1,8-Diiodo-anthracene.

The mol-ecule of the title compound, C(14)H(8)I(2), an inter-mediate in the synthesis of organic materials, is nearly planar, the maximum deviation from the mean plane being 0.032 (1) Å for the C atoms and 0.082 (2) Å for the I atoms. In the crystal structure, a sandwich-herringbone arrangement of mol-ecules is observed, whereas a columnar π-stacking arrangement has been reported for the chlorinated congener 1,8-dichloro-anthracene. Similar effects of halogen substituents on the modulation of packing arrangements are reported for halogenated aromatic compounds such as tetra-cenes and chrycenes.

Related literature

For the synthesis, see: Lovell & Joule (1997 ▶); Goichi et al. (2005 ▶). For the crystal structure of related 1,8-dichloro­anthracenes, see: Desvergne et al., (1978 ▶); Benites et al., (1996 ▶). For similar halogen effects on the arrangement of aromatic mol­ecules, see: Moon et al. (2004 ▶); Isobe et al. (2009 ▶). For an example of synthetic utility of the title compound in organic materials, see: Nakanishi et al. (2010 ▶).

Experimental

Crystal data

C14H8I2

M = 430.00

Monoclinic,

a = 10.1167 (11) Å

b = 10.8680 (11) Å

c = 11.3930 (12) Å

β = 101.829 (1)°

V = 1226.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 5.10 mm−1

T = 100 K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.429, T max = 0.630

13646 measured reflections

2904 independent reflections

2783 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.014

wR(F 2) = 0.038

S = 1.09

2904 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, Yadokari-XG (Kabuto et al., 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035191/jh2197sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035191/jh2197Isup2.hkl

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

C14H8I2	F(000) = 792
Mr = 430.00	Dx = 2.330 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5335 reflections
a = 10.1167 (11) Å	θ = 2.6–27.8°
b = 10.8680 (11) Å	µ = 5.10 mm−1
c = 11.3930 (12) Å	T = 100 K
β = 101.829 (1)°	Cubic, green
V = 1226.0 (2) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2904 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	2783 reflections with I > 2σ(I)
Bruker Helios multilayer confocal mirror	Rint = 0.016
Detector resolution: 8.333 pixels mm-1	θmax = 27.9°, θmin = 2.1°
φ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.429, Tmax = 0.630	l = −14→14
13646 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)] = 0.014	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.038	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0197P)2 + 0.8912P] where P = (Fo2 + 2Fc2)/3
2904 reflections	(Δ/σ)max = 0.005
145 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.63 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-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	0.760513 (11)	1.050372 (9)	0.779962 (10)	0.01704 (4)
I2	0.242248 (11)	1.052601 (9)	0.591438 (9)	0.01734 (4)
C8	0.21957 (18)	0.93209 (15)	0.73076 (15)	0.0147 (3)
C9	0.46782 (17)	0.93129 (14)	0.81821 (14)	0.0138 (3)
H7	0.4839	0.9827	0.7552	0.017*
C13	0.33549 (17)	0.89456 (14)	0.81903 (14)	0.0136 (3)
C7	0.09231 (17)	0.89426 (16)	0.73555 (15)	0.0178 (3)
H6	0.0179	0.9195	0.6752	0.021*
C5	0.17608 (18)	0.77913 (15)	0.91729 (15)	0.0174 (3)
H4	0.1600	0.7278	0.9804	0.021*
C6	0.07051 (17)	0.81682 (16)	0.83110 (15)	0.0188 (3)
H5	−0.0185	0.7915	0.8344	0.023*
C14	0.31114 (17)	0.81568 (14)	0.91435 (14)	0.0144 (3)
C11	0.57708 (17)	0.89446 (14)	0.90752 (14)	0.0137 (3)
C12	0.55249 (17)	0.81532 (14)	1.00247 (14)	0.0146 (3)
C10	0.42066 (17)	0.77828 (15)	1.00274 (14)	0.0158 (3)
H8	0.4048	0.7258	1.0651	0.019*
C4	0.66292 (18)	0.77839 (15)	1.09544 (15)	0.0173 (3)
H3	0.6470	0.7262	1.1580	0.021*
C1	0.71420 (18)	0.93258 (15)	0.91241 (15)	0.0143 (3)
C2	0.81750 (17)	0.89582 (15)	1.00237 (15)	0.0171 (3)
H1	0.9071	0.9225	1.0032	0.020*
C3	0.79074 (18)	0.81744 (16)	1.09492 (15)	0.0186 (3)
H2	0.8631	0.7920	1.1572	0.022*

