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_1575382
_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         'C21 H45 B4 N7'
_chemical_formula_sum            'C21 H45 B4 N7'
_chemical_formula_weight         438.88
_chemical_name_systematic        5
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 90.6180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5939(2)
_cell_length_b                   16.5266(2)
_cell_length_c                   11.71550(10)
_cell_measurement_reflns_used    16874
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.7000
_cell_measurement_theta_min      5.3410
_cell_volume                     2631.86(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     37.00  93.00   0.50    0.18    --   82.28-112.00-150.00  112
  2  \w     37.00  93.00   0.50    0.18    --   82.28-112.00 -60.00  112
  3  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00 -60.00  100
  4  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00-150.00  100
  5  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00 -90.00  100
  6  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00-120.00  100
  7  \w     29.00  79.00   0.50    0.18    --   71.34 -95.00-120.00  100
  8  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00   0.00  100
  9  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00  60.00  100
 10  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00 120.00  100
 11  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00 -30.00  100
 12  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00  30.00  100
 13  \w     40.00  90.00   0.50    0.18    --   82.28 -95.00-180.00  100
 14  \w    103.00 131.00   0.50    0.18    --   85.25 114.00 113.82   56
 15  \w     93.00 132.00   0.50    0.18    --   85.25 132.00 -36.71   78
 16  \w     98.00 133.00   0.50    0.18    --   85.25  54.00 -60.82   70
 17  \w     98.00 136.00   0.50    0.18    --   85.25  43.00-122.04   76
 18  \w     46.00 133.00   0.50    0.18    --   82.28  15.00  60.00  174
 19  \w     96.00 137.00   0.50    0.18    --   85.25  35.00 149.31   82
 20  \w     46.00 133.00   0.50    0.18    --   82.28  15.00 150.00  174
 21  \w    -88.00 -51.00   0.50    0.18    --  -38.00 -44.00 175.05   74
 22  \w    -74.00 -39.00   0.50    0.18    --  -26.00 -52.00 -53.95   70
 23  \w    -98.00 -63.00   0.50    0.18    --  -50.00 -51.00-107.63   70
 24  \w    -54.00 -26.00   0.50    0.18    --  -14.00 -59.00-112.23   56
 25  \w    -54.00 -26.00   0.50    0.18    --  -14.00 -55.00  42.53   56
 26  \w   -130.00 -92.00   0.50    0.18    --  -79.50 -42.00 176.73   76
 27  \w   -123.00 -97.00   0.50    0.18    --  -79.50 -66.00 154.82   52
 28  \w   -122.00 -87.00   0.50    0.18    --  -74.00 -53.00 100.61   70
 29  \w   -124.00 -89.00   0.50    0.18    --  -78.00 -60.00  62.50   70
 30  \w   -126.00 -92.00   0.50    0.18    --  -79.50 -57.00  59.38   68
 31  \w   -103.00 -68.00   0.50    0.18    --  -54.00 -50.00 162.37   70
 32  \w   -110.00 -75.00   0.50    0.18    --  -62.00 -52.00  11.96   70
 33  \w   -106.00 -71.00   0.50    0.18    --  -58.00 -51.00  39.01   70
 34  \w   -128.00 -93.00   0.50    0.18    --  -79.50 -49.00  17.66   70
 35  \w   -107.00 -72.00   0.50    0.18    --  -58.00 -47.00 -54.43   70
 36  \w   -125.00 -91.00   0.50    0.18    --  -79.50 -60.00-117.69   68
 37  \w   -129.00 -93.00   0.50    0.18    --  -79.50 -47.00-150.93   72
 38  \w   -129.00 -93.00   0.50    0.18    --  -79.50 -48.00-103.17   72
 39  \w   -130.00 -92.00   0.50    0.18    --  -79.50 -43.00 -58.15   76
 40  \w   -126.00 -96.00   0.50    0.18    --  -79.50-116.00  21.02   60
 41  \w   -126.00 -87.00   0.50    0.18    --  -79.50-133.00 -42.34   78
 42  \w   -126.00 -84.00   0.50    0.18    --  -79.50-138.00 100.69   84
 43  \w   -126.00 -93.00   0.50    0.18    --  -79.50-120.00 134.81   66
 44  \w   -101.00 -31.00   0.50    0.18    --  -78.00 128.00-128.90  140
 45  \w   -100.00 -33.00   0.50    0.18    --  -79.50 123.00 -55.59  134
 46  \w    -97.00 -33.00   0.50    0.18    --  -79.50 116.00  21.35  128
 47  \w    -97.00 -33.00   0.50    0.18    --  -79.50 116.00  64.32  128
 48  \w    -99.00 -32.00   0.50    0.18    --  -79.50 122.00 118.17  134
 49  \w    -97.00 -33.00   0.50    0.18    --  -79.50 117.00 103.31  128
 50  \w    -88.00 -14.00   0.50    0.18    --  -60.16 126.00  60.00  148
 51  \w    -92.00 -31.00   0.50    0.18    --  -76.35 112.00 -60.00  122
;
_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      -0.0630359000
_diffrn_orient_matrix_UB_12      -0.0742672000
_diffrn_orient_matrix_UB_13      -0.0318910000
_diffrn_orient_matrix_UB_21      0.0599653000
_diffrn_orient_matrix_UB_22      -0.0111326000
_diffrn_orient_matrix_UB_23      -0.1097591000
_diffrn_orient_matrix_UB_31      0.0726779000
_diffrn_orient_matrix_UB_32      -0.0551929000
_diffrn_orient_matrix_UB_33      0.0650177000
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24715
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         4.211
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023) 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    1.108
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_preparation
;
 Crystals were grown from saturated solution of pentane 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          0.280
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0526P)^2^+1.8380P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2268
_reflns_number_total             2405
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03752b2.cif
_cod_data_source_block           NiHe003_NiHe_a
_cod_depositor_comments
'Adding full bibliography for 1575379--1575386.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1575382
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.873
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              5528