Abstract
The title compound, C10H11ClN2O2, features an almost planar Car—N(H)—N=C(Cl) unit [torsion angle = 0.8 (1)° whose phenyl substituent is almost coplanar with it [dihedral angle = 2.8 (2)°]; this unit is slightly twisted with respect to the carboxyl –CO2 fragment [dihedral angle = 10.3 (2)°]. In the crystal, the amino group acts as a hydrogen-bond donor to the carbonyl O atom of an adjacent molecule; the hydrogen bond generates a helical chain that runs along the b axis of the monoclinic unit cell.
Highlights
The title compound, C10H11ClN2O2, features an almost planar Car—N(H)—N C(Cl) unit [torsion angle = 0.8 (1) whose phenyl substituent is almost coplanar with it [dihedral angle = 2.8 (2)]; this unit is slightly twisted with respect to the carboxyl –CO2 fragment [dihedral angle = 10.3 (2)]
The amino group acts as a hydrogen-bond donor to the carbonyl O atom of an adjacent molecule; the hydrogen bond generates a helical chain that runs along the b axis of the monoclinic unit cell
Related literature For a review of the reactions of hydrazonyl halides with heterocyclic thiones for heteroannulation, the synthesis of spiroheterocycles and heterocyclic ring formation, see: Shawali & Farghaly (2008)
Summary
Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 A; R factor = 0.026; wR factor = 0.076; data-to-parameter ratio = 17.1. The amino group acts as a hydrogen-bond donor to the carbonyl O atom of an adjacent molecule; the hydrogen bond generates a helical chain that runs along the b axis of the monoclinic unit cell. Related literature For a review of the reactions of hydrazonyl halides with heterocyclic thiones for heteroannulation, the synthesis of spiroheterocycles and heterocyclic ring formation, see: Shawali & Farghaly (2008). See: Xu (2006); Yin et al (2006)
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