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_7135667
_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 H10 B Cl N2'
_chemical_formula_sum            'C13 H10 B Cl N2'
_chemical_formula_weight         240.49
_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             2024-09-20
_audit_creation_method           'CIF-fill 1.5e (K.Radacki, 2005-23)'
_audit_update_record
;
2026-02-15 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.60800(10)
_cell_length_b                   6.84400(10)
_cell_length_c                   17.5242(2)
_cell_measurement_reflns_used    20283
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.2220
_cell_measurement_theta_min      4.6070
_cell_volume                     1147.68(2)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
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  1  \w     39.00 105.00   0.50    0.12    --   80.50-135.00-159.66  132
  2  \w     36.00  97.00   0.50    0.12    --   76.61-125.00 -60.00  122
  3  \w     33.00  94.00   0.50    0.12    --   73.60-125.00 -30.00  122
  4  \w     35.00  82.00   0.50    0.12    --   73.60-106.00 -65.00   94
  5  \w     38.00  85.00   0.50    0.12    --   76.61-106.00 -65.00   94
  6  \w     22.00  68.00   0.50    0.12    --   60.09-106.00 -65.00   92
  7  \w     39.00  99.00   0.50    0.12    --   80.50-121.00 -11.55  120
  8  \w     40.00  96.00   0.50    0.12    --   80.50-116.00  17.96  112
  9  \w     53.00 121.00   0.50    0.12    --   76.61  15.00 150.00  136
 10  \w     53.00 121.00   0.50    0.12    --   76.61  15.00 150.00  136
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 16  \w    -83.00 -55.00   0.50    0.12    --  -38.00 -40.00 -94.83   56
 17  \w    -79.00 -52.00   0.50    0.12    --  -34.00 -42.00 -11.95   54
 18  \w    -76.00 -47.00   0.50    0.12    --  -30.00 -39.00  33.77   58
 19  \w    -67.00 -40.00   0.50    0.12    --  -22.00 -43.00  76.19   54
 20  \w    -83.00 -56.00   0.50    0.12    --  -38.00 -42.00 148.88   54
 21  \w    -88.00 -59.00   0.50    0.12    --  -42.00 -39.00 113.23   58
 22  \w   -123.00 -97.00   0.50    0.12    --  -78.50 -45.00  21.55   52
 23  \w   -123.00 -97.00   0.50    0.12    --  -78.50 -44.00  67.20   52
 24  \w   -107.00 -80.00   0.50    0.12    --  -62.00 -44.00 102.48   54
 25  \w   -123.00 -97.00   0.50    0.12    --  -78.50 -43.00  36.64   52
 26  \w   -123.00 -97.00   0.50    0.12    --  -78.50 -45.00 -25.21   52
 27  \w   -119.00 -92.00   0.50    0.12    --  -74.00 -43.00 -14.44   54
 28  \w   -123.00 -97.00   0.50    0.12    --  -78.50 -43.00 102.94   52
 29  \w   -124.00 -96.00   0.50    0.12    --  -78.50 -42.00 157.81   56
 30  \w   -124.00 -96.00   0.50    0.12    --  -78.50 -42.00 125.76   56
 31  \w   -119.00 -92.00   0.50    0.12    --  -74.00 -41.00  83.57   54
 32  \w   -115.00 -88.00   0.50    0.12    --  -70.00 -43.00 -53.47   54
 33  \w    -99.00 -72.00   0.50    0.12    --  -54.00 -44.00-108.22   54
 34  \w   -123.00 -97.00   0.50    0.12    --  -78.50 -45.00-155.56   52
 35  \w   -124.00 -96.00   0.50    0.12    --  -78.50 -39.00-129.98   56
 36  \w   -109.00 -78.00   0.50    0.12    --  -62.00 -34.00  -6.99   62
 37  \w   -116.00 -86.00   0.50    0.12    --  -70.00 -33.00-163.95   60
 38  \w   -100.00 -71.00   0.50    0.12    --  -54.00 -34.00  20.60   58
 39  \w   -125.00 -94.00   0.50    0.12    --  -78.50 -30.00 -67.41   62
 40  \w   -126.00 -93.00   0.50    0.12    --  -78.50 -28.00 -92.88   66
 41  \w   -120.00 -58.00   0.50    0.12    --  -75.12 -15.00-150.00  124
 42  \w   -124.00 -80.00   0.50    0.12    --  -78.50 -20.00   4.94   88
 43  \w   -120.00 -58.00   0.50    0.12    --  -75.12 -15.00 -60.00  124
 44  \w   -124.00 -96.00   0.50    0.12    --  -78.50 -39.00 107.82   56
 45  \w   -124.00 -96.00   0.50    0.12    --  -78.50 -39.00 142.99   56
 46  \w   -104.00 -74.00   0.50    0.12    --  -58.00 -33.00 156.18   60
 47  \w   -120.00 -58.00   0.50    0.12    --  -75.12 -15.00 150.00  124
 48  \w    -85.00 -39.00   0.50    0.12    --  -78.50 103.00  95.83   92
 49  \w   -101.00 -37.00   0.50    0.12    --  -78.50 128.00 142.27  128
 50  \w   -103.00 -37.00   0.50    0.12    --  -78.50 131.00 108.04  132
 51  \w   -100.00 -37.00   0.50    0.12    --  -78.50 127.00 170.55  126
 52  \w   -102.00 -37.00   0.50    0.12    --  -78.50 129.00  19.43  130
 53  \w   -100.00 -36.00   0.50    0.12    --  -78.50 126.00  27.44  128
 54  \w   -100.00 -36.00   0.50    0.12    --  -78.50 126.00  58.06  128
 55  \w    -98.00 -37.00   0.50    0.12    --  -78.50 123.00  82.76  122
 56  \w    -95.00 -34.00   0.50    0.12    --  -75.12 125.00 150.00  122
 57  \w    -70.00 -23.00   0.50    0.12    --  -61.72 106.00  33.00   94
 58  \w   -103.00 -37.00   0.50    0.12    --  -78.50 131.00  -9.07  132
 59  \w    -83.00 -36.00   0.50    0.12    --  -75.12 106.00  33.00   94
 60  \w    -80.00 -33.00   0.50    0.12    --  -71.97 106.00  33.00   94
 61  \w    -95.00 -34.00   0.50    0.12    --  -75.12 125.00 -30.00  122
 62  \w    -96.00 -37.00   0.50    0.12    --  -78.50 120.00 -67.41  118
 63  \w   -103.00 -37.00   0.50    0.12    --  -78.50 131.00-129.49  132
 64  \w    -77.00 -20.00   0.50    0.12    --  -50.00 135.00 -93.61  114
 65  \w    -32.00  -6.00   0.50    0.12    --  -18.00 114.00-167.18   52
 66  \w     17.00  43.00   0.50    0.12    --   -2.00  46.00  97.42   52
;
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_diffrn_orient_matrix_type
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0720794000
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_diffrn_orient_matrix_UB_21      0.1149222000
_diffrn_orient_matrix_UB_22      -0.1390461000
_diffrn_orient_matrix_UB_23      -0.0233552000
_diffrn_orient_matrix_UB_31      0.0866070000
_diffrn_orient_matrix_UB_32      0.1768406000
_diffrn_orient_matrix_UB_33      -0.0226438000
_diffrn_radiation_monochromator  'multi-layer mirror'
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0092
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_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25802
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.915
_diffrn_reflns_theta_min         4.621
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
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_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.424
_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            'clear colourless'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_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          0.320
_exptl_crystal_size_mid          0.200
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.3081P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
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_reflns_number_total             2287
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01072e2.cif
_cod_data_source_block           1Cl
_cod_depositor_comments
'Adding full bibliography for 7135662--7135668.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7135667
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.477
_shelx_estimated_absorpt_t_max   0.876
_shelx_res_checksum              70402