(E)-3-[(2-Hy­droxy­naphthalen-1-yl)methyl­idene­amino]-5-(morpholin-4-yl­meth­yl)-1,3-oxazolidin-2-one

Na-Na Du; Hua-Jie Xu; Chong-Fu Song; Liang-Quan Sheng

doi:10.1107/S1600536811020368

. 2011 Jun 18;67(Pt 7):o1740. doi: 10.1107/S1600536811020368

(E)-3-[(2-Hydroxynaphthalen-1-yl)methylideneamino]-5-(morpholin-4-ylmethyl)-1,3-oxazolidin-2-one

Na-Na Du ^a, Hua-Jie Xu ^a, Chong-Fu Song ^a, Liang-Quan Sheng ^a,^*

PMCID: PMC3151765 PMID: 21837128

Abstract

The title compound, C₁₉H₂₁N₃O₄, crystallizes with two independent molecules in the asymmetric unit. In both molecules, there is an intramolecular O—H⋯N hydrogen bond, which correlates with the fact that each molecule adopts an E configuration with respect to the C=N bond. In the crystal, there are C—H⋯O and C—H⋯π interactions present.

Related literature

For background to the naphthalene group as a fluorophore, see: Li et al. (2010 ▶); Iijima et al. (2010 ▶). For related structures, see: Xu et al. (2009 ▶); Liu et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₉H₂₁N₃O₄
M _r = 355.39
Monoclinic,
a = 10.7764 (6) Å
b = 12.0953 (8) Å
c = 26.7606 (14) Å
β = 93.452 (5)°
V = 3481.7 (4) Å³
Z = 8
Cu Kα radiation
μ = 0.79 mm⁻¹
T = 291 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.797, T _max = 0.857
15194 measured reflections
6408 independent reflections
4362 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.142
S = 1.03
6408 reflections
469 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.18 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 datablock(s) global, I. DOI: 10.1107/S1600536811020368/su2276sup1.cif

e-67-o1740-sup1.cif^{(33.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020368/su2276Isup2.hkl

e-67-o1740-Isup2.hkl^{(307.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020368/su2276Isup3.cml

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

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

Cg3 is the centroid of the C10–C14/C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N3	0.82	1.82	2.535 (3)	145
O8—H8⋯N6	0.82	1.84	2.549 (2)	144
C3—H3B⋯O2	0.97	2.49	3.141 (3)	124
C9—H9⋯O7	0.93	2.54	3.472 (3)	177
C18—H18⋯O7	0.93	2.57	3.500 (3)	174
C26—H26A⋯O3ⁱ	0.97	2.49	3.403 (3)	157
C36—H36⋯O5ⁱⁱ	0.93	2.48	3.371 (3)	161
C23—H23B⋯Cg3ⁱⁱⁱ	0.97	2.65	3.589 (2)	162

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

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 such compounds based on the naphthalene group (Xu et al., 2009; Liu et al., 2011), we report herein on the crystal structure of the title compound.

The molecular structure of the two independent molecules (A and B) of the title compound is shown in Fig. 1. Both molecules display a trans configuration about the C═N bond. The bond distances are within the normal range (Allen et al., 1987). In each molecule there is an intramolecular N-H···O hydrogen bond (Table 1), graph set S(5) (Bernstein et al., 1995), and the oxazolidine rings have chair conformations.

In the crystal molecules are linked via C-H···O and C-H···π interactions (Table 1).

Experimental

A solution of 3-amino-5-(morpholinomethyl)oxazolidin-2-one (0.10 g, 0.5 mmol) in 5 ml of ethanol was added slowly to a solution of 2-hydro-1- naphthaldehyde (0.086 g,1 mmol) in 10 ml of absolute ethanol under heating and stirring. The mixture was then refluxed for 2 h. The mixture was then cooled to room temperature and the resulting solution was left to stand in air for 15 days. Colourless needle-shaped crystals of the title compound were formed, on slow evaporation of the solvent.