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_1574517
_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         'C46 H44 B4 N4 O4, 3(C6 H6)'
_chemical_formula_sum            'C64 H62 B4 N4 O4'
_chemical_formula_weight         994.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-12-07
_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                90
_cell_angle_beta                 110.6070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.94100(10)
_cell_length_b                   18.70160(10)
_cell_length_c                   20.44820(10)
_cell_measurement_reflns_used    47394
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.3180
_cell_measurement_theta_min      3.1350
_cell_volume                     5348.07(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     34.00  60.00   0.50    0.36    --   22.00  59.00  37.29   52
  2  \w     25.00  54.00   0.50    0.36    --   14.00  61.00 173.48   58
  3  \w     34.00  60.00   0.50    0.36    --   22.00  59.00  79.61   52
  4  \w     34.00  60.00   0.50    0.36    --   22.00  58.00   0.86   52
  5  \w     30.00  60.00   0.50    0.36    --   18.00  59.00 -34.60   60
  6  \w     34.00  60.00   0.50    0.36    --   22.00  59.00-112.74   52
  7  \w     34.00  60.00   0.50    0.36    --   22.00  58.00-156.52   52
  8  \w     34.00  60.00   0.50    0.36    --   22.00  57.00 -74.38   52
  9  \w     59.00  94.00   0.50    0.36    --   46.00  52.00  83.71   70
 10  \w     40.00  76.00   0.50    0.36    --   26.00  47.00 133.39   72
 11  \w     46.00 133.00   0.50    0.36    --   82.26  15.00  30.00  174
 12  \w     99.00 134.00   0.50    0.36    --   85.25  52.00  81.61   70
 13  \w    103.00 131.00   0.50    0.36    --   85.25 114.00 152.62   56
 14  \w     42.00  93.00   0.50    0.36    --   85.25 -98.00   1.20  102
 15  \w     40.00  90.00   0.50    0.36    --   82.26 -95.00 -30.00  100
 16  \w     40.00  90.00   0.50    0.36    --   82.26 -95.00 -60.00  100
 17  \w     40.00  90.00   0.50    0.36    --   82.26 -95.00-120.00  100
 18  \w     40.00  90.00   0.50    0.36    --   82.26 -95.00-180.00  100
 19  \w     40.00  90.00   0.50    0.36    --   82.26 -95.00-150.00  100
 20  \w     40.00  90.00   0.50    0.36    --   82.26 -95.00 -90.00  100
 21  \w     40.00  90.00   0.50    0.36    --   82.26 -95.00  30.00  100
 22  \w     40.00  90.00   0.50    0.36    --   82.26 -95.00  60.00  100
 23  \w     40.00  89.00   0.50    0.36    --   82.26 -94.00  70.00   98
 24  \w     29.00  78.00   0.50    0.36    --   71.26 -94.00  70.00   98
 25  \w     43.00  92.00   0.50    0.36    --   85.25 -94.00  90.03   98
 26  \w     42.00  93.00   0.50    0.36    --   85.25 -97.00 118.50  102
 27  \w     16.00  65.00   0.50    0.36    --   58.45 -94.00  70.00   98
 28  \w     -4.00  22.00   0.50    0.36    --  -10.00  76.00 174.07   52
 29  \w    -97.00 -33.00   0.50    0.36    --  -79.50 115.00 104.43  128
 30  \w    -97.00 -32.00   0.50    0.36    --  -78.00 114.00   0.05  130
 31  \w    -97.00 -32.00   0.50    0.36    --  -78.00 114.00 -68.61  130
 32  \w    -96.00 -34.00   0.50    0.36    --  -79.50 114.00-107.22  124
 33  \w    -77.00 -27.00   0.50    0.36    --  -69.85  94.00-178.00  100
 34  \w    -92.00 -35.00   0.50    0.36    --  -79.50 102.00-155.44  114
 35  \w    -83.00 -34.00   0.50    0.36    --  -76.37  94.00-178.00   98
 36  \w    -67.00 -18.00   0.50    0.36    --  -60.36  94.00-178.00   98
 37  \w    -99.00 -64.00   0.50    0.36    --  -50.00 -48.00 -67.19   70
 38  \w   -120.00 -86.00   0.50    0.36    --  -74.00 -60.00 -59.65   68
 39  \w   -124.00 -92.00   0.50    0.36    --  -79.50 -63.00  22.85   64
