[mer,trans-(NN′N)RuCl2(NC5H5)]·C7H8 {NN′N = 2,6-bis-[(di­methyl­amino)­methyl]­pyridine}

Back, S.; Rheinwald, G.; Río, I. del; Koten, G. van; Lang, H.

doi:10.1107/S1600536801014878

[mer,trans-(NN'N)RuCl₂(NC₅H₅)]·C₇H₈ {NN'N = 2,6-bis-[(dimethylamino)methyl]pyridine}

S. Back, G. Rheinwald, I. del Río, G. van Koten and H. Lang

The title compound, mer,trans-{2,6-bis[(dimethylamino)methyl]pyridine}dichloropyridineruthenium(II) toluene solvate, [RuCl₂(C₁₁H₁₉N₃)(C₅H₅N)]·C₇H₈, has metal-ligand dimensions of Ru-N_py(NN'N) 1.962 (2) Å, Ru-N(NN'N) 2.348 (3) Å, Ru-N(NN'N) 2.251 (3) Å, Ru-N_py 2.096 (2) Å and Ru-Cl 2.3502 (7) or 2.3581 (7) Å (py = pyridine, C₅H₅N). Angles are N_py-Ru-N(NN'N) 178.37 (9)°, (NN'N)N-Ru-N(NN'N) 160.57 (9)° and Cl-Ru-Cl 177.19 (3)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801014878/na6084sup1.cif Contains datablocks global, II
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801014878/na6084IIsup2.hkl Contains datablock II

CCDC reference: 118726

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R factor = 0.052
wR factor = 0.117
Data-to-parameter ratio = 23.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           38.62
         From the CIF: _reflns_number_total               9359
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns        13764
         Completeness (_total/calc)             68.00%
          Alert A: < 85% complete (theta max?)

PLAT_706  Alert A H...A   Calc     3.07(5), Rep     2.68(4), Dev.      7.80 Sigma
                     H10C -CL1     1.555   1.555

PLAT_706  Alert A H...A   Calc    27.65(4), Rep     2.73(5), Dev.    623.00 Sigma
                     H4   -CL1     1.555   6.555

PLAT_706  Alert A H...A   Calc    19.95(4), Rep     2.65(4), Dev.    432.50 Sigma
                     H14  -CL2     1.555   3.455

PLAT_707  Alert A D...A   Calc   27.139(3), Rep    3.522(3), Dev.   7872.33 Sigma
                     C4   -CL1     1.555   6.555

PLAT_707  Alert A D...A   Calc   19.619(4), Rep    3.606(4), Dev.   4003.25 Sigma
                     C14  -CL2     1.555   3.455

PLAT_708  Alert A D-H..A  Calc       81(3), Rep      104(3), Dev.      7.67 Sigma
                     C10  -H10C -CL1     1.555   1.555   1.555

PLAT_708  Alert A D-H..A  Calc       52(3), Rep      158(4), Dev.     35.33 Sigma
                     C4   -H4   -CL1     1.555   1.555   6.555

PLAT_708  Alert A D-H..A  Calc       69(2), Rep      170(3), Dev.     50.50 Sigma
                     C14  -H14  -CL2     1.555   1.555   3.455


 Alert Level B:



CRYSS_02  Alert B The value of _exptl_crystal_size_min is > 0.6
 Minimum crystal size given =   0.900

CRYSS_02  Alert B The value of _exptl_crystal_size_mid is > 0.8
 Mid crystal size given     =   1.200

CRYSS_02  Alert B The value of _exptl_crystal_size_max is > 1.0
 Maximum crystal size given =   1.200


 Alert Level C:



PLAT_362  Alert C Short  C(sp3)-C(sp2) Bond  C(1)   -   C(6)   =       1.39 Ang.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      1
                   N4  -RU1 -N1  -C5     97.00  4.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      6
                   N4  -RU1 -N1  -C1    -79.00  4.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     41
                   N1  -RU1 -N4  -C12   135.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     46
                   N1  -RU1 -N4  -C16   -42.00  4.00   1.555   1.555   1.555   1.555

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           38.62
         From the CIF: _reflns_number_total               9359
         From the CIF: _diffrn_reflns_limit_ max hkl   20.   20.   43.
         From the CIF: _diffrn_reflns_limit_ min hkl  -10.  -13.  -10.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl   22.   24.   47.
         Calculated minimum hkl  -22.  -24.  -47.
          ALERT: Expected hkl max differ from CIF values


 9 Alert Level A = Potentially serious problem

 3 Alert Level B = Potential problem

 5 Alert Level C = Please check

Comment top

Recently, interest has been focused on the chemistry of bis-orthochelating aromatic ligands (Rietveld et al., 1997). This was due to their applicability to catalytic processes (Abbenhuis, del Río et al., 1998) or materials science (Steenwinkel et al., 1998). In this context, the dinitrogen-bridged bis-ruthenium complex {Ru}N≡N{Ru}, (I) [{Ru} = mer,trans-(C₅H₃N(CH₂NMe₂)₂-2,6)-RuCl₂] (Abbenhuis, Boersma & van Koten, 1998), has been studied in the synthesis of bioactive arylpiperazines. In order to gain a deeper insight into the catalytic behaviour of (I), this homodinuclear complex was reacted with various N-donor molecules (del R\'io et al., 2000). Treatment of (I) with two equivalents of py (py = pyridine, C₅H₅N) leads to the formation of the title compound {Ru}py·C₇H₈, (II), in high yield by loss of N₂. We report here on the structure of the (II), which incorporates two structural type pyridine ligands, i.e. C₅H₅N and C₅H₃N(CH₂NMe₂)₂-2,6.

The X-ray diffraction study confirms the general structure of (II) in solution, suggested on the basis of the NMR (¹H, ¹³C{¹H}) and IR data of (II) (Fig. 1).

In (II), the Ru^II centre occupies a distorted octahedral environment, with the three N-donor atoms of the NN'N-ligand in a meridional position. The Cl atoms are forced in the apical positions and are trans-orientated to each other. In general, the Ru—N_py, Ru—N_NMe and Ru—Cl distances Ru1—Cl1 [2.3502 (7) Å], Ru1—Cl2 [2.3581 (7) Å], Ru1—N1 [1.962 (2) Å], Ru1—N2 [2.348 (3) Å] and Ru1—N3 [2.251 (3) Å], as well as the angles around the Ru^II centre Cl1—Ru1—Cl2 [177.19 (3)] and N2—Ru1—N3 [160.57 (9)°] of the {Ru} building block are consistent with those values reported for this type of complex fragment (del Rio et al., 2000). The length of the Ru1—N4 bond of 2.096 (2) Å is elongated when compared to the Ru1—N1 bond, but lies in the range of distances reported for other Ru^II–pyridine complexes, e.g. [Ru(py)₆]²⁺ with 2.10–2.14 Å (Templeton, 1979). Similar Ru—N_py distances are, e.g., found in [RuCl(py)₄(pz)]⁺ with 2.105 (4) Å (Coe et al., 1995). This relatively short Ru1—N1 distance can best be explained by the imbedding of the Ru^II centre into the framework of the bis-orthochelating NN'N ligand. The angle N1—Ru1—N4 [178.37 (9)°] resembles the linearity of this array. The planes of the two pyridine ligands are tilted by 54.33 (10)°.

Experimental top

A solution of {Ru}N≡N{Ru}, (I) (128 mg, 0.2 mmol), and py (32 mg, 0.4 mmol) in THF (30 ml) was stirred for 1 h at 298 K. During the course of the reaction, the colour of the solution turned from brown to red and the turbidity disappeared. The reaction mixture was then concentrated to 5 ml and n-pentane (50 ml) was added. The supernatant liquid was carefully decanted and the residue was dried in vacuo to yield (II) [150 mg, 95% yield based on (I)] as a red–brown solid. By diffusion of n-pentane into a dichlormethane/n-pentane solution of (II), which has been endowed with toluene, at 298 K, single crystals of (II) could be obtained. M.p.: [K] 302 (decomposition). ¹H NMR (CDCl₃, p.p.m.): [δ] 2.38 (s, 12 H, NMe₂), 4.03 (s, 4H, CH₂), 7.1–7.2 (m, 2H, C₆H₃), 7.3–7.4 (m, 3 H, C₅H₅N), 7.7–7.8 (m, 1H, C₅H₃N), 9.6–9.7 (m, 2H, C₅H₅N). ¹³C{¹H} NMR (CDCl₃, p.p.m.): [δ] 53.6 (NMe₂), 72.1 (CH₂), 118.6 (CH/C₅H₃N), 123.5 (CH/C₅H₅N), 130.4 (i-C/C₅H₃N), 133.6 (CH/C₅H₅N), 156.4 (CH/C₅H₅N), 163.2 (CH/C₅H₃N). Analysis calculated for C₁₆H₂₄Cl₂N₄Ru (440.40): C 43.24, H 5.44, N 12.61%; found: C 43.79, H 5.78, N 12.23%.

Structure description top

The X-ray diffraction study confirms the general structure of (II) in solution, suggested on the basis of the NMR (¹H, ¹³C{¹H}) and IR data of (II) (Fig. 1).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai & Huttner, 1994); software used to prepare material for publication: SHELX97.

Figures top

Fig. 1. ZORTEP plot (50% probability) of complex (II) with molecular geometry and atom-numbering scheme (the toluene solvate molecule is not shown for clarity).

mer,trans-{2,6-bis[(dimethylamino)methyl]pyridine}dichloropyridineruthenium(II) toluene solvate top

Crystal data top

[RuCl₂(C₁₁H₁₉N₃)(C₅H₅N)]·C₇H₈	D_x = 1.470 Mg m⁻³
M_r = 536.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 31497 reflections
a = 12.7109 (1) Å	θ = 1.5–38.6°
b = 14.1115 (2) Å	µ = 0.88 mm⁻¹
c = 27.0317 (3) Å	T = 173 K
V = 4848.67 (10) Å³	Block, dark red
Z = 8	1.20 × 1.20 × 0.90 mm
F(000) = 2208

Data collection top

Bruker SMART CCD diffractometer	9359 independent reflections
Radiation source: fine-focus sealed tube	7687 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 38.6°, θ_min = 1.5°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 2000)	h = −10→20
T_min = 0.374, T_max = 0.451	k = −13→20
43809 measured reflections	l = −10→43

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0208P)² + 13.1818P] where P = (F_o² + 2F_c²)/3
S = 1.19	(Δ/σ)_max = 0.015
9359 reflections	Δρ_max = 2.07 e Å⁻³
400 parameters	Δρ_min = −1.86 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00058 (9)

Crystal data top

[RuCl₂(C₁₁H₁₉N₃)(C₅H₅N)]·C₇H₈	V = 4848.67 (10) Å³
M_r = 536.50	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.7109 (1) Å	µ = 0.88 mm⁻¹
b = 14.1115 (2) Å	T = 173 K
c = 27.0317 (3) Å	1.20 × 1.20 × 0.90 mm

Data collection top

Bruker SMART CCD diffractometer	9359 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 2000)	7687 reflections with I > 2σ(I)
T_min = 0.374, T_max = 0.451	R_int = 0.041
43809 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0208P)² + 13.1818P] where P = (F_o² + 2F_c²)/3
9359 reflections	Δρ_max = 2.07 e Å⁻³
400 parameters	Δρ_min = −1.86 e Å⁻³

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.

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
Ru1	0.025486 (15)	0.384516 (16)	0.129116 (7)	0.01901 (6)
Cl1	−0.08681 (5)	0.33484 (6)	0.19313 (2)	0.02838 (14)
Cl2	0.13228 (6)	0.43118 (6)	0.06208 (3)	0.03079 (15)
N1	0.10360 (17)	0.45844 (18)	0.17839 (8)	0.0222 (4)
N2	−0.04352 (18)	0.53882 (19)	0.12952 (9)	0.0248 (4)
N3	0.12600 (19)	0.2586 (2)	0.14864 (9)	0.0267 (5)
N4	−0.06081 (18)	0.30413 (19)	0.07806 (8)	0.0238 (4)
C1	0.0713 (2)	0.5483 (2)	0.19879 (10)	0.0263 (5)
C2	0.1231 (3)	0.6000 (3)	0.23496 (11)	0.0341 (7)
H2	0.102 (3)	0.660 (3)	0.2475 (14)	0.028 (9)*
C3	0.2067 (3)	0.5551 (3)	0.25109 (12)	0.0402 (8)
H3	0.240 (3)	0.586 (3)	0.2770 (14)	0.041 (11)*
C4	0.2387 (2)	0.4618 (3)	0.23040 (11)	0.0356 (7)
H4	0.292 (4)	0.433 (3)	0.2413 (16)	0.044 (12)*
C5	0.1861 (2)	0.4154 (2)	0.19298 (10)	0.0280 (6)
C6	−0.0259 (2)	0.5780 (2)	0.18130 (11)	0.0284 (5)
H6A	−0.034 (3)	0.654 (3)	0.1820 (13)	0.030 (10)*
H6B	−0.073 (4)	0.542 (3)	0.2048 (16)	0.046 (12)*
C7	0.0005 (3)	0.6164 (3)	0.09532 (14)	0.0353 (7)
H7A	−0.010 (3)	0.593 (3)	0.0604 (17)	0.045 (12)*
H7B	0.069 (4)	0.618 (3)	0.1014 (16)	0.044 (12)*
H7C	−0.030 (3)	0.683 (3)	0.0998 (15)	0.042 (12)*
C8	−0.1476 (3)	0.5401 (3)	0.12053 (14)	0.0361 (7)
H8A	−0.153 (3)	0.524 (3)	0.0851 (15)	0.038 (11)*
H8B	−0.178 (4)	0.493 (4)	0.1420 (16)	0.046 (12)*
H8C	−0.173 (3)	0.613 (3)	0.1274 (14)	0.038 (11)*
C9	0.2127 (2)	0.3193 (3)	0.16368 (12)	0.0315 (6)
H9A	0.242 (3)	0.344 (3)	0.1336 (13)	0.034 (10)*
H9B	0.253 (3)	0.273 (3)	0.1820 (13)	0.029 (9)*
C10	0.0960 (3)	0.1941 (3)	0.19153 (12)	0.0326 (6)
H10A	0.085 (3)	0.237 (3)	0.2192 (13)	0.028 (9)*
H10B	0.145 (3)	0.137 (3)	0.2005 (14)	0.035 (10)*
H10C	0.042 (4)	0.152 (3)	0.1840 (15)	0.043 (12)*
C11	0.1532 (3)	0.1858 (3)	0.10808 (13)	0.0346 (7)
H11A	0.202 (4)	0.141 (4)	0.1183 (17)	0.059 (15)*
H11B	0.104 (3)	0.141 (3)	0.1001 (15)	0.038 (11)*
H11C	0.172 (3)	0.229 (3)	0.0792 (13)	0.025 (9)*
C12	−0.0862 (2)	0.3479 (3)	0.03433 (10)	0.0294 (6)
H12	−0.063 (3)	0.419 (3)	0.0269 (13)	0.026 (9)*
C13	−0.1474 (3)	0.2998 (3)	0.00140 (11)	0.0380 (8)
H13	−0.165 (3)	0.332 (3)	−0.0289 (15)	0.042 (12)*
C14	−0.1821 (3)	0.2006 (3)	0.01172 (12)	0.0388 (8)
H14	−0.224 (3)	0.163 (3)	−0.0108 (15)	0.041 (11)*
C15	−0.1552 (2)	0.1540 (3)	0.05585 (12)	0.0327 (6)
H15	−0.172 (3)	0.087 (3)	0.0663 (13)	0.029 (9)*
C16	−0.0964 (2)	0.2084 (2)	0.08794 (11)	0.0279 (6)
H16	−0.082 (3)	0.178 (3)	0.1168 (13)	0.026 (9)*
C17	−0.0734 (3)	0.8834 (3)	0.07210 (11)	0.0322 (6)
C18	0.0140 (3)	0.9106 (3)	0.09256 (14)	0.0392 (7)
H18	0.065 (4)	0.928 (4)	0.0704 (16)	0.050 (13)*
C19	0.0257 (3)	0.9142 (3)	0.14351 (17)	0.0482 (10)
H19	0.081 (4)	0.933 (4)	0.1562 (16)	0.047 (13)*
C20	−0.0489 (3)	0.8921 (3)	0.17501 (14)	0.0431 (8)
H20	−0.039 (4)	0.893 (4)	0.208 (2)	0.067 (16)*
C21	−0.1364 (3)	0.8664 (3)	0.15506 (14)	0.0425 (8)
H21	−0.188 (4)	0.852 (3)	0.1765 (15)	0.043 (12)*
C22	−0.1482 (3)	0.8620 (3)	0.10411 (13)	0.0357 (7)
H22	−0.205 (4)	0.838 (4)	0.0889 (16)	0.050 (13)*
C23	−0.0860 (4)	0.8734 (4)	0.01697 (14)	0.0479 (10)
H23A	−0.034 (5)	0.907 (4)	−0.002 (2)	0.071 (17)*
H23B	−0.089 (4)	0.801 (4)	0.0086 (18)	0.062 (15)*
H23C	−0.130 (5)	0.914 (5)	0.007 (2)	0.08 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.01597 (9)	0.02393 (10)	0.01713 (8)	0.00102 (7)	0.00060 (6)	0.00107 (7)
Cl1	0.0239 (3)	0.0370 (4)	0.0242 (3)	0.0019 (3)	0.0070 (2)	0.0049 (2)
Cl2	0.0253 (3)	0.0383 (4)	0.0287 (3)	0.0013 (3)	0.0101 (2)	0.0042 (3)
N1	0.0162 (9)	0.0314 (12)	0.0188 (8)	0.0006 (8)	−0.0014 (7)	0.0005 (8)
N2	0.0179 (10)	0.0305 (12)	0.0260 (10)	0.0042 (8)	0.0014 (8)	0.0035 (9)
N3	0.0178 (10)	0.0336 (13)	0.0289 (11)	0.0046 (9)	0.0007 (8)	0.0014 (9)
N4	0.0189 (10)	0.0337 (13)	0.0189 (9)	0.0002 (9)	−0.0021 (7)	0.0015 (8)
C1	0.0214 (12)	0.0330 (15)	0.0246 (11)	−0.0020 (10)	0.0048 (9)	−0.0037 (10)
C2	0.0315 (15)	0.0439 (19)	0.0270 (12)	−0.0107 (13)	0.0062 (11)	−0.0103 (12)
C3	0.0285 (15)	0.068 (3)	0.0246 (12)	−0.0177 (15)	−0.0006 (11)	−0.0020 (15)
C4	0.0202 (13)	0.059 (2)	0.0281 (13)	−0.0074 (13)	−0.0063 (10)	0.0092 (13)
C5	0.0172 (12)	0.0424 (17)	0.0244 (11)	−0.0029 (10)	−0.0015 (9)	0.0062 (11)
C6	0.0236 (13)	0.0311 (15)	0.0307 (13)	0.0044 (11)	0.0041 (10)	−0.0044 (11)
C7	0.0330 (16)	0.0325 (17)	0.0403 (16)	0.0057 (13)	0.0073 (12)	0.0131 (14)
C8	0.0223 (14)	0.046 (2)	0.0403 (17)	0.0089 (13)	−0.0020 (11)	0.0017 (14)
C9	0.0178 (12)	0.0397 (18)	0.0370 (15)	0.0060 (11)	−0.0012 (10)	0.0042 (13)
C10	0.0274 (15)	0.0357 (17)	0.0346 (14)	0.0042 (12)	−0.0006 (11)	0.0111 (13)
C11	0.0312 (16)	0.0331 (17)	0.0394 (16)	0.0072 (13)	0.0054 (12)	−0.0056 (13)
C12	0.0216 (12)	0.0440 (18)	0.0227 (11)	−0.0036 (12)	−0.0010 (9)	0.0031 (11)
C13	0.0250 (14)	0.067 (3)	0.0219 (12)	−0.0036 (14)	−0.0037 (10)	−0.0009 (14)
C14	0.0205 (14)	0.062 (2)	0.0341 (15)	−0.0043 (14)	−0.0022 (11)	−0.0149 (15)
C15	0.0227 (13)	0.0381 (18)	0.0374 (15)	−0.0062 (12)	0.0031 (11)	−0.0075 (13)
C16	0.0202 (12)	0.0369 (16)	0.0267 (12)	−0.0009 (11)	0.0011 (9)	0.0004 (11)
C17	0.0316 (15)	0.0330 (16)	0.0320 (13)	0.0038 (12)	0.0006 (11)	0.0013 (12)
C18	0.0361 (18)	0.0371 (18)	0.0443 (18)	−0.0020 (14)	0.0015 (14)	−0.0028 (14)
C19	0.035 (2)	0.053 (2)	0.057 (2)	0.0045 (17)	−0.0133 (17)	−0.0125 (19)
C20	0.050 (2)	0.044 (2)	0.0354 (16)	0.0105 (17)	−0.0055 (15)	−0.0091 (15)
C21	0.0395 (19)	0.051 (2)	0.0373 (16)	0.0071 (16)	0.0087 (14)	−0.0044 (15)
C22	0.0299 (16)	0.0398 (19)	0.0373 (15)	0.0056 (13)	0.0019 (12)	−0.0034 (13)
C23	0.048 (2)	0.062 (3)	0.0334 (16)	0.004 (2)	0.0003 (15)	0.0008 (17)

Geometric parameters (Å, º) top

Ru1—Cl1	2.3501 (7)	C9—H9A	0.96 (4)
Ru1—Cl2	2.3580 (7)	C9—H9B	0.97 (4)
Ru1—N1	1.962 (2)	C10—H10A	0.98 (4)
Ru1—N2	2.348 (3)	C10—H10B	1.04 (4)
Ru1—N3	2.251 (3)	C10—H10C	0.93 (5)
Ru1—N4	2.096 (2)	C11—H11A	0.93 (6)
N1—C5	1.274 (4)	C11—H11B	0.91 (5)
N1—C1	1.442 (4)	C11—H11C	1.02 (4)
N2—C8	1.345 (4)	C12—C13	1.363 (4)
N2—C6	1.521 (4)	C12—H12	1.06 (4)
N2—C7	1.538 (4)	C13—C14	1.495 (6)
N3—C9	1.453 (4)	C13—H13	0.96 (4)
N3—C10	1.522 (4)	C14—C15	1.404 (5)
N3—C11	1.542 (4)	C14—H14	0.97 (4)
N4—C12	1.373 (4)	C15—C16	1.379 (4)
N4—C16	1.449 (4)	C15—H15	1.01 (4)
C1—C2	1.386 (4)	C16—H16	0.91 (4)
C1—C6	1.388 (4)	C17—C18	1.298 (5)
C2—C3	1.312 (5)	C17—C22	1.321 (5)
C2—H2	0.95 (4)	C17—C23	1.505 (5)
C3—C4	1.487 (6)	C18—C19	1.386 (6)
C3—H3	0.93 (4)	C18—H18	0.91 (5)
C4—C5	1.378 (4)	C19—C20	1.312 (6)
C4—H4	0.85 (5)	C19—H19	0.82 (5)
C5—C9	1.607 (5)	C20—C21	1.287 (6)
C6—H6A	1.08 (4)	C20—H20	0.90 (5)
C6—H6B	1.01 (5)	C21—C22	1.387 (5)
C7—H7A	1.01 (5)	C21—H21	0.90 (4)
C7—H7B	0.89 (5)	C22—H22	0.90 (5)
C7—H7C	1.02 (5)	C23—H23A	0.96 (6)
C8—H8A	0.99 (4)	C23—H23B	1.05 (6)
C8—H8B	0.96 (5)	C23—H23C	0.85 (7)
C8—H8C	1.10 (5)

Cl1—Ru1—Cl2	177.19 (3)	H8A—C8—H8B	114 (4)
Cl1—Ru1—N4	90.31 (7)	N2—C8—H8C	106 (2)
Cl2—Ru1—N4	86.93 (7)	H8A—C8—H8C	111 (3)
N1—Ru1—N2	72.10 (9)	H8B—C8—H8C	115 (3)
N1—Ru1—N3	88.47 (10)	N3—C9—C5	118.4 (2)
N2—Ru1—N3	160.57 (9)	N3—C9—H9A	106 (2)
N1—Ru1—N4	178.38 (9)	C5—C9—H9A	101 (3)
N4—Ru1—N3	91.39 (10)	N3—C9—H9B	99 (2)
N4—Ru1—N2	108.03 (9)	C5—C9—H9B	115 (2)
N1—Ru1—Cl1	88.06 (7)	H9A—C9—H9B	118 (3)
N3—Ru1—Cl1	86.37 (7)	N3—C10—H10A	104 (2)
N2—Ru1—Cl1	92.65 (6)	N3—C10—H10B	119 (2)
N1—Ru1—Cl2	94.70 (7)	H10A—C10—H10B	113 (3)
N3—Ru1—Cl2	94.24 (7)	N3—C10—H10C	113 (3)
N2—Ru1—Cl2	87.69 (6)	H10A—C10—H10C	117 (3)
C5—N1—C1	122.3 (3)	H10B—C10—H10C	90 (4)
C5—N1—Ru1	111.9 (2)	N3—C11—H11A	113 (3)
C1—N1—Ru1	125.66 (18)	N3—C11—H11B	118 (3)
C8—N2—C6	107.8 (2)	H11A—C11—H11B	93 (4)
C8—N2—C7	103.9 (3)	N3—C11—H11C	101 (2)
C6—N2—C7	103.9 (3)	H11A—C11—H11C	119 (4)
C8—N2—Ru1	112.3 (2)	H11B—C11—H11C	113 (3)
C6—N2—Ru1	106.65 (17)	C13—C12—N4	118.2 (3)
C7—N2—Ru1	121.41 (19)	C13—C12—H12	120.4 (19)
C9—N3—C10	109.2 (2)	N4—C12—H12	121.4 (19)
C9—N3—C11	114.9 (2)	C12—C13—C14	120.9 (3)
C10—N3—C11	101.5 (3)	C12—C13—H13	117 (3)
C9—N3—Ru1	91.76 (19)	C14—C13—H13	122 (3)
C10—N3—Ru1	120.52 (18)	C15—C14—C13	121.7 (3)
C11—N3—Ru1	119.13 (19)	C15—C14—H14	114 (3)
C12—N4—C16	120.3 (2)	C13—C14—H14	124 (3)
C12—N4—Ru1	116.5 (2)	C16—C15—C14	113.9 (3)
C16—N4—Ru1	123.11 (17)	C16—C15—H15	117 (2)
C2—C1—C6	120.3 (3)	C14—C15—H15	129 (2)
C2—C1—N1	126.7 (3)	C15—C16—N4	124.9 (3)
C6—C1—N1	112.9 (3)	C15—C16—H16	112 (2)
C3—C2—C1	111.4 (3)	N4—C16—H16	123 (2)
C3—C2—H2	123 (2)	C18—C17—C22	113.8 (3)
C1—C2—H2	126 (2)	C18—C17—C23	122.7 (4)
C2—C3—C4	121.6 (3)	C22—C17—C23	123.4 (4)
C2—C3—H3	113 (3)	C17—C18—C19	121.7 (4)
C4—C3—H3	125 (3)	C17—C18—H18	114 (3)
C5—C4—C3	124.4 (3)	C19—C18—H18	124 (3)
C5—C4—H4	114 (3)	C20—C19—C18	124.0 (4)
C3—C4—H4	121 (3)	C20—C19—H19	115 (3)
N1—C5—C4	113.6 (3)	C18—C19—H19	121 (3)
N1—C5—C9	115.0 (3)	C21—C20—C19	114.8 (4)
C4—C5—C9	131.4 (3)	C21—C20—H20	123 (3)
C1—C6—N2	109.5 (2)	C19—C20—H20	122 (3)
C1—C6—H6A	112 (2)	C20—C21—C22	121.5 (4)
N2—C6—H6A	111 (2)	C20—C21—H21	115 (3)
C1—C6—H6B	99 (3)	C22—C21—H21	123 (3)
N2—C6—H6B	108 (3)	C17—C22—C21	124.2 (4)
H6A—C6—H6B	115 (3)	C17—C22—H22	112 (3)
N2—C7—H7A	106 (3)	C21—C22—H22	124 (3)
N2—C7—H7B	105 (3)	C17—C23—H23A	114 (3)
H7A—C7—H7B	108 (4)	C17—C23—H23B	108 (3)
N2—C7—H7C	116 (2)	H23A—C23—H23B	113 (4)
H7A—C7—H7C	111 (3)	C17—C23—H23C	110 (4)
H7B—C7—H7C	109 (4)	H23A—C23—H23C	87 (5)
N2—C8—H8A	104 (2)	H23B—C23—H23C	124 (5)
N2—C8—H8B	106 (3)

N4—Ru1—N1—C5	97 (4)	N1—Ru1—N4—C16	−42 (4)
N3—Ru1—N1—C5	12.4 (2)	N3—Ru1—N4—C16	42.7 (2)
N2—Ru1—N1—C5	−167.8 (2)	N2—Ru1—N4—C16	−136.5 (2)
Cl1—Ru1—N1—C5	98.82 (19)	Cl1—Ru1—N4—C16	−43.6 (2)
Cl2—Ru1—N1—C5	−81.73 (19)	Cl2—Ru1—N4—C16	136.9 (2)
N4—Ru1—N1—C1	−79 (4)	C5—N1—C1—C2	1.1 (4)
N3—Ru1—N1—C1	−164.1 (2)	Ru1—N1—C1—C2	177.3 (2)
N2—Ru1—N1—C1	15.7 (2)	C5—N1—C1—C6	−173.9 (3)
Cl1—Ru1—N1—C1	−77.7 (2)	Ru1—N1—C1—C6	2.3 (3)
Cl2—Ru1—N1—C1	101.7 (2)	C6—C1—C2—C3	172.1 (3)
N1—Ru1—N2—C8	−146.0 (2)	N1—C1—C2—C3	−2.6 (4)
N4—Ru1—N2—C8	32.3 (2)	C1—C2—C3—C4	1.5 (5)
N3—Ru1—N2—C8	−145.5 (3)	C2—C3—C4—C5	0.9 (5)
Cl1—Ru1—N2—C8	−58.9 (2)	C1—N1—C5—C4	1.4 (4)
Cl2—Ru1—N2—C8	118.3 (2)	Ru1—N1—C5—C4	−175.2 (2)
N1—Ru1—N2—C6	−28.10 (17)	C1—N1—C5—C9	−176.6 (2)
N4—Ru1—N2—C6	150.20 (17)	Ru1—N1—C5—C9	6.7 (3)
N3—Ru1—N2—C6	−27.6 (3)	C3—C4—C5—N1	−2.4 (4)
Cl1—Ru1—N2—C6	59.00 (17)	C3—C4—C5—C9	175.2 (3)
Cl2—Ru1—N2—C6	−123.79 (17)	C2—C1—C6—N2	155.6 (3)
N1—Ru1—N2—C7	90.4 (2)	N1—C1—C6—N2	−29.0 (4)
N4—Ru1—N2—C7	−91.3 (2)	C8—N2—C6—C1	159.2 (3)
N3—Ru1—N2—C7	90.9 (3)	C7—N2—C6—C1	−90.9 (3)
Cl1—Ru1—N2—C7	177.5 (2)	Ru1—N2—C6—C1	38.4 (3)
Cl2—Ru1—N2—C7	−5.3 (2)	C10—N3—C9—C5	−84.5 (3)
N1—Ru1—N3—C9	−27.51 (17)	C11—N3—C9—C5	162.3 (3)
N4—Ru1—N3—C9	154.10 (17)	Ru1—N3—C9—C5	38.8 (3)
N2—Ru1—N3—C9	−28.0 (3)	N1—C5—C9—N3	−37.7 (4)
Cl1—Ru1—N3—C9	−115.67 (17)	C4—C5—C9—N3	144.7 (3)
Cl2—Ru1—N3—C9	67.08 (17)	C16—N4—C12—C13	1.5 (4)
N1—Ru1—N3—C10	86.1 (2)	Ru1—N4—C12—C13	−176.3 (2)
N4—Ru1—N3—C10	−92.3 (2)	N4—C12—C13—C14	−2.4 (5)
N2—Ru1—N3—C10	85.6 (4)	C12—C13—C14—C15	1.3 (5)
Cl1—Ru1—N3—C10	−2.1 (2)	C13—C14—C15—C16	0.9 (5)
Cl2—Ru1—N3—C10	−179.3 (2)	C14—C15—C16—N4	−1.9 (5)
N1—Ru1—N3—C11	−147.5 (2)	C12—N4—C16—C15	0.8 (4)
N4—Ru1—N3—C11	34.1 (2)	Ru1—N4—C16—C15	178.5 (2)
N2—Ru1—N3—C11	−148.0 (3)	C22—C17—C18—C19	1.2 (6)
Cl1—Ru1—N3—C11	124.3 (2)	C23—C17—C18—C19	−176.4 (4)
Cl2—Ru1—N3—C11	−52.9 (2)	C17—C18—C19—C20	−0.8 (7)
N1—Ru1—N4—C12	135 (3)	C18—C19—C20—C21	−0.3 (7)
N3—Ru1—N4—C12	−139.5 (2)	C19—C20—C21—C22	0.8 (6)
N2—Ru1—N4—C12	41.2 (2)	C18—C17—C22—C21	−0.7 (6)
Cl1—Ru1—N4—C12	134.1 (2)	C23—C17—C22—C21	176.8 (4)
Cl2—Ru1—N4—C12	−45.3 (2)	C20—C21—C22—C17	−0.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cl1	0.96 (5)	2.87 (5)	3.583 (4)	132 (4)
C9—H9A···Cl2	0.96 (4)	2.68 (4)	3.329 (4)	125 (3)
C10—H10C···Cl1	0.97 (4)	2.68 (4)	3.057 (4)	104 (3)
C12—H12···Cl2	1.06 (4)	2.66 (4)	3.107 (3)	105 (2)
C4—H4···Cl1ⁱ	0.84 (5)	2.73 (5)	3.522 (3)	158 (4)
C14—H14···Cl2ⁱⁱ	0.97 (4)	2.65 (4)	3.606 (4)	170 (3)

Symmetry codes: (i) x−1/2, y, −z−1/2; (ii) −x−1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[RuCl₂(C₁₁H₁₉N₃)(C₅H₅N)]·C₇H₈
M_r	536.50
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	12.7109 (1), 14.1115 (2), 27.0317 (3)
V (Å³)	4848.67 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	1.20 × 1.20 × 0.90

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Empirical (using intensity measurements) (SADABS; Sheldrick, 2000)
T_min, T_max	0.374, 0.451
No. of measured, independent and observed [I > 2σ(I)] reflections	43809, 9359, 7687
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.878

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.117, 1.19
No. of reflections	9359
No. of parameters	400
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0208P)² + 13.1818P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.07, −1.86

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai & Huttner, 1994), SHELX97.

Selected geometric parameters (Å, º) top

Ru1—Cl1	2.3501 (7)	Ru1—N2	2.348 (3)
Ru1—Cl2	2.3580 (7)	Ru1—N3	2.251 (3)
Ru1—N1	1.962 (2)	Ru1—N4	2.096 (2)

Cl1—Ru1—Cl2	177.19 (3)	N1—Ru1—N3	88.47 (10)
Cl1—Ru1—N4	90.31 (7)	N2—Ru1—N3	160.57 (9)
Cl2—Ru1—N4	86.93 (7)	N1—Ru1—N4	178.38 (9)
N1—Ru1—N2	72.10 (9)

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[mer,trans-(NN'N)RuCl2(NC5H5)]·C7H8 {NN'N = 2,6-bis-[(di­methyl­amino)­methyl]­pyridine}

Supporting information

Key indicators

checkCIF results

[mer,trans-(NN'N)RuCl₂(NC₅H₅)]·C₇H₈ {NN'N = 2,6-bis-[(dimethylamino)methyl]pyridine}