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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o649.
Published online 2010 February 17. doi:  10.1107/S1600536810004939
PMCID: PMC2983526

2-Phenyl­imidazolium acetate

Abstract

There are two 2-phenyl­imidazole cations and two acetate anions in the asymmetric unit of the title mol­ecular salt, C9H9N2 +·C2H3O2 . The dihredral angles between the five- and six-membered rings are 5.50 (2) and 6.90 (2)° in the two molecules. The structure is stabilized by N—H(...)O and weak C—H(...)O hydrogen-bonding inter­actions between the cations and anions, resulting in chains propagating in [110].

Related literature

For related structures, see: Liu et al. (2008 [triangle]); Yang et al. (2008 [triangle]); Xia et al. (2009 [triangle]).

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Object name is e-66-0o649-scheme1.jpg

Experimental

Crystal data

  • C9H9N2 +·C2H3O2
  • M r = 204.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o649-efi1.jpg
  • a = 10.0320 (6) Å
  • b = 11.0043 (7) Å
  • c = 19.3936 (9) Å
  • β = 97.982 (5)°
  • V = 2120.2 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.21 × 0.18 × 0.17 mm

Data collection

  • Oxford Diffraction Gemini R Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 [triangle]) T min = 0.57, T max = 0.81
  • 9257 measured reflections
  • 4331 independent reflections
  • 2142 reflections with I > 2 σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.114
  • S = 0.82
  • 4331 reflections
  • 272 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.16 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004939/pv2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004939/pv2258Isup2.hkl

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

Acknowledgments

We thank Yuncheng University for support.

supplementary crystallographic information

Comment

2-Phenylimidazole has been extensively used to build supramolecular architectures (Liu et al., 2008; Yang et al., 2008). Continuing our research in this important field (Xia et al., 2009), we now report the preparation and crystal structure of the title compound, (I).

There are two 2-phenylimidazole cations and two acetate anions in the asymmetric unit of the title compound (Fig. 1). In the crystal, the cations and anions are linked into chains along [110] by the N—H···O H–bonding interactions (Table 1) thus stabilizing the structure. The structure is further stabilized by rather weak non-classical interactions of the type C—H···O.

Experimental

A mixture of 2-phenylimidazole (0.5 mmol), CH3COOH (0.5 mmol) and H2O (30 mmol) was mixed. After one week, colorless crystals of (I) were yielded at room temperature (27% yield).

Refinement

All H atoms on C and N atoms were positioned geometrically (N—H = 0.86 Å and C—H = 0.93 and 0.96 Å for aryl and methyl H-atoms, respectively) and refined as riding, with Uiso(H) = 1.5Ueq(methyl-C atoms) and 1.2Ueq(the rest of the carrier C/N atoms).

Figures

Fig. 1.
The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C9H9N2+·C2H3O2F(000) = 864
Mr = 204.23Dx = 1.280 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4331 reflections
a = 10.0320 (6) Åθ = 2.1–26.4°
b = 11.0043 (7) ŵ = 0.09 mm1
c = 19.3936 (9) ÅT = 293 K
β = 97.982 (5)°Block, colorless
V = 2120.2 (2) Å30.21 × 0.18 × 0.17 mm
Z = 8

Data collection

Oxford Diffraction Gemini R Ultra diffractometer4331 independent reflections
Radiation source: fine-focus sealed tube2142 reflections with I > 2.o σ(I)
graphiteRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 26.4°, θmin = 2.1°
ω scanh = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)k = −9→13
Tmin = 0.57, Tmax = 0.81l = −18→24
9257 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.114w = 1/[σ2(Fo2) + (0.0675P)2] where P = (Fo2 + 2Fc2)/3
S = 0.82(Δ/σ)max = 0.001
4331 reflectionsΔρmax = 0.17 e Å3
272 parametersΔρmin = −0.16 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0175 (15)

Special details

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.

