Synthesis of the Phenanthrene and Cyclohepta[a]naphthalene Skeletons via Gold(I)-Catalyzed Intramolecular Cyclization of Unactivated Cyclic 5-(2-Arylethyl)-1,3-dienes
Ming-Chang P. Yeh; Ming-Nan Lin; Yi-Shiang Chou; Tern-Chi Lin; Li-Yu Tseng; Journal of Organic Chemistry 76 (2011) 4027–4033; doi:10.1021/jo200445p

data_4026312
_publ_section_title
;
 Synthesis of the Phenanthrene and Cyclohepta[a]naphthalene Skeletons via
 Gold(I)-Catalyzed Intramolecular Cyclization of Unactivated Cyclic
 5-(2-Arylethyl)-1,3-dienes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4027
_journal_page_last               4033
_journal_paper_doi               10.1021/jo200445p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C22 H22 O4'
_chemical_formula_sum            'C22 H22 O4'
_chemical_formula_weight         350.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 96.5800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.86000(10)
_cell_length_b                   17.5610(3)
_cell_length_c                   11.8540(2)
_cell_measurement_reflns_used    16610
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.037
_cell_volume                     1832.22(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 19'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17401
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.3179
_exptl_absorpt_correction_T_min  0.7154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0792P)^2^+0.5030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                2604
_reflns_number_total             3349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200445p_si_003_2.cif
_cod_data_source_block           7238
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026312