Synthesis of symmetrical and unsymmetrical cyclic diborenes via NHC-directed C–H borylation
Mihm, Cornelius; Kar, Sourav; Sachs, Andreas; Duwe, Dario; Dewhurst, Rian D.; Braunschweig, Holger; Chemical Science 16 (2025) 11637–11643; doi:10.1039/D5SC03150H

data_1574720
_publ_section_title
;
 Synthesis of symmetrical and unsymmetrical cyclic diborenes via
 NHC-directed C--H borylation
;
_journal_issue                   25
_journal_name_full               'Chemical Science'
_journal_page_first              11637
_journal_page_last               11643
_journal_paper_doi               10.1039/D5SC03150H
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C22 H27 B I2 N2, C7 H8'
_chemical_formula_sum            'C29 H35 B I2 N2'
_chemical_formula_weight         676.22
_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             2024-11-04
_audit_creation_method           'CIF-fill 1.5k (K.Radacki, 2005-24)'
_audit_update_record
;
2025-04-29 deposited with the CCDC.	2025-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                81.4500(10)
_cell_angle_beta                 76.195(2)
_cell_angle_gamma                82.5200(10)
_cell_formula_units_Z            2
_cell_length_a                   8.20520(10)
_cell_length_b                   10.8597(2)
_cell_length_c                   16.6641(3)
_cell_measurement_reflns_used    10737
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.9370
_cell_measurement_theta_min      4.1270
_cell_volume                     1419.00(4)
_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 0.993
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     21.00  58.00   0.50    0.05    --   58.77 -95.00 -90.00   74
  2  \w     20.00  46.00   0.50    0.05    --   58.77 -95.00  90.00   52
  3  \w     17.00  53.00   0.50    0.05    --   58.77 -95.00 -30.00   72
  4  \w     17.00  54.00   0.50    0.05    --   58.77 -95.00-180.00   74
  5  \w     19.00  45.00   0.50    0.05    --   58.77 -95.00  30.00   52
  6  \w    -61.00 -28.00   0.50    0.05    --  -60.22 126.00   0.00   66
  7  \w    -59.00 -33.00   0.50    0.05    --  -60.22 -15.00 120.00   52
  8  \w   -118.00 -92.00   0.50    0.05    --  -69.97 -15.00 -90.00   52
  9  \w    -68.00 -40.00   0.50    0.05    --  -69.97 -15.00 -90.00   56
 10  \w    -49.00 -23.00   0.50    0.05    --  -69.97 126.00 -90.00   52
 11  \w     30.00  55.00   0.50    0.05    --   71.55 -95.00-120.00   50
 12  \w     32.00  66.00   0.50    0.05    --   71.55-126.00 -90.00   68
 13  \w     35.00  68.00   0.50    0.05    --   71.55 -95.00 150.00   66
 14  \w     27.00  64.00   0.50    0.05    --   71.55-126.00 150.00   74
 15  \w     72.00  98.00   0.50    0.05    --   71.55-126.00 -90.00   52
 16  \w   -126.00 -44.00   0.50    0.05    --  -76.33 -15.00-150.00  164
 17  \w   -127.00 -40.00   0.50    0.05    --  -76.33 -15.00 120.00  174
 18  \w     39.00  64.00   0.50    0.05    --   77.28 -95.00  30.00   50
 19  \w     33.00  83.00   0.50    0.05    --   77.28-112.00  90.00  100
 20  \w     38.00  64.00   0.50    0.05    --   77.28 -95.00-180.00   52
 21  \w     32.00  62.00   0.50    0.05    --   77.28-112.00   0.00   60
 22  \w     32.00  97.00   0.50    0.05    --   78.00-114.00 147.97  130
 23  \w    -97.00 -65.00   0.50    0.05    --  -79.50 116.00 -54.39   64
 24  \w     45.00  87.00   0.50    0.05    --   85.03 -95.00 120.00   84
 25  \w     49.00 133.00   0.50    0.05    --   85.03  15.00 150.00  168
 26  \w     66.00  92.00   0.50    0.05    --   85.03 -95.00   0.00   52
 27  \w     62.00  92.00   0.50    0.05    --   85.03 -95.00-180.00   60
 28  \w     43.00  92.00   0.50    0.05    --   85.03 -95.00-150.00   98
 29  \w     67.00  92.00   0.50    0.05    --   85.03 -95.00  60.00   50
 30  \w     42.00  92.00   0.50    0.05    --   85.03 -95.00 -60.00  100
 31  \w     58.00 135.00   0.50    0.05    --   85.03  15.00  60.00  154
 32  \w     65.00  90.00   0.50    0.05    --   85.03 -95.00 -30.00   50
 33  \w     67.00  92.00   0.50    0.05    --   85.03 -95.00-120.00   50
 34  \w     42.00  67.00   0.50    0.05    --   85.03 -95.00 -90.00   50
;
_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      0.1001738000
_diffrn_orient_matrix_UB_12      0.0513688000
_diffrn_orient_matrix_UB_13      -0.0863427000
_diffrn_orient_matrix_UB_21      0.1484263000
_diffrn_orient_matrix_UB_22      -0.0994254000
_diffrn_orient_matrix_UB_23      0.0095433000
_diffrn_orient_matrix_UB_31      -0.0753784000
_diffrn_orient_matrix_UB_32      -0.0908682000
_diffrn_orient_matrix_UB_33      -0.0406661000
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15820
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.086
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    17.536
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.731
_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            colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_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_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5517
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0233
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+1.1623P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5190
_reflns_number_total             5517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03150h2.cif
_cod_data_source_block           diodoborane_4
_cod_depositor_comments
'Adding full bibliography for 1574720--1574725.cif.'
_cod_database_code               1574720
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.273
_shelx_estimated_absorpt_t_max   0.474
_shelx_res_checksum              51344