4,4'-Diiodo-3,3'-dimethoxy-biphen-yl.

The mol-ecules of the title compound, C(14)H(12)I(2)O(2), lie on inversion centers and are linked by I⋯O inter-actions with inter-molecular distances of 3.324 (3) Å. The aromatic rings display no significant inter-calation or stacking inter-actions.

Related literature

For related literature see: Sakai & Matile (2003 ▶); Sakai et al. (1997 ▶); Anelli et al. (2001 ▶); Baumeister et al. (2001 ▶); Fidzinski et al. (2003 ▶); Mullen & Wegner (1998 ▶); Schwab & Levin (1999 ▶); Sisson et al. (2006 ▶).

Experimental

Crystal data

C14H12I2O2

M = 466.04

Monoclinic,

a = 6.8616 (14) Å

b = 7.7386 (15) Å

c = 13.435 (3) Å

β = 102.43 (3)°

V = 696.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 4.50 mm−1

T = 153 (2) K

0.36 × 0.26 × 0.24 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.241, T max = 0.337

5295 measured reflections

1417 independent reflections

1381 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.062

S = 1.13

1417 reflections

84 parameters

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.90 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: REQAB (Jacobson, 1998 ▶) and CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801129X/pv2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801129X/pv2077Isup2.hkl

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

C14H12I2O2	F(000) = 436
Mr = 466.04	Dx = 2.222 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2340 reflections
a = 6.8616 (14) Å	θ = 3.0–26.4°
b = 7.7386 (15) Å	µ = 4.51 mm−1
c = 13.435 (3) Å	T = 153 K
β = 102.43 (3)°	Chip, colorless
V = 696.7 (2) Å3	0.36 × 0.26 × 0.24 mm
Z = 2

Rigaku Mercury CCD diffractometer	1417 independent reflections
Radiation source: Sealed Tube	1381 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.039
Detector resolution: 14.6306 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −9→9
Tmin = 0.241, Tmax = 0.337	l = −16→11
5295 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)] = 0.024	H-atom parameters constrained
wR(F2) = 0.062	w = 1/[σ2(Fo2) + (0.0318P)2 + 1.081P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
1417 reflections	Δρmax = 1.08 e Å−3
84 parameters	Δρmin = −0.90 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0437 (19)

Experimental. 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 > 2sigma(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.

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.

	x	y	z	Uiso*/Ueq
I1	0.28040 (3)	0.14667 (2)	0.340534 (14)	0.01974 (14)
O1	0.5702 (3)	0.3479 (3)	0.22987 (17)	0.0195 (5)
C1	0.5402 (4)	0.2888 (3)	0.3985 (2)	0.0152 (5)
C2	0.6482 (4)	0.3641 (3)	0.3325 (2)	0.0129 (6)
C3	0.8273 (4)	0.4479 (4)	0.3731 (2)	0.0151 (5)
H3	0.9008	0.5005	0.3278	0.018*
C4	0.9026 (4)	0.4569 (3)	0.4787 (2)	0.0139 (5)
C5	0.7896 (4)	0.3821 (4)	0.5427 (2)	0.0183 (6)
H5	0.8366	0.3884	0.6153	0.022*
C6	0.6107 (4)	0.2990 (4)	0.5026 (2)	0.0203 (6)
H6	0.5353	0.2483	0.5475	0.024*
C7	0.6900 (5)	0.4047 (5)	0.1613 (2)	0.0230 (7)
H7A	0.7072	0.5277	0.1668	0.035*
H7B	0.6251	0.3752	0.0927	0.035*
H7C	0.8180	0.3493	0.1783	0.035*

	U11	U22	U33	U12	U13	U23
I1	0.01475 (17)	0.02317 (18)	0.02110 (17)	−0.00579 (6)	0.00339 (9)	−0.00124 (6)
O1	0.0194 (10)	0.0253 (12)	0.0136 (10)	−0.0088 (8)	0.0029 (8)	−0.0017 (7)
C1	0.0090 (11)	0.0127 (12)	0.0230 (13)	−0.0005 (10)	0.0019 (10)	−0.0010 (10)
C2	0.0140 (13)	0.0108 (13)	0.0137 (14)	0.0005 (9)	0.0024 (10)	−0.0009 (9)
C3	0.0156 (12)	0.0141 (12)	0.0161 (13)	−0.0002 (10)	0.0042 (10)	0.0009 (10)
C4	0.0119 (12)	0.0111 (11)	0.0180 (13)	0.0021 (10)	0.0019 (10)	0.0018 (10)
C5	0.0143 (13)	0.0267 (14)	0.0121 (13)	−0.0008 (12)	−0.0014 (10)	0.0032 (11)
C6	0.0148 (13)	0.0258 (15)	0.0200 (14)	0.0004 (12)	0.0028 (10)	0.0021 (12)
C7	0.0239 (14)	0.0306 (17)	0.0145 (14)	−0.0100 (14)	0.0038 (11)	−0.0008 (12)

I1—C1	2.097 (3)	C4—C5	1.401 (4)
O1—C2	1.373 (4)	C4—C4i	1.493 (5)
O1—C7	1.429 (4)	C5—C6	1.388 (4)
C1—C6	1.380 (4)	C5—H5	0.9600
C1—C2	1.399 (4)	C6—H6	0.9600
C2—C3	1.392 (4)	C7—H7A	0.9599
C3—C4	1.404 (4)	C7—H7B	0.9599
C3—H3	0.9600	C7—H7C	0.9599
C2—O1—C7	117.8 (2)	C6—C5—C4	120.8 (3)
C6—C1—C2	120.0 (3)	C6—C5—H5	119.6
C6—C1—I1	119.4 (2)	C4—C5—H5	119.6
C2—C1—I1	120.5 (2)	C1—C6—C5	120.5 (3)
O1—C2—C3	123.8 (3)	C1—C6—H6	119.7
O1—C2—C1	117.0 (2)	C5—C6—H6	119.7
C3—C2—C1	119.3 (3)	O1—C7—H7A	109.5
C2—C3—C4	121.4 (3)	O1—C7—H7B	109.5
C2—C3—H3	119.3	H7A—C7—H7B	109.5
C4—C3—H3	119.3	O1—C7—H7C	109.5
C5—C4—C3	117.9 (2)	H7A—C7—H7C	109.5
C5—C4—C4i	121.2 (3)	H7B—C7—H7C	109.5
C3—C4—C4i	120.9 (3)