7′-(2,5-Dimeth­oxy­phen­yl)-1′,3′,5′,6′,7′,7a'-hexa­hydro­dispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione

Wei, A.C.; Ali, M.A.; Choon, T.S.; Razak, I.A.; Arshad, S.

doi:10.1107/S1600536812003169

Volume 68
Part 3
Pages o560-o561
March 2012

Received 16 January 2012
Accepted 25 January 2012
Online 4 February 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.106
Data-to-parameter ratio = 22.5
Details

7'-(2,5-Dimethoxyphenyl)-1',3',5',6',7',7a'-hexahydrodispiro[indan-2,5'-pyrrolo[1,2-c][1,3]thiazole-6',2''-indan]-1,3,1''-trione

Ang Chee Wei,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Ibrahim Abdul Razak ^b ^*⁺ and Suhana Arshad ^b

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

In the title compound, C₃₀H₂₅NO₅S, all the five-membered rings are in envelope conformations with the spiro and methylene C atoms as the flap atoms. Intramolecular C-HO interactions stabilize the molecular structure and form S(6) and S(7) ring motifs. The mean plane through the hexahydropyrrolo[1,2-c]thiazole ring [r.m.s deviation of 0.0393 (1) Å] makes dihedral angles of 60.92 (5), 88.33 (4) and 84.12 (4)° with the terminal benzene ring and the mean planes of the mono and di-oxo substituted indan rings, respectively. Molecules are linked by intermolecular C-HO interactions into a three-dimensional network. In addition, C-H [pi] and [pi] - [pi] interactions [centroid-to-centroid distance = 3.4084 (8) Å] further stabilize the crystal structure.

Related literature

For related structures, see: Wei, Ali, Choon et al. (2011); Wei, Ali, Ismail et al. (2011); Wei, Ali, Yoon et al. (2011). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₃₀H₂₅NO₅S
M_r = 511.57
Triclinic, $[P \overline 1]$
a = 9.0425 (4) Å
b = 11.1127 (5) Å
c = 13.3005 (6) Å
= 68.016 (1)°
= 84.588 (1)°
= 79.735 (1)°
V = 1218.95 (9) Å³
Z = 2
Mo K radiation
= 0.18 mm^-1
T = 100 K
0.36 × 0.19 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.939, T_max = 0.983
27399 measured reflections
7546 independent reflections
6172 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.106
S = 1.03
7546 reflections
336 parameters
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16-C21 ring.

D-HA	D-H	HA	DA	D-HA
C2-H2AO1	0.99	2.58	3.2234 (15)	123
C4-H4AO1	1.00	2.49	3.1289 (15)	122
C22-H22BO2	0.99	2.27	3.0697 (16)	137
C11-H11AO3ⁱ	0.95	2.44	3.1210 (15)	129
C20-H20AO2ⁱⁱ	0.95	2.48	3.1176 (14)	124
C1-H1AO4ⁱⁱⁱ	0.99	2.40	3.2806 (16)	148
C30-H30CO1^iv	0.98	2.47	3.2433 (18)	136
C2-H2BCg1^v	0.99	2.58	3.5224 (14)	160
Symmetry codes: (i) -x, -y+2, -z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z; (v) x+1, y, z.

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: RZ2700 ).

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for Research University grants Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012. The authors are also grateful to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wei, A. C., Ali, M. A., Choon, T. S., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2383.
Wei, A. C., Ali, M. A., Ismail, R., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2381-o2382.
Wei, A. C., Ali, M. A., Yoon, Y. K., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2404.

organic compounds