2,2-Dichloro-N-(4-methyl-phenyl-sulfonyl)acetamide.

The N-H and C=O bonds in the title compound, C(9)H(9)Cl(2)NO(3)S, are trans to each other, similar to what is observed in 2,2,2-trimethyl-N-(phenyl-sulfon-yl)acetamide and 2,2,2-trimethyl-N-(4-methyl-phenyl-sulfon-yl)acetamide. The bond parameters in the title compound are also similar to those in the aforementioned two structures. N-H⋯O hydrogen bonds connect the mol-ecules into chains running along the a axis.

Related literature

For related literature, see: Gowda et al. (2006 ▶, 2007 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

C9H9Cl2NO3S

M = 282.13

Orthorhombic,

a = 9.6580 (8) Å

b = 10.3177 (8) Å

c = 23.067 (2) Å

V = 2298.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.74 mm−1

T = 299 (2) K

0.48 × 0.46 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.719, T max = 0.799

8079 measured reflections

2313 independent reflections

1886 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.099

S = 1.14

2313 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802134X/bt2744sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802134X/bt2744Isup2.hkl

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

C9H9Cl2NO3S	F000 = 1152
Mr = 282.13	Dx = 1.631 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3825 reflections
a = 9.6580 (8) Å	θ = 2.3–28.0º
b = 10.3177 (8) Å	µ = 0.74 mm−1
c = 23.067 (2) Å	T = 299 (2) K
V = 2298.6 (3) Å3	Prism, colourless
Z = 8	0.48 × 0.46 × 0.32 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2313 independent reflections
Radiation source: fine-focus sealed tube	1886 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 3.9º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −12→11
Tmin = 0.719, Tmax = 0.799	k = −12→11
8079 measured reflections	l = −28→28

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0465P)2 + 1.5357P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max = 0.001
S = 1.14	Δρmax = 0.34 e Å−3
2313 reflections	Δρmin = −0.33 e Å−3
150 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0216 (12)
Secondary atom site location: difference Fourier map

Experimental. CrysAlis RED (Oxford Diffraction, 2007) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.1940 (2)	0.2089 (2)	0.10903 (9)	0.0321 (5)
C2	0.3304 (3)	0.2325 (3)	0.09411 (11)	0.0419 (6)
H2	0.4022	0.1916	0.1138	0.050*
C3	0.3581 (3)	0.3181 (3)	0.04945 (11)	0.0487 (6)
H3	0.4497	0.3348	0.0395	0.058*
C4	0.2532 (3)	0.3796 (2)	0.01912 (10)	0.0440 (6)
C5	0.1181 (3)	0.3514 (3)	0.03428 (12)	0.0480 (6)
H5	0.0463	0.3897	0.0136	0.058*
C6	0.0866 (3)	0.2678 (2)	0.07928 (11)	0.0403 (6)
H6	−0.0050	0.2515	0.0893	0.048*
C7	0.2763 (2)	0.27000 (19)	0.24611 (9)	0.0279 (4)
C8	0.2502 (2)	0.3642 (2)	0.29677 (9)	0.0331 (5)
H8	0.1773	0.4255	0.2859	0.040*
C9	0.2837 (4)	0.4760 (3)	−0.02853 (13)	0.0626 (8)
H9A	0.3703	0.4545	−0.0466	0.075*
H9B	0.2892	0.5616	−0.0124	0.075*
H9C	0.2111	0.4731	−0.0569	0.075*
N1	0.15881 (18)	0.21543 (18)	0.22498 (8)	0.0292 (4)
H1N	0.084 (3)	0.238 (2)	0.2380 (11)	0.035*
O1	0.01360 (18)	0.07170 (18)	0.16642 (7)	0.0438 (4)
O2	0.26226 (19)	0.01713 (16)	0.17765 (7)	0.0433 (4)
O3	0.39079 (15)	0.24827 (17)	0.22726 (7)	0.0385 (4)
Cl1	0.40283 (7)	0.45024 (6)	0.31278 (3)	0.0454 (2)
Cl2	0.19595 (7)	0.27418 (7)	0.35847 (3)	0.0508 (2)
S1	0.15508 (6)	0.11055 (5)	0.16929 (2)	0.03130 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0352 (11)	0.0326 (11)	0.0285 (10)	−0.0022 (9)	−0.0002 (8)	−0.0039 (9)
C2	0.0335 (12)	0.0556 (16)	0.0366 (12)	−0.0025 (11)	0.0009 (10)	0.0018 (11)
C3	0.0431 (14)	0.0605 (17)	0.0424 (13)	−0.0122 (12)	0.0083 (11)	0.0013 (13)
C4	0.0633 (16)	0.0372 (13)	0.0315 (11)	−0.0068 (11)	0.0046 (11)	−0.0024 (10)
C5	0.0556 (16)	0.0421 (14)	0.0463 (14)	0.0060 (12)	−0.0039 (12)	0.0077 (12)
C6	0.0353 (12)	0.0431 (14)	0.0424 (13)	0.0005 (10)	−0.0013 (10)	0.0029 (11)
C7	0.0282 (11)	0.0269 (10)	0.0285 (10)	0.0026 (8)	−0.0035 (8)	0.0052 (8)
C8	0.0323 (11)	0.0314 (11)	0.0355 (11)	0.0042 (9)	−0.0043 (9)	−0.0018 (9)
C9	0.087 (2)	0.0531 (18)	0.0476 (15)	−0.0120 (16)	0.0097 (15)	0.0089 (13)
N1	0.0233 (9)	0.0331 (10)	0.0312 (9)	0.0009 (7)	0.0022 (7)	−0.0022 (8)
O1	0.0407 (10)	0.0470 (10)	0.0436 (9)	−0.0165 (8)	−0.0027 (7)	−0.0009 (8)
O2	0.0524 (10)	0.0314 (9)	0.0462 (9)	0.0083 (8)	0.0008 (8)	−0.0002 (7)
O3	0.0230 (8)	0.0514 (10)	0.0412 (9)	0.0030 (7)	−0.0015 (6)	−0.0083 (7)
Cl1	0.0513 (4)	0.0353 (3)	0.0496 (4)	−0.0104 (3)	−0.0075 (3)	−0.0046 (3)
Cl2	0.0564 (4)	0.0610 (4)	0.0348 (3)	−0.0153 (3)	0.0085 (3)	−0.0048 (3)
S1	0.0327 (3)	0.0290 (3)	0.0322 (3)	−0.0035 (2)	−0.0011 (2)	−0.0005 (2)

