A diisopropoxyphospho­nate monosulfone

The title compound, diisopropyl (diiso­propoxy­phosphoryl­methyl­sulfonyl­meth­yl)phosphonate, C₁₄H₃₂O₈P₂S, is a monosulfone of a diphosphate ester that has been investigated as a target for chemotherapy. The mol­ecule is in a quasi-gauche conformation with an approximate twofold axis. The S=O, P=O and P-O bonds average 1.444, 1.474 and 1.574 Å, respectively.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.095
• Data-to-parameter ratio = 25.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.18 Ratio

Author Response: ... This problem is caused by large thermal motion in an isopropyl group and could not be resolved by splitting the position.

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.47 Ratio

Author Response: ... This problem is due the H atoms associated with the above carbon atom.

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.390
           From the CIF: _refine_ls_abs_structure_Flack_su    0.070
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.14
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.51
           From the CIF: _reflns_number_total               6014
           Count of symmetry unique reflns         3330
           Completeness (_total/calc)            180.60%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2684
           Fraction of Friedel pairs measured     0.806
           Are heavy atom types Z>Si present        yes
PLAT033_ALERT_2_G Flack Parameter Value Deviates 2 * su from zero.       0.39
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

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

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S1. Comment

As part of our research into enzymes that are involved in the metastatic potential of tumor cells, a number of potential disulfone inhibitors for HIV-integrase have been identified (Meadows et al., 2005, Meadows & Gervay-Hague, 2006, Meadows et al., 2007). The monosulfone reagent reported here was envisioned and synthesized by a modification of the disulfone reaction (Hadd, et al., 2001).

Molecule (I), has an approximate twofold axis that passes through the central sulfur (Fig. 1). There are no short intermolecular contacts in the packing. As expected, the P=O distances are longer than the S=O distances. A quasi-gauche conformation is indicated by the torsion angles O=P—C—S (-41.65 (14)]° for O2—P1—C2—S1 and -41.75 (14)° for O6—P2—C3—S1) and two of the P—C—S=O angles (-41.92 (13)° for P1—C2—S1—O4 and -42.06 (13)° for P2—C3—S—O5). This conformation is in keeping with the result of a HF/6–31G** calculation on a similar molecule (Olivato, et al., 2001) that is the only other reported structure of a neutral sulfonylphosphonate in the Cambridge Structural Database (v. 5.28, Allen, 2002). The authors suggested that this conformation and the observed intramolecular P···O=S < S···O=P distances reflect a better electron- donating ability of the sulfonyl oxygen lone pair than the phosphoryl oxygen lone pair. In agreement with the previously reported structure, in (I) the P···O=S distances are 3.3094 (14) Å and 3.3082 (15) Å while the S···O=P distances are 3.1593 (16)Å and 3.1616 (15) Å.

Related literature

Theoretical and conformational studies on related molecules, together with the crystal structure of a sulfonylphosphonate, are reported by Olivato et al. (2001).

For related literature, see: Allen (2002); Hadd et al. (2001); Meadows & Gervay-Hague (2006); Meadows et al. (2005, 2007).

S2. Experimental

In the synthesis of (diisopropoxy-phosphorylmethanesulfonylmethyl)-phosphonic acid diisopropyl ester (I), to commercially available diisopropyl bromomethylphosphonate (Lancaster) (5.3 g, 20 mmol) in 15 ml of DMF were added potassium thioacetate (3.7 g, 30 mmol) and tetrabutylammonium iodide (370 mg) in sequence. The reaction mixture was heated to 358 K and stirred for 2 h. The solution was cooled and partitioned between water and ethyl acetate. The ethyl acetate layer was collected and dried over sodium sulfate and then evaporated to dryness. To the crude oil was added acetonitrile (15 ml), 3 M NaOH (7.4 ml) and methanol (7.4 ml) and the solution was stirred for 30 min. After 30 min, an additional 1 equiv of diisopropyl bromomethylphosphonate (4.5 g) was added to the mixture at room temperature and stirred overnight. The reaction mixture was then partitioned between water and ethyl acetate. The ethyl acetate layer was collected, dried over sodium sulfate, and evaporated to dryness. The crude oil was oxidized using oxone (24.9 g, 40 mmol) in methanol/water (ca 100 ml, 1:1) overnight to give a crude solid after diethyl ether/bicarbonate extraction. Recrystallization from diethyl ether/ hexane (1:1) provided 4.98 g of compound (I) as colorless, needle-like crystals (80% yield).

