trans-Diaqua­bis(nicotinamide-κN)bis­(salicylato-κO)cobalt(II)

The title compound, [Co(C₇H₅O₃)₂(C₆H₆N₂O)₂(H₂O)₂], forms a three-dimensional hydrogen-bonded supra­molecular structure. The Co^II ion is in an octa­hedral coordination environment comprising two pyridyl N atoms, two carboxyl­ate O atoms and two O atoms from water mol­ecules. Inter­molecular N—H...O and O—H...O hydrogen bonds produce R₂²(8), R₂²(12) and R₂²(14) rings, which lead to two-dimensional chains. An extensive three-dimensional supra­molecular network of C—H...O, N—H...O and O—H...O hydrogen bonds and C—H...π inter­actions is responsible for crystal structure stabilization. This study is an example of the construction of a supra­molecular assembly based on hydrogen bonds in mixed-ligand metal complexes.

S1. Comment

Metal–organic supramolecular complexes with various fascinating topologies have been studied widely for their versatile chemical and physical properties and potential applications as functional materials (Janiak, 2003; Kitagawa et al., 2004; Yaghi et al., 2003). Self-assembly based on molecular building blocks has become an effective approach to construct these functional materials. In the development of supramolecular chemistry, hydrogen-bonding and π–π interactions, acting as the two main driving forces, play an important role in the self-assembly of multi-dimensional metal–organic supramolecular frameworks or networks (Graham & Pike, 2000; Mitzi et al., 1995). Some interesting coordination polymers assembled with 4,4'-bipyridine (bipy) have been reported, showing various structural motifs, including two-dimensional layers (Carlucci et al., 1997; Tong et al., 1998) and three-dimensional nets (Lu et al., 1998; Hagrman et al., 1998; Kondo et al., 1999; Greve et al., 2003; Zhang et al., 1999; Şahin et al., 2007). We report here the structure of the title complex, (I), in which hydrogen-bond interactions lead to a three-dimensional supramolecular network.

The molecular structure of (I) and the atom-labelling scheme are shown in Fig. 1. The Co^II ion is coordinated by two O atoms from two identical carboxylate groups, two O atoms from two water molecules and two pyridyl N atoms. The geometry around the Co^II ion (Table 1) is that of a slightly distorted octahedron. The distortion arises from the N1—Co1—N2 axis, which is not perfectly perpendicular to the coordination plane (O1/O2/O3/O4/Co1). The significant difference between the Co—O bond distances in the equatorial plane and the Co—N bond distances in the axial positions has also been observed in another cobalt complex (Şahin et al., 2007).

Molecules are linked by intermolecular hydrogen bonding, and we employ graph-set notation (Bernstein et al., 1995) to describe the patterns of hydrogen bonding. Molecules of (I) are linked into sheets by a combination of C—H···O, O—H···O and N—H···O hydrogen bonds (Table 2). Within the selected asymmetric unit, intramolecular O—H···O hydrogen bonds define S₂¹(10) and S(6) motifs (Fig. 1). Water atom O1 in the molecule at (x, y, z) acts as hydrogen-bond donor, via atoms H1A and H1B, respectively, to atom O5 at (x + 1, y, z) and atom O10 at (x + 1, y, z), so forming a C(6)C(8)[R₂²(12)] chain of rings running parallel to the [100] direction. Similarly, water atom O2 in the reference molecule at (x, y, z) acts as hydrogen-bond donor, via atom H2B, to atom O9 in the molecule at (x - 1, y, z), so forming a C(8) chain running parallel to the [100] direction. The combination of the C(6) and C(8) chains generates a chain of edge-fused R₂²(14) rings running parallel to the [100] direction (Fig. 2). Amino atom N4 in the reference molecule at (x, y, z) acts as hydrogen-bond donor, via atom H4A, to atom O10 in the molecule at (x + 1, y, z - 1), so forming a C(12) chain running parallel to the [101] direction (Fig. 3). Amino atom N3 in the molecule at (x, y, z) acts as hydrogen-bond donor, via atom H3A, to atom O9 in the molecule at (x - 1, y, z + 1), so forming a C(12) chain running parallel to the [101] direction. The combination of C(12) chains generates a chain of edge-fused R₂²(8) rings running parallel to the [101] direction (Fig. 3).

