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Z. Naturforsch. 2012,
67b, 1273 – 1281
doi:10.5560/ZNB.2012-0249
X-Ray Structure Determinations of Bromo- and/or Bromomethyl-substituted Benzenes: C–H···Br, C–Br···Br, and C–Br··· π Interactions
1 Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
2 Department of Chemistry, University of Silesia, 9, Szkolna Street, 40-006 Katowice, Poland
3 Institut für Anorganische Chemie, Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany. Current address: Novartis Pharma AG, CH-4056 Basel, Switzerland
Reprint requests to Prof. Dr. P. G. Jones. Fax: +49-531-391-5387. E-mail:
p.jones@tu-bs.de.
Received September 18, 2012 / published online November 30, 2012
Belatedly dedicated to Professor Joachim Heinicke on the occasion of his 65th birthday
The structures of seven benzene derivatives [1,2,3-tri(bromomethyl)benzene, (1); 3,5-di(bromomethyl)bromobenzene, (2); 2,5-di(bromomethyl)bromobenzene, (3); 4-(bromomethyl)-2,5-dibromotoluene, (4); 4-(bromomethyl)bromobenzene, (5); 2,3-di(bromomethyl)bromobenzene, (6) and (bromomethyl)-p-dibromobenzene, (7)] with bromo and bromomethyl (and in one case methyl) substituents are presented and analysed in terms of Br···Br interactions up to 4.0 Å, supported by hydrogen bonds H···Br. Some interactions of the type Br··· π and π ··· π are encountered and play a subordinate role in the packing. Despite the close chemical similarity of the compounds, some of which are isomers with permuted
substituent positions, the packing motifs are highly variable. Compounds 2–5 are based on layer structures with Brn (n = 3, 4) and/or mixed Br/C rings. Compounds 1, 6 and 7 display three-dimensional packings of differing complexity, but with interpretable substructures; 1 can be analysed in terms of ribbons of linked Br3 and Br4 rings; 6 displays chains of linked Br3 triangles; 7 consists of ribbons of linked Br4 quadrilaterals.
Key words: Halogen Bonds, “Weak” Hydrogen Bonds, Secondary Interactions