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 ▶).
Experimental
Crystal data
[Ni(C14H19N2O3)2]
M r = 585.33
Triclinic,
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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 ▶).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020790/xu2537sup1.cif
e-65-0m733-sup1.cif (26.3KB, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020790/xu2537Isup2.hkl
e-65-0m733-Isup2.hkl (292.6KB, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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) |
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 = 585.33 | F(000) = 620 |
| Triclinic, P1 | Dx = 1.441 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.3358 (1) Å | Cell parameters from 7081 reflections |
| b = 10.4502 (1) Å | θ = 2.4–28.3° |
| c = 14.8764 (2) Å | µ = 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
| Bruker SMART APEX diffractometer | 5978 independent reflections |
| Radiation source: fine-focus sealed tube | 5388 reflections with I > 2σ(I) |
| graphite | Rint = 0.014 |
| ω scans | θmax = 27.5°, θmin = 1.4° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
| Tmin = 0.724, Tmax = 0.831 | k = −13→13 |
| 10299 measured reflections | l = −19→18 |
Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.079 | H-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 parameters | Δρmax = 0.24 e Å−3 |
| 0 restraints | Δρmin = −0.45 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.01251 (7) | |
| Ni2 | 0.0000 | 0.5000 | 0.5000 | 0.01139 (7) | |
| O1 | 0.64797 (11) | 0.38684 (10) | 0.41957 (7) | 0.0219 (2) | |
| O2 | 0.85765 (11) | 0.09562 (10) | 0.19085 (7) | 0.0217 (2) | |
| O3 | 0.11665 (11) | 0.31275 (11) | 0.96822 (7) | 0.0226 (2) | |
| O4 | 0.07976 (11) | 0.42908 (10) | 0.38957 (6) | 0.0201 (2) | |
| O5 | 0.33314 (11) | 0.09974 (10) | 0.18575 (7) | 0.0204 (2) | |
| O6 | −0.43863 (13) | 0.32859 (12) | 0.95338 (8) | 0.0333 (3) | |
| N1 | 0.40989 (12) | 0.35698 (11) | 0.53370 (7) | 0.0165 (2) | |
| N2 | 0.25322 (12) | 0.28136 (11) | 0.78382 (8) | 0.0171 (2) | |
| N3 | 0.00294 (12) | 0.30250 (11) | 0.57283 (7) | 0.0160 (2) | |
| N4 | −0.25854 (12) | 0.37022 (11) | 0.78592 (8) | 0.0171 (2) | |
| C1 | 0.65173 (14) | 0.28594 (14) | 0.38318 (9) | 0.0169 (2) | |
| C2 | 0.75883 (14) | 0.24097 (13) | 0.30890 (9) | 0.0177 (3) | |
| H2 | 0.8281 | 0.2812 | 0.2890 | 0.021* | |
| C3 | 0.76314 (14) | 0.13913 (14) | 0.26538 (9) | 0.0175 (3) | |
| C4 | 0.66694 (15) | 0.07116 (14) | 0.29655 (9) | 0.0199 (3) | |
| H4 | 0.6729 | −0.0013 | 0.2677 | 0.024* | |
