N′-[(E)-1-(4-Bromo­phen­yl)ethyl­idene]-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide

Hoong-Kun Fun; Ching Kheng Quah; Priya V Frank; N Damodara; Balakrishna Kalluraya

doi:10.1107/S160053681202795X

. 2012 Jun 23;68(Pt 7):o2192. doi: 10.1107/S160053681202795X

N′-[(E)-1-(4-Bromophenyl)ethylidene]-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Priya V Frank ^b,^c, N Damodara ^c, Balakrishna Kalluraya ^b

PMCID: PMC3393992 PMID: 22798857

Abstract

In the title compound, C₁₄H₁₄BrN₅O₃, the mean plane of the imidazole ring (r.m.s deviation = 0.004 Å) forms a dihedral angle of 58.13 (7)° with the benzene ring. In the crystal, molecules are linked via N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds into a three-dimensional network. A short Br⋯Br contact of 3.4932 (2) Å also occurs.

Related literature

For general background to and applications of imidazole derivatives, see: Priya & Kalluraya (2005 ▶); Krapcho & Turk (1966 ▶); Chu et al. (2004 ▶); Khalafi-Nezhad et al. (2005 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₄H₁₄BrN₅O₃
M _r = 380.21
Monoclinic,
a = 8.4176 (1) Å
b = 10.6541 (1) Å
c = 17.4933 (2) Å
β = 90.100 (1)°
V = 1568.83 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.64 mm⁻¹
T = 100 K
0.37 × 0.33 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.441, T _max = 0.701
45099 measured reflections
6320 independent reflections
5026 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.082
S = 1.02
6320 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202795X/rz2774sup1.cif

e-68-o2192-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202795X/rz2774Isup2.hkl

e-68-o2192-Isup2.hkl^{(309.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681202795X/rz2774Isup3.cml

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
N2—H1N2⋯O1ⁱ	0.81 (2)	2.04 (2)	2.8318 (14)	166.6 (18)
C9—H9A⋯O3ⁱⁱ	0.99	2.31	3.1818 (16)	147
C9—H9B⋯N4ⁱⁱⁱ	0.99	2.40	3.3462 (16)	160
C10—H10A⋯O2ⁱⁱ	0.95	2.56	3.4488 (16)	155

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

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for an Incentive Grant.

supplementary crystallographic information

Comment

The chemistry of imidazole derivatives has been the subject of much interest due to their importance in various applications and also due to their widespread potential as well as proven biological and pharmacological activities (Priya & Kalluraya, 2005). Various applications of imidazoles have been listed in the literature with functions as widely divergent as antidepressant agents (Krapcho & Turk, 1966), as a marker for imaging tumor hypoxia( Chu et al., 2004), and in antibacterial activity (Khalafi-Nezhad et al., 2005). In view of the obvious importance of imidazole derivatives as potential pharmacological agents, herein we report the crystal structure of the above imidazole derivative.

In the title molecule, Fig. 1, the mean plane of the imidazole ring (N3/N4/C10-C12, r.m.s deviation = 0.004 Å) forms a dihedral angle of 58.13 (7)° with the phenyl ring (C1-C6). Bond lengths (Allen et al., 1987) and angles are within normal ranges. A short Br1···Br1 contact of 3.4932 (2) Å also occurs. In the crystal (Fig. 2), molecules are linked via intermolecular N2–H1N2···O1, C9–H9A···O3, C9–H9B···N4 and C10–H10A···O2 hydrogen bonds (Table 1) into a three-dimensional network.

Experimental

The title compound was synthesized by refluxing a mixture of 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acethydrazide (0.1 mol) and 1-(4-bromophenyl)ethanone (0.1 mol) in glacial acetic acid for 1 hour. After cooling the reaction mixture to room temperature and evaporation of the solvent under reduced pressure, the solid separated was filtered, washed with water and dried. The recrystallization of the sample was done using an ethanol-dioxane (1:1 v/v) mixture. The melting point of the compound was found to be 549 K. The slow evaporation of the ethanol-dioxane mixture of the compound gave crystals suitable for X-ray analysis.