N-[2-(Amino­carbon­yl)phen­yl]-4-hydr­oxy-2-methyl-2H-1,2-benzothia­zine-3-carboxamide 1,1-dioxide

Muhammad Nadeem Arshad; Muhammad Zia-ur-Rehman; Islam Ullah Khan

doi:10.1107/S1600536809038951

. 2009 Sep 30;65(Pt 10):o2596. doi: 10.1107/S1600536809038951

N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Muhammad Nadeem Arshad ^a, Muhammad Zia-ur-Rehman ^b,^*, Islam Ullah Khan ^a

PMCID: PMC2970422 PMID: 21578031

Abstract

In the title compound, C₁₇H₁₅N₃O₅S, the thiazine ring adopts a distorted half-chair conformation. The molecular structure is stabilized by intramolecular N—H⋯O, N—H⋯N and O—H⋯O hydrogen bonding. Pairs of molecules are bound together as centrosymmetric dimers through N—H⋯O hydrogen bonds.

Related literature

For the synthesis of related molecules, see: Braun (1923 ▶); Ahmad et al. (2008 ▶); Zia-ur-Rehman et al. (2005 ▶, 2009 ▶). For the biological activity of 1,2-benzothiazine 1,1-dioxides, see: Bihovsky et al. (2004 ▶); Turck et al. (1996 ▶); Zia-ur-Rehman et al. (2006 ▶). For similar molecules, see: Kojić-Prodić & Rużić-Toroš (1982 ▶); Siddiqui et al. (2009 ▶); Weast et al. (1984 ▶); Zia-ur-Rehman et al. (2007 ▶).

Experimental

Crystal data

C₁₇H₁₅N₃O₅S
M _r = 373.38
Monoclinic,
a = 8.1377 (6) Å
b = 7.0515 (6) Å
c = 29.069 (2) Å
β = 96.502 (3)°
V = 1657.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.39 × 0.25 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.915, T _max = 0.975
16109 measured reflections
3753 independent reflections
3011 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.087
wR(F ²) = 0.213
S = 1.09
3753 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: APEX2 (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: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038951/bt5073sup1.cif

e-65-o2596-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038951/bt5073Isup2.hkl

e-65-o2596-Isup2.hkl^{(184KB, 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
O1—H1⋯O4	0.82	1.85	2.569 (5)	145
N2—H2⋯O5	0.86	1.92	2.607 (5)	136
N2—H2⋯N1	0.86	2.28	2.728 (5)	113
N3—H3A⋯O5ⁱ	0.86	2.22	2.941 (6)	141

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the PCSIR Laboratories Complex, Lahore, for the provision of facilities necessary to complete this work.

supplementary crystallographic information

Comment

Owing to the verstaile applications of 1,2-benzothiazine 1,1-dioxides, considerable attention has been given to their synthesis since their very first synthesis (Braun, 1923). Among these, Piroxicam (Zia-ur-Rehman et al., 2005), and Meloxicam (Turck et al., 1996) are familiar for their analgesic action and are being used world wide as non-steroidal anti-inflammatory drugs (NSAIDs). Some of the 3,4-dihydro-1,2-benzothiazine-3-carboxylate 1,1-dioxide α-ketomide and P(2)—P(3) peptide mimetic aldehyde compounds act as potent calpain I inhibitors (Bihovsky et al., 2004) while 1,2-benzothiazin-3-yl-quinazolin-4(3H)-ones possess anti-bacterial properties (Zia-ur-Rehman et al., 2006).

In continuation of our work on the synthesis (Zia-ur-Rehman et al., 2006, biological activity (Zia-ur-Rehman et al., 2009) and crystal structures (Zia-ur-Rehman et al., 2007; Ahmad et al., 2008, Siddiqui et al., 2009) of various 1,2-benzothiazine-1,1-dioxides, we herein report the crystal structure of the title compound (I) (Scheme and figure 1). Like its already reported dimethylsulfoxide solvate analogue (Zia-ur-Rehman et al., 2007), thiazine ring involving two double bonds, exhibits sofa conformation; with S1/C1/C2/C7 relatively planar and N1 showing significant departure from plane due to its pyramidal geometry. The enolic hydrogen on O1 is involved in intramolecular hydrogen bonding [O1—H1···O4] with the carbonyl oxygen at C9 giving rise to a six-membered hydrogen bond ring (Table 1). Atom H2 forms hydrogen bonds with both N1 and O5 giving rise to five and six-membered hydrogen bond rings respectively. The C1—S1 [1.755 Å] bond is shorter than a normal C—S single bond (1.81–2.55 Å) (Weast et al., 1984) due to partial double bond character and is in agreement with similar molecules (Kojić-Prodić & Rużić-Toroš, 1982). Each molecule is centrosymmetrically linked to its adjacent one forming a dimer through intermolecular [N—H3B···O5] hydrogen bonds (Fig. 2).

Experimental

N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine- 3-carboxamide 1,1-dioxide was synthesized according to a literature method (Zia-ur-Rehman et al., 2006). Suitable crystals were obtained by dissoving the compound in chloroform followed by slow evaporation at room temperature.The compound was dissolved in a mixture of methanol and DMSO (80:20 v/v) at room temperature. Crystals were obtained by slow evaporation and dried under high vacuum.