(IUCr) 3,5-Dichlorosalicylaldehyde

Volume 64
Part 5
Page o917
May 2008

Received 19 March 2008
Accepted 20 April 2008
Online 26 April 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.101
Data-to-parameter ratio = 16.1
Details

3,5-Dichlorosalicylaldehyde

Isha Azizul ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The title compound (systematic name: 3,5-dichloro-2-hydroxybenzaldehyde), C₇H₄Cl₂O₂, crystallizes as discrete molecules, the conformation of which may be influenced by an intramolecular hydroxy-carbonyl O-HO hydrogen bond.

Related literature

For the crystal structure of 3',5'-dichloroacetophenone, see: Filarowski et al. (2004).

Experimental

Crystal data

C₇H₄Cl₂O₂
M_r = 191.00
Monoclinic, P 2₁ /c
a = 8.2823 (2) Å
b = 13.7412 (3) Å
c = 7.0973 (2) Å
= 115.185 (2)°
V = 730.95 (3) Å³
Z = 4
Mo K radiation
= 0.82 mm^-1
T = 100 (2) K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.701, T_max = 0.960
8436 measured reflections
1672 independent reflections
1303 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.101
S = 1.05
1672 reflections
104 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.59 e Å^-3
_min = -0.49 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2	0.84 (1)	1.87 (2)	2.628 (3)	149 (3)

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2606 ).

Acknowledgements

We thank the University of Malaya for the purchase of the diffractometer.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Filarowski, A., Koll, A., Kochel, A., Kalenik, J. & Hansen, P. E. (2004). J. Mol. Struct. 700, 67-72.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds