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_1574509
_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         'C7 H7 B N2 O'
_chemical_formula_sum            'C7 H7 B N2 O'
_chemical_formula_weight         145.96
_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             2023-05-08
_audit_creation_method           'CIF-fill 1.4c (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                 96.378(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6003(2)
_cell_length_b                   7.2677(2)
_cell_length_c                   12.3523(3)
_cell_measurement_reflns_used    3928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9380
_cell_measurement_theta_min      5.8480
_cell_volume                     678.08(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (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 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 0.957
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     14.00  76.00   0.50    0.05    --   58.90-109.00 134.00  124
  2  \w     31.00  93.00   0.50    0.10    --   76.61-112.00-150.00  124
  3  \w     42.00  92.00   0.50    0.10    --   84.39 -95.00-150.00  100
  4  \w     42.00  92.00   0.50    0.10    --   84.39 -95.00 -30.00  100
  5  \w     26.00  88.00   0.50    0.05    --   71.47-109.00 134.00  124
  6  \w     31.00  92.00   0.50    0.10    --   76.61-109.00 134.00  122
  7  \w     42.00  92.00   0.50    0.10    --   84.39 -95.00 150.00  100
  8  \w     48.00 135.00   0.50    0.10    --   84.39  15.00 -90.00  174
  9  \w    -98.00 -23.00   0.50    0.05    --  -70.16 126.00   0.00  150
 10  \w    -98.00 -23.00   0.50    0.05    --  -70.16 126.00 -60.00  150
 11  \w    -77.00 -15.00   0.50    0.05    --  -60.45 109.00-129.00  124
 12  \w    -92.00 -31.00   0.50    0.10    --  -76.30 109.00-129.00  122
 13  \w    -87.00 -25.00   0.50    0.05    --  -70.16 109.00-129.00  124
 14  \w     -5.00  21.00   0.50    0.05    --  -10.00  77.00  87.43   52
 15  \w    -96.00 -58.00   0.50    0.05    --  -46.00 -43.00 173.90   76
 16  \w   -120.00 -86.00   0.50    0.10    --  -74.00 -59.00 169.24   68
 17  \w   -106.00 -71.00   0.50    0.05    --  -58.00 -51.00 133.14   70
 18  \w   -129.00 -93.00   0.50    0.10    --  -79.50 -48.00 123.74   72
 19  \w   -129.00 -93.00   0.50    0.10    --  -79.50 -47.00  55.93   72
 20  \w   -119.00 -84.00   0.50    0.05    --  -70.00 -47.00  76.96   70
 21  \w   -127.00 -92.00   0.50    0.10    --  -79.50 -54.00  22.94   70
 22  \w    -91.00 -55.00   0.50    0.05    --  -42.00 -46.00  10.85   72
 23  \w   -116.00 -79.00   0.50    0.05    --  -66.00 -45.00 -38.53   74
 24  \w   -120.00 -83.00   0.50    0.05    --  -70.00 -46.00 -61.49   74
 25  \w   -125.00 -91.00   0.50    0.10    --  -79.50 -60.00 -85.33   68
 26  \w   -126.00 -91.00   0.50    0.10    --  -79.50 -59.00-129.88   70
;
_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      -0.0221812000
_diffrn_orient_matrix_UB_12      0.2063442000
_diffrn_orient_matrix_UB_13      -0.0267940000
_diffrn_orient_matrix_UB_21      -0.1576541000
_diffrn_orient_matrix_UB_22      0.0096157000
_diffrn_orient_matrix_UB_23      0.0681107000
_diffrn_orient_matrix_UB_31      0.1274169000
_diffrn_orient_matrix_UB_32      0.0476278000
_diffrn_orient_matrix_UB_33      0.1019680000
_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  0.0262
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6554
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.594
_diffrn_reflns_theta_min         5.858
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.41.112a (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 light colourless'
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_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          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0548P)^2^+0.2056P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1149
_reflns_number_total             1328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           1-H
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574509
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.898
_shelx_estimated_absorpt_t_max   0.955
_shelx_res_checksum              87710
_shelx_hkl_checksum              17232