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 ?-? 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?? contacts feature prominently in stabilizing the three-dimensional structure.

SUBMITTER: McAdam CJ 

PROVIDER: S-EPMC4719824 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature