supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

Acta Cryst. (2009). E65, m733    [ doi:10.1107/S1600536809020790 ]

Bis{5-methoxy-2-[(2-morpholinoethyl)iminomethyl-[kappa]N]phenolato-[kappa]O1}nickel(II)

N. Mohd Lair, H. Mohd Ali and S. W. Ng

Abstract top

The asymmetric unit of the crystal structure of the title compound, [Ni(C14H19N2O3)2], contains two independent NiII complex molecules, with the metal atoms each located on a center of inversion. Each metal atom is chelated by two Schiff base anions in a distorted square-planar coordination environment.

Related literature top

The Schiff base exists in the zwitterionic form; see: Mohd Lair et al. (2009).

Experimental top

The Schiff base was synthesized as described (Mohd Lair et al., 2009). The Schiff base (0.25 g, 2 mmol) and nickel(II) acetate (0.29 g, 1 mmol) were heated in ethanol (50 ml) for 5 hours. Large crystals appeared after a day.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 the two independent molecules of Ni(C14H19N2O3)2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Bis{5-methoxy-2-[(2-morpholinoethyl)iminomethyl-κN]phenolato- κO1}nickel(II) top
Crystal data top
[Ni(C14H19N2O3)2]Z = 2
Mr = 585.33F(000) = 620
Triclinic, P1Dx = 1.441 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.3358 (1) ÅCell parameters from 7081 reflections
b = 10.4502 (1) Åθ = 2.4–28.3°
c = 14.8764 (2) ŵ = 0.77 mm−1
α = 72.482 (1)°T = 100 K
β = 78.847 (1)°Block, brown
γ = 61.926 (1)°0.45 × 0.35 × 0.25 mm
V = 1349.45 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer		5978 independent reflections
Radiation source: fine-focus sealed tube5388 reflections with I > 2σ(I)
graphiteRint = 0.014
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.724, Tmax = 0.831k = −13→13
10299 measured reflectionsl = −19→18
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0486P)2 + 0.3802P]
where P = (Fo2 + 2Fc2)/3
5978 reflections(Δ/σ)max = 0.001
357 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.45 e Å−3
Crystal data top
[Ni(C14H19N2O3)2]γ = 61.926 (1)°
Mr = 585.33V = 1349.45 (3) Å3
Triclinic, P1Z = 2
a = 10.3358 (1) ÅMo Kα radiation
b = 10.4502 (1) ŵ = 0.77 mm−1
c = 14.8764 (2) ÅT = 100 K
α = 72.482 (1)°0.45 × 0.35 × 0.25 mm
β = 78.847 (1)°
Data collection top
Bruker SMART APEX
diffractometer		5978 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5388 reflections with I > 2σ(I)
Tmin = 0.724, Tmax = 0.831Rint = 0.014
10299 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.079Δρmax = 0.24 e Å−3
S = 1.02Δρmin = −0.45 e Å−3
5978 reflectionsAbsolute structure: ?
357 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.01251 (7)
Ni20.00000.50000.50000.01139 (7)
O10.64797 (11)0.38684 (10)0.41957 (7)0.0219 (2)
O20.85765 (11)0.09562 (10)0.19085 (7)0.0217 (2)
O30.11665 (11)0.31275 (11)0.96822 (7)0.0226 (2)
O40.07976 (11)0.42908 (10)0.38957 (6)0.0201 (2)
O50.33314 (11)0.09974 (10)0.18575 (7)0.0204 (2)
O6−0.43863 (13)0.32859 (12)0.95338 (8)0.0333 (3)
N10.40989 (12)0.35698 (11)0.53370 (7)0.0165 (2)
N20.25322 (12)0.28136 (11)0.78382 (8)0.0171 (2)
N30.00294 (12)0.30250 (11)0.57283 (7)0.0160 (2)
N4−0.25854 (12)0.37022 (11)0.78592 (8)0.0171 (2)
C10.65173 (14)0.28594 (14)0.38318 (9)0.0169 (2)
C20.75883 (14)0.24097 (13)0.30890 (9)0.0177 (3)
H20.82810.28120.28900.021*
C30.76314 (14)0.13913 (14)0.26538 (9)0.0175 (3)
C40.66694 (15)0.07116 (14)0.29655 (9)0.0199 (3)
H40.6729−0.00130.26770.024*
C50.56494 (14)0.11209 (13)0.36923 (9)0.0182 (3)
H50.50030.06640.39070.022*
C60.55269 (14)0.22006 (13)0.41341 (9)0.0163 (2)
C70.94834 (15)0.17079 (15)0.15000 (10)0.0242 (3)
H7A1.00630.13410.09490.036*
H7B1.01460.15110.19670.036*
H7C0.88620.27860.13040.036*
C80.44220 (14)0.25732 (13)0.48793 (9)0.0168 (2)
H80.38580.20250.50600.020*
C90.29494 (14)0.36405 (14)0.61125 (9)0.0175 (2)
H9A0.23770.31560.60200.021*
H9B0.22680.46980.61030.021*
C100.36353 (14)0.28583 (14)0.70611 (9)0.0179 (3)
H10A0.43730.18240.70490.022*
H10B0.41480.33890.71710.022*
C110.32412 (15)0.17738 (14)0.87014 (9)0.0202 (3)
H11A0.38740.21130.88900.024*
H11B0.38680.07670.85860.024*
C120.20802 (15)0.17037 (14)0.94837 (9)0.0219 (3)
H12A0.14670.13420.92960.026*
H12B0.25640.09811.00620.026*
C130.04749 (15)0.41852 (15)0.88474 (10)0.0220 (3)
H13A−0.01270.51810.89840.026*
H13B−0.01880.38840.86580.026*
C140.15997 (15)0.42874 (14)0.80402 (9)0.0195 (3)
H14A0.10890.50050.74690.023*
H14B0.22190.46590.82100.023*
C150.13013 (14)0.29600 (13)0.37536 (9)0.0156 (2)
C160.20321 (14)0.27219 (13)0.28691 (9)0.0162 (2)
H160.21440.35200.24020.019*
C170.25856 (14)0.13342 (14)0.26797 (9)0.0163 (2)
C180.24168 (14)0.01325 (14)0.33586 (9)0.0183 (3)
H180.2780−0.08120.32200.022*
C190.17215 (14)0.03538 (13)0.42195 (9)0.0175 (2)
H190.1615−0.04550.46780.021*
C200.11576 (13)0.17479 (13)0.44478 (9)0.0157 (2)
C210.37176 (15)0.21061 (15)0.11990 (9)0.0214 (3)
H21A0.43150.17070.06620.032*
H21B0.42800.23680.15120.032*
H21C0.28210.30000.09740.032*
C220.05326 (13)0.18669 (13)0.53806 (9)0.0158 (2)
H220.04790.09990.57940.019*
