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_1574519
_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         'C68 H72 B4 Li4 N8, C6 H6, C5 H12'
_chemical_formula_sum            'C79 H90 B4 Li4 N8'
_chemical_formula_weight         1222.58
_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             2023-12-05
_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                83.0730(10)
_cell_angle_beta                 73.6780(10)
_cell_angle_gamma                66.2600(10)
_cell_formula_units_Z            2
_cell_length_a                   13.5030(2)
_cell_length_b                   14.2330(2)
_cell_length_c                   21.0535(2)
_cell_measurement_reflns_used    41323
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.8420
_cell_measurement_theta_min      3.3890
_cell_volume                     3554.45(9)
_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 0.993
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w   -127.00 -92.00   0.50    0.06    --  -79.50 -55.00 152.44   70
  2  \w   -128.00 -93.00   0.50    0.06    --  -79.50 -52.00 125.60   70
  3  \w   -122.00 -87.00   0.50    0.06    --  -74.00 -53.00   8.57   70
  4  \w    -87.00 -52.00   0.50    0.06    --  -38.00 -49.00 161.31   70
  5  \w   -102.00 -67.00   0.50    0.06    --  -54.00 -52.00 146.84   70
  6  \w   -111.00 -76.00   0.50    0.06    --  -62.00 -48.00 100.43   70
  7  \w     21.00  49.00   0.50    0.06    --   10.00  62.00-146.60   56
  8  \w     30.00  56.00   0.50    0.06    --   18.00  60.00-102.66   52
  9  \w   -121.00 -86.00   0.50    0.06    --  -74.00 -56.00  87.17   70
 10  \w   -121.00 -86.00   0.50    0.06    --  -74.00 -56.00-141.96   70
 11  \w   -120.00 -86.00   0.50    0.06    --  -74.00 -59.00 170.51   68
 12  \w   -120.00 -88.00   0.50    0.06    --  -74.00 -61.00   3.54   64
 13  \w   -121.00 -86.00   0.50    0.06    --  -74.00 -57.00 -40.83   70
 14  \w     34.00  60.00   0.50    0.06    --   22.00  58.00  -7.01   52
 15  \w   -126.00 -93.00   0.50    0.06    --  -79.50-121.00-163.70   66
 16  \w   -121.00 -86.00   0.50    0.06    --  -74.00 -58.00  29.94   70
 17  \w   -117.00 -83.00   0.50    0.06    --  -70.00 -56.00 133.86   68
 18  \w   -121.00 -86.00   0.50    0.06    --  -74.00 -58.00 -59.43   70
 19  \w   -121.00 -86.00   0.50    0.06    --  -74.00 -57.00 -86.72   70
 20  \w   -127.00 -91.00   0.50    0.06    --  -79.50 -56.00  77.26   72
 21  \w   -119.00 -84.00   0.50    0.06    --  -70.00 -47.00-173.41   70
 22  \w    -97.00 -33.00   0.50    0.06    --  -79.50 115.00-177.98  128
 23  \w     39.00 104.00   0.50    0.06    --   85.25-134.00 121.41  130
 24  \w     40.00  90.00   0.50    0.06    --   82.26 -95.00  90.00  100
 25  \w   -126.00 -85.00   0.50    0.06    --  -79.50-136.00-119.09   82
 26  \w     16.00  66.00   0.50    0.06    --   58.45 -95.00 -30.00  100
 27  \w     44.00  91.00   0.50    0.06    --   85.25 -92.00  45.30   94
 28  \w   -127.00 -90.00   0.50    0.06    --  -79.50-127.00 -30.03   74
 29  \w     43.00  92.00   0.50    0.06    --   85.25 -95.00  72.95   98
 30  \w    -97.00 -32.00   0.50    0.06    --  -78.00 114.00 -11.32  130
 31  \w   -125.00 -97.00   0.50    0.06    --  -79.50-113.00 -78.43   56
 32  \w   -126.00 -92.00   0.50    0.06    --  -79.50-123.00  53.21   68
 33  \w    -92.00 -51.00   0.50    0.06    --  -76.37 112.00 -60.00   82
 34  \w    -97.00 -32.00   0.50    0.06    --  -78.00 114.00  86.27  130
 35  \w   -130.00 -91.00   0.50    0.06    --  -79.50 -40.00 -48.32   78
 36  \w   -124.00 -87.00   0.50    0.06    --  -74.00 -44.00-132.64   74
 37  \w   -130.00 -91.00   0.50    0.06    --  -79.50 -40.00 -67.93   78
 38  \w   -131.00 -68.00   0.50    0.06    --  -79.50 -21.00  -4.17  126
 39  \w     40.00  90.00   0.50    0.06    --   82.26 -95.00 -90.00  100
 40  \w   -102.00 -67.00   0.50    0.06    --  -54.00 -51.00 -98.11   70
 41  \w     40.00  90.00   0.50    0.06    --   82.26 -95.00 -30.00  100
 42  \w     40.00  90.00   0.50    0.06    --   82.26 -95.00 150.00  100
 43  \w     42.00  93.00   0.50    0.06    --   85.25 -98.00-113.41  102
 44  \w   -129.00 -92.00   0.50    0.06    --  -79.50 -45.00 -19.45   74
 45  \w   -124.00 -95.00   0.50    0.06    --  -79.50 -65.00 107.36   58
 46  \w   -126.00 -92.00   0.50    0.06    --  -79.50-123.00-120.38   68
 47  \w     34.00  60.00   0.50    0.06    --   22.00  59.00 -39.95   52
 48  \w     59.00  94.00   0.50    0.06    --   46.00  52.00  -5.51   70
 49  \w     98.00 135.00   0.50    0.06    --   85.25  44.00-142.89   74
 50  \w   -102.00 -67.00   0.50    0.06    --  -54.00 -51.00-135.29   70
 51  \w    -92.00 -31.00   0.50    0.06    --  -76.37 112.00 120.00  122
 52  \w     56.00  91.00   0.50    0.06    --   42.00  50.00  45.50   70
 53  \w    -97.00 -32.00   0.50    0.06    --  -78.00 114.00 -98.77  130
 54  \w     34.00  60.00   0.50    0.06    --   22.00  59.00 151.47   52
 55  \w     34.00  60.00   0.50    0.06    --   22.00  57.00 119.84   52
 56  \w   -107.00 -72.00   0.50    0.06    --  -58.00 -48.00  37.70   70
 57  \w     40.00  90.00   0.50    0.06    --   82.26 -95.00   0.00  100
 58  \w   -126.00 -92.00   0.50    0.06    --  -79.50-122.00 167.98   68
 59  \w    -92.00 -31.00   0.50    0.06    --  -76.37 112.00  60.00  122
 60  \w   -125.00 -90.00   0.50    0.06    --  -79.50 -62.00  58.74   70
 61  \w   -126.00 -92.00   0.50    0.06    --  -79.50-122.00  14.54   68
 62  \w    -97.00 -32.00   0.50    0.06    --  -78.00 114.00 151.26  130
 63  \w   -125.00 -94.00   0.50    0.06    --  -79.50-119.00 -50.16   62
 64  \w    -91.00 -28.00   0.50    0.06    --  -74.00 109.00-142.65  126
 65  \w   -124.00 -95.00   0.50    0.06    --  -79.50 -65.00 -76.06   58
 66  \w   -126.00 -88.00   0.50    0.06    --  -79.50-131.00  95.03   76
 67  \w   -120.00 -86.00   0.50    0.06    --  -74.00 -59.00 111.15   68
 68  \w     99.00 135.00   0.50    0.06    --   85.25  46.00 165.15   72
 69  \w   -125.00 -91.00   0.50    0.06    --  -79.50 -60.00 -92.99   68
 70  \w   -126.00 -88.00   0.50    0.06    --  -79.50-131.00 145.77   76
;
_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      0.0476214000
_diffrn_orient_matrix_UB_12      0.0299220000
_diffrn_orient_matrix_UB_13      0.0492794000
_diffrn_orient_matrix_UB_21      -0.1198040000
_diffrn_orient_matrix_UB_22      0.0621740000
_diffrn_orient_matrix_UB_23      0.0401283000
_diffrn_orient_matrix_UB_31      -0.0012874000
_diffrn_orient_matrix_UB_32      -0.0960308000
_diffrn_orient_matrix_UB_33      0.0421331000
_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  0.0340
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            82398
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.269
_diffrn_reflns_theta_min         3.392
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.522
_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    1.142
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_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          0.320
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     874
_refine_ls_number_reflns         13958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0821P)^2^+1.1989P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11014
_reflns_number_total             13958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           6-Li_C6H6
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_database_code               1574519
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              74219
_shelx_hkl_checksum              19740