N-[3-(Benzene­sulfonamido)­prop­yl]benzene­sulfonamide

Tahir Ali Sheikh; Islam Ullah Khan; William T A Harrison; Ejaz

doi:10.1107/S1600536811020150

. 2011 Jun 18;67(Pt 7):o1737. doi: 10.1107/S1600536811020150

N-[3-(Benzenesulfonamido)propyl]benzenesulfonamide

Tahir Ali Sheikh ^a, Islam Ullah Khan ^a,^*, William T A Harrison ^b, Ejaz ^a

PMCID: PMC3151767 PMID: 21837125

Abstract

In the title compound, C₁₅H₁₈N₂O₄S₂, the dihedral angle between the aromatic rings is 71.8 (2)°. The conformation of the central N—C—C—C—N fragment is gauche–gauche [torsion angles = 72.5 (5) and 65.7 (5)°]. Both N atoms adopt pyramidal geometries. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating (001) sheets, and weak C—H⋯O interactions consolidate the packing.

Related literature

For a related structure, see: Linden & Bienz (1999 ▶).

Experimental

Crystal data

C₁₅H₁₈N₂O₄S₂
M _r = 354.43
Orthorhombic,
a = 9.2650 (13) Å
b = 16.402 (2) Å
c = 22.740 (3) Å
V = 3455.5 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
13896 measured reflections
3393 independent reflections
1607 reflections with I > 2σ(I)
R _int = 0.091

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.181
S = 1.03
3393 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.35 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/S1600536811020150/om2431sup1.cif

e-67-o1737-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020150/om2431Isup2.hkl

e-67-o1737-Isup2.hkl^{(166.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020150/om2431Isup3.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⋯O4ⁱ	0.82 (4)	2.15 (5)	2.954 (6)	164 (4)
N2—H2⋯O3ⁱⁱ	0.74 (4)	2.15 (4)	2.836 (4)	154 (5)
C9—H9B⋯O4ⁱⁱⁱ	0.97	2.51	3.430 (5)	158
C13—H13⋯O1^iv	0.93	2.42	3.276 (8)	153

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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

The title compound, (I), complements N-{4-[(benzenesulfonyl)amino]butyl}benzenesulfonamide, C₁₆H₂₀N₂O₄S₂ (Linden & Bienz, 1999), (II), with a propyl chain in (I) replacing the butyl chain in (II).

In (I) (Fig. 1), the dihedral angle between the aromatic rings is 71.8 (2)°. The conformation of the central N—C—C—C—N chain linking the two S atoms can be described as gauche–gauche in terms of the N1—C7—C8—C9 and C7—C8—C9—N2 torsion angles of 72.5 (5) and 65.7 (5)°, respectively. Both N atoms in (I) are clearly in pyramidal coordination geometries, implying that the lone pairs on the N atoms are not conjugated with their adjacent benzene sulfonyl groups. A similar situation was observed in (II).

In the crystal of (I), the molecules are linked by N—H···O hydrogen bonds (Table 1). Considered separately, the N1 bond leads to [010] C(8) chains and the N2 bond generates [100] C(4) chains. Both the acceptor O atoms are part of the same (atom S2) sulfonyl group: it is perhaps notable that these O atoms have significantly smaller U_eq values that the O atoms in the other (atom S1) sulfonyl group that do not accept a hydrogen bond. Overall, (001) sheets arise from the N—H···O hydrogen bonds in (I) and weak C—H···O links consolidate the packing.

The complete molecule of (II) is generated by inversion symmetry and therefore the conformation of the central alkyl chain is all-trans and the dihedral angle between the aromatic rings is constrained to be zero by symmetry.

Experimental

A mixture of 1,3-diaminoprpoane (0.0067 mol, 0.561 ml) and benzene sulfonyl chloride (0.0135 mol, 1.72 ml), was stirred in 15 ml of distilled water, while maintaining the pH of the reaction mixture at 9 using 3% sodium carbonate. The progress of the reaction was checked by TLC. On completion, the precipitate obtained was filtered, washed with water and finally dried. Colourless blocks of (I) were grown from methanol by slow evaporation.