Crystal structure and Hirshfeld surface analysis of ethyl (E)-4-[(4-hy-droxy-3-meth-oxy-5-nitro-benzyl-idene)amino]-benzoate

Antony Samy Victoria; Palaniyappan Sivajeyanthi; Natarajan Elangovan; Kasthuri Balasubramani; Thathan Kolochi; Kanagasabapathy Thanikasalam

doi:10.1107/S2056989018009465

Crystal structure and Hirshfeld surface analysis of ethyl (E)-4-[(4-hy-droxy-3-meth-oxy-5-nitro-benzyl-idene)amino]-benzoate

Acta Crystallogr E Crystallogr Commun. 2018 Jul 10;74(Pt 8):1079-1082. doi: 10.1107/S2056989018009465. eCollection 2018 Aug 1.

Authors

Antony Samy Victoria¹, Palaniyappan Sivajeyanthi², Natarajan Elangovan¹, Kasthuri Balasubramani², Thathan Kolochi¹, Kanagasabapathy Thanikasalam³

Affiliations

¹ PG & Research Department of Chemistry, Government Arts College (Autonomous), Arignar Anna Government Arts College, Musiri 621 211, Tamil Nadu, India.
² Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu, India.
³ Department of Chemistry, Periyar EVR College (Autonomous), Thiruchirapalli 620 023, Tamil Nadu, India.

Abstract

The title Schiff base compound, C₁₇H₁₆N₂O₆, has an E configuration with respect to the C=N bond, with a dihedral angle between the two benzene rings of 31.90 (12)°. There is an intra-molecular O-H⋯O_nitro hydrogen bond present forming an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers enclosing an R₂²(4) ring motif. The dimers are linked about an inversion centre by pairs of C-H⋯O hydrogen bonds, which enclose R₂²(22) loops, forming chains propagating along the [10] direction. Hirshfeld surface analysis and fingerprint plots show enrichment ratios for the H⋯H, O⋯H and C⋯H contacts, indicating a high propensity of such inter-actions in the crystal. Both the nitro group and the CH₃-CH₂-O- group are positionally disordered.

Keywords: Hirshfeld surface analysis; Schiff base; crystal structure; hydrogen bonding.

Grants and funding

This work was funded by Department of Science and Technology, Ministry of Science and Technology, Science and Engineering Research Board grant SB/FT/CS-058/2013 to K. Balasubramani and P. Sivajeyanthi.