Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702507X/pk2026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702507X/pk2026Isup2.hkl |
CCDC reference: 651535
The synthesis of (I) was reported earlier (Hadd et al., 2001). Crystals were grown from diethyl ether.
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.
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).
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.
C15H34O10P2S2 | F(000) = 2128 |
Mr = 500.50 | Dx = 1.373 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yac | Cell parameters from 7807 reflections |
a = 21.7314 (17) Å | θ = 2.9–30.5° |
b = 10.2307 (8) Å | µ = 0.40 mm−1 |
c = 21.8150 (17) Å | T = 180 K |
β = 92.922 (5)° | Block, colorless |
V = 4843.8 (7) Å3 | 0.40 × 0.25 × 0.13 mm |
Z = 8 |
Bruker SMART APEX II diffractometer | 14085 independent reflections |
Radiation source: fine-focus sealed tube | 12471 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 8.3 pixels mm-1 | θmax = 30.0°, θmin = 2.9° |
ω and φ scans | h = −30→30 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2005) | k = −14→14 |
Tmin = 0.857, Tmax = 0.950 | l = −30→30 |
53365 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-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 parameters | Δρmax = 0.50 e Å−3 |
9 restraints | Δρmin = −0.61 e Å−3 |
C15H34O10P2S2 | V = 4843.8 (7) Å3 |
Mr = 500.50 | Z = 8 |
Monoclinic, P2/n | Mo Kα radiation |
a = 21.7314 (17) Å | µ = 0.40 mm−1 |
b = 10.2307 (8) Å | T = 180 K |
c = 21.8150 (17) Å | 0.40 × 0.25 × 0.13 mm |
β = 92.922 (5)° |
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 = 0.950 | Rint = 0.052 |
53365 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 9 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.50 e Å−3 |
14085 reflections | Δρmin = −0.61 e Å−3 |
627 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.085776 (19) | 0.12874 (4) | 0.26172 (2) | 0.02586 (9) | |
S1 | 0.217544 (18) | 0.10297 (4) | 0.310518 (18) | 0.02721 (8) | |
O1 | 0.26109 (6) | 0.00310 (15) | 0.32980 (6) | 0.0377 (3) | |
O2 | 0.19921 (6) | 0.19881 (14) | 0.35408 (6) | 0.0404 (3) | |
O3 | 0.10166 (6) | 0.25460 (11) | 0.23388 (6) | 0.0317 (2) | |
O4 | 0.03976 (6) | 0.04176 (12) | 0.22177 (6) | 0.0337 (3) | |
O5 | 0.05649 (6) | 0.13298 (12) | 0.32571 (6) | 0.0333 (3) | |
C1 | 0.2500 | 0.1938 (2) | 0.2500 | 0.0256 (4) | |
H1 | 0.2816 | 0.2494 | 0.2680 | 0.031* | |
C2 | 0.15125 (7) | 0.02299 (15) | 0.27774 (8) | 0.0281 (3) | |
H2A | 0.1390 | −0.0468 | 0.3061 | 0.034* | |
H2B | 0.1623 | −0.0194 | 0.2390 | 0.034* | |
C3A | 0.0269 (2) | 0.0588 (4) | 0.1572 (2) | 0.0368 (9) | 0.57 |
H3A | 0.0264 | 0.1537 | 0.1461 | 0.044* | 0.57 |
C4A | 0.0772 (2) | −0.0128 (8) | 0.1250 (2) | 0.0779 (17) | 0.57 |
H4AA | 0.1166 | 0.0320 | 0.1333 | 0.117* | 0.57 |
H4AB | 0.0673 | −0.0137 | 0.0806 | 0.117* | 0.57 |
H4AC | 0.0802 | −0.1028 | 0.1402 | 0.117* | 0.57 |
C5A | −0.03493 (17) | −0.0028 (7) | 0.1420 (2) | 0.0652 (13) | 0.57 |
H5AA | −0.0668 | 0.0440 | 0.1635 | 0.098* | 0.57 |
H5AB | −0.0341 | −0.0945 | 0.1550 | 0.098* | 0.57 |
H5AC | −0.0442 | 0.0019 | 0.0976 | 0.098* | 0.57 |
C3B | 0.0476 (3) | 0.0236 (6) | 0.1535 (3) | 0.0359 (12) | 0.43 |
H3B | 0.0925 | 0.0282 | 0.1454 | 0.043* | 0.43 |
C4B | 0.0240 (3) | −0.1129 (5) | 0.1378 (3) | 0.0572 (14) | 0.43 |
H4BA | 0.0222 | −0.1249 | 0.0932 | 0.086* | 0.43 |
H4BB | −0.0174 | −0.1238 | 0.1531 | 0.086* | 0.43 |
H4BC | 0.0518 | −0.1780 | 0.1571 | 0.086* | 0.43 |
C5B | 0.0147 (4) | 0.1294 (6) | 0.1186 (3) | 0.0661 (17) | 0.43 |
H5BA | 0.0302 | 0.2144 | 0.1332 | 0.099* | 0.43 |
H5BB | −0.0295 | 0.1234 | 0.1249 | 0.099* | 0.43 |
H5BC | 0.0218 | 0.1201 | 0.0748 | 0.099* | 0.43 |
C6 | 0.01642 (8) | 0.24022 (18) | 0.34433 (9) | 0.0361 (4) | |
H6 | 0.0306 | 0.3241 | 0.3262 | 0.043* | |
