Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with L-prolinol

Yuko Kawanami; Hidekazu Tanaka; Jun-ichi Mizoguchi; Nobuko Kanehisa; Gaku Fukuhara; Masaki Nishijima; Tadashi Mori; Yoshihisa Inoue

doi:10.1107/S0108270113028461

Absolute configuration determination of the anti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with L-prolinol

Acta Crystallogr C. 2013 Nov;69(Pt 11):1411-3. doi: 10.1107/S0108270113028461. Epub 2013 Oct 31.

Authors

Yuko Kawanami¹, Hidekazu Tanaka, Jun-ichi Mizoguchi, Nobuko Kanehisa, Gaku Fukuhara, Masaki Nishijima, Tadashi Mori, Yoshihisa Inoue

Affiliation

¹ Department of Applied Chemistry, Osaka University, Yamadaoka, Suita 565-0871, Japan.

PMID: 24192199
DOI: 10.1107/S0108270113028461

Abstract

The absolute configuration has been established of the enantiopure anti-head-to-head cyclodimer of anthracene-2-carboxylic acid (AC) cocrystallized with L-propinol and dichloromethane [systematic name: (S)-2-(hydroxymethyl)pyrrolidin-1-ium (5R,6S,11R,12S)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11-bis([1,2]benzeno)dibenzo[a,e][8]annulene-2-carboxylate dichloromethane monosolvate], C5H12NO(+)·C30H19O4(-)·CH2Cl2. In the crystal structure, the AC dimer interacts with L-prolinol through a nine-membered hydrogen-bonded ring [R2(2)(9)], while the dichloromethane molecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoretical versus experimental circular dichroism spectra.

Keywords: absolute configuration; anthracene-2-carboxylic acid; anti-head-to-head cyclodimer; circular dichroism spectra; crystal structure; l-prolinol.