7H-[1,2]Benzothia­zolo[3,2-b]quinazoline 5,5-dioxide

Ponmudisettu Narayanan; Subramani Karthikeyan; Panayancheri Coleppa Srinivasan; Krishnan Sethusankar

doi:10.1107/S1600536812040871

. 2012 Oct 6;68(Pt 11):o3082. doi: 10.1107/S1600536812040871

7H-[1,2]Benzothiazolo[3,2-b]quinazoline 5,5-dioxide

Ponmudisettu Narayanan ^a, Subramani Karthikeyan ^a, Panayancheri Coleppa Srinivasan ^a, Krishnan Sethusankar ^a,^*

PMCID: PMC3515187 PMID: 23284414

Abstract

In the title compound, C₁₄H₁₀N₂O₂S, the benzothiazole and quinazoline ring systems are essentially planar with maximum deviations of 0.0127 (16) and 0.1588 (15) Å, respectively, and make a dihedral angleof 3.02 (5)°, which shows that the entire molecule is almost planar. The O atoms deviate from the benzothiazole ring system by 1.2231 (14) and −1.1989 (15) Å. The crystal packing features non–classical C—H⋯O hydrogen bonds and is further consolidated by π–π interactions [centroid–centroid distances = 3.7568 (8) and 3.8848 (9) Å].

Related literature

For the uses and biological importance of benzothiazole and quinazoline derivatives, see: Schwartz et al. (1992 ▶); Wolfe et al. (1990 ▶); Tereshima et al. (1995 ▶). For related structures, see: Khan et al. (2012 ▶); Grundt et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₁₀N₂O₂S
M _r = 270.31
Orthorhombic,
a = 7.9389 (2) Å
b = 13.1460 (4) Å
c = 22.7952 (7) Å
V = 2379.02 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.922, T _max = 0.947
21710 measured reflections
2328 independent reflections
1981 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.122
S = 1.06
2328 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(21.8KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040871/rk2382sup1.cif

e-68-o3082-sup1.cif^{(21.8KB, cif)}

Click here for additional data file.^{(112.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040871/rk2382Isup2.hkl

e-68-o3082-Isup2.hkl^{(112.2KB, hkl)}

Click here for additional data file.^{(4.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812040871/rk2382Isup3.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
C2—H2⋯O1ⁱ	0.93	2.43	3.275 (2)	150

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection. They also thank the University Grant Commission (UGC) for funding the minor project [Ref. No. F. MRP–3640/11 (SERO–UGC)] under which this work has been carried out.

supplementary crystallographic information

Comment

Saccharin belongs to a class of cyclic sulfonamides and this is used as an artificial sweetener for a longtime. The benzothiazole and quinazoline derivatives form an important classes of fused heterocyclic compounds with a wide range of biological activities such as antimicrobial (Schwartz et al., 1992), anticancer (Wolfe et al., 1990), antiinflammatory (Tereshima et al., 1995). As a part of our studies in this area, the molecular and crystal structures of the title compound have been determined and the results are presented here.

The title compound comprises a benzothiazole ring fused with quinazoline ring. X–ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The benzothiazole ring system is essentially planar with a maximum deviation of -0.0127 (16)Å for the C7 atom. The quinazoline ring system is also essentially planar with the maximum deviation of -0.1588 (15)Å for the N1 atom. The dihedral angle between the benzothiazole and quinazoline ring systems are almost coplanar with a dihedral angle of 3.02 (5)° between them.

In the benzothiazole ring system, the oxygen atoms (O1 and O2) attached to the sulfur atom are significantly deviate from the least square plane of the ring system by 1.2231 (14)Å and -1.1989 (15)Å, respectively. The thiazole ring (C1/C6/C7/N1/S1) forms a dihedral angle of 0.34 (8)° and 3.15 (6)° with the phenyl ring (C1–C6) and the quinazoline ring system, respectively. The phenyl ring (C9–C14) forms the dihedral angles of 5.01 (8)° and 5.41 (7)° with the pyrimidine ring (N1/N2/C7–C10) and the phenyl ring (C1–C6), respectively. The title compound exibits the structural similarities with already reported structures (Khan et al., 2012; Grundt et al., 2010).

The crystal packing is stabilized by C2—H2···O1ⁱ intermolecular non–classical hydrogen bond (Table 1). The crystal packing is further stabilized by π···π interactions, with Cg1···Cg4ⁱⁱ and Cg3···Cg4ⁱⁱ distances being 3.7568 (8)Å and 3.8846 (9)Å, respectively, where Cg1 is the centre of gravity of (C1/C6/C7/N1/S1) ring; Cg3 is the centre of gravity of (C1–C6) ring; Cg4 is the centre of gravity of (C9–C14) ring. The symmetry codes: (i) -1/2+x, y, 1/2-z; (ii) -x, 1-y, 1-z. The packing view of the title compound is shown in Fig. 2.

Experimental

A solution of Saccharin (0.91 g, 5 mmol) and o–amino benzyl alcohol (0.61 g, 5 mmol) in DMF (10 ml) was irradiated with microwaves in a 800 W domestic microwave oven for 2 minutes. The reaction solution was cooled and poured over crushed ice (200 g). The precipitated product was filtered and desiccated over anhydrous CaCl₂. The resulting filetered product was subjected to crystallization by slow evaporation of the solvent resulting in single crystals suitable for XRD studies.