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

Bibitha Joseph; M Sithambaresan; M R Prathapachandra Kurup

doi:10.1107/S1600536813017091

. 2013 Jun 26;69(Pt 7):o1160–o1161. doi: 10.1107/S1600536813017091

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

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

PMCID: PMC3770421 PMID: 24046706

Abstract

The title compound, C₂₁H₁₇N₃O₅·C₃H₇NO, exists in an E conformation with respect to the azomethine double bond of the hydrazide molecule. This molecule contains an intramolecular O—H⋯N hydrogen bond, while an intermolecular N—H⋯O hydrogen bond links the hydrazide to the formamide molecule of solvation. Nonclassical C—H⋯O intermolecular hydrogen bonds build up a supramolecular architecture, together with two C—H⋯π interactions and a weak π–π interaction, with a centroid–centroid distance of 3.650 (13) Å.

Related literature

For the biological and analytical applications of carbohydrazides, see: Vicini et al. (2002 ▶); Savini et al. (2002 ▶); Grande et al. (2007 ▶). For the synthesis of related compounds, see: Mathew & Kurup (2011 ▶); Despaigne et al. (2009 ▶). For related structures, see: Joseph et al. (2012 ▶). graphic file with name e-69-o1160-scheme1.jpg

Experimental

Crystal data

C₂₁H₁₇N₃O₅·C₃H₇NO
M _r = 464.47
Monoclinic,
a = 10.0160 (8) Å
b = 22.661 (2) Å
c = 10.2611 (11) Å
β = 101.392 (5)°
V = 2283.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.977, T _max = 0.981
16107 measured reflections
4910 independent reflections
2901 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.176
S = 1.04
4910 reflections
318 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.22 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, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017091/fj2634sup1.cif

e-69-o1160-sup1.cif^{(30.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017091/fj2634Isup2.hkl

e-69-o1160-Isup2.hkl^{(240.5KB, hkl)}

Click here for additional data file.^{(8.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813017091/fj2634Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O6	0.88 (1)	1.95 (1)	2.810 (3)	166 (2)
O2—H2O⋯N1	0.85 (1)	1.82 (2)	2.583 (2)	149 (3)
C7—H7B⋯O3ⁱ	0.97	2.49	3.167 (3)	127
C13—H13⋯O1ⁱⁱ	0.93	2.58	3.448 (3)	156
C21—H21⋯O6	0.93	2.42	3.206 (3)	143
C12—H12⋯Cg1ⁱⁱ	0.93	2.91	3.673 (2)	140
C17—H17⋯Cg1ⁱ	0.93	2.85	3.630 (3)	142

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

Acknowledgments

BJ is grateful to the Council for Scientific and Industrial Research, New Delhi, India, for the award of a Senior Research Fellowship. MRPK is grateful to UGC, New Delhi, for a UGC-BSR one-time grant to Faculty. The authors are grateful to Dr Matthias Zeller, Department of Chemistry, Youngstown State University, for the support with data refinement. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India for the single-crystal X-ray diffraction measurements.

supplementary crystallographic information

Comment

Coordination chemistry and biochemistry of hydrazones have received increasing interest due to their chelating ability and their antimicrobial, antituberculosis and antitumour activities (Vicini et al. 2002; Savini et al., 2002; Grande et al. 2007). As a continuous work on the hydrazide compounds, a new hydrazide compound, N'-[(E)-4-Benzyloxy-2-hydroxybenzylidene]-4-nitrobenzohydrazide dimethylformamide monosolvate, was prepared and structurally characterized.

The compound crystallizes in monoclinic space group P2₁/c. This molecule adopts an E configuration (Fig.1) with respect to C14—N1 bond with torsional angles of 177.93 (18)°. The title compound exists in amido form with C15—O3 bond length of 1.217 (3) Å, which is very close to C═O bond length of a similar reported nitrobenzohydrazide compound (Joseph et al., 2012). The aromatic ring (C1–C6) of the compound forms dihedral angles between the other two aromatic rings (C8–C13 and C16–C21) with angles of 67.63 (12) and 61.58 (12)° respectively. There are one classical N2—H2'···O6 and three non-classical C—H···O intermolecular hydrogen bonds (Fig. 2) present in the molecular system with D···A distances of 2.810 (3), 3.167 (3), 3.448 (3) and 3.206 (3) Å (Table 1) respectively. These intermolecular hydrogen bonds chain the molecules along c axis. Moreover, two C—H···π interactions between the H atoms attached at the C12 and C17 atoms and the corresponding aromatic ring C1–C6 of the neighbouring molecules with H···π distances of 3.673 (2) and 3.630 (3) Å respectively, also support the hydrogen bonding to form a one-dimensional layer along c axis. This supramolecular network is augmented by a weak π–π interaction (Fig. 2) between the phenyl rings (C8–C13 and C16–C21) of the molecules with a centroid–centroid distance of 3.650 (13) Å by interconnecting the molecules along b axis. Packing of molecules is predominantly favored by the classical intermolecular hydrogen bonding and C—H···π interactions. Other short ring interactions are very weak as they correspond to their centroid-centroid distances greater than 4 Å. Intramolecular classical hydrogen bond is also observed in the molecular system (Table 1). Fig. 3 shows the packing diagram of the title compound along c axis.

Experimental

The title compound was prepared by adapting a reported procedure (Mathew & Kurup, 2011; Despaigne et al., 2009). A methanolic solution of 4-nitrobenzohydrazide (0.181 g, 1 mmol) was added to a solution of 4-(benzyloxy)-2-hydroxybenzldehyde (0.228 g, 1 mmol) in ethanol and the reaction mixture was refluxed for 5 h after adding a few drops of dilute sulfuric acid. On cooling yellow colored 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 recrystallization from a mixture of ethanol and dimethylformamide (1:1 v/v).