cis,cis,cis-Di­chlorido­bis­(N4,N4-di­methyl­pyridin-4-amine-κN1)bis­(dimethyl sulfoxide-κS)ruthenium(II)

Park, E.H.; Ortiz, S.M.; Liang, T.K.; Smucker, B.W.

doi:10.1107/S2414314624001913

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 3| March 2024| x240191

https://doi.org/10.1107/S2414314624001913

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cis,cis,cis-Dichloridobis(N⁴,N⁴-dimethylpyridin-4-amine-κN¹)bis(dimethyl sulfoxide-κS)ruthenium(II)

Esther H. Park,^a Sarah M. Ortiz,^a Todd K. Liang ^a and Bradley W. Smucker ^a ^*

^aAustin College, 900 N Grand, Sherman, TX 75090, USA
^*Correspondence e-mail: bsmucker@austincollege.edu

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 30 January 2024; accepted 27 February 2024; online 6 March 2024)

The structure of the title compound, [RuCl₂(C₇H₁₀N₂)₂(C₂H₆OS)₂], has monoclinic (P2₁/n) symmetry. The Ru—N distances of the coordination compound are influenced by the trans chloride or dimethylsulfoxide-κS ligands. The molecular structure exhibits disorder for two of the terminal methyl groups of a dimethyl sulfoxide ligand.

Keywords: crystal structure; coordination compound; ruthenium(II); DMAP; dmso.

CCDC reference: 2034089

Structure description

Both symmetry-related Δ and Λ enantiomers are present in the unit cell. The ruthenium(II) complex has the oxygen atoms of the dimethyl sulfoxide (dmso) ligands positioned in the same general direction toward an H1 atom of a DMAP (N,N-dimethylpyridin-4-amine) ligand with intramolecular distances of 2.456 (H1⋯O2) and 2.707 Å (H1⋯O1) (Fig. 1). The two DMAP ligands are both tilted to position the α-hydrogen atoms of the pyridyl rings to interact with the aforementioned oxygen atoms of the dmso ligand or the chlorido ligands with distances of 2.841 (H12⋯Cl2) and 2.931 Å (H12⋯Cl1) (Fig. 1). A comparison between the Ru—N distances for the coordinating DMAP ligands reveals a greater trans-influence by the S atom from the dmso ligand [Ru—N3 = 2.150 (4) Å] than by the chloride ligand [Ru—N1 = 2.117 (5) Å]. This influence by the S and Cl atoms agrees with the Ru—N distances found in the crystal structure of a similar Ru^II complex containing pyridine instead of DMAP, namely cis,cis,cis-[RuCl₂(dmso-κS)₂(py)₂] (Trivedi et al., 2010 ).

Figure 1
Displacement ellipsoid (50% probability level) representation of the title complex with intramolecular H⋯O and H⋯Cl distances given (disorder and methyl hydrogen atoms omitted for clarity).

The molecular complexes pack with one of the DMAP ligands offset above its symmetry-related counterpart, with intermolecular distances of 3.691 (9) and 3.729 (8) Å, for N2⋯C3(1 − x, 1 − y, 1 − z) and N2⋯N2(1 − x, 1 − y, 1 − z), respectively (Fig. 2).

Figure 2
Displacement ellipsoid (50% probability level) representation of the packing of two molecules of the title complex with intermolecular distances given between the N2 atom and the C3 and N2 symmetry-related atoms (1 − x, 1 − y, 1 − z). Disorder and hydrogen atoms omitted for clarity.

