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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m826–m827.
Published online 2009 June 27. doi:  10.1107/S1600536809021837
PMCID: PMC2969222

Hydroxonium creatininium bis­(pyridine-2,6-dicarboxyl­ato-κ3 O 2,N,O 6)cobaltate(II) trihydrate

Abstract

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, π–π stacking inter­actions [centroid–centroid distances = 3.565 (14) and 3.425 (14) Å] and O(...)π inter­actions [O(...)centroid distance = 3.480 (2) Å] connect the various components in the crystal structure.

Related literature

For related structures, see: Aghabozorg, Derikvand et al. (2008 [triangle]); Aghabozorg, Ramezanipour et al. (2008 [triangle]); Moghimi et al. (2004 [triangle], 2005 [triangle]). For a review article on proton-transfer agents and their metal complexes, see: Aghabozorg, Manteghi et al. (2008 [triangle]). For the isotypic Ni compound, see: Attar Gharamaleki et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m826-scheme1.jpg

Experimental

Crystal data

  • (C4H8N3O)(H3O)[Co(C7H3NO4)2]·3H2O
  • M r = 576.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m826-efi1.jpg
  • a = 8.0937 (10) Å
  • b = 10.7389 (13) Å
  • c = 13.5976 (17) Å
  • α = 104.811 (2)°
  • β = 90.267 (2)°
  • γ = 92.415 (1)°
  • V = 1141.4 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.83 mm−1
  • T = 120 K
  • 0.18 × 0.12 × 0.09 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.889, T max = 0.930
  • 11652 measured reflections
  • 5488 independent reflections
  • 4149 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.097
  • S = 1.02
  • 5488 reflections
  • 335 parameters
  • H-atom parameters constrained
  • Δρmax = 0.77 e Å−3
  • Δρmin = −0.45 e Å−3

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021837/hy2201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021837/hy2201Isup2.hkl

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

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Packing diagram of the title compound. Hydrogen bonds are shown by dashed lines.
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) ...

Crystal data

(C4H8N3O)(H3O)[Co(C7H3NO4)2]·3H2OZ = 2
Mr = 576.34F(000) = 594
Triclinic, P1Dx = 1.677 Mg m3
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 mm1
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

Bruker SMART 1000 CCD diffractometer5488 independent reflections
Radiation source: fine-focus sealed tube4149 reflections with I > 2σ(I)
graphiteRint = 0.025
[var phi] 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

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 = 1.02w = 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 Å3
0 restraintsΔρmin = −0.45 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2201).

References

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