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Two different modes of halogen bonding in two 4-nitroimidazole derivatives

Journal Article


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Abstract


  • In the crystal structures of the two imidazole derivatives 5-chloro-1,2-dimethyl-4-nitro-1H-imidazole, C5H6ClN3O2, (I), and 2-chloro-1-methyl-4-nitro-1H-imidazole, C4H4ClN3O2, (II), C—Cl...O halogen bonds are the principal specific interactions responsible for the crystal packing. Two different halogen-bond modes are observed: in (I), there is one very short and directional C—Cl...O contact [Cl...O = 2.899 (1) Å], while in (II), the C—Cl group approaches two different O atoms from two different molecules, and the contacts are longer [3.285 (2) and 3.498 (2) Å] and less directional. In (I), relatively short C—H...O hydrogen bonds provide the secondary interactions for building the crystal structure; in (II), the C—H...O contacts are longer but there is a relatively short π–π contact between molecules related by a centre of symmetry. The molecule of (I) is almost planar, the plane of the nitro group making a dihedral angle of 6.97 (7)° with the mean plane of the imidazole ring. The molecule of (II) has crystallographically imposed mirror symmetry and the nitro group lies in the mirror plane.

UOW Authors


Publication Date


  • 2007

Citation


  • Kubicki, M. & Wagner, P. (2007). Two different modes of halogen bonding in two 4-nitroimidazole derivatives. Acta Crystallographica Section C: Crystal Structure Communications, 63 (8), o454-o457.

Scopus Eid


  • 2-s2.0-34547778502

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2051&context=aiimpapers

Ro Metadata Url


  • http://ro.uow.edu.au/aiimpapers/1050

Start Page


  • o454

End Page


  • o457

Volume


  • 63

Issue


  • 8

Abstract


  • In the crystal structures of the two imidazole derivatives 5-chloro-1,2-dimethyl-4-nitro-1H-imidazole, C5H6ClN3O2, (I), and 2-chloro-1-methyl-4-nitro-1H-imidazole, C4H4ClN3O2, (II), C—Cl...O halogen bonds are the principal specific interactions responsible for the crystal packing. Two different halogen-bond modes are observed: in (I), there is one very short and directional C—Cl...O contact [Cl...O = 2.899 (1) Å], while in (II), the C—Cl group approaches two different O atoms from two different molecules, and the contacts are longer [3.285 (2) and 3.498 (2) Å] and less directional. In (I), relatively short C—H...O hydrogen bonds provide the secondary interactions for building the crystal structure; in (II), the C—H...O contacts are longer but there is a relatively short π–π contact between molecules related by a centre of symmetry. The molecule of (I) is almost planar, the plane of the nitro group making a dihedral angle of 6.97 (7)° with the mean plane of the imidazole ring. The molecule of (II) has crystallographically imposed mirror symmetry and the nitro group lies in the mirror plane.

UOW Authors


Publication Date


  • 2007

Citation


  • Kubicki, M. & Wagner, P. (2007). Two different modes of halogen bonding in two 4-nitroimidazole derivatives. Acta Crystallographica Section C: Crystal Structure Communications, 63 (8), o454-o457.

Scopus Eid


  • 2-s2.0-34547778502

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2051&context=aiimpapers

Ro Metadata Url


  • http://ro.uow.edu.au/aiimpapers/1050

Start Page


  • o454

End Page


  • o457

Volume


  • 63

Issue


  • 8