3-Methoxy­benzohydrazide

Rifat Ara Jamal; Uzma Ashiq; Muhammad Nadeem Arshad; Zahida Tasneem Maqsood; Islam Ullah Khan

doi:10.1107/S1600536809036526

. 2009 Sep 16;65(Pt 10):o2473. doi: 10.1107/S1600536809036526

3-Methoxybenzohydrazide

Rifat Ara Jamal ^a,^*, Uzma Ashiq ^a, Muhammad Nadeem Arshad ^b, Zahida Tasneem Maqsood ^a, Islam Ullah Khan ^b

PMCID: PMC2970484 PMID: 21577925

Abstract

The title compound, C₈H₁₀N₂O₂, crystallizes with two independent molecules in an asymmetric unit. The structure is stabilized by nine intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Ashiq, Jamal et al. (2008 ▶, 2009a ▶,b ▶); Jamal et al. (2008 ▶, 2009 ▶); Kallel et al. (1992 ▶); Saraogi et al. (2002 ▶). For the biological activity of hydrazides, see: Ara et al. (2007 ▶); Ashiq, Ara et al. (2008 ▶).

Experimental

Crystal data

C₈H₁₀N₂O₂
M _r = 166.18
Monoclinic,
a = 13.1288 (8) Å
b = 7.5417 (4) Å
c = 17.0734 (10) Å
β = 92.857 (3)°
V = 1688.40 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.39 × 0.15 × 0.11 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.979, T _max = 0.990
18386 measured reflections
4200 independent reflections
1708 reflections with I > 2σ(I)
R _int = 0.066

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.126
S = 0.95
4200 reflections
237 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.22 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. DOI: 10.1107/S1600536809036526/pv2207sup1.cif

e-65-o2473-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036526/pv2207Isup2.hkl

e-65-o2473-Isup2.hkl^{(205.8KB, 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
N11—H11N⋯N12ⁱ	0.91 (2)	2.12 (2)	2.958 (2)	153.3 (18)
N11—H11N⋯N11ⁱ	0.91 (2)	2.63 (2)	3.191 (2)	120.9 (13)
N12—H12N⋯O11ⁱⁱ	0.95 (2)	2.30 (2)	3.193 (2)	155.2 (18)
N12—H13N⋯N22ⁱⁱⁱ	0.85 (2)	2.47 (2)	3.185 (3)	142.6 (19)
N21—H21N⋯O11^iv	0.87 (2)	1.99 (2)	2.860 (2)	172 (2)
N22—H23N⋯O21^v	0.88 (2)	2.14 (2)	3.007 (2)	168 (2)
C18—H18C⋯O21^vi	0.96	2.58	3.498 (3)	160
C22—H22⋯O11^iv	0.93	2.35	3.208 (3)	153
C26—H26⋯O21^vii	0.93	2.56	3.439 (3)	157

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

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 constitute an important class of biologically active organic compounds (Ashiq, Ara et al., 2008; Ara et al., 2007). In searching for biologically active compounds we have synthesized the title compound, (I), and report its crystal structure in this paper.

The asymmetric unit of the title compound contains two crystallographically unique molecules (Fig. 1). The bond distances and bond angles in (I) are similar to the corresponding distances and angles reported in the structures of benzhydrazide (Kallel et al., 1992), para-chloro (Saraogi et al., 2002), para-bromo (Ashiq, Jamal et al., 2008),para-iodo (Jamal et al., 2008), para-methoxy (Ashiq, Jamal et al., 2009a), para-hydroxy (Jamal et al., 2009) and para-phenylsemicarbazide (Ashiq, Jamal et al., 2009b) analogues of (I).

In the crystal structure the molecules are held together by intermolecular hydrogen bonds of the types N—H···N, N—H···O and C—H···O (Table 1 and Fig. 2).

The title compound was found to be active against DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging and inactive against α-glucosidase enzyme (Ashiq, Ara et al., 2008).

Experimental

All reagent-grade chemicals were obtained from Aldrich and Sigma Chemical companies and were used without further purification. To a solution of ethyl-3-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 (I) (yield 79%). Crystal of the title compound suitable for X-ray crystallographic study were grown from a solution of methanol by slow evaporation at room temperature.