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_4026316
_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         'C20 H24 O6'
_chemical_formula_sum            'C20 H24 O6'
_chemical_formula_weight         360.39
_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                65.820(5)
_cell_angle_beta                 89.730(4)
_cell_angle_gamma                73.515(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5409(5)
_cell_length_b                   9.9028(7)
_cell_length_c                   12.1158(9)
_cell_measurement_reflns_used    8010
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.037
_cell_volume                     889.09(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_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    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0819
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_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            6567
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.0326
_exptl_absorpt_correction_T_min  0.9246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.046(10)
_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   1.034
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0832
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1084P)^2^+0.7482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2468
_reflns_number_gt                1867
_reflns_number_total             3221
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200445p_si_003_6.cif
_cod_data_source_block           8620
_cod_original_cell_volume        889.09(10)
_cod_database_code               4026316