1174
J Chem Crystallogr (2012) 42:1170–1175
7. Michelin RA, Pombeiro AJL, Guedes da Silva MFC (2001)
Coord Chem Rev 218:75
8. Vignolle J, Catton X, Bourissou D (2009) Chem Rev 109:3333
9. Glorius F (2007) Top Organomet Chem 21:1
Pt–C, and C–N bond lengths ranging from 2.305–2.324,
˚
1.90–1.92, and 1.13–1.16 A respectively.
Coordinated isocyanide is usually described as a meso-
meric hybrid of the bent carbene-type structure and the linear
isocyanide form. Clearly bent geometry due to the electronic
reason (if the steric effect is not taking place) was observed
for the early-late low-valent metal centers, e.g., Mo [40], W
[6, 7], and Re [41]. The CNR arrangement of the terminal
isocyanides at platinum centers is approximatelylinear at PtII
[14–16, 19, 42], PtI [43, 44], and Pt0 complexes [45, 46]. This
favors an insignificant contribution of the carbene-type form
of CNR ligands at these platinum centers. For both 4 and 5,
the low CNC bending and the triple bond character of the
C:N group favor the dominant contribution of the linear
isocyanide form and the minor contribution of the carbene-
type form in the mesomeric hybrid of the ligand; this state-
ment is in agreement with the previous results for other Pt
complexes [6, 7]. Our observations are also coherent with
the recently reported theoretical study conducted for
[PtCl2(CNMe)2], demonstrating the absence of an effective
p-back-donation and suggesting the single character of the
metal-ligand bonds [47].
10. Boyarskiy VP, Luzyanin KV, Kukushkin VY (2012) Coord Chem
Rev 256:2029
11. Cavell KJ, McGuiness DS (2007) Palladium complexes with
carbonyl, isocyanide and carbene ligands, Chap. 8.04. In: Canty
A (ed) Comprehensive organometallic chemistry III, 1st edn. vol
8. Elsevier, Oxford, pp 197–268
12. Rourke JP (2007) Platinum complexes with carbonyl, isocyanide and
carbene ligands, Chap. 8.07 In: Canty A (ed) Comprehensive orga-
nometallic chemistry III, 1stedn. vol 8. Elsevier, Oxford, pp 405–444
13. Nolan SP, Navarro O (2007) C–C bond formation by cross-
coupling, Chap. 11.01. In: Canty A (ed) Comprehensive Orga-
nometallic Chemistry III, 1st edn. Elsevier, Oxford, vol 11,
pp 1–38, and references therein
14. Luzyanin KV, Pombeiro AJL, Haukka M, Kukushkin VY (2008)
Organometallics 27:5379
15. Luzyanin KV, Guedes da Silva MFC, Kukushkin VY, Pombeiro
AJL (2009) Inorg Chim Acta 362:833
16. Luzyanin KV, Tskhovrebov AG, Carias MC, Guedes da Silva
MFC, Pombeiro AJL, Kukushkin VY (2009) Organometallics
28:6559
17. Luzyanin KV, Tskhovrebov AG, Guedes da Silva MFC, Haukka
M, Pombeiro AJL, Kukushkin VY (2009) Chem Eur J 15:5969
18. Tskhovrebov AG, Luzyanin KV, Dolgushin FM, Guedes da Silva
MFC, Pombeiro AJL, Kukushkin VY (2011) Organometallics
30:3362
19. Tskhovrebov AG, Luzyanin KV, Kuznetsov ML, Sorokoumov
VN, Balova IA, Haukka M, Kukushkin VY (2011) Organome-
tallics 30:863
Supporting Information
20. Chay RS, Luzyanin KV (2012) Inorg Chim Acta 380:322
21. Chay RS, Luzyanin KV, Kukushkin VY, Guedes da Silva MFC,
Pombeiro AJL (2012) Organometallics 31:2379
Full crystallographic data for compounds 4 and 5 have
been deposited with the Cambridge Crystallographic Data
Centre, deposition numbers CCDC 863905 and 863906.
