1-{(E)-[3-(1H-Imidazol-1-yl)-1-(4-meth­oxy­phen­yl)propyl­idene]amino}-3-(2-methyl­phen­yl)urea

Mohamed I Attia; Mohamed N Aboul-Enein; Nasser R El-Brollosy; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812021903

. 2012 May 19;68(Pt 6):o1799–o1800. doi: 10.1107/S1600536812021903

1-{(E)-[3-(1H-Imidazol-1-yl)-1-(4-methoxyphenyl)propylidene]amino}-3-(2-methylphenyl)urea

Mohamed I Attia ^a,^b,^‡, Mohamed N Aboul-Enein ^b, Nasser R El-Brollosy ^a, Seik Weng Ng ^c,^d, Edward R T Tiekink ^c,^*

PMCID: PMC3379375 PMID: 22719573

Abstract

In the title compound, C₂₁H₂₃N₅O₂, the conformation about the imine bond [1.287 (3) Å] is E. Overall, the molecule has a disk shape, the dihedral angles between the imidazole ring and the methoxyphenyl and methylphenyl rings being 49.42 (13) and 42.62 (13)°, respectively; the dihedral angle between the benzene rings is 20.11 (11)°. In the urea moiety, the N—H atoms are anti to each other and one of these forms an intramolecular N—H⋯N hydrogen bond. In the crystal, centrosymmetric dimers are formed via N—H⋯N(imidazole) hydrogen bonds, which are connected into a three-dimensional architecture by C—H⋯O(carbonyl) and (methylene)C—H⋯π interactions. The crystal studied was a non-merohedral twin with a minor component of 48.3 (1)%.

Related literature

For background to the prevalence of epilepsy and epilepsy drugs, see: Sander & Shorvon (1987 ▶); Saxena & Saxena (1995 ▶); Edafiogho & Scott (1996 ▶). For the use of aryl semicarbazones as anti-convulsants, see: Aboul-Enein et al. (2012 ▶); Dimmock et al. (1993 ▶, 1995 ▶). For a related structure, see: Attia et al. (2012 ▶). graphic file with name e-68-o1799-scheme1.jpg

Experimental

Crystal data

C₂₁H₂₃N₅O₂
M _r = 377.44
Monoclinic,
a = 10.7798 (12) Å
b = 20.7750 (19) Å
c = 8.7652 (18) Å
β = 105.318 (15)°
V = 1893.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.15 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.692, T _max = 1.000
15110 measured reflections
7494 independent reflections
4657 reflections with I > 2σ(I)
R _int = 0.080

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.216
S = 0.98
7494 reflections
263 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021903/gg2079sup1.cif

e-68-o1799-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021903/gg2079Isup2.hkl

e-68-o1799-Isup2.hkl^{(366.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812021903/gg2079Isup3.cml

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

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

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N3	0.87 (3)	2.04 (2)	2.568 (3)	118 (2)
N2—H2n⋯N5ⁱ	0.87 (3)	2.17 (3)	3.029 (3)	171 (2)
C16—H16B⋯O1ⁱⁱ	0.98	2.44	3.398 (3)	165
C20—H20⋯O1ⁱ	0.95	2.51	3.226 (3)	133
C17—H17A⋯Cg2ⁱⁱⁱ	0.99	2.80	3.391 (3)	119
C18—H18B⋯Cg3^iv	0.99	2.78	3.569 (2)	137

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

Acknowledgments

The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

Epilepsy is one of the most widespread pathologies of the human brain, affecting approximately 1% of world population (Sander & Shorvon, 1987). Current anti-epileptic drugs suffer from a number of disadvantages including the fact that approximately one quarter of epileptic patients have seizures that are resistant to the available medical therapy (Saxena & Saxena, 1995). Additionally, many clinically used anti-epileptic drugs cause significant side-effects which may limit their usefulness (Edafiogho & Scott, 1996). Accordingly, the evolution of novel anti-convulsants is a continuing challenge. An evaluation of the literature revealed that aryl semicarbazones were found to exhibit significant anti-convulsant activities (Aboul-Enein et al., 2012; Dimmock et al., 1995; Dimmock et al., 1993). The novel title compound, namely (2E)-2-[3-(1H-imidazol-1-yl)-1-(4-methoxphenyl)propylidene]-N-(2-methylphenyl)hydrazinecarboxamide (I) will be evaluated as anti-convulsant in experimental animal models. Herein, we describe the results of its crystal structure determination.

In (I), Fig. 1, the conformation about the N3═C9 bond [1.287 (3) Å] is E. The dihedral angles between the imidazolyl ring and the methoxy- and methyl-benzene rings are 49.42 (13) and 42.62 (13)°, respectively; the dihedral angle between the benzene rings is 20.11 (11)°. Despite these angles of inclination, overall the molecule as a disk which contrasts the flat topology in the non-methoxy species (Attia et al., 2012). The methoxy group is co-planar with the benzene ring to which it is attached as seen in the value of the C16—O2—C13—C12 torsion angle of -173.1 (2)°. Within the urea moiety, the N—H atoms are anti to each other and the N1—H forms an intramolecular N—H···N hydrogen bond to define a S(5) loop, Table 1.

In the crystal structure, centrosymmetric dimers are formed via N—H···N(imidazolyl) hydrogen bonds and 18-membered {···HNNC₃NCN}₂ synthons, Fig. 2 and Table 1. These aggregates are connected into a three-dimensional architecture by C—H···O(carbonyl) and (methylene)C—H···π interactions, Fig. 3 and Table 1.

Experimental

Acetic acid (2 drops) was added to a stirred solution of 3-(1H-imidazol-1-yl)-1-(4-methoxyphenyl)propan-1-one (0.23 g, 1 mmol) and N-(2-methylphenyl)hydrazinecarboxamide (0.17 g, 1 mmol) in absolute ethanol (10 ml). The reaction mixture was stirred at room temperature for 18 h. The solvent was concentrated under reduced pressure and the precipitated solid was collected by filtration. The collected solid was recrystallized from ethanol to give crystals of the title compound; Mp: 363–365 K.