Atom-efficient synthesis of BN-heterocycles from oligoboranes and isonitriles.
Hensiek, Nicola; Duwe, Dario; Arrowsmith, Merle; Michel, Maximilian; Braunschweig, Holger; Chemical communications (Cambridge, England) 61 (2025) 14721–14724; doi:10.1039/d5cc03752b

data_1575385
_publ_section_title
;
 Atom-efficient synthesis of BN-heterocycles from oligoboranes and
 isonitriles.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14721
_journal_page_last               14724
_journal_paper_doi               10.1039/d5cc03752b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C26 H50 B3 N7'
_chemical_formula_sum            'C26 H50 B3 N7'
_chemical_formula_weight         493.16
_chemical_name_systematic        3-Cy
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_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             2023-03-22
_audit_creation_method           'CIF-fill 1.3t (K.Radacki, 2005-23)'
_audit_update_record
;
2025-07-01 deposited with the CCDC.	2025-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                89.1930(10)
_cell_angle_beta                 72.7140(10)
_cell_angle_gamma                65.3450(10)
_cell_formula_units_Z            2
_cell_length_a                   10.7176(2)
_cell_length_b                   11.7085(2)
_cell_length_c                   13.7152(2)
_cell_measurement_reflns_used    19519
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.8050
_cell_measurement_theta_min      3.4040
_cell_volume                     1481.51(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w   -101.00 -32.00   0.50    0.09    --  -79.50 128.00-132.87  138
  2  \w    -98.00 -32.00   0.50    0.09    --  -79.50 120.00-161.74  132
  3  \w    -98.00 -32.00   0.50    0.09    --  -78.00 118.00 -28.10  132
  4  \w    -92.00 -31.00   0.50    0.09    --  -76.35 112.00-150.00  122
  5  \w    -97.00 -33.00   0.50    0.09    --  -79.50 116.00   3.67  128
  6  \w    -82.00 -34.00   0.50    0.09    --  -76.35  92.00  97.00   96
  7  \w    -65.00 -18.00   0.50    0.09    --  -60.16  92.00  97.00   94
  8  \w    -75.00 -28.00   0.50    0.09    --  -69.76  92.00  97.00   94
  9  \w   -102.00 -32.00   0.50    0.09    --  -79.50 129.00 155.58  140
 10  \w    -92.00 -35.00   0.50    0.09    --  -79.50 103.00  99.56  114
 11  \w   -125.00 -91.00   0.50    0.09    --  -79.50 -60.00 138.12   68
 12  \w   -127.00 -92.00   0.50    0.09    --  -79.50 -53.00 167.17   70
 13  \w   -117.00 -83.00   0.50    0.09    --  -70.00 -55.00  67.59   68
 14  \w   -128.00 -93.00   0.50    0.09    --  -79.50 -51.00  57.91   70
 15  \w   -121.00 -86.00   0.50    0.09    --  -74.00 -55.00  33.25   70
 16  \w   -128.00 -93.00   0.50    0.09    --  -79.50 -49.00  43.43   70
 17  \w   -128.00 -93.00   0.50    0.09    --  -79.50 -52.00  21.43   70
 18  \w   -128.00 -93.00   0.50    0.09    --  -79.50 -49.00 -65.56   70
 19  \w   -128.00 -93.00   0.50    0.09    --  -79.50 -49.00-148.45   70
 20  \w   -121.00 -81.00   0.50    0.09    --  -70.00 -37.00-102.00   80
 21  \w   -125.00 -85.00   0.50    0.09    --  -74.00 -37.00 -53.58   80
 22  \w   -127.00 -92.00   0.50    0.09    --  -79.50 -55.00 -23.68   70
 23  \w   -129.00 -93.00   0.50    0.09    --  -79.50 -46.00  81.63   72
 24  \w   -107.00 -72.00   0.50    0.09    --  -58.00 -47.00 172.65   70
 25  \w   -126.00 -91.00   0.50    0.09    --  -79.50-124.00 123.52   70
 26  \w   -126.00 -92.00   0.50    0.09    --  -79.50-123.00  82.26   68
 27  \w   -126.00 -93.00   0.50    0.09    --  -79.50-121.00 -32.36   66
 28  \w   -126.00 -93.00   0.50    0.09    --  -79.50-120.00-155.03   66
 29  \w   -126.00 -93.00   0.50    0.09    --  -79.50-120.00  -9.88   66
 30  \w    -95.00 -60.00   0.50    0.09    --  -46.00 -48.00 114.72   70
 31  \w    -87.00 -52.00   0.50    0.09    --  -38.00 -49.00 175.02   70
 32  \w    -91.00 -56.00   0.50    0.09    --  -42.00 -48.00  70.02   70
 33  \w    -87.00 -52.00   0.50    0.09    --  -38.00 -49.00 -40.11   70
 34  \w    -95.00 -60.00   0.50    0.09    --  -46.00 -49.00-137.20   70
 35  \w     17.00  64.00   0.50    0.09    --   58.57 -92.00 -14.00   94
 36  \w     40.00  90.00   0.50    0.09    --   82.28 -95.00  60.00  100
 37  \w     42.00  93.00   0.50    0.09    --   85.25 -98.00 -42.38  102
 38  \w     40.00  90.00   0.50    0.09    --   82.28 -95.00-180.00  100
 39  \w     40.00  90.00   0.50    0.09    --   82.28 -95.00-120.00  100
 40  \w     40.00  90.00   0.50    0.09    --   82.28 -95.00 -90.00  100
 41  \w     40.00  90.00   0.50    0.09    --   82.28 -95.00  30.00  100
 42  \w     40.00  90.00   0.50    0.09    --   82.28 -95.00 120.00  100
 43  \w     40.00  90.00   0.50    0.09    --   82.28 -95.00 150.00  100
 44  \w     40.00  90.00   0.50    0.09    --   82.28 -95.00  90.00  100
 45  \w     30.00  77.00   0.50    0.09    --   71.34 -92.00 -14.00   94
 46  \w     41.00  88.00   0.50    0.09    --   82.28 -92.00 -14.00   94
 47  \w     40.00  90.00   0.50    0.09    --   82.28 -95.00-150.00  100
 48  \w     46.00 133.00   0.50    0.09    --   82.28  15.00 -90.00  174
 49  \w     99.00 135.00   0.50    0.09    --   85.25  48.00 -72.91   72
 50  \w     91.00 132.00   0.50    0.09    --   85.25 138.00-107.99   82
 51  \w     71.00 137.00   0.50    0.09    --   85.25  19.00  28.96  132
 52  \w     98.00 133.00   0.50    0.09    --   85.25  54.00 162.88   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      0.0755282000
_diffrn_orient_matrix_UB_12      -0.0459321000
_diffrn_orient_matrix_UB_13      0.0820861000
_diffrn_orient_matrix_UB_21      -0.1372762000
_diffrn_orient_matrix_UB_22      -0.0066478000
_diffrn_orient_matrix_UB_23      0.0718364000
_diffrn_orient_matrix_UB_31      0.0576982000
_diffrn_orient_matrix_UB_32      -0.1383730000
_diffrn_orient_matrix_UB_33      -0.0465363000
_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  0.0240
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28558
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         3.402
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022) 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    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_preparation
;
 Crystals were grown from saturated solution of hexane at -30?C \%C. 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_recrystallization_method
'Re-crystallisation from solvent: pentane'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5386
_refine_ls_number_restraints     247
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0582P)^2^+0.2951P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4749
_reflns_number_total             5386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03752b2.cif
_cod_data_source_block           NiHe001_NiHe_a
_cod_depositor_comments
'Adding full bibliography for 1575379--1575386.cif.'
_cod_database_code               1575385
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              57809