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

Guo, H.; Zhang, X.; Li, J.-X.

doi:10.1107/S1600536812005557

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1021

doi:10.1107/S1600536812005557

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

Hong Guo,^a ^* Xin Zhang ^a and Jian-Xia Li ^a

^aInstitute of Applied Chemistry, Shenyang University of Chemical Technology, Shenyang 110142, People's Republic of China
^*Correspondence e-mail: gh2103@163.com

(Received 15 December 2011; accepted 8 February 2012; online 10 March 2012)

The asymmetric unit of the title compound, C₉H₉N₂⁺·C₄H₃O₄⁻·0.5C₄H₄O₄, consists of one 2-phenylimidazolium cation, one hydrogen fumarate anion and half a fumaric acid molecule, which lies on an inversion center. N—H⋯O and O—H⋯O hydrogen bonds connect the cations, anions and fumaric acid molecules 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_r = 318.28
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.980, T_max = 0.984
11042 measured reflections
2675 independent reflections
1963 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.091
S = 1.00
2675 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) -x+2, -y+1, -z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005557/yk2037sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812005557/yk2037Isup3.cml

checkCIF report

Comment top

Noncovalent hydrogen-bonding interactions have attracted great interest for chemists because of their physicochemical properties (Jiang, 2009). 2-Phenylimidazole can be used to form various supramolecular architectures with anions such as acetate (Xia & Yao, 2010) and hydrogen oxalate (Song, 2011). In this work, we report the crystal structure of the title compound prepared from 2-phenylimidazole and fumaric acid.

The asymmetric unit of the title compound contains one 2-phenylimidazolium cation, one hydrogen fumarate anion and a half of fumaric acid (Fig. 1). The fumaric acid molecule lies on an inversion center. N—H···O and O—H···O hydrogen bonds connect the cations, anions and fumaric acid molecules into sheets parallel to the (1 0 2) plane (Fig. 2, Table 1).

Related literature top

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

Experimental top

2-Phenylimidazole (2 mmol), fumaric acid (1 mmol) and ethanol (15 ml) were mixed. Colorless crystals were obtained by slow evaporation of the solution at room temperature after three days.

Structure description top

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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis CCD (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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level. Dashed lines denote hydrogen bonds. [Symmetry code: (i) -x, 1-y, 1-z.]
	Fig. 2. The two-dimensional network connected by hydrogen bonds (dashed lines).

2-Phenyl-1H-imidazol-3-ium 3-carboxyprop-2-enoate–fumaric acid (2/1) top

Crystal data top

C₉H₉N₂⁺·C₄H₃O₄⁻·0.5C₄H₄O₄	F(000) = 664
M_r = 318.28	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0574P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2675 reflections	Δρ_max = 0.21 e Å⁻³
209 parameters	Δρ_min = −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)

Crystal data top

C₉H₉N₂⁺·C₄H₃O₄⁻·0.5C₄H₄O₄	V = 1466.6 (10) Å³
M_r = 318.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.572 (3) Å	µ = 0.11 mm⁻¹
b = 19.276 (4) Å	T = 293 K
c = 8.289 (5) Å	0.18 × 0.15 × 0.14 mm
β = 106.480 (3)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	2675 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1963 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.984	R_int = 0.000
11042 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
2675 reflections	Δρ_min = −0.25 e Å⁻³
209 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (ii) −x+2, −y+1, −z; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₉N₂⁺·C₄H₃O₄⁻·0.5C₄H₄O₄
M_r	318.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.572 (3), 19.276 (4), 8.289 (5)
β (°)	106.480 (3)
V (Å³)	1466.6 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.18 × 0.15 × 0.14

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.980, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	11042, 2675, 1963
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.091, 1.00
No. of reflections	2675
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2.

References

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Volume 68| Part 4| April 2012| Page o1021

doi:10.1107/S1600536812005557

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