Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 5| May 2010| Page o1073
https://doi.org/10.1107/S1600536810012845

Bi­phenyl-4-yl 2,2,2-tri­chloro­ethyl sulfate

Xueshu Li,a Sean Parkin,b Michael W. Duffel,c Larry W. Robertsona and Hans-Joachim Lehmlera*

aDepartment of Occupational and Environmental Health, University of Iowa, 100 Oakdale Campus, 124 IREH, Iowa City, IA 52242-5000, USA, bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506-0055, USA, and cCollege of Pharmacy, Division of Medicinal and Natural Products Chemistry, University of Iowa, Iowa City, IA 52242, USA
*Correspondence e-mail: hans-joachim-lehmler@uiowa.edu

(Received 19 March 2010; accepted 6 April 2010; online 14 April 2010)

The mol­ecular structure of the title compound, C14H11Cl3O4S, displays a biphenyl dihedral angle of 4.9 (2)° between the benzene rings, which is significantly smaller than the calculated dihedral angle of 41.2° of biphenyl derivatives without ortho substituents. The CAr—O bond length of 1.432 (4) Å is comparable with other sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro­ether ester derivatives without electronegative substituents in the sulfated phenyl ring.

Related literature

For similar structures of chlorinated sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ethyl esters, see: Li et al. (2008[Li, X., Parkin, S., Robertson, L. W. & Lehmler, H.-J. (2008). Acta Cryst. E64, o2464.], 2010[Li, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010). Environ. Int. doi:10.1016/j.envint.2009.1002.1005.]). 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 information, see: Cravedi et al. (1999[Cravedi, J. P., Lafuente, A., Baradat, M., Hillenweck, A. & Perdu-Durand, E. (1999). Xenobiotica, 29, 499-509.]); 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. Heidelberg: Springer Verlag.]); Liu et al. (2006[Liu, Y., Apak, T. I., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2006). Chem. Res. Toxicol. 19, 1420-1425.], 2009[Liu, Y., Smart, J. T., Song, Y., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2009). Drug Metab. Dispos. 37, 1065-1072.]); Ohnishi et al. (2000[Ohnishi, M., Yajima, H., Takemura, T., Yamamoto, S., Mastushima, T. & Ishii, T. (2000). J. Health Sci. 46, 299-303.], 2001[Ohnishi, M., Yajima, H., Takeuchi, T., Saito, M., Yamazaki, K., Kasai, T., Nagano, K., Yamamoto, S., Matsushima, T. & Ishii, T. (2001). Toxicol. Appl. Pharmacol. 174, 122-129.]); Sacco & James (2005[Sacco, J. C. & James, M. O. (2005). Drug Metab. Dispos. 33, 1341-1348.]); Tampal et al. (2002[Tampal, N., Lehmler, H.-J., Espandiari, P., Malmberg, T. & Robertson, L. W. (2002). Chem. Res. Toxicol. 15, 1259-1266.]); Robertson & Hansen (2001[Robertson, L. W. & Hansen, L. G. (2001). Recent Advances in the Environmental Toxicology and Health Effects of PCBs. Lexington: University Press of Kentucky.]); Trotter (1961[Trotter, J. (1961). Acta Cryst. 14, 1135-1140.]); Umeda et al. (2002[Umeda, Y., Arito, H., Kano, H., Ohnishi, M., Matsumoto, M., Nagano, K., Yamamoto, S. & Matsushima, T. (2002). J. Occup. Health, 44, 176-183.], 2005[Umeda, Y., Aiso, S., Yamazaki, K., Ohnishi, M., Arito, H., Nagano, K., Yamamoto, S. & Matsushima, T. (2005). J. Vet. Med. Sci. 67, 417-424.]). For further discussion of dihedral angles in chlorinated biphenyls, see: Shaikh et al. (2008[Shaikh, N. S., Parkin, S., Luthe, G. & Lehmler, H.-J. (2008). Chemosphere, 70, 1694-1698.]).

