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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o515.
Published online 2008 January 25. doi:  10.1107/S1600536808002134
PMCID: PMC2960171

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

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 [triangle]). For asymmetry parameters, see: Nardelli (1983 [triangle]). For general background, see: Amal Raj et al. (2003 [triangle]); Tsuru et al. (1988 [triangle]). For a related structure, see: Kavitha et al. (2006 [triangle]).

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Object name is e-64-0o515-scheme1.jpg

Experimental

Crystal data

  • C21H24N2O3S2
  • M r = 416.54
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o515-efi1.jpg
  • 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
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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, [var phi] = 187.3 (3)° and Δs(N1) = 6.5 (2)° for ring A, q2 = 0.372 (2) Å, [var phi] = 137.0 (3)° and Δs(C6) = 4.2 (2)° for ring B, and q2 = 0.378 (2) Å, [var phi] = 69.8 (3)° and Δs(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.

Refinement

H atoms were included in calculated positions and treated in the subsequent refinement as riding atoms, with C—H = 0.93–0.98 Å and Uiso(H) = 1.2–1.5(methyl) Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
Fig. 2.
The crystal packing of the title compound viewed down the b axis.

Crystal data

C21H24N2O3S2F000 = 880
Mr = 416.54Dx = 1.368 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2394 reflections
a = 14.5533 (8) Åθ = 2.4–28.0º
b = 8.3319 (5) ŵ = 0.29 mm1
c = 16.8828 (9) ÅT = 293 (2) K
β = 98.923 (1)ºBlock, pale yellow
V = 2022.4 (2) Å30.24 × 0.23 × 0.21 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer3991 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Monochromator: graphiteθmax = 28.0º
T = 293(2) Kθmin = 2.4º
ω scansh = −18→18
Absorption correction: nonek = −10→11
22482 measured reflectionsl = −21→22
4769 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.137  w = 1/[σ2(Fo2) + (0.082P)2 + 0.473P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4769 reflectionsΔρmax = 0.46 e Å3
254 parametersΔρmin = −0.16 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.65354 (11)0.0421 (2)0.27798 (12)0.0543 (4)
H1A0.62060.00860.22620.065*
H1B0.61160.03710.31730.065*
C20.74011 (12)−0.0593 (2)0.30329 (11)0.0518 (4)
H20.7317−0.16810.28130.062*
C30.81895 (10)0.0293 (2)0.26945 (9)0.0439 (3)
H30.8425−0.03560.22850.053*
C40.77552 (11)0.1850 (2)0.23356 (11)0.0526 (4)
H4A0.81800.27470.24530.063*
H4B0.75760.17600.17600.063*
C50.77266 (13)−0.0635 (3)0.39390 (11)0.0626 (5)
H5A0.74810.02700.42010.075*
H5B0.7534−0.16220.41710.075*
C60.87749 (12)−0.0543 (3)0.40161 (10)0.0569 (4)
H60.9046−0.01320.45450.068*
C70.92284 (15)−0.2141 (3)0.38422 (15)0.0727 (6)
H7A0.8825−0.27420.34360.087*
H7B0.9354−0.27880.43250.087*
C80.98632 (10)0.04673 (19)0.32061 (9)0.0436 (3)
H80.98400.05900.26260.052*
C91.05361 (11)0.16890 (19)0.36222 (9)0.0436 (3)
C101.14935 (12)0.1485 (2)0.36544 (12)0.0550 (4)
