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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m222–m223.
Published online 2007 December 18. doi:  10.1107/S1600536807059053
PMCID: PMC2915148

Tris(ethyl carbazate-κ2 N,O)nickel(II) dinitrate

Abstract

The asymmetric unit of the title compound, [Ni(C3H8N2O2)3](NO3)2, contains two independent cations, each built up around a fac-NiN3O3 octa­hedron, and four nitrate anions. Numerous cation-to-anion N—H(...)O hydrogen bonds, some of which are bifurcated, help to establish the packing.

Related literature

For related structures, see: Lanfredi et al. (1976 [triangle]); Zhang et al. (2005 [triangle]); Srinivasan et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m222-scheme1.jpg

Experimental

Crystal data

  • [Ni(C3H8N2O2)3](NO3)2
  • M r = 495.07
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m222-efi1.jpg
  • a = 14.0580 (8) Å
  • b = 8.6571 (3) Å
  • c = 33.6639 (18) Å
  • β = 92.652 (1)°
  • V = 4092.6 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.02 mm−1
  • T = 293 (2) K
  • 0.36 × 0.29 × 0.17 mm

Data collection

  • Bruker SMART1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2003 [triangle]) T min = 0.710, T max = 0.845
  • 26981 measured reflections
  • 11856 independent reflections
  • 6057 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.125
  • S = 0.94
  • 11856 reflections
  • 547 parameters
  • H-atom parameters constrained
  • Δρmax = 0.42 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: HKL DENZO (Otwinowski & Minor 1997 [triangle]), HKL SCALEPACK and SORTAV (Blessing 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807059053/sg2208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807059053/sg2208Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound, (I), is isostructural with its zinc congener (Zhang et al., 2005). The cobalt-containing compound was also reported to have the same structure by Zhang and co-workers. We have recently observed a supercell for the latter phase (Srinivasan et al., 2007).

The two [Ni(C3H8N2O2)3]2+ complex cations in (I) are similar (Fig. 1) and are each built up around a slightly distorted fac-NiN3O3 octahedral core (Table 1). A five-membered –Ni—N—N—C—O– chelate ring arises for each of the six distinct N,O-bidentate ligands.

The crystal packing for (I) is consolidated by a large number of cation-to-anion N—H···O hydrogen bonds (Table 2), a number of which are bifurcated.

The crysatl structure of the [Ni(C3H8N2O2)3]2+ complex cation accompanied by chloride ions was described some time ago (Lanfredi et al., 1976).

Experimental

Ethyl carbazate (0.208 g, 0.002 mol) was added to an aqueous solution (25 ml) containing formic acid (85%, 0.08 ml). To this solution was added nickel nitrate hexahydrate (0.291 g, 0.001 mol) dissolved in 50 ml of double distilled water. The resulting green solution was concentrated over a water bath to about 15 ml and kept for crystallization at room temperature. Blue blocks of (I) obtained after a week were separated and washed with ethanol and air dried.

Refinement

The diffraction data were carefully examined, but no trace of a supercell was discernable. The hydrogen atoms were geometrically placed (N—H = 0.86–0.90 Å, C—H = 0.96–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(N,C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
View of the Ni2-containing complex cation in (I) shoiwng 50% displacement ellipsoids (arbitrary spheres for the H atoms). The C-bound H atoms are omitted for clarity.

Crystal data

[Ni(C3H8N2O2)3](NO3)2F000 = 2064
Mr = 495.07Dx = 1.607 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6204 reflections
a = 14.0580 (8) Åθ = 4.3–28.0º
b = 8.6571 (3) ŵ = 1.02 mm1
c = 33.6639 (18) ÅT = 293 (2) K
β = 92.652 (1)ºBlock, blue
V = 4092.6 (3) Å30.36 × 0.29 × 0.17 mm
Z = 8

Data collection

Bruker SMART1000 CCD diffractometer11856 independent reflections
Radiation source: fine-focus sealed tube6057 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.042
T = 293(2) Kθmax = 30.2º
ω scansθmin = 4.3º
Absorption correction: multi-scan(SADABS; Bruker, 2003)h = −19→18
Tmin = 0.710, Tmax = 0.845k = −6→12
26981 measured reflectionsl = −47→47

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.125  w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
11856 reflectionsΔρmax = 0.42 e Å3
547 parametersΔρmin = −0.36 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. ? ?
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*/Ueq
Ni10.81839 (3)0.75534 (4)0.154396 (10)0.04181 (10)
C10.9239 (2)1.0247 (4)0.15603 (9)0.0508 (7)
C21.0145 (4)1.1639 (6)0.10942 (15)0.1108 (17)
H2A1.08301.17740.11050.133*
H2B0.99931.07330.09340.133*
C30.9722 (6)1.2897 (8)0.09249 (18)0.159 (3)
H3A0.99891.30940.06730.239*
H3B0.98261.37750.10950.239*
H3C0.90501.27130.08860.239*
N10.82926 (19)0.9099 (3)0.20261 (7)0.0487 (6)
H1A0.77230.95290.20670.058*
H1B0.84920.85990.22490.058*
N20.8955 (2)1.0241 (3)0.19293 (7)0.0552 (7)
H20.91651.09040.21020.066*
O10.90039 (15)0.9274 (2)0.13099 (6)0.0508 (5)
O20.9818 (2)1.1409 (3)0.14981 (8)0.0813 (8)
C40.7404 (2)0.6828 (3)0.07980 (9)0.0511 (7)
C50.7692 (3)0.5000 (5)0.02964 (12)0.0849 (13)
H5A0.72870.43800.01180.102*
H5B0.79080.43530.05180.102*
C60.8520 (5)0.5551 (7)0.00840 (16)0.135 (2)
H6A0.88910.46830.00040.202*
H6B0.89050.62060.02560.202*
H6C0.83040.6124−0.01470.202*
N30.69577 (18)0.8548 (3)0.12911 (7)0.0484 (6)
H3D0.64590.83590.14430.058*
H3E0.70310.95770.12710.058*
N40.6800 (2)0.7887 (3)0.09118 (7)0.0574 (7)
H40.63240.81670.07590.069*
O30.81106 (15)0.6415 (2)0.09979 (6)0.0500 (5)
O40.7153 (2)0.6283 (3)0.04421 (6)0.0738 (7)
C70.9102 (3)0.5165 (4)0.19524 (10)0.0562 (8)
C81.0668 (4)0.4764 (7)0.2236 (2)0.129 (2)
H8A1.06720.58820.22540.155*
H8B1.09010.43410.24890.155*
C91.1191 (6)0.4303 (10)0.1952 (3)0.188 (4)
H9A1.18420.45800.20140.282*
H9B1.09770.47870.17070.282*
H9C1.11400.32020.19250.282*
N50.75100 (18)0.5674 (3)0.17952 (7)0.0500 (6)
H5C0.71050.60030.19760.060*
H5D0.71760.51440.16060.060*
N60.8211 (2)0.4720 (3)0.19776 (8)0.0572 (7)
H60.80650.38870.21000.069*
O50.93445 (15)0.6349 (2)0.17806 (6)0.0535 (5)
O60.9692 (2)0.4191 (3)0.21322 (10)0.0970 (10)
Ni20.36902 (3)0.22636 (4)0.106643 (10)0.04364 (11)
C110.3169 (2)0.0113 (4)0.16235 (9)0.0523 (8)
C120.1854 (3)−0.0161 (6)0.20373 (15)0.1049 (17)
H12A0.19700.07780.21890.126*
H12B0.14190.00810.18140.126*
C130.1443 (4)−0.1278 (6)0.22789 (18)0.130 (2)
H13A0.0887−0.08540.23930.196*
H13B0.1894−0.15780.24870.196*
H13C0.1266−0.21650.21210.196*
N110.45074 (17)0.0358 (3)0.12481 (7)0.0460 (6)
H11A0.4627−0.02410.10380.055*
H11B0.50660.06700.13620.055*
N120.39883 (19)−0.0466 (3)0.15207 (8)0.0565 (7)
H120.4197−0.13260.16190.068*
O110.28303 (15)0.1324 (2)0.14873 (6)0.0532 (5)
O120.27538 (17)−0.0737 (3)0.18905 (8)0.0753 (7)
C140.2889 (2)0.5054 (4)0.12510 (10)0.0546 (8)
C150.1668 (5)0.6550 (7)0.09490 (19)0.150 (3)
H15A0.20000.65350.07030.180*
H15B0.12140.57050.09400.180*
C160.1206 (6)0.7853 (9)0.0973 (2)0.181 (3)
H16A0.07670.79550.07470.272*
H16B0.16490.86970.09770.272*
H16C0.08610.78650.12130.272*
