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_1576375
_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         'C26 H19 B O'
_chemical_formula_sum            'C26 H19 B O'
_chemical_formula_weight         358.22
_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             2023-07-03
_audit_creation_method           'CIF-fill 1.4k (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                 90.730(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2253(3)
_cell_length_b                   9.1892(3)
_cell_length_c                   15.5388(4)
_cell_measurement_reflns_used    7409
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9180
_cell_measurement_theta_min      4.3430
_cell_volume                     1888.28(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.63a (Rigaku OD, 2023)'
_computing_data_collection
;
 CrysAlisPro system (CCD 42.94a 64-bit (release 21-06-2023))
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     43.00  69.00   0.50    0.12    --   84.34 -95.00 120.00   52
  2  \w     17.00  55.00   0.50    0.12    --   58.45-117.00 -38.00   76
  3  \w     37.00  84.00   0.50    0.12    --   76.32 -95.00  30.00   94
  4  \w     31.00  58.00   0.50    0.12    --   58.45 -95.00  30.00   54
  5  \w   -126.00 -42.00   0.50    0.12    --  -76.37 -15.00 -60.00  168
  6  \w     36.00  98.00   0.50    0.12    --   76.32-117.00 -38.00  124
  7  \w    -92.00 -37.00   0.50    0.12    --  -76.37 112.00-150.00  110
  8  \w     44.00  69.00   0.50    0.12    --   84.34-117.00 -38.00   50
  9  \w     39.00 106.00   0.50    0.12    --   58.45  15.00-180.00  134
 10  \w     62.00  90.00   0.50    0.12    --   84.34 -95.00   0.00   56
 11  \w     80.00 125.00   0.50    0.12    --   76.32  15.00 -60.00   90
 12  \w     27.00  52.00   0.50    0.12    --   58.45 -95.00-120.00   50
 13  \w     45.00  92.00   0.50    0.12    --   84.34 -95.00  60.00   94
 14  \w    -55.00 -26.00   0.50    0.12    --  -60.36 117.00  48.00   58
 15  \w     66.00  92.00   0.50    0.12    --   84.34 -95.00 -30.00   52
 16  \w    -85.00 -60.00   0.50    0.12    --  -76.37 117.00  48.00   50
 17  \w     34.00  59.00   0.50    0.12    --   71.26-117.00 -38.00   50
 18  \w     66.00  92.00   0.50    0.12    --   84.34 -95.00  30.00   52
 19  \w    -57.00 -31.00   0.50    0.12    --  -76.37 117.00  48.00   52
 20  \w    -82.00 -57.00   0.50    0.12    --  -69.85 117.00  48.00   50
 21  \w     42.00  81.00   0.50    0.12    --   58.45  15.00  60.00   78
 22  \w     51.00 134.00   0.50    0.12    --   84.34  15.00  90.00  166
 23  \w     57.00  92.00   0.50    0.12    --   84.34 -95.00 -60.00   70
 24  \w     49.00  75.00   0.50    0.12    --   76.32  15.00 -60.00   52
 25  \w     36.00  62.00   0.50    0.12    --   76.32 -95.00 150.00   52
;
_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      0.0017607000
_diffrn_orient_matrix_UB_12      0.1652865000
_diffrn_orient_matrix_UB_13      -0.0165427000
_diffrn_orient_matrix_UB_21      0.0955729000
_diffrn_orient_matrix_UB_22      0.0143123000
_diffrn_orient_matrix_UB_23      0.0571345000
_diffrn_orient_matrix_UB_31      0.0665241000
_diffrn_orient_matrix_UB_32      -0.0244758000
_diffrn_orient_matrix_UB_33      -0.0793299000
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14109
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.719
_diffrn_reflns_theta_min         4.363
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.863
_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            red
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_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          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0672P)^2^+0.4659P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2952
_reflns_number_total             3684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08526h2.cif
_cod_data_source_block           2Ph
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1576375
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.935
_shelx_estimated_absorpt_t_max   0.956
_shelx_res_checksum              83520