title: Crystal structures of two bis-(iodo-meth-yl)benzene derivatives: similarities and differences in the crystal packing.
abstract: The isomeric derivatives 1,2-bis-(iodo-meth-yl)benzene, (I), and 1,3-bis-(iodo-meth-yl)benzene (II), both C8H8I2, were prepared by metathesis from their di-bromo analogues. The ortho-derivative, (I), lies about a crystallographic twofold axis that bis-ects the C-C bond between the two iodo-methyl substituents. The packing in (I) relies solely on C-H⋯I hydrogen bonds supported by weak parallel slipped π-π stacking inter-actions [inter-centroid distance = 4.0569 (11) Å, inter-planar distance = 3.3789 (8) Å and slippage = 2.245 Å]. While C-H⋯I hydrogen bonds are also found in the packing of (II), type II, I⋯I halogen bonds [I⋯I = 3.8662 (2) Å] and C-H⋯π contacts feature prominently in stabilizing the three-dimensional structure.
authors: Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.
authors: C John
authors: CJ
authors: McAdam
authors: Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.
authors: Lyall R
authors: LR
authors: Hanton
authors: Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.
authors: Stephen C
authors: SC
authors: Moratti
authors: Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.
authors: Jim
authors: J
authors: Simpson
keywords: C—H⋯I hydrogen bonds; C—H⋯π(ring) contacts; I⋯I halogen bonds; bis­(iodo­meth­yl)benzene derivatives; crystal structure; π–π contacts