3-Meth­oxy-4-[3-(2-methyl-4-nitro-1H-imidazol-1-yl)prop­oxy]benzaldehyde

Lei Jin; Guang-Zhou Wang; Cheng-He Zhou

doi:10.1107/S1600536809031894

. 2009 Aug 15;65(Pt 9):o2164. doi: 10.1107/S1600536809031894

3-Methoxy-4-[3-(2-methyl-4-nitro-1H-imidazol-1-yl)propoxy]benzaldehyde

Lei Jin ^a,^b, Guang-Zhou Wang ^a, Cheng-He Zhou ^a,^*

PMCID: PMC2969872 PMID: 21577572

Abstract

In the title molecule, C₁₅H₁₇N₃O₅, the dihedral angle between the benzene and imidazole rings is 3.69 (2)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds and π–π stacking interactions with a centroid–centroid distance of 3.614 (1) Å.

Related literature

For general background to the biological activity of nitroimidazole and its derivatives, see:Demirayak et al. (1999 ▶); Huang et al. (2007 ▶); Olender et al. (2009 ▶). For the synthetic procedure, see: Khalafi-Nezhad et al. (2005 ▶).

Experimental

Crystal data

C₁₅H₁₇N₃O₅
M _r = 319.32
Monoclinic,
a = 9.4885 (14) Å
b = 13.048 (2) Å
c = 12.745 (2) Å
β = 101.120 (3)°
V = 1548.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.28 × 0.24 × 0.2 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.971, T _max = 0.979
7761 measured reflections
3329 independent reflections
2329 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.130
S = 1.03
3329 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031894/lh2876sup1.cif

e-65-o2164-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031894/lh2876Isup2.hkl

e-65-o2164-Isup2.hkl^{(163.3KB, hkl)}

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
C4—H4B⋯O4ⁱ	0.98	2.58	3.415 (3)	144
C8—H8⋯O4ⁱⁱ	0.95	2.51	3.229 (2)	133
C10—H10B⋯O2ⁱⁱⁱ	0.99	2.56	3.312 (2)	133
C10—H10A⋯O1^iv	0.99	2.58	3.461 (2)	148
C14—H14⋯O1^iv	0.95	2.29	3.166 (2)	153

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

Acknowledgments

We thank Southwest University (SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (2007BB5369) for financial support.

supplementary crystallographic information

Comment

Nitroimidazole and its derivatives possess several biological activities such as radiosensitizer, anti-tuberculosis and antimicrobial (Demirayak et al., 1999; Huang et al., 2007; Olender et al., 2009). In view of the therapeutic potentials of nitroimidazole derivatives, we are interested in the research and development of nitroimidazole compounds as drugs. Herein we report the crystal structure of the title compound (I).

The stucture of the title compound (I) is shown in Fig 1. In the molecule the dihedral angle between the benzene and imidazole rings is 3.69 (2)°. The crystal structure is stabilized by weak intermolecular C—H···O hydrogen bonds and significant π–π stacking interactions with a centroid to centroid ditance of 3.614 (1)Å between benzene and imidazole rings related by the symmetry operator (1/2-x, 1/2+y, 1/2-z).

Experimental

Compound (I) was synthesized according to the procedure of Khalafi-Nezhad et al. (2005). Single crystals used in X-ray diffraction studies were grown by slow evaporation at room temperature of solutions of (I) in ethyl acetate and dichlormethane mixtures.