Gold-Catalyzed [3+3]-Annulation of Azomethine Imines with Propargyl Esters
Nathan D. Shapiro; Yun Shi; F. Dean Toste; Journal of the American Chemical Society 131 (2009) 11654–11655; doi:10.1021/ja903863b

data_4104902
_publ_section_title
;
 Gold-Catalyzed [3+3]-Annulation of Azomethine Imines with Propargyl
 Esters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11654
_journal_page_last               11655
_journal_paper_doi               10.1021/ja903863b
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C29 H36 N2 O4'
_chemical_formula_sum            'C29 H36 N2 O4'
_chemical_formula_weight         476.60
_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                79.044(3)
_cell_angle_beta                 86.108(2)
_cell_angle_gamma                88.648(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4286(17)
_cell_length_b                   11.2717(19)
_cell_length_c                   11.714(2)
_cell_measurement_reflns_used    12784
_cell_measurement_temperature    152(2)
_cell_measurement_theta_max      50.664
_cell_measurement_theta_min      5.332
_cell_volume                     1348.7(4)
_computing_cell_refinement       'Bruker APEX2 v. 2009.3'
_computing_data_collection       'Bruker APEX2 v. 2009.3'
_computing_data_reduction        'Bruker APEX2 v. 2009.3'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      152(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       '\f and \w 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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12784
_diffrn_reflns_theta_full        25.43
_diffrn_reflns_theta_max         25.43
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.8494
_exptl_absorpt_correction_T_min  0.8075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0410
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1484
_reflns_number_gt                3291
_reflns_number_total             4941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903863b_si_002.cif
_cod_data_source_block           ns151
_cod_database_code               4104902