4-Hy­droxy-3-[(4-hy­droxy-2-oxo-2H-3-chromen­yl)(3-thien­yl)meth­yl]-2H-chromen-2-one

Asad, M.; Oo, C.-W.; Osman, H.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536811011676

Volume 67
Part 5
Pages o1037-o1038
May 2011

Received 16 March 2011
Accepted 29 March 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean () = 0.000 Å
Disorder in main residue
R = 0.044
wR = 0.106
Data-to-parameter ratio = 10.3
Details

4-Hydroxy-3-[(4-hydroxy-2-oxo-2H-3-chromenyl)(3-thienyl)methyl]-2H-chromen-2-one

Mohammad Asad,^a Chuan-Wei Oo,^a ⁺ Hasnah Osman,^a Mohd Mustaqim Rosli ^b and Hoong-Kun Fun ^b ^*⁺⁺

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The whole molecule of the title compound, C₂₃H₁₄O₆S, is disordered over two sets of sites with refined occupancies of 0.8733 (12):0.1267 (12). The dihedral angle between the mean planes through the chromene ring systems is 56.31 (5) and 55.2 (3)° for the major and minor components, respectively. In both components, a pair of intramolecular O-HO interactions generate rings of S(8) graph-set motif. In the crystal, the molecules are linked by intermolecular C-HO interactions, forming chains along the b axis. The structure is further stabilized by [pi] - [pi] interactions with centroid-centroid distances of 3.594 (2) and 3.608 (5) Å.

Related literature

For the biological activity of 4-hydroxycoumarins, see: Abdelhafez et al. (2010); Huang et al. (2010); Jacquot et al. (2001); Kokil et al. (2010); Siddiqui & Asad (2010); Skulnick et al. (1997); Sullivan et al. (1943). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₃H₁₄O₆S
M_r = 418.40
Monoclinic, P 2₁ /c
a = 7.8225 (2) Å
b = 8.9426 (2) Å
c = 27.1317 (6) Å
= 100.679 (1)°
V = 1865.09 (8) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 297 K
0.49 × 0.44 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.902, T_max = 0.966
20839 measured reflections
5420 independent reflections
3497 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.106
S = 1.02
5420 reflections
524 parameters
252 restraints
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3BO4	0.82	1.89	2.7049 (19)	180
O6-H6BO5	0.82	1.79	2.612 (2)	179
C21-H21AO4ⁱ	0.93	2.56	3.475 (8)	168
O3X-H3XBO4X	0.82	1.86	2.682 (15)	178
O6X-H6XBO5X	0.82	1.69	2.49 (2)	168
C23X-H23BO3Xⁱ	0.93	2.53	3.31 (5)	142
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2575 ).

Acknowledgements

The authors are thankful to Universiti Sains Malaysia (USM) for providing the necessary research facilities and RU research funding under the grant No. 1001/PKIMIA/811134. MA also thanks Universiti Sains Malaysia for the award of post-doctoral fellowship. HKF and MMR thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

References

Abdelhafez, O. M., Amin, K. M., Batran, R. Z., Maher, T. J., Nada, S. A. & Sethumadhavan, S. (2010). Bioorg. Med. Chem. 18, 3371-3378.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
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Huang, W. Y., Cai, Y. Z. & Zhang, Y. (2010). Nutr. Cancer 62, 1-20.
Jacquot, Y., Bermont, L., Giorgi, H., Refouvelet, B., Adessi, G., Daubrosse, E. & Xicluna, A. (2001). Eur. J. Med. Chem. 36, 127-136.
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Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sullivan, W. R., Hubbner, C. F., Stahmann, M. A. & Link, K. P. (1943). J. Am. Chem. Soc. 65, 2288-2291.

organic compounds