Ruthenium(II)–carbonyl complexes containing two N-monodentate 1,8-naphthyridine ligands: active catalysis in transfer hydrogenation reactions

The reaction of 2-amino­nicotinaldehyde with 2- or 4-meth­oxy­aceto­phenone in basic media leads to the new ligands 2-(4-meth­oxy­phen­yl)-1,8-naphthyridine and 2-(2-meth­oxy­phen­yl)-1,8-naphthyridine, respectively, in high yield. The reaction of these naphthyridine derivatives with [RuCl₂(CO)₂]_n leads to the respective complexes cis-di­carbonyl­dichlorido­bis­[2-(4-meth­oxy­phen­yl)-1,8-naph­thyridine-κN⁸]ruthenium(II) and cis-di­car­bonyl­dichlorido­bis­[2-(2-meth­oxy­phen­yl)-1,8-naphthyridine-κN⁸]ruthenium(II), both [RuCl₂(C₁₅H₁₂N₂O)₂(CO)₂], in good yield. Both ruthenium(II) complexes display a slightly distorted octa­hedron with two cis carbonyl, two cis chloride and two cis naphthyridine ligands, the latter coordinated in a monodentate fashion through the N atom in the 8-position. Both complexes exhibit a moderate catalytic activity in the hydrogen-transfer reaction from propan-2-ol to aceto­phenone in the presence of a base, with 100% selectivity.

Computing details

For both structures, data collection: SMART (Bruker, 2012); cell refinement: SMART (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Bruker, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

cis-Dicarbonyldichloridobis[2-(4-methoxyphenyl)-1,8-naphthyridine-κN⁸]ruthenium(II) (Ru_A)

Crystal data

[RuCl2(C15H12N2O)2(CO)2]	Z = 2
Mr = 700.52	F(000) = 708
Triclinic, P1	Dx = 1.537 Mg m^−3
a = 10.8018 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6708 (16) Å	Cell parameters from 999 reflections
c = 14.248 (2) Å	θ = 4.5–46.9°
α = 93.707 (2)°	µ = 0.74 mm^−1
β = 105.555 (2)°	T = 296 K
γ = 116.417 (2)°	Plate, yellow
V = 1514.1 (4) Å^3	0.27 × 0.26 × 0.05 mm

Data collection

Bruker SMART CCD area detector diffractometer	4861 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	Rint = 0.021
phi and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2012)	h = −13→13
Tmin = 0.819, Tmax = 0.964	k = −14→14
11949 measured reflections	l = −17→17
5886 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.1027P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5886 reflections	Δρmax = 0.76 e Å^−3
390 parameters	Δρmin = −0.22 e Å^−3

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.9012 (0.0050) x - 10.8797 (0.0039) y + 3.1820 (0.0121) z = 1.3347 (0.0070)

* 0.0561 (0.0020) N1A * 0.0169 (0.0024) C1A * -0.0659 (0.0025) C2A * -0.0310 (0.0025) C3A * 0.0284 (0.0026) C14A * 0.0588 (0.0027) C4A * 0.0202 (0.0026) C5A * -0.0911 (0.0021) C12A * 0.0077 (0.0024) C13A

Rms deviation of fitted atoms = 0.0492

- 5.2857 (0.0138) x + 11.5034 (0.0032) y + 1.4914 (0.0197) z = 2.0137 (0.0126)

Angle to previous plane (with approximate esd) = 26.938 ( 0.100 )

* 0.0042 (0.0023) C11A * -0.0001 (0.0024) C6A * -0.0021 (0.0026) C7A * 0.0003 (0.0025) C8A * 0.0039 (0.0026) C9A * -0.0063 (0.0026) C10A

Rms deviation of fitted atoms = 0.0036

- 0.5195 (0.0100) x + 10.0547 (0.0055) y + 2.0390 (0.0083) z = 1.5842 (0.0058)

Angle to previous plane (with approximate esd) = 28.060 ( 0.083 )

* 0.0309 (0.0019) N1B * -0.0011 (0.0023) C1B * -0.0301 (0.0024) C2B * -0.0054 (0.0024) C3B * 0.0129 (0.0026) C14B * 0.0190 (0.0026) C4B * 0.0103 (0.0026) C5B * -0.0404 (0.0021) C12B * 0.0039 (0.0024) C13B

Rms deviation of fitted atoms = 0.0215

- 1.4570 (0.0156) x + 10.6670 (0.0066) y + 1.3367 (0.0212) z = 1.1428 (0.0074)

Angle to previous plane (with approximate esd) = 6.588 ( 0.131 )

* -0.0003 (0.0023) C11B * 0.0020 (0.0026) C6B * -0.0024 (0.0027) C7B * 0.0010 (0.0026) C8B * 0.0008 (0.0025) C9B * -0.0011 (0.0024) C10B

