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1-Benzyl-3,5-bis-[(E)-3-thienyl-methyl-idene]piperidin-4-one.

ABSTRACT: In the title mol-ecule, C(22)H(19)NOS(2), the piperidine ring adopts an envelope conformation with the benzyl substituent in an equatorial position. Each of the olefinic double bonds has an E configuration. The dihedral angle between the two thio-phene rings is 1.55?(18)°. The thio-phene rings form angles of 72.21?(14) and 73.43?(14)° with the phenyl ring. Both thio-phene rings are disordered over two orientations [occupancy ratios of 0.799?(1):0.201?(1)] at 180° from one another. In the crystal, weak inter-molecular C-H?O hydrogen bonds and C-H?? inter-actions help to stabilize the packing.

SUBMITTER: Gayathri P

PROVIDER: S-EPMC3052058 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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1-Benzyl-3,5-bis-[(E)-3-thienyl-methyl-idene]piperidin-4-one.

Gayathri P P Thiruvalluvar A A Rajeswari K K Pandiarajan K K Butcher R J RJ

Acta crystallographica. Section E, Structure reports online 20110205 Pt 3

In the title mol-ecule, C(22)H(19)NOS(2), the piperidine ring adopts an envelope conformation with the benzyl substituent in an equatorial position. Each of the olefinic double bonds has an E configuration. The dihedral angle between the two thio-phene rings is 1.55 (18)°. The thio-phene rings form angles of 72.21 (14) and 73.43 (14)° with the phenyl ring. Both thio-phene rings are disordered over two orientations [occupancy ratios of 0.799 (1):0.201 (1)] at 180° from one another. In the crystal ...[more]

PMID: 21522333

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Project description:In the title mol-ecule, C(18)H(19)NOS(2)·H(2)O, the piperidine ring adopts an envelope conformation with the methyl substituent in an equatorial position. Each of the olefinic double bonds has an E configuration. The dihedral angle between the two thio-phene rings is 6.04 (14)°. The water mol-ecule forms two donor inter-actions, one with the carbonyl O atom and the other to the hetero N atom. The centrosymmetric {C(18)H(19)NOS(2)·H(2)O}(2) pairs thus formed are linked into a supra-molecular chain via C-H⋯O(water) contacts.

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Crystal structures of 3,5-bis-[(E)-3-hy-droxy-benzyl-idene]-1-methyl-piperidin-4-one and 3,5-bis-[(E)-2-chloro-benzyl-idene]-1-methyl-piperidin-4-one.

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(3E,5E)-3,5-Bis(2-chloro-benzyl-idene)-1-propyl-piperidin-4-one.

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(3E,5E)-1-Allyl-3,5-bis(4-meth-oxy-benzyl-idene)-piperidin-4-one.

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(3E,5E)-1-Acryloyl-3,5-bis-(2,4-dichloro-benzyl-idene)piperidin-4-one hemihydrate.

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