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The crystal structure of the title compound, [Ni(C7H5O4)(C12H8N2)2(H2O)](C7H5O4)·H2O, consists of NiII complex cations, 2,4-dihydroxy­benzoate (dHBA) anions and solvent water mol­ecules. The NiII complex cation assumes a distorted octa­hedral coordination geometry formed by two 1,10-phenanthroline (phen) ligands, one dHBA ion and a water mol­ecule. π–π Stacking is observed between partially overlapped, parallel phen ligands and between a nearly parallel phen ligand and benzene ring of dHBA.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603772X/ng2097sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603772X/ng2097Isup2.hkl
Contains datablock I

CCDC reference: 624932

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.038
  • wR factor = 0.097
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Aqua(2,4-dihydroxybenzoato-κO1)bis(1,10-phenanthroline-κ2N,N')nickel(II) 2,4-dihydroxybenzoate monohydrate top
Crystal data top
[Ni(C7H5O4)(C12H8N2)2(H2O)](C7H5O4)·H2OZ = 2
Mr = 761.37F(000) = 788
Triclinic, P1Dx = 1.490 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.347 (4) ÅCell parameters from 3600 reflections
b = 13.408 (6) Åθ = 3.0–23.0°
c = 13.578 (6) ŵ = 0.64 mm1
α = 118.829 (14)°T = 295 K
β = 90.106 (14)°Prism, green
γ = 116.327 (13)°0.35 × 0.19 × 0.13 mm
V = 1697.1 (13) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
7612 independent reflections
Radiation source: fine-focus sealed tube5990 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = 1615
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1717
Tmin = 0.785, Tmax = 0.920l = 1717
16731 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0494P)2 + 0.1081P]
where P = (Fo2 + 2Fc2)/3
7612 reflections(Δ/σ)max = 0.001
482 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.29 e Å3
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
Ni0.311102 (19)0.56630 (2)0.756762 (19)0.03817 (8)
O10.25627 (12)0.39229 (12)0.59853 (11)0.0489 (3)
O20.15371 (14)0.23226 (13)0.63157 (12)0.0607 (4)
O90.24175 (16)0.45999 (15)0.83154 (13)0.0703 (4)
H9A0.19710.36650.77090.114 (10)*
H9B0.23780.47650.90840.093 (9)*
O30.27797 (14)0.34334 (13)0.39826 (13)0.0608 (4)
H30.28010.38560.48170.091*
O1W0.97228 (17)0.33608 (15)0.97300 (14)0.0766 (5)
H1A0.93100.34080.91420.092 (9)*
H1B1.05560.39430.98960.087 (9)*
O40.09673 (16)0.09748 (15)0.08634 (12)0.0712 (4)
H40.07010.18020.07140.107*
O50.78510 (16)0.47694 (17)0.95945 (13)0.0817 (5)
O60.80850 (16)0.31543 (19)0.82086 (15)0.0831 (5)
O70.62476 (17)0.11133 (17)0.65295 (13)0.0766 (5)
H70.70920.17680.70260.115*
O80.22723 (16)0.06702 (17)0.62990 (16)0.0855 (6)
H80.19580.12520.65370.128*
N10.49046 (14)0.60144 (16)0.80208 (14)0.0457 (4)
N20.38624 (13)0.74551 (14)0.91946 (12)0.0423 (3)
N30.35782 (13)0.65592 (14)0.65969 (12)0.0390 (3)
N40.14685 (13)0.56518 (14)0.72147 (13)0.0415 (3)
C10.5383 (2)0.5259 (2)0.7444 (2)0.0559 (5)
H10.48830.44690.67340.067*
C20.6604 (2)0.5603 (3)0.7859 (3)0.0692 (7)
H20.69040.50410.74360.083*
C30.7353 (2)0.6756 (3)0.8880 (2)0.0707 (7)
H110.81730.69930.91570.085*
C40.68908 (18)0.7600 (2)0.9527 (2)0.0591 (6)
C50.7600 (2)0.8847 (3)1.0610 (2)0.0777 (8)
H50.84380.91601.09160.093*
C60.7080 (2)0.9575 (3)1.1193 (2)0.0766 (7)
H60.75661.03811.18930.092*
C70.5794 (2)0.9137 (2)1.07594 (18)0.0562 (5)
C80.5176 (2)0.9812 (2)1.13518 (18)0.0663 (6)
H120.56091.06031.20740.080*
C90.3953 (2)0.9318 (2)1.08791 (18)0.0631 (6)
H90.35390.97631.12710.076*
C100.33197 (19)0.81267 (19)0.97901 (17)0.0512 (5)
H100.24790.77920.94710.061*
C110.50849 (17)0.79412 (18)0.96779 (16)0.0449 (4)
C120.56382 (17)0.7168 (2)0.90551 (17)0.0463 (4)
C130.46180 (18)0.69756 (19)0.62733 (18)0.0498 (4)
H130.52630.68790.64910.060*
C140.4787 (2)0.7551 (2)0.5622 (2)0.0599 (5)
H140.55310.78290.54100.072*
C150.3857 (2)0.7703 (2)0.52973 (19)0.0592 (5)
H150.39560.80780.48550.071*
C160.27425 (19)0.72908 (19)0.56359 (16)0.0494 (4)
C170.1727 (2)0.7466 (2)0.5388 (2)0.0617 (6)
H170.17820.78550.49650.074*
C180.0699 (2)0.7074 (2)0.5763 (2)0.0632 (6)
H180.00650.72170.56060.076*
C190.05575 (18)0.6448 (2)0.63923 (18)0.0521 (5)
C200.04936 (19)0.6005 (2)0.6801 (2)0.0648 (6)
H200.11540.61280.66760.078*
C210.05433 (19)0.5402 (2)0.7374 (2)0.0651 (6)
H210.12390.51040.76400.078*
C220.04490 (17)0.5227 (2)0.75640 (18)0.0522 (5)
H220.03960.47980.79490.063*
C230.15280 (16)0.62518 (17)0.66384 (15)0.0418 (4)
C240.26448 (16)0.67114 (16)0.62751 (14)0.0398 (4)
C250.19293 (16)0.26995 (17)0.56450 (16)0.0421 (4)
C260.16917 (15)0.17379 (17)0.43909 (15)0.0400 (4)
C270.21037 (17)0.21327 (18)0.36149 (16)0.0435 (4)
C280.1854 (2)0.1216 (2)0.24484 (17)0.0539 (5)
H280.21340.14990.19450.065*
C290.11879 (19)0.0125 (2)0.20187 (16)0.0503 (5)
C300.07776 (19)0.05419 (19)0.27731 (17)0.0562 (5)
H300.03370.14380.24950.067*
C310.10259 (18)0.03776 (19)0.39345 (17)0.0522 (5)
H310.07430.00880.44330.063*
C320.7415 (2)0.3645 (2)0.86803 (18)0.0636 (6)
C330.6048 (2)0.2867 (2)0.80770 (17)0.0561 (5)
C340.5529 (2)0.1638 (2)0.70197 (17)0.0587 (5)
C350.4276 (2)0.0949 (2)0.64385 (19)0.0640 (6)
H350.39490.01460.57270.077*
C360.3508 (2)0.1435 (2)0.6898 (2)0.0629 (6)
C370.3993 (2)0.2650 (2)0.7951 (2)0.0663 (6)
H370.34780.29910.82620.080*
C380.5251 (2)0.3337 (2)0.85224 (18)0.0623 (6)
H380.55760.41440.92300.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.04080 (13)0.03646 (13)0.03941 (13)0.02207 (10)0.01396 (9)0.01963 (10)
O10.0615 (8)0.0363 (7)0.0449 (7)0.0231 (6)0.0202 (6)0.0206 (6)
O20.0806 (10)0.0437 (7)0.0495 (8)0.0239 (7)0.0264 (7)0.0264 (7)
O90.1140 (13)0.0475 (8)0.0504 (8)0.0381 (9)0.0375 (8)0.0296 (7)
O30.0845 (10)0.0423 (7)0.0550 (8)0.0268 (7)0.0269 (7)0.0306 (7)
O1W0.0793 (12)0.0515 (9)0.0688 (10)0.0200 (9)0.0058 (9)0.0243 (8)
O40.1009 (12)0.0551 (9)0.0419 (7)0.0346 (9)0.0205 (8)0.0203 (7)
O50.0835 (11)0.0640 (10)0.0480 (8)0.0115 (9)0.0114 (8)0.0208 (8)
O60.0732 (11)0.0832 (12)0.0692 (11)0.0314 (10)0.0145 (9)0.0329 (10)
O70.0854 (12)0.0745 (11)0.0532 (9)0.0428 (10)0.0159 (8)0.0215 (8)
O80.0795 (12)0.0614 (10)0.0946 (13)0.0317 (9)0.0037 (10)0.0319 (10)
N10.0487 (9)0.0541 (9)0.0514 (9)0.0334 (8)0.0206 (7)0.0331 (8)
N20.0456 (8)0.0401 (8)0.0402 (8)0.0231 (7)0.0119 (7)0.0196 (7)
N30.0392 (7)0.0353 (7)0.0415 (7)0.0199 (6)0.0131 (6)0.0191 (6)
N40.0376 (7)0.0406 (8)0.0417 (8)0.0191 (6)0.0121 (6)0.0198 (7)
C10.0620 (12)0.0649 (13)0.0703 (13)0.0438 (11)0.0326 (11)0.0455 (11)
C20.0663 (14)0.0905 (18)0.107 (2)0.0577 (14)0.0495 (14)0.0738 (17)
C30.0491 (12)0.103 (2)0.106 (2)0.0454 (14)0.0333 (13)0.0804 (18)
C40.0462 (11)0.0791 (15)0.0746 (14)0.0285 (11)0.0188 (10)0.0591 (13)
C50.0453 (13)0.0905 (19)0.0836 (17)0.0151 (13)0.0016 (12)0.0553 (16)
C60.0608 (15)0.0672 (15)0.0639 (14)0.0060 (12)0.0070 (12)0.0342 (13)
C70.0576 (12)0.0474 (11)0.0475 (10)0.0130 (9)0.0057 (9)0.0273 (9)
C80.0832 (17)0.0417 (11)0.0441 (11)0.0198 (11)0.0110 (11)0.0142 (9)
C90.0822 (16)0.0480 (11)0.0511 (11)0.0362 (12)0.0257 (11)0.0186 (10)
C100.0582 (11)0.0470 (11)0.0457 (10)0.0302 (9)0.0182 (9)0.0200 (9)
C110.0465 (10)0.0444 (10)0.0438 (9)0.0187 (8)0.0105 (8)0.0275 (8)
C120.0445 (10)0.0560 (11)0.0536 (11)0.0254 (9)0.0170 (9)0.0395 (10)
C130.0483 (10)0.0485 (11)0.0580 (11)0.0263 (9)0.0230 (9)0.0307 (9)
C140.0648 (13)0.0595 (13)0.0677 (13)0.0330 (11)0.0366 (11)0.0408 (11)
C150.0795 (14)0.0534 (12)0.0560 (12)0.0332 (11)0.0261 (11)0.0375 (10)
C160.0585 (11)0.0405 (10)0.0430 (10)0.0223 (9)0.0084 (9)0.0211 (8)
C170.0740 (15)0.0575 (13)0.0608 (13)0.0338 (11)0.0069 (11)0.0362 (11)
C180.0598 (13)0.0658 (14)0.0677 (14)0.0368 (12)0.0045 (11)0.0340 (12)
C190.0444 (10)0.0492 (11)0.0523 (11)0.0244 (9)0.0042 (9)0.0200 (9)
C200.0426 (11)0.0751 (15)0.0725 (14)0.0342 (11)0.0133 (10)0.0332 (13)
C210.0436 (11)0.0820 (16)0.0739 (15)0.0335 (11)0.0268 (11)0.0433 (13)
C220.0423 (10)0.0572 (12)0.0554 (11)0.0233 (9)0.0180 (9)0.0310 (10)
C230.0375 (9)0.0363 (9)0.0385 (9)0.0177 (7)0.0050 (7)0.0125 (7)
C240.0427 (9)0.0336 (8)0.0358 (8)0.0184 (7)0.0081 (7)0.0148 (7)
C250.0419 (9)0.0395 (9)0.0457 (9)0.0214 (8)0.0162 (8)0.0228 (8)
C260.0387 (9)0.0379 (9)0.0429 (9)0.0193 (7)0.0149 (7)0.0214 (8)
C270.0463 (10)0.0390 (9)0.0495 (10)0.0231 (8)0.0165 (8)0.0255 (8)
C280.0696 (13)0.0520 (11)0.0471 (10)0.0300 (10)0.0232 (10)0.0319 (9)
C290.0576 (11)0.0486 (11)0.0402 (9)0.0275 (9)0.0143 (9)0.0206 (8)
C300.0642 (12)0.0348 (9)0.0503 (11)0.0155 (9)0.0173 (10)0.0188 (9)
C310.0593 (11)0.0416 (10)0.0482 (10)0.0187 (9)0.0227 (9)0.0254 (9)
C320.0718 (14)0.0587 (13)0.0423 (11)0.0167 (11)0.0131 (10)0.0301 (10)
C330.0726 (14)0.0478 (11)0.0414 (10)0.0218 (10)0.0148 (10)0.0276 (9)
C340.0772 (15)0.0516 (12)0.0427 (10)0.0279 (11)0.0147 (10)0.0267 (9)
C350.0797 (16)0.0485 (12)0.0477 (11)0.0269 (12)0.0048 (11)0.0204 (10)
C360.0753 (15)0.0496 (12)0.0608 (13)0.0270 (11)0.0077 (12)0.0320 (11)
C370.0842 (16)0.0567 (13)0.0648 (13)0.0386 (13)0.0240 (12)0.0346 (11)
C380.0850 (16)0.0440 (11)0.0469 (11)0.0263 (11)0.0172 (11)0.0231 (9)
Geometric parameters (Å, º) top
Ni—O12.0681 (15)C8—H120.9300
Ni—O92.0279 (16)C9—C101.400 (3)
Ni—N12.0723 (16)C9—H90.9300
Ni—N22.1002 (17)C10—H100.9300
Ni—N32.1047 (17)C11—C121.428 (3)
Ni—N42.0748 (15)C13—C141.392 (3)
O1—C251.283 (2)C13—H130.9300
O2—C251.244 (2)C14—C151.359 (3)
O9—H9A0.9711C14—H140.9300
O9—H9B0.9625C15—C161.408 (3)
O3—C271.362 (2)C15—H150.9300
O3—H30.9866C16—C241.393 (3)
O1W—H1A0.9879C16—C171.441 (3)
O1W—H1B0.9137C17—C181.347 (3)
O4—C291.354 (2)C17—H170.9300
O4—H40.9158C18—C191.425 (3)
O5—C321.255 (3)C18—H180.9300
O6—C321.268 (3)C19—C231.407 (2)
O7—C341.352 (3)C19—C201.407 (3)
O7—H70.9630C20—C211.352 (3)
O8—C361.358 (3)C20—H200.9300
O8—H80.9429C21—C221.391 (3)
N1—C11.325 (2)C21—H210.9300
N1—C121.358 (3)C22—H220.9300
N2—C101.322 (2)C23—C241.437 (3)
N2—C111.358 (2)C25—C261.481 (3)
N3—C131.325 (2)C26—C271.397 (3)
N3—C241.361 (2)C26—C311.402 (3)
N4—C221.327 (2)C27—C281.378 (3)
N4—C231.349 (2)C28—C291.388 (3)
C1—C21.390 (3)C28—H280.9300
C1—H10.9300C29—C301.386 (3)
C2—C31.352 (4)C30—C311.374 (3)
C2—H20.9300C30—H300.9300
C3—C41.413 (3)C31—H310.9300
C3—H110.9300C32—C331.489 (3)
C4—C121.408 (3)C33—C381.384 (3)
C4—C51.431 (4)C33—C341.402 (3)
C5—C61.342 (4)C34—C351.376 (3)
C5—H50.9300C35—C361.368 (3)
C6—C71.431 (3)C35—H350.9300
C6—H60.9300C36—C371.394 (3)
C7—C81.400 (3)C37—C381.378 (3)
C7—C111.405 (3)C37—H370.9300
C8—C91.353 (3)C38—H380.9300
O9—Ni—O189.00 (7)C15—C14—C13119.5 (2)
O9—Ni—N192.39 (7)C15—C14—H14120.3
O1—Ni—N193.98 (6)C13—C14—H14120.3
O9—Ni—N494.57 (7)C14—C15—C16119.6 (2)
O1—Ni—N493.06 (6)C14—C15—H15120.2
N1—Ni—N4170.18 (6)C16—C15—H15120.2
O9—Ni—N291.80 (7)C24—C16—C15117.23 (18)
O1—Ni—N2173.81 (5)C24—C16—C17118.76 (19)
N1—Ni—N279.85 (6)C15—C16—C17124.0 (2)
N4—Ni—N293.00 (6)C18—C17—C16120.8 (2)
O9—Ni—N3171.54 (6)C18—C17—H17119.6
O1—Ni—N385.28 (7)C16—C17—H17119.6
N1—Ni—N394.21 (6)C17—C18—C19121.75 (19)
N4—Ni—N379.55 (6)C17—C18—H18119.1
N2—Ni—N394.55 (7)C19—C18—H18119.1
C25—O1—Ni133.46 (12)C23—C19—C20116.5 (2)
Ni—O9—H9A109.1C23—C19—C18118.8 (2)
Ni—O9—H9B137.9C20—C19—C18124.69 (19)
H9A—O9—H9B112.9C21—C20—C19119.95 (19)
C27—O3—H3100.9C21—C20—H20120.0
H1A—O1W—H1B103.6C19—C20—H20120.0
C29—O4—H4109.8C20—C21—C22119.8 (2)
C34—O7—H7105.5C20—C21—H21120.1
C36—O8—H8105.7C22—C21—H21120.1
C1—N1—C12118.61 (17)N4—C22—C21122.2 (2)
C1—N1—Ni128.26 (14)N4—C22—H22118.9
C12—N1—Ni113.12 (12)C21—C22—H22118.9
C10—N2—C11118.01 (16)N4—C23—C19122.90 (18)
C10—N2—Ni129.79 (13)N4—C23—C24117.55 (15)
C11—N2—Ni112.19 (12)C19—C23—C24119.55 (18)
C13—N3—C24117.88 (17)N3—C24—C16122.99 (17)
C13—N3—Ni129.57 (13)N3—C24—C23116.70 (16)
C24—N3—Ni112.55 (12)C16—C24—C23120.31 (16)
C22—N4—C23118.52 (16)O2—C25—O1122.94 (17)
C22—N4—Ni127.76 (14)O2—C25—C26121.02 (17)
C23—N4—Ni113.49 (11)O1—C25—C26116.03 (17)
N1—C1—C2122.5 (2)C27—C26—C31117.24 (17)
N1—C1—H1118.8C27—C26—C25122.22 (17)
C2—C1—H1118.8C31—C26—C25120.54 (17)
C3—C2—C1119.8 (2)O3—C27—C28117.52 (18)
C3—C2—H2120.1O3—C27—C26121.44 (16)
C1—C2—H2120.1C28—C27—C26121.04 (18)
C2—C3—C4120.0 (2)C27—C28—C29120.53 (19)
C2—C3—H11120.0C27—C28—H28119.7
C4—C3—H11120.0C29—C28—H28119.7
C12—C4—C3116.6 (2)O4—C29—C30122.79 (19)
C12—C4—C5118.4 (2)O4—C29—C28117.66 (19)
C3—C4—C5124.9 (2)C30—C29—C28119.55 (18)
C6—C5—C4121.4 (2)C31—C30—C29119.60 (19)
C6—C5—H5119.3C31—C30—H30120.2
C4—C5—H5119.3C29—C30—H30120.2
C5—C6—C7121.5 (2)C30—C31—C26122.05 (19)
C5—C6—H6119.3C30—C31—H31119.0
C7—C6—H6119.3C26—C31—H31119.0
C8—C7—C11117.02 (19)O5—C32—O6123.5 (2)
C8—C7—C6124.4 (2)O5—C32—C33118.7 (2)
C11—C7—C6118.6 (2)O6—C32—C33117.7 (2)
C9—C8—C7120.35 (19)C38—C33—C34117.7 (2)
C9—C8—H12119.8C38—C33—C32121.5 (2)
C7—C8—H12119.8C34—C33—C32120.8 (2)
C8—C9—C10118.9 (2)O7—C34—C35118.2 (2)
C8—C9—H9120.5O7—C34—C33121.2 (2)
C10—C9—H9120.5C35—C34—C33120.6 (2)
N2—C10—C9123.02 (19)C36—C35—C34120.5 (2)
N2—C10—H10118.5C36—C35—H35119.7
C9—C10—H10118.5C34—C35—H35119.7
N2—C11—C7122.66 (18)O8—C36—C35117.1 (2)
N2—C11—C12117.38 (16)O8—C36—C37122.7 (2)
C7—C11—C12119.94 (18)C35—C36—C37120.3 (2)
N1—C12—C4122.51 (19)C38—C37—C36118.8 (2)
N1—C12—C11117.40 (16)C38—C37—H37120.6
C4—C12—C11120.07 (19)C36—C37—H37120.6
N3—C13—C14122.86 (18)C37—C38—C33122.1 (2)
N3—C13—H13118.6C37—C38—H38118.9
C14—C13—H13118.6C33—C38—H38118.9
O9—Ni—O1—C256.44 (17)C24—N3—C13—C140.2 (3)
N1—Ni—O1—C2598.76 (17)Ni—N3—C13—C14179.77 (14)
N4—Ni—O1—C2588.09 (17)N3—C13—C14—C150.2 (3)
N3—Ni—O1—C25167.33 (17)C13—C14—C15—C160.7 (3)
O9—Ni—N1—C185.77 (18)C14—C15—C16—C241.4 (3)
O1—Ni—N1—C13.39 (18)C14—C15—C16—C17176.8 (2)
N2—Ni—N1—C1177.17 (18)C24—C16—C17—C180.2 (3)
N3—Ni—N1—C188.95 (18)C15—C16—C17—C18178.4 (2)
O9—Ni—N1—C1293.22 (14)C16—C17—C18—C191.4 (3)
O1—Ni—N1—C12177.63 (13)C17—C18—C19—C230.8 (3)
N2—Ni—N1—C121.81 (12)C17—C18—C19—C20179.5 (2)
N3—Ni—N1—C1292.07 (14)C23—C19—C20—C211.4 (3)
O9—Ni—N2—C1084.40 (18)C18—C19—C20—C21178.9 (2)
N1—Ni—N2—C10176.50 (18)C19—C20—C21—C220.4 (4)
N4—Ni—N2—C1010.28 (18)C23—N4—C22—C211.2 (3)
N3—Ni—N2—C1090.02 (18)Ni—N4—C22—C21172.95 (16)
O9—Ni—N2—C1194.28 (13)C20—C21—C22—N41.0 (3)
N1—Ni—N2—C112.18 (12)C22—N4—C23—C190.0 (3)
N4—Ni—N2—C11171.04 (13)Ni—N4—C23—C19174.89 (14)
N3—Ni—N2—C1191.30 (13)C22—N4—C23—C24179.60 (16)
O1—Ni—N3—C1384.19 (16)Ni—N4—C23—C244.67 (19)
N1—Ni—N3—C139.47 (16)C20—C19—C23—N41.2 (3)
N4—Ni—N3—C13178.18 (17)C18—C19—C23—N4179.07 (17)
N2—Ni—N3—C1389.60 (16)C20—C19—C23—C24178.33 (17)
O1—Ni—N3—C2495.81 (12)C18—C19—C23—C241.4 (3)
N1—Ni—N3—C24170.53 (11)C13—N3—C24—C160.6 (2)
N4—Ni—N3—C241.82 (11)Ni—N3—C24—C16179.43 (13)
N2—Ni—N3—C2490.40 (12)C13—N3—C24—C23179.96 (15)
O9—Ni—N4—C228.27 (17)Ni—N3—C24—C230.04 (18)
O1—Ni—N4—C2297.51 (17)C15—C16—C24—N31.4 (3)
