Reinvestigation of the crystal structure of N-(4-chloro-benzyl-idene)-2-hy-droxy-aniline: a three-dimensional structure containing O-H⋯N, O-H⋯O and C-H⋯π(arene) hydrogen bonds.

Marisiddaiah Girisha,Christopher Glidewell,Ravindranath S Rathore,Hemmige S Yathirajan

doi:10.1107/s205698901800244x

Marisiddaiah Girisha, Christopher Glidewell + Show 2 more

Open Access

https://doi.org/10.1107/s205698901800244x

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Abstract

The mol-ecule of the title compound, C13H10ClNO, (I), which contains an intra-molecular O-H⋯N hydrogen bond, is almost planar: the dihedral angle between the two aryl rings is only 3.31 (9)°. The mol-ecules of (I) are linked into sheets by two C-H⋯π(arene) hydrogen bonds and the sheets are linked into a three-dimensional structure by O-H⋯O hydrogen bonds. Comparisons are made with the structures of a number of related compounds.

Highlights

The molecule of the title compound, C13H10ClNO, (I), which contains an intramolecular O—HÁ Á ÁN hydrogen bond, is almost planar: the dihedral angle between the two aryl rings is only 3.31 (9)
The molecules of (I) are linked into sheets by two C—HÁ Á Á(arene) hydrogen bonds and the sheets are linked into a three-dimensional structure by O—HÁ Á ÁO hydrogen bonds
Scrutiny of the reported structure reveals a number of unexpected features: the refinement was conducted in a non-standard monoclinic cell having < 90; the C—C distances in the aryl rings range between 1.336 and 1.427 A ; no H atoms bonded to C atoms were included; and the C—O—H angle was reported as 88, which seems very small, while the associated intramolecular HÁ Á ÁN distance was only 1.66 A, which is very short, even for a strong O—HÁ Á ÁN hydrogen bond

Summary

Chemical context

Schiff bases exhibit a very wide range of biological activities (da Silva et al, 2011) and are of interest because of the photochromic and thermochromic properties (Hadjoudis & Mavridis, 2004; Minkin et al, 2011). Scrutiny of the reported structure reveals a number of unexpected features: the refinement was conducted in a non-standard monoclinic cell having < 90; the C—C distances in the aryl rings range between 1.336 and 1.427 A ; no H atoms bonded to C atoms were included; and the C—O—H angle was reported as 88, which seems very small, while the associated intramolecular HÁ Á ÁN distance was only 1.66 A , which is very short, even for a strong O—HÁ Á ÁN hydrogen bond. The structures of several positional isomers of (I) have been reported recently (Kazak et al, 2004; Sundararaman et al, 2007; Saranya et al, 2015) and in view of these reports and of the widespread applications of Schiff bases, we have collected a new data set for compound (I), whose structure we report here (Fig. 1)

Structural commentary

Supramolecular features

Database survey