Fig. 4 shows the way in which amino atom N4, hydroxyl atom O6, atom C18 and carboxylate atom O5 enter into intermolecular hydrogen-bonding interactions. As a result, amino atom N4 in the reference molecule at (x, y, z) acts as hydrogen-bond donor, via atom H4B, to atom O6 in the molecule at (x, y, z - 1), so forming a C(12) chain running parallel to the [001] direction. At the same time, atom C18 in the reference molecule at (x, y, z) acts as hydrogen-bond donor, via atom H18, to atom O5 in the molecule at (-x, y - 1/2, -z), so forming a C(10) chain running parallel to the [010] direction. The combination of the C(10) and C(12) chains generates a chain of edge-fused R₄⁴(40) rings parallel to the bc plane (Fig. 4).

Compound (I) also contains two intermolecular C—H···π interactions. In the first, atom C9 in the molecule at (x, y, z) acts as hydrogen-bond donor to the C21–C26 benzene ring in the molecule at (x, y, z - 1), so forming a chain running parallel to the [001] direction. In the second, atom C3 in the molecule at (x, y, z) acts as hydrogen-bond donor to the C14–C19 benzene ring in the molecule at (x, y, z + 1), so forming a chain running parallel to the [001] direction. Details of these interactions are given in Table 2. The combination of C—H···π interactions defines an R₂²(20) ring pattern (Fig. 5).

The combination of the chains along [100], [101], [010] and [001] suffices to generate a three-dimensional structure of considerable complexity.

Related literature

For related literature, see: Bernstein et al. (1995); Carlucci et al. (1997); Graham & Pike (2000); Greve et al. (2003); Hagrman et al. (1998); Janiak (2003); Kitagawa et al. (2004); Kondo et al. (1999); Lu et al. (1998); Mitzi et al. (1995); Sheldrick (2008); Tong et al. (1998); Yaghi et al. (2003); Zhang et al. (1999); Şahin et al. (2007).

S2. Experimental

In the first step, salicylic acid sodium salt was prepared, and cobalt salicylate salt was synthesized from Na(SA) (SA = salicylic acid) salt. A solution of Co(SA)₂.nH₂O [In what solvent?] was left for 15 d at room temperature for crystallization. In the second step, a solution of nicotinamide (2 mmol) in distilled water (30 ml) was added dropwise to a stirred solution of Co(SA)₂.nH₂O (1 mmol) in hot distilled water (50 ml). The resulting solution was heated to 323 K in a temperature-controlled bath and stirred for 4 h, and then cooled to room temperature and left for 15–17 d for crystallization. The crystals which formed were filtered off, washed with cold water and acetone and dried in vacuo to give brown crystals in a yield of 84% (0.51 g). Analysis, found: C 50.38, H 4.12%; calculated for C₂₆H₂₈N₄O₁₀Co: C 50.86, H 4.57%.

S3. Refinement

H atoms bonded to C and N atoms were included in their expected positions and allowed to ride, with C—H and N—H distances restrained to 0.93 and 0.86 Å, respectively, and with U_iso(H) = 1.2U_eq(C,N). Water H atoms were located in a difference map and refined subject to a DFIX (SHELXL97; Sheldrick, 2008) restraint of O—H = 0.83 (2) Å. The H atoms of the hydroxy groups (O6 and O8) were allowed for with a fixed O—H distance of 0.82 Å [U_iso(H) = 1.5U_eq(O)].

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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).

Figures

	Fig. 1. A view of the molecule of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are indicated by dashed lines.
	Fig. 2. Part of the crystal structure of (I), showing the formation of R2^2(12) and R2^2(14) rings. Hydrogen bonds are indicated by dashed lines. H atoms not involved in these interactions have been omitted for clarity. (Symmetry codes as in Table 2).
	Fig. 3. Part of the crystal structure of (I), showing the formation of a R2^2(8) dimer. Hydrogen bonds are indicated by dashed lines. H atoms not involved in these interactions have been omitted for clarity. (Symmetry codes as in Table 2).
	Fig. 4. Part of the crystal structure of (I), showing the formation of a chain of edge-fused R4^4(40) rings. Hydrogen bonds are indicated by dashed lines. For the sake of clarity, H atoms not involved in the motif shown have been omitted. [Symmetry codes: (iii) x, y, z - 1; (vi) -x, y - 1/2, -z; (vii) x, y, z + 1; (viii) -x, y + 1/2, -z.]
	Fig. 5. Part of the crystal structure of (I), showing the formation of a chain along [001] generated by the C—H···π interactions (dashed lines). For the sake of clarity, H atoms not involved in the motif shown have been omitted. [Symmetry codes: (iii) x, y, z - 1; (vii) x, y, z + 1.]

