4′-(4-Chlorophenyl)-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Ang Chee Wei; Mohamed Ashraf Ali; Yeong Keng Yoon; Ching Kheng Quah; Hoong-Kun Fun

doi:10.1107/S1600536811033642

. 2011 Aug 27;67(Pt 9):o2404. doi: 10.1107/S1600536811033642

4′-(4-Chlorophenyl)-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Ang Chee Wei ^a, Mohamed Ashraf Ali ^a, Yeong Keng Yoon ^a, Ching Kheng Quah ^b,^‡, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC3200810 PMID: 22064509

Abstract

In the title compound, C₂₇H₂₀ClNO₃, the two cyclopentane rings adopt envelope conformations. The pyrrolidine ring also adopts an envelope conformation (with the spiro C atom as the flap) and its least-squares plane (fitted to five atoms) makes dihedral angles of 66.50 (9), 77.36 (8) and 73.76 (8)° with the chlorobenzene ring and the two 2,3-dihydro-1H-indene ring systems, respectively. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into chains running parallel to the [001] direction.

Related literature

For background to the synthesis, see: Amalraj & Raghunathan (2003 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For graph-set descriptors of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Kumar et al. (2010 ▶); Wei, Ali, Choon et al. (2011 ▶); Wei, Ali, Ismail et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₇H₂₀ClNO₃
M _r = 441.89
Monoclinic,
a = 7.8216 (1) Å
b = 21.2865 (3) Å
c = 14.0641 (2) Å
β = 116.156 (1)°
V = 2101.81 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.43 × 0.11 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.913, T _max = 0.979
25402 measured reflections
6459 independent reflections
4537 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.113
S = 1.06
6459 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033642/hb6361sup1.cif

e-67-o2404-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033642/hb6361Isup2.hkl

e-67-o2404-Isup2.hkl^{(316.1KB, 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
C18—H18A⋯O2	0.99	2.40	3.055 (2)	123
C6—H6A⋯O1ⁱ	0.95	2.57	3.244 (2)	128
C14—H14A⋯O3ⁱ	0.95	2.45	3.167 (2)	132

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to express their thanks to Universiti Sains Malaysia (USM), Penang, Malaysia, for providing research facilities. HKF and CKQ also thank USM for a Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

1,3-Dipolar cycloaddition is a very useful synthetic strategy to construct heterocycles in which high regio- and stereo-chemical control of peripheral substituents can be achieved (Amalraj & Raghunathan, 2003). As part of our studies in this area, the title compound, (I), was prepared and it structure is now described.

The molecular structure is shown in Fig. 1. The two cyclopentane rings, C1-C3/C8/C9 and C10-C12/C17/C18, are in envelope conformations, puckering parameters (Cremer & Pople, 1975) Q =0.2239 (17) Å and φ = 177.0 (4)° with atom C1 at the flap; and Q = 0.2121 (17) Å and φ = 355.2 (5)° with atom C10 at the flap, respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Kumar et al., 2010; Wei, Ali, Choon et al. (2011); Wei, Ali, Ismail et al. (2011). The pyrrolidine ring (N1/C1/C10/C19/C20) adopts an envelope conformation, puckering parameters (Cremer & Pople, 1975) Q = 0.4461 (17) Å and φ = 41.6 (2)°, with atom C1 at the flap and its least-squares plane makes dihedral angles of 66.50 (9), 77.36 (8) and 73.76 (8)° with a phenyl ring (C22-C27) and the two least-squares planes of 2,3-dihydro-1H-indene ring system [C1-C9 (maximum deviation of 0.234 (2) Å at atom C1) and C10-C18 (maximum deviation of 0.221 (2) Å at atom C10)], respectively. The molecular structure is stabilized by an intramolecular C18–H18A···O2 hydrogen bond (Table 1), which generates an S(6) ring motif (Fig. 1, Bernstein et al., 1995).

In the crystal (Fig. 2), molecules are linked by C6–H6A···O1 and C14–H14A···O3 hydrogen bonds (Table 1) into one-dimensional chains parallel to [001] direction.

Experimental

A mixture of (E)2-(4-chlorobenzylidene)-2,3-dihydro-1H- indene-1-one (0.001 mmol), ninhydrin (0.001 mmol) and sarcosine (0.002 mmol) (1:1:2) were dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the mixture was poured into water (50 ml). The precipitated solid was filtered, washed with water and recrystallised from pet.ether-ethyl acetate mixture (1:1) to reveal the title compound as yellow crystals.