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_1574516
_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         'C50 H68 B2 Li2 N4 O4'
_chemical_formula_sum            'C50 H68 B2 Li2 N4 O4'
_chemical_formula_weight         824.58
_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             2023-12-08
_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                89.4930(10)
_cell_angle_beta                 81.2150(10)
_cell_angle_gamma                81.4630(10)
_cell_formula_units_Z            3
_cell_length_a                   12.12980(10)
_cell_length_b                   14.7250(2)
_cell_length_c                   19.7956(2)
_cell_measurement_reflns_used    36049
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.1900
_cell_measurement_theta_min      3.7380
_cell_volume                     3455.18(7)
_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 0.993
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -99.00 -64.00   0.50    0.35    --  -50.00 -50.00-120.99   70
  2  \w   -103.00 -68.00   0.50    0.35    --  -54.00 -50.00 122.85   70
  3  \w   -103.00 -68.00   0.50    0.35    --  -54.00 -48.00 159.52   70
  4  \w     15.00  66.00   0.50    0.35    --   58.17 -95.00-120.00  102
  5  \w     15.00  66.00   0.50    0.35    --   58.17 -95.00  30.00  102
  6  \w   -112.00 -75.00   0.50    0.35    --  -62.00 -44.00  47.15   74
  7  \w   -115.00 -80.00   0.50    0.35    --  -66.00 -48.00 102.06   70
  8  \w   -117.00 -84.00   0.50    0.35    --  -70.00 -57.00 -23.84   66
  9  \w   -119.00 -84.00   0.50    0.35    --  -70.00 -47.00  25.06   70
 10  \w     32.00  98.00   0.50    1.39    --   78.00-117.00 114.69  132
 11  \w    -97.00 -32.00   0.50    1.39    --  -78.00 114.00 -98.84  130
 12  \w   -126.00 -91.00   0.50    1.39    --  -78.00 -52.00 -96.10   70
 13  \w    -97.00 -32.00   0.50    1.39    --  -78.00 114.00 -80.44  130
 14  \w   -124.00 -95.00   0.50    1.39    --  -79.50 -65.00 164.89   58
 15  \w   -132.00 -90.00   0.50    1.39    --  -79.50 -31.00-148.27   84
 16  \w   -126.00 -91.00   0.50    1.39    --  -79.50-125.00 -44.01   70
 17  \w   -126.00 -91.00   0.50    1.39    --  -79.50-124.00  37.54   70
 18  \w    -98.00 -33.00   0.50    1.39    --  -79.50 119.00 -39.21  130
 19  \w    -93.00 -34.00   0.50    1.39    --  -79.50 112.00  37.89  118
 20  \w   -125.00 -94.00   0.50    1.39    --  -79.50-119.00 158.77   62
 21  \w    -97.00 -33.00   0.50    1.39    --  -79.50 117.00 160.19  128
 22  \w    -97.00 -33.00   0.50    1.39    --  -79.50 117.00-174.52  128
 23  \w   -126.00 -92.00   0.50    1.39    --  -79.50-122.00-120.37   68
 24  \w   -125.00 -97.00   0.50    1.39    --  -79.50-114.00-177.01   56
 25  \w   -128.00 -93.00   0.50    1.39    --  -79.50 -52.00 114.46   70
 26  \w   -123.00 -97.00   0.50    1.39    --  -79.50 -66.00-122.25   52
 27  \w   -130.00 -91.00   0.50    1.39    --  -79.50 -39.00 119.57   78
 28  \w   -128.00 -93.00   0.50    1.39    --  -79.50 -49.00-172.00   70
 29  \w    -97.00 -33.00   0.50    1.39    --  -79.50 115.00 -43.64  128
 30  \w    -97.00 -33.00   0.50    1.39    --  -79.50 116.00 131.96  128
 31  \w     40.00  90.00   0.50    1.39    --   82.23 -95.00-120.00  100
 32  \w     40.00  90.00   0.50    1.39    --   82.23 -95.00  60.00  100
 33  \w     46.00 133.00   0.50    1.39    --   82.23  15.00-180.00  174
 34  \w     40.00  90.00   0.50    1.39    --   82.23 -95.00   0.00  100
 35  \w     40.00  90.00   0.50    1.39    --   82.23 -95.00 -30.00  100
 36  \w     40.00  90.00   0.50    1.39    --   82.23 -95.00 -60.00  100
 37  \w     37.00  92.00   0.50    1.39    --   82.23-112.00  90.00  110
 38  \w     37.00  92.00   0.50    1.39    --   82.23-112.00 120.00  110
 39  \w     40.00  90.00   0.50    1.39    --   82.23 -95.00  30.00  100
 40  \w     40.00  90.00   0.50    1.39    --   82.23 -95.00-150.00  100
 41  \w     37.00  92.00   0.50    1.39    --   82.23-112.00   0.00  110
 42  \w     42.00  93.00   0.50    1.39    --   85.25 -97.00 129.94  102
 43  \w     38.00  99.00   0.50    1.39    --   85.25-122.00  75.39  122
 44  \w     43.00  92.00   0.50    1.39    --   85.25 -94.00 165.82   98
 45  \w     62.00 136.00   0.50    1.39    --   85.25  16.00-112.07  148
 46  \w     99.00 135.00   0.50    1.39    --   85.25  46.00 -91.56   72
 47  \w     38.00  98.00   0.50    1.39    --   85.25-120.00 146.38  120
 48  \w     98.00 133.00   0.50    1.39    --   85.25  54.00  -5.84   70
 49  \w     98.00 132.00   0.50    1.39    --   85.25 122.00-167.38   68
 50  \w     43.00  92.00   0.50    1.39    --   85.25 -94.00 134.11   98
 51  \w     42.00  93.00   0.50    1.39    --   85.25 -97.00 -84.47  102
 52  \w     50.00 135.00   0.50    1.39    --   85.25  14.00  -0.81  170
 53  \w     98.00 135.00   0.50    1.39    --   85.25  44.00  66.14   74
 54  \w     34.00  60.00   0.50    0.35    --   22.00  59.00  19.66   52
 55  \w     34.00  60.00   0.50    0.35    --   22.00  59.00 -23.84   52
 56  \w     34.00  60.00   0.50    0.35    --   22.00  58.00-147.33   52
 57  \w     34.00  60.00   0.50    0.35    --   22.00  59.00 -58.17   52
 58  \w     34.00  60.00   0.50    0.35    --   22.00  59.00  61.14   52
 59  \w     34.00  60.00   0.50    0.35    --   22.00  58.00 101.32   52
 60  \w   -121.00 -86.00   0.50    1.39    --  -74.00 -57.00  -4.01   70
 61  \w   -122.00 -87.00   0.50    1.39    --  -74.00 -54.00  88.63   70
 62  \w   -122.00 -87.00   0.50    1.39    --  -74.00 -54.00  23.59   70
 63  \w   -121.00 -86.00   0.50    1.39    --  -74.00 -58.00 -35.75   70
 64  \w   -122.00 -87.00   0.50    1.39    --  -74.00 -53.00 -55.07   70
 65  \w   -121.00 -86.00   0.50    1.39    --  -74.00 -56.00   7.17   70
 66  \w   -121.00 -86.00   0.50    1.39    --  -74.00 -58.00-126.90   70
 67  \w   -120.00 -86.00   0.50    1.39    --  -74.00 -59.00-153.28   68
 68  \w   -121.00 -86.00   0.50    1.39    --  -74.00 -55.00 -73.97   70
 69  \w   -125.00 -90.00   0.50    1.39    --  -78.00 -55.00 170.37   70
 70  \w   -125.00 -90.00   0.50    1.39    --  -79.50 -62.00  57.94   70
 71  \w   -126.00 -93.00   0.50    1.39    --  -79.50-121.00  76.34   66
 72  \w   -126.00 -87.00   0.50    1.39    --  -79.50-132.00 118.90   78
 73  \w   -126.00 -91.00   0.50    1.39    --  -79.50 -58.00  80.52   70
 74  \w   -126.00 -86.00   0.50    1.39    --  -79.50-135.00 144.43   80
 75  \w   -126.00 -93.00   0.50    1.39    --  -79.50-120.00  -9.93   66
 76  \w   -126.00 -85.00   0.50    1.39    --  -79.50-137.00  21.16   82
 77  \w    102.00 131.00   0.50    1.39    --   85.25 115.00  34.59   58
;
_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      0.1133240000
_diffrn_orient_matrix_UB_12      -0.0373411000
_diffrn_orient_matrix_UB_13      0.0234503000
_diffrn_orient_matrix_UB_21      0.0635767000
_diffrn_orient_matrix_UB_22      0.0307940000
_diffrn_orient_matrix_UB_23      -0.0676915000
_diffrn_orient_matrix_UB_31      0.0024133000
_diffrn_orient_matrix_UB_32      0.0940857000
_diffrn_orient_matrix_UB_33      0.0327155000
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            95176
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.377
_diffrn_reflns_theta_min         3.035
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       block
_exptl_crystal_F_000             1332
_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          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1075
_refine_ls_number_reflns         13797
_refine_ls_number_restraints     2003
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0768
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1579P)^2^+0.9018P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2162
_refine_ls_wR_factor_ref         0.2279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11089
_reflns_number_total             13797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           6-Li_THF
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_database_code               1574516
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.857
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              36378
_shelx_hkl_checksum              35143