(2E)-3-(6-Methoxynaphthalen-2-yl)1-(pyridin-3-yl)prop-2-en-1-one and its cyclocondensation product with guanidine, (4RS)-2-amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidine monohydrate: two types of hydrogen-bonded sheet

Prakash S. Nayak, Badiadka Narayana, Hemmige S. Yathirajan, Eric C. Hosten, Richard Betz*, Christopher Glidewell

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The structures of a chalcone and of its cyclocondensation product with guanidine are reported. In (2E)-3-(6-methoxynaphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one, C19H15NO2, (I), the planes of the pyridine and naphthalene units make dihedral angles with that of the central spacer unit of 23.61 (13) and 23.57 (15)°, respectively, and a dihedral angle of 47.24 (9)° with each other. The molecules of (I) are linked into sheets by a combination of C—H…O and C—H…π(arene) hydrogen bonds. In the cyclocondensation product (4RS)-2-amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidinemonohydrate, C20H18N4O·H2O, (II), the dihydropyrimidine ring adopts a conformation best described as a shallow boat. The molecular components are linked by two N—H…O hydrogen bonds, two O—H…N hydrogen bonds and one N—H…N hydrogen bond to form complex sheets, with the methoxynaphthalene interdigitated between inversion-related pairs of sheets.

Original languageEnglish
Pages (from-to)1011-1016
Number of pages15
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume70
Issue number11
DOIs
Publication statusPublished - Nov 2014

Keywords

  • Crystal structure
  • Hydrogen bonding
  • Chalcones
  • Cyclocondensation
  • prop-2-en-1-one
  • 3,4-dihydropyrimidine
  • Claisen condensation
  • Intramolecular motions
  • Phenylphosphonic acid
  • BIological-activity
  • CP/MAS NMR
  • 4,4'-sulfonyldiphenol
  • 4,4'-THIODIPHENOL
  • Anticancer
  • Bromides
  • Adducts

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