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Volume 69 
Part 11 
Page o1715  
November 2013  

Received 9 October 2013
Accepted 23 October 2013
Online 26 October 2013

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.132
Data-to-parameter ratio = 18.4
Details
Open access

2-Isopropyl-4-meth­oxy-5-methyl­phenyl acetate

aLaboratoire de Synthése Organique et Physico-Chimie Moléculaire, Faculté des Sciences-Semlalia, Université Cadi Ayyad, BP 2390, 40001, Marrakech, Morocco,bLaboratoire de Matériaux et Cristallochimie, Faculté des Sciences de Tunis, Université de Tunis ElManar, 2092 ElManar II, Tunis, Tunisia, and cEquipe de Chimie des Matériaux et de l'Environnement, FSTG-Marrakech, Université Cadi Ayyad, Bd Abdelkrim Khattabi, BP 549, Marrakech, Morocco
Correspondence e-mail: eh_soumhi@yahoo.fr

In the title compound, C13H18O3, the benzene ring is almost perpendicular to the acet­oxy plane, making a dihedral angle of 89.33 (11)°. In the crystal, mol­ecules are linked by weak C-H...O hydrogen bonds, forming a zigzag chain along the c-axis direction.

Related literature

For background to natural monoterpenic phenols and their derivatives, see: Yuan-Lang & Erdtman (1962[Yuan-Lang, C. & Erdtman, H. (1962). Acta Chem. Scand. 16, 1291-1295.]); Ündeger et al. (2009[Ündeger, Ü., Basaran, A., Degen, G. H. & Basaran, N. (2009). Food Chem. Toxicol. 47, 2037-2043.]); Osorio et al. (2006[Osorio, E., Arango, G., Robledo, S., Muñoz, D., Jaramillo, L. & Vélez, I. (2006). Acta Farm. Bonaer. 25, 405-413.]). For a related structure, see: Rajouani et al. (2008[Rajouani, N., Ait Itto, My. Y., Benharref, A., Auhmani, A. & Daran, J.-C. (2008). Acta Cryst. E64, o762.]).

[Scheme 1]

Experimental

Crystal data
  • C13H18O3

  • Mr = 222.27

  • Monoclinic, P 21 /c

  • a = 10.829 (2) Å

  • b = 9.600 (2) Å

  • c = 12.530 (3) Å

  • [beta] = 100.34 (2)°

  • V = 1281.4 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 300 K

  • 0.3 × 0.15 × 0.1 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.521, Tmax = 0.992

  • 3366 measured reflections

  • 2780 independent reflections

  • 1594 reflections with I > 2[sigma](I)

  • Rint = 0.018

  • 2 standard reflections every 60 min intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.132

  • S = 1.02

  • 2780 reflections

  • 151 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H1...O2i 0.93 2.60 3.523 (3) 171
Symmetry code: (i) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 EXPRESS. Enraf-Nonius, Deft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990[Fair, C. K. (1990). MolEN. Enraf-Nonius, Delft, The Netherlands.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5314 ).


References

Enraf-Nonius (1989). CAD-4 EXPRESS. Enraf-Nonius, Deft, The Netherlands.
Fair, C. K. (1990). MolEN. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Osorio, E., Arango, G., Robledo, S., Muñoz, D., Jaramillo, L. & Vélez, I. (2006). Acta Farm. Bonaer. 25, 405-413.  [ChemPort]
Rajouani, N., Ait Itto, My. Y., Benharref, A., Auhmani, A. & Daran, J.-C. (2008). Acta Cryst. E64, o762.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Ündeger, Ü., Basaran, A., Degen, G. H. & Basaran, N. (2009). Food Chem. Toxicol. 47, 2037-2043.  [Web of Science] [PubMed]
Yuan-Lang, C. & Erdtman, H. (1962). Acta Chem. Scand. 16, 1291-1295.


Acta Cryst (2013). E69, o1715  [ doi:10.1107/S160053681302922X ]

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