In the title compound, C
21H
24N
2O
3S
2, 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.
Supporting information
CCDC reference: 677647
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.137
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.89
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT793_ALERT_2_G Check the Absolute Configuration of C2 ..... S
PLAT793_ALERT_2_G Check the Absolute Configuration of C3 ..... S
PLAT793_ALERT_2_G Check the Absolute Configuration of C6 ..... S
PLAT793_ALERT_2_G Check the Absolute Configuration of C8 ..... R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
6 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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.
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).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008) and PARST (Nardelli, 1995).
3-(4-Methoxyphenyl)-6-(phenylsulfonyl)perhydro-1,3-
thiazolo[3',4':1,2]pyrrolo[4,5-
c]pyrrole
top
Crystal data top
C21H24N2O3S2 | F(000) = 880 |
Mr = 416.54 | Dx = 1.368 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2394 reflections |
a = 14.5533 (8) Å | θ = 2.4–28.0° |
b = 8.3319 (5) Å | µ = 0.29 mm−1 |
c = 16.8828 (9) Å | T = 293 K |
β = 98.923 (1)° | Block, pale yellow |
V = 2022.4 (2) Å3 | 0.24 × 0.23 × 0.21 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3991 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 28.0°, θmin = 2.4° |
ω scans | h = −18→18 |
22482 measured reflections | k = −10→11 |
4769 independent reflections | l = −21→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.082P)2 + 0.473P] where P = (Fo2 + 2Fc2)/3 |
4769 reflections | (Δ/σ)max = 0.001 |
254 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Crystal data top
C21H24N2O3S2 | V = 2022.4 (2) Å3 |
Mr = 416.54 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.5533 (8) Å | µ = 0.29 mm−1 |
b = 8.3319 (5) Å | T = 293 K |
c = 16.8828 (9) Å | 0.24 × 0.23 × 0.21 mm |
β = 98.923 (1)° | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3991 reflections with I > 2σ(I) |
22482 measured reflections | Rint = 0.020 |
4769 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.46 e Å−3 |
4769 reflections | Δρmin = −0.16 e Å−3 |
254 parameters | |
Special details top
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) top | x | y | z | Uiso*/Ueq | |
C1 | 0.65354 (11) | 0.0421 (2) | 0.27798 (12) | 0.0543 (4) | |
H1A | 0.6206 | 0.0086 | 0.2262 | 0.065* | |
H1B | 0.6116 | 0.0371 | 0.3173 | 0.065* | |
C2 | 0.74011 (12) | −0.0593 (2) | 0.30329 (11) | 0.0518 (4) | |
H2 | 0.7317 | −0.1681 | 0.2813 | 0.062* | |
C3 | 0.81895 (10) | 0.0293 (2) | 0.26945 (9) | 0.0439 (3) | |
H3 | 0.8425 | −0.0356 | 0.2285 | 0.053* | |
C4 | 0.77552 (11) | 0.1850 (2) | 0.23356 (11) | 0.0526 (4) | |
