In the title compound, C(13)H(15)FN(2)S, the dihydro-pyrimidine ring is essentially planar, with a maximum deviation of 0.086 (3) Å from the mean plane of the rest of the ring for the dimethyl-ated C atom. The benzene ring is almost perpendicular to the dihydro-pyrimidine ring, with a dihedral angle of 83.97 (14)°. The crystal packing is characterized by centrosymmetric dimers resulting from pairs of inter-molecular N-H⋯S hydrogen bonds. There are also C-H⋯π inter-actions.
IN THE TITLE COMPOUND [SYSTEMATIC NAME: 1-(3-phenyl-prop-2-eno-yl)thio-urea], C(10)H(10)N(2)OS, the acetyl-thio-urea fragment and the phenyl ring adopt an E configuration. The roughly planar but-2-enoyl-thio-urea fragment [maximum deviation = 0.053 (3) Å] forms a dihedral of 10.54 (11)° with the phenyl ring. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked into sheets parallel to (100) by N-H⋯S hydrogen bonds.
In the title compound, C(14)H(16)N(2)O(3)S, the phenyl ring and the ethyl 2-(3-formyl-thio-ureido)acetate fragment adopt an E configuration with respect to the C=C bond. An intra-molecular N-H⋯O hydrogen bond generating an S(6) ring motif is observed. In the crystal, mol-ecules are linked by N-H⋯S, C-H⋯S and C-H⋯O hydrogen bonds, forming sheets lying parallel to the ab plane.
In the title compound, C(13)H(14)N(2)O(3)S, the methyl 2-(3-formyl-thio-ureido)acetate fragment and the phenyl ring adopt an E configuration. The mol-ecule exhibits an intra-molecular N-H⋯O hydrogen bond, which completes a six-membered ring. The crystal packing is stabilized by inter-molecular N-H⋯S contacts, generating a two-dimensional hydrogen-bonding network.
In the title compound, C(11)H(12)N(2)O(3)S, the methyl acetate and benzoyl groups adopt a cis-trans configuration with respect to the thiono S atom across the C-N bonds. An intra-molecular N-H⋯O hydrogen bond is observed. In the crystal packing, mol-ecules are linked by inter-molecular N-H⋯S and C-H⋯O hydrogen bonds to form a two-dimensional network lying parallel to (101).
In the title compound, C(14)H(18)N(2)O(3)S, the butyl acetate fragment and the benzoyl group adopt a cis-trans configuration, respectively, with respect to the thiono S atom across the C-N bonds. In the crystal packing, the mol-ecules are linked by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds to form a one-dimensional chain along the c axis. The terminal butyl C atom is disordered with occupancies 0.82 (2)and 0.18 (2).
The title compound, C(13)H(16)N(2)O(3)S, is a thio-urea derivative with benzoyl and propoxycarbonyl-methyl groups attached to the two terminal N atoms. These groups adopt trans and cis configurations, respectively, with respect to the S atom across the thio-urea C-N bonds. The compound crystallizes in the P2(1)/c space group with Z = 8, resulting in two unique molecules in the asymmetric unit linked by C-H⋯S and C-H⋯O hydrogen bonds, forming a one-dimensional zigzag chain along the c axis.
The title compound, C(12)H(14)N(2)O(3)S, adopts a cis-trans geometry of the thio-urea group and is stabilized by intra-molecular hydrogen bonds between the carbonyl O atoms and the H atom of the thio-amide group and by a C-H⋯S interaction. Mol-ecules are linked by two inter-molecular hydrogen bonds (C-H⋯O and N-H⋯O), forming a one-dimensional chain parallel to the c axis.
In the crystal structure of the title compound, C(8)H(10)N(2)S(2), the molecules are linked by N-H.S hydrogen bonds between the imino group and the thione-S atoms to form a chain along the b axis. The dithiocarbazate moiety is rotated by 85.8 (2) degrees with respect to the phenyl ring.
In the crystal structure of the title compound, C(14)H(12)N(2)O(2), the molecule lies about a twofold axis; two carbonyl groups and the H atoms of the N-N bond are in a trans orientation with respect to each other. In the crystal, each molecule is linked to the other and vice versa by intermolecular N-H.O hydrogen bonds between the amide hydrogen and the O atoms of neighbouring molecules to form two ten-membered rings, each of which has the graph-set motif C4R(2)(2)(10). This extends as a polymeric chain along the c axis.
Two new symmetrical bis-thiourea, 2,2'-[{(terephthaloylbis(azanediyl)bis(carbonothioyl) bis(azanediyl)}dipropanoic acid] (1A) and 3,3'-[{(terephthaloylbis(azanediyl)bis (carbonothioyl)bis(azanediyl)} dipropanoic acid] (1B) were synthesized by the reaction of terephthaloyl chloride with α- and β-alanine in good yields. Their binding properties were investigated with various metal cations using UV-Vis titration experiments. Both isomers exhibited effective binding with Ag(+), Cu(2+), Hg(2+), Pb(2+), Fe(2+) and Fe(3+) cations. However, in the presence of other cations, such as Na(+), Ni(2+), Co(2+), Cd(2+), Zn(2+), Mn(2+), Mg(2+), Ca(2+), Sn(2+), Al(3+), and anions tetrabutylammonium Cl(-) and H2PO4(-), no interaction occurred. Both isomers displayed similar trends towards binding with metal cations.
A new isomers of thiourea derivatives, namely N-(4-chlorobutanoyl)-N'-(2-methylphenyl)-thiourea (1a), N-(4-chlorobutanoyl)-N'-(3-methylphenyl)thiourea (1b) and N-(4-chlorobutanoyl)-N'-(4-methylphenyl)thiourea (1c) have been synthesized by refluxing mixture of equimolar amounts of 4-chlorobutanoylisothiocyanate with 2, 3 or 4-toluidine, respectively. The three isomers were characterized by spectroscopic (UV/vis, FT-IR and NMR) and X-ray crystallography techniques. To investigate the isomerization effect on spectroscopic data, DFT and TD-DFT calculations have been carried out using five hybrid functionals (B3LYP, B3P86, CAM-B3LYP, M06-2X and PBE0) to predict UV/vis absorption bands (n→π∗ and π→π∗), (1)H and (13)C NMR chemical shifts, FT-IR vibration modes and X-ray parameters (bonds, bond angles and torsion angles) for 1a, 1b and 1c isomers. The results showed that the isomerization effect is significant on λ(MAX) absorption bands, while for IR and NMR the effect is negligible. In accordance with previous studies, B3LYP, B3P86 and PBE0 gave the most reliable to predict the excitation energies of thiourea derivatives.
In the title compound, C10H11FN3O3S, the 2-fluoro-benzoyl and proponic acid groups maintain a trans-cis conformation with respect to the thiono C=S bond across their C-N bonds. The propionic acid group adopts an anti conformation about the C-C bond, with an N-C-C-C torsion angle of 173.8 (2)°. The amino groups are involved in the formation of intra-molecular N-H⋯O and N-H⋯F hydrogen bonds. In the crystal, pairs of O-H⋯O hydrogen bonds link mol-ecules into inversion dimers.
The title compound, C10H10BrClN2OS, adopts a trans-cis conformation with respect to the position of the 3-chloro-propanoyl and 4-bromo-phenyl groups, respectively, against the thiono C=S bond across their C-N bonds. The benzene ring makes a dihedral angle of 9.55 (16)° with the N2CS thio-urea moiety. Intra-molecular N-H⋯O and C-H⋯S hydrogen bonds occur. In the crystal, mol-ecules are linked into chains along the c-axis direction by N-H⋯S, C-H⋯S and C-H⋯O hydrogen bonds.
The two independent mol-ecules in the asymmetric unit of the title compound, C11H12Cl2N2OS, exhibit different conformations, with the benzene ring and the N2CS thio-urea group forming dihedral angles of 87.40 (18) and 69.42 (15)°. An intra-molecular N-H⋯O hydrogen bond is present in each mol-ecule. Two further N-H⋯O hydrogen bonds link the independent mol-ecules into a dimer. In the crystal, the dimers are linked by N-H⋯S and C-H⋯S hydrogen bonds, forming chains parallel to the c axis.
The title compound, C13H18N2O2S, adopts a cis conformation between the methyl-benzoyl and thiono groups across their thio-urea C-N bond. However, the methyl-benzoyl group and N2CS thio-urea moiety are twisted by 15.03 (3)°. In the molecule there is an N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by O-H⋯O inter-actions, generating chains extending along the c-axis direction.
In the title compound, C12H15FN2O2S, the mol-ecule adopts a cis configuration of the fluoro-benzoyl group with respect to the thiono group about their C-N bond. The dihedral angle between the fluoro-benzoyl group and the thio-urea N2CS fragment is 69.60 (11)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules form chains along the b-axis direction via O-H⋯S and C-H⋯O hydrogen bonds.
Refluxing a mixture of 1,10-phenanthroline, (4-fluoro-phen-yl)thio-urea and cadmium(II) chloride did not produce the expected mixed-ligand complex but formed a co-crystal of the two ligands, C12H8N2·C7H7FN2S. The asymmetric unit consists of two pairs of the co-crystal mol-ecules. In each (4-fluoro-phen-yl)thio-urea mol-ecule, the planes of the N2CS thio-urea units are almost perpendicular to the corresponding fluoro-benzene rings, subtending angles of 76.53 (7) and 85.25 (7)°. In the crystal, N-H⋯N and N-H⋯S hydrogen bonds form inversion dimers from the co-crystal pairs. A weak π-π inter-action between the phenanthroline rings [centroid-centroid distance = 3.7430 (15)Å] is also observed.
In the title compound, C10H10Cl2N2OS, the mol-ecule adopts a trans-cis conformation with respect to the position of the carbonyl group and the chloro-phenyl groups relative to the thiono group across the C-N bonds. The mol-ecule is stabilized by an N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by N-H⋯S and C-H⋯O hydrogen bonds, forming zigzag chains along the b-axis direction. C-H⋯π inter-actions are also present.
The title compound, C10H9Cl2N3O3S, adopts a trans-cis conformation with respect to the position of chloropropionyl and chloronitrobenzene groups respectively, against the thiono about their C-N bonds. The conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, there is a short Cl⋯Cl contact with a distance of 3.386 (13) Å.