#------------------------------------------------------------------------------
#$Date: 2026-03-27 00:02:05 +0100 (Fri 27 de Mar de 2026) $
#$Revision: 305186 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/56/7135663.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_7135663
loop_
_publ_author_name
'Wüst, Leonie'
'Wellnitz, Tim'
'Radacki, Krzysztof'
'Nees, Samuel'
'Braunschweig, Holger'
_publ_section_title
;
 Attempted halogenation of ambiphilic 1,2,3-benzodiazaborines: Balancing
 Lewis acidity and Lewis basicity
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D6CC01072E
_journal_year                    2026
_chemical_formula_moiety         'C26 H18 B4 Br4 N4 O, C7 H8'
_chemical_formula_sum            'C33 H26 B4 Br4 N4 O'
_chemical_formula_weight         857.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2026-02-03
_audit_creation_method           'CIF-fill 1.6l (K.Radacki, 2005-26)'
_audit_update_record
;
2026-02-15 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.103(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4361(7)
_cell_length_b                   15.706(10)
_cell_length_c                   16.2368(9)
_cell_measurement_reflns_used    21103
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.7090
_cell_measurement_theta_min      2.7470
_cell_volume                     3413(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2025/1 (Sheldrick, 2025)'
_computing_structure_refinement  'SHELXL-2025/1 (Sheldrick, 2025)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)''
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 HPA
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HyPix Arc150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
 
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     28.00 100.00   0.50    0.05    --   71.48-126.00-150.00  144
  2  ω     27.00  74.00   0.50    0.05    --   65.06 -95.00-150.00   94
  3  ω     27.00  74.00   0.50    0.05    --   65.06 -95.00-120.00   94
  4  ω     39.00  85.00   0.50    0.05    --   76.67 -95.00-150.00   92
  5  ω     34.00  80.00   0.50    0.05    --   71.48 -95.00 -90.00   92
  6  ω     39.00  85.00   0.50    0.05    --   76.67 -95.00  60.00   92
  7  ω     27.00  74.00   0.50    0.05    --   65.06 -95.00 150.00   94
  8  ω   -102.00 -28.00   0.50    0.05    --  -65.03   0.00-120.00  148
  9  ω   -102.00 -30.00   0.50    0.05    --  -73.64 126.00 -60.00  144
 10  ω    -94.00 -21.00   0.50    0.05    --  -65.03 126.00 -30.00  146
 11  ω   -105.00 -32.00   0.50    0.05    --  -75.71 126.00  60.00  146
 12  ω   -110.00 -34.00   0.50    0.05    --  -65.03 -15.00 120.00  152
 13  ω   -119.00 -83.00   0.50    0.05    --  -73.64 -15.00  60.00   72
 14  ω   -110.00 -34.00   0.50    0.05    --  -65.03 -15.00-120.00  152
 15  ω   -110.00 -34.00   0.50    0.05    --  -65.03 -15.00-180.00  152
 16  ω   -119.00 -73.00   0.50    0.05    --  -75.71-126.00 -60.00   92
 17  ω   -119.00 -73.00   0.50    0.05    --  -75.71-126.00-120.00   92
 18  ω   -119.00 -73.00   0.50    0.05    --  -75.71-126.00 -30.00   92
 19  ω   -119.00 -73.00   0.50    0.05    --  -75.71-126.00  90.00   92
 20  ω   -119.00 -73.00   0.50    0.05    --  -75.71-126.00 120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0679391000
_diffrn_orient_matrix_UB_12      -0.0785359000
_diffrn_orient_matrix_UB_13      0.0049560000
_diffrn_orient_matrix_UB_21      0.0034167000
_diffrn_orient_matrix_UB_22      -0.0147996000
_diffrn_orient_matrix_UB_23      -0.0934866000
_diffrn_orient_matrix_UB_31      0.0928849000
_diffrn_orient_matrix_UB_32      -0.0568621000
_diffrn_orient_matrix_UB_33      0.0175406000
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34131
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.458
_diffrn_reflns_theta_min         3.302
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    6.018
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_preparation
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         6648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0382P)²+6.0138P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5906
_reflns_number_total             6648
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6cc01072e2.cif
_cod_data_source_block           CH_borylated_BOB_anhydride
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7135663
_shelx_shelxl_version_number     2025/1
_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   0.265
_shelx_estimated_absorpt_t_max   0.508
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.14011(2) 0.27103(2) 0.55611(2) 0.03060(9) Uani 1 1 d . . . . .
C1 C 0.2981(2) 0.4233(2) 0.50082(19) 0.0242(6) Uani 1 1 d . . . . .
H1 H 0.319955 0.365765 0.503794 0.029 Uiso 1 1 calc R U . . .
N1 N 0.18242(17) 0.52618(15) 0.53734(15) 0.0194(5) Uani 1 1 d . . . . .
B1 B 0.2308(2) 0.5935(2) 0.4968(2) 0.0211(7) Uani 1 1 d . . . . .
C14 C 0.3460(2) 0.90425(19) 0.48641(18) 0.0213(6) Uani 1 1 d . . . . .
H14 H 0.386470 0.953110 0.480700 0.026 Uiso 1 1 calc R U . . .
O1 O 0.19248(14) 0.67358(13) 0.50079(13) 0.0214(4) Uani 1 1 d . . . . .
N2 N 0.22188(18) 0.44443(15) 0.54003(15) 0.0209(5) Uani 1 1 d . . . . .
B2 B 0.1665(3) 0.3873(2) 0.6032(2) 0.0241(7) Uani 1 1 d . . . . .
C15 C 0.2528(2) 0.89899(19) 0.43663(18) 0.0210(6) Uani 1 1 d . . . . .
C2 C 0.3510(2) 0.4821(2) 0.45320(18) 0.0230(6) Uani 1 1 d . . . . .
Br2 Br 0.26267(2) 0.37989(2) 0.70735(2) 0.03170(10) Uani 1 1 d . . . . .
C17 C 0.1073(2) 0.8172(2) 0.38758(19) 0.0252(6) Uani 1 1 d . . . . .
H17 H 0.068948 0.766407 0.386974 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4329(2) 0.4537(2) 0.41270(19) 0.0272(7) Uani 1 1 d . . . . .
H7 H 0.451116 0.395213 0.414178 0.033 Uiso 1 1 calc R U . . .
B3 B 0.2362(2) 0.7528(2) 0.4980(2) 0.0202(7) Uani 1 1 d . . . . .
N3 N 0.32278(17) 0.77351(15) 0.55226(15) 0.0182(5) Uani 1 1 d . . . . .
Br3 Br 0.51064(2) 0.95531(2) 0.64695(2) 0.02394(9) Uani 1 1 d . . . . .
C3 C 0.3224(2) 0.5684(2) 0.45089(18) 0.0218(6) Uani 1 1 d . . . . .
C16 C 0.1972(2) 0.8229(2) 0.43805(18) 0.0213(6) Uani 1 1 d . . . . .
C18 C 0.0743(2) 0.8853(2) 0.3387(2) 0.0317(7) Uani 1 1 d . . . . .
H18 H 0.012745 0.881035 0.305270 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4866(2) 0.5115(2) 0.37081(19) 0.0284(7) Uani 1 1 d . . . . .
H6 H 0.542419 0.492949 0.343540 0.034 Uiso 1 1 calc R U . . .
B4 B 0.4836(2) 0.8423(2) 0.5922(2) 0.0209(7) Uani 1 1 d . . . . .
N4 N 0.37834(17) 0.84611(15) 0.53888(15) 0.0185(5) Uani 1 1 d . . . . .
Br4 Br 0.58937(2) 0.81708(2) 0.51330(2) 0.02759(9) Uani 1 1 d . . . . .
C4 C 0.3784(2) 0.6253(2) 0.40705(18) 0.0231(6) Uani 1 1 d . . . . .
H4 H 0.360405 0.683800 0.404059 0.028 Uiso 1 1 calc R U . . .
C20 C 0.2188(2) 0.9675(2) 0.38610(19) 0.0254(6) Uani 1 1 d . . . . .
