#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:24:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178431 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025288.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_4025288
loop_
_publ_author_name
'Andrew C. Benniston'
'Graeme Copley'
'Anthony Harriman'
'David Howgego'
'Ross W. Harrington'
'William Clegg'
_publ_section_title
;
 Cofacial Boron Dipyrromethene (Bodipy) Dimers: Synthesis, Charge
 Delocalization, and Exciton Coupling
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2018
_journal_page_last               2027
_journal_paper_doi               10.1021/jo1000803
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C46 H50 B2 F4 N4 O, 2 C H2 Cl2'
_chemical_formula_sum            'C48 H54 B2 Cl4 F4 N4 O'
_chemical_formula_weight         942.37
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.082(4)
_cell_angle_beta                 93.827(5)
_cell_angle_gamma                118.721(6)
_cell_formula_units_Z            2
_cell_length_a                   11.2976(7)
_cell_length_b                   11.6097(6)
_cell_length_c                   20.8444(11)
_cell_measurement_reflns_used    4856
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.55
_cell_measurement_theta_min      3.07
_cell_volume                     2354.3(3)
_computing_cell_refinement       'Oxford Diffraction CrysAlisPro'
_computing_data_collection       'Oxford Diffraction CrysAlisPro'
_computing_data_reduction        'Oxford Diffraction CrysAlisPro'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Oxford Diffraction Gemini A Ultra diffractometer'
_diffrn_measurement_method       'thick-slice ω scans'
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.1476
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18841
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrysAlisPro
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.821
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         8220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.821
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0318P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                3945
_reflns_number_total             8220
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo1000803_si_002_2.cif
_cod_data_source_block           acb61_BD2
_cod_original_cell_volume        2354.3(2)
_cod_database_code               4025288
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.77433(8) 0.87155(9) 0.29835(5) 0.0521(3) Uani 1 1 d . . .
Cl2 Cl 0.20054(10) 0.63610(8) 0.25766(5) 0.0617(3) Uani 1 1 d . . .
Cl3 Cl 0.58432(9) 0.97256(9) 0.30466(6) 0.0749(4) Uani 1 1 d . . .
Cl4 Cl 0.04101(9) 0.76911(11) 0.28034(6) 0.0781(4) Uani 1 1 d . . .
O1 O 0.37502(15) 0.43673(15) 0.22675(9) 0.0186(4) Uani 1 1 d . . .
F1 F 0.35275(15) 0.81109(14) 0.42733(9) 0.0398(5) Uani 1 1 d . . .
F2 F 0.34790(15) 0.71722(16) 0.51718(8) 0.0422(5) Uani 1 1 d . . .
F3 F 0.35607(13) 0.90033(13) 0.15167(8) 0.0312(4) Uani 1 1 d . . .
F4 F 0.35848(14) 0.86297(14) 0.04283(8) 0.0315(4) Uani 1 1 d . . .
N1 N 0.2335(2) 0.5709(2) 0.41396(11) 0.0215(6) Uani 1 1 d . . .
N2 N 0.4856(2) 0.70062(19) 0.43788(11) 0.0209(6) Uani 1 1 d . . .
N3 N 0.49170(19) 0.80430(18) 0.11260(11) 0.0172(5) Uani 1 1 d . . .
N4 N 0.23937(19) 0.67258(19) 0.09541(11) 0.0182(5) Uani 1 1 d . . .
B1 B 0.3554(3) 0.7048(3) 0.45052(18) 0.0270(9) Uani 1 1 d . . .
B2 B 0.3605(3) 0.8130(3) 0.10027(18) 0.0227(8) Uani 1 1 d . . .
C1 C 0.1006(3) 0.5329(3) 0.41290(14) 0.0254(7) Uani 1 1 d . . .
C2 C 0.0199(3) 0.4043(3) 0.37545(14) 0.0255(7) Uani 1 1 d . . .
C3 C 0.1079(2) 0.3641(2) 0.35149(14) 0.0222(7) Uani 1 1 d . . .
C4 C 0.2429(2) 0.4676(2) 0.37624(14) 0.0191(7) Uani 1 1 d . . .
C5 C 0.3702(2) 0.4796(2) 0.37085(13) 0.0180(7) Uani 1 1 d . . .
C6 C 0.4911(2) 0.5939(2) 0.40190(13) 0.0193(7) Uani 1 1 d . . .
C7 C 0.6300(2) 0.6276(2) 0.40417(14) 0.0221(7) Uani 1 1 d . . .
C8 C 0.7067(2) 0.7544(2) 0.44170(14) 0.0220(7) Uani 1 1 d . . .
C9 C 0.6159(3) 0.7974(2) 0.46122(14) 0.0237(7) Uani 1 1 d . . .
