1,3-Bis(carboxy-meth-yl)imidazolium triiodide 1-carboxyl-atomethyl-3-carboxy-methyl-imidazolium.

In the title compound, C(7)H(9)N(2)O(4) (+)·I(3) (-)·C(7)H(8)N(2)O(4), the two imidazolium units are hydrogen bonded through the carboxyl groups. The units are further linked via inter-molecular O-H⋯O hydrogen bonding, resulting in a one-dimensional ladder-type structure. As a result, the two carb-oxy groups of each imidazolium unit adopt a cis configuration with respect to the imidazolium ring.

Related literature

For the preparation of 1,3-bis­(carboxy­meth­yl)imidazole, see: Kratochvíl et al. (1988 ▶); Fei et al. (2004 ▶); Barczynski et al. (2008 ▶). For its structure, see: Kratochvíl et al. (1988 ▶).

Experimental

Crystal data

C7H9N2O4 +·I3 −·C7H8N2O4

M = 750.02

Monoclinic,

a = 22.260 (3) Å

b = 10.1973 (17) Å

c = 10.1077 (17) Å

β = 92.209 (2)°

V = 2292.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 4.14 mm−1

T = 298 K

0.49 × 0.44 × 0.40 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.237, T max = 0.289 (expected range = 0.157–0.191)

6257 measured reflections

2248 independent reflections

1702 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.112

S = 1.03

2248 reflections

140 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.84 e Å−3

Δρmin = −0.99 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025239/bt2982sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025239/bt2982Isup2.hkl

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

C7H9N2O4+·I3−·C7H8N2O4	F(000) = 1408
Mr = 750.02	Dx = 2.173 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.260 (3) Å	Cell parameters from 2974 reflections
b = 10.1973 (17) Å	θ = 3.0–27.2°
c = 10.1077 (17) Å	µ = 4.14 mm−1
β = 92.209 (2)°	T = 298 K
V = 2292.7 (6) Å3	Plate, red
Z = 4	0.49 × 0.44 × 0.40 mm

Bruker SMART 1000 CCD area-detector diffractometer	2248 independent reflections
Radiation source: fine-focus sealed tube	1702 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→27
Tmin = 0.237, Tmax = 0.289	k = −11→12
6257 measured reflections	l = −9→12

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0655P)2 + 3.4411P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2248 reflections	Δρmax = 0.84 e Å−3
140 parameters	Δρmin = −0.98 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (2)

	x	y	z	Uiso*/Ueq
O1	0.46232 (19)	−0.1010 (4)	0.1047 (4)	0.0471 (10)
O2	0.45813 (18)	0.1069 (4)	0.1678 (4)	0.0467 (10)
O3	0.4311 (2)	0.7258 (4)	−0.0724 (5)	0.0608 (13)
O4	0.4461 (2)	0.5756 (4)	0.0836 (4)	0.0533 (11)
N1	0.38543 (17)	0.1836 (4)	−0.0301 (4)	0.0331 (9)
N2	0.38902 (19)	0.3887 (4)	−0.0756 (4)	0.0337 (9)
C1	0.4130 (2)	0.2736 (5)	−0.0999 (5)	0.0349 (11)
H1	0.4441	0.2581	−0.1566	0.042*
C2	0.3446 (2)	0.3728 (5)	0.0145 (6)	0.0415 (12)
H2	0.3207	0.4385	0.0487	0.050*
C3	0.3423 (3)	0.2448 (5)	0.0434 (6)	0.0431 (13)
H3	0.3167	0.2047	0.1016	0.052*
C4	0.4439 (2)	0.0124 (5)	0.0929 (5)	0.0357 (11)
C5	0.4008 (2)	0.0437 (5)	−0.0226 (5)	0.0362 (11)
H5A	0.4189	0.0175	−0.1043	0.043*
H5B	0.3643	−0.0069	−0.0140	0.043*
C6	0.4295 (2)	0.6072 (5)	−0.0261 (5)	0.0365 (11)
C7	0.4056 (3)	0.5151 (5)	−0.1311 (5)	0.0381 (12)
H7A	0.3706	0.5541	−0.1757	0.046*
H7B	0.4359	0.5019	−0.1962	0.046*
I1	0.228024 (19)	0.42974 (5)	0.27861 (4)	0.0609 (2)
I2	0.2500	0.2500	0.5000	0.0519 (2)
H2O	0.5000	0.106 (9)	0.2500	0.08 (3)*
H3O	0.435 (4)	0.780 (7)	−0.014 (9)	0.07 (2)*

