Bis­[μ-2,2′-(butane-1,4-diyl)di-1H-benz­imidazole-κ²N³:N^3′]bis­[diacetatocobalt(II)] ethanol disolvate

In the title compound, [Co₂(CH₃COO)₄(C₁₈H₁₈N₄)₂]·2C₂H₅OH, the asymmetric unit consists of half each of two independent complex mol­ecules, which are located about centres of inversion, and two mol­ecules of ethanol. Each Co^II atom is four-coordinated by two N atoms from two 2,2′-(butane-1,4-diyl)-1H-benzimid­azole ligands and two O atoms from two acetate ions in a slightly distorted tetra­hedral coordination environment. In the crystal packing, the mol­ecules are linked by a complex three-dimensional network of N—H...O, O—H...O and O—H...N hydrogen-bond inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.053
• wR factor = 0.151
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.94
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.37 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.97 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C43
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C47
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C38
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C40
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C42
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C44
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      32.00 A   3 

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

bis[µ-2,2'-(butane-1,4-diyl)-1H-benzimidazole- κ²N³:N^3']bis[diacetatocobalt(II)] ethanol disolvate

Crystal data

[Co2(C2H3O2)4(C18H18N4)2]·2C2H6O	Z = 2
Mr = 1026.90	F(000) = 1076
Triclinic, P1	Dx = 1.328 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.723 (3) Å	Cell parameters from 11942 reflections
b = 14.082 (3) Å	θ = 1.4–27.4°
c = 15.462 (3) Å	µ = 0.71 mm^−1
α = 73.74 (3)°	T = 292 K
β = 88.11 (3)°	Block, purple
γ = 75.17 (3)°	0.41 × 0.37 × 0.31 mm
V = 2568.6 (11) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	10986 independent reflections
Radiation source: rotor target	6829 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 10.0 pixels mm^-1	θmax = 27.4°, θmin = 1.4°
ω scans	h = 0→16
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→18
Tmin = 0.751, Tmax = 0.800	l = −19→20
10986 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0886P)^2] where P = (Fo^2 + 2Fc^2)/3
10986 reflections	(Δ/σ)max = 0.001
613 parameters	Δρmax = 1.01 e Å^−3
1 restraint	Δρmin = −0.53 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9855 (3)	1.2987 (2)	0.6620 (2)	0.0315 (7)
C2	1.0524 (3)	1.3597 (3)	0.6694 (3)	0.0425 (9)
H2	1.0982	1.3800	0.6236	0.051*
C3	1.0483 (3)	1.3894 (3)	0.7476 (3)	0.0522 (10)
H3	1.0925	1.4303	0.7545	0.063*
C4	0.9797 (4)	1.3595 (3)	0.8165 (3)	0.0585 (11)
H4	0.9798	1.3805	0.8684	0.070*
C5	0.9117 (3)	1.2997 (3)	0.8094 (3)	0.0487 (10)
H5	0.8653	1.2804	0.8548	0.058*
C6	0.9164 (3)	1.2701 (3)	0.7308 (2)	0.0348 (7)
C7	0.8944 (2)	1.2070 (2)	0.6197 (2)	0.0287 (7)
C8	0.8471 (3)	1.1532 (2)	0.5669 (2)	0.0340 (7)