N130.42753 (18)0.3833 (3)0.14845 (7)0.0486 (6)
H13D0.44340.33480.17150.058*
H13E0.48000.42780.13930.058*
N140.35665 (19)0.4951 (3)0.15428 (8)0.0544 (6)
H140.35690.55270.17510.065*
O130.27628 (15)0.4088 (2)0.09905 (6)0.0567 (5)
O140.2364 (2)0.6297 (3)0.12846 (8)0.0846 (8)
C170.3493 (3)0.1147 (3)0.03006 (9)0.0521 (8)
C180.2543 (4)−0.0744 (5)−0.00350 (12)0.0909 (14)
H18A0.2562−0.12510.02220.109*
H18B0.2662−0.1519−0.02350.109*
C190.1596 (4)−0.0083 (7)−0.01148 (19)0.143 (2)
H19A0.1121−0.0859−0.00770.215*
H19B0.15430.0283−0.03840.215*
H19C0.15020.07620.00640.215*
N150.45223 (19)0.2944 (3)0.06042 (7)0.0507 (6)
H15C0.44410.39580.05540.061*
H15D0.51420.27740.06680.061*
N160.4231 (2)0.2065 (3)0.02672 (7)0.0591 (7)
H160.45240.21260.00490.071*
O150.30548 (16)0.0995 (2)0.06056 (6)0.0540 (5)
O160.32763 (19)0.0407 (3)−0.00376 (6)0.0726 (7)
N210.6243 (2)0.1811 (3)0.20952 (7)0.0493 (6)
O210.70396 (17)0.1946 (3)0.22680 (7)0.0665 (6)
O220.60891 (19)0.0714 (3)0.18656 (7)0.0773 (7)
O230.5623 (2)0.2750 (4)0.21627 (8)0.0940 (9)
N310.4518 (2)0.7144 (3)0.05618 (8)0.0550 (6)
O310.49163 (16)0.8417 (2)0.05117 (6)0.0578 (5)
O320.4373 (2)0.6266 (3)0.02821 (8)0.0954 (9)
O330.4328 (3)0.6772 (4)0.08930 (9)0.1372 (15)
N410.6723 (2)0.2646 (3)0.11276 (8)0.0543 (6)
O410.63393 (18)0.1611 (3)0.09159 (7)0.0688 (6)
O420.63042 (17)0.3890 (3)0.11677 (8)0.0743 (7)
O430.7498 (2)0.2417 (3)0.12965 (9)0.0895 (8)
N510.5319 (2)0.6816 (3)0.20948 (8)0.0537 (6)
O510.53746 (17)0.7060 (3)0.17313 (7)0.0660 (6)
O520.60552 (17)0.6768 (3)0.23136 (6)0.0670 (6)
O530.45284 (19)0.6607 (4)0.22271 (9)0.0893 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0468 (2)0.0397 (2)0.03881 (18)0.00573 (16)0.00038 (14)0.00073 (15)
C10.056 (2)0.0479 (18)0.0477 (17)0.0015 (14)−0.0029 (14)0.0069 (14)
C20.157 (5)0.078 (3)0.100 (3)−0.026 (3)0.036 (3)0.015 (3)
C30.215 (8)0.155 (6)0.108 (4)0.041 (5)0.005 (5)0.041 (4)
N10.0639 (17)0.0460 (14)0.0365 (12)0.0081 (12)0.0040 (11)0.0040 (10)
N20.0730 (19)0.0509 (16)0.0413 (14)−0.0059 (13)−0.0011 (13)−0.0037 (11)
O10.0630 (14)0.0492 (12)0.0404 (11)−0.0011 (10)0.0058 (10)0.0006 (9)
O20.104 (2)0.0658 (17)0.0755 (17)−0.0298 (15)0.0178 (15)−0.0017 (13)
C40.068 (2)0.0428 (17)0.0418 (16)0.0023 (15)−0.0059 (15)0.0009 (13)
C50.121 (4)0.062 (3)0.070 (2)0.016 (2)−0.014 (2)−0.0215 (19)
C60.164 (6)0.136 (5)0.108 (4)0.035 (4)0.046 (4)−0.005 (4)
N30.0560 (16)0.0452 (14)0.0440 (13)0.0098 (11)0.0010 (11)0.0010 (11)
N40.0665 (18)0.0561 (17)0.0478 (14)0.0159 (13)−0.0152 (12)−0.0044 (12)
O30.0578 (13)0.0470 (12)0.0448 (11)0.0087 (10)−0.0013 (10)−0.0052 (9)
O40.103 (2)0.0658 (16)0.0503 (13)0.0144 (14)−0.0208 (13)−0.0160 (11)
C70.063 (2)0.0385 (17)0.066 (2)0.0086 (15)−0.0067 (17)0.0040 (15)
C80.088 (4)0.116 (4)0.184 (6)0.015 (3)−0.006 (4)0.074 (4)
C90.149 (7)0.209 (8)0.211 (8)−0.043 (6)0.074 (6)−0.073 (7)
N50.0499 (15)0.0462 (14)0.0543 (14)0.0042 (11)0.0049 (12)0.0054 (11)
N60.0617 (18)0.0450 (15)0.0650 (17)0.0019 (13)0.0032 (14)0.0135 (12)
O50.0494 (13)0.0451 (12)0.0654 (13)0.0044 (9)−0.0045 (10)0.0090 (10)
O60.0696 (18)0.0669 (17)0.152 (3)0.0096 (14)−0.0220 (18)0.0428 (17)
Ni20.0471 (2)0.0433 (2)0.04003 (19)0.00219 (16)−0.00265 (15)0.00044 (15)
C110.052 (2)0.056 (2)0.0480 (17)−0.0015 (15)−0.0010 (15)0.0084 (14)
C120.065 (3)0.130 (4)0.122 (4)0.016 (3)0.035 (3)0.055 (3)
C130.122 (4)0.106 (4)0.170 (5)−0.002 (3)0.074 (4)0.029 (4)
N110.0466 (14)0.0475 (14)0.0440 (13)0.0017 (11)0.0023 (11)−0.0042 (11)
N120.0534 (17)0.0475 (15)0.0687 (17)0.0072 (12)0.0046 (13)0.0159 (13)
O110.0489 (12)0.0590 (14)0.0520 (12)0.0097 (10)0.0053 (10)0.0113 (10)
O120.0631 (16)0.0813 (17)0.0829 (17)0.0032 (13)0.0171 (13)0.0314 (14)
C140.058 (2)0.0467 (19)0.0591 (19)0.0036 (15)−0.0003 (16)−0.0006 (15)
C150.152 (5)0.112 (4)0.176 (6)0.082 (4)−0.080 (5)−0.036 (4)
C160.210 (8)0.164 (7)0.164 (7)0.070 (6)−0.052 (6)0.009 (5)
N130.0511 (15)0.0504 (15)0.0438 (13)0.0014 (11)−0.0036 (11)−0.0037 (11)
N140.0571 (17)0.0492 (16)0.0566 (15)0.0047 (12)0.0006 (13)−0.0095 (12)
O130.0570 (14)0.0523 (13)0.0592 (13)0.0072 (10)−0.0150 (11)0.0006 (10)
O140.0826 (19)0.0653 (17)0.104 (2)0.0302 (14)−0.0172 (16)−0.0148 (14)
C170.071 (2)0.0429 (17)0.0410 (16)0.0004 (15)−0.0097 (15)0.0034 (13)
C180.137 (4)0.063 (3)0.070 (3)−0.035 (3)−0.013 (3)−0.010 (2)
C190.124 (5)0.134 (5)0.167 (6)−0.056 (4)−0.046 (4)0.026 (4)
N150.0592 (16)0.0478 (15)0.0447 (13)−0.0055 (12)−0.0034 (11)0.0015 (11)
N160.081 (2)0.0618 (18)0.0346 (12)−0.0138 (15)0.0013 (12)−0.0011 (11)
O150.0633 (14)0.0526 (13)0.0456 (12)−0.0088 (10)−0.0029 (10)−0.0015 (9)
O160.107 (2)0.0668 (16)0.0431 (12)−0.0217 (14)−0.0077 (12)−0.0066 (11)
N210.0588 (17)0.0517 (16)0.0372 (13)0.0036 (13)0.0005 (12)−0.0029 (11)
O210.0641 (15)0.0782 (17)0.0555 (13)−0.0017 (12)−0.0166 (11)−0.0032 (11)
O220.0901 (19)0.0786 (18)0.0626 (15)−0.0167 (14)−0.0026 (13)−0.0278 (13)
O230.091 (2)0.104 (2)0.0855 (19)0.0506 (18)−0.0087 (15)−0.0140 (16)
N310.0649 (18)0.0522 (17)0.0476 (15)−0.0040 (13)0.0011 (13)−0.0021 (13)
O310.0696 (15)0.0432 (12)0.0606 (13)−0.0031 (11)0.0027 (11)0.0028 (10)
O320.160 (3)0.0598 (17)0.0659 (16)−0.0157 (17)−0.0025 (17)−0.0126 (13)
O330.228 (4)0.115 (3)0.072 (2)−0.074 (3)0.053 (2)−0.0056 (18)
N410.0540 (17)0.0521 (17)0.0572 (15)−0.0012 (14)0.0091 (13)0.0035 (13)
O410.0794 (17)0.0554 (15)0.0709 (15)0.0011 (12)−0.0043 (13)−0.0107 (12)
O420.0631 (16)0.0480 (14)0.111 (2)0.0075 (12)−0.0006 (14)−0.0144 (13)
O430.0623 (17)0.091 (2)0.113 (2)0.0121 (14)−0.0181 (16)−0.0019 (16)
N510.0582 (18)0.0486 (16)0.0544 (16)0.0097 (12)0.0037 (14)−0.0034 (12)
O510.0750 (16)0.0711 (16)0.0505 (13)−0.0006 (12)−0.0125 (11)0.0134 (11)
O520.0616 (15)0.0911 (18)0.0472 (12)0.0203 (13)−0.0099 (11)0.0027 (11)
O530.0603 (17)0.112 (2)0.098 (2)−0.0084 (15)0.0240 (15)−0.0276 (17)

Geometric parameters (Å, °)

Ni1—O12.062 (2)C11—O111.231 (4)
Ni1—O52.065 (2)C11—N121.317 (4)
Ni1—N32.074 (2)C11—O121.319 (4)
Ni1—N52.082 (2)C12—C131.405 (6)
Ni1—O32.0843 (19)C12—O121.466 (5)
Ni1—N12.103 (2)C12—H12A0.9700
C1—O11.226 (4)C12—H12B0.9700
C1—O21.317 (4)C13—H13A0.9600
C1—N21.322 (4)C13—H13B0.9600
C2—C31.354 (7)C13—H13C0.9600
C2—O21.469 (5)N11—N121.395 (3)
C2—H2A0.9700N11—H11A0.9000
C2—H2B0.9700N11—H11B0.9000
C3—H3A0.9600N12—H120.8600
C3—H3B0.9600C14—O131.218 (4)
C3—H3C0.9600C14—O141.313 (4)
N1—N21.406 (3)C14—N141.339 (4)
N1—H1A0.9000C15—C161.307 (7)
N1—H1B0.9000C15—O141.476 (5)
N2—H20.8600C15—H15A0.9700
C4—O31.227 (3)C15—H15B0.9700
C4—N41.318 (4)C16—H16A0.9600
C4—O41.321 (3)C16—H16B0.9600
C5—O41.443 (4)C16—H16C0.9600
C5—C61.474 (7)N13—N141.409 (3)
C5—H5A0.9700N13—H13D0.9000
C5—H5B0.9700N13—H13E0.9000
C6—H6A0.9600N14—H140.8600
C6—H6B0.9600C17—O151.228 (4)
C6—H6C0.9600C17—N161.316 (4)
N3—N41.407 (3)C17—O161.329 (4)
N3—H3D0.9000C18—O161.434 (5)
N3—H3E0.9000C18—C191.463 (7)
N4—H40.8600C18—H18A0.9700
C7—O51.233 (4)C18—H18B0.9700
C7—O61.311 (4)C19—H19A0.9600
C7—N61.316 (4)C19—H19B0.9600
C8—C91.294 (8)C19—H19C0.9600
C8—O61.485 (6)N15—N161.411 (3)
C8—H8A0.9700N15—H15C0.9000
C8—H8B0.9700N15—H15D0.9000
C9—H9A0.9600N16—H160.8600
C9—H9B0.9600N21—O231.222 (3)
C9—H9C0.9600N21—O221.237 (3)
N5—N61.405 (3)N21—O211.243 (3)
N5—H5C0.9000N31—O331.202 (3)
N5—H5D0.9000N31—O321.220 (3)
N6—H60.8600N31—O311.251 (3)
Ni2—O132.056 (2)N41—O431.222 (3)
Ni2—O152.069 (2)N41—O421.237 (3)
Ni2—O112.071 (2)N41—O411.251 (3)
Ni2—N152.075 (2)N51—O531.230 (3)
Ni2—N112.086 (2)N51—O521.243 (3)
Ni2—N132.097 (2)N51—O511.248 (3)
O1—Ni1—O593.81 (8)O13—Ni2—N11168.92 (9)
O1—Ni1—N390.69 (9)O15—Ni2—N1190.74 (9)
O5—Ni1—N3174.19 (9)O11—Ni2—N1179.61 (9)
O1—Ni1—N5173.06 (9)N15—Ni2—N1197.04 (10)
O5—Ni1—N579.34 (9)O13—Ni2—N1379.20 (9)
N3—Ni1—N596.08 (10)O15—Ni2—N13171.66 (9)
O1—Ni1—O390.59 (8)O11—Ni2—N1391.06 (9)
O5—Ni1—O396.16 (8)N15—Ni2—N1395.86 (10)
N3—Ni1—O380.10 (9)N11—Ni2—N1397.00 (9)
N5—Ni1—O389.08 (9)O11—C11—N12123.6 (3)
O1—Ni1—N179.25 (9)O11—C11—O12123.6 (3)
O5—Ni1—N189.74 (9)N12—C11—O12112.8 (3)
N3—Ni1—N194.71 (10)C13—C12—O12110.2 (4)
