4-[3-(4-Nitro­phen­oxy)prop­oxy]aniline

Li-Mei Zheng; Xian Wei; Xiao-Rong Peng; Jin-Ping Zeng; Yun-Qian Zhang

doi:10.1107/S1600536808032406

. 2008 Oct 15;64(Pt 11):o2110. doi: 10.1107/S1600536808032406

4-[3-(4-Nitrophenoxy)propoxy]aniline

Li-Mei Zheng ^a, Xian Wei ^b, Xiao-Rong Peng ^b, Jin-Ping Zeng ^b, Yun-Qian Zhang ^b,^*

PMCID: PMC2959529 PMID: 21580974

Abstract

The molecules of the title compound, C₁₅H₁₆N₂O₄, are linked via N—H⋯O hydrogen bonds, forming undulating one-dimensional chains. Adjacent chains are linked by weak C—H⋯π interactions, forming a three-dimensional network.

Related literature

For general background, see: Day & Arnold (2000 ▶); Day et al. (2002 ▶); Freeman et al. (1981 ▶); Kim et al. (2000 ▶).

Experimental

Crystal data

C₁₅H₁₆N₂O₄
M _r = 288.30
Orthorhombic,
a = 10.808 (8) Å
b = 34.79 (3) Å
c = 7.596 (6) Å
V = 2857 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.23 × 0.19 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.978, T _max = 0.984
17736 measured reflections
2509 independent reflections
1554 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.126
S = 1.05
2509 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032406/at2638sup1.cif

e-64-o2110-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032406/at2638Isup2.hkl

e-64-o2110-Isup2.hkl^{(120.8KB, 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—H2B⋯O1ⁱ	0.86	2.29	3.123 (3)	164
C3—H3⋯Cg1ⁱⁱ	0.93	3.07	3.513 (4)	111
C7—H7B⋯Cg2ⁱⁱⁱ	0.97	2.71	3.567 (4)	148
C13—H13⋯Cg2^iv	0.93	3.01	3.757 (4)	139

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 phenyl rings, respectively

Acknowledgments

We acknowledge the support of the National Natural Science Foundation of China (No. 20662003) and the Foundation of the Governor of Guizhou Province, China.

supplementary crystallographic information

Comment

As part of our ongoing investigation on bibenzene compound, we present the crystal structure of the title compound (I) containing multiple functional groups that can develop strong interactions with cucurbit[n]urils (CB[n]) (Freeman et al., 1981; Day & Arnold, 2000; Day et al., 2002; Kim et al., 2000)

The crystal structure of (I) is shown in Fig.1. Two phenyl rings were linked by ethereal chain forming a non-coplanar structure and the dihedral angle between two phenyl ring is 26.13 (9) Å. Molecules are linked via N2—H2B···O1 hydrogen bonds forming a undulant one-dimensional chains (Fig. 2) and adjacent chains are linked by C—H···π interaction forming a three-dimensional framework (Table 1, Cg1 and Cg2 are centroids of the phenyl ring (C1—C6) and (C10—C15), respectively).

Experimental

P-toluenesulfonyl chloride (7.62 g, 40 mmol) was added slowly, whilst stirring, to a pyridine solution (50 ml) containing 1,3-propanediol (1.52 g, 20 mmol). The mixture was stirred for about 4 h in the range of 268 K - 278 K. Water (40 ml) was added to the resulting solution, the precipitate was collected by filtration, the solid product was crystallized using ethanol. The solid product (6.85 g, 20 mmol) dissolved in DMF (100 ml) containing K₂CO₃ (2 g), p-nitrophenol (0.54 g, 4 mmol) was added slowly, to the DMF(100 ml) solution, and the mixture was heated at 353 K for 24 h, and then the solvent was removed into water and filtered, the residue was washed with water, and 1,3-bis(-nitrylphenoxy)-propane was obtained. Hydrazine (30 g,80%) was added slowly to a stirred solution of ethanol (50 ml) containing 1,4-bis(-nitrylphenoxy)-propane (3.12 g, 10 mmol), FeCl₃.6H₂O (0.8 g) and active carbon (1.8 g) at 348 K for 5 h, and then the solvent was filtered, the solid product was crystallized using ethanol, Single crystals of (I) were obtained after a week.