Pd-Catalyzed Cascade Crossover Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes
Jian Zhao; Kazuaki Oniwa; Naoki Asao; Yoshinori Yamamoto; Tienan Jin; Journal of the American Chemical Society 135 (2013) 10222–10225; doi:10.1021/ja403382d

data_4120103
_publ_contact_author_email       tjin@m.tohoku.ac.jp
_publ_contact_author_name        'Tienan Jin'
_publ_contact_author_phone       81-22-217-6177
_publ_section_title
;
 Pd-Catalyzed Cascade Crossover Annulation of o-Alkynylarylhalides and
 Diarylacetylenes Leading to Dibenzo[a,e]pentalenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10222
_journal_page_last               10225
_journal_paper_doi               10.1021/ja403382d
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C30 H20 O'
_chemical_formula_sum            'C30 H20 O'
_chemical_formula_weight         396.46
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.5545(2)
_cell_length_b                   50.5515(15)
_cell_length_c                   10.7005(4)
_cell_measurement_temperature    300
_cell_volume                     4086.4(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_source         'sealed x-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       65
_diffrn_reflns_limit_k_min       -59
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            40823
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (RIGAKU, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       platlet
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          1.2
_exptl_crystal_size_mid          1.0
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0505P)^2^+1.4950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                3021
_reflns_number_total             4653
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja403382d_si_002.cif
_cod_data_source_block           ydkr
_cod_database_code               4120103