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Logo of actae2this articlesearchopen accesssubmitActa Crystallographica Section E: Crystallographic CommunicationsActa Crystallographica Section E: Crystallographic Communications
 
Acta Crystallogr E Crystallogr Commun. 2017 April 1; 73(Pt 4): 493–499.
Published online 2017 March 10. doi:  10.1107/S205698901700353X
PMCID: PMC5382606

A triclinic polymorph of tri­cyclo­hexyl­phosphane sulfide: crystal structure and Hirshfeld surface analysis

Abstract

The title compound, (C6H11)3PS (systematic name: tri­cyclo­hexyl-λ5-phosphane­thione), is a triclinic (P-1, Z′ = 1) polymorph of the previously reported ortho­rhom­bic form (Pnma, Z′ = 1/2) [Kerr et al. (1977  ). Can. J. Chem. 55, 3081–3085; Reibenspies et al. (1996  ). Z. Kristallogr. 211, 400]. While conformational differences exist between the non-symmetric mol­ecule in the triclinic polymorph, cf. the mirror-symmetric mol­ecule in the ortho­rhom­bic form, these differences are not chemically significant. The major feature of the mol­ecular packing in the triclinic polymorph is the formation of linear chains along the a axis sustained by methine-C—H(...)S(thione) inter­actions. The chains pack with no directional inter­actions between them. The analysis of the Hirshfeld surface for both polymorphs indicates a high degree of similarity, being dominated by H(...)H (ca 90%) and S(...)H/H(...)S contacts.

Keywords: crystal structure, triorganophosphane sulfide, polymorph, Hirshfeld surface analysis

Chemical context  

Recent inter­est in the chemistry of phosphanegold(I) di­thio­carbamate compounds stems from their potential as anti-cancer agents (de Vos et al. 2004  ; Ronconi et al. 2005  ; Gandin et al. 2010  ; Jamaludin et al. 2013  ; Keter et al. 2014  ; Altaf et al. 2015  ). In keeping with the increasing inter­est in gold compounds as potential anti-microbial agents to meet the challenges of microbes developing resistance to available chemotherapies (Glišić & Djuran, 2014  ) and in recognition of the potential of metal di­thio­carbamates as anti-microbial agents (Hogarth, 2012  ), the anti-bacterial properties of phosphanegold(I) di­thio­carbamates have also been explored in recent times (Sim et al., 2014  ; Chen et al., 2016  ). For example, the ‘all-eth­yl’ compound, Et3PAu(S2CNEt2), exhibits broad-range activity against Gram-positive and Gram-negative bacteria and was shown to be bactericidal against methicillin-resistant Staphylococcus aureus (MRSA) (Chen et al., 2016  ). As an extension of these studies, investigations into the anti-microbial potential of related bis­(phosphane)copper(I) di­thio­carbamates and their silver(I) analogues were undertaken, again revealing inter­esting results and dependency of activity upon phosphane- and di­thio­carbamate-bound substituents (Jamaludin et al., 2016  ). During further investigations in this field, the title compound, Cy3P=S (I), was isolated as a decomposition product from a long-term (months) recrystallization of an acetone solution containing (Cy3P)2Ag(S2CNEt2). The crystal and mol­ecular structures of (I) are reported herein and the results compared with those of a previously determined ortho­rhom­bic polymorph, (II) (Kerr et al., 1977  ; Reibenspies et al., 1996  ). Further, a detailed comparison of the Hirshfeld surfaces for (I) and (II) is presented.

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Structural commentary  

The mol­ecular structure of (I), Fig. 1  , features a tetra­hedrally coordinated PV centre defined by a thione-S and three α-carbon atoms of the cyclo­hexyl substituents. The P1—C bond lengths span an experimentally distinct range of 1.8350 (14) to 1.8468 (15) Å, Table 1  . The distortions from the ideal tetra­hedral geometry are relatively minor with the widest angles generally involving the thione-S atom. The cyclo­hexyl rings, each with a chair conformation, adopt orientations so that the methine-H atom is directed towards the thione-S atom in the cases of the C1- and C13-rings, i.e. are syn, with that of the C7-ring being anti.

