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Acta Cryst. (2009). E65, m1556    [ doi:10.1107/S1600536809046145 ]

[4-Carboxyimidazole-5-carboxylato(2-)-[kappa]2N1,O5](5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-[kappa]4N,N',N'',N''')nickel(II) monohydrate

G.-C. Ou, Q. Zhou and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
[4-Carboxyimidazole-5-carboxylato(2-)- κ2N1,O5](5,5,7,12,12,14-hexamethyl-1,4,8,11- tetraazacyclotetradecane- κ4N,N',N'',N''')nickel(II) monohydrate top
Crystal data top
[Ni(C5H2N2O4)(C16H36N4)]·H2OF(000) = 1104
Mr = 515.30Dx = 1.387 Mg m−3
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 mm−1
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 top
Bruker SMART area-detector
diffractometer		4308 independent reflections
Radiation source: fine-focus sealed tube2809 reflections with I > 2σ(I)
graphiteRint = 0.046
φ 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 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.04 w = 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 Å−3
12 restraintsΔρmin = −0.36 e Å−3
Crystal data top
[Ni(C5H2N2O4)(C16H36N4)]·H2OV = 2467.7 (3) Å3
Mr = 515.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.4070 (8) ŵ = 0.83 mm−1
b = 12.7806 (10) ÅT = 295 K
c = 19.0947 (14) Å0.42 × 0.36 × 0.12 mm
β = 103.675 (1)°
Data collection top
Bruker SMART area-detector
diffractometer		4308 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2809 reflections with I > 2σ(I)
Tmin = 0.767, Tmax = 0.905Rint = 0.046
10408 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.163Δρmax = 0.70 e Å−3
S = 1.04Δρmin = −0.36 e Å−3
4308 reflectionsAbsolute structure: ?
309 parametersFlack parameter: ?
12 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Acknowledgements top

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).

references
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