1-Ethyl-4-[1-(1-phenyl­ethyl­idene)hydrazin-2-yl­idene]-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Muhammad Shafiq; Islam Ullah Khan; Muhammad Nadeem Arshad; Iftikhar Hussain Bukhari; Ejaz

doi:10.1107/S1600536812022982

. 2012 May 31;68(Pt 6):o1927. doi: 10.1107/S1600536812022982

1-Ethyl-4-[1-(1-phenylethylidene)hydrazin-2-ylidene]-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq ^a,^*, Islam Ullah Khan ^b, Muhammad Nadeem Arshad ^c, Iftikhar Hussain Bukhari ^a, Ejaz ^b

PMCID: PMC3379482 PMID: 22719680

Abstract

In the title compound, C₁₈H₁₉N₃O₂S, the thiazine ring adopts an envelope conformation, with the S atom displaced by 0.732 (1) Å from the other atoms of the ring. The phenyl ring is oriented at a dihedral angle of 79.33 (7)° with respect to the fused benzene ring. The conformations about the two double bonds in the R ₂C=N—N=C(CH₃)Ar grouping are Z and E, respectively. In the crystal, inversion dimers linked by pairs of C—H⋯O interactions generate R ₂ ²(8) and R ₂ ²(12) loops, as parts of infinite chains along the a-axis direction.

Related literature

For related structures and further synthetic details, see: Shafiq et al. (2011a ▶,b ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₈H₁₉N₃O₂S
M _r = 341.42
Monoclinic,
a = 9.7278 (3) Å
b = 12.4327 (3) Å
c = 14.2607 (4) Å
β = 100.725 (1)°
V = 1694.60 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.41 × 0.08 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.920, T _max = 0.988
16049 measured reflections
4129 independent reflections
2887 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.151
S = 1.00
4127 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.32 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022982/hb6798sup1.cif

e-68-o1927-sup1.cif^{(24.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022982/hb6798Isup2.hkl

e-68-o1927-Isup2.hkl^{(202.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022982/hb6798Isup3.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
C8—H8A⋯O1ⁱ	0.97	2.43	3.390 (2)	170
C16—H16B⋯O2ⁱⁱ	0.97	2.52	3.481 (2)	171

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

Acknowledgments

MS acknowledges the Higher Education Commission of Pakistan for supporting PhD studies and for the provision of a grant to strengthen the Materials Chemistry Laboratory at GC University Lahore, Pakistan.

supplementary crystallographic information

Comment

As part of our ongoing studies of benzothiazines, we now describe the title compound, which is related to 4-hydrazinylidene-1-ethyl-3H-2λ⁶,1-benzothiazine-2,2-dione and 6-bromo-1-methyl-4-[2-(4-methylbenzylidene) hydrazinylidene]-3H-2λ⁶,1-benzothiazine-2,2-dione. The aromatic and thiazine rings are oriented at dihedral angle of 10.31 (9)° and thiazine ring adopted sofa shape with r. m. s. deviavtion of about 0.2213 (12)° with the maximum deviation of from the S1 (0.3686 (10)Å) & N1 (0.2640 (11)Å). Thiazine ring showes total ring puckering amplitude QT = 0.5430 Å with (θ) = 55.02 ° (π) = 358.2638 ° (Cremer & Pople, 1975). Both the oxygen atoms of SO₂ group are involved in accepting C—H···O type weak intermolecular hydrogen bonding interaction and produce two ring motifs represented as R₂²(8) & R₂²(12) (Table. 1, Fig. 2).

Experimental

4-Hydrazinylidene-1- methyl-3H-2λ⁶,1-benzothiazine-2,2-dione (Shafiq et al., 2011a) was subjected to react with acetophenone according to literature procedure (Shafiq et al., 2011b). The product obtained was then recrystalized in ethylacetate under slow evaporation to obtain suitable crystal for diffraction studies.