metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Bis{5-meth­oxy-2-[(2-morpholino­ethyl)imino­methyl-κN]phenolato-κO1}nickel(II)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 1 June 2009; accepted 2 June 2009; online 6 June 2009)

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

The Schiff base exists in the zwitterionic form; see: Mohd Lair et al. (2009[Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o1067.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C14H19N2O3)2]

  • Mr = 585.33

  • Triclinic, [P \overline 1]

  • a = 10.3358 (1) Å

  • b = 10.4502 (1) Å

  • c = 14.8764 (2) Å

  • α = 72.482 (1)°

  • β = 78.847 (1)°

  • γ = 61.926 (1)°

  • V = 1349.45 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.77 mm−1

  • T = 100 K

  • 0.45 × 0.35 × 0.25 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.724, Tmax = 0.831

  • 10299 measured reflections

  • 5978 independent reflections

  • 5388 reflections with I > 2σ(I)

  • Rint = 0.014

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.079

  • S = 1.02

  • 5978 reflections

  • 357 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Selected bond lengths (Å)

Ni1—O1 1.9001 (9)
Ni1—N1 2.0077 (10)
Ni2—O4 1.8873 (9)
Ni2—N3 2.0105 (10)

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-211.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 m3
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 mm1
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)
Graphite monochromatorRint = 0.014
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.724, Tmax = 0.831k = 1313
10299 measured reflectionsl = 1918
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 Å3
0 restraintsΔρmin = 0.45 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 1.02Δρmax = 0.24 e Å3
5978 reflectionsΔρmin = 0.45 e Å3
357 parameters
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)
O60.43863 (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)
N40.25854 (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)
H40.67290.00130.26770.024*
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)
H13A0.01270.51810.89840.026*
H13B0.01880.38840.86580.026*
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)
H180.27800.08120.32200.022*
C190.17215 (14)0.03538 (13)0.42195 (9)0.0175 (2)
H190.16150.04550.46780.021*
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*
C230.04492 (14)0.27936 (13)0.67398 (9)0.0175 (2)
H23A0.00000.31750.70620.021*
H23B0.01060.17100.70280.021*
C240.21159 (14)0.35923 (14)0.68823 (9)0.0183 (3)
H24A0.24810.46090.64590.022*
H24B0.25530.30420.67090.022*
C250.22424 (19)0.22319 (15)0.85116 (10)0.0287 (3)
H25A0.11650.16140.85060.034*
H25B0.26850.17150.83070.034*
C260.2839 (2)0.24170 (16)0.94997 (10)0.0335 (4)
H26A0.25910.14210.99390.040*
H26B0.23730.29100.97080.040*
C270.47234 (17)0.47365 (16)0.89310 (10)0.0264 (3)
H27A0.42710.52230.91590.032*
H27B0.58010.53540.89560.032*
C280.41669 (15)0.46615 (16)0.79223 (10)0.0224 (3)
H28A0.46900.42660.76730.027*
H28B0.43780.56810.75290.027*
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, º) 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—C1162.51 (11)C13—O3—C12—C1158.29 (14)
N1—Ni1—O1—C117.49 (11)N2—C11—C12—O360.30 (15)
N3ii—Ni2—O4—C15173.30 (12)C12—O3—C13—C1456.79 (14)
N3—Ni2—O4—C156.70 (12)C11—N2—C14—C1357.87 (14)
O1i—Ni1—N1—C8166.44 (11)C10—N2—C14—C13179.90 (11)
O1—Ni1—N1—C813.56 (11)O3—C13—C14—N257.68 (15)
O1i—Ni1—N1—C910.58 (9)Ni2—O4—C15—C16170.87 (9)
O1—Ni1—N1—C9169.42 (9)Ni2—O4—C15—C208.59 (19)
O4ii—Ni2—N3—C22177.97 (11)O4—C15—C16—C17179.89 (11)
O4—Ni2—N3—C222.03 (11)C20—C15—C16—C170.63 (18)
O4ii—Ni2—N3—C232.22 (9)C21—O5—C17—C168.00 (18)
O4—Ni2—N3—C23177.78 (9)C21—O5—C17—C18171.33 (11)
Ni1—O1—C1—C2166.26 (9)C15—C16—C17—O5178.45 (12)
Ni1—O1—C1—C612.93 (19)C15—C16—C17—C180.85 (19)
O1—C1—C2—C3177.25 (12)O5—C17—C18—C19177.94 (12)
C6—C1—C2—C31.99 (18)C16—C17—C18—C191.43 (19)
C7—O2—C3—C26.01 (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—C22175.93 (12)
C1—C2—C3—C43.39 (19)O4—C15—C20—C19179.04 (12)
O2—C3—C4—C5177.91 (11)C16—C15—C20—C191.50 (18)
C2—C3—C4—C52.23 (19)O4—C15—C20—C224.20 (19)
C3—C4—C5—C60.3 (2)C16—C15—C20—C22175.25 (12)
C4—C5—C6—C11.59 (19)C23—N3—C22—C20175.40 (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—N30.3 (2)
O1—C1—C6—C81.3 (2)C22—N3—C23—C24108.75 (12)
C2—C1—C6—C8179.52 (11)Ni2—N3—C23—C2475.15 (12)
C9—N1—C8—C6176.67 (12)C28—N4—C24—C23171.84 (10)
Ni1—N1—C8—C66.13 (19)C25—N4—C24—C2366.25 (14)
C5—C6—C8—N1176.71 (12)N3—C23—C24—N4165.34 (10)
C1—C6—C8—N14.2 (2)C24—N4—C25—C26176.26 (12)
C8—N1—C9—C10101.55 (13)C28—N4—C25—C2654.79 (17)
Ni1—N1—C9—C1081.20 (11)C27—O6—C26—C2561.61 (15)
C11—N2—C10—C9167.06 (10)N4—C25—C26—O660.01 (17)
C14—N2—C10—C972.06 (13)C26—O6—C27—C2859.59 (16)
N1—C9—C10—N2175.82 (10)C24—N4—C28—C27176.61 (11)
C10—N2—C11—C12177.93 (10)C25—N4—C28—C2753.46 (15)
C14—N2—C11—C1258.71 (13)O6—C27—C28—N456.47 (16)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Ni(C14H19N2O3)2]
Mr585.33
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.3358 (1), 10.4502 (1), 14.8764 (2)
α, β, γ (°)72.482 (1), 78.847 (1), 61.926 (1)
V3)1349.45 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.77
Crystal size (mm)0.45 × 0.35 × 0.25
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.724, 0.831
No. of measured, independent and
observed [I > 2σ(I)] reflections
10299, 5978, 5388
Rint0.014
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.079, 1.02
No. of reflections5978
No. of parameters357
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.45

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top
Ni1—O11.9001 (9)Ni2—O41.8873 (9)
Ni1—N12.0077 (10)Ni2—N32.0105 (10)
 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–211.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o1067.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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