1,4-Dichloro­naphthalene-2,3-diol

Ahn, P.D.; Bishop, R.; Craig, D.C.; Scudder, M.L.

doi:10.1107/S1600536809004310

Volume 65
Part 3
Page o636
March 2009

Received 2 February 2009
Accepted 5 February 2009
Online 28 February 2009

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.022
wR = 0.034
Data-to-parameter ratio = 7.9
Details

1,4-Dichloronaphthalene-2,3-diol

Paul D. Ahn,^a Roger Bishop,^a Donald C. Craig ^a and Marcia L. Scudder ^a ^*

^aSchool of Chemistry, University of New South Wales, Sydney, Australia 2052
Correspondence e-mail: m.scudder@unsw.edu.au

The achiral planar (maximum deviation 0.014 Å) title compound, C₁₀H₆Cl₂O₂, crystallizes in the chiral space group P2₁2₁2₁ in an arrangement incorporating conventional O-HO hydrogen bonding leading to a supramolecular chain.

Related literature

For related structures, see: Ahn et al. (1995, 1996). For the synthesis, see: Zincke & Fries (1904); Ahn et al. (1995). For related literature, see: Coppens & Hamilton (1970).

Experimental

Crystal data

C₁₀H₆Cl₂O₂
M_r = 229.1
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.0037 (4) Å
b = 11.589 (1) Å
c = 15.546 (2) Å
V = 901.5 (2) Å³
Z = 4
Cu K radiation
= 6.24 mm^-1
T = 294 K
0.32 × 0.09 × 0.09 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: analytical (de Meulenaer & Tompa, 1965) T_min = 0.32, T_max = 0.65
1022 measured reflections
1022 independent reflections
958 reflections with I > 2(I)
1 standard reflections frequency: 30 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.022
wR(F²) = 0.034
S = 1.38
1022 reflections
129 parameters
H-atom parameters not refined
_max = 0.18 e Å^-3
_min = -0.17 e Å^-3
Absolute structure: Flack (1983), no Friedel pairs
Flack parameter: 0.02 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O1O1ⁱ	1.00	2.00	2.977 (3)	165
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Manual (Schagen et al., 1989); cell refinement: CAD-4 Manual; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: local programs.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2370 ).

Acknowledgements

This research was supported by the Australian Research Council.

References

Ahn, P. D., Bishop, R., Craig, D. C. & Scudder, M. L. (1995). J. Incl. Phenom. Mol. Rec. Chem. 20, 267-276.
Ahn, P. D., Bishop, R., Craig, D. C. & Scudder, M. L. (1996). J. Incl. Phenom. Mol. Rec. Chem. 23, 313-327.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Coppens, P. & Hamilton, W. C. (1970). Acta Cryst. A26, 71-83.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.
Rae, A. D. (2000). RAELS. Australian National University, Canberra.
Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Manual. Enraf-Nonius, Delft, The Netherlands.
Zincke, T. & Fries, K. (1904). Annalen, 334, 342-366.

organic compounds