Bis[4-(3-amino­phen­oxy)phen­yl] ketone

Yang Wang; Xin-yi Zhu; Xiao-yan Ma; Guo-wei Gao; Jian Men

doi:10.1107/S1600536809025951

. 2009 Jul 11;65(Pt 8):o1823. doi: 10.1107/S1600536809025951

Bis[4-(3-aminophenoxy)phenyl] ketone

Yang Wang ^a, Xin-yi Zhu ^a, Xiao-yan Ma ^b, Guo-wei Gao ^a, Jian Men ^a,^*

PMCID: PMC2977108 PMID: 21583525

Abstract

In the molecule of the title compound, C₂₅H₂₀N₂O₃, the dihedral angles formed by adjacent benzene rings are 66.75 (8), 48.37 (8) and 71.43 (9)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the properties and synthesis of the title compound, see: Wilson et al. (1990 ▶); Mehdipour-Ataei & Saidi (2008 ▶). For the applications of the title compound, see: Rao & Prabhakaran (1992 ▶).

Experimental

Crystal data

C₂₅H₂₀N₂O₃
M _r = 396.43
Triclinic,
a = 7.370 (3) Å
b = 11.856 (3) Å
c = 12.319 (3) Å
α = 101.79 (4)°
β = 95.10 (4)°
γ = 107.86 (3)°
V = 989.6 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 K
0.48 × 0.42 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3693 measured reflections
3682 independent reflections
2206 reflections with I > 2σ(I)
R _int = 0.006
3 standard reflections every 200 reflections intensity decay: 1.5%

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.165
S = 1.05
3682 reflections
288 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025951/rz2344sup1.cif

e-65-o1823-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025951/rz2344Isup2.hkl

e-65-o1823-Isup2.hkl^{(180.5KB, 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
N1—H1N1⋯O1ⁱ	0.92 (4)	2.32 (4)	3.223 (5)	164 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Undergraduates’ Innovative Experiment Project of Sichuan University and thank Mr Zhi-Hua Mao of Sichuan University for the X-Ray data collection.

supplementary crystallographic information

Comment

Aromatic polyimides has found useful applications in aircraft technology, space vehicles, sea transport equipment and other applications due to their excellent thermal stability, good mechanical properties, low dielectric constants and intrinsic purity (Wilson et al., 1990). The title compound is an important raw material for the synthesis of aromatic polyimides, as the presence of ether and ketone groups connected by aromatic rings greatly improves the chain flexibility (Rao & Prabhakaran, 1992; Mehdipour-Ataei & Saidi, 2008). Herein, we report the synthesis and crystal structure of the title compound.

The structure of the title compound (Fig. 1) is not planar. The dihedral angle between the two central benzene rings, ring A (C7–C12) and ring B (C14–C19), is 48.37 (8)°. Ring A forms a dihedral angle of 66.75 (8)° with the C1–C6 benzene ring. The corresponding dihedral angle between ring B and the C20–C25 benzene ring is 71.43 (9)°. The plane formed by atoms C10, C14, O1 and C13, makes a dihedral angle of 22.28 (12)° and 31.23 (8)° with ring A and B, respectively. The crystal structure is stabilized by N—H···O hydrogen bonds (Table 1) linking centrosymmetrically related molecules into dimers.

Experimental

4,4'-Difluorobenzophenone (11.0 g, 0.05 mol), m-aminophenol (22.0 g, 0.20 mol) and anhydrous potassium carbonate (14.0 g, 0.10 mol) were dissolved in a solution of toluene (60 ml) and N,N-dimethylformamide (100 ml) in a three-necked flask. The mixture was heated to reflux and water was removed by azeotropic distillation. After complete dehydration, the mixture was poured to a large excess of ice water. Then, the precipitated solid was collected by filtration and recrystallized from ethanol to obtain a tan solid (16.5 g, 76% yield, m.p.411–413 K). Red single crystals suitable for X-ray diffraction were obtained by slow evaporation at room temperature of a toluene solution.