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_1576384
_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         'C38 H29 B N2'
_chemical_formula_sum            'C38 H29 B N2'
_chemical_formula_weight         524.44
_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             2024-05-07
_audit_creation_method           'CIF-fill 1.4y (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                 99.7420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.30010(10)
_cell_length_b                   14.8242(2)
_cell_length_c                   23.1387(3)
_cell_measurement_reflns_used    13424
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.1200
_cell_measurement_theta_min      3.5340
_cell_volume                     3144.05(7)
_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 0.969
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     60.00 123.00   0.50    0.65    --   84.60  15.00  90.00  126
  2  \w     53.00 121.00   0.50    0.65    --   84.60  15.00  30.00  136
  3  \w     93.00 135.00   0.50    0.65    --   84.60  15.00 -60.00   84
  4  \w     58.00  83.00   0.50    0.65    --   84.60  15.00 -60.00   50
  5  \w     66.00  91.00   0.50    0.65    --   84.60 -95.00-150.00   50
  6  \w     39.00  64.00   0.50    0.65    --   84.60-112.00-150.00   50
  7  \w     43.00  93.00   0.50    0.65    --   76.71-112.00-180.00  100
  8  \w     39.00  66.00   0.50    0.65    --   76.71 -95.00-150.00   54
  9  \w     41.00  93.00   0.50    0.65    --   84.60-112.00 -90.00  104
 10  \w     16.00  47.00   0.50    0.65    --   58.74 -95.00 -30.00   62
 11  \w     28.00  64.00   0.50    0.65    --   58.74-126.00  30.00   72
 12  \w     61.00  91.00   0.50    0.65    --   84.60 -95.00 -30.00   60
 13  \w     34.00  68.00   0.50    0.65    --   76.71 -95.00  90.00   68
 14  \w     34.00  74.00   0.50    0.65    --   76.71 -95.00 120.00   80
 15  \w     18.00  50.00   0.50    0.65    --   58.74 -95.00 150.00   64
 16  \w     65.00  91.00   0.50    0.65    --   84.60 -95.00 150.00   52
 17  \w     32.00  80.00   0.50    0.65    --   58.74-126.00 150.00   96
 18  \w     22.00  52.00   0.50    0.65    --   58.74 -95.00  60.00   60
 19  \w     46.00  92.00   0.50    0.65    --   84.60 -95.00  60.00   92
 20  \w     42.00  92.00   0.50    0.65    --   84.60 -95.00  30.00  100
 21  \w     50.00  92.00   0.50    0.65    --   84.60 -95.00   0.00   84
 22  \w     67.00  92.00   0.50    0.65    --   84.60 -95.00 120.00   50
 23  \w     46.00  92.00   0.50    0.65    --   84.60 -95.00 -60.00   92
 24  \w     51.00  92.00   0.50    0.65    --   84.60 -95.00 -90.00   82
 25  \w     16.00  41.00   0.50    0.65    --   58.74 -95.00-150.00   50
 26  \w     65.00  91.00   0.50    0.65    --   84.60 -95.00-180.00   52
 27  \w    -61.00 -29.00   0.50    0.65    --  -60.33 126.00-180.00   64
 28  \w    -93.00 -35.00   0.50    0.65    --  -79.50 106.00-111.22  116
 29  \w    -97.00 -41.00   0.50    0.65    --  -79.50 115.00  -1.32  112
 30  \w    -97.00 -33.00   0.50    0.65    --  -79.50 117.00 -68.75  128
 31  \w    -80.00 -36.00   0.50    0.65    --  -60.33 -15.00 -60.00   88
 32  \w   -127.00 -40.00   0.50    0.65    --  -76.36 -15.00-150.00  174
 33  \w   -125.00 -42.00   0.50    0.65    --  -76.36 -15.00  30.00  166
 34  \w    -70.00 -38.00   0.50    0.65    --  -69.86 -15.00  90.00   64
 35  \w   -111.00 -72.00   0.50    0.65    --  -69.86 -15.00  90.00   78
 36  \w   -126.00 -41.00   0.50    0.65    --  -76.36 -15.00 120.00  170
;
_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      0.0538743000
_diffrn_orient_matrix_UB_12      -0.0799486000
_diffrn_orient_matrix_UB_13      0.0404386000
_diffrn_orient_matrix_UB_21      -0.1583764000
_diffrn_orient_matrix_UB_22      -0.0331644000
_diffrn_orient_matrix_UB_23      -0.0040238000
_diffrn_orient_matrix_UB_31      0.0165015000
_diffrn_orient_matrix_UB_32      -0.0572956000
_diffrn_orient_matrix_UB_33      -0.0540492000
_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  0.0523
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            40406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.665
_diffrn_reflns_theta_min         3.556
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43092
_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    1.108
_exptl_crystal_description       needle
_exptl_crystal_F_000             1104
_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          0.280
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         6321
_refine_ls_number_restraints     2337
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0739P)^2^+1.1468P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1497
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4959
_reflns_number_total             6321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08526h2.cif
_cod_data_source_block           8Ph
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1576384
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.876
_shelx_estimated_absorpt_t_max   0.948
_shelx_res_checksum              14787
_shelx_fab_checksum              15725