| C5 | 0.56494 (14) | 0.11209 (13) | 0.36923 (9) | 0.0182 (3) | |
| H5 | 0.5003 | 0.0664 | 0.3907 | 0.022* | |
| C6 | 0.55269 (14) | 0.22006 (13) | 0.41341 (9) | 0.0163 (2) | |
| C7 | 0.94834 (15) | 0.17079 (15) | 0.15000 (10) | 0.0242 (3) | |
| H7A | 1.0063 | 0.1341 | 0.0949 | 0.036* | |
| H7B | 1.0146 | 0.1511 | 0.1967 | 0.036* | |
| H7C | 0.8862 | 0.2786 | 0.1304 | 0.036* | |
| C8 | 0.44220 (14) | 0.25732 (13) | 0.48793 (9) | 0.0168 (2) | |
| H8 | 0.3858 | 0.2025 | 0.5060 | 0.020* | |
| C9 | 0.29494 (14) | 0.36405 (14) | 0.61125 (9) | 0.0175 (2) | |
| H9A | 0.2377 | 0.3156 | 0.6020 | 0.021* | |
| H9B | 0.2268 | 0.4698 | 0.6103 | 0.021* | |
| C10 | 0.36353 (14) | 0.28583 (14) | 0.70611 (9) | 0.0179 (3) | |
| H10A | 0.4373 | 0.1824 | 0.7049 | 0.022* | |
| H10B | 0.4148 | 0.3389 | 0.7171 | 0.022* | |
| C11 | 0.32412 (15) | 0.17738 (14) | 0.87014 (9) | 0.0202 (3) | |
| H11A | 0.3874 | 0.2113 | 0.8890 | 0.024* | |
| H11B | 0.3868 | 0.0767 | 0.8586 | 0.024* | |
| C12 | 0.20802 (15) | 0.17037 (14) | 0.94837 (9) | 0.0219 (3) | |
| H12A | 0.1467 | 0.1342 | 0.9296 | 0.026* | |
| H12B | 0.2564 | 0.0981 | 1.0062 | 0.026* | |
| C13 | 0.04749 (15) | 0.41852 (15) | 0.88474 (10) | 0.0220 (3) | |
| H13A | −0.0127 | 0.5181 | 0.8984 | 0.026* | |
| H13B | −0.0188 | 0.3884 | 0.8658 | 0.026* | |
| C14 | 0.15997 (15) | 0.42874 (14) | 0.80402 (9) | 0.0195 (3) | |
| H14A | 0.1089 | 0.5005 | 0.7469 | 0.023* | |
| H14B | 0.2219 | 0.4659 | 0.8210 | 0.023* | |
| C15 | 0.13013 (14) | 0.29600 (13) | 0.37536 (9) | 0.0156 (2) | |
| C16 | 0.20321 (14) | 0.27219 (13) | 0.28691 (9) | 0.0162 (2) | |
| H16 | 0.2144 | 0.3520 | 0.2402 | 0.019* | |
| C17 | 0.25856 (14) | 0.13342 (14) | 0.26797 (9) | 0.0163 (2) | |
| C18 | 0.24168 (14) | 0.01325 (14) | 0.33586 (9) | 0.0183 (3) | |
| H18 | 0.2780 | −0.0812 | 0.3220 | 0.022* | |
| C19 | 0.17215 (14) | 0.03538 (13) | 0.42195 (9) | 0.0175 (2) | |
| H19 | 0.1615 | −0.0455 | 0.4678 | 0.021* | |
| C20 | 0.11576 (13) | 0.17479 (13) | 0.44478 (9) | 0.0157 (2) | |
| C21 | 0.37176 (15) | 0.21061 (15) | 0.11990 (9) | 0.0214 (3) | |
| H21A | 0.4315 | 0.1707 | 0.0662 | 0.032* | |
| H21B | 0.4280 | 0.2368 | 0.1512 | 0.032* | |
| H21C | 0.2821 | 0.3000 | 0.0974 | 0.032* | |
| C22 | 0.05326 (13) | 0.18669 (13) | 0.53806 (9) | 0.0158 (2) | |
| H22 | 0.0479 | 0.0999 | 0.5794 | 0.019* | |
| C23 | −0.04492 (14) | 0.27936 (13) | 0.67398 (9) | 0.0175 (2) | |
| H23A | 0.0000 | 0.3175 | 0.7062 | 0.021* | |
| H23B | −0.0106 | 0.1710 | 0.7028 | 0.021* | |
| C24 | −0.21159 (14) | 0.35923 (14) | 0.68823 (9) | 0.0183 (3) | |
