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. 2017 Jul 21;73(Pt 8):1232-1236.
doi: 10.1107/S2056989017010052. eCollection 2017 Jul 1.

Crystal structures of three 1-[4-(4-bromo-but-oxy)-phen-yl] chalcone derivatives: (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-phenyl-prop-2-en-1-one, (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-(4-meth-oxy-phen-yl)prop-2-en-1-one and (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one

Gunasekaran Maragatham  1 , Sivasamy Selvarani  2 , Perumal Rajakumar  2 , Srinivasakannan Lakshmi  1
Affiliations

Crystal structures of three 1-[4-(4-bromo-but-oxy)-phen-yl] chalcone derivatives: (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-phenyl-prop-2-en-1-one, (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-(4-meth-oxy-phen-yl)prop-2-en-1-one and (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one

Gunasekaran Maragatham et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The crystal structures of three chalcones with a bromo-substituted but-oxy side chain, viz. (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-phenyl-prop-2-en-1-one, C19H19BrO2, (I), (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-(4-meth-oxy-phen-yl)prop-2-en-1-one, C20H21BrO3, (II), and (E)-1-[4-(4-bromo-but-oxy)-phen-yl]-3-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one, C21H23BrO4, (III), are reported. In all mol-ecules, the conformation of the keto group with respect to the olefinic bond is s-cis. Mol-ecules of (I) and (II) are nearly planar, while mol-ecule (III) is not planar. In the crystal of compounds (I) and (II), mol-ecules are linked into chains parallel to the c axis by C-H⋯π inter-actions. In the crystal of compound (III), mol-ecules are linked by a pairs of C-H⋯O hydrogen bonds, forming inversion dimers. Weak C-Br⋯π inter-actions are also observed in (III).

Keywords: Claisen–Schmidt condensation reaction; C—Br⋯π contact; chalcones; crystal structures; hydrogen bonding; mol­ecular conformation.

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Figures

Figure 1
Figure 1
The mol­ecular structure of compound (I), with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small sphere of arbitrary radius.
Figure 2
Figure 2
The mol­ecular structure of compound (II), with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small sphere of arbitrary radius.
Figure 3
Figure 3
The mol­ecular structure of the compound (III), with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small sphere of arbitrary radius.
Figure 4
Figure 4
Crystal packing of the compound (I), viewed down the a axis.
Figure 5
Figure 5
Crystal packing of the compound (II), viewed down the a axis.
Figure 6
Figure 6
Crystal packing of the compound (III), viewed down the c axis. Hydrogen atoms not involved in hydrogen bonding (dashed lines) are omitted.
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