organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4′-Chloro­bi­phenyl-4-yl 2,2,2-tri­chloro­ethyl sulfate

aThe University of Iowa, Department of Occupational and Environmental Health, 100 Oakdale Campus, 124 IREH, Iowa City, IA 52242-5000, USA, and bUniversity of Kentucky, Department of Chemistry, Lexington, KY 40506-0055, USA
*Correspondence e-mail: hans-joachim-lehmler@uiowa.edu

(Received 5 November 2008; accepted 19 November 2008; online 29 November 2008)

The title compound, C14H10Cl4O4S, is an inter­mediate in the synthesis of the PCB sulfate monoester of 4′-chloro-biphenyl-4-ol. Both the sulfate monoester and 4′-chloro-biphenyl-4-ol are metabolites of PCB 3 (4-chloro­biphen­yl). There are two mol­ecules with different conformations in the asymmetric unit. The solid state dihedral angles between the benzene rings are 18.52 (10) and 41.84 (16)° in the two mol­ecules, whereas the dihedral angles between the least-squares plane of the sulfated benzene ring and O—S (Ar—C—O—S) are 66.2 (3) and 89.3 (3)°. The crystal was an inversion twin with a refined component fraction of 0.44 (7).

Related literature

For similar structures of hydroxy­lated chloro­biphenyls and their derivatives, see: Rissanen et al. (1988a[Rissanen, K., Valkonen, J. & Mannila, B. (1988a). Acta Cryst. C44, 682-684.],b[Rissanen, K., Valkonen, J. & Mannila, B. (1988b). Acta Cryst. C44, 684-686.]); Lehmler et al. (2001[Lehmler, H.-J., Robertson, L. W. & Parkin, S. (2001). Acta Cryst. E57, o590-o591.], 2002[Lehmler, H.-J., Robertson, L. W., Parkin, S. & Brock, C. P. (2002). Acta Cryst. B58, 140-147.]); Desiraju et al. (1979[Desiraju, G. R., Paul, I. C. & Curtin, D. Y. (1979). Mol. Cryst. Liq. Cryst. 52, 259-266.]); Vyas et al. (2006[Vyas, S. M., Parkin, S. & Lehmler, H.-J. (2006). Acta Cryst. E62, o2905-o2906.]). For a review of structures of sulfuric acid aryl mono esters, see: Brandao et al. (2005[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.]). For additional background, see: Letcher et al. (2000[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.]); Liu et al. (2004[Liu, Y., Lien, I. F. F., Ruttgaizer, S., Dove, P. & Taylor, S. D. (2004). Org. Lett. 6, 209-212.], 2006[Liu, Y., Apak, T. I., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2006). Chem. Res. Toxicol. 19, 1420-1425.]); Sacco & James (2005[Sacco, J. C. & James, M. O. (2005). Drug Metab. Dispos. 33, 1341-1348.]); Shaikh et al. (2008[Shaikh, N. S., Parkin, S., Luthe, G. & Lehmler, H. J. (2008). Chemosphere, 70, 1694-1698.]); Tampal et al. (2002[Tampal, N., Lehmler, H.-J., Espandiari, P., Malmberg, T. & Robertson, L. W. (2002). Chem. Res. Toxicol. 15, 1259-1266.]); Hansen (1999[Hansen, L. G. (1999). The Ortho Side of PCBs. Boston: Kluwer Academic Publishers.]); Robertson & Hansen (2001[Robertson, L. W. & Hansen, L. G. (2001). Recent Advances in the Environmental Toxicology and Health Effects of PCBs. Lexington, USA: University Press of Kentucky.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10Cl4O4S

  • Mr = 416.08

  • Orthorhombic, P c a 21

  • a = 9.6305 (19) Å

  • b = 30.273 (6) Å

  • c = 11.330 (2) Å

  • V = 3303.3 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.86 mm−1

  • T = 90.0 (2) K

  • 0.40 × 0.34 × 0.18 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[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.]) Tmin = 0.679, Tmax = 0.861

  • 25566 measured reflections

  • 6476 independent reflections

  • 4862 reflections with I > 2σ(I)

  • Rint = 0.063

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.109

  • S = 1.05

  • 6476 reflections

  • 415 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.56 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2481 Friedel Pairs

  • Flack parameter: 0.44 (7)

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: DENZO-SMN (Otwinowski & Minor, 1997[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.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and local procedures.

Supporting information


Comment top

Polychlorinated biphenyls (PCBs) are a major class of man-made, persistent organic pollutants and represent an environmental and health concern due to their toxicity and resistance to biodegradation (Robertson & Hansen, 2001; Hansen, 1999). PCB congeners with a lower degree of chlorination are especially prone to undergo oxidative metabolism to hydroxylated (OH)-PCBs (Letcher et al., 2000). OH-PCBs can be further transformed to glucuronides (Tampal et al., 2002) or sulfates (Liu et al., 2006, Sacco & James, 2005). These PCB metabolites are more hydrophilic than PCBs and OH-PCBs and are expected to be more easily excreted. Despite the potential importance of sulfated PCB metabolites, PCB sulfate monoesters and analogous compounds have not been synthesized experimentally and their detailed molecular structure is unknown. Similarly, only few structures of hydroxylated chlorobiphenyl derivatives (Rissanen et al. 1988a, 1988b; Lehmler et al., 2001, 2002; Desiraju et al., 1979; Vyas et al., 2006) and sulfuric acid aryl mono esters (Brandao et al., 2005) have been reported.

Herein we report the crystal structure of the title compound, a trichloro-ethyl PCB sulfate diester intermediate of a putative sulfate metabolite of PCB3 (4-chlorobiphenyl). The asymmetric unit of the crystal structure contains two molecules with different conformations (Fig. 1), an observation that highlights the flexibility of PCB derivatives that lack multiple ortho chlorine substituents. The dihedral angles between the two benzene rings in the biphenyl moiety are 18.52 (10)° and 41.84 (16)° for molecules A and B, respectively. Similar to molecule B, other PCB derivatives with no ortho chlorine substituent adopt dihedral angles of 39.42° (4,4'-dichhlorobiphenyl), 41.31 (07)° (3,3',5'-trichloro-4-methoxy-biphenyl) and 43.94 (06)° (3,3',4,4'-tetrachlorobiphenyl) in the solid state (Shaikh et al., 2008). The calculated dihedral angle of the title compound is 41.2° (Shaikh et al., 2008), which is comparable to that of molecule B, but significantly larger than that of molecule A. The dihedral angle formed by the least-squares plane of the sulfated benzene ring and O1—S1 (Ar—C4—O1—S1) was 66.2 (3)° and 89.3 (3)° for molecules A and B, respectively. These dihedral angles are larger than the calculated Ar—C4—O1—S1 dihedral angle of approximately 54° (calculated with AM1 as implemented by ArgusLab, Version 4.0.1). Overall, these deviations from the energetically most favorable conformation of the title compound are due to crystal packing effects, which allow the molecule to adopt an energetically unfavorable conformation to maximize intermolecular interactions, and thus the lattice energy in the crystal.

Related literature top

For similar structures of hydroxylated chlorobiphenyls and their derivatives, see: Rissanen et al. (1988a,b); Lehmler et al. (2001, 2002); Desiraju et al. (1979); Vyas et al. (2006). For a review of structures of sulfuric acid aryl mono esters, see: Brandao et al. (2005). For additional background, see: Letcher et al. (2000); Liu et al. (2004, 2006); Sacco & James (2005); Shaikh et al. (2008); Tampal et al. (2002); Hansen (1999); Robertson & Hansen (2001).

Experimental top

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

Refinement top

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 C atom.

The crystal was an inversion twin with a refined component fraction of 0.44 (7), i.e. essentially equal amounts of each component.

Computing details top

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: SHELX97 (Sheldrick, 2008) and local procedures.

Figures top
[Figure 1] Fig. 1. View of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
4'-Chlorobiphenyl-4-yl 2,2,2-trichloroethyl sulfate top
Crystal data top
C14H10Cl4O4SF(000) = 1680
Mr = 416.08Dx = 1.673 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 4257 reflections
a = 9.6305 (19) Åθ = 1.0–27.5°
b = 30.273 (6) ŵ = 0.86 mm1
c = 11.330 (2) ÅT = 90 K
V = 3303.3 (11) Å3Block, colourless
Z = 80.40 × 0.34 × 0.18 mm
Data collection top
Nonius KappaCCD
diffractometer
6476 independent reflections
Radiation source: fine-focus sealed tube4862 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.2°
ω scans at fixed χ = 55°h = 1212
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 3938
Tmin = 0.679, Tmax = 0.861l = 1114
25566 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0569P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
6476 reflectionsΔρmax = 0.51 e Å3
415 parametersΔρmin = 0.56 e Å3
1 restraintAbsolute structure: Flack (1983), 2481 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.44 (7)
Crystal data top
C14H10Cl4O4SV = 3303.3 (11) Å3
Mr = 416.08Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 9.6305 (19) ŵ = 0.86 mm1
b = 30.273 (6) ÅT = 90 K
c = 11.330 (2) Å0.40 × 0.34 × 0.18 mm
Data collection top
Nonius KappaCCD
diffractometer
6476 independent reflections
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
4862 reflections with I > 2σ(I)
Tmin = 0.679, Tmax = 0.861Rint = 0.063
25566 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.51 e Å3
S = 1.05Δρmin = 0.56 e Å3
6476 reflectionsAbsolute structure: Flack (1983), 2481 Friedel Pairs
415 parametersAbsolute structure parameter: 0.44 (7)
1 restraint
Special details top

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.37972 (11)0.52517 (4)0.22349 (11)0.0182 (3)
O1A0.4951 (3)0.55663 (9)0.2732 (3)0.0189 (7)
O2A0.3525 (3)0.49236 (9)0.3284 (3)0.0162 (7)
O3A0.2535 (3)0.54799 (8)0.2091 (3)0.0228 (7)
O4A0.4438 (3)0.50234 (10)0.1291 (3)0.0219 (7)
Cl1A0.32327 (13)0.81401 (4)0.83893 (12)0.0332 (3)
Cl2A0.34106 (12)0.39176 (4)0.28495 (11)0.0249 (3)
Cl3A0.55811 (11)0.39177 (4)0.46162 (11)0.0250 (3)
Cl4A0.28608 (11)0.42787 (4)0.51617 (10)0.0251 (3)
C1A0.4100 (4)0.66199 (14)0.5036 (4)0.0185 (10)
C2A0.4593 (5)0.66887 (14)0.3888 (4)0.0253 (10)
H2A0.47770.69810.36270.030*
C3A0.4817 (4)0.63383 (14)0.3129 (4)0.0255 (11)
H3A0.51290.63900.23460.031*
C4A0.4583 (4)0.59162 (14)0.3517 (4)0.0169 (10)
C5A0.4137 (4)0.58287 (15)0.4644 (4)0.0192 (10)
H5A0.40020.55340.49050.023*
C6A0.3889 (4)0.61848 (14)0.5396 (4)0.0203 (11)
H6A0.35670.61290.61740.024*
C7A0.4706 (4)0.46577 (13)0.3666 (4)0.0171 (10)
H7A10.51920.48040.43290.021*
H7A20.53710.46190.30080.021*
C8A0.4136 (4)0.42113 (14)0.4058 (4)0.0174 (10)
C1'A0.3849 (4)0.69949 (14)0.5865 (4)0.0202 (10)
C2'A0.3782 (4)0.69245 (14)0.7090 (4)0.0229 (10)
H2'A0.38820.66340.73930.028*
C3'A0.3573 (5)0.72738 (14)0.7862 (4)0.0278 (11)
H3'A0.35190.72240.86890.033*
C4'A0.3444 (5)0.76930 (14)0.7414 (4)0.0215 (11)
C5'A0.3477 (4)0.77735 (13)0.6205 (4)0.0265 (11)
H5'A0.33510.80640.59050.032*
C6'A0.3696 (5)0.74235 (14)0.5456 (4)0.0259 (11)
H6'A0.37440.74770.46310.031*
S1B0.36151 (11)0.02678 (3)0.20279 (10)0.0170 (2)
O1B0.4725 (3)0.06109 (9)0.1597 (3)0.0197 (7)
O2B0.3431 (3)0.00442 (9)0.0931 (3)0.0180 (7)
O3B0.2310 (3)0.04755 (8)0.2178 (3)0.0214 (7)
O4B0.4277 (3)0.00352 (10)0.2956 (3)0.0210 (7)
Cl1B0.29897 (13)0.31088 (4)0.42521 (12)0.0308 (3)
Cl2B0.30154 (11)0.06864 (4)0.10670 (11)0.0226 (3)
Cl3B0.55924 (11)0.10661 (4)0.02190 (12)0.0258 (3)
Cl4B0.31521 (12)0.10380 (4)0.12863 (11)0.0249 (3)
C1B0.3812 (5)0.16175 (14)0.0805 (4)0.0198 (10)
C2B0.4206 (4)0.12024 (14)0.1204 (4)0.0201 (10)
H2B0.42930.11490.20270.024*
C3B0.4471 (4)0.08652 (15)0.0409 (5)0.0223 (11)
H3B0.47450.05810.06800.027*
C4B0.4335 (4)0.09461 (14)0.0765 (5)0.0183 (10)
C5B0.3896 (4)0.13457 (13)0.1210 (4)0.0225 (10)
H5B0.37880.13900.20350.027*
C6B0.3617 (5)0.16827 (13)0.0406 (4)0.0218 (10)
H6B0.32910.19600.06840.026*
C7B0.4627 (4)0.03186 (14)0.0616 (4)0.0182 (10)
H7B10.52310.03620.13130.022*
H7B20.51770.01730.00110.022*
C8B0.4097 (4)0.07557 (14)0.0186 (4)0.0171 (10)
C1'B0.3608 (4)0.19884 (14)0.1657 (4)0.0189 (10)
C2'B0.2482 (5)0.22865 (12)0.1553 (4)0.0239 (10)
H2'B0.18340.22500.09280.029*
C3'B0.2307 (5)0.26276 (13)0.2336 (4)0.0236 (10)
H3'B0.15530.28270.22450.028*
C4'B0.3228 (5)0.26804 (14)0.3252 (4)0.0226 (11)
C5'B0.4350 (5)0.23942 (14)0.3388 (4)0.0247 (11)
H5'B0.49920.24350.40160.030*
C6'B0.4515 (5)0.20517 (14)0.2599 (4)0.0243 (10)
H6'B0.52700.18530.27000.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0188 (5)0.0180 (6)0.0177 (6)0.0007 (4)0.0011 (5)0.0019 (5)
O1A0.0170 (15)0.0174 (15)0.0223 (18)0.0042 (12)0.0023 (14)0.0009 (14)
O2A0.0143 (14)0.0185 (15)0.0160 (18)0.0006 (12)0.0034 (14)0.0059 (14)
O3A0.0188 (15)0.0225 (15)0.0270 (19)0.0033 (14)0.0026 (15)0.0035 (15)
O4A0.0294 (17)0.0197 (16)0.0167 (18)0.0004 (14)0.0044 (14)0.0007 (14)
Cl1A0.0430 (7)0.0242 (6)0.0323 (7)0.0018 (5)0.0001 (6)0.0100 (6)
Cl2A0.0281 (6)0.0220 (6)0.0245 (7)0.0004 (5)0.0071 (5)0.0060 (5)
Cl3A0.0226 (6)0.0234 (6)0.0289 (7)0.0048 (5)0.0031 (5)0.0023 (5)
Cl4A0.0253 (6)0.0273 (6)0.0227 (6)0.0025 (5)0.0079 (5)0.0047 (5)
C1A0.019 (2)0.020 (2)0.016 (2)0.0015 (18)0.003 (2)0.000 (2)
C2A0.031 (3)0.018 (2)0.027 (3)0.001 (2)0.002 (2)0.007 (2)
C3A0.029 (3)0.026 (2)0.022 (3)0.001 (2)0.006 (2)0.005 (2)
C4A0.015 (2)0.013 (2)0.023 (3)0.0012 (17)0.001 (2)0.0001 (19)
C5A0.022 (2)0.020 (2)0.016 (2)0.0024 (18)0.002 (2)0.002 (2)
C6A0.017 (2)0.019 (2)0.024 (3)0.0005 (19)0.002 (2)0.002 (2)
C7A0.017 (2)0.020 (2)0.014 (2)0.0019 (19)0.0016 (19)0.002 (2)
C8A0.014 (2)0.018 (2)0.020 (3)0.0034 (18)0.002 (2)0.003 (2)
C1'A0.019 (2)0.020 (2)0.021 (3)0.0009 (19)0.001 (2)0.005 (2)
C2'A0.030 (3)0.016 (2)0.023 (2)0.0041 (19)0.003 (2)0.001 (2)
C3'A0.030 (3)0.028 (3)0.026 (3)0.004 (2)0.001 (2)0.001 (2)
C4'A0.022 (2)0.019 (2)0.023 (3)0.0030 (18)0.004 (2)0.010 (2)
C5'A0.030 (3)0.015 (2)0.035 (3)0.0022 (19)0.000 (2)0.000 (2)
C6'A0.028 (3)0.020 (2)0.029 (3)0.001 (2)0.003 (2)0.001 (2)
S1B0.0177 (5)0.0161 (5)0.0173 (6)0.0012 (4)0.0013 (5)0.0001 (5)
O1B0.0210 (15)0.0143 (15)0.0237 (19)0.0025 (13)0.0017 (14)0.0024 (14)
O2B0.0156 (15)0.0191 (16)0.0192 (19)0.0025 (12)0.0009 (15)0.0058 (14)
O3B0.0179 (15)0.0198 (15)0.0265 (18)0.0001 (13)0.0005 (15)0.0040 (15)
O4B0.0246 (16)0.0219 (17)0.0166 (18)0.0001 (14)0.0045 (14)0.0031 (15)
Cl1B0.0450 (8)0.0191 (6)0.0285 (7)0.0008 (5)0.0068 (6)0.0054 (5)
Cl2B0.0221 (5)0.0255 (6)0.0203 (6)0.0011 (5)0.0054 (5)0.0012 (5)
Cl3B0.0193 (6)0.0255 (6)0.0326 (7)0.0056 (5)0.0011 (5)0.0071 (6)
Cl4B0.0291 (6)0.0221 (6)0.0235 (6)0.0017 (5)0.0031 (5)0.0044 (5)
C1B0.021 (2)0.014 (2)0.024 (3)0.0032 (18)0.002 (2)0.003 (2)
C2B0.022 (2)0.016 (2)0.022 (3)0.0002 (19)0.002 (2)0.003 (2)
C3B0.016 (2)0.020 (2)0.031 (3)0.0001 (18)0.002 (2)0.003 (2)
C4B0.015 (2)0.016 (2)0.024 (3)0.0002 (18)0.003 (2)0.004 (2)
C5B0.026 (2)0.022 (2)0.020 (2)0.0012 (19)0.001 (2)0.003 (2)
C6B0.026 (2)0.011 (2)0.028 (3)0.0037 (19)0.003 (2)0.0006 (19)
C7B0.015 (2)0.018 (2)0.022 (3)0.0026 (19)0.002 (2)0.004 (2)
C8B0.015 (2)0.018 (2)0.019 (2)0.0035 (18)0.001 (2)0.004 (2)
C1'B0.024 (2)0.014 (2)0.019 (3)0.0047 (18)0.002 (2)0.002 (2)
C2'B0.021 (2)0.022 (2)0.029 (3)0.0005 (19)0.005 (2)0.002 (2)
C3'B0.029 (3)0.015 (2)0.026 (3)0.0048 (19)0.003 (2)0.0025 (19)
C4'B0.030 (3)0.014 (2)0.024 (3)0.0054 (19)0.013 (2)0.000 (2)
C5'B0.029 (3)0.026 (2)0.019 (2)0.011 (2)0.001 (2)0.002 (2)
C6'B0.026 (2)0.020 (2)0.027 (3)0.001 (2)0.003 (2)0.005 (2)
Geometric parameters (Å, º) top
S1A—O3A1.408 (3)S1B—O3B1.415 (3)
S1A—O4A1.415 (3)S1B—O4B1.417 (3)
S1A—O1A1.568 (3)S1B—O1B1.568 (3)
S1A—O2A1.571 (3)S1B—O2B1.571 (3)
O1A—C4A1.427 (5)O1B—C4B1.435 (5)
O2A—C7A1.459 (5)O2B—C7B1.464 (5)
Cl1A—C4'A1.759 (5)Cl1B—C4'B1.738 (5)
Cl2A—C8A1.776 (5)Cl2B—C8B1.773 (5)
Cl3A—C8A1.768 (4)Cl3B—C8B1.780 (4)
Cl4A—C8A1.765 (5)Cl4B—C8B1.764 (5)
C1A—C6A1.394 (6)C1B—C2B1.388 (6)
C1A—C2A1.400 (7)C1B—C6B1.399 (6)
C1A—C1'A1.493 (6)C1B—C1'B1.494 (6)
C2A—C3A1.383 (6)C2B—C3B1.386 (6)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.370 (6)C3B—C4B1.358 (7)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.373 (7)C4B—C5B1.377 (6)
C5A—C6A1.395 (6)C5B—C6B1.394 (6)
C5A—H5A0.9500C5B—H5B0.9500
C6A—H6A0.9500C6B—H6B0.9500
C7A—C8A1.524 (6)C7B—C8B1.499 (6)
C7A—H7A10.9900C7B—H7B10.9900
C7A—H7A20.9900C7B—H7B20.9900
C1'A—C6'A1.386 (6)C1'B—C6'B1.392 (6)
