2-Phenyl-1H-imidazol-3-ium hydrogen oxalate.

In the title mol-ecular salt, C(9)H(9)N(2) (+)·C(2)HO(4) (-), the dihedral angle between the aromatic rings of the cation is 17.5 (3)° and the dihedral angle between the -CO(2)H and -CO(2) groups of the anion is 38.6 (2)°. In the crystal, the components inter-act by way of O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For backgrond to 2-phenyl­imidazole as a ligand, see: Liu et al. (2008 ▶). For a related 2-phenyl­imidazolium nitrate structure, see: Zhang et al. (2007 ▶).

Experimental

Crystal data

C9H9N2 +·C2HO4 −

M = 234.21

Triclinic,

a = 5.571 (4) Å

b = 9.216 (5) Å

c = 11.918 (6) Å

α = 70.262 (5)°

β = 80.460 (1)°

γ = 74.871 (5)°

V = 554.0 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.22 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Gemini R Ultra CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.38, T max = 0.57

4030 measured reflections

2505 independent reflections

1629 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.104

S = 0.93

2505 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; 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) global, I. DOI: 10.1107/S1600536811023300/hb5908sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023300/hb5908Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023300/hb5908Isup3.cml

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

C9H9N2+·C2HO4−	Z = 2
Mr = 234.21	F(000) = 244
Triclinic, P1	Dx = 1.404 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.571 (4) Å	Cell parameters from 2505 reflections
b = 9.216 (5) Å	θ = 1.8–29.1°
c = 11.918 (6) Å	µ = 0.11 mm−1
α = 70.262 (5)°	T = 293 K
β = 80.460 (1)°	Block, colorless
γ = 74.871 (5)°	0.22 × 0.20 × 0.15 mm
V = 554.0 (6) Å3

Oxford Diffraction Gemini R Ultra CCD diffractometer	2505 independent reflections
Radiation source: fine-focus sealed tube	1629 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 29.1°, θmin = 1.8°
ω scans	h = −5→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −9→11
Tmin = 0.38, Tmax = 0.57	l = −14→16
4030 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0587P)2] where P = (Fo2 + 2Fc2)/3
2505 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.38 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
C1	−0.1534 (2)	0.24120 (16)	0.80993 (12)	0.0329 (3)
C2	0.0697 (2)	0.30067 (16)	0.82279 (12)	0.0351 (3)
C3	0.2653 (3)	0.6592 (2)	0.61457 (15)	0.0559 (4)
H3	0.4206	0.5901	0.6257	0.067*
C4	0.1280 (4)	0.6664 (2)	0.52534 (17)	0.0712 (6)
H4	0.1910	0.6018	0.4770	0.085*
C5	−0.1001 (4)	0.7681 (2)	0.50819 (16)	0.0685 (5)
H5	−0.1925	0.7726	0.4484	0.082*
C6	−0.1917 (3)	0.8628 (2)	0.57895 (16)	0.0605 (5)
H6	−0.3468	0.9319	0.5669	0.073*
C7	−0.0578 (3)	0.85767 (18)	0.66808 (14)	0.0463 (4)
H7	−0.1221	0.9234	0.7154	0.056*
C8	0.1728 (3)	0.75450 (16)	0.68720 (12)	0.0364 (3)
C9	0.3166 (2)	0.74777 (15)	0.78093 (12)	0.0329 (3)
C11	0.4589 (3)	0.81235 (18)	0.91542 (13)	0.0451 (4)
H11	0.4762	0.8682	0.9645	0.054*
C10	0.5995 (3)	0.67346 (17)	0.91074 (13)	0.0414 (4)
H10	0.7336	0.6140	0.9556	0.050*
N1	0.5092 (2)	0.63481 (12)	0.82744 (10)	0.0363 (3)
H1	0.5683	0.5498	0.8079	0.044*
N2	0.2843 (2)	0.85814 (13)	0.83489 (11)	0.0409 (3)
H2	0.1713	0.9444	0.8211	0.049*
O1	0.04670 (19)	0.40133 (14)	0.86821 (12)	0.0591 (3)
O2	0.27912 (17)	0.22797 (13)	0.78035 (11)	0.0565 (3)
H2A	0.3941	0.2626	0.7889	0.085*
O3	−0.12709 (18)	0.09884 (11)	0.82754 (11)	0.0547 (3)
O4	−0.35046 (16)	0.34460 (11)	0.78500 (9)	0.0420 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0231 (6)	0.0340 (8)	0.0460 (8)	−0.0023 (6)	−0.0051 (6)	−0.0198 (6)
C2	0.0249 (7)	0.0331 (8)	0.0510 (9)	−0.0015 (6)	−0.0098 (6)	−0.0183 (7)
C3	0.0585 (11)	0.0547 (10)	0.0585 (10)	−0.0027 (8)	−0.0167 (8)	−0.0242 (8)
C4	0.0890 (15)	0.0786 (14)	0.0595 (11)	−0.0185 (12)	−0.0179 (11)	−0.0330 (10)
C5	0.0738 (14)	0.0881 (15)	0.0521 (11)	−0.0333 (12)	−0.0248 (10)	−0.0119 (10)
C6	0.0459 (10)	0.0726 (12)	0.0573 (10)	−0.0132 (9)	−0.0182 (8)	−0.0063 (9)
C7	0.0400 (8)	0.0490 (9)	0.0468 (9)	−0.0089 (7)	−0.0087 (7)	−0.0094 (7)
C8	0.0383 (8)	0.0332 (8)	0.0379 (8)	−0.0103 (6)	−0.0067 (6)	−0.0080 (6)
C9	0.0322 (7)	0.0257 (7)	0.0399 (8)	−0.0042 (6)	−0.0030 (6)	−0.0106 (6)
C11	0.0470 (9)	0.0474 (9)	0.0493 (9)	−0.0059 (7)	−0.0126 (7)	−0.0252 (7)
C10	0.0403 (8)	0.0394 (8)	0.0453 (8)	−0.0024 (7)	−0.0139 (7)	−0.0142 (7)
N1	0.0371 (6)	0.0279 (6)	0.0441 (7)	0.0010 (5)	−0.0094 (5)	−0.0148 (5)
N2	0.0380 (7)	0.0308 (6)	0.0551 (8)	0.0034 (5)	−0.0114 (6)	−0.0195 (6)
O1	0.0379 (6)	0.0655 (8)	0.0974 (9)	−0.0077 (5)	−0.0096 (6)	−0.0560 (7)
O2	0.0216 (5)	0.0618 (7)	0.1047 (9)	−0.0057 (5)	−0.0051 (5)	−0.0522 (7)
O3	0.0314 (5)	0.0331 (6)	0.1060 (9)	−0.0020 (4)	−0.0108 (6)	−0.0311 (6)
O4	0.0235 (5)	0.0358 (6)	0.0717 (7)	0.0009 (4)	−0.0142 (5)	−0.0241 (5)

C1—O3	1.2291 (17)	C7—C8	1.385 (2)
C1—O4	1.2541 (16)	C7—H7	0.9300
C1—C2	1.531 (2)	C8—C9	1.455 (2)
C2—O1	1.1934 (17)	C9—N1	1.3293 (18)
C2—O2	1.3003 (16)	C9—N2	1.3374 (17)
C3—C8	1.384 (2)	C11—C10	1.329 (2)
C3—C4	1.385 (2)	C11—N2	1.366 (2)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.368 (3)	C10—N1	1.3649 (19)
C4—H4	0.9300	C10—H10	0.9300
C5—C6	1.362 (3)	N1—H1	0.8600
C5—H5	0.9300	N2—H2	0.8600
C6—C7	1.378 (2)	O2—H2A	0.8200
C6—H6	0.9300
O3—C1—O4	126.05 (12)	C8—C7—H7	120.0
O3—C1—C2	118.29 (11)	C3—C8—C7	118.80 (14)
O4—C1—C2	115.64 (12)	C3—C8—C9	120.56 (14)
O1—C2—O2	125.70 (13)	C7—C8—C9	120.64 (13)
O1—C2—C1	122.10 (12)	N1—C9—N2	106.32 (12)
O2—C2—C1	112.19 (12)	N1—C9—C8	127.46 (12)
C8—C3—C4	120.32 (17)	N2—C9—C8	126.19 (12)
C8—C3—H3	119.8	C10—C11—N2	107.50 (13)
C4—C3—H3	119.8	C10—C11—H11	126.3
C5—C4—C3	120.15 (18)	N2—C11—H11	126.3
C5—C4—H4	119.9	C11—C10—N1	106.80 (13)
C3—C4—H4	119.9	C11—C10—H10	126.6
C6—C5—C4	119.83 (17)	N1—C10—H10	126.6
C6—C5—H5	120.1	C9—N1—C10	110.07 (11)
C4—C5—H5	120.1	C9—N1—H1	125.0
C5—C6—C7	120.91 (17)	C10—N1—H1	125.0
C5—C6—H6	119.5	C9—N2—C11	109.30 (12)
C7—C6—H6	119.5	C9—N2—H2	125.3
C6—C7—C8	120.00 (16)	C11—N2—H2	125.3
C6—C7—H7	120.0	C2—O2—H2A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O4i	0.82	1.76	2.5793 (19)	172
N2—H2···O3ii	0.86	1.90	2.732 (2)	164
N1—H1···O4i	0.86	1.93	2.777 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O4i	0.82	1.76	2.5793 (19)	172
N2—H2⋯O3ii	0.86	1.90	2.732 (2)	164
N1—H1⋯O4i	0.86	1.93	2.777 (2)	169

Symmetry codes: (i) ; (ii) .