Amide Bond Formation Assisted by Vicinal Alkylthio Migration in Enaminones: Metal- and CO-Free Synthesis of α,β-Unsaturated Amides.
Liu, Zhuqing; Huang, Fei; Wu, Ping; Wang, Quannan; Yu, Zhengkun; The Journal of organic chemistry 83 (2018) 5731–5750; doi:10.1021/acs.joc.8b00775

data_4034794
_publ_section_title
;
 Amide Bond Formation Assisted by Vicinal Alkylthio Migration in
 Enaminones: Metal- and CO-Free Synthesis of \a,\b-Unsaturated Amides.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5731
_journal_page_last               5750
_journal_paper_doi               10.1021/acs.joc.8b00775
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C16 H18 F N O3 S'
_chemical_formula_weight         323.37
_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   mixed
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_cell_angle_alpha                90
_cell_angle_beta                 91.648(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2705(3)
_cell_length_b                   14.2552(11)
_cell_length_c                   21.5780(15)
_cell_measurement_reflns_used    1807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.132
_cell_measurement_theta_min      4.108
_cell_volume                     1620.53(19)
_computing_cell_refinement       'Bruker SMART'
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_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         3.010
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.182
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_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+0.4247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2305
_reflns_number_total             3189
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00775_si_002.cif
_cod_data_source_block           lzq-136a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034794
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.972
_shelxl_version_number           2013-4
_shelx_res_checksum              80059
_shelx_hkl_checksum              46154