2-Iodo-N-(2-nitro-phenyl-sulfan-yl)aniline.

In title compound, C(12)H(9)IN(2)O(2)S, the nitro group is rotated slightly, by 8.91 (3)°, out of the plane of the aromatic ring to which it is bonded. Between the two aromatic rings the CSN plane is at a dihedral angle of 84.0 (7)° to the HNC plane. Mol-ecules are linked by C-H⋯O inter-actions into a double helical supra-molecular architecture. There are no iodo-nitro, π-π or C-H⋯π(arene) inter-actions.

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Brito et al. (2004 ▶, 2005 ▶, 2006 ▶); Glidewell et al. (2003 ▶); Kuhle (1973 ▶); Pauling (1960 ▶).

Experimental

Crystal data

C12H9IN2O2S

M = 372.17

Trigonal,

a = 28.6221 (12) Å

c = 8.4062 (17) Å

V = 5963.9 (13) Å3

Z = 18

Mo Kα radiation

μ = 2.57 mm−1

T = 298 (2) K

0.47 × 0.32 × 0.20 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.380, T max = 0.600

11358 measured reflections

3251 independent reflections

2801 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.205

S = 1.21

3251 reflections

166 parameters

H-atom parameters constrained

Δρmax = 1.04 e Å−3

Δρmin = −1.05 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019491/fl2204sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019491/fl2204Isup2.hkl

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

C12H9IN2O2S	Z = 18
Mr = 372.17	F000 = 3240
Trigonal, R3	Dx = 1.865 Mg m−3
Hall symbol: -R 3	Melting point: 472 K
a = 28.6221 (12) Å	Mo Kα radiation λ = 0.71073 Å
b = 28.6221 (12) Å	Cell parameters from 909 reflections
c = 8.4062 (17) Å	θ = 1.4–28.5º
α = 90º	µ = 2.57 mm−1
β = 90º	T = 298 (2) K
γ = 120º	Prism, yellow
V = 5963.9 (13) Å3	0.47 × 0.32 × 0.20 mm

Nonius KappaCCD area-detector diffractometer	2801 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Monochromator: graphite	θmax = 28.5º
φ scans, and ω scans with κ offsets	θmin = 1.4º
Absorption correction: multi-scan(SORTAV; Blessing, 1995)	h = −31→37
Tmin = 0.380, Tmax = 0.600	k = −36→35
11358 measured reflections	l = −7→11
3251 independent reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.087P)2 + 39.1076P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.072	(Δ/σ)max = 0.001
wR(F2) = 0.205	Δρmax = 1.04 e Å−3
S = 1.21	Δρmin = −1.05 e Å−3
3251 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
166 parameters	Extinction coefficient: 0.0064 (7)

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	1.003222 (18)	0.07997 (2)	0.27240 (7)	0.0680 (3)
S1	0.81458 (6)	−0.00495 (6)	0.12352 (17)	0.0458 (4)
N1	0.8810 (2)	0.0367 (2)	0.1625 (7)	0.0565 (13)
H1	0.9042	0.0289	0.1244	0.068*
N2	0.70588 (19)	−0.0418 (2)	−0.0484 (7)	0.0529 (12)
O1	0.7146 (2)	−0.0679 (2)	0.0488 (7)	0.0679 (13)
O2	0.6610 (2)	−0.0547 (3)	−0.0985 (9)	0.0865 (19)
C1	0.9522 (2)	0.1110 (2)	0.3204 (7)	0.0450 (12)
C2	0.8998 (2)	0.0847 (2)	0.2574 (6)	0.0427 (11)
C3	0.8677 (3)	0.1073 (3)	0.2903 (7)	0.0498 (13)
H3	0.8328	0.0909	0.25	0.06*
C4	0.8862 (3)	0.1532 (3)	0.3809 (8)	0.0559 (15)
H4	0.8642	0.1679	0.3997	0.067*
C5	0.9383 (3)	0.1777 (3)	0.4448 (8)	0.0596 (17)
H5	0.9507	0.2083	0.5081	0.072*
C6	0.9706 (3)	0.1569 (2)	0.4143 (7)	0.0518 (14)
H6	1.0053	0.1733	0.4562	0.062*
C7	0.80300 (19)	0.02629 (18)	−0.0433 (6)	0.0340 (9)
C8	0.75198 (19)	0.00701 (19)	−0.1113 (6)	0.0365 (10)
C9	0.7438 (2)	0.0326 (3)	−0.2401 (7)	0.0482 (13)
H9	0.7093	0.0191	−0.2816	0.058*
C10	0.7861 (3)	0.0775 (3)	−0.3060 (7)	0.0549 (15)
H10	0.7809	0.0938	−0.3946	0.066*
C11	0.8368 (3)	0.0982 (2)	−0.2383 (7)	0.0495 (13)
H11	0.8656	0.1294	−0.2798	0.059*
C12	0.8450 (2)	0.0729 (2)	−0.1094 (6)	0.0391 (10)
H12	0.8795	0.0875	−0.0663	0.047*

	U11	U22	U33	U12	U13	U23
I1	0.0502 (3)	0.0627 (4)	0.0973 (5)	0.0329 (2)	−0.0026 (2)	0.0077 (2)
S1	0.0515 (8)	0.0395 (7)	0.0445 (7)	0.0213 (6)	−0.0044 (6)	0.0046 (5)
N1	0.060 (3)	0.049 (3)	0.057 (3)	0.025 (2)	−0.028 (3)	−0.012 (2)
N2	0.033 (2)	0.045 (3)	0.067 (3)	0.009 (2)	0.004 (2)	−0.008 (2)
O1	0.055 (3)	0.052 (3)	0.076 (3)	0.011 (2)	0.014 (2)	0.021 (2)
O2	0.036 (2)	0.075 (4)	0.124 (5)	0.009 (2)	−0.009 (3)	−0.004 (3)
C1	0.052 (3)	0.046 (3)	0.038 (3)	0.025 (2)	0.004 (2)	0.011 (2)
C2	0.057 (3)	0.046 (3)	0.031 (2)	0.030 (2)	−0.004 (2)	−0.001 (2)
C3	0.059 (3)	0.054 (3)	0.044 (3)	0.034 (3)	−0.001 (2)	−0.002 (2)
C4	0.066 (4)	0.060 (4)	0.050 (3)	0.037 (3)	0.014 (3)	−0.003 (3)
C5	0.073 (4)	0.048 (3)	0.044 (3)	0.020 (3)	0.015 (3)	−0.003 (2)
C6	0.052 (3)	0.045 (3)	0.044 (3)	0.013 (2)	0.006 (2)	0.006 (2)
C7	0.036 (2)	0.030 (2)	0.034 (2)	0.0157 (18)	0.0034 (18)	−0.0011 (17)
C8	0.032 (2)	0.033 (2)	0.041 (2)	0.0138 (18)	0.0014 (18)	−0.0049 (18)
C9	0.048 (3)	0.054 (3)	0.050 (3)	0.032 (3)	−0.008 (2)	−0.007 (2)
C10	0.076 (4)	0.056 (3)	0.044 (3)	0.041 (3)	−0.005 (3)	0.001 (3)
C11	0.060 (3)	0.042 (3)	0.040 (3)	0.020 (3)	0.009 (2)	0.009 (2)
C12	0.039 (2)	0.036 (2)	0.037 (2)	0.014 (2)	0.0032 (19)	−0.0011 (18)

I1—C1	2.092 (6)	C4—H4	0.93
S1—N1	1.696 (6)	C5—C6	1.352 (10)
S1—C7	1.781 (5)	C5—H5	0.93
N1—C2	1.441 (7)	C6—H6	0.93
N1—H1	0.86	C7—C12	1.390 (7)
N2—O1	1.216 (8)	C7—C8	1.399 (7)
N2—O2	1.219 (7)	C8—C9	1.392 (8)
N2—C8	1.458 (7)	C9—C10	1.365 (10)
C1—C6	1.391 (9)	C9—H9	0.93
C1—C2	1.402 (8)	C10—C11	1.386 (10)
C2—C3	1.392 (8)	C10—H10	0.93
C3—C4	1.375 (9)	C11—C12	1.387 (8)
C3—H3	0.93	C11—H11	0.93
C4—C5	1.400 (11)	C12—H12	0.93
N1—S1—C7	102.9 (3)	C5—C6—C1	120.3 (6)
C2—N1—S1	122.0 (5)	C5—C6—H6	119.8
C2—N1—H1	119	C1—C6—H6	119.8
S1—N1—H1	119	C12—C7—C8	116.5 (5)
O1—N2—O2	123.7 (6)	C12—C7—S1	120.5 (4)
O1—N2—C8	117.8 (5)	C8—C7—S1	122.9 (4)
O2—N2—C8	118.5 (6)	C9—C8—C7	121.8 (5)
C6—C1—C2	121.3 (6)	C9—C8—N2	118.4 (5)
C6—C1—I1	119.6 (5)	C7—C8—N2	119.7 (5)
C2—C1—I1	119.1 (4)	C10—C9—C8	120.5 (5)
C3—C2—C1	117.1 (5)	C10—C9—H9	119.8
C3—C2—N1	122.3 (5)	C8—C9—H9	119.8
C1—C2—N1	120.6 (5)	C9—C10—C11	118.8 (6)
C4—C3—C2	121.6 (6)	C9—C10—H10	120.6
C4—C3—H3	119.2	C11—C10—H10	120.6
C2—C3—H3	119.2	C10—C11—C12	120.8 (5)
C3—C4—C5	119.9 (6)	C10—C11—H11	119.6
C3—C4—H4	120.1	C12—C11—H11	119.6
C5—C4—H4	120.1	C11—C12—C7	121.5 (5)
C6—C5—C4	119.8 (6)	C11—C12—H12	119.3
C6—C5—H5	120.1	C7—C12—H12	119.3
C4—C5—H5	120.1
C7—S1—N1—C2	83.9 (5)	C12—C7—C8—C9	1.0 (7)
C6—C1—C2—C3	1.3 (8)	S1—C7—C8—C9	178.9 (4)
I1—C1—C2—C3	−179.0 (4)	C12—C7—C8—N2	180.0 (5)
C6—C1—C2—N1	−179.0 (5)	S1—C7—C8—N2	−2.1 (7)
I1—C1—C2—N1	0.8 (7)	O1—N2—C8—C9	170.0 (6)
S1—N1—C2—C3	−16.1 (8)	O2—N2—C8—C9	−8.4 (8)
S1—N1—C2—C1	164.2 (4)	O1—N2—C8—C7	−9.0 (8)
C1—C2—C3—C4	−0.2 (9)	O2—N2—C8—C7	172.6 (6)
N1—C2—C3—C4	−179.9 (6)	C7—C8—C9—C10	1.0 (9)
C2—C3—C4—C5	−1.2 (10)	N2—C8—C9—C10	−178.0 (5)
C3—C4—C5—C6	1.4 (10)	C8—C9—C10—C11	−2.5 (9)
C4—C5—C6—C1	−0.3 (9)	C9—C10—C11—C12	2.2 (9)
C2—C1—C6—C5	−1.0 (9)	C10—C11—C12—C7	−0.3 (9)
I1—C1—C6—C5	179.2 (5)	C8—C7—C12—C11	−1.3 (7)
N1—S1—C7—C12	1.6 (5)	S1—C7—C12—C11	−179.3 (4)
N1—S1—C7—C8	−176.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1i	0.93	2.55	3.445 (10)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1i	0.93	2.55	3.445 (10)	161

Symmetry code: (i) .