
Acta Cryst. (2008). E64, o488 [ doi:10.1107/S1600536807068705 ]
The thiazolidine ring and the pyrrolidine ring in the title compound, C25H26N2O2S, both adopt an envelope conformation. The seven-membered ring has a twist-chair conformation. The crystal packing is stabilized by intermolecular N-H
O hydrogen bonds.
A mixture of isatin (0.147 g, 1 mmol), thiaproline, (0.135 g, 1 mmol) and benzylidenecycloheptanone (1 mmol) in methanol (20 ml) was refluxed until the disappearance of the starting materials. The reaction mixture was then concentrated in vacuo and extracted with water (50 ml) and dichloromethane (50 ml). The organic layer was washed with brine solution, dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography with hexane-ethylacetate (8:2) mixture to get title compound. The pure compound was recrystallized from ethanol.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).
| C25H26N2O2S | Z = 2 |
| Mr = 418.54 | F000 = 444 |
| Triclinic, P1 | Dx = 1.337 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 8.9846 (10) Å | Cell parameters from 2358 reflections |
| b = 10.3564 (11) Å | θ = 1.7–25.0º |
| c = 12.8124 (14) Å | µ = 0.18 mm−1 |
| α = 80.147 (2)º | T = 293 (2) K |
| β = 71.012 (2)º | Block, colorless |
| γ = 67.497 (2)º | 0.26 × 0.25 × 0.23 mm |
| V = 1040.0 (2) Å3 |
| Bruker SMART CCD area-detector diffractometer | 3880 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.023 |
| Monochromator: graphite | θmax = 28.0º |
| T = 293(2) K | θmin = 1.7º |
| ω scans | h = −11→11 |
| Absorption correction: none | k = −13→13 |
| 11582 measured reflections | l = −16→16 |
| 4697 independent reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
| wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0833P)2 + 0.2981P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max < 0.001 |
| 4697 reflections | Δρmax = 0.36 e Å−3 |
| 271 parameters | Δρmin = −0.20 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C25H26N2O2S | γ = 67.497 (2)º |
| Mr = 418.54 | V = 1040.0 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.9846 (10) Å | Mo Kα |
| b = 10.3564 (11) Å | µ = 0.18 mm−1 |
| c = 12.8124 (14) Å | T = 293 (2) K |
| α = 80.147 (2)º | 0.26 × 0.25 × 0.23 mm |
| β = 71.012 (2)º |
| Bruker SMART CCD area-detector diffractometer | 4697 independent reflections |
| Absorption correction: none | 3880 reflections with I > 2σ(I) |
| 11582 measured reflections | Rint = 0.023 |
| R[F2 > 2σ(F2)] = 0.062 | 271 parameters |
