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Volume 67 
Part 4 
Page o968  
April 2011  

Received 19 March 2011
Accepted 19 March 2011
Online 26 March 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.091
Data-to-parameter ratio = 9.3
Details
Open access

2-[(1R*,4R*)-1,4-Dihydroxycyclohexyl]acetic acid

aInstitute of Chemical Sciences, University of Peshawar, Peshawar, Pakistan,bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and cInternational Centre for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

The title compound, C8H14O4, is an isolation product of the aerial parts of Senecio desfontanei. The acetic acid group is oriented at a dihedral angle of 48.03 (9)° with respect to the basal plane of the cyclohexane-1,4-diol chair. An intramolecular O-H...O hydrogen bond generates an S(6) ring with an envelope conformation. In the crystal, molecules are linked by O-H...O hydrogen bonds, resulting in R33(20) ring motifs and C(2) O-H...O-H...O-H... chains. Overall, a three-dimensional polymeric network arises. A C-H...O contact is also present.

Related literature

For related structures, see: Jasinski et al. (2009[Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Mallesha, L., Mohana, K. N. & Narayana, B. (2009). J. Chem. Crystallogr. 39, 777-780.]); Vasudev et al. (2008[Vasudev, P. G., Rai, R., Shamala, N. & Balaram, P. (2008). Biopolymers, 90, 138-150.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C8H14O4

  • Mr = 174.19

  • Triclinic, P 1

  • a = 5.7301 (4) Å

  • b = 6.3493 (3) Å

  • c = 6.4964 (4) Å

  • [alpha] = 92.863 (2)°

  • [beta] = 97.223 (1)°

  • [gamma] = 108.258 (2)°

  • V = 221.67 (2) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.28 × 0.12 × 0.10 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.935, Tmax = 0.965

  • 3664 measured reflections

  • 1092 independent reflections

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

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.091

  • S = 1.07

  • 1092 reflections

  • 118 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3i 0.83 (3) 1.78 (3) 2.608 (3) 177 (3)
O3-H3...O4ii 0.86 (3) 1.90 (3) 2.756 (2) 175 (3)
O4-H4...O1iii 0.83 (3) 2.39 (3) 3.007 (3) 131 (3)
O4-H4...O2 0.83 (3) 2.20 (3) 2.789 (3) 128 (3)
C5-H5A...O1iv 0.97 2.60 3.511 (3) 157
Symmetry codes: (i) x-1, y-1, z-1; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5819 ).


Acknowledgements

SHH and JR acknowledge financial support by the Higher Education Commission, Pakistan, under its Indigenous 5000 PhD scheme.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Mallesha, L., Mohana, K. N. & Narayana, B. (2009). J. Chem. Crystallogr. 39, 777-780.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Vasudev, P. G., Rai, R., Shamala, N. & Balaram, P. (2008). Biopolymers, 90, 138-150.  [ISI] [PubMed] [ChemPort]


Acta Cryst (2011). E67, o968  [ doi:10.1107/S1600536811010397 ]

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