2-Iodo-1,3-dimethoxy-benzene.

Crystals of the title compound, C(8)H(9)IO(2), were obtained from a dimethyl sulfoxide solution of 2,6-dimethoxy-benzoic acid and iodo-benzene diacetate under a nitro-gen atmosphere at 353 K. In the crystal structure, mol-ecules are linked by weak C-H⋯π inter-actions, generating inter-penetrating one-dimensional chains of perpendicularly oriented mol-ecules extending along [011] and [01]. Chains are also formed through non-bonding C-I⋯π contacts extending in the same directions, projecting a zigzag motif in view down [100]. The I⋯Cg distance is 3.695 (2) Å and the C-I⋯Cg angle is 164.17 (14)°. The mol-ecular symmetry m coincides with the mirror plane of the space group Cmc2(1), resulting in a half-mol-ecule in the asymmetric unit (Z' = ½).

Related literature

For the development of a deca­rboxylative palladation reaction and its use in a Heck-type olefination of arene carboxyl­ates, see: Myers et al. (2002 ▶). For a novel system for deca­rboxylative bromination, see: Telvekar & Chettiar (2007 ▶). For related structures, see: Kirsop et al. (2004 ▶); Ali et al. (2008 ▶). For a database study of C-halogen–π inter­actions and their influence on mol­ecular conformation and crystal packing, see: Prasanna & Guru Row (2000 ▶). For structure validation in chemical crystallography, see: Spek (2009 ▶).

Experimental

Crystal data

C8H9IO2

M = 264.05

Orthorhombic,

a = 12.5767 (13) Å

b = 8.6788 (8) Å

c = 8.4338 (9) Å

V = 920.55 (16) Å3

Z = 4

Mo Kα radiation

μ = 3.43 mm−1

T = 296 K

0.23 × 0.19 × 0.16 mm

Data collection

Bruker P4 diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.500, T max = 0.616 (expected range = 0.469–0.578)

2731 measured reflections

850 independent reflections

840 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.046

S = 1.12

850 reflections

55 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.02 e Å−3

Δρmin = −0.84 e Å−3

Absolute structure: Flack (1983 ▶), 362 Friedel pairs

Flack parameter: −0.05 (4)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025264/si2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025264/si2185Isup2.hkl

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

C8H9IO2	F(000) = 504
Mr = 264.05	Dx = 1.905 Mg m−3
Orthorhombic, Cmc21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 1365 reflections
a = 12.5767 (13) Å	θ = 3.7–27.5°
b = 8.6788 (8) Å	µ = 3.43 mm−1
c = 8.4338 (9) Å	T = 296 K
V = 920.55 (16) Å3	Prism, white
Z = 4	0.23 × 0.19 × 0.16 mm

Bruker P4 diffractometer	850 independent reflections
Radiation source: fine-focus sealed tube	840 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 25.5°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −15→15
Tmin = 0.500, Tmax = 0.616	k = −10→7
2731 measured reflections	l = −9→10

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)] = 0.019	H-atom parameters constrained
wR(F2) = 0.046	w = 1/[σ2(Fo2) + (0.0245P)2 + 0.6278P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
850 reflections	Δρmax = 1.02 e Å−3
55 parameters	Δρmin = −0.84 e Å−3
1 restraint	Absolute structure: Flack (1983), 362 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (4)

	x	y	z	Uiso*/Ueq
I1	1.0000	0.95668 (3)	0.54168 (9)	0.04533 (12)
O1	0.8137 (2)	0.7922 (4)	0.7118 (3)	0.0562 (8)
C1	1.0000	0.5564 (7)	0.9408 (11)	0.073 (2)
H1A	1.0000	0.4784	1.0163	0.088*
C2	0.9046 (4)	0.6130 (5)	0.8860 (6)	0.0637 (12)
H2A	0.8409	0.5739	0.9250	0.076*
C3	0.9038 (3)	0.7287 (4)	0.7725 (4)	0.0432 (9)
C4	1.0000	0.7859 (5)	0.7165 (6)	0.0374 (11)
C5	0.7137 (4)	0.7340 (7)	0.7685 (7)	0.0776 (16)
H5A	0.6566	0.7868	0.7160	0.116*
H5B	0.7087	0.7505	0.8808	0.116*
H5C	0.7091	0.6256	0.7464	0.116*

	U11	U22	U33	U12	U13	U23
I1	0.04655 (17)	0.05029 (18)	0.0391 (2)	0.000	0.000	0.01194 (17)
O1	0.0454 (16)	0.0700 (18)	0.0531 (19)	−0.0124 (14)	0.0033 (14)	0.0111 (15)
C1	0.099 (6)	0.052 (4)	0.068 (5)	0.000	0.000	0.030 (3)
C2	0.085 (3)	0.051 (2)	0.055 (3)	−0.016 (2)	0.009 (2)	0.014 (2)
C3	0.058 (2)	0.0384 (16)	0.033 (2)	−0.0055 (16)	0.0005 (16)	−0.0015 (15)
C4	0.055 (3)	0.030 (2)	0.027 (3)	0.000	0.000	−0.0008 (19)
C5	0.056 (3)	0.086 (4)	0.091 (5)	−0.023 (3)	0.010 (3)	0.007 (3)

I1—C4	2.090 (5)	C2—H2A	0.9300
O1—C3	1.359 (5)	C3—C4	1.391 (5)
O1—C5	1.437 (6)	C4—C3i	1.391 (5)
C1—C2	1.376 (6)	C5—H5A	0.9600
C1—C2i	1.376 (6)	C5—H5B	0.9600
C1—H1A	0.9300	C5—H5C	0.9600
C2—C3	1.388 (5)
C3—O1—C5	117.5 (4)	C3i—C4—C3	121.0 (5)
C2—C1—C2i	121.3 (6)	C3i—C4—I1	119.5 (2)
C2—C1—H1A	119.3	C3—C4—I1	119.5 (2)
C2i—C1—H1A	119.3	O1—C5—H5A	109.5
C1—C2—C3	119.8 (5)	O1—C5—H5B	109.5
C1—C2—H2A	120.1	H5A—C5—H5B	109.5
C3—C2—H2A	120.1	O1—C5—H5C	109.5
O1—C3—C2	124.0 (4)	H5A—C5—H5C	109.5
O1—C3—C4	116.9 (3)	H5B—C5—H5C	109.5
C2—C3—C4	119.1 (4)
C2i—C1—C2—C3	0.5 (11)	O1—C3—C4—C3i	179.6 (3)
C5—O1—C3—C2	−0.7 (6)	C2—C3—C4—C3i	0.1 (7)
C5—O1—C3—C4	179.9 (4)	O1—C3—C4—I1	−1.9 (5)
C1—C2—C3—O1	−179.7 (5)	C2—C3—C4—I1	178.6 (3)
C1—C2—C3—C4	−0.3 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cg1ii	0.93	2.94	3.824 (9)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cg1i	0.93	2.94	3.824 (9)	159

Symmetry code: (i) . Cg1 is the centroid of the C1–C4/C3A/C2A ring.