N′-[(E)-4-(Dimethyl­amino)­benz­ylidene]-2-(5-meth­oxy-2-methyl-1H-indol-3-yl)acetohydrazide

Shaaban K Mohamed; Peter N Horton; Mehmet Akkurt; Mustafa R Albayati; Antar A Abdelhamid

doi:10.1107/S1600536812026013

. 2012 Jun 13;68(Pt 7):o2099. doi: 10.1107/S1600536812026013

N′-[(E)-4-(Dimethylamino)benzylidene]-2-(5-methoxy-2-methyl-1H-indol-3-yl)acetohydrazide

Shaaban K Mohamed ^a, Peter N Horton ^b, Mehmet Akkurt ^c,^*, Mustafa R Albayati ^d, Antar A Abdelhamid ^a

PMCID: PMC3393912 PMID: 22798777

Abstract

In the title compound, C₂₁H₂₄N₄O₂, inversion-related molecules are linked into dimers through pairs of N—H⋯O hydrogen bonds, which generate R ₂ ²(8) motifs. As well as dimer formation, an additional N—H⋯O hydrogen bond and two C—H⋯π contacts, involving H atoms from the phenyl ring and the pyrrole and benzene rings of the indole system, generate a three-dimensional network.

Related literature

For the biological activity of indole acetic acid derivatives and indomethacin, see: Klassen (2001 ▶); Kirnura & Doi (1998 ▶); Rossiter et al. (2002 ▶); Shahab et al. (2009 ▶). For related structures, see: Trask et al. (2004 ▶); Gelbrich et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₁H₂₄N₄O₂
M _r = 364.44
Monoclinic,
a = 9.600 (5) Å
b = 7.548 (4) Å
c = 25.802 (14) Å
β = 95.10 (1)°
V = 1862.2 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.10 × 0.01 × 0.01 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001 ▶) T _min = 0.992, T _max = 0.999
10458 measured reflections
3280 independent reflections
2386 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.159
S = 1.15
3280 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear (Rigaku, 2001 ▶); data reduction: CrystalClear; 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: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026013/sj5239sup1.cif

e-68-o2099-sup1.cif^{(28.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026013/sj5239Isup2.hkl

e-68-o2099-Isup2.hkl^{(160.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812026013/sj5239Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the N1/C1–C3/C8 and C3–C8 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.88	2.21	2.984 (3)	147
N2—H2⋯O1ⁱⁱ	0.88	1.97	2.854 (3)	179
C18—H18⋯Cg2ⁱⁱⁱ	0.95	2.84	3.692 (4)	151
C19—H19⋯Cg1ⁱⁱⁱ	0.95	2.72	3.508 (4)	141

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

Acknowledgments

The authors are grateful to the Higher Education Ministry of Iraq for financial support. They also thank Manchester Metropolitan University and the UK National Crystallography Service, University of Southampton, for supporting this study.

supplementary crystallographic information

Comment

Indole-3-acetic acid (IAA) is the main auxin in plants, controlling many important physiological processes including cell enlargement and division, tissue differentiation, and responses to light and gravity (Shahab et al., 2009). In addition, derivatives of substituted indole-acetic acid are active oxidative pro-drugs with potential of cancer therapy (Rossiter et al., 2002). Indomethacin is an example of IAA derivatives exhibits anti-inflammatory, analgesic, and antipyretic properties and is therefore used to treat acute and chronic pain (Klassen, 2001; Kirnura & Doi, 1998). As part of our interest in production of potential pharmaceutical active compounds based on well known pharmacophores e.g indomethacin, we are herein reporting the synthesis and crystal structure of the title compound.

In the title molecule (I), Fig. 1, the 1H-indole system (N1\C1—C8) is essentially planar [maximum deviation -0.025 (3) Å for atom C1] and makes a dihedral angle of 73.65 (12) ° with the (C14–C19) benzene ring. The bond lengths and angles are normal and comparable to those observed in the related structures (Trask et al., 2004; Gelbrich et al., 2007).

In the crystal structure, molecules form a dimer, in which a pair of N1—H1···O2 hydrogen bonds generate an intermolecular R₂²(8) ring (Bernstein, et al., 1995; Table 1, Fig. 2). These dimers are further linked by the N2—H2···O1 hydrogen bonds. Two additional C—H···π interactions also contribute to an extensive three dimensional network (Table 1).

Experimental

A solution of 341 mg (1 mmol) 2-{1-[(4-chlorophenyl)carbonyl]-2-methyl-1H-indol-3-yl}acetohydrazide in 30 ml ethanol was added to a solution of 149 mg (1 mmol) 4-(dimethylamino)benzaldehyde in 20 ml ethanol in presence of few drops of catalytic glacial acetic acid and refluxed at 350 K for 6 h. On evaporating the excess solvent, a mass solid product was collected, washed with cold ethanol and dried. The crude product was recrystallized from ethanol to afford the title compound in a good yield (77%). Pure crystals suitable for X-ray diffraction were grown by slow evaporation of ethanol solution of the product at room temperature (m.p. 381 K).