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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1556.
Published online 2009 November 11. doi:  10.1107/S1600536809046145
PMCID: PMC2972002

[4-Carboxy­imidazole-5-carboxyl­ato(2–)-κ2 N 1,O 5](5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­azacyclo­tetra­decane-κ4 N,N′,N′′,N′′′)nickel(II) monohydrate

Abstract

The 4-carboxy­imidazole-5-carboxyl­ate(2−) dianion in the title compound, [Ni(C5H2N2O4)(C16H36N4)]·H2O, N,O′-chelates to the NiII atom, which shows an octa­hedral coordination. The macrocycle folds itself around the metal atom and binds to it through four secondary nitrogen atoms; adjacent molecules are linked by N—H(...)O hydrogen bonds into a linear chain. The water molecule is disordered over two positions.

Related literature

For the crystal structures of other nickel salts of the macrocycle, see: Ou et al. (2009a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1556-scheme1.jpg

Experimental

Crystal data

  • [Ni(C5H2N2O4)(C16H36N4)]·H2O
  • M r = 515.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1556-efi1.jpg
  • a = 10.4070 (8) Å
  • b = 12.7806 (10) Å
  • c = 19.0947 (14) Å
  • β = 103.675 (1)°
  • V = 2467.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.83 mm−1
  • T = 295 K
  • 0.42 × 0.36 × 0.12 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.767, T max = 0.905
  • 10408 measured reflections
  • 4308 independent reflections
  • 2809 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.163
  • S = 1.04
  • 4308 reflections
  • 309 parameters
  • 12 restraints
  • H-atom parameters constrained
  • Δρmax = 0.70 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT-Plus (Bruker, 1999 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046145/xu2666sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046145/xu2666Isup2.hkl

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

Acknowledgments

This work was supported by the Foundation for University Key Teachers of the Education Department of Hunan Province and the Key Subject Construction Project of Hunan Province, China (No. 2006–180).

supplementary crystallographic information

Experimental

Imidazole-4,5-dicarboxylic acid (0.156 g, 1 mmol) and sodium hydroxide (0.080 g, 2 mmol) were dissolved in water (5 ml). To this solution was added (5,5,7,12,12,14 -hexamethyl-1,4,8,11-tetraazacyclotetradecane)nickel perchlorate (0.54 g, 1 mmol) dissolved in acetonitrile (10 ml). The solution was left to stand at room temperature; blue crystals formed after several weeks.

Refinement

Carbon-, nitrogen- and oxygen-bound H-atoms were positioned geometrically and refined using the riding model, and with C—H = 0.93 to 0.98 Å, N–H 0.86 Å, O–H 0.84 Å and U(H) set to 1.2–1.5 Ueq(C,N,O).

The water molecule does not form a hydrogen bond to other acceptor atoms. It is disordered over two positions in a 60:40 ratio. The anisotropic temperature factors were restrained to be nearly isotropic. The H-atoms were positioned so that there are no short H···H contacts.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of Ni(C16H36N4)(C5H2N2O4).H2O showing displacement ellipsoids of the 50% probability level. H-atoms are drawn as spheres of arbitrary radii.

Crystal data

[Ni(C5H2N2O4)(C16H36N4)]·H2OF(000) = 1104
Mr = 515.30Dx = 1.387 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2768 reflections
a = 10.4070 (8) Åθ = 2.6–24.5°
b = 12.7806 (10) ŵ = 0.83 mm1
c = 19.0947 (14) ÅT = 295 K
β = 103.675 (1)°Block, blue
V = 2467.7 (3) Å30.42 × 0.36 × 0.12 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer4308 independent reflections
Radiation source: fine-focus sealed tube2809 reflections with I > 2σ(I)
graphiteRint = 0.046
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.767, Tmax = 0.905k = −15→6
10408 measured reflectionsl = −22→22

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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0959P)2 + 0.1761P] where P = (Fo2 + 2Fc2)/3
4308 reflections(Δ/σ)max = 0.001
309 parametersΔρmax = 0.70 e Å3
12 restraintsΔρmin = −0.36 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Ni10.30812 (5)0.45585 (4)0.28750 (3)0.0245 (2)
O10.4614 (3)0.5510 (3)0.34989 (16)0.0336 (8)
O20.6725 (3)0.5949 (3)0.36493 (17)0.0376 (8)
O30.8653 (3)0.5250 (3)0.3258 (2)0.0538 (11)
H3O0.79970.54240.34170.081*
O40.9127 (4)0.4070 (3)0.2526 (3)0.0829 (16)
O1W0.7320 (8)0.3543 (8)0.0802 (4)0.073 (3)0.601 (16)
H1W10.71480.40420.10520.110*0.601 (16)
H1W20.68200.35460.03870.110*0.601 (16)
O1W'0.7294 (15)0.4398 (15)0.0802 (7)0.091 (6)0.399 (16)
H1W30.72970.48730.11070.136*0.399 (16)
H1W40.67850.45130.03970.136*0.399 (16)
N10.4737 (3)0.3997 (3)0.2535 (2)0.0305 (9)
N20.6458 (4)0.3371 (3)0.2133 (2)0.0426 (11)
N30.1845 (3)0.5172 (3)0.35147 (19)0.0278 (9)
H3N0.10820.48790.33810.033*
N40.2535 (4)0.5960 (3)0.22445 (19)0.0298 (9)
H4N0.31760.63890.24000.036*
N50.1663 (3)0.3764 (3)0.20915 (18)0.0267 (9)
H5N0.08970.39560.21400.032*
N60.3160 (3)0.3119 (3)0.34868 (19)0.0303 (9)
H6N0.38320.27830.34130.036*
C10.5726 (4)0.5398 (4)0.3369 (2)0.0304 (11)
C20.5852 (4)0.4563 (3)0.2869 (2)0.0261 (10)
C30.6903 (5)0.4169 (4)0.2603 (3)0.0380 (12)
C40.8316 (5)0.4491 (4)0.2793 (3)0.0464 (14)
C50.5175 (4)0.3311 (4)0.2119 (3)0.0360 (12)
H50.46200.28210.18390.043*
C60.1697 (4)0.6284 (4)0.3314 (3)0.0337 (11)
H6A0.25050.66570.35310.040*
H6B0.09820.65870.34920.040*
C70.1404 (4)0.6395 (4)0.2504 (2)0.0332 (11)
H7A0.06000.60190.22840.040*
H7B0.12790.71270.23710.040*
C80.2339 (4)0.5968 (4)0.1448 (2)0.0346 (12)
C90.3679 (5)0.5815 (4)0.1280 (3)0.0444 (13)
H9A0.42620.63690.14970.067*
H9B0.35820.58250.07670.067*
H9C0.40430.51550.14690.067*
C100.1777 (5)0.7000 (4)0.1105 (3)0.0493 (14)
H10A0.23630.75610.13030.074*
H10B0.09250.71210.12020.074*
H10C0.16880.69660.05930.074*
C110.1364 (5)0.5088 (4)0.1118 (2)0.0375 (12)
H11A0.05240.52450.12320.045*
H11B0.12240.51340.05980.045*
C120.1699 (4)0.3955 (4)0.1330 (2)0.0331 (11)
H120.26030.38230.12840.040*
C130.0766 (5)0.3224 (4)0.0799 (3)0.0425 (13)
H13A0.09810.25100.09310.064*
H13B0.08700.33460.03200.064*
H13C−0.01320.33620.08170.064*
C140.1822 (4)0.2652 (4)0.2291 (2)0.0319 (11)
H14A0.25890.23710.21500.038*
H14B0.10500.22640.20380.038*
C150.1992 (4)0.2524 (4)0.3093 (2)0.0353 (11)
H15A0.12070.27750.32300.042*
H15B0.21020.17890.32190.042*
C160.3346 (5)0.3134 (4)0.4296 (3)0.0367 (12)
C170.4744 (5)0.3503 (4)0.4619 (3)0.0428 (13)
H17A0.48660.41880.44390.064*
H17B0.53610.30260.44880.064*
H17C0.48920.35270.51340.064*
C180.3178 (5)0.2034 (4)0.4592 (3)0.0491 (14)
H18A0.38170.15680.44710.074*
H18B0.23030.17800.43820.074*
H18C0.33090.20670.51060.074*
C190.2315 (5)0.3859 (4)0.4496 (2)0.0375 (12)
H19A0.14470.35880.42670.045*
H19B0.24100.38080.50120.045*
C200.2335 (4)0.5008 (4)0.4307 (2)0.0318 (11)
H200.32550.52480.44450.038*
C210.1539 (5)0.5646 (4)0.4740 (3)0.0475 (14)
H21A0.18910.55310.52450.071*
H21B0.06300.54310.46100.071*
H21C0.15980.63770.46340.071*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0140 (3)0.0301 (3)0.0302 (3)−0.0013 (2)0.0066 (2)−0.0022 (3)
O10.0243 (17)0.048 (2)0.0290 (17)−0.0063 (15)0.0068 (13)−0.0025 (15)
O20.0233 (18)0.045 (2)0.0416 (19)−0.0127 (15)0.0028 (14)0.0012 (16)
O30.0214 (18)0.044 (2)0.097 (3)−0.0017 (17)0.015 (2)0.006 (2)
O40.031 (2)0.055 (3)0.174 (5)−0.006 (2)0.047 (3)−0.025 (3)
O1W0.091 (5)0.066 (7)0.076 (5)0.014 (4)0.047 (4)−0.015 (4)
O1W'0.117 (9)0.092 (11)0.081 (7)−0.016 (7)0.058 (6)0.004 (6)
N10.020 (2)0.036 (2)0.037 (2)0.0031 (17)0.0096 (17)0.0019 (19)
N20.026 (2)0.035 (2)0.073 (3)0.0018 (18)0.025 (2)−0.005 (2)
N30.0220 (19)0.033 (2)0.031 (2)−0.0021 (16)0.0121 (16)−0.0006 (17)
N40.022 (2)0.033 (2)0.032 (2)−0.0036 (17)0.0039 (16)−0.0001 (18)
N50.0155 (18)0.033 (2)0.032 (2)0.0015 (15)0.0064 (15)−0.0024 (17)
N60.022 (2)0.034 (2)0.036 (2)0.0042 (17)0.0088 (16)0.0037 (18)
C10.020 (2)0.037 (3)0.032 (3)−0.001 (2)0.0020 (19)0.010 (2)
C20.016 (2)0.029 (2)0.034 (2)−0.0014 (19)0.0083 (18)0.008 (2)
C30.025 (3)0.034 (3)0.058 (3)0.004 (2)0.015 (2)0.009 (3)
C40.026 (3)0.029 (3)0.090 (4)0.000 (2)0.025 (3)0.007 (3)
C50.029 (3)0.038 (3)0.044 (3)0.000 (2)0.015 (2)0.001 (2)
C60.025 (2)0.032 (3)0.046 (3)0.003 (2)0.013 (2)−0.005 (2)
C70.020 (2)0.030 (3)0.048 (3)0.002 (2)0.005 (2)0.002 (2)
C80.026 (3)0.044 (3)0.033 (3)−0.002 (2)0.004 (2)0.008 (2)
C90.043 (3)0.053 (3)0.040 (3)−0.006 (3)0.014 (2)0.006 (3)
C100.052 (3)0.048 (3)0.044 (3)−0.005 (3)0.004 (3)0.009 (3)
C110.028 (3)0.053 (3)0.029 (3)0.005 (2)0.003 (2)0.002 (2)
C120.022 (2)0.047 (3)0.031 (3)−0.002 (2)0.0092 (19)−0.004 (2)
C130.036 (3)0.053 (3)0.038 (3)−0.004 (2)0.007 (2)−0.011 (2)
C140.026 (2)0.033 (3)0.037 (3)−0.006 (2)0.009 (2)−0.006 (2)
C150.035 (3)0.028 (3)0.047 (3)−0.007 (2)0.018 (2)0.001 (2)
C160.034 (3)0.039 (3)0.039 (3)0.003 (2)0.013 (2)0.007 (2)
C170.031 (3)0.051 (3)0.044 (3)0.002 (2)0.004 (2)0.004 (3)
C180.054 (3)0.048 (3)0.050 (3)0.004 (3)0.021 (3)0.012 (3)
C190.037 (3)0.051 (3)0.027 (3)−0.003 (2)0.012 (2)0.001 (2)
C200.024 (2)0.048 (3)0.025 (2)−0.007 (2)0.0079 (19)−0.007 (2)
C210.052 (3)0.058 (4)0.035 (3)0.010 (3)0.014 (2)−0.005 (3)

Geometric parameters (Å, °)

Ni1—N52.098 (3)C8—C91.516 (7)
Ni1—N12.106 (4)C8—C101.527 (7)
Ni1—N32.123 (3)C8—C111.545 (7)
Ni1—O12.132 (3)C9—H9A0.9600
Ni1—N42.158 (4)C9—H9B0.9600
Ni1—N62.171 (4)C9—H9C0.9600
O1—C11.247 (5)C10—H10A0.9600
O2—C11.265 (5)C10—H10B0.9600
O3—C41.305 (6)C10—H10C0.9600
O3—H3O0.8400C11—C121.522 (7)
O4—C41.210 (6)C11—H11A0.9700
O1W—H1W10.8400C11—H11B0.9700
O1W—H1W20.8400C12—C131.541 (6)
O1W'—H1W30.8400C12—H120.9800
O1W'—H1W40.8400C13—H13A0.9600
N1—C51.333 (6)C13—H13B0.9600
N1—C21.388 (5)C13—H13C0.9600
N2—C51.331 (6)C14—C151.508 (6)
N2—C31.366 (6)C14—H14A0.9700
N3—C61.470 (6)C14—H14B0.9700
N3—C201.493 (5)C15—H15A0.9700
N3—H3N0.8600C15—H15B0.9700
N4—C81.485 (6)C16—C171.515 (6)
N4—C71.489 (5)C16—C191.533 (7)
N4—H4N0.8600C16—C181.541 (7)
N5—C141.471 (6)C17—H17A0.9600
N5—C121.484 (5)C17—H17B0.9600
N5—H5N0.8600C17—H17C0.9600
N6—C151.480 (6)C18—H18A0.9600
N6—C161.511 (6)C18—H18B0.9600
N6—H6N0.8600C18—H18C0.9600
C1—C21.458 (7)C19—C201.513 (7)
C2—C31.404 (6)C19—H19A0.9700
C3—C41.487 (7)C19—H19B0.9700
C5—H50.9300C20—C211.535 (6)
C6—C71.511 (6)C20—H200.9800
C6—H6A0.9700C21—H21A0.9600
C6—H6B0.9700C21—H21B0.9600
C7—H7A0.9700C21—H21C0.9600
C7—H7B0.9700
N5—Ni1—N195.99 (14)C10—C8—C11107.7 (4)
N5—Ni1—N399.73 (13)C8—C9—H9A109.5
N1—Ni1—N3162.72 (14)C8—C9—H9B109.5
N5—Ni1—O1169.03 (13)H9A—C9—H9B109.5
N1—Ni1—O178.92 (13)C8—C9—H9C109.5
N3—Ni1—O186.74 (13)H9A—C9—H9C109.5
N5—Ni1—N487.46 (14)H9B—C9—H9C109.5
N1—Ni1—N4103.71 (14)C8—C10—H10A109.5
N3—Ni1—N484.20 (14)C8—C10—H10B109.5
O1—Ni1—N484.36 (13)H10A—C10—H10B109.5
N5—Ni1—N684.52 (14)C8—C10—H10C109.5
N1—Ni1—N687.00 (14)H10A—C10—H10C109.5
N3—Ni1—N687.40 (14)H10B—C10—H10C109.5
O1—Ni1—N6104.75 (13)C12—C11—C8119.7 (4)
N4—Ni1—N6167.25 (14)C12—C11—H11A107.4
C1—O1—Ni1115.5 (3)C8—C11—H11A107.4
C4—O3—H3O109.5C12—C11—H11B107.4
H1W1—O1W—H1W2111.3C8—C11—H11B107.4
H1W3—O1W'—H1W4114.2H11A—C11—H11B106.9
C5—N1—C2104.5 (4)N5—C12—C11111.1 (4)
C5—N1—Ni1145.8 (3)N5—C12—C13112.7 (4)
C2—N1—Ni1109.7 (3)C11—C12—C13109.4 (4)
C5—N2—C3103.8 (4)N5—C12—H12107.8
C6—N3—C20112.9 (4)C11—C12—H12107.8
C6—N3—Ni1104.3 (2)C13—C12—H12107.8
C20—N3—Ni1115.0 (3)C12—C13—H13A109.5
C6—N3—H3N108.1C12—C13—H13B109.5
C20—N3—H3N108.1H13A—C13—H13B109.5
Ni1—N3—H3N108.1C12—C13—H13C109.5
C8—N4—C7114.2 (3)H13A—C13—H13C109.5
C8—N4—Ni1122.1 (3)H13B—C13—H13C109.5
C7—N4—Ni1104.4 (3)N5—C14—C15110.3 (4)
C8—N4—H4N104.9N5—C14—H14A109.6
C7—N4—H4N104.9C15—C14—H14A109.6
Ni1—N4—H4N104.9N5—C14—H14B109.6
C14—N5—C12112.7 (3)C15—C14—H14B109.6
C14—N5—Ni1105.4 (2)H14A—C14—H14B108.1
C12—N5—Ni1116.3 (3)N6—C15—C14110.2 (4)
C14—N5—H5N107.4N6—C15—H15A109.6
C12—N5—H5N107.4C14—C15—H15A109.6
Ni1—N5—H5N107.4N6—C15—H15B109.6
C15—N6—C16114.7 (3)C14—C15—H15B109.6
C15—N6—Ni1103.8 (3)H15A—C15—H15B108.1
C16—N6—Ni1121.2 (3)N6—C16—C17107.4 (4)
C15—N6—H6N105.2N6—C16—C19109.6 (4)
C16—N6—H6N105.2C17—C16—C19111.8 (4)
Ni1—N6—H6N105.2N6—C16—C18111.4 (4)
O1—C1—O2124.0 (5)C17—C16—C18108.4 (4)
O1—C1—C2116.5 (4)C19—C16—C18108.3 (4)
O2—C1—C2119.5 (4)C16—C17—H17A109.5
N1—C2—C3106.5 (4)C16—C17—H17B109.5
N1—C2—C1119.2 (4)H17A—C17—H17B109.5
C3—C2—C1134.3 (4)C16—C17—H17C109.5
N2—C3—C2109.5 (4)H17A—C17—H17C109.5
N2—C3—C4122.0 (4)H17B—C17—H17C109.5
C2—C3—C4128.5 (5)C16—C18—H18A109.5
O4—C4—O3121.0 (5)C16—C18—H18B109.5
O4—C4—C3121.4 (5)H18A—C18—H18B109.5
O3—C4—C3117.6 (5)C16—C18—H18C109.5
N2—C5—N1115.6 (4)H18A—C18—H18C109.5
N2—C5—H5122.2H18B—C18—H18C109.5
N1—C5—H5122.2C20—C19—C16118.5 (4)
N3—C6—C7110.0 (4)C20—C19—H19A107.7
N3—C6—H6A109.7C16—C19—H19A107.7
C7—C6—H6A109.7C20—C19—H19B107.7
N3—C6—H6B109.7C16—C19—H19B107.7
C7—C6—H6B109.7H19A—C19—H19B107.1
H6A—C6—H6B108.2N3—C20—C19110.9 (4)
N4—C7—C6108.7 (3)N3—C20—C21111.9 (4)
N4—C7—H7A109.9C19—C20—C21110.4 (4)
C6—C7—H7A109.9N3—C20—H20107.9
N4—C7—H7B109.9C19—C20—H20107.9
C6—C7—H7B109.9C21—C20—H20107.9
H7A—C7—H7B108.3C20—C21—H21A109.5
N4—C8—C9107.8 (4)C20—C21—H21B109.5
N4—C8—C10113.0 (4)H21A—C21—H21B109.5
C9—C8—C10107.4 (4)C20—C21—H21C109.5
N4—C8—C11109.3 (4)H21A—C21—H21C109.5
C9—C8—C11111.6 (4)H21B—C21—H21C109.5
N5—Ni1—O1—C1−58.3 (8)C5—N1—C2—C1179.8 (4)
N1—Ni1—O1—C14.9 (3)Ni1—N1—C2—C10.1 (5)
N3—Ni1—O1—C1175.2 (3)O1—C1—C2—N14.2 (6)
N4—Ni1—O1—C1−100.3 (3)O2—C1—C2—N1−176.7 (4)
N6—Ni1—O1—C188.8 (3)O1—C1—C2—C3−177.8 (5)
N5—Ni1—N1—C5−11.8 (6)O2—C1—C2—C31.2 (8)
N3—Ni1—N1—C5143.7 (6)C5—N2—C3—C20.7 (5)
O1—Ni1—N1—C5178.1 (6)C5—N2—C3—C4178.6 (5)
N4—Ni1—N1—C5−100.6 (6)N1—C2—C3—N2−1.3 (5)
N6—Ni1—N1—C572.4 (6)C1—C2—C3—N2−179.4 (5)
N5—Ni1—N1—C2167.8 (3)N1—C2—C3—C4−179.1 (5)
N3—Ni1—N1—C2−36.7 (6)C1—C2—C3—C42.8 (9)
O1—Ni1—N1—C2−2.3 (3)N2—C3—C4—O41.5 (8)
N4—Ni1—N1—C279.0 (3)C2—C3—C4—O4179.0 (5)
N6—Ni1—N1—C2−108.0 (3)N2—C3—C4—O3−178.7 (5)
N5—Ni1—N3—C6−103.8 (3)C2—C3—C4—O3−1.2 (8)
N1—Ni1—N3—C6101.1 (5)C3—N2—C5—N10.3 (6)
O1—Ni1—N3—C667.3 (3)C2—N1—C5—N2−1.1 (5)
N4—Ni1—N3—C6−17.3 (3)Ni1—N1—C5—N2178.5 (4)
N6—Ni1—N3—C6172.3 (3)C20—N3—C6—C7171.3 (3)
N5—Ni1—N3—C20132.0 (3)Ni1—N3—C6—C745.7 (4)
N1—Ni1—N3—C20−23.2 (6)C8—N4—C7—C6176.8 (4)
O1—Ni1—N3—C20−56.9 (3)Ni1—N4—C7—C641.0 (4)
N4—Ni1—N3—C20−141.6 (3)N3—C6—C7—N4−61.4 (5)
N6—Ni1—N3—C2048.0 (3)C7—N4—C8—C9163.5 (4)
N5—Ni1—N4—C8−44.3 (3)Ni1—N4—C8—C9−69.3 (4)
N1—Ni1—N4—C851.3 (3)C7—N4—C8—C1045.0 (5)
N3—Ni1—N4—C8−144.3 (3)Ni1—N4—C8—C10172.2 (3)
O1—Ni1—N4—C8128.4 (3)C7—N4—C8—C11−75.0 (5)
N6—Ni1—N4—C8−95.3 (7)Ni1—N4—C8—C1152.2 (4)
N5—Ni1—N4—C787.1 (3)N4—C8—C11—C12−60.0 (5)
N1—Ni1—N4—C7−177.4 (2)C9—C8—C11—C1259.2 (6)
N3—Ni1—N4—C7−13.0 (3)C10—C8—C11—C12176.8 (4)
O1—Ni1—N4—C7−100.3 (3)C14—N5—C12—C11173.0 (3)
N6—Ni1—N4—C736.1 (7)Ni1—N5—C12—C11−65.2 (4)
N1—Ni1—N5—C1470.1 (3)C14—N5—C12—C1349.8 (5)
N3—Ni1—N5—C14−102.7 (3)Ni1—N5—C12—C13171.6 (3)
O1—Ni1—N5—C14131.8 (6)C8—C11—C12—N568.9 (5)
N4—Ni1—N5—C14173.6 (3)C8—C11—C12—C13−166.0 (4)
N6—Ni1—N5—C14−16.3 (3)C12—N5—C14—C15171.1 (3)
N1—Ni1—N5—C12−55.5 (3)Ni1—N5—C14—C1543.4 (4)
N3—Ni1—N5—C12131.7 (3)C16—N6—C15—C14174.2 (4)
O1—Ni1—N5—C126.2 (9)Ni1—N6—C15—C1439.7 (4)
N4—Ni1—N5—C1248.0 (3)N5—C14—C15—N6−58.8 (5)
N6—Ni1—N5—C12−141.9 (3)C15—N6—C16—C17164.8 (4)
N5—Ni1—N6—C15−12.6 (3)Ni1—N6—C16—C17−69.3 (4)
N1—Ni1—N6—C15−109.0 (3)C15—N6—C16—C19−73.6 (5)
N3—Ni1—N6—C1587.4 (3)Ni1—N6—C16—C1952.4 (5)
O1—Ni1—N6—C15173.3 (3)C15—N6—C16—C1846.2 (5)
N4—Ni1—N6—C1538.6 (7)Ni1—N6—C16—C18172.2 (3)
N5—Ni1—N6—C16−143.4 (3)N6—C16—C19—C20−62.3 (5)
N1—Ni1—N6—C16120.3 (3)C17—C16—C19—C2056.6 (5)
N3—Ni1—N6—C16−43.3 (3)C18—C16—C19—C20176.0 (4)
O1—Ni1—N6—C1642.6 (3)C6—N3—C20—C19173.2 (4)
N4—Ni1—N6—C16−92.1 (7)Ni1—N3—C20—C19−67.2 (4)
Ni1—O1—C1—O2174.8 (3)C6—N3—C20—C2149.6 (5)
Ni1—O1—C1—C2−6.2 (5)Ni1—N3—C20—C21169.1 (3)
C5—N1—C2—C31.4 (5)C16—C19—C20—N372.5 (5)
Ni1—N1—C2—C3−178.4 (3)C16—C19—C20—C21−163.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3o···O20.841.642.468 (5)170
N5—H5n···O4i0.862.142.973 (5)162

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2666).

References

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  • Westrip, S. P. (2009). publCIF. In preparation.

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