4-[Amino­(3-methyl­phen­yl)methyl­idene]-2-(3-methyl­phen­yl)-1H-imidazol-5(4H)-one ethanol hemisolvate

M Prabhuswamy; S Madan Kumar; C P Muneer; P M Shafi; N K Lokanath

doi:10.1107/S160053681205163X

. 2013 Jan 4;69(Pt 2):o174. doi: 10.1107/S160053681205163X

4-[Amino(3-methylphenyl)methylidene]-2-(3-methylphenyl)-1H-imidazol-5(4H)-one ethanol hemisolvate

M Prabhuswamy ^a, S Madan Kumar ^a, C P Muneer ^b, P M Shafi ^b, N K Lokanath ^a,^*

PMCID: PMC3569236 PMID: 23424459

Abstract

In the title compound, C₁₈H₁₇N₃O·0.5C₂H₅OH, the dihedral angles between the central imidazole rings and the pendant benzene rings are 42.06 (15) and 2.01 (16)° in one asymmetric molecule and 47.91 (15) and 7.31 (14)° in the other. An intramolecular N—H⋯O hydrogen bond occurs in each imidazole molecule. In the crystal, the components are connected by O—H⋯N, N—H⋯O, C—H⋯O and N—H⋯N hydrogen bonds. Weak aromatic π–π interactions also occur [shortest centroid–centroid distance = 3.684 (3) Å].

Related literature

For background to imidazoles, see: Shi et al. (2011 ▶). For a related structure, see: Chang et al. (2012 ▶). For further synthetic details, see: Shafi et al. (2005 ▶).

Experimental

Crystal data

C₁₈H₁₇N₃O·0.5C₂H₆O
M _r = 314.38
Triclinic,
a = 8.227 (4) Å
b = 13.505 (7) Å
c = 16.044 (8) Å
α = 87.451 (8)°
β = 78.869 (9)°
γ = 80.241 (9)°
V = 1723.6 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 300 K
0.23 × 0.22 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer
16691 measured reflections
6512 independent reflections
4294 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.227
S = 1.02
6512 reflections
430 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: Mercury.

Supplementary Material

Click here for additional data file.^{(41.3KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681205163X/hb7015sup1.cif

e-69-0o174-sup1.cif^{(41.3KB, cif)}

Click here for additional data file.^{(318.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205163X/hb7015Isup2.hkl

e-69-0o174-Isup2.hkl^{(318.7KB, hkl)}

Click here for additional data file.^{(7.1KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681205163X/hb7015Isup3.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
N3B—H3B1⋯O1B	0.86	2.07	2.748 (3)	135
O2—H2⋯N1B	1.09	1.84	2.917 (3)	170
N3B—H3B2⋯N1A	0.86	2.37	3.033 (3)	134
N2A—H2A⋯O1A ⁱ	0.86	1.95	2.803 (3)	170
N2B—H2B⋯O1B ⁱⁱ	0.86	1.97	2.805 (3)	164
N3A—H3A1⋯O1A	0.86	2.12	2.783 (3)	134
N3A—H3A2⋯O2ⁱⁱⁱ	0.86	2.02	2.857 (3)	163
C12A—H12A⋯O1A ⁱ	0.93	2.59	3.492 (4)	164
C12B—H12B⋯O1B ⁱⁱ	0.93	2.54	3.455 (3)	168
C16B—H16B⋯O2	0.93	2.37	3.284 (4)	168

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

Acknowledgments

SMK thanks UGC–BRS and the University of Mysore for the award of a fellowship.

supplementary crystallographic information

Comment

Imidazole derivatives exhibits various bioactivities (Shi et al., 2011). As part of our studies in the area, we now report the structure of the title solvate, (I).

The asymmetric unit consists of two symmetry-independent molecules (A and B) of the title compound and the solvent molecule (ethanol) as shown in Fig. 1. The conformations of the two molecules are almost same which is confirmed by the dihedral angles [42.72 (14)° and 41.46 (15)° between aromatic rings of molecule A and molecule B, respectively]. The geometry of the compound is similar to (Z)-4-(2-Hydroxybenzylidene)-1-methyl-2-phenyl-1H-imidazol-5(4H)-one (Chang et al., 2012).

The molecules are connected by hydrogen bonds of the type N—H···O, C—H···O and N—H···N (Fig. 2.). Table 1 shows the geometry of intramolecular and intermolecular hydrogen bond. In addition, weak interactions π—π occur [shortest centroid-centroid distance = 3.684 (3) Å].

Experimental

The title molecule was synthesized according to the reported procedure (Shafi et al., 2005) and yellow blocks were recrystallized from ethanol solution.