Crystal structure of ethyl 4-(2-chloro­phen­yl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzo­thia­zole-3-carboxyl­ate

Balbir Kumar; Manmeet Kour; Satya Paul; Rajni Kant; Vivek K Gupta

doi:10.1107/S2056989015014905

. 2015 Aug 22;71(Pt 9):o669. doi: 10.1107/S2056989015014905

Crystal structure of ethyl 4-(2-chlorophenyl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate

Balbir Kumar ^a, Manmeet Kour ^b, Satya Paul ^b, Rajni Kant ^a, Vivek K Gupta ^a,^*

PMCID: PMC4555405 PMID: 26396895

Abstract

In the title compound, C₂₀H₁₇ClN₂O₂S, the dihedral angle between the planes of the benzothiazole fused ring system (r.m.s. deviation = 0.024 Å) and the chlorobenzene ring is 89.62 (12)°. The ester C—O—C—C side chain has an anti orientation [torsion angle = −155.2 (3)°]. In the crystal, weak aromatic π–π stacking interactions are observed between the phenyl and pyrimidine rings [centroid–centroid seperation = 3.666 (2) Å].

Keywords: crystal structure; pyrimido[2,1-b][1,3]benzothiazole; ester; biological activity

Related literature

For biological activities of benzothiazoles, see: Landreau et al. (2002 ▸); Russo et al. (1985 ▸). For a related structure, see: Sankar et al. (2015 ▸).

Experimental

Crystal data

C₂₀H₁₇ClN₂O₂S
M _r = 384.87
Triclinic,
a = 8.9049 (8) Å
b = 8.9275 (10) Å
c = 12.3564 (11) Å
α = 88.434 (8)°
β = 83.536 (7)°
γ = 66.201 (10)°
V = 892.90 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▸) T _min = 0.880, T _max = 1.000
6440 measured reflections
3477 independent reflections
2275 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.142
S = 1.03
3477 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015014905/hb7475sup1.cif

e-71-0o669-sup1.cif^{(25.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014905/hb7475Isup2.hkl

e-71-0o669-Isup2.hkl^{(167KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015014905/hb7475Isup3.cml

Click here for additional data file.^{(1.5MB, tif)}

ORTEP . DOI: 10.1107/S2056989015014905/hb7475fig1.tif

ORTEP view of the molecule with displacement ellipsoids drawn at the 40% probability level.

Click here for additional data file.^{(2.4MB, tif)}

a . DOI: 10.1107/S2056989015014905/hb7475fig2.tif

The packing arrangement of molecules viewed down the a axis.

CCDC reference: 1406433

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

RK acknowledges the Department of Science & Technology for single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.

supplementary crystallographic information

S1. Experimental

To a mixture of ethylacetoacetate (1.0 mmol, 0.13 g), 2-chlorobenzadehyde (1.0 mmol, 0.14 g) and 2-aminobenzothiazole (1.0 mmol, 0.152 g) in a round bottom flask (25 ml), C/TiO₂·SO₃·SbCl₂ (0.1 g) was added and the reaction mixture was heated at 363 K under solvent-free conditions for 1 h. Hot ethanol (2 × 5 ml) was added to the reaction mixture and the catalyst was separated by simple filteration. Removal of the solvent under reduced pressure afforded the product, which was further crystallized from ethanol as yellow crystals (Yield: 88%).