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

Kailani, M.H.

doi:10.1107/S1600536813000366

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 (C-C) = 0.005 Å
R = 0.038
wR = 0.085
Data-to-parameter ratio = 14.5
Details

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

Mohammed H. Kailani ^a ^*

^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-HO hydrogen bonds. The overall three-dimesional supramolecular architecture is stabilized by C-ClO halogen bonding, with a ClO separation of 3.139 (3) Å and a C-ClO angle of 162.5 (2)°.

Related literature

For background on this class of compounds, see: Kean et al. (2012); Lenhardt et al. (2009). For one-handed helical chains caused by hydrogen bonds, see: Abe et al. (2012). For the preparation of this type of compound, see: Kailani et al. (2012); Pustovit et al. (1994).

Experimental

Crystal data

C₅H₈Cl₂O₂
M_r = 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 radiation
= 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) T_min = 0.91, T_max = 0.96
6911 measured reflections
2628 independent reflections
1969 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(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
_max = 0.17 e Å^-3
_min = -0.17 e Å^-3
Absolute structure: Flack (1983), 1081 Friedel pairs
Flack parameter: 0.03 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1A-H4O2Bⁱ	0.76 (3)	1.89 (3)	2.650 (4)	174 (4)
O2B-H3O2Aⁱⁱ	0.84 (4)	1.84 (4)	2.668 (4)	171 (4)
O2A-H2O1B	0.78 (4)	1.90 (4)	2.678 (4)	174 (4)
O1B-H1O1Aⁱⁱⁱ	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); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); 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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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.
Lenhardt, J. M., Black, A. L. & Craig, S. L. (2009). J. Am. Chem. Soc. 131, 10818-10819.
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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds