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_4104901
_publ_section_title
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 Gold-Catalyzed [3+3]-Annulation of Azomethine Imines with Propargyl
 Esters
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_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_sum            'C28 H27 N2 O3'
_chemical_formula_weight         439.52
_chemical_name_common            12-060B
_chemical_name_systematic
;
 toste02
;
_space_group.centring_type       P
_space_group_IT_number           2
_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                65.821(3)
_cell_angle_beta                 79.428(4)
_cell_angle_gamma                85.202(4)
_cell_formula_units_Z            2
_cell_length_a                   6.539(2)
_cell_length_b                   13.164(4)
_cell_length_c                   14.645(4)
_cell_measurement_reflns_used    1782
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      22.85
_cell_measurement_theta_min      2.87
_cell_volume                     1130.5(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_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  0.1367
_diffrn_reflns_av_sigmaI/netI    0.1670
_diffrn_refln_scan_rate          60
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13356
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.9900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       plate
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1928
_refine_ls_R_factor_gt           0.0822
_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^)+(0.0675P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1907
_reflns_number_gt                1895
_reflns_number_total             4093
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903863b_si_001.cif
_cod_data_source_block           toste02
_cod_depositor_comments
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The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
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_cod_database_code               4104901