Redetermination of 4-nitro-stilbene

Abstract

In the title compound, C(14)H(11)NO(2), the benzene rings are inclined to each other with a dihedral angle between their mean planes of 8.42 (6)°. The nitro group is almost coplanar with the attached benzene ring but is rotated about the C-N bond by 5.84 (12)°. This redetermination results in a crystal structure with significantly higher precision than the original determination [Hertel & Romer (1931 ▶). Z. Kristallogr.76, 467-469], and the intermolecular interactions have been established. In the crystal structure, mol-ecules are linked by C-H⋯O hydrogen bonds to generate C(5), C(13) and edge-fused R(3) (3)(28) rings.

Fig. 1.

An ORTEP-3 (Farrugia, 1997) plot of the (I) compound, with the atomic labelling scheme. The shapes of the ellipsoids correspond to 50% probability contours of atomic displacement and, for the sake of clarity, H atoms are shown as spheres of arbitrary radius.

Fig. 2.

(Part of the crystal structure of (I) showing the formation of C(5) chains which are running parallel to the [100] direction. [Symmetry codes: (i) 1/2 + x, 1/2 - y, 2 - z; (ii) 1 + x, y, z; (iii) -1/2 + x, 1/2 - y, 2 - z; (iv) -1 + x, y, z].

Fig. 3.

Part of the crystal structure of (I) showing the formation of C(13) chains along [001]. [Symmetry codes: (i) x, 1/2 - y, 1/2 + z; (ii) x, 1/2 - y, -1/2 + z;

Fig. 4.

Part of the crystal structure of (I) showing the formation of edge-fused R33(28) rings along [001]. [Symmetry codes: (i) 3/2 - x, -y, 1/2 + z; (ii) x, 1/2 - y, 1/2 + z; (iii) 3/2 - x, 1/2 + y, z; (iv) 3/2 - x, -y, -1/2 + z]; (v) x, 1/2 - y, -1/2 + z; (vi) x, y, -1 + z; (vii) 3/2 - x, y, -1 + z.