Synthesis of <i>Z</i>-Enamides through Heterogeneous Gold-Catalyzed Stereoselective Hydrogenation of Ynamides.
Lin, Long; Zeng, Xiaojun; Xu, Bo; The Journal of organic chemistry 84 (2019) 11240–11246; doi:10.1021/acs.joc.9b01450

data_4033888
_publ_section_title
;
 Synthesis of <i>Z</i>-Enamides through Heterogeneous Gold-Catalyzed
 Stereoselective Hydrogenation of Ynamides.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11240
_journal_page_last               11246
_journal_paper_doi               10.1021/acs.joc.9b01450
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C16 H17 N O2 S'
_chemical_formula_weight         287.36
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.3270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.45430(10)
_cell_length_b                   7.6941(2)
_cell_length_c                   34.3867(8)
_cell_measurement_reflns_used    9670
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.994
_cell_measurement_theta_min      4.738
_cell_volume                     1443.05(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            16313
_diffrn_reflns_point_group_measured_fraction_full 0.990
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.713
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.044
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.5343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2543
_reflns_number_total             2818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01450_si_002.cif
_cod_data_source_block           mo_dd18154_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4033888
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.974
_shelxl_version_number           2013-4
_shelx_res_checksum              70757
_shelx_hkl_checksum              47124