trans-Diaquabis(nicotinamide-κN)bis(salicylato-κO)cobalt(II)

Crystal data

[Co(C7H5O3)2(C6H6N2O)2(H2O)2]	F(000) = 634
Mr = 613.44	Dx = 1.530 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2yb	Cell parameters from 9880 reflections
a = 7.0484 (4) Å	θ = 2.1–27.3°
b = 19.4249 (7) Å	µ = 0.71 mm^−1
c = 10.3331 (5) Å	T = 296 K
β = 109.774 (4)°	Prism, brown
V = 1331.33 (11) Å^3	0.48 × 0.39 × 0.36 mm
Z = 2

Data collection

Stoe IPDSII diffractometer	5360 independent reflections
Radiation source: fine-focus sealed tube	4725 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
Detector resolution: 6.67 pixels mm^-1	θmax = 26.5°, θmin = 2.1°
ω scans	h = −8→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −24→24
Tmin = 0.549, Tmax = 0.811	l = −12→11
9880 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.064P)^2 + 0.1543P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.003
5360 reflections	Δρmax = 0.38 e Å^−3
383 parameters	Δρmin = −0.67 e Å^−3
7 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.012 (16)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4559 (7)	0.1501 (2)	0.4983 (4)	0.0507 (9)
H1	0.5545	0.1413	0.4592	0.061*
C2	0.4618 (8)	0.1144 (2)	0.6136 (5)	0.0651 (12)
H2	0.5614	0.0817	0.6514	0.078*
C3	0.3163 (7)	0.1279 (2)	0.6735 (4)	0.0575 (10)
H3	0.3165	0.1040	0.7516	0.069*
C4	0.1726 (6)	0.17694 (19)	0.6160 (4)	0.0454 (8)
C5	0.1756 (6)	0.2094 (2)	0.4974 (4)	0.0464 (8)
H5	0.0756	0.2416	0.4562	0.056*
C6	0.0127 (7)	0.1981 (2)	0.6706 (4)	0.0504 (9)
C7	0.1489 (6)	0.3403 (2)	−0.0040 (4)	0.0485 (8)
H7	0.0509	0.3517	0.0341	0.058*
C8	0.1330 (7)	0.3674 (2)	−0.1314 (4)	0.0553 (10)
H8	0.0261	0.3961	−0.1779	0.066*
C9	0.2786 (7)	0.3509 (2)	−0.1876 (4)	0.0559 (10)
H9	0.2709	0.3682	−0.2731	0.067*
C10	0.4367 (6)	0.3083 (2)	−0.1158 (4)	0.0451 (8)
C11	0.4400 (6)	0.2837 (2)	0.0116 (4)	0.0462 (8)
H11	0.5461	0.2554	0.0612	0.055*
C12	0.6042 (6)	0.2856 (2)	−0.1645 (4)	0.0504 (9)
C13	0.3227 (6)	0.10799 (19)	0.1328 (4)	0.0482 (9)
C14	0.4161 (6)	0.06376 (19)	0.0500 (4)	0.0457 (8)
C15	0.5935 (7)	0.0848 (2)	0.0293 (4)	0.0513 (9)
H15	0.6570	0.1251	0.0706	0.062*
C16	0.6751 (8)	0.0470 (2)	−0.0509 (5)	0.0605 (10)
H16	0.7913	0.0620	−0.0658	0.073*
C17	0.5833 (8)	−0.0134 (2)	−0.1092 (5)	0.0653 (12)
H17	0.6402	−0.0395	−0.1621	0.078*
C18	0.4109 (9)	−0.0358 (2)	−0.0912 (5)	0.0682 (13)
H18	0.3490	−0.0760	−0.1337	0.082*
C19	0.3271 (7)	0.0020 (2)	−0.0086 (5)	0.0584 (10)
C20	0.0543 (6)	0.36403 (18)	0.3307 (4)	0.0434 (8)
C21	0.0796 (6)	0.42063 (19)	0.4346 (4)	0.0472 (8)
C22	−0.0864 (7)	0.4443 (2)	0.4651 (5)	0.0613 (11)
H22	−0.2129	0.4256	0.4194	0.074*
C23	−0.0667 (9)	0.4950 (3)	0.5620 (5)	0.0748 (14)
H23	−0.1787	0.5097	0.5826	0.090*
C24	0.1183 (11)	0.5234 (3)	0.6277 (6)	0.0817 (16)
H24	0.1306	0.5583	0.6916	0.098*
C25	0.2865 (9)	0.5013 (2)	0.6009 (5)	0.0704 (13)
H25	0.4119	0.5206	0.6474	0.085*
C26	0.2676 (7)	0.4494 (2)	0.5030 (4)	0.0518 (9)
N1	0.3147 (5)	0.19697 (16)	0.4394 (3)	0.0457 (7)
N2	0.2978 (5)	0.29893 (16)	0.0659 (3)	0.0446 (7)
N3	0.0194 (6)	0.1745 (2)	0.7931 (4)	0.0692 (11)
H3A	−0.0706	0.1871	0.8274	0.083*
H3B	0.1138	0.1467	0.8379	0.083*
N4	0.6131 (6)	0.3132 (2)	−0.2798 (4)	0.0673 (10)
H4A	0.7043	0.2999	−0.3125	0.081*
H4B	0.5278	0.3443	−0.3219	0.081*
O1	0.6036 (4)	0.28346 (16)	0.3536 (3)	0.0541 (7)
H1A	0.696 (6)	0.297 (3)	0.327 (5)	0.081*
H1B	0.654 (6)	0.255 (2)	0.413 (4)	0.081*
O2	0.0064 (5)	0.21115 (18)	0.1713 (3)	0.0585 (7)
H2A	0.023 (8)	0.1710 (14)	0.149 (6)	0.088*
H2B	−0.107 (5)	0.222 (2)	0.121 (5)	0.088*
O3	0.4119 (4)	0.16219 (13)	0.1839 (3)	0.0490 (6)
O4	0.2184 (4)	0.34197 (14)	0.3174 (3)	0.0490 (6)
O5	−0.1124 (4)	0.34022 (15)	0.2679 (3)	0.0541 (6)
O6	0.4403 (5)	0.42729 (19)	0.4848 (4)	0.0740 (9)
H6	0.4140	0.3956	0.4291	0.111*
O7	0.1586 (6)	0.08797 (17)	0.1435 (4)	0.0811 (11)
O8	0.1580 (6)	−0.02228 (19)	0.0089 (5)	0.0892 (12)
H8A	0.1231	0.0040	0.0589	0.134*
O9	0.7238 (5)	0.2410 (2)	−0.1014 (3)	0.0636 (8)
O10	−0.1223 (4)	0.2379 (2)	0.6058 (3)	0.0665 (9)
Co1	0.30510 (7)	0.24951 (2)	0.25339 (4)	0.04027 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.060 (2)	0.051 (2)	0.051 (2)	0.0054 (17)	0.0324 (19)	0.0034 (17)
C2	0.078 (3)	0.065 (3)	0.064 (3)	0.023 (2)	0.039 (2)	0.018 (2)
C3	0.067 (3)	0.065 (3)	0.050 (2)	0.009 (2)	0.031 (2)	0.0169 (19)
C4	0.054 (2)	0.050 (2)	0.0399 (17)	−0.0034 (16)	0.0256 (17)	0.0005 (15)
C5	0.056 (2)	0.050 (2)	0.0399 (17)	0.0080 (17)	0.0253 (17)	0.0086 (15)
C6	0.056 (2)	0.060 (2)	0.0411 (19)	−0.0030 (18)	0.0241 (18)	0.0041 (17)
C7	0.055 (2)	0.051 (2)	0.0478 (19)	0.0017 (17)	0.0276 (18)	0.0010 (16)
C8	0.063 (3)	0.057 (2)	0.049 (2)	0.011 (2)	0.023 (2)	0.0087 (18)
C9	0.069 (3)	0.062 (2)	0.0425 (19)	0.003 (2)	0.027 (2)	0.0114 (18)
C10	0.053 (2)	0.050 (2)	0.0391 (17)	−0.0033 (16)	0.0253 (16)	0.0000 (15)
C11	0.056 (2)	0.0516 (19)	0.0408 (18)	−0.0016 (17)	0.0299 (17)	0.0014 (15)
C12	0.063 (2)	0.058 (2)	0.0424 (19)	−0.003 (2)	0.0338 (19)	−0.0010 (17)
C13	0.058 (2)	0.046 (2)	0.052 (2)	0.0017 (17)	0.0331 (19)	0.0050 (16)
C14	0.055 (2)	0.0384 (18)	0.049 (2)	0.0025 (16)	0.0254 (18)	0.0001 (15)
C15	0.060 (2)	0.047 (2)	0.054 (2)	0.0014 (17)	0.0286 (19)	−0.0014 (16)
C16	0.071 (3)	0.061 (3)	0.057 (2)	0.007 (2)	0.032 (2)	0.002 (2)
C17	0.090 (4)	0.056 (3)	0.054 (2)	0.020 (2)	0.029 (2)	−0.0035 (19)
C18	0.087 (4)	0.045 (2)	0.066 (3)	0.003 (2)	0.017 (3)	−0.010 (2)
C19	0.063 (3)	0.045 (2)	0.068 (3)	0.0025 (19)	0.024 (2)	−0.0014 (19)
C20	0.052 (2)	0.0411 (18)	0.0450 (18)	0.0007 (15)	0.0264 (17)	0.0051 (14)
C21	0.060 (2)	0.0447 (19)	0.0442 (19)	0.0038 (17)	0.0273 (18)	0.0024 (15)
C22	0.067 (3)	0.066 (3)	0.058 (2)	0.011 (2)	0.030 (2)	−0.007 (2)
C23	0.088 (4)	0.081 (3)	0.064 (3)	0.020 (3)	0.037 (3)	−0.013 (2)
C24	0.129 (5)	0.058 (3)	0.061 (3)	0.016 (3)	0.037 (3)	−0.014 (2)
C25	0.098 (4)	0.055 (2)	0.057 (2)	−0.009 (2)	0.023 (3)	−0.011 (2)
C26	0.063 (2)	0.051 (2)	0.049 (2)	−0.0010 (18)	0.029 (2)	0.0022 (17)
N1	0.0539 (19)	0.0493 (17)	0.0427 (15)	0.0043 (14)	0.0280 (14)	0.0061 (13)
N2	0.0513 (18)	0.0483 (17)	0.0426 (15)	0.0005 (14)	0.0270 (14)	0.0016 (13)
N3	0.074 (3)	0.098 (3)	0.051 (2)	0.017 (2)	0.042 (2)	0.0243 (19)
N4	0.078 (3)	0.088 (3)	0.0505 (19)	0.016 (2)	0.0406 (19)	0.0195 (18)
O1	0.0514 (16)	0.0644 (17)	0.0521 (16)	−0.0047 (14)	0.0248 (13)	0.0077 (13)
O2	0.0491 (16)	0.0667 (18)	0.0598 (17)	0.0000 (14)	0.0186 (13)	−0.0014 (15)
O3	0.0603 (17)	0.0454 (14)	0.0523 (15)	−0.0019 (12)	0.0332 (13)	−0.0053 (11)
O4	0.0527 (15)	0.0508 (14)	0.0528 (15)	0.0008 (12)	0.0300 (12)	−0.0075 (12)
O5	0.0536 (16)	0.0557 (15)	0.0600 (16)	−0.0026 (13)	0.0283 (14)	−0.0040 (13)
O6	0.0613 (19)	0.086 (2)	0.077 (2)	−0.0092 (17)	0.0274 (18)	−0.0200 (18)
O7	0.082 (2)	0.0589 (18)	0.129 (3)	−0.0129 (17)	0.070 (2)	−0.015 (2)
O8	0.083 (3)	0.061 (2)	0.139 (4)	−0.0217 (18)	0.058 (3)	−0.022 (2)
O9	0.0727 (18)	0.079 (2)	0.0546 (14)	0.0161 (18)	0.0420 (14)	0.0117 (16)
O10	0.0638 (17)	0.099 (3)	0.0460 (13)	0.0195 (18)	0.0305 (13)	0.0125 (16)
Co1	0.0497 (2)	0.0426 (2)	0.03727 (19)	0.0004 (2)	0.02618 (17)	0.0007 (2)

Geometric parameters (Å, º)

C1—N1	1.334 (5)	C17—C18	1.361 (7)
C1—C2	1.367 (6)	C17—H17	0.9300
C1—H1	0.9300	C18—C19	1.399 (6)
C2—C3	1.390 (6)	C18—H18	0.9300
C2—H2	0.9300	C19—O8	1.350 (5)
C3—C4	1.370 (6)	C20—O5	1.225 (5)
C3—H3	0.9300	C20—O4	1.283 (4)
C4—C5	1.385 (5)	C20—C21	1.504 (5)
C4—C6	1.479 (5)	C21—C22	1.389 (6)
C5—N1	1.333 (4)	C21—C26	1.391 (6)
C5—H5	0.9300	C22—C23	1.376 (6)
C6—O10	1.233 (5)	C22—H22	0.9300
C6—N3	1.332 (5)	C23—C24	1.367 (9)
C7—N2	1.326 (5)	C23—H23	0.9300
C7—C8	1.386 (5)	C24—C25	1.374 (8)
C7—H7	0.9300	C24—H24	0.9300
C8—C9	1.377 (6)	C25—C26	1.402 (6)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.385 (6)	C26—O6	1.363 (5)
C9—H9	0.9300	N1—Co1	2.157 (3)
C10—C11	1.393 (5)	N2—Co1	2.147 (3)
C10—C12	1.499 (5)	N3—H3A	0.8600
C11—N2	1.337 (4)	N3—H3B	0.8600
C11—H11	0.9300	N4—H4A	0.8600
C12—O9	1.231 (5)	N4—H4B	0.8600
C12—N4	1.327 (5)	O1—Co1	2.112 (3)
C13—O3	1.248 (5)	O1—H1A	0.83 (5)
C13—O7	1.260 (5)	O1—H1B	0.81 (4)
C13—C14	1.512 (5)	O2—Co1	2.121 (3)
C14—C19	1.393 (6)	O2—H2A	0.834 (19)
C14—C15	1.399 (5)	O2—H2B	0.82 (4)
C15—C16	1.371 (6)	O3—Co1	2.079 (3)
C15—H15	0.9300	O4—Co1	2.076 (3)
C16—C17	1.376 (7)	O6—H6	0.8200
C16—H16	0.9300	O8—H8A	0.8200
N1—C1—C2	122.8 (4)	O5—C20—C21	121.0 (3)
N1—C1—H1	118.6	O4—C20—C21	115.2 (3)
C2—C1—H1	118.6	C22—C21—C26	118.8 (4)
C1—C2—C3	118.9 (4)	C22—C21—C20	119.9 (4)
C1—C2—H2	120.6	C26—C21—C20	121.3 (3)
C3—C2—H2	120.6	C23—C22—C21	121.1 (5)
C4—C3—C2	119.1 (4)	C23—C22—H22	119.5
C4—C3—H3	120.5	C21—C22—H22	119.5
C2—C3—H3	120.5	C24—C23—C22	119.6 (5)
C3—C4—C5	118.0 (3)	C24—C23—H23	120.2
C3—C4—C6	125.0 (3)	C22—C23—H23	120.2
C5—C4—C6	116.9 (4)	C23—C24—C25	121.1 (4)
N1—C5—C4	123.3 (4)	C23—C24—H24	119.4
N1—C5—H5	118.4	C25—C24—H24	119.4
C4—C5—H5	118.4	C24—C25—C26	119.4 (5)
O10—C6—N3	120.3 (4)	C24—C25—H25	120.3
O10—C6—C4	121.0 (3)	C26—C25—H25	120.3
N3—C6—C4	118.7 (4)	O6—C26—C21	123.0 (4)
N2—C7—C8	122.8 (3)	O6—C26—C25	117.1 (4)
N2—C7—H7	118.6	C21—C26—C25	119.9 (4)
C8—C7—H7	118.6	C5—N1—C1	117.9 (3)
C9—C8—C7	118.7 (4)	C5—N1—Co1	120.6 (3)
C9—C8—H8	120.7	C1—N1—Co1	121.5 (2)
C7—C8—H8	120.7	C7—N2—C11	118.3 (3)
C8—C9—C10	119.5 (3)	C7—N2—Co1	122.4 (2)
C8—C9—H9	120.3	C11—N2—Co1	119.2 (3)
C10—C9—H9	120.3	C6—N3—H3A	120.0
C9—C10—C11	117.7 (3)	C6—N3—H3B	120.0
C9—C10—C12	125.3 (3)	H3A—N3—H3B	120.0
C11—C10—C12	117.0 (4)	C12—N4—H4A	120.0
N2—C11—C10	123.0 (4)	C12—N4—H4B	120.0
N2—C11—H11	118.5	H4A—N4—H4B	120.0
C10—C11—H11	118.5	Co1—O1—H1A	134 (4)
O9—C12—N4	121.9 (3)	Co1—O1—H1B	105 (3)
O9—C12—C10	120.3 (3)	H1A—O1—H1B	106 (3)
N4—C12—C10	117.7 (4)	Co1—O2—H2A	103 (4)
O3—C13—O7	124.7 (3)	Co1—O2—H2B	142 (4)
O3—C13—C14	117.7 (3)	H2A—O2—H2B	105 (3)
O7—C13—C14	117.5 (4)	C13—O3—Co1	130.1 (3)
C19—C14—C15	118.7 (4)	C20—O4—Co1	134.1 (3)
C19—C14—C13	121.1 (4)	C26—O6—H6	109.5
C15—C14—C13	120.2 (3)	C19—O8—H8A	109.5
C16—C15—C14	121.0 (4)	O4—Co1—O3	174.58 (11)
C16—C15—H15	119.5	O4—Co1—O1	85.72 (12)
C14—C15—H15	119.5	O3—Co1—O1	90.40 (12)
C15—C16—C17	119.3 (5)	O4—Co1—O2	94.12 (12)
C15—C16—H16	120.3	O3—Co1—O2	90.11 (12)
C17—C16—H16	120.3	O1—Co1—O2	174.40 (12)
C18—C17—C16	121.4 (4)	O4—Co1—N2	88.92 (11)
C18—C17—H17	119.3	O3—Co1—N2	87.38 (11)
C16—C17—H17	119.3	O1—Co1—N2	91.06 (11)
C17—C18—C19	119.8 (4)	O2—Co1—N2	94.53 (12)
C17—C18—H18	120.1	O4—Co1—N1	92.82 (11)
C19—C18—H18	120.1	O3—Co1—N1	90.90 (11)
O8—C19—C14	122.1 (4)	O1—Co1—N1	89.14 (12)
O8—C19—C18	118.2 (4)	O2—Co1—N1	85.28 (13)
C14—C19—C18	119.7 (4)	N2—Co1—N1	178.26 (12)
O5—C20—O4	123.7 (3)
N1—C1—C2—C3	−0.8 (7)	C23—C24—C25—C26	1.0 (8)
C1—C2—C3—C4	−0.6 (7)	C22—C21—C26—O6	176.7 (4)
C2—C3—C4—C5	2.0 (7)	C20—C21—C26—O6	−2.3 (6)
C2—C3—C4—C6	−178.2 (4)	C22—C21—C26—C25	0.1 (6)
C3—C4—C5—N1	−2.2 (6)	C20—C21—C26—C25	−178.9 (4)
C6—C4—C5—N1	177.9 (4)	C24—C25—C26—O6	−177.1 (5)
C3—C4—C6—O10	−173.1 (4)	C24—C25—C26—C21	−0.4 (7)
C5—C4—C6—O10	6.7 (6)	C4—C5—N1—C1	0.9 (6)
C3—C4—C6—N3	8.4 (7)	C4—C5—N1—Co1	179.4 (3)
C5—C4—C6—N3	−171.7 (4)	C2—C1—N1—C5	0.6 (6)
N2—C7—C8—C9	−0.3 (7)	C2—C1—N1—Co1	−177.8 (4)
C7—C8—C9—C10	−0.3 (7)	C8—C7—N2—C11	1.1 (6)
C8—C9—C10—C11	0.2 (6)	C8—C7—N2—Co1	−173.8 (3)
C8—C9—C10—C12	179.5 (4)	C10—C11—N2—C7	−1.2 (6)
C9—C10—C11—N2	0.6 (6)	C10—C11—N2—Co1	173.9 (3)
C12—C10—C11—N2	−178.7 (4)	O7—C13—O3—Co1	−18.6 (6)
C9—C10—C12—O9	−170.9 (4)	C14—C13—O3—Co1	160.2 (3)
C11—C10—C12—O9	8.4 (6)	O5—C20—O4—Co1	−23.3 (6)
C9—C10—C12—N4	6.4 (6)	C21—C20—O4—Co1	154.5 (2)
C11—C10—C12—N4	−174.3 (4)	C20—O4—Co1—O1	−161.6 (3)
O3—C13—C14—C19	179.0 (4)	C20—O4—Co1—O2	12.8 (3)
O7—C13—C14—C19	−2.0 (6)	C20—O4—Co1—N2	107.2 (3)
O3—C13—C14—C15	−1.8 (6)	C20—O4—Co1—N1	−72.7 (3)
O7—C13—C14—C15	177.1 (4)	C13—O3—Co1—O1	166.1 (3)
C19—C14—C15—C16	2.3 (6)	C13—O3—Co1—O2	−8.3 (3)
C13—C14—C15—C16	−176.9 (4)	C13—O3—Co1—N2	−102.9 (3)
C14—C15—C16—C17	−1.5 (7)	C13—O3—Co1—N1	76.9 (3)
C15—C16—C17—C18	1.3 (7)	C7—N2—Co1—O4	−44.2 (3)
C16—C17—C18—C19	−1.9 (7)	C11—N2—Co1—O4	140.9 (3)
C15—C14—C19—O8	178.8 (4)	C7—N2—Co1—O3	139.7 (3)
C13—C14—C19—O8	−2.0 (7)	C11—N2—Co1—O3	−35.1 (3)
C15—C14—C19—C18	−2.9 (6)	C7—N2—Co1—O1	−129.9 (3)
C13—C14—C19—C18	176.4 (4)	C11—N2—Co1—O1	55.2 (3)
C17—C18—C19—O8	−178.9 (5)	C7—N2—Co1—O2	49.8 (3)
C17—C18—C19—C14	2.7 (7)	C11—N2—Co1—O2	−125.0 (3)
O5—C20—C21—C22	3.1 (6)	C5—N1—Co1—O4	39.2 (3)
O4—C20—C21—C22	−174.7 (4)	C1—N1—Co1—O4	−142.3 (3)
O5—C20—C21—C26	−177.9 (4)	C5—N1—Co1—O3	−144.7 (3)
O4—C20—C21—C26	4.3 (5)	C1—N1—Co1—O3	33.7 (3)
C26—C21—C22—C23	−0.5 (7)	C5—N1—Co1—O1	124.9 (3)
C20—C21—C22—C23	178.5 (4)	C1—N1—Co1—O1	−56.7 (3)
C21—C22—C23—C24	1.2 (8)	C5—N1—Co1—O2	−54.7 (3)
C22—C23—C24—C25	−1.4 (8)	C1—N1—Co1—O2	123.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O9^i	0.86	2.11	2.955 (4)	167
N4—H4A···O10^ii	0.86	2.09	2.916 (5)	162
N4—H4B···O6^iii	0.86	2.48	3.210 (6)	144
O6—H6···O4	0.82	1.80	2.521 (4)	146
O8—H8A···O7	0.82	1.83	2.553 (5)	147
O1—H1A···O5^iv	0.83 (5)	1.86 (5)	2.684 (4)	172 (5)
O1—H1B···O10^iv	0.81 (4)	2.11 (4)	2.810 (4)	145 (5)
O2—H2A···O7	0.83 (2)	1.88 (2)	2.677 (5)	158 (5)
O2—H2B···O9^v	0.82 (4)	2.23 (4)	2.906 (4)	140 (5)
C18—H18···O5^vi	0.93	2.41	3.311 (6)	165
C3—H3···Cg1^vii	0.93	2.68	3.520 (4)	151
C9—H9···Cg2^iii	0.93	2.82	3.614 (4)	144

Symmetry codes: (i) x−1, y, z+1; (ii) x+1, y, z−1; (iii) x, y, z−1; (iv) x+1, y, z; (v) x−1, y, z; (vi) −x, y−1/2, −z; (vii) x, y, z+1.