A ruthenium(II) complex with p-cymene and (S)-2-(anilinomethyl)pyrrolidine

The title compound, [(S)-2-(anilino­methyl)­pyrrolidine-N,N′]-chloro(η⁶-para-cymene)­ruthenium(II) chloride, [RuCl-(C₁₀H₁₄)(C₁₁H₁₆N₂)]Cl, has been synthesized by the reaction of [RuCl₂(p-cymene)]₂ (p-cymene is para-iso­propyl­toluene) with (S)-2-(anilinomethyl)­pyrrolidine in triethyl­amine/2-propanol. The Ru atom is in a pseudo-tetrahedral environment coordinated by a chloride ligand, the aromatic hydro­carbon is linked in a η⁶ manner and the amine is linked via its two N atoms. The chloride anion is involved in hydrogen bonding with the di­amine moieties through N—H...Cl interactions, with N...Cl distances of 3.273 (4) and 3.352 (4) Å.

Computing details

Data collection: STADI4 (Stoe & Cie, 1996); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Xtal_GX (Hall & du Boulay, 1997).

(I)

Crystal data

[RuCl(C10H14)(C11H16N2)]Cl	Dx = 1.560 Mg m^−3
Mr = 482.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 45 reflections
a = 8.2107 (3) Å	θ = 12.5–18.2°
b = 9.3093 (4) Å	µ = 1.03 mm^−1
c = 26.8707 (9) Å	T = 295 K
V = 2053.89 (13) Å^3	Brick-shaped, yellow
Z = 4	0.63 × 0.39 × 0.24 mm
F(000) = 992

Data collection

STOE STADI4 diffractometer	6503 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 32.5°, θmin = 1.5°
ω scans	h = −12→12
Absorption correction: ψ scan (X-RED; Stoe & Cie, 1996)	k = 0→14
Tmin = 0.466, Tmax = 0.781	l = 0→40
8338 measured reflections	3 standard reflections every 60 min
7328 independent reflections	intensity decay: 5.7%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.142	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo^2) + (0.070P)^2 + 3.P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
7328 reflections	Δρmax = 1.14 e Å^−3
238 parameters	Δρmin = −1.63 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: heavy-atom method	Absolute structure parameter: 0.05 (5)

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.

Mean plane data ex SHELXL97 for molecule (I) ############################################ # None given here for moelcule (I)

Friedels ######## XS reports 4167 unique data and XL reports 7328, so it seems that 3161 reflections have their Friedel pairs included.

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 (Ų)

	x	y	z	Uiso*/Ueq
Ru	0.40413 (4)	0.36500 (3)	0.131187 (11)	0.02365 (8)
Cl1	0.24482 (17)	0.26862 (15)	0.19947 (5)	0.0390 (3)
Cl2	0.70591 (18)	0.07195 (15)	0.03569 (5)	0.0418 (3)
N1A	0.3716 (5)	0.1629 (4)	0.09410 (14)	0.0286 (8)
H1A	0.4574	0.1551	0.0728	0.034*
C2A	0.2218 (6)	0.1614 (4)	0.06162 (17)	0.0299 (9)
H2A	0.2513	0.1880	0.0275	0.036*
C3A	0.1598 (8)	0.0073 (6)	0.0630 (2)	0.0407 (12)
H31A	0.2146	−0.0513	0.0383	0.049*
H32A	0.0432	0.0031	0.0574	0.049*
C4A	0.2026 (7)	−0.0407 (6)	0.1158 (2)	0.0404 (11)
H41A	0.1243	−0.0047	0.1397	0.048*
H42A	0.2072	−0.1446	0.1181	0.048*
C5A	0.3725 (7)	0.0251 (5)	0.1242 (2)	0.0372 (11)
H51A	0.3901	0.0451	0.1592	0.045*
H52A	0.4576	−0.0391	0.1126	0.045*
C6A	0.0988 (7)	0.2666 (5)	0.08200 (18)	0.0318 (8)
H61A	0.0083	0.2765	0.0590	0.038*
H62A	0.0568	0.2327	0.1136	0.038*
N7A	0.1819 (5)	0.4079 (4)	0.08864 (14)	0.0284 (7)
H7A	0.2179	0.4317	0.0577	0.034*
C1F	0.0694 (5)	0.5233 (5)	0.10208 (17)	0.0283 (8)
C2F	0.0011 (7)	0.6062 (5)	0.0644 (2)	0.0380 (11)
H2F	0.0278	0.5883	0.0314	0.046*
C3F	−0.1056 (8)	0.7169 (5)	0.0763 (2)	0.0447 (12)
H3F	−0.1511	0.7720	0.0510	0.054*
C4F	−0.1456 (7)	0.7437 (6)	0.1247 (3)	0.0451 (13)
H4F	−0.2150	0.8194	0.1324	0.054*
C5F	−0.0811 (7)	0.6598 (6)	0.1623 (2)	0.0448 (12)
H5F	−0.1126	0.6755	0.1951	0.054*
C6F	0.0292 (7)	0.5501 (6)	0.1515 (2)	0.0371 (10)
H6F	0.0763	0.4966	0.1769	0.044*
C1T	0.5178 (6)	0.5560 (5)	0.09787 (17)	0.0305 (9)
C2T	0.4798 (7)	0.5857 (5)	0.14851 (17)	0.0325 (9)
H2T	0.4200	0.6672	0.1566	0.039*
C3T	0.5319 (6)	0.4931 (5)	0.18641 (17)	0.0317 (9)
H3T	0.5015	0.5125	0.2191	0.038*
C4T	0.6289 (5)	0.3688 (6)	0.17668 (16)	0.0295 (8)
C5T	0.6678 (5)	0.3416 (5)	0.12656 (18)	0.0306 (9)
H5T	0.7313	0.2620	0.1188	0.037*
C6T	0.6134 (6)	0.4343 (5)	0.08743 (17)	0.0302 (9)
H6T	0.6405	0.4128	0.0547	0.036*
C7T	0.4578 (7)	0.6513 (6)	0.0568 (2)	0.0417 (11)
H71T	0.5339	0.7281	0.0515	0.050*
H72T	0.3538	0.6905	0.0658	0.050*
H73T	0.4470	0.5963	0.0267	0.050*
C8T	0.6785 (7)	0.2729 (7)	0.2195 (2)	0.0409 (11)
H8T	0.5802	0.2512	0.2387	0.049*
C9T	0.7535 (9)	0.1306 (8)	0.2035 (3)	0.0570 (16)
H91T	0.6797	0.0807	0.1819	0.068*
H92T	0.7743	0.0731	0.2325	0.068*
H93T	0.8540	0.1482	0.1863	0.068*
C10T	0.7957 (9)	0.3540 (9)	0.2539 (2)	0.0565 (16)
H01T	0.8114	0.2999	0.2839	0.068*
H02T	0.7507	0.4463	0.2619	0.068*
H03T	0.8985	0.3664	0.2374	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru	0.02573 (13)	0.02137 (12)	0.02384 (12)	−0.00113 (12)	0.00172 (12)	−0.00144 (12)
Cl1	0.0409 (6)	0.0417 (6)	0.0343 (5)	−0.0026 (5)	0.0094 (5)	0.0061 (5)
Cl2	0.0480 (7)	0.0422 (7)	0.0351 (5)	0.0082 (6)	0.0019 (5)	−0.0051 (5)
N1A	0.0303 (19)	0.0234 (17)	0.0319 (17)	−0.0008 (13)	0.0006 (13)	−0.0018 (13)
C2A	0.039 (2)	0.0223 (19)	0.0287 (18)	−0.0006 (16)	−0.0026 (17)	−0.0005 (14)
C3A	0.051 (3)	0.026 (2)	0.045 (3)	−0.004 (2)	−0.008 (2)	−0.004 (2)
C4A	0.046 (3)	0.025 (2)	0.050 (3)	−0.006 (2)	−0.005 (2)	0.0036 (19)
C5A	0.043 (3)	0.0263 (19)	0.042 (3)	0.0003 (18)	−0.006 (2)	0.0008 (18)
C6A	0.030 (2)	0.0254 (18)	0.040 (2)	−0.0012 (19)	−0.005 (2)	−0.0056 (16)
N7A	0.033 (2)	0.0235 (16)	0.0287 (17)	−0.0004 (14)	0.0013 (14)	−0.0020 (13)
C1F	0.025 (2)	0.0239 (18)	0.036 (2)	−0.0021 (15)	0.0003 (16)	−0.0027 (15)
C2F	0.037 (2)	0.030 (2)	0.047 (3)	0.0021 (19)	0.001 (2)	0.0041 (19)
C3F	0.038 (3)	0.027 (2)	0.070 (4)	0.003 (2)	0.002 (3)	0.007 (2)
C4F	0.031 (2)	0.028 (2)	0.076 (4)	0.0027 (18)	0.006 (3)	−0.008 (3)
C5F	0.041 (3)	0.040 (3)	0.053 (3)	0.000 (2)	0.006 (2)	−0.018 (2)
C6F	0.036 (3)	0.037 (2)	0.039 (2)	0.002 (2)	0.002 (2)	−0.005 (2)
C1T	0.033 (2)	0.026 (2)	0.032 (2)	−0.0053 (17)	−0.0001 (17)	−0.0001 (16)
C2T	0.039 (3)	0.0250 (19)	0.033 (2)	−0.0054 (18)	−0.0018 (18)	−0.0058 (17)
C3T	0.037 (2)	0.032 (2)	0.0270 (19)	0.0008 (19)	−0.0019 (17)	−0.0070 (17)
C4T	0.0275 (19)	0.031 (2)	0.0294 (17)	0.0003 (18)	−0.0032 (14)	−0.0022 (18)
C5T	0.0244 (18)	0.031 (2)	0.037 (2)	−0.0026 (15)	0.0008 (16)	−0.0047 (18)
C6T	0.029 (2)	0.031 (2)	0.0310 (19)	−0.0010 (18)	0.0086 (17)	−0.0011 (16)
C7T	0.047 (3)	0.035 (3)	0.043 (3)	−0.007 (2)	−0.004 (2)	0.010 (2)
C8T	0.038 (3)	0.046 (3)	0.039 (2)	0.002 (2)	−0.002 (2)	0.008 (2)
C9T	0.061 (4)	0.044 (3)	0.066 (4)	0.009 (3)	−0.012 (3)	0.009 (3)
C10T	0.065 (4)	0.067 (4)	0.038 (3)	0.008 (4)	−0.015 (3)	0.004 (3)

Geometric parameters (Å, º)

Ru—Cl1	2.4254 (12)	C1F—C2F	1.390 (7)
Ru—N1A	2.146 (4)	C1F—C6F	1.390 (7)
Ru—N7A	2.190 (4)	C2F—C3F	1.389 (7)
Ru—C1T	2.199 (5)	C3F—C4F	1.364 (9)
Ru—C2T	2.196 (5)	C4F—C5F	1.382 (9)
Ru—C3T	2.174 (5)	C5F—C6F	1.395 (8)
Ru—C4T	2.214 (4)	C1T—C6T	1.407 (7)
Ru—C5T	2.179 (4)	C1T—C2T	1.423 (7)
Ru—C6T	2.180 (5)	C1T—C7T	1.500 (7)
N1A—C2A	1.508 (6)	C2T—C3T	1.401 (7)
N1A—C5A	1.517 (6)	C3T—C4T	1.430 (7)
C2A—C6A	1.510 (7)	C4T—C5T	1.407 (6)
C2A—C3A	1.523 (7)	C4T—C8T	1.511 (7)
C3A—C4A	1.527 (8)	C5T—C6T	1.432 (7)
C4A—C5A	1.540 (8)	C8T—C9T	1.523 (9)
C6A—N7A	1.493 (6)	C8T—C10T	1.533 (9)
N7A—C1F	1.463 (6)
N1A—Ru—C3T	149.11 (17)	C2A—C3A—C4A	102.8 (4)
N1A—Ru—C5T	90.53 (16)	C3A—C4A—C5A	103.2 (5)
C3T—Ru—C5T	67.32 (18)	N1A—C5A—C4A	104.7 (4)
N1A—Ru—C6T	96.15 (16)	N7A—C6A—C2A	108.0 (4)
C3T—Ru—C6T	79.95 (19)	C1F—N7A—C6A	112.8 (4)
C5T—Ru—C6T	38.35 (18)	C1F—N7A—Ru	122.1 (3)
N1A—Ru—N7A	79.26 (15)	C6A—N7A—Ru	106.4 (3)
C3T—Ru—N7A	131.19 (17)	C2F—C1F—C6F	120.0 (4)
C5T—Ru—N7A	144.69 (16)	C2F—C1F—N7A	118.9 (4)
C6T—Ru—N7A	108.73 (16)	C6F—C1F—N7A	121.2 (4)
N1A—Ru—C2T	162.52 (16)	C3F—C2F—C1F	120.0 (5)
C3T—Ru—C2T	37.39 (18)	C4F—C3F—C2F	120.4 (5)
C5T—Ru—C2T	79.90 (19)	C3F—C4F—C5F	120.1 (5)
C6T—Ru—C2T	67.32 (19)	C4F—C5F—C6F	120.7 (5)
N7A—Ru—C2T	100.13 (17)	C1F—C6F—C5F	118.9 (5)
N1A—Ru—C1T	124.95 (16)	C6T—C1T—C2T	118.0 (4)
C3T—Ru—C1T	68.24 (18)	C6T—C1T—C7T	120.8 (4)
C5T—Ru—C1T	68.66 (18)	C2T—C1T—C7T	121.2 (5)
C6T—Ru—C1T	37.48 (18)	C6T—C1T—Ru	70.5 (3)
N7A—Ru—C1T	89.64 (17)	C2T—C1T—Ru	71.0 (3)
C2T—Ru—C1T	37.78 (18)	C7T—C1T—Ru	129.7 (4)
N1A—Ru—C4T	111.96 (17)	C3T—C2T—C1T	120.6 (5)
C3T—Ru—C4T	38.01 (18)	C3T—C2T—Ru	70.4 (3)
C5T—Ru—C4T	37.34 (16)	C1T—C2T—Ru	71.2 (3)
C6T—Ru—C4T	68.65 (18)	C2T—C3T—C4T	122.4 (4)
N7A—Ru—C4T	168.51 (16)	C2T—C3T—Ru	72.2 (3)
C2T—Ru—C4T	68.43 (19)	C4T—C3T—Ru	72.5 (3)
C1T—Ru—C4T	81.85 (18)	C5T—C4T—C3T	116.5 (4)
N1A—Ru—Cl1	87.70 (11)	C5T—C4T—C8T	124.1 (5)
C3T—Ru—Cl1	86.95 (14)	C3T—C4T—C8T	119.3 (4)
C5T—Ru—Cl1	122.81 (13)	C5T—C4T—Ru	70.0 (2)
C6T—Ru—Cl1	160.51 (14)	C3T—C4T—Ru	69.5 (3)
N7A—Ru—Cl1	90.75 (11)	C8T—C4T—Ru	129.4 (4)
C2T—Ru—Cl1	109.77 (13)	C4T—C5T—C6T	121.6 (4)
C1T—Ru—Cl1	146.73 (13)	C4T—C5T—Ru	72.7 (2)
C4T—Ru—Cl1	92.16 (12)	C6T—C5T—Ru	70.8 (3)
C2A—N1A—C5A	107.7 (3)	C1T—C6T—C5T	120.9 (4)
C2A—N1A—Ru	112.2 (3)	C1T—C6T—Ru	72.0 (3)
C5A—N1A—Ru	119.6 (3)	C5T—C6T—Ru	70.8 (2)
N1A—C2A—C6A	109.3 (4)	C4T—C8T—C9T	114.1 (5)
N1A—C2A—C3A	105.5 (4)	C4T—C8T—C10T	109.7 (5)
C6A—C2A—C3A	112.2 (4)	C9T—C8T—C10T	110.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···Cl2	0.91	2.40	3.273 (4)	161
N7A—H7A···Cl2^i	0.91	2.51	3.352 (4)	154

Symmetry code: (i) x−1/2, −y+1/2, −z.