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_4106413
_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            'C30 H18'
_chemical_formula_weight         378.44
_space_group_IT_number           2
_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                85.547(12)
_cell_angle_beta                 85.134(11)
_cell_angle_gamma                78.235(12)
_cell_formula_units_Z            2
_cell_length_a                   3.9020(15)
_cell_length_b                   12.153(5)
_cell_length_c                   19.400(8)
_cell_measurement_reflns_used    1825
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      25.3295
_cell_measurement_theta_min      3.1676
_cell_volume                     895.7(6)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6035
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       Chip
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0603P)^2^+0.0716P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                2031
_reflns_number_total             3107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja202975w_si_002_3.cif
_cod_data_source_block           8
_cod_database_code               4106413