N-Acetyl-4-(benzene­sulfonamido)benzene­sulfonamide

Muhammad Ashfaq; M Nawaz Tahir; Islam Ullah Khan; Muhammad Nadeem Arshad; Syed Saeed-ul-Hassan

doi:10.1107/S1600536809015876

. 2009 Apr 30;65(Pt 5):o1180. doi: 10.1107/S1600536809015876

N-Acetyl-4-(benzenesulfonamido)benzenesulfonamide

Muhammad Ashfaq ^a, M Nawaz Tahir ^b,^*, Islam Ullah Khan ^a, Muhammad Nadeem Arshad ^a, Syed Saeed-ul-Hassan ^c

PMCID: PMC2977844 PMID: 21583981

Abstract

In the molecule of the title compound, C₁₄H₁₄N₂O₅S₂, the dihedral angle between the aromatic rings is 77.75 (9)°. The acetamide group is planar [maximum deviation = 0.002 (3) Å] and oriented at dihedral angles of 13.49 (21) and 73.94 (10)° with respect to the aromatic rings. An intramolecular C—H⋯O interaction results in the formation of a six-membered ring. In the crystal structure, intermolecular N—H⋯O and C—H⋯O interactions link the molecules into a three-dimensional network, forming R ₂ ²(20) ring motifs.

Related literature

For related structures, see: Chohan et al. (2008 ▶, 2009 ▶); Deng & Mani (2006 ▶); Ellingboe et al. (1992 ▶); Shad et al. (2009 ▶); Tahir et al. (2008 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₄N₂O₅S₂
M _r = 354.39
Monoclinic,
a = 9.9316 (9) Å
b = 9.4828 (8) Å
c = 17.6490 (17) Å
β = 103.169 (5)°
V = 1618.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.909, T _max = 0.940
17674 measured reflections
4034 independent reflections
2423 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.128
S = 1.02
4034 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015876/hk2676sup1.cif

e-65-o1180-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015876/hk2676Isup2.hkl

e-65-o1180-Isup2.hkl^{(193.7KB, 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⋯O5ⁱ	0.86	2.25	2.839 (3)	126
N2—H2N⋯O1ⁱⁱ	0.86	2.14	2.922 (3)	151
C8—H8⋯O2	0.93	2.49	3.116 (3)	125
C9—H9⋯O4ⁱⁱⁱ	0.93	2.60	3.237 (3)	126
C14—H14A⋯O2^iv	0.96	2.56	3.401 (4)	147

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

Acknowledgments

MA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 042-120556-PS2-275).

supplementary crystallographic information

Comment

Sulfonamides have attracted much attention, due to their extensive use in medicine. We have reported the syntheses and crystal structures of sulfonamides, which have the central portion of title compound as common (Chohan et al., 2008, 2009; Shad et al., 2009; Tahir et al., 2008). Similarly, the crystal structure of N-Methyl-N-(2-(methyl(1-methyl-1H-benzimidazol-2-yl)amino)- ethyl)-4-((methylsulfonyl)amino)-benzenesulfonamide (Ellingboe et al., 1992) has been reported, which also has a central portion as in the title compound.

In the molecule of the title compound (Fig 1), rings A (C1-C6) and B (C7-C12) are, of course, planar. The acetamide moiety C (N2/O5/C13/C14) is also planar with a maximum deviation of 0.002 (3) Å for atom C13. The diheadral angles between them are A/B = 77.75 (9), A/C = 13.49 (21) and B/C = 73.94 (10) °. The SO₂ groups are oriented at a dihedral angle of 71.02 (15)°. Intramolecular C-H···O interaction (Table 1) results in the formation of a six-membered ring D (S1/O2/N1/C7/C8/H8) having twisted conformation.

In the crystal structure, intermolecular N-H···O and C-H···O interactions (Table 1) link the molecules into a three-dimensional network forming R₂²(20) ring motifs (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure.

Experimental

The title compound was synthesized according to a literature method (Deng & Mani, 2006). For the preparation of the title compound, phenylglycine (2 g, 5.3 mmol) was dissolved in distilled water, and then benzene sulfonyl chloride (0.93 g, 5.3 mmol) was added. It was stirred at room temperature. During the reaction pH was maintained at 8-9, strictly using Na₂CO₃ (1 M), since HCl was produced as a byproduct, which lowers the pH. The completion of reaction was observed by the consumption of the oily drops of benzene sulfonyl chloride. On completion, pH was adjusted to 2-3 using HCl (2 N). The precipitate formed was filtered, washed with distilled water and recrystalyzed from methanol.