1,3-Bis(2-thienylmeth­yl)-4,5-dihydro­imidazolium trichlorido(η6-p-cymene)ruthenate(II)

Arslan, H.; VanDerveer, D.; Özdemir, İ.; Gürbüz, N.; Gök, Y.; Çetinkaya, B.

doi:10.1107/S1600536809000464

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages m165-m166

doi:10.1107/S1600536809000464

Open

access

1,3-Bis(2-thienylmethyl)-4,5-dihydroimidazolium trichlorido(η⁶-p-cymene)ruthenate(II)

Hakan Arslan,^a,^b ^* Don VanDerveer,^c İsmail Özdemir,^d Nevin Gürbüz,^d Yetkin Gök ^d and Bekir Çetinkaya ^e

^aDepartment of Natural Sciences, Fayetteville State University, Fayetteville, NC 28301, USA, ^bDepartment of Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR 33169, Turkey, ^cDepartment of Chemistry, Clemson University, Clemson, SC 29634, USA, ^dDepartment of Chemistry, Faculty of Science and Arts, İnönü University, Malatya, TR 44280, Turkey, and ^eDepartment of Chemistry, Faculty of Science, Ege University, Bornova-İzmir, TR 35100, Turkey
^*Correspondence e-mail: hakan.arslan.acad@gmail.com

(Received 1 January 2009; accepted 6 January 2009; online 10 January 2009)

The asymmetric unit of the title compound, (C₁₃H₁₅N₂S₂)[RuCl₃(C₁₀H₁₄)], contains a 1,3-(2-thienylmethyl)-4,5-dihydroimidazolium cation and a trichlorido(η⁶-p-cymene)ruthenate(II) anion. The thiophene rings of the cation are disordered by an 180° rotation about the thiophene–CH₂ bonds with occupancies of 0.847 (5)/0.153 (5) and 0.700 (5)/0.300 (5), respectively. The Ru atom exhibits a distorted octahedral coordination with the benzene ring of the p-cymene ligand formally occupying three sites and three Cl atoms occupying the other three sites. The short C—N bond lengths in the imidazoline ring indicate partial electron delocalization within the N—C—N fragment. Cation and anions are connected through five intermolecular C—H⋯Cl hydrogen bonds and one C—H⋯π hydrogen bond, forming a three-dimensional hydrogen-bonded network.

Related literature

For the synthesis, see: Yaşar et al. (2008 ). Özdemir et al. (2008 , 2007 , 2005 ). For general background, see: Herrmann et al. (1995 ); Herrmann (2002 ); Arduengo & Krafczyc (1998 ). For related compounds, see: Arslan et al. (2007 , 2005a ,b ) and references therein; Sonar et al. (2004 , 2005a ,b ); Wagner et al. (2006a ,b ); Crundwell et al. (2002 ); Linehan et al. (2003 ); Liu et al. (2004 ); Navarro et al. (2006 ); Therrien et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

(C₁₃H₁₅N₂S₂)[RuCl₃(C₁₀H₁₄)]
M_r = 605.02
Triclinic, $[P \overline 1]$
a = 9.910 (2) Å
b = 11.600 (2) Å
c = 12.659 (3) Å
α = 84.95 (3)°
β = 67.05 (3)°
γ = 74.14 (3)°
V = 1288.8 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.10 mm⁻¹
T = 153 (2) K
0.48 × 0.19 × 0.17 mm

Data collection

Rigaku AFC-8S Mercury CCD diffractometer
Absorption correction: multi-scan (REQUAB; Jacobson, 1998 ) T_min = 0.621, T_max = 0.836
11095 measured reflections
4557 independent reflections
4062 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.084
S = 1.13
4557 reflections
285 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cl1ⁱ	0.96	2.62	3.450 (4)	144
C14—H14A⋯Cl1ⁱ	0.96	2.82	3.553 (4)	134
C19—H19A⋯Cl2ⁱ	0.96	2.81	3.671 (4)	150
C23—H23⋯Cl1ⁱⁱ	0.96	2.66	3.549 (4)	154
C14—H14B⋯Cg2ⁱⁱⁱ	0.96	2.83	3.784 (5)	171
C19—H19B⋯Cl1	0.96	2.86	3.759 (5)	157
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x, -y+2, -z+2; (iii) -x+1, -y+1, -z+2. Cg1 is the centroid of the S2,C20–C23 thiophene ring.

Data collection: CrystalClear (Rigaku/MSC, 2006 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000464/hg2465sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000464/hg2465Isup2.hkl

checkCIF report

Comment top

Metal-carbene compounds, such as N-heterocyclic carbene palladium and ruthenium complexes, are important catalysts that have a wide range of applications such as Suzuki-Miyaura, Sonogashira, Stille and Heck reactions (Herrmann 2002; Herrmann et al., 1995; Navarro et al., 2006; Arduengo & Krafczyc, 1998).

In previous papers, we have described the synthesis, characterization and applications of palladium, platinum and ruthenium N-heterocyclic carbene complexes as catalysts (Yaşar et al., 2008; Arslan et al., 2007, 2005a, 2005b, and references therein; Özdemir et al., 2008, 2007, 2005, and references therein). In view of these important attributes of N-heterocyclic carbene derivatives, we report here the crystal structure of one of them. The title compound consists 1,3-bis(thiophen-2-ylmethyl)-4,5-dihydro-1H-imidazolium cation and a trichloro(η⁶-p-cymene) ruthenium(II) anion. The molecular structure of the title compound, (I), is depicted in Fig. 1. Cation and anion groups are connected with five intermolecular C—H···Cl hydrogen bonds and one C—H···π hydrogen bond, forming a three-dimensional hydrogen-bonding network (Fig. 2).

A flip disorder of both thiophene rings in 1,3-bis(thiophen-2-ylmethyl)-4,5-dihydro-1H-imidazolium cation is observed. There are two positions of both thiophene rings, rotated by 180°. The crystal structure of the cation contains four disordered atoms, S1, S2, C16, and C21. The site occupancy factors refined to 0.847 (5) and 0.153 (5) for the S1—C15—C16—C17—C18 ring, and 0.700 (5) and 0.300 (5) for the S2—C20—C21—C22—C23 ring. A similar thiophene ring disorder has been observed in some thiophene derivatives, such as (Z)-3-(1-methyl-1H-indol-3-yl)-2-(thiophen-3-yl)acrylonitrile (Sonar et al., 2004), (Z)-2-(3-thienyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile (Sonar et al., 2005a), (Z)-3-(1H-Indol-3-yl)-2-(3-thienyl)acrylonitrile and (Z)-3-[1-(4-tert-butylbenzyl)-1H-indol-3-yl]-2-(3-thienyl)acrylonitrile (Sonar et al., 2005b), 1,2-di-3-thienyl-2-hydroxyethanone(3,3-thenoin) (Crundwell et al., 2002), 3-[2-(anthracen-9-yl)ethenyl] thiophene, (Wagner et al., 2006a), 2,5-bis(2-cyano-2-thienylvinyl)thiophene (Wagner et al., 2006b), and 1,4-diphenyl-2,3-dithien-3-ylcyclopentadien-1-one (Linehan et al., 2003). In addition, all thiophene rings in the cation are almost planar; the maximum deviations from the least squares planes are 0.019 (4)Å for C16 and 0.006 (6)Å for C22.

The coordination geometry of ruthenium is pseudooctahedral, with an average Ru—Cl bond distance of 2.430Å. The ruthenium atom exhibits a distorted octahedral coordination with the benzene ring of the p-cymene ligand formally occupying three sites and three chloride atoms occupying other three sites. The distance between the centroid of the p-cymene ring and ruthenium is 1.6493 (15) Å, which is longer than that reported in other ruthenium compounds (Liu et al., 2004; Therrien et al., 2004). All the other bond lengths in (I) are in normal ranges (Allen et al., 1987).

The imidazolidine ring is almost planar, the deviations from planarity of ring are N1 0.002 (3), C11 0.001 (4), N2 0.004 (3), C12 0.005 (4), C13 0.004 (4)Å. The some C—N bond lengths (N1—C11 = 1.307 (4)Å and N2—C11 = 1.302 (4)Å) for the imidazolidine ring are shorter than the average single C—N bond length of 1.48Å, thus showing double bond character in these C—N bonds. The other CN bonds length (N1—C13 1.458 (5), N1—C14 1.462 (4), N2—C19 1.460 (4) and N2—C12 1.466 (4)Å) is agree with 1.48Å C—N single bond lengths. This information indicates a partial electron delocalization within the N1—C11—N2 fragment.

The crystal packing is shown in Fig. 2. Five intermolecular C—H···Cl hydrogen bonds link the molecules of (I) and generate a three-dimensional hydrogen bonded framework. In addition, a C14 (x, y, z)-H···π (S2—C20—C21—C22—C23, thiophene ring; 1 - x, 1 - y, 2 - z) hydrogen bond is observed in the title compound, Table 1.

Related literature top

For the synthesis, see: Yaşar et al. (2008). Özdemir et al. (2008, 2007, 2005). For general background, see: Herrmann et al. (1995); Herrmann (2002); Arduengo & Krafczyc (1998). For related compounds, see: Arslan et al. (2007, 2005a,b) and references therein; Sonar et al. (2004, 2005a,b); Wagner et al. (2006a,b); Crundwell et al. (2002); Linehan et al. (2003); Liu et al. (2004); Navarro et al. (2006); Therrien et al. (2004). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the S2,C20–C23 thiophene ring.

Experimental top

A suspension of 1,3-bis(thiophen-2ylmethyl)-,4,5-dihydro-1H-imidazolium chloride (1.1 mmol), Cs₂CO₃(1.2 mmol) and [RuCl₂(p-cymene)] (0.5 mmol) was heated under reflux in degassed toluene (20 ml) for 7 h (Fig. 3). The reaction mixture was then filtered while hot, and the volume was reduced to about 10 ml before addition of n-hexane (15 ml). The precipitate formed was crystallized from CH₂Cl₂: hexane (5:10 ml) to give the complex as red-brown crystals. Yields: 0.208 g, 69%. M.p.: 227–228°C. ¹H NMR(CDCl₃) δ: 1.39 (d, 6H, J = 6.9 Hz, CH₃(C₆H₄)CH(CH₃)₂), 2.29 (s, 3H, CH₃(C₆H₄)CH(CH₃)₂), 3.21 (m, 1H, CH₃(C₆H₄)CH(CH₃)₂)_,3.79 (s, 4H, NCH₂CH₂N), 4.12 (s, 4H, CH₂C₄H₃S), 5.29 and 5.58 (d, 4H, J = 5.8 Hz, CH₃(C₆H₄)CH(CH₃)₂), 7.03–7.68 (m, 6H, C₄H₃S), 8.99 (s, 1H, 2-CH). ¹³C NMR (CDCl₃) δ: 18.6 (CH₃(C₆H₄)CH(CH₃)₂), 22.3 (CH₃(C₆H₄)CH(CH₃)₂), 30.8 (CH₃(C₆H₄)CH(CH₃)₂), 47.0 (NCH₂CH₂N), 47.1 (CH₂C₄H₃S), 79.6, 81.8, 96.5 and 100.8 (CH₃(C₆H₄)CH(CH₃)₂), 126.7, 127.5, 129.1 and 135.2 (C₄H₃S), 159.3 (2-CH). Anal. Calc. for C₂₃H₂₉S₂N₂RuCl₃: C, 45.66; H, 4.83; N, 4.63%. Found: C, 45.71; H, 4.89; N, 4.69%.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). Symmetry: H19I, H14I, H11D, -x, 1 - y, 2 - z; H23A, -x, 2 - y, 2 - z; H23C, 1 + x, -1 + y, -1 + z; H19K, H14K, H11E, 1 + x, y,-1 + z; H19F, Cl1A, Cl2A, 1 - x,1 - y,1 - z.
	Fig. 3. Synthesis of the title compound.

1,3-Bis(2-thienylmethyl)-4,5-dihydroimidazolium trichlorido(η⁶-p-cymene)ruthenate(II) top

Crystal data top

(C₁₃H₁₅N₂S₂)[RuCl₃(C₁₀H₁₄)]	Z = 2
M_r = 605.02	F(000) = 616
Triclinic, P1	D_x = 1.559 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.910 (2) Å	Cell parameters from 5195 reflections
b = 11.600 (2) Å	θ = 3.3–26.4°
c = 12.659 (3) Å	µ = 1.10 mm⁻¹
α = 84.95 (3)°	T = 153 K
β = 67.05 (3)°	Rod, red
γ = 74.14 (3)°	0.48 × 0.19 × 0.17 mm
V = 1288.8 (6) Å³

Data collection top

Rigaku AFC-8S Mercury CCD diffractometer	4557 independent reflections
Radiation source: Sealed Tube	4062 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.019
Detector resolution: 14.6306 pixels mm^-1	θ_max = 25.2°, θ_min = 3.3°
ω scans	h = −11→11
Absorption correction: multi-scan (Jacobson, 1998)	k = −11→13
T_min = 0.621, T_max = 0.836	l = −15→15
11095 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0406P)² + 0.9404P] where P = (F_o² + 2F_c²)/3
4557 reflections	(Δ/σ)_max = 0.001
285 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

(C₁₃H₁₅N₂S₂)[RuCl₃(C₁₀H₁₄)]	γ = 74.14 (3)°
M_r = 605.02	V = 1288.8 (6) Å³
Triclinic, P1	Z = 2
a = 9.910 (2) Å	Mo Kα radiation
b = 11.600 (2) Å	µ = 1.10 mm⁻¹
c = 12.659 (3) Å	T = 153 K
α = 84.95 (3)°	0.48 × 0.19 × 0.17 mm
β = 67.05 (3)°

Data collection top

Rigaku AFC-8S Mercury CCD diffractometer	4557 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	4062 reflections with I > 2σ(I)
T_min = 0.621, T_max = 0.836	R_int = 0.019
11095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.13	Δρ_max = 0.43 e Å⁻³
4557 reflections	Δρ_min = −0.68 e Å⁻³
285 parameters

Special details top

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ru1	−0.02777 (3)	0.69238 (2)	0.639788 (19)	0.03323 (9)
Cl1	−0.10558 (9)	0.78990 (7)	0.82284 (6)	0.04448 (19)
Cl2	0.08996 (10)	0.51572 (7)	0.72233 (7)	0.04740 (19)
Cl3	−0.26047 (9)	0.62550 (8)	0.71790 (7)	0.0506 (2)
C1	0.1893 (4)	0.7262 (3)	0.5295 (3)	0.0484 (8)
C2	0.1573 (4)	0.6370 (3)	0.4777 (3)	0.0462 (8)
H2	0.2310	0.5610	0.4550	0.055*
C3	0.0226 (4)	0.6570 (4)	0.4593 (3)	0.0512 (8)
H3	0.0058	0.5957	0.4235	0.061*
C4	−0.0892 (4)	0.7679 (4)	0.4935 (3)	0.0534 (9)
C5	−0.0618 (5)	0.8573 (3)	0.5467 (3)	0.0559 (9)
H5	−0.1363	0.9327	0.5705	0.067*
C6	0.0761 (4)	0.8346 (3)	0.5644 (3)	0.0510 (8)
H6	0.0924	0.8953	0.6015	0.061*
C7	0.3370 (5)	0.6951 (5)	0.5491 (4)	0.0721 (12)
H7	0.3489	0.6158	0.5792	0.087*
C8	0.4683 (7)	0.6885 (10)	0.4361 (5)	0.168 (4)
H8A	0.4600	0.7659	0.4019	0.251*
H8B	0.4671	0.6316	0.3860	0.251*
H8C	0.5617	0.6636	0.4484	0.251*
C9	0.3364 (6)	0.7746 (6)	0.6359 (4)	0.0889 (16)
H9A	0.4234	0.7411	0.6554	0.133*
H9B	0.2455	0.7811	0.7034	0.133*
H9C	0.3398	0.8527	0.6046	0.133*
C10	−0.2363 (5)	0.7879 (5)	0.4785 (4)	0.0864 (15)
H10A	−0.2231	0.8116	0.4013	0.130*
H10B	−0.3119	0.8499	0.5311	0.130*
H10C	−0.2683	0.7151	0.4937	0.130*
S1	0.29307 (13)	0.18189 (11)	0.86238 (11)	0.0636 (4)	0.847 (5)
C16'	0.29307 (13)	0.18189 (11)	0.86238 (11)	0.0636 (4)	0.153 (5)
H16'	0.2049	0.2487	0.8803	0.076*	0.153 (5)
S2	0.13328 (18)	0.84868 (10)	0.98665 (14)	0.0673 (5)	0.700 (5)
C21'	0.13328 (18)	0.84868 (10)	0.98665 (14)	0.0673 (5)	0.300 (5)
H21'	0.1475	0.8704	0.9088	0.081*	0.300 (5)
N1	0.4121 (3)	0.3556 (2)	0.9546 (2)	0.0456 (6)
N2	0.2449 (3)	0.5262 (2)	0.9644 (2)	0.0396 (6)
C11	0.2748 (3)	0.4218 (3)	1.0096 (3)	0.0374 (6)
H11	0.2029	0.3959	1.0769	0.045*
C12	0.3763 (4)	0.5391 (3)	0.8622 (3)	0.0561 (9)
H12A	0.4119	0.6054	0.8711	0.067*
H12B	0.3525	0.5501	0.7948	0.067*
C13	0.4936 (5)	0.4194 (3)	0.8565 (3)	0.0631 (10)
H13A	0.5238	0.3766	0.7860	0.076*
H13B	0.5819	0.4315	0.8633	0.076*
C14	0.4669 (4)	0.2283 (3)	0.9737 (3)	0.0473 (8)
H14A	0.4110	0.2105	1.0515	0.057*
H14B	0.5718	0.2112	0.9631	0.057*
C15	0.4510 (4)	0.1486 (3)	0.8940 (3)	0.0438 (7)
S1'	0.5553 (4)	0.0368 (3)	0.8423 (3)	0.0759 (12)	0.153 (5)
C16	0.5553 (4)	0.0368 (3)	0.8423 (3)	0.0759 (12)	0.847 (5)
H16	0.6534	0.0029	0.8456	0.091*	0.847 (5)
C17	0.4850 (6)	−0.0147 (4)	0.7846 (4)	0.0743 (12)
H17	0.5312	−0.0919	0.7467	0.089*
C18	0.3504 (6)	0.0533 (4)	0.7880 (4)	0.0732 (12)
H18	0.2925	0.0307	0.7515	0.088*
C19	0.1011 (4)	0.6183 (3)	1.0051 (3)	0.0409 (7)
H19A	0.0249	0.5844	1.0610	0.049*
H19B	0.0701	0.6438	0.9419	0.049*
C20	0.1103 (3)	0.7249 (3)	1.0576 (3)	0.0407 (7)
S2'	0.0919 (3)	0.7370 (2)	1.18444 (19)	0.0656 (8)	0.300 (5)
C21	0.0919 (3)	0.7370 (2)	1.18444 (19)	0.0656 (8)	0.700 (5)
H21	0.0762	0.6796	1.2445	0.079*	0.700 (5)
C22	0.1046 (5)	0.8587 (6)	1.1876 (5)	0.0860 (17)
H22	0.0993	0.8925	1.2561	0.103*
C23	0.1235 (5)	0.9205 (3)	1.0935 (5)	0.0765 (14)
H23	0.1310	1.0017	1.0887	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.04018 (15)	0.03358 (14)	0.03059 (14)	−0.01658 (10)	−0.01405 (10)	0.00217 (9)
Cl1	0.0592 (5)	0.0374 (4)	0.0377 (4)	−0.0148 (3)	−0.0163 (3)	−0.0067 (3)
Cl2	0.0554 (5)	0.0370 (4)	0.0484 (4)	−0.0104 (3)	−0.0204 (4)	0.0055 (3)
Cl3	0.0483 (4)	0.0661 (5)	0.0460 (4)	−0.0327 (4)	−0.0158 (3)	0.0045 (4)
C1	0.0502 (19)	0.064 (2)	0.0352 (16)	−0.0304 (17)	−0.0113 (14)	0.0064 (15)
C2	0.0491 (18)	0.057 (2)	0.0325 (15)	−0.0231 (16)	−0.0090 (13)	−0.0027 (14)
C3	0.063 (2)	0.074 (2)	0.0285 (15)	−0.0371 (19)	−0.0185 (15)	0.0043 (15)
C4	0.059 (2)	0.072 (2)	0.0411 (17)	−0.0304 (19)	−0.0257 (16)	0.0210 (17)
C5	0.077 (3)	0.0430 (18)	0.0461 (19)	−0.0207 (17)	−0.0225 (18)	0.0171 (15)
C6	0.072 (2)	0.0484 (19)	0.0451 (18)	−0.0386 (18)	−0.0222 (17)	0.0124 (15)
C7	0.052 (2)	0.115 (4)	0.059 (2)	−0.040 (2)	−0.0186 (18)	−0.004 (2)
C8	0.075 (4)	0.359 (14)	0.081 (4)	−0.099 (6)	−0.003 (3)	−0.044 (6)
C9	0.079 (3)	0.136 (5)	0.076 (3)	−0.051 (3)	−0.040 (3)	−0.002 (3)
C10	0.072 (3)	0.131 (5)	0.073 (3)	−0.032 (3)	−0.046 (2)	0.026 (3)
S1	0.0542 (7)	0.0669 (8)	0.0728 (8)	−0.0065 (5)	−0.0317 (6)	−0.0088 (6)
C16'	0.0542 (7)	0.0669 (8)	0.0728 (8)	−0.0065 (5)	−0.0317 (6)	−0.0088 (6)
S2	0.1003 (11)	0.0355 (6)	0.0966 (11)	−0.0253 (6)	−0.0681 (9)	0.0179 (6)
C21'	0.1003 (11)	0.0355 (6)	0.0966 (11)	−0.0253 (6)	−0.0681 (9)	0.0179 (6)
N1	0.0445 (15)	0.0354 (14)	0.0491 (15)	−0.0070 (12)	−0.0116 (12)	−0.0012 (12)
N2	0.0473 (14)	0.0315 (13)	0.0384 (13)	−0.0116 (11)	−0.0141 (11)	0.0016 (10)
C11	0.0430 (16)	0.0340 (15)	0.0372 (15)	−0.0124 (13)	−0.0158 (13)	0.0010 (12)
C12	0.060 (2)	0.050 (2)	0.0482 (19)	−0.0202 (17)	−0.0080 (17)	0.0082 (16)
C13	0.060 (2)	0.051 (2)	0.059 (2)	−0.0159 (18)	−0.0004 (18)	−0.0002 (18)
C14	0.0436 (17)	0.0380 (17)	0.0561 (19)	0.0002 (14)	−0.0208 (15)	−0.0042 (15)
C15	0.0430 (17)	0.0376 (16)	0.0485 (18)	−0.0077 (13)	−0.0172 (14)	0.0023 (14)
S1'	0.092 (2)	0.0512 (17)	0.090 (2)	−0.0105 (15)	−0.0439 (19)	−0.0045 (15)
C16	0.092 (2)	0.0512 (17)	0.090 (2)	−0.0105 (15)	−0.0439 (19)	−0.0045 (15)
C17	0.097 (3)	0.053 (2)	0.068 (3)	−0.021 (2)	−0.023 (2)	−0.011 (2)
C18	0.095 (3)	0.075 (3)	0.070 (3)	−0.038 (3)	−0.044 (3)	0.005 (2)
C19	0.0448 (17)	0.0319 (15)	0.0511 (18)	−0.0088 (13)	−0.0242 (14)	−0.0002 (13)
C20	0.0374 (15)	0.0326 (15)	0.0533 (18)	−0.0059 (12)	−0.0197 (14)	−0.0032 (13)
S2'	0.0721 (15)	0.0671 (15)	0.0606 (13)	−0.0293 (11)	−0.0207 (11)	0.0003 (10)
C21	0.0721 (15)	0.0671 (15)	0.0606 (13)	−0.0293 (11)	−0.0207 (11)	0.0003 (10)
C22	0.060 (3)	0.115 (4)	0.082 (3)	−0.020 (3)	−0.015 (2)	−0.053 (3)
C23	0.067 (3)	0.0316 (18)	0.133 (5)	−0.0068 (18)	−0.041 (3)	−0.013 (2)