H20 H 0.256738 1.018503 0.385278 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1298(2) 0.9598(2) 0.3378(2) 0.0303(7) Uani 1 1 d . . . . .
H19 H 0.106064 1.005874 0.303561 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4595(2) 0.5970(2) 0.36823(19) 0.0281(7) Uani 1 1 d . . . . .
H5 H 0.497289 0.636374 0.339372 0.034 Uiso 1 1 calc R U . . .
C22 C 0.3253(2) 0.66719(19) 0.66727(18) 0.0217(6) Uani 1 1 d . . . . .
H22 H 0.261531 0.644847 0.648536 0.026 Uiso 1 1 calc R U . . .
C9 C 0.0288(2) 0.5946(2) 0.58292(19) 0.0233(6) Uani 1 1 d . . . . .
H9 H 0.042315 0.647400 0.557639 0.028 Uiso 1 1 calc R U . . .
C21 C 0.3694(2) 0.73143(18) 0.62429(17) 0.0190(6) Uani 1 1 d . . . . .
C8 C 0.0931(2) 0.52605(19) 0.57959(18) 0.0204(6) Uani 1 1 d . . . . .
C13 C 0.0760(2) 0.4474(2) 0.61581(18) 0.0222(6) Uani 1 1 d . . . . .
C25 C 0.5138(2) 0.7342(2) 0.72174(19) 0.0244(6) Uani 1 1 d . . . . .
H25 H 0.577827 0.756109 0.740103 0.029 Uiso 1 1 calc R U . . .
C12 C -0.0100(2) 0.4379(2) 0.65662(19) 0.0251(6) Uani 1 1 d . . . . .
H12 H -0.023754 0.384940 0.681516 0.030 Uiso 1 1 calc R U . . .
C24 C 0.4716(2) 0.6697(2) 0.76606(19) 0.0280(7) Uani 1 1 d . . . . .
H24 H 0.506603 0.647933 0.814984 0.034 Uiso 1 1 calc R U . . .
C11 C -0.0756(2) 0.5052(2) 0.66109(19) 0.0270(7) Uani 1 1 d . . . . .
H11 H -0.134136 0.498350 0.689160 0.032 Uiso 1 1 calc R U . . .
C23 C 0.3780(2) 0.6370(2) 0.73863(19) 0.0252(6) Uani 1 1 d . . . . .
H23 H 0.349780 0.593200 0.769476 0.030 Uiso 1 1 calc R U . . .
C10 C -0.0562(2) 0.5834(2) 0.62459(19) 0.0249(6) Uani 1 1 d . . . . .
H10 H -0.101682 0.629252 0.628290 0.030 Uiso 1 1 calc R U . . .
C26 C 0.4617(2) 0.76667(18) 0.65010(18) 0.0202(6) Uani 1 1 d . . . . .
C1_1 C 0.18049(18) 0.96037(15) 0.63723(15) 0.0386(4) Uiso 0.758(4) 1 d G . P A 1
C2_1 C 0.09135(19) 0.92942(19) 0.59691(17) 0.0386(4) Uiso 0.758(4) 1 d G . P A 1
H2_1 H 0.055983 0.962325 0.554804 0.046 Uiso 0.758(4) 1 calc R U P A 1
C3_1 C 0.05434(19) 0.8500(2) 0.6186(2) 0.0386(4) Uiso 0.758(4) 1 d G . P A 1
H3_1 H -0.006147 0.828959 0.591262 0.046 Uiso 0.758(4) 1 calc R U P A 1
C4_1 C 0.1065(2) 0.80148(16) 0.6807(2) 0.0386(4) Uiso 0.758(4) 1 d G . P A 1
H4_1 H 0.081334 0.747572 0.695425 0.046 Uiso 0.758(4) 1 calc R U P A 1
C5_1 C 0.1956(2) 0.83244(18) 0.72101(19) 0.0386(4) Uiso 0.758(4) 1 d G . P A 1
H5_1 H 0.230945 0.799539 0.763124 0.046 Uiso 0.758(4) 1 calc R U P A 1
C6_1 C 0.23260(19) 0.91188(18) 0.69929(18) 0.0386(4) Uiso 0.758(4) 1 d G . P A 1
H6_1 H 0.293091 0.932888 0.726653 0.046 Uiso 0.758(4) 1 calc R U P A 1
C7_1 C 0.2207(3) 1.04662(18) 0.6136(2) 0.0386(4) Uiso 0.758(4) 1 d G . P A 1
H7A_1 H 0.283139 1.058480 0.647582 0.058 Uiso 0.758(4) 1 calc R U P A 1
H7B_1 H 0.233297 1.046133 0.555120 0.058 Uiso 0.758(4) 1 calc R U P A 1
H7C_1 H 0.171508 1.090866 0.623017 0.058 Uiso 0.758(4) 1 calc R U P A 1
C1_2 C 0.1908(5) 0.9712(5) 0.6433(5) 0.0386(4) Uiso 0.242(4) 1 d G . P A 2
C2_2 C 0.1003(6) 0.9688(6) 0.5934(5) 0.0386(4) Uiso 0.242(4) 1 d G . P A 2
H2_2 H 0.080098 1.016358 0.559841 0.046 Uiso 0.242(4) 1 calc R U P A 2
C3_2 C 0.0397(6) 0.8963(7) 0.5929(6) 0.0386(4) Uiso 0.242(4) 1 d G . P A 2
H3_2 H -0.021672 0.894620 0.559054 0.046 Uiso 0.242(4) 1 calc R U P A 2
C4_2 C 0.0695(7) 0.8262(5) 0.6424(7) 0.0386(4) Uiso 0.242(4) 1 d G . P A 2
H4_2 H 0.028376 0.776968 0.642075 0.046 Uiso 0.242(4) 1 calc R U P A 2
C5_2 C 0.1600(8) 0.8286(5) 0.6923(7) 0.0386(4) Uiso 0.242(4) 1 d G . P A 2
H5_2 H 0.180207 0.781040 0.725846 0.046 Uiso 0.242(4) 1 calc R U P A 2
C6_2 C 0.2206(6) 0.9011(6) 0.6927(6) 0.0386(4) Uiso 0.242(4) 1 d G . P A 2
H6_2 H 0.281985 0.902766 0.726617 0.046 Uiso 0.242(4) 1 calc R U P A 2
C7_2 C 0.2566(8) 1.0500(6) 0.6438(8) 0.0386(4) Uiso 0.242(4) 1 d G . P A 2
H7A_2 H 0.316593 1.041087 0.681762 0.058 Uiso 0.242(4) 1 calc R U P A 2
H7B_2 H 0.276111 1.060298 0.587920 0.058 Uiso 0.242(4) 1 calc R U P A 2
H7C_2 H 0.219588 1.099229 0.662028 0.058 Uiso 0.242(4) 1 calc R U P A 2
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 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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 2 0.1007
2 -2 -1 0.0854
-1 0 -2 0.1201
-2 2 1 0.0772
1 -1 2 0.1044
-1 1 -2 0.1239
-1 0 2 0.1573
1 0 -2 0.1277
-2 1 1 0.0974
0 1 -1 0.1125
-1 -2 1 0.1281
1 2 -1 0.0678
2 1 -1 0.0603
-2 -1 1 0.1152
-2 1 0 0.0681
-1 -2 0 0.1013
1 2 0 0.0304
-2 -1 0 0.0931
2 0 1 0.0746
-1 1 0 0.0528
1 -1 0 0.0870
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
N2 C1 C2 123.5(3) . . ?
N2 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N2 N1 B1 120.6(2) . . ?
N2 N1 C8 108.5(2) . . ?
B1 N1 C8 130.9(3) . . ?
O1 B1 N1 118.1(3) . . ?
O1 B1 C3 125.3(3) . . ?
N1 B1 C3 116.6(3) . . ?
N4 C14 C15 123.8(3) . . ?
N4 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
B1 O1 B3 131.9(2) . . ?
C1 N2 N1 122.5(3) . . ?
C1 N2 B2 127.2(3) . . ?
N1 N2 B2 110.0(2) . . ?
C13 B2 N2 99.0(2) . . ?
C13 B2 Br1 119.1(2) . . ?
N2 B2 Br1 110.2(2) . . ?