H4A | 0.8180 | 0.2747 | 0.2453 | 0.063* | |
H4B | 0.7576 | 0.1760 | 0.1760 | 0.063* | |
C5 | 0.77266 (13) | −0.0635 (3) | 0.39390 (11) | 0.0626 (5) | |
H5A | 0.7481 | 0.0270 | 0.4201 | 0.075* | |
H5B | 0.7534 | −0.1622 | 0.4171 | 0.075* | |
C6 | 0.87749 (12) | −0.0543 (3) | 0.40161 (10) | 0.0569 (4) | |
H6 | 0.9046 | −0.0132 | 0.4545 | 0.068* | |
C7 | 0.92284 (15) | −0.2141 (3) | 0.38422 (15) | 0.0727 (6) | |
H7A | 0.8825 | −0.2742 | 0.3436 | 0.087* | |
H7B | 0.9354 | −0.2788 | 0.4325 | 0.087* | |
C8 | 0.98632 (10) | 0.04673 (19) | 0.32061 (9) | 0.0436 (3) | |
H8 | 0.9840 | 0.0590 | 0.2626 | 0.052* | |
C9 | 1.05361 (11) | 0.16890 (19) | 0.36222 (9) | 0.0436 (3) | |
C10 | 1.14935 (12) | 0.1485 (2) | 0.36544 (12) | 0.0550 (4) | |
H10 | 1.1713 | 0.0577 | 0.3423 | 0.066* | |
C11 | 1.21182 (12) | 0.2592 (2) | 0.40186 (11) | 0.0564 (4) | |
H11 | 1.2752 | 0.2426 | 0.4032 | 0.068* | |
C12 | 1.18109 (11) | 0.3950 (2) | 0.43660 (9) | 0.0479 (4) | |
C13 | 1.08652 (11) | 0.4217 (2) | 0.43145 (10) | 0.0494 (4) | |
H13 | 1.0649 | 0.5149 | 0.4526 | 0.059* | |
C14 | 1.02415 (11) | 0.3086 (2) | 0.39456 (10) | 0.0478 (4) | |
H14 | 0.9607 | 0.3274 | 0.3915 | 0.057* | |
C15 | 1.22176 (17) | 0.6174 (3) | 0.52376 (16) | 0.0805 (6) | |
H15A | 1.1852 | 0.6967 | 0.4918 | 0.121* | |
H15B | 1.2763 | 0.6669 | 0.5529 | 0.121* | |
H15C | 1.1857 | 0.5707 | 0.5608 | 0.121* | |
C16 | 0.56879 (11) | 0.3179 (2) | 0.15034 (11) | 0.0500 (4) | |
C17 | 0.48978 (12) | 0.2243 (2) | 0.13751 (13) | 0.0618 (5) | |
H17 | 0.4622 | 0.1885 | 0.1804 | 0.074* | |
C18 | 0.45196 (16) | 0.1844 (3) | 0.05922 (17) | 0.0806 (7) | |
H18 | 0.3991 | 0.1203 | 0.0497 | 0.097* | |
C19 | 0.4920 (2) | 0.2388 (4) | −0.00370 (16) | 0.0903 (8) | |
H19 | 0.4664 | 0.2110 | −0.0558 | 0.108* | |
C20 | 0.56928 (18) | 0.3335 (4) | 0.00945 (16) | 0.0913 (8) | |
H20 | 0.5956 | 0.3713 | −0.0337 | 0.110* | |
C21 | 0.60859 (14) | 0.3736 (3) | 0.08689 (14) | 0.0717 (6) | |
H21 | 0.6615 | 0.4377 | 0.0959 | 0.086* | |
N1 | 0.69349 (9) | 0.20342 (17) | 0.27399 (8) | 0.0463 (3) | |
N2 | 0.89254 (8) | 0.05860 (16) | 0.33850 (7) | 0.0425 (3) | |
O1 | 1.24842 (9) | 0.49627 (18) | 0.47326 (9) | 0.0655 (4) | |
O2 | 0.55465 (11) | 0.3473 (2) | 0.30071 (10) | 0.0803 (5) | |
O3 | 0.68031 (11) | 0.49379 (17) | 0.24897 (11) | 0.0845 (5) | |
S1 | 1.02851 (3) | −0.16174 (6) | 0.34950 (3) | 0.06126 (16) | |
S2 | 0.62353 (3) | 0.35418 (5) | 0.24924 (3) | 0.05671 (16) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0391 (8) | 0.0524 (9) | 0.0690 (11) | −0.0053 (7) | 0.0012 (7) | 0.0057 (8) |
C2 | 0.0474 (9) | 0.0442 (8) | 0.0619 (10) | −0.0017 (7) | 0.0025 (7) | 0.0016 (7) |
C3 | 0.0408 (7) | 0.0513 (9) | 0.0379 (7) | 0.0052 (6) | 0.0013 (6) | −0.0012 (6) |
C4 | 0.0375 (8) | 0.0647 (11) | 0.0543 (9) | 0.0039 (7) | 0.0033 (7) | 0.0166 (8) |
C5 | 0.0539 (10) | 0.0767 (13) | 0.0591 (10) | 0.0051 (9) | 0.0148 (8) | 0.0172 (9) |
C6 | 0.0501 (9) | 0.0787 (13) | 0.0418 (8) | 0.0110 (9) | 0.0065 (7) | 0.0119 (8) |
C7 | 0.0654 (12) | 0.0688 (13) | 0.0853 (14) | 0.0174 (10) | 0.0158 (10) | 0.0367 (11) |
C8 | 0.0414 (7) | 0.0472 (8) | 0.0412 (7) | 0.0091 (6) | 0.0033 (6) | 0.0006 (6) |
C9 | 0.0405 (8) | 0.0486 (8) | 0.0402 (7) | 0.0083 (6) | 0.0018 (6) | 0.0033 (6) |
C10 | 0.0434 (8) | 0.0551 (10) | 0.0650 (10) | 0.0143 (7) | 0.0035 (7) | −0.0071 (8) |
C11 | 0.0369 (8) | 0.0617 (11) | 0.0681 (11) | 0.0100 (7) | 0.0006 (7) | −0.0002 (9) |
C12 | 0.0454 (8) | 0.0520 (9) | 0.0441 (8) | 0.0009 (7) | 0.0005 (6) | 0.0052 (7) |
C13 | 0.0495 (9) | 0.0479 (9) | 0.0507 (9) | 0.0068 (7) | 0.0080 (7) | −0.0013 (7) |
C14 | 0.0380 (7) | 0.0537 (9) | 0.0513 (9) | 0.0088 (7) | 0.0052 (6) | −0.0007 (7) |
C15 | 0.0727 (13) | 0.0751 (14) | 0.0901 (16) | −0.0104 (12) | 0.0017 (12) | −0.0244 (12) |
C16 | 0.0384 (8) | 0.0460 (8) | 0.0629 (10) | 0.0071 (6) | −0.0007 (7) | 0.0056 (7) |
C17 | 0.0448 (9) | 0.0581 (11) | 0.0795 (13) | −0.0016 (8) | −0.0002 (8) | 0.0085 (9) |
C18 | 0.0584 (12) | 0.0700 (13) | 0.1027 (18) | −0.0003 (10) | −0.0211 (12) | −0.0081 (13) |
C19 | 0.0831 (17) | 0.108 (2) | 0.0723 (14) | 0.0324 (15) | −0.0127 (12) | −0.0067 (14) |
C20 | 0.0679 (14) | 0.135 (2) | 0.0702 (14) | 0.0243 (15) | 0.0080 (11) | 0.0286 (14) |
C21 | 0.0458 (9) | 0.0839 (14) | 0.0830 (14) | 0.0029 (9) | 0.0022 (9) | 0.0269 (12) |
N1 | 0.0369 (6) | 0.0462 (7) | 0.0539 (7) | 0.0004 (5) | 0.0009 (5) | −0.0001 (6) |
N2 | 0.0384 (6) | 0.0499 (7) | 0.0376 (6) | 0.0061 (5) | 0.0012 (5) | −0.0003 (5) |
O1 | 0.0506 (7) | 0.0672 (8) | 0.0754 (9) | −0.0045 (6) | −0.0007 (6) | −0.0105 (7) |
O2 | 0.0724 (9) | 0.0955 (12) | 0.0742 (9) | 0.0299 (8) | 0.0151 (7) | −0.0118 (8) |
O3 | 0.0785 (10) | 0.0448 (7) | 0.1191 (13) | −0.0049 (7) | −0.0199 (9) | −0.0081 (8) |
S1 | 0.0558 (3) | 0.0487 (3) | 0.0802 (3) | 0.01351 (19) | 0.0134 (2) | −0.0004 (2) |
S2 | 0.0506 (3) | 0.0477 (3) | 0.0683 (3) | 0.00750 (18) | −0.0018 (2) | −0.00786 (19) |
Geometric parameters (Å, º) top
C1—N1 | 1.470 (2) | C10—C11 | 1.372 (3) |
C1—C2 | 1.522 (2) | C10—H10 | 0.93 |
C1—H1A | 0.97 | C11—C12 | 1.381 (3) |
C1—H1B | 0.97 | C11—H11 | 0.93 |
C2—C5 | 1.530 (3) | C12—O1 | 1.367 (2) |
C2—C3 | 1.546 (2) | C12—C13 | 1.384 (2) |
C2—H2 | 0.98 | C13—C14 | 1.387 (2) |
C3—N2 | 1.4760 (18) | C13—H13 | 0.93 |
C3—C4 | 1.527 (2) | C14—H14 | 0.93 |
C3—H3 | 0.98 | C15—O1 | 1.413 (3) |
C4—N1 | 1.472 (2) | C15—H15A | 0.96 |
C4—H4A | 0.97 | C15—H15B | 0.96 |
C4—H4B | 0.97 | C15—H15C | 0.96 |
C5—C6 | 1.513 (2) | C16—C21 | 1.375 (3) |
C5—H5A | 0.97 | C16—C17 | 1.378 (2) |
C5—H5B | 0.97 | C16—S2 | 1.7611 (18) |
C6—N2 | 1.463 (2) | C17—C18 | 1.391 (3) |
