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Acta Cryst. (2008). E64, m1591-m1592    [ doi:10.1107/S1600536808038117 ]

Diaqua(2,9-dimethyl-1,10-phenanthroline-[kappa]2N,N')(4-hydroxybenzoato-[kappa]2O,O')cobalt(II) nitrate dihydrate

C. Zhai, F. Yan and P. Zhao

Abstract top

In the title compound, [Co(C7H5O3)(C14H12N2)(H2O)2]NO3·2H2O, the CoII ion is six-coordinated by two N atoms of a 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand, two carboxylate O atoms of one 4-hydroxybenzoate anion and two O atoms of two water molecules, in a distorted octahedral environment; the two water molecules occupy the apical positions. In the crystal structure, the ionic units and water molecules are linked through O-H...O hydrogen bonds, leading to the formation of a three-dimensional network. In addition, [pi]-[pi] interactions between a pyridine ring of the dmphen ligand and the benzene ring of the hydroxybenzoate anion [centroid-centroid separation = 3.6861 (3) Å] are observed.

Comment top

We have recently reported the syntheses and crystal structures of [Ni(dmphen)(3-OH-benzoate)(H2O)NO3] (Xuan & Zhao, 2007a), [Ni(dmphen)(benzoate)(H2O)NO3] (Xuan et al., 2007) and [Co(dmphen)(3-OH-benzoate)(H2O)NO3](Xuan & Zhao, 2007b) complexes. Now, we report here the crystal structure of the title compound.

Each CoII ion is six-coordinated by two N atoms from a dmphen ligand, and two O atoms from two water molecules and two O atoms from carboxylate group of one 4-hydroxy-benzoate anion (Fig.1). The CoO4N2 unit forms a distorted octahedral geometry, with two O atoms of two water molecules occupying the axial positions at 2.0685 (14) or 2.1187 (14) Å (Table 1). The equatorial plane is defined by the N atoms of dmphen and carboxy O atoms of the 3-hydroxybenzoate anion.

In the crystal structure, an extensive series of O—H···O hydrogen bonds, involving the coordinated and solvent water molecules, 4-hydroxybenzoate and nitrate anions, lead to a supramolecular network structure (Table 2 and Fig. 2). In addition, inversion related molecules are linked via π-π interactions involving the pyridine ring of the dmphen (N1/C1-C4/C12; centroid Cg1) ligand and the benzene ring of the hydroxybenzoate (C15—C20; centroid Cg2) anion (Fig.3); the Cg1—Cg2iii distance is 3.6861 (11) Å (symmetry code is given in Table 2). This combination of hydrogen bonds and stacking interactions build a three-dimensional network.

Related literature top

For related structures, see: Xuan et al. (2007); Xuan & Zhao (2007a,b).

Experimental top

To a solution of 2,9-dimethyl-1,10-phenanthroline (0.1095 g, 0.5 mmol), 4-hydroxy-benzoate (0.1382 g, 1 mmol) and sodium hydroxide (0.03740 g, 1 mmol) in ethanol-water (v:v 1:1, 15 ml) was added a solution of Ni(NO3)2.6H2O (0.1457 g, 0.5 mmol) in distilled water (10 ml). The resulting solution was stirred for 5 h at 323 K and then the precipitate obtained was filtered. Pink single crystals of the title compound were obtained by slow evaporation of the filtrate over 80 d.

