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

Meng, X.-Z.; Wan, X.-J.

doi:10.1107/S1600536812048489

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 (C-C) = 0.004 Å
Disorder in main residue
R = 0.048
wR = 0.096
Data-to-parameter ratio = 15.5
Details

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

Xiang-Zhen Meng ^a and Xin-Jun Wan ^a ^*

^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-HO 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). For applications of conjugated enynes, see: Ochiai et al. (1999); Saito et al. (2001).

Experimental

Crystal data

C₂₂H₂₃NO₃S
M_r = 381.47
Triclinic, $[P \overline 1]$
a = 9.8186 (10) Å
b = 9.8201 (9) Å
c = 11.3352 (13) Å
= 81.470 (8)°
= 76.308 (9)°
= 75.042 (9)°
V = 1021.46 (18) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.928, T_max = 0.945
9118 measured reflections
4425 independent reflections
3005 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.096
S = 1.00
4425 reflections
285 parameters
170 restraints
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.86	2.32	2.947 (2)	130
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 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.
Ochiai, B., Tomita, I. & Endo, T. (1999). Macromolecules, 32, 238-240.
Saito, S., Kawasaki, T., Tsuboya, N. & Yamamoto, Y. (2001). J. Org. Chem. 66, 796-802.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds