3-Mercaptopropionic acid-nitrile imine adducts. An unprecedented cyclization into 1,3,4-thiadiazol-2(3H)-ones and -2(3H)-thiones.
Zahra, Jalal A.; Abu Thaher, Bassam A.; El-Abadelah, Mustafa M; Boese, Roland; Organic & biomolecular chemistry 3 (2005) 2599–2603; doi:10.1039/b505010c

data_7150178
_publ_section_title
;
 3-Mercaptopropionic acid-nitrile imine adducts. An unprecedented
 cyclization into 1,3,4-thiadiazol-2(3H)-ones and -2(3H)-thiones.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2599
_journal_page_last               2603
_journal_paper_doi               10.1039/b505010c
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C22 H20 N4 O4 S2'
_chemical_formula_weight         468.54
_chemical_name_common
5-Acetyl-3-(4-methylphenyl)-1,3,4-thiadiazol-2(3H)-one
_space_group_IT_number           14
_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                 107.916(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9376(16)
_cell_length_b                   14.0036(19)
_cell_length_c                   13.9101(19)
_cell_measurement_temperature    203(2)
_cell_volume                     2212.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27847
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.278
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.8776P] where
P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                4467
_reflns_number_total             5545
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b505010c.txt
_cod_data_source_block           ubkabam
_cod_database_code               7150178