cis-Bis(2,2′-bipyridine-κ2N,N′)carbonyl­chloridoruthenium(II) hexa­fluorido­phosphate

Takase, T.; Mun, B.; Oyama, D.

doi:10.1107/S1600536812048246

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 1| January 2013| Pages m1-m2

https://doi.org/10.1107/S1600536812048246

Open

access

cis-Bis(2,2′-bipyridine-κ²N,N′)carbonylchloridoruthenium(II) hexafluoridophosphate

Tsugiko Takase,^a Bisa Mun ^b and Dai Oyama ^c ^*

^aCenter for Practical and Project-Based Learning, Cluster of Science and Technology, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan, ^bDepartment of Materials Science, Graduate School of Science and Technology, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan, and ^cDepartment of Industrial Systems Engineering, Cluster of Science and Technology, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan
^*Correspondence e-mail: daio@sss.fukushima-u.ac.jp

(Received 15 November 2012; accepted 24 November 2012; online 5 December 2012)

In the title compound, [RuCl(C₁₀H₈N₂)₂(CO)]PF₆, the Ru^II atom is coordinated in a distorted octahedral geometry by four N atoms of the bipyridine ligands, a carbonyl C atom and a chloride ion. The carbonyl and chloride ligands in the cation adopt a mutually cis arrangement and these are disordered over two sets of sites with site occupancies of 0.721 (6) and 0.279 (6). The Ru—N bond length [2.117 (2) Å] trans to the carbonyl ligand is slightly longer than the average of the other Ru—N bond lengths (2.08 Å), which can be explained by the expected trans influence of the carbonyl group. In the crystal, weak C—H⋯F interactions are observed between the complex cation and the PF₆⁻ anion, leading to the formation of a three-dimensional supramolecular structure. The crystal studied was an inversion twin with twin fractions of 0.78 (4) and 0.22 (4).

Related literature

For details of the synthesis, see: Oyama et al. (2012 ). For a related structure, see: Clear et al. (1980 ). For general background to catalytic reactions using [Ru(bpy)₂(CO)Cl]⁺, see: Ishida et al. (1986 ); Lehn & Ziessel (1990 ).

Experimental

Crystal data

[RuCl(C₁₀H₈N₂)₂(CO)]·PF₆
M_r = 621.87
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.882 (5) Å
b = 12.063 (5) Å
c = 17.410 (7) Å
V = 2285.2 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 93 K
0.20 × 0.10 × 0.02 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.897, T_max = 0.981
22875 measured reflections
5177 independent reflections
4689 reflections with F² > 2σ(F²)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.062
S = 1.08
5177 reflections
330 parameters
H-atom parameters constrained
Δρ_max = 1.37 e Å⁻³
Δρ_min = −1.28 e Å⁻³
Absolute structure: Flack (1983 ), 2249 Friedel pairs
Flack parameter: 0.22 (4)

Table 1
Selected bond lengths (Å)

Ru1—Cl1	2.3521 (17)
Ru1—N1	2.086 (2)
Ru1—N2	2.070 (2)
Ru1—N3	2.070 (2)
Ru1—N4	2.117 (2)
Ru1—C21	1.890 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯F2ⁱ	0.95	2.46	3.166 (4)	131
C4—H4⋯F1ⁱⁱ	0.95	2.41	3.257 (4)	148
C7—H5⋯F1ⁱⁱ	0.95	2.54	3.431 (4)	156
C8—H6⋯F2ⁱⁱⁱ	0.95	2.50	3.265 (4)	138
C13—H11⋯F5^iv	0.95	2.39	3.331 (4)	168
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear-SM (Rigaku, 2009 ); cell refinement: CrystalClear-SM; data reduction: CrystalClear-SM; 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, 2012 ); software used to prepare material for publication: CrystalStructure (Rigaku, 2006 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812048246/is5220sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812048246/is5220Isup2.hkl

checkCIF report

Comment top

Ruthenium(II) complexes containing both carbonyl and polypyridyl-based supporting ligands have been studied as catalysts for the reduction of carbon dioxide and in the water-gas shift reaction (Ishida et al., 1986; Lehn & Ziessel, 1990). Of the series complexes, [Ru(bpy)₂(CO)Cl]⁺ (bpy = 2,2'-bipyridine) has been used not only as catalysts but also as a precursor to a family of [Ru(bpy)₂(CO)L]ⁿ⁺-type complexes (L = monodentate ligand). We have used the complex as the starting point for the preparation of more complex functional systems, and we report here the crystal structure of its hexafluoridophosphate salt.

The Ru^II atom has a distorted octahedral geometry, with four N atoms of the bidentate bipyridine ligands, a carbonyl carbon, and a chloride ion completing the first coordination sphere. The CO and Cl ligands in the cation are mutually cis arrangement (Fig. 1) and these are disordered over two sets of sites with site occupancies of 0.721 (6) and 0.279 (6). The Ru—N length trans to the CO ligand [2.117 (2) Å] is slightly longer than the average of other Ru—N lengths (2.08 Å) (Table 1). This can be explained by the expected trans influence of the CO group. In the crystal, the complex cation and the PF₆^- anion are linked via a number of weak C—H···F interactions, leading to the formation of a three-dimensional supramolecular structure. The crystal studied was an inversion twin with twin fractions of 0.78 (4) and 0.22 (4). The bond parameters of the complex are closely comparable to those of the reported ClO₄^- salt, although the corresponding ClO₄^- salt was refined using anisotropic temperature factors for Ru and Cl only (Clear et al., 1980).

Related literature top

For details of the synthesis, see: Oyama et al. (2012). For a related structure, see: Clear et al. (1980). For general background to catalytic reactions using [Ru(bpy)₂(CO)Cl]⁺, see: Ishida et al. (1986); Lehn & Ziessel (1990).

Experimental top

The title compound was prepared according to a literature procedure (Oyama et al., 2012). X-ray quality crystals were grown by the diffusion of diethyl ether into an acetone solution of the complex over a week.

Structure description top

For details of the synthesis, see: Oyama et al. (2012). For a related structure, see: Clear et al. (1980). For general background to catalytic reactions using [Ru(bpy)₂(CO)Cl]⁺, see: Ishida et al. (1986); Lehn & Ziessel (1990).

Computing details top

Data collection: CrystalClear-SM (Rigaku, 2009); cell refinement: CrystalClear-SM (Rigaku, 2009); data reduction: CrystalClear-SM (Rigaku, 2009); 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, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2006).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. Only major component of the disordered CO and Cl ligands is shown.

cis-Bis(2,2'-bipyridine- κ²N,N')carbonylchloridoruthenium(II) hexafluoridophosphate top

Crystal data top

[RuCl(C₁₀H₈N₂)₂(CO)]·PF₆	F(000) = 1232.00
M_r = 621.87	D_x = 1.807 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6659 reflections
a = 10.882 (5) Å	θ = 3.4–27.4°
b = 12.063 (5) Å	µ = 0.95 mm⁻¹
c = 17.410 (7) Å	T = 93 K
V = 2285.2 (17) Å³	Block, orange
Z = 4	0.20 × 0.10 × 0.02 mm

Data collection top

Rigaku Saturn diffractometer	4689 reflections with F² > 2σ(F²)
Detector resolution: 7.31 pixels mm^-1	R_int = 0.045
ω scans	θ_max = 27.4°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −14→14
T_min = 0.897, T_max = 0.981	k = −15→15
22875 measured reflections	l = −22→22
5177 independent reflections

Refinement top

Refinement on F²	w = 1/[σ²(F_o²) + (0.0116P)² + 2.2808P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.032	(Δ/σ)_max = 0.001
wR(F²) = 0.062	Δρ_max = 1.37 e Å⁻³
S = 1.08	Δρ_min = −1.28 e Å⁻³
5177 reflections	Absolute structure: Flack (1983), 2249 Friedel pairs
330 parameters	Absolute structure parameter: 0.22 (4)
H-atom parameters constrained

Crystal data top

[RuCl(C₁₀H₈N₂)₂(CO)]·PF₆	V = 2285.2 (17) Å³
M_r = 621.87	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.882 (5) Å	µ = 0.95 mm⁻¹
b = 12.063 (5) Å	T = 93 K
c = 17.410 (7) Å	0.20 × 0.10 × 0.02 mm

Data collection top

Rigaku Saturn diffractometer	5177 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	4689 reflections with F² > 2σ(F²)
T_min = 0.897, T_max = 0.981	R_int = 0.045
22875 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.062	Δρ_max = 1.37 e Å⁻³
S = 1.08	Δρ_min = −1.28 e Å⁻³
5177 reflections	Absolute structure: Flack (1983), 2249 Friedel pairs
330 parameters	Absolute structure parameter: 0.22 (4)

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ru1	0.02797 (3)	0.23729 (2)	0.135509 (15)	0.01786 (6)
Cl1	−0.09514 (14)	0.07702 (15)	0.13630 (11)	0.0212 (5)	0.721 (6)
Cl2	0.1924 (6)	0.1234 (4)	0.1216 (3)	0.0179 (16)*	0.279 (6)
P1	0.43909 (9)	0.30250 (7)	0.35040 (5)	0.0207 (2)
F1	0.3130 (2)	0.35010 (18)	0.38378 (14)	0.0404 (6)
F2	0.56516 (17)	0.25391 (18)	0.31614 (11)	0.0265 (4)
F3	0.4530 (2)	0.41078 (15)	0.29742 (11)	0.0267 (4)
F4	0.5138 (2)	0.36277 (16)	0.41762 (12)	0.0366 (6)
F5	0.4261 (2)	0.19318 (16)	0.40319 (12)	0.0366 (6)
F6	0.36435 (17)	0.24099 (19)	0.28323 (11)	0.0254 (4)
O1	0.2506 (4)	0.0882 (3)	0.1258 (2)	0.0295 (10)	0.721 (6)
O2	−0.1251 (10)	0.0222 (11)	0.1282 (6)	0.027 (2)*	0.279 (6)
N1	0.1347 (2)	0.3805 (2)	0.12773 (18)	0.0172 (6)
N2	0.0354 (2)	0.2586 (2)	0.01763 (13)	0.0158 (5)
N3	0.0041 (2)	0.2422 (2)	0.25340 (14)	0.0159 (5)
N4	−0.1287 (2)	0.3405 (2)	0.14489 (17)	0.0168 (6)
C1	0.1837 (3)	0.4363 (3)	0.1868 (2)	0.0207 (7)
C2	0.2568 (3)	0.5285 (3)	0.1763 (2)	0.0226 (8)
C3	0.2804 (3)	0.5650 (2)	0.1025 (2)	0.0230 (8)
C4	0.2297 (3)	0.5082 (2)	0.0408 (2)	0.0200 (7)
C5	0.1558 (3)	0.4162 (2)	0.05464 (19)	0.0153 (7)
C6	0.0964 (3)	0.3508 (2)	−0.00646 (19)	0.0163 (7)
C7	0.0989 (3)	0.3809 (2)	−0.0836 (2)	0.0183 (7)
C8	0.0351 (3)	0.3163 (2)	−0.1360 (2)	0.0220 (6)
C9	−0.0250 (3)	0.2223 (2)	−0.11146 (18)	0.0203 (6)
C10	−0.0236 (3)	0.1960 (2)	−0.03456 (19)	0.0203 (7)
C11	0.0752 (3)	0.1916 (2)	0.3056 (2)	0.0255 (8)
C12	0.0524 (3)	0.1979 (2)	0.3838 (2)	0.0251 (8)
C13	−0.0466 (3)	0.2590 (3)	0.40917 (18)	0.0266 (7)
C14	−0.1208 (3)	0.3123 (2)	0.3563 (2)	0.0240 (7)
C15	−0.0943 (3)	0.3029 (2)	0.27831 (19)	0.0159 (7)
C16	−0.1674 (3)	0.3575 (2)	0.2178 (2)	0.0159 (7)
C17	−0.2693 (3)	0.4242 (2)	0.2327 (2)	0.0186 (7)
C18	−0.3292 (3)	0.4755 (2)	0.1729 (2)	0.0215 (8)
C19	−0.2875 (3)	0.4598 (3)	0.0984 (2)	0.0238 (8)
C20	−0.1878 (3)	0.3906 (3)	0.0875 (2)	0.0218 (8)
C21	0.1713 (8)	0.1488 (6)	0.1328 (5)	0.0264 (19)	0.721 (6)
C22	−0.080 (2)	0.1111 (17)	0.1316 (15)	0.033 (6)*	0.279 (6)
H1	0.1674	0.4116	0.2376	0.025*
H2	0.2905	0.5664	0.2193	0.027*
H3	0.3307	0.6282	0.0940	0.028*
H4	0.2453	0.5319	−0.0103	0.024*
H5	0.1434	0.4444	−0.1000	0.022*
H6	0.0328	0.3368	−0.1887	0.026*
H7	−0.0668	0.1761	−0.1471	0.024*
H8	−0.0658	0.1315	−0.0178	0.024*
H9	0.1439	0.1499	0.2884	0.031*
H10	0.1042	0.1606	0.4193	0.030*
H11	−0.0637	0.2646	0.4626	0.032*
H12	−0.1893	0.3548	0.3730	0.029*
H13	−0.2971	0.4342	0.2840	0.022*
H14	−0.3986	0.5212	0.1826	0.026*
H15	−0.3262	0.4956	0.0562	0.029*
H16	−0.1601	0.3781	0.0365	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.02530 (13)	0.01498 (11)	0.01331 (11)	0.00333 (12)	0.00509 (12)	0.00234 (11)
Cl1	0.0230 (7)	0.0190 (11)	0.0215 (7)	−0.0062 (6)	−0.0010 (6)	0.0016 (7)
P1	0.0266 (5)	0.0181 (4)	0.0175 (5)	−0.0013 (3)	0.0036 (3)	−0.0010 (3)
F1	0.0323 (13)	0.0377 (13)	0.0512 (18)	−0.0069 (10)	0.0251 (11)	−0.0185 (11)
F2	0.0229 (10)	0.0255 (10)	0.0311 (10)	0.0082 (10)	−0.0030 (8)	0.0033 (10)
F3	0.0298 (13)	0.0196 (9)	0.0306 (12)	0.0037 (9)	0.0006 (9)	0.0086 (8)
F4	0.0600 (17)	0.0284 (10)	0.0215 (11)	−0.0152 (11)	−0.0104 (11)	−0.0022 (8)
F5	0.0713 (19)	0.0218 (10)	0.0167 (11)	−0.0173 (11)	0.0028 (11)	0.0042 (8)
F6	0.0251 (10)	0.0268 (11)	0.0244 (10)	−0.0022 (10)	−0.0034 (8)	−0.0066 (9)
O1	0.024 (2)	0.026 (2)	0.039 (2)	0.0095 (19)	−0.0004 (19)	0.0067 (18)
N1	0.0216 (15)	0.0180 (13)	0.0121 (15)	0.0040 (11)	0.0011 (13)	−0.0017 (12)
N2	0.0201 (14)	0.0134 (12)	0.0140 (12)	−0.0018 (14)	0.0044 (11)	−0.0008 (10)
N3	0.0141 (14)	0.0190 (13)	0.0147 (12)	−0.0027 (11)	0.0012 (9)	0.0025 (11)
N4	0.0239 (15)	0.0151 (13)	0.0116 (15)	0.0003 (11)	−0.0002 (13)	−0.0018 (11)
C1	0.0169 (19)	0.0297 (19)	0.0153 (18)	0.0050 (15)	−0.0023 (14)	−0.0040 (15)
C2	0.026 (2)	0.020 (2)	0.022 (2)	0.0020 (16)	−0.0089 (16)	−0.0070 (15)
C3	0.024 (2)	0.0150 (17)	0.030 (2)	−0.0003 (15)	−0.0088 (16)	−0.0019 (15)
C4	0.028 (2)	0.0141 (17)	0.0185 (18)	−0.0008 (15)	−0.0035 (15)	0.0021 (13)
C5	0.0173 (18)	0.0134 (16)	0.0152 (17)	0.0017 (13)	−0.0033 (14)	−0.0012 (13)
C6	0.0152 (17)	0.0149 (16)	0.0188 (18)	0.0034 (13)	0.0006 (13)	−0.0007 (13)
C7	0.0173 (18)	0.0190 (17)	0.0186 (18)	−0.0043 (14)	−0.0007 (14)	0.0027 (13)
C8	0.0235 (17)	0.0278 (15)	0.0146 (16)	−0.0045 (15)	−0.0016 (19)	−0.0008 (14)
C9	0.0211 (16)	0.0213 (15)	0.0186 (16)	−0.0009 (17)	−0.0008 (14)	−0.0059 (12)
C10	0.0223 (17)	0.0141 (14)	0.0243 (18)	−0.0012 (16)	0.0053 (16)	−0.0044 (12)
C11	0.026 (2)	0.0279 (19)	0.0225 (19)	0.0012 (16)	−0.0009 (16)	0.0075 (15)
C12	0.026 (2)	0.0299 (18)	0.0191 (19)	−0.0031 (15)	−0.0068 (14)	0.0050 (13)
C13	0.038 (2)	0.0280 (18)	0.0140 (14)	−0.0004 (19)	−0.0012 (14)	0.0008 (15)
C14	0.032 (2)	0.0218 (16)	0.0178 (18)	0.0012 (14)	0.0023 (17)	−0.0022 (15)
C15	0.0179 (17)	0.0160 (15)	0.0140 (16)	−0.0010 (13)	0.0012 (13)	0.0013 (12)
C16	0.0179 (18)	0.0130 (16)	0.0167 (17)	−0.0040 (13)	−0.0010 (13)	−0.0008 (12)
C17	0.0165 (17)	0.0177 (17)	0.0216 (19)	−0.0022 (13)	0.0038 (14)	−0.0015 (14)
C18	0.0165 (19)	0.0169 (17)	0.031 (2)	0.0016 (15)	0.0014 (16)	0.0010 (15)
C19	0.021 (2)	0.0210 (18)	0.029 (2)	0.0009 (15)	−0.0025 (17)	0.0074 (16)
C20	0.023 (2)	0.0237 (19)	0.0193 (19)	0.0031 (15)	−0.0012 (15)	0.0017 (15)
C21	0.042 (5)	0.015 (3)	0.022 (3)	−0.008 (3)	−0.001 (3)	0.006 (3)

Geometric parameters (Å, º) top

Ru1—Cl1	2.3521 (17)	C6—C7	1.391 (4)
Ru1—Cl2	2.269 (6)	C7—C8	1.387 (4)
Ru1—N1	2.086 (2)	C8—C9	1.377 (4)
Ru1—N2	2.070 (2)	C9—C10	1.376 (4)
Ru1—N3	2.070 (2)	C11—C12	1.385 (5)
Ru1—N4	2.117 (2)	C12—C13	1.378 (5)
Ru1—C21	1.890 (8)	C13—C14	1.382 (4)
Ru1—C22	1.93 (2)	C14—C15	1.393 (4)
P1—F1	1.597 (2)	C15—C16	1.476 (4)
P1—F2	1.607 (2)	C16—C17	1.394 (4)
P1—F3	1.606 (2)	C17—C18	1.376 (5)
P1—F4	1.600 (2)	C18—C19	1.387 (5)
P1—F5	1.614 (2)	C19—C20	1.382 (5)
P1—F6	1.606 (2)	C1—H1	0.950
O1—C21	1.138 (9)	C2—H2	0.950
O2—C22	1.18 (2)	C3—H3	0.950
N1—C1	1.339 (4)	C4—H4	0.950
N1—C5	1.363 (4)	C7—H5	0.950
N2—C6	1.362 (4)	C8—H6	0.950
N2—C10	1.344 (4)	C9—H7	0.950
N3—C11	1.341 (4)	C10—H8	0.950
N3—C15	1.368 (4)	C11—H9	0.950
N4—C16	1.353 (4)	C12—H10	0.950
N4—C20	1.334 (4)	C13—H11	0.950
C1—C2	1.380 (5)	C14—H12	0.950
C2—C3	1.383 (5)	C17—H13	0.950
C3—C4	1.388 (5)	C18—H14	0.950
C4—C5	1.391 (4)	C19—H15	0.950
C5—C6	1.474 (4)	C20—H16	0.950

Cl1—Ru1—N1	176.52 (9)	C4—C5—C6	123.7 (3)
Cl1—Ru1—N2	97.47 (8)	N2—C6—C5	115.4 (2)
Cl1—Ru1—N3	86.91 (8)	N2—C6—C7	121.3 (2)
Cl1—Ru1—N4	91.41 (8)	C5—C6—C7	123.3 (2)
Cl1—Ru1—C21	90.3 (2)	C6—C7—C8	118.6 (3)
Cl2—Ru1—N1	93.18 (18)	C7—C8—C9	119.7 (3)
Cl2—Ru1—N2	86.45 (17)	C8—C9—C10	119.1 (3)
Cl2—Ru1—N3	102.85 (17)	N2—C10—C9	122.3 (2)
Cl2—Ru1—N4	177.80 (17)	N3—C11—C12	122.5 (3)
Cl2—Ru1—C22	90.0 (6)	C11—C12—C13	119.0 (3)
N1—Ru1—N2	79.12 (11)	C12—C13—C14	119.5 (3)
N1—Ru1—N3	96.35 (11)	C13—C14—C15	119.3 (3)
N1—Ru1—N4	88.06 (10)	N3—C15—C14	121.0 (2)
N1—Ru1—C21	90.4 (2)	N3—C15—C16	115.8 (2)
N1—Ru1—C22	173.1 (7)	C14—C15—C16	123.2 (3)
N2—Ru1—N3	169.95 (10)	N4—C16—C15	115.7 (2)
N2—Ru1—N4	92.01 (11)	N4—C16—C17	120.7 (3)
N2—Ru1—C21	90.8 (2)	C15—C16—C17	123.6 (3)
N2—Ru1—C22	95.0 (7)	C16—C17—C18	119.7 (3)
N3—Ru1—N4	78.80 (10)	C17—C18—C19	119.4 (3)
N3—Ru1—C21	98.3 (2)	C18—C19—C20	117.9 (3)
N3—Ru1—C22	88.9 (7)	N4—C20—C19	123.3 (3)
N4—Ru1—C21	176.5 (2)	Ru1—C21—O1	172.4 (7)
N4—Ru1—C22	88.6 (6)	Ru1—C22—O2	166.8 (18)
F1—P1—F2	179.39 (12)	N1—C1—H1	118.9
F1—P1—F3	89.87 (11)	C2—C1—H1	118.9
F1—P1—F4	90.40 (13)	C1—C2—H2	120.5
F1—P1—F5	90.64 (13)	C3—C2—H2	120.5
F1—P1—F6	89.76 (11)	C2—C3—H3	120.4
F2—P1—F3	90.16 (11)	C4—C3—H3	120.4
F2—P1—F4	90.20 (12)	C3—C4—H4	120.4
F2—P1—F5	89.32 (12)	C5—C4—H4	120.4
F2—P1—F6	89.63 (10)	C6—C7—H5	120.7
F3—P1—F4	90.14 (10)	C8—C7—H5	120.7
F3—P1—F5	179.47 (13)	C7—C8—H6	120.1
F3—P1—F6	90.31 (11)	C9—C8—H6	120.1
F4—P1—F5	89.96 (11)	C8—C9—H7	120.4
F4—P1—F6	179.52 (12)	C10—C9—H7	120.4
F5—P1—F6	89.58 (11)	N2—C10—H8	118.9
Ru1—N1—C1	126.0 (2)	C9—C10—H8	118.9
Ru1—N1—C5	114.6 (2)	N3—C11—H9	118.8
C1—N1—C5	119.4 (2)	C12—C11—H9	118.7
Ru1—N2—C6	115.2 (2)	C11—C12—H10	120.5
Ru1—N2—C10	125.6 (2)	C13—C12—H10	120.5
C6—N2—C10	118.9 (2)	C12—C13—H11	120.3
Ru1—N3—C11	126.0 (2)	C14—C13—H11	120.3
Ru1—N3—C15	115.3 (2)	C13—C14—H12	120.3
C11—N3—C15	118.7 (2)	C15—C14—H12	120.3
Ru1—N4—C16	114.4 (2)	C16—C17—H13	120.1
Ru1—N4—C20	126.7 (2)	C18—C17—H13	120.2
C16—N4—C20	118.9 (2)	C17—C18—H14	120.3
N1—C1—C2	122.3 (3)	C19—C18—H14	120.3
C1—C2—C3	119.1 (3)	C18—C19—H15	121.1
C2—C3—C4	119.3 (3)	C20—C19—H15	121.1
C3—C4—C5	119.3 (3)	N4—C20—H16	118.3
N1—C5—C4	120.7 (3)	C19—C20—H16	118.3
N1—C5—C6	115.5 (2)

Cl1—Ru1—N2—C6	176.6 (2)	C22—Ru1—N3—C11	92.0 (7)
Cl1—Ru1—N2—C10	3.3 (2)	C22—Ru1—N3—C15	−87.8 (6)
Cl1—Ru1—N3—C11	88.8 (2)	N4—Ru1—C22—Cl1	−137 (12)
Cl1—Ru1—N3—C15	−91.0 (2)	N4—Ru1—C22—O2	−180 (8)
N3—Ru1—Cl1—O2	−150 (3)	C22—Ru1—N4—C16	88.3 (8)
N3—Ru1—Cl1—C22	121 (12)	C22—Ru1—N4—C20	−93.7 (8)
Cl1—Ru1—N4—C16	85.7 (2)	Ru1—N1—C1—C2	177.8 (2)
Cl1—Ru1—N4—C20	−96.2 (2)	Ru1—N1—C5—C4	−177.4 (2)
N4—Ru1—Cl1—O2	131 (3)	Ru1—N1—C5—C6	2.2 (3)
C21—Ru1—Cl1—O2	−52 (3)	C1—N1—C5—C4	1.5 (4)
Cl2—Ru1—N1—C1	−92.9 (3)	C1—N1—C5—C6	−178.9 (3)
Cl2—Ru1—N1—C5	85.9 (2)	C5—N1—C1—C2	−1.0 (5)
N1—Ru1—Cl2—O1	76 (3)	Ru1—N2—C6—C5	4.6 (3)
N1—Ru1—Cl2—C21	61 (3)	Ru1—N2—C6—C7	−174.0 (2)
Cl2—Ru1—N2—C6	−96.6 (2)	Ru1—N2—C10—C9	172.8 (2)
Cl2—Ru1—N2—C10	90.0 (3)	C6—N2—C10—C9	−0.3 (5)
N2—Ru1—Cl2—O1	155 (3)	C10—N2—C6—C5	178.5 (3)
N2—Ru1—Cl2—C21	139 (3)	C10—N2—C6—C7	−0.2 (4)
Cl2—Ru1—N3—C11	2.3 (3)	Ru1—N3—C11—C12	−179.3 (2)
Cl2—Ru1—N3—C15	−177.5 (2)	Ru1—N3—C15—C14	179.6 (2)
N3—Ru1—Cl2—O1	−21 (3)	Ru1—N3—C15—C16	−1.0 (3)
N3—Ru1—Cl2—C21	−37 (3)	C11—N3—C15—C14	−0.2 (4)
Cl2—Ru1—C22—O2	2 (5)	C11—N3—C15—C16	179.2 (2)
N1—Ru1—N2—C6	−2.7 (2)	C15—N3—C11—C12	0.5 (5)
N1—Ru1—N2—C10	−176.0 (2)	Ru1—N4—C16—C15	0.6 (3)
N2—Ru1—N1—C1	−178.6 (2)	Ru1—N4—C16—C17	179.7 (2)
N2—Ru1—N1—C5	0.2 (2)	Ru1—N4—C20—C19	−177.9 (2)
N1—Ru1—N3—C11	−92.4 (2)	C16—N4—C20—C19	0.1 (3)
N1—Ru1—N3—C15	87.8 (2)	C20—N4—C16—C15	−177.6 (2)
N3—Ru1—N1—C1	10.4 (2)	C20—N4—C16—C17	1.5 (4)
N3—Ru1—N1—C5	−170.8 (2)	N1—C1—C2—C3	0.2 (4)
N1—Ru1—N4—C16	−97.8 (2)	C1—C2—C3—C4	0.1 (4)
N1—Ru1—N4—C20	80.3 (2)	C2—C3—C4—C5	0.4 (5)
N4—Ru1—N1—C1	88.9 (2)	C3—C4—C5—N1	−1.2 (5)
N4—Ru1—N1—C5	−92.3 (2)	C3—C4—C5—C6	179.3 (3)
C21—Ru1—N1—C1	−87.9 (3)	N1—C5—C6—N2	−4.5 (4)
C21—Ru1—N1—C5	90.9 (3)	N1—C5—C6—C7	174.1 (3)
N2—Ru1—N3—C11	−155.0 (5)	C4—C5—C6—N2	175.1 (3)
N2—Ru1—N3—C15	25.2 (7)	C4—C5—C6—C7	−6.3 (5)
N3—Ru1—N2—C6	61.3 (6)	N2—C6—C7—C8	1.5 (5)
N3—Ru1—N2—C10	−112.1 (5)	C5—C6—C7—C8	−177.0 (3)
N2—Ru1—N4—C16	−176.8 (2)	C6—C7—C8—C9	−2.4 (4)
N2—Ru1—N4—C20	1.3 (2)	C7—C8—C9—C10	2.0 (5)
N4—Ru1—N2—C6	85.0 (2)	C8—C9—C10—N2	−0.6 (5)
N4—Ru1—N2—C10	−88.4 (2)	N3—C11—C12—C13	−0.5 (5)
N2—Ru1—C21—Cl2	−41 (3)	C11—C12—C13—C14	0.2 (4)
C21—Ru1—N2—C6	−92.9 (3)	C12—C13—C14—C15	0.1 (3)
C21—Ru1—N2—C10	93.7 (3)	C13—C14—C15—N3	−0.1 (3)
N2—Ru1—C22—O2	89 (9)	C13—C14—C15—C16	−179.4 (3)
C22—Ru1—N2—C6	173.7 (7)	N3—C15—C16—N4	0.3 (4)
C22—Ru1—N2—C10	0.4 (7)	N3—C15—C16—C17	−178.8 (3)
N3—Ru1—N4—C16	−0.9 (2)	C14—C15—C16—N4	179.6 (3)
N3—Ru1—N4—C20	177.2 (2)	C14—C15—C16—C17	0.5 (5)
N4—Ru1—N3—C11	−179.2 (2)	N4—C16—C17—C18	−1.6 (5)
N4—Ru1—N3—C15	1.0 (2)	C15—C16—C17—C18	177.4 (3)
C21—Ru1—N3—C11	−1.1 (3)	C16—C17—C18—C19	0.1 (4)
C21—Ru1—N3—C15	179.1 (3)	C17—C18—C19—C20	1.4 (5)
N3—Ru1—C22—O2	−101 (9)	C18—C19—C20—N4	−1.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F2ⁱ	0.95	2.46	3.166 (4)	131
C4—H4···F1ⁱⁱ	0.95	2.41	3.257 (4)	148
C7—H5···F1ⁱⁱ	0.95	2.54	3.431 (4)	156
C8—H6···F2ⁱⁱⁱ	0.95	2.50	3.265 (4)	138
C13—H11···F5^iv	0.95	2.39	3.331 (4)	168

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

Experimental details

Crystal data
Chemical formula	[RuCl(C₁₀H₈N₂)₂(CO)]·PF₆
M_r	621.87
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	93
a, b, c (Å)	10.882 (5), 12.063 (5), 17.410 (7)
V (Å³)	2285.2 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.20 × 0.10 × 0.02

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.897, 0.981
No. of measured, independent and observed [F² > 2σ(F²)] reflections	22875, 5177, 4689
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.062, 1.08
No. of reflections	5177
No. of parameters	330
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.37, −1.28
Absolute structure	Flack (1983), 2249 Friedel pairs
Absolute structure parameter	0.22 (4)

Computer programs: CrystalClear-SM (Rigaku, 2009), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), CrystalStructure (Rigaku, 2006).

Selected bond lengths (Å) top

Ru1—Cl1	2.3521 (17)	Ru1—N3	2.070 (2)
Ru1—N1	2.086 (2)	Ru1—N4	2.117 (2)
Ru1—N2	2.070 (2)	Ru1—C21	1.890 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F2ⁱ	0.95	2.46	3.166 (4)	131
C4—H4···F1ⁱⁱ	0.95	2.41	3.257 (4)	148
C7—H5···F1ⁱⁱ	0.95	2.54	3.431 (4)	156
C8—H6···F2ⁱⁱⁱ	0.95	2.50	3.265 (4)	138
C13—H11···F5^iv	0.95	2.39	3.331 (4)	168

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

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, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Clear, J. M., Kelly, J. M. O., Connell, C. M., Vos, J. G., Cardin, C. J., Costa, S. R. & Edwards, A. J. (1980). J. Chem. Soc. Chem. Commun. pp. 750–751. CrossRef Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ishida, H., Tanaka, K., Morimoto, M. & Tanaka, T. (1986). Organometallics, 5, 724–730. CrossRef CAS Web of Science Google Scholar
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. Google Scholar
Lehn, J.-M. & Ziessel, R. (1990). J. Organomet. Chem. 382, 157–173. CrossRef CAS Web of Science Google Scholar
Oyama, D., Suzuki, K., Yamanaka, T. & Takase, T. (2012). J. Coord. Chem. 65, 78–86. Web of Science CSD CrossRef CAS Google Scholar
Rigaku (2006). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2009). CrystalClear-SM. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 1| January 2013| Pages m1-m2

https://doi.org/10.1107/S1600536812048246

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)