C10 C 0.0534(3) 0.6216(3) 0.44619(15) 0.0353(8) Uani 1 1 d . . .
H10A H 0.1163 0.6751 0.4864 0.053 Uiso 1 1 calc R . .
H10B H -0.0382 0.5670 0.4570 0.053 Uiso 1 1 calc R . .
H10C H 0.0512 0.6809 0.4171 0.053 Uiso 1 1 calc R . .
C11 C -0.1336(2) 0.3268(3) 0.36453(15) 0.0342(8) Uani 1 1 d . . .
H11A H -0.1684 0.3639 0.3990 0.041 Uiso 1 1 calc R . .
H11B H -0.1644 0.2327 0.3683 0.041 Uiso 1 1 calc R . .
C12 C -0.1932(3) 0.3315(3) 0.29793(16) 0.0420(9) Uani 1 1 d . . .
H12A H -0.2930 0.2842 0.2939 0.063 Uiso 1 1 calc R . .
H12B H -0.1646 0.2887 0.2636 0.063 Uiso 1 1 calc R . .
H12C H -0.1603 0.4247 0.2934 0.063 Uiso 1 1 calc R . .
C13 C 0.0649(3) 0.2349(3) 0.30649(15) 0.0333(8) Uani 1 1 d . . .
H13A H -0.0340 0.1771 0.3032 0.050 Uiso 1 1 calc R . .
H13B H 0.1116 0.1904 0.3238 0.050 Uiso 1 1 calc R . .
H13C H 0.0889 0.2530 0.2631 0.050 Uiso 1 1 calc R . .
C14 C 0.6885(3) 0.5469(3) 0.37199(16) 0.0343(8) Uani 1 1 d . . .
H14A H 0.7872 0.6036 0.3741 0.051 Uiso 1 1 calc R . .
H14B H 0.6462 0.5123 0.3262 0.051 Uiso 1 1 calc R . .
H14C H 0.6701 0.4722 0.3947 0.051 Uiso 1 1 calc R . .
C15 C 0.8581(3) 0.8304(3) 0.46040(15) 0.0316(8) Uani 1 1 d . . .
H15A H 0.8898 0.9273 0.4670 0.038 Uiso 1 1 calc R . .
H15B H 0.9014 0.8094 0.4244 0.038 Uiso 1 1 calc R . .
C16 C 0.9024(3) 0.7964(3) 0.52273(16) 0.0387(8) Uani 1 1 d . . .
H16A H 1.0021 0.8380 0.5301 0.058 Uiso 1 1 calc R . .
H16B H 0.8618 0.6993 0.5183 0.058 Uiso 1 1 calc R . .
H16C H 0.8718 0.8300 0.5598 0.058 Uiso 1 1 calc R . .
C17 C 0.6495(3) 0.9295(3) 0.49946(15) 0.0342(8) Uani 1 1 d . . .
H17A H 0.5763 0.9182 0.5252 0.051 Uiso 1 1 calc R . .
H17B H 0.6587 0.9910 0.4694 0.051 Uiso 1 1 calc R . .
H17C H 0.7355 0.9659 0.5289 0.051 Uiso 1 1 calc R . .
C18 C 0.3805(2) 0.3511(2) 0.26664(14) 0.0171(7) Uani 1 1 d . . .
C19 C 0.3795(2) 0.3676(2) 0.33345(14) 0.0181(7) Uani 1 1 d . . .
C20 C 0.3907(2) 0.2731(2) 0.36446(15) 0.0240(7) Uani 1 1 d . . .
H20A H 0.3917 0.2805 0.4104 0.029 Uiso 1 1 calc R . .
C21 C 0.4004(3) 0.1679(2) 0.33016(15) 0.0261(7) Uani 1 1 d . . .
H21A H 0.4076 0.1053 0.3532 0.031 Uiso 1 1 calc R . .
C22 C 0.3998(2) 0.1527(3) 0.26354(15) 0.0244(7) Uani 1 1 d . . .
H22A H 0.4060 0.0804 0.2405 0.029 Uiso 1 1 calc R . .
C23 C 0.3898(2) 0.2463(2) 0.23077(14) 0.0164(6) Uani 1 1 d . . .
C24 C 0.3897(2) 0.2675(2) 0.16423(14) 0.0182(7) Uani 1 1 d . . .
C25 C 0.3962(2) 0.2013(2) 0.10509(15) 0.0224(7) Uani 1 1 d . . .
H25A H 0.4002 0.1211 0.1033 0.027 Uiso 1 1 calc R . .
C26 C 0.3968(3) 0.2539(3) 0.04938(15) 0.0264(7) Uani 1 1 d . . .
H26A H 0.4025 0.2102 0.0090 0.032 Uiso 1 1 calc R . .