S3. Refinement

The methyl H atoms were constrained to an ideal geometry with C—H distances of 0.98 \%A and Uĩso~(H) = 1.5U~eq~(C), and each group was allowed to rotate freely about its C—C bond. Other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range 0.99–1.00 \%A and Uĩso~(H) = 1.2U~eq~(C). The refined value of the Flack parameter (0.37 (7)) indicated a degree of inversion twinning.

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. A view of (I). Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms have been omitted for clarity.

diisopropyl (diisopropoxyphosphorylmethylsulfonylmethyl)phosphonate

Crystal data

C14H32O8P2S	Dx = 1.312 Mg m^−3
Mr = 422.40	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 994 reflections
a = 9.8124 (9) Å	θ = 2.3–20.0°
b = 8.3298 (8) Å	µ = 0.34 mm^−1
c = 26.160 (3) Å	T = 90 K
V = 2138.2 (4) Å^3	Needle, colorless
Z = 4	0.47 × 0.13 × 0.08 mm
F(000) = 904

Data collection

Bruker SMART 1000 diffractometer	6014 independent reflections
Radiation source: fine-focus sealed tube	5398 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 8.3 pixels mm^-1	θmax = 30.5°, θmin = 1.6°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2005)	k = −11→11
Tmin = 0.858, Tmax = 0.974	l = −36→31
20017 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 0.3326P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
6014 reflections	Δρmax = 0.50 e Å^−3
235 parameters	Δρmin = −0.24 e Å^−3
1 restraint	Absolute structure: Flack (1983), 2547 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.39 (7)

Special details

Experimental. ¹H (400 MHz, CDCl₃) δ 4.83 (m, 1H), 4.09 (d, J=16 Hz, 1H), 1.37 (q, 6H). ¹³C (100 MHz, CDCl₃) δ 72.89 (d, J=6 Hz), 51.46 (d, J= 137 Hz), 24.29, J=4 Hz), 23.89 (d, J=5 Hz). LRMS (ESI) m/z calcd for C₁₄H₃₂O₈P₂S (M + H)⁺ is 423.13 and for (M + Na)⁺ is 445.13, found (M + H)⁺ 423.00 and (M + Na)+ 445.13. Anal. Calcd for C₁₄H₃₂O₈P₂S: C, 39.81; H, 7.64. Found: C, 39.88; H, 7.

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.88344 (5)	0.34367 (4)	0.84454 (2)	0.01515 (8)
P1	0.89600 (5)	0.11641 (6)	0.933576 (18)	0.01557 (10)
P2	0.87014 (4)	0.11416 (6)	0.756060 (18)	0.01532 (10)
O1	0.80358 (14)	−0.01724 (16)	0.95810 (6)	0.0205 (3)
O2	1.02766 (13)	0.05791 (16)	0.91381 (6)	0.0192 (3)
O3	0.90314 (15)	0.24746 (18)	0.97675 (7)	0.0195 (3)
O4	0.98063 (14)	0.43243 (17)	0.87483 (6)	0.0205 (3)
O5	0.78672 (14)	0.43246 (16)	0.81398 (6)	0.0199 (3)
O6	0.73851 (13)	0.05654 (16)	0.77615 (6)	0.0190 (3)
O7	0.96206 (14)	−0.02005 (16)	0.73148 (6)	0.0201 (3)
O8	0.86268 (14)	0.24438 (17)	0.71228 (7)	0.0201 (4)
C1	1.0218 (3)	0.2557 (3)	1.01095 (12)	0.0353 (7)
H1	1.1065	0.2353	0.9907	0.042*
C2	0.79050 (17)	0.2140 (2)	0.88622 (8)	0.0166 (3)
H2A	0.7442	0.1309	0.8655	0.020*
H2B	0.7193	0.2773	0.9039	0.020*
C3	0.97566 (17)	0.2129 (2)	0.80333 (7)	0.0159 (3)
H3A	1.0217	0.1302	0.8243	0.019*
H3B	1.0471	0.2755	0.7855	0.019*
C4	1.0252 (3)	0.4245 (4)	1.03118 (14)	0.0535 (9)
H4A	0.9419	0.4455	1.0508	0.080*
H4B	1.0309	0.5001	1.0026	0.080*
H4C	1.1048	0.4380	1.0534	0.080*
C5	1.0094 (5)	0.1308 (5)	1.05165 (14)	0.0823 (15)
H5A	1.0128	0.0239	1.0361	0.123*
H5B	0.9225	0.1443	1.0696	0.123*
H5C	1.0847	0.1423	1.0760	0.123*
C6	0.8124 (2)	−0.1874 (2)	0.94238 (8)	0.0228 (4)
H6	0.9097	−0.2167	0.9358	0.027*
C7	0.7587 (3)	−0.2831 (4)	0.98725 (11)	0.0453 (7)
H7A	0.6638	−0.2529	0.9939	0.068*
H7B	0.8141	−0.2604	1.0176	0.068*
H7C	0.7635	−0.3980	0.9793	0.068*
C8	0.7292 (2)	−0.2133 (3)	0.89447 (9)	0.0260 (4)
H8A	0.7708	−0.1546	0.8660	0.039*
H8B	0.6362	−0.1740	0.9000	0.039*
H8C	0.7266	−0.3281	0.8864	0.039*
C9	0.9539 (2)	−0.1899 (2)	0.74786 (8)	0.0217 (4)
H9	0.8568	−0.2196	0.7545	0.026*
C10	1.0364 (2)	−0.2130 (3)	0.79563 (9)	0.0245 (4)
H10A	0.9948	−0.1524	0.8237	0.037*
H10B	1.1295	−0.1745	0.7899	0.037*
H10C	1.0386	−0.3273	0.8045	0.037*
C11	1.0085 (3)	−0.2872 (4)	0.70366 (10)	0.0430 (7)
H11A	1.1050	−0.2616	0.6984	0.064*
H11B	0.9570	−0.2613	0.6726	0.064*
H11C	0.9989	−0.4018	0.7113	0.064*
C12	0.7431 (2)	0.2542 (3)	0.67915 (11)	0.0321 (6)
H12	0.6593	0.2357	0.7001	0.039*
C13	0.7408 (3)	0.4223 (4)	0.65881 (13)	0.0499 (8)
H13A	0.8210	0.4400	0.6372	0.075*
H13B	0.7418	0.4984	0.6874	0.075*
H13C	0.6580	0.4384	0.6385	0.075*
C14	0.7511 (5)	0.1291 (4)	0.63869 (15)	0.0702 (11)
H14A	0.7596	0.0231	0.6546	0.105*
H14B	0.8307	0.1493	0.6170	0.105*
H14C	0.6683	0.1324	0.6178	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01363 (16)	0.01357 (15)	0.01826 (17)	0.00011 (15)	−0.00119 (14)	0.0008 (2)
P1	0.0158 (2)	0.0165 (2)	0.0145 (2)	−0.00028 (15)	−0.00081 (17)	−0.0002 (2)
P2	0.0149 (2)	0.0155 (2)	0.0155 (2)	0.00026 (15)	−0.00078 (16)	0.0012 (2)
O1	0.0239 (7)	0.0181 (6)	0.0196 (7)	−0.0029 (5)	0.0008 (5)	0.0016 (6)
O2	0.0178 (6)	0.0198 (6)	0.0200 (7)	0.0023 (5)	−0.0006 (5)	−0.0001 (5)
O3	0.0218 (7)	0.0205 (9)	0.0162 (9)	−0.0012 (5)	−0.0019 (6)	−0.0039 (5)
O4	0.0186 (6)	0.0177 (6)	0.0253 (8)	−0.0032 (5)	−0.0019 (5)	−0.0031 (6)
O5	0.0184 (6)	0.0170 (6)	0.0241 (8)	0.0036 (5)	−0.0023 (5)	0.0037 (6)
O6	0.0181 (6)	0.0200 (6)	0.0191 (7)	−0.0016 (5)	−0.0009 (5)	0.0003 (5)
O7	0.0219 (7)	0.0165 (6)	0.0218 (7)	0.0024 (5)	0.0024 (5)	0.0006 (5)
O8	0.0200 (7)	0.0215 (9)	0.0189 (10)	−0.0004 (5)	−0.0019 (5)	0.0043 (5)
C1	0.0282 (11)	0.0524 (18)	0.0253 (15)	0.0067 (10)	−0.0087 (9)	−0.0158 (11)
C2	0.0129 (7)	0.0175 (8)	0.0196 (10)	0.0009 (6)	−0.0003 (6)	0.0007 (7)
C3	0.0130 (7)	0.0180 (7)	0.0167 (9)	0.0001 (6)	−0.0006 (6)	0.0008 (7)
C4	0.0459 (16)	0.061 (2)	0.053 (2)	−0.0150 (14)	−0.0063 (14)	−0.0313 (17)
C5	0.141 (4)	0.069 (3)	0.037 (2)	0.023 (3)	−0.043 (2)	0.0053 (17)
C6	0.0265 (9)	0.0161 (9)	0.0259 (11)	0.0002 (7)	−0.0040 (7)	0.0022 (7)
C7	0.075 (2)	0.0267 (12)	0.0344 (16)	−0.0088 (13)	−0.0016 (14)	0.0128 (12)
C8	0.0320 (10)	0.0199 (9)	0.0261 (12)	−0.0022 (8)	−0.0045 (8)	−0.0003 (9)
C9	0.0235 (9)	0.0156 (8)	0.0260 (11)	−0.0011 (6)	−0.0029 (7)	0.0001 (7)
C10	0.0288 (10)	0.0184 (9)	0.0262 (12)	0.0001 (8)	−0.0046 (8)	0.0029 (9)
C11	0.075 (2)	0.0239 (11)	0.0304 (16)	0.0092 (12)	−0.0089 (13)	−0.0082 (11)
C12	0.0284 (11)	0.0445 (16)	0.0234 (15)	−0.0037 (9)	−0.0100 (9)	0.0141 (10)
C13	0.0465 (16)	0.0557 (19)	0.0474 (19)	0.0145 (13)	−0.0021 (13)	0.0302 (15)
C14	0.108 (3)	0.062 (2)	0.041 (2)	−0.023 (2)	−0.033 (2)	0.0001 (17)

Geometric parameters (Å, º)

S1—O4	1.4435 (15)	C5—H5C	0.9800
S1—O5	1.4446 (14)	C6—C8	1.511 (3)
S1—C3	1.780 (2)	C6—C7	1.514 (3)
S1—C2	1.785 (2)	C6—H6	1.0000
P1—O2	1.4744 (14)	C7—H7A	0.9800
P1—O3	1.5722 (17)	C7—H7B	0.9800
P1—O1	1.5727 (14)	C7—H7C	0.9800
P1—C2	1.808 (2)	C8—H8A	0.9800
P2—O6	1.4747 (14)	C8—H8B	0.9800
P2—O7	1.5737 (14)	C8—H8C	0.9800
P2—O8	1.5791 (18)	C9—C10	1.501 (3)
P2—C3	1.811 (2)	C9—C11	1.510 (3)
O1—C6	1.478 (2)	C9—H9	1.0000
O3—C1	1.470 (3)	C10—H10A	0.9800
O7—C9	1.480 (2)	C10—H10B	0.9800
O8—C12	1.461 (3)	C10—H10C	0.9800
C1—C5	1.493 (5)	C11—H11A	0.9800
C1—C4	1.503 (4)	C11—H11B	0.9800
C1—H1	1.0000	C11—H11C	0.9800
C2—H2A	0.9900	C12—C14	1.487 (5)
C2—H2B	0.9900	C12—C13	1.498 (4)
C3—H3A	0.9900	C12—H12	1.0000
C3—H3B	0.9900	C13—H13A	0.9800
C4—H4A	0.9800	C13—H13B	0.9800
C4—H4B	0.9800	C13—H13C	0.9800
C4—H4C	0.9800	C14—H14A	0.9800
C5—H5A	0.9800	C14—H14B	0.9800
C5—H5B	0.9800	C14—H14C	0.9800
O4—S1—O5	118.40 (7)	O1—C6—C7	105.61 (19)
O4—S1—C3	108.06 (8)	C8—C6—C7	112.32 (19)
O5—S1—C3	108.18 (9)	O1—C6—H6	109.7
O4—S1—C2	108.19 (9)	C8—C6—H6	109.7
O5—S1—C2	108.19 (9)	C7—C6—H6	109.7
C3—S1—C2	105.04 (7)	C6—C7—H7A	109.5
O2—P1—O3	116.25 (8)	C6—C7—H7B	109.5
O2—P1—O1	114.48 (8)	H7A—C7—H7B	109.5
O3—P1—O1	102.95 (9)	C6—C7—H7C	109.5
O2—P1—C2	114.21 (9)	H7A—C7—H7C	109.5
O3—P1—C2	101.86 (9)	H7B—C7—H7C	109.5
O1—P1—C2	105.53 (8)	C6—C8—H8A	109.5
O6—P2—O7	114.61 (8)	C6—C8—H8B	109.5
O6—P2—O8	116.19 (8)	H8A—C8—H8B	109.5
O7—P2—O8	102.60 (9)	C6—C8—H8C	109.5
O6—P2—C3	113.92 (9)	H8A—C8—H8C	109.5
O7—P2—C3	105.91 (8)	H8B—C8—H8C	109.5
O8—P2—C3	102.10 (9)	O7—C9—C10	109.55 (16)
C6—O1—P1	122.11 (13)	O7—C9—C11	105.78 (18)
C1—O3—P1	120.32 (15)	C10—C9—C11	112.18 (19)
C9—O7—P2	121.98 (13)	O7—C9—H9	109.8
C12—O8—P2	120.39 (14)	C10—C9—H9	109.8
O3—C1—C5	109.7 (3)	C11—C9—H9	109.8
O3—C1—C4	106.0 (2)	C9—C10—H10A	109.5
C5—C1—C4	113.7 (3)	C9—C10—H10B	109.5
O3—C1—H1	109.1	H10A—C10—H10B	109.5
C5—C1—H1	109.1	C9—C10—H10C	109.5
C4—C1—H1	109.1	H10A—C10—H10C	109.5
S1—C2—P1	113.46 (9)	H10B—C10—H10C	109.5
S1—C2—H2A	108.9	C9—C11—H11A	109.5
P1—C2—H2A	108.9	C9—C11—H11B	109.5
S1—C2—H2B	108.9	H11A—C11—H11B	109.5
P1—C2—H2B	108.9	C9—C11—H11C	109.5
H2A—C2—H2B	107.7	H11A—C11—H11C	109.5
S1—C3—P2	113.65 (9)	H11B—C11—H11C	109.5
S1—C3—H3A	108.8	O8—C12—C14	109.9 (2)
P2—C3—H3A	108.8	O8—C12—C13	106.0 (2)
S1—C3—H3B	108.8	C14—C12—C13	113.7 (3)
P2—C3—H3B	108.8	O8—C12—H12	109.0
H3A—C3—H3B	107.7	C14—C12—H12	109.0
C1—C4—H4A	109.5	C13—C12—H12	109.0
C1—C4—H4B	109.5	C12—C13—H13A	109.5
H4A—C4—H4B	109.5	C12—C13—H13B	109.5
C1—C4—H4C	109.5	H13A—C13—H13B	109.5
H4A—C4—H4C	109.5	C12—C13—H13C	109.5
H4B—C4—H4C	109.5	H13A—C13—H13C	109.5
C1—C5—H5A	109.5	H13B—C13—H13C	109.5
C1—C5—H5B	109.5	C12—C14—H14A	109.5
H5A—C5—H5B	109.5	C12—C14—H14B	109.5
C1—C5—H5C	109.5	H14A—C14—H14B	109.5
H5A—C5—H5C	109.5	C12—C14—H14C	109.5
H5B—C5—H5C	109.5	H14A—C14—H14C	109.5
O1—C6—C8	109.63 (16)	H14B—C14—H14C	109.5
O2—P1—O1—C6	−27.16 (17)	C3—S1—C2—P1	73.30 (14)
O3—P1—O1—C6	−154.28 (14)	O2—P1—C2—S1	−41.65 (14)
C2—P1—O1—C6	99.30 (15)	O3—P1—C2—S1	84.50 (12)
O2—P1—O3—C1	−27.2 (2)	O1—P1—C2—S1	−168.27 (10)
O1—P1—O3—C1	98.8 (2)	O4—S1—C3—P2	−171.38 (10)
C2—P1—O3—C1	−152.02 (19)	O5—S1—C3—P2	−42.06 (13)
O6—P2—O7—C9	−27.84 (17)	C2—S1—C3—P2	73.30 (13)
O8—P2—O7—C9	−154.70 (14)	O6—P2—C3—S1	−41.75 (14)
C3—P2—O7—C9	98.62 (15)	O7—P2—C3—S1	−168.63 (10)
O6—P2—O8—C12	−25.8 (2)	O8—P2—C3—S1	84.33 (12)
O7—P2—O8—C12	100.08 (19)	P1—O1—C6—C8	−82.50 (19)
C3—P2—O8—C12	−150.33 (19)	P1—O1—C6—C7	156.28 (17)
P1—O3—C1—C5	−79.7 (3)	P2—O7—C9—C10	−81.56 (19)
P1—O3—C1—C4	157.1 (2)	P2—O7—C9—C11	157.34 (16)
O4—S1—C2—P1	−41.92 (13)	P2—O8—C12—C14	−80.1 (3)
O5—S1—C2—P1	−171.33 (10)	P2—O8—C12—C13	156.62 (19)