Acta Cryst. (2002). E58, o1065-o1067  [ doi:10.1107/S1600536802015763 ]

9-(Thio-2'-methyl-4'-nitrophenyl) acridine

A. Mrozek, J. Karolak-Wojciechowska, P. Amiel and J. Barbe

Abstract: All interatomic distances in the title compound, C₂₀H₁₄N₂O₂S, (I), are normal. The molecule consists of two cyclic moieties, an acridine and a substituted phenyl ring. The two rings are joined via a sulfur bridge [S-C = 1.782  (3) and 1.764  (4)  Å]. The substituted phenyl ring in (I) is nearly perpendicular to the acridine moiety, with a dihedral angle of 75.01  (7)°. The acridine skeleton is slightly bent, with dihedral angles between the two terminal carbocyclic rings and the central heterocycle of 1.2  (1) and 0.5  (1)°. The molecules of the title compound stack head-to-tail along the b axis, with a distance between molecules of about 4.381  Å. In order to investigate quantitatively the aromaticity in acridines, we calculated the HOMA index [Krygowski (1993). J. Chem. Inf. Comput. Sci. 33, 70.] for each of the acridine rings; values were 0.568 and 0.524 for the carbocyclic rings and 0.816 for the heterocycle.

Online 13 September 2002

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