PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m733.
Published online 2009 June 6. doi:  10.1107/S1600536809020790
PMCID: PMC2969209

Bis{5-methoxy-2-[(2-morpholinoethyl)iminomethyl-κN]phenolato-κO 1}nickel(II)

Abstract

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 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m733-scheme1.jpg

Experimental

Crystal data

  • [Ni(C14H19N2O3)2]
  • M r = 585.33
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m733-efi1.jpg
  • 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 [triangle]) T min = 0.724, T max = 0.831
  • 10299 measured reflections
  • 5978 independent reflections
  • 5388 reflections with I > 2σ(I)
  • R int = 0.014

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 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

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020790/xu2537sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020790/xu2537Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

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

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).

Figures

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.

Crystal data

[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

Bruker SMART APEX diffractometer5978 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

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 = 1.02w = 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

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

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)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2537).

References

  • 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. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography