Highly regioselective Au(I)-catalyzed hydroamination of ynamides and propiolic acid derivatives with anilines.
Kramer, Søren; Dooleweerdt, Karin; Lindhardt, Anders Thyboe; Rottländer, Mario; Skrydstrup, Troels; Organic letters 11 (2009) 4208–4211; doi:10.1021/ol901565p

data_1504119
_publ_section_title
;
 Highly regioselective Au(I)-catalyzed hydroamination of ynamides and
 propiolic acid derivatives with anilines.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4208
_journal_page_last               4211
_journal_paper_doi               10.1021/ol901565p
_journal_volume                  11
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H15 I1 N2 O2'
_chemical_formula_sum            'C17 H15 I N2 O2'
_chemical_formula_weight         406.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-04-29T11:25:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.968(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8625(3)
_cell_length_b                   10.7999(4)
_cell_length_c                   18.3965(8)
_cell_measurement_reflns_used    9091
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.231
_cell_measurement_theta_min      2.214
_cell_measurement_wavelength     0.71073
_cell_volume                     1561.90(11)
_computing_cell_refinement       'Saint+ v7.60A (Bruker-Nonius, 2009)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2009)'
_computing_data_reduction        'Saint+ v7.60A (Bruker-Nonius, 2009)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 12.00
_diffrn_detector_type            'APEX2 charged-coupled device'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method
;
            Narrow slices collected using \f- and \w-scans
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34874
_diffrn_reflns_theta_full        32.23
_diffrn_reflns_theta_max         32.23
_diffrn_reflns_theta_min         2.19
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.059
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         5506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.017
_refine_ls_R_factor_gt           0.0161
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0199P)^2^+0.8178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0427
_refine_ls_wR_factor_ref         0.0431
_reflns_number_gt                5249
_reflns_number_total             5506
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol901565p_si_002.cif
_cod_data_source_block           09jo0016_0m
_cod_database_code               1504119