cis-Bis(2,2'-bipyridine-κ(2)N,N')bis-(pyridin-4-amine-κN(1))ruthenium(II) bis-(hexa-fluoridophosphate) acetonitrile monosolvate.

In the title complex, [Ru(C(10)H(8)N(2))(2)(C(5)H(6)N(2))(2)](PF(6))(2)·CH(3)CN, the Ru(II) atom is bonded to two α-diimine ligands, viz. 2,2'-bipyridine, in a cis configuration and to two 4-amino-pyridine (4Apy) ligands in the expected distorted octa-hedral configuration. The compound is isostructural with [Ru(C(10)H(8)N(2))(2)(C(5)H(6)N(2))(2)](ClO(4))(2)·CH(3)CN [Duan et al. (1999 ▶). J. Coord. Chem.46, 301-312] and both structures are stabilized by classical hydrogen bonds between 4Apy ligands as donors and counter-ions and acetonitrile solvent mol-ecules as acceptors. Indeed, N-H⋯F inter-actions give rise to an inter-molecularly locked assembly of two centrosymmetric complex mol-ecules and two PF(6) (-) counter-ions, which can be considered as the building units of both crystal architectures. The building blocks are connected to one another through hydrogen bonds between 4Apy and the connecting pieces made up of two centrosymmetric motifs with PF(6) (-) ions and acetonitrile mol-ecules, giving rise to ribbons running parallel to [011]. 2(1)-Screw-axis-related complex mol-ecules and PF(6) (-) counter-ions alternate in helical chains formed along the a axis by means of these contacts.

Related literature

For compounds with similar properties, see: Stoyanov et al. (2002 ▶); Duan et al. (1999 ▶); Salassa et al. (2009 ▶). For use of 4Apy, see: Sinha & Shrivastava (2012 ▶). For the synthesis of the starting materials, see: Bonneson et al. (1983 ▶).

Experimental

Crystal data

[Ru(C10H8N2)2(C5H6N2)2](PF6)2·C2H3N

M = 932.67

Triclinic,

a = 10.8290 (3) Å

b = 11.8890 (3) Å

c = 16.1020 (4) Å

α = 104.073 (1)°

β = 99.114 (2)°

γ = 107.761 (2)°

V = 1853.32 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.61 mm−1

T = 298 K

0.21 × 0.11 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.935, T max = 0.950

14506 measured reflections

7906 independent reflections

6142 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.148

S = 1.06

7906 reflections

506 parameters

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −0.58 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812052002/bg2496sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812052002/bg2496Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ru(C10H8N2)2(C5H6N2)2](PF6)2·C2H3N	Z = 2
Mr = 932.67	F(000) = 936
Triclinic, P1	Dx = 1.671 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.8290 (3) Å	Cell parameters from 14506 reflections
b = 11.8890 (3) Å	θ = 2.9–27.2°
c = 16.1020 (4) Å	µ = 0.61 mm−1
α = 104.073 (1)°	T = 298 K
β = 99.114 (2)°	Prism, red
γ = 107.761 (2)°	0.21 × 0.11 × 0.09 mm
V = 1853.32 (8) Å3

Nonius KappaCCD diffractometer	6142 reflections with I > 2σ(I)
CCD scans	Rint = 0.033
Absorption correction: multi-scan (Blessing, 1995)	θmax = 27.2°, θmin = 2.9°
Tmin = 0.935, Tmax = 0.950	h = −13→12
14506 measured reflections	k = −14→14
7906 independent reflections	l = −20→20

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053	w = 1/[σ2(Fo2) + (0.081P)2 + 1.5061P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.148	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.90 e Å−3
7906 reflections	Δρmin = −0.58 e Å−3
506 parameters

