Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

Gunasekaran, B.; Kathiravan, S.; Raghunathan, R.; Renuga, V.; Manivannan, V.

doi:10.1107/S1600536809012914

Volume 65
Part 5
Page o1033
May 2009

Received 30 March 2009
Accepted 5 April 2009
Online 10 April 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.107
Data-to-parameter ratio = 13.7
Details

Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate

B. Gunasekaran,^a S. Kathiravan,^b R. Raghunathan,^b V. Renuga ^c and V. Manivannan ^d ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India,^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India,^cDepartment of Chemistry, National College, Thiruchirapalli, Tamil Nadu, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: manivan_1999@yahoo.com

In the title compound, C₂₄H₂₃NO₃, the dihedral angle between the naphthalene ring system and the phenyl ring is 76.82 (6)°. The pyrrolidine ring adopts an envelope conformation. In the crystal, weak intermolecular C-HO and C-H [pi] interactions are observed.

Related literature

For the biological activity of chromenopyrrole, see: Caine (1993); Tidey (1992); Carlson (1993); Sokoloff et al. (1990); Wilner (1985); Sobral & Rocha Gonsalves (2001a,b); Brockmann & Tour (1995); Suslick et al. (1992); Di Natale et al. (1998). For a related structure, see: Nirmala et al. (2008). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₄H₂₃NO₃
M_r = 373.43
Monoclinic, P 2₁ /n
a = 13.2332 (6) Å
b = 10.3574 (4) Å
c = 15.0865 (6) Å
= 111.530 (2)°
V = 1923.50 (14) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEX2 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.979, T_max = 0.987
19089 measured reflections
3499 independent reflections
2413 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.107
S = 1.02
3499 reflections
255 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15O2ⁱ	0.98	2.53	3.347 (2)	141
C16-H16CCgⁱⁱ	0.96	2.79	3.689 (4)	156
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1. Cg is the centroid of the C4-C9 ring.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2404 ).

Acknowledgements

Author thanks AMET University Management, India, for their kind support.

References

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Sokoloff, P., Giros, B., Martres, M. P., Bouthenet, M. L. & Schwartz, J. C. (1990). Nature (London), 347, 147-151.
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organic compounds