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_7135662
_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         'C13 H11 B Br N2, Br'
_chemical_formula_sum            'C13 H11 B Br2 N2'
_chemical_formula_weight         365.87
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2026-02-04
_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                 101.367(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.835(8)
_cell_length_b                   6.108(5)
_cell_length_c                   22.159(3)
_cell_measurement_reflns_used    5216
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.9150
_cell_measurement_theta_min      4.0550
_cell_volume                     1437.7(16)
_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 2014/5 (Sheldrick, 2014)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details
;
 
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     14.00  80.00   0.50    0.20    --   58.60-116.00-131.00  132
  2  \w     25.00  92.00   0.50    0.20    --   71.26-116.00-131.00  134
  3  \w     31.00  98.00   0.50    0.80    --   76.61-116.00-131.00  134
  4  \w     38.00  97.00   0.50    0.80    --   84.39-116.00-131.00  118
  5  \w     64.00  90.00   0.50    0.80    --   84.39 -95.00 -90.00   52
  6  \w     34.00  84.00   0.50    0.80    --   76.61 -95.00 -90.00  100
  7  \w     34.00  84.00   0.50    0.80    --   76.61 -95.00 -60.00  100
  8  \w     43.00  92.00   0.50    0.80    --   84.39 -95.00-120.00   98
  9  \w     66.00  92.00   0.50    0.80    --   84.39 -95.00 -60.00   52
 10  \w     62.00  92.00   0.50    0.80    --   84.39 -95.00 -30.00   60
 11  \w     56.00  92.00   0.50    0.80    --   84.39 -95.00  90.00   72
 12  \w     16.00  66.00   0.50    0.20    --   58.60 -95.00 120.00  100
 13  \w   -124.00 -86.00   0.50    0.80    --  -74.00 -43.00 119.71   76
 14  \w   -124.00 -98.00   0.50    0.80    --  -79.50 -63.00 160.82   52
 15  \w   -124.00 -95.00   0.50    0.80    --  -79.50 -65.00  45.48   58
 16  \w   -122.00 -87.00   0.50    0.80    --  -74.00 -53.00  61.14   70
 17  \w   -127.00 -95.00   0.50    0.80    --  -79.50 -53.00  15.41   64
 18  \w   -119.00 -84.00   0.50    0.20    --  -70.00 -47.00 -47.71   70
 19  \w   -106.00 -71.00   0.50    0.20    --  -58.00 -52.00 -62.67   70
 20  \w   -126.00 -93.00   0.50    0.80    --  -79.50 -47.00-130.18   66
 21  \w   -122.00 -87.00   0.50    0.80    --  -74.00 -52.00-148.22   70
 22  \w   -121.00 -86.00   0.50    0.80    --  -74.00 -57.00 -95.51   70
 23  \w   -124.00 -87.00   0.50    0.80    --  -74.00 -45.00 -84.86   74
 24  \w   -120.00 -83.00   0.50    0.20    --  -70.00 -46.00 173.82   74
 25  \w   -128.00 -98.00   0.50    0.80    --  -79.50 -47.00 171.65   60
 26  \w   -125.00-100.00   0.50    0.80    --  -79.50-113.00 -54.63   50
 27  \w    -91.00 -24.00   0.50    0.20    --  -69.94 116.00 -43.00  134
 28  \w    -97.00 -30.00   0.50    0.80    --  -76.30 116.00 -43.00  134
 29  \w    -81.00 -14.00   0.50    0.20    --  -60.30 116.00 -43.00  134
;
_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      0.0433196000
_diffrn_orient_matrix_UB_12      -0.0130210000
_diffrn_orient_matrix_UB_13      -0.0620594000
_diffrn_orient_matrix_UB_21      -0.0198168000
_diffrn_orient_matrix_UB_22      0.2487095000
_diffrn_orient_matrix_UB_23      -0.0086373000
_diffrn_orient_matrix_UB_31      0.1369631000
_diffrn_orient_matrix_UB_32      0.0399885000
_diffrn_orient_matrix_UB_33      0.0332374000
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13947
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.794
_diffrn_reflns_theta_min         4.070
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    7.001
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.885
_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 pale colourless'
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_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          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0630P)^2^+2.0656P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2257
_reflns_number_total             2796
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01072e2.cif
_cod_data_source_block           '[1Br]HBr'
_cod_depositor_comments
'Adding full bibliography for 7135662--7135668.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7135662
_shelx_shelxl_version_number     2025/1
_shelx_estimated_absorpt_t_min   0.487
_shelx_estimated_absorpt_t_max   0.604
_shelx_res_checksum              63968