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

xyzUiso*/Ueq
C10.03640 (17)0.18563 (16)0.46297 (8)0.0512 (5)
C20.1416 (2)0.1044 (2)0.46747 (10)0.0877 (7)
H2A0.20150.09940.50850.105*
C30.1595 (3)0.0308 (2)0.41253 (11)0.1005 (9)
H3A0.2313−0.02330.41670.121*
C40.0733 (2)0.03613 (19)0.35197 (10)0.0788 (6)
H4A0.0856−0.01390.31470.095*
C5−0.0309 (2)0.1154 (2)0.34671 (11)0.0829 (7)
H5−0.09040.11960.30550.100*
C6−0.0498 (2)0.18957 (19)0.40128 (10)0.0732 (6)
H6−0.12200.24340.39650.088*
C70.01993 (17)0.26654 (16)0.52036 (8)0.0495 (4)
C80.05331 (19)0.36114 (18)0.62119 (9)0.0629 (5)
H80.08910.38290.66630.075*
C9−0.0501 (2)0.41439 (18)0.58166 (9)0.0683 (6)
H9−0.09920.48050.59430.082*
C100.5548 (2)0.2029 (2)0.49467 (11)0.0949 (8)
H100.58010.21310.54230.114*
C110.6097 (2)0.1266 (2)0.45397 (11)0.0956 (8)
H110.68070.07370.46790.115*
C120.44891 (18)0.22354 (17)0.38869 (9)0.0559 (5)
C130.35306 (17)0.26213 (15)0.32912 (8)0.0504 (4)
C140.3567 (2)0.2150 (2)0.26411 (10)0.0761 (6)
H140.42470.16090.25700.091*
C150.2611 (2)0.2466 (2)0.20906 (10)0.0883 (7)
H150.26480.21280.16540.106*
C160.1615 (2)0.32649 (19)0.21777 (10)0.0710 (6)
H160.09720.34780.18050.085*
C170.1577 (2)0.37441 (19)0.28156 (10)0.0806 (7)
H170.09010.42920.28820.097*
C180.2532 (2)0.34293 (19)0.33701 (10)0.0768 (6)
H180.24920.37740.38050.092*
C190.32986 (18)0.48865 (18)0.55858 (9)0.0571 (5)
C200.4364 (2)0.4355 (2)0.61201 (10)0.0811 (7)
H20A0.43950.47980.65480.122*
H20B0.52220.44080.59560.122*
H20C0.41570.35180.61980.122*
C210.30718 (17)0.07402 (17)0.69394 (8)0.0518 (5)
C220.2379 (2)0.14122 (19)0.74594 (10)0.0787 (6)
H22A0.25430.10060.79010.118*
H22B0.14290.14350.73030.118*
H22C0.27220.22270.75080.118*
N1−0.07063 (15)0.35460 (14)0.51965 (7)0.0600 (4)
H1−0.13230.37120.48560.072*
N20.09625 (14)0.26903 (13)0.58294 (6)0.0540 (4)
H20.16160.22030.59660.065*
N30.45439 (16)0.26380 (15)0.45407 (7)0.0711 (5)
H30.40340.31870.46810.085*
N40.54380 (16)0.13943 (14)0.38802 (7)0.0701 (5)
H40.56080.09970.35200.084*
O10.26407 (14)0.57803 (13)0.57651 (6)0.0737 (4)
O20.31032 (13)0.44328 (12)0.49935 (6)0.0750 (4)
O30.29723 (12)0.11352 (12)0.63317 (6)0.0673 (4)