	U11	U22	U33	U12	U13	U23
O1	0.054 (2)	0.037 (2)	0.049 (2)	0.0015 (17)	−0.0163 (19)	−0.0009 (17)
O2	0.052 (2)	0.044 (2)	0.042 (2)	0.0067 (17)	−0.0205 (18)	−0.0129 (17)
O3	0.094 (4)	0.038 (2)	0.048 (3)	−0.016 (2)	−0.026 (2)	0.009 (2)
O4	0.078 (3)	0.051 (2)	0.030 (2)	−0.0123 (19)	−0.014 (2)	0.0074 (17)
N1	0.030 (2)	0.035 (2)	0.034 (2)	0.0008 (17)	−0.0065 (17)	−0.0041 (18)
N2	0.038 (2)	0.040 (2)	0.023 (2)	−0.0028 (18)	−0.0028 (17)	−0.0004 (17)
C1	0.034 (3)	0.040 (3)	0.031 (3)	0.002 (2)	0.001 (2)	−0.005 (2)
C2	0.036 (3)	0.046 (3)	0.043 (3)	0.003 (2)	0.010 (2)	0.000 (2)
C3	0.038 (3)	0.049 (3)	0.044 (3)	−0.002 (2)	0.012 (2)	0.000 (2)
C4	0.032 (3)	0.042 (3)	0.033 (3)	−0.005 (2)	−0.004 (2)	−0.001 (2)
C5	0.035 (3)	0.035 (3)	0.038 (3)	0.000 (2)	−0.010 (2)	−0.005 (2)
C6	0.036 (3)	0.044 (3)	0.030 (3)	−0.001 (2)	−0.001 (2)	0.006 (2)
C7	0.050 (3)	0.038 (3)	0.025 (2)	−0.003 (2)	−0.004 (2)	0.002 (2)
I1	0.0478 (3)	0.0875 (4)	0.0468 (3)	0.0116 (2)	−0.00472 (19)	−0.0100 (2)
I2	0.0379 (3)	0.0668 (4)	0.0508 (4)	0.0012 (2)	−0.0021 (2)	−0.0218 (3)

O1—C4	1.231 (6)	C1—H1	0.9300
O2—C4	1.259 (6)	C2—C3	1.339 (7)
O2—H2O	1.224 (4)	C2—H2	0.9300
O3—C6	1.297 (6)	C3—H3	0.9300
O3—H3O	0.81 (8)	C4—C5	1.516 (7)
O4—C6	1.199 (7)	C5—H5A	0.9700
N1—C1	1.323 (6)	C5—H5B	0.9700
N1—C3	1.384 (6)	C6—C7	1.500 (7)
N1—C5	1.467 (6)	C7—H7A	0.9700
N2—C1	1.316 (6)	C7—H7B	0.9700
N2—C2	1.380 (6)	I1—I2	2.9192 (6)
N2—C7	1.459 (6)	I2—I1i	2.9192 (6)
C4—O2—H2O	125 (4)	O1—C4—C5	118.1 (5)
C6—O3—H3O	112 (6)	O2—C4—C5	116.0 (5)
C1—N1—C3	108.5 (4)	N1—C5—C4	112.6 (4)
C1—N1—C5	126.2 (4)	N1—C5—H5A	109.1
C3—N1—C5	125.1 (4)	C4—C5—H5A	109.1
C1—N2—C2	108.9 (4)	N1—C5—H5B	109.1
C1—N2—C7	127.3 (4)	C4—C5—H5B	109.1
C2—N2—C7	123.7 (4)	H5A—C5—H5B	107.8
N2—C1—N1	108.7 (4)	O4—C6—O3	124.9 (5)
N2—C1—H1	125.7	O4—C6—C7	125.0 (5)
N1—C1—H1	125.7	O3—C6—C7	110.0 (5)
C3—C2—N2	107.0 (4)	N2—C7—C6	111.7 (4)
C3—C2—H2	126.5	N2—C7—H7A	109.3
N2—C2—H2	126.5	C6—C7—H7A	109.3
C2—C3—N1	106.9 (5)	N2—C7—H7B	109.3
C2—C3—H3	126.6	C6—C7—H7B	109.3
N1—C3—H3	126.6	H7A—C7—H7B	107.9
O1—C4—O2	125.8 (5)	I1i—I2—I1	180.0

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O1ii	0.81 (8)	1.80 (8)	2.591 (6)	166 (9)
O2—H2O···O2iii	1.22 (1)	1.22 (1)	2.449 (6)	179 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O1i	0.81 (8)	1.80 (8)	2.591 (6)	166 (9)
O2—H2O⋯O2ii	1.224 (4)	1.224 (4)	2.449 (6)	179 (9)

Symmetry codes: (i) ; (ii) .