One-Pot Two-Component [3 + 2] Cycloaddition/Annulation Protocol for the Synthesis of Highly Functionalized Thiophene Derivatives
Ganesh Chandra Nandi; Subhasis Samai; Maya Shankar Singh; Journal of Organic Chemistry 76 (2011) 8009–8014; doi:10.1021/jo200685e

data_4026594
_publ_section_title
;
 One-Pot Two-Component [3 + 2] Cycloaddition/Annulation Protocol for the
 Synthesis of Highly Functionalized Thiophene Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8009
_journal_page_last               8014
_journal_paper_doi               10.1021/jo200685e
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C15 H12 O5 S'
_chemical_formula_weight         304.31
_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                 89.922(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7109(6)
_cell_length_b                   7.5521(4)
_cell_length_c                   12.9338(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1436.92(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5905
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81223
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                2092
_reflns_number_total             3872
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200685e_si_002.cif
_cod_data_source_block           gr-514
_cod_database_code               4026594