| H24A | −0.2481 | 0.4609 | 0.6459 | 0.022* | |
| H24B | −0.2553 | 0.3042 | 0.6709 | 0.022* | |
| C25 | −0.22424 (19) | 0.22319 (15) | 0.85116 (10) | 0.0287 (3) | |
| H25A | −0.1165 | 0.1614 | 0.8506 | 0.034* | |
| H25B | −0.2685 | 0.1715 | 0.8307 | 0.034* | |
| C26 | −0.2839 (2) | 0.24170 (16) | 0.94997 (10) | 0.0335 (4) | |
| H26A | −0.2591 | 0.1421 | 0.9939 | 0.040* | |
| H26B | −0.2373 | 0.2910 | 0.9708 | 0.040* | |
| C27 | −0.47234 (17) | 0.47365 (16) | 0.89310 (10) | 0.0264 (3) | |
| H27A | −0.4271 | 0.5223 | 0.9159 | 0.032* | |
| H27B | −0.5801 | 0.5354 | 0.8956 | 0.032* | |
| C28 | −0.41669 (15) | 0.46615 (16) | 0.79223 (10) | 0.0224 (3) | |
| H28A | −0.4690 | 0.4266 | 0.7673 | 0.027* | |
| H28B | −0.4378 | 0.5681 | 0.7529 | 0.027* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.01396 (11) | 0.01469 (11) | 0.01148 (12) | −0.00886 (9) | 0.00226 (8) | −0.00429 (8) |
| Ni2 | 0.01437 (11) | 0.00926 (11) | 0.01011 (12) | −0.00527 (8) | 0.00115 (8) | −0.00286 (8) |
| O1 | 0.0239 (5) | 0.0239 (5) | 0.0250 (5) | −0.0154 (4) | 0.0058 (4) | −0.0119 (4) |
| O2 | 0.0252 (5) | 0.0203 (5) | 0.0203 (5) | −0.0112 (4) | 0.0053 (4) | −0.0080 (4) |
| O3 | 0.0262 (5) | 0.0214 (5) | 0.0158 (5) | −0.0079 (4) | 0.0025 (4) | −0.0051 (4) |
| O4 | 0.0277 (5) | 0.0132 (4) | 0.0181 (5) | −0.0089 (4) | 0.0029 (4) | −0.0051 (3) |
| O5 | 0.0245 (5) | 0.0185 (4) | 0.0187 (5) | −0.0098 (4) | 0.0050 (4) | −0.0083 (4) |
| O6 | 0.0490 (7) | 0.0321 (6) | 0.0244 (6) | −0.0273 (5) | 0.0166 (5) | −0.0102 (4) |
| N1 | 0.0167 (5) | 0.0199 (5) | 0.0139 (5) | −0.0098 (4) | 0.0014 (4) | −0.0036 (4) |
| N2 | 0.0182 (5) | 0.0162 (5) | 0.0156 (5) | −0.0077 (4) | 0.0016 (4) | −0.0039 (4) |
| N3 | 0.0180 (5) | 0.0156 (5) | 0.0141 (5) | −0.0078 (4) | −0.0004 (4) | −0.0030 (4) |
| N4 | 0.0209 (5) | 0.0157 (5) | 0.0137 (5) | −0.0085 (4) | 0.0010 (4) | −0.0027 (4) |
| C1 | 0.0187 (6) | 0.0156 (5) | 0.0156 (6) | −0.0078 (5) | −0.0017 (5) | −0.0021 (4) |
| C2 | 0.0181 (6) | 0.0158 (6) | 0.0185 (6) | −0.0084 (5) | 0.0004 (5) | −0.0027 (5) |
| C3 | 0.0188 (6) | 0.0147 (6) | 0.0146 (6) | −0.0052 (5) | −0.0012 (5) | −0.0013 (5) |
| C4 | 0.0239 (6) | 0.0185 (6) | 0.0196 (6) | −0.0102 (5) | −0.0026 (5) | −0.0052 (5) |
| C5 | 0.0201 (6) | 0.0176 (6) | 0.0182 (6) | −0.0104 (5) | −0.0029 (5) | −0.0017 (5) |
| C6 | 0.0181 (6) | 0.0157 (5) | 0.0144 (6) | −0.0079 (5) | −0.0025 (5) | −0.0011 (4) |
| C7 | 0.0235 (7) | 0.0238 (7) | 0.0240 (7) | −0.0115 (6) | 0.0067 (6) | −0.0073 (5) |
| C8 | 0.0179 (6) | 0.0176 (6) | 0.0158 (6) | −0.0097 (5) | −0.0027 (5) | −0.0008 (4) |
| C9 | 0.0166 (6) | 0.0217 (6) | 0.0168 (6) | −0.0117 (5) | 0.0018 (5) | −0.0046 (5) |
| C10 | 0.0169 (6) | 0.0211 (6) | 0.0171 (6) | −0.0102 (5) | 0.0017 (5) | −0.0049 (5) |
| C11 | 0.0211 (6) | 0.0183 (6) | 0.0177 (6) | −0.0068 (5) | 0.0010 (5) | −0.0040 (5) |
| C12 | 0.0266 (7) | 0.0192 (6) | 0.0170 (6) | −0.0101 (5) | 0.0016 (5) | −0.0024 (5) |
| C13 | 0.0214 (6) | 0.0215 (6) | 0.0184 (7) | −0.0068 (5) | 0.0015 (5) | −0.0044 (5) |
| C14 | 0.0213 (6) | 0.0168 (6) | 0.0185 (6) | −0.0081 (5) | 0.0014 (5) | −0.0040 (5) |
| C15 | 0.0152 (6) | 0.0143 (5) | 0.0175 (6) | −0.0062 (5) | −0.0023 (5) | −0.0041 (4) |
| C16 | 0.0178 (6) | 0.0148 (5) | 0.0149 (6) | −0.0068 (5) | −0.0010 (5) | −0.0028 (4) |
| C17 | 0.0148 (6) | 0.0187 (6) | 0.0160 (6) | −0.0068 (5) | −0.0008 (5) | −0.0062 (5) |
| C18 | 0.0197 (6) | 0.0149 (5) | 0.0215 (7) | −0.0074 (5) | 0.0001 (5) | −0.0072 (5) |
| C19 | 0.0188 (6) | 0.0147 (5) | 0.0201 (6) | −0.0088 (5) | −0.0015 (5) | −0.0029 (5) |
| C20 | 0.0158 (6) | 0.0153 (5) | 0.0170 (6) | −0.0075 (5) | −0.0020 (5) | −0.0036 (5) |
| C21 | 0.0230 (7) | 0.0207 (6) | 0.0177 (6) | −0.0090 (5) | 0.0027 (5) | −0.0041 (5) |
| C22 | 0.0161 (6) | 0.0148 (5) | 0.0169 (6) | −0.0081 (5) | −0.0012 (5) | −0.0022 (4) |
| C23 | 0.0219 (6) | 0.0156 (5) | 0.0136 (6) | −0.0085 (5) | 0.0006 (5) | −0.0021 (4) |
| C24 | 0.0206 (6) | 0.0206 (6) | 0.0158 (6) | −0.0116 (5) | 0.0000 (5) | −0.0035 (5) |
| C25 | 0.0451 (9) | 0.0177 (6) | 0.0179 (7) | −0.0133 (6) | 0.0060 (6) | −0.0025 (5) |
| C26 | 0.0531 (10) | 0.0207 (7) | 0.0174 (7) | −0.0136 (7) | 0.0068 (7) | −0.0021 (5) |
| C27 | 0.0274 (7) | 0.0302 (7) | 0.0207 (7) | −0.0135 (6) | 0.0075 (6) | −0.0090 (6) |
| C28 | 0.0206 (6) | 0.0297 (7) | 0.0189 (7) | −0.0126 (6) | 0.0019 (5) | −0.0082 (5) |
Geometric parameters (Å, °)
| Ni1—O1i | 1.9001 (9) | C9—H9A | 0.9900 |
| Ni1—O1 | 1.9001 (9) | C9—H9B | 0.9900 |
| Ni1—N1i | 2.0077 (10) | C10—H10A | 0.9900 |
| Ni1—N1 | 2.0077 (10) | C10—H10B | 0.9900 |
| Ni2—O4ii | 1.8873 (9) | C11—C12 | 1.5136 (18) |
| Ni2—O4 | 1.8873 (9) | C11—H11A | 0.9900 |
| Ni2—N3ii | 2.0105 (10) | C11—H11B | 0.9900 |
| Ni2—N3 | 2.0105 (10) | C12—H12A | 0.9900 |
| O1—C1 | 1.3052 (15) | C12—H12B | 0.9900 |
| O2—C3 | 1.3627 (16) | C13—C14 | 1.5180 (18) |
| O2—C7 | 1.4319 (16) | C13—H13A | 0.9900 |
| O3—C12 | 1.4237 (16) | C13—H13B | 0.9900 |
| O3—C13 | 1.4312 (16) | C14—H14A | 0.9900 |
| O4—C15 | 1.3048 (15) | C14—H14B | 0.9900 |
| O5—C17 | 1.3613 (16) | C15—C16 | 1.4140 (18) |
| O5—C21 | 1.4360 (15) | C15—C20 | 1.4225 (16) |
| O6—C26 | 1.419 (2) | C16—C17 | 1.3829 (17) |
| O6—C27 | 1.4244 (17) | C16—H16 | 0.9500 |
| N1—C8 | 1.2928 (17) | C17—C18 | 1.4149 (17) |
| N1—C9 | 1.4786 (15) | C18—C19 | 1.3697 (18) |
| N2—C11 | 1.4633 (16) | C18—H18 | 0.9500 |
| N2—C10 | 1.4650 (16) | C19—C20 | 1.4141 (17) |
| N2—C14 | 1.4700 (16) | C19—H19 | 0.9500 |
| N3—C22 | 1.2974 (16) | C20—C22 | 1.4281 (18) |
| N3—C23 | 1.4740 (16) | C21—H21A | 0.9800 |
| N4—C24 | 1.4614 (17) | C21—H21B | 0.9800 |
| N4—C28 | 1.4631 (17) | C21—H21C | 0.9800 |
| N4—C25 | 1.4667 (16) | C22—H22 | 0.9500 |
| C1—C2 | 1.4201 (18) | C23—C24 | 1.5235 (18) |
| C1—C6 | 1.4223 (17) | C23—H23A | 0.9900 |
| C2—C3 | 1.3830 (18) | C23—H23B | 0.9900 |
| C2—H2 | 0.9500 | C24—H24A | 0.9900 |
| C3—C4 | 1.4129 (18) | C24—H24B | 0.9900 |
| C4—C5 | 1.3698 (19) | C25—C26 | 1.512 (2) |
| C4—H4 | 0.9500 | C25—H25A | 0.9900 |
| C5—C6 | 1.4146 (17) | C25—H25B | 0.9900 |
| C5—H5 | 0.9500 | C26—H26A | 0.9900 |
| C6—C8 | 1.4270 (18) | C26—H26B | 0.9900 |
| C7—H7A | 0.9800 | C27—C28 | 1.5109 (19) |
| C7—H7B | 0.9800 | C27—H27A | 0.9900 |
| C7—H7C | 0.9800 | C27—H27B | 0.9900 |
| C8—H8 | 0.9500 | C28—H28A | 0.9900 |
| C9—C10 | 1.5197 (18) | C28—H28B | 0.9900 |
| O1i—Ni1—O1 | 180.00 (5) | O3—C12—H12B | 109.3 |
| O1i—Ni1—N1i | 91.36 (4) | C11—C12—H12B | 109.3 |
| O1—Ni1—N1i | 88.64 (4) | H12A—C12—H12B | 108.0 |
| O1i—Ni1—N1 | 88.64 (4) | O3—C13—C14 | 111.45 (11) |
| O1—Ni1—N1 | 91.36 (4) | O3—C13—H13A | 109.3 |
| N1i—Ni1—N1 | 180.000 (1) | C14—C13—H13A | 109.3 |
| O4ii—Ni2—O4 | 180.000 (1) | O3—C13—H13B | 109.3 |
| O4ii—Ni2—N3ii | 91.43 (4) | C14—C13—H13B | 109.3 |
| O4—Ni2—N3ii | 88.57 (4) | H13A—C13—H13B | 108.0 |
| O4ii—Ni2—N3 | 88.57 (4) | N2—C14—C13 | 110.41 (10) |
| O4—Ni2—N3 | 91.43 (4) | N2—C14—H14A | 109.6 |
| N3ii—Ni2—N3 | 180.00 (8) | C13—C14—H14A | 109.6 |
| C1—O1—Ni1 | 129.48 (8) | N2—C14—H14B | 109.6 |
| C3—O2—C7 | 117.40 (10) | C13—C14—H14B | 109.6 |
| C12—O3—C13 | 109.77 (10) | H14A—C14—H14B | 108.1 |
| C15—O4—Ni2 | 131.19 (8) | O4—C15—C16 | 117.97 (11) |
| C17—O5—C21 | 117.05 (10) | O4—C15—C20 | 123.00 (12) |
| C26—O6—C27 | 108.78 (11) | C16—C15—C20 | 119.02 (11) |
| C8—N1—C9 | 115.10 (10) | C17—C16—C15 | 120.42 (11) |
| C8—N1—Ni1 | 123.43 (9) | C17—C16—H16 | 119.8 |
| C9—N1—Ni1 | 121.41 (8) | C15—C16—H16 | 119.8 |
| C11—N2—C10 | 110.51 (10) | O5—C17—C16 | 124.33 (11) |
| C11—N2—C14 | 108.13 (10) | O5—C17—C18 | 114.78 (11) |
| C10—N2—C14 | 112.35 (10) | C16—C17—C18 | 120.89 (12) |
| C22—N3—C23 | 115.73 (10) | C19—C18—C17 | 118.91 (11) |
| C22—N3—Ni2 | 124.12 (9) | C19—C18—H18 | 120.5 |
| C23—N3—Ni2 | 120.03 (8) | C17—C18—H18 | 120.5 |