C1—C2	1.384 (3)	C7—N1	1.357 (3)
C1—C6	1.384 (3)	C7—C8	1.540 (3)
C1—S1	1.761 (2)	C8—Cl1	1.760 (2)
C2—C3	1.383 (4)	C8—Cl2	1.778 (2)
C2—H2	0.9300	C8—H8	0.9800
C3—C4	1.385 (4)	C9—H9A	0.9600
C3—H3	0.9300	C9—H9B	0.9600
C4—C5	1.381 (4)	C9—H9C	0.9600
C4—C9	1.512 (4)	N1—S1	1.6800 (19)
C5—C6	1.384 (4)	N1—H1N	0.82 (3)
C5—H5	0.9300	O1—S1	1.4256 (17)
C6—H6	0.9300	O2—S1	1.4276 (17)
C7—O3	1.210 (3)
C2—C1—C6	120.8 (2)	C7—C8—Cl1	109.94 (15)
C2—C1—S1	120.07 (18)	C7—C8—Cl2	109.02 (14)
C6—C1—S1	118.98 (18)	Cl1—C8—Cl2	110.02 (12)
C3—C2—C1	118.8 (2)	C7—C8—H8	109.3
C3—C2—H2	120.6	Cl1—C8—H8	109.3
C1—C2—H2	120.6	Cl2—C8—H8	109.3
C2—C3—C4	121.8 (2)	C4—C9—H9A	109.5
C2—C3—H3	119.1	C4—C9—H9B	109.5
C4—C3—H3	119.1	H9A—C9—H9B	109.5
C5—C4—C3	117.8 (2)	C4—C9—H9C	109.5
C5—C4—C9	120.5 (3)	H9A—C9—H9C	109.5
C3—C4—C9	121.7 (3)	H9B—C9—H9C	109.5
C4—C5—C6	121.9 (2)	C7—N1—S1	124.04 (15)
C4—C5—H5	119.0	C7—N1—H1N	119.4 (18)
C6—C5—H5	119.0	S1—N1—H1N	116.4 (18)
C5—C6—C1	118.7 (2)	O1—S1—O2	120.76 (11)
C5—C6—H6	120.6	O1—S1—N1	103.72 (10)
C1—C6—H6	120.6	O2—S1—N1	108.43 (10)
O3—C7—N1	124.0 (2)	O1—S1—C1	109.25 (11)
O3—C7—C8	122.60 (19)	O2—S1—C1	109.93 (11)
N1—C7—C8	113.45 (18)	N1—S1—C1	103.17 (10)
C6—C1—C2—C3	1.1 (4)	N1—C7—C8—Cl2	69.4 (2)
S1—C1—C2—C3	−175.0 (2)	O3—C7—N1—S1	−0.4 (3)
C1—C2—C3—C4	−0.5 (4)	C8—C7—N1—S1	179.19 (14)
C2—C3—C4—C5	−0.9 (4)	C7—N1—S1—O1	174.97 (17)
C2—C3—C4—C9	178.2 (3)	C7—N1—S1—O2	45.5 (2)
C3—C4—C5—C6	1.9 (4)	C7—N1—S1—C1	−71.09 (19)
C9—C4—C5—C6	−177.2 (3)	C2—C1—S1—O1	−164.08 (19)
C4—C5—C6—C1	−1.4 (4)	C6—C1—S1—O1	19.7 (2)
C2—C1—C6—C5	−0.2 (4)	C2—C1—S1—O2	−29.4 (2)
S1—C1—C6—C5	175.97 (19)	C6—C1—S1—O2	154.39 (18)
O3—C7—C8—Cl1	9.7 (3)	C2—C1—S1—N1	86.1 (2)
N1—C7—C8—Cl1	−169.93 (15)	C6—C1—S1—N1	−90.13 (19)
O3—C7—C8—Cl2	−111.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.82 (3)	2.03 (3)	2.833 (2)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.82 (3)	2.03 (3)	2.833 (2)	166 (2)

Symmetry code: (i) .