Literature DB >> 21579128

Biphenyl-4-yl 2,2,2-trichloro-ethyl sulfate.

Xueshu Li, Sean Parkin, Michael W Duffel, Larry W Robertson, Hans-Joachim Lehmler.

Abstract

The mol-ecular structure of the title compound, C(14)H(11)Cl(3)O(4)S, 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 C(Ar)-O bond length of 1.432 (4) Å is comparable with other sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ether ester derivatives without electronegative substituents in the sulfated phenyl ring.

Entities: Chemical Disease Species

Year: 2010 PMID： 21579128 PMCID： PMC2979148 DOI： 10.1107/S1600536810012845

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

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

Crystal data

C14H11Cl3O4S M = 381.64 Monoclinic, 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 ▶) T min = 0.699, T max = 0.944 15429 measured reflections 3041 independent reflections 1939 reflections with I > 2σ(I) R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 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 ▶); 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. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012845/om2330sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012845/om2330Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₁Cl₃O₄S	F(000) = 776
M_r = 381.64	D_x = 1.628 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19102 reflections
a = 7.5761 (2) Å	θ = 1.0–27.5°
b = 5.8272 (2) Å	µ = 0.74 mm⁻¹
c = 35.2679 (11) Å	T = 90 K
β = 90.181 (2)°	Slab, colourless
V = 1556.98 (8) Å³	0.43 × 0.40 × 0.08 mm
Z = 4

Nonius KappaCCD diffractometer	3041 independent reflections
Radiation source: fine-focus sealed tube	1939 reflections with I > 2σ(I)
graphite	R_int = 0.079
Detector resolution: 18 pixels mm^-1	θ_max = 26.0°, θ_min = 2.3°
ω scans at fixed χ = 55°	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker Nonius, 2006)	k = −7→7
T_min = 0.699, T_max = 0.944	l = −43→43
15429 measured reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0617P)² + 1.446P] where P = (F_o² + 2F_c²)/3
3041 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
S1	0.57446 (13)	0.92450 (18)	0.59262 (3)	0.0208 (3)
O1	0.6710 (3)	0.7616 (5)	0.62196 (7)	0.0220 (7)
O2	0.3875 (3)	0.8117 (5)	0.58864 (7)	0.0209 (6)
O3	0.6713 (4)	0.8999 (5)	0.55880 (7)	0.0261 (7)
O4	0.5421 (4)	1.1419 (5)	0.60895 (7)	0.0261 (7)
Cl1	0.21565 (14)	0.28054 (18)	0.52992 (3)	0.0281 (3)
Cl2	0.03163 (13)	0.6724 (2)	0.56132 (3)	0.0289 (3)
Cl3	0.29160 (14)	0.73955 (18)	0.50317 (3)	0.0260 (3)
C1	0.5167 (5)	0.7417 (7)	0.73623 (11)	0.0193 (9)
C2	0.4726 (5)	0.5655 (7)	0.71089 (11)	0.0234 (10)
H2	0.4087	0.4365	0.7199	0.028*
C3	0.5198 (6)	0.5746 (7)	0.67315 (10)	0.0248 (10)
H3	0.4888	0.4539	0.6563	0.030*
C4	0.6121 (5)	0.7612 (7)	0.66051 (10)	0.0192 (9)
C5	0.6597 (5)	0.9377 (8)	0.68381 (11)	0.0262 (10)
H5	0.7243	1.0650	0.6743	0.031*
C6	0.6116 (5)	0.9270 (7)	0.72177 (11)	0.0242 (10)
H6	0.6441	1.0489	0.7383	0.029*
C7	0.3776 (5)	0.5798 (7)	0.57323 (10)	0.0202 (9)
H7A	0.3497	0.4696	0.5937	0.024*
H7B	0.4928	0.5364	0.5621	0.024*
C8	0.2351 (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'	0.5773	1.0352	0.7934	0.032*
C3'	0.4867 (6)	0.8833 (8)	0.84125 (12)	0.0304 (11)
H3'	0.5219	1.0033	0.8579	0.037*
C4'	0.4027 (5)	0.6923 (8)	0.85568 (11)	0.0265 (10)
H4'	0.3811	0.6788	0.8821	0.032*
C5'	0.3503 (6)	0.5199 (8)	0.83080 (11)	0.0330 (11)
H5'	0.2903	0.3887	0.8402	0.040*
C6'	0.3851 (5)	0.5385 (8)	0.79256 (11)	0.0305 (11)
H6'	0.3489	0.4184	0.7761	0.037*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0235 (6)	0.0200 (6)	0.0188 (5)	0.0022 (5)	−0.0014 (4)	0.0011 (4)
O1	0.0250 (16)	0.0222 (17)	0.0187 (14)	0.0051 (13)	−0.0025 (12)	0.0031 (12)
O2	0.0179 (15)	0.0206 (16)	0.0242 (15)	0.0040 (13)	−0.0021 (11)	−0.0042 (12)
O3	0.0283 (16)	0.0268 (18)	0.0232 (14)	0.0012 (14)	0.0034 (12)	0.0018 (13)
O4	0.0368 (17)	0.0170 (16)	0.0245 (15)	0.0058 (14)	−0.0058 (13)	−0.0071 (13)
Cl1	0.0364 (6)	0.0211 (6)	0.0267 (5)	−0.0025 (5)	−0.0040 (5)	−0.0021 (4)
Cl2	0.0223 (6)	0.0371 (7)	0.0274 (6)	0.0027 (5)	0.0009 (4)	−0.0017 (5)
Cl3	0.0353 (6)	0.0243 (6)	0.0186 (5)	−0.0011 (5)	0.0026 (4)	0.0022 (4)
C1	0.014 (2)	0.021 (2)	0.023 (2)	0.0037 (18)	−0.0018 (16)	0.0023 (18)
C2	0.032 (2)	0.011 (2)	0.027 (2)	−0.0016 (19)	−0.0028 (18)	0.0027 (18)
C3	0.038 (3)	0.018 (2)	0.019 (2)	−0.004 (2)	−0.0042 (19)	0.0019 (18)
C4	0.018 (2)	0.022 (2)	0.0171 (19)	0.0096 (18)	−0.0041 (16)	−0.0004 (18)
C5	0.024 (2)	0.029 (3)	0.026 (2)	−0.009 (2)	−0.0031 (18)	0.0021 (19)
C6	0.022 (2)	0.026 (3)	0.024 (2)	−0.0067 (19)	−0.0041 (17)	−0.0071 (19)
C7	0.028 (2)	0.015 (2)	0.0177 (19)	0.0027 (18)	−0.0002 (17)	−0.0003 (16)
C8	0.024 (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)

S1—O3	1.410 (3)	C5—C6	1.390 (5)
S1—O4	1.414 (3)	C5—H5	0.9500
S1—O2	1.567 (3)	C6—H6	0.9500
S1—O1	1.582 (3)	C7—C8	1.518 (5)
O1—C4	1.432 (4)	C7—H7A	0.9900
O2—C7	1.459 (5)	C7—H7B	0.9900
Cl1—C8	1.762 (4)	C1'—C6'	1.389 (6)
Cl2—C8	1.774 (4)	C1'—C2'	1.400 (5)
Cl3—C8	1.765 (4)	C2'—C3'	1.384 (5)
C1—C6	1.395 (6)	C2'—H2'	0.9500
C1—C2	1.401 (5)	C3'—C4'	1.380 (6)
C1—C1'	1.498 (5)	C3'—H3'	0.9500
C2—C3	1.380 (5)	C4'—C5'	1.391 (6)
C2—H2	0.9500	C4'—H4'	0.9500
C3—C4	1.368 (6)	C5'—C6'	1.379 (5)
C3—H3	0.9500	C5'—H5'	0.9500
C4—C5	1.364 (5)	C6'—H6'	0.9500

O3—S1—O4	121.83 (18)	C8—C7—H7A	109.9
O3—S1—O2	110.75 (16)	O2—C7—H7B	109.9
O4—S1—O2	104.74 (16)	C8—C7—H7B	109.9
O3—S1—O1	104.57 (16)	H7A—C7—H7B	108.3
O4—S1—O1	110.58 (15)	C7—C8—Cl1	105.8 (3)
O2—S1—O1	102.89 (15)	C7—C8—Cl3	111.6 (3)
C4—O1—S1	118.5 (2)	Cl1—C8—Cl3	110.3 (2)
C7—O2—S1	117.8 (2)	C7—C8—Cl2	110.5 (3)
C6—C1—C2	117.1 (4)	Cl1—C8—Cl2	110.0 (2)
C6—C1—C1'	121.1 (4)	Cl3—C8—Cl2	108.6 (2)
C2—C1—C1'	121.7 (4)	C6'—C1'—C2'	117.0 (4)
C3—C2—C1	121.7 (4)	C6'—C1'—C1	121.6 (4)
C3—C2—H2	119.2	C2'—C1'—C1	121.3 (4)
C1—C2—H2	119.2	C3'—C2'—C1'	121.3 (4)
C4—C3—C2	118.6 (4)	C3'—C2'—H2'	119.3
C4—C3—H3	120.7	C1'—C2'—H2'	119.3
C2—C3—H3	120.7	C4'—C3'—C2'	120.7 (4)
C5—C4—C3	122.5 (4)	C4'—C3'—H3'	119.7
C5—C4—O1	119.2 (4)	C2'—C3'—H3'	119.7
C3—C4—O1	118.2 (3)	C3'—C4'—C5'	118.7 (4)
C4—C5—C6	118.5 (4)	C3'—C4'—H4'	120.6
C4—C5—H5	120.8	C5'—C4'—H4'	120.6
C6—C5—H5	120.8	C6'—C5'—C4'	120.4 (4)
C5—C6—C1	121.6 (4)	C6'—C5'—H5'	119.8
C5—C6—H6	119.2	C4'—C5'—H5'	119.8
C1—C6—H6	119.2	C5'—C6'—C1'	121.9 (4)
O2—C7—C8	109.1 (3)	C5'—C6'—H6'	119.1
O2—C7—H7A	109.9	C1'—C6'—H6'	119.1

O3—S1—O1—C4	175.2 (3)	C1'—C1—C6—C5	177.7 (4)
O4—S1—O1—C4	42.4 (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—C7	48.4 (3)	O2—C7—C8—Cl3	66.5 (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—C4	0.1 (6)	C2—C1—C1'—C2'	178.2 (4)
C2—C3—C4—C5	0.3 (6)	C6'—C1'—C2'—C3'	1.2 (6)
C2—C3—C4—O1	175.7 (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—C3	107.2 (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—C5	0.4 (6)	C1—C1'—C6'—C5'	176.9 (4)

11 in total

1. Mechanism of urinary tract crystal formation following biphenyl treatment.

Authors: M Ohnishi; H Yajima; T Takeuchi; M Saito; K Yamazaki; T Kasai; K Nagano; S Yamamoto; T Matsushima; T Ishii
Journal: Toxicol Appl Pharmacol Date: 2001-07-15 Impact factor: 4.219

2. Carcinogenicity of biphenyl in mice by two years feeding.

Authors: Yumi Umeda; Shigetoshi Aiso; Kazunori Yamazaki; Makoto Ohnishi; Heihachiro Arito; Kasuke Nagano; Seigo Yamamoto; Taijiro Matsushima
Journal: J Vet Med Sci Date: 2005-04 Impact factor: 1.267

3. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

4. Sulfonation of environmental chemicals and their metabolites in the polar bear (Ursus maritimus).

Authors: James C Sacco; Margaret O James
Journal: Drug Metab Dispos Date: 2005-06-10 Impact factor: 3.922

5. Glucuronidation of hydroxylated polychlorinated biphenyls (PCBs).

Authors: Nilufer Tampal; Hans-Joachim Lehmler; Parvaneh Espandiari; Tina Malmberg; Larry W Robertson
Journal: Chem Res Toxicol Date: 2002-10 Impact factor: 3.739

6. Biotransformation of pentachlorophenol, aniline and biphenyl in isolated rainbow trout (Oncorhynchus mykiss) hepatocytes: comparison with in vivo metabolism.

Authors: J P Cravedi; A Lafuente; M Baradat; A Hillenweck; E Perdu-Durand
Journal: Xenobiotica Date: 1999-05 Impact factor: 1.908

7. The three-dimensional structure of 3,3',4,4'-tetrachlorobiphenyl, a dioxin-like polychlorinated biphenyl (PCB).

Authors: Nadim S Shaikh; Sean Parkin; Gregor Luthe; Hans-Joachim Lehmler
Journal: Chemosphere Date: 2007-08-27 Impact factor: 7.086

8. An efficient approach to sulfate metabolites of polychlorinated biphenyls.

Authors: Xueshu Li; Sean Parkin; Michael W Duffel; Larry W Robertson; Hans-Joachim Lehmler
Journal: Environ Int Date: 2009-04-05 Impact factor: 9.621

9. Structure-activity relationships for hydroxylated polychlorinated biphenyls as substrates and inhibitors of rat sulfotransferases and modification of these relationships by changes in thiol status.

Authors: Yungang Liu; Jason T Smart; Yang Song; Hans-Joachim Lehmler; Larry W Robertson; Michael W Duffel
Journal: Drug Metab Dispos Date: 2009-02-05 Impact factor: 3.922