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Volume 67 
Part 2 
Pages o316-o317  
February 2011  

Received 3 December 2010
Accepted 4 January 2011
Online 12 January 2011

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Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.001 Å
R = 0.034
wR = 0.103
Data-to-parameter ratio = 21.9
Details
Open access

Gallic acid

Jianping Zhao,a Ikhlas A. Khana,b and Frank R. Fronczekc*

aNational Center for Natural Products Research, RIPS, School of Pharmacy, University of Mississippi, University, MS 38677, USA,bDepartment of Pharmacognosy, RIPS, School of Pharmacy, University of Mississippi, University, MS 38677, USA, and cDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
Correspondence e-mail: ffroncz@lsu.edu

Anhydrous 3,4,5-trihydroxybenzoic acid, C7H6O5, is essentially planar, with its non-H atoms exhibiting mean and maximum deviations from coplanarity of 0.014 and 0.0377 (5) Å, respectively. The C-C-C-OH torsion angle about the bond linking the carboxyl group to the benzene ring is -0.33 (10)°. In the crystal, the -COOH groups form centrosymmetric hydrogen-bonded cyclic dimers [graph set R22(8)] and the phenolic -OH groups participate in both intra- and intermolecular hydrogen bonds, forming a three-dimensional network structure.

Related literature

For distribution of gallic acid in plants and for biological studies, see: Fiuza et al. (2004[Fiuza, S. M., Gomes, C., Teixeira, L. J., Girão da Cruz, M. T., Cordeiro, M. N. D. S., Milhazes, N., Borges, F. & Marques, M. P. M. (2004). Bioorg. Med. Chem. 12, 3581-3589.]); Ow & Stupans (2003[Ow, Y. Y. & Stupans, I. (2003). Curr. Drug Metab. 4, 241-248.]); Hemingway et al. (1999[Hemingway, R. W., Gross, G. G. & Yoshida, T. (1999). Plant Polyphenols: Chemistry and Biology, pp. 495-505. New York: Plenum Press.]). For NMR data, see: Lu et al. (2007[Lu, J. J., Wei, Y. & Yuan, Q. P. (2007). Sep. Purif. Technol. 55, 40-43.]). For graph sets, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]); Zaheer et al. (2010[Zaheer, S., Lenin, R., Thangavel, S., Ashok, V., Viswanathan, M. & Muthuswamy, B. (2010). Phytother. Res. Suppl. 1, S83-S94.]). For related structures, see: Jiang et al. (2000[Jiang, R.-W., Ming, D.-S., But, P. P. H. & Mak, T. C. W. (2000). Acta Cryst. C56, 594-595.]); Okabe et al. (2001[Okabe, N., Kyoyama, H. & Suzuki, M. (2001). Acta Cryst. E57, o764-o766.]); Billes et al. (2007[Billes, F., Mohammed-Ziegler, I. & Bombicz, P. (2007). Vibr. Spectrosc. 43, 193-202.]); Qadeer et al. (2007[Qadeer, G., Rama, N. H., Tas, M., Yesilel, O. Z. & Wong, W.-Y. (2007). Acta Cryst. E63, o3456.]).

[Scheme 1]

Experimental

Crystal data

  • C7H6O5

  • Mr = 170.12

  • Monoclinic, C 2/c

  • a = 25.690 (4) Å

  • b = 4.8946 (5) Å

  • c = 11.097 (2) Å

  • [beta] = 105.746 (6)°

  • V = 1343.0 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 90 K

  • 0.25 × 0.23 × 0.15 mm
Data collection

  • Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler

  • 17352 measured reflections

  • 2674 independent reflections

  • 2391 reflections with I > 2[sigma](I)

  • Rint = 0.016
Refinement

  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.103

  • S = 1.06

  • 2674 reflections

  • 122 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.62 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H20...O1i 0.910 (15) 1.730 (15) 2.6384 (8) 175.6 (13)
O3-H30...O3ii 0.881 (14) 1.964 (14) 2.7943 (5) 156.6 (12)
O3-H30...O4 0.881 (14) 2.345 (13) 2.7579 (9) 108.8 (10)
O4-H40...O5 0.838 (14) 2.191 (13) 2.6688 (8) 116.1 (11)
O5-H50...O1iii 0.893 (14) 1.828 (14) 2.7200 (8) 178.6 (14)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+1, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2084 ).

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF(1999-2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Billes, F., Mohammed-Ziegler, I. & Bombicz, P. (2007). Vibr. Spectrosc. 43, 193-202.  [CrossRef] [ChemPort]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Fiuza, S. M., Gomes, C., Teixeira, L. J., Girão da Cruz, M. T., Cordeiro, M. N. D. S., Milhazes, N., Borges, F. & Marques, M. P. M. (2004). Bioorg. Med. Chem. 12, 3581-3589.  [CrossRef] [PubMed] [ChemPort]
Hemingway, R. W., Gross, G. G. & Yoshida, T. (1999). Plant Polyphenols: Chemistry and Biology, pp. 495-505. New York: Plenum Press.
Jiang, R.-W., Ming, D.-S., But, P. P. H. & Mak, T. C. W. (2000). Acta Cryst. C56, 594-595.  [CSD] [CrossRef] [details]
Lu, J. J., Wei, Y. & Yuan, Q. P. (2007). Sep. Purif. Technol. 55, 40-43.  [ChemPort]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Okabe, N., Kyoyama, H. & Suzuki, M. (2001). Acta Cryst. E57, o764-o766.  [CSD] [CrossRef] [details]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Ow, Y. Y. & Stupans, I. (2003). Curr. Drug Metab. 4, 241-248.  [ISI] [CrossRef] [PubMed] [ChemPort]
Qadeer, G., Rama, N. H., Tas, M., Yesilel, O. Z. & Wong, W.-Y. (2007). Acta Cryst. E63, o3456.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zaheer, S., Lenin, R., Thangavel, S., Ashok, V., Viswanathan, M. & Muthuswamy, B. (2010). Phytother. Res. Suppl. 1, S83-S94.

Acta Cryst (2011). E67, o316-o317   [ doi:10.1107/S1600536811000262 ]

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