[Scheme 1]

Experimental

Crystal data

  • C14H11Cl3O4S

  • Mr = 381.64

  • Monoclinic, P 21 /n

  • a = 7.5761 (2) Å

  • b = 5.8272 (2) Å

  • c = 35.2679 (11) Å

  • β = 90.181 (2)°

  • V = 1556.98 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.74 mm−1

  • T = 90 K

  • 0.43 × 0.40 × 0.08 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker Nonius, 2006[Bruker Nonius (2006). APEX2 and SAINT. Bruker Nonius AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.699, Tmax = 0.944

  • 15429 measured reflections

  • 3041 independent reflections

  • 1939 reflections with I > 2σ(I)

  • Rint = 0.079
Refinement

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.137

  • S = 1.09

  • 3041 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.46 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810012845/om2330sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012845/om2330Isup2.hkl

checkCIF report


Comment top

Exposure to biphenyl and structurally related chlorinated biphenyls has been associated with a range of adverse human health effects, including cancer and arteriosclerosis (Robertson & Hansen, 2001; Umeda et al., 2005, 2002; Letcher et al., 2000). Biphenyl and many lower chlorinated biphenyls are metabolized via hydroxylated biphenyl metabolites to sulfuric acid esters (Liu et al., 2006, 2009; Ohnishi et al., 2000, 2001; Sacco & James, 2005) and glucuronide conjugates (Cravedi et al., 1999; Tampal et al., 2002). While currently little is known about the toxicity of sulfate conjugates of chlorinated biphenyls, it is well established that sulfuric acid biphenyl-4-yl ester is involved in the formation of urinary calculi and, thus, plays a role in the induction of urinary bladder cancer (Ohnishi et al., 2000, 2001). Unfortunately, crystal structures of (chlorinated) sulfuric acid biphenyl-4-yl esters have not been reported, partly because of their chemical instability (Li et al., 2010). Here we report the crystal structure of a structurally related sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ether ester.

In particular the CAr—O bond length of sulfuric acid mono- and diesters may be predictive of the stability of the corresponding sulfuric acid conjugates (Brandao et al., 2005; Li et al., 2010). The CAr—O (i.e. C4—O1) bond length of the title compound is 1.432 (4) Å, which is comparable to other, chlorinated sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ether esters with no chlorine substituents in the sulfated benzene moiety (1.426 to 1.435 Å) (Li et al., 2010, 2008). In contrast, the CAr—O bond of sulfuric acid 2',3,5,5'-tetrachloro-biphenyl-4-yl ester 2,2,2-trichloro-ethyl ester, an analogous sulfuric acid diester with two chlorine substituents in the sulfated benzene moiety, is slightly shorter (1.405 (4) Å) due to the presence of the electronegative chlorine substituents (Li et al., 2010). Therefore, the sulfuric acid biphenyl-4-yl ester corresponding to the title compound is expected to be relatively stable under physiological conditions, especially compared to aromatic sulfuric acid esters with electronegative substituents in the sulfated benzene ring.

The dihedral angle of biphenyl derivatives is associated with their affinity for cellular target molecules and, therefore, can correlate with their toxicity. The title compound adopts an almost planar conformation, with a solid state dihedral angle of the biphenyl moiety of 4.9 (2)°. Similarly, the parent compound, biphenyl, adopts a planar confirmation in the solid state with a dihedral angle of 0° (Trotter, 1961). These solid state dihedral angles are significantly smaller compared to the calculated dihedral angle of 41.2° of biphenyl derivatives without ortho substituents (Shaikh et al., 2008). These deviations from the energetically most favorable conformation are most likely due to crystal packing effects, which allow the title compound to adopt an energetically less favorable conformation in the solid state by maximizing the lattice energy.

Related literature top

For similar structures of chlorinated sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ethyl esters, see: Li et al. (2008, 2010). For a review of structures of sulfuric acid aryl mono esters, see: Brandao et al. (2005). For additional background information, see: Cravedi et al. (1999); Letcher et al. (2000); Liu et al. (2006, 2009); Ohnishi et al. (2000, 2001); Sacco & James (2005); Tampal et al. (2002); Robertson & Hansen (2001); Trotter (1961); Umeda et al. (2002, 2005). For further discussion of dihedral angles in chlorinated biphenyls, see: Shaikh et al. (2008).

Experimental top

The title compound was synthesized from biphenyl-4-ol and 2,2,2-trichloroethyl sulfonyl chloride using 4-dimethylaminopyridine as catalyst (Li et al., 2008). Crystals of the title compound suitable for crystal structure analysis were obtained by slow evaporation of a solution of the title compound in methanol.

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.

