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Acta Cryst. (2007). E63, m1900-m1901    [ doi:10.1107/S1600536807027572 ]

Tetraaquabis[2-(3-benzoylphenyl)propanoato-[kappa]O]cobalt(II) monohydrate

Z.-Y. Zhang, P.-G. Chen, Z.-P. Deng, N. Yu and B.-Y. Liu

Abstract top

The title compound, [Co(C16H13O3)2(H2O)4]·H2O, is a transition metal complex of ketoprofen [2-(3-benzoylphenyl)propanoic acid], a well known nonsteroidal anti-inflammatory drug. The asymmetric unit consists of two half-complexes and one water molecule of crystallization. The CoII atoms are located on inversion centers and show an octahedral coordination geometry, defined by two carboxylate O atoms from two ketoprofenate ligands and four water molecules. The molecules are connected via O-H...O hydrogen bonds into a three-dimensional network.

Comment top

Crystal structure of only one metal complex of ketoprofen has been reported up till now. Ketoprofen forms with trimethyltin(IV)] a polymeric compound with the carboxylate group acting in a bidentate bridging mode (Tahir et al., 1997). Here we report crystal structure of the first transition metal complex of ketoprofen.

As illustrated in Fig. 1, the crystal structure of the title compound consists of two independent neutral mononuclear CoII complex molecules and one water of crystallization. The CoII atoms of the two molecules lie on inversion centers and display an octahedral geometry defined by two carboxylate O atoms of two ketoprofenato ligands and four water molecules. The Co1—Oketoprofenato and Co2—Oketoprofenato bond lengths are 2.134 (2) and 2.064 (2) Å, respectively. The Co—Owater bond lengths range from 2.051 (3) to 2.183 (2) Å. In the ketoprofenato ligands, two benzene rings are not coplanar, the dihedral angles are 70.1 (3) and 121.7 (3) °. A three-dimensional supramolecular network structure is formed through the extended hydrogen bonding interactions between water molecules and carboxylate O atoms (Table 2).

Related literature top

For the only crystal structure of the ketoprofen complex, (ketoprofenato)trimethyltin(IV), see: Tahir et al. (1997).

Experimental top

The title complex was prepared by the addition of cobalt diacetate trihydrate (2.31 g, 10 mmol) to a hot aqueous solution of 2-(3-benzoylphenyl)propanoic acid (3.65 g, 10 mmol); the pH was adjusted to 6 with 0.1M sodium hydroxide. The solution was allowed to evaporate at room temperature. Pink prismatic crystals separated from the filtered solution after several days. CH&N analysis. Calc. for C32H36CoO11: C 58.63, H 5.54%. Found: C 58.54, H 5.64%.

Refinement top

The H atoms were placed in calculated positions [C—H = 0.93 and 0.97 Å and Uiso(H) = 1.2Ueq (C) for aromatic H atoms and methine H atoms, respectively, C—H = 0.96 Å and Uiso(H) = 1.5Ueq (C) for methyl group H atoms] and were included in the refinement in the riding-model approximation. The H atoms of water molecules 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 Corporation, 1998); cell refinement: RAPID-AUTO; 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.

Figures top
[Figure 1] Fig. 1. Molecular structure of of the title compound with 30% probability ellipsoids for the non-H atoms.
Tetraaquabis[2-(3-benzoylphenyl)propanoato-κO]cobalt(II) monohydrate top
Crystal data top
[Co(C16H13O3)2(H2O)4]·H2OZ = 2
Mr = 655.54F000 = 686
Triclinic, P1Dx = 1.403 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.5966 (17) ÅCell parameters from 9690 reflections
b = 8.8939 (18) Åθ = 3.2–27.5º
c = 21.872 (4) ŵ = 0.61 mm−1
α = 92.08 (3)ºT = 295 (2) K
β = 99.69 (3)ºPrism, pink
γ = 108.92 (3)º0.36 × 0.28 × 0.19 mm
V = 1551.9 (6) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		7032 independent reflections
Radiation source: fine-focus sealed tube4192 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.049
Detector resolution: 10.000 pixels mm-1θmax = 27.5º
T = 295(2) Kθmin = 3.2º
ω scansh = −11→11
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −11→11
Tmin = 0.810, Tmax = 0.892l = −28→28
15351 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)] = 0.049H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.177  w = 1/[σ2(Fo2) + (0.0981P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
7032 reflectionsΔρmax = 0.75 e Å−3
432 parametersΔρmin = −0.62 e Å−3
15 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Co(C16H13O3)2(H2O)4]·H2Oγ = 108.92 (3)º
Mr = 655.54V = 1551.9 (6) Å3
Triclinic, P1Z = 2
a = 8.5966 (17) ÅMo Kα
b = 8.8939 (18) ŵ = 0.61 mm−1
c = 21.872 (4) ÅT = 295 (2) K
α = 92.08 (3)º0.36 × 0.28 × 0.19 mm
β = 99.69 (3)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		7032 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4192 reflections with I > 2σ(I)
Tmin = 0.810, Tmax = 0.892Rint = 0.049
15351 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04915 restraints
wR(F2) = 0.177H atoms treated by a mixture of
independent and constrained refinement
S = 1.05Δρmax = 0.75 e Å−3
7032 reflectionsΔρmin = −0.62 e Å−3
432 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.50000.00000.50000.02863 (19)
Co20.00000.50000.50000.02836 (19)
O10.7225 (4)−0.1111 (3)0.61833 (13)0.0555 (8)
O1W−0.1286 (5)0.6695 (4)0.63546 (13)0.0560 (8)
O20.7012 (3)0.1050 (3)0.57693 (10)0.0336 (5)
O2W0.3229 (3)0.0047 (3)0.55380 (13)0.0405 (6)
O3W0.4817 (3)−0.2333 (3)0.51952 (12)0.0401 (6)
O30.2059 (3)0.2647 (3)0.56416 (12)0.0432 (6)
O40.2168 (3)0.5170 (3)0.56140 (12)0.0417 (6)
O4W−0.1442 (4)0.4111 (3)0.56481 (13)0.0457 (7)
O5W0.0284 (3)0.7437 (3)0.53313 (12)0.0364 (6)
O50.9239 (5)0.6840 (4)0.76371 (14)0.0666 (10)
O60.3928 (5)0.6321 (4)0.91110 (14)0.0765 (11)
C10.9958 (9)0.6929 (7)0.9782 (2)0.0874 (19)
H11.06150.67351.01330.105*
C20.9025 (9)0.7898 (7)0.9845 (3)0.090 (2)
H20.90210.83281.02380.108*
C30.8116 (9)0.8226 (7)0.9336 (3)0.0860 (19)
H30.74890.88860.93810.103*
C40.8102 (7)0.7592 (5)0.8744 (2)0.0638 (13)
H40.74980.78530.83950.077*
C50.8998 (6)0.6566 (5)0.86799 (19)0.0469 (10)
C60.9929 (7)0.6236 (6)0.9199 (2)0.0662 (14)
H61.05360.55530.91600.079*
C70.8989 (5)0.5920 (5)0.80391 (18)0.0436 (9)
C80.8629 (5)0.4175 (5)0.78967 (17)0.0412 (9)
C90.9120 (5)0.3631 (4)0.73750 (15)0.0351 (8)
H90.97730.43650.71490.042*
C100.8645 (5)0.2020 (4)0.71943 (16)0.0359 (8)
C110.7664 (6)0.0951 (5)0.75340 (19)0.0531 (11)
H110.7331−0.01390.74150.064*
C120.7169 (7)0.1480 (5)0.8050 (2)0.0655 (14)
H120.64950.07470.82710.079*
C130.7674 (6)0.3083 (5)0.82348 (19)0.0523 (11)
H130.73720.34340.85880.063*
C140.9233 (5)0.1427 (4)0.66370 (15)0.0343 (8)
H140.98030.23610.64350.041*
C151.0479 (5)0.0574 (5)0.68472 (18)0.0449 (10)
H15A1.14530.13050.71150.067*
H15B1.07990.01870.64890.067*
H15C0.9969−0.03090.70700.067*
C160.7703 (5)0.0361 (4)0.61625 (16)0.0338 (8)
C170.2352 (7)0.0842 (6)0.8625 (2)0.0667 (14)
H170.1514−0.00460.84020.080*
C180.3483 (8)0.0650 (7)0.9110 (2)0.0745 (16)
H180.3432−0.03700.92090.089*
C190.4708 (7)0.1977 (6)0.9453 (2)0.0659 (14)
H190.54720.18440.97840.079*
C200.4789 (6)0.3479 (6)0.93060 (18)0.0573 (12)
H200.55940.43650.95430.069*
C210.3676 (5)0.3689 (5)0.88030 (17)0.0469 (10)
C220.2456 (6)0.2351 (5)0.84673 (19)0.0543 (11)
H220.16990.24750.81320.065*
C230.3743 (6)0.5346 (5)0.86745 (19)0.0522 (11)
C240.3617 (5)0.5821 (4)0.80224 (18)0.0420 (9)
C250.3313 (6)0.7258 (5)0.7927 (2)0.0541 (11)
H250.31370.78420.82540.065*
C260.3277 (6)0.7794 (5)0.7345 (2)0.0608 (13)
H260.30700.87450.72820.073*
C270.3540 (6)0.6956 (5)0.6852 (2)0.0524 (11)
H270.35140.73490.64640.063*
C280.3846 (5)0.5518 (5)0.69338 (17)0.0412 (9)
C290.3868 (5)0.4972 (5)0.75199 (17)0.0414 (9)
H290.40560.40110.75800.050*
C300.4215 (5)0.4663 (5)0.63817 (17)0.0444 (10)
H300.50690.54870.62190.053*
C310.4963 (6)0.3409 (6)0.6545 (2)0.0581 (12)
H31A0.59430.38500.68660.087*
H31B0.52680.30250.61830.087*
H31C0.41630.25420.66930.087*
C320.2669 (5)0.4081 (4)0.58425 (16)0.0351 (8)
H3W10.554 (4)−0.213 (4)0.5531 (11)0.053*
H1W1−0.185 (5)0.732 (4)0.6325 (16)0.053*
H2W10.296 (4)0.088 (2)0.551 (2)0.053*
H2W20.234 (3)−0.076 (3)0.5474 (19)0.053*
H3W20.395 (3)−0.311 (3)0.5224 (16)0.053*
H4W1−0.202 (5)0.3180 (18)0.5707 (18)0.053*
H5W1−0.049 (4)0.750 (5)0.5046 (12)0.053*
H1W2−0.082 (5)0.672 (5)0.6731 (8)0.053*
H4W2−0.166 (5)0.481 (3)0.5861 (17)0.053*
H5W2−0.009 (4)0.721 (5)0.5663 (10)0.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0258 (4)0.0237 (3)0.0323 (3)0.0044 (3)0.0025 (3)0.0026 (3)
Co20.0252 (4)0.0243 (3)0.0320 (3)0.0048 (3)0.0028 (3)0.0030 (3)
O10.0560 (19)0.0321 (14)0.0627 (18)0.0085 (13)−0.0203 (15)0.0110 (13)
O1W0.084 (3)0.0487 (17)0.0439 (16)0.0372 (17)0.0068 (15)−0.0004 (14)
O20.0301 (14)0.0295 (12)0.0366 (12)0.0082 (10)−0.0028 (10)0.0041 (10)
O2W0.0346 (15)0.0307 (13)0.0545 (15)0.0071 (11)0.0122 (12)−0.0009 (12)
O3W0.0333 (15)0.0288 (12)0.0478 (15)0.0002 (11)−0.0007 (11)0.0091 (11)
O30.0428 (16)0.0380 (14)0.0473 (15)0.0152 (12)0.0007 (12)0.0059 (12)
O40.0341 (15)0.0326 (13)0.0513 (15)0.0106 (11)−0.0101 (12)0.0044 (11)
O4W0.0594 (19)0.0279 (13)0.0486 (16)0.0049 (13)0.0264 (13)0.0047 (12)
O5W0.0349 (15)0.0288 (12)0.0419 (14)0.0063 (11)0.0069 (11)0.0012 (11)
O50.113 (3)0.0494 (17)0.0480 (17)0.0370 (19)0.0229 (18)0.0081 (15)
O60.116 (3)0.072 (2)0.0417 (17)0.037 (2)0.0081 (18)−0.0142 (16)
C10.122 (6)0.082 (4)0.044 (3)0.019 (4)0.004 (3)0.002 (3)
C20.136 (6)0.061 (3)0.059 (3)0.005 (4)0.040 (4)−0.017 (3)
C30.104 (5)0.070 (3)0.089 (4)0.024 (3)0.047 (4)−0.016 (3)
C40.073 (4)0.054 (3)0.067 (3)0.024 (3)0.017 (2)−0.006 (2)
C50.055 (3)0.036 (2)0.047 (2)0.0096 (19)0.0177 (19)−0.0023 (18)
C60.085 (4)0.069 (3)0.047 (3)0.028 (3)0.011 (2)0.004 (2)
C70.050 (3)0.043 (2)0.039 (2)0.0201 (19)0.0069 (17)−0.0001 (18)
C80.039 (2)0.043 (2)0.0383 (19)0.0115 (18)0.0054 (16)0.0009 (17)
C90.037 (2)0.0393 (19)0.0296 (17)0.0146 (16)0.0031 (14)0.0029 (15)
C100.034 (2)0.0374 (19)0.0323 (18)0.0091 (16)0.0015 (15)0.0004 (15)
C110.061 (3)0.039 (2)0.052 (2)0.004 (2)0.016 (2)−0.0024 (19)
C120.082 (4)0.049 (3)0.057 (3)0.002 (2)0.033 (3)0.003 (2)
C130.065 (3)0.051 (2)0.043 (2)0.017 (2)0.021 (2)0.0014 (19)
C140.033 (2)0.0337 (18)0.0319 (17)0.0084 (15)0.0009 (14)0.0011 (15)
C150.038 (2)0.046 (2)0.047 (2)0.0157 (18)−0.0043 (17)−0.0044 (18)
C160.034 (2)0.0297 (17)0.0347 (18)0.0071 (15)0.0052 (15)0.0020 (15)
C170.087 (4)0.057 (3)0.050 (3)0.016 (3)0.012 (2)0.000 (2)
C180.122 (5)0.067 (3)0.048 (3)0.046 (3)0.027 (3)0.013 (2)
C190.085 (4)0.083 (4)0.039 (2)0.042 (3)0.006 (2)0.005 (2)
C200.062 (3)0.073 (3)0.034 (2)0.023 (3)0.0009 (19)−0.005 (2)
C210.050 (3)0.054 (2)0.0337 (19)0.017 (2)0.0049 (17)−0.0023 (18)
C220.059 (3)0.059 (3)0.039 (2)0.018 (2)−0.0022 (19)−0.002 (2)
C230.052 (3)0.057 (3)0.041 (2)0.015 (2)0.0042 (18)−0.010 (2)
C240.040 (2)0.041 (2)0.041 (2)0.0141 (18)0.0005 (16)−0.0052 (17)
C250.061 (3)0.054 (3)0.050 (2)0.027 (2)0.003 (2)−0.008 (2)
C260.077 (4)0.049 (2)0.060 (3)0.033 (2)0.002 (2)−0.008 (2)
C270.063 (3)0.049 (2)0.046 (2)0.025 (2)0.002 (2)0.0027 (19)
C280.043 (2)0.045 (2)0.0362 (19)0.0198 (18)−0.0018 (16)−0.0020 (17)
C290.041 (2)0.042 (2)0.041 (2)0.0170 (18)0.0008 (16)−0.0052 (17)
C300.048 (3)0.050 (2)0.0351 (19)0.021 (2)0.0001 (17)0.0011 (17)
C310.048 (3)0.075 (3)0.054 (3)0.030 (2)−0.002 (2)−0.006 (2)
C320.031 (2)0.041 (2)0.0337 (18)0.0121 (16)0.0086 (15)0.0025 (16)
Geometric parameters (Å, °) top
Co1—O2W2.084 (3)C9—H90.9300
Co1—O3W2.095 (2)C10—C111.382 (6)
Co1—O22.134 (2)C10—C141.534 (5)
Co2—O4W2.051 (3)C11—C121.389 (6)
Co2—O42.064 (2)C11—H110.9300
Co2—O5W2.183 (2)C12—C131.372 (6)
Co1—O2Wi2.084 (3)C12—H120.9300
Co1—O3Wi2.095 (2)C13—H130.9300
Co1—O2i2.134 (2)C14—C151.524 (5)
Co2—O4Wii2.051 (3)C14—C161.539 (5)
Co2—O4ii2.064 (2)C14—H140.9800
Co2—O5Wii2.183 (2)C15—H15A0.9600
O1—C161.244 (4)C15—H15B0.9600
O1W—H1W10.85 (4)C15—H15C0.9600
O1W—H1W20.848 (10)C17—C181.369 (7)
O2—C161.253 (4)C17—C221.376 (7)
O2W—H2W10.850 (10)C17—H170.9300
O2W—H2W20.85 (3)C18—C191.389 (8)
O3W—H3W10.85 (3)C18—H180.9300
O3W—H3W20.85 (3)C19—C201.368 (7)
O3—C321.242 (4)C19—H190.9300
O4—C321.268 (4)C20—C211.392 (6)
O4W—H4W10.845 (10)C20—H200.9300
O4W—H4W20.85 (4)C21—C221.387 (6)
O5W—H5W10.85 (3)C21—C231.495 (6)
O5W—H5W20.85 (3)C22—H220.9300
O5—C71.221 (5)C23—C241.499 (6)
O6—C231.220 (5)C24—C291.396 (5)
C1—C21.370 (9)C24—C251.401 (6)
C1—C61.390 (7)C25—C261.375 (6)
C1—H10.9300C25—H250.9300
C2—C31.347 (9)C26—C271.379 (6)
C2—H20.9300C26—H260.9300
C3—C41.389 (7)C27—C281.399 (6)
C3—H30.9300C27—H270.9300
C4—C51.389 (6)C28—C291.386 (5)
C4—H40.9300C28—C301.535 (5)
C5—C61.373 (6)C29—H290.9300
C5—C71.494 (5)C30—C311.484 (6)
C6—H60.9300C30—C321.551 (5)
C7—C81.490 (5)C30—H300.9800
C8—C131.380 (6)C31—H31A0.9600
C8—C91.403 (5)C31—H31B0.9600
C9—C101.379 (5)C31—H31C0.9600
O2W—Co1—O3W91.81 (11)C12—C11—H11119.5
O2W—Co1—O3Wi88.19 (11)C13—C12—C11120.0 (4)
O2W—Co1—O2i88.33 (10)C13—C12—H12120.0
O3W—Co1—O2i86.82 (10)C11—C12—H12120.0
O2W—Co1—O291.67 (10)C12—C13—C8120.1 (4)
O3W—Co1—O293.18 (10)C12—C13—H13120.0
O4W—Co2—O4ii88.35 (12)C8—C13—H13120.0
O4W—Co2—O5Wii89.34 (10)C15—C14—C10111.2 (3)
O4—Co2—O5Wii90.54 (10)C15—C14—C16112.2 (3)
O4W—Co2—O5W90.66 (10)C10—C14—C16109.5 (3)
O4—Co2—O5W89.46 (10)C15—C14—H14108.0
O2Wi—Co1—O2W180.000 (1)C10—C14—H14108.0
O2Wi—Co1—O3W88.19 (11)C16—C14—H14108.0
O2Wi—Co1—O3Wi91.81 (11)C14—C15—H15A109.5
O3W—Co1—O3Wi180.00 (3)C14—C15—H15B109.5
O2Wi—Co1—O2i91.67 (10)H15A—C15—H15B109.5
O3Wi—Co1—O2i93.18 (10)C14—C15—H15C109.5
O2Wi—Co1—O288.33 (10)H15A—C15—H15C109.5
O3Wi—Co1—O286.82 (10)H15B—C15—H15C109.5
O2i—Co1—O2180.0O1—C16—O2123.7 (3)
O4W—Co2—O4Wii180.000 (1)O1—C16—C14119.4 (3)
O4Wii—Co2—O4ii91.65 (12)O2—C16—C14116.9 (3)
O4W—Co2—O491.65 (12)C18—C17—C22119.9 (5)
O4Wii—Co2—O488.35 (12)C18—C17—H17120.1
O4ii—Co2—O4180.000 (1)C22—C17—H17120.1
O4Wii—Co2—O5Wii90.66 (10)C17—C18—C19120.1 (5)
O4ii—Co2—O5Wii89.46 (10)C17—C18—H18119.9
O4Wii—Co2—O5W89.34 (10)C19—C18—H18119.9
O4ii—Co2—O5W90.54 (10)C20—C19—C18120.0 (5)
O5Wii—Co2—O5W180.00 (13)C20—C19—H19120.0
H1W1—O1W—H1W2110 (2)C18—C19—H19120.0
C16—O2—Co1128.2 (2)C19—C20—C21120.4 (4)
Co1—O2W—H2W1113 (3)C19—C20—H20119.8
Co1—O2W—H2W2116 (3)C21—C20—H20119.8
H2W1—O2W—H2W2108 (2)C22—C21—C20118.8 (4)
Co1—O3W—H3W199 (3)C22—C21—C23122.0 (4)
Co1—O3W—H3W2129 (3)C20—C21—C23119.0 (4)
H3W1—O3W—H3W2111 (2)C17—C22—C21120.7 (4)
C32—O4—Co2130.0 (2)C17—C22—H22119.6
Co2—O4W—H4W1133 (2)C21—C22—H22119.6
Co2—O4W—H4W2115 (2)O6—C23—C21118.9 (4)
H4W1—O4W—H4W2111 (2)O6—C23—C24120.1 (4)
Co2—O5W—H5W194 (3)C21—C23—C24120.9 (3)
Co2—O5W—H5W296 (3)C29—C24—C25118.8 (4)
H5W1—O5W—H5W2110 (2)C29—C24—C23124.3 (4)
C2—C1—C6120.6 (6)C25—C24—C23116.8 (4)
C2—C1—H1119.7C26—C25—C24119.2 (4)
C6—C1—H1119.7C26—C25—H25120.4
C3—C2—C1119.9 (5)C24—C25—H25120.4
C3—C2—H2120.0C25—C26—C27121.7 (4)
