(E)-3-Chloro-N′-hydroxybenzene-1-carboximidamide

Abstract

The title compound, C7H7ClN2O, crystallizes with two independent mol­ecules in the asymmetric unit. The compound adopts an E configuration across the C=N double bond, as the –OH group and the benzene ring are on opposite sides of the double bond while the H atom of the hy­droxy group is directed away from the –NH2 group. In the crystal, mol­ecules are linked to one another through O—H⋯N and N—H⋯O hydrogen bonds, forming chains along [010].

N′-Hydroxypyridine-2-carboximidamide

“…The title compound, (I), crystalizes with a single molecule in the asymmetric unit. This is in contrast to (E)-3-chloro-N′hydroxybenzene-1-carboximidamide, (II), (Sreenivasa et al, 2012) which crystalizes with two molecules in its asymmetric unit. Compound (I) adopts an E configuration across the C=N double bond, as the OH group and the benzene ring are on opposite sides of the double bond, while the H atom of the hydroxy group is directed away from the NH 2 group.…”

“…For the pharmaceutical and biological activity of substituted N 0 -hydroxybenzamidines and 1,2,4-oxadiazole derivatives, see: Kundu et al (2012); Sakamoto et al (2007); Tyrkov & Sukhenko (2004). For a related structure, see: Sreenivasa et al (2012) Experimental Crystal data…”

Crystal structures ofN-(3-fluorobenzoyl)benzenesulfonamide andN-(3-fluorobenzoyl)-4-methylbenzenesulfonamide

“…A comparison of the dihedral angle between the two benzene rings in these closely related structures indicates that introducing a methyl substituent into the para position of the benzenesulfonyl ring lowers the dihedral angle with compound (VII) being an exception. The dihedral angle values are 80.3 (1) in (III) (Gowda et al, 2009a), 87.5 (1) in (IV) (Gowda et al, 2009b), 83.3 (2), 84.4 (2) and 87.6 (2) in the three molecules of (V) (Suchetan et al, 2012), 79.4 (1) in (VI) (Suchetan et al, 2010) and 89.6 (2) in (VII) (Sreenivasa et al, 2014). This effect is the same as that observed in the present two structures (I) and (II).…”

“…Further, N-(arylsulfonyl)arylamides are known to be potent antitumour agents against a broad spectrum of human tumour xenografts (colon, lung, breast, ovary and prostate) in nude mice (Mader et al, 2005). As part of our ongoing work on the synthesis and crystal structures of this class of compound (Gowda et al, 2009a,b;Sreenivasa et al, 2014;Suchetan et al, 2010Suchetan et al, , 2012, compounds (I) and (II) were synthesized and their crystal structures were determined.…”