metal-organic compounds
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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN = (4) = (4) = (3) V = (7) Å 3 Z =1 Mo K radiation = mm 1 T = 295 K mm Bis[dichlorido(5,5 0 -dimethyl-2,2 0 -bipyridine-j 2 N,N 0 )gold(iii)] tetrachloridoaurate(iii) dichloridooaurate(i) Selvi Karaca, a Mehmet Akkurt, a * Nasser Safari, b Vahid Amani, b Orhan Büyükgüngör c and Anita Abedi d a Department of Physics, Faculty of Arts and Sciences, Erciyes University, Kayseri, Turkey, b Chemistry Department, Shahid Beheshti University, GC, Tehran, Iran, c Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun, Turkey, and d Department of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran Correspondence akkurt@erciyes.edu.tr Received 21 January 2009; accepted 21 February 2009 Key indicators: single-crystal X-ray study; T = 295 K; mean (C C) = Å; R factor = 0.042; wr factor = 0.112; data-to-parameter ratio = Data collection Stoe IPDS-2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T min = 0.054, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections Table 1 Selected bond lengths (Å). Au1 N (9) Au1 N (7) Au1 Cl (3) Au1 Cl (3) 9898 measured reflections 3651 independent reflections 3193 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 1.64 e Å 3 min = 1.91 e Å 3 Au2 Cl (5) Au2 Cl (3) Au3 Cl (3) The title compound, [Au III Cl 2 (C 12 H 12 N 2 )] 2 [Au III Cl 4 ][Au I Cl 2 ], contains three distinct types of Au atom. In the cation, the Au III atom is four-coordinated in a distorted square-planar arrangement by an N,N 0 -bidentate 5,5 0 -dimethyl-2,2 0 -bipyridine ligand and two terminal Cl atoms. In the [AuCl 4 ] anion, the centrosymmetric Au III atom has a square-planar coordination. The centrosymmetric [AuCl 2 ] anion is linear. Intra- and intermolecular C HCl hydrogen bonds help to establish the conformation and packing. Related literature For related stuctures, see: Abbate et al. (2000); Adams & Strähle (1982); Ahmadi, Amani & Khavasi (2008); Ahmadi, Dehghan, Amani & Khavasi (2008); Bjernemose et al. (2004); Hayoun et al. (2006); Hollis & Lippard (1983); McInnes et al. (1995); Yıldırım et al. (2008). Table 2 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA C1 H1Cl (11) 124 C8 H8Cl2 i (12) 169 C11 H11Cl (11) 122 Symmetry code: (i) x 1; y; z. Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X- AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999). The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-2 diffractometer (purchased under grant F.279 of the University Research Fund). NS, VA and AA are grateful to Shahid Beheshti University for financial support. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2902). Experimental Crystal data [AuCl 2 (C 12 H 12 N 2 )] 2 [AuCl 4 ][AuCl 2 ] M r = Triclinic, P1 a = (4) Å b = (4) Å c = (5) Å References Abbate, F., Orioli, P., Bruni, B., Marcon, G. & Messori, L. (2000). Inorg. Chim. Acta, 311, 1 5. Adams, H. N. & Strähle, J. (1982). Z. Anorg. Allg. Chem. 485, Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1156 m1157. Ahmadi, R., Dehghan, L., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1237. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, doi: /s Karaca et al. m335
2 metal-organic compounds Bjernemose, J. K., Raithby, P. R. & Toftlund, H. (2004). Acta Cryst. E60, m1719 m1721. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, Hayoun, R., Zhong, D. K., Rheingold, A. L. & Doerrer, L. H. (2006). Inorg. Chem. 45, Hollis, L. S. & Lippard, S. J. (1983). J. Am. Chem. Soc. 105, McInnes, E. J. L., Welch, A. J. & Yellowlees, L. J. (1995). Acta Cryst. C51, Sheldrick, G. M. (2008). Acta Cryst. A64, Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Yıldırım, S. Ö., Akkurt, M., Safari, N., Amani, V., McKee, V., Abedi, A. & Khavasi, H. R. (2008). Acta Cryst. E64, m1189 m1190. m336 Karaca et al. [AuCl 2 (C 12 H 12 N 2 )] 2 [AuCl 4 ][AuCl 2 ]
3 supporting information [doi: /s ] Bis[dichlorido(5,5 -dimethyl-2,2 -bipyridine-κ 2 N,N )gold(iii)] tetrachloridoaurate(iii) dichloridooaurate(i) Selvi Karaca, Mehmet Akkurt, Nasser Safari, Vahid Amani, Orhan Büyükgüngör and Anita Abedi S1. Comment Recently, we reported the synthesis and crystal structure of the [Au(dtbpy)Cl 2 ][AuCl 4 ].CH 3 CN, (II), (Yıldırım et al., 2008) [where dtbpy is 4,4 -di-tert-butyl-2,2 -bipyridine]. There are several Au III complexes, with formula, [AuCl 2 (N N)]X, such as [AuCl 2 (bipy)][bf 4 ], (III), (McInnes et al., 1995), [AuCl 2 (bipy)](no 3 ), (IV), (Bjernemose et al., 2004), [AuCl 2 (bipy)][aubr 4 ], (V), (Hayoun et al., 2006), [AuCl 2 (dmphen)][aucl 4 ], (VI), (Ahmadi, Amani et al., 2008) and [AuCl 2 (phen)]cl.h 2 O, (VII), (Abbate et al., 2000) [where bipy is 2,2 -bipyridine, dmphen is 4,7-diphenyl-1,10- phenanthroline and phen is 1,10-phenanthroline] have been synthesized and characterized by single-crystal X-ray diffraction methods. Two Au III complexes with formula, [AuCl 2 L 2 ]X, [AuCl 2 (py) 2 ][AuCl 4 ], (VIII), and [AuCl 2 (py) 2 ]Cl.H 2 O, (IX), (Adams & Strähle 1982) [py is pyridine] and two mixed-valence Au I Au III complexes, [Au(terpy)Cl] 2 [AuCl 2 ] 3 [AuCl 4 ], (X), (Hollis & Lippard, 1983) and [Au(dmpy) 2 ][AuCl 4 ], (XI), (Ahmadi, Dehghan et al., 2008) [where terpy is 2,2,2 -terpyridine and dmpy is 2,6-dimethylpyridine] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound (I). In the asymmetric unit of the title compound (I), (Fig. 1), there are one cation and two half-anions. In the cation, the Au III atom is four-coordinated in a distorted square-planar configuration by two N atoms from the ligand and two terminal Cl atoms. In the anion AuCl 4, the Au III atom has a square-planar coordination. The anion AuCl 2 is linear. In the cation, the Au Cl and Au N bond lengths and angles (Table 1) are in good agreement with the corresponding values in (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X) and, (XI). In the anion, the Au Cl bond lengths and angles (Table 1) are normal. Intra and intermolecular C H Cl hydrogen bonding interactions (Table 2) stabilize the molecular conformation and the packing arrangement (Fig. 2). S2. Experimental A solution of 5,5 -dimethyl-2,2 -bipyridine (0.20 g, 1.09 mmol) in ethanol (20 ml) was added to a solution of HAuCl 3.3H 2 O, (0.37 g, 1.09 mmol) in acetonitrile (20 ml) and the resulting yellow solution was stirred for 10 min at 313 K. Then, it was left to evaporate slowly at room temperature. After one week, yellow prismatic crystals of (I) were isolated (yield 0.28 g, 72.8%; m.p. 553 K). S3. Refinement All H-atoms were placed in calculated positions with C H = 0.93 Å and C H 0.96 Å, and were included in the refinement in the riding model approximation, with U iso (H) = 1.2U eq (ring C) and U iso (H) = 1.5U eq (methyl C). In the final Fourier map, the highest and deepest peaks were located 0.91 and 0.81 Å from atom Au1, respectively. sup-1
4 Figure 1 The molecular structure of (I) showing 50% probability displacement ellipsoids for the non-hydrogen atoms. Symmetry code suffixes: (a) x, y, z; (b) 2 x, 1 y, 1 z. sup-2
5 Figure 2 A general view of the packing and hydrogen bonding interactions in (I). Bis[dichlorido(5,5 -dimethyl-2,2 -bipyridine-κ 2 N,N )gold(iii)] tetrachloridoaurate(iii) dichloridooaurate(i) Crystal data [AuCl 2 (C 12 H 12 N 2 )] 2 [AuCl 4 ][AuCl 2 ] M r = Triclinic, P1 Hall symbol: -P 1 a = (4) Å b = (4) Å c = (5) Å α = (4) β = (4) γ = (3) V = (7) Å 3 Z = 1 F(000) = 682 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from reflections θ = µ = mm 1 T = 295 K Prism, yellow mm sup-3
6 Data collection Stoe IPDS-2 diffractometer Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus Plane graphite monochromator Detector resolution: 6.67 pixels mm -1 ω scans Absorption correction: integration (X-RED32; Stoe & Cie, 2002) Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 191 parameters 0 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map T min = 0.054, T max = measured reflections 3651 independent reflections 3193 reflections with I > 2σ(I) R int = θ max = 26.5, θ min = 1.9 h = k = l = Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0703P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 1.64 e Å 3 Δρ min = 1.91 e Å 3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =KFc[ XFc 2 Λ 3 /sin(2θ)] -1/4 Extinction coefficient: (5) Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wr and all goodnesses of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The observed criterion of F 2 > σ(f 2 ) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Au (3) (3) (3) (1) Cl (3) (3) (3) (9) Cl (3) (3) (3) (9) N (9) (8) (7) (2) N (8) (7) (6) (19) C (11) (9) (9) (3) C (12) (10) (9) (3) C (11) (11) (10) (3) C (11) (11) (10) (3) C (11) (9) (8) (3) C (15) (11) (13) (4) C (10) (9) (8) (3) C (12) (11) (10) (3) C (13) (11) (11) (3) sup-4
7 C (13) (9) (10) (3) C (11) (9) (8) (3) C (14) (10) (12) (4) Au (2) Cl (5) (5) (5) (16) Cl (6) (3) (3) (12) Au (2) Cl (4) (3) (3) (7)* H * H * H * H6A * H6B * H6C * H * H * H * H12A * H12B * H12C * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Au (2) (2) (2) (1) (1) (1) Cl (14) (12) (19) (10) (13) (12) Cl (10) (13) (2) (9) (11) (13) N (3) (4) (4) (3) (3) (3) N (3) (3) (4) (3) (3) (3) C (5) (4) (6) (4) (4) (4) C (5) (5) (5) (4) (4) (4) C (5) (6) (6) (4) (4) (5) C (4) (5) (7) (4) (4) (5) C (4) (5) (5) (4) (4) (4) C (7) (6) (9) (5) (6) (6) C (4) (4) (5) (3) (3) (4) C (5) (5) (6) (4) (4) (5) C (6) (5) (7) (5) (5) (5) C (6) (4) (6) (4) (5) (4) C (5) (4) (5) (4) (4) (4) C (7) (5) (8) (4) (6) (5) Au (3) (3) (3) (2) (2) (2) Cl (2) (3) (3) (2) (2) (2) Cl (3) (12) (18) (15) (19) (11) Au (3) (3) (3) (2) (2) (2) sup-5
8 Geometric parameters (Å, º) Au1 N (9) C5 C (12) Au1 N (7) C7 C (15) Au1 Cl (3) C8 C (15) Au1 Cl (3) C9 C (18) Au2 Cl4 i (3) C10 C (15) Au2 Cl3 i (5) C10 C (14) Au2 Cl (5) C1 H Au2 Cl (3) C3 H Au3 Cl5 ii (3) C4 H Au3 Cl (3) C6 H6B N1 C (12) C6 H6A N1 C (13) C6 H6C N2 C (13) C8 H N2 C (11) C9 H C1 C (15) C11 H C2 C (16) C12 H12C C2 C (14) C12 H12A C3 C (15) C12 H12B C4 C (15) Au1 Cl3 iii (5) N1 C (12) Au1 Cl (3) N1 Cl (9) Au2 C7 iv (8) N2 Cl (9) Au2 C7 v (8) N2 N (10) Au3 C (9) N2 C (12) Au3 C1 ii (9) C1 Au (9) Cl1 Cl4 vi (4) C1 Au (9) Cl1 N (9) C3 Cl1 viii (12) Cl1 C (11) C5 Cl4 iv (9) Cl1 Cl (4) C6 Cl (14) Cl1 C3 vi (12) C7 Au2 iv (8) Cl2 N (9) C7 Au2 iii (8) Cl2 C (11) C8 Cl3 iv (12) Cl2 Cl (4) C10 Cl4 iii (11) Cl2 C11 vii (9) C11 Cl2 vii (9) Cl2 Cl5 vii (4) C12 C12 xi (15) Cl3 C (14) C4 H Cl3 C8 iv (12) C8 H Cl3 Cl (7) H1 Cl Cl3 Au1 v (5) H1 H6B Cl3 Cl4 i (7) H3 Cl1 viii Cl4 Cl3 i (7) H3 H6C Cl4 C10 v (11) H4 C Cl4 C5 iv (9) H4 Cl1 viii Cl4 Cl (7) H4 Cl2 viii Cl4 Cl1 viii (4) H4 H sup-6
9 Cl4 N1 iv (8) H6A Cl5 ii Cl5 Au (3) H6B H Cl5 Cl2 vii (4) H6B Cl3 ix Cl1 H4 vi H6C H Cl1 H H6C Cl Cl1 H3 vi H8 H Cl2 H8 vi H8 C Cl2 H H8 Cl2 viii Cl2 H4 vi H9 H12B Cl3 H6C H9 Cl5 x Cl3 H6B ix H11 Cl Cl5 H11 vii H11 H12C Cl5 H6A ii H11 Cl5 vii Cl5 H9 x H12B H N1 Cl4 iv (8) H12C H N1 N (10) Cl1 Au1 Cl (11) C7 C8 C (11) Cl1 Au1 N (2) C8 C9 C (11) Cl1 Au1 N (2) C11 C10 C (11) Cl2 Au1 N (2) C9 C10 C (9) Cl2 Au1 N (2) C9 C10 C (10) N1 Au1 N (3) N2 C11 C (10) Cl3 i Au2 Cl4 i (19) C2 C1 H Cl3 Au2 Cl4 i (19) N1 C1 H Cl3 Au2 Cl (19) C2 C3 H Cl3 Au2 Cl3 i C4 C3 H Cl3 i Au2 Cl (19) C3 C4 H Cl4 Au2 Cl4 i C5 C4 H Cl5 Au3 Cl5 ii C2 C6 H6A Au1 N1 C (7) C2 C6 H6B Au1 N1 C (6) C2 C6 H6C C1 N1 C (9) H6B C6 H6C Au1 N2 C (7) H6A C6 H6B Au1 N2 C (5) H6A C6 H6C C7 N2 C (8) C7 C8 H N1 C1 C (10) C9 C8 H C3 C2 C (11) C10 C9 H C1 C2 C (9) C8 C9 H C1 C2 C (10) N2 C11 H C2 C3 C (10) C10 C11 H C3 C4 C (10) C10 C12 H12A N1 C5 C (8) C10 C12 H12B N1 C5 C (9) C10 C12 H12C C4 C5 C (9) H12A C12 H12B N2 C7 C (8) H12A C12 H12C N2 C7 C (8) H12B C12 H12C C5 C7 C (9) sup-7
10 Cl1 Au1 N1 C1 3.4 (7) C11 N2 C7 C8 0.9 (12) N2 Au1 N1 C (8) N1 C1 C2 C3 1.7 (14) Cl1 Au1 N1 C (6) N1 C1 C2 C (10) N2 Au1 N1 C5 0.7 (6) C6 C2 C3 C (10) Cl2 Au1 N2 C (5) C1 C2 C3 C4 0.2 (15) N1 Au1 N2 C7 0.0 (6) C2 C3 C4 C5 2.1 (16) Cl2 Au1 N2 C (7) C3 C4 C5 C (9) N1 Au1 N2 C (7) C3 C4 C5 N1 2.2 (14) Au1 N1 C1 C (7) C4 C5 C7 N (8) C5 N1 C1 C2 1.7 (14) C4 C5 C7 C8 4.2 (15) Au1 N1 C5 C (7) N1 C5 C7 N2 1.2 (11) C1 N1 C5 C4 0.4 (13) N1 C5 C7 C (9) Au1 N1 C5 C7 1.2 (10) C5 C7 C8 C (9) C1 N1 C5 C (8) N2 C7 C8 C9 0.9 (14) Au1 N2 C11 C (7) C7 C8 C9 C (16) C7 N2 C11 C (13) C8 C9 C10 C (16) Au1 N2 C7 C (7) C8 C9 C10 C (10) Au1 N2 C7 C5 0.6 (9) C12 C10 C11 N (9) C11 N2 C7 C (7) C9 C10 C11 N2 1.3 (14) Symmetry codes: (i) x, y, z; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z; (iv) x+1, y+1, z; (v) x 1, y 1, z; (vi) x+1, y, z; (vii) x+3, y+2, z+1; (viii) x 1, y, z; (ix) x+1, y, z; (x) x+2, y+2, z+1; (xi) x+3, y+3, z+1. Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A C1 H1 Cl (11) 124 C8 H8 Cl2 viii (12) 169 C11 H11 Cl (11) 122 Symmetry code: (viii) x 1, y, z. sup-8
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