cis-Bis(1,10-phenanthroline-κ(2)N,N')bis-(pyridin-4-amine-κN(1))ruthenium(II) bis-(hexa-fluoridophosphate).

In the title complex, [Ru(C(12)H(8)N(2))(2)(C(5)H(6)N(2))(2)](PF(6))(2), the Ru(II) atom is bonded to two α-diimine ligands, viz. 1,10-phenanthroline (phen), in a cis configuration, in addition with with two 4-amino-pyridine (4Apy) ligands, resulting in a distorted octa-hedral coordination geometry. N-H⋯F hydrogen-bonding inter-actions play an important role in the crystal assembly: 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. N-H⋯π contacts (H⋯centroid = 3.45 Å) are responsible for cross-linking between the helical chains along [001].

Related literature

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

Experimental

Crystal data

[Ru(C12H8N2)2(C5H6N2)2](PF6)2

M = 939.65

Orthorhombic,

a = 13.0943 (3) Å

b = 14.5730 (3) Å

c = 19.9366 (5) Å

V = 3804.37 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 298 K

0.40 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: Gaussian (Coppens et al., 1965 ▶) T min = 0.699, T max = 0.938

29253 measured reflections

6964 independent reflections

5348 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.151

S = 1.04

6964 reflections

514 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.48 e Å−3

Absolute structure: Flack (1983 ▶), 3264 Friedel pairs

Flack parameter: 0.25 (6)

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/S1600536812051999/bg2495sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051999/bg2495Isup2.hkl

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

[Ru(C12H8N2)2(C5H6N2)2](PF6)2	F(000) = 1880
Mr = 939.65	Dx = 1.641 Mg m−3
Orthorhombic, P21cn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2n 2a	Cell parameters from 35299 reflections
a = 13.0943 (3) Å	θ = 2.9–25.7°
b = 14.5730 (3) Å	µ = 0.59 mm−1
c = 19.9366 (5) Å	T = 298 K
V = 3804.37 (15) Å3	Prism, red
Z = 4	0.40 × 0.20 × 0.10 mm

Nonius KappaCCD diffractometer	5348 reflections with I > 2σ(I)
CCD scans	Rint = 0.066
Absorption correction: gaussian (Coppens et al., 1965)	θmax = 25.7°, θmin = 2.9°
Tmin = 0.699, Tmax = 0.938	h = −15→15
29253 measured reflections	k = −17→17
6964 independent reflections	l = −24→24

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0819P)2 + 2.252P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.053	(Δ/σ)max = 0.001
wR(F2) = 0.151	Δρmax = 0.39 e Å−3
S = 1.04	Δρmin = −0.48 e Å−3
6964 reflections	Absolute structure: Flack (1983), 3264 Friedel pairs
514 parameters	Flack parameter: 0.25 (6)
1 restraint

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.

	x	y	z	Uiso*/Ueq
Ru1	0.15387 (9)	0.53833 (3)	0.74946 (2)	0.05771 (15)
P1A	−0.07388 (19)	0.48572 (17)	1.00634 (11)	0.0984 (7)
P1	0.80453 (18)	0.52929 (14)	0.54965 (10)	0.0872 (5)
N3A	0.1641 (4)	0.6513 (3)	0.6842 (2)	0.0607 (11)
N1	0.1410 (4)	0.4247 (3)	0.8099 (2)	0.0702 (12)
N1A	0.1800 (3)	0.6329 (3)	0.8261 (2)	0.0623 (13)
F3	0.9191 (5)	0.5450 (5)	0.5394 (5)	0.185 (4)
N3	0.3077 (4)	0.5015 (3)	0.7311 (2)	0.0581 (10)
C13A	0.0842 (5)	0.6831 (4)	0.6485 (4)	0.0740 (16)
H13A	0.0243	0.6488	0.6486	0.089*
C11A	−0.0013 (5)	0.6384 (4)	0.8232 (3)	0.0651 (14)
C11	0.0970 (5)	0.3550 (4)	0.7056 (3)	0.0714 (15)
C7A	−0.0949 (5)	0.6733 (5)	0.8473 (3)	0.0816 (18)
C12A	0.0923 (5)	0.6686 (4)	0.8520 (3)	0.0659 (14)
F6	0.8266 (5)	0.4546 (3)	0.6050 (3)	0.1222 (17)
C6A	−0.0927 (7)	0.7386 (5)	0.8989 (4)	0.094 (2)
H6A	−0.1547	0.762	0.9139	0.112*
C17A	0.2501 (5)	0.7059 (4)	0.6828 (4)	0.0773 (17)
H17A	0.3069	0.6883	0.7078	0.093*
C4A	0.0903 (6)	0.7348 (4)	0.9049 (3)	0.0729 (16)
C12	0.1115 (5)	0.3467 (4)	0.7771 (4)	0.0769 (17)
F1	0.7817 (4)	0.6041 (5)	0.4944 (3)	0.150 (3)
C5A	−0.0065 (6)	0.7699 (5)	0.9284 (4)	0.088 (2)
H5A	−0.0095	0.8127	0.9629	0.105*
C1	0.1573 (7)	0.4181 (5)	0.8760 (3)	0.0878 (18)
H1	0.1749	0.4706	0.8999	0.105*
C2A	0.2720 (6)	0.7330 (5)	0.9000 (4)	0.095 (2)
H2A	0.3347	0.7555	0.9145	0.115*
C14A	0.0856 (6)	0.7631 (5)	0.6119 (3)	0.0773 (17)
H14A	0.0282	0.7805	0.5876	0.093*
C9	0.0738 (5)	0.3750 (6)	0.5722 (4)	0.091 (2)
H9	0.0674	0.3827	0.5261	0.109*
N2A	0.0059 (4)	0.5751 (4)	0.7731 (2)	0.0637 (11)
F2	0.8036 (11)	0.4537 (5)	0.4968 (3)	0.214 (5)
C15A	0.1706 (7)	0.8169 (5)	0.6111 (3)	0.090 (2)
C9A	−0.1744 (6)	0.5747 (8)	0.7679 (5)	0.107 (3)
H9A	−0.2332	0.552	0.7477	0.128*
F5	0.6885 (5)	0.5172 (7)	0.5623 (5)	0.210 (4)
N2	0.1136 (4)	0.4397 (4)	0.6788 (3)	0.0670 (12)
F4	0.8079 (10)	0.6051 (5)	0.6041 (4)	0.216 (4)
C1A	0.2674 (6)	0.6659 (5)	0.8500 (3)	0.0759 (18)
H1A	0.3283	0.6433	0.8325	0.091*
C3A	0.1856 (6)	0.7641 (5)	0.9268 (4)	0.087 (2)
H3A	0.1892	0.8069	0.9613	0.105*
N4A	0.1747 (7)	0.8976 (5)	0.5778 (4)	0.140 (3)
H4A1	0.1223	0.9169	0.556	0.167*
H4A2	0.2298	0.9298	0.5785	0.167*
C8A	−0.1830 (6)	0.6385 (6)	0.8176 (4)	0.096 (2)
H8A	−0.247	0.6585	0.8316	0.115*
C16A	0.2548 (6)	0.7859 (5)	0.6457 (4)	0.088 (2)
H16A	0.3154	0.819	0.6441	0.106*
C4	0.0975 (6)	0.2625 (5)	0.8085 (5)	0.101 (3)
C3	0.1177 (8)	0.2590 (7)	0.8792 (5)	0.117 (3)
H3	0.1094	0.2046	0.903	0.14*
C10A	−0.0813 (6)	0.5436 (5)	0.7473 (3)	0.080 (2)
H10A	−0.0786	0.4989	0.7141	0.096*
C6	0.0501 (6)	0.1941 (6)	0.7015 (6)	0.101 (3)
H6	0.0289	0.1434	0.6769	0.121*
C5	0.0644 (7)	0.1858 (6)	0.7664 (7)	0.118 (3)
H5	0.0531	0.129	0.7864	0.141*
C10	0.1018 (5)	0.4487 (5)	0.6122 (3)	0.0739 (16)
H10	0.1126	0.5057	0.5925	0.089*
C2	0.1486 (10)	0.3352 (7)	0.9097 (4)	0.119 (3)
H2	0.1649	0.3329	0.9551	0.143*
C13	0.3510 (5)	0.5010 (4)	0.6701 (3)	0.0665 (14)
H13	0.3114	0.5193	0.6338	0.08*
C17	0.3694 (5)	0.4711 (4)	0.7810 (4)	0.0706 (15)
H17	0.3423	0.4695	0.8241	0.085*
C15	0.5118 (5)	0.4449 (4)	0.7086 (3)	0.0720 (16)
C16	0.4683 (5)	0.4424 (5)	0.7732 (4)	0.0763 (17)
H16	0.506	0.4218	0.8098	0.092*
C14	0.4488 (5)	0.4756 (4)	0.6583 (3)	0.0748 (16)
H14	0.474	0.479	0.6148	0.09*
N4	0.6095 (5)	0.4218 (5)	0.6990 (3)	0.1020 (19)
H4A	0.6361	0.4258	0.6597	0.122*
H4B	0.6458	0.4029	0.7322	0.122*
C8	0.0556 (6)	0.2912 (7)	0.6005 (6)	0.112 (3)
H8	0.0357	0.2419	0.5739	0.134*
C7	0.0666 (5)	0.2803 (5)	0.6678 (5)	0.091 (2)
F1A	0.0196 (7)	0.5302 (7)	0.9756 (4)	0.208 (4)
F6A	−0.1797 (7)	0.4604 (5)	1.0366 (5)	0.171 (3)
F2A	−0.0723 (8)	0.5749 (5)	1.0464 (5)	0.220 (4)
F3A	−0.1282 (16)	0.5199 (11)	0.9488 (7)	0.419 (15)
F5A	−0.0223 (11)	0.4465 (7)	1.0632 (7)	0.289 (8)
F4A	−0.0741 (7)	0.3944 (6)	0.9729 (6)	0.237 (5)

	U11	U22	U33	U12	U13	U23
Ru1	0.0572 (2)	0.0581 (2)	0.0578 (2)	−0.0022 (3)	−0.00123 (18)	0.00524 (17)
P1A	0.1151 (19)	0.1057 (16)	0.0743 (11)	−0.0329 (15)	0.0118 (12)	0.0029 (11)
P1	0.0829 (12)	0.1037 (13)	0.0751 (11)	−0.0042 (11)	−0.0063 (10)	0.0133 (10)
N3A	0.061 (3)	0.068 (2)	0.054 (2)	−0.003 (3)	−0.006 (2)	0.0084 (18)
N1	0.068 (3)	0.072 (3)	0.071 (3)	−0.003 (3)	0.012 (3)	0.011 (2)
N1A	0.056 (3)	0.060 (3)	0.070 (3)	−0.001 (2)	−0.013 (2)	0.007 (2)
F3	0.082 (4)	0.187 (6)	0.287 (10)	−0.019 (4)	−0.017 (5)	0.113 (6)
N3	0.062 (3)	0.056 (3)	0.056 (2)	0.003 (2)	−0.002 (2)	0.002 (2)
C13A	0.067 (4)	0.070 (4)	0.085 (4)	−0.001 (3)	−0.012 (3)	0.006 (3)
C11A	0.071 (4)	0.068 (3)	0.056 (3)	−0.003 (3)	0.003 (3)	0.007 (3)
C11	0.056 (3)	0.063 (3)	0.096 (4)	−0.003 (3)	0.015 (3)	−0.003 (3)
C7A	0.077 (4)	0.088 (4)	0.080 (4)	0.013 (3)	0.013 (3)	0.001 (3)
C12A	0.067 (4)	0.069 (3)	0.062 (3)	0.001 (3)	−0.009 (3)	0.009 (3)
F6	0.146 (5)	0.115 (4)	0.106 (3)	−0.005 (3)	−0.021 (3)	0.023 (3)
C6A	0.098 (6)	0.085 (5)	0.098 (5)	0.019 (4)	0.023 (5)	0.000 (4)
C17A	0.067 (4)	0.073 (4)	0.092 (5)	−0.008 (3)	0.006 (3)	0.023 (3)
C4A	0.094 (5)	0.066 (3)	0.059 (3)	0.001 (3)	−0.001 (3)	−0.004 (3)
C12	0.063 (3)	0.062 (3)	0.106 (5)	0.002 (3)	0.026 (4)	0.010 (4)
F1	0.109 (4)	0.184 (5)	0.158 (5)	−0.041 (4)	−0.049 (3)	0.096 (4)
C5A	0.103 (6)	0.081 (4)	0.080 (4)	0.015 (4)	0.007 (4)	−0.002 (3)
C1	0.098 (5)	0.094 (4)	0.072 (4)	0.022 (5)	0.024 (4)	0.022 (3)
C2A	0.081 (5)	0.095 (5)	0.111 (6)	−0.012 (4)	−0.007 (4)	−0.010 (4)
C14A	0.082 (4)	0.090 (4)	0.061 (3)	0.017 (4)	0.001 (3)	0.014 (3)
C9	0.066 (4)	0.116 (6)	0.090 (5)	−0.002 (4)	−0.004 (3)	−0.043 (4)
N2A	0.060 (3)	0.075 (3)	0.057 (2)	−0.002 (2)	−0.003 (2)	0.003 (2)
F2	0.405 (16)	0.149 (6)	0.087 (4)	−0.094 (7)	0.001 (6)	−0.025 (4)
C15A	0.103 (6)	0.085 (4)	0.082 (4)	0.011 (4)	0.008 (4)	0.030 (3)
C9A	0.062 (4)	0.155 (8)	0.103 (5)	−0.017 (5)	0.001 (4)	−0.027 (6)
F5	0.095 (4)	0.291 (10)	0.243 (8)	0.007 (5)	0.022 (5)	0.141 (8)
N2	0.054 (3)	0.071 (3)	0.076 (3)	−0.001 (2)	0.004 (2)	0.002 (2)
F4	0.362 (14)	0.132 (5)	0.155 (6)	0.047 (7)	−0.047 (7)	−0.028 (5)
C1A	0.079 (5)	0.076 (4)	0.073 (4)	−0.003 (3)	−0.013 (3)	−0.004 (3)
C3A	0.114 (7)	0.074 (4)	0.074 (4)	−0.008 (4)	−0.013 (4)	−0.014 (3)
N4A	0.125 (7)	0.123 (6)	0.170 (7)	0.009 (5)	0.004 (5)	0.077 (5)
C8A	0.070 (4)	0.129 (6)	0.089 (5)	0.017 (4)	0.008 (4)	−0.012 (5)
C16A	0.085 (5)	0.072 (4)	0.109 (5)	0.000 (4)	0.012 (4)	0.017 (4)
C4	0.086 (5)	0.066 (4)	0.150 (8)	−0.007 (4)	0.041 (5)	0.015 (4)
C3	0.134 (8)	0.102 (6)	0.114 (6)	0.008 (5)	0.033 (5)	0.056 (5)
C10A	0.060 (4)	0.099 (6)	0.080 (5)	−0.005 (3)	−0.006 (3)	−0.015 (3)
C6	0.084 (5)	0.074 (5)	0.144 (8)	−0.011 (4)	0.029 (5)	−0.015 (5)
C5	0.106 (7)	0.059 (4)	0.187 (10)	−0.017 (4)	0.056 (7)	0.001 (6)
C10	0.074 (4)	0.084 (4)	0.063 (3)	−0.002 (3)	0.001 (3)	−0.010 (3)
C2	0.151 (8)	0.112 (6)	0.095 (5)	0.009 (7)	0.032 (6)	0.044 (5)
C13	0.068 (4)	0.073 (4)	0.059 (3)	−0.009 (3)	0.005 (3)	−0.006 (3)
C17	0.070 (4)	0.078 (4)	0.064 (4)	0.005 (3)	0.000 (3)	0.006 (3)
C15	0.067 (4)	0.066 (3)	0.083 (4)	0.001 (3)	0.002 (3)	−0.009 (3)
C16	0.065 (4)	0.072 (4)	0.093 (4)	0.010 (3)	−0.002 (3)	0.002 (3)
C14	0.081 (4)	0.075 (4)	0.068 (4)	−0.005 (3)	0.006 (3)	−0.019 (3)
N4	0.078 (4)	0.130 (5)	0.098 (4)	0.013 (4)	0.008 (3)	−0.024 (4)
C8	0.065 (4)	0.106 (6)	0.164 (9)	−0.008 (4)	−0.008 (5)	−0.075 (7)
C7	0.050 (4)	0.076 (4)	0.147 (8)	−0.005 (3)	0.006 (4)	−0.031 (5)
F1A	0.162 (7)	0.296 (11)	0.167 (7)	−0.117 (7)	0.074 (6)	−0.047 (6)
F6A	0.150 (6)	0.179 (7)	0.184 (7)	−0.042 (4)	0.052 (6)	0.002 (5)
F2A	0.199 (8)	0.173 (6)	0.289 (10)	−0.035 (6)	−0.024 (8)	−0.118 (7)
F3A	0.54 (3)	0.429 (19)	0.291 (13)	−0.312 (19)	−0.279 (17)	0.282 (14)
F5A	0.361 (17)	0.187 (7)	0.320 (14)	−0.075 (8)	−0.219 (13)	0.112 (8)
F4A	0.174 (7)	0.205 (7)	0.333 (12)	−0.027 (6)	0.088 (8)	−0.153 (8)

Ru1—N1	2.054 (5)	C1—H1	0.93
Ru1—N2A	2.065 (5)	C2A—C3A	1.330 (10)
Ru1—N2	2.081 (5)	C2A—C1A	1.399 (10)
Ru1—N1A	2.086 (5)	C2A—H2A	0.93
Ru1—N3A	2.103 (4)	C14A—C15A	1.361 (11)
Ru1—N3	2.117 (5)	C14A—H14A	0.93
P1A—F5A	1.438 (9)	C9—C8	1.367 (13)
P1A—F3A	1.439 (9)	C9—C10	1.386 (9)
P1A—F4A	1.488 (7)	C9—H9	0.93
P1A—F1A	1.515 (7)	N2A—C10A	1.334 (9)
P1A—F2A	1.526 (7)	C15A—N4A	1.353 (9)
P1A—F6A	1.556 (8)	C15A—C16A	1.377 (11)
P1—F2	1.525 (6)	C9A—C8A	1.363 (12)
P1—F3	1.531 (7)	C9A—C10A	1.364 (12)
P1—F4	1.549 (7)	C9A—H9A	0.93
P1—F5	1.550 (7)	N2—C10	1.342 (8)
P1—F6	1.577 (5)	C1A—H1A	0.93
P1—F1	1.579 (5)	C3A—H3A	0.93
N3A—C13A	1.347 (8)	N4A—H4A1	0.86
N3A—C17A	1.379 (8)	N4A—H4A2	0.86
N1—C1	1.338 (8)	C8A—H8A	0.93
N1—C12	1.367 (8)	C16A—H16A	0.93
N1A—C1A	1.329 (8)	C4—C3	1.435 (14)
N1A—C12A	1.363 (8)	C4—C5	1.464 (13)
N3—C13	1.341 (7)	C3—C2	1.331 (13)
N3—C17	1.355 (8)	C3—H3	0.93
C13A—C14A	1.375 (9)	C10A—H10A	0.93
C13A—H13A	0.93	C6—C5	1.312 (14)
C11A—N2A	1.364 (8)	C6—C7	1.442 (12)
C11A—C7A	1.411 (9)	C6—H6	0.93
C11A—C12A	1.423 (9)	C5—H5	0.93
C11—N2	1.363 (8)	C10—H10	0.93
C11—C7	1.383 (10)	C2—H2	0.93
C11—C12	1.442 (11)	C13—C14	1.353 (9)
C7A—C8A	1.392 (10)	C13—H13	0.93
C7A—C6A	1.402 (10)	C17—C16	1.370 (9)
C12A—C4A	1.430 (9)	C17—H17	0.93
C6A—C5A	1.351 (11)	C15—N4	1.336 (10)
C6A—H6A	0.93	C15—C14	1.373 (10)
C17A—C16A	1.382 (9)	C15—C16	1.410 (10)
C17A—H17A	0.93	C16—H16	0.93
C4A—C3A	1.389 (11)	C14—H14	0.93
C4A—C5A	1.446 (10)	N4—H4A	0.86
C12—C4	1.389 (9)	N4—H4B	0.86
C5A—H5A	0.93	C8—C7	1.358 (13)
C1—C2	1.388 (10)	C8—H8	0.93
N1—Ru1—N2A	89.9 (2)	C4A—C5A—H5A	120.9
N1—Ru1—N2	79.6 (2)	N1—C1—C2	121.8 (8)
N2A—Ru1—N2	95.5 (2)	N1—C1—H1	119.1
N1—Ru1—N1A	96.70 (19)	C2—C1—H1	119.1
N2A—Ru1—N1A	79.39 (19)	C3A—C2A—C1A	119.2 (7)
N2—Ru1—N1A	173.76 (19)	C3A—C2A—H2A	120.4
N1—Ru1—N3A	177.5 (2)	C1A—C2A—H2A	120.4
N2A—Ru1—N3A	89.9 (2)	C15A—C14A—C13A	120.3 (6)
N2—Ru1—N3A	97.90 (18)	C15A—C14A—H14A	119.8
N1A—Ru1—N3A	85.74 (18)	C13A—C14A—H14A	119.8
N1—Ru1—N3	88.6 (2)	C8—C9—C10	120.1 (8)
N2A—Ru1—N3	176.74 (18)	C8—C9—H9	120
N2—Ru1—N3	87.06 (19)	C10—C9—H9	120
N1A—Ru1—N3	97.92 (18)	C10A—N2A—C11A	117.1 (6)
N3A—Ru1—N3	91.8 (2)	C10A—N2A—Ru1	128.8 (4)
F5A—P1A—F3A	176.7 (7)	C11A—N2A—Ru1	114.0 (4)
F5A—P1A—F4A	90.0 (7)	N4A—C15A—C14A	122.7 (8)
F3A—P1A—F4A	87.2 (9)	N4A—C15A—C16A	119.9 (8)
F5A—P1A—F1A	96.3 (8)	C14A—C15A—C16A	117.4 (6)
F3A—P1A—F1A	85.9 (8)	C8A—C9A—C10A	121.3 (7)
F4A—P1A—F1A	101.7 (5)	C8A—C9A—H9A	119.4
F5A—P1A—F2A	85.4 (7)	C10A—C9A—H9A	119.4
F3A—P1A—F2A	97.4 (9)	C10—N2—C11	117.3 (6)
F4A—P1A—F2A	175.1 (7)	C10—N2—Ru1	129.2 (4)
F1A—P1A—F2A	80.6 (5)	C11—N2—Ru1	113.6 (4)
F5A—P1A—F6A	91.1 (8)	N1A—C1A—C2A	123.0 (7)
F3A—P1A—F6A	87.2 (9)	N1A—C1A—H1A	118.5
F4A—P1A—F6A	87.7 (4)	C2A—C1A—H1A	118.5
F1A—P1A—F6A	168.0 (6)	C2A—C3A—C4A	122.2 (7)
F2A—P1A—F6A	90.6 (5)	C2A—C3A—H3A	118.9
F2—P1—F3	91.3 (6)	C4A—C3A—H3A	118.9
F2—P1—F4	178.6 (7)	C15A—N4A—H4A1	120
F3—P1—F4	87.7 (6)	C15A—N4A—H4A2	120
F2—P1—F5	91.3 (7)	H4A1—N4A—H4A2	120
F3—P1—F5	177.4 (6)	C9A—C8A—C7A	119.3 (7)
F4—P1—F5	89.7 (7)	C9A—C8A—H8A	120.4
F2—P1—F6	89.2 (4)	C7A—C8A—H8A	120.4
F3—P1—F6	91.0 (3)	C15A—C16A—C17A	120.6 (7)
F4—P1—F6	89.8 (4)	C15A—C16A—H16A	119.7
F5—P1—F6	89.3 (4)	C17A—C16A—H16A	119.7
F2—P1—F1	90.8 (4)	C12—C4—C3	116.7 (8)
F3—P1—F1	89.4 (3)	C12—C4—C5	117.1 (9)
F4—P1—F1	90.1 (4)	C3—C4—C5	126.1 (8)
F5—P1—F1	90.3 (3)	C2—C3—C4	118.4 (7)
F6—P1—F1	179.6 (4)	C2—C3—H3	120.8
C13A—N3A—C17A	115.2 (5)	C4—C3—H3	120.8
C13A—N3A—Ru1	123.2 (4)	N2A—C10A—C9A	122.3 (7)
C17A—N3A—Ru1	121.0 (4)	N2A—C10A—H10A	118.8
C1—N1—C12	117.1 (6)	C9A—C10A—H10A	118.8
C1—N1—Ru1	128.5 (5)	C5—C6—C7	121.3 (8)
C12—N1—Ru1	114.4 (4)	C5—C6—H6	119.4
C1A—N1A—C12A	116.9 (5)	C7—C6—H6	119.4
C1A—N1A—Ru1	130.0 (4)	C6—C5—C4	122.5 (8)
C12A—N1A—Ru1	113.0 (4)	C6—C5—H5	118.8
C13—N3—C17	114.2 (6)	C4—C5—H5	118.8
C13—N3—Ru1	124.1 (4)	N2—C10—C9	121.6 (7)
C17—N3—Ru1	121.6 (4)	N2—C10—H10	119.2
N3A—C13A—C14A	124.2 (6)	C9—C10—H10	119.2
N3A—C13A—H13A	117.9	C3—C2—C1	122.0 (8)
C14A—C13A—H13A	117.9	C3—C2—H2	119
N2A—C11A—C7A	123.6 (6)	C1—C2—H2	119
N2A—C11A—C12A	116.5 (6)	N3—C13—C14	124.0 (6)
C7A—C11A—C12A	119.9 (6)	N3—C13—H13	118
N2—C11—C7	123.0 (7)	C14—C13—H13	118
N2—C11—C12	116.3 (5)	N3—C17—C16	125.5 (7)
C7—C11—C12	120.7 (6)	N3—C17—H17	117.2
C8A—C7A—C6A	125.2 (7)	C16—C17—H17	117.2
C8A—C7A—C11A	116.3 (6)	N4—C15—C14	123.6 (7)
C6A—C7A—C11A	118.5 (7)	N4—C15—C16	120.7 (7)
N1A—C12A—C11A	117.1 (5)	C14—C15—C16	115.6 (6)
N1A—C12A—C4A	123.5 (6)	C17—C16—C15	118.5 (7)
C11A—C12A—C4A	119.4 (6)	C17—C16—H16	120.7
C5A—C6A—C7A	124.5 (7)	C15—C16—H16	120.7
C5A—C6A—H6A	117.8	C13—C14—C15	122.0 (6)
C7A—C6A—H6A	117.8	C13—C14—H14	119
N3A—C17A—C16A	122.2 (6)	C15—C14—H14	119
N3A—C17A—H17A	118.9	C15—N4—H4A	120
C16A—C17A—H17A	118.9	C15—N4—H4B	120
C3A—C4A—C12A	115.0 (7)	H4A—N4—H4B	120
C3A—C4A—C5A	125.3 (6)	C7—C8—C9	119.5 (7)
C12A—C4A—C5A	119.6 (7)	C7—C8—H8	120.2
N1—C12—C4	123.8 (8)	C9—C8—H8	120.2
N1—C12—C11	116.1 (5)	C8—C7—C11	118.5 (8)
C4—C12—C11	120.1 (7)	C8—C7—C6	123.1 (8)
C6A—C5A—C4A	118.1 (7)	C11—C7—C6	118.3 (9)
C6A—C5A—H5A	120.9
N2A—Ru1—N3A—C13A	−33.7 (5)	C12A—C11A—N2A—Ru1	−0.7 (6)
N2—Ru1—N3A—C13A	61.8 (5)	N1—Ru1—N2A—C10A	−81.1 (6)
N1A—Ru1—N3A—C13A	−113.1 (5)	N2—Ru1—N2A—C10A	−1.6 (6)
N3—Ru1—N3A—C13A	149.1 (5)	N1A—Ru1—N2A—C10A	−178.0 (6)
N2A—Ru1—N3A—C17A	136.6 (5)	N3A—Ru1—N2A—C10A	96.4 (6)
N2—Ru1—N3A—C17A	−127.9 (5)	N1—Ru1—N2A—C11A	97.0 (4)
N1A—Ru1—N3A—C17A	57.2 (5)	N2—Ru1—N2A—C11A	176.5 (4)
N3—Ru1—N3A—C17A	−40.6 (5)	N1A—Ru1—N2A—C11A	0.1 (4)
N2A—Ru1—N1—C1	−85.9 (7)	N3A—Ru1—N2A—C11A	−85.6 (4)
N2—Ru1—N1—C1	178.5 (7)	C13A—C14A—C15A—N4A	−177.8 (8)
N1A—Ru1—N1—C1	−6.6 (7)	C13A—C14A—C15A—C16A	2.7 (11)
N3—Ru1—N1—C1	91.2 (7)	C7—C11—N2—C10	−1.6 (9)
N2A—Ru1—N1—C12	93.8 (5)	C12—C11—N2—C10	179.2 (6)
N2—Ru1—N1—C12	−1.8 (4)	C7—C11—N2—Ru1	178.0 (5)
N1A—Ru1—N1—C12	173.1 (4)	C12—C11—N2—Ru1	−1.1 (6)
N3—Ru1—N1—C12	−89.1 (5)	N1—Ru1—N2—C10	−178.8 (6)
N1—Ru1—N1A—C1A	95.8 (6)	N2A—Ru1—N2—C10	92.3 (6)
N2A—Ru1—N1A—C1A	−175.5 (6)	N3A—Ru1—N2—C10	1.6 (6)
N3A—Ru1—N1A—C1A	−84.9 (5)	N3—Ru1—N2—C10	−89.7 (6)
N3—Ru1—N1A—C1A	6.3 (6)	N1—Ru1—N2—C11	1.6 (4)
N1—Ru1—N1A—C12A	−88.2 (4)	N2A—Ru1—N2—C11	−87.3 (4)
N2A—Ru1—N1A—C12A	0.5 (4)	N3A—Ru1—N2—C11	−178.0 (4)
N3A—Ru1—N1A—C12A	91.2 (4)	N3—Ru1—N2—C11	90.7 (4)
N3—Ru1—N1A—C12A	−177.6 (4)	C12A—N1A—C1A—C2A	1.0 (9)
N1—Ru1—N3—C13	134.1 (5)	Ru1—N1A—C1A—C2A	176.9 (5)
N2—Ru1—N3—C13	54.4 (5)	C3A—C2A—C1A—N1A	1.9 (12)
N1A—Ru1—N3—C13	−129.4 (5)	C1A—C2A—C3A—C4A	−2.5 (12)
N3A—Ru1—N3—C13	−43.4 (5)	C12A—C4A—C3A—C2A	0.4 (11)
N1—Ru1—N3—C17	−42.1 (5)	C5A—C4A—C3A—C2A	−175.7 (8)
N2—Ru1—N3—C17	−121.8 (5)	C10A—C9A—C8A—C7A	0.8 (14)
N1A—Ru1—N3—C17	54.4 (5)	C6A—C7A—C8A—C9A	−179.7 (8)
N3A—Ru1—N3—C17	140.4 (4)	C11A—C7A—C8A—C9A	−0.4 (11)
C17A—N3A—C13A—C14A	0.9 (10)	N4A—C15A—C16A—C17A	176.6 (7)
Ru1—N3A—C13A—C14A	171.7 (5)	C14A—C15A—C16A—C17A	−3.8 (12)
N2A—C11A—C7A—C8A	0.9 (9)	N3A—C17A—C16A—C15A	3.6 (11)
C12A—C11A—C7A—C8A	−178.4 (6)	N1—C12—C4—C3	−1.3 (11)
N2A—C11A—C7A—C6A	−179.7 (6)	C11—C12—C4—C3	177.3 (7)
C12A—C11A—C7A—C6A	1.0 (9)	N1—C12—C4—C5	179.2 (7)
C1A—N1A—C12A—C11A	175.6 (6)	C11—C12—C4—C5	−2.1 (10)
Ru1—N1A—C12A—C11A	−1.0 (6)	C12—C4—C3—C2	−0.3 (13)
C1A—N1A—C12A—C4A	−3.3 (8)	C5—C4—C3—C2	179.1 (9)
Ru1—N1A—C12A—C4A	−179.9 (5)	C11A—N2A—C10A—C9A	2.1 (11)
N2A—C11A—C12A—N1A	1.2 (8)	Ru1—N2A—C10A—C9A	−179.9 (7)
C7A—C11A—C12A—N1A	−179.5 (6)	C8A—C9A—C10A—N2A	−1.7 (14)
N2A—C11A—C12A—C4A	−179.9 (5)	C7—C6—C5—C4	0.2 (14)
C7A—C11A—C12A—C4A	−0.5 (9)	C12—C4—C5—C6	1.3 (13)
C8A—C7A—C6A—C5A	178.1 (8)	C3—C4—C5—C6	−178.1 (9)
C11A—C7A—C6A—C5A	−1.2 (11)	C11—N2—C10—C9	0.0 (9)
C13A—N3A—C17A—C16A	−2.0 (10)	Ru1—N2—C10—C9	−179.6 (5)
Ru1—N3A—C17A—C16A	−173.1 (5)	C8—C9—C10—N2	1.3 (11)
N1A—C12A—C4A—C3A	2.7 (9)	C4—C3—C2—C1	2.9 (17)
C11A—C12A—C4A—C3A	−176.2 (6)	N1—C1—C2—C3	−4.2 (16)
N1A—C12A—C4A—C5A	179.0 (6)	C17—N3—C13—C14	−2.1 (8)
C11A—C12A—C4A—C5A	0.2 (9)	Ru1—N3—C13—C14	−178.5 (5)
C1—N1—C12—C4	0.2 (10)	C13—N3—C17—C16	0.7 (9)
Ru1—N1—C12—C4	−179.5 (5)	Ru1—N3—C17—C16	177.3 (5)
C1—N1—C12—C11	−178.5 (6)	N3—C17—C16—C15	0.6 (10)
Ru1—N1—C12—C11	1.8 (7)	N4—C15—C16—C17	176.8 (7)
N2—C11—C12—N1	−0.5 (8)	C14—C15—C16—C17	−0.7 (9)
C7—C11—C12—N1	−179.6 (6)	N3—C13—C14—C15	2.1 (10)
N2—C11—C12—C4	−179.2 (6)	N4—C15—C14—C13	−178.0 (6)
C7—C11—C12—C4	1.6 (9)	C16—C15—C14—C13	−0.6 (9)
C7A—C6A—C5A—C4A	0.8 (12)	C10—C9—C8—C7	−1.0 (11)
C3A—C4A—C5A—C6A	175.6 (7)	C9—C8—C7—C11	−0.5 (11)
C12A—C4A—C5A—C6A	−0.3 (10)	C9—C8—C7—C6	−179.3 (7)
C12—N1—C1—C2	2.5 (12)	N2—C11—C7—C8	1.9 (10)
Ru1—N1—C1—C2	−177.9 (7)	C12—C11—C7—C8	−179.0 (6)
N3A—C13A—C14A—C15A	−1.4 (11)	N2—C11—C7—C6	−179.3 (6)
C7A—C11A—N2A—C10A	−1.7 (9)	C12—C11—C7—C6	−0.2 (9)
C12A—C11A—N2A—C10A	177.6 (6)	C5—C6—C7—C8	178.1 (8)
C7A—C11A—N2A—Ru1	179.9 (5)	C5—C6—C7—C11	−0.7 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···F5	0.86	2.45	3.231 (12)	151
N4A—H4A1···F1Ai	0.86	2.23	3.063 (12)	163
N4A—H4A2···F3Aii	0.86	2.34	3.18 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯F5	0.86	2.45	3.231 (12)	151
N4A—H4A1⋯F1A i	0.86	2.23	3.063 (12)	163
N4A—H4A2⋯F3A ii	0.86	2.34	3.18 (2)	165

Symmetry codes: (i) ; (ii) .