2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl methane­sulfonate

Sammer Yousuf; Aurang Zeb; Farhana Batool; Fatima Z Basha

doi:10.1107/S1600536812034964

. 2012 Aug 25;68(Pt 9):o2781. doi: 10.1107/S1600536812034964

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl methanesulfonate

Sammer Yousuf ^a,^*, Aurang Zeb ^a, Farhana Batool ^a, Fatima Z Basha ^a,^‡

PMCID: PMC3435813 PMID: 22969659

Abstract

The asymmetric unit of the title compound, C₇H₁₁N₃O₅S, contains two independent molecules with virtually identical conformations. The imidazole rings of both molecules are essentially planar (r.m.s. deviations = 0.0019 and 0.0038 Å), with a dihedral angle 9.25 (19)° between them. The nitro groups are oriented at 4.5 (2) and 6.44 (13)° with respect to the imidazole rings. In the crystal, molecules are linked to form a three-dimensional framework by C—H⋯O and C—H⋯N hydrogen bonds.

Related literature

For the biological activity of metronidazole, see: Zeb, Malik et al. (2012 ▶). For related structures, see: Yousuf et al. (2012 ▶); Zeb, Yousuf et al. (2012 ▶).

Experimental

Crystal data

C₇H₁₁N₃O₅S
M _r = 249.26
Triclinic,
a = 8.8547 (17) Å
b = 10.927 (2) Å
c = 12.033 (2) Å
α = 112.702 (4)°
β = 100.614 (4)°
γ = 90.052 (4)°
V = 1052.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 273 K
0.40 × 0.21 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.883, T _max = 0.975
11649 measured reflections
3918 independent reflections
3078 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.152
S = 1.07
3918 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.32 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034964/pv2579sup1.cif

e-68-o2781-sup1.cif^{(29.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034964/pv2579Isup2.hkl

e-68-o2781-Isup2.hkl^{(192KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034964/pv2579Isup3.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—H5B⋯O6ⁱ	0.97	2.50	3.235 (4)	133
C5—H5C⋯N7ⁱⁱ	0.97	2.54	3.484 (4)	165
C7—H7B⋯O9ⁱⁱⁱ	0.96	2.59	3.498 (4)	157
C7—H7C⋯O10^iv	0.96	2.52	3.423 (4)	157
C12—H12A⋯O1^v	0.97	2.50	3.250 (5)	134
C12—H12B⋯N3^vi	0.97	2.53	3.472 (4)	164
C14—H14B⋯O5^vii	0.96	2.59	3.507 (4)	160
C14—H14C⋯O4^viii	0.96	2.55	3.414 (4)	150

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .

supplementary crystallographic information

Comment

Metronidazole (Flagyl) is a well known broad spectrum antibiotic. The structural analogues of metronidazole are reported to have a wide range of biological activities including antibacterial anticancer, antiglycation and H. pylori urease inhibitors (Zeb, Malik et al., 2012). The title compound is a methanesulfonate derivative of metronidazole, synthesized as a part of our ongoing reaserch to synthesize and evaluate the antiglycation potential and establish structure activity relationship of the structural analogues of metronidazole.

The title compound contains two independent molecules in an asymmetric unit (Fig. 1) with identical conformations. The two imidazole rings (C2—C4/N2/N3 and C9—C11/N5/N7) are individually planar with r.m.s.d's 0.0038 and 0.0019 Å, respectively; the dihedral angle between the mean planes of the imidazole rings is 9.25 (19)°. The nitro groups N1/O1/O2 and N4/O6/O7 are oriented at 4.5 (2) and 6.44 (13)° with respect to the imidazole rings (C2—C4/N2/N3) and (C9—C11/N5/N7), respectively. The bond distances and angles in both molecules of the title compound agree very well with the corresponding bond distances and angles reported in closely related compounds (Yousuf et al., 2012; Zeb et al., 2012). The crystal packing (Fig. 2) is consolidated by weak intermolecular C—H···O and C—H···N type hydrogen bonds (Table 1).

Experimental

The title compound was synthesized by adding methane sulfonyl chloride (16 mmol) drop wise into an ice-cooled solution of metronidazole (10 mmol) and triethylamine (16 mmol) in dry dichloromethane (DCM) with continuous stirring. The reaction mixture was further stirred in the ice bath for 4 h. The separated thick material was filtered and washed with water (20 ml X 3) to obtain a cream coloured solid which was dissolved and recrystallized from DCM by slow evaporation to give pure crystals of the title compound (82% yield), suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma–Aldrich.