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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Jun 9;66(Pt 7):o1615–o1616. doi: 10.1107/S1600536810020362

3′,4′-Dichloro­biphenyl-4-yl 2,2,2-trichloro­ethyl sulfate

Xueshu Li a, Sean Parkin b, Michael W Duffel c, Larry W Robertson a, Hans-Joachim Lehmler a,*
PMCID: PMC3006693  PMID: 21587847

Abstract

The four independent mol­ecules in the asymmetric unit of the title compound, C14H9Cl5O4S, are related by pseudo-inversion centres. The mol­ecules have Caromatic—O bond lengths ranging from 1.426 (10) to 1.449 (9) Å and biphenyl-4-yl sulfate ester bond lengths ranging from 1.563 (6) to 1.586 (6) Å, which is comparable to structurally related sulfuric acid diesters. The dihedral angles between the benzene rings range from 22.5 (4) to 29.1 (4)° and are significantly smaller than the calculated dihedral angle of 41.2°.

Related literature

For the structures of similar sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ethyl esters, see: Li et al. (2008 ▶, 2010a ▶,b ▶). For a review of the structures of sulfuric acid aryl mono esters, see: Brandao et al. (2005 ▶). For further discussion of dihedral angles in chlorinated biphenyl derivatives, see: Lehmler et al. (2002 ▶); Shaikh et al. (2008 ▶); Vyas et al. (2006 ▶). For additional background on polychlorinated biphenyls, see: Letcher et al. (2000 ▶); Robertson & Hansen (2001 ▶); Liu et al. (2004a ▶,b ▶); Liu et al. (2006 ▶, 2009 ▶); Sacco & James (2005 ▶); Tampal et al. (2002 ▶). For software used to caculate dihedral angles, see: Carpenter et al. (1980 ▶).graphic file with name e-66-o1615-scheme1.jpg

Experimental

Crystal data

  • C14H9Cl5O4S

  • M r = 450.52

  • Monoclinic, Inline graphic

  • a = 7.2491 (1) Å

  • b = 40.5988 (7) Å

  • c = 12.1145 (2) Å

  • β = 106.1551 (7)°

  • V = 3424.57 (9) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.99 mm−1

  • T = 90 K

  • 0.40 × 0.34 × 0.18 mm

Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.658, T max = 0.843

  • 44794 measured reflections

  • 14652 independent reflections

  • 8149 reflections with I > 2σ(I)

  • R int = 0.110

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062

  • wR(F 2) = 0.156

  • S = 1.00

  • 14652 reflections

  • 769 parameters

  • 249 restraints

  • H-atom parameters constrained

  • Δρmax = 1.11 e Å−3

  • Δρmin = −0.59 e Å−3

  • Absolute structure: Flack (1983 ▶), 6676 Friedel pairs

  • Flack parameter: 0.10 (9)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020362/lh5052sup1.cif

e-66-o1615-sup1.cif (42.9KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020362/lh5052Isup2.hkl

e-66-o1615-Isup2.hkl (716.1KB, hkl)

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

Acknowledgments

This research was supported by grants ES05605, ES013661 and ES017425 from the National Institute of Environmental Health Sciences, NIH.

supplementary crystallographic information

Comment

Hydroxylated polychlorinated biphenyls (PCBs) are an important class of metabolites of PCBs (Letcher et al., 2000) that can be further metabolized to PCB glucuronides (Tampal et al., 2002) or sulfates (Liu et al., 2006; Liu et al., 2009; Sacco & James, 2005). The chemical structure and toxicity of these glucuronide and sulfate metabolites are only poorly investigated, in part because authentic standards are not readily available or because of their limited chemical stability. Here we report the crystal structure of a 2,2,2-trichloroethyl-protected sulfate of 3',4'-dichloro-biphenyl-4-ol, an intermediate of the synthesis of the corresponding sulfate monoester.

The CAr—O (i.e. O1—C4) bond lengths of the title compound are 1.431 (10) Å (O1A—C4A), 1.426 (10) Å (O1B—C4B), 1.427 (10) Å (O1C—C4C) and 1.449 (9) Å (O1D—C4D), respectively. In related sulfuric acid diesters without chlorine substituents in the sulfated phenyl ring, the analogous CAr—O bond lengths were comparable and ranged from 1.426 (2) to 1.435 (5) Å (Li et al., 2010a,b; Li et al., 2008). A much shorter CAr—O bond length was observed in 2',3,5',5-tetrachloro-biphenyl-4-yl 2,2,2-trichloroethyl sulfate with 1.405 (4) Å (Li et al., 2010b). Similar to sulfate monoesters (Brandao et al., 2005), the differences in the CAr—O bond lengths of the sulfate diesters are due to a more positive partial charge on the C4 carbon atom in the presence of chlorine substituents, which results in a shorter CAr—O bond length.

The biphenyl-4-yl sulfate ester (i.e. S1—O1) bond lengths of the title compound were 1.571 (6) Å (S1A—O1A), 1.584 (6) Å (S1B—O1B), 1.586 (6) Å (S1C—O1C) and 1.563 (6) Å (S1D—O1D), respectively. These bond lengths are also comparable to related sulfuric acid diesters (Li et al., 2010a,b; Li et al., 2008), but shorter compared to 2',3,5',5-tetrachloro-biphenyl-4-yl 2,2,2-trichloroethyl sulfate, a sulfuric acid diester with two chlorine substituents in the sulfated phenyl ring (Li et al., 2010b). The differences in the biphenyl-4-yl sulfate ester bond lengths are also a due to the presence or absence of electron withdrawing chlorine substituents, which reduce the electron density on the oxygen atom and contribute to a longer and weaker bond in sulfate mono- and diesters with chlorine substituents in the sulfated phenyl ring (Brandao et al., 2005; Li et al., 2010b).

The four molecules in the asymmetyric unit are related by a pseudo-inversion center at (0.75056, 0.50005, 0.62549). Molecules with the A & B atom label suffixes are further related by a pseudo-inversion at (0.23935, 0.50071, 0.37554), while molecules C & D are related by a pseudo-inversion at (1.26176, 0.49939, 0.87544).

The dihedral angle Ar—Ar' between the phenyl rings of a PCB derivative determines its three dimensional structure and, thus, its affinity to cellular targets (Lehmler et al., 2002; Shaikh et al., 2008; Vyas et al., 2006). The solid state dihedral angles between the two phenyl rings of the title compound were 27.2 (4)°, 23.5 (4)°, 29.1 (4)° and 22.5 (4)°, respectively. The corresponding solid state dihedral angles of other sulfate diesters without ortho chlorine substituents range from 4.9 to 41.8° (Li et al., 2010a; Li et al., 2008). Typically, the dihedral angles of such sulfate diester derivatives are smaller than the calculated dihedral angle of 41.2° (calculated using semi-empirical SCF-MO calculations with an Austin Model 1 (AM1) Hamiltonian as implemented by the Spartan 02 package [Carpenter et al., 1980]). These deviations from the calculated dihedral angles are likely due to crystal packing effects, which allow the sulfate diester molecule to adopt an energetically unfavorable dihedral angle to maximize intermolecular interactions in the crystal. Overall, the differences between solid state and calculated dihedral angles indicate that the biphenyl moiety of biphenyl-4-yl sulfate ester has considerable conformational freedom in interacting with cellular target molecules.

Experimental

The title compound was synthesized from 3',4'-dichloro-biphenyl-4-ol by sulfation with 2,2,2-trichloroethyl sulfonyl chloride using 4-dimethylaminopyridine as catalyst (Li et al., 2008; Liu et al. 2004a,b). Crystals suitable for crystal structure analysis were obtained by slowly evaporating a methanolic solution of the title compound.

Refinement

H atoms were found in difference Fourier maps and subsequently placed in idealized positions with constrained C—H distances of 0.99 Å (CH2), and 0.95 Å (CArH) with Uiso(H) values set to 1.2Ueq of the attached atom.

Figures

Fig. 1.

Fig. 1.

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View of one of the four independent molecules of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C14H9Cl5O4S F(000) = 1808
Mr = 450.52 Dx = 1.748 Mg m−3
Monoclinic, P21 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb Cell parameters from 47065 reflections
a = 7.2491 (1) Å θ = 1.0–27.5°
b = 40.5988 (7) Å µ = 0.99 mm−1
c = 12.1145 (2) Å T = 90 K
β = 106.1551 (7)° Block, colourless
V = 3424.57 (9) Å3 0.40 × 0.34 × 0.18 mm
Z = 8
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Data collection

Nonius KappaCCD diffractometer 14652 independent reflections
Radiation source: fine-focus sealed tube 8149 reflections with I > 2σ(I)
graphite Rint = 0.110
Detector resolution: 18 pixels mm-1 θmax = 27.5°, θmin = 1.8°
ω scans at fixed χ = 55° h = −9→9
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) k = −52→52
Tmin = 0.658, Tmax = 0.843 l = 0→15
44794 measured reflections
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Refinement

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)] = 0.062 H-atom parameters constrained
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.0685P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00 (Δ/σ)max = 0.001
14652 reflections Δρmax = 1.11 e Å−3
769 parameters Δρmin = −0.59 e Å−3
249 restraints Absolute structure: Flack (1983), 6676 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.10 (9)
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Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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 > 2σ(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.There is a pseudo inversion at (0.75070 0.50000 0.62576), but it does seem as if the space group really is P21. This came as a great surprise because there seems to be no obvious reason why this structure would be non-centrosymmetric. All indications are that the crystals themselves are non even inversion twins because the Flack (and Hooft 'y') parameters are both zero within a couple of SUs. Although these SUs are a bit larger than the recommendation suggested by Flack. Further tests with various procedures in PLATON (including ADDSYM) suggest "No Obvious Spacegroup Change Needed/Suggested", but the checkCIF implementation of ADDSYM does suggest "ADDSYM Detects Additional (Pseudo) Symm. Elem··· m", but on inspection the structure does not seem to have any kind of mirror plane. Further, the checkCIF implementation of ADDSYM/MISSYM suggests "Potential lattice centering or halving", but again, on inspection of the model and the diffraction data this does not appear to be the case.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
S1A 0.0897 (3) 0.41379 (5) 0.3801 (2) 0.0212 (6)
O1A 0.2072 (8) 0.38089 (14) 0.4093 (5) 0.0201 (14)
O2A 0.2419 (9) 0.44128 (15) 0.4286 (6) 0.0215 (14)
O3A 0.0317 (9) 0.41873 (16) 0.2587 (6) 0.0263 (15)
O4A −0.0441 (8) 0.41263 (15) 0.4467 (6) 0.0284 (16)
Cl1A 0.5435 (3) 0.24939 (5) −0.10621 (17) 0.0304 (5)
Cl2A 0.8863 (3) 0.28876 (5) −0.1569 (2) 0.0305 (6)
Cl3A 0.4320 (3) 0.50544 (5) 0.5117 (2) 0.0244 (6)
Cl4A 0.5427 (3) 0.47314 (5) 0.7332 (2) 0.0261 (6)
Cl5A 0.6711 (3) 0.44744 (5) 0.5439 (2) 0.0227 (6)
C1A 0.4851 (13) 0.3429 (2) 0.1757 (9) 0.0197 (19)
C2A 0.5790 (11) 0.36492 (19) 0.2620 (7) 0.023 (2)
H2A 0.7079 0.3711 0.2681 0.027*
C3A 0.4877 (12) 0.37792 (19) 0.3385 (7) 0.0238 (19)
H3A 0.5529 0.3928 0.3969 0.029*
C4A 0.3030 (13) 0.3690 (2) 0.3287 (8) 0.020 (2)
C5A 0.2038 (12) 0.34682 (18) 0.2459 (7) 0.0267 (19)
H5A 0.0751 0.3408 0.2410 0.032*
C6A 0.2961 (11) 0.33403 (19) 0.1724 (7) 0.0230 (18)
H6A 0.2305 0.3185 0.1165 0.028*
C7A 0.3002 (12) 0.44536 (19) 0.5532 (8) 0.0217 (10)
H7A1 0.3292 0.4237 0.5915 0.026*
H7A2 0.1960 0.4559 0.5788 0.026*
C8A 0.4790 (12) 0.46710 (18) 0.5830 (8) 0.0180 (10)
C1'A 0.5824 (11) 0.32855 (19) 0.0935 (8) 0.0194 (10)
C2'A 0.5326 (11) 0.29847 (19) 0.0421 (6) 0.0220 (10)
H2'A 0.4350 0.2859 0.0609 0.026*
C3'A 0.6208 (11) 0.28622 (17) −0.0356 (6) 0.0191 (9)
C4'A 0.7679 (10) 0.30432 (19) −0.0626 (7) 0.0207 (10)
C5'A 0.8189 (10) 0.33416 (18) −0.0107 (7) 0.0239 (11)
H5'A 0.9202 0.3463 −0.0270 0.029*
C6'A 0.7259 (10) 0.34709 (18) 0.0654 (7) 0.0222 (11)
H6'A 0.7591 0.3683 0.0981 0.027*
S1B 0.4062 (3) 0.59117 (5) 0.3690 (2) 0.0230 (6)
O1B 0.2827 (8) 0.62391 (15) 0.3453 (5) 0.0212 (14)
O2B 0.2532 (9) 0.56336 (14) 0.3155 (6) 0.0197 (14)
O3B 0.4676 (9) 0.58420 (16) 0.4878 (6) 0.0292 (16)
O4B 0.5361 (9) 0.59447 (15) 0.3028 (6) 0.0271 (16)
Cl1B −0.0381 (3) 0.73774 (5) 0.90518 (18) 0.0349 (6)
Cl2B −0.4422 (3) 0.70796 (5) 0.9015 (2) 0.0340 (6)
Cl3B 0.0707 (3) 0.49999 (5) 0.2225 (2) 0.0258 (6)
Cl4B −0.0582 (4) 0.53617 (6) 0.0088 (2) 0.0300 (6)
Cl5B −0.1718 (3) 0.55696 (6) 0.2089 (2) 0.0275 (6)
C1B −0.0147 (13) 0.6568 (2) 0.5751 (9) 0.0200 (19)
C2B −0.0462 (11) 0.62525 (19) 0.5291 (7) 0.0215 (19)
H2B −0.1336 0.6112 0.5523 0.026*
C3B 0.0429 (12) 0.6137 (2) 0.4523 (7) 0.025 (2)
H3B 0.0134 0.5926 0.4183 0.030*
C4B 0.1814 (13) 0.6343 (2) 0.4246 (8) 0.0186 (19)
C5B 0.2204 (12) 0.66517 (18) 0.4713 (7) 0.025 (2)
H5B 0.3160 0.6785 0.4536 0.030*
C6B 0.1199 (10) 0.67649 (19) 0.5436 (7) 0.0224 (19)
H6B 0.1422 0.6983 0.5731 0.027*
C7B 0.1908 (12) 0.56185 (19) 0.1911 (8) 0.0216 (10)
H7B1 0.2934 0.5527 0.1608 0.026*
H7B2 0.1566 0.5841 0.1580 0.026*
C8B 0.0133 (13) 0.53908 (19) 0.1617 (8) 0.0214 (10)
C1'B −0.1193 (11) 0.66870 (19) 0.6604 (8) 0.0186 (10)
C2'B −0.0398 (11) 0.69443 (17) 0.7376 (6) 0.0211 (10)
H2'B 0.0813 0.7036 0.7387 0.025*
C3'B −0.1394 (12) 0.70619 (17) 0.8115 (7) 0.0217 (10)
C4'B −0.3189 (11) 0.6936 (2) 0.8076 (7) 0.0230 (11)
C5'B −0.3956 (11) 0.66792 (19) 0.7326 (7) 0.0264 (11)
H5'B −0.5161 0.6586 0.7321 0.032*
C6'B −0.2966 (10) 0.65610 (18) 0.6594 (7) 0.0224 (11)
H6'B −0.3511 0.6390 0.6072 0.027*
S1C 1.3915 (3) 0.58721 (5) 0.8798 (2) 0.0214 (6)
O1C 1.2647 (9) 0.61955 (15) 0.8500 (5) 0.0242 (15)
O2C 1.2418 (8) 0.55900 (14) 0.8285 (6) 0.0177 (13)
O3C 1.4484 (9) 0.58174 (15) 0.9986 (6) 0.0258 (15)
O4C 1.5231 (9) 0.58960 (16) 0.8136 (6) 0.0276 (16)
Cl1C 0.9555 (3) 0.75553 (5) 1.35532 (17) 0.0298 (5)
Cl2C 0.6170 (3) 0.71937 (5) 1.4213 (2) 0.0291 (6)
Cl3C 1.0490 (3) 0.49568 (5) 0.7412 (2) 0.0263 (6)
Cl4C 0.9415 (3) 0.52908 (6) 0.5218 (2) 0.0272 (6)
Cl5C 0.8154 (3) 0.55435 (5) 0.7123 (2) 0.0234 (6)
C1C 0.9952 (13) 0.6580 (2) 1.0860 (8) 0.0180 (18)
C2C 0.8978 (12) 0.6360 (2) 1.0020 (7) 0.0213 (19)
H2C 0.7686 0.6302 0.9967 0.026*
C3C 0.9883 (11) 0.6224 (2) 0.9259 (8) 0.021 (2)
H3C 0.9225 0.6070 0.8695 0.025*
C4C 1.1745 (13) 0.6314 (2) 0.9331 (9) 0.020 (2)
C5C 1.2746 (11) 0.65297 (18) 1.0156 (7) 0.0226 (19)
H5C 1.4025 0.6591 1.0189 0.027*
C6C 1.1847 (11) 0.66571 (18) 1.0941 (7) 0.0245 (19)
H6C 1.2542 0.6798 1.1539 0.029*
C7C 1.1868 (12) 0.55543 (19) 0.7048 (8) 0.0217 (10)
H7C1 1.2900 0.5444 0.6795 0.026*
H7C2 1.1613 0.5772 0.6671 0.026*
C8C 1.0047 (12) 0.53442 (19) 0.6746 (8) 0.0180 (10)
C1'C 0.9007 (11) 0.6729 (2) 1.1687 (8) 0.0194 (10)
C2'C 0.9571 (11) 0.70446 (18) 1.2150 (7) 0.0220 (10)
H2'C 1.0530 0.7163 1.1920 0.026*
C3'C 0.8720 (11) 0.71828 (17) 1.2947 (7) 0.0191 (9)
C4'C 0.7265 (10) 0.70184 (19) 1.3256 (7) 0.0207 (10)
C5'C 0.6697 (10) 0.67109 (18) 1.2808 (7) 0.0239 (11)
H5'C 0.5705 0.6597 1.3022 0.029*
C6'C 0.7582 (10) 0.65668 (18) 1.2039 (6) 0.0222 (11)
H6'C 0.7198 0.6353 1.1749 0.027*
S1D 1.1226 (3) 0.40890 (5) 0.8723 (2) 0.0231 (6)
O1D 1.2492 (9) 0.37714 (14) 0.8970 (6) 0.0249 (15)
O2D 1.2695 (9) 0.43669 (15) 0.9271 (6) 0.0236 (14)
O3D 1.0666 (9) 0.41554 (16) 0.7527 (6) 0.0258 (15)
O4D 0.9884 (9) 0.40510 (15) 0.9376 (6) 0.0302 (17)
Cl1D 1.5275 (3) 0.25787 (5) 0.33982 (19) 0.0384 (6)
Cl2D 1.9395 (4) 0.28238 (6) 0.3372 (2) 0.0377 (6)
Cl3D 1.4471 (3) 0.50056 (6) 1.0258 (2) 0.0277 (6)
Cl4D 1.5717 (4) 0.46324 (6) 1.2378 (2) 0.0313 (6)
Cl5D 1.6925 (3) 0.44383 (6) 1.0375 (2) 0.0271 (6)
C1D 1.5371 (12) 0.3415 (2) 0.6623 (8) 0.0188 (19)
C2D 1.5793 (11) 0.3726 (2) 0.7139 (7) 0.0188 (18)
H2D 1.6748 0.3858 0.6954 0.023*
C3D 1.4871 (12) 0.3845 (2) 0.7900 (7) 0.025 (2)
H3D 1.5191 0.4056 0.8244 0.030*
C4D 1.3491 (13) 0.3658 (2) 0.8158 (8) 0.020 (2)
C5D 1.3035 (10) 0.33494 (18) 0.7725 (7) 0.0214 (18)
H5D 1.2096 0.3221 0.7941 0.026*
C6D 1.3979 (11) 0.32293 (19) 0.6966 (7) 0.0242 (19)
H6D 1.3680 0.3014 0.6662 0.029*
C7D 1.3283 (12) 0.43822 (19) 1.0533 (8) 0.0216 (10)
H7D1 1.3613 0.4160 1.0866 0.026*
H7D2 1.2240 0.4474 1.0820 0.026*
C8D 1.5031 (13) 0.4606 (2) 1.0844 (8) 0.0214 (10)
C1'D 1.6335 (11) 0.32815 (19) 0.5800 (8) 0.0186 (10)
C2'D 1.5501 (11) 0.30334 (18) 0.5052 (6) 0.0211 (10)
H2'D 1.4264 0.2956 0.5052 0.025*
C3'D 1.6406 (12) 0.28921 (18) 0.4299 (7) 0.0217 (10)
C4'D 1.8203 (11) 0.30051 (19) 0.4282 (7) 0.0230 (11)
C5'D 1.9067 (11) 0.32561 (18) 0.5010 (7) 0.0264 (11)
H5'D 2.0292 0.3336 0.4995 0.032*
C6'D 1.8147 (10) 0.33916 (18) 0.5761 (6) 0.0224 (11)
H6'D 1.8759 0.3563 0.6263 0.027*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1A 0.0144 (12) 0.0222 (12) 0.0243 (15) 0.0009 (9) 0.0012 (11) −0.0047 (10)
O1A 0.022 (3) 0.018 (3) 0.019 (4) 0.003 (2) 0.005 (3) −0.001 (2)
O2A 0.019 (3) 0.025 (3) 0.017 (3) −0.004 (2) −0.001 (3) −0.003 (3)
O3A 0.022 (4) 0.033 (4) 0.019 (3) 0.009 (3) −0.003 (3) −0.007 (3)
O4A 0.016 (3) 0.037 (4) 0.035 (4) −0.001 (3) 0.011 (3) −0.014 (3)
Cl1A 0.0348 (13) 0.0293 (12) 0.0293 (13) −0.0069 (9) 0.0126 (10) −0.0087 (10)
Cl2A 0.0346 (13) 0.0305 (12) 0.0323 (13) 0.0078 (9) 0.0188 (11) 0.0069 (10)
Cl3A 0.0275 (13) 0.0194 (11) 0.0251 (14) 0.0000 (9) 0.0055 (10) 0.0018 (10)
Cl4A 0.0261 (13) 0.0303 (13) 0.0211 (13) −0.0051 (9) 0.0055 (10) −0.0025 (10)
Cl5A 0.0165 (12) 0.0257 (12) 0.0257 (15) 0.0004 (9) 0.0056 (11) −0.0017 (10)
C1A 0.020 (5) 0.012 (4) 0.026 (5) 0.004 (3) 0.005 (4) −0.001 (3)
C2A 0.015 (4) 0.023 (4) 0.028 (5) −0.006 (3) 0.002 (4) −0.001 (4)
C3A 0.032 (4) 0.013 (4) 0.025 (5) −0.001 (3) 0.005 (4) 0.000 (3)
C4A 0.023 (5) 0.019 (4) 0.017 (5) 0.009 (3) 0.006 (4) 0.005 (3)
C5A 0.023 (4) 0.019 (4) 0.037 (5) 0.000 (3) 0.005 (4) 0.001 (4)
C6A 0.023 (4) 0.022 (4) 0.020 (5) −0.004 (3) 0.000 (4) 0.000 (3)
C7A 0.022 (2) 0.021 (2) 0.020 (2) −0.0052 (18) 0.0028 (19) −0.0055 (19)
C8A 0.011 (2) 0.022 (2) 0.019 (2) −0.0015 (17) 0.0019 (18) −0.0006 (18)
C1'A 0.015 (2) 0.020 (2) 0.022 (3) 0.0018 (18) 0.0032 (19) 0.0026 (18)
C2'A 0.020 (2) 0.022 (2) 0.026 (3) 0.0031 (19) 0.009 (2) 0.0043 (19)
C3'A 0.021 (2) 0.015 (2) 0.018 (2) −0.0054 (18) 0.0011 (18) −0.0016 (18)
C4'A 0.020 (2) 0.017 (2) 0.028 (3) 0.0067 (18) 0.011 (2) 0.004 (2)