C27 C 0.3891(2) 0.3706(2) 0.05135(15) 0.0227(7) Uani 1 1 d . . .
H27A H 0.3891 0.4043 0.0121 0.027 Uiso 1 1 calc R . .
C28 C 0.3813(2) 0.4393(2) 0.10931(14) 0.0185(7) Uani 1 1 d . . .
C29 C 0.3816(2) 0.3845(2) 0.16443(14) 0.0159(6) Uani 1 1 d . . .
C30 C 0.6215(2) 0.9067(2) 0.12101(14) 0.0205(7) Uani 1 1 d . . .
C31 C 0.7128(2) 0.8580(2) 0.13096(14) 0.0222(7) Uani 1 1 d . . .
C32 C 0.6352(2) 0.7208(2) 0.12885(13) 0.0195(7) Uani 1 1 d . . .
C33 C 0.4960(2) 0.6870(2) 0.11712(13) 0.0172(6) Uani 1 1 d . . .
C34 C 0.3743(2) 0.5648(2) 0.10953(13) 0.0163(6) Uani 1 1 d . . .
C35 C 0.2483(2) 0.5571(2) 0.09926(13) 0.0177(7) Uani 1 1 d . . .
C36 C 0.1115(2) 0.4469(2) 0.09110(13) 0.0198(7) Uani 1 1 d . . .
C37 C 0.0248(2) 0.4982(2) 0.08279(14) 0.0219(7) Uani 1 1 d . . .
C38 C 0.1064(3) 0.6374(2) 0.08606(14) 0.0207(7) Uani 1 1 d . . .
C39 C 0.6545(3) 1.0471(2) 0.11867(16) 0.0306(8) Uani 1 1 d . . .
H39A H 0.6099 1.0748 0.1510 0.046 Uiso 1 1 calc R . .
H39B H 0.6219 1.0523 0.0749 0.046 Uiso 1 1 calc R . .
H39C H 0.7535 1.1063 0.1285 0.046 Uiso 1 1 calc R . .
C40 C 0.8653(2) 0.9419(3) 0.14020(15) 0.0296(8) Uani 1 1 d . . .
H40A H 0.9057 0.9013 0.1669 0.036 Uiso 1 1 calc R . .
H40B H 0.8924 1.0318 0.1644 0.036 Uiso 1 1 calc R . .
C41 C 0.9223(3) 0.9556(3) 0.07531(15) 0.0345(8) Uani 1 1 d . . .
H41A H 1.0217 1.0123 0.0838 0.052 Uiso 1 1 calc R . .
H41B H 0.8828 0.9962 0.0487 0.052 Uiso 1 1 calc R . .
H41C H 0.8988 0.8672 0.0519 0.052 Uiso 1 1 calc R . .
C42 C 0.6921(3) 0.6305(3) 0.14046(15) 0.0287(8) Uani 1 1 d . . .
H42A H 0.7919 0.6827 0.1487 0.043 Uiso 1 1 calc R . .
H42B H 0.6634 0.5608 0.1018 0.043 Uiso 1 1 calc R . .
H42C H 0.6580 0.5891 0.1784 0.043 Uiso 1 1 calc R . .
C43 C 0.0686(2) 0.3048(2) 0.09515(15) 0.0282(8) Uani 1 1 d . . .
H43A H -0.0304 0.2499 0.0825 0.042 Uiso 1 1 calc R . .
H43B H 0.0933 0.2985 0.1400 0.042 Uiso 1 1 calc R . .
H43C H 0.1146 0.2729 0.0655 0.042 Uiso 1 1 calc R . .
C44 C -0.1285(2) 0.4241(3) 0.07503(15) 0.0260(7) Uani 1 1 d . . .
H44A H -0.1633 0.3341 0.0488 0.031 Uiso 1 1 calc R . .
H44B H -0.1641 0.4720 0.0509 0.031 Uiso 1 1 calc R . .
C45 C -0.1807(3) 0.4105(3) 0.14038(15) 0.0329(8) Uani 1 1 d . . .
H45A H -0.2806 0.3651 0.1333 0.049 Uiso 1 1 calc R . .
H45B H -0.1448 0.4993 0.1668 0.049 Uiso 1 1 calc R . .
H45C H -0.1505 0.3583 0.1632 0.049 Uiso 1 1 calc R . .
C46 C 0.0595(3) 0.7370(3) 0.08111(15) 0.0304(8) Uani 1 1 d . . .
H46A H 0.1244 0.8090 0.0606 0.046 Uiso 1 1 calc R . .
H46B H 0.0542 0.7743 0.1249 0.046 Uiso 1 1 calc R . .
H46C H -0.0307 0.6931 0.0546 0.046 Uiso 1 1 calc R . .
C47 C 0.6012(3) 0.8297(3) 0.29119(16) 0.0397(8) Uani 1 1 d . . .
H47A H 0.5547 0.7784 0.2469 0.048 Uiso 1 1 calc R . .
H47B H 0.5564 0.7723 0.3233 0.048 Uiso 1 1 calc R . .
C48 C 0.2057(3) 0.7886(3) 0.28302(17) 0.0427(9) Uani 1 1 d . . .
H48A H 0.2571 0.8521 0.2544 0.051 Uiso 1 1 calc R . .
H48B H 0.2545 0.8267 0.3282 0.051 Uiso 1 1 calc R . .
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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables 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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C29 105.47(19) . . ?
B1 N1 C1 126.3(2) . . ?
B1 N1 C4 125.8(2) . . ?
C1 N1 C4 107.9(2) . . ?
B1 N2 C6 125.9(2) . . ?
B1 N2 C9 126.5(2) . . ?
C6 N2 C9 107.5(2) . . ?
B2 N3 C30 126.6(2) . . ?
B2 N3 C33 125.1(2) . . ?
C30 N3 C33 108.2(2) . . ?
B2 N4 C35 125.5(2) . . ?
B2 N4 C38 126.5(2) . . ?
C35 N4 C38 108.08(19) . . ?
F1 B1 F2 109.3(2) . . ?
F1 B1 N1 109.9(2) . . ?
F1 B1 N2 111.0(2) . . ?
F2 B1 N1 109.8(2) . . ?
F2 B1 N2 109.9(2) . . ?
N1 B1 N2 106.8(2) . . ?
F3 B2 F4 107.8(2) . . ?
F3 B2 N3 110.3(2) . . ?
F3 B2 N4 110.2(2) . . ?
F4 B2 N3 109.8(2) . . ?
F4 B2 N4 111.2(2) . . ?
N3 B2 N4 107.6(2) . . ?
N1 C1 C2 110.0(2) . . ?
N1 C1 C10 122.2(2) . . ?
C2 C1 C10 127.7(2) . . ?
C1 C2 C3 107.2(2) . . ?
C1 C2 C11 125.5(2) . . ?
C3 C2 C11 127.3(3) . . ?
C2 C3 C4 107.3(2) . . ?
C2 C3 C13 125.0(2) . . ?
C4 C3 C13 127.6(2) . . ?
N1 C4 C3 107.5(2) . . ?
N1 C4 C5 119.8(2) . . ?
C3 C4 C5 132.7(2) . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 C19 119.7(2) . . ?
C6 C5 C19 118.7(2) . . ?
N2 C6 C5 120.0(2) . . ?
N2 C6 C7 108.2(2) . . ?
C5 C6 C7 131.7(2) . . ?
C6 C7 C8 106.8(2) . . ?
C6 C7 C14 128.4(2) . . ?
C8 C7 C14 124.8(2) . . ?
C7 C8 C9 107.6(2) . . ?
C7 C8 C15 126.7(2) . . ?
C9 C8 C15 125.6(2) . . ?
N2 C9 C8 109.8(2) . . ?
N2 C9 C17 122.4(2) . . ?
C8 C9 C17 127.8(2) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 109.2 . . ?
C2 C11 H11B 109.2 . . ?
C2 C11 C12 112.2(2) . . ?
H11A C11 H11B 107.9 . . ?
H11A C11 C12 109.2 . . ?
H11B C11 C12 109.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.3 . . ?
C8 C15 H15B 109.3 . . ?
C8 C15 C16 111.7(2) . . ?
H15A C15 H15B 107.9 . . ?
H15A C15 C16 109.3 . . ?
H15B C15 C16 109.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 C19 124.9(2) . . ?
O1 C18 C23 111.4(2) . . ?
C19 C18 C23 123.7(2) . . ?
C5 C19 C18 123.1(2) . . ?
C5 C19 C20 121.2(3) . . ?
C18 C19 C20 115.6(2) . . ?
C19 C20 H20A 119.0 . . ?
C19 C20 C21 122.0(3) . . ?
H20A C20 C21 119.0 . . ?
C20 C21 H21A 119.3 . . ?
C20 C21 C22 121.4(3) . . ?
H21A C21 C22 119.3 . . ?
C21 C22 C23 118.3(3) . . ?
C21 C22 H22A 120.8 . . ?
C23 C22 H22A 120.8 . . ?
C18 C23 C22 119.0(3) . . ?
C18 C23 C24 105.8(2) . . ?
C22 C23 C24 135.2(2) . . ?
C23 C24 C25 135.2(2) . . ?
C23 C24 C29 106.2(2) . . ?
C25 C24 C29 118.6(3) . . ?
C24 C25 H25A 120.5 . . ?
C24 C25 C26 119.0(2) . . ?
H25A C25 C26 120.5 . . ?
C25 C26 H26A 119.6 . . ?
C25 C26 C27 120.9(3) . . ?
H26A C26 C27 119.6 . . ?
C26 C27 H27A 119.0 . . ?
C26 C27 C28 122.0(3) . . ?
H27A C27 C28 119.0 . . ?
C27 C28 C29 115.8(2) . . ?
C27 C28 C34 120.4(3) . . ?
C29 C28 C34 123.8(2) . . ?
O1 C29 C24 111.1(2) . . ?
O1 C29 C28 125.2(2) . . ?
C24 C29 C28 123.7(3) . . ?
N3 C30 C31 109.4(2) . . ?
N3 C30 C39 122.5(2) . . ?
C31 C30 C39 128.1(2) . . ?
C30 C31 C32 107.5(2) . . ?
C30 C31 C40 124.7(2) . . ?
C32 C31 C40 127.8(2) . . ?
C31 C32 C33 107.0(2) . . ?
C31 C32 C42 125.1(2) . . ?
C33 C32 C42 127.9(2) . . ?
N3 C33 C32 107.9(2) . . ?
N3 C33 C34 120.0(2) . . ?
C32 C33 C34 132.1(2) . . ?
C28 C34 C33 119.1(2) . . ?
C28 C34 C35 119.3(2) . . ?
C33 C34 C35 121.5(2) . . ?
N4 C35 C34 120.3(2) . . ?
N4 C35 C36 107.5(2) . . ?
C34 C35 C36 132.2(2) . . ?
C35 C36 C37 106.9(2) . . ?
C35 C36 C43 127.4(2) . . ?
C37 C36 C43 125.6(2) . . ?
C36 C37 C38 107.5(2) . . ?
C36 C37 C44 127.5(2) . . ?
C38 C37 C44 124.9(2) . . ?
N4 C38 C37 110.0(2) . . ?
N4 C38 C46 122.4(2) . . ?
C37 C38 C46 127.6(2) . . ?
C30 C39 H39A 109.5 . . ?
C30 C39 H39B 109.5 . . ?
C30 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C31 C40 H40A 109.1 . . ?
C31 C40 H40B 109.1 . . ?
C31 C40 C41 112.4(2) . . ?
H40A C40 H40B 107.8 . . ?
H40A C40 C41 109.1 . . ?
H40B C40 C41 109.1 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C32 C42 H42A 109.5 . . ?
C32 C42 H42B 109.5 . . ?
C32 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C36 C43 H43A 109.5 . . ?
C36 C43 H43B 109.5 . . ?
C36 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C37 C44 H44A 109.2 . . ?
C37 C44 H44B 109.2 . . ?
C37 C44 C45 112.0(2) . . ?
H44A C44 H44B 107.9 . . ?
H44A C44 C45 109.2 . . ?
H44B C44 C45 109.2 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C38 C46 H46A 109.5 . . ?
C38 C46 H46B 109.5 . . ?
C38 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
Cl1 C47 Cl3 111.28(16) . . ?
Cl1 C47 H47A 109.4 . . ?
Cl1 C47 H47B 109.4 . . ?
Cl3 C47 H47A 109.4 . . ?
Cl3 C47 H47B 109.4 . . ?
H47A C47 H47B 108.0 . . ?
Cl2 C48 Cl4 111.72(16) . . ?
Cl2 C48 H48A 109.3 . . ?
Cl2 C48 H48B 109.3 . . ?
Cl4 C48 H48A 109.3 . . ?
Cl4 C48 H48B 109.3 . . ?
H48A C48 H48B 107.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C47 1.765(3) . ?
Cl2 C48 1.756(3) . ?
Cl3 C47 1.750(3) . ?
Cl4 C48 1.759(3) . ?
O1 C18 1.393(3) . ?
O1 C29 1.386(3) . ?
F1 B1 1.392(4) . ?
F2 B1 1.392(4) . ?
F3 B2 1.402(4) . ?
F4 B2 1.397(4) . ?
N1 B1 1.550(4) . ?
N1 C1 1.344(3) . ?
N1 C4 1.403(3) . ?
N2 B1 1.534(4) . ?
N2 C6 1.398(3) . ?
N2 C9 1.359(3) . ?
N3 B2 1.541(4) . ?
N3 C30 1.354(3) . ?
N3 C33 1.401(3) . ?
N4 B2 1.529(4) . ?
N4 C35 1.403(3) . ?
N4 C38 1.346(3) . ?
C1 C2 1.407(4) . ?
C1 C10 1.492(4) . ?
C2 C3 1.382(3) . ?
C2 C11 1.505(3) . ?
C3 C4 1.420(3) . ?
C3 C13 1.502(4) . ?
C4 C5 1.390(3) . ?
C5 C6 1.405(3) . ?
