One-step selective synthesis of doubly and triply fused chiral boroloborole derivatives.
Bohlen, Josina L.; Wieprecht, Nele; Arrowsmith, Merle; Häfner, Alena; Neder, Marco; Braunschweig, Holger; Chemical communications (Cambridge, England) 60 (2024) 14782–14785; doi:10.1039/d4cc04433a

data_7133976
_publ_section_title
;
 One-step selective synthesis of doubly and triply fused chiral
 boroloborole derivatives.
;
_journal_issue                   99
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14782
_journal_page_last               14785
_journal_paper_doi               10.1039/d4cc04433a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C46 H32 B2, C6 H6'
_chemical_formula_sum            'C52 H38 B2'
_chemical_formula_weight         684.44
_chemical_name_systematic        4Bz-BzPh
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-06-14
_audit_creation_method           'CIF-fill 1.5c (K.Radacki, 2005-23)'
_audit_update_record
;
2024-08-23 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.95130(10)
_cell_length_b                   15.16980(10)
_cell_length_c                   23.25820(10)
_cell_measurement_reflns_used    56480
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7370
_cell_measurement_theta_min      3.7930
_cell_volume                     7392.08(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-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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 0.991
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     48.00  92.00   0.50    0.13    --   84.60  15.00 -90.00   88
  2  \w    -97.00 -32.00   0.50    0.13    --  -78.00 114.00 137.32  130
  3  \w    -60.00 -26.00   0.50    0.13    --  -69.86 126.00-180.00   68
  4  \w    -60.00 -25.00   0.50    0.13    --  -69.86 126.00 120.00   70
  5  \w    110.00 135.00   0.50    0.13    --   84.60  15.00 -90.00   50
  6  \w   -107.00 -70.00   0.50    0.13    --  -60.33 -15.00  90.00   74
  7  \w    -58.00 -33.00   0.50    0.13    --  -60.33 -15.00  90.00   50
  8  \w     39.00  64.00   0.50    0.13    --   84.60-112.00  90.00   50
  9  \w     58.00  89.00   0.50    0.13    --   84.60 -95.00-120.00   62
 10  \w     67.00  92.00   0.50    0.13    --   84.60 -95.00 150.00   50
 11  \w   -127.00 -40.00   0.50    0.13    --  -76.36 -15.00-120.00  174
 12  \w     46.00  91.00   0.50    0.13    --   84.60 -95.00 -30.00   90
 13  \w    -56.00 -22.00   0.50    0.13    --  -69.86 126.00 -60.00   68
 14  \w     18.00  45.00   0.50    0.13    --   58.74 -95.00 -60.00   54
 15  \w     53.00  91.00   0.50    0.13    --   84.60 -95.00   0.00   76
 16  \w     66.00  91.00   0.50    0.13    --   84.60 -95.00 -90.00   50
 17  \w     56.00 106.00   0.50    0.13    --   58.74  15.00 -90.00  100
 18  \w     66.00  91.00   0.50    0.13    --   84.60 -95.00  90.00   50
 19  \w    -64.00 -31.00   0.50    0.13    --  -76.36 112.00  90.00   66
 20  \w     21.00  48.00   0.50    0.13    --   58.74 -95.00 -30.00   54
 21  \w     66.00  91.00   0.50    0.13    --   84.60 -95.00  60.00   50
 22  \w    -97.00 -34.00   0.50    0.13    --  -79.50 115.00  47.97  126
 23  \w     66.00  92.00   0.50    0.13    --   84.60 -95.00 -60.00   52
 24  \w     44.00  72.00   0.50    0.13    --   58.74  15.00   0.00   56
 25  \w     50.00 135.00   0.50    0.13    --   84.60  15.00  90.00  170
 26  \w   -111.00 -59.00   0.50    0.13    --  -60.33 -15.00  30.00  104
 27  \w   -126.00 -42.00   0.50    0.13    --  -76.36 -15.00 -30.00  168
 28  \w    -79.00 -31.00   0.50    0.13    --  -76.36 112.00-180.00   96
 29  \w    -64.00 -24.00   0.50    0.13    --  -60.33 126.00  30.00   80
 30  \w     44.00  90.00   0.50    0.13    --   84.60 -95.00 120.00   92
 31  \w     41.00  93.00   0.50    0.13    --   84.60-112.00 -30.00  104
 32  \w     35.00  92.00   0.50    0.13    --   76.71-112.00 -60.00  114
 33  \w     34.00  59.00   0.50    0.13    --   76.71 -95.00-180.00   50
 34  \w     66.00  92.00   0.50    0.13    --   84.60 -95.00-150.00   52
 35  \w     40.00  84.00   0.50    0.13    --   76.71 -95.00   0.00   88
 36  \w     34.00  59.00   0.50    0.13    --   76.71 -95.00 -90.00   50
 37  \w     63.00  92.00   0.50    0.13    --   84.60 -95.00  30.00   58
 38  \w     22.00  51.00   0.50    0.13    --   58.74 -95.00   0.00   58
 39  \w     37.00  68.00   0.50    0.13    --   76.71 -95.00  30.00   62
 40  \w     48.00 135.00   0.50    0.13    --   84.60  15.00-180.00  174
 41  \w     67.00  92.00   0.50    0.13    --   84.60 -95.00-180.00   50
 42  \w     24.00  58.00   0.50    0.13    --   71.44-126.00-180.00   68
;
_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      0.0664195000
_diffrn_orient_matrix_UB_12      0.0174184000
_diffrn_orient_matrix_UB_13      0.0260450000
_diffrn_orient_matrix_UB_21      -0.0297322000
_diffrn_orient_matrix_UB_22      0.0657267000
_diffrn_orient_matrix_UB_23      0.0428142000
_diffrn_orient_matrix_UB_31      -0.0105220000
_diffrn_orient_matrix_UB_32      -0.0754353000
_diffrn_orient_matrix_UB_33      0.0433147000
_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  0.0310
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            101208
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.986
_diffrn_reflns_theta_min         3.801
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72238
_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    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             2880
_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_recrystallization_method 'Re-crystallisation from solvent: C6H6'
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         7542
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0425P)^2^+2.4536P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6691
_reflns_number_total             7542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04433a3.cif
_cod_data_source_block           NeWi019_NeWi_a
_cod_depositor_comments
'Adding full bibliography for 7133971--7133976.cif.'
_cod_database_code               7133976
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.873
_shelx_estimated_absorpt_t_max   0.945
_shelx_res_checksum              45680
_shelx_hkl_checksum              86801