Geometric parameters (Å, º) top

Ru1—C6	2.140 (3)	C10—H10C	0.9599
Ru1—C2	2.154 (3)	S1—C15	1.700 (3)
Ru1—C5	2.173 (3)	S2—C20	1.647 (3)
Ru1—C1	2.180 (3)	N1—C11	1.307 (4)
Ru1—C3	2.191 (3)	N1—C13	1.458 (5)
Ru1—C4	2.207 (3)	N1—C14	1.462 (4)
Ru1—Cl1	2.4157 (11)	N2—C11	1.302 (4)
Ru1—Cl2	2.4329 (11)	N2—C19	1.460 (4)
Ru1—Cl3	2.4417 (11)	N2—C12	1.466 (4)
C1—C6	1.406 (5)	C11—H11	0.9600
C1—C2	1.435 (5)	C12—C13	1.534 (5)
C1—C7	1.521 (5)	C12—H12A	0.9600
C2—C3	1.398 (5)	C12—H12B	0.9600
C2—H2	0.9600	C13—H13A	0.9600
C3—C4	1.419 (6)	C13—H13B	0.9600
C3—H3	0.9600	C14—C15	1.505 (5)
C4—C5	1.422 (5)	C14—H14A	0.9600
C4—C10	1.495 (5)	C14—H14B	0.9600
C5—C6	1.421 (5)	C15—S1'	1.438 (4)
C5—H5	0.9600	S1'—H16	0.960 (3)
C6—H6	0.9600	C17—C18	1.338 (7)
C7—C9	1.492 (6)	C17—H17	0.9600
C7—C8	1.502 (7)	C18—H18	0.9600
C7—H7	0.9600	C19—C20	1.495 (4)
C8—H8A	0.9599	C19—H19A	0.9600
C8—H8B	0.9599	C19—H19B	0.9600
C8—H8C	0.9599	C20—S2'	1.558 (4)
C9—H9A	0.9599	S2'—H21	0.960 (2)
C9—H9B	0.9599	C22—C23	1.310 (7)
C9—H9C	0.9599	C22—H22	0.9600
C10—H10A	0.9599	C23—H23	0.9600
C10—H10B	0.9599

C6—Ru1—C2	68.59 (14)	Ru1—C6—H6	128.9
C6—Ru1—C5	38.46 (15)	C9—C7—C8	113.3 (5)
C2—Ru1—C5	80.93 (15)	C9—C7—C1	113.7 (4)
C6—Ru1—C1	37.98 (14)	C8—C7—C1	109.7 (4)
C2—Ru1—C1	38.66 (13)	C9—C7—H7	106.5
C5—Ru1—C1	69.25 (15)	C8—C7—H7	106.5
C6—Ru1—C3	81.08 (14)	C1—C7—H7	106.5
C2—Ru1—C3	37.52 (13)	C7—C8—H8A	109.5
C5—Ru1—C3	68.20 (15)	C7—C8—H8B	109.5
C1—Ru1—C3	69.15 (13)	H8A—C8—H8B	109.5
C6—Ru1—C4	68.92 (14)	C7—C8—H8C	109.5
C2—Ru1—C4	68.06 (14)	H8A—C8—H8C	109.5
C5—Ru1—C4	37.88 (15)	H8B—C8—H8C	109.5
C1—Ru1—C4	81.91 (13)	C7—C9—H9A	109.5
C3—Ru1—C4	37.65 (15)	C7—C9—H9B	109.5
C6—Ru1—Cl1	86.77 (10)	H9A—C9—H9B	109.5
C2—Ru1—Cl1	144.83 (9)	C7—C9—H9C	109.5
C5—Ru1—Cl1	95.39 (11)	H9A—C9—H9C	109.5
C1—Ru1—Cl1	107.28 (10)	H9B—C9—H9C	109.5
C3—Ru1—Cl1	163.52 (11)	C4—C10—H10A	109.5
C4—Ru1—Cl1	126.94 (11)	C4—C10—H10B	109.5
C6—Ru1—Cl2	124.11 (11)	H10A—C10—H10B	109.5
C2—Ru1—Cl2	87.76 (11)	C4—C10—H10C	109.5
C5—Ru1—Cl2	162.10 (11)	H10A—C10—H10C	109.5
C1—Ru1—Cl2	93.29 (10)	H10B—C10—H10C	109.5
C3—Ru1—Cl2	110.15 (11)	C11—N1—C13	110.3 (3)
C4—Ru1—Cl2	146.86 (11)	C11—N1—C14	125.0 (3)
Cl1—Ru1—Cl2	85.88 (4)	C13—N1—C14	123.6 (3)
C6—Ru1—Cl3	147.20 (11)	C11—N2—C19	126.2 (3)
C2—Ru1—Cl3	126.23 (9)	C11—N2—C12	110.5 (3)
C5—Ru1—Cl3	110.17 (12)	C19—N2—C12	123.3 (3)
C1—Ru1—Cl3	164.68 (9)	N2—C11—N1	113.6 (3)
C3—Ru1—Cl3	96.15 (10)	N2—C11—H11	123.2
C4—Ru1—Cl3	88.90 (10)	N1—C11—H11	123.2
Cl1—Ru1—Cl3	88.04 (4)	N2—C12—C13	102.5 (3)
Cl2—Ru1—Cl3	87.71 (4)	N2—C12—H12A	111.3
C6—C1—C2	116.7 (3)	C13—C12—H12A	111.3
C6—C1—C7	124.6 (4)	N2—C12—H12B	111.3
C2—C1—C7	118.6 (4)	C13—C12—H12B	111.3
C6—C1—Ru1	69.44 (19)	H12A—C12—H12B	109.2
C2—C1—Ru1	69.67 (19)	N1—C13—C12	103.2 (3)
C7—C1—Ru1	128.6 (3)	N1—C13—H13A	111.1
C3—C2—C1	122.3 (3)	C12—C13—H13A	111.1
C3—C2—Ru1	72.69 (19)	N1—C13—H13B	111.1
C1—C2—Ru1	71.67 (19)	C12—C13—H13B	111.1
C3—C2—H2	118.9	H13A—C13—H13B	109.1
C1—C2—H2	118.9	N1—C14—C15	112.6 (3)
Ru1—C2—H2	129.3	N1—C14—H14A	109.1
C2—C3—C4	120.1 (3)	C15—C14—H14A	109.1
C2—C3—Ru1	69.79 (18)	N1—C14—H14B	109.1
C4—C3—Ru1	71.78 (19)	C15—C14—H14B	109.1
C2—C3—H3	119.9	H14A—C14—H14B	107.8
C4—C3—H3	119.9	S1'—C15—C14	126.7 (3)
Ru1—C3—H3	131.2	S1'—C15—S1	112.4 (3)
C3—C4—C5	118.9 (3)	C14—C15—S1	120.8 (2)
C3—C4—C10	120.4 (4)	C15—S1'—H16	126.4 (3)
C5—C4—C10	120.7 (4)	C18—C17—H17	122.6
C3—C4—Ru1	70.57 (19)	C17—C18—H18	123.4
C5—C4—Ru1	69.77 (19)	N2—C19—C20	112.8 (3)
C10—C4—Ru1	129.5 (3)	N2—C19—H19A	109.0
C6—C5—C4	119.9 (4)	C20—C19—H19A	109.0
C6—C5—Ru1	69.50 (19)	N2—C19—H19B	109.0
C4—C5—Ru1	72.4 (2)	C20—C19—H19B	109.0
C6—C5—H5	120.1	H19A—C19—H19B	107.8
C4—C5—H5	120.1	C19—C20—S2'	125.7 (3)
Ru1—C5—H5	130.7	C19—C20—S2	122.6 (3)
C1—C6—C5	122.1 (3)	S2'—C20—S2	111.7 (2)
C1—C6—Ru1	72.58 (19)	C20—S2'—H21	129.3 (2)
C5—C6—Ru1	72.0 (2)	C23—C22—H22	121.2
C1—C6—H6	119.0	C22—C23—H23	122.8
C5—C6—H6	119.0

C2—Ru1—C1—C6	130.7 (3)	Cl2—Ru1—C4—C5	−150.0 (2)
C5—Ru1—C1—C6	28.9 (2)	Cl3—Ru1—C4—C5	125.9 (2)
C3—Ru1—C1—C6	102.6 (2)	C6—Ru1—C4—C10	−143.0 (5)
C4—Ru1—C1—C6	65.9 (2)	C2—Ru1—C4—C10	142.5 (5)
Cl1—Ru1—C1—C6	−60.4 (2)	C5—Ru1—C4—C10	−113.6 (5)
Cl2—Ru1—C1—C6	−147.07 (19)	C1—Ru1—C4—C10	180.0 (5)
Cl3—Ru1—C1—C6	119.6 (4)	C3—Ru1—C4—C10	113.8 (5)
C6—Ru1—C1—C2	−130.7 (3)	Cl1—Ru1—C4—C10	−74.4 (5)
C5—Ru1—C1—C2	−101.8 (2)	Cl2—Ru1—C4—C10	96.4 (4)
C3—Ru1—C1—C2	−28.1 (2)	Cl3—Ru1—C4—C10	12.3 (4)
C4—Ru1—C1—C2	−64.8 (2)	C3—C4—C5—C6	0.2 (5)
Cl1—Ru1—C1—C2	168.98 (18)	C10—C4—C5—C6	177.4 (3)
Cl2—Ru1—C1—C2	82.3 (2)	Ru1—C4—C5—C6	52.7 (3)
Cl3—Ru1—C1—C2	−11.0 (5)	C3—C4—C5—Ru1	−52.5 (3)
C6—Ru1—C1—C7	118.5 (4)	C10—C4—C5—Ru1	124.7 (3)
C2—Ru1—C1—C7	−110.9 (4)	C2—Ru1—C5—C6	−66.8 (2)
C5—Ru1—C1—C7	147.4 (4)	C1—Ru1—C5—C6	−28.6 (2)
C3—Ru1—C1—C7	−138.9 (4)	C3—Ru1—C5—C6	−103.6 (2)
C4—Ru1—C1—C7	−175.6 (4)	C4—Ru1—C5—C6	−132.6 (3)
Cl1—Ru1—C1—C7	58.1 (4)	Cl1—Ru1—C5—C6	77.9 (2)
Cl2—Ru1—C1—C7	−28.6 (4)	Cl2—Ru1—C5—C6	−15.4 (5)
Cl3—Ru1—C1—C7	−121.9 (4)	Cl3—Ru1—C5—C6	167.78 (19)
C6—C1—C2—C3	1.9 (5)	C6—Ru1—C5—C4	132.6 (3)
C7—C1—C2—C3	178.4 (3)	C2—Ru1—C5—C4	65.7 (2)
Ru1—C1—C2—C3	54.6 (3)	C1—Ru1—C5—C4	104.0 (2)
C6—C1—C2—Ru1	−52.7 (3)	C3—Ru1—C5—C4	29.0 (2)
C7—C1—C2—Ru1	123.8 (3)	Cl1—Ru1—C5—C4	−149.5 (2)
C6—Ru1—C2—C3	−103.7 (2)	Cl2—Ru1—C5—C4	117.2 (3)
C5—Ru1—C2—C3	−65.8 (2)	Cl3—Ru1—C5—C4	−59.6 (2)
C1—Ru1—C2—C3	−133.8 (3)	C2—C1—C6—C5	−1.9 (5)
C4—Ru1—C2—C3	−28.7 (2)	C7—C1—C6—C5	−178.1 (3)
Cl1—Ru1—C2—C3	−152.29 (18)	Ru1—C1—C6—C5	−54.7 (3)
Cl2—Ru1—C2—C3	128.1 (2)	C2—C1—C6—Ru1	52.8 (3)
Cl3—Ru1—C2—C3	42.6 (3)	C7—C1—C6—Ru1	−123.4 (3)
C6—Ru1—C2—C1	30.1 (2)	C4—C5—C6—C1	0.9 (5)
C5—Ru1—C2—C1	68.0 (2)	Ru1—C5—C6—C1	54.9 (3)
C3—Ru1—C2—C1	133.8 (3)	C4—C5—C6—Ru1	−54.0 (3)
C4—Ru1—C2—C1	105.1 (2)	C2—Ru1—C6—C1	−30.6 (2)
Cl1—Ru1—C2—C1	−18.5 (3)	C5—Ru1—C6—C1	−133.4 (3)
Cl2—Ru1—C2—C1	−98.1 (2)	C3—Ru1—C6—C1	−67.4 (2)
Cl3—Ru1—C2—C1	176.40 (17)	C4—Ru1—C6—C1	−104.4 (2)
C1—C2—C3—C4	−0.9 (5)	Cl1—Ru1—C6—C1	123.77 (19)
Ru1—C2—C3—C4	53.2 (3)	Cl2—Ru1—C6—C1	41.0 (2)
C1—C2—C3—Ru1	−54.1 (3)	Cl3—Ru1—C6—C1	−154.91 (17)
C6—Ru1—C3—C2	66.3 (2)	C2—Ru1—C6—C5	102.8 (2)
C5—Ru1—C3—C2	104.0 (2)	C1—Ru1—C6—C5	133.4 (3)
C1—Ru1—C3—C2	28.8 (2)	C3—Ru1—C6—C5	66.0 (2)
C4—Ru1—C3—C2	133.2 (3)	C4—Ru1—C6—C5	29.0 (2)
Cl1—Ru1—C3—C2	109.2 (4)	Cl1—Ru1—C6—C5	−102.8 (2)
Cl2—Ru1—C3—C2	−56.9 (2)	Cl2—Ru1—C6—C5	174.34 (18)
Cl3—Ru1—C3—C2	−146.7 (2)	Cl3—Ru1—C6—C5	−21.5 (3)
C6—Ru1—C3—C4	−66.9 (2)	C6—C1—C7—C9	15.6 (6)
C2—Ru1—C3—C4	−133.2 (3)	C2—C1—C7—C9	−160.6 (4)
C5—Ru1—C3—C4	−29.1 (2)	Ru1—C1—C7—C9	−74.7 (5)
C1—Ru1—C3—C4	−104.3 (2)	C6—C1—C7—C8	−112.5 (6)
Cl1—Ru1—C3—C4	−23.9 (5)	C2—C1—C7—C8	71.4 (6)
Cl2—Ru1—C3—C4	169.95 (18)	Ru1—C1—C7—C8	157.2 (5)
Cl3—Ru1—C3—C4	80.1 (2)	C19—N2—C11—N1	178.8 (3)
C2—C3—C4—C5	−0.2 (5)	C12—N2—C11—N1	0.4 (4)
Ru1—C3—C4—C5	52.1 (3)	C13—N1—C11—N2	0.0 (4)
C2—C3—C4—C10	−177.4 (3)	C14—N1—C11—N2	−168.6 (3)
Ru1—C3—C4—C10	−125.1 (3)	C11—N2—C12—C13	−0.6 (4)
C2—C3—C4—Ru1	−52.3 (3)	C19—N2—C12—C13	−179.1 (3)
C6—Ru1—C4—C3	103.2 (2)	C11—N1—C13—C12	−0.4 (4)
C2—Ru1—C4—C3	28.6 (2)	C14—N1—C13—C12	168.4 (3)
C5—Ru1—C4—C3	132.6 (3)	N2—C12—C13—N1	0.6 (4)
C1—Ru1—C4—C3	66.1 (2)	C11—N1—C14—C15	93.3 (4)
Cl1—Ru1—C4—C3	171.72 (16)	C13—N1—C14—C15	−73.9 (4)
Cl2—Ru1—C4—C3	−17.4 (3)	N1—C14—C15—S1'	143.0 (3)
Cl3—Ru1—C4—C3	−101.6 (2)	N1—C14—C15—S1	−40.9 (4)
C6—Ru1—C4—C5	−29.4 (2)	C11—N2—C19—C20	109.6 (4)
C2—Ru1—C4—C5	−103.9 (2)	C12—N2—C19—C20	−72.2 (4)
C1—Ru1—C4—C5	−66.4 (2)	N2—C19—C20—S2'	−84.8 (4)
C3—Ru1—C4—C5	−132.6 (3)	N2—C19—C20—S2	98.6 (3)
Cl1—Ru1—C4—C5	39.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1ⁱ	0.96	2.62	3.450 (4)	144
C14—H14A···Cl1ⁱ	0.96	2.82	3.553 (4)	134
C19—H19A···Cl2ⁱ	0.96	2.81	3.671 (4)	150
C23—H23···Cl1ⁱⁱ	0.96	2.66	3.549 (4)	154
C14—H14B···Cg2ⁱⁱⁱ	0.96	2.83	3.784 (5)	171
C19—H19B···Cl1	0.96	2.86	3.759 (5)	157

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	(C₁₃H₁₅N₂S₂)[RuCl₃(C₁₀H₁₄)]
M_r	605.02
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	9.910 (2), 11.600 (2), 12.659 (3)
α, β, γ (°)	84.95 (3), 67.05 (3), 74.14 (3)
V (Å³)	1288.8 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.10
Crystal size (mm)	0.48 × 0.19 × 0.17

Data collection
Diffractometer	Rigaku AFC-8S Mercury CCD diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.621, 0.836
No. of measured, independent and observed [I > 2σ(I)] reflections	11095, 4557, 4062
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.084, 1.13
No. of reflections	4557
No. of parameters	285
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.68

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1ⁱ	0.96	2.62	3.450 (4)	144
C14—H14A···Cl1ⁱ	0.96	2.82	3.553 (4)	134
C19—H19A···Cl2ⁱ	0.96	2.81	3.671 (4)	150
C23—H23···Cl1ⁱⁱ	0.96	2.66	3.549 (4)	154
C14—H14B···Cg2ⁱⁱⁱ	0.96	2.83	3.784 (5)	171
C19—H19B···Cl1	0.96	2.86	3.759 (5)	157

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+1, −z+2.

Acknowledgements

We thank the Technological and Scientific Research Council of Turkey TÜBİTAK-CNRS [TBAG-U/181 (106 T716)] and İnönü University Research Fund (BAP: 2008-Güdümlü3) for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Arduengo, A. J. & Krafczyc, R. (1998). Chem. Ztg, 32, 6–14. CAS Google Scholar
Arslan, H., VanDerveer, D., Özdemir, İ., Çetinkaya, B. & Demir, S. (2005a). J. Chem. Crystallogr. 35, 491–495. Web of Science CSD CrossRef CAS Google Scholar
Arslan, H., VanDerveer, D., Özdemir, I., Yaşar, S. & Çetinkaya, B. (2005b). Acta Cryst. E61, m1873–m1875. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arslan, H., VanDerveer, D., Yaşar, S., Özdemir, İ. & Çetinkaya, B. (2007). Acta Cryst. E63, m1001–m1003. Web of Science CSD CrossRef IUCr Journals Google Scholar
Crundwell, G., Meskill, T., Sayers, D. & Kantardjieff, K. (2002). Acta Cryst. E58, o668–o670. Web of Science CSD CrossRef IUCr Journals Google Scholar
Herrmann, W. A. (2002). Angew. Chem. Int. Ed. 41, 1290–1309. Web of Science CrossRef CAS Google Scholar
Herrmann, W. A., Elison, M., Fischer, J., Köcher, C. & Artus, G. R. J. (1995). Angew. Chem. Int. Ed. Engl. 34, 2371–2374. CrossRef CAS Web of Science Google Scholar
Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA. Google Scholar
Linehan, J., Crundwell, G., Herron, S. R. & Kantardjieff, K. A. (2003). Acta Cryst. E59, o466–o468. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, L., Zhang, Q.-F. & Leung, W.-H. (2004). Acta Cryst. E60, m506–m508. Web of Science CSD CrossRef IUCr Journals Google Scholar
Navarro, O., Marion, N., Oonishi, Y., Kelly, R. A. & Nolan, S. P. (2006). J. Org. Chem. 71, 685–692. Web of Science CrossRef PubMed CAS Google Scholar
Özdemir, İ., Demir, S., Çetinkaya, B. & Çetinkaya, E. (2005). J. Organomet. Chem. 690, 5849–5855. Google Scholar
Özdemir, İ., Demir, S., Çetinkaya, B., Toupet, L., Castarlanes, R., Fischmeister, C. & Dixneuf, P. H. (2007). Eur. J. Inorg. Chem. 18, 2862–2869. Google Scholar
Özdemir, İ., Gürbüz, N., Gök, Y. & Çetinkaya, B. (2008). Heteroat. Chem. 19, 82–86. Google Scholar
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sonar, V. N., Parkin, S. & Crooks, P. A. (2004). Acta Cryst. C60, o217–o218. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sonar, V. N., Parkin, S. & Crooks, P. A. (2005a). Acta Cryst. E61, o933–o935. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sonar, V. N., Parkin, S. & Crooks, P. A. (2005b). Acta Cryst. C61, o78–o80. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Therrien, B., Frein, S. & Süss-Fink, G. (2004). Acta Cryst. E60, m1666–m1668. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wagner, P., Officer, D. L. & Kubicki, M. (2006a). Acta Cryst. E62, o5745–o5747. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wagner, P., Officer, D. L. & Kubicki, M. (2006b). Acta Cryst. E62, o5931–o5932. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yaşar, S., Özdemir, İ., Çetinkaya, B., Renaud, J. L. & Bruneau, C. (2008). Eur. J. Org. Chem. 12, 2142–2149. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.