C1—C2—H2120.0C25—C26—H26119.1
C2—C3—C4121.0 (6)C27—C26—H26119.1
C2—C3—H3119.5C26—C27—C28120.3 (4)
C4—C3—H3119.5C26—C27—H27119.9
C5—C4—C3119.3 (5)C28—C27—H27119.9
C5—C4—H4120.3C29—C28—C27118.0 (4)
C3—C4—H4120.3C29—C28—C30123.3 (3)
C6—C5—C4119.7 (4)C27—C28—C30118.7 (4)
C6—C5—C7121.8 (4)C28—C29—C24122.0 (4)
C4—C5—C7118.5 (4)C28—C29—H29119.0
C5—C6—C1119.5 (5)C24—C29—H29119.0
C5—C6—H6120.3C31—C30—C28115.1 (3)
C1—C6—H6120.3C31—C30—C32113.2 (3)
O5—C7—C8121.4 (3)C28—C30—C32111.2 (3)
O5—C7—C5118.6 (3)C31—C30—H30105.5
C8—C7—C5120.0 (4)C28—C30—H30105.5
C13—C8—C9119.5 (4)C32—C30—H30105.5
C13—C8—C7120.6 (4)C30—C31—H31A109.5
C9—C8—C7119.6 (4)C30—C31—H31B109.5
C10—C9—C8120.7 (4)H31A—C31—H31B109.5
C10—C9—H9119.7C30—C31—H31C109.5
C8—C9—H9119.7H31A—C31—H31C109.5
C9—C10—C11118.7 (3)H31B—C31—H31C109.5
C9—C10—C14120.5 (3)O3—C32—O4124.3 (3)
C11—C10—C14120.7 (3)O3—C32—C30120.3 (3)
C10—C11—C12120.9 (4)O4—C32—C30115.3 (3)
C10—C11—H11119.5
O2Wi—Co1—O2—C16−88.5 (3)C15—C14—C16—O129.8 (5)
O2W—Co1—O2—C1691.5 (3)C10—C14—C16—O1−94.1 (4)
O3W—Co1—O2—C16−0.4 (3)C15—C14—C16—O2−149.8 (3)
O3Wi—Co1—O2—C16179.6 (3)C10—C14—C16—O286.3 (4)
O4W—Co2—O4—C3267.1 (3)C22—C17—C18—C191.7 (8)
O4Wii—Co2—O4—C32−112.9 (3)C17—C18—C19—C20−0.3 (8)
O5Wii—Co2—O4—C32−22.2 (3)C18—C19—C20—C21−1.6 (8)
O5W—Co2—O4—C32157.8 (3)C19—C20—C21—C221.9 (7)
C6—C1—C2—C3−2.2 (10)C19—C20—C21—C23176.9 (4)
C1—C2—C3—C40.2 (10)C18—C17—C22—C21−1.3 (8)
C2—C3—C4—C52.0 (9)C20—C21—C22—C17−0.4 (7)
C3—C4—C5—C6−2.2 (8)C23—C21—C22—C17−175.3 (5)
C3—C4—C5—C7−179.0 (5)C22—C21—C23—O6133.1 (5)
C4—C5—C6—C10.2 (8)C20—C21—C23—O6−41.8 (7)
C7—C5—C6—C1176.9 (5)C22—C21—C23—C24−48.1 (6)
C2—C1—C6—C52.0 (9)C20—C21—C23—C24137.1 (4)
C6—C5—C7—O5−129.8 (5)O6—C23—C24—C29161.5 (4)
C4—C5—C7—O546.9 (6)C21—C23—C24—C29−17.4 (7)
C6—C5—C7—C852.0 (6)O6—C23—C24—C25−15.1 (7)
C4—C5—C7—C8−131.3 (4)C21—C23—C24—C25166.1 (4)
O5—C7—C8—C13−151.7 (4)C29—C24—C25—C26−0.3 (7)
C5—C7—C8—C1326.4 (6)C23—C24—C25—C26176.5 (4)
O5—C7—C8—C921.7 (6)C24—C25—C26—C27−0.3 (8)
C5—C7—C8—C9−160.1 (4)C25—C26—C27—C280.3 (8)
C13—C8—C9—C100.6 (6)C26—C27—C28—C290.2 (7)
C7—C8—C9—C10−172.9 (3)C26—C27—C28—C30−177.1 (4)
C8—C9—C10—C110.5 (6)C27—C28—C29—C24−0.8 (6)
C8—C9—C10—C14−177.9 (3)C30—C28—C29—C24176.4 (4)
C9—C10—C11—C12−0.3 (7)C25—C24—C29—C280.8 (6)
C14—C10—C11—C12178.1 (4)C23—C24—C29—C28−175.7 (4)
C10—C11—C12—C13−0.9 (8)C29—C28—C30—C31−12.9 (6)
C11—C12—C13—C82.1 (8)C27—C28—C30—C31164.3 (4)
C9—C8—C13—C12−1.9 (7)C29—C28—C30—C32117.4 (4)
C7—C8—C13—C12171.6 (4)C27—C28—C30—C32−65.4 (5)
C9—C10—C14—C15110.7 (4)Co2—O4—C32—O314.4 (6)
C11—C10—C14—C15−67.7 (5)Co2—O4—C32—C30−169.4 (2)
C9—C10—C14—C16−124.8 (4)C31—C30—C32—O38.2 (5)
C11—C10—C14—C1656.8 (5)C28—C30—C32—O3−123.1 (4)
Co1—O2—C16—O1−4.6 (6)C31—C30—C32—O4−168.2 (4)
Co1—O2—C16—C14174.9 (2)C28—C30—C32—O460.5 (5)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3W—H3W1···O10.85 (3)1.82 (3)2.646 (4)164 (4)
O1W—H1W1···O1iii0.85 (4)1.83 (4)2.665 (4)170 (4)
O2W—H2W1···O30.850 (10)1.990 (15)2.822 (4)166 (4)
O2W—H2W2···O5Wiv0.85 (3)1.93 (3)2.781 (4)179 (4)
O3W—H3W2···O4iv0.85 (3)2.107 (16)2.920 (4)161 (3)
O4W—H4W1···O2v0.85 (3)1.826 (12)2.660 (4)169 (4)
O5W—H5W1···O3ii0.85 (3)1.81 (3)2.653 (4)170 (4)
O1W—H1W2···O5v0.848 (10)1.97 (2)2.757 (4)154 (4)
O4W—H4W2···O1W0.85 (4)1.867 (16)2.675 (4)159 (4)
O5W—H5W2···O1W0.85 (3)1.96 (3)2.795 (4)171 (4)
Symmetry codes: (iii) x−1, y+1, z; (iv) x, y−1, z; (v) x−1, y, z; (ii) −x, −y+1, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Co1—O2W2.084 (3)Co2—O4W2.051 (3)
Co1—O3W2.095 (2)Co2—O42.064 (2)
Co1—O22.134 (2)Co2—O5W2.183 (2)
O2W—Co1—O3W91.81 (11)O4W—Co2—O4ii88.35 (12)
O2W—Co1—O3Wi88.19 (11)O4W—Co2—O5Wii89.34 (10)
O2W—Co1—O2i88.33 (10)O4—Co2—O5Wii90.54 (10)
O3W—Co1—O2i86.82 (10)O4W—Co2—O5W90.66 (10)
O2W—Co1—O291.67 (10)O4—Co2—O5W89.46 (10)
O3W—Co1—O293.18 (10)O4W—Co2—O491.65 (12)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3W—H3W1···O10.85 (3)1.82 (3)2.646 (4)164 (4)
O1W—H1W1···O1iii0.85 (4)1.83 (4)2.665 (4)170 (4)
O2W—H2W1···O30.850 (10)1.990 (15)2.822 (4)166 (4)
O2W—H2W2···O5Wiv0.85 (3)1.93 (3)2.781 (4)179 (4)
O3W—H3W2···O4iv0.85 (3)2.107 (16)2.920 (4)161 (3)
O4W—H4W1···O2v0.85 (3)1.826 (12)2.660 (4)169 (4)
O5W—H5W1···O3ii0.85 (3)1.81 (3)2.653 (4)170 (4)
O1W—H1W2···O5v0.848 (10)1.97 (2)2.757 (4)154 (4)
O4W—H4W2···O1W0.85 (4)1.867 (16)2.675 (4)159 (4)
O5W—H5W2···O1W0.85 (3)1.96 (3)2.795 (4)171 (4)
Symmetry codes: (iii) x−1, y+1, z; (iv) x, y−1, z; (v) x−1, y, z; (ii) −x, −y+1, −z+1.
Acknowledgements top

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

references
References top

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