Bis(4-benzoyl-3-methyl-1-phenyl-1H-pyrazol-5-olato-κ(2)O,O')bis-(ethanol-κO)cobalt(II).

The title compound, [Co(C(17)H(13)N(2)O(2))(2)(C(2)H(5)OH)(2)], is a Co(II) complex with two 4-benzoyl-3-methyl-1-phenyl-1H-pyrazol-5-olate (BMPP) ligands and two coordinating ethanol mol-ecules. In the asymmetric unit, there are two half mol-ecules, with the Co(II) atoms located on inversion centres. The two cobalt complexes have slightly different geometries and in one, the ethyl group of the ethanol is disordered over two sets of sites [occupancy ratio 0.757 (7):0.243 (7)]. Each BMPP ligand is deprotonated with the negative charge delocalized. The hy-droxy group of each ethanol mol-ecule forms hydrogen bonds with a pyrazole N atom in an adjacent BMPP ligand. Weaker C-H⋯O and C-H⋯N inter-actions link the mol-ecules into a three-dimensional structure.

Related literature

For related structures, see: Raman et al. (2001 ▶); Yang et al. (2007 ▶). For general background and applications of acyl­pyrazolo­nes, see: Idemudia et al. (2012 ▶); Marchetti et al. (2005 ▶); Parihar et al. (2012 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

[Co(C17H13N2O2)2(C2H6O)2]

M = 705.65

Triclinic,

a = 11.0484 (3) Å

b = 11.2282 (3) Å

c = 14.8425 (4) Å

α = 89.205 (1)°

β = 87.678 (1)°

γ = 76.997 (1)°

V = 1792.56 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.53 mm−1

T = 200 K

0.49 × 0.36 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2008 ▶) T min = 0.84, T max = 0.94

32307 measured reflections

8869 independent reflections

7482 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.02

8869 reflections

471 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and SHELXLE (Hübschle et al., 2011 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032837/gg2088sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032837/gg2088Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032837/gg2088Isup3.cdx

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

[Co(C17H13N2O2)2(C2H6O)2]	Z = 2
Mr = 705.65	F(000) = 738
Triclinic, P1	Dx = 1.307 Mg m−3
Hall symbol: -P 1	Melting point: 219 K
a = 11.0484 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2282 (3) Å	Cell parameters from 108 reflections
c = 14.8425 (4) Å	θ = 3.8–31.5°
α = 89.205 (1)°	µ = 0.53 mm−1
β = 87.678 (1)°	T = 200 K
γ = 76.997 (1)°	Block, orange
V = 1792.56 (8) Å3	0.49 × 0.36 × 0.12 mm

Bruker APEXII CCD diffractometer	8869 independent reflections
Radiation source: sealed tube	7482 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.3333 pixels mm-1	θmax = 28.3°, θmin = 2.3°
φ and ω scans	h = −14→14
Absorption correction: numerical (SADABS; Bruker, 2008)	k = −14→14
Tmin = 0.84, Tmax = 0.94	l = −19→19
32307 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.9543P] where P = (Fo2 + 2Fc2)/3
8869 reflections	(Δ/σ)max < 0.001
471 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.47 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)
Co1	0	0	0.5	0.02644 (7)
Co2	1.0	0.5	0	0.03026 (8)
O11	−0.06104 (10)	0.16165 (9)	0.56233 (6)	0.0315 (2)
O12	0.11939 (10)	−0.05987 (10)	0.60361 (7)	0.0336 (2)
O13	0.14538 (12)	0.06673 (12)	0.43001 (9)	0.0466 (3)
H13A	0.1259	0.1075	0.3864	0.060 (7)*
O21	1.07029 (12)	0.34177 (11)	0.06276 (7)	0.0394 (3)
O22	0.87771 (11)	0.54948 (10)	0.11026 (7)	0.0359 (2)
O23	0.87494 (12)	0.41461 (12)	−0.06579 (8)	0.0462 (3)
H23A	0.8985	0.369	−0.1143	0.062 (7)*
N11	−0.10305 (11)	0.27443 (11)	0.69400 (8)	0.0280 (2)
N12	−0.05984 (13)	0.26925 (12)	0.78148 (8)	0.0341 (3)
N21	1.11456 (13)	0.22367 (12)	0.19080 (8)	0.0336 (3)
N22	1.07617 (14)	0.22544 (13)	0.28176 (8)	0.0375 (3)
C11	−0.03970 (13)	0.17640 (12)	0.64384 (9)	0.0252 (3)
C12	0.04931 (14)	0.10603 (13)	0.70179 (9)	0.0279 (3)
C13	0.02963 (15)	0.17038 (14)	0.78577 (9)	0.0335 (3)
C14	0.0899 (2)	0.1371 (2)	0.87390 (11)	0.0562 (6)
H14A	0.0953	0.0502	0.8866	0.084*
H14B	0.0402	0.1863	0.9221	0.084*
H14C	0.1736	0.1531	0.8708	0.084*
C15	0.13206 (13)	−0.00484 (13)	0.67443 (9)	0.0275 (3)
C21	1.05355 (15)	0.32601 (14)	0.14632 (9)	0.0315 (3)
C22	0.97286 (15)	0.39911 (14)	0.21254 (9)	0.0320 (3)
C23	0.99378 (16)	0.32862 (15)	0.29435 (10)	0.0362 (3)
C24	0.9383 (2)	0.35577 (17)	0.38780 (11)	0.0532 (5)
H24A	0.8479	0.3844	0.385	0.08*
H24B	0.9732	0.4192	0.4147	0.08*
H24C	0.9575	0.2814	0.4247	0.08*
C25	0.88599 (15)	0.50747 (14)	0.18943 (9)	0.0318 (3)
C26	0.7822 (3)	0.3650 (3)	−0.01816 (18)	0.0825 (9)
H26A	0.7871	0.2809	−0.0395	0.099*
H26B	0.7993	0.3604	0.0469	0.099*
C27	0.6610 (3)	0.4357 (5)	−0.0300 (4)	0.155 (2)
H27A	0.6598	0.5222	−0.0209	0.232*
H27B	0.6032	0.4099	0.0139	0.232*
H27C	0.6357	0.424	−0.0912	0.232*
C111	−0.19608 (13)	0.37569 (13)	0.66632 (10)	0.0286 (3)
C112	−0.25930 (15)	0.37105 (15)	0.58784 (11)	0.0371 (3)
H112	−0.2418	0.2989	0.5524	0.045*
C113	−0.34801 (17)	0.47218 (18)	0.56156 (13)	0.0481 (4)
H113	−0.39	0.4693	0.5073	0.058*
C114	−0.37636 (19)	0.57684 (18)	0.61289 (15)	0.0535 (5)
H114	−0.4389	0.6449	0.5952	0.064*
C115	−0.3129 (2)	0.58125 (18)	0.68994 (16)	0.0578 (5)
H115	−0.3311	0.6535	0.7252	0.069*
C116	−0.22273 (18)	0.48182 (16)	0.71716 (13)	0.0463 (4)
H116	−0.1793	0.4863	0.7705	0.056*
C121	0.24248 (14)	−0.06123 (14)	0.72766 (9)	0.0309 (3)
C122	0.2658 (2)	−0.18464 (17)	0.74798 (15)	0.0533 (5)
H122	0.2096	−0.2321	0.7307	0.064*
C123	0.3715 (2)	−0.2392 (2)	0.79362 (18)	0.0699 (7)
H123	0.3862	−0.3235	0.8089	0.084*
C124	0.45441 (19)	−0.1725 (2)	0.81670 (14)	0.0581 (5)
H124	0.5263	−0.2104	0.8481	0.07*
C125	0.43434 (17)	−0.0511 (2)	0.79472 (13)	0.0521 (5)
H125	0.4936	−0.0055	0.8094	0.063*
C126	0.32726 (17)	0.00593 (17)	0.75092 (12)	0.0428 (4)
H12A	0.3125	0.0907	0.737	0.051*
C211	1.19389 (14)	0.11779 (14)	0.15297 (10)	0.0318 (3)
C212	1.26245 (15)	0.12585 (17)	0.07298 (10)	0.0382 (3)
H212	1.2579	0.2026	0.044	0.046*
C213	1.33730 (16)	0.02042 (19)	0.03630 (12)	0.0463 (4)
H213	1.3826	0.0252	−0.0189	0.056*
C214	1.34711 (18)	−0.09108 (19)	0.07852 (14)	0.0516 (5)
H214	1.3995	−0.1624	0.053	0.062*
C215	1.28032 (19)	−0.09846 (17)	0.15823 (15)	0.0514 (5)
H215	1.2875	−0.1751	0.1879	0.062*
C216	1.20287 (17)	0.00521 (16)	0.19519 (12)	0.0418 (4)
H216	1.1559	−0.0008	0.2494	0.05*
C221	0.79264 (16)	0.57662 (15)	0.25689 (10)	0.0375 (3)
C222	0.66813 (19)	0.5958 (2)	0.23946 (14)	0.0560 (5)
H222	0.6429	0.5648	0.1858	0.067*
C223	0.5791 (2)	0.6608 (3)	0.30081 (18)	0.0757 (8)
H223	0.4931	0.6719	0.2901	0.091*
C224	0.6170 (3)	0.7090 (2)	0.37703 (16)	0.0757 (8)
H224	0.5565	0.7535	0.4187	0.091*
C225	0.7401 (3)	0.69350 (19)	0.39334 (14)	0.0635 (6)
H225	0.765	0.7285	0.4455	0.076*
C226	0.8290 (2)	0.62677 (16)	0.33398 (11)	0.0459 (4)
H226	0.9147	0.6151	0.3458	0.055*
C16A	0.2742 (3)	−0.0041 (4)	0.4279 (2)	0.0533 (9)	0.757 (7)
H16A	0.2836	−0.0705	0.3832	0.064*	0.757 (7)
H16B	0.2927	−0.0424	0.4878	0.064*	0.757 (7)
C17A	0.3656 (3)	0.0719 (3)	0.4045 (2)	0.0640 (10)	0.757 (7)
H17A	0.45	0.0206	0.4048	0.096*	0.757 (7)
H17B	0.3573	0.1374	0.4488	0.096*	0.757 (7)
H17C	0.3496	0.1078	0.3443	0.096*	0.757 (7)
C16B	0.2583 (12)	0.0716 (13)	0.4401 (8)	0.070 (4)	0.243 (7)
H16C	0.2663	0.1027	0.5012	0.084*	0.243 (7)
H16D	0.2814	0.1302	0.3958	0.084*	0.243 (7)
C17B	0.3450 (12)	−0.0480 (17)	0.4284 (10)	0.106 (6)	0.243 (7)
H17D	0.3669	−0.062	0.3642	0.159*	0.243 (7)
H17E	0.3053	−0.1125	0.4519	0.159*	0.243 (7)
H17F	0.4204	−0.0493	0.4614	0.159*	0.243 (7)

	U11	U22	U33	U12	U13	U23
Co1	0.03579 (15)	0.02519 (13)	0.01517 (12)	0.00070 (10)	−0.00458 (10)	−0.00412 (9)
Co2	0.04097 (16)	0.03298 (15)	0.01484 (12)	−0.00448 (12)	0.00239 (10)	−0.00391 (10)
O11	0.0441 (6)	0.0282 (5)	0.0180 (4)	0.0022 (4)	−0.0068 (4)	−0.0049 (4)
O12	0.0445 (6)	0.0306 (5)	0.0216 (5)	0.0021 (4)	−0.0091 (4)	−0.0060 (4)
O13	0.0443 (7)	0.0425 (7)	0.0467 (7)	0.0012 (5)	0.0090 (5)	0.0110 (6)
O21	0.0552 (7)	0.0384 (6)	0.0188 (5)	0.0007 (5)	0.0073 (4)	−0.0016 (4)
O22	0.0456 (6)	0.0379 (6)	0.0209 (5)	−0.0031 (5)	0.0045 (4)	−0.0029 (4)
O23	0.0487 (7)	0.0593 (8)	0.0324 (6)	−0.0162 (6)	0.0078 (5)	−0.0235 (5)
N11	0.0322 (6)	0.0298 (6)	0.0199 (5)	−0.0019 (5)	−0.0034 (4)	−0.0068 (4)
N12	0.0400 (7)	0.0393 (7)	0.0200 (5)	−0.0013 (6)	−0.0062 (5)	−0.0098 (5)
N21	0.0415 (7)	0.0373 (7)	0.0195 (5)	−0.0049 (6)	0.0052 (5)	−0.0018 (5)
N22	0.0508 (8)	0.0387 (7)	0.0205 (6)	−0.0065 (6)	0.0079 (5)	−0.0001 (5)
C11	0.0298 (7)	0.0255 (6)	0.0196 (6)	−0.0045 (5)	−0.0013 (5)	−0.0041 (5)
C12	0.0329 (7)	0.0309 (7)	0.0186 (6)	−0.0038 (6)	−0.0047 (5)	−0.0045 (5)
C13	0.0380 (8)	0.0381 (8)	0.0218 (6)	−0.0018 (6)	−0.0063 (6)	−0.0079 (6)
C14	0.0680 (13)	0.0625 (12)	0.0253 (8)	0.0159 (10)	−0.0182 (8)	−0.0149 (8)
C15	0.0324 (7)	0.0293 (7)	0.0199 (6)	−0.0046 (5)	−0.0042 (5)	−0.0005 (5)
C21	0.0389 (8)	0.0337 (7)	0.0217 (6)	−0.0081 (6)	0.0035 (5)	−0.0028 (5)
C22	0.0426 (8)	0.0335 (7)	0.0200 (6)	−0.0094 (6)	0.0062 (6)	−0.0035 (5)
C23	0.0493 (9)	0.0364 (8)	0.0220 (7)	−0.0093 (7)	0.0072 (6)	−0.0013 (6)
C24	0.0847 (15)	0.0415 (9)	0.0252 (8)	−0.0007 (9)	0.0183 (8)	0.0016 (7)
C25	0.0412 (8)	0.0339 (7)	0.0211 (6)	−0.0108 (6)	0.0052 (6)	−0.0051 (5)
C26	0.0781 (17)	0.118 (2)	0.0662 (15)	−0.0562 (17)	0.0244 (13)	−0.0505 (15)
C27	0.066 (2)	0.212 (6)	0.173 (5)	−0.009 (3)	0.028 (3)	−0.017 (4)
C111	0.0271 (7)	0.0295 (7)	0.0274 (7)	−0.0031 (5)	0.0015 (5)	−0.0030 (5)
C112	0.0369 (8)	0.0387 (8)	0.0316 (7)	0.0007 (7)	−0.0040 (6)	−0.0059 (6)
C113	0.0428 (10)	0.0523 (11)	0.0417 (9)	0.0066 (8)	−0.0103 (7)	−0.0007 (8)
C114	0.0479 (11)	0.0429 (10)	0.0596 (12)	0.0119 (8)	−0.0060 (9)	0.0010 (8)
C115	0.0609 (13)	0.0366 (9)	0.0669 (13)	0.0100 (9)	−0.0095 (10)	−0.0157 (9)
C116	0.0484 (10)	0.0384 (9)	0.0476 (10)	0.0022 (7)	−0.0113 (8)	−0.0150 (7)
C121	0.0332 (7)	0.0337 (7)	0.0232 (6)	−0.0008 (6)	−0.0048 (5)	−0.0050 (5)
C122	0.0572 (12)	0.0383 (9)	0.0645 (12)	−0.0062 (8)	−0.0304 (10)	0.0048 (8)
C123	0.0739 (15)	0.0438 (11)	0.0865 (17)	0.0045 (10)	−0.0421 (13)	0.0066 (11)
C124	0.0432 (10)	0.0688 (14)	0.0531 (11)	0.0107 (9)	−0.0203 (9)	−0.0118 (10)
C125	0.0369 (9)	0.0748 (14)	0.0462 (10)	−0.0138 (9)	−0.0103 (8)	−0.0100 (9)
C126	0.0444 (9)	0.0461 (10)	0.0392 (9)	−0.0117 (8)	−0.0092 (7)	−0.0016 (7)
C211	0.0302 (7)	0.0381 (8)	0.0268 (7)	−0.0072 (6)	0.0002 (5)	−0.0065 (6)
C212	0.0333 (8)	0.0508 (10)	0.0278 (7)	−0.0039 (7)	−0.0001 (6)	−0.0014 (6)
C213	0.0337 (8)	0.0670 (12)	0.0339 (8)	−0.0023 (8)	0.0031 (6)	−0.0119 (8)
C214	0.0435 (10)	0.0516 (11)	0.0573 (11)	−0.0056 (8)	0.0050 (8)	−0.0246 (9)
C215	0.0536 (11)	0.0357 (9)	0.0656 (12)	−0.0125 (8)	0.0071 (9)	−0.0110 (8)
C216	0.0468 (10)	0.0374 (9)	0.0424 (9)	−0.0138 (7)	0.0093 (7)	−0.0062 (7)
C221	0.0493 (9)	0.0329 (8)	0.0263 (7)	−0.0035 (7)	0.0128 (6)	0.0001 (6)
C222	0.0509 (11)	0.0668 (13)	0.0429 (10)	0.0005 (10)	0.0082 (8)	0.0024 (9)
C223	0.0549 (13)	0.0874 (18)	0.0668 (15)	0.0166 (12)	0.0210 (11)	0.0144 (13)
C224	0.095 (2)	0.0621 (14)	0.0505 (13)	0.0167 (13)	0.0379 (13)	0.0018 (10)
C225	0.0972 (18)	0.0469 (11)	0.0376 (10)	−0.0019 (11)	0.0259 (11)	−0.0102 (8)
C226	0.0682 (12)	0.0375 (9)	0.0301 (8)	−0.0107 (8)	0.0154 (8)	−0.0065 (6)
C16A	0.0383 (16)	0.055 (2)	0.0609 (17)	0.0003 (14)	0.0033 (12)	0.0128 (14)
C17A	0.0478 (17)	0.072 (2)	0.073 (2)	−0.0154 (14)	0.0098 (14)	−0.0167 (16)
C16B	0.083 (8)	0.059 (7)	0.083 (7)	−0.043 (6)	−0.025 (6)	0.007 (6)
C17B	0.047 (7)	0.152 (15)	0.098 (10)	0.022 (8)	−0.013 (6)	0.011 (9)

