metal-organic compounds
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- Δελφινιος Μανιάκης
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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Triethylammonium bis(oxalato)- oxido(triphenylphosphane)rhenate(v) Philipp Grimminger and Peter Klüfers* Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstrasse 5 13, München, Germany Correspondence kluef@cup.uni-muenchen.de b = (2) Å c = (5) Å V = (15) Å 3 Z =8 Data collection Nonius KappaCCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T min = 0.631, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections Mo K radiation = 4.31 mm 1 T = 200 (2) K mm measured reflections 6646 independent reflections 3895 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 1.08 e Å 3 min = 0.57 e Å 3 Received 9 November 2007; accepted 21 November 2007 Key indicators: single-crystal X-ray study; T = 200 K; mean (C C) = Å; R factor = 0.033; wr factor = 0.079; data-to-parameter ratio = The anionic part of the title compound, (C 6 H 16 N)- [Re(C 2 O 4 ) 2 O(C 18 H 15 P)], is a substituted derivative of transtrichloridooxidobis(triphenylphosphane)rhenium(v) with oxalate. In the structure of the anion, an oxidorhenium(v) unit defines a molecular axis in a distorted octahedral coordination about the central atom. The second axial position is occupied by an O atom of one of the chelating oxalate ligands. The distances of the oxalate O atoms to the central Re atom vary from (3) to (3) Å, the longest bond being the one trans to the oxide ligand. The anions and cations are connected by a bifurcated hydrogen bond from a triethylammonium NH donor to two oxalate O-atom acceptors. Related literature The title compound was synthesized by analogy with a published procedure (Kettler et al., 1994). For the crystal structure of a related compound with oxalate as the ligand, see: Chiozzone et al. (2001). Experimental Crystal data (C 6 H 16 N)[Re(C 2 O 4 ) 2 O(C 18 H 15 P)] M r = Orthorhombic, Pbca a = (2) Å Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA N H71O (5) 140 N H71O (5) 136 Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: SHELXL97. The authors thank Dr Peter Mayer for professional support and Richard Betz for helpful discussions. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2113). References 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, Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL Oak Ridge National Laboratory, Tennessee, USA. Chiozzone, R., González, R., Kremer, C., De Munno, G. & Faus, J. (2001). Inorg. Chim. Acta, 325, Keller, E. (1999). SCHAKAL99. Universität Freiburg, Freiburg, Germany. Kettler, P. B., Chang, Y. D. & Zubieta, J. (1994). Inorg. Chim. Acta, 218, Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp New York: Academic Press. Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Sheldrick, G. M. (2001). SADABS. Version 2. University of Göttingen, Germany. m3188 # 2007 International Union of Crystallography doi: /s Acta Cryst. (2007). E63, m3188
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3 Acta Cryst. (2007). E63, m3188 [ doi: /s ] Triethylammonium bis(oxalato)oxido(triphenylphosphane)rhenate(v) P. Grimminger and P. Klüfers Comment The title compound (I) was prepared as a precursor in a study on hydrolytically stable rhenium(v) compounds. Fig. 1 shows the anion with its two chelating oxalato ligands. The anion's charge is counterbalanced by a triethylammonium cation. In the crystal structure, hydrogen bonds are formed between non-re-bonded O32 and O42 atoms of one of the oxalato ligands and the protonated triethylamine (Fig. 2). Experimental The title compound was prepared in analogy to a published procedure (Kettler et al., 1994) g (1.0 mmol) of the rhenium(v)-oxo-complex trans-reocl3(pph3)2 was stirred with g (4.0 mmol) oxalic acid and g (4.0 mmol) triethylamine in 100 ml me thanol for 3 h at 60 C. Then the volume was reduced in vacuo to 20 ml. Violet crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the compound in methanol at room temperature. Refinement All H atoms were located in a difference map and refined as riding on their parent atoms. One common isotropic displacement parameter for all H atoms was refined. Figures Fig. 1. The structure of ion pairs in (I), with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-h atoms. Hydrogen bonds are indicated by dotted lines. Fig. 2. The packing of (I), viewed along [1 0 0]. sup-1
4 Triethylammonium bis(oxalato)oxido(triphenylphosphane)rhenate(v) Crystal data (C 6 H 16 N)[Re(C 2 O 4 ) 2 O(C 18 H 15 P)] F 000 = 2944 M r = Orthorhombic, Pbca Hall symbol: -P 2ac 2ab D x = Mg m 3 Mo Kα radiation λ = Å a = (2) Å θ = º b = (2) Å c = (5) Å V = (15) Å 3 Z = 8 Cell parameters from 7243 reflections µ = 4.31 mm 1 T = 200 (2) K Block, blue mm Data collection Nonius KappaCCD diffractometer Radiation source: rotating anode Monochromator: MONTEL, graded multilayered X- ray optics 6646 independent reflections 3895 reflections with I > 2σ(I) R int = T = 200(2) K θ max = 27.7º CCD; rotation images; thick slices scans θ min = 3.2º Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T min = 0.631, T max = h = k = measured reflections l = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o 2 ) + (0.0284P) P] where P = (F o 2 + 2F c 2 )/3 S = 1.02 (Δ/σ) max = reflections Δρ max = 1.08 e Å parameters Δρ min = 0.57 e Å 3 Primary atom site location: structure-invariant direct methods Extinction correction: none Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq sup-2
5 Re (15) (10) (5) (7) O (2) (17) (11) (8) C (4) (3) (16) (11) C (4) (3) (16) (12) C (4) (3) (15) (11) C (4) (3) (14) (11) O (2) (19) (10) (8) O (3) (2) (11) (9) O (2) (18) (10) (8) O (3) (3) (14) (13) O (2) (18) (10) (7) O (3) (2) (11) (9) O (2) (18) (9) (7) O (3) (19) (10) (8) P (9) (7) (4) (3) C (3) (3) (14) (10) C (4) (3) (15) (11) H (3)* C (4) (3) (16) (13) H (3)* C (5) (3) (17) (15) H (3)* C (4) (3) (16) (13) H (3)* C (4) (3) (15) (12) H (3)* C (3) (3) (14) (10) C (4) (3) (17) (12) H (3)* C (5) (3) (19) (16) H (3)* C (5) (4) (2) (16) H (3)* C (5) (3) (18) (16) H (3)* C (4) (3) (15) (13) H (3)* C (4) (3) (14) (10) C (4) (3) (14) (11) H (3)* C (4) (3) (15) (13) H (3)* C (4) (3) (16) (14) H (3)* C (5) (3) (16) (13) H (3)* C (4) (3) (14) (11) H (3)* N (3) (2) (12) (10) sup-3
6 H (3)* C (4) (3) (16) (12) H (3)* H (3)* C (4) (4) (17) (15) H (3)* H (3)* H (3)* C (4) (3) (16) (13) H (3)* H (3)* C (4) (4) (18) (16) H (3)* H (3)* H (3)* C (4) (4) (17) (15) H (3)* H (3)* C (5) (3) (18) (16) H (3)* H (3)* H (3)* Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Re (10) (9) (11) (9) (10) (7) O (2) (15) (19) (16) (18) (14) C (3) (3) (3) (2) (3) (2) C (3) (3) (3) (2) (2) (2) C (3) (3) (3) (2) (2) (2) C (3) (2) (3) (2) (2) (2) O (18) (19) (2) (14) (15) (16) O (2) (2) (2) (17) (18) (18) O (2) (17) (18) (15) (15) (14) O (3) (3) (3) (2) (2) (3) O (18) (17) (19) (14) (15) (14) O (2) (2) (2) (17) (17) (18) O (19) (16) (16) (12) (13) (13) O (2) (19) (19) (16) (16) (15) P (7) (5) (6) (5) (5) (5) C (3) (2) (2) (18) (19) (2) C (3) (3) (3) (2) (2) (2) C (3) (3) (3) (2) (3) (2) C (4) (3) (3) (3) (3) (2) C (3) (3) (3) (3) (3) (3) C (3) (3) (3) (2) (2) (2) C (3) (2) (3) (19) (2) (2) sup-4
7 C (3) (3) (3) (3) (3) (2) C (4) (3) (4) (3) (3) (3) C (4) (3) (4) (3) (3) (3) C (4) (3) (3) (3) (3) (3) C (4) (3) (3) (3) (2) (2) C (3) (2) (3) (2) (2) (2) C (3) (2) (3) (2) (2) (2) C (3) (3) (3) (2) (2) (3) C (4) (3) (3) (3) (3) (3) C (4) (3) (3) (3) (3) (2) C (3) (2) (3) (2) (2) (2) N (2) (2) (2) (19) (18) (19) C (3) (3) (3) (2) (2) (2) C (3) (4) (3) (3) (3) (3) C (3) (3) (3) (2) (2) (3) C (4) (4) (3) (3) (3) (3) C (3) (4) (3) (3) (3) (3) C (4) (4) (4) (3) (3) (3) Geometric parameters (Å, ) Re O (3) C14 H Re O (3) C15 C (6) Re O (3) C15 H Re O (3) C16 H Re O (3) C17 C (6) Re P (11) C17 C (6) C1 O (5) C18 C (6) C1 O (5) C18 H C1 C (6) C19 C (7) C2 O (5) C19 H C2 O (5) C20 C (7) C3 O (5) C20 H C3 O (5) C21 C (6) C3 C (6) C21 H C4 O (5) C22 H C4 O (5) N C (6) P C (4) N C (5) P C (4) N C (6) P C (4) N H C5 C (6) C23 C (7) C5 C (6) C23 H C6 C (6) C23 H C6 H C24 H C7 C (8) C24 H C7 H C24 H C8 C (7) C25 C (6) C8 H C25 H C9 C (6) C25 H sup-5
8 C9 H C26 H C10 H C26 H C11 C (6) C26 H C11 C (6) C27 C (7) C12 C (7) C27 H C12 H C27 H C13 C (7) C28 H C13 H C28 H C14 C (7) C28 H O1 Re O (14) C14 C15 C (5) O1 Re O (14) C14 C15 H O11 Re O (12) C16 C15 H O1 Re O (13) C11 C16 C (5) O11 Re O (13) C11 C16 H O21 Re O (12) C15 C16 H O1 Re O (13) C18 C17 C (4) O11 Re O (12) C18 C17 P (3) O21 Re O (12) C22 C17 P (4) O31 Re O (11) C19 C18 C (4) O1 Re P (10) C19 C18 H O11 Re P (9) C17 C18 H O21 Re P (9) C18 C19 C (5) O31 Re P (9) C18 C19 H O41 Re P (8) C20 C19 H O12 C1 O (4) C21 C20 C (5) O12 C1 C (4) C21 C20 H O11 C1 C (4) C19 C20 H O22 C2 O (5) C20 C21 C (5) O22 C2 C (5) C20 C21 H O21 C2 C (4) C22 C21 H O32 C3 O (4) C21 C22 C (5) O32 C3 C (4) C21 C22 H O31 C3 C (4) C17 C22 H O42 C4 O (4) C27 N C (4) O42 C4 C (4) C27 N C (4) O41 C4 C (4) C23 N C (4) C1 O11 Re (3) C27 N H C2 O21 Re (3) C23 N H C3 O31 Re (3) C25 N H C4 O41 Re (3) C24 C23 N (4) C5 P C (2) C24 C23 H C5 P C (19) N C23 H C17 P C (2) C24 C23 H C5 P Re (14) N C23 H C17 P Re (14) H231 C23 H C11 P Re (15) C23 C24 H C10 C5 C (4) C23 C24 H C10 C5 P (3) H241 C24 H C6 C5 P (3) C23 C24 H sup-6
9 C7 C6 C (5) H241 C24 H C7 C6 H H242 C24 H C5 C6 H C26 C25 N (4) C6 C7 C (5) C26 C25 H C6 C7 H N C25 H C8 C7 H C26 C25 H C7 C8 C (5) N C25 H C7 C8 H H251 C25 H C9 C8 H C25 C26 H C8 C9 C (5) C25 C26 H C8 C9 H H261 C26 H C10 C9 H C25 C26 H C5 C10 C (4) H261 C26 H C5 C10 H H262 C26 H C9 C10 H N C27 C (4) C16 C11 C (4) N C27 H C16 C11 P (3) C28 C27 H C12 C11 P (4) N C27 H C13 C12 C (5) C28 C27 H C13 C12 H H271 C27 H C11 C12 H C27 C28 H C14 C13 C (5) C27 C28 H C14 C13 H H281 C28 H C12 C13 H C27 C28 H C15 C14 C (5) H281 C28 H C15 C14 H H282 C28 H C13 C14 H O12 C1 C2 O (8) O41 Re P C (17) O11 C1 C2 O (5) C17 P C5 C (4) O12 C1 C2 O (5) C11 P C5 C (4) O11 C1 C2 O (6) Re P C5 C (4) O32 C3 C4 O (7) C17 P C5 C (3) O31 C3 C4 O (4) C11 P C5 C (4) O32 C3 C4 O (4) Re P C5 C (4) O31 C3 C4 O (5) C10 C5 C6 C7 1.0 (7) O12 C1 O11 Re (4) P C5 C6 C (4) C2 C1 O11 Re 6.9 (5) C5 C6 C7 C8 1.0 (7) O1 Re O11 C (3) C6 C7 C8 C9 2.6 (8) O21 Re O11 C1 9.1 (3) C7 C8 C9 C (8) O31 Re O11 C (5) C6 C5 C10 C9 1.5 (7) O41 Re O11 C (3) P C5 C10 C (3) P Re O11 C (3) C8 C9 C10 C5 0.1 (7) O22 C2 O21 Re (5) C5 P C11 C (4) C1 C2 O21 Re 8.9 (5) C17 P C11 C (4) O1 Re O21 C (3) Re P C11 C (3) O11 Re O21 C2 9.9 (3) C5 P C11 C (4) O31 Re O21 C (3) C17 P C11 C (4) O41 Re O21 C (3) Re P C11 C (4) P Re O21 C (5) C16 C11 C12 C (7) sup-7
10 O32 C3 O31 Re (4) P C11 C12 C (4) C4 C3 O31 Re 7.1 (5) C11 C12 C13 C (8) O1 Re O31 C (3) C12 C13 C14 C (9) O11 Re O31 C (5) C13 C14 C15 C (9) O21 Re O31 C (3) C12 C11 C16 C (7) O41 Re O31 C3 5.7 (3) P C11 C16 C (4) P Re O31 C (3) C14 C15 C16 C (8) O42 C4 O41 Re (3) C5 P C17 C (4) C3 C4 O41 Re 0.2 (5) C11 P C17 C (3) O1 Re O41 C (7) Re P C17 C (4) O11 Re O41 C (3) C5 P C17 C (3) O21 Re O41 C (3) C11 P C17 C (4) O31 Re O41 C4 2.8 (3) Re P C17 C (3) P Re O41 C (3) C22 C17 C18 C (6) O1 Re P C (18) P C17 C18 C (3) O11 Re P C (18) C17 C18 C19 C (7) O21 Re P C (4) C18 C19 C20 C (7) O31 Re P C (17) C19 C20 C21 C (7) O41 Re P C (17) C20 C21 C22 C (7) O1 Re P C (19) C18 C17 C22 C (6) O11 Re P C (18) P C17 C22 C (3) O21 Re P C (4) C27 N C23 C (4) O31 Re P C (18) C25 N C23 C (5) O41 Re P C (17) C27 N C25 C (5) O1 Re P C (19) C23 N C25 C (6) O11 Re P C (18) C23 N C27 C (5) O21 Re P C (4) C25 N C27 C (4) O31 Re P C (18) Hydrogen-bond geometry (Å, ) D H A D H H A D A D H A N H71 O (5) 140 N H71 O (5) 136 sup-8
11 Fig. 1 sup-9
12 Fig. 2 sup-10
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