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5-(Adamantan-1-yl)-3-[(4-benzyl-piperazin-1-yl)meth-yl]-1,3,4-oxadiazole-2(3H)-thione.

ABSTRACT: The mol-ecule of the title compound, C(24)H(32)N(4)OS, is a functionalized 1,3,4-oxadiazole-2-thione with substituted piperazine and adamantanyl substituents attached at the 3- and 5-positions, respectively, of the oxadiazole spacer with an approximately C-shaped conformation. In the crystal, mol-ecules form dimers via C-H⋯S inter-action. The piperazine ring has a chair conformation; the substituents S, methyl-ene C and adamantane C of the essentially planar oxadiazole ring are approximately in the same plane, with distances of -0.046 (2), -0.085 (5) and 0.003 (4) Å, respectively. The dihedral angle between the planes of the phenyl and oxadiazole rings is 31.3 (3)°.

SUBMITTER: El-Emam AA

PROVIDER: S-EPMC3393978 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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5-(Adamantan-1-yl)-3-[(4-benzyl-piperazin-1-yl)meth-yl]-1,3,4-oxadiazole-2(3H)-thione.

El-Emam Ali A AA El-Brollosy Nasser R NR Attia Mohamed I MI Said-Abdelbaky Mohammed M García-Granda Santiago S

Acta crystallographica. Section E, Structure reports online 20120623 Pt 7

The mol-ecule of the title compound, C(24)H(32)N(4)OS, is a functionalized 1,3,4-oxadiazole-2-thione with substituted piperazine and adamantanyl substituents attached at the 3- and 5-positions, respectively, of the oxadiazole spacer with an approximately C-shaped conformation. In the crystal, mol-ecules form dimers via C-H⋯S inter-action. The piperazine ring has a chair conformation; the substituents S, methyl-ene C and adamantane C of the essentially planar oxadiazole ring are approximately in ...[more]

PMID: 22798843

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3-[(N-Methyl-anilino)meth-yl]-5-(thio-phen-2-yl)-1,3,4-oxadiazole-2(3H)-thione.

Project description:In the title compound, C(14)H(13)N(3)OS(2), the thio-phene ring is disordered over two orientations by ca 180° about the C-C bond axis linking the ring to the rest of the mol-ecule, with a site-occupancy ratio of 0.651 (5):0.349 (5). The central 1,3,4-oxadiazole-2(3H)-thione ring forms dihedral angles of 9.2 (5), 4.6 (11) and 47.70 (7)° with the major and minor parts of the disordered thio-phene ring and the terminal phenyl ring, respectively. In the crystal, no significant inter-molecular hydrogen bonds are observed. The crystal packing is stabilized by π-π inter-actions [centroid-centroid distance = 3.589 (2) Å].

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Crystal structure of 3-{[4-(2-meth-oxy-phen-yl)piperazin-1-yl]meth-yl}-5-(thio-phen-2-yl)-1,3,4-oxa-diazole-2(3H)-thione.

Project description:The title compound, C18H20N4O2S2, is a new 1,3,4-oxa-diazole and a key pharmacophore of several biologically active agents. It is composed of a meth-yl(thio-phen-2-yl)-1,3,4-oxa-diazole-2(3H)-thione moiety linked to a 2-meth-oxy-phenyl unit via a piperazine ring that has a chair conformation. The thio-phene ring mean plane lies almost in the plane of the oxa-diazole ring, with a dihedral angle of 4.35 (9)°. The 2-meth-oxy-phenyl ring is almost normal to the oxa-diazole ring, with a dihedral angle of 84.17 (10)°. In the crystal, mol-ecules are linked by weak C-H⋯S hydrogen bonds and C-H⋯π inter-actions, forming layers parallel to the bc plane. The layers are linked via weak C-H⋯O hydrogen bonds and slipped parallel π-π inter-actions [inter-centroid distance = 3.6729 (10) Å], forming a three-dimensional structure. The thio-phene ring has an approximate 180° rotational disorder about the bridging C-C bond.

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3-(Adamantan-1-yl)-1-[(4-benzyl-piperazin-1-yl)meth-yl]-4-[(E)-(2-hy-droxy-benzyl-idene)amino]-1H-1,2,4-triazole-5(4H)-thione.

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5-[1-(3,4-Dichloro-phen-oxy)eth-yl]-1,3,4-oxadiazole-2(3H)-thione hemihydrate.

Project description:In the title compound, C(10)H(8)Cl(2)N(2)O(2)S·0.5H(2)O, the atoms in the oxadiazole ring are essentially coplanar (r.m.s. deviation 0.010 Å). The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds involving the water mol-ecule, which is situated on an a twofold rotation axis, and two organic mol-ecules, leading to a thione tautomer in the solid state. The C atom attached to the oxadiazole ring adopts a typical sp(3) hybridization. The dihedral angle between the mean plane of the benzene ring of the dichloro-phenyl group and the mean plane of the oxadiazole ring is 74.18 (4)°. The crystal structure is stabilized by intermolecular N-H⋯O and O-H⋯S hydrogen bonds.

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3-(Adamantan-1-yl)-4-[(E)-(2,6-difluoro-benzyl-idene)amino]-1-[(4-phenyl-piperazin-1-yl)meth-yl]-1H-1,2,4-triazole-5(4H)-thione.

Project description:The imine residue [C=N = 1.268?(3)?Å; conformation = E] is twisted [N-N-C-N = 87.8?(2)°] out of the plane (r.m.s. deviation = 0.016?Å) of the central 1,2,4-triazole ring in the title compound, C(30)H(34)F(2)N(6)S. A small twist also occurs between the imine and terminal benzene rings [N-C-C-C = -169.8?(2)°]. The piperazine ring (chair conformation) occupies a position almost normal to the central plane [N-N-C-N = 87.8?(2)°]. In the crystal, the mol-ecules are consolidated into a three-dimensional architecture via C-H?S, C-H?? and ?-? inter-actions, the latter between centrosymmetrically related difluoro-benzene rings [inter-centroid distance = 3.9389?(18)?Å].

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Crystal structure of 3-[(4-benzyl-piperazin-1-yl)meth-yl]-5-(thio-phen-2-yl)-2,3-di-hydro-1,3,4-oxa-diazole-2-thione.

Project description:The title 1,3,4-oxa-diazole-2-thione derivative, C18H20N4OS2, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The 2-thienyl rings in both mol-ecules are rotationally disordered over two orientations by approximately 180° about the single C-C bond that connects it to the oxa-diazole thione ring; the ratios of site occupancies for the major and minor components were fixed in the structure refinement at 0.8:0.2 and 0.9:0.1 in mol-ecules A and B, respectively. The 1,3,4-oxa-diazole-2-thione ring forms dihedral angles of 7.71 (16), 10.0 (11) and 77.50 (12)° (mol-ecule A), and 6.5 (3), 6.0 (9) and 55.30 (12)° (mol-ecule B) with the major and minor parts of the disordered thio-phene ring and the mean plane of the adjacent piperazine ring, respectively, resulting in approximately V-shaped conformations for the mol-ecules. The piperazine ring in both mol-ecules adopts a chair conformation. The terminal benzene ring is inclined towards the mean plane of the piperazine ring with N-C-C-C torsion angles of -58.2 (3) and -66.2 (3)° in mol-ecules A and B, respectively. In the crystal, no inter-molecular hydrogen bonds are observed. The crystal packing features short S⋯S contacts [3.4792 (9) Å] and π-π inter-actions [3.661 (3), 3.664 (11) and 3.5727 (10) Å], producing a three-dimensional network.

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3-(Adamantan-1-yl)-1-[(4-ethyl-piperazin-1-yl)meth-yl]-4-[(E)-(4-hy-droxy-benzyl-idene)amino]-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title thione, C(26)H(36)N(6)OS, the 1,2,4-triazole ring is planar (r.m.s. deviation = 0.020?Å) and the benzene ring is twisted out of this plane [dihedral angle = 62.35?(12)°]. Supra-molecular zigzag chains feature in the crystal packing. These are sustained by O-H?N(piperazine) hydrogen bonds, and are connected into the three-dimensional crystal structure by C-H?S and C-H?O inter-actions. The crystal studied was a racemic twin.

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