2-Methyl-5-nitro-benzene-sulfonamide.

In the title compound, C(7)H(8)N(2)O(4)S, the nitro group is twisted by 9.61 (2)° relative to the benzene ring. In the crystal, mol-ecules are linked by N-H⋯O and N-H⋯(O,O) hydrogen bonds between the amino and sulfonyl groups, forming layers parallel to (001).

Related literature

For the biological activity of sulfonamides, see: Ozbek et al. (2007 ▶); Parari et al. (2008 ▶); Ratish et al. (2009 ▶); Selnam et al. (2001 ▶). For related structures, see: Arshad et al. (2009 ▶); Gowda et al. (2007a ▶,b ▶,c ▶); Khan et al. (2009 ▶); Haider et al.(2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C7H8N2O4S

M = 216.21

Orthorhombic,

a = 4.9872 (4) Å

b = 6.2814 (5) Å

c = 28.557 (2) Å

V = 894.60 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.43 × 0.17 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.864, T max = 0.962

5964 measured reflections

2113 independent reflections

1549 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.099

S = 0.89

2112 reflections

136 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 766 Friedel pairs

Flack parameter: −0.02 (11)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053069/is2494sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053069/is2494Isup2.hkl

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

C7H8N2O4S	F(000) = 448
Mr = 216.21	Dx = 1.605 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1325 reflections
a = 4.9872 (4) Å	θ = 2.9–25.4°
b = 6.2814 (5) Å	µ = 0.35 mm−1
c = 28.557 (2) Å	T = 296 K
V = 894.60 (12) Å3	Needles, colourless
Z = 4	0.43 × 0.17 × 0.11 mm

Bruker APEXII CCD area-detector diffractometer	2113 independent reflections
Radiation source: fine-focus sealed tube	1549 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −3→6
Tmin = 0.864, Tmax = 0.962	k = −8→8
5964 measured reflections	l = −38→38

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.1986P] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max < 0.001
2112 reflections	Δρmax = 0.23 e Å−3
136 parameters	Δρmin = −0.23 e Å−3
0 restraints	Absolute structure: Flack (1983), 766 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (11)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.7436 (6)	0.4718 (4)	0.85981 (8)	0.0294 (6)
C2	0.6274 (6)	0.6621 (4)	0.87573 (9)	0.0336 (6)
C3	0.7125 (7)	0.7374 (4)	0.91916 (10)	0.0433 (8)
H3	0.6392	0.8629	0.9308	0.052*
C4	0.9018 (6)	0.6316 (5)	0.94542 (9)	0.0425 (7)
H4	0.9568	0.6857	0.9742	0.051*
C5	1.0083 (7)	0.4455 (4)	0.92867 (9)	0.0342 (6)
C6	0.9298 (6)	0.3616 (4)	0.88605 (8)	0.0330 (6)
H6	1.0009	0.2338	0.8753	0.040*
C7	0.4234 (7)	0.7867 (5)	0.84858 (11)	0.0473 (9)
H7A	0.3861	0.9178	0.8646	0.071*
H7B	0.2615	0.7051	0.8459	0.071*
H7C	0.4922	0.8171	0.8179	0.071*
N1	1.2116 (5)	0.3335 (4)	0.95582 (8)	0.0431 (6)
O4	0.3903 (4)	0.3752 (4)	0.79524 (7)	0.0525 (6)
O1	1.3007 (5)	0.4194 (3)	0.99090 (7)	0.0568 (6)
O2	1.2851 (5)	0.1593 (4)	0.94205 (8)	0.0677 (7)
O3	0.7986 (4)	0.1599 (3)	0.80208 (7)	0.0465 (5)
N3	0.8152 (8)	0.5117 (5)	0.76612 (9)	0.0532 (8)
S1	0.67301 (15)	0.36352 (11)	0.80358 (2)	0.03595 (19)
H1N	0.720 (8)	0.605 (5)	0.7540 (12)	0.062 (12)*
H2N	0.994 (12)	0.509 (7)	0.7660 (14)	0.091 (16)*

	U11	U22	U33	U12	U13	U23
C1	0.0257 (18)	0.0334 (12)	0.0292 (11)	−0.0031 (12)	0.0030 (11)	0.0005 (10)
C2	0.0294 (18)	0.0338 (13)	0.0374 (12)	−0.0008 (13)	0.0030 (11)	0.0044 (11)
C3	0.046 (2)	0.0403 (14)	0.0437 (15)	0.0085 (15)	0.0036 (15)	−0.0086 (12)
C4	0.047 (2)	0.0469 (15)	0.0334 (12)	0.0080 (17)	−0.0022 (13)	−0.0102 (13)
C5	0.0295 (18)	0.0429 (14)	0.0301 (12)	0.0029 (13)	0.0029 (12)	0.0031 (11)
C6	0.0313 (17)	0.0345 (12)	0.0333 (12)	0.0013 (14)	0.0065 (11)	−0.0029 (12)
C7	0.045 (2)	0.0428 (16)	0.0541 (17)	0.0074 (15)	0.0010 (16)	0.0078 (13)
N1	0.0377 (16)	0.0553 (14)	0.0362 (11)	0.0095 (15)	−0.0022 (11)	0.0052 (11)
O4	0.0291 (12)	0.0768 (14)	0.0515 (12)	−0.0103 (12)	−0.0018 (9)	−0.0106 (11)
O1	0.0521 (16)	0.0746 (15)	0.0436 (11)	0.0029 (13)	−0.0166 (11)	−0.0034 (10)
O2	0.0711 (19)	0.0721 (14)	0.0598 (14)	0.0387 (16)	−0.0127 (13)	−0.0080 (12)
O3	0.0495 (14)	0.0433 (10)	0.0467 (10)	−0.0050 (11)	0.0040 (10)	−0.0132 (9)
N3	0.039 (2)	0.079 (2)	0.0415 (13)	−0.0008 (19)	0.0032 (15)	0.0203 (14)
S1	0.0296 (4)	0.0473 (4)	0.0310 (3)	−0.0068 (4)	0.0021 (3)	−0.0038 (3)

C1—C6	1.379 (4)	C6—H6	0.9300
C1—C2	1.404 (4)	C7—H7A	0.9600
C1—S1	1.779 (3)	C7—H7B	0.9600
C2—C3	1.393 (4)	C7—H7C	0.9600
C2—C7	1.499 (4)	N1—O1	1.221 (3)
C3—C4	1.377 (4)	N1—O2	1.219 (3)
C3—H3	0.9300	O4—S1	1.432 (2)
C4—C5	1.370 (4)	O3—S1	1.425 (2)
C4—H4	0.9300	N3—S1	1.586 (3)
C5—C6	1.383 (3)	N3—H1N	0.83 (4)
C5—N1	1.457 (4)	N3—H2N	0.89 (6)
C6—C1—C2	122.0 (2)	C2—C7—H7A	109.5
C6—C1—S1	115.57 (19)	C2—C7—H7B	109.5
C2—C1—S1	122.4 (2)	H7A—C7—H7B	109.5
C3—C2—C1	116.8 (2)	C2—C7—H7C	109.5
C3—C2—C7	119.3 (3)	H7A—C7—H7C	109.5
C1—C2—C7	123.9 (2)	H7B—C7—H7C	109.5
C4—C3—C2	122.0 (3)	O1—N1—O2	123.5 (3)
C4—C3—H3	119.0	O1—N1—C5	118.5 (2)
C2—C3—H3	119.0	O2—N1—C5	118.1 (2)
C5—C4—C3	119.2 (3)	S1—N3—H1N	116 (3)
C5—C4—H4	120.4	S1—N3—H2N	116 (3)
C3—C4—H4	120.4	H1N—N3—H2N	126 (4)
C4—C5—C6	121.5 (3)	O3—S1—O4	118.28 (15)
C4—C5—N1	119.7 (2)	O3—S1—N3	108.08 (18)
C6—C5—N1	118.8 (2)	O4—S1—N3	107.33 (18)
C1—C6—C5	118.5 (2)	O3—S1—C1	106.47 (12)
C1—C6—H6	120.7	O4—S1—C1	108.99 (13)
C5—C6—H6	120.7	N3—S1—C1	107.21 (15)
C6—C1—C2—C3	1.2 (4)	N1—C5—C6—C1	−177.9 (2)
S1—C1—C2—C3	−175.9 (2)	C4—C5—N1—O1	−6.9 (4)
C6—C1—C2—C7	−179.7 (3)	C6—C5—N1—O1	172.3 (3)
S1—C1—C2—C7	3.3 (4)	C4—C5—N1—O2	173.7 (3)
C1—C2—C3—C4	0.1 (4)	C6—C5—N1—O2	−7.1 (4)
C7—C2—C3—C4	−179.1 (3)	C6—C1—S1—O3	9.8 (2)
C2—C3—C4—C5	−0.6 (5)	C2—C1—S1—O3	−173.0 (2)
C3—C4—C5—C6	0.0 (4)	C6—C1—S1—O4	138.5 (2)
C3—C4—C5—N1	179.2 (3)	C2—C1—S1—O4	−44.3 (3)
C2—C1—C6—C5	−1.8 (4)	C6—C1—S1—N3	−105.7 (2)
S1—C1—C6—C5	175.4 (2)	C2—C1—S1—N3	71.6 (3)
C4—C5—C6—C1	1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···O4i	0.83 (4)	2.27 (4)	3.055 (4)	158 (3)
N3—H2N···O4ii	0.89 (6)	2.30 (6)	3.107 (4)	150 (4)
N3—H2N···O3iii	0.89 (6)	2.40 (4)	2.893 (4)	115 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N⋯O4i	0.83 (4)	2.27 (4)	3.055 (4)	158 (3)
N3—H2N⋯O4ii	0.89 (6)	2.30 (6)	3.107 (4)	150 (4)
N3—H2N⋯O3iii	0.89 (6)	2.40 (4)	2.893 (4)	115 (3)

Symmetry codes: (i) ; (ii) ; (iii) .