Bis[O-isopropyl (4-eth-oxy-phen-yl)dithio-phospho-nato-κ(2) S,S']lead(II).

The title compound, [Pb(C11H16O2PS2)2], is a neutral four-coordinate mononuclear complex with a distorted square-pyramidal geometry of the PbS4 core. The apical Pb(II) atom of each pyramid is 1.33059 (3) Å above the basal S4 plane. The metal atom is surrounded by two chelating dithio-phospho-nate ligands binding through the S-donor atoms. The ligands are anisobidentate as the pyramid is comprised of Pb-S bond lengths that vary substanti-ally [2.6999 (7), 2.7128 (6), 2.8877 (7) and 2.9472 (7) Å], clearly indicating two short and two longer bond lengths. The P-S bond lengths are also paired as shorter [1.9959 (9) and 1.9877 (8) Å] and slightly longer [2.0115 (9) and 2.0245 (9) Å], indicating an anisobidentate nature of the ligand whereby the shorter P-S bond has more double-bond character than the other. The S-Pb-S (chelating) bond angles range from 71.841 (18) to 72.692 (19)°, whilst the Pb-S-P bond angles range from 84.70 (3) to 90.51 (3)°.

Related literature

For information on dithio­phospho­nate compounds, see: Van Zyl & Fackler (2000 ▶); Van Zyl (2010 ▶). For similar lead(II) dithio­phospho­nate complexes, see: Gray et al. (2003 ▶, 2004 ▶).

Experimental

Crystal data

[Pb(C11H16O2PS2)2]

M = 757.85

Triclinic,

a = 10.2092 (8) Å

b = 11.7016 (10) Å

c = 12.9915 (10) Å

α = 89.297 (2)°

β = 85.016 (2)°

γ = 69.034 (1)°

V = 1443.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 6.27 mm−1

T = 173 K

0.16 × 0.14 × 0.11 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.434, T max = 0.546

36710 measured reflections

7212 independent reflections

6564 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.045

S = 1.03

7212 reflections

304 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046818/gk2529sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046818/gk2529Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Pb(C11H16O2PS2)2]	Z = 2
Mr = 757.85	F(000) = 744
Triclinic, P1	?e
Hall symbol: -P 1	Dx = 1.744 Mg m−3
a = 10.2092 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7016 (10) Å	Cell parameters from 36710 reflections
c = 12.9915 (10) Å	θ = 1.6–28.4°
α = 89.297 (2)°	µ = 6.27 mm−1
β = 85.016 (2)°	T = 173 K
γ = 69.034 (1)°	Block, colourless
V = 1443.5 (2) Å3	0.16 × 0.14 × 0.11 mm

