5-Carb-oxy-1,3-bis-(carb-oxy-meth-yl)-4-imidazolinium-4-carboxyl-ate.

The title compound, C(9)H(8)N(2)O(8), was obtained by the reaction of imidazole-4,5-dicarb-oxy-lic acid and 2-chloro-acetic acid. An intra-molecular O-H⋯O hydrogen bond occurs. The crystal packing is stabilized by intermolecular O-H⋯O and C-H⋯O hydrogen bonds, which link mol-ecules into a three-dimensional network.

Related literature

The title compound is a potential polydentate ligand for the construction of metal-organic frameworks. For applications of n class="Chemical">metal-organic frameworks, see: Gao et al. (2005 ▶); Gurunatha et al. (2008 ▶); Wang et al. (2010 ▶); Zhang & Li (2010 ▶). For related structures, see: Chai et al. (2010 ▶); Liu et al. (2004 ▶); Lu et al. (2006 ▶).

Experimental

Crystal data

C9H8N2O8

M = 272.17

Orthorhombic,

a = 8.986 (7) Å

b = 7.041 (6) Å

c = 33.68 (3) Å

V = 2131 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.15 mm−1

T = 296 K

0.35 × 0.33 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.948, T max = 0.957

13878 measured reflections

2091 independent reflections

1750 reflections with I2s(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.109

S = 0.98

2091 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 datablock(s) I, global. DOI: 10.1107/S160053681105416X/rz2687sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105416X/rz2687Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681105416X/rz2687Isup3.cml

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

C9H8N2O8	Dx = 1.697 Mg m−3
Mr = 272.17	Melting point: 510 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5190 reflections
a = 8.986 (7) Å	θ = 2.4–27.8°
b = 7.041 (6) Å	µ = 0.15 mm−1
c = 33.68 (3) Å	T = 296 K
V = 2131 (3) Å3	Block, red
Z = 8	0.35 × 0.33 × 0.29 mm
F(000) = 1120

Bruker APEXII CCD diffractometer	2091 independent reflections
Radiation source: fine-focus sealed tube	1750 reflections with I2s(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.948, Tmax = 0.957	k = −8→8
13878 measured reflections	l = −40→41