Refinement top

C-bound H atoms were placed in calculated positions and were included in the refinement in the riding-model approximation, with C-H distances of 0.93 or 0.96 Å and Uiso(H) values of 1.2 or 1.5 times Ueq(C). The hydroxyl H atom was also placed in the calculated position (O-H = 0.82 Å) and refined with free torsion angles to fit the electron density. Water H atoms were located in a difference Fourier map and were allowed to ride on the parent atoms. For all O-bound H atoms the Uiso(H) values were set at 1.5 Ueq(O).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal structure of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.
Diaqua(2,9-dimethyl-1,10-phenanthroline-κ2N,N')(4- hydroxybenzoato-κ2O,O')cobalt(II) nitrate dihydrate top
Crystal data top
[Co(C7H5O3)(C14H12N2)(H2O)2]NO3·2H2OF(000) = 1116
Mr = 538.37Dx = 1.513 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6780 reflections
a = 9.8001 (8) Åθ = 2.3–27.4°
b = 22.2638 (19) ŵ = 0.79 mm−1
c = 10.8676 (9) ÅT = 291 K
β = 94.602 (1)°Block, pink
V = 2363.5 (3) Å30.35 × 0.25 × 0.14 mm
Z = 4
Data collection top
Buker SMART CCD area-detector
diffractometer		4385 independent reflections
Radiation source: fine-focus sealed tube3689 reflections with I > 2σ(I)
graphiteRint = 0.024
φ and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −11→11
Tmin = 0.771, Tmax = 0.899k = −26→26
17391 measured reflectionsl = −12→13
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)] = 0.029H-atom parameters constrained
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0425P)2 + 0.9518P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.002
4385 reflectionsΔρmax = 0.36 e Å−3
319 parametersΔρmin = −0.23 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0047 (4)
Crystal data top
[Co(C7H5O3)(C14H12N2)(H2O)2]NO3·2H2OV = 2363.5 (3) Å3
Mr = 538.37Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.8001 (8) ŵ = 0.79 mm−1
b = 22.2638 (19) ÅT = 291 K
c = 10.8676 (9) Å0.35 × 0.25 × 0.14 mm
β = 94.602 (1)°
Data collection top
Buker SMART CCD area-detector
diffractometer		4385 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		3689 reflections with I > 2σ(I)
Tmin = 0.771, Tmax = 0.899Rint = 0.024
17391 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.081Δρmax = 0.36 e Å−3
S = 1.01Δρmin = −0.23 e Å−3
4385 reflectionsAbsolute structure: ?
319 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Co10.24510 (2)0.564923 (11)0.97828 (2)0.02979 (10)
O10.17733 (13)0.49074 (6)1.08320 (12)0.0366 (3)
O20.33021 (13)0.47337 (6)0.95100 (12)0.0374 (3)
O30.2669 (2)0.21307 (7)1.18959 (16)0.0605 (5)
H30.29220.19021.13680.091*
O40.41725 (13)0.57880 (6)1.10585 (13)0.0393 (3)
H1W0.39850.56851.17490.059*
H2W0.49110.56351.08900.059*