Bruker Kappa DUO APEXII diffractometer	7212 independent reflections
Radiation source: fine-focus sealed tube	6564 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
0.5° φ scans and ω scans	θmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.434, Tmax = 0.546	k = −15→15
36710 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020	H-atom parameters constrained
wR(F2) = 0.045	w = 1/[σ2(Fo2) + (0.0234P)2 + 0.042P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.002
7212 reflections	Δρmax = 0.61 e Å−3
304 parameters	Δρmin = −0.63 e Å−3
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Pb1	0.563161 (9)	0.892734 (7)	0.676272 (7)	0.02692 (3)
S1	0.48642 (6)	0.83844 (6)	0.47888 (5)	0.03000 (13)
S2	0.80447 (7)	0.77787 (6)	0.55716 (5)	0.03150 (13)
S3	0.55200 (7)	0.68031 (6)	0.75505 (5)	0.03173 (14)
S4	0.75140 (7)	0.82120 (5)	0.84420 (5)	0.03020 (13)
P1	0.69313 (6)	0.77422 (5)	0.43769 (5)	0.02499 (13)
P2	0.67269 (7)	0.68943 (5)	0.86809 (5)	0.02494 (13)
O1	0.8185 (2)	1.06377 (17)	0.08990 (14)	0.0368 (4)
O2	0.74190 (18)	0.64074 (14)	0.38776 (13)	0.0314 (4)
O3	0.31553 (18)	0.75446 (15)	1.26420 (13)	0.0315 (4)
O4	0.79180 (18)	0.55982 (14)	0.88024 (13)	0.0299 (4)
C1	0.7390 (2)	0.8566 (2)	0.33187 (18)	0.0244 (5)
C2	0.7854 (2)	0.9519 (2)	0.35221 (19)	0.0280 (5)
H2	0.7992	0.9676	0.4213	0.034*
C3	0.8118 (3)	1.0243 (2)	0.27399 (19)	0.0295 (5)
H3	0.8416	1.0898	0.2894	0.035*
C4	0.7941 (3)	1.0000 (2)	0.17254 (19)	0.0293 (5)
C5	0.7474 (3)	0.9048 (2)	0.15114 (19)	0.0294 (5)
H5	0.7350	0.8885	0.0819	0.035*
C6	0.7191 (3)	0.8344 (2)	0.22993 (18)	0.0276 (5)
H6	0.6861	0.7707	0.2148	0.033*
C7	0.8657 (3)	1.1634 (3)	0.1081 (2)	0.0438 (7)
H7A	0.9567	1.1329	0.1394	0.053*
H7B	0.7958	1.2251	0.1558	0.053*
C8	0.8824 (4)	1.2188 (3)	0.0058 (2)	0.0507 (8)
H8A	0.9426	1.1547	−0.0432	0.076*
H8B	0.9257	1.2803	0.0139	0.076*
H8C	0.7898	1.2578	−0.0203	0.076*
C9	0.7074 (3)	0.5436 (2)	0.4444 (2)	0.0361 (6)
H9	0.6554	0.5776	0.5125	0.043*
C10	0.6158 (4)	0.5027 (3)	0.3833 (3)	0.0567 (9)
H10A	0.5333	0.5735	0.3681	0.085*
H10B	0.5850	0.4437	0.4230	0.085*
H10C	0.6684	0.4639	0.3185	0.085*
C11	0.8454 (4)	0.4454 (3)	0.4627 (3)	0.0702 (11)
H11A	0.8952	0.4093	0.3962	0.105*
H11B	0.8281	0.3817	0.5054	0.105*
H11C	0.9029	0.4810	0.4983	0.105*
C12	0.5720 (3)	0.7089 (2)	0.99137 (18)	0.0251 (5)
C13	0.4855 (3)	0.8252 (2)	1.02436 (19)	0.0294 (5)
H13	0.4853	0.8933	0.9837	0.035*
C14	0.3992 (3)	0.8444 (2)	1.11533 (19)	0.0297 (5)
H14	0.3414	0.9251	1.1376	0.036*
C15	0.3976 (3)	0.7450 (2)	1.17388 (18)	0.0269 (5)
C16	0.4827 (3)	0.6269 (2)	1.14110 (19)	0.0307 (5)
H16	0.4811	0.5588	1.1811	0.037*
C17	0.5694 (3)	0.6088 (2)	1.05057 (19)	0.0297 (5)
H17	0.6275	0.5281	1.0283	0.036*
C18	0.2206 (3)	0.8742 (2)	1.2982 (2)	0.0331 (6)
H18A	0.1523	0.9098	1.2464	0.040*
H18B	0.2738	0.9290	1.3069	0.040*
C19	0.1447 (3)	0.8615 (2)	1.3993 (2)	0.0375 (6)
H19A	0.0849	0.8141	1.3885	0.056*
H19B	0.0861	0.9429	1.4273	0.056*
H19C	0.2134	0.8193	1.4481	0.056*
C20	0.9080 (3)	0.5123 (2)	0.79867 (19)	0.0305 (5)
H20	0.8964	0.5734	0.7425	0.037*
C21	0.9019 (3)	0.3954 (2)	0.7559 (2)	0.0418 (7)
H21A	0.9166	0.3347	0.8105	0.063*
H21B	0.9756	0.3638	0.6990	0.063*
H21C	0.8095	0.4117	0.7304	0.063*
C22	1.0424 (3)	0.4935 (3)	0.8471 (3)	0.0529 (8)
H22A	1.0400	0.5717	0.8750	0.079*
H22B	1.1225	0.4615	0.7948	0.079*
H22C	1.0525	0.4349	0.9032	0.079*

	U11	U22	U33	U12	U13	U23
Pb1	0.02779 (5)	0.02345 (5)	0.02595 (5)	−0.00485 (3)	−0.00277 (4)	0.00404 (3)
S1	0.0212 (3)	0.0358 (3)	0.0304 (3)	−0.0072 (2)	−0.0021 (2)	0.0031 (2)
S2	0.0231 (3)	0.0399 (3)	0.0279 (3)	−0.0064 (2)	−0.0058 (2)	0.0074 (3)
S3	0.0417 (4)	0.0317 (3)	0.0279 (3)	−0.0191 (3)	−0.0099 (3)	0.0051 (2)
S4	0.0366 (4)	0.0277 (3)	0.0305 (3)	−0.0156 (3)	−0.0072 (3)	0.0037 (2)
P1	0.0224 (3)	0.0250 (3)	0.0244 (3)	−0.0050 (2)	−0.0013 (2)	0.0044 (2)
P2	0.0297 (3)	0.0213 (3)	0.0233 (3)	−0.0084 (2)	−0.0036 (2)	0.0030 (2)
O1	0.0457 (11)	0.0417 (10)	0.0306 (10)	−0.0245 (9)	−0.0069 (8)	0.0114 (8)
O2	0.0349 (10)	0.0250 (8)	0.0300 (9)	−0.0067 (7)	0.0021 (8)	0.0039 (7)
O3	0.0326 (10)	0.0268 (8)	0.0324 (10)	−0.0093 (7)	0.0048 (8)	−0.0016 (7)
O4	0.0327 (10)	0.0239 (8)	0.0265 (9)	−0.0035 (7)	0.0023 (7)	0.0038 (7)
C1	0.0196 (11)	0.0246 (11)	0.0244 (12)	−0.0028 (8)	−0.0013 (9)	0.0046 (9)
C2	0.0258 (13)	0.0320 (12)	0.0251 (12)	−0.0086 (10)	−0.0040 (10)	0.0018 (9)
C3	0.0290 (13)	0.0303 (12)	0.0322 (13)	−0.0139 (10)	−0.0052 (11)	0.0027 (10)
C4	0.0263 (13)	0.0306 (12)	0.0297 (13)	−0.0090 (10)	−0.0020 (10)	0.0088 (10)
C5	0.0316 (14)	0.0305 (12)	0.0249 (12)	−0.0093 (10)	−0.0043 (10)	0.0027 (10)
C6	0.0264 (13)	0.0244 (11)	0.0306 (13)	−0.0075 (9)	−0.0024 (10)	0.0011 (9)
C7	0.0547 (19)	0.0535 (17)	0.0378 (16)	−0.0360 (15)	−0.0109 (14)	0.0127 (13)
C8	0.070 (2)	0.0589 (19)	0.0415 (17)	−0.0446 (17)	−0.0103 (16)	0.0164 (14)
C9	0.0384 (15)	0.0304 (13)	0.0401 (15)	−0.0135 (11)	−0.0029 (12)	0.0108 (11)
C10	0.062 (2)	0.057 (2)	0.060 (2)	−0.0307 (17)	−0.0116 (18)	0.0045 (16)
C11	0.062 (2)	0.0476 (19)	0.106 (3)	−0.0207 (17)	−0.034 (2)	0.035 (2)
C12	0.0282 (13)	0.0230 (10)	0.0224 (11)	−0.0070 (9)	−0.0020 (10)	0.0008 (9)
C13	0.0328 (14)	0.0227 (11)	0.0307 (13)	−0.0074 (10)	−0.0035 (11)	0.0042 (9)
C14	0.0311 (13)	0.0215 (11)	0.0333 (13)	−0.0061 (9)	−0.0006 (11)	−0.0008 (9)
C15	0.0281 (13)	0.0278 (11)	0.0254 (12)	−0.0104 (9)	−0.0037 (10)	−0.0013 (9)
C16	0.0361 (14)	0.0250 (11)	0.0309 (13)	−0.0116 (10)	−0.0007 (11)	0.0043 (10)
C17	0.0336 (14)	0.0220 (11)	0.0298 (13)	−0.0058 (9)	−0.0009 (11)	0.0017 (9)
C18	0.0295 (14)	0.0289 (12)	0.0380 (15)	−0.0071 (10)	−0.0007 (11)	−0.0054 (10)
C19	0.0309 (14)	0.0423 (14)	0.0382 (15)	−0.0132 (11)	0.0042 (12)	−0.0093 (12)
C20	0.0346 (14)	0.0275 (12)	0.0257 (12)	−0.0080 (10)	0.0037 (11)	−0.0012 (9)
C21	0.0446 (17)	0.0352 (14)	0.0438 (16)	−0.0140 (12)	0.0062 (13)	−0.0100 (12)
C22	0.0365 (17)	0.065 (2)	0.0524 (19)	−0.0132 (15)	0.0009 (15)	−0.0208 (16)

