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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o609.
Published online 2010 February 13. doi:  10.1107/S1600536810004927
PMCID: PMC2983698

2-Phenyl­imidazole dihydrogen phosphate phospho­ric acid

Abstract

The crystal structure of the title compound, C9H9N2 +·H2PO4 ·H3PO4, is stabilized by N—H(...)O and O—H(...)O hydrogen-bonding inter­actions, resulting in a two-dimensional network.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-66-0o609-scheme1.jpg

Experimental

Crystal data

  • C9H9N2 +·H2PO4 ·H3PO4
  • M r = 340.16
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o609-efi1.jpg
  • a = 17.1875 (12) Å
  • b = 4.7220 (3) Å
  • c = 17.7585 (14) Å
  • β = 99.767 (7)°
  • V = 1420.38 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.35 mm−1
  • T = 293 K
  • 0.25 × 0.22 × 0.20 mm

Data collection

  • Oxford Diffraction Gemini R Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 [triangle]) T min = 0.61, T max = 0.84
  • 5555 measured reflections
  • 2893 independent reflections
  • 1549 reflections with I > 2.0 σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.080
  • S = 0.87
  • 2893 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 [triangle]); 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/S1600536810004927/pv2259sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004927/pv2259Isup2.hkl

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

Acknowledgments

We thank Yuncheng University for support.

supplementary crystallographic information

Comment

2-Phenylimidazole is a good candidate for building 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).

The asymmetric unit of the title compound contains one 2-phenylimidazole cation, one dihydrogen phosphate anion and one phosphoric acid molecule (Fig. 1). The structure is stabilized by the O—H···O and N—H···O H–bonding interactions (Table 1); a rather weak interaction of the type C—H···O is also present in the structure.

Experimental

A mixture of 2-phenylimidazole (0.5 mmol), phosphoric acid (1 mmol) and H2O (30 mmol) was mixed. After two weeks, colorless crystals of (I) were yielded at room temperature (18% yield).

Refinement

All H atoms on C and N atoms were positioned geometrically with distances O—H, N—H and C—H = 0.82, 0.86 and 0.93 Å, respectively, and were refined in riding mode, with Uiso(H) = 1.5Ueq(O) and 1.2Ueq(C/N).

Figures

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

Crystal data

C9H9N2+·H2PO4·H3PO4F(000) = 704
Mr = 340.16Dx = 1.591 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2893 reflections
a = 17.1875 (12) Åθ = 2.3–26.4°
b = 4.7220 (3) ŵ = 0.35 mm1
c = 17.7585 (14) ÅT = 293 K
β = 99.767 (7)°Block, colorless
V = 1420.38 (17) Å30.25 × 0.22 × 0.20 mm
Z = 4

Data collection

Oxford Diffraction Gemini R Ultra diffractometer2893 independent reflections
Radiation source: fine-focus sealed tube1549 reflections with I > 2.0 σ(I)
graphiteRint = 0.038
Detector resolution: 10.0 pixels mm-1θmax = 26.4°, θmin = 2.3°
ω scanh = −21→21
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)k = −5→4
Tmin = 0.61, Tmax = 0.84l = −13→22
5555 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 0.87w = 1/[σ2(Fo2) + (0.0302P)2] where P = (Fo2 + 2Fc2)/3
2893 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.37 e Å3

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
P10.21882 (4)−0.03732 (14)0.43687 (4)0.0302 (2)
P20.42236 (4)0.04439 (15)0.89806 (4)0.0299 (2)
O40.35030 (10)−0.0447 (4)0.84416 (10)0.0393 (5)
O50.28575 (10)0.0703 (4)0.50061 (9)0.0381 (5)
H5A0.30470.21620.48640.057*
O30.48015 (11)−0.2115 (3)0.91299 (11)0.0381 (5)
H3A0.5199−0.16350.94250.057*
O60.18630 (11)−0.3002 (3)0.46455 (11)0.0388 (5)
O20.40773 (10)0.1605 (4)0.97411 (10)0.0380 (5)
O70.25178 (11)−0.0717 (4)0.36199 (10)0.0428 (5)
H70.2877−0.18820.36820.064*
O10.46827 (11)0.2710 (4)0.85825 (11)0.0399 (5)
H10.43990.40910.84660.060*
O80.15458 (10)0.1928 (4)0.41974 (11)0.0405 (5)
H8A0.17380.33650.40450.061*
N20.26383 (14)0.5520 (5)0.61475 (12)0.0382 (6)
H20.23090.61520.57650.046*
N10.31292 (13)0.3278 (5)0.71534 (12)0.0395 (6)
H1B0.31760.21810.75450.047*
C50.16191 (18)0.0460 (7)0.72484 (19)0.0548 (9)
H50.20370.01780.76490.066*
C80.37239 (17)0.4892 (6)0.69554 (17)0.0443 (8)
H80.42420.49910.72120.053*
C60.17162 (16)0.2248 (6)0.66598 (16)0.0361 (7)
C30.0300 (2)−0.0510 (8)0.6673 (2)0.0657 (10)
H3−0.0174−0.14540.66760.079*
C90.34158 (17)0.6299 (6)0.63224 (17)0.0429 (8)
H90.36790.75650.60520.051*
C20.03804 (19)0.1260 (9)0.6094 (2)0.0719 (11)
H2A−0.00430.15310.56990.086*
C70.24664 (16)0.3649 (6)0.66528 (15)0.0332 (7)
C10.10825 (19)0.2679 (8)0.60773 (18)0.0604 (10)
H1A0.11280.39110.56780.072*
C40.0923 (2)−0.0905 (8)0.7256 (2)0.0691 (10)
H40.0870−0.21090.76580.083*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0327 (4)0.0264 (4)0.0305 (4)−0.0009 (3)0.0027 (3)−0.0005 (3)
P20.0291 (4)0.0297 (4)0.0301 (4)0.0019 (3)0.0027 (3)0.0022 (3)
O40.0320 (10)0.0512 (12)0.0313 (11)−0.0061 (9)−0.0042 (9)0.0072 (9)
O50.0402 (11)0.0425 (11)0.0293 (11)−0.0111 (9)−0.0012 (9)0.0036 (9)
O30.0348 (11)0.0290 (10)0.0457 (13)0.0045 (8)−0.0063 (9)−0.0022 (9)
O60.0451 (12)0.0271 (10)0.0430 (13)−0.0067 (9)0.0036 (10)−0.0010 (9)
O20.0331 (11)0.0520 (12)0.0283 (11)0.0102 (9)0.0033 (9)−0.0007 (9)
O70.0525 (13)0.0445 (12)0.0315 (12)0.0114 (10)0.0077 (9)0.0030 (9)
O10.0448 (12)0.0311 (10)0.0461 (13)0.0029 (9)0.0136 (10)0.0066 (9)
O80.0350 (12)0.0289 (10)0.0547 (15)0.0002 (9)−0.0011 (10)−0.0008 (9)
N20.0431 (15)0.0443 (14)0.0263 (14)0.0063 (12)0.0031 (11)0.0070 (12)
N10.0407 (16)0.0522 (15)0.0246 (14)−0.0007 (12)0.0023 (12)0.0090 (11)
C50.0418 (19)0.065 (2)0.054 (2)−0.0073 (17)−0.0042 (16)0.0145 (18)
C80.0353 (17)0.061 (2)0.0354 (18)−0.0041 (15)0.0028 (14)0.0083 (16)
C60.0346 (18)0.0438 (17)0.0296 (19)0.0066 (14)0.0049 (14)−0.0059 (14)
C30.042 (2)0.079 (3)0.077 (3)−0.0129 (19)0.013 (2)−0.012 (2)
C90.0433 (19)0.0520 (19)0.0337 (19)−0.0065 (16)0.0073 (15)0.0051 (15)
C20.041 (2)0.117 (3)0.051 (3)−0.001 (2)−0.0093 (18)−0.004 (2)
C70.0368 (17)0.0394 (16)0.0234 (16)0.0082 (14)0.0052 (14)−0.0019 (13)
C10.041 (2)0.097 (3)0.039 (2)−0.0023 (18)−0.0026 (17)0.0111 (18)
C40.051 (2)0.081 (3)0.074 (3)−0.0155 (19)0.007 (2)0.018 (2)

Geometric parameters (Å, °)

P1—O61.4790 (18)N1—C81.368 (3)
P1—O71.5400 (19)N1—H1B0.8600
P1—O81.5421 (18)C5—C41.361 (4)
P1—O51.5559 (17)C5—C61.376 (4)
P2—O41.4916 (18)C5—H50.9300
P2—O21.5175 (19)C8—C91.335 (4)
P2—O31.5579 (18)C8—H80.9300
P2—O11.568 (2)C6—C11.384 (4)
O5—H5A0.8200C6—C71.451 (4)
O3—H3A0.8200C3—C21.350 (5)
O7—H70.8200C3—C41.370 (4)
O1—H10.8200C3—H30.9300
O8—H8A0.8200C9—H90.9300
N2—C71.328 (3)C2—C11.385 (5)
N2—C91.370 (3)C2—H2A0.9300
N2—H20.8600C1—H1A0.9300
N1—C71.332 (3)C4—H40.9300
O6—P1—O7114.43 (11)C6—C5—H5119.4
O6—P1—O8111.01 (11)C9—C8—N1106.7 (3)
O7—P1—O8105.07 (11)C9—C8—H8126.7
O6—P1—O5107.86 (10)N1—C8—H8126.7
O7—P1—O5109.12 (10)C5—C6—C1118.5 (3)
O8—P1—O5109.25 (10)C5—C6—C7120.6 (3)
O4—P2—O2115.35 (11)C1—C6—C7120.9 (3)
O4—P2—O3109.06 (11)C2—C3—C4119.5 (3)
O2—P2—O3109.01 (10)C2—C3—H3120.3
O4—P2—O1109.26 (11)C4—C3—H3120.3
O2—P2—O1109.08 (11)C8—C9—N2106.8 (3)
O3—P2—O1104.53 (11)C8—C9—H9126.6
P1—O5—H5A109.5N2—C9—H9126.6
P2—O3—H3A109.5C3—C2—C1121.2 (3)
P1—O7—H7109.5C3—C2—H2A119.4
P2—O1—H1109.5C1—C2—H2A119.4
P1—O8—H8A109.5N2—C7—N1106.0 (2)
C7—N2—C9110.2 (2)N2—C7—C6127.5 (2)
C7—N2—H2124.9N1—C7—C6126.5 (3)
C9—N2—H2124.9C6—C1—C2119.4 (3)
C7—N1—C8110.3 (2)C6—C1—H1A120.3
C7—N1—H1B124.9C2—C1—H1A120.3
C8—N1—H1B124.9C5—C4—C3120.3 (3)
C4—C5—C6121.2 (3)C5—C4—H4119.9
C4—C5—H5119.4C3—C4—H4119.9

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5A···O2i0.821.912.563 (2)136
O3—H3A···O2ii0.821.762.546 (2)159
O8—H8A···O6iii0.822.012.553 (2)123
N2—H2···O6iii0.862.052.859 (3)157
N1—H1B···O40.862.022.871 (3)169
O7—H7···O4iv0.821.762.536 (3)158
O1—H1···O3iii0.822.192.625 (2)113
C9—H9···O5iii0.932.603.154 (3)119

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2259).

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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