Direct Arylation of Polycyclic Aromatic Hydrocarbons through Palladium Catalysis
Kenji Mochida; Katsuaki Kawasumi; Yasutomo Segawa; Kenichiro Itami; Journal of the American Chemical Society 133 (2011) 10716–10719; doi:10.1021/ja202975w

data_4106411
_publ_section_title
;
 Direct Arylation of Polycyclic Aromatic Hydrocarbons through Palladium
 Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10716
_journal_page_last               10719
_journal_paper_doi               10.1021/ja202975w
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C22 H14'
_chemical_formula_weight         278.33
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_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.33(2)
_cell_angle_beta                 77.27(2)
_cell_angle_gamma                75.35(2)
_cell_formula_units_Z            2
_cell_length_a                   5.739(3)
_cell_length_b                   10.225(6)
_cell_length_c                   12.543(7)
_cell_measurement_reflns_used    1418
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.5029
_cell_measurement_theta_min      3.3413
_cell_volume                     692.2(7)
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_collection       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_molecular_graphics    ORTEP-III
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Saturn70 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6990
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.34
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_correction_T_min  0.9925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       Block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1552
_reflns_number_gt                1630
_reflns_number_total             2425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja202975w_si_002_1.cif
_cod_data_source_block           2a
_cod_original_cell_volume        692.2(6)
_cod_database_code               4106411