Bis{2-[(guanidinoimino)-meth-yl]phenolato-κ(3) N,N',O}cobalt(III) chloride hemihydrate.

The title compound, [Co(C8H9N4O)2]Cl·0.5H2O, is a solvatomorph of the corresponding trihydrate. Unlike in the structure of the latter compound, there are two different cations in the asymmetric unit of the title compound. The ligand mol-ecules are deprotonated at the phenol O atom and octa-hedrally coordinate the Co(III) atoms through the azomethine N and phenolate O atoms in a mer configuration. In the crystal, the cations, chloride ions and lattice water mol-ecules are linked by N-H⋯O, N-H⋯Cl, O-H⋯Cl and O-H⋯O inter-actions, forming a two-dimensional network parallel to (10-1).

Related literature

For direct synthesis using metal powders, see: Chygorin et al. (2012 ▶). For solvatomorphism, see: Desiraju (2004 ▶); Bernstein (2005 ▶); Nangia (2006 ▶); Brittain (2012 ▶). For the structure of the trihydrate solvatomorph of the title compound, see: Chumakov et al. (2006 ▶). For the structures of two different solvated crystalline forms of a related Schiff base ligand, see: Gutierrez et al. (2011 ▶).

Experimental

Crystal data

[Co(C8H9N4O)2]Cl·0.5H2O

M = 457.77

Triclinic,

a = 9.9043 (2) Å

b = 10.2078 (2) Å

c = 18.5358 (4) Å

α = 100.773 (2)°

β = 92.019 (2)°

γ = 91.458 (2)°

V = 1838.84 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.11 mm−1

T = 100 K

0.39 × 0.31 × 0.17 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2011 ▶), derived from an expression by Clark & Reid (1995 ▶)] T min = 0.720, T max = 0.864

84837 measured reflections

23430 independent reflections

19519 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.06

23430 reflections

522 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.07 e Å−3

Δρmin = −0.80 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004534/wm2724sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004534/wm2724Isup2.hkl

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

[Co(C8H9N4O)2]Cl·0.5H2O	Z = 4
Mr = 457.77	F(000) = 940
Triclinic, P1	Dx = 1.654 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9043 (2) Å	Cell parameters from 29670 reflections
b = 10.2078 (2) Å	θ = 2.8–40.7°
c = 18.5358 (4) Å	µ = 1.11 mm−1
α = 100.773 (2)°	T = 100 K
β = 92.019 (2)°	Block, dark red
γ = 91.458 (2)°	0.39 × 0.31 × 0.17 mm
V = 1838.84 (7) Å3

Oxford Diffraction Xcalibur diffractometer	23430 independent reflections
Graphite monochromator	19519 reflections with I > 2σ(I)
Detector resolution: 16.0009 pixels mm-1	Rint = 0.035
ω scans	θmax = 40.5°, θmin = 2.9°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011), derived from an expression by Clark & Reid (1995)]	h = −18→18
Tmin = 0.720, Tmax = 0.864	k = −18→18
84837 measured reflections	l = −33→33

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.4736P] where P = (Fo2 + 2Fc2)/3
23430 reflections	(Δ/σ)max = 0.003
522 parameters	Δρmax = 1.07 e Å−3
2 restraints	Δρmin = −0.80 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.Water molecule hydrogen atoms were refined with geometries restrained to ideal values.

	x	y	z	Uiso*/Ueq
Co1	0.827167 (13)	0.083852 (13)	0.376939 (7)	0.01187 (3)
Co2	0.611810 (13)	0.650408 (13)	0.893594 (7)	0.01106 (3)
Cl1	1.24863 (3)	−0.03691 (3)	0.287310 (15)	0.01975 (5)
Cl2	0.19760 (3)	0.96175 (3)	0.937412 (15)	0.02252 (5)
C11	0.61323 (10)	0.21108 (10)	0.46047 (5)	0.01394 (14)
O11	0.68370 (9)	0.20168 (8)	0.40119 (4)	0.01830 (14)
C12	0.62893 (10)	0.13118 (10)	0.51533 (5)	0.01361 (14)
C121	0.71910 (10)	0.02208 (10)	0.50915 (5)	0.01423 (14)
H121	0.7169	−0.0333	0.545	0.017*
N122	0.80287 (9)	−0.00421 (8)	0.45719 (5)	0.01313 (12)
N123	0.88511 (9)	−0.11340 (9)	0.45539 (5)	0.01570 (14)
H123	0.8781	−0.1706	0.4853	0.019*
C124	0.97792 (10)	−0.12184 (10)	0.40195 (6)	0.01488 (15)
N125	0.96716 (9)	−0.03880 (9)	0.35708 (5)	0.01636 (14)
H125	1.0209	−0.0395	0.3202	0.02*
N126	1.06788 (10)	−0.21989 (10)	0.39836 (6)	0.01985 (16)
H12A	1.1262	−0.2317	0.3632	0.024*
H12B	1.0682	−0.272	0.4312	0.024*
C13	0.55435 (11)	0.15794 (11)	0.57983 (6)	0.01724 (16)
H13	0.5662	0.1041	0.6161	0.021*
C14	0.46482 (11)	0.26027 (11)	0.59135 (6)	0.01894 (17)
H14	0.4189	0.2803	0.636	0.023*
C15	0.44326 (11)	0.33395 (11)	0.53561 (6)	0.01864 (17)
H15	0.3791	0.4023	0.542	0.022*
C16	0.51319 (11)	0.30936 (11)	0.47170 (6)	0.01784 (16)
H16	0.494	0.3593	0.4343	0.021*
C21	1.03067 (11)	0.29884 (10)	0.41005 (6)	0.01690 (16)
O21	0.95157 (9)	0.21235 (8)	0.43595 (4)	0.01865 (14)
C22	1.04017 (10)	0.30740 (10)	0.33508 (6)	0.01608 (15)
C221	0.95235 (11)	0.23312 (10)	0.27791 (6)	0.01705 (16)
H221	0.9631	0.2461	0.229	0.02*
N222	0.85960 (9)	0.14963 (9)	0.28963 (5)	0.01468 (13)
N223	0.77566 (11)	0.08933 (10)	0.23131 (5)	0.02135 (18)
H223	0.774	0.1141	0.1883	0.026*
C224	0.69561 (11)	−0.01190 (11)	0.24619 (6)	0.01745 (16)
N225	0.70323 (9)	−0.03298 (9)	0.31335 (5)	0.01625 (14)
H225	0.6551	−0.096	0.3281	0.02*
N226	0.61571 (12)	−0.07642 (12)	0.19052 (6)	0.0265 (2)
H22A	0.5602	−0.1413	0.1974	0.032*
H22B	0.6186	−0.054	0.147	0.032*
C23	1.13407 (11)	0.39789 (11)	0.31360 (8)	0.02135 (19)
H23	1.141	0.4005	0.2629	0.026*
C24	1.21588 (12)	0.48250 (13)	0.36462 (9)	0.0280 (3)
H24	1.2803	0.5415	0.3496	0.034*
C25	1.20178 (15)	0.47938 (13)	0.43866 (9)	0.0309 (3)
H25	1.2545	0.5398	0.4746	0.037*
C26	1.11214 (14)	0.38969 (12)	0.46114 (8)	0.0259 (2)
H26	1.1055	0.3895	0.5121	0.031*
C31	0.81815 (10)	0.45597 (10)	0.88106 (6)	0.01493 (15)
O31	0.74001 (8)	0.52997 (8)	0.84714 (4)	0.01635 (12)
C32	0.81293 (10)	0.44656 (10)	0.95638 (6)	0.01497 (15)
C321	0.72252 (10)	0.52156 (10)	1.00603 (5)	0.01487 (15)
H321	0.7267	0.5114	1.056	0.018*
N322	0.63581 (8)	0.60210 (8)	0.98648 (4)	0.01268 (12)
N323	0.55486 (9)	0.67200 (9)	1.03967 (5)	0.01466 (13)
H323	0.5584	0.6633	1.086	0.018*
C324	0.46931 (10)	0.75565 (10)	1.01209 (5)	0.01389 (14)
N325	0.47942 (9)	0.76188 (9)	0.94286 (5)	0.01487 (13)
H325	0.4291	0.8135	0.9207	0.018*
N326	0.38727 (10)	0.82889 (10)	1.05904 (5)	0.01765 (15)
H32A	0.3345	0.8869	1.0436	0.021*
H32B	0.3864	0.8187	1.1051	0.021*
C33	0.89567 (11)	0.35678 (11)	0.98563 (7)	0.01903 (17)
H33	0.8917	0.352	1.0362	0.023*
C34	0.98220 (11)	0.27588 (11)	0.94183 (7)	0.02107 (19)
H34	1.0362	0.2146	0.9617	0.025*
C35	0.98897 (11)	0.28567 (11)	0.86789 (7)	0.02109 (19)
H35	1.0486	0.2307	0.8375	0.025*
C36	0.91026 (11)	0.37418 (12)	0.83803 (7)	0.02006 (18)
H36	0.9183	0.3801	0.7878	0.024*
C41	0.39361 (9)	0.49962 (9)	0.80545 (5)	0.01243 (13)
O41	0.47794 (8)	0.50957 (7)	0.86352 (4)	0.01390 (11)
C42	0.39925 (10)	0.58283 (9)	0.75193 (5)	0.01252 (13)
C421	0.50038 (10)	0.68781 (9)	0.75368 (5)	0.01374 (14)
H421	0.5002	0.7356	0.7144	0.016*
N422	0.59111 (9)	0.71972 (8)	0.80620 (4)	0.01260 (12)
N423	0.68689 (10)	0.81840 (9)	0.80302 (5)	0.01686 (15)
H423	0.6974	0.8534	0.7636	0.02*
C424	0.76384 (10)	0.85724 (10)	0.86595 (5)	0.01469 (15)
N425	0.74711 (9)	0.78781 (9)	0.91742 (5)	0.01589 (14)
H425	0.7944	0.8033	0.9594	0.019*
N426	0.85036 (11)	0.96201 (10)	0.86903 (6)	0.02079 (17)
H42A	0.9025	0.9895	0.9087	0.025*
H42B	0.8548	1.0031	0.8314	0.025*
C43	0.30388 (10)	0.56265 (10)	0.69219 (5)	0.01464 (15)
H43	0.3078	0.6194	0.6571	0.018*
C44	0.20508 (10)	0.46259 (10)	0.68353 (6)	0.01570 (15)
H44	0.141	0.4509	0.6433	0.019*
C45	0.20096 (10)	0.37876 (10)	0.73500 (5)	0.01538 (15)
H45	0.1347	0.3082	0.7291	0.018*
C46	0.29211 (10)	0.39713 (10)	0.79446 (5)	0.01503 (15)
H46	0.2864	0.3393	0.8289	0.018*
O1	0.40782 (10)	−0.26387 (9)	0.20245 (5)	0.02312 (16)
H1B	0.3487 (18)	−0.2225 (19)	0.2271 (11)	0.030 (5)*
H1A	0.390 (2)	−0.3477 (16)	0.1956 (14)	0.048 (7)*

	U11	U22	U33	U12	U13	U23
Co1	0.01376 (5)	0.01180 (5)	0.01037 (5)	−0.00082 (4)	0.00077 (4)	0.00302 (4)
Co2	0.01325 (5)	0.01103 (5)	0.00952 (5)	−0.00078 (4)	−0.00045 (4)	0.00388 (4)
Cl1	0.02057 (10)	0.02147 (11)	0.01993 (10)	0.00328 (8)	0.00516 (8)	0.00978 (8)
Cl2	0.03053 (13)	0.02318 (11)	0.01366 (9)	0.00391 (10)	−0.00127 (9)	0.00303 (8)
C11	0.0155 (4)	0.0131 (3)	0.0139 (3)	0.0000 (3)	0.0011 (3)	0.0041 (3)
O11	0.0230 (3)	0.0180 (3)	0.0166 (3)	0.0059 (3)	0.0064 (3)	0.0085 (3)
C12	0.0144 (3)	0.0135 (3)	0.0136 (3)	0.0001 (3)	0.0012 (3)	0.0042 (3)
C121	0.0166 (4)	0.0148 (4)	0.0123 (3)	0.0003 (3)	0.0011 (3)	0.0051 (3)
N122	0.0149 (3)	0.0123 (3)	0.0126 (3)	0.0010 (2)	0.0002 (2)	0.0034 (2)
N123	0.0186 (3)	0.0143 (3)	0.0153 (3)	0.0035 (3)	0.0012 (3)	0.0051 (3)
C124	0.0143 (3)	0.0146 (4)	0.0148 (4)	0.0003 (3)	−0.0014 (3)	0.0007 (3)
N125	0.0154 (3)	0.0186 (4)	0.0155 (3)	0.0019 (3)	0.0029 (3)	0.0038 (3)
N126	0.0184 (4)	0.0184 (4)	0.0220 (4)	0.0053 (3)	−0.0013 (3)	0.0017 (3)
C13	0.0178 (4)	0.0198 (4)	0.0155 (4)	0.0016 (3)	0.0035 (3)	0.0062 (3)
C14	0.0188 (4)	0.0196 (4)	0.0196 (4)	0.0021 (3)	0.0058 (3)	0.0056 (3)
C15	0.0179 (4)	0.0172 (4)	0.0214 (4)	0.0030 (3)	0.0038 (3)	0.0044 (3)
C16	0.0196 (4)	0.0164 (4)	0.0191 (4)	0.0037 (3)	0.0020 (3)	0.0067 (3)
C21	0.0181 (4)	0.0128 (3)	0.0196 (4)	−0.0012 (3)	−0.0019 (3)	0.0032 (3)
O21	0.0250 (4)	0.0165 (3)	0.0138 (3)	−0.0065 (3)	−0.0014 (3)	0.0026 (2)
C22	0.0146 (4)	0.0137 (4)	0.0204 (4)	−0.0005 (3)	0.0020 (3)	0.0044 (3)
C221	0.0211 (4)	0.0157 (4)	0.0148 (4)	−0.0020 (3)	0.0042 (3)	0.0040 (3)
N222	0.0183 (3)	0.0145 (3)	0.0112 (3)	−0.0023 (3)	0.0007 (2)	0.0027 (2)
N223	0.0319 (5)	0.0207 (4)	0.0112 (3)	−0.0099 (4)	−0.0026 (3)	0.0043 (3)
C224	0.0204 (4)	0.0161 (4)	0.0156 (4)	−0.0029 (3)	−0.0032 (3)	0.0035 (3)
N225	0.0176 (3)	0.0164 (3)	0.0155 (3)	−0.0042 (3)	−0.0014 (3)	0.0058 (3)
N226	0.0330 (5)	0.0265 (5)	0.0191 (4)	−0.0122 (4)	−0.0104 (4)	0.0055 (4)
C23	0.0164 (4)	0.0168 (4)	0.0328 (6)	−0.0004 (3)	0.0048 (4)	0.0091 (4)
C24	0.0169 (4)	0.0191 (5)	0.0503 (8)	−0.0044 (4)	−0.0043 (5)	0.0143 (5)
C25	0.0296 (6)	0.0192 (5)	0.0440 (8)	−0.0086 (4)	−0.0168 (5)	0.0111 (5)
C26	0.0319 (6)	0.0173 (4)	0.0276 (5)	−0.0068 (4)	−0.0117 (5)	0.0054 (4)
C31	0.0136 (3)	0.0142 (4)	0.0177 (4)	−0.0008 (3)	0.0002 (3)	0.0052 (3)
O31	0.0179 (3)	0.0184 (3)	0.0144 (3)	0.0044 (2)	0.0024 (2)	0.0064 (2)
C32	0.0145 (3)	0.0140 (3)	0.0172 (4)	−0.0016 (3)	−0.0024 (3)	0.0057 (3)
C321	0.0168 (4)	0.0154 (4)	0.0133 (3)	−0.0017 (3)	−0.0024 (3)	0.0058 (3)
N322	0.0145 (3)	0.0133 (3)	0.0108 (3)	−0.0009 (2)	−0.0008 (2)	0.0040 (2)
N323	0.0176 (3)	0.0172 (3)	0.0100 (3)	−0.0001 (3)	0.0005 (2)	0.0047 (2)
C324	0.0152 (3)	0.0143 (3)	0.0119 (3)	−0.0018 (3)	−0.0008 (3)	0.0022 (3)
N325	0.0183 (3)	0.0155 (3)	0.0114 (3)	0.0021 (3)	−0.0003 (2)	0.0041 (2)
N326	0.0188 (4)	0.0198 (4)	0.0140 (3)	0.0015 (3)	0.0016 (3)	0.0018 (3)
C33	0.0181 (4)	0.0173 (4)	0.0227 (4)	−0.0001 (3)	−0.0048 (3)	0.0075 (3)
C34	0.0161 (4)	0.0174 (4)	0.0308 (5)	0.0006 (3)	−0.0045 (4)	0.0082 (4)
C35	0.0158 (4)	0.0179 (4)	0.0304 (5)	0.0020 (3)	0.0018 (4)	0.0063 (4)
C36	0.0180 (4)	0.0204 (4)	0.0235 (5)	0.0039 (3)	0.0041 (3)	0.0074 (4)
C41	0.0142 (3)	0.0126 (3)	0.0109 (3)	−0.0001 (3)	−0.0002 (3)	0.0034 (3)
O41	0.0169 (3)	0.0139 (3)	0.0115 (3)	−0.0035 (2)	−0.0028 (2)	0.0053 (2)
C42	0.0146 (3)	0.0125 (3)	0.0108 (3)	0.0004 (3)	−0.0005 (3)	0.0032 (3)
C421	0.0181 (4)	0.0129 (3)	0.0109 (3)	−0.0011 (3)	−0.0005 (3)	0.0042 (3)
N422	0.0154 (3)	0.0116 (3)	0.0114 (3)	−0.0018 (2)	0.0000 (2)	0.0040 (2)
N423	0.0221 (4)	0.0159 (3)	0.0133 (3)	−0.0075 (3)	−0.0023 (3)	0.0064 (3)
C424	0.0167 (4)	0.0143 (3)	0.0134 (3)	−0.0027 (3)	−0.0009 (3)	0.0039 (3)
N425	0.0184 (3)	0.0167 (3)	0.0133 (3)	−0.0045 (3)	−0.0032 (3)	0.0060 (3)
N426	0.0239 (4)	0.0202 (4)	0.0188 (4)	−0.0101 (3)	−0.0045 (3)	0.0077 (3)
C43	0.0173 (4)	0.0151 (4)	0.0119 (3)	0.0007 (3)	−0.0017 (3)	0.0040 (3)
C44	0.0154 (4)	0.0176 (4)	0.0137 (3)	0.0007 (3)	−0.0021 (3)	0.0024 (3)
C45	0.0148 (4)	0.0169 (4)	0.0140 (4)	−0.0017 (3)	−0.0002 (3)	0.0023 (3)
C46	0.0164 (4)	0.0155 (4)	0.0137 (3)	−0.0021 (3)	−0.0005 (3)	0.0047 (3)
O1	0.0218 (4)	0.0188 (4)	0.0273 (4)	−0.0004 (3)	0.0044 (3)	−0.0001 (3)

Co1—N125	1.8914 (9)	C24—C25	1.391 (2)
Co1—N122	1.8955 (8)	C24—H24	0.95
Co1—O11	1.8967 (8)	C25—C26	1.3883 (19)
Co1—N222	1.8987 (9)	C25—H25	0.95
Co1—N225	1.9017 (9)	C26—H26	0.95
Co1—O21	1.9290 (8)	C31—O31	1.3183 (13)
Co2—N322	1.8863 (8)	C31—C36	1.4165 (15)
Co2—N422	1.8918 (8)	C31—C32	1.4199 (15)
Co2—N425	1.8945 (9)	C32—C33	1.4135 (14)
Co2—N325	1.9026 (9)	C32—C321	1.4367 (15)
Co2—O31	1.9041 (8)	C321—N322	1.2924 (13)
Co2—O41	1.9202 (7)	C321—H321	0.95
C11—O11	1.3122 (13)	N322—N323	1.3949 (12)
C11—C16	1.4208 (14)	N323—C324	1.3704 (13)
C11—C12	1.4244 (13)	N323—H323	0.88
C12—C13	1.4142 (14)	C324—N325	1.3038 (13)
C12—C121	1.4356 (14)	C324—N326	1.3468 (14)
C121—N122	1.2880 (13)	N325—H325	0.88
C121—H121	0.95	N326—H32A	0.88
N122—N123	1.3932 (12)	N326—H32B	0.88
N123—C124	1.3674 (14)	C33—C34	1.3820 (18)
N123—H123	0.88	C33—H33	0.95
C124—N125	1.2976 (14)	C34—C35	1.3965 (18)
C124—N126	1.3509 (14)	C34—H34	0.95
N125—H125	0.88	C35—C36	1.3866 (16)
N126—H12A	0.88	C35—H35	0.95
N126—H12B	0.88	C36—H36	0.95
C13—C14	1.3784 (16)	C41—O41	1.3257 (12)
C13—H13	0.95	C41—C46	1.4138 (14)
C14—C15	1.4007 (16)	C41—C42	1.4232 (13)
C14—H14	0.95	C42—C43	1.4114 (13)
C15—C16	1.3790 (16)	C42—C421	1.4432 (13)
C15—H15	0.95	C421—N422	1.2909 (13)
C16—H16	0.95	C421—H421	0.95
C21—O21	1.3318 (13)	N422—N423	1.3768 (12)
C21—C26	1.4099 (16)	N423—C424	1.3594 (13)
C21—C22	1.4148 (16)	N423—H423	0.88
C22—C23	1.4130 (15)	C424—N425	1.3030 (13)
C22—C221	1.4337 (15)	C424—N426	1.3448 (13)
C221—N222	1.2887 (13)	N425—H425	0.88
C221—H221	0.95	N426—H42A	0.88
N222—N223	1.3786 (13)	N426—H42B	0.88
N223—C224	1.3612 (14)	C43—C44	1.3796 (15)
N223—H223	0.88	C43—H43	0.95
C224—N225	1.3023 (14)	C44—C45	1.3965 (15)
C224—N226	1.3366 (14)	C44—H44	0.95
N225—H225	0.88	C45—C46	1.3817 (14)
N226—H22A	0.88	C45—H45	0.95
N226—H22B	0.88	C46—H46	0.95
C23—C24	1.3792 (19)	O1—H1B	0.831 (15)
C23—H23	0.95	O1—H1A	0.855 (16)
N125—Co1—N122	82.33 (4)	C224—N226—H22B	120
N125—Co1—O11	176.71 (4)	H22A—N226—H22B	120
N122—Co1—O11	94.41 (3)	C24—C23—C22	121.45 (12)
N125—Co1—N222	90.99 (4)	C24—C23—H23	119.3
N122—Co1—N222	172.24 (4)	C22—C23—H23	119.3
O11—Co1—N222	92.24 (4)	C23—C24—C25	118.35 (11)
N125—Co1—N225	91.40 (4)	C23—C24—H24	120.8
N122—Co1—N225	93.71 (4)	C25—C24—H24	120.8
O11—Co1—N225	88.41 (4)	C26—C25—C24	121.32 (12)
N222—Co1—N225	82.46 (4)	C26—C25—H25	119.3
N125—Co1—O21	90.54 (4)	C24—C25—H25	119.3
N122—Co1—O21	90.76 (4)	C25—C26—C21	121.52 (13)
O11—Co1—O21	89.88 (4)	C25—C26—H26	119.2
N222—Co1—O21	93.26 (4)	C21—C26—H26	119.2
N225—Co1—O21	175.32 (4)	O31—C31—C36	117.30 (10)
N322—Co2—N422	173.31 (4)	O31—C31—C32	125.34 (9)
N322—Co2—N425	91.61 (4)	C36—C31—C32	117.29 (9)
N422—Co2—N425	83.09 (4)	C31—O31—Co2	124.92 (7)
N322—Co2—N325	82.54 (4)	C33—C32—C31	120.31 (10)
N422—Co2—N325	93.51 (4)	C33—C32—C321	116.39 (9)
N425—Co2—N325	91.69 (4)	C31—C32—C321	123.26 (9)
N322—Co2—O31	94.86 (4)	N322—C321—C32	123.59 (9)
N422—Co2—O31	89.31 (3)	N322—C321—H321	118.2
N425—Co2—O31	90.92 (4)	C32—C321—H321	118.2
N325—Co2—O31	176.37 (4)	C321—N322—N323	118.73 (8)
N322—Co2—O41	91.23 (3)	C321—N322—Co2	127.74 (7)
N422—Co2—O41	94.22 (3)	N323—N322—Co2	113.34 (6)
N425—Co2—O41	176.60 (4)	C324—N323—N322	112.88 (8)
N325—Co2—O41	90.55 (4)	C324—N323—H323	123.6
O31—Co2—O41	86.96 (4)	N322—N323—H323	123.6
O11—C11—C16	117.83 (9)	N325—C324—N326	125.59 (10)
O11—C11—C12	125.45 (9)	N325—C324—N323	116.56 (9)
C16—C11—C12	116.72 (9)	N326—C324—N323	117.76 (9)
C11—O11—Co1	125.27 (7)	C324—N325—Co2	114.58 (7)
C13—C12—C11	120.15 (9)	C324—N325—H325	122.7
C13—C12—C121	116.76 (9)	Co2—N325—H325	122.7
C11—C12—C121	123.09 (9)	C324—N326—H32A	120
N122—C121—C12	123.01 (9)	C324—N326—H32B	120
N122—C121—H121	118.5	H32A—N326—H32B	120
C12—C121—H121	118.5	C34—C33—C32	121.06 (11)
C121—N122—N123	118.73 (8)	C34—C33—H33	119.5
C121—N122—Co1	128.28 (7)	C32—C33—H33	119.5
N123—N122—Co1	112.94 (6)	C33—C34—C35	118.93 (10)
C124—N123—N122	112.47 (8)	C33—C34—H34	120.5
C124—N123—H123	123.8	C35—C34—H34	120.5
N122—N123—H123	123.8	C36—C35—C34	121.18 (11)
N125—C124—N126	125.95 (10)	C36—C35—H35	119.4
N125—C124—N123	116.79 (9)	C34—C35—H35	119.4
N126—C124—N123	117.17 (10)	C35—C36—C31	121.20 (11)
C124—N125—Co1	114.90 (7)	C35—C36—H36	119.4
C124—N125—H125	122.6	C31—C36—H36	119.4
Co1—N125—H125	122.6	O41—C41—C46	118.06 (8)
C124—N126—H12A	120	O41—C41—C42	124.85 (8)
C124—N126—H12B	120	C46—C41—C42	117.07 (8)
H12A—N126—H12B	120	C41—O41—Co2	124.80 (6)
C14—C13—C12	121.56 (10)	C43—C42—C41	119.80 (9)
C14—C13—H13	119.2	C43—C42—C421	116.49 (8)
C12—C13—H13	119.2	C41—C42—C421	123.69 (8)
C13—C14—C15	118.39 (10)	N422—C421—C42	123.03 (8)
C13—C14—H14	120.8	N422—C421—H421	118.5
C15—C14—H14	120.8	C42—C421—H421	118.5
C16—C15—C14	121.43 (10)	C421—N422—N423	119.74 (8)
C16—C15—H15	119.3	C421—N422—Co2	128.41 (7)
C14—C15—H15	119.3	N423—N422—Co2	111.83 (6)
C15—C16—C11	121.47 (10)	C424—N423—N422	114.35 (8)
C15—C16—H16	119.3	C424—N423—H423	122.8
C11—C16—H16	119.3	N422—N423—H423	122.8
O21—C21—C26	117.74 (10)	N425—C424—N426	126.29 (9)
O21—C21—C22	125.39 (9)	N425—C424—N423	116.35 (9)
C26—C21—C22	116.87 (10)	N426—C424—N423	117.36 (9)
C21—O21—Co1	124.97 (7)	C424—N425—Co2	113.87 (7)
C23—C22—C21	120.36 (10)	C424—N425—H425	123.1
C23—C22—C221	116.38 (10)	Co2—N425—H425	123.1
C21—C22—C221	123.16 (9)	C424—N426—H42A	120
N222—C221—C22	123.24 (9)	C424—N426—H42B	120
N222—C221—H221	118.4	H42A—N426—H42B	120
C22—C221—H221	118.4	C44—C43—C42	121.65 (9)
C221—N222—N223	118.41 (9)	C44—C43—H43	119.2
C221—N222—Co1	128.88 (8)	C42—C43—H43	119.2
N223—N222—Co1	112.52 (6)	C43—C44—C45	118.77 (9)
C224—N223—N222	114.01 (9)	C43—C44—H44	120.6
C224—N223—H223	123	C45—C44—H44	120.6
N222—N223—H223	123	C46—C45—C44	120.81 (9)
N225—C224—N226	127.36 (10)	C46—C45—H45	119.6
N225—C224—N223	116.43 (9)	C44—C45—H45	119.6
N226—C224—N223	116.19 (10)	C45—C46—C41	121.87 (9)
C224—N225—Co1	114.34 (7)	C45—C46—H46	119.1
C224—N225—H225	122.8	C41—C46—H46	119.1
Co1—N225—H225	122.8	H1B—O1—H1A	110 (2)
C224—N226—H22A	120

D—H···A	D—H	H···A	D···A	D—H···A
N123—H123···O21i	0.88	2.29	2.8823 (12)	124
N125—H125···Cl1	0.88	2.36	3.1152 (9)	144
N126—H12B···O21i	0.88	2.44	3.0709 (13)	129
N223—H223···Cl2ii	0.88	2.34	3.0948 (10)	144
N226—H22A···O1	0.88	1.95	2.8177 (14)	167
N226—H22B···Cl2ii	0.88	2.7	3.4131 (12)	138
N323—H323···O41iii	0.88	2.17	2.8311 (11)	131
N325—H325···Cl2	0.88	2.77	3.5086 (9)	142
N326—H32A···Cl2	0.88	2.59	3.3801 (10)	149
N326—H32B···O1iv	0.88	2.14	2.9861 (14)	162
N423—H423···Cl1v	0.88	2.31	3.0960 (9)	149
N425—H425···Cl2vi	0.88	2.77	3.3659 (10)	126
N426—H42B···Cl1v	0.88	2.48	3.2573 (10)	148
O1—H1B···Cl1vii	0.83 (2)	2.28 (2)	3.0538 (10)	155 (2)
O1—H1A···O31viii	0.86 (2)	2.23 (2)	3.0227 (12)	153 (2)
O1—H1A···O41viii	0.86 (2)	2.28 (2)	2.8568 (12)	125 (2)

Table 1

Selected bond lengths (Å)

Co1—N125	1.8914 (9)
Co1—N122	1.8955 (8)
Co1—O11	1.8967 (8)
Co1—N222	1.8987 (9)
Co1—N225	1.9017 (9)
Co1—O21	1.9290 (8)
Co2—N322	1.8863 (8)
Co2—N422	1.8918 (8)
Co2—N425	1.8945 (9)
Co2—N325	1.9026 (9)
Co2—O31	1.9041 (8)
Co2—O41	1.9202 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N123—H123⋯O21i	0.88	2.29	2.8823 (12)	124
N125—H125⋯Cl1	0.88	2.36	3.1152 (9)	144
N126—H12B⋯O21i	0.88	2.44	3.0709 (13)	129
N223—H223⋯Cl2ii	0.88	2.34	3.0948 (10)	144
N226—H22A⋯O1	0.88	1.95	2.8177 (14)	167
N226—H22B⋯Cl2ii	0.88	2.7	3.4131 (12)	138
N323—H323⋯O41iii	0.88	2.17	2.8311 (11)	131
N325—H325⋯Cl2	0.88	2.77	3.5086 (9)	142
N326—H32A⋯Cl2	0.88	2.59	3.3801 (10)	149
N326—H32B⋯O1iv	0.88	2.14	2.9861 (14)	162
N423—H423⋯Cl1v	0.88	2.31	3.0960 (9)	149
N425—H425⋯Cl2vi	0.88	2.77	3.3659 (10)	126
N426—H42B⋯Cl1v	0.88	2.48	3.2573 (10)	148
O1—H1B⋯Cl1vii	0.83 (2)	2.28 (2)	3.0538 (10)	155 (2)
O1—H1A⋯O31viii	0.86 (2)	2.23 (2)	3.0227 (12)	153 (2)
O1—H1A⋯O41viii	0.86 (2)	2.28 (2)	2.8568 (12)	125 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .