The forgotten borole: synthesis, properties and reactivity of a 1-boraindene.
Wieprecht, Nele; Krummenacher, Ivo; Wüst, Leonie; Michel, Maximilian; Fuchs, Sonja; Nees, Samuel; Härterich, Marcel; Braunschweig, Holger; Chemical science 15 (2024) 12496–12501; doi:10.1039/d4sc03817g

data_1572073
_publ_section_title
;
 The forgotten borole: synthesis, properties and reactivity of a
 1-boraindene.
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              12496
_journal_page_last               12501
_journal_paper_doi               10.1039/d4sc03817g
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C31 H24 B N'
_chemical_formula_sum            'C31 H24 B N'
_chemical_formula_weight         421.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-13
_audit_creation_method           'CIF-fill 1.4a (K.Radacki, 2005-23)'
_audit_update_record
;
2024-06-05 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.7320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.62580(10)
_cell_length_b                   13.3900(2)
_cell_length_c                   12.53570(10)
_cell_measurement_reflns_used    13763
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9130
_cell_measurement_theta_min      3.5490
_cell_volume                     2260.62(4)
_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 2018/2 (Sheldrick, 2018)''
_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 0.994
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -95.00 -23.00   0.50    0.10    --  -59.96 139.00-166.00  144
  2  \w   -105.00 -23.00   0.50    0.10    --  -69.45 139.00-166.00  164
  3  \w   -108.00 -30.00   0.50    0.10    --  -76.35 139.00-166.00  156
  4  \w    -97.00 -32.00   0.50    0.10    --  -78.00 114.00 -28.68  130
  5  \w   -100.00 -23.00   0.50    0.10    --  -69.45 132.00  17.00  154
  6  \w    -91.00 -18.00   0.50    0.10    --  -59.96 132.00  17.00  146
  7  \w   -106.00 -71.00   0.50    0.10    --  -58.00 -51.00 -36.17   70
  8  \w   -124.00 -94.00   0.50    0.10    --  -79.50 -64.00 -15.38   60
  9  \w   -125.00 -94.00   0.50    0.10    --  -79.50-119.00  75.31   62
 10  \w   -127.00 -92.00   0.50    0.10    --  -79.50 -54.00  93.83   70
 11  \w    -99.00 -64.00   0.50    0.10    --  -50.00 -47.00 152.39   70
 12  \w    -98.00 -63.00   0.50    0.10    --  -50.00 -52.00  11.77   70
 13  \w    -99.00 -64.00   0.50    0.10    --  -50.00 -47.00 -81.05   70
 14  \w     36.00 103.00   0.50    0.10    --   82.28-132.00 -51.00  134
 15  \w     36.00 108.00   0.50    0.10    --   82.28-139.00 133.00  144
 16  \w     39.00 107.00   0.50    0.10    --   85.25-138.00 164.21  136
 17  \w     29.00 107.00   0.50    0.10    --   71.14-139.00 133.00  156
 18  \w     81.00 107.00   0.50    0.10    --   85.25-137.00 109.96   52
 19  \w     51.00  99.00   0.50    0.10    --   85.25-121.00 -33.59   96
 20  \w     67.00  93.00   0.50    0.10    --   85.25-102.00  18.42   52
 21  \w     37.00  93.00   0.50    0.10    --   82.28-112.00 -60.00  112
 22  \w     49.00  75.00   0.50    0.10    --   85.25 -98.00-141.74   52
 23  \w     57.00  83.00   0.50    0.10    --   85.25-119.00-148.67   52
 24  \w     40.00  90.00   0.50    0.10    --   82.28 -95.00 -30.00  100
 25  \w     40.00  90.00   0.50    0.10    --   82.28 -95.00  30.00  100
 26  \w     40.00  90.00   0.50    0.10    --   82.28 -95.00  60.00  100
 27  \w     42.00  92.00   0.50    0.10    --   85.25 -98.00 171.00  100
 28  \w    106.00 131.00   0.50    0.10    --   85.25 120.00 131.75   50
 29  \w    100.00 131.00   0.50    0.10    --   85.25  56.00  66.42   62
 30  \w    101.00 126.00   0.50    0.10    --   85.25  48.00 175.20   50
 31  \w     46.00 133.00   0.50    0.10    --   82.28  15.00 150.00  174
 32  \w     46.00 133.00   0.50    0.10    --   82.28  15.00 -90.00  174
 33  \w    100.00 133.00   0.50    0.10    --   85.25  46.00-137.07   66
 34  \w    100.00 134.00   0.50    0.10    --   85.25  45.00-163.63   68
 35  \w     46.00 133.00   0.50    0.10    --   82.28  15.00-180.00  174
;
_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      -0.0260560000
_diffrn_orient_matrix_UB_12      -0.1100496000
_diffrn_orient_matrix_UB_13      0.0183331000
_diffrn_orient_matrix_UB_21      -0.0777082000
_diffrn_orient_matrix_UB_22      0.0335282000
_diffrn_orient_matrix_UB_23      0.0699782000
_diffrn_orient_matrix_UB_31      -0.0797562000
_diffrn_orient_matrix_UB_32      0.0032271000
_diffrn_orient_matrix_UB_33      -0.1010947000
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16399
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.131
_diffrn_reflns_theta_min         4.657
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59682
_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            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_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          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1247 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, 
 Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0493P)^2^+0.6109P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.572
_reflns_Friedel_fraction_full    0.606
_reflns_Friedel_fraction_max     0.562
_reflns_number_gt                3517
_reflns_number_total             3575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03817g2.cif
_cod_data_source_block           1-Py
_cod_depositor_comments
'Adding full bibliography for 1572071--1572079.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1572073
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.823
_shelx_estimated_absorpt_t_max   0.949
_shelx_res_checksum              13749