#------------------------------------------------------------------------------
#$Date: 2025-07-30 08:51:54 +0300 (Wed, 30 Jul 2025) $
#$Revision: 301408 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038513.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_4038513
loop_
_publ_author_name
'Wang, Dandan'
'Guo, Xing'
'Wu, Hao'
'Wu, Qinghua'
'Wang, Hua'
'Zhang, Xiankang'
'Hao, Erhong'
'Jiao, Lijuan'
_publ_section_title
;
 Visible Light Excitation of BODIPYs Enables Dehydrogenative Enamination
 at Their α-Positions with Aliphatic Amines.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8360
_journal_page_last               8370
_journal_paper_doi               10.1021/acs.joc.0c00620
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C22 H23 B F2 N3'
_chemical_formula_weight         377.91
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                114.162(2)
_cell_angle_beta                 102.168(2)
_cell_angle_gamma                93.667(2)
_cell_formula_units_Z            6
_cell_length_a                   10.9684(18)
_cell_length_b                   17.472(3)
_cell_length_c                   18.559(3)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.26
_cell_volume                     3126.8(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1725
_diffrn_reflns_av_unetI/netI     0.1436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31885
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.426
_diffrn_reflns_theta_min         1.245
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.298
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     767
_refine_ls_number_reflns         11492
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.299
_refine_ls_R_factor_all          0.2102
_refine_ls_R_factor_gt           0.0795
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0711P)²+4.3094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2757
_refine_ls_wR_factor_ref         0.3127
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6900
_reflns_number_total             11492
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00620_si_002.cif
_cod_data_source_block           test_0m
_cod_depositor_comments
;
Adding full bibliography for 4038510--4038515.cif.

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C66 H68 B3 F6 N9'
_cod_original_formula_weight         1133.72
_cod_original_formula_units_Z            2
_cod_original_cell_volume        3126.9(9)
_cod_database_code               4038513
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_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_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
F6 F 0.4322(3) 0.38758(18) 0.13915(19) 0.0682(9) Uani 1 1 d . . . . .
F4 F 0.2498(3) 0.5926(2) 0.11658(17) 0.0666(8) Uani 1 1 d . . . . .
F5 F 0.3999(3) 0.3463(2) 0.0049(2) 0.0716(9) Uani 1 1 d . . . . .
F3 F 0.1152(3) 0.52584(17) 0.15684(18) 0.0661(8) Uani 1 1 d . . . . .
N5 N 0.0565(3) 0.6445(2) 0.1313(2) 0.0438(9) Uani 1 1 d . . . . .
N7 N 0.6144(4) 0.3946(2) 0.0887(2) 0.0461(9) Uani 1 1 d . . . . .
N8 N 0.4961(4) 0.2560(2) 0.0592(2) 0.0488(10) Uani 1 1 d . . . . .
N4 N 0.2239(3) 0.6657(2) 0.2530(2) 0.0453(9) Uani 1 1 d . . . . .
N1 N 0.3512(4) 0.2588(3) 0.3428(2) 0.0532(10) Uani 1 1 d . . . . .
C49 C 0.7257(4) 0.2784(3) 0.0847(3) 0.0472(11) Uani 1 1 d . . . . .
N2 N 0.3617(4) 0.1804(3) 0.4277(2) 0.0552(11) Uani 1 1 d . . . . .
F1 F 0.3241(6) 0.3224(3) 0.4781(2) 0.1298(19) Uani 1 1 d . . . . .
C28 C 0.0099(4) 0.7145(3) 0.1792(3) 0.0452(11) Uani 1 1 d . . . . .
C50 C 0.6082(5) 0.2253(3) 0.0669(3) 0.0488(12) Uani 1 1 d . . . . .
C58 C 0.8419(5) 0.2402(3) 0.0916(3) 0.0494(12) Uani 1 1 d . . . . .
C36 C 0.0171(4) 0.8357(3) 0.3131(3) 0.0493(12) Uani 1 1 d . . . . .
C14 C 0.5907(5) 0.1117(3) 0.2946(3) 0.0501(12) Uani 1 1 d . . . . .
C23 C 0.3256(4) 0.6577(3) 0.3029(3) 0.0486(12) Uani 1 1 d . . . . .
C45 C 0.6443(5) 0.4775(3) 0.1042(3) 0.0488(12) Uani 1 1 d . . . . .
C27 C 0.0701(4) 0.7609(3) 0.2639(3) 0.0465(11) Uani 1 1 d . . . . .
C5 C 0.4931(5) 0.1561(3) 0.3332(3) 0.0496(12) Uani 1 1 d . . . . .
C26 C 0.1742(5) 0.7370(3) 0.2983(3) 0.0480(12) Uani 1 1 d . . . . .
C19 C 0.7178(5) 0.1494(3) 0.3268(3) 0.0555(13) Uani 1 1 d . . . . .
C29 C -0.0903(5) 0.7275(3) 0.1291(3) 0.0553(13) Uani 1 1 d . . . . .
H24 H -0.139133 0.769972 0.145451 0.066 Uiso 1 1 calc R U . . .
C6 C 0.4530(5) 0.1385(3) 0.3935(3) 0.0499(12) Uani 1 1 d . . . . .
C48 C 0.7253(4) 0.3596(3) 0.0938(3) 0.0473(11) Uani 1 1 d . . . . .
C4 C 0.4412(5) 0.2126(3) 0.3086(3) 0.0526(12) Uani 1 1 d . . . . .
B2 B 0.1614(5) 0.6049(4) 0.1623(3) 0.0468(13) Uani 1 1 d . . . . .
N9 N 0.5087(5) 0.6712(3) 0.1426(3) 0.0696(13) Uani 1 1 d . . . . .
H8 H 0.430231 0.651457 0.133285 0.084 Uiso 1 1 calc R U . . .
C31 C -0.0143(5) 0.6168(3) 0.0539(3) 0.0533(13) Uani 1 1 d . . . . .
H30 H -0.002750 0.570604 0.009156 0.064 Uiso 1 1 calc R U . . .
C59 C 0.8867(5) 0.1983(3) 0.0224(3) 0.0608(14) Uani 1 1 d . . . . .
C54 C 0.5558(5) 0.5315(3) 0.1080(3) 0.0537(13) Uani 1 1 d . . . . .
H32 H 0.470695 0.508430 0.094075 0.064 Uiso 1 1 calc R U . . .
C37 C 0.0657(5) 0.9172(3) 0.3263(3) 0.0535(12) Uani 1 1 d . . . . .
C7 C 0.4855(5) 0.0834(4) 0.4272(3) 0.0620(14) Uani 1 1 d . . . . .
H34 H 0.544857 0.047534 0.415358 0.074 Uiso 1 1 calc R U . . .
C63 C 0.9009(5) 0.2400(3) 0.1655(4) 0.0596(14) Uani 1 1 d . . . . .
C47 C 0.8275(5) 0.4253(3) 0.1125(3) 0.0555(13) Uani 1 1 d . . . . .
H36 H 0.912482 0.419892 0.119059 0.067 Uiso 1 1 calc R U . . .
C41 C -0.0863(5) 0.8225(4) 0.3426(3) 0.0593(14) Uani 1 1 d . . . . .
C32 C 0.3949(5) 0.5909(3) 0.2773(3) 0.0548(13) Uani 1 1 d . . . . .
H38 H 0.366858 0.549059 0.223666 0.066 Uiso 1 1 calc R U . . .
C15 C 0.5535(5) 0.0351(3) 0.2245(3) 0.0593(14) Uani 1 1 d . . . . .
C1 C 0.3197(6) 0.3097(3) 0.3057(3) 0.0598(14) Uani 1 1 d . . . . .
C51 C 0.5820(5) 0.1414(3) 0.0529(3) 0.0613(14) Uani 1 1 d . . . . .
H41 H 0.640734 0.105690 0.054842 0.074 Uiso 1 1 calc R U . . .
F2 F 0.1687(4) 0.2217(4) 0.3810(3) 0.1211(17) Uani 1 1 d . . . . .
C25 C 0.2545(5) 0.7740(4) 0.3791(3) 0.0606(14) Uani 1 1 d . . . . .
H43 H 0.245809 0.822814 0.422513 0.073 Uiso 1 1 calc R U . . .
C55 C 0.5873(5) 0.6164(3) 0.1312(3) 0.0573(13) Uani 1 1 d . . . . .
H44 H 0.671724 0.637350 0.139719 0.069 Uiso 1 1 calc R U . . .
C53 C 0.4017(5) 0.1912(3) 0.0397(3) 0.0599(14) Uani 1 1 d . . . . .
H45 H 0.316011 0.194666 0.030716 0.072 Uiso 1 1 calc R U . . .
B3 B 0.4821(5) 0.3465(4) 0.0715(3) 0.0455(13) Uani 1 1 d . . . . .
C24 C 0.3452(5) 0.7262(4) 0.3821(3) 0.0623(15) Uani 1 1 d . . . . .
H47 H 0.409669 0.736073 0.427943 0.075 Uiso 1 1 calc R U . . .
C17 C 0.7708(6) 0.0326(4) 0.2181(4) 0.0660(15) Uani 1 1 d . . . . .
C30 C -0.1054(5) 0.6659(4) 0.0500(3) 0.0592(14) Uani 1 1 d . . . . .
H49 H -0.165684 0.659358 0.003472 0.071 Uiso 1 1 calc R U . . .
C8 C 0.4133(6) 0.0911(4) 0.4823(4) 0.0731(17) Uani 1 1 d . . . . .
H50 H 0.415360 0.061456 0.514094 0.088 Uiso 1 1 calc R U . . .
C38 C 0.0116(5) 0.9852(4) 0.3708(3) 0.0623(14) Uani 1 1 d . . . . .
H51 H 0.045347 1.039949 0.380980 0.075 Uiso 1 1 calc R U . . .
C43 C -0.1470(7) 1.0487(4) 0.4484(4) 0.086(2) Uani 1 1 d . . . . .
H52A H -0.089546 1.100602 0.466323 0.129 Uiso 1 1 calc R U . . .
H52B H -0.162542 1.042902 0.495031 0.129 Uiso 1 1 calc R U . . .
H52C H -0.225266 1.049913 0.414342 0.129 Uiso 1 1 calc R U . . .
C10 C 0.2366(6) 0.3682(4) 0.3259(4) 0.0703(16) Uani 1 1 d . . . . .
H53 H 0.203133 0.376664 0.370083 0.084 Uiso 1 1 calc R U . . .
C3 C 0.4625(6) 0.2373(4) 0.2476(3) 0.0640(15) Uani 1 1 d . . . . .
H54 H 0.517897 0.217119 0.215115 0.077 Uiso 1 1 calc R U . . .
C18 C 0.8056(6) 0.1084(4) 0.2871(3) 0.0635(14) Uani 1 1 d . . . . .
H55 H 0.890557 0.133268 0.307942 0.076 Uiso 1 1 calc R U . . .
C33 C 0.4988(6) 0.5839(4) 0.3256(4) 0.0742(17) Uani 1 1 d . . . . .
H56 H 0.526450 0.626345 0.378932 0.089 Uiso 1 1 calc R U . . .
C46 C 0.7805(5) 0.4962(3) 0.1188(3) 0.0569(13) Uani 1 1 d . . . . .
H57 H 0.826988 0.548185 0.130556 0.068 Uiso 1 1 calc R U . . .
C40 C -0.1366(6) 0.8931(4) 0.3854(3) 0.0679(16) Uani 1 1 d . . . . .
H58 H -0.205305 0.884960 0.405046 0.081 Uiso 1 1 calc R U . . .
C2 C 0.3893(6) 0.2944(4) 0.2453(4) 0.0723(17) Uani 1 1 d . . . . .
H59 H 0.384000 0.320303 0.210040 0.087 Uiso 1 1 calc R U . . .
C39 C -0.0897(6) 0.9743(4) 0.4003(3) 0.0628(15) Uani 1 1 d . . . . .
C16 C 0.6452(6) -0.0034(4) 0.1879(4) 0.0672(15) Uani 1 1 d . . . . .
H61 H 0.620730 -0.055165 0.141493 0.081 Uiso 1 1 calc R U . . .
C56 C 0.5422(7) 0.7619(4) 0.1693(5) 0.085(2) Uani 1 1 d . . . . .
H62A H 0.502018 0.776556 0.125936 0.102 Uiso 1 1 calc R U . . .
H62B H 0.633046 0.776441 0.179722 0.102 Uiso 1 1 calc R U . . .
N3 N 0.1321(6) 0.4726(4) 0.2958(4) 0.1003(19) Uani 1 1 d . . . . .
H7 H 0.111108 0.491711 0.259788 0.120 Uiso 1 1 calc R U . . .
C60 C 0.9856(6) 0.1546(4) 0.0291(5) 0.0798(19) Uani 1 1 d . . . . .
H64 H 1.015415 0.126885 -0.016695 0.096 Uiso 1 1 calc R U . . .
C9 C 0.3393(6) 0.1501(4) 0.4808(3) 0.0688(16) Uani 1 1 d . . . . .
H65 H 0.281325 0.167269 0.511934 0.083 Uiso 1 1 calc R U . . .
C42 C 0.1745(6) 0.9333(4) 0.2941(4) 0.0756(17) Uani 1 1 d . . . . .
H66A H 0.185001 0.991038 0.300940 0.113 Uiso 1 1 calc R U . . .
H66B H 0.157538 0.895260 0.237055 0.113 Uiso 1 1 calc R U . . .
H66C H 0.250456 0.923813 0.323627 0.113 Uiso 1 1 calc R U . . .
C52 C 0.4512(5) 0.1201(3) 0.0353(4) 0.0680(16) Uani 1 1 d . . . . .
H67 H 0.405981 0.067475 0.022904 0.082 Uiso 1 1 calc R U . . .
N6 N 0.5652(5) 0.5214(4) 0.3033(3) 0.100(2) Uani 1 1 d . . . . .
H9 H 0.536565 0.480343 0.255192 0.120 Uiso 1 1 calc R U . . .
C61 C 1.0420(6) 0.1502(4) 0.1005(6) 0.079(2) Uani 1 1 d . . . . .
C20 C 0.4171(6) -0.0048(4) 0.1868(4) 0.0863(19) Uani 1 1 d . . . . .
H70A H 0.384388 -0.019342 0.224537 0.129 Uiso 1 1 calc R U . . .
H70B H 0.409356 -0.055367 0.137483 0.129 Uiso 1 1 calc R U . . .
H70C H 0.370000 0.034629 0.174355 0.129 Uiso 1 1 calc R U . . .
C66 C 0.8569(7) 0.2866(5) 0.2411(4) 0.0841(19) Uani 1 1 d . . . . .
H71A H 0.846862 0.342815 0.246743 0.126 Uiso 1 1 calc R U . . .
H71B H 0.918481 0.290475 0.288176 0.126 Uiso 1 1 calc R U . . .
H71C H 0.777408 0.256317 0.236526 0.126 Uiso 1 1 calc R U . . .
C44 C -0.1388(7) 0.7361(4) 0.3324(5) 0.089(2) Uani 1 1 d . . . . .
H72A H -0.095102 0.726914 0.377995 0.133 Uiso 1 1 calc R U . . .
H72B H -0.127471 0.693339 0.282698 0.133 Uiso 1 1 calc R U . . .
H72C H -0.227331 0.732957 0.330104 0.133 Uiso 1 1 calc R U . . .
C21 C 0.8681(7) -0.0100(5) 0.1750(4) 0.095(2) Uani 1 1 d . . . . .
H73A H 0.864931 -0.066624 0.171272 0.143 Uiso 1 1 calc R U . . .
H73B H 0.950979 0.022251 0.205534 0.143 Uiso 1 1 calc R U . . .
H73C H 0.849841 -0.012682 0.121068 0.143 Uiso 1 1 calc R U . . .
C11 C 0.2047(6) 0.4126(4) 0.2811(4) 0.0791(18) Uani 1 1 d . . . . .
H74 H 0.236842 0.399694 0.235718 0.095 Uiso 1 1 calc R U . . .
C65 C 1.1450(7) 0.0980(5) 0.1058(7) 0.123(3) Uani 1 1 d . . . . .
H75A H 1.216110 0.132699 0.150590 0.184 Uiso 1 1 calc R U . . .
H75B H 1.170679 0.077257 0.055748 0.184 Uiso 1 1 calc R U . . .
H75C H 1.113585 0.050661 0.114407 0.184 Uiso 1 1 calc R U . . .
C62 C 1.0003(6) 0.1952(4) 0.1690(5) 0.0750(17) Uani 1 1 d . . . . .
H76 H 1.039889 0.195453 0.218570 0.090 Uiso 1 1 calc R U . . .
B1 B 0.2984(7) 0.2474(5) 0.4089(4) 0.0677(18) Uani 1 1 d . . . . .
C22 C 0.7603(6) 0.2322(4) 0.4018(4) 0.0750(17) Uani 1 1 d . . . . .
H78A H 0.730947 0.277117 0.389407 0.112 Uiso 1 1 calc R U . . .
H78B H 0.850982 0.243349 0.419758 0.112 Uiso 1 1 calc R U . . .
H78C H 0.726076 0.229191 0.444302 0.112 Uiso 1 1 calc R U . . .
C64 C 0.8260(6) 0.1997(5) -0.0577(4) 0.087(2) Uani 1 1 d . . . . .
H79A H 0.861535 0.162893 -0.099623 0.131 Uiso 1 1 calc R U . . .
H79B H 0.841263 0.256733 -0.052467 0.131 Uiso 1 1 calc R U . . .
H79C H 0.736508 0.180511 -0.072070 0.131 Uiso 1 1 calc R U . . .
C57 C 0.5033(9) 0.8125(5) 0.2442(5) 0.112(3) Uani 1 1 d . . . . .
H80A H 0.413051 0.800101 0.233567 0.168 Uiso 1 1 calc R U . . .
H80B H 0.528786 0.872044 0.260288 0.168 Uiso 1 1 calc R U . . .
H80C H 0.542903 0.798324 0.287350 0.168 Uiso 1 1 calc R U . . .
C34 C 0.6826(11) 0.5166(8) 0.3538(6) 0.159(5) Uani 1 1 d . . . . .
H81 H 0.760858 0.545244 0.359219 0.191 Uiso 1 1 calc R U . . .
C12 C 0.0861(11) 0.5078(7) 0.3687(8) 0.157(5) Uani 1 1 d . U . . .
H85 H 0.084172 0.480237 0.402082 0.189 Uiso 1 1 calc R U . . .
C13 C 0.0462(15) 0.5836(8) 0.3849(10) 0.226(8) Uani 1 1 d . U . . .
H86A H 0.049465 0.609465 0.350198 0.272 Uiso 1 1 calc R U . . .
H86B H 0.015585 0.609740 0.430631 0.272 Uiso 1 1 calc R U . . .
C35 C 0.6678(17) 0.4671(8) 0.3917(9) 0.258(11) Uani 1 1 d . . . . .
H87A H 0.587568 0.439682 0.384421 0.309 Uiso 1 1 calc R U . . .
H87B H 0.737795 0.460217 0.425373 0.309 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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
C31 N5 C28 106.9(4) . . ?
C31 N5 B2 127.3(4) . . ?
C28 N5 B2 125.7(4) . . ?
C45 N7 C48 109.2(4) . . ?
C45 N7 B3 126.4(4) . . ?
C48 N7 B3 124.4(4) . . ?
C53 N8 C50 107.1(4) . . ?
C53 N8 B3 126.9(4) . . ?
C50 N8 B3 125.9(4) . . ?
C23 N4 C26 109.0(4) . . ?
C23 N4 B2 127.6(4) . . ?
C26 N4 B2 123.3(4) . . ?
C1 N1 C4 108.3(4) . . ?
C1 N1 B1 128.5(5) . . ?
C4 N1 B1 123.2(4) . . ?
C48 C49 C50 119.2(4) . . ?
C48 C49 C58 123.9(4) . . ?
C50 C49 C58 117.0(4) . . ?
C9 N2 C6 106.9(4) . . ?
C9 N2 B1 126.4(5) . . ?
C6 N2 B1 126.7(4) . . ?
C29 C28 N5 108.0(4) . . ?
C29 C28 C27 131.6(5) . . ?
N5 C28 C27 120.2(4) . . ?
N8 C50 C51 108.7(4) . . ?
N8 C50 C49 120.5(4) . . ?
C51 C50 C49 130.8(5) . . ?
C63 C58 C59 119.8(5) . . ?
C63 C58 C49 119.6(5) . . ?
C59 C58 C49 120.3(5) . . ?
C37 C36 C41 120.3(4) . . ?
C37 C36 C27 120.3(4) . . ?
C41 C36 C27 119.3(5) . . ?
C15 C14 C19 120.3(5) . . ?
C15 C14 C5 119.7(5) . . ?
C19 C14 C5 119.8(4) . . ?
N4 C23 C32 123.3(4) . . ?
N4 C23 C24 108.0(4) . . ?
C32 C23 C24 128.7(5) . . ?
N7 C45 C54 123.4(4) . . ?
N7 C45 C46 107.3(4) . . ?
C54 C45 C46 129.2(4) . . ?
C26 C27 C28 119.9(4) . . ?
C26 C27 C36 121.6(4) . . ?
C28 C27 C36 118.5(4) . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 C14 119.0(4) . . ?
C6 C5 C14 120.9(4) . . ?
C27 C26 N4 122.3(4) . . ?
C27 C26 C25 131.2(5) . . ?
N4 C26 C25 106.4(4) . . ?
C18 C19 C14 118.4(5) . . ?
C18 C19 C22 120.2(5) . . ?
C14 C19 C22 121.4(5) . . ?
C28 C29 C30 107.8(5) . . ?
C7 C6 N2 108.3(4) . . ?
C7 C6 C5 132.3(5) . . ?
N2 C6 C5 119.4(4) . . ?
C49 C48 N7 122.6(4) . . ?
C49 C48 C47 130.5(5) . . ?
N7 C48 C47 106.9(4) . . ?
C5 C4 N1 123.0(4) . . ?
C5 C4 C3 129.8(5) . . ?
N1 C4 C3 107.2(4) . . ?
F4 B2 F3 107.7(4) . . ?
F4 B2 N5 110.4(4) . . ?
F3 B2 N5 111.7(4) . . ?
F4 B2 N4 110.5(4) . . ?
F3 B2 N4 108.9(4) . . ?
N5 B2 N4 107.7(4) . . ?
C55 N9 C56 125.8(5) . . ?
N5 C31 C30 110.7(5) . . ?
C60 C59 C58 118.4(6) . . ?
C60 C59 C64 121.0(6) . . ?
C58 C59 C64 120.5(5) . . ?
C55 C54 C45 123.3(5) . . ?
C36 C37 C38 118.7(5) . . ?
C36 C37 C42 121.7(4) . . ?
C38 C37 C42 119.6(5) . . ?
C6 C7 C8 107.4(5) . . ?
C62 C63 C58 119.3(6) . . ?
C62 C63 C66 120.0(6) . . ?
C58 C63 C66 120.8(5) . . ?
C46 C47 C48 108.6(4) . . ?
C40 C41 C36 117.9(5) . . ?
C40 C41 C44 119.9(5) . . ?
C36 C41 C44 122.1(5) . . ?
C33 C32 C23 123.8(5) . . ?
C16 C15 C14 118.8(5) . . ?
C16 C15 C20 119.8(5) . . ?
C14 C15 C20 121.3(5) . . ?
N1 C1 C10 125.0(5) . . ?
N1 C1 C2 107.6(5) . . ?
C10 C1 C2 127.4(5) . . ?
C50 C51 C52 107.1(5) . . ?
C24 C25 C26 108.2(5) . . ?
N9 C55 C54 125.6(5) . . ?
N8 C53 C52 110.0(5) . . ?
F5 B3 F6 106.8(4) . . ?
F5 B3 N8 110.9(4) . . ?
F6 B3 N8 110.6(4) . . ?
F5 B3 N7 112.3(4) . . ?
F6 B3 N7 108.9(4) . . ?
N8 B3 N7 107.4(4) . . ?
C25 C24 C23 108.4(4) . . ?
C18 C17 C16 118.4(5) . . ?
C18 C17 C21 121.0(6) . . ?
C16 C17 C21 120.6(6) . . ?
C31 C30 C29 106.5(4) . . ?
C9 C8 C7 107.1(5) . . ?
C39 C38 C37 122.3(5) . . ?
C11 C10 C1 120.4(6) . . ?
C2 C3 C4 107.9(5) . . ?
C17 C18 C19 122.1(6) . . ?
N6 C33 C32 125.1(5) . . ?
C47 C46 C45 108.0(4) . . ?
C39 C40 C41 123.1(5) . . ?
C3 C2 C1 109.1(5) . . ?
C40 C39 C38 117.8(5) . . ?
C40 C39 C43 120.7(6) . . ?
C38 C39 C43 121.5(6) . . ?
C17 C16 C15 122.0(5) . . ?
N9 C56 C57 112.3(6) . . ?
C11 N3 C12 124.2(6) . . ?
C61 C60 C59 122.9(6) . . ?
N2 C9 C8 110.3(5) . . ?
C53 C52 C51 107.0(5) . . ?
C33 N6 C34 125.2(6) . . ?
C60 C61 C62 117.6(6) . . ?
C60 C61 C65 122.4(8) . . ?
C62 C61 C65 120.0(8) . . ?
N3 C11 C10 126.6(7) . . ?
C61 C62 C63 121.8(6) . . ?
F1 B1 F2 108.4(6) . . ?
F1 B1 N2 109.9(5) . . ?
F2 B1 N2 110.5(5) . . ?
F1 B1 N1 110.4(5) . . ?
F2 B1 N1 110.1(5) . . ?
N2 B1 N1 107.6(5) . . ?
C35 C34 N6 113.9(13) . . ?
C13 C12 N3 115.6(10) . . ?
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
F6 B3 1.411(6) . ?
F4 B2 1.390(6) . ?
F5 B3 1.366(6) . ?
F3 B2 1.396(6) . ?
N5 C31 1.347(6) . ?
N5 C28 1.388(6) . ?
N5 B2 1.511(7) . ?
N7 C45 1.358(6) . ?
N7 C48 1.399(6) . ?
N7 B3 1.531(6) . ?
N8 C53 1.358(6) . ?
N8 C50 1.376(6) . ?
N8 B3 1.525(7) . ?
N4 C23 1.345(6) . ?
N4 C26 1.407(6) . ?
N4 B2 1.546(6) . ?
N1 C1 1.351(6) . ?
N1 C4 1.406(6) . ?
N1 B1 1.538(7) . ?
C49 C48 1.358(6) . ?
C49 C50 1.432(6) . ?
C49 C58 1.482(7) . ?
N2 C9 1.351(6) . ?
N2 C6 1.386(6) . ?
N2 B1 1.519(8) . ?
F1 B1 1.367(8) . ?
C28 C29 1.378(7) . ?
C28 C27 1.419(7) . ?
C50 C51 1.380(7) . ?
C58 C63 1.390(7) . ?
C58 C59 1.403(7) . ?
C36 C37 1.391(7) . ?
C36 C41 1.403(7) . ?
C36 C27 1.491(6) . ?
C14 C15 1.391(7) . ?
C14 C19 1.394(7) . ?
C14 C5 1.494(7) . ?
C23 C32 1.406(7) . ?
C23 C24 1.425(7) . ?
C45 C54 1.388(7) . ?
C45 C46 1.451(7) . ?
C27 C26 1.363(7) . ?
C5 C4 1.356(7) . ?
C5 C6 1.419(7) . ?
C26 C25 1.422(7) . ?
C19 C18 1.393(7) . ?
C19 C22 1.496(8) . ?
C29 C30 1.386(7) . ?
C6 C7 1.374(7) . ?
C48 C47 1.429(6) . ?
C4 C3 1.423(7) . ?
N9 C55 1.311(7) . ?
N9 C56 1.449(7) . ?
C31 C30 1.368(7) . ?
C59 C60 1.379(8) . ?
C59 C64 1.506(8) . ?
C54 C55 1.362(7) . ?
C37 C38 1.392(7) . ?
C37 C42 1.503(7) . ?
C7 C8 1.389(8) . ?
C63 C62 1.388(8) . ?
C63 C66 1.504(8) . ?
C47 C46 1.342(7) . ?
C41 C40 1.388(7) . ?
C41 C44 1.501(8) . ?
C32 C33 1.340(7) . ?
C15 C16 1.388(8) . ?
C15 C20 1.496(8) . ?
C1 C10 1.401(8) . ?
C1 C2 1.432(8) . ?
C51 C52 1.393(8) . ?
F2 B1 1.382(8) . ?
C25 C24 1.347(7) . ?
C53 C52 1.365(8) . ?
C17 C18 1.372(8) . ?
C17 C16 1.372(8) . ?
C17 C21 1.518(8) . ?
C8 C9 1.358(8) . ?
C38 C39 1.372(8) . ?
C43 C39 1.508(7) . ?
C10 C11 1.362(8) . ?
C3 C2 1.329(8) . ?
C33 N6 1.325(7) . ?
C40 C39 1.371(8) . ?
C56 C57 1.479(10) . ?
N3 C11 1.331(8) . ?
N3 C12 1.453(11) . ?
C60 C61 1.374(10) . ?
N6 C34 1.452(10) . ?
C61 C62 1.384(9) . ?
C61 C65 1.509(9) . ?
C34 C35 1.342(18) . ?
C12 C13 1.357(13) . ?
