4-[2-(Anthracen-9-yl­methyl­idene)hydrazinyl­idene]-3-chloro-1-methyl-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Muhammad Shafiq; M Nawaz Tahir; Islam Ullah Khan; Tanveer Hussain Bokhari; Muhammad Nadeem Asghar

doi:10.1107/S1600536812021642

. 2012 May 19;68(Pt 6):o1788. doi: 10.1107/S1600536812021642

4-[2-(Anthracen-9-ylmethylidene)hydrazinylidene]-3-chloro-1-methyl-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq ^a, M Nawaz Tahir ^b,^*, Islam Ullah Khan ^c, Tanveer Hussain Bokhari ^a, Muhammad Nadeem Asghar ^d

PMCID: PMC3379367 PMID: 22719565

Abstract

In the title compound, C₂₄H₁₈ClN₃O₂S, the dihedral angle between the benzene ring and the anthracene ring system is 41.10 (8)°. The thiazine ring has a half-chair conformation and the Cl atom is in an axial orientation. In the crystal, molecules are linked by C—H⋯O interactions, generating C(8) chains along [100]. A C—H⋯N short contact occurs in the molecule, generating an S(6) ring.

Related literature

For a related structure and references to further synthetic details, see: Shafiq et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). graphic file with name e-68-o1788-scheme1.jpg

Experimental

Crystal data

C₂₄H₁₈ClN₃O₂S
M _r = 447.92
Monoclinic,
a = 8.5133 (4) Å
b = 19.8999 (8) Å
c = 12.7849 (6) Å
β = 105.026 (2)°
V = 2091.88 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.930, T _max = 0.960
16154 measured reflections
3788 independent reflections
2827 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.136
S = 1.04
3788 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021642/hb6779sup1.cif

e-68-o1788-sup1.cif^{(29.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021642/hb6779Isup2.hkl

e-68-o1788-Isup2.hkl^{(181.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812021642/hb6779Isup3.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
C3—H3⋯O2ⁱ	0.93	2.59	3.370 (4)	142
C22—H22⋯N3	0.93	2.29	2.913 (4)	123

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

As part of our ongoing studies of thiazine derivatives (Shafiq et al., 2012), we now describe the structure of the title compound, (I), (Fig. 1).

In (I), the benzene ring A (C1—C6) and anthracene group B (C10—C23) are almost planar with r. m. s. deviation of 0.0090 and 0.0144 Å, respectively. The dihedral angle between A/B is 41.10 (8)°. The central group C (N2/N3/C9) is of course planar. The dihedral angle between A/C and B/C is 13.63 (26) and 27.48 (26)°, respectively. The thiazine ring D (C1/C6/C7/C8/S1/N1) is in the half-chair form, with the maximum puckering amplitude (Cremer & Pople, 1975), Q = 0.578 (2) Å. There exist S(6) ring motif (Bernstein et al., 1995) due to H-bonding of C—H···N type (Table 1, Fig. 1). The molecules form C(8) chains extending along the a-axis due to H-bonding of C—H···O type (Table 1, Fig. 2).

Experimental

Schiff base derivative of (4Z)-4-hydrazinylidene-1-methyl-3,4-dihydro -1H-2,1-benzothiazine 2,2-dioxide and anthracene-9-carbaldehyde was prepared using the method reported previously (Shafiq et al. 2012). The chlorination of the schiff base was undertaken using N-chloro succinimide and dibenzoylperoxide (Shafiq et al., 2012). The crude product of (I) was re-crystallized in ethyl acetate to get orange prisms.