(S)-N-[1-(5-Benzyl-sulfan-yl-1,3,4-oxa-diazol-2-yl)-2-phenyl-eth-yl]-4-methyl-benzene-sulfonamide

Abstract

The title compound, C(24)H(23)N(3)O(3)S(2), crystallizes with two independent mol-ecules in the asymmetric unit. They differ essentially in the orientation of the tolyl rings, between which there is π-π stacking (centroid-centroid distance = 3.01 Å). The absolute configuration was confirmed by the determination of the Flack parameter [x = 0.008 (9)]. In the crystal, mol-ecules are connected by two classical N-H⋯N hydrogen bonds and two weak but very short C-H⋯O(sulfon-yl) inter-actions, forming layers lying parallel to the bc plane.

Fig. 1.

The molecular structure of the title compound, showing the numbering scheme for the two independent molecules (1 left; 2 right). Displacement ellipsoids are drawn at the 50% probability levels.

Fig. 2.

A least-squares fit of the two independent molecules (molecule 1 dotted lines). All non-H atoms were fitted except the ring atoms (C15–C20) on the left-hand side of the figure.

Fig. 3.

Crystal packing of the title compound, viewed perpendicular to the bc plane in the region x≈ 7/8. Thick dashed lines represent classical and thin dashed lines "weak" hydrogen bonds. Hydrogen atoms not involved in these interactions have been omitted for clarity. The three vertical rows of molecules are composed of molecules 2, 1, 2, respectively.