[1-tert-Butyl-3-(pyridin-2-ylmethyl-κN)imidazol-2-yl­idene-κC1]carbonyl­dichlorido(dimethyl sulfoxide-κS)ruthenium(II)

Cheng, Y.; Hua, W.-Q.; Zhou, Y.-H.

doi:10.1107/S1600536811042590

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1573

doi:10.1107/S1600536811042590

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[1-tert-Butyl-3-(pyridin-2-ylmethyl-κN)imidazol-2-ylidene-κC¹]carbonyldichlorido(dimethyl sulfoxide-κS)ruthenium(II)

Yong Cheng,^a ^* Wen-Qian Hua ^a and Ying-Hua Zhou ^a

^aCollege of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, People's Republic of China
^*Correspondence e-mail: chyong2008happy@163.com

(Received 3 July 2011; accepted 14 October 2011; online 22 October 2011)

In the title complex, [RuCl₂(C₁₃H₁₇N₃)(C₂H₆OS)(CO)], the coordination environment around the Ru atom is slightly distorted octahedral. The Cl atoms are mutually trans to the dimethyl sulfoxide ligand and the imidazole carbene C atom, respectively. The carbonyl ligand is located trans to the pyridine N atom.

Related literature

For general background to N-heterocyclic carbene (NHC) complexes, see: Hahn et al. (2006 ); Lee et al. (2007 ); Mas-Marza et al. (2005 ); Kaufhold et al. (2008 ); Araki et al. (2008 ); Son et al. (2004 ); Poyatos et al. (2006 ). For our previous work on Ru–NHC complexes, see: Cheng, Sun et al. (2009 ); Cheng, Xu et al. (2009 ).

Experimental

Crystal data

[RuCl₂(C₁₃H₁₇N₃)(C₂H₆OS)(CO)]
M_r = 493.40
Orthorhombic, P b c a
a = 14.3297 (14) Å
b = 15.7428 (16) Å
c = 17.1867 (16) Å
V = 3877.1 (7) Å³
Z = 8
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 291 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.74, T_max = 0.79
20132 measured reflections
3815 independent reflections
3401 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.06
3815 reflections
231 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −1.30 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042590/zb2017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042590/zb2017Isup2.hkl

checkCIF report

Comment top

N-Heterocyclic carbenes (NHCs) complexes have attracted increasing attention as they have been proven to act as efficient homogeneous catalyst (Hahn et al. 2006). Pyridine-functionalized bidentate carbene ligands have been frequently used as versatile ancillary ligands in organometallic complexes in recent years (Lee et al. 2007). A lot of bidentate pyridinefunctionalized NHC complexes have been prepared, some of which showed catalytic activities in reactions such as hydrosilylation of acetylenes, cyclization of acetylenic carboxylic acids, hydrogen transfer to ketones (Mas-Marza et al. 2005). However, few reports have been published on Ru complexes containing bidentate pyridine-functionalized NHC ligands (Kaufhold et al. 2008, Araki et al. 2008, Son et al. 2004, Poyatos et al. 2006). We have reported the synthesis and characterization of pyridine functionalized Ru(II)-NHC nitrosyl or carbonyl complexes and their catalytic activity in hydrogen transfer of ketones (Cheng, Sun et al., 2009; Cheng, Xu et al., 2009). Herein, we report a new pyridine functionalized Ru-NHC carbonyl complex with dimethyl sulfoxide.

The structure of the title complex shows that the coordination geometry around the ruthenium atom can be rationalized as a slightly distorted octahedron. Two chloride atoms occupy mutually trans to the dimethylsulfoxide and imidazole carbene carbon respectively. The CO group is located trans to the pyridine nitrogen (Fig.1).

Related literature top

For general background to N-Heterocyclic carbene (NHC) complexes, see: Hahn et al. (2006); Lee et al. (2007); Mas-Marza et al. (2005); Kaufhold et al. (2008); Araki et al. (2008); Son et al. (2004); Poyatos et al. (2006). For our previous work on Ru–NHC complexes, see: Cheng, Sun et al. (2009); Cheng, Xu et al. (2009).

Experimental top

A mixture of 3-tert-butyl-1-picolylimidazolium Bromide (1.0 mmol), silver oxide (1.0 mmol) and CH₂Cl₂ (30 ml) was stirred at room temperature for 12 h, and was then filtered through Celite to remove unreacted silver oxide and insoluble residues. [Ru(CO)₂Cl₂]_n (1.0 mmol) was added to the pale yellow solution, stirred for 12 h at room temperature and then filtered through Celite to remove the silver halide. The products were chromatographed using silica gel. Elution with CH₂Cl₂: MeOH (40:1) afforded a pale yellow band that contained the trans-[(3-tert-butyl-1-picolylimidazol-2-ylidene)biscolorodicarbonylruthenium], Removal of the volatiles under vacuum gave the products as pale yellow powders.

Exposured the saturated dimethyl sulfoxide solution of the trans-[(3-tert-butyl-1-picolylimidazol-2-ylidene)biscolorodicarbonylruthenium] in air, yellow-rectangle crystals were obtained one month later, which were title complex confirmed by X-ray structure determination. It shows that dimethyl sulfoxide displaced one molecule of CO in previous compound, and the structure converted from trans to cis.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title complex showing 30% probability ellipsoids. Hydrogen atoms are omitted for clarity.[symmetry codes: (i)'-x + 1/2, -y, z + 1/2' (ii)'-x, y + 1/2, -z + 1/2']

[1-tert-Butyl-3-(pyridin-2-ylmethyl-κN)imidazol-2- ylidene-κC¹]carbonyldichlorido(dimethyl sulfoxide-κS)ruthenium(II) top

Crystal data top

[RuCl₂(C₁₃H₁₇N₃)(C₂H₆OS)(CO)]	F(000) = 2000
M_r = 493.40	D_x = 1.691 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2216 reflections
a = 14.3297 (14) Å	θ = 2.3–23.2°
b = 15.7428 (16) Å	µ = 1.21 mm⁻¹
c = 17.1867 (16) Å	T = 291 K
V = 3877.1 (7) Å³	Cuboid, yellow
Z = 8	0.26 × 0.22 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3815 independent reflections
Radiation source: sealed tube	3401 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
phi and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→17
T_min = 0.74, T_max = 0.79	k = −12→19
20132 measured reflections	l = −17→21

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.07P)² + 1.99P] where P = (F_o² + 2F_c²)/3
3815 reflections	(Δ/σ)_max < 0.001
231 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −1.30 e Å⁻³

Crystal data top

[RuCl₂(C₁₃H₁₇N₃)(C₂H₆OS)(CO)]	V = 3877.1 (7) Å³
M_r = 493.40	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.3297 (14) Å	µ = 1.21 mm⁻¹
b = 15.7428 (16) Å	T = 291 K
c = 17.1867 (16) Å	0.26 × 0.22 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3815 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3401 reflections with I > 2σ(I)
T_min = 0.74, T_max = 0.79	R_int = 0.044
20132 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
3815 reflections	Δρ_min = −1.30 e Å⁻³
231 parameters

Special details top

Experimental. The single crystals was mounted on a glass fibre with silicon grease. Diffraction data were collected on a Bruker SMART Apex CCD diffractometer using graphite-monochromated MoKa (l =0.71073 Å) radiation and corrllected for absorption using SADABS program.