Structure description top

Exposure to biphenyl and structurally related chlorinated biphenyls has been associated with a range of adverse human health effects, including cancer and arteriosclerosis (Robertson & Hansen, 2001; Umeda et al., 2005, 2002; Letcher et al., 2000). Biphenyl and many lower chlorinated biphenyls are metabolized via hydroxylated biphenyl metabolites to sulfuric acid esters (Liu et al., 2006, 2009; Ohnishi et al., 2000, 2001; Sacco & James, 2005) and glucuronide conjugates (Cravedi et al., 1999; Tampal et al., 2002). While currently little is known about the toxicity of sulfate conjugates of chlorinated biphenyls, it is well established that sulfuric acid biphenyl-4-yl ester is involved in the formation of urinary calculi and, thus, plays a role in the induction of urinary bladder cancer (Ohnishi et al., 2000, 2001). Unfortunately, crystal structures of (chlorinated) sulfuric acid biphenyl-4-yl esters have not been reported, partly because of their chemical instability (Li et al., 2010). Here we report the crystal structure of a structurally related sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ether ester.

In particular the CAr—O bond length of sulfuric acid mono- and diesters may be predictive of the stability of the corresponding sulfuric acid conjugates (Brandao et al., 2005; Li et al., 2010). The CAr—O (i.e. C4—O1) bond length of the title compound is 1.432 (4) Å, which is comparable to other, chlorinated sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ether esters with no chlorine substituents in the sulfated benzene moiety (1.426 to 1.435 Å) (Li et al., 2010, 2008). In contrast, the CAr—O bond of sulfuric acid 2',3,5,5'-tetrachloro-biphenyl-4-yl ester 2,2,2-trichloro-ethyl ester, an analogous sulfuric acid diester with two chlorine substituents in the sulfated benzene moiety, is slightly shorter (1.405 (4) Å) due to the presence of the electronegative chlorine substituents (Li et al., 2010). Therefore, the sulfuric acid biphenyl-4-yl ester corresponding to the title compound is expected to be relatively stable under physiological conditions, especially compared to aromatic sulfuric acid esters with electronegative substituents in the sulfated benzene ring.

The dihedral angle of biphenyl derivatives is associated with their affinity for cellular target molecules and, therefore, can correlate with their toxicity. The title compound adopts an almost planar conformation, with a solid state dihedral angle of the biphenyl moiety of 4.9 (2)°. Similarly, the parent compound, biphenyl, adopts a planar confirmation in the solid state with a dihedral angle of 0° (Trotter, 1961). These solid state dihedral angles are significantly smaller compared to the calculated dihedral angle of 41.2° of biphenyl derivatives without ortho substituents (Shaikh et al., 2008). These deviations from the energetically most favorable conformation are most likely due to crystal packing effects, which allow the title compound to adopt an energetically less favorable conformation in the solid state by maximizing the lattice energy.

For similar structures of chlorinated sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ethyl esters, see: Li et al. (2008, 2010). For a review of structures of sulfuric acid aryl mono esters, see: Brandao et al. (2005). For additional background information, see: Cravedi et al. (1999); Letcher et al. (2000); Liu et al. (2006, 2009); Ohnishi et al. (2000, 2001); Sacco & James (2005); Tampal et al. (2002); Robertson & Hansen (2001); Trotter (1961); Umeda et al. (2002, 2005). For further discussion of dihedral angles in chlorinated biphenyls, see: Shaikh et al. (2008).

