1690
M. Toghraee et al. / Polyhedron 30 (2011) 1680–1690
[28] K. Gholivand, Z. Shariatinia, S.M. Mashhadi, F. Daeepour, N. Farshidnasab, H.R.
(b) Two H-acceptors–three H-donors: only an anti situation has
Mahzouni, N. Taheri, S. Amiri, S. Ansar, Polyhedron 28 (2009) 307.
[29] K. Gholivand, H. Mostaanzadeh, Z. Shariatinia, N. Oroujzadeh, Main Group
Chem. 5 (2006) 95.
been found in acyclic molecules, RC(O)NHP(O)[NHR0]2, and one
reported diazaphosphole with different kinds of linear H-bonded
[30] H. Mostaanzadeh, Anal. Sci. 24 (2008) x255.
arrangements;
a gauche orientation exists in three reported
[31] K. Gholivand, M. Pourayoubi, H. Mostaanzadeh, Anal. Sci. 20 (2004) x51.
[32] K. Gholivand, C.O. Della Védova, A. Anaraki Firooz, A. Madani Alizadehgan, M.C.
Michelini, R. Pis Diez, J. Mol. Struct. 750 (2005) 64.
diazaphosphorinanes, RC(O)NHP(O)X (X = NHYNH, Y = C10H6,
CH2C(CH3)2CH2) with 1-D and 2-D HB arrangements.
[33] K.E. Gubina, V.A. Ovchynnikov, V.M. Amirkhanov, V.V. Skopenko, O.V. Shishkin,
Z. Naturforsch. B 55 (2000) 495.
[34] K. Gholivand, Z. Hosseini, M. Pourayoubi, Z. Shariatinia, Z. Anorg. Allg. Chem.
631 (2005) 3074.
[35] K. Gholivand, Z. Shariatinia, Struct. Chem. 18 (2007) 95.
[36] K. Gholivand, F. Mojahed, M. Salehi, A. Madani Alizadehgan, Anal. Sci. 22
(2006) x13.
[37] O.N. Rebrova, V.N. Byushkin, T.I. Malinovskii, L.D. Protsenko, T.N. Dneprova,
Proc. Nat. Acad. Sci. USSR 266 (1982) 1391.
As a non-anti orientation may be required for the application of
CPAs as chelating ligands, we wish to understand the factors affect-
ing the preference of a non-anti orientation in the C(O)NHP(O)
skeleton and are continuing work in this area.
Acknowledgements
[38] K. Gholivand, Z. Shariatinia, M. Pourayoubi, S. Farshadian, Z. Naturforsch. B 60
(2005) 1021.
[39] K. Gholivand, Z. Shariatinia, M. Pourayoubi, Z. Anorg. Allg. Chem. 632 (2006)
160.
Support of this investigation by Ferdowsi University of Mashhad
is gratefully acknowledged. The authors thank Dr. G. Bogdanovic for
the CSD search.
[40] A. Tarahhomi, M. Pourayoubi, A.L. Rheingold, J.A. Golen, Struct. Chem. 22
(2011) 201.
Appendix A. Supplementary data
[41] K. Gholivand, Z. Shariatinia, M. Pourayoubi, Polyhedron 25 (2006) 711.
[42] A. Mahmoudi, R. Hadjikhani, Z. Kristallogr, NCS 222 (2007) 313.
[43] A. Mahmoudi, A.H. Amin, Acta Crystallogr., Sect. E 63 (2007) o2031.
[44] K.E. Gubina, V.M. Amirkhanov, Z. Naturforsch. B 55 (2000) 1015.
[45] O.N. Rebrova, V.N. Biyushkin, T.I. Malinovskii, L.D. Protsenko, T.N. Dneprova,
Proc. Nat. Acad. Sci. USSR 300 (1988) 361.
[46] F. Sabbaghi, M. Pourayoubi, M. Toghraee, V. Divjakovic, Acta Crystallogr., Sect.
E 66 (2010) o344.
[47] K. Gholivand, H. Mostaanzadeh, T. Koval, M. Dusek, M.F. Erben, H. Stoeckli
Evans, C.O. Della Védova, Acta Crystallogr., Sect. B 66 (2010) 441.
[48] F. Sabbaghi, M. Rostami Chaijan, M. Pourayoubi, Acta Crystallogr., Sect. E 66
(2010) o1754.
[49] M. Pourayoubi, F. Sabbaghi, J. Chem. Crystallogr. 39 (2009) 874.
[50] K. Gholivand, H. Mostaanzadeh, T. Koval, M. Dusek, M.F. Erben, C.O. Della
Védova, Acta Crystallogr., Sect. B 65 (2009) 502.
