4'-Chloro-biphenyl-3-yl 2,2,2-trichloro-ethyl sulfate.

The title compound, C(14)H(10)Cl(4)O(4)S, is a 2,2,2-trichloro-ethyl-protected precursor of 4'-chloro-biphenyl-3-yl sulfate, a sulfuric acid ester of 4'-chloro-biphenyl-3-ol. The C(aromatic)-O and O-S bond lengths of the C(aromatic)-O-S unit are comparable to those in structurally analogous biphenyl-4-yl 2,2,2-trichloro-ethyl sulfates with no electro-negative chlorine substituent in the benzene ring with the sulfate ester group. The dihedral angle between the aromatic rings is 27.47 (6)°.

Related literature

For similar structures of sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ethyl esters, see: Li et al. (2008 ▶, 2010a ▶,b ▶,c ▶). For a review of 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 to hy­droxy­lated polychlorinated biphenyls, see: Bergman et al. (1994 ▶); Buckman et al. (2006 ▶); Dirtu et al. (2010 ▶); Liu et al. (2006 ▶, 2009 ▶); Nomiyama et al. (2010 ▶); Wang et al. (2006 ▶).

Experimental

Crystal data

C14H10Cl4O4S

M = 416.08

Monoclinic,

a = 21.1900 (3) Å

b = 5.8543 (1) Å

c = 26.6803 (5) Å

β = 98.304 (1)°

V = 3275.06 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.87 mm−1

T = 90 K

0.41 × 0.22 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.718, T max = 0.950

30021 measured reflections

3759 independent reflections

3242 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.067

S = 1.05

3759 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.38 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/S1600536810031338/om2350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031338/om2350Isup2.hkl

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

C14H10Cl4O4S	F(000) = 1680
Mr = 416.08	Dx = 1.688 Mg m−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2ya	Cell parameters from 4127 reflections
a = 21.1900 (3) Å	θ = 1.0–27.5°
b = 5.8543 (1) Å	µ = 0.87 mm−1
c = 26.6803 (5) Å	T = 90 K
β = 98.304 (1)°	Plate, colourless
V = 3275.06 (10) Å3	0.41 × 0.22 × 0.06 mm
Z = 8

Nonius KappaCCD diffractometer	3759 independent reflections
Radiation source: fine-focus sealed tube	3242 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 18 pixels mm-1	θmax = 27.5°, θmin = 1.5°
ω scans at fixed χ = 55°	h = −27→27
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −7→7
Tmin = 0.718, Tmax = 0.950	l = −34→34
30021 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0294P)2 + 3.9224P] where P = (Fo2 + 2Fc2)/3
3759 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.205499 (17)	0.54226 (7)	0.300571 (14)	0.01597 (9)
O1	0.18726 (5)	0.4208 (2)	0.24808 (4)	0.0172 (2)
O2	0.19895 (5)	0.3440 (2)	0.33919 (4)	0.0183 (2)
O3	0.15849 (5)	0.7045 (2)	0.30865 (4)	0.0221 (2)
O4	0.27060 (5)	0.6040 (2)	0.30274 (4)	0.0248 (3)
Cl1	−0.064775 (19)	1.32997 (7)	0.026719 (15)	0.02388 (10)
Cl2	0.279773 (19)	0.45519 (7)	0.437358 (15)	0.02180 (10)
Cl3	0.333188 (17)	0.00690 (7)	0.427046 (15)	0.02125 (10)
Cl4	0.199083 (17)	0.05436 (7)	0.434813 (14)	0.01980 (10)
C1	0.01131 (7)	0.7573 (3)	0.13260 (5)	0.0141 (3)
C2	−0.05371 (7)	0.8102 (3)	0.12421 (6)	0.0169 (3)
H2	−0.0823	0.7255	0.1414	0.020*
C3	−0.07744 (7)	0.9834 (3)	0.09145 (6)	0.0182 (3)
H3	−0.1217	1.0176	0.0863	0.022*
C4	−0.03566 (7)	1.1058 (3)	0.06635 (6)	0.0173 (3)
C5	0.02901 (7)	1.0572 (3)	0.07324 (6)	0.0179 (3)
H5	0.0571	1.1412	0.0555	0.021*
C6	0.05201 (7)	0.8843 (3)	0.10634 (6)	0.0169 (3)
H6	0.0964	0.8512	0.1114	0.020*
C1'	0.03627 (7)	0.5740 (3)	0.16854 (5)	0.0139 (3)
C2'	0.09909 (7)	0.5839 (3)	0.19354 (5)	0.0147 (3)
H2'	0.1259	0.7090	0.1881	0.018*
C3'	0.12148 (7)	0.4097 (3)	0.22605 (5)	0.0150 (3)
C4'	0.08533 (7)	0.2238 (3)	0.23630 (6)	0.0169 (3)
H4'	0.1025	0.1062	0.2588	0.020*
C5'	0.02240 (7)	0.2170 (3)	0.21209 (6)	0.0175 (3)
H5'	−0.0044	0.0935	0.2186	0.021*
C6'	−0.00152 (7)	0.3877 (3)	0.17880 (5)	0.0155 (3)
H6'	−0.0444	0.3785	0.1625	0.019*
C7	0.25272 (7)	0.1927 (3)	0.35354 (6)	0.0166 (3)
H7A	0.2910	0.2522	0.3406	0.020*
H7B	0.2431	0.0387	0.3391	0.020*
C8	0.26470 (7)	0.1800 (3)	0.41106 (6)	0.0153 (3)

	U11	U22	U33	U12	U13	U23
S1	0.01324 (17)	0.0176 (2)	0.01656 (19)	−0.00114 (14)	0.00035 (13)	0.00386 (14)
O1	0.0119 (5)	0.0242 (6)	0.0157 (5)	0.0030 (4)	0.0023 (4)	0.0016 (5)
O2	0.0130 (5)	0.0241 (6)	0.0179 (5)	0.0007 (4)	0.0025 (4)	0.0087 (5)
O3	0.0221 (6)	0.0204 (6)	0.0228 (6)	0.0036 (5)	0.0000 (4)	−0.0015 (5)
O4	0.0158 (5)	0.0291 (7)	0.0282 (6)	−0.0073 (5)	−0.0011 (4)	0.0095 (5)
Cl1	0.0251 (2)	0.0248 (2)	0.0220 (2)	0.00861 (17)	0.00412 (15)	0.00689 (16)
Cl2	0.0263 (2)	0.0171 (2)	0.0219 (2)	−0.00104 (15)	0.00333 (15)	−0.00356 (15)
Cl3	0.01544 (17)	0.0210 (2)	0.0267 (2)	0.00532 (15)	0.00114 (14)	0.00543 (16)
Cl4	0.01582 (17)	0.0237 (2)	0.02059 (19)	−0.00115 (15)	0.00512 (14)	0.00656 (15)
C1	0.0139 (7)	0.0161 (7)	0.0124 (7)	−0.0002 (6)	0.0017 (5)	−0.0024 (6)
C2	0.0122 (7)	0.0210 (8)	0.0178 (7)	−0.0024 (6)	0.0032 (5)	−0.0008 (6)
C3	0.0115 (7)	0.0231 (8)	0.0196 (8)	0.0011 (6)	0.0003 (6)	−0.0021 (6)
C4	0.0196 (7)	0.0177 (8)	0.0137 (7)	0.0047 (6)	0.0000 (6)	0.0007 (6)
C5	0.0179 (7)	0.0195 (8)	0.0175 (8)	−0.0004 (6)	0.0066 (6)	0.0017 (6)
C6	0.0120 (7)	0.0203 (8)	0.0190 (7)	0.0020 (6)	0.0048 (5)	−0.0003 (6)
C1'	0.0127 (6)	0.0173 (8)	0.0123 (7)	0.0005 (6)	0.0034 (5)	−0.0017 (6)
C2'	0.0132 (7)	0.0170 (8)	0.0149 (7)	−0.0011 (6)	0.0050 (5)	−0.0005 (6)
C3'	0.0109 (6)	0.0199 (8)	0.0144 (7)	0.0023 (6)	0.0027 (5)	−0.0021 (6)
C4'	0.0213 (7)	0.0158 (8)	0.0143 (7)	0.0018 (6)	0.0051 (6)	0.0006 (6)
C5'	0.0215 (8)	0.0166 (8)	0.0155 (7)	−0.0053 (6)	0.0067 (6)	−0.0028 (6)
C6'	0.0145 (7)	0.0186 (8)	0.0138 (7)	−0.0019 (6)	0.0034 (5)	−0.0033 (6)
C7	0.0168 (7)	0.0180 (8)	0.0152 (7)	0.0029 (6)	0.0030 (5)	0.0024 (6)
C8	0.0136 (7)	0.0145 (7)	0.0180 (7)	0.0016 (6)	0.0031 (5)	0.0009 (6)

S1—O3	1.4153 (12)	C4—C5	1.386 (2)
S1—O4	1.4191 (11)	C5—C6	1.385 (2)
S1—O1	1.5685 (11)	C5—H5	0.9500
S1—O2	1.5714 (11)	C6—H6	0.9500
O1—C3'	1.4338 (17)	C1'—C2'	1.401 (2)
O2—C7	1.4503 (18)	C1'—C6'	1.403 (2)
Cl1—C4	1.7412 (16)	C2'—C3'	1.378 (2)
Cl2—C8	1.7677 (16)	C2'—H2'	0.9500
Cl3—C8	1.7710 (15)	C3'—C4'	1.381 (2)
Cl4—C8	1.7693 (15)	C4'—C5'	1.396 (2)
C1—C2	1.398 (2)	C4'—H4'	0.9500
C1—C6	1.401 (2)	C5'—C6'	1.384 (2)
C1—C1'	1.485 (2)	C5'—H5'	0.9500
C2—C3	1.385 (2)	C6'—H6'	0.9500
C2—H2	0.9500	C7—C8	1.521 (2)
C3—C4	1.385 (2)	C7—H7A	0.9900
C3—H3	0.9500	C7—H7B	0.9900
O3—S1—O4	121.62 (8)	C6'—C1'—C1	121.85 (13)
O3—S1—O1	110.62 (6)	C3'—C2'—C1'	119.08 (14)
O4—S1—O1	105.34 (7)	C3'—C2'—H2'	120.5
O3—S1—O2	105.39 (7)	C1'—C2'—H2'	120.5
O4—S1—O2	109.79 (6)	C2'—C3'—C4'	123.88 (14)
O1—S1—O2	102.53 (6)	C2'—C3'—O1	116.77 (13)
C3'—O1—S1	119.08 (9)	C4'—C3'—O1	119.27 (14)
C7—O2—S1	118.95 (9)	C3'—C4'—C5'	116.82 (14)
C2—C1—C6	117.78 (14)	C3'—C4'—H4'	121.6
C2—C1—C1'	120.96 (13)	C5'—C4'—H4'	121.6
C6—C1—C1'	121.26 (13)	C6'—C5'—C4'	120.90 (14)
C3—C2—C1	121.53 (14)	C6'—C5'—H5'	119.6
C3—C2—H2	119.2	C4'—C5'—H5'	119.6
C1—C2—H2	119.2	C5'—C6'—C1'	121.33 (14)
C2—C3—C4	119.01 (14)	C5'—C6'—H6'	119.3
C2—C3—H3	120.5	C1'—C6'—H6'	119.3
C4—C3—H3	120.5	O2—C7—C8	107.85 (12)
C3—C4—C5	121.24 (15)	O2—C7—H7A	110.1
C3—C4—Cl1	119.25 (12)	C8—C7—H7A	110.1
C5—C4—Cl1	119.48 (12)	O2—C7—H7B	110.1
C6—C5—C4	119.01 (14)	C8—C7—H7B	110.1
C6—C5—H5	120.5	H7A—C7—H7B	108.5
C4—C5—H5	120.5	C7—C8—Cl2	110.51 (11)
C5—C6—C1	121.43 (14)	C7—C8—Cl4	110.88 (11)
C5—C6—H6	119.3	Cl2—C8—Cl4	110.07 (8)
C1—C6—H6	119.3	C7—C8—Cl3	106.40 (10)
C2'—C1'—C6'	117.97 (14)	Cl2—C8—Cl3	109.34 (8)
C2'—C1'—C1	120.18 (13)	Cl4—C8—Cl3	109.56 (8)
O3—S1—O1—C3'	−24.84 (13)	C2—C1—C1'—C6'	27.7 (2)
O4—S1—O1—C3'	−158.01 (11)	C6—C1—C1'—C6'	−152.88 (15)
O2—S1—O1—C3'	87.12 (11)	C6'—C1'—C2'—C3'	1.4 (2)
O3—S1—O2—C7	−158.44 (11)	C1—C1'—C2'—C3'	−178.90 (13)
O4—S1—O2—C7	−25.84 (13)	C1'—C2'—C3'—C4'	−0.8 (2)
O1—S1—O2—C7	85.75 (11)	C1'—C2'—C3'—O1	176.06 (13)
C6—C1—C2—C3	−0.5 (2)	S1—O1—C3'—C2'	91.88 (14)
C1'—C1—C2—C3	178.90 (14)	S1—O1—C3'—C4'	−91.13 (15)
C1—C2—C3—C4	0.2 (2)	C2'—C3'—C4'—C5'	−0.5 (2)
C2—C3—C4—C5	0.4 (2)	O1—C3'—C4'—C5'	−177.25 (13)
C2—C3—C4—Cl1	−177.88 (12)	C3'—C4'—C5'—C6'	1.2 (2)
C3—C4—C5—C6	−0.7 (2)	C4'—C5'—C6'—C1'	−0.6 (2)
Cl1—C4—C5—C6	177.54 (12)	C2'—C1'—C6'—C5'	−0.7 (2)
C4—C5—C6—C1	0.4 (2)	C1—C1'—C6'—C5'	179.55 (14)
C2—C1—C6—C5	0.2 (2)	S1—O2—C7—C8	129.66 (11)
C1'—C1—C6—C5	−179.25 (14)	O2—C7—C8—Cl2	−58.24 (14)
C2—C1—C1'—C2'	−152.01 (15)	O2—C7—C8—Cl4	64.09 (14)
C6—C1—C1'—C2'	27.4 (2)	O2—C7—C8—Cl3	−176.84 (10)