trans-Carbon­yl[dihydro­bis(1,2,4-triazol-1-yl-κN2)borato]hydridobis(triphenyl­phosphine-κP)ruthenium(II) acetonitrile solvate

Huh, S.

doi:10.1107/S160053680706792X

metal-organic compounds

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Volume 64| Part 2| February 2008| Page m290

doi:10.1107/S160053680706792X

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trans-Carbonyl[dihydrobis(1,2,4-triazol-1-yl-κN²)borato]hydridobis(triphenylphosphine-κP)ruthenium(II) acetonitrile solvate

Seong Huh ^a ^*

^aDepartment of Chemistry, Hankuk University of Foreign Studies, Yongin 449-791, Republic of Korea
^*Correspondence e-mail: shuh@hufs.ac.kr

(Received 10 November 2007; accepted 20 December 2007; online 4 January 2008)

In the crystal structure of the title compound, [Ru(C₄H₆BN₆)H(C₁₈H₁₅P)₂(CO)]·C₂H₃N, discrete mononuclear complexes are found in which the Ru atom is coordinated by two triphenylphosphine (PPh₃) ligands, one dihydrobis(1,2,4-triazol-1-yl)borate ligand, one carbonyl ligand and one hydride atom within slightly distorted octahedra. The two P atoms of the PPh₃ ligands are trans positioned and the two N atoms of the chelating dihydrobis(1,2,4-triazol-1-yl)borate ligand occupy cis positions.

Related literature

For related literature, see: Youm et al. (2006 ); Huh et al. (1999 , 2000 ).

Experimental

Crystal data

[Ru(C₄H₆BN₆)H(C₁₈H₁₅P)₂(CO)]·C₂H₃N
M_r = 844.64
Triclinic, $[P \overline 1]$
a = 9.0733 (1) Å
b = 11.8032 (3) Å
c = 20.2609 (6) Å
α = 74.438 (11)°
β = 89.552 (15)°
γ = 70.731 (14)°
V = 1965.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 100 (2) K
0.35 × 0.30 × 0.28 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997 ) T_min = 0.838, T_max = 0.867
31908 measured reflections
8964 independent reflections
6896 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.079
S = 0.98
8964 reflections
521 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ru1—H1RU	1.57 (2)
Ru1—C1	1.833 (2)
Ru1—N4	2.1396 (19)
Ru1—N1	2.1771 (17)
Ru1—P2	2.3588 (6)
Ru1—P1	2.3978 (6)

H1RU—Ru1—C1	90.0 (9)
H1RU—Ru1—N4	87.9 (9)
C1—Ru1—N4	176.92 (8)
H1RU—Ru1—N1	175.7 (9)
C1—Ru1—N1	94.31 (8)
N4—Ru1—N1	87.84 (7)
H1RU—Ru1—P2	81.0 (8)
C1—Ru1—P2	86.77 (7)
N4—Ru1—P2	95.09 (5)
N1—Ru1—P2	98.90 (5)
H1RU—Ru1—P1	91.1 (8)
C1—Ru1—P1	91.65 (7)
N4—Ru1—P1	86.16 (5)
N1—Ru1—P1	89.15 (5)
P2—Ru1—P1	171.884 (18)

Data collection: KappaCCD Server Software (Nonius, 1997 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Bruker, 1998 ); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706792X/nc2075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680706792X/nc2075Isup2.hkl

checkCIF report

Comment top

In our ongoing investigations on the preparation of one-dimensional coordination polymers containing catalytically active Ru^II complex moieties, we recently reported the preparation and spectroscopic data of the title compound (I) (Youm et al., 2006). The proposed structure of (I) which based on the spectroscopic data closely resembles those of the previously structurally characterized analogues, [RuH(AsPh₃)₂(η²-H₂Bpz₂)(CO)] (II) (pz is pyrazol-1-yl) (Huh et al., 1999) and [RuH{P(p-C₆H₄CH₃)₃}₂(η²-H₂Bpz₂)(CO)] (III) (Huh et al., 2000). Here we report the crystal structure of compound (I).

The crystal structure of compound I shows similar structural features as the analogous structures of (II) and (III) and therefore, confirm the proposed structure of (I) from our spectroscopic investigations.

In the crystal structure of the title compound the Ru atom is coordinated by two phosphorous atoms of two crystallographically independent triphenylphosphine ligands, one carbon atom of the CO ligand, one hydride H atom and two nitrogen atoms of the dihydrobis(1,2,4-triazol-1-yl)borate ligand within a slightly distorted octahedra (Fig. 1). The two phosphorous atoms of the PPh₃ ligands are trans-positioned and the two nitrogen atoms of the chelating dihydrobis(1,2,4-triazol-1-yl)borate ligand occupy cis-positions. The two Ru—P bond lengths are slightly longer than those in (III) [2.3448 (17) – 2.3699 (17) Å] (Tab. 1). In (I), the Ru1—P1 bond length is slightly longer than the Ru1—P2 bond by about 0.039 Å (Tab. 1). However, the Ru—N bond distances are very similar to those in (III). The H1—Ru—P2 angle of 81.0 (8)° is smaller than the H1—Ru—P1 angle of 91.1 (8)° (Tab. 1).

Related literature top

For related literature, see: Youm et al. (2006); Huh et al. (1999, 2000).

Experimental top

The title compound was prepared according to the literature method (Youm et al., 2006). Single crystals are obtained by slow evaporation of the solvent from a solution of (I) in acetonitrile.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Bruker, 1998); software used to prepare material for publication: SHELXTL/PC (Bruker, 1998).

Figures top

Fig. 1. The molecular structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level. All hydrogen atoms except the hydride and hydrogen atoms attached to the B atom are omitted for clarity.

trans-Carbonyl[dihydrobis(1,2,4-triazol-1-yl- κN²)borato]hydridobis(triphenylphosphine-κP)ruthenium(II) acetonitrile solvate top

Crystal data top

[Ru(C₄H₆BN₆)H(C₁₈H₁₅P)₂(CO)]·C₂H₃N	Z = 2
M_r = 844.64	F(000) = 868
Triclinic, P1	D_x = 1.427 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0733 (1) Å	Cell parameters from 31908 reflections
b = 11.8032 (3) Å	θ = 4.1–27.5°
c = 20.2609 (6) Å	µ = 0.53 mm⁻¹
α = 74.438 (11)°	T = 100 K
β = 89.552 (15)°	Block cut from needle, pale yellow
γ = 70.731 (14)°	0.35 × 0.30 × 0.28 mm
V = 1965.4 (2) Å³

Data collection top

Nonius KappaCCD diffractometer	8964 independent reflections
Radiation source: fine-focus sealed tube	6896 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 4.1°
ϕ scan and ω scans with κ offsets	h = −11→11
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	k = −13→15
T_min = 0.838, T_max = 0.867	l = −26→26
31908 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0387P)²] where P = (F_o² + 2F_c²)/3
8964 reflections	(Δ/σ)_max = 0.002
521 parameters	Δρ_max = 0.76 e Å⁻³
9 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

[Ru(C₄H₆BN₆)H(C₁₈H₁₅P)₂(CO)]·C₂H₃N	γ = 70.731 (14)°
M_r = 844.64	V = 1965.4 (2) Å³
Triclinic, P1	Z = 2
a = 9.0733 (1) Å	Mo Kα radiation
b = 11.8032 (3) Å	µ = 0.53 mm⁻¹
c = 20.2609 (6) Å	T = 100 K
α = 74.438 (11)°	0.35 × 0.30 × 0.28 mm
β = 89.552 (15)°

Data collection top

Nonius KappaCCD diffractometer	8964 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	6896 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.867	R_int = 0.060
31908 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	9 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.76 e Å⁻³
8964 reflections	Δρ_min = −0.79 e Å⁻³
521 parameters

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	0.991567 (18)	0.597576 (15)	0.723224 (10)	0.01409 (6)
H1RU	0.815 (2)	0.668 (2)	0.6948 (12)	0.022 (6)*
P1	0.97691 (6)	0.40525 (5)	0.71054 (3)	0.01384 (12)
P2	0.97123 (6)	0.80041 (5)	0.72650 (3)	0.01507 (12)
O1	1.09179 (19)	0.66608 (15)	0.58094 (9)	0.0295 (4)
N1	1.23032 (19)	0.49727 (16)	0.77038 (10)	0.0160 (4)
N2	1.2776 (2)	0.46297 (17)	0.83893 (10)	0.0194 (4)
N3	1.4870 (2)	0.38206 (18)	0.78677 (11)	0.0251 (5)
N4	0.91255 (19)	0.54559 (16)	0.82298 (10)	0.0162 (4)
N5	1.0082 (2)	0.49179 (16)	0.88370 (10)	0.0195 (4)
N6	0.7751 (2)	0.47449 (18)	0.90769 (11)	0.0267 (5)
C1	1.0512 (2)	0.63962 (19)	0.63591 (13)	0.0181 (5)
C2	1.3590 (2)	0.44611 (19)	0.74159 (12)	0.0195 (5)
H2A	1.3604	0.4540	0.6937	0.023*
C3	1.4305 (2)	0.3955 (2)	0.84596 (13)	0.0266 (6)
H3A	1.4923	0.3607	0.8889	0.032*
C4	0.7767 (2)	0.5315 (2)	0.84039 (13)	0.0212 (5)
H4A	0.6879	0.5592	0.8081	0.025*
C5	0.9212 (3)	0.4511 (2)	0.93188 (13)	0.0258 (5)
H5A	0.9600	0.4098	0.9786	0.031*
C11	1.0065 (2)	0.28484 (19)	0.79288 (12)	0.0161 (4)
C12	0.8863 (2)	0.2443 (2)	0.82195 (12)	0.0200 (5)
H12A	0.7859	0.2746	0.7974	0.024*
C13	0.9140 (3)	0.1595 (2)	0.88699 (13)	0.0254 (5)
H13A	0.8317	0.1326	0.9067	0.031*
C14	1.0599 (3)	0.1136 (2)	0.92364 (13)	0.0260 (5)
H14A	1.0778	0.0549	0.9678	0.031*
C15	1.1800 (2)	0.1544 (2)	0.89514 (13)	0.0216 (5)
H15A	1.2802	0.1241	0.9200	0.026*
C16	1.1531 (2)	0.23893 (19)	0.83086 (12)	0.0182 (5)
H16A	1.2354	0.2667	0.8118	0.022*
C21	1.1176 (2)	0.32556 (19)	0.65704 (12)	0.0165 (5)
C22	1.1077 (2)	0.3869 (2)	0.58734 (12)	0.0216 (5)
H22A	1.0322	0.4681	0.5696	0.026*
C23	1.2054 (3)	0.3322 (2)	0.54338 (13)	0.0245 (5)
H23A	1.1967	0.3757	0.4960	0.029*
C24	1.3165 (3)	0.2133 (2)	0.56868 (13)	0.0245 (5)
H24A	1.3847	0.1758	0.5388	0.029*
C25	1.3268 (3)	0.1503 (2)	0.63731 (14)	0.0298 (6)
H25A	1.4016	0.0687	0.6546	0.036*
C26	1.2285 (3)	0.2052 (2)	0.68153 (13)	0.0240 (5)
H26A	1.2367	0.1607	0.7288	0.029*
C31	0.7951 (2)	0.4155 (2)	0.66621 (11)	0.0161 (4)
C32	0.6824 (2)	0.5310 (2)	0.63387 (12)	0.0189 (5)
H32A	0.6943	0.6055	0.6386	0.023*
C33	0.5524 (2)	0.5382 (2)	0.59473 (12)	0.0221 (5)
H33A	0.4775	0.6174	0.5721	0.026*
C34	0.5322 (2)	0.4303 (2)	0.58883 (12)	0.0226 (5)
H34A	0.4429	0.4353	0.5626	0.027*
C35	0.6424 (3)	0.3145 (2)	0.62120 (13)	0.0235 (5)
H35A	0.6281	0.2403	0.6173	0.028*
C36	0.7736 (2)	0.3071 (2)	0.65924 (12)	0.0208 (5)
H36A	0.8495	0.2277	0.6807	0.025*
C41	0.9074 (2)	0.91694 (19)	0.64166 (12)	0.0177 (5)
C42	0.7850 (3)	0.9175 (2)	0.60011 (13)	0.0239 (5)
H42A	0.7373	0.8555	0.6151	0.029*
C43	0.7320 (3)	1.0073 (2)	0.53737 (13)	0.0259 (5)
H43A	0.6486	1.0064	0.5097	0.031*
C44	0.8006 (3)	1.0989 (2)	0.51474 (13)	0.0262 (5)
H44A	0.7643	1.1604	0.4717	0.031*
C45	0.9218 (3)	1.0994 (2)	0.55539 (13)	0.0244 (5)
H45A	0.9691	1.1616	0.5401	0.029*
C46	0.9751 (2)	1.0099 (2)	0.61834 (12)	0.0210 (5)
H46A	1.0582	1.0116	0.6459	0.025*
C51	1.1555 (2)	0.81957 (19)	0.74822 (12)	0.0170 (5)
C52	1.2868 (2)	0.7637 (2)	0.71679 (12)	0.0201 (5)
H52A	1.2784	0.7169	0.6864	0.024*
C53	1.4298 (2)	0.7767 (2)	0.73004 (13)	0.0230 (5)
H53A	1.5186	0.7390	0.7084	0.028*
C54	1.4430 (2)	0.8441 (2)	0.77453 (13)	0.0238 (5)
H54A	1.5413	0.8516	0.7839	0.029*
C55	1.3140 (2)	0.9007 (2)	0.80537 (13)	0.0221 (5)
H55A	1.3232	0.9478	0.8355	0.027*
C56	1.1690 (2)	0.8885 (2)	0.79220 (12)	0.0194 (5)
H56A	1.0801	0.9275	0.8134	0.023*
C61	0.8356 (2)	0.8771 (2)	0.78193 (12)	0.0182 (5)
C62	0.8375 (2)	0.8146 (2)	0.85103 (12)	0.0213 (5)
H62A	0.9069	0.7311	0.8690	0.026*
C63	0.7396 (3)	0.8727 (2)	0.89403 (14)	0.0259 (5)
H63A	0.7418	0.8290	0.9410	0.031*
C64	0.6377 (3)	0.9956 (2)	0.86808 (14)	0.0280 (6)
H64A	0.5704	1.0357	0.8974	0.034*
C65	0.6349 (3)	1.0586 (2)	0.80013 (15)	0.0283 (6)
H65A	0.5663	1.1425	0.7827	0.034*
C66	0.7322 (2)	1.0002 (2)	0.75667 (13)	0.0223 (5)
H66A	0.7283	1.0441	0.7096	0.027*
B1	1.1701 (3)	0.5070 (3)	0.89352 (15)	0.0241 (6)
H1B	1.227 (3)	0.447 (2)	0.9452 (14)	0.031 (7)*
H2B	1.147 (3)	0.615 (2)	0.8855 (13)	0.029 (7)*
N1S	0.5802 (3)	1.1379 (2)	1.00400 (13)	0.0398 (6)
C1S	0.5862 (3)	1.3314 (3)	1.04008 (15)	0.0385 (7)
C2S	0.5840 (3)	1.2214 (3)	1.02053 (13)	0.0290 (6)
H1S	0.660 (2)	1.3039 (18)	1.0804 (9)	0.044*
H2S	0.620 (2)	1.3844 (17)	1.0025 (10)	0.044*
H3S	0.483 (2)	1.3758 (17)	1.0506 (10)	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.01425 (9)	0.01286 (9)	0.01445 (11)	−0.00458 (6)	0.00124 (6)	−0.00273 (7)
P1	0.0149 (3)	0.0122 (3)	0.0137 (3)	−0.0046 (2)	0.0013 (2)	−0.0025 (2)
P2	0.0144 (3)	0.0128 (3)	0.0181 (3)	−0.0048 (2)	0.0018 (2)	−0.0045 (2)
O1	0.0422 (10)	0.0280 (9)	0.0200 (11)	−0.0163 (8)	0.0089 (8)	−0.0041 (8)
N1	0.0166 (9)	0.0157 (9)	0.0158 (11)	−0.0067 (7)	0.0022 (7)	−0.0034 (8)
N2	0.0185 (9)	0.0210 (10)	0.0162 (11)	−0.0039 (7)	−0.0015 (7)	−0.0044 (8)
N3	0.0171 (9)	0.0275 (11)	0.0251 (13)	−0.0010 (8)	−0.0002 (8)	−0.0066 (9)
N4	0.0177 (9)	0.0141 (9)	0.0158 (11)	−0.0042 (7)	0.0027 (7)	−0.0040 (8)
N5	0.0215 (9)	0.0169 (9)	0.0164 (11)	−0.0024 (7)	0.0018 (7)	−0.0040 (8)
N6	0.0318 (11)	0.0277 (11)	0.0235 (13)	−0.0134 (9)	0.0118 (9)	−0.0078 (9)
C1	0.0190 (11)	0.0122 (11)	0.0225 (14)	−0.0055 (8)	−0.0011 (9)	−0.0034 (9)
C2	0.0178 (11)	0.0192 (11)	0.0192 (13)	−0.0057 (8)	0.0037 (9)	−0.0025 (10)
C3	0.0193 (11)	0.0276 (13)	0.0260 (15)	−0.0007 (9)	−0.0055 (10)	−0.0051 (11)
C4	0.0198 (11)	0.0208 (12)	0.0243 (14)	−0.0078 (9)	0.0054 (9)	−0.0076 (10)
C5	0.0350 (13)	0.0227 (12)	0.0174 (14)	−0.0085 (10)	0.0070 (10)	−0.0035 (10)
C11	0.0204 (10)	0.0103 (10)	0.0165 (13)	−0.0038 (8)	0.0018 (8)	−0.0037 (9)
C12	0.0172 (11)	0.0192 (11)	0.0211 (14)	−0.0059 (8)	0.0013 (9)	−0.0023 (10)
C13	0.0253 (12)	0.0268 (13)	0.0226 (15)	−0.0132 (10)	0.0036 (10)	0.0009 (11)
C14	0.0300 (13)	0.0230 (12)	0.0188 (14)	−0.0080 (10)	0.0009 (10)	0.0031 (10)
C15	0.0199 (11)	0.0177 (11)	0.0226 (14)	−0.0034 (9)	−0.0010 (9)	−0.0020 (10)
C16	0.0178 (10)	0.0155 (11)	0.0203 (13)	−0.0054 (8)	0.0014 (9)	−0.0041 (9)
C21	0.0158 (10)	0.0174 (11)	0.0196 (13)	−0.0081 (8)	0.0019 (8)	−0.0072 (9)
C22	0.0229 (11)	0.0192 (12)	0.0195 (14)	−0.0038 (9)	0.0018 (9)	−0.0044 (10)
C23	0.0263 (12)	0.0294 (13)	0.0172 (14)	−0.0085 (10)	0.0052 (9)	−0.0068 (10)
C24	0.0229 (12)	0.0295 (13)	0.0271 (15)	−0.0103 (10)	0.0093 (10)	−0.0162 (11)
C25	0.0298 (13)	0.0216 (12)	0.0321 (16)	0.0003 (10)	0.0061 (11)	−0.0094 (11)
C26	0.0264 (12)	0.0182 (12)	0.0225 (14)	−0.0032 (9)	0.0033 (10)	−0.0036 (10)
C31	0.0160 (10)	0.0189 (11)	0.0134 (12)	−0.0063 (8)	0.0024 (8)	−0.0043 (9)
C32	0.0209 (11)	0.0204 (11)	0.0167 (13)	−0.0092 (9)	0.0035 (9)	−0.0046 (9)
C33	0.0170 (11)	0.0267 (12)	0.0183 (13)	−0.0045 (9)	−0.0016 (9)	−0.0033 (10)
C34	0.0207 (11)	0.0343 (14)	0.0158 (13)	−0.0133 (10)	0.0015 (9)	−0.0069 (10)
C35	0.0257 (12)	0.0263 (12)	0.0244 (14)	−0.0142 (10)	0.0043 (10)	−0.0102 (11)
C36	0.0211 (11)	0.0175 (11)	0.0221 (14)	−0.0055 (9)	0.0006 (9)	−0.0044 (10)
C41	0.0190 (10)	0.0128 (10)	0.0183 (13)	−0.0025 (8)	0.0014 (8)	−0.0029 (9)
C42	0.0255 (12)	0.0175 (11)	0.0263 (15)	−0.0063 (9)	−0.0031 (10)	−0.0034 (10)
C43	0.0230 (12)	0.0221 (12)	0.0260 (15)	−0.0005 (9)	−0.0063 (10)	−0.0049 (11)
C44	0.0309 (13)	0.0186 (12)	0.0200 (14)	0.0007 (9)	0.0015 (10)	−0.0019 (10)
C45	0.0288 (12)	0.0176 (11)	0.0245 (15)	−0.0078 (9)	0.0080 (10)	−0.0024 (10)
C46	0.0199 (11)	0.0189 (11)	0.0237 (14)	−0.0062 (9)	0.0026 (9)	−0.0056 (10)
C51	0.0168 (10)	0.0124 (10)	0.0189 (13)	−0.0044 (8)	0.0011 (8)	−0.0002 (9)
C52	0.0209 (11)	0.0164 (11)	0.0225 (14)	−0.0065 (8)	0.0013 (9)	−0.0044 (10)
C53	0.0157 (11)	0.0214 (12)	0.0303 (15)	−0.0051 (9)	0.0061 (9)	−0.0065 (11)
C54	0.0179 (11)	0.0221 (12)	0.0297 (15)	−0.0094 (9)	−0.0018 (9)	−0.0013 (10)
C55	0.0237 (11)	0.0199 (12)	0.0236 (14)	−0.0103 (9)	−0.0023 (9)	−0.0039 (10)
C56	0.0208 (11)	0.0156 (11)	0.0210 (13)	−0.0056 (8)	0.0013 (9)	−0.0045 (9)
C61	0.0131 (10)	0.0183 (11)	0.0269 (14)	−0.0068 (8)	0.0027 (9)	−0.0101 (10)
C62	0.0216 (11)	0.0217 (12)	0.0219 (14)	−0.0075 (9)	0.0032 (9)	−0.0081 (10)
C63	0.0236 (12)	0.0335 (14)	0.0270 (15)	−0.0127 (10)	0.0072 (10)	−0.0153 (11)
C64	0.0212 (12)	0.0300 (13)	0.0409 (18)	−0.0093 (10)	0.0109 (10)	−0.0225 (13)
C65	0.0219 (12)	0.0190 (12)	0.0458 (18)	−0.0062 (9)	0.0074 (11)	−0.0129 (12)
C66	0.0180 (11)	0.0164 (11)	0.0324 (15)	−0.0066 (8)	0.0059 (9)	−0.0059 (10)
B1	0.0225 (13)	0.0284 (15)	0.0204 (16)	−0.0031 (11)	−0.0001 (11)	−0.0123 (12)
N1S	0.0555 (15)	0.0322 (13)	0.0298 (15)	−0.0145 (11)	0.0069 (11)	−0.0064 (11)
C1S	0.0487 (17)	0.0355 (16)	0.0321 (18)	−0.0222 (13)	−0.0020 (13)	−0.0006 (13)
C2S	0.0287 (13)	0.0345 (15)	0.0178 (14)	−0.0105 (11)	0.0033 (10)	0.0022 (11)

