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Acta Cryst. (2007). E63, m2883    [ doi:10.1107/S1600536807052762 ]

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

Z.-Y. Zhang, N. Yu, X.-X. Guo, J. Pu and J.-P. Sun

Abstract top

The title complex, [Ni(C16H13O3)2(H2O)4]·H2O, is a transition metal complex of ketoprofen [2-(3-benzoylphenyl)propanoic acid], a well known non-steroidal anti-inflammatory drug. The asymmetric unit consists of half each of two complex molecules and one solvent water molecule. Both NiII atoms are located on crystallographic centres of inversion, each exhibiting an octahedral coordination geometry involving two carboxylate O atoms of different ketoprofenate ligands and four water molecules. A three-dimensional hydrogen-bonding framework is formed by O-H...O hydrogen-bonding interactions.

Comment top

2-(3-benzoylphenyl)propanoic acid is known as a nonsteroidal anti-inflamatory drug, but there is little information on the structure of its metal complexes (Tahir et al., 1997). The preceeding report (Zhang et al., 2007) details the synthesis and crystal structure of tetraaquabis[2-(3-benzoylphenyl)propanoato-κO] cobalt(II) monohydrate. Replacing cobalt by nickel in a similar reaction leads to the formation of the title complex, (I), (Fig. 1). Similar structural descriptions of the CoII apply to the isomorphous complex.

As illustrated in Fig. 1, the crystal structure of the title compound consists of two crystallographically independent neutral mononuclear NiII complex molecules and one water of crystallization. The NiII atoms of the two molecules are situated at crystallographic centers of inversion and display an octahedral geometry defined by two carboxylate O atoms of two ketoprofenato ligands and four water molecules. A three-dimensional supramolecular network structure is formed through the extended hydrogen bonding interactions between water molecules and carboxylate O atoms (Table 1).

Related literature top

For the crystal structures of the ketoprofen complexes (ketoprofenato)trimethyltin(IV) and tetraaquabis[2-(3-benzoylphenyl)propanoato-κO]nickel(II) monohydrate, see: Tahir et al. (1997); Zhang et al. (2007).

Experimental top

The title complex was prepared by the addition of nickel diacetate tetrahydrate (2.49 g, 10 mmol) to a hot aqueous solution of racemic 2-(3-benzoylphenyl)propanoic acid (2.54 g, 10 mmol); the pH was adjusted to 6 with 0.1M sodium hydroxide. The solution was allowed to evaporate at room temperature. Green prismatic crystals separated from the filtered solution after several days. Elemental analysis: calcd. for C32H36NiO11: C 58.63, H 5.54%; found: C 58.52, H 5.69%.

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, 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 (I) with 30% probability ellipsoids for the non-H atoms.
Tetraaquabis[2-(3-benzoylphenyl)propanoato-κO]nickel(II) monohydrate top
Crystal data top
[Ni(C16H13O3)2(H2O)4]·H2OZ = 2
Mr = 655.32F000 = 688
Triclinic, P1Dx = 1.415 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.559 (2) ÅCell parameters from 7166 reflections
b = 8.851 (2) Åθ = 3.2–27.5º
c = 21.875 (4) ŵ = 0.69 mm−1
α = 92.05 (3)ºT = 295 (2) K
β = 99.78 (3)ºSheet, pale green
γ = 108.90 (3)º0.34 × 0.25 × 0.19 mm
V = 1537.7 (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 = 27.6º
T = 295(2) Kθmin = 3.2º
ω scansh = −11→11
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −11→11
Tmin = 0.799, Tmax = 0.880l = −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)] = 0.053H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.174  w = 1/[σ2(Fo2) + (0.0853P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
7032 reflectionsΔρmax = 0.78 e Å−3
432 parametersΔρmin = −0.74 e Å−3
15 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ni(C16H13O3)2(H2O)4]·H2Oγ = 108.90 (3)º
Mr = 655.32V = 1537.7 (6) Å3
Triclinic, P1Z = 2
a = 8.559 (2) ÅMo Kα
b = 8.851 (2) ŵ = 0.69 mm−1
c = 21.875 (4) ÅT = 295 (2) K
α = 92.05 (3)º0.34 × 0.25 × 0.19 mm
β = 99.78 (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 = 0.799, Tmax = 0.880Rint = 0.049
15351 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05315 restraints
wR(F2) = 0.174H atoms treated by a mixture of
independent and constrained refinement
S = 1.14Δρmax = 0.78 e Å−3
7032 reflectionsΔρmin = −0.74 e Å−3
432 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.00000.50000.50000.02982 (19)
Ni20.50000.00000.50000.02956 (19)
O1W0.0183 (3)0.7333 (3)0.48051 (12)0.0373 (6)
H1W1−0.054 (4)0.715 (5)0.4469 (11)0.056*
H1W20.104 (3)0.813 (3)0.4787 (17)0.056*
O2W−0.1773 (3)0.5045 (3)0.55378 (13)0.0374 (6)
H2W1−0.266 (3)0.423 (3)0.548 (2)0.056*
H2W2−0.203 (5)0.588 (2)0.550 (2)0.056*
O3W0.3556 (4)−0.0891 (3)0.56486 (13)0.0425 (7)
H3W10.329 (5)−0.021 (3)0.5854 (19)0.064*
H3W20.295 (5)−0.1834 (18)0.569 (2)0.064*
O4W0.5285 (3)0.2437 (3)0.53314 (12)0.0333 (6)
H4W10.449 (3)0.251 (5)0.5061 (12)0.050*
H4W20.497 (4)0.218 (5)0.5668 (10)0.050*
O5W−0.3714 (5)−0.1696 (4)0.36447 (13)0.0526 (8)
H5W1−0.420 (6)−0.176 (6)0.3269 (9)0.079*
H5W2−0.313 (6)−0.231 (5)0.3679 (19)0.079*
O1−0.2010 (3)0.3951 (3)0.42308 (11)0.0307 (6)
O2−0.2224 (4)0.6112 (3)0.38158 (13)0.0524 (8)
O3−0.4238 (5)−0.1841 (4)0.23630 (14)0.0631 (10)
