2-Iodo-5-nitro-thio-phene.

The title compound, C(4)H(2)INO(2)S, was synthesized by nitration of iodo-thio-phene with acetyl nitrate. The molecule is essentially planar, withthe nitro group tilted by 1.78 (19)° and the iodine atom displaced by 0.0233 (2) Å with respect to the thiophene ring. In the crystal structure, adjacent mol-ecules are linked through weak I⋯O inter-actions [3.039 (2)Å], forming chains extending along the b axis.

Related literature

For the bioactivity of thio­phene derivatives, see: Wilson et al. (2010 ▶); Rudra et al. (2007 ▶); Altman et al. (2008 ▶); Morley et al. (2006 ▶).

Experimental

Crystal data

C4H2INO2S

M = 255.03

Monoclinic,

a = 9.195 (2) Å

b = 9.727 (2) Å

c = 7.6714 (17) Å

β = 105.043 (4)°

V = 662.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 5.07 mm−1

T = 110 K

0.48 × 0.29 × 0.08 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.195, T max = 0.687

3264 measured reflections

1419 independent reflections

1294 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.065

S = 1.09

1419 reflections

82 parameters

H-atom parameters constrained

Δρmax = 1.65 e Å−3

Δρmin = −1.07 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017356/rz2440sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017356/rz2440Isup2.hkl

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

C4H2INO2S	F(000) = 472
Mr = 255.03	Dx = 2.556 Mg m−3
Monoclinic, P21/c	Melting point: 348 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.195 (2) Å	Cell parameters from 2600 reflections
b = 9.727 (2) Å	θ = 2.3–27.0°
c = 7.6714 (17) Å	µ = 5.07 mm−1
β = 105.043 (4)°	T = 110 K
V = 662.6 (2) Å3	Plate, pale yellow
Z = 4	0.48 × 0.29 × 0.08 mm

Bruker SMART 1K CCD area-detector diffractometer	1419 independent reflections
Radiation source: fine-focus sealed tube	1294 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.195, Tmax = 0.687	k = −12→6
3264 measured reflections	l = −9→9

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.2502P] where P = (Fo2 + 2Fc2)/3
1419 reflections	(Δ/σ)max = 0.001
82 parameters	Δρmax = 1.65 e Å−3
0 restraints	Δρmin = −1.07 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.742893 (19)	0.45070 (2)	−0.00911 (2)	0.01661 (11)
S1	0.63408 (8)	0.77403 (7)	−0.09375 (9)	0.01554 (17)
C1	0.7728 (3)	0.6618 (3)	0.0128 (3)	0.0154 (6)
O2	0.5694 (3)	1.06507 (19)	−0.1375 (3)	0.0224 (5)
N1	0.6975 (3)	1.0473 (2)	−0.0419 (3)	0.0173 (5)
C2	0.9003 (3)	0.7266 (3)	0.1129 (4)	0.0176 (6)
H2	0.9873	0.6796	0.1805	0.021*
C3	0.8865 (3)	0.8712 (3)	0.1034 (3)	0.0171 (6)
H3	0.9627	0.9336	0.1630	0.021*
O1	0.7865 (3)	1.1411 (2)	0.0229 (3)	0.0257 (5)
C4	0.7496 (3)	0.9090 (4)	−0.0027 (3)	0.0148 (6)

	U11	U22	U33	U12	U13	U23
I1	0.02192 (16)	0.00881 (16)	0.01937 (15)	0.00103 (5)	0.00585 (10)	0.00003 (5)
S1	0.0171 (4)	0.0104 (3)	0.0176 (3)	0.0009 (2)	0.0018 (3)	−0.0006 (2)
C1	0.0216 (14)	0.0082 (14)	0.0184 (14)	0.0040 (10)	0.0087 (11)	0.0022 (9)
O2	0.0232 (12)	0.0178 (10)	0.0254 (11)	0.0056 (8)	0.0047 (9)	0.0048 (8)
N1	0.0215 (15)	0.0148 (13)	0.0163 (12)	0.0016 (9)	0.0060 (11)	0.0011 (8)
C2	0.0165 (14)	0.0168 (13)	0.0196 (14)	0.0021 (10)	0.0046 (11)	0.0006 (10)
C3	0.0176 (14)	0.0132 (13)	0.0201 (14)	−0.0027 (10)	0.0042 (11)	−0.0028 (10)
O1	0.0331 (12)	0.0094 (11)	0.0324 (12)	−0.0033 (9)	0.0044 (10)	−0.0019 (8)
C4	0.0206 (18)	0.0087 (16)	0.0167 (16)	−0.0007 (9)	0.0079 (13)	−0.0021 (8)

I1—C1	2.073 (3)	N1—C4	1.433 (4)
S1—C1	1.716 (3)	C2—C3	1.412 (4)
S1—C4	1.719 (3)	C2—H2	0.9500
C1—C2	1.376 (4)	C3—C4	1.361 (4)
O2—N1	1.227 (4)	C3—H3	0.9500
N1—O1	1.241 (3)
C1—S1—C4	89.32 (14)	C1—C2—H2	124.0
C2—C1—S1	113.2 (2)	C3—C2—H2	124.0
C2—C1—I1	125.1 (2)	C4—C3—C2	110.9 (3)
S1—C1—I1	121.68 (16)	C4—C3—H3	124.5
O2—N1—O1	124.5 (2)	C2—C3—H3	124.5
O2—N1—C4	118.3 (2)	C3—C4—N1	125.9 (3)
O1—N1—C4	117.2 (3)	C3—C4—S1	114.5 (3)
C1—C2—C3	112.0 (3)	N1—C4—S1	119.59 (19)
C4—S1—C1—C2	0.2 (2)	O2—N1—C4—C3	−178.6 (2)
C4—S1—C1—I1	179.18 (13)	O1—N1—C4—C3	1.9 (4)
S1—C1—C2—C3	−0.2 (3)	O2—N1—C4—S1	1.5 (3)
I1—C1—C2—C3	−179.22 (17)	O1—N1—C4—S1	−178.06 (17)
C1—C2—C3—C4	0.2 (3)	C1—S1—C4—C3	0.0 (2)
C2—C3—C4—N1	180.0 (2)	C1—S1—C4—N1	179.92 (18)
C2—C3—C4—S1	−0.1 (3)