	x	y	z	Uiso*/Ueq
Ru	0.31099 (3)	0.67417 (3)	0.268302 (19)	0.03972 (12)
N1	0.3873 (3)	0.8658 (3)	0.3076 (2)	0.0457 (7)
N2	0.4801 (3)	0.7109 (3)	0.3647 (2)	0.0473 (7)
N2A	0.4008 (3)	0.6761 (3)	0.1657 (2)	0.0444 (7)
N1A	0.1542 (3)	0.6540 (3)	0.1681 (2)	0.0428 (7)
N3	0.2084 (3)	0.6776 (3)	0.3689 (2)	0.0427 (7)
N4	0.0286 (5)	0.6996 (5)	0.5798 (3)	0.0827 (13)
H4A	−0.0134	0.7501	0.5909	0.099*
H4B	0.0333	0.6524	0.6122	0.099*
N3A	0.2449 (3)	0.4776 (3)	0.2282 (2)	0.0420 (7)
N4A	0.0979 (5)	0.0921 (4)	0.1192 (3)	0.0834 (14)
H4A1	0.017	0.049	0.1171	0.1*
H4A2	0.1488	0.0558	0.098	0.1*
C1	0.3343 (5)	0.9383 (4)	0.2738 (3)	0.0588 (11)
H1	0.2531	0.9009	0.2312	0.071*
C2	0.3946 (6)	1.0650 (4)	0.2994 (4)	0.0705 (13)
H2	0.3546	1.1124	0.2748	0.085*
C3	0.5142 (6)	1.1206 (5)	0.3616 (4)	0.0785 (15)
H3	0.558	1.2063	0.3791	0.094*
C4	0.5690 (5)	1.0480 (5)	0.3980 (4)	0.0727 (14)
H4	0.6494	1.0846	0.4415	0.087*
C5	0.5051 (4)	0.9214 (4)	0.3701 (3)	0.0510 (10)
C6	0.5564 (4)	0.8353 (4)	0.4037 (3)	0.0526 (10)
C7	0.6732 (5)	0.8742 (5)	0.4703 (3)	0.0750 (14)
H7	0.7231	0.9584	0.4966	0.09*
C8	0.7141 (5)	0.7874 (6)	0.4966 (4)	0.0846 (17)
H8	0.7926	0.8119	0.5404	0.102*
C9	0.6390 (6)	0.6658 (6)	0.4582 (4)	0.0856 (18)
H9	0.6647	0.6058	0.476	0.103*
C10	0.5253 (5)	0.6317 (5)	0.3930 (3)	0.0693 (13)
H10	0.4763	0.5473	0.3668	0.083*
C10A	0.5286 (4)	0.6843 (4)	0.1691 (3)	0.0577 (11)
H10A	0.5829	0.6892	0.2217	0.069*
C9A	0.5807 (5)	0.6855 (5)	0.0966 (4)	0.0733 (14)
H9A	0.6694	0.6921	0.1008	0.088*
C8A	0.5032 (6)	0.6772 (6)	0.0192 (4)	0.0804 (15)
H8A	0.537	0.6753	−0.0305	0.097*
C7A	0.3718 (5)	0.6716 (5)	0.0148 (3)	0.0713 (14)
H7A	0.3175	0.6678	−0.0374	0.086*
C6A	0.3240 (4)	0.6716 (4)	0.0888 (3)	0.0497 (9)
C5A	0.1874 (4)	0.6646 (4)	0.0911 (3)	0.0475 (9)
C4A	0.0962 (5)	0.6651 (5)	0.0210 (3)	0.0609 (11)
H4A3	0.1212	0.6742	−0.0303	0.073*
C3A	−0.0327 (5)	0.6521 (5)	0.0278 (3)	0.0712 (14)
H3A	−0.0948	0.6544	−0.0182	0.085*
C2A	−0.0675 (4)	0.6356 (5)	0.1033 (3)	0.0635 (12)
H2A	−0.1548	0.6228	0.1082	0.076*
C1A	0.0277 (4)	0.6383 (4)	0.1717 (3)	0.0506 (9)
H1A	0.0031	0.6288	0.223	0.061*
C11	0.2122 (5)	0.6049 (4)	0.4215 (3)	0.0607 (11)
H11	0.2557	0.5487	0.4094	0.073*
C12	0.1551 (5)	0.6104 (5)	0.4914 (3)	0.0642 (12)
H12	0.1604	0.559	0.5261	0.077*
C13	0.0881 (4)	0.6942 (4)	0.5106 (3)	0.0564 (10)
C14	0.0837 (4)	0.7662 (4)	0.4576 (3)	0.0595 (11)
H14	0.04	0.8226	0.4677	0.071*
C15	0.1447 (4)	0.7554 (4)	0.3884 (3)	0.0558 (10)
H15	0.1406	0.8063	0.3532	0.067*
C11A	0.3199 (4)	0.4140 (4)	0.1952 (3)	0.0501 (9)
H11A	0.4075	0.4593	0.1968	0.06*
C12A	0.2760 (4)	0.2877 (4)	0.1598 (3)	0.0533 (10)
H12A	0.3332	0.2497	0.1387	0.064*
C13A	0.1447 (4)	0.2160 (4)	0.1555 (3)	0.0544 (10)
C14A	0.0678 (4)	0.2799 (4)	0.1908 (3)	0.0558 (10)
H14A	−0.0194	0.2362	0.1912	0.067*
C15A	0.1186 (4)	0.4061 (4)	0.2248 (3)	0.0485 (9)
H15A	0.0634	0.4457	0.247	0.058*
P1	0.07844 (14)	0.04876 (12)	0.70888 (9)	0.0660 (3)
P1A	0.71818 (12)	0.40171 (12)	0.25261 (9)	0.0604 (3)
F1	−0.0516 (5)	0.0689 (5)	0.7229 (5)	0.158 (2)
F2	0.1439 (5)	0.1892 (3)	0.7154 (3)	0.1230 (15)
F3	0.2117 (6)	0.0324 (7)	0.6988 (4)	0.172 (3)
F4	0.0089 (7)	−0.0907 (4)	0.7029 (3)	0.160 (2)
F5	0.1258 (5)	0.0774 (5)	0.8116 (3)	0.1387 (18)
F6	0.0318 (6)	0.0146 (5)	0.6062 (3)	0.148 (2)
F6A	0.7482 (4)	0.2948 (4)	0.2846 (3)	0.1114 (12)
F4A	0.6327 (5)	0.4106 (5)	0.3225 (3)	0.1294 (15)
F1A	0.6852 (5)	0.5050 (4)	0.2214 (4)	0.1450 (19)
F2A	0.8037 (3)	0.3839 (5)	0.1829 (2)	0.1177 (15)
F5A	0.5890 (3)	0.3042 (4)	0.1804 (2)	0.1011 (11)
F3A	0.8512 (4)	0.4961 (4)	0.3229 (3)	0.1229 (15)
C2S	0.6126 (9)	0.0190 (7)	0.1288 (5)	0.112 (2)
H3S	0.5892	−0.0603	0.1389	0.168*
H2S	0.5333	0.0381	0.1152	0.168*
H1S	0.6742	0.0818	0.181	0.168*
C1S	0.6767 (9)	0.0151 (7)	0.0534 (8)	0.124 (3)
N1S	0.7190 (10)	0.0059 (9)	−0.0082 (8)	0.189 (5)

	U11	U22	U33	U12	U13	U23
Ru	0.03023 (16)	0.03983 (18)	0.04288 (19)	0.01056 (12)	0.00455 (11)	0.00750 (12)
N1	0.0382 (16)	0.0436 (17)	0.0499 (18)	0.0110 (14)	0.0133 (14)	0.0083 (14)
N2	0.0422 (17)	0.0511 (19)	0.0462 (18)	0.0193 (15)	0.0089 (14)	0.0085 (15)
N2A	0.0359 (16)	0.0404 (16)	0.0518 (18)	0.0096 (13)	0.0121 (14)	0.0099 (14)
N1A	0.0353 (15)	0.0386 (16)	0.0456 (17)	0.0104 (13)	0.0058 (13)	0.0038 (13)
N3	0.0407 (16)	0.0438 (17)	0.0430 (17)	0.0165 (14)	0.0083 (13)	0.0117 (13)
N4	0.097 (3)	0.095 (3)	0.070 (3)	0.043 (3)	0.039 (3)	0.029 (2)
N3A	0.0344 (15)	0.0393 (16)	0.0504 (18)	0.0122 (13)	0.0104 (13)	0.0118 (13)
N4A	0.080 (3)	0.043 (2)	0.116 (4)	0.010 (2)	0.043 (3)	0.010 (2)
C1	0.057 (3)	0.052 (2)	0.066 (3)	0.017 (2)	0.014 (2)	0.019 (2)
C2	0.088 (4)	0.047 (3)	0.079 (3)	0.021 (2)	0.028 (3)	0.023 (2)
C3	0.080 (4)	0.045 (3)	0.093 (4)	0.001 (2)	0.025 (3)	0.014 (3)
C4	0.051 (3)	0.060 (3)	0.078 (3)	−0.002 (2)	0.009 (2)	0.003 (2)
C5	0.0359 (19)	0.054 (2)	0.050 (2)	0.0053 (17)	0.0118 (16)	0.0071 (18)
C6	0.0354 (19)	0.062 (3)	0.046 (2)	0.0087 (18)	0.0082 (16)	0.0034 (19)
C7	0.044 (2)	0.085 (4)	0.066 (3)	0.009 (2)	−0.004 (2)	0.001 (3)
C8	0.057 (3)	0.105 (5)	0.069 (3)	0.035 (3)	−0.016 (2)	0.000 (3)
C9	0.079 (4)	0.105 (5)	0.075 (3)	0.059 (4)	−0.006 (3)	0.014 (3)
C10	0.064 (3)	0.073 (3)	0.065 (3)	0.036 (3)	−0.004 (2)	0.010 (2)
C10A	0.039 (2)	0.062 (3)	0.067 (3)	0.0166 (19)	0.0152 (19)	0.012 (2)
C9A	0.050 (3)	0.085 (4)	0.092 (4)	0.027 (2)	0.033 (3)	0.024 (3)
C8A	0.072 (3)	0.104 (4)	0.070 (3)	0.032 (3)	0.035 (3)	0.024 (3)
C7A	0.060 (3)	0.092 (4)	0.054 (3)	0.017 (3)	0.020 (2)	0.018 (2)
C6A	0.041 (2)	0.051 (2)	0.048 (2)	0.0099 (17)	0.0080 (17)	0.0097 (18)
C5A	0.042 (2)	0.048 (2)	0.045 (2)	0.0130 (17)	0.0066 (16)	0.0086 (17)
C4A	0.055 (3)	0.072 (3)	0.050 (2)	0.019 (2)	0.0047 (19)	0.020 (2)
C3A	0.059 (3)	0.090 (4)	0.060 (3)	0.034 (3)	−0.007 (2)	0.018 (3)
C2A	0.041 (2)	0.075 (3)	0.066 (3)	0.027 (2)	0.001 (2)	0.008 (2)
C1A	0.037 (2)	0.055 (2)	0.055 (2)	0.0171 (17)	0.0059 (17)	0.0096 (19)
C11	0.069 (3)	0.064 (3)	0.050 (2)	0.028 (2)	0.012 (2)	0.015 (2)
C12	0.074 (3)	0.065 (3)	0.052 (3)	0.024 (2)	0.012 (2)	0.020 (2)
C13	0.055 (2)	0.056 (2)	0.048 (2)	0.015 (2)	0.0139 (19)	0.0045 (19)
C14	0.055 (3)	0.055 (3)	0.061 (3)	0.022 (2)	0.007 (2)	0.006 (2)
C15	0.052 (2)	0.055 (2)	0.055 (2)	0.019 (2)	0.0071 (19)	0.0100 (19)
C11A	0.0355 (19)	0.052 (2)	0.062 (2)	0.0144 (17)	0.0129 (17)	0.0172 (19)
C12A	0.049 (2)	0.048 (2)	0.065 (3)	0.0211 (19)	0.020 (2)	0.0151 (19)
C13A	0.055 (2)	0.047 (2)	0.058 (2)	0.0147 (19)	0.0173 (19)	0.0139 (19)
C14A	0.042 (2)	0.053 (2)	0.064 (3)	0.0072 (18)	0.0164 (19)	0.013 (2)
C15A	0.039 (2)	0.051 (2)	0.056 (2)	0.0157 (17)	0.0149 (17)	0.0159 (18)
P1	0.0642 (8)	0.0582 (7)	0.0740 (8)	0.0224 (6)	0.0170 (6)	0.0175 (6)
P1A	0.0514 (6)	0.0643 (7)	0.0654 (7)	0.0217 (6)	0.0145 (5)	0.0186 (6)
F1	0.099 (3)	0.173 (5)	0.260 (7)	0.081 (3)	0.076 (4)	0.105 (5)
F2	0.141 (4)	0.070 (2)	0.132 (3)	0.005 (2)	0.034 (3)	0.027 (2)
F3	0.157 (4)	0.269 (7)	0.213 (6)	0.147 (5)	0.121 (4)	0.149 (5)
F4	0.271 (7)	0.063 (2)	0.164 (4)	0.047 (3)	0.119 (5)	0.042 (2)
F5	0.119 (3)	0.183 (5)	0.088 (3)	0.015 (3)	0.015 (2)	0.054 (3)
F6	0.181 (5)	0.123 (4)	0.082 (3)	−0.003 (3)	0.002 (3)	0.021 (2)
F6A	0.124 (3)	0.105 (3)	0.116 (3)	0.056 (2)	0.015 (2)	0.044 (2)
F4A	0.151 (4)	0.158 (4)	0.112 (3)	0.080 (3)	0.075 (3)	0.042 (3)
F1A	0.171 (5)	0.104 (3)	0.177 (5)	0.064 (3)	0.015 (4)	0.074 (3)
F2A	0.0598 (19)	0.208 (5)	0.081 (2)	0.044 (2)	0.0248 (17)	0.038 (3)
F5A	0.0564 (18)	0.117 (3)	0.102 (3)	0.0137 (18)	0.0072 (17)	0.016 (2)
F3A	0.107 (3)	0.113 (3)	0.086 (2)	−0.016 (2)	−0.014 (2)	0.017 (2)
C2S	0.136 (7)	0.096 (5)	0.105 (5)	0.060 (5)	0.026 (5)	0.012 (4)
C1S	0.100 (6)	0.089 (5)	0.161 (9)	0.049 (5)	−0.011 (5)	0.007 (5)
N1S	0.179 (9)	0.139 (7)	0.257 (12)	0.057 (6)	0.133 (9)	0.027 (7)

Ru—N2A	2.047 (3)	C8A—H8A	0.93
Ru—N2	2.059 (3)	C7A—C6A	1.372 (6)
Ru—N1A	2.058 (3)	C7A—H7A	0.93
Ru—N1	2.063 (3)	C6A—C5A	1.463 (5)
Ru—N3	2.104 (3)	C5A—C4A	1.380 (6)
Ru—N3A	2.119 (3)	C4A—C3A	1.381 (7)
N1—C1	1.341 (5)	C4A—H4A3	0.93
N1—C5	1.354 (5)	C3A—C2A	1.370 (7)
N2—C10	1.324 (6)	C3A—H3A	0.93
N2—C6	1.379 (5)	C2A—C1A	1.371 (6)
N2A—C10A	1.349 (5)	C2A—H2A	0.93
N2A—C6A	1.358 (5)	C1A—H1A	0.93
N1A—C1A	1.338 (5)	C11—C12	1.365 (7)
N1A—C5A	1.369 (5)	C11—H11	0.93
N3—C15	1.321 (5)	C12—C13	1.406 (7)
N3—C11	1.353 (6)	C12—H12	0.93
N4—C13	1.372 (6)	C13—C14	1.353 (7)
N4—H4A	0.86	C14—C15	1.382 (6)
N4—H4B	0.86	C14—H14	0.93
N3A—C11A	1.352 (5)	C15—H15	0.93
N3A—C15A	1.357 (5)	C11A—C12A	1.367 (6)
N4A—C13A	1.342 (6)	C11A—H11A	0.93
N4A—H4A1	0.86	C12A—C13A	1.398 (6)
N4A—H4A2	0.86	C12A—H12A	0.93
C1—C2	1.371 (6)	C13A—C14A	1.386 (6)
C1—H1	0.93	C14A—C15A	1.362 (6)
C2—C3	1.365 (8)	C14A—H14A	0.93
C2—H2	0.93	C15A—H15A	0.93
C3—C4	1.374 (8)	P1—F1	1.540 (4)
C3—H3	0.93	P1—F3	1.542 (5)
C4—C5	1.372 (6)	P1—F6	1.561 (4)
C4—H4	0.93	P1—F5	1.570 (4)
C5—C6	1.474 (6)	P1—F4	1.570 (4)
C6—C7	1.391 (6)	P1—F2	1.572 (4)
C7—C8	1.369 (8)	P1A—F1A	1.548 (4)
C7—H7	0.93	P1A—F4A	1.570 (4)
C8—C9	1.349 (9)	P1A—F5A	1.579 (3)
C8—H8	0.93	P1A—F3A	1.580 (4)
C9—C10	1.364 (7)	P1A—F2A	1.581 (4)
C9—H9	0.93	P1A—F6A	1.582 (4)
C10—H10	0.93	C2S—C1S	1.489 (13)
C10A—C9A	1.376 (7)	C2S—H3S	0.96
C10A—H10A	0.93	C2S—H2S	0.96
C9A—C8A	1.350 (8)	C2S—H1S	0.96
C9A—H9A	0.93	C1S—N1S	1.152 (13)
C8A—C7A	1.392 (7)
N2A—Ru—N2	96.95 (13)	C7A—C6A—C5A	123.4 (4)
N2A—Ru—N1A	78.94 (12)	N1A—C5A—C4A	121.6 (4)
N2—Ru—N1A	173.63 (13)	N1A—C5A—C6A	114.8 (3)
N2A—Ru—N1	87.84 (12)	C4A—C5A—C6A	123.5 (4)
N2—Ru—N1	79.24 (13)	C5A—C4A—C3A	119.4 (4)
N1A—Ru—N1	95.66 (12)	C5A—C4A—H4A3	120.3
N2A—Ru—N3	175.56 (12)	C3A—C4A—H4A3	120.3
N2—Ru—N3	86.83 (12)	C2A—C3A—C4A	118.9 (4)
N1A—Ru—N3	97.09 (12)	C2A—C3A—H3A	120.6
N1—Ru—N3	90.57 (12)	C4A—C3A—H3A	120.6
N2A—Ru—N3A	90.07 (12)	C3A—C2A—C1A	119.3 (4)
N2—Ru—N3A	98.16 (12)	C3A—C2A—H2A	120.3
N1A—Ru—N3A	86.77 (12)	C1A—C2A—H2A	120.3
