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_1574506
_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         'C12 H15 B N2 O3'
_chemical_formula_sum            'C12 H15 B N2 O3'
_chemical_formula_weight         246.07
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-05-09
_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                 103.002(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7968(3)
_cell_length_b                   5.9025(2)
_cell_length_c                   17.2316(4)
_cell_measurement_reflns_used    6145
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.8930
_cell_measurement_theta_min      3.8870
_cell_volume                     1268.19(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     60.00  91.00   0.50    0.06    --   52.00  69.00 103.14   62
  2  \w     65.00  97.00   0.50    0.06    --   56.00  62.00  77.57   64
  3  \w     73.00 104.00   0.50    0.06    --   68.00  75.00  60.43   62
  4  \w     87.00 115.00   0.50    0.26    --   76.07  64.00 -43.64   56
  5  \w     55.00 106.00   0.50    0.06    --   71.48 164.00 -68.00  102
  6  \w     55.00 112.00   0.50    0.26    --   76.87 164.00 -68.00  114
  7  \w     37.00 106.00   0.50    0.26    --   76.87-126.00-180.00  138
  8  \w     39.00 111.00   0.50    0.06    --   65.37-164.00 -92.00  144
  9  \w     33.00 102.00   0.50    0.26    --   76.87-118.00  56.00  138
 10  \w     28.00  96.00   0.50    0.06    --   71.48-118.00  56.00  136
 11  \w     22.00  90.00   0.50    0.06    --   65.37-118.00  56.00  136
 12  \w     34.00  80.00   0.50    0.06    --   71.48 -95.00  60.00   92
 13  \w   -105.00 -57.00   0.50    0.26    --  -75.71 126.00  60.00   96
 14  \w   -101.00 -32.00   0.50    0.26    --  -75.71 118.00 142.00  138
 15  \w    -98.00 -30.00   0.50    0.06    --  -73.64 118.00 142.00  136
 16  \w   -108.00 -48.00   0.50    0.06    --  -73.64-164.00 -92.00  120
 17  \w   -100.00 -48.00   0.50    0.06    --  -65.03-164.00 -92.00  104
 18  \w   -122.00 -97.00   0.50    0.26    --  -77.32 -38.00 -33.47   50
 19  \w   -121.00 -96.00   0.50    0.26    --  -77.32 -54.00-140.76   50
 20  \w   -123.00 -90.00   0.50    0.26    --  -77.32 -42.00-102.04   66
 21  \w   -118.00 -85.00   0.50    0.06    --  -72.00 -40.00 -73.05   66
 22  \w    -92.00 -61.00   0.50    0.06    --  -52.00 -64.00 -33.61   62
 23  \w   -118.00 -85.00   0.50    0.06    --  -72.00 -40.00-144.16   66
 24  \w   -118.00 -93.00   0.50    0.26    --  -77.32 -41.00  78.92   50
 25  \w   -104.00 -72.00   0.50    0.06    --  -68.00 -75.00 136.32   64
 26  \w    -76.00 -45.00   0.50    0.06    --  -40.00 -74.00 105.33   62
;
_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      -0.0113248000
_diffrn_orient_matrix_UB_12      0.0425118000
_diffrn_orient_matrix_UB_13      -0.0897655000
_diffrn_orient_matrix_UB_21      -0.0191343000
_diffrn_orient_matrix_UB_22      -0.2549799000
_diffrn_orient_matrix_UB_23      -0.0164049000
_diffrn_orient_matrix_UB_31      -0.1214785000
_diffrn_orient_matrix_UB_32      0.0362851000
_diffrn_orient_matrix_UB_33      -0.0101779000
_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  0.0365
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12496
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.941
_diffrn_reflns_theta_min         3.912
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.727
_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 pale colourless'
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_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          0.300
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0607P)^2^+0.2509P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2075
_reflns_number_total             2470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           1-Boc
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1574506
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.806
_shelx_estimated_absorpt_t_max   0.915
_shelx_res_checksum              40103
_shelx_hkl_checksum              2741