Synthesis and crystallization

The formation of [Ru(DMAP)₆]Cl₂ was reported from the reaction of a fortyfold excess of DMAP with [Ru(dmso)₄Cl₂] in ethanol (Rossi et al., 2008 ). With the aim toward the neutral tetrakis(DMAP) product, a general synthesis was followed, as described for trans-[RuCl₂(pyrazine-κN)₄] (Carlucci et al., 2002 ), where [RuCl₂(dmso)₄] and four equivalents of a pyridyl-based ligand are heated in toluene for multiple hours. This method has yielded trans-[RuCl₂(NN)₄] compounds with NN = 4-methoxypyridine (Reinheimer et al., 2023 ) or pyrazine (Nesterov et al., 2012 ). Rath and co-workers explored the effects of solvent polarity on the substitution of dmso and used a water/methanol solution of [Ru(dmso)₄Cl₂] and two equivalents of pyridine to form cis,cis,cis-[RuCl₂(dmso-κS)₂(py)₂] (Trivedi et al., 2010). Unexpectedly, the title compound was synthesized using a non-polar solvent and four equivalents of a more basic pyridyl-type ligand, DMAP.

A Schlenk flask was charged with 0.1 g (0.2 mmol) of Ru(dmso)₄Cl₂ and 0.1 g (0.8 mmol) of DMAP, then combined with 20 ml of toluene. The flask was purged with N₂ and the solution heated at reflux for 2 h. After slowly cooling, 0.11 g (90%) of a light-yellow solid was isolated after filtering in air and washing with ethanol. Brown prisms were grown by vapor diffusion between toluene and a chloroform/toluene solution of the product.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The crystal was treated as a two-component twin with scales of 0.9262 (9) and 0.0738 (9). Two of the terminal methyl groups were modeled for disorder using restrained distances (SADI; same distances with standard deviation of 0.02 Å) for S1—C15 and S1—C16, with parts A and B, restraining these carbon atoms with roughly equivalent anisotropic displacement parameters (SIMU; similar U_ij components with standard deviation of 0.001 Å²), and summing the occupancies of each type of C to sum to one (FVAR and 1 - FVAR; Sheldrick, 2015b ).

Table 1
Experimental details

Crystal data
Chemical formula	[RuCl₂(C₇H₁₀N₂)₂(C₂H₆OS)₂]
M_r	572.56
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.3125 (1), 18.9072 (4), 15.7906 (3)
β (°)	90.617 (2)
V (Å³)	2481.60 (8)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.04
Crystal size (mm)	0.16 × 0.10 × 0.07

Data collection
Diffractometer	XtaLAB Mini II
Absorption correction	Analytical [CrysAlis PRO (Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ) based on Clark & Reid (1995 )]
T_min, T_max	0.969, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	122167, 5695, 4795
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.148, 1.09
No. of reflections	5695
No. of parameters	293
No. of restraints	18
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.35, −0.87
Computer programs: CrysAlis PRO (Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009 ), and Mercury (Macrae et al., 2020 ).

Structural data

CCDC reference: 2034089

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624001913/bh4082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624001913/bh4082Isup2.hkl

checkCIF report

Computing details top

cis,cis,cis-Dichloridobis(N⁴,N⁴-dimethylpyridin-4-amine-κN¹)bis(dimethyl sulfoxide-κS)ruthenium(II) top

Crystal data top

[RuCl₂(C₇H₁₀N₂)₂(C₂H₆OS)₂]	F(000) = 1176
M_r = 572.56	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.3125 (1) Å	Cell parameters from 31352 reflections
b = 18.9072 (4) Å	θ = 2.2–28.7°
c = 15.7906 (3) Å	µ = 1.04 mm⁻¹
β = 90.617 (2)°	T = 293 K
V = 2481.60 (8) Å³	Block, brown
Z = 4	0.16 × 0.10 × 0.07 mm

Data collection top

XtaLAB Mini II diffractometer	4795 reflections with I > 2σ(I)
Radiation source: fine-focused sealed tube	R_int = 0.067
ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: analytical [CrysAlisPro (Rigaku OD, 2020) based on Clark & Reid (1995)]	h = −10→10
T_min = 0.969, T_max = 0.984	k = −24→24
122167 measured reflections	l = −20→20
5695 independent reflections

Refinement top

Refinement on F²	18 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.0631P)² + 9.1602P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
5695 reflections	Δρ_max = 1.35 e Å⁻³
293 parameters	Δρ_min = −0.87 e Å⁻³

Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ru1	0.73027 (5)	0.72633 (2)	0.75951 (3)	0.03186 (13)
S2	0.59464 (17)	0.71392 (7)	0.88155 (8)	0.0373 (3)
Cl2	0.88050 (19)	0.82299 (8)	0.82624 (10)	0.0511 (4)
S1	0.91252 (18)	0.64259 (9)	0.79645 (11)	0.0499 (4)
Cl1	0.8805 (2)	0.74749 (10)	0.63031 (10)	0.0531 (4)
O1	0.8687 (6)	0.5892 (2)	0.8604 (3)	0.0576 (12)
O2	0.4730 (5)	0.6575 (2)	0.8889 (3)	0.0524 (11)
N3	0.5583 (5)	0.8030 (2)	0.7148 (3)	0.0339 (9)
N2	0.3047 (7)	0.5048 (3)	0.5567 (4)	0.0571 (14)
N4	0.2210 (7)	0.9497 (3)	0.6181 (4)	0.0508 (12)
N1	0.5925 (6)	0.6498 (2)	0.6931 (3)	0.0404 (10)
C9	0.2838 (7)	0.8364 (3)	0.6840 (3)	0.0404 (12)
H9	0.175319	0.824777	0.687201	0.048*
C8	0.3974 (7)	0.7900 (3)	0.7130 (4)	0.0381 (11)
H8	0.362395	0.746412	0.732970	0.046*
C3	0.3963 (8)	0.5519 (3)	0.6005 (4)	0.0453 (13)
C10	0.3299 (7)	0.9020 (3)	0.6492 (3)	0.0405 (12)
C5	0.5422 (7)	0.6618 (3)	0.6125 (3)	0.0410 (12)
H5	0.575206	0.703469	0.586635	0.049*
C12	0.6030 (7)	0.8656 (3)	0.6827 (4)	0.0434 (13)
H12	0.712162	0.876319	0.682320	0.052*
C11	0.4969 (7)	0.9152 (3)	0.6503 (4)	0.0461 (14)
H11	0.536018	0.957625	0.628999	0.055*
C14	0.2713 (10)	1.0068 (4)	0.5618 (5)	0.0648 (19)
H14A	0.378701	1.021287	0.576635	0.097*
H14B	0.199495	1.046257	0.567635	0.097*
H14C	0.268760	0.990457	0.504287	0.097*
C1	0.5460 (8)	0.5873 (3)	0.7265 (4)	0.0463 (13)
H1	0.579416	0.576580	0.781458	0.056*
C2	0.4523 (8)	0.5385 (3)	0.6841 (4)	0.0498 (14)
H2	0.425382	0.496277	0.710649	0.060*
C4	0.4461 (8)	0.6169 (3)	0.5664 (4)	0.0469 (14)
H4	0.413423	0.629550	0.511941	0.056*
C17	0.7239 (9)	0.7070 (4)	0.9729 (4)	0.0544 (16)
H17A	0.783317	0.663560	0.970460	0.082*
H17B	0.660093	0.707661	1.023245	0.082*
H17C	0.797394	0.746193	0.973982	0.082*
C7	0.2353 (11)	0.5231 (4)	0.4753 (5)	0.070 (2)
H7A	0.132824	0.545369	0.483275	0.105*
H7B	0.221327	0.480997	0.442004	0.105*
H7C	0.305776	0.555062	0.446397	0.105*
C13	0.0489 (8)	0.9328 (4)	0.6152 (5)	0.0585 (17)
H13A	0.025195	0.905823	0.565108	0.088*
H13B	−0.012379	0.975811	0.614316	0.088*
H13C	0.021278	0.905643	0.664343	0.088*
C6	0.2547 (10)	0.4391 (4)	0.5945 (5)	0.0665 (19)
H6A	0.347232	0.414532	0.616460	0.100*
H6B	0.202125	0.410330	0.552418	0.100*
H6C	0.181547	0.448616	0.639694	0.100*
C18	0.4956 (10)	0.7942 (4)	0.9103 (4)	0.0586 (18)
H18A	0.568704	0.833165	0.904579	0.088*
H18B	0.460866	0.791123	0.967999	0.088*
H18C	0.403896	0.801449	0.873846	0.088*
C16B	1.115 (3)	0.674 (3)	0.811 (4)	0.094 (9)	0.49 (7)
H16A	1.151237	0.695361	0.759029	0.141*	0.49 (7)
H16B	1.184112	0.635662	0.825903	0.141*	0.49 (7)
H16C	1.117362	0.709174	0.855091	0.141*	0.49 (7)
C15B	0.971 (3)	0.5886 (13)	0.7074 (8)	0.107 (7)	0.89 (5)
H15A	0.879157	0.562820	0.686573	0.161*	0.89 (5)
H15B	1.053119	0.555928	0.725013	0.161*	0.89 (5)
H15C	1.011517	0.618346	0.663205	0.161*	0.89 (5)
C16A	1.088 (4)	0.684 (2)	0.843 (3)	0.094 (9)	0.51 (7)
H16D	1.113528	0.726098	0.811056	0.141*	0.51 (7)
H16E	1.177123	0.652033	0.840928	0.141*	0.51 (7)
H16F	1.066494	0.696755	0.900281	0.141*	0.51 (7)
C15A	1.026 (19)	0.625 (9)	0.702 (5)	0.107 (7)	0.11 (5)
H15D	0.989372	0.655770	0.657266	0.161*	0.11 (5)
H15E	1.010593	0.576730	0.685221	0.161*	0.11 (5)
H15F	1.138045	0.633495	0.713066	0.161*	0.11 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.0324 (2)	0.0340 (2)	0.02915 (19)	−0.00073 (16)	0.00050 (15)	0.00225 (15)
S2	0.0387 (7)	0.0418 (7)	0.0313 (6)	−0.0010 (5)	0.0018 (5)	0.0026 (5)
Cl2	0.0518 (8)	0.0528 (8)	0.0486 (8)	−0.0152 (7)	−0.0079 (6)	−0.0009 (6)
S1	0.0385 (7)	0.0533 (9)	0.0580 (9)	0.0114 (6)	0.0036 (7)	0.0098 (7)
Cl1	0.0510 (9)	0.0664 (9)	0.0421 (7)	−0.0077 (7)	0.0132 (6)	0.0031 (7)
O1	0.062 (3)	0.043 (2)	0.068 (3)	0.011 (2)	0.002 (2)	0.011 (2)
O2	0.047 (2)	0.061 (3)	0.050 (2)	−0.014 (2)	0.0099 (19)	0.001 (2)
N3	0.032 (2)	0.037 (2)	0.033 (2)	−0.0018 (18)	−0.0031 (17)	0.0026 (17)
N2	0.067 (4)	0.043 (3)	0.060 (3)	−0.015 (3)	−0.012 (3)	0.000 (2)
N4	0.054 (3)	0.041 (3)	0.057 (3)	0.008 (2)	−0.010 (3)	0.004 (2)
N1	0.049 (3)	0.036 (2)	0.037 (2)	−0.002 (2)	−0.003 (2)	0.0021 (19)
C9	0.035 (3)	0.047 (3)	0.039 (3)	−0.003 (2)	−0.003 (2)	0.002 (2)
C8	0.036 (3)	0.036 (3)	0.042 (3)	−0.005 (2)	0.000 (2)	0.007 (2)
C3	0.051 (3)	0.038 (3)	0.048 (3)	−0.005 (3)	−0.003 (3)	0.001 (2)
C10	0.048 (3)	0.037 (3)	0.036 (3)	0.002 (2)	−0.005 (2)	−0.001 (2)
C5	0.053 (3)	0.036 (3)	0.034 (3)	−0.006 (2)	−0.001 (2)	0.003 (2)
C12	0.040 (3)	0.037 (3)	0.053 (3)	−0.008 (2)	−0.003 (3)	0.007 (2)
C11	0.046 (3)	0.032 (3)	0.060 (4)	−0.007 (2)	−0.008 (3)	0.009 (2)
C14	0.073 (5)	0.045 (4)	0.076 (5)	0.002 (3)	−0.025 (4)	0.014 (3)
C1	0.061 (4)	0.038 (3)	0.040 (3)	−0.004 (3)	0.000 (3)	0.006 (2)
C2	0.064 (4)	0.037 (3)	0.048 (3)	−0.008 (3)	−0.002 (3)	0.007 (2)
C4	0.058 (4)	0.043 (3)	0.039 (3)	−0.003 (3)	−0.007 (3)	0.005 (2)
C17	0.068 (4)	0.063 (4)	0.032 (3)	0.001 (3)	−0.010 (3)	0.008 (3)
C7	0.075 (5)	0.065 (5)	0.070 (5)	−0.015 (4)	−0.025 (4)	−0.001 (4)
C13	0.046 (3)	0.059 (4)	0.071 (4)	0.012 (3)	−0.012 (3)	−0.002 (3)
C6	0.072 (5)	0.049 (4)	0.078 (5)	−0.019 (4)	−0.009 (4)	0.000 (3)
C18	0.078 (5)	0.054 (4)	0.044 (3)	0.021 (3)	0.012 (3)	0.000 (3)
C16B	0.014 (6)	0.081 (12)	0.19 (3)	0.005 (9)	0.009 (10)	0.041 (16)
C15B	0.156 (13)	0.095 (13)	0.072 (6)	0.079 (11)	0.040 (7)	0.004 (7)
C16A	0.014 (6)	0.081 (12)	0.19 (3)	0.005 (9)	0.009 (10)	0.041 (16)
C15A	0.156 (13)	0.095 (13)	0.072 (6)	0.079 (12)	0.040 (7)	0.004 (7)

Geometric parameters (Å, º) top

Ru1—S2	2.2553 (14)	C11—H11	0.9300
Ru1—Cl2	2.4456 (15)	C14—H14A	0.9600
Ru1—S1	2.2635 (15)	C14—H14B	0.9600
Ru1—Cl1	2.4366 (15)	C14—H14C	0.9600
Ru1—N3	2.150 (4)	C1—H1	0.9300
Ru1—N1	2.117 (5)	C1—C2	1.376 (9)
S2—O2	1.476 (4)	C2—H2	0.9300
S2—C17	1.794 (6)	C4—H4	0.9300
S2—C18	1.788 (6)	C17—H17A	0.9600
S1—O1	1.476 (5)	C17—H17B	0.9600
S1—C16B	1.799 (13)	C17—H17C	0.9600
S1—C15B	1.809 (9)	C7—H7A	0.9600
S1—C16A	1.804 (14)	C7—H7B	0.9600
S1—C15A	1.804 (18)	C7—H7C	0.9600
N3—C8	1.360 (7)	C13—H13A	0.9600
N3—C12	1.341 (7)	C13—H13B	0.9600
N2—C3	1.355 (8)	C13—H13C	0.9600
N2—C7	1.446 (9)	C6—H6A	0.9600
N2—C6	1.442 (9)	C6—H6B	0.9600
N4—C10	1.364 (7)	C6—H6C	0.9600
N4—C14	1.463 (9)	C18—H18A	0.9600
N4—C13	1.466 (8)	C18—H18B	0.9600
N1—C5	1.355 (7)	C18—H18C	0.9600
N1—C1	1.352 (7)	C16B—H16A	0.9600
C9—H9	0.9300	C16B—H16B	0.9600
C9—C8	1.366 (8)	C16B—H16C	0.9600
C9—C10	1.412 (8)	C15B—H15A	0.9600
C8—H8	0.9300	C15B—H15B	0.9600
C3—C2	1.419 (9)	C15B—H15C	0.9600
C3—C4	1.406 (8)	C16A—H16D	0.9600
C10—C11	1.410 (8)	C16A—H16E	0.9600
C5—H5	0.9300	C16A—H16F	0.9600
C5—C4	1.370 (8)	C15A—H15D	0.9600
C12—H12	0.9300	C15A—H15E	0.9600
C12—C11	1.381 (8)	C15A—H15F	0.9600

S2—Ru1—Cl2	88.12 (5)	N4—C14—H14C	109.5
S2—Ru1—S1	92.66 (6)	H14A—C14—H14B	109.5
S2—Ru1—Cl1	176.35 (6)	H14A—C14—H14C	109.5
S1—Ru1—Cl2	94.27 (6)	H14B—C14—H14C	109.5
S1—Ru1—Cl1	89.02 (6)	N1—C1—H1	118.0
Cl1—Ru1—Cl2	88.52 (6)	N1—C1—C2	123.9 (6)
N3—Ru1—S2	90.81 (12)	C2—C1—H1	118.0
N3—Ru1—Cl2	88.40 (12)	C3—C2—H2	119.6
N3—Ru1—S1	175.69 (12)	C1—C2—C3	120.8 (5)
N3—Ru1—Cl1	87.66 (12)	C1—C2—H2	119.6
N1—Ru1—S2	94.54 (13)	C3—C4—H4	119.6
N1—Ru1—Cl2	174.55 (13)	C5—C4—C3	120.7 (5)
N1—Ru1—S1	90.36 (14)	C5—C4—H4	119.6
N1—Ru1—Cl1	88.68 (14)	S2—C17—H17A	109.5
N1—Ru1—N3	86.82 (18)	S2—C17—H17B	109.5
O2—S2—Ru1	119.47 (19)	S2—C17—H17C	109.5
O2—S2—C17	106.8 (3)	H17A—C17—H17B	109.5
O2—S2—C18	106.0 (3)	H17A—C17—H17C	109.5
C17—S2—Ru1	113.2 (2)	H17B—C17—H17C	109.5
C18—S2—Ru1	111.4 (2)	N2—C7—H7A	109.5
C18—S2—C17	97.5 (3)	N2—C7—H7B	109.5
O1—S1—Ru1	119.0 (2)	N2—C7—H7C	109.5
O1—S1—C16B	112 (2)	H7A—C7—H7B	109.5
O1—S1—C15B	102.5 (9)	H7A—C7—H7C	109.5
O1—S1—C16A	103.1 (19)	H7B—C7—H7C	109.5
O1—S1—C15A	125 (5)	N4—C13—H13A	109.5
C16B—S1—Ru1	114.9 (18)	N4—C13—H13B	109.5
C16B—S1—C15B	92 (2)	N4—C13—H13C	109.5
C15B—S1—Ru1	112.3 (5)	H13A—C13—H13B	109.5
C16A—S1—Ru1	109.5 (16)	H13A—C13—H13C	109.5
C15A—S1—Ru1	106 (4)	H13B—C13—H13C	109.5
C15A—S1—C16A	89 (7)	N2—C6—H6A	109.5
C8—N3—Ru1	122.3 (4)	N2—C6—H6B	109.5
C12—N3—Ru1	122.2 (4)	N2—C6—H6C	109.5
C12—N3—C8	115.4 (5)	H6A—C6—H6B	109.5
C3—N2—C7	120.9 (6)	H6A—C6—H6C	109.5
C3—N2—C6	121.2 (6)	H6B—C6—H6C	109.5
C6—N2—C7	117.4 (6)	S2—C18—H18A	109.5
C10—N4—C14	120.9 (6)	S2—C18—H18B	109.5
C10—N4—C13	120.7 (5)	S2—C18—H18C	109.5
C14—N4—C13	115.3 (5)	H18A—C18—H18B	109.5
C5—N1—Ru1	120.7 (4)	H18A—C18—H18C	109.5
C1—N1—Ru1	124.0 (4)	H18B—C18—H18C	109.5
C1—N1—C5	115.3 (5)	S1—C16B—H16A	109.5
C8—C9—H9	119.8	S1—C16B—H16B	109.5
C8—C9—C10	120.4 (5)	S1—C16B—H16C	109.5
C10—C9—H9	119.8	H16A—C16B—H16B	109.5
N3—C8—C9	124.5 (5)	H16A—C16B—H16C	109.5
N3—C8—H8	117.7	H16B—C16B—H16C	109.5
C9—C8—H8	117.7	S1—C15B—H15A	109.5
N2—C3—C2	122.3 (6)	S1—C15B—H15B	109.5
N2—C3—C4	123.0 (6)	S1—C15B—H15C	109.5
C4—C3—C2	114.7 (5)	H15A—C15B—H15B	109.5
N4—C10—C9	122.6 (5)	H15A—C15B—H15C	109.5
N4—C10—C11	122.5 (5)	H15B—C15B—H15C	109.5
C11—C10—C9	114.9 (5)	S1—C16A—H16D	109.5
N1—C5—H5	117.7	S1—C16A—H16E	109.5
N1—C5—C4	124.6 (5)	S1—C16A—H16F	109.5
C4—C5—H5	117.7	H16D—C16A—H16E	109.5
N3—C12—H12	117.9	H16D—C16A—H16F	109.5
N3—C12—C11	124.1 (5)	H16E—C16A—H16F	109.5
C11—C12—H12	117.9	S1—C15A—H15D	109.5
C10—C11—H11	119.7	S1—C15A—H15E	109.5
C12—C11—C10	120.6 (5)	S1—C15A—H15F	109.5
C12—C11—H11	119.7	H15D—C15A—H15E	109.5
N4—C14—H14A	109.5	H15D—C15A—H15F	109.5
N4—C14—H14B	109.5	H15E—C15A—H15F	109.5

Ru1—N3—C8—C9	−178.9 (4)	C10—C9—C8—N3	3.1 (9)
Ru1—N3—C12—C11	177.3 (5)	C5—N1—C1—C2	−1.0 (9)
Ru1—N1—C5—C4	−176.6 (5)	C12—N3—C8—C9	−2.1 (8)
Ru1—N1—C1—C2	177.9 (5)	C14—N4—C10—C9	−162.6 (6)
N3—C12—C11—C10	0.0 (10)	C14—N4—C10—C11	18.7 (9)
N2—C3—C2—C1	179.6 (6)	C1—N1—C5—C4	2.4 (9)
N2—C3—C4—C5	−178.3 (6)	C2—C3—C4—C5	0.5 (9)
N4—C10—C11—C12	179.6 (6)	C4—C3—C2—C1	0.8 (10)
N1—C5—C4—C3	−2.2 (10)	C7—N2—C3—C2	173.3 (7)
N1—C1—C2—C3	−0.6 (10)	C7—N2—C3—C4	−8.0 (11)
C9—C10—C11—C12	0.8 (9)	C13—N4—C10—C9	−3.5 (9)
C8—N3—C12—C11	0.6 (9)	C13—N4—C10—C11	177.7 (6)
C8—C9—C10—N4	178.9 (6)	C6—N2—C3—C2	2.0 (11)
C8—C9—C10—C11	−2.2 (8)	C6—N2—C3—C4	−179.3 (7)

Funding information

Funding for this research was provided by: Welch Foundation (grant No. AD-0007 to the Chemistry Department); Jerry Taylor and Nancy Bryant Foundation (gift to the Austin College Science Division).

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