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_1575383
_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         'C19 H39 B3 N6'
_chemical_formula_sum            'C19 H39 B3 N6'
_chemical_formula_weight         383.99
_chemical_name_systematic        4
_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             2023-03-17
_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_update_record
;
2025-07-01 deposited with the CCDC.	2025-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                81.038(2)
_cell_angle_beta                 80.620(2)
_cell_angle_gamma                78.599(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7226(2)
_cell_length_b                   10.6260(3)
_cell_length_c                   14.8988(3)
_cell_measurement_reflns_used    10725
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0940
_cell_measurement_theta_min      2.9830
_cell_volume                     1172.76(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 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     28.00  79.00   0.50    0.64    --   71.14 -95.00 120.00  102
  2  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00  30.00  100
  3  \w     28.00  79.00   0.50    0.64    --   71.14 -95.00 -60.00  102
  4  \w     16.00  66.00   0.50    0.64    --   58.28 -95.00-150.00  100
  5  \w     28.00  79.00   0.50    0.64    --   71.14 -95.00-180.00  102
  6  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00-180.00  100
  7  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00-150.00  100
  8  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00-120.00  100
  9  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00   0.00  100
 10  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00 -30.00  100
 11  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00  60.00  100
 12  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00  90.00  100
 13  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00 120.00  100
 14  \w     40.00  90.00   0.50    0.64    --   82.28 -95.00 150.00  100
 15  \w     43.00  91.00   0.50    0.64    --   85.25 -93.00 -82.01   96
 16  \w     51.00 135.00   0.50    0.64    --   85.25  13.00  61.55  168
 17  \w    101.00 132.00   0.50    0.64    --   85.25  49.00  56.62   62
 18  \w     55.00  90.00   0.50    0.64    --   42.00  52.00  94.22   70
 19  \w     44.00  79.00   0.50    0.64    --   30.00  49.00 -50.36   70
 20  \w     76.00 116.00   0.50    0.64    --   64.71  38.00 -28.98   80
 21  \w    101.00 134.00   0.50    0.64    --   85.25  45.00 -91.46   66
 22  \w     70.00 134.00   0.50    0.64    --   82.28  21.00-118.00  128
 23  \w     59.00 123.00   0.50    0.64    --   71.14  21.00-118.00  128
 24  \w     46.00 110.00   0.50    0.64    --   58.28  21.00-118.00  128
 25  \w    -92.00 -31.00   0.50    0.64    --  -76.35 112.00-150.00  122
 26  \w    -98.00 -32.00   0.50    0.64    --  -78.00 118.00 -28.75  132
 27  \w    -97.00 -32.00   0.50    0.64    --  -78.00 114.00  12.36  130
 28  \w    -97.00 -32.00   0.50    0.64    --  -78.00 114.00  73.15  130
 29  \w   -102.00 -32.00   0.50    0.64    --  -79.50 130.00  52.28  140
 30  \w    -97.00 -32.00   0.50    0.64    --  -78.00 114.00  88.67  130
 31  \w   -128.00 -65.00   0.50    0.64    --  -76.35 -21.00  74.00  126
 32  \w   -124.00 -92.00   0.50    0.64    --  -79.50 -63.00 147.07   64
 33  \w   -124.00 -95.00   0.50    0.64    --  -79.50 -65.00  24.38   58
 34  \w   -124.00 -89.00   0.50    0.64    --  -78.00 -60.00 -80.92   70
 35  \w   -126.00 -92.00   0.50    0.64    --  -79.50 -57.00-140.66   68
 36  \w   -127.00 -92.00   0.50    0.64    --  -79.50 -53.00 -98.98   70
 37  \w   -128.00 -93.00   0.50    0.64    --  -79.50 -52.00 -64.99   70
 38  \w   -128.00 -93.00   0.50    0.64    --  -79.50 -51.00 -31.06   70
 39  \w   -107.00 -72.00   0.50    0.64    --  -58.00 -48.00 -33.76   70
 40  \w   -130.00 -91.00   0.50    0.64    --  -79.50 -39.00 -46.51   78
 41  \w   -130.00 -92.00   0.50    0.64    --  -79.50 -43.00  60.06   76
 42  \w   -121.00 -58.00   0.50    0.64    --  -69.45 -21.00  74.00  126
 43  \w   -112.00 -48.00   0.50    0.64    --  -59.96 -21.00  74.00  128
 44  \w   -106.00 -71.00   0.50    0.64    --  -58.00 -52.00 158.28   70
 45  \w   -128.00 -93.00   0.50    0.64    --  -79.50 -52.00 147.73   70
 46  \w   -126.00 -86.00   0.50    0.64    --  -79.50-134.00 115.82   80
 47  \w   -127.00 -90.00   0.50    0.64    --  -79.50-126.00 176.85   74
 48  \w   -126.00 -91.00   0.50    0.64    --  -79.50-124.00 145.96   70
 49  \w   -126.00 -93.00   0.50    0.64    --  -79.50-120.00  48.27   66
 50  \w   -126.00 -93.00   0.50    0.64    --  -79.50-120.00 -96.82   66
;
_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      0.1012135000
_diffrn_orient_matrix_UB_12      -0.1373012000
_diffrn_orient_matrix_UB_13      0.0273499000
_diffrn_orient_matrix_UB_21      0.1747759000
_diffrn_orient_matrix_UB_22      0.0534593000
_diffrn_orient_matrix_UB_23      -0.0109985000
_diffrn_orient_matrix_UB_31      -0.0375412000
_diffrn_orient_matrix_UB_32      0.0229629000
_diffrn_orient_matrix_UB_33      0.1014741000
_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  0.0361
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22823
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.050
_diffrn_reflns_theta_min         3.031
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.826
_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            'clear colourless'
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_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_recrystallization_method
'Re-crystallisation from solvent: pentane'
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0794P)^2^+0.1769P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3765
_reflns_number_total             4417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03752b2.cif
_cod_data_source_block           NiHe002_NiHe_a
_cod_depositor_comments
'Adding full bibliography for 1575379--1575386.cif.'
_cod_database_code               1575383
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              1506