N1—Ru—N3A	176.43 (11)	N1A—C1A—C2A	123.2 (4)
N3—Ru—N3A	91.72 (12)	N1A—C1A—H1A	118.4
C1—N1—C5	117.9 (4)	C2A—C1A—H1A	118.4
C1—N1—Ru	126.0 (3)	N3—C11—C12	123.0 (4)
C5—N1—Ru	116.0 (3)	N3—C11—H11	118.5
C10—N2—C6	116.5 (4)	C12—C11—H11	118.5
C10—N2—Ru	128.8 (3)	C11—C12—C13	119.5 (4)
C6—N2—Ru	114.7 (3)	C11—C12—H12	120.2
C10A—N2A—C6A	118.3 (4)	C13—C12—H12	120.2
C10A—N2A—Ru	125.7 (3)	C14—C13—N4	122.4 (5)
C6A—N2A—Ru	116.0 (3)	C14—C13—C12	117.4 (4)
C1A—N1A—C5A	117.4 (3)	N4—C13—C12	120.2 (5)
C1A—N1A—Ru	127.5 (3)	C13—C14—C15	119.5 (4)
C5A—N1A—Ru	114.9 (2)	C13—C14—H14	120.3
C15—N3—C11	116.2 (4)	C15—C14—H14	120.3
C15—N3—Ru	122.6 (3)	N3—C15—C14	124.4 (4)
C11—N3—Ru	121.0 (3)	N3—C15—H15	117.8
C13—N4—H4A	120	C14—C15—H15	117.8
C13—N4—H4B	120	N3A—C11A—C12A	124.6 (4)
H4A—N4—H4B	120	N3A—C11A—H11A	117.7
C11A—N3A—C15A	114.8 (3)	C12A—C11A—H11A	117.7
C11A—N3A—Ru	122.7 (3)	C11A—C12A—C13A	119.5 (4)
C15A—N3A—Ru	122.1 (3)	C11A—C12A—H12A	120.2
C13A—N4A—H4A1	120	C13A—C12A—H12A	120.2
C13A—N4A—H4A2	120	N4A—C13A—C14A	122.8 (4)
H4A1—N4A—H4A2	120	N4A—C13A—C12A	120.9 (4)
N1—C1—C2	122.9 (5)	C14A—C13A—C12A	116.4 (4)
N1—C1—H1	118.5	C15A—C14A—C13A	120.6 (4)
C2—C1—H1	118.5	C15A—C14A—H14A	119.7
C3—C2—C1	118.9 (5)	C13A—C14A—H14A	119.7
C3—C2—H2	120.5	N3A—C15A—C14A	124.0 (4)
C1—C2—H2	120.5	N3A—C15A—H15A	118
C2—C3—C4	119.0 (5)	C14A—C15A—H15A	118
C2—C3—H3	120.5	F1—P1—F3	177.6 (4)
C4—C3—H3	120.5	F1—P1—F6	93.1 (4)
C5—C4—C3	120.0 (5)	F3—P1—F6	89.1 (4)
C5—C4—H4	120	F1—P1—F5	88.2 (3)
C3—C4—H4	120	F3—P1—F5	89.7 (3)
N1—C5—C4	121.2 (4)	F6—P1—F5	177.5 (3)
N1—C5—C6	114.5 (3)	F1—P1—F4	88.0 (3)
C4—C5—C6	124.2 (4)	F3—P1—F4	93.1 (4)
N2—C6—C7	121.2 (4)	F6—P1—F4	90.4 (3)
N2—C6—C5	115.4 (3)	F5—P1—F4	87.5 (3)
C7—C6—C5	123.4 (4)	F1—P1—F2	90.2 (3)
C8—C7—C6	119.3 (5)	F3—P1—F2	88.7 (3)
C8—C7—H7	120.3	F6—P1—F2	89.7 (2)
C6—C7—H7	120.3	F5—P1—F2	92.4 (3)
C9—C8—C7	119.2 (5)	F4—P1—F2	178.2 (3)
C9—C8—H8	120.4	F1A—P1A—F4A	91.9 (3)
C7—C8—H8	120.4	F1A—P1A—F5A	88.0 (3)
C8—C9—C10	119.6 (5)	F4A—P1A—F5A	89.8 (2)
C8—C9—H9	120.2	F1A—P1A—F3A	93.4 (3)
C10—C9—H9	120.2	F4A—P1A—F3A	92.3 (3)
