2-(3,4-Dimeth­oxy­phen­yl)-1H-benzimidazole

Aliakbar Dehno Khalaji; Alireza Foroghnia; Mohammad Ali Khalilzadeh; Karla Fejfarová; Michal Dušek

doi:10.1107/S1600536811046897

. 2011 Nov 9;67(Pt 12):o3255. doi: 10.1107/S1600536811046897

2-(3,4-Dimethoxyphenyl)-1H-benzimidazole

Aliakbar Dehno Khalaji ^a, Alireza Foroghnia ^b, Mohammad Ali Khalilzadeh ^b, Karla Fejfarová ^c,^*, Michal Dušek ^c

PMCID: PMC3238911 PMID: 22199764

Abstract

In title compound, C₁₅H₁₄N₂O₂, the dihedral angle between the 3,4-dimethoxyphenyl group and the benzimidazole system is 26.47 (6)°. In the crystal, neighbouring molecules are linked by N—H⋯N hydrogen bonds into C(4) chains propagating along the c-axis direction. The crystal structure also features weak C—H⋯O interactions.

Related literature

For a related structure, further synthetic details and background references to imidazolines, see: Khalaji et al. (2008 ▶). For related structures, see: Kia et al. (2008 ▶, 2009 ▶); Rashid et al. (2007 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₂
M _r = 254.3
Orthorhombic,
a = 9.2274 (8) Å
b = 15.0109 (9) Å
c = 9.2681 (3) Å
V = 1283.74 (14) Å³
Z = 4
Cu Kα radiation
μ = 0.72 mm⁻¹
T = 120 K
0.40 × 0.21 × 0.09 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.75, T _max = 1
12506 measured reflections
1982 independent reflections
1919 reflections with I > 3σ(I)
R _int = 0.024

Refinement

R[F ² > 3σ(F ²)] = 0.026
wR(F ²) = 0.072
S = 1.46
1982 reflections
174 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.08 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046897/hb6490sup1.cif

e-67-o3255-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046897/hb6490Isup2.hkl

e-67-o3255-Isup2.hkl^{(78.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811046897/hb6490Isup3.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
C14—H14c⋯O2ⁱ	0.96	2.49	3.224 (2)	133
C15—H15b⋯O1ⁱⁱ	0.96	2.50	3.372 (2)	151
N1—H1⋯N2ⁱⁱⁱ	0.903 (19)	2.01 (2)	2.887 (2)	164.6 (16)

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

Acknowledgments

We acknowledge Golestan University and the Islamic Azad University, Qaemshahr, for partial support of this work, the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae Project of the Academy of Sciences of the Czech Republic.

supplementary crystallographic information

Comment

As part of our ongoing studies of imidazoline derivatives (Khalaji et al., 2008), we now report the synthesis and structure of the title compound, (I).

The dihedral angle between the N1/N2/C1—C7 and C8—C13 aromatic ring planes in (I) is 26.47 (6)°, which is comparable with related structures (Khalaji et al., 2008; Kia et al., 2008, 2009; Rashid et al., 2007). Atoms C14 and C15 in (I) are displaced from the mean plane of the C8—C13 ring by 0.1134 (17) Å and 0.1756 (18) Å, respectively.

In the crystal of (I), an N—H···N hydrogen bond links the molecules into chains propagating in [001] direction (Fig. 2). There are no aromatic π-π stacking interactions in (I) as the closest centroid-centroid separation of aromatic rings is 4.419 (1) Å, which contrasts with the situation in 2-(4-fluorophenyl)-1H-benzimidazole (Rashid et al., 2007) in which both N—H···N and π-π stacking help to establish the packing. The crystal structure of (I) is further stabilized by weak C—H···O interactions.

Experimental

The synthetic method used for the preparation of (I) was based on previous work (Khalaji et al., 2008), except that 3,4-dimethoxybenzaldehyde (2 mmol) was used. Light yellow slabs of (I) were obtained by evaporation of a methanol solution of (I) held at room temperature. Anal. Calc. for C₁₅H₁₄N₂O₂ (MW: 254.30): C, 70.85; H, 5.55; N, 11.01%. Found: C, 70.92; H, 5.65; N, 11.08%. Yield: 73%. IR (KBr pellet, cm-1): 2941, 2977, 3006 (CH aliphatic and aromatic), 3054 (s, –C—HN–), 1624 (s, C=N), 1504, 1588, 1606 (C—C aromatic). ¹H-NMR (500 MHz, CDCl3, δ(p.p.m.)): 3.82 (s, 3H), 3.87 (s, 3H), 7.11 (d, 1H), 7.17 (dd, 2H), 7.57 (s, 2H), 7.57–7.79 (m, 2H), 12.78 (s, 1H).