Catalytic Enantioselective Synthesis of Axially Chiral Polycyclic Aromatic Hydrocarbons (PAHs) via Regioselective C-C Bond Activation of Biphenylenes.
Takano, Hideaki; Shiozawa, Natsumi; Imai, Yoshitane; Kanyiva, Kyalo Stephen; Shibata, Takanori; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b12205

data_4134235
_publ_section_title
;
 Catalytic Enantioselective Synthesis of Axially Chiral Polycyclic
 Aromatic Hydrocarbons (PAHs) via Regioselective C-C Bond Activation of
 Biphenylenes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12205
_journal_year                    2020
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C31 H27 Br'
_chemical_formula_sum            'C31 H27 Br'
_chemical_formula_weight         479.46
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                78.958(6)
_cell_angle_beta                 87.087(6)
_cell_angle_gamma                69.349(5)
_cell_formula_units_Z            2
_cell_length_a                   9.8221(4)
_cell_length_b                   9.8415(4)
_cell_length_c                   11.7712(4)
_cell_measurement_reflns_used    11551
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.83
_cell_volume                     1044.86(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11712
_diffrn_reflns_point_group_measured_fraction_full 0.811
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         3.827
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.797
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.26
_refine_diff_density_min         -0.72
_refine_ls_abs_structure_details
;
 Flack x determined using 2189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6167
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0708P)^2^+1.9342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1380
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.644
_reflns_Friedel_fraction_max     0.639
_reflns_number_gt                5887
_reflns_number_total             6167
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja9b12205_si_002.cif
_cod_data_source_block           Shiozawa_190130
_cod_database_code               4134235
_shelxl_version_number           2014/6
_shelx_res_checksum              29817
_shelx_hkl_checksum              75081