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_1576379
_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         'C39 H31 B N2'
_chemical_formula_sum            'C39 H31 B N2'
_chemical_formula_weight         538.47
_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             2024-08-16
_audit_creation_method           'CIF-fill 1.5c (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                 96.206(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3787(2)
_cell_length_b                   22.2346(4)
_cell_length_c                   15.4814(3)
_cell_measurement_reflns_used    13417
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.3780
_cell_measurement_theta_min      3.4700
_cell_volume                     3209.44(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w   -106.00 -61.00   0.50    0.57    --  -60.27 -15.00-180.00   90
  2  \w   -108.00 -47.00   0.50    0.57    --  -69.75 -15.00 -90.00  122
  3  \w   -102.00 -58.00   0.50    0.57    --  -60.27 -15.00 -60.00   88
  4  \w   -119.00 -45.00   0.50    0.57    --  -75.18 -15.00 150.00  148
  5  \w   -117.00 -64.00   0.50    0.57    --  -75.18 -15.00  90.00  106
  6  \w   -109.00 -47.00   0.50    0.57    --  -69.75 -15.00  30.00  124
  7  \w   -103.00 -61.00   0.50    0.57    --  -69.75 -15.00 -30.00   84
  8  \w   -122.00 -44.00   0.50    0.57    --  -75.18 -15.00-120.00  156
  9  \w    -72.00 -44.00   0.50    0.57    --  -75.18 112.00   0.00   56
 10  \w    -71.00 -35.00   0.50    0.57    --  -78.50 135.00 119.60   72
 11  \w    -85.00 -27.00   0.50    0.57    --  -69.75 126.00  90.00  116
 12  \w    -97.00 -51.00   0.50    0.57    --  -78.50 118.00 162.08   92
 13  \w    -97.00 -66.00   0.50    0.57    --  -78.50 118.00 121.54   62
 14  \w    -96.00 -48.00   0.50    0.57    --  -78.50 116.00  19.78   96
 15  \w    -99.00 -35.00   0.50    0.57    --  -78.50 121.00 -64.10  128
 16  \w    -64.00 -39.00   0.50    0.57    --  -78.50 129.00-167.38   50
 17  \w    -59.00 -26.00   0.50    0.57    --  -69.75 126.00-150.00   66
 18  \w    -71.00 -37.00   0.50    0.57    --  -75.18 112.00-180.00   68
 19  \w    -82.00 -34.00   0.50    0.57    --  -75.18 112.00-120.00   96
 20  \w    -79.00 -53.00   0.50    0.57    --  -75.18 112.00 -90.00   52
 21  \w    -96.00 -51.00   0.50    0.57    --  -78.50 116.00 -82.20   90
 22  \w    -68.00 -42.00   0.50    0.57    --  -75.18 112.00 -60.00   52
 23  \w    -96.00 -38.00   0.50    0.57    --  -78.50 116.00  81.27  116
 24  \w    -63.00 -38.00   0.50    0.57    --  -75.18 112.00  60.00   50
 25  \w    -88.00 -45.00   0.50    0.57    --  -75.18 112.00 120.00   86
 26  \w     60.00  98.00   0.50    0.57    --   76.88  15.00 150.00   76
 27  \w     41.00 100.00   0.50    0.57    --   80.80-124.00 120.13  118
 28  \w     21.00  55.00   0.50    0.57    --   58.63-126.00  90.00   68
 29  \w     47.00  98.00   0.50    0.57    --   80.80-118.00  51.90  102
 30  \w     25.00  66.00   0.50    0.57    --   58.63-126.00   0.00   82
 31  \w     53.00  98.00   0.50    0.57    --   80.80-115.00 -82.49   90
 32  \w     23.00  62.00   0.50    0.57    --   58.63-126.00-120.00   78
 33  \w     45.00 119.00   0.50    0.57    --   76.88  15.00  90.00  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      -0.0265472000
_diffrn_orient_matrix_UB_12      0.0459777000
_diffrn_orient_matrix_UB_13      -0.0744531000
_diffrn_orient_matrix_UB_21      -0.1322389000
_diffrn_orient_matrix_UB_22      -0.0361426000
_diffrn_orient_matrix_UB_23      -0.0382569000
_diffrn_orient_matrix_UB_31      -0.0954154000
_diffrn_orient_matrix_UB_32      0.0371139000
_diffrn_orient_matrix_UB_33      0.0549639000
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            40448
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.293
_diffrn_reflns_theta_min         3.493
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69819
_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 yellow'
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_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          0.180
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         6241
_refine_ls_number_restraints     785
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+2.2167P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5091
_reflns_number_total             6241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08526h2.cif
_cod_data_source_block           8Tol
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1576379
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              13086
_shelx_fab_checksum              95270