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0398P)2 + 2.3475P] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
2091 reflections	Δρmax = 0.23 e Å−3
185 parameters	Δρmin = −0.19 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: 0.065 (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
C1	0.0333 (2)	0.0455 (3)	0.36566 (6)	0.0294 (5)
H1	0.0683	−0.0768	0.3610	0.035*
C2	−0.0421 (2)	0.3049 (3)	0.39610 (6)	0.0259 (5)
C3	−0.0421 (2)	0.3386 (3)	0.35616 (6)	0.0254 (5)
C4	0.0345 (2)	0.1384 (3)	0.29562 (6)	0.0298 (5)
H4A	−0.0453	0.1904	0.2796	0.036*
H4B	0.0406	0.0030	0.2906	0.036*
C5	0.1801 (3)	0.2329 (3)	0.28505 (6)	0.0347 (5)
C6	0.0369 (2)	0.0165 (3)	0.43809 (6)	0.0309 (5)
H6A	0.0273	−0.1192	0.4338	0.037*
H6B	−0.0339	0.0537	0.4584	0.037*
C7	0.1931 (3)	0.0624 (3)	0.45163 (6)	0.0322 (5)
C8	−0.0809 (2)	0.5139 (3)	0.33270 (6)	0.0312 (5)
C9	−0.0854 (2)	0.4261 (3)	0.43069 (6)	0.0311 (5)
N1	0.00421 (19)	0.1725 (2)	0.33789 (5)	0.0266 (4)
N2	0.00520 (19)	0.1186 (2)	0.40108 (5)	0.0267 (4)
O1	−0.0529 (2)	0.5150 (2)	0.29686 (4)	0.0433 (5)
O2	−0.1404 (2)	0.6492 (2)	0.35153 (5)	0.0467 (5)
O3	−0.1520 (2)	0.5842 (2)	0.42221 (5)	0.0436 (5)
O4	−0.0606 (2)	0.3734 (2)	0.46442 (4)	0.0417 (4)
O5	0.2115 (2)	0.2377 (3)	0.24692 (5)	0.0528 (6)
O6	0.2616 (2)	0.2993 (3)	0.30957 (5)	0.0522 (5)
O7	0.28441 (18)	0.1355 (3)	0.43067 (5)	0.0459 (5)
O8	0.2134 (2)	0.0069 (3)	0.48852 (5)	0.0479 (5)
H2W	0.149 (4)	0.170 (5)	0.2306 (9)	0.075 (10)*
H1W	0.306 (4)	0.045 (5)	0.4978 (10)	0.082 (11)*
H3W	−0.149 (4)	0.617 (4)	0.3891 (9)	0.073 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0302 (11)	0.0273 (11)	0.0306 (11)	0.0000 (9)	0.0007 (9)	−0.0047 (9)
C2	0.0233 (10)	0.0260 (10)	0.0285 (10)	0.0003 (8)	0.0004 (8)	−0.0012 (8)
C3	0.0234 (10)	0.0266 (10)	0.0261 (10)	0.0016 (8)	0.0002 (8)	−0.0027 (8)
C4	0.0333 (12)	0.0328 (11)	0.0234 (10)	−0.0017 (10)	0.0005 (8)	−0.0077 (9)
C5	0.0314 (12)	0.0384 (12)	0.0343 (12)	−0.0035 (10)	0.0044 (9)	−0.0126 (10)
C6	0.0355 (12)	0.0286 (11)	0.0286 (11)	0.0000 (9)	0.0000 (9)	0.0057 (9)
C7	0.0398 (13)	0.0273 (11)	0.0294 (11)	0.0014 (10)	−0.0019 (10)	−0.0004 (9)
C8	0.0317 (12)	0.0322 (12)	0.0296 (11)	0.0003 (10)	−0.0018 (9)	0.0019 (9)
C9	0.0301 (11)	0.0343 (12)	0.0290 (11)	−0.0012 (10)	0.0036 (9)	−0.0052 (9)
N1	0.0282 (9)	0.0283 (9)	0.0234 (9)	−0.0004 (8)	0.0012 (7)	−0.0043 (7)
N2	0.0298 (9)	0.0264 (9)	0.0240 (8)	0.0006 (8)	0.0001 (7)	−0.0002 (7)
O1	0.0579 (11)	0.0434 (10)	0.0286 (8)	0.0069 (8)	0.0023 (7)	0.0058 (7)
O2	0.0662 (12)	0.0343 (9)	0.0397 (9)	0.0182 (9)	0.0040 (8)	0.0020 (8)
O3	0.0539 (11)	0.0401 (10)	0.0368 (9)	0.0166 (8)	0.0043 (8)	−0.0083 (7)
O4	0.0550 (11)	0.0451 (10)	0.0249 (8)	0.0022 (9)	0.0033 (7)	−0.0049 (7)
O5	0.0522 (12)	0.0692 (13)	0.0370 (9)	−0.0241 (10)	0.0166 (8)	−0.0153 (9)
O6	0.0413 (10)	0.0652 (13)	0.0501 (10)	−0.0177 (9)	−0.0020 (8)	−0.0202 (9)
O7	0.0388 (10)	0.0537 (11)	0.0452 (10)	−0.0106 (9)	−0.0016 (8)	0.0126 (9)
O8	0.0497 (11)	0.0645 (12)	0.0296 (9)	−0.0099 (10)	−0.0091 (8)	0.0080 (8)

C1—N1	1.320 (3)	C6—N2	1.467 (3)
C1—N2	1.324 (3)	C6—C7	1.511 (3)
C1—H1	0.9300	C6—H6A	0.9700
C2—C3	1.366 (3)	C6—H6B	0.9700
C2—N2	1.389 (3)	C7—O7	1.199 (3)
C2—C9	1.496 (3)	C7—O8	1.316 (3)
C3—N1	1.385 (3)	C8—O1	1.233 (3)
C3—C8	1.506 (3)	C8—O2	1.263 (3)
C4—N1	1.469 (3)	C9—O4	1.216 (3)
C4—C5	1.511 (3)	C9—O3	1.295 (3)
C4—H4A	0.9700	O2—H3W	1.29 (3)
C4—H4B	0.9700	O3—H3W	1.14 (3)
C5—O6	1.199 (3)	O5—H2W	0.92 (3)
C5—O5	1.315 (3)	O8—H1W	0.93 (4)
N1—C1—N2	109.72 (19)	C7—C6—H6B	109.8
N1—C1—H1	125.1	H6A—C6—H6B	108.2
N2—C1—H1	125.1	O7—C7—O8	126.1 (2)
C3—C2—N2	106.45 (17)	O7—C7—C6	123.4 (2)
C3—C2—C9	131.9 (2)	O8—C7—C6	110.53 (19)
N2—C2—C9	121.62 (19)	O1—C8—O2	125.0 (2)
C2—C3—N1	106.91 (18)	O1—C8—C3	118.1 (2)
C2—C3—C8	131.23 (19)	O2—C8—C3	116.90 (19)
N1—C3—C8	121.86 (18)	O4—C9—O3	123.6 (2)
N1—C4—C5	108.45 (17)	O4—C9—C2	120.4 (2)
N1—C4—H4A	110.0	O3—C9—C2	116.01 (19)
C5—C4—H4A	110.0	C1—N1—C3	108.44 (18)
N1—C4—H4B	110.0	C1—N1—C4	122.60 (18)
C5—C4—H4B	110.0	C3—N1—C4	128.64 (17)
H4A—C4—H4B	108.4	C1—N2—C2	108.46 (18)
O6—C5—O5	122.1 (2)	C1—N2—C6	122.56 (19)
O6—C5—C4	122.6 (2)	C2—N2—C6	128.68 (17)
O5—C5—C4	115.28 (19)	C8—O2—H3W	112.5 (14)
N2—C6—C7	109.38 (17)	C9—O3—H3W	112.0 (16)
N2—C6—H6A	109.8	C5—O5—H2W	116 (2)
C7—C6—H6A	109.8	C7—O8—H1W	111 (2)
N2—C6—H6B	109.8
N2—C2—C3—N1	0.3 (2)	N2—C1—N1—C3	1.4 (2)
C9—C2—C3—N1	−177.8 (2)	N2—C1—N1—C4	175.52 (18)
N2—C2—C3—C8	−179.3 (2)	C2—C3—N1—C1	−1.1 (2)
C9—C2—C3—C8	2.5 (4)	C8—C3—N1—C1	178.64 (18)
N1—C4—C5—O6	9.2 (3)	C2—C3—N1—C4	−174.69 (19)
N1—C4—C5—O5	−170.7 (2)	C8—C3—N1—C4	5.0 (3)
N2—C6—C7—O7	−15.1 (3)	C5—C4—N1—C1	−98.9 (2)
N2—C6—C7—O8	166.48 (18)	C5—C4—N1—C3	74.0 (3)
C2—C3—C8—O1	170.6 (2)	N1—C1—N2—C2	−1.2 (2)
N1—C3—C8—O1	−9.0 (3)	N1—C1—N2—C6	−175.48 (18)
C2—C3—C8—O2	−9.5 (3)	C3—C2—N2—C1	0.5 (2)
N1—C3—C8—O2	170.9 (2)	C9—C2—N2—C1	178.88 (18)
C3—C2—C9—O4	−171.7 (2)	C3—C2—N2—C6	174.33 (19)
N2—C2—C9—O4	10.4 (3)	C9—C2—N2—C6	−7.3 (3)
C3—C2—C9—O3	9.6 (3)	C7—C6—N2—C1	90.0 (2)
N2—C2—C9—O3	−168.3 (2)	C7—C6—N2—C2	−83.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3W···O2	1.13 (3)	1.29 (3)	2.426 (3)	177 (3)
C1—H1···O6i	0.93	2.47	3.158 (3)	131
C4—H4A···O5ii	0.97	2.38	3.311 (3)	160
C4—H4B···O6i	0.97	2.37	3.046 (3)	126
C6—H6A···O7i	0.97	2.42	3.136 (4)	130
C6—H6B···O8iii	0.97	2.44	3.346 (3)	154
O5—H2W···O1iv	0.92 (3)	1.67 (3)	2.581 (3)	170 (3)
O8—H1W···O4v	0.93 (4)	1.84 (4)	2.710 (3)	155 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3W⋯O2	1.13 (3)	1.29 (3)	2.426 (3)	177 (3)
C1—H1⋯O6i	0.93	2.47	3.158 (3)	131
C4—H4A⋯O5ii	0.97	2.38	3.311 (3)	160
C4—H4B⋯O6i	0.97	2.37	3.046 (3)	126
C6—H6A⋯O7i	0.97	2.42	3.136 (4)	130
C6—H6B⋯O8iii	0.97	2.44	3.346 (3)	154
O5—H2W⋯O1iv	0.92 (3)	1.67 (3)	2.581 (3)	170 (3)
O8—H1W⋯O4v	0.93 (4)	1.84 (4)	2.710 (3)	155 (3)

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