N′-[(E)-4-Benz­yloxy-2-hy­droxy­benzyl­idene]-4-nitro­benzohydrazide monohydrate

Bibitha Joseph; M Sithambaresan; M R Prathapachandra Kurup

doi:10.1107/S1600536812015401

. 2012 Apr 18;68(Pt 5):o1421–o1422. doi: 10.1107/S1600536812015401

N′-[(E)-4-Benzyloxy-2-hydroxybenzylidene]-4-nitrobenzohydrazide monohydrate

Bibitha Joseph ^a, M Sithambaresan ^b,^*, M R Prathapachandra Kurup ^a

PMCID: PMC3344544 PMID: 22590306

Abstract

The title compound, C₂₁H₁₇N₃O₅·H₂O, exists in the keto form with an E conformation with respect to the azomethine double bond. The twist angles between the aromatic rings are in the range 4.67 (10)–17.54 (10)°. A water molecule of solvation is present in the lattice. A conventional intramolecular O—H⋯N hydrogen bond increases the rigidity of the molecule. Intermolecular O—H⋯O, N—H⋯O and C—H⋯O hydrogen-bonding interactions establish a supramolecular linkage among the molecules in the crystal structure. There are also C—H⋯π interactions present.

Related literature

For the biological and other applications of carbohydrazides, see: Lakshmi et al. (2011 ▶); Grande et al. (2007 ▶); Naseema et al. (2010 ▶). For the synthesis, see: Emmanuel et al. (2011 ▶). For related structures of carbohydrazides, see: Fun et al. (2008 ▶). For the keto form, see: Bakir & Brown (2002 ▶).

Experimental

Crystal data

C₂₁H₁₇N₃O₅·H₂O
M _r = 409.39
Monoclinic,
a = 4.6275 (7) Å
b = 6.5332 (11) Å
c = 31.856 (5) Å
β = 92.417 (4)°
V = 962.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.30 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.969, T _max = 0.974
7388 measured reflections
1713 independent reflections
1663 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.088
S = 1.05
1713 reflections
288 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015401/fj2537sup1.cif

e-68-o1421-sup1.cif^{(26.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015401/fj2537Isup2.hkl

e-68-o1421-Isup2.hkl^{(84.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015401/fj2537Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C1–C6 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O1Sⁱ	0.86 (2)	2.57 (4)	3.058 (3)	117 (4)
O4—H4O⋯N3	0.86 (2)	1.93 (3)	2.670 (2)	143 (4)
N2—H2N⋯O1S	0.86 (2)	2.01 (2)	2.855 (3)	166 (3)
O1S—H2S⋯O4ⁱⁱ	0.87 (2)	2.01 (2)	2.860 (3)	165 (4)
O1S—H1S⋯O3ⁱⁱⁱ	0.88 (2)	1.80 (2)	2.676 (3)	175 (5)
C14—H14⋯O1S	0.93	2.37	3.184 (2)	146
C21—H21⋯O1S	0.93	2.43	3.325 (3)	161
C7—H7B⋯Cg^iv	0.97	2.69	3.472 (2)	138

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

BJ is grateful to the Council for Scientific and Industrial Research, New Delhi, India, for the award of a Senior Research Fellowship. The authors also thank the Sophisticated Analytical Instument Facility, Cochin University of Science & Technology, Kochi-22, for providing the single-crystal X-ray diffraction data.

supplementary crystallographic information

Comment

There is growing interest in the structural features of carbohydrazides as they show a wide range of biological activities, with potential uses in antibacterial, antifungal and anticancer studies (Lakshmi et al., 2011; Grande et al., 2007). Hydrazones and their metal complexes have found applications in chemical processes like non linear optics, sensors etc. (Naseema et al., 2010).

The title compound N'-{(E)-[4-(benzyloxy)-2-hydroxyphenyl]methylidene}-4-nitrobenzohydrazide hydrate is found to exist in the E configuration with respect to N3=C14 bond. A perspective view of the molecular structure of the title compound, along with the atom-labeling is shown in Fig. 1. The bond length of C15=O3 [1.229 (2) Å] shows a significant double-bond character (Fun et al.., 2008) indicating that the molecule exists in the keto form in the solid state (Bakir & Brown, 2002) and the dihedral angles between the aromatic rings are in the range of 4.67 (10) -17.54 (10)°.

The lattice water molecule plays an essential role in packing of the molecules forming conventional and non-conventional hydrogen bonds between the carbohydrazide and water molecules (Fig. 2). A C–H···π interaction is also observed in the crystal structure between one of the H atoms attached to the C7 carbon atom and the phenyl ring of the adjacent molecule in the crystal system (Fig. 3). Two types of very weak π–π interactions also present with a shortest centroid-centroid distance of 4.9302 (14) Å. In crystal packing, the parallel arrangement of the molecules along a axis is shown in Fig. 4.

Experimental

The title compound was prepared by adapting a reported procedure (Emmanuel et al., 2011) by refluxing a mixture of methanolic solutions of 4-nitrobenzohydrazide (0.181 g, 1 mmol) and 4-(benzyloxy)-2-hydroxybenzaldehyde (0.228 g, 1 mmol) for 4 h. The formed crystals were collected, washed with few drops of methanol and dried over P₄O₁₀in vacuo. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation from its methanolic solution.