1-{(E)-[3-(1H-Imidazol-1-yl)-1-phenyl­propyl­idene]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/S1600536812022659

. 2012 May 23;68(Pt 6):o1848–o1849. doi: 10.1107/S1600536812022659

1-{(E)-[3-(1H-Imidazol-1-yl)-1-phenylpropylidene]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: PMC3379417 PMID: 22719615

Abstract

In the title compound, C₂₀H₂₁N₅O, the conformation about the imine bond [1.289 (3) Å] is E. Overall, the molecule is disk-shaped with the imidazole ring located above the remainder of the molecule and with the dihedral angles of 10.97 (15) and 12.11 (15)°, respectively, between the imidazole ring and the phenyl and methylbenzene rings; the dihedral angle between the aromatic rings is 8.17 (14)°. Within the urea unit, the N—H atoms are anti to each other and one of the N—H atoms forms an intramolecular N—H⋯N hydrogen bond. Helical supramolecular chains along [001] are formed via N—H⋯N(imidazole) hydrogen bonds in the crystal structure. These are connected into a three-dimensional architecture by C—H⋯O(carbonyl) and C—H⋯π interactions.

Related literature

For background to 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-o1848-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₁N₅O
M _r = 347.42
Orthorhombic,
a = 20.5220 (17) Å
b = 14.1916 (11) Å
c = 6.0060 (4) Å
V = 1749.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.40 × 0.08 × 0.04 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.805, T _max = 1.000
8422 measured reflections
2211 independent reflections
1809 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.097
S = 1.02
2211 reflections
244 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 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/S1600536812022659/mw2069sup1.cif

e-68-o1848-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022659/mw2069Isup2.hkl

e-68-o1848-Isup2.hkl^{(108.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022659/mw2069Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C10–C15 and N4,N5,C18–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N3	0.88 (1)	2.12 (3)	2.601 (3)	114 (2)
N2—H2n⋯N5ⁱ	0.89 (1)	2.03 (1)	2.884 (3)	161 (3)
C5—H5⋯O1ⁱⁱ	0.95	2.49	3.416 (3)	164
C7—H7B⋯Cg1ⁱⁱⁱ	0.98	2.82	3.686 (3)	148
C12—H12⋯Cg1^iv	0.95	2.72	3.464 (3)	135
C20—H20⋯Cg2ⁱ	0.95	2.85	3.604 (3)	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

The title compound, (2E)-2-[3-(1H-imidazol-1-yl)-1-phenylpropylidene]-N-(2-methylphenyl)hydrazinecarboxamide (I) will be evaluated as anti-convulsant in experimental animal models for which structural information is desirable. The motivation for its study is the observation that aryl semicarbazones can exhibit significant anti-convulsant activities (Aboul-Enein et al., 2012; Dimmock et al., 1995; Dimmock et al., 1993). Epilepsy is one of the most widespread pathologies of human brain, affecting approximately 1% of world population (Sander & Shorvon, 1987). The need for new drugs arises as currently used 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 therapies (Saxena & Saxena, 1995). Aside from that, many anti-epileptics used clinically cause significant side-effects (Edafiogho & Scott, 1996).

In (I), Fig. 1, the conformation about the N3═C9 bond [1.289 (3) Å] is E. The dihedral angles between the imidazolyl ring and the phenyl and methylbenzene rings are 10.97 (15) and 12.11 (15)°, respectively; the dihedral angle between the phenyl and benzene rings is 8.17 (14)°. Overall, the main part of the molecule, excepting the imidazolyl substituent, appears flat and is significantly flatter than the recently determined 4-methoxybenzene analogue (Attia et al., 2012). Within the urea moiety, the N—H atoms are anti to each other and the N1—H atom forms an intramolecular N—H···N hydrogen bond which defines a S(5) loop, Table 1.

In the crystal structure, helical supramolecular chains along [001] are formed via N—H···N(imidazolyl) hydrogen bonds, Fig. 2 and Table 1. These are connected into a three-dimensional architecture by C—H···O(carbonyl) and 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-phenyl-propan-1-one (0.20 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 solution was concentrated under vacuum and the precipitated solid was filtered off. The collected solid was recrystallized from ethanol to give crystals of the title compound; M.P.: 453–455 K.