IUPAC name: 2-(2H-1-benzopyran-2-imin-3-yl)-4-(2H-1-benzopyran-2-one-3-yl)thiazole.
Article first published online: 14 SEP 2004
Copyright © 1993 John Wiley & Sons Ltd.
Advanced Materials for Optics and Electronics
Volume 2, Issue 4, pages 191–195, July/August 1993
How to Cite
Baumer, V. N., Ponomaryov, O. A., Novikov, A. I., Lakin, E. E. and Kuznetsov, V. P. (1993), Structure of 2-(iminocoumar-3-yl)-4-(coumar-3-yl)-thiazole, C2lHl4N2O3S. Adv. Mater. Opt. Electron., 2: 191–195. doi: 10.1002/amo.860020406
Supplementary data comprising full bond lengths and angles, atomic co-ordinates and anisotropic thermal parameters can be obtained from the Cambridge Crystallographic Data Centre; see Notes for Contributors for ordering information.
- Issue published online: 14 SEP 2004
- Article first published online: 14 SEP 2004
- Manuscript Accepted: 14 FEB 1993
- Manuscript Received: 1 DEC 1992
- Laser dyes;
- Bifluorophoric compounds;
- Thiazolyl derivatives;
- Crystal structure;
- Molecular conformation
We have determined the structure of 2-(iminocouma-3-yl)-4-(coumar-3-yl)-thiazole, C21H14N2O3S, Mr=372.4, λ = 0.71073 Å, monoclinic, space group P21/n, a = 9.472(2) Å, b = 11.284(2) Å, c = 15.821(3) Å, β = 86.50(2)°, V = 1687.9(6) Å3, Z = 4, Dx = 1.465 Mg m−3, μ(Mo Kα) = 0.207 mm−1, F(000) = 768, S = 1.91, R = 3.82%, wR = 3.26% for 1251 observed reflections (F > 6σF). In the observed conformation of the molecule the imino group forms an intramolecular H…S bond of length 2.26 Å and the carbonyl oxygen makes a short contact with the hydrogen atom of the thiazolyl cycle. The molecule is planar. In the crystal structure a particular disorder of about 20% of molecules is observed with respect to the pseudo-mirror plane which is perpendicular to the molecular plane and passes through the thiazolyl N atom and the middle of the SCH bond. The disagreement found between the observed conformation and that predicted by molecular mechanics calculations is explained by the tendency of the molecule to have the lowest value of dipole moment due to minimisation of the electrostatic contribution to the energy.