Imidazolium fumarate.

In the title compound, C(3)H(5)N(2) (+)·C(4)H(3)O(4) (-), the dihedral angle between the imidazolium ring and the plane formed by the fumarate anion is 80.98 (6)°. In the crystal structure, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds form extended chains along [100] and [01], creating a two-dimensional network.

Related literature

For background information on the anti-pyretic and anti-inflamatory biological activity of imidazole derivatives, see: Tudek et al. (1992 ▶); Puig-Parellada et al. (1973 ▶). For fumaric acid, see: Bednowitz & Post (1966 ▶) and for imidazole, see: McMullan et al. (1979 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C3H5N2 +·C4H3O4 −

M = 184.15

Triclinic,

a = 7.4794 (4) Å

b = 7.7522 (3) Å

c = 8.4231 (4) Å

α = 69.695 (3)°

β = 81.415 (2)°

γ = 66.193 (2)°

V = 419.04 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 294 K

0.12 × 0.02 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

7824 measured reflections

1922 independent reflections

1443 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.149

S = 1.07

1922 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040793/lh2920sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040793/lh2920Isup2.hkl

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

C3H5N2+·C4H3O4−	Z = 2
Mr = 184.15	F(000) = 192
Triclinic, P1	Dx = 1.460 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4794 (4) Å	Cell parameters from 4127 reflections
b = 7.7522 (3) Å	θ = 2.6–27.5°
c = 8.4231 (4) Å	µ = 0.12 mm−1
α = 69.695 (3)°	T = 294 K
β = 81.415 (2)°	Prism, colourless
γ = 66.193 (2)°	0.12 × 0.02 × 0.02 mm
V = 419.04 (3) Å3

Nonius KappaCCD diffractometer	1443 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.087
graphite	θmax = 27.5°, θmin = 2.6°
CCD rotation images, thick slices scans	h = −9→8
7824 measured reflections	k = −10→10
1922 independent reflections	l = −10→10

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0832P)2 + 0.0432P] where P = (Fo2 + 2Fc2)/3
1922 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.29 e Å−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
O4	0.06367 (15)	0.14005 (15)	0.66024 (12)	0.0409 (3)
O2	0.71272 (18)	0.03156 (19)	0.86710 (14)	0.0507 (4)
O1	0.71448 (18)	0.2024 (2)	0.59326 (14)	0.0592 (4)
H1	0.8224	0.1913	0.6157	0.089*
O3	0.0768 (2)	0.3167 (2)	0.39170 (14)	0.0587 (4)
N1	0.8197 (2)	0.25796 (19)	0.13620 (16)	0.0466 (4)
H9	0.8473	0.1397	0.2063	0.056*
N2	0.8081 (2)	0.4960 (2)	−0.09082 (16)	0.0443 (4)
H8	0.8267	0.5605	−0.1937	0.053*
C2	0.4385 (2)	0.1246 (2)	0.70462 (18)	0.0380 (4)
H2	0.3770	0.0624	0.7974	0.046*
C4	0.1475 (2)	0.2259 (2)	0.53479 (17)	0.0365 (4)
C1	0.6358 (2)	0.1144 (2)	0.72978 (18)	0.0373 (4)
C3	0.3458 (2)	0.2155 (2)	0.56046 (18)	0.0415 (4)
H3	0.4073	0.2778	0.4678	0.050*
C5	0.8781 (3)	0.3027 (2)	−0.0231 (2)	0.0475 (4)
H5	0.9560	0.2119	−0.0781	0.057*
C6	0.7006 (3)	0.5786 (2)	0.0293 (2)	0.0493 (4)
H6	0.6342	0.7135	0.0147	0.059*
C7	0.7089 (3)	0.4285 (3)	0.1717 (2)	0.0485 (4)
H7	0.6500	0.4391	0.2751	0.058*