 40  \w   -120.00 -86.00   0.50    0.36    --  -74.00 -59.00  66.01   68
 41  \w    -87.00 -52.00   0.50    0.36    --  -38.00 -50.00 119.58   70
 42  \w    -94.00 -59.00   0.50    0.36    --  -46.00 -51.00 165.36   70
 43  \w   -124.00 -92.00   0.50    0.36    --  -79.50 -63.00 158.88   64
 44  \w   -116.00 -85.00   0.50    0.36    --  -70.00 -59.00 127.93   62
 45  \w   -117.00 -85.00   0.50    0.36    --  -70.00 -58.00 108.61   64
 46  \w   -121.00 -86.00   0.50    0.36    --  -74.00 -55.00 163.85   70
 47  \w   -125.00 -90.00   0.50    0.36    --  -78.00 -57.00 103.29   70
 48  \w   -117.00 -85.00   0.50    0.36    --  -70.00 -58.00  43.70   64
 49  \w   -122.00 -87.00   0.50    0.36    --  -74.00 -54.00-108.07   70
 50  \w   -102.00 -67.00   0.50    0.36    --  -54.00 -52.00 -85.64   70
 51  \w   -106.00 -71.00   0.50    0.36    --  -58.00 -52.00-120.71   70
 52  \w   -122.00 -87.00   0.50    0.36    --  -74.00 -54.00-136.56   70
 53  \w   -121.00 -86.00   0.50    0.36    --  -74.00 -57.00-173.87   70
 54  \w   -126.00 -91.00   0.50    0.36    --  -79.50 -58.00-150.79   70
 55  \w   -122.00 -87.00   0.50    0.36    --  -74.00 -52.00 -25.15   70
 56  \w   -128.00 -93.00   0.50    0.36    --  -79.50 -52.00  -5.52   70
 57  \w   -128.00 -93.00   0.50    0.36    --  -79.50 -49.00  45.82   70
 58  \w   -115.00 -80.00   0.50    0.36    --  -66.00 -49.00  71.03   70
 59  \w   -102.00 -67.00   0.50    0.36    --  -54.00 -52.00  -5.88   70
 60  \w   -131.00 -65.00   0.50    0.36    --  -79.50 -19.00-141.34  132
 61  \w   -130.00 -91.00   0.50    0.36    --  -79.50 -39.00-149.70   78
 62  \w   -128.00 -93.00   0.50    0.36    --  -79.50 -49.00-178.41   70
 63  \w   -125.00 -97.00   0.50    0.36    --  -79.50-113.00-152.52   56
 64  \w   -126.00 -87.00   0.50    0.36    --  -79.50-132.00 -27.58   78
 65  \w   -127.00 -90.00   0.50    0.36    --  -79.50-126.00  -0.32   74
 66  \w   -126.00 -93.00   0.50    0.36    --  -79.50-121.00 -60.23   66
 67  \w   -126.00 -92.00   0.50    0.36    --  -79.50-123.00  18.14   68
 68  \w   -126.00 -93.00   0.50    0.36    --  -79.50-121.00  85.48   66
 69  \w   -126.00 -92.00   0.50    0.36    --  -79.50-122.00 112.30   68
 70  \w   -126.00 -92.00   0.50    0.36    --  -79.50-123.00 179.24   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      -0.0280215000
_diffrn_orient_matrix_UB_12      0.0685725000
_diffrn_orient_matrix_UB_13      -0.0442994000
_diffrn_orient_matrix_UB_21      0.0714709000
_diffrn_orient_matrix_UB_22      0.0431645000
_diffrn_orient_matrix_UB_23      0.0599176000
_diffrn_orient_matrix_UB_31      0.0790081000
_diffrn_orient_matrix_UB_32      -0.0147964000
_diffrn_orient_matrix_UB_33      -0.0304334000
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            121072
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.701
_diffrn_reflns_theta_min         3.191
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.772
_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            yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2104
_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
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     693
_refine_ls_number_reflns         10749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0480P)^2^+1.8093P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0996
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9389
_reflns_number_total             10749
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           6-BCat
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1574517
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              70803
_shelx_hkl_checksum              77550