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Volume 69 
Part 9 
Page o1405  
September 2013  

Received 22 July 2013
Accepted 6 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.138
Data-to-parameter ratio = 13.4
Details
Open access

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

aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China
Correspondence e-mail: jywu1957@163.com

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[Wan, C.-Q. & Mak, T. C. W. (2011). Cryst. Growth Des. 11, 832-842.]). For related compounds, see: Encinas (2002[Encinas, S. (2002). Chem. Eur. J. 8, 137-150.]); Feng et al. (2012[Feng, Q.-Y., Lu, X.-F., Zhou, G. & Wang, Z.-S. (2012). Phys. Chem. Chem. Phys. 14, 7993-7999.]).

[Scheme 1]

Experimental

Crystal data
  • C24H18N2OS

  • Mr = 382.46

  • Monoclinic, P 21 /c

  • a = 10.976 (5) Å

  • b = 18.029 (5) Å

  • c = 9.697 (5) Å

  • [beta] = 90.728 (5)°

  • V = 1918.7 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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 > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.138

  • S = 0.95

  • 3388 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

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
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+2.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5725 ).


Acknowledgements

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).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Encinas, S. (2002). Chem. Eur. J. 8, 137-150.  [CSD] [CrossRef] [PubMed] [ChemPort]
Feng, Q.-Y., Lu, X.-F., Zhou, G. & Wang, Z.-S. (2012). Phys. Chem. Chem. Phys. 14, 7993-7999.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wan, C.-Q. & Mak, T. C. W. (2011). Cryst. Growth Des. 11, 832-842.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1405  [ doi:10.1107/S1600536813021946 ]

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