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Acta Cryst. (2009). E65, m826-m827    [ doi:10.1107/S1600536809021837 ]

Hydroxonium creatininium bis(pyridine-2,6-dicarboxylato-[kappa]3O2,N,O6)cobaltate(II) trihydrate

H. Aghabozorg, Z. Derikvand, J. Attar Gharamaleki and M. Yousefi

Abstract top

The title compound, (C4H8N3O)(H3O)[Co(C7H3NO4)2]·3H2O, contains a protonated creatininium cation, a hydroxonium (H3O)+ cation, a [Co(pydc)2]2- (pydcH2 = pyridine-2,6-dicarboxylic acid) complex anion, and three uncoordinated water molecules. The CoII atom is coordinated by four O and two N atoms from two pydc ligands in a distorted octahedral environment. The structure also contains three uncoordinated water molecules. Extensive intermolecular O-H...O, N-H...O and C-H...O hydrogen bonds, [pi]-[pi] stacking interactions [centroid-centroid distances = 3.565 (14) and 3.425 (14) Å] and O...[pi] interactions [O...centroid distance = 3.480 (2) Å] connect the various components in the crystal structure.

Comment top

We have previously reported some compounds containing creatinine (creat), pyridine-2,6-dicarboxylic acid (pydcH2) and various metals, such as (creatH)(pydcH).H2O (Moghimi et al., 2004), (creatH)2[Bi(pydc)2]2.4H2O (Moghimi et al., 2005), (creatH)[Zn(pydc)(pydcH)].4H2O (Aghabozorg, Ramezanipour et al., 2008) and (creatH)[Cr(pydc)2](pydcH2).6H2O (Aghabozorg, Derikvand et al., 2008). For more details and related literature see our recent review article (Aghabozorg, Manteghi et al., 2008).

We describe here the crystal structure of the title compound. The compound contains a [Co(pydc)2]2- anion, a (creatH)+ and a (H3O)+ cation, and three uncoordinated water molecules (Fig. 1). In the anion, the CoII atom is six-coordinated by two N atoms (N1 and N2) and four O atoms (O1, O4, O5 and O8) from the carboxylate groups of two (pydc)2- ligands, with the bond length range of 2.029 (2)–2.2239 (19) Å (Table 1). The N1—Co1—N2 [171.90 (8)°], O8—Co1—O5 [151.26 (7)°] and O4—Co1—O1 [152.09 (7)°] angles show that the four carboxylate groups of the two (pydc)2- ligands orient in a flattened tetrahedral arrangement around the central atom. The coordination environment around CoII is distorted octahedral. The O8—Co1—O4—C7 and O1—Co1—O8—C14 torsion angles are -95.15 (17)° and 95.48 (19)°, respectively, thus it can be concluded that two (pydc)2- ligands are almost perpendicular to each other. The intermolecular forces in the structure could be divided in three main branches, ionic interactions which gather principal anionic complex and counter cation together, X—H···O hydrogen bonds (Fig. 2 and Table 2), where X= O, N, C, and O···π, π–π stacking interactions. The π–π stacking interactions between the pyridyl rings, with centroid–centroid distances of 3.565 (14) and 3.425 (14) Å, and the O···π interaction between the carboxylate O atom and pyridyl ring, with an O···centroid distance of 3.480 (2)Å are observed (Fig. 3). Ion pairing, π–π stacking interactions and extensive intermolecular hydrogen bonds connected the various components into a supramolecular structure.

Related literature top

For related structures, see: Aghabozorg, Derikvand et al. (2008); Aghabozorg, Ramezanipour et al. (2008); Moghimi et al. (2004, 2005). For a review article, see: Aghabozorg, Manteghi et al. (2008). For the isotypic Ni compound, see: Attar Gharamaleki et al. (2009).

Experimental top

The reaction between pyridine-2,6-dicarboxylic acid (100 mg, 1 mmol) in 10 ml water, cratinine (110 mg, 1 mmol) in 20 ml water and Co(NO3)2.6H2O (87 mg, 0.5 mmol) in 5 ml water at a 2:2:1 molar ratio gave a red compound after slow evaporation of the solvent at the room temperature. The crystals obtained were stable in air.

Refinement top

H atoms on O and N atoms were found from difference Fourier maps. H atoms on C atoms were positioned geometrically. All H atoms were refined in riding models, with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N) or 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound. Hydrogen bonds are shown by dashed lines.
[Figure 3] Fig. 3. The π–π and O···π stacking interactions in the title compound. The centroid–centroid distances are 3.425 (14) Å between Cg1 (N1, C2–C6) and Cg1i, and 3.565 (14) Å between Cg2ii (N2ii, C9ii–C13ii) and Cg2iii. The O7···Cg2iii distance is 3.480 (2) Å. [Symmetry codes: (i) 1-x, 2-y, 1-z; (ii) 1+x, y, z; (iii) 1-x, 2-y, -z.]
Hydroxonium creatininium bis(pyridine-2,6-dicarboxylato-κ3O2,N,O6)cobaltate(II) trihydrate top
Crystal data top
(C4H8N3O)(H3O)[Co(C7H3NO4)2]·3H2OZ = 2
Mr = 576.34F(000) = 594
Triclinic, P1Dx = 1.677 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0937 (10) ÅCell parameters from 843 reflections
b = 10.7389 (13) Åθ = 3–27°
c = 13.5976 (17) ŵ = 0.83 mm−1
α = 104.811 (2)°T = 120 K
β = 90.267 (2)°Prism, red
γ = 92.415 (1)°0.18 × 0.12 × 0.09 mm
V = 1141.4 (2) Å3
Data collection top
Bruker SMART 1000 CCD
diffractometer		5488 independent reflections
Radiation source: fine-focus sealed tube4149 reflections with I > 2σ(I)
graphiteRint = 0.025
φ and ω scansθmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→10
Tmin = 0.889, Tmax = 0.930k = −14→14
11652 measured reflectionsl = −17→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: mixed
wR(F2) = 0.097H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.015P)2 + 2.6P]
where P = (Fo2 + 2Fc2)/3
5488 reflections(Δ/σ)max < 0.001
335 parametersΔρmax = 0.77 e Å−3
0 restraintsΔρmin = −0.45 e Å−3
Crystal data top
(C4H8N3O)(H3O)[Co(C7H3NO4)2]·3H2Oγ = 92.415 (1)°
Mr = 576.34V = 1141.4 (2) Å3
Triclinic, P1Z = 2
a = 8.0937 (10) ÅMo Kα radiation
b = 10.7389 (13) ŵ = 0.83 mm−1
c = 13.5976 (17) ÅT = 120 K
α = 104.811 (2)°0.18 × 0.12 × 0.09 mm
β = 90.267 (2)°
Data collection top
Bruker SMART 1000 CCD
diffractometer		5488 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4149 reflections with I > 2σ(I)
Tmin = 0.889, Tmax = 0.930Rint = 0.025
11652 measured reflectionsθmax = 28.0°
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.097Δρmax = 0.77 e Å−3
S = 1.02Δρmin = −0.45 e Å−3
5488 reflectionsAbsolute structure: ?
335 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.26506 (4)0.93000 (3)0.23131 (3)0.01942 (10)
O10.4562 (2)0.78341 (18)0.19033 (13)0.0230 (4)
O20.6104 (2)0.65616 (18)0.25814 (14)0.0252 (4)
O30.0940 (2)1.13617 (18)0.50661 (14)0.0254 (4)
O40.1083 (2)1.04931 (18)0.33852 (13)0.0232 (4)
O50.0722 (2)0.78287 (17)0.16490 (13)0.0220 (4)
O6−0.0601 (2)0.69039 (18)0.01715 (13)0.0249 (4)
O70.4810 (2)1.23340 (18)0.13445 (13)0.0238 (4)
O80.4131 (2)1.09779 (18)0.22942 (13)0.0241 (4)
O90.2979 (2)0.47606 (19)0.53766 (14)0.0287 (4)
N10.3283 (2)0.89101 (19)0.36453 (15)0.0161 (4)
N20.2268 (2)0.9517 (2)0.08903 (15)0.0170 (4)
N30.1336 (3)0.5901 (2)0.45644 (15)0.0181 (4)
H3A0.08010.63460.50910.022*
N40.2130 (3)0.5206 (2)0.29648 (16)0.0202 (4)
N50.0027 (3)0.6690 (2)0.33142 (15)0.0210 (5)
H5A−0.00740.67030.26720.025*
H5B−0.06020.71650.37760.025*
C10.5092 (3)0.7418 (2)0.26371 (18)0.0188 (5)
C20.4403 (3)0.8035 (2)0.36658 (19)0.0180 (5)
C30.4860 (3)0.7762 (2)0.45730 (19)0.0198 (5)
H3B0.56600.71430.45840.024*
C40.4112 (3)0.8422 (2)0.54679 (19)0.0203 (5)
H4A0.43820.82450.60980.024*
C50.2971 (3)0.9341 (2)0.54291 (19)0.0206 (5)
H5C0.24600.98070.60310.025*
C60.2589 (3)0.9566 (2)0.44902 (18)0.0174 (5)
C70.1427 (3)1.0555 (2)0.43192 (19)0.0190 (5)
C80.0403 (3)0.7707 (2)0.07148 (18)0.0191 (5)
C90.1295 (3)0.8660 (2)0.02324 (18)0.0177 (5)
C100.1127 (3)0.8709 (3)−0.07723 (19)0.0201 (5)
H10A0.04470.8087−0.12400.024*
C110.1983 (3)0.9690 (3)−0.10736 (19)0.0222 (5)
H11A0.18960.9743−0.17590.027*
C120.2966 (3)1.0597 (3)−0.03808 (19)0.0200 (5)
H12A0.35381.1283−0.05780.024*
C130.3090 (3)1.0472 (2)0.06107 (19)0.0180 (5)
C140.4103 (3)1.1339 (2)0.14799 (19)0.0199 (5)
C150.1105 (3)0.5968 (2)0.35806 (18)0.0182 (5)
C160.3147 (3)0.4547 (3)0.35453 (19)0.0221 (5)
H16A0.43360.47830.35050.027*
H16B0.29760.35990.33030.027*
C170.2520 (3)0.5040 (3)0.4611 (2)0.0213 (5)
C180.2037 (4)0.4869 (3)0.18563 (19)0.0279 (6)
H18A0.21950.56520.16170.042*
H18B0.09510.44570.16270.042*
H18C0.29030.42720.15800.042*
O1W−0.0036 (2)0.29618 (18)0.36045 (14)0.0249 (4)
H10.01620.21660.34760.037*
H2−0.08560.30080.32250.037*
O2W0.7786 (2)0.55028 (19)0.10484 (14)0.0293 (4)
H30.72690.49120.06030.044*
H40.82320.60100.07280.044*
H50.71150.59070.14810.044*
O3W0.7461 (3)0.3583 (2)0.25576 (16)0.0362 (5)
H60.65880.32360.22350.054*
H70.72400.42840.29830.054*
O4W0.3941 (3)0.6406 (2)−0.00313 (15)0.0468 (7)