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-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Biphenyl-4-yl 2,2,2-trichloroethyl sulfate top
Crystal data top
C14H11Cl3O4SF(000) = 776
Mr = 381.64Dx = 1.628 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 19102 reflections
a = 7.5761 (2) Åθ = 1.0–27.5°
b = 5.8272 (2) ŵ = 0.74 mm−1
c = 35.2679 (11) ÅT = 90 K
β = 90.181 (2)°Slab, colourless
V = 1556.98 (8) Å30.43 × 0.40 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer		3041 independent reflections
Radiation source: fine-focus sealed tube1939 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
Detector resolution: 18 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scans at fixed χ = 55°h = −9→9
Absorption correction: multi-scan
(SADABS; Bruker Nonius, 2006)		k = −7→7
Tmin = 0.699, Tmax = 0.944l = −43→43
15429 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0617P)2 + 1.446P]
where P = (Fo2 + 2Fc2)/3
3041 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.62 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
C14H11Cl3O4SV = 1556.98 (8) Å3
Mr = 381.64Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.5761 (2) ŵ = 0.74 mm−1
b = 5.8272 (2) ÅT = 90 K
c = 35.2679 (11) Å0.43 × 0.40 × 0.08 mm
β = 90.181 (2)°
Data collection top
Nonius KappaCCD
diffractometer		3041 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker Nonius, 2006)		1939 reflections with I > 2σ(I)
Tmin = 0.699, Tmax = 0.944Rint = 0.079
15429 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.09Δρmax = 0.62 e Å−3
3041 reflectionsΔρmin = −0.46 e Å−3
199 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.57446 (13)0.92450 (18)0.59262 (3)0.0208 (3)
O10.6710 (3)0.7616 (5)0.62196 (7)0.0220 (7)
O20.3875 (3)0.8117 (5)0.58864 (7)0.0209 (6)
O30.6713 (4)0.8999 (5)0.55880 (7)0.0261 (7)
O40.5421 (4)1.1419 (5)0.60895 (7)0.0261 (7)
Cl10.21565 (14)0.28054 (18)0.52992 (3)0.0281 (3)
Cl20.03163 (13)0.6724 (2)0.56132 (3)0.0289 (3)
Cl30.29160 (14)0.73955 (18)0.50317 (3)0.0260 (3)
C10.5167 (5)0.7417 (7)0.73623 (11)0.0193 (9)
C20.4726 (5)0.5655 (7)0.71089 (11)0.0234 (10)
H20.40870.43650.71990.028*
C30.5198 (6)0.5746 (7)0.67315 (10)0.0248 (10)
H30.48880.45390.65630.030*
C40.6121 (5)0.7612 (7)0.66051 (10)0.0192 (9)
C50.6597 (5)0.9377 (8)0.68381 (11)0.0262 (10)
H50.72431.06500.67430.031*
C60.6116 (5)0.9270 (7)0.72177 (11)0.0242 (10)
H60.64411.04890.73830.029*
C70.3776 (5)0.5798 (7)0.57323 (10)0.0202 (9)
H7A0.34970.46960.59370.024*
H7B0.49280.53640.56210.024*
C80.2351 (5)0.5715 (7)0.54294 (10)0.0203 (9)
C1'0.4713 (5)0.7278 (7)0.77748 (10)0.0188 (9)
C2'0.5201 (6)0.9018 (7)0.80282 (11)0.0268 (10)
H2'0.57731.03520.79340.032*
C3'0.4867 (6)0.8833 (8)0.84125 (12)0.0304 (11)
H3'0.52191.00330.85790.037*
C4'0.4027 (5)0.6923 (8)0.85568 (11)0.0265 (10)
H4'0.38110.67880.88210.032*
C5'0.3503 (6)0.5199 (8)0.83080 (11)0.0330 (11)
H5'0.29030.38870.84020.040*
C6'0.3851 (5)0.5385 (8)0.79256 (11)0.0305 (11)
H6'0.34890.41840.77610.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0235 (6)0.0200 (6)0.0188 (5)0.0022 (5)−0.0014 (4)0.0011 (4)
O10.0250 (16)0.0222 (17)0.0187 (14)0.0051 (13)−0.0025 (12)0.0031 (12)
O20.0179 (15)0.0206 (16)0.0242 (15)0.0040 (13)−0.0021 (11)−0.0042 (12)
O30.0283 (16)0.0268 (18)0.0232 (14)0.0012 (14)0.0034 (12)0.0018 (13)
O40.0368 (17)0.0170 (16)0.0245 (15)0.0058 (14)−0.0058 (13)−0.0071 (13)
Cl10.0364 (6)0.0211 (6)0.0267 (5)−0.0025 (5)−0.0040 (5)−0.0021 (4)
Cl20.0223 (6)0.0371 (7)0.0274 (6)0.0027 (5)0.0009 (4)−0.0017 (5)
Cl30.0353 (6)0.0243 (6)0.0186 (5)−0.0011 (5)0.0026 (4)0.0022 (4)
C10.014 (2)0.021 (2)0.023 (2)0.0037 (18)−0.0018 (16)0.0023 (18)
C20.032 (2)0.011 (2)0.027 (2)−0.0016 (19)−0.0028 (18)0.0027 (18)
C30.038 (3)0.018 (2)0.019 (2)−0.004 (2)−0.0042 (19)0.0019 (18)
C40.018 (2)0.022 (2)0.0171 (19)0.0096 (18)−0.0041 (16)−0.0004 (18)
C50.024 (2)0.029 (3)0.026 (2)−0.009 (2)−0.0031 (18)0.0021 (19)
C60.022 (2)0.026 (3)0.024 (2)−0.0067 (19)−0.0041 (17)−0.0071 (19)
C70.028 (2)0.015 (2)0.0177 (19)0.0027 (18)−0.0002 (17)−0.0003 (16)
C80.024 (2)0.016 (2)0.021 (2)0.0034 (18)0.0002 (17)−0.0008 (17)
C1'0.016 (2)0.018 (2)0.022 (2)−0.0012 (18)−0.0009 (16)−0.0024 (17)
C2'0.034 (3)0.022 (3)0.024 (2)−0.003 (2)0.0029 (19)0.0009 (19)
C3'0.037 (3)0.030 (3)0.024 (2)−0.004 (2)0.005 (2)−0.006 (2)
C4'0.026 (2)0.034 (3)0.019 (2)0.005 (2)0.0074 (18)−0.0019 (19)
C5'0.043 (3)0.030 (3)0.026 (2)−0.013 (2)0.012 (2)−0.001 (2)
C6'0.031 (3)0.031 (3)0.030 (2)−0.009 (2)0.006 (2)−0.008 (2)
Geometric parameters (Å, º) top
S1—O31.410 (3)C5—C61.390 (5)
S1—O41.414 (3)C5—H50.9500
S1—O21.567 (3)C6—H60.9500
S1—O11.582 (3)C7—C81.518 (5)
O1—C41.432 (4)C7—H7A0.9900
O2—C71.459 (5)C7—H7B0.9900
Cl1—C81.762 (4)C1'—C6'1.389 (6)
Cl2—C81.774 (4)C1'—C2'1.400 (5)
Cl3—C81.765 (4)C2'—C3'1.384 (5)
C1—C61.395 (6)C2'—H2'0.9500
C1—C21.401 (5)C3'—C4'1.380 (6)
C1—C1'1.498 (5)C3'—H3'0.9500
C2—C31.380 (5)C4'—C5'1.391 (6)
C2—H20.9500C4'—H4'0.9500
C3—C41.368 (6)C5'—C6'1.379 (5)
C3—H30.9500C5'—H5'0.9500
C4—C51.364 (5)C6'—H6'0.9500
O3—S1—O4121.83 (18)C8—C7—H7A109.9
O3—S1—O2110.75 (16)O2—C7—H7B109.9
O4—S1—O2104.74 (16)C8—C7—H7B109.9
O3—S1—O1104.57 (16)H7A—C7—H7B108.3
O4—S1—O1110.58 (15)C7—C8—Cl1105.8 (3)
O2—S1—O1102.89 (15)C7—C8—Cl3111.6 (3)
C4—O1—S1118.5 (2)Cl1—C8—Cl3110.3 (2)
C7—O2—S1117.8 (2)C7—C8—Cl2110.5 (3)
C6—C1—C2117.1 (4)Cl1—C8—Cl2110.0 (2)
C6—C1—C1'121.1 (4)Cl3—C8—Cl2108.6 (2)
C2—C1—C1'121.7 (4)C6'—C1'—C2'117.0 (4)
C3—C2—C1121.7 (4)C6'—C1'—C1121.6 (4)
C3—C2—H2119.2C2'—C1'—C1121.3 (4)
C1—C2—H2119.2C3'—C2'—C1'121.3 (4)
C4—C3—C2118.6 (4)C3'—C2'—H2'119.3
C4—C3—H3120.7C1'—C2'—H2'119.3
C2—C3—H3120.7C4'—C3'—C2'120.7 (4)
C5—C4—C3122.5 (4)C4'—C3'—H3'119.7
C5—C4—O1119.2 (4)C2'—C3'—H3'119.7
C3—C4—O1118.2 (3)C3'—C4'—C5'118.7 (4)
C4—C5—C6118.5 (4)C3'—C4'—H4'120.6
C4—C5—H5120.8C5'—C4'—H4'120.6
C6—C5—H5120.8C6'—C5'—C4'120.4 (4)
C5—C6—C1121.6 (4)C6'—C5'—H5'119.8
C5—C6—H6119.2C4'—C5'—H5'119.8
C1—C6—H6119.2C5'—C6'—C1'121.9 (4)
O2—C7—C8109.1 (3)C5'—C6'—H6'119.1
O2—C7—H7A109.9C1'—C6'—H6'119.1
O3—S1—O1—C4175.2 (3)C1'—C1—C6—C5177.7 (4)
O4—S1—O1—C442.4 (3)S1—O2—C7—C8−132.5 (3)
O2—S1—O1—C4−69.0 (3)O2—C7—C8—Cl1−173.5 (2)
O3—S1—O2—C748.4 (3)O2—C7—C8—Cl366.5 (3)
O4—S1—O2—C7−178.5 (2)O2—C7—C8—Cl2−54.5 (4)
O1—S1—O2—C7−62.8 (3)C6—C1—C1'—C6'−176.6 (4)
C6—C1—C2—C3−0.4 (6)C2—C1—C1'—C6'0.7 (6)
C1'—C1—C2—C3−177.7 (4)C6—C1—C1'—C2'1.0 (6)
C1—C2—C3—C40.1 (6)C2—C1—C1'—C2'178.2 (4)
C2—C3—C4—C50.3 (6)C6'—C1'—C2'—C3'1.2 (6)
C2—C3—C4—O1175.7 (3)C1—C1'—C2'—C3'−176.4 (4)
S1—O1—C4—C5−77.2 (4)C1'—C2'—C3'—C4'−0.5 (7)
S1—O1—C4—C3107.2 (4)C2'—C3'—C4'—C5'−0.8 (7)
C3—C4—C5—C6−0.3 (6)C3'—C4'—C5'—C6'1.2 (7)
O1—C4—C5—C6−175.7 (3)C4'—C5'—C6'—C1'−0.5 (7)
C4—C5—C6—C1−0.1 (6)C2'—C1'—C6'—C5'−0.8 (6)
C2—C1—C6—C50.4 (6)C1—C1'—C6'—C5'176.9 (4)

Experimental details

Crystal data
Chemical formulaC14H11Cl3O4S
Mr381.64
Crystal system, space groupMonoclinic, P21/n
Temperature (K)90
a, b, c (Å)7.5761 (2), 5.8272 (2), 35.2679 (11)
β (°) 90.181 (2)
V (Å3)1556.98 (8)
Z4
Radiation typeMo Kα
µ (mm−1)0.74
Crystal size (mm)0.43 × 0.40 × 0.08
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker Nonius, 2006)
Tmin, Tmax0.699, 0.944
No. of measured, independent and
observed [I > 2σ(I)] reflections		15429, 3041, 1939
Rint0.079
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.137, 1.09
No. of reflections3041
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.62, −0.46

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 grant Nos. 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 citationBruker Nonius (2006). APEX2 and SAINT. Bruker Nonius AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCravedi, J. P., Lafuente, A., Baradat, M., Hillenweck, A. & Perdu-Durand, E. (1999). Xenobiotica, 29, 499–509.  Web of Science CrossRef PubMed CAS 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. Heidelberg: Springer Verlag.  Google Scholar
 First citationLi, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010). Environ. Int. doi:10.1016/j.envint.2009.1002.1005.  Google Scholar
 First citationLi, X., Parkin, S., Robertson, L. W. & Lehmler, H.-J. (2008). Acta Cryst. E64, o2464.  Web of Science CrossRef IUCr Journals 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., Smart, J. T., Song, Y., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2009). Drug Metab. Dispos. 37, 1065–1072.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOhnishi, M., Yajima, H., Takemura, T., Yamamoto, S., Mastushima, T. & Ishii, T. (2000). J. Health Sci. 46, 299–303.  CrossRef CAS Google Scholar
 First citationOhnishi, M., Yajima, H., Takeuchi, T., Saito, M., Yamazaki, K., Kasai, T., Nagano, K., Yamamoto, S., Matsushima, T. & Ishii, T. (2001). Toxicol. Appl. Pharmacol. 174, 122–129.  Web of Science CrossRef PubMed CAS 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 citationRobertson, L. W. & Hansen, L. G. (2001). Recent Advances in the Environmental Toxicology and Health Effects of PCBs. Lexington: 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 citationTrotter, J. (1961). Acta Cryst. 14, 1135–1140.  CSD CrossRef IUCr Journals Web of Science Google Scholar
 First citationUmeda, Y., Aiso, S., Yamazaki, K., Ohnishi, M., Arito, H., Nagano, K., Yamamoto, S. & Matsushima, T. (2005). J. Vet. Med. Sci. 67, 417–424.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationUmeda, Y., Arito, H., Kano, H., Ohnishi, M., Matsumoto, M., Nagano, K., Yamamoto, S. & Matsushima, T. (2002). J. Occup. Health, 44, 176–183.  Web of Science CrossRef CAS 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
Volume 66| Part 5| May 2010| Page o1073
https://doi.org/10.1107/S1600536810012845
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS