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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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A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines and C—H⋯π inter­actions are represented as red arrows (see Table 1 ▸ for further details).
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fig3: A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines and C—H⋯π inter­actions are represented as red arrows (see Table 1 ▸ for further details).

Mentions: In the crystal of (I), the amide carbonyl O-atom, O1, shows bifurcated hydrogen bonding (Table 1 ▸ and Fig. 2 ▸); one with the hydrazide hydrogen atom and the other with one of the hydrogen atoms of the water mol­ecule (O3). The two hydrogen atoms of the water mol­ecule are involved in hydrogen bonding with the O atoms of the amide carbonyl (O3—H31⋯O1) and glycine carbonyl (O3—H32⋯O2) groups of two different mol­ecules of the title compound. The O atom is also involved in hydrogen bonding with the H atom of the carbonyl­amide group of a third symmetry-related mol­ecule (N1—H1N⋯O3). A pair of N2—H2N⋯O1 inter­molecular hydrogen bonds link the mol­ecules, forming inversion dimers, with an (14) ring motif. The dimers are further linked via hydrogen bonds involving the water mol­ecule generating (14) and (18) ring motifs. Further, the N2—H2N⋯O1 and N1—H1N⋯O3 hydrogen bonds between the mol­ecules of the main compound and water mol­ecules translate into (6) chains along the a-axis direction (Table 1 ▸ and Fig. 2 ▸) The chains are linked by a C—H⋯O inter­action, forming sheets parallel to (010). Within the sheets there are C—H⋯π, and parallel slipped π–π stacking inter­actions [Cg2⋯Cg2i = 3.6458 (12) Å; inter-planar distance = 3.4135 (8) Å, slippage = 1.281 Å; Cg2 is the centroid of ring C11–C16; symmetry code: (i) −x + 1, −y + 1, −z + 1] involving inversion-related chloro­benzene rings; see Fig. 3 ▸.


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)

A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines and C—H⋯π inter­actions are represented as red arrows (see Table 1 ▸ for further details).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig3: A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines and C—H⋯π inter­actions are represented as red arrows (see Table 1 ▸ for further details).
Mentions: In the crystal of (I), the amide carbonyl O-atom, O1, shows bifurcated hydrogen bonding (Table 1 ▸ and Fig. 2 ▸); one with the hydrazide hydrogen atom and the other with one of the hydrogen atoms of the water mol­ecule (O3). The two hydrogen atoms of the water mol­ecule are involved in hydrogen bonding with the O atoms of the amide carbonyl (O3—H31⋯O1) and glycine carbonyl (O3—H32⋯O2) groups of two different mol­ecules of the title compound. The O atom is also involved in hydrogen bonding with the H atom of the carbonyl­amide group of a third symmetry-related mol­ecule (N1—H1N⋯O3). A pair of N2—H2N⋯O1 inter­molecular hydrogen bonds link the mol­ecules, forming inversion dimers, with an (14) ring motif. The dimers are further linked via hydrogen bonds involving the water mol­ecule generating (14) and (18) ring motifs. Further, the N2—H2N⋯O1 and N1—H1N⋯O3 hydrogen bonds between the mol­ecules of the main compound and water mol­ecules translate into (6) chains along the a-axis direction (Table 1 ▸ and Fig. 2 ▸) The chains are linked by a C—H⋯O inter­action, forming sheets parallel to (010). Within the sheets there are C—H⋯π, and parallel slipped π–π stacking inter­actions [Cg2⋯Cg2i = 3.6458 (12) Å; inter-planar distance = 3.4135 (8) Å, slippage = 1.281 Å; Cg2 is the centroid of ring C11–C16; symmetry code: (i) −x + 1, −y + 1, −z + 1] involving inversion-related chloro­benzene rings; see Fig. 3 ▸.

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