H8A	0.8926	1.1456	0.5165	0.041*
H8B	0.7758	1.1956	0.5425	0.041*
C9	0.8356 (2)	1.0480 (2)	0.6207 (2)	0.0317 (7)
H9A	0.8014	1.0533	0.6767	0.038*
H9B	0.7880	1.0264	0.5867	0.038*
C10	0.9432 (3)	0.9665 (2)	0.6423 (2)	0.0323 (7)
H10A	0.9892	0.9848	0.6804	0.039*
H10B	0.9802	0.9637	0.5869	0.039*
C11	0.9256 (3)	0.8613 (2)	0.6902 (2)	0.0334 (7)
H11A	0.9110	0.8578	0.7529	0.040*
H11B	0.8622	0.8532	0.6628	0.040*
C12	1.0209 (3)	0.7756 (2)	0.6862 (2)	0.0315 (7)
C13	1.1350 (3)	0.6551 (2)	0.6444 (2)	0.0355 (8)
C14	1.1894 (3)	0.5815 (3)	0.6025 (3)	0.0456 (9)
H14	1.1584	0.5722	0.5528	0.055*
C15	1.2913 (3)	0.5231 (3)	0.6381 (3)	0.0584 (12)
H15	1.3298	0.4741	0.6111	0.070*
C16	1.3382 (3)	0.5352 (3)	0.7132 (3)	0.0591 (12)
H16	1.4072	0.4945	0.7348	0.071*
C17	1.2850 (3)	0.6058 (3)	0.7558 (3)	0.0555 (11)
H17	1.3158	0.6136	0.8062	0.067*
C18	1.1826 (3)	0.6653 (3)	0.7200 (2)	0.0417 (8)
C19	0.5713 (3)	0.7342 (2)	0.3643 (2)	0.0332 (7)
C20	0.5548 (3)	0.7105 (3)	0.4566 (2)	0.0426 (9)
H20	0.5963	0.7267	0.4961	0.051*
C21	0.4740 (3)	0.6622 (3)	0.4861 (2)	0.0482 (9)
H21	0.4602	0.6452	0.5472	0.058*
C22	0.4120 (3)	0.6380 (3)	0.4263 (2)	0.0449 (9)
H22	0.3585	0.6045	0.4489	0.054*
C23	0.4277 (3)	0.6625 (3)	0.3345 (2)	0.0367 (8)
H23	0.3861	0.6465	0.2950	0.044*
C24	0.5094 (2)	0.7127 (2)	0.3042 (2)	0.0297 (7)
C25	0.6271 (3)	0.7865 (2)	0.2267 (2)	0.0299 (7)
C26	0.6910 (3)	0.8338 (2)	0.1530 (2)	0.0345 (7)
H26A	0.6622	0.8335	0.0958	0.041*
H26B	0.7659	0.7930	0.1609	0.041*
C27	0.6885 (3)	0.9434 (2)	0.1504 (2)	0.0316 (7)
H27A	0.7175	0.9436	0.2076	0.038*
H27B	0.7351	0.9690	0.1036	0.038*
C28	0.5750 (3)	1.0143 (2)	0.1325 (2)	0.0319 (7)
H28A	0.5290	0.9908	0.1808	0.038*
H28B	0.5446	1.0121	0.0767	0.038*
C29	0.5754 (3)	1.1244 (2)	0.1259 (2)	0.0334 (7)
H29A	0.5924	1.1287	0.1852	0.040*
H29B	0.6322	1.1429	0.0864	0.040*
C30	0.4700 (3)	1.1987 (2)	0.0912 (2)	0.0317 (7)
C31	0.3003 (3)	1.2879 (2)	0.0947 (2)	0.0335 (7)
C32	0.1976 (3)	1.3354 (3)	0.1162 (3)	0.0463 (9)
H32	0.1756	1.3232	0.1754	0.056*
C33	0.1301 (3)	1.4014 (3)	0.0459 (3)	0.0528 (10)
H33	0.0599	1.4338	0.0575	0.063*
C34	0.1637 (3)	1.4215 (3)	−0.0428 (3)	0.0507 (10)
H34	0.1160	1.4683	−0.0885	0.061*
C35	0.2657 (3)	1.3735 (3)	−0.0644 (2)	0.0389 (8)
H35	0.2875	1.3862	−0.1236	0.047*
C36	0.3342 (3)	1.3057 (2)	0.0060 (2)	0.0316 (7)
C37	1.1870 (3)	1.3700 (3)	0.4033 (2)	0.0374 (8)
C38	1.2410 (3)	1.4549 (3)	0.3638 (3)	0.0530 (10)
H38A	1.2154	1.5087	0.3921	0.080*
H38B	1.2236	1.4813	0.3002	0.080*
H38C	1.3184	1.4290	0.3737	0.080*
C39	1.1974 (3)	1.0772 (3)	0.5817 (2)	0.0347 (7)
C40	1.2499 (3)	0.9671 (3)	0.6247 (3)	0.0543 (10)
H40A	1.2258	0.9261	0.5932	0.081*
H40B	1.2302	0.9488	0.6865	0.081*
H40C	1.3275	0.9554	0.6221	0.081*
C41	0.3623 (3)	0.6243 (3)	0.0760 (3)	0.0496 (10)
C42	0.3358 (5)	0.5260 (4)	0.0793 (4)	0.100 (2)
H42A	0.3733	0.4732	0.1305	0.151*
H42B	0.3583	0.5074	0.0251	0.151*
H42C	0.2587	0.5344	0.0843	0.151*
C43	0.3082 (3)	0.9232 (3)	0.1219 (2)	0.0349 (7)
C44	0.2507 (4)	1.0341 (3)	0.1070 (3)	0.0611 (12)
H44A	0.2764	1.0743	0.0537	0.092*
H44B	0.2650	1.0557	0.1580	0.092*
H44C	0.1738	1.0432	0.0996	0.092*
C45	0.4037 (4)	1.0860 (3)	0.3990 (3)	0.0575 (11)
H45A	0.3360	1.0817	0.4287	0.069*
H45B	0.4559	1.0864	0.4432	0.069*
C46	0.4454 (4)	0.9949 (3)	0.3647 (3)	0.0618 (12)
H46A	0.4563	0.9337	0.4140	0.093*
H46B	0.5133	0.9983	0.3366	0.093*
H46C	0.3935	0.9941	0.3214	0.093*
C47	0.0869 (9)	0.8587 (9)	−0.0530 (6)	0.238 (8)
H47A	0.1281	0.8594	−0.0016	0.286*
H47B	0.0237	0.8339	−0.0317	0.286*
C48	0.0549 (7)	0.9593 (9)	−0.1157 (7)	0.220 (7)
H48A	0.0092	1.0057	−0.0866	0.329*
H48B	0.0158	0.9566	−0.1666	0.329*
H48C	0.1186	0.9826	−0.1357	0.329*
N1	0.9700 (2)	1.2577 (2)	0.59190 (17)	0.0317 (6)
N2	0.8610 (2)	1.2121 (2)	0.70190 (18)	0.0339 (6)
H2A	0.8131	1.1839	0.7314	0.041*
N3	1.0336 (2)	0.7257 (2)	0.62408 (17)	0.0318 (6)
N4	1.1081 (2)	0.7423 (2)	0.7446 (2)	0.0427 (7)
H4A	1.1158	0.7652	0.7894	0.051*
N5	0.5455 (2)	0.74613 (19)	0.21696 (17)	0.0285 (6)
N6	0.6447 (2)	0.7809 (2)	0.31326 (18)	0.0331 (6)
H6	0.6934	0.8026	0.3335	0.040*
N7	0.4414 (2)	1.2470 (2)	0.00549 (17)	0.0307 (6)
N8	0.3886 (2)	1.2211 (2)	0.14648 (18)	0.0365 (7)
H8	0.3916	1.1975	0.2043	0.044*
O1	1.1198 (2)	1.37945 (19)	0.46331 (17)	0.0461 (6)
O2	1.2082 (2)	1.2915 (2)	0.37627 (19)	0.0496 (7)
O3	1.13210 (18)	1.09980 (17)	0.51432 (15)	0.0368 (5)
O4	1.2155 (2)	1.1457 (2)	0.6103 (2)	0.0560 (7)
O5	0.4273 (2)	0.6234 (2)	0.13609 (17)	0.0475 (6)
O6	0.3230 (2)	0.7032 (2)	0.0151 (2)	0.0595 (8)
O7	0.37852 (18)	0.90204 (17)	0.06564 (15)	0.0365 (5)
O8	0.2890 (2)	0.8559 (2)	0.18645 (19)	0.0589 (8)
O9	0.3861 (3)	1.1764 (2)	0.32936 (18)	0.0681 (9)
H9	0.3631	1.2253	0.3498	0.102*
O10	0.1528 (3)	0.7960 (3)	−0.1033 (3)	0.1048 (15)
H10	0.2089	0.7617	−0.0737	0.157*
Co1	1.06880 (4)	1.25153 (3)	0.48469 (3)	0.03204 (13)
Co2	0.46122 (3)	0.75731 (3)	0.10263 (3)	0.03035 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0354 (18)	0.0329 (18)	0.0290 (17)	−0.0080 (14)	0.0011 (13)	−0.0136 (14)
C2	0.045 (2)	0.048 (2)	0.043 (2)	−0.0195 (17)	0.0080 (16)	−0.0191 (17)
C3	0.066 (3)	0.061 (3)	0.046 (2)	−0.030 (2)	0.0047 (19)	−0.029 (2)
C4	0.077 (3)	0.072 (3)	0.046 (3)	−0.035 (2)	0.015 (2)	−0.035 (2)
C5	0.063 (3)	0.058 (3)	0.036 (2)	−0.025 (2)	0.0161 (17)	−0.0238 (19)
C6	0.0398 (19)	0.0355 (19)	0.0314 (18)	−0.0102 (14)	0.0019 (14)	−0.0127 (15)
C7	0.0295 (17)	0.0269 (16)	0.0295 (17)	−0.0062 (12)	0.0030 (12)	−0.0086 (13)
C8	0.0357 (18)	0.0335 (18)	0.0359 (19)	−0.0092 (14)	−0.0005 (14)	−0.0141 (15)
C9	0.0297 (17)	0.0374 (19)	0.0323 (18)	−0.0097 (13)	0.0034 (13)	−0.0159 (15)
C10	0.0333 (18)	0.0341 (18)	0.0318 (18)	−0.0087 (13)	0.0029 (13)	−0.0130 (14)
C11	0.0388 (19)	0.0349 (19)	0.0291 (18)	−0.0102 (14)	0.0046 (13)	−0.0128 (14)
C12	0.0381 (19)	0.0324 (18)	0.0239 (17)	−0.0087 (14)	0.0025 (13)	−0.0081 (14)
C13	0.0361 (19)	0.0265 (17)	0.0351 (19)	−0.0022 (13)	0.0061 (14)	−0.0004 (14)
C14	0.054 (2)	0.034 (2)	0.040 (2)	−0.0035 (16)	0.0089 (17)	−0.0047 (16)
