2-Benzoyl-2H-1,4-benzothia­zin-3(4H)-one

Durre Shahwar; M Nawaz Tahir; Naeem Ahmad; Muhammad Asam Raza; Muhammad Akmal Khan

doi:10.1107/S1600536810029582

. 2010 Jul 31;66(Pt 8):o2145. doi: 10.1107/S1600536810029582

2-Benzoyl-2H-1,4-benzothiazin-3(4H)-one

Durre Shahwar ^a, M Nawaz Tahir ^b,^*, Naeem Ahmad ^a, Muhammad Asam Raza ^a, Muhammad Akmal Khan ^a

PMCID: PMC3007413 PMID: 21588432

Abstract

In the title compound, C₁₅H₁₁NO₂S, the dihedral angle between the aromatic rings is 80.35 (7)°. The heterocyclic six-membered ring is not planar: the puckering parameters of this ring are Q = 0.5308 (15) Å, θ = 63.11 (18) and ϕ = 23.5 (2)°. The molecules are linked into inversion dimers with R ₂ ²(8) ring motifs by pairs of N—H⋯O hydrogen bonds. The dimers are interlinked into polymeric sheets extending parallel to the bc plane by C—H⋯O hydrogen bonds, generating R ₂ ¹(7) ring motifs. π–π interactions occur between the benzoyl phenyl rings with centroid–centroid separations of 3.9187 (15) Å.

Related literature

For puckering parameters, see: Cremer & Pople (1975 ▶). For the synthesis and antimicrobial activity of benzimidazole derivatives, see: Güven et al. (2007 ▶): Nofal et al. (2002 ▶). For related structures, see: Beryozkina et al. (2004 ▶): Kumaradhas & Nirmala (1997 ▶): Zhang et al. (2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₁NO₂S
M _r = 269.31
Monoclinic,
a = 9.1323 (3) Å
b = 15.2893 (4) Å
c = 10.5214 (4) Å
β = 114.669 (1)°
V = 1334.99 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.939, T _max = 0.950
10387 measured reflections
2399 independent reflections
2064 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.103
S = 1.04
2399 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.41 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 datablocks global, I. DOI: 10.1107/S1600536810029582/si2280sup1.cif

e-66-o2145-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029582/si2280Isup2.hkl

e-66-o2145-Isup2.hkl^{(115.5KB, hkl)}

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
N1—H1⋯O2ⁱ	0.86	1.98	2.8383 (19)	179
C2—H2⋯O1ⁱⁱ	0.93	2.55	3.453 (2)	165
C8—H8⋯O1ⁱⁱ	0.98	2.36	3.170 (2)	140

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

Acknowledgments

DS is grateful to the Higher Education Commission (Pakistan) for funding of this project and Professor Dr Islam Ullah Khan for providing research facilities at Government College University, Lahore, Pakistan.

supplementary crystallographic information

Comment

Benzothiazin molecules exhibit a broad spectrum of biological activity such as antifungal (Güven et al., 2007) and antibacterial (Nofal et al., 2002) properties. Our group is engaged in preparation and evaluation of biological activities of such type of compounds.

The crystal structures of (II) i.e., 2-(2-(4-bromophenyl)-2-oxoethyl)-4H-benzo-1,4-thiazin-3-one (Beryozkina et al., 2004), (III) 2-(4-chlorobenzoylmethyl)-2H-1,4-benzothiazin-3(4H)-one (Zhang et al., 2008) and (IV) (±)-2-(hydroxy(4-methoxyphenyl)methyl)-2H-1,4-benzothiazin- 3(4H)-one monohydrate (Kumaradhas & Nirmala et al., 1997) have been published which are related to title compound (I), (Fig. 1).

In (I), the benzene rings A (C1—C6) and B (C10—C15) are planar with r. m. s. deviations of 0.0045 and 0.0084 Å, respectively. The dihedral angle between A/B is 80.35 (7)°. The heterocyclic six membered ring C (C8/C9/N1/C10/C11/S1) fused with phenyl ring group B is not planar. The confirmation of this ring may be described by the puckering parameters (Cremer & Pople, 1975): Q = 0.5308 (15) Å, θ = 63.11 (18)°, φ = 23.5 (2)°. The molecules are stabilized in the form of dimers (Fig. 2) due to N—H···O type of H-bondings (Table 1) with R₂²(8) ring motifs (Bernstein et al., 1995). The dimers are interlinked in the form of polymeric sheets extending parallel to bc-plane due to C—H···O type of H-bondings (Table 1, Fig. 2) and complete R₂¹(7) ring motifs. There exist π–π interaction between the centroids of carbonyl containing phenyl rings at a separation of 3.9187 (15) Å [symmetry code: -x, 1 - y, 1 - z].

Experimental

2-Aminothiophenol (0.01 M, 1.08 ml) and ethyl benzoyl acetate (0.01 M, 1.73) were added to 5 ml dimethylsulfoxide. Resulting mixture was refluxed for 1 h and left overnight at room temperature. The separated solid was filtered, washed with petroleum ether and recrystallized with methanol to affoard light yellow plates.