Crystal structure of a novel one-dimensional zigzag chain-like cobalt(II) coordination polymer constructed from 4,4′-bi­pyridine and 2-hy­droxy­benzoate ligands

The synthesis, crystal structure and physical properties of a novel one-dimensional zigzag chain-like Co^II coordination polymer, [Co₂(2-OHbenz)₄(4,4′-bpy)_2.5(H₂O)]_n, constructed from 4,4′-bi­pyridine (4,4′-bpy) and 2-hy­droxy­benzoate (2-OHbenz) are reported.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.088
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Co1      --O1       .       11.6 s.u.

Author Response: According to the metal is certainly identified, thus the checkcif alerts of Hirshfeld Test Diff (M-X) Co -- O may be ignored.

PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Co1      --O2       .       10.8 s.u.

Author Response: According to the metal is certainly identified, thus the checkcif alerts of Hirshfeld Test Diff (M-X) Co -- O may be ignored.

PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Co2      --O7       .       13.4 s.u.

Author Response: According to the metal is certainly identified, thus the checkcif alerts of Hirshfeld Test Diff (M-X) Co -- O may be ignored.

PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Co2      --O8       .       10.5 s.u.

Author Response: According to the metal is certainly identified, thus the checkcif alerts of Hirshfeld Test Diff (M-X) Co -- O may be ignored.

PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         15 Note

Author Response: The unit cell is reasonable large and these low angle reflections are probably missing due to the beamstop.

Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        4.1 Ratio
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         O1 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C22 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C23 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C42 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         11 Note
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          6 Report
PLAT794_ALERT_5_G Tentative Bond Valency for Co1       (II)      .       1.82 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Co2       (II)      .       1.80 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          6 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   5 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

catena-Poly[[(4,4'-bipyridine-κN)(µ-2-hydroxybenzoato-κ²O:O')(2-hydroxybenzoato-κ²O,O')cobalt(II)]-µ-4,4'-bipyridine-κ²N:N'-[aquahemi(µ-4,4'-bipyridine-κ²N:N')(2-hydroxybenzoato-κO)(2-hydroxybenzoato-κ²O,O')cobalt(II)]

Crystal data

[Co2(C7H5O3)4(C10H8N2)2.5(H2O)]	Z = 2
Mr = 1074.77	F(000) = 1106
Triclinic, P1	Dx = 1.492 Mg m^−3
a = 10.8832 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4742 (19) Å	Cell parameters from 9918 reflections
c = 19.905 (3) Å	θ = 3.1–28.2°
α = 74.295 (5)°	µ = 0.77 mm^−1
β = 89.791 (5)°	T = 296 K
γ = 88.502 (6)°	Block, red
V = 2392.0 (7) Å^3	0.32 × 0.24 × 0.2 mm

Data collection

Bruker D8 Quest CMOS Photon II diffractometer	9771 independent reflections
Radiation source: sealed x-ray tube, Mo	7780 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 7.39 pixels mm^-1	θmax = 26.4°, θmin = 3.0°
ω and φ scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −14→14
Tmin = 0.677, Tmax = 0.746	l = −24→24
60283 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0419P)^2 + 0.8816P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
9771 reflections	Δρmax = 0.43 e Å^−3
682 parameters	Δρmin = −0.29 e Å^−3
6 restraints

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	0.38320 (2)	0.10363 (2)	0.54244 (2)	0.02725 (7)
Co2	0.06977 (2)	0.72632 (2)	0.02018 (2)	0.03175 (8)
O1	0.40605 (13)	0.25879 (14)	0.58404 (9)	0.0484 (4)
O2	0.23200 (13)	0.16721 (13)	0.59633 (8)	0.0409 (3)
O3	0.4298 (2)	0.4553 (2)	0.61905 (15)	0.0980 (9)
H3	0.443 (4)	0.398 (2)	0.6003 (19)	0.121 (14)*
O4	0.55720 (12)	0.11808 (13)	0.50300 (8)	0.0402 (3)
O5	0.72507 (12)	0.03072 (12)	0.47519 (7)	0.0344 (3)
O6	0.93656 (14)	0.12657 (17)	0.47886 (11)	0.0602 (5)
H8	0.888 (2)	0.077 (2)	0.4705 (14)	0.071 (9)*
O7	−0.11751 (13)	0.67237 (13)	0.06159 (7)	0.0406 (3)
O8	−0.03026 (13)	0.83546 (13)	0.07254 (8)	0.0438 (4)
O9	−0.3306 (2)	0.6158 (2)	0.11428 (13)	0.0875 (7)
H13	−0.2608 (17)	0.610 (3)	0.0971 (18)	0.106 (13)*
O10	−0.00286 (14)	0.81713 (14)	−0.07657 (7)	0.0454 (4)
O11	0.10789 (16)	0.73590 (15)	−0.14789 (8)	0.0543 (4)
O12	0.08458 (17)	0.81806 (18)	−0.27880 (9)	0.0592 (5)
H18	0.107 (3)	0.775 (2)	−0.2386 (9)	0.088 (11)*
O13	0.13809 (16)	0.59112 (14)	−0.02174 (8)	0.0441 (4)
H26	0.135 (3)	0.623 (2)	−0.0648 (6)	0.078 (10)*
H27	0.2003 (16)	0.549 (2)	−0.0066 (13)	0.063 (9)*
N1	0.44634 (15)	−0.01847 (15)	0.63825 (8)	0.0339 (4)
N2	0.66774 (18)	−0.43591 (18)	0.94863 (9)	0.0474 (5)
N3	0.32399 (14)	0.22088 (14)	0.44421 (8)	0.0311 (3)
N4	0.13327 (15)	0.61430 (14)	0.11989 (8)	0.0332 (4)
N5	0.22979 (15)	0.83133 (15)	0.00504 (9)	0.0357 (4)
C1	0.56246 (19)	−0.0201 (2)	0.66090 (11)	0.0418 (5)
H1	0.616518	0.035341	0.634347	0.050*
C2	0.60535 (19)	−0.0993 (2)	0.72121 (11)	0.0417 (5)
H2	0.687050	−0.097234	0.734268	0.050*
C3	0.52771 (18)	−0.18256 (17)	0.76293 (10)	0.0331 (4)
C4	0.40701 (18)	−0.18020 (19)	0.73970 (11)	0.0393 (5)
H4	0.350822	−0.233833	0.765656	0.047*
C5	0.37092 (18)	−0.09847 (19)	0.67830 (11)	0.0393 (5)
H5	0.289795	−0.098811	0.663857	0.047*
C6	0.7144 (2)	−0.3259 (2)	0.92367 (11)	0.0451 (5)
H6	0.780326	−0.305313	0.947374	0.054*
C7	0.67096 (19)	−0.24166 (19)	0.86514 (11)	0.0386 (5)
H7	0.707240	−0.166564	0.850264	0.046*
C8	0.57241 (18)	−0.26897 (18)	0.82815 (10)	0.0342 (4)
C9	0.5219 (2)	−0.3816 (2)	0.85489 (11)	0.0444 (5)
H9A	0.454541	−0.403962	0.833014	0.053*
C10	0.5716 (2)	−0.4605 (2)	0.91394 (12)	0.0514 (6)
H10	0.535930	−0.535569	0.930657	0.062*
C11	0.39719 (18)	0.30579 (18)	0.40608 (11)	0.0373 (5)
H11	0.475641	0.312109	0.422913	0.045*
C12	0.36219 (18)	0.38385 (18)	0.34346 (11)	0.0367 (5)
H12	0.416736	0.440794	0.318790	0.044*
C13	0.24535 (17)	0.37796 (17)	0.31686 (10)	0.0299 (4)
C14	0.16882 (17)	0.29091 (18)	0.35696 (10)	0.0365 (5)
H14	0.089433	0.283600	0.341728	0.044*
C15	0.21083 (17)	0.21556 (19)	0.41926 (10)	0.0366 (5)
H15	0.158001	0.158196	0.445261	0.044*
C16	0.20919 (19)	0.65071 (18)	0.16245 (10)	0.0376 (5)
H16	0.237771	0.729246	0.148137	0.045*
C17	0.24722 (19)	0.57804 (18)	0.22630 (10)	0.0372 (5)
H17	0.300167	0.607670	0.253975	0.045*
C18	0.20611 (16)	0.45990 (17)	0.24934 (10)	0.0301 (4)
C19	0.12639 (18)	0.42283 (18)	0.20528 (10)	0.0345 (4)
H19	0.095861	0.344987	0.218331	0.041*
C20	0.09266 (18)	0.50133 (18)	0.14235 (10)	0.0361 (4)
H20	0.038814	0.474499	0.113901	0.043*
C21	0.3388 (2)	0.7903 (2)	−0.01008 (16)	0.0613 (7)
H21	0.343265	0.715188	−0.019510	0.074*
C22	0.4454 (2)	0.8530 (2)	−0.01252 (17)	0.0668 (8)
H22	0.519350	0.819901	−0.023310	0.080*
C23	0.44329 (18)	0.96475 (18)	0.00095 (11)	0.0361 (4)
C24	0.32980 (19)	1.00692 (19)	0.01651 (12)	0.0419 (5)
H24	0.322945	1.081478	0.026449	0.050*
C25	0.22646 (19)	0.93955 (19)	0.01745 (12)	0.0416 (5)
H25	0.151031	0.971218	0.027200	0.050*
C26	0.29583 (18)	0.25023 (18)	0.60563 (10)	0.0342 (4)
C27	0.24654 (18)	0.33984 (19)	0.64101 (11)	0.0382 (5)
C28	0.3152 (2)	0.4384 (2)	0.64491 (15)	0.0584 (7)
C29	0.2655 (3)	0.5232 (3)	0.67603 (19)	0.0848 (10)
H29	0.309833	0.590962	0.676996	0.102*
C30	0.1514 (3)	0.5073 (3)	0.7053 (2)	0.0926 (11)
H30	0.119079	0.563885	0.726726	0.111*
C31	0.0841 (3)	0.4094 (3)	0.7035 (2)	0.0870 (11)
H31	0.006936	0.398807	0.724094	0.104*
C32	0.1313 (2)	0.3262 (2)	0.67084 (14)	0.0585 (7)
H32	0.084907	0.260227	0.668929	0.070*
C33	0.67051 (16)	0.11563 (17)	0.49469 (9)	0.0278 (4)
C34	0.74627 (17)	0.21332 (16)	0.50758 (9)	0.0289 (4)
C35	0.87402 (18)	0.21315 (18)	0.50003 (11)	0.0368 (5)
C36	0.9411 (2)	0.3034 (2)	0.51642 (14)	0.0539 (6)
H36	1.026195	0.303308	0.511912	0.065*
C37	0.8821 (2)	0.3925 (2)	0.53918 (14)	0.0581 (7)
H37	0.927865	0.451984	0.550389	0.070*
C38	0.7565 (2)	0.3953 (2)	0.54571 (15)	0.0600 (7)
H38	0.717158	0.457127	0.560291	0.072*
C39	0.6895 (2)	0.3055 (2)	0.53040 (13)	0.0454 (5)
H39	0.604491	0.306589	0.535436	0.055*
C40	−0.11856 (18)	0.76483 (18)	0.08531 (10)	0.0351 (4)
C41	−0.2240 (2)	0.7879 (2)	0.12733 (11)	0.0417 (5)
C42	−0.3247 (2)	0.7133 (3)	0.13934 (14)	0.0596 (7)
C43	−0.4237 (3)	0.7394 (4)	0.17739 (19)	0.0996 (12)
H43	−0.491888	0.690437	0.184663	0.119*
C44	−0.4210 (4)	0.8365 (5)	0.2040 (2)	0.1126 (15)
H44	−0.487079	0.852323	0.230315	0.135*
C45	−0.3231 (4)	0.9112 (4)	0.19291 (19)	0.1003 (12)
H45	−0.322902	0.977912	0.210964	0.120*
C46	−0.2246 (3)	0.8869 (3)	0.15467 (14)	0.0654 (7)
H46	−0.157687	0.937517	0.147131	0.079*
C47	0.03259 (19)	0.81423 (19)	−0.13648 (11)	0.0389 (5)
C48	−0.01849 (19)	0.90816 (18)	−0.19807 (10)	0.0369 (5)
C49	0.0107 (2)	0.9058 (2)	−0.26616 (11)	0.0408 (5)
C50	−0.0378 (2)	0.9945 (2)	−0.32279 (12)	0.0532 (6)
H50	−0.018213	0.992567	−0.368002	0.064*
C51	−0.1141 (3)	1.0846 (2)	−0.31211 (13)	0.0557 (6)
H51	−0.146484	1.143341	−0.350112	0.067*
C52	−0.1430 (3)	1.0884 (2)	−0.24526 (13)	0.0585 (7)
H52	−0.194411	1.150024	−0.238205	0.070*
C53	−0.0959 (2)	1.0013 (2)	−0.18913 (12)	0.0492 (6)
H53	−0.116154	1.004531	−0.144223	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02255 (13)	0.02972 (14)	0.03064 (14)	−0.00244 (10)	−0.00050 (10)	−0.01000 (11)
Co2	0.03023 (15)	0.03340 (15)	0.03044 (14)	−0.00662 (11)	−0.00272 (11)	−0.00606 (11)
O1	0.0320 (8)	0.0574 (10)	0.0669 (10)	−0.0087 (7)	0.0140 (7)	−0.0352 (8)
O2	0.0345 (8)	0.0414 (8)	0.0535 (9)	−0.0060 (6)	0.0036 (7)	−0.0236 (7)
O3	0.0613 (13)	0.0969 (17)	0.171 (2)	−0.0421 (12)	0.0432 (14)	−0.0927 (18)
O4	0.0227 (7)	0.0500 (9)	0.0494 (9)	−0.0074 (6)	0.0033 (6)	−0.0153 (7)
O5	0.0289 (7)	0.0325 (7)	0.0456 (8)	−0.0027 (6)	−0.0020 (6)	−0.0167 (6)
O6	0.0283 (8)	0.0663 (11)	0.1028 (15)	−0.0096 (8)	0.0154 (9)	−0.0514 (11)
O7	0.0401 (8)	0.0434 (8)	0.0424 (8)	−0.0058 (6)	−0.0009 (6)	−0.0182 (7)
O8	0.0373 (8)	0.0409 (8)	0.0534 (9)	−0.0087 (7)	0.0015 (7)	−0.0127 (7)
O9	0.0702 (15)	0.1036 (17)	0.1071 (18)	−0.0508 (13)	0.0321 (13)	−0.0558 (15)
O10	0.0473 (9)	0.0540 (9)	0.0305 (8)	−0.0016 (7)	−0.0051 (7)	−0.0036 (7)
O11	0.0608 (11)	0.0557 (10)	0.0417 (9)	0.0114 (8)	−0.0053 (8)	−0.0064 (8)
O12	0.0549 (11)	0.0758 (13)	0.0468 (10)	0.0011 (9)	0.0071 (9)	−0.0164 (10)
O13	0.0557 (10)	0.0367 (8)	0.0393 (9)	0.0024 (7)	−0.0089 (8)	−0.0092 (7)
N1	0.0301 (9)	0.0372 (9)	0.0343 (9)	−0.0013 (7)	−0.0024 (7)	−0.0094 (7)
N2	0.0479 (11)	0.0517 (12)	0.0379 (10)	0.0049 (9)	−0.0037 (9)	−0.0049 (9)
N3	0.0268 (8)	0.0334 (9)	0.0318 (8)	−0.0035 (7)	−0.0002 (7)	−0.0064 (7)
N4	0.0327 (9)	0.0344 (9)	0.0316 (8)	−0.0037 (7)	−0.0008 (7)	−0.0070 (7)
N5	0.0326 (9)	0.0345 (9)	0.0385 (9)	−0.0076 (7)	0.0018 (7)	−0.0068 (7)
C1	0.0350 (11)	0.0470 (13)	0.0396 (11)	−0.0116 (9)	−0.0019 (9)	−0.0040 (10)
C2	0.0302 (11)	0.0512 (13)	0.0409 (12)	−0.0069 (9)	−0.0067 (9)	−0.0073 (10)
C3	0.0331 (10)	0.0342 (10)	0.0336 (10)	−0.0006 (8)	−0.0004 (8)	−0.0118 (8)
C4	0.0303 (11)	0.0445 (12)	0.0394 (11)	−0.0076 (9)	0.0015 (9)	−0.0044 (9)
