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Volume 70 
Part 1 
Page o75  
January 2014  

Received 11 December 2013
Accepted 13 December 2013
Online 21 December 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.119
Data-to-parameter ratio = 18.4
Details
Open access

(1S*,2S*,4R*,5R*)-Cyclo­hexane-1,2,4,5-tetra­carb­oxy­lic acid

aDepartment of Biomolecular Science, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan,bDepartment of Chemistry, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan, and cDepartment of Research and Development, Gas Chemical Division, Iwatani Industrial Gases Corporation Ltd., 10 Otakasu-cho, Amagasaki, Hyogo 660-0842, Japan
Correspondence e-mail: auchida@biomol.sci.toho-u.ac.jp

The title compound, C10H12O8, a prospective raw material for colourless polyimides which are applied to electronic and microelectronic devices, lies about an inversion centre and the cyclo­hexane ring adopts a chair conformation. Two crystallographycally independent carb­oxy­lic acid groups on adjacent C atoms are in equatorial positions, resulting in a mutually trans conformation. In the crystal, O-H...O hydrogen bonds around an inversion centre and a threefold rotoinversion axis, respectively, form an inversion dimer with an R22(8) motif and a trimer with an R33(12) motif.

Related literature

For background to polyimides, see: Ando et al. (2010[Ando, S., Ueda, M., Kakimoto, M., Kochi, M., Takeichi, T., Hasegawa, M. & Yokota, R. (2010). In The Latest Polyimides: Fundamentals and Applications, 2nd ed. Tokyo: NTS.]); Hasegawa et al. (2007[Hasegawa, M., Horiuchi, M. & Wada, Y. (2007). High Perform. Polym. 19, 175-193.], 2013[Hasegawa, M., Hirano, D., Fujii, M., Haga, M., Takezawa, E., Yamaguchi, S., Ishikawa, A. & Kagayama, T. (2013). J. Polym. Sci. Part A, 51, 575-592.]); Hasegawa & Horie (2001[Hasegawa, M. & Horie, K. (2001). Prog. Polym. Sci. 26, 259-335.]). For related structures, see: Uchida et al. (2003[Uchida, A., Hasegawa, M. & Manami, H. (2003). Acta Cryst. C59, o435-o438.], 2012[Uchida, A., Hasegawa, M., Takezawa, E., Yamaguchi, S., Ishikawa, A. & Kagayama, T. (2012). Acta Cryst. E68, o579.]).

[Scheme 1]

Experimental

Crystal data
  • C10H12O8

  • Mr = 260.20

  • Trigonal, [R \overline 3]

  • a = 17.6970 (6) Å

  • c = 9.5455 (6) Å

  • V = 2589.0 (2) Å3

  • Z = 9

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 298 K

  • 0.33 × 0.26 × 0.26 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.891, Tmax = 0.966

  • 6439 measured reflections

  • 1653 independent reflections

  • 1388 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.119

  • S = 1.06

  • 1653 reflections

  • 90 parameters

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

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H4...O1i 0.81 (3) 1.93 (3) 2.705 (2) 160 (3)
O4-H5...O3ii 0.94 (3) 1.70 (3) 2.632 (1) 176 (3)
Symmetry codes: (i) -x+y+1, -x+1, z; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2007[Bruker (2007). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2013.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5327 ).


References

Ando, S., Ueda, M., Kakimoto, M., Kochi, M., Takeichi, T., Hasegawa, M. & Yokota, R. (2010). In The Latest Polyimides: Fundamentals and Applications, 2nd ed. Tokyo: NTS.
Bruker (2007). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Hasegawa, M., Hirano, D., Fujii, M., Haga, M., Takezawa, E., Yamaguchi, S., Ishikawa, A. & Kagayama, T. (2013). J. Polym. Sci. Part A, 51, 575-592.  [CrossRef] [ChemPort]
Hasegawa, M. & Horie, K. (2001). Prog. Polym. Sci. 26, 259-335.  [CrossRef] [ChemPort]
Hasegawa, M., Horiuchi, M. & Wada, Y. (2007). High Perform. Polym. 19, 175-193.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Uchida, A., Hasegawa, M. & Manami, H. (2003). Acta Cryst. C59, o435-o438.  [CSD] [CrossRef] [IUCr Journals]
Uchida, A., Hasegawa, M., Takezawa, E., Yamaguchi, S., Ishikawa, A. & Kagayama, T. (2012). Acta Cryst. E68, o579.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2014). E70, o75  [ doi:10.1107/S1600536813033795 ]

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