2,2-Dichloro-N-(4-chloro-phenyl-sulfon-yl)-acetamide.

In the crystal structure of the title compound (N4CPSDCAA), C(8)H(6)Cl(3)NO(3)S, the conformations of the N-H and C=O bonds in the SO(2)-NH-CO-C group are trans to each other, similar to those observed in 2,2-dichloro-N-(phenyl-sulfon-yl)-acetamide (NPSDCAA), 2,2-dichloro-N-(4-methyl-phenyl-sulfon-yl)acetamide (N4MPSDCAA) and N-(4-chloro-phenyl-sulfon-yl)-2,2,2-trimethyl-acetamide (N4CPSTMAA), with similar bond parameters. The -SNHCOC- unit in N4CPSDCAA is essentially planar and makes a dihedral angle of 79.67 (5)° with the benzene ring, comparable to 79.75 (8)° in NPSDCAA, 81.02 (5)° in N4MPSDCAA and 82.2 (1)° in N4CPSTMAA. The mol-ecules in N4CPSDCAA are linked into layers parallel to the (001) plane by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2006 ▶); Gowda, Foro, Nirmala et al. (2008 ▶); Gowda, Foro, Sowmya et al. (2008 ▶).

Experimental

Crystal data

C8H6Cl3NO3S

M = 302.55

Orthorhombic,

a = 9.5909 (5) Å

b = 10.1750 (5) Å

c = 23.256 (1) Å

V = 2269.49 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.98 mm−1

T = 299 (2) K

0.32 × 0.28 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.745, T max = 0.926

10378 measured reflections

2309 independent reflections

1642 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.073

S = 1.08

2309 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.27 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/S1600536808021715/ci2630sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021715/ci2630Isup2.hkl

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

C8H6Cl3NO3S	F000 = 1216
Mr = 302.55	Dx = 1.771 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5145 reflections
a = 9.5909 (5) Å	θ = 2.2–28.0º
b = 10.1750 (5) Å	µ = 0.98 mm−1
c = 23.256 (1) Å	T = 299 (2) K
V = 2269.49 (19) Å3	Plate, colourless
Z = 8	0.32 × 0.28 × 0.08 mm

Oxford Diffraction Xcalibur diffractometer	2309 independent reflections
Radiation source: fine-focus sealed tube	1642 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 299(2) K	θmax = 26.4º
ω and φ scans	θmin = 3.1º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −11→11
Tmin = 0.745, Tmax = 0.926	k = −10→12
10378 measured reflections	l = −28→29

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)] = 0.027	H-atom parameters constrained
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0279P)2 + 1.2816P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
2309 reflections	Δρmax = 0.34 e Å−3
145 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.1931 (2)	0.2061 (2)	0.10986 (9)	0.0312 (5)
C2	0.0826 (2)	0.2583 (2)	0.07911 (10)	0.0397 (6)
H2	−0.0087	0.2353	0.0882	0.048*
C3	0.1095 (3)	0.3449 (3)	0.03482 (11)	0.0464 (6)
H3	0.0364	0.3802	0.0136	0.056*
C4	0.2445 (3)	0.3787 (2)	0.02219 (9)	0.0431 (6)
C5	0.3549 (3)	0.3264 (3)	0.05226 (10)	0.0471 (6)
H5	0.4458	0.3499	0.0430	0.056*
C6	0.3295 (2)	0.2384 (2)	0.09643 (10)	0.0405 (6)
H6	0.4031	0.2015	0.1168	0.049*
C7	0.2795 (2)	0.2659 (2)	0.24629 (9)	0.0275 (5)
C8	0.2532 (2)	0.3590 (2)	0.29700 (9)	0.0332 (5)
H8	0.1789	0.4210	0.2869	0.040*
N1	0.16103 (17)	0.21068 (16)	0.22462 (7)	0.0283 (4)
H1N	0.0830	0.2314	0.2404	0.034*
O1	0.01558 (16)	0.06430 (16)	0.16706 (7)	0.0436 (4)
O2	0.26697 (17)	0.01306 (15)	0.17698 (7)	0.0424 (4)
O3	0.39439 (14)	0.24435 (16)	0.22705 (6)	0.0379 (4)
Cl1	0.27646 (9)	0.48942 (8)	−0.03310 (3)	0.0686 (2)
Cl2	0.40650 (7)	0.44634 (6)	0.31294 (3)	0.04543 (17)
Cl3	0.20101 (7)	0.26485 (7)	0.35760 (2)	0.04963 (19)
S1	0.15710 (6)	0.10591 (5)	0.16960 (2)	0.03174 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0315 (12)	0.0341 (12)	0.0280 (11)	−0.0011 (9)	0.0005 (9)	−0.0033 (9)
C2	0.0314 (12)	0.0452 (14)	0.0425 (13)	−0.0007 (11)	−0.0017 (10)	0.0020 (11)
C3	0.0477 (15)	0.0485 (15)	0.0431 (14)	0.0070 (12)	−0.0074 (12)	0.0085 (12)
C4	0.0581 (16)	0.0403 (14)	0.0310 (12)	−0.0046 (12)	0.0046 (12)	0.0020 (11)
C5	0.0397 (14)	0.0629 (17)	0.0386 (13)	−0.0102 (13)	0.0071 (11)	−0.0001 (12)
C6	0.0312 (13)	0.0557 (15)	0.0346 (12)	−0.0004 (11)	−0.0008 (10)	0.0001 (11)
C7	0.0255 (12)	0.0289 (11)	0.0280 (10)	0.0023 (9)	−0.0023 (9)	0.0051 (9)
C8	0.0322 (12)	0.0322 (12)	0.0352 (11)	0.0030 (9)	−0.0028 (10)	−0.0014 (10)
N1	0.0200 (9)	0.0353 (10)	0.0296 (9)	0.0004 (7)	0.0020 (7)	−0.0014 (8)
O1	0.0366 (9)	0.0498 (10)	0.0443 (9)	−0.0153 (8)	−0.0038 (7)	0.0004 (8)
O2	0.0464 (10)	0.0329 (9)	0.0481 (10)	0.0080 (8)	−0.0005 (8)	−0.0007 (7)
O3	0.0220 (8)	0.0523 (10)	0.0394 (9)	0.0023 (7)	−0.0003 (7)	−0.0074 (8)
Cl1	0.0915 (6)	0.0667 (5)	0.0475 (4)	−0.0120 (4)	0.0065 (4)	0.0189 (4)
Cl2	0.0487 (4)	0.0371 (3)	0.0505 (4)	−0.0099 (3)	−0.0066 (3)	−0.0048 (3)
Cl3	0.0497 (4)	0.0641 (4)	0.0350 (3)	−0.0146 (3)	0.0070 (3)	−0.0037 (3)
S1	0.0303 (3)	0.0313 (3)	0.0337 (3)	−0.0030 (2)	−0.0011 (2)	−0.0007 (2)

C1—C6	1.385 (3)	C6—H6	0.93
C1—C2	1.385 (3)	C7—O3	1.209 (2)
C1—S1	1.757 (2)	C7—N1	1.364 (3)
C2—C3	1.380 (3)	C7—C8	1.534 (3)
C2—H2	0.93	C8—Cl2	1.758 (2)
C3—C4	1.371 (4)	C8—Cl3	1.776 (2)
C3—H3	0.93	C8—H8	0.98
C4—C5	1.376 (4)	N1—S1	1.6659 (17)
C4—Cl1	1.737 (2)	N1—H1N	0.86
C5—C6	1.384 (3)	O1—S1	1.4230 (16)
C5—H5	0.93	O2—S1	1.4257 (16)
C6—C1—C2	121.0 (2)	O3—C7—N1	123.20 (19)
C6—C1—S1	120.11 (17)	O3—C7—C8	123.12 (19)
C2—C1—S1	118.73 (17)	N1—C7—C8	113.68 (17)
C3—C2—C1	119.2 (2)	C7—C8—Cl2	109.69 (15)
C3—C2—H2	120.4	C7—C8—Cl3	108.86 (15)
C1—C2—H2	120.4	Cl2—C8—Cl3	109.94 (12)
C4—C3—C2	119.8 (2)	C7—C8—H8	109.4
C4—C3—H3	120.1	Cl2—C8—H8	109.4
C2—C3—H3	120.1	Cl3—C8—H8	109.4
C3—C4—C5	121.3 (2)	C7—N1—S1	124.49 (15)
C3—C4—Cl1	119.2 (2)	C7—N1—H1N	117.8
C5—C4—Cl1	119.4 (2)	S1—N1—H1N	117.8
C4—C5—C6	119.5 (2)	O1—S1—O2	120.86 (10)
C4—C5—H5	120.3	O1—S1—N1	104.11 (9)
C6—C5—H5	120.3	O2—S1—N1	108.35 (9)
C5—C6—C1	119.2 (2)	O1—S1—C1	109.09 (10)
C5—C6—H6	120.4	O2—S1—C1	109.54 (10)
C1—C6—H6	120.4	N1—S1—C1	103.40 (9)
C6—C1—C2—C3	−0.7 (3)	N1—C7—C8—Cl3	70.2 (2)
S1—C1—C2—C3	175.18 (18)	O3—C7—N1—S1	0.5 (3)
C1—C2—C3—C4	−0.5 (4)	C8—C7—N1—S1	179.96 (14)
C2—C3—C4—C5	1.1 (4)	C7—N1—S1—O1	173.55 (16)
C2—C3—C4—Cl1	−179.21 (19)	C7—N1—S1—O2	43.71 (19)
C3—C4—C5—C6	−0.4 (4)	C7—N1—S1—C1	−72.47 (18)
Cl1—C4—C5—C6	179.85 (19)	C6—C1—S1—O1	−167.61 (18)
C4—C5—C6—C1	−0.7 (4)	C2—C1—S1—O1	16.5 (2)
C2—C1—C6—C5	1.3 (3)	C6—C1—S1—O2	−33.3 (2)
S1—C1—C6—C5	−174.49 (18)	C2—C1—S1—O2	150.84 (17)
O3—C7—C8—Cl2	10.0 (3)	C6—C1—S1—N1	82.0 (2)
N1—C7—C8—Cl2	−169.47 (14)	C2—C1—S1—N1	−93.83 (19)
O3—C7—C8—Cl3	−110.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86	1.97	2.814 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86	1.97	2.814 (2)	169

Symmetry code: (i) .