(E)-2-[2-(4-Carb-oxy-phen-yl)ethen-yl]-8-hydroxy-quinolin-1-ium chloride ethanol monosolvate.

Mathias M Schulze,Edwin Weber,Wilhelm Seichter

doi:10.1107/s1600536813030274

Abstract

In the title compound, C18H14NO3 +·Cl−·CH3CH2OH, the dihedral angle formed by the mean planes of the quinolinium and benzene rings is 3.4 (1)°, while the carboxy substituent is tilted at an angle of 4.8 (1)° with respect to the benzene ring. There is a short N—H⋯O contact in the cation. In the crystal, due to the planar molecular geometry, two-dimensional aggregates are formed parallel to (221) via C—H⋯O, C—H⋯Cl, O—H⋯Cl and N—H⋯Cl hydrogen bonds. Interlayer association is accomplished by O—Hethanol⋯Cl and O—H⋯Oethanol hydrogen bonds and π–π stacking interactions [centroid–centroid distances vary from 3.6477 (12) to 3.8381 (11) Å]. A supramolecular three-dimensional architecture results from a stacked arrangement of layers comprising the ionic and hydrogen-bonded components.

Highlights

C18H14NO3+ClCH3CH2OH, the dihedral angle formed by the mean planes of the quinolinium and benzene rings is 3.4 (1), while the carboxy substituent is tilted at an angle of 4.8 (1) with respect to the benzene ring
For the preparative method used for the synthesis of the title compound, see: Yuan et al (2012)
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y, z+1; (iii) x+1, y+1, z; (iv) x−1, y−1, z

Summary

Data collection

Institut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany. R factor = 0.048; wR factor = 0.147; data-to-parameter ratio = 14.8. C18H14NO3+ClCH3CH2OH, the dihedral angle formed by the mean planes of the quinolinium and benzene rings is 3.4 (1) , while the carboxy substituent is tilted at an angle of 4.8 (1) with respect to the benzene ring. There is a short N—H O contact in the cation. Due to the planar molecular geometry, two-dimensional aggregates are formed parallel to (221) via C—H O, C—. H Cl, O—H Cl and N—H Cl hydrogen bonds. H Oethanol hydrogen bonds and – stacking interactions [centroid–centroid distances vary from 3.6477 (12) to. A supramolecular three-dimensional architecture results from a stacked arrangement of layers comprising the ionic and hydrogen-bonded components

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Findings

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