Gold-Catalyzed Stereoselective Synthesis of 9-Oxabicyclo[3.3.1]nona-4,7-dienes from Diverse 1-Oxo-4-oxy-5-ynes: A Viable Formal [4 + 2] Cycloaddition on an s-trans-Heterodiene Framework
Tse-Min Teng; Arindam Das; Deepak B. Huple; Rai-Shung Liu; Journal of the American Chemical Society 132 (2010) 12565–12567; doi:10.1021/ja106493h

data_4103045
_publ_section_title
;
 Gold-Catalyzed Stereoselective Synthesis of
 9-Oxabicyclo[3.3.1]nona-4,7-dienes from Diverse 1-Oxo-4-oxy-5-ynes: A
 Viable Formal [4 + 2] Cycloaddition on an s-trans-Heterodiene Framework
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12565
_journal_page_last               12567
_journal_paper_doi               10.1021/ja106493h
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_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                 107.107(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.8726(16)
_cell_length_b                   5.0504(3)
_cell_length_c                   21.1244(14)
_cell_measurement_reflns_used    988
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     2434.2(3)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker Saint'
_computing_molecular_graphics    'Bruker APEX2'
_computing_publication_material  'Bruker APEX2'
_computing_structure_refinement  'Shelxtl-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxtl-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4965
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Tabullar
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0844P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                1361
_reflns_number_total             2141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106493h_si_001.cif
_cod_data_source_block           090932_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4103045