3,4,5-Trimeth­oxy­phenol

Jia, X.-C.; Li, J.; Yu, Z.-R.; Zhang, H.; Zhou, L.

doi:10.1107/S1600536812042997

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 (C-C) = 0.002 Å
R = 0.051
wR = 0.123
Data-to-parameter ratio = 13.4
Details

3,4,5-Trimethoxyphenol

Xiao-Chuan Jia,^a ^* Jing Li,^a Zhi-Rui Yu,^a Hui Zhang ^a and Lei Zhou ^a

^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-HO hydrogen bonds link the molecules, generating supramolecular chains along the b axis.The three-dimensional crystal structure is stabilized by C-HO 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); Gong et al. (2009).

Experimental

Crystal data

C₉H₁₂O₄
M_r = 184.19
Monoclinic, P 2₁ /c
a = 15.355 (3) Å
b = 11.139 (2) Å
c = 11.546 (2) Å
= 111.38 (3)°
V = 1839.0 (6) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.981, T_max = 0.990
16747 measured reflections
3257 independent reflections
2957 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.123
S = 1.05
3257 reflections
243 parameters
H-atom parameters constrained
_max = 0.12 e Å^-3
_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-HA	D-H	HA	DA	D-HA
O5-H5O7ⁱ	0.82	1.93	2.7484 (18)	179
O1-H1O3ⁱⁱ	0.82	1.90	2.7204 (17)	175
C6-H6AO1ⁱⁱⁱ	0.96	2.57	3.256 (3)	129
C15-H15AO5^iv	0.96	2.59	3.270 (3)	128
C4-H4BCg1^v	0.96	2.86	3.777 (2)	160
C17-H17BCg2^vi	0.96	2.85	3.736 (2)	154
C13-H13BO1^vii	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Matos, M. A. R., Miranda, M. S. & Morais, V. M. F. (2008). J. Chem. Thermodyn. 40, 625-631.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds