1-Ethyl-4-{2-[1-(4-methyl­phen­yl)ethyl­idene]hydrazinyl­idene}-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Muhammad Shafiq; M Nawaz Tahir; William T A Harrison; Tanveer Hussain Bokhari; Muhammad Safder

doi:10.1107/S1600536813000202

. 2013 Jan 9;69(Pt 2):o200. doi: 10.1107/S1600536813000202

1-Ethyl-4-{2-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq ^a,^*, M Nawaz Tahir ^b, William T A Harrison ^c, Tanveer Hussain Bokhari ^a, Muhammad Safder ^a

PMCID: PMC3569261 PMID: 23424484

Abstract

In the title compound, C₁₉H₂₁N₃O₂S, the dihedral angle between the aromatic rings is 6.7 (2)° and the C=N—N=C torsion angle is 178.0 (2)°. The conformation of the thiazine ring is an envelope, with the S atom displaced by 0.802 (2) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.022 Å). In the crystal, molecules are linked by C—H⋯O interactions, generating C(5) chains propagating in [010]. A weak C—H⋯π interaction is also observed.

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq et al. (2011a ▶). For further synthetic details, see: Shafiq et al. (2011b ▶). For a related structure, see: Shafiq et al. (2013 ▶).

Experimental

Crystal data

C₁₉H₂₁N₃O₂S
M _r = 355.45
Monoclinic,
a = 15.9018 (10) Å
b = 7.3716 (4) Å
c = 16.8376 (10) Å
β = 111.644 (3)°
V = 1834.57 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.34 × 0.26 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.937, T _max = 0.955
14168 measured reflections
3597 independent reflections
2598 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.139
S = 1.02
3597 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.45 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: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(20.5KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000202/ld2091sup1.cif

e-69-0o200-sup1.cif^{(20.5KB, cif)}

Click here for additional data file.^{(176.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000202/ld2091Isup2.hkl

e-69-0o200-Isup2.hkl^{(176.4KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000202/ld2091Isup3.cml

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

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

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2ⁱ	0.97	2.50	3.402 (4)	155
C9—H9A⋯Cg3ⁱⁱ	0.97	2.67	3.613 (2)	165

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

Acknowledgments

MS acknowledges the HEC Pakistan for providing a PhD fellowship and the University of Sargodha for the X-ray diffraction facility.

supplementary crystallographic information

Comment

As a part of our ongoing studies of benzothiazine derivatives with potential biactivity (Shafiq et al., 2011a,b), we now describe the synthesis and structure of the title compound, (I).

The dihedral angle between the C1–C6 and C13–C18 aromatic rings is 6.68 (15)° and the C10=N2—N3=C11 torsion angle is 177.98 (19)°. The conformation of the C1/C6/C9/C10/N1/S1 thiazine ring is an envelope, with the S atom displaced by 0.802 (2) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.022 Å). A very similar conformation was observed in a related structure (Shafiq et al., 2013). Atoms C7 and C8 in (I) are displaced from the mean plane of the thiazine ring by -0.416 (5) and 0.704 (6) Å, respectively.

In the crystal, the moelcules are linked by C—H···O interactions (Table 1) to generate C(5) chains propagating in the b axis direction. A weak C—H···π interaction to the C13—C18 ring also occurs (Table 1).

Experimental

4-Hydrazinylidene-1-ethyl-3H-2?6,1-benzothiazine-2,2-dione (Shafiq et al., 2011b) was reacted with para-methyl acetophenone according to literature procedure (Shafiq, et al., 2011a). The product obtained was re-crystallized from ethyl acetate solution to yield yellow prisms.