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

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)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.027
• Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.05
           From the CIF: _reflns_number_total               1897
           Count of symmetry unique reflns         1886
           Completeness (_total/calc)            100.58%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured        11
           Fraction of Friedel pairs measured     0.006
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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%.

S3. Refinement

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

Computing details

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

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

Crystal data

C15H15Cl2NO3S3	Dx = 1.532 Mg m^−3
Mr = 424.37	Melting point = 418–420 K
Orthorhombic, P21212	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2 2ab	Cell parameters from 10401 reflections
a = 13.5112 (5) Å	θ = 2.7–25.0°
b = 18.0213 (6) Å	µ = 0.71 mm^−1
c = 7.5559 (2) Å	T = 294 K
V = 1839.78 (10) Å^3	Block, yellow
Z = 4	0.40 × 0.30 × 0.20 mm
F(000) = 872.00

Data collection

Rigaku R-AXIS RAPID S diffractometer	1886 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.034
ω scans	θmax = 25.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→16
Tmin = 0.772, Tmax = 0.869	k = −21→21
69828 measured reflections	l = −8→8
1897 independent reflections

Refinement

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	Chebychev polynomial with 3 parameters (Carruthers & Watkin (1979). Acta Cryst. A35, 698–699) 4.7778 -2.5240 3.7682
wR(F^2) = 0.027	(Δ/σ)max = 0.011
S = 1.13	Δρmax = 0.22 e Å^−3
1886 reflections	Δρmin = −0.20 e Å^−3
217 parameters	Absolute structure: Flack (1983), 11 Friedel pairs
0 restraints	Absolute structure parameter: 0.07 (5)

Special details

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 σ(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 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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, º)

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)