N-(4-Chlorophenyl)ethanimidamide

A twisted conformation is found in the title compound, C8H9ClN2, with the ethanimidamide residue being twisted substantially to the benzene ring [dihedral angle = 66.54 (14)°]. The conformation about the C=N double bond [1.299 (3) Å] is Z. A two-dimensional array with a zigzag topology is formed in the crystal structure via N—H⋯N and N—H⋯Cl hydrogen-bonding interactions.

A twisted conformation is found in the title compound, C 8 H 9 ClN 2 , with the ethanimidamide residue being twisted substantially to the benzene ring [dihedral angle = 66.54 (14) ]. The conformation about the C N double bond [1.299 (3) Å ] is Z. A two-dimensional array with a zigzag topology is formed in the crystal structure via N-HÁ Á ÁN and N-HÁ Á ÁCl hydrogen-bonding interactions.
The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES and FAPEMIG (Brazil). Comment N-(p-Chlorophenyl)acetamidine and related N-arylacetamidines (Shearer et al. 1997;Rousselet et al. 1993;Patai, 1975) were synthesized for use as reagents in the formation of 5-(difluoromethyl)-2-methyl-1-(substituted-phenyl)-1H-imidazoles, which are active anti-leishmanial compounds (Ferreira et al., 2007). Leishmaniasis is caused by several species of protozoan parasites transmitted by the bite of the female phlebotomine sand fly. This neglected disease is currently prevalent in four continents, being endemic in 88 countries, 72 of which are developing countries, threatening 350 millions worldwide (World Health Organization, 2010). The treatment of Leishmaniasis, currently, is dependent on old and highly toxic drugs (Croft et al., 2006). In addition, the development of clinical resistance and the increase of co-infections leishmaniasis AIDS, in some countries is causing further worries. Thus, the development of new, efficient, and safe drugs for the treatment of this disease is imperative (Ouellette et al., 2004;Croft et al., 2006;Ferreira et al., 2007). This contribution describes the synthesis and crystallographic characterisation of an N-(p-chlorophenyl)acetamidine derivative, (I).
The molecular structure of (I), Fig. 1, is twisted about the C1-N1 bond as seen in the value of the C2-C1-N1-C7 torsion angle of -118.6 (2) °; the dihedral angle formed between the benzene ring and ethanimidamide residue is 66.54 (14)  supplementary materials sup-2
The positions of the N-H atoms were refined with U iso (H) = 1.2U eq (N). Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Figures
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )