N-(3-Amino­bicyclo­[2.2.1]heptan-2-yl)-4-methyl­benzene­sulfonamide

Alaa A-M Abdel-Aziz; Adel S El-Azab; Magda A El-Sherbeny; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812025421

. 2012 Jun 13;68(Pt 7):o2032. doi: 10.1107/S1600536812025421

N-(3-Aminobicyclo[2.2.1]heptan-2-yl)-4-methylbenzenesulfonamide

Alaa A-M Abdel-Aziz ^a,^b,^‡, Adel S El-Azab ^a,^c, Magda A El-Sherbeny ^b, Seik Weng Ng ^d,^e, Edward R T Tiekink ^d,^*

PMCID: PMC3393301 PMID: 22807858

Abstract

In the title compound, C₁₄H₂₀N₂O₂S, the sulfonamide O atoms lie to one side of the benzene ring and the aminobicycloheptanyl to the other side [C_ar—S—N—C torsion angle = −57.93 (11)°; ar = aromatic]. An intramolecular N—H⋯N hydrogen bond is formed. In the crystal, a supramolecular chain is formed along the b axis via N—H⋯O and N—H⋯N hydrogen bonds.

Related literature

For chiral ligands in asymmetric catalytic reactions, see: Seo et al. (2001 ▶); Abdel-Aziz et al. (2004 ▶); Matsunaga et al. (2005 ▶); Yamakuchi et al. (2005 ▶).

Experimental

Crystal data

C₁₄H₂₀N₂O₂S
M _r = 280.38
Monoclinic,
a = 10.1715 (2) Å
b = 6.1169 (1) Å
c = 11.5150 (3) Å
β = 110.332 (2)°
V = 671.80 (2) Å³
Z = 2
Cu Kα radiation
μ = 2.14 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.566, T _max = 0.814
4721 measured reflections
2750 independent reflections
2731 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.024
wR(F ²) = 0.066
S = 1.03
2750 reflections
185 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ▶), 1217 Friedel pairs
Flack parameter: −0.001 (10)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025421/lh5485sup1.cif

e-68-o2032-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025421/lh5485Isup2.hkl

e-68-o2032-Isup2.hkl^{(135KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025421/lh5485Isup3.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—H1n⋯O1ⁱ	0.88 (1)	2.20 (1)	2.976 (2)	148 (2)
N1—H2n⋯N2	0.87 (1)	2.39 (2)	2.752 (2)	105 (2)
N2—H3n⋯N1ⁱ	0.89 (1)	2.04 (1)	2.907 (2)	166 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors extend their appreciation to the Research Center of Pharmacy, King Saud University, for funding this work. They also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM·C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

The title compound (I) was synthesized in the context of the development of chiral ligands for asymmetric catalytic reactions (Seo et al., 2001; Abdel-Aziz et al., 2004; Matsunaga et al., 2005; Yamakuchi et al. 2005).

In (I), Fig. 1, the two S-bound O atoms lie to one side of the adjacent benzene ring with the O1 and O2 atoms lying -0.466 (1) and -0.771 (1) Å out of the plane, respectively, and the aminobicycloheptanyl residue lying to the other side, the C8—S1—N2—C2 torsion being -57.93 (11)°. An intramolecular N—H···N hydrogen bond is noted, Table 1.

Molecules are connected into a supramolecular chain along the b axis via N—H···O and N—H···N hydrogen bonds that generate 12-membered {···HNC₂NH···OSNC₂N} synthons, Fig. 2 and Table 1. The chains pack into a three-dimensional architecture without specific interactions between them, Fig. 3.

Experimental

To the mixture of 2-imidazolidinone (2.0 ml), water (2 ml), ethanol (6 ml) and Ba(OH)₂.8H₂O (20 ml) were added. This was heated at 413 K in a glass sealed tube for 24 h. The solvents were evaporated and the precipitate extracted three times with chloroform (10 ml × 3). The organic extract was dried and crystallized from ethanol to afford the title compound.