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_1574513
_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         'C20 H27 B N2 Si'
_chemical_formula_sum            'C20 H27 B N2 Si'
_chemical_formula_weight         334.33
_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             2025-01-22
_audit_creation_method           'CIF-fill 1.5q (K.Radacki, 2005-25)'
_audit_update_record
;
2025-02-20 deposited with the CCDC.	2025-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                83.564(3)
_cell_angle_beta                 85.956(2)
_cell_angle_gamma                83.743(2)
_cell_formula_units_Z            6
_cell_length_a                   6.7806(2)
_cell_length_b                   19.1991(7)
_cell_length_c                   22.5503(6)
_cell_measurement_reflns_used    16886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.6540
_cell_measurement_theta_min      3.1770
_cell_volume                     2894.70(16)
_computing_cell_refinement       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection
;
 CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))
;
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     46.00 110.00   0.50    1.44    --   58.84  20.00  81.00  128
  2  \w   -112.00 -48.00   0.50    1.44    --  -60.36 -20.00 -85.00  128
  3  \w   -121.00 -57.00   0.50    1.44    --  -69.98 -20.00 -85.00  128
  4  \w   -128.00 -64.00   0.50    1.44    --  -76.36 -20.00 -85.00  128
  5  \w     64.00 128.00   0.50    1.44    --   76.69  20.00  81.00  128
  6  \w     72.00 136.00   0.50    1.44    --   84.46  20.00  81.00  128
  7  \w     72.00 136.00   0.50    1.44    --   84.46  20.00  81.00  128
  8  \w    -87.00 -52.00   0.50    1.44    --  -38.00 -49.00-167.87   70
  9  \w    -99.00 -64.00   0.50    1.44    --  -50.00 -48.00-103.19   70
 10  \w   -107.00 -72.00   0.50    1.44    --  -58.00 -50.00 121.77   70
 11  \w     16.00  66.00   0.50    1.44    --   58.84 -95.00  90.00  100
 12  \w     16.00  66.00   0.50    1.44    --   58.84 -95.00 -60.00  100
 13  \w   -111.00 -76.00   0.50    1.44    --  -62.00 -50.00-161.56   70
 14  \w   -110.00 -75.00   0.50    1.44    --  -62.00 -52.00 -10.20   70
 15  \w   -117.00 -84.00   0.50    1.44    --  -70.00 -57.00-172.30   66
 16  \w     59.00 123.00   0.50    1.44    --   71.51  20.00  81.00  128
 17  \w   -120.00 -86.00   0.50    1.44    --  -74.00 -60.00  -2.74   68
 18  \w   -121.00 -86.00   0.50    1.44    --  -74.00 -57.00 171.74   70
 19  \w   -124.00 -86.00   0.50    1.44    --  -74.00 -42.00-108.92   76
 20  \w   -120.00 -86.00   0.50    1.44    --  -74.00 -59.00-155.09   68
 21  \w    -92.00 -31.00   0.50    1.44    --  -76.36 112.00  60.00  122
 22  \w    -92.00 -31.00   0.50    1.44    --  -76.36 112.00   0.00  122
 23  \w    -92.00 -31.00   0.50    1.44    --  -76.36 112.00-150.00  122
 24  \w     34.00  84.00   0.50    1.44    --   76.69 -95.00-180.00  100
 25  \w     31.00  93.00   0.50    1.44    --   76.69-112.00   0.00  124
 26  \w     31.00  93.00   0.50    1.44    --   76.69-112.00 -90.00  124
 27  \w   -128.00 -93.00   0.50    1.44    --  -79.50 -49.00 -85.00   70
 28  \w   -126.00 -92.00   0.50    1.44    --  -79.50-123.00  21.79   68
 29  \w   -128.00 -93.00   0.50    1.44    --  -79.50 -50.00 112.55   70
 30  \w   -124.00 -94.00   0.50    1.44    --  -79.50 -64.00  83.72   60
 31  \w    -97.00 -33.00   0.50    1.44    --  -79.50 116.00 114.42  128
 32  \w   -124.00 -94.00   0.50    1.44    --  -79.50 -64.00-149.77   60
 33  \w   -126.00 -92.00   0.50    1.44    --  -79.50-123.00-123.79   68
 34  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00 -90.00  100
 35  \w     48.00 135.00   0.50    1.44    --   84.46  15.00-180.00  174
