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Licensed Unlicensed Requires Authentication Published by De Gruyter (O) March 10, 2015

Bipodal benzoylthiocarbamic acid esters: crystal and molecular structures of R = Et (a polymorph), and of a binuclear Cu(I) complex, R = iPr

  • Nabihah Al Muna Mohd Nor , Jimmy Ahmad , Zanariah Abdullah , Siti Nadiah Abdul Halim , Alberto Otero-de-la-Roza EMAIL logo and Edward R.T. Tiekink EMAIL logo

Abstract

The crystal and molecular structure of a second polymorph (P21/n) of [1,4-ROC(=S)N(H)C(=O)C6H4C(=O)N(H)C(=S)OR], R = Et, is shown to have inversion symmetry and to have a more twisted conformation than the previously reported P43212 form which has 2-fold symmetry. Despite utilising equivalent atoms in forming intermolecular interactions, very distinct crystal packing patterns are observed. Crystal characteristics and theory (DFT) are consistent with the P43212 form being more stable, a conclusion correlated with the observation that this form is the overwhelming majority of the sample (PXRD). An analysis of a binuclear copper(I) complex containing the R = iPr analogue, reveals the neutral ligand to bind via the thione-S atom resulting in a distorted ClP2S tetrahedral geometry.


Corresponding authors: Alberto Otero-de-la-Roza, National Research Council of Canada, National Institute for Nanotechnology, 11421 Saskatchewa Drive, Edmonton, Alberta, Canada T6G 2M9, E-mail: ; and Edward R.T. Tiekink, Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, E-mail:

Acknowledgments

The support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR-MOHE/SC/12) is gratefully acknowledged. AOR thanks the Spanish Malta/Consolider initiative (no. CSD2007-00045) and Alberta Innovates Technology Futures (AITF) for funding.

References

[1] S. Y. Ho, R. P. A. Bettens, D. Dakternieks, A. Duthie, E. R. T. Tiekink. CrystEngComm2005, 7, 682.10.1039/b514254gSearch in Google Scholar

[2] F. S. Kuan, F. Mohr, P. P. Tadbuppa, E. R. T. Tiekink. CrystEngComm, 2007, 9, 574.10.1039/B701489ASearch in Google Scholar

[3] S. Y. Ho, E. C.-C. Cheng, E. R. T. Tiekink, V. W.-W. Yam. Inorg. Chem .2006, 45, 8165.Search in Google Scholar

[4] S. Y. Ho, E. R. T. Tiekink. CrystEngComm2007, 9, 368.Search in Google Scholar

[5] F. S. Kuan, S. Y. Ho, P. P. Tadbuppa, E. R. T. Tiekink. CrystEngComm2008, 10, 548.10.1039/b717198fSearch in Google Scholar

[6] J. Zukerman-Schpector, E. R. T. Tiekink. Z. Kristallogr.2008, 223, 233.Search in Google Scholar

[7] C. A. Ellis, M. A. Miller, J. Spencer, J. Zukerman-Schpector, E. R. T. Tiekink. CrystEngComm2009, 11, 1352.10.1039/b822555aSearch in Google Scholar

[8] C. I. Yeo, K. K. Ooi, A. Md. Akim, K. P. Ang, Z. A. Fairuz, S. N. B. A. Halim, S. W. Ng, H.-L. Seng, E. R. T. Tiekink. J. Inorg. Biochem.2013, 127, 24.Search in Google Scholar

[9] C. I. Yeo, J.-H. Sim, C.-H. Khoo, Z.-J. Goh, K. P. Ang, Y.-K. Cheah, Z. A. Fairuz, S. N. B. A. Halim, S. W. Ng, H.-L. Seng, E. R. T. Tiekink. Gold Bull.2013, 46, 145.Search in Google Scholar

[10] F. H. Allen. Acta Crystallogr.Sect. B2002, 58, 380.10.1107/S0108768102003890Search in Google Scholar PubMed

[11] H. Arslan, U. Florke, N. Kulcu. Spectrochim. Acta, Part A2007, 67, 936.10.1016/j.saa.2006.09.011Search in Google Scholar PubMed

[12] H. Insuasty, E. Castro, E. Sánchez, J. Cobo, C. Glidewell. Acta Crystallogr., Sect. C2010, 66, o141.10.1107/S0108270110005032Search in Google Scholar PubMed PubMed Central

[13] A. M. Plutin, M. Suárez, T. Machado, A. Álvarez, A. Rodríguez, R. Martínez, J. Duque, R. Martinez-Alvarez, N. Martin. ARKIVOC2010, 11, 276.10.3998/ark.5550190.0011.a23Search in Google Scholar

[14] G. Blewett, C. Esterhuysen, M. W. Bredenkamp, K. R. Koch. Acta Crystallogr., Sect. C2004, 60, o862.10.1107/S0108270104026587Search in Google Scholar PubMed

[15] G. Blewett, M. W. Bredenkamp, K. R. Koch. Acta Crystallogr., Sect. C2005, 61, o469.10.1107/S0108270105018494Search in Google Scholar PubMed

[16] U. Schroder, L. Beyer, F. Dietze, R. Richter, S. Schmidt, E. Hoyer. J. Prakt. Chem. – Chem.-Zeitung1995, 337, 184.10.1002/prac.19953370141Search in Google Scholar

[17] X’Pert HighScore Plus. 2009. PANalytical B.V. Almelo, The Netherlands.Search in Google Scholar

[18] Agilent Technologies. CrysAlis PRO. Agilent Technologies, Santa Clara, CA, USA, 2014.Search in Google Scholar

[19] G. M. Sheldrick. Acta Crystallogr.2008, A64, 112.Search in Google Scholar

[20] L. J. Farrugia. J. Appl. Crystallogr.2012, 45, 849.Search in Google Scholar

[21] A. L. Spek. J. Appl. Crystallogr.2003, 36, 7.Search in Google Scholar

[22] K. Brandenburg, DIAMOND. Crystal Impact GbR, Bonn, Germany, 2006.Search in Google Scholar

[23] J. D. Gans, D. Shalloway. J. Mol. Graph. Model.2001, 19, 557.Search in Google Scholar

[24] P. Giannozzi, S. Baroni, N. Bonini, M. Calandra, R. Car, C. Cavazzoni, D. Ceresoli, G. L. Chiarotti, M. Cococcioni, I. Dabo, A. Dal Corso, S. de Gironcoli, S. Fabris, G. Fratesi, R. Gebauer, U. Gerstmann, C. Gougoussis, A. Kokalj, M. Lazzeri, L. Martin-Samos, N. Marzari, F. Mauri, R. Mazzarello, S. Paolini, A. Pasquarello, L. Paulatto, C. Sbraccia, S. Scandolo, G. Sclauzero, A. P. Seitsonen, A. Smogunov, P. Umari, R. M. Wentzcovitch. J. Phys. Condens. Matter, 2009, 21, 395502.10.1088/0953-8984/21/39/395502Search in Google Scholar PubMed

[25] J. P. Perdew, Y. Wang. Phys. Rev. B1986, 33, 8800.10.1103/PhysRevB.33.8800Search in Google Scholar

[26] J. P. Perdew, K. Burke, M. Ernzerhof. Phys. Rev. Lett.1996, 77, 3865.Search in Google Scholar

[27] A. D. Becke, E. R. Johnson. J. Chem. Phys.2007, 127, 154108.Search in Google Scholar

[28] A. Otero-de-la-Roza, E. R. Johnson. J. Chem. Phys.2012, 136, 174109.Search in Google Scholar

[29] A. Otero-de-la-Roza, E. R. Johnson. J. Chem. Phys.2012, 137, 054103.Search in Google Scholar

[30] A. Otero-de-la-Roza, B. H. Cao, I. K. Price, J. E. Hein, E. R. Johnson. Angew. Chem. Int. Ed.2014, 53, 7879.Search in Google Scholar

[31] P. E. Blochl. Phys. Rev. B1994, 50, 17953.10.1103/PhysRevB.50.17953Search in Google Scholar

[32] C. I. Yeo, S. N. A. Halim, S. W. Ng, S. L. Tan, J. Zukerman-Schpector, M. A. B. Ferreira, E. R. T. Tiekink. Chem.Commun.2014, 50, 5984.Search in Google Scholar


Supplemental Material

The online version of this article (DOI: 10.1515/zkri-2014-1820) offers supplementary material, available to authorized users.


Received: 2014-11-19
Accepted: 2015-1-21
Published Online: 2015-3-10
Published in Print: 2015-6-1

©2015 by De Gruyter

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