N-[4-(Ethyl­sulfamo­yl)phen­yl]acetamide

Jeveria Rehman; Ejaz; Islam Ullah Khan; William T A Harrison; Sidra Farid

doi:10.1107/S1600536811033472

. 2011 Aug 27;67(Pt 9):o2455. doi: 10.1107/S1600536811033472

N-[4-(Ethylsulfamoyl)phenyl]acetamide

Jeveria Rehman ^a, Ejaz ^a, Islam Ullah Khan ^a,^*, William T A Harrison ^b, Sidra Farid ^a

PMCID: PMC3200875 PMID: 22059023

Abstract

The title compound, C₁₀H₁₄N₂O₃S, crystallized with two molecules (A and B) in the asymmetric unit. The terminal methyl group of the ethylsulfonamide moiety in molecule B is disordered over two sets of sites with an occupancy ratio of 0.61 (1):0.39 (1). Both molecules have L-shaped conformations. In molecule A, the dihedral angles between the benzene ring and its ethylsulfonamide and methylamide substituents are 83.5 (3) and 13.34 (18)°, respectively. Equivalent values for molecule B are 87.9 (3) and 6.32 (16)°, respectively. The C—S—N—C torsion angles are 66.5 (3)° for A and −64.4 (3)° for B, indicating similar twists about the S—N bonds, but in opposite senses. In the crystal, the A molecules are linked by pairs of N_s—H⋯O (s = sulfonamide) hydrogen bonds, generating inversion dimers containing R ₂ ²(8) rings, while the B molecules are linked by N_s—H⋯O hydrogen bonds into C(10) [100] chains. Finally, N_a—H⋯O (a = amide) hydrogen bonds link the A-molecule dimers and B-molecule chains into a three-dimensional network.

Related literature

For related structures, see: Hou et al. (2009 ▶); Khan et al. (2011 ▶); Rehman et al. (2011 ▶).

Experimental

Crystal data

C₁₀H₁₄N₂O₃S
M _r = 242.29
Triclinic,
a = 8.2766 (3) Å
b = 12.1728 (4) Å
c = 13.5041 (4) Å
α = 70.130 (2)°
β = 73.935 (2)°
γ = 71.517 (2)°
V = 1191.56 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.40 × 0.35 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.901, T _max = 0.949
18017 measured reflections
4310 independent reflections
2701 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.117
S = 1.04
4310 reflections
317 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033472/su2301sup1.cif

e-67-o2455-sup1.cif^{(24.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033472/su2301Isup2.hkl

e-67-o2455-Isup2.hkl^{(211.2KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.79 (3)	2.13 (3)	2.914 (3)	173 (3)
N2—H2N⋯O4ⁱⁱ	0.80 (2)	2.21 (2)	3.006 (3)	169 (3)
N3—H3N⋯O6ⁱⁱⁱ	0.83 (3)	2.03 (3)	2.854 (3)	173 (3)
N4—H4N⋯O3^iv	0.75 (2)	2.21 (2)	2.960 (3)	174 (3)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

IUK thanks the Higher Education Commission of Pakistan for financial support under the project to strengthen the Materials Chemistry Laboratory at GCUL.

supplementary crystallographic information

Comment

As part of our ongoing structural studies of sulfonamides (Khan et al., 2011; Rehman et al., 2011), the synthesis and crystal structure of the title compound are reported on herein. The related stucture of N-(p-acetamidobenzenesulfonyl)glycine has been described previously (Hou et al., 2009).

The title compound, C₁₀H₁₄N₂O₃S, crystallized with two molecules (A and B) in the asymmetric unit (Fig. 1). The -CH₃ group of the ethylsulfonamide moiety (atom C20) in molecule B is disordered over two positions [C20a and C20b with occupancies 0.61 (1):0.39 (1)]. Both molecules have L-shaped conformations in which the ethylsulfonamide group is roughly perpendicular to the benzene ring, but the methyl-amide group is almost coplanar with the same ring. In molecule A the dihedral angles between the benzene ring (C1-C6) and the ethylsulfonamide (S1,N1,C9,C10) and methylamide (N2,C7,O3,C8) moieties are 83.5 (3) and 13.34 (18)°, respectively. The equivalent values for molecule B [benzene ring (C11-C16); ethylsulfonamide (S2,N3,C19,C20a); methylamide (N4,C17,O6,C18)] are 87.9 (3) and 6.32 (16)°, respectively. The C—S—N—C torsion angles are 66.5 (3)° for A and -64.4 (3)° for B, indicating similar twists about the S—N bonds in the two molecules, but in opposite senses. Similar twists about the equivalent S—N bonds were seen in 4-methyl-N-(4-aminophenyl)benzenesulfonamide (Rehman et al., 2011).

In the crystal, the A molecules are linked by pairs of N_s—H···O (s = sulfonamide) hydrogen bonds to generate inversion dimers containing R²₂(8) rings (Fig. 2), while the B molecules are linked by N_s—H···O hydrogen bonds into C(10) [100] chains (Fig. 3). Finally, N_a—H···O (a = amide) hydrogen bonds link the dimers and chains into a three-dimensional network - see Table 1 for details of the hydrogen bonding.

Experimental

Ethyl amine (1 mmol, 0.0654 ml) was dissolved in distilled water (20 ml) in a round bottom flask (100 ml) and 4-(acetylamino)benzenesulfonyl chloride (1 mmol, 0.23367 g) was added with stirring at room temperature while keeping the pH of solution between 8.0–9.0 with sodium carbonate solution (3%). After 4 h, the white precipitate formed was filtered, washed with distilled water and dried. Colourless block-like crystals of the title compound were grown from methanol by slow evaporation.