6-Phenyl-5a,6,6a,7,12,13a-hexa­hydro-5H-benzo[6,7]indolizino[3,2-a]pyrrolizine

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

doi:10.1107/S1600536809020091

. 2009 Jun 6;65(Pt 7):o1454. doi: 10.1107/S1600536809020091

6-Phenyl-5a,6,6a,7,12,13a-hexahydro-5H-benzo[6,7]indolizino[3,2-a]pyrrolizine

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

PMCID: PMC2969265 PMID: 21582758

Abstract

In the title compound, C₂₃H₂₂N₂, the central pyrrolidine ring adopts an envelope conformation. The benzene ring of the hexahydropyrroloisoquinoline ring system makes dihedral angles of 83.43 (6) and 61.99 (10)°, respectively, with the phenyl and pyrrole rings. In the crystal structure, weak C—H⋯π interactions are observed.

Related literature

For biological activity of pyrrolidine derivatives, see: Witherup et al. (1995 ▶); Kravchenko et al. (2005 ▶). For biological activity of pyrrole derivatives, see: Sobral & Rocha Gonsalves (2001a ▶,b ▶); Brockmann & Tour (1995 ▶); Suslick et al. (1992 ▶); Di Natale et al. (1998 ▶). For a related structure, see: Liu et al. (2007 ▶).

Experimental

Crystal data

C₂₃H₂₂N₂
M _r = 326.43
Monoclinic,
a = 14.0694 (14) Å
b = 5.9300 (5) Å
c = 21.177 (2) Å
β = 104.563 (3)°
V = 1710.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.985, T _max = 0.989
20373 measured reflections
4266 independent reflections
3049 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.149
S = 1.01
4266 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020091/is2422sup1.cif

e-65-o1454-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020091/is2422Isup2.hkl

e-65-o1454-Isup2.hkl^{(204.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg3ⁱ	0.93	2.88	3.7250 (3)	152
C13—H13⋯Cg3ⁱⁱ	0.93	2.94	3.5626 (3)	126
C18—H18B⋯Cg6ⁱⁱⁱ	0.97	2.79	3.6726 (4)	152

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg3 and Cg6 are the centroids of the N2/C19–C22 and C11–C16 rings, respectively.

Acknowledgments

The authors thank AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

Pyrrolidine containing compounds are of significant importance because of their biological activities and widespread employment in catalysis (Witherup et al., 1995; Kravchenko et al., 2005). Pyrroles are very useful precursors in porphyrin synthesis (Sobral & Rocha Gonsalves, 2001a,b) and as monomers for polymer chemistry (Brockmann & Tour, 1995), with applications ranging from non linear optical materials (Suslick et al., 1992) to electronic noses (Di Natale et al., 1998).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Liu et al., 2007). The phenyl ring (C11—C16) makes a dihedral angle of 83.43 (6)° with C2—C7 ring and 48.72 (6)° with N2/C19—C22 ring, respectively. The sum of the bond angles around N1 [334.71 (32)°] indicate the sp³ hybridized state of atom N1 in the molecule. The pyrrolidine ring [N1/C9/C10/C17/C23] adopts an envelope conformation.

The crystal structure is stabilized by weak C—H···π [C4—H4···Cg3, C13—H13···Cg3 & C18—H18B···Cg6 (Table 1; Cg3 and Cg6 are the centroid of the rings defined by the atoms N2/C19–C22 and C11–C16, respectively.)] interactions.

Experimental

A mixture of N-allyl pyrrole-2-carbaldehyde (1 mmol) and 1,2,3,4-tetrahydroisoquinolinic acid (1 mmol) was refluxed in 1,2-dichloro benzene (10 ml) for 12 h till the completion of the reaction as evidenced by TLC analysis. The crude mixture was subjected to column chromatography to get the pure product.