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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 |

REPOSITORIES: biostudies-literature

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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].

| S-EPMC3344480 | biostudies-literature

5-(3,4,5-Trimeth-oxy-phen-yl)-1,3,4-oxadiazole-2(3H)-thione.

Project description:The two rings in the title compound, C(11)H(12)N(2)O(4)S, are roughly coplanar [dihedral angle = 6.77 (8)°]. Whereas the two outer methyl groups of the three meth-oxy groups are almost coplanar with the aromatic ring to which they are attached [C-C-O-C torsion angles = 8.5 (3) and -8.3 (3)°], the methyl group of the central meth-oxy substituent is not [C-C-C-C = -78.4 (3)°]. The crystal packing is stabilized by N-H⋯O hydrogen bonding.

| S-EPMC3007562 | biostudies-literature

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

Project description:In the title compound, C26H37N5S, the piperazine ring adopts a chair conformation with the exocyclic N-C bonds in pseudo-equatorial orientations. The piperazine ring (all atoms) subtends dihedral angles of 79.47?(9) and 73.07?(9)° with the triazole and benzene rings, respectively, resulting in an approximate U-shape for the mol-ecule. No significant inter-molecular inter-actions are observed in the crystal.

| S-EPMC3885067 | biostudies-literature

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.

| S-EPMC4770969 | biostudies-literature

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.

| S-EPMC2970152 | biostudies-literature

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].

| S-EPMC3393300 | biostudies-literature

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.

| S-EPMC4350721 | biostudies-literature

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

Project description:The title mol-ecule, C(30)H(37)N(5)S, displays a chair-shaped piperazine ring, as well as an approximately planar triazole ring [maximum deviation = 0.002?(2)?Å] whose phenyl substituent is nearly perpendicular to the mean plane of the five-membered ring [dihedral angle = 80.4?(1)°]. The substit-uents on the piperazine ring occupy equatorial sites. Weak inter-molecular C-H?S hydrogen bonding is present in the crystal structure.

| S-EPMC3275028 | biostudies-other

3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-meth-oxy-phen-yl)piperazin-1-yl]meth-yl}-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title compound, C26H37N5OS, the piperazine ring adopts a chair conformation. The triazole ring forms dihedral angles of 67.85?(9) and 59.41?(9)° with the piperazine and benzene rings, respectively, resulting in an approximate V-shaped conformation for the mol-ecule. An intra-molecular C-H?O hydrogen bond generates an S(6) ring motif. The crystal structure features C-H?? inter-actions, producing a two-dimensional supramolecular architecture.

| S-EPMC3914072 | biostudies-literature

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

Project description:The title mol-ecule, C(29)H(35)N(5)S, displays a chair-shaped piperazine ring, as well as an approximately planar triazole ring (r.m.s. deviation = 0.001?Å) whose phenyl substituent is nearly perpendicular to the mean plane of the five-membered ring [dihedral angle = 88.9?(1)°]. The substituents on the piperazine ring occupy equatorial sites. In the crystal, the adamantyl cage is disordered over two sets of sites with a major component of 67.8?(5)%. Weak inter-molecular C-H?S hydrogen bonding is present in the crystal.

| S-EPMC3275029 | biostudies-literature

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