Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters
Ganesh Chandra Nandi; Subhasis Samai; Maya Shankar Singh; Journal of Organic Chemistry 75 (2010) 7785–7795; doi:10.1021/jo101572c

data_4025822
_publ_section_title
;
 Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized
 Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via
 Ring Annulation with \b-Oxodithioesters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7785
_journal_page_last               7795
_journal_paper_doi               10.1021/jo101572c
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C23 H20 N4 O4 S2'
_chemical_formula_weight         480.55
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 115.11(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.020(7)
_cell_length_b                   10.502(2)
_cell_length_c                   14.458(2)
_cell_measurement_temperature    293(2)
_cell_volume                     4539.9(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.833
_diffrn_measured_fraction_theta_max 0.676
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6639
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83792
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0916P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                2318
_reflns_number_total             4179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101572c_si_003.cif
_cod_data_source_block           gr-328
_cod_original_cell_volume        4540.1(15)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4025822