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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN b = (15) Å c = (14) Å = (6) V = (3) Å 3 Z =4 Mo K radiation = 1.34 mm 1 T = 299 (2) K mm Chlorido(ethyldiphenylphosphine-jP)- (1-pyrrolidinecarbodithioato-j 2 S,S 0 )- nickel(ii) Anna Kropidłowska, a * Ilona Turowska-Tyrk b and Barbara Becker a a Department of Inorganic Chemistry, Chemical Faculty, Gdańsk University of Technology, 11/12 G. Narutowicza St., PL Gdańsk, Poland, and b Institute of Physical and Theoretical Chemistry, Chemical Faculty, Wrocław University of Technology, 27 Wybrzeże Wyspiańskiego, PL Wrocław, Poland Correspondence anna@urethan.chem.pg.gda.pl Received 23 April 2008; accepted 24 April 2008 Key indicators: single-crystal X-ray study; T = 299 K; mean (C C) = Å; R factor = 0.040; wr factor = 0.114; data-to-parameter ratio = In the crystal structure of the title complex, [Ni(C 5 H 8 NS 2 )Cl- (C 14 H 15 P)], the Ni atom is coordinated by an S,S 0 -chelating dithiocarbamate, a chloride and a diphenylethylphosphine ligand in a distorted square-planar arrangement. Related literature For related literature, see: Allen (2002); Darkwa et al. (1999); Kropidłowska, Chojnacki et al. (2007); Kropidłowska, Janczak et al. (2007); Pastorek et al. (1996, 1999); Reger & Collins (1995). Experimental Crystal data [Ni(C 5 H 8 NS 2 )Cl(C 14 H 15 P)] M r = Monoclinic, P2 1 =c a = (5) Å Data collection Kuma KM-4-CCD diffractometer Absorption correction: refined from F (Walker & Stuart, 1983) T min = 0.553, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections measured reflections 3637 independent reflections 2989 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.57 e Å 3 min = 0.35 e Å 3 Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97. The authors acknowledge Professor J. Pikies for his donation of the sample of NiCl 2 (PPh 2 Et) 2 and J. Gołaszewska for her help during the crystallization. This work was supported by the Ministry of Science and Higher Education (Poland), grant No. 1 T09A A. Kropidłowska thanks the Foundation for Polish Science for a fellowship. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2563). References Allen, F. H. (2002). Acta Cryst. B58, Darkwa, J., Osei-Twum, E. Y. & Litrja, L. A. (1999). Polyhedron, 18, Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Kropidłowska, A., Chojnacki, J., Gołaszewska, J. & Becker, B. (2007). Acta Cryst. E63, m1643. Kropidłowska, A., Janczak, J., Gołaszewska, J. & Becker, B. (2007). Acta Cryst. E63, m1947. Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Poland, Wrocław, Poland. Pastorek, R., Trávníček, Z., Kvapilova, E., Šindelář, Z.& Březina, F. (1996). Polyhedron, 15, Pastorek, R., Trávníček, Z., Šindelář, Z.& Březina, F. (1999). Transition Met. Chem. 24, Reger, D. L. & Collins, J. E. (1995). Inorg. Chem. 34, Sheldrick, G. M. (2008). Acta Cryst. A64, Walker, N. & Stuart, D. (1983). Acta Cryst. A39, m748 Kropidłowska et al. doi: /s Acta Cryst. (2008). E64, m748
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3 Acta Cryst. (2008). E64, m748 [ doi: /s ] Chlorido(ethyldiphenylphosphine- P)(1-pyrrolidinecarbodithioato- 2 S,S')nickel(II) A. Kropidlowska, I. Turowska-Tyrk and B. Becker Comment Metal (Ni, Pd) complexes in which the atom is coordinated by a S,S-chelating dithiocarbamate, one halogenide and one phosphine have been investigated and used to obtain compounds with a sulfur rich kernel arising from the presence of two different S-donor ligands (Darkwa et al., 1999; Pastorek et al., 1999; Reger & Collins, 1995). Several structures of such species are stored in the Cambridge Structural Database (CSD-2007, Allen 2002). Recently, we reported the synthesis of [Ni{S 2 CN(CH 2 ) 4 }(Cl)(PPh 3 )] (Kropidłowska, Janczak et al., 2007) solvated by a chloroform molecule, which interacts with the complex by a weak C H S hydrogen bond. The structure of homologous hemisolvated [Ni{S 2 CN(CH 2 ) 4 }(Br)(PPh 3 )] has also been reported (Pastorek et al., 1996). In the present paper we describe the structure of another nickel(ii) complex - (1-pyrrolidinylcarbodithioato-S,S') -chlorido- (diphenylethylphosphine)nickel(ii), [Ni{S 2 CN(CH 2 ) 4 }(Cl)(PPh 2 Et)] (I) obtained by essentially quantitative metathesis of trans-dichloro-bis(diphenylethylphosphine)-nickel(ii) and bis(1-pyrrolidinylcarbodithioato-s,s')nickel(ii). The molecular structure of (I) with the atom numbering scheme is shown in Figure 1. In this compound the metal(ii) ion is four-coordinated within a typical square planar [NiClS 2 P] heterogeneous coordination sphere. The dithiocarbamate ligand acts as a bidentate chelate, coordinating to Ni via both S atoms and thus introducing a deformation of the coordination geometry. Atom S1 is located trans to the Cl ligand and atom S2 is trans to the diphenylethylphosphine ligand. Although (I) was obtained in the same manner as previously mentioned [Ni{S 2 CN(CH 2 ) 4 }(Cl)(PPh 3 )] it did not retain the solvent within its crystal structure, similarily to previously described [Ni{S 2 CN(C 4 H 8 O)}(Cl)(PPh 3 )] (Kropidłowska, Chojnacki et al., 2007). The schematic drawing of the crystal packing in (I) is presented in Figure 2. Experimental. Nickel chloride, NiCl 2 6H2 O (0.594 g, mol, purchased from POCh) was dissolved in 50 ml of methanol/water (10/1, v/v) and this solution was added dropwise to the ammonium salt of pyrrolidinylcarbodithioic acid C 4 H 8 NCS 2 NH 4 (0.82 g, mol, Fluka) dissolved in methanol/water. This mixture was stirred vigorously under argon atmosphere for ca 20 minutes, then filtered and the filtrate left for crystallization at 278 K. After a week the green crystalline product, namely Ni(S 2 CNC 4 H 8 ) 2 was collected. It was further dissolved (0.199 g, mol) in 10 ml of chloroform and mixed with solution of equimolar amount of NiCl 2 (PPh 2 Et) 2 (0.315 g). The mixture which turned into deep violet colour, was stirred for 10 minutes and then filtered. To the filtrate 10 ml of Et 2 O was added. After two days violet crystals were collected and washed with several portions of ether. sup-1
4 Refinement All H atoms were positioned geometrically and treated as riding with C H = Å, and with U iso (H) values of 1.2 U eq of the parent methylene carbon and U iso (H) values of 1.5xU eq of the methyl group carbon. Figures Fig. 1. Molecular structure and atom-numbering scheme for the title complex (I) with displacement ellipsoids drawn at 50% probability level. H atoms are represented as circles of arbitrary size. Fig. 2. Schematic drawing of the crystal packing down the a axis. Chlorido(ethyldiphenylphosphine-κP)(1-pyrrolidinecarbodithioato- κ 2 S,S')nickel(II) Crystal data [Ni(C 5 H 8 NS 2 )Cl(C 14 H 15 P)] F 000 = 944 M r = Monoclinic, P2 1 /c Hall symbol: -P 2ybc D x = Mg m 3 Mo Kα radiation λ = Å a = (5) Å θ = º b = (15) Å c = (14) Å β = (6)º V = (3) Å 3 Z = 4 Cell parameters from 3645 reflections µ = 1.34 mm 1 T = 299 (2) K Block, violet mm Data collection Kuma KM-4-CCD diffractometer Radiation source: fine-focus sealed tube Monochromator: graphite R int = T = 299(2) K θ max = 25.0º ω scans θ min = 3.1º 3637 independent reflections 2989 reflections with I > 2σ(I) sup-2
5 Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983) T min = 0.553, T max = h = 6 7 k = measured reflections l = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained wr(f 2 ) = w = 1/[σ 2 (F 2 o ) + (0.0634P) P] where P = (F 2 o + 2F 2 c )/3 S = 1.08 (Δ/σ) max = reflections Δρ max = 0.57 e Å parameters Δρ min = 0.35 e Å 3 Primary atom site location: structure-invariant direct methods Extinction correction: none Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness 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 threshold expression of F 2 > σ(f 2 ) is used only for calculating R- factors(gt) 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 Ni (6) (19) (2) (15) Cl (14) (4) (6) (3) P (11) (4) (5) (2) S (13) (5) (5) (2) S (13) (4) (5) (2) N (4) (14) (16) (7) C (4) (15) (17) (7) C (5) (17) (2) (8) H * C (7) (19) (2) (10) H * C (7) (2) (3) (11) H * sup-3
6 C (7) (2) (3) (11) H * C (5) (19) (2) (9) H * C (5) (16) (18) (7) C (6) (2) (2) (10) H * C (8) (2) (2) (12) H * C (8) (2) (2) (12) H * C (7) (3) (3) (13) H * C (5) (2) (2) (10) H * C (5) (19) (2) (9) H13A * H13B * C (6) (2) (3) (11) H14A * H14B * H14C * C (5) (17) (19) (7) C (7) (2) (2) (11) H16A * H16B * C (10) (3) (4) (2) H17A * H17B * C (7) (3) (3) (17) H18A * H18B * C (5) (2) (2) (9) H19A * H19B * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Ni (2) (2) (2) (16) (16) (16) Cl (6) (5) (6) (4) (4) (4) P (4) (4) (4) (3) (3) (3) S (5) (5) (5) (4) (4) (4) S (5) (5) (5) (4) (4) (4) N (16) (16) (15) (13) (13) (13) C (16) (17) (15) (13) (12) (13) C (19) (19) (18) (16) (15) (15) C (3) (2) (2) (19) (2) (17) sup-4
7 C (3) (2) (3) (2) (2) (19) C (2) (3) (3) (2) (2) (2) C (2) (2) (2) (16) (16) (16) C (17) (17) (16) (13) (13) (13) C (2) (2) (2) (19) (17) (18) C (4) (3) (2) (3) (2) (2) C (3) (3) (2) (3) (2) (2) C (3) (4) (3) (2) (2) (3) C (19) (3) (2) (18) (16) (19) C (19) (2) (2) (16) (16) (18) C (2) (2) (3) (18) (2) (2) C (17) (18) (17) (14) (13) (14) C (3) (2) (2) (2) (2) (2) C (5) (4) (5) (4) (4) (4) C (3) (4) (4) (3) (3) (3) C (19) (2) (2) (17) (16) (18) Geometric parameters (Å, ) Ni1 S (9) C8 H Ni1 Cl (9) C9 C (6) Ni1 P (8) C9 H Ni1 S (9) C10 C (6) P1 C (3) C10 H P1 C (3) C11 C (5) P1 C (3) C11 H S1 C (3) C12 H S2 C (3) C13 C (5) N1 C (4) C13 H13A N1 C (5) C13 H13B N1 C (4) C14 H14A C1 C (4) C14 H14B C1 C (4) C14 H14C C2 C (5) C16 C (6) C2 H C16 H16A C3 C (6) C16 H16B C3 H C17 C (7) C4 C (6) C17 H17A C4 H C17 H17B C5 C (5) C18 C (5) C5 H C18 H18A C6 H C18 H18B C7 C (5) C19 H19A C7 C (5) C19 H19B C8 C (5) S1 Ni1 Cl (4) C9 C10 H S1 Ni1 P (3) C10 C11 C (4) Cl1 Ni1 P (3) C10 C11 H S1 Ni1 S (3) C12 C11 H sup-5
8 Cl1 Ni1 S (4) C7 C12 C (4) P1 Ni1 S (4) C7 C12 H C1 P1 C (14) C11 C12 H C1 P1 C (16) C14 C13 P (3) C7 P1 C (16) C14 C13 H13A C1 P1 Ni (9) P1 C13 H13A C7 P1 Ni (10) C14 C13 H13B C13 P1 Ni (14) P1 C13 H13B C15 S1 Ni (11) H13A C13 H13B C15 S2 Ni (11) C13 C14 H14A C15 N1 C (3) C13 C14 H14B C15 N1 C (3) H14A C14 H14B C16 N1 C (3) C13 C14 H14C C2 C1 C (3) H14A C14 H14C C2 C1 P (2) H14B C14 H14C C6 C1 P (2) N1 C15 S (2) C3 C2 C (3) N1 C15 S (2) C3 C2 H S2 C15 S (18) C1 C2 H C17 C16 N (3) C4 C3 C (4) C17 C16 H16A C4 C3 H N1 C16 H16A C2 C3 H C17 C16 H16B C5 C4 C (4) N1 C16 H16B C5 C4 H H16A C16 H16B C3 C4 H C18 C17 C (4) C4 C5 C (4) C18 C17 H17A C4 C5 H C16 C17 H17A C6 C5 H C18 C17 H17B C5 C6 C (4) C16 C17 H17B C5 C6 H H17A C17 H17B C1 C6 H C17 C18 C (4) C12 C7 C (3) C17 C18 H18A C12 C7 P (3) C19 C18 H18A C8 C7 P (3) C17 C18 H18B C9 C8 C (4) C19 C18 H18B C9 C8 H H18A C18 H18B C7 C8 H N1 C19 C (3) C10 C9 C (4) N1 C19 H19A C10 C9 H C18 C19 H19A C8 C9 H N1 C19 H19B C11 C10 C (4) C18 C19 H19B C11 C10 H H19A C19 H19B sup-6
9 Fig. 1 sup-7
10 Fig. 2 sup-8
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