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
C1	0.7924 (2)	0.1922 (3)	0.4198 (2)	0.0412 (8)
H1	0.7884	0.1378	0.4404	0.049*
C2	0.8640 (3)	0.2469 (3)	0.4455 (3)	0.0460 (10)
H2	0.9069	0.2292	0.4827	0.055*
C3	0.8685 (3)	0.3279 (3)	0.4137 (3)	0.0504 (10)
H3	0.9157	0.3649	0.4291	0.060*
C4	0.8029 (2)	0.3541 (2)	0.3591 (2)	0.0374 (8)
H4	0.8046	0.4085	0.3380	0.045*
C5	0.7357 (2)	0.2968 (2)	0.33735 (19)	0.0307 (7)
C6	0.6614 (3)	0.3243 (2)	0.2791 (2)	0.0389 (8)
H6A	0.6010	0.3249	0.3047	0.047*
H6B	0.6748	0.3817	0.2617	0.047*
C7	0.6571 (3)	0.3016 (3)	0.1371 (2)	0.0487 (10)
H7	0.6625	0.3586	0.1233	0.058*
C8	0.6478 (3)	0.2344 (3)	0.0883 (2)	0.0485 (10)
H8	0.6465	0.2366	0.0343	0.058*
C9	0.6444 (2)	0.1815 (2)	0.21162 (19)	0.0276 (6)
C10	0.6203 (3)	0.0776 (3)	0.0934 (2)	0.0403 (8)
C11	0.6801 (3)	0.0038 (3)	0.1278 (3)	0.0501 (10)
H11A	0.7451	0.0162	0.1208	0.075*
H11B	0.6650	−0.0483	0.1016	0.075*
H11C	0.6670	−0.0020	0.1824	0.075*
C12	0.5139 (3)	0.0597 (3)	0.1032 (3)	0.0512 (10)
H12A	0.4976	0.0628	0.1573	0.077*
H12B	0.4998	0.0040	0.0837	0.077*
H12C	0.4789	0.1013	0.0746	0.077*
C13	0.6446 (3)	0.0843 (3)	0.0066 (2)	0.0577 (12)
H13A	0.6002	0.1206	−0.0188	0.087*
H13B	0.6425	0.0288	−0.0166	0.087*
H13C	0.7061	0.1076	0.0008	0.087*
C14	0.4160 (3)	0.1148 (3)	0.3901 (3)	0.0518 (11)
H14A	0.4441	0.0782	0.4280	0.078*
H14B	0.3913	0.0812	0.3482	0.078*
H14C	0.3664	0.1466	0.4139	0.078*
C15	0.4341 (3)	0.2282 (3)	0.2722 (3)	0.0524 (10)
H15A	0.3793	0.2559	0.2920	0.079*
H15B	0.4158	0.1823	0.2387	0.079*
H15C	0.4709	0.2682	0.2433	0.079*
C16	0.5656 (2)	0.0265 (2)	0.2880 (2)	0.0351 (7)
Cl1	0.78532 (6)	0.05000 (6)	0.29450 (6)	0.0388 (2)
Cl2	0.63074 (7)	0.05755 (7)	0.44994 (6)	0.0496 (3)
N1	0.72873 (19)	0.21741 (17)	0.36515 (15)	0.0303 (6)
N2	0.65692 (19)	0.26818 (19)	0.21148 (17)	0.0325 (6)
N3	0.6403 (2)	0.1616 (2)	0.13376 (18)	0.0364 (7)
O1	0.5227 (2)	−0.03364 (19)	0.27652 (19)	0.0556 (8)
O2	0.51299 (19)	0.25707 (19)	0.40880 (16)	0.0488 (7)
Ru1	0.636122 (18)	0.119715 (16)	0.318107 (15)	0.02810 (12)
S1	0.50232 (6)	0.18683 (6)	0.35263 (5)	0.0356 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0356 (18)	0.053 (2)	0.0345 (18)	0.0042 (16)	−0.0116 (14)	−0.0115 (16)
C2	0.041 (2)	0.047 (2)	0.050 (2)	−0.0011 (16)	−0.0079 (16)	−0.0176 (19)
C3	0.043 (2)	0.054 (2)	0.054 (3)	−0.0021 (18)	−0.0030 (17)	−0.020 (2)
C4	0.0343 (17)	0.0377 (19)	0.0402 (19)	−0.0088 (15)	0.0031 (14)	−0.0128 (16)
C5	0.0319 (16)	0.0288 (16)	0.0316 (16)	0.0009 (13)	0.0054 (13)	−0.0038 (13)
C6	0.0436 (19)	0.0327 (18)	0.040 (2)	0.0098 (15)	−0.0052 (16)	−0.0053 (15)
C7	0.056 (2)	0.049 (2)	0.041 (2)	−0.0112 (19)	−0.0021 (18)	0.0076 (18)
C8	0.066 (3)	0.044 (2)	0.036 (2)	−0.0120 (19)	−0.0048 (18)	0.0055 (17)
C9	0.0219 (15)	0.0351 (17)	0.0259 (16)	−0.0020 (12)	−0.0013 (11)	−0.0008 (13)
C10	0.0396 (19)	0.051 (2)	0.0300 (18)	−0.0049 (17)	−0.0043 (14)	−0.0075 (16)
C11	0.035 (2)	0.051 (2)	0.064 (3)	0.0041 (17)	−0.0020 (18)	−0.010 (2)
C12	0.034 (2)	0.063 (3)	0.057 (2)	0.0003 (18)	−0.0081 (17)	−0.010 (2)
C13	0.068 (3)	0.075 (3)	0.030 (2)	−0.009 (2)	0.0055 (18)	−0.010 (2)
C14	0.037 (2)	0.063 (3)	0.055 (3)	−0.0163 (18)	0.0153 (18)	−0.011 (2)
C15	0.035 (2)	0.066 (3)	0.057 (2)	0.0095 (18)	−0.0167 (18)	−0.002 (2)
C16	0.0285 (16)	0.0331 (18)	0.0437 (19)	−0.0018 (14)	−0.0075 (14)	0.0018 (15)
Cl1	0.0302 (4)	0.0355 (4)	0.0508 (5)	0.0019 (3)	−0.0024 (3)	−0.0006 (4)
Cl2	0.0601 (6)	0.0520 (6)	0.0366 (5)	−0.0054 (4)	−0.0026 (4)	0.0137 (4)
N1	0.0292 (14)	0.0306 (14)	0.0309 (14)	0.0006 (11)	−0.0028 (10)	−0.0047 (11)
N2	0.0327 (14)	0.0343 (15)	0.0306 (14)	−0.0040 (12)	−0.0035 (11)	0.0037 (12)
N3	0.0383 (16)	0.0379 (16)	0.0331 (16)	−0.0044 (12)	−0.0029 (11)	−0.0039 (13)
O1	0.0553 (17)	0.0423 (16)	0.069 (2)	−0.0183 (14)	−0.0067 (15)	−0.0039 (14)
O2	0.0422 (14)	0.0581 (17)	0.0462 (15)	−0.0040 (13)	0.0044 (12)	−0.0214 (13)
Ru1	0.02643 (17)	0.02881 (18)	0.02905 (18)	−0.00223 (10)	−0.00179 (9)	0.00097 (10)
S1	0.0285 (4)	0.0435 (5)	0.0348 (4)	−0.0005 (3)	0.0018 (3)	−0.0040 (4)

Geometric parameters (Å, º) top

C1—N1	1.368 (4)	C10—C12	1.560 (5)
C1—C2	1.409 (5)	C11—H11A	0.9600
C1—H1	0.9300	C11—H11B	0.9600
C2—C3	1.389 (6)	C11—H11C	0.9600
C2—H2	0.9300	C12—H12A	0.9600
C3—C4	1.391 (6)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
C4—C5	1.372 (5)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—N1	1.341 (4)	C13—H13C	0.9600
C5—C6	1.526 (5)	C14—S1	1.797 (4)
C6—N2	1.461 (4)	C14—H14A	0.9600
C6—H6A	0.9700	C14—H14B	0.9600
C6—H6B	0.9700	C14—H14C	0.9600
C7—C8	1.357 (6)	C15—S1	1.815 (4)
C7—N2	1.383 (5)	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—N3	1.391 (5)	C15—H15C	0.9600
C8—H8	0.9300	C16—O1	1.146 (4)
C9—N2	1.376 (4)	C16—Ru1	1.855 (3)
C9—N3	1.376 (5)	Cl1—Ru1	2.4372 (9)
C9—Ru1	2.076 (3)	Cl2—Ru1	2.4692 (10)
C10—N3	1.521 (5)	N1—Ru1	2.186 (3)
C10—C13	1.536 (5)	O2—S1	1.476 (3)
C10—C11	1.560 (6)	Ru1—S1	2.2682 (9)

N1—C1—C2	121.6 (4)	C10—C13—H13B	109.5
N1—C1—H1	119.2	H13A—C13—H13B	109.5
C2—C1—H1	119.2	C10—C13—H13C	109.5
C3—C2—C1	118.1 (4)	H13A—C13—H13C	109.5
C3—C2—H2	120.9	H13B—C13—H13C	109.5
C1—C2—H2	120.9	S1—C14—H14A	109.5
C2—C3—C4	120.4 (4)	S1—C14—H14B	109.5
C2—C3—H3	119.8	H14A—C14—H14B	109.5
C4—C3—H3	119.8	S1—C14—H14C	109.5
C5—C4—C3	117.5 (4)	H14A—C14—H14C	109.5
C5—C4—H4	121.2	H14B—C14—H14C	109.5
C3—C4—H4	121.2	S1—C15—H15A	109.5
N1—C5—C4	124.7 (3)	S1—C15—H15B	109.5
N1—C5—C6	116.5 (3)	H15A—C15—H15B	109.5
C4—C5—C6	118.8 (3)	S1—C15—H15C	109.5
N2—C6—C5	112.4 (3)	H15A—C15—H15C	109.5
N2—C6—H6A	109.1	H15B—C15—H15C	109.5
C5—C6—H6A	109.1	O1—C16—Ru1	173.5 (3)
N2—C6—H6B	109.1	C5—N1—C1	117.7 (3)
C5—C6—H6B	109.1	C5—N1—Ru1	124.7 (2)
H6A—C6—H6B	107.9	C1—N1—Ru1	117.1 (2)
C8—C7—N2	105.9 (4)	C9—N2—C7	112.3 (3)
C8—C7—H7	127.1	C9—N2—C6	127.2 (3)
N2—C7—H7	127.1	C7—N2—C6	120.3 (3)
C7—C8—N3	107.7 (4)	C9—N3—C8	110.8 (3)
C7—C8—H8	126.2	C9—N3—C10	130.5 (3)
N3—C8—H8	126.2	C8—N3—C10	118.4 (3)
N2—C9—N3	103.3 (3)	C16—Ru1—C9	98.96 (14)
N2—C9—Ru1	118.3 (2)	C16—Ru1—N1	171.94 (13)
N3—C9—Ru1	138.4 (3)	C9—Ru1—N1	87.79 (11)
N3—C10—C13	109.9 (3)	C16—Ru1—S1	88.94 (11)
N3—C10—C11	111.8 (3)	C9—Ru1—S1	93.48 (9)
C13—C10—C11	107.2 (3)	N1—Ru1—S1	95.09 (7)
N3—C10—C12	107.0 (3)	C16—Ru1—Cl1	94.29 (11)
C13—C10—C12	109.8 (3)	C9—Ru1—Cl1	90.81 (9)
C11—C10—C12	111.2 (3)	N1—Ru1—Cl1	81.13 (7)
C10—C11—H11A	109.5	S1—Ru1—Cl1	174.18 (3)
C10—C11—H11B	109.5	C16—Ru1—Cl2	85.74 (12)
H11A—C11—H11B	109.5	C9—Ru1—Cl2	175.13 (10)
C10—C11—H11C	109.5	N1—Ru1—Cl2	87.62 (8)
H11A—C11—H11C	109.5	S1—Ru1—Cl2	85.31 (4)
H11B—C11—H11C	109.5	Cl1—Ru1—Cl2	90.09 (3)
C10—C12—H12A	109.5	O2—S1—C14	108.05 (19)
C10—C12—H12B	109.5	O2—S1—C15	106.6 (2)
H12A—C12—H12B	109.5	C14—S1—C15	97.4 (2)
C10—C12—H12C	109.5	O2—S1—Ru1	115.63 (11)
H12A—C12—H12C	109.5	C14—S1—Ru1	112.44 (15)
H12B—C12—H12C	109.5	C15—S1—Ru1	115.05 (15)
C10—C13—H13A	109.5

N1—C1—C2—C3	0.0 (6)	C13—C10—N3—C8	19.2 (5)
C1—C2—C3—C4	1.0 (6)	C11—C10—N3—C8	138.1 (4)
C2—C3—C4—C5	−1.1 (6)	C12—C10—N3—C8	−99.9 (4)
C3—C4—C5—N1	0.1 (5)	N2—C9—Ru1—C16	153.9 (2)
C3—C4—C5—C6	178.5 (3)	N3—C9—Ru1—C16	−25.5 (4)
N1—C5—C6—N2	−56.8 (4)	N2—C9—Ru1—N1	−30.6 (2)
C4—C5—C6—N2	124.7 (3)	N3—C9—Ru1—N1	150.1 (3)
N2—C7—C8—N3	1.1 (5)	N2—C9—Ru1—S1	64.4 (2)
C4—C5—N1—C1	0.9 (5)	N3—C9—Ru1—S1	−115.0 (3)
C6—C5—N1—C1	−177.5 (3)	N2—C9—Ru1—Cl1	−111.7 (2)
C4—C5—N1—Ru1	−170.0 (3)	N3—C9—Ru1—Cl1	69.0 (3)
C6—C5—N1—Ru1	11.6 (4)	C5—N1—Ru1—C9	26.9 (3)
C2—C1—N1—C5	−0.9 (5)	C1—N1—Ru1—C9	−144.0 (3)
C2—C1—N1—Ru1	170.7 (3)	C5—N1—Ru1—S1	−66.4 (3)
N3—C9—N2—C7	2.2 (4)	C1—N1—Ru1—S1	122.7 (2)
Ru1—C9—N2—C7	−177.3 (3)	C5—N1—Ru1—Cl1	118.1 (3)
N3—C9—N2—C6	176.7 (3)	C1—N1—Ru1—Cl1	−52.9 (2)
Ru1—C9—N2—C6	−2.8 (4)	C5—N1—Ru1—Cl2	−151.5 (3)
C8—C7—N2—C9	−2.1 (4)	C1—N1—Ru1—Cl2	37.6 (2)
C8—C7—N2—C6	−177.0 (3)	C16—Ru1—S1—O2	158.69 (19)
C5—C6—N2—C9	55.1 (5)	C9—Ru1—S1—O2	−102.40 (17)
C5—C6—N2—C7	−130.8 (4)	N1—Ru1—S1—O2	−14.31 (16)
N2—C9—N3—C8	−1.5 (4)	Cl2—Ru1—S1—O2	72.87 (15)
Ru1—C9—N3—C8	177.9 (3)	C16—Ru1—S1—C14	33.9 (2)
N2—C9—N3—C10	−174.9 (3)	C9—Ru1—S1—C14	132.85 (19)
Ru1—C9—N3—C10	4.5 (6)	N1—Ru1—S1—C14	−139.06 (19)
C7—C8—N3—C9	0.3 (5)	Cl2—Ru1—S1—C14	−51.88 (17)
C7—C8—N3—C10	174.6 (3)	C16—Ru1—S1—C15	−76.3 (2)
C13—C10—N3—C9	−167.8 (3)	C9—Ru1—S1—C15	22.6 (2)
C11—C10—N3—C9	−48.9 (5)	N1—Ru1—S1—C15	110.71 (19)
C12—C10—N3—C9	73.0 (5)	Cl2—Ru1—S1—C15	−162.11 (18)

Experimental details

Crystal data
Chemical formula	[RuCl₂(C₁₃H₁₇N₃)(C₂H₆OS)(CO)]
M_r	493.40
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	291
a, b, c (Å)	14.3297 (14), 15.7428 (16), 17.1867 (16)
V (Å³)	3877.1 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.74, 0.79
No. of measured, independent and observed [I > 2σ(I)] reflections	20132, 3815, 3401
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.06
No. of reflections	3815
No. of parameters	231
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −1.30

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National BasicResearch Program of China (No. 2006CB806104 and 2007CB925102). We are also grateful to the Doctoral Startup Foundation of Anhui Normal University.

References

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