Phenyl-hydrazinium (6-carb-oxy-pyridine-2-carboxyl-ato)(pyridine-2,6-dicarboxyl-ato)cobaltate(II)-pyridine-2,6-dicarb-oxy-lic acid-water (1/1/3).

The asymmetric unit of the title compound, (C(6)H(9)N(2))[Co(C(7)H(3)NO(4))(C(7)H(4)NO(4))]·C(7)H(5)NO(4)·3H(2)O, contains one (6-carb-oxy-pyridine-2-carboxyl-ato)(pyridine-2,6-dicarboxyl-ato)cobaltate(II) anion, one phenyl-hydrazinium cation, one pyridine-2,6-dicarb-oxy-lic acid mol-ecule and three uncoordin-ated water mol-ecules, part of which are disordered. The Co(II) ion is coordinated by a pyridine-2,6-dicarboxyl-ate ion and a 6-carb-oxy-pyridine-2-carboxyl-ate ligand almost perpendicular to each other [the angle between the least-squares planes is 87.38 (4)°] and is surrounded by two O atoms and two N atoms in the equatorial plane and two O atoms in axial positions, resulting in a distorted octa-hedral coordination geometry. There is an extensive three-dimensional network of O-H⋯O and N-H⋯O hydrogen bonds, which link the components.

Related literature

For related cobalt, copper and cadmium complexes containing 2,6-dicarboxyl­ato ligands, see: Aghabozorg et al. (2008 ▶); Aghabozorg et al. (2009 ▶); Moghimi et al. (2002 ▶). For an isotypic series of five related M(II) complexes, see: MacDonald et al. (2004 ▶). For the supra­molecular chemistry and crystal structures of five bis­(imidazolium 2,6-pyridine­dicarboxyl­ate)M(II) complexes, see: MacDonald et al. (2000 ▶).

Experimental

Crystal data

(C6H9N2)[Co(C7H3NO4)(C7H4NO4)]·C7H5NO4·3H2O

M = 720.47

Triclinic,

a = 8.8019 (4) Å

b = 12.2378 (5) Å

c = 14.6559 (7) Å

α = 101.080 (2)°

β = 91.351 (3)°

γ = 98.749 (3)°

V = 1528.95 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.64 mm−1

T = 293 K

0.25 × 0.12 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.825, T max = 0.999

27004 measured reflections

5526 independent reflections

4198 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.167

S = 1.13

5526 reflections

462 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.71 e Å−3

Δρmin = −0.78 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048191/si2309sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048191/si2309Isup2.hkl

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

(C6H9N2)[Co(C7H3NO4)(C7H4NO4)]·C7H5NO4·3H2O	Z = 2
Mr = 720.47	F(000) = 742
Triclinic, P1	Dx = 1.565 Mg m−3
a = 8.8019 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2378 (5) Å	Cell parameters from 8005 reflections
c = 14.6559 (7) Å	θ = 2.8–25.2°
α = 101.080 (2)°	µ = 0.64 mm−1
β = 91.351 (3)°	T = 293 K
γ = 98.749 (3)°	Block, brown
V = 1528.95 (12) Å3	0.25 × 0.12 × 0.12 mm

Bruker APEX CCD area-detector diffractometer	5526 independent reflections
Radiation source: fine-focus sealed tube	4198 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→10
Tmin = 0.825, Tmax = 0.999	k = −14→14
27004 measured reflections	l = −17→17

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) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.1037P)2] where P = (Fo2 + 2Fc2)/3
5526 reflections	(Δ/σ)max = 0.002
462 parameters	Δρmax = 0.71 e Å−3
6 restraints	Δρmin = −0.78 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.08241 (5)	0.11526 (3)	0.27416 (3)	0.03986 (15)
N1	0.0353 (3)	0.20143 (19)	0.17546 (17)	0.0321 (5)
N2	0.1315 (3)	0.0232 (2)	0.36950 (16)	0.0333 (6)
O1	0.1988 (3)	0.04183 (18)	0.15618 (15)	0.0439 (5)
O2	0.2202 (3)	0.03896 (18)	0.00472 (16)	0.0467 (6)
O3	−0.0290 (3)	0.2509 (2)	0.34757 (17)	0.0604 (7)
O4	−0.1504 (3)	0.3913 (2)	0.32449 (19)	0.0718 (8)
O5	−0.1078 (3)	−0.0133 (2)	0.25722 (17)	0.0549 (6)
O6	−0.2095 (3)	−0.1669 (2)	0.30695 (18)	0.0554 (6)
O7	0.3082 (3)	0.2062 (2)	0.35125 (17)	0.0533 (6)
O8	0.4774 (3)	0.1909 (2)	0.46295 (19)	0.0645 (7)
H8	0.5193	0.2522	0.4538	0.097*
O13	0.7224 (4)	0.5896 (2)	0.2939 (2)	0.0735 (8)
H13A	0.767 (4)	0.6505 (12)	0.328 (2)	0.110*
H13B	0.765 (3)	0.5383 (15)	0.310 (3)	0.110*
O14	0.6225 (4)	0.3733 (3)	0.4384 (2)	0.0911 (10)
H14A	0.696 (2)	0.384 (3)	0.4033 (16)	0.137*
H14B	0.606 (4)	0.4388 (13)	0.464 (3)	0.137*
O15	0.7032 (9)	0.5579 (4)	0.5692 (4)	0.111 (3)	0.600 (6)
O16	0.0711 (12)	0.3917 (6)	0.5180 (5)	0.100 (4)	0.400 (6)
C1	0.1723 (3)	0.0746 (2)	0.0823 (2)	0.0344 (7)
C2	0.0767 (3)	0.1683 (2)	0.0894 (2)	0.0315 (6)
C3	0.0373 (4)	0.2194 (3)	0.0181 (2)	0.0388 (7)
H3	0.0651	0.1947	−0.0424	0.047*
C4	−0.0448 (4)	0.3087 (3)	0.0388 (2)	0.0430 (8)
H4	−0.0725	0.3448	−0.0079	0.052*
C5	−0.0851 (4)	0.3435 (3)	0.1288 (2)	0.0437 (8)
H5	−0.1393	0.4035	0.1437	0.052*
C6	−0.0434 (3)	0.2873 (2)	0.1966 (2)	0.0355 (7)
C7	−0.0777 (4)	0.3123 (3)	0.2975 (2)	0.0472 (8)
C8	−0.1070 (4)	−0.0855 (3)	0.3071 (2)	0.0413 (8)
C9	0.0315 (3)	−0.0679 (2)	0.3749 (2)	0.0357 (7)
C10	0.0559 (4)	−0.1344 (3)	0.4379 (2)	0.0417 (8)
H10	−0.0138	−0.1988	0.4404	0.050*
C11	0.1854 (4)	−0.1037 (3)	0.4969 (2)	0.0465 (8)
H11	0.2037	−0.1474	0.5401	0.056*
C12	0.2878 (4)	−0.0085 (3)	0.4920 (2)	0.0438 (8)
H12	0.3755	0.0137	0.5318	0.053*
C13	0.2571 (3)	0.0526 (3)	0.4267 (2)	0.0388 (7)
C14	0.3519 (4)	0.1574 (3)	0.4096 (2)	0.0441 (8)
N3	0.5452 (3)	0.71742 (19)	0.98841 (17)	0.0336 (6)
O9	0.3803 (3)	0.88505 (18)	1.00552 (14)	0.0423 (5)
H9	0.3352	0.9391	1.0061	0.063*
O10	0.3851 (3)	0.88449 (19)	0.85355 (16)	0.0494 (6)
O11	0.6360 (3)	0.6510 (2)	1.14056 (17)	0.0620 (7)
H11A	0.6807	0.6353	1.1849	0.093*
O12	0.7558 (3)	0.5215 (2)	1.0602 (2)	0.0749 (8)
C16	0.4987 (3)	0.7465 (2)	0.9112 (2)	0.0354 (7)
C17	0.5231 (4)	0.6919 (3)	0.8224 (2)	0.0458 (8)
H17	0.4890	0.7164	0.7704	0.055*
C18	0.5987 (4)	0.6008 (3)	0.8129 (3)	0.0550 (9)
H18	0.6161	0.5617	0.7541	0.066*
C19	0.6486 (4)	0.5682 (3)	0.8917 (3)	0.0475 (8)
H19	0.7006	0.5068	0.8872	0.057*
C20	0.6203 (3)	0.6280 (2)	0.9773 (2)	0.0378 (7)
C15	0.4154 (3)	0.8466 (2)	0.9206 (2)	0.0353 (7)
C21	0.6782 (4)	0.5948 (3)	1.0634 (3)	0.0456 (8)
N4	0.5745 (3)	0.8905 (2)	0.17482 (17)	0.0379 (6)
H4A	0.6351	0.8616	0.2101	0.057*
H4B	0.6256	0.9537	0.1619	0.057*
H4C	0.5459	0.8410	0.1221	0.057*
N5	0.4388 (3)	0.9152 (2)	0.22451 (19)	0.0416 (6)
H5A	0.373 (4)	0.950 (3)	0.186 (2)	0.050*
C22	0.3461 (4)	0.8152 (2)	0.2400 (2)	0.0367 (7)
C23	0.1992 (4)	0.7818 (3)	0.1991 (2)	0.0488 (9)
H23	0.1624	0.8224	0.1582	0.059*
C24	0.1081 (4)	0.6894 (3)	0.2185 (3)	0.0580 (10)
H24	0.0091	0.6677	0.1910	0.070*
C25	0.1611 (5)	0.6277 (3)	0.2787 (3)	0.0599 (11)
H25	0.0990	0.5644	0.2913	0.072*
C26	0.3070 (5)	0.6615 (3)	0.3196 (3)	0.0566 (10)
H26	0.3432	0.6208	0.3606	0.068*
C27	0.4004 (4)	0.7545 (3)	0.3010 (2)	0.0483 (8)
H27	0.4991	0.7765	0.3290	0.058*

