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

The title compound, C(9)H(9)ClN(2)O(5)S, is of inter-est as a precursor to biologically active substituted quinolines and related compounds. The structure displays inter-molecular C-H⋯O inter-actions. Each mol-ecule is linked to two adjacent neighbours via weak centrosymmetric dimer-forming inter-actions, forming chains in the [101] direction.

Related literature

For synthesis and biological evaluation of sulfur-containing heterocyclic compounds, see: Zia-ur-Rehman et al. (2005 ▶, 2006 ▶, 2007 ▶, 2008 ▶); Wen et al. (2005 ▶); Zhang, Xu, Wen et al. (2006 ▶). For related mol­ecules, see: (Wen et al., 2006 ▶; Zhang, Xu, Zou et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H9ClN2O5S

M = 292.70

Monoclinic,

a = 9.8071 (4) Å

b = 9.4310 (4) Å

c = 13.5679 (7) Å

β = 105.883 (2)°

V = 1207.00 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 296 (2) K

0.25 × 0.15 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.913, T max = 0.956

13383 measured reflections

2988 independent reflections

2077 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.02

2981 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032157/ez2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032157/ez2142Isup2.hkl

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

C9H9ClN2O5S	F(000) = 600
Mr = 292.70	Dx = 1.611 Mg m−3
Monoclinic, P21/c	Melting point: 401 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.8071 (4) Å	Cell parameters from 3121 reflections
b = 9.4310 (4) Å	θ = 2.7–27.2°
c = 13.5679 (7) Å	µ = 0.50 mm−1
β = 105.883 (2)°	T = 296 K
V = 1207.00 (9) Å3	Needle, light yellow
Z = 4	0.25 × 0.15 × 0.09 mm

Bruker APEXII CCD area-detector diffractometer	2988 independent reflections
Radiation source: fine-focus sealed tube	2077 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 7.5 pixels mm-1	θmax = 28.3°, θmin = 2.7°
φ and ω scans	h = −12→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.913, Tmax = 0.956	l = −18→17
13383 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0426P)2 + 0.5587P] where P = (Fo2 + 2Fc2)/3
2981 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.43 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	0.43935 (5)	0.98058 (6)	0.14520 (4)	0.03097 (15)
Cl1	−0.20712 (6)	0.67766 (7)	−0.00125 (6)	0.0511 (2)
N2	0.34896 (17)	0.91810 (19)	0.22582 (14)	0.0276 (4)
O5	0.34507 (18)	0.96150 (18)	0.04574 (13)	0.0439 (4)
C4	0.2107 (2)	0.8605 (2)	0.17969 (16)	0.0269 (5)
O3	0.52800 (17)	0.97095 (19)	0.36537 (13)	0.0454 (4)
N1	0.0872 (2)	1.0934 (2)	0.18329 (16)	0.0361 (5)
C3	0.0874 (2)	0.9425 (2)	0.15362 (17)	0.0283 (5)
O1	−0.0130 (2)	1.1651 (2)	0.13957 (18)	0.0695 (7)
C1	−0.0476 (2)	0.7464 (3)	0.07164 (19)	0.0365 (5)
O4	0.49004 (18)	1.11878 (17)	0.17659 (15)	0.0477 (5)
O2	0.1842 (2)	1.1381 (2)	0.25205 (18)	0.0651 (6)
C5	0.1996 (2)	0.7188 (2)	0.15196 (19)	0.0359 (5)
H5	0.2800	0.6618	0.1689	0.043*
C6	0.0708 (2)	0.6607 (3)	0.09955 (19)	0.0401 (6)
H6	0.0639	0.5647	0.0833	0.048*
C7	0.4104 (2)	0.9221 (2)	0.33238 (17)	0.0315 (5)
C2	−0.0409 (2)	0.8874 (2)	0.09933 (18)	0.0327 (5)
H2	−0.1215	0.9441	0.0816	0.039*
C8	0.5815 (3)	0.8637 (3)	0.1615 (2)	0.0501 (7)
H8A	0.5463	0.7690	0.1460	0.075*
H8B	0.6390	0.8679	0.2312	0.075*
H8C	0.6374	0.8899	0.1163	0.075*
C9	0.3259 (3)	0.8606 (3)	0.39765 (19)	0.0415 (6)
H9A	0.2285	0.8887	0.3716	0.062*
H9B	0.3621	0.8944	0.4666	0.062*
H9C	0.3323	0.7591	0.3969	0.062*

