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_1574505
_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         'C10 H15 B N2 O Si'
_chemical_formula_sum            'C10 H15 B N2 O Si'
_chemical_formula_weight         218.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-09-29
_audit_creation_method           'CIF-fill 1.4m (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                   8.23510(10)
_cell_length_b                   12.22030(10)
_cell_length_c                   24.1907(2)
_cell_measurement_reflns_used    33748
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.9330
_cell_measurement_theta_min      3.6570
_cell_volume                     2434.44(4)
_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 0.992
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w   -125.00 -91.00   0.50    0.07    --  -79.50 -60.00  69.52   68
  2  \w   -124.00 -95.00   0.50    0.07    --  -79.50 -65.00   5.02   58
  3  \w   -118.00 -92.00   0.50    0.07    --  -79.50 -63.00 -44.12   52
  4  \w   -121.00 -86.00   0.50    0.07    --  -74.00 -56.00-121.59   70
  5  \w   -121.00 -86.00   0.50    0.07    --  -74.00 -58.00 -57.54   70
  6  \w   -111.00 -76.00   0.50    0.05    --  -62.00 -50.00-154.56   70
  7  \w   -126.00-100.00   0.50    0.07    --  -79.50 -52.00 -30.45   52
  8  \w   -117.00 -83.00   0.50    0.05    --  -70.00 -55.00 -15.62   68
  9  \w   -106.00 -71.00   0.50    0.05    --  -58.00 -51.00  36.48   70
 10  \w   -125.00 -96.00   0.50    0.07    --  -79.50 -49.00 146.78   58
 11  \w   -107.00 -72.00   0.50    0.05    --  -58.00 -48.00 129.00   70
 12  \w   -130.00 -91.00   0.50    0.07    --  -79.50 -41.00 114.12   78
 13  \w   -103.00 -68.00   0.50    0.05    --  -54.00 -49.00 112.05   70
 14  \w   -125.00 -86.00   0.50    0.07    --  -74.00 -40.00-176.61   78
 15  \w   -131.00-104.00   0.50    0.07    --  -79.50 -35.00 -85.22   54
 16  \w   -130.00 -92.00   0.50    0.07    --  -79.50 -42.00  -3.00   76
 17  \w    -92.00 -54.00   0.50    0.05    --  -42.00 -43.00 -26.08   76
 18  \w    -95.00 -60.00   0.50    0.05    --  -46.00 -47.00 -64.55   70
 19  \w    -92.00 -35.00   0.50    0.07    --  -79.50 102.00-128.77  114
 20  \w   -100.00 -29.00   0.50    0.07    --  -76.35 126.00  41.00  142
 21  \w   -108.00 -33.00   0.50    0.07    --  -79.50 139.00  43.18  150
 22  \w   -100.00 -33.00   0.50    0.07    --  -79.50 123.00 -14.65  134
 23  \w    -88.00 -14.00   0.50    0.05    --  -60.16 126.00  41.00  148
 24  \w    -97.00 -22.00   0.50    0.05    --  -69.76 126.00  41.00  150
 25  \w    -75.00 -37.00   0.50    0.07    --  -79.50 140.00 162.87   76
 26  \w    -97.00 -36.00   0.50    0.07    --  -79.50 119.00 141.35  122
 27  \w    -97.00 -32.00   0.50    0.07    --  -78.00 114.00  68.89  130
 28  \w    -97.00 -32.00   0.50    0.07    --  -78.00 114.00 -37.44  130
 29  \w   -125.00-100.00   0.50    0.07    --  -79.50-111.00-101.91   50
 30  \w   -126.00 -93.00   0.50    0.07    --  -79.50-120.00 -79.89   66
 31  \w   -126.00 -95.00   0.50    0.07    --  -79.50-117.00 -62.14   62
 32  \w     45.00  93.00   0.50    0.07    --   85.25 -97.00-134.40   96
 33  \w     20.00  86.00   0.50    0.05    --   58.57-126.00 -34.00  132
 34  \w     24.00  99.00   0.50    0.05    --   71.34-126.00 -34.00  150
 35  \w     67.00  92.00   0.50    0.07    --   85.25 -96.00 -85.19   50
 36  \w     44.00  91.00   0.50    0.07    --   85.25 -96.00-105.02   94
 37  \w     35.00 101.00   0.50    0.07    --   82.28-126.00 -34.00  132
 38  \w     41.00  90.00   0.50    0.07    --   82.28 -95.00 -30.00   98
 39  \w     47.00  89.00   0.50    0.07    --   82.28 -95.00  30.00   84
 40  \w     46.00  89.00   0.50    0.07    --   82.28 -95.00   0.00   86
 41  \w     16.00  66.00   0.50    0.05    --   58.57 -95.00 -60.00  100
 42  \w     56.00  90.00   0.50    0.07    --   82.28 -95.00  60.00   68
 43  \w     40.00  90.00   0.50    0.07    --   82.28 -95.00  90.00  100
 44  \w     48.00  87.00   0.50    0.07    --   82.28 -95.00 120.00   78
 45  \w     44.00  92.00   0.50    0.07    --   85.25 -99.00 174.69   96
 46  \w     42.00  93.00   0.50    0.07    --   85.25 -97.00 138.58  102
 47  \w     60.00  88.00   0.50    0.07    --   82.28 -95.00 -60.00   56
 48  \w     56.00  92.00   0.50    0.07    --   85.25 -95.00-161.43   72
 49  \w     84.00 131.00   0.50    0.07    --   85.25  12.00   1.20   94
 50  \w    107.00 134.00   0.50    0.07    --   85.25  44.00  90.25   54
 51  \w    105.00 131.00   0.50    0.07    --   85.25  48.00 144.85   52
 52  \w     97.00 123.00   0.50    0.07    --   85.25  59.00  47.13   52
 53  \w     93.00 132.00   0.50    0.07    --   85.25  27.00-139.22   78
 54  \w     99.00 125.00   0.50    0.07    --   85.25 123.00 -65.23   52
 55  \w     96.00 132.00   0.50    0.07    --   85.25 129.00   8.13   72
 56  \w    105.00 131.00   0.50    0.07    --   85.25 125.00 147.82   52
;
_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      0.0000122000
_diffrn_orient_matrix_UB_12      0.0116397000
_diffrn_orient_matrix_UB_13      -0.0634407000
_diffrn_orient_matrix_UB_21      -0.1417597000
_diffrn_orient_matrix_UB_22      -0.0818537000
_diffrn_orient_matrix_UB_23      -0.0038794000
_diffrn_orient_matrix_UB_31      -0.1220260000
_diffrn_orient_matrix_UB_32      0.0951009000
_diffrn_orient_matrix_UB_33      0.0045105000
_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  0.0232
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            45706
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.958
_diffrn_reflns_theta_min         3.654
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    1.502
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.621
_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            'clear colourless'
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_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          0.240
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+1.0603P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2416
_reflns_number_total             2489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           2-H
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_database_code               1574505
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.714
_shelx_estimated_absorpt_t_max   0.864
_shelx_res_checksum              80097
_shelx_hkl_checksum              37888