Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008298/cv6184sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008298/cv6184Isup2.hkl |
CCDC reference: 214624
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.039
- wR factor = 0.104
- Data-to-parameter ratio = 17.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C21 H23 I1 N2 O2 S1 Atom count from _chemical_formula_moiety:C21 H23 I2 N2 O2 S1
A 100 ml round-bottomed flask equipped with a condenser and an air moisture-impermeable seal, was charged with sarcosine (4 mmol), paraformaldehyde (8 mmol) and 5-benzylidene-3-benzyl-thiazolidine-2,4-dione (2 mmol). The reaction mixture was refluxed in dry toluene (60 ml) until the starting 5-benzylidene-3-benzylthiazolidine-2,4-dione was consumed. After evaporation of the solvent, the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 2:1), the product got from column chromatography then stirred with methyl iodide in acetone at room temperature for 1 h, the title compound, (I), was achieved by filtration. M.p. 535–536 K; IR (KBr): 2920 (CH2CH3), 1753, 1676 (C═O) cm−1; 1H NMR (CD3CN, p.p.m.): 3.52 (6H, s), 4.04–4.11 (1H, m), 4.34–4.42 (2H, m), 4.50–4.59 (2H, m), 4.68–4.79 (2H, m), 6.94–7.44 (10H, m); 20 mg of (I) was dissolved in 15 ml CH3CN, the solution was kept at room temperature for 20 d by natural evaporation to give colorless single crystals of (I), suitable for X-ray analysis.
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. A view of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. |
C21H23IN2O2S+·I− | F(000) = 992 |
Mr = 494.37 | Dx = 1.540 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.791 (7) Å | Cell parameters from 953 reflections |
b = 7.606 (3) Å | θ = 2.9–25.6° |
c = 13.484 (5) Å | µ = 1.62 mm−1 |
β = 90.685 (5)° | T = 293 K |
V = 2132.1 (12) Å3 | Plate, colorless |
Z = 4 | 0.30 × 0.14 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 4347 independent reflections |
Radiation source: fine-focus sealed tube | 2790 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −25→25 |
Tmin = 0.675, Tmax = 0.851 | k = −9→5 |
11395 measured reflections | l = −16→16 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.039 | (Δ/σ)max = 0.001 |
wR(F2) = 0.104 | Δρmax = 0.74 e Å−3 |
S = 1.02 | Δρmin = −0.47 e Å−3 |
4347 reflections | Extinction correction: SHELXL97 |
247 parameters | Extinction coefficient: 0.0077 (4) |
0 restraints |
C21H23IN2O2S+·I− | V = 2132.1 (12) Å3 |
Mr = 494.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.791 (7) Å | µ = 1.62 mm−1 |
b = 7.606 (3) Å | T = 293 K |
c = 13.484 (5) Å | 0.30 × 0.14 × 0.10 mm |
β = 90.685 (5)° |
Bruker SMART CCD area-detector diffractometer | 4347 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 2790 reflections with I > 2σ(I) |
Tmin = 0.675, Tmax = 0.851 | Rint = 0.040 |
11395 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.74 e Å−3 |
4347 reflections | Δρmin = −0.47 e Å−3 |
247 parameters |
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 | ||
I1 | 0.077786 (15) | 0.76597 (4) | 0.30466 (2) | 0.05754 (15) | |
S1 | 0.19206 (6) | 0.67442 (15) | 0.02632 (8) | 0.0498 (3) | |
N1 | 0.23735 (17) | 0.6319 (5) | 0.2053 (2) | 0.0429 (8) | |
N2 | 0.09920 (15) | 0.2477 (4) | 0.0182 (2) | 0.0367 (7) | |
O1 | 0.19851 (17) | 0.3631 (4) | 0.2508 (2) | 0.0604 (9) | |
O2 | 0.25474 (18) | 0.9042 (4) | 0.1376 (3) | 0.0794 (12) | |
C1 | 0.2041 (2) | 0.4794 (5) | 0.1898 (3) | 0.0387 (10) | |
C2 | 0.2329 (2) | 0.7566 (6) | 0.1314 (4) | 0.0514 (11) | |
C3 | 0.17776 (19) | 0.4612 (5) | 0.0846 (3) | 0.0336 (9) | |
C4 | 0.1053 (2) | 0.4141 (6) | 0.0797 (4) | 0.0507 (12) | |
H4A | 0.0890 | 0.3947 | 0.1459 | 0.061* | |
H4B | 0.0810 | 0.5090 | 0.0491 | 0.061* | |
C5 | 0.16060 (19) | 0.2397 (5) | −0.0403 (3) | 0.0438 (10) | |
H5A | 0.1584 | 0.3169 | −0.0975 | 0.053* | |
H5B | 0.1692 | 0.1208 | −0.0626 | 0.053* | |
C6 | 0.21191 (19) | 0.3012 (5) | 0.0332 (3) | 0.0384 (10) | |
H6 | 0.2163 | 0.2088 | 0.0834 | 0.046* | |
C7 | 0.2652 (2) | 0.6746 (8) | 0.3041 (4) | 0.0660 (15) | |
H7A | 0.2440 | 0.6031 | 0.3536 | 0.079* | |
H7B | 0.2560 | 0.7968 | 0.3190 | 0.079* | |
C8 | 0.3375 (3) | 0.6451 (7) | 0.3125 (4) | 0.0639 (14) | |
C9 | 0.3788 (3) | 0.6811 (11) | 0.2369 (6) | 0.108 (3) | |
H9 | 0.3621 | 0.7154 | 0.1756 | 0.130* | |
C10 | 0.4447 (4) | 0.6680 (13) | 0.2493 (8) | 0.127 (3) | |
H10 | 0.4721 | 0.6961 | 0.1977 | 0.152* | |
C11 | 0.4687 (4) | 0.6138 (13) | 0.3373 (10) | 0.145 (5) | |
H11 | 0.5128 | 0.6001 | 0.3459 | 0.174* | |
C12 | 0.4283 (5) | 0.5788 (13) | 0.4141 (9) | 0.147 (4) | |
H12 | 0.4454 | 0.5431 | 0.4749 | 0.176* | |
C13 | 0.3616 (3) | 0.5959 (8) | 0.4025 (6) | 0.096 (2) | |
H13 | 0.3343 | 0.5741 | 0.4553 | 0.115* | |
C14 | 0.0422 (2) | 0.2554 (6) | −0.0515 (4) | 0.0577 (12) | |
H14A | 0.0416 | 0.1523 | −0.0925 | 0.086* | |
H14B | 0.0454 | 0.3581 | −0.0925 | 0.086* | |
H14C | 0.0034 | 0.2607 | −0.0139 | 0.086* | |
C15 | 0.0924 (2) | 0.0890 (6) | 0.0835 (4) | 0.0597 (13) | |
