2,2-Dichloro-N-(phenyl-sulfon-yl)-acetamide.

The conformation of the N-H and C=O bonds in the title compound, C(8)H(7)Cl(2)NO(3)S, is trans. The benzene ring and the SO(2)-NH-CO-C group form a dihedral angle of 79.75 (8)°. Mol-ecules are connected via N-H⋯O hydrogen bonds to form linear supra-molecular chains.

Related literature

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

Experimental

Crystal data

C8H7Cl2NO3S

M = 268.11

Orthorhombic,

a = 9.669 (1) Å

b = 10.462 (1) Å

c = 21.024 (2) Å

V = 2126.7 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.79 mm−1

T = 299 (2) K

0.48 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.689, T max = 0.728

9241 measured reflections

2156 independent reflections

1729 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.13

2156 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.61 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/S1600536808021831/tk2284sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021831/tk2284Isup2.hkl

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

C8H7Cl2NO3S	F000 = 1088
Mr = 268.11	Dx = 1.675 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3214 reflections
a = 9.669 (1) Å	θ = 2.8–27.9º
b = 10.462 (1) Å	µ = 0.79 mm−1
c = 21.024 (2) Å	T = 299 (2) K
V = 2126.7 (4) Å3	Prism, colourless
Z = 8	0.48 × 0.48 × 0.40 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2156 independent reflections
Radiation source: fine-focus sealed tube	1729 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.9º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −11→12
Tmin = 0.689, Tmax = 0.728	k = −12→13
9241 measured reflections	l = −24→25

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.0496P)2 + 3.3191P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.127	(Δ/σ)max = 0.005
S = 1.13	Δρmax = 0.46 e Å−3
2156 reflections	Δρmin = −0.61 e Å−3
137 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: 0.0159 (14)
Secondary atom site location: difference Fourier map

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	0.2304 (3)	0.7731 (3)	0.09583 (13)	0.0374 (7)
C2	0.3659 (4)	0.7611 (4)	0.07699 (17)	0.0546 (9)
H2	0.4258	0.7074	0.0990	0.066*
C3	0.4121 (4)	0.8294 (4)	0.0250 (2)	0.0686 (12)
H3	0.5043	0.8235	0.0127	0.082*
C4	0.3236 (5)	0.9055 (4)	−0.00819 (18)	0.0663 (11)
H4	0.3542	0.9468	−0.0447	0.080*
C5	0.1901 (5)	0.9217 (4)	0.0117 (2)	0.0742 (13)
H5	0.1316	0.9773	−0.0100	0.089*
C6	0.1421 (4)	0.8553 (4)	0.06421 (18)	0.0615 (10)
H6	0.0515	0.8658	0.0780	0.074*
C7	0.2865 (3)	0.8421 (3)	0.24530 (13)	0.0315 (6)
C8	0.2599 (3)	0.9313 (3)	0.30181 (14)	0.0383 (7)
H8	0.1815	0.9875	0.2923	0.046*
N1	0.1690 (2)	0.7905 (2)	0.22078 (11)	0.0317 (5)
H1N	0.0909	0.8132	0.2368	0.038*
O1	0.0258 (2)	0.6569 (2)	0.15258 (11)	0.0517 (6)
O2	0.2658 (2)	0.5866 (2)	0.17518 (11)	0.0474 (6)
O3	0.40112 (19)	0.8193 (2)	0.22517 (10)	0.0425 (5)
Cl1	0.40794 (9)	1.02379 (8)	0.31696 (4)	0.0542 (3)
Cl2	0.22066 (11)	0.83545 (10)	0.36880 (4)	0.0626 (3)
S1	0.16902 (7)	0.68542 (7)	0.16113 (3)	0.0355 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0444 (16)	0.0402 (16)	0.0275 (13)	0.0016 (13)	−0.0022 (12)	−0.0021 (12)
C2	0.0468 (18)	0.069 (2)	0.0481 (19)	0.0057 (18)	0.0038 (15)	0.0114 (17)
C3	0.060 (2)	0.088 (3)	0.059 (2)	−0.001 (2)	0.0103 (19)	0.018 (2)
C4	0.086 (3)	0.073 (3)	0.0405 (19)	−0.007 (2)	0.0074 (19)	0.0124 (18)
C5	0.092 (3)	0.074 (3)	0.057 (2)	0.024 (3)	−0.002 (2)	0.024 (2)
C6	0.059 (2)	0.077 (3)	0.0480 (19)	0.025 (2)	0.0045 (17)	0.0120 (18)
C7	0.0317 (14)	0.0342 (13)	0.0285 (13)	0.0023 (11)	−0.0048 (11)	0.0012 (11)
C8	0.0379 (14)	0.0392 (16)	0.0377 (15)	0.0014 (13)	−0.0053 (12)	−0.0059 (12)
N1	0.0231 (10)	0.0409 (13)	0.0310 (11)	0.0013 (9)	0.0000 (9)	−0.0042 (10)
O1	0.0397 (12)	0.0637 (15)	0.0517 (13)	−0.0144 (11)	−0.0074 (10)	−0.0088 (11)
O2	0.0553 (13)	0.0384 (12)	0.0486 (12)	0.0084 (10)	0.0025 (11)	0.0014 (10)
O3	0.0247 (10)	0.0621 (14)	0.0407 (11)	0.0015 (9)	−0.0020 (8)	−0.0080 (10)
Cl1	0.0589 (5)	0.0460 (5)	0.0577 (5)	−0.0117 (4)	−0.0141 (4)	−0.0070 (4)
Cl2	0.0783 (7)	0.0726 (6)	0.0369 (4)	−0.0188 (5)	0.0138 (4)	−0.0085 (4)
S1	0.0355 (4)	0.0372 (4)	0.0338 (4)	−0.0009 (3)	−0.0024 (3)	−0.0022 (3)

C1—C2	1.375 (5)	C6—H6	0.9300
C1—C6	1.382 (5)	C7—O3	1.210 (3)
C1—S1	1.755 (3)	C7—N1	1.359 (3)
C2—C3	1.380 (5)	C7—C8	1.533 (4)
C2—H2	0.9300	C8—Cl1	1.757 (3)
C3—C4	1.361 (6)	C8—Cl2	1.770 (3)
C3—H3	0.9300	C8—H8	0.9800
C4—C5	1.368 (6)	N1—S1	1.668 (2)
C4—H4	0.9300	N1—H1N	0.8600
C5—C6	1.384 (6)	O1—S1	1.428 (2)
C5—H5	0.9300	O2—S1	1.425 (2)
C2—C1—C6	120.5 (3)	O3—C7—N1	123.7 (3)
C2—C1—S1	120.0 (2)	O3—C7—C8	123.0 (2)
C6—C1—S1	119.5 (3)	N1—C7—C8	113.3 (2)
C1—C2—C3	119.3 (3)	C7—C8—Cl1	109.8 (2)
C1—C2—H2	120.3	C7—C8—Cl2	107.9 (2)
C3—C2—H2	120.3	Cl1—C8—Cl2	110.02 (16)
C4—C3—C2	120.4 (4)	C7—C8—H8	109.7
C4—C3—H3	119.8	Cl1—C8—H8	109.7
C2—C3—H3	119.8	Cl2—C8—H8	109.7
C3—C4—C5	120.6 (4)	C7—N1—S1	123.15 (19)
C3—C4—H4	119.7	C7—N1—H1N	118.4
C5—C4—H4	119.7	S1—N1—H1N	118.4
C4—C5—C6	119.8 (4)	O2—S1—O1	120.73 (15)
C4—C5—H5	120.1	O2—S1—N1	108.81 (13)
C6—C5—H5	120.1	O1—S1—N1	103.44 (13)
C1—C6—C5	119.3 (4)	O2—S1—C1	108.64 (14)
C1—C6—H6	120.4	O1—S1—C1	109.80 (15)
C5—C6—H6	120.4	N1—S1—C1	104.10 (13)
C6—C1—C2—C3	−1.7 (6)	O3—C7—N1—S1	2.0 (4)
S1—C1—C2—C3	179.2 (3)	C8—C7—N1—S1	−177.32 (19)
C1—C2—C3—C4	−1.7 (7)	C7—N1—S1—O2	49.4 (3)
C2—C3—C4—C5	4.2 (7)	C7—N1—S1—O1	178.9 (2)
C3—C4—C5—C6	−3.3 (7)	C7—N1—S1—C1	−66.3 (3)
C2—C1—C6—C5	2.5 (6)	C2—C1—S1—O2	−15.1 (3)
S1—C1—C6—C5	−178.3 (3)	C6—C1—S1—O2	165.7 (3)
C4—C5—C6—C1	0.0 (7)	C2—C1—S1—O1	−149.1 (3)
O3—C7—C8—Cl1	15.7 (4)	C6—C1—S1—O1	31.7 (3)
N1—C7—C8—Cl1	−164.9 (2)	C2—C1—S1—N1	100.7 (3)
O3—C7—C8—Cl2	−104.2 (3)	C6—C1—S1—N1	−78.5 (3)
N1—C7—C8—Cl2	75.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86	2.00	2.844 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86	2.00	2.844 (3)	166

Symmetry code: (i) .