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_1576366
_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 S'
_chemical_formula_sum            'C26 H19 B S'
_chemical_formula_weight         374.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-10-10
_audit_creation_method           'CIF-fill 1.4n (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                 109.636(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.17820(10)
_cell_length_b                   21.3880(2)
_cell_length_c                   9.63210(10)
_cell_measurement_reflns_used    23436
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7470
_cell_measurement_theta_min      4.1030
_cell_volume                     1974.89(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.89a (Rigaku OD, 2023)'
_computing_data_collection
;
 CrysAlisPro system (CCD 42.94a 64-bit (release 21-06-2023))
;
_computing_data_reduction        'CrysAlisPro 1.171.43.89a (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 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -92.00 -55.00   0.50    0.05    --  -42.00 -45.00 103.13   74
  2  \w   -111.00 -76.00   0.50    0.05    --  -62.00 -50.00 -74.14   70
  3  \w   -120.00 -83.00   0.50    0.05    --  -70.00 -45.00-104.94   74
  4  \w   -122.00 -87.00   0.50    0.05    --  -74.00 -52.00-125.91   70
  5  \w   -124.00 -86.00   0.50    0.05    --  -74.00 -42.00 -22.04   76
  6  \w   -102.00 -67.00   0.50    0.05    --  -54.00 -52.00-156.56   70
  7  \w     16.00  66.00   0.50    0.05    --   58.45 -95.00 -60.00  100
  8  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00 -30.00  100
  9  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00 -60.00  100
 10  \w    -92.00 -31.00   0.50    0.05    --  -76.37 112.00 150.00  122
 11  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00-120.00  100
 12  \w   -127.00 -40.00   0.50    0.05    --  -76.37 -15.00  30.00  174
 13  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00-180.00  100
 14  \w    -45.00 -19.00   0.50    0.05    --  -14.00 133.00  35.20   52
 15  \w   -122.00 -87.00   0.50    0.05    --  -74.00 -52.00 142.97   70
 16  \w     40.00 127.00   0.50    0.05    --   76.32  15.00   0.00  174
 17  \w   -102.00 -67.00   0.50    0.05    --  -54.00 -52.00  76.47   70
 18  \w   -106.00 -71.00   0.50    0.05    --  -58.00 -52.00 168.37   70
 19  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -52.00 130.47   70
 20  \w   -120.00 -83.00   0.50    0.05    --  -70.00 -46.00 -32.24   74
 21  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -52.00  20.54   70
 22  \w   -107.00 -72.00   0.50    0.05    --  -58.00 -50.00  42.83   70
 23  \w   -126.00 -92.00   0.50    0.05    --  -79.50 -57.00  10.97   68
 24  \w   -111.00 -76.00   0.50    0.05    --  -62.00 -48.00   4.13   70
 25  \w   -126.00 -92.00   0.50    0.05    --  -79.50-123.00  89.90   68
 26  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00  90.00  100
 27  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00 150.00  100
 28  \w   -124.00 -86.00   0.50    0.05    --  -74.00 -42.00 -92.96   76
 29  \w    -87.00 -52.00   0.50    0.05    --  -38.00 -47.00   6.65   70
 30  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00  60.00  100
 31  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00 120.00  100
 32  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00   0.00  100
 33  \w     30.00  60.00   0.50    0.05    --   18.00  59.00  95.18   60
 34  \w     30.00  56.00   0.50    0.05    --   18.00  60.00 -72.70   52
 35  \w     48.00 103.00   0.50    0.05    --   84.34  15.00 -60.00  110
 36  \w   -126.00 -93.00   0.50    0.05    --  -79.50-121.00 108.60   66
 37  \w    -88.00 -14.00   0.50    0.05    --  -60.36 126.00   0.00  148
 38  \w     34.00  60.00   0.50    0.05    --   22.00  58.00 -32.46   52
 39  \w     34.00  84.00   0.50    0.05    --   76.32 -95.00 -90.00  100
 40  \w     30.00  56.00   0.50    0.05    --   18.00  60.00  12.99   52
 41  \w     34.00  84.00   0.50    0.05    --   76.32 -95.00  60.00  100
 42  \w     30.00  56.00   0.50    0.05    --   18.00  60.00-117.21   52
 43  \w     31.00  93.00   0.50    0.05    --   76.32-112.00-120.00  124
 44  \w     31.00  93.00   0.50    0.05    --   76.32-112.00 150.00  124
 45  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00 -90.00  100
 46  \w     39.00  93.00   0.50    0.05    --   84.34-112.00 120.00  108
 47  \w     34.00  60.00   0.50    0.05    --   22.00  59.00-160.56   52
 48  \w     42.00  92.00   0.50    0.05    --   84.34 -95.00  30.00  100
 49  \w    -92.00 -31.00   0.50    0.05    --  -76.37 112.00 -90.00  122
 50  \w   -131.00 -65.00   0.50    0.05    --  -79.50 -19.00 147.75  132
 51  \w    -92.00 -31.00   0.50    0.05    --  -76.37 112.00 -30.00  122
;
_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      -0.0699286000
_diffrn_orient_matrix_UB_12      -0.0551153000
_diffrn_orient_matrix_UB_13      -0.1007073000
_diffrn_orient_matrix_UB_21      0.1435841000
_diffrn_orient_matrix_UB_22      -0.0216968000
_diffrn_orient_matrix_UB_23      -0.0023717000
_diffrn_orient_matrix_UB_31      0.0180468000
_diffrn_orient_matrix_UB_32      -0.0410190000
_diffrn_orient_matrix_UB_33      0.1366274000
_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  0.0366
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            36367
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.697
_diffrn_reflns_theta_min         4.134
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    1.491
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.43.89a (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            'clear pale yellow'
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_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          0.380
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.047
_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     253
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0560P)^2^+0.8747P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3591
_reflns_number_total             3975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08526h2.cif
_cod_data_source_block           3bPh
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1576366
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.601
_shelx_estimated_absorpt_t_max   0.903
_shelx_res_checksum              73302