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Eryanti Y, Zamri A, Herlina T, et al. 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. Acta Crystallogr E Crystallogr Commun. 2015;71:1488-92doi: 10.1107/S2056989015020976.
Eryanti, Y., Zamri, A., Herlina, T., Supratman, U., Rosli, M. M., & Fun, H. K. (2015). 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. Acta crystallographica. Section E, Crystallographic communications, 711488-92. https://doi.org/10.1107/S2056989015020976
Eryanti, Yum, et al. "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." Acta crystallographica. Section E, Crystallographic communications vol. 71 (2015): 1488-92. doi: https://doi.org/10.1107/S2056989015020976
Eryanti Y, Zamri A, Herlina T, Supratman U, Rosli MM, Fun HK. 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. Acta Crystallogr E Crystallogr Commun. 2015 Nov 11;71:1488-92. doi: 10.1107/S2056989015020976. eCollection 2015 Dec 01. PMID: 26870411; PMCID: PMC4719820.
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Acta Crystallogr E Crystallogr Commun. 2015 Nov 11;71:1488-92. doi: 10.1107/S2056989015020976. eCollection 2015 Dec 01.

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.

Acta crystallographica. Section E, Crystallographic communications

Yum Eryanti, Adel Zamri, Tati Herlina, Unang Supratman, Mohd Mustaqim Rosli, Hoong-Kun Fun

Affiliations

  1. Laboratory of Organic Synthesis, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Riau University, Pekanbaru 26293, Indonesia.
  2. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jalan Raya Bandung-Sumedang Km 21, Jatinangor 45363, Sumedang, Indonesia.
  3. Department of Chemistry, Faculty of Mathematics and Narural Sciences, Padjadjaran University, Jalan Raya Bandung-Sumedang Km 21, Jatinangor 45363, Sumedang, Indonesia.
  4. X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
  5. X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia; Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.

PMID: 26870411 PMCID: PMC4719820 DOI: 10.1107/S2056989015020976

Abstract

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 π-π 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).

Keywords: benzyl­idene; crystal structure; hydrogen bonding; methyl­piperidin-4-one; piperidinone

References

  1. Bioorg Med Chem. 2013 Jun 1;21(11):3058-65 - PubMed
  2. Acta Crystallogr D Biol Crystallogr. 2009 Feb;65(Pt 2):148-55 - PubMed
  3. Mol Cell Biochem. 2009 Nov;331(1-2):127-33 - PubMed
  4. Crit Care Med. 2006 Jul;34(7):1874-82 - PubMed
  5. Eur J Med Chem. 2013 Feb;60:1-9 - PubMed
  6. Arch Pharm (Weinheim). 2009 Oct;342(10):584-90 - PubMed
  7. Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8 - PubMed
  8. J Enzyme Inhib Med Chem. 2012 Apr;27(2):267-74 - PubMed
  9. Acta Crystallogr Sect E Struct Rep Online. 2011 Apr 1;67(Pt 4):o760-1 - PubMed
  10. Biol Pharm Bull. 2005 Aug;28(8):1438-43 - PubMed
  11. Bioorg Med Chem. 2010 Sep 15;18(18):6701-7 - PubMed
  12. Angew Chem Int Ed Engl. 2014 Jan 13;53(3):662-71 - PubMed
  13. Anticancer Res. 2003 Jan-Feb;23(1A):363-98 - PubMed
  14. Eur J Med Chem. 2010 Dec;45(12):5773-80 - PubMed
  15. Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22 - PubMed
  16. Bioorg Med Chem Lett. 2007 Dec 1;17(23):6459-62 - PubMed

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