(S)-2-(1H-Imidazol-1-yl)succinic acid.

The title compound, C(7)H(8)N(2)O(4), is a zwitterion, [formal name = (S)-3-carb-oxy-2-(imidazol-3-ium-1-yl)propano-ate], in which the deproton-ated negatively charged carboxyl-ate end shows almost identical C-O bond distances [1.248 (4) and 1.251 (4) Å] due to resonance. The mol-ecules are involved in inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, which define a tightly bound three-dimensional structure.

Related literature

For the use of imidazol-1-ylalkanoic acids as probes to determine the intra­cellular and extracellular pH and cell volume by 1H NMR, see: López et al.(1996 ▶). For the preparation of the title compound, see: Bao et al. (2003 ▶).

Experimental

Crystal data

C7H8N2O4

M = 184.15

Orthorhombic,

a = 7.3212 (16) Å

b = 7.9193 (16) Å

c = 14.254 (3) Å

V = 826.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.25 × 0.20 × 0.18 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.97, T max = 0.98

8489 measured reflections

1110 independent reflections

952 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.151

S = 1.12

1110 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015220/bg2234sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015220/bg2234Isup2.hkl

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

C7H8N2O4	F(000) = 384
Mr = 184.15	Dx = 1.480 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2ac 2ab	Cell parameters from 2123 reflections
a = 7.3212 (16) Å	θ = 2.8–27.4°
b = 7.9193 (16) Å	µ = 0.12 mm−1
c = 14.254 (3) Å	T = 293 K
V = 826.4 (3) Å3	Prism, colorless
Z = 4	0.25 × 0.20 × 0.18 mm

Rigaku Mercury2 diffractometer	1110 independent reflections
Radiation source: fine-focus sealed tube	952 reflections with I > 2σ(I)
graphite	Rint = 0.053
CCD_Profile_fitting scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −9→9
Tmin = 0.97, Tmax = 0.98	k = −10→10
8489 measured reflections	l = −18→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0852P)2 + 0.2196P] where P = (Fo2 + 2Fc2)/3
1110 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.9679 (4)	0.2336 (4)	0.6099 (2)	0.0299 (7)
C2	0.9073 (4)	0.4110 (4)	0.6415 (2)	0.0309 (7)
H2A	0.9846	0.4450	0.6943	0.037*
C3	0.9360 (5)	0.5376 (4)	0.5624 (2)	0.0367 (7)
H3A	1.0554	0.5197	0.5346	0.044*
H3B	0.8447	0.5193	0.5142	0.044*
C4	0.9226 (5)	0.7177 (4)	0.5977 (2)	0.0378 (7)
C5	0.6549 (5)	0.4474 (5)	0.7626 (3)	0.0493 (10)
H5	0.7259	0.4826	0.8130	0.059*
C6	0.4741 (6)	0.4230 (7)	0.7635 (3)	0.0640 (13)
H6	0.3962	0.4380	0.8144	0.077*
C7	0.5708 (5)	0.3653 (5)	0.6236 (3)	0.0422 (8)
H7	0.5719	0.3333	0.5608	0.051*
N1	0.7172 (3)	0.4110 (3)	0.67364 (18)	0.0314 (6)
N2	0.4268 (4)	0.3725 (4)	0.6766 (2)	0.0507 (8)
H2	0.3175	0.3487	0.6589	0.061*
O1	0.8474 (4)	0.1251 (3)	0.5944 (2)	0.0507 (7)
O2	1.1355 (3)	0.2163 (3)	0.59668 (16)	0.0409 (6)
O3	0.9107 (5)	0.8279 (3)	0.52925 (19)	0.0584 (9)
H3C	0.8908	0.9290	0.5489	0.070*
O4	0.9181 (5)	0.7543 (4)	0.67883 (19)	0.0638 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0279 (14)	0.0283 (15)	0.0334 (15)	0.0011 (12)	−0.0001 (12)	0.0036 (13)
C2	0.0315 (15)	0.0274 (15)	0.0338 (15)	−0.0038 (13)	0.0014 (13)	−0.0015 (12)
C3	0.0455 (18)	0.0265 (15)	0.0382 (16)	0.0006 (15)	0.0092 (16)	0.0019 (12)
C4	0.0396 (17)	0.0287 (15)	0.0452 (18)	0.0001 (15)	0.0057 (15)	0.0020 (14)
C5	0.0390 (19)	0.064 (3)	0.045 (2)	−0.0105 (19)	0.0083 (16)	−0.0169 (19)
C6	0.055 (2)	0.077 (3)	0.061 (2)	−0.014 (2)	0.024 (2)	−0.022 (3)
C7	0.0345 (16)	0.0433 (19)	0.0486 (18)	0.0050 (17)	−0.0069 (16)	−0.0066 (15)
N1	0.0293 (13)	0.0301 (13)	0.0349 (14)	−0.0001 (11)	−0.0025 (11)	−0.0032 (11)
N2	0.0310 (14)	0.0487 (18)	0.072 (2)	−0.0010 (15)	−0.0041 (16)	−0.0126 (16)
O1	0.0411 (13)	0.0241 (12)	0.087 (2)	−0.0010 (10)	0.0034 (14)	−0.0071 (13)
O2	0.0350 (12)	0.0383 (13)	0.0494 (14)	0.0044 (10)	0.0047 (11)	−0.0035 (11)
O3	0.090 (2)	0.0294 (13)	0.0560 (15)	0.0060 (15)	0.0122 (16)	0.0052 (11)
O4	0.106 (3)	0.0381 (14)	0.0472 (15)	0.0013 (17)	−0.0113 (17)	−0.0097 (12)

C1—O2	1.249 (4)	C5—C6	1.338 (6)
C1—O1	1.251 (4)	C5—N1	1.378 (4)
C1—C2	1.541 (4)	C5—H5	0.9300
C2—N1	1.465 (4)	C6—N2	1.347 (6)
C2—C3	1.522 (4)	C6—H6	0.9300
C2—H2A	0.9800	C7—N2	1.299 (5)
C3—C4	1.516 (4)	C7—N1	1.338 (4)
C3—H3A	0.9700	C7—H7	0.9300
C3—H3B	0.9700	N2—H2	0.8600
C4—O4	1.193 (4)	O3—H3C	0.8601
C4—O3	1.312 (4)
O2—C1—O1	126.3 (3)	O3—C4—C3	112.6 (3)
O2—C1—C2	115.3 (3)	C6—C5—N1	107.9 (4)
O1—C1—C2	118.3 (3)	C6—C5—H5	126.1
N1—C2—C3	111.3 (3)	N1—C5—H5	126.1
N1—C2—C1	111.4 (2)	C5—C6—N2	106.7 (3)
C3—C2—C1	110.1 (2)	C5—C6—H6	126.6
N1—C2—H2A	108.0	N2—C6—H6	126.6
C3—C2—H2A	108.0	N2—C7—N1	109.1 (3)
C1—C2—H2A	108.0	N2—C7—H7	125.4
C4—C3—C2	111.4 (3)	N1—C7—H7	125.4
C4—C3—H3A	109.3	C7—N1—C5	106.4 (3)
C2—C3—H3A	109.3	C7—N1—C2	126.5 (3)
C4—C3—H3B	109.3	C5—N1—C2	127.1 (3)
C2—C3—H3B	109.3	C7—N2—C6	109.9 (3)
H3A—C3—H3B	108.0	C7—N2—H2	125.1
O4—C4—O3	123.8 (3)	C6—N2—H2	125.1
O4—C4—C3	123.6 (3)	C4—O3—H3C	112.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.86	1.91	2.716 (4)	155
O3—H3C···O1ii	0.86	1.71	2.572 (3)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	1.91	2.716 (4)	155
O3—H3C⋯O1ii	0.86	1.71	2.572 (3)	177

Symmetry codes: (i) ; (ii) .