_b                   10.732(6)
_cell_length_c                   10.822(7)
_cell_angle_alpha                99.976(7)
_cell_angle_beta                 113.714(8)
_cell_angle_gamma                91.109(7)
_cell_volume                     1027.7(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3282
_cell_measurement_theta_min      3.1243
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_process_details   
;
Jacobson, R. (1998) Private communication
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           40.0000
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_number            6375
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3488
_reflns_number_gt                3068
_reflns_threshold_expression     >2sigma(I)
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury CCD (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 14.5666
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details      
;
scan:
Number of images: 600
Slice: -70.0000 - 110.0000
Image width: 0.3000
Exp time: 11.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 0.0000
XTD: 45.1689
2theta: 19.7504
scan:
Number of images: 600
Slice: -70.0000 - 110.0000
Image width: 0.3000
Exp time: 11.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 90.0000
XTD: 45.1689
2theta: 19.7504

;
_diffrn_measurement_device_details 
;
AFC8: Eulerian 3-circle
;
_diffrn_orient_matrix_UB_11      0.0946
_diffrn_orient_matrix_UB_12      -0.0096
_diffrn_orient_matrix_UB_13      0.0579
_diffrn_orient_matrix_UB_21      0.0493
_diffrn_orient_matrix_UB_22      0.0624
_diffrn_orient_matrix_UB_23      -0.0521
_diffrn_orient_matrix_UB_31      0.0158
_diffrn_orient_matrix_UB_32      0.0755
_diffrn_orient_matrix_UB_33      0.0682
_diffrn_orient_matrix_type       d*Trek

_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 for Windows ver 1.08 (Farrugia, 1997-2005)'
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0536P)^2^+0.0087P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3488
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.1216(2) 0.79266(17) 0.32797(18) 0.0195(4) Uani 1 1 d . . .
C1 C -0.05264(18) 0.74801(14) 0.24868(15) 0.0208(3) Uani 1 1 d . . .
C2 C -0.18181(18) 0.80293(16) 0.23544(16) 0.0246(4) Uani 1 1 d . . .
H1 H -0.1775 0.8838 0.2898 0.030 Uiso 1 1 calc R . .
C3 C -0.31799(19) 0.73936(18) 0.14228(17) 0.0290(4) Uani 1 1 d . . .
H2 H -0.4064 0.7775 0.1347 0.035 Uiso 1 1 calc R . .
C4 C -0.32922(19) 0.62148(17) 0.05946(17) 0.0307(4) Uani 1 1 d . . .
H3 H -0.4241 0.5811 -0.0047 0.037 Uiso 1 1 calc R .. .
C5 C -0.20088(19) 0.56292(16) 0.07093(16) 0.0274(4) Uani 1 1 d . . .
H4 H -0.2054 0.4820 0.0166 0.033 Uiso 1 1 calc R . .
C6 C -0.06568(17) 0.62870(15) 0.16590(15) 0.0211(3) Uani 1 1 d .. . .
N1 N 0.07037(15) 0.57967(12) 0.18396(13) 0.0231(3) Uani 1 1 d . . .
N2 N 0.17512(14) 0.66268(12) 0.26772(12) 0.0197(3) Uani 1 1 d . . .
C7 C 0.32491(17) 0.62816(15) 0.30785(15) 0.0212(3) Uani 1 1 d . . .
C8 C 0.35249(19) 0.50150(16) 0.29322(16) 0.0276(4) Uani 1 1 d . . .
H5 H 0.2727 0.4359 0.2562 0.033 Uiso 1 1 calc R . .
C9 C 0.4980(2) 0.47231(17) 0.33341(18) 0.0341(4) Uani 1 1 d . . .
H6 H 0.5183 0.3858 0.3236 0.041 Uiso 1 1 calc R . .
C10 C 0.6139(2) 0.56705(17) 0.38743(18) 0.0319(4) Uani 1 1 d . . .
H7 H 0.7134 0.5457 0.4148 0.038 Uiso 1 1 calc R .. .
C11 C 0.58604(18) 0.69290(17) 0.40193(17) 0.0278(4) Uani 1 1 d . . .
H8 H 0.6665 0.7579 0.4387 0.033 Uiso 1 1 calc R . .
C12 C 0.44057(18) 0.72519(15) 0.36296(16) 0.0240(4) Uani 1 1 d . . .
H9 H 0.4208 0.8117 0.3738 0.029 Uiso 1 1 calc R . .
C13 C 0.19741(17) 0.80540(14) 0.49451(15) 0.0194(3) Uani 1 1 d . . .
C14 C 0.15079(17) 0.71740(15) 0.55359(16) 0.0229(4) Uani 1 1 d .. . .
C15 C 0.21082(19) 0.71703(16) 0.69190(17) 0.0265(4) Uani 1 1 d . . .
C16 C 0.32364(19) 0.80766(18) 0.78034(16) 0.0293(4) Uani 1 1 d . . .
C17 C 0.37494(18) 0.89702(16) 0.72865(16) 0.0279(4) Uani 1 1 d . . .
C18 C 0.31275(17) 0.89338(15) 0.58810(16) 0.0221(4) Uani 1 1 d . . .
F1 F 0.04357(11) 0.62312(9) 0.47272(10) 0.0309(3) Uani 1 1 d .. . .
F2 F 0.16298(12) 0.62722(10) 0.74124(11) 0.0400(3) Uani 1 1 d . . .
F3 F 0.38615(12) 0.80676(11) 0.91497(10) 0.0451(3) Uani 1 1 d . . .
F4 F 0.48558(11) 0.98623(10) 0.81280(10) 0.0416(3) Uani 1 1 d . . .
F5 F 0.37345(10) 0.98199(9) 0.54539(10) 0.0298(2) Uani 1 1 d . . .
C19 C 0.15083(16) 0.91260(14) 0.26530(15) 0.0192(3) Uani 1 1 d .. . .
C20 C 0.12250(17) 1.03283(15) 0.31496(15) 0.0207(3) Uani 1 1 d . . .
C21 C 0.12825(17) 1.13779(14) 0.25909(16) 0.0224(4) Uani 1 1 d . . .
C22 C 0.15900(17) 1.12449(15) 0.14472(16) 0.0223(4) Uani 1 1 d . . .
C23 C 0.18376(17) 1.00697(15) 0.08856(15) 0.0214(4) Uani 1 1 d . . .
C24 C 0.17936(17) 0.90426(15) 0.14881(16) 0.0208(3) Uani 1 1 d .. . .
F6 F 0.08507(11) 1.05081(9) 0.42354(9) 0.0269(2) Uani 1 1 d . . .
F7 F 0.10196(11) 1.25197(8) 0.31378(10) 0.0305(2) Uani 1 1 d . . .
F8 F 0.16167(12) 1.22484(9) 0.08712(10) 0.0332(3) Uani 1 1 d . . .
F9 F 0.20860(11) 0.99218(9) -0.02580(9) 0.0297(2) Uani 1 1 d . . .
F10 F 0.20242(11) 0.79161(8) 0.08641(9) 0.0279(2) Uani 1 1 d . .. .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.0205(9) 0.0200(9) 0.0185(9) 0.0045(7) 0.0083(7) 0.0030(7)
C1 0.0253(8) 0.0229(8) 0.0159(7) 0.0095(6) 0.0081(7) -0.0002(6)
C2 0.0258(9) 0.0295(9) 0.0205(8) 0.0099(7) 0.0093(7) 0.0036(7)
C3 0.0235(9) 0.0424(10) 0.0255(9) 0.0163(8) 0.0106(7) 0.0052(7)
C4 0.0225(8) 0.0416(11) 0.0225(8) 0.0140(8) 0.0012(7) -0.0098(7)
C5 0.0346(9) 0.0253(9) 0.0199(8) 0.0071(7) 0.0082(7) -0.0067(7)
C6 0.0230(8) 0.0231(8) 0.0182(8) 0.0097(6) 0.0073(7) 0.0005(6)
N1 0.0277(7) 0.0211(7) 0.0190(7) 0.0054(6) 0.0076(6) -0.0012(6)
N2 0.0240(7) 0.0181(7) 0.0154(6) 0.0039(5) 0.0062(6) 0.0011(5)
C7 0.0212(8) 0.0283(9) 0.0161(7) 0.0070(6) 0.0086(7) 0.0069(7)
C8 0.0320(9) 0.0226(9) 0.0245(9) 0.0034(7) 0.0084(8) 0.0015(7)
C9 0.0400(10) 0.0265(9) 0.0344(10) 0.0049(8) 0.0139(9) 0.0155(8)
C10 0.0257(9) 0.0416(11) 0.0316(9) 0.0098(8) 0.0134(8) 0.0125(8)
C11 0.0236(9) 0.0343(9) 0.0239(8) 0.0052(7) 0.0086(7) 0.0002(7)
C12 0.0288(9) 0.0224(8) 0.0224(8) 0.0048(7) 0.0119(7) 0.0052(7)
C13 0.0206(8) 0.0197(8) 0.0185(8) 0.0042(6) 0.0083(7) 0.0052(6)
C14 0.0219(8) 0.0242(8) 0.0229(8) 0.0066(7) 0.0088(7) 0.0051(7)
C15 0.0306(9) 0.0335(9) 0.0242(9) 0.0163(7) 0.0154(8) 0.0163(7)
C16 0.0294(9) 0.0451(11) 0.0154(8) 0.0103(7) 0.0087(7) 0.0227(8)
C17 0.0206(8) 0.0333(9) 0.0213(8) -0.0029(7) 0.0031(7) 0.0095(7)
C18 0.0212(8) 0.0235(8) 0.0226(8) 0.0039(7) 0.0102(7) 0.0048(6)
F1 0.0356(6) 0.0271(5) 0.0284(5) 0.0112(4) 0.0097(5) -0.0062(4)
F2 0.0497(7) 0.0483(7) 0.0368(6) 0.0295(5) 0.0238(6) 0.0178(5)
F3 0.0460(7) 0.0699(8) 0.0159(5) 0.0135(5) 0.0061(5) 0.0286(6)
F4 0.0267(6) 0.0493(7) 0.0278(6) -0.0106(5) -0.0026(5) 0.0013(5)
F5 0.0267(5) 0.0272(5) 0.0302(5) 0.0002(4) 0.0088(4) -0.0061(4)
C19 0.0182(8) 0.0207(8) 0.0169(7) 0.0051(6) 0.0049(6) -0.0010(6)
C20 0.0190(8) 0.0255(8) 0.0162(7) 0.0028(6) 0.0066(6) 0.0005(6)
C21 0.0214(8) 0.0185(8) 0.0235(8) 0.0034(6) 0.0057(7) 0.0020(6)
C22 0.0211(8) 0.0219(8) 0.0226(8) 0.0114(7) 0.0050(7) -0.0012(6)
C23 0.0190(8) 0.0306(9) 0.0154(8) 0.0078(7) 0.0067(7) -0.0001(7)
C24 0.0203(8) 0.0206(8) 0.0191(8) 0.0019(6) 0.0066(7) 0.0007(6)
F6 0.0359(6) 0.0259(5) 0.0243(5) 0.0050(4) 0.0178(4) 0.0055(4)
F7 0.0381(6) 0.0199(5) 0.0336(6) 0.0048(4) 0.0147(5) 0.0076(4)
F8 0.0455(6) 0.0249(5) 0.0310(6) 0.0142(4) 0.0142(5) 0.0022(4)
F9 0.0377(6) 0.0357(6) 0.0219(5) 0.0111(4) 0.0164(5) 0.0037(4)
F10 0.0424(6) 0.0224(5) 0.0233(5) 0.0040(4) 0.0182(5) 0.0059(4)

_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 C1 1.599(2) . ?
B1 N2 1.625(2) . ?
B1 C19 1.627(2) . ?
B1 C13 1.629(2) . ?
C1 C2 1.379(2) . ?
C1 C6 1.401(2) . ?
C2 C3 1.386(2) . ?
C2 H1 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H2 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H3 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H4 0.9500 . ?
C6 N1 1.402(2) . ?
N1 N2 1.2704(18) . ?
N2 C7 1.438(2) . ?
C7 C8 1.386(2) . ?
C7 C12 1.390(2) . ?
C8 C9 1.382(3) . ?
C8 H5 0.9500 . ?
C9 C10 1.376(3) . ?
C9 H6 0.9500 . ?
C10 C11 1.378(3) . ?
C10 H7 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H8 0.9500 . ?
C12 H9 0.9500 . ?
C13 C18 1.383(2) . ?
C13 C14 1.393(2) . ?
C14 F1 1.3473(19) . ?
C14 C15 1.371(2) . ?
C15 F2 1.342(2) . ?
C15 C16 1.371(3) . ?
C16 F3 1.336(2) . ?
C16 C17 1.372(3) . ?
C17 F4 1.340(2) . ?
C17 C18 1.385(2) . ?
C18 F5 1.3525(19) . ?
C19 C24 1.387(2) . ?
C19 C20 1.388(2) . ?
C20 F6 1.3518(19) . ?
C20 C21 1.378(2) . ?
C21 F7 1.3430(18) . ?
C21 C22 1.374(2) . ?
C22 F8 1.3394(18) . ?
C22 C23 1.373(2) . ?
C23 F9 1.3395(18) . ?
C23 C24 1.383(2) . ?
C24 F10 1.3493(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
C1 B1 N2 95.53(12) . . ?
C1 B1 C19 106.04(13) . .. ?
N2 B1 C19 112.35(13) . . ?
C1 B1 C13 117.74(13) . . ?
N2 B1 C13 105.07(12) . . ?
C19 B1 C13 117.93(13) . . ?
C2 C1 C6 117.74(15) . . ?
C2 C1 B1 135.52(15) . . ?
C6 C1 B1 106.37(14) . . ?
C1 C2 C3 119.56(16) . . ?
C1 C2 H1 120.2 . . ?
C3 C2 H1 120.2 . . ?
C2 C3 C4 122.09(16) . .. ?
C2 C3 H2 119.0 . . ?
C4 C3 H2 119.0 . . ?
C3 C4 C5 119.81(16) . . ?
C3 C4 H3 120.1 . . ?
C5 C4 H3 120.1 . . ?
C6 C5 C4 116.84(16) . . ?
C6 C5 H4 121.6 . . ?
C4 C5 H4 121.6 . . ?
C5 C6 C1 123.95(15) . . ?
C5 C6 N1 121.58(15) . .. ?
C1 C6 N1 114.45(14) . . ?
N2 N1 C6 108.45(13) . . ?
N1 N2 C7 117.50(13) . . ?
N1 N2 B1 114.97(13) . . ?
C7 N2 B1 127.28(12) . . ?
C8 C7 C12 121.23(15) . . ?
C8 C7 N2 120.64(14) . . ?
C12 C7 N2 118.13(14) . . ?
C9 C8 C7 118.86(16) . . ?
C9 C8 H5 120.6 . . ?
C7 C8 H5 120.6 . . ?
C10 C9 C8 120.74(16) . . ?
C10 C9 H6 119.6 . . ?
C8 C9 H6 119.6 . . ?
C9 C10 C11 120.23(16) . . ?
C9 C10 H7 119.9 . . ?
C11 C10 H7 119.9 . . ?
C10 C11 C12 120.30(16) . . ?
C10 C11 H8 119.9 . . ?
C12 C11 H8 119.9 . . ?
C7 C12 C11 118.64(15) .. . ?
C7 C12 H9 120.7 . . ?
C11 C12 H9 120.7 . . ?
C18 C13 C14 113.94(15) . . ?
C18 C13 B1 126.54(14) . . ?
C14 C13 B1 119.43(14) . . ?
F1 C14 C15 116.13(15) . . ?
F1 C14 C13 119.80(14) . . ?
C15 C14 C13 124.04(16) . . ?
F2 C15 C16 119.63(15) . . ?
F2 C15 C14 120.80(16) . . ?
C16 C15 C14 119.56(16) . . ?
F3 C16 C15 120.38(17) . . ?
F3 C16 C17 120.28(17) . . ?
C15 C16 C17 119.31(16) . . ?
F4 C17 C16 120.49(16) . . ?
F4 C17 C18 120.04(17) . . ?
C16 C17 C18 119.47(16) . . ?
F5 C18 C13 120.71(15) . . ?
F5 C18 C17 115.62(15) . . ?
C13 C18 C17 123.67(16) . . ?
C24 C19 C20 114.27(14) . . ?
C24 C19 B1 125.44(14) . . ?
C20 C19 B1 119.42(14) . . ?
F6 C20 C21 116.52(14) . . ?
F6 C20 C19 119.54(14) . . ?
C21 C20 C19 123.94(15) . . ?
F7 C21 C22 119.84(14) . . ?
F7 C21 C20 120.84(15) . . ?
C22 C21 C20 119.32(15) . . ?
F8 C22 C23 120.48(15) . . ?
F8 C22 C21 120.16(15) . . ?
C23 C22 C21 119.35(14) . . ?
F9 C23 C22 119.77(14) . . ?
F9 C23 C24 120.56(14) . . ?
C22 C23 C24 119.65(15) . . ?
F10 C24 C23 116.16(14) . . ?
F10 C24 C19 120.42(14) . . ?
C23 C24 C19 123.41(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
N2 B1 C1 C2 -176.29(17) . . . . ?
C19 B1 C1 C2 -61.1(2) . . . . ?
C13 B1 C1 C2 73.5(2) . . . . ?
N2 B1 C1 C6 -3.63(14) . .. . . ?
C19 B1 C1 C6 111.55(14) . . . . ?
C13 B1 C1 C6 -113.87(15) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
B1 C1 C2 C3 172.06(16) . . . . ?
C1 C2 C3 C4 -0.8(2) . .. . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 N1 -178.80(13) .. . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
B1 C1 C6 C5 -173.86(14) . . . . ?
C2 C1 C6 N1 179.29(13) . . . . ?
B1 C1 C6 N1 5.09(17) . . . . ?
C5 C6 N1 N2 174.79(14) . .. . . ?
C1 C6 N1 N2 -4.19(17) . . . . ?
C6 N1 N2 C7 175.96(12) . . . . ?
C6 N1 N2 B1 1.30(17) . . . . ?
C1 B1 N2 N1 1.48(16) . . . . ?
C19 B1 N2 N1 -108.39(15) .. . . . ?
C13 B1 N2 N1 122.17(13) . . . .. ?
C1 B1 N2 C7 -172.56(13) . . . . ?
C19 B1 N2 C7 77.56(18) . . . . ?
C13 B1 N2 C7 -51.88(19) . . . . ?
N1 N2 C7 C8 -20.2(2) .. . . . ?
B1 N2 C7 C8 153.69(15) . . . . ?
N1 N2 C7 C12 160.52(14) . . . . ?
B1 N2 C7 C12 -25.6(2) . . . . ?
C12 C7 C8 C9 -0.6(2) . . . . ?
N2 C7 C8 C9 -179.79(14) . .. . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C8 C7 C12 C11 0.9(2) . . . . ?