	U11	U22	U33	U12	U13	U23
Co1	0.0464 (3)	0.0381 (2)	0.0397 (3)	0.0132 (2)	0.0000 (2)	0.01435 (19)
N1	0.0308 (12)	0.0296 (12)	0.0389 (14)	0.0099 (10)	0.0025 (11)	0.0103 (10)
N2	0.0325 (13)	0.0362 (13)	0.0320 (13)	0.0088 (11)	0.0009 (11)	0.0062 (10)
O1	0.0504 (13)	0.0434 (12)	0.0459 (13)	0.0248 (10)	0.0005 (10)	0.0152 (10)
O2	0.0571 (14)	0.0433 (12)	0.0446 (13)	0.0251 (11)	0.0051 (11)	0.0068 (10)
O3	0.0909 (19)	0.0574 (15)	0.0440 (14)	0.0353 (14)	0.0181 (13)	0.0174 (12)
O4	0.104 (2)	0.0577 (15)	0.0709 (18)	0.0476 (15)	0.0441 (16)	0.0228 (13)
O5	0.0472 (14)	0.0600 (15)	0.0607 (15)	0.0037 (12)	−0.0168 (12)	0.0258 (13)
O6	0.0474 (14)	0.0505 (14)	0.0652 (16)	−0.0032 (12)	−0.0096 (12)	0.0138 (12)
O7	0.0584 (15)	0.0524 (14)	0.0492 (14)	−0.0025 (12)	−0.0069 (12)	0.0202 (12)
O8	0.0483 (15)	0.0739 (19)	0.0680 (17)	−0.0122 (13)	−0.0157 (13)	0.0254 (15)
O13	0.090 (2)	0.0642 (17)	0.0686 (19)	0.0135 (16)	−0.0180 (16)	0.0220 (15)
O14	0.097 (2)	0.076 (2)	0.088 (2)	−0.0165 (18)	0.0360 (19)	0.0076 (18)
O15	0.196 (7)	0.056 (3)	0.082 (4)	0.050 (4)	−0.017 (4)	−0.006 (3)
O16	0.175 (9)	0.061 (5)	0.050 (5)	−0.001 (5)	−0.032 (5)	−0.002 (4)
C1	0.0299 (15)	0.0291 (15)	0.0440 (18)	0.0072 (12)	−0.0010 (13)	0.0050 (13)
C2	0.0296 (14)	0.0272 (14)	0.0377 (17)	0.0064 (12)	−0.0018 (12)	0.0055 (12)
C3	0.0424 (17)	0.0395 (17)	0.0370 (17)	0.0112 (14)	0.0000 (14)	0.0102 (14)
C4	0.0484 (19)	0.0414 (17)	0.0454 (19)	0.0167 (15)	−0.0020 (15)	0.0170 (15)
C5	0.0425 (18)	0.0367 (16)	0.058 (2)	0.0165 (14)	0.0052 (16)	0.0165 (15)
C6	0.0357 (16)	0.0267 (14)	0.0470 (18)	0.0088 (12)	0.0075 (14)	0.0111 (13)
C7	0.057 (2)	0.0402 (18)	0.050 (2)	0.0163 (16)	0.0156 (17)	0.0155 (15)
C8	0.0385 (17)	0.0402 (18)	0.0445 (19)	0.0089 (15)	−0.0032 (14)	0.0055 (15)
C9	0.0366 (16)	0.0356 (16)	0.0352 (16)	0.0121 (13)	0.0035 (13)	0.0028 (13)
C10	0.0446 (18)	0.0393 (17)	0.0446 (19)	0.0113 (14)	0.0047 (15)	0.0126 (14)
C11	0.0488 (19)	0.053 (2)	0.0465 (19)	0.0175 (16)	0.0058 (16)	0.0241 (16)
C12	0.0386 (17)	0.062 (2)	0.0354 (17)	0.0181 (16)	−0.0019 (14)	0.0139 (15)
C13	0.0322 (16)	0.0497 (18)	0.0360 (17)	0.0120 (14)	0.0028 (13)	0.0081 (14)
C14	0.0376 (18)	0.052 (2)	0.0418 (19)	0.0032 (15)	0.0008 (15)	0.0095 (16)
N3	0.0318 (13)	0.0267 (12)	0.0436 (15)	0.0073 (10)	0.0022 (11)	0.0081 (10)
O9	0.0508 (13)	0.0435 (12)	0.0390 (12)	0.0241 (10)	0.0050 (10)	0.0109 (10)
O10	0.0688 (16)	0.0441 (13)	0.0418 (13)	0.0214 (12)	0.0017 (11)	0.0150 (10)
O11	0.0911 (19)	0.0541 (14)	0.0491 (15)	0.0348 (14)	−0.0068 (14)	0.0137 (12)
O12	0.090 (2)	0.0721 (17)	0.083 (2)	0.0550 (16)	0.0105 (16)	0.0316 (15)
C16	0.0360 (16)	0.0297 (15)	0.0401 (17)	0.0055 (13)	0.0023 (13)	0.0058 (13)
C17	0.053 (2)	0.0431 (18)	0.0412 (19)	0.0128 (16)	0.0045 (16)	0.0041 (15)
C18	0.065 (2)	0.049 (2)	0.049 (2)	0.0212 (18)	0.0111 (18)	−0.0050 (17)
C19	0.0490 (19)	0.0331 (16)	0.060 (2)	0.0140 (15)	0.0082 (17)	0.0027 (15)
C20	0.0343 (16)	0.0282 (15)	0.0509 (19)	0.0073 (13)	0.0026 (14)	0.0063 (13)
C15	0.0331 (16)	0.0316 (15)	0.0415 (18)	0.0046 (13)	0.0010 (13)	0.0085 (13)
C21	0.0457 (19)	0.0328 (16)	0.062 (2)	0.0110 (15)	0.0006 (16)	0.0145 (15)
N4	0.0375 (14)	0.0356 (13)	0.0411 (15)	0.0069 (11)	−0.0027 (11)	0.0089 (11)
N5	0.0447 (15)	0.0362 (14)	0.0466 (16)	0.0124 (12)	0.0043 (13)	0.0095 (12)
C22	0.0430 (17)	0.0337 (16)	0.0337 (16)	0.0103 (14)	0.0060 (14)	0.0032 (13)
C23	0.048 (2)	0.049 (2)	0.048 (2)	0.0101 (17)	−0.0021 (16)	0.0062 (16)
C24	0.048 (2)	0.056 (2)	0.065 (3)	0.0004 (18)	0.0050 (18)	0.0026 (19)
C25	0.072 (3)	0.041 (2)	0.061 (2)	−0.0036 (19)	0.025 (2)	0.0023 (18)
C26	0.081 (3)	0.046 (2)	0.046 (2)	0.014 (2)	0.0116 (19)	0.0153 (16)
C27	0.055 (2)	0.049 (2)	0.0430 (19)	0.0095 (17)	−0.0043 (16)	0.0129 (16)

