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3,5-Bis(4-chloro-benzyl-idene)-1-methyl-piperidin-4-one.

ABSTRACT: In the title mol-ecule, C(20)H(17)Cl(2)NO, the central heterocyclic ring adopts a flattened boat conformation. The dihedral angles between the planar part of this central heterocyclic ring [maximum deviation = 0.004?(1)?Å] and the two almost planar side-chain fragments [maximum deviations = 0.015?(1) and 0.019?(1)?Å], that include the aromatic ring and bridging atoms, are 18.1?(1) and 18.0?(1)°. In the crystal, pairs of weak inter-molecular C-H?O hydrogen bonds link mol-ecules into inversion dimers that form stacks along the a axis. The structure is further stabilized by weak inter-molecular C-H?? inter-actions involving the benzene rings.

SUBMITTER: Nesterov VV

PROVIDER: S-EPMC3099892 | biostudies-other | 2011 Apr

REPOSITORIES: biostudies-other

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3,5-Bis(4-chloro-benzyl-idene)-1-methyl-piperidin-4-one.

Nesterov Volodymyr V VV Sarkisov Sergey S SS Shulaev Vladimir V Nesterov Vladimir N VN

Acta crystallographica. Section E, Structure reports online 20110302 Pt 4

In the title mol-ecule, C(20)H(17)Cl(2)NO, the central heterocyclic ring adopts a flattened boat conformation. The dihedral angles between the planar part of this central heterocyclic ring [maximum deviation = 0.004 (1) Å] and the two almost planar side-chain fragments [maximum deviations = 0.015 (1) and 0.019 (1) Å], that include the aromatic ring and bridging atoms, are 18.1 (1) and 18.0 (1)°. In the crystal, pairs of weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into inversion dim ...[more]

PMID: 21754057

Similar Datasets

1-Benzyl-3,5-bis-(4-chloro-benzyl-idene)piperidin-4-one.

Project description:The title compound, C(26)H(21)Cl(2)NO, crystallizes with two symmetry-independent mol-ecules (A and B) in the asymmetric unit. In both mol-ecules, the central heterocyclic ring adopts a sofa conformation. The dihedral angles between the planar part of this central heterocyclic ring [maximum deviations of 0.011?(1) and 0.036?(1)?Å in mol-ecules A and B, respectively] and the two almost planar [maximum deviations of 0.020?(1) and 0.008?(1)?Å in A and 0.007?(1) and 0.011?(1) in B] side-chain fragments that include the aromatic ring and bridging atoms are 20.1?(1) and 31.2?(1)° in mol-ecule A, and 26.4?(1) and 19.6?(1)° in mol-ecule B. The dihedral angles between the planar part of the heterocyclic ring and the benzyl substituent are 79.7?(1) and 53.2?(1)° in mol-ecules A and B, respectively. In the crystal, weak inter-molecular C-H?O hydrogen bonds link the two independent mol-ecules into dimers.

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

Project description: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.

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Project description:In the title compound, C(22)H(17)Cl(2)NO(2), the asymmetric unit consists of two crystallographically independent mol-ecules and each piperidinone ring adopts an envelope conformation. The dihedral angles between the two chloro-benzene rings are 24.81?(10) and 19.15?(8)° in the two mol-ecules. In the crystal, mol-ecules are connected via weak inter-molecular C-H?O hydrogen bonds forming layers perpendicular to the a axis.

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

Project description:The title compound, C22H21Cl2NO, is a derivative of mono-carbonyl analogues of curcumin (MACs). The mol-ecule has an E conformation for each of the olefinic bonds. The 1-propyl-piperidin-4-one ring has a distorted chair conformation with the ring N and the C and O atoms of the carbonyl group deviating from the mean plane of the remaining four ring C atoms by 0.682?(2), -0.134?(3) and -0.340?(4)?Å, respectively. The dihedral angle between the benzene rings is 26.5?(1)°. In the crystal, mol-ecules are connected by weak C-H?O and C-H?? inter-actions.

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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.

Project description:The title compounds, C20H19NO3, (1), and C20H17Cl2NO, (2), are the 3-hy-droxy-benzyl-idene and 2-chloro-benzyl-idene derivatives, respectively, of curcumin [systematic name: (1E,6E)-1,7-bis-(4-hy-droxy-3-meth-oxy-phen-yl)-1,6-hepta-diene-3,5-dione]. The dihedral angles between the benzene rings in each compound are 21.07?(6)° for (1) and 13.4?(3)° for (2). In both compounds, the piperidinone rings adopt a sofa confirmation and the methyl group attached to the N atom is in an equatorial position. In the crystal of (1), two pairs of O-H?N and O-H?O hydrogen bonds link the mol-ecules, forming chains along [10-1]. The chains are linked via C-H?O hydrogen bonds, forming undulating sheets parallel to the ac plane. In the crystal of (2), mol-ecules are linked by weak C-H?Cl hydrogen bonds, forming chains along the [204] direction. The chains are linked along the a-axis direction by ?-? inter-actions [inter-centroid distance = 3.779?(4)?Å]. For compound (2), the crystal studied was a non-merohedral twin with the refined ratio of the twin components being 0.116?(6):0.886?(6).

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(3E,5E)-3,5-Bis(4-methyl-benzyl-idene)-1-[3-(piperidin-1-yl)propano-yl]piperidin-4-one.

Project description:In the title compound, C(29)H(34)N(2)O(2), the central piperidine ring adopts a half-chair conformation, whereas the terminal one adopts a chair conformation. The mean plane of the central piperidine ring [maximum deviation = 0.384 (2) Å] makes dihedral angles of 64.82 (13) and 17.55 (13)° with the benzene rings. In the crystal, mol-ecules are linked into a tape along the b axis via C-H⋯O inter-actions, generating R(2) (2)(20) and R(2) (1)(6) graph-set motifs. C-H⋯π inter-actions are observed between the tapes.

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(3E,5E)-1-Benzyl-3,5-bis-(2-fluoro-benzyl-idene)piperidin-4-one.

Project description:The inversion-related mol-ecules of the title compound, C(26)H(21)F(2)NO, associate into closed dimeric subunits via co-operative C-H⋯π inter-actions. Two non-classical C-H⋯O and one C-H⋯N intra-molecular hydrogen bonds are also found in the crystal structure. The piperidin-4-one ring adopts a sofa conforamtion with the 1-benzyl group in the equatorial position, and the equiplanar fluoro-phenyl substituents in the 3- and 5-positions stretched out on either side. The 1-benzyl group is disposed towards the substituent in the 6th position of the piperidin-4-one ring. The 3,5-diene units possess E configurations.

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

Project description:The piperidine ring in the title compound, C24H25NO3, adopts an envelope conformation with the N atom being the flap atom, and each C=C double bond exhibits an E conformation. In the crystal, C-H?O hydrogen bonds link the mol-ecules, forming supramolecular layers that stack along the a axis.

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

Project description:The asymmetric unit of the title compound, C(22)H(15)Cl(4)NO(2)·0.5H(2)O, consists of a (3E,5E)-1-acryloyl-3,5-bis-(2,4-dichloro-benzyl-idene)piperidin-4-one mol-ecule and a half-mol-ecule of water (the O atom of the water mol-ecule lies on a twofold axis). The piperidin-4-one ring adopts an envelope conformation. The dihedral angle between the two terminal benzene rings is 8.84?(11)°. In the crystal, mol-ecules are connected by C-H?O hydrogen bonds forming supra-molecular chains along the c axis. Furthermore, adjacent chains are inter-connected by the water mol-ecules via O-H?O hydrogen bonds.

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(3E,5E)-3,5-Bis(4-allyl-oxybenzyl-idene)-1-benzyl-piperidin-4-one.

Project description:In the title compound C(32)H(31)NO(3), the all-yloxy groups on either side of the piperidin-4-one ring are conformationally disordered. The contribution of major and minor components of the allyloxy group at the 3rd position of the ring are 0.576?(4) and 0.424?(4), respectively, and those at the 5th position are 0.885?(3) and 0.115?(3), respectively. The six-membered piperidin-4-one ring adopts a sofa conformation with the benzyl group occupying an equatorial position and the olefinic double bonds possessing an E configuration. Flanking phenyl substituents are stretched out on either side of the six-membered ring. ?-? inter-actions with a centroid-centroid distance of 3.885?(1)?Å give rise to mol-ecular dimers and short C-H?? contacts lead to chains along the c axis.

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