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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): m1636.
Published online 2008 November 29. doi:  10.1107/S1600536808038749
PMCID: PMC2959799

trans-Bis(5,5-diphenyl­hydantoinato-κN 3)bis­(propane-1,2-diamine-κ2 N,N′)nickel(II)

Abstract

The asymmetric unit of the title complex, [Ni(pht)2(pn)2] (pht is 5,5-diphenyl­hydantoinate and pn is propane-1,2-diamine) or [Ni(C15H11N2O2)2(C3H10N2)2], contains one-half [Ni(pht)2(pn)2] mol­ecule. The NiII atom is situated on a crystallographic center of inversion and shows a distorted octa­hedral coordination geometry. A three-dimensional network structure is assembled by inter- and intra­molecular N—H(...)O=C inter­actions.

Related literature

For general background see Akitsu et al. (1997 [triangle]), Milne et al. (1999 [triangle]). For related structures see Akitsu & Einaga et al. (2005 [triangle]); Hu et al. (2006a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1636-scheme1.jpg

Experimental

Crystal data

  • [Ni(C15H11N2O2)2(C3H10N2)2]
  • M r = 709.49
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1636-efi1.jpg
  • a = 8.581 (1) Å
  • b = 9.731 (1) Å
  • c = 12.036 (2) Å
  • α = 100.602 (2)°
  • β = 90.298 (1)°
  • γ = 113.951 (2)°
  • V = 899.2 (2) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.59 mm−1
  • T = 298 (2) K
  • 0.47 × 0.45 × 0.36 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.769, T max = 0.816
  • 4760 measured reflections
  • 3164 independent reflections
  • 2908 reflections with I > 2σ(I)
  • R int = 0.011

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.074
  • S = 1.09
  • 3164 reflections
  • 253 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038749/im2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038749/im2088Isup2.hkl

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

Acknowledgments

We are grateful for financial support from the Key Project for Fundamental Research of the Educational Committee of Jiangsu Province (07 K J A15011) and the Natural Science Foundation of Huaihai Institute of Technology (KX07042).

supplementary crystallographic information

Comment

5,5-Diphenylimidazoline-2,4-dione (Hpht) is a widely used drug in the treatment of epilepsy. It should also be an excellent ligand for transition metal complexes (Milne et al.,1999; Akitsu et al.,1997; Akitsu & Einaga, 2005). We have therefore designed and synthesized a series of complexes with 5,5-diphenylhydantoinato ligands (Hu et al., 2006a).

The title compound (Fig. 1) consists of a neutral [Ni(pht)2(pn)2] complex molecule. The nickel atom is situated at the crystallographic center of inversion and is coordinated by two nitrogen atoms from two pht ligands and four nitrogen atoms from two pn ligands. The metal atom therefore adopts a distorted octahedral NiN6 coordination environment with a dihedral angle of 86.9 (1)° between N3—N3A—N4A—N4 and the hydantoin ring and dihedral angles between N3—N3A—N4A—N4 and the pht groups of 51.7 (1)° (C4 to C9) and 39.0 (1)° (C10 to C15), respectively. The Ni—N bond distances lie in the range of 2.096 (2) Å to 2.125 (2) Å. Intramolecular hydrogen bonds (Table 1) serve to stabilize the octahedral geometry. Adjacent molecules are linked by intermolecular hydrogen bonds along the crystallographic a axis. A similar hydrogen-bonding pattern is also found in the above-mentioned related complexes. The complex shows a three-dimensional network structure assembled by additional intermolecular N—H···O hydrogen bonds between the diamine ligand and the hydantoin ring.

Experimental

To a solution of Hpht (1.00 mmol) in methanol (10 ml) was added Ni(OAc)2 × 4 H2O (0.5 mmol) and a solution of propane-1,2-diamine (1 mmol) in methanol (10 ml). Then the mixture was sealed in a 25 ml PTFE-lined stainless steel autoclave and heated to 423 K for 40 h, the fill rate being 80%. After cooling to room temperature, purple single crystals of the title compound were obtained by slow evaporation from the filtrate. Analysis, calculated for C36H42N8NiO4: C 61.66, H 6.01, N 16.26; found: C 60.94, H 5.97, N 15.78%.

Refinement

The space group was assigned from the systematic absences. All H atoms were placed at calculated positions, with N—H = 0.86–0.89 Å and Uiso(H) values of 1.2Ueq(N), and C—H = 0.96 Å (methyl), 0.97 Å (methylene), 0.98 Å (methyne) and 0.93 Å (aryl), respectively, with Uiso(H) values of 1.2 Ueq(C) (methylene, methyne, aryl) or 1.5 Ueq(C) (methyl).

Figures

Fig. 1.
The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The crystal packing of the title complex.

Crystal data

[Ni(C15H11N2O2)2(C3H10N2)2]Z = 1
Mr = 709.49F000 = 374
Triclinic, P1Dx = 1.310 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.581 (1) ÅCell parameters from 3393 reflections
b = 9.731 (1) Åθ = 2.6–28.2º
c = 12.036 (2) ŵ = 0.59 mm1
α = 100.602 (2)ºT = 298 (2) K
β = 90.298 (1)ºBlock, violet
γ = 113.951 (2)º0.47 × 0.45 × 0.36 mm
V = 899.2 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3164 independent reflections
Radiation source: fine-focus sealed tube2908 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.011
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −7→10
Tmin = 0.769, Tmax = 0.816k = −11→11
4760 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.075  w = 1/[σ2(Fo2) + (0.0351P)2 + 0.2523P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
3164 reflectionsΔρmax = 0.17 e Å3
253 parametersΔρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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)
Ni10.50000.50000.50000.02926 (10)
N10.09328 (19)0.14829 (16)0.62697 (11)0.0390 (4)
H10.00970.05870.61400.047*
N20.31918 (17)0.35330 (15)0.59323 (11)0.0327 (3)
N30.70216 (19)0.52417 (18)0.61129 (13)0.0448 (4)
H3A0.77660.62350.63020.054*0.749 (12)
H3B0.66170.49230.67510.054*0.749 (12)
H3'A0.79900.60470.60390.054*0.251 (12)
H3'B0.67660.53640.68390.054*0.251 (12)
N40.5406 (2)0.31168 (17)0.41315 (13)0.0426 (4)
H4A0.44020.22910.39320.051*0.749 (12)
H4B0.59270.33330.34990.051*0.749 (12)
H4'A0.45810.22500.42720.051*0.251 (12)
H4'B0.53060.30810.33810.051*0.251 (12)
O10.17051 (16)0.14829 (14)0.44533 (10)0.0465 (3)
O20.39713 (17)0.50006 (14)0.77351 (10)0.0473 (3)
C10.1917 (2)0.21085 (18)0.54757 (13)0.0337 (4)
C20.3030 (2)0.38406 (18)0.70541 (13)0.0329 (4)
C30.1457 (2)0.25095 (18)0.73787 (13)0.0330 (4)
C40.0040 (2)0.3011 (2)0.77944 (14)0.0368 (4)
C50.0355 (3)0.4505 (2)0.82802 (17)0.0510 (5)
H50.14640.52650.83510.061*
C6−0.0972 (3)0.4891 (3)0.86675 (19)0.0635 (6)
H6−0.07400.59050.89910.076*
C7−0.2594 (3)0.3800 (3)0.85770 (19)0.0650 (6)
H7−0.34750.40640.88360.078*
C8−0.2934 (3)0.2302 (3)0.8102 (2)0.0712 (7)
H8−0.40470.15510.80430.085*
C9−0.1620 (3)0.1901 (3)0.7708 (2)0.0582 (5)
H9−0.18610.08840.73850.070*
C100.1974 (2)0.1815 (2)0.82832 (14)0.0370 (4)
C110.2842 (3)0.2747 (2)0.93080 (16)0.0503 (5)
H110.31190.37950.94340.060*
C120.3302 (3)0.2147 (3)1.01427 (19)0.0684 (6)
H120.38900.27901.08220.082*
C130.2896 (4)0.0616 (4)0.9973 (2)0.0843 (8)
H130.32120.02111.05330.101*
C140.2023 (4)−0.0325 (3)0.8978 (3)0.0929 (9)
H140.1736−0.13730.88660.112*
C150.1555 (3)0.0270 (2)0.8124 (2)0.0637 (6)
H150.0961−0.03810.74500.076*
C160.7858 (7)0.4340 (8)0.5562 (4)0.0575 (12)0.749 (12)
H16A0.85540.41800.61180.069*0.749 (12)
H16B0.86020.48730.50320.069*0.749 (12)
C170.6525 (7)0.2805 (5)0.4932 (5)0.0575 (12)0.749 (12)
H170.58120.22750.54870.069*0.749 (12)
C180.7400 (14)0.1808 (15)0.4340 (10)0.099 (3)0.749 (12)
H18A0.65510.07910.40380.148*0.749 (12)
H18B0.81970.17590.48770.148*0.749 (12)
H18C0.79990.22510.37340.148*0.749 (12)
C16'0.722 (2)0.368 (2)0.5724 (13)0.056 (4)0.251 (12)
H16C0.83320.38100.60200.068*0.251 (12)
H16D0.63560.28920.60480.068*0.251 (12)
C17'0.7033 (17)0.3156 (18)0.4444 (14)0.060 (3)0.251 (12)
H17'0.79590.38570.40810.072*0.251 (12)
C18'0.683 (4)0.149 (5)0.410 (3)0.103 (8)0.251 (12)
H18D0.59010.08390.44650.154*0.251 (12)
H18E0.78670.14220.43220.154*0.251 (12)
H18F0.65820.11510.32890.154*0.251 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.02461 (16)0.02656 (16)0.02889 (16)0.00303 (12)0.00163 (11)0.00520 (11)
N10.0362 (8)0.0296 (7)0.0283 (7)−0.0070 (6)0.0060 (6)0.0005 (6)
N20.0296 (7)0.0271 (7)0.0285 (7)−0.0002 (6)0.0031 (6)0.0033 (5)
N30.0354 (8)0.0493 (9)0.0422 (8)0.0079 (7)−0.0019 (7)0.0143 (7)
N40.0407 (9)0.0342 (8)0.0462 (9)0.0099 (7)0.0075 (7)0.0059 (7)
O10.0454 (8)0.0378 (7)0.0282 (6)−0.0079 (6)0.0059 (5)−0.0010 (5)
O20.0453 (7)0.0366 (7)0.0329 (6)−0.0059 (6)0.0031 (6)−0.0030 (5)
C10.0311 (9)0.0292 (8)0.0301 (8)0.0024 (7)0.0034 (7)0.0046 (7)
C20.0304 (9)0.0290 (8)0.0304 (8)0.0039 (7)0.0031 (7)0.0048 (7)
C30.0313 (9)0.0295 (8)0.0272 (8)0.0025 (7)0.0038 (7)0.0032 (6)
C40.0355 (9)0.0441 (10)0.0297 (8)0.0134 (8)0.0061 (7)0.0119 (7)
C50.0467 (11)0.0520 (12)0.0472 (11)0.0180 (10)0.0040 (9)−0.0008 (9)
C60.0677 (16)0.0705 (15)0.0572 (13)0.0382 (13)0.0098 (11)0.0017 (11)
C70.0620 (15)0.0929 (19)0.0575 (13)0.0471 (14)0.0196 (11)0.0201 (13)
C80.0395 (12)0.0841 (18)0.0908 (18)0.0206 (12)0.0208 (12)0.0308 (15)
C90.0409 (11)0.0533 (12)0.0777 (15)0.0136 (10)0.0168 (11)0.0209 (11)
C100.0328 (9)0.0395 (9)0.0354 (9)0.0107 (8)0.0108 (7)0.0102 (7)
C110.0544 (12)0.0543 (12)0.0382 (10)0.0192 (10)0.0011 (9)0.0078 (9)
C120.0703 (16)0.0855 (18)0.0460 (12)0.0272 (14)−0.0034 (11)0.0173 (12)
C130.099 (2)0.096 (2)0.0688 (17)0.0404 (18)−0.0025 (15)0.0412 (16)
C140.125 (3)0.0590 (16)0.100 (2)0.0353 (17)0.000 (2)0.0359 (16)
C150.0815 (17)0.0425 (12)0.0592 (13)0.0169 (11)−0.0027 (12)0.0126 (10)
C160.041 (2)0.068 (3)0.067 (2)0.024 (2)−0.0031 (18)0.021 (2)
C170.064 (3)0.054 (2)0.067 (3)0.036 (2)0.009 (2)0.0153 (19)
C180.106 (7)0.102 (6)0.111 (5)0.081 (6)−0.013 (4)−0.014 (4)
C16'0.053 (9)0.054 (8)0.071 (8)0.031 (7)−0.006 (6)0.014 (7)
C17'0.051 (6)0.080 (8)0.064 (8)0.039 (6)0.019 (5)0.021 (6)
C18'0.085 (16)0.099 (18)0.14 (2)0.063 (15)−0.022 (13)0.007 (15)

Geometric parameters (Å, °)

Ni1—N3i2.0946 (15)C6—H60.9300
Ni1—N32.0946 (15)C7—C81.371 (4)
Ni1—N42.0950 (15)C7—H70.9300
Ni1—N4i2.0950 (15)C8—C91.394 (3)
Ni1—N2i2.1245 (13)C8—H80.9300
Ni1—N22.1245 (13)C9—H90.9300
N1—C11.343 (2)C10—C151.372 (3)
N1—C31.456 (2)C10—C111.389 (3)
N1—H10.8600C11—C121.380 (3)
N2—C21.349 (2)C11—H110.9300
N2—C11.379 (2)C12—C131.359 (4)
N3—C161.423 (5)C12—H120.9300
N3—C16'1.580 (13)C13—C141.366 (4)
N3—H3A0.9000C13—H130.9300
N3—H3B0.9000C14—C151.398 (3)
N3—H3'A0.9000C14—H140.9300
N3—H3'B0.9000C15—H150.9300
N4—C17'1.428 (11)C16—C171.517 (8)
N4—C171.510 (4)C16—H16A0.9700
N4—H4A0.9000C16—H16B0.9700
N4—H4B0.9000C17—C181.534 (11)
N4—H4'A0.9000C17—H170.9800
N4—H4'B0.9000C18—H18A0.9600
O1—C11.245 (2)C18—H18B0.9600
O2—C21.2292 (19)C18—H18C0.9600
C2—C31.557 (2)C16'—C17'1.52 (3)
C3—C101.532 (2)C16'—H16C0.9700
C3—C41.538 (2)C16'—H16D0.9700
C4—C51.377 (3)C17'—C18'1.54 (4)
C4—C91.383 (3)C17'—H17'0.9800
C5—C61.393 (3)C18'—H18D0.9600
C5—H50.9300C18'—H18E0.9600
C6—C71.354 (3)C18'—H18F0.9600
N3i—Ni1—N3180.000 (1)C10—C3—C4109.20 (13)
N3i—Ni1—N496.99 (6)N1—C3—C298.65 (12)
N3—Ni1—N483.01 (6)C10—C3—C2111.63 (14)
N3i—Ni1—N4i83.01 (6)C4—C3—C2112.68 (14)
N3—Ni1—N4i96.99 (6)C5—C4—C9118.46 (18)
N4—Ni1—N4i180.00 (8)C5—C4—C3123.02 (16)
N3i—Ni1—N2i90.86 (6)C9—C4—C3118.48 (17)
N3—Ni1—N2i89.14 (6)C4—C5—C6120.7 (2)
N4—Ni1—N2i90.56 (6)C4—C5—H5119.7
N4i—Ni1—N2i89.44 (6)C6—C5—H5119.7
N3i—Ni1—N289.14 (6)C7—C6—C5120.5 (2)
N3—Ni1—N290.86 (6)C7—C6—H6119.7
N4—Ni1—N289.44 (6)C5—C6—H6119.7
N4i—Ni1—N290.56 (6)C6—C7—C8119.7 (2)
N2i—Ni1—N2180.00 (7)C6—C7—H7120.1
C1—N1—C3111.57 (13)C8—C7—H7120.1
C1—N1—H1124.2C7—C8—C9120.3 (2)
C3—N1—H1124.2C7—C8—H8119.8
C2—N2—C1107.79 (13)C9—C8—H8119.8
C2—N2—Ni1126.79 (11)C4—C9—C8120.2 (2)
C1—N2—Ni1125.37 (10)C4—C9—H9119.9
C16—N3—C16'26.9 (6)C8—C9—H9119.9
C16—N3—Ni1108.5 (2)C15—C10—C11118.31 (18)
C16'—N3—Ni1103.2 (5)C15—C10—C3121.58 (17)
C16—N3—H3A110.0C11—C10—C3120.09 (16)
C16'—N3—H3A134.1C12—C11—C10121.2 (2)
Ni1—N3—H3A110.0C12—C11—H11119.4
C16—N3—H3B110.0C10—C11—H11119.4
