N-(4-Isopropoxyphen­yl)acetamide

Zhang, M.; Lu, R.-Z.; Han, L.-N.; Wei, W.-B.; Wang, H.-B.

doi:10.1107/S1600536809012665

Volume 65
Part 5
Page o1017
May 2009

Received 31 March 2009
Accepted 3 April 2009
Online 10 April 2009

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R = 0.068
wR = 0.202
Data-to-parameter ratio = 16.0
Details

N-(4-Isopropoxyphenyl)acetamide

Min Zhang,^a,^b Ran-Zhe Lu,^a,^b Lu-Na Han,^a,^b Wen-Bin Wei ^a,^b and Hai-Bo Wang ^a ^*

^aCollege of Light Industry and Food Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: wanghaibo@njut.edu.cn

In the molecule of the title compound, C₁₁H₁₅NO₂, the planar acetamide unit [maximum deviation of 0.0014 (6) Å] is oriented at a dihedral angle of 19.68 (4)° with respect to the aromatic ring. An intramolecular C-HO interaction results in the formation of a six-membered ring. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules into chains along the a axis

Related literature

For general background, see: Knesl et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₅NO₂
M_r = 193.24
Orthorhombic, P b c a
a = 9.3010 (19) Å
b = 7.6490 (15) Å
c = 31.394 (6) Å
V = 2233.5 (8) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 294 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.977, T_max = 0.992
2026 measured reflections
2026 independent reflections
1099 reflections with I > 2(I)
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.202
S = 1.01
2026 reflections
127 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N-H0AO2ⁱ	0.86	2.01	2.869 (3)	175
C6-H6AO2	0.93	2.34	2.892 (4)	118
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2659 ).

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-S19.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft. The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Knesl, P., Roeseling, D. & Jordis, U. (2006). Molecules, 11, 286-297.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds