3-(4-Methoxy­phen­yl)-6-(phenyl­sulfon­yl)perhydro-1,3-thiazolo[3′,4′:1,2]pyrrolo[4,5-c]pyrrole

S Sundaramoorthy; D Gayathri; D Velmurugan; K Ravikumar; M Poornachandran

doi:10.1107/S1600536808002134

. 2008 Jan 25;64(Pt 2):o515. doi: 10.1107/S1600536808002134

3-(4-Methoxyphenyl)-6-(phenylsulfonyl)perhydro-1,3-thiazolo[3′,4′:1,2]pyrrolo[4,5-c]pyrrole

S Sundaramoorthy ^a, D Gayathri ^a, D Velmurugan ^a,^*, K Ravikumar ^b, M Poornachandran ^c

PMCID: PMC2960171 PMID: 21201534

Abstract

In the title compound, C₂₁H₂₄N₂O₃S₂, the three five-membered rings adopt envelope conformations. The dihedral angle between the two aromatic rings is 68.4 (1)°. C—H⋯O interactions link the molecules into a chain and the chains are cross-linked via C—H⋯π interactions involving the methoxyphenyl ring.

Related literature

For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For general background, see: Amal Raj et al. (2003 ▶); Tsuru et al. (1988 ▶). For a related structure, see: Kavitha et al. (2006 ▶).

Experimental

Crystal data

C₂₁H₂₄N₂O₃S₂
M _r = 416.54
Monoclinic,
a = 14.5533 (8) Å
b = 8.3319 (5) Å
c = 16.8828 (9) Å
β = 98.923 (1)°
V = 2022.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 (2) K
0.24 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
22482 measured reflections
4769 independent reflections
3991 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.137
S = 1.00
4769 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002134/ci2542sup1.cif

e-64-0o515-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002134/ci2542Isup2.hkl

e-64-0o515-Isup2.hkl^{(228.9KB, hkl)}

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

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

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1ⁱ	0.93	2.56	3.437 (3)	158
C3—H3⋯Cg1ⁱⁱ	0.98	2.76	3.729 (2)	172

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

Acknowledgments

DG thanks the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship. The University Grants Commission (UGC–SAP) and Department of Science and Technology (DST–FIST), Government of India, are acknowledged by DV for providing facilities to the department.

supplementary crystallographic information

Comment

Substituted pyrrolidine compounds have gained much importance as they are the structural elements of many alkaloids. The pyrrolidine derivatives have been found to possess antifungal activity against various pathogens (Amal Raj et al., 2003). Thiazolidine derivatives may act as potent inhibitors specific for Pro1yl Endopeptidase (Tsuru et al., 1988). In view of the above facts, we have undertaken the X-ray crystal structure determination of the title compound.

Bond lenghts and angles in the title molecule (Fig. 1) are comparable to those observed in a related structure (Kavitha et al., 2006). The sums of the bond angles around N1 (343.7°) and N2 (333.1°) indicate sp³-hybridization. The thiazolidine and the two pyrrolidine rings (N1/C1—C4, A, and C2/C3/N2/C5/C6, B) adopt envelope conformations. Atom N1 in ring A lies 0.597 (2) Å below the C1—C4 mean plane and atom C6 in ring B lies 0.563 (3) Å above the N2/C3/C2/C5 plane. In the thiazolidine ring, atom C6 deviates by 0.554 (3) Å from the plane of the rest of the atoms in the ring. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) are q₂ = 0.406 (2) Å, φ = 187.3 (3)° and Δ_s(N₁) = 6.5 (2)° for ring A, q₂ = 0.372 (2) Å, φ = 137.0 (3)° and Δ_s(C₆) = 4.2 (2)° for ring B, and q₂ = 0.378 (2) Å, φ = 69.8 (3)° and Δ_s(C₆) = 3.7 (2)° for the thiazolidine ring. The dihedral angle between the two aromatic rings is 68.4 (1)°.

The crystal packing is stabilized by C—H···O and C—H···π intermolecular interactions.

Experimental

A mixture of 2-(N-allyl-N-phenylsulfonyl) butanal (1.0 mmol) and of 2-p-methoxyphenylthiazolidine-4-carboxylic acid (1.5 mmol) in dry toluene (30 ml) was refluxed under Dean-Stark conditions till the completion of the reaction (3 h). The reaction mixture was then concentrated under reduced pressure. The residue was extracted with dichloromethane (2× 20 ml) and water (2× 20 ml). The organic layer was washed with brine solution (2× 20 ml), dried over anhydrous sodium sulfate and concentrated in vacuum. The residue was then subjected to column chromatography (silica gel, 100–200 mesh) with hexane-ethylacetate (8:2) to obtain the cycloadduct. Single crystals were obtained by recrystallization from methanol.