1-Hydroxy­ethyl-2-methyl-5-nitro­imidazolium 3-carb­oxy-4-hydroxy­benzene­sulfonate

Yang, B.

doi:10.1107/S1600536808018643

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages o1338-o1339

doi:10.1107/S1600536808018643

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1-Hydroxyethyl-2-methyl-5-nitroimidazolium 3-carboxy-4-hydroxybenzenesulfonate

Bo Yang ^a ^*

^aWuhan Grand Pharmaceutical Group Co. Ltd, No. 5 Gu Tian Road, Wuhan 430035, People's Republic of China
^*Correspondence e-mail: b_yang58@126.com

(Received 15 June 2008; accepted 20 June 2008; online 25 June 2008)

Cocrystallization of 1-hydroxyethyl-2-methyl-5-nitroimidazole (metronidazole) and 5-sulfosalicylic acid (5-H₂SSA) from methanol solution yields the title salt, C₆H₁₀N₃O₃⁺·C₇H₅O₆S⁻. In the crystal structure, the ions are linked by a combination of intermolecular 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_r = 389.34
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.06
3503 reflections
262 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.30 e Å⁻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′⋯O2^iv	0.82 (1)	2.258 (13)	2.830 (2)	127 (2)
O1—H1⋯O4^v	0.86 (3)	1.73 (3)	2.5801 (19)	171 (3)
Symmetry codes: (i) -x, -y, -z+1; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z+1; (v) x-1, y, z.

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.

Supporting information

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

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

checkCIF report

Comment top

1-Hydroxyethyl-2-methyl-5-nitrimidazole (metronidazole) is often used in the treatment of anaerobic protozoan and bacterial infections (Castelli et al., 2000; Cohen-Jonathan et al., 2001; Hodgkiss et al., 1998). However, the low solubility in water makes its absorption in human body much less than expected. Recently, many efforts have been devoted to developing some new substitutes for the medicine, i.e. i) metal-organic coordination compounds (Kennedy et al., 2006; Galván-Tejada et al., 2002; Athar et al., 2005; Bharti et al., 2002; Wu et al., 2003), ii) organic substitute derivatives (Crozet et al., 2002, Skupin et al., 1997) and iii) pharmaceutical co-crystals. In this paper, we report the 1:1 molecular adduct formed by metronidazole 5-sulfosalicylic acid (5-H₂SSA), (I).

In (I), the H atom is transferred from the sulfonic acid group to the imidazole N atom (Fig.1) forming an 1:1 organic adduct, which is similar to the analogous organic adducts reported (Meng et al., 2007). The hydroxyl O atom is disordered at two sites with occupancy being 0.86 (1)/0.14 (1) for the major and minor components, respectively.

In the crystal packing, the component ions are linked by a combination of O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1), forming a three-dimensional network (Fig.2). There are no other interactions (e.g. C—H···π and π-π) observed in the crystal structure by using PLATON (Spek, 2003).

Related literature top

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 top

All the reagents and solvents were used as obtained without further purification. Equivalent molar amount of metronidazole and 5-sulfosalicylic acid dihydrate were dissolved in methanol (10 ml). The mixture was stirred for ten minutes at 300 K and then filtered. Block colorless crystals of (I) suitable for single-crystal X-ray diffraction analysis were grown by slow evaporation of the solution at the bottom of the vessel in two days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Spek, 2003).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H-bonds are shown in dashed lines.
	Fig. 2. Part of the crystal structure of (I), showing the formation of the three-dimensional framework structure. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in the motif have been omitted from the drawing.

1-Hydroxyethyl-2-methyl-5-nitroimidazolium 3-carboxy-4-hydroxybenzenesulfonate top

Crystal data top

C₆H₁₀N₃O₃⁺·C₇H₅O₆S⁻	F(000) = 808
M_r = 389.34	D_x = 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 = 2.5–28.2°
b = 13.0249 (4) Å	µ = 0.26 mm⁻¹
c = 14.148 (5) Å	T = 294 K
β = 100.413 (1)°	Block, colorless
V = 1602.9 (6) Å³	0.35 × 0.26 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3503 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	3156 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
0.3° wide ω exposures scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −11→11
T_min = 0.905, T_max = 0.950	k = −16→16
17399 measured reflections	l = −18→18

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0695P)² + 0.4716P] where P = (F_o² + 2F_c²)/3
3503 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.32 e Å⁻³
4 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₆H₁₀N₃O₃⁺·C₇H₅O₆S⁻	V = 1602.9 (6) Å³
M_r = 389.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.8438 (3) Å	µ = 0.26 mm⁻¹
b = 13.0249 (4) Å	T = 294 K
c = 14.148 (5) Å	0.35 × 0.26 × 0.20 mm
β = 100.413 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3503 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3156 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.950	R_int = 0.020
17399 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	4 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.32 e Å⁻³
3503 reflections	Δρ_min = −0.31 e Å⁻³
262 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)	2.13 (1)	2.940 (2)	170 (4)
O9′—H9′···O2^iv	0.82 (1)	2.26 (1)	2.830 (2)	127 (2)
O1—H1···O4^v	0.86 (3)	1.73 (3)	2.5801 (19)	171 (3)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x, −y+1, −z+1; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₆H₁₀N₃O₃⁺·C₇H₅O₆S⁻
M_r	389.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	8.8438 (3), 13.0249 (4), 14.148 (5)
β (°)	100.413 (1)
V (Å³)	1602.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.35 × 0.26 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.905, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	17399, 3503, 3156
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.118, 1.07
No. of reflections	3503
No. of parameters	262
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.31

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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)	142.3
C11—H11C···O4ⁱⁱ	0.96	2.55	3.457 (3)	156.7
O9—H9A···O5ⁱⁱⁱ	0.82 (1)	2.129 (13)	2.940 (2)	170 (4)
O9'—H9'···O2^iv	0.82 (1)	2.258 (13)	2.830 (2)	127 (2)
O1—H1···O4^v	0.86 (3)	1.73 (3)	2.5801 (19)	171 (3)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x, −y+1, −z+1; (v) x−1, y, z.

Acknowledgements

This work was supported by Wuhan Grand Pharmaceutical Group Co. Ltd.

References

Athar, F., Husain, K., Abid, M., Agarwal, S. M., Coles, S. J., Hursthouse, M. B., Maurya, M. R. & Azam, A. (2005). Chem. Biodivers. 2, 1220–1330. Web of Science CSD CrossRef Google Scholar
Bharti, N., Shailendra, Coles, S. J., Hursthouse, M. B., Mayer, T. A., Gonzalez Garza, M. T., Cruz-Vega, D. E., Mata-Cardenas, B. D., Naqvi, F., Maurya, M. R. & Azam, A. (2002). Helv. Chim. Acta, 85, 2704–2712. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Castelli, M., Malagoli, M., Lupo, L., Bofia, S., Paolucci, F., Cermelli, C., Zanca, A. & Baggio, G. (2000). J. Antimicrob. Chemother. 46, 541–550. Web of Science CrossRef PubMed CAS Google Scholar
Cohen-Jonathan, E., Evans, S. M., Koch, C. J., Muschel, R. J., McKenna, W. J., Wu, J. & Bernhard, E. J. (2001). Cancer Res. 161, 2289–2293. Google Scholar
Crozet, M. D., Vanelle, P., Giorgi, M. & Gellis, A. (2002). Acta Cryst. C58, o496–o498. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Galván-Tejada, N., Bernès, S., Castillo-Blum, S. E., Nöth, H., Vicente, R. & Barba-Behrens, N. (2002). J. Inorg. Biochem. 91, 339–348. Web of Science CSD CrossRef PubMed CAS Google Scholar
Hodgkiss, R. J. (1998). Anti-Cancer Drug Des. 13, 687–702. Web of Science CAS PubMed Google Scholar
Kennedy, D. C., Wu, A., Patrick, B. O. & James, B. R. (2006). J. Inorg. Biochem. 100, 1974–1982. Web of Science CSD CrossRef PubMed CAS Google Scholar
Meng, X.-G., Zhou, C.-S., Wang, L. & Liu, C.-L. (2007). Acta Cryst. C63, o667–o670. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Skupin, S., Cooper, T. G., Frohlich, R., Prigge, J. & Haufe, G. (1997). Tetrahedron Asymm. 8, 2453–2464. CSD CrossRef CAS Web of Science Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, A., Kennedy, D. C., Patrick, B. O. & James, B. R. (2003). Inorg. Chem. 42, 7579–7586. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 64| Part 7| July 2008| Pages o1338-o1339

doi:10.1107/S1600536808018643

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-Hy­droxy­ethyl-2-methyl-5-nitro­imidazolium 3-carb­­oxy-4-hy­droxy­benzene­sulfonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-Hydroxyethyl-2-methyl-5-nitroimidazolium 3-carboxy-4-hydroxybenzenesulfonate