9,10-Diiodo-phenanthrene.

The whole mol-ecule of the title compound, C14H8I2, is generated by crystallographic twofold symmetry. The mol-ecule is planar [maximum deviation = 0.0323 (6) Å] with the I atoms displaced from the mean plane of the phenanthrene ring system by only 0.0254 (5) Å. In the crystal, mol-ecules form face-to-face slipped anti-parallel π-π stacking inter-actions along the c axis with an inter-planar distance of 3.499 (7) Å.

Related literature

For the synthesis of the title compound, see: Rodrígeuz-Lojo et al. (2012 ▶). For a related structure, see: Yokota et al. (2012 ▶).

Experimental

Crystal data

C14H8I2

M = 430

Monoclinic,

a = 18.094 (2) Å

b = 9.4557 (14) Å

c = 7.4187 (10) Å

β = 111.953 (3)°

V = 1177.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 5.31 mm−1

T = 223 K

0.52 × 0.08 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.388, T max = 0.869

5595 measured reflections

1345 independent reflections

1077 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.083

S = 1.12

1345 reflections

73 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −0.92 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1999 ▶); cell refinement: PROCESS-AUTO (Rigaku, 1998 ▶); data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045758/jj2155sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045758/jj2155Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045758/jj2155Isup3.cml

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

C14H8I2	F(000) = 792
Mr = 430	Dx = 2.426 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3465 reflections
a = 18.094 (2) Å	θ = 3.1–27.5°
b = 9.4557 (14) Å	µ = 5.31 mm−1
c = 7.4187 (10) Å	T = 223 K
β = 111.953 (3)°	Needle, colorless
V = 1177.2 (3) Å3	0.52 × 0.08 × 0.05 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	1345 independent reflections
Radiation source: fine-focus sealed x-ray tube	1077 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 10 pixels mm-1	θmax = 27.5°, θmin = 3.5°
ω scans	h = −23→22
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
Tmin = 0.388, Tmax = 0.869	l = −8→9
5595 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0077P)2 + 13.1956P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
1345 reflections	Δρmax = 0.92 e Å−3
73 parameters	Δρmin = −0.92 e Å−3
0 restraints

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.3399 (3)	0.4417 (6)	0.4793 (7)	0.0368 (12)
H1	0.3127	0.3564	0.4332	0.044*
C2	0.3020 (3)	0.5667 (8)	0.4155 (8)	0.0470 (15)
H2	0.2488	0.5669	0.3275	0.056*
C3	0.3408 (3)	0.6927 (7)	0.4781 (9)	0.0467 (15)
H3	0.3146	0.7786	0.4306	0.056*
C4	0.4171 (4)	0.6931 (6)	0.6089 (8)	0.0424 (13)
H4	0.4426	0.78	0.6529	0.051*
C5	0.4587 (3)	0.5675 (5)	0.6798 (7)	0.0289 (10)
C6	0.4192 (3)	0.4383 (5)	0.6137 (7)	0.0261 (9)
C7	0.4618 (3)	0.3079 (5)	0.6846 (7)	0.0281 (10)
I1	0.40244 (3)	0.11933 (4)	0.58098 (7)	0.05783 (18)

	U11	U22	U33	U12	U13	U23
C1	0.029 (2)	0.051 (3)	0.029 (3)	0.003 (2)	0.008 (2)	0.001 (2)
C2	0.026 (3)	0.078 (4)	0.034 (3)	0.012 (3)	0.007 (2)	0.010 (3)
C3	0.038 (3)	0.057 (4)	0.048 (3)	0.024 (3)	0.019 (3)	0.020 (3)
C4	0.048 (3)	0.040 (3)	0.048 (3)	0.012 (2)	0.028 (3)	0.008 (3)
C5	0.030 (2)	0.030 (2)	0.031 (3)	0.0021 (19)	0.017 (2)	0.0012 (19)
C6	0.023 (2)	0.035 (2)	0.024 (2)	0.0010 (18)	0.0126 (18)	0.0001 (18)
C7	0.033 (2)	0.026 (2)	0.025 (2)	−0.0029 (18)	0.010 (2)	−0.0020 (18)
I1	0.0670 (3)	0.0402 (2)	0.0526 (3)	−0.01527 (19)	0.0067 (2)	−0.00726 (18)

C1—C2	1.359 (8)	C4—C5	1.399 (7)
C1—C6	1.409 (7)	C4—H4	0.94
C1—H1	0.94	C5—C6	1.408 (7)
C2—C3	1.372 (9)	C5—C5i	1.467 (10)
C2—H2	0.94	C6—C7	1.445 (6)
C3—C4	1.359 (8)	C7—C7i	1.360 (9)
C3—H3	0.94	C7—I1	2.075 (5)
C2—C1—C6	120.9 (5)	C5—C4—H4	119.1
C2—C1—H1	119.6	C4—C5—C6	118.2 (5)
C6—C1—H1	119.6	C4—C5—C5i	121.9 (3)
C1—C2—C3	120.7 (5)	C6—C5—C5i	119.8 (3)
C1—C2—H2	119.7	C5—C6—C1	118.5 (5)
C3—C2—H2	119.7	C5—C6—C7	118.7 (4)
C4—C3—C2	119.9 (5)	C1—C6—C7	122.8 (5)
C4—C3—H3	120.1	C7i—C7—C6	121.5 (3)
C2—C3—H3	120.1	C7i—C7—I1	120.77 (13)
C3—C4—C5	121.8 (6)	C6—C7—I1	117.8 (3)
C3—C4—H4	119.1
C6—C1—C2—C3	1.1 (8)	C5i—C5—C6—C7	−0.9 (8)
C1—C2—C3—C4	−1.6 (9)	C2—C1—C6—C5	−0.4 (7)
C2—C3—C4—C5	1.4 (9)	C2—C1—C6—C7	−179.6 (5)
C3—C4—C5—C6	−0.7 (8)	C5—C6—C7—C7i	1.2 (8)
C3—C4—C5—C5i	179.7 (6)	C1—C6—C7—C7i	−179.6 (6)
C4—C5—C6—C1	0.2 (7)	C5—C6—C7—I1	−179.0 (3)
C5i—C5—C6—C1	179.8 (5)	C1—C6—C7—I1	0.2 (6)
C4—C5—C6—C7	179.5 (5)