Co1—N1	2.017 (2)	C12—C13	1.368 (4)
Co1—N2	2.033 (2)	C12—H12	0.9300
Co1—O5	2.090 (2)	C13—C14	1.487 (5)
Co1—O1	2.148 (2)	N3—C16	1.323 (4)
Co1—O3	2.175 (2)	N3—C20	1.348 (3)
Co1—O7	2.281 (2)	O9—C15	1.304 (4)
N1—C2	1.325 (4)	O9—H9	0.8200
N1—C6	1.337 (3)	O10—C15	1.206 (4)
N2—C9	1.327 (4)	O11—C21	1.300 (4)
N2—C13	1.332 (4)	O11—H11A	0.8200
O1—C1	1.254 (4)	O12—C21	1.202 (4)
O2—C1	1.244 (4)	C16—C17	1.382 (4)
O3—C7	1.257 (4)	C16—C15	1.507 (4)
O4—C7	1.247 (4)	C17—C18	1.369 (4)
O5—C8	1.251 (4)	C17—H17	0.9300
O6—C8	1.238 (4)	C18—C19	1.376 (5)
O7—C14	1.219 (4)	C18—H18	0.9300
O8—C14	1.303 (4)	C19—C20	1.375 (4)
O8—H8	0.8200	C19—H19	0.9300
O13—H13A	0.85 (2)	C20—C21	1.498 (4)
O13—H13B	0.85 (3)	N4—N5	1.454 (3)
O14—H14A	0.85 (2)	N4—H4A	0.8900
O14—H14B	0.85 (3)	N4—H4B	0.8900
C1—C2	1.512 (4)	N4—H4C	0.8900
C2—C3	1.380 (4)	N5—C22	1.424 (4)
C3—C4	1.390 (4)	N5—H5A	0.99 (3)
C3—H3	0.9300	C22—C23	1.380 (5)
C4—C5	1.377 (5)	C22—C27	1.386 (4)
C4—H4	0.9300	C23—C24	1.365 (5)
C5—C6	1.385 (4)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.382 (5)
C6—C7	1.500 (4)	C24—H24	0.9300
C8—C9	1.517 (4)	C25—C26	1.373 (6)
C9—C10	1.375 (4)	C25—H25	0.9300
C10—C11	1.373 (5)	C26—C27	1.376 (5)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.376 (5)	C27—H27	0.9300
C11—H11	0.9300
N1—Co1—N2	177.68 (9)	C13—C12—C11	118.1 (3)
N1—Co1—O5	102.10 (9)	C13—C12—H12	121.0
N2—Co1—O5	77.14 (9)	C11—C12—H12	121.0
N1—Co1—O1	76.28 (8)	N2—C13—C12	122.1 (3)
N2—Co1—O1	101.57 (8)	N2—C13—C14	111.1 (3)
O5—Co1—O1	96.18 (10)	C12—C13—C14	126.8 (3)
N1—Co1—O3	75.72 (9)	O7—C14—O8	125.3 (3)
N2—Co1—O3	106.53 (9)	O7—C14—C13	120.2 (3)
O5—Co1—O3	97.68 (10)	O8—C14—C13	114.5 (3)
O1—Co1—O3	150.78 (9)	C16—N3—C20	116.3 (3)
N1—Co1—O7	107.38 (9)	C15—O9—H9	109.5
N2—Co1—O7	73.46 (9)	C21—O11—H11A	109.5
O5—Co1—O7	150.47 (9)	N3—C16—C17	124.3 (3)
O1—Co1—O7	92.35 (9)	N3—C16—C15	118.0 (3)
O3—Co1—O7	88.12 (10)	C17—C16—C15	117.7 (3)
C2—N1—C6	121.0 (2)	C18—C17—C16	118.3 (3)
C2—N1—Co1	119.22 (18)	C18—C17—H17	120.8
C6—N1—Co1	119.7 (2)	C16—C17—H17	120.8
C9—N2—C13	119.9 (3)	C17—C18—C19	118.9 (3)
C9—N2—Co1	117.7 (2)	C17—C18—H18	120.5
C13—N2—Co1	122.4 (2)	C19—C18—H18	120.5
C1—O1—Co1	115.10 (17)	C20—C19—C18	118.8 (3)
C7—O3—Co1	115.3 (2)	C20—C19—H19	120.6
C8—O5—Co1	116.8 (2)	C18—C19—H19	120.6
C14—O7—Co1	112.8 (2)	N3—C20—C19	123.3 (3)
C14—O8—H8	109.5	N3—C20—C21	117.7 (3)
H13A—O13—H13B	105 (3)	C19—C20—C21	119.0 (3)
H14A—O14—H14B	105 (3)	O10—C15—O9	125.0 (3)
O2—C1—O1	126.1 (3)	O10—C15—C16	120.9 (3)
O2—C1—C2	117.5 (3)	O9—C15—C16	114.1 (3)
O1—C1—C2	116.4 (3)	O12—C21—O11	123.5 (3)
N1—C2—C3	121.4 (3)	O12—C21—C20	122.3 (3)
N1—C2—C1	112.3 (2)	O11—C21—C20	114.2 (3)
C3—C2—C1	126.4 (3)	N5—N4—H4A	109.5
C2—C3—C4	118.3 (3)	N5—N4—H4B	109.5
C2—C3—H3	120.9	H4A—N4—H4B	109.5
C4—C3—H3	120.9	N5—N4—H4C	109.5
C5—C4—C3	119.8 (3)	H4A—N4—H4C	109.5
C5—C4—H4	120.1	H4B—N4—H4C	109.5
C3—C4—H4	120.1	C22—N5—N4	111.7 (2)
C4—C5—C6	118.7 (3)	C22—N5—H5A	106 (2)
C4—C5—H5	120.7	N4—N5—H5A	109.6 (19)
C6—C5—H5	120.7	C23—C22—C27	119.7 (3)
N1—C6—C5	120.8 (3)	C23—C22—N5	120.5 (3)
N1—C6—C7	112.8 (2)	C27—C22—N5	119.6 (3)
C5—C6—C7	126.4 (3)	C24—C23—C22	120.1 (3)
O4—C7—O3	125.9 (3)	C24—C23—H23	120.0
O4—C7—C6	117.9 (3)	C22—C23—H23	120.0
O3—C7—C6	116.2 (3)	C23—C24—C25	120.8 (4)
O6—C8—O5	125.9 (3)	C23—C24—H24	119.6
O6—C8—C9	118.3 (3)	C25—C24—H24	119.6
O5—C8—C9	115.8 (3)	C26—C25—C24	118.9 (4)
N2—C9—C10	121.3 (3)	C26—C25—H25	120.5
N2—C9—C8	112.5 (3)	C24—C25—H25	120.5
C10—C9—C8	126.2 (3)	C25—C26—C27	121.1 (4)
C11—C10—C9	118.7 (3)	C25—C26—H26	119.4
C11—C10—H10	120.7	C27—C26—H26	119.4
C9—C10—H10	120.7	C26—C27—C22	119.3 (3)
C10—C11—C12	120.0 (3)	C26—C27—H27	120.3
C10—C11—H11	120.0	C22—C27—H27	120.3
C12—C11—H11	120.0
N2—Co1—N1—C2	−15 (2)	Co1—O3—C7—O4	176.8 (3)
O5—Co1—N1—C2	−86.1 (2)	Co1—O3—C7—C6	−3.6 (4)
O1—Co1—N1—C2	7.4 (2)	N1—C6—C7—O4	179.8 (3)
O3—Co1—N1—C2	178.9 (2)	C5—C6—C7—O4	−0.3 (5)
O7—Co1—N1—C2	95.6 (2)	N1—C6—C7—O3	0.1 (4)
N2—Co1—N1—C6	161 (2)	C5—C6—C7—O3	−180.0 (3)
O5—Co1—N1—C6	90.7 (2)	Co1—O5—C8—O6	179.7 (3)
O1—Co1—N1—C6	−175.8 (2)	Co1—O5—C8—C9	1.3 (4)
O3—Co1—N1—C6	−4.3 (2)	C13—N2—C9—C10	−1.0 (4)
O7—Co1—N1—C6	−87.7 (2)	Co1—N2—C9—C10	−179.7 (2)
N1—Co1—N2—C9	−70 (2)	C13—N2—C9—C8	177.8 (2)
O5—Co1—N2—C9	1.2 (2)	Co1—N2—C9—C8	−0.9 (3)
O1—Co1—N2—C9	−92.6 (2)	O6—C8—C9—N2	−178.8 (3)
O3—Co1—N2—C9	95.5 (2)	O5—C8—C9—N2	−0.3 (4)
O7—Co1—N2—C9	178.4 (2)	O6—C8—C9—C10	−0.1 (5)
N1—Co1—N2—C13	111 (2)	O5—C8—C9—C10	178.4 (3)
O5—Co1—N2—C13	−177.5 (2)	N2—C9—C10—C11	1.1 (5)
O1—Co1—N2—C13	88.8 (2)	C8—C9—C10—C11	−177.5 (3)
O3—Co1—N2—C13	−83.1 (2)	C9—C10—C11—C12	−0.3 (5)
O7—Co1—N2—C13	−0.3 (2)	C10—C11—C12—C13	−0.6 (5)
N1—Co1—O1—C1	−7.2 (2)	C9—N2—C13—C12	0.0 (4)
N2—Co1—O1—C1	171.9 (2)	Co1—N2—C13—C12	178.7 (2)
O5—Co1—O1—C1	93.8 (2)	C9—N2—C13—C14	−179.4 (2)
O3—Co1—O1—C1	−24.1 (3)	Co1—N2—C13—C14	−0.7 (3)
O7—Co1—O1—C1	−114.5 (2)	C11—C12—C13—N2	0.8 (5)
N1—Co1—O3—C7	4.2 (3)	C11—C12—C13—C14	−179.9 (3)
N2—Co1—O3—C7	−175.2 (3)	Co1—O7—C14—O8	179.7 (3)
O5—Co1—O3—C7	−96.4 (3)	Co1—O7—C14—C13	−2.4 (4)
O1—Co1—O3—C7	21.3 (4)	N2—C13—C14—O7	2.2 (4)
O7—Co1—O3—C7	112.7 (3)	C12—C13—C14—O7	−177.2 (3)
N1—Co1—O5—C8	176.4 (2)	N2—C13—C14—O8	−179.7 (3)
N2—Co1—O5—C8	−1.4 (2)	C12—C13—C14—O8	0.9 (5)
O1—Co1—O5—C8	99.1 (2)	C20—N3—C16—C17	−0.4 (4)
O3—Co1—O5—C8	−106.7 (2)	C20—N3—C16—C15	−179.5 (3)
O7—Co1—O5—C8	−6.8 (4)	N3—C16—C17—C18	0.8 (5)
N1—Co1—O7—C14	−176.3 (2)	C15—C16—C17—C18	179.9 (3)
N2—Co1—O7—C14	1.4 (2)	C16—C17—C18—C19	−0.7 (5)
O5—Co1—O7—C14	7.0 (4)	C17—C18—C19—C20	0.2 (5)
O1—Co1—O7—C14	−99.9 (2)	C16—N3—C20—C19	−0.1 (5)
O3—Co1—O7—C14	109.3 (2)	C16—N3—C20—C21	178.4 (3)
Co1—O1—C1—O2	−175.8 (2)	C18—C19—C20—N3	0.2 (5)
Co1—O1—C1—C2	6.0 (3)	C18—C19—C20—C21	−178.3 (3)
C6—N1—C2—C3	−1.4 (4)	N3—C16—C15—O10	171.8 (3)
Co1—N1—C2—C3	175.3 (2)	C17—C16—C15—O10	−7.3 (5)
C6—N1—C2—C1	176.7 (3)	N3—C16—C15—O9	−8.7 (4)
Co1—N1—C2—C1	−6.6 (3)	C17—C16—C15—O9	172.1 (3)
O2—C1—C2—N1	−178.4 (3)	N3—C20—C21—O12	−174.5 (3)
O1—C1—C2—N1	0.0 (4)	C19—C20—C21—O12	4.1 (5)
O2—C1—C2—C3	−0.4 (5)	N3—C20—C21—O11	6.2 (4)
O1—C1—C2—C3	178.0 (3)	C19—C20—C21—O11	−175.2 (3)
N1—C2—C3—C4	1.2 (5)	N4—N5—C22—C23	−115.4 (3)
C1—C2—C3—C4	−176.6 (3)	N4—N5—C22—C27	68.4 (4)
C2—C3—C4—C5	−0.2 (5)	C27—C22—C23—C24	−0.1 (5)
C3—C4—C5—C6	−0.6 (5)	N5—C22—C23—C24	−176.3 (3)
C2—N1—C6—C5	0.6 (4)	C22—C23—C24—C25	−0.3 (5)
Co1—N1—C6—C5	−176.1 (2)	C23—C24—C25—C26	0.7 (6)
C2—N1—C6—C7	−179.5 (3)	C24—C25—C26—C27	−0.5 (5)
Co1—N1—C6—C7	3.8 (3)	C25—C26—C27—C22	0.1 (5)
C4—C5—C6—N1	0.4 (5)	C23—C22—C27—C26	0.2 (5)
C4—C5—C6—C7	−179.5 (3)	N5—C22—C27—C26	176.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O14	0.82	1.67	2.491 (4)	174
O13—H13A···O6i	0.85 (2)	2.29 (2)	2.917 (4)	131 (3)
O13—H13B···O4ii	0.85 (3)	2.09 (2)	2.926 (4)	168 (3)
O14—H14A···O4ii	0.85 (2)	1.80 (2)	2.645 (4)	174 (3)
O14—H14B···O15	0.85 (3)	1.98 (4)	2.658 (6)	136 (4)
O9—H9···O2iii	0.82	1.70	2.520 (3)	173
O11—H11A···O13iv	0.82	1.84	2.634 (4)	163
N4—H4A···O6i	0.89	2.06	2.935 (3)	167
N4—H4A···O5i	0.89	2.53	2.993 (3)	113
N4—H4A···O11v	0.89	2.58	3.011 (3)	110
N4—H4B···O10vi	0.89	2.05	2.834 (3)	146
N4—H4C···O9v	0.89	2.41	2.964 (3)	121
N5—H5A···O1vii	0.99 (3)	2.12 (3)	3.060 (3)	158 (3)

Table 1

Selected bond lengths (Å)

Co1—N1	2.017 (2)
Co1—N2	2.033 (2)
Co1—O5	2.090 (2)
Co1—O1	2.148 (2)
Co1—O3	2.175 (2)
Co1—O7	2.281 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O14	0.82	1.67	2.491 (4)	174
O13—H13A⋯O6i	0.85 (2)	2.29 (2)	2.917 (4)	131 (3)
O13—H13B⋯O4ii	0.85 (3)	2.09 (2)	2.926 (4)	168 (3)
O14—H14A⋯O4ii	0.85 (2)	1.80 (2)	2.645 (4)	174 (3)
O14—H14B⋯O15	0.85 (3)	1.98 (4)	2.658 (6)	136 (4)
O9—H9⋯O2iii	0.82	1.70	2.520 (3)	173
O11—H11A⋯O13iv	0.82	1.84	2.634 (4)	163
N4—H4A⋯O6i	0.89	2.06	2.935 (3)	167
N4—H4A⋯O5i	0.89	2.53	2.993 (3)	113
N4—H4A⋯O11v	0.89	2.58	3.011 (3)	110
N4—H4B⋯O10vi	0.89	2.05	2.834 (3)	146
N4—H4C⋯O9v	0.89	2.41	2.964 (3)	121
N5—H5A⋯O1vii	0.99 (3)	2.12 (3)	3.060 (3)	158 (3)

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