C5'A 0.020 (3) 0.020 (2) 0.033 (3) 0.0026 (19) 0.011 (2) 0.010 (2)
C6'A 0.023 (3) 0.017 (2) 0.025 (3) −0.0019 (19) 0.004 (2) 0.002 (2)
S1B 0.0190 (13) 0.0205 (11) 0.0275 (15) −0.0011 (9) 0.0034 (11) −0.0024 (10)
O1B 0.023 (3) 0.021 (3) 0.019 (4) 0.001 (2) 0.004 (3) 0.000 (3)
O2B 0.023 (3) 0.019 (3) 0.014 (3) −0.006 (2) 0.001 (3) −0.001 (3)
O3B 0.030 (4) 0.027 (4) 0.024 (4) 0.001 (3) −0.003 (3) 0.001 (3)
O4B 0.019 (3) 0.021 (3) 0.043 (4) −0.006 (2) 0.012 (3) −0.008 (3)
Cl1B 0.0393 (13) 0.0315 (12) 0.0332 (14) −0.0022 (10) 0.0089 (11) −0.0108 (10)
Cl2B 0.0449 (15) 0.0324 (12) 0.0309 (14) 0.0079 (10) 0.0208 (11) 0.0038 (11)
Cl3B 0.0262 (13) 0.0218 (11) 0.0287 (14) −0.0015 (9) 0.0061 (10) 0.0000 (10)
Cl4B 0.0325 (14) 0.0342 (13) 0.0203 (13) −0.0054 (10) 0.0024 (11) −0.0041 (10)
Cl5B 0.0193 (13) 0.0335 (13) 0.0289 (16) 0.0020 (10) 0.0052 (11) −0.0034 (11)
C1B 0.017 (4) 0.024 (4) 0.017 (5) 0.003 (3) 0.002 (4) 0.007 (3)
C2B 0.014 (4) 0.022 (4) 0.028 (5) −0.004 (3) 0.006 (4) 0.000 (4)
C3B 0.036 (5) 0.017 (4) 0.021 (5) −0.001 (3) 0.008 (4) −0.001 (4)
C4B 0.022 (5) 0.018 (4) 0.017 (5) 0.006 (3) 0.007 (4) 0.003 (3)
C5B 0.033 (5) 0.018 (4) 0.026 (5) −0.006 (3) 0.010 (4) 0.002 (4)
C6B 0.022 (5) 0.017 (4) 0.024 (5) −0.003 (3) 0.001 (4) −0.004 (4)
C7B 0.023 (3) 0.023 (2) 0.018 (2) −0.0027 (19) 0.0032 (19) 0.0011 (19)
C8B 0.020 (3) 0.023 (2) 0.020 (2) 0.0023 (18) 0.004 (2) −0.0017 (19)
C1'B 0.015 (2) 0.017 (2) 0.021 (3) 0.0037 (18) 0.0005 (18) 0.0009 (18)
C2'B 0.023 (2) 0.015 (2) 0.024 (3) −0.0031 (18) 0.005 (2) 0.0013 (18)
C3'B 0.028 (3) 0.015 (2) 0.020 (3) 0.0018 (19) 0.005 (2) 0.0003 (19)
C4'B 0.026 (3) 0.025 (3) 0.018 (3) 0.009 (2) 0.006 (2) 0.005 (2)
C5'B 0.023 (3) 0.029 (3) 0.027 (3) 0.001 (2) 0.007 (2) 0.009 (2)
C6'B 0.021 (2) 0.021 (3) 0.022 (3) −0.004 (2) 0.002 (2) 0.000 (2)
S1C 0.0168 (12) 0.0220 (12) 0.0247 (15) −0.0005 (9) 0.0047 (11) −0.0026 (10)
O1C 0.026 (3) 0.024 (3) 0.022 (4) 0.006 (2) 0.005 (3) −0.002 (3)
O2C 0.015 (3) 0.020 (3) 0.017 (3) 0.000 (2) 0.004 (3) 0.001 (3)
O3C 0.024 (4) 0.024 (3) 0.023 (3) 0.000 (3) −0.004 (3) −0.004 (3)
O4C 0.019 (3) 0.034 (4) 0.034 (4) −0.006 (3) 0.014 (3) −0.004 (3)
Cl1C 0.0302 (12) 0.0263 (11) 0.0381 (14) −0.0078 (9) 0.0179 (11) −0.0122 (10)
Cl2C 0.0332 (13) 0.0271 (11) 0.0329 (14) 0.0021 (9) 0.0191 (11) 0.0018 (10)
Cl3C 0.0246 (13) 0.0213 (11) 0.0334 (15) −0.0017 (9) 0.0086 (11) −0.0008 (10)
Cl4C 0.0261 (13) 0.0366 (14) 0.0185 (13) −0.0075 (10) 0.0055 (10) −0.0055 (10)
Cl5C 0.0182 (13) 0.0247 (12) 0.0269 (15) 0.0012 (9) 0.0056 (11) −0.0010 (11)
C1C 0.015 (4) 0.022 (4) 0.014 (5) 0.003 (3) −0.001 (3) 0.007 (3)
C2C 0.015 (4) 0.024 (4) 0.023 (5) −0.001 (3) 0.002 (4) −0.001 (3)
C3C 0.010 (4) 0.023 (4) 0.030 (5) −0.003 (3) 0.004 (4) −0.007 (4)
C4C 0.021 (4) 0.016 (4) 0.026 (5) −0.001 (3) 0.012 (4) 0.001 (3)
C5C 0.014 (4) 0.020 (4) 0.032 (5) −0.003 (3) 0.003 (4) −0.008 (4)
C6C 0.025 (4) 0.023 (4) 0.028 (5) −0.001 (3) 0.012 (4) −0.002 (4)
C7C 0.022 (2) 0.021 (2) 0.020 (2) −0.0052 (18) 0.0028 (19) −0.0055 (19)
C8C 0.011 (2) 0.022 (2) 0.019 (2) −0.0015 (17) 0.0019 (18) −0.0006 (18)
C1'C 0.015 (2) 0.020 (2) 0.022 (3) 0.0018 (18) 0.0032 (19) 0.0026 (18)
C2'C 0.020 (2) 0.022 (2) 0.026 (3) 0.0031 (19) 0.009 (2) 0.0043 (19)
C3'C 0.021 (2) 0.015 (2) 0.018 (2) −0.0054 (18) 0.0011 (18) −0.0016 (18)
C4'C 0.020 (2) 0.017 (2) 0.028 (3) 0.0067 (18) 0.011 (2) 0.004 (2)
C5'C 0.020 (3) 0.020 (2) 0.033 (3) 0.0026 (19) 0.011 (2) 0.010 (2)
C6'C 0.023 (3) 0.017 (2) 0.025 (3) −0.0019 (19) 0.004 (2) 0.002 (2)
S1D 0.0183 (12) 0.0207 (11) 0.0268 (15) −0.0013 (9) 0.0003 (11) −0.0027 (10)
O1D 0.035 (4) 0.018 (3) 0.026 (4) 0.003 (2) 0.016 (3) 0.000 (3)
O2D 0.024 (3) 0.028 (3) 0.017 (3) −0.003 (2) 0.002 (3) −0.004 (3)
O3D 0.020 (3) 0.030 (4) 0.022 (3) 0.004 (3) −0.002 (3) 0.000 (3)
O4D 0.025 (4) 0.033 (4) 0.035 (4) −0.001 (3) 0.012 (3) 0.000 (3)
Cl1D 0.0458 (14) 0.0328 (13) 0.0382 (15) −0.0103 (10) 0.0146 (12) −0.0116 (11)
Cl2D 0.0480 (15) 0.0372 (13) 0.0348 (14) 0.0042 (11) 0.0231 (12) 0.0000 (11)
Cl3D 0.0303 (13) 0.0209 (11) 0.0291 (14) 0.0023 (9) 0.0038 (11) −0.0007 (10)
Cl4D 0.0328 (14) 0.0374 (14) 0.0209 (14) −0.0032 (10) 0.0030 (11) −0.0035 (11)
Cl5D 0.0212 (13) 0.0306 (13) 0.0284 (16) 0.0038 (10) 0.0053 (12) −0.0064 (11)
C1D 0.015 (4) 0.025 (4) 0.013 (5) −0.001 (3) −0.003 (3) −0.002 (3)
C2D 0.013 (4) 0.029 (4) 0.012 (4) −0.007 (3) −0.001 (3) 0.000 (3)
C3D 0.037 (5) 0.014 (4) 0.024 (5) −0.003 (3) 0.007 (4) −0.003 (4)
C4D 0.019 (5) 0.027 (4) 0.011 (5) 0.001 (3) 0.002 (4) 0.000 (4)
C5D 0.016 (4) 0.023 (4) 0.024 (5) 0.008 (3) 0.003 (3) 0.005 (3)
C6D 0.029 (5) 0.017 (4) 0.028 (5) −0.002 (3) 0.010 (4) 0.001 (4)
C7D 0.023 (3) 0.023 (2) 0.018 (2) −0.0027 (19) 0.0032 (19) 0.0011 (19)
C8D 0.020 (3) 0.023 (2) 0.020 (2) 0.0023 (18) 0.004 (2) −0.0017 (19)
C1'D 0.015 (2) 0.017 (2) 0.021 (3) 0.0037 (18) 0.0005 (18) 0.0009 (18)
C2'D 0.023 (2) 0.015 (2) 0.024 (3) −0.0031 (18) 0.005 (2) 0.0013 (18)
C3'D 0.028 (3) 0.015 (2) 0.020 (3) 0.0018 (19) 0.005 (2) 0.0003 (19)
C4'D 0.026 (3) 0.025 (3) 0.018 (3) 0.009 (2) 0.006 (2) 0.005 (2)
C5'D 0.023 (3) 0.029 (3) 0.027 (3) 0.001 (2) 0.007 (2) 0.009 (2)
C6'D 0.021 (2) 0.021 (3) 0.022 (3) −0.004 (2) 0.002 (2) 0.000 (2)
Open in a new tab

