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Volume 69 
Part 6 
Pages o912-o913  
June 2013  

Received 17 April 2013
Accepted 6 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.004 Å
R = 0.045
wR = 0.100
Data-to-parameter ratio = 16.2
Details
Open access

5-(Naphthalen-1-yl)isophthalic acid-dimethyl sulfoxide-water (2/1/2)

aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
Correspondence e-mail: Edwin.Weber@chemie.tu-freiberg.de

The asymmetric unit of the title compound, 2C18H12O4·C2H6OS·2H2O, consists of four crystallographically independent molecules of 5-(naphthalen-1-yl)isophthalic acid, two dimethyl sulfoxide and four water molecules. The dihedral angles formed by the the planes of the aromatic fragments of the organic molecules range from 57.4 (1) to 59.1 (1)°. In the crystal, multiple O-H...O hydrogen bonds link the water molecules with the carbonyl and sulfoxide groups, giving rise to double ribbons along the b-axis direction.

Related literature

For preparative methods used for the synthesis of the title compound, see: Broutin & Colobert (2005[Broutin, P.-E. & Colobert, F. (2005). Eur. J. Org. Chem. pp. 1113-1128.]); Mazik & König (2006[Mazik, M. & König, A. (2006). J. Org. Chem. 71, 7854-7857.]); Miyaura et al. (1981[Miyaura, N., Yanagi, T. & Suzuki, A. (1981). Synth. Commun. 11, 513-519.]). For the structure of isophthalic acid, see: Derissen (1974[Derissen, J. L. (1974). Acta Cryst. B30, 2764-2765.]). For hydrogen-bonding patterns, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.]); Burrows (2004[Burrows, A. D. (2004). Struct. Bond. 108, 55-96.]). For [pi]-[pi] stacking interactions, see: James (2004[James, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093-1099. Boca Raton: CRC Press.]). For C-H...O interactions, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. New York: Oxford University Press Inc.]). For organic crystal engineering aspects, see: Tiekink et al. (2010[Tiekink, E. R. T., Vittal, J. J. & Zaworotko, M. J. (2010). Editors. Organic Crystal Engineering. Chichester: Wiley.]).

[Scheme 1]

Experimental

Crystal data
  • 2C18H12O4·C2H6OS·2H2O

  • Mr = 698.72

  • Triclinic, P 1

  • a = 6.6842 (4) Å

  • b = 9.6173 (6) Å

  • c = 25.4682 (15) Å

  • [alpha] = 95.780 (3)°

  • [beta] = 95.669 (3)°

  • [gamma] = 90.028 (3)°

  • V = 1620.82 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 93 K

  • 0.18 × 0.17 × 0.09 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • 39842 measured reflections

  • 15284 independent reflections

  • 12600 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.100

  • S = 1.04

  • 15284 reflections

  • 945 parameters

  • 8 restraints

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 7387 Friedel pairs

  • Flack parameter: -0.03 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O1Wi 0.84 1.72 2.559 (2) 175
O1B-H1B...O3W 0.84 1.74 2.573 (2) 168
O2A-H2A...O4Aii 0.84 1.82 2.583 (2) 151
O2C-H2C...O4Cii 0.84 1.81 2.584 (2) 152
O3A-H3A...O2Wiii 0.84 1.73 2.565 (3) 174
O3C-H3C...O4W 0.84 1.72 2.561 (2) 176
O4-H4...O2iii 0.84 1.81 2.591 (2) 154
O4B-H4B...O2Biii 0.84 1.81 2.578 (2) 150
O1W-H1W1...O1Hiv 0.85 (3) 1.92 (3) 2.716 (3) 155 (3)
O1W-H2W1...O3v 0.85 (3) 2.04 (3) 2.858 (2) 162 (3)
O2W-H1W2...O1Gvi 0.85 (3) 1.91 (3) 2.742 (3) 168 (3)
O2W-H2W2...O1A 0.85 (2) 2.03 (2) 2.879 (2) 174 (3)
O3W-H1W3...O1Gvii 0.85 (2) 1.85 (2) 2.680 (3) 165 (3)
O3W-H2W3...O3Bii 0.85 (2) 1.98 (2) 2.824 (2) 170 (3)
O4W-H1W4...O1Hvii 0.85 (2) 1.84 (2) 2.656 (3) 162 (3)
O4W-H2W4...O1Ciii 0.86 (3) 1.96 (3) 2.808 (2) 172 (3)
Symmetry codes: (i) x-1, y+1, z; (ii) x, y+1, z; (iii) x, y-1, z; (iv) x, y, z+1; (v) x+1, y, z; (vi) x-1, y, z+1; (vii) x-1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2092 ).


Acknowledgements

The authors thank the Deutsche Forschungsgemeinschaft (DFG) for financial support (SPP 1362/1).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Broutin, P.-E. & Colobert, F. (2005). Eur. J. Org. Chem. pp. 1113-1128.  [CSD] [CrossRef]
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burrows, A. D. (2004). Struct. Bond. 108, 55-96.  [CrossRef] [ChemPort]
Derissen, J. L. (1974). Acta Cryst. B30, 2764-2765.  [CrossRef] [details]
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. New York: Oxford University Press Inc.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
James, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093-1099. Boca Raton: CRC Press.
Mazik, M. & König, A. (2006). J. Org. Chem. 71, 7854-7857.  [CrossRef] [PubMed] [ChemPort]
Miyaura, N., Yanagi, T. & Suzuki, A. (1981). Synth. Commun. 11, 513-519.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Tiekink, E. R. T., Vittal, J. J. & Zaworotko, M. J. (2010). Editors. Organic Crystal Engineering. Chichester: Wiley.


Acta Cryst (2013). E69, o912-o913   [ doi:10.1107/S1600536813012361 ]

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