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_4025821
_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            'C18 H19 N3 O5 S3'
_chemical_formula_weight         453.57
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.017(8)
_cell_angle_beta                 79.403(7)
_cell_angle_gamma                83.563(7)
_cell_formula_units_Z            2
_cell_length_a                   8.6327(7)
_cell_length_b                   9.9878(9)
_cell_length_c                   13.1649(12)
_cell_measurement_reflns_used    2797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0384
_cell_measurement_theta_min      3.0039
_cell_volume                     1040.43(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.843
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8148
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         3.01
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.803
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1008P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1721
_reflns_number_gt                2565
_reflns_number_total             4704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101572c_si_002.cif
_cod_data_source_block           gn
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1040.43(16)
_cod_database_code               4025821