N-(4-Meth-oxy-2-nitro-phen-yl)-N-(methyl-sulfon-yl)methane-sulfonamide.

In the title compound, C(9)H(12)N(2)O(7)S(2), the nitro substituent is slightly twisted from the benzene ring [dihedral angle = 14.69 (10)°]. The mol-ecular geometry is stabilized by intra-molecular C-H⋯O hydrogen bonds, forming S(6) ring motifs. In the crystal, molecules are linked by C-H⋯O hydrogen bonds into layers parallel to (10-2).

Related literature

For the biological activities of sulfonamides, see: Alsughayer et al. (2011 ▶); Joshi & Khosla (2003 ▶); Scozzafava et al. (2003 ▶); Drews (2000 ▶); Peixoto & Beverley (1987 ▶). For crystal structures of closely related compounds, see: Boechat et al. (2010 ▶); Zia-ur-Rehman et al. (2009 ▶).

Experimental

Crystal data

C9H12N2O7S2

M = 324.33

Monoclinic,

a = 9.4976 (7) Å

b = 7.5987 (6) Å

c = 19.2434 (15) Å

β = 103.672 (2)°

V = 1349.43 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 273 K

0.55 × 0.47 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.799, T max = 0.955

9504 measured reflections

3362 independent reflections

2711 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.05

3362 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202483X/is5148sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202483X/is5148Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202483X/is5148Isup3.cml

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

C9H12N2O7S2	F(000) = 672
Mr = 324.33	Dx = 1.596 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3096 reflections
a = 9.4976 (7) Å	θ = 2.2–27.7°
b = 7.5987 (6) Å	µ = 0.43 mm−1
c = 19.2434 (15) Å	T = 273 K
β = 103.672 (2)°	Block, yellow
V = 1349.43 (18) Å3	0.55 × 0.47 × 0.11 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3362 independent reflections
Radiation source: fine-focus sealed tube	2711 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scan	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
Tmin = 0.799, Tmax = 0.955	k = −10→9
9504 measured reflections	l = −25→23

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0641P)2 + 0.2074P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3362 reflections	Δρmax = 0.31 e Å−3
185 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0101 (14)

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	0.80706 (5)	0.21065 (6)	−0.02024 (2)	0.03866 (15)
S2	0.67671 (5)	0.31016 (6)	0.09782 (2)	0.03825 (15)
O1	0.55361 (15)	0.22596 (19)	0.05410 (8)	0.0529 (4)
O2	0.71498 (16)	0.2788 (2)	0.17294 (7)	0.0514 (4)
O3	0.95185 (15)	0.2109 (2)	−0.02879 (7)	0.0522 (4)
O4	0.70649 (16)	0.3355 (2)	−0.05856 (7)	0.0561 (4)
O5	0.80101 (17)	−0.07491 (19)	0.12618 (9)	0.0608 (4)
O6	0.99411 (19)	−0.20742 (17)	0.18046 (9)	0.0602 (4)
O7	1.36416 (14)	0.2232 (2)	0.25913 (8)	0.0503 (4)
N1	0.92993 (18)	−0.07629 (18)	0.15472 (8)	0.0381 (3)
N2	0.82155 (15)	0.24662 (18)	0.06736 (7)	0.0329 (3)
C1	1.14724 (19)	0.0885 (2)	0.20463 (9)	0.0345 (4)
H1B	1.1802	−0.0117	0.2313	0.041*
C2	1.01332 (18)	0.0890 (2)	0.15816 (8)	0.0311 (3)
C3	0.96028 (17)	0.2371 (2)	0.11724 (8)	0.0315 (3)
C4	1.04925 (19)	0.3835 (2)	0.12521 (10)	0.0406 (4)
H4B	1.0171	0.4833	0.0982	0.049*
C5	1.1838 (2)	0.3863 (2)	0.17185 (10)	0.0428 (4)
H5A	1.2407	0.4872	0.1764	0.051*
C6	1.23354 (19)	0.2382 (3)	0.21179 (9)	0.0366 (4)
C7	1.4561 (2)	0.3748 (3)	0.27101 (13)	0.0630 (6)
H7A	1.5458	0.3458	0.3040	0.095*
H7B	1.4090	0.4680	0.2905	0.095*
H7C	1.4752	0.4123	0.2265	0.095*
C8	0.6647 (3)	0.5369 (3)	0.08270 (13)	0.0576 (6)
H8A	0.5830	0.5830	0.0981	0.086*
H8B	0.6528	0.5598	0.0326	0.086*
H8C	0.7517	0.5927	0.1091	0.086*
C9	0.7335 (2)	−0.0003 (3)	−0.03754 (11)	0.0507 (5)
H9A	0.7196	−0.0262	−0.0875	0.076*
H9B	0.6421	−0.0054	−0.0246	0.076*
H9C	0.7986	−0.0849	−0.0100	0.076*

	U11	U22	U33	U12	U13	U23
S1	0.0379 (3)	0.0453 (3)	0.0321 (2)	−0.00244 (18)	0.00691 (18)	0.00241 (17)
S2	0.0339 (2)	0.0363 (2)	0.0449 (3)	−0.00356 (16)	0.00994 (18)	−0.00732 (18)
O1	0.0338 (7)	0.0560 (9)	0.0673 (10)	−0.0104 (6)	0.0088 (6)	−0.0157 (7)
O2	0.0573 (9)	0.0568 (9)	0.0437 (8)	−0.0021 (7)	0.0191 (6)	−0.0065 (6)
O3	0.0448 (8)	0.0697 (10)	0.0460 (8)	−0.0059 (7)	0.0185 (6)	−0.0001 (7)
O4	0.0582 (9)	0.0632 (9)	0.0421 (7)	0.0097 (7)	0.0020 (6)	0.0133 (7)
O5	0.0512 (9)	0.0431 (8)	0.0834 (11)	−0.0183 (7)	0.0065 (8)	0.0071 (7)
O6	0.0801 (12)	0.0310 (7)	0.0648 (10)	−0.0038 (7)	0.0078 (8)	0.0130 (7)
O7	0.0351 (7)	0.0564 (9)	0.0529 (8)	−0.0008 (6)	−0.0029 (6)	−0.0013 (7)
N1	0.0530 (9)	0.0287 (7)	0.0343 (7)	−0.0084 (6)	0.0137 (6)	−0.0001 (6)
N2	0.0306 (7)	0.0356 (7)	0.0310 (7)	−0.0017 (6)	0.0044 (5)	−0.0005 (6)
C1	0.0407 (9)	0.0316 (8)	0.0311 (8)	0.0033 (7)	0.0082 (6)	0.0031 (6)
C2	0.0388 (9)	0.0254 (8)	0.0307 (8)	−0.0054 (6)	0.0114 (6)	−0.0010 (6)
C3	0.0323 (8)	0.0300 (8)	0.0317 (8)	−0.0036 (6)	0.0062 (6)	0.0016 (6)
C4	0.0416 (10)	0.0297 (8)	0.0466 (10)	−0.0064 (7)	0.0029 (7)	0.0078 (7)
C5	0.0403 (10)	0.0347 (9)	0.0508 (11)	−0.0112 (7)	0.0054 (8)	0.0039 (8)
C6	0.0336 (9)	0.0417 (9)	0.0337 (9)	−0.0008 (7)	0.0065 (7)	−0.0032 (7)
C7	0.0358 (11)	0.0725 (15)	0.0743 (15)	−0.0108 (10)	0.0002 (10)	−0.0152 (13)
C8	0.0612 (14)	0.0352 (10)	0.0733 (15)	0.0068 (9)	0.0096 (11)	−0.0051 (10)
C9	0.0521 (12)	0.0529 (12)	0.0456 (11)	−0.0100 (9)	0.0089 (9)	−0.0160 (9)