C5 C19 1.484(3) . ?
C6 C7 1.418(3) . ?
C7 C8 1.389(3) . ?
C7 C14 1.505(4) . ?
C8 C9 1.401(4) . ?
C8 C15 1.494(3) . ?
C9 C17 1.494(4) . ?
C10 H10A 0.980 . ?
C10 H10B 0.980 . ?
C10 H10C 0.980 . ?
C11 H11A 0.990 . ?
C11 H11B 0.990 . ?
C11 C12 1.521(4) . ?
C12 H12A 0.980 . ?
C12 H12B 0.980 . ?
C12 H12C 0.980 . ?
C13 H13A 0.980 . ?
C13 H13B 0.980 . ?
C13 H13C 0.980 . ?
C14 H14A 0.980 . ?
C14 H14B 0.980 . ?
C14 H14C 0.980 . ?
C15 H15A 0.990 . ?
C15 H15B 0.990 . ?
C15 C16 1.524(4) . ?
C16 H16A 0.980 . ?
C16 H16B 0.980 . ?
C16 H16C 0.980 . ?
C17 H17A 0.980 . ?
C17 H17B 0.980 . ?
C17 H17C 0.980 . ?
C18 C19 1.384(4) . ?
C18 C23 1.400(3) . ?
C19 C20 1.391(4) . ?
C20 H20A 0.950 . ?
C20 C21 1.392(4) . ?
C21 H21A 0.950 . ?
C21 C22 1.377(4) . ?
C22 H22A 0.950 . ?
C22 C23 1.397(4) . ?
C23 C24 1.438(4) . ?
C24 C25 1.396(4) . ?
C24 C29 1.404(3) . ?
C25 H25A 0.950 . ?
C25 C26 1.376(4) . ?
C26 H26A 0.950 . ?
C26 C27 1.395(3) . ?
C27 H27A 0.950 . ?
C27 C28 1.396(4) . ?
C28 C29 1.381(4) . ?
C28 C34 1.495(3) . ?
C30 C31 1.410(3) . ?
C30 C39 1.495(3) . ?
C31 C32 1.394(3) . ?
C31 C40 1.500(3) . ?
C32 C33 1.420(3) . ?
C32 C42 1.504(3) . ?
C33 C34 1.403(3) . ?
C34 C35 1.383(3) . ?
C35 C36 1.437(3) . ?
C36 C37 1.382(3) . ?
C36 C43 1.494(3) . ?
C37 C38 1.414(3) . ?
C37 C44 1.504(3) . ?
C38 C46 1.497(3) . ?
C39 H39A 0.980 . ?
C39 H39B 0.980 . ?
C39 H39C 0.980 . ?
C40 H40A 0.990 . ?
C40 H40B 0.990 . ?
C40 C41 1.530(4) . ?
C41 H41A 0.980 . ?
C41 H41B 0.980 . ?
C41 H41C 0.980 . ?
C42 H42A 0.980 . ?
C42 H42B 0.980 . ?
C42 H42C 0.980 . ?
C43 H43A 0.980 . ?
C43 H43B 0.980 . ?
C43 H43C 0.980 . ?
C44 H44A 0.990 . ?
C44 H44B 0.990 . ?
C44 C45 1.516(4) . ?
C45 H45A 0.980 . ?
C45 H45B 0.980 . ?
C45 H45C 0.980 . ?
C46 H46A 0.980 . ?
C46 H46B 0.980 . ?
C46 H46C 0.980 . ?
C47 H47A 0.990 . ?
C47 H47B 0.990 . ?
C48 H48A 0.990 . ?
C48 H48B 0.990 . ?
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
C6 N2 B1 F1 -121.7(3) . . . . ?
C6 N2 B1 F2 117.2(3) . . . . ?
C6 N2 B1 N1 -1.9(4) . . . . ?
C9 N2 B1 F1 60.7(4) . . . . ?
C9 N2 B1 F2 -60.4(4) . . . . ?
C9 N2 B1 N1 -179.5(2) . . . . ?
C1 N1 B1 F1 -60.4(4) . . . . ?
C1 N1 B1 F2 60.0(4) . . . . ?
C1 N1 B1 N2 179.1(2) . . . . ?
C4 N1 B1 F1 120.0(3) . . . . ?
C4 N1 B1 F2 -119.7(3) . . . . ?
C4 N1 B1 N2 -0.6(4) . . . . ?
C35 N4 B2 F3 -122.4(3) . . . . ?
C35 N4 B2 F4 118.2(3) . . . . ?
C35 N4 B2 N3 -2.1(4) . . . . ?
C38 N4 B2 F3 58.4(4) . . . . ?
C38 N4 B2 F4 -61.0(4) . . . . ?
C38 N4 B2 N3 178.7(2) . . . . ?
