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_7135668
_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         'C23 H18 B N4, 0.5(C6 H6), Cl'
_chemical_formula_sum            'C26 H21 B Cl N4'
_chemical_formula_weight         435.73
_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             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                 95.110(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.169(3)
_cell_length_b                   17.046(2)
_cell_length_c                   13.646(2)
_cell_measurement_reflns_used    26328
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.5210
_cell_measurement_theta_min      3.4430
_cell_volume                     4441.2(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (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 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
 
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     19.00  65.00   0.50    5.21    --   59.71 -96.00 -92.00   92
  2  \w    -67.00 -21.00   0.50    5.21    --  -61.52  96.00  16.00   92
  3  \w    -77.00 -31.00   0.50    5.21    --  -71.46  96.00  16.00   92
  4  \w     33.00  79.00   0.50    5.21    --   73.27 -96.00 -92.00   92
  5  \w    -82.00 -36.00   0.50    5.21    --  -76.37  96.00  16.00   92
  6  \w     40.00  86.00   0.50    5.21    --   80.30 -96.00 -92.00   92
  7  \w    -91.00 -56.00   0.50    5.21    --  -42.00 -39.00  47.53   70
  8  \w     58.00  88.00   0.50    5.21    --   42.00  52.00-168.20   60
  9  \w    -92.00 -62.00   0.50    5.21    --  -46.00 -51.00 102.59   60
 10  \w    -92.00 -61.00   0.50    5.21    --  -46.00 -52.00-169.57   62
 11  \w    -96.00 -66.00   0.50    5.21    --  -50.00 -51.00-127.22   60
 12  \w   -105.00 -74.00   0.50    5.21    --  -58.00 -50.00  56.36   62
 13  \w   -104.00 -74.00   0.50    5.21    --  -58.00 -51.00 176.29   60
 14  \w   -105.00 -74.00   0.50    5.21    --  -58.00 -50.00 -73.28   62
 15  \w   -105.00 -74.00   0.50    5.21    --  -58.00 -50.00 138.62   62
 16  \w   -105.00 -74.00   0.50    5.21    --  -58.00 -49.00 -50.07   62
 17  \w     19.00  65.00   0.50    5.21    --   59.71 -95.00  90.00   92
 18  \w   -109.00 -78.00   0.50    5.21    --  -62.00 -47.00  84.38   62
 19  \w   -114.00 -85.00   0.50    5.21    --  -70.00 -59.00 129.44   58
 20  \w   -115.00 -85.00   0.50    5.21    --  -70.00 -55.00  -5.88   60
 21  \w    -56.00 -28.00   0.50    5.21    --  -70.00  67.00  -5.70   56
 22  \w     33.00  79.00   0.50    5.21    --   73.27 -95.00 120.00   92
 23  \w   -123.00 -88.00   0.50    5.21    --  -74.00 -39.00  46.57   70
 24  \w   -123.00 -88.00   0.50    5.21    --  -74.00 -40.00 -96.37   70
 25  \w   -124.00 -56.00   0.50    5.21    --  -76.37 -15.00 -30.00  136
 26  \w    -92.00 -33.00   0.50    5.21    --  -76.37 112.00 150.00  118
 27  \w    -92.00 -33.00   0.50    5.21    --  -76.37 112.00  90.00  118
 28  \w   -126.00 -96.00   0.50    5.21    --  -79.50 -49.00 -62.03   60
 29  \w    -97.00 -35.00   0.50    5.21    --  -79.50 116.00-146.98  124
 30  \w   -128.00 -94.00   0.50    5.21    --  -79.50 -40.00-134.47   68
 31  \w    -97.00 -36.00   0.50    5.21    --  -79.50 115.00 101.24  122
 32  \w    -97.00 -36.00   0.50    5.21    --  -79.50 114.00 121.70  122
 33  \w    -98.00 -35.00   0.50    5.21    --  -79.50 118.00  40.03  126
 34  \w    -97.00 -36.00   0.50    5.21    --  -79.50 115.00  54.44  122
 35  \w    -97.00 -36.00   0.50    5.21    --  -79.50 115.00 137.16  122
