1-Methyl-sulfon-yl-4-nitro-benzene.

In the title compound, C(7)H(7)NO(4)S, the nitro group is twisted by 10.2 (5) ° out of the plane of the benzene ring. Inversion-related mol-ecules are linked by non-classical C-H⋯O hydrogen bonds into dimers featuring an R(2) (2)(10) motif.

Related literature

For the synthesis, see: Nobles & Thompson (1965 ▶). For the supra­molecular patterns of nitro­phenyl compounds, see Glidewell et al. (2002 ▶); Ma (2007 ▶).

Experimental

Crystal data

C7H7NO4S

M = 201.20

Monoclinic,

a = 6.3765 (13) Å

b = 8.0411 (16) Å

c = 16.426 (3) Å

β = 91.67 (3)°

V = 841.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 291 (2) K

0.21 × 0.19 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.926, T max = 0.942

7967 measured reflections

1933 independent reflections

1045 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.152

S = 1.11

1933 reflections

119 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.45 e Å−3

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808035861/ng2509sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035861/ng2509Isup2.hkl

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

C7H7NO4S	F000 = 416
Mr = 201.20	Dx = 1.587 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4509 reflections
a = 6.3765 (13) Å	θ = 3.2–27.5º
b = 8.0411 (16) Å	µ = 0.36 mm−1
c = 16.426 (3) Å	T = 291 (2) K
β = 91.67 (3)º	Block, yellow
V = 841.9 (3) Å3	0.21 × 0.19 × 0.16 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	1933 independent reflections
Radiation source: fine-focus sealed tube	1045 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
T = 291(2) K	θmax = 27.5º
ω scan	θmin = 3.2º
Absorption correction: Multi-scan(ABSCOR; Higashi, 1995)	h = −8→8
Tmin = 0.926, Tmax = 0.942	k = −10→9
7967 measured reflections	l = −21→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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0576P)2 + 0.5194P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
1933 reflections	Δρmax = 0.32 e Å−3
119 parameters	Δρmin = −0.45 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1	0.1240 (5)	0.8495 (4)	0.09033 (17)	0.0426 (7)
C2	−0.0744 (5)	0.7940 (5)	0.1076 (2)	0.0546 (9)
H1	−0.1268	0.8094	0.1593	0.066*
C3	−0.1953 (6)	0.7154 (4)	0.0478 (2)	0.0548 (9)
H2	−0.3297	0.6777	0.0584	0.066*
C4	−0.1117 (5)	0.6945 (4)	−0.02732 (18)	0.0444 (8)
C5	0.0841 (5)	0.7492 (4)	−0.04584 (19)	0.0523 (9)
H3	0.1355	0.7340	−0.0977	0.063*
C6	0.2042 (5)	0.8273 (4)	0.01402 (18)	0.0480 (8)
H4	0.3384	0.8648	0.0030	0.058*
C7	0.3546 (7)	0.7850 (5)	0.2321 (2)	0.0716 (12)
H5	0.4392	0.8278	0.2767	0.107*
H6	0.4342	0.7053	0.2024	0.107*
H7	0.2320	0.7323	0.2528	0.107*
N1	−0.2387 (6)	0.6099 (3)	−0.09136 (19)	0.0586 (8)
O1	0.4601 (4)	1.0152 (3)	0.13042 (15)	0.0703 (8)
O2	0.1478 (4)	1.0591 (3)	0.21070 (16)	0.0754 (8)
O3	−0.1539 (5)	0.5713 (4)	−0.15365 (18)	0.0873 (10)
O4	−0.4225 (5)	0.5820 (4)	−0.07856 (17)	0.0822 (9)
S1	0.27883 (14)	0.94820 (10)	0.16746 (5)	0.0497 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0461 (18)	0.0391 (16)	0.0423 (16)	0.0029 (13)	−0.0008 (13)	0.0050 (13)
C2	0.051 (2)	0.068 (2)	0.0453 (17)	−0.0034 (17)	0.0038 (15)	0.0008 (16)
C3	0.046 (2)	0.063 (2)	0.0553 (19)	−0.0115 (17)	−0.0019 (16)	0.0019 (17)
C4	0.0487 (19)	0.0360 (15)	0.0475 (17)	0.0011 (14)	−0.0129 (14)	0.0033 (14)
C5	0.055 (2)	0.061 (2)	0.0411 (16)	0.0026 (17)	−0.0005 (15)	−0.0022 (16)
C6	0.0415 (18)	0.0573 (19)	0.0452 (17)	−0.0024 (15)	−0.0016 (14)	0.0034 (15)
C7	0.096 (3)	0.065 (2)	0.053 (2)	−0.004 (2)	−0.025 (2)	0.0075 (18)
N1	0.074 (2)	0.0427 (15)	0.0574 (18)	−0.0008 (15)	−0.0218 (16)	0.0021 (14)
O1	0.0643 (17)	0.0840 (18)	0.0619 (14)	−0.0326 (14)	−0.0080 (12)	0.0045 (14)
O2	0.083 (2)	0.0676 (16)	0.0756 (17)	0.0135 (15)	−0.0062 (14)	−0.0285 (14)
O3	0.104 (2)	0.086 (2)	0.0707 (18)	−0.0009 (17)	−0.0156 (17)	−0.0348 (16)
O4	0.073 (2)	0.093 (2)	0.0790 (18)	−0.0289 (16)	−0.0244 (15)	0.0059 (16)
S1	0.0566 (6)	0.0457 (5)	0.0461 (5)	−0.0040 (4)	−0.0074 (4)	−0.0011 (4)

C1—C2	1.378 (5)	C5—H3	0.9300
C1—C6	1.379 (4)	C6—H4	0.9300
C1—S1	1.771 (3)	C7—S1	1.747 (4)
C2—C3	1.384 (5)	C7—H5	0.9600
C2—H1	0.9300	C7—H6	0.9600
C3—C4	1.369 (5)	C7—H7	0.9600
C3—H2	0.9300	N1—O3	1.212 (4)
C4—C5	1.367 (5)	N1—O4	1.218 (4)
C4—N1	1.475 (4)	O1—S1	1.427 (3)
C5—C6	1.380 (4)	O2—S1	1.425 (3)
C2—C1—C6	120.8 (3)	C5—C6—H4	120.2
C2—C1—S1	119.6 (2)	S1—C7—H5	109.5
C6—C1—S1	119.6 (2)	S1—C7—H6	109.5
C1—C2—C3	119.8 (3)	H5—C7—H6	109.5
C1—C2—H1	120.1	S1—C7—H7	109.5
C3—C2—H1	120.1	H5—C7—H7	109.5
C4—C3—C2	118.2 (3)	H6—C7—H7	109.5
C4—C3—H2	120.9	O3—N1—O4	123.6 (3)
C2—C3—H2	120.9	O3—N1—C4	118.1 (3)
C5—C4—C3	122.9 (3)	O4—N1—C4	118.2 (3)
C5—C4—N1	118.4 (3)	O2—S1—O1	118.03 (18)
C3—C4—N1	118.6 (3)	O2—S1—C7	108.81 (19)
C4—C5—C6	118.6 (3)	O1—S1—C7	109.2 (2)
C4—C5—H3	120.7	O2—S1—C1	108.31 (16)
C6—C5—H3	120.7	O1—S1—C1	107.79 (15)
C1—C6—C5	119.6 (3)	C7—S1—C1	103.70 (16)
C1—C6—H4	120.2

D—H···A	D—H	H···A	D···A	D—H···A
C3—H2···O4i	0.93	2.65	3.462 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H2⋯O4i	0.93	2.65	3.462 (5)	147

Symmetry code: (i) .