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_1576364
_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         'C20 H14 B Cl'
_chemical_formula_sum            'C20 H14 B Cl'
_chemical_formula_weight         300.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-05-03
_audit_creation_method           'CIF-fill 1.4x (K.Radacki, 2005-23)'
_audit_update_record
;
2025-11-03 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                106.123(4)
_cell_angle_beta                 98.243(4)
_cell_angle_gamma                91.855(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5358(5)
_cell_length_b                   9.1398(4)
_cell_length_c                   10.2329(4)
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0510
_cell_measurement_theta_min      4.5000
_cell_volume                     756.81(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 0.962
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     65.00  90.00   0.50    0.05    --   84.60 -95.00 -90.00   50
  2  \w     64.00  91.00   0.50    0.05    --   84.60 -95.00-150.00   54
  3  \w     38.00  64.00   0.50    0.05    --   71.24 -95.00   0.00   52
  4  \w     44.00 122.00   0.50    0.05    --   76.71  15.00 120.00  156
  5  \w     43.00  93.00   0.50    0.05    --   84.60-112.00  60.00  100
  6  \w     48.00 134.00   0.50    0.05    --   84.60  15.00  30.00  172
  7  \w     39.00  67.00   0.50    0.05    --   84.60-112.00 120.00   56
  8  \w     22.00  48.00   0.50    0.05    --   58.44 -95.00-150.00   52
  9  \w     41.00  75.00   0.50    0.05    --   76.71  15.00-150.00   68
 10  \w    -62.00 -22.00   0.50    0.05    --  -69.55 126.00 -90.00   80
 11  \w     21.00  62.00   0.50    0.05    --   58.44-126.00-150.00   82
 12  \w    -88.00 -34.00   0.50    0.05    --  -76.36 112.00  30.00  108
 13  \w     39.00  67.00   0.50    0.05    --   71.24 -95.00 -30.00   56
 14  \w     79.00 106.00   0.50    0.05    --   76.71  15.00-150.00   54
 15  \w     36.00  81.00   0.50    0.05    --   76.71 -95.00-150.00   90
 16  \w    -90.00 -53.00   0.50    0.05    --  -60.13 -15.00  60.00   74
 17  \w   -125.00 -42.00   0.50    0.05    --  -76.36 -15.00 150.00  166
 18  \w    -90.00 -32.00   0.50    0.05    --  -76.36 112.00-120.00  116
 19  \w   -118.00 -65.00   0.50    0.05    --  -69.55 -15.00  30.00  106
 20  \w     67.00  92.00   0.50    0.05    --   84.60 -95.00-120.00   50
 21  \w    -97.00 -35.00   0.50    0.05    --  -79.50 116.00  90.13  124
 22  \w     66.00  91.00   0.50    0.05    --   84.60 -95.00  90.00   50
 23  \w     16.00  48.00   0.50    0.05    --   58.44 -95.00  30.00   64
 24  \w     34.00  63.00   0.50    0.05    --   76.71-112.00 -90.00   58
 25  \w     41.00  68.00   0.50    0.05    --   76.71-112.00-180.00   54
 26  \w     17.00  43.00   0.50    0.05    --   58.44 -95.00 -60.00   52
 27  \w     60.00  91.00   0.50    0.05    --   84.60 -95.00-180.00   62
 28  \w     69.00  98.00   0.50    0.05    --   78.00-115.00  13.88   58
 29  \w     53.00 135.00   0.50    0.05    --   84.60  15.00 -60.00  164
 30  \w     62.00  90.00   0.50    0.05    --   84.60 -95.00 -60.00   56
;
_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      -0.1685013000
_diffrn_orient_matrix_UB_12      0.0550234000
_diffrn_orient_matrix_UB_13      -0.0159435000
_diffrn_orient_matrix_UB_21      0.0181566000
_diffrn_orient_matrix_UB_22      0.0147034000
_diffrn_orient_matrix_UB_23      -0.1435472000
_diffrn_orient_matrix_UB_31      -0.0687612000
_diffrn_orient_matrix_UB_32      -0.1664914000
_diffrn_orient_matrix_UB_33      -0.0658292000
_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  0.1202
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6615
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.252
_diffrn_reflns_theta_min         4.556
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    2.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22938
_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 dark red'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_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         0.553
_refine_diff_density_min         -1.019
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0876
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2390
_refine_ls_wR_factor_ref         0.2917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1926
_reflns_number_total             2816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08526h2.cif
_cod_data_source_block           1Cl
_cod_original_cell_volume        756.81(6)
_cod_database_code               1576364
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.586
_shelx_estimated_absorpt_t_max   0.799
_shelx_res_checksum              38480