3,6-Diiodo-9H-carbazole.

In the title compound, C(12)H(7)I(2)N, the tricyclic aromatic ring system is essentially planar, with an r.m.s. deviation of 0.0272 Å. The two I atoms are marginally out of plane, with the C-I bonds angled at 3.9 (2) and 1.1 (2)° with respect to the planes of their respective benzene rings, above and below the plane of the carbazole ring system. No classical hydrogen bonds are observed in the crystal structure.

Related literature

For the synthesis of the title compound, see: Tucker (1926 ▶); Lengvinaite et al. (2007 ▶). For related compounds, see: Grigalevicius et al. (2007 ▶); Cui et al. (2009 ▶); Tian et al. (2010 ▶); Klejevskaja et al. (2007 ▶). For their applications, see: Zhang et al. (2009 ▶); Zhong’an et al. (2010 ▶); Lu et al. (2006 ▶); Grigalev­icius et al. (2006 ▶, 2011 ▶).

Experimental

Crystal data

C12H7I2N

M = 418.99

Orthorhombic,

a = 11.8823 (14) Å

b = 7.8835 (9) Å

c = 24.835 (3) Å

V = 2326.4 (5) Å3

Z = 8

Mo Kα radiation

μ = 5.37 mm−1

T = 293 K

0.23 × 0.21 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.371, T max = 0.445

12303 measured reflections

2456 independent reflections

1879 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.052

S = 1.05

2456 reflections

141 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012901/pk2397sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812012901/pk2397Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012901/pk2397Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812012901/pk2397Isup4.cml

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

C12H7I2N	F(000) = 1536
Mr = 418.99	Dx = 2.392 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 12303 reflections
a = 11.8823 (14) Å	θ = 1.6–26.8°
b = 7.8835 (9) Å	µ = 5.37 mm−1
c = 24.835 (3) Å	T = 293 K
V = 2326.4 (5) Å3	Block, colorless
Z = 8	0.23 × 0.21 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	2456 independent reflections
Radiation source: fine-focus sealed tube	1879 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 26.8°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→15
Tmin = 0.371, Tmax = 0.445	k = −9→9
12303 measured reflections	l = −31→29

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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.052	w = 1/[σ2(Fo2) + (0.0193P)2 + 0.8116P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
2456 reflections	Δρmax = 0.57 e Å−3
141 parameters	Δρmin = −0.56 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00021 (4)

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
C11	0.7583 (3)	0.4740 (4)	0.77946 (15)	0.0445 (9)
H11	0.8290	0.5240	0.7822	0.053*
C12	0.6978 (3)	0.4308 (4)	0.82476 (14)	0.0406 (9)
H12	0.7277	0.4525	0.8587	0.049*
H1N	0.807 (3)	0.511 (4)	0.6716 (13)	0.032 (11)*
I2	0.35650 (2)	0.22435 (4)	0.536173 (10)	0.06040 (11)
I1	0.50690 (2)	0.28678 (4)	0.891514 (9)	0.04915 (10)
N1	0.7525 (3)	0.4684 (4)	0.67876 (13)	0.0460 (8)
C5	0.4904 (3)	0.2882 (4)	0.63769 (13)	0.0387 (8)
H5	0.4264	0.2467	0.6548	0.046*
C4	0.5818 (3)	0.3460 (4)	0.66751 (12)	0.0333 (8)
C6	0.4967 (3)	0.2939 (5)	0.58238 (14)	0.0432 (9)
C9	0.6766 (3)	0.4125 (4)	0.64077 (14)	0.0402 (9)
C1	0.5918 (3)	0.3545 (4)	0.82033 (13)	0.0373 (8)
C2	0.5437 (3)	0.3208 (4)	0.77121 (13)	0.0357 (8)
H2	0.4730	0.2705	0.7690	0.043*
C3	0.6032 (3)	0.3638 (4)	0.72449 (12)	0.0333 (8)
C8	0.6826 (3)	0.4177 (5)	0.58496 (14)	0.0478 (10)
H8	0.7461	0.4603	0.5677	0.057*
C7	0.5931 (3)	0.3587 (5)	0.55598 (14)	0.0492 (10)
H7	0.5954	0.3612	0.5186	0.059*
C10	0.7105 (3)	0.4408 (4)	0.72961 (14)	0.0375 (8)

	U11	U22	U33	U12	U13	U23
C11	0.033 (2)	0.047 (2)	0.054 (2)	−0.0035 (18)	0.0000 (19)	−0.0083 (18)
C12	0.040 (2)	0.043 (2)	0.0391 (19)	0.0011 (17)	−0.0046 (17)	−0.0074 (16)
I2	0.0586 (2)	0.0815 (2)	0.04106 (16)	−0.00842 (15)	−0.01063 (13)	0.00035 (13)
I1	0.04885 (17)	0.06034 (18)	0.03825 (14)	−0.00679 (13)	0.00108 (12)	0.00815 (11)
N1	0.0340 (19)	0.055 (2)	0.0490 (18)	−0.0110 (17)	0.0093 (18)	0.0011 (16)
C5	0.036 (2)	0.040 (2)	0.039 (2)	0.0034 (17)	0.0027 (17)	0.0040 (16)
C4	0.034 (2)	0.0312 (18)	0.0345 (18)	0.0029 (15)	0.0017 (16)	0.0029 (14)
C6	0.044 (2)	0.048 (2)	0.0375 (19)	−0.0003 (19)	−0.0025 (17)	−0.0026 (17)
C9	0.036 (2)	0.043 (2)	0.042 (2)	0.0021 (17)	0.0030 (17)	0.0004 (16)
C1	0.038 (2)	0.0355 (19)	0.0385 (18)	0.0031 (17)	0.0052 (17)	0.0040 (16)
C2	0.0298 (18)	0.034 (2)	0.0427 (19)	−0.0003 (15)	−0.0044 (16)	0.0050 (15)
C3	0.0312 (19)	0.0328 (19)	0.0358 (18)	0.0010 (15)	0.0002 (15)	0.0010 (14)
C8	0.041 (2)	0.061 (3)	0.041 (2)	0.003 (2)	0.0151 (18)	0.0017 (18)
C7	0.055 (3)	0.059 (3)	0.0341 (19)	0.005 (2)	0.0050 (19)	−0.0020 (17)
C10	0.0331 (19)	0.037 (2)	0.043 (2)	0.0003 (16)	0.0043 (17)	−0.0027 (16)

C11—C12	1.378 (5)	C5—H5	0.9300
C11—C10	1.387 (5)	C4—C9	1.409 (5)
C11—H11	0.9300	C4—C3	1.445 (4)
C12—C1	1.400 (5)	C6—C7	1.415 (5)
C12—H12	0.9300	C9—C8	1.389 (5)
I2—C6	2.096 (4)	C1—C2	1.373 (4)
I1—C1	2.104 (3)	C2—C3	1.400 (4)
N1—C10	1.375 (4)	C2—H2	0.9300
N1—C9	1.378 (5)	C3—C10	1.418 (5)
N1—H1N	0.75 (3)	C8—C7	1.366 (5)
C5—C6	1.376 (5)	C8—H8	0.9300
C5—C4	1.391 (5)	C7—H7	0.9300
C12—C11—C10	117.9 (3)	C8—C9—C4	121.5 (3)
C12—C11—H11	121.0	C2—C1—C12	121.8 (3)
C10—C11—H11	121.0	C2—C1—I1	119.8 (3)
C11—C12—C1	120.8 (3)	C12—C1—I1	118.3 (3)
C11—C12—H12	119.6	C1—C2—C3	118.6 (3)
C1—C12—H12	119.6	C1—C2—H2	120.7
C10—N1—C9	109.9 (3)	C3—C2—H2	120.7
C10—N1—H1N	127 (3)	C2—C3—C10	118.9 (3)
C9—N1—H1N	123 (3)	C2—C3—C4	134.4 (3)
C6—C5—C4	118.5 (3)	C10—C3—C4	106.7 (3)
C6—C5—H5	120.7	C7—C8—C9	118.4 (4)
C4—C5—H5	120.7	C7—C8—H8	120.8
C5—C4—C9	119.7 (3)	C9—C8—H8	120.8
C5—C4—C3	133.7 (3)	C8—C7—C6	120.6 (3)
C9—C4—C3	106.6 (3)	C8—C7—H7	119.7
C5—C6—C7	121.2 (3)	C6—C7—H7	119.7
C5—C6—I2	119.6 (3)	N1—C10—C11	129.9 (3)
C7—C6—I2	118.9 (3)	N1—C10—C3	108.2 (3)
N1—C9—C8	129.8 (3)	C11—C10—C3	121.9 (3)
N1—C9—C4	108.7 (3)
C10—C11—C12—C1	0.5 (5)	C5—C4—C3—C2	4.6 (7)
C6—C5—C4—C9	1.7 (5)	C9—C4—C3—C2	−179.0 (4)
C6—C5—C4—C3	177.7 (4)	C5—C4—C3—C10	−176.4 (4)
C4—C5—C6—C7	−0.8 (5)	C9—C4—C3—C10	0.1 (4)
C4—C5—C6—I2	−175.7 (2)	N1—C9—C8—C7	−177.6 (4)
C10—N1—C9—C8	178.7 (4)	C4—C9—C8—C7	1.0 (5)
C10—N1—C9—C4	0.0 (4)	C9—C8—C7—C6	−0.1 (6)
C5—C4—C9—N1	177.0 (3)	C5—C6—C7—C8	0.0 (6)
C3—C4—C9—N1	0.0 (4)	I2—C6—C7—C8	174.9 (3)
C5—C4—C9—C8	−1.8 (5)	C9—N1—C10—C11	178.8 (4)
C3—C4—C9—C8	−178.8 (3)	C9—N1—C10—C3	0.0 (4)
C11—C12—C1—C2	−0.4 (5)	C12—C11—C10—N1	−179.0 (4)
C11—C12—C1—I1	178.5 (3)	C12—C11—C10—C3	−0.4 (5)
C12—C1—C2—C3	0.3 (5)	C2—C3—C10—N1	179.1 (3)
I1—C1—C2—C3	−178.6 (2)	C4—C3—C10—N1	−0.1 (4)
C1—C2—C3—C10	−0.2 (5)	C2—C3—C10—C11	0.3 (5)
C1—C2—C3—C4	178.7 (4)	C4—C3—C10—C11	−178.9 (3)