(IUCr) 2-Formyl-3-hydroxy-9,10-anthroquinone

Volume 64
Part 11
Page o2164
November 2008

Received 23 September 2008
Accepted 6 October 2008
Online 22 October 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.006 Å
R = 0.087
wR = 0.343
Data-to-parameter ratio = 14.0
Details

2-Formyl-3-hydroxy-9,10-anthroquinone

Nor Hadiani Ismail,^a Che Puteh Osman,^a Khalijah Awang,^b Sri Nurestri Abdul Malek ^c and Seik Weng Ng ^b ^*

^aFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Malaysia,^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cInstitute of Biological Sciences, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The molecule of the title compound, C₁₅H₈O₄, is approximately planar. An intramolecular O-HO hydrogen bond is observed between the hydroxy and formyl groups. The crystal used was a nonmerohedral twin, with a minor twin component of 15.9%.

Related literature

For antileshmanial and antiplasmodial activities, see: Sittie et al. (1999). For the treatment of twinned diffraction data, see: Spek (2003).

Experimental

Crystal data

C₁₅H₈O₄
M_r = 252.21
Triclinic, $[P \overline 1]$
a = 6.9194 (2) Å
b = 8.0650 (2) Å
c = 10.7601 (3) Å
= 86.250 (2)°
= 83.214 (2)°
= 64.692 (2)°
V = 538.96 (3) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 100 (2) K
0.22 × 0.04 × 0.04 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: none
4946 measured reflections
2419 independent reflections
1880 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.087
wR(F²) = 0.343
S = 1.11
2419 reflections
173 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O1	0.84	2.00	2.635 (5)	132

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: CI2681 ).

Acknowledgements

The authors thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sittie, A. A., Lemnmich, E., Olsen, C. E., Hviid, L., Kharazmi, A., Nkrumah, F. K. & Christensen, S. B. (1999). Planta Med. 65, 259-261.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds