Abstract
The two title compounds are analogs of 1-indanone that are substituted at the 6-position with chlorine and bromine. Although very similar in mol-ecular structure, the crystal structures are not isomorphous and reveal that 6-chloro-indan-1-one, C9H7ClO (I), and 6-bromo-indan-1-one, C9H7BrO (II), exhibit unique inter-molecular packing motifs. The mol-ecules of the chloro analog (I) pack with a herringbone packing motif of C-H⋯O inter-actions, whereas the bromo derivative (II) packs with offset face-to-face π-stacking, C-H⋯O, C-H⋯Br and Br⋯O inter-actions. Compound (II) was refined as a two-component non-merohedral twin, BASF 0.0762 (5).
Highlights
Halogenated derivatives of the common bicyclic organic framework 1-indanone have been shown to be useful in a variety of synthetic and biologically related applications (Ruiz et al, 2004)
The compounds 6-chloroindan-1-one (I) and 6-bromoindan-1-one (II) may be synthesized by the microwave or ultrasound-aided ring closure of 4-chloro- or 4-bromobenzenepropanoic acid, respectively, catalyzed by triflic acid in dichloromethane (Oliverio et al, 2014). 6-Haloindan-1-ones have featured in the synthesis of biologically or pharmacologically active compounds
6-bromoindan-1-one (II) (Fig. 2) are similar to those reported for the analogous structure 6-fluoroindan-1-one
Summary
Halogenated derivatives of the common bicyclic organic framework 1-indanone have been shown to be useful in a variety of synthetic and biologically related applications (Ruiz et al, 2004). The title compounds represent two analogs of 6-haloindan-1-one that are notably not isomorphous. They are not isomorphous with the fluorine derivative 6-fluoroindan-1-one, which is one of the four that has previously been reported (Slaw & Tanski, 2014). 6-chloroindan-1one (I), the molecules pack together via a series of C—H O interactions. The bromo derivative 6-bromoindan-1-one (II) packs with offset face-to-face -stacking (Hunter & Saunders, 1990; Lueckheide et al, 2013) and several different intermolecular contacts including C—H O, C—H Br weak hydrogen bonds and Br O interactions. C-7 substituted 3,4-dihydroisoquinolin-1(2H)-one analogues that selectively inhibit unique poly-ADP-ribose polymerases (Morgan et al, 2015)
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