Pb1—S2	2.6999 (7)	C9—C10	1.480 (4)
Pb1—S3	2.7128 (6)	C9—C11	1.502 (4)
Pb1—S1	2.8877 (7)	C9—H9	1.0000
Pb1—S4	2.9472 (7)	C10—H10A	0.9800
S1—P1	1.9959 (9)	C10—H10B	0.9800
S2—P1	2.0115 (9)	C10—H10C	0.9800
S3—P2	2.0245 (9)	C11—H11A	0.9800
S4—P2	1.9877 (8)	C11—H11B	0.9800
P1—O2	1.5877 (17)	C11—H11C	0.9800
P1—C1	1.794 (2)	C12—C13	1.380 (3)
P2—O4	1.5848 (16)	C12—C17	1.400 (3)
P2—C12	1.797 (2)	C13—C14	1.381 (3)
O1—C4	1.356 (3)	C13—H13	0.9500
O1—C7	1.441 (3)	C14—C15	1.386 (3)
O2—C9	1.476 (3)	C14—H14	0.9500
O3—C15	1.363 (3)	C15—C16	1.392 (3)
O3—C18	1.437 (3)	C16—C17	1.379 (3)
O4—C20	1.471 (3)	C16—H16	0.9500
C1—C2	1.394 (3)	C17—H17	0.9500
C1—C6	1.399 (3)	C18—C19	1.500 (4)
C2—C3	1.384 (3)	C18—H18A	0.9900
C2—H2	0.9500	C18—H18B	0.9900
C3—C4	1.392 (3)	C19—H19A	0.9800
C3—H3	0.9500	C19—H19B	0.9800
C4—C5	1.398 (3)	C19—H19C	0.9800
C5—C6	1.382 (3)	C20—C22	1.503 (4)
C5—H5	0.9500	C20—C21	1.507 (3)
C6—H6	0.9500	C20—H20	1.0000
C7—C8	1.495 (4)	C21—H21A	0.9800
C7—H7A	0.9900	C21—H21B	0.9800
C7—H7B	0.9900	C21—H21C	0.9800
C8—H8A	0.9800	C22—H22A	0.9800
C8—H8B	0.9800	C22—H22B	0.9800
C8—H8C	0.9800	C22—H22C	0.9800
S2—Pb1—S3	93.09 (2)	C11—C9—H9	109.0
S2—Pb1—S1	72.692 (19)	C9—C10—H10A	109.5
S3—Pb1—S1	91.516 (19)	C9—C10—H10B	109.5
S2—Pb1—S4	82.708 (19)	H10A—C10—H10B	109.5
S3—Pb1—S4	71.841 (18)	C9—C10—H10C	109.5
S1—Pb1—S4	149.566 (17)	H10A—C10—H10C	109.5
P1—S1—Pb1	85.24 (3)	H10B—C10—H10C	109.5
P1—S2—Pb1	90.16 (3)	C9—C11—H11A	109.5
P2—S3—Pb1	90.51 (3)	C9—C11—H11B	109.5
P2—S4—Pb1	84.70 (3)	H11A—C11—H11B	109.5
O2—P1—C1	100.90 (10)	C9—C11—H11C	109.5
O2—P1—S1	110.94 (7)	H11A—C11—H11C	109.5
C1—P1—S1	111.88 (8)	H11B—C11—H11C	109.5
O2—P1—S2	111.34 (7)	C13—C12—C17	119.0 (2)
C1—P1—S2	109.69 (8)	C13—C12—P2	118.89 (18)
S1—P1—S2	111.63 (4)	C17—C12—P2	121.87 (17)
O4—P2—C12	101.33 (10)	C12—C13—C14	121.2 (2)
O4—P2—S4	112.17 (8)	C12—C13—H13	119.4
C12—P2—S4	111.43 (8)	C14—C13—H13	119.4
O4—P2—S3	109.88 (7)	C13—C14—C15	119.5 (2)
C12—P2—S3	109.56 (9)	C13—C14—H14	120.2
S4—P2—S3	111.98 (4)	C15—C14—H14	120.2
C4—O1—C7	118.0 (2)	O3—C15—C14	123.9 (2)
C9—O2—P1	119.79 (15)	O3—C15—C16	116.0 (2)
C15—O3—C18	117.87 (18)	C14—C15—C16	120.1 (2)
C20—O4—P2	119.72 (14)	C17—C16—C15	119.9 (2)
C2—C1—C6	118.8 (2)	C17—C16—H16	120.0
C2—C1—P1	119.26 (18)	C15—C16—H16	120.0
C6—C1—P1	121.73 (18)	C16—C17—C12	120.2 (2)
C3—C2—C1	121.4 (2)	C16—C17—H17	119.9
C3—C2—H2	119.3	C12—C17—H17	119.9
C1—C2—H2	119.3	O3—C18—C19	108.0 (2)
C2—C3—C4	119.3 (2)	O3—C18—H18A	110.1
C2—C3—H3	120.4	C19—C18—H18A	110.1
C4—C3—H3	120.4	O3—C18—H18B	110.1
O1—C4—C3	124.3 (2)	C19—C18—H18B	110.1
O1—C4—C5	115.9 (2)	H18A—C18—H18B	108.4
C3—C4—C5	119.8 (2)	C18—C19—H19A	109.5
C6—C5—C4	120.5 (2)	C18—C19—H19B	109.5
C6—C5—H5	119.8	H19A—C19—H19B	109.5
C4—C5—H5	119.8	C18—C19—H19C	109.5
C5—C6—C1	120.1 (2)	H19A—C19—H19C	109.5
C5—C6—H6	119.9	H19B—C19—H19C	109.5
C1—C6—H6	119.9	O4—C20—C22	107.2 (2)
O1—C7—C8	107.2 (2)	O4—C20—C21	107.8 (2)
O1—C7—H7A	110.3	C22—C20—C21	112.9 (2)
C8—C7—H7A	110.3	O4—C20—H20	109.6
O1—C7—H7B	110.3	C22—C20—H20	109.6
C8—C7—H7B	110.3	C21—C20—H20	109.6
H7A—C7—H7B	108.5	C20—C21—H21A	109.5
C7—C8—H8A	109.5	C20—C21—H21B	109.5
C7—C8—H8B	109.5	H21A—C21—H21B	109.5
H8A—C8—H8B	109.5	C20—C21—H21C	109.5
C7—C8—H8C	109.5	H21A—C21—H21C	109.5
H8A—C8—H8C	109.5	H21B—C21—H21C	109.5
H8B—C8—H8C	109.5	C20—C22—H22A	109.5
O2—C9—C10	108.7 (2)	C20—C22—H22B	109.5
O2—C9—C11	106.4 (2)	H22A—C22—H22B	109.5
C10—C9—C11	114.4 (3)	C20—C22—H22C	109.5
O2—C9—H9	109.0	H22A—C22—H22C	109.5
C10—C9—H9	109.0	H22B—C22—H22C	109.5
S2—Pb1—S1—P1	−3.39 (3)	C6—C1—C2—C3	0.0 (3)
S3—Pb1—S1—P1	−96.16 (3)	P1—C1—C2—C3	−175.01 (18)
S4—Pb1—S1—P1	−40.94 (5)	C1—C2—C3—C4	−1.2 (4)
S3—Pb1—S2—P1	93.98 (3)	C7—O1—C4—C3	−0.1 (4)
S1—Pb1—S2—P1	3.36 (3)	C7—O1—C4—C5	179.5 (2)
S4—Pb1—S2—P1	165.23 (3)	C2—C3—C4—O1	−179.1 (2)
S2—Pb1—S3—P2	87.41 (3)	C2—C3—C4—C5	1.3 (4)
S1—Pb1—S3—P2	160.16 (3)	O1—C4—C5—C6	−179.9 (2)
S4—Pb1—S3—P2	6.13 (3)	C3—C4—C5—C6	−0.2 (4)
S2—Pb1—S4—P2	−101.96 (3)	C4—C5—C6—C1	−0.9 (4)
S3—Pb1—S4—P2	−6.27 (3)	C2—C1—C6—C5	1.0 (3)
S1—Pb1—S4—P2	−66.05 (4)	P1—C1—C6—C5	175.93 (18)
Pb1—S1—P1—O2	129.49 (7)	C4—O1—C7—C8	−179.2 (2)
Pb1—S1—P1—C1	−118.68 (9)	P1—O2—C9—C10	117.6 (2)
Pb1—S1—P1—S2	4.68 (3)	P1—O2—C9—C11	−118.6 (2)
Pb1—S2—P1—O2	−129.58 (7)	O4—P2—C12—C13	160.0 (2)
Pb1—S2—P1—C1	119.60 (8)	S4—P2—C12—C13	40.5 (2)
Pb1—S2—P1—S1	−4.99 (4)	S3—P2—C12—C13	−84.0 (2)
Pb1—S4—P2—O4	132.71 (7)	O4—P2—C12—C17	−25.8 (2)
Pb1—S4—P2—C12	−114.48 (9)	S4—P2—C12—C17	−145.23 (19)
Pb1—S4—P2—S3	8.62 (4)	S3—P2—C12—C17	90.3 (2)
Pb1—S3—P2—O4	−134.69 (7)	C17—C12—C13—C14	1.4 (4)
Pb1—S3—P2—C12	114.82 (8)	P2—C12—C13—C14	175.8 (2)
Pb1—S3—P2—S4	−9.33 (4)	C12—C13—C14—C15	−1.1 (4)
C1—P1—O2—C9	−172.27 (18)	C18—O3—C15—C14	2.8 (3)
S1—P1—O2—C9	−53.57 (19)	C18—O3—C15—C16	−176.9 (2)
S2—P1—O2—C9	71.40 (18)	C13—C14—C15—O3	−179.5 (2)
C12—P2—O4—C20	−174.11 (17)	C13—C14—C15—C16	0.2 (4)
S4—P2—O4—C20	−55.17 (18)	O3—C15—C16—C17	−179.9 (2)
S3—P2—O4—C20	70.07 (17)	C14—C15—C16—C17	0.4 (4)
O2—P1—C1—C2	−145.78 (18)	C15—C16—C17—C12	0.0 (4)
S1—P1—C1—C2	96.21 (19)	C13—C12—C17—C16	−0.8 (4)
S2—P1—C1—C2	−28.2 (2)	P2—C12—C17—C16	−175.1 (2)
O2—P1—C1—C6	39.3 (2)	C15—O3—C18—C19	−178.9 (2)
S1—P1—C1—C6	−78.67 (19)	P2—O4—C20—C22	119.9 (2)
S2—P1—C1—C6	156.88 (17)	P2—O4—C20—C21	−118.3 (2)