N-(4-Hydroxy­phen­yl)-2-(1,1,3-trioxo-2,3-di­hydro-1,2-benzothia­zol-2-yl)­acet­amide

Abha Verma; Edwin D Stevens

doi:10.1107/S1600536809023022

. 2009 Jun 24;65(Pt 7):o1667. doi: 10.1107/S1600536809023022

N-(4-Hydroxyphenyl)-2-(1,1,3-trioxo-2,3-dihydro-1,2-benzothiazol-2-yl)acetamide

Abha Verma ^a, Edwin D Stevens ^a,^*

PMCID: PMC2969438 PMID: 21582927

Abstract

In the title compound, C₁₅H₁₂N₂O₅S, the benzisothiazole group is approximately planar (r.m.s. deviation excluding H atoms and the two O atoms bonded to S = 0.023 Å). The dihedral angle between the benzisothiazole ring and the terminal phenol ring is 84.9 (1)°. In the crystal, molecules are joined by N—H⋯O and O—H⋯O hydrogen bonds, and π-stacking interactions are observed between alternating phenol and benzisothiazole rings [centroid–centroid distances = 3.929 (3) and 3.943 (3) Å].

Related literature

For background literature related to analgesics, see: Slattery et al. (1996 ▶); McGoldrick & Bailie (1997 ▶); Watkins et al. (2006 ▶). For the synthesis and biological activity of the title compound, see: Vaccarino et al. (2007 ▶); González-Martin et al. (1998 ▶); Bazan & Alvarez-Builla (1996a ▶,b ▶). For related structures, see: Arshad et al. (2009a ▶,b ▶,c ▶); Siddiqui et al. (2008a ▶,b ▶; 2007 ▶).

Experimental

Crystal data

C₁₅H₁₂N₂O₅S
M _r = 332.33
Orthorhombic,
a = 16.3588 (10) Å
b = 9.6451 (6) Å
c = 9.9603 (6) Å
V = 1571.56 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 230 K
0.60 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.832, T _max = 0.954
19429 measured reflections
3580 independent reflections
3283 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.084
S = 1.07
3580 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.38 e Å⁻³
Absolute structure: Flack (1983 ▶), 1681 Friedel pairs
Flack parameter: 0.02 (8)

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023022/bi2377sup1.cif

e-65-o1667-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023022/bi2377Isup2.hkl

e-65-o1667-Isup2.hkl^{(175.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 1

Enhanced figure: interactive version of Fig. 2

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯O14ⁱ	0.87 (3)	2.23 (3)	3.078 (3)	165 (3)
O14—H14⋯O9ⁱⁱ	0.82 (3)	1.91 (3)	2.725 (2)	173 (3)

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

Acknowledgments

Helpful discussions with Professor M. L. Trudell, University of New Orleans, are gratefully acknowledged.

supplementary crystallographic information

Comment

Analgesics currently in use have high incidence of adverse reactions and can cause potentially lethal effects like hepatotoxicity and nephrotoxicity (Slattery et al., 1996; McGoldrick & Bailie, 1997; Watkins et al., 2006). A series of compounds bearing the acetaminophen (Tylenol) fragment linked to different lipophilic heterocyclic moieties were synthesized with a view to modulate its pharmacokinetic profile (Bazan & Alvarez-Builla, 1996a,b6; Vaccarino et al., 2007). Of these new derivatives, the title compound (commonly called SCP-1) has a similar profile to that of acetaminophen but with shorter elimination half-life and clearance.

Experimental

The title compound was synthesized following the procedure described by Vaccarino et al. (2007) and colourless needles suitable for X-ray analysis were obtained by recrystallization from an ethanol-water (8:1) mixture.