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Acta Cryst. (2008). E64, o1683-o1684    [ doi:10.1107/S1600536808024070 ]

Bis(diphenylphosphorothioyl) trisulfide

M. Kulcsar, A. Silvestru and M. Vonas

Abstract top

In the title compound, C24H20P2S5, the P atoms are arranged trans with respect to the S3 group and the S=P-S-S systems have cisoid geometry, with an average S-P-S-S torsion angle of -56.7°. The dihedral angles between the two phenyl rings attached to the P atoms are 87.33 (12) and 75.67 (10)°. In the crystal structure, the molecules are linked into chains running parallel to the a axis by weak intermolecular C-H...S hydrogen bonds. Centrosymmetrically related chains are further connected by [pi]-[pi] stacking interactions, with a centroid-to-centroid distance of 3.795 (5) Å.

Comment top

Our interest was focused for long time on studies concerning reactions between bis(diorganothiophosphoryl)disulfides and diorganodichalcogenides of type R2E2 (E = Se, Te) in order to obtain new organochalcogen compounds with diorganodithiophosphorus ligands (Newton et al., 1993; Silvestru et al., 1994a,b; Drake et al., 2001a,b; Kulcsar et al., 2005; Deleanu et al., 2002). Bis(diorganothiophosphoryl)disulfides attracted much interest also due to their potential applications as pesticides (Fest & Schmidt, 1982), additives in motor oils (Molyneux, 1967) and in the rubber vulcanization (McCleverty et al., 1983). Both alkyl and aryl substituted derivatives of type [R2P(S)S]2 were already structurally characterized, e.g. R = OPr-i (Lawton, 1970; Tkachev et al., 1976; Tiekink, 2001; Zhang et al., 2004), R = OMe, OBu-t (Potrzebowski et al., 1991), cyclohexyl (Buranda et al., 1991), Me, Pr-i (Gallacher & Pinkerton, 1992b), Ph (Gallacher & Pinkerton, 1993), OPh (Gallacher & Pinkerton, 1993; Knopik et al., 1993), menthoxy (Perlikowska et al., 2004), R2 = OCMe2—CMe2O (Yadav et al., 1989), OCMe2—CH2O (Potrzebowski et al., 1994). A search of the Cambridge Structure Database revealed that only for one trisulfide, [Et2P(S)S]2S, the X-ray crystal structure was determined (Gallacher & Pinkerton, 1992a). Here we report about the phenyl substituted analog, [Ph2P(S)S]2S.

The chalcogen atoms S2 and S3 are doubly bonded to phosphorus [S2═P1 = 1.9351 (9); S3═P2 = 1.9303 (9) Å], while the P1—S1 [2.1171 (9) Å] and P2—S4 [2.1282 (9) Å] distances correspond to single P—S bonds (cf. [Ph2P(S)S]2: P═S = 1.930 (1), P—S = 2.139 (1) Å; Gallacher & Pinkerton, 1993). The sulfur–sulfur distances within the S3 group are not significantly different [S5—S4 = 2.0407 (10), S5—S1 = 2.0440 (10) Å], corresponding to a S—S single bond. These values are similar to those found in bis(diorganothiophosphoryl)disulfides or in [Et2P(S)S]2S. The SPS3PS skeleton of the title compound adopts a twisted zigzag chain structure (Fig. 1), with the torsion angles S2—P1—S1—S5 = -56.30 (5)°, P1—S1—S5—S4 = 96.84 (4)°, S1—S5—S4—P2 = 87.42 (5)° and S5—S4—P2—S3 = -57.13 (5)°. Although apparently the conformation of the SPS3PS skeleton is similar to that of the previously reported ethyl derivative, some differences should be noted. In the title compound the phosphorus atoms are trans with respect of the central S3 group [P1—S1···S5—P2 = 171.4°], as are in the related [Et2P(S)S]2S compound (the torsion angle between corresponding atoms is 159.8°). In both cases the central S atom and the terminal S atoms, respectively, are placed on opposite sides of the best plane described by the remaining atoms of the skeleton. However, the S═P···P═S torsion angle is 138.8°, but only -89.4° in the ethyl derivative. Moreover, the S═P—S—S system has a cisoid geometry [S2—P1—S1—S5 = -56.30 (5)°, S5—S4—P2—S3 = -57.13 (5)°], while it has a transoid geometry in [Et2P(S)S]2S (average S═P—S—S torsion angle 179.6°; Gallacher & Pinkerton, 1992a). The S—P—S angles [S2—P1—S1 = 113.77 (4)° and S3—P2—S4 = 114.34 (4)°] are consistent with a cisoid geometry, similar with that found for [Ph2P(S)S]2 [114.44 (4)°; Gallacher & Pinkerton, 1993], but much larger than in the transoid derivatives [(PhO)2P(S)S]2 [108.39 (7)°; Gallacher & Pinkerton, 1993] and [Et2P(S)S]2S [av. 103.7°; Gallacher & Pinkerton, 1992a]. The dihedral angles formed by the plane of the phenyl rings attached to the P1 and P2 atoms are 87.33 (12) 75.67 (10)° respectively. The crystal structure is stabilized by weak intermolecular hydrogen bonding interactions (Emsley, 1994) between the central sulfur atom and an aromatic proton of a neighbouring molecule (Table 1) forming chains parellel to the a axis (Fig. 2). Weak intermolecular S···H contacts were observed in [(PhO)2P(S)S]2 [2.954 (1) Å], but they are absent in [Et2P(S)S]2S or [Ph2P(S)S]2. Centrosymmetrically related chains are further connected by π–π stacking interactions involving the C13–C18 phenyl rings, with centroid-to-centroid distance of 3.795 (5) Å.

Related literature top

For related literature. see: Deleanu et al. (2002); Drake et al. (2001a,b); Gallacher & Pinkerton (1992a, 1992b, 1993); Kulcsar et al. (2005); Newton et al. (1993); Silvestru et al. (1994a,b); Buranda et al. (1991); Fest & Schmidt (1982); Knopik et al. (1993); Lawton (1970); McCleverty et al. (1983); Molyneux (1967); Perlikowska et al. (2004); Potrzebowski et al. (1991, 1994); Tiekink (2001); Tkachev et al. (1976); Zhang et al. (2004); Emsley (1994); Yadav et al. (1989).

Experimental top

The title compound was isolated as a by-product during recrystallization of PhSeS2PPh2 obtained in the reaction between [Ph2P(S)S]2 and Ph2Se2.

Refinement top

All C-bound H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and treated using a riding model with Uiso = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. A view of the title compound, with the atomic numbering scheme, showing displacement ellipsoids at the 50% probability level. H atoms are drawn as spheres of arbitrary radii.
[Figure 2] Fig. 2. View of the S···H intermolecular interactions (dashed lines) in the title compound. Only H involved in hydrogen bonding interactions are shown. Symmetry codes: (i) 1 + x, y, z, (ii) -1 + x, y, z.
Bis(diphenylphosphorothioyl) trisulfide top
Crystal data top
C24H20P2S5Z = 2
Mr = 530.64F000 = 548
Triclinic, P1Dx = 1.387 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.2287 (8) ÅCell parameters from 4229 reflections
b = 11.5476 (10) Åθ = 2.4–25.3º
c = 12.9728 (12) ŵ = 0.59 mm−1
α = 92.690 (2)ºT = 297 (2) K
β = 105.287 (2)ºBlock, yellow
γ = 106.124 (2)º0.35 × 0.27 × 0.21 mm
V = 1270.3 (2) Å3
Data collection top
Bruker SMART APEX
diffractometer		5178 independent reflections
Radiation source: fine-focus sealed tube4536 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
T = 297(2) Kθmax = 26.4º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −11→11
Tmin = 0.819, Tmax = 0.886k = −14→14
13712 measured reflectionsl = −16→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.106  w = 1/[σ2(Fo2) + (0.0406P)2 + 0.4205P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
5178 reflectionsΔρmax = 0.40 e Å−3
280 parametersΔρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C24H20P2S5γ = 106.124 (2)º
Mr = 530.64V = 1270.3 (2) Å3
Triclinic, P1Z = 2
a = 9.2287 (8) ÅMo Kα
b = 11.5476 (10) ŵ = 0.59 mm−1
c = 12.9728 (12) ÅT = 297 (2) K
α = 92.690 (2)º0.35 × 0.27 × 0.21 mm
β = 105.287 (2)º
Data collection top
Bruker SMART APEX
diffractometer		5178 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		4536 reflections with I > 2σ(I)
Tmin = 0.819, Tmax = 0.886Rint = 0.029
13712 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047280 parameters
wR(F2) = 0.106H-atom parameters constrained
S = 1.13Δρmax = 0.40 e Å−3
5178 reflectionsΔρmin = −0.19 e Å−3
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
xyzUiso*/Ueq
C10.2158 (3)0.8016 (2)1.01664 (19)0.0410 (6)
C20.3749 (3)0.8562 (3)1.0317 (2)0.0549 (7)
H20.41410.86410.97240.066*
C30.4758 (4)0.8988 (3)1.1337 (3)0.0649 (8)
H30.58280.93481.14360.078*
C40.4171 (4)0.8878 (3)1.2203 (3)0.0689 (9)
H40.48480.91681.28940.083*
C50.2607 (4)0.8349 (3)1.2068 (2)0.0710 (9)
H50.22250.82831.26650.085*
C60.1586 (3)0.7909 (3)1.1050 (2)0.0561 (7)
H60.05200.75431.09600.067*
C7−0.1095 (3)0.7270 (2)0.8809 (2)0.0432 (6)
C8−0.2183 (3)0.6199 (3)0.8876 (2)0.0541 (7)
H8−0.18770.55000.89800.065*
C9−0.3720 (4)0.6158 (4)0.8789 (3)0.0721 (10)
H9−0.44490.54350.88320.087*
C10−0.4163 (4)0.7184 (5)0.8640 (3)0.0890 (12)
H10−0.52030.71560.85680.107*
C11−0.3101 (5)0.8242 (4)0.8595 (4)0.0986 (13)
H11−0.34120.89410.85130.118*
C12−0.1564 (4)0.8300 (3)0.8671 (3)0.0735 (9)
H12−0.08480.90300.86290.088*
C130.3127 (3)0.3345 (2)0.5892 (2)0.0398 (5)
C140.2557 (3)0.3370 (2)0.4795 (2)0.0479 (6)
H140.15190.33590.44990.057*
C150.3525 (4)0.3410 (3)0.4141 (2)0.0556 (7)
H150.31430.34360.34060.067*
C160.5055 (4)0.3413 (3)0.4577 (3)0.0609 (8)
H160.57050.34300.41350.073*
C170.5620 (3)0.3390 (3)0.5657 (3)0.0619 (8)
H170.66570.33950.59460.074*
C180.4675 (3)0.3360 (2)0.6329 (2)0.0514 (7)
H180.50720.33490.70650.062*
C190.0085 (3)0.2000 (2)0.61159 (19)0.0391 (5)
C200.0029 (3)0.0881 (2)0.6477 (2)0.0553 (7)
H200.08630.08050.70280.066*
C21−0.1260 (4)−0.0116 (3)0.6021 (3)0.0679 (9)
H21−0.1291−0.08660.62610.082*
C22−0.2495 (4)−0.0006 (3)0.5214 (3)0.0663 (9)
H22−0.3370−0.06790.49140.080*
C23−0.2445 (3)0.1094 (3)0.4849 (2)0.0590 (8)
H23−0.32840.11630.42970.071*
C24−0.1155 (3)0.2102 (2)0.5295 (2)0.0468 (6)
H24−0.11230.28460.50420.056*
P10.09047 (8)0.73820 (6)0.88233 (5)0.03962 (16)
P20.18502 (8)0.32528 (6)0.67495 (5)0.03861 (16)
S10.11328 (9)0.56101 (6)0.88821 (5)0.04965 (18)
S20.15246 (9)0.81659 (7)0.76545 (6)0.0581 (2)
S30.27532 (9)0.31611 (7)0.82540 (5)0.0562 (2)
S40.12601 (8)0.48837 (6)0.64407 (5)0.04720 (18)
S5−0.02304 (8)0.48041 (6)0.73690 (6)0.04856 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0431 (14)0.0406 (13)0.0377 (13)0.0128 (11)0.0096 (11)0.0023 (10)
C20.0462 (15)0.0608 (18)0.0556 (17)0.0146 (13)0.0134 (13)0.0027 (14)
C30.0443 (16)0.064 (2)0.072 (2)0.0126 (14)−0.0026 (15)0.0023 (16)
C40.076 (2)0.0575 (19)0.0514 (18)0.0143 (17)−0.0112 (16)−0.0003 (14)
C50.089 (3)0.074 (2)0.0389 (16)0.0113 (19)0.0159 (16)0.0006 (15)
C60.0559 (17)0.0611 (18)0.0435 (15)0.0060 (14)0.0147 (13)0.0017 (13)
C70.0407 (13)0.0489 (15)0.0380 (13)0.0129 (11)0.0096 (11)−0.0008 (11)
C80.0533 (16)0.0624 (18)0.0486 (16)0.0170 (14)0.0183 (13)0.0084 (13)
C90.0529 (18)0.094 (3)0.061 (2)0.0040 (18)0.0249 (16)−0.0066 (18)
C100.055 (2)0.131 (4)0.088 (3)0.040 (2)0.0229 (19)−0.009 (3)
C110.085 (3)0.093 (3)0.137 (4)0.056 (3)0.034 (3)0.007 (3)
C120.067 (2)0.0587 (19)0.103 (3)0.0281 (17)0.0295 (19)0.0056 (18)
C130.0425 (13)0.0311 (12)0.0428 (14)0.0077 (10)0.0113 (11)0.0010 (10)
C140.0475 (15)0.0504 (15)0.0453 (15)0.0136 (12)0.0138 (12)0.0076 (12)
C150.0659 (19)0.0535 (17)0.0465 (16)0.0101 (14)0.0232 (14)0.0062 (13)
C160.0594 (19)0.0526 (17)0.072 (2)0.0048 (14)0.0353 (17)−0.0010 (15)
C170.0399 (15)0.0612 (19)0.078 (2)0.0090 (13)0.0144 (15)−0.0046 (16)
C180.0474 (15)0.0493 (16)0.0510 (16)0.0111 (13)0.0081 (13)−0.0013 (12)
C190.0442 (13)0.0345 (12)0.0406 (13)0.0104 (10)0.0173 (11)0.0027 (10)
C200.0587 (17)0.0399 (15)0.0614 (18)0.0117 (13)0.0107 (14)0.0075 (13)
C210.083 (2)0.0376 (16)0.072 (2)0.0061 (15)0.0157 (18)0.0063 (14)
C220.068 (2)0.0485 (17)0.064 (2)−0.0070 (15)0.0186 (17)−0.0096 (15)
C230.0486 (16)0.0630 (19)0.0515 (17)0.0052 (14)0.0052 (13)−0.0032 (14)
C240.0480 (15)0.0451 (15)0.0454 (15)0.0117 (12)0.0129 (12)0.0061 (12)
P10.0411 (4)0.0412 (4)0.0361 (3)0.0117 (3)0.0113 (3)0.0044 (3)
P20.0440 (4)0.0349 (3)0.0359 (3)0.0113 (3)0.0105 (3)0.0039 (3)
S10.0608 (4)0.0496 (4)0.0432 (4)0.0259 (3)0.0128 (3)0.0062 (3)
S20.0642 (5)0.0640 (5)0.0451 (4)0.0116 (4)0.0206 (3)0.0161 (3)
S30.0658 (5)0.0598 (4)0.0378 (4)0.0173 (4)0.0073 (3)0.0082 (3)
S40.0632 (4)0.0346 (3)0.0467 (4)0.0161 (3)0.0191 (3)0.0064 (3)
S50.0403 (3)0.0436 (4)0.0562 (4)0.0096 (3)0.0097 (3)−0.0040 (3)
Geometric parameters (Å, °) top
C1—C61.380 (4)C14—C151.378 (4)
C1—C21.384 (4)C14—H140.9300
C1—P11.805 (2)C15—C161.375 (4)
C2—C31.377 (4)C15—H150.9300
C2—H20.9300C16—C171.365 (4)
C3—C41.367 (5)C16—H160.9300
C3—H30.9300C17—C181.382 (4)
C4—C51.361 (5)C17—H170.9300
C4—H40.9300C18—H180.9300
C5—C61.380 (4)C19—C241.379 (3)
C5—H50.9300C19—C201.387 (3)
C6—H60.9300C19—P21.816 (2)
C7—C121.379 (4)C20—C211.376 (4)
C7—C81.383 (4)C20—H200.9300
C7—P11.809 (3)C21—C221.369 (4)
C8—C91.381 (4)C21—H210.9300
C8—H80.9300C22—C231.369 (4)
C9—C101.362 (5)C22—H220.9300
C9—H90.9300C23—C241.383 (4)
C10—C111.353 (6)C23—H230.9300
C10—H100.9300C24—H240.9300
C11—C121.378 (5)P1—S21.9351 (9)
C11—H110.9300P1—S12.1171 (9)
C12—H120.9300P2—S31.9303 (9)
C13—C141.385 (3)P2—S42.1282 (9)
C13—C181.386 (4)S1—S52.0440 (10)
C13—P21.808 (2)S4—S52.0407 (10)
C6—C1—C2119.4 (2)C14—C15—H15120.1
C6—C1—P1121.7 (2)C17—C16—C15120.0 (3)
C2—C1—P1118.9 (2)C17—C16—H16120.0
C3—C2—C1120.5 (3)C15—C16—H16120.0
C3—C2—H2119.8C16—C17—C18121.0 (3)
C1—C2—H2119.8C16—C17—H17119.5
C4—C3—C2119.4 (3)C18—C17—H17119.5
C4—C3—H3120.3C17—C18—C13119.1 (3)
C2—C3—H3120.3C17—C18—H18120.4
C5—C4—C3120.8 (3)C13—C18—H18120.4
C5—C4—H4119.6C24—C19—C20119.5 (2)
C3—C4—H4119.6C24—C19—P2123.69 (19)
C4—C5—C6120.4 (3)C20—C19—P2116.8 (2)
C4—C5—H5119.8C21—C20—C19120.1 (3)
C6—C5—H5119.8C21—C20—H20120.0
C1—C6—C5119.6 (3)C19—C20—H20120.0
C1—C6—H6120.2C22—C21—C20120.2 (3)
C5—C6—H6120.2C22—C21—H21119.9
C12—C7—C8118.9 (3)C20—C21—H21119.9
C12—C7—P1117.5 (2)C23—C22—C21120.1 (3)
C8—C7—P1123.5 (2)C23—C22—H22119.9
C9—C8—C7120.5 (3)C21—C22—H22119.9
C9—C8—H8119.8C22—C23—C24120.4 (3)
C7—C8—H8119.8C22—C23—H23119.8
C10—C9—C8119.6 (3)C24—C23—H23119.8
C10—C9—H9120.2C19—C24—C23119.8 (3)
C8—C9—H9120.2C19—C24—H24120.1
C11—C10—C9120.4 (3)C23—C24—H24120.1
C11—C10—H10119.8C1—P1—C7107.49 (11)
C9—C10—H10119.8C1—P1—S2116.30 (9)
C10—C11—C12120.9 (4)C7—P1—S2113.64 (9)
C10—C11—H11119.5C1—P1—S196.94 (8)
C12—C11—H11119.5C7—P1—S1107.14 (9)
C11—C12—C7119.6 (3)S2—P1—S1113.77 (4)
C11—C12—H12120.2C13—P2—C19106.48 (11)
C7—C12—H12120.2C13—P2—S3116.70 (9)
C14—C13—C18119.7 (2)C19—P2—S3113.09 (8)
C14—C13—P2120.46 (19)C13—P2—S497.91 (8)
C18—C13—P2119.8 (2)C19—P2—S4106.85 (8)
C15—C14—C13120.2 (3)S3—P2—S4114.34 (4)
C15—C14—H14119.9S5—S1—P1100.37 (4)
C13—C14—H14119.9S5—S4—P299.52 (4)
C16—C15—C14119.9 (3)S4—S5—S1106.77 (4)
C16—C15—H15120.1
C6—C1—C2—C30.4 (4)C6—C1—P1—C724.6 (3)
P1—C1—C2—C3−176.0 (2)C2—C1—P1—C7−159.0 (2)
C1—C2—C3—C4−0.6 (5)C6—C1—P1—S2153.3 (2)
C2—C3—C4—C50.3 (5)C2—C1—P1—S2−30.4 (2)
C3—C4—C5—C60.3 (5)C6—C1—P1—S1−85.9 (2)
C2—C1—C6—C50.1 (4)C2—C1—P1—S190.5 (2)
P1—C1—C6—C5176.4 (2)C12—C7—P1—C182.6 (2)
C4—C5—C6—C1−0.4 (5)C8—C7—P1—C1−100.7 (2)
C12—C7—C8—C91.0 (4)C12—C7—P1—S2−47.6 (3)
P1—C7—C8—C9−175.7 (2)C8—C7—P1—S2129.2 (2)
C7—C8—C9—C10−0.2 (5)C12—C7—P1—S1−174.1 (2)
C8—C9—C10—C11−1.2 (6)C8—C7—P1—S12.6 (2)
C9—C10—C11—C121.7 (7)C14—C13—P2—C1950.3 (2)
C10—C11—C12—C7−0.9 (6)C18—C13—P2—C19−128.0 (2)
C8—C7—C12—C11−0.4 (5)C14—C13—P2—S3177.66 (17)
P1—C7—C12—C11176.5 (3)C18—C13—P2—S3−0.6 (2)
C18—C13—C14—C15−0.1 (4)C14—C13—P2—S4−59.9 (2)
P2—C13—C14—C15−178.4 (2)C18—C13—P2—S4121.75 (19)
C13—C14—C15—C160.7 (4)C24—C19—P2—C13−82.9 (2)
C14—C15—C16—C17−0.8 (4)C20—C19—P2—C1395.5 (2)
C15—C16—C17—C180.2 (5)C24—C19—P2—S3147.60 (19)
C16—C17—C18—C130.4 (4)C20—C19—P2—S3−34.0 (2)
C14—C13—C18—C17−0.4 (4)C24—C19—P2—S420.9 (2)
P2—C13—C18—C17177.9 (2)C20—C19—P2—S4−160.63 (19)
C24—C19—C20—C21−0.3 (4)C1—P1—S1—S5−179.08 (9)
P2—C19—C20—C21−178.8 (2)C7—P1—S1—S570.17 (9)
C19—C20—C21—C22−0.4 (5)S2—P1—S1—S5−56.30 (5)
C20—C21—C22—C230.8 (5)C13—P2—S4—S5178.76 (8)
C21—C22—C23—C24−0.5 (5)C19—P2—S4—S568.80 (9)
C20—C19—C24—C230.7 (4)S3—P2—S4—S5−57.13 (5)
P2—C19—C24—C23179.1 (2)P2—S4—S5—S187.43 (4)
C22—C23—C24—C19−0.3 (4)P1—S1—S5—S496.84 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17···S5i0.932.943.737 (3)145
Symmetry codes: (i) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17···S5i0.932.943.737 (3)145
Symmetry codes: (i) x+1, y, z.
Acknowledgements top

This work was supported by the Romanian Ministry of Education and Research (CNCSIS grant No. 12/1456/2007). We thank the National Center for X-ray Diffraction (Babes-Bolyai University, Cluj-Napoca) for support in the solid-state structure determination.

references
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