2-Phenyl-1H-imidazol-3-ium hydrogen fumarate-fumaric acid (2/1).

The asymmetric unit of the title compound, C(9)H(9)N(2) (+)·C(4)H(3)O(4) (-)·0.5C(4)H(4)O(4), consists of one 2-phenyl-imidazolium cation, one hydrogen fumarate anion and half a fumaric acid mol-ecule, which lies on an inversion center. N-H⋯O and O-H⋯O hydrogen bonds connect the cations, anions and fumaric acid mol-ecules into sheets parallel to the (102) plane.

Related literature

For similar structures, see: Jiang (2009 ▶); Song (2011 ▶); Xia & Yao (2010 ▶).

Experimental

Crystal data

C9H9N2 +·C4H3O4 −·0.5C4H4O4

M = 318.28

Monoclinic,

a = 9.572 (3) Å

b = 19.276 (4) Å

c = 8.289 (5) Å

β = 106.480 (3)°

V = 1466.6 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.18 × 0.15 × 0.14 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.980, T max = 0.984

11042 measured reflections

2675 independent reflections

1963 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.091

S = 1.00

2675 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005557/yk2037sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005557/yk2037Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005557/yk2037Isup3.cml

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

C9H9N2+·C4H3O4−·0.5C4H4O4	F(000) = 664
Mr = 318.28	Dx = 1.441 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2675 reflections
a = 9.572 (3) Å	θ = 2.2–25.3°
b = 19.276 (4) Å	µ = 0.11 mm−1
c = 8.289 (5) Å	T = 293 K
β = 106.480 (3)°	Block, colorless
V = 1466.6 (10) Å3	0.18 × 0.15 × 0.14 mm
Z = 4

Oxford Diffraction Gemini R Ultra diffractometer	2675 independent reflections
Radiation source: fine-focus sealed tube	1963 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 10.0 pixels mm-1	θmax = 25.3°, θmin = 2.2°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = 0→23
Tmin = 0.980, Tmax = 0.984	l = 0→9
11042 measured reflections

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-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0574P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
2675 reflections	Δρmax = 0.21 e Å−3
209 parameters	Δρmin = −0.25 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: 0.0068 (12)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.30636 (17)	0.70313 (7)	0.15392 (19)	0.0466 (4)
H1	0.2295	0.6753	0.0948	0.056*
C2	0.51445 (15)	0.73599 (6)	0.33290 (17)	0.0339 (3)
C3	0.31826 (17)	0.77144 (7)	0.1375 (2)	0.0458 (4)
H3	0.2516	0.8002	0.0642	0.055*
C4	0.65236 (15)	0.73529 (6)	0.46476 (17)	0.0361 (3)
C5	0.71012 (18)	0.67306 (7)	0.53922 (19)	0.0441 (4)
H5	0.6609	0.6317	0.5041	0.053*
C6	0.83936 (19)	0.67245 (8)	0.6642 (2)	0.0531 (4)
H6	0.8772	0.6306	0.7138	0.064*
C7	0.91375 (19)	0.73335 (8)	0.7170 (2)	0.0559 (4)
H7	1.0020	0.7325	0.8011	0.067*
C8	0.85745 (19)	0.79517 (8)	0.6455 (2)	0.0554 (4)
H8	0.9075	0.8363	0.6817	0.067*
C9	0.72735 (18)	0.79677 (7)	0.52033 (19)	0.0464 (4)
H9	0.6894	0.8389	0.4728	0.056*
C10	0.50312 (14)	0.48691 (6)	0.25178 (15)	0.0284 (3)
C11	0.63137 (14)	0.50545 (6)	0.19048 (15)	0.0316 (3)
H11	0.6584	0.5519	0.1930	0.038*
C12	0.70748 (14)	0.46016 (7)	0.13372 (15)	0.0329 (3)
H12	0.6801	0.4138	0.1308	0.039*
C13	0.83360 (14)	0.47805 (7)	0.07425 (15)	0.0299 (3)
C14	0.13846 (14)	0.54984 (6)	0.41335 (15)	0.0306 (3)
C15	0.01299 (14)	0.53111 (7)	0.47557 (15)	0.0325 (3)
H15	−0.0525	0.5661	0.4804	0.039*
N1	0.42847 (13)	0.68174 (5)	0.27399 (15)	0.0414 (3)
H1A	0.4472	0.6396	0.3068	0.050*
N2	0.44703 (13)	0.79138 (5)	0.24890 (14)	0.0389 (3)
H2A	0.4796	0.8332	0.2627	0.047*
O1	0.46797 (11)	0.42536 (4)	0.25506 (12)	0.0448 (3)
O2	0.43619 (9)	0.53724 (4)	0.29443 (11)	0.0356 (2)
O3	0.21778 (10)	0.49744 (5)	0.39383 (12)	0.0462 (3)
H3A	0.2850	0.5114	0.3593	0.055*
O4	0.16258 (11)	0.60952 (5)	0.38435 (13)	0.0482 (3)
O5	0.90474 (11)	0.42773 (5)	0.03852 (12)	0.0447 (3)
H5A	0.9724	0.4427	0.0065	0.054*
O6	0.86586 (11)	0.54051 (5)	0.06280 (12)	0.0453 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0451 (10)	0.0360 (8)	0.0582 (9)	−0.0057 (7)	0.0139 (8)	−0.0014 (7)
C2	0.0424 (9)	0.0209 (6)	0.0464 (8)	−0.0019 (6)	0.0256 (7)	0.0009 (6)
C3	0.0454 (10)	0.0354 (8)	0.0562 (9)	0.0006 (6)	0.0137 (8)	0.0061 (7)
C4	0.0423 (9)	0.0277 (7)	0.0453 (8)	−0.0013 (6)	0.0241 (7)	0.0002 (6)
C5	0.0561 (11)	0.0288 (7)	0.0516 (9)	0.0015 (6)	0.0221 (8)	0.0008 (6)
C6	0.0614 (12)	0.0431 (9)	0.0549 (10)	0.0113 (8)	0.0165 (9)	0.0079 (7)
C7	0.0523 (11)	0.0583 (11)	0.0544 (10)	0.0015 (8)	0.0106 (8)	0.0029 (8)
C8	0.0592 (12)	0.0439 (9)	0.0607 (10)	−0.0144 (8)	0.0131 (9)	−0.0017 (8)
C9	0.0550 (11)	0.0289 (8)	0.0565 (9)	−0.0039 (7)	0.0176 (8)	0.0036 (7)
C10	0.0279 (7)	0.0247 (7)	0.0349 (7)	0.0016 (5)	0.0125 (6)	0.0001 (5)
C11	0.0305 (8)	0.0263 (6)	0.0411 (8)	−0.0017 (5)	0.0150 (6)	−0.0001 (5)
C12	0.0300 (8)	0.0292 (7)	0.0428 (8)	−0.0025 (5)	0.0156 (6)	−0.0018 (6)
C13	0.0266 (7)	0.0314 (7)	0.0332 (7)	0.0007 (6)	0.0109 (6)	−0.0024 (5)
C14	0.0297 (7)	0.0290 (7)	0.0351 (7)	−0.0016 (6)	0.0122 (6)	−0.0021 (5)
C15	0.0279 (7)	0.0335 (6)	0.0394 (7)	0.0011 (6)	0.0150 (6)	−0.0023 (6)
N1	0.0488 (8)	0.0220 (6)	0.0566 (8)	−0.0036 (5)	0.0202 (6)	0.0024 (5)
N2	0.0456 (8)	0.0211 (5)	0.0543 (7)	−0.0024 (5)	0.0211 (6)	0.0033 (5)
O1	0.0463 (6)	0.0222 (5)	0.0781 (7)	−0.0021 (4)	0.0375 (6)	−0.0028 (4)
O2	0.0352 (6)	0.0235 (5)	0.0566 (6)	0.0021 (4)	0.0271 (5)	−0.0006 (4)
O3	0.0433 (6)	0.0322 (5)	0.0782 (7)	0.0002 (4)	0.0418 (6)	0.0038 (5)
O4	0.0498 (7)	0.0303 (6)	0.0741 (7)	−0.0033 (4)	0.0329 (6)	0.0027 (5)
O5	0.0381 (6)	0.0384 (6)	0.0694 (7)	0.0005 (4)	0.0343 (5)	−0.0041 (5)
O6	0.0446 (6)	0.0320 (6)	0.0692 (7)	−0.0033 (4)	0.0324 (5)	−0.0017 (5)

C1—C3	1.332 (2)	C10—O1	1.2357 (14)
C1—N1	1.3663 (19)	C10—O2	1.2669 (15)
C1—H1	0.9300	C10—C11	1.4989 (18)
C2—N1	1.3346 (16)	C11—C12	1.3072 (18)
C2—N2	1.3366 (17)	C11—H11	0.9300
C2—C4	1.456 (2)	C12—C13	1.4686 (18)
C3—N2	1.3687 (19)	C12—H12	0.9300
C3—H3	0.9300	C13—O6	1.2532 (15)
C4—C5	1.3899 (19)	C13—O5	1.2676 (15)
C4—C9	1.3944 (19)	C14—O4	1.2108 (15)
C5—C6	1.370 (2)	C14—O3	1.3009 (15)
C5—H5	0.9300	C14—C15	1.4799 (18)
C6—C7	1.378 (2)	C15—C15i	1.312 (3)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.372 (2)	N1—H1A	0.8592
C7—H7	0.9300	N2—H2A	0.8602
C8—C9	1.377 (2)	O3—H3A	0.8203
C8—H8	0.9300	O5—H5A	0.8193
C9—H9	0.9300
C3—C1—N1	107.00 (13)	O1—C10—O2	124.52 (12)
C3—C1—H1	126.5	O1—C10—C11	119.39 (11)
N1—C1—H1	126.5	O2—C10—C11	116.08 (11)
N1—C2—N2	106.19 (12)	C12—C11—C10	123.81 (12)
N1—C2—C4	126.96 (11)	C12—C11—H11	118.1
N2—C2—C4	126.84 (11)	C10—C11—H11	118.1
C1—C3—N2	107.20 (13)	C11—C12—C13	124.00 (12)
C1—C3—H3	126.4	C11—C12—H12	118.0
N2—C3—H3	126.4	C13—C12—H12	118.0
C5—C4—C9	118.96 (14)	O6—C13—O5	123.87 (12)
C5—C4—C2	120.21 (12)	O6—C13—C12	119.64 (11)
C9—C4—C2	120.82 (12)	O5—C13—C12	116.49 (11)
C6—C5—C4	120.22 (13)	O4—C14—O3	124.20 (12)
C6—C5—H5	119.9	O4—C14—C15	121.35 (12)
C4—C5—H5	119.9	O3—C14—C15	114.45 (11)
C5—C6—C7	120.47 (14)	C15i—C15—C14	125.05 (16)
C5—C6—H6	119.8	C15i—C15—H15	117.5
C7—C6—H6	119.8	C14—C15—H15	117.5
C8—C7—C6	119.90 (16)	C2—N1—C1	109.96 (11)
C8—C7—H7	120.0	C2—N1—H1A	125.0
C6—C7—H7	120.0	C1—N1—H1A	125.1
C7—C8—C9	120.39 (14)	C2—N2—C3	109.65 (11)
C7—C8—H8	119.8	C2—N2—H2A	125.2
C9—C8—H8	119.8	C3—N2—H2A	125.2
C8—C9—C4	120.05 (13)	C14—O3—H3A	109.4
C8—C9—H9	120.0	C13—O5—H5A	109.5
C4—C9—H9	120.0
N1—C1—C3—N2	−0.55 (17)	O1—C10—C11—C12	2.4 (2)
N1—C2—C4—C5	2.4 (2)	O2—C10—C11—C12	−176.38 (12)
N2—C2—C4—C5	−179.07 (12)	C10—C11—C12—C13	−179.71 (11)
N1—C2—C4—C9	−176.51 (13)	C11—C12—C13—O6	−6.1 (2)
N2—C2—C4—C9	2.0 (2)	C11—C12—C13—O5	173.31 (12)
C9—C4—C5—C6	−0.5 (2)	O4—C14—C15—C15i	−173.42 (16)
C2—C4—C5—C6	−179.49 (13)	O3—C14—C15—C15i	6.5 (2)
C4—C5—C6—C7	−0.3 (2)	N2—C2—N1—C1	−0.52 (15)
C5—C6—C7—C8	0.7 (2)	C4—C2—N1—C1	178.24 (13)
C6—C7—C8—C9	−0.4 (3)	C3—C1—N1—C2	0.67 (17)
C7—C8—C9—C4	−0.4 (2)	N1—C2—N2—C3	0.17 (15)
C5—C4—C9—C8	0.9 (2)	C4—C2—N2—C3	−178.59 (12)
C2—C4—C9—C8	179.82 (13)	C1—C3—N2—C2	0.24 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	1.75	2.5721 (14)	176
O5—H5A···O6ii	0.82	1.83	2.6360 (14)	169
N1—H1A···O2	0.86	1.98	2.7903 (15)	157
N2—H2A···O1iii	0.86	1.86	2.7106 (14)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82	1.75	2.5721 (14)	176
O5—H5A⋯O6i	0.82	1.83	2.6360 (14)	169
N1—H1A⋯O2	0.86	1.98	2.7903 (15)	157
N2—H2A⋯O1ii	0.86	1.86	2.7106 (14)	168

Symmetry codes: (i) ; (ii) .