3-Acetyl-5-hy­droxy-2-methyl­anthra[1,2-b]furan-6,11-dione

Ahmad, R.; Jeinie, M.F.; Ismail, N.H.; Hazni, H.; Ng, S.W.

doi:10.1107/S1600536811013389

Volume 67
Part 5
Page o1144
May 2011

Received 4 April 2011
Accepted 10 April 2011
Online 16 April 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.006 Å
R = 0.068
wR = 0.149
Data-to-parameter ratio = 11.0
Details

3-Acetyl-5-hydroxy-2-methylanthra[1,2-b]furan-6,11-dione

Rohaya Ahmad,^a Mohamad Faiz Jeinie,^a Nor Hadiani Ismail,^a Hazrina Hazni ^b and Seik Weng Ng ^b ^*

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

The asymmetric unit of the title compound, C₁₉H₁₂O₅, contains two independent molecules, both slightly buckled along an axis passing through the C=O bonds of the anthraquinone ring system (r.m.s. deviation of non-H atoms = 0.082 and 0.148 Å): the benzene rings are twisted to each other by 4.3 (3)°in one molecule and 10.6(3)° in the other. In both molecules, the hydroxy group forms an intramolecular O-HO hydrogen bond. The two independent molecules interact by [pi] - [pi] stacking with a centroid-centroid distance of 3.539 (2) Å between hydroxybenzene rings of adjacent molecules.

Related literature

For background to the synthesis, see: Boddy et al. (1986).

Experimental

Crystal data

C₁₉H₁₂O₅
M_r = 320.29
Monoclinic, P 2₁ /c
a = 12.5739 (9) Å
b = 22.0375 (12) Å
c = 10.7453 (8) Å
= 110.342 (8)°
V = 2791.8 (3) Å³
Z = 8
Mo K radiation
= 0.11 mm^-1
T = 100 K
0.35 × 0.05 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.962, T_max = 0.998
12061 measured reflections
4905 independent reflections
2305 reflections with I > 2(I)
R_int = 0.093

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.149
S = 0.95
4905 reflections
445 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O5-H5O4	0.84 (1)	1.82 (2)	2.596 (4)	153 (4)
O10-H10O9	0.84 (1)	1.77 (3)	2.552 (4)	153 (6)

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5188 ).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Boddy, I. K., Cambie, R. C., Rutledge, P. S. & Woodgate, P. D. (1986). Aust. J. Chem. 39, 2075-2088.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds