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Title: Crystal structure of 8-hydroxyquinoline: a new monoclinic polymorph
In an attempt to grow 8-hydroxyquinoline–acetaminophen co-crystals from equimolar amounts of conformers in a chloroform–ethanol solvent mixture at room temperature, the title compound, C 9 H 7 NO, was obtained. The molecule is planar, with the hydroxy H atom forming an intramolecular O—H...N hydrogen bond. In the crystal, molecules form centrosymmetric dimers via two O—H...N hydrogen bonds. Thus, the hydroxy H atoms are involved in bifurcated O—H...N hydrogen bonds, leading to the formation of a central planar four-membered N 2 H 2 ring. The dimers are bound by intermolecular π–π stacking [the shortest C...C distance is 3.2997 (17) Å] and C—H...π interactions into a three-dimensional framework. The crystal grown represents a new monoclinic polymorph in the space group P 2 1 / n . The molecular structure of the present monoclinic polymorph is very similar to that of the orthorhombic polymorph (space group Fdd 2) studied previously [Roychowdhury et al. (1978). Acta Cryst. B 34 , 1047–1048; Banerjee & Saha (1986). Acta Cryst. C 42 , 1408–1411]. The structures of the two polymorphs are distinguished by the different geometries of the hydrogen-bonded dimers, which in the crystal of the orthorhombic polymorph possess twofold axis symmetry, with the central N 2 H 2 ring adopting a butterfly conformation.  more » « less
Award ID(s):
1301346
PAR ID:
10081630
Author(s) / Creator(s):
; ; ; ;
Date Published:
Journal Name:
Acta Crystallographica Section E Structure Reports Online
Volume:
70
Issue:
9
ISSN:
1600-5368
Page Range / eLocation ID:
o924 to o925
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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