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

In the title compound, C(10)H(12)N(2)O(6)S, the nitro group is twisted slightly out of the plane of the aromatic ring, forming a dihedral angle of 20.79 (1)°. In the crystal, the mol-ecules arrange themselves as a chain along the a axis through inter-molecular C-H⋯O inter-actions.

Related literature

For the synthesis of sulfur-containing heterocyclic compounds, see: Siddiqui et al. (2007 ▶); Wen et al. (2006 ▶); Zhang et al. (2006 ▶). For related structures, see: Zhang et al. (2006 ▶); Wen et al. (2005 ▶); Zia-ur-Rehman et al. (2008 ▶).

Experimental

Crystal data

C10H12N2O6S

M = 288.29

Monoclinic,

a = 7.1512 (2) Å

b = 15.4303 (5) Å

c = 11.3217 (3) Å

β = 91.769 (2)°

V = 1248.70 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.21 × 0.11 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.958, T max = 0.974

14122 measured reflections

3102 independent reflections

2101 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.128

S = 1.05

3102 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SMART (Bruker, 2007 ▶); data reduction: SAINT (Bruker, 2007 ▶); 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: SHELXTL (Sheldrick, 2008 ▶) and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011799/bt2918sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011799/bt2918Isup2.hkl

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

C10H12N2O6S	F(000) = 600
Mr = 288.29	Dx = 1.533 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3173 reflections
a = 7.1512 (2) Å	θ = 2.6–26.8°
b = 15.4303 (5) Å	µ = 0.28 mm−1
c = 11.3217 (3) Å	T = 296 K
β = 91.769 (2)°	Needles, yellow
V = 1248.70 (6) Å3	0.21 × 0.11 × 0.08 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3102 independent reflections
Radiation source: fine-focus sealed tube	2101 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→9
Tmin = 0.958, Tmax = 0.974	k = −20→20
14122 measured reflections	l = −15→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.2596P] where P = (Fo2 + 2Fc2)/3
3102 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.31 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	0.23442 (8)	0.16533 (4)	0.86323 (4)	0.03679 (18)
O1	0.3919 (3)	0.43383 (14)	0.73036 (15)	0.0788 (7)
O2	0.5342 (3)	0.31646 (11)	0.76949 (14)	0.0535 (5)
O3	0.0897 (2)	0.22746 (11)	0.84351 (15)	0.0493 (4)
O4	0.3188 (2)	0.12704 (11)	0.76361 (13)	0.0489 (4)
O5	0.1853 (2)	0.54616 (10)	1.10272 (14)	0.0473 (4)
O6	0.6008 (3)	0.10620 (12)	0.94545 (17)	0.0634 (5)
N1	0.4337 (3)	0.37563 (12)	0.79726 (15)	0.0390 (4)
N2	0.3979 (2)	0.21872 (11)	0.94551 (14)	0.0353 (4)
C1	0.3511 (3)	0.30400 (13)	0.98604 (17)	0.0311 (4)
C2	0.3598 (3)	0.37840 (13)	0.91680 (16)	0.0296 (4)
C3	0.3029 (3)	0.45779 (13)	0.95680 (17)	0.0334 (5)
H3	0.3089	0.5064	0.9084	0.040*
C4	0.2359 (3)	0.46491 (14)	1.07076 (18)	0.0341 (5)
C5	0.2273 (3)	0.39268 (15)	1.14165 (18)	0.0413 (6)
H5	0.1845	0.3973	1.2181	0.050*
C6	0.2828 (3)	0.31336 (15)	1.09848 (18)	0.0393 (5)
H6	0.2740	0.2647	1.1464	0.047*
C7	0.1573 (4)	0.08423 (16)	0.9575 (2)	0.0538 (7)
H7A	0.2552	0.0425	0.9707	0.081*
H7B	0.0497	0.0561	0.9222	0.081*
H7C	0.1245	0.1095	1.0316	0.081*
C8	0.1068 (4)	0.55680 (17)	1.2166 (2)	0.0525 (7)
H8A	0.0775	0.6168	1.2288	0.079*
H8B	0.1955	0.5379	1.2766	0.079*
H8C	−0.0053	0.5228	1.2209	0.079*
C9	0.5736 (3)	0.18093 (16)	0.97108 (19)	0.0431 (6)
C10	0.7164 (4)	0.23869 (19)	1.0292 (2)	0.0590 (7)
H10A	0.6632	0.2951	1.0409	0.089*
H10B	0.8226	0.2436	0.9798	0.089*
H10C	0.7552	0.2146	1.1042	0.089*

	U11	U22	U33	U12	U13	U23
S1	0.0472 (4)	0.0292 (3)	0.0344 (3)	−0.0019 (2)	0.0066 (2)	−0.0012 (2)
O1	0.1238 (19)	0.0701 (14)	0.0443 (10)	0.0384 (13)	0.0293 (11)	0.0251 (10)
O2	0.0705 (12)	0.0439 (10)	0.0476 (9)	0.0051 (9)	0.0257 (8)	−0.0059 (8)
O3	0.0464 (10)	0.0414 (10)	0.0595 (10)	0.0024 (8)	−0.0069 (8)	−0.0045 (8)
O4	0.0640 (11)	0.0455 (10)	0.0378 (8)	−0.0032 (8)	0.0122 (7)	−0.0081 (7)
O5	0.0607 (11)	0.0338 (9)	0.0480 (9)	0.0058 (8)	0.0120 (8)	−0.0095 (7)
O6	0.0757 (14)	0.0435 (11)	0.0705 (12)	0.0253 (10)	−0.0037 (10)	−0.0059 (9)
N1	0.0486 (12)	0.0364 (11)	0.0324 (9)	−0.0029 (9)	0.0081 (8)	0.0001 (8)
N2	0.0418 (11)	0.0276 (10)	0.0367 (9)	0.0042 (8)	0.0042 (7)	−0.0011 (7)
C1	0.0328 (11)	0.0271 (11)	0.0335 (10)	0.0007 (9)	0.0034 (8)	−0.0016 (8)
C2	0.0292 (11)	0.0312 (11)	0.0285 (9)	−0.0022 (9)	0.0037 (7)	−0.0016 (8)
C3	0.0378 (12)	0.0283 (11)	0.0341 (10)	−0.0029 (9)	0.0017 (8)	0.0015 (8)
C4	0.0320 (12)	0.0313 (12)	0.0391 (11)	0.0008 (9)	0.0029 (8)	−0.0084 (9)
C5	0.0494 (14)	0.0428 (14)	0.0324 (10)	−0.0010 (11)	0.0126 (9)	−0.0037 (10)
C6	0.0499 (14)	0.0333 (12)	0.0353 (10)	0.0013 (10)	0.0103 (9)	0.0060 (9)
C7	0.0731 (18)	0.0406 (14)	0.0486 (13)	−0.0138 (13)	0.0156 (12)	0.0016 (11)
C8	0.0554 (16)	0.0489 (15)	0.0540 (14)	0.0012 (12)	0.0161 (12)	−0.0194 (12)
C9	0.0476 (14)	0.0426 (14)	0.0394 (11)	0.0143 (11)	0.0041 (10)	0.0010 (10)
C10	0.0478 (16)	0.0689 (19)	0.0597 (15)	0.0149 (14)	−0.0081 (12)	−0.0093 (14)

S1—O3	1.4234 (17)	C3—H3	0.9300
S1—O4	1.4239 (15)	C4—C5	1.376 (3)
S1—N2	1.6868 (19)	C5—C6	1.381 (3)
S1—C7	1.745 (2)	C5—H5	0.9300
O1—N1	1.207 (2)	C6—H6	0.9300
O2—N1	1.209 (2)	C7—H7A	0.9600
O5—C4	1.357 (2)	C7—H7B	0.9600
O5—C8	1.432 (3)	C7—H7C	0.9600
O6—C9	1.206 (3)	C8—H8A	0.9600
N1—C2	1.469 (2)	C8—H8B	0.9600
N2—C9	1.407 (3)	C8—H8C	0.9600
N2—C1	1.437 (3)	C9—C10	1.493 (3)
C1—C6	1.385 (3)	C10—H10A	0.9600
C1—C2	1.393 (3)	C10—H10B	0.9600
C2—C3	1.372 (3)	C10—H10C	0.9600
C3—C4	1.394 (3)
O3—S1—O4	118.63 (10)	C4—C5—H5	120.2
O3—S1—N2	104.23 (9)	C6—C5—H5	120.2
O4—S1—N2	109.67 (10)	C5—C6—C1	122.1 (2)
O3—S1—C7	109.68 (13)	C5—C6—H6	119.0
O4—S1—C7	109.68 (11)	C1—C6—H6	119.0
N2—S1—C7	103.83 (11)	S1—C7—H7A	109.5
C4—O5—C8	117.47 (18)	S1—C7—H7B	109.5
O2—N1—O1	122.44 (18)	H7A—C7—H7B	109.5
O2—N1—C2	119.68 (18)	S1—C7—H7C	109.5
O1—N1—C2	117.88 (18)	H7A—C7—H7C	109.5
C9—N2—C1	121.94 (18)	H7B—C7—H7C	109.5
C9—N2—S1	120.69 (15)	O5—C8—H8A	109.5
C1—N2—S1	117.36 (14)	O5—C8—H8B	109.5
C6—C1—C2	117.03 (19)	H8A—C8—H8B	109.5
C6—C1—N2	118.78 (18)	O5—C8—H8C	109.5
C2—C1—N2	124.09 (17)	H8A—C8—H8C	109.5
C3—C2—C1	122.09 (17)	H8B—C8—H8C	109.5
C3—C2—N1	116.68 (18)	O6—C9—N2	119.8 (2)
C1—C2—N1	121.22 (18)	O6—C9—C10	124.3 (2)
C2—C3—C4	119.31 (19)	N2—C9—C10	116.0 (2)
C2—C3—H3	120.3	C9—C10—H10A	109.5
C4—C3—H3	120.3	C9—C10—H10B	109.5
O5—C4—C5	125.15 (19)	H10A—C10—H10B	109.5
O5—C4—C3	114.93 (19)	C9—C10—H10C	109.5
C5—C4—C3	119.91 (19)	H10A—C10—H10C	109.5
C4—C5—C6	119.54 (19)	H10B—C10—H10C	109.5
O3—S1—N2—C9	−172.42 (16)	O1—N1—C2—C1	160.0 (2)
O4—S1—N2—C9	−44.42 (19)	C1—C2—C3—C4	0.7 (3)
C7—S1—N2—C9	72.73 (18)	N1—C2—C3—C4	−178.38 (18)
O3—S1—N2—C1	6.58 (17)	C8—O5—C4—C5	−3.8 (3)
O4—S1—N2—C1	134.58 (15)	C8—O5—C4—C3	177.00 (19)
C7—S1—N2—C1	−108.27 (16)	C2—C3—C4—O5	179.21 (19)
C9—N2—C1—C6	−85.2 (3)	C2—C3—C4—C5	−0.1 (3)
S1—N2—C1—C6	95.8 (2)	O5—C4—C5—C6	179.9 (2)
C9—N2—C1—C2	98.7 (2)	C3—C4—C5—C6	−0.9 (3)
S1—N2—C1—C2	−80.3 (2)	C4—C5—C6—C1	1.4 (4)
C6—C1—C2—C3	−0.3 (3)	C2—C1—C6—C5	−0.7 (3)
N2—C1—C2—C3	175.92 (19)	N2—C1—C6—C5	−177.2 (2)
C6—C1—C2—N1	178.73 (19)	C1—N2—C9—O6	172.7 (2)
N2—C1—C2—N1	−5.0 (3)	S1—N2—C9—O6	−8.3 (3)
O2—N1—C2—C3	158.5 (2)	C1—N2—C9—C10	−7.6 (3)
O1—N1—C2—C3	−21.0 (3)	S1—N2—C9—C10	171.38 (17)
O2—N1—C2—C1	−20.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O3i	0.96	2.50	3.453 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O3i	0.96	2.50	3.453 (3)	169

Symmetry code: (i) .