Crystal structure of 4-eth­oxy-N-(4-eth­oxy­phen­yl)-N-phenyl­aniline

Liang-Tao Wu; Ming Kong; Jie-Ying Wu

doi:10.1107/S160053681401900X

. 2014 Aug 30;70(Pt 9):o1077. doi: 10.1107/S160053681401900X

Crystal structure of 4-ethoxy-N-(4-ethoxyphenyl)-N-phenylaniline

Liang-Tao Wu ^a,^b, Ming Kong ^a,^b, Jie-Ying Wu ^a,^b,^*

PMCID: PMC4186099 PMID: 25309234

Abstract

In the title compound, C₂₂H₂₃NO₂, the planes of the ethoxybenzene rings are oriented with respect to that of the phenyl ring at dihedral angles of 61.77 (8) and 84.77 (8)°, and they are twisted with respect to one another, with a dihedral angle of 80.37 (7)°. In the crystal, weak C—H⋯π interactions link the molecules into supramolecular chains propagating along [101].

Keywords: crystal structure, triphenylamine derivatives, supramolecular chains, C—H⋯π interactions

Related literature

For applications of triphenylamine derivatives, see: Liu et al. (2012 ▶); Pina et al. (2013 ▶). For related compounds, see: Wang et al. (2011 ▶); Gudeika et al.(2012 ▶). For properties of triphenyl derivatives, see: Costa & Santos (2013 ▶); Metri et al. (2012 ▶). graphic file with name e-70-o1077-scheme1.jpg

Experimental

Crystal data

C₂₂H₂₃NO₂
M _r = 333.41
Monoclinic,
a = 7.3634 (7) Å
b = 31.908 (3) Å
c = 8.1372 (8) Å
β = 107.598 (1)°
V = 1822.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
13155 measured reflections
3274 independent reflections
2288 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.106
S = 1.03
3274 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S160053681401900X/xu5812sup1.cif

e-70-o1077-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401900X/xu5812Isup2.hkl

e-70-o1077-Isup2.hkl^{(157.4KB, hkl)}

Click here for additional data file.^{(6.8KB, cml)}

Supporting information file. DOI: 10.1107/S160053681401900X/xu5812Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S160053681401900X/xu5812fig1.tif

The molecular structure of the title compound showing 30% probability displacement ellipsoids.

Click here for additional data file.^{(2.8MB, tif)}

. DOI: 10.1107/S160053681401900X/xu5812fig2.tif

The weak interactions among molecules.

CCDC reference: 1016997

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cg1ⁱ	0.96	2.83	3.6763 (17)	148

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Symmetry code: (i) Inline graphic .

Acknowledgments

The work was supported by the National Natural Science Foundation of China (grant Nos. 21271004 and 51372003) and the Natural Science Foundation of Anhui Province, China (grant No. 1208085MB22).

supplementary crystallographic information

S1. Comment

Tripheylamine derivatives catch considerable interest and attention in application of OLEDs and efficient optical chemosensors due to useful properties in electrical conductivity and electroluminescence (Pina et al., 2013; Liu et al., 2012). Much effort has been made to explore the relationship between their structures and properties. The ethoxyl groups as donors in the title compound have enhanced the properties in several optical applications, its special structure also contributes to its transport properties when used to those areas (Costa & Santos, 2013 and Metri et al., 2012). In the molecule, the two ethoxybenzene rings are oriented with respect to the phenyl ring at 61.77 (8) and 84.77 (8)°, and they are twisted to each other with a dihedral angle of 80.37 (7)°. In the crystal, weak C—H···π interaction links the molecules into the supramolecular chains propagated along the [101] direction.

S2. Experimental

A mixture of 4-iodophenol and sodium hydroxide was grinded for 0.5 h and added to 1000 ml flask, following the addition of bromoethane (750 ml) as solvent, Cs₂CO₃ (4 g) and 18-crown-6 (1 g, 3.78 mmol) as catalysts. The mixture was refluxed for 72 h, and obtained yellow oil was washed with NaOH solution (500 ml, 5%) until neutral. After extraction with dichloromethane (50 ml) for three times, the organic solution was evaporated, which yielded the intermediate as a white product (101 g, 90.5%). A 1,2-dichlorobenzene (purified) solution containing synthesized 4-ethoxy-iodobenzene (20.86 g, 75 mmol), aniline (2.38 g, 22 mmol), K₂CO₃ (17.94 g, 130 mmol), Cu powder (8.34 g, 130 mmol), 18-crown-6 (100 mg, 0.38 mmol) was stirred under N₂ for 0.5 h at room temperature, refluxed for 2 h, and continuous reaction at air. After cooling, copper was filtered out, 1,2-dichlorobenzene was evaporated, then white solid was obtained through column chromatography purification. 1H NMR: (400 MHz, (C₁D₃₎2_C1_O1), d(p.p.m.): d(p.p.m.): 7.18–7.14 (t, 2H), 7.02–7.00 (d, 4H), 6.86–6.71 (m, 7H), 4.04–3.99 (m, 4H), 1.37–1.34 (t, 6H).