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Volume 69 
Part 2 
Page o225  
February 2013  

Received 17 December 2012
Accepted 4 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.038
wR = 0.085
Data-to-parameter ratio = 14.5
Details
Open access

[(1R,3S)-2,2-Dichloro-3-(hydroxymethyl)cyclopropyl]methanol

aDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan
Correspondence e-mail: kailani@ju.edu.jo

The title compound, C5H8Cl2O2, represents a meso isomer crystallizing in a chiral space group with two molecules per asymmetric unit. The molecules form helical associates with a pitch of 6.31 Å along the a axis via O-H...O hydrogen bonds. The overall three-dimesional supramolecular architecture is stabilized by C-Cl...O halogen bonding, with a Cl...O separation of 3.139 (3) Å and a C-Cl...O angle of 162.5 (2)°.

Related literature

For background on this class of compounds, see: Kean et al. (2012[Kean, Z. S., Black Ramirez, A. L. & Craig, S. L. (2012). J. Polym. Sci. Part A Polym. Chem. 50, 3481-3484.]); Lenhardt et al. (2009[Lenhardt, J. M., Black, A. L. & Craig, S. L. (2009). J. Am. Chem. Soc. 131, 10818-10819.]). For one-handed helical chains caused by hydrogen bonds, see: Abe et al. (2012[Abe, Y., Aoki, T., Jia, H., Hadano, H., Namikshi, T., Kakihana, Y., Liu, L., Zang, Y., Teraguchi, M. & Kaneko, T. (2012). Molecules, 17, 433-451.]). For the preparation of this type of compound, see: Kailani et al. (2012[Kailani, M. H., Al-Bakri, A. G., Saadeh, H. & Al-Hiari, Y. M. (2012). Jordan J. Chem. 7, 239-252.]); Pustovit et al. (1994[Pustovit, Y. M., Ogojko, P. I., Nazaretian, V. P. & Rozhenko, A. B. (1994). J. Fluorine Chem. 69, 231-236.]).

[Scheme 1]

Experimental

Crystal data
  • C5H8Cl2O2

  • Mr = 171.02

  • Orthorhombic, P 21 21 21

  • a = 6.3110 (13) Å

  • b = 15.429 (3) Å

  • c = 15.433 (3) Å

  • V = 1502.7 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.79 mm-1

  • T = 293 K

  • 0.2 × 0.1 × 0.05 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (COLLECT; Nonius, 2004[Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.]) Tmin = 0.91, Tmax = 0.96

  • 6911 measured reflections

  • 2628 independent reflections

  • 1969 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.085

  • S = 1.03

  • 2627 reflections

  • 181 parameters

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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1081 Friedel pairs

  • Flack parameter: 0.03 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1A-H4...O2Bi 0.76 (3) 1.89 (3) 2.650 (4) 174 (4)
O2B-H3...O2Aii 0.84 (4) 1.84 (4) 2.668 (4) 171 (4)
O2A-H2...O1B 0.78 (4) 1.90 (4) 2.678 (4) 174 (4)
O1B-H1...O1Aiii 0.84 (4) 1.86 (4) 2.680 (5) 167 (4)
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [-x+{\script{5\over 2}}, -y, z+{\script{1\over 2}}]; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2004[Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2090 ).


Acknowledgements

Data were collected by Malva Liu Gonzalez (Universitat València-SCSIE, Carrer del Dr Moliner, 50 Edifici de Investigació, Lab-1.46/-1.51, 46100 Burjassot-València, España).

References

Abe, Y., Aoki, T., Jia, H., Hadano, H., Namikshi, T., Kakihana, Y., Liu, L., Zang, Y., Teraguchi, M. & Kaneko, T. (2012). Molecules, 17, 433-451.  [CrossRef] [ChemPort] [PubMed]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Kailani, M. H., Al-Bakri, A. G., Saadeh, H. & Al-Hiari, Y. M. (2012). Jordan J. Chem. 7, 239-252.
Kean, Z. S., Black Ramirez, A. L. & Craig, S. L. (2012). J. Polym. Sci. Part A Polym. Chem. 50, 3481-3484.  [CrossRef] [ChemPort]
Lenhardt, J. M., Black, A. L. & Craig, S. L. (2009). J. Am. Chem. Soc. 131, 10818-10819.  [ISI] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pustovit, Y. M., Ogojko, P. I., Nazaretian, V. P. & Rozhenko, A. B. (1994). J. Fluorine Chem. 69, 231-236.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o225  [ doi:10.1107/S1600536813000366 ]

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