Two Co^II coordination polymers of biphenyl-2,2′,5,5′-tetra­carb­oxy­lic acid with flexible N-donor ligands: syntheses, structures and magnetic properties

Two Co^II-based coordination polymers, namely poly[(μ₄-biphenyl-2,2′,5,5′-tetra­carboxyl­ato){μ₂-1,3-bis­[(1H-imidazol-1-yl)meth­yl]benzene}­dicobalt(II)], [Co₂(C₁₆H₆O₈)(C₁₄H₁₄N₄)₂]_n or [Co₂(o,m-bpta)(1,3-bimb)₂]_n (I), and poly[[aqua­(μ₄-biphenyl-2,2′,5,5′-tetra­carboxyl­ato){1,4-bis­[(1H-imidazol-1-yl)meth­yl]benzene}­dicobalt(II)] dihydrate], {[Co₂(C₁₆H₆O₈)(C₁₄H₁₄N₄)₂(H₂O)₂]·4H₂O}_n or {[Co₂(o,m-bpta)(1,4-bimb)₂(H₂O)₂]·4H₂O}_n (II), were synthesized from a mix­ture of biphenyl-2,2′,5,5′-tetra­carb­oxy­lic acid, i.e. [H₄(o,m-bpta)], CoCl₂·6H₂O and N-donor ligands under solvothermal conditions. The complexes were char­acterized by IR spectroscopy, elemental analysis, single-crystal X-ray diffraction and powder X-ray diffraction analysis. The bridging (o,m-bpta)⁴⁻ ligands combine with Co^II ions in different μ₄-coordination modes, leading to the formation of one-dimensional chains. The central Co^II atoms display tetra­hedral [CoN₂O₂] and octa­hedral [CoN₂O₄] geometries in I and II, respectively. The bis­[(1H-imidazol-1-yl)meth­yl]benzene (bimb) ligands adopt trans or cis conformations to connect Co^II ions, thus forming two three-dimensional (3D) networks. Complex I shows a (2,4)-connected 3D network with left- and right-handed helical chains constructed by (o,m-bpta)⁴⁻ ligands. Complex II is a (4,4)-connected 3D novel network with ribbon-like chains formed by (o,m-bpta)⁴⁻ linkers. Magnetic studies indicate an orbital contribution to the magnetic moment of I and II due to the longer Co...Co distances. An attempt has been made to fit the χ_MT results to the magnetic formulae for mononuclear Co^II complexes, the fitting indicating the presence of weak anti­ferromagnetic inter­actions between the Co^II ions.

Computing details

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2005) and PLATON (Spek, 2009); software used to prepare material for publication: pubCIF (Westrip, 2010).

Poly[(µ₄-biphenyl-2,2',5,5'-tetracarboxylato){µ₂-1,3-bis[(1H-imidazol-1-yl)methyl]benzene}dicobalt(II)] (sf180123-7)

Crystal data

[Co2(C16H6O8)(C14H14N4)2]	F(000) = 944
Mr = 920.65	Dx = 1.535 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 10.4597 (9) Å	Cell parameters from 2201 reflections
b = 12.7980 (6) Å	θ = 2.2–19.5°
c = 15.0545 (9) Å	µ = 0.90 mm^−1
β = 98.709 (5)°	T = 296 K
V = 1992.0 (2) Å^3	Block, blue
Z = 2	0.32 × 0.30 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer	5115 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.089
φ and ω scans	θmax = 27.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −13→13
Tmin = 0.680, Tmax = 0.746	k = −16→16
24855 measured reflections	l = −19→19
8869 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.068	w = 1/[σ^2(Fo^2) + (0.0831P)^2 + 0.0494P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.183	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.69 e Å^−3
8869 reflections	Δρmin = −0.34 e Å^−3
559 parameters	Absolute structure: Flack x determined using 1721 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
83 restraints	Absolute structure parameter: 0.059 (17)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Co1	0.74945 (8)	0.91204 (7)	0.71858 (6)	0.0390 (2)
Co2	0.36031 (9)	0.57480 (7)	1.29195 (6)	0.0419 (3)
O1	0.7780 (5)	0.8668 (5)	0.8484 (3)	0.0581 (16)
O2	0.5816 (6)	0.8354 (5)	0.7893 (4)	0.0701 (19)
O3	0.4067 (5)	0.6172 (4)	1.1728 (3)	0.0498 (15)
O4	0.6078 (5)	0.6236 (5)	1.2424 (3)	0.0610 (17)
O5	0.8102 (5)	0.5359 (4)	0.9502 (3)	0.0449 (14)
O6	0.9357 (5)	0.5552 (4)	0.8445 (3)	0.0513 (14)
O7	1.1278 (6)	0.9767 (4)	1.1657 (4)	0.0620 (17)
O8	1.2285 (6)	0.9886 (5)	1.0496 (5)	0.0789 (19)
N1	0.7432 (6)	0.7821 (4)	0.6444 (4)	0.0442 (14)
N2	0.7580 (7)	0.6850 (4)	0.5255 (4)	0.0525 (19)
N3	0.6417 (7)	1.0092 (5)	0.2610 (5)	0.0591 (14)
N4	0.4358 (7)	1.0329 (5)	0.2218 (5)	0.059 (2)
N5	0.1696 (6)	0.5516 (4)	1.2561 (4)	0.0436 (17)
N6	−0.0314 (6)	0.4960 (5)	1.2513 (4)	0.0438 (17)
N7	−0.1214 (6)	0.1896 (4)	0.9838 (4)	0.0462 (17)
N8	−0.1150 (6)	0.2956 (4)	0.8721 (4)	0.0405 (16)
C1	0.7361 (6)	0.7440 (5)	1.0081 (4)	0.0322 (16)
C2	0.6447 (5)	0.7747 (4)	0.93636 (18)	0.0400 (19)
C3	0.5147 (7)	0.7535 (6)	0.9424 (5)	0.053 (2)
H3	0.451703	0.769692	0.893913	0.064*
C4	0.4767 (7)	0.7086 (6)	1.0192 (5)	0.051 (2)
H4	0.389570	0.695787	1.020708	0.061*
C5	0.5653 (4)	0.6838 (4)	1.09110 (18)	0.0360 (17)
C6	0.6977 (6)	0.7045 (5)	1.0865 (4)	0.0324 (17)
H6	0.759721	0.691451	1.136367	0.039*
C7	0.6700 (5)	0.8273 (4)	0.85228 (18)	0.0403 (19)
C8	0.5275 (4)	0.6403 (4)	1.17533 (18)	0.0416 (19)
C9	0.8803 (6)	0.7541 (5)	1.0063 (4)	0.0313 (16)
C10	0.9473 (5)	0.6835 (2)	0.9582 (3)	0.0375 (18)
C11	1.0755 (7)	0.7045 (5)	0.9510 (5)	0.0385 (18)
H11	1.120038	0.659957	0.917611	0.046*
C12	1.1382 (7)	0.7907 (5)	0.9925 (5)	0.044 (2)
H12	1.222721	0.805300	0.984301	0.053*
C13	1.0757 (6)	0.8559 (5)	1.0467 (5)	0.0380 (18)
C14	0.9469 (7)	0.8364 (5)	1.0523 (5)	0.0401 (19)
H14	0.903905	0.879585	1.087710	0.048*
C15	0.8909 (5)	0.5854 (2)	0.9152 (3)	0.0385 (18)
C16	1.1477 (8)	0.9479 (6)	1.0895 (6)	0.051 (2)
C17	0.7574 (8)	0.7810 (6)	0.5581 (5)	0.0507 (19)
H17	0.765839	0.840900	0.524518	0.061*
C18	0.7412 (8)	0.6808 (6)	0.6642 (5)	0.0573 (19)
H18	0.733487	0.654994	0.720904	0.069*
C19	0.7515 (9)	0.6206 (6)	0.5935 (6)	0.062 (3)
H19	0.753633	0.547968	0.592162	0.075*
C20	0.7709 (10)	0.6567 (7)	0.4326 (5)	0.073 (2)
H20A	0.685518	0.645868	0.398539	0.087*
H20B	0.818162	0.591432	0.432862	0.087*
C21	0.8395 (10)	0.7389 (7)	0.3878 (6)	0.0713 (16)
C22	0.9674 (10)	0.7341 (8)	0.3852 (7)	0.0832 (19)
H22	1.014678	0.677792	0.411857	0.100*
C23	1.0305 (10)	0.8117 (9)	0.3434 (7)	0.0887 (19)
H23	1.115721	0.801934	0.334355	0.106*
C24	0.9681 (10)	0.9005 (9)	0.3164 (7)	0.0856 (19)
H24	1.012555	0.954016	0.292490	0.103*
C25	0.8383 (9)	0.9136 (8)	0.3235 (7)	0.0766 (18)
C26	0.7764 (9)	0.8275 (7)	0.3576 (6)	0.0710 (18)
H26	0.688123	0.831890	0.359386	0.085*
C27	0.7710 (9)	1.0190 (7)	0.3116 (7)	0.073 (2)
H27A	0.765460	1.048697	0.370204	0.088*
H27B	0.821544	1.066137	0.280370	0.088*
C28	0.5319 (9)	1.0549 (6)	0.2800 (6)	0.063 (2)
H28	0.528049	1.097196	0.329776	0.076*
C29	0.4842 (9)	0.9713 (7)	0.1568 (7)	0.069 (2)
H29	0.436649	0.945304	0.104207	0.083*
C30	0.6138 (10)	0.9564 (7)	0.1846 (7)	0.0708 (18)
H30	0.670540	0.917410	0.155928	0.085*
C31	0.0875 (7)	0.5018 (5)	1.2984 (5)	0.0387 (18)
H31	0.109615	0.473243	1.355470	0.046*
C32	−0.0238 (8)	0.5470 (6)	1.1708 (5)	0.051 (2)
H32	−0.090342	0.555307	1.122843	0.062*
C33	0.0957 (8)	0.5814 (6)	1.1755 (5)	0.045 (2)
H33	0.126367	0.620300	1.130951	0.055*
C34	−0.1477 (8)	0.4551 (6)	1.2805 (5)	0.049 (2)
H34A	−0.208216	0.512167	1.282233	0.058*
H34B	−0.125210	0.428890	1.341320	0.058*
C35	−0.2145 (7)	0.3696 (6)	1.2232 (5)	0.042 (2)
C36	−0.3448 (7)	0.3585 (7)	1.2130 (5)	0.052 (2)
H36	−0.394041	0.403679	1.242453	0.062*
C37	−0.4065 (8)	0.2771 (7)	1.1569 (6)	0.063 (3)
H37	−0.496072	0.270496	1.148646	0.075*
C38	−0.3352 (9)	0.2104 (6)	1.1161 (5)	0.060 (3)
H38	−0.375641	0.155151	1.082962	0.072*
C39	−0.2048 (8)	0.2221 (5)	1.1224 (4)	0.042 (2)
C40	−0.1433 (7)	0.2986 (6)	1.1785 (5)	0.045 (2)
H40	−0.053519	0.303100	1.186806	0.053*
C41	−0.1244 (9)	0.1499 (6)	1.0745 (5)	0.062 (3)
H41A	−0.037169	0.146033	1.107127	0.074*
H41B	−0.161313	0.080270	1.071412	0.074*
C42	−0.1279 (8)	0.2891 (6)	0.9553 (5)	0.049 (2)
H42	−0.140214	0.346099	0.991357	0.059*
C43	−0.0956 (9)	0.1963 (6)	0.8427 (6)	0.064 (2)
H43	−0.080666	0.177422	0.785546	0.076*
C44	−0.1022 (9)	0.1306 (6)	0.9127 (6)	0.069 (3)
H44	−0.094875	0.058220	0.911815	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0527 (5)	0.0360 (4)	0.0295 (4)	0.0131 (5)	0.0095 (4)	0.0066 (4)
Co2	0.0563 (6)	0.0345 (4)	0.0354 (5)	0.0080 (5)	0.0087 (4)	0.0080 (4)
O1	0.054 (3)	0.080 (4)	0.041 (3)	−0.010 (3)	0.009 (2)	0.020 (3)
O2	0.068 (4)	0.097 (4)	0.045 (3)	−0.013 (4)	0.007 (3)	0.017 (3)
O3	0.053 (3)	0.055 (3)	0.041 (3)	0.000 (3)	0.008 (2)	0.012 (2)
O4	0.068 (4)	0.077 (4)	0.038 (3)	0.000 (3)	0.006 (3)	0.010 (3)
O5	0.052 (3)	0.040 (3)	0.045 (3)	−0.016 (2)	0.016 (2)	−0.011 (2)
O6	0.070 (3)	0.039 (3)	0.051 (3)	−0.014 (3)	0.029 (2)	−0.022 (2)
O7	0.073 (4)	0.057 (3)	0.059 (3)	−0.020 (3)	0.021 (3)	−0.023 (3)
O8	0.081 (4)	0.064 (4)	0.099 (4)	−0.040 (3)	0.036 (3)	−0.019 (3)
N1	0.064 (3)	0.036 (2)	0.033 (2)	0.010 (2)	0.010 (2)	0.006 (2)
N2	0.089 (5)	0.028 (3)	0.038 (3)	0.005 (3)	0.002 (3)	−0.003 (3)
N3	0.067 (3)	0.051 (2)	0.059 (3)	0.002 (2)	0.009 (2)	0.016 (2)
N4	0.067 (4)	0.040 (4)	0.070 (4)	−0.007 (3)	0.011 (4)	0.006 (3)
N5	0.056 (4)	0.028 (3)	0.044 (3)	0.006 (3)	−0.003 (3)	0.008 (3)
N6	0.055 (4)	0.042 (3)	0.031 (3)	−0.003 (3)	−0.002 (3)	−0.002 (3)
N7	0.061 (4)	0.033 (3)	0.048 (3)	0.009 (3)	0.019 (3)	−0.003 (3)
N8	0.044 (3)	0.034 (3)	0.045 (3)	−0.007 (3)	0.012 (3)	−0.010 (3)
C1	0.035 (3)	0.028 (3)	0.036 (3)	−0.007 (3)	0.011 (3)	−0.005 (3)
C2	0.034 (4)	0.043 (4)	0.045 (4)	0.005 (3)	0.012 (3)	0.002 (3)
C3	0.030 (4)	0.070 (5)	0.057 (5)	0.009 (4)	0.001 (4)	0.020 (4)
C4	0.028 (4)	0.064 (5)	0.065 (5)	0.016 (3)	0.018 (3)	0.022 (4)
C5	0.038 (4)	0.038 (4)	0.034 (3)	0.004 (3)	0.012 (3)	0.000 (3)
C6	0.027 (3)	0.039 (4)	0.032 (3)	0.000 (3)	0.006 (3)	−0.001 (3)
C7	0.029 (4)	0.062 (5)	0.030 (3)	0.008 (3)	0.003 (3)	0.003 (3)
C8	0.035 (4)	0.045 (4)	0.049 (4)	0.001 (3)	0.020 (3)	0.003 (3)
C9	0.031 (3)	0.041 (4)	0.022 (3)	−0.001 (3)	0.003 (3)	−0.003 (3)
C10	0.044 (4)	0.035 (4)	0.036 (3)	−0.005 (3)	0.014 (3)	0.000 (3)
C11	0.041 (4)	0.032 (3)	0.042 (4)	−0.001 (3)	0.007 (3)	−0.015 (3)
C12	0.034 (4)	0.043 (4)	0.059 (4)	−0.007 (3)	0.015 (3)	−0.001 (4)
C13	0.031 (3)	0.033 (3)	0.050 (4)	−0.001 (3)	0.008 (3)	−0.013 (3)
C14	0.048 (4)	0.034 (4)	0.039 (4)	−0.006 (3)	0.010 (3)	−0.005 (3)
C15	0.041 (4)	0.030 (3)	0.041 (4)	−0.007 (3)	−0.002 (3)	−0.011 (3)
C16	0.050 (4)	0.037 (4)	0.062 (5)	−0.012 (4)	−0.004 (4)	−0.004 (4)
C17	0.077 (4)	0.037 (3)	0.037 (3)	0.009 (3)	0.001 (3)	0.007 (3)
C18	0.082 (4)	0.048 (3)	0.046 (3)	0.004 (3)	0.021 (3)	0.013 (3)
C19	0.095 (6)	0.036 (4)	0.059 (5)	−0.008 (4)	0.024 (5)	0.004 (4)
C20	0.105 (4)	0.064 (4)	0.050 (4)	0.020 (4)	0.014 (4)	−0.006 (3)
C21	0.088 (3)	0.068 (3)	0.060 (3)	0.026 (3)	0.020 (3)	0.003 (3)
C22	0.089 (3)	0.082 (3)	0.079 (3)	0.033 (3)	0.012 (3)	0.000 (3)
C23	0.080 (3)	0.101 (4)	0.090 (3)	0.030 (3)	0.028 (3)	0.008 (3)
C24	0.074 (3)	0.102 (4)	0.087 (3)	0.016 (3)	0.033 (3)	0.020 (3)
C25	0.066 (3)	0.090 (3)	0.079 (3)	0.018 (3)	0.029 (3)	0.029 (3)
C26	0.071 (3)	0.077 (3)	0.070 (3)	0.025 (3)	0.028 (3)	0.022 (3)
C27	0.078 (4)	0.072 (4)	0.068 (4)	−0.006 (4)	0.004 (4)	0.013 (4)
C28	0.075 (4)	0.051 (4)	0.066 (4)	0.005 (3)	0.018 (3)	0.022 (3)
C29	0.075 (4)	0.060 (4)	0.075 (4)	0.004 (4)	0.018 (4)	0.012 (4)
C30	0.078 (3)	0.061 (3)	0.074 (3)	0.002 (3)	0.014 (3)	0.010 (3)
C31	0.048 (4)	0.037 (4)	0.027 (3)	0.013 (3)	−0.005 (3)	0.000 (3)
C32	0.060 (5)	0.061 (5)	0.028 (4)	0.019 (4)	−0.009 (4)	0.001 (4)
C33	0.061 (5)	0.042 (4)	0.030 (3)	0.004 (4)	−0.001 (3)	0.015 (3)
C34	0.046 (4)	0.055 (4)	0.044 (4)	0.009 (4)	0.003 (3)	−0.008 (4)
C35	0.042 (4)	0.045 (4)	0.039 (4)	0.000 (3)	−0.001 (4)	0.007 (3)
C36	0.047 (4)	0.068 (5)	0.046 (4)	0.008 (4)	0.022 (3)	0.007 (4)
C37	0.027 (4)	0.080 (6)	0.081 (6)	−0.013 (4)	0.010 (4)	0.008 (5)
C38	0.073 (6)	0.049 (4)	0.058 (5)	−0.019 (4)	0.004 (5)	0.009 (4)
C39	0.060 (5)	0.039 (4)	0.027 (3)	−0.006 (4)	0.005 (3)	0.008 (3)
C40	0.037 (4)	0.054 (4)	0.044 (4)	0.006 (4)	0.010 (3)	0.004 (4)
C41	0.102 (7)	0.032 (4)	0.052 (5)	0.015 (4)	0.014 (5)	0.005 (4)
C42	0.072 (5)	0.037 (4)	0.041 (4)	−0.003 (4)	0.018 (4)	−0.004 (3)
C43	0.096 (6)	0.041 (4)	0.065 (5)	0.006 (4)	0.048 (4)	−0.008 (4)
C44	0.105 (7)	0.032 (4)	0.079 (5)	0.012 (4)	0.043 (5)	−0.007 (4)

