Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001027/ob6022sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001027/ob6022Isup2.hkl |
CCDC reference: 159740
The title compound, (I), was obtained by condensation from NaH-mediated 3,6,9-trioxa-1,11-undecanedithiol and 4-isopropyl-2-(α-tosyloxy-4-nitrobenzyl)tropone (Mori et al., 1992). Single crystals of (I) were obtained by recrystallization from CHCl3.
All H atoms were located at ideal positions and restrained with Uiso held fixed to 1.2 times or 1.5 times (H2O) Ueq of the parent atoms.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Xtal_GX (Hall & du Boulay, 1995); software used to prepare material for publication: SHELXL97.
C25H31NO6S2 | F(000) = 1072 |
Mr = 505.63 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.663 (1) Å | Cell parameters from 20 reflections |
b = 18.862 (2) Å | θ = 10.1–18.0° |
c = 11.363 (1) Å | µ = 0.26 mm−1 |
β = 94.882 (6)° | T = 296 K |
V = 2490.6 (3) Å3 | Prism, yellow |
Z = 4 | 0.3 × 0.2 × 0.2 mm |
Enraf-Nonius FR590 diffractometer | 2259 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 26.3°, θmin = 2.6° |
ω–2θ scans | h = −14→14 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→23 |
Tmin = 0.982, Tmax = 1.000 | l = 0→14 |
5321 measured reflections | 3 standard reflections every 120 min |
5059 independent reflections | intensity decay: 0.6% |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0606P)2 + 0.8224P] where P = (Fo2 + 2Fc2)/3 |
5059 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C25H31NO6S2 | V = 2490.6 (3) Å3 |
Mr = 505.63 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.663 (1) Å | µ = 0.26 mm−1 |
b = 18.862 (2) Å | T = 296 K |
c = 11.363 (1) Å | 0.3 × 0.2 × 0.2 mm |
β = 94.882 (6)° |
Enraf-Nonius FR590 diffractometer | 2259 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.037 |
Tmin = 0.982, Tmax = 1.000 | 3 standard reflections every 120 min |
5321 measured reflections | intensity decay: 0.6% |
5059 independent reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.29 e Å−3 |
5059 reflections | Δρmin = −0.27 e Å−3 |
307 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 | ||
S1 | 0.81595 (9) | −0.01427 (6) | 0.56115 (10) | 0.0506 (3) | |
S2 | 0.46212 (9) | 0.22020 (6) | 0.32535 (11) | 0.0579 (3) | |
O1 | 0.6073 (2) | 0.17902 (16) | 0.5094 (3) | 0.0653 (9) | |
O2 | 0.6767 (3) | −0.08465 (17) | 0.3318 (3) | 0.0685 (9) | |
O3 | 0.4360 (4) | −0.0311 (2) | 0.2020 (3) | 0.1099 (14) | |
O4 | 0.3702 (3) | 0.11006 (19) | 0.1300 (3) | 0.0876 (11) | |
O5 | 1.0530 (3) | 0.2891 (2) | 0.9126 (4) | 0.1081 (14) | |
O6 | 1.1901 (3) | 0.2278 (2) | 0.8541 (3) | 0.1036 (14) | |
N1 | 1.0883 (4) | 0.2428 (2) | 0.8531 (3) | 0.0656 (11) | |
C1 | 0.6497 (3) | 0.1583 (2) | 0.4195 (4) | 0.0456 (10) | |
C2 | 0.7467 (3) | 0.10843 (19) | 0.4312 (3) | 0.0408 (9) | |
C3 | 0.8217 (3) | 0.0921 (2) | 0.3509 (4) | 0.0486 (10) | |
H3 | 0.8797 | 0.0613 | 0.3797 | 0.058* | |
C4 | 0.8300 (3) | 0.1124 (2) | 0.2318 (4) | 0.0482 (10) | |
C5 | 0.7444 (4) | 0.1476 (2) | 0.1657 (4) | 0.0561 (12) | |
H5 | 0.7591 | 0.1557 | 0.0877 | 0.067* | |
C6 | 0.6376 (4) | 0.1735 (2) | 0.1966 (4) | 0.0562 (12) | |
H6 | 0.5888 | 0.1894 | 0.1331 | 0.067* | |
C7 | 0.5938 (3) | 0.1792 (2) | 0.3032 (4) | 0.0452 (10) | |
C8 | 0.9397 (4) | 0.0905 (2) | 0.1787 (4) | 0.0593 (12) | |
H8 | 1.0019 | 0.0978 | 0.2412 | 0.071* | |
C9 | 0.9719 (4) | 0.1331 (3) | 0.0762 (4) | 0.0781 (16) | |
H9A | 1.0433 | 0.1158 | 0.0510 | 0.117* | |
H9B | 0.9805 | 0.1819 | 0.0989 | 0.117* | |
H9C | 0.9128 | 0.1289 | 0.0124 | 0.117* | |
C10 | 0.9374 (4) | 0.0110 (2) | 0.1542 (4) | 0.0735 (14) | |
H10A | 0.9181 | −0.0139 | 0.2234 | 0.110* | |
H10B | 1.0118 | −0.0041 | 0.1337 | 0.110* | |
H10C | 0.8809 | 0.0010 | 0.0899 | 0.110* | |
C11 | 0.7674 (3) | 0.07791 (19) | 0.5566 (3) | 0.0418 (9) | |
H11 | 0.6939 | 0.0796 | 0.5924 | 0.050* | |
C12 | 0.6801 (4) | −0.0610 (2) | 0.5373 (4) | 0.0629 (13) | |
H12A | 0.6947 | −0.1111 | 0.5499 | 0.076* | |
H12B | 0.6309 | −0.0455 | 0.5970 | 0.076* | |
C13 | 0.6148 (4) | −0.0520 (2) | 0.4183 (4) | 0.0626 (13) | |
H13A | 0.5393 | −0.0735 | 0.4186 | 0.075* | |
H13B | 0.6048 | −0.0020 | 0.4005 | 0.075* | |
C14 | 0.6350 (5) | −0.0687 (3) | 0.2141 (4) | 0.0869 (17) | |
H14A | 0.6825 | −0.0934 | 0.1613 | 0.104* | |
H14B | 0.6448 | −0.0183 | 0.2014 | 0.104* | |
C15 | 0.5119 (5) | −0.0872 (3) | 0.1798 (5) | 0.0970 (19) | |
H15A | 0.5029 | −0.0989 | 0.0964 | 0.116* | |
H15B | 0.4914 | −0.1288 | 0.2237 | 0.116* | |
C16 | 0.3625 (5) | −0.0142 (3) | 0.1077 (5) | 0.0846 (16) | |
H16A | 0.3088 | −0.0530 | 0.0920 | 0.101* | |
H16B | 0.4057 | −0.0086 | 0.0391 | 0.101* | |
C17 | 0.2976 (4) | 0.0509 (3) | 0.1246 (5) | 0.0799 (15) | |
H17A | 0.2386 | 0.0566 | 0.0597 | 0.096* | |
H17B | 0.2598 | 0.0475 | 0.1972 | 0.096* | |
C18 | 0.3107 (4) | 0.1729 (3) | 0.1419 (5) | 0.0912 (18) | |
H18A | 0.2554 | 0.1667 | 0.2001 | 0.109* | |
H18B | 0.2685 | 0.1846 | 0.0671 | 0.109* | |
C19 | 0.3905 (4) | 0.2333 (2) | 0.1792 (4) | 0.0663 (13) | |
H19A | 0.3468 | 0.2771 | 0.1782 | 0.080* | |
H19B | 0.4480 | 0.2380 | 0.1228 | 0.080* | |
C20 | 0.8527 (3) | 0.1218 (2) | 0.6332 (3) | 0.0425 (10) | |
C21 | 0.9691 (3) | 0.1202 (2) | 0.6194 (4) | 0.0502 (11) | |
H21 | 0.9961 | 0.0922 | 0.5603 | 0.060* | |
C22 | 1.0461 (4) | 0.1593 (2) | 0.6917 (4) | 0.0549 (11) | |
H22 | 1.1245 | 0.1569 | 0.6826 | 0.066* | |
C23 | 1.0067 (4) | 0.2015 (2) | 0.7762 (4) | 0.0484 (10) | |
C24 | 0.8917 (4) | 0.2062 (2) | 0.7908 (4) | 0.0550 (11) | |
H24 | 0.8656 | 0.2362 | 0.8478 | 0.066* | |
C25 | 0.8148 (4) | 0.1660 (2) | 0.7196 (4) | 0.0528 (11) | |
H25 | 0.7366 | 0.1685 | 0.7297 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0535 (6) | 0.0444 (6) | 0.0535 (7) | 0.0040 (5) | 0.0024 (5) | 0.0071 (6) |
S2 | 0.0490 (7) | 0.0513 (7) | 0.0724 (8) | 0.0109 (5) | −0.0010 (6) | 0.0080 (6) |
O1 | 0.068 (2) | 0.077 (2) | 0.052 (2) | 0.0287 (17) | 0.0085 (16) | −0.0043 (17) |
O2 | 0.067 (2) | 0.078 (2) | 0.059 (2) | 0.0078 (17) | −0.0008 (17) | −0.0060 (18) |
O3 | 0.143 (3) | 0.095 (3) | 0.080 (3) | 0.056 (3) | −0.055 (2) | −0.032 (2) |
O4 | 0.070 (2) | 0.065 (2) | 0.126 (3) | 0.010 (2) | −0.003 (2) | −0.012 (2) |
O5 | 0.112 (3) | 0.103 (3) | 0.105 (3) | 0.000 (3) | −0.012 (2) | −0.057 (3) |
O6 | 0.065 (2) | 0.142 (4) | 0.102 (3) | −0.021 (2) | −0.006 (2) | −0.033 (3) |
N1 | 0.078 (3) | 0.065 (3) | 0.051 (2) | −0.015 (2) | −0.009 (2) | −0.010 (2) |
C1 | 0.043 (2) | 0.041 (2) | 0.052 (3) | −0.0034 (19) | −0.001 (2) | −0.007 (2) |
C2 | 0.039 (2) | 0.036 (2) | 0.047 (2) | 0.0004 (18) | −0.0003 (19) | 0.0020 (19) |
C3 | 0.048 (2) | 0.047 (3) | 0.051 (3) | 0.003 (2) | 0.009 (2) | 0.003 (2) |
C4 | 0.055 (3) | 0.047 (3) | 0.044 (3) | 0.004 (2) | 0.008 (2) | 0.005 (2) |
C5 | 0.063 (3) | 0.067 (3) | 0.039 (2) | −0.002 (2) | 0.011 (2) | 0.003 (2) |
C6 | 0.056 (3) | 0.060 (3) | 0.051 (3) | 0.002 (2) | −0.003 (2) | 0.016 (2) |
C7 | 0.037 (2) | 0.040 (2) | 0.057 (3) | 0.0014 (18) | −0.005 (2) | 0.008 (2) |
C8 | 0.064 (3) | 0.066 (3) | 0.049 (3) | 0.012 (2) | 0.011 (2) | 0.005 (2) |
C9 | 0.081 (4) | 0.072 (4) | 0.085 (4) | 0.000 (3) | 0.031 (3) | 0.008 (3) |
C10 | 0.086 (4) | 0.062 (3) | 0.075 (3) | 0.016 (3) | 0.020 (3) | −0.003 (3) |
C11 | 0.045 (2) | 0.037 (2) | 0.044 (2) | 0.0070 (18) | 0.0069 (18) | 0.0063 (19) |
C12 | 0.068 (3) | 0.055 (3) | 0.067 (3) | −0.011 (2) | 0.015 (3) | 0.006 (2) |
C13 | 0.057 (3) | 0.061 (3) | 0.071 (3) | −0.005 (2) | 0.008 (3) | −0.005 (3) |
C14 | 0.103 (4) | 0.092 (4) | 0.064 (4) | −0.009 (3) | −0.005 (3) | 0.000 (3) |
C15 | 0.104 (5) | 0.079 (4) | 0.100 (5) | 0.019 (4) | −0.037 (4) | −0.031 (3) |
C16 | 0.097 (4) | 0.075 (4) | 0.077 (4) | 0.002 (3) | −0.021 (3) | −0.003 (3) |
C17 | 0.079 (4) | 0.081 (4) | 0.076 (4) | 0.003 (3) | −0.016 (3) | 0.004 (3) |
C18 | 0.074 (4) | 0.085 (4) | 0.109 (5) | 0.012 (3) | −0.024 (3) | −0.007 (4) |
C19 | 0.057 (3) | 0.059 (3) | 0.080 (3) | 0.015 (2) | −0.013 (2) | 0.017 (3) |
C20 | 0.051 (2) | 0.040 (2) | 0.037 (2) | 0.0063 (19) | 0.0042 (19) | 0.005 (2) |
C21 | 0.050 (3) | 0.051 (3) | 0.050 (3) | 0.004 (2) | 0.010 (2) | 0.001 (2) |
C22 | 0.043 (2) | 0.066 (3) | 0.055 (3) | −0.005 (2) | 0.003 (2) | 0.002 (2) |
C23 | 0.059 (3) | 0.043 (2) | 0.042 (3) | 0.001 (2) | 0.001 (2) | 0.003 (2) |
C24 | 0.063 (3) | 0.059 (3) | 0.043 (3) | 0.009 (2) | 0.003 (2) | −0.008 (2) |
C25 | 0.046 (2) | 0.060 (3) | 0.052 (3) | 0.007 (2) | 0.003 (2) | 0.002 (2) |
S1—C12 | 1.813 (4) | C3—C4 | 1.417 (5) |
S1—C11 | 1.828 (4) | C4—C5 | 1.369 (6) |
S2—C7 | 1.756 (4) | C4—C8 | 1.517 (5) |
S2—C19 | 1.811 (4) | C5—C6 | 1.410 (6) |
O1—C1 | 1.236 (4) | C6—C7 | 1.359 (6) |
O2—C13 | 1.409 (5) | C8—C9 | 1.489 (6) |
O2—C14 | 1.417 (5) | C8—C10 | 1.525 (6) |
O3—C16 | 1.352 (5) | C11—C20 | 1.512 (5) |
O3—C15 | 1.416 (6) | C12—C13 | 1.504 (6) |
O4—C18 | 1.386 (6) | C14—C15 | 1.497 (7) |
O4—C17 | 1.399 (6) | C16—C17 | 1.464 (7) |
O5—N1 | 1.198 (5) | C18—C19 | 1.509 (7) |
O6—N1 | 1.219 (5) | C20—C21 | 1.379 (5) |
N1—C23 | 1.462 (5) | C20—C25 | 1.389 (5) |
C1—C2 | 1.469 (5) | C21—C22 | 1.379 (6) |
C1—C7 | 1.476 (5) | C22—C23 | 1.356 (6) |
C2—C3 | 1.352 (5) | C23—C24 | 1.368 (6) |
C2—C11 | 1.537 (5) | C24—C25 | 1.383 (6) |
C12—S1—C11 | 101.1 (2) | C9—C8—C10 | 112.8 (4) |
C7—S2—C19 | 105.6 (2) | C4—C8—C10 | 109.7 (4) |
C13—O2—C14 | 114.2 (4) | C20—C11—C2 | 111.8 (3) |
C16—O3—C15 | 113.5 (4) | C20—C11—S1 | 108.5 (3) |
C18—O4—C17 | 112.3 (4) | C2—C11—S1 | 114.0 (3) |
O5—N1—O6 | 123.0 (4) | C13—C12—S1 | 116.7 (3) |
O5—N1—C23 | 119.3 (4) | O2—C13—C12 | 109.1 (4) |
O6—N1—C23 | 117.7 (4) | O2—C14—C15 | 116.1 (5) |
O1—C1—C2 | 119.1 (4) | O3—C15—C14 | 112.3 (5) |
O1—C1—C7 | 118.6 (4) | O3—C16—C17 | 113.2 (4) |
C2—C1—C7 | 122.0 (4) | O4—C17—C16 | 110.9 (5) |
C3—C2—C1 | 128.5 (4) | O4—C18—C19 | 111.8 (4) |
C3—C2—C11 | 118.8 (3) | C18—C19—S2 | 112.3 (3) |
C1—C2—C11 | 112.5 (3) | C21—C20—C25 | 118.0 (4) |
C2—C3—C4 | 133.1 (4) | C21—C20—C11 | 121.9 (4) |
C5—C4—C3 | 123.3 (4) | C25—C20—C11 | 120.1 (4) |
C5—C4—C8 | 120.9 (4) | C22—C21—C20 | 121.2 (4) |
C3—C4—C8 | 115.8 (4) | C23—C22—C21 | 119.5 (4) |
C4—C5—C6 | 130.6 (4) | C22—C23—C24 | 121.3 (4) |
C7—C6—C5 | 131.0 (4) | C22—C23—N1 | 119.5 (4) |
C6—C7—C1 | 127.3 (4) | C24—C23—N1 | 119.2 (4) |
C6—C7—S2 | 124.2 (3) | C23—C24—C25 | 119.1 (4) |
C1—C7—S2 | 108.3 (3) | C24—C25—C20 | 120.9 (4) |
C9—C8—C4 | 116.3 (4) | ||
O1—C1—C2—C3 | −163.2 (4) | C14—O2—C13—C12 | −169.0 (4) |
C7—C1—C2—C3 | 23.0 (6) | S1—C12—C13—O2 | 67.5 (4) |
O1—C1—C2—C11 | 10.8 (5) | C13—O2—C14—C15 | −57.9 (6) |
C7—C1—C2—C11 | −163.0 (3) | C16—O3—C15—C14 | 128.6 (5) |
C1—C2—C3—C4 | −4.1 (7) | O2—C14—C15—O3 | 89.5 (6) |
C11—C2—C3—C4 | −177.8 (4) | C15—O3—C16—C17 | −170.5 (5) |
C2—C3—C4—C5 | −11.2 (7) | C18—O4—C17—C16 | 177.9 (5) |
C2—C3—C4—C8 | 170.7 (4) | O3—C16—C17—O4 | 67.5 (6) |
C3—C4—C5—C6 | 3.1 (8) | C17—O4—C18—C19 | 165.1 (4) |
C8—C4—C5—C6 | −179.0 (4) | O4—C18—C19—S2 | −64.9 (6) |
C4—C5—C6—C7 | 9.2 (8) | C7—S2—C19—C18 | 93.3 (4) |
C5—C6—C7—C1 | −0.3 (8) | C2—C11—C20—C21 | −74.2 (5) |
C5—C6—C7—S2 | 174.4 (4) | S1—C11—C20—C21 | 52.4 (4) |
O1—C1—C7—C6 | 166.7 (4) | C2—C11—C20—C25 | 105.2 (4) |
C2—C1—C7—C6 | −19.4 (6) | S1—C11—C20—C25 | −128.3 (3) |
O1—C1—C7—S2 | −8.6 (5) | C25—C20—C21—C22 | 2.1 (6) |
C2—C1—C7—S2 | 165.3 (3) | C11—C20—C21—C22 | −178.5 (4) |
C19—S2—C7—C6 | 11.9 (4) | C20—C21—C22—C23 | −1.5 (6) |
C19—S2—C7—C1 | −172.5 (3) | C21—C22—C23—C24 | −0.3 (6) |
C5—C4—C8—C9 | 25.1 (6) | C21—C22—C23—N1 | 179.8 (4) |
C3—C4—C8—C9 | −156.8 (4) | O5—N1—C23—C22 | 166.6 (4) |
C5—C4—C8—C10 | −104.5 (5) | O6—N1—C23—C22 | −13.9 (6) |
C3—C4—C8—C10 | 73.6 (5) | O5—N1—C23—C24 | −13.2 (6) |
C3—C2—C11—C20 | 83.1 (4) | O6—N1—C23—C24 | 166.3 (4) |
C1—C2—C11—C20 | −91.5 (4) | C22—C23—C24—C25 | 1.5 (6) |
C3—C2—C11—S1 | −40.4 (4) | N1—C23—C24—C25 | −178.7 (4) |
C1—C2—C11—S1 | 144.9 (3) | C23—C24—C25—C20 | −0.8 (6) |
C12—S1—C11—C20 | 151.2 (3) | C21—C20—C25—C24 | −0.9 (6) |
C12—S1—C11—C2 | −83.5 (3) | C11—C20—C25—C24 | 179.7 (4) |
C11—S1—C12—C13 | 66.4 (4) |
Experimental details
Crystal data | |
Chemical formula | C25H31NO6S2 |
Mr | 505.63 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 11.663 (1), 18.862 (2), 11.363 (1) |
β (°) | 94.882 (6) |
V (Å3) | 2490.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.3 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Enraf-Nonius FR590 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.982, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5321, 5059, 2259 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.623 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.167, 1.00 |
No. of reflections | 5059 |
No. of parameters | 307 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.27 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, MolEN (Fair, 1990), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), Xtal_GX (Hall & du Boulay, 1995), SHELXL97.
S2—C7 | 1.756 (4) | C3—C4 | 1.417 (5) |
O1—C1 | 1.236 (4) | C4—C5 | 1.369 (6) |
C1—C2 | 1.469 (5) | C5—C6 | 1.410 (6) |
C1—C7 | 1.476 (5) | C6—C7 | 1.359 (6) |
C2—C3 | 1.352 (5) | ||
C3—C4—C8—C9 | −156.8 (4) | O2—C14—C15—O3 | 89.5 (6) |
C3—C4—C8—C10 | 73.6 (5) | C15—O3—C16—C17 | −170.5 (5) |
C12—S1—C11—C2 | −83.5 (3) | C18—O4—C17—C16 | 177.9 (5) |
C11—S1—C12—C13 | 66.4 (4) | O3—C16—C17—O4 | 67.5 (6) |
C14—O2—C13—C12 | −169.0 (4) | C17—O4—C18—C19 | 165.1 (4) |
S1—C12—C13—O2 | 67.5 (4) | O4—C18—C19—S2 | −64.9 (6) |
C13—O2—C14—C15 | −57.9 (6) | C7—S2—C19—C18 | 93.3 (4) |
C16—O3—C15—C14 | 128.6 (5) | C2—C11—C20—C21 | −74.2 (5) |
Mercurophilic dithiocrown derivatives having a troponoid pendant (Mori et al., 1996, 1997; Kubo et al., 1998) were recently prepared since these molecules are excellent carriers of the mercury(II) ion. Particularly noteworthy is, based on their reversible complexation behaviors with mercury(II) salts, the exclusive and selective transport of the mercury(II) ion among various metal ions through a liquid membrane.
As a matter of efficiency in the transport of the mercury(II) ion, the dithiocrown derivatives condensed with a tropone system showed a dependence on the cavity size of the crown ethers (Mori et al., 1996). This was confirmed by the X-ray analyses (Kubo et al., 1995, 1996, 2000a,b; Kato et al., 1995; Mori et al., 1998). In order to reveal the detailed structure of troponoid dithiocrown ether derivatives, the title compound, (I), has been investigated by X-ray analysis.
In (I), the tropone ring (O1 and C1—C7) makes angles of 58.5 (1), 59.6 (1) and 60.0 (2)° with the crown ether ring (defined by S1—S2 and O2—O4), the benzene ring (C20—C25), and the isopropyl group (C8—C10), respectively. The conformation of the ethereal moiety is: C11(g)S1(g)C12(g)C13(t)O2(g)C14(g)C15(t)O3(t)C16(g)C17(t)O4(t)C18(g)C19(t)S2, where t and g denote trans and gauche forms, respectively.
The tropone ring adopts an flattened boat conformation. The angle between the least-squares plane defined by C2/C3/C6/C7 and the plane defined by C3/C4/C5/C6 is 7.7 (3)°. The flattened boat form of the tropone ring was also observed in related compounds. In (I), the angle between the C1/C2/C7 and C2/C3/C6/C7 planes is 16.9 (5)°, which is smaller than that [20.8 (4)°] of 5,8,11-trioxa-2,14-dithiabicyclo[13.4.1]icosa-1(19),15,17-trien-20-one (Kubo et al., 2000a) and that [33.8 (6)°] of 5-oxa-2,8-dithiabicyclo[7.4.1]tetradeca-9,11,13-trien-14-one (Mori et al., 1998). This result suggests that the smaller size of the crown ethers let the deformation of the tropone ring increased.