Co1—O11	2.0125 (10)	C112—H112	0.95
Co1—O11i	2.0125 (10)	C113—C114	1.378 (3)
Co1—O12	2.0721 (10)	C113—H113	0.95
Co1—O12i	2.0721 (10)	C114—C115	1.372 (3)
Co1—O13	2.1460 (12)	C114—H114	0.95
Co1—O13i	2.1461 (12)	C115—C116	1.387 (3)
Co2—O21	2.0047 (11)	C115—H115	0.95
Co2—O21ii	2.0047 (11)	C116—H116	0.95
Co2—O22	2.0786 (10)	C121—C122	1.382 (2)
Co2—O22ii	2.0786 (10)	C121—C126	1.384 (2)
Co2—O23	2.1245 (12)	C122—C123	1.389 (3)
Co2—O23ii	2.1245 (12)	C122—H122	0.95
O11—C11	1.2622 (16)	C123—C124	1.363 (3)
O12—C15	1.2550 (16)	C123—H123	0.95
O13—C16B	1.276 (11)	C124—C125	1.368 (3)
O13—C16A	1.465 (3)	C124—H124	0.95
O13—H13A	0.7956	C125—C126	1.394 (3)
O21—C21	1.2624 (17)	C125—H125	0.95
O22—C25	1.2593 (18)	C126—H12A	0.95
O23—C26	1.431 (3)	C211—C216	1.388 (2)
O23—H23A	0.8858	C211—C212	1.395 (2)
N11—C11	1.3746 (17)	C212—C213	1.386 (2)
N11—N12	1.3974 (16)	C212—H212	0.95
N11—C111	1.4189 (18)	C213—C214	1.376 (3)
N12—C13	1.313 (2)	C213—H213	0.95
N21—C21	1.370 (2)	C214—C215	1.380 (3)
N21—N22	1.3976 (16)	C214—H214	0.95
N21—C211	1.4165 (19)	C215—C216	1.385 (2)
N22—C23	1.313 (2)	C215—H215	0.95
C11—C12	1.4252 (19)	C216—H216	0.95
C12—C15	1.422 (2)	C221—C222	1.378 (3)
C12—C13	1.4336 (18)	C221—C226	1.394 (2)
C13—C14	1.496 (2)	C222—C223	1.397 (3)
C14—H14A	0.98	C222—H222	0.95
C14—H14B	0.98	C223—C224	1.380 (4)
C14—H14C	0.98	C223—H223	0.95
C15—C121	1.4934 (19)	C224—C225	1.363 (4)
C21—C22	1.434 (2)	C224—H224	0.95
C22—C25	1.417 (2)	C225—C226	1.385 (3)
C22—C23	1.438 (2)	C225—H225	0.95
C23—C24	1.500 (2)	C226—H226	0.95
C24—H24A	0.98	C16A—C17A	1.491 (5)
C24—H24B	0.98	C16A—H16A	0.99
C24—H24C	0.98	C16A—H16B	0.99
C25—C221	1.499 (2)	C17A—H17A	0.98
C26—C27	1.411 (5)	C17A—H17B	0.98
C26—H26A	0.99	C17A—H17C	0.98
C26—H26B	0.99	C16B—C17B	1.47 (2)
C27—H27A	0.98	C16B—H16C	0.99
C27—H27B	0.98	C16B—H16D	0.99
C27—H27C	0.98	C17B—H17D	0.98
C111—C116	1.387 (2)	C17B—H17E	0.98
C111—C112	1.390 (2)	C17B—H17F	0.98
C112—C113	1.386 (2)
O11—Co1—O11i	180.0	H27A—C27—H27B	109.5
O11—Co1—O12	90.12 (4)	C26—C27—H27C	109.5
O11i—Co1—O12	89.88 (4)	H27A—C27—H27C	109.5
O11—Co1—O12i	89.88 (4)	H27B—C27—H27C	109.5
O11i—Co1—O12i	90.12 (4)	C116—C111—C112	119.39 (15)
O12—Co1—O12i	180.0	C116—C111—N11	119.69 (14)
O11—Co1—O13	90.93 (5)	C112—C111—N11	120.91 (13)
O11i—Co1—O13	89.07 (5)	C113—C112—C111	119.63 (15)
O12—Co1—O13	89.14 (5)	C113—C112—H112	120.2
O12i—Co1—O13	90.86 (5)	C111—C112—H112	120.2
O11—Co1—O13i	89.07 (5)	C114—C113—C112	121.06 (17)
O11i—Co1—O13i	90.93 (5)	C114—C113—H113	119.5
O12—Co1—O13i	90.86 (5)	C112—C113—H113	119.5
O12i—Co1—O13i	89.14 (5)	C115—C114—C113	119.04 (17)
O13—Co1—O13i	180.0	C115—C114—H114	120.5
O21—Co2—O21ii	180.0	C113—C114—H114	120.5
O21—Co2—O22	88.73 (4)	C114—C115—C116	121.02 (18)
O21ii—Co2—O22	91.27 (4)	C114—C115—H115	119.5
O21—Co2—O22ii	91.27 (4)	C116—C115—H115	119.5
O21ii—Co2—O22ii	88.73 (4)	C115—C116—C111	119.84 (17)
O22—Co2—O22ii	179.9980 (10)	C115—C116—H116	120.1
O21—Co2—O23	89.54 (5)	C111—C116—H116	120.1
O21ii—Co2—O23	90.46 (5)	C122—C121—C126	119.27 (15)
O22—Co2—O23	92.76 (4)	C122—C121—C15	119.56 (14)
O22ii—Co2—O23	87.24 (4)	C126—C121—C15	120.97 (14)
O21—Co2—O23ii	90.46 (5)	C121—C122—C123	120.02 (19)
O21ii—Co2—O23ii	89.54 (5)	C121—C122—H122	120.0
O22—Co2—O23ii	87.24 (4)	C123—C122—H122	120.0
O22ii—Co2—O23ii	92.76 (4)	C124—C123—C122	120.4 (2)
O23—Co2—O23ii	180.0	C124—C123—H123	119.8
C11—O11—Co1	121.85 (9)	C122—C123—H123	119.8
C15—O12—Co1	128.43 (9)	C123—C124—C125	120.19 (18)
C16B—O13—Co1	139.3 (5)	C123—C124—H124	119.9
C16A—O13—Co1	121.07 (15)	C125—C124—H124	119.9
C16B—O13—H13A	104.2	C124—C125—C126	120.19 (18)
C16A—O13—H13A	115.2	C124—C125—H125	119.9
Co1—O13—H13A	116.1	C126—C125—H125	119.9
C21—O21—Co2	122.73 (10)	C121—C126—C125	119.86 (18)
C25—O22—Co2	128.58 (10)	C121—C126—H12A	120.1
C26—O23—Co2	122.93 (12)	C125—C126—H12A	120.1
C26—O23—H23A	106.9	C216—C211—C212	119.73 (15)
Co2—O23—H23A	121.5	C216—C211—N21	119.95 (14)
C11—N11—N12	111.13 (11)	C212—C211—N21	120.32 (14)
C11—N11—C111	128.62 (11)	C213—C212—C211	119.18 (17)
N12—N11—C111	120.16 (11)	C213—C212—H212	120.4
C13—N12—N11	106.47 (11)	C211—C212—H212	120.4
C21—N21—N22	111.42 (12)	C214—C213—C212	121.13 (17)
C21—N21—C211	127.65 (12)	C214—C213—H213	119.4
N22—N21—C211	120.37 (12)	C212—C213—H213	119.4
C23—N22—N21	106.32 (12)	C213—C214—C215	119.52 (17)
O11—C11—N11	122.94 (12)	C213—C214—H214	120.2
O11—C11—C12	131.05 (13)	C215—C214—H214	120.2
N11—C11—C12	105.98 (11)	C214—C215—C216	120.40 (19)
C15—C12—C11	122.89 (12)	C214—C215—H215	119.8
C15—C12—C13	132.25 (13)	C216—C215—H215	119.8
C11—C12—C13	104.83 (12)	C215—C216—C211	120.02 (16)
N12—C13—C12	111.57 (12)	C215—C216—H216	120.0
N12—C13—C14	118.60 (13)	C211—C216—H216	120.0
C12—C13—C14	129.73 (14)	C222—C221—C226	119.56 (17)
C13—C14—H14A	109.5	C222—C221—C25	118.70 (16)
C13—C14—H14B	109.5	C226—C221—C25	121.67 (16)
H14A—C14—H14B	109.5	C221—C222—C223	119.9 (2)
C13—C14—H14C	109.5	C221—C222—H222	120.0
H14A—C14—H14C	109.5	C223—C222—H222	120.0
H14B—C14—H14C	109.5	C224—C223—C222	119.5 (2)
O12—C15—C12	122.74 (12)	C224—C223—H223	120.2
O12—C15—C121	115.73 (13)	C222—C223—H223	120.2
C12—C15—C121	121.50 (12)	C225—C224—C223	120.8 (2)
O21—C21—N21	122.37 (13)	C225—C224—H224	119.6
O21—C21—C22	131.49 (15)	C223—C224—H224	119.6
N21—C21—C22	106.11 (12)	C224—C225—C226	120.0 (2)
C25—C22—C21	122.18 (13)	C224—C225—H225	120.0
C25—C22—C23	133.13 (14)	C226—C225—H225	120.0
C21—C22—C23	104.25 (13)	C225—C226—C221	120.1 (2)
N22—C23—C22	111.88 (13)	C225—C226—H226	120.0
N22—C23—C24	117.70 (14)	C221—C226—H226	120.0
C22—C23—C24	130.42 (15)	O13—C16A—C17A	112.7 (3)
C23—C24—H24A	109.5	O13—C16A—H16A	109.1
C23—C24—H24B	109.5	C17A—C16A—H16A	109.1
H24A—C24—H24B	109.5	O13—C16A—H16B	109.1
C23—C24—H24C	109.5	C17A—C16A—H16B	109.1
H24A—C24—H24C	109.5	H16A—C16A—H16B	107.8
H24B—C24—H24C	109.5	O13—C16B—C17B	112.6 (11)
O22—C25—C22	122.65 (13)	O13—C16B—H16C	109.1
O22—C25—C221	115.15 (14)	C17B—C16B—H16C	109.1
C22—C25—C221	122.12 (13)	O13—C16B—H16D	109.1
C27—C26—O23	112.4 (3)	C17B—C16B—H16D	109.1
C27—C26—H26A	109.1	H16C—C16B—H16D	107.8
O23—C26—H26A	109.1	C16B—C17B—H17D	109.5
C27—C26—H26B	109.1	C16B—C17B—H17E	109.5
O23—C26—H26B	109.1	H17D—C17B—H17E	109.5
H26A—C26—H26B	107.9	C16B—C17B—H17F	109.5
C26—C27—H27A	109.5	H17D—C17B—H17F	109.5
C26—C27—H27B	109.5	H17E—C17B—H17F	109.5
O12—Co1—O11—C11	−14.75 (12)	N21—N22—C23—C24	−178.81 (16)
O12i—Co1—O11—C11	165.25 (12)	C25—C22—C23—N22	172.28 (17)
O13—Co1—O11—C11	−103.89 (12)	C21—C22—C23—N22	0.03 (19)
O13i—Co1—O11—C11	76.11 (12)	C25—C22—C23—C24	−8.4 (3)
O11—Co1—O12—C15	2.27 (13)	C21—C22—C23—C24	179.35 (19)
O11i—Co1—O12—C15	−177.73 (13)	Co2—O22—C25—C22	−12.6 (2)
O13—Co1—O12—C15	93.20 (13)	Co2—O22—C25—C221	170.58 (11)
O13i—Co1—O12—C15	−86.80 (13)	C21—C22—C25—O22	−3.2 (2)
O11—Co1—O13—C16B	90.8 (10)	C23—C22—C25—O22	−174.33 (17)
O11i—Co1—O13—C16B	−89.2 (10)	C21—C22—C25—C221	173.43 (15)
O12—Co1—O13—C16B	0.7 (10)	C23—C22—C25—C221	2.3 (3)
O12i—Co1—O13—C16B	−179.3 (10)	Co2—O23—C26—C27	108.5 (3)
O11—Co1—O13—C16A	131.2 (2)	C11—N11—C111—C116	−160.85 (16)
O11i—Co1—O13—C16A	−48.8 (2)	N12—N11—C111—C116	15.4 (2)
O12—Co1—O13—C16A	41.1 (2)	C11—N11—C111—C112	17.8 (2)
O12i—Co1—O13—C16A	−138.9 (2)	N12—N11—C111—C112	−165.92 (14)
O22—Co2—O21—C21	−17.43 (13)	C116—C111—C112—C113	−0.1 (3)
O22ii—Co2—O21—C21	162.58 (13)	N11—C111—C112—C113	−178.76 (16)
O23—Co2—O21—C21	−110.20 (13)	C111—C112—C113—C114	−1.2 (3)
O23ii—Co2—O21—C21	69.80 (13)	C112—C113—C114—C115	1.7 (3)
O21—Co2—O22—C25	19.90 (13)	C113—C114—C115—C116	−0.9 (4)
O21ii—Co2—O22—C25	−160.10 (13)	C114—C115—C116—C111	−0.3 (3)
O23—Co2—O22—C25	109.38 (13)	C112—C111—C116—C115	0.8 (3)
O23ii—Co2—O22—C25	−70.62 (13)	N11—C111—C116—C115	179.53 (18)
O21—Co2—O23—C26	62.54 (19)	O12—C15—C121—C122	−49.2 (2)
O21ii—Co2—O23—C26	−117.46 (19)	C12—C15—C121—C122	132.44 (18)
O22—Co2—O23—C26	−26.17 (19)	O12—C15—C121—C126	125.62 (16)
O22ii—Co2—O23—C26	153.83 (19)	C12—C15—C121—C126	−52.7 (2)
C11—N11—N12—C13	0.52 (17)	C126—C121—C122—C123	1.9 (3)
C111—N11—N12—C13	−176.35 (14)	C15—C121—C122—C123	176.9 (2)
C21—N21—N22—C23	−1.08 (18)	C121—C122—C123—C124	−1.6 (4)
C211—N21—N22—C23	−173.12 (14)	C122—C123—C124—C125	−0.3 (4)
Co1—O11—C11—N11	−164.27 (10)	C123—C124—C125—C126	1.9 (3)
Co1—O11—C11—C12	17.8 (2)	C122—C121—C126—C125	−0.3 (3)
N12—N11—C11—O11	−179.12 (13)	C15—C121—C126—C125	−175.20 (16)
C111—N11—C11—O11	−2.6 (2)	C124—C125—C126—C121	−1.6 (3)
N12—N11—C11—C12	−0.73 (16)	C21—N21—C211—C216	−150.36 (17)
C111—N11—C11—C12	175.81 (14)	N22—N21—C211—C216	20.3 (2)
O11—C11—C12—C15	−2.9 (3)	C21—N21—C211—C212	29.1 (2)
N11—C11—C12—C15	178.94 (13)	N22—N21—C211—C212	−160.23 (15)
O11—C11—C12—C13	178.84 (16)	C216—C211—C212—C213	0.9 (2)
N11—C11—C12—C13	0.64 (16)	N21—C211—C212—C213	−178.58 (15)
N11—N12—C13—C12	−0.09 (18)	C211—C212—C213—C214	−1.5 (3)
N11—N12—C13—C14	−176.89 (16)	C212—C213—C214—C215	0.7 (3)
C15—C12—C13—N12	−178.42 (16)	C213—C214—C215—C216	0.7 (3)
C11—C12—C13—N12	−0.35 (18)	C214—C215—C216—C211	−1.2 (3)
C15—C12—C13—C14	−2.1 (3)	C212—C211—C216—C215	0.4 (3)
C11—C12—C13—C14	176.00 (19)	N21—C211—C216—C215	179.93 (16)
Co1—O12—C15—C12	9.8 (2)	O22—C25—C221—C222	54.7 (2)
Co1—O12—C15—C121	−168.49 (10)	C22—C25—C221—C222	−122.18 (19)
C11—C12—C15—O12	−12.5 (2)	O22—C25—C221—C226	−122.06 (17)
C13—C12—C15—O12	165.27 (16)	C22—C25—C221—C226	61.1 (2)
C11—C12—C15—C121	165.69 (14)	C226—C221—C222—C223	−2.6 (3)
C13—C12—C15—C121	−16.5 (3)	C25—C221—C222—C223	−179.47 (19)
Co2—O21—C21—N21	−171.43 (11)	C221—C222—C223—C224	2.2 (4)
Co2—O21—C21—C22	10.5 (3)	C222—C223—C224—C225	−0.2 (4)
N22—N21—C21—O21	−177.42 (15)	C223—C224—C225—C226	−1.3 (4)
C211—N21—C21—O21	−6.1 (3)	C224—C225—C226—C221	0.8 (3)
N22—N21—C21—C22	1.09 (18)	C222—C221—C226—C225	1.2 (3)
C211—N21—C21—C22	172.42 (15)	C25—C221—C226—C225	177.89 (17)
O21—C21—C22—C25	4.3 (3)	C16B—O13—C16A—C17A	−27.7 (10)
N21—C21—C22—C25	−173.99 (14)	Co1—O13—C16A—C17A	−160.64 (19)
O21—C21—C22—C23	177.64 (17)	C16A—O13—C16B—C17B	−1.5 (7)
N21—C21—C22—C23	−0.67 (17)	Co1—O13—C16B—C17B	72.6 (14)
N21—N22—C23—C22	0.61 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13A···N22iii	0.80	2.04	2.8314 (18)	175
O23—H23A···N12iv	0.89	1.90	2.7862 (16)	177
C16A—H16B···O12	0.99	2.56	3.192 (3)	122
C24—H24C···O11v	0.98	2.46	3.361 (2)	154
C112—H112···O11	0.95	2.24	2.8478 (19)	121
C116—H116···O23vi	0.95	2.60	3.458 (2)	151
C116—H116···N12	0.95	2.50	2.827 (2)	100
C212—H212···O21	0.95	2.31	2.848 (2)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O13—H13A⋯N22i	0.80	2.04	2.8314 (18)	175
O23—H23A⋯N12ii	0.89	1.90	2.7862 (16)	177
C16A—H16B⋯O12	0.99	2.56	3.192 (3)	122
C24—H24C⋯O11iii	0.98	2.46	3.361 (2)	154
C112—H112⋯O11	0.95	2.24	2.8478 (19)	121
C116—H116⋯O23iv	0.95	2.60	3.458 (2)	151
C116—H116⋯N12	0.95	2.50	2.827 (2)	100
C212—H212⋯O21	0.95	2.31	2.848 (2)	115

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