title: (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.
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-dihydropyrimidine monohydrate, 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.
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India.
authors.forename: Prakash S
authors.initials: PS
authors.lastname: Nayak
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India.
authors.forename: Badiadka
authors.initials: B
authors.lastname: Narayana
authors.affiliation: University of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India.
authors.forename: Hemmige S
authors.initials: HS
authors.lastname: Yathirajan
authors.affiliation: Department of Chemistry, Nelson Mandela Metropolitan University, Summerstrand Campus (South), University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa.
authors.forename: Eric C
authors.initials: EC
authors.lastname: Hosten
authors.affiliation: Department of Chemistry, Nelson Mandela Metropolitan University, Summerstrand Campus (South), University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa.
authors.forename: Richard
authors.initials: R
authors.lastname: Betz
authors.affiliation: School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D018360:Crystallography, X-Ray; D019791:Guanidine / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C000596739:2-amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidine monohydrate; C000596738:3-(6-methoxynaphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one; D009281:Naphthalenes; D011725:Pyridines; D011743:Pyrimidines; D019791:Guanidine
keywords: 3,4-dihydropyrimidine; Claisen condensation; chalcones; crystal structure; cyclocondensation; hydrogen bonding; prop-2-en-1-one