O40.37241 (12)−0.02072 (11)0.71421 (5)0.0642 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0531 (11)0.0512 (11)0.0485 (10)0.0027 (9)0.0046 (8)0.0053 (8)
C20.1034 (17)0.0981 (17)0.0551 (12)0.0501 (14)−0.0114 (11)−0.0115 (12)
C30.118 (2)0.1063 (19)0.0703 (14)0.0594 (16)−0.0112 (13)−0.0202 (13)
C40.0918 (16)0.0745 (15)0.0666 (13)0.0126 (13)−0.0009 (11)−0.0162 (11)
C50.0869 (16)0.0860 (16)0.0676 (13)0.0161 (13)−0.0186 (11)−0.0186 (12)
C60.0732 (14)0.0746 (14)0.0667 (12)0.0202 (11)−0.0086 (10)−0.0083 (11)
C70.0524 (11)0.0502 (11)0.0460 (9)0.0071 (9)0.0076 (8)0.0084 (8)
C80.0749 (13)0.0677 (14)0.0461 (9)0.0115 (11)0.0084 (9)−0.0007 (10)
C90.0818 (14)0.0701 (14)0.0532 (11)0.0242 (11)0.0107 (10)−0.0026 (10)
C100.1201 (19)0.1024 (19)0.0555 (12)0.0555 (16)−0.0113 (12)−0.0029 (12)
C110.1139 (19)0.1034 (19)0.0626 (13)0.0610 (16)−0.0123 (12)0.0016 (13)
C120.0571 (12)0.0536 (12)0.0560 (11)0.0114 (9)0.0041 (8)0.0002 (9)
C130.0475 (10)0.0484 (11)0.0533 (10)0.0040 (9)0.0002 (8)−0.0026 (8)
C140.0737 (14)0.0895 (16)0.0623 (12)0.0335 (12)−0.0003 (10)−0.0080 (11)
C150.0917 (17)0.1143 (19)0.0546 (12)0.0340 (15)−0.0044 (11)−0.0150 (12)
C160.0619 (13)0.0847 (15)0.0610 (12)0.0135 (11)−0.0106 (10)−0.0015 (11)
C170.0730 (14)0.0889 (16)0.0731 (13)0.0335 (12)−0.0144 (11)−0.0154 (12)
C180.0798 (14)0.0843 (15)0.0598 (11)0.0301 (12)−0.0129 (10)−0.0202 (11)
C190.0555 (11)0.0621 (13)0.0525 (11)0.0081 (10)0.0036 (9)0.0016 (10)
C200.0828 (15)0.0834 (16)0.0703 (13)0.0202 (12)−0.0138 (11)0.0009 (11)
C210.0486 (10)0.0578 (12)0.0454 (10)0.0007 (9)−0.0057 (8)−0.0034 (9)
C220.1009 (16)0.0776 (15)0.0563 (11)0.0177 (13)0.0065 (10)−0.0068 (11)
N10.0645 (10)0.0650 (10)0.0488 (9)0.0173 (8)0.0021 (7)0.0056 (8)
N20.0579 (9)0.0567 (10)0.0467 (8)0.0109 (7)0.0045 (7)0.0057 (7)
N30.0800 (11)0.0759 (12)0.0542 (9)0.0321 (9)−0.0024 (8)−0.0026 (8)
N40.0808 (11)0.0694 (11)0.0567 (9)0.0303 (9)−0.0022 (8)−0.0028 (8)
O10.0818 (9)0.0766 (10)0.0590 (8)0.0280 (8)−0.0030 (6)−0.0086 (7)
O20.0823 (10)0.0845 (10)0.0550 (8)0.0301 (8)−0.0018 (7)−0.0102 (7)
O30.0727 (9)0.0785 (10)0.0495 (7)0.0216 (7)0.0042 (6)0.0081 (6)
O40.0705 (9)0.0657 (9)0.0519 (7)0.0191 (7)−0.0074 (6)0.0006 (6)

Geometric parameters (Å, °)

C1—C21.376 (2)C13—C181.364 (2)
C1—C61.376 (2)C13—C141.369 (2)
C1—C71.453 (2)C14—C151.377 (2)
C2—C31.370 (3)C14—H140.9300
C2—H2A0.9300C15—C161.359 (3)
C3—C41.360 (3)C15—H150.9300
C3—H3A0.9300C16—C171.350 (3)
C4—C51.354 (3)C16—H160.9300
C4—H4A0.9300C17—C181.381 (2)
C5—C61.370 (3)C17—H170.9300
C5—H50.9300C18—H180.9300
C6—H60.9300C19—O21.2429 (19)
C7—N11.327 (2)C19—O11.260 (2)
C7—N21.3425 (19)C19—C201.500 (2)
C8—C91.337 (2)C20—H20A0.9600
C8—N21.361 (2)C20—H20B0.9600
C8—H80.9300C20—H20C0.9600
C9—N11.361 (2)C21—O31.2470 (19)
C9—H90.9300C21—O41.264 (2)
C10—C111.323 (3)C21—C221.497 (3)
C10—N31.366 (2)C22—H22A0.9600
C10—H100.9300C22—H22B0.9600
C11—N41.363 (2)C22—H22C0.9600
C11—H110.9300N1—H10.8600
C12—N41.329 (2)N2—H20.8600
C12—N31.337 (2)N3—H30.8600
C12—C131.460 (2)N4—H40.8600
C2—C1—C6117.35 (17)C16—C15—C14120.78 (19)
C2—C1—C7121.14 (15)C16—C15—H15119.6
C6—C1—C7121.48 (16)C14—C15—H15119.6
C3—C2—C1121.11 (17)C17—C16—C15118.79 (17)
C3—C2—H2A119.4C17—C16—H16120.6
C1—C2—H2A119.4C15—C16—H16120.6
C4—C3—C2120.7 (2)C16—C17—C18120.70 (19)
C4—C3—H3A119.7C16—C17—H17119.6
C2—C3—H3A119.7C18—C17—H17119.6
C5—C4—C3119.0 (2)C13—C18—C17121.13 (18)
C5—C4—H4A120.5C13—C18—H18119.4
C3—C4—H4A120.5C17—C18—H18119.4
C4—C5—C6120.92 (18)O2—C19—O1123.17 (15)
C4—C5—H5119.5O2—C19—C20119.18 (18)
C6—C5—H5119.5O1—C19—C20117.65 (16)
C5—C6—C1120.98 (19)C19—C20—H20A109.5
C5—C6—H6119.5C19—C20—H20B109.5
C1—C6—H6119.5H20A—C20—H20B109.5
N1—C7—N2107.34 (15)C19—C20—H20C109.5
N1—C7—C1126.18 (14)H20A—C20—H20C109.5
N2—C7—C1126.44 (15)H20B—C20—H20C109.5
C9—C8—N2107.04 (15)O3—C21—O4123.46 (17)
C9—C8—H8126.5O3—C21—C22118.73 (16)
N2—C8—H8126.5O4—C21—C22117.81 (16)
C8—C9—N1107.77 (17)C21—C22—H22A109.5
C8—C9—H9126.1C21—C22—H22B109.5
N1—C9—H9126.1H22A—C22—H22B109.5
C11—C10—N3107.58 (17)C21—C22—H22C109.5
C11—C10—H10126.2H22A—C22—H22C109.5
N3—C10—H10126.2H22B—C22—H22C109.5
C10—C11—N4107.85 (17)C7—N1—C9108.93 (14)
C10—C11—H11126.1C7—N1—H1125.5
N4—C11—H11126.1C9—N1—H1125.5
N4—C12—N3107.75 (14)C7—N2—C8108.91 (14)
N4—C12—C13126.08 (16)C7—N2—H2125.5
N3—C12—C13126.14 (17)C8—N2—H2125.5
C18—C13—C14117.67 (15)C12—N3—C10108.30 (16)
C18—C13—C12120.96 (16)C12—N3—H3125.9
C14—C13—C12121.32 (17)C10—N3—H3125.9
C13—C14—C15120.93 (19)C12—N4—C11108.52 (16)
C13—C14—H14119.5C12—N4—H4125.7
C15—C14—H14119.5C11—N4—H4125.7

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.861.752.606 (2)172
N2—H2···O30.861.862.720 (2)175
N3—H3···O20.861.812.667 (2)175
N4—H4···O4ii0.861.762.609 (2)169
C2—H2A···O30.932.483.374 (2)161
C6—H6···O1i0.932.523.407 (3)158
C8—H8···O4iii0.932.533.430 (2)164
C14—H14···O4ii0.932.553.439 (2)159
C18—H18···O20.932.413.309 (2)162

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2258).

References

  • Liu, Y.-Y., Ma, J.-F., Yang, J., Ma, J.-C. & Ping, G.-J. (2008). CrystEngCommun, 10, 565–572.
  • Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xia, D.-C., Li, W.-C. & Han, S. (2009). Acta Cryst. E65, o3283. [PMC free article] [PubMed]
  • Yang, J., Ma, J.-F., Batten, S. R. & Su, Z.-M. (2008). Chem. Commun. pp. 2233–2235. [PubMed]

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