Synthesis of Multisubstituted Enamides via Pd-Catalyzed Chloroallylation of Ynamides
Zenghui Lu; Wei Kong; Zheliang Yuan; Xueyan Zhao; Gangguo Zhu; Journal of Organic Chemistry 76 (2011) 8524–8529; doi:10.1021/jo2015278

data_4026659
_publ_section_title
;
 Synthesis of Multisubstituted Enamides via Pd-Catalyzed Chloroallylation
 of Ynamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8524
_journal_page_last               8529
_journal_paper_doi               10.1021/jo2015278
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C19 H19 Cl2 N O2 S'
_chemical_formula_sum            'C19 H19 Cl2 N O2 S'
_chemical_formula_weight         396.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.305(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0335(5)
_cell_length_b                   35.053(2)
_cell_length_c                   8.2257(6)
_cell_measurement_reflns_used    1256
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.32
_cell_volume                     1946.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEXII (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II area-detector diffractometer'
_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  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14402
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3411
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0550P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                1853
_reflns_number_total             3411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2015278_si_002.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026659