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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008787/gg1008sup1.cif
Contains datablocks Ru(II)-pcym-anmethpyrrolidine, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008787/gg1008Isup2.hkl
Contains datablock I

CCDC reference: 150766

Computing details top

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) top
Crystal data top
[RuCl(C10H14)(C11H16N2)]ClDx = 1.560 Mg m3
Mr = 482.44Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 45 reflections
a = 8.2107 (3) Åθ = 12.5–18.2°
b = 9.3093 (4) ŵ = 1.03 mm1
c = 26.8707 (9) ÅT = 295 K
V = 2053.89 (13) Å3Brick-shaped, yellow
Z = 40.63 × 0.39 × 0.24 mm
F(000) = 992
Data collection top
STOE STADI4
diffractometer
6503 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 32.5°, θmin = 1.5°
ω scansh = 1212
Absorption correction: ψ scan
(X-RED; Stoe & Cie, 1996)
k = 014
Tmin = 0.466, Tmax = 0.781l = 040
8338 measured reflections3 standard reflections every 60 min
7328 independent reflections intensity decay: 5.7%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.142Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2) + (0.070P)2 + 3.P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
7328 reflectionsΔρmax = 1.14 e Å3
238 parametersΔρmin = 1.63 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: heavy-atom methodAbsolute structure parameter: 0.05 (5)
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.

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 (Å2) top
xyzUiso*/Ueq
Ru0.40413 (4)0.36500 (3)0.131187 (11)0.02365 (8)
Cl10.24482 (17)0.26862 (15)0.19947 (5)0.0390 (3)
Cl20.70591 (18)0.07195 (15)0.03569 (5)0.0418 (3)
N1A0.3716 (5)0.1629 (4)0.09410 (14)0.0286 (8)
H1A0.45740.15510.07280.034*
C2A0.2218 (6)0.1614 (4)0.06162 (17)0.0299 (9)
H2A0.25130.18800.02750.036*
C3A0.1598 (8)0.0073 (6)0.0630 (2)0.0407 (12)
H31A0.21460.05130.03830.049*
H32A0.04320.00310.05740.049*
C4A0.2026 (7)0.0407 (6)0.1158 (2)0.0404 (11)
H41A0.12430.00470.13970.048*
H42A0.20720.14460.11810.048*
C5A0.3725 (7)0.0251 (5)0.1242 (2)0.0372 (11)
H51A0.39010.04510.15920.045*
H52A0.45760.03910.11260.045*
C6A0.0988 (7)0.2666 (5)0.08200 (18)0.0318 (8)
H61A0.00830.27650.05900.038*
H62A0.05680.23270.11360.038*
N7A0.1819 (5)0.4079 (4)0.08864 (14)0.0284 (7)
H7A0.21790.43170.05770.034*
C1F0.0694 (5)0.5233 (5)0.10208 (17)0.0283 (8)
C2F0.0011 (7)0.6062 (5)0.0644 (2)0.0380 (11)
H2F0.02780.58830.03140.046*
C3F0.1056 (8)0.7169 (5)0.0763 (2)0.0447 (12)
H3F0.15110.77200.05100.054*
C4F0.1456 (7)0.7437 (6)0.1247 (3)0.0451 (13)
H4F0.21500.81940.13240.054*
C5F0.0811 (7)0.6598 (6)0.1623 (2)0.0448 (12)
H5F0.11260.67550.19510.054*
C6F0.0292 (7)0.5501 (6)0.1515 (2)0.0371 (10)
H6F0.07630.49660.17690.044*
C1T0.5178 (6)0.5560 (5)0.09787 (17)0.0305 (9)
C2T0.4798 (7)0.5857 (5)0.14851 (17)0.0325 (9)
H2T0.42000.66720.15660.039*
C3T0.5319 (6)0.4931 (5)0.18641 (17)0.0317 (9)
H3T0.50150.51250.21910.038*
C4T0.6289 (5)0.3688 (6)0.17668 (16)0.0295 (8)
C5T0.6678 (5)0.3416 (5)0.12656 (18)0.0306 (9)
H5T0.73130.26200.11880.037*
C6T0.6134 (6)0.4343 (5)0.08743 (17)0.0302 (9)
H6T0.64050.41280.05470.036*
C7T0.4578 (7)0.6513 (6)0.0568 (2)0.0417 (11)
H71T0.53390.72810.05150.050*
H72T0.35380.69050.06580.050*
H73T0.44700.59630.02670.050*
C8T0.6785 (7)0.2729 (7)0.2195 (2)0.0409 (11)
H8T0.58020.25120.23870.049*
C9T0.7535 (9)0.1306 (8)0.2035 (3)0.0570 (16)
H91T0.67970.08070.18190.068*
H92T0.77430.07310.23250.068*
H93T0.85400.14820.18630.068*
C10T0.7957 (9)0.3540 (9)0.2539 (2)0.0565 (16)
H01T0.81140.29990.28390.068*
H02T0.75070.44630.26190.068*
H03T0.89850.36640.23740.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru0.02573 (13)0.02137 (12)0.02384 (12)0.00113 (12)0.00172 (12)0.00144 (12)
Cl10.0409 (6)0.0417 (6)0.0343 (5)0.0026 (5)0.0094 (5)0.0061 (5)
Cl20.0480 (7)0.0422 (7)0.0351 (5)0.0082 (6)0.0019 (5)0.0051 (5)
N1A0.0303 (19)0.0234 (17)0.0319 (17)0.0008 (13)0.0006 (13)0.0018 (13)
C2A0.039 (2)0.0223 (19)0.0287 (18)0.0006 (16)0.0026 (17)0.0005 (14)
C3A0.051 (3)0.026 (2)0.045 (3)0.004 (2)0.008 (2)0.004 (2)
C4A0.046 (3)0.025 (2)0.050 (3)0.006 (2)0.005 (2)0.0036 (19)
C5A0.043 (3)0.0263 (19)0.042 (3)0.0003 (18)0.006 (2)0.0008 (18)
C6A0.030 (2)0.0254 (18)0.040 (2)0.0012 (19)0.005 (2)0.0056 (16)
N7A0.033 (2)0.0235 (16)0.0287 (17)0.0004 (14)0.0013 (14)0.0020 (13)
C1F0.025 (2)0.0239 (18)0.036 (2)0.0021 (15)0.0003 (16)0.0027 (15)
C2F0.037 (2)0.030 (2)0.047 (3)0.0021 (19)0.001 (2)0.0041 (19)
C3F0.038 (3)0.027 (2)0.070 (4)0.003 (2)0.002 (3)0.007 (2)
C4F0.031 (2)0.028 (2)0.076 (4)0.0027 (18)0.006 (3)0.008 (3)
C5F0.041 (3)0.040 (3)0.053 (3)0.000 (2)0.006 (2)0.018 (2)
C6F0.036 (3)0.037 (2)0.039 (2)0.002 (2)0.002 (2)0.005 (2)
C1T0.033 (2)0.026 (2)0.032 (2)0.0053 (17)0.0001 (17)0.0001 (16)
C2T0.039 (3)0.0250 (19)0.033 (2)0.0054 (18)0.0018 (18)0.0058 (17)
C3T0.037 (2)0.032 (2)0.0270 (19)0.0008 (19)0.0019 (17)0.0070 (17)
C4T0.0275 (19)0.031 (2)0.0294 (17)0.0003 (18)0.0032 (14)0.0022 (18)
C5T0.0244 (18)0.031 (2)0.037 (2)0.0026 (15)0.0008 (16)0.0047 (18)
C6T0.029 (2)0.031 (2)0.0310 (19)0.0010 (18)0.0086 (17)0.0011 (16)
C7T0.047 (3)0.035 (3)0.043 (3)0.007 (2)0.004 (2)0.010 (2)
C8T0.038 (3)0.046 (3)0.039 (2)0.002 (2)0.002 (2)0.008 (2)
C9T0.061 (4)0.044 (3)0.066 (4)0.009 (3)0.012 (3)0.009 (3)
C10T0.065 (4)0.067 (4)0.038 (3)0.008 (4)0.015 (3)0.004 (3)
Geometric parameters (Å, º) top
Ru—Cl12.4254 (12)C1F—C2F1.390 (7)
Ru—N1A2.146 (4)C1F—C6F1.390 (7)
Ru—N7A2.190 (4)C2F—C3F1.389 (7)
Ru—C1T2.199 (5)C3F—C4F1.364 (9)
Ru—C2T2.196 (5)C4F—C5F1.382 (9)
Ru—C3T2.174 (5)C5F—C6F1.395 (8)
Ru—C4T2.214 (4)C1T—C6T1.407 (7)
Ru—C5T2.179 (4)C1T—C2T1.423 (7)
Ru—C6T2.180 (5)C1T—C7T1.500 (7)
N1A—C2A1.508 (6)C2T—C3T1.401 (7)
N1A—C5A1.517 (6)C3T—C4T1.430 (7)
C2A—C6A1.510 (7)C4T—C5T1.407 (6)
C2A—C3A1.523 (7)C4T—C8T1.511 (7)
C3A—C4A1.527 (8)C5T—C6T1.432 (7)
C4A—C5A1.540 (8)C8T—C9T1.523 (9)
C6A—N7A1.493 (6)C8T—C10T1.533 (9)
N7A—C1F1.463 (6)
N1A—Ru—C3T149.11 (17)C2A—C3A—C4A102.8 (4)
N1A—Ru—C5T90.53 (16)C3A—C4A—C5A103.2 (5)
C3T—Ru—C5T67.32 (18)N1A—C5A—C4A104.7 (4)
N1A—Ru—C6T96.15 (16)N7A—C6A—C2A108.0 (4)
C3T—Ru—C6T79.95 (19)C1F—N7A—C6A112.8 (4)
C5T—Ru—C6T38.35 (18)C1F—N7A—Ru122.1 (3)
N1A—Ru—N7A79.26 (15)C6A—N7A—Ru106.4 (3)
C3T—Ru—N7A131.19 (17)C2F—C1F—C6F120.0 (4)
C5T—Ru—N7A144.69 (16)C2F—C1F—N7A118.9 (4)
C6T—Ru—N7A108.73 (16)C6F—C1F—N7A121.2 (4)
N1A—Ru—C2T162.52 (16)C3F—C2F—C1F120.0 (5)
C3T—Ru—C2T37.39 (18)C4F—C3F—C2F120.4 (5)
C5T—Ru—C2T79.90 (19)C3F—C4F—C5F120.1 (5)
C6T—Ru—C2T67.32 (19)C4F—C5F—C6F120.7 (5)
N7A—Ru—C2T100.13 (17)C1F—C6F—C5F118.9 (5)
N1A—Ru—C1T124.95 (16)C6T—C1T—C2T118.0 (4)
C3T—Ru—C1T68.24 (18)C6T—C1T—C7T120.8 (4)
C5T—Ru—C1T68.66 (18)C2T—C1T—C7T121.2 (5)
C6T—Ru—C1T37.48 (18)C6T—C1T—Ru70.5 (3)
N7A—Ru—C1T89.64 (17)C2T—C1T—Ru71.0 (3)
C2T—Ru—C1T37.78 (18)C7T—C1T—Ru129.7 (4)
N1A—Ru—C4T111.96 (17)C3T—C2T—C1T120.6 (5)
C3T—Ru—C4T38.01 (18)C3T—C2T—Ru70.4 (3)
C5T—Ru—C4T37.34 (16)C1T—C2T—Ru71.2 (3)
C6T—Ru—C4T68.65 (18)C2T—C3T—C4T122.4 (4)
N7A—Ru—C4T168.51 (16)C2T—C3T—Ru72.2 (3)
C2T—Ru—C4T68.43 (19)C4T—C3T—Ru72.5 (3)
C1T—Ru—C4T81.85 (18)C5T—C4T—C3T116.5 (4)
N1A—Ru—Cl187.70 (11)C5T—C4T—C8T124.1 (5)
C3T—Ru—Cl186.95 (14)C3T—C4T—C8T119.3 (4)
C5T—Ru—Cl1122.81 (13)C5T—C4T—Ru70.0 (2)
C6T—Ru—Cl1160.51 (14)C3T—C4T—Ru69.5 (3)
N7A—Ru—Cl190.75 (11)C8T—C4T—Ru129.4 (4)
C2T—Ru—Cl1109.77 (13)C4T—C5T—C6T121.6 (4)
C1T—Ru—Cl1146.73 (13)C4T—C5T—Ru72.7 (2)
C4T—Ru—Cl192.16 (12)C6T—C5T—Ru70.8 (3)
C2A—N1A—C5A107.7 (3)C1T—C6T—C5T120.9 (4)
C2A—N1A—Ru112.2 (3)C1T—C6T—Ru72.0 (3)
C5A—N1A—Ru119.6 (3)C5T—C6T—Ru70.8 (2)
N1A—C2A—C6A109.3 (4)C4T—C8T—C9T114.1 (5)
N1A—C2A—C3A105.5 (4)C4T—C8T—C10T109.7 (5)
C6A—C2A—C3A112.2 (4)C9T—C8T—C10T110.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···Cl20.912.403.273 (4)161
N7A—H7A···Cl2i0.912.513.352 (4)154
Symmetry code: (i) x1/2, y+1/2, z.
 

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