N5—Ni1—N1101.64 (10)C13—C12—H12A109.6
O3—Ni1—N1168.59 (8)O12—C12—H12A109.6
O1—C1—O2124.3 (3)C13—C12—H12B109.6
O1—C1—N2124.0 (3)O12—C12—H12B109.6
O2—C1—N2111.6 (3)H12A—C12—H12B108.1
C3—C2—O2110.4 (5)C12—C13—H13A109.5
C3—C2—H2A109.6C12—C13—H13B109.5
O2—C2—H2A109.6H13A—C13—H13B109.5
C3—C2—H2B109.6C12—C13—H13C109.5
O2—C2—H2B109.6H13A—C13—H13C109.5
H2A—C2—H2B108.1H13B—C13—H13C109.5
C2—C3—H3A109.5N12—N11—Ni2107.44 (17)
C2—C3—H3B109.5N12—N11—H11A110.2
H3A—C3—H3B109.5Ni2—N11—H11A110.2
C2—C3—H3C109.5N12—N11—H11B110.2
H3A—C3—H3C109.5Ni2—N11—H11B110.2
H3B—C3—H3C109.5H11A—N11—H11B108.5
N2—N1—Ni1107.07 (16)C11—N12—N11118.0 (2)
N2—N1—H1A110.3C11—N12—H12121.0
Ni1—N1—H1A110.3N11—N12—H12121.0
N2—N1—H1B110.3C11—O11—Ni2111.2 (2)
Ni1—N1—H1B110.3C11—O12—C12117.1 (3)
H1A—N1—H1B108.6O13—C14—O14124.1 (3)
C1—N2—N1116.9 (2)O13—C14—N14123.8 (3)
C1—N2—H2121.5O14—C14—N14112.0 (3)
N1—N2—H2121.5C16—C15—O14113.3 (5)
C1—O1—Ni1111.78 (19)C16—C15—H15A108.9
C1—O2—C2118.2 (3)O14—C15—H15A108.9
O3—C4—N4124.0 (3)C16—C15—H15B108.9
O3—C4—O4124.6 (3)O14—C15—H15B108.9
N4—C4—O4111.4 (3)H15A—C15—H15B107.7
O4—C5—C6110.8 (4)C15—C16—H16A109.5
O4—C5—H5A109.5C15—C16—H16B109.5
C6—C5—H5A109.5H16A—C16—H16B109.5
O4—C5—H5B109.5C15—C16—H16C109.5
C6—C5—H5B109.5H16A—C16—H16C109.5
H5A—C5—H5B108.1H16B—C16—H16C109.5
C5—C6—H6A109.5N14—N13—Ni2106.29 (17)
C5—C6—H6B109.5N14—N13—H13D110.5
H6A—C6—H6B109.5Ni2—N13—H13D110.5
C5—C6—H6C109.5N14—N13—H13E110.5
H6A—C6—H6C109.5Ni2—N13—H13E110.5
H6B—C6—H6C109.5H13D—N13—H13E108.7
N4—N3—Ni1107.26 (17)C14—N14—N13115.3 (2)
N4—N3—H3D110.3C14—N14—H14122.4
Ni1—N3—H3D110.3N13—N14—H14122.4
N4—N3—H3E110.3C14—O13—Ni2111.5 (2)
Ni1—N3—H3E110.3C14—O14—C15114.3 (3)
H3D—N3—H3E108.5O15—C17—N16124.3 (3)
C4—N4—N3118.0 (2)O15—C17—O16124.1 (3)
C4—N4—H4121.0N16—C17—O16111.6 (3)
N3—N4—H4121.0O16—C18—C19112.0 (4)
C4—O3—Ni1110.56 (19)O16—C18—H18A109.2
C4—O4—C5117.5 (3)C19—C18—H18A109.2
O5—C7—O6124.6 (3)O16—C18—H18B109.2
O5—C7—N6123.9 (3)C19—C18—H18B109.2
O6—C7—N6111.5 (3)H18A—C18—H18B107.9
C9—C8—O6105.9 (7)C18—C19—H19A109.5
C9—C8—H8A110.5C18—C19—H19B109.5
O6—C8—H8A110.5H19A—C19—H19B109.5
C9—C8—H8B110.5C18—C19—H19C109.5