Geometric parameters (Å, °)

S1A—O4A 1.425 (6) S1C—O3C 1.399 (8)
S1A—O3A 1.428 (7) S1C—O4C 1.410 (6)
S1A—O2A 1.564 (6) S1C—O2C 1.581 (7)
S1A—O1A 1.571 (6) S1C—O1C 1.586 (6)
O1A—C4A 1.431 (10) O1C—C4C 1.427 (10)
O2A—C7A 1.459 (11) O2C—C7C 1.447 (11)
Cl1A—C3'A 1.736 (7) Cl1C—C3'C 1.716 (7)
Cl2A—C4'A 1.729 (8) Cl2C—C4'C 1.730 (8)
Cl3A—C8A 1.767 (8) Cl3C—C8C 1.756 (8)
Cl4A—C8A 1.765 (10) Cl4C—C8C 1.792 (9)
Cl5A—C8A 1.780 (8) Cl5C—C8C 1.759 (8)
C1A—C2A 1.401 (12) C1C—C6C 1.385 (11)
C1A—C6A 1.406 (11) C1C—C2C 1.391 (12)
C1A—C1'A 1.490 (11) C1C—C1'C 1.490 (12)
C2A—C3A 1.385 (11) C2C—C3C 1.385 (11)
C2A—H2A 0.9500 C2C—H2C 0.9500
C3A—C4A 1.360 (11) C3C—C4C 1.378 (11)
C3A—H3A 0.9500 C3C—H3C 0.9500
C4A—C5A 1.389 (12) C4C—C5C 1.375 (12)
C5A—C6A 1.358 (10) C5C—C6C 1.394 (10)
C5A—H5A 0.9500 C5C—H5C 0.9500
C6A—H6A 0.9500 C6C—H6C 0.9500
C7A—C8A 1.527 (11) C7C—C8C 1.528 (11)
C7A—H7A1 0.9900 C7C—H7C1 0.9900
C7A—H7A2 0.9900 C7C—H7C2 0.9900
C1'A—C2'A 1.372 (11) C1'C—C6'C 1.388 (10)
C1'A—C6'A 1.400 (10) C1'C—C2'C 1.413 (11)
C2'A—C3'A 1.370 (10) C2'C—C3'C 1.399 (10)
C2'A—H2'A 0.9500 C2'C—H2'C 0.9500
C3'A—C4'A 1.407 (10) C3'C—C4'C 1.385 (10)
C4'A—C5'A 1.368 (10) C4'C—C5'C 1.378 (10)
C5'A—C6'A 1.387 (10) C5'C—C6'C 1.399 (10)
C5'A—H5'A 0.9500 C5'C—H5'C 0.9500
C6'A—H6'A 0.9500 C6'C—H6'C 0.9500
S1B—O4B 1.403 (6) S1D—O3D 1.417 (7)
S1B—O3B 1.411 (8) S1D—O4D 1.423 (6)
S1B—O1B 1.584 (6) S1D—O1D 1.563 (6)
S1B—O2B 1.589 (6) S1D—O2D 1.567 (7)
O1B—C4B 1.426 (10) O1D—C4D 1.449 (9)
O2B—C7B 1.449 (11) O2D—C7D 1.469 (11)
Cl1B—C3'B 1.733 (8) Cl1D—C3'D 1.727 (8)
Cl2B—C4'B 1.731 (8) Cl2D—C4'D 1.741 (8)
Cl3B—C8B 1.750 (9) Cl3D—C8D 1.774 (8)
Cl4B—C8B 1.782 (10) Cl4D—C8D 1.788 (10)
Cl5B—C8B 1.756 (9) Cl5D—C8D 1.761 (9)
C1B—C2B 1.392 (12) C1D—C2D 1.407 (11)
C1B—C6B 1.393 (11) C1D—C6D 1.411 (11)
C1B—C1'B 1.520 (12) C1D—C1'D 1.471 (11)
C2B—C3B 1.354 (10) C2D—C3D 1.368 (11)
C2B—H2B 0.9500 C2D—H2D 0.9500
C3B—C4B 1.416 (11) C3D—C4D 1.360 (11)
C3B—H3B 0.9500 C3D—H3D 0.9500
C4B—C5B 1.372 (11) C4D—C5D 1.363 (11)
C5B—C6B 1.365 (10) C5D—C6D 1.380 (10)
C5B—H5B 0.9500 C5D—H5D 0.9500
C6B—H6B 0.9500 C6D—H6D 0.9500
C7B—C8B 1.543 (12) C7D—C8D 1.518 (12)
C7B—H7B1 0.9900 C7D—H7D1 0.9900
C7B—H7B2 0.9900 C7D—H7D2 0.9900
C1'B—C6'B 1.381 (10) C1'D—C2'D 1.376 (11)
C1'B—C2'B 1.413 (11) C1'D—C6'D 1.401 (10)
C2'B—C3'B 1.382 (10) C2'D—C3'D 1.388 (10)
C2'B—H2'B 0.9500 C2'D—H2'D 0.9500
C3'B—C4'B 1.387 (10) C3'D—C4'D 1.387 (10)
C4'B—C5'B 1.393 (10) C4'D—C5'D 1.379 (11)
C5'B—C6'B 1.373 (10) C5'D—C6'D 1.383 (10)
C5'B—H5'B 0.9500 C5'D—H5'D 0.9500
C6'B—H6'B 0.9500 C6'D—H6'D 0.9500
O4A—S1A—O3A 122.5 (4) O3C—S1C—O4C 122.9 (4)
O4A—S1A—O2A 109.4 (4) O3C—S1C—O2C 105.2 (4)
O3A—S1A—O2A 105.1 (4) O4C—S1C—O2C 109.0 (4)
O4A—S1A—O1A 104.9 (4) O3C—S1C—O1C 110.6 (4)
O3A—S1A—O1A 109.7 (4) O4C—S1C—O1C 104.7 (4)
O2A—S1A—O1A 103.9 (3) O2C—S1C—O1C 102.7 (3)
C4A—O1A—S1A 118.0 (6) C4C—O1C—S1C 117.9 (6)
C7A—O2A—S1A 116.1 (5) C7C—O2C—S1C 116.2 (5)
C2A—C1A—C6A 116.9 (8) C6C—C1C—C2C 119.2 (8)
C2A—C1A—C1'A 121.8 (7) C6C—C1C—C1'C 119.5 (8)
C6A—C1A—C1'A 121.3 (8) C2C—C1C—C1'C 121.2 (7)
C3A—C2A—C1A 121.3 (8) C3C—C2C—C1C 120.3 (8)
C3A—C2A—H2A 119.3 C3C—C2C—H2C 119.8
C1A—C2A—H2A 119.3 C1C—C2C—H2C 119.8
C4A—C3A—C2A 118.8 (8) C4C—C3C—C2C 119.3 (8)
C4A—C3A—H3A 120.6 C4C—C3C—H3C 120.3
C2A—C3A—H3A 120.6 C2C—C3C—H3C 120.3
C3A—C4A—C5A 122.4 (8) C5C—C4C—C3C 121.6 (8)
C3A—C4A—O1A 120.2 (8) C5C—C4C—O1C 118.3 (7)
C5A—C4A—O1A 117.3 (8) C3C—C4C—O1C 120.0 (8)
C6A—C5A—C4A 118.1 (8) C4C—C5C—C6C 118.7 (7)
C6A—C5A—H5A 121.0 C4C—C5C—H5C 120.6
C4A—C5A—H5A 121.0 C6C—C5C—H5C 120.6
C5A—C6A—C1A 122.5 (8) C1C—C6C—C5C 120.7 (8)
C5A—C6A—H6A 118.7 C1C—C6C—H6C 119.7
C1A—C6A—H6A 118.7 C5C—C6C—H6C 119.7
O2A—C7A—C8A 107.0 (7) O2C—C7C—C8C 106.0 (7)
O2A—C7A—H7A1 110.3 O2C—C7C—H7C1 110.5
C8A—C7A—H7A1 110.3 C8C—C7C—H7C1 110.5
O2A—C7A—H7A2 110.3 O2C—C7C—H7C2 110.5
C8A—C7A—H7A2 110.3 C8C—C7C—H7C2 110.5
H7A1—C7A—H7A2 108.6 H7C1—C7C—H7C2 108.7
C7A—C8A—Cl4A 106.6 (6) C7C—C8C—Cl3C 110.8 (6)
C7A—C8A—Cl3A 111.0 (6) C7C—C8C—Cl5C 111.4 (6)
