Attempted halogenation of ambiphilic 1,2,3-benzodiazaborines: Balancing Lewis acidity and Lewis basicity
Wüst, Leonie; Wellnitz, Tim; Radacki, Krzysztof; Nees, Samuel; Braunschweig, Holger; Chemical Communications  (2026) –; doi:10.1039/D6CC01072E

data_7135663
_publ_section_title
;
 Attempted halogenation of ambiphilic 1,2,3-benzodiazaborines: balancing
 Lewis acidity and Lewis basicity.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7984
_journal_page_last               7988
_journal_paper_doi               10.1039/d6cc01072e
_journal_volume                  62
_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  \w     28.00 100.00   0.50    0.05    --   71.48-126.00-150.00  144
  2  \w     27.00  74.00   0.50    0.05    --   65.06 -95.00-150.00   94
  3  \w     27.00  74.00   0.50    0.05    --   65.06 -95.00-120.00   94
  4  \w     39.00  85.00   0.50    0.05    --   76.67 -95.00-150.00   92
  5  \w     34.00  80.00   0.50    0.05    --   71.48 -95.00 -90.00   92
  6  \w     39.00  85.00   0.50    0.05    --   76.67 -95.00  60.00   92
  7  \w     27.00  74.00   0.50    0.05    --   65.06 -95.00 150.00   94
  8  \w   -102.00 -28.00   0.50    0.05    --  -65.03   0.00-120.00  148
  9  \w   -102.00 -30.00   0.50    0.05    --  -73.64 126.00 -60.00  144
 10  \w    -94.00 -21.00   0.50    0.05    --  -65.03 126.00 -30.00  146
 11  \w   -105.00 -32.00   0.50    0.05    --  -75.71 126.00  60.00  146
 12  \w   -110.00 -34.00   0.50    0.05    --  -65.03 -15.00 120.00  152
 13  \w   -119.00 -83.00   0.50    0.05    --  -73.64 -15.00  60.00   72
 14  \w   -110.00 -34.00   0.50    0.05    --  -65.03 -15.00-120.00  152
 15  \w   -110.00 -34.00   0.50    0.05    --  -65.03 -15.00-180.00  152
 16  \w   -119.00 -73.00   0.50    0.05    --  -75.71-126.00 -60.00   92
 17  \w   -119.00 -73.00   0.50    0.05    --  -75.71-126.00-120.00   92
 18  \w   -119.00 -73.00   0.50    0.05    --  -75.71-126.00 -30.00   92
 19  \w   -119.00 -73.00   0.50    0.05    --  -75.71-126.00  90.00   92
 20  \w   -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       '\w 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/[\s^2^(Fo^2^)+(0.0382P)^2^+6.0138P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            d6cc01072e2.cif
_cod_data_source_block           CH_borylated_BOB_anhydride
_cod_depositor_comments
'Adding full bibliography for 7135662--7135668.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7135663
_shelx_shelxl_version_number     2025/1
_shelx_estimated_absorpt_t_min   0.265
_shelx_estimated_absorpt_t_max   0.508
_shelx_res_checksum              37240