Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure.
Kumar, Sonu; Cruz-Hernández, Carlos; Pal, Shilpi; Saunthwal, Rakesh K.; Patel, Monika; Tiwari, Rakesh K.; Juaristi, Eusebio; Verma, Akhilesh K.; The Journal of organic chemistry  (2015) –; doi:10.1021/acs.joc.5b01647

data_4031722
_publ_section_title
;
 Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl
 Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.5b01647
_journal_year                    2015
_chemical_formula_moiety         'C18 H13 N S'
_chemical_formula_sum            'C18 H13 N S'
_chemical_formula_weight         275.35
_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                 108.70(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.661(3)
_cell_length_b                   8.1860(12)
_cell_length_c                   12.112(2)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.95
_cell_volume                     1376.9(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur Sapphire3'
_diffrn_measurement_method       '\w 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  0.0784
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9741
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9589
_exptl_absorpt_correction_T_min  0.9485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0831P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1757
_reflns_number_gt                1583
_reflns_number_total             2426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01647_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1376.8(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4031722