(2E)-3-(5-Bromo-2-thienyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

Abstract

Key indicators: single-crystal X-ray study; T = 173 K; mean (C-C) = 0.003 Å; R factor = 0.031; wR factor = 0.066; data-to-parameter ratio = 15.5.Geometric parameters of the title compound, C 13 H 9 BrO 2 S, a chalcone derivative, are in the usual ranges. The C C double bond is trans configured. The molecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.069 Å ). The crystal packing is stabilized by an O-HÁ Á ÁO hydrogen bond. Related literature ExperimentalCrystal data

(E)-1-(Benzo[d][1,3]dioxol-5-yl)-3-([2,2′-bithiophen]-5-yl)prop-2-en-1-one: crystal structure, UV–Vis analysis and theoretical studies of a new π-conjugated chalcone

“…In terms of intermolecular interactions, (E)-1-(2-aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one (Chantrapromma et al, 2013) exhibits a strong intermolecular C-HÁ Á ÁO interaction by which two adjacent molecules are linked in an antiparallel face-to-face manner into chains along the c-axis direction. Meanwhile, a weak intermolecular O-HÁ Á ÁO interaction is observed in (2E)-3-(5-bromo-2-thienyl)-1-(4hydroxyphenyl)prop-2-en-1-one (Narayana et al, 2007). Similar to the situation in (I), weak intermolecular C-HÁ Á Á interactions link the molecules of 1-(4-bromophenyl)-3-(2thienyl)prop-2-en-1-one (Patil et al, 2006) into chains along the b-axis direction.…”

“…A search of the Cambridge Structural Database (Version 5.39, last update November 2017; Groom et al, 2016) revealed four thiophene-substituted compounds with a different ketone on the chalcone: (E)-1-(2-aminophenyl)-3-(thiophen-2-yl)prop-2en-1-one (Chantrapromma et al, 2013), (2E)-3-(5-bromo-2thienyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (Narayana et al, 2007), 1-(4-bromophenyl)-3-(2-thienyl)prop-2-en-1-one (Patil et al, 2006) and (2E)-1-(4-bromophenyl)-3-(thiophen-2yl)prop-2-en-1-one (Arshad et al, 2017). Other related compounds that have a similar benzo[d]dioxol substituent on the chalcone are (2E)-1-(1,3-benzodioxol-5-yl)-3-(4-chlorophenyl)prop-2-en-1-one (Sreevidya et al, 2010) and ( The (a) experimental and (b) calculated UV-Vis absorption spectra.…”