Crystal structure of 2-((1E)-{2-[bis(2-methylbenzylsulfanyl)methylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol

• Main Authors: Enis Nadia Md Yusof, Thahira Begum S. A. Ravoof, Mohamed Ibrahim Mohamed Tahir, Edward R. T. Tiekink
• Format: Article
• Language: English
• Published: International Union of Crystallography 2015-04-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; S-substituted dithiocarbazates; hydrogen bonding; C—H...π interactions; π–π interactions
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989015004946

In the title compound, C25H26N2O2S2, the central CN2S2 atoms are almost coplanar (r.m.s. deviation = 0.0058 Å). One phenyl ring clearly lies to one side of the central plane, while the other is oriented in the plane but splayed. Despite the different relative orientations, the phenyl rings form similar dihedral angles of 64.90 (3) and 70.06 (3)° with the central plane, and 63.28 (4)° with each other. The benzene ring is twisted with respect to the central plane, forming a dihedral angle of 13.17 (7)°. The S2C=N, N—N and N—N=C bond lengths of 1.2919 (19), 1.4037 (17) and 1.2892 (19) Å, respectively, suggest limited conjugation over these atoms; the configuration about the N—N=C bond is E. An intramolecular O—H...N hydrogen bond is noted. In the crystal, phenyl–methoxy C—H...O and phenyl–phenyl C—H...π interactions lead to supramolecular double chains parallel to the b axis. These are connected into a layer via methyl–phenyl C—H...π interactions, and layers stack along the a axis, being connected by weak π–π interactions between phenyl rings [inter-centroid distance = 3.9915 (9) Å] so that a three-dimensional architecture ensues.