O40.2831 (3)−0.0170 (3)0.43855 (12)0.0388 (6)
O50.2942 (4)0.2352 (3)0.43586 (12)0.0402 (6)
O60.1073 (5)−0.1320 (4)0.08882 (14)0.0726 (11)
C1−0.2702 (5)0.4638 (4)0.38376 (16)0.0315 (8)
C2−0.4235 (5)0.3574 (4)0.33630 (15)0.0315 (8)
H2−0.48090.26350.35640.038*
C3−0.5476 (5)0.4426 (5)0.31537 (18)0.0419 (10)
H3A−0.58000.48130.35110.063*
H3B−0.64540.36930.28850.063*
H3C−0.49630.53140.29320.063*
C4−0.3642 (5)0.2982 (4)0.28058 (16)0.0332 (8)
C5−0.4119 (5)0.1371 (4)0.26247 (16)0.0327 (8)
H5−0.47750.06330.28500.039*
C6−0.3628 (5)0.0826 (5)0.21024 (17)0.0385 (9)
C7−0.2675 (6)0.1917 (5)0.17658 (19)0.0492 (11)
H7−0.23760.15630.14120.059*
C8−0.2167 (7)0.3521 (5)0.1949 (2)0.0621 (14)
H8−0.14920.42580.17280.074*
C9−0.2661 (6)0.4049 (5)0.2466 (2)0.0501 (11)
H9−0.23240.51430.25850.060*
C10−0.3988 (5)−0.0920 (5)0.19615 (18)0.0408 (10)
C11−0.3997 (6)−0.1565 (5)0.13194 (19)0.0445 (10)
C12−0.4931 (7)−0.1245 (6)0.0799 (2)0.0632 (14)
H12−0.5546−0.05630.08370.076*
C13−0.4960 (9)−0.1930 (7)0.0220 (2)0.0818 (19)
H13−0.5623−0.1734−0.01300.098*
C14−0.4026 (10)−0.2894 (7)0.0156 (3)0.087 (2)
H14−0.4022−0.3323−0.02380.105*
C15−0.3110 (9)−0.3221 (7)0.0665 (3)0.0822 (19)
H15−0.2477−0.38820.06200.099*
C16−0.3097 (7)−0.2590 (6)0.1254 (2)0.0602 (13)
H16−0.2489−0.28510.16040.072*
C170.2332 (5)0.0918 (4)0.41577 (16)0.0326 (8)
C180.0788 (5)0.0336 (5)0.36172 (17)0.0417 (10)
H18−0.0072−0.04920.37790.050*
C190.0037 (6)0.1592 (6)0.3454 (2)0.0547 (12)
H19A−0.02730.19740.38160.082*
H19B−0.09450.11510.31320.082*
H19C0.08420.24670.33090.082*
C200.1152 (5)−0.0518 (5)0.30667 (17)0.0385 (9)
C210.1131 (5)0.0027 (5)0.24809 (17)0.0388 (9)
H210.09410.09920.24210.047*
C220.1386 (5)−0.0820 (5)0.19768 (18)0.0394 (9)
C230.1690 (6)−0.2258 (5)0.2073 (2)0.0513 (12)
H230.1865−0.28470.17470.062*
C240.1727 (7)−0.2792 (5)0.2655 (2)0.0572 (13)
H240.1937−0.37470.27180.069*
C250.1461 (6)−0.1956 (5)0.3148 (2)0.0495 (11)
H250.1489−0.23520.35360.059*
C260.1263 (6)−0.0346 (5)0.13258 (19)0.0492 (11)
C270.1325 (6)0.1312 (5)0.11962 (17)0.0441 (10)
C280.2545 (6)0.2649 (5)0.15325 (19)0.0510 (11)
H280.33030.25250.18690.061*
C290.2646 (7)0.4157 (6)0.1374 (2)0.0633 (14)
H290.34850.50500.15970.076*
C300.1523 (8)0.4347 (7)0.0891 (2)0.0710 (16)
H300.15790.53740.07920.085*
C310.0293 (7)0.3025 (6)0.0546 (2)0.0621 (14)
H31−0.04730.31600.02150.074*
C320.0214 (6)0.1525 (6)0.06945 (18)0.0545 (12)
H32−0.05940.06340.04570.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0269 (4)0.0246 (3)0.0340 (4)0.0048 (3)0.0027 (3)0.0027 (3)
Ni20.0262 (4)0.0252 (3)0.0336 (4)0.0051 (3)0.0029 (3)0.0031 (3)
O1W0.0306 (16)0.0254 (12)0.0461 (15)−0.0004 (11)−0.0008 (12)0.0090 (11)
O2W0.0320 (15)0.0278 (13)0.0512 (16)0.0068 (11)0.0119 (12)−0.0005 (12)
O3W0.0550 (19)0.0256 (13)0.0459 (16)0.0042 (13)0.0253 (13)0.0047 (12)
O4W0.0323 (15)0.0258 (12)0.0385 (14)0.0057 (11)0.0063 (11)0.0013 (11)
O5W0.079 (3)0.0448 (17)0.0418 (16)0.0346 (17)0.0068 (15)−0.0009 (14)
O10.0274 (14)0.0263 (12)0.0338 (13)0.0072 (10)−0.0031 (10)0.0036 (10)
O20.053 (2)0.0290 (14)0.0599 (18)0.0078 (13)−0.0205 (15)0.0109 (13)
O30.108 (3)0.0454 (17)0.0456 (18)0.0350 (19)0.0218 (18)0.0069 (15)
O40.0310 (15)0.0298 (13)0.0482 (15)0.0096 (11)−0.0108 (12)0.0042 (12)
O50.0396 (16)0.0349 (14)0.0448 (15)0.0143 (12)0.0005 (12)0.0057 (12)
O60.111 (3)0.068 (2)0.0395 (17)0.036 (2)0.0074 (18)−0.0136 (17)
C10.031 (2)0.0272 (17)0.0331 (18)0.0061 (15)0.0053 (15)0.0014 (15)
C20.030 (2)0.0313 (18)0.0288 (17)0.0076 (15)0.0005 (14)0.0008 (15)
C30.036 (2)0.043 (2)0.043 (2)0.0148 (18)−0.0045 (17)−0.0045 (18)
C40.031 (2)0.0343 (19)0.0303 (18)0.0085 (16)0.0012 (15)0.0004 (16)
C50.034 (2)0.0369 (19)0.0276 (17)0.0139 (17)0.0031 (15)0.0030 (15)
C60.036 (2)0.041 (2)0.036 (2)0.0106 (18)0.0050 (16)0.0010 (17)
C70.061 (3)0.048 (2)0.040 (2)0.016 (2)0.020 (2)0.0010 (19)
C80.078 (4)0.046 (3)0.055 (3)0.001 (2)0.032 (3)0.003 (2)
C90.057 (3)0.036 (2)0.050 (2)0.004 (2)0.015 (2)−0.0025 (19)
C100.048 (3)0.040 (2)0.037 (2)0.0189 (19)0.0065 (18)−0.0008 (18)
C110.052 (3)0.034 (2)0.046 (2)0.0088 (19)0.017 (2)−0.0015 (18)
C120.082 (4)0.064 (3)0.045 (3)0.027 (3)0.011 (2)0.005 (2)
C130.114 (6)0.075 (4)0.042 (3)0.019 (4)0.004 (3)0.002 (3)
C140.132 (6)0.058 (3)0.057 (3)0.002 (4)0.040 (4)−0.017 (3)
C150.100 (5)0.065 (3)0.086 (4)0.023 (3)0.046 (4)−0.015 (3)
C160.069 (4)0.050 (3)0.065 (3)0.023 (3)0.017 (3)−0.005 (2)
C170.028 (2)0.039 (2)0.0315 (18)0.0110 (17)0.0079 (15)0.0015 (16)
C180.046 (3)0.047 (2)0.0324 (19)0.021 (2)−0.0003 (17)0.0012 (18)
C190.045 (3)0.070 (3)0.051 (3)0.028 (2)−0.002 (2)−0.005 (2)
C200.039 (2)0.041 (2)0.035 (2)0.0182 (18)−0.0020 (16)−0.0017 (17)
C210.038 (2)0.039 (2)0.038 (2)0.0160 (18)−0.0001 (17)−0.0057 (17)
C220.037 (2)0.039 (2)0.039 (2)0.0131 (18)0.0003 (17)−0.0053 (18)
C230.057 (3)0.051 (3)0.048 (2)0.026 (2)0.002 (2)−0.008 (2)
C240.073 (4)0.045 (2)0.058 (3)0.031 (2)0.002 (2)−0.007 (2)
C250.059 (3)0.046 (2)0.044 (2)0.023 (2)0.002 (2)0.003 (2)
C260.049 (3)0.054 (3)0.040 (2)0.013 (2)0.0041 (19)−0.009 (2)
C270.048 (3)0.051 (2)0.031 (2)0.016 (2)0.0046 (17)−0.0027 (18)
C280.054 (3)0.056 (3)0.037 (2)0.016 (2)−0.0021 (19)−0.002 (2)
