[1-tert-Butyl-3-(pyridin-2-ylmethyl-κN)imidazol-2-yl-idene-κC]carbonyl-dichlorido(dimethyl sulfoxide-κS)ruthenium(II).

In the title complex, [RuCl(2)(C(13)H(17)N(3))(C(2)H(6)OS)(CO)], the coordination environment around the Ru atom is slightly distorted octa-hedral. 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 = 493.40

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.06

3815 reflections

231 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042590/zb2017sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[RuCl2(C13H17N3)(C2H6OS)(CO)]	F(000) = 2000
Mr = 493.40	Dx = 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

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

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(Fo2) + (0.07P)2 + 1.99P] where P = (Fo2 + 2Fc2)/3
3815 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −1.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)