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Volume 69 
Part 6 
Page o911  
June 2013  

Received 4 May 2013
Accepted 13 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.107
Data-to-parameter ratio = 21.9
Details
Open access

(E)-1,5-Diphenylpent-2-en-4-yn-1-one

aDepartment of Chemistry and Chemical Technology, Togliatti State University, 14 Belorusskaya St, Togliatti 445667, Russian Federation, and bX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: a.s.bunev@gmail.com

The title compound, C17H12O, has an E conformation about the C=C bond. The C-C[triple bond]C-C torsion angle is 7.7 (2)°, and the mean planes of the phenylethylenone [r.m.s. deviation = 0.059 (1) Å] and phenylacetylene [r.m.s. deviation = 0.023 (1) Å] fragments form a dihedral angle of 14.16 (7)°. In the crystal, weak C-H...O interactions link the molecules into zigzag chains propagated in [010].

Related literature

For the synthesis and properties of enynones, see: Toshima et al. (1999[Toshima, H., Aramaki, H. & Ichihara, A. (1999). Tetrahedron Lett. 40, 3587-3590.]); Ohe et al. (2002[Ohe, K., Yokoi, T., Miki, K. & Uemura, S. (2002). J. Am. Chem. Soc. 124, 526-527.]); Miki et al. (2002[Miki, K., Nishino, F., Ohe, K. & Uemura, S. (2002). J. Am. Chem. Soc. 124, 5260-5261.]); Kuroda et al. (2004[Kuroda, H., Hanaki, E., Izawa, H., Kano, M. & Itahashi, H. (2004). Tetrahedron, 60, 1913-1920.]); Casey & Strotman (2005[Casey, C. P. & Strotman, N. A. (2005). J. Org. Chem. 70, 2576-2581.]). For the crystal structures of related compounds, see: König et al. (1995[König, B., Bubenitschek, P. & Jones, P. G. (1995). Liebigs Ann. pp. 195-198.]); Chen & Liu (2008[Chen, J. & Liu, Y. (2008). Tetrahedron Lett. 49, 6655-6658.]); Lu et al. (2009[Lu, Y., Du, X., Jia, X. & Liu, Y. (2009). Adv. Synth. Catal. 351, 1517-1522.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12O

  • Mr = 232.27

  • Orthorhombic, P 21 21 21

  • a = 5.4696 (4) Å

  • b = 13.7164 (10) Å

  • c = 16.3117 (11) Å

  • V = 1223.76 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 120 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.977, Tmax = 0.985

  • 15765 measured reflections

  • 3576 independent reflections

  • 2987 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.107

  • S = 1.07

  • 3576 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16...O1i 0.95 2.54 3.165 (2) 124
C17-H17...O1i 0.95 2.61 3.202 (2) 121
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). 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: CV5408 ).


Acknowledgements

The authors are grateful to the Ministry of Education and Science of the Russian Federation (State program No. 3.1168.2011).

References

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Casey, C. P. & Strotman, N. A. (2005). J. Org. Chem. 70, 2576-2581.  [CrossRef] [PubMed] [ChemPort]
Chen, J. & Liu, Y. (2008). Tetrahedron Lett. 49, 6655-6658.  [ISI] [CSD] [CrossRef] [ChemPort]
König, B., Bubenitschek, P. & Jones, P. G. (1995). Liebigs Ann. pp. 195-198.
Kuroda, H., Hanaki, E., Izawa, H., Kano, M. & Itahashi, H. (2004). Tetrahedron, 60, 1913-1920.  [ISI] [CrossRef] [ChemPort]
Lu, Y., Du, X., Jia, X. & Liu, Y. (2009). Adv. Synth. Catal. 351, 1517-1522.  [CSD] [CrossRef] [ChemPort]
Miki, K., Nishino, F., Ohe, K. & Uemura, S. (2002). J. Am. Chem. Soc. 124, 5260-5261.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ohe, K., Yokoi, T., Miki, K. & Uemura, S. (2002). J. Am. Chem. Soc. 124, 526-527.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Toshima, H., Aramaki, H. & Ichihara, A. (1999). Tetrahedron Lett. 40, 3587-3590.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o911  [ doi:10.1107/S1600536813013044 ]

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