Bis[bis-(2,2'-bi-pyridine-κ(2) N,N')(carbon-ato-κ(2) O,O')cobalt(III)] 2-{4-[(carboxyl-atometh-yl)carbamo-yl]benz-amido}-acetate hexa-hydrate.

The complex cation of the title compound, [Co(CO3)(C10H8N2)2]2(C12H10N2O6)·6H2O, contains a Co(III) atom with a distorted octa-hedral coordination environment formed by four N atoms from two bidentate 2,2'-bi-pyridine ligands and one bidentate carbonate anion. The asymmetric unit is completed by one-half of the 2-({4-[(carboxyl-atometh-yl)carbamo-yl]phen-yl}formamido)-acetate dianion, which is located on a centre of inversion, and by three water mol-ecules. Two [Co(CO3)(C10H8N2)2](+) cations are connected through C-H⋯O contacts by the uncoordinating anions. The aromatic rings of the 2,2'-bi-pyridine ligands and di-acetate anions are involved in π-π stacking and C-H⋯π inter-actions. The centroid-centroid distances are in the range 3.4898 (4)-3.6384 (5) Å. The crystal structure is stabilized by further O-H⋯O and N-H⋯O hydrogen bonds, which give rise to a three-dimensional supra-molecular network.

Related literature

For related crystal structures of transition metals with 2,2′-(terephthaloylbis(aza­nedi­yl))di­acetate, see: Duan et al. (2010 ▶); Kostakis et al. (2005 ▶, 2011 ▶); Wisser et al. (2008 ▶); Zhang & You (2005 ▶); Zhang et al. (2006 ▶). For structures containing the [Co(C10H8N2)2(CO3)] cation, see: Baca et al. (2005 ▶); Lv et al. (2007 ▶); Ma et al. (2008 ▶); Wojciechowska & Daszkiewicz (2010 ▶). For cds networks, see: Delgado Friedrichs et al. (2003 ▶). For π–π and C–H⋯π inter­actions, see: Janiak (2000 ▶); Meyer et al. (2003 ▶); Salonen et al. (2011 ▶). For coordination polymers including metal-organic frameworks, see: Allendorf et al. (2009 ▶); Cook et al. (2013 ▶); Schneider (2009 ▶); Yamada et al. (2013 ▶). For C—H⋯O hydrogen bonds, see: Desiraju (1991 ▶, 2005 ▶); Steiner (1996 ▶, 1997 ▶). For details of the preparation, see: Cleaver & Pratt (1955 ▶).

Experimental

Crystal data

[Co(CO3)(C10H8N2)2]2(C12H10N2O6)·6H2O

M = 1248.94

Triclinic,

a = 10.2198 (13) Å

b = 12.1702 (15) Å

c = 12.4767 (15) Å

α = 118.119 (9)°

β = 93.936 (10)°

γ = 101.84 (1)°

V = 1314.7 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.72 mm−1

T = 223 K

0.22 × 0.21 × 0.20 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: numerical (X-AREA; Stoe, 2008) ▶ T min = 0.801, T max = 0.851

14081 measured reflections

5094 independent reflections

4333 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.106

S = 1.05

5094 reflections

487 parameters

All H-atom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.71 e Å−3

Data collection: X-AREA (Stoe, 2008 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681400631X/wm5010sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400631X/wm5010Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400631X/wm5010Isup3.cdx

CCDC reference: 992984

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Co(CO3)(C10H8N2)2]2(C12H10N2O6)·6H2O	Z = 1
Mr = 1248.94	F(000) = 1292
Triclinic, P1	Dx = 1.577 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2198 (13) Å	Cell parameters from 5094 reflections
b = 12.1702 (15) Å	θ = 1.0–26°
c = 12.4767 (15) Å	µ = 0.72 mm−1
α = 118.119 (9)°	T = 223 K
β = 93.936 (10)°	Block, dark red
γ = 101.84 (1)°	0.22 × 0.21 × 0.20 mm
V = 1314.7 (3) Å3

Stoe IPDS 2 diffractometer	5094 independent reflections
Radiation source: fine-focus sealed tube	4333 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: numerical (X-AREA; Stoe, 2008)	h = −12→12
Tmin = 0.801, Tmax = 0.851	k = −15→15
14081 measured reflections	l = −15→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.6944P] where P = (Fo2 + 2Fc2)/3
5094 reflections	(Δ/σ)max = 0.001
487 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.71 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
Co	0.21576 (3)	0.13013 (3)	0.85140 (3)	0.01767 (11)
O1	0.28625 (18)	0.19311 (17)	1.02079 (16)	0.0237 (4)
O2	0.40218 (17)	0.13060 (17)	0.87431 (16)	0.0247 (4)
O3	0.50087 (19)	0.18433 (19)	1.06633 (18)	0.0319 (4)
O4	0.2036 (2)	0.5200 (2)	0.5181 (2)	0.0471 (6)
O5	0.2900 (2)	0.3522 (2)	0.4300 (2)	0.0463 (6)
O6	0.3510 (3)	0.6605 (2)	0.26307 (19)	0.0431 (5)
O7	0.0512 (4)	0.5777 (3)	0.2127 (4)	0.0641 (8)
H7A	0.137 (6)	0.590 (5)	0.221 (5)	0.078 (17)*
H7B	0.041 (6)	0.584 (6)	0.277 (6)	0.10 (2)*
O8	0.4733 (3)	0.2331 (3)	0.3056 (3)	0.0498 (6)
H8A	0.414 (5)	0.263 (4)	0.334 (4)	0.060 (13)*
H8B	0.475 (4)	0.218 (4)	0.237 (4)	0.042 (10)*
O9	0.0237 (3)	0.6356 (3)	0.4544 (3)	0.0517 (7)
H9A	−0.049 (5)	0.597 (5)	0.466 (5)	0.075 (15)*
H9B	0.082 (6)	0.617 (5)	0.478 (5)	0.078 (17)*
N1	0.1557 (2)	−0.04188 (19)	0.82682 (19)	0.0211 (4)
N2	0.0283 (2)	0.1307 (2)	0.86728 (19)	0.0212 (4)
N3	0.1847 (2)	0.07228 (19)	0.67539 (19)	0.0198 (4)
N4	0.2688 (2)	0.2999 (2)	0.8673 (2)	0.0214 (4)
N5	0.3909 (3)	0.6596 (2)	0.4424 (3)	0.0326 (5)
H5A	0.414 (3)	0.695 (3)	0.510 (3)	0.031 (9)*
C1	0.4045 (2)	0.1708 (2)	0.9927 (2)	0.0222 (5)
C2	0.2320 (3)	−0.1265 (3)	0.8002 (3)	0.0271 (5)
H2	0.320 (3)	−0.095 (3)	0.794 (3)	0.019 (7)*
C3	0.1780 (3)	−0.2506 (3)	0.7780 (3)	0.0338 (6)
H3	0.234 (3)	−0.308 (3)	0.755 (3)	0.033 (8)*
C4	0.0441 (3)	−0.2879 (3)	0.7877 (3)	0.0365 (7)
H4	0.010 (3)	−0.366 (3)	0.780 (3)	0.035 (8)*
C5	−0.0343 (3)	−0.2007 (3)	0.8171 (3)	0.0309 (6)
H5	−0.124 (4)	−0.225 (3)	0.825 (3)	0.036 (9)*
C6	0.0243 (2)	−0.0784 (2)	0.8355 (2)	0.0211 (5)
C7	−0.0479 (2)	0.0219 (2)	0.8617 (2)	0.0208 (5)
C8	−0.1824 (3)	0.0089 (3)	0.8773 (2)	0.0280 (5)
H8	−0.229 (3)	−0.064 (3)	0.875 (3)	0.019 (7)*
C9	−0.2409 (3)	0.1084 (3)	0.8980 (3)	0.0356 (7)
H9	−0.334 (3)	0.099 (3)	0.909 (3)	0.036 (8)*
C10	−0.1639 (3)	0.2174 (3)	0.9019 (3)	0.0372 (7)
H10	−0.200 (3)	0.285 (3)	0.908 (3)	0.037 (9)*
C11	−0.0297 (3)	0.2267 (3)	0.8866 (3)	0.0283 (6)
H11	0.026 (3)	0.304 (3)	0.890 (3)	0.030 (8)*
C12	0.1403 (3)	−0.0507 (2)	0.5811 (2)	0.0250 (5)
H12	0.115 (3)	−0.121 (3)	0.602 (3)	0.024 (7)*
C13	0.1368 (3)	−0.0807 (3)	0.4597 (2)	0.0289 (6)
H13	0.102 (3)	−0.177 (3)	0.392 (3)	0.035 (8)*
C14	0.1773 (3)	0.0183 (3)	0.4329 (3)	0.0323 (6)
H14	0.177 (3)	−0.001 (3)	0.357 (3)	0.030 (8)*
C15	0.2186 (3)	0.1458 (3)	0.5287 (3)	0.0289 (6)
H15	0.250 (3)	0.217 (3)	0.514 (3)	0.038 (9)*
C16	0.2210 (2)	0.1699 (2)	0.6487 (2)	0.0214 (5)
C17	0.2658 (2)	0.2992 (2)	0.7585 (2)	0.0216 (5)
C18	0.3014 (3)	0.4133 (3)	0.7543 (3)	0.0325 (6)
H18	0.295 (4)	0.408 (4)	0.675 (4)	0.056 (11)*
C19	0.3429 (3)	0.5296 (3)	0.8646 (3)	0.0375 (7)
H19	0.372 (3)	0.613 (3)	0.871 (3)	0.038 (9)*
C20	0.3474 (3)	0.5293 (3)	0.9753 (3)	0.0320 (6)
H20	0.372 (4)	0.604 (4)	1.049 (4)	0.046 (10)*
C21	0.3088 (3)	0.4127 (2)	0.9739 (3)	0.0262 (5)
H21	0.310 (3)	0.410 (3)	1.045 (3)	0.024 (7)*
C22	0.2783 (3)	0.4602 (3)	0.4507 (3)	0.0308 (6)
C23	0.3609 (4)	0.5196 (3)	0.3847 (3)	0.0370 (7)
H23A	0.445 (5)	0.497 (4)	0.378 (4)	0.067 (13)*
H23B	0.313 (4)	0.484 (4)	0.299 (4)	0.046 (10)*
C24	0.3921 (3)	0.7198 (3)	0.3761 (3)	0.0280 (6)
C25	0.4476 (2)	0.8647 (3)	0.4443 (2)	0.0251 (5)
C26	0.4791 (3)	0.9241 (3)	0.3728 (3)	0.0266 (5)
H26	0.471 (3)	0.873 (3)	0.288 (3)	0.026 (7)*
C27	0.4691 (3)	0.9436 (3)	0.5722 (3)	0.0270 (5)
H27	0.449 (3)	0.902 (3)	0.620 (3)	0.032 (8)*

