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_7135665
_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         '2(C13 H9 B2 Br3 N2), C H2 Cl2'
_chemical_formula_sum            'C27 H20 B4 Br6 Cl2 N4'
_chemical_formula_weight         994.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-05-06
_audit_creation_method           'CIF-fill 1.6f (K.Radacki, 2005-25)'
_audit_update_record
;
2026-02-15 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.423(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.1025(5)
_cell_length_b                   7.0534(2)
_cell_length_c                   35.7650(10)
_cell_measurement_reflns_used    4983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.9900
_cell_measurement_theta_min      3.4930
_cell_volume                     6332.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.44.108a (Rigaku OD, 2025)'
_computing_data_collection
;
 CrysAlisPro system (CCD 42.58a 64-bit (release 31-05-2022))
;
_computing_data_reduction        'CrysAlisPro 1.171.44.108a (Rigaku OD, 2025)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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 0.908
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details
;
 
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     64.00  91.00   0.50    0.39    --   65.37-126.00-180.00   54
  2  \w     29.00  72.00   0.50    0.39    --   65.37 -95.00   0.00   86
  3  \w     67.00  92.00   0.50    1.54    --   76.87-110.00  53.00   50
  4  \w     29.00  91.00   0.50    0.39    --   71.48-110.00  53.00  124
  5  \w     23.00  85.00   0.50    0.39    --   65.37-110.00  53.00  124
  6  \w     31.00  72.00   0.50    0.39    --   65.37 -95.00 -30.00   82
  7  \w     28.00  67.00   0.50    0.39    --   65.37 -95.00-120.00   78
  8  \w     54.00  80.00   0.50    1.54    --   76.87  15.00 150.00   52
  9  \w     84.00 109.00   0.50    1.54    --   76.87  15.00 150.00   50
 10  \w    -86.00 -61.00   0.50    0.39    --  -73.64 110.00 148.00   50
 11  \w    -85.00 -23.00   0.50    0.39    --  -65.03 110.00 148.00  124
 12  \w    -95.00 -33.00   0.50    1.54    --  -75.71 110.00 148.00  124
 13  \w   -117.00 -82.00   0.50    1.54    --  -75.71-126.00  30.00   70
 14  \w   -112.00 -86.00   0.50    1.54    --  -75.71-126.00 -30.00   52
 15  \w   -108.00 -77.00   0.50    1.54    --  -75.71-126.00 -90.00   62
 16  \w   -118.00 -73.00   0.50    1.54    --  -75.71-126.00-180.00   90
;
_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      -0.0353817000
_diffrn_orient_matrix_UB_12      0.0416569000
_diffrn_orient_matrix_UB_13      0.0340882000
_diffrn_orient_matrix_UB_21      0.0046968000
_diffrn_orient_matrix_UB_22      -0.2087210000
_diffrn_orient_matrix_UB_23      0.0122413000
_diffrn_orient_matrix_UB_31      0.0498932000
_diffrn_orient_matrix_UB_32      0.0490366000
_diffrn_orient_matrix_UB_33      0.0233509000
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            17945
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.751
_diffrn_reflns_theta_min         3.522
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    10.938
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.44.108a (Rigaku Oxford Diffraction, 2025) 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            colourless
_exptl_crystal_density_diffrn    2.085
_exptl_crystal_description       plate
_exptl_crystal_F_000             3792
_exptl_crystal_preparation
;
 Crystals were grown at RT from saturated solution in DCM. 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          0.102
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.007
_refine_diff_density_max         2.867
_refine_diff_density_min         -1.411
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0638
_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^)+(0.0985P)^2^+131.0719P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.1883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4450
_reflns_number_total             5489
_reflns_threshold_expression     'I > 2\s(I)'
_twin_dimensionality             triperiodic
_twin_formation_mechanism        gt
_twin_morphology                 polysynthetic
_twin_special_details
;
 Twin-law was computed with TwinRotMat as implemented in Platon.
 Component 2 rotated by 0.42\% around ( 0 0 1 ) (reciprocal)
 or [ 0 0 1 ] (direct) axis.
;
_cod_data_source_file            d6cc01072e2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7135662--7135668.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7135665
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.402
_shelx_estimated_absorpt_t_max   0.927
_shelx_res_checksum              49100