[51] K. Gholivand, F. Mojahed, A. Madani Alizadehgan, H.R. Bijanzadeh, Z. Anorg.
Allg. Chem. 632 (2006) 1570.
[52] O.N. Rebrova, V.N. Biyushkin, T.I. Malinovsky, V.M. Ovrutsky, L.D. Protsenko,
T.N. Dneprova, M.D. Mazus, Proc. Nat. Acad. Sci. USSR 324 (1992) 103.
[53] S. Dehghanpour, R. Welter, A. Hamady Barry, F. Tabasi, Acta Crystallogr., Sect. E
64 (2008) o633.
[54] C.E. Strasser, X. Sheng, D.A. Safin, H.G. Raubenheimer, R.C. Luckay, Acta
Crystallogr., Sect. E 65 (2009) o2926.
CCDC 791342, 791344, 791343 and 791345 contains the sup-
plementary crystallographic data for (1), (2), (3) and (4). These data
tre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-
033; or e-mail: deposit@ccdc.cam.ac.uk.
References
[1] T. Steiner, Angew. Chem., Int. Ed. 41 (2002) 48.
[2] (a) G. Gilli, F. Bellucci, V. Ferretti, V. Bertolasi, J. Am. Chem. Soc. 111 (1989) 1023;
(b) P. Gilli, V. Bertolasi, V. Ferretti, G. Gilli, J. Am. Chem. Soc. 116 (1994) 909.
[3] (a) G. Gilli, P. Gilli, J. Mol. Struct. 552 (2000) 1;
(b) P. Gilli, V. Bertolasi, L. Pretto, V. Ferretti, G. Gilli, J. Am. Chem. Soc. 126
(2004) 3845.
[4] M.C. Etter, J.C. MacDonald, Acta Crystallogr., Sect. B 46 (1990) 256.
[5] L.N. Kuleshova, P.M. Zorky, Acta Crystallogr., Sect. B 36 (1980) 2113.
[6] P.M. Zorky, L.N. Kuleshova, Zh. Strukt. Khim. 22 (1980) 153.
[7] M.C. Etter, Acc. Chem. Res. 23 (1990) 120.
[55] O.N. Rebrova, V.N. Biyushkin, T.I. Malinovskii, L.D. Protsenko, T.N. Dneprova,
Proc. Nat. Acad. Sci. USSR 302 (1988) 1108.
[8] J.C. MacDonald, G.M. Whitesides, Chem. Rev. 94 (1994) 2383.
[9] (a) N.G. Zabirov, O.K. Pozdeev, F.M. Shamsevaleev, R.A. Cherkasov, G.H.
Gilmanova, Pharm. Chem. J. 23 (1989) 423;
[56] O.N. Rebrova, V.N. Byushkin, V.E. Zavodnik, T.I. Malinovskii, L.D. Protsenko,
T.N. Dneprova, Proc. Nat. Acad. Sci. USSR 280 (1985) 1133.
[57] K. Gholivand, N. Oroujzadeh, Z. Shariatinia, Heteroatom Chem. 21 (2010) 168.
[58] K. Gholivand, N. Oroujzadeh, Main Group Chem. 7 (2008) 251.
[59] L.I. Zhdanova, V.N. Byushkin, T.I. Malinovskii, L.D. Protsenko, Proc. Nat. Acad.
Sci. USSR 287 (1986) 119.
[60] L.I. Zhdanova, V.N. Byushkin, L.D. Protsenko, T.I. Malinovskii, Proc. Nat. Acad.
Sci. USSR 288 (1986) 1354.
[61] E.B. Rusanov, A.N. Chernega, M.I. Povolotsky, L.N. Markovsky, Ukr. Khim. Zh.
(Russ) 65 (1999) 69.
(b) V. Amirkhanov, C. Janczak, L. Macalik, J. Hanuza, J. Legendziewicz, J. Appl.
Spectrosc. 62 (1995) 5;
(c) V. Amirkhanov, V. Ovchinnikov, J. Legendziewicz, A. Graczyk, J. Hanuza, L.
Macalik, Acta Phys. Polon. 90 (1996) 455.
[10] K. Gholivand, Z. Shariatinia, S. Ansar, S.M. Mashhadi, F. Daeepour, Struct.
Chem. 20 (2009) 481.
[11] K. Gholivand, M. Pourayoubi, Z. Anorg. Allg. Chem. 630 (2004) 1330.
[12] K. Gholivand, A. Madani Alizadehgan, F. Mojahed, A. Anaraki Firooz, S. Afr. J.
Chem. 60 (2007) 91.
[13] K.E. Gubina, O.A. Maslov, E.A. Trush, V.A. Trush, V.A. Ovchynnikov, S.V.
