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Acta Cryst. (2007). E63, o3058    [ doi:10.1107/S1600536807025731 ]

1,1-Dichloro-3-(6,1,3-oxadithiaoctocan-2-ylidene)-3-nitro-2-(4-methylphenylsulfanyl)propene

C. Ibis and N. G. Deniz

Abstract top

The molecule of the title compound, C15H15Cl2NO3S3, is not planar. The butadiene group and the 4-methylphenyl ring are inclined at an angle of 57.9 (1)°.

Comment top

Compounds with conjugated double bonds are fairly reactive because of their strained structures, thus, effective synthesis of these compounds are still challenging in organic chemistry. Macrocyclic thio-crown ethers are particular interest, among other reasons, as potential heavy-metal receptors and could be useful for treatment of heavy-metal poisoning (Edema et al., 1993). The aim of this study was to determine the conformation of the 4,4-dichloro-2-nitro-3-(4-methylphenylsulfanyl)-1,1-(cyclo-oxydiethanesulfanyl) -buta-1,3-diene (Ibis, 1996). The butadiene group and the 4-methylphenyl ring are inclined at an angle of 57.9 (1)°. The butadiene unit has assumed a configuration close to cisoid, but is not completely planar as would be if the two double bounds were fully conjugated. Torsion angle of C4—C3—C2—C1 is −97.2 (3)°.

Related literature top

For general background, see Edema et al. (1993). The C—C bond lengths of the butadiene unit are similar to those in related compounds (Ibis & Deniz, 2006, 2007; Ibis et al., 2006).

For related literature, see: Ibis (1996).

Experimental top

To a mixture of 2-nitro-1,3,4,4-tetrachloro-1-(4-methylphenylthio) −1,3-butadiene (2 g, 5.57 mmol) and 2,2'-oxydiethanethiol, HSCH2CH2OCH2CH2SH, (0.77 g, 5.57 mmol) were stirred in ethanol (35 ml) and 2 g sodium hydroxide in 10 ml water was added at room temperature. The mixture was stirred for 2 h. Chloroform (50 ml) was added to the reaction mixture. The organic layer was separated and washed with water (4x30 ml), and dried MgSO4. The solvent was evaporated and residue was purified by column chromatography on silica gel (0.063–0.20 mm). The yellow crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution at the room temperature; yield 0.60 g, 25%.

Refinement top

H atoms were treated as riding, with C—H = 0.95 (6)Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
1,1-Dichloro-3-(6,1,3-oxadithiaoctocan-2-ylidene)-3-nitro- 2-(4-methylphenylsulfanyl)propene top
Crystal data top
C15H15Cl2NO3S3Dx = 1.532 Mg m−3
Mr = 424.37Melting point: 418-420 K
Orthorhombic, P21212Mo Kα radiation
λ = 0.7107 Å
Hall symbol: P 2 2abCell parameters from 10401 reflections
a = 13.5112 (5) Åθ = 2.7–25.0º
b = 18.0213 (6) ŵ = 0.71 mm−1
c = 7.5559 (2) ÅT = 293.5 K
V = 1839.78 (10) Å3Block, yellow
Z = 40.40 × 0.30 × 0.20 mm
F000 = 872.00
Data collection top
Rigaku R-AXIS RAPID S
diffractometer		1886 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.034
ω scansθmax = 25.1º
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −16→16
Tmin = 0.772, Tmax = 0.869k = −21→21
69828 measured reflectionsl = −8→8
1897 independent reflections
Refinement top
Refinement on F  Chebychev polynomial with 3 parameters (Carruthers & Watkin (1979). Acta Cryst. A35, 698–699) 4.7778 -2.5240 3.7682
R[F2 > 2σ(F2)] = 0.037(Δ/σ)max = 0.011
wR(F2) = 0.027Δρmax = 0.22 e Å−3
S = 1.13Δρmin = −0.20 e Å−3
1886 reflectionsExtinction correction: none
217 parametersAbsolute structure: Flack (1983), 11 Friedel pairs
H atoms treated by a mixture of
independent and constrained refinement		Flack parameter: 0.07 (5)
Crystal data top
C15H15Cl2NO3S3V = 1839.78 (10) Å3
Mr = 424.37Z = 4
Orthorhombic, P21212Mo Kα
a = 13.5112 (5) ŵ = 0.71 mm−1
b = 18.0213 (6) ÅT = 293.5 K
c = 7.5559 (2) Å0.40 × 0.30 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID S
diffractometer		1897 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1886 reflections with F2 > 2σ(F2)
Tmin = 0.772, Tmax = 0.869Rint = 0.034
69828 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.027Δρmax = 0.22 e Å−3
S = 1.13Δρmin = −0.20 e Å−3
1886 reflectionsAbsolute structure: Flack (1983), 11 Friedel pairs
217 parametersFlack parameter: 0.07 (5)
Special details top

Geometry. Least Squares Planes

————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. C1 [1;0;0;0] −0.1475 0.0008 C2 [1;0;0;0] 0.2949 0.0017 C3 [1;0;0;0] −0.3380 0.0019 C4 [1;0;0;0] 0.1243 0.0007

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.2262 angstrom Chi-squared: 30910.697

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. C9 [1;0;0;0] 0.0065 0.0020 C10 [1;0;0;0] −0.0062 0.0022 C11 [1;0;0;0] −0.0039 0.0024 C12 [1;0;0;0] 0.0113 0.0021 C13 [1;0;0;0] −0.0110 0.0023 C14 [1;0;0;0] 0.0007 0.0021

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.0066 angstrom Chi-squared: 36.706

Dihedral angles between least-squares planes ——————————————–

plane plane angle e.s.d. 1 2 57.939 0.179

Refinement. Refinement using reflections with F2 > 3.0 sigma(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S(2)0.91725 (5)0.26150 (4)1.20586 (11)0.0540 (2)
S(1)0.84229 (6)0.44795 (4)1.09641 (10)0.0555 (2)
S(3)0.82153 (6)0.16803 (4)0.91382 (11)0.0616 (2)
Cl(1)0.67918 (7)0.45722 (5)1.38723 (12)0.0775 (3)
Cl(2)0.60463 (6)0.31134 (5)1.2969 (1)0.0780 (3)
O(3)0.8220 (2)0.09720 (12)1.2966 (3)0.0685 (6)
O(2)0.6445 (2)0.36598 (12)0.8510 (3)0.0680 (7)
N(1)0.6947 (2)0.30988 (13)0.8709 (3)0.0550 (7)
C(12)1.0330 (2)0.3895 (1)0.6181 (4)0.0504 (8)
O(1)0.6907 (2)0.25714 (13)0.7694 (3)0.0866 (8)
C(2)0.7595 (2)0.37355 (13)1.1325 (4)0.0452 (7)
C(9)0.9120 (2)0.41788 (13)0.9113 (4)0.0468 (7)
C(11)1.0693 (2)0.3824 (2)0.7885 (4)0.0561 (8)
C(3)0.7635 (2)0.3066 (1)1.0190 (4)0.0446 (7)
C(4)0.8237 (2)0.24795 (13)1.0448 (3)0.0435 (7)
C(14)0.8750 (2)0.4239 (2)0.7403 (4)0.0538 (8)
C(13)0.9349 (2)0.4091 (2)0.5970 (4)0.0566 (8)
C(10)1.0099 (2)0.3963 (2)0.9345 (4)0.0530 (8)
C(1)0.6910 (2)0.3792 (2)1.2578 (4)0.0540 (8)
C(6)0.8883 (3)0.1338 (2)1.4124 (5)0.0684 (10)
C(5)0.8718 (3)0.2166 (2)1.4040 (4)0.0645 (9)
C(7)0.8667 (3)0.0581 (2)1.1558 (5)0.0684 (10)
C(8)0.9115 (2)0.1069 (2)1.0145 (5)0.0623 (9)
C(15)1.0992 (3)0.3795 (2)0.4603 (4)0.0729 (10)
H(1)0.8085 (2)0.4397 (2)0.7242 (4)0.0645*
H(2)0.9074 (2)0.4117 (2)0.4815 (4)0.0680*
H(3)1.1367 (2)0.3693 (2)0.8068 (4)0.0672*
H(4)1.0358 (2)0.3910 (2)1.0507 (4)0.0636*
H(5)0.9025 (3)0.2397 (2)1.5029 (4)0.077*
H(6)0.8022 (3)0.2238 (2)1.4104 (4)0.077*
H(7)0.8786 (3)0.1156 (2)1.5291 (5)0.082*
H(8)0.9545 (3)0.1244 (2)1.3765 (5)0.082*
H(9)0.9401 (2)0.0766 (2)0.9254 (5)0.075*
H(10)0.9615 (2)0.1364 (2)1.0679 (5)0.075*
H(11)0.9164 (3)0.0264 (2)1.2026 (5)0.082*
H(12)0.8166 (3)0.0290 (2)1.1010 (5)0.082*
H(13)1.1272 (3)0.3312 (2)0.4628 (4)0.088*
H(14)1.0614 (3)0.3854 (2)0.3551 (4)0.088*
H(15)1.1506 (3)0.4155 (2)0.4628 (4)0.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S(2)0.0532 (4)0.0441 (3)0.0646 (4)−0.0069 (3)−0.0154 (4)0.0018 (3)
S(1)0.0689 (5)0.0436 (3)0.0540 (4)−0.0054 (3)0.0049 (4)−0.0090 (3)
S(3)0.0740 (5)0.0499 (4)0.0609 (5)0.0050 (3)−0.0072 (4)−0.0153 (4)
Cl(1)0.0919 (6)0.0718 (5)0.0687 (5)0.0196 (5)0.0132 (5)−0.0181 (4)
Cl(2)0.0658 (5)0.0829 (5)0.0854 (6)−0.0053 (4)0.0223 (5)0.0040 (5)
O(3)0.0600 (12)0.0708 (12)0.075 (1)−0.0143 (11)0.0024 (13)−0.0024 (12)
O(2)0.0595 (12)0.0694 (12)0.075 (2)0.0109 (11)−0.0168 (12)0.0018 (11)
N(1)0.056 (1)0.0562 (13)0.053 (1)−0.0019 (11)−0.0094 (12)−0.0043 (12)
C(12)0.052 (2)0.045 (1)0.054 (2)−0.0051 (12)0.002 (1)−0.0044 (13)
O(1)0.106 (2)0.079 (2)0.075 (2)0.013 (1)−0.040 (2)−0.025 (1)
C(2)0.048 (1)0.0429 (13)0.045 (2)0.0031 (11)−0.0034 (13)0.0003 (12)
C(9)0.054 (2)0.0384 (11)0.048 (2)−0.0049 (12)0.000 (1)0.0008 (12)
C(11)0.047 (2)0.060 (2)0.062 (2)−0.0012 (13)−0.006 (2)0.001 (2)
C(3)0.047 (1)0.0446 (13)0.042 (1)−0.0022 (12)−0.0028 (12)−0.0025 (12)
C(4)0.0447 (13)0.0409 (12)0.045 (2)−0.0068 (11)−0.0012 (12)−0.0026 (11)
C(14)0.050 (2)0.054 (2)0.057 (2)0.0027 (13)−0.004 (1)0.001 (1)
C(13)0.064 (2)0.061 (2)0.045 (2)0.001 (1)−0.006 (2)−0.004 (1)
C(10)0.057 (2)0.052 (2)0.050 (2)−0.0083 (13)−0.009 (1)0.0006 (13)
C(1)0.059 (2)0.053 (1)0.050 (2)0.0072 (13)0.007 (1)−0.0019 (12)
C(6)0.079 (2)0.060 (2)0.066 (2)−0.007 (2)−0.012 (2)0.010 (2)
C(5)0.079 (2)0.059 (2)0.055 (2)−0.001 (2)−0.015 (2)0.003 (2)
C(7)0.068 (2)0.045 (2)0.093 (3)−0.003 (1)−0.010 (2)−0.005 (2)
C(8)0.056 (2)0.050 (2)0.081 (2)0.007 (1)0.005 (2)−0.016 (2)
C(15)0.065 (2)0.091 (2)0.062 (2)−0.007 (2)0.008 (2)−0.011 (2)
Geometric parameters (Å, °) top
S(2)—C(4)1.771 (3)C(11)—C(10)1.387 (4)
S(2)—C(5)1.809 (3)C(11)—H(3)0.950 (4)
S(1)—C(2)1.767 (3)C(3)—C(4)1.348 (4)
S(1)—C(9)1.771 (3)C(14)—C(13)1.377 (4)
S(3)—C(4)1.748 (2)C(14)—H(1)0.950 (4)
S(3)—C(8)1.808 (3)C(13)—H(2)0.950 (4)
Cl(1)—C(1)1.720 (3)C(10)—H(4)0.950 (4)
Cl(2)—C(1)1.716 (3)C(6)—C(5)1.510 (4)
O(3)—C(6)1.415 (4)C(6)—H(7)0.950 (5)
O(3)—C(7)1.412 (4)C(6)—H(8)0.950 (5)
O(2)—N(1)1.227 (3)C(5)—H(5)0.950 (5)
N(1)—O(1)1.222 (3)C(5)—H(6)0.950 (5)
N(1)—C(3)1.455 (4)C(7)—C(8)1.510 (5)
C(12)—C(11)1.384 (4)C(7)—H(11)0.950 (5)
C(12)—C(13)1.381 (4)C(7)—H(12)0.950 (5)
C(12)—C(15)1.501 (5)C(8)—H(9)0.950 (5)
C(2)—C(3)1.481 (4)C(8)—H(10)0.950 (4)
C(2)—C(1)1.328 (4)C(15)—H(13)0.950 (5)
C(9)—C(14)1.389 (4)C(15)—H(14)0.950 (5)
C(9)—C(10)1.390 (4)C(15)—H(15)0.950 (5)
C(4)—S(2)—C(5)105.4 (1)Cl(1)—C(1)—Cl(2)114.9 (2)
C(2)—S(1)—C(9)103.1 (1)Cl(1)—C(1)—C(2)122.2 (2)
C(4)—S(3)—C(8)104.6 (1)Cl(2)—C(1)—C(2)122.8 (2)
C(6)—O(3)—C(7)115.4 (2)C(5)—C(6)—H(7)111.1 (4)
O(1)—N(1)—C(3)118.6 (2)C(5)—C(6)—H(8)107.6 (4)
O(1)—N(1)—O(2)122.6 (3)C(5)—C(6)—O(3)110.0 (3)
C(3)—N(1)—O(2)118.8 (2)H(7)—C(6)—H(8)109.5 (5)
C(11)—C(12)—C(13)118.1 (3)H(7)—C(6)—O(3)109.0 (4)
C(11)—C(12)—C(15)121.1 (3)H(8)—C(6)—O(3)109.7 (4)
C(13)—C(12)—C(15)120.7 (3)H(5)—C(5)—H(6)109.5 (4)
C(3)—C(2)—C(1)120.1 (2)H(5)—C(5)—S(2)107.9 (3)
C(3)—C(2)—S(1)120.4 (2)H(5)—C(5)—C(6)109.6 (3)
C(1)—C(2)—S(1)119.5 (2)H(6)—C(5)—S(2)108.5 (3)
C(14)—C(9)—C(10)118.8 (3)H(6)—C(5)—C(6)106.1 (3)
C(14)—C(9)—S(1)121.3 (2)S(2)—C(5)—C(6)115.2 (2)
C(10)—C(9)—S(1)119.5 (2)C(8)—C(7)—H(11)109.3 (4)
C(10)—C(11)—H(3)118.9 (4)C(8)—C(7)—H(12)107.4 (4)
C(10)—C(11)—C(12)121.1 (3)C(8)—C(7)—O(3)114.4 (2)
H(3)—C(11)—C(12)119.9 (4)H(11)—C(7)—H(12)109.5 (4)
C(4)—C(3)—N(1)121.9 (2)H(11)—C(7)—O(3)108.8 (4)
C(4)—C(3)—C(2)125.2 (2)H(12)—C(7)—O(3)107.4 (4)
N(1)—C(3)—C(2)112.9 (2)H(9)—C(8)—H(10)109.5 (4)
S(2)—C(4)—S(3)121.0 (1)H(9)—C(8)—S(3)109.0 (3)
S(2)—C(4)—C(3)115.0 (2)H(9)—C(8)—C(7)109.2 (3)
S(3)—C(4)—C(3)123.6 (2)H(10)—C(8)—S(3)108.4 (3)
C(13)—C(14)—H(1)120.8 (3)H(10)—C(8)—C(7)108.1 (4)
C(13)—C(14)—C(9)120.3 (3)S(3)—C(8)—C(7)112.5 (2)
H(1)—C(14)—C(9)118.8 (3)H(13)—C(15)—H(14)109.5 (5)
H(2)—C(13)—C(12)119.6 (3)H(13)—C(15)—H(15)109.5 (5)
H(2)—C(13)—C(14)118.9 (3)H(13)—C(15)—C(12)109.3 (4)
C(12)—C(13)—C(14)121.5 (3)H(14)—C(15)—H(15)109.5 (5)
H(4)—C(10)—C(9)119.7 (3)H(14)—C(15)—C(12)109.3 (4)
H(4)—C(10)—C(11)120.2 (4)H(15)—C(15)—C(12)109.7 (4)
C(9)—C(10)—C(11)120.1 (3)
C(5)—S(2)—C(4)—S(3)−87.1 (2)S(1)—C(2)—C(1)—Cl(1)0.3 (4)
C(5)—S(2)—C(4)—C(3)100.1 (2)S(1)—C(2)—C(1)—Cl(2)177.5 (2)
C(4)—S(2)—C(5)—C(6)82.4 (3)C(3)—C(2)—C(1)—Cl(1)−177.1 (2)
C(4)—S(2)—C(5)—H(5)−154.9 (3)C(3)—C(2)—C(1)—Cl(2)0.1 (4)
C(4)—S(2)—C(5)—H(6)−36.4 (3)S(1)—C(9)—C(14)—C(13)171.7 (2)
C(9)—S(1)—C(2)—C(3)1.2 (2)S(1)—C(9)—C(14)—H(1)−6.6 (4)
C(9)—S(1)—C(2)—C(1)−176.2 (2)C(10)—C(9)—C(14)—C(13)−0.3 (4)
C(2)—S(1)—C(9)—C(14)80.2 (2)C(10)—C(9)—C(14)—H(1)−178.6 (3)
C(2)—S(1)—C(9)—C(10)−107.8 (2)S(1)—C(9)—C(10)—C(11)−171.2 (2)
C(8)—S(3)—C(4)—S(2)10.9 (2)S(1)—C(9)—C(10)—H(4)9.1 (4)
C(8)—S(3)—C(4)—C(3)−176.9 (2)C(14)—C(9)—C(10)—C(11)1.0 (4)
C(4)—S(3)—C(8)—C(7)89.4 (2)C(14)—C(9)—C(10)—H(4)−178.7 (3)
C(4)—S(3)—C(8)—H(9)−149.3 (3)C(12)—C(11)—C(10)—C(9)0.0 (4)
C(4)—S(3)—C(8)—H(10)−30.2 (4)C(12)—C(11)—C(10)—H(4)179.7 (3)
C(7)—O(3)—C(6)—C(5)116.5 (3)H(3)—C(11)—C(10)—C(9)177.9 (3)
C(7)—O(3)—C(6)—H(7)−121.5 (4)H(3)—C(11)—C(10)—H(4)−2.3 (5)
C(7)—O(3)—C(6)—H(8)−1.7 (4)N(1)—C(3)—C(4)—S(2)168.8 (2)
C(6)—O(3)—C(7)—C(8)−71.2 (3)N(1)—C(3)—C(4)—S(3)−3.8 (4)
C(6)—O(3)—C(7)—H(11)51.4 (4)C(2)—C(3)—C(4)—S(2)−10.8 (4)
C(6)—O(3)—C(7)—H(12)169.7 (3)C(2)—C(3)—C(4)—S(3)176.7 (2)
O(2)—N(1)—C(3)—C(2)2.2 (4)C(9)—C(14)—C(13)—C(12)−1.4 (4)
O(2)—N(1)—C(3)—C(4)−177.3 (3)C(9)—C(14)—C(13)—H(2)177.6 (3)
O(1)—N(1)—C(3)—C(2)−179.1 (2)H(1)—C(14)—C(13)—C(12)176.9 (3)
O(1)—N(1)—C(3)—C(4)1.3 (4)H(1)—C(14)—C(13)—H(2)−4.2 (5)
C(13)—C(12)—C(11)—C(10)−1.7 (4)O(3)—C(6)—C(5)—S(2)−74.0 (4)
C(13)—C(12)—C(11)—H(3)−179.6 (3)O(3)—C(6)—C(5)—H(5)164.1 (4)
C(15)—C(12)—C(11)—C(10)175.8 (3)O(3)—C(6)—C(5)—H(6)46.1 (4)
C(15)—C(12)—C(11)—H(3)−2.1 (5)H(7)—C(6)—C(5)—S(2)165.2 (4)
C(11)—C(12)—C(13)—C(14)2.3 (4)H(7)—C(6)—C(5)—H(5)43.4 (6)
C(11)—C(12)—C(13)—H(2)−176.6 (3)H(7)—C(6)—C(5)—H(6)−74.7 (5)
C(15)—C(12)—C(13)—C(14)−175.1 (3)H(8)—C(6)—C(5)—S(2)45.4 (4)
C(15)—C(12)—C(13)—H(2)6.0 (5)H(8)—C(6)—C(5)—H(5)−76.4 (5)
C(11)—C(12)—C(15)—H(13)58.9 (5)H(8)—C(6)—C(5)—H(6)165.5 (4)
C(11)—C(12)—C(15)—H(14)178.8 (4)O(3)—C(7)—C(8)—S(3)−59.0 (4)
C(11)—C(12)—C(15)—H(15)−61.1 (5)O(3)—C(7)—C(8)—H(9)179.7 (4)
C(13)—C(12)—C(15)—H(13)−123.7 (4)O(3)—C(7)—C(8)—H(10)60.7 (4)
C(13)—C(12)—C(15)—H(14)−3.9 (5)H(11)—C(7)—C(8)—S(3)178.7 (3)
C(13)—C(12)—C(15)—H(15)116.2 (4)H(11)—C(7)—C(8)—H(9)57.5 (5)
S(1)—C(2)—C(3)—N(1)−94.2 (3)H(11)—C(7)—C(8)—H(10)−61.6 (5)
S(1)—C(2)—C(3)—C(4)85.4 (3)H(12)—C(7)—C(8)—S(3)60.0 (4)
C(1)—C(2)—C(3)—N(1)83.2 (3)H(12)—C(7)—C(8)—H(9)−61.2 (5)
C(1)—C(2)—C(3)—C(4)−97.2 (3)H(12)—C(7)—C(8)—H(10)179.8 (4)
Selected geometric parameters (Å, °) top
C(2)—C(3)1.481 (4)C(3)—C(4)1.348 (4)
C(2)—C(1)1.328 (4)
C(3)—C(2)—C(1)120.1 (2)C(4)—C(3)—C(2)125.2 (2)
C(1)—C(2)—C(3)—C(4)−97.2 (3)O(3)—C(7)—C(8)—S(3)−59.0 (4)
O(3)—C(6)—C(5)—S(2)−74.0 (4)
Acknowledgements top

This work was supported by the Research Fund of Istanbul University.

references
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