H101.17130.05770.34230.066*
C111.21182 (12)0.2592 (2)0.40186 (11)0.0564 (4)
H111.27520.24260.40320.068*
C121.18109 (11)0.3950 (2)0.43660 (9)0.0479 (4)
C131.08652 (11)0.4217 (2)0.43145 (10)0.0494 (4)
H131.06490.51490.45260.059*
C141.02415 (11)0.3086 (2)0.39456 (10)0.0478 (4)
H140.96070.32740.39150.057*
C151.22176 (17)0.6174 (3)0.52376 (16)0.0805 (6)
H15A1.18520.69670.49180.121*
H15B1.27630.66690.55290.121*
H15C1.18570.57070.56080.121*
C160.56879 (11)0.3179 (2)0.15034 (11)0.0500 (4)
C170.48978 (12)0.2243 (2)0.13751 (13)0.0618 (5)
H170.46220.18850.18040.074*
C180.45196 (16)0.1844 (3)0.05922 (17)0.0806 (7)
H180.39910.12030.04970.097*
C190.4920 (2)0.2388 (4)−0.00370 (16)0.0903 (8)
H190.46640.2110−0.05580.108*
C200.56928 (18)0.3335 (4)0.00945 (16)0.0913 (8)
H200.59560.3713−0.03370.110*
C210.60859 (14)0.3736 (3)0.08689 (14)0.0717 (6)
H210.66150.43770.09590.086*
N10.69349 (9)0.20342 (17)0.27399 (8)0.0463 (3)
N20.89254 (8)0.05860 (16)0.33850 (7)0.0425 (3)
O11.24842 (9)0.49627 (18)0.47326 (9)0.0655 (4)
O20.55465 (11)0.3473 (2)0.30071 (10)0.0803 (5)
O30.68031 (11)0.49379 (17)0.24897 (11)0.0845 (5)
S11.02851 (3)−0.16174 (6)0.34950 (3)0.06126 (16)
S20.62353 (3)0.35418 (5)0.24924 (3)0.05671 (16)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0391 (8)0.0524 (9)0.0690 (11)−0.0053 (7)0.0012 (7)0.0057 (8)
C20.0474 (9)0.0442 (8)0.0619 (10)−0.0017 (7)0.0025 (7)0.0016 (7)
C30.0408 (7)0.0513 (9)0.0379 (7)0.0052 (6)0.0013 (6)−0.0012 (6)
C40.0375 (8)0.0647 (11)0.0543 (9)0.0039 (7)0.0033 (7)0.0166 (8)
C50.0539 (10)0.0767 (13)0.0591 (10)0.0051 (9)0.0148 (8)0.0172 (9)
C60.0501 (9)0.0787 (13)0.0418 (8)0.0110 (9)0.0065 (7)0.0119 (8)
C70.0654 (12)0.0688 (13)0.0853 (14)0.0174 (10)0.0158 (10)0.0367 (11)
C80.0414 (7)0.0472 (8)0.0412 (7)0.0091 (6)0.0033 (6)0.0006 (6)
C90.0405 (8)0.0486 (8)0.0402 (7)0.0083 (6)0.0018 (6)0.0033 (6)
C100.0434 (8)0.0551 (10)0.0650 (10)0.0143 (7)0.0035 (7)−0.0071 (8)
C110.0369 (8)0.0617 (11)0.0681 (11)0.0100 (7)0.0006 (7)−0.0002 (9)
C120.0454 (8)0.0520 (9)0.0441 (8)0.0009 (7)0.0005 (6)0.0052 (7)
C130.0495 (9)0.0479 (9)0.0507 (9)0.0068 (7)0.0080 (7)−0.0013 (7)
C140.0380 (7)0.0537 (9)0.0513 (9)0.0088 (7)0.0052 (6)−0.0007 (7)
C150.0727 (13)0.0751 (14)0.0901 (16)−0.0104 (12)0.0017 (12)−0.0244 (12)
C160.0384 (8)0.0460 (8)0.0629 (10)0.0071 (6)−0.0007 (7)0.0056 (7)
C170.0448 (9)0.0581 (11)0.0795 (13)−0.0016 (8)−0.0002 (8)0.0085 (9)
C180.0584 (12)0.0700 (13)0.1027 (18)−0.0003 (10)−0.0211 (12)−0.0081 (13)
C190.0831 (17)0.108 (2)0.0723 (14)0.0324 (15)−0.0127 (12)−0.0067 (14)
C200.0679 (14)0.135 (2)0.0702 (14)0.0243 (15)0.0080 (11)0.0286 (14)
C210.0458 (9)0.0839 (14)0.0830 (14)0.0029 (9)0.0022 (9)0.0269 (12)
N10.0369 (6)0.0462 (7)0.0539 (7)0.0004 (5)0.0009 (5)−0.0001 (6)
N20.0384 (6)0.0499 (7)0.0376 (6)0.0061 (5)0.0012 (5)−0.0003 (5)
O10.0506 (7)0.0672 (8)0.0754 (9)−0.0045 (6)−0.0007 (6)−0.0105 (7)
O20.0724 (9)0.0955 (12)0.0742 (9)0.0299 (8)0.0151 (7)−0.0118 (8)
O30.0785 (10)0.0448 (7)0.1191 (13)−0.0049 (7)−0.0199 (9)−0.0081 (8)
S10.0558 (3)0.0487 (3)0.0802 (3)0.01351 (19)0.0134 (2)−0.0004 (2)
S20.0506 (3)0.0477 (3)0.0683 (3)0.00750 (18)−0.0018 (2)−0.00786 (19)