C1'A—C2'A1.406 (7)C1'B—C2'B1.416 (6)
C2'A—C3'A1.387 (6)C2'B—C3'B1.371 (6)
C2'A—H2'A0.9500C2'B—H2'B0.9500
C3'A—C4'A1.372 (6)C3'B—C4'B1.375 (7)
C3'A—H3'A0.9500C3'B—H3'B0.9500
C4'A—C5'A1.392 (7)C4'B—C5'B1.394 (6)
C5'A—C6'A1.374 (6)C5'B—C6'B1.379 (6)
C5'A—H5'A0.9500C5'B—H5'B0.9500
C6'A—H6'A0.9500C6'B—H6'B0.9500
O3A—S1A—O4A121.9 (2)O3B—S1B—O4B122.1 (2)
O3A—S1A—O1A110.81 (17)O3B—S1B—O1B110.36 (16)
O4A—S1A—O1A105.03 (18)O4B—S1B—O1B104.70 (17)
O3A—S1A—O2A104.68 (17)O3B—S1B—O2B105.19 (17)
O4A—S1A—O2A109.64 (18)O4B—S1B—O2B109.83 (18)
O1A—S1A—O2A103.31 (17)O1B—S1B—O2B103.20 (17)
C4A—O1A—S1A119.9 (3)C4B—O1B—S1B119.7 (3)
C7A—O2A—S1A116.3 (2)C7B—O2B—S1B116.5 (3)
C6A—C1A—C2A117.5 (4)C2B—C1B—C6B118.9 (4)
C6A—C1A—C1'A120.7 (4)C2B—C1B—C1'B120.4 (4)
C2A—C1A—C1'A121.7 (4)C6B—C1B—C1'B120.7 (4)
C3A—C2A—C1A121.1 (4)C3B—C2B—C1B120.4 (5)
C3A—C2A—H2A119.4C3B—C2B—H2B119.8
C1A—C2A—H2A119.4C1B—C2B—H2B119.8
C4A—C3A—C2A119.3 (4)C4B—C3B—C2B119.1 (5)
C4A—C3A—H3A120.3C4B—C3B—H3B120.5
C2A—C3A—H3A120.3C2B—C3B—H3B120.5
C3A—C4A—C5A122.0 (4)C3B—C4B—C5B123.1 (5)
C3A—C4A—O1A116.8 (4)C3B—C4B—O1B119.4 (4)
C5A—C4A—O1A120.9 (4)C5B—C4B—O1B117.4 (4)
C4A—C5A—C6A118.2 (4)C4B—C5B—C6B117.6 (4)
C4A—C5A—H5A120.9C4B—C5B—H5B121.2
C6A—C5A—H5A120.9C6B—C5B—H5B121.2
C1A—C6A—C5A121.8 (4)C5B—C6B—C1B120.8 (4)
C1A—C6A—H6A119.1C5B—C6B—H6B119.6
C5A—C6A—H6A119.1C1B—C6B—H6B119.6
O2A—C7A—C8A107.1 (3)O2B—C7B—C8B108.2 (3)
O2A—C7A—H7A1110.3O2B—C7B—H7B1110.1
C8A—C7A—H7A1110.3C8B—C7B—H7B1110.1
O2A—C7A—H7A2110.3O2B—C7B—H7B2110.1
C8A—C7A—H7A2110.3C8B—C7B—H7B2110.1
H7A1—C7A—H7A2108.5H7B1—C7B—H7B2108.4
C7A—C8A—Cl4A110.8 (3)C7B—C8B—Cl4B111.9 (3)
C7A—C8A—Cl3A105.5 (3)C7B—C8B—Cl2B110.8 (3)
Cl4A—C8A—Cl3A110.6 (3)Cl4B—C8B—Cl2B108.7 (2)
C7A—C8A—Cl2A111.2 (3)C7B—C8B—Cl3B105.9 (3)
Cl4A—C8A—Cl2A109.3 (2)Cl4B—C8B—Cl3B110.1 (2)
Cl3A—C8A—Cl2A109.5 (2)Cl2B—C8B—Cl3B109.4 (3)
C6'A—C1'A—C2'A117.9 (4)C6'B—C1'B—C2'B117.2 (4)
C6'A—C1'A—C1A121.3 (4)C6'B—C1'B—C1B121.1 (4)
C2'A—C1'A—C1A120.9 (4)C2'B—C1'B—C1B121.7 (4)
C3'A—C2'A—C1'A120.9 (4)C3'B—C2'B—C1'B121.3 (4)
C3'A—C2'A—H2'A119.5C3'B—C2'B—H2'B119.4
C1'A—C2'A—H2'A119.5C1'B—C2'B—H2'B119.4
C4'A—C3'A—C2'A119.0 (4)C2'B—C3'B—C4'B119.8 (4)
C4'A—C3'A—H3'A120.5C2'B—C3'B—H3'B120.1
C2'A—C3'A—H3'A120.5C4'B—C3'B—H3'B120.1
C3'A—C4'A—C5'A121.6 (4)C3'B—C4'B—C5'B120.8 (4)
C3'A—C4'A—Cl1A119.3 (4)C3'B—C4'B—Cl1B119.6 (4)
C5'A—C4'A—Cl1A119.1 (4)C5'B—C4'B—Cl1B119.6 (4)
C6'A—C5'A—C4'A118.5 (4)C6'B—C5'B—C4'B119.0 (4)
C6'A—C5'A—H5'A120.8C6'B—C5'B—H5'B120.5
C4'A—C5'A—H5'A120.8C4'B—C5'B—H5'B120.5
C5'A—C6'A—C1'A122.1 (5)C5'B—C6'B—C1'B121.9 (4)
C5'A—C6'A—H6'A118.9C5'B—C6'B—H6'B119.0
C1'A—C6'A—H6'A118.9C1'B—C6'B—H6'B119.0
O3A—S1A—O1A—C4A32.4 (4)O3B—S1B—O1B—C4B38.3 (4)
O4A—S1A—O1A—C4A165.9 (3)O4B—S1B—O1B—C4B171.3 (3)
O2A—S1A—O1A—C4A79.2 (3)O2B—S1B—O1B—C4B73.7 (3)
O3A—S1A—O2A—C7A176.8 (3)O3B—S1B—O2B—C7B177.1 (3)
O4A—S1A—O2A—C7A50.8 (3)O4B—S1B—O2B—C7B44.0 (4)
O1A—S1A—O2A—C7A60.8 (3)O1B—S1B—O2B—C7B67.2 (3)
C6A—C1A—C2A—C3A2.1 (7)C6B—C1B—C2B—C3B3.4 (7)
C1'A—C1A—C2A—C3A179.8 (4)C1'B—C1B—C2B—C3B176.3 (4)
C1A—C2A—C3A—C4A1.6 (7)C1B—C2B—C3B—C4B0.3 (6)
C2A—C3A—C4A—C5A0.3 (7)C2B—C3B—C4B—C5B2.3 (7)
C2A—C3A—C4A—O1A174.5 (4)C2B—C3B—C4B—O1B174.6 (4)
S1A—O1A—C4A—C3A116.3 (4)S1B—O1B—C4B—C3B90.7 (4)
S1A—O1A—C4A—C5A69.5 (5)S1B—O1B—C4B—C5B92.3 (4)
C3A—C4A—C5A—C6A1.6 (7)C3B—C4B—C5B—C6B1.6 (7)
O1A—C4A—C5A—C6A175.5 (4)O1B—C4B—C5B—C6B175.3 (4)
C2A—C1A—C6A—C5A0.8 (6)C4B—C5B—C6B—C1B1.6 (7)
C1'A—C1A—C6A—C5A179.0 (4)C2B—C1B—C6B—C5B4.0 (7)
C4A—C5A—C6A—C1A1.0 (7)C1'B—C1B—C6B—C5B175.7 (4)
S1A—O2A—C7A—C8A146.0 (3)S1B—O2B—C7B—C8B143.8 (3)
O2A—C7A—C8A—Cl4A55.9 (4)O2B—C7B—C8B—Cl4B61.5 (4)
O2A—C7A—C8A—Cl3A175.6 (3)O2B—C7B—C8B—Cl2B59.9 (4)
O2A—C7A—C8A—Cl2A65.8 (4)O2B—C7B—C8B—Cl3B178.4 (3)
C6A—C1A—C1'A—C6'A162.8 (4)C2B—C1B—C1'B—C6'B41.0 (6)
C2A—C1A—C1'A—C6'A19.1 (7)C6B—C1B—C1'B—C6'B138.6 (5)
C6A—C1A—C1'A—C2'A18.2 (6)C2B—C1B—C1'B—C2'B138.2 (5)
C2A—C1A—C1'A—C2'A159.9 (4)C6B—C1B—C1'B—C2'B42.1 (6)
C6'A—C1'A—C2'A—C3'A0.1 (7)C6'B—C1'B—C2'B—C3'B1.1 (7)
C1A—C1'A—C2'A—C3'A178.9 (4)C1B—C1'B—C2'B—C3'B179.6 (4)
C1'A—C2'A—C3'A—C4'A0.7 (7)C1'B—C2'B—C3'B—C4'B0.9 (7)
C2'A—C3'A—C4'A—C5'A2.0 (7)C2'B—C3'B—C4'B—C5'B0.8 (7)
C2'A—C3'A—C4'A—Cl1A178.0 (3)C2'B—C3'B—C4'B—Cl1B179.2 (3)
C3'A—C4'A—C5'A—C6'A2.5 (7)C3'B—C4'B—C5'B—C6'B0.9 (7)
Cl1A—C4'A—C5'A—C6'A177.6 (3)Cl1B—C4'B—C5'B—C6'B179.0 (3)
C4'A—C5'A—C6'A—C1'A1.6 (7)C4'B—C5'B—C6'B—C1'B1.2 (7)
C2'A—C1'A—C6'A—C5'A0.4 (7)C2'B—C1'B—C6'B—C5'B1.3 (7)
C1A—C1'A—C6'A—C5'A179.4 (4)C1B—C1'B—C6'B—C5'B179.5 (4)

