Polymeric structure of a coproporphyrin I ruthenium(II) complex: a powder diffraction study

Porphyrin complexes of ruthenium are widely used as models for the heme protein system, for modelling naturally occurring iron–porphyrin systems and as catalysts in epoxidation reactions. The structural diversity of ruthenium complexes offers an opportunity to use them in the design of multifunctional supra­molecular assemblies. Coproporphyrins and metallocoproporphyrins are used as sensors in bioassay and the potential use of derivatives as multiparametric sensors for oxygen and H⁺ is one of the main factors driving a growing inter­est in the synthesis of new porphyrin derivatives. In the co­proporphyrin I Ru^II complex catena-poly[[carbonyl­ruthenium(II)]-μ-2,7,12,17-tetra­kis­[2-(eth­oxy­carbon­yl)eth­yl]-3,8,13,18-tetra­methyl­porphyrinato-κ⁵N,N′,N′′,N′′′:O], [Ru(C₄₄H₅₂N₄O₈)(CO)]_n, the Ru^II centre is coordinated by four N atoms in the basal plane, and by axial C (carbonyl ligand) and O (eth­oxy­carbonyl­ethyl arm from a neighbouring complex) atoms. The complex adopts a distorted octa­hedral geometry. Self-assembly of the mol­ecules during crystallization from a methyl­ene chloride–ethanol (1:10 v/v) solution at room temperature gives one-dimensional polymeric chains.

Computing details

Cell refinement: MRIA (Zlokazov & Chernyshev, 1992); program(s) used to solve structure: MRIA (Zlokazov & Chernyshev, 1992) and FOX (Favre-Nicolin & Cerný, 2004); program(s) used to refine structure: MRIA (Zlokazov & Chernyshev, 1992); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

catena-Poly[[carbonylruthenium(II)]-µ-2,7,12,17-tetrakis[2-(ethoxycarbonyl)ethyl]-3,8,13,18-tetramethylporphyrinato-κ⁵N,N',N'',N''':O]

Crystal data

[Ru(C44H52N4O8)(CO)]	F(000) = 3728
Mr = 893.98	Dx = 1.401 Mg m^−3
Monoclinic, C2/c	Synchrotron radiation, λ = 0.399927(2) Å
Hall symbol: -C 2yc	µ = 0.09 mm^−1
a = 39.3876 (19) Å	T = 295 K
b = 9.6153 (8) Å	Particle morphology: no specific habit
c = 29.5299 (16) Å	colorless
β = 130.719 (7)°	cylinder, 15 × 1.0 mm
V = 8476.3 (9) Å^3	Specimen preparation: Prepared at 295 K and 101 kPa
Z = 8

Data collection

ESRF powder diffractometer ID22	Data collection mode: transmission
Radiation source: ID22 bending magnet at ESRF, synchrotron radiation	Scan method: continuous
Si 111 double crystal monochromator	2θmin = 1.000°, 2θmax = 20.000°, 2θstep = 0.002°
Specimen mounting: Specimen was sealed in a 1.0 mm diameter borosilicate glass capillary

Refinement

Refinement on Inet	247 parameters
Least-squares matrix: full with fixed elements per cycle	193 restraints
Rp = 0.031	21 constraints
Rwp = 0.040	H-atom parameters not refined
Rexp = 0.013	Weighting scheme based on measured s.u.'s
RBragg = 0.070	(Δ/σ)max = 0.003
9501 data points	Background function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-Voigt	Preferred orientation correction: none

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ru1	0.88520 (4)	0.5249 (2)	0.82080 (6)	0.0170 (12)*
N1	0.9371 (3)	0.3887 (14)	0.8584 (5)	0.034 (10)*
N2	0.8917 (3)	0.5230 (13)	0.8947 (5)	0.034 (10)*
N3	0.8290 (3)	0.6456 (15)	0.7803 (5)	0.034 (10)*
N4	0.8732 (3)	0.5119 (13)	0.7428 (5)	0.034 (10)*
C1	0.9549 (4)	0.3341 (19)	0.8342 (6)	0.034 (10)*
C2	0.9928 (4)	0.2503 (19)	0.8768 (6)	0.034 (10)*
C3	0.9990 (4)	0.2549 (18)	0.9290 (7)	0.034 (10)*
C4	0.9652 (4)	0.3374 (19)	0.9178 (6)	0.034 (10)*
C5	0.9575 (4)	0.3725 (18)	0.9559 (5)	0.034 (10)*
H5	0.9776	0.3334	0.9938	0.041*
C6	0.9254 (4)	0.4549 (18)	0.9473 (6)	0.034 (10)*
C7	0.9209 (4)	0.4849 (18)	0.9914 (6)	0.034 (10)*
C8	0.8857 (4)	0.5682 (17)	0.9663 (6)	0.034 (10)*
C9	0.8675 (4)	0.5963 (19)	0.9058 (6)	0.034 (10)*
C10	0.8307 (4)	0.6775 (19)	0.8638 (6)	0.034 (10)*
H10	0.8167	0.7226	0.8756	0.041*
C11	0.8129 (4)	0.6974 (17)	0.8053 (6)	0.034 (10)*
C12	0.7734 (4)	0.7848 (19)	0.7630 (6)	0.034 (10)*
C13	0.7672 (4)	0.7845 (18)	0.7121 (6)	0.034 (10)*
C14	0.8005 (4)	0.6945 (18)	0.7212 (6)	0.034 (10)*
C15	0.8070 (4)	0.6615 (19)	0.6821 (5)	0.034 (10)*
H15	0.7866	0.7008	0.6443	0.041*
C16	0.8397 (4)	0.5778 (19)	0.6906 (6)	0.034 (10)*
C17	0.8442 (4)	0.5503 (17)	0.6468 (6)	0.034 (10)*
C18	0.8800 (4)	0.4628 (17)	0.6723 (6)	0.034 (10)*
C19	0.8980 (4)	0.4395 (19)	0.7331 (6)	0.034 (10)*
C20	0.9356 (4)	0.3604 (19)	0.7753 (6)	0.034 (10)*
H20	0.9497	0.3198	0.7628	0.041*
C21	1.0222 (5)	0.1708 (18)	0.8744 (7)	0.034 (10)*
H21A	1.0297	0.0874	0.8978	0.041*
H21B	1.0497	0.2240	0.8954	0.041*
C22	1.0099 (4)	0.126 (2)	0.8183 (6)	0.049 (10)*
H22A	1.0048	0.2078	0.7952	0.059*
H22B	0.9821	0.0744	0.7956	0.059*
C23	1.0462 (4)	0.0347 (18)	0.8273 (7)	0.055 (11)*
C24	1.0564 (5)	−0.214 (2)	0.8123 (6)	0.069 (10)*
H24A	1.0360	−0.2920	0.7966	0.083*
H24B	1.0856	−0.2452	0.8478	0.083*
C25	1.0596 (5)	−0.168 (2)	0.7667 (7)	0.089 (11)*
H25A	1.0699	−0.2447	0.7575	0.134*
H25B	1.0803	−0.0925	0.7823	0.134*
H25C	1.0306	−0.1392	0.7311	0.134*
C26	1.0361 (4)	0.1737 (18)	0.9841 (6)	0.034 (10)*
H26A	1.0538	0.1275	0.9770	0.051*
H26B	1.0233	0.1058	0.9930	0.051*
H26C	1.0547	0.2362	1.0173	0.051*
C27	0.9516 (4)	0.4256 (18)	1.0535 (6)	0.034 (10)*
H27A	0.9472	0.4749	1.0780	0.041*
H27B	0.9825	0.4390	1.0710	0.041*
C28	0.9429 (4)	0.2704 (18)	1.0533 (6)	0.051 (10)*
H28A	0.9447	0.2243	1.0257	0.061*
H28B	0.9669	0.2337	1.0928	0.061*
