Boraindenes as versatile precursors to benzannulated boron heterocycles
Wieprecht, Nele; Krummenacher, Ivo; Wüst, Leonie; Michel, Maximilian; Neder, Marco; Häfner, Andreas; Karg, Jordan; Braunschweig, Holger; Chemical Science  (2025) –; doi:10.1039/D5SC08526H

data_1576365
_publ_section_title
;
 Boraindenes as versatile precursors to benzannulated boron heterocycles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC08526H
_journal_year                    2025
_chemical_formula_moiety         'C30 H27 B, C5 H12'
_chemical_formula_sum            'C35 H39 B'
_chemical_formula_weight         470.47
_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             2024-10-02
_audit_creation_method           'CIF-fill 1.5g (K.Radacki, 2005-23)'
_audit_update_record
;
2025-11-03 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                106.738(3)
_cell_angle_beta                 90.918(3)
_cell_angle_gamma                99.982(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5538(4)
_cell_length_b                   10.0705(3)
_cell_length_c                   15.4814(5)
_cell_measurement_reflns_used    9006
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.4850
_cell_measurement_theta_min      2.9720
_cell_volume                     1401.35(9)
_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 0.989
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     35.00 107.00   0.50    0.10    --   76.88-140.00-155.00  144
  2  \w     36.00  61.00   0.50    0.10    --   58.63-140.00-155.00   50
  3  \w     43.00  68.00   0.50    0.10    --   71.40-140.00-155.00   50
  4  \w     50.00  99.00   0.50    0.10    --   80.80-122.00-129.95   98
  5  \w     72.00  99.00   0.50    0.10    --   76.88-131.00  18.00   54
  6  \w     33.00  59.00   0.50    0.10    --   58.63-126.00  60.00   52
  7  \w     21.00  82.00   0.50    0.10    --   58.63-126.00  90.00  122
  8  \w     44.00  91.00   0.50    0.10    --   76.88-112.00  90.00   94
  9  \w     41.00  67.00   0.50    0.10    --   76.88-112.00  30.00   52
 10  \w     30.00  55.00   0.50    0.10    --   58.63-131.00  18.00   50
 11  \w     39.00  90.00   0.50    0.10    --   76.88-112.00 -30.00  102
 12  \w     51.00  98.00   0.50    0.10    --   80.80-119.00 -86.25   94
 13  \w     61.00 107.00   0.50    0.10    --   76.88  15.00  30.00   92
 14  \w     45.00 122.00   0.50    0.10    --   76.88  15.00  90.00  154
 15  \w     64.00  89.00   0.50    0.10    --   76.88  15.00 150.00   50
 16  \w     74.00 120.00   0.50    0.10    --   76.88  15.00 -30.00   92
 17  \w    -68.00 -39.00   0.50    0.10    --  -60.27 140.00 -96.00   58
 18  \w    -81.00 -49.00   0.50    0.10    --  -69.75 140.00 -96.00   64
 19  \w    -92.00 -66.00   0.50    0.10    --  -75.18 140.00 -96.00   52
 20  \w    -55.00 -18.00   0.50    0.10    --  -60.27 126.00-150.00   74
 21  \w    -85.00 -60.00   0.50    0.10    --  -69.75 131.00  89.00   50
 22  \w    -91.00 -66.00   0.50    0.10    --  -75.18 131.00  89.00   50
 23  \w    -77.00 -27.00   0.50    0.10    --  -69.75 126.00 150.00  100
 24  \w    -61.00 -36.00   0.50    0.10    --  -78.50 118.00 173.54   50
 25  \w    -51.00 -22.00   0.50    0.10    --  -60.27 131.00  89.00   58
 26  \w    -97.00 -66.00   0.50    0.10    --  -78.50 118.00 173.54   62
 27  \w    -99.00 -42.00   0.50    0.10    --  -78.50 122.00  66.59  114
 28  \w    -86.00 -35.00   0.50    0.10    --  -75.18 112.00  30.00  102
 29  \w    -97.00 -48.00   0.50    0.10    --  -78.50 118.00  48.58   98
 30  \w    -98.00 -52.00   0.50    0.10    --  -78.50 121.00 -23.20   92
 31  \w    -89.00 -34.00   0.50    0.10    --  -75.18 112.00-120.00  110
 32  \w   -106.00 -35.00   0.50    0.10    --  -60.27 -15.00 -60.00  142
 33  \w    -91.00 -55.00   0.50    0.10    --  -60.27 -15.00-120.00   72
 34  \w    -73.00 -40.00   0.50    0.10    --  -69.75 -15.00-150.00   66
 35  \w   -109.00 -84.00   0.50    0.10    --  -69.75 -15.00-150.00   50
 36  \w   -115.00 -37.00   0.50    0.10    --  -69.75 -15.00  30.00  156
 37  \w   -104.00 -44.00   0.50    0.10    --  -75.18 -15.00  90.00  120
 38  \w    -96.00 -47.00   0.50    0.10    --  -75.18 -15.00 150.00   98
;
_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      -0.1100399000
_diffrn_orient_matrix_UB_12      0.0650567000
_diffrn_orient_matrix_UB_13      0.0623539000
_diffrn_orient_matrix_UB_21      0.0992484000
_diffrn_orient_matrix_UB_22      0.0168369000
_diffrn_orient_matrix_UB_23      0.0833873000
_diffrn_orient_matrix_UB_31      0.0705702000
_diffrn_orient_matrix_UB_32      0.1480409000
_diffrn_orient_matrix_UB_33      -0.0031050000
_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  0.0428
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17960
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.013
_diffrn_reflns_theta_min         2.988
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_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          0.270
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5278
_refine_ls_number_restraints     163
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0850
_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^)+(0.1991P)^2^] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2517
_refine_ls_wR_factor_ref         0.2749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3820
_reflns_number_total             5278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08526h2.cif
_cod_data_source_block           1Dur
_cod_database_code               1576365
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.956
_shelx_res_checksum              52396