Experimental details

Crystal data
Chemical formulaC14H10Cl4O4S
Mr416.08
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)90
a, b, c (Å)9.6305 (19), 30.273 (6), 11.330 (2)
V3)3303.3 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.86
Crystal size (mm)0.40 × 0.34 × 0.18
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.679, 0.861
No. of measured, independent and
observed [I > 2σ(I)] reflections
25566, 6476, 4862
Rint0.063
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.109, 1.05
No. of reflections6476
No. of parameters415
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.51, 0.56
Absolute structureFlack (1983), 2481 Friedel Pairs
Absolute structure parameter0.44 (7)

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELX97 (Sheldrick, 2008) and local procedures.

 

Acknowledgements

This research was supported by grants ES05605, ES012475 and ES013661 from the National Institute of Environmental Health Sciences, NIH.

References

First citationBrandao, T. A. S., Priebe, J. P., Damasceno, A. S., Bortoluzzia, A. J., Kirby, A. J. & Nome, F. (2005). J. Mol. Struct. 734, 205–209.  Web of Science CSD CrossRef CAS Google Scholar
First citationDesiraju, G. R., Paul, I. C. & Curtin, D. Y. (1979). Mol. Cryst. Liq. Cryst. 52, 259–266.  CrossRef Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHansen, L. G. (1999). The Ortho Side of PCBs. Boston: Kluwer Academic Publishers.  Google Scholar
First citationLehmler, H.-J., Robertson, L. W. & Parkin, S. (2001). Acta Cryst. E57, o590–o591.  CSD CrossRef IUCr Journals Google Scholar
First citationLehmler, H.-J., Robertson, L. W., Parkin, S. & Brock, C. P. (2002). Acta Cryst. B58, 140–147.  CSD CrossRef CAS IUCr Journals Google Scholar
First citationLetcher, 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.  Google Scholar
First citationLiu, Y., Apak, T. I., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2006). Chem. Res. Toxicol. 19, 1420–1425.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLiu, Y., Lien, I. F. F., Ruttgaizer, S., Dove, P. & Taylor, S. D. (2004). Org. Lett. 6, 209–212.  Web of Science CrossRef PubMed CAS Google Scholar
First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, 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.  Google Scholar
First citationRissanen, K., Valkonen, J. & Mannila, B. (1988a). Acta Cryst. C44, 682–684.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationRissanen, K., Valkonen, J. & Mannila, B. (1988b). Acta Cryst. C44, 684–686.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationRobertson, L. W. & Hansen, L. G. (2001). Recent Advances in the Environmental Toxicology and Health Effects of PCBs. Lexington, USA: University Press of Kentucky.  Google Scholar
First citationSacco, J. C. & James, M. O. (2005). Drug Metab. Dispos. 33, 1341–1348.  Web of Science CrossRef PubMed CAS Google Scholar
First citationShaikh, N. S., Parkin, S., Luthe, G. & Lehmler, H. J. (2008). Chemosphere, 70, 1694–1698.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTampal, N., Lehmler, H.-J., Espandiari, P., Malmberg, T. & Robertson, L. W. (2002). Chem. Res. Toxicol. 15, 1259–1266.  Web of Science CrossRef PubMed CAS Google Scholar
First citationVyas, S. M., Parkin, S. & Lehmler, H.-J. (2006). Acta Cryst. E62, o2905–o2906.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds