2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl methane-sulfonate.

The asymmetric unit of the title compound, C(7)H(11)N(3)O(5)S, contains two independent mol-ecules with virtually identical conformations. The imidazole rings of both mol-ecules 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, mol-ecules 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 = 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

Δρmax = 0.79 e Å−3

Δρmin = −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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536812034964/pv2579Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H11N3O5S	Z = 4
Mr = 249.26	F(000) = 520
Triclinic, P1	Dx = 1.573 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8547 (17) Å	Cell parameters from 3658 reflections
b = 10.927 (2) Å	θ = 2.4–27.9°
c = 12.033 (2) Å	µ = 0.32 mm−1
α = 112.702 (4)°	T = 273 K
β = 100.614 (4)°	Plate, colorles
γ = 90.052 (4)°	0.40 × 0.21 × 0.08 mm
V = 1052.4 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	3918 independent reflections
Radiation source: fine-focus sealed tube	3078 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scan	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.883, Tmax = 0.975	k = −13→13
11649 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0914P)2 + 0.2849P] where P = (Fo2 + 2Fc2)/3
3918 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.09144 (8)	−0.18810 (7)	0.47184 (7)	0.0370 (2)
S2	0.60576 (8)	0.68767 (7)	0.52683 (7)	0.0356 (2)
O1	−0.2081 (3)	0.3132 (3)	0.8913 (3)	0.0621 (7)
O2	−0.1805 (3)	0.1027 (2)	0.8395 (2)	0.0557 (6)
O3	0.1479 (2)	−0.1063 (2)	0.61360 (19)	0.0384 (5)
O4	−0.0597 (2)	−0.1572 (2)	0.4331 (2)	0.0475 (6)
O5	0.2124 (3)	−0.1640 (2)	0.4178 (2)	0.0524 (6)
O6	0.0876 (2)	0.1903 (2)	0.1110 (2)	0.0526 (6)
O7	0.1462 (2)	0.4013 (2)	0.1692 (2)	0.0493 (6)
O8	0.5899 (2)	0.60582 (19)	0.38527 (18)	0.0365 (5)
O9	0.7537 (2)	0.6633 (2)	0.5805 (2)	0.0498 (6)
O10	0.4738 (2)	0.6572 (2)	0.5663 (2)	0.0474 (6)
N1	−0.1298 (3)	0.2166 (3)	0.8633 (2)	0.0398 (6)
N2	0.1317 (2)	0.1471 (2)	0.8363 (2)	0.0301 (5)
N3	0.2445 (3)	0.3407 (2)	0.8613 (2)	0.0423 (6)
N4	0.1824 (3)	0.2858 (2)	0.1409 (2)	0.0348 (6)
N5	0.4575 (2)	0.3517 (2)	0.1632 (2)	0.0288 (5)
N7	0.5555 (3)	0.1572 (2)	0.1374 (3)	0.0433 (6)
C1	0.4070 (4)	0.1507 (4)	0.8164 (3)	0.0507 (8)
H1A	0.4842	0.2158	0.8222	0.076*
H1B	0.3896	0.0805	0.7359	0.076*
H1C	0.4415	0.1144	0.8770	0.076*
C2	0.2630 (3)	0.2136 (3)	0.8381 (3)	0.0348 (6)
C3	0.0965 (4)	0.3589 (3)	0.8737 (3)	0.0405 (7)
H3B	0.0509	0.4390	0.8902	0.049*
C4	0.0247 (3)	0.2410 (3)	0.8582 (3)	0.0336 (6)
C5	0.1153 (3)	0.0068 (3)	0.8203 (3)	0.0333 (6)
H5B	0.0572	0.0000	0.8789	0.040*
H5C	0.2167	−0.0227	0.8384	0.040*
C6	0.0360 (3)	−0.0831 (3)	0.6936 (3)	0.0387 (7)
H6B	−0.0012	−0.1667	0.6934	0.046*
H6C	−0.0513	−0.0420	0.6649	0.046*
C7	0.0862 (4)	−0.3532 (3)	0.4587 (4)	0.0547 (9)
H7A	0.0617	−0.4118	0.3734	0.082*
H7B	0.0090	−0.3678	0.4997	0.082*
H7C	0.1850	−0.3704	0.4958	0.082*
C8	0.7433 (4)	0.3470 (4)	0.1814 (4)	0.0540 (9)
H8A	0.8153	0.2796	0.1668	0.081*
H8B	0.7714	0.4106	0.2648	0.081*
H8C	0.7449	0.3912	0.1264	0.081*
C9	0.5861 (3)	0.2846 (3)	0.1602 (3)	0.0346 (6)
C10	0.4009 (3)	0.1407 (3)	0.1252 (3)	0.0391 (7)
H10B	0.3460	0.0609	0.1085	0.047*
C11	0.3377 (3)	0.2588 (3)	0.1412 (3)	0.0317 (6)
C12	0.4499 (3)	0.4921 (3)	0.1791 (3)	0.0317 (6)
H12A	0.3617	0.4992	0.1214	0.038*
H12B	0.5418	0.5208	0.1596	0.038*
C13	0.4371 (3)	0.5828 (3)	0.3059 (3)	0.0362 (7)
H13A	0.4006	0.6665	0.3060	0.043*
H13B	0.3644	0.5427	0.3357	0.043*
C14	0.6070 (4)	0.8524 (3)	0.5396 (3)	0.0522 (9)
H14A	0.6396	0.9112	0.6243	0.078*
H14B	0.5051	0.8703	0.5088	0.078*
H14C	0.6769	0.8662	0.4925	0.078*

