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6-(1-Adamant-yl)-3-(2-fluoro-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

ABSTRACT: In the title compound, C(19)H(19)FN(4)S, the planes of the 2-fluoro-phenyl and 1,2,4-triazolo[3,4-b][1,3,4]thia-diazole ring systems are oriented at a dihedral angle of 48.98?(6)°. In the crystal, weak C-H?S and C-H?? inter-actions may help to establish the packing and ?-? inter-actions between the centroids of the benzene rings at a distance of 3.8792?(13)?Å occur.

SUBMITTER: Khan MU

PROVIDER: S-EPMC2969597 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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6-(1-Adamant-yl)-3-(2-fluoro-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Khan Mahmood-Ul-Hassan MU Hameed Shahid S Tahir M Nawaz MN Bokhari Tanveer Hussain TH Khan Islam Ullah IU

Acta crystallographica. Section E, Structure reports online 20090529 Pt 6

In the title compound, C(19)H(19)FN(4)S, the planes of the 2-fluoro-phenyl and 1,2,4-triazolo[3,4-b][1,3,4]thia-diazole ring systems are oriented at a dihedral angle of 48.98 (6)°. In the crystal, weak C-H⋯S and C-H⋯π inter-actions may help to establish the packing and π-π inter-actions between the centroids of the benzene rings at a distance of 3.8792 (13) Å occur. ...[more]

PMID: 21583277

Similar Datasets

6-(1-Adamant-yl)-3-(2-chloro-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the title compound, C(19)H(19)ClN(4)S, the 2-chloro-phenyl and [1,2,4]triazolo[3,4-b] [1,3,4]thia-diazole fragments (r.m.s. deviations of 0.015 and 0.017 Å, respectively) are oriented at a dihedral angle of 55.76 (6)°. The adamantane group exhibits extensive rotational disorder about the single C-C bond to the thia-diazole ring, which was modelled as occupying four orientations each with 0.25 occupancy. In the crystal, the chloro-phenyl rings exhibit π-π stacking inter-actions with centroid-centroid distances of 3.9526 (18) Å.

| S-EPMC3099922 | biostudies-literature

6-(Adamantan-1-yl)-3-(3-fluoro-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:The title mol-ecule, C(19)H(19)FN(4)S, displays C(s) mol-ecular symmetry, in which the crystallographic mirror plane bis-ects the adamantan-1-yl unit while the 3-fluoro-phenyl triazole ring is located on the mirror plane. The F atom of the 3-fluoro-phenyl ring is positionally disordered [occupancy ratio 0.9:0.1]. In the crystal, ?-? inter-actions between the triazole and phenyl rings occur [centroid-centroid distance = 3.5849?(7)?Å] and weak C-H?F inter-actions form a ribbon propagating in [010].

| S-EPMC3011398 | biostudies-literature

3-(2-Fluoro-phen-yl)-6-(phenoxy-meth-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:The crystal structure of the title compound, C(16)H(11)FN(4)OS, was synthesized in the course of our studies on 1,2,4-triazolo[3,4-b][1,3,4]thia-diazo-les as inhibitors of p38 mitogen-activated protein kinase (MAPK). The three-dimensional data obtained were used to generate a three-dimensional pharmacophore model for in silico database screening. The dihedral angles between the central heterocylic system and the fluoro-phenyl and phenyl rings are 20.21?(3) and 5.43?(1)°, respectively; the dihedral angle between the two benzene rings is 15.80?(4)°.

| S-EPMC2961052 | biostudies-literature

3,6-Bis(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the mol-ecule of the title compound, C(21)H(22)N(4)O(6)S, the planar central heterocyclic ring system is oriented with respect to the trimethoxy-phenyl rings at dihedral angles of 2.60?(5) and 3.60?(6)°. Intra-molecular C-H?N and C-H?S hydrogen bonds result in the formation of planar five- and six-membered rings. In the crystal structure, inter-molecular C-H?O hydrogen bonds link the mol-ecules. There is a C-H?? contact between a methyl group and a trimethoxy-phenyl ring, and a ?-? contact between the central heterocyclic ring system and a trimethoxy-phenyl ring [centroid-centroid distance = 3.640?(1)?Å].

| S-EPMC2962044 | biostudies-literature

3-Ethyl-6-[3-(4-fluoro-phen-yl)-1H-pyrazol-4-yl]-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the title compound, C(14)H(11)FN(6)S, the 1,2,4-triazolo[3,4-b][1,3,4]thia-diazole ring system is essentially planar [maximum deviation = 0.022?(3)?Å] and is inclined at dihedral angles of 15.00?(18) and 52.82?(16)° with respect to the pyrazole and phenyl rings. In the crystal, mol-ecules are linked into two-dimensional networks parallel to (100) via inter-molecular N-H?N and weak C-H?N hydrogen bonds. The crystal packing is further consolidated by weak ?-? stacking inter-actions, with a centroid-centroid distance of 3.590?(2)?Å. The crystal studied was an inversion twin with a 0.37?(13):0.63?(13) domain ratio.

| S-EPMC3009212 | biostudies-literature

6-(2-Methyl-phen-yl)-3-(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the mol-ecule of the title compound, C(19)H(18)N(4)O(3)S, the planar central heterocylic ring system is oriented with respect to the trimethoxy-phenyl and 2-methyl-phenyl 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, inter-molecular C-H?N hydrogen bonds link the mol-ecules into centrosymmetric R(2) (2)(18) dimers. These dimers are connected via a C-H?? contact between the 2-methyl-phenyl and trimethoxy-phenyl rings, and a ?-? contact between the thia-diazole and trimethoxy-phenyl rings [interplanar distance 3.51?Å, dihedral angles 4.17(4)°]. An intramolecular C-H?N hydrogen bond is also present.

| S-EPMC2962111 | biostudies-literature

6-(4-Pyrid-yl)-3-(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the mol-ecule of the title compound, C(17)H(15)N(5)O(3)S, the planar central heterocylic ring system is oriented at dihedral angles of 5.32?(4) and 9.41?(4)°, respectively with respect to trimethoxy-phenyl and pyridine rings. Intra-molecular C-H?N, C-H?O and C-H?S hydrogen bonds result in the formation of a nearly planar six-membered ring, which is oriented at a dihedral angle of 3.07?(5)° with respect to the central heterocylic ring system, and non-planar six- and five-membered rings having twist and envelope conformations, respectively. In the crystal structure, inter-molecular C-H?N and C-H?O hydrogen bonds link the mol-ecules. There is a C-H?? contact between the pyridine ring and a methyl group and a ?-? contact between the central heterocylic ring system and the trimethoxy-phenyl ring [centroid-centroid distance = 3.758?(1)?Å].

| S-EPMC2962241 | biostudies-literature

6-(3-Pyrid-yl)-3-(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the mol-ecule of the title compound, C(17)H(15)N(5)O(3)S, the planar central heterocylic ring system is oriented with respect to the benzene and pyridine rings at dihedral angles of 6.61?(3) and 19.22?(3)°, respectively. An intra-molecular C-H?N hydrogen bond results in the formation of a six-membered ring, adopting a flattened boat conformation. In the crystal structure, inter-molecular C-H?N hydrogen bonds link the mol-ecules.

| S-EPMC2962035 | biostudies-literature

3-Ethyl-6-{1-[4-(2-methyl-prop-yl)phen-yl]eth-yl}-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the mol-ecule of the title compound, C(17)H(22)N(4)S, the triazolothia-diazole ring system is essentially planar and forms a dihedral angle of 74.34?(6)° with the benzene ring. In the crystal structure, mol-ecules are linked into chains running along the b axis by C-H?? inter-actions; adjacent chains are cross-linked via C-H?N hydrogen bonds and short S?N contacts [3.2694?(14) and 3.2953?(14)?Å].

| S-EPMC2960717 | biostudies-literature

4-Bromo-benzoic acid-6-(4-bromo-phen-yl)-3-methyl-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole (1/1).

Project description:In the title 1:1 co-crystal, C(10)H(7)BrN(4)S·C(7)H(5)BrO(2), the triazolothia-diazole system is approximately planar [with a maximum deviation of 0.030?(4)?Å] and forms a dihedral angle of 8.6?(1)° with the bromo-phenyl ring. In the carb-oxy-lic acid mol-ecule, the carboxyl group is rotated by 6.4?(3)° out of the benzene ring plane. The crystal structure features O-H?N and C-H?O hydrogen bonds, ?-? stacking inter-actions [centroid-centroid distances = 3.713?(2), 3.670?(2) and 3.859?(3)?Å] and short S?N [2.883?(4)?Å] contacts.

| S-EPMC3344123 | biostudies-literature

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