5,5'-Dichloro-2,2'-dimeth-oxy-biphen-yl.

In the title mol-ecule, C14H12Cl2O2, the dihedral angle between the least-square planes of the benzene rings is 62.17 (6)°. Both meth-oxy groups are slightly out of the plane of the benzene rings to which they are attached, making dihedral angles of 4.22 (18) and 18.82 (16)°.

Related literature

For background to polychlorinated biphenyls, see: Basu et al. (2009 ▶); Hu et al. (2008 ▶); Kaminsky et al. (1981 ▶); Kennedy et al. (1981 ▶); McLean et al. (1996 ▶); Rodenburg et al. (2010 ▶). For related structures, see: Chattopadhyay et al. (1987 ▶); Nakaema et al. (2008 ▶); Sun et al. (2001 ▶). For the synthesis of the title compound, see: Joshi et al. (2011 ▶).

Experimental

Crystal data

C14H12Cl2O2

M = 283.14

Monoclinic,

a = 10.9629 (2) Å

b = 7.2177 (1) Å

c = 16.7812 (3) Å

β = 104.7108 (7)°

V = 1284.32 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 90 K

0.22 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.899, T max = 0.916

21357 measured reflections

2948 independent reflections

2347 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.111

S = 1.11

2948 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.41 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681300826X/lh5598sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300826X/lh5598Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300826X/lh5598Isup3.cml

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

C14H12Cl2O2	F(000) = 584
Mr = 283.14	Dx = 1.464 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3160 reflections
a = 10.9629 (2) Å	θ = 1.0–27.5°
b = 7.2177 (1) Å	µ = 0.50 mm−1
c = 16.7812 (3) Å	T = 90 K
β = 104.7108 (7)°	Block, colourless
V = 1284.32 (4) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Nonius KappaCCD diffractometer	2948 independent reflections
Radiation source: fine-focus sealed tube	2347 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 9.1 pixels mm-1	θmax = 27.5°, θmin = 2.0°
ω scans at fixed χ = 55°	h = −14→14
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −9→9
Tmin = 0.899, Tmax = 0.916	l = −21→21
21357 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.9091P] where P = (Fo2 + 2Fc2)/3
2948 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.41 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-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
Cl1	0.07535 (4)	0.15602 (7)	0.32405 (3)	0.02285 (15)
O1	0.56298 (12)	0.53852 (19)	0.38856 (9)	0.0168 (3)
C1	0.43664 (17)	0.2807 (3)	0.33719 (12)	0.0137 (4)
C2	0.45037 (18)	0.4500 (3)	0.37970 (12)	0.0149 (4)
C3	0.35230 (18)	0.5203 (3)	0.40971 (12)	0.0170 (4)
H3	0.3636	0.6321	0.4406	0.020*
C4	0.23774 (18)	0.4264 (3)	0.39443 (12)	0.0171 (4)
H4	0.1709	0.4726	0.4154	0.020*
C5	0.22250 (18)	0.2655 (3)	0.34850 (12)	0.0170 (4)
C6	0.32045 (18)	0.1903 (3)	0.32061 (12)	0.0163 (4)
H6	0.3085	0.0776	0.2903	0.020*
C7	0.56729 (19)	0.7317 (3)	0.40866 (14)	0.0211 (4)
H7A	0.4958	0.7952	0.3718	0.032*
H7B	0.6463	0.7851	0.4020	0.032*
H7C	0.5628	0.7470	0.4659	0.032*
Cl1'	0.59609 (5)	0.10229 (8)	0.08207 (3)	0.02197 (15)
O1'	0.66596 (13)	0.1598 (2)	0.44014 (8)	0.0174 (3)
C1'	0.54159 (18)	0.2061 (3)	0.30496 (12)	0.0137 (4)
C2'	0.65747 (18)	0.1509 (3)	0.35747 (12)	0.0147 (4)
C3'	0.75356 (18)	0.0855 (3)	0.32448 (12)	0.0163 (4)
H3'	0.8319	0.0501	0.3603	0.020*
C4'	0.73626 (19)	0.0711 (3)	0.23964 (13)	0.0175 (4)
H4'	0.8024	0.0277	0.2173	0.021*
C5'	0.62136 (18)	0.1210 (3)	0.18870 (12)	0.0157 (4)
C6'	0.52457 (18)	0.1888 (3)	0.22031 (12)	0.0156 (4)
H6'	0.4465	0.2235	0.1839	0.019*
C7'	0.78413 (19)	0.1104 (3)	0.49485 (13)	0.0212 (5)
H7'1	0.8051	−0.0177	0.4841	0.032*
H7'2	0.7782	0.1214	0.5520	0.032*
H7'3	0.8501	0.1935	0.4860	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.0134 (2)	0.0267 (3)	0.0286 (3)	−0.00368 (19)	0.0056 (2)	0.0006 (2)
O1	0.0159 (7)	0.0120 (7)	0.0239 (8)	−0.0027 (5)	0.0075 (6)	−0.0041 (6)
C1	0.0140 (9)	0.0144 (9)	0.0130 (9)	0.0016 (7)	0.0040 (7)	0.0015 (8)
C2	0.0135 (9)	0.0158 (10)	0.0151 (9)	0.0010 (8)	0.0032 (7)	0.0029 (8)
C3	0.0188 (10)	0.0146 (10)	0.0178 (10)	0.0016 (8)	0.0048 (8)	−0.0016 (8)
C4	0.0146 (9)	0.0195 (10)	0.0186 (10)	0.0038 (8)	0.0070 (8)	0.0012 (8)
C5	0.0127 (9)	0.0195 (10)	0.0184 (10)	−0.0010 (8)	0.0031 (7)	0.0035 (8)
C6	0.0172 (10)	0.0152 (10)	0.0167 (10)	0.0009 (8)	0.0048 (8)	−0.0001 (8)
C7	0.0218 (10)	0.0122 (10)	0.0293 (12)	−0.0031 (8)	0.0065 (9)	−0.0035 (9)
Cl1'	0.0204 (3)	0.0295 (3)	0.0170 (3)	−0.0005 (2)	0.00670 (19)	−0.0048 (2)
O1'	0.0169 (7)	0.0198 (7)	0.0153 (7)	0.0038 (6)	0.0036 (5)	0.0010 (6)
C1'	0.0153 (9)	0.0084 (9)	0.0189 (10)	−0.0007 (7)	0.0069 (7)	−0.0015 (8)
C2'	0.0165 (9)	0.0113 (9)	0.0172 (10)	−0.0017 (7)	0.0058 (8)	−0.0009 (8)
C3'	0.0135 (9)	0.0140 (9)	0.0215 (10)	0.0008 (8)	0.0046 (8)	−0.0002 (8)
C4'	0.0169 (9)	0.0135 (10)	0.0250 (11)	0.0007 (8)	0.0109 (8)	−0.0015 (8)
C5'	0.0197 (10)	0.0146 (10)	0.0142 (9)	−0.0031 (8)	0.0069 (8)	−0.0020 (8)
C6'	0.0142 (9)	0.0127 (9)	0.0201 (10)	−0.0004 (7)	0.0047 (8)	0.0000 (8)
C7'	0.0202 (10)	0.0224 (11)	0.0177 (10)	0.0052 (9)	−0.0016 (8)	0.0004 (9)

Cl1—C5	1.749 (2)	Cl1'—C5'	1.745 (2)
O1—C2	1.364 (2)	O1'—C2'	1.368 (2)
O1—C7	1.432 (2)	O1'—C7'	1.430 (2)
C1—C6	1.395 (3)	C1'—C6'	1.391 (3)
C1—C2	1.404 (3)	C1'—C2'	1.407 (3)
C1—C1'	1.491 (2)	C2'—C3'	1.391 (3)
C2—C3	1.393 (3)	C3'—C4'	1.392 (3)
C3—C4	1.392 (3)	C3'—H3'	0.9500
C3—H3	0.9500	C4'—C5'	1.379 (3)
C4—C5	1.381 (3)	C4'—H4'	0.9500
C4—H4	0.9500	C5'—C6'	1.390 (3)
C5—C6	1.386 (3)	C6'—H6'	0.9500
C6—H6	0.9500	C7'—H7'1	0.9800
C7—H7A	0.9800	C7'—H7'2	0.9800
C7—H7B	0.9800	C7'—H7'3	0.9800
C7—H7C	0.9800
C2—O1—C7	117.14 (15)	C2'—O1'—C7'	117.18 (15)
C6—C1—C2	118.90 (17)	C6'—C1'—C2'	118.68 (17)
C6—C1—C1'	120.57 (17)	C6'—C1'—C1	119.16 (17)
C2—C1—C1'	120.38 (16)	C2'—C1'—C1	122.16 (17)
O1—C2—C3	123.39 (18)	O1'—C2'—C3'	123.77 (18)
O1—C2—C1	116.12 (16)	O1'—C2'—C1'	116.10 (16)
C3—C2—C1	120.48 (17)	C3'—C2'—C1'	120.09 (18)
C4—C3—C2	119.96 (19)	C2'—C3'—C4'	120.81 (18)
C4—C3—H3	120.0	C2'—C3'—H3'	119.6
C2—C3—H3	120.0	C4'—C3'—H3'	119.6
C5—C4—C3	119.19 (18)	C5'—C4'—C3'	118.72 (18)
C5—C4—H4	120.4	C5'—C4'—H4'	120.6
C3—C4—H4	120.4	C3'—C4'—H4'	120.6
C4—C5—C6	121.58 (18)	C4'—C5'—C6'	121.41 (18)
C4—C5—Cl1	119.00 (15)	C4'—C5'—Cl1'	119.85 (15)
C6—C5—Cl1	119.41 (16)	C6'—C5'—Cl1'	118.74 (15)
C5—C6—C1	119.72 (18)	C5'—C6'—C1'	120.26 (18)
C5—C6—H6	120.1	C5'—C6'—H6'	119.9
C1—C6—H6	120.1	C1'—C6'—H6'	119.9
O1—C7—H7A	109.5	O1'—C7'—H7'1	109.5
O1—C7—H7B	109.5	O1'—C7'—H7'2	109.5
H7A—C7—H7B	109.5	H7'1—C7'—H7'2	109.5
O1—C7—H7C	109.5	O1'—C7'—H7'3	109.5
H7A—C7—H7C	109.5	H7'1—C7'—H7'3	109.5
H7B—C7—H7C	109.5	H7'2—C7'—H7'3	109.5
C7—O1—C2—C3	−17.7 (3)	C6—C1—C1'—C2'	−119.2 (2)
C7—O1—C2—C1	161.82 (17)	C2—C1—C1'—C2'	65.4 (3)
C6—C1—C2—O1	−175.20 (17)	C7'—O1'—C2'—C3'	4.5 (3)
C1'—C1—C2—O1	0.3 (3)	C7'—O1'—C2'—C1'	−177.96 (17)
C6—C1—C2—C3	4.3 (3)	C6'—C1'—C2'—O1'	−175.93 (17)
C1'—C1—C2—C3	179.85 (18)	C1—C1'—C2'—O1'	3.6 (3)
O1—C2—C3—C4	176.63 (18)	C6'—C1'—C2'—C3'	1.7 (3)
C1—C2—C3—C4	−2.9 (3)	C1—C1'—C2'—C3'	−178.75 (18)
C2—C3—C4—C5	−0.9 (3)	O1'—C2'—C3'—C4'	176.60 (18)
C3—C4—C5—C6	3.2 (3)	C1'—C2'—C3'—C4'	−0.9 (3)
C3—C4—C5—Cl1	−176.05 (15)	C2'—C3'—C4'—C5'	−0.7 (3)
C4—C5—C6—C1	−1.7 (3)	C3'—C4'—C5'—C6'	1.5 (3)
Cl1—C5—C6—C1	177.55 (15)	C3'—C4'—C5'—Cl1'	−179.32 (15)
C2—C1—C6—C5	−2.1 (3)	C4'—C5'—C6'—C1'	−0.6 (3)
C1'—C1—C6—C5	−177.59 (18)	Cl1'—C5'—C6'—C1'	−179.82 (15)
C6—C1—C1'—C6'	60.3 (3)	C2'—C1'—C6'—C5'	−1.0 (3)
C2—C1—C1'—C6'	−115.1 (2)	C1—C1'—C6'—C5'	179.49 (17)