4-(4-Nitro­styr­yl)-N,N-diphenyl­aniline

Zhi-Wen Zhang; Yan-Qiu Liu; Yu-Chao Zhu; Jie-Ying Wu

doi:10.1107/S1600536812023719

. 2012 May 31;68(Pt 6):o1933. doi: 10.1107/S1600536812023719

4-(4-Nitrostyryl)-N,N-diphenylaniline

Zhi-Wen Zhang ^a, Yan-Qiu Liu ^a, Yu-Chao Zhu ^a, Jie-Ying Wu ^a,^*

PMCID: PMC3379487 PMID: 22719685

Abstract

In the triarylamine group of the title compound, C₂₆H₂₀N₂O₂, the N atom adopts an approximately trigonal–planar geometry, lying 0.046 (5) Å from the plane P defined by its three neighbouring C atoms; the benzene and two terminal phenyl rings are twisted by 37.4 (1), 31.4 (1) and 47.8 (1)°, respectively from plane P. In the trans-stilbene fragment, the two benzene rings form a dihedral angle of 31.3 (1)°. In the crystal, weak intermolecular C—H⋯O interactions link the molecules into ribbons in [100].

Related literature

For a related structure, see: Yang et al. (2003 ▶). For background to push–pull chromophores, see: Marder et al. (1991 ▶); Reinhardt et al. (1998 ▶). graphic file with name e-68-o1933-scheme1.jpg

Experimental

Crystal data

C₂₆H₂₀N₂O₂
M _r = 392.44
Monoclinic,
a = 8.4884 (3) Å
b = 8.9834 (3) Å
c = 27.0880 (8) Å
β = 96.500 (2)°
V = 2052.31 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.976, T _max = 0.984
7675 measured reflections
3606 independent reflections
2213 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.185
S = 1.04
3606 reflections
272 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023719/cv5302sup1.cif

e-68-o1933-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023719/cv5302Isup2.hkl

e-68-o1933-Isup2.hkl^{(176.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812023719/cv5302Isup3.cml

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
C15—H15⋯O1ⁱ	0.93	2.58	3.481 (4)	162
C12—H12⋯O2ⁱⁱ	0.93	2.56	3.308 (4)	138

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant Nos. 21071001 and 51142011), the Education Committee of Anhui Province (grant No. KJ2010A030) and the Natural Science Foundation of Anhui University (grant No. yqh100053).

supplementary crystallographic information

Comment

Push-pull chromophores are characterized by the conjugated linkage of an electron-donating group (D) and an electron-accepting group (A). Such molecules are potentially useful for nonlinear optical applications and many D-π-A type chromophores have been reported (Marder et al., 1991; Reinhardt et al., 1998). As a part of an ongoing study of such type chromophores, here we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related 4-(4-methoxystyryl)-N,N-diphenylaniline (Yang et al., 2003). The C = C double bond ( = 1.276 (4) Å) in the molecule adopts a trans-configuration. The dihedral angle between the benzene ring of the triarylamine group and another benzene ring linked by double bond is 31.34 (13) °. In the crystal, weak intermolecular C—H···O interactions (Table 1) link the molecules into ribbons in [100].

Experimental

2.73 g (10 mmol) of diethyl(4-nitrophenyl)methylphosphonate were put into a dry mortar, then 2.24 g (20 mmol) t-BuOK were placed into powder, a modicum of 18-crown-6 and 2.72 g (10 mmol) 4-(diphenylamino)benzaldehyde were adde and vigorously grinded. The mixture was monitored by TLC. After completion of the reaction the mixture was dissolved in 150 ml CH₂Cl₂ and washed with Di-water, the organic layer separated and dried over MgSO₄,filterd and solvent removed in vacuo. The product was recrystallized from anhydrous ethanol, to give 2.12 g red acicular crystal. Yield, 54.1%. 1H NMR: (400 Hz, CDCl₃), d(p.p.m.): 8.20(d, 2H, J = 8.4 Hz) 7.60(d, 2H, J=8.8 Hz) 7.40(d, 2H, J=8.8 Hz) 7.30–7.26(m, 4H) 7.19(s, 1H) 7.13(d, 4H, J=8.0) 7.09–7.03(m, 4H) 6.99(s, 1H) 13 C NMR (125 MHz, CDCl₃) d (p.p.m.) 148.7, 147.8, 147.4, 146.5, 145.0, 144.5, 133.5, 133.0, 130.0 129.7, 129.5, 129.4, 128.2, 126.7, 126.5, 125.1, 124.8, 124.3, 123.8 123.6, 122.8, 122.3. IR (KBr, cm^-1): 3029 1585 1514 1485 1335 1283 1175 1111 970 841 758 694. MS: m/z (%) = 504.20 (100)