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_1574518
_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 N8 Na4'
_chemical_formula_sum            'C68 H72 B4 N8 Na4'
_chemical_formula_weight         1136.53
_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             2023-12-15
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.53180(10)
_cell_length_b                   22.53180(10)
_cell_length_c                   24.21670(10)
_cell_measurement_reflns_used    116636
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.2130
_cell_measurement_theta_min      2.6640
_cell_volume                     12294.38(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_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 2014/5 (Sheldrick, 2014)''
_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 0.984
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     13.00  75.00   0.50    3.31    --   58.45-108.00 -38.00  124
  2  \w    -76.00 -15.00   0.50    3.31    --  -60.36 108.00  59.00  122
  3  \w    -86.00 -25.00   0.50    3.31    --  -69.85 108.00  59.00  122
  4  \w     26.00  87.00   0.50    3.31    --   71.26-108.00 -38.00  122
  5  \w    -92.00 -31.00   0.50    3.31    --  -76.37 108.00  59.00  122
  6  \w     37.00  92.00   0.50    3.31    --   82.26-108.00 -38.00  110
  7  \w     51.00  86.00   0.50    3.31    --   38.00  52.00-148.09   70
  8  \w     59.00  94.00   0.50    3.31    --   46.00  52.00-109.17   70
  9  \w   -102.00 -67.00   0.50    3.31    --  -54.00 -52.00  -3.08   70
 10  \w   -109.00 -69.00   0.50    3.31    --  -58.00 -37.00 121.09   80
 11  \w   -111.00 -76.00   0.50    3.31    --  -62.00 -48.00 -37.19   70
 12  \w   -115.00 -80.00   0.50    3.31    --  -66.00 -47.00-121.80   70
 13  \w   -116.00 -85.00   0.50    3.31    --  -70.00 -59.00-156.16   62
 14  \w   -117.00 -83.00   0.50    3.31    --  -70.00 -56.00 112.23   68
 15  \w   -124.00 -87.00   0.50    3.31    --  -74.00 -44.00 -68.67   74
 16  \w   -121.00 -86.00   0.50    3.31    --  -74.00 -58.00  60.62   70
 17  \w    -92.00 -31.00   0.50    3.31    --  -76.37 112.00 150.00  122
 18  \w    -92.00 -31.00   0.50    3.31    --  -76.37 112.00 -90.00  122
 19  \w    -92.00 -31.00   0.50    3.31    --  -76.37 112.00   0.00  122
 20  \w    -97.00 -32.00   0.50    3.31    --  -78.00 114.00-132.12  130
 21  \w    -97.00 -32.00   0.50    3.31    --  -78.00 114.00 117.51  130
 22  \w   -130.00 -91.00   0.50    3.31    --  -79.50 -41.00 -45.36   78
 23  \w   -126.00 -93.00   0.50    3.31    --  -79.50-121.00-148.98   66
 24  \w   -128.00 -93.00   0.50    3.31    --  -79.50 -50.00 105.03   70
 25  \w   -126.00 -92.00   0.50    3.31    --  -79.50-122.00 -62.64   68
 26  \w    -97.00 -33.00   0.50    3.31    --  -79.50 115.00 -26.90  128
 27  \w   -124.00 -92.00   0.50    3.31    --  -79.50 -63.00-102.99   64
 28  \w   -126.00 -92.00   0.50    3.31    --  -79.50-122.00 148.53   68
 29  \w   -126.00 -93.00   0.50    3.31    --  -79.50-121.00  83.20   66
 30  \w   -128.00 -93.00   0.50    3.31    --  -79.50 -49.00  41.39   70
 31  \w   -129.00 -93.00   0.50    3.31    --  -79.50 -48.00-105.90   72
 32  \w   -124.00 -92.00   0.50    3.31    --  -79.50 -63.00-128.93   64
 33  \w   -125.00 -91.00   0.50    3.31    --  -79.50 -60.00  55.67   68
 34  \w   -126.00 -93.00   0.50    3.31    --  -79.50-120.00  -4.65   66
 35  \w   -128.00 -93.00   0.50    3.31    --  -79.50 -50.00   3.20   70
 36  \w   -101.00 -33.00   0.50    3.31    --  -79.50 125.00  27.66  136
 37  \w   -125.00 -91.00   0.50    3.31    --  -79.50 -60.00 128.54   68
 38  \w   -130.00 -91.00   0.50    3.31    --  -79.50 -39.00 174.01   78
 39  \w     40.00  90.00   0.50    3.31    --   82.26 -95.00  30.00  100
 40  \w     40.00  90.00   0.50    3.31    --   82.26 -95.00  60.00  100
 41  \w     40.00  90.00   0.50    3.31    --   82.26 -95.00 150.00  100
 42  \w     40.00  90.00   0.50    3.31    --   82.26 -95.00 120.00  100
 43  \w     40.00  90.00   0.50    3.31    --   82.26 -95.00 -60.00  100
 44  \w     40.00  90.00   0.50    3.31    --   82.26 -95.00   0.00  100
 45  \w     40.00  90.00   0.50    3.31    --   82.26 -95.00  90.00  100
 46  \w     40.00  90.00   0.50    3.31    --   82.26 -95.00-180.00  100
 47  \w     46.00 133.00   0.50    3.31    --   82.26  15.00 -30.00  174
 48  \w     37.00  93.00   0.50    3.31    --   82.26-112.00 -90.00  112
 49  \w     46.00 133.00   0.50    3.31    --   82.26  15.00 -30.00  174
 50  \w     42.00  93.00   0.50    3.31    --   85.25 -98.00 -17.12  102
 51  \w     67.00 136.00   0.50    3.31    --   85.25  18.00-141.89  138
 52  \w     42.00  93.00   0.50    3.31    --   85.25 -98.00-115.60  102
 53  \w     42.00  93.00   0.50    3.31    --   85.25 -97.00-146.35  102
 54  \w    -26.00   2.00   0.50    3.31    --  -14.00 102.00 126.13   56
 55  \w     30.00  56.00   0.50    3.31    --   18.00  60.00 120.03   52
 56  \w     30.00  56.00   0.50    3.31    --   18.00  60.00   5.98   52
 57  \w     34.00  60.00   0.50    3.31    --   22.00  59.00  46.65   52
 58  \w     34.00  60.00   0.50    3.31    --   22.00  58.00 -62.54   52
 59  \w     34.00  60.00   0.50    3.31    --   22.00  59.00 175.47   52
 60  \w    -86.00 -51.00   0.50    3.31    --  -38.00 -51.00  49.79   70
 61  \w     55.00  90.00   0.50    3.31    --   42.00  52.00 -55.41   70
 62  \w   -121.00 -91.00   0.50    3.31    --  -74.00 -58.00  84.56   60
 63  \w   -126.00 -93.00   0.50    3.31    --  -79.50-120.00-102.33   66
 64  \w   -126.00 -92.00   0.50    3.31    --  -79.50-123.00 114.66   68
 65  \w   -126.00 -93.00   0.50    3.31    --  -79.50-120.00  24.79   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      -0.0197003000
_diffrn_orient_matrix_UB_12      0.0057387000
_diffrn_orient_matrix_UB_13      0.0606910000
_diffrn_orient_matrix_UB_21      0.0529929000
_diffrn_orient_matrix_UB_22      0.0413828000
_diffrn_orient_matrix_UB_23      0.0114915000
_diffrn_orient_matrix_UB_31      -0.0384583000
_diffrn_orient_matrix_UB_32      0.0541136000
_diffrn_orient_matrix_UB_33      -0.0152351000
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            291514
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.061
_diffrn_reflns_theta_min         2.679
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021) 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            'translucent colourless'
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       plate
_exptl_crystal_F_000             4800
_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          0.110
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.50(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     774
_refine_ls_number_reflns         12558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0582P)^2^+2.3825P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                11668
_reflns_number_total             12558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           6-Na
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_original_cell_volume        12294.38(12)
_cod_database_code               1574518
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              27924
_shelx_hkl_checksum              80220