(E)-1-[(2-Hy­droxy-1-naphth­yl)methyl­idene­amino]­imidazolidine-2,4-dione

Liang-Quan Sheng; Hua-Jie Xu; Na-Na Du; Xue-Yue Jiang

doi:10.1107/S1600536810020118

. 2010 Jun 9;66(Pt 7):o1601. doi: 10.1107/S1600536810020118

(E)-1-[(2-Hydroxy-1-naphthyl)methylideneamino]imidazolidine-2,4-dione

Liang-Quan Sheng ^a,^*, Hua-Jie Xu ^a, Na-Na Du ^a, Xue-Yue Jiang ^a

PMCID: PMC3006989 PMID: 21587837

Abstract

The title compound, C₁₄H₁₁N₃O₃, adopts an E or trans configuration with respect to the C=N bond. In the molecule there is an intramolecular O—H⋯N hydrogen bond involving the hydroxy substituent at the 2-positon of the naphthalene ring and the adjacent methyleneamino N atom. The molecule is roughly planar, the dihedral angle between the naphthalene and imidazolidine-2,4-dione mean planes being 8.4 (1)°. In the crystal, pairs of N—H⋯O hydrogen bonds link molecules into inversion dimers. These dimers are futher linked via C—H⋯O interactions, forming a three-dimensional network.

Related literature

For the naphthalene group as a fluorophore, see: Li et al. (2010 ▶); Iijima et al. (2010 ▶). For a related structure, see: Xu et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₁N₃O₃
M _r = 269.26
Monoclinic,
a = 11.5122 (7) Å
b = 6.0233 (3) Å
c = 17.9955 (10) Å
β = 96.773 (5)°
V = 1239.13 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.959, T _max = 0.969
4288 measured reflections
2136 independent reflections
1053 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.067
S = 0.72
2136 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020118/su2180sup1.cif

e-66-o1601-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020118/su2180Isup2.hkl

e-66-o1601-Isup2.hkl^{(105.1KB, 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
N3—H3N⋯O1ⁱ	0.890 (18)	1.962 (18)	2.851 (2)	177.9 (19)
O3—H4⋯N1	0.82	1.91	2.622 (2)	145
C6—H6⋯O2ⁱⁱ	0.93	2.55	3.469 (2)	169
C14—H14B⋯O2ⁱⁱ	0.97	2.36	3.038 (2)	127

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

Acknowledgments

This work was supported by the Key Project of Science and Technology of Anhui, (grant No. 08010302218), the Natural Science Foundation of Anhui Provincial University (grant No. KJ2009A127) and the National Natural Science Foundation of China (grant No. 20971024).

supplementary crystallographic information

Comment

The naphthalene group as a fluorophore has been studied extensively due to its characteristic photophysical properties and the competitive stability in the environment (Li et al., 2010; Iijima et al., 2010). As part of an ongoing study of Schiff bases incorporating the naphthalene group (Xu et al., 2009), we report here on the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. It can be seen to display a trans configuration about the C\bN bond. The bond lengths are normal (Allen et al., 1987). There is an intramolecular O-H···N hydrogen bond (Table 1) and the molecule is relatively planar; dihedral angle involving the naphthalene mean plane and the imidazolidine-2,4-dione group mean plane being 8.4 (1)°. In the crystal structure of the title compound N—H···O intermolecular hydrongen bonds (Table 1) link two molecules to form dimmers situated about an inversion center. The molecules are further linked by weak C-H···O interactions to form a three-dimensional network (Fig. 2).

Experimental

The solution of 1-Aminohydantoin hydrochloride (0.151 g, 1 mmol) in 5 ml of ethanol was added slowly to a solution containing 2-hydro-1- naphthaldehyde (0.172 g, 1 mmol) in 15 ml of absolute ethanol under heating and stirring. The mixture was then refluxed for 2 h. Afterwards the mixture was cooled to rt and the resulting solution to stand in air. After 15 days yellow block-shaped crystals were formed, on slow evaporation of the solvent.