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Volume 69 
Part 9 
Page o1479  
September 2013  

Received 26 July 2013
Accepted 17 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.100
Data-to-parameter ratio = 22.6
Details
Open access

(E,Z)-1-(4-Chlorophenyl)-5-phenyl-5-(phenylsulfanyl)penta-2,4-dien-1-one

aNesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 119991 Moscow, Russian Federation, and bDepartment of Chemical and Chemical Technology, Togliatti State University, 445667 Togliatti, Russian Federation
Correspondence e-mail: vologzhanina@mail.ru

The penta-2,4-dien-1-one fragment of the title compound, C23H17ClOS, is twisted by 20.0 (3)°, as measured by the dihedral angle between the planes of the carbonyl group and its attached C atom and the distant C=C double bond and its attached C atom. The 4-chlorophenyl group forms a dihedral angle of 4.0 (3)° with the adjacent carbonyl group. Conjugation between the phenyl ring and the C=C double bond is absent; the dihedral angle between the phenyl ring and the C-C=C fragment is 34.3 (2)°. In the crystal, molecules are linked via C-H...O hydrogen bonds, forming chains parallel to the b-axis direction.

Related literature

For the biological activity of chalcones, and their arylthio-containing derivatives, see: Chate et al. (2012[Chate, A. V., Joshi, R. S., Mandhane, P. G., Mohekar, S. R. & Gill, C. H. (2012). Phosphorus Sulfur Silicon Relat. Elem. 187, 327-335.]); Nielsen et al. (2005[Nielsen, S. F., Larsen, M., Boesen, T., Schonning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667-2677.]); Wu et al. (2011[Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.]), Karaman et al. (2012[Karaman, I., Gezegen, H., Ceylan, M. & Dilmac, M. (2012). Phosphorus Sulfur Silicon Relat. Elem. 187, 580-586.]). For the synthesis and crystal structures of precursor 1,5-diarylpent-2-en-4-yn-1-ones, see: Golovanov et al. (2013[Golovanov, A. A., Latypova, D. R., Bekin, V. V., Pisareva, V. S., Vologzhanina, A. V. & Dokichev, V. A. (2013). Russ. J. Org. Chem. 49. In the press.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C23H17ClOS

  • Mr = 376.88

  • Orthorhombic, P b c a

  • a = 8.2663 (11) Å

  • b = 11.1661 (13) Å

  • c = 39.478 (6) Å

  • V = 3643.9 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.33 mm-1

  • T = 120 K

  • 0.38 × 0.08 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.903, Tmax = 0.967

  • 20709 measured reflections

  • 5311 independent reflections

  • 3104 reflections with I > 2[sigma](I)

  • Rint = 0.088

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.100

  • S = 1.00

  • 5311 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7A...O1i 0.95 2.57 3.515 (3) 178
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 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: LD2112 ).


References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chate, A. V., Joshi, R. S., Mandhane, P. G., Mohekar, S. R. & Gill, C. H. (2012). Phosphorus Sulfur Silicon Relat. Elem. 187, 327-335.  [CrossRef] [ChemPort]
Golovanov, A. A., Latypova, D. R., Bekin, V. V., Pisareva, V. S., Vologzhanina, A. V. & Dokichev, V. A. (2013). Russ. J. Org. Chem. 49. In the press.
Karaman, I., Gezegen, H., Ceylan, M. & Dilmac, M. (2012). Phosphorus Sulfur Silicon Relat. Elem. 187, 580-586.  [CrossRef] [ChemPort]
Nielsen, S. F., Larsen, M., Boesen, T., Schonning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667-2677.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1479  [ doi:10.1107/S160053681302312X ]

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