Different molecular assemblies in two new phosphoric triamides with the same C(O)NHP(O)(NH)2 skeleton: crystallographic study and Hirshfeld surface analysis

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Different molecular assemblies in two new phosphoric triamides with the

same C(O)NHP(O)(NH)

skeleton: crystallographic study and Hirshfeld

surface analysis

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Anahid Saneei

_{, Mehrdad Pourayoubi*}

_{, Titus A. Jenny}

_{, Aurelien Crochet}

_{, Katharina}

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M. Fromm

_{, Ekaterina S. Shchegravina}

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_{Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad,}

Iran, Tel: +985138805535, Fax: +985138807153, P.O. Box: 9177948974

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_{Department of Chemistry, University of Fribourg, Rte du Musée 9 Ch-1700 Fribourg,}

Switzerland

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_{Fribourg Centre for Nanomaterial’s, FriMat, University of Fribourg, Chemin du Musée 3,}

CH-1700 Fribourg, Switzerland

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_{Department of Organic Chemistry, UNN Lobachevsky State University, Gagarin av., 23,}

Nizhny Novgorod, Russia

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_{Corresponding author, e-mail: pourayoubi@um.ac.ir (Mehrdad Pourayoubi)}

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Received [Dates will be filled in by the Editorial office]

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List of Figures

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Fig. S1. IR spectrum of compound 1.

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Fig. S2. Mass spectrum of compound 1.

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Fig. S3. 31_{P NMR spectrum of compound 1 (d6-DMSO).}

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Fig. S4. 1_{H NMR spectrum of compound 1 (d6-DMSO).}

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Fig. S5. 13_{C NMR spectrum of compound 1 (d6-DMSO).}

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Fig. S6. 1_H–15_{N HSQC spectrum of compound 1.}

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Fig. S7. 1_H–13_{C HMQC spectrum of compound 1.} 35

Fig. S8. 1_H–13_{C HMBC spectrum of compound 1.} 36

Fig. S9. IR spectrum of compound 2.

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Fig. S10. Mass spectrum of compound 2.

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Fig. S11. 31_{P NMR spectrum of compound 2 (d6-DMSO).}

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Fig. S12. 1_{H NMR spectrum of compound 2 (d6-DMSO).}

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Fig. S13. 13_{C NMR spectrum of compound 2 (d6-DMSO).}

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Fig. S14. 1_H–15_{N HSQC spectrum of compound 2.}

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Fig. S15. 1_H–13_{C HMQC spectrum of compound 2.}

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Fig. S16. 1_H–13_{C HMBC spectrum of compound 2.}

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Fig. S1. IR spectrum of compound 1.

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Fig. S2. Mass spectrum of compound 1.

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Fig. S3. 31_{P NMR spectrum of compound 1 (d6-DMSO).}

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Fig. S4. 1_{H NMR spectrum of compound 1 (d6-DMSO).}

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Fig. S5. 13_{C NMR spectrum of compound 1 (d6-DMSO).}

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Fig. S6. 1_H–15_{N HSQC spectrum of compound 1.}

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Fig. S7. 1_H–13_{C HMQC spectrum of compound 1.} 72

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Fig. S8. 1_H–13_{C HMBC spectrum of compound 1.} 75

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Fig. S9. IR spectrum of compound 2.

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Fig. S10. Mass spectrum of compound 2.

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Fig. S11. 31_{P NMR spectrum of compound 2 (d6-DMSO).}

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Fig. S12. 1_{H NMR spectrum of compound 2 (d6-DMSO).}

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Fig. S13. 13_{C NMR spectrum of compound 2 (d6-DMSO).}

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Fig. S14. 1_H–15_{N HSQC spectrum of compound 2.}

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Fig. S15. 1_H–13_{C HMQC spectrum of compound 2.}

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Fig. S16. 1_H–13_{C HMBC spectrum of compound 2.}