Bis[tetra-aqua-(1,10-phenanthroline-κN,N')cobalt(II)] hexa-aqua-cobalt(II) bis-[3,5-bis-(carboxyl-atometh-oxy)benzoate] tetra-hydrate.

The title compound, [Co(C(12)H(8)N(2))(H(2)O)(4)](2)[Co(H(2)O)(6)](C(11)H(7)O(8))(2)·4H(2)O, was obtanied by the reaction of cobalt acetate with 3,5-bis-(carb-oxy-meth-oxy)benzoic acid and 1,10-phenanthroline. The asymmetric unit contains one tetra-aqua-(1,10-phenanthroline)cobalt(II) cation, one half of a hexa-aqua-cobalt(II) cation that is completed by inversion symmetry, one 3,5-bis-(carboxyl-atometh-oxy)benzoate trianion and two lattice water mol-ecules. The two Co(II) atoms each show a slightly distorted octa-hedral coordination (CoO(6) and CoO(4)N(2)). The cations, anions and lattice water mol-ecules are linked by an intricate network of O-H⋯O hydrogen bonds into a three-dimensional structure.

Related literature

For background to multicarboxyl­ate ligands, see: Cao et al. (2002 ▶); Dai et al. (2002 ▶); He et al. (2008 ▶); Rowsell et al. (2005 ▶); Wang et al. (2005 ▶).

Experimental

Crystal data

[Co(C12H8N2)(H2O)4]2[Co(H2O)6](C11H7O8)2·4H2O

M = 1395.82

Monoclinic,

a = 7.0924 (1) Å

b = 20.3779 (4) Å

c = 20.1810 (3) Å

β = 99.063 (1)°

V = 2880.31 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.96 mm−1

T = 296 K

0.22 × 0.15 × 0.07 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.839, T max = 0.933

21923 measured reflections

5080 independent reflections

3751 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.09

5080 reflections

450 parameters

27 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046386/wm2426sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046386/wm2426Isup2.hkl

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

[Co(C12H8N2)(H2O)4]2[Co(H2O)6](C11H7O8)2·4H2O	F(000) = 1446
Mr = 1395.82	Dx = 1.609 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3158 reflections
a = 7.0924 (1) Å	θ = 1.4–25.0°
b = 20.3779 (4) Å	µ = 0.96 mm−1
c = 20.1810 (3) Å	T = 296 K
β = 99.063 (1)°	Block, pink
V = 2880.31 (8) Å3	0.22 × 0.15 × 0.07 mm
Z = 2

Bruker APEXII area-detector diffractometer	5080 independent reflections
Radiation source: fine-focus sealed tube	3751 reflections with I > 2σ(I)
graphite	Rint = 0.054
ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.839, Tmax = 0.933	k = −24→24
21923 measured reflections	l = −23→23