 36  \w   -126.00 -96.00   0.50    5.21    --  -79.50 -49.00 -14.28   60
 37  \w    -97.00 -36.00   0.50    5.21    --  -79.50 114.00-111.00  122
 38  \w    -97.00 -35.00   0.50    5.21    --  -79.50 116.00-127.49  124
 39  \w   -122.00 -95.00   0.50    5.21    --  -79.50 -65.00 -24.00   54
 40  \w    -97.00 -36.00   0.50    5.21    --  -79.50 115.00  83.01  122
 41  \w    -97.00 -36.00   0.50    5.21    --  -79.50 115.00 -40.68  122
 42  \w   -102.00 -34.00   0.50    5.21    --  -79.50 130.00  87.42  136
 43  \w    -97.00 -36.00   0.50    5.21    --  -79.50 114.00  15.06  122
 44  \w    -97.00 -36.00   0.50    5.21    --  -79.50 115.00-165.35  122
 45  \w   -128.00 -94.00   0.50    5.21    --  -79.50 -42.00 -33.38   68
 46  \w   -123.00 -93.00   0.50    5.21    --  -79.50 -62.00  21.13   60
 47  \w   -125.00 -95.00   0.50    5.21    --  -79.50 -54.00-103.71   60
 48  \w    -97.00 -36.00   0.50    5.21    --  -79.50 115.00 147.06  122
 49  \w     54.00 128.00   0.50    5.21    --   80.30  15.00   0.00  148
 50  \w     54.00 128.00   0.50    5.21    --   80.30  15.00   0.00  148
 51  \w     40.00  86.00   0.50    5.21    --   80.30 -95.00 120.00   92
 52  \w     54.00 128.00   0.50    5.21    --   80.30  15.00 150.00  148
 53  \w     54.00 128.00   0.50    5.21    --   80.30  15.00-120.00  148
 54  \w     54.00 128.00   0.50    5.21    --   80.30  15.00 -60.00  148
 55  \w     54.00 128.00   0.50    5.21    --   80.30  15.00 -60.00  148
 56  \w     42.00  91.00   0.50    5.21    --   83.50 -99.00-142.02   98
 57  \w     42.00  93.00   0.50    5.21    --   83.50-101.00  37.28  102
 58  \w     42.00  93.00   0.50    5.21    --   83.50-101.00 -26.89  102
 59  \w    -32.00  -6.00   0.50    5.21    --  -14.00 114.00-162.31   52
 60  \w     28.00  56.00   0.50    5.21    --   14.00  60.00-103.40   56
 61  \w    -49.00 -21.00   0.50    5.21    --  -18.00 136.00 -64.91   56
 62  \w     32.00  60.00   0.50    5.21    --   18.00  58.00  13.12   56
 63  \w     32.00  60.00   0.50    5.21    --   18.00  59.00 -54.72   56
 64  \w     32.00  60.00   0.50    5.21    --   18.00  58.00 177.72   56
 65  \w     54.00  84.00   0.50    5.21    --   38.00  52.00  33.61   60
;
_diffrn_measurement_device       'four-circle diffractometer'
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;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0594389000
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_diffrn_orient_matrix_UB_31      -0.0284214000
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.310
_diffrn_reflns_theta_min         3.476
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    1.680
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_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.30a (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            'intense orange'
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_exptl_crystal_description       plate
_exptl_crystal_F_000             1816
_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          0.210
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0897P)^2^+8.0424P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01072e2.cif
_cod_data_source_block           '[1bpy]Cl'
_cod_depositor_comments
'Adding full bibliography for 7135662--7135668.cif.'
_cod_original_cell_volume        4440.9(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7135668
_shelx_shelxl_version_number     2025/1
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_shelx_res_checksum              8364