Related Articles

The mol­ecule of the title thia­diazole derivative, C11H11N3O2S2, has a butterfly-like structure and the whole mol­ecule is disordered with a site-occupancy ratio of 0.629 (4):0.371 (4). The mol­ecule is disordered in such a way that the 3-methyl-4-nitro­phenyl units of the major and minor components are approximately related by 180° rotation around the C—N bond axis. The dihedral angle between the 1,3,4-thia­diazole and benzene rings is 70.8 (4)° in the major component and 74.9 (6)° in the minor component. In the crystal, mol­ecules are arranged into screw chains along the c axis. These chains are stacked along the b axis. Weak inter­molecular C—H⋯O and C—H⋯π inter­actions and a short C⋯O contact [3.005 (7) Å] are present.

In the title compound, C12H12N6S4, the two terminal thia­diazole rings are twisted with respect to the central benzene ring, making dihedral angles of 54.28 (4) and 76.56 (3)°. The dihedral angle between the two thia­diazole rings is 27.77 (4)°. Inter­molecular N—H⋯N hydrogen bonds stabilize the crystal packing, linking the mol­ecules into a tape along the b axis.

The title mol­ecule, C11H12N2OS2, is twisted with a dihedral angle of 83.63 (12)° between the 1,3,4-thia­diazole and benzene rings. The meth­oxy group deviates slightly from the attached benzene ring, with a C—C—O—C torsion angle of 4.2 (4)°. In the crystal, mol­ecules are linked by weak C—H⋯N inter­actions and stacked along the c axis.

In the title compound, C16H22N2OS2, the S atom of the thia­diazole ring and the attached methyl groups are disordered over two orientations with a refined site-occupancy ratio of 0.641 (11):0.359 (11). The thia­diazole ring is in a twist conformation in both disorder components. The mean plane through the thia­diazole ring makes dihedral angles of 77.39 (8) (major component) and 67.45 (11)° (minor component) with the benzene ring. Intra­molecular C—H⋯N inter­actions generate two S(6) ring motifs. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into zigzag chains parallel to the b axis.

The complete mol­ecule of the title compound, C16H12Cl2N2S3, is generated by crystallographic twofold symmetry, with the S atom of the thiadiazole ring lying on the rotation axis. The dihedral angle between the mean planes of the 1,3,4-thia­diazole and benzene rings is 87.19 (7)°. In the crystal, mol­ecules are linked by C—H⋯N inter­actions and short S⋯S contacts [3.3389 (9) Å] occur.

In the title compound, C18H13Cl2N3OS, the eight atoms comprising the central imidazo/thia­diazo­lethia­diazole residue are coplanar (r.m.s. deviation = 0.009 Å). The dihedral angle of 8.72 (13)° between the dichloro­benzene and tolyl rings reflects a twist about the O—C(benzene) bond; the Cm—O—Cb—Cb torsion angle = −168.5 (2)° (m = methyl­ene C and b is benzene C). Supra­molecular tapes along the b axis are found in the crystal structure which are mediated by π–π inter­actions occurring between centrosymmetrically related thia­diazole rings [inter-ring centroid distance = 3.6907 (16) Å] and between the benzene and tolyl rings [inter-ring centroid distance = 3.7597 (16) Å].

In the mol­ecule of the title compound, C19H18N4O3S, the planar central heterocylic ring system is oriented with respect to the trimethoxy­phenyl and 2-methyl­phenyl rings at dihedral angles of 4.43 (3) and 4.32 (3)°, respectively. The dihedral angle between the two benzene rings is 7.65 (4)°. In the crystal structure, inter­molecular C—H⋯N hydrogen bonds link the mol­ecules into centrosymmetric R 2 2(18) dimers. These dimers are connected via a C—H⋯π contact between the 2-methyl­phenyl and trimethoxy­phenyl rings, and a π–π contact between the thia­diazole and trimethoxy­phenyl rings [interplanar distance 3.51 Å, dihedral angles 4.17(4)°]. An intramolecular C—H⋯N hydrogen bond is also present.

The title compound, C20H23N4O6PS, was synthesized by the reaction of N-(4-methoxy­benzyl­idene)-5-(4-nitro­phen­yl)-1,3,4-thia­diazol-2-amine and diethyl phosphite. The thia­diazole and nitro-substituted phenyl rings in the mol­ecule are approximately coplanar, the dihedral angle being 5.3 (2)°. The dihedral angle formed by the mean plane through all non-H atoms of both the thia­diazole and the nitro-substituted phenyl ring with the plane of the meth­oxy-substituted phenyl ring is 48.9 (2)°. In the crystal structure, mol­ecules form centrosymmetric dimers as a result of N—H⋯O bonds involving amine H and phosphine oxide O atoms.

The thia­diazoyl and sulfonyl-benzene rings in the title compound, C20H23N3O3S3, are aligned to the same side of the mol­ecule, forming a twisted ‘U’ shape [dihedral angle = 77.6 (5)°]. The benzyl-benzene ring is orientated in the opposite direction from the mol­ecule but projects approximately along the same axis as the other rings [dihedral angle between benzene rings = 28.2 (5)°] so that, overall, the mol­ecule has a flattened shape. The hy­droxy and amine groups are almost syn which enables the formation of inter­molecular hy­droxy-OH⋯N(thia­diazo­yl) and amine-H⋯O(sulfon­yl) hydrogen bonds leading to a supra­molecular chain aligned along the a axis.

In the title mol­ecule, C16H16BrN5O3S, the 1,3,4-thia­diazole ring is situated under the benzene ring, forming a dihedral angle of 86.6 (2)°, and with an S⋯Cg (where Cg is the centroid of the benzene ring) distance of 3.312 (3) Å. The benzene and 1,3,4-thia­diazole rings form dihedral angles of 83.8 (3) and 57.7 (2)°, respectively, with the central pyrazole ring. In the absence of classical hydrogen bonds, the crystal packing is stabilized by a C—H⋯π inter­action..

The asymmetric unit of the title compound, C9H9N3S, contains two crystallographically independent mol­ecules, in which the thia­diazole and tolyl rings are oriented at dihedral angles of 32.25 (3) and 74.50 (3)°. An intra­molecular C—H⋯S inter­action results in the formation of a five-membered ring. In the crystal structure, inter­molecular N—H⋯N hydrogen bonds link the mol­ecules into chains along the a axis. A π–π contact between the thia­diazole rings [centroid–centroid distance = 3.910 (3) Å] may further stabilize the structure. There is also a weak C—H⋯π inter­action.

The title compound, C18H14FN3O2S2, was synthesized by the reaction of 5-(4-fluoro­phen­yl)-N-(4-methoxy­benzyl­idene)-1,3,4-thia­diazol-2-amine and mercaptoacetic acid. The thia­zolidinone ring adopts a twist conformation. The 4-methoxy­phenyl ring is almost perpendicular to the thia­diazole ring, making a dihedral angle of 88.4 (3)°. The 4-fluoro­phenyl ring is nearly coplanar with the thia­diazole ring, the dihedral angle being 6.8 (3)°. The crystal structure involves C—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds.

The title compound, C19H15Cl2N3OS2, was synthesized by the reaction of N-(2,4-dichloro­phen­yl)-5-(3,5-dimethyl­phen­yl)-1,3,4-thia­diazol-2-amine and mercaptoacetic acid. The thia­zolidinone ring adopts a twist conformation. The 2,4-dichloro­phenyl ring is almost perpendicular to the thia­diazole ring, the dihedral angle being 82.8 (2)°. The 3,5-dimethyl­phenyl ring is nearly coplanar with the thia­diazole ring, the dihedral angle being 2.7 (2)°. An intramolecular C—H⋯N hydrogen bond is present.

In the mol­ecule of the title compound, C17H15N3O3S·0.5H2O, the thia­diazole ring is oriented with respect to the two 2-methoxy­phenyl rings at dihedral angles of 3.70 (3) and 1.74 (2)°. An intra­molecular N—H⋯O hydrogen bond results in the formation of a planar six-membered ring, which is oriented with respect to the thia­diazole ring at a dihedral angle of 1.33 (3)°. Thus, all of the rings are nearly coplanar. In the crystal structure, inter­molecular O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules.

The title compound, C9H9N3S, was synthesized by the reaction of 4-methyl-benzoic acid and thio­semicarbazide. The thia­diazol ring adopts a planar conformation and makes a dihedral angle of 31.19 (18)° with the phenyl ring. In the crystal, mol­ecules are linked by N—H⋯N hydrogen bonds.

There are two independent mol­ecules in the asymmetric unit of the title compound, C19H24S2. In both mol­ecules, the aliphatic segment of the ligand is in an all-trans conformation: the –S–(CH2)5–S–bridging chain is almost planar (r.m.s. deviation for all non-H atoms = 0.0393 and 0.0796 Å in the two mol­ecules) and maximally extended. Their mean planes form dihedral angles of 4.08 (6)/20.47 (6) and 2.22 (6)/58.19 (6)° with the aromatic rings in the two mol­ecules. The crystal packing is purely governed by weak inter­molecular forces.

In the title compound, C17H11FN4O3S2, the five-membered thia­zolidinone and thia­diazole rings are almost planar, with r.m.s. deviations of 0.017 and 0.0019 Å, respectively. The 4-fluoro­phenyl ring is almost perpendicular to the thia­diazole ring, making a dihedral angle of 89.5 (3)°. The 4-nitro­phenyl ring is nearly coplanar with the thia­diazole ring, the dihedral angle being 7.9 (3)°. The crystal structure is stabilized by two inter­molecular C—H⋯O hydrogen bonds.

The asymmetric unit of the title compound, C17H12N4S4, contains one half-mol­ecule situated on a twofold rotational axis. In the mol­ecule, the thia­diazole and attached phenyl rings are twisted by 5.8 (3)°.

The bidentate 1,3,4-thia­diazole ligand substituted by two 2-pyridyl rings (denoted L) has been found to produce the new monomeric title complex, [Co(C12H8N4S)2(H2O)2](BF4)2. The thia­diazole and pyridyl rings surrounding the Co atom are almost coplanar [dihedral angle = 4.35 (7)°]. The mean plane defined by these heterocyclic moieties makes a dihedral angle of 18.72 (6)° with the non-coordinated pyridyl ring. The Co2+ cation, located at a crystallographic center of symmetry, is bonded to two ligands and two water mol­ecules in a trans configuration in an octa­hedral environment. The tetra­fluorido­­borate ions can be regarded as free anions in the crystal lattice. Nevertheless, they are involved in an infinite two-dimensional network along the [010] and [101] directions of O—H⋯F hydrogen bonds.

The title compound, C18H17N3S2, was synthesized by the reaction of 5-(3,5-dimethyl­phen­yl)-1,3,4-thia­diazol-2-amine and 4-(methyl­sulfan­yl)benzaldehyde. An intra­molecular C—H⋯S hydrogen bond results in the formation of a planar (r.m.s. deviation = 0.003 Å) five-membered ring. In the crystal structure, inter­molecular C—H⋯N hydrogen bonds link the mol­ecules to form layers parallel to (011).

In the title compound, C10H8ClN3S, the dihedral angle between the mean planes of the benzene and imidazo[2,1-b][1,3,4]thia­diazole rings is 6.0 (9)°. In the crystal, mol­ecules are assembled by the formation of centrosymmetric dimers by π-stacking of the thia­diazole and benzene rings of neighboring mol­ecules [centroid–centroid distance = 3.6938 (11) Å] along [010].

In the title compound, C17H13ClN4OS, the 1,3,4-thia­diazole ring makes dihedral angles of 9.70 (15) and 7.22 (10)° with the benzene and phenyl rings, respectively; the dihedral angle between these two rings is 6.37 (19)°. In the crystal, pairs of N—H⋯N and C—H⋯O hydrogen bonds between inversion-related mol­ecules result in supra­molecular ribbons displaying alternate R 2 2(8) and R 2 2(14) graph-set ring motifs.

In the mol­ecule of the title compound, C11H15N5OS2, the thia­diazole and triazole rings are not coplanar, the dihedral angle formed by their mean planes being 59.9 (2)°. The exocyclic S atom, and the methyl­ene, carbonyl, tert-butyl and one methyl carbon form an approximately planar zigzag chain, which makes a dihedral angle of 74.6 (1)° with the thia­diazole ring.

In the mol­ecule of the title compound, C18H13Cl2N3O2S2, the thia­zolidinone ring has an envelope conformation with the S atom displaced by 0.394 (3) Å from the plane of the other ring atoms. The thia­diazole ring is oriented at a dihedral angle of 7.40 (4)° with respect to the 4-methoxy­phenyl ring. Intra­molecular C—H⋯S, C—H⋯N and C—H⋯Cl hydrogen bonds result in the formation of two planar and two non-planar five-membered rings. The planar five-membered rings are oriented at a dihedral angle of 6.23 (3)°. The 2,4-dichloro­phenyl ring is oriented at dihedral angles of 84.21 (4) and 83.55 (3)° with respect to the thia­diazole and 4-methoxy­phenyl rings, respectively. In the crystal structure, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers.

The asymmetric unit of the title compound, C21H20N4O3S, contains two independent mol­ecules. The dihedral angles between the two benzene rings are 47.6 (1) and 30.2 (1)°, the corresponding values between the p-methoxy­benzene and thia­diazol rings are 12.3 (1) and 24.7 (1)°, respectively, for the two mol­ecules. The conformations of the N—H and C=O bonds are anti with respect to each other. The enone groups show a trans configuration. The crystal structure is stabilized by N—H⋯O and N—H⋯N inter­actions. The absolute structure could not be determined from the X-ray data but the absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.