TY - JOUR
T1 - Mechanochemical Complexation of Diethyl N,Ń-[1,3-(2-methyl)phenyl]dioxalamate and Resorcinol
T2 - Conformational Twist and X-Ray Helical Supramolecular Architecture
AU - González-González, Juan Saulo
AU - Zúñiga-Lemus, Oscar
AU - Martínez-Martínez, Francisco J.
AU - Gonzalez, Jorge
AU - García-Báez, Efrén V.
AU - Padilla-Martínez, Itzia I.
N1 - Publisher Copyright:
© 2015 Springer Science+Business Media New York.
PY - 2015/5/22
Y1 - 2015/5/22
N2 - The cocrystal formed by diethyl N,Ń-[1,3-(2-methyl)phenyl]dioxalamate (1) and resorcinol (2), namely 1·2cryst (C21H24N2O8) was prepared by mechanochemical complexation. IR spectroscopy and powder X-ray diffraction studies allowed to determine the complexation and the conformational switching of the ethyl oxalamate side arms. In the crystal structure of 1·2cryst, complexation occurs through O-H···O=C hydrogen-bonding interactions with the participation of phenolic O-H as donor and amide carbonyl group as acceptor. The steric hindrance of the CH3 group in the C-2 position of the aromatic ring leads to a meso-helical supramolecular architecture forming a C22 (16) chain motif. Crystal data: monoclinic, C2/c space group, a = 34.9054(13) Å, b = 8.0434(5) Å, c = 5.1577(8) Å, β = 97.521(3)°. Graphical Abstract: The cocrystal formed by diethyl N,N'-[1,3-(2-methyl)phenyl]dioxalamate and resorcinol, prepared by mechanochemical complexation.
AB - The cocrystal formed by diethyl N,Ń-[1,3-(2-methyl)phenyl]dioxalamate (1) and resorcinol (2), namely 1·2cryst (C21H24N2O8) was prepared by mechanochemical complexation. IR spectroscopy and powder X-ray diffraction studies allowed to determine the complexation and the conformational switching of the ethyl oxalamate side arms. In the crystal structure of 1·2cryst, complexation occurs through O-H···O=C hydrogen-bonding interactions with the participation of phenolic O-H as donor and amide carbonyl group as acceptor. The steric hindrance of the CH3 group in the C-2 position of the aromatic ring leads to a meso-helical supramolecular architecture forming a C22 (16) chain motif. Crystal data: monoclinic, C2/c space group, a = 34.9054(13) Å, b = 8.0434(5) Å, c = 5.1577(8) Å, β = 97.521(3)°. Graphical Abstract: The cocrystal formed by diethyl N,N'-[1,3-(2-methyl)phenyl]dioxalamate and resorcinol, prepared by mechanochemical complexation.
KW - Cocrystal
KW - Helix
KW - Hydrogen bond
KW - Phenyldioxalamate
KW - Resorcinol
UR - http://www.scopus.com/inward/record.url?scp=84929572241&partnerID=8YFLogxK
U2 - 10.1007/s10870-015-0589-8
DO - 10.1007/s10870-015-0589-8
M3 - Artículo
SN - 1074-1542
VL - 45
SP - 244
EP - 250
JO - Journal of Chemical Crystallography
JF - Journal of Chemical Crystallography
IS - 5
ER -