	U11	U22	U33	U12	U13	U23
Co	0.01697 (17)	0.01872 (17)	0.01930 (18)	0.00522 (12)	0.00537 (12)	0.01058 (13)
O1	0.0240 (9)	0.0276 (9)	0.0224 (9)	0.0086 (7)	0.0069 (7)	0.0138 (7)
O2	0.0211 (8)	0.0298 (9)	0.0252 (9)	0.0072 (7)	0.0075 (7)	0.0148 (8)
O3	0.0260 (9)	0.0385 (11)	0.0305 (10)	0.0080 (8)	0.0008 (8)	0.0175 (9)
O4	0.0482 (13)	0.0428 (12)	0.0563 (15)	0.0148 (10)	0.0271 (11)	0.0263 (12)
O5	0.0538 (14)	0.0439 (13)	0.0660 (16)	0.0205 (11)	0.0268 (12)	0.0418 (12)
O6	0.0620 (15)	0.0367 (11)	0.0270 (11)	0.0028 (10)	0.0031 (10)	0.0179 (9)
O7	0.064 (2)	0.0615 (18)	0.076 (2)	0.0043 (15)	0.0015 (16)	0.0475 (17)
O8	0.0623 (17)	0.0619 (16)	0.0335 (13)	0.0327 (14)	0.0063 (12)	0.0242 (12)
O9	0.0511 (15)	0.0494 (15)	0.0754 (19)	0.0170 (13)	0.0267 (14)	0.0441 (15)
N1	0.0235 (10)	0.0216 (10)	0.0206 (10)	0.0064 (8)	0.0048 (8)	0.0122 (8)
N2	0.0221 (10)	0.0254 (10)	0.0196 (10)	0.0084 (8)	0.0054 (8)	0.0130 (9)
N3	0.0179 (9)	0.0220 (10)	0.0213 (10)	0.0070 (8)	0.0060 (8)	0.0112 (8)
N4	0.0198 (10)	0.0228 (10)	0.0247 (11)	0.0060 (8)	0.0068 (8)	0.0137 (9)
N5	0.0426 (14)	0.0283 (12)	0.0278 (14)	0.0033 (10)	0.0044 (11)	0.0173 (11)
C1	0.0216 (11)	0.0218 (11)	0.0244 (12)	0.0023 (9)	0.0034 (9)	0.0138 (10)
C2	0.0274 (13)	0.0279 (13)	0.0279 (13)	0.0132 (11)	0.0059 (10)	0.0131 (11)
C3	0.0429 (16)	0.0256 (13)	0.0337 (15)	0.0145 (12)	0.0043 (12)	0.0138 (12)
C4	0.0481 (18)	0.0186 (13)	0.0374 (16)	0.0038 (12)	0.0003 (13)	0.0127 (12)
C5	0.0328 (15)	0.0251 (13)	0.0301 (14)	0.0007 (11)	0.0027 (11)	0.0134 (11)
C6	0.0212 (11)	0.0218 (11)	0.0184 (11)	0.0028 (9)	0.0028 (9)	0.0098 (10)
C7	0.0195 (11)	0.0254 (12)	0.0163 (11)	0.0046 (9)	0.0018 (9)	0.0102 (10)
C8	0.0216 (12)	0.0395 (15)	0.0276 (13)	0.0036 (11)	0.0054 (10)	0.0221 (12)
C9	0.0240 (13)	0.0542 (18)	0.0369 (16)	0.0172 (13)	0.0121 (11)	0.0256 (14)
C10	0.0311 (15)	0.0459 (17)	0.0451 (17)	0.0240 (13)	0.0148 (13)	0.0244 (15)
C11	0.0277 (13)	0.0278 (13)	0.0349 (15)	0.0129 (11)	0.0104 (11)	0.0173 (12)
C12	0.0227 (12)	0.0233 (12)	0.0231 (13)	0.0071 (10)	0.0026 (10)	0.0069 (10)
C13	0.0276 (13)	0.0323 (14)	0.0210 (12)	0.0117 (11)	0.0027 (10)	0.0076 (11)
C14	0.0282 (14)	0.0476 (17)	0.0211 (13)	0.0135 (12)	0.0050 (10)	0.0158 (13)
C15	0.0274 (13)	0.0364 (15)	0.0269 (13)	0.0076 (11)	0.0064 (10)	0.0190 (12)
C16	0.0159 (10)	0.0256 (12)	0.0249 (12)	0.0044 (9)	0.0036 (9)	0.0148 (10)
C17	0.0181 (11)	0.0243 (12)	0.0249 (12)	0.0049 (9)	0.0044 (9)	0.0144 (11)
C18	0.0312 (14)	0.0308 (14)	0.0390 (16)	0.0027 (11)	0.0022 (12)	0.0230 (13)
C19	0.0367 (15)	0.0229 (14)	0.0501 (19)	0.0041 (12)	−0.0023 (13)	0.0190 (13)
C20	0.0271 (13)	0.0227 (13)	0.0381 (16)	0.0068 (11)	−0.0011 (11)	0.0097 (12)
C21	0.0258 (13)	0.0242 (12)	0.0255 (13)	0.0075 (10)	0.0045 (10)	0.0097 (11)
C22	0.0295 (13)	0.0341 (14)	0.0310 (14)	0.0044 (11)	0.0036 (11)	0.0199 (12)
C23	0.0492 (18)	0.0299 (15)	0.0372 (17)	0.0089 (13)	0.0161 (14)	0.0206 (13)
C24	0.0259 (13)	0.0342 (14)	0.0279 (14)	0.0101 (11)	0.0087 (10)	0.0172 (12)
C25	0.0205 (11)	0.0331 (13)	0.0287 (13)	0.0107 (10)	0.0072 (10)	0.0191 (11)
C26	0.0256 (13)	0.0339 (14)	0.0247 (13)	0.0107 (11)	0.0087 (10)	0.0165 (11)
C27	0.0280 (13)	0.0354 (14)	0.0282 (13)	0.0108 (11)	0.0115 (10)	0.0224 (12)

Co—O1	1.9002 (18)	C7—C8	1.389 (3)
Co—O2	1.9054 (17)	C8—C9	1.384 (4)
Co—N1	1.922 (2)	C8—H8	0.91 (3)
Co—N4	1.934 (2)	C9—C10	1.373 (5)
Co—N2	1.940 (2)	C9—H9	0.97 (3)
Co—N3	1.943 (2)	C10—C11	1.387 (4)
Co—C1	2.322 (3)	C10—H10	0.94 (3)
O1—C1	1.326 (3)	C11—H11	0.97 (3)
O2—C1	1.316 (3)	C12—C13	1.377 (4)
O3—C1	1.228 (3)	C12—H12	0.99 (3)
O4—C22	1.248 (4)	C13—C14	1.388 (4)
O5—C22	1.248 (4)	C13—H13	1.04 (3)
O6—C24	1.234 (3)	C14—C15	1.389 (4)
O7—H7A	0.85 (6)	C14—H14	0.87 (3)
O7—H7B	0.79 (7)	C15—C16	1.380 (4)
O8—H8A	0.79 (5)	C15—H15	0.96 (4)
O8—H8B	0.79 (4)	C16—C17	1.466 (3)
O9—H9A	0.86 (5)	C17—C18	1.388 (4)
O9—H9B	0.76 (5)	C18—C19	1.383 (4)
N1—C2	1.349 (3)	C18—H18	0.95 (4)
N1—C6	1.354 (3)	C19—C20	1.381 (5)
N2—C11	1.347 (3)	C19—H19	0.95 (4)
N2—C7	1.359 (3)	C20—C21	1.383 (4)
N3—C12	1.348 (3)	C20—H20	0.90 (4)
N3—C16	1.368 (3)	C21—H21	0.91 (3)
N4—C21	1.340 (3)	C22—O5	1.248 (4)
N4—C17	1.352 (3)	C22—O4	1.248 (4)
N5—C24	1.338 (4)	C22—C23	1.523 (4)
N5—C23	1.454 (4)	C23—H23A	0.95 (4)
N5—H5A	0.74 (4)	C23—H23B	0.98 (4)
C2—C3	1.380 (4)	C24—O6	1.234 (3)
C2—H2	0.93 (3)	C24—C25	1.505 (4)
C3—C4	1.384 (5)	C25—C27	1.391 (4)
C3—H3	0.94 (3)	C25—C26	1.405 (4)
C4—C5	1.388 (4)	C26—C27i	1.380 (4)
C4—H4	0.90 (4)	C26—H26	0.92 (3)
C5—C6	1.385 (4)	C27—C26i	1.380 (4)
C5—H5	0.94 (4)	C27—H27	0.95 (3)
C6—C7	1.473 (3)
O1—Co—O2	69.28 (8)	C10—C9—C8	118.7 (3)
O1—Co—N1	89.82 (8)	C10—C9—H9	122.4 (19)
O2—Co—N1	91.79 (8)	C8—C9—H9	119 (2)
O1—Co—N4	93.35 (8)	C9—C10—C11	120.0 (3)
O2—Co—N4	90.33 (8)	C9—C10—H10	123 (2)
N1—Co—N4	176.66 (9)	C11—C10—H10	117 (2)
O1—Co—N2	97.26 (8)	N2—C11—C10	121.6 (3)
O2—Co—N2	165.72 (8)	N2—C11—H11	118.0 (18)
N1—Co—N2	83.18 (9)	C10—C11—H11	120.4 (18)
N4—Co—N2	95.35 (9)	N3—C12—C13	121.8 (3)
O1—Co—N3	167.67 (8)	N3—C12—H12	118.0 (17)
O2—Co—N3	98.81 (8)	C13—C12—H12	120.1 (17)
N1—Co—N3	93.85 (9)	C12—C13—C14	119.3 (3)
N4—Co—N3	83.28 (9)	C12—C13—H13	117.8 (19)
N2—Co—N3	94.86 (8)	C14—C13—H13	122.9 (19)
O1—Co—C1	34.83 (8)	C13—C14—C15	119.5 (3)
O2—Co—C1	34.52 (8)	C13—C14—H14	119 (2)
N1—Co—C1	89.28 (9)	C15—C14—H14	121 (2)
N4—Co—C1	93.93 (9)	C16—C15—C14	118.6 (3)
N2—Co—C1	131.67 (9)	C16—C15—H15	119 (2)
N3—Co—C1	133.34 (8)	C14—C15—H15	122 (2)
C1—O1—Co	90.26 (14)	N3—C16—C15	122.0 (2)
C1—O2—Co	90.34 (14)	N3—C16—C17	113.7 (2)
H7A—O7—H7B	100 (5)	C15—C16—C17	124.3 (2)
H8A—O8—H8B	115 (4)	N4—C17—C18	121.5 (2)
H9A—O9—H9B	106 (5)	N4—C17—C16	114.4 (2)
C2—N1—C6	119.2 (2)	C18—C17—C16	124.1 (2)
C2—N1—Co	125.61 (19)	C19—C18—C17	118.7 (3)
C6—N1—Co	115.20 (16)	C19—C18—H18	123 (2)
C11—N2—C7	118.7 (2)	C17—C18—H18	118 (2)
C11—N2—Co	127.23 (18)	C20—C19—C18	119.4 (3)
C7—N2—Co	114.07 (16)	C20—C19—H19	116 (2)
C12—N3—C16	118.7 (2)	C18—C19—H19	125 (2)
C12—N3—Co	127.23 (18)	C19—C20—C21	119.4 (3)
C16—N3—Co	113.90 (16)	C19—C20—H20	122 (2)
C21—N4—C17	119.6 (2)	C21—C20—H20	119 (2)
C21—N4—Co	125.91 (19)	N4—C21—C20	121.4 (3)
C17—N4—Co	114.51 (16)	N4—C21—H21	117.4 (19)
C24—N5—C23	122.3 (3)	C20—C21—H21	121.2 (19)
C24—N5—H5A	123 (3)	O5—C22—O4	125.3 (3)
C23—N5—H5A	114 (3)	O5—C22—O4	125.3 (3)
O3—C1—O2	125.3 (2)	O5—C22—O4	125.3 (3)
O3—C1—O1	124.8 (2)	O5—C22—O4	125.3 (3)
O2—C1—O1	109.9 (2)	O5—C22—C23	115.8 (3)
O3—C1—Co	175.78 (19)	O5—C22—C23	115.8 (3)
O2—C1—Co	55.14 (11)	O4—C22—C23	119.0 (3)
O1—C1—Co	54.91 (12)	O4—C22—C23	119.0 (3)
N1—C2—C3	121.5 (3)	N5—C23—C22	115.3 (3)
N1—C2—H2	114.3 (17)	N5—C23—H23A	108 (3)
C3—C2—H2	124.1 (17)	C22—C23—H23A	110 (3)
C2—C3—C4	119.4 (3)	N5—C23—H23B	107 (2)
C2—C3—H3	118 (2)	C22—C23—H23B	111 (2)
C4—C3—H3	122 (2)	H23A—C23—H23B	106 (3)
C3—C4—C5	119.4 (3)	O6—C24—N5	122.2 (3)
C3—C4—H4	120 (2)	O6—C24—N5	122.2 (3)
C5—C4—H4	120 (2)	O6—C24—C25	120.2 (3)
C6—C5—C4	118.7 (3)	O6—C24—C25	120.2 (3)
C6—C5—H5	122 (2)	N5—C24—C25	117.5 (2)
C4—C5—H5	120 (2)	C27—C25—C26	118.0 (3)
N1—C6—C5	121.8 (2)	C27—C25—C24	124.9 (2)
N1—C6—C7	113.5 (2)	C26—C25—C24	117.1 (2)
C5—C6—C7	124.7 (2)	C27i—C26—C25	121.0 (3)
N2—C7—C8	121.6 (2)	C27i—C26—H26	119 (2)
N2—C7—C6	113.9 (2)	C25—C26—H26	119 (2)
C8—C7—C6	124.5 (2)	C26i—C27—C25	121.1 (3)
C9—C8—C7	119.4 (3)	C26i—C27—H27	121.7 (19)
C9—C8—H8	121.6 (17)	C25—C27—H27	117.2 (19)
C7—C8—H8	119.0 (17)
O2—Co—O1—C1	−2.99 (13)	C2—N1—C6—C5	−0.4 (4)
N1—Co—O1—C1	89.00 (14)	Co—N1—C6—C5	178.4 (2)
N4—Co—O1—C1	−92.08 (14)	C2—N1—C6—C7	−178.5 (2)
N2—Co—O1—C1	172.09 (14)	Co—N1—C6—C7	0.3 (3)
N3—Co—O1—C1	−18.4 (4)	C4—C5—C6—N1	−0.7 (4)
O1—Co—O2—C1	3.01 (13)	C4—C5—C6—C7	177.2 (3)
N1—Co—O2—C1	−86.12 (14)	C11—N2—C7—C8	−1.0 (4)
N4—Co—O2—C1	96.46 (14)	Co—N2—C7—C8	176.95 (19)
N2—Co—O2—C1	−17.2 (4)	C11—N2—C7—C6	177.8 (2)
N3—Co—O2—C1	179.71 (14)	Co—N2—C7—C6	−4.3 (3)
O1—Co—N1—C2	−86.1 (2)	N1—C6—C7—N2	2.6 (3)
O2—Co—N1—C2	−16.8 (2)	C5—C6—C7—N2	−175.4 (2)
N2—Co—N1—C2	176.6 (2)	N1—C6—C7—C8	−178.7 (2)
N3—Co—N1—C2	82.2 (2)	C5—C6—C7—C8	3.3 (4)
C1—Co—N1—C2	−51.2 (2)	N2—C7—C8—C9	0.5 (4)
O1—Co—N1—C6	95.23 (18)	C6—C7—C8—C9	−178.1 (3)
O2—Co—N1—C6	164.50 (18)	C7—C8—C9—C10	0.3 (4)
N2—Co—N1—C6	−2.10 (17)	C8—C9—C10—C11	−0.7 (5)
N3—Co—N1—C6	−96.54 (18)	C7—N2—C11—C10	0.6 (4)
C1—Co—N1—C6	130.06 (18)	Co—N2—C11—C10	−177.0 (2)
O1—Co—N2—C11	92.3 (2)	C9—C10—C11—N2	0.2 (5)
O2—Co—N2—C11	111.3 (4)	C16—N3—C12—C13	3.1 (3)
N1—Co—N2—C11	−178.7 (2)	Co—N3—C12—C13	−172.50 (18)
N4—Co—N2—C11	−1.7 (2)	N3—C12—C13—C14	−1.3 (4)
N3—Co—N2—C11	−85.4 (2)	C12—C13—C14—C15	−1.0 (4)
C1—Co—N2—C11	98.4 (2)	C13—C14—C15—C16	1.5 (4)
O1—Co—N2—C7	−85.37 (17)	C12—N3—C16—C15	−2.6 (3)
O2—Co—N2—C7	−66.4 (4)	Co—N3—C16—C15	173.61 (19)
N1—Co—N2—C7	3.57 (17)	C12—N3—C16—C17	179.2 (2)
N4—Co—N2—C7	−179.45 (17)	Co—N3—C16—C17	−4.6 (2)
N3—Co—N2—C7	96.87 (17)	C14—C15—C16—N3	0.3 (4)
C1—Co—N2—C7	−79.34 (19)	C14—C15—C16—C17	178.3 (2)
O1—Co—N3—C12	105.1 (4)	C21—N4—C17—C18	−1.0 (4)
O2—Co—N3—C12	90.5 (2)	Co—N4—C17—C18	−179.89 (19)
N1—Co—N3—C12	−1.9 (2)	C21—N4—C17—C16	179.7 (2)
N4—Co—N3—C12	179.8 (2)	Co—N4—C17—C16	0.8 (3)
N2—Co—N3—C12	−85.4 (2)	N3—C16—C17—N4	2.5 (3)
C1—Co—N3—C12	90.7 (2)	C15—C16—C17—N4	−175.6 (2)
O1—Co—N3—C16	−70.7 (4)	N3—C16—C17—C18	−176.8 (2)
O2—Co—N3—C16	−85.28 (16)	C15—C16—C17—C18	5.1 (4)
N1—Co—N3—C16	−177.70 (16)	N4—C17—C18—C19	1.2 (4)
N4—Co—N3—C16	4.01 (16)	C16—C17—C18—C19	−179.6 (2)
N2—Co—N3—C16	98.84 (16)	C17—C18—C19—C20	−0.3 (4)
C1—Co—N3—C16	−85.06 (18)	C18—C19—C20—C21	−0.7 (4)
O1—Co—N4—C21	−13.4 (2)	C17—N4—C21—C20	−0.1 (4)
O2—Co—N4—C21	−82.6 (2)	Co—N4—C21—C20	178.68 (19)
N2—Co—N4—C21	84.3 (2)	C19—C20—C21—N4	1.0 (4)
N3—Co—N4—C21	178.5 (2)	O5—O5—C22—O4	0.0 (8)
C1—Co—N4—C21	−48.2 (2)	O5—O5—C22—O4	0.0 (8)
O1—Co—N4—C17	165.49 (16)	O5—O5—C22—C23	0.0 (8)
O2—Co—N4—C17	96.23 (17)	O4—O4—C22—O5	0.0 (3)
N2—Co—N4—C17	−96.89 (17)	O4—O4—C22—O5	0.0 (3)
N3—Co—N4—C17	−2.61 (16)	O4—O4—C22—C23	0.0 (5)
C1—Co—N4—C17	130.59 (17)	C24—N5—C23—C22	−142.9 (3)
Co—O2—C1—O3	174.9 (2)	O5—C22—C23—N5	−156.8 (3)
Co—O2—C1—O1	−4.29 (19)	O5—C22—C23—N5	−156.8 (3)
Co—O1—C1—O3	−174.9 (2)	O4—C22—C23—N5	24.5 (4)
Co—O1—C1—O2	4.30 (19)	O4—C22—C23—N5	24.5 (4)
O1—Co—C1—O2	−175.1 (2)	O6—O6—C24—N5	0.0 (2)
N1—Co—C1—O2	94.21 (14)	O6—O6—C24—C25	0.0 (3)
N4—Co—C1—O2	−84.86 (14)	C23—N5—C24—O6	9.6 (4)
N2—Co—C1—O2	174.41 (13)	C23—N5—C24—O6	9.6 (4)
N3—Co—C1—O2	−0.40 (19)	C23—N5—C24—C25	−169.8 (3)
O2—Co—C1—O1	175.1 (2)	O6—C24—C25—C27	165.5 (3)
N1—Co—C1—O1	−90.72 (14)	O6—C24—C25—C27	165.5 (3)
N4—Co—C1—O1	90.21 (14)	N5—C24—C25—C27	−15.1 (4)
N2—Co—C1—O1	−10.53 (18)	O6—C24—C25—C26	−14.2 (4)
N3—Co—C1—O1	174.67 (13)	O6—C24—C25—C26	−14.2 (4)
C6—N1—C2—C3	1.9 (4)	N5—C24—C25—C26	165.1 (2)
Co—N1—C2—C3	−176.7 (2)	C27—C25—C26—C27i	0.5 (4)
N1—C2—C3—C4	−2.4 (4)	C24—C25—C26—C27i	−179.8 (2)
C2—C3—C4—C5	1.3 (5)	C26—C25—C27—C26i	−0.5 (4)
C3—C4—C5—C6	0.2 (4)	C24—C25—C27—C26i	179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O6	0.85 (6)	2.11 (6)	2.944 (5)	168 (5)
O7—H7B···O9	0.79 (7)	2.02 (7)	2.805 (5)	170 (6)
O8—H8A···O5	0.79 (5)	1.94 (5)	2.722 (4)	170 (5)
O9—H9A···O4ii	0.86 (5)	1.98 (6)	2.831 (4)	170 (4)
O9—H9B···O4	0.76 (5)	2.07 (5)	2.812 (4)	165 (5)
N5—H5A···O8iii	0.74 (4)	2.16 (4)	2.881 (4)	163 (3)
C3—H3···O4iv	0.94 (3)	2.64 (3)	3.203 (4)	119 (2)
C15—H15···O5	0.96 (4)	2.32 (4)	3.264 (4)	165 (3)
C20—H20···O6v	0.90 (4)	2.46 (4)	3.162 (4)	135 (3)
C14—H14···Cg2vi	0.86 (4)	2.59 (3)	3.419 (3)	160 (3)

D—H···Cg	D—H	H···Cg	D—H···Cg	D—H···Cg
C14viii—H14viii···Cg2	0.86 (4)	2.59 (3)	3.4191 (34)	160 (3)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the N2/C7–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O6	0.85 (6)	2.11 (6)	2.944 (5)	168 (5)
O7—H7B⋯O9	0.79 (7)	2.02 (7)	2.805 (5)	170 (6)
O8—H8A⋯O5	0.79 (5)	1.94 (5)	2.722 (4)	170 (5)
O9—H9A⋯O4i	0.86 (5)	1.98 (6)	2.831 (4)	170 (4)
O9—H9B⋯O4	0.76 (5)	2.07 (5)	2.812 (4)	165 (5)
N5—H5A⋯O8ii	0.74 (4)	2.16 (4)	2.881 (4)	163 (3)
C3—H3⋯O4iii	0.94 (3)	2.64 (3)	3.203 (4)	119 (2)
C15—H15⋯O5	0.96 (4)	2.32 (4)	3.264 (4)	165 (3)
C20—H20⋯O6iv	0.90 (4)	2.46 (4)	3.162 (4)	135 (3)
C14—H14⋯Cg2v	0.86 (4)	2.59 (3)	3.419 (3)	160 (3)

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