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Volume 68 
Part 11 
Page o3160  
November 2012  

Received 12 October 2012
Accepted 15 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.123
Data-to-parameter ratio = 13.4
Details
Open access

3,4,5-Trimethoxyphenol

aTianjin Entry-Exit Inspection and Quarantine Bureau, Tianjin 300201, People's Republic of China
Correspondence e-mail: xiaochuanjia2012@163.com

The asymmetric unit of the title compound, C9H12O4, consists of two crystallographically independent molecules with similar conformations: essentially planar [r.m.s deviations for C6O4 = 0.0057 and 0.0137 Å] except for the central methoxy-methyl group [C-C-O-C torsion angles = 83.3 (2) and 83.9 (2)°]. In the crystal, O-H...O hydrogen bonds link the molecules, generating supramolecular chains along the b axis.The three-dimensional crystal structure is stabilized by C-H...O and C-H...[pi] interactions.

Related literature

For background information on the energetics and anti-oxidant potential of phenolic compounds, see: Matos et al. (2008[Matos, M. A. R., Miranda, M. S. & Morais, V. M. F. (2008). J. Chem. Thermodyn. 40, 625-631.]); Gong et al. (2009[Gong, J. X., Huang, K. X., Wang, F., Yang, L. X., Feng, Y. B., Li, H. B., Li, X. K., Zeng, S., Wu, X. M., Stöckigt, J., Zhao, Y. & Qu, J. (2009). Bioorg. Med. Chem. 17, 3414-3425.]).

[Scheme 1]

Experimental

Crystal data
  • C9H12O4

  • Mr = 184.19

  • Monoclinic, P 21 /c

  • a = 15.355 (3) Å

  • b = 11.139 (2) Å

  • c = 11.546 (2) Å

  • [beta] = 111.38 (3)°

  • V = 1839.0 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.20 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.990

  • 16747 measured reflections

  • 3257 independent reflections

  • 2957 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.123

  • S = 1.05

  • 3257 reflections

  • 243 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C3,C5,C7,C9 and C10-C12,C14,C16,C18 benzene rings, respectively.

D-H...A D-H H...A D...A D-H...A
O5-H5...O7i 0.82 1.93 2.7484 (18) 179
O1-H1...O3ii 0.82 1.90 2.7204 (17) 175
C6-H6A...O1iii 0.96 2.57 3.256 (3) 129
C15-H15A...O5iv 0.96 2.59 3.270 (3) 128
C4-H4B...Cg1v 0.96 2.86 3.777 (2) 160
C17-H17B...Cg2vi 0.96 2.85 3.736 (2) 154
C13-H13B...O1vii 0.96 2.49 3.303 (3) 142
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+2, -z; (v) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (vi) [x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]; (vii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5160 ).


Acknowledgements

We thank the Tianjin Entry-Exit Inspection and Quarantine Bureau for financial support.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gong, J. X., Huang, K. X., Wang, F., Yang, L. X., Feng, Y. B., Li, H. B., Li, X. K., Zeng, S., Wu, X. M., Stöckigt, J., Zhao, Y. & Qu, J. (2009). Bioorg. Med. Chem. 17, 3414-3425.  [CrossRef] [PubMed] [ChemPort]
Matos, M. A. R., Miranda, M. S. & Morais, V. M. F. (2008). J. Chem. Thermodyn. 40, 625-631.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3160  [ doi:10.1107/S1600536812042997 ]

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