| C24—N4—C28 | 109.14 (10) | C18—C19—C20 | 122.07 (11) |
| C24—N4—C25 | 111.97 (10) | C18—C19—H19 | 119.0 |
| C28—N4—C25 | 109.90 (11) | C20—C19—H19 | 119.0 |
| O1—C1—C2 | 118.41 (11) | C19—C20—C15 | 118.67 (12) |
| O1—C1—C6 | 123.26 (12) | C19—C20—C22 | 118.84 (11) |
| C2—C1—C6 | 118.33 (12) | C15—C20—C22 | 122.41 (11) |
| C3—C2—C1 | 120.54 (12) | O5—C21—H21A | 109.5 |
| C3—C2—H2 | 119.7 | O5—C21—H21B | 109.5 |
| C1—C2—H2 | 119.7 | H21A—C21—H21B | 109.5 |
| O2—C3—C2 | 124.17 (11) | O5—C21—H21C | 109.5 |
| O2—C3—C4 | 114.60 (12) | H21A—C21—H21C | 109.5 |
| C2—C3—C4 | 121.22 (12) | H21B—C21—H21C | 109.5 |
| C5—C4—C3 | 118.52 (12) | N3—C22—C20 | 127.44 (11) |
| C5—C4—H4 | 120.7 | N3—C22—H22 | 116.3 |
| C3—C4—H4 | 120.7 | C20—C22—H22 | 116.3 |
| C4—C5—C6 | 122.20 (12) | N3—C23—C24 | 111.20 (10) |
| C4—C5—H5 | 118.9 | N3—C23—H23A | 109.4 |
| C6—C5—H5 | 118.9 | C24—C23—H23A | 109.4 |
| C5—C6—C1 | 119.11 (12) | N3—C23—H23B | 109.4 |
| C5—C6—C8 | 118.53 (11) | C24—C23—H23B | 109.4 |
| C1—C6—C8 | 122.35 (12) | H23A—C23—H23B | 108.0 |
| O2—C7—H7A | 109.5 | N4—C24—C23 | 111.74 (11) |
| O2—C7—H7B | 109.5 | N4—C24—H24A | 109.3 |
| H7A—C7—H7B | 109.5 | C23—C24—H24A | 109.3 |
| O2—C7—H7C | 109.5 | N4—C24—H24B | 109.3 |
| H7A—C7—H7C | 109.5 | C23—C24—H24B | 109.3 |
| H7B—C7—H7C | 109.5 | H24A—C24—H24B | 107.9 |
| N1—C8—C6 | 127.62 (11) | N4—C25—C26 | 109.78 (11) |
| N1—C8—H8 | 116.2 | N4—C25—H25A | 109.7 |
| C6—C8—H8 | 116.2 | C26—C25—H25A | 109.7 |
| N1—C9—C10 | 110.54 (10) | N4—C25—H25B | 109.7 |
| N1—C9—H9A | 109.5 | C26—C25—H25B | 109.7 |
| C10—C9—H9A | 109.5 | H25A—C25—H25B | 108.2 |
| N1—C9—H9B | 109.5 | O6—C26—C25 | 111.08 (14) |
| C10—C9—H9B | 109.5 | O6—C26—H26A | 109.4 |
| H9A—C9—H9B | 108.1 | C25—C26—H26A | 109.4 |
| N2—C10—C9 | 111.81 (10) | O6—C26—H26B | 109.4 |
| N2—C10—H10A | 109.3 | C25—C26—H26B | 109.4 |
| C9—C10—H10A | 109.3 | H26A—C26—H26B | 108.0 |
| N2—C10—H10B | 109.3 | O6—C27—C28 | 111.46 (12) |
| C9—C10—H10B | 109.3 | O6—C27—H27A | 109.3 |
| H10A—C10—H10B | 107.9 | C28—C27—H27A | 109.3 |
| N2—C11—C12 | 109.55 (11) | O6—C27—H27B | 109.3 |
| N2—C11—H11A | 109.8 | C28—C27—H27B | 109.3 |
| C12—C11—H11A | 109.8 | H27A—C27—H27B | 108.0 |
| N2—C11—H11B | 109.8 | N4—C28—C27 | 111.16 (12) |
| C12—C11—H11B | 109.8 | N4—C28—H28A | 109.4 |
| H11A—C11—H11B | 108.2 | C27—C28—H28A | 109.4 |
| O3—C12—C11 | 111.61 (10) | N4—C28—H28B | 109.4 |
| O3—C12—H12A | 109.3 | C27—C28—H28B | 109.4 |
| C11—C12—H12A | 109.3 | H28A—C28—H28B | 108.0 |
| N1i—Ni1—O1—C1 | −162.51 (11) | C13—O3—C12—C11 | 58.29 (14) |
| N1—Ni1—O1—C1 | 17.49 (11) | N2—C11—C12—O3 | −60.30 (15) |
| N3ii—Ni2—O4—C15 | 173.30 (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—C8 | 166.44 (11) | C10—N2—C14—C13 | 179.90 (11) |
| O1—Ni1—N1—C8 | −13.56 (11) | O3—C13—C14—N2 | 57.68 (15) |
| O1i—Ni1—N1—C9 | −10.58 (9) | Ni2—O4—C15—C16 | −170.87 (9) |
| O1—Ni1—N1—C9 | 169.42 (9) | Ni2—O4—C15—C20 | 8.59 (19) |
| O4ii—Ni2—N3—C22 | −177.97 (11) | O4—C15—C16—C17 | −179.89 (11) |
| O4—Ni2—N3—C22 | 2.03 (11) | C20—C15—C16—C17 | 0.63 (18) |
| O4ii—Ni2—N3—C23 | −2.22 (9) | C21—O5—C17—C16 | 8.00 (18) |
| O4—Ni2—N3—C23 | 177.78 (9) | C21—O5—C17—C18 | −171.33 (11) |
| Ni1—O1—C1—C2 | 166.26 (9) | C15—C16—C17—O5 | −178.45 (12) |
| Ni1—O1—C1—C6 | −12.93 (19) | C15—C16—C17—C18 | 0.85 (19) |
| O1—C1—C2—C3 | −177.25 (12) | O5—C17—C18—C19 | 177.94 (12) |
| C6—C1—C2—C3 | 1.99 (18) | C16—C17—C18—C19 | −1.43 (19) |
| C7—O2—C3—C2 | −6.01 (18) | C17—C18—C19—C20 | 0.51 (19) |
| C7—O2—C3—C4 | 174.14 (11) | C18—C19—C20—C15 | 0.94 (19) |
| C1—C2—C3—O2 | 176.76 (11) | C18—C19—C20—C22 | −175.93 (12) |
| C1—C2—C3—C4 | −3.39 (19) | O4—C15—C20—C19 | 179.04 (12) |
| O2—C3—C4—C5 | −177.91 (11) | C16—C15—C20—C19 | −1.50 (18) |
| C2—C3—C4—C5 | 2.23 (19) | O4—C15—C20—C22 | −4.20 (19) |
| C3—C4—C5—C6 | 0.3 (2) | C16—C15—C20—C22 | 175.25 (12) |
| C4—C5—C6—C1 | −1.59 (19) | C23—N3—C22—C20 | −175.40 (12) |
| C4—C5—C6—C8 | 179.30 (12) | Ni2—N3—C22—C20 | 0.52 (19) |
| O1—C1—C6—C5 | 179.65 (12) | C19—C20—C22—N3 | 176.48 (12) |
| C2—C1—C6—C5 | 0.45 (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—C8 | 179.52 (11) | Ni2—N3—C23—C24 | 75.15 (12) |
| C9—N1—C8—C6 | −176.67 (12) | C28—N4—C24—C23 | 171.84 (10) |
| Ni1—N1—C8—C6 | 6.13 (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—N1 | 4.2 (2) | C24—N4—C25—C26 | −176.26 (12) |
| C8—N1—C9—C10 | 101.55 (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—C9 | 167.06 (10) | N4—C25—C26—O6 | 60.01 (17) |
| C14—N2—C10—C9 | −72.06 (13) | C26—O6—C27—C28 | 59.59 (16) |
| N1—C9—C10—N2 | −175.82 (10) | C24—N4—C28—C27 | 176.61 (11) |
| C10—N2—C11—C12 | −177.93 (10) | C25—N4—C28—C27 | 53.46 (15) |
| C14—N2—C11—C12 | 58.71 (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. [DOI] [PMC free article] [PubMed]
- Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Westrip, S. P. (2009). publCIF In preparation.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020790/xu2537sup1.cif
e-65-0m733-sup1.cif (26.3KB, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020790/xu2537Isup2.hkl
e-65-0m733-Isup2.hkl (292.6KB, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report