N-(Phenyl­sulfon­yl)acetamide

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

doi:10.1107/S1600536810015849

organic compounds

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Volume 66| Part 6| June 2010| Page o1284

https://doi.org/10.1107/S1600536810015849

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N-(Phenylsulfonyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala ^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 28 April 2010; accepted 29 April 2010; online 8 May 2010)

In the title compound, C₈H₉NO₃S, the N—H bond is in an antiperiplanar conformation with respect to the C=O bond. The crystal packing is stabilized by N—H⋯O hydrogen bonds, generating C(4) chains propagating in [001].

Related literature

Sulfonamide drugs contain the sulfanilamide moiety, see: Maren (1976 ). The propensity for hydrogen bonding in the solid state, due to the presence of various hydrogen bond donors and acceptors, can give rise to polymorphism, see: Yang & Guillory (1972 ). For the hydrogen-bonding preferences of sulfonamides, see: Adsmond & Grant (2001 ). For related structures, see: Gowda et al. (2008a ,b , 2009 ).

Experimental

Crystal data

C₈H₉NO₃S
M_r = 199.22
Tetragonal, P 4₃
a = 7.9400 (5) Å
c = 15.288 (2) Å
V = 963.81 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 299 K
0.30 × 0.24 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.913, T_max = 0.964
2706 measured reflections
1401 independent reflections
1214 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.100
S = 1.30
1401 reflections
121 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 378 Friedel pairs
Flack parameter: 0.11 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.85 (2)	2.02 (3)	2.823 (5)	156 (5)
Symmetry code: (i) $[y, -x+1, z+{\script{1\over 4}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810015849/bt5256sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015849/bt5256Isup2.hkl

checkCIF report

Comment top

Sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976). The propensity for hydrogen bonding in the solid state, due to the presence of various hydrogen bond donors and acceptors can give rise to polymorphism (Yang & Guillory, 1972). The hydrogen bonding preferences of sulfonamides has also been investigated (Adsmond & Grant, 2001). The nature and position of substituents play a significant role on the crystal structures of N-(aryl)sulfonoamides (Gowda et al., 2008a,b, 2009). As a part of studying the substituent effects on the structures of this class of compounds, the structure of N-(phenylsulfonyl)-acetamide (I) has been determined. The conformations of the N—H and C=O bonds of the SO₂—NH—CO—C segment in the structure are anti to each other (Fig. 1), similar to that observed in N-(phenylsulfonyl)-2,2-dimethylacetamide (II)(Gowda et al., 2009), N-(phenylsulfonyl)-2,2,2- trimethylacetamide (III)(Gowda et al., 2008b) and N-(phenylsulfonyl)-2,2-dichloroacetamide (IV) (Gowda et al., 2008a).

The C7—N1 bond in the C—SO₂—NH—C segment of (I) is gauche [C7—N1—S1—O2 = 58.3 (5)°] with respect to the S1═O1 bond and anti with respect to the S1═O2 bond [C7—N1—S1—O1 = -172.6 (4)°]. The molecule in (I) is bent at the S-atom with a C1—S1—N1—C7 torsion angle of -58.8 (4)°, compared to the value of 67.1 (3)° in (II) and -66.3 (3)° in (IV),

The packing of molecules linked by N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

Sulfonamide drugs contain the sulfanilamide moiety, see: Maren (1976). The propensity for hydrogen bonding in the solid state, due to the presence of various hydrogen bond donors and acceptors, can give rise to polymorphism, see: Yang & Guillory (1972). For the hydrogen-bonding preferences of sulfonamides, see: Adsmond & Grant (2001). For related structures, see: Gowda et al. (2008a,b, 2009).

Experimental top

The title compound was prepared by refluxing benzenesulfonamide (0.10 mole) with an excess of acetyl 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 reprecipitated 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 spectra.

Rod like colorless single crystals were obtained from a slow evaporation of an ethanolic solution of the compound.

Structure description top

The packing of molecules linked by N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Sulfonamide drugs contain the sulfanilamide moiety, see: Maren (1976). The propensity for hydrogen bonding in the solid state, due to the presence of various hydrogen bond donors and acceptors, can give rise to polymorphism, see: Yang & Guillory (1972). For the hydrogen-bonding preferences of sulfonamides, see: Adsmond & Grant (2001). For related structures, see: Gowda et al. (2008a,b, 2009).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

N-(Phenylsulfonyl)acetamide top

Crystal data top

C₈H₉NO₃S	D_x = 1.373 Mg m⁻³
M_r = 199.22	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃	Cell parameters from 1337 reflections
Hall symbol: P 4cw	θ = 2.6–27.9°
a = 7.9400 (5) Å	µ = 0.31 mm⁻¹
c = 15.288 (2) Å	T = 299 K
V = 963.81 (15) Å³	Rod, colourless
Z = 4	0.30 × 0.24 × 0.12 mm
F(000) = 416