	U11	U22	U33	U12	U13	U23
S1	0.0370 (4)	0.0336 (4)	0.0394 (4)	0.0035 (3)	0.0099 (3)	0.0123 (3)
S2	0.0336 (4)	0.0329 (4)	0.0374 (4)	−0.0030 (3)	0.0037 (3)	0.0122 (3)
O1	0.0480 (14)	0.0549 (15)	0.090 (2)	0.0220 (12)	0.0258 (13)	0.0309 (14)
O2	0.0407 (12)	0.0415 (13)	0.0877 (19)	−0.0049 (10)	0.0170 (12)	0.0266 (13)
O3	0.0320 (10)	0.0386 (11)	0.0433 (12)	0.0017 (8)	0.0092 (9)	0.0139 (9)
O4	0.0437 (12)	0.0484 (13)	0.0458 (13)	0.0075 (10)	0.0032 (10)	0.0161 (11)
O5	0.0546 (14)	0.0558 (15)	0.0531 (14)	0.0045 (11)	0.0236 (11)	0.0224 (12)
O6	0.0369 (12)	0.0487 (14)	0.0702 (16)	−0.0152 (10)	0.0100 (11)	0.0215 (12)
O7	0.0376 (12)	0.0411 (13)	0.0683 (16)	0.0083 (9)	0.0096 (10)	0.0207 (11)
O8	0.0283 (10)	0.0365 (11)	0.0409 (12)	−0.0017 (8)	0.0047 (8)	0.0120 (9)
O9	0.0403 (12)	0.0544 (14)	0.0508 (14)	−0.0003 (10)	−0.0048 (10)	0.0227 (11)
O10	0.0472 (13)	0.0512 (14)	0.0444 (13)	−0.0052 (10)	0.0135 (10)	0.0176 (11)
N1	0.0328 (13)	0.0408 (15)	0.0479 (16)	0.0019 (11)	0.0074 (11)	0.0198 (12)
N2	0.0279 (11)	0.0279 (12)	0.0355 (13)	−0.0002 (9)	0.0049 (9)	0.0142 (10)
N3	0.0403 (14)	0.0342 (14)	0.0523 (16)	−0.0069 (11)	0.0075 (12)	0.0176 (12)
N4	0.0332 (13)	0.0364 (14)	0.0360 (14)	−0.0010 (10)	0.0057 (10)	0.0160 (11)
N5	0.0296 (12)	0.0243 (11)	0.0321 (12)	0.0001 (9)	0.0057 (9)	0.0110 (10)
N7	0.0451 (15)	0.0314 (14)	0.0537 (17)	0.0077 (11)	0.0133 (12)	0.0154 (12)
C1	0.0341 (16)	0.056 (2)	0.069 (2)	0.0004 (14)	0.0132 (15)	0.0303 (19)
C2	0.0329 (15)	0.0343 (16)	0.0379 (17)	−0.0080 (12)	0.0025 (12)	0.0170 (13)
C3	0.0459 (17)	0.0277 (15)	0.0475 (19)	0.0011 (12)	0.0069 (14)	0.0156 (14)
C4	0.0315 (14)	0.0328 (15)	0.0365 (16)	0.0010 (11)	0.0078 (12)	0.0132 (13)
C5	0.0347 (15)	0.0281 (14)	0.0389 (16)	−0.0020 (11)	0.0060 (12)	0.0157 (12)
C6	0.0365 (15)	0.0334 (16)	0.0438 (18)	−0.0042 (12)	0.0113 (13)	0.0113 (13)
C7	0.052 (2)	0.0371 (18)	0.081 (3)	0.0074 (15)	0.0218 (18)	0.0253 (18)
C8	0.0326 (17)	0.055 (2)	0.077 (3)	0.0052 (15)	0.0153 (16)	0.0269 (19)
C9	0.0335 (15)	0.0315 (15)	0.0407 (17)	0.0053 (11)	0.0124 (12)	0.0141 (13)
C10	0.0417 (17)	0.0291 (15)	0.0478 (18)	−0.0017 (12)	0.0116 (13)	0.0153 (14)
C11	0.0320 (14)	0.0289 (14)	0.0347 (15)	−0.0008 (11)	0.0066 (11)	0.0129 (12)
C12	0.0327 (14)	0.0253 (13)	0.0386 (16)	−0.0001 (11)	0.0055 (12)	0.0148 (12)
C13	0.0318 (14)	0.0305 (15)	0.0418 (17)	0.0038 (11)	0.0030 (12)	0.0112 (13)
C14	0.0438 (18)	0.0342 (17)	0.076 (3)	−0.0022 (14)	0.0064 (17)	0.0221 (17)

S1—O4	1.420 (2)	C1—H1A	0.9600
S1—O5	1.425 (2)	C1—H1B	0.9600
S1—O3	1.571 (2)	C1—H1C	0.9600
S1—C7	1.749 (3)	C3—C4	1.367 (4)
S2—O9	1.423 (2)	C3—H3B	0.9300
S2—O10	1.424 (2)	C5—C6	1.494 (4)
S2—O8	1.567 (2)	C5—H5B	0.9700
S2—C14	1.746 (3)	C5—H5C	0.9700
O1—N1	1.234 (3)	C6—H6B	0.9700
O2—N1	1.228 (3)	C6—H6C	0.9700
O3—C6	1.461 (3)	C7—H7A	0.9600
O6—N4	1.233 (3)	C7—H7B	0.9600
O7—N4	1.233 (3)	C7—H7C	0.9600
O8—C13	1.464 (3)	C8—C9	1.484 (4)
N1—C4	1.410 (4)	C8—H8A	0.9600
N2—C2	1.363 (3)	C8—H8B	0.9600
N2—C4	1.381 (4)	C8—H8C	0.9600
N2—C5	1.473 (3)	C10—C11	1.366 (4)
N3—C2	1.323 (4)	C10—H10B	0.9300
N3—C3	1.352 (4)	C12—C13	1.490 (4)
N4—C11	1.406 (3)	C12—H12A	0.9700
N5—C9	1.353 (3)	C12—H12B	0.9700
N5—C11	1.383 (3)	C13—H13A	0.9700
N5—C12	1.474 (3)	C13—H13B	0.9700
N7—C9	1.328 (4)	C14—H14A	0.9600
N7—C10	1.354 (4)	C14—H14B	0.9600
C1—C2	1.467 (4)	C14—H14C	0.9600
O4—S1—O5	118.95 (14)	C6—C5—H5C	109.0
O4—S1—O3	109.90 (12)	H5B—C5—H5C	107.8
O5—S1—O3	104.65 (13)	O3—C6—C5	107.7 (2)
O4—S1—C7	109.32 (15)	O3—C6—H6B	110.2
O5—S1—C7	109.50 (15)	C5—C6—H6B	110.2
O3—S1—C7	103.32 (15)	O3—C6—H6C	110.2
O9—S2—O10	118.88 (14)	C5—C6—H6C	110.2
O9—S2—O8	104.78 (13)	H6B—C6—H6C	108.5
O10—S2—O8	109.83 (12)	S1—C7—H7A	109.5
O9—S2—C14	109.74 (15)	S1—C7—H7B	109.5
O10—S2—C14	109.15 (15)	H7A—C7—H7B	109.5
O8—S2—C14	103.28 (15)	S1—C7—H7C	109.5
C6—O3—S1	118.58 (18)	H7A—C7—H7C	109.5
C13—O8—S2	118.53 (17)	H7B—C7—H7C	109.5
O2—N1—O1	123.1 (3)	C9—C8—H8A	109.5
O2—N1—C4	119.8 (2)	C9—C8—H8B	109.5
O1—N1—C4	117.1 (3)	H8A—C8—H8B	109.5
C2—N2—C4	104.9 (2)	C9—C8—H8C	109.5
C2—N2—C5	125.9 (2)	H8A—C8—H8C	109.5
C4—N2—C5	129.1 (2)	H8B—C8—H8C	109.5
C2—N3—C3	106.4 (2)	N7—C9—N5	112.3 (2)
O7—N4—O6	122.9 (2)	N7—C9—C8	124.0 (3)
O7—N4—C11	119.9 (2)	N5—C9—C8	123.7 (3)
O6—N4—C11	117.3 (2)	N7—C10—C11	109.8 (3)
C9—N5—C11	105.3 (2)	N7—C10—H10B	125.1
C9—N5—C12	126.1 (2)	C11—C10—H10B	125.1
C11—N5—C12	128.5 (2)	C10—C11—N5	106.9 (2)
C9—N7—C10	105.7 (2)	C10—C11—N4	127.9 (3)
C2—C1—H1A	109.5	N5—C11—N4	125.1 (2)
C2—C1—H1B	109.5	N5—C12—C13	113.3 (2)
H1A—C1—H1B	109.5	N5—C12—H12A	108.9
C2—C1—H1C	109.5	C13—C12—H12A	108.9
H1A—C1—H1C	109.5	N5—C12—H12B	108.9
H1B—C1—H1C	109.5	C13—C12—H12B	108.9