O50.08164 (14)0.54783 (7)0.85063 (13)0.0463 (4)
H3W0.01200.54310.88660.070*
H4W0.07240.55130.77660.070*
O60.2587 (2)0.46630 (9)0.4839 (2)0.0894 (7)
O70.3605 (2)0.38408 (10)0.5460 (2)0.0809 (6)
O80.1450 (2)0.38603 (9)0.5079 (2)0.0793 (6)
N10.32511 (15)0.62761 (7)0.85585 (14)0.0318 (3)
N20.15796 (15)0.64623 (7)1.04080 (15)0.0335 (4)
N30.2548 (2)0.41299 (10)0.51267 (18)0.0539 (5)
C10.40177 (19)0.61783 (9)0.76179 (18)0.0365 (4)
C20.4510 (2)0.66576 (10)0.6932 (2)0.0453 (5)
H20.50280.65780.62700.054*
C30.4234 (2)0.72318 (10)0.7231 (2)0.0488 (5)
H3A0.45800.75470.67880.059*
C40.3424 (2)0.73521 (9)0.8210 (2)0.0411 (5)
C50.3063 (2)0.79459 (9)0.8560 (2)0.0508 (6)
H5A0.34280.82740.81700.061*
C60.2207 (3)0.80379 (9)0.9444 (2)0.0522 (6)
H6A0.19750.84280.96490.063*
C70.1645 (2)0.75432 (9)1.0074 (2)0.0425 (5)
C80.0722 (2)0.76153 (10)1.0991 (2)0.0523 (6)
H8A0.04270.79971.11950.063*
C90.0264 (2)0.71247 (10)1.1575 (2)0.0495 (6)
H9−0.03530.71721.21760.059*
C100.07125 (19)0.65450 (9)1.12827 (19)0.0393 (5)
C110.20282 (19)0.69525 (8)0.98025 (18)0.0343 (4)
C120.29325 (18)0.68556 (8)0.88414 (18)0.0334 (4)
C130.4357 (2)0.55479 (10)0.7305 (2)0.0475 (5)
H13A0.52020.54340.77520.071*
H13B0.44500.55170.64350.071*
H13C0.36380.52860.75270.071*
C140.0247 (2)0.60129 (10)1.1968 (2)0.0500 (6)
H14A−0.02720.57511.14060.075*
H14B−0.03170.61441.25990.075*
H14C0.10280.58021.23400.075*
C150.25751 (18)0.38985 (8)1.06962 (18)0.0315 (4)
C160.21346 (19)0.37361 (8)1.18382 (18)0.0350 (4)
H160.18130.40301.23500.042*
C170.2169 (2)0.31459 (9)1.22188 (19)0.0398 (5)
H170.18870.30441.29890.048*
C180.2626 (2)0.27028 (9)1.1450 (2)0.0401 (5)
C190.3045 (2)0.28577 (9)1.03029 (19)0.0408 (5)
H190.33340.25610.97810.049*
C200.3033 (2)0.34506 (9)0.99351 (19)0.0374 (4)
H200.33330.35520.91720.045*
C210.25521 (18)0.45407 (9)1.03250 (17)0.0326 (4)
O90.38611 (19)0.56246 (7)0.35357 (16)0.0590 (4)
H5W0.35200.53200.38240.089*
H6W0.46320.56960.38840.089*
O100.0934 (2)0.55782 (10)0.60222 (17)0.0801 (6)
H7W0.01950.56970.56950.120*
H8W0.10890.52280.58090.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02697 (15)0.02584 (15)0.03723 (16)0.00085 (9)0.00663 (10)0.00142 (10)
O10.0339 (7)0.0294 (7)0.0479 (8)0.0028 (5)0.0117 (6)0.0027 (6)
O20.0354 (7)0.0328 (7)0.0457 (8)−0.0002 (6)0.0131 (6)0.0061 (6)
O30.0890 (13)0.0308 (8)0.0644 (11)0.0015 (8)0.0237 (10)0.0087 (7)
O40.0313 (7)0.0439 (8)0.0428 (8)0.0022 (6)0.0042 (6)0.0025 (6)
O50.0323 (7)0.0644 (10)0.0423 (8)−0.0086 (7)0.0028 (6)0.0030 (7)
O60.123 (2)0.0482 (12)0.1012 (16)−0.0095 (11)0.0364 (15)0.0098 (10)
O70.0641 (12)0.0851 (14)0.0940 (16)0.0112 (11)0.0088 (11)−0.0044 (12)
O80.0701 (13)0.0730 (13)0.0944 (15)−0.0149 (11)0.0030 (11)0.0118 (11)
N10.0275 (8)0.0300 (8)0.0381 (9)0.0009 (6)0.0030 (6)0.0036 (7)
N20.0275 (8)0.0311 (8)0.0421 (9)0.0027 (6)0.0030 (7)−0.0035 (7)
N30.0643 (14)0.0494 (12)0.0491 (12)−0.0014 (10)0.0115 (10)−0.0038 (9)
C10.0293 (10)0.0426 (11)0.0375 (11)0.0018 (8)0.0022 (8)0.0050 (9)
C20.0391 (11)0.0553 (14)0.0422 (12)−0.0014 (10)0.0080 (9)0.0113 (10)
C30.0433 (12)0.0488 (13)0.0542 (14)−0.0077 (10)0.0030 (10)0.0193 (11)
C40.0393 (11)0.0342 (11)0.0484 (12)−0.0040 (8)−0.0049 (9)0.0097 (9)
C50.0586 (14)0.0299 (11)0.0622 (15)−0.0052 (10)−0.0047 (12)0.0104 (10)
C60.0642 (15)0.0247 (10)0.0656 (16)0.0058 (10)−0.0087 (12)0.0015 (10)
C70.0411 (12)0.0333 (11)0.0516 (13)0.0077 (9)−0.0055 (9)−0.0022 (9)
C80.0513 (13)0.0366 (12)0.0684 (16)0.0153 (10)0.0008 (11)−0.0092 (11)
C90.0425 (12)0.0484 (13)0.0589 (14)0.0131 (10)0.0111 (10)−0.0110 (11)
C100.0298 (10)0.0410 (11)0.0472 (12)0.0036 (8)0.0041 (8)−0.0066 (9)
C110.0306 (9)0.0285 (10)0.0426 (11)0.0013 (8)−0.0044 (8)0.0010 (8)
C120.0277 (9)0.0306 (10)0.0411 (11)0.0005 (7)−0.0028 (8)0.0034 (8)
C130.0509 (13)0.0468 (12)0.0471 (13)0.0047 (10)0.0180 (10)0.0009 (10)
C140.0475 (13)0.0481 (13)0.0576 (14)0.0002 (10)0.0235 (11)−0.0060 (11)
C150.0272 (9)0.0291 (9)0.0385 (10)−0.0024 (7)0.0041 (8)0.0015 (8)
C160.0323 (10)0.0337 (10)0.0396 (11)0.0005 (8)0.0071 (8)−0.0011 (8)
C170.0419 (11)0.0371 (11)0.0416 (11)−0.0036 (9)0.0109 (9)0.0064 (9)
C180.0424 (11)0.0292 (10)0.0489 (12)−0.0045 (8)0.0041 (9)0.0052 (9)
C190.0455 (11)0.0324 (10)0.0453 (12)−0.0011 (9)0.0082 (9)−0.0059 (9)
C200.0389 (11)0.0373 (11)0.0369 (11)−0.0017 (9)0.0090 (8)0.0007 (9)
C210.0283 (9)0.0324 (10)0.0373 (11)−0.0018 (8)0.0028 (8)0.0009 (8)
O90.0772 (12)0.0438 (9)0.0572 (10)0.0025 (8)0.0119 (9)0.0023 (7)
O100.0746 (13)0.1064 (17)0.0584 (12)0.0092 (11)0.0001 (10)−0.0031 (11)
Geometric parameters (Å, °) top
Co1—O52.0685 (14)C6—C71.430 (3)
Co1—O42.1187 (14)C6—H6A0.93
Co1—N12.1213 (15)C7—C111.406 (3)
Co1—N22.1357 (15)C7—C81.407 (3)
Co1—O12.1425 (13)C8—C91.358 (3)
Co1—O22.2311 (13)C8—H8A0.93
O1—C211.273 (2)C9—C101.408 (3)
O2—C211.270 (2)C9—H90.93
O3—C181.362 (2)C10—C141.490 (3)
O3—H30.82C11—C121.439 (3)
O4—H1W0.82C13—H13A0.96
O4—H2W0.83C13—H13B0.96
O5—H3W0.82C13—H13C0.96
O5—H4W0.81C14—H14A0.96
O6—N31.229 (3)C14—H14B0.96
O7—N31.249 (3)C14—H14C0.96
O8—N31.229 (3)C15—C201.392 (3)
N1—C11.334 (2)C15—C161.394 (3)
N1—C121.368 (2)C15—C211.485 (3)
N2—C101.338 (2)C16—C171.377 (3)
N2—C111.365 (2)C16—H160.93
C1—C21.409 (3)C17—C181.390 (3)
C1—C131.488 (3)C17—H170.93
C2—C31.352 (3)C18—C191.386 (3)
C2—H20.93C19—C201.379 (3)
C3—C41.403 (3)C19—H190.93
C3—H3A0.93C20—H200.93
C4—C121.407 (3)O9—H5W0.83
C4—C51.428 (3)O9—H6W0.83
C5—C61.341 (3)O10—H7W0.82
C5—H5A0.93O10—H8W0.83
O5—Co1—O4177.28 (6)C11—C7—C6120.0 (2)
O5—Co1—N190.33 (6)C8—C7—C6123.0 (2)
O4—Co1—N189.97 (6)C9—C8—C7119.7 (2)
O5—Co1—N293.52 (6)C9—C8—H8A120.2
O4—Co1—N289.19 (6)C7—C8—H8A120.2
N1—Co1—N279.59 (6)C8—C9—C10120.7 (2)
O5—Co1—O187.63 (6)C8—C9—H9119.7
O4—Co1—O191.65 (5)C10—C9—H9119.7
N1—Co1—O1170.71 (6)N2—C10—C9120.96 (19)
N2—Co1—O1109.58 (6)N2—C10—C14118.91 (17)
O5—Co1—O291.17 (6)C9—C10—C14120.12 (19)
O4—Co1—O286.19 (5)N2—C11—C7123.02 (19)
N1—Co1—O2110.90 (5)N2—C11—C12118.08 (16)
N2—Co1—O2168.50 (6)C7—C11—C12118.90 (18)
O1—Co1—O260.11 (5)N1—C12—C4122.56 (18)
C21—O1—Co192.40 (11)N1—C12—C11118.00 (16)
C21—O2—Co188.46 (11)C4—C12—C11119.42 (18)
C18—O3—H3109.5C1—C13—H13A109.5
Co1—O4—H1W109.5C1—C13—H13B109.5
Co1—O4—H2W117.1H13A—C13—H13B109.5
H1W—O4—H2W110.5C1—C13—H13C109.5
Co1—O5—H3W109.5H13A—C13—H13C109.5
Co1—O5—H4W132.1H13B—C13—H13C109.5
H3W—O5—H4W117.1C10—C14—H14A109.5
C1—N1—C12118.60 (16)C10—C14—H14B109.5
C1—N1—Co1129.23 (13)H14A—C14—H14B109.5
C12—N1—Co1112.14 (12)C10—C14—H14C109.5
C10—N2—C11118.69 (16)H14A—C14—H14C109.5
C10—N2—Co1129.48 (13)H14B—C14—H14C109.5
C11—N2—Co1111.83 (12)C20—C15—C16118.73 (17)
O6—N3—O8120.4 (2)C20—C15—C21121.77 (17)
O6—N3—O7122.0 (2)C16—C15—C21119.49 (17)
O8—N3—O7117.6 (2)C17—C16—C15120.86 (18)
N1—C1—C2121.30 (19)C17—C16—H16119.6
N1—C1—C13118.61 (17)C15—C16—H16119.6
C2—C1—C13120.09 (19)C16—C17—C18119.85 (18)
C3—C2—C1120.4 (2)C16—C17—H17120.1
C3—C2—H2119.8C18—C17—H17120.1
C1—C2—H2119.8O3—C18—C19123.33 (19)
C2—C3—C4119.94 (19)O3—C18—C17116.85 (18)
C2—C3—H3A120.0C19—C18—C17119.79 (18)
C4—C3—H3A120.0C20—C19—C18120.15 (19)
C3—C4—C12117.17 (19)C20—C19—H19119.9
C3—C4—C5123.1 (2)C18—C19—H19119.9
C12—C4—C5119.7 (2)C19—C20—C15120.59 (19)
C6—C5—C4121.0 (2)C19—C20—H20119.7
C6—C5—H5A119.5C15—C20—H20119.7
C4—C5—H5A119.5O2—C21—O1119.03 (18)
C5—C6—C7120.8 (2)O2—C21—C15121.20 (17)
C5—C6—H6A119.6O1—C21—C15119.77 (16)
C7—C6—H6A119.6H5W—O9—H6W111.3
C11—C7—C8116.9 (2)H7W—O10—H8W110.8
O5—Co1—O1—C2193.01 (11)C11—N2—C10—C90.2 (3)
O4—Co1—O1—C21−84.36 (11)Co1—N2—C10—C9179.14 (15)
N2—Co1—O1—C21−174.09 (11)C11—N2—C10—C14−178.51 (18)
O2—Co1—O1—C210.29 (10)Co1—N2—C10—C140.4 (3)
O5—Co1—O2—C21−86.88 (11)C8—C9—C10—N2−1.2 (3)
O4—Co1—O2—C2193.81 (11)C8—C9—C10—C14177.5 (2)
N1—Co1—O2—C21−177.68 (10)C10—N2—C11—C71.4 (3)
N2—Co1—O2—C2127.2 (3)Co1—N2—C11—C7−177.69 (15)
O1—Co1—O2—C21−0.29 (10)C10—N2—C11—C12−178.40 (17)
O5—Co1—N1—C1−83.02 (16)Co1—N2—C11—C122.5 (2)
O4—Co1—N1—C194.28 (16)C8—C7—C11—N2−2.0 (3)
N2—Co1—N1—C1−176.54 (17)C6—C7—C11—N2176.94 (19)
O2—Co1—N1—C18.36 (18)C8—C7—C11—C12177.86 (18)
O5—Co1—N1—C1298.92 (13)C6—C7—C11—C12−3.2 (3)
O4—Co1—N1—C12−83.79 (12)C1—N1—C12—C4−2.5 (3)
N2—Co1—N1—C125.40 (12)Co1—N1—C12—C4175.82 (14)
O2—Co1—N1—C12−169.70 (11)C1—N1—C12—C11175.81 (17)
O5—Co1—N2—C1087.09 (17)Co1—N1—C12—C11−5.9 (2)
O4—Co1—N2—C10−93.10 (17)C3—C4—C12—N12.1 (3)
N1—Co1—N2—C10176.78 (18)C5—C4—C12—N1−179.36 (18)
