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_1575381
_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         'C27 H46 B3 N7 O, 0.5 (C5 H12)'
_chemical_formula_sum            'C29.5 H52 B3 N7 O'
_chemical_formula_weight         553.21
_chemical_name_systematic        3-PhOMe
_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
_audit_creation_date             2025-04-15
_audit_creation_method           'CIF-fill 1.6d (K.Radacki, 2005-25)'
_audit_update_record
;
2025-07-01 deposited with the CCDC.	2025-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                69.387(2)
_cell_angle_beta                 79.424(2)
_cell_angle_gamma                79.155(2)
_cell_formula_units_Z            2
_cell_length_a                   10.9804(3)
_cell_length_b                   12.3739(3)
_cell_length_c                   12.9690(4)
_cell_measurement_reflns_used    18434
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.3220
_cell_measurement_theta_min      3.6630
_cell_volume                     1606.59(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-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 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
 
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     98.00 129.00   0.50    0.19    --   85.25 122.00 165.72   62
  2  \w    102.00 129.00   0.50    0.19    --   82.28  15.00   0.00   54
  3  \w     63.00  97.00   0.50    0.19    --   82.28  15.00   0.00   68
  4  \w     93.00 133.00   0.50    0.19    --   82.28  15.00-180.00   80
  5  \w     38.00 102.00   0.50    0.19    --   85.25-129.00-110.77  128
  6  \w     42.00  93.00   0.50    0.19    --   85.25 -98.00-158.35  102
  7  \w     36.00 100.00   0.50    0.19    --   82.28-124.00 -15.00  128
  8  \w     55.00  86.00   0.50    0.19    --   82.28 -95.00-120.00   62
  9  \w     25.00  97.00   0.50    0.19    --   71.14-124.00 -15.00  144
 10  \w     40.00  87.00   0.50    0.19    --   82.28 -95.00 -60.00   94
 11  \w     40.00  70.00   0.50    0.19    --   82.28 -95.00 -90.00   60
 12  \w     19.00  84.00   0.50    0.19    --   58.28-124.00 -15.00  130
 13  \w     58.00  90.00   0.50    0.19    --   82.28 -95.00  60.00   64
 14  \w     37.00  93.00   0.50    0.19    --   82.28-112.00  90.00  112
 15  \w     51.00  93.00   0.50    0.19    --   85.25 -97.00 160.45   84
 16  \w     41.00  75.00   0.50    0.19    --   82.28 -95.00 150.00   68
 17  \w     51.00  77.00   0.50    0.19    --   82.28 -95.00 120.00   52
 18  \w     44.00  80.00   0.50    0.19    --   82.28 -95.00  90.00   72
 19  \w     46.00  90.00   0.50    0.19    --   82.28 -95.00 -30.00   88
 20  \w     28.00  79.00   0.50    0.19    --   71.14 -95.00-120.00  102
 21  \w    -94.00 -59.00   0.50    0.19    --  -46.00 -51.00  -3.33   70
 22  \w    -99.00 -64.00   0.50    0.19    --  -50.00 -47.00-107.59   70
 23  \w    -95.00 -60.00   0.50    0.19    --  -46.00 -48.00 108.33   70
 24  \w   -100.00 -63.00   0.50    0.19    --  -50.00 -45.00 121.07   74
 25  \w   -105.00 -65.00   0.50    0.19    --  -54.00 -36.00 -66.08   80
 26  \w   -124.00 -92.00   0.50    0.19    --  -79.50 -63.00-130.01   64
 27  \w   -126.00 -92.00   0.50    0.19    --  -79.50 -57.00-147.71   68
 28  \w   -118.00 -83.00   0.50    0.19    --  -70.00 -54.00 -10.13   70
 29  \w   -127.00 -91.00   0.50    0.19    --  -79.50 -56.00 -11.17   72
 30  \w   -127.00 -92.00   0.50    0.19    --  -79.50 -54.00 -32.68   70
 31  \w   -125.00 -91.00   0.50    0.19    --  -79.50 -61.00  17.56   68
 32  \w   -128.00 -93.00   0.50    0.19    --  -79.50 -50.00-108.91   70
 33  \w   -110.00 -75.00   0.50    0.19    --  -62.00 -51.00  63.92   70
 34  \w   -128.00 -93.00   0.50    0.19    --  -79.50 -50.00 -48.74   70
 35  \w   -127.00 -91.00   0.50    0.19    --  -79.50 -56.00  82.89   72
 36  \w   -128.00 -93.00   0.50    0.19    --  -79.50 -50.00  97.03   70
 37  \w   -127.00 -92.00   0.50    0.19    --  -79.50 -54.00 132.84   70
 38  \w   -107.00 -72.00   0.50    0.19    --  -58.00 -50.00 172.91   70
 39  \w   -130.00 -91.00   0.50    0.19    --  -79.50 -41.00 158.46   78
 40  \w   -129.00 -93.00   0.50    0.19    --  -79.50 -47.00  52.20   72
 41  \w   -111.00 -76.00   0.50    0.19    --  -62.00 -49.00-120.49   70
 42  \w   -124.00 -86.00   0.50    0.19    --  -74.00 -41.00-148.66   76
 43  \w   -126.00 -93.00   0.50    0.19    --  -79.50-120.00-142.36   66
 44  \w   -126.00 -93.00   0.50    0.19    --  -79.50-121.00-120.37   66
 45  \w   -127.00 -90.00   0.50    0.19    --  -79.50-127.00 -63.08   74
 46  \w   -126.00 -93.00   0.50    0.19    --  -79.50-121.00 -43.97   66
 47  \w    -92.00 -31.00   0.50    0.19    --  -76.35 112.00   0.00  122
 48  \w    -98.00 -33.00   0.50    0.19    --  -79.50 119.00-130.69  130
 49  \w    -86.00 -13.00   0.50    0.19    --  -59.96 124.00  63.00  146
 50  \w    -99.00 -32.00   0.50    0.19    --  -79.50 122.00 172.26  134
 51  \w    -95.00 -23.00   0.50    0.19    --  -69.45 124.00  63.00  144
 52  \w    -97.00 -33.00   0.50    0.19    --  -79.50 115.00  60.36  128
 53  \w    -97.00 -33.00   0.50    0.19    --  -79.50 117.00  67.99  128
 54  \w    -99.00 -30.00   0.50    0.19    --  -76.35 124.00  63.00  138
 55  \w    -97.00 -33.00   0.50    0.19    --  -79.50 115.00 -40.14  128
;
_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      -0.0239001000
_diffrn_orient_matrix_UB_12      0.0109342000
_diffrn_orient_matrix_UB_13      0.1169672000
_diffrn_orient_matrix_UB_21      0.0397359000
_diffrn_orient_matrix_UB_22      -0.1320691000
_diffrn_orient_matrix_UB_23      0.0505965000
_diffrn_orient_matrix_UB_31      0.1363616000
_diffrn_orient_matrix_UB_32      0.0213647000
_diffrn_orient_matrix_UB_33      -0.0114900000
_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  0.0268
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31770
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.076
_diffrn_reflns_theta_min         3.671
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.474
_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            'clear intense orange'
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       plate
_exptl_crystal_F_000             602
_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          0.350
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6029
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0644P)^2^+0.4785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5288
_reflns_number_total             6029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03752b2.cif
_cod_data_source_block           NiHe006_NiHe_a
_cod_depositor_comments
'Adding full bibliography for 1575379--1575386.cif.'
_cod_database_code               1575381
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.834
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              25982