1′-(4-Bromo­phen­yl)-4′-{4-[(2-oxo-1,2,3,4-tetra­hydro­naphthalen-2-yl­idene)meth­yl]phen­yl}-3′′,4′′-dihydro­acenaphthylene-1-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-2,1′′(1H,2′′H)-dione

B Saravanan; R Rajesh; R Raghunathan; G Chakkaravarthi; V Manivannan

doi:10.1107/S1600536810040171

. 2010 Oct 13;66(Pt 11):o2801. doi: 10.1107/S1600536810040171

1′-(4-Bromophenyl)-4′-{4-[(2-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]phenyl}-3′′,4′′-dihydroacenaphthylene-1-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-2,1′′(1H,2′′H)-dione

B Saravanan ^a, R Rajesh ^b, R Raghunathan ^b, G Chakkaravarthi ^c, V Manivannan ^d,^*

PMCID: PMC3009035 PMID: 21588996

Abstract

In the title compound, C₄₇H₃₄BrNO₃, the central benzene ring makes a dihedral angle of 42.71 (7)° with the bromophenyl ring. The pyrrolidine ring adopts an envelope conformation. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions and the crystal packing is stabilized by weak intermolecular C—H⋯π interactions.

Related literature

For the biological activity of pyrrolidine derivatives, see: Amalraj et al. (2003 ▶); Daly et al. (1986 ▶). For related structures, see: Aravindan et al. (2004 ▶); Kumar et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₄₇H₃₄BrNO₃
M _r = 740.38
Triclinic,
a = 8.4178 (2) Å
b = 13.2352 (3) Å
c = 15.9610 (3) Å
α = 98.143 (1)°
β = 92.744 (2)°
γ = 100.944 (1)°
V = 1723.17 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.24 mm⁻¹
T = 295 K
0.20 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.719, T _max = 0.779
30711 measured reflections
6410 independent reflections
4539 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.098
S = 1.03
6410 reflections
469 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.53 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/S1600536810040171/is2611sup1.cif

e-66-o2801-sup1.cif^{(31.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040171/is2611Isup2.hkl

e-66-o2801-Isup2.hkl^{(307.4KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C3–C8 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22B⋯O3	0.97	2.55	3.026 (3)	111
C23—H23B⋯O3	0.97	2.40	3.113 (3)	130
C17—H17⋯Cg1ⁱ	0.93	2.98	3.720 (3)	137
C26—H26⋯Cg2ⁱⁱ	0.93	3.00	3.925 (3)	178

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge the IIT, Madras, for the data collection.

supplementary crystallographic information

Comment

Highly substituted pyrrolidines have gained much prominence since they form the central skeleton of many natural products (Daly et al., 1986). Substituted pyrrolidine compounds possess antimicrobial and antifungal activities against various pathogens (Amalraj et al., 2003).

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Aravindan et al., 2004; Kumar et al., 2006). The benzene ring (C12–C17) makes a dihedral angle of 42.71 (7)° with the bromophenyl ring (C42–C46). The sum of bond angles around N1 [359.9 (2)°] indicates that N1 is sp²-hybridized.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π [C17—H17···Cg1 (-1 + x, y, z) distance of 3.720 (3)Å and C26—H26···Cg2 (2 - x, -y, -z) distance of 3.925 (3)Å (Cg1 and Cg2 are the centroid of the rings defined by the atoms C3–C8 and C12–C17, respectively) interactions. The intramolecular interactions C22—H22B···O3 and C23—H23B···O3 generate S(6) and S(7) graph set motifs, respectively (Bernstein et al., 1995).

Experimental

To the solution of acenaphthequinone (3) (1.1 mmol), N-(p-bromo) phenyl glycine (2) (1.1 mmol) and 1,4-bis(3',4'-dihydro-1'- oxonaphthalen-2'-ylidene)benzene (1) (1.0 mmol) was refluxed in dry toluene. Completion of the reaction was evidenced by TLC analysis. The solvent was then removed in vacuum, diluted in dichloromethane, washed with water, and brine. The organic layer was separated and dried over Na₂SO₄.The organic solvent was removed and the residue was subjected to column chromatography using hexane/ethyl acetate (6:4) as eluent afforded the cycloadduct.