Methyl 4-hy­droxy-1,1-dioxo-2-(2-phenyl­eth­yl)-2H-1λ6,2-benzothia­zine-3-carboxyl­ate

Muhammad Nadeem Arshad; Islam Ullah Khan; Muhammad Zia-ur-Rehman; Muhammad Danish; K Travis Holman

doi:10.1107/S160053681104966X

. 2011 Nov 25;67(Pt 12):o3445. doi: 10.1107/S160053681104966X

Methyl 4-hydroxy-1,1-dioxo-2-(2-phenylethyl)-2H-1λ⁶,2-benzothiazine-3-carboxylate

Muhammad Nadeem Arshad ^a,^*, Islam Ullah Khan ^b, Muhammad Zia-ur-Rehman ^c, Muhammad Danish ^a, K Travis Holman ^d

PMCID: PMC3239077 PMID: 22199925

Abstract

In the title compound, C₁₈H₁₇NO₅S, the thiazine ring adopts a half-chair conformation and the dihedral angle between the aromatic rings is 79.41 (6)°. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by weak C—H⋯O interactions resulting in infinite sheets along the b and c axes.

Related literature

For related structures, see: Arshad et al. (2011a ▶); Ahmad et al. (2010 ▶); Khalid et al. (2010 ▶). For further synthetic details, see: Arshad et al. (2011b ▶). For graph-set notation, see: Bernstein, et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₈H₁₇NO₅S
M _r = 359.39
Monoclinic,
a = 9.018 (2) Å
b = 19.026 (4) Å
c = 10.193 (2) Å
β = 106.441 (3)°
V = 1677.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.37 × 0.23 × 0.08 mm

Data collection

Bruker SMART 1K diffractometer with a Bruker APEXII CCD detector
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.922, T _max = 0.982
19773 measured reflections
4066 independent reflections
2735 reflections with I > 2σ(I)
R _int = 0.094

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.116
S = 1.01
4066 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 ▶); software used to prepare material for publication: X-SEED (Barbour, 2001 ▶), WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104966X/hb6520sup1.cif

e-67-o3445-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104966X/hb6520Isup2.hkl

e-67-o3445-Isup2.hkl^{(195.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681104966X/hb6520Isup3.cml

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
C2—H2⋯O3ⁱ	0.95	2.55	3.391 (3)	147
C17—H17⋯O2ⁱⁱ	0.95	2.53	3.205 (3)	128
C18—H18⋯O4ⁱⁱⁱ	0.95	2.49	3.308 (3)	145
O1—H1⋯O4	0.92 (3)	1.74 (3)	2.583 (2)	152 (3)

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

Acknowledgments

MNA acknowledges the HEC for providing a fellowship under the International Research Support Initiative Program (IRSIP).

supplementary crystallographic information

Comment

Benzothiazines molecules are well explored for their crystallographic studies (Arshad et al. 2011a), (Ahmad et al. 2010), (Khalid et al. 2010).

In the title compound, the nitrogen atom of methyl-4-hydroxy-2H-1, 2-benzothiazine-3-carboxylate 1,1-dioxide was alkylated with phenylethyl group. The thiazine ring (with root mean square deviation = 0.210Å) is oriented at dihedral angle of 13.12 (11)° with respect to the aromatic ring (C1—C6) and the S1 & N1 atoms showed deviations from the least square plane by 0.3121 (10)Å and -0.3310 (12)Å, respectively. The thiazine ring adopts a half chair conformation with puckering amplitude Q = 0.5160 (16)Å θ = 63.6 (2)°, φ = 26.3 (2)° (Cremer & Pople, 1975). The phenyl ring (C13—C17) is oriented at dihedral angle of 79.41 (6)° and 66.53 (5)° with respect to the aromatic (C1—C6) and thiazine rings respectively. The intramolecular O–H···O interaction observed and generates an almost planer S(6) ring (Bernstein, et al., 1995) with the r.m.s deviaton of 0.0131Å and produces dihedral angles of 16.02 (33)° & 15.87 (32)° with respect to the thiazine and aromatic (C1—C6) rings respectively.

Weak hydrogen bonding interactions of C—H···O type connect the molecules. The interaction C2—H2···O3 resulted in the formation of dimers which are further linked along b and c axes (Fig.2. Tab.1).

Experimental

The title compound was synthesised according to literature procedure (Arshad et al. 2011b) and crystalized in methanol under slow evaporation to yield colourless blocks.