1-Hydroxy-ethyl-2-methyl-5-nitro-imidazolium 3-carb-oxy-4-hydroxy-benzene-sulfonate.

Cocrystallization of 1-hydroxy-ethyl-2-methyl-5-nitroimidazole (metronidazole) and 5-sulfosalicylic acid (5-H(2)SSA) from methanol solution yields the title salt, C(6)H(10)N(3)O(3) (+)·C(7)H(5)O(6)S(-). In the crystal structure, the ions are linked by a combination of inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional framework. The hydroxyl group of the cation is disordered over two sites in a 0.860 (4):0.140 (4) ratio.

Related literature

For related literature, see: Athar et al. (2005 ▶); Bharti et al. (2002 ▶); Castelli et al. (2000 ▶); Cohen-Jonathan et al. (2001 ▶); Crozet et al. (2002 ▶); Galván-Tejada et al. (2002 ▶); Hodgkiss (1998 ▶); Kennedy et al. (2006 ▶); Meng et al. (2007 ▶); Skupin et al. (1997 ▶); Wu et al. (2003 ▶).

Experimental

Crystal data

C6H10N3O3 +·C7H5O6S−

M = 389.34

Monoclinic,

a = 8.8438 (3) Å

b = 13.0249 (4) Å

c = 14.148 (5) Å

β = 100.413 (1)°

V = 1602.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 294 (2) K

0.35 × 0.26 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.904, T max = 0.950

17399 measured reflections

3503 independent reflections

3156 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.06

3503 reflections

262 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018643/lh2643sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018643/lh2643Isup2.hkl

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

C6H10N3O3+·C7H5O6S–	F000 = 808
Mr = 389.34	Dx = 1.613 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9747 reflections
a = 8.8438 (3) Å	θ = 2.5–28.2º
b = 13.0249 (4) Å	µ = 0.26 mm−1
c = 14.148 (5) Å	T = 294 (2) K
β = 100.4130 (10)º	Block, colorless
V = 1602.9 (6) Å3	0.35 × 0.26 × 0.20 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3503 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	3156 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 294(2) K	θmax = 27.0º
0.3° wide ω exposures scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)	h = −11→11
Tmin = 0.905, Tmax = 0.950	k = −16→16
17399 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0695P)2 + 0.4716P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3503 reflections	Δρmax = 0.32 e Å−3
262 parameters	Δρmin = −0.30 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
C1	0.26714 (18)	0.68882 (13)	0.68052 (11)	0.0389 (3)
C2	0.3234 (2)	0.78986 (13)	0.68903 (12)	0.0441 (4)
C3	0.4814 (2)	0.80629 (14)	0.69525 (14)	0.0520 (4)
H3	0.5198	0.8729	0.7007	0.062*
C4	0.5807 (2)	0.72533 (14)	0.69348 (13)	0.0462 (4)
H4	0.6851	0.7376	0.6965	0.055*
C5	0.52498 (18)	0.62468 (13)	0.68713 (11)	0.0380 (3)
C6	0.36914 (18)	0.60747 (13)	0.68103 (11)	0.0380 (3)
H6	0.3320	0.5405	0.6772	0.046*
C7	0.1012 (2)	0.67003 (14)	0.67435 (13)	0.0433 (4)
C8	0.1649 (2)	0.27776 (14)	0.56001 (12)	0.0443 (4)
C9	0.2283 (2)	0.36913 (14)	0.54592 (13)	0.0474 (4)
H9	0.1782	0.4318	0.5342	0.057*
C10	0.41167 (19)	0.25196 (13)	0.56990 (11)	0.0405 (4)
C11	0.5662 (2)	0.20700 (17)	0.58081 (16)	0.0591 (5)
H11A	0.6376	0.2584	0.5680	0.089*
H11B	0.5650	0.1512	0.5363	0.089*
H11C	0.5969	0.1820	0.6452	0.089*
C12	0.2655 (3)	0.09157 (14)	0.58498 (13)	0.0546 (5)
H12A	0.1935	0.0764	0.6273	0.065*
H12B	0.3647	0.0633	0.6137	0.065*
C13	0.2110 (3)	0.04186 (16)	0.48829 (16)	0.0625 (6)
H13A	0.2000	−0.0315	0.4965	0.075*	0.860 (4)
H13B	0.1113	0.0694	0.4597	0.075*	0.860 (4)
H13C	0.2960	0.0404	0.4535	0.075*	0.140 (4)
H13D	0.1834	−0.0288	0.4987	0.075*	0.140 (4)
N1	0.27916 (17)	0.20437 (10)	0.57531 (10)	0.0415 (3)
N2	0.38028 (18)	0.35061 (12)	0.55237 (11)	0.0441 (3)
H2	0.447 (3)	0.3933 (19)	0.5509 (15)	0.055 (6)*
N3	0.0052 (2)	0.26065 (16)	0.56153 (12)	0.0582 (4)
O1	0.06220 (15)	0.57238 (10)	0.66817 (11)	0.0551 (4)
H1	−0.029 (3)	0.567 (2)	0.6806 (19)	0.083*
O2	0.00803 (16)	0.73868 (11)	0.67490 (13)	0.0644 (4)
O3	0.23266 (19)	0.87220 (10)	0.69337 (12)	0.0612 (4)
H3A	0.144 (4)	0.849 (3)	0.688 (2)	0.092*
O4	0.80111 (14)	0.55223 (12)	0.72322 (11)	0.0577 (4)
O5	0.59335 (15)	0.44064 (11)	0.74685 (10)	0.0552 (4)
O6	0.62653 (14)	0.48356 (9)	0.58626 (9)	0.0447 (3)
O7	−0.0358 (2)	0.17473 (15)	0.58045 (15)	0.0874 (6)
O8	−0.0796 (2)	0.33520 (18)	0.54514 (15)	0.0865 (6)
O9	0.3138 (2)	0.06004 (17)	0.42931 (13)	0.0725 (7)	0.860 (4)
H9A	0.260 (4)	0.065 (3)	0.3759 (14)	0.109*	0.860 (4)
O9'	0.1003 (12)	0.0853 (9)	0.4339 (7)	0.066 (4)	0.140 (4)
H9'	0.13 (3)	0.135 (12)	0.408 (15)	0.099*	0.140 (4)
S1	0.64580 (4)	0.51687 (3)	0.68609 (3)	0.03782 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0401 (8)	0.0393 (8)	0.0371 (8)	−0.0030 (7)	0.0064 (6)	−0.0011 (6)
C2	0.0514 (10)	0.0369 (8)	0.0437 (9)	−0.0007 (7)	0.0078 (7)	0.0033 (7)
C3	0.0565 (11)	0.0377 (9)	0.0610 (11)	−0.0127 (8)	0.0084 (9)	0.0039 (8)
C4	0.0425 (9)	0.0445 (9)	0.0514 (10)	−0.0126 (7)	0.0077 (7)	0.0038 (7)
C5	0.0367 (8)	0.0395 (8)	0.0381 (8)	−0.0048 (6)	0.0070 (6)	0.0012 (6)
C6	0.0380 (8)	0.0358 (8)	0.0404 (8)	−0.0065 (6)	0.0075 (6)	−0.0027 (6)
C7	0.0412 (8)	0.0417 (9)	0.0472 (9)	0.0003 (7)	0.0088 (7)	−0.0034 (7)
C8	0.0451 (9)	0.0486 (10)	0.0391 (8)	−0.0103 (7)	0.0073 (7)	−0.0059 (7)
C9	0.0491 (9)	0.0401 (9)	0.0517 (10)	−0.0048 (7)	0.0058 (8)	−0.0027 (7)
C10	0.0464 (9)	0.0394 (8)	0.0343 (8)	−0.0087 (7)	0.0036 (6)	−0.0016 (6)
C11	0.0510 (10)	0.0617 (12)	0.0620 (12)	0.0035 (9)	0.0035 (9)	0.0017 (10)
C12	0.0836 (14)	0.0359 (9)	0.0447 (9)	−0.0151 (9)	0.0128 (9)	0.0021 (7)
C13	0.0888 (16)	0.0447 (10)	0.0561 (12)	−0.0255 (11)	0.0188 (11)	−0.0107 (9)
N1	0.0520 (8)	0.0365 (7)	0.0351 (7)	−0.0120 (6)	0.0060 (6)	−0.0017 (5)
N2	0.0465 (8)	0.0371 (7)	0.0480 (8)	−0.0133 (6)	0.0066 (6)	−0.0014 (6)
N3	0.0501 (9)	0.0760 (12)	0.0500 (9)	−0.0176 (9)	0.0134 (7)	−0.0135 (8)
O1	0.0359 (6)	0.0428 (7)	0.0875 (10)	−0.0024 (5)	0.0135 (6)	−0.0028 (6)
O2	0.0482 (7)	0.0479 (8)	0.0985 (12)	0.0063 (6)	0.0172 (7)	−0.0104 (7)
O3	0.0614 (8)	0.0360 (7)	0.0852 (11)	0.0023 (6)	0.0104 (8)	0.0021 (7)
O4	0.0333 (6)	0.0637 (9)	0.0728 (9)	−0.0072 (6)	0.0014 (6)	−0.0126 (7)
O5	0.0534 (7)	0.0544 (8)	0.0578 (8)	0.0007 (6)	0.0105 (6)	0.0214 (6)
O6	0.0486 (7)	0.0396 (6)	0.0456 (7)	−0.0045 (5)	0.0079 (5)	−0.0006 (5)
O7	0.0759 (11)	0.0821 (12)	0.1140 (15)	−0.0409 (10)	0.0429 (10)	−0.0266 (11)
O8	0.0517 (9)	0.1110 (16)	0.0978 (13)	0.0069 (10)	0.0161 (9)	0.0071 (11)
O9	0.0805 (13)	0.0892 (14)	0.0503 (10)	−0.0317 (11)	0.0186 (9)	−0.0189 (9)
O9'	0.082 (8)	0.066 (7)	0.047 (6)	0.001 (6)	0.006 (5)	−0.013 (5)
S1	0.0307 (2)	0.0400 (2)	0.0417 (2)	−0.00536 (14)	0.00351 (15)	0.00333 (15)