O6—C8—H8B110.5H19A—C19—H19C109.5
H8A—C8—H8B108.7H19B—C19—H19C109.5
C8—C9—H9A109.5N16—N15—Ni2107.28 (18)
C8—C9—H9B109.5N16—N15—H15C110.3
H9A—C9—H9B109.5Ni2—N15—H15C110.3
C8—C9—H9C109.5N16—N15—H15D110.3
H9A—C9—H9C109.5Ni2—N15—H15D110.3
H9B—C9—H9C109.5H15C—N15—H15D108.5
N6—N5—Ni1108.28 (18)C17—N16—N15117.2 (2)
N6—N5—H5C110.0C17—N16—H16121.4
Ni1—N5—H5C110.0N15—N16—H16121.4
N6—N5—H5D110.0C17—O15—Ni2110.7 (2)
Ni1—N5—H5D110.0C17—O16—C18117.8 (3)
H5C—N5—H5D108.4O23—N21—O22121.4 (3)
C7—N6—N5116.8 (3)O23—N21—O21119.1 (3)
C7—N6—H6121.6O22—N21—O21119.5 (3)
N5—N6—H6121.6O33—N31—O32120.8 (3)
C7—O5—Ni1111.7 (2)O33—N31—O31118.8 (3)
C7—O6—C8116.9 (3)O32—N31—O31120.3 (3)
O13—Ni2—O1593.74 (9)O43—N41—O42120.6 (3)
O13—Ni2—O1190.00 (9)O43—N41—O41120.0 (3)
O15—Ni2—O1193.39 (9)O42—N41—O41119.4 (3)
O13—Ni2—N1593.71 (10)O53—N51—O52121.5 (3)
O15—Ni2—N1580.05 (9)O53—N51—O51118.6 (3)
O11—Ni2—N15172.65 (9)O52—N51—O51119.9 (3)
O1—Ni1—N1—N2−8.35 (17)O13—Ni2—N11—N1224.1 (6)
O5—Ni1—N1—N285.58 (18)O15—Ni2—N11—N12−89.82 (18)
N3—Ni1—N1—N2−98.16 (18)O11—Ni2—N11—N123.49 (18)
N5—Ni1—N1—N2164.63 (17)N15—Ni2—N11—N12−169.89 (18)
O3—Ni1—N1—N2−35.8 (6)N13—Ni2—N11—N1293.28 (19)
O1—C1—N2—N1−4.5 (5)O11—C11—N12—N111.3 (5)
O2—C1—N2—N1176.8 (3)O12—C11—N12—N11−178.2 (3)
Ni1—N1—N2—C19.5 (3)Ni2—N11—N12—C11−3.7 (3)
O2—C1—O1—Ni1175.0 (3)N12—C11—O11—Ni22.1 (4)
N2—C1—O1—Ni1−3.6 (4)O12—C11—O11—Ni2−178.6 (3)
O5—Ni1—O1—C1−82.2 (2)O13—Ni2—O11—C11−179.2 (2)
N3—Ni1—O1—C1101.5 (2)O15—Ni2—O11—C1187.0 (2)
O3—Ni1—O1—C1−178.4 (2)N11—Ni2—O11—C11−3.1 (2)
N1—Ni1—O1—C16.8 (2)N13—Ni2—O11—C11−100.0 (2)
O1—C1—O2—C25.4 (5)O11—C11—O12—C12−1.8 (5)
N2—C1—O2—C2−175.9 (4)N12—C11—O12—C12177.6 (3)
C3—C2—O2—C1107.9 (5)C13—C12—O12—C11172.5 (4)
O1—Ni1—N3—N490.63 (19)O13—Ni2—N13—N1416.10 (17)
N5—Ni1—N3—N4−87.85 (19)O11—Ni2—N13—N14−73.70 (18)
O3—Ni1—N3—N40.15 (18)N15—Ni2—N13—N14108.78 (18)
N1—Ni1—N3—N4169.90 (19)N11—Ni2—N13—N14−153.36 (17)
O3—C4—N4—N3−2.2 (5)O13—C14—N14—N1313.9 (5)
O4—C4—N4—N3178.2 (3)O14—C14—N14—N13−167.6 (3)
Ni1—N3—N4—C40.9 (3)Ni2—N13—N14—C14−20.5 (3)
N4—C4—O3—Ni12.2 (4)O14—C14—O13—Ni2−176.5 (3)
O4—C4—O3—Ni1−178.3 (3)N14—C14—O13—Ni21.8 (4)
O1—Ni1—O3—C4−91.8 (2)O15—Ni2—O13—C14173.9 (2)
O5—Ni1—O3—C4174.3 (2)O11—Ni2—O13—C1480.5 (2)
N3—Ni1—O3—C4−1.2 (2)N15—Ni2—O13—C14−105.8 (2)
N5—Ni1—O3—C495.2 (2)N11—Ni2—O13—C1460.3 (6)
N1—Ni1—O3—C4−64.9 (5)N13—Ni2—O13—C14−10.5 (2)
O3—C4—O4—C56.8 (5)O13—C14—O14—C15−7.3 (6)
N4—C4—O4—C5−173.7 (3)N14—C14—O14—C15174.2 (4)
C6—C5—O4—C4−88.4 (5)C16—C15—O14—C14−174.9 (6)
O5—Ni1—N5—N60.67 (18)O13—Ni2—N15—N16−98.25 (19)
N3—Ni1—N5—N6177.06 (18)O15—Ni2—N15—N16−5.10 (18)
O3—Ni1—N5—N697.12 (18)N11—Ni2—N15—N1684.42 (19)
N1—Ni1—N5—N6−86.84 (19)N13—Ni2—N15—N16−177.75 (19)
O5—C7—N6—N50.0 (5)O15—C17—N16—N15−1.0 (5)
O6—C7—N6—N5−180.0 (3)O16—C17—N16—N15178.7 (2)
Ni1—N5—N6—C7−0.6 (3)Ni2—N15—N16—C175.1 (3)
O6—C7—O5—Ni1−179.4 (3)N16—C17—O15—Ni2−3.8 (4)
N6—C7—O5—Ni10.6 (4)O16—C17—O15—Ni2176.6 (2)
O1—Ni1—O5—C7−179.6 (2)O13—Ni2—O15—C1798.0 (2)
N5—Ni1—O5—C7−0.7 (2)O11—Ni2—O15—C17−171.7 (2)
O3—Ni1—O5—C7−88.6 (2)N15—Ni2—O15—C174.9 (2)
N1—Ni1—O5—C7101.2 (2)N11—Ni2—O15—C17−92.1 (2)
O5—C7—O6—C818.3 (6)O15—C17—O16—C18−6.1 (5)
N6—C7—O6—C8−161.7 (4)N16—C17—O16—C18174.2 (3)
C9—C8—O6—C7−96.9 (6)C19—C18—O16—C1787.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O21i0.902.413.158 (3)140
N1—H1A···O22i0.902.583.419 (4)156
N1—H1B···O21ii0.902.323.073 (3)142
N1—H1B···O23ii0.902.403.280 (4)165
N2—H2···O52ii0.862.142.872 (3)143
N3—H3D···O510.902.163.019 (4)159
N3—H3E···O41i0.902.323.047 (3)138
N3—H3E···O43i0.902.553.435 (4)170
N4—H4···O310.862.122.951 (3)162
N5—H5C···O520.902.012.908 (3)172
N5—H5D···O420.902.173.064 (4)177
N6—H6···O210.862.303.096 (4)154
N11—H11A···O31iii0.902.173.071 (3)177
N11—H11B···O220.902.172.989 (3)151
N12—H12···O51iii0.862.192.960 (3)150
N13—H13D···O230.902.263.046 (4)146
N13—H13E···O420.902.303.091 (4)146
N14—H14···O530.862.252.984 (4)143
N15—H15C···O320.902.203.077 (4)165
N15—H15D···O410.902.102.951 (4)157
N16—H16···O31iv0.862.132.962 (3)163
N16—H16···O32iv0.862.403.113 (4)141

Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2208).

References

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  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
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