Copper-mediated intramolecular oxidative C-H/N-H cross-coupling of alpha-alkenoyl ketene N,S-acetals to synthesize pyrrolone derivatives
Fei Huang; Ping Wu; Liandi Wang; Jiping Chen; Chenglin Sun; Zhengkun Yu; Chem.Commun. 50 (2014) 12479–; doi:10.1039/C4cc05837B

data_7115763
_publ_section_title
;
 Copper-mediated intramolecular oxidative C-H/N-H cross-coupling of
 alpha-alkenoyl ketene N,S-acetals to synthesize pyrrolone derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              12479
_journal_paper_doi               10.1039/C4cc05837B
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C16 H12 Cl N O S2'
_chemical_formula_weight         333.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                110.442(3)
_cell_angle_beta                 98.772(4)
_cell_angle_gamma                103.159(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4568(11)
_cell_length_b                   10.4808(16)
_cell_length_c                   10.804(3)
_cell_measurement_reflns_used    3741
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.18
_cell_volume                     745.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      140(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.984
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
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_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.554
_diffrn_reflns_theta_min         2.080
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
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_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0773P)^2^+0.3292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3825
_reflns_number_total             4501
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           dm13437
_cod_original_cell_volume        745.1(2)
_cod_database_code               7115763
_shelx_estimated_absorpt_t_min   0.924
_shelx_estimated_absorpt_t_max   0.959
_shelxl_version_number           2013-4
_shelx_res_checksum              86509