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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1480–m1481.
Published online 2008 October 31. doi:  10.1107/S1600536808034806
PMCID: PMC2959726

Aqua­(2,2′-bipyrid­yl)(pyrazine-2,6-dicarboxyl­ato)nickel(II) 1.25-hydrate

Abstract

The asymmetric unit of the title compound, [Ni(C6H2N2O4)(C10H8N2)(H2O)]·1.25H2O, contains two independent chemically identical NiII complex cations and two and a half solvent water mol­ecules. The NiII ions are in slightly distorted coordination environments. In the crystal structure, inter­molecular O—H(...)O and weak C—H(...)O hydrogen bonds link cations and water mol­ecules into a three-dimensional network. One of the three uncoordinated water molecules is half-occupied.

Related literature

For related structures, see: Wang et al. (2006 [triangle]); Wang, Weng, et al. (2007 [triangle]); Wang, Zheng & Jin (2007 [triangle]); Wang, Zheng, et al. (2007 [triangle] [triangle], 2008 [triangle]); Wang, Mu et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1480-scheme1.jpg

Experimental

Crystal data

  • [Ni(C6H2N2O4)(C10H8N2)(H2O)]·1.25H2O
  • M r = 421.5
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1480-efi1.jpg
  • a = 10.7616 (12) Å
  • b = 14.8677 (17) Å
  • c = 21.933 (2) Å
  • β = 101.015 (2)°
  • V = 3444.6 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.17 mm−1
  • T = 294 (2) K
  • 0.22 × 0.10 × 0.08 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.796, T max = 0.871
  • 19122 measured reflections
  • 7030 independent reflections
  • 4740 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.102
  • S = 1.04
  • 7030 reflections
  • 496 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.26 e Å−3

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034806/lh2711sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034806/lh2711Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Tianjin Polytechnic University for financial support.

supplementary crystallographic information

Comment

In general, bridging multifunctional organic ligands with N– and O-donors have been proven to be good candidates as versatile coordination sites and as hydrogen-bond acceptors and donors. Pyrazine-2,6-dicarboxylic acid (H2PZDC) has two carboxylic groups and two pyrazine nitrogen atoms, and can be used as hydrogen-bond acceptor as well as hydrogen-bond donor, which assists in the generation of supramolecular structures. Because of the structural character, we have used this ligand in our previous work to construct 3d, 4f and 3d-4f complexes (Wang et al., 2006; Wang, Weng, et al., 2007; Wang, Zheng & Jin, 2007; Wang, Zheng, et al., 2007; Wang, Zheng et al., 2008; Wang, Mu et al., 2008). Generally, when coordinated to transition metal ions, PZDC adopts tridentate (ONO) mode and is involved in various hydrogen-bonding interactions. In a continuation of our work, we report synthesis and structure of the title complex.

The asymmetric unit of the title compound is shown in Fig. 1. In the crystal structure, intermolecular O-H···O (Fig. 2) and weak C-H···O hydrogen bonds link cations and water molecules into a three-dimensional network.

Experimental

A mixture of H2PZDC (0.0204 g, 0.1 mmol), Ni(OAc)2.4H2O(0.0249 g, 0.1 mmol), 2,2'-bipyridine (0.0156 g, 0.1 mmol), deionized water (5 ml) and isopropyl alcohol (1 ml) was sealed in a Teflon-lined stainless steel vessel (23 ml) and heated at 413K for 4 days under autogenous pressure and then cooled slowly to room temperature. The solution was filtered and allowed to stand for four weeks at room temperature. Green crystals were obtained. Anal. calcd. for C32H29Ni2N8O12.5: C, 46.07; H, 3.38; N, 13.44. Found: C, 45.90; H, 3.49; N, 13.27%. IR (KBr pellet, cm-1): 3446br, 1663vs, 1630vs, 1475m, 1446 s, 1393m, 1339m, 1313w, 1192m, 1067m, 1024w, 791w, 766m, 749m.

Refinement

All water H atoms were found in difference Fourier maps and were fixed during refinement at O–H distances of 0.85-0.86 Å, with Uiso(H)=1.2 Ueq(O). The H atoms of C–H and N–H groups were treated as riding, with C–H = 0.93 Å and N–H = 0.86 Å and Uiso (H) = 1.2 Ueq(C,N).

Figures

Fig. 1.
The asymmetric unit of the title complex. Dispacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Part of the crystal structure of the title compound. Dashed lines indicate the donor-acceptor separation of O-H···O hydrogen bonds. The solvent water molecules are not shown.

Crystal data

[Ni(C6H2N2O4)(C10H8N2)(H2O)]·1.25H2OF(000) = 1732
Mr = 421.5Dx = 1.626 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5479 reflections
a = 10.7616 (12) Åθ = 2.4–26.1°
b = 14.8677 (17) ŵ = 1.17 mm1
c = 21.933 (2) ÅT = 294 K
β = 101.015 (2)°Block, green
V = 3444.6 (7) Å30.22 × 0.1 × 0.08 mm
Z = 8

Data collection

Bruker SMART CCD diffractometer7030 independent reflections
Radiation source: fine-focus sealed tube4740 reflections with I > 2σ(I)
graphiteRint = 0.035
[var phi] and ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→13
Tmin = 0.796, Tmax = 0.871k = −15→18
19122 measured reflectionsl = −27→27

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.042P)2 + 1.0664P] where P = (Fo2 + 2Fc2)/3
7030 reflections(Δ/σ)max < 0.001
496 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Ni10.49882 (4)0.13832 (3)0.158117 (18)0.04624 (12)
Ni20.90485 (4)0.54725 (3)0.148920 (17)0.04493 (12)
O10.69996 (19)0.12922 (15)0.15470 (9)0.0509 (5)
O20.8901 (2)0.17207 (17)0.20621 (11)0.0627 (6)
O30.3425 (2)0.17792 (16)0.19965 (11)0.0613 (6)
O40.2998 (2)0.24476 (17)0.28546 (13)0.0739 (7)
O50.52042 (19)0.01499 (15)0.20153 (10)0.0557 (6)
H5A0.4525−0.00410.21140.067*
H5B0.58690.01280.22920.067*
O61.10272 (19)0.54558 (15)0.15004 (9)0.0504 (5)
O71.2852 (2)0.49209 (17)0.20287 (10)0.0633 (6)
O80.73667 (19)0.51540 (15)0.18615 (10)0.0556 (5)
O90.6790 (2)0.44246 (16)0.26578 (12)0.0682 (7)
O100.91729 (19)0.66902 (14)0.19526 (9)0.0529 (5)
H10A0.97880.66850.22630.063*
H10B0.84660.68730.20310.063*
N10.5827 (2)0.20244 (16)0.23439 (11)0.0444 (6)
N20.6981 (3)0.26952 (19)0.34744 (12)0.0604 (7)
N30.4080 (3)0.07653 (18)0.07857 (12)0.0550 (7)
N40.4885 (2)0.24284 (18)0.09517 (12)0.0519 (6)
N50.9733 (2)0.48052 (16)0.22650 (11)0.0442 (6)
N61.0718 (3)0.4020 (2)0.33821 (12)0.0604 (7)
N70.8681 (2)0.43822 (17)0.08934 (11)0.0461 (6)
N80.8626 (2)0.61198 (18)0.06530 (11)0.0489 (6)
C10.7726 (3)0.1651 (2)0.19953 (14)0.0473 (7)
C20.7088 (3)0.2040 (2)0.24956 (13)0.0438 (7)
C30.7649 (3)0.2362 (2)0.30740 (14)0.0534 (8)
H30.85270.23450.31880.064*
C40.5734 (4)0.2687 (2)0.32989 (16)0.0594 (9)
H40.52440.29300.35640.071*
C50.5125 (3)0.2329 (2)0.27347 (14)0.0496 (7)
C60.3719 (3)0.2181 (2)0.25151 (18)0.0577 (8)
C70.3595 (4)−0.0066 (3)0.07472 (19)0.0750 (11)
H70.3617−0.03960.11100.090*
C80.3065 (4)−0.0447 (3)0.0188 (2)0.0921 (14)
H80.2738−0.10270.01730.111*
C90.3022 (4)0.0034 (3)−0.0349 (2)0.0946 (15)
H90.2684−0.0219−0.07330.114*
C100.3488 (4)0.0897 (3)−0.03107 (17)0.0792 (12)
H100.34490.1240−0.06680.095*
C110.4016 (3)0.1253 (2)0.02637 (15)0.0570 (8)
C120.4508 (3)0.2175 (2)0.03524 (14)0.0534 (8)
C130.4574 (3)0.2769 (3)−0.01248 (17)0.0683 (10)
H130.43130.2588−0.05350.082*
C140.5023 (4)0.3625 (3)0.00065 (19)0.0726 (11)
H140.50830.4025−0.03130.087*
C150.5384 (4)0.3881 (3)0.06166 (19)0.0695 (10)
H150.56750.44610.07180.083*
C160.5307 (3)0.3264 (2)0.10734 (17)0.0586 (8)
H160.55600.34370.14860.070*
C171.1696 (3)0.5046 (2)0.19481 (14)0.0476 (7)
C181.0976 (3)0.4675 (2)0.24250 (13)0.0453 (7)
C191.1455 (3)0.4261 (2)0.29852 (15)0.0552 (8)
H191.23190.41460.30890.066*
C200.9481 (3)0.4179 (2)0.32100 (15)0.0548 (8)
H200.89470.40320.34820.066*
C210.8961 (3)0.4554 (2)0.26393 (14)0.0461 (7)
C220.7577 (3)0.4730 (2)0.23687 (16)0.0504 (7)
C230.8701 (3)0.3514 (2)0.10518 (15)0.0541 (8)
H230.88930.33650.14710.065*
C240.8451 (3)0.2828 (2)0.06233 (16)0.0604 (9)
H240.84680.22300.07480.072*
C250.8175 (3)0.3058 (2)0.00035 (15)0.0626 (9)
H250.80080.2611−0.02980.075*
C260.8147 (3)0.3947 (2)−0.01701 (15)0.0574 (8)
H260.79630.4106−0.05880.069*
C270.8394 (3)0.4604 (2)0.02840 (14)0.0468 (7)
C280.8390 (3)0.5577 (2)0.01516 (13)0.0469 (7)
C290.8194 (3)0.5928 (3)−0.04470 (15)0.0605 (9)
H290.79970.5548−0.07880.073*
C300.8294 (3)0.6840 (3)−0.05311 (18)0.0685 (10)
H300.81590.7084−0.09290.082*
C310.8596 (3)0.7385 (3)−0.00193 (18)0.0658 (10)
H310.87120.7999−0.00660.079*
C320.8723 (3)0.7013 (2)0.05624 (17)0.0585 (8)
H320.88820.73910.09070.070*
O110.4752 (3)0.56707 (19)0.13832 (11)0.0797 (8)
H11A0.41920.54450.15630.096*
H11B0.55140.55040.15140.096*
O120.0915 (3)0.1333 (3)0.13827 (16)0.1178 (12)
H12A0.15990.10440.15050.141*
H12B0.06220.11140.10260.141*
O130.0028 (10)0.0642 (8)0.0279 (6)0.235 (6)0.50
H13A0.03500.01140.03310.282*0.50
H13B−0.07760.06270.02040.282*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0410 (2)0.0513 (2)0.0450 (2)−0.00191 (17)0.00470 (16)−0.00111 (18)
Ni20.0391 (2)0.0523 (2)0.0422 (2)0.00067 (17)0.00479 (16)−0.00043 (17)
O10.0459 (12)0.0617 (14)0.0452 (12)−0.0003 (10)0.0094 (10)−0.0043 (10)
O20.0385 (13)0.0865 (18)0.0628 (14)0.0001 (11)0.0086 (10)0.0134 (13)
O30.0426 (13)0.0677 (15)0.0741 (15)−0.0030 (11)0.0123 (11)−0.0088 (13)
O40.0611 (16)0.0648 (16)0.107 (2)−0.0064 (12)0.0438 (15)−0.0133 (14)
O50.0431 (12)0.0632 (14)0.0592 (13)−0.0063 (10)0.0061 (10)0.0097 (11)
O60.0427 (12)0.0635 (14)0.0451 (11)−0.0007 (10)0.0092 (9)0.0010 (10)
O70.0386 (13)0.0897 (18)0.0612 (14)0.0015 (11)0.0083 (10)−0.0070 (13)
O80.0385 (12)0.0664 (15)0.0613 (14)0.0016 (10)0.0080 (10)0.0019 (12)
O90.0531 (14)0.0663 (16)0.0934 (18)0.0054 (11)0.0350 (13)0.0159 (13)
O100.0423 (12)0.0601 (14)0.0552 (12)0.0041 (10)0.0068 (10)−0.0087 (10)
N10.0453 (15)0.0449 (14)0.0445 (13)−0.0043 (11)0.0122 (11)0.0010 (11)
N20.074 (2)0.0609 (18)0.0449 (15)−0.0132 (15)0.0083 (14)−0.0022 (13)
N30.0522 (16)0.0561 (17)0.0530 (16)−0.0020 (13)0.0004 (13)−0.0071 (13)
N40.0491 (16)0.0555 (17)0.0501 (15)0.0030 (12)0.0071 (12)0.0026 (12)
N50.0416 (14)0.0484 (14)0.0424 (13)0.0000 (11)0.0076 (11)−0.0035 (11)
N60.065 (2)0.0651 (19)0.0488 (16)0.0026 (14)0.0050 (14)0.0079 (14)
N70.0460 (14)0.0533 (16)0.0387 (13)−0.0002 (11)0.0072 (11)0.0014 (11)
N80.0426 (14)0.0539 (16)0.0496 (15)0.0022 (11)0.0075 (12)0.0024 (12)
C10.0461 (18)0.0491 (18)0.0470 (17)0.0026 (14)0.0095 (14)0.0101 (14)
C20.0421 (17)0.0447 (17)0.0431 (16)−0.0061 (13)0.0046 (13)0.0048 (13)
C30.057 (2)0.0506 (19)0.0494 (18)−0.0080 (15)0.0019 (15)0.0025 (15)
C40.075 (3)0.056 (2)0.0527 (19)−0.0087 (17)0.0256 (18)−0.0061 (16)
C50.054 (2)0.0450 (17)0.0525 (18)−0.0047 (14)0.0179 (15)0.0016 (14)
C60.053 (2)0.0485 (19)0.076 (2)−0.0003 (15)0.0251 (18)−0.0009 (17)
C70.076 (3)0.065 (2)0.076 (3)−0.006 (2)−0.006 (2)−0.009 (2)
C80.100 (4)0.066 (3)0.096 (3)−0.008 (2)−0.017 (3)−0.022 (3)
C90.104 (4)0.096 (4)0.072 (3)0.008 (3)−0.015 (2)−0.036 (3)
C100.089 (3)0.089 (3)0.054 (2)0.007 (2)−0.001 (2)−0.013 (2)
C110.0487 (19)0.071 (2)0.0497 (18)0.0073 (16)0.0052 (15)−0.0071 (17)
C120.0469 (18)0.067 (2)0.0462 (17)0.0096 (15)0.0087 (14)0.0018 (16)
C130.066 (2)0.087 (3)0.053 (2)0.014 (2)0.0145 (18)0.0071 (19)
C140.071 (3)0.075 (3)0.076 (3)0.011 (2)0.024 (2)0.025 (2)
C150.072 (3)0.056 (2)0.084 (3)0.0040 (18)0.021 (2)0.011 (2)
C160.059 (2)0.052 (2)0.062 (2)0.0026 (16)0.0076 (17)0.0027 (17)
C170.0385 (17)0.0571 (19)0.0473 (17)−0.0020 (14)0.0083 (13)−0.0120 (15)
C180.0406 (17)0.0494 (18)0.0448 (16)0.0029 (13)0.0050 (13)−0.0072 (13)
C190.0495 (19)0.060 (2)0.0525 (19)0.0075 (15)0.0003 (15)−0.0005 (16)
C200.060 (2)0.057 (2)0.0487 (18)−0.0043 (16)0.0140 (16)0.0001 (15)
C210.0472 (17)0.0454 (17)0.0465 (16)0.0006 (14)0.0109 (14)−0.0052 (14)
C220.0450 (18)0.0493 (19)0.0585 (19)0.0033 (14)0.0144 (15)−0.0025 (15)
C230.058 (2)0.057 (2)0.0465 (17)−0.0006 (16)0.0093 (15)0.0054 (15)
C240.064 (2)0.055 (2)0.062 (2)−0.0036 (16)0.0100 (17)−0.0016 (17)
C250.076 (2)0.062 (2)0.0496 (19)−0.0089 (18)0.0109 (17)−0.0112 (16)
C260.059 (2)0.070 (2)0.0437 (17)−0.0057 (17)0.0100 (15)−0.0025 (16)
C270.0369 (16)0.0585 (19)0.0451 (16)−0.0010 (13)0.0085 (13)−0.0002 (14)
C280.0374 (16)0.061 (2)0.0433 (16)0.0036 (14)0.0095 (13)0.0022 (14)
C290.067 (2)0.071 (2)0.0465 (18)0.0098 (18)0.0168 (16)0.0062 (16)
C300.069 (2)0.076 (3)0.064 (2)0.014 (2)0.0234 (19)0.021 (2)
C310.061 (2)0.057 (2)0.080 (3)0.0065 (17)0.0164 (19)0.018 (2)
C320.052 (2)0.054 (2)0.067 (2)0.0039 (15)0.0062 (16)0.0003 (17)
O110.0726 (18)0.099 (2)0.0685 (16)0.0126 (15)0.0163 (13)0.0101 (15)
O120.087 (2)0.157 (3)0.106 (2)0.005 (2)0.0110 (19)0.023 (2)
O130.156 (9)0.262 (15)0.298 (16)−0.084 (9)0.074 (10)−0.068 (12)

