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_1574511
_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         'C52 H43 B6 K4 N17 O2'
_chemical_formula_sum            'C52 H43 B6 K4 N17 O2'
_chemical_formula_weight         1159.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-12-03
_audit_creation_method           'CIF-fill 1.5m (K.Radacki, 2005-24)'
_audit_update_record
;
2025-02-20 deposited with the CCDC.	2025-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.6090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2068(2)
_cell_length_b                   15.3061(2)
_cell_length_c                   14.4664(2)
_cell_measurement_reflns_used    36337
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.4190
_cell_measurement_theta_min      2.8520
_cell_volume                     2802.30(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection
;
 CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))
;
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_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 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 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     30.00  56.00   0.50    0.08    --   18.00  60.00  20.57   52
  2  \w     60.00  95.00   0.50    0.08    --   46.00  50.00  29.56   70
  3  \w     64.00  99.00   0.50    0.08    --   50.00  51.00  -0.94   70
  4  \w     52.00  87.00   0.50    0.08    --   38.00  51.00 -96.24   70
  5  \w     46.00 133.00   0.50    0.08    --   82.29  15.00-120.00  174
  6  \w     40.00  90.00   0.50    0.08    --   82.29 -95.00 -90.00  100
  7  \w     40.00  90.00   0.50    0.08    --   82.29 -95.00-150.00  100
  8  \w     40.00  90.00   0.50    0.08    --   82.29 -95.00-120.00  100
  9  \w     42.00  93.00   0.50    0.08    --   85.25 -98.00-172.01  102
 10  \w     41.00  93.00   0.50    0.08    --   85.25-101.00 -49.76  104
 11  \w     40.00  90.00   0.50    0.08    --   82.29 -95.00  60.00  100
 12  \w     40.00  90.00   0.50    0.08    --   82.29 -95.00 120.00  100
 13  \w     40.00  90.00   0.50    0.08    --   82.29 -95.00 150.00  100
 14  \w     40.00  90.00   0.50    0.08    --   82.29 -95.00  90.00  100
 15  \w     40.00  90.00   0.50    0.08    --   82.29 -95.00   0.00  100
 16  \w     40.00  90.00   0.50    0.08    --   82.29 -95.00  30.00  100
 17  \w     46.00 133.00   0.50    0.08    --   82.29  15.00 150.00  174
 18  \w     59.00  94.00   0.50    0.08    --   46.00  52.00  89.39   70
 19  \w     31.00  60.00   0.50    0.08    --   18.00  55.00  90.45   58
 20  \w     34.00  60.00   0.50    0.08    --   22.00  59.00 -21.65   52
 21  \w     34.00  60.00   0.50    0.08    --   22.00  59.00 -61.20   52
 22  \w     30.00  56.00   0.50    0.08    --   18.00  60.00-130.79   52
 23  \w     -6.00  20.00   0.50    0.08    --  -10.00  78.00 124.77   52
 24  \w    -88.00 -14.00   0.50    0.08    --  -60.21 126.00 150.00  148
 25  \w    -92.00 -31.00   0.50    0.08    --  -76.40 112.00  90.00  122
 26  \w    -92.00 -31.00   0.50    0.08    --  -76.40 112.00   0.00  122
 27  \w    -97.00 -33.00   0.50    0.08    --  -79.50 115.00-103.23  128
 28  \w    -92.00 -31.00   0.50    0.08    --  -76.40 112.00-150.00  122
 29  \w    -92.00 -35.00   0.50    0.08    --  -79.50 102.00-165.41  114
 30  \w    -97.00 -33.00   0.50    0.08    --  -79.50 115.00 -75.46  128
 31  \w    -97.00 -33.00   0.50    0.08    --  -79.50 115.00   8.89  128
 32  \w    -97.00 -33.00   0.50    0.08    --  -79.50 115.00-103.23  128
 33  \w    -97.00 -33.00   0.50    0.08    --  -79.50 117.00  82.77  128
 34  \w    -97.00 -22.00   0.50    0.08    --  -69.63 126.00  90.00  150
 35  \w   -116.00 -78.00   0.50    0.08    --  -66.00 -42.00 -86.79   76
 36  \w   -116.00 -79.00   0.50    0.08    --  -66.00 -44.00-163.63   74
 37  \w   -122.00 -87.00   0.50    0.08    --  -74.00 -54.00-105.90   70
 38  \w   -116.00 -85.00   0.50    0.08    --  -70.00 -59.00 -34.58   62
 39  \w   -106.00 -71.00   0.50    0.08    --  -58.00 -52.00  35.54   70
 40  \w   -111.00 -76.00   0.50    0.08    --  -62.00 -49.00 123.29   70
 41  \w    -99.00 -64.00   0.50    0.08    --  -50.00 -47.00 144.99   70
 42  \w   -121.00 -86.00   0.50    0.08    --  -74.00 -55.00 116.02   70
 43  \w   -124.00 -92.00   0.50    0.08    --  -79.50 -63.00 110.10   64
 44  \w   -121.00 -86.00   0.50    0.08    --  -74.00 -58.00  71.95   70
 45  \w   -121.00 -86.00   0.50    0.08    --  -74.00 -56.00  20.72   70
 46  \w   -130.00 -91.00   0.50    0.08    --  -79.50 -40.00 -13.46   78
 47  \w   -121.00 -86.00   0.50    0.08    --  -74.00 -55.00 -45.29   70
 48  \w   -130.00 -91.00   0.50    0.08    --  -79.50 -41.00-111.53   78
 49  \w   -120.00 -86.00   0.50    0.08    --  -74.00 -59.00-164.06   68
 50  \w   -126.00 -93.00   0.50    0.08    --  -79.50-120.00-156.50   66
 51  \w   -126.00 -93.00   0.50    0.08    --  -79.50-121.00 -71.20   66
 52  \w   -125.00 -91.00   0.50    0.08    --  -79.50 -60.00-142.84   68
 53  \w   -124.00 -90.00   0.50    0.08    --  -78.00 -59.00 -77.44   68
 54  \w   -120.00 -86.00   0.50    0.08    --  -74.00 -59.00 -23.14   68
 55  \w   -125.00 -90.00   0.50    0.08    --  -78.00 -57.00  50.48   70
 56  \w   -126.00 -92.00   0.50    0.08    --  -79.50-123.00 142.98   68
 57  \w   -126.00 -92.00   0.50    0.08    --  -79.50-123.00 175.57   68
 58  \w   -126.00 -92.00   0.50    0.08    --  -79.50-123.00  87.50   68
 59  \w   -126.00 -93.00   0.50    0.08    --  -79.50-120.00  47.72   66
 60  \w   -127.00 -90.00   0.50    0.08    --  -79.50-126.00  21.60   74
 61  \w   -126.00 -92.00   0.50    0.08    --  -79.50-122.00 107.21   68
 62  \w   -125.00 -91.00   0.50    0.08    --  -79.50 -60.00 171.26   68
 63  \w   -127.00 -90.00   0.50    0.08    --  -79.50-127.00 -30.07   74
 64  \w   -125.00 -90.00   0.50    0.08    --  -79.50 -62.00 -57.48   70
 65  \w   -126.00 -93.00   0.50    0.08    --  -79.50-120.00-133.11   66
 66  \w   -127.00 -91.00   0.50    0.08    --  -79.50 -56.00-121.66   72
;
_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      0.1078396000
_diffrn_orient_matrix_UB_12      -0.0236198000
_diffrn_orient_matrix_UB_13      -0.0144033000
_diffrn_orient_matrix_UB_21      -0.0388025000
_diffrn_orient_matrix_UB_22      0.0319803000
_diffrn_orient_matrix_UB_23      -0.1052442000
_diffrn_orient_matrix_UB_31      0.0410778000
_diffrn_orient_matrix_UB_32      0.0924180000
_diffrn_orient_matrix_UB_33      0.0328376000
_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  0.0682
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            63395
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.657
_diffrn_reflns_theta_min         2.887
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    3.290
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.507
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024) 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    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_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          0.380
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.065
_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     457
_refine_ls_number_reflns         5633
_refine_ls_number_restraints     594
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0976P)^2^+1.5458P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1638
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4908
_reflns_number_total             5633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           4-K
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_original_cell_volume        2802.29(7)
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               1574511
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.368
_shelx_estimated_absorpt_t_max   0.574
_shelx_res_checksum              10817
_shelx_hkl_checksum              99097