Figure 1
The mol­ecular structure of polymorph (I), showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
Table 1
Geometric parameters (Å, °) for the triclinic (I) and ortho­rhom­bic (II) polymorphs of Cy3P=S

As mentioned above, the structure of (I) has been reported previously in an ortho­rhom­bic form in two separate determinations (Kerr et al., 1977  ; Reibenspies et al., 1996  ). Data from the more recent determination, measured at 163 K (Reibenspies et al., 1996  ), are included in Table 1  . The major difference in (II) is that the mol­ecule lies on a crystallographic mirror plane; the 2 × syn plus 1 × anti-conformation of the methine-H atoms with respect to the thione-S atom persists. In (II), the P—C bond lengths are equal within experimental error. However, differences are apparent in the bond angles subtended at the PV centre whereby the angles in (II) span a wider range, i.e. 8.5°, cf. 6.3 ° in (I). Also, the widest angle at the P1 atom in (II) is subtended by the symmetry-related cyclo­hexyl rings.

An overlay diagram for (I) and (II) is shown in Fig. 2  , which highlights the coincidence of the cyclo­hexyl ring associated with the methine-H atom having the anti-disposition with respect to the thione-S atom. Clearly, there are conformational differences apparent between the cyclo­hexyl rings related across the pseudo- and crystallographic mirror planes in (I) and (II), respectively.

Figure 2
Overlay diagram of polymorphs (I), red image, and (II), blue image. The mol­ecules are overlapped so the three α-C atoms of the cyclo­hexyl rings are coincident.

Supra­molecular features  

The only directional supra­molecular inter­actions in the crystal of (I) identified in PLATON (Spek, 2009  ) are methine-C—H7(...)S(thione) contacts, i.e. involving the anti-disposed thione-S and methine-H atoms, Table 2  . These lead to a linear chain aligned along the a axis as illustrated in Fig. 3  a. The chains pack with no directional inter­actions between them, Fig. 3  b.

Figure 3
Mol­ecular packing in polymorph (I), showing (a) a linear supra­molecular chain mediated by methine-C—H(...)S(thione) inter­actions aligned along the a axis and (b) a view of the unit-cell contents in projection down ...
Table 2
Hydrogen-bond geometry (Å, °)

In the original report of polymorph (II), it was stated ‘There are no unusual inter-mol­ecular contacts’ (Kerr et al., 1977  ); no comment on the mol­ecular packing was made in the redetermination (Reibenspies et al., 1996  ). As seen from Fig. 4  , supra­molecular zigzag chains are evident in the mol­ecular packing of (II), but these are sustained by weak methyl­ene-C—H(...)S(thione) inter­actions [H(...)Si = 3.027 (2) Å, C(...)Si = 3.938 (2) Å with the angle at H = 159° for (i) 1 + x, y, z] formed on either side of the mirror plane, so the sulfur atom forms two such contacts, and propagate along the a axis.

Figure 4
Mol­ecular packing in polymorph (II), showing a zigzag supra­molecular chain along the a axis mediated by methyl­ene-C—H(...)S(thione) inter­actions, shown as orange dashed lines.

A more detailed analysis of the mol­ecular packing in (I) and (II) is given in Hirshfeld surface analysis.

Hirshfeld surface analysis  

In order to gain more insight into the mol­ecular packing found in (I) and (II), the structures were subjected to a Hirshfeld surface analysis which was performed as described in a recent publication (Jotani et al., 2016  ).

The different shapes of Hirshfeld surfaces mapped over electrostatic potential in Fig. 5  are indicative of the different mol­ecular conformations adopted by the cyclo­hexane rings in (I) and (II). A pair of bright-red spots appearing on the Hirshfeld surface mapped over d norm near methine-H7 and thione-S1 for (I), Fig. 6  , on the extremities of the mol­ecule represent the donor and acceptor of the C—H(...)S inter­action, Table 2  . They are viewed as the respective blue (positive) and red (negative) regions on the Hirshfeld surface mapped over electrostatic potential, Fig. 5  . The absence of characteristic spots on the d norm-mapped Hirshfeld surfaces in the ortho­rhom­bic polymorph (II) (not shown) indicates no similar inter­actions within the sum of the van der Waals radii; see below. The immediate environments about reference mol­ecules of (I) and (II) within the d norm-mapped Hirshfeld surfaces showing inter­molecular C—H(...)S inter­actions are displayed in Fig. 7  a and b, respectively. In the crystal of (II), the zigzag chain of weak inter­molecular methyl­ene-C—H(...)S(thione) contacts on either side of the crystallographic mirror plane is viewed as the pair of red dashed lines in Fig. 7  b (see above).

Figure 5
Views of the Hirshfeld surfaces for mapped over the electrostatic potential in the range ±0.075 au for (a) polymorph (I) and (b) polymorph (II).
Figure 6
Views of the Hirshfeld surface for polymorph (I) mapped over d norm over the range −0.160 to 1.823 au.
Figure 7
Views of the Hirshfeld surfaces mapped over d norm about a reference mol­ecule highlighting inter­molecular C—H(...)S inter­actions and short inter­atomic H(...)H contacts as white and red dashed lines, ...

The overall two-dimensional fingerprint plots for (I) and (II), and those delineated into H(...)H and S(...)H/H(...)S contacts (McKinnon et al., 2007  ) are illustrated in Fig. 8  . It is inter­esting to note that in both polymorphs only sulfur and hydrogen atoms lie on the periphery of the Hirshfeld surfaces and contribute to inter­atomic contacts such as they are; the percentage contributions are as qu­anti­fied in Table 3  . The different relative orientations of the cyclo­hexane rings in the two forms are also evident through the distinct distribution of points in their respective two-dimensional fingerprint plots, Fig. 8  a. In particular for (II), Fig. 8  a, the top region, corresponding to donor inter­actions is stunted with respect to the lower, acceptor region. For (I), a pair of small peaks at d e + d i < 2.4 Å in the fingerprint plot delineated into H(...)H contacts, Fig. 8  b, show the contribution from short inter­atomic H(...)H contacts in the mol­ecular packing, Table 4  . This contrasts the situation for (II), where the pair of peaks occur at d e + d i > 2.4 Å, i.e. at separations greater than the sum of van der Waals radii. The relative strength of the inter­molecular C—H(...)S inter­actions in (I) and (II) are characterized from the fingerprint plots delineated into S(...)H/H(...)S contacts, Fig. 8  c, through the pair of spikes at d e + d i ~ 2.7 Å and d e + d i ~ 3.1 Å, respectively. The asymmetric distribution of points in the fingerprint plot delineated into S(...)H/H(...)S contacts for (II) in Fig. 8  c is the result of the orientation of the cyclo­hexane rings with respect to the crystallographic mirror plane. The upper region, corresponding to donor H(...)S contacts, contributes 4.7% to the surface cf. 6.5% in the lower region, corresponding to S(...)H acceptor contacts.

Figure 8
Fingerprint plots for polymorph (I) and polymorph (II), showing (a) overall and those delineated into (b) H(...)H and (c) S(...)H/H(...)S contacts.
Table 3
Percentage contributions of the different inter­molecular contacts to the Hirshfeld surface in (I) and (II)
Table 4
Short inter­atomic contacts in (I)

The similarity in the mol­ecular packing of (I) and (II) is reflected in the similarity in the physiochemical data collated in Table 5  and calculated in Crystal Explorer (Wolff et al., 2012  ) and PLATON (Spek, 2009  ). While it is noted the values are very close for (I) and (II) (Table 5  ), the volume of the mol­ecule in (I) is slightly greater than that in (II), as is the surface area. However, the mol­ecule in (II) is marginally more globular and reflecting the lack of directional inter­actions between mol­ecules, allowing a closer approach, the density is greater than in (I). Nevertheless, the packing efficiency is marginally greater in (I), probably reflecting the lack of symmetry in the mol­ecule cf. (I).

Table 5
Physiochemical properties for polymorphs (I) and (II)

Database survey  

There are a number of triorganophosphane sulfide structures in the crystallographic literature (Groom et al., 2016  ) with those conforming to the general formula R 3P=S being summarized here. Thus, structures have been described with fractional atomic coordinates, for example with R = Me (Tasker et al., 2005  ), iPr (Staples & Segal, 2001  ), tBu (Steinberger et al., 2001  ), Ph (Foces-Foces & Llamas-Saiz, 1998  ; monoclinic polymorph), Ph (Ziemer et al., 2000  ; triclinic polymorph), 2-tolyl (Cameron & Dahlèn, 1975  ), 3-tolyl (Cameron et al., 1978  ), 4-FPh (Barnes et al., 2007  ), 2-(Me2NCH2)3Ph (Rotar et al., 2010  ), 2,4,6-Me3Ph (Garland et al., 2013  ) and 2,4,6-(OMe)3Ph (Finnen et al., 1994  ). Selected geometric data for these structures along with those for (I) and (II) are collected in Table 6  . The R = Me and iPr mol­ecules have crystallographic mirror symmetry as for (II) whereas the R = tBu compound has crystallographically imposed threefold symmetry. Two polymorphs have been found for R = Ph, and each of these features two independent mol­ecules in the asymmetric unit.

Table 6
Geometric parameters (Å, °) for selected R 3P=S mol­ecules

The longest P=S bond length, i.e. 1.9748 (13) Å, is found in sterically encumbered (2,4,6-Me3Ph)3P=S (Garland et al., 2013  ). That steric effects are not the only factors influencing the magnitude of the P=S bond length is realized in the structure of Me3P=S, with small, electron-donating groups, which has the second longest P=S bond length across the series. The comments on the lack of definitive trends in the S—P—C and C—P—C bond angles made above for (I) and (II) hold true across the series although, generally, the former are wider than the latter. Inter­estingly, in the threefold symmetric tBu3P=S structure, all angles are about 109°.

Synthesis and crystallization  

The title compound (I) is an unexpected product from the in situ reaction of (Cy3P)2AgCl with Na[S2CNEt2] in a 2:1 ratio. The preparation was as follows: Cy3P (Sigma–Aldrich; 0.6 mmol, 0.196 g) dissolved in acetone (20 ml) was added to an acetone solution (20 ml) of AgCl (Sigma–Aldrich; 0.3 mmol, 0.05 g) at room temperature. Then, Na[S2CNEt2] (BDH, 0.3 mmol, 0.08 g) in acetone (20 ml) was added to the reaction mixture followed by stirring for 4 h. The resulting mixture was filtered, covered to exclude light and left for evaporation at room temperature. Colourless crystals were obtained after four months. Yield: 0.132 g (55%), m.p.: 437–440 K. IR (cm−1): ν(P=S) 624 (s).

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 7  . Carbon-bound H atoms were placed in calculated positions (C—H = 0.99–1.00 Å) and were included in the refinement in the riding-model approximation, with U iso(H) set to 1.2U eq(C).

Table 7
Experimental details

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S205698901700353X/hb7665sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901700353X/hb7665Isup2.hkl

CCDC reference: 1536014

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to Sunway University (INT-RRO-2017–096) for supporting this research.

supplementary crystallographic information

Crystal data

C18H33PSZ = 2
Mr = 312.47F(000) = 344
Triclinic, P1Dx = 1.170 Mg m3
a = 6.6400 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.8089 (9) ÅCell parameters from 4800 reflections
c = 12.8818 (10) Åθ = 3.7–29.5°
α = 103.430 (7)°µ = 0.26 mm1
β = 98.467 (7)°T = 100 K
γ = 91.912 (7)°Prism, colourless
V = 887.26 (12) Å30.40 × 0.20 × 0.17 mm

Data collection

Agilent SuperNova, Dual, Mo at zero, AtlasS2 diffractometer4208 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source3739 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.022
ω scansθmax = 29.7°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)h = −8→9
Tmin = 0.926, Tmax = 1.000k = −13→12
8658 measured reflectionsl = −16→17

Refinement

Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.097w = 1/[σ2(Fo2) + (0.0433P)2 + 0.4808P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4208 reflectionsΔρmax = 0.47 e Å3
181 parametersΔρmin = −0.35 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.28983 (5)0.28303 (4)0.60522 (3)0.02266 (11)
P10.58024 (5)0.29616 (3)0.66467 (3)0.01328 (10)
C10.6361 (2)0.17062 (13)0.73806 (11)0.0155 (3)
H10.57110.08980.68770.019*
C20.8619 (2)0.14502 (14)0.76697 (12)0.0176 (3)
H2A0.92690.13000.70120.021*
H2B0.93470.22050.81970.021*
C30.8780 (2)0.02835 (15)0.81546 (12)0.0215 (3)
H3A0.8173−0.04840.75990.026*
H3B1.02380.01570.83710.026*
C40.7689 (2)0.04367 (15)0.91382 (12)0.0215 (3)
H4A0.83960.11430.97270.026*
H4B0.7751−0.03550.94000.026*
C50.5457 (2)0.07171 (15)0.88609 (12)0.0210 (3)
H5A0.4708−0.00330.83370.025*
H5B0.48200.08730.95240.025*
C60.5286 (2)0.18808 (14)0.83768 (12)0.0183 (3)
H6A0.59100.26490.89270.022*
H6B0.38280.20120.81680.022*
C70.7413 (2)0.27103 (13)0.55847 (11)0.0151 (3)
H70.88720.27990.59400.018*
C80.7119 (2)0.37069 (14)0.49033 (12)0.0209 (3)
H8A0.56630.36720.45810.025*
H8B0.74960.45700.53760.025*
C90.8424 (3)0.34686 (15)0.40031 (12)0.0252 (3)
H9A0.81700.41050.35650.030*
H9B0.98860.35710.43250.030*
C100.7926 (3)0.21275 (15)0.32763 (12)0.0254 (3)
H10A0.88100.19840.27100.030*
H10B0.64880.20420.29150.030*
C110.8260 (2)0.11291 (14)0.39418 (12)0.0203 (3)
H11A0.78890.02670.34650.024*
H11B0.97210.11720.42570.024*
C120.6967 (2)0.13517 (14)0.48499 (11)0.0178 (3)
H12A0.72610.07200.52900.021*
H12B0.55030.12240.45320.021*
C130.6633 (2)0.45629 (13)0.75178 (11)0.0155 (3)
H130.66740.51360.70120.019*
C140.5091 (2)0.51104 (15)0.82558 (12)0.0202 (3)
H14A0.37160.50460.78200.024*
H14B0.50270.46090.88040.024*
C150.5722 (2)0.65042 (15)0.88193 (12)0.0219 (3)
H15A0.56890.70140.82710.026*
H15B0.47360.68380.93040.026*
C160.7857 (2)0.66490 (14)0.94750 (12)0.0205 (3)
H16A0.78630.62021.00640.025*
H16B0.82460.75630.98070.025*
C170.9411 (2)0.60985 (15)0.87601 (13)0.0242 (3)
H17A1.07680.61540.92120.029*
H17B0.95160.66090.82220.029*
C180.8796 (2)0.47037 (14)0.81713 (12)0.0200 (3)
H18A0.88460.41750.87060.024*
H18B0.97790.43920.76780.024*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.01585 (19)0.0258 (2)0.0254 (2)0.00077 (14)0.00114 (14)0.00571 (15)
P10.01333 (18)0.01384 (18)0.01275 (17)0.00045 (12)0.00201 (12)0.00351 (13)
C10.0171 (7)0.0152 (7)0.0156 (6)0.0008 (5)0.0049 (5)0.0050 (5)
C20.0175 (7)0.0190 (7)0.0197 (7)0.0038 (5)0.0062 (5)0.0090 (6)
C30.0237 (8)0.0200 (8)0.0248 (8)0.0066 (6)0.0081 (6)0.0101 (6)
C40.0263 (8)0.0204 (8)0.0222 (7)0.0040 (6)0.0074 (6)0.0116 (6)
C50.0240 (8)0.0209 (8)0.0217 (7)0.0008 (6)0.0083 (6)0.0095 (6)
C60.0197 (7)0.0197 (7)0.0189 (7)0.0034 (5)0.0074 (5)0.0084 (6)
C70.0200 (7)0.0129 (7)0.0130 (6)0.0013 (5)0.0047 (5)0.0026 (5)
C80.0334 (8)0.0140 (7)0.0174 (7)0.0034 (6)0.0080 (6)0.0054 (5)
C90.0427 (10)0.0172 (8)0.0207 (7)0.0040 (6)0.0140 (7)0.0089 (6)
C100.0429 (10)0.0208 (8)0.0152 (7)0.0069 (7)0.0094 (6)0.0061 (6)
C110.0293 (8)0.0151 (7)0.0169 (7)0.0029 (6)0.0066 (6)0.0026 (5)
C120.0249 (7)0.0129 (7)0.0165 (7)0.0009 (5)0.0058 (5)0.0039 (5)
C130.0162 (7)0.0158 (7)0.0146 (6)0.0008 (5)0.0029 (5)0.0034 (5)
C140.0166 (7)0.0219 (8)0.0194 (7)0.0024 (5)0.0032 (5)−0.0006 (6)
C150.0252 (8)0.0205 (8)0.0185 (7)0.0075 (6)0.0025 (6)0.0012 (6)
C160.0250 (8)0.0150 (7)0.0194 (7)−0.0003 (5)0.0024 (6)0.0004 (5)
C170.0205 (8)0.0203 (8)0.0282 (8)−0.0052 (6)0.0047 (6)−0.0011 (6)
C180.0164 (7)0.0177 (7)0.0233 (7)−0.0001 (5)0.0028 (6)0.0003 (6)

Geometric parameters (Å, º)

S1—P11.9548 (5)C9—H9A0.9900
P1—C11.8435 (14)C9—H9B0.9900
P1—C71.8350 (14)C10—C111.529 (2)
P1—C131.8468 (15)C10—H10A0.9900
C1—C61.5356 (18)C10—H10B0.9900
C1—C21.5408 (19)C11—C121.5302 (19)
C1—H11.0000C11—H11A0.9900
C2—C31.532 (2)C11—H11B0.9900
C2—H2A0.9900C12—H12A0.9900
C2—H2B0.9900C12—H12B0.9900
C3—C41.530 (2)C13—C181.5376 (19)
C3—H3A0.9900C13—C141.5391 (19)
C3—H3B0.9900C13—H131.0000
C4—C51.530 (2)C14—C151.527 (2)
C4—H4A0.9900C14—H14A0.9900
C4—H4B0.9900C14—H14B0.9900
C5—C61.529 (2)C15—C161.523 (2)
C5—H5A0.9900C15—H15A0.9900
C5—H5B0.9900C15—H15B0.9900
C6—H6A0.9900C16—C171.527 (2)
C6—H6B0.9900C16—H16A0.9900
C7—C81.540 (2)C16—H16B0.9900
C7—C121.5437 (19)C17—C181.533 (2)
C7—H71.0000C17—H17A0.9900
C8—C91.528 (2)C17—H17B0.9900
C8—H8A0.9900C18—H18A0.9900
C8—H8B0.9900C18—H18B0.9900
C9—C101.528 (2)
C7—P1—C1105.82 (6)C10—C9—H9B109.5
C7—P1—C13105.70 (6)C8—C9—H9B109.5
C1—P1—C13111.43 (6)H9A—C9—H9B108.1
C7—P1—S1112.11 (5)C9—C10—C11110.38 (12)
C1—P1—S1109.99 (5)C9—C10—H10A109.6
C13—P1—S1111.60 (5)C11—C10—H10A109.6
C6—C1—C2110.75 (11)C9—C10—H10B109.6
C6—C1—P1111.78 (10)C11—C10—H10B109.6
C2—C1—P1117.32 (10)H10A—C10—H10B108.1
C6—C1—H1105.3C12—C11—C10110.93 (12)
C2—C1—H1105.3C12—C11—H11A109.5
P1—C1—H1105.3C10—C11—H11A109.5
C3—C2—C1110.13 (12)C12—C11—H11B109.5
C3—C2—H2A109.6C10—C11—H11B109.5
C1—C2—H2A109.6H11A—C11—H11B108.0
C3—C2—H2B109.6C11—C12—C7111.43 (12)
C1—C2—H2B109.6C11—C12—H12A109.3
H2A—C2—H2B108.1C7—C12—H12A109.3
C4—C3—C2111.72 (12)C11—C12—H12B109.3
C4—C3—H3A109.3C7—C12—H12B109.3
C2—C3—H3A109.3H12A—C12—H12B108.0
C4—C3—H3B109.3C18—C13—C14110.45 (11)
C2—C3—H3B109.3C18—C13—P1115.68 (10)
H3A—C3—H3B107.9C14—C13—P1113.42 (10)
C3—C4—C5111.30 (12)C18—C13—H13105.4
C3—C4—H4A109.4C14—C13—H13105.4
C5—C4—H4A109.4P1—C13—H13105.4
C3—C4—H4B109.4C15—C14—C13110.25 (12)
C5—C4—H4B109.4C15—C14—H14A109.6
H4A—C4—H4B108.0C13—C14—H14A109.6
C6—C5—C4111.10 (12)C15—C14—H14B109.6
C6—C5—H5A109.4C13—C14—H14B109.6
C4—C5—H5A109.4H14A—C14—H14B108.1
C6—C5—H5B109.4C16—C15—C14111.29 (12)
C4—C5—H5B109.4C16—C15—H15A109.4
H5A—C5—H5B108.0C14—C15—H15A109.4
C5—C6—C1111.04 (12)C16—C15—H15B109.4
C5—C6—H6A109.4C14—C15—H15B109.4
C1—C6—H6A109.4H15A—C15—H15B108.0
C5—C6—H6B109.4C15—C16—C17110.86 (12)
C1—C6—H6B109.4C15—C16—H16A109.5
H6A—C6—H6B108.0C17—C16—H16A109.5
C8—C7—C12110.18 (11)C15—C16—H16B109.5
C8—C7—P1111.69 (10)C17—C16—H16B109.5
C12—C7—P1110.46 (10)H16A—C16—H16B108.1
C8—C7—H7108.1C16—C17—C18111.30 (12)
C12—C7—H7108.1C16—C17—H17A109.4
P1—C7—H7108.1C18—C17—H17A109.4
C9—C8—C7111.28 (12)C16—C17—H17B109.4
C9—C8—H8A109.4C18—C17—H17B109.4
C7—C8—H8A109.4H17A—C17—H17B108.0
C9—C8—H8B109.4C17—C18—C13111.07 (12)
C7—C8—H8B109.4C17—C18—H18A109.4
H8A—C8—H8B108.0C13—C18—H18A109.4
C10—C9—C8110.78 (13)C17—C18—H18B109.4
C10—C9—H9A109.5C13—C18—H18B109.4
C8—C9—H9A109.5H18A—C18—H18B108.0
C7—P1—C1—C6173.93 (10)P1—C7—C8—C9−178.51 (10)
C13—P1—C1—C659.51 (11)C7—C8—C9—C1057.32 (17)
S1—P1—C1—C6−64.79 (10)C8—C9—C10—C11−57.82 (18)
C7—P1—C1—C244.45 (12)C9—C10—C11—C1257.32 (17)
C13—P1—C1—C2−69.97 (12)C10—C11—C12—C7−56.28 (16)
S1—P1—C1—C2165.73 (9)C8—C7—C12—C1154.86 (16)
C6—C1—C2—C356.61 (16)P1—C7—C12—C11178.74 (10)
P1—C1—C2—C3−173.43 (10)C7—P1—C13—C18−67.43 (12)
C1—C2—C3—C4−56.03 (16)C1—P1—C13—C1847.06 (12)
C2—C3—C4—C555.46 (17)S1—P1—C13—C18170.45 (9)
C3—C4—C5—C6−54.99 (17)C7—P1—C13—C14163.46 (10)
C4—C5—C6—C155.98 (16)C1—P1—C13—C14−82.05 (11)
C2—C1—C6—C5−57.02 (16)S1—P1—C13—C1441.34 (11)
P1—C1—C6—C5170.15 (10)C18—C13—C14—C1556.93 (16)
C1—P1—C7—C8−179.57 (10)P1—C13—C14—C15−171.34 (10)
C13—P1—C7—C8−61.26 (11)C13—C14—C15—C16−57.70 (16)
S1—P1—C7—C860.53 (11)C14—C15—C16—C1756.93 (17)
C1—P1—C7—C1257.43 (11)C15—C16—C17—C18−55.49 (18)
C13—P1—C7—C12175.73 (9)C16—C17—C18—C1355.34 (17)
S1—P1—C7—C12−62.47 (10)C14—C13—C18—C17−55.97 (16)
C12—C7—C8—C9−55.35 (16)P1—C13—C18—C17173.48 (10)

Hydrogen-bond geometry (Å, º)

D—H···AD—HH···AD···AD—H···A
C7—H7···S1i1.002.653.5961 (14)157

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

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Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography