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Acta Cryst. (2007). E63, m2554    [ doi:10.1107/S1600536807045229 ]

Bis[3-(4-carboxyphenoxy)propionato-[kappa]O]bis[3-(4-carboxyphenoxy)propionic acid-[kappa]O]bis(pyridine-[kappa]N)cobalt(II)

L.-L. Kong, S. Gao and L.-H. Huo

Abstract top

The title complex, [Co(C10H9O5)2(C10H10O5)2(C5H5N)2], is a neutral mononuclear complex. The CoII atom, which lies on a centre of symmetry, has a distorted octahedral geometry involving two O atoms of the 3-(4-carboxyphenoxy)propionate groups, two O atoms of the 3-(4-carboxyphenoxy)propionic acid groups and two N atoms of two pyridine ligands. A two-dimensional supramolecular structure is constructed via [pi]-[pi] interactions [centroid-to-centroid distance 3.589 (3) Å] and hydrogen-bonding interactions.

Comment top

Our studies have addressed the metal derivatives of carboxyphenoxypropionic acids. 3-(4-carboxylatophenoxy)propionic acid [3-(p-CPOPH2)] is a potential flexible multidentated ligand which could be used as a terminal ligand or a bridging ligand with different coordination modes when coordinated to various metal ions. In addition to its versatile coordination modes, 3-(4-carboxylatophenoxy)propionic acid may take part in hydrogen-bonding interactions by functioning as either a hydrogen-bond donor or acceptor (Gao & Ng, 2006). Recently, we have reported the structure of a dinuclear cobalt(II) complex incorporating 3-(4-carboxylatophenoxy)propionate groups, namely [Co2(C10H8O5)2(H2O)8]·4H2O, (I) (Xiao et al., 2006).

In contrast to (I), the title compound is a mononuclear complex (Fig. 1), in which the Co atom lies on a centre of symmetry and displays a distorted octahedral geometry involving two O atoms of the 3-(4-carboxylatophenoxy)propionate groups, two O atoms of the 3-(4-carboxyphenoxy)propionic acid groups and two N atoms of two pyridine ligands. The average Co—O(carbonyl) bond length is 2.094 (2) Å, which is somewhat longer than the corresponding value in (I), 2.038 (3) Å. Furthermore, a two-dimensional supramolecular layer is constructed via π–π stacking interactions between the pyridine rings [centroid-centroid distance: 3.589 (3) Å] and hydrogen-bonding interactions (Table 2). There is, in additiom, a strong intramolecular H-bond (first entry in Table 2 and Fig. 1), linking the two independent, coordinated carboxylate groups.

Related literature top

3-(4-Carboxyphenoxy)propionic acid [3-(p-CPOPH2)] has been reported previously (Gao & Ng, 2006). In our previous work, the cobalt(II) complex of 3-(p-CPOPH2) has been characterized by X-ray crystallography (Xiao et al., 2006).

Experimental top

The title complex was prepared by the addition of cobalt(II) acetate trihydrate (10 mmol), pyridine (1 ml) and 3-(p-CPOPH2) (15 mmol) to a H2O/MeOH (v/v = 1:1) solution. Red crystals were obtained from the filtered solution at room temperature over several days. CH&N analysis. Calc. for C50H48N2O20Co: C 56.88, H 4.58, N 2.65%. Found: C 56.89, H 4.56, N 2.66%.

Refinement top

The H atoms were placed in calculated positions with C—H = 0.93 or 0.97 Å and Uiso(H) = 1.2Ueq (C) and were included in the refinement in the riding model approximation. The H atoms of hydroxyl groups were located in difference Fourier maps and refined with the O—H distance restrained to 0.85 (1) Å and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with 30% probability ellipsoid for the non-H atoms. Dashed lines indicate O—H···O hydrogen bonds. [Symmetry code: (i) −x + 1,-y + 1,-z]
Bis[3-(4-carboxyphenoxy)propionato-κO]bis[3- (4-carboxyphenoxy)propionic acid-κO]bis(pyridine-κN)cobalt(II) top
Crystal data top
[Co(C10H9O5)2(C10H10O5)2(C5H5N)2]Z = 1
Mr = 1055.83F000 = 549
Triclinic, P1Dx = 1.483 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.2621 (17) ÅCell parameters from 7199 reflections
b = 8.7358 (17) Åθ = 3.1–27.4º
c = 17.502 (4) ŵ = 0.45 mm−1
α = 76.58 (3)ºT = 295 (2) K
β = 76.53 (3)ºBlock, red
γ = 78.94 (3)º0.38 × 0.25 × 0.19 mm
V = 1182.2 (5) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5356 independent reflections
Radiation source: fine-focus sealed tube2748 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
Detector resolution: 10 pixels mm-1θmax = 27.5º
T = 295(2) Kθmin = 3.1º
ω scansh = −10→10
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −11→11
Tmin = 0.848, Tmax = 0.920l = −22→22
11688 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.215  w = 1/[σ2(Fo2) + (0.116P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
5356 reflectionsΔρmax = 0.52 e Å−3
341 parametersΔρmin = −0.98 e Å−3
3 restraintsExtinction correction: SHELXL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (3)
Crystal data top
[Co(C10H9O5)2(C10H10O5)2(C5H5N)2]γ = 78.94 (3)º
Mr = 1055.83V = 1182.2 (5) Å3
Triclinic, P1Z = 1
a = 8.2621 (17) ÅMo Kα
b = 8.7358 (17) ŵ = 0.45 mm−1
c = 17.502 (4) ÅT = 295 (2) K
α = 76.58 (3)º0.38 × 0.25 × 0.19 mm
β = 76.53 (3)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5356 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2748 reflections with I > 2σ(I)
Tmin = 0.848, Tmax = 0.920Rint = 0.038
11688 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0563 restraints
wR(F2) = 0.215H atoms treated by a mixture of
independent and constrained refinement
S = 1.07Δρmax = 0.52 e Å−3
5356 reflectionsΔρmin = −0.98 e Å−3
341 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
Co10.50000.50000.00000.0479 (3)
O10.5675 (4)0.1351 (3)0.13958 (16)0.0678 (8)
O20.5516 (4)0.3988 (3)0.11210 (15)0.0602 (7)
O30.2880 (3)0.1751 (3)0.29858 (16)0.0637 (7)
O4−0.1451 (4)−0.3393 (4)0.52659 (19)0.0735 (9)
H20−0.224 (5)−0.394 (6)0.551 (3)0.110*
O5−0.3392 (4)−0.1726 (4)0.46859 (19)0.0738 (8)
O60.3566 (4)0.6826 (3)0.05983 (17)0.0659 (8)
O70.3480 (5)0.9294 (4)−0.00646 (19)0.0822 (10)
H300.380 (8)0.906 (7)−0.0533 (16)0.123*
O80.0279 (3)0.8049 (3)0.19057 (16)0.0630 (7)
O9−0.4260 (4)0.3466 (4)0.45047 (19)0.0741 (9)
H10−0.509 (5)0.297 (6)0.474 (3)0.111*
O10−0.6187 (4)0.5077 (3)0.38703 (18)0.0680 (8)
N10.2787 (4)0.3899 (3)0.02698 (19)0.0514 (7)
C10.3358 (5)0.8248 (5)0.0582 (2)0.0536 (9)
C20.2917 (5)0.8889 (5)0.1345 (2)0.0619 (11)
H10.39460.90190.14840.074*
H20.22480.99310.12520.074*
C30.1959 (5)0.7840 (5)0.2039 (2)0.0606 (10)
H30.24680.67360.20660.073*
H40.19570.81420.25390.073*
C4−0.0854 (5)0.7190 (5)0.2447 (2)0.0553 (9)
C5−0.0460 (5)0.5970 (5)0.3068 (2)0.0616 (10)
H50.06410.56940.31470.074*
C6−0.1713 (5)0.5166 (5)0.3568 (2)0.0611 (10)
H6−0.14470.43520.39870.073*
C7−0.3353 (5)0.5547 (4)0.3459 (2)0.0546 (9)
C8−0.3740 (5)0.6792 (5)0.2833 (2)0.0612 (10)
H8−0.48430.70800.27560.073*
C9−0.2496 (5)0.7586 (5)0.2333 (2)0.0613 (10)
H9−0.27570.83990.19130.074*
C10−0.4689 (5)0.4657 (5)0.3978 (2)0.0576 (10)
C110.5552 (4)0.2669 (5)0.1590 (2)0.0516 (9)
C120.5483 (6)0.2669 (5)0.2461 (2)0.0660 (11)
H110.66230.25500.25460.079*
H120.49090.36920.25760.079*
C130.4605 (5)0.1377 (5)0.3044 (2)0.0625 (11)
H130.50770.03480.29060.075*
H140.47290.13490.35850.075*
C140.1814 (5)0.0733 (4)0.3434 (2)0.0531 (9)
C150.2274 (5)−0.0672 (5)0.3948 (2)0.0572 (10)
H150.3389−0.09800.40030.069*
C160.1063 (5)−0.1611 (5)0.4377 (2)0.0568 (10)
H160.1377−0.25560.47170.068*
C17−0.0601 (5)−0.1172 (4)0.4310 (2)0.0536 (9)
C18−0.1041 (5)0.0249 (5)0.3791 (3)0.0658 (11)
H18−0.21560.05660.37360.079*
C190.0148 (5)0.1173 (5)0.3365 (3)0.0658 (11)
H19−0.01660.21150.30220.079*
C20−0.1901 (5)−0.2154 (5)0.4776 (2)0.0549 (9)
C210.2354 (5)0.3318 (5)−0.0281 (3)0.0614 (10)
H210.30720.3351−0.07780.074*
C220.0891 (6)0.2669 (5)−0.0151 (3)0.0723 (12)
H220.06410.2259−0.05480.087*
C23−0.0170 (6)0.2644 (6)0.0567 (3)0.0810 (14)
H23−0.11690.22230.06710.097*
C240.0248 (6)0.3247 (7)0.1140 (3)0.0831 (14)
H24−0.04730.32500.16350.100*
C250.1731 (5)0.3845 (5)0.0981 (2)0.0662 (11)
H250.20140.42270.13790.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0527 (5)0.0506 (4)0.0412 (4)−0.0108 (3)−0.0115 (3)−0.0058 (3)
O10.095 (2)0.0616 (16)0.0466 (16)−0.0208 (15)−0.0101 (15)−0.0057 (13)
O20.0734 (19)0.0650 (16)0.0448 (15)−0.0213 (14)−0.0214 (13)0.0030 (12)
O30.0584 (17)0.0690 (17)0.0536 (17)−0.0136 (13)−0.0069 (13)0.0071 (13)
O40.074 (2)0.079 (2)0.0613 (19)−0.0216 (16)−0.0135 (16)0.0065 (16)
O50.063 (2)0.083 (2)0.072 (2)−0.0164 (15)−0.0152 (16)−0.0020 (16)
O60.077 (2)0.0581 (16)0.0602 (18)−0.0128 (14)−0.0041 (15)−0.0130 (13)
O70.122 (3)0.0633 (18)0.0555 (19)−0.0167 (18)−0.0097 (19)−0.0052 (15)
O80.0549 (17)0.0801 (18)0.0533 (17)−0.0182 (14)−0.0148 (13)−0.0007 (13)
O90.070 (2)0.081 (2)0.066 (2)−0.0215 (16)−0.0178 (16)0.0090 (16)
O100.0594 (19)0.0753 (18)0.0654 (19)−0.0128 (14)−0.0149 (15)−0.0013 (14)
N10.0548 (19)0.0526 (17)0.0468 (18)−0.0099 (14)−0.0149 (14)−0.0030 (13)
C10.047 (2)0.058 (2)0.057 (2)−0.0130 (17)−0.0123 (17)−0.0068 (18)
C20.069 (3)0.064 (2)0.060 (3)−0.022 (2)−0.011 (2)−0.018 (2)
C30.061 (3)0.076 (3)0.051 (2)−0.014 (2)−0.0150 (19)−0.018 (2)
C40.057 (2)0.066 (2)0.047 (2)−0.0130 (19)−0.0110 (18)−0.0137 (18)
C50.054 (2)0.077 (3)0.055 (2)−0.008 (2)−0.0215 (19)−0.004 (2)
C60.067 (3)0.069 (2)0.050 (2)−0.014 (2)−0.021 (2)−0.0037 (19)
C70.062 (3)0.058 (2)0.048 (2)−0.0097 (18)−0.0177 (18)−0.0104 (17)
C80.057 (2)0.069 (2)0.059 (3)−0.0116 (19)−0.020 (2)−0.006 (2)
C90.060 (3)0.069 (2)0.052 (2)−0.012 (2)−0.0165 (19)0.0013 (19)
C100.062 (3)0.069 (2)0.047 (2)−0.014 (2)−0.0146 (19)−0.0124 (19)
C110.044 (2)0.069 (2)0.043 (2)−0.0153 (17)−0.0109 (16)−0.0061 (18)
C120.075 (3)0.086 (3)0.042 (2)−0.029 (2)−0.017 (2)−0.0023 (19)
C130.064 (3)0.084 (3)0.038 (2)−0.017 (2)−0.0119 (18)−0.0014 (18)
C140.057 (2)0.061 (2)0.040 (2)−0.0092 (18)−0.0070 (17)−0.0078 (16)
C150.055 (2)0.070 (2)0.042 (2)−0.0090 (19)−0.0146 (17)0.0022 (17)
C160.064 (3)0.061 (2)0.042 (2)−0.0092 (19)−0.0149 (18)0.0023 (17)
C170.060 (2)0.062 (2)0.038 (2)−0.0124 (18)−0.0089 (17)−0.0068 (16)
C180.054 (2)0.079 (3)0.061 (3)−0.006 (2)−0.018 (2)−0.001 (2)
C190.062 (3)0.067 (2)0.059 (3)−0.005 (2)−0.014 (2)0.0053 (19)
C200.052 (2)0.066 (2)0.047 (2)−0.0067 (19)−0.0114 (18)−0.0107 (18)
C210.061 (3)0.068 (2)0.060 (3)−0.017 (2)−0.013 (2)−0.013 (2)
C220.062 (3)0.088 (3)0.075 (3)−0.019 (2)−0.021 (2)−0.020 (2)
C230.058 (3)0.104 (4)0.087 (4)−0.032 (3)−0.023 (3)−0.003 (3)
C240.053 (3)0.123 (4)0.068 (3)−0.026 (3)−0.004 (2)−0.005 (3)
C250.060 (3)0.092 (3)0.046 (2)−0.017 (2)−0.010 (2)−0.009 (2)
Geometric parameters (Å, °) top
Co1—O22.062 (3)C6—C71.379 (5)
Co1—O62.125 (3)C6—H60.9300
Co1—N12.133 (3)C7—C81.401 (5)
Co1—O2i2.062 (3)C7—C101.477 (5)
Co1—O6i2.125 (3)C8—C91.369 (5)
Co1—N1i2.133 (3)C8—H80.9300
O1—C111.254 (5)C9—H90.9300
O2—C111.250 (4)C11—C121.512 (5)
O3—C141.355 (4)C12—C131.508 (5)
O3—C131.422 (5)C12—H110.9700
O4—C201.268 (5)C12—H120.9700
O4—H200.86 (5)C13—H130.9700
O5—C201.253 (5)C13—H140.9700
O6—C11.215 (4)C14—C191.382 (6)
O7—C11.276 (5)C14—C151.388 (5)
O7—H300.86 (3)C15—C161.384 (5)
O8—C41.365 (4)C15—H150.9300
O8—C31.432 (5)C16—C171.379 (5)
O9—C101.274 (5)C16—H160.9300
O9—H100.85 (5)C17—C181.398 (5)
O10—C101.266 (5)C17—C201.475 (5)
N1—C211.331 (5)C18—C191.363 (6)
N1—C251.340 (5)C18—H180.9300
C1—C21.507 (6)C19—H190.9300
C2—C31.502 (5)C21—C221.382 (6)
C2—H10.9700C21—H210.9300
C2—H20.9700C22—C231.352 (7)
C3—H30.9700C22—H220.9300
C3—H40.9700C23—C241.371 (7)
C4—C91.383 (6)C23—H230.9300
C4—C51.384 (5)C24—C251.367 (6)
C5—C61.379 (5)C24—H240.9300
C5—H50.9300C25—H250.9300
O2—Co1—O2i180.00 (16)C8—C9—H9119.7
O2—Co1—O682.86 (12)C4—C9—H9119.7
O2—Co1—O6i97.14 (12)O10—C10—O9123.0 (4)
O6—Co1—O6i180.00 (14)O10—C10—C7119.3 (4)
O2—Co1—N1i88.77 (11)O9—C10—C7117.7 (4)
O6—Co1—N1i91.89 (11)O2—C11—O1125.5 (4)
O2—Co1—N191.23 (11)O2—C11—C12116.9 (4)
O6—Co1—N188.11 (11)O1—C11—C12117.6 (3)
N1i—Co1—N1180.00 (17)C13—C12—C11114.3 (3)
O2i—Co1—O6i82.86 (12)C13—C12—H11108.7
O2i—Co1—N1i91.23 (11)C11—C12—H11108.7
O6i—Co1—N1i88.11 (11)C13—C12—H12108.7
O6i—Co1—N191.89 (11)C11—C12—H12108.7
O2i—Co1—N188.77 (11)H11—C12—H12107.6
O2i—Co1—O697.14 (12)O3—C13—C12106.5 (3)
C11—O2—Co1139.0 (2)O3—C13—H13110.4
C14—O3—C13118.3 (3)C12—C13—H13110.4
C20—O4—H20114 (4)O3—C13—H14110.4
C1—O6—Co1143.5 (3)C12—C13—H14110.4
C1—O7—H30123 (4)H13—C13—H14108.6
C4—O8—C3118.5 (3)O3—C14—C19115.7 (3)
C10—O9—H10111 (4)O3—C14—C15125.1 (4)
C21—N1—C25117.3 (3)C19—C14—C15119.2 (3)
C21—N1—Co1121.0 (3)C16—C15—C14119.6 (4)
C25—N1—Co1121.6 (3)C16—C15—H15120.2
O6—C1—O7123.6 (4)C14—C15—H15120.2
O6—C1—C2121.0 (4)C17—C16—C15121.3 (3)
O7—C1—C2115.4 (4)C17—C16—H16119.4
C3—C2—C1113.5 (3)C15—C16—H16119.4
C3—C2—H1108.9C16—C17—C18118.3 (3)
C1—C2—H1108.9C16—C17—C20121.5 (3)
C3—C2—H2108.9C18—C17—C20120.2 (4)
C1—C2—H2108.9C19—C18—C17120.6 (4)
H1—C2—H2107.7C19—C18—H18119.7
O8—C3—C2106.6 (3)C17—C18—H18119.7
O8—C3—H3110.4C18—C19—C14121.0 (4)
C2—C3—H3110.4C18—C19—H19119.5
O8—C3—H4110.4C14—C19—H19119.5
C2—C3—H4110.4O5—C20—O4122.9 (4)
H3—C3—H4108.6O5—C20—C17119.3 (4)
O8—C4—C9115.4 (3)O4—C20—C17117.8 (4)
O8—C4—C5124.9 (4)N1—C21—C22123.3 (4)
C9—C4—C5119.7 (4)N1—C21—H21118.4
C6—C5—C4119.5 (4)C22—C21—H21118.4
C6—C5—H5120.2C23—C22—C21118.5 (4)
C4—C5—H5120.2C23—C22—H22120.7
C7—C6—C5121.3 (4)C21—C22—H22120.7
C7—C6—H6119.4C22—C23—C24119.0 (4)
C5—C6—H6119.4C22—C23—H23120.5
C6—C7—C8118.7 (4)C24—C23—H23120.5
C6—C7—C10121.4 (4)C25—C24—C23119.8 (4)
C8—C7—C10119.8 (4)C25—C24—H24120.1
C9—C8—C7120.1 (4)C23—C24—H24120.1
C9—C8—H8120.0N1—C25—C24122.1 (4)
C7—C8—H8120.0N1—C25—H25119.0
C8—C9—C4120.7 (4)C24—C25—H25119.0
O6—Co1—O2—C11133.4 (4)C6—C7—C10—O10178.0 (4)
O6i—Co1—O2—C11−46.6 (4)C8—C7—C10—O10−2.9 (6)
N1i—Co1—O2—C11−134.6 (4)C6—C7—C10—O9−3.8 (6)
N1—Co1—O2—C1145.4 (4)C8—C7—C10—O9175.3 (4)
O2—Co1—O6—C1125.5 (5)Co1—O2—C11—O120.6 (6)
O2i—Co1—O6—C1−54.5 (5)Co1—O2—C11—C12−160.9 (3)
N1i—Co1—O6—C137.0 (5)O2—C11—C12—C13148.0 (4)
N1—Co1—O6—C1−143.0 (5)O1—C11—C12—C13−33.4 (6)
O2—Co1—N1—C21−141.4 (3)C14—O3—C13—C12177.7 (3)
O2i—Co1—N1—C2138.6 (3)C11—C12—C13—O3−67.6 (5)
O6—Co1—N1—C21135.8 (3)C13—O3—C14—C19178.8 (4)
O6i—Co1—N1—C21−44.2 (3)C13—O3—C14—C15−0.5 (6)
O2—Co1—N1—C2542.5 (3)O3—C14—C15—C16179.7 (4)
O2i—Co1—N1—C25−137.5 (3)C19—C14—C15—C160.5 (6)
O6—Co1—N1—C25−40.3 (3)C14—C15—C16—C17−0.6 (6)
O6i—Co1—N1—C25139.7 (3)C15—C16—C17—C180.4 (6)
Co1—O6—C1—O735.9 (7)C15—C16—C17—C20−178.9 (4)
Co1—O6—C1—C2−144.6 (4)C16—C17—C18—C19−0.1 (6)
O6—C1—C2—C3−28.8 (6)C20—C17—C18—C19179.3 (4)
O7—C1—C2—C3150.8 (4)C17—C18—C19—C140.0 (7)
C4—O8—C3—C2178.5 (3)O3—C14—C19—C18−179.5 (4)
C1—C2—C3—O8−74.8 (4)C15—C14—C19—C18−0.2 (6)
C3—O8—C4—C9172.7 (3)C16—C17—C20—O5−178.7 (4)
C3—O8—C4—C5−8.8 (6)C18—C17—C20—O52.0 (6)
O8—C4—C5—C6−178.7 (4)C16—C17—C20—O42.6 (6)
C9—C4—C5—C6−0.2 (6)C18—C17—C20—O4−176.8 (4)
C4—C5—C6—C70.5 (6)C25—N1—C21—C22−0.3 (6)
C5—C6—C7—C8−1.0 (6)Co1—N1—C21—C22−176.5 (3)
C5—C6—C7—C10178.1 (4)N1—C21—C22—C231.1 (7)
C6—C7—C8—C91.3 (6)C21—C22—C23—C24−0.5 (8)
C10—C7—C8—C9−177.8 (4)C22—C23—C24—C25−0.8 (8)
C7—C8—C9—C4−1.1 (6)C21—N1—C25—C24−1.1 (6)
O8—C4—C9—C8179.2 (4)Co1—N1—C25—C24175.1 (4)
C5—C4—C9—C80.6 (6)C23—C24—C25—N11.6 (8)
Symmetry codes: (i) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H30···O1i0.86 (3)1.58 (4)2.436 (4)178 (7)
O4—H20···O10ii0.86 (5)1.79 (5)2.637 (4)173 (6)
O9—H10···O5ii0.85 (5)1.79 (5)2.633 (4)172 (6)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x−1, −y, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Co1—O22.062 (3)Co1—N12.133 (3)
Co1—O62.125 (3)
O2—Co1—O682.86 (12)O6—Co1—N188.11 (11)
O2—Co1—N191.23 (11)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H30···O1i0.86 (3)1.58 (4)2.436 (4)178 (7)
O4—H20···O10ii0.86 (5)1.79 (5)2.637 (4)173 (6)
O9—H10···O5ii0.85 (5)1.79 (5)2.633 (4)172 (6)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x−1, −y, −z+1.
Acknowledgements top

The authors thank the Heilongjiang Province Natural Science Foundation (grant No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (grant No. 1054 G036) and Heilongjiang University for supporting this work.

references
References top

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