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_1574510
_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         'C35 H41 B3 Li N7 O3'
_chemical_formula_sum            'C35 H41 B3 Li N7 O3'
_chemical_formula_weight         647.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-12-02
_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                 118.0980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1164(2)
_cell_length_b                   12.66620(10)
_cell_length_c                   17.0662(2)
_cell_measurement_reflns_used    26628
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8460
_cell_measurement_theta_min      4.4320
_cell_volume                     3454.57(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     21.00  49.00   0.50    0.59    --   10.00  62.00 135.30   56
  2  \w     30.00  56.00   0.50    0.59    --   18.00  60.00  10.36   52
  3  \w     34.00  60.00   0.50    0.59    --   22.00  59.00 -77.48   52
  4  \w     30.00  56.00   0.50    0.59    --   18.00  60.00-108.89   52
  5  \w     30.00  56.00   0.50    0.59    --   18.00  60.00-155.56   52
  6  \w     49.00  89.00   0.50    0.59    --   38.00  35.00 -18.99   80
  7  \w     46.00 133.00   0.50    0.59    --   82.26  15.00  60.00  174
  8  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00 120.00  100
  9  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00  30.00  100
 10  \w     42.00  93.00   0.50    0.59    --   85.25 -97.00 -27.86  102
 11  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00-150.00  100
 12  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00 -60.00  100
 13  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00   0.00  100
 14  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00  60.00  100
 15  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00 150.00  100
 16  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00  90.00  100
 17  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00-120.00  100
 18  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00-180.00  100
 19  \w     43.00  91.00   0.50    0.59    --   85.25 -93.00-145.72   96
 20  \w     40.00  90.00   0.50    0.59    --   82.26 -95.00 -90.00  100
 21  \w     73.00 137.00   0.50    0.59    --   85.25  21.00 159.27  128
 22  \w   -130.00 -91.00   0.50    0.59    --  -79.50 -39.00-112.02   78
 23  \w   -120.00 -86.00   0.50    0.59    --  -74.00 -60.00-111.42   68
 24  \w   -125.00 -91.00   0.50    0.59    --  -79.50 -61.00 -66.48   68
 25  \w   -121.00 -86.00   0.50    0.59    --  -74.00 -56.00 -49.03   70
 26  \w   -117.00 -84.00   0.50    0.59    --  -70.00 -57.00 -65.87   66
 27  \w   -120.00 -86.00   0.50    0.59    --  -74.00 -60.00  58.81   68
 28  \w   -121.00 -86.00   0.50    0.59    --  -74.00 -57.00  94.49   70
 29  \w   -125.00 -91.00   0.50    0.59    --  -79.50 -60.00 122.00   68
 30  \w   -121.00 -86.00   0.50    0.59    --  -74.00 -55.00 134.25   70
 31  \w   -125.00 -90.00   0.50    0.59    --  -78.00 -55.00 163.39   70
 32  \w   -121.00 -86.00   0.50    0.59    --  -74.00 -55.00 -12.24   70
 33  \w   -102.00 -67.00   0.50    0.59    --  -54.00 -52.00 100.32   70
 34  \w   -121.00 -86.00   0.50    0.59    --  -74.00 -55.00 -24.63   70
 35  \w   -126.00 -91.00   0.50    0.59    --  -78.00 -52.00  38.42   70
 36  \w   -110.00 -75.00   0.50    0.59    --  -62.00 -51.00 -47.64   70
 37  \w   -127.00 -92.00   0.50    0.59    --  -79.50 -53.00-162.09   70
 38  \w   -102.00 -67.00   0.50    0.59    --  -54.00 -52.00-143.43   70
 39  \w   -120.00 -83.00   0.50    0.59    --  -70.00 -46.00-157.96   74
 40  \w   -122.00 -87.00   0.50    0.59    --  -74.00 -53.00 -91.31   70
 41  \w   -124.00 -87.00   0.50    0.59    --  -74.00 -45.00  -4.99   74
 42  \w   -128.00 -93.00   0.50    0.59    --  -79.50 -49.00  14.43   70
 43  \w   -129.00 -92.00   0.50    0.59    --  -79.50 -45.00  67.47   74
 44  \w   -104.00 -67.00   0.50    0.59    --  -54.00 -45.00  56.62   74
 45  \w   -101.00 -61.00   0.50    0.59    --  -50.00 -39.00   6.42   80
 46  \w    -99.00 -64.00   0.50    0.59    --  -50.00 -47.00 164.85   70
 47  \w   -111.00 -76.00   0.50    0.59    --  -62.00 -50.00 137.29   70
 48  \w   -130.00 -91.00   0.50    0.59    --  -79.50 -41.00 167.36   78
 49  \w   -126.00 -85.00   0.50    0.59    --  -79.50-137.00  28.57   82
 50  \w   -126.00 -86.00   0.50    0.59    --  -79.50-134.00 113.72   80
 51  \w   -126.00 -92.00   0.50    0.59    --  -79.50-123.00 141.35   68
 52  \w   -127.00 -89.00   0.50    0.59    --  -79.50-128.00 131.47   76
 53  \w   -126.00 -92.00   0.50    0.59    --  -79.50-122.00 -33.46   68
 54  \w   -126.00 -93.00   0.50    0.59    --  -79.50-121.00 -10.75   66
 55  \w   -126.00 -93.00   0.50    0.59    --  -79.50-120.00 -75.11   66
 56  \w   -126.00 -92.00   0.50    0.59    --  -79.50-123.00 -95.19   68
 57  \w   -126.00 -93.00   0.50    0.59    --  -79.50-121.00-157.36   66
 58  \w   -105.00 -33.00   0.50    0.59    --  -79.50 135.00-119.03  144
 59  \w    -92.00 -31.00   0.50    0.59    --  -76.37 112.00-150.00  122
 60  \w    -92.00 -31.00   0.50    0.59    --  -76.37 112.00 -30.00  122
 61  \w    -92.00 -31.00   0.50    0.59    --  -76.37 112.00  30.00  122
 62  \w    -92.00 -31.00   0.50    0.59    --  -76.37 112.00  60.00  122
 63  \w    -92.00 -31.00   0.50    0.59    --  -76.37 112.00 150.00  122
 64  \w    -97.00 -32.00   0.50    0.59    --  -78.00 114.00 122.16  130
 65  \w    -39.00  -7.00   0.50    0.59    --  -18.00 116.00 123.21   64
 66  \w    -92.00 -31.00   0.50    0.59    --  -76.37 112.00 -90.00  122
;
_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      -0.0395090000
_diffrn_orient_matrix_UB_12      -0.0688388000
_diffrn_orient_matrix_UB_13      0.0448224000
_diffrn_orient_matrix_UB_21      0.0410744000
_diffrn_orient_matrix_UB_22      -0.0987880000
_diffrn_orient_matrix_UB_23      -0.0154289000
_diffrn_orient_matrix_UB_31      0.0777648000
_diffrn_orient_matrix_UB_32      0.0172141000
_diffrn_orient_matrix_UB_33      0.0906702000
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            77907
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.104
_diffrn_reflns_theta_min         2.765
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.766
_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    1.244
_exptl_crystal_description       plate
_exptl_crystal_F_000             1368
_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          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6922
_refine_ls_number_restraints     366
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1013P)^2^+1.2617P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5676
_reflns_number_total             6922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           3_borate
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574510
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              51400
_shelx_hkl_checksum              59545