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

Arfan, M.; Hussain, S.H.; Tahir, M.N.; Rafique, J.; Shaheen, F.

doi:10.1107/S1600536811010397

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 (C-C) = 0.003 Å
R = 0.037
wR = 0.091
Data-to-parameter ratio = 9.3
Details

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

Mohammad Arfan,^a Syed Hamid Hussain,^a M. Nawaz Tahir,^b ^* Jamal Rafique ^a and Farzana Shaheen ^c

^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-HO hydrogen bond generates an S(6) ring with an envelope conformation. In the crystal, molecules are linked by O-HO hydrogen bonds, resulting in R₃³(20) ring motifs and C(2) O-HO-HO-H chains. Overall, a three-dimensional polymeric network arises. A C-HO contact is also present.

Related literature

For related structures, see: Jasinski et al. (2009); Vasudev et al. (2008). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₈H₁₄O₄
M_r = 174.19
Triclinic, P 1
a = 5.7301 (4) Å
b = 6.3493 (3) Å
c = 6.4964 (4) Å
= 92.863 (2)°
= 97.223 (1)°
= 108.258 (2)°
V = 221.67 (2) Å³
Z = 1
Mo K radiation
= 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) T_min = 0.935, T_max = 0.965
3664 measured reflections
1092 independent reflections
932 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(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
_max = 0.22 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O3ⁱ	0.83 (3)	1.78 (3)	2.608 (3)	177 (3)
O3-H3O4ⁱⁱ	0.86 (3)	1.90 (3)	2.756 (2)	175 (3)
O4-H4O1ⁱⁱⁱ	0.83 (3)	2.39 (3)	3.007 (3)	131 (3)
O4-H4O2	0.83 (3)	2.20 (3)	2.789 (3)	128 (3)
C5-H5AO1^iv	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) 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.
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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Mallesha, L., Mohana, K. N. & Narayana, B. (2009). J. Chem. Crystallogr. 39, 777-780.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vasudev, P. G., Rai, R., Shamala, N. & Balaram, P. (2008). Biopolymers, 90, 138-150.