Shishkina, V.M. Amirkhanov, Polyhedron 28 (2009) 2661.
[14] V.M. Amirkhanov, V.A. Ovchynnikov, T. Glowiak, H. Kozlowski, Z. Naturforsch.
B 52 (1997) 1331.
[15] K.O. Znovjyak, V.A. Ovchynnikov, T.Yu. Sliva, S.V. Shishkina, V.M. Amirkhanov,
Acta Crystallogr., Sect. E 65 (2009) o2812.
[16] K. Gholivand, M. Pourayoubi, Z. Shariatinia, H. Mostaanzadeh, Polyhedron 24
(2005) 655.
[17] K. Gholivand, A. Madani Alizadehgan, S. Arshadi, A. Anaraki Firooz, J. Mol.
Struct. 791 (2006) 193.
[18] K. Gholivand, A. Madani Alizadehgan, F. Mojahed, P. Soleimani, Polyhedron 27
(2008) 1639.
[19] V.A. Ovchynnikov, V.M. Amirkhanov, T.P. Timoshenko, T. Glowiak, H.
Kozlowski, Z. Naturforsch. B 53 (1998) 481.
[62] O.N. Rebrova, V.N. Byushkin, T.I. Malinovskii, L.D. Protsenko, T.N. Dneprova,
Proc. Nat. Acad. Sci. USSR 286 (1986) 891.
[63] K.E. Gubina, V.A. Ovchynnikov, V.M. Amirkhanov, T.Y. Sliva, V.V. Skopenko, T.
Glowiak, H. Kozlowski, Z. Naturforsch. B 54 (1999) 1357.
[64] K. Gholivand, F. Afshar, Z. Shariatinia, K. Zare, Struct. Chem. 21 (2010) 629.
[65] Data Collection and Processing Software, Vers. 1, Oxford Diffraction Ltd., 68
Milton Park, OX14 4RX, UK, 2006.
[66] A.J.C. Wilson (Ed.), International Tables for X-ray Crystallography, vol. C,
Kluwer Academic Publishers, Dordrecht, 1992, pp. 500–502, 219–222, 193–
199.
[67] A. Altornare, G. Gascarano, C. Giacovazzo, A. Guagliardi, SIR92, J. Appl. Cryst. 26
(1993) 343.
[68] C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L.
Rodriguez-Monge, R. Taylor, J. Van de Streek, P.A. Wood, J. Appl. Cryst. 41
(2008) 466.
[69] G.M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, Institüt
für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400
Gottingen, Germany, 1997.
[70] H.D. Flack, Acta Crystallogr., Sect. A 39 (1983) 876.
[71] R.S. Drago, Physical Methods for Chemists, second ed., Saunders College
Publishing, Florida, 1992, p. 254.
[20] V.M. Amirkhanov, V.A. Ovchynnikov, V.A. Trush, V.V. Scopeko, Zh. Org. Khim.
(Russ) 32 (1996) 356.
[21] O.V. Amirkhanov, O.V. Moroz, K.O. Znovjyak, E.A. Trush, T.Y. Sliva, Acta
Crystallogr., Sect. E 66 (2010) o1102.
[22] K. Gholivand, Z. Shariatinia, M. Pourayoubi, Z. Anorg. Allg. Chem. 631 (2005)
961.
[23] K. Gholivand, F. Mojahed, A.M. Alizadehgan, Pol. J. Chem. 81 (2007) 393.
[24] K. Gholivand, F. Mojahed, A.M. Alizadehgan, Pol. J. Chem. 81 (2007) 1829.
[25] M. Yazdanbakhsh, F. Sabbaghi, R. Boese, Z. Kristallogr, NCS 222 (2007) 331.
[26] P.M. Narula, C.S. Day, B.A. Powers, M.A. Odian, A. Lachgar, W.T. Pennington, R.E.
Noftle, Polyhedron 18 (1999) 1751.
[72] F. Sabbaghi, M. Pourayoubi, M. Rostami Chaijan, unpublished results.
[73] G. Wipff, C. Boehme, Inorg. Chem. 41 (2002) 727.
[74] K. Gholivand, H.R. Mahzouni, M. Pourayoubi, S. Amiri, Inorg. Chim. Acta 363
(2010) 2318.
[75] K. Gholivand, N. Oroujzadeh, F. Afshar, J. Organomet. Chem. 695 (2010) 1383.
[76] A. Bondi, J. Phys. Chem. 68 (1964) 441.
[27] S. Dehghanpour, R. Welter, A. Hamady Barry, F. Tabasi, Spectrochim. Acta A 75
(2010) 1236.