(E)-3-[5-(Di­phenyl­amino)­thio­phen-2-yl]-1-(pyridin-3-yl)prop-2-en-1-one

Rui Li; Dan-Dan Li; Jie-Ying Wu

doi:10.1107/S1600536813021946

. 2013 Aug 10;69(Pt 9):o1405. doi: 10.1107/S1600536813021946

(E)-3-[5-(Diphenylamino)thiophen-2-yl]-1-(pyridin-3-yl)prop-2-en-1-one

Rui Li ^a, Dan-Dan Li ^a, Jie-Ying Wu ^a,^*

PMCID: PMC3884491 PMID: 24427043

Abstract

In the title compound, C₂₄H₁₈N₂OS, the pyridine and the two phenyl rings are oriented at dihedral angles of 10.1 (5), 71.7 (6) and 68.7 (5)°, respectively, to the central thiophene ring. In the crystal, pairs of weak C—H⋯O hydrogen bonds link inversion-related molecules, forming dimers. The dimers are linked by further weak C—H⋯O hydrogen bonds, forming chains running along the a-axis direction.

Related literature

For background to the title compound, see: Wan & Mak (2011 ▶). For related compounds, see: Encinas (2002 ▶); Feng et al. (2012 ▶). graphic file with name e-69-o1405-scheme1.jpg

Experimental

Crystal data

C₂₄H₁₈N₂OS
M _r = 382.46
Monoclinic,
a = 10.976 (5) Å
b = 18.029 (5) Å
c = 9.697 (5) Å
β = 90.728 (5)°
V = 1918.7 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
13536 measured reflections
3388 independent reflections
2517 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.138
S = 0.95
3388 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (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/S1600536813021946/xu5725sup1.cif

e-69-o1405-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021946/xu5725Isup2.hkl

e-69-o1405-Isup2.hkl^{(166.2KB, hkl)}

Click here for additional data file.^{(7.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813021946/xu5725Isup3.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
C11—H11⋯O1ⁱ	0.93	2.54	3.410 (3)	155
C12—H12⋯O1ⁱⁱ	0.93	2.43	3.346 (3)	166

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 21071001), the Foundation of the Education Committee of Anhui Province (grant No. KJ2010A030) and the Natural Science Foundation of Anhui Province (grant No. 1208085MB22).

supplementary crystallographic information

1. Comment

Carbonyl group widely exists in organic and biological systems and plays a crucial role in stabilizing both the extended crystal structures of small molecules and biological systems through various weak intermolecular interactions generated via carbonyl group (Wan & Mak, 2011). Besides, the introduction about the highpolarizability of sulfur atoms in thiophene rings leads to a stabilization of the conjugated chain and to excellent charge transport properties, which are one of the most crucial assets for applications in organic and molecular electronics (Encinas, 2002; Feng et al., 2012).

The crystal structure of the title compound, exists in an E configuration with respect to the C17=C18 ethenyl bond (1.332 (3) Å), as indicated by the torsion angle C16—C17—C18—C19 = 177.90 (1) °. The prop-2-en-1-one unit (C17—C19/O1) is nearly planar and the torsion angle O1—C17—C18—C19 is 8.2 (3) °. The Carbonyl bridge is nearly planar to the pyridyl ring and the thiophene ring make the dihedral angles of 7.22 (7)° and 7.07 (8)°, respectively (Fig.1). In the terminal phenyl rings region of the molecule, each phenyl group makes dihedral angles of 71.7 (6)° and 68.7 (5)° with the thiophene ring.

2. Experimental

The title compound was synthesized by mixing 3-acetylpyridine (1.21 g, 10 mmol) with 5-(diphenylamino)thiophene-2-carbaldehyde (2.79 g, 10 mmol) in methanol (25 ml) in the presence of 20% NaOH (aq) (5 ml). The mixture was stirred at room temperature for 12 h. The red solid formed was filtered and washed with distilled water, dried over vacuum. 1H NMR: (400 Hz, DMSO-d⁶), d(p.p.m.): 9.05 (d, 1H), 8.48 (d, 1H), 8.25 (d, 1H), 8.12 (d, 1H), 7.86 (d, 1H), 7.64 (m, 1H), 7.55 (t, 4H), 7.40 (d, 1H), 7.32 (d, 4H),7.29 (t, 2H), 6.65 (d, 1H)