Geometric parameters (Å, º) top

Ru1—H1RU	1.57 (2)	C31—C32	1.394 (3)
Ru1—C1	1.833 (2)	C31—C36	1.398 (3)
Ru1—N4	2.1396 (19)	C32—C33	1.392 (3)
Ru1—N1	2.1771 (17)	C32—H32A	0.9500
Ru1—P2	2.3588 (6)	C33—C34	1.380 (3)
Ru1—P1	2.3978 (6)	C33—H33A	0.9500
P1—C11	1.833 (2)	C34—C35	1.387 (3)
P1—C31	1.837 (2)	C34—H34A	0.9500
P1—C21	1.850 (2)	C35—C36	1.389 (3)
P2—C51	1.831 (2)	C35—H35A	0.9500
P2—C61	1.839 (2)	C36—H36A	0.9500
P2—C41	1.845 (2)	C41—C42	1.396 (3)
O1—C1	1.165 (3)	C41—C46	1.403 (3)
N1—C2	1.334 (3)	C42—C43	1.386 (3)
N1—N2	1.367 (3)	C42—H42A	0.9500
N2—C3	1.339 (3)	C43—C44	1.392 (3)
N2—B1	1.550 (3)	C43—H43A	0.9500
N3—C3	1.328 (3)	C44—C45	1.382 (3)
N3—C2	1.351 (3)	C44—H44A	0.9500
N4—C4	1.330 (3)	C45—C46	1.388 (3)
N4—N5	1.380 (2)	C45—H45A	0.9500
N5—C5	1.339 (3)	C46—H46A	0.9500
N5—B1	1.558 (3)	C51—C56	1.389 (3)
N6—C5	1.330 (3)	C51—C52	1.398 (3)
N6—C4	1.351 (3)	C52—C53	1.392 (3)
C2—H2A	0.9500	C52—H52A	0.9500
C3—H3A	0.9500	C53—C54	1.382 (3)
C4—H4A	0.9500	C53—H53A	0.9500
C5—H5A	0.9500	C54—C55	1.380 (3)
C11—C12	1.396 (3)	C54—H54A	0.9500
C11—C16	1.404 (3)	C55—C56	1.405 (3)
C12—C13	1.390 (3)	C55—H55A	0.9500
C12—H12A	0.9500	C56—H56A	0.9500
C13—C14	1.387 (3)	C61—C62	1.393 (3)
C13—H13A	0.9500	C61—C66	1.401 (3)
C14—C15	1.393 (3)	C62—C63	1.387 (3)
C14—H14A	0.9500	C62—H62A	0.9500
C15—C16	1.378 (3)	C63—C64	1.396 (3)
C15—H15A	0.9500	C63—H63A	0.9500
C16—H16A	0.9500	C64—C65	1.374 (4)
C21—C22	1.392 (3)	C64—H64A	0.9500
C21—C26	1.401 (3)	C65—C66	1.393 (3)
C22—C23	1.384 (3)	C65—H65A	0.9500
C22—H22A	0.9500	C66—H66A	0.9500
C23—C24	1.391 (3)	B1—H1B	1.11 (3)
C23—H23A	0.9500	B1—H2B	1.19 (2)
C24—C25	1.377 (3)	N1S—C2S	1.133 (3)
C24—H24A	0.9500	C1S—C2S	1.463 (4)
C25—C26	1.391 (3)	C1S—H1S	0.969 (16)
C25—H25A	0.9500	C1S—H2S	0.966 (16)
C26—H26A	0.9500	C1S—H3S	0.960 (16)

H1RU—Ru1—C1	90.0 (9)	C25—C26—H26A	119.7
H1RU—Ru1—N4	87.9 (9)	C21—C26—H26A	119.7
C1—Ru1—N4	176.92 (8)	C32—C31—C36	118.57 (19)
H1RU—Ru1—N1	175.7 (9)	C32—C31—P1	121.10 (16)
C1—Ru1—N1	94.31 (8)	C36—C31—P1	120.10 (16)
N4—Ru1—N1	87.84 (7)	C33—C32—C31	120.6 (2)
H1RU—Ru1—P2	81.0 (8)	C33—C32—H32A	119.7
C1—Ru1—P2	86.77 (7)	C31—C32—H32A	119.7
N4—Ru1—P2	95.09 (5)	C34—C33—C32	120.1 (2)
N1—Ru1—P2	98.90 (5)	C34—C33—H33A	120.0
H1RU—Ru1—P1	91.1 (8)	C32—C33—H33A	120.0
C1—Ru1—P1	91.65 (7)	C33—C34—C35	120.0 (2)
N4—Ru1—P1	86.16 (5)	C33—C34—H34A	120.0
N1—Ru1—P1	89.15 (5)	C35—C34—H34A	120.0
P2—Ru1—P1	171.884 (18)	C34—C35—C36	120.0 (2)
C11—P1—C31	106.50 (10)	C34—C35—H35A	120.0
C11—P1—C21	103.72 (10)	C36—C35—H35A	120.0
C31—P1—C21	98.22 (10)	C35—C36—C31	120.6 (2)
C11—P1—Ru1	112.79 (7)	C35—C36—H36A	119.7
C31—P1—Ru1	116.25 (7)	C31—C36—H36A	119.7
C21—P1—Ru1	117.57 (7)	C42—C41—C46	118.2 (2)
C51—P2—C61	103.14 (10)	C42—C41—P2	120.30 (17)
C51—P2—C41	101.34 (10)	C46—C41—P2	121.40 (17)
C61—P2—C41	101.84 (10)	C43—C42—C41	120.9 (2)
C51—P2—Ru1	115.45 (7)	C43—C42—H42A	119.5
C61—P2—Ru1	120.09 (7)	C41—C42—H42A	119.5
C41—P2—Ru1	112.53 (7)	C42—C43—C44	120.2 (2)
C2—N1—N2	104.51 (16)	C42—C43—H43A	119.9
C2—N1—Ru1	128.99 (15)	C44—C43—H43A	119.9
N2—N1—Ru1	126.25 (13)	C45—C44—C43	119.4 (2)
C3—N2—N1	106.52 (19)	C45—C44—H44A	120.3
C3—N2—B1	129.5 (2)	C43—C44—H44A	120.3
N1—N2—B1	123.77 (17)	C44—C45—C46	120.6 (2)
C3—N3—C2	102.03 (18)	C44—C45—H45A	119.7
C4—N4—N5	104.00 (18)	C46—C45—H45A	119.7
C4—N4—Ru1	129.70 (16)	C45—C46—C41	120.6 (2)
N5—N4—Ru1	124.89 (13)	C45—C46—H46A	119.7
C5—N5—N4	106.46 (18)	C41—C46—H46A	119.7
C5—N5—B1	128.5 (2)	C56—C51—C52	119.42 (19)
N4—N5—B1	123.62 (19)	C56—C51—P2	123.44 (16)
C5—N6—C4	101.79 (19)	C52—C51—P2	117.11 (17)
O1—C1—Ru1	178.72 (18)	C53—C52—C51	120.0 (2)
N1—C2—N3	113.9 (2)	C53—C52—H52A	120.0
N1—C2—H2A	123.1	C51—C52—H52A	120.0
N3—C2—H2A	123.1	C54—C53—C52	120.3 (2)
N3—C3—N2	113.1 (2)	C54—C53—H53A	119.8
N3—C3—H3A	123.5	C52—C53—H53A	119.8
N2—C3—H3A	123.5	C55—C54—C53	120.2 (2)
N4—C4—N6	114.5 (2)	C55—C54—H54A	119.9
N4—C4—H4A	122.7	C53—C54—H54A	119.9
N6—C4—H4A	122.7	C54—C55—C56	120.0 (2)
N6—C5—N5	113.2 (2)	C54—C55—H55A	120.0
N6—C5—H5A	123.4	C56—C55—H55A	120.0
N5—C5—H5A	123.4	C51—C56—C55	120.1 (2)
C12—C11—C16	118.6 (2)	C51—C56—H56A	120.0
C12—C11—P1	122.82 (16)	C55—C56—H56A	120.0
C16—C11—P1	118.38 (16)	C62—C61—C66	118.5 (2)
C13—C12—C11	119.8 (2)	C62—C61—P2	120.30 (16)
C13—C12—H12A	120.1	C66—C61—P2	121.20 (19)
C11—C12—H12A	120.1	C63—C62—C61	121.0 (2)
C14—C13—C12	121.1 (2)	C63—C62—H62A	119.5
C14—C13—H13A	119.4	C61—C62—H62A	119.5
C12—C13—H13A	119.4	C62—C63—C64	119.8 (2)
C13—C14—C15	119.4 (2)	C62—C63—H63A	120.1
C13—C14—H14A	120.3	C64—C63—H63A	120.1
C15—C14—H14A	120.3	C65—C64—C63	119.9 (2)
C16—C15—C14	119.8 (2)	C65—C64—H64A	120.0
C16—C15—H15A	120.1	C63—C64—H64A	120.0
C14—C15—H15A	120.1	C64—C65—C66	120.4 (2)
C15—C16—C11	121.4 (2)	C64—C65—H65A	119.8
C15—C16—H16A	119.3	C66—C65—H65A	119.8
C11—C16—H16A	119.3	C65—C66—C61	120.4 (2)
C22—C21—C26	118.0 (2)	C65—C66—H66A	119.8
C22—C21—P1	117.78 (16)	C61—C66—H66A	119.8
C26—C21—P1	124.19 (18)	H1B—B1—H2B	113.8 (17)
C23—C22—C21	121.4 (2)	H1B—B1—N2	108.0 (13)
C23—C22—H22A	119.3	H2B—B1—N2	108.9 (12)
C21—C22—H22A	119.3	H1B—B1—N5	108.5 (12)
C22—C23—C24	119.9 (2)	H2B—B1—N5	107.4 (11)
C22—C23—H23A	120.0	N2—B1—N5	110.19 (19)
C24—C23—H23A	120.0	C2S—C1S—H1S	108.5 (12)
C25—C24—C23	119.6 (2)	C2S—C1S—H2S	108.8 (12)
C25—C24—H24A	120.2	H1S—C1S—H2S	109.6 (13)
C23—C24—H24A	120.2	C2S—C1S—H3S	109.8 (12)
C24—C25—C26	120.5 (2)	H1S—C1S—H3S	109.6 (14)
C24—C25—H25A	119.7	H2S—C1S—H3S	110.6 (13)
C26—C25—H25A	119.7	N1S—C2S—C1S	178.4 (3)
C25—C26—C21	120.6 (2)

Experimental details

Crystal data
Chemical formula	[Ru(C₄H₆BN₆)H(C₁₈H₁₅P)₂(CO)]·C₂H₃N
M_r	844.64
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.0733 (1), 11.8032 (3), 20.2609 (6)
α, β, γ (°)	74.438 (11), 89.552 (15), 70.731 (14)
V (Å³)	1965.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.35 × 0.30 × 0.28

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.838, 0.867
No. of measured, independent and observed [I > 2σ(I)] reflections	31908, 8964, 6896
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.079, 0.99
No. of reflections	8964
No. of parameters	521
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.79

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Bruker, 1998).

Selected geometric parameters (Å, º) top

Ru1—H1RU	1.57 (2)	Ru1—N1	2.1771 (17)
Ru1—C1	1.833 (2)	Ru1—P2	2.3588 (6)
Ru1—N4	2.1396 (19)	Ru1—P1	2.3978 (6)

H1RU—Ru1—C1	90.0 (9)	N4—Ru1—P2	95.09 (5)
H1RU—Ru1—N4	87.9 (9)	N1—Ru1—P2	98.90 (5)
C1—Ru1—N4	176.92 (8)	H1RU—Ru1—P1	91.1 (8)
H1RU—Ru1—N1	175.7 (9)	C1—Ru1—P1	91.65 (7)
C1—Ru1—N1	94.31 (8)	N4—Ru1—P1	86.16 (5)
N4—Ru1—N1	87.84 (7)	N1—Ru1—P1	89.15 (5)
H1RU—Ru1—P2	81.0 (8)	P2—Ru1—P1	171.884 (18)
C1—Ru1—P2	86.77 (7)

Acknowledgements

The author thanks Dr Alan J. Lough of the University of Toronto for the structure determination.

References

Bruker (1998). SHELXTL/PC. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huh, S., Kim, Y., Park, S., Park, T.-J. & Jun, M.-J. (1999). Acta Cryst. C55, 850–852. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Huh, S., Park, Y. J., Lough, A. J. & Jun, M.-J. (2000). Acta Cryst. C56, 416–417. CSD CrossRef CAS IUCr Journals Google Scholar
Nonius (1997). KappaCCD Server Software. Version 3.11. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods Enzymol. 276, 307–326. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Youm, K.-T., Huh, S., Kim, Y., Park, S. & Jun, M.-J. (2006). Bull. Korean Chem. Soc. 27, 1521–1522. CAS Google Scholar

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