H15A | 0.0923 | −0.0153 | 0.0434 | 0.089* | |
H15B | 0.0528 | 0.0965 | 0.1191 | 0.089* | |
H15C | 0.1278 | 0.0845 | 0.1298 | 0.089* | |
C16 | 0.2790 (2) | 0.3374 (5) | −0.0058 (4) | 0.0466 (11) | |
C17 | 0.2904 (3) | 0.3710 (6) | −0.1053 (4) | 0.0622 (14) | |
H17 | 0.2563 | 0.3695 | −0.1507 | 0.075* | |
C18 | 0.3523 (3) | 0.4068 (7) | −0.1378 (5) | 0.0820 (19) | |
H18 | 0.3597 | 0.4277 | −0.2047 | 0.098* | |
C19 | 0.4027 (3) | 0.4112 (9) | −0.0707 (6) | 0.094 (2) | |
H19 | 0.4439 | 0.4374 | −0.0921 | 0.112* | |
C20 | 0.3922 (3) | 0.3773 (9) | 0.0271 (6) | 0.093 (2) | |
H20 | 0.4264 | 0.3804 | 0.0722 | 0.112* | |
C21 | 0.3302 (2) | 0.3378 (8) | 0.0599 (5) | 0.0720 (15) | |
H21 | 0.3235 | 0.3118 | 0.1264 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0515 (2) | 0.0679 (2) | 0.0534 (2) | 0.00499 (17) | 0.00931 (14) | 0.00278 (17) |
S1 | 0.0705 (8) | 0.0409 (6) | 0.0382 (6) | 0.0115 (6) | 0.0036 (6) | 0.0102 (5) |
N1 | 0.043 (2) | 0.049 (2) | 0.0362 (19) | 0.0022 (17) | −0.0004 (16) | −0.0101 (17) |
N2 | 0.0386 (17) | 0.0338 (18) | 0.0379 (17) | −0.0002 (15) | 0.0067 (14) | −0.0014 (16) |
O1 | 0.083 (2) | 0.062 (2) | 0.0358 (17) | 0.0117 (19) | 0.0116 (16) | 0.0174 (16) |
O2 | 0.084 (3) | 0.0392 (19) | 0.115 (3) | −0.0095 (18) | 0.003 (2) | −0.010 (2) |
C1 | 0.042 (2) | 0.043 (2) | 0.032 (2) | 0.0121 (19) | 0.0072 (19) | 0.0017 (19) |
C2 | 0.050 (3) | 0.040 (3) | 0.065 (3) | 0.007 (2) | 0.010 (2) | −0.009 (2) |
C3 | 0.040 (2) | 0.031 (2) | 0.030 (2) | 0.0045 (17) | 0.0053 (17) | 0.0007 (16) |
C4 | 0.045 (3) | 0.050 (3) | 0.057 (3) | 0.003 (2) | 0.007 (2) | −0.020 (2) |
C5 | 0.046 (2) | 0.042 (2) | 0.043 (2) | −0.003 (2) | 0.0163 (19) | −0.010 (2) |
C6 | 0.043 (2) | 0.032 (2) | 0.041 (2) | 0.0036 (17) | 0.0103 (19) | −0.0039 (17) |
C7 | 0.057 (3) | 0.095 (4) | 0.046 (3) | 0.003 (3) | −0.007 (2) | −0.026 (3) |
C8 | 0.056 (3) | 0.064 (3) | 0.071 (4) | 0.003 (3) | −0.016 (3) | −0.024 (3) |
C9 | 0.059 (4) | 0.175 (7) | 0.091 (5) | 0.024 (4) | −0.001 (4) | −0.036 (5) |
C10 | 0.059 (5) | 0.171 (8) | 0.150 (8) | 0.021 (5) | 0.000 (5) | −0.050 (7) |
C11 | 0.058 (5) | 0.123 (8) | 0.252 (15) | 0.008 (5) | −0.035 (7) | −0.033 (9) |
C12 | 0.106 (7) | 0.123 (7) | 0.210 (12) | 0.008 (6) | −0.093 (8) | 0.029 (7) |
C13 | 0.095 (5) | 0.079 (4) | 0.113 (6) | −0.008 (4) | −0.036 (5) | 0.014 (4) |
C14 | 0.044 (3) | 0.070 (3) | 0.058 (3) | −0.001 (3) | −0.006 (2) | 0.001 (3) |
C15 | 0.053 (3) | 0.051 (3) | 0.076 (3) | 0.007 (2) | 0.016 (3) | 0.023 (3) |
