Crystal structure and Hirshfeld surface analysis of 3-(3-hy-droxy-phen-yl)-1-(1 H-pyrrol-2-yl)prop-2-en-1-one hemihydrate

Ahmad Zaidi Ismail; Mohanapriya Gunasekharan; Thiruventhan Karunakaran; Siti Munirah Mohd Faudzi

doi:10.1107/S2056989023001925

Crystal structure and Hirshfeld surface analysis of 3-(3-hy-droxy-phen-yl)-1-(1 H-pyrrol-2-yl)prop-2-en-1-one hemihydrate

Acta Crystallogr E Crystallogr Commun. 2023 Mar 10;79(Pt 4):287-291. doi: 10.1107/S2056989023001925. eCollection 2023 Mar 1.

Authors

Ahmad Zaidi Ismail^{1

2}, Mohanapriya Gunasekharan², Thiruventhan Karunakaran³, Siti Munirah Mohd Faudzi^{2

4}

Affiliations

¹ School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand.
² Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang, 43400, Selangor, Malaysia.
³ Centre for Drug Research, Universiti Sains Malaysia, 11800 USM, Pulau Pinang, Malaysia.
⁴ Natural Medicines and Product Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, 43400, Selangor, Malaysia.

Abstract

High-quality single crystals of the title compound, 2C₁₃H₁₁NO₂·H₂O, were grown and a structural analysis was performed. The asymmetric unit comprises one mol-ecule of 3-(3-hy-droxy-phen-yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (3HPPP), which was recently discovered to be a promising anti-MRSA candidate, and a half-mol-ecule of water. The compound crystallizes in the monoclinic space group P2/c. The crystal structure features inter-molecular pyrrole-N-H⋯O (water), carbon-yl/keto-C-O⋯H-O-phenol and phenol-C-O⋯H (water) hydrogen bonds, which help to consolidate the crystal packing. A Hirshfeld surface analysis for the components in the asymmetric unit showed that H⋯H (40.9%) and H⋯C/C⋯H (32.4%) contacts make the largest contributions to the inter-molecular inter-actions of 3HPPP. Considering the presence of water, in its vicinity H⋯O/O⋯H and H⋯C/C⋯H are the most significant contacts, contributing 48.7 and 29.8%, respectively.

Keywords: SCXRD; chalcone; crystal structure; pyrrole; pyrrole-derived chalcone.

Grants and funding

The authors acknowledge the Ministry of Higher Education, Malaysia under the Fundamental Research Grant Scheme (FRGS) (grant No. FRGS/1/2018/STG01/UPM/02/8; vote number of 55401477) and Universiti Putra Malaysia under the Putra grant – Putra Graduates Initiative (IPS)(GP-IPS/2018/9618500) for their financial support.