Abstract
The crystal structure of C14H12ClNO2 was determined by X-ray analysis. It crystallizes in the triclinic space group Pc with a = 12.5346(10) Å, b = 4.5101(3) Å, c = 12.0534(11) Å, α = 90.00º, β = 113.669(6)º, γ = 90.00º, Z = 2, Dx = 1.393 mg/m3, μ (MoKα) = 0.298 mm−1. The title compound is photochromic and molecule is non-planar. It adopts a phenol–imine tautomeric form with a strong intramolecular O–H···N hydrogen bond and a strong intermolecular C–H···O hydrogen bond. Minimum energy conformations AM1 were calculated as a function of the three torsion angles θ1(C10–C9–N1–C8), θ2(C9–N1–C8–C1) and θ3(N1–C8–C1–C6), varied every 10°. As in the X-ray experiment results, molecule has an angle that makes it non-planar between two aromatic rings in AM1 optimized geometry.
Graphical Abstract
Molecular and crystal structure of [(E)-2-[(3-chlorophenylimino)methy])-4-methoxyphenol], C14H12ClNO2, have been determined by single crystal X-ray diffraction study, and conformational analysis of the title molecule with respect to the selected torsion angle has been achieved by AM1 semi-empirical calculations.
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Acknowledgments
The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the STOE IPDS 2 diffractometer (purchased under Grant F.279 of the University Research Fund).
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Özek, A., Albayrak, Ç., Odabaşoğlu, M. et al. Crystallographic and Conformational Analysis of [(E)-2-[(3-Chlorophenylimino)methy])-4-methoxyphenol]. J Chem Crystallogr 39, 353–357 (2009). https://doi.org/10.1007/s10870-008-9483-y
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DOI: https://doi.org/10.1007/s10870-008-9483-y