Intermolecular interactions in two (ferrocenylmethyl)benzimidazoles incorporating the 4-MeOC6H4 and 3,4-(MeO)2C6H3 groups:: analysis of MeO-C-C distortions from ideal 120° geometry

被引:21
作者
Gallagher, JF [1 ]
Hanlon, K [1 ]
Howarth, J [1 ]
机构
[1] Dublin City Univ, Sch Chem Sci, Dublin 9, Ireland
关键词
D O I
10.1107/S0108270101015591
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title compounds, 1-ferrocenylmethyl-2-(4-methoxyphenyl)-1H-benzimidazole, [Fe(C5H5)(C20H17N2O)], (I), and 2-(3,4-dimethoxyphenyl)-1-ferrocenylmethyl-1H-benzimidazole, [Fe(C5H5)(C21H19N2O2)], (II), are model electroactive compounds for anion sensor and antimalarial applications. Distortions from the ideal 120 degrees angle about the MeO-C-C groups are evident, with angles of 115.1 (2) and 125.0 (2)degrees in (I), and 115.9 (2) and 124.6 (2)degrees, and 115.7 (2) and 125.1 (2)degrees in (II). The main intermolecular hydrogen bonds in (I) comprise C-H . . .N and C-H . . . pi (C5H5) interactions, while in (II), only weak C-H . . . pi (imidazole) and C-H . . . pi (arene) interactions are present.
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页码:1410 / 1414
页数:5
相关论文
共 37 条
[1]  
ALLEN FH, 1993, CHEM DESIGN AUTOMATI, V8, P1
[2]   CHEMISTRY AND CRYSTAL-STRUCTURES OF SOME CONSTITUENTS OF ZINGIBER-CASSUMUNAR [J].
AMATAYAKUL, T ;
CANNON, JR ;
DAMPAWAN, P ;
DECHATIWONGSE, T ;
GILES, RGF ;
HUNTRAKUL, C ;
KUSAMRAN, K ;
MOKKHASAMIT, M ;
RASTON, CL ;
REUTRAKUL, V ;
WHITE, AH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (01) :71-88
[3]   Transition-metal receptor systems for the selective recognition and sensing of anionic guest species [J].
Beer, PD .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (02) :71-80
[4]   REACTION OF FERROCENECARBALDEHYDE WITH O-PHENYLENEDIAMINE - CRYSTAL-STRUCTURE OF N-FERROCENYLMETHYL-2-FERROCENYL-BENZIMIDAZOLE [J].
BENITO, A ;
MARTINEZMANEZ, R ;
PAYA, J ;
SOTO, J ;
TENDERO, MJL ;
SINN, E .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 503 (02) :259-263
[5]   N-heterocyclic carbenes with N-ferrocenyl-N′-methyl-substitution:: synthesis, reactivity, structure and electrochemistry [J].
Bildstein, B ;
Malaun, M ;
Kopacka, H ;
Ongania, KH ;
Wurst, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 572 (02) :177-187
[6]   Imidazoline-2-ylidene metal complexes with pendant ferrocenyl substituents [J].
Bildstein, B ;
Malaun, M ;
Kopacka, H ;
Ongania, KH ;
Wurst, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 552 (1-2) :45-61
[7]   4,5-Dihydro-7,8-dimethoxy-1-phenyl-3H-2,3-benzodiazepin-4-one [J].
Bruno, G ;
Nicoló, F ;
Rotondo, A ;
Gitto, R ;
Zappalá, M .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2001, 57 :1225-1227
[8]  
Burnett M.N., 1996, ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations
[9]   ISOTHIAZOLES .2. REACTION OF 3-DIETHYLAMINO-4-(4-METHOXYPHENYL)-ISOTHIAZOLE-1,1-DIOXIDE WITH SODIUM-AZIDE [J].
CARUGO, O ;
CLERICI, F ;
POCAR, D .
TETRAHEDRON, 1993, 49 (40) :9117-9126
[10]   Brucinium hydrogen fumarate sesquihydrate and brucinium hydrogen maleate [J].
Dijksma, FJJ ;
Gould, RO ;
Parsons, S ;
Walkinshaw, MD .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 :1948-1951