2-(2-Nitro-phenyl-sulfin-yl)acetonitrile.

In the title compound, C8H6N2O3S, the dihedral angle between the nitro group and the benzene ring is 6.76 (9)°. The bond-angle sum at the S atom is 308.1°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds to generate (010) sheets. The crystal studied was found to be a racemic twin.

Related literature

For a related structure and background to sulfoxides, see: Benmebarek et al. (2012 ▶). For related structures see: Yan (2010 ▶); Kobayashi et al. (2003 ▶).

Experimental

Crystal data

C8H6N2O3S

M = 210.21

Orthorhombic,

a = 5.4114 (2) Å

b = 10.7602 (4) Å

c = 15.1837 (5) Å

V = 884.11 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 295 K

0.26 × 0.2 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

8401 measured reflections

2348 independent reflections

2222 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.070

S = 1.05

2348 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1379 Friedel pairs

Flack parameter: 0.53 (1)

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004832/hb7044sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004832/hb7044Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004832/hb7044Isup3.cml

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

C8H6N2O3S	F(000) = 432
Mr = 210.21	Dx = 1.579 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6191 reflections
a = 5.4114 (2) Å	θ = 2.7–29.1°
b = 10.7602 (4) Å	µ = 0.35 mm−1
c = 15.1837 (5) Å	T = 295 K
V = 884.11 (5) Å3	Block, colourless
Z = 4	0.26 × 0.2 × 0.15 mm

Bruker APEXII CCD diffractometer	2222 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.016
Graphite monochromator	θmax = 29.1°, θmin = 4.0°
φ and ω scans	h = −6→7
8401 measured reflections	k = −14→14
2348 independent reflections	l = −20→20

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)] = 0.027	H-atom parameters constrained
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0327P)2 + 0.2515P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2348 reflections	Δρmax = 0.21 e Å−3
128 parameters	Δρmin = −0.18 e Å−3
0 restraints	Absolute structure: Flack (1983), 1379 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.53 (1)

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
S2	0.53769 (6)	0.02767 (3)	0.15053 (2)	0.02770 (9)
O2	0.5137 (2)	−0.06613 (11)	0.22173 (7)	0.0395 (3)
O11	0.4219 (4)	0.16230 (15)	−0.12118 (8)	0.0678 (5)
O12	0.5834 (2)	0.17541 (11)	0.00821 (9)	0.0453 (3)
N1	0.4351 (3)	0.13166 (12)	−0.04412 (9)	0.0352 (3)
N8	−0.0001 (3)	0.12996 (17)	0.28063 (10)	0.0515 (4)
C1	0.2643 (3)	0.03718 (13)	−0.01153 (9)	0.0263 (3)
C2	0.2906 (2)	−0.01016 (12)	0.07377 (8)	0.0235 (2)
C3	0.1293 (3)	−0.10289 (13)	0.10054 (10)	0.0294 (3)
H3	0.1443	−0.137	0.1566	0.035*
C4	−0.0546 (3)	−0.14513 (14)	0.04407 (11)	0.0357 (3)
H4	−0.1622	−0.2071	0.0628	0.043*
C5	−0.0795 (3)	−0.09610 (15)	−0.03950 (11)	0.0376 (3)
H5	−0.2034	−0.125	−0.0767	0.045*
C6	0.0809 (3)	−0.00355 (14)	−0.06796 (9)	0.0343 (3)
H6	0.0651	0.0304	−0.124	0.041*
C7	0.4040 (3)	0.17220 (14)	0.19493 (11)	0.0341 (3)
H7A	0.5225	0.2113	0.234	0.041*
H7B	0.3711	0.2292	0.1468	0.041*
C8	0.1763 (3)	0.14879 (15)	0.24274 (10)	0.0330 (3)

	U11	U22	U33	U12	U13	U23
S2	0.02549 (15)	0.02869 (16)	0.02891 (16)	0.00442 (13)	−0.00081 (13)	−0.00137 (13)
C1	0.0308 (6)	0.0236 (6)	0.0246 (6)	0.0010 (5)	0.0058 (5)	0.0006 (5)
O2	0.0509 (7)	0.0360 (5)	0.0316 (5)	0.0073 (5)	−0.0070 (5)	0.0061 (4)
C3	0.0344 (7)	0.0242 (6)	0.0296 (7)	−0.0001 (5)	0.0047 (6)	0.0007 (5)
O12	0.0399 (7)	0.0423 (6)	0.0537 (7)	−0.0116 (5)	0.0041 (6)	0.0087 (5)
C5	0.0359 (8)	0.0373 (8)	0.0395 (8)	0.0008 (7)	−0.0071 (7)	−0.0108 (6)
N1	0.0417 (7)	0.0303 (6)	0.0336 (6)	−0.0008 (6)	0.0104 (6)	0.0055 (5)
N8	0.0469 (10)	0.0585 (9)	0.0492 (8)	0.0082 (8)	0.0136 (8)	−0.0025 (7)
C2	0.0249 (6)	0.0216 (6)	0.0241 (6)	0.0019 (5)	0.0024 (5)	−0.0019 (5)
C4	0.0326 (7)	0.0291 (6)	0.0453 (8)	−0.0061 (6)	0.0045 (7)	−0.0038 (6)
C6	0.0440 (8)	0.0347 (7)	0.0244 (6)	0.0065 (6)	−0.0034 (6)	−0.0033 (5)
O11	0.0987 (13)	0.0692 (10)	0.0354 (6)	−0.0252 (9)	0.0125 (8)	0.0169 (6)
C8	0.0360 (8)	0.0329 (7)	0.0299 (7)	0.0085 (6)	−0.0016 (6)	−0.0045 (6)
C7	0.0337 (8)	0.0286 (7)	0.0401 (8)	0.0006 (6)	0.0013 (6)	−0.0080 (6)

S2—O2	1.4846 (11)	C5—C4	1.381 (2)
S2—C2	1.8197 (13)	C5—C6	1.390 (2)
S2—C7	1.8429 (15)	C5—H5	0.93
C1—C6	1.382 (2)	N1—O11	1.2177 (17)
C1—C2	1.3989 (18)	N8—C8	1.133 (2)
C1—N1	1.4606 (18)	C4—H4	0.93
C3—C2	1.3867 (19)	C6—H6	0.93
C3—C4	1.390 (2)	C8—C7	1.452 (2)
C3—H3	0.93	C7—H7A	0.97
O12—N1	1.2235 (19)	C7—H7B	0.97
O2—S2—C2	104.49 (6)	C3—C2—S2	115.83 (10)
O2—S2—C7	105.84 (7)	C1—C2—S2	125.91 (10)
C2—S2—C7	97.74 (7)	C5—C4—C3	120.78 (15)
C6—C1—C2	122.12 (13)	C5—C4—H4	119.6
C6—C1—N1	117.72 (12)	C3—C4—H4	119.6
C2—C1—N1	120.16 (12)	C1—C6—C5	118.86 (13)
C2—C3—C4	120.35 (13)	C1—C6—H6	120.6
C2—C3—H3	119.8	C5—C6—H6	120.6
C4—C3—H3	119.8	N8—C8—C7	179.36 (19)
C4—C5—C6	119.90 (15)	C8—C7—S2	111.69 (11)
C4—C5—H5	120	C8—C7—H7A	109.3
C6—C5—H5	120	S2—C7—H7A	109.3
O11—N1—O12	123.94 (15)	C8—C7—H7B	109.3
O11—N1—C1	118.48 (15)	S2—C7—H7B	109.3
O12—N1—C1	117.58 (12)	H7A—C7—H7B	107.9
C3—C2—C1	117.97 (13)
C6—C1—N1—O11	−6.2 (2)	C7—S2—C2—C3	−102.58 (11)
C2—C1—N1—O11	173.11 (15)	O2—S2—C2—C1	−167.63 (11)
C6—C1—N1—O12	173.76 (14)	C7—S2—C2—C1	83.73 (12)
C2—C1—N1—O12	−7.0 (2)	C6—C5—C4—C3	0.1 (2)
C4—C3—C2—C1	−1.0 (2)	C2—C3—C4—C5	0.2 (2)
C4—C3—C2—S2	−175.24 (11)	C2—C1—C6—C5	−1.2 (2)
C6—C1—C2—C3	1.5 (2)	N1—C1—C6—C5	178.08 (13)
N1—C1—C2—C3	−177.73 (12)	C4—C5—C6—C1	0.3 (2)
C6—C1—C2—S2	175.08 (11)	O2—S2—C7—C8	−42.69 (13)
N1—C1—C2—S2	−4.16 (18)	C2—S2—C7—C8	64.82 (12)
O2—S2—C2—C3	6.06 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.93	2.41	3.3198 (18)	165
C7—H7A···O2ii	0.97	2.50	3.1190 (19)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.41	3.3198 (18)	165
C7—H7A⋯O2ii	0.97	2.50	3.1190 (19)	122

Symmetry codes: (i) ; (ii) .