N-(4-Sulfamoylphen­yl)acetamide

Abdullah M Asiri; Hassan M Faidallah; Tariq R Sobahi; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812011701

. 2012 Mar 24;68(Pt 4):o1155. doi: 10.1107/S1600536812011701

N-(4-Sulfamoylphenyl)acetamide

Abdullah M Asiri ^a,^b,^‡, Hassan M Faidallah ^a, Tariq R Sobahi ^a, Seik Weng Ng ^c,^a, Edward R T Tiekink ^c,^*

PMCID: PMC3344098 PMID: 22606101

Abstract

In the title compound, C₈H₁₀N₂O₃S, the dihedral angle between the acetamide group and the benzene ring is 15.59 (12)° and the amino group is close to being perpendicular to the benzene ring [N—S—C_ar—C_ar (ar = aromatic) torsion angle = 109.4 (2)°]. In the crystal, molecules are linked into supramolecular tubes parallel to [001] by amine–amide N—H⋯O interactions and these are connected into the three-dimensional architecture by amide–sulfonamide N—H⋯O hydrogen bonds. The crystal studied was a racemic twin.

Related literature

For background to the biological applications of related sulfonamides, see: Croitoru et al. (2004 ▶); Dogruer et al. (2010 ▶). For related structures, see: Asiri et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C₈H₁₀N₂O₃S
M _r = 214.24
Tetragonal,
a = 15.2631 (4) Å
c = 8.0571 (4) Å
V = 1877.00 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 100 K
0.40 × 0.05 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.880, T _max = 0.984
3827 measured reflections
1862 independent reflections
1698 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.079
S = 1.02
1862 reflections
140 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ▶), 625 Friedel pairs
Flack parameter: 0.48 (9)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011701/hb6682sup1.cif

e-68-o1155-sup1.cif^{(15KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011701/hb6682Isup2.hkl

e-68-o1155-Isup2.hkl^{(91.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812011701/hb6682Isup3.cml

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—H1⋯O3ⁱ	0.88 (1)	2.08 (1)	2.935 (3)	163 (3)
N1—H2⋯O3ⁱⁱ	0.89 (1)	2.04 (1)	2.929 (3)	178 (3)
N2—H3⋯O1ⁱⁱⁱ	0.88 (1)	2.34 (2)	3.156 (3)	155 (2)

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

Acknowledgments

The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing the research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

The crystal and molecular structure of N-(4-sulfamoylphenyl)acetamide (I) is reported herein in continuation of on-going structural studies of sulfonamide derivatives (Asiri et al., 2011; Asiri et al., 2012), of interest owing to their biological activity, for example, to selectively inhibit COX–2 (Croitoru et al., 2004) and as they exhibit anti-microbial and anti-fungal activities (Dogruer et al. 2010).

In (I), Fig. 1. the amide residue is twisted out of the plane of the benzene ring to which it is attached as seen in the value of the C7—N2—C4—C3 torsion angle of -166.2 (2)°, and the amino group occupies a position perpendicular to the benzene ring with the N1—S1—C1—C2 torsion angle being 109.4 (2)°.

Each of the N—H hydrogen atoms forms a hydrogen bond to an oxygen atom with the amide-O3 atom being bifurcated, Table 1. The amino-H atoms bridge the amide-O atoms to generate supramolecular tubes along the c axis. These are connected into the three-dimensional architecture by amide-H···O(sulfonamide) hydrogen bonds, Fig. 2 and Table 1.

Experimental

2-Acetyl chloride (0.784 g, 25 mmol) in pyridine (5 ml) was slowly added to a solution of sulfanilamide (2.00 g, 11 mmol) in pyridine (20 ml) and the reaction mixture was stirred at 258 K for 4 h under anhydrous conditions. After warming the solution to room temperature, the pyridine was removed in vacuo and the resulting white solid dissolved in ethyl acetate. The organic extract was washed with 3 M hydrochloric acid (30 ml) then with saturated sodium bicarbonate solution (30 ml) and finally with brine. Drying over magnesium sulfate and evaporation yielded a white solid which was recrystallized from ethanol to give the title compound as colourless prisms. Yield: 74%. M.pt: 491–492 K.