title: Redetermination of the crystal structure of boron subphthalocyanine chloride (Cl-BsubPc) enabled by slow train sublimation.
abstract: The crystal structure of boron subphthalocyanine chloride [systematic name: chlorido(subphthalocyaninato)boron], C24H12BClN6, a material of widespread interest in organic electronic device applications, has been redetermined with a higher precision using large single crystals obtained via slow train sublimation. Details are given for the construction and operation of the train sublimation system, which has been designed to reproducibly yield single crystals suitable for diffraction experiments in a manner which approximates the vacuum deposition conditions commonly used to fabricate organic electronic devices. Diffraction experiments were conducted using two crystal samples and four temperatures (90, 123, 147 and 295 K), enabling a discussion of changes in the unit cell and intermolecular interactions with respect to temperature and in comparison to two previously published structures of Cl-BsubPc. The redetermined structure confirms the original structure published 41 years ago [Meller & Ossko (1972). Monatsh. Chem. 103, 150-155], with significantly improved precision for the geometric parameters. Analysis of the crystal structure revealed three intersecting ribbon motifs formed through a combination of π-π and halogen-π (specifically B-Cl...π) interactions. H atoms were refined independently in order to facilitate a thorough discussion of these intermolecular interactions using Hirshfeld surface analysis.
authors.affiliation: Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, Canada M5S 3E5.
authors.forename: Jessica D
authors.initials: JD
authors.lastname: Virdo
authors.affiliation: Department of Chemistry, University of Toronto, 80 St George St., Toronto, Ontario, Canada M5S 3H6.
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Lough
authors.affiliation: Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, Canada M5S 3E5.
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Bender
keywords: Hirshfeld surface analysis; boron; bowl-shaped molecule; chloride; crystal structure; diiminoisoindoline; fingerprint plot; organic electronic devices; redetermination; ribbon motif; subphthalocyanine; train sublimation; vacuum deposition