2,2-Dichloro-N-(4-chloro­phenyl­sulfon­yl)­acetamide

Gowda, B.T.; Foro, S.; Nirmala, P.G.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808021715

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1521

doi:10.1107/S1600536808021715

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2,2-Dichloro-N-(4-chlorophenylsulfonyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala,^a B. P. Sowmya ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 11 July 2008; accepted 12 July 2008; online 19 July 2008)

In the crystal structure of the title compound (N4CPSDCAA), C₈H₆Cl₃NO₃S, the conformations of the N—H and C=O bonds in the SO₂—NH—CO—C group are trans to each other, similar to those observed in 2,2-dichloro-N-(phenylsulfonyl)acetamide (NPSDCAA), 2,2-dichloro-N-(4-methylphenylsulfonyl)acetamide (N4MPSDCAA) and N-(4-chlorophenylsulfonyl)-2,2,2-trimethylacetamide (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 molecules in N4CPSDCAA are linked into layers parallel to the (001) plane by intermolecular 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_r = 302.55
Orthorhombic, P b c a
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 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) 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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.073
S = 1.08
2309 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021715/ci2630sup1.cif

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

checkCIF report

Comment top

As part of a study of the substituent effects on the crystal structures of N-(aryl)-sulfonamides and substituted amides, in the present work, the structure of N-(4-chlorophenylsulfonyl)-2,2-dichloroacetamide (N4CPSDCAA) has been determined (Gowda et al., 2003, 2006; Gowda, Foro, Nirmala et al., 2008; Gowda, Foro, Sowmya et al., 2008). The conformations of the N—H and C═O bonds of the SO₂—NH—CO—C group in N4CPSDCAA are trans to each other (Fig. 1), similar to those observed in N-(phenylsulfonyl)-2,2-dichloroacetamide (NPSDCAA), N-(4-methylphenylsulfonyl)-2,2-dichloroacetamide (N4MPSDCAA) (Gowda, Foro, Nirmala et al., 2008) and (4-chlorophenylsulfonyl)-2,2,2- trimethylacetamide (N4CPSTMAA) (Gowda, Foro, Sowmya et al., 2008). The bond parameters in N4CPSDCAA are similar to those in NPSDCAA, N4MPSDCAA, N4CPSTMAA (Gowda, Foro, Nirmala et al., 2008; Gowda, Foro, Sowmya et al., 2008), N-(aryl)-2,2-dichloro- acetamides (Gowda et al., 2006) and 4-chlorobenzenesulfonamide (Gowda et al., 2003).

The packing diagram of N4CPSDCAA showing the N—H···O hydrogen bonds (Table 1) involved in the formation of layers parallel to the (0 0 1) plane is shown in Fig. 2.

Related literature top

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

Experimental top

The title compound was prepared by refluxing 4-chlorobenzenesulfonamide (0.10 mole) with excess dichloroacetyl chloride (0.20 mole) for about an hour on a water bath. The reaction mixture was cooled and poured into ice cold water. The resulting solid was separated, washed thoroughly with water and dissolved in warm dilute sodium hydrogen carbonate solution. The title compound was precipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound used for X-ray diffraction studies were obtained by slow evaporation of an ethanolic solution.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

2,2-Dichloro-N-(4-chlorophenylsulfonyl)acetamide top

Crystal data top

C₈H₆Cl₃NO₃S	F(000) = 1216
M_r = 302.55	D_x = 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 = 2.2–28.0°
b = 10.1750 (5) Å	µ = 0.98 mm⁻¹
c = 23.256 (1) Å	T = 299 K
V = 2269.49 (19) Å³	Plate, colourless
Z = 8	0.32 × 0.28 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2309 independent reflections
Radiation source: fine-focus sealed tube	1642 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω and ϕ scans	θ_max = 26.4°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −11→11
T_min = 0.745, T_max = 0.926	k = −10→12
10378 measured reflections	l = −28→29

Refinement top

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0279P)² + 1.2816P] where P = (F_o² + 2F_c²)/3
2309 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₈H₆Cl₃NO₃S	V = 2269.49 (19) Å³
M_r = 302.55	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.5909 (5) Å	µ = 0.98 mm⁻¹
b = 10.1750 (5) Å	T = 299 K
c = 23.256 (1) Å	0.32 × 0.28 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2309 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1642 reflections with I > 2σ(I)
T_min = 0.745, T_max = 0.926	R_int = 0.020
10378 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.09	Δρ_max = 0.34 e Å⁻³
2309 reflections	Δρ_min = −0.27 e Å⁻³
145 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₈H₆Cl₃NO₃S
M_r	302.55
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	299
a, b, c (Å)	9.5909 (5), 10.1750 (5), 23.256 (1)
V (Å³)	2269.49 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.32 × 0.28 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.745, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	10378, 2309, 1642
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.073, 1.09
No. of reflections	2309
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.27

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, y, −z+1/2.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

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