N-Butyl-4-hydr­oxy-2-methyl-2H-1,2-benzothia­zine-3-carboxamide 1,1-dioxide

Matloob Ahmad; Hamid Latif Siddiqui; Saeed Ahmad; Syed Umar Farooq; Masood Parvez

doi:10.1107/S160053680801670X

. 2008 Jun 7;64(Pt 7):o1213–o1214. doi: 10.1107/S160053680801670X

N-Butyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Matloob Ahmad ^a, Hamid Latif Siddiqui ^a,^*, Saeed Ahmad ^b, Syed Umar Farooq ^a, Masood Parvez ^c

PMCID: PMC2961640 PMID: 21202852

Abstract

The title compound, C₁₄H₁₈N₂O₄S, contains hydrogen-bonded dimeric pairs of molecules arranged around inversion centers, forming 14-membered rings with an R ₂ ²(14) motif. The structure is stabilized by extensive intramolecular interactions. The thiazine ring adopts a half-chair conformation, with the S and N atoms displaced by −0.485 (3) and 0.296 (3) Å, respectively, from the plane formed by the remaining atoms of the ring.

Related literature

For related literature, see: Ahmad, Siddiqui, Ahmad et al. (2008 ▶); Ahmad, Siddiqui, Zia-ur-Rehman et al. (2008 ▶); Bernstein et al. (1994 ▶); Gupta et al. (1993 ▶, 2002 ▶); Kojić-Prodić & Rużić-Toroš (1982 ▶); Lombardino (1971 ▶); Lombardino & Wiseman (1972 ▶); Rehman et al. (2005 ▶, 2006 ▶); Sianesi et al. (1973 ▶); Siddiqui et al. (2008 ▶); Zinnes et al. (1982 ▶); Drebushchak et al. (2006 ▶).

Experimental

Crystal data

C₁₄H₁₈N₂O₄S
M _r = 310.36
Monoclinic,
a = 10.233 (2) Å
b = 14.780 (4) Å
c = 10.365 (5) Å
β = 108.79 (2)°
V = 1484.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 (2) K
0.14 × 0.12 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.968, T _max = 0.986
12380 measured reflections
3405 independent reflections
2646 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.100
S = 1.03
3405 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: HKL DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S160053680801670X/bh2176sup1.cif

e-64-o1213-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801670X/bh2176Isup2.hkl

e-64-o1213-Isup2.hkl^{(163.6KB, 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
O3—H3O⋯O4	0.88 (2)	1.76 (2)	2.572 (2)	153 (2)
N2—H2N⋯O2ⁱ	0.87 (2)	2.21 (2)	3.052 (2)	161 (2)
N2—H2N⋯N1	0.87 (2)	2.34 (2)	2.753 (2)	109 (2)
C9—H9B⋯O2	0.98	2.49	2.864 (2)	102

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Several benzothiazine derivatives like piroxicam, sudoxicam (Lombardino & Wiseman, 1972; Rehman et al., 2005) and isoxicam (Zinnes et al., 1982) have been reported in the literature to be potential anti-inflammatory agents. Some of the derivatives of benzothiazines are found to be analgesic (Gupta et al., 2002), anti-cancer (Gupta et al., 1993) and exhibitors of central nervous system activity (Sianesi et al., 1973). We have reported anti-bacterial activities (Rehman et al., 2006) of a series of 1,2-benzothiazines. In continuation of our work on 1,2-benzothiazines 1,1-dioxides (Ahmad, Siddiqui, Ahmad, Irfan Ashiq & Tizzard, 2008; Ahmad, Siddiqui, Zia-ur-Rehman, Ashiq & Tizzard, 2008), we report in this paper the crystal structure of the title compound, (I), which was patented for Pfizer Inc. (Lombardino, 1971).

The structure of (I), (Fig. 1), contains dimeric pairs of molecules lying about inversion centers resulting from N2—H2N···O2 hydrogen bonds (Fig. 2). The 14-membered rings thus formed represent R₂²(14) motif in the graph set notation (Bernstein et al., 1994). Similar hydrogen-bonded dimers have been reported in structures related to the title compound (Siddiqui et al., 2008; Drebushchak et al., 2006; Kojić-Prodić & Rużić-Toroš, 1982). The structure is stabilized by extensive intramolecular interactions (Fig. 1 and Table 1). The thiazine ring in (I) adopts a half-chair conformation with atoms S1 and N1 displaced by -0.485 (3) and 0.296 (3) Å, respectively, from the plane formed by the remaining atoms of the ring.

Experimental

Methyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (1.0 g, 3.72 mmoles) was dissolved in n-butyl amine (5 ml) in a test tube. The mixture was placed at room temperature for 7 days. Crystals of (I) suitable for crystallographic analysis were found, which were washed with MeOH.