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

Mol-ecules of the title compound, C(14)H(13)IO(2), exhibit no π-π inter-actions. The dihedral angle between the two aromatic rings is 43.72 (9)°. The shortest inter-molecular I⋯O distance is 3.408 (2) Å, which is significantly less than the sum of the van der Waals radii for I and O (3.50 Å).

Related literature

For related literature, see: Litvinchuk et al. (2004 ▶); Baudry et al. (2006 ▶); Sisson et al. (2006 ▶); Ali et al. (2008 ▶); Ibad et al. (2008 ▶); Baumeister et al. (2001 ▶).

Experimental

Crystal data

C14H13IO2

M = 340.14

Monoclinic,

a = 11.932 (2) Å

b = 15.382 (3) Å

c = 6.9940 (14) Å

β = 90.68 (3)°

V = 1283.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.48 mm−1

T = 153 (2) K

0.43 × 0.38 × 0.36 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.415, T max = 0.469 (expected range = 0.362–0.409)

9179 measured reflections

2337 independent reflections

2206 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.053

S = 1.09

2337 reflections

156 parameters

H-atom parameters constrained

Δρmax = 1.19 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2006 ▶); cell refinement: CrystalClear; data reduction: 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/S1600536808019557/bt2736sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019557/bt2736Isup2.hkl

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

C14H13IO2	F000 = 664
Mr = 340.14	Dx = 1.760 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 11.932 (2) Å	Cell parameters from 4368 reflections
b = 15.382 (3) Å	θ = 2.9–26.4º
c = 6.9940 (14) Å	µ = 2.48 mm−1
β = 90.68 (3)º	T = 153 (2) K
V = 1283.6 (4) Å3	Chip, colorless
Z = 4	0.43 × 0.38 × 0.36 mm

Rigaku Mercury CCD diffractometer	2337 independent reflections
Radiation source: Sealed Tube	2206 reflections with I > 2σ(I)
Monochromator: Graphite Monochromator	Rint = 0.021
Detector resolution: 14.6306 pixels mm-1	θmax = 25.4º
T = 153(2) K	θmin = 3.2º
ω scans	h = −14→14
Absorption correction: multi-scan(Jacobson, 1998)	k = −18→18
Tmin = 0.415, Tmax = 0.469	l = −8→6
9179 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)] = 0.022	H-atom parameters constrained
wR(F2) = 0.054	w = 1/[σ2(Fo2) + (0.0234P)2 + 1.6489P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2337 reflections	Δρmax = 1.19 e Å−3
156 parameters	Δρmin = −0.45 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > σ(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
I1	0.351251 (14)	0.680339 (10)	0.13178 (2)	0.02636 (8)
C1	0.3045 (2)	0.59482 (15)	0.3506 (3)	0.0207 (5)
C2	0.37606 (19)	0.58357 (15)	0.5087 (3)	0.0187 (5)
C3	0.34448 (17)	0.52906 (15)	0.6519 (3)	0.0158 (4)
H3A	0.3926	0.5222	0.7618	0.019*
C4	0.2424 (2)	0.48233 (15)	0.6425 (3)	0.0203 (5)
C5	0.1732 (2)	0.49371 (17)	0.4818 (4)	0.0251 (5)
H5A	0.1037	0.4625	0.4718	0.030*
C6	0.2044 (2)	0.55002 (17)	0.3361 (4)	0.0250 (5)
H6A	0.1566	0.5577	0.2261	0.030*
C7	0.2107 (2)	0.42139 (15)	0.7984 (3)	0.0203 (5)
C8	0.2903 (2)	0.36430 (16)	0.8774 (3)	0.0219 (5)
H8A	0.3663	0.3652	0.8341	0.026*
C9	0.2583 (2)	0.30671 (16)	1.0183 (4)	0.0233 (5)
H9A	0.3129	0.2672	1.0707	0.028*
C10	0.1492 (2)	0.30429 (16)	1.0864 (4)	0.0235 (5)
H10A	0.1285	0.2638	1.1844	0.028*
C11	0.0710 (2)	0.36164 (16)	1.0095 (4)	0.0226 (5)
C12	0.1018 (2)	0.41935 (16)	0.8648 (4)	0.0222 (5)
H12A	0.0468	0.4580	0.8107	0.027*
C13	0.5475 (2)	0.62115 (17)	0.6703 (4)	0.0259 (5)
H13A	0.6153	0.6529	0.6478	0.039*
H13B	0.5651	0.5611	0.6924	0.039*
H13C	0.5108	0.6446	0.7803	0.039*
C14	−0.0733 (3)	0.31310 (18)	1.2189 (4)	0.0340 (7)
H14A	−0.1489	0.3273	1.2525	0.051*
H14B	−0.0248	0.3222	1.3275	0.051*
H14C	−0.0696	0.2533	1.1802	0.051*
O1	0.47461 (14)	0.62845 (11)	0.5063 (2)	0.0238 (4)
O2	−0.03855 (15)	0.36749 (13)	1.0649 (3)	0.0334 (4)

	U11	U22	U33	U12	U13	U23
I1	0.02789 (11)	0.02800 (11)	0.02336 (11)	0.00115 (6)	0.00705 (7)	0.00536 (6)
C1	0.0225 (12)	0.0197 (11)	0.0200 (12)	−0.0003 (9)	0.0043 (9)	0.0001 (9)
C2	0.0185 (11)	0.0174 (11)	0.0205 (11)	−0.0006 (9)	0.0036 (9)	−0.0022 (9)
C3	0.0133 (10)	0.0184 (11)	0.0156 (11)	0.0032 (8)	−0.0027 (8)	−0.0051 (8)
C4	0.0206 (11)	0.0204 (11)	0.0200 (12)	−0.0002 (9)	0.0016 (9)	−0.0006 (9)
C5	0.0201 (12)	0.0284 (13)	0.0267 (13)	−0.0055 (10)	−0.0031 (10)	0.0035 (10)
C6	0.0220 (12)	0.0302 (13)	0.0226 (12)	−0.0008 (10)	−0.0047 (10)	0.0019 (10)
C7	0.0224 (11)	0.0176 (11)	0.0209 (12)	−0.0035 (9)	−0.0037 (9)	−0.0022 (9)
C8	0.0206 (12)	0.0229 (12)	0.0222 (12)	−0.0008 (9)	−0.0026 (9)	−0.0011 (10)
C9	0.0248 (13)	0.0243 (12)	0.0208 (12)	0.0030 (10)	−0.0053 (10)	−0.0015 (10)
C10	0.0290 (13)	0.0228 (12)	0.0188 (12)	−0.0031 (10)	−0.0017 (10)	0.0026 (10)
C11	0.0213 (12)	0.0226 (12)	0.0239 (12)	−0.0018 (9)	0.0008 (10)	0.0013 (10)
C12	0.0211 (12)	0.0197 (11)	0.0259 (13)	0.0017 (9)	−0.0010 (9)	0.0030 (10)
C13	0.0215 (12)	0.0306 (13)	0.0257 (13)	−0.0047 (10)	0.0006 (10)	−0.0071 (11)
C14	0.0318 (15)	0.0372 (16)	0.0331 (16)	−0.0057 (11)	0.0109 (12)	0.0092 (12)
O1	0.0195 (8)	0.0284 (9)	0.0236 (9)	−0.0066 (7)	0.0013 (7)	−0.0004 (7)
O2	0.0239 (9)	0.0370 (11)	0.0396 (11)	0.0024 (8)	0.0080 (8)	0.0157 (9)

