{1′-Phenyl-1′,2′,5′,6′,7′,7a'-hexa­hydro­spiro­[indeno­[1,2-b]quinoxaline-11,3′-pyrrolizin]-2′-yl}(p-tol­yl)methanone

Srinivasan, T.; Suhitha, S.; Purushothaman, S.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536812031480

Volume 68
Part 8
Page o2469
August 2012

Received 25 June 2012
Accepted 10 July 2012
Online 18 July 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.049
wR = 0.144
Data-to-parameter ratio = 18.3
Details

{1'-Phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizin]-2'-yl}(p-tolyl)methanone

T. Srinivasan,^a S. Suhitha,^a S. Purushothaman,^b R. Raghunathan ^b and D. Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C₃₅H₂₉N₃O, the quinoxaline and indene systems are essentially planar, with maximum deviations of 0.047 (2) and 0.032 (2) Å for C atoms, respectively. The quinoxaline system forms a dihedral angle of 4.75 (3)° with the indene system. The pyrrolizine system is folded. The substituted five-membered ring adopts an envelope conformation. In the other five-membered ring, one C atom is disordered with a site-occupancy ratio of 0.676 (12):0.324 (12). In the crystal, molecules are linked via C-HO hydrogen bonds involving the bifurcated carbonyl O atom.

Related literature

For the uses of pyrrolidine and quinoxaline derivatives, see: Amal Raj et al. (2003); Zarranz et al. (2003). For a related structure, see: Gayathri et al. (2005).;

Experimental

Crystal data

C₃₅H₂₉N₃O
M_r = 507.61
Orthorhombic, P b c a
a = 16.4102 (6) Å
b = 16.4371 (6) Å
c = 20.0648 (7) Å
V = 5412.2 (3) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
47718 measured reflections
6643 independent reflections
3751 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.144
S = 1.01
6643 reflections
363 parameters
3 restraints
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1CO1ⁱ	0.96	2.56	3.483 (2)	161
C22-H22O1ⁱⁱ	0.93	2.48	3.361 (3)	158
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008); 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: BT5959 ).

Acknowledgements

TS and DV thank TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for data collection and TS thanks DST for an Inspire fellowship.

References

Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-409.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gayathri, D., Aravindan, P. G., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2005). Acta Cryst. E61, o3124-o3126.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zarranz, B., Jago, A., Aldana, I. & Monge, A. (2003). Bioorg. Med. Chem. 11, 2149-2156.