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Synthesis, Characterization and Crystal Structure of Thiadiazoles Derived from Aroylthiourea

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Abstract

Three thiadiazole derivatives, (Z)-N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidine)benzamide (I), (Z)-N-(2H-thiazolo[3,2-b] [1,2,4] thiadiazolo-2-ylidine)thiophene-2-carboxamide(II) and (Z)-N-(2H-[1,2,4] thiadiazolo[2,3-a]pyridine-2-ylidine)thiophene-2-carboxamide(III), have been synthesized and examined by X-ray crystallography and NMR spectroscopy. I, C13H9N3OS, is monoclinic with space group P21/n and cell constants a = 6.2699(11) Å, b = 18.025(4) Å, c = 10.207(2) Å, β = 95.088(19)°, V = 1149.0(4) Å3 and Z = 4. II, C9H5N3OS3, is orthorhombic with space group Pbca and cell constants a = 12.52148(17) Å, b = 11.27270(18) Å, c = 14.9154(3) Å, V = 1370.3(7) Å3 and Z = 8. III, C11H7N3OS2, is monoclinic with space group P21/c, and cell constants a = 10.9171(15) Å, b = 18.227(2) Å, c = 11.8019(16) Å, β = 108.955(14)°, V = 1370.3(7) Å3, Z = 8. In III, two independent molecules crystallize in the asymmetric unit (Z = 2). The pyridothiadiazole fused ring in I and III, and thiazolothiadiazole fused ring in II, are planar with a maximum deviation of 0.012(3) (I), 0.011(2) and 0.006(3) (III) and 0.029(1) (II) Å, respectively. The dihedral angle between mean planes of the pyridothiadiazole ring and benzamide and thiocarboxamide rings are 3.48(13)°(I), 0.97(25)° and 3.68(31)° (III) while in between thiazolothiadiazole ring and thiocarboxamide ring in II is, 5.27(12)°. The thiophene rings in II and III are disordered over two sets of site in a 0.5028(19): 0.4972(19) (II) and 0.624(4):0.376(4) (molecule A) and 0.710:0.290(4) (molecule B) ratio (III). Weak C–H···O, C–H···N (I and II) and C–H···O (III) intermolecular hydrogen bond interactions help to stabilize crystal packing in each of their unit cells. It is also supported by weak intermolecular Cg···Cg π···π and C–H···Cg π-ring interactions which gives additional support to molecular packing stability leading to supramolecular layers.

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Synthesis, spectroscopic studies and crystal structures of three thiadiazole derivatives.

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Acknowledgments

The authors are grateful to Banaras Hindu University, Varanasi, India for the financial assistance and research scholarship to DPS. RJB acknowledges the NSF—MRI program (Grant No. CHE0619278) for funds to purchase the X-ray diffractometer. SKG wishes to acknowledge the USIEF for the award of a Fulbright–Nehru Senior Research Fellowship.

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Authors and Affiliations

  1. Department of Chemistry (MMV), Banaras Hindu University, Varanasi, 221 005, India

    Durga P. Singh & Seema Pratap

  2. Department of Chemistry, Howard University, 525 College Street NW, Washington, DC, 20059, USA

    Ray J. Butcher

  3. School of Studies in Chemistry, Jiwaji University, Gwalior, 474 011, India

    Sushil K. Gupta

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  1. Durga P. Singh
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  2. Seema Pratap
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Correspondence to Seema Pratap.

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Singh, D.P., Pratap, S., Butcher, R.J. et al. Synthesis, Characterization and Crystal Structure of Thiadiazoles Derived from Aroylthiourea. J Chem Crystallogr 44, 115–122 (2014). https://doi.org/10.1007/s10870-013-0488-9

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