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

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

doi:10.1107/S1600536809020790

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m733

doi:10.1107/S1600536809020790

Open

access

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

Nooraziah Mohd Lair,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^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 Ni^II 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, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.079
S = 1.02
5978 reflections
357 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −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 ); 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 ).

Supporting information

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

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

checkCIF report

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.

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

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
M_r = 585.33	F(000) = 620
Triclinic, P1	D_x = 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 top

Bruker SMART APEX diffractometer	5978 independent reflections
Radiation source: fine-focus sealed tube	5388 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.724, T_max = 0.831	k = −13→13
10299 measured reflections	l = −19→18

Refinement top

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(F_o²) + (0.0486P)² + 0.3802P] where P = (F_o² + 2F_c²)/3
5978 reflections	(Δ/σ)_max = 0.001
357 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Ni(C₁₄H₁₉N₂O₃)₂]	γ = 61.926 (1)°
M_r = 585.33	V = 1349.45 (3) Å³
Triclinic, P1	Z = 2
a = 10.3358 (1) Å	Mo Kα radiation
b = 10.4502 (1) Å	µ = 0.77 mm⁻¹
c = 14.8764 (2) Å	T = 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)
T_min = 0.724, T_max = 0.831	R_int = 0.014
10299 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.02	Δρ_max = 0.24 e Å⁻³
5978 reflections	Δρ_min = −0.45 e Å⁻³
357 parameters

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

	x	y	z	U_iso*/U_eq
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) top

	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, º) top

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.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₁₉N₂O₃)₂]
M_r	585.33
Crystal system, space group	Triclinic, 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)
V (Å³)	1349.45 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.45 × 0.35 × 0.25

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.724, 0.831
No. of measured, independent and observed [I > 2σ(I)] reflections	10299, 5978, 5388
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.079, 1.02
No. of reflections	5978
No. of parameters	357
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—O1	1.9001 (9)	Ni2—O4	1.8873 (9)
Ni1—N1	2.0077 (10)	Ni2—N3	2.0105 (10)

Acknowledgements

We thank the University of Malaya for supporting this study.

References

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