C15	0.060 (3)	0.036 (2)	0.058 (3)	0.0092 (18)	0.015 (2)	0.0007 (19)
C16	0.046 (2)	0.049 (3)	0.058 (3)	0.0094 (19)	0.001 (2)	0.004 (2)
C17	0.048 (2)	0.056 (3)	0.046 (2)	−0.0010 (19)	−0.0079 (18)	0.001 (2)
C18	0.041 (2)	0.039 (2)	0.037 (2)	−0.0030 (15)	−0.0016 (15)	−0.0029 (16)
C19	0.0402 (19)	0.0290 (18)	0.0267 (17)	−0.0062 (14)	0.0001 (13)	−0.0044 (14)
C20	0.060 (2)	0.039 (2)	0.0283 (19)	−0.0105 (17)	−0.0053 (16)	−0.0102 (16)
C21	0.069 (3)	0.047 (2)	0.0276 (19)	−0.0156 (19)	0.0076 (17)	−0.0077 (17)
C22	0.050 (2)	0.047 (2)	0.038 (2)	−0.0178 (17)	0.0074 (16)	−0.0080 (17)
C23	0.039 (2)	0.039 (2)	0.0321 (19)	−0.0109 (15)	−0.0006 (14)	−0.0086 (15)
C24	0.0324 (18)	0.0272 (17)	0.0266 (17)	−0.0042 (13)	−0.0010 (13)	−0.0058 (13)
C25	0.0319 (17)	0.0256 (17)	0.0321 (18)	−0.0042 (12)	−0.0016 (13)	−0.0108 (14)
C26	0.0356 (19)	0.0361 (19)	0.0341 (18)	−0.0094 (14)	0.0047 (14)	−0.0136 (15)
C27	0.0340 (18)	0.0304 (17)	0.0288 (17)	−0.0077 (13)	−0.0001 (13)	−0.0062 (14)
C28	0.0338 (18)	0.0343 (18)	0.0271 (17)	−0.0088 (14)	0.0029 (13)	−0.0079 (14)
C29	0.0395 (19)	0.0314 (18)	0.0280 (18)	−0.0051 (14)	−0.0038 (13)	−0.0094 (14)
C30	0.0364 (18)	0.0296 (17)	0.0310 (18)	−0.0081 (13)	0.0011 (13)	−0.0119 (14)
C31	0.0393 (19)	0.0266 (17)	0.0366 (19)	−0.0074 (14)	0.0039 (14)	−0.0133 (14)
C32	0.047 (2)	0.049 (2)	0.045 (2)	−0.0099 (17)	0.0112 (17)	−0.0193 (18)
C33	0.036 (2)	0.058 (3)	0.061 (3)	0.0026 (18)	0.0038 (18)	−0.025 (2)
C34	0.049 (2)	0.051 (2)	0.047 (2)	0.0044 (18)	−0.0128 (18)	−0.0200 (19)
C35	0.041 (2)	0.040 (2)	0.0333 (19)	0.0004 (15)	−0.0043 (14)	−0.0161 (16)
C36	0.0375 (18)	0.0287 (17)	0.0306 (18)	−0.0056 (13)	−0.0012 (13)	−0.0140 (14)
C37	0.036 (2)	0.037 (2)	0.036 (2)	−0.0086 (15)	−0.0019 (15)	−0.0059 (16)
C38	0.052 (2)	0.048 (2)	0.058 (3)	−0.0216 (19)	0.0111 (19)	−0.006 (2)
C39	0.0315 (18)	0.045 (2)	0.0308 (18)	−0.0110 (15)	0.0016 (13)	−0.0147 (15)
C40	0.046 (2)	0.056 (3)	0.049 (2)	−0.0014 (18)	−0.0098 (18)	−0.006 (2)
C41	0.066 (3)	0.048 (2)	0.043 (2)	−0.027 (2)	−0.0009 (19)	−0.0145 (19)
C42	0.165 (6)	0.068 (4)	0.091 (4)	−0.071 (4)	−0.027 (4)	−0.018 (3)
C43	0.0294 (18)	0.043 (2)	0.0331 (19)	−0.0089 (14)	0.0015 (13)	−0.0125 (15)
C44	0.064 (3)	0.049 (3)	0.062 (3)	0.007 (2)	0.007 (2)	−0.022 (2)
C45	0.067 (3)	0.059 (3)	0.035 (2)	0.002 (2)	−0.0014 (19)	−0.010 (2)
C46	0.072 (3)	0.065 (3)	0.046 (3)	−0.012 (2)	0.007 (2)	−0.017 (2)
C47	0.186 (10)	0.303 (15)	0.075 (6)	0.144 (10)	−0.027 (6)	0.002 (7)
C48	0.148 (8)	0.386 (18)	0.302 (15)	−0.185 (11)	0.125 (9)	−0.285 (15)
N1	0.0359 (15)	0.0321 (15)	0.0299 (15)	−0.0097 (12)	0.0036 (11)	−0.0125 (12)
N2	0.0374 (16)	0.0341 (16)	0.0361 (16)	−0.0169 (12)	0.0095 (12)	−0.0133 (13)
N3	0.0333 (15)	0.0317 (15)	0.0274 (14)	−0.0045 (11)	0.0022 (11)	−0.0070 (12)
N4	0.0449 (18)	0.0438 (18)	0.0364 (17)	−0.0032 (14)	−0.0084 (13)	−0.0130 (14)
N5	0.0315 (15)	0.0277 (14)	0.0258 (14)	−0.0062 (11)	−0.0015 (10)	−0.0076 (11)
N6	0.0358 (15)	0.0352 (16)	0.0320 (15)	−0.0127 (12)	−0.0064 (11)	−0.0111 (12)
N7	0.0338 (15)	0.0287 (15)	0.0271 (15)	−0.0022 (11)	−0.0027 (11)	−0.0086 (12)
N8	0.0466 (18)	0.0342 (16)	0.0256 (15)	−0.0060 (13)	0.0022 (12)	−0.0076 (12)
O1	0.0512 (16)	0.0465 (16)	0.0476 (16)	−0.0206 (12)	0.0158 (12)	−0.0187 (12)
O2	0.0478 (16)	0.0427 (16)	0.0630 (18)	−0.0097 (12)	0.0072 (13)	−0.0246 (14)
O3	0.0434 (14)	0.0373 (14)	0.0296 (13)	−0.0055 (10)	−0.0049 (10)	−0.0130 (10)
O4	0.0508 (17)	0.068 (2)	0.0643 (19)	−0.0211 (14)	−0.0051 (13)	−0.0362 (16)
O5	0.0626 (17)	0.0469 (16)	0.0399 (15)	−0.0239 (13)	−0.0042 (12)	−0.0136 (12)
O6	0.0633 (19)	0.0606 (19)	0.0536 (18)	−0.0239 (15)	−0.0142 (14)	−0.0053 (15)
O7	0.0400 (14)	0.0356 (13)	0.0303 (13)	−0.0036 (10)	0.0041 (10)	−0.0096 (10)
O8	0.0490 (17)	0.0653 (19)	0.0511 (18)	−0.0162 (14)	0.0165 (13)	0.0015 (15)
O9	0.090 (2)	0.0602 (19)	0.0334 (16)	0.0070 (16)	0.0208 (15)	−0.0070 (14)
O10	0.077 (2)	0.156 (4)	0.077 (3)	0.021 (2)	−0.032 (2)	−0.066 (3)
Co1	0.0368 (3)	0.0332 (3)	0.0288 (3)	−0.00936 (19)	0.00475 (18)	−0.0129 (2)
Co2	0.0345 (3)	0.0311 (3)	0.0252 (2)	−0.00629 (18)	−0.00124 (17)	−0.00913 (18)

Geometric parameters (Å, º)

C1—C2	1.383 (5)	C30—N7	1.323 (4)
C1—C6	1.395 (5)	C30—N8	1.352 (4)
C1—N1	1.403 (4)	C31—N8	1.372 (4)
C2—C3	1.380 (5)	C31—C32	1.383 (5)
C2—H2	0.9300	C31—C36	1.397 (4)
C3—C4	1.397 (5)	C32—C33	1.368 (6)
C3—H3	0.9300	C32—H32	0.9300
C4—C5	1.378 (5)	C33—C34	1.397 (6)
C4—H4	0.9300	C33—H33	0.9300
C5—C6	1.385 (5)	C34—C35	1.379 (5)
C5—H5	0.9300	C34—H34	0.9300
C6—N2	1.374 (4)	C35—C36	1.382 (5)
C7—N1	1.332 (4)	C35—H35	0.9300
C7—N2	1.343 (4)	C36—N7	1.404 (4)
C7—C8	1.488 (4)	C37—O1	1.252 (4)
C8—C9	1.523 (5)	C37—O2	1.253 (4)
C8—H8A	0.9700	C37—C38	1.503 (5)
C8—H8B	0.9700	C38—H38A	0.9600
C9—C10	1.520 (4)	C38—H38B	0.9600
C9—H9A	0.9700	C38—H38C	0.9600
C9—H9B	0.9700	C39—O4	1.241 (4)
C10—C11	1.529 (4)	C39—O3	1.270 (4)
C10—H10A	0.9700	C39—C40	1.488 (5)
C10—H10B	0.9700	C40—H40A	0.9600
C11—C12	1.490 (4)	C40—H40B	0.9600
C11—H11A	0.9700	C40—H40C	0.9600
C11—H11B	0.9700	C41—O6	1.238 (5)
C12—N3	1.324 (4)	C41—O5	1.259 (4)
C12—N4	1.353 (4)	C41—C42	1.494 (6)
C13—C18	1.391 (5)	C42—H42A	0.9600
C13—N3	1.395 (4)	C42—H42B	0.9600
C13—C14	1.398 (5)	C42—H42C	0.9600
C14—C15	1.382 (5)	C43—O8	1.236 (4)
C14—H14	0.9300	C43—O7	1.266 (4)
C15—C16	1.393 (6)	C43—C44	1.501 (5)
C15—H15	0.9300	C44—H44A	0.9600
C16—C17	1.369 (6)	C44—H44B	0.9600
C16—H16	0.9300	C44—H44C	0.9600
C17—C18	1.391 (5)	C45—O9	1.391 (5)
C17—H17	0.9300	C45—C46	1.491 (6)
C18—N4	1.378 (5)	C45—H45A	0.9700
C19—N6	1.379 (4)	C45—H45B	0.9700
C19—C24	1.380 (4)	C46—H46A	0.9600
C19—C20	1.393 (5)	C46—H46B	0.9600
C20—C21	1.371 (5)	C46—H46C	0.9600
C20—H20	0.9300	C47—O10	1.431 (10)
C21—C22	1.399 (5)	C47—C48	1.440 (12)
C21—H21	0.9300	C47—H47A	0.9700
C22—C23	1.385 (5)	C47—H47B	0.9700
C22—H22	0.9300	C48—H48A	0.9600
C23—C24	1.399 (5)	C48—H48B	0.9600
C23—H23	0.9300	C48—H48C	0.9600
C24—N5	1.402 (4)	N1—Co1	2.055 (3)
C25—N5	1.335 (4)	N2—H2A	0.8600
C25—N6	1.341 (4)	N3—Co1^i	2.063 (3)
C25—C26	1.481 (4)	N4—H4A	0.8600
C26—C27	1.525 (4)	N5—Co2	2.045 (3)
C26—H26A	0.9700	N6—H6	0.8600
C26—H26B	0.9700	N7—Co2^ii	2.053 (3)
C27—C28	1.514 (4)	N8—H8	0.8600
C27—H27A	0.9700	O1—Co1	2.006 (2)
C27—H27B	0.9700	O3—Co1	2.005 (2)
C28—C29	1.527 (4)	O5—Co2	1.966 (3)
C28—H28A	0.9700	O7—Co2	1.969 (2)
C28—H28B	0.9700	O9—H9	0.8200
C29—C30	1.482 (4)	O10—H10	0.8200
C29—H29A	0.9700	Co1—N3^i	2.063 (3)
C29—H29B	0.9700	Co2—N7^ii	2.053 (3)
C2—C1—C6	120.7 (3)	C33—C32—C31	116.5 (4)
C2—C1—N1	130.7 (3)	C33—C32—H32	121.7
C6—C1—N1	108.6 (3)	C31—C32—H32	121.7
C3—C2—C1	117.1 (3)	C32—C33—C34	121.8 (4)
C3—C2—H2	121.5	C32—C33—H33	119.1
C1—C2—H2	121.5	C34—C33—H33	119.1
C2—C3—C4	121.8 (4)	C35—C34—C33	121.6 (4)
C2—C3—H3	119.1	C35—C34—H34	119.2
C4—C3—H3	119.1	C33—C34—H34	119.2
C5—C4—C3	121.5 (4)	C34—C35—C36	117.0 (3)
C5—C4—H4	119.2	C34—C35—H35	121.5
C3—C4—H4	119.2	C36—C35—H35	121.5
C4—C5—C6	116.3 (3)	C35—C36—C31	120.7 (3)
C4—C5—H5	121.8	C35—C36—N7	130.1 (3)
C6—C5—H5	121.8	C31—C36—N7	109.2 (3)
N2—C6—C5	131.6 (3)	O1—C37—O2	120.6 (3)
N2—C6—C1	105.9 (3)	O1—C37—C38	118.8 (3)
C5—C6—C1	122.5 (3)	O2—C37—C38	120.6 (3)
N1—C7—N2	112.0 (3)	C37—C38—H38A	109.5
N1—C7—C8	125.7 (3)	C37—C38—H38B	109.5
N2—C7—C8	122.2 (3)	H38A—C38—H38B	109.5
C7—C8—C9	114.5 (3)	C37—C38—H38C	109.5
C7—C8—H8A	108.6	H38A—C38—H38C	109.5
C9—C8—H8A	108.6	H38B—C38—H38C	109.5
C7—C8—H8B	108.6	O4—C39—O3	120.2 (3)
C9—C8—H8B	108.6	O4—C39—C40	121.8 (3)
H8A—C8—H8B	107.6	O3—C39—C40	118.0 (3)
C10—C9—C8	113.7 (3)	C39—C40—H40A	109.5
C10—C9—H9A	108.8	C39—C40—H40B	109.5
C8—C9—H9A	108.8	H40A—C40—H40B	109.5
C10—C9—H9B	108.8	C39—C40—H40C	109.5
C8—C9—H9B	108.8	H40A—C40—H40C	109.5
H9A—C9—H9B	107.7	H40B—C40—H40C	109.5
C9—C10—C11	111.3 (3)	O6—C41—O5	121.5 (4)
C9—C10—H10A	109.4	O6—C41—C42	120.7 (4)
C11—C10—H10A	109.4	O5—C41—C42	117.7 (4)
C9—C10—H10B	109.4	C41—C42—H42A	109.5
C11—C10—H10B	109.4	C41—C42—H42B	109.5
H10A—C10—H10B	108.0	H42A—C42—H42B	109.5
C12—C11—C10	112.9 (3)	C41—C42—H42C	109.5
C12—C11—H11A	109.0	H42A—C42—H42C	109.5
C10—C11—H11A	109.0	H42B—C42—H42C	109.5
C12—C11—H11B	109.0	O8—C43—O7	121.6 (3)
C10—C11—H11B	109.0	O8—C43—C44	121.7 (3)
H11A—C11—H11B	107.8	O7—C43—C44	116.7 (3)
N3—C12—N4	111.6 (3)	C43—C44—H44A	109.5
N3—C12—C11	125.1 (3)	C43—C44—H44B	109.5
N4—C12—C11	123.2 (3)	H44A—C44—H44B	109.5
C18—C13—N3	109.4 (3)	C43—C44—H44C	109.5
C18—C13—C14	120.0 (3)	H44A—C44—H44C	109.5
N3—C13—C14	130.6 (3)	H44B—C44—H44C	109.5
C15—C14—C13	117.0 (4)	O9—C45—C46	111.2 (3)
C15—C14—H14	121.5	O9—C45—H45A	109.4
C13—C14—H14	121.5	C46—C45—H45A	109.4
C14—C15—C16	122.1 (4)	O9—C45—H45B	109.4
C14—C15—H15	118.9	C46—C45—H45B	109.4
C16—C15—H15	118.9	H45A—C45—H45B	108.0
C17—C16—C15	121.4 (4)	C45—C46—H46A	109.5
C17—C16—H16	119.3	C45—C46—H46B	109.5
C15—C16—H16	119.3	H46A—C46—H46B	109.5
C16—C17—C18	116.8 (4)	C45—C46—H46C	109.5
C16—C17—H17	121.6	H46A—C46—H46C	109.5
C18—C17—H17	121.6	H46B—C46—H46C	109.5
N4—C18—C17	132.2 (4)	O10—C47—C48	104.8 (8)
N4—C18—C13	105.1 (3)	O10—C47—H47A	110.8
C17—C18—C13	122.6 (4)	C48—C47—H47A	110.8
N6—C19—C24	105.8 (3)	O10—C47—H47B	110.8
N6—C19—C20	131.5 (3)	C48—C47—H47B	110.8
C24—C19—C20	122.7 (3)	H47A—C47—H47B	108.9
C21—C20—C19	116.5 (3)	C47—C48—H48A	109.5
C21—C20—H20	121.7	C47—C48—H48B	109.5
C19—C20—H20	121.7	H48A—C48—H48B	109.5
C20—C21—C22	121.4 (3)	C47—C48—H48C	109.5
C20—C21—H21	119.3	H48A—C48—H48C	109.5
C22—C21—H21	119.3	H48B—C48—H48C	109.5
C23—C22—C21	122.0 (3)	C7—N1—C1	105.3 (3)
C23—C22—H22	119.0	C7—N1—Co1	127.7 (2)
C21—C22—H22	119.0	C1—N1—Co1	125.6 (2)
C22—C23—C24	116.6 (3)	C7—N2—C6	108.2 (3)
C22—C23—H23	121.7	C7—N2—H2A	125.9
C24—C23—H23	121.7	C6—N2—H2A	125.9
C19—C24—C23	120.7 (3)	C12—N3—C13	105.6 (3)
C19—C24—N5	109.0 (3)	C12—N3—Co1^i	128.6 (2)
C23—C24—N5	130.3 (3)	C13—N3—Co1^i	125.7 (2)
N5—C25—N6	111.5 (3)	C12—N4—C18	108.3 (3)
N5—C25—C26	125.8 (3)	C12—N4—H4A	125.9
N6—C25—C26	122.6 (3)	C18—N4—H4A	125.9
C25—C26—C27	112.5 (3)	C25—N5—C24	105.3 (3)
C25—C26—H26A	109.1	C25—N5—Co2	129.7 (2)
C27—C26—H26A	109.1	C24—N5—Co2	123.5 (2)
C25—C26—H26B	109.1	C25—N6—C19	108.3 (3)
C27—C26—H26B	109.1	C25—N6—H6	125.8
H26A—C26—H26B	107.8	C19—N6—H6	125.8
C28—C27—C26	112.7 (3)	C30—N7—C36	105.2 (3)
C28—C27—H27A	109.0	C30—N7—Co2^ii	126.5 (2)
C26—C27—H27A	109.0	C36—N7—Co2^ii	128.2 (2)
C28—C27—H27B	109.0	C30—N8—C31	108.4 (3)
C26—C27—H27B	109.0	C30—N8—H8	125.8
H27A—C27—H27B	107.8	C31—N8—H8	125.8
C27—C28—C29	111.7 (3)	C37—O1—Co1	101.7 (2)
C27—C28—H28A	109.3	C39—O3—Co1	105.6 (2)
C29—C28—H28A	109.3	C41—O5—Co2	107.4 (2)
C27—C28—H28B	109.3	C43—O7—Co2	112.1 (2)
C29—C28—H28B	109.3	C45—O9—H9	109.5
H28A—C28—H28B	107.9	C47—O10—H10	109.5
C30—C29—C28	112.9 (3)	O3—Co1—O1	138.91 (10)
C30—C29—H29A	109.0	O3—Co1—N1	99.63 (11)
C28—C29—H29A	109.0	O1—Co1—N1	102.51 (10)
C30—C29—H29B	109.0	O3—Co1—N3^i	100.38 (10)
C28—C29—H29B	109.0	O1—Co1—N3^i	106.23 (11)
H29A—C29—H29B	107.8	N1—Co1—N3^i	105.72 (10)
N7—C30—N8	112.0 (3)	O5—Co2—O7	136.66 (11)
N7—C30—C29	126.1 (3)	O5—Co2—N5	100.24 (11)
N8—C30—C29	121.9 (3)	O7—Co2—N5	103.01 (10)
N8—C31—C32	132.6 (3)	O5—Co2—N7^ii	103.71 (11)
N8—C31—C36	105.2 (3)	O7—Co2—N7^ii	100.22 (10)
C32—C31—C36	122.2 (3)	N5—Co2—N7^ii	112.80 (10)
C6—C1—C2—C3	0.8 (5)	C1—C6—N2—C7	−0.6 (4)
N1—C1—C2—C3	179.1 (4)	N4—C12—N3—C13	0.6 (4)
C1—C2—C3—C4	−0.2 (6)	C11—C12—N3—C13	177.9 (3)
C2—C3—C4—C5	−0.6 (7)	N4—C12—N3—Co1^i	−176.8 (2)
C3—C4—C5—C6	0.8 (7)	C11—C12—N3—Co1^i	0.5 (5)
C4—C5—C6—N2	−179.7 (4)	C18—C13—N3—C12	−0.5 (4)
C4—C5—C6—C1	−0.1 (6)	C14—C13—N3—C12	178.9 (4)
C2—C1—C6—N2	179.0 (3)	C18—C13—N3—Co1^i	177.0 (2)
N1—C1—C6—N2	0.4 (4)	C14—C13—N3—Co1^i	−3.7 (5)
C2—C1—C6—C5	−0.7 (5)	N3—C12—N4—C18	−0.4 (4)
N1—C1—C6—C5	−179.3 (3)	C11—C12—N4—C18	−177.8 (3)
N1—C7—C8—C9	136.3 (3)	C17—C18—N4—C12	179.5 (4)
N2—C7—C8—C9	−46.1 (4)	C13—C18—N4—C12	0.1 (4)
C7—C8—C9—C10	−73.2 (4)	N6—C25—N5—C24	0.1 (3)
C8—C9—C10—C11	−175.9 (3)	C26—C25—N5—C24	−179.1 (3)
C9—C10—C11—C12	161.3 (3)	N6—C25—N5—Co2	166.3 (2)
C10—C11—C12—N3	−93.1 (4)	C26—C25—N5—Co2	−12.9 (5)
C10—C11—C12—N4	83.9 (4)	C19—C24—N5—C25	−0.1 (3)
C18—C13—C14—C15	−1.6 (5)	C23—C24—N5—C25	−178.3 (3)
N3—C13—C14—C15	179.1 (3)	C19—C24—N5—Co2	−167.4 (2)
C13—C14—C15—C16	0.8 (6)	C23—C24—N5—Co2	14.4 (5)
C14—C15—C16—C17	0.3 (7)	N5—C25—N6—C19	0.0 (4)
C15—C16—C17—C18	−0.6 (6)	C26—C25—N6—C19	179.2 (3)
C16—C17—C18—N4	−179.5 (4)	C24—C19—N6—C25	−0.1 (3)
C16—C17—C18—C13	−0.2 (6)	C20—C19—N6—C25	−179.6 (4)
N3—C13—C18—N4	0.3 (4)	N8—C30—N7—C36	0.8 (4)
C14—C13—C18—N4	−179.2 (3)	C29—C30—N7—C36	178.0 (3)
N3—C13—C18—C17	−179.2 (3)	N8—C30—N7—Co2^ii	177.1 (2)
C14—C13—C18—C17	1.3 (6)	C29—C30—N7—Co2^ii	−5.7 (5)
N6—C19—C20—C21	−179.4 (4)	C35—C36—N7—C30	177.5 (3)
C24—C19—C20—C21	1.2 (5)	C31—C36—N7—C30	−1.5 (3)
C19—C20—C21—C22	0.1 (6)	C35—C36—N7—Co2^ii	1.3 (5)
C20—C21—C22—C23	−0.8 (6)	C31—C36—N7—Co2^ii	−177.7 (2)
C21—C22—C23—C24	0.2 (5)	N7—C30—N8—C31	0.2 (4)
N6—C19—C24—C23	178.6 (3)	C29—C30—N8—C31	−177.1 (3)
C20—C19—C24—C23	−1.9 (5)	C32—C31—N8—C30	−179.3 (4)
N6—C19—C24—N5	0.2 (4)	C36—C31—N8—C30	−1.1 (4)
C20—C19—C24—N5	179.7 (3)	O2—C37—O1—Co1	−2.7 (4)
C22—C23—C24—C19	1.1 (5)	C38—C37—O1—Co1	176.7 (3)
C22—C23—C24—N5	179.1 (3)	O4—C39—O3—Co1	−5.0 (4)
N5—C25—C26—C27	123.7 (3)	C40—C39—O3—Co1	174.5 (3)
N6—C25—C26—C27	−55.4 (4)	O6—C41—O5—Co2	−6.7 (5)
C25—C26—C27—C28	−62.3 (4)	C42—C41—O5—Co2	171.8 (4)
C26—C27—C28—C29	−177.4 (3)	O8—C43—O7—Co2	−7.0 (4)
C27—C28—C29—C30	168.8 (3)	C44—C43—O7—Co2	172.1 (3)
C28—C29—C30—N7	−89.5 (4)	C39—O3—Co1—O1	50.1 (3)
C28—C29—C30—N8	87.4 (4)	C39—O3—Co1—N1	−71.8 (2)
N8—C31—C32—C33	177.8 (4)	C39—O3—Co1—N3^i	−179.9 (2)
C36—C31—C32—C33	−0.1 (5)	C37—O1—Co1—O3	53.4 (3)
C31—C32—C33—C34	−1.2 (6)	C37—O1—Co1—N1	174.5 (2)
C32—C33—C34—C35	1.8 (6)	C37—O1—Co1—N3^i	−74.8 (2)
C33—C34—C35—C36	−0.9 (6)	C7—N1—Co1—O3	−53.1 (3)
C34—C35—C36—C31	−0.4 (5)	C1—N1—Co1—O3	111.7 (3)
C34—C35—C36—N7	−179.3 (3)	C7—N1—Co1—O1	161.7 (3)
N8—C31—C36—C35	−177.5 (3)	C1—N1—Co1—O1	−33.5 (3)
C32—C31—C36—C35	1.0 (5)	C7—N1—Co1—N3^i	50.6 (3)
N8—C31—C36—N7	1.6 (3)	C1—N1—Co1—N3^i	−144.5 (3)
C32—C31—C36—N7	−179.9 (3)	C41—O5—Co2—O7	49.7 (3)
N2—C7—N1—C1	−0.3 (4)	C41—O5—Co2—N5	171.4 (3)
C8—C7—N1—C1	177.6 (3)	C41—O5—Co2—N7^ii	−71.9 (3)
N2—C7—N1—Co1	167.0 (2)	C43—O7—Co2—O5	54.8 (3)
C8—C7—N1—Co1	−15.2 (5)	C43—O7—Co2—N5	−65.9 (2)
C2—C1—N1—C7	−178.5 (4)	C43—O7—Co2—N7^ii	177.7 (2)
C6—C1—N1—C7	−0.1 (4)	C25—N5—Co2—O5	148.2 (3)
C2—C1—N1—Co1	13.9 (5)	C24—N5—Co2—O5	−47.8 (3)
C6—C1—N1—Co1	−167.7 (2)	C25—N5—Co2—O7	−68.6 (3)
N1—C7—N2—C6	0.5 (4)	C24—N5—Co2—O7	95.4 (2)
C8—C7—N2—C6	−177.4 (3)	C25—N5—Co2—N7^ii	38.5 (3)
C5—C6—N2—C7	179.1 (4)	C24—N5—Co2—N7^ii	−157.5 (2)

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O8^iii	0.86	1.87	2.707 (4)	166
N4—H4A···O10^iv	0.86	1.93	2.780 (4)	170
N8—H8···O9	0.86	1.87	2.720 (4)	167
N6—H6···O4^i	0.86	1.87	2.719 (4)	172
O9—H9···O2^v	0.82	2.03	2.636 (4)	130
O10—H10···O6	0.82	1.89	2.687 (4)	165

Symmetry codes: (i) −x+2, −y+2, −z+1; (iii) −x+1, −y+2, −z+1; (iv) x+1, y, z+1; (v) x−1, y, z.