4-Methoxy­benzohydrazide

Uzma Ashiq; Rifat Ara Jamal; Muhammad Nawaz Tahir; Sammer Yousuf; Islam Ullah Khan

doi:10.1107/S1600536809021345

. 2009 Jun 10;65(Pt 7):o1551. doi: 10.1107/S1600536809021345

4-Methoxybenzohydrazide

Uzma Ashiq ^a,^*, Rifat Ara Jamal ^a, Muhammad Nawaz Tahir ^b, Sammer Yousuf ^c, Islam Ullah Khan ^d

PMCID: PMC2969388 PMID: 21582836

Abstract

The title compound, C₈H₁₀N₂O₂, is stabilized by three intermolecular hydrogen bonds of the N—H⋯O and N—H⋯N types. Two intramolecular interactions of the N—H⋯O and C—H⋯O types are also observed.

Related literature

For related structures see: Ashiq, Jamal et al. (2008 ▶); Jamal et al. (2008 ▶), Kallel et al. (1992 ▶); Saraogi et al. (2002 ▶); For the biological activity of hydrazides, see: Ara et al. (2007 ▶); Ashiq, Ara et al. (2008 ▶); El-Emam et al. (2004 ▶); Maqsood et al. (2006 ▶).

Experimental

Crystal data

C₈H₁₀N₂O₂
M _r = 166.18
Orthorhombic,
a = 3.9887 (1) Å
b = 6.1487 (2) Å
c = 32.8919 (9) Å
V = 806.68 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.22 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.979, T _max = 0.992
17597 measured reflections
1288 independent reflections
1052 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.147
S = 1.03
1288 reflections
119 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021345/pv2163sup1.cif

e-65-o1551-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021345/pv2163Isup2.hkl

e-65-o1551-Isup2.hkl^{(62.3KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.83 (4)	2.16 (4)	2.961 (3)	162 (3)
N2—H2A⋯O1	0.92 (5)	2.42 (4)	2.729 (2)	100 (3)
N2—H2A⋯O1ⁱⁱ	0.92 (5)	2.44 (4)	3.026 (2)	122 (3)
N2—H2B⋯O1ⁱⁱⁱ	0.93 (4)	2.07 (4)	2.991 (2)	170 (4)
C7—H7⋯O1	0.93	2.47	2.781 (3)	100

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

Acknowledgments

The authors thank the Higher Education Commission Pakistan for providing the diffractometer at GCU, Lahore, and BANA International for their support in collecting the crystallographic data.

supplementary crystallographic information

Comment

Hydrazides are known to have different biological activities and have been used for the synthesis of various heterocyclic compounds (El-Emam et al., 2004). The title compound was found to be antileishmanial, antibacterial and antifungal (Maqsood et al., 2006). Vanadium complex of the title compound was found to ba a good inhibitor of urease (Ara et al., 2007) and alpha-glucosidase (Ashiq, Ara et al., 2008). In order to study the biological behaviour of 4-methoxybenzhydrazide and to investigate the change in activity due to complexation with vanadium center, we have synthesized (I) and report its crystal structure in this paper. The structures of benzhydrazide (Kallel et al., 1992), para-chloro (Saraogi et al., 2002), para-bromo (Ashiq, Jamal et al., 2008) and para-iodo (Jamal et al., 2008) analogues of (I) have already been reported.

The crystal structure of the title compound is presented in Fig. 1. The bond distances and bond angles in (I) are similar to the corresponding distances and angles reported in the structures quoted above. The phenyl group (C2—C7) and hydrazide moiety, O1/N1/N2/C1, in (I) are each planar with a dihedral angle between their least square planes being 7.08 (14)%. In the crystal structure, the molecules of I are linked by the N1—H1···N2, N2—H2A···O1 and N2—H2B···O1 intermolecular hydrogen bonds to form chains (details are given in Table 1, Fig 2). The geometry of 4-methoxybenzhydrazide is stabilized by N2—H2A···O1 and C7—H7···O1 intramolecular hydrogen interactions.

Experimental

All reagent-grade chemicals were obtained from Aldrich and Sigma Chemical companies and were used without further purification. To a solution of ethyl-4-methoxybenzoate (3.6 g, 20 mmol) in 75 ml ethanol, hydrazine hydrate (5.0 ml, 100 mmol) was added. The mixture was refluxed for 5 h and a solid was obtained upon removal of the solvent by rotary evaporation. The resulting solid was washed with hexane to afford 4-methoxybenzhydrazide (yield 64%). (Maqsood et al., 2006).