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Volume 69 
Part 1 
Page o78  
January 2013  

Received 22 November 2012
Accepted 26 November 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.048
wR = 0.096
Data-to-parameter ratio = 15.5
Details
Open access

(E)-2-Phenyl-N-tosylnon-2-en-4-ynamide

aDepartment of Chemistry and Life Science, Chaohu College, Anhui Province, People's Republic of China
Correspondence e-mail: wzys2012@126.com

The molecule of the title compound, C22H23NO3S, adopts an E conformation about the C=C bond. The dihedral angle between the benzene rings is 23.79 (5)°. In the crystal, pairs of N-H...O hydrogen bonds link the molecules, forming inversion dimers. The terminal butyl group is disordered over two sets of sites in a 0.559 (6):0.441 (6) ratio.

Related literature

For the synthesis of the titlw compound, see: Cheng et al. (2012[Cheng, D., Ling, F., Li, Z.-X., Yao, W.-J. & Ma, C. (2012). Org. Lett. 14, 3146-3149.]). For applications of conjugated enynes, see: Ochiai et al. (1999[Ochiai, B., Tomita, I. & Endo, T. (1999). Macromolecules, 32, 238-240.]); Saito et al. (2001[Saito, S., Kawasaki, T., Tsuboya, N. & Yamamoto, Y. (2001). J. Org. Chem. 66, 796-802.]).

[Scheme 1]

Experimental

Crystal data
  • C22H23NO3S

  • Mr = 381.47

  • Triclinic, [P \overline 1]

  • a = 9.8186 (10) Å

  • b = 9.8201 (9) Å

  • c = 11.3352 (13) Å

  • [alpha] = 81.470 (8)°

  • [beta] = 76.308 (9)°

  • [gamma] = 75.042 (9)°

  • V = 1021.46 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 293 K

  • 0.42 × 0.38 × 0.32 mm

Data collection
  • Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.928, Tmax = 0.945

  • 9118 measured reflections

  • 4425 independent reflections

  • 3005 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.096

  • S = 1.00

  • 4425 reflections

  • 285 parameters

  • 170 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 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
N1-H1...O2i 0.86 2.32 2.947 (2) 130
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XU5655 ).


Acknowledgements

The work was supported financially by the Chaohu College Project (XLY-201105).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Cheng, D., Ling, F., Li, Z.-X., Yao, W.-J. & Ma, C. (2012). Org. Lett. 14, 3146-3149.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Ochiai, B., Tomita, I. & Endo, T. (1999). Macromolecules, 32, 238-240.  [ISI] [CrossRef] [ChemPort]
Saito, S., Kawasaki, T., Tsuboya, N. & Yamamoto, Y. (2001). J. Org. Chem. 66, 796-802.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o78  [ doi:10.1107/S1600536812048489 ]

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