2-Phenyl­imidazolium nitrate monohydrate

Dao-Cheng Xia; Wan-Cheng Li; Shuang Han

doi:10.1107/S1600536809050703

. 2009 Nov 28;65(Pt 12):o3283. doi: 10.1107/S1600536809050703

2-Phenylimidazolium nitrate monohydrate

Dao-Cheng Xia ^a,^*, Wan-Cheng Li ^b, Shuang Han ^a

PMCID: PMC2972149 PMID: 21578976

Abstract

In the title hydrated molecular salt, C₉H₉N₂ ⁺·NO₃ ⁻·H₂O, the dihedral angle between the aromatic rings in the cation is 11.09 (8)°. In the crystal, the components are linked into chains propagating in [101] by N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For related structures containing 2-phenylimidazole, see: Liu et al. (2008 ▶); Yang et al. (2008 ▶). graphic file with name e-65-o3283-scheme1.jpg

Experimental

Crystal data

C₉H₉N₂ ⁺·NO₃ ⁻·H₂O
M _r = 225.21
Monoclinic,
a = 8.026 (4) Å
b = 14.951 (7) Å
c = 8.895 (5) Å
β = 101.096 (5)°
V = 1047.4 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.33 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.56, T _max = 0.81
4388 measured reflections
2407 independent reflections
1430 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.104
S = 0.88
2407 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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/S1600536809050703/hb5245sup1.cif

e-65-o3283-sup1.cif^{(14.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050703/hb5245Isup2.hkl

e-65-o3283-Isup2.hkl^{(115.9KB, 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
N2—H2⋯O1W	0.86	1.92	2.753 (2)	163
N3—H3⋯O1ⁱ	0.86	1.94	2.7809 (17)	166
O1W—HW11⋯O2ⁱⁱ	0.83 (2)	2.21 (2)	2.989 (2)	155.3 (19)
O1W—HW12⋯O2	0.87 (2)	2.07 (2)	2.905 (2)	162.3 (19)

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

Acknowledgments

We thank Yuncheng University and Jilin University for support.

supplementary crystallographic information

Comment

2-Phenylimidazole, as an important N-containing ligand with excellent coordinating abilities and fruitful aromatic systems, have been extensively used to build supramolecular architectures (Liu et al., 2008; Yang et al., 2008). We report here the synthesis and structure of the title compound, namely, C₉H₁₁N₃O₄ (I)

There are one 2-phenylimidazole cation, one nitrate anion and one water molecule in the asymmetric unit of the title compound, C₉H₁₁N₃O₄ (Fig. 1). In the crystal, molecules are linked into layer structures by N—H···O and O—H···O H-bonding interactions (Table 1).

Experimental

A mixture of Cu(NO₃)₂^.2.5H₂O (0.5 mmol), 2-phenylimidazole (0.5 mmol), and H₂O (30 mmol) was heated in a sealed vessel at 413 K for 2 days. After the mixture was slowly cooled to room temperature, colorless blocks of (I) were obtained (23% yield).