	U11	U22	U33	U12	U13	U23
O4	0.0376 (6)	0.0512 (6)	0.0305 (6)	−0.0243 (5)	−0.0008 (4)	0.0002 (5)
O2	0.0456 (7)	0.0681 (8)	0.0344 (6)	−0.0282 (6)	−0.0079 (5)	−0.0006 (5)
O1	0.0435 (7)	0.0886 (9)	0.0388 (7)	−0.0404 (7)	−0.0064 (5)	0.0083 (6)
O3	0.0548 (8)	0.0869 (9)	0.0302 (6)	−0.0419 (7)	−0.0100 (5)	0.0079 (6)
N1	0.0564 (9)	0.0408 (7)	0.0368 (7)	−0.0217 (7)	−0.0059 (6)	0.0006 (5)
N2	0.0499 (8)	0.0517 (8)	0.0288 (6)	−0.0259 (7)	−0.0019 (6)	−0.0012 (5)
C2	0.0358 (8)	0.0450 (8)	0.0334 (7)	−0.0207 (7)	0.0019 (6)	−0.0072 (6)
C4	0.0369 (8)	0.0428 (7)	0.0278 (7)	−0.0196 (6)	−0.0013 (6)	−0.0033 (6)
C1	0.0354 (8)	0.0427 (7)	0.0317 (7)	−0.0180 (6)	−0.0013 (6)	−0.0051 (6)
C3	0.0380 (8)	0.0550 (9)	0.0317 (7)	−0.0264 (7)	0.0010 (6)	−0.0042 (6)
C5	0.0506 (10)	0.0498 (9)	0.0401 (9)	−0.0181 (8)	−0.0011 (7)	−0.0127 (7)
C6	0.0584 (11)	0.0412 (8)	0.0431 (9)	−0.0182 (8)	−0.0011 (8)	−0.0079 (7)
C7	0.0554 (10)	0.0546 (9)	0.0341 (8)	−0.0233 (8)	0.0028 (7)	−0.0109 (7)

O4—C4	1.2664 (17)	N2—H8	0.8600
O2—C1	1.2109 (18)	C2—C3	1.310 (2)
O1—C1	1.3084 (17)	C2—C1	1.489 (2)
O1—H1	0.8200	C2—H2	0.9300
O3—C4	1.2363 (17)	C4—C3	1.497 (2)
N1—C5	1.317 (2)	C3—H3	0.9300
N1—C7	1.356 (2)	C5—H5	0.9300
N1—H9	0.8600	C6—C7	1.339 (2)
N2—C5	1.307 (2)	C6—H6	0.9300
N2—C6	1.368 (2)	C7—H7	0.9300
C1—O1—H1	109.5	O2—C1—C2	121.36 (13)
C5—N1—C7	109.00 (14)	O1—C1—C2	114.43 (12)
C5—N1—H9	125.5	C2—C3—C4	124.42 (14)
C7—N1—H9	125.5	C2—C3—H3	117.8
C5—N2—C6	108.60 (13)	C4—C3—H3	117.8
C5—N2—H8	125.7	N2—C5—N1	108.58 (15)
C6—N2—H8	125.7	N2—C5—H5	125.7
C3—C2—C1	124.31 (14)	N1—C5—H5	125.7
C3—C2—H2	117.8	C7—C6—N2	107.01 (15)
C1—C2—H2	117.8	C7—C6—H6	126.5
O3—C4—O4	124.23 (14)	N2—C6—H6	126.5
O3—C4—C3	117.70 (13)	C6—C7—N1	106.81 (15)
O4—C4—C3	118.06 (12)	C6—C7—H7	126.6
O2—C1—O1	124.20 (13)	N1—C7—H7	126.6
C3—C2—C1—O2	178.47 (16)	C6—N2—C5—N1	−0.09 (19)
C3—C2—C1—O1	−1.1 (2)	C7—N1—C5—N2	−0.12 (19)
C1—C2—C3—C4	179.96 (13)	C5—N2—C6—C7	0.27 (19)
O3—C4—C3—C2	−179.96 (16)	N2—C6—C7—N1	−0.33 (19)
O4—C4—C3—C2	−0.5 (2)	C5—N1—C7—C6	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	1.75	2.5699 (16)	173
N2—H8···O3ii	0.86	1.82	2.6600 (18)	166
N1—H9···O4iii	0.86	1.94	2.7969 (16)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	1.75	2.5699 (16)	173
N2—H8⋯O3ii	0.86	1.82	2.6600 (18)	166
N1—H9⋯O4iii	0.86	1.94	2.7969 (16)	172

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