C7 | 0.02495 (14) | 0.2464 (3) | 0.41301 (11) | 0.0635 (7) | |
H7A | 0.0690 | 0.2523 | 0.4248 | 0.095* | |
H7B | 0.0078 | 0.1674 | 0.4309 | 0.095* | |
H7C | 0.0037 | 0.3235 | 0.4281 | 0.095* | |
C8 | −0.04901 (10) | 0.2129 (3) | 0.32162 (13) | 0.0566 (6) | |
H8A | −0.0511 | 0.2082 | 0.2767 | 0.085* | |
H8B | −0.0759 | 0.2833 | 0.3349 | 0.085* | |
H8C | −0.0625 | 0.1296 | 0.3385 | 0.085* | |
P11 | 0.882618 (18) | 0.37244 (4) | 0.659619 (18) | 0.02439 (8) | |
S11 | 0.816104 (16) | 0.40065 (4) | 0.777057 (16) | 0.02385 (8) | |
O11 | 0.79536 (5) | 0.50171 (14) | 0.81719 (5) | 0.0351 (3) | |
O12 | 0.86010 (6) | 0.30603 (15) | 0.80066 (6) | 0.0393 (3) | |
O13 | 0.84913 (6) | 0.24861 (12) | 0.64917 (6) | 0.0325 (2) | |
O14 | 0.88947 (6) | 0.45678 (13) | 0.60039 (5) | 0.0353 (3) | |
O15 | 0.95002 (5) | 0.36449 (12) | 0.68835 (5) | 0.0300 (2) | |
C11 | 0.7500 | 0.3085 (2) | 0.7500 | 0.0229 (4) | |
H11 | 0.7379 | 0.2529 | 0.7827 | 0.027* | |
C12 | 0.84566 (7) | 0.47943 (15) | 0.71235 (7) | 0.0242 (3) | |
H12A | 0.8758 | 0.5465 | 0.7270 | 0.029* | |
H12B | 0.8114 | 0.5253 | 0.6898 | 0.029* | |
C13A | 0.8499 (4) | 0.4293 (5) | 0.5436 (3) | 0.0325 (10) | 0.68 |
H13A | 0.8315 | 0.3400 | 0.5459 | 0.039* | 0.68 |
C14A | 0.80000 (19) | 0.5314 (5) | 0.54370 (17) | 0.0664 (11) | 0.68 |
H14A | 0.7737 | 0.5154 | 0.5781 | 0.100* | 0.68 |
H14B | 0.7751 | 0.5270 | 0.5050 | 0.100* | 0.68 |
H14C | 0.8187 | 0.6182 | 0.5481 | 0.100* | 0.68 |
C15A | 0.8897 (3) | 0.4383 (7) | 0.4904 (3) | 0.0649 (17) | 0.68 |
H15A | 0.9233 | 0.3747 | 0.4953 | 0.097* | 0.68 |
H15B | 0.9069 | 0.5266 | 0.4882 | 0.097* | 0.68 |
H15C | 0.8652 | 0.4194 | 0.4525 | 0.097* | 0.68 |
C13B | 0.8467 (8) | 0.4713 (10) | 0.5464 (6) | 0.039 (3) | 0.32 |
H13B | 0.8065 | 0.4266 | 0.5527 | 0.047* | 0.32 |
C14B | 0.8369 (4) | 0.6099 (8) | 0.5236 (3) | 0.0562 (19) | 0.32 |
H14D | 0.8138 | 0.6593 | 0.5532 | 0.084* | 0.32 |
H14E | 0.8138 | 0.6084 | 0.4838 | 0.084* | 0.32 |
H14F | 0.8770 | 0.6517 | 0.5188 | 0.084* | 0.32 |
C15B | 0.8838 (9) | 0.3987 (11) | 0.5009 (5) | 0.090 (6) | 0.32 |
H15D | 0.8921 | 0.3098 | 0.5158 | 0.135* | 0.32 |
H15E | 0.9229 | 0.4443 | 0.4960 | 0.135* | 0.32 |
H15F | 0.8606 | 0.3948 | 0.4612 | 0.135* | 0.32 |
C16 | 0.99712 (8) | 0.28756 (18) | 0.65737 (8) | 0.0326 (3) | |
H16 | 0.9763 | 0.2246 | 0.6280 | 0.039* | |
C17 | 1.03399 (10) | 0.2135 (2) | 0.70582 (10) | 0.0456 (5) | |
H17A | 1.0062 | 0.1608 | 0.7298 | 0.068* | |
H17B | 1.0565 | 0.2752 | 0.7330 | 0.068* | |
H17C | 1.0633 | 0.1560 | 0.6863 | 0.068* | |
C18 | 1.03599 (10) | 0.3813 (2) | 0.62260 (12) | 0.0549 (6) | |
H18A | 1.0102 | 0.4251 | 0.5906 | 0.082* | |
H18B | 1.0690 | 0.3331 | 0.6036 | 0.082* | |
H18C | 1.0540 | 0.4468 | 0.6510 | 0.082* | |
P21 | 0.24751 (2) | 0.86489 (4) | 0.913720 (18) | 0.02752 (9) | |
S21 | 0.191320 (19) | 0.89188 (4) | 0.785262 (18) | 0.02933 (9) | |
O21 | 0.17004 (6) | 0.99185 (15) | 0.74286 (6) | 0.0377 (3) | |
O22 | 0.14858 (7) | 0.79628 (15) | 0.80573 (7) | 0.0458 (3) | |
O23 | 0.27713 (6) | 0.74223 (12) | 0.89584 (6) | 0.0339 (3) | |
O24 | 0.28696 (6) | 0.95280 (13) | 0.95945 (6) | 0.0374 (3) | |
O25 | 0.18443 (6) | 0.85339 (13) | 0.94472 (6) | 0.0352 (3) | |
C21 | 0.2500 | 0.8007 (2) | 0.7500 | 0.0289 (4) | |
H21 | 0.2305 | 0.7451 | 0.7194 | 0.035* | |
C22 | 0.22707 (8) | 0.97182 (16) | 0.84988 (7) | 0.0294 (3) | |
H22A | 0.1989 | 1.0402 | 0.8640 | 0.035* | |
H22B | 0.2648 | 1.0159 | 0.8370 | 0.035* | |
C23 | 0.35436 (10) | 0.95121 (19) | 0.96529 (9) | 0.0398 (4) | |
H23 | 0.3701 | 0.8658 | 0.9502 | 0.048* | |
C24 | 0.37912 (12) | 1.0610 (2) | 0.92810 (11) | 0.0542 (5) | |
H24A | 0.3679 | 1.0465 | 0.8845 | 0.081* | |
H24B | 0.4241 | 1.0641 | 0.9342 | 0.081* | |
H24C | 0.3615 | 1.1439 | 0.9413 | 0.081* | |
C25 | 0.37131 (14) | 0.9660 (3) | 1.03304 (10) | 0.0633 (7) | |
H25A | 0.3520 | 0.8958 | 1.0558 | 0.095* | |
H25B | 0.3568 | 1.0508 | 1.0474 | 0.095* | |
H25C | 0.4162 | 0.9609 | 1.0398 | 0.095* | |
C26 | 0.17096 (11) | 0.74753 (19) | 0.98726 (9) | 0.0448 (5) | |
H26 | 0.1911 | 0.6654 | 0.9737 | 0.054* | |
C27 | 0.10246 (14) | 0.7309 (3) | 0.98155 (14) | 0.0686 (8) | |
H27A | 0.0894 | 0.7178 | 0.9383 | 0.103* | |
H27B | 0.0825 | 0.8093 | 0.9971 | 0.103* | |
H27C | 0.0906 | 0.6548 | 1.0055 | 0.103* | |
C28 | 0.19542 (14) | 0.7815 (3) | 1.05117 (10) | 0.0619 (7) | |
H28A | 0.2404 | 0.7879 | 1.0518 | 0.093* | |
H28B | 0.1836 | 0.7133 | 1.0798 | 0.093* | |
H28C | 0.1782 | 0.8655 | 1.0634 | 0.093* | |
P31 | 0.84281 (2) | 0.63324 (4) | 0.119898 (18) | 0.02613 (9) | |
S31 | 0.722851 (17) | 0.60354 (4) | 0.184137 (17) | 0.02589 (8) | |
O31 | 0.68284 (5) | 0.50178 (14) | 0.20468 (5) | 0.0342 (2) | |
O32 | 0.69880 (6) | 0.69798 (14) | 0.14054 (6) | 0.0402 (3) | |
O33 | 0.85417 (6) | 0.75450 (12) | 0.15487 (6) | 0.0352 (3) | |
O34 | 0.90134 (5) | 0.54539 (12) | 0.11237 (6) | 0.0321 (2) | |
O35 | 0.81563 (6) | 0.64658 (14) | 0.05247 (6) | 0.0368 (3) | |
C31 | 0.7500 | 0.6947 (2) | 0.2500 | 0.0259 (4) | |
H31 | 0.7172 | 0.7503 | 0.2620 | 0.031* | |
C32 | 0.78787 (7) | 0.52589 (15) | 0.15428 (7) | 0.0258 (3) | |
H32A | 0.7731 | 0.4616 | 0.1230 | 0.031* | |
H32B | 0.8096 | 0.4767 | 0.1879 | 0.031* | |
C33 | 0.95852 (8) | 0.5560 (2) | 0.15169 (9) | 0.0383 (4) | |
H33 | 0.9611 | 0.6447 | 0.1709 | 0.046* | |
C34 | 0.95734 (11) | 0.4539 (2) | 0.20065 (11) | 0.0542 (6) | |
H34A | 0.9230 | 0.4711 | 0.2269 | 0.081* | |
H34B | 0.9962 | 0.4561 | 0.2255 | 0.081* | |
H34C | 0.9521 | 0.3676 | 0.1816 | 0.081* | |
C35 | 1.01006 (11) | 0.5392 (4) | 0.10867 (14) | 0.0830 (11) | |
H35A | 1.0074 | 0.6079 | 0.0773 | 0.125* | |
H35B | 1.0066 | 0.4534 | 0.0888 | 0.125* | |
H35C | 1.0498 | 0.5455 | 0.1319 | 0.125* | |
C36A | 0.8487 (5) | 0.7282 (12) | 0.0093 (4) | 0.060 (3) | 0.65 |
H36A | 0.8823 | 0.7784 | 0.0317 | 0.072* | 0.65 |
C37A | 0.8027 (2) | 0.8201 (5) | −0.0206 (3) | 0.0573 (12) | 0.65 |
H37A | 0.7851 | 0.8754 | 0.0107 | 0.086* | 0.65 |
H37B | 0.7697 | 0.7698 | −0.0419 | 0.086* | 0.65 |
H37C | 0.8231 | 0.8751 | −0.0502 | 0.086* | 0.65 |
C38A | 0.8750 (4) | 0.6385 (7) | −0.0356 (3) | 0.113 (3) | 0.65 |
H38A | 0.9053 | 0.5811 | −0.0144 | 0.169* | 0.65 |
H38B | 0.8952 | 0.6894 | −0.0669 | 0.169* | 0.65 |
H38C | 0.8420 | 0.5855 | −0.0552 | 0.169* | 0.65 |
C36B | 0.8490 (13) | 0.7087 (18) | 0.0041 (7) | 0.050 (4) | 0.35 |
H36B | 0.8939 | 0.6990 | 0.0156 | 0.060* | 0.35 |
C37B | 0.8369 (6) | 0.6380 (10) | −0.0574 (3) | 0.070 (3) | 0.35 |
H37D | 0.8433 | 0.5439 | −0.0516 | 0.105* | 0.35 |
H37E | 0.8653 | 0.6710 | −0.0873 | 0.105* | 0.35 |
H37F | 0.7944 | 0.6540 | −0.0726 | 0.105* | 0.35 |
C38B | 0.8366 (10) | 0.8457 (11) | −0.0001 (7) | 0.129 (8) | 0.35 |
H38D | 0.8464 | 0.8869 | 0.0398 | 0.193* | 0.35 |
H38E | 0.7930 | 0.8594 | −0.0119 | 0.193* | 0.35 |
H38F | 0.8621 | 0.8847 | −0.0311 | 0.193* | 0.35 |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.02296 (18) | 0.02212 (17) | 0.0326 (2) | −0.00184 (13) | 0.00276 (14) | −0.00063 (14) |
S1 | 0.02454 (18) | 0.03144 (19) | 0.02572 (18) | 0.00067 (14) | 0.00205 (13) | −0.00022 (13) |
O1 | 0.0299 (6) | 0.0471 (7) | 0.0360 (6) | 0.0053 (5) | 0.0004 (5) | 0.0141 (6) |
O2 | 0.0374 (7) | 0.0495 (8) | 0.0346 (6) | −0.0019 (6) | 0.0058 (5) | −0.0155 (6) |
O3 | 0.0331 (6) | 0.0227 (5) | 0.0393 (6) | −0.0031 (4) | 0.0013 (5) | 0.0012 (4) |
O4 | 0.0309 (6) | 0.0335 (6) | 0.0365 (6) | −0.0089 (5) | 0.0001 (5) | −0.0007 (5) |
O5 | 0.0328 (6) | 0.0307 (6) | 0.0372 (6) | 0.0057 (5) | 0.0089 (5) | 0.0005 (5) |
C1 | 0.0236 (9) | 0.0224 (9) | 0.0309 (10) | 0.000 | 0.0013 (8) | 0.000 |
C2 | 0.0242 (7) | 0.0232 (7) | 0.0371 (8) | −0.0006 (5) | 0.0039 (6) | 0.0000 (6) |
C3A | 0.048 (3) | 0.0241 (19) | 0.0377 (19) | 0.0003 (15) | −0.0046 (18) | −0.0018 (15) |
C4A | 0.046 (2) | 0.147 (5) | 0.041 (2) | 0.012 (3) | 0.0058 (18) | −0.017 (3) |
C5A | 0.0305 (17) | 0.111 (4) | 0.053 (2) | −0.006 (2) | −0.0097 (15) | −0.019 (3) |
C3B | 0.046 (3) | 0.027 (3) | 0.035 (2) | −0.006 (2) | 0.003 (2) | −0.005 (2) |
C4B | 0.077 (4) | 0.038 (2) | 0.055 (3) | 0.001 (2) | −0.011 (3) | −0.014 (2) |
C5B | 0.100 (5) | 0.046 (3) | 0.050 (3) | 0.001 (3) | −0.014 (3) | 0.008 (2) |
C6 | 0.0325 (8) | 0.0344 (8) | 0.0421 (9) | 0.0092 (7) | 0.0083 (7) | 0.0002 (7) |
C7 | 0.0773 (18) | 0.0703 (16) | 0.0431 (12) | 0.0337 (14) | 0.0063 (11) | −0.0090 (11) |
C8 | 0.0305 (10) | 0.0675 (15) | 0.0716 (16) | 0.0085 (10) | 0.0020 (9) | 0.0118 (12) |
P11 | 0.02121 (18) | 0.02863 (19) | 0.02384 (18) | −0.00176 (14) | 0.00612 (13) | −0.00264 (13) |
S11 | 0.01977 (16) | 0.03162 (18) | 0.02031 (16) | −0.00039 (13) | 0.00258 (12) | −0.00054 (12) |
O11 | 0.0302 (6) | 0.0473 (7) | 0.0282 (6) | −0.0065 (5) | 0.0067 (4) | −0.0148 (5) |
O12 | 0.0268 (6) | 0.0555 (8) | 0.0353 (6) | 0.0076 (6) | 0.0001 (5) | 0.0145 (6) |
O13 | 0.0317 (6) | 0.0299 (6) | 0.0364 (6) | −0.0036 (5) | 0.0066 (5) | −0.0081 (5) |
O14 | 0.0294 (6) | 0.0523 (8) | 0.0245 (5) | −0.0064 (5) | 0.0043 (4) | 0.0062 (5) |
O15 | 0.0218 (5) | 0.0395 (6) | 0.0291 (6) | 0.0031 (4) | 0.0055 (4) | −0.0048 (5) |
C11 | 0.0217 (9) | 0.0220 (9) | 0.0253 (9) | 0.000 | 0.0058 (7) | 0.000 |
C12 | 0.0219 (6) | 0.0246 (6) | 0.0266 (7) | −0.0028 (5) | 0.0062 (5) | −0.0002 (5) |
C13A | 0.0372 (17) | 0.035 (2) | 0.0257 (17) | −0.002 (2) | 0.0016 (12) | −0.0004 (18) |
C14A | 0.064 (2) | 0.079 (3) | 0.054 (2) | 0.029 (2) | −0.0243 (17) | −0.0062 (19) |
C15A | 0.063 (3) | 0.108 (5) | 0.026 (2) | −0.017 (3) | 0.0141 (17) | −0.007 (3) |
C13B | 0.040 (5) | 0.056 (7) | 0.022 (3) | −0.016 (6) | 0.002 (3) | −0.003 (5) |
C14B | 0.060 (5) | 0.067 (5) | 0.040 (4) | 0.027 (4) | −0.006 (3) | −0.005 (3) |
C15B | 0.204 (18) | 0.040 (5) | 0.023 (5) | 0.010 (7) | −0.013 (6) | −0.003 (3) |
C16 | 0.0264 (7) | 0.0397 (9) | 0.0324 (8) | 0.0063 (6) | 0.0085 (6) | −0.0043 (6) |
C17 | 0.0440 (11) | 0.0479 (11) | 0.0454 (10) | 0.0156 (9) | 0.0077 (8) | 0.0055 (8) |
C18 | 0.0374 (11) | 0.0641 (14) | 0.0657 (15) | 0.0142 (10) | 0.0264 (10) | 0.0232 (11) |
P21 | 0.0373 (2) | 0.02489 (18) | 0.02055 (18) | −0.00273 (15) | 0.00356 (15) | −0.00162 (13) |
S21 | 0.0305 (2) | 0.0330 (2) | 0.02438 (18) | −0.00355 (15) | 0.00056 (14) | 0.00304 (14) |
O21 | 0.0367 (6) | 0.0460 (7) | 0.0303 (6) | 0.0092 (6) | 0.0008 (5) | 0.0067 (5) |
O22 | 0.0445 (8) | 0.0541 (9) | 0.0389 (7) | −0.0219 (7) | 0.0019 (6) | 0.0052 (6) |
O23 | 0.0420 (7) | 0.0285 (6) | 0.0311 (6) | 0.0017 (5) | 0.0007 (5) | −0.0029 (4) |
O24 | 0.0466 (7) | 0.0363 (6) | 0.0292 (6) | −0.0050 (5) | 0.0018 (5) | −0.0085 (5) |
O25 | 0.0428 (7) | 0.0324 (6) | 0.0314 (6) | −0.0025 (5) | 0.0113 (5) | 0.0040 (5) |
C21 | 0.0405 (12) | 0.0239 (9) | 0.0218 (9) | 0.000 | −0.0021 (8) | 0.000 |
C22 | 0.0380 (8) | 0.0272 (7) | 0.0232 (7) | −0.0022 (6) | 0.0043 (6) | −0.0002 (5) |
C23 | 0.0459 (10) | 0.0366 (9) | 0.0361 (9) | −0.0067 (8) | −0.0066 (7) | 0.0008 (7) |
C24 | 0.0525 (13) | 0.0592 (13) | 0.0511 (12) | −0.0067 (11) | 0.0039 (10) | 0.0196 (10) |
C25 | 0.0864 (18) | 0.0602 (15) | 0.0407 (11) | −0.0310 (13) | −0.0218 (11) | 0.0125 (10) |
C26 | 0.0655 (13) | 0.0310 (8) | 0.0402 (10) | −0.0037 (8) | 0.0233 (9) | 0.0055 (7) |
C27 | 0.0712 (17) | 0.0718 (17) | 0.0648 (16) | −0.0309 (14) | 0.0225 (13) | −0.0053 (13) |
C28 | 0.0781 (18) | 0.0714 (17) | 0.0367 (11) | 0.0045 (14) | 0.0095 (11) | 0.0169 (11) |
P31 | 0.0284 (2) | 0.02564 (18) | 0.02487 (19) | 0.00070 (14) | 0.00601 (14) | −0.00023 (13) |
S31 | 0.02421 (18) | 0.03015 (18) | 0.02341 (17) | 0.00079 (13) | 0.00221 (13) | 0.00124 (13) |
O31 | 0.0290 (6) | 0.0402 (6) | 0.0337 (6) | −0.0092 (5) | 0.0046 (4) | −0.0030 (5) |
O32 | 0.0389 (7) | 0.0492 (8) | 0.0324 (6) | 0.0130 (6) | 0.0009 (5) | 0.0106 (6) |
O33 | 0.0403 (7) | 0.0253 (5) | 0.0408 (7) | −0.0026 (5) | 0.0106 (5) | −0.0044 (5) |
O34 | 0.0275 (6) | 0.0364 (6) | 0.0324 (6) | 0.0044 (5) | 0.0027 (4) | −0.0065 (5) |
O35 | 0.0371 (7) | 0.0477 (7) | 0.0260 (6) | 0.0036 (6) | 0.0050 (5) | 0.0080 (5) |
C31 | 0.0299 (10) | 0.0223 (9) | 0.0262 (9) | 0.000 | 0.0078 (8) | 0.000 |
C32 | 0.0277 (7) | 0.0254 (7) | 0.0246 (7) | 0.0004 (5) | 0.0050 (5) | −0.0024 (5) |
C33 | 0.0288 (8) | 0.0432 (10) | 0.0427 (10) | −0.0040 (7) | 0.0009 (7) | −0.0058 (8) |
C34 | 0.0490 (12) | 0.0518 (13) | 0.0599 (14) | 0.0010 (10) | −0.0148 (10) | 0.0068 (10) |
C35 | 0.0319 (11) | 0.143 (3) | 0.0760 (18) | −0.0151 (15) | 0.0172 (11) | −0.024 (2) |
C36A | 0.044 (4) | 0.093 (7) | 0.043 (4) | −0.010 (4) | 0.005 (3) | 0.037 (4) |
C37A | 0.072 (3) | 0.042 (2) | 0.058 (3) | 0.0094 (19) | 0.012 (2) | 0.0191 (19) |
C38A | 0.159 (7) | 0.102 (4) | 0.085 (4) | 0.069 (5) | 0.086 (5) | 0.039 (4) |
C36B | 0.072 (9) | 0.045 (5) | 0.033 (5) | −0.002 (4) | 0.012 (5) | −0.001 (4) |
C37B | 0.108 (8) | 0.077 (6) | 0.025 (3) | 0.023 (5) | 0.008 (4) | −0.009 (3) |
C38B | 0.25 (2) | 0.050 (6) | 0.098 (11) | 0.035 (10) | 0.110 (13) | 0.012 (6) |
P1—O3 | 1.4722 (12) | C17—H17B | 0.9800 |
P1—O5 | 1.5640 (13) | C17—H17C | 0.9800 |
P1—O4 | 1.5693 (12) | C18—H18A | 0.9800 |
P1—C2 | 1.8074 (16) | C18—H18B | 0.9800 |
S1—O2 | 1.4359 (13) | C18—H18C | 0.9800 |
S1—O1 | 1.4407 (13) | P21—O23 | 1.4721 (13) |
S1—C2 | 1.7751 (16) | P21—O25 | 1.5635 (14) |
S1—C1 | 1.7884 (12) | P21—O24 | 1.5658 (13) |
O4—C3A | 1.433 (5) | P21—C22 | 1.8085 (16) |
O4—C3B | 1.520 (6) | S21—O22 | 1.4355 (14) |
O5—C6 | 1.471 (2) | S21—O21 | 1.4394 (13) |
C1—S1i | 1.7884 (12) | S21—C22 | 1.7742 (16) |
C1—H1 | 0.9601 | S21—C21 | 1.7857 (12) |
C2—H2A | 0.9900 | O24—C23 | 1.464 (2) |
C2—H2B | 0.9900 | O25—C26 | 1.465 (2) |
C3A—C5A | 1.505 (6) | C21—S21iii | 1.7857 (12) |
C3A—C4A | 1.519 (6) | C21—H21 | 0.9601 |
C3A—H3A | 1.0000 | C22—H22A | 0.9900 |
C4A—H4AA | 0.9800 | C22—H22B | 0.9900 |
C4A—H4AB | 0.9800 | C23—C24 | 1.501 (3) |
C4A—H4AC | 0.9800 | C23—C25 | 1.512 (3) |
C5A—H5AA | 0.9800 | C23—H23 | 1.0000 |
C5A—H5AB | 0.9800 | C24—H24A | 0.9800 |
C5A—H5AC | 0.9800 | C24—H24B | 0.9800 |
C3B—C5B | 1.484 (8) | C24—H24C | 0.9800 |
C3B—C4B | 1.521 (7) | C25—H25A | 0.9800 |
C3B—H3B | 1.0000 | C25—H25B | 0.9800 |
C4B—H4BA | 0.9800 | C25—H25C | 0.9800 |
C4B—H4BB | 0.9800 | C26—C27 | 1.497 (4) |
C4B—H4BC | 0.9800 | C26—C28 | 1.507 (3) |
C5B—H5BA | 0.9800 | C26—H26 | 1.0000 |
C5B—H5BB | 0.9800 | C27—H27A | 0.9800 |
C5B—H5BC | 0.9800 | C27—H27B | 0.9800 |
C6—C7 | 1.502 (3) | C27—H27C | 0.9800 |
C6—C8 | 1.508 (3) | C28—H28A | 0.9800 |
C6—H6 | 1.0000 | C28—H28B | 0.9800 |
C7—H7A | 0.9800 | C28—H28C | 0.9800 |
C7—H7B | 0.9800 | P31—O33 | 1.4706 (13) |
C7—H7C | 0.9800 | P31—O35 | 1.5629 (13) |
C8—H8A | 0.9800 | P31—O34 | 1.5728 (12) |
C8—H8B | 0.9800 | P31—C32 | 1.8127 (15) |
C8—H8C | 0.9800 | S31—O32 | 1.4355 (13) |
P11—O13 | 1.4729 (12) | S31—O31 | 1.4423 (13) |
P11—O15 | 1.5656 (13) | S31—C32 | 1.7735 (15) |
P11—O14 | 1.5671 (12) | S31—C31 | 1.7879 (12) |
P11—C12 | 1.8058 (15) | O34—C33 | 1.477 (2) |
S11—O12 | 1.4374 (13) | O35—C36B | 1.46 (2) |
S11—O11 | 1.4419 (12) | O35—C36A | 1.473 (10) |
S11—C12 | 1.7740 (14) | C31—S31iv | 1.7879 (12) |
S11—C11 | 1.7929 (11) | C31—H31 | 0.9598 |
O14—C13B | 1.470 (16) | C32—H32A | 0.9900 |
O14—C13A | 1.498 (8) | C32—H32B | 0.9900 |
O15—C16 | 1.4814 (19) | C33—C34 | 1.495 (3) |
C11—S11ii | 1.7929 (11) | C33—C35 | 1.507 (3) |
C11—H11 | 0.9600 | C33—H33 | 1.0000 |
C12—H12A | 0.9900 | C34—H34A | 0.9800 |
C12—H12B | 0.9900 | C34—H34B | 0.9800 |
C13A—C15A | 1.487 (7) | C34—H34C | 0.9800 |
C13A—C14A | 1.505 (7) | C35—H35A | 0.9800 |
C13A—H13A | 1.0000 | C35—H35B | 0.9800 |
C14A—H14A | 0.9800 | C35—H35C | 0.9800 |
C14A—H14B | 0.9800 | C36A—C38A | 1.478 (13) |
C14A—H14C | 0.9800 | C36A—C37A | 1.498 (10) |
C15A—H15A | 0.9800 | C36A—H36A | 1.0000 |
C15A—H15B | 0.9800 | C37A—H37A | 0.9800 |
C15A—H15C | 0.9800 | C37A—H37B | 0.9800 |
C13B—C15B | 1.507 (13) | C37A—H37C | 0.9800 |
C13B—C14B | 1.515 (12) | C38A—H38A | 0.9800 |
C13B—H13B | 1.0000 | C38A—H38B | 0.9800 |
C14B—H14D | 0.9800 | C38A—H38C | 0.9800 |
C14B—H14E | 0.9800 | C36B—C38B | 1.429 (19) |
C14B—H14F | 0.9800 | C36B—C37B | 1.536 (15) |
C15B—H15D | 0.9800 | C36B—H36B | 1.0000 |
C15B—H15E | 0.9800 | C37B—H37D | 0.9800 |
C15B—H15F | 0.9800 | C37B—H37E | 0.9800 |
C16—C17 | 1.499 (3) | C37B—H37F | 0.9800 |
C16—C18 | 1.508 (3) | C38B—H38D | 0.9800 |
C16—H16 | 1.0000 | C38B—H38E | 0.9800 |
C17—H17A | 0.9800 | C38B—H38F | 0.9800 |
O3—P1—O5 | 117.30 (7) | C16—C18—H18C | 109.5 |
O3—P1—O4 | 115.03 (7) | H18A—C18—H18C | 109.5 |
O5—P1—O4 | 103.57 (7) | H18B—C18—H18C | 109.5 |
O3—P1—C2 | 113.86 (7) | O23—P21—O25 | 117.09 (8) |
O5—P1—C2 | 101.31 (7) | O23—P21—O24 | 115.20 (8) |
O4—P1—C2 | 103.95 (7) | O25—P21—O24 | 103.38 (7) |
O2—S1—O1 | 119.43 (8) | O23—P21—C22 | 113.90 (7) |
O2—S1—C2 | 109.54 (8) | O25—P21—C22 | 101.09 (8) |
O1—S1—C2 | 107.34 (8) | O24—P21—C22 | 104.37 (7) |
O2—S1—C1 | 105.49 (9) | O22—S21—O21 | 119.48 (9) |
O1—S1—C1 | 107.82 (7) | O22—S21—C22 | 109.34 (8) |
C2—S1—C1 | 106.54 (6) | O21—S21—C22 | 107.24 (8) |
C3A—O4—P1 | 124.3 (2) | O22—S21—C21 | 105.40 (9) |
C3B—O4—P1 | 120.9 (2) | O21—S21—C21 | 107.91 (7) |
C6—O5—P1 | 122.74 (11) | C22—S21—C21 | 106.84 (6) |
S1i—C1—S1 | 117.41 (12) | C23—O24—P21 | 124.19 (12) |
S1i—C1—H1 | 108.0 | C26—O25—P21 | 122.50 (13) |
S1—C1—H1 | 107.9 | S21iii—C21—S21 | 116.99 (12) |
S1—C2—P1 | 114.63 (9) | S21iii—C21—H21 | 108.1 |
S1—C2—H2A | 108.6 | S21—C21—H21 | 108.0 |
P1—C2—H2A | 108.6 | S21—C22—P21 | 114.42 (9) |
S1—C2—H2B | 108.6 | S21—C22—H22A | 108.7 |
P1—C2—H2B | 108.6 | P21—C22—H22A | 108.7 |
H2A—C2—H2B | 107.6 | S21—C22—H22B | 108.7 |
O4—C3A—C5A | 107.0 (4) | P21—C22—H22B | 108.7 |
O4—C3A—C4A | 106.7 (3) | H22A—C22—H22B | 107.6 |
C5A—C3A—C4A | 110.6 (4) | O24—C23—C24 | 109.23 (17) |
O4—C3A—H3A | 110.8 | O24—C23—C25 | 106.07 (18) |
C5A—C3A—H3A | 110.8 | C24—C23—C25 | 112.17 (18) |
C4A—C3A—H3A | 110.8 | O24—C23—H23 | 109.8 |
C5B—C3B—O4 | 109.7 (5) | C24—C23—H23 | 109.8 |
C5B—C3B—C4B | 114.0 (5) | C25—C23—H23 | 109.8 |
O4—C3B—C4B | 106.2 (4) | C23—C24—H24A | 109.5 |
C5B—C3B—H3B | 109.0 | C23—C24—H24B | 109.5 |
O4—C3B—H3B | 109.0 | H24A—C24—H24B | 109.5 |
C4B—C3B—H3B | 109.0 | C23—C24—H24C | 109.5 |
C3B—C4B—H4BA | 109.5 | H24A—C24—H24C | 109.5 |
C3B—C4B—H4BB | 109.5 | H24B—C24—H24C | 109.5 |
H4BA—C4B—H4BB | 109.5 | C23—C25—H25A | 109.5 |
C3B—C4B—H4BC | 109.5 | C23—C25—H25B | 109.5 |
H4BA—C4B—H4BC | 109.5 | H25A—C25—H25B | 109.5 |
H4BB—C4B—H4BC | 109.5 | C23—C25—H25C | 109.5 |
C3B—C5B—H5BA | 109.5 | H25A—C25—H25C | 109.5 |
C3B—C5B—H5BB | 109.5 | H25B—C25—H25C | 109.5 |
H5BA—C5B—H5BB | 109.5 | O25—C26—C27 | 105.1 (2) |
C3B—C5B—H5BC | 109.5 | O25—C26—C28 | 110.05 (18) |
H5BA—C5B—H5BC | 109.5 | C27—C26—C28 | 113.92 (19) |
H5BB—C5B—H5BC | 109.5 | O25—C26—H26 | 109.2 |
O5—C6—C7 | 105.20 (15) | C27—C26—H26 | 109.2 |
O5—C6—C8 | 109.44 (17) | C28—C26—H26 | 109.2 |
C7—C6—C8 | 113.71 (19) | C26—C27—H27A | 109.5 |
O5—C6—H6 | 109.5 | C26—C27—H27B | 109.5 |
C7—C6—H6 | 109.5 | H27A—C27—H27B | 109.5 |
C8—C6—H6 | 109.5 | C26—C27—H27C | 109.5 |
C6—C7—H7A | 109.5 | H27A—C27—H27C | 109.5 |
C6—C7—H7B | 109.5 | H27B—C27—H27C | 109.5 |
H7A—C7—H7B | 109.5 | C26—C28—H28A | 109.5 |
C6—C7—H7C | 109.5 | C26—C28—H28B | 109.5 |
H7A—C7—H7C | 109.5 | H28A—C28—H28B | 109.5 |
H7B—C7—H7C | 109.5 | C26—C28—H28C | 109.5 |
C6—C8—H8A | 109.5 | H28A—C28—H28C | 109.5 |
C6—C8—H8B | 109.5 | H28B—C28—H28C | 109.5 |
H8A—C8—H8B | 109.5 | O33—P31—O35 | 117.38 (8) |
C6—C8—H8C | 109.5 | O33—P31—O34 | 114.90 (7) |
H8A—C8—H8C | 109.5 | O35—P31—O34 | 102.73 (7) |
H8B—C8—H8C | 109.5 | O33—P31—C32 | 113.16 (7) |
O13—P11—O15 | 117.52 (7) | O35—P31—C32 | 102.53 (7) |
O13—P11—O14 | 114.40 (7) | O34—P31—C32 | 104.49 (7) |
O15—P11—O14 | 103.43 (7) | O32—S31—O31 | 119.12 (8) |
O13—P11—C12 | 112.81 (7) | O32—S31—C32 | 109.16 (8) |
O15—P11—C12 | 102.35 (7) | O31—S31—C32 | 107.16 (8) |
O14—P11—C12 | 104.81 (7) | O32—S31—C31 | 105.98 (9) |
O12—S11—O11 | 119.22 (8) | O31—S31—C31 | 107.85 (7) |
O12—S11—C12 | 109.26 (7) | C32—S31—C31 | 107.01 (6) |
O11—S11—C12 | 107.12 (8) | C33—O34—P31 | 123.92 (11) |
O12—S11—C11 | 105.72 (8) | C36B—O35—P31 | 122.8 (8) |
O11—S11—C11 | 107.88 (6) | C36A—O35—P31 | 118.6 (4) |
C12—S11—C11 | 107.06 (6) | S31—C31—S31iv | 117.09 (12) |
C13B—O14—P11 | 129.3 (6) | S31—C31—H31 | 108.0 |
C13A—O14—P11 | 120.2 (2) | S31iv—C31—H31 | 108.0 |
C16—O15—P11 | 119.94 (11) | S31—C32—P31 | 115.75 (8) |
S11ii—C11—S11 | 116.55 (11) | S31—C32—H32A | 108.3 |
S11ii—C11—H11 | 108.2 | P31—C32—H32A | 108.3 |
S11—C11—H11 | 108.1 | S31—C32—H32B | 108.3 |
S11—C12—P11 | 114.98 (8) | P31—C32—H32B | 108.3 |
S11—C12—H12A | 108.5 | H32A—C32—H32B | 107.4 |
P11—C12—H12A | 108.5 | O34—C33—C34 | 108.60 (16) |
S11—C12—H12B | 108.5 | O34—C33—C35 | 105.06 (18) |
P11—C12—H12B | 108.5 | C34—C33—C35 | 113.9 (2) |
H12A—C12—H12B | 107.5 | O34—C33—H33 | 109.7 |
C15A—C13A—O14 | 107.6 (6) | C34—C33—H33 | 109.7 |
C15A—C13A—C14A | 113.9 (5) | C35—C33—H33 | 109.7 |
O14—C13A—C14A | 104.6 (4) | C33—C34—H34A | 109.5 |
C15A—C13A—H13A | 110.2 | C33—C34—H34B | 109.5 |
O14—C13A—H13A | 110.2 | H34A—C34—H34B | 109.5 |
C14A—C13A—H13A | 110.2 | C33—C34—H34C | 109.5 |
O14—C13B—C15B | 98.0 (11) | H34A—C34—H34C | 109.5 |
O14—C13B—C14B | 115.5 (9) | H34B—C34—H34C | 109.5 |
C15B—C13B—C14B | 108.3 (9) | C33—C35—H35A | 109.5 |
O14—C13B—H13B | 111.4 | C33—C35—H35B | 109.5 |
C15B—C13B—H13B | 111.4 | H35A—C35—H35B | 109.5 |
C14B—C13B—H13B | 111.4 | C33—C35—H35C | 109.5 |
C13B—C14B—H14D | 109.5 | H35A—C35—H35C | 109.5 |
C13B—C14B—H14E | 109.5 | H35B—C35—H35C | 109.5 |
H14D—C14B—H14E | 109.5 | O35—C36A—C38A | 106.8 (8) |
C13B—C14B—H14F | 109.5 | O35—C36A—C37A | 107.3 (7) |
H14D—C14B—H14F | 109.5 | C38A—C36A—C37A | 111.9 (7) |
H14E—C14B—H14F | 109.5 | O35—C36A—H36A | 110.2 |
C13B—C15B—H15D | 109.5 | C38A—C36A—H36A | 110.2 |
C13B—C15B—H15E | 109.5 | C37A—C36A—H36A | 110.2 |
H15D—C15B—H15E | 109.5 | C38B—C36B—O35 | 112.1 (16) |
C13B—C15B—H15F | 109.5 | C38B—C36B—C37B | 112.5 (14) |
H15D—C15B—H15F | 109.5 | O35—C36B—C37B | 111.0 (14) |
H15E—C15B—H15F | 109.5 | C38B—C36B—H36B | 107.0 |
O15—C16—C17 | 107.69 (14) | O35—C36B—H36B | 107.0 |
O15—C16—C18 | 108.01 (15) | C37B—C36B—H36B | 107.0 |
C17—C16—C18 | 112.54 (17) | C36B—C37B—H37D | 109.5 |
O15—C16—H16 | 109.5 | C36B—C37B—H37E | 109.5 |
C17—C16—H16 | 109.5 | H37D—C37B—H37E | 109.5 |
C18—C16—H16 | 109.5 | C36B—C37B—H37F | 109.5 |
C16—C17—H17A | 109.5 | H37D—C37B—H37F | 109.5 |
C16—C17—H17B | 109.5 | H37E—C37B—H37F | 109.5 |
H17A—C17—H17B | 109.5 | C36B—C38B—H38D | 109.5 |
C16—C17—H17C | 109.5 | C36B—C38B—H38E | 109.5 |
H17A—C17—H17C | 109.5 | H38D—C38B—H38E | 109.5 |
H17B—C17—H17C | 109.5 | C36B—C38B—H38F | 109.5 |
C16—C18—H18A | 109.5 | H38D—C38B—H38F | 109.5 |
C16—C18—H18B | 109.5 | H38E—C38B—H38F | 109.5 |
H18A—C18—H18B | 109.5 | ||
O3—P1—O4—C3A | 17.8 (3) | C13A—O14—C13B—C14B | −161 (3) |
O5—P1—O4—C3A | 147.1 (2) | P11—O14—C13B—C14B | 135.4 (7) |
C2—P1—O4—C3A | −107.4 (2) | P11—O15—C16—C17 | −137.88 (14) |
O3—P1—O4—C3B | 44.4 (3) | P11—O15—C16—C18 | 100.33 (17) |
O5—P1—O4—C3B | 173.7 (3) | O23—P21—O24—C23 | 25.61 (16) |
C2—P1—O4—C3B | −80.7 (3) | O25—P21—O24—C23 | 154.60 (14) |
O3—P1—O5—C6 | 32.28 (16) | C22—P21—O24—C23 | −100.03 (14) |
O4—P1—O5—C6 | −95.61 (14) | O23—P21—O25—C26 | 36.62 (17) |
C2—P1—O5—C6 | 156.86 (14) | O24—P21—O25—C26 | −91.20 (15) |
O2—S1—C1—S1i | 176.09 (6) | C22—P21—O25—C26 | 160.95 (14) |
O1—S1—C1—S1i | 47.44 (7) | O22—S21—C21—S21iii | 176.05 (7) |
C2—S1—C1—S1i | −67.53 (6) | O21—S21—C21—S21iii | 47.33 (7) |
O2—S1—C2—P1 | 39.36 (12) | C22—S21—C21—S21iii | −67.70 (6) |
O1—S1—C2—P1 | 170.43 (8) | O22—S21—C22—P21 | 40.73 (13) |
C1—S1—C2—P1 | −74.28 (11) | O21—S21—C22—P21 | 171.65 (9) |
O3—P1—C2—S1 | 42.99 (12) | C21—S21—C22—P21 | −72.86 (11) |
O5—P1—C2—S1 | −83.87 (10) | O23—P21—C22—S21 | 44.75 (12) |
O4—P1—C2—S1 | 168.90 (8) | O25—P21—C22—S21 | −81.72 (10) |
C3B—O4—C3A—C5A | 113.5 (10) | O24—P21—C22—S21 | 171.21 (9) |
P1—O4—C3A—C5A | −157.8 (3) | P21—O24—C23—C24 | 97.35 (18) |
C3B—O4—C3A—C4A | −4.9 (8) | P21—O24—C23—C25 | −141.56 (15) |
P1—O4—C3A—C4A | 83.8 (4) | P21—O25—C26—C27 | −152.51 (16) |
C3A—O4—C3B—C5B | 17.7 (7) | P21—O25—C26—C28 | 84.4 (2) |
P1—O4—C3B—C5B | −88.2 (5) | O33—P31—O34—C33 | 18.92 (16) |
C3A—O4—C3B—C4B | −105.9 (11) | O35—P31—O34—C33 | 147.58 (14) |
P1—O4—C3B—C4B | 148.3 (4) | C32—P31—O34—C33 | −105.67 (14) |
P1—O5—C6—C7 | −151.72 (17) | O33—P31—O35—C36B | 64.7 (10) |
P1—O5—C6—C8 | 85.76 (19) | O34—P31—O35—C36B | −62.3 (10) |
O13—P11—O14—C13B | 33.8 (6) | C32—P31—O35—C36B | −170.6 (10) |
O15—P11—O14—C13B | 162.9 (5) | O33—P31—O35—C36A | 55.6 (6) |
C12—P11—O14—C13B | −90.3 (5) | O34—P31—O35—C36A | −71.5 (6) |
O13—P11—O14—C13A | 16.2 (3) | C32—P31—O35—C36A | −179.7 (6) |
O15—P11—O14—C13A | 145.3 (3) | O32—S31—C31—S31iv | 174.83 (6) |
C12—P11—O14—C13A | −107.9 (3) | O31—S31—C31—S31iv | 46.22 (6) |
O13—P11—O15—C16 | 57.69 (14) | C32—S31—C31—S31iv | −68.78 (6) |
O14—P11—O15—C16 | −69.41 (13) | O32—S31—C32—P31 | 45.23 (12) |
C12—P11—O15—C16 | −178.15 (12) | O31—S31—C32—P31 | 175.50 (8) |
O12—S11—C11—S11ii | 175.24 (6) | C31—S31—C32—P31 | −69.04 (10) |
O11—S11—C11—S11ii | 46.65 (6) | O33—P31—C32—S31 | 41.17 (12) |
C12—S11—C11—S11ii | −68.35 (6) | O35—P31—C32—S31 | −86.24 (10) |
O12—S11—C12—P11 | 42.73 (11) | O34—P31—C32—S31 | 166.86 (8) |
O11—S11—C12—P11 | 173.17 (8) | P31—O34—C33—C34 | 97.55 (18) |
C11—S11—C12—P11 | −71.32 (10) | P31—O34—C33—C35 | −140.2 (2) |
O13—P11—C12—S11 | 41.33 (11) | C36B—O35—C36A—C38A | −10 (8) |
O15—P11—C12—S11 | −85.91 (9) | P31—O35—C36A—C38A | 110.2 (6) |
O14—P11—C12—S11 | 166.40 (8) | C36B—O35—C36A—C37A | 110 (8) |
C13B—O14—C13A—C15A | 95 (3) | P31—O35—C36A—C37A | −129.6 (5) |
P11—O14—C13A—C15A | −137.8 (4) | C36A—O35—C36B—C38B | −26 (7) |
C13B—O14—C13A—C14A | −26 (2) | P31—O35—C36B—C38B | −90.2 (18) |
P11—O14—C13A—C14A | 100.7 (4) | C36A—O35—C36B—C37B | −153 (10) |
C13A—O14—C13B—C15B | −47 (2) | P31—O35—C36B—C37B | 143.0 (10) |
P11—O14—C13B—C15B | −109.8 (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 formula | C15H34O10P2S2 |
Mr | 500.50 |
Crystal system, space group | Monoclinic, P2/n |
Temperature (K) | 180 |
a, b, c (Å) | 21.7314 (17), 10.2307 (8), 21.8150 (17) |
β (°) | 92.922 (5) |
V (Å3) | 4843.8 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.40 × 0.25 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART APEX II |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2005) |
Tmin, Tmax | 0.857, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 53365, 14085, 12471 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.117, 1.08 |
No. of reflections | 14085 |
No. of parameters | 627 |
No. of restraints | 9 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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.
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]°.