N,N′-{[Ethane-1,2-diylbis(­oxy)]bis­(ethane-2,1-di­yl)}bis­(4-methyl­benzene­sulfonamide)

Nassir N Al-Mohammed; Yatimah Alias; Zanariah Abdullah; Hamid Khaledi

doi:10.1107/S1600536812024324

. 2012 Jun 2;68(Pt 7):o1983. doi: 10.1107/S1600536812024324

N,N′-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4-methylbenzenesulfonamide)

Nassir N Al-Mohammed ^a, Yatimah Alias ^a, Zanariah Abdullah ^a, Hamid Khaledi ^a,^*

PMCID: PMC3393259 PMID: 22807816

Abstract

The asymmetric unit of the title compound, C₂₀H₂₈N₂O₆S₂, contains one half-molecule, related to the other half by a twofold rotation axis. The two aromatic rings of the molecule make a dihedral angle of 50.91 (7)°. The O—CH₂—CH₂—O and N—CH₂—CH₂—O fragments both adopt gauche conformations, with torsion angles of 76.0 (4) and 70.4 (3)°, respectively. In the crystal, adjacent molecules are linked through N—H⋯O hydrogen bonds into chains along the a-axis direction. The chains are further connected via C—H⋯O interactions into a two-dimensional supramolecular network in the ac plane.

Related literature

For similar structures, see: Polyakova et al. (1990 ▶); Ding et al. (2003 ▶).

Experimental

Crystal data

C₂₀H₂₈N₂O₆S₂
M _r = 456.56
Monoclinic,
a = 11.135 (7) Å
b = 9.220 (6) Å
c = 21.452 (15) Å
β = 93.680 (12)°
V = 2198 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.23 × 0.14 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.938, T _max = 0.989
5135 measured reflections
1983 independent reflections
1558 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.150
S = 1.03
1983 reflections
140 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024324/pv2551sup1.cif

e-68-o1983-sup1.cif^{(19KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024324/pv2551Isup2.hkl

e-68-o1983-Isup2.hkl^{(97.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812024324/pv2551Isup3.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⋯O2ⁱ	0.82 (2)	2.14 (2)	2.944 (3)	171 (3)
C6—H6⋯O1ⁱⁱ	0.93	2.56	3.311 (4)	138

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

Acknowledgments

The authors thank the University of Malaya for funding this study (HIR MOHE (Fakulti) F0004–21001).

supplementary crystallographic information

Comment

The title compound (Fig. 1) was obtained through the condensation reaction of 1,8-diamino-3,6-dioxaoctane with p-toluenesulfonyl chloride. A twofold rotation axis passes through the mid-point of C10—C10' bond (symmetry code: ' = -x + 2, y, -z + 3/2), the asymmetric unit therefore comprises one half of the molecule. The two symmetry related aromatic rings in the molecule make a dihedral angle of 50.91 (7)°. Similar to what was observed in a related structure (Polyakova et al., 1990), the O—CH₂—CH₂—O and N—CH₂—CH₂—O fragments adopt the gauche conformations with torsion angles of 76.0 (4) and 70.4 (3)° respectively. The S—O bond distances [1.423 (2) and 1.433 (2) Å] and S—N bond distance [1.608 (2) Å] are comparable to the values found in the literature (Ding et al., 2003; Polyakova et al., 1990). The crystal packing of the molecule shows layers in the ac plane formed by N—H···O and C—H···O interactions (Table 1, Fig. 2)

Experimental

A solution of p-toluenesulfonyl chloride (2.83 g, 1.48 mmol) in dry dichloromethane (25 ml) was added drop wise to a dichloromethane solution (25 ml) of 1,8-diamino-3,6-dioxaoctane (1 g, 0.675 mmol) and triethylamine (2.34 ml, 1.69 mmol) at 273 K. The mixture was stirred at room temperature overnight, washed with water and saturated solution of NaHCO₃ (3 x 10 ml) and dried over MgSO₄. The organic layer was evaporated and the residue was dissolved in methanol. The colorless crystals of the title compound were obtained through slow evaporation of the methanolic solution at room temperature (m.p. = 361–363 K).