N2—C10—C9	124.2 (5)	F5A—P1A—F3A	177.5 (3)
N2—C10—H10	117.9	F1A—P1A—F2A	91.8 (3)
C9—C10—H10	117.9	F4A—P1A—F2A	176.1 (3)
N2A—C10A—C9A	121.7 (4)	F5A—P1A—F2A	89.1 (2)
N2A—C10A—H10A	119.2	F3A—P1A—F2A	88.7 (2)
C9A—C10A—H10A	119.2	F1A—P1A—F6A	178.6 (3)
C8A—C9A—C10A	120.1 (5)	F4A—P1A—F6A	87.1 (3)
C8A—C9A—H9A	120	F5A—P1A—F6A	91.1 (2)
C10A—C9A—H9A	120	F3A—P1A—F6A	87.6 (2)
C9A—C8A—C7A	119.2 (5)	F2A—P1A—F6A	89.2 (2)
C9A—C8A—H8A	120.4	C1S—C2S—H3S	109.5
C7A—C8A—H8A	120.4	C1S—C2S—H2S	109.5
C6A—C7A—C8A	118.9 (5)	H3S—C2S—H2S	109.5
C6A—C7A—H7A	120.6	C1S—C2S—H1S	109.5
C8A—C7A—H7A	120.6	H3S—C2S—H1S	109.5
N2A—C6A—C7A	121.8 (4)	H2S—C2S—H1S	109.5
N2A—C6A—C5A	114.8 (4)	N1S—C1S—C2S	175.7 (10)
N2A—Ru—N1—C1	81.4 (3)	Ru—N2—C6—C7	179.7 (3)
N2—Ru—N1—C1	178.9 (4)	C10—N2—C6—C5	179.1 (4)
N1A—Ru—N1—C1	2.8 (3)	Ru—N2—C6—C5	−0.2 (4)
N3—Ru—N1—C1	−94.4 (3)	N1—C5—C6—N2	2.2 (5)
N2A—Ru—N1—C5	−95.1 (3)	C4—C5—C6—N2	−177.4 (4)
N2—Ru—N1—C5	2.4 (3)	N1—C5—C6—C7	−177.6 (4)
N1A—Ru—N1—C5	−173.7 (3)	C4—C5—C6—C7	2.7 (7)
N3—Ru—N1—C5	89.1 (3)	N2—C6—C7—C8	0.9 (7)
N2A—Ru—N2—C10	−93.8 (4)	C5—C6—C7—C8	−179.3 (5)
N1—Ru—N2—C10	179.7 (4)	C6—C7—C8—C9	−0.9 (9)
N3—Ru—N2—C10	88.5 (4)	C7—C8—C9—C10	1.0 (10)
N3A—Ru—N2—C10	−2.7 (4)	C6—N2—C10—C9	1.3 (7)
N2A—Ru—N2—C6	85.3 (3)	Ru—N2—C10—C9	−179.6 (4)
N1—Ru—N2—C6	−1.1 (3)	C8—C9—C10—N2	−1.3 (9)
N3—Ru—N2—C6	−92.3 (3)	C6A—N2A—C10A—C9A	−1.4 (6)
N3A—Ru—N2—C6	176.4 (3)	Ru—N2A—C10A—C9A	−179.7 (4)
N2—Ru—N2A—C10A	7.0 (4)	N2A—C10A—C9A—C8A	−0.6 (8)
N1A—Ru—N2A—C10A	−177.9 (4)	C10A—C9A—C8A—C7A	2.1 (9)
N1—Ru—N2A—C10A	85.9 (3)	C9A—C8A—C7A—C6A	−1.5 (9)
N3A—Ru—N2A—C10A	−91.2 (3)	C10A—N2A—C6A—C7A	2.0 (6)
N2—Ru—N2A—C6A	−171.3 (3)	Ru—N2A—C6A—C7A	−179.6 (4)
N1A—Ru—N2A—C6A	3.8 (3)	C10A—N2A—C6A—C5A	−179.2 (4)
N1—Ru—N2A—C6A	−92.4 (3)	Ru—N2A—C6A—C5A	−0.7 (4)
N3A—Ru—N2A—C6A	90.5 (3)	C8A—C7A—C6A—N2A	−0.5 (8)
N2A—Ru—N1A—C1A	177.3 (3)	C8A—C7A—C6A—C5A	−179.3 (5)
N1—Ru—N1A—C1A	−96.0 (3)	C1A—N1A—C5A—C4A	3.0 (6)
N3—Ru—N1A—C1A	−4.7 (3)	Ru—N1A—C5A—C4A	−173.7 (3)
N3A—Ru—N1A—C1A	86.6 (3)	C1A—N1A—C5A—C6A	−175.4 (4)
N2A—Ru—N1A—C5A	−6.4 (3)	Ru—N1A—C5A—C6A	7.9 (4)
N1—Ru—N1A—C5A	80.3 (3)	N2A—C6A—C5A—N1A	−4.7 (5)
N3—Ru—N1A—C5A	171.6 (3)	C7A—C6A—C5A—N1A	174.1 (4)
N3A—Ru—N1A—C5A	−97.1 (3)	N2A—C6A—C5A—C4A	176.9 (4)
N2—Ru—N3—C15	121.1 (3)	C7A—C6A—C5A—C4A	−4.3 (7)
N1A—Ru—N3—C15	−53.9 (3)	N1A—C5A—C4A—C3A	−1.4 (7)
N1—Ru—N3—C15	41.9 (3)	C6A—C5A—C4A—C3A	176.9 (4)
N3A—Ru—N3—C15	−140.8 (3)	C5A—C4A—C3A—C2A	−1.7 (8)
N2—Ru—N3—C11	−54.3 (3)	C4A—C3A—C2A—C1A	3.0 (8)
N1A—Ru—N3—C11	130.7 (3)	C5A—N1A—C1A—C2A	−1.7 (6)
N1—Ru—N3—C11	−133.5 (3)	Ru—N1A—C1A—C2A	174.6 (3)
N3A—Ru—N3—C11	43.8 (3)	C3A—C2A—C1A—N1A	−1.3 (7)
N2A—Ru—N3A—C11A	37.0 (3)	C15—N3—C11—C12	−0.4 (6)
N2—Ru—N3A—C11A	−60.1 (3)	Ru—N3—C11—C12	175.3 (4)
N1A—Ru—N3A—C11A	115.9 (3)	N3—C11—C12—C13	0.4 (7)
N3—Ru—N3A—C11A	−147.1 (3)	C11—C12—C13—C14	0.0 (7)
N2A—Ru—N3A—C15A	−135.8 (3)	C11—C12—C13—N4	179.1 (4)
N2—Ru—N3A—C15A	127.2 (3)	N4—C13—C14—C15	−179.4 (4)
N1A—Ru—N3A—C15A	−56.9 (3)	C12—C13—C14—C15	−0.3 (7)
N3—Ru—N3A—C15A	40.1 (3)	C11—N3—C15—C14	0.1 (6)
C5—N1—C1—C2	0.5 (6)	Ru—N3—C15—C14	−175.5 (3)
Ru—N1—C1—C2	−176.0 (4)	C13—C14—C15—N3	0.3 (7)
N1—C1—C2—C3	0.4 (8)	C15A—N3A—C11A—C12A	0.6 (6)
C1—C2—C3—C4	−1.4 (8)	Ru—N3A—C11A—C12A	−172.6 (3)
C2—C3—C4—C5	1.6 (8)	N3A—C11A—C12A—C13A	0.5 (7)
C1—N1—C5—C4	−0.3 (6)	C11A—C12A—C13A—N4A	178.4 (5)
Ru—N1—C5—C4	176.5 (3)	C11A—C12A—C13A—C14A	−1.8 (7)
C1—N1—C5—C6	−180.0 (4)	N4A—C13A—C14A—C15A	−178.2 (5)
Ru—N1—C5—C6	−3.2 (4)	C12A—C13A—C14A—C15A	2.1 (7)
C3—C4—C5—N1	−0.7 (7)	C11A—N3A—C15A—C14A	−0.4 (6)
C3—C4—C5—C6	178.9 (5)	Ru—N3A—C15A—C14A	172.9 (3)
C10—N2—C6—C7	−1.1 (6)	C13A—C14A—C15A—N3A	−1.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···F4i	0.86	2.19	2.871 (8)	135
N4—H4B···F6Aii	0.86	2.47	2.962 (7)	117
N4A—H4A1···F5iii	0.86	2.44	3.184 (8)	145
N4A—H4A2···N1Siv	0.86	2.34	3.162 (13)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯F4i	0.86	2.19	2.871 (8)	135
N4—H4B⋯F6A ii	0.86	2.47	2.962 (7)	117
N4A—H4A1⋯F5iii	0.86	2.44	3.184 (8)	145
N4A—H4A2⋯N1S iv	0.86	2.34	3.162 (13)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .