N-(2-Methyl­phenyl­sulfon­yl)acetamide

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811014218

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1188

doi:10.1107/S1600536811014218

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N-(2-Methylphenylsulfonyl)acetamide

K. Shakuntala,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^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 12 April 2011; accepted 15 April 2011; online 22 April 2011)

In the molecular structure of the title compound, C₉H₁₁NO₃S, the N—H and C=O bonds are anti to each other, while the amide H atom is syn with respect to the ortho-methyl group in the benzene ring. The C—S—N—C torsion angle is −58.2 (2)°, indicating a twist in the molecule. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains along the c axis.

Related literature

For the sulfanilamide moiety in sulfonamide drugs, see: Maren (1976 ). For hydrogen bonding modes of sulfonamides, see: Adsmond & Grant (2001 ). For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2004 ). For background to the structures of N-(substituted phenylsulfonyl)-substituted-amides, see: Gowda et al. (2010 ); Shakuntala et al. (2011 ) and for the oxidative strengths of N-chloro, N-arylsulfonamides, see: Gowda & Kumar (2003 ).

Experimental

Crystal data

C₉H₁₁NO₃S
M_r = 213.25
Tetragonal, P 4₃
a = 7.9804 (5) Å
c = 16.749 (1) Å
V = 1066.69 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 K
0.40 × 0.18 × 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 = 0.895, T_max = 0.967
4245 measured reflections
1944 independent reflections
1690 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.086
S = 1.08
1944 reflections
132 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 824 Friedel pairs
Flack parameter: 0.03 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.86 (2)	1.95 (2)	2.770 (3)	162 (3)
Symmetry code: (i) $[-y+1, x, z-{\script{1\over 4}}]$ .

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: 10.1107/S1600536811014218/tk2737sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014218/tk2737Isup2.hkl

checkCIF report

Comment top

The structures of sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976). The hydrogen bonding preferences of sulfonamides has been investigated (Adsmond & Grant, 2001). The nature and position of the substituents play a significant role on their crystal structures and other aspects of N-(aryl)-amides and N-(aryl)-sulfonamides (Gowda et al., 2003, 2004; Shakuntala et al., 2011). As a part of a study of the effects of substituents on the structures of this class of compounds, the structure of N-(2-methylphenylsulfonyl)-acetamide (I) has been determined (Fig. 1). The conformation of the N—C bond in the C—SO₂—NH—C(O) segment has gauche torsions with respect to the S═O bonds, the torsion angles being C7—N1—S1—O2 = 57.5 (3) ° and C7—N1—S1—O1 = -174.5 (2) °.

The N—H and C═O bonds are anti to each other, similar to that observed in N-(phenylsulfonyl)-acetamide (II) (Gowda et al., 2010) and N-(2-chlorophenylsulfonyl)-acetamide (III) (Shakuntala et al., 2011). Further, the conformation of the amide-H atom is syn to the ortho-methyl group in the benzene ring, similar to that observed between the amide-H atom and the ortho-chloro group in (III). The molecule of (I) is bent at the S-atom with a C—S—N—C torsion angle of -58.2 (2) °, compared to the values of -58.8 (4) ° in (II), and -71.7 (3) and 61.2 (3) ° in the two independent molecules of (III).

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains along the c axis; part of the crystal structure is shown in Fig. 2.

Related literature top

For the sulfanilamide moiety in sulfonamide drugs, see: Maren (1976). For hydrogen bonding modes of sulfonamides, see: Adsmond & Grant (2001). For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2004). For background to the structures of N-(substituted phenylsulfonyl)-substituted-amides, see: Gowda et al. (2010); Shakuntala et al. (2011) and for the oxidative strengths of N-chloro, N-arylsulfonamides, see: Gowda & Kumar (2003).

Experimental top

The title compound was prepared by refluxing 2-methylbenzenesulfonamide (0.10 mole) with an excess of acetyl chloride (0.20 mole) for one 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 re-precipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. Colourless rods of the title compound were obtained from a slow evaporation of its ethanol solution.

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 (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. View of the crystal packing in (I). Hydrogen bonds are shown as dashed lines.

N-(2-Methylphenylsulfonyl)acetamide top

Crystal data top

C₉H₁₁NO₃S	D_x = 1.328 Mg m⁻³
M_r = 213.25	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃	Cell parameters from 1894 reflections
Hall symbol: P 4cw	θ = 2.5–27.8°
a = 7.9804 (5) Å	µ = 0.29 mm⁻¹
c = 16.749 (1) Å	T = 293 K
V = 1066.69 (11) Å³	Prism, colourless
Z = 4	0.40 × 0.18 × 0.12 mm
F(000) = 448

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1944 independent reflections
Radiation source: fine-focus sealed tube	1690 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
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 = −9→5
T_min = 0.895, T_max = 0.967	k = −6→9
4245 measured reflections	l = −17→20

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0453P)² + 0.1227P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.016
1944 reflections	Δρ_max = 0.14 e Å⁻³
132 parameters	Δρ_min = −0.17 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 824 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (9)

Crystal data top

C₉H₁₁NO₃S	Z = 4
M_r = 213.25	Mo Kα radiation
Tetragonal, P4₃	µ = 0.29 mm⁻¹
a = 7.9804 (5) Å	T = 293 K
c = 16.749 (1) Å	0.40 × 0.18 × 0.12 mm
V = 1066.69 (11) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1944 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1690 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.967	R_int = 0.016
4245 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.086	Δρ_max = 0.14 e Å⁻³
S = 1.08	Δρ_min = −0.17 e Å⁻³
1944 reflections	Absolute structure: Flack (1983), 824 Friedel pairs
132 parameters	Absolute structure parameter: 0.03 (9)
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 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	0.0401 (3)	0.5352 (3)	0.16636 (17)	0.0418 (6)
C2	0.0148 (3)	0.3636 (3)	0.15630 (19)	0.0534 (7)
C3	−0.0178 (4)	0.2719 (4)	0.2248 (3)	0.0758 (11)
H3	−0.0359	0.1571	0.2205	0.091*
C4	−0.0243 (5)	0.3456 (5)	0.2992 (2)	0.0844 (12)
H4	−0.0458	0.2805	0.3440	0.101*
C5	0.0008 (4)	0.5134 (5)	0.3071 (2)	0.0730 (10)
H5	−0.0034	0.5631	0.3573	0.088*
C6	0.0326 (4)	0.6095 (4)	0.24026 (19)	0.0571 (7)
H6	0.0490	0.7244	0.2452	0.069*
C7	0.4165 (3)	0.6071 (3)	0.10946 (17)	0.0462 (6)
C8	0.5725 (3)	0.5282 (5)	0.0766 (2)	0.0738 (10)
H8A	0.6102	0.5908	0.0310	0.089*
H8B	0.5489	0.4149	0.0608	0.089*
H8C	0.6582	0.5283	0.1168	0.089*
C9	0.0213 (5)	0.2751 (4)	0.0766 (3)	0.0830 (11)
H9A	0.1276	0.2961	0.0517	0.100*
H9B	−0.0669	0.3162	0.0429	0.100*
H9C	0.0075	0.1568	0.0845	0.100*
N1	0.2818 (3)	0.6051 (3)	0.05903 (12)	0.0413 (5)
H1N	0.278 (3)	0.556 (3)	0.0138 (12)	0.050*
O1	−0.0096 (3)	0.6269 (3)	0.01708 (12)	0.0644 (6)
O2	0.0971 (3)	0.8346 (2)	0.11214 (13)	0.0632 (6)
O3	0.4067 (2)	0.6678 (3)	0.17544 (11)	0.0588 (5)
S1	0.09057 (8)	0.66608 (8)	0.08490 (5)	0.04393 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0313 (12)	0.0414 (14)	0.0526 (15)	0.0022 (11)	0.0085 (11)	−0.0017 (12)
C2	0.0416 (15)	0.0414 (15)	0.077 (2)	0.0004 (12)	0.0128 (14)	−0.0002 (14)
C3	0.068 (2)	0.0495 (18)	0.110 (3)	0.0058 (16)	0.027 (2)	0.017 (2)
C4	0.078 (2)	0.090 (3)	0.085 (3)	0.011 (2)	0.030 (2)	0.033 (2)
C5	0.069 (2)	0.098 (3)	0.0526 (19)	0.0076 (18)	0.0181 (17)	0.0058 (18)
C6	0.0480 (16)	0.0596 (17)	0.0637 (18)	0.0013 (13)	0.0148 (14)	−0.0082 (16)
C7	0.0392 (14)	0.0478 (14)	0.0515 (17)	−0.0071 (11)	−0.0043 (11)	−0.0001 (13)
C8	0.0401 (15)	0.102 (3)	0.080 (2)	0.0051 (15)	0.0006 (17)	−0.012 (2)
C9	0.084 (2)	0.0521 (18)	0.112 (3)	−0.0123 (16)	0.020 (2)	−0.030 (2)
N1	0.0379 (11)	0.0493 (12)	0.0366 (12)	−0.0012 (9)	0.0021 (9)	−0.0061 (9)
O1	0.0510 (12)	0.0821 (16)	0.0601 (14)	0.0057 (10)	−0.0138 (10)	0.0055 (12)
O2	0.0717 (13)	0.0375 (10)	0.0806 (15)	0.0068 (9)	0.0170 (11)	0.0028 (10)
O3	0.0577 (12)	0.0760 (14)	0.0426 (11)	−0.0075 (10)	−0.0091 (9)	−0.0100 (10)
S1	0.0385 (3)	0.0424 (3)	0.0509 (4)	0.0049 (3)	0.0006 (3)	0.0015 (3)

Geometric parameters (Å, º) top

C1—C6	1.374 (4)	C7—N1	1.367 (3)
C1—C2	1.395 (4)	C7—C8	1.500 (4)
C1—S1	1.765 (3)	C8—H8A	0.9600
C2—C3	1.386 (5)	C8—H8B	0.9600
C2—C9	1.511 (5)	C8—H8C	0.9600
C3—C4	1.378 (5)	C9—H9A	0.9600
C3—H3	0.9300	C9—H9B	0.9600
C4—C5	1.361 (6)	C9—H9C	0.9600
C4—H4	0.9300	N1—S1	1.659 (2)
C5—C6	1.380 (5)	N1—H1N	0.855 (17)
C5—H5	0.9300	O1—S1	1.424 (2)
C6—H6	0.9300	O2—S1	1.4213 (19)
C7—O3	1.209 (3)

C6—C1—C2	121.8 (3)	C7—C8—H8A	109.5
C6—C1—S1	116.8 (2)	C7—C8—H8B	109.5
C2—C1—S1	121.4 (2)	H8A—C8—H8B	109.5
C3—C2—C1	116.5 (3)	C7—C8—H8C	109.5
C3—C2—C9	119.4 (3)	H8A—C8—H8C	109.5
C1—C2—C9	124.1 (3)	H8B—C8—H8C	109.5
C4—C3—C2	122.0 (3)	C2—C9—H9A	109.5
C4—C3—H3	119.0	C2—C9—H9B	109.5
C2—C3—H3	119.0	H9A—C9—H9B	109.5
C5—C4—C3	120.2 (3)	C2—C9—H9C	109.5
C5—C4—H4	119.9	H9A—C9—H9C	109.5
C3—C4—H4	119.9	H9B—C9—H9C	109.5
C4—C5—C6	119.6 (3)	C7—N1—S1	123.94 (18)
C4—C5—H5	120.2	C7—N1—H1N	125.3 (19)
C6—C5—H5	120.2	S1—N1—H1N	109.7 (19)
C1—C6—C5	119.9 (3)	O2—S1—O1	119.00 (13)
C1—C6—H6	120.0	O2—S1—N1	109.12 (11)
C5—C6—H6	120.0	O1—S1—N1	104.10 (12)
O3—C7—N1	121.2 (2)	O2—S1—C1	108.68 (13)
O3—C7—C8	123.9 (3)	O1—S1—C1	110.99 (13)
N1—C7—C8	114.9 (3)	N1—S1—C1	103.79 (11)

C6—C1—C2—C3	−0.2 (4)	O3—C7—N1—S1	−6.3 (4)
S1—C1—C2—C3	177.5 (2)	C8—C7—N1—S1	173.3 (2)
C6—C1—C2—C9	180.0 (3)	C7—N1—S1—O2	57.5 (3)
S1—C1—C2—C9	−2.3 (4)	C7—N1—S1—O1	−174.5 (2)
C1—C2—C3—C4	−0.3 (5)	C7—N1—S1—C1	−58.2 (2)
C9—C2—C3—C4	179.6 (3)	C6—C1—S1—O2	−6.2 (3)
C2—C3—C4—C5	0.3 (6)	C2—C1—S1—O2	176.0 (2)
C3—C4—C5—C6	0.1 (5)	C6—C1—S1—O1	−138.9 (2)
C2—C1—C6—C5	0.6 (4)	C2—C1—S1—O1	43.3 (2)
S1—C1—C6—C5	−177.3 (2)	C6—C1—S1—N1	109.8 (2)
C4—C5—C6—C1	−0.5 (5)	C2—C1—S1—N1	−68.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.86 (2)	1.95 (2)	2.770 (3)	162 (3)

Symmetry code: (i) −y+1, x, z−1/4.

Experimental details

Crystal data
Chemical formula	C₉H₁₁NO₃S
M_r	213.25
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	293
a, c (Å)	7.9804 (5), 16.749 (1)
V (Å³)	1066.69 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.40 × 0.18 × 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	0.895, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	4245, 1944, 1690
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.086, 1.08
No. of reflections	1944
No. of parameters	132
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)	0.14, −0.17
Absolute structure	Flack (1983), 824 Friedel pairs
Absolute structure parameter	0.03 (9)

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	0.855 (17)	1.946 (18)	2.770 (3)	162 (3)

Symmetry code: (i) −y+1, x, z−1/4.

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

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