Rms deviation of fitted atoms = 0.0015

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

	x	y	z	Uiso*/Ueq
Ru1	0.34638 (2)	0.15266 (2)	0.27576 (2)	0.04391 (10)
C1	0.2245 (3)	0.0235 (3)	0.1584 (3)	0.0568 (8)
C2	0.3888 (3)	0.2831 (3)	0.2017 (2)	0.0483 (7)
Cl1	0.14218 (8)	0.18405 (9)	0.27848 (6)	0.0595 (2)
Cl2	0.27212 (9)	−0.01997 (8)	0.36903 (7)	0.0635 (2)
O1	0.1472 (3)	−0.0529 (3)	0.0876 (2)	0.0893 (9)
O2	0.3996 (2)	0.3603 (2)	0.15678 (18)	0.0679 (6)
C1A	0.4212 (3)	0.2857 (3)	0.4881 (2)	0.0512 (7)
H1A	0.3261	0.2189	0.4754	0.061*
C2A	0.4950 (4)	0.3676 (3)	0.5821 (2)	0.0562 (8)
H2A	0.4471	0.3582	0.6287	0.067*
C3A	0.6368 (4)	0.4614 (3)	0.6060 (2)	0.0577 (8)
H3A	0.6888	0.5143	0.6696	0.069*
C4A	0.8492 (4)	0.5708 (3)	0.5479 (2)	0.0593 (8)
H4A	0.9090	0.6229	0.6111	0.071*
C5A	0.9019 (3)	0.5854 (3)	0.4713 (2)	0.0579 (8)
H5A	0.9991	0.6459	0.4818	0.069*
C6A	1.0098 (3)	0.6003 (3)	0.2985 (3)	0.0613 (9)
H6A	1.0797	0.6242	0.3612	0.074*
C7A	1.0536 (4)	0.6309 (4)	0.2168 (3)	0.0673 (10)
H7A	1.1531	0.6752	0.2252	0.081*
C8A	0.9530 (4)	0.5969 (3)	0.1236 (3)	0.0588 (8)
C9A	0.8047 (4)	0.5308 (3)	0.1107 (3)	0.0676 (10)
H9A	0.7351	0.5078	0.0480	0.081*
C10A	0.7622 (3)	0.4997 (3)	0.1929 (2)	0.0637 (9)
H10A	0.6625	0.4538	0.1837	0.076*
C11A	0.8598 (3)	0.5332 (3)	0.2876 (2)	0.0493 (7)
C12A	0.8088 (3)	0.5083 (3)	0.3745 (2)	0.0471 (7)
C13A	0.6209 (3)	0.3978 (3)	0.4352 (2)	0.0429 (6)
C14A	0.7029 (3)	0.4762 (3)	0.5319 (2)	0.0482 (7)
C15A	0.9070 (4)	0.6131 (5)	−0.0467 (3)	0.0978 (15)
H15A	0.8399	0.5210	−0.0699	0.147*
H15B	0.9588	0.6439	−0.0928	0.147*
H15C	0.8535	0.6593	−0.0419	0.147*
C1B	0.6010 (3)	0.1132 (3)	0.3711 (2)	0.0483 (7)
H1B	0.5567	0.1007	0.4200	0.058*
C2B	0.7346 (3)	0.1129 (3)	0.3928 (2)	0.0500 (7)
H2B	0.7770	0.0991	0.4540	0.060*
C3B	0.8014 (3)	0.1330 (3)	0.3224 (2)	0.0487 (7)
H3B	0.8917	0.1355	0.3356	0.058*
C4B	0.7922 (3)	0.1695 (3)	0.1523 (2)	0.0558 (8)
H4B	0.8826	0.1733	0.1613	0.067*
C5B	0.7186 (3)	0.1826 (3)	0.0649 (2)	0.0570 (8)
H5B	0.7590	0.1976	0.0140	0.068*
C6B	0.5443 (3)	0.1976 (3)	−0.1269 (2)	0.0636 (9)
H6B	0.6381	0.2097	−0.1183	0.076*
C7B	0.4603 (4)	0.1972 (4)	−0.2189 (3)	0.0713 (10)
H7B	0.4975	0.2084	−0.2714	0.086*
C8B	0.3209 (3)	0.1803 (3)	−0.2333 (2)	0.0584 (8)
C9B	0.2666 (3)	0.1631 (3)	−0.1558 (2)	0.0611 (9)
H9B	0.1730	0.1516	−0.1647	0.073*
C10B	0.3521 (3)	0.1632 (3)	−0.0643 (2)	0.0591 (8)
H10B	0.3141	0.1513	−0.0122	0.071*
C11B	0.4925 (3)	0.1803 (3)	−0.0470 (2)	0.0479 (7)
C12B	0.5787 (3)	0.1732 (3)	0.0506 (2)	0.0455 (7)
C13B	0.5956 (3)	0.1458 (3)	0.2115 (2)	0.0399 (6)
C14B	0.7333 (3)	0.1501 (3)	0.2300 (2)	0.0439 (7)
C15B	0.0925 (4)	0.1389 (4)	−0.3513 (3)	0.0735 (10)
H15D	0.0427	0.0558	−0.3345	0.110*
H15E	0.0503	0.1321	−0.4212	0.110*
H15F	0.0827	0.2038	−0.3137	0.110*
N1A	0.4788 (2)	0.2973 (2)	0.41504 (17)	0.0444 (6)
N2A	0.6717 (2)	0.4155 (2)	0.35779 (17)	0.0447 (6)
N1B	0.5330 (2)	0.1304 (2)	0.28494 (16)	0.0401 (5)
N2B	0.5205 (2)	0.1561 (2)	0.12268 (17)	0.0432 (5)
O3A	1.0086 (3)	0.6354 (3)	0.04856 (18)	0.0750 (7)
O3B	0.2445 (2)	0.1762 (3)	−0.32803 (18)	0.0791 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.03213 (14)	0.05153 (16)	0.05271 (16)	0.02061 (11)	0.01980 (11)	0.01231 (11)
C1	0.0428 (18)	0.064 (2)	0.070 (2)	0.0255 (17)	0.0274 (17)	0.0147 (18)
C2	0.0343 (15)	0.061 (2)	0.0535 (18)	0.0272 (15)	0.0132 (13)	0.0102 (16)
Cl1	0.0389 (4)	0.0765 (5)	0.0747 (5)	0.0333 (4)	0.0263 (4)	0.0163 (4)
Cl2	0.0516 (5)	0.0640 (5)	0.0789 (6)	0.0235 (4)	0.0326 (4)	0.0275 (4)
O1	0.0672 (17)	0.0851 (19)	0.0809 (18)	0.0162 (15)	0.0170 (14)	−0.0139 (16)
O2	0.0550 (14)	0.0795 (17)	0.0804 (16)	0.0373 (13)	0.0258 (12)	0.0357 (14)
C1A	0.0469 (17)	0.0600 (19)	0.0585 (19)	0.0285 (15)	0.0283 (15)	0.0204 (16)
C2A	0.069 (2)	0.068 (2)	0.0544 (18)	0.0418 (19)	0.0362 (17)	0.0251 (17)
C3A	0.067 (2)	0.062 (2)	0.0486 (17)	0.0351 (18)	0.0203 (16)	0.0111 (16)
C4A	0.0523 (19)	0.060 (2)	0.0564 (19)	0.0232 (17)	0.0129 (16)	0.0026 (16)
C5A	0.0436 (17)	0.0540 (19)	0.067 (2)	0.0165 (15)	0.0180 (16)	0.0064 (16)
C6A	0.0447 (18)	0.070 (2)	0.068 (2)	0.0247 (17)	0.0222 (16)	0.0186 (18)
C7A	0.0430 (18)	0.077 (2)	0.086 (3)	0.0240 (18)	0.0336 (19)	0.030 (2)
C8A	0.0507 (19)	0.058 (2)	0.075 (2)	0.0237 (16)	0.0334 (18)	0.0209 (18)
C9A	0.050 (2)	0.077 (2)	0.061 (2)	0.0167 (18)	0.0216 (17)	0.0160 (18)
C10A	0.0412 (18)	0.068 (2)	0.066 (2)	0.0099 (16)	0.0232 (16)	0.0114 (18)
C11A	0.0420 (16)	0.0411 (16)	0.0623 (19)	0.0154 (14)	0.0223 (15)	0.0089 (14)
C12A	0.0420 (16)	0.0448 (17)	0.0579 (18)	0.0216 (14)	0.0202 (14)	0.0106 (14)
C13A	0.0416 (15)	0.0462 (16)	0.0507 (16)	0.0274 (14)	0.0181 (13)	0.0128 (13)
C14A	0.0507 (18)	0.0512 (18)	0.0523 (17)	0.0307 (15)	0.0196 (14)	0.0135 (14)
C15A	0.073 (3)	0.141 (4)	0.081 (3)	0.041 (3)	0.039 (2)	0.056 (3)
C1B	0.0456 (17)	0.0522 (18)	0.0543 (17)	0.0249 (15)	0.0241 (14)	0.0151 (15)
C2B	0.0423 (16)	0.0587 (19)	0.0519 (17)	0.0277 (15)	0.0132 (14)	0.0151 (15)
C3B	0.0344 (15)	0.0553 (18)	0.0593 (18)	0.0236 (14)	0.0161 (14)	0.0131 (15)
C4B	0.0390 (16)	0.077 (2)	0.0642 (19)	0.0342 (16)	0.0236 (15)	0.0210 (17)
C5B	0.0436 (17)	0.085 (2)	0.0563 (18)	0.0356 (17)	0.0263 (15)	0.0218 (17)
C6B	0.0405 (17)	0.083 (2)	0.071 (2)	0.0263 (17)	0.0253 (16)	0.0341 (19)
C7B	0.051 (2)	0.103 (3)	0.066 (2)	0.034 (2)	0.0280 (17)	0.045 (2)
C8B	0.0450 (18)	0.064 (2)	0.064 (2)	0.0234 (16)	0.0170 (16)	0.0304 (17)
C9B	0.0412 (17)	0.075 (2)	0.070 (2)	0.0310 (17)	0.0161 (16)	0.0193 (18)
C10B	0.0456 (18)	0.082 (2)	0.0573 (19)	0.0342 (17)	0.0218 (15)	0.0187 (17)
C11B	0.0396 (16)	0.0541 (18)	0.0521 (17)	0.0221 (14)	0.0180 (14)	0.0162 (14)
C12B	0.0343 (15)	0.0475 (17)	0.0544 (17)	0.0180 (13)	0.0173 (13)	0.0104 (14)
C13B	0.0309 (14)	0.0391 (15)	0.0494 (16)	0.0161 (12)	0.0150 (12)	0.0061 (13)
C14B	0.0328 (14)	0.0477 (17)	0.0531 (17)	0.0207 (13)	0.0152 (13)	0.0088 (13)
C15B	0.049 (2)	0.085 (3)	0.084 (3)	0.0334 (19)	0.0133 (18)	0.032 (2)
N1A	0.0392 (13)	0.0518 (14)	0.0502 (14)	0.0245 (12)	0.0208 (11)	0.0170 (12)
N2A	0.0398 (13)	0.0461 (14)	0.0520 (14)	0.0201 (11)	0.0217 (11)	0.0111 (11)
N1B	0.0308 (11)	0.0446 (13)	0.0454 (13)	0.0172 (10)	0.0149 (10)	0.0107 (11)
N2B	0.0322 (12)	0.0485 (14)	0.0510 (14)	0.0197 (11)	0.0164 (11)	0.0107 (11)
O3A	0.0579 (15)	0.0945 (18)	0.0795 (16)	0.0291 (13)	0.0409 (13)	0.0427 (15)
O3B	0.0504 (14)	0.110 (2)	0.0777 (16)	0.0349 (14)	0.0209 (12)	0.0511 (15)

Geometric parameters (Å, º)

Ru1—C2	1.867 (3)	C15A—O3A	1.420 (4)
Ru1—C1	1.879 (4)	C15A—H15A	0.9600
Ru1—N1B	2.116 (2)	C15A—H15B	0.9600
Ru1—N1A	2.175 (2)	C15A—H15C	0.9600
Ru1—Cl1	2.4008 (8)	C1B—N1B	1.329 (3)
Ru1—Cl2	2.4389 (9)	C1B—C2B	1.395 (4)
C1—O1	1.131 (4)	C1B—H1B	0.9300
C2—O2	1.121 (4)	C2B—C3B	1.359 (4)
C1A—N1A	1.335 (3)	C2B—H2B	0.9300
C1A—C2A	1.387 (4)	C3B—C14B	1.400 (4)
C1A—H1A	0.9300	C3B—H3B	0.9300
C2A—C3A	1.357 (4)	C4B—C5B	1.345 (4)
C2A—H2A	0.9300	C4B—C14B	1.401 (4)
C3A—C14A	1.405 (4)	C4B—H4B	0.9300
C3A—H3A	0.9300	C5B—C12B	1.422 (4)
C4A—C5A	1.348 (4)	C5B—H5B	0.9300
C4A—C14A	1.410 (4)	C6B—C7B	1.378 (4)
C4A—H4A	0.9300	C6B—C11B	1.386 (4)
C5A—C12A	1.418 (4)	C6B—H6B	0.9300
C5A—H5A	0.9300	C7B—C8B	1.384 (4)
C6A—C7A	1.381 (4)	C7B—H7B	0.9300
C6A—C11A	1.407 (4)	C8B—O3B	1.366 (4)
C6A—H6A	0.9300	C8B—C9B	1.369 (4)
C7A—C8A	1.370 (5)	C9B—C10B	1.380 (4)
C7A—H7A	0.9300	C9B—H9B	0.9300
C8A—O3A	1.369 (4)	C10B—C11B	1.388 (4)
C8A—C9A	1.385 (4)	C10B—H10B	0.9300
C9A—C10A	1.382 (4)	C11B—C12B	1.482 (4)
C9A—H9A	0.9300	C12B—N2B	1.322 (3)
C10A—C11A	1.373 (4)	C13B—N2B	1.352 (3)
C10A—H10A	0.9300	C13B—N1B	1.371 (3)
C11A—C12A	1.481 (4)	C13B—C14B	1.417 (4)
C12A—N2A	1.332 (3)	C15B—O3B	1.430 (4)
C13A—N2A	1.347 (3)	C15B—H15D	0.9600
C13A—N1A	1.390 (3)	C15B—H15E	0.9600
C13A—C14A	1.407 (4)	C15B—H15F	0.9600
C2—Ru1—C1	90.63 (14)	O3A—C15A—H15C	109.5
C2—Ru1—N1B	95.79 (10)	H15A—C15A—H15C	109.5
C1—Ru1—N1B	94.98 (11)	H15B—C15A—H15C	109.5
C2—Ru1—N1A	91.44 (11)	N1B—C1B—C2B	124.1 (3)
C1—Ru1—N1A	177.08 (11)	N1B—C1B—H1B	117.9
N1B—Ru1—N1A	86.86 (8)	C2B—C1B—H1B	117.9
C2—Ru1—Cl1	85.94 (9)	C3B—C2B—C1B	118.4 (3)
C1—Ru1—Cl1	88.88 (9)	C3B—C2B—H2B	120.8
N1B—Ru1—Cl1	175.75 (6)	C1B—C2B—H2B	120.8
N1A—Ru1—Cl1	89.23 (6)	C2B—C3B—C14B	119.6 (3)
C2—Ru1—Cl2	175.65 (8)	C2B—C3B—H3B	120.2
C1—Ru1—Cl2	87.83 (10)	C14B—C3B—H3B	120.2
N1B—Ru1—Cl2	88.40 (6)	C5B—C4B—C14B	120.3 (3)
N1A—Ru1—Cl2	89.96 (6)	C5B—C4B—H4B	119.9
Cl1—Ru1—Cl2	89.96 (3)	C14B—C4B—H4B	119.9
O1—C1—Ru1	177.3 (3)	C4B—C5B—C12B	119.7 (3)
O2—C2—Ru1	172.3 (3)	C4B—C5B—H5B	120.2
N1A—C1A—C2A	123.8 (3)	C12B—C5B—H5B	120.2
N1A—C1A—H1A	118.1	C7B—C6B—C11B	121.7 (3)
C2A—C1A—H1A	118.1	C7B—C6B—H6B	119.1
C3A—C2A—C1A	120.2 (3)	C11B—C6B—H6B	119.1
C3A—C2A—H2A	119.9	C6B—C7B—C8B	120.1 (3)
C1A—C2A—H2A	119.9	C6B—C7B—H7B	119.9
C2A—C3A—C14A	118.1 (3)	C8B—C7B—H7B	119.9
C2A—C3A—H3A	121.0	O3B—C8B—C9B	124.7 (3)
C14A—C3A—H3A	121.0	O3B—C8B—C7B	115.6 (3)
C5A—C4A—C14A	119.7 (3)	C9B—C8B—C7B	119.6 (3)
C5A—C4A—H4A	120.1	C8B—C9B—C10B	119.4 (3)
C14A—C4A—H4A	120.1	C8B—C9B—H9B	120.3
C4A—C5A—C12A	119.8 (3)	C10B—C9B—H9B	120.3
C4A—C5A—H5A	120.1	C9B—C10B—C11B	122.6 (3)
C12A—C5A—H5A	120.1	C9B—C10B—H10B	118.7
C7A—C6A—C11A	120.4 (3)	C11B—C10B—H10B	118.7
C7A—C6A—H6A	119.8	C6B—C11B—C10B	116.5 (3)
C11A—C6A—H6A	119.8	C6B—C11B—C12B	122.2 (3)
C8A—C7A—C6A	121.0 (3)	C10B—C11B—C12B	121.3 (3)
C8A—C7A—H7A	119.5	N2B—C12B—C5B	121.6 (3)
C6A—C7A—H7A	119.5	N2B—C12B—C11B	118.0 (2)
O3A—C8A—C7A	116.1 (3)	C5B—C12B—C11B	120.4 (3)
O3A—C8A—C9A	124.1 (3)	N2B—C13B—N1B	117.3 (2)
C7A—C8A—C9A	119.7 (3)	N2B—C13B—C14B	122.5 (2)
C10A—C9A—C8A	118.7 (3)	N1B—C13B—C14B	120.1 (2)
C10A—C9A—H9A	120.7	C3B—C14B—C4B	123.8 (3)
C8A—C9A—H9A	120.7	C3B—C14B—C13B	119.2 (3)
C11A—C10A—C9A	123.2 (3)	C4B—C14B—C13B	116.9 (3)
C11A—C10A—H10A	118.4	O3B—C15B—H15D	109.5
C9A—C10A—H10A	118.4	O3B—C15B—H15E	109.5
C10A—C11A—C6A	116.9 (3)	H15D—C15B—H15E	109.5
C10A—C11A—C12A	121.1 (3)	O3B—C15B—H15F	109.5
C6A—C11A—C12A	121.8 (3)	H15D—C15B—H15F	109.5
N2A—C12A—C5A	121.7 (3)	H15E—C15B—H15F	109.5
N2A—C12A—C11A	117.7 (3)	C1A—N1A—C13A	117.4 (2)
C5A—C12A—C11A	120.5 (3)	C1A—N1A—Ru1	117.4 (2)
N2A—C13A—N1A	116.4 (2)	C13A—N1A—Ru1	125.10 (18)
N2A—C13A—C14A	123.4 (3)	C12A—N2A—C13A	118.3 (2)
N1A—C13A—C14A	120.2 (2)	C1B—N1B—C13B	118.4 (2)
C3A—C14A—C13A	120.0 (3)	C1B—N1B—Ru1	117.34 (18)
C3A—C14A—C4A	123.1 (3)	C13B—N1B—Ru1	123.91 (18)
C13A—C14A—C4A	116.8 (3)	C12B—N2B—C13B	119.0 (2)
O3A—C15A—H15A	109.5	C8A—O3A—C15A	117.3 (3)
O3A—C15A—H15B	109.5	C8B—O3B—C15B	118.1 (3)
H15A—C15A—H15B	109.5
N1A—C1A—C2A—C3A	−4.0 (5)	C9B—C10B—C11B—C12B	−176.9 (3)
C1A—C2A—C3A—C14A	2.9 (5)	C4B—C5B—C12B—N2B	2.3 (5)
C14A—C4A—C5A—C12A	1.9 (5)	C4B—C5B—C12B—C11B	−176.7 (3)
C11A—C6A—C7A—C8A	0.0 (6)	C6B—C11B—C12B—N2B	−179.8 (3)
C6A—C7A—C8A—O3A	178.2 (3)	C10B—C11B—C12B—N2B	−3.1 (4)
C6A—C7A—C8A—C9A	0.0 (6)	C6B—C11B—C12B—C5B	−0.8 (5)
O3A—C8A—C9A—C10A	−178.6 (3)	C10B—C11B—C12B—C5B	175.9 (3)
C7A—C8A—C9A—C10A	−0.5 (5)	C2B—C3B—C14B—C4B	−179.0 (3)
C8A—C9A—C10A—C11A	1.2 (6)	C2B—C3B—C14B—C13B	−0.1 (4)
C9A—C10A—C11A—C6A	−1.2 (5)	C5B—C4B—C14B—C3B	178.7 (3)
C9A—C10A—C11A—C12A	174.4 (3)	C5B—C4B—C14B—C13B	−0.3 (5)
C7A—C6A—C11A—C10A	0.6 (5)	N2B—C13B—C14B—C3B	−177.2 (3)
C7A—C6A—C11A—C12A	−175.0 (3)	N1B—C13B—C14B—C3B	2.6 (4)
C4A—C5A—C12A—N2A	−4.0 (5)	N2B—C13B—C14B—C4B	1.8 (4)
C4A—C5A—C12A—C11A	173.1 (3)	N1B—C13B—C14B—C4B	−178.4 (3)
C10A—C11A—C12A—N2A	22.8 (4)	C2A—C1A—N1A—C13A	−0.1 (4)
C6A—C11A—C12A—N2A	−161.9 (3)	C2A—C1A—N1A—Ru1	177.4 (2)
C10A—C11A—C12A—C5A	−154.4 (3)	N2A—C13A—N1A—C1A	−173.8 (2)
C6A—C11A—C12A—C5A	20.9 (4)	C14A—C13A—N1A—C1A	5.1 (4)
C2A—C3A—C14A—C13A	2.0 (4)	N2A—C13A—N1A—Ru1	8.8 (3)
C2A—C3A—C14A—C4A	179.5 (3)	C14A—C13A—N1A—Ru1	−172.28 (19)
N2A—C13A—C14A—C3A	172.7 (3)	C5A—C12A—N2A—C13A	1.4 (4)
N1A—C13A—C14A—C3A	−6.1 (4)	C11A—C12A—N2A—C13A	−175.7 (2)
N2A—C13A—C14A—C4A	−5.0 (4)	N1A—C13A—N2A—C12A	−178.1 (2)
N1A—C13A—C14A—C4A	176.2 (3)	C14A—C13A—N2A—C12A	3.1 (4)
C5A—C4A—C14A—C3A	−175.3 (3)	C2B—C1B—N1B—C13B	1.5 (4)
C5A—C4A—C14A—C13A	2.3 (5)	C2B—C1B—N1B—Ru1	−172.0 (2)
N1B—C1B—C2B—C3B	1.0 (5)	N2B—C13B—N1B—C1B	176.5 (2)
C1B—C2B—C3B—C14B	−1.6 (4)	C14B—C13B—N1B—C1B	−3.3 (4)
C14B—C4B—C5B—C12B	−1.6 (5)	N2B—C13B—N1B—Ru1	−10.4 (3)
C11B—C6B—C7B—C8B	0.5 (6)	C14B—C13B—N1B—Ru1	169.78 (19)
C6B—C7B—C8B—O3B	−177.5 (3)	C5B—C12B—N2B—C13B	−0.8 (4)
C6B—C7B—C8B—C9B	−0.4 (6)	C11B—C12B—N2B—C13B	178.3 (2)
O3B—C8B—C9B—C10B	176.9 (3)	N1B—C13B—N2B—C12B	178.9 (2)
C7B—C8B—C9B—C10B	0.1 (6)	C14B—C13B—N2B—C12B	−1.3 (4)
C8B—C9B—C10B—C11B	0.1 (6)	C7A—C8A—O3A—C15A	−173.9 (4)
C7B—C6B—C11B—C10B	−0.3 (5)	C9A—C8A—O3A—C15A	4.3 (5)
C7B—C6B—C11B—C12B	176.6 (3)	C9B—C8B—O3B—C15B	−6.4 (5)
C9B—C10B—C11B—C6B	0.0 (5)	C7B—C8B—O3B—C15B	170.5 (3)

cis-Dicarbonyldichloridobis[2-(2-methoxyphenyl)-1,8-naphthyridine-κN⁸]ruthenium(II) (Ru_B)

Crystal data

[RuCl2(C15H12N2O)2(CO)2]	F(000) = 2832
Mr = 700.54	Dx = 1.362 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.106 (3) Å	Cell parameters from 999 reflections
b = 12.1967 (16) Å	θ = 4.5–46.9°
c = 29.420 (4) Å	µ = 0.66 mm^−1
β = 94.918 (2)°	T = 296 K
V = 6830.5 (17) Å^3	Plate, yellow
Z = 8	0.27 × 0.26 × 0.05 mm

Data collection

Bruker SMART CCD area detector diffractometer	4821 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.047
phi and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2012)	h = −23→23
Tmin = 0.819, Tmax = 0.964	k = −15→15
26258 measured reflections	l = −36→36
6683 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0521P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.003
6683 reflections	Δρmax = 0.59 e Å^−3
391 parameters	Δρmin = −0.25 e Å^−3

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

17.6598 (0.0062) x + 4.4525 (0.0077) y - 5.5935 (0.0305) z = 6.8792 (0.0324)

* 0.0230 (0.0021) N1A * -0.0071 (0.0024) C1A * -0.0226 (0.0029) C2A * -0.0129 (0.0030) C3A * 0.0213 (0.0029) C14A * 0.0301 (0.0028) C4A * -0.0168 (0.0027) C5A * -0.0479 (0.0024) C12A * 0.0331 (0.0026) C13A

Rms deviation of fitted atoms = 0.0264

16.8111 (0.0161) x - 2.6580 (0.0200) y + 10.1581 (0.0481) z = 21.4846 (0.0347)

Angle to previous plane (with approximate esd) = 46.628 ( 0.084 )

* -0.0085 (0.0025) C11A * 0.0106 (0.0027) C6A * -0.0044 (0.0031) C7A * -0.0041 (0.0033) C8A * 0.0062 (0.0032) C9A * 0.0001 (0.0029) C10A

Rms deviation of fitted atoms = 0.0066

15.7087 (0.0111) x - 2.7250 (0.0130) y + 13.2720 (0.0204) z = 19.8080 (0.0133)

Angle to previous plane (with approximate esd) = 6.689 ( 0.180 )

* 0.0332 (0.0022) N1B * -0.0117 (0.0026) C1B * -0.0399 (0.0029) C2B * 0.0027 (0.0031) C3B * 0.0227 (0.0033) C14B * 0.0226 (0.0033) C4B * -0.0071 (0.0032) C5B * -0.0395 (0.0025) C12B * 0.0170 (0.0027) C13B

Rms deviation of fitted atoms = 0.0253

12.9586 (0.0229) x + 7.1267 (0.0168) y + 11.3506 (0.0425) z = 16.8405 (0.0261)

Angle to previous plane (with approximate esd) = 48.671 ( 0.109 )

* -0.0167 (0.0026) C11B * 0.0056 (0.0029) C6B * 0.0126 (0.0032) C7B * -0.0201 (0.0032) C8B * 0.0087 (0.0028) C9B * 0.0098 (0.0026) C10B

Rms deviation of fitted atoms = 0.0132

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

	x	y	z	Uiso*/Ueq
Ru1	0.58887 (2)	0.30746 (2)	0.88488 (2)	0.04548 (10)
C1	0.56541 (19)	0.3277 (3)	0.82276 (13)	0.0574 (9)
C2	0.67357 (18)	0.2447 (2)	0.87104 (10)	0.0475 (8)
C1A	0.60203 (18)	0.3902 (3)	0.98273 (12)	0.0595 (9)
H1A	0.5823	0.4505	0.9672	0.071*
C2A	0.6143 (2)	0.3975 (3)	1.02998 (12)	0.0670 (10)
H2A	0.6022	0.4607	1.0452	0.080*
C3A	0.6440 (2)	0.3115 (3)	1.05355 (12)	0.0640 (10)
H3A	0.6523	0.3148	1.0851	0.077*
C4A	0.69308 (18)	0.1225 (3)	1.05043 (12)	0.0602 (9)
H4A	0.7054	0.1214	1.0817	0.072*
C5A	0.70469 (18)	0.0335 (3)	1.02466 (12)	0.0593 (9)
H5A	0.7242	−0.0296	1.0382	0.071*
C6A	0.67341 (19)	−0.1639 (3)	0.95871 (14)	0.0630 (9)
C7A	0.6776 (2)	−0.2493 (3)	0.92799 (16)	0.0853 (13)
H7A	0.6616	−0.3187	0.9352	0.102*
C8A	0.7050 (3)	−0.2322 (4)	0.88716 (17)	0.0973 (15)
H8A	0.7076	−0.2903	0.8669	0.117*
C9A	0.7287 (3)	−0.1303 (3)	0.87556 (14)	0.0911 (14)
H9A	0.7478	−0.1194	0.8479	0.109*
C10A	0.7237 (2)	−0.0444 (3)	0.90576 (13)	0.0696 (10)
H10A	0.7394	0.0248	0.8981	0.083*
C11A	0.69602 (17)	−0.0591 (3)	0.94685 (12)	0.0529 (8)
C12A	0.68695 (17)	0.0370 (2)	0.97698 (11)	0.0481 (8)
C13A	0.64815 (16)	0.2151 (2)	0.98181 (10)	0.0434 (7)
C14A	0.66220 (17)	0.2167 (3)	1.02955 (11)	0.0507 (8)
C15A	0.6313 (3)	−0.2821 (3)	1.01492 (19)	0.1098 (17)
H15A	0.5923	−0.3119	0.9961	0.165*
H15B	0.6198	−0.2790	1.0460	0.165*
H15C	0.6718	−0.3281	1.0130	0.165*
C1B	0.50260 (16)	0.1337 (3)	0.92418 (11)	0.0532 (8)
H1B	0.4954	0.1919	0.9437	0.064*
C2B	0.47464 (19)	0.0325 (3)	0.93435 (13)	0.0659 (10)
H2B	0.4489	0.0240	0.9595	0.079*
C3B	0.4857 (2)	−0.0534 (3)	0.90678 (13)	0.0709 (11)
H3B	0.4690	−0.1226	0.9136	0.085*
C4B	0.5346 (2)	−0.1225 (3)	0.83629 (15)	0.0778 (11)
H4B	0.5195	−0.1937	0.8410	0.093*
C5B	0.5680 (2)	−0.0985 (3)	0.79948 (14)	0.0765 (11)
H5B	0.5761	−0.1533	0.7786	0.092*
C6B	0.6738 (2)	−0.0260 (4)	0.73118 (14)	0.0803 (12)
C7B	0.6971 (3)	0.0002 (5)	0.68881 (16)	0.0978 (16)
H7B	0.7323	−0.0414	0.6772	0.117*
C8B	0.6683 (3)	0.0867 (5)	0.66446 (15)	0.0948 (15)
H8B	0.6824	0.1012	0.6356	0.114*
C9B	0.6189 (2)	0.1530 (4)	0.68186 (14)	0.0834 (12)
H9B	0.6012	0.2137	0.6656	0.100*
C10B	0.59576 (19)	0.1281 (3)	0.72396 (13)	0.0671 (10)
H10B	0.5623	0.1728	0.7358	0.081*
C11B	0.62107 (19)	0.0389 (3)	0.74870 (12)	0.0636 (10)
C12B	0.59090 (18)	0.0096 (3)	0.79207 (12)	0.0569 (9)
C13B	0.54800 (16)	0.0672 (2)	0.85893 (10)	0.0466 (7)
C14B	0.52218 (18)	−0.0383 (3)	0.86826 (12)	0.0596 (9)
C15B	0.7537 (3)	−0.1769 (5)	0.7428 (2)	0.161 (3)
H15D	0.7384	−0.2082	0.7137	0.241*
H15E	0.7646	−0.2345	0.7645	0.241*
H15F	0.7948	−0.1330	0.7400	0.241*
Cl1	0.64502 (5)	0.48319 (7)	0.88440 (3)	0.0669 (3)
Cl2	0.47757 (5)	0.39313 (7)	0.89944 (3)	0.0690 (3)
N1A	0.61669 (14)	0.30300 (19)	0.95858 (9)	0.0482 (6)
N2A	0.66171 (13)	0.1268 (2)	0.95616 (8)	0.0461 (6)
N1B	0.53889 (12)	0.15319 (19)	0.88859 (8)	0.0454 (6)
N2B	0.58110 (13)	0.0906 (2)	0.82106 (8)	0.0487 (6)
O1	0.55373 (16)	0.3485 (2)	0.78538 (9)	0.0877 (9)
O2	0.72585 (13)	0.21316 (19)	0.86071 (8)	0.0642 (6)
O3A	0.64634 (15)	−0.1747 (2)	0.99962 (10)	0.0864 (9)
O3B	0.69909 (17)	−0.1099 (3)	0.75803 (10)	0.1120 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.05552 (18)	0.03555 (15)	0.04620 (17)	0.00224 (11)	0.00919 (12)	−0.00144 (11)
C1	0.061 (2)	0.050 (2)	0.061 (2)	−0.0001 (16)	0.0049 (18)	0.0035 (17)
C2	0.058 (2)	0.0405 (19)	0.0447 (19)	−0.0079 (16)	0.0083 (16)	0.0006 (14)
C1A	0.078 (2)	0.0421 (19)	0.059 (2)	0.0034 (17)	0.0140 (18)	−0.0096 (16)
C2A	0.089 (3)	0.053 (2)	0.061 (2)	0.003 (2)	0.014 (2)	−0.0231 (18)
C3A	0.080 (3)	0.066 (2)	0.047 (2)	0.002 (2)	0.0067 (18)	−0.0135 (18)
C4A	0.070 (2)	0.060 (2)	0.049 (2)	−0.0021 (18)	−0.0037 (17)	0.0020 (17)
C5A	0.065 (2)	0.054 (2)	0.058 (2)	0.0025 (17)	−0.0009 (17)	0.0083 (17)
C6A	0.064 (2)	0.041 (2)	0.084 (3)	0.0075 (16)	0.009 (2)	0.0012 (18)
C7A	0.103 (3)	0.043 (2)	0.111 (4)	0.005 (2)	0.016 (3)	−0.009 (2)
C8A	0.136 (4)	0.051 (3)	0.104 (4)	0.021 (3)	0.004 (3)	−0.024 (3)
C9A	0.136 (4)	0.070 (3)	0.070 (3)	0.027 (3)	0.025 (3)	−0.007 (2)
C10A	0.095 (3)	0.047 (2)	0.068 (2)	0.0121 (19)	0.014 (2)	0.0005 (18)
C11A	0.055 (2)	0.0396 (18)	0.064 (2)	0.0075 (15)	0.0041 (17)	0.0001 (16)
C12A	0.0515 (19)	0.0389 (17)	0.055 (2)	−0.0022 (14)	0.0077 (15)	−0.0006 (15)
C13A	0.0464 (18)	0.0370 (17)	0.0479 (18)	−0.0026 (13)	0.0091 (14)	−0.0034 (14)
C14A	0.054 (2)	0.052 (2)	0.0466 (18)	−0.0085 (16)	0.0069 (15)	−0.0055 (16)
C15A	0.107 (4)	0.061 (3)	0.170 (5)	0.006 (2)	0.062 (3)	0.029 (3)
C1B	0.052 (2)	0.056 (2)	0.053 (2)	0.0008 (16)	0.0112 (16)	−0.0034 (16)
C2B	0.064 (2)	0.069 (3)	0.068 (2)	−0.0077 (19)	0.0221 (19)	0.008 (2)
C3B	0.078 (3)	0.050 (2)	0.086 (3)	−0.0123 (19)	0.015 (2)	0.007 (2)
C4B	0.099 (3)	0.043 (2)	0.093 (3)	−0.008 (2)	0.016 (2)	−0.008 (2)
C5B	0.093 (3)	0.056 (2)	0.083 (3)	0.000 (2)	0.021 (2)	−0.023 (2)
C6B	0.076 (3)	0.108 (4)	0.058 (2)	0.013 (2)	0.010 (2)	−0.029 (2)
C7B	0.081 (3)	0.146 (5)	0.069 (3)	0.005 (3)	0.021 (3)	−0.039 (3)
C8B	0.085 (3)	0.141 (5)	0.060 (3)	−0.032 (3)	0.017 (2)	−0.018 (3)
C9B	0.075 (3)	0.104 (3)	0.071 (3)	−0.021 (3)	0.005 (2)	−0.007 (2)
C10B	0.059 (2)	0.078 (3)	0.067 (2)	−0.011 (2)	0.0132 (19)	−0.009 (2)
C11B	0.056 (2)	0.079 (3)	0.056 (2)	−0.0017 (19)	0.0069 (18)	−0.022 (2)
C12B	0.055 (2)	0.055 (2)	0.061 (2)	0.0035 (16)	0.0052 (17)	−0.0130 (17)
C13B	0.0459 (18)	0.0420 (18)	0.0525 (19)	−0.0008 (14)	0.0074 (15)	−0.0034 (15)
C14B	0.062 (2)	0.049 (2)	0.068 (2)	−0.0028 (17)	0.0120 (19)	−0.0022 (17)
C15B	0.151 (6)	0.196 (7)	0.139 (5)	0.103 (5)	0.034 (4)	−0.027 (4)
Cl1	0.0905 (7)	0.0397 (5)	0.0714 (6)	−0.0093 (4)	0.0113 (5)	−0.0003 (4)
Cl2	0.0699 (6)	0.0575 (6)	0.0818 (6)	0.0190 (4)	0.0184 (5)	0.0029 (5)
N1A	0.0611 (17)	0.0344 (14)	0.0503 (15)	0.0008 (12)	0.0115 (13)	−0.0060 (12)
N2A	0.0532 (16)	0.0385 (15)	0.0471 (15)	0.0017 (12)	0.0070 (12)	−0.0030 (12)
N1B	0.0452 (15)	0.0423 (14)	0.0493 (15)	0.0020 (12)	0.0080 (12)	−0.0023 (12)
N2B	0.0486 (15)	0.0469 (16)	0.0509 (16)	−0.0011 (12)	0.0060 (12)	−0.0046 (12)
O1	0.118 (2)	0.083 (2)	0.0593 (17)	0.0010 (17)	−0.0108 (16)	0.0090 (15)
O2	0.0567 (15)	0.0662 (16)	0.0715 (17)	0.0041 (12)	0.0160 (13)	0.0074 (12)
O3A	0.107 (2)	0.0470 (16)	0.112 (2)	0.0017 (14)	0.0458 (19)	0.0099 (14)
O3B	0.118 (3)	0.141 (3)	0.079 (2)	0.068 (2)	0.0205 (18)	−0.022 (2)

Geometric parameters (Å, º)

Ru1—C1	1.861 (4)	C15A—O3A	1.423 (4)
Ru1—C2	1.867 (4)	C15A—H15A	0.9600
Ru1—N1B	2.117 (2)	C15A—H15B	0.9600
Ru1—N1A	2.188 (3)	C15A—H15C	0.9600
Ru1—Cl1	2.3974 (9)	C1B—N1B	1.326 (4)
Ru1—Cl2	2.4400 (9)	C1B—C2B	1.388 (5)
C1—O1	1.132 (4)	C1B—H1B	0.9300
C2—O2	1.136 (3)	C2B—C3B	1.353 (5)
C1A—N1A	1.322 (4)	C2B—H2B	0.9300
C1A—C2A	1.393 (5)	C3B—C14B	1.392 (5)
C1A—H1A	0.9300	C3B—H3B	0.9300
C2A—C3A	1.355 (5)	C4B—C5B	1.336 (5)
C2A—H2A	0.9300	C4B—C14B	1.426 (5)
C3A—C14A	1.414 (4)	C4B—H4B	0.9300
C3A—H3A	0.9300	C5B—C12B	1.412 (5)
C4A—C5A	1.353 (4)	C5B—H5B	0.9300
C4A—C14A	1.409 (5)	C6B—O3B	1.357 (5)
C4A—H4A	0.9300	C6B—C7B	1.396 (6)
C5A—C12A	1.415 (4)	C6B—C11B	1.414 (5)
C5A—H5A	0.9300	C7B—C8B	1.365 (6)
C6A—O3A	1.356 (4)	C7B—H7B	0.9300
C6A—C7A	1.385 (5)	C8B—C9B	1.375 (6)
C6A—C11A	1.403 (5)	C8B—H8B	0.9300
C7A—C8A	1.367 (6)	C9B—C10B	1.384 (5)
C7A—H7A	0.9300	C9B—H9B	0.9300
C8A—C9A	1.376 (6)	C10B—C11B	1.373 (5)
C8A—H8A	0.9300	C10B—H10B	0.9300
C9A—C10A	1.382 (5)	C11B—C12B	1.488 (5)
C9A—H9A	0.9300	C12B—N2B	1.329 (4)
C10A—C11A	1.372 (5)	C13B—N2B	1.358 (4)
C10A—H10A	0.9300	C13B—N1B	1.385 (4)
C11A—C12A	1.489 (4)	C13B—C14B	1.413 (4)
C12A—N2A	1.326 (4)	C15B—O3B	1.426 (5)
C13A—N2A	1.353 (4)	C15B—H15D	0.9600
C13A—N1A	1.381 (4)	C15B—H15E	0.9600
C13A—C14A	1.407 (4)	C15B—H15F	0.9600
C1—Ru1—C2	88.89 (14)	O3A—C15A—H15C	109.5
C1—Ru1—N1B	95.56 (12)	H15A—C15A—H15C	109.5
C2—Ru1—N1B	92.86 (11)	H15B—C15A—H15C	109.5
C1—Ru1—N1A	173.79 (12)	N1B—C1B—C2B	124.5 (3)
C2—Ru1—N1A	93.70 (11)	N1B—C1B—H1B	117.7
N1B—Ru1—N1A	89.95 (9)	C2B—C1B—H1B	117.7
C1—Ru1—Cl1	86.89 (11)	C3B—C2B—C1B	118.5 (3)
C2—Ru1—Cl1	88.22 (9)	C3B—C2B—H2B	120.8
N1B—Ru1—Cl1	177.34 (7)	C1B—C2B—H2B	120.8
N1A—Ru1—Cl1	87.55 (7)	C2B—C3B—C14B	120.0 (3)
C1—Ru1—Cl2	88.59 (11)	C2B—C3B—H3B	120.0
C2—Ru1—Cl2	177.36 (9)	C14B—C3B—H3B	120.0
N1B—Ru1—Cl2	88.16 (7)	C5B—C4B—C14B	119.7 (4)
N1A—Ru1—Cl2	88.74 (7)	C5B—C4B—H4B	120.2
Cl1—Ru1—Cl2	90.88 (3)	C14B—C4B—H4B	120.2
O1—C1—Ru1	174.2 (3)	C4B—C5B—C12B	120.4 (3)
O2—C2—Ru1	174.9 (3)	C4B—C5B—H5B	119.8
N1A—C1A—C2A	124.3 (3)	C12B—C5B—H5B	119.8
N1A—C1A—H1A	117.9	O3B—C6B—C7B	124.6 (4)
C2A—C1A—H1A	117.9	O3B—C6B—C11B	116.1 (4)
C3A—C2A—C1A	119.2 (3)	C7B—C6B—C11B	119.3 (5)
C3A—C2A—H2A	120.4	C8B—C7B—C6B	120.0 (4)
C1A—C2A—H2A	120.4	C8B—C7B—H7B	120.0
C2A—C3A—C14A	119.2 (3)	C6B—C7B—H7B	120.0
C2A—C3A—H3A	120.4	C7B—C8B—C9B	121.2 (4)
C14A—C3A—H3A	120.4	C7B—C8B—H8B	119.4
C5A—C4A—C14A	119.5 (3)	C9B—C8B—H8B	119.4
C5A—C4A—H4A	120.2	C8B—C9B—C10B	119.1 (5)
C14A—C4A—H4A	120.2	C8B—C9B—H9B	120.5
C4A—C5A—C12A	119.6 (3)	C10B—C9B—H9B	120.5
C4A—C5A—H5A	120.2	C11B—C10B—C9B	121.6 (4)
C12A—C5A—H5A	120.2	C11B—C10B—H10B	119.2
O3A—C6A—C7A	123.6 (4)	C9B—C10B—H10B	119.2
O3A—C6A—C11A	117.2 (3)	C10B—C11B—C6B	118.7 (4)
C7A—C6A—C11A	119.1 (4)	C10B—C11B—C12B	120.0 (3)
C8A—C7A—C6A	120.4 (4)	C6B—C11B—C12B	121.3 (4)
C8A—C7A—H7A	119.8	N2B—C12B—C5B	122.2 (3)
C6A—C7A—H7A	119.8	N2B—C12B—C11B	117.3 (3)
C7A—C8A—C9A	121.0 (4)	C5B—C12B—C11B	120.3 (3)
C7A—C8A—H8A	119.5	N2B—C13B—N1B	116.7 (3)
C9A—C8A—H8A	119.5	N2B—C13B—C14B	123.1 (3)
C8A—C9A—C10A	118.9 (4)	N1B—C13B—C14B	120.2 (3)
C8A—C9A—H9A	120.6	C3B—C14B—C13B	119.1 (3)
C10A—C9A—H9A	120.6	C3B—C14B—C4B	124.4 (3)
C11A—C10A—C9A	121.4 (4)	C13B—C14B—C4B	116.5 (3)
C11A—C10A—H10A	119.3	O3B—C15B—H15D	109.5
C9A—C10A—H10A	119.3	O3B—C15B—H15E	109.5
C10A—C11A—C6A	119.2 (3)	H15D—C15B—H15E	109.5
C10A—C11A—C12A	119.7 (3)	O3B—C15B—H15F	109.5
C6A—C11A—C12A	121.0 (3)	H15D—C15B—H15F	109.5
N2A—C12A—C5A	122.0 (3)	H15E—C15B—H15F	109.5
N2A—C12A—C11A	115.6 (3)	C1A—N1A—C13A	117.5 (3)
C5A—C12A—C11A	122.4 (3)	C1A—N1A—Ru1	117.9 (2)
N2A—C13A—N1A	116.0 (3)	C13A—N1A—Ru1	124.62 (19)
N2A—C13A—C14A	122.6 (3)	C12A—N2A—C13A	118.7 (3)
N1A—C13A—C14A	121.4 (3)	C1B—N1B—C13B	117.7 (3)
C13A—C14A—C4A	117.4 (3)	C1B—N1B—Ru1	117.9 (2)
C13A—C14A—C3A	118.4 (3)	C13B—N1B—Ru1	124.0 (2)
C4A—C14A—C3A	124.1 (3)	C12B—N2B—C13B	118.1 (3)
O3A—C15A—H15A	109.5	C6A—O3A—C15A	118.2 (3)
O3A—C15A—H15B	109.5	C6B—O3B—C15B	118.8 (4)
H15A—C15A—H15B	109.5
N1A—C1A—C2A—C3A	1.0 (6)	O3B—C6B—C11B—C12B	−5.4 (6)
C1A—C2A—C3A—C14A	0.4 (6)	C7B—C6B—C11B—C12B	175.5 (4)
C14A—C4A—C5A—C12A	1.2 (5)	C4B—C5B—C12B—N2B	0.6 (6)
O3A—C6A—C7A—C8A	179.4 (4)	C4B—C5B—C12B—C11B	−173.4 (4)
C11A—C6A—C7A—C8A	1.6 (6)	C10B—C11B—C12B—N2B	−45.4 (5)
C6A—C7A—C8A—C9A	−0.2 (7)	C6B—C11B—C12B—N2B	137.1 (4)
C7A—C8A—C9A—C10A	−0.8 (7)	C10B—C11B—C12B—C5B	128.8 (4)
C8A—C9A—C10A—C11A	0.4 (7)	C6B—C11B—C12B—C5B	−48.6 (5)
C9A—C10A—C11A—C6A	1.0 (6)	C2B—C3B—C14B—C13B	0.9 (6)
C9A—C10A—C11A—C12A	−175.8 (4)	C2B—C3B—C14B—C4B	−177.8 (4)
O3A—C6A—C11A—C10A	−179.9 (3)	N2B—C13B—C14B—C3B	−176.7 (3)
C7A—C6A—C11A—C10A	−2.0 (5)	N1B—C13B—C14B—C3B	2.0 (5)
O3A—C6A—C11A—C12A	−3.2 (5)	N2B—C13B—C14B—C4B	2.1 (5)
C7A—C6A—C11A—C12A	174.7 (3)	N1B—C13B—C14B—C4B	−179.2 (3)
C4A—C5A—C12A—N2A	2.8 (5)	C5B—C4B—C14B—C3B	177.5 (4)
C4A—C5A—C12A—C11A	−177.9 (3)	C5B—C4B—C14B—C13B	−1.2 (6)
C10A—C11A—C12A—N2A	42.6 (4)	C2A—C1A—N1A—C13A	−2.1 (5)
C6A—C11A—C12A—N2A	−134.1 (3)	C2A—C1A—N1A—Ru1	177.5 (3)
C10A—C11A—C12A—C5A	−136.7 (4)	N2A—C13A—N1A—C1A	179.3 (3)
C6A—C11A—C12A—C5A	46.5 (5)	C14A—C13A—N1A—C1A	1.9 (4)
N2A—C13A—C14A—C4A	1.5 (5)	N2A—C13A—N1A—Ru1	−0.3 (4)
N1A—C13A—C14A—C4A	178.7 (3)	C14A—C13A—N1A—Ru1	−177.7 (2)
N2A—C13A—C14A—C3A	−177.9 (3)	C5A—C12A—N2A—C13A	−4.6 (4)
N1A—C13A—C14A—C3A	−0.6 (5)	C11A—C12A—N2A—C13A	176.0 (3)
C5A—C4A—C14A—C13A	−3.2 (5)	N1A—C13A—N2A—C12A	−174.9 (3)
C5A—C4A—C14A—C3A	176.1 (3)	C14A—C13A—N2A—C12A	2.4 (4)
C2A—C3A—C14A—C13A	−0.5 (5)	C2B—C1B—N1B—C13B	1.7 (5)
C2A—C3A—C14A—C4A	−179.8 (3)	C2B—C1B—N1B—Ru1	−171.4 (3)
N1B—C1B—C2B—C3B	1.1 (5)	N2B—C13B—N1B—C1B	175.6 (3)
C1B—C2B—C3B—C14B	−2.4 (6)	C14B—C13B—N1B—C1B	−3.2 (4)
C14B—C4B—C5B—C12B	−0.1 (6)	N2B—C13B—N1B—Ru1	−11.8 (4)
O3B—C6B—C7B—C8B	−179.8 (4)	C14B—C13B—N1B—Ru1	169.4 (2)
C11B—C6B—C7B—C8B	−0.9 (7)	C5B—C12B—N2B—C13B	0.2 (5)
C6B—C7B—C8B—C9B	3.4 (7)	C11B—C12B—N2B—C13B	174.3 (3)
C7B—C8B—C9B—C10B	−3.0 (7)	N1B—C13B—N2B—C12B	179.7 (3)
C8B—C9B—C10B—C11B	0.0 (6)	C14B—C13B—N2B—C12B	−1.6 (5)
C9B—C10B—C11B—C6B	2.4 (6)	C7A—C6A—O3A—C15A	10.0 (6)
C9B—C10B—C11B—C12B	−175.1 (3)	C11A—C6A—O3A—C15A	−172.2 (4)
O3B—C6B—C11B—C10B	177.1 (4)	C7B—C6B—O3B—C15B	0.5 (7)
C7B—C6B—C11B—C10B	−1.9 (6)	C11B—C6B—O3B—C15B	−178.5 (5)