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Volume 69 
Part 6 
Pages o908-o909  
June 2013  

Received 18 April 2013
Accepted 13 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.024
wR = 0.059
Data-to-parameter ratio = 13.5
Details
Open access

5,5'-(Ethyne-1,2-diyl)diisophthalic acid dimethyl sulfoxide tetrasolvate

aInstitute of Physical Chemistry, Technical University Bergakademie Freiberg, Leipziger Strasse 29, 09596 Freiberg/Sachsen, Germany, and bInstitute of Organic Chemistry, Technical University Bergakademie Freiberg, Leipziger Strasse 29, 09596 Freiberg/Sachsen, Germany
Correspondence e-mail: florian.mertens@chemie.tu-freiberg.de

In the title compound, C18H10O8·4C2H6OS, the mid-point of the triple bond of the main molecule is located on a special position, i.e. about an inversion center. The carboxyl groups are twisted slightly out of the planes of the aromatic rings to which they are attached, making dihedral angles of 24.89 (1) and 7.40 (2)°. The cystal packing features strong O-H...O hydrogen bonds, weaker C-H...O interactions and O...S contacts [3.0981 (11) Å] and displays channel-like voids extending along the a-axis direction which contain the dimethyl sulfoxide solvent molecules.

Related literature

For the synthesis of the principal compound, see: Hausdorf et al. (2009[Hausdorf, S., Seichter, W., Weber, E. & Mertens, F. O. R. L. (2009). Dalton Trans. pp. 1107-1113.]); Zhou et al. (2007[Zhou, H., Dang, H., Yi, J.-H., Nanci, A., Rochefort, A. & Wuest, J.-D. (2007). J. Am. Chem. Soc. 129, 13774-13775.]). For its use as linker molecule in the formation of porous metal-organic framework structures, see: Hausdorf et al. (2009[Hausdorf, S., Seichter, W., Weber, E. & Mertens, F. O. R. L. (2009). Dalton Trans. pp. 1107-1113.]); Hu et al. (2009[Hu, Y., Xiang, X., Zhang, W., Wang, L., Bai, J. & Chen, B. (2009). Chem. Commun. 48, 7551-7553.]); Zheng et al. (2013[Zheng, B., Luo, J., Wang, F., Peng, Y., Li, G., Huo, Q. & Liu, Y. (2013). Cryst. Growth Des. 13, 1033-1044.]). For metal-organic frameworks, see: Münch et al. (2011[Münch, A. S., Seidel, J., Obst, A., Weber, E. & Mertens, F. O. R. L. (2011). Chem. Eur. J. 17, 10958-10964.]); Chen et al. (2005[Chen, B., Ockwig, N. W., Millward, A. R., Contreras, D. S. & Yaghi, O. M. (2005). Angew. Chem. Int. Ed. 44, 4745-4749.]); Coles et al. (2002[Coles, S. J., Holmes, R., Hursthouse, M. B. & Price, D. J. (2002). Acta Cryst. E58, o626-o628.]). For a similar hydrogen-bonded aggregate, see: Hauptvogel et al. (2011[Hauptvogel, I., Seichter, W. & Weber, E. (2011). Supramol. Chem. 23, 398-406.]). For O-H...O hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1563.]); Katzsch et al. (2011[Katzsch, F., Eissmann, D. & Weber, E. (2011). Struct. Chem. 23, 245-255.]). For C-H...O contacts, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.]); Katzsch & Weber (2012[Katzsch, F. & Weber, E. (2012). Acta Cryst. E68, o2354-o2355.]); Fischer et al. (2011[Fischer, C., Gruber, T., Seichter, W. & Weber, E. (2011). Org. Biomol. Chem. 9, 4347-4352.]). For O...S contacts, see: Lu et al. (2011[Lu, J., Lu, Y., Yang, S. & Zhu, W. (2011). Struct. Chem. 22, 757-763.]). For [pi]-[pi] interactions, see: Hunter & Sanders (1990[Hunter, C. A. & Sanders, J. K. M. (1990). J. Am. Chem. Soc. 112, 5525-5534.]).

[Scheme 1]

Experimental

Crystal data
  • C18H10O8·4C2H6OS

  • Mr = 666.81

  • Monoclinic, P 21 /n

  • a = 8.1406 (2) Å

  • b = 8.7328 (2) Å

  • c = 21.4351 (5) Å

  • [beta] = 95.970 (1)°

  • V = 1515.56 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 100 K

  • 0.60 × 0.42 × 0.36 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.807, Tmax = 0.877

  • 20635 measured reflections

  • 2666 independent reflections

  • 2567 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.059

  • S = 1.04

  • 2666 reflections

  • 197 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O1Gi 0.84 1.71 2.5451 (13) 171
O3-H3...O1Hii 0.84 1.76 2.5732 (13) 161
C1G-H1G2...O2iii 0.98 2.56 3.3138 (17) 134
C1G-H1G3...O4iv 0.98 2.71 3.5351 (17) 143
C2G-H2G1...O1Hv 0.98 2.57 3.5093 (18) 160
C2G-H2G2...O2iii 0.98 2.52 3.2783 (17) 135
C1H-H1H1...O4vi 0.98 2.57 3.5006 (18) 159
C1H-H1H2...O4vii 0.98 2.69 3.4427 (18) 134
C2H-H2H1...O1Hv 0.98 2.52 3.3409 (17) 141
C2H-H2H2...O1viii 0.98 2.67 3.4738 (17) 139
C2H-H2H2...O1Gix 0.98 2.54 3.1574 (17) 121
C2H-H2H2...O4vii 0.98 2.70 3.4604 (18) 135
Symmetry codes: (i) x-1, y, z+1; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) -x, -y+1, -z+1; (iv) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (v) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (vii) -x, -y+2, -z+1; (viii) x, y, z-1; (ix) x-1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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: RK2402 ).


Acknowledgements

Financial support by the Deutsche Forschungsgemeinschaft (Priority Program 1362 "Porous Metal-Organic Frameworks") is gratefully acknowledged by A·M. F·K. thanks the European Union (European regional development fund) and the Ministry of Science and Art of Saxony (Cluster of Excellence "Structure Design of Novel High-Performance Materials via Atomic Design and Defect Engineering [ADDE]").

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1563.  [ChemPort]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, B., Ockwig, N. W., Millward, A. R., Contreras, D. S. & Yaghi, O. M. (2005). Angew. Chem. Int. Ed. 44, 4745-4749.  [ISI] [CSD] [CrossRef] [ChemPort]
Coles, S. J., Holmes, R., Hursthouse, M. B. & Price, D. J. (2002). Acta Cryst. E58, o626-o628.  [CSD] [CrossRef] [ChemPort] [details]
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.
Fischer, C., Gruber, T., Seichter, W. & Weber, E. (2011). Org. Biomol. Chem. 9, 4347-4352.  [CSD] [CrossRef] [ChemPort] [PubMed]
Hauptvogel, I., Seichter, W. & Weber, E. (2011). Supramol. Chem. 23, 398-406.  [ISI] [CSD] [CrossRef] [ChemPort]
Hausdorf, S., Seichter, W., Weber, E. & Mertens, F. O. R. L. (2009). Dalton Trans. pp. 1107-1113.  [CSD] [CrossRef]
Hu, Y., Xiang, X., Zhang, W., Wang, L., Bai, J. & Chen, B. (2009). Chem. Commun. 48, 7551-7553.  [CSD] [CrossRef]
Hunter, C. A. & Sanders, J. K. M. (1990). J. Am. Chem. Soc. 112, 5525-5534.  [CrossRef] [ChemPort] [ISI]
Katzsch, F., Eissmann, D. & Weber, E. (2011). Struct. Chem. 23, 245-255.  [ISI] [CSD] [CrossRef]
Katzsch, F. & Weber, E. (2012). Acta Cryst. E68, o2354-o2355.  [CSD] [CrossRef] [ChemPort] [details]
Lu, J., Lu, Y., Yang, S. & Zhu, W. (2011). Struct. Chem. 22, 757-763.  [ISI] [CrossRef] [ChemPort]
Münch, A. S., Seidel, J., Obst, A., Weber, E. & Mertens, F. O. R. L. (2011). Chem. Eur. J. 17, 10958-10964.  [PubMed]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Zheng, B., Luo, J., Wang, F., Peng, Y., Li, G., Huo, Q. & Liu, Y. (2013). Cryst. Growth Des. 13, 1033-1044.  [CrossRef] [ChemPort]
Zhou, H., Dang, H., Yi, J.-H., Nanci, A., Rochefort, A. & Wuest, J.-D. (2007). J. Am. Chem. Soc. 129, 13774-13775.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o908-o909   [ doi:10.1107/S1600536813013068 ]

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