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3
5080 reflections	(Δ/σ)max = 0.001
450 parameters	Δρmax = 0.31 e Å−3
27 restraints	Δρmin = −0.30 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
Co1	0.5000	0.0000	0.5000	0.03353 (17)
Co2	0.74606 (6)	0.243825 (19)	0.763479 (18)	0.03271 (14)
N1	0.7089 (3)	0.34589 (12)	0.74971 (11)	0.0339 (6)
N2	0.7521 (3)	0.25550 (12)	0.65761 (11)	0.0344 (6)
O1W	0.6596 (4)	0.23471 (14)	0.85757 (11)	0.0551 (7)
H1WA	0.696 (4)	0.2535 (16)	0.8930 (12)	0.066*
H1WB	0.548 (3)	0.2210 (18)	0.8584 (16)	0.066*
O1	0.7285 (4)	0.00598 (10)	0.32671 (11)	0.0589 (7)
O2W	0.8488 (3)	0.14848 (11)	0.76823 (11)	0.0441 (6)
H2WA	0.921 (4)	0.1411 (17)	0.8057 (9)	0.053*
H2WB	0.926 (4)	0.1379 (16)	0.7422 (11)	0.053*
O2	0.6887 (3)	0.11208 (10)	0.34103 (9)	0.0383 (5)
O3W	0.4615 (3)	0.21473 (13)	0.72790 (10)	0.0486 (6)
H3WA	0.395 (4)	0.1961 (15)	0.7526 (12)	0.058*
H3WB	0.413 (4)	0.2101 (17)	0.6903 (8)	0.058*
O3	0.7342 (3)	0.20327 (10)	0.11420 (9)	0.0472 (6)
O4	0.7996 (3)	0.32426 (10)	0.08547 (9)	0.0479 (6)
O4W	1.0173 (3)	0.26858 (11)	0.81544 (12)	0.0474 (6)
H4WA	1.106 (4)	0.2421 (12)	0.8289 (16)	0.057*
H4WB	1.072 (4)	0.3051 (9)	0.8180 (16)	0.057*
O5W	0.4188 (4)	0.04985 (11)	0.57696 (12)	0.0663 (8)
H5WA	0.367 (5)	0.0307 (15)	0.6061 (15)	0.080*
H5WB	0.389 (6)	0.0890 (9)	0.5780 (18)	0.080*
O5	0.7541 (3)	0.30672 (10)	−0.02457 (9)	0.0382 (5)
O6W	0.4901 (3)	0.08954 (10)	0.44683 (10)	0.0457 (6)
H6WA	0.533 (4)	0.0971 (15)	0.4139 (12)	0.055*
H6WB	0.420 (4)	0.1186 (13)	0.4560 (15)	0.055*
O6	0.6088 (4)	−0.02370 (11)	0.07416 (10)	0.0524 (6)
O7W	0.7879 (4)	0.02001 (14)	0.54018 (13)	0.0592 (7)
H7WA	0.849 (4)	0.0467 (13)	0.5203 (16)	0.071*
H7WB	0.860 (5)	−0.0126 (12)	0.5454 (18)	0.071*
O7	0.6937 (3)	−0.18124 (10)	0.15287 (10)	0.0434 (5)
O8	0.8981 (3)	−0.10571 (11)	0.12730 (10)	0.0465 (6)
O8W	1.1066 (5)	0.11321 (14)	0.68801 (14)	0.0824 (10)
H8WB	1.097 (6)	0.1260 (18)	0.6478 (12)	0.099*
H8WA	1.137 (6)	0.0734 (10)	0.6857 (19)	0.099*
O9W	0.4790 (4)	0.40818 (12)	−0.04843 (13)	0.0514 (6)
H9WA	0.552 (4)	0.3760 (13)	−0.0411 (14)	0.048 (11)*
H9WB	0.401 (5)	0.3993 (19)	−0.0817 (15)	0.104 (19)*
C1	0.6998 (4)	0.39104 (16)	0.79609 (15)	0.0417 (8)
H1A	0.7074	0.3775	0.8404	0.050*
C2	0.6795 (5)	0.45779 (17)	0.78211 (17)	0.0518 (9)
H2A	0.6779	0.4881	0.8165	0.062*
C3	0.6622 (5)	0.47783 (17)	0.71727 (19)	0.0530 (9)
H3A	0.6446	0.5221	0.7068	0.064*
C4	0.6708 (4)	0.43239 (16)	0.66644 (15)	0.0420 (8)
C5	0.6501 (5)	0.44923 (19)	0.59653 (17)	0.0543 (10)
H5A	0.6294	0.4927	0.5835	0.065*
C6	0.6604 (5)	0.40298 (19)	0.54975 (16)	0.0521 (9)
H6A	0.6444	0.4151	0.5048	0.062*
C7	0.6953 (4)	0.33579 (17)	0.56737 (14)	0.0406 (8)
C8	0.6990 (4)	0.36689 (15)	0.68516 (14)	0.0335 (7)
C9	0.7180 (4)	0.31756 (15)	0.63583 (13)	0.0325 (7)
C10	0.7060 (5)	0.28512 (19)	0.52134 (16)	0.0498 (9)
H10A	0.6904	0.2943	0.4757	0.060*
C11	0.7391 (5)	0.2229 (2)	0.54308 (15)	0.0512 (9)
H11A	0.7459	0.1892	0.5125	0.061*
C12	0.7631 (5)	0.20916 (17)	0.61220 (15)	0.0446 (8)
H12A	0.7876	0.1662	0.6266	0.054*
C13	0.6916 (4)	0.07233 (14)	0.22994 (13)	0.0324 (7)
C14	0.7154 (4)	0.13290 (14)	0.20404 (13)	0.0326 (7)
H14A	0.7379	0.1691	0.2323	0.039*
C15	0.7059 (4)	0.14038 (14)	0.13487 (13)	0.0335 (7)
C16	0.6709 (4)	0.08749 (14)	0.09286 (14)	0.0352 (7)
H16A	0.6637	0.0925	0.0467	0.042*
C17	0.6463 (4)	0.02584 (15)	0.12065 (14)	0.0375 (7)
C18	0.6587 (4)	0.01780 (15)	0.18883 (14)	0.0373 (7)
H18A	0.6453	−0.0235	0.2070	0.045*
C19	0.7032 (4)	0.06265 (15)	0.30421 (13)	0.0364 (7)
C20	0.7191 (4)	0.21662 (14)	0.04494 (12)	0.0303 (7)
H20A	0.5913	0.2064	0.0225	0.036*
H20B	0.8088	0.1896	0.0254	0.036*
C21	0.7619 (4)	0.28832 (14)	0.03547 (13)	0.0301 (7)
C22	0.5633 (5)	−0.08635 (15)	0.09867 (16)	0.0491 (9)
H22A	0.4917	−0.1110	0.0620	0.059*
H22B	0.4811	−0.0801	0.1323	0.059*
C23	0.7349 (5)	−0.12653 (16)	0.12912 (13)	0.0366 (8)

	U11	U22	U33	U12	U13	U23
Co1	0.0424 (4)	0.0287 (3)	0.0329 (3)	0.0087 (3)	0.0163 (3)	0.0036 (2)
Co2	0.0366 (3)	0.0297 (3)	0.0316 (2)	0.00050 (19)	0.00464 (18)	−0.00106 (17)
N1	0.0316 (15)	0.0339 (15)	0.0350 (13)	0.0041 (12)	0.0014 (11)	−0.0024 (11)
N2	0.0332 (16)	0.0364 (16)	0.0336 (13)	−0.0016 (12)	0.0057 (11)	−0.0043 (11)
O1W	0.0514 (16)	0.0808 (19)	0.0353 (12)	−0.0249 (14)	0.0131 (12)	−0.0124 (12)
O1	0.106 (2)	0.0308 (14)	0.0483 (12)	0.0189 (13)	0.0372 (14)	0.0146 (10)
O2W	0.0503 (16)	0.0350 (13)	0.0458 (12)	0.0040 (12)	0.0035 (11)	−0.0021 (11)
O2	0.0557 (15)	0.0302 (12)	0.0309 (10)	0.0071 (10)	0.0126 (10)	0.0033 (9)
O3W	0.0424 (15)	0.0666 (17)	0.0352 (11)	−0.0129 (13)	0.0014 (11)	0.0045 (12)
O3	0.0793 (18)	0.0323 (13)	0.0291 (10)	−0.0105 (12)	0.0054 (11)	0.0057 (9)
O4	0.0784 (17)	0.0317 (13)	0.0357 (11)	−0.0141 (12)	0.0151 (11)	−0.0048 (10)
O4W	0.0341 (14)	0.0287 (13)	0.0752 (16)	−0.0024 (11)	−0.0048 (12)	0.0041 (12)
O5W	0.120 (2)	0.0343 (14)	0.0587 (14)	0.0220 (15)	0.0592 (15)	0.0090 (12)
O5	0.0533 (14)	0.0325 (12)	0.0288 (10)	−0.0056 (10)	0.0066 (10)	0.0048 (9)
O6W	0.0620 (17)	0.0366 (14)	0.0452 (12)	0.0151 (12)	0.0291 (12)	0.0126 (10)
O6	0.0850 (19)	0.0275 (13)	0.0391 (11)	0.0028 (12)	−0.0075 (12)	−0.0026 (10)
O7W	0.0489 (17)	0.0568 (18)	0.0733 (16)	0.0085 (13)	0.0140 (13)	0.0192 (14)
O7	0.0420 (14)	0.0323 (13)	0.0552 (13)	0.0002 (11)	0.0058 (11)	0.0082 (10)
O8	0.0469 (16)	0.0452 (15)	0.0470 (13)	−0.0055 (12)	0.0065 (11)	0.0075 (10)
O8W	0.115 (3)	0.0616 (19)	0.0827 (19)	0.0341 (19)	0.0517 (19)	0.0138 (16)
O9W	0.0445 (16)	0.0475 (17)	0.0584 (16)	0.0085 (14)	−0.0037 (13)	−0.0078 (13)
C1	0.040 (2)	0.041 (2)	0.0430 (17)	0.0031 (16)	0.0013 (15)	−0.0073 (15)
C2	0.051 (2)	0.042 (2)	0.061 (2)	0.0047 (18)	0.0050 (18)	−0.0142 (17)
C3	0.047 (2)	0.032 (2)	0.080 (3)	0.0069 (17)	0.0096 (19)	0.0036 (18)
C4	0.034 (2)	0.037 (2)	0.0546 (19)	0.0015 (16)	0.0040 (15)	0.0088 (16)
C5	0.046 (2)	0.049 (2)	0.067 (2)	0.0035 (19)	0.0087 (18)	0.0227 (19)
C6	0.046 (2)	0.062 (3)	0.048 (2)	0.0006 (19)	0.0068 (17)	0.0248 (18)
C7	0.0276 (18)	0.057 (2)	0.0373 (16)	−0.0055 (16)	0.0056 (14)	0.0055 (15)
C8	0.0247 (17)	0.0343 (18)	0.0404 (16)	−0.0015 (14)	0.0018 (13)	0.0021 (14)
C9	0.0231 (17)	0.0380 (19)	0.0360 (15)	−0.0038 (14)	0.0036 (13)	0.0057 (13)
C10	0.043 (2)	0.072 (3)	0.0354 (17)	−0.008 (2)	0.0093 (16)	0.0033 (18)
C11	0.046 (2)	0.070 (3)	0.0389 (18)	−0.006 (2)	0.0102 (16)	−0.0157 (17)
C12	0.045 (2)	0.044 (2)	0.0459 (18)	0.0017 (17)	0.0081 (16)	−0.0065 (16)
C13	0.0323 (18)	0.0343 (18)	0.0321 (15)	0.0024 (14)	0.0101 (13)	0.0015 (13)
C14	0.0398 (19)	0.0258 (17)	0.0329 (15)	0.0004 (14)	0.0081 (14)	0.0028 (12)
C15	0.0407 (19)	0.0265 (17)	0.0334 (15)	−0.0006 (14)	0.0059 (14)	0.0087 (13)
C16	0.040 (2)	0.0321 (18)	0.0327 (15)	0.0024 (15)	0.0025 (14)	0.0057 (13)
C17	0.042 (2)	0.0303 (18)	0.0378 (16)	0.0029 (15)	−0.0010 (14)	−0.0046 (13)
C18	0.044 (2)	0.0290 (17)	0.0388 (16)	0.0024 (15)	0.0048 (14)	0.0067 (13)
C19	0.041 (2)	0.0363 (19)	0.0353 (15)	0.0046 (16)	0.0155 (14)	0.0081 (14)
C20	0.0342 (18)	0.0302 (17)	0.0258 (14)	−0.0016 (14)	0.0025 (13)	0.0018 (12)
C21	0.0338 (18)	0.0262 (17)	0.0314 (15)	−0.0027 (14)	0.0086 (13)	0.0016 (13)
C22	0.061 (3)	0.0277 (19)	0.0520 (19)	−0.0018 (17)	−0.0109 (17)	−0.0066 (15)
C23	0.047 (2)	0.035 (2)	0.0256 (14)	0.0019 (17)	0.0007 (14)	−0.0030 (13)

Co1—O5Wi	2.0144 (19)	O8W—H8WB	0.845 (18)
Co1—O5W	2.0144 (19)	O8W—H8WA	0.842 (18)
Co1—O6Wi	2.112 (2)	O9W—H9WA	0.833 (17)
Co1—O6W	2.112 (2)	O9W—H9WB	0.819 (18)
Co1—O7W	2.115 (3)	C1—C2	1.392 (5)
Co1—O7Wi	2.115 (3)	C1—H1A	0.9300
Co2—O2W	2.072 (2)	C2—C3	1.358 (5)
Co2—O1W	2.093 (2)	C2—H2A	0.9300
Co2—O4W	2.102 (2)	C3—C4	1.390 (4)
Co2—N1	2.109 (2)	C3—H3A	0.9300
Co2—O3W	2.118 (2)	C4—C8	1.393 (4)
Co2—N2	2.157 (2)	C4—C5	1.437 (4)
N1—C1	1.321 (4)	C5—C6	1.344 (5)
N1—C8	1.362 (3)	C5—H5A	0.9300
N2—C12	1.327 (4)	C6—C7	1.426 (5)
N2—C9	1.348 (4)	C6—H6A	0.9300
O1W—H1WA	0.816 (17)	C7—C10	1.399 (5)
O1W—H1WB	0.839 (17)	C7—C9	1.415 (4)
O1—C19	1.244 (3)	C8—C9	1.436 (4)
O2W—H2WA	0.856 (17)	C10—C11	1.350 (5)
O2W—H2WB	0.846 (17)	C10—H10A	0.9300
O2—C19	1.266 (3)	C11—C12	1.406 (4)
O3W—H3WA	0.831 (17)	C11—H11A	0.9300
O3W—H3WB	0.788 (17)	C12—H12A	0.9300
O3—C15	1.372 (3)	C13—C14	1.361 (4)
O3—C20	1.412 (3)	C13—C18	1.384 (4)
O4—C21	1.241 (3)	C13—C19	1.501 (3)
O4W—H4WA	0.841 (17)	C14—C15	1.395 (3)
O4W—H4WB	0.837 (17)	C14—H14A	0.9300
O5W—H5WA	0.837 (17)	C15—C16	1.370 (4)
O5W—H5WB	0.826 (18)	C16—C17	1.398 (4)
O5—C21	1.261 (3)	C16—H16A	0.9300
O6W—H6WA	0.788 (17)	C17—C18	1.375 (4)
O6W—H6WB	0.810 (17)	C18—H18A	0.9300
O6—C17	1.375 (3)	C20—C21	1.511 (4)
O6—C22	1.424 (4)	C20—H20A	0.9700
O7W—H7WA	0.836 (18)	C20—H20B	0.9700
O7W—H7WB	0.834 (18)	C22—C23	1.515 (4)
O7—C23	1.266 (4)	C22—H22A	0.9700
O8—C23	1.239 (4)	C22—H22B	0.9700
O5Wi—Co1—O5W	180.00 (8)	C2—C3—H3A	119.9
O5Wi—Co1—O6Wi	88.01 (8)	C4—C3—H3A	119.9
O5W—Co1—O6Wi	91.99 (8)	C3—C4—C8	117.3 (3)
O5Wi—Co1—O6W	91.99 (8)	C3—C4—C5	123.8 (3)
O5W—Co1—O6W	88.01 (8)	C8—C4—C5	118.9 (3)
O6Wi—Co1—O6W	180.000 (1)	C6—C5—C4	120.9 (3)
O5Wi—Co1—O7W	90.96 (12)	C6—C5—H5A	119.5
O5W—Co1—O7W	89.04 (12)	C4—C5—H5A	119.5
O6Wi—Co1—O7W	91.08 (10)	C5—C6—C7	121.6 (3)
O6W—Co1—O7W	88.92 (10)	C5—C6—H6A	119.2
O5Wi—Co1—O7Wi	89.04 (12)	C7—C6—H6A	119.2
O5W—Co1—O7Wi	90.96 (12)	C10—C7—C9	116.4 (3)
O6Wi—Co1—O7Wi	88.92 (10)	C10—C7—C6	124.6 (3)
O6W—Co1—O7Wi	91.08 (10)	C9—C7—C6	118.9 (3)
O7W—Co1—O7Wi	180.0	N1—C8—C4	123.0 (3)
O2W—Co2—O1W	91.48 (10)	N1—C8—C9	116.5 (3)
O2W—Co2—O4W	85.09 (9)	C4—C8—C9	120.5 (3)
O1W—Co2—O4W	86.82 (10)	N2—C9—C7	123.5 (3)
O2W—Co2—N1	165.12 (9)	N2—C9—C8	117.5 (2)
O1W—Co2—N1	99.13 (10)	C7—C9—C8	119.0 (3)
O4W—Co2—N1	85.11 (9)	C11—C10—C7	120.1 (3)
O2W—Co2—O3W	93.59 (10)	C11—C10—H10A	119.9
O1W—Co2—O3W	83.29 (9)	C7—C10—H10A	119.9
O4W—Co2—O3W	169.99 (9)	C10—C11—C12	119.8 (3)
N1—Co2—O3W	97.97 (10)	C10—C11—H11A	120.1
O2W—Co2—N2	95.03 (9)	C12—C11—H11A	120.1
O1W—Co2—N2	164.28 (10)	N2—C12—C11	122.2 (3)
O4W—Co2—N2	107.96 (10)	N2—C12—H12A	118.9
N1—Co2—N2	77.42 (9)	C11—C12—H12A	118.9
O3W—Co2—N2	82.04 (8)	C14—C13—C18	121.1 (2)
C1—N1—C8	117.2 (3)	C14—C13—C19	120.8 (3)
C1—N1—Co2	127.8 (2)	C18—C13—C19	118.1 (3)
C8—N1—Co2	114.98 (19)	C13—C14—C15	119.6 (3)
C12—N2—C9	118.0 (3)	C13—C14—H14A	120.2
C12—N2—Co2	128.2 (2)	C15—C14—H14A	120.2
C9—N2—Co2	113.33 (17)	C16—C15—O3	124.6 (2)
Co2—O1W—H1WA	131 (2)	C16—C15—C14	120.6 (3)
Co2—O1W—H1WB	117 (2)	O3—C15—C14	114.8 (3)
H1WA—O1W—H1WB	108 (2)	C15—C16—C17	118.7 (3)
Co2—O2W—H2WA	111 (2)	C15—C16—H16A	120.6
Co2—O2W—H2WB	118 (2)	C17—C16—H16A	120.6
H2WA—O2W—H2WB	99 (2)	C18—C17—O6	124.8 (3)
Co2—O3W—H3WA	122 (2)	C18—C17—C16	121.1 (3)
Co2—O3W—H3WB	127 (2)	O6—C17—C16	114.1 (2)
H3WA—O3W—H3WB	109 (3)	C17—C18—C13	118.9 (3)
C15—O3—C20	119.3 (2)	C17—C18—H18A	120.6
Co2—O4W—H4WA	126 (2)	C13—C18—H18A	120.6
Co2—O4W—H4WB	129 (2)	O1—C19—O2	123.0 (2)
H4WA—O4W—H4WB	103 (2)	O1—C19—C13	117.9 (3)
Co1—O5W—H5WA	121 (2)	O2—C19—C13	119.0 (3)
Co1—O5W—H5WB	128 (2)	O3—C20—C21	109.0 (2)
H5WA—O5W—H5WB	107 (2)	O3—C20—H20A	109.9
Co1—O6W—H6WA	128 (2)	C21—C20—H20A	109.9
Co1—O6W—H6WB	119 (2)	O3—C20—H20B	109.9
H6WA—O6W—H6WB	112 (3)	C21—C20—H20B	109.9
C17—O6—C22	116.8 (2)	H20A—C20—H20B	108.3
Co1—O7W—H7WA	119 (2)	O4—C21—O5	125.2 (3)
Co1—O7W—H7WB	115 (3)	O4—C21—C20	119.3 (2)
H7WA—O7W—H7WB	103 (2)	O5—C21—C20	115.5 (2)
H8WB—O8W—H8WA	103 (2)	O6—C22—C23	114.4 (3)
H9WA—O9W—H9WB	107 (3)	O6—C22—H22A	108.6
N1—C1—C2	123.5 (3)	C23—C22—H22A	108.6
N1—C1—H1A	118.3	O6—C22—H22B	108.6
C2—C1—H1A	118.3	C23—C22—H22B	108.6
C3—C2—C1	118.7 (3)	H22A—C22—H22B	107.6
C3—C2—H2A	120.7	O8—C23—O7	125.8 (3)
C1—C2—H2A	120.7	O8—C23—C22	119.9 (3)
C2—C3—C4	120.2 (3)	O7—C23—C22	114.3 (3)
O2W—Co2—N1—C1	−114.6 (4)	Co2—N2—C9—C8	5.0 (3)
O1W—Co2—N1—C1	20.4 (3)	C10—C7—C9—N2	1.2 (4)
O4W—Co2—N1—C1	−65.6 (3)	C6—C7—C9—N2	−179.7 (3)
O3W—Co2—N1—C1	104.8 (3)	C10—C7—C9—C8	−177.0 (3)
N2—Co2—N1—C1	−175.2 (3)	C6—C7—C9—C8	2.1 (4)
O2W—Co2—N1—C8	63.3 (4)	N1—C8—C9—N2	−2.8 (4)
O1W—Co2—N1—C8	−161.7 (2)	C4—C8—C9—N2	177.6 (3)
O4W—Co2—N1—C8	112.3 (2)	N1—C8—C9—C7	175.5 (3)
O3W—Co2—N1—C8	−77.3 (2)	C4—C8—C9—C7	−4.1 (4)
N2—Co2—N1—C8	2.66 (19)	C9—C7—C10—C11	−0.8 (5)
O2W—Co2—N2—C12	17.1 (3)	C6—C7—C10—C11	−179.8 (3)
O1W—Co2—N2—C12	−97.0 (4)	C7—C10—C11—C12	−0.2 (5)
O4W—Co2—N2—C12	103.6 (3)	C9—N2—C12—C11	−0.5 (5)
N1—Co2—N2—C12	−175.9 (3)	Co2—N2—C12—C11	170.9 (2)
O3W—Co2—N2—C12	−75.8 (3)	C10—C11—C12—N2	0.9 (5)
O2W—Co2—N2—C9	−171.1 (2)	C18—C13—C14—C15	0.2 (4)
O1W—Co2—N2—C9	74.8 (4)	C19—C13—C14—C15	179.3 (3)
O4W—Co2—N2—C9	−84.6 (2)	C20—O3—C15—C16	2.9 (4)
N1—Co2—N2—C9	−4.08 (19)	C20—O3—C15—C14	−177.2 (3)
O3W—Co2—N2—C9	96.0 (2)	C13—C14—C15—C16	0.7 (5)
C8—N1—C1—C2	0.5 (5)	C13—C14—C15—O3	−179.2 (3)
Co2—N1—C1—C2	178.4 (2)	O3—C15—C16—C17	179.5 (3)
N1—C1—C2—C3	2.1 (5)	C14—C15—C16—C17	−0.5 (5)
C1—C2—C3—C4	−2.0 (5)	C22—O6—C17—C18	5.8 (5)
C2—C3—C4—C8	−0.5 (5)	C22—O6—C17—C16	−173.9 (3)
C2—C3—C4—C5	178.8 (3)	C15—C16—C17—C18	−0.7 (5)
C3—C4—C5—C6	179.8 (3)	C15—C16—C17—O6	179.0 (3)
C8—C4—C5—C6	−0.9 (5)	O6—C17—C18—C13	−178.0 (3)
C4—C5—C6—C7	−1.1 (5)	C16—C17—C18—C13	1.6 (5)
C5—C6—C7—C10	179.4 (3)	C14—C13—C18—C17	−1.4 (5)
C5—C6—C7—C9	0.5 (5)	C19—C13—C18—C17	179.5 (3)
C1—N1—C8—C4	−3.2 (4)	C14—C13—C19—O1	−162.3 (3)
Co2—N1—C8—C4	178.6 (2)	C18—C13—C19—O1	16.8 (4)
C1—N1—C8—C9	177.2 (3)	C14—C13—C19—O2	17.1 (4)
Co2—N1—C8—C9	−1.0 (3)	C18—C13—C19—O2	−163.8 (3)
C3—C4—C8—N1	3.3 (5)	C15—O3—C20—C21	−178.3 (2)
C5—C4—C8—N1	−176.1 (3)	O3—C20—C21—O4	−0.9 (4)
C3—C4—C8—C9	−177.2 (3)	O3—C20—C21—O5	179.7 (2)
C5—C4—C8—C9	3.5 (4)	C17—O6—C22—C23	−81.3 (3)
C12—N2—C9—C7	−0.6 (4)	O6—C22—C23—O8	−4.5 (4)
Co2—N2—C9—C7	−173.3 (2)	O6—C22—C23—O7	177.7 (2)
C12—N2—C9—C8	177.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4W—H4WA···O7ii	0.84 (2)	1.88 (2)	2.713 (3)	173 (3)
O2W—H2WA···O8ii	0.86 (2)	1.86 (2)	2.690 (3)	163 (3)
O8W—H8WA···O1ii	0.84 (2)	1.91 (2)	2.732 (3)	163 (4)
O4W—H4WB···O2iii	0.84 (2)	1.91 (2)	2.731 (3)	169 (3)
O7W—H7WA···O9Wiii	0.84 (2)	2.01 (2)	2.818 (3)	164 (3)
O8W—H8WB···O4iii	0.85 (2)	2.29 (3)	2.945 (3)	134 (4)
O3W—H3WA···O7i	0.83 (2)	2.12 (2)	2.881 (3)	152 (3)
O5W—H5WA···O1i	0.84 (2)	1.77 (2)	2.609 (3)	175 (4)
O1W—H1WB···O7i	0.84 (2)	1.88 (2)	2.711 (3)	170 (3)
O6W—H6WB···O5iv	0.81 (2)	2.00 (2)	2.812 (3)	177 (3)
O5W—H5WB···O4iv	0.83 (2)	1.89 (2)	2.715 (3)	174 (4)
O3W—H3WB···O4iv	0.79 (2)	2.25 (2)	3.029 (3)	168 (4)
O3W—H3WB···O3iv	0.79 (2)	2.54 (3)	3.080 (3)	127 (3)
O9W—H9WB···O2v	0.82 (2)	2.00 (2)	2.818 (3)	172 (4)
O7W—H7WB···O9Wvi	0.83 (2)	1.97 (2)	2.805 (4)	174 (4)
O1W—H1WA···O5vii	0.82 (2)	1.97 (2)	2.785 (3)	172 (4)
O6W—H6WA···O2	0.79 (2)	2.00 (2)	2.775 (3)	169 (3)
O2W—H2WB···O8W	0.85 (2)	1.88 (2)	2.723 (3)	177 (3)
O9W—H9WA···O5	0.83 (2)	2.00 (2)	2.831 (3)	173 (3)

Table 1

Selected bond lengths (Å)

Co1—O5W	2.0144 (19)
Co1—O6W	2.112 (2)
Co1—O7W	2.115 (3)
Co2—O2W	2.072 (2)
Co2—O1W	2.093 (2)
Co2—O4W	2.102 (2)
Co2—N1	2.109 (2)
Co2—O3W	2.118 (2)
Co2—N2	2.157 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4W—H4WA⋯O7i	0.84 (2)	1.88 (2)	2.713 (3)	173 (3)
O2W—H2WA⋯O8i	0.86 (2)	1.86 (2)	2.690 (3)	163 (3)
O8W—H8WA⋯O1i	0.84 (2)	1.91 (2)	2.732 (3)	163 (4)
O4W—H4WB⋯O2ii	0.84 (2)	1.91 (2)	2.731 (3)	169 (3)
O7W—H7WA⋯O9Wii	0.84 (2)	2.01 (2)	2.818 (3)	164 (3)
O8W—H8WB⋯O4ii	0.85 (2)	2.29 (3)	2.945 (3)	134 (4)
O3W—H3WA⋯O7iii	0.83 (2)	2.12 (2)	2.881 (3)	152 (3)
O5W—H5WA⋯O1iii	0.84 (2)	1.77 (2)	2.609 (3)	175 (4)
O1W—H1WB⋯O7iii	0.84 (2)	1.88 (2)	2.711 (3)	170 (3)
O6W—H6WB⋯O5iv	0.81 (2)	2.00 (2)	2.812 (3)	177 (3)
O5W—H5WB⋯O4iv	0.83 (2)	1.89 (2)	2.715 (3)	174 (4)
O3W—H3WB⋯O4iv	0.79 (2)	2.25 (2)	3.029 (3)	168 (4)
O3W—H3WB⋯O3iv	0.79 (2)	2.54 (3)	3.080 (3)	127 (3)
O9W—H9WB⋯O2v	0.82 (2)	2.00 (2)	2.818 (3)	172 (4)
O7W—H7WB⋯O9Wvi	0.83 (2)	1.97 (2)	2.805 (4)	174 (4)
O1W—H1WA⋯O5vii	0.82 (2)	1.97 (2)	2.785 (3)	172 (4)
O6W—H6WA⋯O2	0.79 (2)	2.00 (2)	2.775 (3)	169 (3)
O2W—H2WB⋯O8W	0.85 (2)	1.88 (2)	2.723 (3)	177 (3)
O9W—H9WA⋯O5	0.83 (2)	2.00 (2)	2.831 (3)	173 (3)

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