Literature DB >> 21200593

(η-Benzene)(2,2'-bipyridine-κN,N')chloridoruthenium(II) chloride methanol sesquisolvate.

Matthew I J Polson1.   

Abstract

In the title compound, [RuCl(C(6)H(6))(C(10)H(8)N(2))]Cl·1.5CH(4)O, the Ru(II) atom is in a distorted octa-hedral environment coordinated by an η(6)-benzene ring, a chelating 2,2'-bipyridine ligand and a chloride ion. The asymmetric unit is completed by a chloride anion and two methanol mol-ecules, one of which is disordered about a centre of inversion with an occupancy of 0.5. It is an example of a ruthenium complex with a less sterically congested environment than in similar derivatives. In the crystal structure, O-H⋯Cl hydrogen bonds, together with π-π stacking inter-actions [centroid-centroid distances of 3.472Å(2) Å], stabilize the structure.

Entities:  

Year:  2007        PMID： 21200593      PMCID： PMC2915169          DOI： 10.1107/S1600536807066858

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For literature concerning the synthesis of this class of compound, see Freedman et al. (2001 ▶). For related structures, see Himeda et al. (2007 ▶); Lalrempuia & Kollipara (2003 ▶).

Experimental

Crystal data

[RuCl(C6H6)(C10H8N2)]Cl·1.5CH4O M = 454.33 Triclinic, a = 6.9027 (11) Å b = 10.2346 (16) Å c = 12.895 (2) Å α = 85.597 (2)° β = 84.531 (2)° γ = 75.875 (2)° V = 878.1 (2) Å3 Z = 2 Mo Kα radiation μ = 1.21 mm−1 T = 93 (2) K 0.36 × 0.34 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.660, T max = 0.854 4385 measured reflections 3082 independent reflections 2867 reflections with I > 2σ(I) R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.086 S = 1.06 3082 reflections 220 parameters H-atom parameters constrained Δρmax = 1.13 e Å−3 Δρmin = −0.69 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066858/sj2425sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066858/sj2425Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[RuCl(C6H6)(C10H8N2)]Cl·1.5CH4OZ = 2
Mr = 454.33F000 = 458
Triclinic, P1Dx = 1.718 Mg m−3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 6.9027 (11) ÅCell parameters from 3474 reflections
b = 10.2346 (16) Åθ = 2.5–26.4º
c = 12.895 (2) ŵ = 1.21 mm−1
α = 85.597 (2)ºT = 93 (2) K
β = 84.531 (2)ºBlock, yellow
γ = 75.875 (2)º0.36 × 0.34 × 0.13 mm
V = 878.1 (2) Å3
Bruker APEXII CCD area-detector diffractometer3082 independent reflections
Radiation source: sealed tube2867 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.014
T = 93(2) Kθmax = 25.1º
φ and ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2007)h = −8→8
Tmin = 0.660, Tmax = 0.854k = −12→12
4385 measured reflectionsl = −15→10
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.086  w = 1/[σ2(Fo2) + (0.0562P)2 + 0.5007P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3082 reflectionsΔρmax = 1.13 e Å−3
220 parametersΔρmin = −0.69 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/UeqOcc. (<1)
Ru10.60854 (4)0.67682 (3)0.77268 (2)0.02474 (11)
Cl10.89451 (12)0.76724 (9)0.71514 (7)0.0277 (2)
Cl20.12633 (18)0.29047 (14)0.82005 (9)0.0536 (3)
N10.6736 (4)0.5821 (3)0.6319 (2)0.0217 (6)
N20.4510 (4)0.8207 (3)0.6686 (2)0.0244 (6)
C70.6008 (5)0.6559 (3)0.5465 (2)0.0201 (7)
C120.4677 (5)0.7878 (3)0.5677 (3)0.0217 (7)
C20.4713 (8)0.7559 (5)0.9230 (3)0.0530 (13)
H20.42720.85590.92890.064*
C10.3440 (7)0.6888 (5)0.8796 (3)0.0463 (11)
H10.21010.74070.85790.056*
C60.4177 (8)0.5533 (5)0.8541 (3)0.0499 (13)
H60.33750.50850.81400.060*
C30.6688 (8)0.6925 (6)0.9351 (3)0.0557 (14)
H30.76340.74780.94960.067*
C40.7456 (8)0.5604 (6)0.9086 (3)0.0515 (12)
H40.89390.52240.90470.062*
C50.6250 (8)0.4896 (5)0.8699 (3)0.0489 (12)
H50.68800.40120.83850.059*
C110.7918 (5)0.4575 (3)0.6204 (3)0.0234 (7)
H110.84300.40540.68030.028*
C80.6504 (5)0.6079 (3)0.4470 (2)0.0220 (7)
H80.60230.66280.38760.026*
C90.7708 (5)0.4794 (4)0.4354 (3)0.0232 (7)
H90.80480.44420.36820.028*
C100.8406 (5)0.4030 (4)0.5234 (3)0.0236 (7)
H100.92150.31400.51740.028*
C140.2393 (5)0.9964 (4)0.5210 (3)0.0307 (8)
H140.16551.05620.47080.037*
C130.3616 (5)0.8737 (4)0.4923 (3)0.0255 (7)
H130.37290.84850.42220.031*
C160.3322 (5)0.9412 (4)0.6948 (3)0.0307 (8)
H160.32160.96500.76520.037*
C150.2259 (5)1.0307 (4)0.6237 (3)0.0337 (9)
H150.14441.11500.64470.040*
O510.5683 (5)0.2257 (4)0.7539 (3)0.0553 (8)
H510.44590.23340.77160.083*
C500.6807 (7)0.1122 (5)0.8067 (4)0.0484 (11)
H50A0.59760.08370.86580.073*
H50B0.79730.13470.83220.073*
H50C0.72610.03880.75900.073*
O610.1958 (9)0.0351 (6)0.9544 (5)0.0413 (13)*0.50
H610.18720.10920.92010.062*0.50
C60−0.002 (4)0.035 (3)1.016 (2)0.135 (8)*0.50
H60A0.01490.03641.09090.202*0.50
H60B−0.0448−0.04591.00320.202*0.50
H60C−0.10280.11560.99500.202*0.50
U11U22U33U12U13U23
Ru10.02860 (18)0.03351 (18)0.01564 (16)−0.01396 (12)−0.00330 (11)−0.00015 (11)
Cl10.0235 (4)0.0287 (4)0.0335 (5)−0.0100 (3)−0.0057 (3)−0.0006 (3)
Cl20.0509 (7)0.0718 (8)0.0416 (6)−0.0182 (6)−0.0168 (5)0.0028 (5)
N10.0215 (14)0.0283 (15)0.0187 (13)−0.0131 (12)−0.0036 (11)0.0024 (11)
N20.0206 (14)0.0305 (16)0.0246 (15)−0.0109 (12)−0.0005 (11)−0.0024 (12)
C70.0175 (16)0.0258 (17)0.0203 (16)−0.0120 (13)−0.0044 (12)0.0032 (13)
C120.0176 (16)0.0281 (17)0.0231 (16)−0.0140 (14)−0.0012 (13)0.0022 (13)
C20.072 (3)0.064 (3)0.028 (2)−0.031 (3)0.017 (2)−0.015 (2)
C10.041 (2)0.076 (3)0.0229 (19)−0.021 (2)0.0037 (17)0.008 (2)
C60.073 (3)0.081 (3)0.0145 (18)−0.058 (3)−0.0018 (19)0.0070 (19)
C30.065 (3)0.099 (4)0.0178 (19)−0.046 (3)−0.0041 (19)−0.006 (2)
C40.054 (3)0.085 (4)0.0195 (19)−0.027 (3)−0.0085 (19)0.016 (2)
C50.074 (3)0.048 (3)0.022 (2)−0.020 (2)0.007 (2)0.0148 (18)
C110.0226 (17)0.0259 (17)0.0242 (17)−0.0112 (14)−0.0059 (13)0.0049 (13)
C80.0191 (16)0.0318 (18)0.0176 (16)−0.0122 (14)−0.0039 (12)0.0046 (13)
C90.0179 (16)0.0344 (19)0.0217 (16)−0.0140 (14)−0.0014 (13)−0.0033 (14)
C100.0167 (16)0.0267 (17)0.0298 (18)−0.0096 (14)−0.0039 (13)0.0007 (14)
C140.0183 (17)0.0299 (19)0.046 (2)−0.0122 (15)−0.0043 (15)0.0085 (16)
C130.0214 (17)0.0291 (18)0.0296 (18)−0.0138 (14)−0.0050 (14)0.0045 (14)
C160.0263 (19)0.036 (2)0.0326 (19)−0.0139 (16)0.0049 (15)−0.0091 (16)
C150.0213 (18)0.0283 (19)0.051 (2)−0.0086 (15)0.0045 (16)−0.0028 (17)
O510.063 (2)0.058 (2)0.0437 (18)−0.0138 (17)−0.0090 (16)0.0107 (15)
C500.048 (3)0.042 (2)0.054 (3)−0.010 (2)−0.012 (2)0.005 (2)
Ru1—N12.083 (3)C4—H41.0000
Ru1—N22.084 (3)C5—H51.0000
Ru1—C12.165 (4)C11—C101.387 (5)
Ru1—C62.186 (4)C11—H110.9500
Ru1—C52.193 (4)C8—C91.385 (5)
Ru1—C22.198 (4)C8—H80.9500
Ru1—C42.198 (4)C9—C101.384 (5)
Ru1—C32.199 (4)C9—H90.9500
Ru1—Cl12.4105 (9)C10—H100.9500
N1—C111.346 (4)C14—C151.385 (6)
N1—C71.352 (4)C14—C131.386 (5)
N2—C161.351 (5)C14—H140.9500
N2—C121.356 (4)C13—H130.9500
C7—C81.392 (5)C16—C151.374 (6)
C7—C121.464 (5)C16—H160.9500
C12—C131.394 (5)C15—H150.9500
C2—C31.378 (8)O51—C501.398 (6)
C2—C11.417 (7)O51—H510.8400
C2—H21.0000C50—H50A0.9800
C1—C61.408 (7)C50—H50B0.9800
C1—H11.0000C50—H50C0.9800
C6—C51.447 (7)O61—C601.51 (3)
C6—H61.0000O61—H610.8400
C3—C41.383 (8)C60—H60A0.9800
C3—H31.0000C60—H60B0.9800
C4—C51.378 (7)C60—H60C0.9800
N1—Ru1—N277.18 (11)C1—C6—Ru170.3 (2)
N1—Ru1—C1127.42 (15)C5—C6—Ru170.9 (2)
N2—Ru1—C191.75 (15)C1—C6—H6120.4
N1—Ru1—C699.21 (14)C5—C6—H6120.4
N2—Ru1—C6111.47 (16)Ru1—C6—H6120.4
C1—Ru1—C637.76 (19)C2—C3—C4120.9 (5)
N1—Ru1—C594.95 (14)C2—C3—Ru171.7 (2)
N2—Ru1—C5148.17 (16)C4—C3—Ru171.6 (2)
C1—Ru1—C568.40 (19)C2—C3—H3119.0
C6—Ru1—C538.58 (19)C4—C3—H3119.0
N1—Ru1—C2165.29 (15)Ru1—C3—H3119.0
N2—Ru1—C2101.06 (17)C5—C4—C3120.4 (5)
C1—Ru1—C237.89 (18)C5—C4—Ru171.5 (2)
C6—Ru1—C267.59 (18)C3—C4—Ru171.7 (3)
C5—Ru1—C278.80 (19)C5—C4—H4119.3
N1—Ru1—C4116.02 (17)C3—C4—H4119.3
N2—Ru1—C4166.80 (17)Ru1—C4—H4119.3
C1—Ru1—C480.20 (18)C4—C5—C6120.4 (5)
C6—Ru1—C468.00 (18)C4—C5—Ru171.9 (3)
C5—Ru1—C436.57 (19)C6—C5—Ru170.5 (2)
C2—Ru1—C466.2 (2)C4—C5—H5119.1
N1—Ru1—C3151.14 (18)C6—C5—H5119.1
N2—Ru1—C3130.37 (18)Ru1—C5—H5119.1
C1—Ru1—C367.60 (18)N1—C11—C10121.8 (3)
C6—Ru1—C379.73 (17)N1—C11—H11119.1
C5—Ru1—C366.1 (2)C10—C11—H11119.1
C2—Ru1—C336.5 (2)C9—C8—C7119.3 (3)
C4—Ru1—C336.7 (2)C9—C8—H8120.4
N1—Ru1—Cl184.01 (8)C7—C8—H8120.4
N2—Ru1—Cl186.34 (8)C10—C9—C8118.8 (3)
C1—Ru1—Cl1147.23 (14)C10—C9—H9120.6
C6—Ru1—Cl1162.19 (14)C8—C9—H9120.6
C5—Ru1—Cl1123.93 (14)C9—C10—C11119.6 (3)
C2—Ru1—Cl1110.55 (13)C9—C10—H10120.2
C4—Ru1—Cl194.76 (13)C11—C10—H10120.2
C3—Ru1—Cl189.00 (13)C15—C14—C13119.2 (3)
C11—N1—C7119.0 (3)C15—C14—H14120.4
C11—N1—Ru1124.3 (2)C13—C14—H14120.4
C7—N1—Ru1116.5 (2)C14—C13—C12119.1 (3)
C16—N2—C12118.5 (3)C14—C13—H13120.4
C16—N2—Ru1125.0 (2)C12—C13—H13120.4
C12—N2—Ru1116.5 (2)N2—C16—C15122.7 (3)
N1—C7—C8121.6 (3)N2—C16—H16118.6
N1—C7—C12114.8 (3)C15—C16—H16118.6
C8—C7—C12123.6 (3)C16—C15—C14119.0 (3)
N2—C12—C13121.4 (3)C16—C15—H15120.5
N2—C12—C7114.6 (3)C14—C15—H15120.5
C13—C12—C7124.0 (3)C50—O51—H51109.5
C3—C2—C1120.7 (5)O51—C50—H50A109.5
C3—C2—Ru171.8 (3)O51—C50—H50B109.5
C1—C2—Ru169.8 (2)H50A—C50—H50B109.5
C3—C2—H2118.9O51—C50—H50C109.5
C1—C2—H2118.9H50A—C50—H50C109.5
Ru1—C2—H2118.9H50B—C50—H50C109.5
C6—C1—C2119.4 (5)C60—O61—H61109.5
C6—C1—Ru171.9 (2)O61—C60—H60A109.5
C2—C1—Ru172.3 (2)O61—C60—H60B109.5
C6—C1—H1120.0H60A—C60—H60B109.5
C2—C1—H1120.0O61—C60—H60C109.5
Ru1—C1—H1120.0H60A—C60—H60C109.5
C1—C6—C5118.2 (4)H60B—C60—H60C109.5
D—H···AD—HH···AD···AD—H···A
O51—H51···Cl20.842.183.013 (4)170
O61—H61···Cl20.842.152.986 (6)171
Ru1—N12.083 (3)
Ru1—N22.084 (3)
Ru1—C12.165 (4)
Ru1—C62.186 (4)
Ru1—C52.193 (4)
Ru1—C22.198 (4)
Ru1—C42.198 (4)
Ru1—C32.199 (4)
Ru1—Cl12.4105 (9)
N1—Ru1—N277.18 (11)
N1—Ru1—Cl184.01 (8)
N2—Ru1—Cl186.34 (8)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O51—H51⋯Cl20.842.183.013 (4)170
O61—H61⋯Cl20.842.152.986 (6)171
  1 in total

1.  Convenient synthesis of tris-heteroleptic ruthenium(II) polypyridyl complexes.

Authors:  D A Freedman; J K Evju; M K Pomije; K R Mann
Journal:  Inorg Chem       Date:  2001-10-22       Impact factor: 5.165
  1 in total

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