2,2',5',6-Tetra-chloro-4-[(1S)-1-methyl-prop-oxy]biphen-yl.

In the title mol-ecule, C16H14Cl4O, the dihedral angle between the least-square planes of the benzene rings is 84.40 (7)°. No unusual intermolecular interactions are present.

Related literature

For related literature about polychlorinated bi­phenyls, see: Lehmler et al. (2010 ▶); Warner et al. (2009 ▶). For crystal structures of PCB derivatives with two or less ortho chlorine substituents, see: Mannila & Rissanen (1994 ▶); Miao et al. (1996 ▶); Rissanen et al. (1988a ▶); Shaikh et al. (2008 ▶); Singh et al. (1986 ▶); van der Sluis et al. (1990 ▶); Vyas et al. (2006 ▶). For crystal structures of PCB derivatives with three ortho chlorine substituents, see: Lehmler et al. (2005 ▶); Rissanen et al. (1988b ▶). For crystal structures of PCB derivatives with four ortho chlorine substituents, see: Pedersen (1975 ▶); Singh & McKinney (1979 ▶). For literature about the Mitsunobu reaction, see: Fujita et al. (2001 ▶).

Experimental

Crystal data

C16H14Cl4O

M = 364.07

Orthorhombic,

a = 10.3301 (2) Å

b = 10.5415 (2) Å

c = 15.2160 (3) Å

V = 1656.94 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.71 mm−1

T = 90 K

0.25 × 0.25 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.843, T max = 0.946

22321 measured reflections

3797 independent reflections

3351 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.09

3797 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 1625 Friedel pairs

Flack parameter: 0.00 (6)

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014098/ng5329sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014098/ng5329Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014098/ng5329Isup3.cml

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

C16H14Cl4O	F(000) = 744
Mr = 364.07	Dx = 1.459 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2184 reflections
a = 10.3301 (2) Å	θ = 1.0–27.5°
b = 10.5415 (2) Å	µ = 0.71 mm−1
c = 15.2160 (3) Å	T = 90 K
V = 1656.94 (6) Å3	Plate, colourless
Z = 4	0.25 × 0.25 × 0.08 mm

Nonius KappaCCD diffractometer	3797 independent reflections
Radiation source: fine-focus sealed tube	3351 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 9.1 pixels mm-1	θmax = 27.5°, θmin = 2.4°
ω scans at fixed χ = 55°	h = −13→13
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −13→13
Tmin = 0.843, Tmax = 0.946	l = −19→19
22321 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.5301P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
3797 reflections	Δρmax = 0.30 e Å−3
192 parameters	Δρmin = −0.28 e Å−3
0 restraints	Absolute structure: Flack (1983), 1625 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (6)

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-value wR and goodness of fit S are based on F2. Conventional R-values 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-values based on F2 are statistically about twice as large as those based on F, and R-values based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.09110 (15)	0.46820 (16)	0.13102 (10)	0.0267 (4)
Cl1	0.32228 (5)	0.50012 (5)	0.42961 (3)	0.02188 (13)
Cl2	0.53731 (6)	0.28777 (6)	0.14184 (4)	0.02615 (14)
Cl3	0.44229 (6)	0.14044 (5)	0.36487 (4)	0.02755 (14)
Cl4	0.86539 (7)	0.55656 (7)	0.40389 (4)	0.03806 (18)
C1'	0.5425 (2)	0.3734 (2)	0.33248 (14)	0.0207 (5)
C1	0.4219 (2)	0.3999 (2)	0.28166 (14)	0.0188 (5)
C2	0.3142 (2)	0.4581 (2)	0.31899 (14)	0.0185 (4)
C3	0.2007 (2)	0.4834 (2)	0.27365 (14)	0.0206 (5)
H3	0.1296	0.5237	0.3018	0.025*
C4	0.1940 (2)	0.4478 (2)	0.18498 (15)	0.0215 (5)
C5	0.2990 (2)	0.3874 (2)	0.14558 (15)	0.0217 (5)
H5	0.2945	0.3625	0.0857	0.026*
C6	0.4089 (2)	0.3641 (2)	0.19355 (14)	0.0194 (5)
C7	−0.0337 (2)	0.5044 (2)	0.16686 (15)	0.0243 (5)
H7	−0.0453	0.4652	0.2262	0.029*
C8	−0.1328 (2)	0.4502 (2)	0.10372 (16)	0.0274 (5)
H8A	−0.1179	0.4871	0.0447	0.033*
H8B	−0.2203	0.4764	0.1232	0.033*
C9	−0.1291 (3)	0.3067 (3)	0.0965 (2)	0.0373 (7)
H9A	−0.0428	0.2797	0.0773	0.056*
H9B	−0.1938	0.2785	0.0536	0.056*
H9C	−0.1484	0.2691	0.1539	0.056*
C10	−0.0439 (3)	0.6479 (2)	0.17430 (17)	0.0325 (6)
H10A	0.0290	0.6802	0.2089	0.049*
H10B	−0.1254	0.6703	0.2034	0.049*
H10C	−0.0419	0.6855	0.1154	0.049*
C2'	0.5617 (2)	0.2565 (2)	0.37208 (15)	0.0235 (5)
C3'	0.6732 (3)	0.2293 (2)	0.41872 (16)	0.0303 (6)
H3'	0.6846	0.1480	0.4446	0.036*
C4'	0.7682 (3)	0.3210 (3)	0.42750 (17)	0.0315 (6)
H4'	0.8454	0.3033	0.4592	0.038*
C5'	0.7492 (2)	0.4387 (3)	0.38960 (15)	0.0265 (5)
C6'	0.6381 (2)	0.4661 (2)	0.34183 (15)	0.0232 (5)
H6'	0.6272	0.5472	0.3157	0.028*

	U11	U22	U33	U12	U13	U23
O1	0.0178 (8)	0.0421 (11)	0.0203 (8)	0.0042 (7)	−0.0031 (7)	−0.0005 (8)
Cl1	0.0234 (3)	0.0254 (3)	0.0169 (2)	0.0005 (2)	0.0008 (2)	−0.0006 (2)
Cl2	0.0243 (3)	0.0305 (3)	0.0237 (3)	0.0061 (2)	0.0010 (2)	−0.0041 (2)
Cl3	0.0366 (3)	0.0196 (3)	0.0264 (3)	−0.0011 (2)	−0.0004 (3)	0.0009 (2)
Cl4	0.0238 (3)	0.0563 (4)	0.0341 (3)	−0.0085 (3)	−0.0017 (3)	−0.0120 (3)
C1'	0.0194 (12)	0.0243 (11)	0.0182 (10)	0.0029 (10)	0.0008 (9)	−0.0018 (9)
C1	0.0194 (12)	0.0159 (10)	0.0212 (11)	0.0010 (9)	−0.0003 (9)	0.0032 (8)
C2	0.0201 (12)	0.0185 (10)	0.0168 (10)	−0.0016 (9)	0.0004 (9)	0.0018 (9)
C3	0.0198 (12)	0.0215 (12)	0.0205 (10)	0.0017 (9)	0.0020 (9)	−0.0004 (9)
C4	0.0194 (12)	0.0240 (11)	0.0209 (11)	−0.0024 (10)	−0.0016 (9)	0.0032 (10)
C5	0.0230 (12)	0.0238 (11)	0.0182 (11)	−0.0001 (9)	−0.0013 (10)	−0.0013 (9)
C6	0.0174 (11)	0.0185 (11)	0.0223 (11)	−0.0011 (9)	0.0040 (9)	0.0004 (9)
C7	0.0178 (12)	0.0292 (11)	0.0258 (11)	0.0039 (10)	−0.0020 (9)	−0.0002 (10)
C8	0.0209 (12)	0.0294 (13)	0.0319 (12)	0.0032 (11)	−0.0061 (11)	−0.0004 (11)
C9	0.0304 (14)	0.0307 (14)	0.0507 (17)	0.0060 (12)	−0.0084 (14)	−0.0089 (13)
C10	0.0313 (14)	0.0272 (13)	0.0388 (14)	0.0007 (12)	−0.0068 (12)	−0.0012 (11)
C2'	0.0278 (13)	0.0237 (11)	0.0189 (11)	0.0045 (10)	−0.0021 (10)	−0.0035 (9)
C3'	0.0382 (15)	0.0269 (13)	0.0258 (12)	0.0154 (11)	−0.0072 (11)	−0.0039 (10)
C4'	0.0281 (14)	0.0423 (16)	0.0243 (12)	0.0143 (12)	−0.0086 (11)	−0.0104 (11)
C5'	0.0168 (12)	0.0398 (14)	0.0228 (12)	−0.0010 (11)	−0.0001 (10)	−0.0090 (11)
C6'	0.0213 (12)	0.0274 (12)	0.0210 (11)	0.0013 (10)	0.0000 (9)	−0.0008 (9)

O1—C4	1.360 (3)	C7—C10	1.520 (3)
O1—C7	1.451 (3)	C7—H7	1.0000
Cl1—C2	1.743 (2)	C8—C9	1.518 (4)
Cl2—C6	1.739 (2)	C8—H8A	0.9900
Cl3—C2'	1.740 (3)	C8—H8B	0.9900
Cl4—C5'	1.741 (3)	C9—H9A	0.9800
C1'—C2'	1.386 (3)	C9—H9B	0.9800
C1'—C6'	1.396 (3)	C9—H9C	0.9800
C1'—C1	1.493 (3)	C10—H10A	0.9800
C1—C2	1.391 (3)	C10—H10B	0.9800
C1—C6	1.399 (3)	C10—H10C	0.9800
C2—C3	1.386 (3)	C2'—C3'	1.383 (3)
C3—C4	1.402 (3)	C3'—C4'	1.384 (4)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.393 (3)	C4'—C5'	1.382 (4)
C5—C6	1.372 (3)	C4'—H4'	0.9500
C5—H5	0.9500	C5'—C6'	1.389 (3)
C7—C8	1.515 (3)	C6'—H6'	0.9500
C4—O1—C7	120.62 (17)	C7—C8—H8B	108.8
C2'—C1'—C6'	118.5 (2)	C9—C8—H8B	108.8
C2'—C1'—C1	120.7 (2)	H8A—C8—H8B	107.7
C6'—C1'—C1	120.8 (2)	C8—C9—H9A	109.5
C2—C1—C6	115.7 (2)	C8—C9—H9B	109.5
C2—C1—C1'	122.57 (19)	H9A—C9—H9B	109.5
C6—C1—C1'	121.7 (2)	C8—C9—H9C	109.5
C3—C2—C1	123.9 (2)	H9A—C9—H9C	109.5
C3—C2—Cl1	118.18 (17)	H9B—C9—H9C	109.5
C1—C2—Cl1	117.91 (17)	C7—C10—H10A	109.5
C2—C3—C4	118.0 (2)	C7—C10—H10B	109.5
C2—C3—H3	121.0	H10A—C10—H10B	109.5
C4—C3—H3	121.0	C7—C10—H10C	109.5
O1—C4—C5	114.89 (19)	H10A—C10—H10C	109.5
O1—C4—C3	125.2 (2)	H10B—C10—H10C	109.5
C5—C4—C3	119.9 (2)	C3'—C2'—C1'	121.8 (2)
C6—C5—C4	119.8 (2)	C3'—C2'—Cl3	118.48 (18)
C6—C5—H5	120.1	C1'—C2'—Cl3	119.76 (18)
C4—C5—H5	120.1	C2'—C3'—C4'	119.7 (2)
C5—C6—C1	122.7 (2)	C2'—C3'—H3'	120.2
C5—C6—Cl2	118.25 (17)	C4'—C3'—H3'	120.2
C1—C6—Cl2	119.03 (18)	C5'—C4'—C3'	119.1 (2)
O1—C7—C8	105.22 (18)	C5'—C4'—H4'	120.4
O1—C7—C10	110.6 (2)	C3'—C4'—H4'	120.4
C8—C7—C10	112.1 (2)	C4'—C5'—C6'	121.5 (2)
O1—C7—H7	109.6	C4'—C5'—Cl4	119.38 (19)
C8—C7—H7	109.6	C6'—C5'—Cl4	119.1 (2)
C10—C7—H7	109.6	C5'—C6'—C1'	119.5 (2)
C7—C8—C9	113.9 (2)	C5'—C6'—H6'	120.3
C7—C8—H8A	108.8	C1'—C6'—H6'	120.3
C9—C8—H8A	108.8
C2'—C1'—C1—C2	94.3 (3)	C2—C1—C6—Cl2	−178.73 (16)
C6'—C1'—C1—C2	−85.2 (3)	C1'—C1—C6—Cl2	−0.5 (3)
C2'—C1'—C1—C6	−83.9 (3)	C4—O1—C7—C8	−149.7 (2)
C6'—C1'—C1—C6	96.7 (3)	C4—O1—C7—C10	89.1 (3)
C6—C1—C2—C3	−1.5 (3)	O1—C7—C8—C9	61.7 (3)
C1'—C1—C2—C3	−179.7 (2)	C10—C7—C8—C9	−178.1 (2)
C6—C1—C2—Cl1	177.90 (17)	C6'—C1'—C2'—C3'	−1.2 (3)
C1'—C1—C2—Cl1	−0.4 (3)	C1—C1'—C2'—C3'	179.3 (2)
C1—C2—C3—C4	0.2 (3)	C6'—C1'—C2'—Cl3	177.88 (16)
Cl1—C2—C3—C4	−179.12 (18)	C1—C1'—C2'—Cl3	−1.6 (3)
C7—O1—C4—C5	166.6 (2)	C1'—C2'—C3'—C4'	0.9 (4)
C7—O1—C4—C3	−14.0 (3)	Cl3—C2'—C3'—C4'	−178.25 (19)
C2—C3—C4—O1	−178.5 (2)	C2'—C3'—C4'—C5'	0.3 (4)
C2—C3—C4—C5	0.8 (3)	C3'—C4'—C5'—C6'	−1.0 (4)
O1—C4—C5—C6	178.9 (2)	C3'—C4'—C5'—Cl4	177.56 (19)
C3—C4—C5—C6	−0.6 (3)	C4'—C5'—C6'—C1'	0.7 (3)
C4—C5—C6—C1	−0.8 (3)	Cl4—C5'—C6'—C1'	−177.93 (17)
C4—C5—C6—Cl2	179.69 (18)	C2'—C1'—C6'—C5'	0.4 (3)
C2—C1—C6—C5	1.7 (3)	C1—C1'—C6'—C5'	179.9 (2)
C1'—C1—C6—C5	−180.0 (2)