4-Meth­oxy-5-[4-(4-meth­oxy-1,3-benzodioxol-5-yl)perhydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole

Ezhilmuthu, R.P.; Vembu, N.; Sulochana, N.

doi:10.1107/S1600536808018138

Volume 64
Part 7
Pages o1306-o1307
July 2008

Received 7 June 2008
Accepted 15 June 2008
Online 19 June 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.041
wR = 0.111
Data-to-parameter ratio = 6.5
Details

4-Methoxy-5-[4-(4-methoxy-1,3-benzodioxol-5-yl)perhydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole

Rukmani Perumal Ezhilmuthu,^a Nagarajan Vembu ^b ^* and Nagarajan Sulochana ^c

^aDepartment of Pharmaceutics, Padmavathi College of Pharmacy, Dharmapuri 635 205, India,^bDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India, and ^cDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India
Correspondence e-mail: vembu57@yahoo.com

The 1,3-benzodioxole ring systems in the title compound, C₂₂H₂₂O₈, are almost planar. The perhydrofurofuranyl system linking them adopts a distorted double-envelope conformation. Supramolecular aggregation is effected by C-HO, C-H [pi] and [pi] - [pi] [centroid-centroid distance of 3.755 Å, interplanar distance of 3.633 Å and dihedral angle of 14.6°] interactions.

Related literature

For related literature, see: Fu et al. (2006); Sonar et al. (2006); Hu et al. (2007); Zhou et al. (2007); Liang (2004); Wang et al. (2004); Zheng et al. (2005a,b); Hu et al. (2005); Qi et al. (2006); Hussain et al. (2006); Yu et al. (2006); Zhang et al. (2007); Betz et al. (2007); Yin et al. (2007); Beroza & Barthel (1957); Mitscher et al. (1979); Chien & Cheng (1970); Rao et al. (1981). For hydrogen bonds, see: Desiraju & Steiner (1999); Desiraju (1989). For graph-set notations, see: Bernstein et al. (1995); Etter (1990). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₂H₂₂O₈
M_r = 414.40
Monoclinic, P 2₁
a = 4.754 (5) Å
b = 13.982 (4) Å
c = 14.672 (5) Å
= 97.97 (6)°
V = 965.8 (10) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 293 (2) K
0.3 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.805, T_max = 0.999
2000 measured reflections
1777 independent reflections
1505 reflections with I > 2(I)
R_int = 0.009
2 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.110
S = 1.05
1777 reflections
272 parameters
1 restraint
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.20 e Å^-3

Table 1
Selected torsion angles (°)

O2-C7-C8-C9	-13.3 (3)
C7-C8-C9-C10	-10.7 (3)
C11-C8-C9-C12	-9.0 (3)
C8-C9-C10-O2	32.0 (3)
C9-C8-C11-O1	-11.5 (3)
C8-C9-C12-O1	26.4 (3)

Table 2
Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C1-C6 ring and Cg6 is the centroid of the C13-C18 ring.

D-HA	D-H	HA	DA	D-HA
C5-H5O2	0.93	2.34	2.721 (5)	104
C9-H9O3	0.98	2.48	2.997 (4)	113
C11-H11BO4	0.97	2.56	3.042 (5)	111
C14-H14O1	0.93	2.45	2.808 (5)	103
C19-H19CO7	0.96	2.41	3.065 (6)	125
C20-H20BO5	0.96	2.33	2.939 (7)	121
C7-H7Cg5ⁱ	0.98	2.85	3.724	148
C22-H22ACg6ⁱⁱ	0.97	2.97	3.646	128
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: CAD-4 Software (Enraf-Nonius, 1994); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2355 ).

Acknowledgements

NV thanks Dr Frank R. Fronczek, Department of Chemistry, Louisiana State University, Baton Rouge, USA, for discussions. RPE thanks Mr P. Perumal and Mr M. K. Senthilkumar, JKK Natarajah College of Pharmacy, Komarapalayam, Namakkal District, Tamil Nadu, India, for their help with the IR and HPLC experiments and extraction of the title compound from plant sources, respectively.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Beroza, M. & Barthel, W. F. (1957). J. Agr. Food. Chem. 5, 855-859.
Betz, R., Klüfers, P. & Reichvilser, M. M. (2007). Acta Cryst. E63, o3769.
Chien, P.-L. & Cheng, C. C. (1970). J. Med. Chem. 13, 867-870.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1357-1358.
Desiraju, G. R. (1989). Crystal Engineering: The Design of Organic Solids. Amsterdam: Elsevier.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Fu, X.-S., Zhang, Y., Sun, J.-W. & Yu, X.-X. (2006). Acta Cryst. E62, o3135-o3136.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Hu, S. L., She, N.-F. & Wu, A.-X. (2005). Acta Cryst. E61, o3317-o3318.
Hu, Z.-Q., Zheng, L., Li, C.-J. & Chang, J.-B. (2007). Acta Cryst. E63, o156-o157.
Hussain, M., Ali, S., Altaf, M. & Stoeckli-Evans, H. (2006). Acta Cryst. E62, o5323-o5325.
Liang, Z.-P. (2004). Acta Cryst. E60, o339-o340.
Mitscher, A. L., Flynn, L. D., Gracey, E. H. & Drake, D. S. (1979). J. Med. Chem. 22, 1354-1357.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Qi, X.-X., Suo, J.-S., Wang, L.-M., Guo, X.-H. & Cheng, S.-X. (2006). Acta Cryst. E62, o1269-o1270.
Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421-425.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sonar, V. N., Venkataraj, M., Parkin, S. & Crooks, P. A. (2006). Acta Cryst. E62, o5742-o5744.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Wang, L.-W., Chen, T., Sun, H.-X., Xiong, Y., Zhou, C.-X. & Zhao, Y. (2004). Acta Cryst. E60, o513-o514.
Yin, Z.-G., Qian, H.-Y., Jie, H. & Yu-Li, F. (2007). Acta Cryst. E63, o4406.
Yu, Z.-F., Li, J. & Zhao, Z.-M. (2006). Acta Cryst. E62, o5614-o5615.
Zhang, L., Wang, S.-Q. & Yu, X. (2007). Acta Cryst. E63, o2278-o2279.
Zheng, L., Guo, B., Zheng, X., Chen, J. & Chang, J. (2005a). Acta Cryst. E61, o2508-o2509.
Zheng, L., Zhen, X. F., Zhang, D. & Chang, J. B. (2005b). Acta Cryst. E61, o3786-o3787.
Zhou, Q.-L., Wang, C.-L. & Jing, Z.-L. (2007). Acta Cryst. E63, o898-o899.

organic compounds