1′-(1,3-Diphenyl-1H-pyrazol-4-yl)-1′′-methyl-2′,3′,5′,6′,7′,7a'-octa­hydro-1′H-dispiro­[1-benzopyran-3,2′-pyrrolizine-3′,3′′-indoline]-2′′,4-dione

Jagadeesan, G.; Sethusankar, K.; Kathirvelan, D.; Haribabu, J.; Reddy, B.S.R.

doi:10.1107/S1600536813002043

Volume 69
Part 3
Page o317
March 2013

Received 18 December 2012
Accepted 21 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.055
wR = 0.166
Data-to-parameter ratio = 23.0
Details

1'-(1,3-Diphenyl-1H-pyrazol-4-yl)-1''-methyl-2',3',5',6',7',7a'-octahydro-1'H-dispiro[1-benzopyran-3,2'-pyrrolizine-3',3''-indoline]-2'',4-dione

G. Jagadeesan,^a K. Sethusankar,^b ^* D. Kathirvelan,^c J. Haribabu ^c and B. S. R. Reddy ^c

^aDepartment of Physics, Meenakshi College of Engineering, West K.K. Nagar, Chennai 600 078, India,^bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^cIndustrial Chemistry Lab, Central Leather Research Institute, Adyar, Chennai 600 020, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound C₃₈H₃₂N₄O₃, one pyrrolidine ring adopts an envelope conformation with the N atom as the flap while other pyrrolidine ring adopts an twisted conformation. The pyrrolizine ring forms dihedral angles of 79.24 (5) and 77.57 (5)° with the chromene and indole rings, respectively. The carbonyl O atoms deviate from the least-square planes through the chromene and indole rings by 0.0113 (12) and 0.0247 (12) Å, respectively. In the crystal, non-classical C-HO interactions link the molecules, generating an C(9) chain along the b-axis direction.

Related literature

For the biological activity of pyrazole derivatives, see: Mahajan et al. (1991); Baraldi et al. (1998); Katayama & Oshiyama (1997); Chen & Li (1998). For a related structure, see: Fun et al. (2011). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₃₈H₃₂N₄O₃
M_r = 592.68
Triclinic, $[P \overline 1]$
a = 10.8240 (3) Å
b = 10.8382 (3) Å
c = 13.9127 (4) Å
= 70.290 (1)°
= 88.946 (2)°
= 73.578 (1)°
V = 1468.47 (7) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.975, T_max = 0.983
35301 measured reflections
9340 independent reflections
5865 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.166
S = 1.06
9340 reflections
406 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C34-H33O3ⁱ	0.93	2.59	3.523 (3)	178
Symmetry code: (i) x, y+1, z.

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; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2391 ).

Acknowledgements

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

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572-576.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Fun, H.-K., Chia, T. S., Malladi, S., Isloor, A. M. & Shivananda, K. N. (2011). Acta Cryst. E67, o2822-o2823.
Katayama, H. & Oshiyama, T. (1997). Can. J. Chem. 75, 913-919.
Mahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245-249.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds