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The title mol­ecule, diisopropyl (diisopropoxy­phosphoryl­methyl­sulfonyl­methyl­sulfonyl­meth­yl)phospho­nate, C15H34O10P2S2, represents a disulfone of a phosphate ester that has been investigated as a target for chemotherapy. The disulfone has four half-mol­ecules with crystallographic twofold symmetry in the asymmetric unit. The S=O, P=O and P-O bonds average 1.439, 1.472 and 1.567 Å, respectively. Three isopropyl groups are each disordered over two sites, two of them in a 2:1 ratio and the other in a 3:2 ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702507X/pk2026sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680702507X/pk2026Isup2.hkl
Contains datablock I

CCDC reference: 651535

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.041
  • wR factor = 0.117
  • Data-to-parameter ratio = 22.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.00 Ratio
Author Response: Disorder in the isopropyl groups gives rise to some large anisotropic thermal parameters.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.23 Ratio
Author Response: This is correlated to the above.

Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.95 Ratio
Author Response: Disorder in the isopropyl groups gives rise to some large anisotropic thermal parameters.
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.00 Ratio
Author Response: This is correlated to the above.
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H7A    ..  H14F    ..       1.93 Ang.

Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group P2/c .... P2/n PLAT213_ALERT_2_C Atom C15B has ADP max/min Ratio ............. 3.10 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.04 Ratio
Author Response: Disorder in the isopropyl groups gives rise to some large anisotropic thermal parameters.
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.77 Ratio
Author Response: This is correlated to the above.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C3A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C3B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C13A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C13B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C36B
PLAT301_ALERT_3_C Main Residue  Disorder .........................      13.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of P1 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of P11 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of P31 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 9
2 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Organophosphates are ubiquitous in nature as substrates for key enzymes including glycosyltransferases, RNA/DNA polymerases, HIV-1 integrase and kinases. Inhibitors of these enzymes have proven useful as probes for biomechanistic elucidation and represent important targets for chemotherapeutic intervention. In continuation of the synthesis of enzyme substrate analogs and screening of compounds for inhibition against relevant enzymes, the disulfone reagent (I) has been developed and extensively used in the Gervay-Hague laboratories (Hadd et al., 2001, Meadows et al., 2005, Meadows & Gervay-Hague, 2006, Meadows et al., 2007).

Disulfone (I), has Z'=2; however, there are four half-molecules in the asymmetric unit. A crystallographic twofold axis passes through the central carbon atom in each of the four molecules in the structure (Fig. 1). The differences among the molecules are slight, as can be seen by their common orientations in the figure. Three of the four have varying degrees of disorder in one of the isopropyl groups. There are only minor conformational differences in the isopropyl groups that distinguish one molecule from another. Values of the individual bonds show good internal consistency and also agree with those of the mono-sulfone (Wong et al., 2007). The average S=O, P=O, and P—O distances, together with their average deviations in square brackets are 1.439[3] Å, 1.472[1] Å, and 1.567[2] Å, respectively. There are no short intermolecular interactions. The phosphoryl and sulfonyl intramolecular interactions follow the trend P···O=S < S···O=S < S···O=P with average values and average deviations in square brackets of 3.209[24] Å < 3.270[6] Å < 3.330[12] Å, respectively. These values compare well with those described by Olivato et al. (2001). The P—C—S—C backbone has average torsion angles of -71.9[17]° whereas that of the C—S—C—S backbone is -68.1[5]°.

Related literature top

Theoretical and conformational studies on related molecules, together with the crystal structure of a sulfonylphosphonate, are reported by Olivato et al. (2001). Studies related to chemotherapeutic uses of disulfones are reported by Meadows et al. (2005, 2007) and Meadows & Gervay-Hague (2006).

For related literature, see: Hadd et al. (2001); Wong et al. (2007).

Experimental top

The synthesis of (I) was reported earlier (Hadd et al., 2001). Crystals were grown from diethyl ether.

Refinement top

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 structure was refined as a pseudomerohedral twin, twin law (0 0 - 1 0 - 1 0 - 1 0 0) and twin parameter 0.1098 (6). Three isopropyl groups suffer rotational disorder and were modeled with split positions. The occupancies were fixed in the final cycles of refinement.

Structure description top

Organophosphates are ubiquitous in nature as substrates for key enzymes including glycosyltransferases, RNA/DNA polymerases, HIV-1 integrase and kinases. Inhibitors of these enzymes have proven useful as probes for biomechanistic elucidation and represent important targets for chemotherapeutic intervention. In continuation of the synthesis of enzyme substrate analogs and screening of compounds for inhibition against relevant enzymes, the disulfone reagent (I) has been developed and extensively used in the Gervay-Hague laboratories (Hadd et al., 2001, Meadows et al., 2005, Meadows & Gervay-Hague, 2006, Meadows et al., 2007).

Disulfone (I), has Z'=2; however, there are four half-molecules in the asymmetric unit. A crystallographic twofold axis passes through the central carbon atom in each of the four molecules in the structure (Fig. 1). The differences among the molecules are slight, as can be seen by their common orientations in the figure. Three of the four have varying degrees of disorder in one of the isopropyl groups. There are only minor conformational differences in the isopropyl groups that distinguish one molecule from another. Values of the individual bonds show good internal consistency and also agree with those of the mono-sulfone (Wong et al., 2007). The average S=O, P=O, and P—O distances, together with their average deviations in square brackets are 1.439[3] Å, 1.472[1] Å, and 1.567[2] Å, respectively. There are no short intermolecular interactions. The phosphoryl and sulfonyl intramolecular interactions follow the trend P···O=S < S···O=S < S···O=P with average values and average deviations in square brackets of 3.209[24] Å < 3.270[6] Å < 3.330[12] Å, respectively. These values compare well with those described by Olivato et al. (2001). The P—C—S—C backbone has average torsion angles of -71.9[17]° whereas that of the C—S—C—S backbone is -68.1[5]°.

Theoretical and conformational studies on related molecules, together with the crystal structure of a sulfonylphosphonate, are reported by Olivato et al. (2001). Studies related to chemotherapeutic uses of disulfones are reported by Meadows et al. (2005, 2007) and Meadows & Gervay-Hague (2006).

For related literature, see: Hadd et al. (2001); Wong et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2005); 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 top
[Figure 1] Fig. 1. A view of the four molecules of (I) in a common orientation. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms have been omitted for clarity. Symmetry codes: i = 1/2 - x, y, 1/2 - z; ii = 1.5 - x, y, 1.5 - z; iii = 1/2 - x, y, 1.5 - z; iv = 1.5 - x, y, 1/2 - z.
[Figure 2] Fig. 2. A view of the four molecules of (I) projected along the b-direction.
diisopropyl (diisopropoxyphosphorylmethylsulfonylmethylsulfonylmethyl)phosphonate top
Crystal data top
C15H34O10P2S2F(000) = 2128
Mr = 500.50Dx = 1.373 Mg m3
Monoclinic, P2/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yacCell parameters from 7807 reflections
a = 21.7314 (17) Åθ = 2.9–30.5°
b = 10.2307 (8) ŵ = 0.40 mm1
c = 21.8150 (17) ÅT = 180 K
β = 92.922 (5)°Block, colorless
V = 4843.8 (7) Å30.40 × 0.25 × 0.13 mm
Z = 8
Data collection top
Bruker SMART APEX II
diffractometer
14085 independent reflections
Radiation source: fine-focus sealed tube12471 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 8.3 pixels mm-1θmax = 30.0°, θmin = 2.9°
ω and φ scansh = 3030
Absorption correction: multi-scan
(SADABS; Sheldrick, 2005)
k = 1414
Tmin = 0.857, Tmax = 0.950l = 3030
53365 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0753P)2 + 0.8408P]
where P = (Fo2 + 2Fc2)/3
14085 reflections(Δ/σ)max = 0.026
627 parametersΔρmax = 0.50 e Å3
9 restraintsΔρmin = 0.61 e Å3
Crystal data top
C15H34O10P2S2V = 4843.8 (7) Å3
Mr = 500.50Z = 8
Monoclinic, P2/nMo Kα radiation
a = 21.7314 (17) ŵ = 0.40 mm1
b = 10.2307 (8) ÅT = 180 K
c = 21.8150 (17) Å0.40 × 0.25 × 0.13 mm
β = 92.922 (5)°
Data collection top
Bruker SMART APEX II
diffractometer
14085 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2005)
12471 reflections with I > 2σ(I)
Tmin = 0.857, Tmax = 0.950Rint = 0.052
53365 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0419 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.08Δρmax = 0.50 e Å3
14085 reflectionsΔρmin = 0.61 e Å3
627 parameters
Special details top

Experimental. The data collection temperature of 180 K was used due to an apparent destructive phase transition as the temperature was further lowered to 90 K.

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*/UeqOcc. (<1)
P10.085776 (19)0.12874 (4)0.26172 (2)0.02586 (9)
S10.217544 (18)0.10297 (4)0.310518 (18)0.02721 (8)
O10.26109 (6)0.00310 (15)0.32980 (6)0.0377 (3)
O20.19921 (6)0.19881 (14)0.35408 (6)0.0404 (3)
O30.10166 (6)0.25460 (11)0.23388 (6)0.0317 (2)
O40.03976 (6)0.04176 (12)0.22177 (6)0.0337 (3)
O50.05649 (6)0.13298 (12)0.32571 (6)0.0333 (3)
C10.25000.1938 (2)0.25000.0256 (4)
H10.28160.24940.26800.031*
C20.15125 (7)0.02299 (15)0.27774 (8)0.0281 (3)
H2A0.13900.04680.30610.034*
H2B0.16230.01940.23900.034*
C3A0.0269 (2)0.0588 (4)0.1572 (2)0.0368 (9)0.57
H3A0.02640.15370.14610.044*0.57
C4A0.0772 (2)0.0128 (8)0.1250 (2)0.0779 (17)0.57
H4AA0.11660.03200.13330.117*0.57
H4AB0.06730.01370.08060.117*0.57
H4AC0.08020.10280.14020.117*0.57
C5A0.03493 (17)0.0028 (7)0.1420 (2)0.0652 (13)0.57
H5AA0.06680.04400.16350.098*0.57
H5AB0.03410.09450.15500.098*0.57
H5AC0.04420.00190.09760.098*0.57
C3B0.0476 (3)0.0236 (6)0.1535 (3)0.0359 (12)0.43
H3B0.09250.02820.14540.043*0.43
C4B0.0240 (3)0.1129 (5)0.1378 (3)0.0572 (14)0.43
H4BA0.02220.12490.09320.086*0.43
H4BB0.01740.12380.15310.086*0.43
H4BC0.05180.17800.15710.086*0.43
C5B0.0147 (4)0.1294 (6)0.1186 (3)0.0661 (17)0.43
H5BA0.03020.21440.13320.099*0.43
H5BB0.02950.12340.12490.099*0.43
H5BC0.02180.12010.07480.099*0.43
C60.01642 (8)0.24022 (18)0.34433 (9)0.0361 (4)
H60.03060.32410.32620.043*
C70.02495 (14)0.2464 (3)0.41301 (11)0.0635 (7)
H7A0.06900.25230.42480.095*
H7B0.00780.16740.43090.095*
H7C0.00370.32350.42810.095*
C80.04901 (10)0.2129 (3)0.32162 (13)0.0566 (6)
H8A0.05110.20820.27670.085*
H8B0.07590.28330.33490.085*
H8C0.06250.12960.33850.085*
P110.882618 (18)0.37244 (4)0.659619 (18)0.02439 (8)
S110.816104 (16)0.40065 (4)0.777057 (16)0.02385 (8)
O110.79536 (5)0.50171 (14)0.81719 (5)0.0351 (3)
O120.86010 (6)0.30603 (15)0.80066 (6)0.0393 (3)
O130.84913 (6)0.24861 (12)0.64917 (6)0.0325 (2)
O140.88947 (6)0.45678 (13)0.60039 (5)0.0353 (3)
O150.95002 (5)0.36449 (12)0.68835 (5)0.0300 (2)
C110.75000.3085 (2)0.75000.0229 (4)
H110.73790.25290.78270.027*
C120.84566 (7)0.47943 (15)0.71235 (7)0.0242 (3)
H12A0.87580.54650.72700.029*
H12B0.81140.52530.68980.029*
C13A0.8499 (4)0.4293 (5)0.5436 (3)0.0325 (10)0.68
H13A0.83150.34000.54590.039*0.68
C14A0.80000 (19)0.5314 (5)0.54370 (17)0.0664 (11)0.68
H14A0.77370.51540.57810.100*0.68
H14B0.77510.52700.50500.100*0.68
H14C0.81870.61820.54810.100*0.68
C15A0.8897 (3)0.4383 (7)0.4904 (3)0.0649 (17)0.68
H15A0.92330.37470.49530.097*0.68
H15B0.90690.52660.48820.097*0.68
H15C0.86520.41940.45250.097*0.68
C13B0.8467 (8)0.4713 (10)0.5464 (6)0.039 (3)0.32
H13B0.80650.42660.55270.047*0.32
C14B0.8369 (4)0.6099 (8)0.5236 (3)0.0562 (19)0.32
H14D0.81380.65930.55320.084*0.32
H14E0.81380.60840.48380.084*0.32
H14F0.87700.65170.51880.084*0.32
C15B0.8838 (9)0.3987 (11)0.5009 (5)0.090 (6)0.32
H15D0.89210.30980.51580.135*0.32
H15E0.92290.44430.49600.135*0.32
H15F0.86060.39480.46120.135*0.32
C160.99712 (8)0.28756 (18)0.65737 (8)0.0326 (3)
H160.97630.22460.62800.039*
C171.03399 (10)0.2135 (2)0.70582 (10)0.0456 (5)
H17A1.00620.16080.72980.068*
H17B1.05650.27520.73300.068*
H17C1.06330.15600.68630.068*
C181.03599 (10)0.3813 (2)0.62260 (12)0.0549 (6)
H18A1.01020.42510.59060.082*
H18B1.06900.33310.60360.082*
H18C1.05400.44680.65100.082*
P210.24751 (2)0.86489 (4)0.913720 (18)0.02752 (9)
S210.191320 (19)0.89188 (4)0.785262 (18)0.02933 (9)
O210.17004 (6)0.99185 (15)0.74286 (6)0.0377 (3)
O220.14858 (7)0.79628 (15)0.80573 (7)0.0458 (3)
O230.27713 (6)0.74223 (12)0.89584 (6)0.0339 (3)
O240.28696 (6)0.95280 (13)0.95945 (6)0.0374 (3)
O250.18443 (6)0.85339 (13)0.94472 (6)0.0352 (3)
C210.25000.8007 (2)0.75000.0289 (4)
H210.23050.74510.71940.035*
C220.22707 (8)0.97182 (16)0.84988 (7)0.0294 (3)
H22A0.19891.04020.86400.035*
H22B0.26481.01590.83700.035*
C230.35436 (10)0.95121 (19)0.96529 (9)0.0398 (4)
H230.37010.86580.95020.048*
C240.37912 (12)1.0610 (2)0.92810 (11)0.0542 (5)
H24A0.36791.04650.88450.081*
H24B0.42411.06410.93420.081*
H24C0.36151.14390.94130.081*
C250.37131 (14)0.9660 (3)1.03304 (10)0.0633 (7)
H25A0.35200.89581.05580.095*
H25B0.35681.05081.04740.095*
H25C0.41620.96091.03980.095*
C260.17096 (11)0.74753 (19)0.98726 (9)0.0448 (5)
H260.19110.66540.97370.054*
C270.10246 (14)0.7309 (3)0.98155 (14)0.0686 (8)
H27A0.08940.71780.93830.103*
H27B0.08250.80930.99710.103*
H27C0.09060.65481.00550.103*
C280.19542 (14)0.7815 (3)1.05117 (10)0.0619 (7)
H28A0.24040.78791.05180.093*
H28B0.18360.71331.07980.093*
H28C0.17820.86551.06340.093*
P310.84281 (2)0.63324 (4)0.119898 (18)0.02613 (9)
S310.722851 (17)0.60354 (4)0.184137 (17)0.02589 (8)
O310.68284 (5)0.50178 (14)0.20468 (5)0.0342 (2)
O320.69880 (6)0.69798 (14)0.14054 (6)0.0402 (3)
O330.85417 (6)0.75450 (12)0.15487 (6)0.0352 (3)
O340.90134 (5)0.54539 (12)0.11237 (6)0.0321 (2)
O350.81563 (6)0.64658 (14)0.05247 (6)0.0368 (3)
C310.75000.6947 (2)0.25000.0259 (4)
H310.71720.75030.26200.031*
C320.78787 (7)0.52589 (15)0.15428 (7)0.0258 (3)
H32A0.77310.46160.12300.031*
H32B0.80960.47670.18790.031*
C330.95852 (8)0.5560 (2)0.15169 (9)0.0383 (4)
H330.96110.64470.17090.046*
C340.95734 (11)0.4539 (2)0.20065 (11)0.0542 (6)
H34A0.92300.47110.22690.081*
H34B0.99620.45610.22550.081*
H34C0.95210.36760.18160.081*
C351.01006 (11)0.5392 (4)0.10867 (14)0.0830 (11)
H35A1.00740.60790.07730.125*
H35B1.00660.45340.08880.125*
H35C1.04980.54550.13190.125*
C36A0.8487 (5)0.7282 (12)0.0093 (4)0.060 (3)0.65
H36A0.88230.77840.03170.072*0.65
C37A0.8027 (2)0.8201 (5)0.0206 (3)0.0573 (12)0.65
H37A0.78510.87540.01070.086*0.65
H37B0.76970.76980.04190.086*0.65
H37C0.82310.87510.05020.086*0.65
C38A0.8750 (4)0.6385 (7)0.0356 (3)0.113 (3)0.65
H38A0.90530.58110.01440.169*0.65
H38B0.89520.68940.06690.169*0.65
H38C0.84200.58550.05520.169*0.65
C36B0.8490 (13)0.7087 (18)0.0041 (7)0.050 (4)0.35
H36B0.89390.69900.01560.060*0.35
C37B0.8369 (6)0.6380 (10)0.0574 (3)0.070 (3)0.35
H37D0.84330.54390.05160.105*0.35
H37E0.86530.67100.08730.105*0.35
H37F0.79440.65400.07260.105*0.35
C38B0.8366 (10)0.8457 (11)0.0001 (7)0.129 (8)0.35
H38D0.84640.88690.03980.193*0.35
H38E0.79300.85940.01190.193*0.35
H38F0.86210.88470.03110.193*0.35
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.02296 (18)0.02212 (17)0.0326 (2)0.00184 (13)0.00276 (14)0.00063 (14)
S10.02454 (18)0.03144 (19)0.02572 (18)0.00067 (14)0.00205 (13)0.00022 (13)
O10.0299 (6)0.0471 (7)0.0360 (6)0.0053 (5)0.0004 (5)0.0141 (6)
O20.0374 (7)0.0495 (8)0.0346 (6)0.0019 (6)0.0058 (5)0.0155 (6)
O30.0331 (6)0.0227 (5)0.0393 (6)0.0031 (4)0.0013 (5)0.0012 (4)
O40.0309 (6)0.0335 (6)0.0365 (6)0.0089 (5)0.0001 (5)0.0007 (5)
O50.0328 (6)0.0307 (6)0.0372 (6)0.0057 (5)0.0089 (5)0.0005 (5)
C10.0236 (9)0.0224 (9)0.0309 (10)0.0000.0013 (8)0.000
C20.0242 (7)0.0232 (7)0.0371 (8)0.0006 (5)0.0039 (6)0.0000 (6)
C3A0.048 (3)0.0241 (19)0.0377 (19)0.0003 (15)0.0046 (18)0.0018 (15)
C4A0.046 (2)0.147 (5)0.041 (2)0.012 (3)0.0058 (18)0.017 (3)
C5A0.0305 (17)0.111 (4)0.053 (2)0.006 (2)0.0097 (15)0.019 (3)
C3B0.046 (3)0.027 (3)0.035 (2)0.006 (2)0.003 (2)0.005 (2)
C4B0.077 (4)0.038 (2)0.055 (3)0.001 (2)0.011 (3)0.014 (2)
C5B0.100 (5)0.046 (3)0.050 (3)0.001 (3)0.014 (3)0.008 (2)
C60.0325 (8)0.0344 (8)0.0421 (9)0.0092 (7)0.0083 (7)0.0002 (7)
C70.0773 (18)0.0703 (16)0.0431 (12)0.0337 (14)0.0063 (11)0.0090 (11)
C80.0305 (10)0.0675 (15)0.0716 (16)0.0085 (10)0.0020 (9)0.0118 (12)
P110.02121 (18)0.02863 (19)0.02384 (18)0.00176 (14)0.00612 (13)0.00264 (13)
S110.01977 (16)0.03162 (18)0.02031 (16)0.00039 (13)0.00258 (12)0.00054 (12)
O110.0302 (6)0.0473 (7)0.0282 (6)0.0065 (5)0.0067 (4)0.0148 (5)
O120.0268 (6)0.0555 (8)0.0353 (6)0.0076 (6)0.0001 (5)0.0145 (6)
O130.0317 (6)0.0299 (6)0.0364 (6)0.0036 (5)0.0066 (5)0.0081 (5)
O140.0294 (6)0.0523 (8)0.0245 (5)0.0064 (5)0.0043 (4)0.0062 (5)
O150.0218 (5)0.0395 (6)0.0291 (6)0.0031 (4)0.0055 (4)0.0048 (5)
C110.0217 (9)0.0220 (9)0.0253 (9)0.0000.0058 (7)0.000
C120.0219 (6)0.0246 (6)0.0266 (7)0.0028 (5)0.0062 (5)0.0002 (5)
C13A0.0372 (17)0.035 (2)0.0257 (17)0.002 (2)0.0016 (12)0.0004 (18)
C14A0.064 (2)0.079 (3)0.054 (2)0.029 (2)0.0243 (17)0.0062 (19)
C15A0.063 (3)0.108 (5)0.026 (2)0.017 (3)0.0141 (17)0.007 (3)
C13B0.040 (5)0.056 (7)0.022 (3)0.016 (6)0.002 (3)0.003 (5)
C14B0.060 (5)0.067 (5)0.040 (4)0.027 (4)0.006 (3)0.005 (3)
C15B0.204 (18)0.040 (5)0.023 (5)0.010 (7)0.013 (6)0.003 (3)
C160.0264 (7)0.0397 (9)0.0324 (8)0.0063 (6)0.0085 (6)0.0043 (6)
C170.0440 (11)0.0479 (11)0.0454 (10)0.0156 (9)0.0077 (8)0.0055 (8)
C180.0374 (11)0.0641 (14)0.0657 (15)0.0142 (10)0.0264 (10)0.0232 (11)
P210.0373 (2)0.02489 (18)0.02055 (18)0.00273 (15)0.00356 (15)0.00162 (13)
S210.0305 (2)0.0330 (2)0.02438 (18)0.00355 (15)0.00056 (14)0.00304 (14)
O210.0367 (6)0.0460 (7)0.0303 (6)0.0092 (6)0.0008 (5)0.0067 (5)
O220.0445 (8)0.0541 (9)0.0389 (7)0.0219 (7)0.0019 (6)0.0052 (6)
O230.0420 (7)0.0285 (6)0.0311 (6)0.0017 (5)0.0007 (5)0.0029 (4)
O240.0466 (7)0.0363 (6)0.0292 (6)0.0050 (5)0.0018 (5)0.0085 (5)
O250.0428 (7)0.0324 (6)0.0314 (6)0.0025 (5)0.0113 (5)0.0040 (5)
C210.0405 (12)0.0239 (9)0.0218 (9)0.0000.0021 (8)0.000
C220.0380 (8)0.0272 (7)0.0232 (7)0.0022 (6)0.0043 (6)0.0002 (5)
C230.0459 (10)0.0366 (9)0.0361 (9)0.0067 (8)0.0066 (7)0.0008 (7)
C240.0525 (13)0.0592 (13)0.0511 (12)0.0067 (11)0.0039 (10)0.0196 (10)
C250.0864 (18)0.0602 (15)0.0407 (11)0.0310 (13)0.0218 (11)0.0125 (10)
C260.0655 (13)0.0310 (8)0.0402 (10)0.0037 (8)0.0233 (9)0.0055 (7)
C270.0712 (17)0.0718 (17)0.0648 (16)0.0309 (14)0.0225 (13)0.0053 (13)
C280.0781 (18)0.0714 (17)0.0367 (11)0.0045 (14)0.0095 (11)0.0169 (11)
P310.0284 (2)0.02564 (18)0.02487 (19)0.00070 (14)0.00601 (14)0.00023 (13)
S310.02421 (18)0.03015 (18)0.02341 (17)0.00079 (13)0.00221 (13)0.00124 (13)
O310.0290 (6)0.0402 (6)0.0337 (6)0.0092 (5)0.0046 (4)0.0030 (5)
O320.0389 (7)0.0492 (8)0.0324 (6)0.0130 (6)0.0009 (5)0.0106 (6)
O330.0403 (7)0.0253 (5)0.0408 (7)0.0026 (5)0.0106 (5)0.0044 (5)
O340.0275 (6)0.0364 (6)0.0324 (6)0.0044 (5)0.0027 (4)0.0065 (5)
O350.0371 (7)0.0477 (7)0.0260 (6)0.0036 (6)0.0050 (5)0.0080 (5)
C310.0299 (10)0.0223 (9)0.0262 (9)0.0000.0078 (8)0.000
C320.0277 (7)0.0254 (7)0.0246 (7)0.0004 (5)0.0050 (5)0.0024 (5)
C330.0288 (8)0.0432 (10)0.0427 (10)0.0040 (7)0.0009 (7)0.0058 (8)
C340.0490 (12)0.0518 (13)0.0599 (14)0.0010 (10)0.0148 (10)0.0068 (10)
C350.0319 (11)0.143 (3)0.0760 (18)0.0151 (15)0.0172 (11)0.024 (2)
C36A0.044 (4)0.093 (7)0.043 (4)0.010 (4)0.005 (3)0.037 (4)
C37A0.072 (3)0.042 (2)0.058 (3)0.0094 (19)0.012 (2)0.0191 (19)
C38A0.159 (7)0.102 (4)0.085 (4)0.069 (5)0.086 (5)0.039 (4)
C36B0.072 (9)0.045 (5)0.033 (5)0.002 (4)0.012 (5)0.001 (4)
C37B0.108 (8)0.077 (6)0.025 (3)0.023 (5)0.008 (4)0.009 (3)
C38B0.25 (2)0.050 (6)0.098 (11)0.035 (10)0.110 (13)0.012 (6)
Geometric parameters (Å, º) top
P1—O31.4722 (12)C17—H17B0.9800
P1—O51.5640 (13)C17—H17C0.9800
P1—O41.5693 (12)C18—H18A0.9800
P1—C21.8074 (16)C18—H18B0.9800
S1—O21.4359 (13)C18—H18C0.9800
S1—O11.4407 (13)P21—O231.4721 (13)
S1—C21.7751 (16)P21—O251.5635 (14)
S1—C11.7884 (12)P21—O241.5658 (13)
O4—C3A1.433 (5)P21—C221.8085 (16)
O4—C3B1.520 (6)S21—O221.4355 (14)
O5—C61.471 (2)S21—O211.4394 (13)
C1—S1i1.7884 (12)S21—C221.7742 (16)
C1—H10.9601S21—C211.7857 (12)
C2—H2A0.9900O24—C231.464 (2)
C2—H2B0.9900O25—C261.465 (2)
C3A—C5A1.505 (6)C21—S21iii1.7857 (12)
C3A—C4A1.519 (6)C21—H210.9601
C3A—H3A1.0000C22—H22A0.9900
C4A—H4AA0.9800C22—H22B0.9900
C4A—H4AB0.9800C23—C241.501 (3)
C4A—H4AC0.9800C23—C251.512 (3)
C5A—H5AA0.9800C23—H231.0000
C5A—H5AB0.9800C24—H24A0.9800
C5A—H5AC0.9800C24—H24B0.9800
C3B—C5B1.484 (8)C24—H24C0.9800
C3B—C4B1.521 (7)C25—H25A0.9800
C3B—H3B1.0000C25—H25B0.9800
C4B—H4BA0.9800C25—H25C0.9800
C4B—H4BB0.9800C26—C271.497 (4)
C4B—H4BC0.9800C26—C281.507 (3)
C5B—H5BA0.9800C26—H261.0000
C5B—H5BB0.9800C27—H27A0.9800
C5B—H5BC0.9800C27—H27B0.9800
C6—C71.502 (3)C27—H27C0.9800
C6—C81.508 (3)C28—H28A0.9800
C6—H61.0000C28—H28B0.9800
C7—H7A0.9800C28—H28C0.9800
C7—H7B0.9800P31—O331.4706 (13)
C7—H7C0.9800P31—O351.5629 (13)
C8—H8A0.9800P31—O341.5728 (12)
C8—H8B0.9800P31—C321.8127 (15)
C8—H8C0.9800S31—O321.4355 (13)
P11—O131.4729 (12)S31—O311.4423 (13)
P11—O151.5656 (13)S31—C321.7735 (15)
P11—O141.5671 (12)S31—C311.7879 (12)
P11—C121.8058 (15)O34—C331.477 (2)
S11—O121.4374 (13)O35—C36B1.46 (2)
S11—O111.4419 (12)O35—C36A1.473 (10)
S11—C121.7740 (14)C31—S31iv1.7879 (12)
S11—C111.7929 (11)C31—H310.9598
O14—C13B1.470 (16)C32—H32A0.9900
O14—C13A1.498 (8)C32—H32B0.9900
O15—C161.4814 (19)C33—C341.495 (3)
C11—S11ii1.7929 (11)C33—C351.507 (3)
C11—H110.9600C33—H331.0000
C12—H12A0.9900C34—H34A0.9800
C12—H12B0.9900C34—H34B0.9800
C13A—C15A1.487 (7)C34—H34C0.9800
C13A—C14A1.505 (7)C35—H35A0.9800
C13A—H13A1.0000C35—H35B0.9800
C14A—H14A0.9800C35—H35C0.9800
C14A—H14B0.9800C36A—C38A1.478 (13)
C14A—H14C0.9800C36A—C37A1.498 (10)
C15A—H15A0.9800C36A—H36A1.0000
C15A—H15B0.9800C37A—H37A0.9800
C15A—H15C0.9800C37A—H37B0.9800
C13B—C15B1.507 (13)C37A—H37C0.9800
C13B—C14B1.515 (12)C38A—H38A0.9800
C13B—H13B1.0000C38A—H38B0.9800
C14B—H14D0.9800C38A—H38C0.9800
C14B—H14E0.9800C36B—C38B1.429 (19)
C14B—H14F0.9800C36B—C37B1.536 (15)
C15B—H15D0.9800C36B—H36B1.0000
C15B—H15E0.9800C37B—H37D0.9800
C15B—H15F0.9800C37B—H37E0.9800
C16—C171.499 (3)C37B—H37F0.9800
C16—C181.508 (3)C38B—H38D0.9800
C16—H161.0000C38B—H38E0.9800
C17—H17A0.9800C38B—H38F0.9800
O3—P1—O5117.30 (7)C16—C18—H18C109.5
O3—P1—O4115.03 (7)H18A—C18—H18C109.5
O5—P1—O4103.57 (7)H18B—C18—H18C109.5
O3—P1—C2113.86 (7)O23—P21—O25117.09 (8)
O5—P1—C2101.31 (7)O23—P21—O24115.20 (8)
O4—P1—C2103.95 (7)O25—P21—O24103.38 (7)
O2—S1—O1119.43 (8)O23—P21—C22113.90 (7)
O2—S1—C2109.54 (8)O25—P21—C22101.09 (8)
O1—S1—C2107.34 (8)O24—P21—C22104.37 (7)
O2—S1—C1105.49 (9)O22—S21—O21119.48 (9)
O1—S1—C1107.82 (7)O22—S21—C22109.34 (8)
C2—S1—C1106.54 (6)O21—S21—C22107.24 (8)
C3A—O4—P1124.3 (2)O22—S21—C21105.40 (9)
C3B—O4—P1120.9 (2)O21—S21—C21107.91 (7)
C6—O5—P1122.74 (11)C22—S21—C21106.84 (6)
S1i—C1—S1117.41 (12)C23—O24—P21124.19 (12)
S1i—C1—H1108.0C26—O25—P21122.50 (13)
S1—C1—H1107.9S21iii—C21—S21116.99 (12)
S1—C2—P1114.63 (9)S21iii—C21—H21108.1
S1—C2—H2A108.6S21—C21—H21108.0
P1—C2—H2A108.6S21—C22—P21114.42 (9)
S1—C2—H2B108.6S21—C22—H22A108.7
P1—C2—H2B108.6P21—C22—H22A108.7
H2A—C2—H2B107.6S21—C22—H22B108.7
O4—C3A—C5A107.0 (4)P21—C22—H22B108.7
O4—C3A—C4A106.7 (3)H22A—C22—H22B107.6
C5A—C3A—C4A110.6 (4)O24—C23—C24109.23 (17)
O4—C3A—H3A110.8O24—C23—C25106.07 (18)
C5A—C3A—H3A110.8C24—C23—C25112.17 (18)
C4A—C3A—H3A110.8O24—C23—H23109.8
C5B—C3B—O4109.7 (5)C24—C23—H23109.8
C5B—C3B—C4B114.0 (5)C25—C23—H23109.8
O4—C3B—C4B106.2 (4)C23—C24—H24A109.5
C5B—C3B—H3B109.0C23—C24—H24B109.5
O4—C3B—H3B109.0H24A—C24—H24B109.5
C4B—C3B—H3B109.0C23—C24—H24C109.5
C3B—C4B—H4BA109.5H24A—C24—H24C109.5
C3B—C4B—H4BB109.5H24B—C24—H24C109.5
H4BA—C4B—H4BB109.5C23—C25—H25A109.5
C3B—C4B—H4BC109.5C23—C25—H25B109.5
H4BA—C4B—H4BC109.5H25A—C25—H25B109.5
H4BB—C4B—H4BC109.5C23—C25—H25C109.5
C3B—C5B—H5BA109.5H25A—C25—H25C109.5
C3B—C5B—H5BB109.5H25B—C25—H25C109.5
H5BA—C5B—H5BB109.5O25—C26—C27105.1 (2)
C3B—C5B—H5BC109.5O25—C26—C28110.05 (18)
H5BA—C5B—H5BC109.5C27—C26—C28113.92 (19)
H5BB—C5B—H5BC109.5O25—C26—H26109.2
O5—C6—C7105.20 (15)C27—C26—H26109.2
O5—C6—C8109.44 (17)C28—C26—H26109.2
C7—C6—C8113.71 (19)C26—C27—H27A109.5
O5—C6—H6109.5C26—C27—H27B109.5
C7—C6—H6109.5H27A—C27—H27B109.5
C8—C6—H6109.5C26—C27—H27C109.5
C6—C7—H7A109.5H27A—C27—H27C109.5
C6—C7—H7B109.5H27B—C27—H27C109.5
H7A—C7—H7B109.5C26—C28—H28A109.5
C6—C7—H7C109.5C26—C28—H28B109.5
H7A—C7—H7C109.5H28A—C28—H28B109.5
H7B—C7—H7C109.5C26—C28—H28C109.5
C6—C8—H8A109.5H28A—C28—H28C109.5
C6—C8—H8B109.5H28B—C28—H28C109.5
H8A—C8—H8B109.5O33—P31—O35117.38 (8)
C6—C8—H8C109.5O33—P31—O34114.90 (7)
H8A—C8—H8C109.5O35—P31—O34102.73 (7)
H8B—C8—H8C109.5O33—P31—C32113.16 (7)
O13—P11—O15117.52 (7)O35—P31—C32102.53 (7)
O13—P11—O14114.40 (7)O34—P31—C32104.49 (7)
O15—P11—O14103.43 (7)O32—S31—O31119.12 (8)
O13—P11—C12112.81 (7)O32—S31—C32109.16 (8)
O15—P11—C12102.35 (7)O31—S31—C32107.16 (8)
O14—P11—C12104.81 (7)O32—S31—C31105.98 (9)
O12—S11—O11119.22 (8)O31—S31—C31107.85 (7)
O12—S11—C12109.26 (7)C32—S31—C31107.01 (6)
O11—S11—C12107.12 (8)C33—O34—P31123.92 (11)
O12—S11—C11105.72 (8)C36B—O35—P31122.8 (8)
O11—S11—C11107.88 (6)C36A—O35—P31118.6 (4)
C12—S11—C11107.06 (6)S31—C31—S31iv117.09 (12)
C13B—O14—P11129.3 (6)S31—C31—H31108.0
C13A—O14—P11120.2 (2)S31iv—C31—H31108.0
C16—O15—P11119.94 (11)S31—C32—P31115.75 (8)
S11ii—C11—S11116.55 (11)S31—C32—H32A108.3
S11ii—C11—H11108.2P31—C32—H32A108.3
S11—C11—H11108.1S31—C32—H32B108.3
S11—C12—P11114.98 (8)P31—C32—H32B108.3
S11—C12—H12A108.5H32A—C32—H32B107.4
P11—C12—H12A108.5O34—C33—C34108.60 (16)
S11—C12—H12B108.5O34—C33—C35105.06 (18)
P11—C12—H12B108.5C34—C33—C35113.9 (2)
H12A—C12—H12B107.5O34—C33—H33109.7
C15A—C13A—O14107.6 (6)C34—C33—H33109.7
C15A—C13A—C14A113.9 (5)C35—C33—H33109.7
O14—C13A—C14A104.6 (4)C33—C34—H34A109.5
C15A—C13A—H13A110.2C33—C34—H34B109.5
O14—C13A—H13A110.2H34A—C34—H34B109.5
C14A—C13A—H13A110.2C33—C34—H34C109.5
O14—C13B—C15B98.0 (11)H34A—C34—H34C109.5
O14—C13B—C14B115.5 (9)H34B—C34—H34C109.5
C15B—C13B—C14B108.3 (9)C33—C35—H35A109.5
O14—C13B—H13B111.4C33—C35—H35B109.5
C15B—C13B—H13B111.4H35A—C35—H35B109.5
C14B—C13B—H13B111.4C33—C35—H35C109.5
C13B—C14B—H14D109.5H35A—C35—H35C109.5
C13B—C14B—H14E109.5H35B—C35—H35C109.5
H14D—C14B—H14E109.5O35—C36A—C38A106.8 (8)
C13B—C14B—H14F109.5O35—C36A—C37A107.3 (7)
H14D—C14B—H14F109.5C38A—C36A—C37A111.9 (7)
H14E—C14B—H14F109.5O35—C36A—H36A110.2
C13B—C15B—H15D109.5C38A—C36A—H36A110.2
C13B—C15B—H15E109.5C37A—C36A—H36A110.2
H15D—C15B—H15E109.5C38B—C36B—O35112.1 (16)
C13B—C15B—H15F109.5C38B—C36B—C37B112.5 (14)
H15D—C15B—H15F109.5O35—C36B—C37B111.0 (14)
H15E—C15B—H15F109.5C38B—C36B—H36B107.0
O15—C16—C17107.69 (14)O35—C36B—H36B107.0
O15—C16—C18108.01 (15)C37B—C36B—H36B107.0
C17—C16—C18112.54 (17)C36B—C37B—H37D109.5
O15—C16—H16109.5C36B—C37B—H37E109.5
C17—C16—H16109.5H37D—C37B—H37E109.5
C18—C16—H16109.5C36B—C37B—H37F109.5
C16—C17—H17A109.5H37D—C37B—H37F109.5
C16—C17—H17B109.5H37E—C37B—H37F109.5
H17A—C17—H17B109.5C36B—C38B—H38D109.5
C16—C17—H17C109.5C36B—C38B—H38E109.5
H17A—C17—H17C109.5H38D—C38B—H38E109.5
H17B—C17—H17C109.5C36B—C38B—H38F109.5
C16—C18—H18A109.5H38D—C38B—H38F109.5
C16—C18—H18B109.5H38E—C38B—H38F109.5
H18A—C18—H18B109.5
O3—P1—O4—C3A17.8 (3)C13A—O14—C13B—C14B161 (3)
O5—P1—O4—C3A147.1 (2)P11—O14—C13B—C14B135.4 (7)
C2—P1—O4—C3A107.4 (2)P11—O15—C16—C17137.88 (14)
O3—P1—O4—C3B44.4 (3)P11—O15—C16—C18100.33 (17)
O5—P1—O4—C3B173.7 (3)O23—P21—O24—C2325.61 (16)
C2—P1—O4—C3B80.7 (3)O25—P21—O24—C23154.60 (14)
O3—P1—O5—C632.28 (16)C22—P21—O24—C23100.03 (14)
O4—P1—O5—C695.61 (14)O23—P21—O25—C2636.62 (17)
C2—P1—O5—C6156.86 (14)O24—P21—O25—C2691.20 (15)
O2—S1—C1—S1i176.09 (6)C22—P21—O25—C26160.95 (14)
O1—S1—C1—S1i47.44 (7)O22—S21—C21—S21iii176.05 (7)
C2—S1—C1—S1i67.53 (6)O21—S21—C21—S21iii47.33 (7)
O2—S1—C2—P139.36 (12)C22—S21—C21—S21iii67.70 (6)
O1—S1—C2—P1170.43 (8)O22—S21—C22—P2140.73 (13)
C1—S1—C2—P174.28 (11)O21—S21—C22—P21171.65 (9)
O3—P1—C2—S142.99 (12)C21—S21—C22—P2172.86 (11)
O5—P1—C2—S183.87 (10)O23—P21—C22—S2144.75 (12)
O4—P1—C2—S1168.90 (8)O25—P21—C22—S2181.72 (10)
C3B—O4—C3A—C5A113.5 (10)O24—P21—C22—S21171.21 (9)
P1—O4—C3A—C5A157.8 (3)P21—O24—C23—C2497.35 (18)
C3B—O4—C3A—C4A4.9 (8)P21—O24—C23—C25141.56 (15)
P1—O4—C3A—C4A83.8 (4)P21—O25—C26—C27152.51 (16)
C3A—O4—C3B—C5B17.7 (7)P21—O25—C26—C2884.4 (2)
P1—O4—C3B—C5B88.2 (5)O33—P31—O34—C3318.92 (16)
C3A—O4—C3B—C4B105.9 (11)O35—P31—O34—C33147.58 (14)
P1—O4—C3B—C4B148.3 (4)C32—P31—O34—C33105.67 (14)
P1—O5—C6—C7151.72 (17)O33—P31—O35—C36B64.7 (10)
P1—O5—C6—C885.76 (19)O34—P31—O35—C36B62.3 (10)
O13—P11—O14—C13B33.8 (6)C32—P31—O35—C36B170.6 (10)
O15—P11—O14—C13B162.9 (5)O33—P31—O35—C36A55.6 (6)
C12—P11—O14—C13B90.3 (5)O34—P31—O35—C36A71.5 (6)
O13—P11—O14—C13A16.2 (3)C32—P31—O35—C36A179.7 (6)
O15—P11—O14—C13A145.3 (3)O32—S31—C31—S31iv174.83 (6)
C12—P11—O14—C13A107.9 (3)O31—S31—C31—S31iv46.22 (6)
O13—P11—O15—C1657.69 (14)C32—S31—C31—S31iv68.78 (6)
O14—P11—O15—C1669.41 (13)O32—S31—C32—P3145.23 (12)
C12—P11—O15—C16178.15 (12)O31—S31—C32—P31175.50 (8)
O12—S11—C11—S11ii175.24 (6)C31—S31—C32—P3169.04 (10)
O11—S11—C11—S11ii46.65 (6)O33—P31—C32—S3141.17 (12)
C12—S11—C11—S11ii68.35 (6)O35—P31—C32—S3186.24 (10)
O12—S11—C12—P1142.73 (11)O34—P31—C32—S31166.86 (8)
O11—S11—C12—P11173.17 (8)P31—O34—C33—C3497.55 (18)
C11—S11—C12—P1171.32 (10)P31—O34—C33—C35140.2 (2)
O13—P11—C12—S1141.33 (11)C36B—O35—C36A—C38A10 (8)
O15—P11—C12—S1185.91 (9)P31—O35—C36A—C38A110.2 (6)
O14—P11—C12—S11166.40 (8)C36B—O35—C36A—C37A110 (8)
C13B—O14—C13A—C15A95 (3)P31—O35—C36A—C37A129.6 (5)
P11—O14—C13A—C15A137.8 (4)C36A—O35—C36B—C38B26 (7)
C13B—O14—C13A—C14A26 (2)P31—O35—C36B—C38B90.2 (18)
P11—O14—C13A—C14A100.7 (4)C36A—O35—C36B—C37B153 (10)
C13A—O14—C13B—C15B47 (2)P31—O35—C36B—C37B143.0 (10)
P11—O14—C13B—C15B109.8 (8)
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x+3/2, y, z+3/2; (iii) x+1/2, y, z+3/2; (iv) x+3/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H34O10P2S2
Mr500.50
Crystal system, space groupMonoclinic, P2/n
Temperature (K)180
a, b, c (Å)21.7314 (17), 10.2307 (8), 21.8150 (17)
β (°) 92.922 (5)
V3)4843.8 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.40
Crystal size (mm)0.40 × 0.25 × 0.13
Data collection
DiffractometerBruker SMART APEX II
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2005)
Tmin, Tmax0.857, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections
53365, 14085, 12471
Rint0.052
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.117, 1.08
No. of reflections14085
No. of parameters627
No. of restraints9
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.61

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Sheldrick, 1994), SHELXL97.

 

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