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_1574520
_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_absolute_configuration unk
_chemical_formula_moiety         'C68 H72 B4 K4 N8'
_chemical_formula_sum            'C68 H72 B4 K4 N8'
_chemical_formula_weight         1200.97
_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_Hall           'P -4 2n'
_space_group_name_H-M_alt        'P -4 21 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-11-22
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.279
_cell_length_b                   22.279
_cell_length_c                   25.81660(10)
_cell_measurement_reflns_used    197138
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0510
_cell_measurement_theta_min      2.5780
_cell_volume                     12814.17(5)
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     26.00  56.00   0.50    0.05    --   14.00  60.00-120.71   60
  2  \w     34.00  60.00   0.50    0.05    --   22.00  58.00 -65.65   52
  3  \w     30.00  56.00   0.50    0.05    --   18.00  60.00 -12.19   52
  4  \w     30.00  56.00   0.50    0.05    --   18.00  60.00  35.14   52
  5  \w     30.00  56.00   0.50    0.05    --   18.00  60.00 118.89   52
  6  \w     59.00  94.00   0.50    0.05    --   46.00  52.00 -17.35   70
  7  \w     98.00 133.00   0.50    0.05    --   85.25  53.00  11.71   70
  8  \w     98.00 135.00   0.50    0.05    --   85.25  45.00 -22.47   74
  9  \w    101.00 132.00   0.50    0.05    --   85.25 117.00-123.80   62
 10  \w     73.00 137.00   0.50    0.05    --   85.25  21.00 -80.56  128
 11  \w     39.00  98.00   0.50    0.05    --   85.25-117.00 121.35  118
 12  \w     37.00  93.00   0.50    0.05    --   82.26-112.00 150.00  112
 13  \w     36.00  97.00   0.50    0.05    --   82.26-115.00  34.00  122
 14  \w     13.00  79.00   0.50    0.05    --   58.45-115.00  34.00  132
 15  \w     25.00  72.00   0.50    0.05    --   71.26-115.00  34.00   94
 16  \w     42.00  93.00   0.50    0.05    --   85.25 -98.00  51.53  102
 17  \w     42.00  93.00   0.50    0.05    --   85.25 -97.00   0.48  102
 18  \w     43.00  92.00   0.50    0.05    --   85.25 -95.00  77.38   98
 19  \w     40.00  97.00   0.50    0.05    --   85.25-114.00-107.46  114
 20  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00-150.00  100
 21  \w     42.00  93.00   0.50    0.05    --   85.25 -98.00-159.13  102
 22  \w     42.00  93.00   0.50    0.05    --   85.25 -97.00 -98.45  102
 23  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 -60.00  100
 24  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 -30.00  100
 25  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 120.00  100
 26  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 150.00  100
 27  \w    -96.00 -58.00   0.50    0.05    --  -46.00 -43.00 163.45   76
 28  \w    -86.00 -51.00   0.50    0.05    --  -38.00 -51.00 116.50   70
 29  \w   -124.00 -94.00   0.50    0.05    --  -79.50 -64.00 168.25   60
 30  \w   -124.00 -89.00   0.50    0.05    --  -78.00 -61.00 133.74   70
 31  \w   -124.00 -92.00   0.50    0.05    --  -79.50 -63.00  68.71   64
 32  \w   -124.00 -92.00   0.50    0.05    --  -79.50 -63.00  78.70   64
 33  \w    -94.00 -59.00   0.50    0.05    --  -46.00 -51.00  23.63   70
 34  \w   -121.00 -86.00   0.50    0.05    --  -74.00 -56.00 171.33   70
 35  \w   -116.00 -85.00   0.50    0.05    --  -70.00 -59.00 -26.70   62
 36  \w   -117.00 -83.00   0.50    0.05    --  -70.00 -56.00 -57.76   68
 37  \w   -125.00 -90.00   0.50    0.05    --  -78.00 -58.00-162.64   70
 38  \w   -121.00 -86.00   0.50    0.05    --  -74.00 -55.00-129.37   70
 39  \w   -124.00 -94.00   0.50    0.05    --  -79.50 -64.00 -60.08   60
 40  \w   -107.00 -72.00   0.50    0.05    --  -58.00 -50.00  -6.87   70
 41  \w   -107.00 -72.00   0.50    0.05    --  -58.00 -49.00  72.83   70
 42  \w   -127.00 -92.00   0.50    0.05    --  -79.50 -55.00 121.50   70
 43  \w   -122.00 -87.00   0.50    0.05    --  -74.00 -54.00 123.47   70
 44  \w   -126.00 -91.00   0.50    0.05    --  -78.00 -54.00 107.60   70
 45  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -49.00  28.93   70
 46  \w   -116.00 -79.00   0.50    0.05    --  -66.00 -45.00 -93.74   74
 47  \w   -111.00 -76.00   0.50    0.05    --  -62.00 -47.00-121.72   70
 48  \w   -126.00 -87.00   0.50    0.05    --  -79.50-133.00  23.36   78
 49  \w   -126.00 -93.00   0.50    0.05    --  -79.50-121.00  56.54   66
 50  \w   -126.00 -92.00   0.50    0.05    --  -79.50-123.00 -36.96   68
 51  \w   -126.00 -93.00   0.50    0.05    --  -79.50-121.00 -72.35   66
 52  \w   -126.00 -88.00   0.50    0.05    --  -79.50-130.00-105.41   76
 53  \w   -126.00 -92.00   0.50    0.05    --  -79.50-123.00-132.80   68
 54  \w   -126.00 -93.00   0.50    0.05    --  -79.50-121.00-152.18   66
 55  \w   -126.00 -93.00   0.50    0.05    --  -79.50-120.00  79.61   66
 56  \w   -126.00 -93.00   0.50    0.05    --  -79.50-121.00 138.42   66
 57  \w   -126.00 -93.00   0.50    0.05    --  -79.50-120.00 115.27   66
 58  \w   -104.00 -33.00   0.50    0.05    --  -79.50 133.00-102.61  142
 59  \w    -97.00 -32.00   0.50    0.05    --  -78.00 114.00-174.18  130
 60  \w    -97.00 -32.00   0.50    0.05    --  -78.00 114.00  -2.72  130
 61  \w    -92.00 -31.00   0.50    0.05    --  -76.37 112.00  60.00  122
 62  \w    -90.00 -24.00   0.50    0.05    --  -69.85 115.00 123.00  132
 63  \w    -81.00 -14.00   0.50    0.05    --  -60.36 115.00 123.00  134
 64  \w    -97.00 -30.00   0.50    0.05    --  -76.37 115.00 123.00  134
 65  \w    -92.00 -31.00   0.50    0.05    --  -76.37 112.00-120.00  122
 66  \w    -31.00  -4.00   0.50    0.05    --  -14.00 110.00-132.66   54
;
_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      -0.0640867000
_diffrn_orient_matrix_UB_12      -0.0226568000
_diffrn_orient_matrix_UB_13      -0.0109564000
_diffrn_orient_matrix_UB_21      0.0156838000
_diffrn_orient_matrix_UB_22      -0.0068530000
_diffrn_orient_matrix_UB_23      -0.0578133000
_diffrn_orient_matrix_UB_31      0.0206863000
_diffrn_orient_matrix_UB_32      -0.0649678000
_diffrn_orient_matrix_UB_33      0.0099054000
_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  0.0418
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            294467
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.307
_diffrn_reflns_theta_min         2.620
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    2.829
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.315
_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    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             5056
_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          0.430
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.447(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     774
_refine_ls_number_reflns         13124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0391P)^2^+2.6663P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0703
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                12879
_reflns_number_total             13124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           6-K
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_database_code               1574520
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.376
_shelx_estimated_absorpt_t_max   0.516
_shelx_res_checksum              31154
_shelx_hkl_checksum              69411