Ethyl 7′-(6-benz­yloxy-2,2-dimethyl­tetra­hydro­furo[3,2-d][1,3]dioxol-5-yl)-2-oxo-5′,6′,7′,7a'-tetra­hydro-1′H,2H-spiro­[acenaphthyl­ene-1,5′-pyrrolo­[1,2-c][1,3]thia­zole]-6′-carboxyl­ate

Jagadeesan, G.; Sethusankar, K.; Prasanna, R.; Raghunathan, R.

doi:10.1107/S1600536812032291

Volume 68
Part 8
Pages o2505-o2506
August 2012

Received 2 July 2012
Accepted 16 July 2012
Online 21 July 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.037
wR = 0.083
Data-to-parameter ratio = 13.7
Details

Ethyl 7'-(6-benzyloxy-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl)-2-oxo-5',6',7',7a'-tetrahydro-1'H,2H-spiro[acenaphthylene-1,5'-pyrrolo[1,2-c][1,3]thiazole]-6'-carboxylate

G. Jagadeesan,^a K. Sethusankar,^b ^* R. Prasanna ^c and R. Raghunathan ^c

^aDepartment of Physics, Dr MGR Educational and Research Institute, Dr MGR University, Chennai 600 095, India,^bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C₃₄H₃₅NO₇S, the acenaphthylene unit is essentially planar (r.m.s. deviation = 0.0335 Å). The pyrrolothiazole ring system is folded about the bridging N-C bond; the thiazolidine and pyrrolidine rings adopt S- and C-envelope conformations, respectively, with a `butterfly' angle between the mean planes of 51.38 (10)°. The dioxolane and tetrahydrofuran rings adopt O- and a C-envelope conformations, respectively, with a `butterfly' angle between the mean planes of 57.12 (10)°. Two C atoms are each disordered over two positions with site-occupancy factors of 0.450 (7) and 0.550 (7). The crystal packing is stabilized by C-HO interactions, generating an R₂²(14) graph-set ring motif.

Related literature

For the biological properties of spiroheterocycles, see: Kilonda et al. (1995); Ferguson et al. (2005). For a related structure, see: Jagadeesan et al. (2012). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₃₄H₃₅NO₇S
M_r = 601.69
Monoclinic, P 2₁
a = 8.588 (5) Å
b = 20.446 (5) Å
c = 8.851 (5) Å
= 93.282 (5)°
V = 1551.6 (13) Å³
Z = 2
Mo K radiation
= 0.15 mm^-1
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.955, T_max = 0.970
13521 measured reflections
5470 independent reflections
4678 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.083
S = 1.03
5470 reflections
400 parameters
5 restraints
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 2630 Friedel pairs
Flack parameter: 0.04 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O3ⁱ	0.93	2.51	3.375 (4)	155
C17-H17AO7ⁱⁱ	0.97	2.44	3.309 (3)	148
C23-H23FO4ⁱⁱⁱ	0.96	2.57	3.497 (9)	163
C31-H31O5^iv	0.93	2.47	3.393 (4)	173
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (ii) x+1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (iv) x, y, z-1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2565 ).

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Ferguson, N. M., Cummings, D. A. T., Cauchemez, S., Fraser, C., Riley, S., Meeyai, A., Iamsirithaworn, S. & Burke, D. S. (2005). Nature (London), 437, 209-214.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012). Acta Cryst. E68, o382-o383.
Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820-5824.
Sheldrick, G. M. (1996). SADABS. University of Goöttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.