#------------------------------------------------------------------------------
#$Date: 2018-04-16 18:06:05 +0300 (Mon, 16 Apr 2018) $
#$Revision: 207363 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/04/7230476.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7230476
loop_
_publ_author_name
'Uno, Hidemitsu'
'Honda, Takayuki'
'Kitatsuka, Manami'
'Hiraoka, Shogo'
'Mori, Shigeki'
'Takase, Masayoshi'
'Okujima, Tetsuo'
'Nakae, Takahiro'
_publ_section_title
;
 Benzene-fused bis(acenaphthoBODIPY)s, stable near-infrared-selective dyes
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              14072
_journal_paper_doi               10.1039/C8RA01694A
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C88 H100 B2 F4 N4'
_chemical_formula_sum            'C88 H100 B2 F4 N4'
_chemical_formula_weight         1311.40
_chemical_name_systematic        B-bisANBODIPYMe4
_chemical_properties_physical    Deliquescent
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-02-05 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.513(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   40.901(3)
_cell_length_b                   9.5734(8)
_cell_length_c                   23.3784(19)
_cell_measurement_reflns_used    6852
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.52
_cell_volume                     8628.3(13)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            46544
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.194
_diffrn_reflns_theta_min         3.900
_exptl_absorpt_coefficient_mu    0.498
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.010
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3480.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/hexane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     498
_refine_ls_number_reflns         7788
_refine_ls_number_restraints     276
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0965P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.1870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4786
_reflns_number_total             7788
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c8ra01694a3.cif
_cod_data_source_block           290727_4
_cod_original_cell_volume        8628.3(12)
_cod_database_code               7230476
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'
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 0.54884(3) 0.21181(14) 0.73151(5) 0.0646(4) Uani 1 1 d . . . . .
F2 F 0.58831(3) 0.04128(13) 0.73737(5) 0.0646(4) Uani 1 1 d . . . . .
N1 N 0.54909(5) 0.10435(19) 0.63881(7) 0.0505(5) Uani 1 1 d . . . . .
N2 N 0.59717(5) 0.2621(2) 0.69686(8) 0.0547(5) Uani 1 1 d . . . . .
C1 C 0.52284(6) 0.0127(2) 0.62620(9) 0.0522(6) Uani 1 1 d . . . . .
C2 C 0.50863(6) -0.0060(2) 0.56144(9) 0.0509(6) Uani 1 1 d . . . . .
C3 C 0.52793(6) 0.0827(2) 0.53507(9) 0.0504(6) Uani 1 1 d . . . . .
C4 C 0.55353(6) 0.1529(2) 0.58475(9) 0.0496(6) Uani 1 1 d . . . . .
C5 C 0.57884(6) 0.2505(2) 0.58634(9) 0.0488(6) Uani 1 1 d . . . . .
C6 C 0.60123(6) 0.3046(2) 0.64152(9) 0.0503(6) Uani 1 1 d . . . . .
C7 C 0.62926(6) 0.3987(2) 0.65594(9) 0.0513(6) Uani 1 1 d . . . . .
C8 C 0.64151(6) 0.4112(2) 0.72027(10) 0.0561(6) Uani 1 1 d . . . . .
C9 C 0.62144(6) 0.3295(3) 0.74410(10) 0.0586(6) Uani 1 1 d . . . . .
C10 C 0.51892(6) 0.0890(2) 0.47203(9) 0.0512(6) Uani 1 1 d . . . . .
H10 H 0.531049 0.147229 0.453004 0.061 Uiso 1 1 calc R U . . .
C11 C 0.65067(6) 0.4889(2) 0.63162(10) 0.0517(6) Uani 1 1 d . . . . .
C12 C 0.65241(6) 0.5250(2) 0.57529(10) 0.0543(6) Uani 1 1 d . . . . .
H12 H 0.636270 0.486489 0.539506 0.065 Uiso 1 1 calc R U . . .
C13 C 0.67833(6) 0.6198(3) 0.57090(10) 0.0575(6) Uani 1 1 d . . . . .
C14 C 0.70184(7) 0.6766(3) 0.62278(10) 0.0603(6) Uani 1 1 d . . . . .
H14 H 0.718812 0.740134 0.618883 0.072 Uiso 1 1 calc R U . . .
C15 C 0.70144(6) 0.6432(2) 0.68145(10) 0.0553(6) Uani 1 1 d . . . . .
C16 C 0.67504(6) 0.5513(2) 0.68353(10) 0.0528(6) Uani 1 1 d . . . . .
C17 C 0.67154(6) 0.5071(2) 0.73882(10) 0.0556(6) Uani 1 1 d . . . . .
C18 C 0.69426(7) 0.5551(2) 0.79229(10) 0.0591(6) Uani 1 1 d . . . . .
H18 H 0.691998 0.525799 0.829609 0.071 Uiso 1 1 calc R U . . .
C19 C 0.72153(6) 0.6496(3) 0.79257(10) 0.0586(6) Uani 1 1 d . . . . .
C20 C 0.72456(6) 0.6920(2) 0.73802(10) 0.0586(6) Uani 1 1 d . . . . .
H20 H 0.742521 0.755197 0.738303 0.070 Uiso 1 1 calc R U . . .
C21 C 0.51072(7) -0.0540(3) 0.67307(10) 0.0626(7) Uani 1 1 d . . . . .
H21A H 0.491319 -0.116870 0.653340 0.094 Uiso 0.5 1 calc R U P . .
H21B H 0.529777 -0.107348 0.701285 0.094 Uiso 0.5 1 calc R U P . .
H21C H 0.503078 0.018419 0.695434 0.094 Uiso 0.5 1 calc R U P . .
H21D H 0.524797 -0.020330 0.713366 0.094 Uiso 0.5 1 calc R U P . .
H21E H 0.486339 -0.029852 0.665421 0.094 Uiso 0.5 1 calc R U P . .
H21F H 0.513038 -0.155619 0.671272 0.094 Uiso 0.5 1 calc R U P . .
C22 C 0.62323(7) 0.3143(3) 0.80804(10) 0.0726(8) Uani 1 1 d . . . . .
H22A H 0.642357 0.371082 0.834098 0.109 Uiso 0.5 1 calc R U P . .
H22B H 0.601350 0.345623 0.812277 0.109 Uiso 0.5 1 calc R U P . .
H22C H 0.627185 0.215985 0.820113 0.109 Uiso 0.5 1 calc R U P . .
H22D H 0.604904 0.250711 0.810228 0.109 Uiso 0.5 1 calc R U P . .
H22E H 0.645911 0.276170 0.832048 0.109 Uiso 0.5 1 calc R U P . .
H22F H 0.620076 0.405808 0.824212 0.109 Uiso 0.5 1 calc R U P . .
C23 C 0.58151(6) 0.2980(2) 0.52717(9) 0.0489(5) Uani 1 1 d . . . . .
C24 C 0.56148(6) 0.4111(2) 0.49742(10) 0.0523(6) Uani 1 1 d . . . . .
H24 H 0.548769 0.463842 0.517292 0.063 Uiso 1 1 calc R U . . .
C25 C 0.55994(6) 0.4476(2) 0.43893(10) 0.0529(6) Uani 1 1 d . . . . .
C26 C 0.57965(6) 0.3703(2) 0.41207(10) 0.0548(6) Uani 1 1 d . . . . .
H26 H 0.578963 0.395226 0.372347 0.066 Uiso 1 1 calc R U . . .
C27 C 0.60042(6) 0.2578(2) 0.44068(9) 0.0535(6) Uani 1 1 d . . . . .
C28 C 0.60073(6) 0.2222(2) 0.49880(10) 0.0524(6) Uani 1 1 d . . . . .
H28 H 0.614260 0.145055 0.519218 0.063 Uiso 1 1 calc R U . . .
C29 C 0.53539(8) 0.5656(3) 0.40474(12) 0.0732(8) Uani 1 1 d D U . . .
C30 C 0.49727(16) 0.5103(8) 0.3886(4) 0.100(2) Uani 0.636(8) 1 d D U P A 1
H30A H 0.480992 0.587998 0.374010 0.151 Uiso 0.636(8) 1 calc R U P A 1
H30B H 0.494127 0.469411 0.424797 0.151 Uiso 0.636(8) 1 calc R U P A 1
H30C H 0.492880 0.439114 0.356779 0.151 Uiso 0.636(8) 1 calc R U P A 1
C31 C 0.54217(19) 0.6196(8) 0.3508(3) 0.100(3) Uani 0.636(8) 1 d D U P A 1
H31A H 0.565465 0.660396 0.363012 0.150 Uiso 0.636(8) 1 calc R U P A 1
H31B H 0.524963 0.691281 0.331268 0.150 Uiso 0.636(8) 1 calc R U P A 1
H31C H 0.540596 0.542938 0.322202 0.150 Uiso 0.636(8) 1 calc R U P A 1
C32 C 0.53929(17) 0.6916(5) 0.4499(3) 0.101(2) Uani 0.636(8) 1 d D U P A 1
H32A H 0.563776 0.718314 0.466902 0.152 Uiso 0.636(8) 1 calc R U P A 1
H32B H 0.530808 0.663772 0.482728 0.152 Uiso 0.636(8) 1 calc R U P A 1
H32C H 0.525718 0.771220 0.427991 0.152 Uiso 0.636(8) 1 calc R U P A 1
C130 C 0.5543(2) 0.7020(7) 0.4136(5) 0.089(4) Uani 0.364(8) 1 d D U P A 2
H13A H 0.538022 0.776831 0.394193 0.133 Uiso 0.364(8) 1 calc R U P A 2
H13B H 0.572627 0.697162 0.395309 0.133 Uiso 0.364(8) 1 calc R U P A 2
H13C H 0.564669 0.721455 0.457101 0.133 Uiso 0.364(8) 1 calc R U P A 2
C131 C 0.5031(3) 0.5705(12) 0.4202(5) 0.071(3) Uani 0.364(8) 1 d D U P A 2
H13D H 0.507819 0.616657 0.459572 0.106 Uiso 0.364(8) 1 calc R U P A 2
H13E H 0.494918 0.475138 0.422455 0.106 Uiso 0.364(8) 1 calc R U P A 2
H13F H 0.485355 0.622815 0.388936 0.106 Uiso 0.364(8) 1 calc R U P A 2
C132 C 0.5242(3) 0.5363(12) 0.3328(3) 0.081(3) Uani 0.364(8) 1 d D U P A 2
H13G H 0.510485 0.450234 0.322891 0.121 Uiso 0.364(8) 1 calc R U P A 2
H13H H 0.545038 0.526120 0.321320 0.121 Uiso 0.364(8) 1 calc R U P A 2
H13I H 0.510305 0.614686 0.310510 0.121 Uiso 0.364(8) 1 calc R U P A 2
C33 C 0.61944(7) 0.1652(3) 0.40739(10) 0.0638(7) Uani 1 1 d . . . . .
C34 C 0.65502(7) 0.1221(3) 0.45054(11) 0.0715(7) Uani 1 1 d . . . . .
H34A H 0.668693 0.205752 0.467177 0.107 Uiso 1 1 calc R U . . .
H34B H 0.667020 0.066497 0.428431 0.107 Uiso 1 1 calc R U . . .
H34C H 0.652225 0.066268 0.483745 0.107 Uiso 1 1 calc R U . . .
C35 C 0.59616(8) 0.0355(3) 0.38450(13) 0.0862(9) Uani 1 1 d . . . . .
H35A H 0.594131 -0.016501 0.419276 0.129 Uiso 1 1 calc R U . . .
H35B H 0.606534 -0.024736 0.361284 0.129 Uiso 1 1 calc R U . . .
H35C H 0.573085 0.065459 0.358449 0.129 Uiso 1 1 calc R U . . .
C36 C 0.62426(8) 0.2385(3) 0.35254(12) 0.0819(9) Uani 1 1 d . . . . .
H36A H 0.601550 0.254272 0.321597 0.123 Uiso 1 1 calc R U . . .
H36B H 0.638426 0.179724 0.335650 0.123 Uiso 1 1 calc R U . . .
H36C H 0.635908 0.328301 0.365273 0.123 Uiso 1 1 calc R U . . .
C37 C 0.67910(7) 0.6575(3) 0.50758(11) 0.0684(7) Uani 1 1 d . . . . .
C38 C 0.68406(10) 0.5276(3) 0.47506(13) 0.1040(11) Uani 1 1 d . . . . .
H38A H 0.681365 0.550668 0.432879 0.156 Uiso 1 1 calc R U . . .
H38B H 0.666698 0.457780 0.475825 0.156 Uiso 1 1 calc R U . . .
H38C H 0.707351 0.489947 0.495302 0.156 Uiso 1 1 calc R U . . .
C39 C 0.64273(8) 0.7190(3) 0.47087(11) 0.0825(9) Uani 1 1 d . . . . .
H39A H 0.636837 0.793606 0.494456 0.124 Uiso 1 1 calc R U . . .
H39B H 0.625217 0.645038 0.462817 0.124 Uiso 1 1 calc R U . . .
H39C H 0.643333 0.757087 0.432316 0.124 Uiso 1 1 calc R U . . .
C40 C 0.70484(9) 0.7699(3) 0.50853(13) 0.0962(10) Uani 1 1 d . . . . .
H40A H 0.699401 0.854173 0.527397 0.144 Uiso 1 1 calc R U . . .
H40B H 0.703687 0.791147 0.466895 0.144 Uiso 1 1 calc R U . . .
H40C H 0.728249 0.737802 0.531925 0.144 Uiso 1 1 calc R U . . .
C41 C 0.74692(7) 0.6969(3) 0.85390(11) 0.0664(7) Uani 1 1 d D U . . .
C42 C 0.72723(9) 0.7645(4) 0.89199(14) 0.0716(11) Uani 0.825(5) 1 d D U P B 1
H42A H 0.714117 0.845113 0.870168 0.107 Uiso 0.825(5) 1 calc R U P B 1
H42B H 0.743767 0.795422 0.930868 0.107 Uiso 0.825(5) 1 calc R U P B 1
H42C H 0.711200 0.696369 0.899328 0.107 Uiso 0.825(5) 1 calc R U P B 1
C43 C 0.77387(9) 0.7983(4) 0.84725(16) 0.0734(11) Uani 0.825(5) 1 d D U P B 1
H43A H 0.788682 0.750803 0.827928 0.110 Uiso 0.825(5) 1 calc R U P B 1
H43B H 0.788119 0.832043 0.887418 0.110 Uiso 0.825(5) 1 calc R U P B 1
H43C H 0.762239 0.877497 0.822114 0.110 Uiso 0.825(5) 1 calc R U P B 1
C44 C 0.76557(9) 0.5662(4) 0.88731(16) 0.0789(12) Uani 0.825(5) 1 d D U P B 1
H44A H 0.748725 0.504504 0.896110 0.118 Uiso 0.825(5) 1 calc R U P B 1
H44B H 0.783361 0.593950 0.925411 0.118 Uiso 0.825(5) 1 calc R U P B 1
H44C H 0.776512 0.516794 0.861742 0.118 Uiso 0.825(5) 1 calc R U P B 1
C142 C 0.7866(4) 0.668(3) 0.8582(9) 0.135(8) Uani 0.175(5) 1 d D U P B 2
H14E H 0.802055 0.685145 0.899675 0.202 Uiso 0.175(5) 1 calc R U P B 2
H14F H 0.792817 0.729664 0.830078 0.202 Uiso 0.175(5) 1 calc R U P B 2
H14G H 0.788962 0.570146 0.847279 0.202 Uiso 0.175(5) 1 calc R U P B 2
C143 C 0.7455(7) 0.650(2) 0.9137(8) 0.122(8) Uani 0.175(5) 1 d D U P B 2
H14H H 0.723436 0.678753 0.917824 0.183 Uiso 0.175(5) 1 calc R U P B 2
H14I H 0.764726 0.692390 0.946274 0.183 Uiso 0.175(5) 1 calc R U P B 2
H14J H 0.747560 0.548052 0.916468 0.183 Uiso 0.175(5) 1 calc R U P B 2
C144 C 0.7437(7) 0.8595(14) 0.8562(9) 0.145(10) Uani 0.175(5) 1 d D U P B 2
H14K H 0.722099 0.883839 0.863289 0.218 Uiso 0.175(5) 1 calc R U P B 2
H14L H 0.743521 0.899645 0.817532 0.218 Uiso 0.175(5) 1 calc R U P B 2
H14M H 0.763471 0.896854 0.889209 0.218 Uiso 0.175(5) 1 calc R U P B 2
B1 B 0.57092(8) 0.1552(3) 0.70360(11) 0.0527(7) Uani 1 1 d . . . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C1 N1 C4 110.55(17) .
C1 N1 B1 125.10(18) .
C4 N1 B1 124.32(19) .
C9 N2 C6 108.98(19) .
C9 N2 B1 125.10(18) .
C6 N2 B1 125.89(18) .
N1 C1 C2 108.96(19) .
N1 C1 C21 123.90(19) .
C2 C1 C21 127.1(2) .
C10 C2 C3 123.88(19) 5_656
C10 C2 C1 129.1(2) 5_656
C3 C2 C1 107.0(2) .
C10 C3 C2 119.4(2) .
C10 C3 C4 133.9(2) .
C2 C3 C4 106.61(18) .
C5 C4 N1 121.01(19) .
C5 C4 C3 132.09(19) .
N1 C4 C3 106.90(19) .
C4 C5 C6 121.61(19) .
C4 C5 C23 117.72(19) .
C6 C5 C23 120.7(2) .
C7 C6 C5 133.11(19) .
C7 C6 N2 107.41(18) .
C5 C6 N2 119.5(2) .
C6 C7 C8 106.16(19) .
C6 C7 C11 145.55(19) .
C8 C7 C11 108.3(2) .
C9 C8 C7 109.4(2) .
C9 C8 C17 141.5(2) .
C7 C8 C17 109.11(19) .
N2 C9 C8 108.0(2) .
N2 C9 C22 123.0(2) .
C8 C9 C22 129.0(2) .
C2 C10 C3 116.7(2) 5_656
C2 C10 H10 121.7 5_656
C3 C10 H10 121.7 .
C12 C11 C16 117.6(2) .
C12 C11 C7 137.6(2) .
C16 C11 C7 104.77(19) .
C11 C12 C13 120.2(2) .
C11 C12 H12 119.9 .
C13 C12 H12 119.9 .
C14 C13 C12 120.2(2) .
C14 C13 C37 121.5(2) .
C12 C13 C37 118.3(2) .
C13 C14 C15 122.2(2) .
C13 C14 H14 118.9 .
C15 C14 H14 118.9 .
C16 C15 C14 115.7(2) .
C16 C15 C20 116.9(2) .
C14 C15 C20 127.4(2) .
C15 C16 C17 122.2(2) .
C15 C16 C11 124.2(2) .
C17 C16 C11 113.5(2) .
C18 C17 C16 119.4(2) .
C18 C17 C8 136.3(2) .
C16 C17 C8 104.24(19) .
C17 C18 C19 120.5(2) .
C17 C18 H18 119.8 .
C19 C18 H18 119.8 .
C20 C19 C18 119.3(2) .
C20 C19 C41 122.4(2) .
C18 C19 C41 118.3(2) .
C19 C20 C15 121.6(2) .
C19 C20 H20 119.2 .
C15 C20 H20 119.2 .
C1 C21 H21A 109.5 .
C1 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C1 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C1 C21 H21D 109.5 .
H21A C21 H21D 141.1 .
H21B C21 H21D 56.3 .
H21C C21 H21D 56.3 .
C1 C21 H21E 109.5 .
H21A C21 H21E 56.3 .
H21B C21 H21E 141.1 .
H21C C21 H21E 56.3 .
H21D C21 H21E 109.5 .
C1 C21 H21F 109.5 .
H21A C21 H21F 56.3 .
H21B C21 H21F 56.3 .
H21C C21 H21F 141.1 .
H21D C21 H21F 109.5 .
H21E C21 H21F 109.5 .
C9 C22 H22A 109.5 .
C9 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C9 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C9 C22 H22D 109.5 .
H22A C22 H22D 141.1 .
H22B C22 H22D 56.3 .
H22C C22 H22D 56.3 .
C9 C22 H22E 109.5 .
H22A C22 H22E 56.3 .
H22B C22 H22E 141.1 .
H22C C22 H22E 56.3 .
H22D C22 H22E 109.5 .
C9 C22 H22F 109.5 .
H22A C22 H22F 56.3 .
H22B C22 H22F 56.3 .
H22C C22 H22F 141.1 .
H22D C22 H22F 109.5 .
H22E C22 H22F 109.5 .
C28 C23 C24 119.9(2) .
C28 C23 C5 120.71(19) .
C24 C23 C5 119.03(19) .
C25 C24 C23 120.7(2) .
C25 C24 H24 119.6 .
C23 C24 H24 119.6 .
C26 C25 C24 117.9(2) .
C26 C25 C29 122.0(2) .
C24 C25 C29 120.0(2) .
C25 C26 C27 123.1(2) .
C25 C26 H26 118.4 .
C27 C26 H26 118.4 .
C26 C27 C28 117.4(2) .
C26 C27 C33 121.87(19) .
C28 C27 C33 120.4(2) .
C23 C28 C27 120.9(2) .
C23 C28 H28 119.6 .
C27 C28 H28 119.6 .
C131 C29 C130 113.6(6) .
C31 C29 C25 115.1(3) .
C131 C29 C25 112.0(4) .
C130 C29 C25 110.5(4) .
C31 C29 C30 111.6(4) .
C25 C29 C30 107.5(3) .
C31 C29 C32 107.4(4) .
C25 C29 C32 108.1(3) .
C30 C29 C32 106.9(4) .
C131 C29 C132 107.2(5) .
C130 C29 C132 104.4(6) .
C25 C29 C132 108.7(4) .
C29 C30 H30A 109.5 .
C29 C30 H30B 109.5 .
H30A C30 H30B 109.5 .
C29 C30 H30C 109.5 .
H30A C30 H30C 109.5 .
H30B C30 H30C 109.5 .
C29 C31 H31A 109.5 .
C29 C31 H31B 109.5 .
H31A C31 H31B 109.5 .
C29 C31 H31C 109.5 .
H31A C31 H31C 109.5 .
H31B C31 H31C 109.5 .
C29 C32 H32A 109.5 .
C29 C32 H32B 109.5 .
H32A C32 H32B 109.5 .
C29 C32 H32C 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
C29 C130 H13A 109.5 .
C29 C130 H13B 109.5 .
H13A C130 H13B 109.5 .
C29 C130 H13C 109.5 .
H13A C130 H13C 109.5 .
H13B C130 H13C 109.5 .
C29 C131 H13D 109.5 .
C29 C131 H13E 109.5 .
H13D C131 H13E 109.5 .
C29 C131 H13F 109.5 .
H13D C131 H13F 109.5 .
H13E C131 H13F 109.5 .
C29 C132 H13G 109.5 .
C29 C132 H13H 109.5 .
H13G C132 H13H 109.5 .
C29 C132 H13I 109.5 .
H13G C132 H13I 109.5 .
H13H C132 H13I 109.5 .
C34 C33 C36 108.4(2) .
C34 C33 C35 110.7(2) .
C36 C33 C35 108.3(2) .
C34 C33 C27 110.53(19) .
C36 C33 C27 112.64(19) .
C35 C33 C27 106.2(2) .
C33 C34 H34A 109.5 .
C33 C34 H34B 109.5 .
H34A C34 H34B 109.5 .
C33 C34 H34C 109.5 .
H34A C34 H34C 109.5 .
H34B C34 H34C 109.5 .
C33 C35 H35A 109.5 .
C33 C35 H35B 109.5 .
H35A C35 H35B 109.5 .
C33 C35 H35C 109.5 .
H35A C35 H35C 109.5 .
H35B C35 H35C 109.5 .
C33 C36 H36A 109.5 .
C33 C36 H36B 109.5 .
H36A C36 H36B 109.5 .
C33 C36 H36C 109.5 .
H36A C36 H36C 109.5 .
H36B C36 H36C 109.5 .
C40 C37 C38 112.8(3) .
C40 C37 C13 113.2(2) .
C38 C37 C13 110.0(2) .
C40 C37 C39 105.8(2) .
C38 C37 C39 107.3(2) .
C13 C37 C39 107.2(2) .
C37 C38 H38A 109.5 .
C37 C38 H38B 109.5 .
H38A C38 H38B 109.5 .
C37 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 .
C37 C40 H40A 109.5 .
C37 C40 H40B 109.5 .
H40A C40 H40B 109.5 .
C37 C40 H40C 109.5 .
H40A C40 H40C 109.5 .
H40B C40 H40C 109.5 .
C43 C41 C42 109.3(2) .
C143 C41 C19 124.4(9) .
C43 C41 C19 112.5(2) .
C42 C41 C19 110.2(2) .
C43 C41 C44 108.6(3) .
C42 C41 C44 108.5(3) .
C19 C41 C44 107.6(2) .
C143 C41 C144 103.8(12) .
C19 C41 C144 106.7(8) .
C143 C41 C142 104.0(12) .
C19 C41 C142 111.1(8) .
C144 C41 C142 105.4(13) .
C41 C42 H42A 109.5 .
C41 C42 H42B 109.5 .
H42A C42 H42B 109.5 .
C41 C42 H42C 109.5 .
H42A C42 H42C 109.5 .
H42B C42 H42C 109.5 .
C41 C43 H43A 109.5 .
C41 C43 H43B 109.5 .
H43A C43 H43B 109.5 .
C41 C43 H43C 109.5 .
H43A C43 H43C 109.5 .
H43B C43 H43C 109.5 .
C41 C44 H44A 109.5 .
C41 C44 H44B 109.5 .
H44A C44 H44B 109.5 .
C41 C44 H44C 109.5 .
H44A C44 H44C 109.5 .
H44B C44 H44C 109.5 .
C41 C142 H14E 109.5 .
C41 C142 H14F 109.5 .
H14E C142 H14F 109.5 .
C41 C142 H14G 109.5 .
H14E C142 H14G 109.5 .
H14F C142 H14G 109.5 .
C41 C143 H14H 109.5 .
C41 C143 H14I 109.5 .
H14H C143 H14I 109.5 .
C41 C143 H14J 109.5 .
H14H C143 H14J 109.5 .
H14I C143 H14J 109.5 .
C41 C144 H14K 109.5 .
C41 C144 H14L 109.5 .
H14K C144 H14L 109.5 .
C41 C144 H14M 109.5 .
H14K C144 H14M 109.5 .
H14L C144 H14M 109.5 .
F1 B1 F2 109.15(19) .
F1 B1 N2 112.12(19) .
F2 B1 N2 109.8(2) .
F1 B1 N1 109.1(2) .
F2 B1 N1 108.95(19) .
N2 B1 N1 107.64(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 B1 1.389(3) .
F2 B1 1.394(3) .
N1 C1 1.341(3) .
N1 C4 1.414(2) .
N1 B1 1.557(3) .
N2 C9 1.374(3) .
N2 C6 1.418(3) .
N2 B1 1.529(3) .
C1 C2 1.440(3) .
C1 C21 1.489(3) .
C2 C10 1.387(3) 5_656
C2 C3 1.431(3) .
C3 C10 1.396(3) .
C3 C4 1.444(3) .
C4 C5 1.386(3) .
C5 C6 1.408(3) .
C5 C23 1.494(3) .
C6 C7 1.408(3) .
C7 C8 1.423(3) .
C7 C11 1.473(3) .
C8 C9 1.379(3) .
C8 C17 1.478(3) .
C9 C22 1.479(3) .
C10 H10 0.9500 .
C11 C12 1.386(3) .
C11 C16 1.420(3) .
C12 C13 1.425(3) .
C12 H12 0.9500 .
C13 C14 1.383(3) .
C13 C37 1.534(3) .
C14 C15 1.414(3) .
C14 H14 0.9500 .
C15 C16 1.406(3) .
C15 C20 1.424(3) .
C16 C17 1.412(3) .
C17 C18 1.364(3) .
C18 C19 1.434(3) .
C18 H18 0.9500 .
C19 C20 1.383(3) .
C19 C41 1.531(3) .
C20 H20 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C21 H21D 0.9800 .
C21 H21E 0.9800 .
C21 H21F 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C22 H22D 0.9800 .
C22 H22E 0.9800 .
C22 H22F 0.9800 .
C23 C28 1.390(3) .
C23 C24 1.395(3) .
C24 C25 1.392(3) .
C24 H24 0.9500 .
C25 C26 1.389(3) .
C25 C29 1.545(3) .
C26 C27 1.396(3) .
C26 H26 0.9500 .
C27 C28 1.397(3) .
C27 C33 1.550(3) .
C28 H28 0.9500 .
C29 C31 1.473(5) .
C29 C131 1.480(9) .
C29 C130 1.497(8) .
C29 C30 1.568(7) .
C29 C32 1.575(6) .
C29 C132 1.613(8) .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C130 H13A 0.9800 .
C130 H13B 0.9800 .
C130 H13C 0.9800 .
C131 H13D 0.9800 .
C131 H13E 0.9800 .
C131 H13F 0.9800 .
C132 H13G 0.9800 .
C132 H13H 0.9800 .
C132 H13I 0.9800 .
C33 C34 1.525(3) .
C33 C36 1.531(3) .
C33 C35 1.547(4) .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
C35 H35A 0.9800 .
C35 H35B 0.9800 .
C35 H35C 0.9800 .
C36 H36A 0.9800 .
C36 H36B 0.9800 .
C36 H36C 0.9800 .
C37 C40 1.500(4) .
C37 C38 1.506(4) .
C37 C39 1.563(4) .
C38 H38A 0.9800 .
C38 H38B 0.9800 .
C38 H38C 0.9800 .
C39 H39A 0.9800 .
C39 H39B 0.9800 .
C39 H39C 0.9800 .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C40 H40C 0.9800 .
C41 C143 1.488(13) .
C41 C43 1.515(4) .
C41 C42 1.530(4) .
C41 C44 1.536(4) .
C41 C144 1.565(14) .
C41 C142 1.617(14) .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
C43 H43A 0.9800 .
C43 H43B 0.9800 .
C43 H43C 0.9800 .
C44 H44A 0.9800 .
C44 H44B 0.9800 .
C44 H44C 0.9800 .
C142 H14E 0.9800 .
C142 H14F 0.9800 .
C142 H14G 0.9800 .
C143 H14H 0.9800 .
C143 H14I 0.9800 .
C143 H14J 0.9800 .
C144 H14K 0.9800 .
C144 H14L 0.9800 .
C144 H14M 0.9800 .
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_4
C4 N1 C1 C2 0.9(3) . .
B1 N1 C1 C2 178.8(2) . .
C4 N1 C1 C21 -177.8(2) . .
B1 N1 C1 C21 0.1(3) . .
N1 C1 C2 C10 -179.1(2) . 5_656
C21 C1 C2 C10 -0.4(4) . 5_656
N1 C1 C2 C3 -0.7(3) . .
C21 C1 C2 C3 178.0(2) . .
C10 C2 C3 C10 0.5(4) 5_656 .
C1 C2 C3 C10 -178.0(2) . .
C10 C2 C3 C4 178.7(2) 5_656 .
C1 C2 C3 C4 0.1(2) . .
C1 N1 C4 C5 178.9(2) . .
B1 N1 C4 C5 1.0(3) . .
C1 N1 C4 C3 -0.8(2) . .
B1 N1 C4 C3 -178.7(2) . .
C10 C3 C4 C5 -1.6(4) . .
C2 C3 C4 C5 -179.3(2) . .
C10 C3 C4 N1 178.1(2) . .
C2 C3 C4 N1 0.4(2) . .
N1 C4 C5 C6 0.4(3) . .
C3 C4 C5 C6 -179.9(2) . .
N1 C4 C5 C23 -179.13(19) . .
C3 C4 C5 C23 0.6(4) . .
C4 C5 C6 C7 177.4(2) . .
C23 C5 C6 C7 -3.0(4) . .
C4 C5 C6 N2 -2.1(3) . .
C23 C5 C6 N2 177.39(19) . .
C9 N2 C6 C7 1.1(2) . .
B1 N2 C6 C7 -177.1(2) . .
C9 N2 C6 C5 -179.2(2) . .
B1 N2 C6 C5 2.6(3) . .
C5 C6 C7 C8 -179.8(2) . .
N2 C6 C7 C8 -0.2(2) . .
C5 C6 C7 C11 0.7(5) . .
N2 C6 C7 C11 -179.7(3) . .
C6 C7 C8 C9 -0.8(3) . .
C11 C7 C8 C9 178.95(19) . .
C6 C7 C8 C17 178.98(18) . .
C11 C7 C8 C17 -1.3(3) . .
C6 N2 C9 C8 -1.6(3) . .
B1 N2 C9 C8 176.6(2) . .
C6 N2 C9 C22 176.8(2) . .
B1 N2 C9 C22 -5.0(4) . .
C7 C8 C9 N2 1.5(3) . .
C17 C8 C9 N2 -178.1(3) . .
C7 C8 C9 C22 -176.8(3) . .
C17 C8 C9 C22 3.6(5) . .
C2 C3 C10 C2 -0.5(3) . 5_656
C4 C3 C10 C2 -178.0(2) . 5_656
C6 C7 C11 C12 0.3(5) . .
C8 C7 C11 C12 -179.2(3) . .
C6 C7 C11 C16 179.6(3) . .
C8 C7 C11 C16 0.1(2) . .
C16 C11 C12 C13 1.1(3) . .
C7 C11 C12 C13 -179.6(2) . .
C11 C12 C13 C14 -0.2(3) . .
C11 C12 C13 C37 -179.6(2) . .
C12 C13 C14 C15 0.5(4) . .
C37 C13 C14 C15 179.9(2) . .
C13 C14 C15 C16 -1.6(3) . .
C13 C14 C15 C20 178.5(2) . .
C14 C15 C16 C17 179.3(2) . .
C20 C15 C16 C17 -0.8(3) . .
C14 C15 C16 C11 2.6(3) . .
C20 C15 C16 C11 -177.5(2) . .
C12 C11 C16 C15 -2.4(3) . .
C7 C11 C16 C15 178.1(2) . .
C12 C11 C16 C17 -179.3(2) . .
C7 C11 C16 C17 1.2(3) . .
C15 C16 C17 C18 0.5(4) . .
C11 C16 C17 C18 177.5(2) . .
C15 C16 C17 C8 -178.9(2) . .
C11 C16 C17 C8 -1.9(3) . .
C9 C8 C17 C18 2.3(5) . .
C7 C8 C17 C18 -177.3(3) . .
C9 C8 C17 C16 -178.5(3) . .
C7 C8 C17 C16 1.9(3) . .
C16 C17 C18 C19 -0.1(4) . .
C8 C17 C18 C19 179.1(2) . .
C17 C18 C19 C20 0.1(4) . .
C17 C18 C19 C41 -178.2(2) . .
C18 C19 C20 C15 -0.5(4) . .
C41 C19 C20 C15 177.8(2) . .
C16 C15 C20 C19 0.8(3) . .
C14 C15 C20 C19 -179.3(2) . .
C4 C5 C23 C28 -85.0(3) . .
C6 C5 C23 C28 95.4(3) . .
C4 C5 C23 C24 88.2(3) . .
C6 C5 C23 C24 -91.4(3) . .
C28 C23 C24 C25 1.3(3) . .
C5 C23 C24 C25 -172.0(2) . .
C23 C24 C25 C26 -1.8(3) . .
C23 C24 C25 C29 175.1(2) . .
C24 C25 C26 C27 0.8(3) . .
C29 C25 C26 C27 -176.1(2) . .
C25 C26 C27 C28 0.7(4) . .
C25 C26 C27 C33 174.2(2) . .
C24 C23 C28 C27 0.2(3) . .
C5 C23 C28 C27 173.3(2) . .
C26 C27 C28 C23 -1.2(3) . .
C33 C27 C28 C23 -174.8(2) . .
C26 C25 C29 C31 -18.3(5) . .
C24 C25 C29 C31 165.0(5) . .
C26 C25 C29 C131 143.0(6) . .
C24 C25 C29 C131 -33.8(6) . .
C26 C25 C29 C130 -89.3(5) . .
C24 C25 C29 C130 94.0(5) . .
C26 C25 C29 C30 106.7(4) . .
C24 C25 C29 C30 -70.0(4) . .
C26 C25 C29 C32 -138.3(3) . .
C24 C25 C29 C32 45.0(4) . .
C26 C25 C29 C132 24.8(6) . .
C24 C25 C29 C132 -152.0(6) . .
C26 C27 C33 C34 142.9(2) . .
C28 C27 C33 C34 -43.8(3) . .
C26 C27 C33 C36 21.4(3) . .
C28 C27 C33 C36 -165.3(2) . .
C26 C27 C33 C35 -97.1(3) . .
C28 C27 C33 C35 76.3(3) . .
C14 C13 C37 C40 -5.9(4) . .
C12 C13 C37 C40 173.5(2) . .
C14 C13 C37 C38 121.4(3) . .
C12 C13 C37 C38 -59.2(3) . .
C14 C13 C37 C39 -122.2(3) . .
C12 C13 C37 C39 57.2(3) . .
C20 C19 C41 C143 -177.6(12) . .
C18 C19 C41 C143 0.7(13) . .
C20 C19 C41 C43 2.7(4) . .
C18 C19 C41 C43 -179.0(3) . .
C20 C19 C41 C42 125.0(3) . .
C18 C19 C41 C42 -56.7(3) . .
C20 C19 C41 C44 -116.9(3) . .
C18 C19 C41 C44 61.4(3) . .
C20 C19 C41 C144 62.0(12) . .
C18 C19 C41 C144 -119.6(11) . .
C20 C19 C41 C142 -52.3(10) . .
C18 C19 C41 C142 126.0(10) . .
C9 N2 B1 F1 60.9(3) . .
C6 N2 B1 F1 -121.2(2) . .
C9 N2 B1 F2 -60.6(3) . .
C6 N2 B1 F2 117.3(2) . .
C9 N2 B1 N1 -179.1(2) . .
C6 N2 B1 N1 -1.2(3) . .
C1 N1 B1 F1 -56.3(3) . .
C4 N1 B1 F1 121.2(2) . .
C1 N1 B1 F2 62.7(3) . .
C4 N1 B1 F2 -119.7(2) . .
C1 N1 B1 N2 -178.24(19) . .
C4 N1 B1 N2 -0.7(3) . .