C5	0.0275 (10)	0.0487 (13)	0.0388 (11)	−0.0029 (9)	−0.0024 (9)	−0.0067 (10)
C6	0.0419 (12)	0.0562 (14)	0.0381 (12)	0.0028 (10)	−0.0074 (10)	−0.0149 (11)
C7	0.0382 (11)	0.0393 (11)	0.0386 (11)	−0.0034 (9)	−0.0020 (9)	−0.0108 (9)
C8	0.0309 (10)	0.0381 (11)	0.0345 (10)	0.0023 (8)	0.0007 (8)	−0.0115 (9)
C9	0.0421 (12)	0.0433 (12)	0.0436 (12)	−0.0082 (10)	−0.0071 (10)	−0.0037 (10)
C10	0.0566 (15)	0.0435 (13)	0.0474 (13)	−0.0068 (11)	−0.0021 (11)	−0.0002 (11)
C11	0.0298 (10)	0.0392 (11)	0.0411 (11)	−0.0077 (8)	−0.0068 (9)	−0.0072 (9)
C12	0.0310 (10)	0.0360 (11)	0.0396 (11)	−0.0102 (8)	−0.0012 (9)	−0.0034 (9)
C13	0.0275 (10)	0.0308 (10)	0.0324 (10)	−0.0008 (8)	0.0002 (8)	−0.0099 (8)
C14	0.0230 (9)	0.0440 (12)	0.0393 (11)	−0.0046 (8)	−0.0035 (8)	−0.0055 (9)
C15	0.0248 (10)	0.0434 (12)	0.0369 (11)	−0.0058 (8)	0.0024 (8)	−0.0023 (9)
C16	0.0434 (12)	0.0323 (11)	0.0352 (11)	−0.0083 (9)	−0.0019 (9)	−0.0053 (9)
C17	0.0386 (11)	0.0370 (11)	0.0366 (11)	−0.0077 (9)	−0.0060 (9)	−0.0105 (9)
C18	0.0257 (9)	0.0331 (10)	0.0312 (10)	−0.0001 (8)	0.0031 (8)	−0.0083 (8)
C19	0.0350 (11)	0.0317 (10)	0.0358 (10)	−0.0074 (8)	0.0002 (8)	−0.0070 (8)
C20	0.0355 (11)	0.0389 (11)	0.0339 (10)	−0.0087 (9)	−0.0038 (8)	−0.0092 (9)
C21	0.0431 (14)	0.0479 (14)	0.106 (2)	−0.0135 (11)	0.0171 (14)	−0.0420 (15)
C22	0.0359 (13)	0.0581 (16)	0.122 (2)	−0.0137 (11)	0.0255 (14)	−0.0501 (17)
C23	0.0341 (11)	0.0350 (11)	0.0393 (11)	−0.0083 (8)	0.0037 (9)	−0.0094 (9)
C24	0.0360 (11)	0.0338 (11)	0.0580 (14)	−0.0054 (9)	0.0032 (10)	−0.0158 (10)
C25	0.0325 (11)	0.0388 (12)	0.0526 (13)	−0.0029 (9)	0.0028 (10)	−0.0109 (10)
C26	0.0299 (10)	0.0381 (11)	0.0357 (10)	−0.0003 (8)	0.0004 (8)	−0.0121 (9)
C27	0.0330 (11)	0.0404 (12)	0.0462 (12)	−0.0006 (9)	0.0023 (9)	−0.0201 (10)
C28	0.0446 (14)	0.0581 (15)	0.0853 (19)	−0.0104 (11)	0.0096 (13)	−0.0407 (14)
C29	0.078 (2)	0.073 (2)	0.129 (3)	−0.0116 (16)	0.013 (2)	−0.071 (2)
C30	0.078 (2)	0.091 (2)	0.138 (3)	0.0048 (18)	0.023 (2)	−0.081 (2)
C31	0.0585 (18)	0.097 (2)	0.128 (3)	−0.0012 (17)	0.0335 (19)	−0.070 (2)
C32	0.0396 (13)	0.0647 (16)	0.0810 (19)	−0.0055 (12)	0.0138 (13)	−0.0363 (15)
C33	0.0254 (10)	0.0308 (10)	0.0246 (9)	−0.0042 (7)	−0.0008 (7)	−0.0029 (7)
C34	0.0272 (9)	0.0293 (10)	0.0302 (10)	−0.0034 (7)	0.0011 (8)	−0.0079 (8)
C35	0.0286 (10)	0.0380 (11)	0.0457 (12)	−0.0073 (8)	0.0062 (9)	−0.0139 (9)
C36	0.0348 (12)	0.0587 (15)	0.0755 (17)	−0.0201 (11)	0.0094 (12)	−0.0292 (13)
C37	0.0599 (16)	0.0484 (14)	0.0749 (18)	−0.0248 (12)	0.0078 (13)	−0.0301 (13)
C38	0.0595 (16)	0.0454 (14)	0.087 (2)	−0.0055 (12)	0.0106 (14)	−0.0386 (14)
C39	0.0342 (11)	0.0426 (12)	0.0652 (15)	−0.0023 (9)	0.0045 (10)	−0.0242 (11)
C40	0.0346 (11)	0.0376 (11)	0.0318 (10)	−0.0014 (9)	−0.0060 (8)	−0.0071 (9)
C41	0.0383 (12)	0.0491 (13)	0.0380 (11)	0.0010 (10)	−0.0012 (9)	−0.0125 (10)
C42	0.0449 (14)	0.084 (2)	0.0532 (15)	−0.0119 (13)	0.0088 (12)	−0.0232 (14)
C43	0.0530 (19)	0.157 (4)	0.094 (3)	−0.018 (2)	0.0313 (18)	−0.042 (3)
C44	0.087 (3)	0.166 (4)	0.095 (3)	0.029 (3)	0.030 (2)	−0.056 (3)
C45	0.116 (3)	0.112 (3)	0.089 (3)	0.033 (3)	0.010 (2)	−0.058 (2)
C46	0.0744 (19)	0.0665 (18)	0.0634 (17)	0.0101 (14)	−0.0003 (14)	−0.0325 (14)
C47	0.0361 (11)	0.0408 (12)	0.0378 (12)	−0.0121 (9)	−0.0052 (9)	−0.0061 (9)
C48	0.0381 (11)	0.0371 (11)	0.0341 (10)	−0.0133 (9)	−0.0041 (9)	−0.0057 (9)
C49	0.0376 (11)	0.0456 (12)	0.0382 (11)	−0.0123 (9)	0.0011 (9)	−0.0088 (10)
C50	0.0615 (16)	0.0614 (16)	0.0324 (12)	−0.0167 (13)	−0.0008 (11)	−0.0041 (11)
C51	0.0699 (17)	0.0436 (14)	0.0453 (14)	−0.0119 (12)	−0.0150 (12)	0.0034 (11)
C52	0.0750 (18)	0.0418 (13)	0.0565 (15)	0.0047 (12)	−0.0135 (13)	−0.0100 (12)
C53	0.0622 (15)	0.0460 (13)	0.0398 (12)	−0.0014 (11)	−0.0079 (11)	−0.0124 (10)

