2-Phenyl­imidazole dihydrogen phosphate phospho­ric acid

Dao-Cheng Xia; Ji-Huan Yao

doi:10.1107/S1600536810004927

. 2010 Feb 13;66(Pt 3):o609. doi: 10.1107/S1600536810004927

2-Phenylimidazole dihydrogen phosphate phosphoric acid

Dao-Cheng Xia ^a,^*, Ji-Huan Yao ^a

PMCID: PMC2983698 PMID: 21580368

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 ▶); Yang et al. (2008 ▶); Xia et al. (2009 ▶).

Experimental

Crystal data

C₉H₉N₂ ⁺·H₂PO₄ ⁻·H₃PO₄
M _r = 340.16
Monoclinic,
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 ▶) 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
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.37 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 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004927/pv2259sup1.cif

e-66-0o609-sup1.cif^{(16.2KB, cif)}

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

e-66-0o609-Isup2.hkl^{(139.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2ⁱ	0.82	1.91	2.563 (2)	136
O3—H3A⋯O2ⁱⁱ	0.82	1.76	2.546 (2)	159
O8—H8A⋯O6ⁱⁱⁱ	0.82	2.01	2.553 (2)	123
N2—H2⋯O6ⁱⁱⁱ	0.86	2.05	2.859 (3)	157
N1—H1B⋯O4	0.86	2.02	2.871 (3)	169
O7—H7⋯O4^iv	0.82	1.76	2.536 (3)	158
O1—H1⋯O3ⁱⁱⁱ	0.82	2.19	2.625 (2)	113

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

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).