Crystal structure, Hirshfeld surface and computational study of 1-(9,10-dioxo-9,10-di-hydroanthracen-1-yl)-3-propano-ylthio-urea

Kenechukwu J Ifeanyieze; Bikimi B Ayiya; Obinna C Okpareke; Tatiana V Groutso; Jonnie N Asegbeloyin

doi:10.1107/S2056989022003127

Crystal structure, Hirshfeld surface and computational study of 1-(9,10-dioxo-9,10-di-hydroanthracen-1-yl)-3-propano-ylthio-urea

Acta Crystallogr E Crystallogr Commun. 2022 Mar 29;78(Pt 4):439-444. doi: 10.1107/S2056989022003127. eCollection 2022 Apr 1.

Authors

Kenechukwu J Ifeanyieze¹, Bikimi B Ayiya², Obinna C Okpareke¹, Tatiana V Groutso³, Jonnie N Asegbeloyin¹

Affiliations

¹ Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, Nigeria.
² Universal College of Learning, Private Bag 11022, Palmerston North, New Zealand.
³ School of Chemical Sciences, the University of Auckland, New Zealand.

Abstract

The title compound, C₁₈H₁₄N₂O₃S, crystallizes in the ortho-rhom-bic crystal system and Pbca space group. The thio-urea chromophore is planar to an r.m.s deviation of 0.032 Å with the thiol-ate sulfur atom being the most deviated. Bifurcated N-H⋯O intra-molecular hydrogen bonds result in an S(6) supra-molecular synthon. In the crystal, mol-ecules are linked by N-H⋯O inter-molecular hydrogen-bonding inter-actions and stabilized by C-H⋯π and π-π inter-actions. Hirshfeld surface analysis and fingerprint plot indicate the H⋯H inter-molecular contacts as the highest contributor to the overall surface contacts (38%) and this is supported by the high dispersive and electrostatic inter-action energies.

Keywords: Hirshfeld surface; anthraquinone; computational study; crystal structure; thiourea.