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_1575386
_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_absolute_configuration unk
_chemical_formula_moiety         'C28 H48 B3 N7'
_chemical_formula_sum            'C28 H48 B3 N7'
_chemical_formula_weight         515.16
_chemical_name_systematic        3-Xyl
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-13
_audit_creation_method           'CIF-fill 1.4a (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                 99.6820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.26690(10)
_cell_length_b                   10.93410(10)
_cell_length_c                   30.2037(2)
_cell_measurement_reflns_used    42279
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.8780
_cell_measurement_theta_min      2.9570
_cell_volume                     6272.27(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.63a (Rigaku OD, 2023)'
_computing_data_collection
;
 CrysAlisPro system (CCD 42.72a 64-bit (release 07-10-2022))
;
_computing_data_reduction        'CrysAlisPro 1.171.43.63a (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 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     42.00  93.00   0.50    0.14    --   85.25 -98.00 -35.07  102
  2  \w     39.00 101.00   0.50    0.14    --   85.25-125.00  49.61  124
  3  \w     42.00  93.00   0.50    0.14    --   85.25 -98.00  88.88  102
  4  \w     42.00  93.00   0.50    0.14    --   85.25 -97.00 168.12  102
  5  \w     37.00  93.00   0.50    0.14    --   82.28-112.00 120.00  112
  6  \w     40.00  90.00   0.50    0.14    --   82.28 -95.00 120.00  100
  7  \w     40.00  90.00   0.50    0.14    --   82.28 -95.00  60.00  100
  8  \w     40.00  90.00   0.50    0.14    --   82.28 -95.00  30.00  100
  9  \w     40.00  90.00   0.50    0.14    --   82.28 -95.00 -60.00  100
 10  \w     40.00  90.00   0.50    0.14    --   82.28 -95.00 -90.00  100
 11  \w     40.00  90.00   0.50    0.14    --   82.28 -95.00-120.00  100
 12  \w     40.00  90.00   0.50    0.14    --   82.28 -95.00-150.00  100
 13  \w     16.00  66.00   0.50    0.14    --   58.57 -95.00-120.00  100
 14  \w     50.00 135.00   0.50    0.14    --   85.25  14.00  24.57  170
 15  \w     73.00 137.00   0.50    0.14    --   85.25  21.00-141.65  128
 16  \w     97.00 132.00   0.50    0.14    --   85.25 124.00-137.56   70
 17  \w     98.00 132.00   0.50    0.14    --   85.25 122.00 -81.21   68
 18  \w    102.00 131.00   0.50    0.14    --   85.25 115.00  -6.85   58
 19  \w     59.00  94.00   0.50    0.14    --   46.00  52.00  74.19   70
 20  \w     34.00  60.00   0.50    0.14    --   22.00  59.00  48.38   52
 21  \w     34.00  60.00   0.50    0.14    --   22.00  59.00   8.45   52
 22  \w     34.00  60.00   0.50    0.14    --   22.00  57.00 -46.95   52
 23  \w   -102.00 -33.00   0.50    0.14    --  -79.50 132.00  71.53  138
 24  \w    -93.00 -35.00   0.50    0.14    --  -79.50 106.00 117.52  116
 25  \w    -99.00 -32.00   0.50    0.14    --  -79.50 121.00  -3.51  134
 26  \w   -100.00 -33.00   0.50    0.14    --  -79.50 123.00 -71.61  134
 27  \w    -97.00 -33.00   0.50    0.14    --  -79.50 117.00-167.61  128
 28  \w    -91.00 -35.00   0.50    0.14    --  -79.50 101.00 -66.37  112
 29  \w   -131.00 -68.00   0.50    0.14    --  -79.50 -21.00 -25.26  126
 30  \w   -125.00 -91.00   0.50    0.14    --  -79.50 -60.00 -55.55   68
 31  \w   -125.00 -91.00   0.50    0.14    --  -79.50 -60.00-158.28   68
 32  \w   -126.00 -91.00   0.50    0.14    --  -79.50 -58.00 -27.66   70
 33  \w   -125.00 -91.00   0.50    0.14    --  -79.50 -61.00  17.46   68
 34  \w   -122.00 -87.00   0.50    0.14    --  -74.00 -52.00  94.06   70
 35  \w   -124.00 -94.00   0.50    0.14    --  -79.50 -64.00 155.41   60
 36  \w    -74.00 -39.00   0.50    0.14    --  -26.00 -52.00 115.24   70
 37  \w   -102.00 -67.00   0.50    0.14    --  -54.00 -52.00  65.61   70
 38  \w   -128.00 -93.00   0.50    0.14    --  -79.50 -50.00  60.77   70
 39  \w   -110.00 -75.00   0.50    0.14    --  -62.00 -51.00 -42.04   70
 40  \w   -106.00 -71.00   0.50    0.14    --  -58.00 -51.00-170.41   70
 41  \w    -74.00 -39.00   0.50    0.14    --  -26.00 -51.00-158.85   70
 42  \w   -124.00 -87.00   0.50    0.14    --  -74.00 -44.00 -95.88   74
 43  \w   -129.00 -92.00   0.50    0.14    --  -79.50 -44.00-141.22   74
 44  \w   -130.00 -90.00   0.50    0.14    --  -79.50 -38.00-118.37   80
 45  \w   -107.00 -72.00   0.50    0.14    --  -58.00 -50.00 -71.72   70
 46  \w   -119.00 -84.00   0.50    0.14    --  -70.00 -47.00 128.71   70
 47  \w   -120.00 -83.00   0.50    0.14    --  -70.00 -45.00 162.53   74
 48  \w   -130.00 -91.00   0.50    0.14    --  -79.50 -41.00 107.23   78
 49  \w   -126.00 -93.00   0.50    0.14    --  -79.50-120.00 -68.50   66
 50  \w   -126.00 -85.00   0.50    0.14    --  -79.50-136.00-173.31   82
 51  \w   -126.00 -85.00   0.50    0.14    --  -79.50-137.00-136.36   82
 52  \w   -126.00 -86.00   0.50    0.14    --  -79.50-134.00  59.66   80
 53  \w   -127.00 -90.00   0.50    0.14    --  -79.50-126.00 136.77   74
;
_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      0.0454475000
_diffrn_orient_matrix_UB_12      -0.0728553000
_diffrn_orient_matrix_UB_13      -0.0281429000
_diffrn_orient_matrix_UB_21      -0.0298839000
_diffrn_orient_matrix_UB_22      -0.1205522000
_diffrn_orient_matrix_UB_23      0.0153836000
_diffrn_orient_matrix_UB_31      -0.0601594000
_diffrn_orient_matrix_UB_32      0.0048352000
_diffrn_orient_matrix_UB_33      -0.0405839000
_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  0.0256
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            57795
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         2.968
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.43.63a (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            orange
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_preparation
;
 Crystals were grown at -30?C \%C from saturated solution in pentane. 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          0.370
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.34(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     714
_refine_ls_number_reflns         10126
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0466P)^2^+1.0685P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0716
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.772
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                9917
_reflns_number_total             10126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03752b2.cif
_cod_data_source_block           NiHe005_NiHe_a
_cod_depositor_comments
'Adding full bibliography for 1575379--1575386.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1575386
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.838
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              34935