C16 | 0.042 (3) | 0.038 (2) | 0.061 (3) | 0.0032 (19) | 0.013 (2) | −0.007 (2) |
C17 | 0.064 (3) | 0.059 (3) | 0.064 (3) | −0.011 (3) | 0.023 (3) | −0.013 (3) |
C18 | 0.082 (4) | 0.075 (4) | 0.090 (4) | −0.019 (3) | 0.043 (4) | −0.018 (3) |
C19 | 0.061 (4) | 0.085 (5) | 0.137 (7) | −0.007 (3) | 0.040 (4) | −0.019 (5) |
C20 | 0.047 (3) | 0.106 (5) | 0.126 (6) | 0.012 (3) | −0.003 (4) | −0.017 (5) |
C21 | 0.046 (3) | 0.084 (4) | 0.087 (4) | 0.016 (3) | 0.005 (3) | −0.007 (3) |
S1—C2 | 1.759 (5) | C9—C10 | 1.382 (10) |
S1—C3 | 1.828 (4) | C9—H9 | 0.9300 |
N1—C1 | 1.366 (5) | C10—C11 | 1.345 (13) |
N1—C2 | 1.377 (6) | C10—H10 | 0.9300 |
N1—C7 | 1.482 (5) | C11—C12 | 1.366 (13) |
N2—C15 | 1.501 (5) | C11—H11 | 0.9300 |
N2—C14 | 1.504 (6) | C12—C13 | 1.401 (10) |
N2—C5 | 1.510 (5) | C12—H12 | 0.9300 |
N2—C4 | 1.518 (5) | C13—H13 | 0.9300 |
O1—C1 | 1.215 (5) | C14—H14A | 0.9600 |
O2—C2 | 1.214 (5) | C14—H14B | 0.9600 |
C1—C3 | 1.520 (5) | C14—H14C | 0.9600 |
C3—C4 | 1.549 (6) | C15—H15A | 0.9600 |
C3—C6 | 1.574 (5) | C15—H15B | 0.9600 |
C4—H4A | 0.9700 | C15—H15C | 0.9600 |
C4—H4B | 0.9700 | C16—C21 | 1.376 (7) |
C5—C6 | 1.521 (6) | C16—C17 | 1.389 (7) |
C5—H5A | 0.9700 | C17—C18 | 1.392 (7) |
C5—H5B | 0.9700 | C17—H17 | 0.9300 |
C6—C16 | 1.522 (6) | C18—C19 | 1.375 (9) |
C6—H6 | 0.9800 | C18—H18 | 0.9300 |
C7—C8 | 1.524 (7) | C19—C20 | 1.363 (9) |
C7—H7A | 0.9700 | C19—H19 | 0.9300 |
C7—H7B | 0.9700 | C20—C21 | 1.401 (8) |
C8—C13 | 1.360 (8) | C20—H20 | 0.9300 |
C8—C9 | 1.368 (9) | C21—H21 | 0.9300 |
C2—S1—C3 | 92.8 (2) | C13—C8—C7 | 117.3 (6) |
C1—N1—C2 | 116.4 (4) | C9—C8—C7 | 122.9 (6) |
C1—N1—C7 | 121.0 (4) | C8—C9—C10 | 121.7 (8) |
C2—N1—C7 | 121.4 (4) | C8—C9—H9 | 119.1 |
C15—N2—C14 | 108.6 (3) | C10—C9—H9 | 119.1 |
C15—N2—C5 | 111.1 (3) | C11—C10—C9 | 119.0 (9) |
C14—N2—C5 | 109.9 (3) | C11—C10—H10 | 120.5 |
C15—N2—C4 | 110.9 (4) | C9—C10—H10 | 120.5 |
C14—N2—C4 | 111.6 (3) | C10—C11—C12 | 120.3 (9) |
C5—N2—C4 | 104.7 (3) | C10—C11—H11 | 119.9 |
O1—C1—N1 | 124.5 (4) | C12—C11—H11 | 119.9 |
O1—C1—C3 | 122.0 (4) | C11—C12—C13 | 120.9 (9) |
N1—C1—C3 | 113.4 (3) | C11—C12—H12 | 119.5 |
O2—C2—N1 | 124.5 (5) | C13—C12—H12 | 119.5 |
O2—C2—S1 | 124.1 (4) | C8—C13—C12 | 118.6 (8) |
N1—C2—S1 | 111.5 (3) | C8—C13—H13 | 120.7 |
C1—C3—C4 | 113.5 (3) | C12—C13—H13 | 120.7 |
C1—C3—C6 | 108.8 (3) | N2—C14—H14A | 109.5 |
C4—C3—C6 | 104.3 (3) | N2—C14—H14B | 109.5 |
C1—C3—S1 | 105.2 (3) | H14A—C14—H14B | 109.5 |
C4—C3—S1 | 110.5 (3) | N2—C14—H14C | 109.5 |
C6—C3—S1 | 114.8 (3) | H14A—C14—H14C | 109.5 |
N2—C4—C3 | 106.9 (3) | H14B—C14—H14C | 109.5 |
N2—C4—H4A | 110.3 | N2—C15—H15A | 109.5 |
C3—C4—H4A | 110.3 | N2—C15—H15B | 109.5 |
N2—C4—H4B | 110.3 | H15A—C15—H15B | 109.5 |
C3—C4—H4B | 110.3 | N2—C15—H15C | 109.5 |
H4A—C4—H4B | 108.6 | H15A—C15—H15C | 109.5 |
N2—C5—C6 | 103.8 (3) | H15B—C15—H15C | 109.5 |
N2—C5—H5A | 111.0 | C21—C16—C17 | 118.9 (5) |
C6—C5—H5A | 111.0 | C21—C16—C6 | 118.8 (4) |
N2—C5—H5B | 111.0 | C17—C16—C6 | 122.3 (4) |
C6—C5—H5B | 111.0 | C16—C17—C18 | 120.6 (6) |
H5A—C5—H5B | 109.0 | C16—C17—H17 | 119.7 |
C5—C6—C16 | 118.0 (3) | C18—C17—H17 | 119.7 |
C5—C6—C3 | 102.0 (3) | C19—C18—C17 | 119.8 (6) |
C16—C6—C3 | 115.7 (3) | C19—C18—H18 | 120.1 |
C5—C6—H6 | 106.8 | C17—C18—H18 | 120.1 |
C16—C6—H6 | 106.8 | C20—C19—C18 | 120.2 (6) |
C3—C6—H6 | 106.8 | C20—C19—H19 | 119.9 |
N1—C7—C8 | 114.1 (4) | C18—C19—H19 | 119.9 |
N1—C7—H7A | 108.7 | C19—C20—C21 | 120.3 (6) |
C8—C7—H7A | 108.7 | C19—C20—H20 | 119.9 |
N1—C7—H7B | 108.7 | C21—C20—H20 | 119.9 |
C8—C7—H7B | 108.7 | C16—C21—C20 | 120.3 (6) |
H7A—C7—H7B | 107.6 | C16—C21—H21 | 119.9 |
C13—C8—C9 | 119.5 (6) | C20—C21—H21 | 119.9 |
C2—N1—C1—O1 | −173.5 (4) | C1—C3—C6—C5 | 151.1 (3) |
C7—N1—C1—O1 | −5.6 (6) | C4—C3—C6—C5 | 29.6 (4) |
C2—N1—C1—C3 | 10.6 (5) | S1—C3—C6—C5 | −91.4 (3) |
C7—N1—C1—C3 | 178.5 (3) | C1—C3—C6—C16 | −79.6 (4) |
C1—N1—C2—O2 | 173.1 (4) | C4—C3—C6—C16 | 159.0 (4) |
C7—N1—C2—O2 | 5.3 (7) | S1—C3—C6—C16 | 38.0 (5) |
C1—N1—C2—S1 | −7.2 (5) | C1—N1—C7—C8 | 102.8 (5) |
C7—N1—C2—S1 | −175.0 (3) | C2—N1—C7—C8 | −89.9 (6) |
C3—S1—C2—O2 | −179.0 (4) | N1—C7—C8—C13 | −148.3 (5) |
C3—S1—C2—N1 | 1.4 (3) | N1—C7—C8—C9 | 37.7 (8) |
O1—C1—C3—C4 | 54.5 (5) | C13—C8—C9—C10 | 0.4 (11) |
N1—C1—C3—C4 | −129.5 (4) | C7—C8—C9—C10 | 174.2 (7) |
O1—C1—C3—C6 | −61.1 (5) | C8—C9—C10—C11 | 1.8 (14) |
N1—C1—C3—C6 | 114.9 (4) | C9—C10—C11—C12 | −2.4 (16) |
O1—C1—C3—S1 | 175.4 (3) | C10—C11—C12—C13 | 1.0 (17) |
N1—C1—C3—S1 | −8.6 (4) | C9—C8—C13—C12 | −1.8 (10) |
C2—S1—C3—C1 | 3.9 (3) | C7—C8—C13—C12 | −176.0 (6) |
C2—S1—C3—C4 | 126.7 (3) | C11—C12—C13—C8 | 1.2 (13) |
C2—S1—C3—C6 | −115.7 (3) | C5—C6—C16—C21 | −159.5 (4) |
C15—N2—C4—C3 | 100.0 (4) | C3—C6—C16—C21 | 79.4 (5) |
C14—N2—C4—C3 | −138.7 (4) | C5—C6—C16—C17 | 20.9 (6) |
C5—N2—C4—C3 | −19.9 (4) | C3—C6—C16—C17 | −100.2 (5) |
C1—C3—C4—N2 | −124.5 (4) | C21—C16—C17—C18 | −0.8 (7) |
C6—C3—C4—N2 | −6.2 (4) | C6—C16—C17—C18 | 178.7 (4) |
S1—C3—C4—N2 | 117.7 (3) | C16—C17—C18—C19 | −0.8 (8) |
C15—N2—C5—C6 | −80.4 (4) | C17—C18—C19—C20 | 1.3 (10) |
C14—N2—C5—C6 | 159.4 (3) | C18—C19—C20—C21 | 0.0 (11) |
C4—N2—C5—C6 | 39.4 (4) | C17—C16—C21—C20 | 2.1 (8) |
N2—C5—C6—C16 | −170.5 (3) | C6—C16—C21—C20 | −177.5 (5) |
N2—C5—C6—C3 | −42.6 (4) | C19—C20—C21—C16 | −1.7 (10) |
Experimental details
Crystal data | |
Chemical formula | C21H23IN2O2S+·I− |
Mr | 494.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 20.791 (7), 7.606 (3), 13.484 (5) |
β (°) | 90.685 (5) |
V (Å3) | 2132.1 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.62 |
Crystal size (mm) | 0.30 × 0.14 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.675, 0.851 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11395, 4347, 2790 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.104, 1.02 |
No. of reflections | 4347 |
No. of parameters | 247 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.74, −0.47 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
S1—C2 | 1.759 (5) | O1—C1 | 1.215 (5) |
S1—C3 | 1.828 (4) | O2—C2 | 1.214 (5) |
C2—S1—C3 | 92.8 (2) | O2—C2—S1 | 124.1 (4) |
C1—N1—C2 | 116.4 (4) | N1—C2—S1 | 111.5 (3) |
C5—N2—C4 | 104.7 (3) | ||
C6—C3—C4—N2 | −6.2 (4) | C1—C3—C6—C5 | 151.1 (3) |
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Spiro compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are important processes for the construction of spiro compounds (Caramella & Grunanger, 1984). In this paper, the structure of the title compound, (I), is reported. The molecular structure of (I) is illustrated in Fig. 1. A l l bond lengths and angles of (I) are within normal ranges (Table 1).
There is a spiro ring in (I), consisting of pyrrolidine and thiazolidine rings. The pyrrolidine ring C6—C3—C4—N2—C5 is not planar and has an envelope conformation. C6—C3—C4—N2 is nearly planar with the mean deviation from this plane of 0.0304 (3) Å. Atom C5 is 0.6221 (2) Å out from this plane, forming the flap of the envelopes. The dihedral angle between the C6—C5—N2 and C6—C3—C4—N2 planes is 138.4 (4)°, The dihedral angle between the C6—C3—C4—N2 plane and phenyl plane C16—C17—C18—C19—C20—C21 is 111.7 (4) Å. The thiazolidine ring S1—C2—N1—C1—C3 is planar, the mean deviation from this plane is 0.0330 (3) Å. Atoms O1 and O2 deviate by 0.0624 (3) and 0.1308 (3) Å, respectively, from this plane. The dihedral angle between C6—C3—C4—N2 plane of pyrrolidine ring and thiazolidine ring is 94.7 (4)°.