N-Methyl-N-nitroso-p-toluene-sulfon-amide.

The crystal structure of the title compound, C8H10N2O3S, displays predominant C-H⋯O hydrogen-bonding and π-π stacking inter-actions. The hydrogen bonds are between the O atoms of the sulfonyl group and H atoms on methyl groups. The π-π stacking inter-actions occur between adjacent aromatic rings, with a centroid-centroid distance of 3.868 (11) Å. These inter-actions lead to the formation of chains parallel to (101).

Related literature

For the use of the title compound as a nitro­sylating agent, see: Mayer et al. (2014 ▶). For related structures, see: Hakkinen et al. (1988 ▶); Lightfoot et al. (1993 ▶). For the use of the title compound as a potential cancer chemotherapeutic, see: Garcia-Rio et al. (2011 ▶); Skinner et al. (1960 ▶). For its use as an anti­microbial, see: Uri & Scola (1992 ▶) and as a precursor in methyl­ene production and production of heterocyclic rings, see: Hudlicky (1980 ▶). For literature hydrogen-bond lengths between sulfonyl O atoms and methyl H atoms in sulfonamide structures, see: Dodoff et al. (2004 ▶). For the potential use of sulfonamide compounds as ligands for metal coordination, see: Jacobs et al. (2013 ▶).

Experimental

Crystal data

C8H10N2O3S

M = 214.24

Triclinic,

a = 6.8911 (8) Å

b = 8.4435 (10) Å

c = 8.6248 (10) Å

α = 81.458 (1)°

β = 85.883 (1)°

γ = 80.310 (1)°

V = 488.62 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.84 × 0.29 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2011 ▶) T min = 0.687, T max = 0.746

5753 measured reflections

2275 independent reflections

1892 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.09

2275 reflections

137 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (CrystalMaker, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814013518/fj2674sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013518/fj2674Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013518/fj2674Isup3.cml

CCDC reference: 1007700

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H10N2O3S	Z = 2
Mr = 214.24	F(000) = 224
Triclinic, P1	Dx = 1.456 Mg m−3
a = 6.8911 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4435 (10) Å	Cell parameters from 3237 reflections
c = 8.6248 (10) Å	θ = 2.5–28.1°
α = 81.458 (1)°	µ = 0.31 mm−1
β = 85.883 (1)°	T = 100 K
γ = 80.310 (1)°	Block, colorless
V = 488.62 (10) Å3	0.84 × 0.29 × 0.10 mm

Bruker APEXII CCD diffractometer	2275 independent reflections
Radiation source: fine-focus sealed tube	1892 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.3333 pixels mm-1	θmax = 28.4°, θmin = 2.4°
ω and φ scans	h = −9→9
Absorption correction: numerical (SADABS; Bruker, 2011)	k = −10→11
Tmin = 0.687, Tmax = 0.746	l = −11→11
5753 measured reflections

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)] = 0.037	Hydrogen site location: mixed
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.2042P] where P = (Fo2 + 2Fc2)/3
2275 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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
S1	0.20728 (6)	0.03322 (5)	0.28268 (5)	0.01794 (13)
O1	0.33666 (19)	−0.07228 (14)	0.38895 (14)	0.0234 (3)
O2	0.05198 (18)	−0.02289 (15)	0.21663 (15)	0.0239 (3)
O3	−0.1436 (2)	0.37946 (16)	0.40008 (15)	0.0301 (3)
N1	0.0960 (2)	0.18010 (17)	0.38888 (16)	0.0184 (3)
N2	−0.0760 (2)	0.26414 (19)	0.33146 (18)	0.0246 (3)
C1	0.3438 (2)	0.13715 (19)	0.13431 (19)	0.0167 (3)
C2	0.5359 (3)	0.1532 (2)	0.1589 (2)	0.0200 (4)
H2	0.5971	0.1025	0.2528	0.024*
C3	0.6369 (3)	0.2450 (2)	0.0434 (2)	0.0219 (4)
H3	0.7691	0.2557	0.0584	0.026*
C4	0.5484 (3)	0.3215 (2)	−0.0938 (2)	0.0204 (4)
C5	0.3552 (3)	0.3032 (2)	−0.1148 (2)	0.0220 (4)
H5	0.2932	0.3554	−0.2079	0.026*
C6	0.2519 (3)	0.2107 (2)	−0.0028 (2)	0.0204 (4)
H6	0.1209	0.1976	−0.0190	0.024*
C7	0.6590 (3)	0.4220 (2)	−0.2174 (2)	0.0282 (4)
H7A	0.7301	0.4901	−0.1669	0.042*
H7B	0.5657	0.4911	−0.2891	0.042*
H7C	0.7532	0.3502	−0.2764	0.042*
C8	0.1981 (3)	0.2380 (2)	0.5075 (2)	0.0219 (4)
H8A	0.194 (3)	0.352 (3)	0.480 (2)	0.033*
H8B	0.329 (3)	0.181 (3)	0.512 (2)	0.033*
H8C	0.137 (3)	0.215 (3)	0.609 (3)	0.033*

	U11	U22	U33	U12	U13	U23
S1	0.0207 (2)	0.0151 (2)	0.0183 (2)	−0.00448 (16)	0.00224 (16)	−0.00297 (15)
O1	0.0286 (7)	0.0165 (6)	0.0228 (6)	−0.0012 (5)	0.0013 (5)	0.0012 (5)
O2	0.0252 (7)	0.0247 (7)	0.0254 (7)	−0.0118 (5)	0.0032 (5)	−0.0084 (5)
O3	0.0338 (8)	0.0250 (7)	0.0277 (7)	0.0064 (6)	0.0014 (6)	−0.0053 (6)
N1	0.0195 (7)	0.0190 (7)	0.0165 (7)	−0.0018 (6)	0.0003 (6)	−0.0037 (6)
N2	0.0249 (8)	0.0241 (8)	0.0223 (8)	0.0016 (6)	−0.0004 (6)	−0.0019 (6)
C1	0.0203 (8)	0.0131 (8)	0.0170 (8)	−0.0030 (6)	0.0025 (6)	−0.0040 (6)
C2	0.0186 (8)	0.0207 (9)	0.0203 (8)	−0.0015 (7)	−0.0015 (7)	−0.0026 (7)
C3	0.0177 (9)	0.0226 (9)	0.0259 (9)	−0.0052 (7)	0.0016 (7)	−0.0039 (7)
C4	0.0274 (9)	0.0148 (8)	0.0192 (8)	−0.0039 (7)	0.0064 (7)	−0.0062 (7)
C5	0.0298 (10)	0.0199 (9)	0.0158 (8)	−0.0020 (7)	−0.0025 (7)	−0.0020 (7)
C6	0.0197 (9)	0.0226 (9)	0.0197 (9)	−0.0038 (7)	−0.0010 (7)	−0.0056 (7)
C7	0.0372 (11)	0.0228 (10)	0.0251 (10)	−0.0092 (8)	0.0092 (8)	−0.0046 (8)
C8	0.0269 (10)	0.0215 (9)	0.0187 (9)	−0.0063 (8)	−0.0008 (7)	−0.0046 (7)

S1—O2	1.4258 (13)	C3—H3	0.9500
S1—O1	1.4268 (13)	C4—C5	1.393 (3)
S1—N1	1.6975 (14)	C4—C7	1.506 (2)
S1—C1	1.7504 (17)	C5—C6	1.384 (2)
O3—N2	1.2224 (19)	C5—H5	0.9500
N1—N2	1.360 (2)	C6—H6	0.9500
N1—C8	1.466 (2)	C7—H7A	0.9800
C1—C2	1.388 (2)	C7—H7B	0.9800
C1—C6	1.394 (2)	C7—H7C	0.9800
C2—C3	1.390 (2)	C8—H8A	0.96 (2)
C2—H2	0.9500	C8—H8B	0.95 (2)
C3—C4	1.391 (2)	C8—H8C	0.96 (2)
O2—S1—O1	121.43 (8)	C3—C4—C7	120.73 (17)
O2—S1—N1	105.80 (7)	C5—C4—C7	120.63 (16)
O1—S1—N1	104.15 (7)	C6—C5—C4	121.35 (16)
O2—S1—C1	109.93 (8)	C6—C5—H5	119.3
O1—S1—C1	110.06 (8)	C4—C5—H5	119.3
N1—S1—C1	103.75 (7)	C5—C6—C1	118.66 (16)
N2—N1—C8	121.69 (14)	C5—C6—H6	120.7
N2—N1—S1	114.33 (11)	C1—C6—H6	120.7
C8—N1—S1	122.36 (12)	C4—C7—H7A	109.5
O3—N2—N1	113.28 (14)	C4—C7—H7B	109.5
C2—C1—C6	121.41 (16)	H7A—C7—H7B	109.5
C2—C1—S1	119.72 (13)	C4—C7—H7C	109.5
C6—C1—S1	118.76 (13)	H7A—C7—H7C	109.5
C1—C2—C3	118.62 (16)	H7B—C7—H7C	109.5
C1—C2—H2	120.7	N1—C8—H8A	108.3 (13)
C3—C2—H2	120.7	N1—C8—H8B	108.9 (13)
C2—C3—C4	121.31 (16)	H8A—C8—H8B	112.2 (19)
C2—C3—H3	119.3	N1—C8—H8C	110.6 (13)
C4—C3—H3	119.3	H8A—C8—H8C	110.3 (18)
C3—C4—C5	118.64 (16)	H8B—C8—H8C	106.5 (18)
O2—S1—N1—N2	−30.84 (14)	O1—S1—C1—C6	162.52 (13)
O1—S1—N1—N2	−159.92 (12)	N1—S1—C1—C6	−86.55 (14)
C1—S1—N1—N2	84.88 (13)	C6—C1—C2—C3	0.0 (2)
O2—S1—N1—C8	163.44 (13)	S1—C1—C2—C3	−175.94 (13)
O1—S1—N1—C8	34.37 (15)	C1—C2—C3—C4	0.8 (3)
C1—S1—N1—C8	−80.84 (15)	C2—C3—C4—C5	−0.6 (3)
C8—N1—N2—O3	−7.3 (2)	C2—C3—C4—C7	179.38 (16)
S1—N1—N2—O3	−173.13 (12)	C3—C4—C5—C6	−0.3 (3)
O2—S1—C1—C2	−157.71 (13)	C7—C4—C5—C6	179.71 (16)
O1—S1—C1—C2	−21.41 (16)	C4—C5—C6—C1	1.0 (3)
N1—S1—C1—C2	89.53 (14)	C2—C1—C6—C5	−0.9 (3)
O2—S1—C1—C6	26.22 (15)	S1—C1—C6—C5	175.10 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8b···O1i	0.95 (2)	2.49 (2)	3.401 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8b⋯O1i	0.95 (2)	2.49 (2)	3.401 (2)	160

Symmetry code: (i) .