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(1E,4E)-1,5-Bis(4-methyl-phen-yl)penta-1,4-dien-3-one.

ABSTRACT: The title compound, C(19)H(18)O, crystallizes in a non-centrosymmetric space group although the mol-ecule has no chiral centre. The dihedral angle between the aromatic rings is 20.43?(13)°. The structure is stabilized by two intra-molecular hydrogen bonds, and by four ?-? and three C-H?? inter-actions between the aromatic rings. The perpendicular distances between the centroids of the rings involved in the ?-? inter-actions have values of 1.996, 2.061, 2.181 and 2.189?Å.

SUBMITTER: Arshad MN

PROVIDER: S-EPMC2962047 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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(1E,4E)-1,5-Bis(4-methyl-phen-yl)penta-1,4-dien-3-one.

Arshad Muhammad Nadeem MN Tahir Muhammad Nawaz MN Asghar Muhammad Nadeem MN Khan Islam Ullah IU Ashfaq Muhammad M

Acta crystallographica. Section E, Structure reports online 20080705 Pt 8

The title compound, C(19)H(18)O, crystallizes in a non-centrosymmetric space group although the mol-ecule has no chiral centre. The dihedral angle between the aromatic rings is 20.43 (13)°. The structure is stabilized by two intra-molecular hydrogen bonds, and by four π-π and three C-H⋯π inter-actions between the aromatic rings. The perpendicular distances between the centroids of the rings involved in the π-π inter-actions have values of 1.996, 2.061, 2.181 and 2.189 Å. ...[more]

PMID: 21203132

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(1E,4E)-1,5-Bis(2,4,5-trimethoxy-phen-yl)penta-1,4-dien-3-one.

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(1E,4E)-1-(3-Nitro-phen-yl)-5-phenyl-penta-1,4-dien-3-one.

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Crystal structures of (1E,4E)-1,5-bis-(5-bromo-thio-phen-2-yl)-2,4-di-methyl-penta-1,4-dien-3-one and (E)-4-(5-bromo-thio-phen-2-yl)-1,3-di-phenyl-but-3-en-2-one.

Project description:The title compounds, C15H12Br2OS2, (I), and C20H15BrOS, (II), were synthesized by employing Claisen-Schmidt condensation of pentan-3-one and di-benzyl-acetone with 5-bromo-thio-phene-2-carbaldehyde in the presence of methano-lic KOH. Even though 1:2 products were expected in both of the reactions, 1:2 and 1:1 products were obtained as (I) and (II), respectively. In (I), the two methyl groups are trans to each other, 29.5 (7) and 28.7 (7)° away from the central carbonyl bond between them, whereas the two phenyl rings of di-benzyl-acetone subtend a dihedral angle of 53.09 (18)°. In the crystal of (I), C-H⋯O hydrogen bonds define mol-ecular chains along c. A second type of mol-ecular chain is formed along b by means of C-Br⋯π inter-actions. These two families of mol-ecular chains are stacked by π-π inter-actions, forming a three-dimensional supra-molecular architecture. In (II), similar C-H⋯O hydrogen bonds as in (I) define inversion dimers, whilst C-H⋯.π inter-actions build a staircase structure along the a axis.

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Crystal structure of benzyl N'-[(1E,4E)-1,5-bis-(4-meth-oxy-phen-yl)penta-1,4-dien-3-yl-idene]hydrazine-1-carbodi-thio-ate.

Project description:In the title hydrazinecarbodi-thio-ate derivative, C27H26N2O2S2, the asymmetric unit is comprised of four mol-ecules (Z = 8 and Z' = 4). The 4-meth-oxy-phenyl rings are slightly twisted away from their attached olefinic double bonds [torsion angles = 5.9 (4)-19.6 (4)°]. The azomethine double bond has an s-trans configuration relative to one of the C=C bonds and an s-cis configuration relative to the other [C=C-C= N = 147.4 (6)-175.7 (2) and 15.3 (3)-37.4 (7)°, respectively]. The torsion angles between the azomethine C=N double bond and hydrazine-1-carbodi-thio-ate moiety indicate only small deviations from planarity, with torsion angles ranging from 0.9 (3) to 6.9 (3)° and from 174.9 (3) to 179.7 (2)°, respectively. The benzyl ring and the methyl-enesulfanyl moiety are almost perpendicular to each other, as indicated by their torsion angles [range 93.7 (3)-114.6 (2)°]. In the crystal, mol-ecules are linked by C-H⋯O, N-H⋯S and C-H⋯π(ring) hydrogen-bonding inter-actions into a three-dimensional network. Structural details of related benzyl hydrazine-1-carbodi-thio-ate are surveyed and compared with those of the title compound.

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