C16'—N3—H3B88.1C13—C12—C11120.0 (2)
Ni1—N3—H3B110.0C13—C12—H12120.0
H3A—N3—H3B108.4C11—C12—H12120.0
C16—N3—H3'A84.6C12—C13—C14119.7 (2)
C16'—N3—H3'A110.8C12—C13—H13120.1
Ni1—N3—H3'A111.2C14—C13—H13120.1
H3A—N3—H3'A27.1C13—C14—C15120.8 (2)
H3B—N3—H3'A128.4C13—C14—H14119.6
C16—N3—H3'B128.8C15—C14—H14119.6
C16'—N3—H3'B111.3C10—C15—C14119.9 (2)
Ni1—N3—H3'B111.2C10—C15—H15120.0
H3A—N3—H3'B85.3C14—C15—H15120.0
H3B—N3—H3'B24.9N3—C16—C17109.4 (4)
H3'A—N3—H3'B109.1N3—C16—H16A109.8
C17'—N4—C1730.6 (6)C17—C16—H16A109.8
C17'—N4—Ni1113.6 (5)N3—C16—H16B109.8
C17—N4—Ni1106.75 (19)C17—C16—H16B109.8
C17'—N4—H4A128.2H16A—C16—H16B108.2
C17—N4—H4A110.4N4—C17—C16107.8 (4)
Ni1—N4—H4A110.4N4—C17—C18113.7 (5)
C17'—N4—H4B80.3C16—C17—C18110.2 (6)
C17—N4—H4B110.4N4—C17—H17108.3
Ni1—N4—H4B110.4C16—C17—H17108.3
H4A—N4—H4B108.6C18—C17—H17108.3
C17'—N4—H4'A108.7C17'—C16'—N3113.0 (12)
C17—N4—H4'A84.0C17'—C16'—H16C109.0
Ni1—N4—H4'A108.7N3—C16'—H16C109.0
H4A—N4—H4'A29.0C17'—C16'—H16D109.0
H4B—N4—H4'A131.5N3—C16'—H16D109.0
C17'—N4—H4'B109.2H16C—C16'—H16D107.8
C17—N4—H4'B136.1N4—C17'—C16'102.5 (12)
Ni1—N4—H4'B108.9N4—C17'—C18'105.2 (14)
H4A—N4—H4'B80.1C16'—C17'—C18'112 (2)
H4B—N4—H4'B31.9N4—C17'—H17'112.3
H4'A—N4—H4'B107.6C16'—C17'—H17'112.3
O1—C1—N1124.25 (15)C18'—C17'—H17'112.3
O1—C1—N2124.13 (14)C17'—C18'—H18D109.5
N1—C1—N2111.62 (13)C17'—C18'—H18E109.5
O2—C2—N2125.70 (15)H18D—C18'—H18E109.5
O2—C2—C3124.01 (14)C17'—C18'—H18F109.5
N2—C2—C3110.29 (13)H18D—C18'—H18F109.5
N1—C3—C10113.28 (14)H18E—C18'—H18F109.5
N1—C3—C4111.15 (14)
N3i—Ni1—N2—C2−125.79 (15)O2—C2—C3—C465.1 (2)
N3—Ni1—N2—C254.21 (15)N2—C2—C3—C4−114.64 (15)
N4—Ni1—N2—C2137.22 (15)N1—C3—C4—C5−135.47 (17)
N4i—Ni1—N2—C2−42.78 (15)C10—C3—C4—C598.84 (19)
N2i—Ni1—N2—C24(100)C2—C3—C4—C5−25.8 (2)
N3i—Ni1—N2—C151.22 (14)N1—C3—C4—C946.6 (2)
N3—Ni1—N2—C1−128.78 (14)C10—C3—C4—C9−79.1 (2)
N4—Ni1—N2—C1−45.78 (14)C2—C3—C4—C9156.21 (17)
N4i—Ni1—N2—C1134.22 (14)C9—C4—C5—C6−0.5 (3)
N2i—Ni1—N2—C1−179 (100)C3—C4—C5—C6−178.45 (18)
N3i—Ni1—N3—C16122 (100)C4—C5—C6—C70.3 (3)