C23−0.04492 (14)0.27936 (13)0.67398 (9)0.0175 (2)
H23A0.00000.31750.70620.021*
H23B−0.01060.17100.70280.021*
C24−0.21159 (14)0.35923 (14)0.68823 (9)0.0183 (3)
H24A−0.24810.46090.64590.022*
H24B−0.25530.30420.67090.022*
C25−0.22424 (19)0.22319 (15)0.85116 (10)0.0287 (3)
H25A−0.11650.16140.85060.034*
H25B−0.26850.17150.83070.034*
C26−0.2839 (2)0.24170 (16)0.94997 (10)0.0335 (4)
H26A−0.25910.14210.99390.040*
H26B−0.23730.29100.97080.040*
C27−0.47234 (17)0.47365 (16)0.89310 (10)0.0264 (3)
H27A−0.42710.52230.91590.032*
H27B−0.58010.53540.89560.032*
C28−0.41669 (15)0.46615 (16)0.79223 (10)0.0224 (3)
H28A−0.46900.42660.76730.027*
H28B−0.43780.56810.75290.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01396 (11)0.01469 (11)0.01148 (12)−0.00886 (9)0.00226 (8)−0.00429 (8)
Ni20.01437 (11)0.00926 (11)0.01011 (12)−0.00527 (8)0.00115 (8)−0.00286 (8)
O10.0239 (5)0.0239 (5)0.0250 (5)−0.0154 (4)0.0058 (4)−0.0119 (4)
O20.0252 (5)0.0203 (5)0.0203 (5)−0.0112 (4)0.0053 (4)−0.0080 (4)
O30.0262 (5)0.0214 (5)0.0158 (5)−0.0079 (4)0.0025 (4)−0.0051 (4)
O40.0277 (5)0.0132 (4)0.0181 (5)−0.0089 (4)0.0029 (4)−0.0051 (3)
O50.0245 (5)0.0185 (4)0.0187 (5)−0.0098 (4)0.0050 (4)−0.0083 (4)
O60.0490 (7)0.0321 (6)0.0244 (6)−0.0273 (5)0.0166 (5)−0.0102 (4)
N10.0167 (5)0.0199 (5)0.0139 (5)−0.0098 (4)0.0014 (4)−0.0036 (4)
N20.0182 (5)0.0162 (5)0.0156 (5)−0.0077 (4)0.0016 (4)−0.0039 (4)
N30.0180 (5)0.0156 (5)0.0141 (5)−0.0078 (4)−0.0004 (4)−0.0030 (4)
N40.0209 (5)0.0157 (5)0.0137 (5)−0.0085 (4)0.0010 (4)−0.0027 (4)
C10.0187 (6)0.0156 (5)0.0156 (6)−0.0078 (5)−0.0017 (5)−0.0021 (4)
C20.0181 (6)0.0158 (6)0.0185 (6)−0.0084 (5)0.0004 (5)−0.0027 (5)
C30.0188 (6)0.0147 (6)0.0146 (6)−0.0052 (5)−0.0012 (5)−0.0013 (5)
C40.0239 (6)0.0185 (6)0.0196 (6)−0.0102 (5)−0.0026 (5)−0.0052 (5)
C50.0201 (6)0.0176 (6)0.0182 (6)−0.0104 (5)−0.0029 (5)−0.0017 (5)
C60.0181 (6)0.0157 (5)0.0144 (6)−0.0079 (5)−0.0025 (5)−0.0011 (4)
C70.0235 (7)0.0238 (7)0.0240 (7)−0.0115 (6)0.0067 (6)−0.0073 (5)
C80.0179 (6)0.0176 (6)0.0158 (6)−0.0097 (5)−0.0027 (5)−0.0008 (4)
C90.0166 (6)0.0217 (6)0.0168 (6)−0.0117 (5)0.0018 (5)−0.0046 (5)
C100.0169 (6)0.0211 (6)0.0171 (6)−0.0102 (5)0.0017 (5)−0.0049 (5)
C110.0211 (6)0.0183 (6)0.0177 (6)−0.0068 (5)0.0010 (5)−0.0040 (5)
C120.0266 (7)0.0192 (6)0.0170 (6)−0.0101 (5)0.0016 (5)−0.0024 (5)
C130.0214 (6)0.0215 (6)0.0184 (7)−0.0068 (5)0.0015 (5)−0.0044 (5)
C140.0213 (6)0.0168 (6)0.0185 (6)−0.0081 (5)0.0014 (5)−0.0040 (5)
C150.0152 (6)0.0143 (5)0.0175 (6)−0.0062 (5)−0.0023 (5)−0.0041 (4)
C160.0178 (6)0.0148 (5)0.0149 (6)−0.0068 (5)−0.0010 (5)−0.0028 (4)
C170.0148 (6)0.0187 (6)0.0160 (6)−0.0068 (5)−0.0008 (5)−0.0062 (5)
C180.0197 (6)0.0149 (5)0.0215 (7)−0.0074 (5)0.0001 (5)−0.0072 (5)
C190.0188 (6)0.0147 (5)0.0201 (6)−0.0088 (5)−0.0015 (5)−0.0029 (5)
C200.0158 (6)0.0153 (5)0.0170 (6)−0.0075 (5)−0.0020 (5)−0.0036 (5)
C210.0230 (7)0.0207 (6)0.0177 (6)−0.0090 (5)0.0027 (5)−0.0041 (5)
C220.0161 (6)0.0148 (5)0.0169 (6)−0.0081 (5)−0.0012 (5)−0.0022 (4)
C230.0219 (6)0.0156 (5)0.0136 (6)−0.0085 (5)0.0006 (5)−0.0021 (4)
C240.0206 (6)0.0206 (6)0.0158 (6)−0.0116 (5)0.0000 (5)−0.0035 (5)
C250.0451 (9)0.0177 (6)0.0179 (7)−0.0133 (6)0.0060 (6)−0.0025 (5)
C260.0531 (10)0.0207 (7)0.0174 (7)−0.0136 (7)0.0068 (7)−0.0021 (5)
C270.0274 (7)0.0302 (7)0.0207 (7)−0.0135 (6)0.0075 (6)−0.0090 (6)
C280.0206 (6)0.0297 (7)0.0189 (7)−0.0126 (6)0.0019 (5)−0.0082 (5)
Geometric parameters (Å, °) top
Ni1—O1i1.9001 (9)C9—H9A0.9900
Ni1—O11.9001 (9)C9—H9B0.9900
Ni1—N1i2.0077 (10)C10—H10A0.9900
Ni1—N12.0077 (10)C10—H10B0.9900
Ni2—O4ii1.8873 (9)C11—C121.5136 (18)
Ni2—O41.8873 (9)C11—H11A0.9900
Ni2—N3ii2.0105 (10)C11—H11B0.9900
Ni2—N32.0105 (10)C12—H12A0.9900
O1—C11.3052 (15)C12—H12B0.9900
O2—C31.3627 (16)C13—C141.5180 (18)
O2—C71.4319 (16)C13—H13A0.9900
O3—C121.4237 (16)C13—H13B0.9900
O3—C131.4312 (16)C14—H14A0.9900
O4—C151.3048 (15)C14—H14B0.9900
O5—C171.3613 (16)C15—C161.4140 (18)
O5—C211.4360 (15)C15—C201.4225 (16)
O6—C261.419 (2)C16—C171.3829 (17)
O6—C271.4244 (17)C16—H160.9500
N1—C81.2928 (17)C17—C181.4149 (17)
N1—C91.4786 (15)C18—C191.3697 (18)
N2—C111.4633 (16)C18—H180.9500
N2—C101.4650 (16)C19—C201.4141 (17)
N2—C141.4700 (16)C19—H190.9500
N3—C221.2974 (16)C20—C221.4281 (18)
N3—C231.4740 (16)C21—H21A0.9800
N4—C241.4614 (17)C21—H21B0.9800
N4—C281.4631 (17)C21—H21C0.9800
N4—C251.4667 (16)C22—H220.9500
C1—C21.4201 (18)C23—C241.5235 (18)
C1—C61.4223 (17)C23—H23A0.9900
C2—C31.3830 (18)C23—H23B0.9900
C2—H20.9500C24—H24A0.9900
C3—C41.4129 (18)C24—H24B0.9900
C4—C51.3698 (19)C25—C261.512 (2)
C4—H40.9500C25—H25A0.9900
C5—C61.4146 (17)C25—H25B0.9900
C5—H50.9500C26—H26A0.9900
C6—C81.4270 (18)C26—H26B0.9900
C7—H7A0.9800C27—C281.5109 (19)
C7—H7B0.9800C27—H27A0.9900
C7—H7C0.9800C27—H27B0.9900
C8—H80.9500C28—H28A0.9900
C9—C101.5197 (18)C28—H28B0.9900
O1i—Ni1—O1180.00 (5)O3—C12—H12B109.3
O1i—Ni1—N1i91.36 (4)C11—C12—H12B109.3
O1—Ni1—N1i88.64 (4)H12A—C12—H12B108.0
O1i—Ni1—N188.64 (4)O3—C13—C14111.45 (11)
O1—Ni1—N191.36 (4)O3—C13—H13A109.3
N1i—Ni1—N1180.000 (1)C14—C13—H13A109.3
O4ii—Ni2—O4180.000 (1)O3—C13—H13B109.3
O4ii—Ni2—N3ii91.43 (4)C14—C13—H13B109.3
O4—Ni2—N3ii88.57 (4)H13A—C13—H13B108.0
O4ii—Ni2—N388.57 (4)N2—C14—C13110.41 (10)
O4—Ni2—N391.43 (4)N2—C14—H14A109.6
N3ii—Ni2—N3180.00 (8)C13—C14—H14A109.6
C1—O1—Ni1129.48 (8)N2—C14—H14B109.6
C3—O2—C7117.40 (10)C13—C14—H14B109.6
C12—O3—C13109.77 (10)H14A—C14—H14B108.1
C15—O4—Ni2131.19 (8)O4—C15—C16117.97 (11)
C17—O5—C21117.05 (10)O4—C15—C20123.00 (12)
C26—O6—C27108.78 (11)C16—C15—C20119.02 (11)
C8—N1—C9115.10 (10)C17—C16—C15120.42 (11)
C8—N1—Ni1123.43 (9)C17—C16—H16119.8
C9—N1—Ni1121.41 (8)C15—C16—H16119.8
C11—N2—C10110.51 (10)O5—C17—C16124.33 (11)
C11—N2—C14108.13 (10)O5—C17—C18114.78 (11)
C10—N2—C14112.35 (10)C16—C17—C18120.89 (12)
C22—N3—C23115.73 (10)C19—C18—C17118.91 (11)
C22—N3—Ni2124.12 (9)C19—C18—H18120.5
C23—N3—Ni2120.03 (8)C17—C18—H18120.5
C24—N4—C28109.14 (10)C18—C19—C20122.07 (11)
C24—N4—C25111.97 (10)C18—C19—H19119.0
C28—N4—C25109.90 (11)C20—C19—H19119.0
O1—C1—C2118.41 (11)C19—C20—C15118.67 (12)
O1—C1—C6123.26 (12)C19—C20—C22118.84 (11)
C2—C1—C6118.33 (12)C15—C20—C22122.41 (11)
C3—C2—C1120.54 (12)O5—C21—H21A109.5
C3—C2—H2119.7O5—C21—H21B109.5
C1—C2—H2119.7H21A—C21—H21B109.5
O2—C3—C2124.17 (11)O5—C21—H21C109.5
O2—C3—C4114.60 (12)H21A—C21—H21C109.5
C2—C3—C4121.22 (12)H21B—C21—H21C109.5
C5—C4—C3118.52 (12)N3—C22—C20127.44 (11)
C5—C4—H4120.7N3—C22—H22116.3
C3—C4—H4120.7C20—C22—H22116.3
C4—C5—C6122.20 (12)N3—C23—C24111.20 (10)
C4—C5—H5118.9N3—C23—H23A109.4
C6—C5—H5118.9C24—C23—H23A109.4
C5—C6—C1119.11 (12)N3—C23—H23B109.4
C5—C6—C8118.53 (11)C24—C23—H23B109.4
C1—C6—C8122.35 (12)H23A—C23—H23B108.0
O2—C7—H7A109.5N4—C24—C23111.74 (11)
O2—C7—H7B109.5N4—C24—H24A109.3
H7A—C7—H7B109.5C23—C24—H24A109.3
O2—C7—H7C109.5N4—C24—H24B109.3
H7A—C7—H7C109.5C23—C24—H24B109.3
H7B—C7—H7C109.5H24A—C24—H24B107.9
N1—C8—C6127.62 (11)N4—C25—C26109.78 (11)
N1—C8—H8116.2N4—C25—H25A109.7
C6—C8—H8116.2C26—C25—H25A109.7
N1—C9—C10110.54 (10)N4—C25—H25B109.7
N1—C9—H9A109.5C26—C25—H25B109.7
C10—C9—H9A109.5H25A—C25—H25B108.2
N1—C9—H9B109.5O6—C26—C25111.08 (14)
C10—C9—H9B109.5O6—C26—H26A109.4
H9A—C9—H9B108.1C25—C26—H26A109.4
N2—C10—C9111.81 (10)O6—C26—H26B109.4
N2—C10—H10A109.3C25—C26—H26B109.4
C9—C10—H10A109.3H26A—C26—H26B108.0
N2—C10—H10B109.3O6—C27—C28111.46 (12)
C9—C10—H10B109.3O6—C27—H27A109.3
H10A—C10—H10B107.9C28—C27—H27A109.3
N2—C11—C12109.55 (11)O6—C27—H27B109.3
N2—C11—H11A109.8C28—C27—H27B109.3
C12—C11—H11A109.8H27A—C27—H27B108.0
N2—C11—H11B109.8N4—C28—C27111.16 (12)
C12—C11—H11B109.8N4—C28—H28A109.4