C1—C6	1.391 (2)	C11—H11B	0.9600
C1—C2	1.405 (2)	C11—H11C	0.9600
C1—C7	1.475 (2)	C12—N1	1.482 (2)
C2—O3	1.348 (2)	C12—C13	1.512 (3)
C2—C3	1.400 (3)	C12—H12A	0.9700
C3—C4	1.376 (3)	C12—H12B	0.9700
C3—H3	0.9300	C13—O9'	1.265 (8)
C4—C5	1.398 (2)	C13—O9	1.361 (3)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.384 (2)	C13—H13B	0.9700
C5—S1	1.7662 (17)	C13—H13C	0.9700
C6—H6	0.9300	C13—H13D	0.9700
C7—O2	1.217 (2)	N2—H2	0.81 (2)
C7—O1	1.317 (2)	N3—O7	1.221 (3)
C8—C9	1.346 (2)	N3—O8	1.223 (3)
C8—N1	1.379 (2)	O1—H1	0.86 (3)
C8—N3	1.434 (2)	O3—H3A	0.83 (3)
C9—N2	1.352 (2)	O4—S1	1.4539 (12)
C9—H9	0.9300	O5—S1	1.4437 (13)
C10—N2	1.328 (2)	O6—S1	1.4579 (14)
C10—N1	1.340 (2)	O9—H13C	0.4764
C10—C11	1.469 (3)	O9—H9A	0.82 (1)
C11—H11A	0.9600	O9'—H9'	0.82 (1)
C6—C1—C2	119.60 (15)	C13—C12—H12B	109.4
C6—C1—C7	120.76 (15)	H12A—C12—H12B	108.0
C2—C1—C7	119.61 (15)	O9'—C13—O9	94.5 (6)
O3—C2—C3	118.11 (16)	O9'—C13—C12	116.4 (5)
O3—C2—C1	123.01 (16)	O9—C13—C12	109.93 (18)
C3—C2—C1	118.87 (16)	O9'—C13—H13A	115.5
C4—C3—C2	120.97 (16)	O9—C13—H13A	109.7
C4—C3—H3	119.5	C12—C13—H13A	109.7
C2—C3—H3	119.5	O9—C13—H13B	109.7
C3—C4—C5	120.09 (16)	C12—C13—H13B	109.7
C3—C4—H4	120.0	H13A—C13—H13B	108.2
C5—C4—H4	120.0	O9'—C13—H13C	106.6
C6—C5—C4	119.46 (16)	C12—C13—H13C	108.5
C6—C5—S1	117.90 (12)	H13A—C13—H13C	98.3
C4—C5—S1	122.63 (13)	H13B—C13—H13C	121.6
C5—C6—C1	120.98 (15)	O9'—C13—H13D	109.2
C5—C6—H6	119.5	O9—C13—H13D	118.2
C1—C6—H6	119.5	C12—C13—H13D	108.4
O2—C7—O1	122.75 (17)	H13B—C13—H13D	100.4
O2—C7—C1	123.05 (17)	H13C—C13—H13D	107.4
O1—C7—C1	114.20 (15)	C10—N1—C8	107.09 (14)
C9—C8—N1	108.85 (15)	C10—N1—C12	123.38 (16)
C9—C8—N3	125.28 (18)	C8—N1—C12	129.19 (16)
N1—C8—N3	125.85 (17)	C10—N2—C9	110.91 (15)
C8—C9—N2	105.54 (16)	C10—N2—H2	122.7 (16)
C8—C9—H9	127.2	C9—N2—H2	126.1 (16)
N2—C9—H9	127.2	O7—N3—O8	124.99 (19)
N2—C10—N1	107.62 (16)	O7—N3—C8	118.5 (2)
N2—C10—C11	124.35 (17)	O8—N3—C8	116.46 (19)
N1—C10—C11	128.03 (17)	C7—O1—H1	108 (2)
C10—C11—H11A	109.5	C2—O3—H3A	105 (2)
C10—C11—H11B	109.5	C13—O9—H9A	104 (3)
H11A—C11—H11B	109.5	H13C—O9—H9A	119.2
C10—C11—H11C	109.5	C13—O9'—H9'	109 (10)
H11A—C11—H11C	109.5	O5—S1—O4	112.76 (9)
H11B—C11—H11C	109.5	O5—S1—O6	112.23 (8)
N1—C12—C13	111.03 (16)	O4—S1—O6	112.44 (8)
N1—C12—H12A	109.4	O5—S1—C5	106.37 (8)
C13—C12—H12A	109.4	O4—S1—C5	106.18 (8)
N1—C12—H12B	109.4	O6—S1—C5	106.24 (7)
C6—C1—C2—O3	−176.99 (16)	C11—C10—N1—C8	−179.79 (17)
C7—C1—C2—O3	1.0 (3)	N2—C10—N1—C12	174.03 (15)
C6—C1—C2—C3	1.7 (2)	C11—C10—N1—C12	−6.0 (3)
C7—C1—C2—C3	179.71 (16)	C9—C8—N1—C10	−0.29 (19)
O3—C2—C3—C4	178.52 (17)	N3—C8—N1—C10	−178.63 (16)
C1—C2—C3—C4	−0.2 (3)	C9—C8—N1—C12	−173.61 (17)
C2—C3—C4—C5	−1.2 (3)	N3—C8—N1—C12	8.0 (3)
C3—C4—C5—C6	1.1 (3)	C13—C12—N1—C10	−96.5 (2)
C3—C4—C5—S1	−179.15 (14)	C13—C12—N1—C8	75.8 (2)
C4—C5—C6—C1	0.4 (2)	N1—C10—N2—C9	−0.10 (19)
S1—C5—C6—C1	−179.38 (12)	C11—C10—N2—C9	179.92 (17)
C2—C1—C6—C5	−1.8 (2)	C8—C9—N2—C10	−0.1 (2)
C7—C1—C6—C5	−179.78 (15)	C9—C8—N3—O7	−175.94 (19)
C6—C1—C7—O2	179.04 (18)	N1—C8—N3—O7	2.1 (3)
C2—C1—C7—O2	1.1 (3)	C9—C8—N3—O8	2.8 (3)
C6—C1—C7—O1	−1.0 (2)	N1—C8—N3—O8	−179.15 (17)
C2—C1—C7—O1	−178.93 (16)	C6—C5—S1—O5	−42.03 (15)
N1—C8—C9—N2	0.23 (19)	C4—C5—S1—O5	138.20 (15)
N3—C8—C9—N2	178.58 (16)	C6—C5—S1—O4	−162.37 (13)
N1—C12—C13—O9'	−44.9 (7)	C4—C5—S1—O4	17.86 (17)
N1—C12—C13—O9	61.0 (3)	C6—C5—S1—O6	77.73 (14)
N2—C10—N1—C8	0.23 (18)	C4—C5—S1—O6	−102.04 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.83 (3)	1.86 (3)	2.618 (2)	151 (3)
N2—H2···O6	0.81 (2)	1.97 (2)	2.7557 (19)	163 (2)
C13—H13D···O7i	0.97	2.46	3.280 (3)	142
C11—H11C···O4ii	0.96	2.55	3.457 (3)	157
O9—H9A···O5iii	0.82 (1)	2.129 (13)	2.940 (2)	170 (4)
O9'—H9'···O2iv	0.82 (1)	2.258 (13)	2.830 (2)	127 (2)
O1—H1···O4v	0.86 (3)	1.73 (3)	2.5801 (19)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.83 (3)	1.86 (3)	2.618 (2)	151 (3)
N2—H2⋯O6	0.81 (2)	1.97 (2)	2.7557 (19)	163 (2)
C13—H13D⋯O7i	0.97	2.46	3.280 (3)	142
C11—H11C⋯O4ii	0.96	2.55	3.457 (3)	157
O9—H9A⋯O5iii	0.82 (1)	2.129 (13)	2.940 (2)	170 (4)
O9′—H9′⋯O2iv	0.82 (1)	2.258 (13)	2.830 (2)	127 (2)
O1—H1⋯O4v	0.86 (3)	1.73 (3)	2.5801 (19)	171 (3)

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