O1—Co1—N2—C10−1.64 (18)C3—C4—C12—C11−176.18 (18)
O2—Co1—N2—C10−26.8 (4)C5—C4—C12—C112.4 (3)
O5—Co1—N2—C11−93.90 (13)N2—C11—C12—N12.4 (3)
O4—Co1—N2—C1185.91 (13)C7—C11—C12—N1−177.50 (17)
N1—Co1—N2—C11−4.21 (12)N2—C11—C12—C4−179.31 (17)
O1—Co1—N2—C11177.37 (12)C7—C11—C12—C40.8 (3)
O2—Co1—N2—C11152.2 (2)C20—C15—C16—C171.0 (3)
C12—N1—C1—C20.8 (3)C21—C15—C16—C17−178.71 (17)
Co1—N1—C1—C2−177.17 (14)C15—C16—C17—C18−1.1 (3)
C12—N1—C1—C13−179.64 (17)C16—C17—C18—O3178.27 (19)
Co1—N1—C1—C132.4 (3)C16—C17—C18—C190.0 (3)
N1—C1—C2—C31.2 (3)O3—C18—C19—C20−176.9 (2)
C13—C1—C2—C3−178.3 (2)C17—C18—C19—C201.2 (3)
C1—C2—C3—C4−1.6 (3)C18—C19—C20—C15−1.4 (3)
C2—C3—C4—C120.0 (3)C16—C15—C20—C190.2 (3)
C2—C3—C4—C5−178.5 (2)C21—C15—C20—C19179.93 (18)
C3—C4—C5—C6175.1 (2)Co1—O2—C21—O10.49 (17)
C12—C4—C5—C6−3.3 (3)Co1—O2—C21—C15−179.24 (16)
C4—C5—C6—C70.9 (4)Co1—O1—C21—O2−0.51 (17)
C5—C6—C7—C112.4 (3)Co1—O1—C21—C15179.23 (15)
C5—C6—C7—C8−178.8 (2)C20—C15—C21—O2−21.5 (3)
C11—C7—C8—C90.9 (3)C16—C15—C21—O2158.19 (18)
C6—C7—C8—C9−178.0 (2)C20—C15—C21—O1158.77 (18)
C7—C8—C9—C100.6 (3)C16—C15—C21—O1−21.5 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O10—H8W···O60.832.262.960 (3)142
O9—H5W···O60.832.092.904 (3)169
O9—H6W···O7i0.832.092.888 (3)161
O10—H7W···O8ii0.832.012.829 (3)169
O5—H4W···O100.811.932.720 (2)167
O4—H2W···O2iii0.832.012.846 (2)180
O5—H3W···O1iv0.822.052.826 (2)157
O4—H1W···O9v0.821.962.758 (2)164
O3—H3···O8vi0.822.573.133 (3)127
O3—H3···O7vi0.822.072.861 (3)164
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y+1, −z+2; (v) x, y, z+1; (vi) x, −y+1/2, z+1/2.
Table 1
Selected geometric parameters (Å) top
Co1—O52.0685 (14)Co1—N22.1357 (15)
Co1—O42.1187 (14)Co1—O12.1425 (13)
Co1—N12.1213 (15)Co1—O22.2311 (13)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O10—H8W···O60.832.262.960 (3)142
O9—H5W···O60.832.092.904 (3)169
O9—H6W···O7i0.832.092.888 (3)161
O10—H7W···O8ii0.832.012.829 (3)169
O5—H4W···O100.811.932.720 (2)167
O4—H2W···O2iii0.832.012.846 (2)180
O5—H3W···O1iv0.822.052.826 (2)157
O4—H1W···O9v0.821.962.758 (2)164
O3—H3···O8vi0.822.573.133 (3)127
O3—H3···O7vi0.822.072.861 (3)164
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y+1, −z+2; (v) x, y, z+1; (vi) x, −y+1/2, z+1/2.
Acknowledgements top

Financial support from the Science Fund of Henan Province for Distinguished Young Scholars (grant No. 07410051005) is gratefully acknowledged.

references
References top

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

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

Westrip, S. P. (2008). publCIF. In preparation.

Xuan, X. & Zhao, P. (2007a). Acta Cryst. E63, m2856.

Xuan, X. & Zhao, P. (2007b). Acta Cryst. E63, m3009.

Xuan, X.-P., Zhao, P.-Z. & Tang, Q.-H. (2007). Acta Cryst. E63, m2405.