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_7133973
_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         'C38 H26 B2 Br2'
_chemical_formula_sum            'C38 H26 B2 Br2'
_chemical_formula_weight         664.03
_chemical_name_systematic        3Naph-Ph
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_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             2023-09-28
_audit_creation_method           'CIF-fill 1.4n (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                 90.3100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.80220(10)
_cell_length_b                   8.80000(10)
_cell_length_c                   33.2868(4)
_cell_measurement_reflns_used    18157
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0990
_cell_measurement_theta_min      4.6840
_cell_volume                     2871.26(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (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     43.00  90.00   0.50    0.30    --   82.26 -95.00  90.00   94
  2  \w     32.00  62.00   0.50    0.30    --   58.45 -95.00 150.00   60
  3  \w     47.00 133.00   0.50    0.30    --   82.26  15.00  60.00  172
  4  \w     65.00  90.00   0.50    0.30    --   82.26 -95.00   0.00   50
  5  \w     68.00  93.00   0.50    0.30    --   85.25 -97.00 146.55   50
  6  \w     52.00  90.00   0.50    0.30    --   82.26 -95.00 -90.00   76
  7  \w     41.00  90.00   0.50    0.30    --   82.26 -95.00-180.00   98
  8  \w     46.00 113.00   0.50    0.30    --   82.26  15.00-120.00  134
  9  \w     44.00  87.00   0.50    0.30    --   82.26 -95.00-120.00   86
 10  \w     51.00  89.00   0.50    0.30    --   82.26 -95.00 -30.00   76
 11  \w     48.00  88.00   0.50    0.30    --   82.26  15.00 150.00   80
 12  \w     44.00  92.00   0.50    0.30    --   85.25 -95.00-136.30   96
 13  \w    -51.00 -26.00   0.50    0.30    --  -69.54 126.00 -90.00   50
 14  \w   -119.00 -42.00   0.50    0.30    --  -76.37 -15.00  90.00  154
 15  \w     95.00 127.00   0.50    0.30    --   82.26  15.00 150.00   64
 16  \w     17.00  43.00   0.50    0.30    --   58.45 -95.00-150.00   52
 17  \w    -68.00 -38.00   0.50    0.30    --  -76.37 112.00-150.00   60
 18  \w    -71.00 -31.00   0.50    0.30    --  -76.37 112.00   0.00   80
 19  \w    103.00 130.00   0.50    0.30    --   82.26  15.00 -60.00   54
 20  \w     63.00  88.00   0.50    0.30    --   82.26 -95.00 120.00   50
 21  \w     22.00  48.00   0.50    0.30    --   58.45 -95.00  60.00   52
 22  \w     56.00  90.00   0.50    0.30    --   82.26 -95.00  60.00   68
 23  \w    -61.00 -33.00   0.50    0.30    --  -76.37 112.00 -60.00   56
 24  \w    -97.00 -44.00   0.50    0.30    --  -79.50 115.00-107.48  106
 25  \w    -76.00 -41.00   0.50    0.30    --  -76.37 -15.00   0.00   70
 26  \w    -97.00 -63.00   0.50    0.30    --  -79.50 116.00 -26.11   68
 27  \w    -91.00 -43.00   0.50    0.30    --  -76.37 112.00 150.00   96
 28  \w    -57.00 -32.00   0.50    0.30    --  -76.37 112.00 -90.00   50
 29  \w   -121.00 -56.00   0.50    0.30    --  -76.37 -15.00 -30.00  130
 30  \w     52.00  78.00   0.50    0.30    --   58.45  15.00   0.00   52
 31  \w    -66.00 -35.00   0.50    0.30    --  -76.37 112.00  60.00   62
 32  \w    -97.00 -35.00   0.50    0.30    --  -79.50 115.00  99.51  124
 33  \w     52.00 100.00   0.50    0.30    --   82.26  15.00 -60.00   96
 34  \w   -119.00 -44.00   0.50    0.30    --  -76.37 -15.00-150.00  150
 35  \w     83.00 109.00   0.50    0.30    --   58.45  15.00   0.00   52
 36  \w     22.00  56.00   0.50    0.30    --   58.45-126.00 -90.00   68
 37  \w     40.00  69.00   0.50    0.30    --   82.26-112.00  30.00   58
 38  \w     40.00  65.00   0.50    0.30    --   82.26 -95.00 -60.00   50
 39  \w     68.00  93.00   0.50    0.30    --   85.25 -98.00  45.51   50
;
_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      0.0610147000
_diffrn_orient_matrix_UB_12      0.1594001000
_diffrn_orient_matrix_UB_13      -0.0064683000
_diffrn_orient_matrix_UB_21      -0.1277195000
_diffrn_orient_matrix_UB_22      0.0464707000
_diffrn_orient_matrix_UB_23      -0.0242304000
_diffrn_orient_matrix_UB_31      -0.0682383000
_diffrn_orient_matrix_UB_32      0.0554640000
_diffrn_orient_matrix_UB_33      0.0389129000
_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  0.0438
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            35555
_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         74.940
_diffrn_reflns_theta_min         2.655
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    3.778
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021) 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 light green'
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       plate
_exptl_crystal_F_000             1336
_exptl_crystal_preparation
;
 Crystals were grown at 20 \%C from saturated solution in pentane. 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: pentane'
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0814P)^2^+3.3518P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5096
_reflns_number_total             5714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04433a3.cif
_cod_data_source_block           JoBo014_JoBo_a
_cod_depositor_comments
'Adding full bibliography for 7133971--7133976.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7133973
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.620
_shelx_estimated_absorpt_t_max   0.778
_shelx_res_checksum              95861
_shelx_hkl_checksum              38748