N–H / P–H bond activation of ammonia, amines and phosphines at a transient borylene
Weber, Marco; Kar, Sourav; Joos, Pia; Dewhurst, Rian David; Braunschweig, Holger; Chemical Science  (2026) –; doi:10.1039/D6SC00526H

data_1576633
_publ_section_title
;
 N-H/P-H bond activation of ammonia, amines and phosphines at a transient
 borylene.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              8189
_journal_page_last               8196
_journal_paper_doi               10.1039/d6sc00526h
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C32 H51 B N2'
_chemical_formula_sum            'C32 H51 B N2'
_chemical_formula_weight         474.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-09-20
_audit_creation_method           'CIF-fill 1.5c (K.Radacki, 2005-23)'
_audit_update_record
;
2026-01-07 deposited with the CCDC.	2026-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.499(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5748(2)
_cell_length_b                   25.2253(4)
_cell_length_c                   12.8086(2)
_cell_measurement_reflns_used    24872
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.8720
_cell_measurement_theta_min      3.4540
_cell_volume                     2966.24(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_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 0.982
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -83.00 -55.00   0.50    1.64    --  -38.00 -40.00 152.33   56
  2  \w     57.00  83.00   0.50    1.64    --   38.00  45.00  93.31   52
  3  \w    -88.00 -59.00   0.50    1.64    --  -42.00 -38.00 -69.82   58
  4  \w    -91.00 -64.00   0.50    1.64    --  -46.00 -42.00 -86.63   54
  5  \w    -64.00 -10.00   0.50    1.64    --  -50.00 115.00  72.91  108
  6  \w    -65.00 -10.00   0.50    1.64    --  -50.00 116.00 -45.13  110
  7  \w   -103.00 -76.00   0.50    1.64    --  -58.00 -44.00 -26.78   54
  8  \w   -103.00 -76.00   0.50    1.64    --  -58.00 -43.00 -44.53   54
  9  \w   -103.00 -76.00   0.50    1.64    --  -58.00 -44.00 -79.90   54
 10  \w   -103.00 -76.00   0.50    1.64    --  -58.00 -43.00 -59.86   54
 11  \w     19.00  80.00   0.50    1.64    --   60.09-125.00  60.00  122
 12  \w     19.00  80.00   0.50    1.64    --   60.09-125.00  90.00  122
 13  \w    -82.00 -21.00   0.50    1.64    --  -61.72 125.00  60.00  122
 14  \w    -82.00 -21.00   0.50    1.64    --  -61.72 125.00  90.00  122
 15  \w   -107.00 -80.00   0.50    1.64    --  -62.00 -43.00-166.40   54
 16  \w   -111.00 -84.00   0.50    1.64    --  -66.00 -44.00 -88.10   54
 17  \w   -111.00 -84.00   0.50    1.64    --  -66.00 -44.00 -63.67   54
 18  \w   -117.00 -86.00   0.50    1.64    --  -70.00 -38.00  -3.68   62
 19  \w   -115.00 -88.00   0.50    1.64    --  -70.00 -43.00 153.79   54
 20  \w   -115.00 -88.00   0.50    1.64    --  -70.00 -43.00 -73.41   54
 21  \w   -117.00 -86.00   0.50    1.64    --  -70.00 -34.00 101.40   62
 22  \w   -116.00 -88.00   0.50    1.64    --  -70.00 -41.00-177.14   56
 23  \w   -117.00 -86.00   0.50    1.64    --  -70.00 -38.00  67.11   62
 24  \w   -117.00 -86.00   0.50    1.64    --  -70.00 -31.00-121.28   62
 25  \w   -117.00 -55.00   0.50    1.64    --  -71.97 -15.00  90.00  124
 26  \w    -92.00 -31.00   0.50    1.64    --  -71.97 125.00 -90.00  122
 27  \w    -92.00 -31.00   0.50    1.64    --  -71.97 125.00-120.00  122
 28  \w     33.00  94.00   0.50    1.64    --   73.60-125.00   0.00  122
 29  \w   -119.00 -92.00   0.50    1.64    --  -74.00 -41.00 -92.94   54
 30  \w   -121.00 -90.00   0.50    1.64    --  -74.00 -30.00  24.52   62
 31  \w   -119.00 -92.00   0.50    1.64    --  -74.00 -41.00 -48.47   54
 32  \w     51.00 120.00   0.50    1.64    --   75.05  15.00  90.00  138
 33  \w   -120.00 -58.00   0.50    1.64    --  -75.12 -15.00  60.00  124
 34  \w   -120.00 -58.00   0.50    1.64    --  -75.12 -15.00 -60.00  124
 35  \w    -95.00 -34.00   0.50    1.64    --  -75.12 125.00-180.00  122
 36  \w   -124.00 -96.00   0.50    1.64    --  -78.50 -42.00-175.41   56
 37  \w   -102.00 -37.00   0.50    1.64    --  -78.50 129.00 -71.26  130
 38  \w   -108.00 -37.00   0.50    1.64    --  -78.50 138.00  25.33  142
 39  \w   -126.00 -95.00   0.50    1.64    --  -78.50 -31.00  40.34   62
 40  \w   -103.00 -37.00   0.50    1.64    --  -78.50 131.00  64.50  132
 41  \w   -123.00 -97.00   0.50    1.64    --  -78.50 -44.00 -45.50   52
 42  \w   -125.00 -96.00   0.50    1.64    --  -78.50 -41.00-119.93   58
 43  \w   -123.00 -97.00   0.50    1.64    --  -78.50 -45.00 -56.03   52
 44  \w   -109.00 -38.00   0.50    1.64    --  -78.50 140.00 108.98  142
 45  \w   -123.00 -97.00   0.50    1.64    --  -78.50 -45.00 -95.84   52
 46  \w   -123.00 -97.00   0.50    1.64    --  -78.50 -44.00 -62.50   52
 47  \w   -124.00 -96.00   0.50    1.64    --  -78.50 -39.00 -86.00   56
 48  \w   -108.00 -38.00   0.50    1.64    --  -78.50 139.00  74.61  140
 49  \w   -125.00 -92.00   0.50    1.64    --  -78.50 -27.00 -75.62   66
 50  \w   -123.00 -97.00   0.50    1.64    --  -78.50 -44.00 -30.14   52
 51  \w     39.00  91.00   0.50    1.64    --   79.22-110.00  44.13  104
 52  \w    -13.00  13.00   0.50    1.64    --  -18.00  86.00-171.33   52
 53  \w    -79.00 -51.00   0.50    1.64    --  -34.00 -40.00 -20.05   56
 54  \w    -84.00 -55.00   0.50    1.64    --  -38.00 -39.00-176.73   58
 55  \w    -84.00 -55.00   0.50    1.64    --  -38.00 -39.00-144.78   58
 56  \w    -87.00 -59.00   0.50    1.64    --  -42.00 -40.00 105.19   56
 57  \w     65.00  91.00   0.50    1.64    --   46.00  45.00 116.11   52
 58  \w   -117.00 -86.00   0.50    1.64    --  -70.00 -31.00-160.20   62
;
_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      -0.0534612000
_diffrn_orient_matrix_UB_12      -0.0254644000
_diffrn_orient_matrix_UB_13      -0.1137285000
_diffrn_orient_matrix_UB_21      0.1068490000
_diffrn_orient_matrix_UB_22      0.0348814000
_diffrn_orient_matrix_UB_23      -0.0396934000
_diffrn_orient_matrix_UB_31      0.1177884000
_diffrn_orient_matrix_UB_32      -0.0431783000
_diffrn_orient_matrix_UB_33      0.0350237000
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            56510
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.292
_diffrn_reflns_theta_min         3.504
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) 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            'light red'
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_preparation
;
 Crystals were grown at 25 \%C from saturated solution in benzene. 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_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0557P)^2^+0.7296P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4978
_reflns_number_total             5842
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc00526h2.cif
_cod_data_source_block           MaWe108_MaWe_a
_cod_depositor_comments
'Adding full bibliography for 1576631--1576636.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1576633
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              66560