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

ABSTRACT: 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.

SUBMITTER: Al-Abdullah ES

PROVIDER: S-EPMC3885067 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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

Al-Abdullah Ebtehal S ES Al-Tuwaijri Hanaa M HM El-Emam Ali A AA Chidan Kumar C S CS Fun Hoong-Kun HK

Acta crystallographica. Section E, Structure reports online 20131123 Pt 12

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. ...[more]

PMID: 24454243

Similar Datasets

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

Project description:The title compound, C(25)H(35)N(5)S, has an approximately C-shaped conformation. The dihedral angle between the triazole and phenyl planes is 79.5?(2)°. The crystal structure consists of infinite chains parallel to the b axis, constructed by C-H?S hydrogen bonds between translation-related mol-ecules. Adjacent chains are linked via weak C-H?C inter-actions between the adamantyl and phenyl groups.

| S-EPMC3414308 | biostudies-literature

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-benzyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:The title compound, C19H23N3S, is a functionalized triazoline-3-thione derivative. The benzyl ring is almost normal to the planar 1,2,4-triazole ring (r.m.s. deviation = 0.007?Å) with a dihedral angle of 86.90?(7)°. In the crystal, molecules are linked by pairs of N-H?S hydrogen bonds, forming inversion dimers that enclose R 2 (2)(8) loops. The crystal packing is further stabilized by weak C-H?? inter-actions that link adjacent dimeric units into supra-molecular chains extending along the a-axis direction.

| S-EPMC4120616 | biostudies-literature

3-(Adamantan-1-yl)-4-ethyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title compound, C(14)H(21)N(3)S, the 1,2,4-triazole ring is nearly planar, with a maximum deviation of 0.003 (4) Å. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯S hydrogen bonds.

| S-EPMC3344481 | 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

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

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-methyl-1-[(4-phenyl-piperazin-1-yl)meth-yl]-1H-1,2,4-triazole-5(4H)-thione dichloro-methane hemisolvate.

Project description:The asymmetric unit of the title dichloro-methane hemisolvate, C(24)H(33)N(5)S·0.5CH(2)Cl(2), comprises an adamantan-yl/triazole derivative and half a CH(2)Cl(2) mol-ecule of crystallization; the latter is disordered about a twofold axis of symmetry. The piperazine ring has a chair conformation and the two N-bound substituents occupy equatorial positions. The piperazine residue is almost normal to the triazole ring [N-N-C-N torsion angle = -79.9?(3)°] so that to a first approximation, the mol-ecule has an L-shape. Linear supra-molecular chains parallel to [001] are formed via C-H?S inter-actions. Two such chains are linked into a double chain via C-H?Cl inter-actions involving the disordered CH(2)Cl(2) mol-ecules of solvation.

| S-EPMC3379353 | biostudies-literature

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.

| S-EPMC3295449 | biostudies-other

3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione.

Project description:The title compound, C(11)H(13)N(3)S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77?(2):0.23?(2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002?(3)?Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94?(18) and 86.56?(49)° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55?(15)° and this conformation is stabilized by an intra-molecular C-H?S contact. In the crystal, pairs of N-H?S hydrogen bonds link mol-ecules into inversion dimers. ?-? inter-actions are observed between the triazole and benzene rings, with centroid-centroid separations of 3.547?(4) and 3.544?(12)?Å for components A and B, and slippages of 0.49?(6) and 0.58?(15)?Å, respectively.

| S-EPMC3569223 | biostudies-literature

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