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Volume 70 
Part 5 
Page o615  
May 2014  

Received 5 March 2014
Accepted 15 April 2014
Online 30 April 2014

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.136
Data-to-parameter ratio = 11.6
Details
Open access

4,4'-Dimeth­oxybi­phenyl-3,3'-di­car­box­ylic acid

aCentre for Materials Science and Nanotechnology, Department of Chemistry, University of Oslo, PO Box 1126, 0315 Oslo, Norway,binGAP National Centre of Research-based Innovation, Department of Chemistry, University of Oslo, PO Box 1126, 0315 Oslo, Norway, and cDepartment of Chemistry, University of Bergen, PO Box 7803, 5020 Bergen, Norway
Correspondence e-mail: fredrik.lundvall@smn.uio.no

The title compound, C16H14O6, was recrystallized under solvothermal conditions. The mol­ecules are located on inversion centres, with one complete mol­ecule generated from the asymmetric unit by inversion. There are intra­molecular O-H...O hydrogen bonds involving the carb­oxy­lic acid group and the O atom of the adjacent meth­oxy group. In the crystal, mol­ecules are linked via O-H...O hydrogen bonds, forming chains propagating along [100]. The chains are linked via C-H...O hydrogen bonds, forming sheets parallel to (001).

Related literature

For the synthesis, see Wang et al. (2009[Wang, L., Xiao, Z.-Y., Hou, J.-L., Wang, G.-T., Jiang, X.-K. & Li, Z.-T. (2009). Tetrahedron, 65, 10544-10551.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14O6

  • Mr = 302.27

  • Orthorhombic, I b a m

  • a = 13.138 (2) Å

  • b = 15.615 (3) Å

  • c = 6.7726 (11) Å

  • V = 1389.4 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.65 × 0.10 × 0.09 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.931, Tmax = 0.990

  • 5188 measured reflections

  • 779 independent reflections

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

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.136

  • S = 1.12

  • 779 reflections

  • 67 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3 0.82 1.85 2.545 (2) 141
O1-H1...O1i 0.82 2.42 2.816 (3) 111
C5-H5...O2ii 0.93 2.41 3.341 (2) 175
Symmetry codes: (i) -x, -y+1, z; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -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: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2004[Brandenburg, K. (2004). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and ChemBioDraw Ultra (CambridgeSoft, 2009[CambridgeSoft (2009). ChemBioDraw Ultra. CambridgeSoft Corporation, Cambridge, Massachusetts, USA.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: QM2105 ).


Acknowledgements

We acknowledge the support from the Norwegian Research Council (project 190980), inGAP and the Department of Chemistry, UiO.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [IUCr Journals]
Brandenburg, K. (2004). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
CambridgeSoft (2009). ChemBioDraw Ultra. CambridgeSoft Corporation, Cambridge, Massachusetts, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wang, L., Xiao, Z.-Y., Hou, J.-L., Wang, G.-T., Jiang, X.-K. & Li, Z.-T. (2009). Tetrahedron, 65, 10544-10551.  [Web of Science] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o615  [ doi:10.1107/S1600536814008599 ]

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