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1401 independent reflections
Radiation source: fine-focus sealed tube	1214 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Rotation method data acquisition using ω and φ scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→9
T_min = 0.913, T_max = 0.964	k = −9→5
2706 measured reflections	l = −18→19

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0165P)² + 0.6175P] where P = (F_o² + 2F_c²)/3
S = 1.30	(Δ/σ)_max = 0.022
1401 reflections	Δρ_max = 0.21 e Å⁻³
121 parameters	Δρ_min = −0.24 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 378 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.11 (16)

Crystal data top

C₈H₉NO₃S	Z = 4
M_r = 199.22	Mo Kα radiation
Tetragonal, P4₃	µ = 0.31 mm⁻¹
a = 7.9400 (5) Å	T = 299 K
c = 15.288 (2) Å	0.30 × 0.24 × 0.12 mm
V = 963.81 (15) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1401 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1214 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.964	R_int = 0.014
2706 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	Δρ_max = 0.21 e Å⁻³
S = 1.30	Δρ_min = −0.24 e Å⁻³
1401 reflections	Absolute structure: Flack (1983), 378 Friedel pairs
121 parameters	Absolute structure parameter: 0.11 (16)
2 restraints

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.1027 (6)	0.4526 (6)	−0.0895 (3)	0.0558 (12)
C2	0.1149 (6)	0.4033 (7)	−0.1756 (3)	0.0646 (14)
H2	0.1204	0.2895	−0.1896	0.078*
C3	0.1188 (7)	0.5227 (9)	−0.2413 (4)	0.0866 (18)
H3	0.1238	0.4899	−0.2996	0.104*
C4	0.1154 (8)	0.6897 (9)	−0.2194 (5)	0.099 (2)
H4	0.1202	0.7704	−0.2635	0.119*
C5	0.1051 (9)	0.7400 (8)	−0.1344 (7)	0.108 (3)
H5	0.1017	0.8542	−0.1209	0.129*
C6	0.0996 (7)	0.6210 (9)	−0.0676 (5)	0.0869 (19)
H6	0.0939	0.6543	−0.0093	0.104*
C7	0.4226 (6)	0.3105 (6)	0.0165 (3)	0.0550 (12)
C8	0.5621 (6)	0.3530 (7)	0.0779 (4)	0.0792 (17)
H8A	0.5555	0.2816	0.1285	0.095*
H8B	0.5523	0.4686	0.0956	0.095*
H8C	0.6684	0.3361	0.0492	0.095*
N1	0.2655 (5)	0.3259 (5)	0.0517 (2)	0.0543 (10)
H1N	0.250 (6)	0.373 (6)	0.1013 (19)	0.065*
O1	−0.0383 (4)	0.3502 (6)	0.0542 (3)	0.0969 (14)
O2	0.0878 (5)	0.1384 (5)	−0.0435 (2)	0.0849 (13)
O3	0.4421 (5)	0.2652 (5)	−0.0584 (2)	0.0725 (11)
S1	0.08988 (14)	0.30118 (19)	−0.00585 (8)	0.0633 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.048 (3)	0.059 (3)	0.060 (3)	0.004 (2)	−0.007 (2)	−0.015 (3)
C2	0.066 (3)	0.070 (3)	0.057 (3)	0.004 (3)	−0.008 (3)	−0.014 (3)
C3	0.089 (5)	0.098 (5)	0.073 (4)	0.002 (3)	−0.017 (3)	0.007 (4)
C4	0.088 (5)	0.088 (5)	0.122 (6)	−0.005 (4)	−0.026 (4)	0.023 (5)
C5	0.115 (6)	0.059 (4)	0.149 (7)	0.003 (4)	−0.028 (5)	−0.020 (5)
C6	0.084 (4)	0.084 (5)	0.093 (4)	−0.002 (3)	−0.017 (4)	−0.028 (4)
C7	0.046 (3)	0.057 (3)	0.062 (3)	0.004 (2)	0.005 (2)	0.004 (2)
C8	0.043 (3)	0.105 (4)	0.089 (4)	0.003 (3)	−0.005 (3)	−0.001 (4)
N1	0.041 (2)	0.079 (3)	0.043 (2)	−0.0046 (18)	0.0041 (18)	−0.017 (2)
O1	0.0412 (19)	0.173 (4)	0.077 (2)	−0.004 (2)	0.009 (2)	−0.017 (3)
O2	0.109 (3)	0.073 (3)	0.074 (2)	−0.029 (2)	−0.019 (2)	−0.012 (2)
O3	0.069 (2)	0.090 (3)	0.059 (2)	0.019 (2)	0.0191 (18)	0.0000 (19)
S1	0.0454 (6)	0.0888 (10)	0.0557 (6)	−0.0127 (6)	−0.0023 (7)	−0.0144 (7)

Geometric parameters (Å, º) top

C1—C6	1.378 (7)	C6—H6	0.9300
C1—C2	1.377 (6)	C7—O3	1.210 (5)
C1—S1	1.758 (5)	C7—N1	1.365 (6)
C2—C3	1.380 (7)	C7—C8	1.491 (6)
C2—H2	0.9300	C8—H8A	0.9600
C3—C4	1.367 (9)	C8—H8B	0.9600
C3—H3	0.9300	C8—H8C	0.9600
C4—C5	1.363 (9)	N1—S1	1.660 (4)
C4—H4	0.9300	N1—H1N	0.854 (19)
C5—C6	1.393 (10)	O1—S1	1.425 (4)
C5—H5	0.9300	O2—S1	1.415 (4)

C6—C1—C2	120.7 (5)	O3—C7—N1	121.1 (5)
C6—C1—S1	119.0 (5)	O3—C7—C8	124.7 (5)
C2—C1—S1	120.3 (4)	N1—C7—C8	114.2 (4)
C3—C2—C1	120.1 (5)	C7—C8—H8A	109.5
C3—C2—H2	120.0	C7—C8—H8B	109.5
C1—C2—H2	120.0	H8A—C8—H8B	109.5
C4—C3—C2	119.2 (6)	C7—C8—H8C	109.5
C4—C3—H3	120.4	H8A—C8—H8C	109.5
C2—C3—H3	120.4	H8B—C8—H8C	109.5
C5—C4—C3	121.2 (7)	C7—N1—S1	123.2 (3)
C5—C4—H4	119.4	C7—N1—H1N	122 (3)
C3—C4—H4	119.4	S1—N1—H1N	113 (3)
C4—C5—C6	120.2 (6)	O2—S1—O1	120.2 (2)
C4—C5—H5	119.9	O2—S1—N1	109.5 (2)
C6—C5—H5	119.9	O1—S1—N1	103.1 (2)
C1—C6—C5	118.6 (6)	O2—S1—C1	109.2 (2)
C1—C6—H6	120.7	O1—S1—C1	108.8 (3)
C5—C6—H6	120.7	N1—S1—C1	104.8 (2)

C6—C1—C2—C3	−2.0 (8)	C7—N1—S1—O2	58.3 (5)
S1—C1—C2—C3	177.7 (4)	C7—N1—S1—O1	−172.6 (4)
C1—C2—C3—C4	1.9 (8)	C7—N1—S1—C1	−58.8 (4)
C2—C3—C4—C5	−1.2 (11)	C6—C1—S1—O2	177.4 (4)
C3—C4—C5—C6	0.7 (12)	C2—C1—S1—O2	−2.3 (5)
C2—C1—C6—C5	1.5 (8)	C6—C1—S1—O1	44.4 (5)
S1—C1—C6—C5	−178.3 (5)	C2—C1—S1—O1	−135.3 (4)
C4—C5—C6—C1	−0.8 (10)	C6—C1—S1—N1	−65.3 (4)
O3—C7—N1—S1	−5.6 (7)	C2—C1—S1—N1	114.9 (4)
C8—C7—N1—S1	174.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.85 (2)	2.02 (3)	2.823 (5)	156 (5)

Symmetry code: (i) y, −x+1, z+1/4.

Experimental details

Crystal data
Chemical formula	C₈H₉NO₃S
M_r	199.22
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	299
a, c (Å)	7.9400 (5), 15.288 (2)
V (Å³)	963.81 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.30 × 0.24 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.913, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	2706, 1401, 1214
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.100, 1.30
No. of reflections	1401
No. of parameters	121
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.24
Absolute structure	Flack (1983), 378 Friedel pairs
Absolute structure parameter	0.11 (16)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.854 (19)	2.02 (3)	2.823 (5)	156 (5)

Symmetry code: (i) y, −x+1, z+1/4.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058–2077. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2009). Acta Cryst. E65, o2680. Web of Science CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o1522. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P., Nirmala, P. G. & Fuess, H. (2008b). Acta Cryst. E64, o1410. Web of Science CSD CrossRef IUCr Journals Google Scholar
Maren, T. H. (1976). Ann. Rev. Pharmacol Toxicol. 16, 309–327. CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, S. S. & Guillory, J. K. (1972). J. Pharm. Sci. 61, 26–40. CrossRef CAS PubMed Web of Science Google Scholar

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ISSN: 2056-9890

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https://doi.org/10.1107/S1600536810015849

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