4-(1H-Benzimidazol-2-ylmeth­yl)-2H-1,4-benzothia­zin-3(4H)-one

Hoong-Kun Fun; Mohd Mustaqim Rosli; Janardhana Gowda; A M A Khader; B Kalluraya

doi:10.1107/S1600536810019367

. 2010 May 29;66(Pt 6):o1495. doi: 10.1107/S1600536810019367

4-(1H-Benzimidazol-2-ylmethyl)-2H-1,4-benzothiazin-3(4H)-one

Hoong-Kun Fun ^a,^*,^‡, Mohd Mustaqim Rosli ^a, Janardhana Gowda ^b, A M A Khader ^b, B Kalluraya ^b

PMCID: PMC2979569 PMID: 21579557

Abstract

In the title compound, C₁₆H₁₃N₃OS, the thiomorpholine ring exists in a screw boat conformation. The angle between the benzimidazole ring system and the benzene ring fused to the thiazine ring is 67.22 (6)°. In the crystal, molecules form infinite chains along the a axis via intermolecular N—H⋯N interactions. C—H⋯π interactions also contribute to the stability of the crystal structure.

Related literature

For the biological activity of molecules containing 1H-benzimidazole, see: Sridhar & Ramesh (2001 ▶); Guven et al. (2007 ▶); Nofal et al. (2002 ▶); Pedini et al. (1994 ▶). For a related structure, see: Fun et al. (2009 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₁₃N₃OS
M _r = 295.35
Orthorhombic,
a = 9.4498 (8) Å
b = 17.0223 (16) Å
c = 17.4454 (16) Å
V = 2806.2 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.50 × 0.20 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.893, T _max = 0.969
16727 measured reflections
4075 independent reflections
3185 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.119
S = 1.03
4075 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019367/wn2387sup1.cif

e-66-o1495-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019367/wn2387Isup2.hkl

e-66-o1495-Isup2.hkl^{(199.8KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2ⁱ	0.859 (19)	1.926 (19)	2.7800 (15)	173 (2)
C12—H12A⋯Cg1ⁱⁱ	0.93	2.97	3.6736 (16)	134
C3—H3A⋯Cg2ⁱⁱⁱ	0.93	2.61	3.4750 (17)	155

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

Acknowledgments

FHK and MMR thank Universiti Sains Malaysia for the Research University Golden Goose grant (No. 1001/PFIZIK/811012).

supplementary crystallographic information

Comment

A number of molecules containing the 1H-benzimidazole nucleus exhibit a broad spectrum of biological activity, including anti-inflammatory (Sridhar et al., 2001), antifungal (Guven et al., 2007), antibacterial (Nofal et al., 2002) and anthelmintic (Pedini et al., 1994) properties. With these results in mind, we have paid particular attention to the preparation of derivatives of 1H-benzimidazole and we report here the crystal structure of the title compound, a 1H-benzimidazole derivative containing 2H-1,4-benzothiazin-3(4H)-one.

The bond lengths and angles are within normal ranges. The thiomorpholine ring (C1, C6-C8, N3, S1) adopts a screw boat confirmation with puckering parameters (Cremer & Pople, 1975) being Q = 0.6563 (13) Å; θ = 66.76 (12)° and φ = 334.16 (14)°. The angle between the benzimidazole ring system and the benzene ring fused to the thiazine ring is 67.22 (6)°.

The intermolecular interaction N1—H1N1···N2 links the molecules to form infinite chains along the a-axis. The crystal structure is further stabilized by C—H···π interactions involving the C1-C6 (Cg1) and C11-C16 (Cg2) benzene rings (Table 1).

Experimental

A mixture of 2-(3-oxo-2,3-dihydro-4H-1,4-benzothiazin-4-yl)acetic acid (3.3 mmol) (Fun et al., 2009) and o-phenylenediamine (2.2 mmol) was heated at 140 °C under solvent-free conditions for 3 h and completion of the reaction was checked by TLC. The reaction mixture was cooled to room temperature and the solid product was washed with a saturated solution of sodium bicarbonate to yield 4-(1H-benzimidazol-2-ylmethyl)-2H-1,4-benzothiazin-3(4H)-one as a red solid. Single crystals suitable for X-ray analysis were obtained by crystallization from absolute ethanol under slow evaporation (M.p. 493 K).