C13 B2 Br2 111.6(2) . . ?
N2 B2 Br2 105.56(19) . . ?
Br1 B2 Br2 110.07(17) . . ?
C20 C15 C16 120.9(3) . . ?
C20 C15 C14 120.6(3) . . ?
C16 C15 C14 118.5(3) . . ?
C7 C2 C3 121.1(3) . . ?
C7 C2 C1 119.7(3) . . ?
C3 C2 C1 119.1(3) . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C6 C7 C2 119.3(3) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
O1 B3 N3 120.6(3) . . ?
O1 B3 C16 123.1(3) . . ?
N3 B3 C16 116.2(3) . . ?
N4 N3 B3 120.5(2) . . ?
N4 N3 C21 107.6(2) . . ?
B3 N3 C21 131.9(3) . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 B1 124.7(3) . . ?
C2 C3 B1 117.4(3) . . ?
C17 C16 C15 118.3(3) . . ?
C17 C16 B3 123.7(3) . . ?
C15 C16 B3 117.9(3) . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C26 B4 N4 98.6(2) . . ?
C26 B4 Br3 116.3(2) . . ?
N4 B4 Br3 109.0(2) . . ?
C26 B4 Br4 114.3(2) . . ?
N4 B4 Br4 107.6(2) . . ?
Br3 B4 Br4 110.07(16) . . ?
C14 N4 N3 121.8(2) . . ?
C14 N4 B4 127.8(2) . . ?
N3 N4 B4 110.4(2) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C19 C20 C15 119.1(3) . . ?
C19 C20 H20 120.4 . . ?
C15 C20 H20 120.4 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C23 C22 C21 117.3(3) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C8 C9 C10 117.6(3) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C26 C21 C22 123.2(3) . . ?
C26 C21 N3 112.0(2) . . ?
C22 C21 N3 124.6(3) . . ?
C9 C8 C13 123.1(3) . . ?
C9 C8 N1 124.7(3) . . ?
C13 C8 N1 112.2(3) . . ?
C12 C13 C8 118.0(3) . . ?
C12 C13 B2 133.3(3) . . ?
C8 C13 B2 108.6(3) . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C22 C23 C24 121.4(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C21 C26 C25 118.2(3) . . ?
C21 C26 B4 109.5(3) . . ?
C25 C26 B4 132.2(3) . . ?
C2_1 C1_1 C6_1 120.0 . . ?
C2_1 C1_1 C7_1 120.0 . . ?
C6_1 C1_1 C7_1 120.0 . . ?
C1_1 C2_1 C3_1 120.0 . . ?
C1_1 C2_1 H2_1 120.0 . . ?
C3_1 C2_1 H2_1 120.0 . . ?
C4_1 C3_1 C2_1 120.0 . . ?
C4_1 C3_1 H3_1 120.0 . . ?
C2_1 C3_1 H3_1 120.0 . . ?
C5_1 C4_1 C3_1 120.0 . . ?
C5_1 C4_1 H4_1 120.0 . . ?
C3_1 C4_1 H4_1 120.0 . . ?
C4_1 C5_1 C6_1 120.0 . . ?
C4_1 C5_1 H5_1 120.0 . . ?
C6_1 C5_1 H5_1 120.0 . . ?
C5_1 C6_1 C1_1 120.0 . . ?
C5_1 C6_1 H6_1 120.0 . . ?
C1_1 C6_1 H6_1 120.0 . . ?
C1_1 C7_1 H7A_1 109.5 . . ?
C1_1 C7_1 H7B_1 109.5 . . ?
H7A_1 C7_1 H7B_1 109.5 . . ?
C1_1 C7_1 H7C_1 109.5 . . ?
H7A_1 C7_1 H7C_1 109.5 . . ?
H7B_1 C7_1 H7C_1 109.5 . . ?
C2_2 C1_2 C6_2 120.0 . . ?
C2_2 C1_2 C7_2 120.0 . . ?
C6_2 C1_2 C7_2 120.0 . . ?
C1_2 C2_2 C3_2 120.0 . . ?
C1_2 C2_2 H2_2 120.0 . . ?
C3_2 C2_2 H2_2 120.0 . . ?
C4_2 C3_2 C2_2 120.0 . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C5_2 C4_2 C3_2 120.0 . . ?
C5_2 C4_2 H4_2 120.0 . . ?
C3_2 C4_2 H4_2 120.0 . . ?
C4_2 C5_2 C6_2 120.0 . . ?
C4_2 C5_2 H5_2 120.0 . . ?
C6_2 C5_2 H5_2 120.0 . . ?
C5_2 C6_2 C1_2 120.0 . . ?
C5_2 C6_2 H6_2 120.0 . . ?
C1_2 C6_2 H6_2 120.0 . . ?
C1_2 C7_2 H7A_2 109.5 . . ?
C1_2 C7_2 H7B_2 109.5 . . ?
H7A_2 C7_2 H7B_2 109.5 . . ?
C1_2 C7_2 H7C_2 109.5 . . ?
H7A_2 C7_2 H7C_2 109.5 . . ?
H7B_2 C7_2 H7C_2 109.5 . . ?
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
Br1 B2 1.999(4) . ?
C1 N2 1.296(4) . ?
C1 C2 1.434(4) . ?
C1 H1 0.9500 . ?
N1 N2 1.388(3) . ?
N1 B1 1.432(4) . ?
N1 C8 1.435(4) . ?
B1 O1 1.363(4) . ?
B1 C3 1.545(4) . ?
C14 N4 1.297(4) . ?
C14 C15 1.431(4) . ?
C14 H14 0.9500 . ?
O1 B3 1.379(4) . ?
N2 B2 1.596(4) . ?
B2 C13 1.567(5) . ?
B2 Br2 2.038(3) . ?
C15 C20 1.405(4) . ?
C15 C16 1.411(4) . ?
C2 C7 1.404(4) . ?
C2 C3 1.410(4) . ?
C17 C18 1.380(5) . ?
C17 C16 1.401(4) . ?
C17 H17 0.9500 . ?
C7 C6 1.376(5) . ?
C7 H7 0.9500 . ?
B3 N3 1.432(4) . ?
B3 C16 1.531(5) . ?
N3 N4 1.391(3) . ?
N3 C21 1.438(4) . ?
Br3 B4 2.004(4) . ?
C3 C4 1.402(4) . ?
C18 C19 1.389(5) . ?
C18 H18 0.9500 . ?
C6 C5 1.391(5) . ?
C6 H6 0.9500 . ?
B4 C26 1.560(4) . ?
B4 N4 1.593(4) . ?
B4 Br4 2.034(3) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C20 C19 1.376(4) . ?
C20 H20 0.9500 . ?
C19 H19 0.9500 . ?
C5 H5 0.9500 . ?
C22 C23 1.387(4) . ?
C22 C21 1.390(4) . ?
C22 H22 0.9500 . ?
C9 C8 1.384(4) . ?
C9 C10 1.390(4) . ?
C9 H9 0.9500 . ?
C21 C26 1.388(4) . ?
C8 C13 1.396(4) . ?
C13 C12 1.390(4) . ?
C25 C24 1.392(5) . ?
C25 C26 1.399(4) . ?
C25 H25 0.9500 . ?
C12 C11 1.383(5) . ?
C12 H12 0.9500 . ?
C24 C23 1.394(5) . ?
C24 H24 0.9500 . ?
C11 C10 1.397(5) . ?
C11 H11 0.9500 . ?
C23 H23 0.9500 . ?
C10 H10 0.9500 . ?
C1_1 C2_1 1.4000 . ?
C1_1 C6_1 1.4000 . ?
C1_1 C7_1 1.5199 . ?
C2_1 C3_1 1.4001 . ?
C2_1 H2_1 0.9500 . ?
C3_1 C4_1 1.4000 . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.4000 . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.4000 . ?
C5_1 H5_1 0.9500 . ?
C6_1 H6_1 0.9500 . ?
C7_1 H7A_1 0.9800 . ?
C7_1 H7B_1 0.9800 . ?
C7_1 H7C_1 0.9800 . ?
C1_2 C2_2 1.4000 . ?
