N-(4-Acetyl­phen­yl)-4-meth­oxy­benzene­sulfonamide

Thawanrat Kobkeatthawin; Suchada Chantrapromma; C S Chidan Kumar; Hoong-Kun Fun

doi:10.1107/S1600536813029875

. 2013 Nov 6;69(Pt 12):o1750–o1751. doi: 10.1107/S1600536813029875

N-(4-Acetylphenyl)-4-methoxybenzenesulfonamide

Thawanrat Kobkeatthawin ^a, Suchada Chantrapromma ^a,^*,^‡, C S Chidan Kumar ^b, Hoong-Kun Fun ^b,^§

PMCID: PMC3885030 PMID: 24454205

Abstract

The title compound, C₁₅H₁₅NO₄S, was obtained by the condensation of 4-aminoacetophenone and 4-methoxybenzenesulfonyl chloride. The dihedral angle between the benzene rings is 86.56 (9)° and the molecule has an approximate V-shaped conformation. The C atom of the methoxy group is roughly coplanar with its attached ring [deviation = 0.177 (3) Å], as is the methyl C atom of the acetyl group with its ring [deviation = 0.065 (2) Å]. An intramolecular C—H⋯O interaction generates an S(6) ring. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the molecules into [010] chains. Weak C—H⋯π interactions are also observed.

Related literature

For related structures, see: Li et al. (2006 ▶); Xu et al. (2005 ▶). For background to and applications of sulfonamides, see: Alsughayer et al. (2011 ▶); Dragostin et al. (2013 ▶); graphic file with name e-69-o1750-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₅NO₄S
M _r = 305.35
Monoclinic,
a = 12.8220 (3) Å
b = 8.2709 (2) Å
c = 14.6165 (4) Å
β = 112.841 (1)°
V = 1428.52 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 K
0.48 × 0.44 × 0.33 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.894, T _max = 0.924
15571 measured reflections
4120 independent reflections
2593 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.135
S = 1.04
4120 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813029875/hb7153sup1.cif

e-69-o1750-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029875/hb7153Isup2.hkl

e-69-o1750-Isup2.hkl^{(201.9KB, hkl)}

Click here for additional data file.^{(5.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813029875/hb7153Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3ⁱ	0.85 (2)	2.05 (2)	2.896 (2)	172.3 (19)
C8—H8A⋯O2	0.93	2.38	3.030 (2)	127
C9—H9A⋯O1ⁱⁱ	0.93	2.53	3.459 (2)	174
C14—H14A⋯Cg1ⁱ	0.96	2.83	3.630 (3)	141
C14—H14C⋯Cg2ⁱⁱⁱ	0.96	2.83	3.529 (2)	130
C15—H15C⋯Cg1^iv	0.96	2.99	3.804 (3)	144

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

Acknowledgments

Financial support from the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0137/2554) is gratefully acknowledged. CSCK thanks the Universiti Sains Malaysia for a postdoctoral research fellowship. The authors extend their appreciation to Prince of Songkla University and the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

supplementary crystallographic information

1. Comment

Sulfonamides containing an –SO₂NH– group can be found in many pharmacologically active compounds: recent reports have described antibacterial (Alsughayer et al., 2011) and antioxidant (Dragostin et al., 2013) behaviour. As part of our ongoing research in this field, the title compound (I), a 4-methoxybenzene-sulfonamide derivative, was synthesized for being used as starting material for various syntheses. Herein the crystal structure of (I) is reported.

Figure 1 shows the molecular structure of (I), C₁₅H₁₅NO₄S, suggesting a V-shaped conformation (Fig. 2). The benzene rings make the dihedral angle of 86.56 (9)°. The methoxy group is almost co-planar with its attached benzene ring with the deviation of 0.0310 (2) Å for the eight non H atoms (C1–C6/O4/C15) and the torsion angle C15–O4–C4–C5 = -2.2 (3)°. The amide group and acetyl substituent also lie in almost the same plane with the bound benzene ring with the deviation of 0.0220 (2) Å for the ten non H atoms (C7–C14/N1/O3) and the torsion angles of C11–C10–C13–O3 = -177.28 (18)° and C11–C10–C13–C14 = 2.6 (3)°. The dihedral angle between these two planes [C1–C6/O4/C15 and C7–C14/N1/O3] is 88.38 (7)° (Fig. 2). An intramolecular C8—H8A···O2 weak interaction generates an S(6) ring (Fig. 1) Bond distances of (I) are comparable with those in related structures (Li et al., 2006 and Xu et al., 2005).

In the crystal (Fig. 3), the molecules are linked by N—H···O hydrogen bonds and C—H···O weak interactions (Table 1) into chains along [010]. Weak C—H···π interactions are also observed (Table 1).

2. Experimental

The title compound was synthesized by condensation of 4-aminoacetophenone (0.40 g, 3 mmol) and 4-methoxybenzenesulfonyl chloride in CH₂Cl₂ (30 ml) in the presence of pyridine. The reaction mixture was refluxed for 24 hr at 40 °C and monitored with TLC for the completion of the reaction. Water was then added and the concoction was extracted with CH₂Cl₂. The solvent was evaporated under reduced pressure to yield the resulting solid of the title compound (yield 68%). Yellow blocks of (I) were recrystalized from acetone:CH₃OH solution (1:1 v/v) by slow evaporation of the solvent at room temperature after several days, Mp. 448–449 K.