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Crystal structure of (E)-N-{2-[2-(2-chloro-benzyl-idene)hydrazin-1-yl]-2-oxoeth-yl}-4-methyl-benzamide monohydrate.

Purandara H, Foro S, Gowda BT - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The dimers are linked by O-H⋯O hydrogen bonds, involving two mol-ecules of water, forming chains along [100], enclosing R 2 (2)(14) and R 2 (2)(18) ring motifs.The chains are linked through C-H⋯O inter-actions, forming sheets parallel to (010).Within the sheets, there are C-H⋯π and parallel slipped π-π stacking inter-actions present [inter-centroid distance = 3.6458 (12) Å].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India.

ABSTRACT
The title compound, C17H16ClN3O2·H2O, an acyl-hydrazone derivative, contains a glycine moiety and two substituted benzene rings on either end of the chain. It crystallized as a monohydrate. The mol-ecules adopt an E conformation with respect to the C=N double bond, as indicated by the N-N=C-C torsion angle of 179.38 (14)°. The mol-ecule is twisted in such a way that the almost planar Car-C(=O)-N(H)-C(H2) and C(H2)-C(=O)N(H)-N=C-Car [r.m.s deviations = 0.009 and 0.025 Å, respectively] segments are inclined to on another by 77.36 (8)°, while the benzene rings are normal to one another, making a dihedral angle of 89.69 (9)°. In the crystal, the water mol-ecule links three mol-ecules through two O-H⋯O and one N-H⋯O hydrogen bonds. The mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(14) ring motif. The dimers are linked by O-H⋯O hydrogen bonds, involving two mol-ecules of water, forming chains along [100], enclosing R 2 (2)(14) and R 2 (2)(18) ring motifs. The chains are linked through C-H⋯O inter-actions, forming sheets parallel to (010). Within the sheets, there are C-H⋯π and parallel slipped π-π stacking inter-actions present [inter-centroid distance = 3.6458 (12) Å].

No MeSH data available.


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The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
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fig1: The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Mentions: The title compound crystallizes as a monohydrate (Fig. 1 ▸). The conformation of the N—H bond in the amide part is anti with respect to both the C=O bonds in the mol­ecule, while the N—H bond in the hydrazone part is syn to both the C=O(hydrazone) and the C—H(imine) bonds. The C9—O2 bond length of 1.2251 (19) Å indicates that the mol­ecule exists in the keto form in the solid state, and the C10—N3 bond length of 1.271 (2) Å confirms its significant double-bond character. The C9—N2 and N2—N3 bond distances of 1.351 (2) and 1.3771 (18) Å, respectively, indicate a significant delocalization of the π-electron density over the hydrazone portion of the mol­ecule. Variations in the C—N bond lengths of 1.330 (2), 1.442 (2) and 1.351 (2) Å for C7—N1, C8—N1 and C9—N2, respectively, characterize mobility of the bridge and the integral flexibility of the –C(=O)–NH–CH2C(=O)–NH–N=CH– group connecting the two benzene rings. The mol­ecule is twisted at atom C8, the C7—N1—C8—C9 torsion angle being 79.8 (2)°. The hydrazone part of the mol­ecule is almost planar, with C9—N2—N3—C10 and N2—N3—C10—C11 torsion angles of −177.07 (15) and 179.38 (14)°, respectively. Further, the dihedral angle between the almost planar hydrazone segment (O2/N2/N3/C8–C11; maximum deviation of 0.029 (1) Å for atom N2) and the attached benzene ring (C11–C16) is 8.17 (6)°. The two benzene rings (C1–C6 and C11–C16) are orthogonal to each other, making a dihedral angle of 89.69 (9)°. The planar amide segment (O1/N1/C1/C7/C8; r.m.s. deviation = 0.009 Å) is inclined to the attached toluene ring (C1–C6) by 8.06 (9) Å.


Crystal structure of (E)-N-{2-[2-(2-chloro-benzyl-idene)hydrazin-1-yl]-2-oxoeth-yl}-4-methyl-benzamide monohydrate.

Purandara H, Foro S, Gowda BT - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518978&req=5

fig1: The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Mentions: The title compound crystallizes as a monohydrate (Fig. 1 ▸). The conformation of the N—H bond in the amide part is anti with respect to both the C=O bonds in the mol­ecule, while the N—H bond in the hydrazone part is syn to both the C=O(hydrazone) and the C—H(imine) bonds. The C9—O2 bond length of 1.2251 (19) Å indicates that the mol­ecule exists in the keto form in the solid state, and the C10—N3 bond length of 1.271 (2) Å confirms its significant double-bond character. The C9—N2 and N2—N3 bond distances of 1.351 (2) and 1.3771 (18) Å, respectively, indicate a significant delocalization of the π-electron density over the hydrazone portion of the mol­ecule. Variations in the C—N bond lengths of 1.330 (2), 1.442 (2) and 1.351 (2) Å for C7—N1, C8—N1 and C9—N2, respectively, characterize mobility of the bridge and the integral flexibility of the –C(=O)–NH–CH2C(=O)–NH–N=CH– group connecting the two benzene rings. The mol­ecule is twisted at atom C8, the C7—N1—C8—C9 torsion angle being 79.8 (2)°. The hydrazone part of the mol­ecule is almost planar, with C9—N2—N3—C10 and N2—N3—C10—C11 torsion angles of −177.07 (15) and 179.38 (14)°, respectively. Further, the dihedral angle between the almost planar hydrazone segment (O2/N2/N3/C8–C11; maximum deviation of 0.029 (1) Å for atom N2) and the attached benzene ring (C11–C16) is 8.17 (6)°. The two benzene rings (C1–C6 and C11–C16) are orthogonal to each other, making a dihedral angle of 89.69 (9)°. The planar amide segment (O1/N1/C1/C7/C8; r.m.s. deviation = 0.009 Å) is inclined to the attached toluene ring (C1–C6) by 8.06 (9) Å.

Bottom Line: The dimers are linked by O-H⋯O hydrogen bonds, involving two mol-ecules of water, forming chains along [100], enclosing R 2 (2)(14) and R 2 (2)(18) ring motifs.The chains are linked through C-H⋯O inter-actions, forming sheets parallel to (010).Within the sheets, there are C-H⋯π and parallel slipped π-π stacking inter-actions present [inter-centroid distance = 3.6458 (12) Å].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India.

ABSTRACT
The title compound, C17H16ClN3O2·H2O, an acyl-hydrazone derivative, contains a glycine moiety and two substituted benzene rings on either end of the chain. It crystallized as a monohydrate. The mol-ecules adopt an E conformation with respect to the C=N double bond, as indicated by the N-N=C-C torsion angle of 179.38 (14)°. The mol-ecule is twisted in such a way that the almost planar Car-C(=O)-N(H)-C(H2) and C(H2)-C(=O)N(H)-N=C-Car [r.m.s deviations = 0.009 and 0.025 Å, respectively] segments are inclined to on another by 77.36 (8)°, while the benzene rings are normal to one another, making a dihedral angle of 89.69 (9)°. In the crystal, the water mol-ecule links three mol-ecules through two O-H⋯O and one N-H⋯O hydrogen bonds. The mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(14) ring motif. The dimers are linked by O-H⋯O hydrogen bonds, involving two mol-ecules of water, forming chains along [100], enclosing R 2 (2)(14) and R 2 (2)(18) ring motifs. The chains are linked through C-H⋯O inter-actions, forming sheets parallel to (010). Within the sheets, there are C-H⋯π and parallel slipped π-π stacking inter-actions present [inter-centroid distance = 3.6458 (12) Å].

No MeSH data available.


Related in: MedlinePlus