title: Crystal structures of 6-chloro-indan-1-one and 6-bromo-indan-1-one exhibit different inter-molecular packing inter-actions.
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).
authors.affiliation: Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.
authors.forename: Alessio
authors.initials: A
authors.lastname: Caruso
authors.affiliation: Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.
authors.forename: Benjamin
authors.initials: B
authors.lastname: Blair
authors.affiliation: Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Tanski
keywords: C—H⋯X inter­actions; crystal structure; haloindanones; π-stacking