N,N′-(Ethane-1,2-di­yl)dibenzene­sulfonamide

Mohammad T M Al-Dajani; Jamal Talaat; Nornisah Mohamed; Madhukar Hemamalini; Hoong-Kun Fun

doi:10.1107/S1600536811030157

. 2011 Aug 2;67(Pt 9):o2214. doi: 10.1107/S1600536811030157

N,N′-(Ethane-1,2-diyl)dibenzenesulfonamide

Mohammad T M Al-Dajani ^a, Jamal Talaat ^b, Nornisah Mohamed ^a, Madhukar Hemamalini ^c, Hoong-Kun Fun ^c,^*,^‡

PMCID: PMC3200692 PMID: 22064806

Abstract

In the title compound, C₁₄H₁₆N₂O₄S₂, the dihedral angle between the terminal phenyl rings is 77.07 (13)°. The geometries around the S atoms are distorted tetrahedral, with O—S—O angles of 120.66 (12) and 119.44 (11)°. In the crystal, molecules are stacked in columns along the a axis via intermolecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For biological activities and applications of sulfonamide derivatives, see: Misra et al. (1982 ▶); Maren (1976 ▶); Li et al. (1995 ▶); Yoshino et al. (1992 ▶). For related structures, see: Basak et al. (1982 ▶); Cotton & Stokley (1970 ▶).

Experimental

Crystal data

C₁₄H₁₆N₂O₄S₂
M _r = 340.41
Monoclinic,
a = 5.2115 (4) Å
b = 16.6905 (13) Å
c = 17.8750 (14) Å
β = 93.187 (2)°
V = 1552.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.46 × 0.08 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.852, T _max = 0.975
14604 measured reflections
3545 independent reflections
2628 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.119
S = 1.04
3545 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.33 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030157/is2755sup1.cif

e-67-o2214-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030157/is2755Isup2.hkl

e-67-o2214-Isup2.hkl^{(170.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811030157/is2755Isup3.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—H1N1⋯O2ⁱ	0.73 (3)	2.40 (3)	3.053 (3)	149 (3)
N2—H1N2⋯O3ⁱ	0.83 (3)	2.15 (3)	2.924 (3)	157 (2)
C10—H10A⋯O1ⁱⁱ	0.93	2.57	3.294 (3)	135

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

Acknowledgments

NM gratefully acknowledges funding from Universiti Sains Malaysia (USM) under the Research University Grant No. 1001/PFARMASI/821142. HKF and MH thank the Malaysian government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

supplementary crystallographic information

Comment

Sulfonamide is found in a number of synthetic as well as natural compounds. These molecules exhibit antibacterial (Misra et al., 1982), insulin-releasing (Maren, 1976), anti-inflammatory (Li et al., 1995) and antitumor (Yoshino et al., 1992) activities. An X-ray study of the title compound was undertaken in order to determine its crystal and molecular structure owing to the biological importance of its analogues. The molecular structure is shown in Fig. 1.

The molecule is bent at the N atoms with C9-S2-N2-C8 and C7-N1-S1-C6 torsion angles of 58.48 (18) and 72.6 (2)°, respectively. The geometries around the sulfonamide S atoms are in a slightly distorted tetrahedral configuration, similar to that observed in other reported structures (Basak et al., 1982). The maximum and minimum values of the angles around S are 121.62 (17) and 105.92 (11)°, respectively. This deviation can be attributed to the non-bonded interactions involving the S–O bonds, resulting in a structure with less steric interference (Cotton & Stokley, 1970) and the varied steric bulk of the substituents. The dihedral angle between the terminal phenyl C1–C6 and C9–C14 rings is 77.07 (13)°.

In the crystal structure, the molecules are connected via intermolecular N1—H1N1···O2, N2—H1N2···O3 and C10—H10A···O1 hydrogen bonds (Table 1) forming one-dimensional supramolecular chains along the a axis (Fig. 2).

Experimental

In a round bottom flask, 25ml from toluene was mixed with benzenesulfonyl chloride (0.02 mol, 3.5 g) with stirring. Drops of ethylenediamine (0.01 mol, 0.5 g ) was added and the mixture was refluxed for 30 min. The yellow gum formed was dissolved in hot water and sodium bicarbonate was added. The yellow precipitate formed was dissolved in methanol at 60 °C, yielding colourless crystals.