H11A—C11—H11B108.2C27—C28—H28A109.4
O3—C12—C11111.61 (10)N4—C28—H28B109.4
O3—C12—H12A109.3C27—C28—H28B109.4
C11—C12—H12A109.3H28A—C28—H28B108.0
N1i—Ni1—O1—C1−162.51 (11)C13—O3—C12—C1158.29 (14)
N1—Ni1—O1—C117.49 (11)N2—C11—C12—O3−60.30 (15)
N3ii—Ni2—O4—C15173.30 (12)C12—O3—C13—C14−56.79 (14)
N3—Ni2—O4—C15−6.70 (12)C11—N2—C14—C13−57.87 (14)
O1i—Ni1—N1—C8166.44 (11)C10—N2—C14—C13179.90 (11)
O1—Ni1—N1—C8−13.56 (11)O3—C13—C14—N257.68 (15)
O1i—Ni1—N1—C9−10.58 (9)Ni2—O4—C15—C16−170.87 (9)
O1—Ni1—N1—C9169.42 (9)Ni2—O4—C15—C208.59 (19)
O4ii—Ni2—N3—C22−177.97 (11)O4—C15—C16—C17−179.89 (11)
O4—Ni2—N3—C222.03 (11)C20—C15—C16—C170.63 (18)
O4ii—Ni2—N3—C23−2.22 (9)C21—O5—C17—C168.00 (18)
O4—Ni2—N3—C23177.78 (9)C21—O5—C17—C18−171.33 (11)
Ni1—O1—C1—C2166.26 (9)C15—C16—C17—O5−178.45 (12)
Ni1—O1—C1—C6−12.93 (19)C15—C16—C17—C180.85 (19)
O1—C1—C2—C3−177.25 (12)O5—C17—C18—C19177.94 (12)
C6—C1—C2—C31.99 (18)C16—C17—C18—C19−1.43 (19)
C7—O2—C3—C2−6.01 (18)C17—C18—C19—C200.51 (19)
C7—O2—C3—C4174.14 (11)C18—C19—C20—C150.94 (19)
C1—C2—C3—O2176.76 (11)C18—C19—C20—C22−175.93 (12)
C1—C2—C3—C4−3.39 (19)O4—C15—C20—C19179.04 (12)
O2—C3—C4—C5−177.91 (11)C16—C15—C20—C19−1.50 (18)
C2—C3—C4—C52.23 (19)O4—C15—C20—C22−4.20 (19)
C3—C4—C5—C60.3 (2)C16—C15—C20—C22175.25 (12)
C4—C5—C6—C1−1.59 (19)C23—N3—C22—C20−175.40 (12)
C4—C5—C6—C8179.30 (12)Ni2—N3—C22—C200.52 (19)
O1—C1—C6—C5179.65 (12)C19—C20—C22—N3176.48 (12)
C2—C1—C6—C50.45 (18)C15—C20—C22—N3−0.3 (2)
O1—C1—C6—C8−1.3 (2)C22—N3—C23—C24−108.75 (12)
C2—C1—C6—C8179.52 (11)Ni2—N3—C23—C2475.15 (12)
C9—N1—C8—C6−176.67 (12)C28—N4—C24—C23171.84 (10)
Ni1—N1—C8—C66.13 (19)C25—N4—C24—C23−66.25 (14)
C5—C6—C8—N1−176.71 (12)N3—C23—C24—N4−165.34 (10)
C1—C6—C8—N14.2 (2)C24—N4—C25—C26−176.26 (12)
C8—N1—C9—C10101.55 (13)C28—N4—C25—C26−54.79 (17)
Ni1—N1—C9—C10−81.20 (11)C27—O6—C26—C25−61.61 (15)
C11—N2—C10—C9167.06 (10)N4—C25—C26—O660.01 (17)
C14—N2—C10—C9−72.06 (13)C26—O6—C27—C2859.59 (16)
N1—C9—C10—N2−175.82 (10)C24—N4—C28—C27176.61 (11)
C10—N2—C11—C12−177.93 (10)C25—N4—C28—C2753.46 (15)
C14—N2—C11—C1258.71 (13)O6—C27—C28—N4−56.47 (16)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1.
Table 1
Selected geometric parameters (Å) top
Ni1—O11.9001 (9)Ni2—O41.8873 (9)
Ni1—N12.0077 (10)Ni2—N32.0105 (10)
Acknowledgements top

We thank the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–211.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o1067.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

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