H80.43360.6891−0.03860.070*
H90.41220.67820.05920.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02341 (19)0.02192 (19)0.01396 (17)0.00133 (14)−0.00051 (13)0.00646 (13)
O10.0280 (10)0.0275 (10)0.0147 (9)0.0058 (8)0.0015 (7)0.0067 (7)
O20.0268 (10)0.0296 (10)0.0195 (9)0.0106 (8)0.0029 (8)0.0051 (8)
O30.0299 (10)0.0242 (10)0.0208 (9)0.0052 (8)0.0040 (8)0.0027 (8)
O40.0289 (10)0.0246 (10)0.0173 (9)0.0063 (8)0.0022 (7)0.0065 (7)
O50.0269 (10)0.0249 (10)0.0152 (9)−0.0037 (8)−0.0011 (7)0.0075 (7)
O60.0303 (10)0.0264 (10)0.0168 (9)−0.0080 (8)−0.0021 (8)0.0048 (8)
O70.0279 (10)0.0247 (10)0.0197 (9)−0.0077 (8)−0.0030 (8)0.0091 (8)
O80.0328 (10)0.0253 (10)0.0155 (9)−0.0052 (8)−0.0017 (8)0.0086 (7)
O90.0327 (11)0.0354 (11)0.0201 (9)0.0093 (9)−0.0025 (8)0.0100 (8)
N10.0173 (10)0.0173 (10)0.0136 (9)−0.0022 (8)0.0000 (8)0.0042 (8)
N20.0173 (10)0.0195 (11)0.0142 (10)0.0018 (8)−0.0002 (8)0.0043 (8)
N30.0199 (10)0.0216 (11)0.0133 (10)0.0024 (8)0.0011 (8)0.0050 (8)
N40.0224 (11)0.0230 (11)0.0153 (10)0.0054 (9)−0.0002 (8)0.0047 (9)
N50.0255 (11)0.0262 (12)0.0116 (10)0.0025 (9)0.0010 (8)0.0051 (9)
C10.0199 (12)0.0205 (13)0.0150 (11)−0.0018 (10)−0.0008 (9)0.0033 (10)
C20.0167 (12)0.0184 (12)0.0179 (12)−0.0009 (9)0.0010 (9)0.0035 (10)
C30.0193 (12)0.0214 (13)0.0193 (12)−0.0009 (10)−0.0028 (10)0.0067 (10)
C40.0242 (13)0.0231 (13)0.0141 (11)−0.0049 (10)−0.0038 (10)0.0067 (10)
C50.0227 (13)0.0231 (13)0.0141 (12)−0.0035 (10)0.0020 (10)0.0021 (10)
C60.0172 (12)0.0178 (12)0.0165 (12)−0.0023 (9)0.0003 (9)0.0037 (10)
C70.0180 (12)0.0178 (12)0.0219 (12)0.0009 (10)0.0031 (10)0.0062 (10)
C80.0210 (12)0.0194 (12)0.0166 (12)0.0011 (10)0.0013 (10)0.0039 (10)
C90.0185 (12)0.0175 (12)0.0171 (12)0.0023 (10)0.0020 (9)0.0042 (10)
C100.0187 (12)0.0246 (13)0.0155 (12)0.0009 (10)−0.0006 (9)0.0028 (10)
C110.0250 (13)0.0286 (14)0.0143 (12)0.0030 (11)0.0002 (10)0.0074 (10)
C120.0188 (12)0.0238 (13)0.0193 (12)0.0036 (10)0.0032 (10)0.0087 (10)
C130.0160 (12)0.0194 (12)0.0201 (12)0.0037 (9)0.0018 (9)0.0074 (10)
C140.0180 (12)0.0239 (13)0.0181 (12)0.0014 (10)0.0003 (10)0.0059 (10)
C150.0194 (12)0.0185 (12)0.0158 (12)−0.0035 (10)0.0001 (9)0.0031 (10)
C160.0225 (13)0.0246 (13)0.0195 (12)0.0042 (11)−0.0009 (10)0.0056 (10)
C170.0197 (12)0.0216 (13)0.0227 (13)0.0003 (10)−0.0019 (10)0.0062 (10)
C180.0381 (16)0.0293 (15)0.0149 (12)0.0067 (12)0.0010 (11)0.0024 (11)
O1W0.0284 (10)0.0249 (10)0.0216 (9)0.0065 (8)−0.0015 (8)0.0052 (8)
O2W0.0354 (11)0.0256 (10)0.0246 (10)−0.0025 (9)0.0084 (8)0.0027 (8)
O3W0.0351 (12)0.0370 (12)0.0304 (11)0.0082 (10)−0.0113 (9)−0.0037 (9)
O4W0.0845 (19)0.0357 (13)0.0170 (10)−0.0282 (12)0.0008 (11)0.0061 (9)
Geometric parameters (Å, °) top
Co1—N12.029 (2)C3—H3B0.9500
Co1—N22.031 (2)C4—C51.390 (4)
Co1—O82.1273 (18)C4—H4A0.9500
Co1—O42.1389 (18)C5—C61.394 (3)
Co1—O52.1904 (18)C5—H5C0.9500
Co1—O12.2239 (19)C6—C71.509 (3)
O1—C11.273 (3)C8—C91.511 (3)
O2—C11.245 (3)C9—C101.387 (3)
O3—C71.233 (3)C10—C111.386 (4)
O4—C71.283 (3)C10—H10A0.9500
O5—C81.268 (3)C11—C121.388 (4)
O6—C81.249 (3)C11—H11A0.9500
O7—C141.247 (3)C12—C131.392 (3)
O8—C141.263 (3)C12—H12A0.9500
O9—C171.215 (3)C13—C141.516 (3)
N1—C61.325 (3)C16—C171.509 (4)
N1—C21.338 (3)C16—H16A0.9900
N2—C91.334 (3)C16—H16B0.9900
N2—C131.335 (3)C18—H18A0.9800
N3—C151.370 (3)C18—H18B0.9800
N3—C171.371 (3)C18—H18C0.9800
N3—H3A0.8800O1W—H10.8500
N4—C151.331 (3)O1W—H20.8500
N4—C181.458 (3)O2W—H30.8500
N4—C161.459 (3)O2W—H40.8500
N5—C151.301 (3)O2W—H50.8500
N5—H5A0.8800O3W—H60.8500
N5—H5B0.8800O3W—H70.8500
C1—C21.507 (3)O4W—H80.8500
C2—C31.391 (3)O4W—H90.8500
C3—C41.397 (4)
N1—Co1—N2171.90 (8)N1—C6—C7113.5 (2)
N1—Co1—O8104.11 (7)C5—C6—C7125.5 (2)
N2—Co1—O876.44 (7)O3—C7—O4126.1 (2)
N1—Co1—O477.02 (8)O3—C7—C6118.5 (2)
N2—Co1—O4111.08 (8)O4—C7—C6115.4 (2)
O8—Co1—O488.59 (7)O6—C8—O5126.3 (2)
N1—Co1—O5104.55 (7)O6—C8—C9117.6 (2)
N2—Co1—O575.49 (7)O5—C8—C9116.1 (2)
O8—Co1—O5151.26 (7)N2—C9—C10121.4 (2)
O4—Co1—O595.77 (7)N2—C9—C8112.8 (2)
N1—Co1—O175.10 (7)C10—C9—C8125.8 (2)
N2—Co1—O196.82 (7)C11—C10—C9118.0 (2)
O8—Co1—O199.21 (7)C11—C10—H10A121.0
O4—Co1—O1152.09 (7)C9—C10—H10A121.0
O5—Co1—O190.12 (7)C10—C11—C12120.4 (2)
C1—O1—Co1115.11 (16)C10—C11—H11A119.8
C7—O4—Co1114.49 (16)C12—C11—H11A119.8
C8—O5—Co1115.09 (16)C11—C12—C13118.1 (2)
C14—O8—Co1116.51 (16)C11—C12—H12A121.0
C6—N1—C2121.3 (2)C13—C12—H12A121.0
C6—N1—Co1118.26 (17)N2—C13—C12120.9 (2)
C2—N1—Co1120.43 (16)N2—C13—C14112.3 (2)
C9—N2—C13121.1 (2)C12—C13—C14126.8 (2)
C9—N2—Co1119.81 (16)O7—C14—O8125.7 (2)
C13—N2—Co1118.89 (16)O7—C14—C13118.6 (2)
C15—N3—C17110.3 (2)O8—C14—C13115.6 (2)
C15—N3—H3A124.8N5—C15—N4126.3 (2)
C17—N3—H3A124.8N5—C15—N3123.3 (2)
C15—N4—C18125.2 (2)N4—C15—N3110.4 (2)
C15—N4—C16110.1 (2)N4—C16—C17102.3 (2)
C18—N4—C16123.7 (2)N4—C16—H16A111.3
C15—N5—H5A120.0C17—C16—H16A111.3
C15—N5—H5B120.0N4—C16—H16B111.3
H5A—N5—H5B120.0C17—C16—H16B111.3
O2—C1—O1126.4 (2)H16A—C16—H16B109.2
O2—C1—C2118.0 (2)O9—C17—N3125.7 (2)
O1—C1—C2115.6 (2)O9—C17—C16127.5 (2)
N1—C2—C3121.2 (2)N3—C17—C16106.8 (2)
N1—C2—C1113.7 (2)N4—C18—H18A109.5
C3—C2—C1125.1 (2)N4—C18—H18B109.5
C2—C3—C4118.3 (2)H18A—C18—H18B109.5
C2—C3—H3B120.9N4—C18—H18C109.5
C4—C3—H3B120.9H18A—C18—H18C109.5
C5—C4—C3119.4 (2)H18B—C18—H18C109.5
C5—C4—H4A120.3H1—O1W—H2105.5
C3—C4—H4A120.3H3—O2W—H4106.0
C4—C5—C6118.7 (2)H3—O2W—H5110.2
C4—C5—H5C120.6H4—O2W—H5109.9
C6—C5—H5C120.6H6—O3W—H7110.0
N1—C6—C5121.0 (2)H8—O4W—H9108.1
N1—Co1—O1—C12.34 (17)C2—N1—C6—C5−1.7 (4)
N2—Co1—O1—C1−178.09 (18)Co1—N1—C6—C5179.89 (18)
O8—Co1—O1—C1104.61 (18)C2—N1—C6—C7177.0 (2)
O4—Co1—O1—C10.0 (3)Co1—N1—C6—C7−1.4 (3)
O5—Co1—O1—C1−102.69 (18)C4—C5—C6—N10.7 (4)
N1—Co1—O4—C79.68 (17)C4—C5—C6—C7−177.8 (2)
N2—Co1—O4—C7−170.03 (17)Co1—O4—C7—O3164.3 (2)
O8—Co1—O4—C7−95.15 (17)Co1—O4—C7—C6−13.2 (3)
O5—Co1—O4—C7113.32 (17)N1—C6—C7—O3−167.8 (2)
O1—Co1—O4—C712.1 (3)C5—C6—C7—O310.9 (4)
N1—Co1—O5—C8−164.94 (17)N1—C6—C7—O410.0 (3)
N2—Co1—O5—C86.69 (17)C5—C6—C7—O4−171.4 (2)
O8—Co1—O5—C819.4 (3)Co1—O5—C8—O6177.3 (2)
O4—Co1—O5—C8117.01 (18)Co1—O5—C8—C9−4.7 (3)
O1—Co1—O5—C8−90.32 (18)C13—N2—C9—C101.5 (4)
N1—Co1—O8—C14172.30 (18)Co1—N2—C9—C10−173.89 (18)
N2—Co1—O8—C140.63 (18)C13—N2—C9—C8−176.7 (2)
O4—Co1—O8—C14−111.46 (19)Co1—N2—C9—C87.9 (3)
O5—Co1—O8—C14−12.0 (3)O6—C8—C9—N2176.6 (2)
O1—Co1—O8—C1495.48 (19)O5—C8—C9—N2−1.6 (3)
O8—Co1—N1—C681.22 (18)O6—C8—C9—C10−1.5 (4)
O4—Co1—N1—C6−3.96 (17)O5—C8—C9—C10−179.7 (2)
O5—Co1—N1—C6−96.65 (18)N2—C9—C10—C11−1.1 (4)
O1—Co1—N1—C6177.18 (19)C8—C9—C10—C11176.9 (2)
O8—Co1—N1—C2−97.19 (19)C9—C10—C11—C12−0.4 (4)
O4—Co1—N1—C2177.62 (19)C10—C11—C12—C131.3 (4)
O5—Co1—N1—C284.94 (19)C9—N2—C13—C12−0.5 (4)
O1—Co1—N1—C2−1.23 (17)Co1—N2—C13—C12174.95 (18)
O8—Co1—N2—C9178.3 (2)C9—N2—C13—C14179.3 (2)
O4—Co1—N2—C9−98.58 (19)Co1—N2—C13—C14−5.2 (3)
O5—Co1—N2—C9−7.92 (18)C11—C12—C13—N2−0.9 (4)
O1—Co1—N2—C980.44 (19)C11—C12—C13—C14179.3 (2)
O8—Co1—N2—C132.82 (17)Co1—O8—C14—O7175.7 (2)
O4—Co1—N2—C1385.92 (19)Co1—O8—C14—C13−3.5 (3)
O5—Co1—N2—C13176.59 (19)N2—C13—C14—O7−173.6 (2)
O1—Co1—N2—C13−95.06 (18)C12—C13—C14—O76.2 (4)
Co1—O1—C1—O2176.8 (2)N2—C13—C14—O85.6 (3)
Co1—O1—C1—C2−3.0 (3)C12—C13—C14—O8−174.6 (2)
C6—N1—C2—C31.2 (4)C18—N4—C15—N5−11.3 (4)
Co1—N1—C2—C3179.52 (18)C16—N4—C15—N5−179.8 (2)
C6—N1—C2—C1−178.2 (2)C18—N4—C15—N3168.9 (2)
Co1—N1—C2—C10.2 (3)C16—N4—C15—N30.4 (3)
O2—C1—C2—N1−177.8 (2)C17—N3—C15—N5178.5 (2)
O1—C1—C2—N12.0 (3)C17—N3—C15—N4−1.7 (3)
O2—C1—C2—C32.9 (4)C15—N4—C16—C170.9 (3)
O1—C1—C2—C3−177.4 (2)C18—N4—C16—C17−167.8 (2)
N1—C2—C3—C40.4 (4)C15—N3—C17—O9−179.0 (3)
C1—C2—C3—C4179.6 (2)C15—N3—C17—C162.2 (3)
C2—C3—C4—C5−1.3 (4)N4—C16—C17—O9179.4 (3)
C3—C4—C5—C60.8 (4)N4—C16—C17—N3−1.8 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O1Wi0.881.862.716 (3)164
N5—H5A···O50.882.152.882 (3)141
N5—H5B···O3ii0.881.962.764 (3)152
O1W—H1···O4iii0.851.952.782 (3)166
O1W—H2···O3Wiv0.851.852.673 (3)164
O2W—H3···O4Wv0.851.702.522 (3)163
O2W—H4···O6vi0.851.642.481 (3)170
O2W—H5···O20.851.712.537 (3)164
O3W—H6···O7iii0.851.932.778 (3)172
O3W—H7···O9vii0.852.222.948 (3)144
O4W—H8···O7viii0.851.842.680 (3)169
O4W—H9···O10.851.872.718 (3)172
C3—H3B···O9vii0.952.373.301 (3)165
C4—H4A···O8ix0.952.433.252 (3)145
C18—H18C···O7iii0.982.603.535 (4)160
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z; (vi) x+1, y, z; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y+2, −z; (ix) −x+1, −y+2, −z+1.
Table 1
Selected geometric parameters (Å) top
Co1—N12.029 (2)Co1—O42.1389 (18)
Co1—N22.031 (2)Co1—O52.1904 (18)
Co1—O82.1273 (18)Co1—O12.2239 (19)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O1Wi0.881.862.716 (3)164
N5—H5A···O50.882.152.882 (3)141
N5—H5B···O3ii0.881.962.764 (3)152
O1W—H1···O4iii0.851.952.782 (3)166
O1W—H2···O3Wiv0.851.852.673 (3)164
O2W—H3···O4Wv0.851.702.522 (3)163
O2W—H4···O6vi0.851.642.481 (3)170
O2W—H5···O20.851.712.537 (3)164
O3W—H6···O7iii0.851.932.778 (3)172
O3W—H7···O9vii0.852.222.948 (3)144
O4W—H8···O7viii0.851.842.680 (3)169
O4W—H9···O10.851.872.718 (3)172
C3—H3B···O9vii0.952.373.301 (3)165
C4—H4A···O8ix0.952.433.252 (3)145
C18—H18C···O7iii0.982.603.535 (4)160
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z; (vi) x+1, y, z; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y+2, −z; (ix) −x+1, −y+2, −z+1.
references
References top

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Moghimi, A., Sharif, M. A. & Aghabozorg, H. (2004). Acta Cryst. E60, o1790–o1792.

Moghimi, A., Sharif, M. A., Shokrollahi, A., Shamsipur, M. & Aghabozorg, H. (2005). Z. Anorg. Allg. Chem. 631, 902–908.

Sheldrick, G. M. (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.