(±)-N-(3-Hydr­oxy-1,2-diphenyl­prop­yl)-4-methyl­benzene­sulfonamide

Sok Teng Tong; David Barker; Ka Wai Choi; Peter D W Boyd; Margaret A Brimble

doi:10.1107/S1600536808028948

. 2008 Sep 24;64(Pt 10):o1990. doi: 10.1107/S1600536808028948

(±)-N-(3-Hydroxy-1,2-diphenylpropyl)-4-methylbenzenesulfonamide

Sok Teng Tong ^a, David Barker ^a,^*, Ka Wai Choi ^a, Peter D W Boyd ^a, Margaret A Brimble ^a

PMCID: PMC2959308 PMID: 21201189

Abstract

In the title compound, C₂₂H₂₃NO₃S, the relative stereochemistry of the two stereogenic centres is anti with respect to the H atoms. The molecular packing of the crystal shows a double-strand arrangement, consisting of one strand of (S*,S*) enantiomers and one strand of (R*,R*) enantiomers. Both strands lie parallel to each other along the a axis. Each strand is made up of dimers in which the molecules are connected to each other via an intermolecular O—H⋯O hydrogen bond between the hydroxyl groups and an O—H⋯π interaction with the aromatic ring. These units are then connected to neighbouring dimers via N—H⋯O hydrogen bonds and C—H⋯O interactions. Intramolecular C—H⋯O interactions are also observed.

Related literature

For a similar organocatalytic α-oxdiation of ketones, see: Engqvist et al. (2005 ▶). For a related structure, see: Chinnakali et al. (2007 ▶).

Experimental

Crystal data

C₂₂H₂₃NO₃S
M _r = 381.47
Monoclinic,
a = 39.4702 (16) Å
b = 5.4270 (2) Å
c = 17.4287 (7) Å
β = 91.028 (2)°
V = 3732.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 90 (2) K
0.4 × 0.16 × 0.14 mm

Data collection

Bruker SMART diffractometer with APEXII CCD detector
Absorption correction: none
22582 measured reflections
4478 independent reflections
3763 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.193
S = 1.13
4478 reflections
245 parameters
15 restraints
H-atom parameters constrained
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Data collection: SMART (Siemens, 1995 ▶); cell refinement: SAINT (Siemens, 1995 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028948/pv2094sup1.cif

e-64-o1990-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028948/pv2094Isup2.hkl

e-64-o1990-Isup2.hkl^{(215KB, 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—H1⋯O1ⁱ	0.86	2.45	3.122 (3)	136
O3—H3A⋯O3ⁱⁱ	0.85	2.06	2.910 (5)	180
C4—H4⋯O1	0.93	2.55	2.909 (4)	104
C8—H8⋯O1	0.98	2.61	2.958 (3)	101
C1—H1A⋯O2ⁱⁱⁱ	0.96	2.63	3.557 (4)	161
C1—H1B⋯O2^iv	0.96	2.74	3.552 (4)	142
O3—H3B⋯C16ⁱⁱ	0.86	2.67	3.489 (4)	160.1
O3—H3B⋯C17ⁱⁱ	0.86	2.85	3.499 (4)	133.7

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

Acknowledgments

The authors thank Tania Groutso for the data collection. The awards of an International Doctoral Scholarship from the University of Auckland and a New Zealand International Doctoral Research Scholarship from Education New Zealand (to STT) are greatly appreciated.

supplementary crystallographic information

Comment

The title racemic sulfonamide was obtained unintentionally as a product from the study of the organocatalytic α-oxidation of phenylacetaldehyde catalysed by (S)-proline. The relative stereochemistry of the two stereogenic centres was established by X-ray crystallography as anti with respect to the H atoms of C8 and C15 (Fig. 1).

The molecular packing of the crystal shows a double strand arrangement, which consists of one strand of (8S*,15S*) enantiomers and one strand of (8R*,15R*) enantiomers. Both strands lie parallel to each other along the a axis and a number of hydrogen bonds has been observed throughtout the crystal lattice.

Each strand is made up of homodimeric units in which the sulfonamide molecules are connected to each other by intermolecular hydrogen bonds between the hydroxyl groups (O3—H3···O3) as well as the O—H···π interaction with the aromatic ring. The dimer is, in turn, linked to the next dimer along the strand via non-conventional hydrogen bonds (C1—H1A···O2—S1 and C1—H1B···O2—S1). Finally, neighbouring strand of the same stereochemistry are connected to each other via conventional (N1—H1···O1—S1) and non-conventional (C1—H1A···O2—S1 and C1—H1B···O2—S1) hydrogen bonds (Fig. 2).

Non-conventional intramolecular hydrogen interactions (C4—H4···O1—S1 and C8—H8···O1—S1) are also observed with a distance of 2.55 and 2.61 Å between the hydrogen and the acceptor oxygen (Table 1).

Experimental

To a solution of 3-phenyl-2-tosyl-1,2-oxaziridine (551 mg, 2.00 mmol) in distilled THF (8 ml) was added under ambient atmosphere (S)-proline (69.1 mg, 0.600 mmol). After 5 minutes, phenylacetaldehyde (0.450 ml, 4.00 mmol) was added. After 1 h, sodium borohydride (151 mg, 4.00 mmol) was added to the mixture at 273 K and the mixture was stirred overnight. The mixture was then poured onto a biphasic mixture of HCl (1 mol l^-1) and EtOAc (1:1, 8 ml) at 273 K and vigorously stirred for 10 minutes. The organic phase was separated and the aqueous phase was extracted with EtOAc (8 ml x 4). The combined organic extracts were washed with brine, dried over MgSO₄ and concentrated in vacuo to afford a yellow oil. Purification by flash chromatography using hexane–EtOAc (2:1 to 1:1) as eluent yielded the title sulfonamide as a white solid (6%). Recrystallization of the title sulfonamide in hexane–CH₂Cl₂ (4:1) afforded colourless needles.