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_1576383
_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         'C31 H27 B, 0.5(C6 H6)'
_chemical_formula_sum            'C34 H30 B'
_chemical_formula_weight         449.39
_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             2025-02-20
_audit_creation_method           'CIF-fill 1.5r (K.Radacki, 2005-25)'
_audit_update_record
;
2025-11-03 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.16220(10)
_cell_length_b                   15.8236(2)
_cell_length_c                   13.14960(10)
_cell_measurement_reflns_used    18718
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.6530
_cell_measurement_theta_min      4.3560
_cell_volume                     2525.96(4)
_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-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 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     42.00  91.00   0.50    0.08    --   84.76 -95.00-120.00   98
  2  \w     38.00  63.00   0.50    0.08    --   77.01-113.00 130.00   50
  3  \w     18.00  44.00   0.50    0.08    --   58.85 -95.00-150.00   52
  4  \w   -110.00 -56.00   0.50    0.08    --  -60.43 -15.00 150.00  108
  5  \w   -104.00 -42.00   0.50    0.08    --  -76.45 -15.00-150.00  124
  6  \w   -125.00 -43.00   0.50    0.08    --  -76.45 -15.00  30.00  164
  7  \w     16.00  55.00   0.50    0.08    --   58.85 -95.00 150.00   78
  8  \w     43.00  81.00   0.50    0.08    --   58.85  15.00  90.00   76
  9  \w     67.00  92.00   0.50    0.08    --   84.76 -95.00-150.00   50
 10  \w     49.00 125.00   0.50    0.08    --   84.76  15.00   0.00  152
 11  \w    -64.00 -38.00   0.50    0.08    --  -69.92 -15.00  90.00   52
 12  \w     32.00  88.00   0.50    0.08    --   77.01-112.00   0.00  112
 13  \w    -80.00 -55.00   0.50    0.08    --  -69.92 113.00-138.00   50
 14  \w     53.00  89.00   0.50    0.08    --   84.76 -95.00 -90.00   72
 15  \w     28.00  55.00   0.50    0.08    --   58.85-113.00 130.00   54
 16  \w    -86.00 -61.00   0.50    0.08    --  -76.45 113.00-138.00   50
 17  \w    -93.00 -42.00   0.50    0.08    --  -69.92 -15.00  60.00  102
 18  \w    -93.00 -34.00   0.50    0.08    --  -76.45 112.00-150.00  118
 19  \w    -75.00 -15.00   0.50    0.08    --  -60.43 113.00-138.00  120
 20  \w    -68.00 -43.00   0.50    0.08    --  -76.45 112.00 -30.00   50
 21  \w    -60.00 -26.00   0.50    0.08    --  -69.92 126.00 -30.00   68
 22  \w    -57.00 -26.00   0.50    0.08    --  -69.92 126.00   0.00   62
 23  \w    -93.00 -36.00   0.50    0.08    --  -76.45 112.00   0.00  114
 24  \w     39.00  64.00   0.50    0.08    --   84.76-112.00 150.00   50
 25  \w   -118.00 -93.00   0.50    0.08    --  -69.92 -15.00  90.00   50
 26  \w   -127.00 -41.00   0.50    0.08    --  -76.45 -15.00 120.00  172
 27  \w     58.00  91.00   0.50    0.08    --   71.50-113.00 130.00   66
 28  \w     67.00  92.00   0.50    0.08    --   84.76 -95.00  90.00   50
 29  \w     53.00 135.00   0.50    0.08    --   84.76  15.00 -90.00  164
 30  \w     41.00  77.00   0.50    0.08    --   77.01  15.00  60.00   72
 31  \w     92.00 123.00   0.50    0.08    --   77.01  15.00  60.00   62
 32  \w     39.00  64.00   0.50    0.08    --   84.76-112.00-120.00   50
 33  \w     35.00  84.00   0.50    0.08    --   77.01 -95.00  90.00   98
 34  \w     62.00  91.00   0.50    0.08    --   84.76 -95.00-180.00   58
 35  \w     65.00  90.00   0.50    0.08    --   84.76 -95.00 -30.00   50
 36  \w     48.00  91.00   0.50    0.08    --   84.76 -95.00  60.00   86
 37  \w     42.00  67.00   0.50    0.08    --   84.76-113.00 130.00   50
 38  \w     16.00  64.00   0.50    0.08    --   58.85 -95.00 -30.00   96
 39  \w     45.00  92.00   0.50    0.08    --   84.76 -95.00 150.00   94
 40  \w     42.00  91.00   0.50    0.08    --   84.76 -95.00 -60.00   98
 41  \w     66.00  92.00   0.50    0.08    --   84.76 -95.00   0.00   52
 42  \w     34.00  77.00   0.50    0.08    --   77.01 -95.00-180.00   86
;
_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      -0.0250713000
_diffrn_orient_matrix_UB_12      0.0954051000
_diffrn_orient_matrix_UB_13      -0.0056631000
_diffrn_orient_matrix_UB_21      -0.0661752000
_diffrn_orient_matrix_UB_22      -0.0071068000
_diffrn_orient_matrix_UB_23      0.0958723000
_diffrn_orient_matrix_UB_31      0.1053593000
_diffrn_orient_matrix_UB_32      0.0181682000
_diffrn_orient_matrix_UB_33      0.0674003000
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36391
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.136
_diffrn_reflns_theta_min         4.377
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77197
_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 colourless'
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_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          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0621P)^2^+0.7368P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4299
_reflns_number_total             5069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08526h2.cif
_cod_data_source_block           5TolMe
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1576383
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.912
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              7328