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

被引:20
作者
Kubicki, Maciej [1 ]
Wagner, Pawel
机构
[1] Adam Mickiewicz Univ, Dept Chem, Grunwaldzka 6, PL-60780 Poznan, Poland
[2] Massey Univ, Nanomat Res Ctr, Palmerston North, New Zealand
[3] Massey Univ, MacDiarmid Inst Adv Mat & Nanotechnol, Palmerston North, New Zealand
来源
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2007年 / 63卷 / 08期
关键词
D O I
10.1107/S0108270107029721
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 center dot center dot center dot 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 center dot center dot center dot O contact [ Cl center dot center dot center dot O = 2.899 ( 1) A], 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) A] and less directional. In ( I), relatively short C - H center dot center dot center dot O hydrogen bonds provide the secondary interactions for building the crystal structure; in ( II), the C - H center dot center dot center dot O contacts are longer but there is a relatively short pi-pi 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) degrees 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.
引用
收藏
页码:O454 / O457
页数:4
相关论文
共 35 条
[1]   Halogen•••O(nitro) supramolecular synthon in crystal engineering:: A combined crystallographic database and ab initio molecular orbital study [J].
Allen, FH ;
Lommerse, JPM ;
Hoy, VJ ;
Howard, JAK ;
Desiraju, GR .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1997, 53 :1006-1016
[2]   The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].
Allen, FH .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388
[3]   STRUCTURAL CHEMISTRY OF DONOR-ACCEPTOR INTERACTIONS [J].
BENT, HA .
CHEMICAL REVIEWS, 1968, 68 (05) :587-&
[4]   PATTERNS IN HYDROGEN BONDING - FUNCTIONALITY AND GRAPH SET ANALYSIS IN CRYSTALS [J].
BERNSTEIN, J ;
DAVIS, RE ;
SHIMONI, L ;
CHANG, NL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (15) :1555-1573
[5]   The experimental electron density distribution in the complex of (E)-1,2-bis(4-pyridyl) ethylene with 1,4-diiodotetrafluorobenzene at 90 K [J].
Bianchi, R ;
Forni, A ;
Pilati, T .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (07) :1631-1638
[6]   Experimental electron density study of the supramolecular aggregation between 4,4′-dipyridyl-N,N′-dioxide and 1,4-diiodotetrafluorobenzene at 90 K [J].
Bianchi, R ;
Forni, A ;
Pilati, T .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2004, 60 :559-568
[7]  
Blessing R. H., 1989, Journal of Applied Crystallography, V22, P396, DOI 10.1107/S0021889889001639
[8]   2,6-dibromo-4-nitroaniline [J].
Bryant, R ;
James, SC ;
Norman, NC ;
Orpen, AG .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 :1113-1115
[9]   SOLID ADDUCTS OF HEXAMETHYLENETETRAMINE AND TRIHALOGENOMETHANES - CRYSTAL STRUCTURE OF 1-1 IODOFORM COMPOUND [J].
DAHL, T ;
HASSEL, O .
ACTA CHEMICA SCANDINAVICA, 1970, 24 (02) :377-&
[10]   SUPRAMOLECULAR SYNTHONS IN CRYSTAL ENGINEERING - A NEW ORGANIC-SYNTHESIS [J].
DESIRAJU, GR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (21) :2311-2327