Bis(2,2':6',2''-terpyridine)-ruthenium(II) bis-(perchlorate) hemihydrate.

The asymmetric unit of the title compound, [Ru(C(15)H(11)N(3))(2)](ClO(4))(2)·0.5H(2)O, contains one ruthenium-terpiridine complex cation, two perchlorate anions and one half-mol-ecule of water. Face-to-face and face-to-edge π-stacking inter-actions between terpyridine units [centroid-centroid distances = 3.793 (2) and 3.801 (2)  Å] stabilize the crystal lattice The partially occupied water mol-ecule inter-acts with two perchlorate ions via O-H⋯O hydrogen bonds. In the crystal lattice, the complex cations, perchlorate ion-water pairs and the second perchlorate anions are arranged into columns along b direction.

Related literature

For the preparation of terpyridine complexes with transition metals, see: Burstall & Nyholm (1952 ▶). For the structures of salts of complexes of ruthenium with terpyridine, see: Craig et al. (1998 ▶); Lashgari et al. (1999 ▶); Pyo et al. (1999 ▶); Tovee et al. (2009 ▶); Walstrom et al. (2009 ▶). For background to the properties and applications of terpiridine complexes, see: Anders & Schubert (2004 ▶); Constable (2007 ▶); Plonska et al. (2002 ▶); Winkler et al. (2003 ▶, 2006 ▶).

Experimental

Crystal data

[Ru(C15H11N3)2](ClO4)2·0.5H2O

M = 775.51

Monoclinic,

a = 8.7676 (2) Å

b = 8.8221 (9) Å

c = 39.118 (4) Å

β = 93.582 (5)°

V = 3019.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 100 K

0.15 × 0.12 × 0.03 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.801, T max = 1.000

16537 measured reflections

6158 independent reflections

5858 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.083

S = 1.27

6158 reflections

439 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −1.17 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXD (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043917/bt6849sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043917/bt6849Isup2.hkl

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

[Ru(C15H11N3)2](ClO4)2·0.5H2O	F(000) = 1564
Mr = 775.51	Dx = 1.706 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7538 reflections
a = 8.7676 (2) Å	θ = 2.5–26.3°
b = 8.8221 (9) Å	µ = 0.76 mm−1
c = 39.118 (4) Å	T = 100 K
β = 93.582 (5)°	Plate, red
V = 3019.8 (4) Å3	0.15 × 0.12 × 0.03 mm
Z = 4

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	6158 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5858 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 10.4052 pixels mm-1	θmax = 26.4°, θmin = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = 0→11
Tmin = 0.801, Tmax = 1.000	l = 0→48
16537 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.27	w = 1/[σ2(Fo2) + (0.0111P)2 + 7.0042P] where P = (Fo2 + 2Fc2)/3
6158 reflections	(Δ/σ)max = 0.001
439 parameters	Δρmax = 0.65 e Å−3
3 restraints	Δρmin = −1.17 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ru1	0.35193 (3)	0.33315 (3)	0.127794 (6)	0.01027 (7)
N1A	0.2631 (3)	0.1164 (3)	0.12359 (7)	0.0121 (5)
N3A	0.4324 (3)	0.5408 (3)	0.11162 (7)	0.0122 (5)
C15A	0.4968 (3)	0.6520 (4)	0.13099 (8)	0.0142 (6)
H15A	0.5039	0.6399	0.1552	0.017*
C1A	0.2479 (3)	0.0135 (4)	0.14867 (8)	0.0155 (7)
H1A	0.2837	0.0386	0.1714	0.019*
C10A	0.3495 (3)	0.4333 (4)	0.05723 (8)	0.0139 (6)
C10B	0.5227 (3)	0.3134 (4)	0.19339 (8)	0.0145 (6)
C11A	0.4207 (3)	0.5607 (4)	0.07649 (8)	0.0145 (6)
C5A	0.2170 (3)	0.0758 (4)	0.09058 (8)	0.0142 (6)
C12A	0.4743 (4)	0.6915 (4)	0.06155 (9)	0.0179 (7)
H12A	0.4635	0.7042	0.0374	0.022*
C2A	0.1819 (4)	−0.1275 (4)	0.14247 (9)	0.0181 (7)
H2A	0.1724	−0.1975	0.1607	0.022*
C15B	0.6578 (3)	0.1840 (4)	0.11219 (8)	0.0156 (7)
H15B	0.6228	0.1879	0.0887	0.019*
C4A	0.1491 (4)	−0.0635 (4)	0.08320 (9)	0.0174 (7)
H4A	0.1162	−0.0888	0.0603	0.021*
C12B	0.7609 (4)	0.1731 (4)	0.17951 (9)	0.0199 (7)
H12B	0.7949	0.1700	0.2030	0.024*
C8A	0.2508 (4)	0.2943 (4)	0.00816 (8)	0.0213 (7)
H8A	0.2296	0.2866	−0.0159	0.026*
C9A	0.3187 (4)	0.4247 (4)	0.02177 (8)	0.0184 (7)
H9A	0.3437	0.5064	0.0073	0.022*
C14A	0.5534 (4)	0.7834 (4)	0.11718 (9)	0.0189 (7)
H14A	0.5985	0.8594	0.1317	0.023*
C3A	0.1300 (4)	−0.1650 (4)	0.10941 (9)	0.0211 (7)
H3A	0.0816	−0.2599	0.1048	0.025*
C13A	0.5437 (4)	0.8035 (4)	0.08197 (9)	0.0205 (7)
H13A	0.5838	0.8921	0.0720	0.025*
C4B	0.0091 (4)	0.5255 (4)	0.18713 (9)	0.0193 (7)
H4B	0.0076	0.5521	0.2106	0.023*
C7B	0.3040 (4)	0.4475 (4)	0.23114 (8)	0.0196 (7)
H7B	0.2281	0.4937	0.2440	0.024*
N2B	0.3874 (3)	0.3573 (3)	0.17813 (6)	0.0124 (5)
C6B	0.2779 (3)	0.4223 (4)	0.19610 (8)	0.0143 (6)
C14B	0.7970 (4)	0.1152 (4)	0.12103 (9)	0.0184 (7)
H14B	0.8565	0.0731	0.1039	0.022*
C1B	0.0186 (4)	0.4455 (4)	0.11975 (9)	0.0163 (7)
H1B	0.0203	0.4168	0.0964	0.020*
C13B	0.8476 (4)	0.1089 (4)	0.15514 (9)	0.0216 (7)
H13B	0.9417	0.0606	0.1618	0.026*
C5B	0.1388 (4)	0.4593 (4)	0.17462 (8)	0.0149 (7)
C2B	−0.1131 (4)	0.5101 (4)	0.13105 (9)	0.0208 (7)
H2B	−0.1997	0.5253	0.1156	0.025*
C3B	−0.1173 (4)	0.5522 (4)	0.16509 (9)	0.0223 (8)
H3B	−0.2059	0.5988	0.1732	0.027*
C8B	0.4433 (4)	0.4036 (4)	0.24683 (9)	0.0215 (7)
H8B	0.4625	0.4199	0.2707	0.026*
C9B	0.5547 (4)	0.3367 (4)	0.22841 (8)	0.0192 (7)
H9B	0.6501	0.3074	0.2393	0.023*
N1B	0.1441 (3)	0.4219 (3)	0.14059 (7)	0.0127 (5)
N2A	0.3132 (3)	0.3157 (3)	0.07744 (6)	0.0126 (5)
C6A	0.2464 (3)	0.1891 (4)	0.06429 (8)	0.0142 (6)
N3B	0.5705 (3)	0.2454 (3)	0.13564 (6)	0.0123 (5)
C7A	0.2136 (4)	0.1753 (4)	0.02910 (8)	0.0198 (7)
H7A	0.1668	0.0862	0.0197	0.024*
C11B	0.6234 (3)	0.2424 (4)	0.16936 (8)	0.0146 (7)
Cl1A	0.78661 (9)	0.20109 (9)	0.02625 (2)	0.01935 (18)
O2A	0.8387 (3)	0.2126 (3)	−0.00779 (6)	0.0306 (6)
O4A	0.6256 (3)	0.2268 (4)	0.02484 (7)	0.0426 (8)
O3A	0.8209 (4)	0.0534 (3)	0.03981 (7)	0.0383 (7)
O1A	0.8611 (4)	0.3124 (3)	0.04797 (7)	0.0407 (7)
Cl1B	0.52415 (9)	0.83287 (10)	0.22156 (2)	0.02087 (18)
O2B	0.5394 (3)	0.7741 (3)	0.25576 (7)	0.0369 (7)
O1B	0.3911 (3)	0.7690 (3)	0.20366 (6)	0.0279 (6)
O3B	0.5070 (3)	0.9946 (3)	0.22300 (7)	0.0297 (6)
O4B	0.6574 (3)	0.7965 (4)	0.20354 (7)	0.0433 (8)
O5	0.9985 (6)	0.6020 (6)	0.05038 (12)	0.0266 (11)	0.50
H5A	1.044 (8)	0.639 (8)	0.0339 (13)	0.040*	0.50
H5B	0.950 (8)	0.523 (6)	0.0438 (18)	0.040*	0.50

	U11	U22	U33	U12	U13	U23
Ru1	0.00989 (12)	0.00929 (12)	0.01172 (13)	−0.00013 (10)	0.00132 (9)	−0.00072 (10)
N1A	0.0079 (12)	0.0103 (13)	0.0179 (13)	0.0022 (10)	0.0002 (10)	−0.0004 (11)
N3A	0.0100 (12)	0.0096 (13)	0.0173 (13)	0.0017 (10)	0.0025 (10)	−0.0008 (11)
C15A	0.0119 (14)	0.0129 (16)	0.0179 (16)	0.0005 (12)	0.0008 (12)	−0.0028 (13)
C1A	0.0130 (15)	0.0161 (17)	0.0171 (16)	0.0008 (13)	0.0000 (12)	0.0015 (13)
C10A	0.0114 (15)	0.0123 (16)	0.0181 (16)	0.0039 (12)	0.0010 (12)	0.0001 (13)
C10B	0.0158 (15)	0.0109 (16)	0.0168 (16)	−0.0039 (12)	0.0002 (12)	0.0007 (13)
C11A	0.0123 (15)	0.0145 (16)	0.0171 (16)	0.0030 (13)	0.0031 (12)	−0.0005 (13)
C5A	0.0101 (15)	0.0129 (16)	0.0194 (16)	0.0024 (12)	0.0003 (12)	−0.0015 (13)
C12A	0.0190 (16)	0.0153 (17)	0.0198 (17)	−0.0005 (13)	0.0031 (13)	0.0031 (14)
C2A	0.0150 (16)	0.0119 (16)	0.0273 (18)	0.0037 (13)	0.0013 (13)	0.0053 (14)
C15B	0.0171 (16)	0.0126 (16)	0.0175 (16)	−0.0028 (13)	0.0047 (12)	−0.0005 (13)
C4A	0.0153 (16)	0.0145 (17)	0.0221 (17)	0.0000 (13)	−0.0012 (13)	−0.0031 (14)
C12B	0.0168 (16)	0.0195 (17)	0.0228 (17)	−0.0005 (14)	−0.0030 (13)	0.0026 (15)
C8A	0.0236 (18)	0.028 (2)	0.0122 (16)	−0.0017 (15)	0.0000 (13)	−0.0018 (14)
C9A	0.0204 (17)	0.0187 (18)	0.0162 (16)	0.0000 (14)	0.0026 (13)	0.0009 (14)
C14A	0.0165 (16)	0.0143 (16)	0.0260 (18)	−0.0020 (13)	0.0018 (13)	−0.0038 (14)
C3A	0.0157 (16)	0.0118 (16)	0.036 (2)	−0.0042 (14)	0.0000 (14)	−0.0010 (15)
C13A	0.0193 (17)	0.0129 (17)	0.0297 (19)	−0.0023 (13)	0.0047 (14)	0.0044 (14)
C4B	0.0207 (17)	0.0141 (17)	0.0240 (18)	0.0010 (14)	0.0093 (14)	0.0003 (14)
C7B	0.0258 (18)	0.0160 (17)	0.0178 (17)	−0.0032 (14)	0.0088 (13)	−0.0030 (14)
N2B	0.0133 (13)	0.0081 (13)	0.0161 (13)	−0.0015 (10)	0.0028 (10)	−0.0007 (10)
C6B	0.0149 (15)	0.0089 (15)	0.0195 (16)	−0.0024 (12)	0.0044 (12)	−0.0017 (13)
C14B	0.0152 (16)	0.0146 (16)	0.0262 (18)	0.0000 (13)	0.0073 (13)	−0.0003 (14)
C1B	0.0159 (16)	0.0100 (16)	0.0228 (17)	−0.0028 (13)	0.0005 (13)	0.0017 (13)
C13B	0.0147 (16)	0.0184 (18)	0.032 (2)	0.0010 (14)	0.0013 (14)	0.0041 (15)
C5B	0.0184 (16)	0.0076 (15)	0.0194 (16)	−0.0023 (12)	0.0065 (13)	0.0006 (13)
C2B	0.0134 (16)	0.0159 (17)	0.033 (2)	0.0005 (13)	0.0019 (14)	0.0046 (15)
C3B	0.0167 (17)	0.0157 (17)	0.036 (2)	0.0030 (14)	0.0111 (14)	0.0021 (15)
C8B	0.0292 (19)	0.0219 (19)	0.0134 (16)	−0.0064 (15)	0.0008 (13)	−0.0018 (14)
C9B	0.0212 (17)	0.0187 (17)	0.0171 (16)	−0.0012 (14)	−0.0049 (13)	0.0000 (14)
N1B	0.0122 (13)	0.0083 (13)	0.0179 (14)	−0.0028 (10)	0.0030 (10)	−0.0004 (11)
N2A	0.0111 (12)	0.0111 (13)	0.0155 (13)	0.0013 (10)	0.0012 (10)	0.0000 (11)
C6A	0.0116 (14)	0.0127 (16)	0.0185 (16)	0.0030 (12)	0.0017 (12)	−0.0027 (13)
N3B	0.0111 (12)	0.0101 (13)	0.0155 (13)	−0.0026 (10)	0.0000 (10)	0.0010 (11)
C7A	0.0198 (16)	0.0204 (18)	0.0190 (17)	−0.0021 (15)	−0.0010 (13)	−0.0044 (14)
C11B	0.0144 (15)	0.0120 (16)	0.0175 (16)	−0.0049 (13)	0.0008 (12)	0.0004 (13)
Cl1A	0.0207 (4)	0.0201 (4)	0.0172 (4)	0.0005 (3)	0.0013 (3)	−0.0022 (3)
O2A	0.0369 (15)	0.0372 (16)	0.0184 (13)	0.0012 (13)	0.0073 (11)	−0.0027 (12)
O4A	0.0226 (14)	0.072 (2)	0.0337 (16)	0.0097 (15)	0.0027 (12)	0.0139 (16)
O3A	0.062 (2)	0.0264 (15)	0.0263 (15)	0.0128 (14)	−0.0007 (13)	0.0011 (12)
O1A	0.0560 (19)	0.0395 (18)	0.0263 (15)	−0.0183 (15)	0.0012 (13)	−0.0127 (13)
Cl1B	0.0236 (4)	0.0194 (4)	0.0191 (4)	0.0054 (3)	−0.0023 (3)	−0.0056 (3)
O2B	0.0604 (19)	0.0273 (15)	0.0211 (14)	0.0101 (14)	−0.0127 (13)	0.0005 (12)
O1B	0.0301 (14)	0.0306 (15)	0.0218 (13)	−0.0036 (12)	−0.0073 (11)	−0.0022 (11)
O3B	0.0389 (16)	0.0187 (13)	0.0330 (15)	−0.0019 (12)	0.0143 (12)	−0.0010 (12)
O4B	0.0276 (15)	0.059 (2)	0.0432 (17)	0.0136 (14)	0.0025 (13)	−0.0240 (16)
O5	0.034 (3)	0.025 (3)	0.021 (3)	−0.010 (2)	−0.002 (2)	0.005 (2)

Ru1—N2A	1.984 (3)	C14A—C13A	1.386 (5)
Ru1—N2B	1.986 (3)	C14A—H14A	0.9500
Ru1—N1A	2.067 (3)	C3A—H3A	0.9500
Ru1—N3B	2.072 (3)	C13A—H13A	0.9500
Ru1—N1B	2.073 (3)	C4B—C3B	1.381 (5)
Ru1—N3A	2.076 (3)	C4B—C5B	1.394 (4)
N1A—C1A	1.350 (4)	C4B—H4B	0.9500
N1A—C5A	1.376 (4)	C7B—C8B	1.388 (5)
N3A—C15A	1.342 (4)	C7B—C6B	1.393 (4)
N3A—C11A	1.383 (4)	C7B—H7B	0.9500
C15A—C14A	1.384 (5)	N2B—C6B	1.352 (4)
C15A—H15A	0.9500	C6B—C5B	1.474 (4)
C1A—C2A	1.387 (5)	C14B—C13B	1.381 (5)
C1A—H1A	0.9500	C14B—H14B	0.9500
C10A—N2A	1.354 (4)	C1B—N1B	1.345 (4)
C10A—C9A	1.399 (4)	C1B—C2B	1.384 (5)
C10A—C11A	1.470 (4)	C1B—H1B	0.9500
C10B—N2B	1.351 (4)	C13B—H13B	0.9500
C10B—C9B	1.396 (4)	C5B—N1B	1.375 (4)
C10B—C11B	1.469 (4)	C2B—C3B	1.385 (5)
C11A—C12A	1.389 (4)	C2B—H2B	0.9500
C5A—C4A	1.388 (4)	C3B—H3B	0.9500
C5A—C6A	1.468 (4)	C8B—C9B	1.382 (5)
C12A—C13A	1.387 (5)	C8B—H8B	0.9500
C12A—H12A	0.9500	C9B—H9B	0.9500
C2A—C3A	1.384 (5)	N2A—C6A	1.349 (4)
C2A—H2A	0.9500	C6A—C7A	1.394 (4)
C15B—N3B	1.344 (4)	N3B—C11B	1.371 (4)
C15B—C14B	1.388 (4)	C7A—H7A	0.9500
C15B—H15B	0.9500	Cl1A—O4A	1.427 (3)
C4A—C3A	1.380 (5)	Cl1A—O1A	1.430 (3)
C4A—H4A	0.9500	Cl1A—O3A	1.432 (3)
C12B—C13B	1.378 (5)	Cl1A—O2A	1.438 (3)
C12B—C11B	1.387 (4)	Cl1B—O2B	1.433 (3)
C12B—H12B	0.9500	Cl1B—O3B	1.437 (3)
C8A—C7A	1.384 (5)	Cl1B—O1B	1.437 (3)
C8A—C9A	1.386 (5)	Cl1B—O4B	1.438 (3)
C8A—H8A	0.9500	O5—H5A	0.85 (2)
C9A—H9A	0.9500	O5—H5B	0.85 (2)
N2A—Ru1—N2B	178.09 (11)	C12A—C13A—H13A	120.7
N2A—Ru1—N1A	78.99 (10)	C3B—C4B—C5B	119.5 (3)
N2B—Ru1—N1A	102.30 (10)	C3B—C4B—H4B	120.2
N2A—Ru1—N3B	102.56 (10)	C5B—C4B—H4B	120.2
N2B—Ru1—N3B	78.88 (10)	C8B—C7B—C6B	118.4 (3)
N1A—Ru1—N3B	90.37 (10)	C8B—C7B—H7B	120.8
N2A—Ru1—N1B	99.82 (10)	C6B—C7B—H7B	120.8
N2B—Ru1—N1B	78.78 (10)	C6B—N2B—C10B	121.6 (3)
N1A—Ru1—N1B	92.06 (10)	C6B—N2B—Ru1	119.3 (2)
N3B—Ru1—N1B	157.54 (10)	C10B—N2B—Ru1	119.1 (2)
N2A—Ru1—N3A	78.81 (10)	N2B—C6B—C7B	120.1 (3)
N2B—Ru1—N3A	99.93 (10)	N2B—C6B—C5B	112.7 (3)
N1A—Ru1—N3A	157.73 (10)	C7B—C6B—C5B	127.2 (3)
N3B—Ru1—N3A	92.65 (10)	C13B—C14B—C15B	118.9 (3)
N1B—Ru1—N3A	93.49 (10)	C13B—C14B—H14B	120.5
C1A—N1A—C5A	118.1 (3)	C15B—C14B—H14B	120.5
C1A—N1A—Ru1	128.2 (2)	N1B—C1B—C2B	122.5 (3)
C5A—N1A—Ru1	113.7 (2)	N1B—C1B—H1B	118.7
C15A—N3A—C11A	118.1 (3)	C2B—C1B—H1B	118.7
C15A—N3A—Ru1	127.7 (2)	C12B—C13B—C14B	119.6 (3)
C11A—N3A—Ru1	114.1 (2)	C12B—C13B—H13B	120.2
N3A—C15A—C14A	122.7 (3)	C14B—C13B—H13B	120.2
N3A—C15A—H15A	118.7	N1B—C5B—C4B	121.2 (3)
C14A—C15A—H15A	118.7	N1B—C5B—C6B	114.9 (3)
N1A—C1A—C2A	122.4 (3)	C4B—C5B—C6B	123.8 (3)
N1A—C1A—H1A	118.8	C1B—C2B—C3B	119.4 (3)
C2A—C1A—H1A	118.8	C1B—C2B—H2B	120.3
N2A—C10A—C9A	120.0 (3)	C3B—C2B—H2B	120.3
N2A—C10A—C11A	113.2 (3)	C4B—C3B—C2B	119.1 (3)
C9A—C10A—C11A	126.8 (3)	C4B—C3B—H3B	120.5
N2B—C10B—C9B	120.5 (3)	C2B—C3B—H3B	120.5
N2B—C10B—C11B	112.7 (3)	C9B—C8B—C7B	121.3 (3)
C9B—C10B—C11B	126.8 (3)	C9B—C8B—H8B	119.3
N3A—C11A—C12A	121.1 (3)	C7B—C8B—H8B	119.3
N3A—C11A—C10A	114.5 (3)	C8B—C9B—C10B	118.0 (3)
C12A—C11A—C10A	124.3 (3)	C8B—C9B—H9B	121.0
N1A—C5A—C4A	121.5 (3)	C10B—C9B—H9B	121.0
N1A—C5A—C6A	115.2 (3)	C1B—N1B—C5B	118.3 (3)
C4A—C5A—C6A	123.3 (3)	C1B—N1B—Ru1	127.6 (2)
C13A—C12A—C11A	119.8 (3)	C5B—N1B—Ru1	114.1 (2)
C13A—C12A—H12A	120.1	C6A—N2A—C10A	121.6 (3)
C11A—C12A—H12A	120.1	C6A—N2A—Ru1	119.1 (2)
C3A—C2A—C1A	119.2 (3)	C10A—N2A—Ru1	119.2 (2)
C3A—C2A—H2A	120.4	N2A—C6A—C7A	120.5 (3)
C1A—C2A—H2A	120.4	N2A—C6A—C5A	112.8 (3)
N3B—C15B—C14B	122.4 (3)	C7A—C6A—C5A	126.7 (3)
N3B—C15B—H15B	118.8	C15B—N3B—C11B	118.5 (3)
C14B—C15B—H15B	118.8	C15B—N3B—Ru1	127.6 (2)
C3A—C4A—C5A	119.4 (3)	C11B—N3B—Ru1	113.8 (2)
C3A—C4A—H4A	120.3	C8A—C7A—C6A	118.5 (3)
C5A—C4A—H4A	120.3	C8A—C7A—H7A	120.8
C13B—C12B—C11B	119.4 (3)	C6A—C7A—H7A	120.8
C13B—C12B—H12B	120.3	N3B—C11B—C12B	121.3 (3)
C11B—C12B—H12B	120.3	N3B—C11B—C10B	115.3 (3)
C7A—C8A—C9A	120.9 (3)	C12B—C11B—C10B	123.4 (3)
C7A—C8A—H8A	119.5	O4A—Cl1A—O1A	109.1 (2)
C9A—C8A—H8A	119.5	O4A—Cl1A—O3A	110.07 (19)
C8A—C9A—C10A	118.5 (3)	O1A—Cl1A—O3A	109.10 (18)
C8A—C9A—H9A	120.7	O4A—Cl1A—O2A	108.88 (16)
C10A—C9A—H9A	120.7	O1A—Cl1A—O2A	109.99 (17)
C15A—C14A—C13A	119.6 (3)	O3A—Cl1A—O2A	109.65 (17)
C15A—C14A—H14A	120.2	O2B—Cl1B—O3B	109.08 (16)
C13A—C14A—H14A	120.2	O2B—Cl1B—O1B	109.78 (17)
C4A—C3A—C2A	119.4 (3)	O3B—Cl1B—O1B	108.93 (16)
C4A—C3A—H3A	120.3	O2B—Cl1B—O4B	110.22 (18)
C2A—C3A—H3A	120.3	O3B—Cl1B—O4B	109.33 (18)
C14A—C13A—C12A	118.6 (3)	O1B—Cl1B—O4B	109.47 (16)
C14A—C13A—H13A	120.7	H5A—O5—H5B	110 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2Ai	0.85 (2)	1.98 (3)	2.790 (6)	159 (7)
O5—H5B···O1A	0.85 (2)	2.03 (3)	2.824 (6)	157 (7)
C2B—H2B···Cg1ii	0.95	3.09 (1)	3.945 (4)	45 (1)
C14A—H14A···Cg2iii	0.95	3.01 (1)	3.878 (4)	43 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centoids of the N3A–C15A and N3B–C15B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2A i	0.85 (2)	1.98 (3)	2.790 (6)	159 (7)
O5—H5B⋯O1A	0.85 (2)	2.03 (3)	2.824 (6)	157 (7)
C2B—H2B⋯Cg1ii	0.95	3.09 (1)	3.945 (4)	45 (1)
C14A—H14A⋯Cg2iii	0.95	3.01 (1)	3.878 (4)	43 (1)

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