Au(I)-Catalyzed Cycloisomerization Reaction of Amide- or Ester-Tethered 1,6-Enynes to Bicyclo[3.2.0]hept-6-en-2-ones
Young Tak Lee; Youn Kyung Kang; Young Keun Chung; Journal of Organic Chemistry 74 (2009) 7922–7934; doi:10.1021/jo901771p

data_4024933
_publ_section_title
;
Au(I)-Catalyzed Cycloisomerization Reaction of Amide- or Ester-Tethered
1,6-Enynes to Bicyclo[3.2.0]hept-6-en-2-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7922
_journal_page_last               7934
_journal_paper_doi               10.1021/jo901771p
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C20.5 H20 Cl N O3 S'
_chemical_formula_weight         389.898
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 110.146(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.8036(7)
_cell_length_b                   6.1821(2)
_cell_length_c                   24.8527(8)
_cell_measurement_reflns_used    4481
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     3866.2(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    ORTEP32
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K-alpha'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7514
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  0.9377
_exptl_absorpt_correction_T_min  0.9085
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Blessing, R. H. Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0524P)^2^+2.2270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                2973
_reflns_number_total             4360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901771p_si_003.cif
_cod_data_source_block           14
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C20.50 H20 Cl N O3 S'
_cod_database_code               4024933