C290.081 (4)0.053 (3)0.048 (3)0.014 (3)0.011 (2)0.000 (2)
C300.118 (5)0.064 (3)0.047 (3)0.045 (3)0.028 (3)0.015 (2)
C310.081 (4)0.077 (3)0.036 (2)0.040 (3)0.004 (2)0.004 (2)
C320.059 (3)0.071 (3)0.031 (2)0.023 (3)0.0002 (19)−0.006 (2)
Geometric parameters (Å, °) top
Ni1—O2W2.081 (3)C8—H80.9300
Ni1—O1W2.085 (2)C9—H90.9300
Ni1—O12.127 (2)C10—C111.495 (5)
Ni2—O3W2.051 (3)C11—C121.370 (6)
Ni2—O42.057 (2)C11—C161.384 (6)
Ni2—O4W2.174 (2)C12—C131.377 (7)
Ni1—O2Wi2.081 (3)C12—H120.9300
Ni1—O1Wi2.085 (2)C13—C141.363 (9)
Ni1—O1i2.127 (2)C13—H130.9300
Ni2—O3Wii2.051 (3)C14—C151.347 (9)
Ni2—O4ii2.057 (2)C14—H140.9300
Ni2—O4Wii2.174 (2)C15—C161.383 (7)
O1W—H1W10.85 (3)C15—H150.9300
O1W—H1W20.85 (3)C16—H160.9300
O2W—H2W10.85 (3)C17—C181.547 (5)
O2W—H2W20.84 (3)C18—C191.480 (6)
O3W—H3W10.85 (4)C18—C201.528 (5)
O3W—H3W20.85 (4)C18—H180.9800
O4W—H4W10.84 (3)C19—H19A0.9600
O4W—H4W20.84 (3)C19—H19B0.9600
O5W—H5W10.85 (2)C19—H19C0.9600
O5W—H5W20.85 (5)C20—C211.384 (5)
O1—C11.248 (4)C20—C251.393 (6)
O2—C11.240 (4)C21—C221.398 (5)
O3—C101.218 (5)C21—H210.9300
O4—C171.260 (4)C22—C231.395 (6)
O5—C171.237 (4)C22—C261.495 (6)
O6—C261.218 (5)C23—C241.372 (6)
C1—C21.534 (5)C23—H230.9300
C2—C31.512 (5)C24—C251.378 (6)
C2—C41.534 (5)C24—H240.9300
C2—H20.9800C25—H250.9300
C3—H3A0.9600C26—C271.490 (6)
C3—H3B0.9600C27—C281.381 (6)
C3—H3C0.9600C27—C321.386 (6)
C4—C51.373 (5)C28—C291.370 (7)
C4—C91.378 (6)C28—H280.9300
C5—C61.403 (5)C29—C301.357 (7)
C5—H50.9300C29—H290.9300
C6—C71.372 (6)C30—C311.385 (8)
C6—C101.484 (5)C30—H300.9300
C7—C81.366 (6)C31—C321.361 (7)
C7—H70.9300C31—H310.9300
C8—C91.388 (6)C32—H320.9300
O2W—Ni1—O1W88.29 (11)C8—C9—H9119.4
O2W—Ni1—O1Wi91.71 (11)O3—C10—C6121.4 (3)
O2W—Ni1—O188.56 (10)O3—C10—C11118.9 (3)
O1W—Ni1—O193.12 (10)C6—C10—C11119.7 (4)
O2W—Ni1—O1i91.44 (10)C12—C11—C16119.1 (4)
O1W—Ni1—O1i86.88 (10)C12—C11—C10122.3 (4)
O3W—Ni2—O4ii91.44 (12)C16—C11—C10118.5 (4)
O3W—Ni2—O488.56 (12)C11—C12—C13120.1 (5)
O3W—Ni2—O4W90.55 (10)C11—C12—H12119.9
O4—Ni2—O4W90.65 (10)C13—C12—H12119.9
O3W—Ni2—O4Wii89.45 (10)C14—C13—C12120.6 (6)
O4—Ni2—O4Wii89.35 (10)C14—C13—H13119.7
O2Wi—Ni1—O2W180.000 (1)C12—C13—H13119.7
O2Wi—Ni1—O1W91.71 (11)C15—C14—C13119.7 (5)
O2Wi—Ni1—O1Wi88.29 (11)C15—C14—H14120.2
O1W—Ni1—O1Wi180.000 (1)C13—C14—H14120.2
O2Wi—Ni1—O191.44 (10)C14—C15—C16121.0 (6)
O1Wi—Ni1—O186.88 (10)C14—C15—H15119.5
O2Wi—Ni1—O1i88.56 (10)C16—C15—H15119.5
O1Wi—Ni1—O1i93.12 (10)C15—C16—C11119.4 (5)
O1—Ni1—O1i180.000 (1)C15—C16—H16120.3
O3Wii—Ni2—O3W180.000 (1)C11—C16—H16120.3
O3Wii—Ni2—O4ii88.56 (12)O5—C17—O4124.2 (3)
O3Wii—Ni2—O491.44 (12)O5—C17—C18120.4 (3)
O4ii—Ni2—O4180.000 (1)O4—C17—C18115.3 (3)
O3Wii—Ni2—O4W89.45 (10)C19—C18—C20115.0 (3)
O4ii—Ni2—O4W89.35 (10)C19—C18—C17113.1 (3)
O3Wii—Ni2—O4Wii90.55 (10)C20—C18—C17111.6 (3)
O4ii—Ni2—O4Wii90.65 (10)C19—C18—H18105.4
O4W—Ni2—O4Wii180.000 (1)C20—C18—H18105.4
Ni1—O1W—H1W1101 (3)C17—C18—H18105.4
Ni1—O1W—H1W2130 (3)C18—C19—H19A109.5
H1W1—O1W—H1W2111 (4)C18—C19—H19B109.5
Ni1—O2W—H2W1116 (3)H19A—C19—H19B109.5
Ni1—O2W—H2W2111 (3)C18—C19—H19C109.5
H2W1—O2W—H2W2110 (3)H19A—C19—H19C109.5
Ni2—O3W—H3W1116 (3)H19B—C19—H19C109.5
Ni2—O3W—H3W2131 (3)C21—C20—C25117.7 (4)
H3W1—O3W—H3W2110 (4)C21—C20—C18123.6 (3)
Ni2—O4W—H4W195 (3)C25—C20—C18118.6 (4)
Ni2—O4W—H4W294 (3)C20—C21—C22122.5 (4)
H4W1—O4W—H4W2111 (4)C20—C21—H21118.8
H5W1—O5W—H5W2110 (4)C22—C21—H21118.8
C1—O1—Ni1128.4 (2)C23—C22—C21118.4 (4)
C17—O4—Ni2130.0 (2)C23—C22—C26116.9 (4)
O2—C1—O1123.7 (3)C21—C22—C26124.7 (4)
O2—C1—C2119.2 (3)C24—C23—C22119.3 (4)
O1—C1—C2117.1 (3)C24—C23—H23120.4
C3—C2—C1112.2 (3)C22—C23—H23120.4
C3—C2—C4111.2 (3)C23—C24—C25122.0 (4)
C1—C2—C4109.4 (3)C23—C24—H24119.0
C3—C2—H2108.0C25—C24—H24119.0
C1—C2—H2108.0C24—C25—C20120.2 (4)
C4—C2—H2108.0C24—C25—H25119.9
C2—C3—H3A109.5C20—C25—H25119.9
C2—C3—H3B109.5O6—C26—C27118.6 (4)
H3A—C3—H3B109.5O6—C26—C22120.5 (4)
C2—C3—H3C109.5C27—C26—C22120.9 (3)
H3A—C3—H3C109.5C28—C27—C32118.8 (4)
H3B—C3—H3C109.5C28—C27—C26121.8 (4)
C5—C4—C9118.5 (3)C32—C27—C26119.2 (4)
C5—C4—C2120.5 (3)C29—C28—C27120.5 (4)
C9—C4—C2121.0 (3)C29—C28—H28119.7
C4—C5—C6120.7 (4)C27—C28—H28119.7
C4—C5—H5119.7C30—C29—C28120.0 (5)
C6—C5—H5119.7C30—C29—H29120.0
C7—C6—C5119.6 (4)C28—C29—H29120.0
C7—C6—C10120.6 (4)C29—C30—C31120.5 (5)
C5—C6—C10119.4 (4)C29—C30—H30119.7
C8—C7—C6120.2 (4)C31—C30—H30119.7
C8—C7—H7119.9C32—C31—C30119.5 (5)
C6—C7—H7119.9C32—C31—H31120.2
C7—C8—C9119.8 (4)C30—C31—H31120.2
C7—C8—H8120.1C31—C32—C27120.6 (4)
C9—C8—H8120.1C31—C32—H32119.7
C4—C9—C8121.3 (4)C27—C32—H32119.7
C4—C9—H9119.4
O2Wi—Ni1—O1—C1−91.4 (3)C13—C14—C15—C16−0.2 (10)
O2W—Ni1—O1—C188.6 (3)C14—C15—C16—C11−2.1 (9)
O1W—Ni1—O1—C10.4 (3)C12—C11—C16—C152.3 (8)
O1Wi—Ni1—O1—C1−179.6 (3)C10—C11—C16—C15178.9 (5)
O3Wii—Ni2—O4—C17−67.2 (3)Ni2—O4—C17—O5−14.4 (6)
O3W—Ni2—O4—C17112.8 (3)Ni2—O4—C17—C18169.2 (3)
O4W—Ni2—O4—C1722.3 (3)O5—C17—C18—C19−8.5 (6)
O4Wii—Ni2—O4—C17−157.7 (3)O4—C17—C18—C19168.1 (4)
Ni1—O1—C1—O24.7 (6)O5—C17—C18—C20123.0 (4)
Ni1—O1—C1—C2−174.8 (2)O4—C17—C18—C20−60.5 (5)
O2—C1—C2—C3−29.9 (5)C19—C18—C20—C2113.1 (6)
O1—C1—C2—C3149.7 (3)C17—C18—C20—C21−117.4 (4)
O2—C1—C2—C494.0 (4)C19—C18—C20—C25−164.4 (4)
O1—C1—C2—C4−86.4 (4)C17—C18—C20—C2565.1 (5)
C3—C2—C4—C5−110.6 (4)C25—C20—C21—C220.8 (6)
C1—C2—C4—C5124.9 (4)C18—C20—C21—C22−176.7 (4)
C3—C2—C4—C967.6 (5)C20—C21—C22—C23−0.7 (6)
C1—C2—C4—C9−57.0 (5)C20—C21—C22—C26175.7 (4)
C9—C4—C5—C6−0.4 (6)C21—C22—C23—C240.1 (7)
C2—C4—C5—C6177.8 (3)C26—C22—C23—C24−176.6 (4)
C4—C5—C6—C7−0.7 (6)C22—C23—C24—C250.4 (8)
C4—C5—C6—C10172.8 (4)C23—C24—C25—C20−0.3 (8)
C5—C6—C7—C81.9 (7)C21—C20—C25—C24−0.3 (7)
C10—C6—C7—C8−171.5 (4)C18—C20—C25—C24177.4 (4)
C6—C7—C8—C9−2.0 (8)C23—C22—C26—O615.3 (7)
C5—C4—C9—C80.3 (7)C21—C22—C26—O6−161.2 (4)
C2—C4—C9—C8−177.9 (4)C23—C22—C26—C27−166.2 (4)
C7—C8—C9—C40.9 (8)C21—C22—C26—C2717.3 (7)
C7—C6—C10—O3151.8 (5)O6—C26—C27—C28−133.4 (5)
C5—C6—C10—O3−21.6 (6)C22—C26—C27—C2848.1 (7)
C7—C6—C10—C11−26.3 (6)O6—C26—C27—C3241.5 (7)
C5—C6—C10—C11160.3 (4)C22—C26—C27—C32−137.0 (4)
O3—C10—C11—C12129.5 (5)C32—C27—C28—C290.3 (7)
C6—C10—C11—C12−52.4 (6)C26—C27—C28—C29175.3 (5)
O3—C10—C11—C16−47.0 (6)C27—C28—C29—C301.3 (8)
C6—C10—C11—C16131.1 (4)C28—C29—C30—C31−1.6 (8)
C16—C11—C12—C13−0.4 (8)C29—C30—C31—C320.1 (8)
C10—C11—C12—C13−176.8 (5)C30—C31—C32—C271.5 (8)
C11—C12—C13—C14−1.9 (9)C28—C27—C32—C31−1.7 (7)
C12—C13—C14—C152.2 (10)C26—C27—C32—C31−176.8 (4)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O20.85 (3)1.82 (3)2.640 (4)162 (4)
O2W—H2W1···O4Wiii0.85 (3)1.92 (3)2.766 (4)177 (4)
O2W—H2W2···O5i0.84 (3)1.99 (3)2.809 (4)162 (4)
O3W—H3W1···O5Wiv0.85 (4)1.88 (4)2.669 (4)155 (4)
O3W—H3W2···O1iv0.85 (4)1.812 (17)2.647 (4)169 (4)
O4W—H4W1···O50.84 (3)1.82 (3)2.645 (4)166 (4)
O4W—H4W2···O5Wiv0.84 (3)1.97 (3)2.795 (4)166 (3)
O5W—H5W1···O30.85 (2)1.98 (3)2.755 (4)152 (5)
O5W—H5W2···O2v0.85 (5)1.82 (5)2.651 (4)168 (6)
Symmetry codes: (iii) x−1, y, z; (i) −x, −y+1, −z+1; (iv) −x, −y, −z+1; (v) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O20.85 (3)1.82 (3)2.640 (4)162 (4)
O2W—H2W1···O4Wi0.85 (3)1.92 (3)2.766 (4)177 (4)
O2W—H2W2···O5ii0.84 (3)1.99 (3)2.809 (4)162 (4)
O3W—H3W1···O5Wiii0.85 (4)1.88 (4)2.669 (4)155 (4)
O3W—H3W2···O1iii0.85 (4)1.812 (17)2.647 (4)169 (4)
O4W—H4W1···O50.84 (3)1.82 (3)2.645 (4)166 (4)
O4W—H4W2···O5Wiii0.84 (3)1.97 (3)2.795 (4)166 (3)
O5W—H5W1···O30.85 (2)1.98 (3)2.755 (4)152 (5)
O5W—H5W2···O2iv0.85 (5)1.82 (5)2.651 (4)168 (6)
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) −x, −y, −z+1; (iv) x, y−1, z.
Acknowledgements top

The authors thank Harbin Medical University for supporting this work.

references
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