Direct synthesis of polysubstituted 2-aminothiophenes by Cu(ii)-catalyzed addition/oxidative cyclization of alkynoates with thioamides.
Ge, Li-Shi; Wang, Zheng-Lin; An, Xing-Lan; Luo, Xiaoyan; Deng, Wei-Ping; Organic & biomolecular chemistry 12 (2014) 8473–8479; doi:10.1039/c4ob01534g

data_7154022
_publ_section_title
;
 Direct synthesis of polysubstituted 2-aminothiophenes by Cu(ii)-catalyzed
 addition/oxidative cyclization of alkynoates with thioamides.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8473
_journal_page_last               8479
_journal_paper_doi               10.1039/c4ob01534g
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H17 N O5 S'
_chemical_formula_weight         347.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.351(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7645(9)
_cell_length_b                   7.4690(7)
_cell_length_c                   11.4907(11)
_cell_measurement_reflns_used    4438
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.62
_cell_volume                     834.38(14)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0173
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8491
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_min         2.095
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 2053 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5018
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0556P)^2^+0.0310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4718
_reflns_number_total             5018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob01534g2.cif
_cod_data_source_block           mo_dm14193_0m
_cod_depositor_comments          'Adding full bibliography for 7154022.cif.'
_cod_database_code               7154022
_shelx_estimated_absorpt_t_min   0.907
_shelx_estimated_absorpt_t_max   0.933
_shelxl_version_number           2013-4
_shelx_res_checksum              68640
_shelx_hkl_checksum              19393