Intermolecularly associated carboxylic acid dimers in the supramolecular assembly of (r)-1,4-benzodioxane 2-carboxylic acid

Jasinski, Jerry P. and Butcher, Ray J. and Yathirajan, H. S. and Narayana, B. and Mallesha, L. and Mohana, K. N. (2009) Intermolecularly associated carboxylic acid dimers in the supramolecular assembly of (r)-1,4-benzodioxane 2-carboxylic acid. Journal of Chemical Crystallography, 39 (6). pp. 453-457. ISSN 1572-8854

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The title compound, C9H8O4, (I), crystallizes in the monoclinic space group P 21/c with unit cell parameters a = 7.3380(5) angstrom, b = 9.3790(7) angstrom, c = 12.3172(9) angstrom, beta = 90.687(7)degrees, Z = 4. The molecule consists of a benzene ring fused to a 1,4 dioxane ring in a half-chair conformation with a carboxylic acid group bonded at the dioxane 2-position. The carboxylic acid group forms a classic O-H center dot center dot center dot O hydrogen bonded dimer with an O center dot center dot center dot O distance of 2.6292(12) angstrom in a R-2(2) (8) graph-set motif which links the molecules into pairs around inversion centers in a supramolecular assembly in the unit cell. The dihedral angle between the mean planes of the R-2(2) (8) graph-set motif's of two adjacent dimers in the unit cell is 75.7(5)degrees. The mean plane of an R-2(2) (8) graph-set motif makes an angle of 88.4(5)degrees with the mean plane of the benzene ring in the same dimer and 13.1(2)degrees or 13.4(7)degrees with the mean plane of a benzene ring from an adjacent dimer. Additional weak Cg pi-ring intermolecular interactions significantly influence the bond distances, bond angles and torsion angles of the dioxane ring and attached carboxyl group. Comparison to a MOPAC AM1computational calculation provides support to these observations.

Item Type: Article
Uncontrolled Keywords: Benzene; Dioxane; Carboxylic acid; Dimer; R-2(2) (8) graph-set motif; MOPAC
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Users 19 not found.
Date Deposited: 26 Aug 2019 06:05
Last Modified: 26 Aug 2019 06:05

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