N2 C7 C12 C11 -179.88(13) . .. . . ?
C10 C11 C12 C7 -0.8(2) . . . . ?
C1 B1 C13 C18 -146.05(15) . . . . ?
N2 B1 C13 C18 109.22(17) . . . . ?
C19 B1 C13 C18 -16.8(2) . . . . ?
C1 B1 C13 C14 37.5(2) .. . . . ?
N2 B1 C13 C14 -67.27(18) . . . .. ?
C19 B1 C13 C14 166.68(14) . . . . ?
C18 C13 C14 F1 -177.06(13) . . . . ?
B1 C13 C14 F1 -0.1(2) . . . . ?
C18 C13 C14 C15 0.8(2) . . . . ?
B1 C13 C14 C15 177.67(14) . . . . ?
F1 C14 C15 F2 -0.3(2) . .. . . ?
C13 C14 C15 F2 -178.23(13) . . . . ?
F1 C14 C15 C16 178.02(13) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
F2 C15 C16 F3 0.2(2) . . . . ?
C14 C15 C16 F3 -178.23(14) . . . . ?
F2 C15 C16 C17 178.12(14) . . . . ?
C14 C15 C16 C17 -0.3(2) .. . . . ?
F3 C16 C17 F4 -1.7(2) . . . . ?
C15 C16 C17 F4 -179.66(14) . . . . ?
F3 C16 C17 C18 177.43(13) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C14 C13 C18 F5 177.61(13) . . . . ?
B1 C13 C18 F5 0.9(2) . .. . . ?
C14 C13 C18 C17 -1.6(2) . . . . ?
B1 C13 C18 C17 -178.26(14) . . . . ?
F4 C17 C18 F5 1.4(2) . . . . ?
C16 C17 C18 F5 -177.68(13) . . . . ?
F4 C17 C18 C13 -179.32(14) . . . . ?
C16 C17 C18 C13 1.6(2) .. . . . ?
C1 B1 C19 C24 -86.54(18) . . . .. ?
N2 B1 C19 C24 16.6(2) . . . . ?
C13 B1 C19 C24 138.98(16) . . . . ?
C1 B1 C19 C20 82.16(18) . . . . ?
N2 B1 C19 C20 -174.74(13) . . . . ?
C13 B1 C19 C20 -52.3(2) .. . . . ?
C24 C19 C20 F6 176.34(12) . . . .. ?
B1 C19 C20 F6 6.4(2) . . . . ?
C24 C19 C20 C21 -2.9(2) . . . . ?
B1 C19 C20 C21 -172.78(14) . . . . ?
F6 C20 C21 F7 1.9(2) . . . . ?
C19 C20 C21 F7 -178.88(14) .. . . . ?
F6 C20 C21 C22 -177.07(13) . . . .. ?
C19 C20 C21 C22 2.2(2) . . . . ?
F7 C21 C22 F8 -0.5(2) . . . . ?
C20 C21 C22 F8 178.46(13) . . . . ?
F7 C21 C22 C23 -179.14(14) . . . . ?
C20 C21 C22 C23 -0.2(2) .. . . . ?
F8 C22 C23 F9 -1.0(2) . . . . ?
C21 C22 C23 F9 177.64(13) . . . . ?
F8 C22 C23 C24 -179.47(13) . . . . ?
C21 C22 C23 C24 -0.9(2) . . . . ?
F9 C23 C24 F10 0.5(2) . . . . ?
C22 C23 C24 F10 178.97(13) .. . . . ?
F9 C23 C24 C19 -178.49(13) . . . .. ?
C22 C23 C24 C19 0.0(2) . . . . ?
C20 C19 C24 F10 -177.17(13) . . . . ?
B1 C19 C24 F10 -8.0(2) . . . . ?
C20 C19 C24 C23 1.8(2) . . . . ?
B1 C19 C24 C23 170.98(14) . .. . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053