BenzylN-(1-{N′-[(E)-2-chlorobenzylidene]hydrazinecarbonyl}-2-hydroxyethyl)carbamate

Marcus V N De Souza,Alessandra C Pinheiro,James L Wardell,Edward R T Tiekink,Solange M S V Wardell

doi:10.1107/s1600536811024895

Marcus V N De Souza, Alessandra C Pinheiro + Show 3 more

Open Access

https://doi.org/10.1107/s1600536811024895

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Abstract

The molecule of the title compound, C18H18ClN3O4, is twisted about the chiral C atom with the dihedral angle between the two amide residues being 87.8 (5)°, but, overall, it can be described as curved, with the benzene rings lying on the same side of the molecule [dihedral angle = 62.8 (4)°]. The conformation about the imine bond [1.294 (7) Å] is E. In the crystal, a two-dimensional array in the ab plane is mediated by O—H⋯O and N—H⋯O hydrogen bonds as well as C—H⋯Cl interactions. The layers stack along the c-axis direction, being connected by C—H⋯.π contacts.

Highlights

Fundação Oswaldo Cruz, Instituto de Tecnologia, em Fármacos – Farmanguinhos, R
H atoms treated by a mixture of independent and constrained refinement max = 0.38 e Å3
The molecule of the title compound, C18H18ClN3O4, is twisted about the chiral C atom with the dihedral angle between the two amide residues being 87.8 (5), but, overall, it can be described as curved, with the benzene rings lying on the same side of the molecule [dihedral angle = 62.8 (4) ]

Summary

Data collection

Fundação Oswaldo Cruz, Instituto de Tecnologia, em Fármacos – Farmanguinhos, R. Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, b. CHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, and dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil. H atoms treated by a mixture of independent and constrained refinement max = 0.38 e Å3. R factor = 0.070; wR factor = 0.196; data-to-parameter ratio = 14.1. The molecule of the title compound, C18H18ClN3O4, is twisted about the chiral C atom with the dihedral angle between the two amide residues being 87.8 (5) , but, overall, it can be described as curved, with the benzene rings lying on the same side of the molecule [dihedral angle = 62.8 (4) ]. The layers stack along the c-axis direction, being connected by C—H . contacts

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