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1 ISSN Inorganic compounds Metal-organic compounds Organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Editors: W.T. A. Harrison, J. Simpson and M. Weil Bis(2,2 -bipyridine){ethyl 4 -[N-(4-carbamoylphenyl)carbamoyl]-2,2 -bipyridine-4-carboxylate}ruthenium(ii) bis[hexafluoridophosphate(v)] Masanari Hirahara, Shigeyuki Masaoka and Ken Sakai Acta Cryst. (2009). E65, m228 m229 This open-access article is distributed under the terms of the Creative Commons Attribution Licence which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. Volume 61 Part 11 November 2005 Acta Crystallographica Section E Structure Reports Online Editors: W. Clegg and D. G. Watson Acta Crystallographica Section E: Structure Reports Online is the IUCr s highly popular open-access structural journal. It provides a simple and easily accessible publication mechanism for the growing number of inorganic, metal-organic and organic crystal structure determinations. The electronic submission, validation, refereeing and publication facilities of the journal ensure very rapid and high-quality publication, whilst key indicators and validation reports provide measures of structural reliability. In 2007, the journal published over 5000 structures. The average publication time is less than one month. journals.iucr.org International Union of Crystallography * Chester Crystallography Journals Online is available from journals.iucr.org Acta Cryst. (2009). E65, m228 m229 Hirahara et al. [Ru(C 10 H 8 N 2 ) 2 (C 21 H 18 N 4 O 4 )](PF 6 ) 2

2 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Bis(2,2 0 -bipyridine){ethyl 4 0 -[N-(4- carbamoylphenyl)carbamoyl]-2,2 0 -bipyridine-4-carboxylate}ruthenium(ii) bis[hexafluoridophosphate(v)] Masanari Hirahara, Shigeyuki Masaoka and Ken Sakai* Department of Chemistry, Faculty of Science, Kyushu University, Hakozaki , Higashi-ku, Fukuoka , Japan Correspondence ksakai@chem.kyushu-univ.jp Received 19 November 2008; accepted 19 January 2009 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; R factor = 0.043; wr factor = 0.113; data-to-parameter ratio = V = (11) Å 3 Z =4 Mo K radiation Data collection Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.717, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections Table 1 Selected bond lengths (Å). Ru1 N (3) Ru1 N (3) Ru1 N (3) = 0.55 mm 1 T = 100 (s.u.?) K mm measured reflections 9357 independent reflections 6405 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.79 e Å 3 min = 0.48 e Å 3 Ru1 N (3) Ru1 N (3) Ru1 N (3) In the title compound, [Ru(C 10 H 8 N 2 ) 2 (C 21 H 18 N 4 O 4 )](PF 6 ) 2, the Ru II complex cation reveals a slightly distorted octahedral coordination. The coordination bonds of the 4,4 0 -substituted bipyridyl donors [Ru N = (3) and (3) Å] are shorter than those of the 2,2 0 -bipyridyl donors [Ru N1 = (3) (3) Å], due to the electron-withdrawing effects of the substituents at the 4,4 0 -positions. The angles between the pyridyl planes of the three bipyridyl ligands are 1.5 (2), 6.3 (3) and 8.7 (2), respectively. The cations are connected by anions via N HF interactions. Related literature For related literature, see: Gillaizeau-Gauthier et al. (2001); Ozawa & Sakai (2007); Ozawa et al. (2006, 2007); Sakai & Ozawa (2007); Sakai et al. (1993). For discussion of attractive interactions between negatively-charged atoms and alpha C atoms from heterocyclic rings, see: Schottel et al. (2008). Table 2 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA N7 H7F2 i (4) 168 N8 H8BF10 i (5) 139 Symmetry code: (i) x; y þ 1 2 ; z þ 1 2. Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: KENX (Sakai, 2004); software used to prepare material for publication: SHELXL97, TEXSAN (Molecular Structure Corporation, 2001), KENX and ORTEPII (Johnson, 1976). This work was in part supported by a Grant-in-Aid for Scientific Research (A) (No ), a Grant-in-Aid for Specially Promoted Research (No ), and a Grant-in- Aid for the Global COE Program ( Science for Future Molecular Systems ) from the Ministry of Education, Culture, Sports, Science and Technology of Japan. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2198). Experimental Crystal data [Ru(C 10 H 8 N 2 ) 2 (C 21 H 18 N 4 O 4 )]- (PF 6 ) 2 M r = Monoclinic, P2 1 =c a = (3) Å b = (2) Å c = (3) Å = (2) References Bruker (2004). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Gillaizeau-Gauthier, I., Odobel, F., Alebbi, M., Argazzi, R., Costa, E., Bignozzi, C. A., Qu, P. & Meyer, G. J. (2001). Inorg. Chem. 40, Johnson, C. K. (1976). ORTEPII. Report ORNL Oak Ridge National Laboratory, Tennessee, USA. Molecular Structure Corporation (2001). TEXSAN. MSC, The Woodlands, Texas, USA. Ozawa, H., Haga, M. & Sakai, K. (2006). J. Am. Chem. Soc. 128, Ozawa, H. & Sakai, K. (2007). Chem. Lett. 36, Ozawa, H., Yokoyama, Y., Haga, M. & Sakai, K. (2007). Dalton Trans. pp m228 Hirahara et al. doi: /s Acta Cryst. (2009). E65, m228 m229

3 metal-organic compounds Sakai, K. (2004). KENX. Kyushu University, Japan. Sakai, K., Kizaki, Y., Tsubomura, T. & Matumoto, K. (1993). J. Mol. Catal. 79, Sakai, K. & Ozawa, H. (2007). Coord. Chem. Rev. 251, Schottel, B. L., Chifotides, H. T. & Dunbar, K. R. (2008). Chem. Soc. Rev. 37, Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, Acta Cryst. (2009). E65, m228 m229 Hirahara et al. [Ru(C 10 H 8 N 2 ) 2 (C 21 H 18 N 4 O 4 )](PF 6 ) 2 m229

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