4-(4-Nitro­phen­yl)morpholine

Li-Jiao Wang; Wei-Wei Li; Sheng-Yong Yang; Li Yang

doi:10.1107/S1600536812012172

. 2012 Mar 31;68(Pt 4):o1235. doi: 10.1107/S1600536812012172

4-(4-Nitrophenyl)morpholine

Li-Jiao Wang ^a, Wei-Wei Li ^b,^*, Sheng-Yong Yang ^a, Li Yang ^a

PMCID: PMC3344165 PMID: 22606168

Abstract

Aromatic π–π stacking interactions stabilize the crystal structure of the title compound, C₁₀H₁₂N₂O₃, the perpendicular distance between parallel planes being 3.7721 (8) Å. The morpholine ring adopts a chair comformation.

Related literature

For the biological activity and synthesis of 4-(4-nitrophenyl)morpholine derivatives, see: Wang et al. (2010 ▶). For a related structure, see: Yang et al. (2011 ▶). graphic file with name e-68-o1235-scheme1.jpg

Experimental

Crystal data

C₁₀H₁₂N₂O₃
M _r = 208.22
Orthorhombic,
a = 14.5445 (6) Å
b = 8.3832 (3) Å
c = 16.2341 (6) Å
V = 1979.42 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.35 × 0.33 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T _min = 0.992, T _max = 1.000
4949 measured reflections
2023 independent reflections
1377 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.121
S = 1.03
2023 reflections
184 parameters
All H-atom parameters refined
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012172/kj2195sup1.cif

e-68-o1235-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012172/kj2195Isup2.hkl

e-68-o1235-Isup2.hkl^{(99.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012172/kj2195Isup3.cml

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

Acknowledgments

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

supplementary crystallographic information

Comment

4-(4-nitrophenyl)morpholine derivatives are of great importance due to their anticancer activity (Wang et al., 2010;). The title compound is one of the key intermediates in our synthetic investigations of antitumor drugs. We synthesized the title compound and report its crystal structure in this paper.

In the title compound, C₁₀H₁₂N₂O₃, (Fig. 1) the bond lengths and angles are within normal ranges (Yang et al., 2011). Aromatic π–π stacking interactions help to stabilize the crystal structure (Fig. 2). The perpendicular distance between the parallel ring planes is 3.7721 (8) Å, the distance between the centres of gravity Cg—Cg(-x,-y,1 - z) is 3.8499 (11) Å.

Experimental

The title compound was prepared by a method similar to that of Shudong Wang et al. (2010), which Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of dichloromethane.