I1—C1	2.098 (2)	C9—C10	1.393 (4)
C1—C6	1.382 (3)	C9—H9A	0.9600
C1—C2	1.400 (3)	C10—C11	1.388 (4)
C2—C3	1.363 (3)	C10—H10A	0.9600
C2—O1	1.364 (3)	C11—O2	1.370 (3)
C3—C4	1.416 (3)	C11—C12	1.399 (3)
C3—H3A	0.9600	C12—H12A	0.9600
C4—C5	1.397 (3)	C13—O1	1.436 (3)
C4—C7	1.490 (3)	C13—H13A	0.9599
C5—C6	1.391 (4)	C13—H13B	0.9599
C5—H5A	0.9600	C13—H13C	0.9599
C6—H6A	0.9600	C14—O2	1.429 (3)
C7—C12	1.386 (3)	C14—H14A	0.9599
C7—C8	1.402 (3)	C14—H14B	0.9599
C8—C9	1.382 (4)	C14—H14C	0.9599
C8—H8A	0.9600
I1···O1i	3.408 (2)
C6—C1—C2	121.0 (2)	C8—C9—H9A	119.1
C6—C1—I1	119.76 (18)	C10—C9—H9A	119.1
C2—C1—I1	119.25 (17)	C11—C10—C9	118.5 (2)
C3—C2—O1	124.5 (2)	C11—C10—H10A	120.7
C3—C2—C1	119.0 (2)	C9—C10—H10A	120.7
O1—C2—C1	116.5 (2)	O2—C11—C10	124.8 (2)
C2—C3—C4	121.6 (2)	O2—C11—C12	115.0 (2)
C2—C3—H3A	119.2	C10—C11—C12	120.1 (2)
C4—C3—H3A	119.2	C7—C12—C11	120.8 (2)
C5—C4—C3	118.3 (2)	C7—C12—H12A	119.6
C5—C4—C7	121.0 (2)	C11—C12—H12A	119.6
C3—C4—C7	120.7 (2)	O1—C13—H13A	109.5
C6—C5—C4	120.4 (2)	O1—C13—H13B	109.5
C6—C5—H5A	119.8	H13A—C13—H13B	109.5
C4—C5—H5A	119.8	O1—C13—H13C	109.5
C1—C6—C5	119.7 (2)	H13A—C13—H13C	109.5
C1—C6—H6A	120.1	H13B—C13—H13C	109.5
C5—C6—H6A	120.1	O2—C14—H14A	109.5
C12—C7—C8	119.1 (2)	O2—C14—H14B	109.5
C12—C7—C4	120.4 (2)	H14A—C14—H14B	109.5
C8—C7—C4	120.4 (2)	O2—C14—H14C	109.5
C9—C8—C7	119.4 (2)	H14A—C14—H14C	109.5
C9—C8—H8A	120.3	H14B—C14—H14C	109.5
C7—C8—H8A	120.3	C2—O1—C13	117.71 (19)
C8—C9—C10	121.9 (2)	C11—O2—C14	117.4 (2)
C6—C1—C2—C3	−1.6 (4)	C3—C4—C7—C8	−43.5 (3)
I1—C1—C2—C3	178.93 (16)	C12—C7—C8—C9	0.6 (4)
C6—C1—C2—O1	177.8 (2)	C4—C7—C8—C9	−178.3 (2)
I1—C1—C2—O1	−1.7 (3)	C7—C8—C9—C10	−0.8 (4)
O1—C2—C3—C4	−178.0 (2)	C8—C9—C10—C11	0.0 (4)
C1—C2—C3—C4	1.3 (3)	C9—C10—C11—O2	−178.8 (2)
C2—C3—C4—C5	−0.4 (3)	C9—C10—C11—C12	1.0 (4)
C2—C3—C4—C7	178.5 (2)	C8—C7—C12—C11	0.4 (4)
C3—C4—C5—C6	−0.4 (4)	C4—C7—C12—C11	179.2 (2)
C7—C4—C5—C6	−179.2 (2)	O2—C11—C12—C7	178.7 (2)
C2—C1—C6—C5	0.9 (4)	C10—C11—C12—C7	−1.2 (4)
I1—C1—C6—C5	−179.64 (19)	C3—C2—O1—C13	−3.3 (3)
C4—C5—C6—C1	0.1 (4)	C1—C2—O1—C13	177.3 (2)
C5—C4—C7—C12	−43.6 (3)	C10—C11—O2—C14	2.9 (4)
C3—C4—C7—C12	137.6 (2)	C12—C11—O2—C14	−176.9 (2)
C5—C4—C7—C8	135.3 (3)