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_1574515
_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         'C76 H88 B4 Br2 Mg4 N8 O3, 2(C5 H12)'
_chemical_formula_sum            'C86 H112 B4 Br2 Mg4 N8 O3'
_chemical_formula_weight         1606.13
_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             2023-12-06
_audit_creation_method           'CIF-fill 1.4p (K.Radacki, 2005-23)'
_audit_update_record
;
2025-02-20 deposited with the CCDC.	2025-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                70.547(2)
_cell_angle_beta                 74.162(2)
_cell_angle_gamma                76.507(2)
_cell_formula_units_Z            2
_cell_length_a                   15.0166(2)
_cell_length_b                   16.5087(3)
_cell_length_c                   19.7579(4)
_cell_measurement_reflns_used    32497
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6690
_cell_measurement_theta_min      2.8620
_cell_volume                     4388.02(15)
_computing_cell_refinement       'CrysAlisPro 1.171.43.89a (Rigaku OD, 2023)'
_computing_data_collection
;
 CrysAlisPro system (CCD 42.102a 64-bit (release 15-09-2023))
;
_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 0.992
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     35.00  99.00   0.50    0.38    --   82.26-122.00 -93.00  128
  2  \w     24.00  96.00   0.50    0.38    --   71.26-122.00 -93.00  144
  3  \w     17.00  83.00   0.50    0.38    --   58.45-122.00 -93.00  132
  4  \w     42.00  93.00   0.50    0.38    --   85.25 -98.00-175.14  102
  5  \w     42.00  93.00   0.50    0.38    --   85.25 -97.00-102.26  102
  6  \w     43.00  92.00   0.50    0.38    --   85.25 -96.00 -53.99   98
  7  \w     43.00  92.00   0.50    0.38    --   85.25 -96.00  -0.96   98
  8  \w     40.00  90.00   0.50    0.38    --   82.26 -95.00  30.00  100
  9  \w     40.00  90.00   0.50    0.38    --   82.26 -95.00  60.00  100
 10  \w     43.00  92.00   0.50    0.38    --   85.25 -95.00  88.74   98
 11  \w     40.00  90.00   0.50    0.38    --   82.26 -95.00 150.00  100
 12  \w     40.00  90.00   0.50    0.38    --   82.26 -95.00 120.00  100
 13  \w     43.00  92.00   0.50    0.38    --   85.25 -94.00 -44.37   98
 14  \w     46.00 133.00   0.50    0.38    --   82.26  15.00 -60.00  174
 15  \w     96.00 133.00   0.50    0.38    --   85.25 126.00-115.09   74
 16  \w     59.00  94.00   0.50    0.38    --   46.00  52.00 -50.05   70
 17  \w     30.00  56.00   0.50    0.38    --   18.00  60.00-141.92   52
 18  \w     34.00  60.00   0.50    0.38    --   22.00  59.00-104.37   52
 19  \w     25.00  54.00   0.50    0.38    --   14.00  61.00 -44.38   58
 20  \w     25.00  54.00   0.50    0.38    --   14.00  61.00  62.67   58
 21  \w     16.00  43.00   0.50    0.38    --    6.00  65.00 178.03   54
 22  \w   -107.00 -33.00   0.50    0.38    --  -79.50 137.00   9.15  148
 23  \w    -99.00 -29.00   0.50    0.38    --  -76.37 122.00 -12.00  140
 24  \w    -94.00 -22.00   0.50    0.38    --  -69.54 122.00 -12.00  144
 25  \w    -85.00 -13.00   0.50    0.38    --  -60.16 122.00 -12.00  144
 26  \w    -97.00 -32.00   0.50    0.38    --  -78.00 115.00 -73.16  130
 27  \w    -97.00 -32.00   0.50    0.38    --  -78.00 114.00-117.95  130
 28  \w    -92.00 -31.00   0.50    0.38    --  -76.37 112.00  60.00  122
 29  \w    -97.00 -32.00   0.50    0.38    --  -78.00 114.00 173.01  130
 30  \w    -92.00 -34.00   0.50    0.38    --  -79.50 107.00 149.26  116
 31  \w    -70.00 -35.00   0.50    0.38    --  -22.00 -52.00  90.75   70
 32  \w    -87.00 -52.00   0.50    0.38    --  -38.00 -50.00  67.22   70
 33  \w    -87.00 -52.00   0.50    0.38    --  -38.00 -48.00  -2.68   70
 34  \w   -125.00 -91.00   0.50    0.38    --  -79.50 -60.00  78.32   68
 35  \w   -125.00 -91.00   0.50    0.38    --  -79.50 -60.00  84.84   68
 36  \w   -117.00 -84.00   0.50    0.38    --  -70.00 -57.00 132.95   66
 37  \w   -123.00 -97.00   0.50    0.38    --  -79.50 -66.00 147.08   52
 38  \w   -117.00 -83.00   0.50    0.38    --  -70.00 -55.00  79.93   68
 39  \w   -117.00 -83.00   0.50    0.38    --  -70.00 -55.00  24.39   68
 40  \w   -125.00 -90.00   0.50    0.38    --  -78.00 -55.00 103.30   70
 41  \w   -124.00 -95.00   0.50    0.38    --  -79.50 -65.00 -81.00   58
 42  \w   -118.00 -83.00   0.50    0.38    --  -70.00 -54.00 -46.00   70
 43  \w   -127.00 -92.00   0.50    0.38    --  -79.50 -53.00 -11.63   70
 44  \w   -106.00 -71.00   0.50    0.38    --  -58.00 -51.00 -17.65   70
 45  \w   -128.00 -93.00   0.50    0.38    --  -79.50 -51.00  -4.20   70
 46  \w   -127.00 -92.00   0.50    0.38    --  -79.50 -54.00 -67.76   70
 47  \w   -120.00 -86.00   0.50    0.38    --  -74.00 -60.00-172.20   68
 48  \w   -120.00 -86.00   0.50    0.38    --  -74.00 -59.00-146.16   68
 49  \w   -128.00 -93.00   0.50    0.38    --  -79.50 -49.00-110.37   70
 50  \w   -107.00 -72.00   0.50    0.38    --  -58.00 -49.00-103.84   70
 51  \w   -120.00 -83.00   0.50    0.38    --  -70.00 -46.00 103.48   74
 52  \w   -103.00 -68.00   0.50    0.38    --  -54.00 -50.00 140.43   70
 53  \w   -116.00 -79.00   0.50    0.38    --  -66.00 -45.00 174.95   74
 54  \w   -130.00 -91.00   0.50    0.38    --  -79.50 -39.00  38.73   78
 55  \w   -130.00 -91.00   0.50    0.38    --  -79.50 -41.00 161.64   78
 56  \w   -128.00 -93.00   0.50    0.38    --  -79.50 -50.00 156.26   70
 57  \w   -129.00 -92.00   0.50    0.38    --  -79.50 -44.00 -33.96   74
 58  \w   -120.00 -83.00   0.50    0.38    --  -70.00 -44.00-145.46   74
 59  \w   -126.00 -93.00   0.50    0.38    --  -79.50-120.00-164.89   66
 60  \w   -126.00 -84.00   0.50    0.38    --  -79.50-138.00-170.32   84
 61  \w   -126.00 -88.00   0.50    0.38    --  -79.50-130.00-105.71   76
 62  \w   -127.00 -89.00   0.50    0.38    --  -79.50-129.00 -20.04   76
 63  \w   -126.00 -93.00   0.50    0.38    --  -79.50-121.00   9.89   66
 64  \w   -126.00 -92.00   0.50    0.38    --  -79.50-123.00  50.23   68
 65  \w   -126.00 -92.00   0.50    0.38    --  -79.50-123.00  77.09   68
 66  \w   -126.00 -92.00   0.50    0.38    --  -79.50-123.00 144.64   68
;
_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      -0.0115801000
_diffrn_orient_matrix_UB_12      -0.0481586000
_diffrn_orient_matrix_UB_13      -0.0510362000
_diffrn_orient_matrix_UB_21      -0.0241818000
_diffrn_orient_matrix_UB_22      -0.0784010000
_diffrn_orient_matrix_UB_23      0.0669405000
_diffrn_orient_matrix_UB_31      -0.1045969000
_diffrn_orient_matrix_UB_32      0.0397016000
_diffrn_orient_matrix_UB_33      0.0087764000
_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  0.0525
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            100626
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.275
_diffrn_reflns_theta_min         2.874
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.457
_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    1.216
_exptl_crystal_description       plate
_exptl_crystal_F_000             1692
_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          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.650
_refine_diff_density_min         -1.060
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     978
_refine_ls_number_reflns         17296
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0787
_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^)+(0.1258P)^2^+8.6922P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2220
_refine_ls_wR_factor_ref         0.2354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13403
_reflns_number_total             17296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_database_code               1574515
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.667
_shelx_estimated_absorpt_t_max   0.898
_shelx_res_checksum              36445
_shelx_hkl_checksum              84008