C30 N3 B2 F3 -58.6(4) . . . . ?
C30 N3 B2 F4 60.0(4) . . . . ?
C30 N3 B2 N4 -178.8(2) . . . . ?
C33 N3 B2 F3 121.3(3) . . . . ?
C33 N3 B2 F4 -120.1(3) . . . . ?
C33 N3 B2 N4 1.1(4) . . . . ?
B1 N1 C1 C2 -179.1(3) . . . . ?
B1 N1 C1 C10 2.6(4) . . . . ?
C4 N1 C1 C2 0.7(3) . . . . ?
C4 N1 C1 C10 -177.7(3) . . . . ?
N1 C1 C2 C3 -1.5(3) . . . . ?
N1 C1 C2 C11 178.3(3) . . . . ?
C10 C1 C2 C3 176.7(3) . . . . ?
C10 C1 C2 C11 -3.5(5) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C1 C2 C3 C13 -177.2(3) . . . . ?
C11 C2 C3 C4 -178.0(3) . . . . ?
C11 C2 C3 C13 3.1(5) . . . . ?
B1 N1 C4 C3 -179.9(3) . . . . ?
B1 N1 C4 C5 1.8(4) . . . . ?
C1 N1 C4 C3 0.4(3) . . . . ?
C1 N1 C4 C5 -178.0(3) . . . . ?
C2 C3 C4 N1 -1.3(3) . . . . ?
C2 C3 C4 C5 176.8(3) . . . . ?
C13 C3 C4 N1 177.5(3) . . . . ?
C13 C3 C4 C5 -4.4(5) . . . . ?
N1 C4 C5 C6 -0.6(4) . . . . ?
N1 C4 C5 C19 177.2(2) . . . . ?
C3 C4 C5 C6 -178.5(3) . . . . ?
C3 C4 C5 C19 -0.7(5) . . . . ?
B1 N2 C6 C5 3.1(4) . . . . ?
B1 N2 C6 C7 -177.6(3) . . . . ?
C9 N2 C6 C5 -178.9(2) . . . . ?
C9 N2 C6 C7 0.4(3) . . . . ?
C4 C5 C6 N2 -1.7(4) . . . . ?
C4 C5 C6 C7 179.1(3) . . . . ?
C19 C5 C6 N2 -179.6(2) . . . . ?
C19 C5 C6 C7 1.3(4) . . . . ?
N2 C6 C7 C8 0.2(3) . . . . ?
N2 C6 C7 C14 -178.7(3) . . . . ?
C5 C6 C7 C8 179.4(3) . . . . ?
C5 C6 C7 C14 0.6(5) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C6 C7 C8 C15 177.3(3) . . . . ?
C14 C7 C8 C9 178.2(3) . . . . ?
C14 C7 C8 C15 -3.9(5) . . . . ?
B1 N2 C9 C8 177.1(3) . . . . ?
B1 N2 C9 C17 -5.0(4) . . . . ?
C6 N2 C9 C8 -0.8(3) . . . . ?
C6 N2 C9 C17 177.0(3) . . . . ?
C7 C8 C9 N2 1.0(3) . . . . ?
C7 C8 C9 C17 -176.7(3) . . . . ?
C15 C8 C9 N2 -177.0(2) . . . . ?
C15 C8 C9 C17 5.3(5) . . . . ?
C1 C2 C11 C12 101.3(3) . . . . ?
C3 C2 C11 C12 -79.0(4) . . . . ?
C7 C8 C15 C16 -86.8(4) . . . . ?
C9 C8 C15 C16 90.7(3) . . . . ?
C29 O1 C18 C23 -0.2(2) . . . . ?
C29 O1 C18 C19 178.6(2) . . . . ?
C22 C23 C18 O1 178.4(2) . . . . ?
C22 C23 C18 C19 -0.5(3) . . . . ?
C24 C23 C18 O1 -0.2(3) . . . . ?
C24 C23 C18 C19 -179.1(2) . . . . ?
O1 C18 C19 C5 1.0(4) . . . . ?
O1 C18 C19 C20 -177.8(2) . . . . ?
C23 C18 C19 C5 179.7(2) . . . . ?
C23 C18 C19 C20 1.0(3) . . . . ?
C4 C5 C19 C18 86.4(3) . . . . ?
C4 C5 C19 C20 -94.9(3) . . . . ?
C6 C5 C19 C18 -95.7(3) . . . . ?
C6 C5 C19 C20 83.0(3) . . . . ?
C5 C19 C20 C21 -179.6(2) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
C18 C23 C22 C21 -0.2(3) . . . . ?
C24 C23 C22 C21 177.9(3) . . . . ?
C18 C23 C24 C25 -179.8(3) . . . . ?
C18 C23 C24 C29 0.5(3) . . . . ?
C22 C23 C24 C25 1.9(5) . . . . ?
C22 C23 C24 C29 -177.7(3) . . . . ?
C23 C24 C25 C26 -178.5(3) . . . . ?
C29 C24 C25 C26 1.1(3) . . . . ?
C24 C25 C26 C27 -0.9(4) . . . . ?
C25 C26 C27 C28 0.4(4) . . . . ?
C26 C27 C28 C29 0.0(3) . . . . ?
C26 C27 C28 C34 179.5(2) . . . . ?
C27 C28 C29 O1 179.8(2) . . . . ?
C27 C28 C29 C24 0.3(3) . . . . ?
C34 C28 C29 O1 0.3(4) . . . . ?
C34 C28 C29 C24 -179.2(2) . . . . ?
C18 O1 C29 C24 0.5(2) . . . . ?
C18 O1 C29 C28 -179.0(2) . . . . ?
C23 C24 C29 O1 -0.7(3) . . . . ?
C23 C24 C29 C28 178.9(2) . . . . ?
C25 C24 C29 O1 179.60(19) . . . . ?
C25 C24 C29 C28 -0.8(4) . . . . ?
B2 N3 C30 C31 -179.9(3) . . . . ?
B2 N3 C30 C39 -0.5(4) . . . . ?
C33 N3 C30 C31 0.2(3) . . . . ?
C33 N3 C30 C39 179.6(3) . . . . ?
N3 C30 C31 C32 -0.3(3) . . . . ?
N3 C30 C31 C40 178.2(3) . . . . ?
C39 C30 C31 C32 -179.7(3) . . . . ?
C39 C30 C31 C40 -1.1(5) . . . . ?
C30 C31 C32 C33 0.4(3) . . . . ?
C30 C31 C32 C42 -176.9(3) . . . . ?
C40 C31 C32 C33 -178.2(3) . . . . ?
C40 C31 C32 C42 4.6(5) . . . . ?
B2 N3 C33 C32 -179.9(3) . . . . ?
B2 N3 C33 C34 0.7(4) . . . . ?
C30 N3 C33 C32 0.0(3) . . . . ?
C30 N3 C33 C34 -179.4(2) . . . . ?
C31 C32 C33 N3 -0.2(3) . . . . ?
C31 C32 C33 C34 179.1(3) . . . . ?
C42 C32 C33 N3 176.9(3) . . . . ?
C42 C32 C33 C34 -3.8(5) . . . . ?
N3 C33 C34 C28 175.2(2) . . . . ?
N3 C33 C34 C35 -1.7(4) . . . . ?
C32 C33 C34 C28 -4.0(5) . . . . ?
C32 C33 C34 C35 179.0(3) . . . . ?
C27 C28 C34 C33 -86.7(3) . . . . ?
C27 C28 C34 C35 90.3(3) . . . . ?
C29 C28 C34 C33 92.7(3) . . . . ?
C29 C28 C34 C35 -90.2(3) . . . . ?
C28 C34 C35 N4 -176.2(2) . . . . ?
C28 C34 C35 C36 4.0(5) . . . . ?
C33 C34 C35 N4 0.7(4) . . . . ?
C33 C34 C35 C36 -179.0(3) . . . . ?
B2 N4 C35 C34 1.4(4) . . . . ?
B2 N4 C35 C36 -178.8(3) . . . . ?
C38 N4 C35 C34 -179.3(3) . . . . ?
C38 N4 C35 C36 0.5(3) . . . . ?
N4 C35 C36 C37 -0.1(3) . . . . ?
N4 C35 C36 C43 -176.3(3) . . . . ?
C34 C35 C36 C37 179.6(3) . . . . ?
C34 C35 C36 C43 3.4(5) . . . . ?
C35 C36 C37 C38 -0.2(3) . . . . ?
C35 C36 C37 C44 -177.4(3) . . . . ?
C43 C36 C37 C38 176.0(3) . . . . ?
C43 C36 C37 C44 -1.1(5) . . . . ?
B2 N4 C38 C37 178.7(3) . . . . ?
B2 N4 C38 C46 -2.0(4) . . . . ?
C35 N4 C38 C37 -0.6(3) . . . . ?
C35 N4 C38 C46 178.7(3) . . . . ?
C36 C37 C38 N4 0.6(3) . . . . ?
C36 C37 C38 C46 -178.7(3) . . . . ?
C44 C37 C38 N4 177.8(3) . . . . ?
C44 C37 C38 C46 -1.5(5) . . . . ?
C30 C31 C40 C41 -86.7(3) . . . . ?
C32 C31 C40 C41 91.5(4) . . . . ?
C36 C37 C44 C45 84.2(4) . . . . ?
C38 C37 C44 C45 -92.5(3) . . . . ?