N2—Ni—N4—C2283.78 (17)C17—C16—C24—N3176.94 (17)
N3—Ni—N4—C22177.86 (17)C15—C16—C24—C23179.25 (17)
O9—Ni—N4—C23177.36 (12)C17—C16—C24—C232.4 (3)
O1—Ni—N4—C2388.13 (12)N4—C23—C24—N33.2 (2)
N2—Ni—N4—C2390.59 (13)C19—C23—C24—N3176.39 (15)
N3—Ni—N4—C233.49 (11)N4—C23—C24—C16177.41 (15)
C12—N1—C1—C20.2 (3)C19—C23—C24—C163.0 (3)
Ni—N1—C1—C2178.76 (16)Ni—O1—C25—O23.4 (3)
N1—C1—C2—C31.0 (3)Ni—O1—C25—C26177.12 (11)
C1—C2—C3—C40.7 (4)O2—C25—C26—C27178.97 (17)
C2—C3—C4—C120.4 (3)O1—C25—C26—C271.5 (2)
C2—C3—C4—C5179.3 (2)O2—C25—C26—C310.5 (3)
C12—C4—C5—C62.5 (4)O1—C25—C26—C31178.98 (17)
C3—C4—C5—C6177.8 (2)C31—C26—C27—O3178.65 (17)
C4—C5—C6—C70.0 (4)C25—C26—C27—O31.8 (3)
C5—C6—C7—C8176.5 (2)C31—C26—C27—C280.5 (3)
C5—C6—C7—C112.4 (4)C25—C26—C27—C28179.04 (17)
C11—C7—C8—C90.6 (3)O3—C27—C28—C29178.93 (18)
C6—C7—C8—C9179.5 (2)C26—C27—C28—C290.2 (3)
C7—C8—C9—C100.1 (4)C27—C28—C29—O4179.65 (18)
C11—N2—C10—C91.1 (3)C27—C28—C29—C300.3 (3)
Ni—N2—C10—C9179.71 (16)O4—C29—C30—C31179.4 (2)
C8—C9—C10—N20.1 (3)C28—C29—C30—C310.6 (3)
C10—N2—C11—C71.9 (3)C29—C30—C31—C260.3 (3)
Ni—N2—C11—C7179.27 (15)C27—C26—C31—C300.2 (3)
C10—N2—C11—C12176.61 (17)C25—C26—C31—C30179.31 (18)
Ni—N2—C11—C122.2 (2)O5—C32—C33—C382.1 (3)
C8—C7—C11—N21.6 (3)O6—C32—C33—C38179.1 (2)
C6—C7—C11—N2179.43 (19)O5—C32—C33—C34176.5 (2)
C8—C7—C11—C12176.82 (19)O6—C32—C33—C340.5 (3)
C6—C7—C11—C122.1 (3)C38—C33—C34—O7180.0 (2)
C1—N1—C12—C41.0 (3)C32—C33—C34—O71.3 (3)
Ni—N1—C12—C4179.95 (15)C38—C33—C34—C351.6 (3)
C1—N1—C12—C11177.89 (18)C32—C33—C34—C35177.1 (2)
Ni—N1—C12—C111.2 (2)O7—C34—C35—C36179.8 (2)
C3—C4—C12—N11.2 (3)C33—C34—C35—C361.7 (3)
C5—C4—C12—N1178.49 (19)C34—C35—C36—O8177.2 (2)
C3—C4—C12—C11177.60 (18)C34—C35—C36—C371.4 (4)
C5—C4—C12—C112.7 (3)O8—C36—C37—C38177.6 (2)
N2—C11—C12—N10.7 (3)C35—C36—C37—C380.9 (4)
C7—C11—C12—N1179.27 (17)C36—C37—C38—C330.8 (4)
N2—C11—C12—C4178.14 (17)C34—C33—C38—C371.1 (3)
C7—C11—C12—C40.4 (3)C32—C33—C38—C37177.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O60.991.772.715 (3)159
O1W—H1B···O5i0.911.782.685 (3)172
O3—H3···O10.991.582.517 (2)157
O4—H4···O1Wii0.921.682.589 (3)172
O7—H7···O60.961.622.508 (3)151
O8—H8···O20.941.872.733 (3)151
O9—H9A···O20.971.722.632 (3)155
O9—H9B···O5iii0.961.662.611 (3)167
C20—H20···O3iv0.932.593.509 (4)168
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y, z+1; (iii) x+1, y+1, z+2; (iv) x, y+1, z+1.
 

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