 36  \w     48.00 135.00   0.50    1.44    --   84.46  15.00-180.00  174
 37  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00-180.00  100
 38  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00 120.00  100
 39  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00   0.00  100
 40  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00 150.00  100
 41  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00-120.00  100
 42  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00 -60.00  100
 43  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00-150.00  100
 44  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00  30.00  100
 45  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00  90.00  100
 46  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00 -30.00  100
 47  \w     42.00  92.00   0.50    1.44    --   84.46 -95.00  60.00  100
 48  \w    -21.00   6.00   0.50    1.44    --  -14.00  95.00-178.66   54
 49  \w     30.00  56.00   0.50    1.44    --   18.00  60.00 -34.20   52
 50  \w     30.00  56.00   0.50    1.44    --   18.00  60.00-169.71   52
 51  \w     34.00  60.00   0.50    1.44    --   22.00  59.00 -87.30   52
 52  \w     34.00  60.00   0.50    1.44    --   22.00  59.00 114.29   52
 53  \w    -79.00 -44.00   0.50    1.44    --  -30.00 -49.00 -10.87   70
 54  \w    -91.00 -56.00   0.50    1.44    --  -42.00 -48.00  39.88   70
 55  \w   -118.00 -83.00   0.50    1.44    --  -70.00 -51.00-125.27   70
 56  \w   -121.00 -86.00   0.50    1.44    --  -74.00 -58.00 -49.48   70
 57  \w   -127.00 -92.00   0.50    1.44    --  -79.50 -54.00  98.89   70
 58  \w   -130.00 -91.00   0.50    1.44    --  -79.50 -40.00  31.95   78
 59  \w   -126.00 -92.00   0.50    1.44    --  -79.50-123.00 -97.86   68
 60  \w   -126.00 -93.00   0.50    1.44    --  -79.50-121.00  49.55   66
 61  \w   -126.00 -92.00   0.50    1.44    --  -79.50-123.00 -61.50   68
;
_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      0.1158611000
_diffrn_orient_matrix_UB_12      -0.0309673000
_diffrn_orient_matrix_UB_13      0.0548939000
_diffrn_orient_matrix_UB_21      0.1974473000
_diffrn_orient_matrix_UB_22      0.0071409000
_diffrn_orient_matrix_UB_23      -0.0372783000
_diffrn_orient_matrix_UB_31      0.0037833000
_diffrn_orient_matrix_UB_32      0.0746940000
_diffrn_orient_matrix_UB_33      0.0184411000
_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  0.0616
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20540
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.166
_diffrn_reflns_theta_min         2.891
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_preparation
;
 Crystals were grown at RT from saturated solution in DCM. 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          0.052
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         20540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0960P)^2^+1.0655P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.1775
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15869
_reflns_number_total             20540
_reflns_threshold_expression     'I > 2\s(I)'
_twin_dimensionality             triperiodic
_twin_formation_mechanism        gt
_twin_morphology                 polysynthetic
_twin_special_details
;
 Component 2 rotated by -179.9696\% 
 around [-0.00 0.71 -0.71] (reciprocal) or [-0.11 0.80 -0.59] (direct)
;
_cod_data_source_file            d5sc01395j2.cif
_cod_data_source_block           6-TMS
_cod_depositor_comments
'Adding full bibliography for 1574505--1574520.cif.'
_cod_database_code               1574513
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.839
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              62851
_shelx_hkl_checksum              49376