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Volume 64 
Part 7 
Page o1366  
July 2008  

Received 14 May 2008
Accepted 20 June 2008
Online 28 June 2008

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.113
Data-to-parameter ratio = 16.3
Details
Open access

Trimesic acid dimethyl sulfoxide solvate: space group revision

Sylvain Bernès,a* Guadalupe Hernández,b Roberto Portillob and René Gutiérrezb

aDEP Facultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, NL, Mexico, and bLaboratorio de Síntesis de Complejos, Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, AP 1067, 72001 Puebla, Pue., Mexico
Correspondence e-mail: sylvain_bernes@Hotmail.com

The structure of the title solvate, C9H6O6·C2H6OS, was determined 30 years ago [Herbstein, Kapon & Wasserman (1978[Herbstein, F. H., Kapon, M. & Wasserman, S. (1978). Acta Cryst. B34, 1613-1617.]). Acta Cryst. B34, 1613-1617], with data collected at room temperature, and refined in the space group P21. The present redetermination, based on high-resolution diffraction data, shows that the actual space group is more likely to be P21/m. The crystal structure contains layers of trimesic acid molecules lying on mirror planes. A mirror plane also passes through the S and O atoms of the solvent molecule. The molecules in each layer are interconnected through strong O-H...O hydrogen bonds, forming a two-dimensional supramolecular network within each layer. The donor groups are the hydroxyls of the trimesic acid molecules, while the acceptors are the carbonyl or the sulfoxide O atoms.

Related literature

For the first report on the title solvate structure, see: Herbstein et al. (1978[Herbstein, F. H., Kapon, M. & Wasserman, S. (1978). Acta Cryst. B34, 1613-1617.]). For the use of trimesic acid as a building block for supramolecular networks, see: Almeida Paz & Klinowski (2004[Almeida Paz, F. A. & Klinowski, J. (2004). Inorg. Chem. 43, 3882-3893.]). For a description of hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond In Structural Chemistry and Biology, p. 13. International Union of Crystallography Monographs on Crystallography. Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data

  • C9H6O6·C2H6OS

  • Mr = 288.27

  • Monoclinic, P 21 /m

  • a = 8.7444 (7) Å

  • b = 6.8365 (7) Å

  • c = 10.7113 (8) Å

  • [beta] = 96.195 (5)°

  • V = 636.59 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 298 (1) K

  • 0.60 × 0.48 × 0.36 mm
Data collection

  • Siemens P4 diffractometer

  • Absorption correction: [psi] scan (XSCANS; Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.851, Tmax = 0.904

  • 4582 measured reflections

  • 2007 independent reflections

  • 1772 reflections with I > 2[sigma](I)

  • Rint = 0.015

  • 3 standard reflections every 97 reflections intensity decay: <1%
Refinement

  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.112

  • S = 1.07

  • 2007 reflections

  • 123 parameters

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

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O6i 0.84 (3) 1.82 (3) 2.6435 (16) 165 (3)
O3-H3...O7ii 0.85 (4) 1.83 (4) 2.6593 (17) 164 (4)
O5-H5...O7iii 0.86 (3) 1.73 (3) 2.5723 (16) 169 (3)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) x+1, y, z+1.

Data collection: XSCANS (Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2098 ).

Acknowledgements

Partial support from VIEP-BUAP (14/G/NAT/05) is acknowledged. SB thanks BUAP for diffractometer time.

References

Almeida Paz, F. A. & Klinowski, J. (2004). Inorg. Chem. 43, 3882-3893.  [CrossRef] [PubMed]
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond In Structural Chemistry and Biology, p. 13. International Union of Crystallography Monographs on Crystallography. Oxford University Press.
Herbstein, F. H., Kapon, M. & Wasserman, S. (1978). Acta Cryst. B34, 1613-1617.  [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Acta Cryst (2008). E64, o1366  [ doi:10.1107/S1600536808018655 ]

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