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

Muhammad Shafiq; Islam Ullah Khan; Muhammad Zia-ur-Rehman; Tariq Mahmood; Muhammad Ashfaq; Saeed Ahmad

doi:10.1107/S1600536812025743

. 2012 Jun 13;68(Pt 7):o2100. doi: 10.1107/S1600536812025743

1-Methyl-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 Zia-ur-Rehman ^c, Tariq Mahmood ^d, Muhammad Ashfaq ^e, Saeed Ahmad ^f

PMCID: PMC3393913 PMID: 22798778

Abstract

In the title compound, C₁₇H₁₇N₃O₂S, the phenyl ring is oriented at dihedral angles of 8.5 (2) and 1.17 (14)°, respectively, to the C=N—N plane and the fused aromatic ring. The thiazine ring adopts an envelope conformation with the S atom at the flap. In the crystal, a weak C—H⋯O interaction connects the molecules, forming a helical chain along the a axis.

Related literature

For the synthesis, see: Shafiq et al. (2011 ▶). For related structures, see: Shafiq et al. (2011a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C₁₇H₁₇N₃O₂S
M _r = 327.40
Orthorhombic,
a = 6.6678 (2) Å
b = 12.0783 (6) Å
c = 20.0529 (8) Å
V = 1614.97 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.38 × 0.11 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.923, T _max = 0.985
9111 measured reflections
3830 independent reflections
2819 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.108
S = 0.97
3828 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ▶), 1577 Friedel pairs
Flack parameter: −0.06 (9)

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, New_Global_Publ_Block. DOI: 10.1107/S1600536812025743/is5153sup1.cif

e-68-o2100-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025743/is5153Isup2.hkl

e-68-o2100-Isup2.hkl^{(187.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025743/is5153Isup3.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—H8B⋯O1ⁱ	0.97	2.56	3.420 (3)	148

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Symmetry code: (i) Inline graphic .

Acknowledgments

MS acknowledges the Higher Education Commission of Pakistan for financial support, GC University Lahore, Pakistan for laboratory facilities during his PhD studies and Dr Michael Harmata for guidance during a visit to his laboratory at the University of Missouri, USA.

supplementary crystallographic information

Comment

The present structure is analogue to 1-ethyl-4-[1-(1-phenylethylidene)-hydrazin-2-ylidene]-3,4-dihydro-1H- 2λ⁶,1-benzothiazine-2,2-dione(II) (Shafiq et al., 2012) and related to 4-hydrazinylidene-1-methyl-3H-2λ⁶,1-benzothiazine-2,2-dione (III) (Shafiq, Khan et al., 2011a) and 6-bromo-1-methyl-4-[2- (4-methylbenzylidene)hydrazinylidene]-3H-2λ⁶, 1-benzothiazine-2,2-dione (IV) (Shafiq, Khan et al., 2011b). The structure of molecule looks planer as the plane generated from atoms (C1–C7/C9–C15/N1) showes an r.m.s. deviation of 0.0365 Å, while atoms S1 and C16 show maximum deviations of 0.702 (2) and -0.256 (4) Å, respectively. The fused aromatic ring and the mean plane of the thiazine ring are oriented at a dihedral angle of 9.34 (14)° and thiazine ring adopted sofa shape with an r.m.s. deviation of 0.233 (2)°. Comparison of dihedral angles between the phenyl and fused aromatic rings in I and II [i.e. 1.17 (14) and 79.33 (2)°, respectively] also explain the planarity of title compound. Similarly dihedral angles between the phenyl and thiazine rings in I and II are 9.34 (2) and 69.74 (6)°, respectively. An intermolecular hydrogen bonding interaction of C—H···O type connects the molecule along the a axis and generates a chain structure (Table 1 and Fig. 2). In the group R₂C=N—N=C(CH₃)Ar, the configurations around the two double bonds are Z and E, respectively.

Experimental

In the synthesis of title compound, 4-hydrazinylidene-1- methyl-3H-2λ⁶,1-benzothiazine-2,2-dione (Shafiq, Khan et al., 2011a) was subjected to react with acetophenone according to literature procedure (Shafiq, Zia-ur-Rehman et al., 2011). The product obtained was then recrystallized in ethylacetate under slow evaporation to obtain single crystals suitable for X-ray diffraction.