| wR(F2) = 0.157 | H-atom parameters constrained |
| S = 1.08 | Δρmax = 0.36 e Å−3 |
| 4697 reflections | Δρmin = −0.20 e Å−3 |
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. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.2327 (2) | 0.71980 (19) | 0.35784 (14) | 0.0267 (4) | |
| C2 | 0.1643 (2) | 0.84561 (18) | 0.27522 (14) | 0.0245 (4) | |
| C3 | 0.2629 (2) | 0.93969 (19) | 0.27834 (14) | 0.0275 (4) | |
| H3 | 0.3807 | 0.8916 | 0.2386 | 0.033* | |
| C4 | 0.2543 (2) | 0.9308 (2) | 0.39991 (15) | 0.0309 (4) | |
| H4 | 0.1503 | 1.0022 | 0.4386 | 0.037* | |
| C5 | 0.4043 (3) | 0.9465 (3) | 0.4219 (2) | 0.0486 (6) | |
| H5A | 0.3675 | 0.9961 | 0.4887 | 0.058* | |
| H5B | 0.4568 | 0.9989 | 0.3607 | 0.058* | |
| C6 | 0.3716 (3) | 0.7143 (3) | 0.4993 (2) | 0.0477 (6) | |
| H6A | 0.4063 | 0.6146 | 0.4918 | 0.057* | |
| H6B | 0.3256 | 0.7325 | 0.5773 | 0.057* | |
| C7 | 0.1116 (2) | 0.63856 (19) | 0.41978 (14) | 0.0283 (4) | |
| C8 | 0.3423 (3) | 0.4830 (2) | 0.31052 (16) | 0.0340 (4) | |
| C9 | 0.4440 (3) | 0.3632 (2) | 0.25409 (19) | 0.0474 (6) | |
| H9 | 0.4118 | 0.2855 | 0.2648 | 0.057* | |
| C10 | 0.5958 (3) | 0.3639 (3) | 0.1810 (2) | 0.0552 (7) | |
| H10 | 0.6665 | 0.2857 | 0.1404 | 0.066* | |
| C11 | 0.6440 (3) | 0.4783 (3) | 0.1674 (2) | 0.0521 (6) | |
| H11 | 0.7482 | 0.4750 | 0.1193 | 0.063* | |
| C12 | 0.5404 (3) | 0.5984 (2) | 0.22390 (18) | 0.0410 (5) | |
| H12 | 0.5741 | 0.6752 | 0.2141 | 0.049* | |
| C13 | 0.3852 (2) | 0.6016 (2) | 0.29553 (15) | 0.0311 (4) | |
| C14 | 0.2143 (3) | 0.79473 (19) | 0.15917 (15) | 0.0312 (4) | |
| C15 | 0.1212 (3) | 0.7116 (2) | 0.13959 (18) | 0.0435 (5) | |
| H15A | 0.0694 | 0.6711 | 0.2093 | 0.052* | |
| H15B | 0.1990 | 0.6360 | 0.0920 | 0.052* | |
| C16 | −0.0142 (4) | 0.8082 (3) | 0.0852 (2) | 0.0584 (7) | |
| H16A | 0.0370 | 0.8584 | 0.0216 | 0.070* | |
| H16B | −0.0576 | 0.7514 | 0.0588 | 0.070* | |
| C17 | −0.1593 (3) | 0.9132 (3) | 0.1619 (2) | 0.0600 (7) | |
| H17A | −0.2234 | 0.8631 | 0.2172 | 0.072* | |
| H17B | −0.2326 | 0.9763 | 0.1193 | 0.072* | |
| C18 | −0.1110 (3) | 1.0007 (2) | 0.22123 (19) | 0.0433 (5) | |
| H18A | −0.2113 | 1.0777 | 0.2538 | 0.052* | |
| H18B | −0.0339 | 1.0406 | 0.1669 | 0.052* | |
| C19 | −0.0288 (2) | 0.9197 (2) | 0.31231 (15) | 0.0307 (4) | |
| H19A | −0.0793 | 0.8497 | 0.3474 | 0.037* | |
| H19B | −0.0561 | 0.9844 | 0.3679 | 0.037* | |
| C20 | 0.2132 (2) | 1.0876 (2) | 0.22729 (15) | 0.0300 (4) | |
| C21 | 0.3124 (3) | 1.1172 (2) | 0.12397 (17) | 0.0393 (5) | |
| H21 | 0.4070 | 1.0459 | 0.0876 | 0.047* | |
| C22 | 0.2726 (3) | 1.2504 (3) | 0.07487 (19) | 0.0503 (6) | |
| H22 | 0.3406 | 1.2681 | 0.0060 | 0.060* | |
| C23 | 0.1336 (4) | 1.3570 (2) | 0.1268 (2) | 0.0512 (6) | |
| H23 | 0.1051 | 1.4461 | 0.0924 | 0.061* | |
| C24 | 0.0365 (3) | 1.3313 (2) | 0.2302 (2) | 0.0477 (6) | |
| H24 | −0.0565 | 1.4039 | 0.2665 | 0.057* | |
| C25 | 0.0765 (3) | 1.1980 (2) | 0.28063 (18) | 0.0385 (5) | |
| H25 | 0.0110 | 1.1822 | 0.3511 | 0.046* | |
| N1 | 0.2471 (2) | 0.79135 (17) | 0.44146 (12) | 0.0312 (4) | |
| N2 | 0.1822 (2) | 0.50686 (17) | 0.38528 (14) | 0.0365 (4) | |
| H2 | 0.1347 | 0.4451 | 0.4066 | 0.044* | |
| O1 | −0.02147 (18) | 0.68469 (15) | 0.49036 (11) | 0.0377 (3) | |
| O2 | 0.3167 (2) | 0.82744 (17) | 0.08308 (11) | 0.0449 (4) | |
| S1 | 0.55069 (8) | 0.77332 (8) | 0.43717 (6) | 0.0609 (2) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0286 (9) | 0.0307 (9) | 0.0235 (8) | −0.0144 (8) | −0.0074 (7) | 0.0014 (7) |
| C2 | 0.0295 (9) | 0.0258 (9) | 0.0194 (8) | −0.0125 (7) | −0.0066 (7) | 0.0012 (7) |
| C3 | 0.0301 (9) | 0.0301 (9) | 0.0234 (9) | −0.0143 (8) | −0.0045 (7) | −0.0014 (7) |
| C4 | 0.0358 (10) | 0.0354 (10) | 0.0264 (9) | −0.0176 (8) | −0.0091 (8) | −0.0014 (8) |
| C5 | 0.0577 (15) | 0.0605 (15) | 0.0485 (13) | −0.0368 (12) | −0.0255 (11) | 0.0027 (11) |
| C6 | 0.0591 (15) | 0.0524 (14) | 0.0437 (12) | −0.0251 (12) | −0.0296 (11) | 0.0099 (10) |
| C7 | 0.0345 (10) | 0.0316 (10) | 0.0220 (8) | −0.0166 (8) | −0.0096 (7) | 0.0051 (7) |
| C8 | 0.0395 (11) | 0.0309 (10) | 0.0289 (9) | −0.0104 (9) | −0.0115 (8) | 0.0039 (8) |
| C9 | 0.0591 (15) | 0.0308 (11) | 0.0446 (12) | −0.0088 (10) | −0.0154 (11) | 0.0015 (9) |
| C10 | 0.0559 (15) | 0.0376 (12) | 0.0446 (13) | 0.0071 (11) | −0.0077 (11) | −0.0015 (10) |
| C11 | 0.0362 (12) | 0.0530 (15) | 0.0435 (13) | −0.0005 (11) | −0.0028 (10) | 0.0044 (11) |
| C12 | 0.0337 (11) | 0.0433 (12) | 0.0383 (11) | −0.0108 (9) | −0.0075 (9) | 0.0052 (9) |
| C13 | 0.0316 (10) | 0.0327 (10) | 0.0259 (9) | −0.0092 (8) | −0.0100 (8) | 0.0043 (7) |
| C14 | 0.0404 (11) | 0.0272 (9) | 0.0255 (9) | −0.0110 (8) | −0.0103 (8) | 0.0001 (7) |
| C15 | 0.0661 (15) | 0.0409 (12) | 0.0357 (11) | −0.0268 (11) | −0.0212 (10) | −0.0010 (9) |
| C16 | 0.0824 (19) | 0.0688 (17) | 0.0485 (14) | −0.0382 (15) | −0.0401 (14) | 0.0050 (12) |
| C17 | 0.0601 (16) | 0.0745 (18) | 0.0625 (16) | −0.0296 (14) | −0.0409 (14) | 0.0135 (14) |