	U11	U22	U33	U12	U13	U23
S1	0.0248 (3)	0.0320 (3)	0.0347 (3)	0.0000 (2)	0.0057 (2)	0.0040 (2)
Cl1	0.0311 (3)	0.0557 (4)	0.0567 (4)	−0.0129 (3)	−0.0043 (3)	−0.0082 (3)
N2	0.0209 (8)	0.0327 (9)	0.0269 (10)	−0.0027 (7)	0.0024 (7)	−0.0027 (8)
O5	0.0386 (9)	0.0575 (11)	0.0322 (10)	−0.0048 (8)	0.0039 (8)	0.0063 (8)
C4	0.0208 (9)	0.0328 (11)	0.0253 (11)	−0.0021 (8)	0.0032 (8)	−0.0017 (9)
O3	0.0317 (9)	0.0564 (11)	0.0388 (10)	−0.0073 (8)	−0.0064 (8)	−0.0053 (8)
N1	0.0334 (10)	0.0337 (10)	0.0424 (12)	0.0039 (8)	0.0123 (9)	−0.0019 (9)
C3	0.0268 (10)	0.0283 (11)	0.0292 (12)	−0.0009 (8)	0.0066 (9)	−0.0012 (9)
O1	0.0571 (13)	0.0447 (11)	0.0897 (17)	0.0213 (10)	−0.0088 (12)	−0.0094 (11)
C1	0.0256 (11)	0.0426 (13)	0.0364 (14)	−0.0069 (10)	0.0002 (10)	−0.0021 (10)
O4	0.0457 (10)	0.0354 (9)	0.0607 (13)	−0.0111 (8)	0.0124 (9)	0.0025 (8)
O2	0.0447 (11)	0.0471 (11)	0.0889 (17)	0.0022 (9)	−0.0063 (11)	−0.0287 (11)
C5	0.0277 (11)	0.0326 (11)	0.0422 (15)	0.0037 (9)	0.0010 (10)	−0.0035 (10)
C6	0.0368 (13)	0.0329 (12)	0.0447 (15)	−0.0034 (10)	0.0012 (11)	−0.0067 (11)
C7	0.0308 (11)	0.0307 (11)	0.0291 (13)	0.0039 (9)	0.0016 (10)	−0.0025 (9)
C2	0.0202 (10)	0.0403 (12)	0.0356 (13)	0.0008 (9)	0.0043 (9)	0.0024 (10)
C8	0.0370 (14)	0.0579 (17)	0.0606 (19)	0.0155 (12)	0.0219 (13)	0.0118 (14)
C9	0.0489 (14)	0.0445 (14)	0.0309 (14)	0.0029 (11)	0.0104 (12)	0.0004 (11)

S1—O4	1.4182 (17)	C1—C2	1.379 (3)
S1—O5	1.4232 (18)	C1—C6	1.380 (3)
S1—N2	1.6913 (19)	C5—C6	1.382 (3)
S1—C8	1.743 (2)	C5—H5	0.9300
Cl1—C1	1.732 (2)	C6—H6	0.9300
N2—C7	1.406 (3)	C7—C9	1.487 (3)
N2—C4	1.435 (2)	C2—H2	0.9300
C4—C5	1.384 (3)	C8—H8A	0.9600
C4—C3	1.397 (3)	C8—H8B	0.9600
O3—C7	1.208 (3)	C8—H8C	0.9600
N1—O1	1.207 (2)	C9—H9A	0.9600
N1—O2	1.212 (3)	C9—H9B	0.9600
N1—C3	1.479 (3)	C9—H9C	0.9600
C3—C2	1.374 (3)
O4—S1—O5	118.97 (11)	C4—C5—H5	119.5
O4—S1—N2	109.18 (10)	C1—C6—C5	119.4 (2)
O5—S1—N2	104.46 (9)	C1—C6—H6	120.3
O4—S1—C8	109.91 (13)	C5—C6—H6	120.3
O5—S1—C8	109.27 (13)	O3—C7—N2	119.2 (2)
N2—S1—C8	103.88 (11)	O3—C7—C9	124.0 (2)
C7—N2—C4	123.11 (18)	N2—C7—C9	116.74 (19)
C7—N2—S1	120.17 (14)	C3—C2—C1	118.6 (2)
C4—N2—S1	116.71 (14)	C3—C2—H2	120.7
C5—C4—C3	117.84 (19)	C1—C2—H2	120.7
C5—C4—N2	118.61 (18)	S1—C8—H8A	109.5
C3—C4—N2	123.35 (18)	S1—C8—H8B	109.5
O1—N1—O2	123.1 (2)	H8A—C8—H8B	109.5
O1—N1—C3	117.83 (19)	S1—C8—H8C	109.5
O2—N1—C3	119.05 (19)	H8A—C8—H8C	109.5
C2—C3—C4	121.92 (19)	H8B—C8—H8C	109.5
C2—C3—N1	116.14 (18)	C7—C9—H9A	109.5
C4—C3—N1	121.95 (18)	C7—C9—H9B	109.5
C2—C1—C6	121.1 (2)	H9A—C9—H9B	109.5
C2—C1—Cl1	119.02 (18)	C7—C9—H9C	109.5
C6—C1—Cl1	119.86 (18)	H9A—C9—H9C	109.5
C6—C5—C4	121.1 (2)	H9B—C9—H9C	109.5
C6—C5—H5	119.5
O4—S1—N2—C7	−50.92 (18)	O1—N1—C3—C4	163.6 (2)
O5—S1—N2—C7	−179.19 (16)	O2—N1—C3—C4	−18.8 (3)
C8—S1—N2—C7	66.30 (19)	C3—C4—C5—C6	0.5 (4)
O4—S1—N2—C4	130.04 (16)	N2—C4—C5—C6	−174.5 (2)
O5—S1—N2—C4	1.77 (17)	C2—C1—C6—C5	−3.1 (4)
C8—S1—N2—C4	−112.74 (18)	Cl1—C1—C6—C5	175.8 (2)
C7—N2—C4—C5	−91.8 (3)	C4—C5—C6—C1	2.1 (4)
S1—N2—C4—C5	87.2 (2)	C4—N2—C7—O3	179.2 (2)
C7—N2—C4—C3	93.5 (3)	S1—N2—C7—O3	0.2 (3)
S1—N2—C4—C3	−87.5 (2)	C4—N2—C7—C9	1.0 (3)
C5—C4—C3—C2	−2.1 (3)	S1—N2—C7—C9	−178.00 (16)
N2—C4—C3—C2	172.6 (2)	C4—C3—C2—C1	1.2 (4)
C5—C4—C3—N1	177.6 (2)	N1—C3—C2—C1	−178.6 (2)
N2—C4—C3—N1	−7.7 (3)	C6—C1—C2—C3	1.5 (4)
O1—N1—C3—C2	−16.7 (3)	Cl1—C1—C2—C3	−177.41 (18)
O2—N1—C3—C2	160.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5i	0.93	2.55	3.404 (3)	153
C9—H9B···O3ii	0.96	2.58	3.521 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5i	0.93	2.55	3.404 (3)	153
C9—H9B⋯O3ii	0.96	2.58	3.521 (3)	169

Symmetry codes: (i) ; (ii) .