Copper-Catalyzed Annulative Coupling of <i>S</i>,<i>S</i>-Disubstituted Enones with Diazo Compounds to Access Highly Functionalized Thiophene Derivatives.
He, Yuan; Lou, Jiang; Wu, Ping; Zhou, Yong-Gui; Yu, Zhengkun; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02982

data_4037765
_publ_section_title
;
 Copper-Catalyzed Annulative Coupling of <i>S</i>,<i>S</i>-Disubstituted
 Enones with Diazo Compounds to Access Highly Functionalized Thiophene
 Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02982
_journal_year                    2019
_chemical_formula_sum            'C11 H14 O3 S2'
_chemical_formula_weight         258.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 101.942(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1280(10)
_cell_length_b                   15.5124(19)
_cell_length_c                   8.2549(10)
_cell_measurement_reflns_used    2169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.104
_cell_measurement_theta_min      5.588
_cell_volume                     1268.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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  'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_diffrn_measurement_method       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6535
_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         25.996
_diffrn_reflns_theta_min         3.189
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0042(8)
_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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.3790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1809
_reflns_number_total             2484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02982_si_002.cif
_cod_data_source_block           LJ-C138
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037765
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.956
_shelxl_version_number           2013-4
_shelx_res_checksum              70548
_shelx_hkl_checksum              18061