10-Phenyl-6b,7,8,9,9a,10-hexa­hydro-6H-cyclo­penta­[4,5]pyrano[3,2-c]chromen-6,9-dione

Qiao, Z.; Liu, L.; Wang, D.

doi:10.1107/S1600536811006192

Volume 67
Part 4
Page o855
April 2011

Received 13 February 2011
Accepted 18 February 2011
Online 12 March 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.055
wR = 0.144
Data-to-parameter ratio = 16.0
Details

10-Phenyl-6b,7,8,9,9a,10-hexahydro-6H-cyclopenta[4,5]pyrano[3,2-c]chromen-6,9-dione

Zhen Qiao,^a Li Liu ^a ^* and Dong Wang ^a

^aBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China
Correspondence e-mail: lliu@iccas.ac.cn

In the title compound, C₂₁H₁₆O₄, the dihedral angle between the phenyl ring and the 2H-chromene ring system is 59.8 (2)°. The crystal packing is stabilized by weak [pi] - [pi] stacking interactions [centroid-centroid distances = 3.667 (2) Å] and intermolecular C-HO hydrogen-bonding interactions.

Related literature

For applications of coumarin, see: Vu et al. (2008); Maresca et al. (2009); Maresca et al. (2010). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₁H₁₆O₄
M_r = 332.34
Monoclinic, P 2₁ /n
a = 9.1672 (14) Å
b = 8.6538 (14) Å
c = 19.899 (3) Å
= 91.295 (3)°
V = 1578.2 (4) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 173 K
0.50 × 0.50 × 0.41 mm

Data collection

Rigaku Saturn724+ CCD diffractometer
Absorption correction: numerical (CrystalClear; Rigaku, 2007) T_min = 0.953, T_max = 0.961
13128 measured reflections
3608 independent reflections
3469 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.144
S = 1.10
3608 reflections
226 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8AO3ⁱ	1.00	2.45	3.4042 (19)	160
C17-H17AO2ⁱⁱ	0.95	2.54	3.322 (2)	140
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2800 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Maresca, A., Temperini, C., Pochet, L., Masereel, B., Scozzafava, A. & Supuran, C. T. (2010). J. Med. Chem. 53, 335-344.
Maresca, A., Temperini, C., Vu, H., Pham, N. B., Poulsen, S. A., Scozzafava, A., Quinn, R. J. & Supuran, C. T. (2009). J. Am. Chem. Soc. 131, 3057-3062.
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vu, H., Pham, N. B. & Quinn, R. J. (2008). J. Biomol. Screen. 13, 265-275.

organic compounds