2-Anilino-4-(1,3-benzothiazol-2-yl)-5-(4-chlorobenzoyl)thiophene-3-carbonitrile

Hoong-Kun Fun,Tze Shyang Chia,Hatem A Abdel-Aziz

doi:10.1107/s1600536812032588

Hoong-Kun Fun, Tze Shyang Chia + Show 1 more

Open Access

https://doi.org/10.1107/s1600536812032588

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Abstract

In the title compound, C25H14ClN3OS2, the central thiophene ring [maximum deviation = 0.011 (1) Å] makes dihedral angles of 55.72 (5), 13.36 (5) and 46.77 (4)° with the adjacent chloro-substituted benzene ring, the benzene ring and the 1,3-benzothiazole ring system [maximum deviation = 0.012 (1) Å], respectively. An intramolecular C—H⋯S(thienyl) hydrogen bond generates an S(6) ring motif in the molecule. In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers and the dimers are further connected by C—H⋯O hydrogen bonds into tapes running along [100]. Aromatic π–π stacking interactions are also observed [centroid-to-centroid distances = 3.6116 (6) and 3.7081 (6) Å].

Highlights

In the title compound, C25H14ClN3OS2, the central thiophene ring [maximum deviation = 0.011 (1) A ] makes dihedral angles of 55.72 (5), 13.36 (5) and 46.77 (4) with the adjacent chlorosubstituted benzene ring, the benzene ring and the 1,3benzothiazole ring system [maximum deviation = 0.012 (1) A ], respectively
Molecules are linked by pairs of N—HÁ Á ÁN hydrogen bonds into inversion dimers and the dimers are further connected by C—HÁ Á ÁO hydrogen bonds into tapes running along [100]
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z

Summary

Structure Reports Online

C25H14ClN3OS2, the central thiophene ring [maximum deviation = 0.011 (1) A ] makes dihedral angles of 55.72 (5), 13.36 (5) and 46.77 (4) with the adjacent chlorosubstituted benzene ring, the benzene ring and the 1,3benzothiazole ring system [maximum deviation = 0.012 (1) A ], respectively. An intramolecular C—HÁ Á ÁS(thienyl) hydrogen bond generates an S(6) ring motif in the molecule. Molecules are linked by pairs of N—HÁ Á ÁN hydrogen bonds into inversion dimers and the dimers are further connected by C—HÁ Á ÁO hydrogen bonds into tapes running along [100]. Related literature For background to the chemistry and biological activity of thiophenes, see: Fun et al (2012); Abdel-Aziz et al (2012). For hydrogen-bond motifs, see: Bernstein et al (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986)

Bruker APEX DUO CCD diffractometer

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