Copy may be obtained free of charge from the Director
CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax:
?44 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk).
˚
22. Kukushkin VY, Oskarsson A, Elding LI (1997) Inorg Synth
31:279
23. Svensson P, Lovqvist K, Kukushkin VY, Oskarsson A (1995)
˚
¨
Acta Chem Scand 49:72
24. Bokach NA, Kuznetsova TV, Simanova SA, Haukka M, Pom-
beiro AJL, Kukushkin VY (2005) Inorg Chem 44:5152
25. Otwinowski Z, Minor W (1997) Processing of X-ray diffraction
data collected in Oscillation Mode. In Carter CW, Sweet J (eds)
Methods in enzymology, Macromolecular Crystallography Part
A, Academic Press, New York, pp 307–326
Acknowledgments The authors are obliged to Federal Grant-in-Aid
Program ‘‘Human Capital for Science and Education in Innovative
Russia’’ (Governmental Contract No. P1294 from 09/06/2010), Russian
Fund of Basic Research (grant 11-03-12044-ofim), Saint Petersburg
State University (research grant 2011–2013), and RAS Presidium
Subprogram coordinated by N.T. Kuznetsov. This work has been
26. Duisenberg AJM, Kroon-Batenburg LMJ, Schreurs AMM (2003)
J Appl Cryst 36:220
27. Palatinus L, Chapuis G (2007) J Appl Cryst 40:786
28. Burla MC, Camalli M, Carrozzini B, Cascarano GL, Giacovazzo
C, Polidori G, Spagna R (2005) J Appl Cryst 38:381
29. Farrugia LJ (1999) J Appl Cryst 32:837
ˆ
partially supported by the Fundac¸a˜o para a Ciencia e a Tecnologia
(FCT), Portugal (including FCT projects PTDC/QUI–QUI/098760/
2008, PTDC/QUI–QUI/109846/2009, and PEst-OE/QUI/UI0100/
2011). K.V.L. express gratitude to the FCT and Instituto Superior
30. Sheldrick GM (2008) SADABS—Bruker Nonius scaling and
absorption correction. Bruker AXS, Inc, Madison
31. Sheldrick GM (2008) Acta Cryst A64:112
´ ˆ
Tecnico (IST) for a research contract (Ciencia 2008 program).
32. Bonati F, Minghetti F (1970) J Organomet Chem 24:251
33. Michelin RA, Zanotto L, Braga D, Sabatino P, Angelici RJ
(1988) Inorg Chem 27:85
References
¨
1. Wang W, Domling A (2009) J Comb Chem 11:403
2. Wang W, Ollio S, Herdtweck E, Domling A (2010) J Org Chem
34. Michelin RA, Zanotto L, Braga D, Sabatino P, Angelici RJ
(1988) Inorg Chem 27:93
¨
76:637
3. Srivastava S, Beck B, Wang W, Czarna A, Holak TA, Domling A
35. Kukushkin VY (1988) Zh Neorg Khim 33:1905
36. Kukushkin VY (1988) Russ J Inorg Chem (Engl Transl) 33:1085
37. Davies JA, Hockensmith CM, Kukushkin VY, Kukushkin YN
(1996) Synthetic coordination chemistry: principles and practice.
World Scientific, Singapore
¨
(2009) J Comb Chem 11:631
¨
4. Domling A, Ugi I (2000) Angew Chem Int Ed 39:3168
5. Hahn FE (1993) Angew Chem Int Ed 32:650
6. Pombeiro AJL, Guedes da Silva MFC, Michelin RA (2001)
Coord Chem Rev 218:43
38. Bertani R, Mozzon M, Michelin RA, Benetollo F, Bombieri G,
Castilho TJ, Pombeiro AJL (1991) Inorg Chim Acta 189:175
123