Hexakis(1H-imidazole-κN)cobalt(II) triaqua-tris(1H-imidazole-κN)cobalt(II) bis-(naphthalene-1,4-dicarboxyl-ate).

The asymmetric unit of the title compound, [Co(C(3)H(4)N(2))(6)][Co(C(3)H(4)N(2))(3)(H(2)O)(3)](C(12)H(6)O(4))(2), contains two halves of crystallographically independent Co(II) complex cations, each assuming a distorted octa-hedral geometry, and one uncoordinated naphthalene-1,4-dicarboxyl-ate dianion. One Co(II) cation is located on an inversion center and is coordinated by six imidazole mol-ecules, while the other Co(II) cation is located on a twofold rotation axis and is coordinated by three water and three imidazole mol-ecules. The uncoordinated naphthalene-1,4-dicarboxyl-ate dianion links both Co(II) complex cations via O-H⋯O and N-H⋯O hydrogen bonding. One imidazole ligand is equally disordered over two sites about a twofold rotation axis, while the coordinated N atom of the imidazole is located on the twofold rotation axis. One water O atom has site symmetry 2.

Related literature

For general background to the nature of π-π stacking, see: Su & Xu (2004 ▶); Xu et al. (2007 ▶). For related structures, see: Derissen et al. (1979 ▶); Li et al. (2008a ▶,b ▶).

Experimental

Crystal data

[Co(C3H4N2)6][Co(C3H4N2)3(H2O)3](C12H6O4)2

M = 1212.98

Orthorhombic,

a = 29.388 (3) Å

b = 9.3275 (11) Å

c = 20.475 (2) Å

V = 5612.5 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.67 mm−1

T = 294 K

0.36 × 0.32 × 0.26 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.735, T max = 0.840

57832 measured reflections

5058 independent reflections

3916 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.07

5058 reflections

367 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.41 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023794/hk2715sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023794/hk2715Isup2.hkl

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

[Co(C3H4N2)6][Co(C3H4N2)3(H2O)3](C12H6O4)2	F(000) = 2512
Mr = 1212.98	Dx = 1.436 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 5022 reflections
a = 29.388 (3) Å	θ = 1.6–25.0°
b = 9.3275 (11) Å	µ = 0.67 mm−1
c = 20.475 (2) Å	T = 294 K
V = 5612.5 (10) Å3	Prism, pink
Z = 4	0.36 × 0.32 × 0.26 mm

Rigaku R-AXIS RAPID IP diffractometer	5058 independent reflections
Radiation source: fine-focus sealed tube	3916 reflections with I > 2σ(I)
graphite	Rint = 0.061
Detector resolution: 10.0 pixels mm-1	θmax = 25.2°, θmin = 1.4°
ω scans	h = −35→33
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.735, Tmax = 0.840	l = −23→24
57832 measured reflections

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-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0416P)2 + 3.4164P] where P = (Fo2 + 2Fc2)/3
5058 reflections	(Δ/σ)max = 0.001
367 parameters	Δρmax = 0.82 e Å−3
5 restraints	Δρmin = −0.41 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	0.5000	0.0000	0.5000	0.03475 (13)
Co2	0.7500	0.7500	0.54463 (2)	0.03692 (14)
N1	0.53139 (7)	0.2076 (2)	0.50438 (10)	0.0415 (5)
N2	0.58320 (9)	0.3736 (3)	0.49130 (13)	0.0592 (7)
H2N	0.6056	0.4202	0.4747	0.071*
N3	0.54621 (7)	−0.0709 (2)	0.57572 (10)	0.0408 (5)
N4	0.58380 (8)	−0.2194 (2)	0.63945 (11)	0.0500 (6)
H4N	0.5921	−0.2979	0.6580	0.060*
N5	0.45060 (7)	0.0639 (2)	0.57347 (10)	0.0434 (5)
N6	0.41451 (9)	0.0695 (3)	0.66759 (12)	0.0575 (6)
H6N	0.4088	0.0574	0.7084	0.069*
N7	0.72100 (8)	0.9634 (2)	0.54290 (11)	0.0467 (5)
N8	0.69494 (9)	1.1752 (3)	0.57111 (14)	0.0601 (7)
H8N	0.6866	1.2456	0.5955	0.072*
O1	0.65890 (7)	0.0726 (2)	0.13247 (9)	0.0575 (5)
O2	0.60816 (7)	−0.02645 (19)	0.19969 (9)	0.0536 (5)
O3	0.69702 (9)	0.6180 (3)	0.35989 (10)	0.0910 (9)
O4	0.65260 (7)	0.5131 (2)	0.43005 (9)	0.0614 (6)
O1W	0.68251 (6)	0.65158 (18)	0.54162 (8)	0.0453 (4)
H1A	0.6733	0.6170	0.5012	0.068*
H1B	0.6772	0.5888	0.5708	0.068*
O2W	0.7500	0.7500	0.44381 (11)	0.0510 (7)
H2A	0.7342	0.6989	0.4182	0.077*
C1	0.56663 (11)	0.2500 (3)	0.47050 (15)	0.0567 (8)
H1	0.5787	0.1988	0.4356	0.068*
C2	0.55829 (13)	0.4123 (3)	0.54329 (19)	0.0742 (10)
H2	0.5624	0.4933	0.5691	0.089*
C3	0.52607 (12)	0.3104 (3)	0.55061 (16)	0.0646 (9)
H3	0.5036	0.3106	0.5826	0.078*
C4	0.55044 (10)	−0.2038 (3)	0.59620 (13)	0.0495 (7)
H4	0.5321	−0.2788	0.5820	0.059*
C5	0.60213 (11)	−0.0882 (3)	0.64854 (17)	0.0675 (9)
H5	0.6260	−0.0648	0.6765	0.081*
C6	0.57913 (11)	0.0025 (3)	0.60917 (16)	0.0602 (8)
H6	0.5848	0.1003	0.6053	0.072*
C7	0.45256 (10)	0.0328 (3)	0.63626 (13)	0.0499 (7)
H7	0.4775	−0.0098	0.6563	0.060*
C8	0.38665 (12)	0.1295 (4)	0.62264 (17)	0.0712 (9)
H8	0.3577	0.1665	0.6300	0.085*
C9	0.40880 (11)	0.1255 (4)	0.56533 (16)	0.0639 (9)
H9	0.3974	0.1595	0.5259	0.077*
C10	0.71170 (11)	1.0496 (3)	0.59131 (16)	0.0599 (8)
H10	0.7162	1.0263	0.6350	0.072*
C11	0.69356 (13)	1.1707 (4)	0.50581 (19)	0.0776 (11)
H11	0.6836	1.2429	0.4779	0.093*
C12	0.70948 (13)	1.0405 (4)	0.48858 (17)	0.0750 (10)
H12	0.7122	1.0078	0.4459	0.090*
C20	0.65783 (9)	0.4146 (3)	0.32301 (12)	0.0404 (6)
C21	0.69252 (10)	0.3443 (3)	0.29285 (14)	0.0558 (8)
H21	0.7224	0.3683	0.3032	0.067*
C22	0.68432 (10)	0.2362 (3)	0.24652 (14)	0.0535 (7)
H22	0.7088	0.1905	0.2267	0.064*
C23	0.64097 (9)	0.1970 (3)	0.23010 (12)	0.0391 (6)
C24	0.60349 (8)	0.2713 (2)	0.25851 (11)	0.0358 (6)
C25	0.55755 (9)	0.2425 (3)	0.24077 (13)	0.0446 (6)
H25	0.5514	0.1701	0.2108	0.054*
C26	0.52253 (10)	0.3182 (3)	0.26665 (14)	0.0539 (7)
H26	0.4928	0.2956	0.2551	0.065*
C27	0.53077 (10)	0.4302 (3)	0.31069 (14)	0.0559 (8)
H27	0.5066	0.4831	0.3272	0.067*
C28	0.57421 (10)	0.4620 (3)	0.32946 (13)	0.0463 (7)
H28	0.5792	0.5366	0.3587	0.056*
C29	0.61191 (8)	0.3829 (2)	0.30492 (11)	0.0368 (6)
C30	0.66975 (10)	0.5234 (3)	0.37521 (13)	0.0467 (7)
C31	0.63550 (9)	0.0723 (3)	0.18330 (13)	0.0425 (6)
N9	0.7500	0.7500	0.64726 (14)	0.0532 (6)
N10	0.76923 (15)	0.7145 (5)	0.74775 (19)	0.0532 (6)	0.50
H10A	0.7858	0.7124	0.7823	0.064*	0.50
C13	0.78454 (12)	0.7510 (6)	0.68841 (17)	0.0532 (6)	0.50
H13	0.8145	0.7733	0.6780	0.064*	0.50
C14	0.72418 (16)	0.6813 (6)	0.7466 (2)	0.0532 (6)	0.50
H14	0.7056	0.6512	0.7806	0.064*	0.50
C15	0.71334 (12)	0.7034 (6)	0.68278 (19)	0.0532 (6)	0.50
H15	0.6845	0.6885	0.6653	0.064*	0.50

	U11	U22	U33	U12	U13	U23
Co1	0.0411 (3)	0.0299 (2)	0.0333 (2)	0.0009 (2)	0.0015 (2)	0.00306 (19)
Co2	0.0484 (3)	0.0339 (2)	0.0285 (2)	−0.0068 (2)	0.000	0.000
N1	0.0466 (13)	0.0354 (11)	0.0424 (12)	−0.0041 (10)	−0.0008 (10)	0.0050 (9)
N2	0.0621 (16)	0.0473 (14)	0.0682 (17)	−0.0199 (12)	−0.0011 (13)	0.0039 (12)
N3	0.0471 (13)	0.0333 (11)	0.0422 (12)	0.0041 (10)	−0.0022 (10)	0.0034 (9)
N4	0.0532 (14)	0.0460 (13)	0.0508 (14)	0.0101 (11)	−0.0043 (11)	0.0111 (11)
N5	0.0484 (14)	0.0390 (11)	0.0427 (13)	0.0013 (10)	0.0074 (10)	0.0017 (10)
N6	0.0685 (17)	0.0586 (15)	0.0454 (14)	−0.0035 (13)	0.0166 (13)	−0.0064 (12)
N7	0.0523 (14)	0.0396 (12)	0.0482 (13)	−0.0011 (10)	−0.0006 (11)	0.0016 (10)
N8	0.0638 (17)	0.0409 (13)	0.0755 (18)	0.0044 (12)	0.0103 (14)	−0.0018 (13)
O1	0.0802 (15)	0.0484 (11)	0.0438 (11)	−0.0076 (10)	0.0182 (10)	−0.0122 (9)
O2	0.0706 (14)	0.0447 (11)	0.0454 (11)	−0.0173 (10)	0.0079 (10)	−0.0124 (9)
O3	0.127 (2)	0.1031 (18)	0.0424 (12)	−0.0803 (17)	0.0085 (13)	−0.0151 (12)
O4	0.0803 (15)	0.0672 (13)	0.0368 (11)	−0.0317 (11)	0.0084 (10)	−0.0135 (9)
O1W	0.0565 (11)	0.0440 (10)	0.0355 (9)	−0.0124 (8)	0.0019 (8)	0.0015 (8)
O2W	0.0704 (18)	0.0545 (15)	0.0282 (13)	−0.0297 (14)	0.000	0.000
C1	0.067 (2)	0.0487 (16)	0.0548 (18)	−0.0153 (15)	0.0080 (15)	−0.0052 (14)
C2	0.086 (3)	0.0440 (18)	0.093 (3)	−0.0116 (17)	0.006 (2)	−0.0203 (17)
C3	0.071 (2)	0.0473 (16)	0.075 (2)	−0.0077 (16)	0.0161 (17)	−0.0168 (16)
C4	0.0554 (18)	0.0394 (14)	0.0536 (17)	−0.0004 (12)	−0.0081 (14)	0.0074 (12)
C5	0.069 (2)	0.0526 (18)	0.081 (2)	0.0016 (16)	−0.0325 (18)	0.0018 (17)
C6	0.064 (2)	0.0392 (15)	0.078 (2)	0.0010 (14)	−0.0231 (17)	0.0040 (15)
C7	0.0530 (17)	0.0553 (16)	0.0414 (16)	−0.0005 (13)	0.0080 (13)	−0.0039 (13)
C8	0.061 (2)	0.078 (2)	0.074 (2)	0.0181 (18)	0.0243 (19)	0.0008 (19)
C9	0.061 (2)	0.072 (2)	0.0585 (19)	0.0217 (17)	0.0084 (15)	0.0112 (16)
C10	0.083 (2)	0.0414 (15)	0.0557 (19)	0.0021 (15)	0.0067 (16)	0.0006 (14)
C11	0.093 (3)	0.060 (2)	0.080 (3)	0.0272 (19)	−0.006 (2)	0.0116 (18)
C12	0.104 (3)	0.064 (2)	0.057 (2)	0.025 (2)	−0.0131 (19)	0.0038 (16)
C20	0.0455 (16)	0.0407 (14)	0.0350 (13)	−0.0095 (12)	0.0003 (11)	−0.0058 (11)
C21	0.0394 (16)	0.070 (2)	0.0583 (18)	−0.0134 (14)	−0.0011 (14)	−0.0199 (15)
C22	0.0403 (16)	0.0631 (18)	0.0572 (18)	−0.0031 (14)	0.0063 (13)	−0.0204 (15)
C23	0.0419 (15)	0.0399 (13)	0.0354 (13)	−0.0045 (11)	0.0004 (11)	−0.0069 (11)
C24	0.0392 (14)	0.0375 (13)	0.0306 (12)	−0.0033 (11)	−0.0030 (10)	0.0008 (10)
C25	0.0427 (16)	0.0503 (15)	0.0409 (14)	−0.0045 (13)	−0.0054 (12)	−0.0050 (12)
C26	0.0368 (16)	0.0713 (19)	0.0536 (17)	0.0014 (14)	−0.0097 (13)	0.0009 (16)
C27	0.0486 (18)	0.0635 (19)	0.0557 (18)	0.0180 (15)	−0.0016 (14)	−0.0019 (15)
C28	0.0566 (18)	0.0408 (14)	0.0416 (15)	0.0073 (13)	−0.0019 (13)	−0.0067 (12)
C29	0.0443 (15)	0.0342 (12)	0.0318 (13)	−0.0026 (11)	−0.0011 (11)	−0.0024 (10)
C30	0.0586 (18)	0.0444 (15)	0.0373 (15)	−0.0163 (13)	−0.0036 (13)	−0.0058 (12)
C31	0.0500 (16)	0.0382 (14)	0.0394 (15)	−0.0008 (12)	−0.0014 (12)	−0.0079 (11)
N9	0.0688 (13)	0.0549 (14)	0.0359 (9)	0.0052 (12)	0.000	0.000
N10	0.0688 (13)	0.0549 (14)	0.0359 (9)	0.0052 (12)	0.000	0.000
C13	0.0688 (13)	0.0549 (14)	0.0359 (9)	0.0052 (12)	0.000	0.000
C14	0.0688 (13)	0.0549 (14)	0.0359 (9)	0.0052 (12)	0.000	0.000
C15	0.0688 (13)	0.0549 (14)	0.0359 (9)	0.0052 (12)	0.000	0.000

Co1—N1	2.146 (2)	C4—H4	0.9300
Co1—N1i	2.146 (2)	C5—C6	1.350 (4)
Co1—N3	2.165 (2)	C5—H5	0.9300
Co1—N3i	2.165 (2)	C6—H6	0.9300
Co1—N5	2.174 (2)	C7—H7	0.9300
Co1—N5i	2.174 (2)	C8—C9	1.342 (4)
Co2—O1Wii	2.1864 (17)	C8—H8	0.9300
Co2—O1W	2.1864 (17)	C9—H9	0.9300
Co2—O2W	2.064 (2)	C10—H10	0.9300
Co2—N7ii	2.166 (2)	C11—C12	1.348 (5)
Co2—N7	2.166 (2)	C11—H11	0.9300
Co2—N9	2.101 (3)	C12—H12	0.9300
N1—C1	1.308 (3)	C20—C21	1.361 (4)
N1—C3	1.356 (4)	C20—C29	1.430 (3)
N2—C1	1.322 (4)	C20—C30	1.515 (3)
N2—C2	1.341 (4)	C21—C22	1.405 (4)
N2—H2N	0.8600	C21—H21	0.9300
N3—C4	1.314 (3)	C22—C23	1.368 (4)
N3—C6	1.369 (4)	C22—H22	0.9300
N4—C4	1.329 (3)	C23—C24	1.426 (3)
N4—C5	1.350 (4)	C23—C31	1.515 (3)
N4—H4N	0.8600	C24—C25	1.424 (4)
N5—C7	1.319 (3)	C24—C29	1.431 (3)
N5—C9	1.366 (4)	C25—C26	1.356 (4)
N6—C7	1.334 (4)	C25—H25	0.9300
N6—C8	1.353 (4)	C26—C27	1.401 (4)
N6—H6N	0.8600	C26—H26	0.9300
N7—C10	1.305 (4)	C27—C28	1.366 (4)
N7—C12	1.367 (4)	C27—H27	0.9300
N8—C10	1.336 (4)	C28—C29	1.423 (4)
N8—C11	1.338 (4)	C28—H28	0.9300
N8—H8N	0.8600	N9—C13	1.3190 (10)
O1—C31	1.248 (3)	N9—C13ii	1.3190 (10)
O2—C31	1.268 (3)	N9—C15ii	1.3706 (10)
O3—C30	1.232 (3)	N9—C15	1.3706 (10)
O4—C30	1.234 (3)	N10—C13	1.3395 (10)
O1W—H1A	0.9287	N10—C14	1.3598 (10)
O1W—H1B	0.8504	N10—H10A	0.8600
O2W—H2A	0.8475	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.3597 (10)
C2—C3	1.350 (4)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—H3	0.9300
N1—Co1—N1i	180.00 (10)	N5—C7—N6	112.0 (3)
N1—Co1—N3	88.64 (8)	N5—C7—H7	124.0
N1i—Co1—N3	91.36 (8)	N6—C7—H7	124.0
N1—Co1—N3i	91.36 (8)	C9—C8—N6	106.8 (3)
N1i—Co1—N3i	88.64 (8)	C9—C8—H8	126.6
N3—Co1—N3i	180.00 (12)	N6—C8—H8	126.6
N1—Co1—N5	90.61 (8)	C8—C9—N5	110.0 (3)
N1i—Co1—N5	89.39 (8)	C8—C9—H9	125.0
N3—Co1—N5	90.41 (8)	N5—C9—H9	125.0
N3i—Co1—N5	89.59 (8)	N7—C10—N8	112.5 (3)
N1—Co1—N5i	89.38 (8)	N7—C10—H10	123.8
N1i—Co1—N5i	90.62 (8)	N8—C10—H10	123.8
N3—Co1—N5i	89.59 (8)	N8—C11—C12	106.2 (3)
N3i—Co1—N5i	90.41 (8)	N8—C11—H11	126.9
N5—Co1—N5i	180.00 (8)	C12—C11—H11	126.9
O2W—Co2—N9	180.000 (1)	C11—C12—N7	110.3 (3)
O2W—Co2—N7ii	89.06 (6)	C11—C12—H12	124.9
N9—Co2—N7ii	90.94 (6)	N7—C12—H12	124.8
O2W—Co2—N7	89.06 (6)	C21—C20—C29	119.3 (2)
N9—Co2—N7	90.94 (6)	C21—C20—C30	118.0 (2)
N7ii—Co2—N7	178.12 (12)	C29—C20—C30	122.7 (2)
O2W—Co2—O1Wii	88.38 (4)	C20—C21—C22	121.6 (3)
N9—Co2—O1Wii	91.62 (4)	C20—C21—H21	119.2
N7ii—Co2—O1Wii	91.63 (8)	C22—C21—H21	119.2
N7—Co2—O1Wii	88.32 (8)	C23—C22—C21	121.2 (3)
O2W—Co2—O1W	88.38 (4)	C23—C22—H22	119.4
N9—Co2—O1W	91.62 (4)	C21—C22—H22	119.4
N7ii—Co2—O1W	88.32 (8)	C22—C23—C24	119.3 (2)
N7—Co2—O1W	91.63 (8)	C22—C23—C31	117.4 (2)
O1Wii—Co2—O1W	176.77 (9)	C24—C23—C31	123.3 (2)
C1—N1—C3	104.3 (2)	C25—C24—C23	122.4 (2)
C1—N1—Co1	126.23 (19)	C25—C24—C29	118.1 (2)
C3—N1—Co1	128.12 (19)	C23—C24—C29	119.4 (2)
C1—N2—C2	106.8 (3)	C26—C25—C24	121.4 (2)
C1—N2—H2N	126.6	C26—C25—H25	119.3
C2—N2—H2N	126.6	C24—C25—H25	119.3
C4—N3—C6	104.2 (2)	C25—C26—C27	120.6 (3)
C4—N3—Co1	125.18 (18)	C25—C26—H26	119.7
C6—N3—Co1	130.43 (17)	C27—C26—H26	119.7
C4—N4—C5	106.7 (2)	C28—C27—C26	120.3 (3)
C4—N4—H4N	126.7	C28—C27—H27	119.8
C5—N4—H4N	126.7	C26—C27—H27	119.8
C7—N5—C9	104.5 (2)	C27—C28—C29	121.0 (2)
C7—N5—Co1	125.79 (19)	C27—C28—H28	119.5
C9—N5—Co1	129.15 (19)	C29—C28—H28	119.5
C7—N6—C8	106.6 (3)	C28—C29—C20	122.4 (2)
C7—N6—H6N	126.7	C28—C29—C24	118.5 (2)
C8—N6—H6N	126.7	C20—C29—C24	119.1 (2)
C10—N7—C12	104.0 (3)	O3—C30—O4	123.6 (2)
C10—N7—Co2	129.5 (2)	O3—C30—C20	116.8 (2)
C12—N7—Co2	126.5 (2)	O4—C30—C20	119.7 (2)
C10—N8—C11	107.0 (3)	O1—C31—O2	124.8 (2)
C10—N8—H8N	126.5	O1—C31—C23	117.9 (2)
C11—N8—H8N	126.5	O2—C31—C23	117.2 (2)
Co2—O1W—H1A	115.7	C13—N9—C13ii	100.6 (4)
Co2—O1W—H1B	115.8	C13ii—N9—C15ii	105.6 (3)
H1A—O1W—H1B	109.5	C13—N9—C15	105.6 (3)
Co2—O2W—H2A	128.3	C15ii—N9—C15	115.9 (5)
N1—C1—N2	112.6 (3)	C13—N9—Co2	129.7 (2)
N1—C1—H1	123.7	C13ii—N9—Co2	129.7 (2)
N2—C1—H1	123.7	C15ii—N9—Co2	122.0 (2)
N2—C2—C3	106.3 (3)	C15—N9—Co2	122.0 (2)
N2—C2—H2	126.8	C13—N10—C14	111.6 (4)
C3—C2—H2	126.8	C13—N10—H10A	124.2
C2—C3—N1	109.9 (3)	C14—N10—H10A	124.2
C2—C3—H3	125.1	N9—C13—N10	108.6 (4)
N1—C3—H3	125.1	N9—C13—H13	125.7
N3—C4—N4	112.7 (3)	N10—C13—H13	125.7
N3—C4—H4	123.7	C15—C14—N10	102.2 (4)
N4—C4—H4	123.7	C15—C14—C14ii	94.7 (3)
C6—C5—N4	106.6 (3)	C15—C14—H14	128.9
C6—C5—H5	126.7	N10—C14—H14	128.9
N4—C5—H5	126.7	C14ii—C14—H14	130.1
C5—C6—N3	109.8 (3)	C14—C15—N9	111.9 (4)
C5—C6—H6	125.1	C14—C15—H15	124.0
N3—C6—H6	125.1	N9—C15—H15	124.0

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O4	0.93	1.85	2.768 (3)	168
O1W—H1B···O1iii	0.85	2.04	2.883 (3)	173
O2W—H2A···O3	0.85	1.79	2.625 (3)	171
N2—H2N···O4	0.86	1.87	2.725 (3)	174
N4—H4N···O2iv	0.86	1.91	2.766 (3)	178
N6—H6N···O2i	0.86	1.97	2.827 (3)	176
N8—H8N···O1v	0.86	2.03	2.869 (3)	166
N10—H10A···O3vi	0.86	1.89	2.658 (5)	149

Table 1

Selected bond lengths (Å)

Co1—N1	2.146 (2)
Co1—N3	2.165 (2)
Co1—N5	2.174 (2)
Co2—O1W	2.1864 (17)
Co2—O2W	2.064 (2)
Co2—N7	2.166 (2)
Co2—N9	2.101 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O4	0.93	1.85	2.768 (3)	168
O1W—H1B⋯O1i	0.85	2.04	2.883 (3)	173
O2W—H2A⋯O3	0.85	1.79	2.625 (3)	171
N2—H2N⋯O4	0.86	1.87	2.725 (3)	174
N4—H4N⋯O2ii	0.86	1.91	2.766 (3)	178
N6—H6N⋯O2iii	0.86	1.97	2.827 (3)	176
N8—H8N⋯O1iv	0.86	2.03	2.869 (3)	166
N10—H10A⋯O3v	0.86	1.89	2.658 (5)	149

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