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_1576376
_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         'C27 H21 B O'
_chemical_formula_sum            'C27 H21 B O'
_chemical_formula_weight         372.25
_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             2025-03-05
_audit_creation_method           'CIF-fill 1.5y (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                 106.7020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.1270(3)
_cell_length_b                   5.96440(10)
_cell_length_c                   33.0481(4)
_cell_measurement_reflns_used    10941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7440
_cell_measurement_theta_min      4.3680
_cell_volume                     3988.70(10)
_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 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
 
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    103.00 135.00   0.50    0.05    --   84.76  15.00-180.00   64
  2  \w     42.00  74.00   0.50    0.05    --   58.85  15.00  90.00   64
  3  \w     50.00 102.00   0.50    0.05    --   84.76  15.00 120.00  104
  4  \w     57.00 131.00   0.50    0.05    --   84.76  15.00 -30.00  148
  5  \w     49.00 113.00   0.50    0.05    --   84.76  15.00 -90.00  128
  6  \w     63.00 109.00   0.50    0.05    --   84.76  15.00-150.00   92
  7  \w     49.00  82.00   0.50    0.05    --   84.76  15.00-180.00   66
  8  \w     16.00  41.00   0.50    0.05    --   58.85 -95.00 -30.00   50
  9  \w     15.00  48.00   0.50    0.05    --   58.85-100.00-160.00   66
 10  \w     46.00  84.00   0.50    0.05    --   77.01-100.00-160.00   76
 11  \w     68.00  93.00   0.50    0.05    --   84.76-100.00-160.00   50
 12  \w     31.00  56.00   0.50    0.05    --   71.50-100.00-160.00   50
 13  \w     30.00  57.00   0.50    0.05    --   71.50 -95.00-180.00   54
 14  \w     16.00  43.00   0.50    0.05    --   58.85 -95.00-120.00   54
 15  \w     34.00  85.00   0.50    0.05    --   77.01 -95.00  30.00  102
 16  \w     25.00  57.00   0.50    0.05    --   58.85-126.00 120.00   64
 17  \w     42.00  69.00   0.50    0.05    --   84.76 -95.00 150.00   54
 18  \w     39.00  64.00   0.50    0.05    --   84.76-112.00 150.00   50
 19  \w     38.00  69.00   0.50    0.05    --   77.01 -95.00 120.00   62
 20  \w     67.00  92.00   0.50    0.05    --   84.76 -95.00 120.00   50
 21  \w     42.00  89.00   0.50    0.05    --   84.76 -95.00  60.00   94
 22  \w     43.00  70.00   0.50    0.05    --   84.76 -95.00   0.00   54
 23  \w     51.00  76.00   0.50    0.05    --   84.76 -95.00  30.00   50
 24  \w     42.00  92.00   0.50    0.05    --   84.76 -95.00 -30.00  100
 25  \w     44.00  92.00   0.50    0.05    --   84.76 -95.00 -60.00   96
 26  \w     44.00  92.00   0.50    0.05    --   84.76 -95.00-120.00   96
 27  \w     67.00  92.00   0.50    0.05    --   84.76 -95.00-150.00   50
 28  \w    -97.00 -45.00   0.50    0.05    --  -79.50 115.00-150.72  104
 29  \w    -64.00 -38.00   0.50    0.05    --  -76.45 112.00 -90.00   52
 30  \w    -42.00 -17.00   0.50    0.05    --  -60.43 100.00 -56.00   50
 31  \w    -52.00 -26.00   0.50    0.05    --  -69.92 100.00 -56.00   52
 32  \w    -79.00 -43.00   0.50    0.05    --  -76.45 100.00 -56.00   72
 33  \w    -92.00 -33.00   0.50    0.05    --  -76.45 112.00  30.00  118
 34  \w    -80.00 -32.00   0.50    0.05    --  -60.43 -15.00 120.00   96
 35  \w   -127.00 -42.00   0.50    0.05    --  -76.45 -15.00  60.00  170
 36  \w   -127.00 -44.00   0.50    0.05    --  -76.45 -15.00 -30.00  166
 37  \w   -119.00 -45.00   0.50    0.05    --  -69.92 -15.00-150.00  148
;
_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      0.0727196000
_diffrn_orient_matrix_UB_12      0.0760886000
_diffrn_orient_matrix_UB_13      0.0145577000
_diffrn_orient_matrix_UB_21      -0.0072071000
_diffrn_orient_matrix_UB_22      0.0573354000
_diffrn_orient_matrix_UB_23      0.0439097000
_diffrn_orient_matrix_UB_31      0.0212610000
_diffrn_orient_matrix_UB_32      -0.2401607000
_diffrn_orient_matrix_UB_33      0.0151168000
_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  0.0464
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            24901
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.192
_diffrn_reflns_theta_min         2.792
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72520
_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    1.240
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_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          0.580
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+1.9040P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3474
_reflns_number_total             4048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08526h2.cif
_cod_data_source_block           2Tol
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1576376
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.738
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              24395