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_1576382
_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         'C41 H31 B, 0.5(C6 H6)'
_chemical_formula_sum            'C44 H34 B'
_chemical_formula_weight         573.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-09-25
_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                90
_cell_angle_beta                 91.4100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1092(3)
_cell_length_b                   14.4261(2)
_cell_length_c                   23.5455(4)
_cell_measurement_reflns_used    21469
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.4280
_cell_measurement_theta_min      3.7330
_cell_volume                     6488.85(18)
_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 0.968
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     42.00  71.00   0.50    0.10    --   58.93  15.00 120.00   58
  2  \w     81.00 106.00   0.50    0.10    --   58.93  15.00 120.00   50
  3  \w     95.00 121.00   0.50    0.10    --   76.88  15.00 -90.00   52
  4  \w     58.00 121.00   0.50    0.10    --   76.88  15.00-120.00  126
  5  \w     38.00  96.00   0.50    0.10    --   58.93  15.00-150.00  116
  6  \w     46.00 124.00   0.50    0.10    --   76.88  15.00   0.00  156
  7  \w     28.00  63.00   0.50    0.10    --   58.93-126.00 -90.00   70
  8  \w     21.00  59.00   0.50    0.10    --   58.93-126.00   0.00   76
  9  \w     45.00  98.00   0.50    0.10    --   80.80-120.00  25.81  106
 10  \w     40.00  98.00   0.50    0.10    --   80.80-115.00  77.34  116
 11  \w     48.00  98.00   0.50    0.10    --   82.00-117.00 176.11  100
 12  \w     72.00  97.00   0.50    0.10    --   80.80-115.00  91.71   50
 13  \w     42.00  68.00   0.50    0.10    --   80.80-112.00-168.10   52
 14  \w    -84.00 -53.00   0.50    0.10    --  -60.27 -15.00  60.00   62
 15  \w   -115.00 -43.00   0.50    0.10    --  -75.18 -15.00 -30.00  144
 16  \w   -116.00 -85.00   0.50    0.10    --  -69.75 -15.00 -60.00   62
 17  \w    -70.00 -42.00   0.50    0.10    --  -69.75 -15.00 -60.00   56
 18  \w    -79.00 -43.00   0.50    0.10    --  -69.75 -15.00-150.00   72
 19  \w   -115.00 -82.00   0.50    0.10    --  -69.75 -15.00-150.00   66
 20  \w   -122.00 -43.00   0.50    0.10    --  -75.18 -15.00  60.00  158
 21  \w    -73.00 -47.00   0.50    0.10    --  -78.50 137.00  36.36   52
 22  \w    -58.00 -27.00   0.50    0.10    --  -69.75 126.00 120.00   62
 23  \w   -102.00 -76.00   0.50    0.10    --  -78.50 129.00 -59.19   52
 24  \w    -81.00 -55.00   0.50    0.10    --  -60.27 126.00-150.00   52
 25  \w    -53.00 -27.00   0.50    0.10    --  -60.27 126.00-150.00   52
 26  \w    -99.00 -43.00   0.50    0.10    --  -78.50 121.00-160.93  112
 27  \w   -100.00 -75.00   0.50    0.10    --  -78.50 125.00-113.32   50
 28  \w    -73.00 -48.00   0.50    0.10    --  -78.50 115.00 -96.90   50
 29  \w    -60.00 -35.00   0.50    0.10    --  -78.50 129.00 -59.19   50
 30  \w    -95.00 -69.00   0.50    0.10    --  -78.50 114.00-116.76   52
 31  \w    -60.00 -29.00   0.50    0.10    --  -69.75 126.00  30.00   62
 32  \w    -96.00 -44.00   0.50    0.10    --  -78.50 118.00  72.71  104
 33  \w    -60.00 -35.00   0.50    0.10    --  -78.50 125.00 179.77   50
 34  \w    -95.00 -47.00   0.50    0.10    --  -78.50 114.00 157.88   96
 35  \w    -84.00 -37.00   0.50    0.10    --  -75.18 112.00  30.00   94
 36  \w    -71.00 -42.00   0.50    0.10    --  -75.18 112.00 -30.00   58
 37  \w    -88.00 -37.00   0.50    0.10    --  -75.18 112.00-120.00  102
;
_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      0.0597288000
_diffrn_orient_matrix_UB_12      -0.0052840000
_diffrn_orient_matrix_UB_13      -0.0427324000
_diffrn_orient_matrix_UB_21      0.0430756000
_diffrn_orient_matrix_UB_22      -0.0600873000
_diffrn_orient_matrix_UB_23      0.0421301000
_diffrn_orient_matrix_UB_31      -0.0330012000
_diffrn_orient_matrix_UB_32      -0.0880807000
_diffrn_orient_matrix_UB_33      -0.0260731000
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38908
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.609
_diffrn_reflns_theta_min         3.756
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88878
_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    1.174
_exptl_crystal_description       block
_exptl_crystal_F_000             2424
_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          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         6335
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0549
_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^)+(0.1133P)^2^+2.0795P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5396
_reflns_number_total             6335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08526h2.cif
_cod_data_source_block           5TolPh
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1576382
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.890
_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              18810