C6—C7 | 1.534 (3) | C17—H17 | 0.93 |
C6—H6 | 0.98 | C18—C19 | 1.366 (4) |
C7—S1 | 1.783 (2) | C18—H18 | 0.93 |
C7—H7A | 0.97 | C19—C20 | 1.364 (4) |
C7—H7B | 0.97 | C19—H19 | 0.93 |
C8—N2 | 1.4461 (19) | C20—C21 | 1.384 (4) |
C8—C9 | 1.508 (2) | C20—H20 | 0.93 |
C8—S1 | 1.8812 (16) | C21—H21 | 0.93 |
C8—H8 | 0.98 | N1—S2 | 1.630 (1) |
C9—C14 | 1.382 (2) | O2—S2 | 1.426 (2) |
C9—C10 | 1.396 (2) | O3—S2 | 1.427 (2) |
| | | |
N1—C1—C2 | 101.78 (13) | C11—C10—H10 | 119.2 |
N1—C1—H1A | 111.4 | C9—C10—H10 | 119.2 |
C2—C1—H1A | 111.4 | C10—C11—C12 | 120.36 (15) |
N1—C1—H1B | 111.4 | C10—C11—H11 | 119.8 |
C2—C1—H1B | 111.4 | C12—C11—H11 | 119.8 |
H1A—C1—H1B | 109.3 | O1—C12—C11 | 116.22 (15) |
C1—C2—C5 | 114.08 (16) | O1—C12—C13 | 124.43 (16) |
C1—C2—C3 | 105.12 (13) | C11—C12—C13 | 119.34 (16) |
C5—C2—C3 | 104.36 (13) | C12—C13—C14 | 119.61 (16) |
C1—C2—H2 | 111.0 | C12—C13—H13 | 120.2 |
C5—C2—H2 | 111.0 | C14—C13—H13 | 120.2 |
C3—C2—H2 | 111.0 | C9—C14—C13 | 121.87 (15) |
N2—C3—C4 | 112.20 (14) | C9—C14—H14 | 119.1 |
N2—C3—C2 | 106.04 (12) | C13—C14—H14 | 119.1 |
C4—C3—C2 | 105.49 (12) | O1—C15—H15A | 109.5 |
N2—C3—H3 | 111.0 | O1—C15—H15B | 109.5 |
C4—C3—H3 | 111.0 | H15A—C15—H15B | 109.5 |
C2—C3—H3 | 111.0 | O1—C15—H15C | 109.5 |
N1—C4—C3 | 102.71 (13) | H15A—C15—H15C | 109.5 |
N1—C4—H4A | 111.2 | H15B—C15—H15C | 109.5 |
C3—C4—H4A | 111.2 | C21—C16—C17 | 120.69 (19) |
N1—C4—H4B | 111.2 | C21—C16—S2 | 119.82 (15) |
C3—C4—H4B | 111.2 | C17—C16—S2 | 119.33 (15) |
H4A—C4—H4B | 109.1 | C16—C17—C18 | 118.8 (2) |
C6—C5—C2 | 103.68 (14) | C16—C17—H17 | 120.6 |
C6—C5—H5A | 111.0 | C18—C17—H17 | 120.6 |
C2—C5—H5A | 111.0 | C19—C18—C17 | 120.4 (2) |
C6—C5—H5B | 111.0 | C19—C18—H18 | 119.8 |
C2—C5—H5B | 111.0 | C17—C18—H18 | 119.8 |
H5A—C5—H5B | 109.0 | C18—C19—C20 | 120.4 (2) |
N2—C6—C5 | 103.46 (13) | C18—C19—H19 | 119.8 |
N2—C6—C7 | 107.54 (14) | C20—C19—H19 | 119.8 |
C5—C6—C7 | 113.43 (19) | C19—C20—C21 | 120.2 (2) |
N2—C6—H6 | 110.7 | C19—C20—H20 | 119.9 |
C5—C6—H6 | 110.7 | C21—C20—H20 | 119.9 |
C7—C6—H6 | 110.7 | C16—C21—C20 | 119.5 (2) |
C6—C7—S1 | 105.61 (15) | C16—C21—H21 | 120.3 |
C6—C7—H7A | 110.6 | C20—C21—H21 | 120.3 |
S1—C7—H7A | 110.6 | C1—N1—C4 | 106.32 (14) |
C6—C7—H7B | 110.6 | C1—N1—S2 | 118.72 (10) |
S1—C7—H7B | 110.6 | C4—N1—S2 | 118.72 (11) |
H7A—C7—H7B | 108.8 | C8—N2—C6 | 111.15 (12) |
N2—C8—C9 | 114.97 (13) | C8—N2—C3 | 114.61 (12) |
N2—C8—S1 | 106.84 (11) | C6—N2—C3 | 107.25 (13) |
C9—C8—S1 | 109.88 (10) | C12—O1—C15 | 117.99 (15) |
N2—C8—H8 | 108.3 | C7—S1—C8 | 92.74 (8) |
C9—C8—H8 | 108.3 | O3—S2—O2 | 119.8 (1) |
S1—C8—H8 | 108.3 | O3—S2—N1 | 106.9 (1) |
C14—C9—C10 | 117.13 (16) | O2—S2—N1 | 106.4 (1) |
C14—C9—C8 | 122.25 (14) | O3—S2—C16 | 108.3 (1) |
C10—C9—C8 | 120.52 (14) | O2—S2—C16 | 108.3 (1) |
C11—C10—C9 | 121.58 (16) | N1—S2—C16 | 106.5 (1) |
| | | |
N1—C1—C2—C5 | 84.89 (18) | C19—C20—C21—C16 | −0.4 (4) |
N1—C1—C2—C3 | −28.83 (17) | C2—C1—N1—C4 | 43.59 (17) |
C1—C2—C3—N2 | 124.51 (14) | C2—C1—N1—S2 | −179.41 (12) |
C5—C2—C3—N2 | 4.15 (18) | C3—C4—N1—C1 | −40.24 (16) |
C1—C2—C3—C4 | 5.32 (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—C6 | 25.25 (15) |
C2—C3—C4—N1 | 20.26 (17) | C9—C8—N2—C3 | 141.25 (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—N2 | 38.5 (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—S1 | 39.16 (19) | C7—C6—N2—C3 | 83.51 (17) |
C5—C6—C7—S1 | 152.93 (13) | C4—C3—N2—C8 | −101.22 (15) |
N2—C8—C9—C14 | −18.7 (2) | C2—C3—N2—C8 | 144.10 (13) |
S1—C8—C9—C14 | −139.26 (14) | C4—C3—N2—C6 | 134.88 (14) |
N2—C8—C9—C10 | 164.94 (15) | C2—C3—N2—C6 | 20.21 (17) |
S1—C8—C9—C10 | 44.39 (19) | C11—C12—O1—C15 | −166.82 (19) |
C14—C9—C10—C11 | 2.5 (3) | C13—C12—O1—C15 | 14.2 (3) |
C8—C9—C10—C11 | 178.99 (17) | C6—C7—S1—C8 | −21.16 (15) |
C9—C10—C11—C12 | 0.0 (3) | N2—C8—S1—C7 | −1.24 (13) |
C10—C11—C12—O1 | 178.36 (17) | C9—C8—S1—C7 | 124.11 (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—C14 | 2.7 (3) | C1—N1—S2—O2 | 51.72 (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—C16 | 68.11 (14) |
C21—C16—C17—C18 | 1.3 (3) | C21—C16—S2—O3 | 24.79 (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—O2 | 156.12 (16) |
C17—C18—C19—C20 | −0.3 (4) | C17—C16—S2—O2 | −28.32 (18) |
C18—C19—C20—C21 | 0.9 (4) | C21—C16—S2—N1 | −89.80 (17) |
C17—C16—C21—C20 | −0.7 (3) | C17—C16—S2—N1 | 85.77 (16) |
S2—C16—C21—C20 | 174.78 (18) | | |
Hydrogen-bond geometry (Å, º) top
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 |
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+2, y−1/2, −z+1/2. |
Experimental details
Crystal data |
Chemical formula | C21H24N2O3S2 |
Mr | 416.54 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.5533 (8), 8.3319 (5), 16.8828 (9) |
β (°) | 98.923 (1) |
V (Å3) | 2022.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.24 × 0.23 × 0.21 |
|
Data collection |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22482, 4769, 3991 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.661 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.137, 1.00 |
No. of reflections | 4769 |
No. of parameters | 254 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.16 |
Hydrogen-bond geometry (Å, º) top
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 |
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+2, y−1/2, −z+1/2. |
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 Δs(N1) = 6.5 (2)° for ring A, q2 = 0.372 (2) Å, ϕ = 137.0 (3)° and Δs(C6) = 4.2 (2)° for ring B, and q2 = 0.378 (2) Å, ϕ = 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.