Abstract
In the asymmetric unit of the title compound {systematic name: 3-chloro-N-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,6-dinitro-4-(trifluoromethyl)aniline}, C13H4Cl2F6N4O4, which is the fungicide fluazinam, the dihedral angle between the pyridine and benzene ring planes is 42.20 (4)°. In the crystal, pairs of N—H⋯F hydrogen bonds link the molecules into inversion dimers which are linked by C—Cl⋯π [Cl⋯ring centroid = 3.3618 (4) A °] and N—O⋯π [O⋯ring centroid = 3.1885 (16) Å] interactions into chains along [100]. In addition, short Cl⋯Cl, O⋯Cl, and F⋯F contacts [3.4676 (7), 3.2371 (13) and 2.7910 (15) Å] are present which connect the chains, yielding a three-dimensional network.
Highlights
In the asymmetric unit of the title compound {systematic name: 3-chloro-N-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]2,6-dinitro-4-(trifluoromethyl)aniline}, C13H4Cl2F6N4O4, which is the fungicide fluazinam, the dihedral angle between the pyridine and benzene ring planes is 42.20 (4)
Pairs of N—HÁ Á ÁF hydrogen bonds link the molecules into inversion dimers which are linked by C—ClÁ Á Á [ClÁ Á Áring centroid = 3.3618 (4) A ] and N—OÁ Á Á [OÁ Á Áring centroid = 3.1885 (16) A ] interactions into chains along [100]
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2230)
Summary
In the asymmetric unit of the title compound {systematic name: 3-chloro-N-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]2,6-dinitro-4-(trifluoromethyl)aniline}, C13H4Cl2F6N4O4, which is the fungicide fluazinam, the dihedral angle between the pyridine and benzene ring planes is 42.20 (4). Pairs of N—HÁ Á ÁF hydrogen bonds link the molecules into inversion dimers which are linked by C—ClÁ Á Á [ClÁ Á Áring centroid = 3.3618 (4) A ] and N—OÁ Á Á [OÁ Á Áring centroid = 3.1885 (16) A ] interactions into chains along [100]. Short ClÁ Á ÁCl, OÁ Á ÁCl, and FÁ Á ÁF contacts [3.4676 (7), 3.2371 (13) and 2.7910 (15) A ] are present which connect the chains, yielding a three-dimensional network. Related literature For information on the toxicity and fungicidal properties of the title compound, see: Yoshida & Yukimoto (1993); Draper et al (2003). See: McCullough et al (1972)
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