Crystal structure of 2-chloro-3-(di­meth­­oxy­meth­yl)-6-meth­­oxy­quinoline

Chandrika, N. and Suresha Kumara, T. H. and Jasinski, Jerry P. and Millikan, Sean P. and Yathirajan, H. S. and Glidewell, Christopher (2015) Crystal structure of 2-chloro-3-(di­meth­­oxy­meth­yl)-6-meth­­oxy­quinoline. Acta Crystallographica Section E, 71 (5). o364-o365. ISSN 2056-9890

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The title compound, C13H14ClNO3, crystallizes with Z′ = 2 in the space group Pca21, but a search for possible additional crystallographic symmetry found none. However, the crystal structure exhibits pseudosymmetry as the two independent mol­ecules are related by an approximate but non-crystallographic inversion located close to (0.38, 0.26, 1/2) in the selected asymmetric unit, and the structure exhibits partial inversion twinning. The approximate inversion relationship between the two mol­ecules in the selected asymmetric unit is clearly shown by comparison of the relevant torsion angle in the two mol­ecules; the corresponding torsion angles have similar, although not identical magnitudes but with opposite signs. The mean planes of the quinoline rings in the two independent mol­ecules are almost parallel, with a dihedral angle of only 0.16 (3)° between them, and the mutual orientation of these rings permits significant π–π stacking inter­actions between them [centroid–centroid distances = 3.7579 (15) and 3.7923 (15) Å]. In addition, the bimolecular aggregates which are related by translation along [010] are linked by a further π–π stacking inter­action [centroid–centroid distance = 3.7898 (15) Å], so forming a π-stacked chain running parallel to [010]. However, there are no C—H⋯N hydrogen bonds in the structure nor, despite the number of independent aromatic rings, are there any C—H⋯π hydrogen bonds; hence there are no direction-specific inter­actions between adjacent π-stacked chains.

Item Type: Article
Uncontrolled Keywords: crystal structure, quinolone, pseudosymmetry, twinning, pi-pi stacking interactions
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: MUL SWAPNA user
Date Deposited: 08 Nov 2019 06:02
Last Modified: 08 Nov 2019 06:02

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