Bis(diphenyl­phospho­rothio­yl) tris­ulfide

Kulcsar, M.; Silvestru, A.; Vonas, M.

doi:10.1107/S1600536808024070

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1683-o1684

doi:10.1107/S1600536808024070

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Bis(diphenylphosphorothioyl) trisulfide

Monika Kulcsar,^a Anca Silvestru ^a ^* and Marius Vonas ^a

^aFaculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany Janos Street 11, RO-400028 Cluj-Napoca, Romania
^*Correspondence e-mail: ancas@chem.ubbcluj.ro

(Received 14 July 2008; accepted 29 July 2008; online 6 August 2008)

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 π–π stacking interactions, with a centroid-to-centroid distance of 3.795 (5) Å.

Related literature

For related literature. see: Deleanu et al. (2002 ); Drake et al. (2001a ,b ); Gallacher & Pinkerton (1992a ,b , 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

Crystal data

C₂₄H₂₀P₂S₅
M_r = 530.64
Triclinic, $[P \overline 1]$
a = 9.2287 (8) Å
b = 11.5476 (10) Å
c = 12.9728 (12) Å
α = 92.690 (2)°
β = 105.287 (2)°
γ = 106.124 (2)°
V = 1270.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 297 (2) K
0.35 × 0.27 × 0.21 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.819, T_max = 0.885
13712 measured reflections
5178 independent reflections
4536 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.106
S = 1.13
5178 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯S5ⁱ	0.93	2.94	3.737 (3)	145
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024070/rz2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024070/rz2237Isup2.hkl

checkCIF report

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.

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

	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.
	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

C₂₄H₂₀P₂S₅	Z = 2
M_r = 530.64	F(000) = 548
Triclinic, P1	D_x = 1.387 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2287 (8) Å	Cell parameters from 4229 reflections
b = 11.5476 (10) Å	θ = 2.4–25.3°
c = 12.9728 (12) Å	µ = 0.59 mm⁻¹
α = 92.690 (2)°	T = 297 K
β = 105.287 (2)°	Block, yellow
γ = 106.124 (2)°	0.35 × 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 tube	4536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
T_min = 0.819, T_max = 0.886	k = −14→14
13712 measured reflections	l = −16→16

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0406P)² + 0.4205P] where P = (F_o² + 2F_c²)/3
5178 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₄H₂₀P₂S₅	γ = 106.124 (2)°
M_r = 530.64	V = 1270.3 (2) Å³
Triclinic, P1	Z = 2
a = 9.2287 (8) Å	Mo Kα radiation
b = 11.5476 (10) Å	µ = 0.59 mm⁻¹
c = 12.9728 (12) Å	T = 297 K
α = 92.690 (2)°	0.35 × 0.27 × 0.21 mm
β = 105.287 (2)°

Data collection top

Bruker SMART APEX diffractometer	5178 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4536 reflections with I > 2σ(I)
T_min = 0.819, T_max = 0.886	R_int = 0.029
13712 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.13	Δρ_max = 0.40 e Å⁻³
5178 reflections	Δρ_min = −0.19 e Å⁻³
280 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.2158 (3)	0.8016 (2)	1.01664 (19)	0.0410 (6)
C2	0.3749 (3)	0.8562 (3)	1.0317 (2)	0.0549 (7)
H2	0.4141	0.8641	0.9724	0.066*
C3	0.4758 (4)	0.8988 (3)	1.1337 (3)	0.0649 (8)
H3	0.5828	0.9348	1.1436	0.078*
C4	0.4171 (4)	0.8878 (3)	1.2203 (3)	0.0689 (9)
H4	0.4848	0.9168	1.2894	0.083*
C5	0.2607 (4)	0.8349 (3)	1.2068 (2)	0.0710 (9)
H5	0.2225	0.8283	1.2665	0.085*
C6	0.1586 (3)	0.7909 (3)	1.1050 (2)	0.0561 (7)
H6	0.0520	0.7543	1.0960	0.067*
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	−0.1877	0.5500	0.8980	0.065*
C9	−0.3720 (4)	0.6158 (4)	0.8789 (3)	0.0721 (10)
H9	−0.4449	0.5435	0.8832	0.087*
C10	−0.4163 (4)	0.7184 (5)	0.8640 (3)	0.0890 (12)
H10	−0.5203	0.7156	0.8568	0.107*
C11	−0.3101 (5)	0.8242 (4)	0.8595 (4)	0.0986 (13)
H11	−0.3412	0.8941	0.8513	0.118*
C12	−0.1564 (4)	0.8300 (3)	0.8671 (3)	0.0735 (9)
H12	−0.0848	0.9030	0.8629	0.088*
C13	0.3127 (3)	0.3345 (2)	0.5892 (2)	0.0398 (5)
C14	0.2557 (3)	0.3370 (2)	0.4795 (2)	0.0479 (6)
H14	0.1519	0.3359	0.4499	0.057*
C15	0.3525 (4)	0.3410 (3)	0.4141 (2)	0.0556 (7)
H15	0.3143	0.3436	0.3406	0.067*
C16	0.5055 (4)	0.3413 (3)	0.4577 (3)	0.0609 (8)
H16	0.5705	0.3430	0.4135	0.073*
C17	0.5620 (3)	0.3390 (3)	0.5657 (3)	0.0619 (8)
H17	0.6657	0.3395	0.5946	0.074*
C18	0.4675 (3)	0.3360 (2)	0.6329 (2)	0.0514 (7)
H18	0.5072	0.3349	0.7065	0.062*
C19	0.0085 (3)	0.2000 (2)	0.61159 (19)	0.0391 (5)
C20	0.0029 (3)	0.0881 (2)	0.6477 (2)	0.0553 (7)
H20	0.0863	0.0805	0.7028	0.066*
C21	−0.1260 (4)	−0.0116 (3)	0.6021 (3)	0.0679 (9)
H21	−0.1291	−0.0866	0.6261	0.082*
C22	−0.2495 (4)	−0.0006 (3)	0.5214 (3)	0.0663 (9)
H22	−0.3370	−0.0679	0.4914	0.080*
C23	−0.2445 (3)	0.1094 (3)	0.4849 (2)	0.0590 (8)
H23	−0.3284	0.1163	0.4297	0.071*
C24	−0.1155 (3)	0.2102 (2)	0.5295 (2)	0.0468 (6)
H24	−0.1123	0.2846	0.5042	0.056*
P1	0.09047 (8)	0.73820 (6)	0.88233 (5)	0.03962 (16)
P2	0.18502 (8)	0.32528 (6)	0.67495 (5)	0.03861 (16)
S1	0.11328 (9)	0.56101 (6)	0.88821 (5)	0.04965 (18)
S2	0.15246 (9)	0.81659 (7)	0.76545 (6)	0.0581 (2)
S3	0.27532 (9)	0.31611 (7)	0.82540 (5)	0.0562 (2)
S4	0.12601 (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

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0431 (14)	0.0406 (13)	0.0377 (13)	0.0128 (11)	0.0096 (11)	0.0023 (10)
C2	0.0462 (15)	0.0608 (18)	0.0556 (17)	0.0146 (13)	0.0134 (13)	0.0027 (14)
C3	0.0443 (16)	0.064 (2)	0.072 (2)	0.0126 (14)	−0.0026 (15)	0.0023 (16)
C4	0.076 (2)	0.0575 (19)	0.0514 (18)	0.0143 (17)	−0.0112 (16)	−0.0003 (14)
C5	0.089 (3)	0.074 (2)	0.0389 (16)	0.0113 (19)	0.0159 (16)	0.0006 (15)
C6	0.0559 (17)	0.0611 (18)	0.0435 (15)	0.0060 (14)	0.0147 (13)	0.0017 (13)
C7	0.0407 (13)	0.0489 (15)	0.0380 (13)	0.0129 (11)	0.0096 (11)	−0.0008 (11)
C8	0.0533 (16)	0.0624 (18)	0.0486 (16)	0.0170 (14)	0.0183 (13)	0.0084 (13)
C9	0.0529 (18)	0.094 (3)	0.061 (2)	0.0040 (18)	0.0249 (16)	−0.0066 (18)
C10	0.055 (2)	0.131 (4)	0.088 (3)	0.040 (2)	0.0229 (19)	−0.009 (3)
C11	0.085 (3)	0.093 (3)	0.137 (4)	0.056 (3)	0.034 (3)	0.007 (3)
C12	0.067 (2)	0.0587 (19)	0.103 (3)	0.0281 (17)	0.0295 (19)	0.0056 (18)
C13	0.0425 (13)	0.0311 (12)	0.0428 (14)	0.0077 (10)	0.0113 (11)	0.0010 (10)
C14	0.0475 (15)	0.0504 (15)	0.0453 (15)	0.0136 (12)	0.0138 (12)	0.0076 (12)
C15	0.0659 (19)	0.0535 (17)	0.0465 (16)	0.0101 (14)	0.0232 (14)	0.0062 (13)
C16	0.0594 (19)	0.0526 (17)	0.072 (2)	0.0048 (14)	0.0353 (17)	−0.0010 (15)
C17	0.0399 (15)	0.0612 (19)	0.078 (2)	0.0090 (13)	0.0144 (15)	−0.0046 (16)
C18	0.0474 (15)	0.0493 (16)	0.0510 (16)	0.0111 (13)	0.0081 (13)	−0.0013 (12)
C19	0.0442 (13)	0.0345 (12)	0.0406 (13)	0.0104 (10)	0.0173 (11)	0.0027 (10)
C20	0.0587 (17)	0.0399 (15)	0.0614 (18)	0.0117 (13)	0.0107 (14)	0.0075 (13)
C21	0.083 (2)	0.0376 (16)	0.072 (2)	0.0061 (15)	0.0157 (18)	0.0063 (14)
C22	0.068 (2)	0.0485 (17)	0.064 (2)	−0.0070 (15)	0.0186 (17)	−0.0096 (15)
C23	0.0486 (16)	0.0630 (19)	0.0515 (17)	0.0052 (14)	0.0052 (13)	−0.0032 (14)
C24	0.0480 (15)	0.0451 (15)	0.0454 (15)	0.0117 (12)	0.0129 (12)	0.0061 (12)
P1	0.0411 (4)	0.0412 (4)	0.0361 (3)	0.0117 (3)	0.0113 (3)	0.0044 (3)
P2	0.0440 (4)	0.0349 (3)	0.0359 (3)	0.0113 (3)	0.0105 (3)	0.0039 (3)
S1	0.0608 (4)	0.0496 (4)	0.0432 (4)	0.0259 (3)	0.0128 (3)	0.0062 (3)
S2	0.0642 (5)	0.0640 (5)	0.0451 (4)	0.0116 (4)	0.0206 (3)	0.0161 (3)
S3	0.0658 (5)	0.0598 (4)	0.0378 (4)	0.0173 (4)	0.0073 (3)	0.0082 (3)
S4	0.0632 (4)	0.0346 (3)	0.0467 (4)	0.0161 (3)	0.0191 (3)	0.0064 (3)
S5	0.0403 (3)	0.0436 (4)	0.0562 (4)	0.0096 (3)	0.0097 (3)	−0.0040 (3)

Geometric parameters (Å, º) top

C1—C6	1.380 (4)	C14—C15	1.378 (4)
C1—C2	1.384 (4)	C14—H14	0.9300
C1—P1	1.805 (2)	C15—C16	1.375 (4)
C2—C3	1.377 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.365 (4)
C3—C4	1.367 (5)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.382 (4)
C4—C5	1.361 (5)	C17—H17	0.9300
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.380 (4)	C19—C24	1.379 (3)
C5—H5	0.9300	C19—C20	1.387 (3)
C6—H6	0.9300	C19—P2	1.816 (2)
C7—C12	1.379 (4)	C20—C21	1.376 (4)
C7—C8	1.383 (4)	C20—H20	0.9300
C7—P1	1.809 (3)	C21—C22	1.369 (4)
C8—C9	1.381 (4)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.369 (4)
C9—C10	1.362 (5)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.383 (4)
C10—C11	1.353 (6)	C23—H23	0.9300
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.378 (5)	P1—S2	1.9351 (9)
C11—H11	0.9300	P1—S1	2.1171 (9)
C12—H12	0.9300	P2—S3	1.9303 (9)
C13—C14	1.385 (3)	P2—S4	2.1282 (9)
C13—C18	1.386 (4)	S1—S5	2.0440 (10)
C13—P2	1.808 (2)	S4—S5	2.0407 (10)

C6—C1—C2	119.4 (2)	C14—C15—H15	120.1
C6—C1—P1	121.7 (2)	C17—C16—C15	120.0 (3)
C2—C1—P1	118.9 (2)	C17—C16—H16	120.0
C3—C2—C1	120.5 (3)	C15—C16—H16	120.0
C3—C2—H2	119.8	C16—C17—C18	121.0 (3)
C1—C2—H2	119.8	C16—C17—H17	119.5
C4—C3—C2	119.4 (3)	C18—C17—H17	119.5
C4—C3—H3	120.3	C17—C18—C13	119.1 (3)
C2—C3—H3	120.3	C17—C18—H18	120.4
C5—C4—C3	120.8 (3)	C13—C18—H18	120.4
C5—C4—H4	119.6	C24—C19—C20	119.5 (2)
C3—C4—H4	119.6	C24—C19—P2	123.69 (19)
C4—C5—C6	120.4 (3)	C20—C19—P2	116.8 (2)
C4—C5—H5	119.8	C21—C20—C19	120.1 (3)
C6—C5—H5	119.8	C21—C20—H20	120.0
C1—C6—C5	119.6 (3)	C19—C20—H20	120.0
C1—C6—H6	120.2	C22—C21—C20	120.2 (3)
C5—C6—H6	120.2	C22—C21—H21	119.9
C12—C7—C8	118.9 (3)	C20—C21—H21	119.9
C12—C7—P1	117.5 (2)	C23—C22—C21	120.1 (3)
C8—C7—P1	123.5 (2)	C23—C22—H22	119.9
C9—C8—C7	120.5 (3)	C21—C22—H22	119.9
C9—C8—H8	119.8	C22—C23—C24	120.4 (3)
C7—C8—H8	119.8	C22—C23—H23	119.8
C10—C9—C8	119.6 (3)	C24—C23—H23	119.8
C10—C9—H9	120.2	C19—C24—C23	119.8 (3)
C8—C9—H9	120.2	C19—C24—H24	120.1
C11—C10—C9	120.4 (3)	C23—C24—H24	120.1
C11—C10—H10	119.8	C1—P1—C7	107.49 (11)
C9—C10—H10	119.8	C1—P1—S2	116.30 (9)
C10—C11—C12	120.9 (4)	C7—P1—S2	113.64 (9)
C10—C11—H11	119.5	C1—P1—S1	96.94 (8)
C12—C11—H11	119.5	C7—P1—S1	107.14 (9)
C11—C12—C7	119.6 (3)	S2—P1—S1	113.77 (4)
C11—C12—H12	120.2	C13—P2—C19	106.48 (11)
C7—C12—H12	120.2	C13—P2—S3	116.70 (9)
C14—C13—C18	119.7 (2)	C19—P2—S3	113.09 (8)
C14—C13—P2	120.46 (19)	C13—P2—S4	97.91 (8)
C18—C13—P2	119.8 (2)	C19—P2—S4	106.85 (8)
C15—C14—C13	120.2 (3)	S3—P2—S4	114.34 (4)
C15—C14—H14	119.9	S5—S1—P1	100.37 (4)
C13—C14—H14	119.9	S5—S4—P2	99.52 (4)
C16—C15—C14	119.9 (3)	S4—S5—S1	106.77 (4)
C16—C15—H15	120.1

C6—C1—C2—C3	0.4 (4)	C6—C1—P1—C7	24.6 (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—S2	153.3 (2)
C2—C3—C4—C5	0.3 (5)	C2—C1—P1—S2	−30.4 (2)
C3—C4—C5—C6	0.3 (5)	C6—C1—P1—S1	−85.9 (2)
C2—C1—C6—C5	0.1 (4)	C2—C1—P1—S1	90.5 (2)
P1—C1—C6—C5	176.4 (2)	C12—C7—P1—C1	82.6 (2)
C4—C5—C6—C1	−0.4 (5)	C8—C7—P1—C1	−100.7 (2)
C12—C7—C8—C9	1.0 (4)	C12—C7—P1—S2	−47.6 (3)
P1—C7—C8—C9	−175.7 (2)	C8—C7—P1—S2	129.2 (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—S1	2.6 (2)
C9—C10—C11—C12	1.7 (7)	C14—C13—P2—C19	50.3 (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—S3	177.66 (17)
P1—C7—C12—C11	176.5 (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—S4	121.75 (19)
C13—C14—C15—C16	0.7 (4)	C24—C19—P2—C13	−82.9 (2)
C14—C15—C16—C17	−0.8 (4)	C20—C19—P2—C13	95.5 (2)
C15—C16—C17—C18	0.2 (5)	C24—C19—P2—S3	147.60 (19)
C16—C17—C18—C13	0.4 (4)	C20—C19—P2—S3	−34.0 (2)
C14—C13—C18—C17	−0.4 (4)	C24—C19—P2—S4	20.9 (2)
P2—C13—C18—C17	177.9 (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—S5	70.17 (9)
C19—C20—C21—C22	−0.4 (5)	S2—P1—S1—S5	−56.30 (5)
C20—C21—C22—C23	0.8 (5)	C13—P2—S4—S5	178.76 (8)
C21—C22—C23—C24	−0.5 (5)	C19—P2—S4—S5	68.80 (9)
C20—C19—C24—C23	0.7 (4)	S3—P2—S4—S5	−57.13 (5)
P2—C19—C24—C23	179.1 (2)	P2—S4—S5—S1	87.43 (4)
C22—C23—C24—C19	−0.3 (4)	P1—S1—S5—S4	96.84 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···S5ⁱ	0.93	2.94	3.737 (3)	145

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀P₂S₅
M_r	530.64
Crystal system, space group	Triclinic, P1
Temperature (K)	297
a, b, c (Å)	9.2287 (8), 11.5476 (10), 12.9728 (12)
α, β, γ (°)	92.690 (2), 105.287 (2), 106.124 (2)
V (Å³)	1270.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.35 × 0.27 × 0.21

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.819, 0.886
No. of measured, independent and observed [I > 2σ(I)] reflections	13712, 5178, 4536
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.106, 1.13
No. of reflections	5178
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.19

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2006), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···S5ⁱ	0.93	2.94	3.737 (3)	145

Symmetry code: (i) x+1, y, z.

Acknowledgements

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.

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