N3—C2—N2	112.0 (3)	H12A—C12—H12B	107.7
N3—C2—C1	124.5 (3)	O8—C13—C12	108.1 (2)
N2—C2—C1	123.6 (3)	O8—C13—H13A	110.1
N3—C3—C4	109.2 (3)	C12—C13—H13A	110.1
N3—C3—H3B	125.4	O8—C13—H13B	110.1
C4—C3—H3B	125.4	C12—C13—H13B	110.1
C3—C4—N2	107.5 (2)	H13A—C13—H13B	108.4
C3—C4—N1	127.4 (3)	S2—C14—H14A	109.5
N2—C4—N1	125.1 (2)	S2—C14—H14B	109.5
N2—C5—C6	113.0 (2)	H14A—C14—H14B	109.5
N2—C5—H5B	109.0	S2—C14—H14C	109.5
C6—C5—H5B	109.0	H14A—C14—H14C	109.5
N2—C5—H5C	109.0	H14B—C14—H14C	109.5
O4—S1—O3—C6	36.6 (2)	C4—N2—C5—C6	80.8 (3)
O5—S1—O3—C6	165.4 (2)	S1—O3—C6—C5	−174.80 (18)
C7—S1—O3—C6	−79.9 (2)	N2—C5—C6—O3	77.7 (3)
O9—S2—O8—C13	165.3 (2)	C10—N7—C9—N5	−0.1 (3)
O10—S2—O8—C13	36.5 (2)	C10—N7—C9—C8	179.2 (3)
C14—S2—O8—C13	−79.8 (2)	C11—N5—C9—N7	0.4 (3)
C3—N3—C2—N2	−0.8 (3)	C12—N5—C9—N7	−176.3 (3)
C3—N3—C2—C1	179.1 (3)	C11—N5—C9—C8	−179.0 (3)
C4—N2—C2—N3	1.0 (3)	C12—N5—C9—C8	4.4 (5)
C5—N2—C2—N3	−176.3 (3)	C9—N7—C10—C11	−0.2 (3)
C4—N2—C2—C1	−178.8 (3)	N7—C10—C11—N5	0.4 (3)
C5—N2—C2—C1	3.9 (4)	N7—C10—C11—N4	−177.2 (3)
C2—N3—C3—C4	0.2 (3)	C9—N5—C11—C10	−0.5 (3)
N3—C3—C4—N2	0.4 (3)	C12—N5—C11—C10	176.1 (3)
N3—C3—C4—N1	−179.7 (3)	C9—N5—C11—N4	177.3 (3)
C2—N2—C4—C3	−0.9 (3)	C12—N5—C11—N4	−6.1 (4)
C5—N2—C4—C3	176.3 (3)	O7—N4—C11—C10	172.6 (3)
C2—N2—C4—N1	179.3 (3)	O6—N4—C11—C10	−7.8 (4)
C5—N2—C4—N1	−3.5 (5)	O7—N4—C11—N5	−4.7 (4)
O2—N1—C4—C3	175.3 (3)	O6—N4—C11—N5	174.9 (3)
O1—N1—C4—C3	−4.2 (5)	C9—N5—C12—C13	−102.3 (3)
O2—N1—C4—N2	−4.9 (4)	C11—N5—C12—C13	81.8 (3)
O1—N1—C4—N2	175.7 (3)	S2—O8—C13—C12	−174.36 (17)
C2—N2—C5—C6	−102.5 (3)	N5—C12—C13—O8	77.5 (3)

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···O10iv	0.96	2.52	3.423 (4)	157
C12—H12A···O1v	0.97	2.50	3.250 (5)	134
C12—H12B···N3vi	0.97	2.53	3.472 (4)	164
C14—H14B···O5vii	0.96	2.59	3.507 (4)	160
C14—H14C···O4viii	0.96	2.55	3.414 (4)	150

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⋯O10iv	0.96	2.52	3.423 (4)	157
C12—H12A⋯O1v	0.97	2.50	3.250 (5)	134
C12—H12B⋯N3vi	0.97	2.53	3.472 (4)	164
C14—H14B⋯O5vii	0.96	2.59	3.507 (4)	160
C14—H14C⋯O4viii	0.96	2.55	3.414 (4)	150

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