C29	0.8992 (4)	0.2311 (19)	1.0369 (6)	0.059 (11)*
C30	0.8427 (5)	0.0444 (18)	1.0068 (7)	0.071 (11)*
H30A	0.8262	0.1176	1.0078	0.085*
H30B	0.8528	−0.0222	1.0381	0.085*
C31	0.8128 (4)	−0.0275 (16)	0.9454 (5)	0.091 (12)*
H31A	0.7895	0.0350	0.9158	0.136*
H31B	0.7997	−0.1095	0.9470	0.136*
H31C	0.8306	−0.0529	0.9350	0.136*
C32	0.8667 (4)	0.6283 (19)	0.9920 (6)	0.034 (10)*
H32A	0.8411	0.6845	0.9624	0.051*
H32B	0.8889	0.6848	1.0260	0.051*
H32C	0.8578	0.5545	1.0042	0.051*
C33	0.7508 (4)	0.859 (2)	0.7794 (6)	0.034 (10)*
H33A	0.7311	0.9267	0.7482	0.041*
H33B	0.7734	0.9112	0.8155	0.041*
C34	0.7244 (5)	0.7836 (17)	0.7898 (7)	0.046 (10)*
H34A	0.7200	0.8411	0.8126	0.055*
H34B	0.7402	0.7001	0.8127	0.055*
C35	0.6781 (4)	0.7437 (17)	0.7289 (6)	0.050 (10)*
C36	0.6421 (4)	0.5757 (18)	0.6487 (7)	0.058 (10)*
H36A	0.6347	0.6607	0.6262	0.070*
H36B	0.6569	0.5129	0.6406	0.070*
C37	0.6008 (4)	0.5101 (18)	0.6313 (7)	0.068 (12)*
H37A	0.5807	0.4886	0.5894	0.102*
H37B	0.5865	0.5733	0.6395	0.102*
H37C	0.6086	0.4261	0.6538	0.102*
C38	0.7278 (4)	0.8624 (18)	0.6580 (6)	0.034 (10)*
H38A	0.7279	0.8526	0.6258	0.051*
H38B	0.7300	0.9591	0.6677	0.051*
H38C	0.7004	0.8250	0.6462	0.051*
C39	0.8137 (4)	0.6012 (19)	0.5812 (6)	0.034 (10)*
H39A	0.7997	0.6887	0.5771	0.041*
H39B	0.8313	0.6155	0.5693	0.041*
C40	0.7777 (4)	0.4897 (18)	0.5414 (6)	0.052 (12)*
H40A	0.7921	0.3996	0.5515	0.062*
H40B	0.7576	0.4866	0.5498	0.062*
C41	0.7509 (5)	0.5157 (17)	0.4762 (7)	0.058 (11)*
C42	0.6974 (4)	0.4449 (19)	0.3694 (7)	0.071 (11)*
H42A	0.6946	0.5437	0.3609	0.085*
H42B	0.7114	0.4020	0.3555	0.085*
C43	0.6524 (4)	0.384 (2)	0.3371 (6)	0.094 (11)*
H43A	0.6345	0.3992	0.2950	0.141*
H43B	0.6383	0.4276	0.3504	0.141*
H43C	0.6552	0.2860	0.3449	0.141*
C44	0.8932 (4)	0.4175 (19)	0.6362 (6)	0.034 (10)*
H44A	0.9187	0.3568	0.6600	0.051*
H44B	0.9006	0.4979	0.6249	0.051*
H44C	0.8686	0.3692	0.6010	0.051*
O1	1.0781 (3)	0.0868 (13)	0.8400 (4)	0.058 (7)*
O2	1.0411 (3)	−0.1050 (14)	0.8286 (4)	0.063 (7)*
O3	0.8775 (3)	0.3143 (12)	1.0409 (4)	0.054 (7)*
O4	0.8818 (3)	0.1038 (13)	1.0157 (4)	0.058 (7)*
O5	0.6509 (3)	0.8273 (12)	0.7038 (4)	0.042 (6)*
O6	0.6724 (3)	0.6071 (13)	0.7148 (4)	0.053 (6)*
O7	0.7559 (3)	0.6281 (14)	0.4631 (4)	0.054 (6)*
O8	0.7260 (3)	0.4236 (13)	0.4346 (4)	0.060 (7)*
O9	0.9432 (3)	0.7812 (12)	0.8590 (4)	0.074 (7)*
C45	0.9192 (5)	0.6859 (19)	0.8412 (6)	0.074 (10)*

Geometric parameters (Å, º)

Ru1—C45	1.871 (19)	C25—H25C	0.9600
Ru1—N2	2.025 (17)	C26—H26A	0.9601
Ru1—N4	2.031 (16)	C26—H26B	0.9599
Ru1—N1	2.041 (12)	C26—H26C	0.9600
Ru1—N3	2.055 (12)	C27—C28	1.53 (2)
Ru1—O5^i	2.194 (12)	C27—H27A	0.9700
N1—C1	1.39 (3)	C27—H27B	0.9700
N1—C4	1.418 (18)	C28—C29	1.50 (3)
N2—C6	1.383 (17)	C28—H28A	0.9700
N2—C9	1.39 (3)	C28—H28B	0.9700
N3—C11	1.34 (3)	C29—O3	1.23 (2)
N3—C14	1.404 (18)	C29—O4	1.34 (2)
N4—C16	1.366 (16)	C30—O4	1.50 (2)
N4—C19	1.37 (3)	C30—C31	1.54 (2)
C1—C20	1.39 (2)	C30—H30A	0.9701
C1—C2	1.418 (19)	C30—H30B	0.9699
C2—C3	1.40 (3)	C31—H31A	0.9600
C2—C21	1.43 (3)	C31—H31B	0.9600
C3—C4	1.39 (3)	C31—H31C	0.9600
C3—C26	1.513 (18)	C32—H32A	0.9600
C4—C5	1.38 (3)	C32—H32B	0.9600
C5—C6	1.37 (2)	C32—H32C	0.9603
C5—H5	0.9300	C33—C34	1.46 (3)
C6—C7	1.45 (3)	C33—H33A	0.9699
C7—C8	1.33 (2)	C33—H33B	0.9700
C7—C27	1.50 (2)	C34—C35	1.558 (16)
C8—C9	1.45 (2)	C34—H34A	0.9702
C8—C32	1.49 (3)	C34—H34B	0.9700
C9—C10	1.380 (19)	C35—O5	1.143 (17)
C10—C11	1.39 (2)	C35—O6	1.35 (2)
C10—H10	0.9299	C36—C37	1.49 (3)
C11—C12	1.467 (19)	C36—O6	1.512 (19)
C12—C13	1.36 (3)	C36—H36A	0.9700
C12—C33	1.45 (3)	C36—H36B	0.9701
C13—C14	1.44 (3)	C37—H37A	0.9601
C13—C38	1.512 (17)	C37—H37B	0.9599
C14—C15	1.37 (3)	C37—H37C	0.9602
C15—C16	1.40 (3)	C38—H38A	0.9600
C15—H15	0.9300	C38—H38B	0.9599
C16—C17	1.44 (3)	C38—H38C	0.9601
C17—C18	1.37 (2)	C39—C40	1.54 (2)
C17—C39	1.55 (2)	C39—H39A	0.9701
C18—C19	1.45 (3)	C39—H39B	0.9699
C18—C44	1.52 (3)	C40—C41	1.49 (2)
C19—C20	1.385 (18)	C40—H40A	0.9701
C20—H20	0.9299	C40—H40B	0.9699
C21—C22	1.45 (3)	C41—O7	1.21 (2)
C21—H21A	0.9699	C41—O8	1.297 (18)
C21—H21B	0.9701	C42—C43	1.48 (2)
C22—C23	1.55 (3)	C42—O8	1.48 (2)
C22—H22A	0.9700	C42—H42A	0.9700
C22—H22B	0.9700	C42—H42B	0.9699
C23—O1	1.16 (2)	C43—H43A	0.9601
C23—O2	1.36 (2)	C43—H43B	0.9599
C24—O2	1.44 (3)	C43—H43C	0.9600
C24—C25	1.50 (3)	C44—H44A	0.9600
C24—H24A	0.9700	C44—H44B	0.9600
C24—H24B	0.9700	C44—H44C	0.9600
C25—H25A	0.9601	O5—Ru1^ii	2.194 (11)
C25—H25B	0.9599	O9—C45	1.17 (2)
C45—Ru1—N2	95.7 (7)	H25B—C25—H25C	109.5
C45—Ru1—N4	90.2 (7)	C3—C26—H26A	109.5
N2—Ru1—N4	173.8 (5)	C3—C26—H26B	109.5
C45—Ru1—N1	95.9 (7)	H26A—C26—H26B	109.5
N2—Ru1—N1	91.7 (6)	C3—C26—H26C	109.5
N4—Ru1—N1	89.3 (5)	H26A—C26—H26C	109.5
C45—Ru1—N3	89.6 (7)	H26B—C26—H26C	109.5
N2—Ru1—N3	87.9 (6)	C7—C27—C28	111.4 (12)
N4—Ru1—N3	90.5 (5)	C7—C27—H27A	109.3
N1—Ru1—N3	174.5 (5)	C28—C27—H27A	109.3
C45—Ru1—O5^i	175.2 (8)	C7—C27—H27B	109.3
N2—Ru1—O5^i	87.0 (5)	C28—C27—H27B	109.3
N4—Ru1—O5^i	87.1 (5)	H27A—C27—H27B	108.0
N1—Ru1—O5^i	80.0 (5)	C29—C28—C27	117.0 (15)
N3—Ru1—O5^i	94.4 (5)	C29—C28—H28A	108.1
C1—N1—C4	104.8 (12)	C27—C28—H28A	108.0
C1—N1—Ru1	128.7 (10)	C29—C28—H28B	108.1
C4—N1—Ru1	126.3 (13)	C27—C28—H28B	108.0
C6—N2—C9	106.2 (15)	H28A—C28—H28B	107.3
C6—N2—Ru1	124.7 (14)	O3—C29—O4	117.5 (16)
C9—N2—Ru1	128.9 (9)	O3—C29—C28	121.8 (16)
C11—N3—C14	106.1 (13)	O4—C29—C28	120.6 (17)
C11—N3—Ru1	127.2 (9)	O4—C30—C31	106.7 (17)
C14—N3—Ru1	126.6 (13)	O4—C30—H30A	110.4
C16—N4—C19	107.1 (15)	C31—C30—H30A	110.4
C16—N4—Ru1	126.2 (13)	O4—C30—H30B	110.4
C19—N4—Ru1	126.6 (8)	C31—C30—H30B	110.4
N1—C1—C20	121.7 (13)	H30A—C30—H30B	108.6
N1—C1—C2	110.5 (15)	C30—C31—H31A	109.5
C20—C1—C2	127.7 (19)	C30—C31—H31B	109.5
C3—C2—C1	106.7 (17)	H31A—C31—H31B	109.5
C3—C2—C21	120.6 (13)	C30—C31—H31C	109.5
C1—C2—C21	132.8 (18)	H31A—C31—H31C	109.5
C4—C3—C2	107.7 (13)	H31B—C31—H31C	109.5
C4—C3—C26	130.7 (19)	C8—C32—H32A	109.5
C2—C3—C26	121.5 (17)	C8—C32—H32B	109.5
C5—C4—C3	128.9 (13)	H32A—C32—H32B	109.5
C5—C4—N1	120.8 (14)	C8—C32—H32C	109.5
C3—C4—N1	110.2 (17)	H32A—C32—H32C	109.4
C6—C5—C4	131.0 (13)	H32B—C32—H32C	109.4
C6—C5—H5	114.5	C12—C33—C34	120.2 (18)
C4—C5—H5	114.5	C12—C33—H33A	107.3
C5—C6—N2	125.2 (18)	C34—C33—H33A	107.3
C5—C6—C7	125.9 (13)	C12—C33—H33B	107.3
N2—C6—C7	108.9 (15)	C34—C33—H33B	107.3
C8—C7—C6	108.2 (15)	H33A—C33—H33B	106.9
C8—C7—C27	129 (2)	C33—C34—C35	109.8 (15)
C6—C7—C27	123.2 (15)	C33—C34—H34A	109.7
C7—C8—C9	107.2 (19)	C35—C34—H34A	109.7
C7—C8—C32	129.6 (16)	C33—C34—H34B	109.7
C9—C8—C32	123.2 (13)	C35—C34—H34B	109.7
C10—C9—N2	123.8 (16)	H34A—C34—H34B	108.2
C10—C9—C8	126.7 (18)	O5—C35—O6	125.9 (11)
N2—C9—C8	109.4 (13)	O5—C35—C34	118.1 (14)
C9—C10—C11	125.3 (19)	O6—C35—C34	115.4 (11)
C9—C10—H10	117.4	C37—C36—O6	107.1 (17)
C11—C10—H10	117.4	C37—C36—H36A	110.3
N3—C11—C10	126.5 (14)	O6—C36—H36A	110.3
N3—C11—C12	111.3 (14)	C37—C36—H36B	110.3
C10—C11—C12	122.1 (18)	O6—C36—H36B	110.3
C13—C12—C33	131.7 (13)	H36A—C36—H36B	108.5
C13—C12—C11	105.5 (16)	C36—C37—H37A	109.5
C33—C12—C11	122.6 (15)	C36—C37—H37B	109.5
C12—C13—C14	108.1 (13)	H37A—C37—H37B	109.5
C12—C13—C38	119.2 (17)	C36—C37—H37C	109.5
C14—C13—C38	132.5 (17)	H37A—C37—H37C	109.5
C15—C14—N3	122.1 (15)	H37B—C37—H37C	109.5
C15—C14—C13	128.9 (13)	C13—C38—H38A	109.5
N3—C14—C13	109.0 (17)	C13—C38—H38B	109.5
C14—C15—C16	129.7 (13)	H38A—C38—H38B	109.5
C14—C15—H15	115.2	C13—C38—H38C	109.5
C16—C15—H15	115.2	H38A—C38—H38C	109.5
N4—C16—C15	124.7 (18)	H38B—C38—H38C	109.5
N4—C16—C17	109.5 (15)	C40—C39—C17	108.2 (14)
C15—C16—C17	125.7 (13)	C40—C39—H39A	110.1
C18—C17—C16	107.7 (14)	C17—C39—H39A	110.1
C18—C17—C39	124.2 (19)	C40—C39—H39B	110.1
C16—C17—C39	128.0 (15)	C17—C39—H39B	110.1
C17—C18—C19	105.7 (18)	H39A—C39—H39B	108.4
C17—C18—C44	119.3 (15)	C41—C40—C39	113.1 (15)
C19—C18—C44	134.9 (13)	C41—C40—H40A	109.0
N4—C19—C20	125.4 (17)	C39—C40—H40A	109.0
N4—C19—C18	109.8 (12)	C41—C40—H40B	109.0
C20—C19—C18	124.7 (19)	C39—C40—H40B	109.0
C19—C20—C1	128.0 (19)	H40A—C40—H40B	107.8
C19—C20—H20	116.0	O7—C41—O8	119.2 (16)
C1—C20—H20	116.0	O7—C41—C40	115.9 (13)
C2—C21—C22	122.4 (11)	O8—C41—C40	124.6 (16)
C2—C21—H21A	106.7	C43—C42—O8	111.1 (17)
C22—C21—H21A	106.7	C43—C42—H42A	109.4
C2—C21—H21B	106.7	O8—C42—H42A	109.4
C22—C21—H21B	106.7	C43—C42—H42B	109.4
H21A—C21—H21B	106.6	O8—C42—H42B	109.4
C21—C22—C23	112.8 (11)	H42A—C42—H42B	108.0
C21—C22—H22A	109.0	C42—C43—H43A	109.5
C23—C22—H22A	109.0	C42—C43—H43B	109.5
C21—C22—H22B	109.0	H43A—C43—H43B	109.5
C23—C22—H22B	109.0	C42—C43—H43C	109.5
H22A—C22—H22B	107.8	H43A—C43—H43C	109.5
O1—C23—O2	124.3 (16)	H43B—C43—H43C	109.5
O1—C23—C22	119.5 (16)	C18—C44—H44A	109.5
O2—C23—C22	115.4 (16)	C18—C44—H44B	109.5
O2—C24—C25	112.9 (15)	H44A—C44—H44B	109.5
O2—C24—H24A	109.0	C18—C44—H44C	109.5
C25—C24—H24A	109.0	H44A—C44—H44C	109.5
O2—C24—H24B	109.0	H44B—C44—H44C	109.5
C25—C24—H24B	109.0	C23—O2—C24	127.3 (17)
H24A—C24—H24B	107.8	C29—O4—C30	125.7 (15)
C24—C25—H25A	109.5	C35—O5—Ru1^ii	162.6 (10)
C24—C25—H25B	109.5	C35—O6—C36	115.1 (12)
H25A—C25—H25B	109.5	C41—O8—C42	127.0 (14)
C24—C25—H25C	109.5	O9—C45—Ru1	173.9 (13)
H25A—C25—H25C	109.5

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25C···O2^iii	0.96	2.17	3.08 (2)	157
C37—H37C···O9^i	0.96	2.29	2.93 (2)	123
C39—H39A···O7^iv	0.97	2.43	3.37 (2)	161
C39—H39B···O3^v	0.97	2.54	3.51 (2)	173
C43—H43B···O1^vi	0.96	2.19	3.00 (2)	141
C44—H44A···O1^iii	0.96	2.60	3.29 (2)	129

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (iii) −x+2, y, −z+3/2; (iv) −x+3/2, −y+3/2, −z+1; (v) x, −y+1, z−1/2; (vi) x−1/2, −y+1/2, z−1/2.