TY - JOUR
T1 - (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
T2 - two types of hydrogen-bonded sheet
AU - Nayak, Prakash S.
AU - Narayana, Badiadka
AU - Yathirajan, Hemmige S.
AU - Hosten, Eric C.
AU - Betz, Richard
AU - Glidewell, Christopher
PY - 2014/11
Y1 - 2014/11
N2 - 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.
AB - 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.
KW - Crystal structure
KW - Hydrogen bonding
KW - Chalcones
KW - Cyclocondensation
KW - prop-2-en-1-one
KW - 3,4-dihydropyrimidine
KW - Claisen condensation
KW - Intramolecular motions
KW - Phenylphosphonic acid
KW - BIological-activity
KW - CP/MAS NMR
KW - 4,4'-sulfonyldiphenol
KW - 4,4'-THIODIPHENOL
KW - Anticancer
KW - Bromides
KW - Adducts
U2 - 10.1107/S2053229614021524
DO - 10.1107/S2053229614021524
M3 - Article
SN - 0108-2701
VL - 70
SP - 1011
EP - 1016
JO - Acta Crystallographica Section C: Crystal Structure Communications
JF - Acta Crystallographica Section C: Crystal Structure Communications
IS - 11
ER -