Geometric parameters (Å, °)

C1—N11.470 (2)C10—C111.372 (3)
C1—C21.522 (2)C10—H100.93
C1—H1A0.97C11—C121.381 (3)
C1—H1B0.97C11—H110.93
C2—C51.530 (3)C12—O11.367 (2)
C2—C31.546 (2)C12—C131.384 (2)
C2—H20.98C13—C141.387 (2)
C3—N21.4760 (18)C13—H130.93
C3—C41.527 (2)C14—H140.93
C3—H30.98C15—O11.413 (3)
C4—N11.472 (2)C15—H15A0.96
C4—H4A0.97C15—H15B0.96
C4—H4B0.97C15—H15C0.96
C5—C61.513 (2)C16—C211.375 (3)
C5—H5A0.97C16—C171.378 (2)
C5—H5B0.97C16—S21.7611 (18)
C6—N21.463 (2)C17—C181.391 (3)
C6—C71.534 (3)C17—H170.93
C6—H60.98C18—C191.366 (4)
C7—S11.783 (2)C18—H180.93
C7—H7A0.97C19—C201.364 (4)
C7—H7B0.97C19—H190.93
C8—N21.4461 (19)C20—C211.384 (4)
C8—C91.508 (2)C20—H200.93
C8—S11.8812 (16)C21—H210.93
C8—H80.98N1—S21.630 (1)
C9—C141.382 (2)O2—S21.426 (2)
C9—C101.396 (2)O3—S21.427 (2)
N1—C1—C2101.78 (13)C11—C10—H10119.2
N1—C1—H1A111.4C9—C10—H10119.2
C2—C1—H1A111.4C10—C11—C12120.36 (15)
N1—C1—H1B111.4C10—C11—H11119.8
C2—C1—H1B111.4C12—C11—H11119.8
H1A—C1—H1B109.3O1—C12—C11116.22 (15)
C1—C2—C5114.08 (16)O1—C12—C13124.43 (16)
C1—C2—C3105.12 (13)C11—C12—C13119.34 (16)
C5—C2—C3104.36 (13)C12—C13—C14119.61 (16)
C1—C2—H2111.0C12—C13—H13120.2
C5—C2—H2111.0C14—C13—H13120.2
C3—C2—H2111.0C9—C14—C13121.87 (15)
N2—C3—C4112.20 (14)C9—C14—H14119.1
N2—C3—C2106.04 (12)C13—C14—H14119.1
C4—C3—C2105.49 (12)O1—C15—H15A109.5
N2—C3—H3111.0O1—C15—H15B109.5
C4—C3—H3111.0H15A—C15—H15B109.5
C2—C3—H3111.0O1—C15—H15C109.5
N1—C4—C3102.71 (13)H15A—C15—H15C109.5
N1—C4—H4A111.2H15B—C15—H15C109.5
C3—C4—H4A111.2C21—C16—C17120.69 (19)
N1—C4—H4B111.2C21—C16—S2119.82 (15)
C3—C4—H4B111.2C17—C16—S2119.33 (15)
H4A—C4—H4B109.1C16—C17—C18118.8 (2)
C6—C5—C2103.68 (14)C16—C17—H17120.6
C6—C5—H5A111.0C18—C17—H17120.6
C2—C5—H5A111.0C19—C18—C17120.4 (2)
C6—C5—H5B111.0C19—C18—H18119.8
C2—C5—H5B111.0C17—C18—H18119.8
H5A—C5—H5B109.0C18—C19—C20120.4 (2)
N2—C6—C5103.46 (13)C18—C19—H19119.8
N2—C6—C7107.54 (14)C20—C19—H19119.8
C5—C6—C7113.43 (19)C19—C20—C21120.2 (2)
N2—C6—H6110.7C19—C20—H20119.9
C5—C6—H6110.7C21—C20—H20119.9
C7—C6—H6110.7C16—C21—C20119.5 (2)
C6—C7—S1105.61 (15)C16—C21—H21120.3
C6—C7—H7A110.6C20—C21—H21120.3
S1—C7—H7A110.6C1—N1—C4106.32 (14)
C6—C7—H7B110.6C1—N1—S2118.72 (10)
S1—C7—H7B110.6C4—N1—S2118.72 (11)
H7A—C7—H7B108.8C8—N2—C6111.15 (12)
N2—C8—C9114.97 (13)C8—N2—C3114.61 (12)
N2—C8—S1106.84 (11)C6—N2—C3107.25 (13)
C9—C8—S1109.88 (10)C12—O1—C15117.99 (15)
N2—C8—H8108.3C7—S1—C892.74 (8)
C9—C8—H8108.3O3—S2—O2119.8 (1)
S1—C8—H8108.3O3—S2—N1106.9 (1)
C14—C9—C10117.13 (16)O2—S2—N1106.4 (1)
C14—C9—C8122.25 (14)O3—S2—C16108.3 (1)
C10—C9—C8120.52 (14)O2—S2—C16108.3 (1)
C11—C10—C9121.58 (16)N1—S2—C16106.5 (1)
N1—C1—C2—C584.89 (18)C19—C20—C21—C16−0.4 (4)
N1—C1—C2—C3−28.83 (17)C2—C1—N1—C443.59 (17)
C1—C2—C3—N2124.51 (14)C2—C1—N1—S2−179.41 (12)
C5—C2—C3—N24.15 (18)C3—C4—N1—C1−40.24 (16)
C1—C2—C3—C45.32 (18)C3—C4—N1—S2−177.24 (11)
C5—C2—C3—C4−115.04 (15)C9—C8—N2—C6−96.95 (16)
N2—C3—C4—N1−94.75 (15)S1—C8—N2—C625.25 (15)
C2—C3—C4—N120.26 (17)C9—C8—N2—C3141.25 (14)
C1—C2—C5—C6−140.00 (16)S1—C8—N2—C3−96.54 (13)
C3—C2—C5—C6−25.83 (19)C5—C6—N2—C8−162.77 (15)
C2—C5—C6—N238.5 (2)C7—C6—N2—C8−42.48 (19)
C2—C5—C6—C7−77.72 (19)C5—C6—N2—C3−36.79 (18)
N2—C6—C7—S139.16 (19)C7—C6—N2—C383.51 (17)
C5—C6—C7—S1152.93 (13)C4—C3—N2—C8−101.22 (15)
N2—C8—C9—C14−18.7 (2)C2—C3—N2—C8144.10 (13)
S1—C8—C9—C14−139.26 (14)C4—C3—N2—C6134.88 (14)
N2—C8—C9—C10164.94 (15)C2—C3—N2—C620.21 (17)
S1—C8—C9—C1044.39 (19)C11—C12—O1—C15−166.82 (19)
C14—C9—C10—C112.5 (3)C13—C12—O1—C1514.2 (3)
C8—C9—C10—C11178.99 (17)C6—C7—S1—C8−21.16 (15)
C9—C10—C11—C120.0 (3)N2—C8—S1—C7−1.24 (13)
C10—C11—C12—O1178.36 (17)C9—C8—S1—C7124.11 (13)
C10—C11—C12—C13−2.6 (3)C1—N1—S2—O3−179.18 (14)
O1—C12—C13—C14−178.35 (16)C4—N1—S2—O3−47.46 (16)
C11—C12—C13—C142.7 (3)C1—N1—S2—O251.72 (16)
C10—C9—C14—C13−2.4 (3)C4—N1—S2—O2−176.55 (13)
C8—C9—C14—C13−178.82 (15)C1—N1—S2—C16−63.61 (15)
C12—C13—C14—C9−0.2 (3)C4—N1—S2—C1668.11 (14)
C21—C16—C17—C181.3 (3)C21—C16—S2—O324.79 (18)
S2—C16—C17—C18−174.25 (15)C17—C16—S2—O3−159.64 (15)
C16—C17—C18—C19−0.7 (3)C21—C16—S2—O2156.12 (16)
C17—C18—C19—C20−0.3 (4)C17—C16—S2—O2−28.32 (18)
C18—C19—C20—C210.9 (4)C21—C16—S2—N1−89.80 (17)
C17—C16—C21—C20−0.7 (3)C17—C16—S2—N185.77 (16)
S2—C16—C21—C20174.78 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C18—H18···O1i0.932.563.437 (3)158
C3—H3···Cg1ii0.982.763.729 (2)172

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2542).

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