Geometric parameters (Å, °)

Ni1—N11.986 (2)C7—C81.373 (5)
Ni1—N32.047 (3)C7—H70.9300
Ni1—O52.059 (2)C8—C91.371 (6)
Ni1—N42.067 (3)C8—H80.9300
Ni1—O32.143 (2)C9—C101.374 (6)
Ni1—O12.184 (2)C9—H90.9300
Ni2—N51.986 (2)C10—C111.384 (5)
Ni2—N82.044 (2)C10—H100.9300
Ni2—O102.068 (2)C11—C121.470 (5)
Ni2—N72.072 (2)C12—C131.381 (5)
Ni2—O62.125 (2)C13—C141.373 (5)
Ni2—O82.175 (2)C13—H130.9300
O1—C11.253 (4)C14—C151.374 (5)
O2—C11.249 (4)C14—H140.9300
O3—C61.270 (4)C15—C161.372 (5)
O4—C61.238 (4)C15—H150.9300
O5—H5A0.8500C16—H160.9300
O5—H5B0.8460C17—C181.519 (4)
O6—C171.258 (4)C18—C191.383 (4)
O7—C171.237 (3)C19—H190.9300
O8—C221.261 (4)C20—C211.387 (4)
O9—C221.237 (4)C20—H200.9300
O10—H10A0.8543C21—C221.517 (4)
O10—H10B0.8555C23—C241.377 (4)
N1—C51.326 (4)C23—H230.9300
N1—C21.334 (4)C24—C251.378 (5)
N2—C41.324 (4)C24—H240.9300
N2—C31.332 (4)C25—C261.375 (5)
N3—C71.339 (4)C25—H250.9300
N3—C111.346 (4)C26—C271.384 (4)
N4—C161.332 (4)C26—H260.9300
N4—C121.353 (4)C27—C281.475 (4)
N5—C211.328 (4)C28—C291.391 (4)
N5—C181.331 (4)C29—C301.376 (5)
N6—C201.334 (4)C29—H290.9300
N6—C191.334 (4)C30—C311.372 (5)
N7—C231.337 (4)C30—H300.9300
N7—C271.354 (4)C31—C321.373 (5)
N8—C281.348 (4)C31—H310.9300
N8—C321.350 (4)C32—H320.9300
C1—C21.515 (4)O11—H11A0.8487
C2—C31.382 (4)O11—H11B0.8527
C3—H30.9300O12—H12A0.8501
C4—C51.390 (4)O12—H12B0.8505
C4—H40.9300O13—H13A0.8562
C5—C61.514 (5)O13—H13B0.8500
N1—Ni1—N3177.78 (11)C8—C7—H7119.1
N1—Ni1—O592.57 (9)C9—C8—C7119.6 (4)
N3—Ni1—O589.30 (10)C9—C8—H8120.2
N1—Ni1—N499.17 (10)C7—C8—H8120.2
N3—Ni1—N479.18 (11)C8—C9—C10118.8 (4)
O5—Ni1—N4164.84 (10)C8—C9—H9120.6
N1—Ni1—O377.15 (9)C10—C9—H9120.6
N3—Ni1—O3101.53 (10)C9—C10—C11119.6 (4)
O5—Ni1—O394.39 (9)C9—C10—H10120.2
N4—Ni1—O397.53 (10)C11—C10—H10120.2
N1—Ni1—O176.38 (9)N3—C11—C10120.9 (4)
N3—Ni1—O1104.94 (9)N3—C11—C12115.6 (3)
O5—Ni1—O186.31 (8)C10—C11—C12123.5 (3)
N4—Ni1—O187.17 (9)N4—C12—C13120.6 (3)
O3—Ni1—O1153.53 (8)N4—C12—C11115.0 (3)
N5—Ni2—N8170.60 (10)C13—C12—C11124.4 (3)
N5—Ni2—O1092.16 (9)C14—C13—C12120.0 (4)
N8—Ni2—O1090.64 (9)C14—C13—H13120.0
N5—Ni2—N798.30 (10)C12—C13—H13120.0
N8—Ni2—N779.60 (10)C13—C14—C15119.0 (4)
O10—Ni2—N7168.92 (9)C13—C14—H14120.5
N5—Ni2—O677.14 (9)C15—C14—H14120.5
N8—Ni2—O693.80 (9)C16—C15—C14118.7 (4)
O10—Ni2—O691.94 (8)C16—C15—H15120.6
N7—Ni2—O693.92 (9)C14—C15—H15120.6
N5—Ni2—O876.62 (9)N4—C16—C15122.9 (3)
N8—Ni2—O8112.40 (9)N4—C16—H16118.6
O10—Ni2—O889.23 (8)C15—C16—H16118.6
N7—Ni2—O889.66 (9)O7—C17—O6126.4 (3)
O6—Ni2—O8153.76 (8)O7—C17—C18118.6 (3)
C1—O1—Ni1114.87 (19)O6—C17—C18115.0 (3)
C6—O3—Ni1115.4 (2)N5—C18—C19119.0 (3)
Ni1—O5—H5A112.9N5—C18—C17112.6 (3)
Ni1—O5—H5B111.8C19—C18—C17128.4 (3)
H5A—O5—H5B117.0N6—C19—C18122.2 (3)
C17—O6—Ni2115.92 (19)N6—C19—H19118.9
C22—O8—Ni2114.71 (19)C18—C19—H19118.9
Ni2—O10—H10A110.5N6—C20—C21122.3 (3)
Ni2—O10—H10B113.6N6—C20—H20118.8
H10A—O10—H10B115.2C21—C20—H20118.8
C5—N1—C2120.7 (3)N5—C21—C20118.6 (3)
C5—N1—Ni1119.0 (2)N5—C21—C22113.1 (3)
C2—N1—Ni1119.7 (2)C20—C21—C22128.2 (3)
C4—N2—C3116.7 (3)O9—C22—O8127.6 (3)
C7—N3—C11119.2 (3)O9—C22—C21116.9 (3)
C7—N3—Ni1125.8 (3)O8—C22—C21115.4 (3)
C11—N3—Ni1115.0 (2)N7—C23—C24123.1 (3)
C16—N4—C12118.8 (3)N7—C23—H23118.4
C16—N4—Ni1126.5 (2)C24—C23—H23118.4
C12—N4—Ni1114.0 (2)C23—C24—C25117.8 (3)
C21—N5—C18120.8 (3)C23—C24—H24121.1
C21—N5—Ni2119.8 (2)C25—C24—H24121.1
C18—N5—Ni2119.2 (2)C26—C25—C24120.1 (3)
C20—N6—C19117.0 (3)C26—C25—H25120.0
C23—N7—C27118.8 (3)C24—C25—H25120.0
C23—N7—Ni2126.9 (2)C25—C26—C27119.2 (3)
C27—N7—Ni2114.3 (2)C25—C26—H26120.4
C28—N8—C32118.5 (3)C27—C26—H26120.4
C28—N8—Ni2115.2 (2)N7—C27—C26121.0 (3)
C32—N8—Ni2125.8 (2)N7—C27—C28115.1 (3)
O2—C1—O1126.4 (3)C26—C27—C28123.9 (3)
O2—C1—C2118.2 (3)N8—C28—C29121.1 (3)
O1—C1—C2115.4 (3)N8—C28—C27115.7 (3)
N1—C2—C3118.7 (3)C29—C28—C27123.2 (3)
N1—C2—C1113.1 (2)C30—C29—C28119.6 (3)
C3—C2—C1128.2 (3)C30—C29—H29120.2
N2—C3—C2122.6 (3)C28—C29—H29120.2
N2—C3—H3118.7C31—C30—C29119.0 (3)
C2—C3—H3118.7C31—C30—H30120.5
N2—C4—C5122.8 (3)C29—C30—H30120.5
N2—C4—H4118.6C30—C31—C32119.2 (3)
C5—C4—H4118.6C30—C31—H31120.4
N1—C5—C4118.4 (3)C32—C31—H31120.4
N1—C5—C6113.8 (3)N8—C32—C31122.4 (3)
C4—C5—C6127.6 (3)N8—C32—H32118.8
O4—C6—O3127.7 (3)C31—C32—H32118.8
O4—C6—C5117.7 (3)H11A—O11—H11B116.8
O3—C6—C5114.6 (3)H12A—O12—H12B104.0
N3—C7—C8121.8 (4)H13A—O13—H13B111.9
N3—C7—H7119.1
N1—Ni1—O1—C10.7 (2)C2—N1—C5—C6−174.5 (3)
N3—Ni1—O1—C1178.8 (2)Ni1—N1—C5—C6−3.3 (3)
O5—Ni1—O1—C1−92.9 (2)N2—C4—C5—N1−3.4 (5)
N4—Ni1—O1—C1100.8 (2)N2—C4—C5—C6172.2 (3)
O3—Ni1—O1—C1−0.4 (3)Ni1—O3—C6—O4−177.4 (3)
N1—Ni1—O3—C6−2.6 (2)Ni1—O3—C6—C51.7 (4)
N3—Ni1—O3—C6179.2 (2)N1—C5—C6—O4−180.0 (3)
O5—Ni1—O3—C689.0 (2)C4—C5—C6—O44.2 (5)
N4—Ni1—O3—C6−100.3 (2)N1—C5—C6—O30.9 (4)
O1—Ni1—O3—C6−1.5 (4)C4—C5—C6—O3−174.9 (3)
N5—Ni2—O6—C171.5 (2)C11—N3—C7—C81.9 (6)
N8—Ni2—O6—C17−175.9 (2)Ni1—N3—C7—C8−176.1 (3)
O10—Ni2—O6—C1793.3 (2)N3—C7—C8—C9−0.3 (7)
N7—Ni2—O6—C17−96.1 (2)C7—C8—C9—C10−1.4 (7)
O8—Ni2—O6—C171.1 (3)C8—C9—C10—C111.6 (7)
N5—Ni2—O8—C220.8 (2)C7—N3—C11—C10−1.8 (5)
N8—Ni2—O8—C22178.0 (2)Ni1—N3—C11—C10176.5 (3)
O10—Ni2—O8—C22−91.6 (2)C7—N3—C11—C12176.8 (3)
N7—Ni2—O8—C2299.4 (2)Ni1—N3—C11—C12−5.0 (4)
O6—Ni2—O8—C221.2 (3)C9—C10—C11—N30.0 (6)
O5—Ni1—N1—C5−90.7 (2)C9—C10—C11—C12−178.4 (4)
N4—Ni1—N1—C598.9 (2)C16—N4—C12—C130.8 (5)
O3—Ni1—N1—C53.2 (2)Ni1—N4—C12—C13−170.4 (2)
O1—Ni1—N1—C5−176.3 (2)C16—N4—C12—C11−177.9 (3)
O5—Ni1—N1—C280.6 (2)Ni1—N4—C12—C1110.9 (3)
N4—Ni1—N1—C2−89.8 (2)N3—C11—C12—N4−4.1 (4)
O3—Ni1—N1—C2174.5 (2)C10—C11—C12—N4174.4 (3)
O1—Ni1—N1—C2−5.0 (2)N3—C11—C12—C13177.3 (3)
O5—Ni1—N3—C716.3 (3)C10—C11—C12—C13−4.2 (5)
N4—Ni1—N3—C7−173.6 (3)N4—C12—C13—C140.0 (5)
O3—Ni1—N3—C7−78.0 (3)C11—C12—C13—C14178.5 (3)
O1—Ni1—N3—C7102.3 (3)C12—C13—C14—C15−1.1 (6)
O5—Ni1—N3—C11−161.8 (2)C13—C14—C15—C161.4 (6)
N4—Ni1—N3—C118.3 (2)C12—N4—C16—C15−0.4 (5)
O3—Ni1—N3—C11103.9 (2)Ni1—N4—C16—C15169.5 (3)
O1—Ni1—N3—C11−75.8 (2)C14—C15—C16—N4−0.7 (6)
N1—Ni1—N4—C160.7 (3)Ni2—O6—C17—O7176.5 (3)
N3—Ni1—N4—C16179.2 (3)Ni2—O6—C17—C18−3.2 (3)
O5—Ni1—N4—C16−139.6 (3)C21—N5—C18—C190.9 (4)
O3—Ni1—N4—C1678.8 (3)Ni2—N5—C18—C19175.9 (2)
O1—Ni1—N4—C16−75.0 (3)C21—N5—C18—C17−177.4 (3)
N1—Ni1—N4—C12171.0 (2)Ni2—N5—C18—C17−2.5 (3)
N3—Ni1—N4—C12−10.5 (2)O7—C17—C18—N5−176.0 (3)
O5—Ni1—N4—C1230.7 (5)O6—C17—C18—N53.7 (4)
O3—Ni1—N4—C12−110.8 (2)O7—C17—C18—C195.8 (5)
O1—Ni1—N4—C1295.3 (2)O6—C17—C18—C19−174.5 (3)
O10—Ni2—N5—C2184.3 (2)C20—N6—C19—C181.4 (5)
N7—Ni2—N5—C21−92.1 (2)N5—C18—C19—N6−2.8 (5)
O6—Ni2—N5—C21175.8 (2)C17—C18—C19—N6175.3 (3)
O8—Ni2—N5—C21−4.4 (2)C19—N6—C20—C211.7 (5)
O10—Ni2—N5—C18−90.8 (2)C18—N5—C21—C202.1 (4)
N7—Ni2—N5—C1892.9 (2)Ni2—N5—C21—C20−172.9 (2)
O6—Ni2—N5—C180.7 (2)C18—N5—C21—C22−178.2 (3)
O8—Ni2—N5—C18−179.5 (2)Ni2—N5—C21—C226.9 (3)
N5—Ni2—N7—C2310.9 (3)N6—C20—C21—N5−3.5 (5)
N8—Ni2—N7—C23−178.4 (3)N6—C20—C21—C22176.8 (3)
O10—Ni2—N7—C23−149.8 (4)Ni2—O8—C22—O9−175.5 (3)
O6—Ni2—N7—C2388.4 (3)Ni2—O8—C22—C212.4 (3)
O8—Ni2—N7—C23−65.5 (3)N5—C21—C22—O9172.2 (3)
N5—Ni2—N7—C27−169.2 (2)C20—C21—C22—O9−8.1 (5)
N8—Ni2—N7—C271.6 (2)N5—C21—C22—O8−5.9 (4)
O10—Ni2—N7—C2730.2 (6)C20—C21—C22—O8173.9 (3)
O6—Ni2—N7—C27−91.6 (2)C27—N7—C23—C240.5 (5)
O8—Ni2—N7—C27114.4 (2)Ni2—N7—C23—C24−179.6 (2)
O10—Ni2—N8—C28−177.6 (2)N7—C23—C24—C250.3 (5)
N7—Ni2—N8—C28−2.9 (2)C23—C24—C25—C26−0.5 (5)
O6—Ni2—N8—C2890.4 (2)C24—C25—C26—C27−0.2 (5)
O8—Ni2—N8—C28−88.2 (2)C23—N7—C27—C26−1.1 (4)
O10—Ni2—N8—C3211.3 (3)Ni2—N7—C27—C26178.9 (2)
N7—Ni2—N8—C32−174.0 (3)C23—N7—C27—C28179.8 (3)
O6—Ni2—N8—C32−80.7 (3)Ni2—N7—C27—C28−0.1 (3)
O8—Ni2—N8—C32100.7 (3)C25—C26—C27—N71.0 (5)
Ni1—O1—C1—O2−176.4 (2)C25—C26—C27—C28179.9 (3)
Ni1—O1—C1—C23.1 (3)C32—N8—C28—C29−2.8 (4)
C5—N1—C2—C31.3 (4)Ni2—N8—C28—C29−174.6 (2)
Ni1—N1—C2—C3−169.8 (2)C32—N8—C28—C27175.5 (3)
C5—N1—C2—C1179.1 (3)Ni2—N8—C28—C273.6 (3)
Ni1—N1—C2—C17.9 (3)N7—C27—C28—N8−2.3 (4)
O2—C1—C2—N1172.5 (3)C26—C27—C28—N8178.7 (3)
O1—C1—C2—N1−7.0 (4)N7—C27—C28—C29175.9 (3)
O2—C1—C2—C3−10.0 (5)C26—C27—C28—C29−3.1 (5)
O1—C1—C2—C3170.5 (3)N8—C28—C29—C302.7 (5)
C4—N2—C3—C21.5 (5)C27—C28—C29—C30−175.4 (3)
N1—C2—C3—N2−3.1 (5)C28—C29—C30—C310.5 (5)
C1—C2—C3—N2179.5 (3)C29—C30—C31—C32−3.4 (5)
C3—N2—C4—C51.7 (5)C28—N8—C32—C31−0.3 (5)
C2—N1—C5—C41.7 (4)Ni2—N8—C32—C31170.5 (3)
Ni1—N1—C5—C4172.9 (2)C30—C31—C32—N83.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C32—H32···O100.932.483.033 (4)118
C31—H31···O13i0.932.533.384 (11)153
C29—H29···O6ii0.932.533.318 (4)143
C26—H26···O6ii0.932.543.329 (4)143
C14—H14···O11i0.932.433.275 (5)151
C9—H9···O1iii0.932.473.281 (5)146
C7—H7···O50.932.503.000 (4)114
O13—H13A···O13iv0.861.732.26 (2)118
O12—H12B···O130.851.792.636 (12)179
O12—H12A···O30.852.332.856 (4)121
O11—H11B···O80.852.062.912 (3)177
O11—H11A···O7v0.852.072.921 (4)178
O10—H10B···O4vi0.861.852.699 (3)170
O10—H10A···O2vii0.851.842.694 (3)178
O5—H5B···O7viii0.851.852.686 (3)169
O5—H5A···O9ix0.851.782.621 (3)173

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z; (iii) −x+1, −y, −z; (iv) −x, −y, −z; (v) x−1, y, z; (vi) −x+1, y+1/2, −z+1/2; (vii) −x+2, y+1/2, −z+1/2; (viii) −x+2, y−1/2, −z+1/2; (ix) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2711).

References

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