Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 9 (September 2013)

organic compounds

Acta Cryst. (2013). C69, 1073-1076    [ doi:10.1107/S0108270113022142 ]

3,4-Dimethyl-N-[1-(1H-pyrrol-2-yl)ethyl­idene]aniline and the 1-(1-thio­phen-2-yl) analogue

B.-Y. Su, J.-X. Wang, X. Liu and Q.-D. Li

Abstract: The title compounds, 3,4-dimethyl-N-[1-(1H-pyrrol-2-yl)ethyl­idene]aniline, C14H16N2, (I), and its analogue 3,4-dimethyl-N-[1-(1-thio­phen-2-yl)ethyl­idene]aniline, C14H15NS, (II), both have basic heterocyclic imino structures showing a planar backbone with similar features, but differing in the hetero­atoms of the five-membered heterocyclic rings, i.e. N in (I) and S in (II). The dihedral angles formed by the five-membered and benzene rings are 81.78 (8) and 75.89 (7)° for (I) and (II), respectively. In (I), centrosymmetric imino­pyrrole dimers are assembled by means of two inverted N-H...N hydrogen bonds and two inverted C-H...[pi] inter­actions. In (II), however, mol­ecules are linked by nonclassical C-H...N hydrogen bonds in which the mol­ecules act as both hydrogen-bond donors and acceptors, resulting in one-dimensional supra­molecular chains.

Formula: C14H16N2 and C14H15NS

Keywords: crystal structure; hydrogen bonding; heterocyclic imino structures; one-dimensional supra­molecular chains.

hkldisplay filedownload file

Structure factor file (CIF format) (127.9 kbytes)
[ doi:10.1107/S0108270113022142/cu3033Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (112.8 kbytes)
[ doi:10.1107/S0108270113022142/cu3033IIsup3.hkl ]
Contains datablock II


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