S1—O4	1.4223 (15)	C1—H1B	0.9300
S1—O3	1.4231 (14)	C2—C3	1.397 (2)
S1—N2	1.6809 (14)	C3—C4	1.383 (2)
S1—C9	1.748 (2)	C4—C5	1.377 (2)
S2—O1	1.4210 (14)	C4—H4B	0.9300
S2—O2	1.4247 (14)	C5—C6	1.382 (3)
S2—N2	1.6882 (15)	C5—H5A	0.9300
S2—C8	1.747 (2)	C7—H7A	0.9600
O5—N1	1.218 (2)	C7—H7B	0.9600
O6—N1	1.211 (2)	C7—H7C	0.9600
O7—C6	1.359 (2)	C8—H8A	0.9600
O7—C7	1.431 (3)	C8—H8B	0.9600
N1—C2	1.478 (2)	C8—H8C	0.9600
N2—C3	1.437 (2)	C9—H9A	0.9600
C1—C2	1.371 (2)	C9—H9B	0.9600
C1—C6	1.389 (2)	C9—H9C	0.9600
O4—S1—O3	119.21 (9)	C5—C4—C3	122.23 (16)
O4—S1—N2	107.30 (8)	C5—C4—H4B	118.9
O3—S1—N2	105.27 (8)	C3—C4—H4B	118.9
O4—S1—C9	108.87 (10)	C4—C5—C6	119.50 (17)
O3—S1—C9	109.43 (10)	C4—C5—H5A	120.3
N2—S1—C9	105.93 (9)	C6—C5—H5A	120.3
O1—S2—O2	120.15 (9)	O7—C6—C5	125.38 (17)
O1—S2—N2	106.83 (8)	O7—C6—C1	114.93 (17)
O2—S2—N2	105.73 (8)	C5—C6—C1	119.70 (16)
O1—S2—C8	109.48 (11)	O7—C7—H7A	109.5
O2—S2—C8	108.96 (10)	O7—C7—H7B	109.5
N2—S2—C8	104.52 (10)	H7A—C7—H7B	109.5
C6—O7—C7	117.75 (16)	O7—C7—H7C	109.5
O6—N1—O5	123.14 (15)	H7A—C7—H7C	109.5
O6—N1—C2	117.92 (15)	H7B—C7—H7C	109.5
O5—N1—C2	118.94 (14)	S2—C8—H8A	109.5
C3—N2—S1	120.43 (11)	S2—C8—H8B	109.5
C3—N2—S2	118.43 (11)	H8A—C8—H8B	109.5
S1—N2—S2	120.96 (8)	S2—C8—H8C	109.5
C2—C1—C6	119.80 (16)	H8A—C8—H8C	109.5
C2—C1—H1B	120.1	H8B—C8—H8C	109.5
C6—C1—H1B	120.1	S1—C9—H9A	109.5
C1—C2—C3	121.66 (15)	S1—C9—H9B	109.5
C1—C2—N1	115.57 (14)	H9A—C9—H9B	109.5
C3—C2—N1	122.77 (15)	S1—C9—H9C	109.5
C4—C3—C2	117.11 (15)	H9A—C9—H9C	109.5
C4—C3—N2	118.25 (15)	H9B—C9—H9C	109.5
C2—C3—N2	124.63 (15)
O4—S1—N2—C3	−139.57 (14)	C1—C2—C3—C4	0.4 (2)
O3—S1—N2—C3	−11.63 (15)	N1—C2—C3—C4	−179.79 (15)
C9—S1—N2—C3	104.25 (14)	C1—C2—C3—N2	179.70 (15)
O4—S1—N2—S2	35.55 (12)	N1—C2—C3—N2	−0.5 (3)
O3—S1—N2—S2	163.50 (10)	S1—N2—C3—C4	82.83 (19)
C9—S1—N2—S2	−80.63 (12)	S2—N2—C3—C4	−92.42 (17)
O1—S2—N2—C3	−150.32 (13)	S1—N2—C3—C2	−96.42 (17)
O2—S2—N2—C3	−21.24 (15)	S2—N2—C3—C2	88.33 (19)
C8—S2—N2—C3	93.69 (15)	C2—C3—C4—C5	−0.8 (3)
O1—S2—N2—S1	34.46 (12)	N2—C3—C4—C5	179.87 (17)
O2—S2—N2—S1	163.53 (10)	C3—C4—C5—C6	0.7 (3)
C8—S2—N2—S1	−81.53 (12)	C7—O7—C6—C5	2.6 (3)
C6—C1—C2—C3	0.0 (3)	C7—O7—C6—C1	−177.73 (17)
C6—C1—C2—N1	−179.76 (15)	C4—C5—C6—O7	179.46 (18)
O6—N1—C2—C1	−14.8 (2)	C4—C5—C6—C1	−0.2 (3)
O5—N1—C2—C1	165.47 (17)	C2—C1—C6—O7	−179.86 (15)
O6—N1—C2—C3	165.42 (17)	C2—C1—C6—C5	−0.2 (3)
O5—N1—C2—C3	−14.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2i	0.93	2.46	3.368 (2)	165
C8—H8B···O4	0.96	2.58	3.225 (3)	125
C8—H8C···O5ii	0.96	2.58	3.250 (3)	127
C9—H9B···O1	0.96	2.59	3.226 (3)	124
C9—H9B···O1iii	0.96	2.47	3.173 (3)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O2i	0.93	2.46	3.368 (2)	165
C8—H8B⋯O4	0.96	2.58	3.225 (3)	125
C8—H8C⋯O5ii	0.96	2.58	3.250 (3)	127
C9—H9B⋯O1	0.96	2.59	3.226 (3)	124
C9—H9B⋯O1iii	0.96	2.47	3.173 (3)	130

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