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

ABSTRACT: 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.

SUBMITTER: Aridoss G

PROVIDER: S-EPMC2959549 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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

Aridoss G G Amirthaganesan S S Velmurugan D D Kim S H SH Jeong Y T YT

Acta crystallographica. Section E, Structure reports online 20081011 Pt 11

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. ...[more]

PMID: 21580960

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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.

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

Project description: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.

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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.

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(±)-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.

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(2R)-2-Cinnamoylamino-N-[5-(4-methoxy-phen-yl)-1,3,4-thia-diazol-2-yl]propanamide.

Project description:The asymmetric unit of the title compound, C(21)H(20)N(4)O(3)S, contains two independent mol-ecules. The dihedral angles between the two benzene rings are 47.6?(1) and 30.2?(1)°, the corresponding values between the p-methoxy-benzene and thia-diazol rings are 12.3?(1) and 24.7?(1)°, respectively, for the two mol-ecules. The conformations of the N-H and C=O bonds are anti with respect to each other. The enone groups show a trans configuration. The crystal structure is stabilized by N-H?O and N-H?N inter-actions. The absolute structure could not be determined from the X-ray data but the absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.

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2-(2,4-Dichloro-phen-yl)-3-[5-(4-methoxy-phen-yl)-1,3,4-thia-diazol-2-yl]-1,3-thia-zolidin-4-one.

Project description:In the mol-ecule of the title compound, C(18)H(13)Cl(2)N(3)O(2)S(2), the thia-zolidinone ring has an envelope conformation with the S atom displaced by 0.394?(3)?Å from the plane of the other ring atoms. The thia-diazole ring is oriented at a dihedral angle of 7.40?(4)° with respect to the 4-methoxy-phenyl ring. Intra-molecular C-H?S, C-H?N and C-H?Cl hydrogen bonds result in the formation of two planar and two non-planar five-membered rings. The planar five-membered rings are oriented at a dihedral angle of 6.23?(3)°. The 2,4-dichloro-phenyl ring is oriented at dihedral angles of 84.21?(4) and 83.55?(3)° with respect to the thia-diazole and 4-methoxy-phenyl rings, respectively. In the crystal structure, inter-molecular C-H?O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

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3-[5-(4-Fluoro-phen-yl)-1,3,4-thia-diazol-2-yl]-2-(4-methoxy-phen-yl)-1,3-thia-zolidin-4-one.

Project description:The title compound, C(18)H(14)FN(3)O(2)S(2), was synthesized by the reaction of 5-(4-fluoro-phen-yl)-N-(4-methoxy-benzyl-idene)-1,3,4-thia-diazol-2-amine and mercaptoacetic acid. The thia-zolidinone ring adopts a twist conformation. The 4-methoxy-phenyl ring is almost perpendicular to the thia-diazole ring, making a dihedral angle of 88.4?(3)°. The 4-fluoro-phenyl ring is nearly coplanar with the thia-diazole ring, the dihedral angle being 6.8?(3)°. The crystal structure involves C-H?N, C-H?O and C-H?S hydrogen bonds.

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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-(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].

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