cis-N-(2-Hydroxy­cyclo­hexyl)-p-toluene­sulfonamide

Mohamed I Fadlalla; Holger B Friedrich; Glenn E M Maguire; Muhammad D Bala

doi:10.1107/S1600536810002151

. 2010 Jan 27;66(Pt 2):o463. doi: 10.1107/S1600536810002151

cis-N-(2-Hydroxycyclohexyl)-p-toluenesulfonamide

Mohamed I Fadlalla ^a, Holger B Friedrich ^a, Glenn E M Maguire ^a, Muhammad D Bala ^a,^*

PMCID: PMC2979744 PMID: 21579875

Abstract

There are two symmetry-independent molecules in the asymmetric unit of the title compound, C₁₃H₁₉NO₃S. The cyclohexane rings in the two molecules adopt chair configurations. The hydroxy and amino groups on the cyclohexane ring assume axial and equatorial orientations, respectively, with respect to the plane of the ring. The crystal structure is stabilized by two intermolecular N—H⋯O and O—H⋯O hydrogen bonds from the two symmetry-independent molecules.

Related literature

For related structures of β-amino alcohols, see: Bergmeier (2000 ▶); Krzemiński & Wojtczak (2005 ▶). For related structures of tosylamino compounds, see: Coote et al. (2008 ▶); Liu et al. (2005 ▶); Chinnakali et al. (2007 ▶); Nan & Xing (2006 ▶). For the synthesis of the title compound, see: Naiker et al. (2008 ▶).

Experimental

Crystal data

C₁₃H₁₉NO₃S
M _r = 269.35
Triclinic,
a = 6.3031 (1) Å
b = 12.8355 (2) Å
c = 17.5367 (3) Å
α = 106.645 (1)°
β = 93.971 (1)°
γ = 100.047 (1)°
V = 1327.75 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.51 × 0.31 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
18458 measured reflections
6423 independent reflections
4837 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.111
S = 1.07
6423 reflections
343 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002151/lx2131sup1.cif

e-66-0o463-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002151/lx2131Isup2.hkl

e-66-0o463-Isup2.hkl^{(308KB, 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⋯O6ⁱ	0.83 (2)	2.00 (2)	2.8255 (17)	175.0 (18)
N2—H2N⋯O3ⁱⁱ	0.82 (2)	2.00 (2)	2.8155 (18)	173.1 (19)
O3—H3O⋯O5ⁱⁱⁱ	0.83 (2)	1.93 (2)	2.7489 (15)	171 (2)
O6—H6O⋯O2^iv	0.83 (2)	1.98 (2)	2.8001 (15)	169 (2)

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

Acknowledgments

We wish to thank Dr Manuel Fernandes (University of the Witwatersrand) for the data collection, and the NRF, THRIP and the University of KwaZulu-Natal for financial support.

supplementary crystallographic information

Comment

Molecules containing a β-amino alcohol system have been used as precursors for the synthesis of chiral ligands, aziridine and biologically active compounds (Bergmeier, 2000; Krzemiński & Wojtczak, 2005). As a part of study on this family of compounds, we report the crystal structure of the title compound (l) (Fig. 1).

The geometry of the benzenesulfonamide unit in (I) agrees with that for related structures (Chinnakali et al. 2007; Nan & Xing, 2006). The cyclohexane rings in the two molecules adopt the chair configuration. The hydroxy and amino groups on the cyclohexane ring respectively assume axial and equatorial orientations with respect to the plane of the ring. The crystal packing (Fig. 2) is stabilized by intermolecular N—H···O and O—H···O hydrogen bonds from the two neighbouring symmetry-independent molecules (Table 1).

Experimental

The synthesis of the title compound was carried out using a modified literature method (Naiker et al. 2008) using a catalytic process. To a nitrogen saturated Schlenk tube, toluene (6 ml), water (172 µl) chloroamine-T (0.21 g, 0.956 mmol), cyclohexene (0.478 mmol) and catalyst (0.03 g) were added in that order. After the complete conversion of the starting material the catalyst was gravity filtered. The reaction mixture was washed with 15 ml of sodium sulfite (1 g in 15 ml of de-ionized water), followed by 15 ml of ethyl acetate. Then the aqueous layer was separated from the organic layer and washed further with 3 × 15 ml of ethyl acetate. The solvent was removed in vacuo, and the crude product was purified using preparative high pressure liquid chromatography to yield the title compound as a white solid. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetonitrile/water (1:1 v/v) at room temperature. (mp; 414–416 K) Spectroscopic analysis: ¹³C NMR (400 MHz, CDCl₃, δ, p.p.m): = 19.76 (s, 1 C), 21.54 (s, 2 C), 27.98 (s, 1 C), 31.46(s, 1 C), 55.10 (s, 1 C), 68.76 (s, 1 C), 126.97 (s, 2 C), 129.74 (s, 2 C), 137.98(s, 1 C), 143.39 (s, 143.39).. MS m/z –[fragment]–(%): 291.8 (M + Na⁺) calculated = 291.8 for C₁₃H₁₉NO₃SNa⁺.

FT–IR (cm^-1): = 3414(m), (OH), 3137(m), (NH), 2938(w), 2849(w), 1598(m), (ar), 1059(m), (S=O).