1-(3-Meth­oxy­phen­yl)-4,5-dimethyl-2-phenyl-1H-imidazole

S Rizwana Begum; R Hema; N Srinivasan; A G Anitha

doi:10.1107/S1600536813016966

. 2013 Jun 26;69(Pt 7):o1154. doi: 10.1107/S1600536813016966

1-(3-Methoxyphenyl)-4,5-dimethyl-2-phenyl-1H-imidazole

S Rizwana Begum ^a, R Hema ^a,^*, N Srinivasan ^b, A G Anitha ^a

PMCID: PMC3770416 PMID: 24046701

Abstract

In the title compound, C₁₈H₁₈N₂O, the imidazole ring makes dihedral angles of 68.26 (7) and 22.45 (9)° with the methoxyphenyl and phenyl rings, respectively. The dihedral angle between the methoxyphenyl and phenyl ring is 71.86 (7)°. In the crystal, weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds link the molecules into columns propagated in [101].

Related literature

For related structures, see: Gayathri et al. (2010 ▶); Rosepriya et al. (2011 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₈H₁₈N₂O
M _r = 278.34
Triclinic,
a = 8.0199 (1) Å
b = 9.4807 (1) Å
c = 10.4971 (2) Å
α = 108.339 (1)°
β = 94.910 (1)°
γ = 90.535 (1)°
V = 754.27 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.974, T _max = 0.977
14252 measured reflections
2644 independent reflections
2159 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.148
S = 1.04
2644 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016966/cv5418sup1.cif

e-69-o1154-sup1.cif^{(19KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016966/cv5418Isup2.hkl

e-69-o1154-Isup2.hkl^{(127.2KB, hkl)}

Click here for additional data file.^{(6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813016966/cv5418Isup3.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
C5—H5A⋯O1ⁱ	0.96	2.57	3.316 (3)	135
C7—H7⋯N2ⁱⁱ	0.93	2.58	3.493 (2)	168

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

Acknowledgments

The authors are grateful to the SAIF, IIT Madras, for the data collection.

supplementary crystallographic information

Comment

In a continuation of structural studies of 4,5-dimethyl-1H-imidazole derivatives (Gayathri et al., 2010; Rosepriya et al., 2011), herewith we present the title compound, (I).

In (I) (Fig. 1), the imidazole ring is essentially planar [maximum deviation of 0.0036 (11) Å for N2 and -0.0036 (11) Å N1]. The imidazole ring makes dihedral angle of 68.26 (7)° and 22.45 (9)° with the methoxyphenyl (C6–C11) and phenyl (C13–C18) rings, respectively. The dihedral angle between the methoxyphenyl and phenyl rings is 71.86 (7)°.

The crystal structure is stabilized by weak C—H···O and C—H···N intermolecular interactions (Table 1). The C—H···O interactions link pairs of molecules across centres of inversion to give the ring motif R(16) (Bernstein et al., 1995). Atom C7 acts as a donor for a weak intermolecular C—H···N interaction via H7 with the nitrogen atom in the imidazole moiety, thus forming extended chains with a graph set motif C(6) (Bernstein et al., 1995).

Experimental

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), m-methoxy aniline (1.5 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and benzaldehyde (1.5 g, 15 mmol) was added about 1 h by maintaining the temperature at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by column chromatography using hexane: ethyl acetate as the eluent. Yield: 1.91 g (46%).