C1_2 C6_2 1.4000 . ?
C1_2 C7_2 1.5200 . ?
C2_2 C3_2 1.4000 . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.4000 . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.4000 . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.4000 . ?
C5_2 H5_2 0.9500 . ?
C6_2 H6_2 0.9500 . ?
C7_2 H7A_2 0.9800 . ?
C7_2 H7B_2 0.9800 . ?
C7_2 H7C_2 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 B1 O1 -175.8(2) . . . . ?
C8 N1 B1 O1 4.3(5) . . . . ?
N2 N1 B1 C3 5.0(4) . . . . ?
C8 N1 B1 C3 -174.9(3) . . . . ?
N1 B1 O1 B3 152.0(3) . . . . ?
C3 B1 O1 B3 -28.9(5) . . . . ?
C2 C1 N2 N1 2.1(4) . . . . ?
C2 C1 N2 B2 -171.8(3) . . . . ?
B1 N1 N2 C1 -6.0(4) . . . . ?
C8 N1 N2 C1 173.9(3) . . . . ?
B1 N1 N2 B2 168.8(3) . . . . ?
C8 N1 N2 B2 -11.2(3) . . . . ?
C1 N2 B2 C13 -172.7(3) . . . . ?
N1 N2 B2 C13 12.8(3) . . . . ?
C1 N2 B2 Br1 -47.0(4) . . . . ?
N1 N2 B2 Br1 138.5(2) . . . . ?
C1 N2 B2 Br2 71.8(3) . . . . ?
N1 N2 B2 Br2 -102.7(2) . . . . ?
N4 C14 C15 C20 174.7(3) . . . . ?
N4 C14 C15 C16 -6.7(5) . . . . ?
N2 C1 C2 C7 180.0(3) . . . . ?
N2 C1 C2 C3 2.7(5) . . . . ?
C3 C2 C7 C6 0.7(5) . . . . ?
C1 C2 C7 C6 -176.5(3) . . . . ?
B1 O1 B3 N3 -52.3(5) . . . . ?
B1 O1 B3 C16 127.3(3) . . . . ?
O1 B3 N3 N4 167.2(2) . . . . ?
C16 B3 N3 N4 -12.5(4) . . . . ?
O1 B3 N3 C21 -12.5(5) . . . . ?
C16 B3 N3 C21 167.8(3) . . . . ?
C7 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 177.1(3) . . . . ?
C7 C2 C3 B1 179.6(3) . . . . ?
C1 C2 C3 B1 -3.2(4) . . . . ?
O1 B1 C3 C4 0.1(5) . . . . ?
N1 B1 C3 C4 179.2(3) . . . . ?
O1 B1 C3 C2 -179.7(3) . . . . ?
N1 B1 C3 C2 -0.5(4) . . . . ?
C18 C17 C16 C15 -0.7(5) . . . . ?
C18 C17 C16 B3 176.1(3) . . . . ?
C20 C15 C16 C17 0.2(4) . . . . ?
C14 C15 C16 C17 -178.4(3) . . . . ?
C20 C15 C16 B3 -176.9(3) . . . . ?
C14 C15 C16 B3 4.6(4) . . . . ?
O1 B3 C16 C17 7.9(5) . . . . ?
N3 B3 C16 C17 -172.4(3) . . . . ?
O1 B3 C16 C15 -175.2(3) . . . . ?
N3 B3 C16 C15 4.5(4) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C2 C7 C6 C5 -0.4(5) . . . . ?
C15 C14 N4 N3 -1.4(4) . . . . ?
C15 C14 N4 B4 175.1(3) . . . . ?
B3 N3 N4 C14 11.4(4) . . . . ?
C21 N3 N4 C14 -168.8(3) . . . . ?
B3 N3 N4 B4 -165.6(3) . . . . ?
C21 N3 N4 B4 14.2(3) . . . . ?
C26 B4 N4 C14 170.4(3) . . . . ?
Br3 B4 N4 C14 48.6(4) . . . . ?
Br4 B4 N4 C14 -70.7(3) . . . . ?
C26 B4 N4 N3 -12.8(3) . . . . ?