Geometric parameters (Å, º)

Co1—O1	2.1772 (15)	C14—H14	0.9300
Co1—O2	2.1769 (14)	C14—C15	1.377 (3)
Co1—O4	2.0408 (14)	C15—H15	0.9300
Co1—O5^i	2.0686 (13)	C16—H16	0.9300
Co1—N1	2.1412 (16)	C16—C17	1.376 (3)
Co1—N3	2.1421 (16)	C17—H17	0.9300
Co2—O7	2.2348 (15)	C17—C18	1.393 (3)
Co2—O8	2.1135 (15)	C18—C19	1.389 (3)
Co2—O10	2.0739 (14)	C19—H19	0.9300
Co2—O13	2.0717 (16)	C19—C20	1.375 (3)
Co2—N4	2.1568 (16)	C20—H20	0.9300
Co2—N5	2.1177 (16)	C21—H21	0.9300
Co2—C40	2.514 (2)	C21—C22	1.375 (3)
O1—C26	1.270 (2)	C22—H22	0.9300
O2—C26	1.247 (2)	C22—C23	1.379 (3)
O3—H3	0.845 (10)	C23—C23^ii	1.488 (4)
O3—C28	1.346 (3)	C23—C24	1.379 (3)
O4—C33	1.244 (2)	C24—H24	0.9300
O5—C33	1.275 (2)	C24—C25	1.378 (3)
O6—H8	0.838 (10)	C25—H25	0.9300
O6—C35	1.348 (3)	C26—C27	1.484 (3)
O7—C40	1.272 (2)	C27—C28	1.391 (3)
O8—C40	1.254 (2)	C27—C32	1.380 (3)
O9—H13	0.839 (10)	C28—C29	1.386 (4)
O9—C42	1.346 (3)	C29—H29	0.9300
O10—C47	1.261 (3)	C29—C30	1.365 (4)
O11—C47	1.266 (3)	C30—H30	0.9300
O12—H18	0.853 (10)	C30—C31	1.366 (4)
O12—C49	1.348 (3)	C31—H31	0.9300
O13—H26	0.837 (10)	C31—C32	1.379 (4)
O13—H27	0.832 (10)	C32—H32	0.9300
N1—C1	1.341 (3)	C33—C34	1.486 (3)
N1—C5	1.338 (3)	C34—C35	1.398 (3)
N2—C6	1.338 (3)	C34—C39	1.390 (3)
N2—C10	1.333 (3)	C35—C36	1.392 (3)
N3—C11	1.340 (2)	C36—H36	0.9300
N3—C15	1.339 (2)	C36—C37	1.369 (3)
N4—C16	1.338 (3)	C37—H37	0.9300
N4—C20	1.338 (2)	C37—C38	1.373 (4)
N5—C21	1.329 (3)	C38—H38	0.9300
N5—C25	1.330 (3)	C38—C39	1.378 (3)
C1—H1	0.9300	C39—H39	0.9300
C1—C2	1.370 (3)	C40—C41	1.478 (3)
C2—H2	0.9300	C41—C42	1.388 (3)
C2—C3	1.387 (3)	C41—C46	1.386 (3)
C3—C4	1.391 (3)	C42—C43	1.387 (4)
C3—C8	1.479 (3)	C43—H43	0.9300
C4—H4	0.9300	C43—C44	1.358 (6)
C4—C5	1.375 (3)	C44—H44	0.9300
C5—H5	0.9300	C44—C45	1.364 (6)
C6—H6	0.9300	C45—H45	0.9300
C6—C7	1.373 (3)	C45—C46	1.379 (4)
C7—H7	0.9300	C46—H46	0.9300
C7—C8	1.392 (3)	C47—C48	1.494 (3)
C8—C9	1.385 (3)	C48—C49	1.398 (3)
C9—H9A	0.9300	C48—C53	1.392 (3)
C9—C10	1.377 (3)	C49—C50	1.393 (3)
C10—H10	0.9300	C50—H50	0.9300
C11—H11	0.9300	C50—C51	1.369 (4)
C11—C12	1.372 (3)	C51—H51	0.9300
C12—H12	0.9300	C51—C52	1.378 (4)
C12—C13	1.390 (3)	C52—H52	0.9300
C13—C14	1.391 (3)	C52—C53	1.372 (3)
C13—C18	1.474 (3)	C53—H53	0.9300
O2—Co1—O1	59.82 (5)	C18—C17—H17	120.1
O4—Co1—O1	91.69 (6)	C17—C18—C13	121.87 (17)
O4—Co1—O2	151.47 (6)	C19—C18—C13	121.51 (17)
O4—Co1—O5^i	117.97 (6)	C19—C18—C17	116.62 (17)
O4—Co1—N1	91.32 (6)	C18—C19—H19	120.0
O4—Co1—N3	87.16 (6)	C20—C19—C18	119.94 (18)
O5^i—Co1—O1	150.29 (5)	C20—C19—H19	120.0
O5^i—Co1—O2	90.48 (5)	N4—C20—C19	123.42 (18)
O5^i—Co1—N1	89.68 (6)	N4—C20—H20	118.3
O5^i—Co1—N3	89.31 (6)	C19—C20—H20	118.3
N1—Co1—O1	91.38 (6)	N5—C21—H21	118.3
N1—Co1—O2	90.90 (6)	N5—C21—C22	123.4 (2)
N1—Co1—N3	177.53 (6)	C22—C21—H21	118.3
N3—Co1—O1	90.61 (6)	C21—C22—H22	119.8
N3—Co1—O2	91.37 (6)	C21—C22—C23	120.4 (2)
O7—Co2—C40	30.36 (6)	C23—C22—H22	119.8
O8—Co2—O7	60.20 (5)	C22—C23—C23^ii	122.0 (2)
O8—Co2—N4	89.11 (6)	C22—C23—C24	115.94 (19)
O8—Co2—N5	95.55 (6)	C24—C23—C23^ii	122.1 (2)
O8—Co2—C40	29.87 (6)	C23—C24—H24	119.7
O10—Co2—O7	91.19 (6)	C25—C24—C23	120.6 (2)
O10—Co2—O8	93.29 (6)	C25—C24—H24	119.7
O10—Co2—N4	173.40 (6)	N5—C25—C24	122.9 (2)
O10—Co2—N5	93.17 (6)	N5—C25—H25	118.5
O10—Co2—C40	93.68 (6)	C24—C25—H25	118.5
O13—Co2—O7	107.21 (6)	O1—C26—C27	118.92 (18)
O13—Co2—O8	167.09 (6)	O2—C26—O1	119.20 (18)
O13—Co2—O10	89.66 (6)	O2—C26—C27	121.87 (18)
O13—Co2—N4	86.68 (6)	C28—C27—C26	120.90 (19)
O13—Co2—N5	96.83 (7)	C32—C27—C26	120.2 (2)
O13—Co2—C40	137.40 (7)	C32—C27—C28	118.9 (2)
N4—Co2—O7	84.66 (6)	O3—C28—C27	122.1 (2)
N4—Co2—C40	85.34 (6)	O3—C28—C29	118.0 (2)
N5—Co2—O7	155.58 (6)	C29—C28—C27	119.8 (2)
N5—Co2—N4	92.71 (6)	C28—C29—H29	120.0
N5—Co2—C40	125.28 (7)	C30—C29—C28	119.9 (3)
C26—O1—Co1	90.17 (12)	C30—C29—H29	120.0
C26—O2—Co1	90.79 (12)	C29—C30—H30	119.6
C28—O3—H3	105 (3)	C29—C30—C31	120.9 (3)
C33—O4—Co1	165.49 (14)	C31—C30—H30	119.6
C33—O5—Co1^i	117.07 (11)	C30—C31—H31	120.2
C35—O6—H8	110 (2)	C30—C31—C32	119.6 (3)
C40—O7—Co2	87.04 (12)	C32—C31—H31	120.2
C40—O8—Co2	93.04 (12)	C27—C32—H32	119.6
C42—O9—H13	104 (3)	C31—C32—C27	120.7 (2)
C47—O10—Co2	129.12 (15)	C31—C32—H32	119.6
C49—O12—H18	105 (2)	O4—C33—O5	121.83 (17)
Co2—O13—H26	103 (2)	O4—C33—C34	120.09 (17)
Co2—O13—H27	123.7 (19)	O5—C33—C34	118.09 (16)
H26—O13—H27	117 (3)	C35—C34—C33	122.02 (17)
C1—N1—Co1	122.34 (13)	C39—C34—C33	119.26 (17)
C5—N1—Co1	121.01 (13)	C39—C34—C35	118.67 (18)
C5—N1—C1	116.64 (17)	O6—C35—C34	122.54 (18)
C10—N2—C6	115.94 (19)	O6—C35—C36	117.85 (19)
C11—N3—Co1	121.43 (13)	C36—C35—C34	119.59 (19)
C15—N3—Co1	121.58 (13)	C35—C36—H36	119.9
C15—N3—C11	116.95 (16)	C37—C36—C35	120.1 (2)
C16—N4—Co2	124.46 (13)	C37—C36—H36	119.9
C16—N4—C20	116.83 (17)	C36—C37—H37	119.5
C20—N4—Co2	118.69 (13)	C36—C37—C38	121.1 (2)
C21—N5—Co2	123.24 (14)	C38—C37—H37	119.5
C21—N5—C25	116.75 (18)	C37—C38—H38	120.4
C25—N5—Co2	119.69 (14)	C37—C38—C39	119.2 (2)
N1—C1—H1	118.4	C39—C38—H38	120.4
N1—C1—C2	123.22 (19)	C34—C39—H39	119.3
C2—C1—H1	118.4	C38—C39—C34	121.3 (2)
C1—C2—H2	119.8	C38—C39—H39	119.3
C1—C2—C3	120.44 (19)	O7—C40—Co2	62.59 (11)
C3—C2—H2	119.8	O7—C40—C41	119.59 (18)
C2—C3—C4	116.31 (18)	O8—C40—Co2	57.09 (11)
C2—C3—C8	121.21 (18)	O8—C40—O7	119.58 (19)
C4—C3—C8	122.48 (18)	O8—C40—C41	120.83 (19)
C3—C4—H4	120.0	C41—C40—Co2	176.31 (14)
C5—C4—C3	119.91 (19)	C42—C41—C40	121.4 (2)
C5—C4—H4	120.0	C46—C41—C40	120.0 (2)
N1—C5—C4	123.47 (18)	C46—C41—C42	118.6 (2)
N1—C5—H5	118.3	O9—C42—C41	121.9 (2)
C4—C5—H5	118.3	O9—C42—C43	118.2 (3)
N2—C6—H6	118.0	C43—C42—C41	120.0 (3)
N2—C6—C7	124.0 (2)	C42—C43—H43	120.0
C7—C6—H6	118.0	C44—C43—C42	120.0 (3)
C6—C7—H7	120.1	C44—C43—H43	120.0
C6—C7—C8	119.8 (2)	C43—C44—H44	119.4
C8—C7—H7	120.1	C43—C44—C45	121.1 (3)
C7—C8—C3	121.04 (18)	C45—C44—H44	119.4
C9—C8—C3	122.60 (18)	C44—C45—H45	120.3
C9—C8—C7	116.33 (19)	C44—C45—C46	119.5 (3)
C8—C9—H9A	120.1	C46—C45—H45	120.3
C10—C9—C8	119.8 (2)	C41—C46—H46	119.6
C10—C9—H9A	120.1	C45—C46—C41	120.8 (3)
N2—C10—C9	124.1 (2)	C45—C46—H46	119.6
N2—C10—H10	118.0	O10—C47—O11	124.1 (2)
C9—C10—H10	118.0	O10—C47—C48	118.1 (2)
N3—C11—H11	118.4	O11—C47—C48	117.77 (19)
N3—C11—C12	123.28 (18)	C49—C48—C47	121.1 (2)
C12—C11—H11	118.4	C53—C48—C47	120.76 (19)
C11—C12—H12	120.0	C53—C48—C49	118.1 (2)
C11—C12—C13	120.09 (18)	O12—C49—C48	121.4 (2)
C13—C12—H12	120.0	O12—C49—C50	118.5 (2)
C12—C13—C14	116.58 (17)	C50—C49—C48	120.1 (2)
C12—C13—C18	121.10 (17)	C49—C50—H50	119.9
C14—C13—C18	122.32 (17)	C51—C50—C49	120.2 (2)
C13—C14—H14	120.1	C51—C50—H50	119.9
C15—C14—C13	119.89 (17)	C50—C51—H51	119.9
C15—C14—H14	120.1	C50—C51—C52	120.3 (2)
N3—C15—C14	123.20 (18)	C52—C51—H51	119.9
N3—C15—H15	118.4	C51—C52—H52	120.0
C14—C15—H15	118.4	C53—C52—C51	120.0 (2)
N4—C16—H16	118.3	C53—C52—H52	120.0
N4—C16—C17	123.43 (18)	C48—C53—H53	119.3
C17—C16—H16	118.3	C52—C53—C48	121.3 (2)
C16—C17—H17	120.1	C52—C53—H53	119.3
C16—C17—C18	119.76 (18)
Co1—O1—C26—O2	1.3 (2)	C11—N3—C15—C14	1.1 (3)
Co1—O1—C26—C27	−178.48 (17)	C11—C12—C13—C14	0.4 (3)
Co1—O2—C26—O1	−1.3 (2)	C11—C12—C13—C18	−179.31 (19)
Co1—O2—C26—C27	178.48 (18)	C12—C13—C14—C15	−0.5 (3)
Co1—O4—C33—O5	98.2 (6)	C12—C13—C18—C17	−33.3 (3)
Co1—O4—C33—C34	−81.8 (6)	C12—C13—C18—C19	146.4 (2)
Co1^i—O5—C33—O4	0.1 (2)	C13—C14—C15—N3	−0.2 (3)
Co1^i—O5—C33—C34	−179.90 (12)	C13—C18—C19—C20	−179.36 (18)
Co1—N1—C1—C2	−178.47 (17)	C14—C13—C18—C17	147.0 (2)
Co1—N1—C5—C4	178.93 (16)	C14—C13—C18—C19	−33.2 (3)
Co1—N3—C11—C12	−178.99 (16)	C15—N3—C11—C12	−1.2 (3)
Co1—N3—C15—C14	178.79 (16)	C16—N4—C20—C19	−0.9 (3)
Co2—O7—C40—O8	3.61 (18)	C16—C17—C18—C13	179.20 (18)
Co2—O7—C40—C41	−176.61 (17)	C16—C17—C18—C19	−0.6 (3)
Co2—O8—C40—O7	−3.81 (19)	C17—C18—C19—C20	0.4 (3)
Co2—O8—C40—C41	176.41 (16)	C18—C13—C14—C15	179.13 (19)
Co2—O10—C47—O11	13.9 (3)	C18—C19—C20—N4	0.4 (3)
Co2—O10—C47—C48	−166.89 (13)	C20—N4—C16—C17	0.8 (3)
Co2—N4—C16—C17	179.12 (15)	C21—N5—C25—C24	−1.3 (3)
Co2—N4—C20—C19	−179.40 (16)	C21—C22—C23—C23^ii	179.8 (3)
Co2—N5—C21—C22	−172.7 (2)	C21—C22—C23—C24	0.0 (4)
Co2—N5—C25—C24	172.38 (17)	C22—C23—C24—C25	−0.6 (3)
O1—C26—C27—C28	6.0 (3)	C23^ii—C23—C24—C25	179.7 (2)
O1—C26—C27—C32	−173.9 (2)	C23—C24—C25—N5	1.3 (4)
O2—C26—C27—C28	−173.8 (2)	C25—N5—C21—C22	0.8 (4)
O2—C26—C27—C32	6.4 (3)	C26—C27—C28—O3	−2.1 (4)
O3—C28—C29—C30	−177.5 (3)	C26—C27—C28—C29	177.7 (3)
O4—C33—C34—C35	178.91 (18)	C26—C27—C32—C31	−179.6 (3)
O4—C33—C34—C39	1.4 (3)	C27—C28—C29—C30	2.7 (5)
O5—C33—C34—C35	−1.0 (3)	C28—C27—C32—C31	0.6 (4)
O5—C33—C34—C39	−178.55 (18)	C28—C29—C30—C31	−1.0 (6)
O6—C35—C36—C37	−179.0 (2)	C29—C30—C31—C32	−0.9 (6)
O7—C40—C41—C42	−2.6 (3)	C30—C31—C32—C27	1.1 (5)
O7—C40—C41—C46	178.6 (2)	C32—C27—C28—O3	177.8 (3)
O8—C40—C41—C42	177.2 (2)	C32—C27—C28—C29	−2.5 (4)
O8—C40—C41—C46	−1.7 (3)	C33—C34—C35—O6	1.8 (3)
O9—C42—C43—C44	179.5 (4)	C33—C34—C35—C36	−176.5 (2)
O10—C47—C48—C49	−175.88 (19)	C33—C34—C39—C38	177.4 (2)
O10—C47—C48—C53	4.6 (3)	C34—C35—C36—C37	−0.6 (4)
O11—C47—C48—C49	3.4 (3)	C35—C34—C39—C38	−0.2 (3)
O11—C47—C48—C53	−176.1 (2)	C35—C36—C37—C38	−0.6 (4)
O12—C49—C50—C51	179.4 (2)	C36—C37—C38—C39	1.3 (4)
N1—C1—C2—C3	−0.8 (3)	C37—C38—C39—C34	−0.9 (4)
N2—C6—C7—C8	0.0 (3)	C39—C34—C35—O6	179.3 (2)
N3—C11—C12—C13	0.6 (3)	C39—C34—C35—C36	1.0 (3)
N4—C16—C17—C18	0.0 (3)	C40—C41—C42—O9	1.0 (4)
N5—C21—C22—C23	−0.1 (5)	C40—C41—C42—C43	−178.2 (3)
C1—N1—C5—C4	−0.4 (3)	C40—C41—C46—C45	178.8 (3)
C1—C2—C3—C4	0.2 (3)	C41—C42—C43—C44	−1.3 (5)
C1—C2—C3—C8	179.9 (2)	C42—C41—C46—C45	−0.1 (4)
C2—C3—C4—C5	0.2 (3)	C42—C43—C44—C45	1.3 (7)
C2—C3—C8—C7	26.8 (3)	C43—C44—C45—C46	−0.8 (7)
C2—C3—C8—C9	−151.4 (2)	C44—C45—C46—C41	0.2 (5)
C3—C4—C5—N1	−0.1 (3)	C46—C41—C42—O9	179.9 (3)
C3—C8—C9—C10	176.7 (2)	C46—C41—C42—C43	0.7 (4)
C4—C3—C8—C7	−153.5 (2)	C47—C48—C49—O12	0.8 (3)
C4—C3—C8—C9	28.2 (3)	C47—C48—C49—C50	−179.83 (19)
C5—N1—C1—C2	0.8 (3)	C47—C48—C53—C52	179.7 (2)
C6—N2—C10—C9	1.4 (4)	C48—C49—C50—C51	0.1 (3)
C6—C7—C8—C3	−176.81 (19)	C49—C48—C53—C52	0.2 (3)
C6—C7—C8—C9	1.6 (3)	C49—C50—C51—C52	0.3 (4)
C7—C8—C9—C10	−1.6 (3)	C50—C51—C52—C53	−0.4 (4)
C8—C3—C4—C5	−179.44 (19)	C51—C52—C53—C48	0.2 (4)
C8—C9—C10—N2	0.1 (4)	C53—C48—C49—O12	−179.7 (2)
C10—N2—C6—C7	−1.5 (3)	C53—C48—C49—C50	−0.3 (3)

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

Hydrogen-bond geometry (Å, º)

Cg4, Cg7 and Cg9 are the centroids of the N4/C16–C20, C34–C39 and C48–C53 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.85 (3)	1.77 (3)	2.553 (3)	153 (4)
O6—H8···O5	0.84 (2)	1.86 (2)	2.587 (2)	145 (2)
O9—H13···O7	0.84 (2)	1.79 (2)	2.568 (3)	152 (4)
O12—H18···O11	0.85 (2)	1.74 (2)	2.531 (2)	154 (3)
O13—H26···O11	0.84 (1)	1.82 (2)	2.625 (2)	160 (2)
O13—H27···N2^i	0.83 (2)	2.05 (2)	2.860 (3)	167 (2)
C25—H25···O8	0.93	2.55	3.143 (3)	122
C39—H39···O1	0.93	2.38	3.271 (3)	160
C5—H5···O12^iii	0.93	2.59	3.324 (3)	136
C6—H6···O7^iv	0.93	2.48	3.300 (3)	147
C12—H12···O3^v	0.93	2.58	3.173 (3)	122
C15—H15···O6^vi	0.93	2.51	3.292 (3)	142
C2—H2···Cg9^iv	0.93	2.95	3.833 (2)	160
C31—H31···Cg4^vii	0.93	2.85	3.681 (4)	149
C51—H51···Cg7^viii	0.93	2.72	3.623 (3)	165

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