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_1574507
_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         'C18 H21 B N2'
_chemical_formula_sum            'C18 H21 B N2'
_chemical_formula_weight         276.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-12-11
_audit_creation_method           'CIF-fill 1.5n (K.Radacki, 2005-24)'
_audit_update_record
;
2025-02-20 deposited with the CCDC.	2025-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.531(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3573(2)
_cell_length_b                   10.3560(3)
_cell_length_c                   17.9111(5)
_cell_measurement_reflns_used    7514
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0930
_cell_measurement_theta_min      4.8540
_cell_volume                     1545.33(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection
;
 CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))
;
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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 0.956
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     83.00 129.00   0.50    0.14    --   77.02  27.00-147.00   92
  2  \w     91.00 137.00   0.50    0.14    --   84.75  27.00-147.00   92
  3  \w     65.00 111.00   0.50    0.14    --   58.56  27.00-147.00   92
  4  \w     16.00  66.00   0.50    0.14    --   58.56 -95.00 150.00  100
  5  \w     42.00  92.00   0.50    0.14    --   84.75 -95.00-180.00  100
  6  \w     42.00  92.00   0.50    0.14    --   84.75 -95.00  60.00  100
  7  \w     29.00  79.00   0.50    0.14    --   71.28 -95.00  30.00  100
  8  \w   -129.00 -83.00   0.50    0.14    --  -76.40 -27.00  50.00   92
  9  \w     38.00 109.00   0.50    0.14    --   58.56  15.00  60.00  142
 10  \w     49.00 135.00   0.50    0.14    --   84.75  15.00 -60.00  172
 11  \w     16.00  51.00   0.50    0.14    --   58.56 -95.00 -90.00   70
 12  \w     39.00  93.00   0.50    0.14    --   84.75-112.00-180.00  108
 13  \w    -92.00 -31.00   0.50    0.14    --  -76.40 112.00  90.00  122
 14  \w     16.00  66.00   0.50    0.14    --   58.56 -95.00  60.00  100
 15  \w   -113.00 -67.00   0.50    0.14    --  -60.21 -27.00  50.00   92
 16  \w   -120.00 -34.00   0.50    0.14    --  -69.63 -15.00  90.00  172
 17  \w    -92.00 -31.00   0.50    0.14    --  -76.40 112.00   0.00  122
 18  \w   -122.00 -76.00   0.50    0.14    --  -69.63 -27.00  50.00   92
 19  \w     42.00  92.00   0.50    0.14    --   84.75 -95.00 -30.00  100
 20  \w   -127.00 -41.00   0.50    0.14    --  -76.40 -15.00 -30.00  172
 21  \w     34.00  85.00   0.50    0.14    --   77.02 -95.00 -60.00  102
 22  \w     34.00  85.00   0.50    0.14    --   77.02 -95.00 120.00  102
 23  \w     34.00  85.00   0.50    0.14    --   77.02 -95.00-150.00  102
;
_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      0.1662813000
_diffrn_orient_matrix_UB_12      0.0356487000
_diffrn_orient_matrix_UB_13      0.0376074000
_diffrn_orient_matrix_UB_21      0.0782799000
_diffrn_orient_matrix_UB_22      -0.0400039000
_diffrn_orient_matrix_UB_23      -0.0715048000
_diffrn_orient_matrix_UB_31      -0.0201437000
_diffrn_orient_matrix_UB_32      0.1388403000
_diffrn_orient_matrix_UB_33      -0.0302290000
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15652
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.272
_diffrn_reflns_theta_min         4.937
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024) 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    1.187
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_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          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0582
_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^)+(0.0949P)^2^+0.3597P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.1731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2425
_reflns_number_total             3056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           6-Me
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1574507
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              19445
_shelx_hkl_checksum              19749