Geometric parameters (Å, º)

Co1—O7^i	1.993 (5)	C11—H11	0.9300
Co1—N1	1.998 (6)	C12—C13	1.397 (10)
Co1—O1	2.016 (5)	C12—H12	0.9300
Co1—N4^ii	2.066 (7)	C13—C14	1.385 (10)
Co1—O2	2.397 (6)	C13—C16	1.490 (10)
Co2—O6^iii	1.956 (5)	C14—H14	0.9300
Co2—O3	2.003 (5)	C17—H17	0.9300
Co2—N5	2.008 (7)	C18—C19	1.331 (11)
Co2—N8^iv	2.044 (6)	C18—H18	0.9300
O1—C7	1.247 (7)	C19—H19	0.9300
O2—C7	1.225 (7)	C20—C21	1.492 (14)
O3—C8	1.292 (7)	C20—H20A	0.9700
O4—C8	1.231 (6)	C20—H20B	0.9700
O5—C15	1.236 (7)	C21—C22	1.345 (14)
O6—C15	1.286 (7)	C21—C26	1.356 (12)
O7—C16	1.252 (10)	C22—C23	1.394 (15)
O8—C16	1.225 (10)	C22—H22	0.9300
N1—C17	1.329 (9)	C23—C24	1.343 (14)
N1—C18	1.332 (10)	C23—H23	0.9300
N2—C17	1.323 (9)	C24—C25	1.388 (14)
N2—C19	1.324 (10)	C24—H24	0.9300
N2—C20	1.471 (10)	C25—C26	1.413 (13)
N3—C30	1.328 (12)	C25—C27	1.520 (13)
N3—C28	1.356 (11)	C26—H26	0.9300
N3—C27	1.454 (11)	C27—H27A	0.9700
N4—C28	1.262 (11)	C27—H27B	0.9700
N4—C29	1.410 (12)	C28—H28	0.9300
N5—C31	1.310 (10)	C29—C30	1.370 (13)
N5—C33	1.390 (9)	C29—H29	0.9300
N6—C31	1.337 (9)	C30—H30	0.9300
N6—C32	1.389 (9)	C31—H31	0.9300
N6—C34	1.452 (10)	C32—C33	1.317 (11)
N7—C42	1.342 (9)	C32—H32	0.9300
N7—C44	1.349 (10)	C33—H33	0.9300
N7—C41	1.461 (10)	C34—C35	1.499 (10)
N8—C42	1.283 (9)	C34—H34A	0.9700
N8—C43	1.370 (9)	C34—H34B	0.9700
C1—C2	1.387 (7)	C35—C36	1.356 (10)
C1—C6	1.397 (9)	C35—C40	1.408 (10)
C1—C9	1.518 (9)	C36—C37	1.432 (12)
C2—C3	1.403 (9)	C36—H36	0.9300
C2—C7	1.492 (3)	C37—C38	1.341 (12)
C3—C4	1.401 (11)	C37—H37	0.9300
C3—H3	0.9300	C38—C39	1.361 (12)
C4—C5	1.352 (8)	C38—H38	0.9300
C4—H4	0.9300	C39—C40	1.386 (10)
C5—C6	1.423 (8)	C39—C41	1.505 (11)
C5—C8	1.492 (3)	C40—H40	0.9300
C6—H6	0.9300	C41—H41A	0.9700
C9—C14	1.389 (9)	C41—H41B	0.9700
C9—C10	1.409 (8)	C42—H42	0.9300
C10—C11	1.388 (9)	C43—C44	1.358 (12)
C10—C15	1.492 (3)	C43—H43	0.9300
C11—C12	1.383 (9)	C44—H44	0.9300
O7^i—Co1—N1	114.0 (2)	N1—C17—H17	123.8
O7^i—Co1—O1	125.8 (2)	C19—C18—N1	112.3 (7)
N1—Co1—O1	106.9 (2)	C19—C18—H18	123.9
O7^i—Co1—N4^ii	108.0 (3)	N1—C18—H18	123.9
N1—Co1—N4^ii	104.4 (3)	N2—C19—C18	106.1 (7)
O1—Co1—N4^ii	94.3 (3)	N2—C19—H19	126.9
O7^i—Co1—O2	90.2 (2)	C18—C19—H19	126.9
N1—Co1—O2	86.8 (2)	N2—C20—C21	112.0 (7)
O1—Co1—O2	57.5 (2)	N2—C20—H20A	109.2
N4^ii—Co1—O2	151.8 (2)	C21—C20—H20A	109.2
O6^iii—Co2—O3	117.1 (2)	N2—C20—H20B	109.2
O6^iii—Co2—N5	107.9 (2)	C21—C20—H20B	109.2
O3—Co2—N5	99.5 (2)	H20A—C20—H20B	107.9
O6^iii—Co2—N8^iv	116.4 (2)	C22—C21—C26	117.6 (10)
O3—Co2—N8^iv	106.4 (2)	C22—C21—C20	122.0 (9)
N5—Co2—N8^iv	108.0 (2)	C26—C21—C20	119.9 (9)
C7—O1—Co1	99.2 (3)	C21—C22—C23	121.5 (10)
C7—O2—Co1	82.0 (4)	C21—C22—H22	119.3
C8—O3—Co2	113.8 (3)	C23—C22—H22	119.3
C15—O6—Co2^v	114.6 (4)	C24—C23—C22	119.9 (10)
C16—O7—Co1^ii	113.1 (5)	C24—C23—H23	120.1
C17—N1—C18	102.5 (6)	C22—C23—H23	120.1
C17—N1—Co1	123.8 (5)	C23—C24—C25	121.0 (10)
C18—N1—Co1	133.3 (5)	C23—C24—H24	119.5
C17—N2—C19	106.7 (6)	C25—C24—H24	119.5
C17—N2—C20	126.0 (7)	C24—C25—C26	116.2 (9)
C19—N2—C20	127.2 (7)	C24—C25—C27	122.7 (9)
C30—N3—C28	108.7 (8)	C26—C25—C27	120.3 (9)
C30—N3—C27	124.2 (8)	C21—C26—C25	123.2 (9)
C28—N3—C27	127.0 (8)	C21—C26—H26	118.4
C28—N4—C29	105.9 (8)	C25—C26—H26	118.4
C28—N4—Co1^i	126.1 (6)	N3—C27—C25	111.3 (8)
C29—N4—Co1^i	127.7 (6)	N3—C27—H27A	109.4
C31—N5—C33	103.8 (6)	C25—C27—H27A	109.4
C31—N5—Co2	129.7 (5)	N3—C27—H27B	109.4
C33—N5—Co2	126.3 (5)	C25—C27—H27B	109.4
C31—N6—C32	105.4 (6)	H27A—C27—H27B	108.0
C31—N6—C34	127.8 (6)	N4—C28—N3	111.6 (8)
C32—N6—C34	126.5 (6)	N4—C28—H28	124.2
C42—N7—C44	106.5 (6)	N3—C28—H28	124.2
C42—N7—C41	128.4 (6)	C30—C29—N4	108.0 (8)
C44—N7—C41	125.0 (6)	C30—C29—H29	126.0
C42—N8—C43	107.3 (6)	N4—C29—H29	126.0
C42—N8—Co2^vi	127.3 (5)	N3—C30—C29	105.7 (9)
C43—N8—Co2^vi	125.0 (5)	N3—C30—H30	127.1
C2—C1—C6	120.5 (6)	C29—C30—H30	127.1
C2—C1—C9	122.1 (5)	N5—C31—N6	113.3 (6)
C6—C1—C9	117.4 (5)	N5—C31—H31	123.4
C1—C2—C3	117.0 (5)	N6—C31—H31	123.4
C1—C2—C7	126.8 (5)	C33—C32—N6	106.9 (6)
C3—C2—C7	116.1 (5)	C33—C32—H32	126.6
C4—C3—C2	122.1 (6)	N6—C32—H32	126.6
C4—C3—H3	118.9	C32—C33—N5	110.6 (7)
C2—C3—H3	118.9	C32—C33—H33	124.7
C5—C4—C3	120.8 (6)	N5—C33—H33	124.7
C5—C4—H4	119.6	N6—C34—C35	115.3 (6)
C3—C4—H4	119.6	N6—C34—H34A	108.4
C4—C5—C6	118.1 (5)	C35—C34—H34A	108.4
C4—C5—C8	122.1 (5)	N6—C34—H34B	108.4
C6—C5—C8	119.8 (4)	C35—C34—H34B	108.4
C1—C6—C5	121.0 (5)	H34A—C34—H34B	107.5
C1—C6—H6	119.5	C36—C35—C40	118.3 (7)
C5—C6—H6	119.5	C36—C35—C34	120.9 (7)
O2—C7—O1	120.8 (4)	C40—C35—C34	120.8 (7)
O2—C7—C2	119.0 (5)	C35—C36—C37	119.9 (7)
O1—C7—C2	120.1 (4)	C35—C36—H36	120.1
O4—C8—O3	121.8 (4)	C37—C36—H36	120.1
O4—C8—C5	121.7 (4)	C38—C37—C36	120.0 (7)
O3—C8—C5	116.4 (4)	C38—C37—H37	120.0
C14—C9—C10	119.4 (6)	C36—C37—H37	120.0
C14—C9—C1	118.7 (6)	C37—C38—C39	121.3 (8)
C10—C9—C1	121.9 (5)	C37—C38—H38	119.4
C11—C10—C9	118.5 (4)	C39—C38—H38	119.4
C11—C10—C15	116.9 (5)	C38—C39—C40	119.2 (7)
C9—C10—C15	124.6 (5)	C38—C39—C41	121.7 (7)
C12—C11—C10	121.1 (6)	C40—C39—C41	118.9 (7)
C12—C11—H11	119.4	C39—C40—C35	121.1 (7)
C10—C11—H11	119.4	C39—C40—H40	119.5
C11—C12—C13	120.6 (7)	C35—C40—H40	119.5
C11—C12—H12	119.7	N7—C41—C39	109.1 (6)
C13—C12—H12	119.7	N7—C41—H41A	109.9
C14—C13—C12	118.2 (6)	C39—C41—H41A	109.9
C14—C13—C16	123.2 (7)	N7—C41—H41B	109.9
C12—C13—C16	118.3 (6)	C39—C41—H41B	109.9
C13—C14—C9	121.7 (6)	H41A—C41—H41B	108.3
C13—C14—H14	119.2	N8—C42—N7	111.5 (7)
C9—C14—H14	119.2	N8—C42—H42	124.3
O5—C15—O6	123.8 (4)	N7—C42—H42	124.3
O5—C15—C10	119.8 (5)	C44—C43—N8	107.3 (7)
O6—C15—C10	116.3 (5)	C44—C43—H43	126.4
O8—C16—O7	123.1 (7)	N8—C43—H43	126.4
O8—C16—C13	117.7 (8)	N7—C44—C43	107.5 (7)
O7—C16—C13	119.1 (7)	N7—C44—H44	126.3
N2—C17—N1	112.3 (7)	C43—C44—H44	126.3
N2—C17—H17	123.8
C6—C1—C2—C3	−6.9 (9)	N1—C18—C19—N2	−1.1 (11)
C9—C1—C2—C3	174.6 (6)	C17—N2—C20—C21	25.2 (13)
C6—C1—C2—C7	173.8 (5)	C19—N2—C20—C21	−151.2 (9)
C9—C1—C2—C7	−4.6 (9)	N2—C20—C21—C22	95.4 (11)
C1—C2—C3—C4	3.5 (10)	N2—C20—C21—C26	−76.7 (11)
C7—C2—C3—C4	−177.1 (6)	C26—C21—C22—C23	−7.4 (15)
C2—C3—C4—C5	−0.1 (12)	C20—C21—C22—C23	−179.7 (9)
C3—C4—C5—C6	−0.1 (10)	C21—C22—C23—C24	9.7 (16)
C3—C4—C5—C8	177.3 (6)	C22—C23—C24—C25	−4.6 (16)
C2—C1—C6—C5	7.1 (9)	C23—C24—C25—C26	−2.0 (15)
C9—C1—C6—C5	−174.4 (5)	C23—C24—C25—C27	167.4 (10)
C4—C5—C6—C1	−3.4 (9)	C22—C21—C26—C25	0.4 (14)
C8—C5—C6—C1	179.2 (5)	C20—C21—C26—C25	172.9 (9)
Co1—O2—C7—O1	6.3 (6)	C24—C25—C26—C21	4.3 (15)
Co1—O2—C7—C2	−177.2 (4)	C27—C25—C26—C21	−165.4 (9)
Co1—O1—C7—O2	−7.5 (7)	C30—N3—C27—C25	−47.8 (12)
Co1—O1—C7—C2	176.0 (4)	C28—N3—C27—C25	135.5 (9)
C1—C2—C7—O2	169.0 (6)	C24—C25—C27—N3	139.5 (10)
C3—C2—C7—O2	−10.3 (8)	C26—C25—C27—N3	−51.5 (12)
C1—C2—C7—O1	−14.4 (8)	C29—N4—C28—N3	−2.4 (9)
C3—C2—C7—O1	166.3 (6)	Co1^i—N4—C28—N3	−177.5 (5)
Co2—O3—C8—O4	9.3 (8)	C30—N3—C28—N4	1.4 (10)
Co2—O3—C8—C5	−173.4 (3)	C27—N3—C28—N4	178.5 (8)
C4—C5—C8—O4	−175.7 (6)	C28—N4—C29—C30	2.6 (10)
C6—C5—C8—O4	1.6 (8)	Co1^i—N4—C29—C30	177.6 (6)
C4—C5—C8—O3	7.1 (8)	C28—N3—C30—C29	0.4 (10)
C6—C5—C8—O3	−175.7 (5)	C27—N3—C30—C29	−176.8 (8)
C2—C1—C9—C14	101.9 (7)	N4—C29—C30—N3	−1.8 (10)
C6—C1—C9—C14	−76.6 (8)	C33—N5—C31—N6	0.9 (8)
C2—C1—C9—C10	−77.1 (8)	Co2—N5—C31—N6	−175.7 (5)
C6—C1—C9—C10	104.4 (7)	C32—N6—C31—N5	0.2 (8)
C14—C9—C10—C11	−6.3 (8)	C34—N6—C31—N5	−174.0 (7)
C1—C9—C10—C11	172.6 (6)	C31—N6—C32—C33	−1.3 (8)
C14—C9—C10—C15	172.5 (5)	C34—N6—C32—C33	173.0 (7)
C1—C9—C10—C15	−8.5 (8)	N6—C32—C33—N5	2.0 (9)
C9—C10—C11—C12	2.3 (9)	C31—N5—C33—C32	−1.8 (8)
C15—C10—C11—C12	−176.6 (6)	Co2—N5—C33—C32	175.0 (5)
C10—C11—C12—C13	3.3 (10)	C31—N6—C34—C35	−123.9 (8)
C11—C12—C13—C14	−4.7 (10)	C32—N6—C34—C35	63.0 (10)
C11—C12—C13—C16	−179.7 (7)	N6—C34—C35—C36	−148.0 (7)
C12—C13—C14—C9	0.5 (10)	N6—C34—C35—C40	32.0 (10)
C16—C13—C14—C9	175.3 (7)	C40—C35—C36—C37	−0.9 (11)
C10—C9—C14—C13	5.0 (10)	C34—C35—C36—C37	179.1 (7)
C1—C9—C14—C13	−174.0 (6)	C35—C36—C37—C38	1.6 (12)
Co2^v—O6—C15—O5	2.5 (7)	C36—C37—C38—C39	−4.1 (13)
Co2^v—O6—C15—C10	179.1 (3)	C37—C38—C39—C40	6.0 (12)
C11—C10—C15—O5	145.6 (6)	C37—C38—C39—C41	−177.9 (8)
C9—C10—C15—O5	−33.3 (7)	C38—C39—C40—C35	−5.3 (11)
C11—C10—C15—O6	−31.2 (7)	C41—C39—C40—C35	178.5 (7)
C9—C10—C15—O6	150.0 (5)	C36—C35—C40—C39	2.8 (11)
Co1^ii—O7—C16—O8	−4.3 (10)	C34—C35—C40—C39	−177.2 (7)
Co1^ii—O7—C16—C13	172.2 (5)	C42—N7—C41—C39	30.6 (12)
C14—C13—C16—O8	−144.2 (8)	C44—N7—C41—C39	−154.2 (8)
C12—C13—C16—O8	30.6 (10)	C38—C39—C41—N7	87.5 (9)
C14—C13—C16—O7	39.1 (11)	C40—C39—C41—N7	−96.4 (8)
C12—C13—C16—O7	−146.1 (7)	C43—N8—C42—N7	−1.5 (9)
C19—N2—C17—N1	−3.6 (10)	Co2^vi—N8—C42—N7	171.8 (5)
C20—N2—C17—N1	179.5 (8)	C44—N7—C42—N8	0.4 (10)
C18—N1—C17—N2	2.8 (9)	C41—N7—C42—N8	176.3 (7)
Co1—N1—C17—N2	175.8 (5)	C42—N8—C43—C44	2.1 (10)
C17—N1—C18—C19	−1.0 (10)	Co2^vi—N8—C43—C44	−171.4 (6)
Co1—N1—C18—C19	−173.0 (6)	C42—N7—C44—C43	0.9 (10)
C17—N2—C19—C18	2.7 (10)	C41—N7—C44—C43	−175.2 (8)
C20—N2—C19—C18	179.7 (9)	N8—C43—C44—N7	−1.8 (10)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C42—H42···O5^vii	0.93	2.54	3.223 (9)	131
C34—H34A···O4^vii	0.97	2.40	3.329 (10)	161
C31—H31···O5^iii	0.93	2.35	3.044 (8)	131
C29—H29···O8^viii	0.93	2.28	2.916 (11)	125
C20—H20A···O4^ix	0.97	2.38	3.132 (10)	133
C17—H17···O8^i	0.93	2.26	2.965 (9)	132

Symmetry codes: (i) x−1/2, −y+2, z−1/2; (iii) x−1/2, −y+1, z+1/2; (vii) x−1, y, z; (viii) x−1, y, z−1; (ix) x, y, z−1.

Poly[[aqua(µ₄-biphenyl-2,2',5,5'-tetracarboxylato){1,4-bis[(1H-imidazol-1-yl)methyl]benzene}dicobalt(II)] dihydrate] (sf180611a_sq)

Crystal data

[Co2(C16H6O8)(C14H14N4)2(H2O)2]·4H2O	F(000) = 2048
Mr = 1028.18	Dx = 1.491 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.263 (4) Å	Cell parameters from 6902 reflections
b = 12.366 (2) Å	θ = 3.3–22.3°
c = 19.608 (4) Å	µ = 0.82 mm^−1
β = 120.91 (3)°	T = 200 K
V = 4423.5 (19) Å^3	Block, pink
Z = 4	0.36 × 0.35 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer	4104 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.039
φ and ω scans	θmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −26→26
Tmin = 0.751, Tmax = 0.781	k = 0→15
8382 measured reflections	l = −23→24
4563 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 9.6701P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.003
4563 reflections	Δρmax = 0.78 e Å^−3
298 parameters	Δρmin = −0.80 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Co1	0.07286 (2)	0.70505 (2)	−0.01446 (2)	0.01321 (11)
O1	0.07928 (8)	0.65436 (13)	0.08867 (9)	0.0170 (3)
O2	0.19863 (9)	0.66658 (16)	0.18208 (10)	0.0273 (4)
O3	0.09524 (9)	0.44032 (13)	0.43989 (9)	0.0188 (3)
O4	0.07115 (10)	0.29009 (13)	0.37121 (10)	0.0230 (4)
O5	0.19253 (9)	0.72765 (14)	0.05045 (10)	0.0220 (3)
H5A	0.207813	0.718958	0.097910	0.033*
H5B	0.212262	0.681228	0.037880	0.033*
N1	−0.04074 (10)	0.68173 (15)	−0.07571 (11)	0.0150 (4)
N2	−0.15208 (10)	0.64318 (15)	−0.10064 (11)	0.0170 (4)
N3	0.07227 (10)	0.87336 (16)	−0.00624 (11)	0.0183 (4)
N4	0.06418 (11)	1.04669 (15)	−0.03789 (11)	0.0182 (4)
C1	0.13438 (12)	0.63412 (17)	0.15710 (12)	0.0157 (4)
C2	0.12033 (12)	0.56710 (17)	0.21236 (12)	0.0147 (4)
C3	0.05031 (12)	0.56074 (17)	0.20151 (12)	0.0151 (4)
H3	0.010583	0.595415	0.156960	0.018*
C4	0.03742 (11)	0.50431 (17)	0.25493 (12)	0.0143 (4)
C5	0.09616 (12)	0.44929 (17)	0.31855 (12)	0.0149 (4)
C6	0.16583 (12)	0.45135 (18)	0.32742 (13)	0.0182 (4)
H6	0.204821	0.411527	0.369159	0.022*
C7	0.17826 (12)	0.51114 (18)	0.27566 (12)	0.0172 (4)
H7	0.226035	0.514202	0.283080	0.021*
C8	0.08633 (11)	0.38978 (18)	0.37979 (12)	0.0154 (4)
C9	−0.09155 (13)	0.72698 (19)	−0.14821 (13)	0.0189 (4)
H9A	−0.080094	0.767527	−0.181573	0.023*
C10	−0.16073 (13)	0.70409 (17)	−0.16412 (13)	0.0190 (5)
H10	−0.205641	0.725634	−0.209554	0.023*
C11	−0.07934 (12)	0.63170 (17)	−0.04935 (13)	0.0158 (4)
H11	−0.058550	0.592833	−0.000722	0.019*
C12	−0.21106 (12)	0.60198 (18)	−0.08929 (14)	0.0202 (5)
H12A	−0.195519	0.532184	−0.060573	0.024*
H12B	−0.255226	0.588397	−0.141950	0.024*
C13	−0.23058 (12)	0.67977 (19)	−0.04305 (14)	0.0178 (4)
C14	−0.21887 (16)	0.6508 (2)	0.03073 (16)	0.0295 (6)
H14	−0.197321	0.582681	0.052715	0.035*
C15	−0.26200 (17)	0.7806 (2)	−0.07340 (17)	0.0307 (6)
H15	−0.270436	0.802611	−0.123842	0.037*
C16	0.11350 (13)	0.93326 (19)	0.06213 (14)	0.0212 (5)
H16	0.141083	0.904260	0.114292	0.025*
C17	0.10863 (14)	1.0403 (2)	0.04344 (14)	0.0236 (5)
H17	0.131363	1.098723	0.079354	0.028*
C18	0.04301 (13)	0.94502 (18)	−0.06531 (14)	0.0199 (5)
H18	0.011356	0.926958	−0.119684	0.024*
C19	0.04167 (15)	1.14914 (18)	−0.08338 (15)	0.0246 (5)
H19A	0.082715	1.201271	−0.057358	0.030*
H19B	−0.000201	1.179807	−0.081059	0.030*
C20	0.01982 (13)	1.13774 (17)	−0.16960 (14)	0.0193 (4)
C21	−0.05236 (16)	1.1383 (3)	−0.22953 (18)	0.0462 (9)
H21	−0.089691	1.139251	−0.216549	0.055*
C22	0.07179 (15)	1.1375 (4)	−0.19113 (18)	0.0487 (9)
H22	0.122204	1.136768	−0.150922	0.058*
O6	0.20598 (12)	0.10026 (17)	0.45806 (14)	0.0406 (5)
H6A	0.198539	0.149349	0.481129	0.061*
H6B	0.169008	0.094237	0.413919	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.01959 (18)	0.01124 (17)	0.01141 (17)	0.00095 (10)	0.00984 (13)	0.00077 (9)
O1	0.0197 (7)	0.0204 (8)	0.0126 (7)	0.0015 (6)	0.0095 (6)	0.0042 (6)
O2	0.0230 (8)	0.0360 (10)	0.0189 (8)	−0.0085 (7)	0.0078 (7)	0.0059 (7)
O3	0.0280 (8)	0.0183 (8)	0.0133 (7)	−0.0018 (6)	0.0128 (6)	−0.0002 (6)
O4	0.0389 (10)	0.0167 (8)	0.0219 (8)	−0.0043 (6)	0.0217 (8)	−0.0024 (6)
O5	0.0221 (8)	0.0264 (8)	0.0216 (8)	−0.0021 (7)	0.0141 (7)	−0.0016 (7)
N1	0.0207 (9)	0.0140 (8)	0.0112 (8)	0.0022 (7)	0.0089 (7)	−0.0010 (7)
N2	0.0197 (9)	0.0163 (9)	0.0158 (9)	0.0015 (7)	0.0097 (7)	−0.0013 (7)
N3	0.0236 (10)	0.0153 (9)	0.0170 (9)	−0.0024 (7)	0.0112 (8)	−0.0028 (7)
N4	0.0273 (10)	0.0132 (9)	0.0183 (9)	−0.0022 (7)	0.0146 (8)	−0.0038 (7)
C1	0.0207 (10)	0.0158 (10)	0.0109 (9)	−0.0010 (8)	0.0084 (8)	−0.0009 (8)
C2	0.0224 (10)	0.0121 (9)	0.0106 (9)	−0.0013 (8)	0.0092 (8)	−0.0020 (7)
C3	0.0203 (10)	0.0137 (10)	0.0093 (9)	0.0008 (8)	0.0061 (8)	−0.0003 (7)
C4	0.0198 (11)	0.0141 (10)	0.0099 (9)	−0.0020 (8)	0.0082 (8)	−0.0028 (7)
C5	0.0245 (10)	0.0128 (9)	0.0103 (9)	0.0000 (8)	0.0111 (8)	−0.0004 (7)
C6	0.0205 (10)	0.0195 (10)	0.0131 (10)	0.0033 (8)	0.0075 (8)	0.0021 (8)
C7	0.0194 (10)	0.0196 (11)	0.0135 (10)	0.0008 (8)	0.0091 (8)	−0.0001 (8)
C8	0.0170 (10)	0.0176 (10)	0.0112 (9)	0.0028 (8)	0.0070 (8)	0.0030 (8)
C9	0.0267 (11)	0.0180 (10)	0.0119 (10)	0.0026 (9)	0.0098 (9)	0.0013 (8)
C10	0.0224 (11)	0.0183 (11)	0.0126 (10)	0.0032 (8)	0.0063 (9)	0.0000 (8)
C11	0.0219 (10)	0.0135 (9)	0.0136 (9)	0.0010 (8)	0.0102 (8)	−0.0014 (8)
C12	0.0188 (10)	0.0172 (10)	0.0245 (11)	−0.0021 (8)	0.0112 (9)	−0.0030 (9)
C13	0.0167 (10)	0.0160 (10)	0.0227 (11)	−0.0004 (8)	0.0115 (9)	−0.0001 (9)
C14	0.0448 (15)	0.0199 (11)	0.0281 (13)	0.0142 (11)	0.0219 (12)	0.0091 (10)
C15	0.0485 (16)	0.0247 (13)	0.0257 (13)	0.0118 (11)	0.0239 (12)	0.0086 (10)
C16	0.0287 (12)	0.0226 (11)	0.0146 (10)	−0.0029 (9)	0.0129 (9)	−0.0038 (9)
C17	0.0326 (13)	0.0197 (11)	0.0198 (11)	−0.0063 (9)	0.0145 (10)	−0.0083 (9)
C18	0.0288 (12)	0.0130 (10)	0.0169 (10)	−0.0021 (8)	0.0111 (9)	−0.0022 (8)
C19	0.0393 (14)	0.0122 (10)	0.0253 (12)	−0.0005 (9)	0.0186 (11)	−0.0019 (9)
C20	0.0291 (12)	0.0097 (9)	0.0237 (11)	−0.0016 (8)	0.0168 (10)	−0.0008 (8)
C21	0.0265 (14)	0.089 (3)	0.0314 (15)	0.0045 (15)	0.0209 (12)	0.0041 (16)
C22	0.0196 (12)	0.100 (3)	0.0257 (14)	−0.0080 (15)	0.0112 (11)	−0.0090 (16)
O6	0.0497 (12)	0.0363 (11)	0.0528 (13)	−0.0044 (9)	0.0385 (11)	−0.0086 (10)

Geometric parameters (Å, º)

Co1—O1	2.0536 (15)	C5—C8	1.512 (3)
Co1—N3	2.088 (2)	C6—C7	1.386 (3)
Co1—N1	2.093 (2)	C6—H6	0.9500
Co1—O3^i	2.1672 (16)	C7—H7	0.9500
Co1—O5	2.2013 (18)	C9—C10	1.367 (3)
Co1—O4^i	2.2240 (18)	C9—H9A	0.9500
O1—C1	1.273 (3)	C10—H10	0.9500
O2—C1	1.257 (3)	C11—H11	0.9500
O3—C8	1.259 (3)	C12—C13	1.519 (3)
O4—C8	1.263 (3)	C12—H12A	0.9900
O5—H5A	0.8200	C12—H12B	0.9900
O5—H5B	0.8200	C13—C14	1.383 (3)
N1—C11	1.326 (3)	C13—C15	1.395 (3)
N1—C9	1.387 (3)	C14—C15^iii	1.391 (4)
N2—C11	1.351 (3)	C14—H14	0.9500
N2—C10	1.384 (3)	C15—H15	0.9500
N2—C12	1.473 (3)	C16—C17	1.363 (3)
N3—C18	1.332 (3)	C16—H16	0.9500
N3—C16	1.381 (3)	C17—H17	0.9500
N4—C18	1.350 (3)	C18—H18	0.9500
N4—C17	1.376 (3)	C19—C20	1.512 (3)
N4—C19	1.480 (3)	C19—H19A	0.9900
C1—C2	1.511 (3)	C19—H19B	0.9900
C2—C3	1.394 (3)	C20—C22	1.371 (4)
C2—C7	1.402 (3)	C20—C21	1.373 (4)
C3—C4	1.398 (3)	C21—C22^iv	1.389 (4)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.407 (3)	C22—H22	0.9500
C4—C4^ii	1.501 (4)	O6—H6A	0.8196
C5—C6	1.400 (3)	O6—H6B	0.8207
O1—Co1—N3	103.19 (7)	C2—C7—H7	120.0
O1—Co1—N1	89.78 (7)	O3—C8—O4	120.9 (2)
N3—Co1—N1	97.51 (7)	O3—C8—C5	119.08 (19)
O1—Co1—O3^i	103.64 (6)	O4—C8—C5	119.96 (19)
N3—Co1—O3^i	150.46 (7)	C10—C9—N1	109.3 (2)
N1—Co1—O3^i	94.72 (7)	C10—C9—H9A	125.3
O1—Co1—O5	89.83 (7)	N1—C9—H9A	125.3
N3—Co1—O5	83.10 (7)	C9—C10—N2	106.1 (2)
N1—Co1—O5	179.34 (7)	C9—C10—H10	127.0
O3^i—Co1—O5	84.85 (6)	N2—C10—H10	127.0
O1—Co1—O4^i	163.57 (6)	N1—C11—N2	111.20 (19)
N3—Co1—O4^i	93.05 (7)	N1—C11—H11	124.4
N1—Co1—O4^i	90.51 (8)	N2—C11—H11	124.4
O3^i—Co1—O4^i	59.97 (6)	N2—C12—C13	112.73 (18)
O5—Co1—O4^i	89.71 (7)	N2—C12—H12A	109.0
C1—O1—Co1	131.11 (14)	C13—C12—H12A	109.0
C8—O3—Co1^v	90.88 (13)	N2—C12—H12B	109.0
C8—O4—Co1^v	88.21 (13)	C13—C12—H12B	109.0
Co1—O5—H5A	107.8	H12A—C12—H12B	107.8
Co1—O5—H5B	110.8	C14—C13—C15	117.8 (2)
H5A—O5—H5B	106.5	C14—C13—C12	120.2 (2)
C11—N1—C9	105.99 (19)	C15—C13—C12	121.9 (2)
C11—N1—Co1	127.12 (15)	C13—C14—C15^iii	121.3 (2)
C9—N1—Co1	126.46 (16)	C13—C14—H14	119.3
C11—N2—C10	107.41 (19)	C15^iii—C14—H14	119.3
C11—N2—C12	126.09 (19)	C14^iii—C15—C13	120.8 (2)
C10—N2—C12	126.46 (19)	C14^iii—C15—H15	119.6
C18—N3—C16	105.51 (19)	C13—C15—H15	119.6
C18—N3—Co1	127.93 (15)	C17—C16—N3	109.7 (2)
C16—N3—Co1	125.71 (16)	C17—C16—H16	125.1
C18—N4—C17	107.31 (19)	N3—C16—H16	125.1
C18—N4—C19	128.20 (19)	C16—C17—N4	106.2 (2)
C17—N4—C19	124.38 (19)	C16—C17—H17	126.9
O2—C1—O1	125.1 (2)	N4—C17—H17	126.9
O2—C1—C2	118.13 (19)	N3—C18—N4	111.2 (2)
O1—C1—C2	116.73 (19)	N3—C18—H18	124.4
C3—C2—C7	119.4 (2)	N4—C18—H18	124.4
C3—C2—C1	120.71 (19)	N4—C19—C20	114.36 (18)
C7—C2—C1	119.9 (2)	N4—C19—H19A	108.7
C2—C3—C4	121.3 (2)	C20—C19—H19A	108.7
C2—C3—H3	119.4	N4—C19—H19B	108.7
C4—C3—H3	119.4	C20—C19—H19B	108.7
C3—C4—C5	118.64 (19)	H19A—C19—H19B	107.6
C3—C4—C4^ii	120.4 (2)	C22—C20—C21	117.4 (2)
C5—C4—C4^ii	120.9 (2)	C22—C20—C19	120.8 (2)
C6—C5—C4	120.15 (19)	C21—C20—C19	121.5 (2)
C6—C5—C8	118.64 (19)	C20—C21—C22^iv	121.1 (3)
C4—C5—C8	121.19 (19)	C20—C21—H21	119.4
C7—C6—C5	120.4 (2)	C22^iv—C21—H21	119.4
C7—C6—H6	119.8	C20—C22—C21^iv	121.5 (3)
C5—C6—H6	119.8	C20—C22—H22	119.3
C6—C7—C2	120.0 (2)	C21^iv—C22—H22	119.3
C6—C7—H7	120.0	H6A—O6—H6B	107.3
Co1—O1—C1—O2	18.8 (3)	C12—N2—C10—C9	177.9 (2)
Co1—O1—C1—C2	−162.08 (14)	C9—N1—C11—N2	−0.5 (2)
O2—C1—C2—C3	157.1 (2)	Co1—N1—C11—N2	172.36 (14)
O1—C1—C2—C3	−22.0 (3)	C10—N2—C11—N1	0.3 (2)
O2—C1—C2—C7	−22.4 (3)	C12—N2—C11—N1	−177.54 (19)
O1—C1—C2—C7	158.5 (2)	C11—N2—C12—C13	86.5 (3)
C7—C2—C3—C4	3.4 (3)	C10—N2—C12—C13	−90.9 (3)
C1—C2—C3—C4	−176.14 (19)	N2—C12—C13—C14	−115.5 (3)
C2—C3—C4—C5	−2.9 (3)	N2—C12—C13—C15	65.9 (3)
C2—C3—C4—C4^ii	176.11 (17)	C15—C13—C14—C15^iii	0.3 (5)
C3—C4—C5—C6	−0.2 (3)	C12—C13—C14—C15^iii	−178.3 (2)
C4^ii—C4—C5—C6	−179.16 (17)	C14—C13—C15—C14^iii	−0.3 (5)
C3—C4—C5—C8	178.04 (19)	C12—C13—C15—C14^iii	178.3 (2)
C4^ii—C4—C5—C8	−0.9 (3)	C18—N3—C16—C17	0.0 (3)
C4—C5—C6—C7	2.7 (3)	Co1—N3—C16—C17	170.05 (17)
C8—C5—C6—C7	−175.6 (2)	N3—C16—C17—N4	−0.5 (3)
C5—C6—C7—C2	−2.1 (3)	C18—N4—C17—C16	0.9 (3)
C3—C2—C7—C6	−0.9 (3)	C19—N4—C17—C16	177.4 (2)
C1—C2—C7—C6	178.69 (19)	C16—N3—C18—N4	0.6 (3)
Co1^v—O3—C8—O4	−0.7 (2)	Co1—N3—C18—N4	−169.19 (15)
Co1^v—O3—C8—C5	−178.99 (17)	C17—N4—C18—N3	−0.9 (3)
Co1^v—O4—C8—O3	0.7 (2)	C19—N4—C18—N3	−177.3 (2)
Co1^v—O4—C8—C5	178.95 (18)	C18—N4—C19—C20	−27.5 (3)
C6—C5—C8—O3	90.1 (3)	C17—N4—C19—C20	156.7 (2)
C4—C5—C8—O3	−88.2 (3)	N4—C19—C20—C22	−83.4 (3)
C6—C5—C8—O4	−88.2 (3)	N4—C19—C20—C21	103.2 (3)
C4—C5—C8—O4	93.5 (3)	C22—C20—C21—C22^iv	0.7 (4)
C11—N1—C9—C10	0.6 (2)	C19—C20—C21—C22^iv	174.2 (3)
Co1—N1—C9—C10	−172.34 (15)	C21—C20—C22—C21^iv	0.3 (5)
N1—C9—C10—N2	−0.5 (2)	C19—C20—C22—C21^iv	−173.3 (3)
C11—N2—C10—C9	0.1 (2)

Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x, y, −z+1/2; (iii) −x−1/2, −y+3/2, −z; (iv) −x, y, −z−1/2; (v) x, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2	0.82	1.87	2.628 (2)	152
O5—H5B···O6^vi	0.82	1.97	2.745 (3)	157
C10—H10···O2^vii	0.95	2.45	3.366 (3)	163
C11—H11···O3^ii	0.95	2.56	3.327 (3)	138
C12—H12A···O3^ii	0.99	2.50	3.351 (3)	144
C19—H19B···O1^viii	0.99	2.61	3.500 (3)	150
O6—H6A···O5^v	0.82	2.09	2.903 (3)	173

Symmetry codes: (ii) −x, y, −z+1/2; (v) x, −y+1, z+1/2; (vi) −x+1/2, y+1/2, −z+1/2; (vii) x−1/2, −y+3/2, z−1/2; (viii) −x, −y+2, −z.