N4—Ni1—N3—C1615.4 (3)C5—C6—C7—C80.1 (4)
N4i—Ni1—N3—C16−164.6 (3)C6—C7—C8—C9−0.4 (4)
N2i—Ni1—N3—C16−75.2 (3)C5—C4—C9—C80.3 (3)
N2—Ni1—N3—C16104.8 (3)C3—C4—C9—C8178.32 (19)
N3i—Ni1—N3—C16'95 (100)C7—C8—C9—C40.2 (4)
N4—Ni1—N3—C16'−12.0 (8)N1—C3—C10—C15−15.7 (2)
N4i—Ni1—N3—C16'168.0 (8)C4—C3—C10—C15108.7 (2)
N2i—Ni1—N3—C16'−102.7 (8)C2—C3—C10—C15−126.00 (19)
N2—Ni1—N3—C16'77.3 (8)N1—C3—C10—C11166.25 (16)
N3i—Ni1—N4—C17'162.2 (9)C4—C3—C10—C11−69.3 (2)
N3—Ni1—N4—C17'−17.8 (9)C2—C3—C10—C1156.0 (2)
N4i—Ni1—N4—C17'−110 (100)C15—C10—C11—C121.0 (3)
N2i—Ni1—N4—C17'71.3 (9)C3—C10—C11—C12179.14 (19)
N2—Ni1—N4—C17'−108.7 (9)C10—C11—C12—C13−0.4 (4)
N3i—Ni1—N4—C17−165.9 (3)C11—C12—C13—C14−0.4 (5)
N3—Ni1—N4—C1714.1 (3)C12—C13—C14—C150.7 (5)
N4i—Ni1—N4—C17−78 (100)C11—C10—C15—C14−0.8 (4)
N2i—Ni1—N4—C17103.1 (3)C3—C10—C15—C14−178.9 (2)
N2—Ni1—N4—C17−76.9 (3)C13—C14—C15—C100.0 (5)
C3—N1—C1—O1−177.93 (17)C16'—N3—C16—C1740.6 (13)
C3—N1—C1—N21.9 (2)Ni1—N3—C16—C17−42.2 (6)
C2—N2—C1—O1179.86 (17)C17'—N4—C17—C1668.4 (11)
Ni1—N2—C1—O12.4 (3)Ni1—N4—C17—C16−39.8 (6)
C2—N2—C1—N10.0 (2)C17'—N4—C17—C18−54.1 (13)
Ni1—N2—C1—N1−177.47 (11)Ni1—N4—C17—C18−162.3 (7)
C1—N2—C2—O2178.50 (18)N3—C16—C17—N455.9 (7)
Ni1—N2—C2—O2−4.1 (3)N3—C16—C17—C18−179.5 (6)
C1—N2—C2—C3−1.79 (19)C16—N3—C16'—C17'−64.1 (18)
Ni1—N2—C2—C3175.64 (10)Ni1—N3—C16'—C17'40.7 (17)
C1—N1—C3—C10−120.79 (16)C17—N4—C17'—C16'−40.9 (13)
C1—N1—C3—C4115.83 (16)Ni1—N4—C17'—C16'42.2 (18)
C1—N1—C3—C2−2.67 (18)C17—N4—C17'—C18'76 (2)
O2—C2—C3—N1−177.60 (17)Ni1—N4—C17'—C18'159.0 (19)
N2—C2—C3—N12.68 (18)N3—C16'—C17'—N4−55 (2)
O2—C2—C3—C10−58.2 (2)N3—C16'—C17'—C18'−167.3 (14)
N2—C2—C3—C10122.05 (15)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3'B···O20.902.553.231 (2)133
N4—H4A···O10.902.262.983 (2)138

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2088).

References

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  • Hu, X., Xu, X., Xu, T. & Wang, D. (2006b). Acta Cryst. E62, m2221–m2223.
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