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N-[4-Acetyl-5-(2-methylprop-1-enyl)-5-(2-p-tolyl-prop-yl)-4,5-dihydro-1,3,4-thia-diazol-2-yl]acetamide.

ABSTRACT: The title heterocyclic compound, C(20)H(27)N(3)O(2)S, was synthesized from 2-(4-methyl-cyclo-hex-3-en-yl)-6-methyl-hepta-2,5-dien-4-one, which was isolated from the essential oil Cedrus atlantica. The thia-diazole ring is essentially planar [maximum deviation 0.006?(2)?Å] and it forms a dihedral angle of 18.08?(9)° with the benzene ring. The dihedral angle between the thia-diazole ring and the acetamide plane is 7.62?(10)°. In the crystal, mol-ecules are linked into chains running along the c axis by inter-molecular N-H?O hydrogen bonds.

SUBMITTER: Mazoir N

PROVIDER: S-EPMC2969617 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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N-[4-Acetyl-5-(2-methylprop-1-enyl)-5-(2-p-tolyl-prop-yl)-4,5-dihydro-1,3,4-thia-diazol-2-yl]acetamide.

Mazoir Noureddine N El Ammari Lahcen L Bouhmaida Nouzha N Dahaoui Slimane S Benharref Ahmed A Berraho Moha M

Acta crystallographica. Section E, Structure reports online 20090514 Pt 6

The title heterocyclic compound, C(20)H(27)N(3)O(2)S, was synthesized from 2-(4-methyl-cyclo-hex-3-en-yl)-6-methyl-hepta-2,5-dien-4-one, which was isolated from the essential oil Cedrus atlantica. The thia-diazole ring is essentially planar [maximum deviation 0.006 (2) Å] and it forms a dihedral angle of 18.08 (9)° with the benzene ring. The dihedral angle between the thia-diazole ring and the acetamide plane is 7.62 (10)°. In the crystal, mol-ecules are linked into chains running along the c ax ...[more]

PMID: 21583133

Similar Datasets

N-[4-Acetyl-5-methyl-5-(2-p-tolyl-prop-yl)-4,5-dihydro-1,3,4-thia-diazol-2-yl]acetamide.

Project description:The title heterocyclic compound, C(17)H(23)N(3)O(2)S, was synthesized from 4-(4-methyl-cyclo-hex-3-en-yl)pent-3-en-2-one, which was isolated from Cedrus atlantica essential oil. The thia-diazole ring adopts a flattened envelope conformation, with the flap sp(3)-hybridized C atom lying 0.259?(1)?Å out of the plane of the other four atoms. The screw-related mol-ecules are linked into chains along the b axis by inter-molecular N-H?O hydrogen bonds.

| S-EPMC2968392 | biostudies-other

N-[4-Acetyl-5-(3-methoxy-phen-yl)-4,5-dihydro-1,3,4-thia-diazol-2-yl]acetamide.

Project description:The title compound, C(13)H(15)N(3)O(3)S, crystallizes with two mol-ecules in the asymmetric unit. The thia-diazole rings in both the mol-ecules adopt an envelope conformation. The crystal packing is stabilized by inter-molecular N-H?O and C-H?O inter-actions.

| S-EPMC2959549 | biostudies-literature

N-(5-Sulfanyl-idene-4,5-dihydro-1,3,4-thia-diazol-2-yl)acetamide dimethyl sulfoxide disolvate.

Project description:In the title compound, C(4)H(5)N(3)OS(2)·2C(2)H(6)OS, the five-membered heterocyclic ring and the N-(C=O)-C plane of the acetamide group are essentially co-planar, with a dihedral angle of 1.25?(3)°. Inter-molecular N-H?O hydrogen bonds between the acetamide compound and the dimethyl sulfoxide mol-ecules stabilize the crystal structure. The two dimethyl sulfoxide mol-ecules are each disordered over two positions with occupancy ratios of 0.605?(2):0.395?(2) and 0.8629?(18):0.1371?(18).

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N-[4-Acetyl-5-isobutyl-5-(2-p-tolyl-prop-yl)-4,5-dihydro-1,3,4-thia-diazol-2-yl]acetamide ethyl acetate hemisolvate.

Project description:The racemic title compound, a new terpenoid, C(20)H(29)N(3)O(2)S·0.5C(4)H(8)O(2), was synthesized from Cedrus Atlantica essential oil. The compound crystallizes with a disordered ethyl acetate solvent mol-ecule. The thia-diazole ring is almost planar, with a maximum deviation from the mean plane of 0.015?(2)?Å for the C atom connected to the isobutyl group and has a puckering amplitude of 0.026?(2)?Å. The dihedral angle between the benzene and thia-diazole rings is 18.32?(8)°. The crystal packing involves inter-molecular N-H?O hydrogen bonds.

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N-[4-Acetyl-5-(4-fluoro-phen-yl)-4,5-di-hydro-1,3,4-thia-diazol-2-yl]acetamide.

Project description:The title mol-ecule, C12H12FN3O2S, shows a short intra-molecular S?O contact of 2.682?(18)?Å. The dihedral angle between the thia-diazole ring and the benzene ring is 86.82?(11)°. In the crystal, N-H?O and C-H?O hydrogen bonds generate an R 2 (1)(6) graph-set motif between adjacent mol-ecules. Pairs of futher C-H?O hydrogen bonds form inversion dimers with R 2 (2)(8) ring motifs. These combine to generate a three-dimensional network and stack the mol-ecules along the b axis.

| S-EPMC3648237 | biostudies-literature

N-(5-Methyl-sulfanyl-1,3,4-thia-diazol-2-yl)acetamide.

Project description:In the title compound, C(5)H(7)N(3)OS(2), inversion dimers linked by pairs of N-H⋯N hydrogen bonds occur, forming R(2) (2)(8) ring motifs. These dimers are arranged into chains via inter-molecular C-H⋯O hydrogen bonds between the methylsulfanyl groups and the O atoms of the carbonyl groups. The acetamido-1,3,4-thio-diazole unit is essentially planar [r.m.s. deviation 0.045 (8) Å].

| S-EPMC2969935 | biostudies-literature

N-(5-Benzyl-sulfanyl-1,3,4-thia-diazol-2-yl)-2-(piperidin-1-yl)acetamide.

Project description:The title compound, C16H20N4OS2, was synthesized by the reaction of 2-benzyl-sulfanyl-5-chloro-acetamido-1,3,4-thia-diazole and piperidine in a 1:2 ratio. The planes of the acetamide and 1,3,4-thia-diazole units are twisted by 10.8 (4)°. The thia-diazole S atom and the acetamide O atom are syn-oriented due to a hypervalent S⋯O inter-action of 2.628 (4) Å. In the crystal, mol-ecules form centrosymmetric dimers via N-H⋯N hydrogen bonds. These dimers are further connected by C-H⋯O inter-actions into (100) layers.

| S-EPMC3998473 | biostudies-literature

(±)-N-[4-Acetyl-5-methyl-5-(4-methyl-cyclo-hex-3-en-yl)-4,5-dihydro-1,3,4-thia-diazol-2-yl]acetamide.

Project description:The new title thiadiazole compound, C(14)H(21)N(3)O(2)S, was semi-synthesized starting from 1-(4-methyl-cyclo-hex-3-en-yl)ethanone, a natural product isolated from Cedrus atlantica essential oil. The stereochemistry has been confirmed by single-crystal X-ray diffraction. The thia-diazo-line ring is roughly planar, although it may be regarded as having a half-chair conformation. The cyclo-hexenyl ring has a half-chair conformation. The most inter-esting feature is the formation of a pseudo-ring formed by four mol-ecules associated through N-H?O hydrogen bonds around a fourfold inversion axis, forming an R(4) (4)(28) motif.

| S-EPMC2960842 | biostudies-other

5-({3-[(5-Amino-1,3,4-thia-diazol-2-yl)sulfanylmeth-yl]benz-yl}sulfan-yl)-1,3,4-thia-diazol-2-amine.

Project description:In the title compound, C(12)H(12)N(6)S(4), the two terminal thia-diazole 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 thia-diazole rings is 27.77?(4)°. Inter-molecular N-H?N hydrogen bonds stabilize the crystal packing, linking the mol-ecules into a tape along the b axis.

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5-(3-Pyrid-yl)-1,3,4-thia-diazol-2-amine.

Project description:The title compound, C(7)H(6)N(4)S, was synthesized by reacting pyridine-3-carboxylic acid and thio-semicarbazide. The dihedral angle between the planes of the thia-diazole and pyridine rings is 32.42?(14)°. In the crystal structure, inter-molecular N-H?N inter-actions link the mol-ecules into a three-dimensional network, forming R(2) (2)(8) ring motifs. ?-? contacts between thia-diazole rings [centroid-centroid distance = 3.666?(1)?Å] may further stabilize the structure.

| S-EPMC2969629 | biostudies-literature

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