Cl4A—C8A—Cl3A 109.9 (4) Cl3C—C8C—Cl5C 110.4 (5)
C7A—C8A—Cl5A 110.7 (5) C7C—C8C—Cl4C 105.7 (6)
Cl4A—C8A—Cl5A 109.7 (5) Cl3C—C8C—Cl4C 109.1 (4)
Cl3A—C8A—Cl5A 108.9 (5) Cl5C—C8C—Cl4C 109.3 (5)
C2'A—C1'A—C6'A 119.2 (7) C6'C—C1'C—C2'C 117.7 (7)
C2'A—C1'A—C1A 122.5 (7) C6'C—C1'C—C1C 122.4 (7)
C6'A—C1'A—C1A 118.3 (7) C2'C—C1'C—C1C 119.9 (7)
C3'A—C2'A—C1'A 121.4 (7) C3'C—C2'C—C1'C 120.2 (7)
C3'A—C2'A—H2'A 119.3 C3'C—C2'C—H2'C 119.9
C1'A—C2'A—H2'A 119.3 C1'C—C2'C—H2'C 119.9
C2'A—C3'A—C4'A 120.0 (7) C4'C—C3'C—C2'C 120.5 (7)
C2'A—C3'A—Cl1A 120.2 (6) C4'C—C3'C—Cl1C 120.9 (6)
C4'A—C3'A—Cl1A 119.8 (6) C2'C—C3'C—Cl1C 118.5 (6)
C5'A—C4'A—C3'A 118.7 (7) C5'C—C4'C—C3'C 119.8 (7)
C5'A—C4'A—Cl2A 120.5 (6) C5'C—C4'C—Cl2C 119.6 (6)
C3'A—C4'A—Cl2A 120.8 (6) C3'C—C4'C—Cl2C 120.6 (6)
C4'A—C5'A—C6'A 121.4 (7) C4'C—C5'C—C6'C 119.9 (7)
C4'A—C5'A—H5'A 119.3 C4'C—C5'C—H5'C 120.0
C6'A—C5'A—H5'A 119.3 C6'C—C5'C—H5'C 120.0
C5'A—C6'A—C1'A 119.3 (7) C1'C—C6'C—C5'C 121.7 (7)
C5'A—C6'A—H6'A 120.4 C1'C—C6'C—H6'C 119.2
C1'A—C6'A—H6'A 120.4 C5'C—C6'C—H6'C 119.2
O4B—S1B—O3B 122.1 (4) O3D—S1D—O4D 122.9 (4)
O4B—S1B—O1B 104.6 (4) O3D—S1D—O1D 109.8 (4)
O3B—S1B—O1B 110.8 (4) O4D—S1D—O1D 105.1 (4)
O4B—S1B—O2B 109.8 (4) O3D—S1D—O2D 105.3 (4)
O3B—S1B—O2B 105.1 (4) O4D—S1D—O2D 109.3 (4)
O1B—S1B—O2B 103.1 (3) O1D—S1D—O2D 102.7 (4)
C4B—O1B—S1B 119.8 (6) C4D—O1D—S1D 120.7 (6)
C7B—O2B—S1B 115.8 (5) C7D—O2D—S1D 116.0 (5)
C2B—C1B—C6B 117.8 (8) C2D—C1D—C6D 115.7 (7)
C2B—C1B—C1'B 120.5 (7) C2D—C1D—C1'D 123.1 (7)
C6B—C1B—C1'B 121.7 (8) C6D—C1D—C1'D 121.1 (7)
C3B—C2B—C1B 122.5 (8) C3D—C2D—C1D 122.0 (8)
C3B—C2B—H2B 118.8 C3D—C2D—H2D 119.0
C1B—C2B—H2B 118.8 C1D—C2D—H2D 119.0
C2B—C3B—C4B 117.7 (8) C4D—C3D—C2D 119.1 (8)
C2B—C3B—H3B 121.2 C4D—C3D—H3D 120.5
C4B—C3B—H3B 121.2 C2D—C3D—H3D 120.5
C5B—C4B—C3B 121.2 (8) C3D—C4D—C5D 122.7 (8)
C5B—C4B—O1B 117.5 (8) C3D—C4D—O1D 121.1 (8)
C3B—C4B—O1B 121.2 (8) C5D—C4D—O1D 116.1 (7)
C6B—C5B—C4B 119.1 (8) C4D—C5D—C6D 118.0 (8)
C6B—C5B—H5B 120.4 C4D—C5D—H5D 121.0
C4B—C5B—H5B 120.4 C6D—C5D—H5D 121.0
C5B—C6B—C1B 121.5 (8) C5D—C6D—C1D 122.4 (7)
C5B—C6B—H6B 119.2 C5D—C6D—H6D 118.8
C1B—C6B—H6B 119.2 C1D—C6D—H6D 118.8
O2B—C7B—C8B 105.3 (7) O2D—C7D—C8D 105.4 (7)
O2B—C7B—H7B1 110.7 O2D—C7D—H7D1 110.7
C8B—C7B—H7B1 110.7 C8D—C7D—H7D1 110.7
O2B—C7B—H7B2 110.7 O2D—C7D—H7D2 110.7
C8B—C7B—H7B2 110.7 C8D—C7D—H7D2 110.7
H7B1—C7B—H7B2 108.8 H7D1—C7D—H7D2 108.8
C7B—C8B—Cl3B 111.1 (6) C7D—C8D—Cl5D 111.2 (6)
C7B—C8B—Cl5B 109.9 (6) C7D—C8D—Cl3D 111.4 (6)
Cl3B—C8B—Cl5B 110.6 (5) Cl5D—C8D—Cl3D 109.6 (5)
C7B—C8B—Cl4B 105.2 (6) C7D—C8D—Cl4D 105.4 (6)
Cl3B—C8B—Cl4B 110.1 (5) Cl5D—C8D—Cl4D 110.0 (5)
Cl5B—C8B—Cl4B 109.8 (5) Cl3D—C8D—Cl4D 109.1 (5)
C6'B—C1'B—C2'B 119.1 (7) C2'D—C1'D—C6'D 117.1 (7)
C6'B—C1'B—C1B 121.1 (7) C2'D—C1'D—C1D 120.7 (7)
C2'B—C1'B—C1B 119.7 (7) C6'D—C1'D—C1D 122.2 (7)
C3'B—C2'B—C1'B 119.6 (7) C1'D—C2'D—C3'D 122.3 (7)
C3'B—C2'B—H2'B 120.2 C1'D—C2'D—H2'D 118.9
C1'B—C2'B—H2'B 120.2 C3'D—C2'D—H2'D 118.9
C2'B—C3'B—C4'B 120.3 (7) C4'D—C3'D—C2'D 119.4 (7)
C2'B—C3'B—Cl1B 118.5 (6) C4'D—C3'D—Cl1D 121.1 (6)
C4'B—C3'B—Cl1B 121.1 (6) C2'D—C3'D—Cl1D 119.5 (6)
C3'B—C4'B—C5'B 119.9 (7) C5'D—C4'D—C3'D 119.8 (7)
C3'B—C4'B—Cl2B 120.3 (6) C5'D—C4'D—Cl2D 120.0 (6)
C5'B—C4'B—Cl2B 119.7 (6) C3'D—C4'D—Cl2D 120.2 (6)
C6'B—C5'B—C4'B 119.8 (7) C4'D—C5'D—C6'D 119.9 (7)
C6'B—C5'B—H5'B 120.1 C4'D—C5'D—H5'D 120.1
C4'B—C5'B—H5'B 120.1 C6'D—C5'D—H5'D 120.1
C5'B—C6'B—C1'B 121.2 (7) C5'D—C6'D—C1'D 121.6 (7)
C5'B—C6'B—H6'B 119.4 C5'D—C6'D—H6'D 119.2
C1'B—C6'B—H6'B 119.4 C1'D—C6'D—H6'D 119.2
O4A—S1A—O1A—C4A 158.0 (6) O3C—S1C—O1C—C4C −20.6 (7)
O3A—S1A—O1A—C4A 24.7 (7) O4C—S1C—O1C—C4C −154.9 (6)
O2A—S1A—O1A—C4A −87.2 (7) O2C—S1C—O1C—C4C 91.3 (7)
O4A—S1A—O2A—C7A 36.5 (7) O3C—S1C—O2C—C7C −169.1 (6)
O3A—S1A—O2A—C7A 169.7 (6) O4C—S1C—O2C—C7C −35.6 (7)
O1A—S1A—O2A—C7A −75.1 (6) O1C—S1C—O2C—C7C 75.1 (6)
C6A—C1A—C2A—C3A −1.5 (12) C6C—C1C—C2C—C3C −1.3 (13)
C1'A—C1A—C2A—C3A −179.5 (8) C1'C—C1C—C2C—C3C −179.9 (8)
C1A—C2A—C3A—C4A −0.2 (12) C1C—C2C—C3C—C4C −1.1 (13)
C2A—C3A—C4A—C5A 1.2 (13) C2C—C3C—C4C—C5C 1.4 (14)
C2A—C3A—C4A—O1A 177.4 (7) C2C—C3C—C4C—O1C −175.2 (8)
S1A—O1A—C4A—C3A 91.2 (9) S1C—O1C—C4C—C5C 89.0 (9)
S1A—O1A—C4A—C5A −92.4 (8) S1C—O1C—C4C—C3C −94.3 (9)
C3A—C4A—C5A—C6A −0.5 (13) C3C—C4C—C5C—C6C 0.7 (14)
O1A—C4A—C5A—C6A −176.8 (7) O1C—C4C—C5C—C6C 177.4 (7)
C4A—C5A—C6A—C1A −1.3 (13) C2C—C1C—C6C—C5C 3.4 (13)
C2A—C1A—C6A—C5A 2.2 (13) C1'C—C1C—C6C—C5C −177.9 (8)
C1'A—C1A—C6A—C5A −179.7 (8) C4C—C5C—C6C—C1C −3.1 (13)
S1A—O2A—C7A—C8A 167.0 (5) S1C—O2C—C7C—C8C −164.1 (5)
O2A—C7A—C8A—Cl4A 177.8 (5) O2C—C7C—C8C—Cl3C −60.2 (7)
O2A—C7A—C8A—Cl3A 58.1 (7) O2C—C7C—C8C—Cl5C 63.1 (8)
O2A—C7A—C8A—Cl5A −62.9 (7) O2C—C7C—C8C—Cl4C −178.3 (5)
C2A—C1A—C1'A—C2'A 152.5 (8) C6C—C1C—C1'C—C6'C −148.8 (8)
C6A—C1A—C1'A—C2'A −25.4 (13) C2C—C1C—C1'C—C6'C 29.8 (13)
C2A—C1A—C1'A—C6'A −29.5 (12) C6C—C1C—C1'C—C2'C 30.5 (12)
C6A—C1A—C1'A—C6'A 152.5 (8) C2C—C1C—C1'C—C2'C −150.9 (8)
C6'A—C1'A—C2'A—C3'A 0.2 (12) C6'C—C1'C—C2'C—C3'C 0.8 (12)
C1A—C1'A—C2'A—C3'A 178.2 (8) C1C—C1'C—C2'C—C3'C −178.6 (8)
C1'A—C2'A—C3'A—C4'A 1.1 (12) C1'C—C2'C—C3'C—C4'C −2.6 (12)
C1'A—C2'A—C3'A—Cl1A −175.7 (7) C1'C—C2'C—C3'C—Cl1C 176.0 (6)
C2'A—C3'A—C4'A—C5'A −0.5 (12) C2'C—C3'C—C4'C—C5'C 2.4 (12)
Cl1A—C3'A—C4'A—C5'A 176.3 (6) Cl1C—C3'C—C4'C—C5'C −176.2 (6)
C2'A—C3'A—C4'A—Cl2A 177.9 (6) C2'C—C3'C—C4'C—Cl2C −178.3 (6)
Cl1A—C3'A—C4'A—Cl2A −5.3 (10) Cl1C—C3'C—C4'C—Cl2C 3.0 (10)
C3'A—C4'A—C5'A—C6'A −1.5 (12) C3'C—C4'C—C5'C—C6'C −0.4 (12)
Cl2A—C4'A—C5'A—C6'A −179.9 (6) Cl2C—C4'C—C5'C—C6'C −179.7 (6)
C4'A—C5'A—C6'A—C1'A 2.9 (12) C2'C—C1'C—C6'C—C5'C 1.2 (12)
C2'A—C1'A—C6'A—C5'A −2.2 (12) C1C—C1'C—C6'C—C5'C −179.4 (8)
C1A—C1'A—C6'A—C5'A 179.8 (8) C4'C—C5'C—C6'C—C1'C −1.4 (12)
O4B—S1B—O1B—C4B −159.3 (7) O3D—S1D—O1D—C4D 21.9 (8)
O3B—S1B—O1B—C4B −26.0 (8) O4D—S1D—O1D—C4D 155.9 (7)
O2B—S1B—O1B—C4B 85.9 (7) O2D—S1D—O1D—C4D −89.7 (7)
O4B—S1B—O2B—C7B −37.4 (7) O3D—S1D—O2D—C7D 171.3 (6)
O3B—S1B—O2B—C7B −170.4 (6) O4D—S1D—O2D—C7D 37.4 (7)
O1B—S1B—O2B—C7B 73.5 (6) O1D—S1D—O2D—C7D −73.8 (6)
C6B—C1B—C2B—C3B −2.6 (13) C6D—C1D—C2D—C3D −1.8 (12)
C1'B—C1B—C2B—C3B 179.6 (8) C1'D—C1D—C2D—C3D 179.8 (8)
C1B—C2B—C3B—C4B 4.0 (13) C1D—C2D—C3D—C4D −0.6 (13)
C2B—C3B—C4B—C5B −1.8 (13) C2D—C3D—C4D—C5D 2.8 (14)
C2B—C3B—C4B—O1B 179.5 (7) C2D—C3D—C4D—O1D 179.2 (7)
S1B—O1B—C4B—C5B 123.2 (8) S1D—O1D—C4D—C3D 62.7 (11)
S1B—O1B—C4B—C3B −58.1 (11) S1D—O1D—C4D—C5D −120.7 (8)
C3B—C4B—C5B—C6B −1.6 (13) C3D—C4D—C5D—C6D −2.3 (14)
O1B—C4B—C5B—C6B 177.1 (8) O1D—C4D—C5D—C6D −178.8 (7)
C4B—C5B—C6B—C1B 3.0 (13) C4D—C5D—C6D—C1D −0.4 (12)
C2B—C1B—C6B—C5B −1.0 (13) C2D—C1D—C6D—C5D 2.4 (12)
C1'B—C1B—C6B—C5B 176.8 (8) C1'D—C1D—C6D—C5D −179.2 (8)
S1B—O2B—C7B—C8B −167.3 (5) S1D—O2D—C7D—C8D 166.1 (5)
O2B—C7B—C8B—Cl3B −59.0 (7) O2D—C7D—C8D—Cl5D −62.1 (7)
O2B—C7B—C8B—Cl5B 63.8 (7) O2D—C7D—C8D—Cl3D 60.5 (7)
O2B—C7B—C8B—Cl4B −178.1 (5) O2D—C7D—C8D—Cl4D 178.7 (5)
C2B—C1B—C1'B—C6'B −27.4 (13) C2D—C1D—C1'D—C2'D −159.1 (8)
C6B—C1B—C1'B—C6'B 154.9 (8) C6D—C1D—C1'D—C2'D 22.6 (13)
C2B—C1B—C1'B—C2'B 156.4 (8) C2D—C1D—C1'D—C6'D 22.8 (13)
C6B—C1B—C1'B—C2'B −21.3 (13) C6D—C1D—C1'D—C6'D −155.4 (8)
C6'B—C1'B—C2'B—C3'B 0.8 (12) C6'D—C1'D—C2'D—C3'D 0.9 (12)
C1B—C1'B—C2'B—C3'B 177.1 (7) C1D—C1'D—C2'D—C3'D −177.2 (8)
C1'B—C2'B—C3'B—C4'B −2.0 (12) C1'D—C2'D—C3'D—C4'D −0.7 (12)
C1'B—C2'B—C3'B—Cl1B 180.0 (6) C1'D—C2'D—C3'D—Cl1D 179.3 (6)
C2'B—C3'B—C4'B—C5'B 2.9 (12) C2'D—C3'D—C4'D—C5'D −0.1 (12)
Cl1B—C3'B—C4'B—C5'B −179.1 (6) Cl1D—C3'D—C4'D—C5'D 179.9 (6)
C2'B—C3'B—C4'B—Cl2B 179.1 (6) C2'D—C3'D—C4'D—Cl2D 178.2 (6)
Cl1B—C3'B—C4'B—Cl2B −2.9 (10) Cl1D—C3'D—C4'D—Cl2D −1.8 (10)
C3'B—C4'B—C5'B—C6'B −2.7 (12) C3'D—C4'D—C5'D—C6'D 0.7 (12)
Cl2B—C4'B—C5'B—C6'B −178.9 (6) Cl2D—C4'D—C5'D—C6'D −177.7 (6)
C4'B—C5'B—C6'B—C1'B 1.5 (12) C4'D—C5'D—C6'D—C1'D −0.4 (12)
C2'B—C1'B—C6'B—C5'B −0.6 (12) C2'D—C1'D—C6'D—C5'D −0.3 (12)
C1B—C1'B—C6'B—C5'B −176.8 (8) C1D—C1'D—C6'D—C5'D 177.7 (8)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5052).

References

  1. Brandao, T. A. S., Priebe, J. P., Damasceno, A. S., Bortoluzzia, A. J., Kirby, A. J. & Nome, F. (2005). J. Mol. Struct.734, 205–209.
  2. Carpenter, J. E., Baker, J., Hehre, W. J. & Khan, S. D. (1980). SPARTAN Wavefunction Inc., Irvine, CA, USA.
  3. Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  4. Lehmler, H.-J., Parkin, S. & Robertson, L. W. (2002). Chemosphere, 46, 485–488. [DOI] [PubMed]
  5. Letcher, R. J., Klasson-Wehler, E. & Bergman, A. (2000). The handbook of environmental chemistry, Vol. 3, Part K: New types of persistent halogenated compounds, edited by J. Paasivirta, pp. 315–359. Berlin, Heidelberg: Springer Verlag.
  6. Li, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010a). Acta Cryst. E66, o1073. [DOI] [PMC free article] [PubMed]
  7. Li, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010b). Environ. Int., doi:10.1016/j.envint.2009.1002.1005. [DOI] [PMC free article] [PubMed]
  8. Li, X., Parkin, S., Robertson, L. W. & Lehmler, H.-J. (2008). Acta Cryst. E64, o2464. [DOI] [PMC free article] [PubMed]
  9. Liu, Y., Apak, T. I., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2006). Chem. Res. Toxicol.19, 1420–1425. [DOI] [PubMed]
  10. Liu, Y., Lien, I. F. F., Ruttgaizer, S., Dove, P. & Taylor, S. D. (2004a). Org. Lett.6, 209–212. [DOI] [PubMed]
  11. Liu, Y., Lien, I. F. F., Ruttgaizer, S., Dove, P. & Taylor, S. D. (2004b). Org. Lett.6, 209–212. [DOI] [PubMed]
  12. Liu, Y., Smart, J. T., Song, Y., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2009). Drug Metab. Dispos.37, 1065–1072. [DOI] [PMC free article] [PubMed]
  13. Nonius (1998). COLLECT Nonius BV, Delft, The Netherlands.
  14. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  15. Robertson, L. W. & Hansen, L. G. (2001). Recent advances in the environmental toxicology and health effects of PCBs. Lexington: University Press of Kentucky.
  16. Sacco, J. C. & James, M. O. (2005). Drug Metab. Dispos.33, 1341–1348. [DOI] [PubMed]
  17. Shaikh, N. S., Parkin, S., Luthe, G. & Lehmler, H. J. (2008). Chemosphere, 70, 1694–1698. [DOI] [PMC free article] [PubMed]
  18. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  19. Tampal, N., Lehmler, H.-J., Espandiari, P., Malmberg, T. & Robertson, L. W. (2002). Chem. Res. Toxicol.15, 1259–1266. [DOI] [PubMed]
  20. Vyas, S. M., Parkin, S. & Lehmler, H.-J. (2006). Acta Cryst. E62, o2905–o2906.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020362/lh5052sup1.cif

e-66-o1615-sup1.cif (42.9KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020362/lh5052Isup2.hkl

e-66-o1615-Isup2.hkl (716.1KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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