| C18 | 0.0408 (12) | 0.0444 (12) | 0.0435 (12) | −0.0107 (10) | −0.0202 (10) | 0.0068 (10) |
| C19 | 0.0298 (10) | 0.0352 (10) | 0.0259 (9) | −0.0123 (8) | −0.0075 (8) | 0.0028 (8) |
| C20 | 0.0372 (10) | 0.0313 (10) | 0.0273 (9) | −0.0189 (8) | −0.0090 (8) | 0.0001 (7) |
| C21 | 0.0471 (12) | 0.0397 (11) | 0.0316 (10) | −0.0215 (10) | −0.0057 (9) | 0.0000 (9) |
| C22 | 0.0710 (17) | 0.0501 (14) | 0.0367 (12) | −0.0360 (13) | −0.0131 (11) | 0.0110 (10) |
| C23 | 0.0764 (17) | 0.0352 (12) | 0.0554 (14) | −0.0290 (12) | −0.0331 (13) | 0.0147 (10) |
| C24 | 0.0562 (14) | 0.0318 (11) | 0.0581 (14) | −0.0125 (10) | −0.0222 (12) | −0.0057 (10) |
| C25 | 0.0442 (12) | 0.0363 (11) | 0.0350 (10) | −0.0169 (9) | −0.0070 (9) | −0.0037 (9) |
| N1 | 0.0371 (9) | 0.0375 (9) | 0.0259 (8) | −0.0184 (7) | −0.0141 (7) | 0.0032 (7) |
| N2 | 0.0430 (10) | 0.0299 (8) | 0.0372 (9) | −0.0191 (7) | −0.0074 (8) | 0.0041 (7) |
| O1 | 0.0382 (8) | 0.0393 (8) | 0.0332 (7) | −0.0206 (6) | −0.0002 (6) | 0.0013 (6) |
| O2 | 0.0558 (10) | 0.0530 (9) | 0.0247 (7) | −0.0257 (8) | 0.0002 (7) | −0.0059 (6) |
| S1 | 0.0454 (4) | 0.0753 (5) | 0.0743 (5) | −0.0243 (3) | −0.0318 (3) | 0.0007 (4) |
| C1—N1 | 1.466 (2) | C12—C13 | 1.389 (3) |
| C1—C13 | 1.534 (3) | C12—H12 | 0.9300 |
| C1—C7 | 1.560 (2) | C14—O2 | 1.206 (2) |
| C1—C2 | 1.592 (2) | C14—C15 | 1.505 (3) |
| C2—C14 | 1.531 (2) | C15—C16 | 1.532 (3) |
| C2—C19 | 1.547 (3) | C15—H15A | 0.9700 |
| C2—C3 | 1.560 (2) | C15—H15B | 0.9700 |
| C3—C20 | 1.516 (3) | C16—C17 | 1.514 (4) |
| C3—C4 | 1.523 (2) | C16—H16A | 0.9700 |
| C3—H3 | 0.9800 | C16—H16B | 0.9700 |
| C4—N1 | 1.469 (2) | C17—C18 | 1.530 (3) |
| C4—C5 | 1.535 (3) | C17—H17A | 0.9700 |
| C4—H4 | 0.9800 | C17—H17B | 0.9700 |
| C5—S1 | 1.796 (3) | C18—C19 | 1.537 (3) |
| C5—H5A | 0.9700 | C18—H18A | 0.9700 |
| C5—H5B | 0.9700 | C18—H18B | 0.9700 |
| C6—N1 | 1.445 (3) | C19—H19A | 0.9700 |
| C6—S1 | 1.830 (2) | C19—H19B | 0.9700 |
| C6—H6A | 0.9700 | C20—C25 | 1.389 (3) |
| C6—H6B | 0.9700 | C20—C21 | 1.394 (3) |
| C7—O1 | 1.217 (2) | C21—C22 | 1.378 (3) |
| C7—N2 | 1.349 (2) | C21—H21 | 0.9300 |
| C8—C9 | 1.381 (3) | C22—C23 | 1.370 (4) |
| C8—C13 | 1.388 (3) | C22—H22 | 0.9300 |
| C8—N2 | 1.400 (3) | C23—C24 | 1.375 (4) |
| C9—C10 | 1.382 (3) | C23—H23 | 0.9300 |
| C9—H9 | 0.9300 | C24—C25 | 1.385 (3) |
| C10—C11 | 1.377 (4) | C24—H24 | 0.9300 |
| C10—H10 | 0.9300 | C25—H25 | 0.9300 |
| C11—C12 | 1.386 (3) | N2—H2 | 0.8600 |
| C11—H11 | 0.9300 | ||
| N1—C1—C13 | 120.41 (15) | O2—C14—C2 | 121.75 (17) |
| N1—C1—C7 | 106.89 (14) | C15—C14—C2 | 118.00 (17) |
| C13—C1—C7 | 100.64 (14) | C14—C15—C16 | 109.25 (18) |
| N1—C1—C2 | 102.68 (14) | C14—C15—H15A | 109.8 |
| C13—C1—C2 | 111.37 (14) | C16—C15—H15A | 109.8 |
| C7—C1—C2 | 115.44 (14) | C14—C15—H15B | 109.8 |
| C14—C2—C19 | 108.15 (15) | C16—C15—H15B | 109.8 |
| C14—C2—C3 | 111.12 (14) | H15A—C15—H15B | 108.3 |
| C19—C2—C3 | 113.41 (15) | C17—C16—C15 | 113.6 (2) |
| C14—C2—C1 | 110.81 (14) | C17—C16—H16A | 108.8 |
| C19—C2—C1 | 113.62 (14) | C15—C16—H16A | 108.8 |
| C3—C2—C1 | 99.60 (13) | C17—C16—H16B | 108.8 |
| C20—C3—C4 | 114.20 (15) | C15—C16—H16B | 108.8 |
| C20—C3—C2 | 118.60 (15) | H16A—C16—H16B | 107.7 |
| C4—C3—C2 | 103.40 (14) | C16—C17—C18 | 115.7 (2) |
| C20—C3—H3 | 106.6 | C16—C17—H17A | 108.4 |
| C4—C3—H3 | 106.6 | C18—C17—H17A | 108.4 |
| C2—C3—H3 | 106.6 | C16—C17—H17B | 108.4 |
| N1—C4—C3 | 104.86 (14) | C18—C17—H17B | 108.4 |
| N1—C4—C5 | 109.38 (17) | H17A—C17—H17B | 107.4 |
| C3—C4—C5 | 114.85 (16) | C17—C18—C19 | 114.69 (19) |
| N1—C4—H4 | 109.2 | C17—C18—H18A | 108.6 |
| C3—C4—H4 | 109.2 | C19—C18—H18A | 108.6 |
| C5—C4—H4 | 109.2 | C17—C18—H18B | 108.6 |
| C4—C5—S1 | 107.24 (15) | C19—C18—H18B | 108.6 |
| C4—C5—H5A | 110.3 | H18A—C18—H18B | 107.6 |
| S1—C5—H5A | 110.3 | C18—C19—C2 | 116.35 (16) |
| C4—C5—H5B | 110.3 | C18—C19—H19A | 108.2 |
| S1—C5—H5B | 110.3 | C2—C19—H19A | 108.2 |
| H5A—C5—H5B | 108.5 | C18—C19—H19B | 108.2 |
| N1—C6—S1 | 107.08 (15) | C2—C19—H19B | 108.2 |
| N1—C6—H6A | 110.3 | H19A—C19—H19B | 107.4 |
| S1—C6—H6A | 110.3 | C25—C20—C21 | 117.67 (18) |
| N1—C6—H6B | 110.3 | C25—C20—C3 | 123.12 (17) |
| S1—C6—H6B | 110.3 | C21—C20—C3 | 119.15 (18) |
| H6A—C6—H6B | 108.6 | C22—C21—C20 | 121.1 (2) |
| O1—C7—N2 | 125.70 (17) | C22—C21—H21 | 119.5 |
| O1—C7—C1 | 125.71 (17) | C20—C21—H21 | 119.5 |
| N2—C7—C1 | 108.54 (16) | C23—C22—C21 | 120.4 (2) |
| C9—C8—C13 | 123.1 (2) | C23—C22—H22 | 119.8 |
| C9—C8—N2 | 126.65 (19) | C21—C22—H22 | 119.8 |
| C13—C8—N2 | 110.23 (17) | C22—C23—C24 | 119.5 (2) |
| C8—C9—C10 | 117.0 (2) | C22—C23—H23 | 120.2 |
| C8—C9—H9 | 121.5 | C24—C23—H23 | 120.2 |
| C10—C9—H9 | 121.5 | C23—C24—C25 | 120.4 (2) |
| C11—C10—C9 | 121.1 (2) | C23—C24—H24 | 119.8 |
| C11—C10—H10 | 119.5 | C25—C24—H24 | 119.8 |
| C9—C10—H10 | 119.5 | C24—C25—C20 | 120.8 (2) |
| C10—C11—C12 | 121.4 (2) | C24—C25—H25 | 119.6 |
| C10—C11—H11 | 119.3 | C20—C25—H25 | 119.6 |
| C12—C11—H11 | 119.3 | C6—N1—C1 | 117.96 (17) |
| C11—C12—C13 | 118.6 (2) | C6—N1—C4 | 112.11 (16) |
| C11—C12—H12 | 120.7 | C1—N1—C4 | 111.66 (14) |
| C13—C12—H12 | 120.7 | C7—N2—C8 | 111.73 (16) |
| C8—C13—C12 | 118.80 (19) | C7—N2—H2 | 124.1 |
| C8—C13—C1 | 108.37 (16) | C8—N2—H2 | 124.1 |
| C12—C13—C1 | 132.51 (18) | C5—S1—C6 | 88.36 (11) |
| O2—C14—C15 | 120.06 (18) | ||
| N1—C1—C2—C14 | 154.06 (15) | C3—C2—C14—O2 | −0.4 (3) |
| C13—C1—C2—C14 | 23.9 (2) | C1—C2—C14—O2 | −110.2 (2) |
| C7—C1—C2—C14 | −90.04 (18) | C19—C2—C14—C15 | −50.3 (2) |
| N1—C1—C2—C19 | −83.94 (17) | C3—C2—C14—C15 | −175.42 (17) |
| C13—C1—C2—C19 | 145.89 (16) | C1—C2—C14—C15 | 74.8 (2) |
| C7—C1—C2—C19 | 32.0 (2) | O2—C14—C15—C16 | −75.9 (3) |
| N1—C1—C2—C3 | 36.98 (16) | C2—C14—C15—C16 | 99.2 (2) |
| C13—C1—C2—C3 | −93.19 (16) | C14—C15—C16—C17 | −70.3 (3) |
| C7—C1—C2—C3 | 152.88 (15) | C15—C16—C17—C18 | 52.0 (3) |
| C14—C2—C3—C20 | 74.5 (2) | C16—C17—C18—C19 | −71.4 (3) |
| C19—C2—C3—C20 | −47.6 (2) | C17—C18—C19—C2 | 87.6 (2) |
| C1—C2—C3—C20 | −168.64 (15) | C14—C2—C19—C18 | −34.2 (2) |
| C14—C2—C3—C4 | −157.92 (15) | C3—C2—C19—C18 | 89.6 (2) |
| C19—C2—C3—C4 | 80.01 (17) | C1—C2—C19—C18 | −157.62 (16) |
| C1—C2—C3—C4 | −41.06 (17) | C4—C3—C20—C25 | −42.5 (3) |
| C20—C3—C4—N1 | 160.57 (15) | C2—C3—C20—C25 | 79.8 (2) |
| C2—C3—C4—N1 | 30.29 (18) | C4—C3—C20—C21 | 134.67 (19) |
| C20—C3—C4—C5 | −79.4 (2) | C2—C3—C20—C21 | −103.0 (2) |
| C2—C3—C4—C5 | 150.37 (17) | C25—C20—C21—C22 | −2.2 (3) |
| N1—C4—C5—S1 | 22.4 (2) | C3—C20—C21—C22 | −179.53 (19) |
| C3—C4—C5—S1 | −95.20 (18) | C20—C21—C22—C23 | −0.2 (4) |
| N1—C1—C7—O1 | 45.1 (2) | C21—C22—C23—C24 | 2.1 (4) |
| C13—C1—C7—O1 | 171.63 (18) | C22—C23—C24—C25 | −1.5 (4) |
| C2—C1—C7—O1 | −68.4 (2) | C23—C24—C25—C20 | −1.0 (3) |
| N1—C1—C7—N2 | −132.43 (16) | C21—C20—C25—C24 | 2.8 (3) |
| C13—C1—C7—N2 | −5.90 (18) | C3—C20—C25—C24 | −179.97 (19) |
| C2—C1—C7—N2 | 114.09 (17) | S1—C6—N1—C1 | 101.84 (17) |
| C13—C8—C9—C10 | 0.9 (3) | S1—C6—N1—C4 | −30.0 (2) |
| N2—C8—C9—C10 | 177.8 (2) | C13—C1—N1—C6 | −27.7 (2) |
| C8—C9—C10—C11 | 1.4 (4) | C7—C1—N1—C6 | 86.0 (2) |
| C9—C10—C11—C12 | −1.9 (4) | C2—C1—N1—C6 | −152.11 (16) |
| C10—C11—C12—C13 | 0.1 (4) | C13—C1—N1—C4 | 104.30 (18) |
| C9—C8—C13—C12 | −2.7 (3) | C7—C1—N1—C4 | −142.00 (16) |
| N2—C8—C13—C12 | 179.99 (17) | C2—C1—N1—C4 | −20.10 (19) |
| C9—C8—C13—C1 | 171.59 (19) | C3—C4—N1—C6 | 128.85 (18) |
| N2—C8—C13—C1 | −5.7 (2) | C5—C4—N1—C6 | 5.2 (2) |
| C11—C12—C13—C8 | 2.1 (3) | C3—C4—N1—C1 | −6.0 (2) |
| C11—C12—C13—C1 | −170.5 (2) | C5—C4—N1—C1 | −129.71 (17) |
| N1—C1—C13—C8 | 123.82 (18) | O1—C7—N2—C8 | −174.57 (18) |
| C7—C1—C13—C8 | 6.88 (19) | C1—C7—N2—C8 | 3.0 (2) |
| C2—C1—C13—C8 | −116.00 (16) | C9—C8—N2—C7 | −175.5 (2) |
| N1—C1—C13—C12 | −63.0 (3) | C13—C8—N2—C7 | 1.8 (2) |
| C7—C1—C13—C12 | −179.9 (2) | C4—C5—S1—C6 | −33.23 (16) |
| C2—C1—C13—C12 | 57.2 (3) | N1—C6—S1—C5 | 36.70 (17) |
| C19—C2—C14—O2 | 124.6 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1i | 0.86 | 2.04 | 2.859 (2) | 160 |
| Symmetry codes: (i) −x, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1i | 0.86 | 2.04 | 2.859 (2) | 160 |
| Symmetry codes: (i) −x, −y+1, −z+1. |
DG thanks the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship. Financial support from the University Grants Commission (UGC–SAP) and the Department of Science & Technology (DST–FIST), Government of India, is acknowledged by DV for providing facilities to the department.
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It has been reported that pyrrolidine derivatives reduce Coxsackievirus B3 replication through inhibition of the Ubiquitin-Proteasome pathway (Si et al., 2005). They are found to have antimicrobial and antifungal activity against various pathogens except Bacillus subtilis (Amal Raj et al., 2003). As the derivatives of pyrrolidine and oxindole are of pharmacological importance, we have undertaken the X-ray crystal structure determination of the title compound.
The bond lengths and bond angles of the title compound are comparable with a similar structure (Kumar et al., 2006). The sum of the bond angles around N1 atom [341.8 (5)°] indicates sp3 hybridization. The dihedral angle between the phenyl ring and the six membered in the oxindole moiety is 40.5 (1)°.
The thiazolidine ring adopts an envelope conformation with S1 atom deviating by 0.764 (1) Å. The pyrrolidine ring (N1/C1—C4) adopts an envelope conformation with C2 atom deviating by -0.655 (2) Å. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for the pyrrolidine ring, five membered ring (N2/C7/C1/C13/C8) in the oxindole moiety and the thiazolidine ring are q2 = 0.424 (2), 0.068 (2), 0.443 (2) Å, φ = 80.4 (3), 264.7 (18), 355.5 (3)° and Δs(C2) = 7.7 (2), Δ2(N2) = 0.9 (3), Δs(S1) = 5.9 (2).
The crystal packing is stabilized by intermolecular N—H···O hydrogen bonds generating a centrosymmetric dimeric ring motif [R22(8)].