Alkali metal salts of 1,2,3-benzodiazaborines: platforms for late-stage N-functionalization and metal complexation
Wüst, Leonie; Scheuring, Lea; Wellnitz, Tim; Radacki, Krzysztof; Braunschweig, Holger; Chemical Science 16 (2025) 9934–9942; doi:10.1039/D5SC01395J

data_1574512
_publ_section_title
;
 Alkali metal salts of 1,2,3-benzodiazaborines: platforms for late-stage
 N-functionalization and metal complexation
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              9934
_journal_page_last               9942
_journal_paper_doi               10.1039/D5SC01395J
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C17 H19 B N2'
_chemical_formula_sum            'C17 H19 B N2'
_chemical_formula_weight         262.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-11-07
_audit_creation_method           'CIF-fill 1.4o (K.Radacki, 2005-23)'
_audit_update_record
;
2025-02-20 deposited with the CCDC.	2025-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                119.224(2)
_cell_angle_beta                 97.4680(10)
_cell_angle_gamma                92.8740(10)
_cell_formula_units_Z            6
_cell_length_a                   12.25790(10)
_cell_length_b                   14.7917(2)
_cell_length_c                   14.9932(3)
_cell_measurement_reflns_used    22770
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.1180
_cell_measurement_theta_min      3.4030
_cell_volume                     2332.00(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.89a (Rigaku OD, 2023)'
_computing_data_collection
;
 CrysAlisPro system (CCD 43.76a 64-bit (release 21-06-2023))
;
_computing_data_reduction        'CrysAlisPro 1.171.43.89a (Rigaku OD, 2023)'
_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 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 0.993
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -91.00 -56.00   0.50    0.82    --  -42.00 -48.00 109.82   70
  2  \w   -102.00 -67.00   0.50    0.82    --  -54.00 -51.00 -94.51   70
  3  \w   -102.00 -67.00   0.50    0.82    --  -54.00 -52.00 160.50   70
  4  \w   -104.00 -67.00   0.50    0.82    --  -54.00 -44.00 -55.78   74
  5  \w   -103.00 -68.00   0.50    0.82    --  -54.00 -50.00  25.91   70
  6  \w   -107.00 -72.00   0.50    0.82    --  -58.00 -50.00-160.23   70
  7  \w     20.00  86.00   0.50    0.82    --   58.45-126.00 -30.00  132
  8  \w   -111.00 -76.00   0.50    0.82    --  -62.00 -48.00-125.52   70
  9  \w   -115.00 -80.00   0.50    0.82    --  -66.00 -48.00  72.81   70
 10  \w   -119.00 -84.00   0.50    0.82    --  -70.00 -47.00 136.21   70
 11  \w   -120.00 -86.00   0.50    0.82    --  -74.00 -59.00  17.09   68
 12  \w   -124.00 -86.00   0.50    0.82    --  -74.00 -43.00  97.84   76
 13  \w   -124.00 -87.00   0.50    0.82    --  -74.00 -44.00 -18.00   74
 14  \w    -92.00 -31.00   0.50    0.82    --  -76.37 112.00 -90.00  122
 15  \w    -97.00 -32.00   0.50    0.82    --  -78.00 114.00 -52.04  130
 16  \w    -97.00 -32.00   0.50    0.82    --  -78.00 114.00-168.28  130
 17  \w    -97.00 -32.00   0.50    0.82    --  -78.00 114.00  47.30  130
 18  \w    -97.00 -33.00   0.50    0.82    --  -79.50 115.00-139.74  128
 19  \w   -128.00 -93.00   0.50    0.82    --  -79.50 -50.00 162.12   70
 20  \w   -126.00 -93.00   0.50    0.82    --  -79.50-120.00-161.22   66
 21  \w   -126.00 -92.00   0.50    0.82    --  -79.50-123.00 -29.36   68
 22  \w   -126.00 -93.00   0.50    0.82    --  -79.50-121.00 177.05   66
 23  \w    -97.00 -33.00   0.50    0.82    --  -79.50 115.00 -32.82  128
 24  \w   -126.00 -93.00   0.50    0.82    --  -79.50-121.00-118.69   66
 25  \w    -97.00 -33.00   0.50    0.82    --  -79.50 116.00  96.57  128
 26  \w   -126.00 -93.00   0.50    0.82    --  -79.50-121.00 168.22   66
 27  \w   -130.00 -91.00   0.50    0.82    --  -79.50 -41.00  37.60   78
 28  \w   -128.00 -93.00   0.50    0.82    --  -79.50 -50.00-164.30   70
 29  \w   -125.00 -91.00   0.50    0.82    --  -79.50 -60.00 125.92   68
 30  \w   -130.00 -91.00   0.50    0.82    --  -79.50 -40.00 -99.13   78
 31  \w   -129.00 -93.00   0.50    0.82    --  -79.50 -47.00-175.75   72
 32  \w   -127.00 -92.00   0.50    0.82    --  -79.50 -53.00-128.34   70
 33  \w   -126.00 -92.00   0.50    0.82    --  -79.50-123.00 -57.92   68
 34  \w   -126.00 -93.00   0.50    0.82    --  -79.50-120.00  43.51   66
 35  \w   -130.00 -92.00   0.50    0.82    --  -79.50 -42.00  15.56   76
 36  \w   -126.00 -93.00   0.50    0.82    --  -79.50-121.00 -96.39   66
 37  \w     40.00  90.00   0.50    0.82    --   82.26 -95.00 -60.00  100
 38  \w     40.00  90.00   0.50    0.82    --   82.26 -95.00-150.00  100
 39  \w     40.00  90.00   0.50    0.82    --   82.26 -95.00 -30.00  100
 40  \w     37.00  93.00   0.50    0.82    --   82.26-112.00   0.00  112
 41  \w     40.00  90.00   0.50    0.82    --   82.26 -95.00  30.00  100
 42  \w     40.00  90.00   0.50    0.82    --   82.26 -95.00-180.00  100
 43  \w     40.00  90.00   0.50    0.82    --   82.26 -95.00 120.00  100
 44  \w     37.00  93.00   0.50    0.82    --   82.26-112.00  30.00  112
 45  \w     43.00  92.00   0.50    0.82    --   85.25 -96.00  81.80   98
 46  \w     42.00  93.00   0.50    0.82    --   85.25 -98.00 168.65  102
 47  \w     42.00  93.00   0.50    0.82    --   85.25 -97.00  55.71  102
 48  \w     21.00  49.00   0.50    0.82    --   10.00  62.00-165.58   56
 49  \w    -54.00 -27.00   0.50    0.82    --  -14.00 -54.00 -64.60   54
 50  \w    -40.00  -8.00   0.50    0.82    --  -18.00 118.00-168.37   64
 51  \w    -70.00 -35.00   0.50    0.82    --  -22.00 -51.00  25.68   70
 52  \w     34.00  60.00   0.50    0.82    --   22.00  59.00-136.49   52
 53  \w     34.00  60.00   0.50    0.82    --   22.00  59.00 -89.23   52
 54  \w     34.00  60.00   0.50    0.82    --   22.00  58.00  26.37   52
 55  \w   -119.00 -84.00   0.50    0.82    --  -70.00 -48.00 -61.65   70
 56  \w   -121.00 -86.00   0.50    0.82    --  -74.00 -57.00 -88.39   70
 57  \w   -121.00 -86.00   0.50    0.82    --  -74.00 -58.00 -65.84   70
 58  \w   -121.00 -86.00   0.50    0.82    --  -74.00 -56.00  68.74   70
 59  \w   -121.00 -86.00   0.50    0.82    --  -74.00 -57.00 132.37   70
 60  \w   -121.00 -86.00   0.50    0.82    --  -74.00 -57.00-120.16   70
 61  \w   -127.00 -40.00   0.50    0.82    --  -76.37 -15.00  30.00  174
 62  \w    -92.00 -31.00   0.50    0.82    --  -76.37 112.00 150.00  122
 63  \w   -124.00 -89.00   0.50    0.82    --  -78.00 -61.00 -22.18   70
 64  \w   -126.00 -92.00   0.50    0.82    --  -79.50-123.00  76.52   68
 65  \w   -126.00 -93.00   0.50    0.82    --  -79.50-121.00 135.81   66
 66  \w   -126.00 -93.00   0.50    0.82    --  -79.50-120.00  25.28   66
 67  \w    -97.00 -33.00   0.50    0.82    --  -79.50 115.00  15.51  128
 68  \w   -126.00 -93.00   0.50    0.82    --  -79.50-121.00   2.13   66
;
_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      -0.0487188000
_diffrn_orient_matrix_UB_12      0.0219039000
_diffrn_orient_matrix_UB_13      -0.0865331000
_diffrn_orient_matrix_UB_21      -0.0855106000
_diffrn_orient_matrix_UB_22      0.0608266000
_diffrn_orient_matrix_UB_23      0.0655656000
_diffrn_orient_matrix_UB_31      0.0816265000
_diffrn_orient_matrix_UB_32      0.1015493000
_diffrn_orient_matrix_UB_33      0.0502444000
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            53716
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.182
_diffrn_reflns_theta_min         3.432
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.43.89a (Rigaku Oxford Diffraction, 2023) 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    1.120
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_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          0.340
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         9136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1148P)^2^+1.3730P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1838
_refine_ls_wR_factor_ref         0.1973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7516
_reflns_number_total             9136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           6-H
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_original_cell_volume        2331.99(7)
_cod_database_code               1574512
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.849
_shelx_estimated_absorpt_t_max   0.976
_spezial-alerts:
;
 PLAT097:
 
 _vrf_PLAT097_2_B
 
 PROBLEM: Large Reported Max. (Positive) Residual Density 0.83 from C4_6
 RESPONSE: Due to the synthesis of durylbromide is a twofold bromination as side product possible.
 Small amounts of entrained dibromoduryl impurities lead to residual density at the para carbon atom.
;
_shelx_res_checksum              38910
_shelx_hkl_checksum              70678