Br3 B4 N4 N3 -134.6(2) . . . . ?
Br4 B4 N4 N3 106.1(2) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
B1 C3 C4 C5 179.7(3) . . . . ?
C16 C15 C20 C19 0.3(5) . . . . ?
C14 C15 C20 C19 178.8(3) . . . . ?
C15 C20 C19 C18 -0.2(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C7 C6 C5 C4 -0.3(5) . . . . ?
C23 C22 C21 C26 -0.9(4) . . . . ?
C23 C22 C21 N3 -176.0(3) . . . . ?
N4 N3 C21 C26 -9.6(3) . . . . ?
B3 N3 C21 C26 170.2(3) . . . . ?
N4 N3 C21 C22 166.0(3) . . . . ?
B3 N3 C21 C22 -14.3(5) . . . . ?
C10 C9 C8 C13 0.1(4) . . . . ?
C10 C9 C8 N1 178.2(3) . . . . ?
N2 N1 C8 C9 -173.9(3) . . . . ?
B1 N1 C8 C9 6.1(5) . . . . ?
N2 N1 C8 C13 4.5(3) . . . . ?
B1 N1 C8 C13 -175.6(3) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
N1 C8 C13 C12 -178.0(3) . . . . ?
C9 C8 C13 B2 -177.3(3) . . . . ?
N1 C8 C13 B2 4.3(3) . . . . ?
N2 B2 C13 C12 173.0(3) . . . . ?
Br1 B2 C13 C12 53.8(4) . . . . ?
Br2 B2 C13 C12 -76.2(4) . . . . ?
N2 B2 C13 C8 -9.9(3) . . . . ?
Br1 B2 C13 C8 -129.1(2) . . . . ?
Br2 B2 C13 C8 100.9(3) . . . . ?
C8 C13 C12 C11 -0.4(4) . . . . ?
B2 C13 C12 C11 176.5(3) . . . . ?
C26 C25 C24 C23 0.6(5) . . . . ?
C13 C12 C11 C10 0.1(5) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C25 C24 C23 C22 0.3(5) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C12 C11 C10 C9 0.3(5) . . . . ?
C22 C21 C26 C25 1.8(4) . . . . ?
N3 C21 C26 C25 177.4(3) . . . . ?
C22 C21 C26 B4 -174.8(3) . . . . ?
N3 C21 C26 B4 0.9(3) . . . . ?
C24 C25 C26 C21 -1.5(4) . . . . ?
C24 C25 C26 B4 174.0(3) . . . . ?
N4 B4 C26 C21 6.8(3) . . . . ?
Br3 B4 C26 C21 123.1(2) . . . . ?
Br4 B4 C26 C21 -106.9(3) . . . . ?
N4 B4 C26 C25 -169.0(3) . . . . ?
Br3 B4 C26 C25 -52.8(4) . . . . ?
Br4 B4 C26 C25 77.2(4) . . . . ?
C6_1 C1_1 C2_1 C3_1 0.0 . . . . ?
C7_1 C1_1 C2_1 C3_1 180.0 . . . . ?
C1_1 C2_1 C3_1 C4_1 0.0 . . . . ?
C2_1 C3_1 C4_1 C5_1 0.0 . . . . ?
C3_1 C4_1 C5_1 C6_1 0.0 . . . . ?
C4_1 C5_1 C6_1 C1_1 0.0 . . . . ?
C2_1 C1_1 C6_1 C5_1 0.0 . . . . ?
C7_1 C1_1 C6_1 C5_1 180.0 . . . . ?
C6_2 C1_2 C2_2 C3_2 0.0 . . . . ?
C7_2 C1_2 C2_2 C3_2 180.0 . . . . ?
C1_2 C2_2 C3_2 C4_2 0.0 . . . . ?
C2_2 C3_2 C4_2 C5_2 0.0 . . . . ?
C3_2 C4_2 C5_2 C6_2 0.0 . . . . ?
C4_2 C5_2 C6_2 C1_2 0.0 . . . . ?
C2_2 C1_2 C6_2 C5_2 0.0 . . . . ?
C7_2 C1_2 C6_2 C5_2 180.0 . . . . ?
