2,2-Dichloro-N-(phenyl­sulfon­yl)­acetamide

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

doi:10.1107/S1600536808021831

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1522

doi:10.1107/S1600536808021831

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2,2-Dichloro-N-(phenylsulfonyl)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 13 July 2008; online 19 July 2008)

The conformation of the N—H and C=O bonds in the title compound, C₈H₇Cl₂NO₃S, is trans. The benzene ring and the SO₂—NH—CO—C group form a dihedral angle of 79.75 (8)°. Molecules are connected via N—H⋯O hydrogen bonds to form linear supramolecular 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_r = 268.11
Orthorhombic, P b c a
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 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) 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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.127
S = 1.13
2156 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.61 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	2.00	2.844 (3)	166
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/S1600536808021831/tk2284sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021831/tk2284Isup2.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 (Gowda et al., 2006, 2007, 2008a,b; Gowda, Foro, Nirmala et al., 2008), the structure of N-(phenylsulfonyl)-2,2-dichloroacetamide (I) has been determined. The conformation of the N—H and C=O bonds is trans (Fig. 1), similar to that observed in N-(phenylsulfonyl)-2,2,2-trimethylacetamide (Gowda et al., 2008b), N-(4-methylphenylsulfonyl)- 2,2-dichloroacetamide (Gowda, Foro, Nirmala et al., 2008) and (4-methylphenylsulfonyl)-2,2,2-trimethylacetamide (Gowda et al., 2008a). Further, the bond parameters in (I) are similar to those in the aforementioned structures and in each of N-(aryl)-2,2-dichloroacetamides (Gowda et al., 2006) and benzenesulfonamide (Gowda et al., 2007). The crystal packing diagram of (I) is dominated by N—H···O hydrogen bonds (Table 1) that lead to supramolecular chains that stack to form layers, as shown in Fig. 2.

Related literature top

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

Experimental top

Compound (I) was prepared by refluxing benzenesulfonamide (0.10 mole) with an excess of 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. Compound (I) was precipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. Single crystals used for X-ray diffraction studies were obtained from the slow evaporation of an ethanolic solution of (I).

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 (I), showing the atom labeling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. View of the molecular packing in (I) with hydrogen bonding shown as dashed lines.

2,2-Dichloro-N-(phenylsulfonyl)acetamide top

Crystal data top

C₈H₇Cl₂NO₃S	F(000) = 1088
M_r = 268.11	D_x = 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 = 2.8–27.9°
b = 10.462 (1) Å	µ = 0.79 mm⁻¹
c = 21.024 (2) Å	T = 299 K
V = 2126.7 (4) Å³	Prism, colourless
Z = 8	0.48 × 0.48 × 0.40 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2156 independent reflections
Radiation source: fine-focus sealed tube	1729 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −11→12
T_min = 0.689, T_max = 0.728	k = −12→13
9241 measured reflections	l = −24→25

Refinement top

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0496P)² + 3.3191P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.005
2156 reflections	Δρ_max = 0.46 e Å⁻³
137 parameters	Δρ_min = −0.61 e Å⁻³
0 restraints	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)

Crystal data top

C₈H₇Cl₂NO₃S	V = 2126.7 (4) Å³
M_r = 268.11	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.669 (1) Å	µ = 0.79 mm⁻¹
b = 10.462 (1) Å	T = 299 K
c = 21.024 (2) Å	0.48 × 0.48 × 0.40 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2156 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1729 reflections with I > 2σ(I)
T_min = 0.689, T_max = 0.728	R_int = 0.038
9241 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.13	Δρ_max = 0.46 e Å⁻³
2156 reflections	Δρ_min = −0.61 e Å⁻³
137 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	0.2304 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₈H₇Cl₂NO₃S
M_r	268.11
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	299
a, b, c (Å)	9.669 (1), 10.462 (1), 21.024 (2)
V (Å³)	2126.7 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.48 × 0.48 × 0.40

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.689, 0.728
No. of measured, independent and observed [I > 2σ(I)] reflections	9241, 2156, 1729
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.127, 1.13
No. of reflections	2156
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.61

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	2.00	2.844 (3)	166

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

Gowda, B. T., Foro, S., Nirmala, P. G., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1492. Web of Science CSD CrossRef IUCr Journals Google Scholar
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