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Volume 65 
Part 3 
Page o479  
March 2009  

Received 17 December 2008
Accepted 12 January 2009
Online 6 February 2009

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.061
wR = 0.149
Data-to-parameter ratio = 19.9
Details
Open access

(Cyclopentane-1,1-diyl)dimethanol

aLudwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13 (Haus D), 81377 München, Germany
Correspondence e-mail: kluef@cup.uni-muenchen.de

In the title compound, C7H14O2, co-operative eight-membered homodromic rings of O-H...O hydrogen bonds connect the molecules into strands along [100]. According to graph-set analysis, the descriptor of these cycles is R44(8). The cyclopentane-ring adopts an envelope conformation (C4E).

Related literature

The compound was synthesized according to a published procedure (Domin et al., 2005[Domin, D., Benito-Garagorri, D., Mereiter, K., Froehlich, J. & Kirchner, K. (2005). Organometallics, 24, 3957-3965.]). For the influence of chelation to (semi-)metals on the geometry of bifunctional alcohols, see: Klüfers & Vogler (2007[Klüfers, P. & Vogler, C. (2007). Z. Anorg. Allg. Chem. 633, 908-912.]). For the structure of a related compound, see Wender et al. (1999[Wender, P. A., Glorius, F., Husfeld, C. O., Langkopf, E. & Love, J. A. (1999). J. Am. Chem. Soc. 121, 5348-5349.]). For details on graph-set analysis of hydrogen bonds, see Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For details of puckering analysis, see Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C7H14O2

  • Mr = 130.18

  • Monoclinic, P 21 /n

  • a = 5.8614 (16) Å

  • b = 10.631 (3) Å

  • c = 11.917 (3) Å

  • [beta] = 98.33 (2)°

  • V = 734.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 200 (2) K

  • 0.20 × 0.17 × 0.06 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer

  • Absorption correction: none

  • 4224 measured reflections

  • 1692 independent reflections

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

  • Rint = 0.067

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.149

  • S = 1.01

  • 1692 reflections

  • 85 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.84 1.91 2.720 (2) 163
O2-H2...O1ii 0.84 1.88 2.691 (2) 161
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2005[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2005[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2170 ).


Acknowledgements

The authors thank Professor Klapötke for generous allocation of diffractometer time and Sandra Albrecht for professional support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Domin, D., Benito-Garagorri, D., Mereiter, K., Froehlich, J. & Kirchner, K. (2005). Organometallics, 24, 3957-3965.  [CSD] [CrossRef] [ChemPort]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Klüfers, P. & Vogler, C. (2007). Z. Anorg. Allg. Chem. 633, 908-912.
Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wender, P. A., Glorius, F., Husfeld, C. O., Langkopf, E. & Love, J. A. (1999). J. Am. Chem. Soc. 121, 5348-5349.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2009). E65, o479  [ doi:10.1107/S1600536809001330 ]

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