	U11	U22	U33	U12	U13	U23
I1	0.01809 (7)	0.01676 (6)	0.01754 (7)	−0.00121 (4)	0.00662 (5)	0.00173 (4)
I2	0.02054 (7)	0.01650 (7)	0.01391 (6)	0.00081 (4)	0.00105 (5)	0.00270 (3)
C8	0.0183 (8)	0.0134 (7)	0.0128 (7)	0.0009 (6)	0.0040 (6)	−0.0012 (5)
C9	0.0178 (7)	0.0117 (7)	0.0126 (7)	0.0006 (6)	0.0042 (6)	0.0000 (5)
C13	0.0178 (8)	0.0097 (7)	0.0139 (7)	0.0001 (6)	0.0045 (6)	−0.0019 (5)
C7	0.0160 (8)	0.0192 (8)	0.0173 (8)	0.0001 (6)	0.0015 (6)	−0.0039 (6)
C5	0.0231 (8)	0.0144 (7)	0.0163 (7)	−0.0032 (6)	0.0083 (6)	−0.0024 (6)
C6	0.0170 (8)	0.0199 (8)	0.0209 (8)	−0.0043 (6)	0.0069 (6)	−0.0057 (6)
C14	0.0193 (8)	0.0105 (7)	0.0141 (7)	−0.0005 (6)	0.0051 (6)	−0.0023 (6)
C11	0.0182 (8)	0.0100 (7)	0.0134 (7)	0.0015 (6)	0.0048 (6)	−0.0012 (5)
C12	0.0200 (8)	0.0104 (7)	0.0135 (7)	0.0015 (6)	0.0040 (6)	−0.0008 (6)
C10	0.0225 (8)	0.0116 (7)	0.0145 (7)	0.0006 (6)	0.0063 (6)	0.0012 (6)
C4	0.0245 (8)	0.0130 (7)	0.0141 (7)	0.0045 (6)	0.0032 (6)	0.0018 (6)
C1	0.0182 (8)	0.0114 (7)	0.0145 (7)	0.0022 (6)	0.0060 (6)	−0.0017 (5)
C2	0.0162 (8)	0.0168 (8)	0.0179 (8)	0.0019 (6)	0.0026 (6)	−0.0030 (6)
C3	0.0218 (8)	0.0170 (8)	0.0152 (7)	0.0052 (6)	−0.0006 (6)	−0.0009 (6)

I1—C1	2.1037 (17)	C6—H5	0.9500
I2—C8	2.1064 (17)	C14—C10	1.396 (2)
C8—C7	1.363 (2)	C11—C1	1.438 (2)
C8—C13	1.439 (2)	C11—C12	1.443 (2)
C9—C11	1.399 (2)	C12—C10	1.394 (2)
C9—C13	1.399 (2)	C12—C4	1.430 (2)
C9—H7	0.9500	C10—H8	0.9500
C13—C14	1.444 (2)	C4—C3	1.362 (3)
C7—C6	1.428 (2)	C4—H3	0.9500
C7—H6	0.9500	C1—C2	1.365 (2)
C5—C6	1.357 (3)	C2—C3	1.424 (2)
C5—C14	1.430 (2)	C2—H1	0.9500
C5—H4	0.9500	C3—H2	0.9500
C7—C8—C13	121.86 (16)	C9—C11—C1	123.92 (15)
C7—C8—I2	117.86 (12)	C9—C11—C12	118.95 (15)
C13—C8—I2	120.26 (12)	C1—C11—C12	117.12 (15)
C11—C9—C13	121.88 (15)	C10—C12—C4	121.32 (15)
C11—C9—H7	119.1	C10—C12—C11	119.07 (15)
C13—C9—H7	119.1	C4—C12—C11	119.60 (15)
C9—C13—C8	123.96 (15)	C12—C10—C14	122.18 (15)
C9—C13—C14	119.05 (15)	C12—C10—H8	118.9
C8—C13—C14	116.99 (15)	C14—C10—H8	118.9
C8—C7—C6	120.19 (16)	C3—C4—C12	120.49 (15)
C8—C7—H6	119.9	C3—C4—H3	119.8
C6—C7—H6	119.9	C12—C4—H3	119.8
C6—C5—C14	120.88 (15)	C2—C1—C11	121.93 (15)
C6—C5—H4	119.6	C2—C1—I1	117.90 (13)
C14—C5—H4	119.6	C11—C1—I1	120.17 (12)
C5—C6—C7	120.50 (16)	C1—C2—C3	119.90 (16)
C5—C6—H5	119.8	C1—C2—H1	120.0
C7—C6—H5	119.8	C3—C2—H1	120.0
C10—C14—C5	121.54 (15)	C4—C3—C2	120.95 (16)
C10—C14—C13	118.87 (15)	C4—C3—H2	119.5
C5—C14—C13	119.59 (15)	C2—C3—H2	119.5
C11—C9—C13—C8	178.61 (15)	C9—C11—C12—C10	−0.2 (2)
C11—C9—C13—C14	−0.4 (2)	C1—C11—C12—C10	178.63 (14)
C7—C8—C13—C9	−179.73 (16)	C9—C11—C12—C4	−179.06 (15)
I2—C8—C13—C9	−1.4 (2)	C1—C11—C12—C4	−0.2 (2)
C7—C8—C13—C14	−0.7 (2)	C4—C12—C10—C14	178.48 (15)
I2—C8—C13—C14	177.65 (11)	C11—C12—C10—C14	−0.3 (2)
C13—C8—C7—C6	1.1 (2)	C5—C14—C10—C12	−178.59 (15)
I2—C8—C7—C6	−177.28 (12)	C13—C14—C10—C12	0.5 (2)
C14—C5—C6—C7	−0.1 (3)	C10—C12—C4—C3	−178.73 (16)
C8—C7—C6—C5	−0.7 (3)	C11—C12—C4—C3	0.1 (2)
C6—C5—C14—C10	179.61 (16)	C9—C11—C1—C2	178.97 (16)
C6—C5—C14—C13	0.5 (2)	C12—C11—C1—C2	0.2 (2)
C9—C13—C14—C10	−0.1 (2)	C9—C11—C1—I1	−0.2 (2)
C8—C13—C14—C10	−179.24 (14)	C12—C11—C1—I1	−178.97 (11)
C9—C13—C14—C5	178.98 (15)	C11—C1—C2—C3	0.0 (2)
C8—C13—C14—C5	−0.1 (2)	I1—C1—C2—C3	179.15 (12)
C13—C9—C11—C1	−178.17 (15)	C12—C4—C3—C2	0.1 (2)
C13—C9—C11—C12	0.6 (2)	C1—C2—C3—C4	−0.1 (2)