Bis{N′-[1-(2-pyrid­yl)ethyl­idene-κN]benzohydrazidato-κ2N′,O}nickel(II)

Datta, A.; Chuang, N.-T.; Sie, M.-H.; Huang, J.-H.; Lee, H.M.

doi:10.1107/S1600536810007336

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m359

doi:10.1107/S1600536810007336

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Bis{N′-[1-(2-pyridyl)ethylidene-κN]benzohydrazidato-κ²N′,O}nickel(II)

Amitabha Datta,^a Nien-Tsu Chuang,^a Ming-Han Sie,^a Jui-Hsien Huang ^a and Hon Man Lee ^a ^*

^aDepartment of Chemistry, National Changhua University of Education, Changhua 50058, Taiwan
^*Correspondence e-mail: leehm@cc.ncue.edu.tw

(Received 23 February 2010; accepted 26 February 2010; online 3 March 2010)

In the title complex, [Ni(C₁₄H₁₂N₃O)₂], the Ni^II atom lies at the centre of a distorted octahedron formed by two tridentate hydrazone ligands. Intermolecular hydrogen bonds of the type C—H⋯X (X = N, O) link the complexes into a two-dimensional network.

Related literature

For the preparation of the precursor ligand, see: Sen et al. (2005 ). For related complexes of the same ligand, see: Sen et al. (2005, 2007a ,b ), Ray et al. (2008 ).

Experimental

Crystal data

[Ni(C₁₄H₁₂N₃O)₂]
M_r = 535.24
Monoclinic, C c
a = 10.248 (6) Å
b = 19.692 (11) Å
c = 12.281 (7) Å
β = 91.523 (10)°
V = 2477 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 298 K
0.37 × 0.33 × 0.25 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.751, T_max = 0.821
5679 measured reflections
3600 independent reflections
3352 reflections with I > 2σ
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.182
S = 1.04
3600 reflections
336 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.89 e Å⁻³
Absolute structure: Flack (1983 ), 1156 Friedel pairs
Flack parameter: 0.00 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21B⋯N6	0.96	2.51	2.861 (10)	102
C10—H10⋯N3	0.93	2.51	2.813 (10)	100
C4—H4⋯O1ⁱ	0.93	2.51	3.164 (8)	128
C18—H18⋯O2ⁱⁱ	0.93	2.39	3.300 (9)	167
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: DIAMOND (Brandenburg, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007336/jh2131sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007336/jh2131Isup2.hkl

checkCIF report

Comment top

The title complex adopts a distorted octahedron geometry with two tridentate hydrazone ligands. While the N–Ni–N angle is 174.5 (2)°, which is close to the ideal 180°, the two O–Ni–N angles are much smaller (154.7 (2)° and 153.9 (2)°).

An intramolecular non-classical hydrogen bond of the type C—H···N is present. Non-classical intermolecular hydrogen bonds of type C—H···N and C—H···O also link complexes into a two-dimensional network.

Copper (Sen et al. 2007a)(Sen et al. 2007b), cadmium (Sen et al. 2005), zinc (Ray et al. 2008) and manganese (Ray et al. 2008) complexes of the same ligand have been published.

Related literature top

For the preparation of the precursor ligand, see: Sen et al. (2005). For related complexes of the same ligand, see: Sen et al. (2005, 2007a,b), Ray et al. (2008).

Experimental top

The ligand precursor, [C₆H₅C(O)NHN=C(CH₃)C₅H₄N] (LH) was prepared according to a literature procedure (Sen et al. 2005). To a methanolic solution (20 ml) of nickel chloride hexahydrate (0.237 g, 1.0 mmol), LH (0.478 g, 2 mmol) was added and then kept at room temperature. After a few days, dark brown, rectangular crystals of the title compound suitable for X-ray diffraction studies were formed. Crystals were collected and dried in the air. Yield: 0.147 g, 62%.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: DIAMOND (Brandenburg, 1999).

Figures top

	Fig. 1. The structure of the title complex, showing 50% displacement ellipsoids for non-H atoms. H atoms are excluded for clarity.
	Fig. 2. A packing diagram of the title compound along the c-axis showing the intermolecular hydrogen bonds (dashed lines).

Bis{N'-[1-(2-pyridyl)ethylidene-κN]benzohydrazidato- κ²N',O}nickel(II) top

Crystal data top

[Ni(C₁₄H₁₂N₃O)₂]	F(000) = 1112
M_r = 535.24	D_x = 1.435 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3920 reflections
a = 10.248 (6) Å	θ = 2.2–26.3°
b = 19.692 (11) Å	µ = 0.82 mm⁻¹
c = 12.281 (7) Å	T = 298 K
β = 91.523 (10)°	Parallelepiped, brown
V = 2477 (2) Å³	0.37 × 0.33 × 0.25 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	3600 independent reflections
Radiation source: fine-focus sealed tube	3352 reflections with I > 2σ
Graphite monochromator	R_int = 0.093
ω scans	θ_max = 26.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→10
T_min = 0.751, T_max = 0.821	k = −22→24
5679 measured reflections	l = −15→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.182	w = 1/[σ²(F_o²) + (0.1528P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3600 reflections	Δρ_max = 1.05 e Å⁻³
336 parameters	Δρ_min = −0.89 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1156 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

Crystal data top

[Ni(C₁₄H₁₂N₃O)₂]	V = 2477 (2) Å³
M_r = 535.24	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 10.248 (6) Å	µ = 0.82 mm⁻¹
b = 19.692 (11) Å	T = 298 K
c = 12.281 (7) Å	0.37 × 0.33 × 0.25 mm
β = 91.523 (10)°

Data collection top

Bruker SMART APEXII diffractometer	3600 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3352 reflections with I > 2σ
T_min = 0.751, T_max = 0.821	R_int = 0.093
5679 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.182	Δρ_max = 1.05 e Å⁻³
S = 1.04	Δρ_min = −0.89 e Å⁻³
3600 reflections	Absolute structure: Flack (1983), 1156 Friedel pairs
336 parameters	Absolute structure parameter: 0.00 (2)
2 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	1.1923 (7)	0.6618 (3)	0.3808 (6)	0.0451 (14)
H1	1.1942	0.6524	0.4550	0.054*
C2	1.2836 (8)	0.6300 (4)	0.3159 (7)	0.0561 (18)
H2	1.3456	0.6005	0.3460	0.067*
C3	1.2791 (7)	0.6435 (4)	0.2071 (7)	0.0552 (18)
H3	1.3385	0.6229	0.1616	0.066*
C4	1.1860 (7)	0.6880 (4)	0.1640 (6)	0.0467 (15)
H4	1.1812	0.6968	0.0896	0.056*
C5	1.0994 (6)	0.7192 (3)	0.2350 (5)	0.0370 (12)
C6	1.0010 (7)	0.7708 (3)	0.1986 (5)	0.0404 (14)
C7	0.9737 (8)	0.7881 (4)	0.0812 (5)	0.0532 (17)
H7A	0.9677	0.8365	0.0731	0.080*
H7B	0.8929	0.7676	0.0575	0.080*
H7C	1.0432	0.7712	0.0378	0.080*
C8	0.8049 (6)	0.8668 (3)	0.3545 (5)	0.0364 (12)
C9	0.7033 (7)	0.9222 (3)	0.3491 (5)	0.0400 (13)
C10	0.6377 (9)	0.9389 (4)	0.2532 (7)	0.064 (2)
H10	0.6593	0.9167	0.1893	0.076*
C11	0.5411 (9)	0.9875 (4)	0.2496 (7)	0.067 (2)
H11	0.4971	0.9973	0.1843	0.080*
C12	0.5094 (8)	1.0221 (4)	0.3453 (7)	0.0556 (18)
H12	0.4448	1.0553	0.3439	0.067*
C13	0.5742 (8)	1.0065 (3)	0.4398 (6)	0.0487 (16)
H13	0.5536	1.0294	0.5033	0.058*
C14	0.6709 (7)	0.9568 (3)	0.4436 (6)	0.0473 (15)
H14	0.7138	0.9466	0.5093	0.057*
C15	1.2059 (8)	0.8590 (4)	0.4491 (6)	0.0527 (17)
H15	1.1929	0.8680	0.3752	0.063*
C16	1.3118 (9)	0.8881 (4)	0.5021 (8)	0.063 (2)
H16	1.3707	0.9146	0.4646	0.076*
C17	1.3282 (8)	0.8767 (4)	0.6122 (8)	0.064 (2)
H17	1.3977	0.8967	0.6504	0.076*
C18	1.2418 (7)	0.8358 (3)	0.6658 (6)	0.0495 (16)
H18	1.2515	0.8283	0.7403	0.059*
C19	1.1398 (6)	0.8059 (3)	0.6063 (5)	0.0360 (12)
C20	1.0465 (7)	0.7564 (3)	0.6536 (5)	0.0374 (14)
C21	1.0476 (10)	0.7429 (4)	0.7719 (6)	0.0523 (19)
H21A	1.1219	0.7154	0.7914	0.078*
H21B	0.9691	0.7196	0.7903	0.078*
H21C	1.0528	0.7852	0.8108	0.078*
C22	0.8200 (6)	0.6570 (3)	0.5195 (5)	0.0358 (12)
C23	0.7290 (6)	0.6000 (3)	0.5351 (5)	0.0384 (12)
C24	0.7114 (8)	0.5723 (4)	0.6395 (6)	0.0568 (18)
H24	0.7605	0.5879	0.6992	0.068*
C25	0.6194 (10)	0.5212 (5)	0.6517 (9)	0.081 (3)
H25	0.6088	0.5021	0.7202	0.098*
C26	0.5425 (10)	0.4977 (5)	0.5641 (9)	0.075 (3)
H26	0.4785	0.4650	0.5743	0.090*
C27	0.5632 (8)	0.5235 (4)	0.4637 (8)	0.061 (2)
H27	0.5155	0.5067	0.4042	0.073*
C28	0.6546 (7)	0.5747 (3)	0.4480 (6)	0.0462 (14)
H28	0.6659	0.5921	0.3785	0.055*
N1	1.1029 (5)	0.7048 (3)	0.3422 (4)	0.0379 (11)
N2	0.9417 (5)	0.7980 (3)	0.2778 (4)	0.0338 (10)
N3	0.8495 (6)	0.8480 (3)	0.2592 (4)	0.0414 (11)
N4	1.1212 (5)	0.8188 (3)	0.4977 (4)	0.0389 (11)
N5	0.9746 (6)	0.7265 (2)	0.5806 (4)	0.0352 (11)
N6	0.8911 (5)	0.6760 (3)	0.6080 (4)	0.0373 (11)
Ni1	0.96750 (6)	0.76219 (3)	0.42846 (5)	0.0314 (2)
O1	0.8347 (5)	0.8422 (2)	0.4467 (4)	0.0439 (10)
O2	0.8288 (5)	0.6838 (2)	0.4245 (4)	0.0415 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.027 (3)	0.057 (3)	0.052 (4)	0.004 (3)	0.000 (3)	−0.001 (3)
C2	0.035 (4)	0.057 (4)	0.077 (6)	0.008 (3)	0.002 (3)	−0.007 (3)
C3	0.035 (4)	0.065 (4)	0.067 (5)	0.005 (3)	0.016 (3)	−0.016 (3)
C4	0.033 (4)	0.062 (4)	0.045 (4)	−0.004 (3)	0.012 (3)	−0.010 (3)
C5	0.027 (3)	0.049 (3)	0.035 (3)	−0.009 (3)	0.006 (2)	−0.004 (2)
C6	0.041 (4)	0.050 (3)	0.031 (3)	−0.012 (3)	0.007 (3)	0.001 (2)
C7	0.057 (5)	0.072 (4)	0.030 (3)	−0.007 (4)	0.004 (3)	0.005 (3)
C8	0.027 (3)	0.044 (3)	0.038 (3)	0.000 (2)	0.002 (2)	0.000 (2)
C9	0.035 (3)	0.047 (3)	0.038 (3)	−0.001 (3)	0.001 (2)	0.004 (2)
C10	0.068 (6)	0.068 (4)	0.055 (4)	0.027 (4)	−0.009 (4)	0.000 (3)
C11	0.070 (6)	0.067 (4)	0.062 (5)	0.031 (4)	−0.019 (4)	0.002 (4)
C12	0.042 (4)	0.057 (4)	0.069 (5)	0.010 (3)	0.006 (3)	0.009 (3)
C13	0.051 (4)	0.051 (3)	0.045 (4)	0.001 (3)	0.010 (3)	0.002 (3)
C14	0.042 (4)	0.053 (3)	0.047 (4)	−0.002 (3)	0.003 (3)	0.007 (3)
C15	0.052 (5)	0.057 (4)	0.049 (4)	−0.010 (3)	−0.006 (3)	0.006 (3)
C16	0.050 (5)	0.055 (4)	0.085 (6)	−0.018 (4)	−0.001 (4)	0.004 (4)
C17	0.046 (5)	0.057 (4)	0.086 (6)	−0.008 (3)	−0.023 (4)	−0.011 (4)
C18	0.045 (4)	0.050 (3)	0.053 (4)	0.005 (3)	−0.013 (3)	−0.017 (3)
C19	0.022 (3)	0.042 (3)	0.044 (3)	0.011 (2)	−0.003 (2)	−0.005 (2)
C20	0.039 (4)	0.042 (3)	0.031 (3)	0.007 (2)	−0.002 (3)	−0.003 (2)
C21	0.058 (6)	0.065 (4)	0.033 (4)	0.012 (3)	−0.009 (3)	0.000 (3)
C22	0.029 (3)	0.047 (3)	0.031 (3)	0.005 (2)	0.004 (2)	−0.002 (2)
C23	0.021 (3)	0.049 (3)	0.046 (3)	0.000 (2)	0.009 (2)	0.005 (2)
C24	0.054 (5)	0.066 (4)	0.051 (4)	−0.001 (4)	0.009 (3)	0.021 (3)
C25	0.079 (7)	0.088 (6)	0.079 (7)	−0.016 (5)	0.025 (6)	0.028 (5)
C26	0.056 (5)	0.067 (5)	0.103 (8)	−0.014 (4)	0.018 (5)	0.017 (5)
C27	0.044 (4)	0.056 (4)	0.083 (6)	−0.012 (3)	0.006 (4)	0.004 (4)
C28	0.031 (3)	0.051 (3)	0.057 (4)	−0.007 (3)	0.002 (3)	−0.001 (3)
N1	0.026 (3)	0.049 (3)	0.039 (3)	−0.004 (2)	0.002 (2)	−0.001 (2)
N2	0.021 (2)	0.053 (3)	0.027 (2)	−0.0020 (19)	0.0042 (17)	0.0075 (19)
N3	0.036 (3)	0.052 (3)	0.036 (3)	0.004 (2)	0.002 (2)	0.009 (2)
N4	0.024 (2)	0.046 (3)	0.047 (3)	−0.004 (2)	−0.002 (2)	−0.003 (2)
N5	0.030 (3)	0.048 (2)	0.028 (3)	0.008 (2)	0.002 (2)	−0.0004 (18)
N6	0.030 (3)	0.046 (2)	0.037 (3)	0.001 (2)	0.001 (2)	0.0061 (19)
Ni1	0.0219 (4)	0.0438 (3)	0.0284 (4)	−0.0005 (3)	0.0006 (2)	0.0020 (3)
O1	0.039 (3)	0.057 (2)	0.036 (2)	0.010 (2)	0.0046 (19)	0.0086 (18)
O2	0.036 (3)	0.056 (2)	0.032 (2)	−0.0078 (19)	−0.0022 (18)	0.0039 (17)

Geometric parameters (Å, º) top

C1—N1	1.326 (9)	C16—H16	0.9300
C1—C2	1.393 (10)	C17—C18	1.378 (12)
C1—H1	0.9300	C17—H17	0.9300
C2—C3	1.362 (12)	C18—C19	1.389 (9)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.391 (12)	C19—N4	1.366 (8)
C3—H3	0.9300	C19—C20	1.493 (9)
C4—C5	1.402 (9)	C20—N5	1.288 (9)
C4—H4	0.9300	C20—C21	1.477 (10)
C5—N1	1.346 (8)	C21—H21A	0.9600
C5—C6	1.492 (10)	C21—H21B	0.9600
C6—N2	1.277 (9)	C21—H21C	0.9600
C6—C7	1.501 (9)	C22—O2	1.285 (8)
C7—H7A	0.9600	C22—N6	1.346 (8)
C7—H7B	0.9600	C22—C23	1.476 (9)
C7—H7C	0.9600	C23—C28	1.389 (10)
C8—O1	1.262 (8)	C23—C24	1.410 (9)
C8—N3	1.321 (8)	C24—C25	1.390 (12)
C8—C9	1.508 (9)	C24—H24	0.9300
C9—C10	1.381 (10)	C25—C26	1.396 (16)
C9—C14	1.393 (10)	C25—H25	0.9300
C10—C11	1.376 (11)	C26—C27	1.355 (13)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.404 (12)	C27—C28	1.394 (10)
C11—H11	0.9300	C27—H27	0.9300
C12—C13	1.358 (11)	C28—H28	0.9300
C12—H12	0.9300	N1—Ni1	2.099 (5)
C13—C14	1.393 (10)	N2—N3	1.380 (8)
C13—H13	0.9300	N2—Ni1	1.992 (5)
C14—H14	0.9300	N4—Ni1	2.091 (5)
C15—N4	1.329 (9)	N5—N6	1.359 (8)
C15—C16	1.375 (12)	N5—Ni1	1.995 (5)
C15—H15	0.9300	Ni1—O1	2.098 (5)
C16—C17	1.376 (12)	Ni1—O2	2.098 (5)

N1—C1—C2	123.4 (7)	N5—C20—C19	112.9 (6)
N1—C1—H1	118.3	C21—C20—C19	120.7 (6)
C2—C1—H1	118.3	C20—C21—H21A	109.5
C3—C2—C1	117.9 (7)	C20—C21—H21B	109.5
C3—C2—H2	121.1	H21A—C21—H21B	109.5
C1—C2—H2	121.1	C20—C21—H21C	109.5
C2—C3—C4	120.1 (6)	H21A—C21—H21C	109.5
C2—C3—H3	120.0	H21B—C21—H21C	109.5
C4—C3—H3	120.0	O2—C22—N6	124.7 (6)
C3—C4—C5	118.6 (7)	O2—C22—C23	119.3 (5)
C3—C4—H4	120.7	N6—C22—C23	116.0 (5)
C5—C4—H4	120.7	C28—C23—C24	118.7 (7)
N1—C5—C4	121.0 (6)	C28—C23—C22	120.6 (6)
N1—C5—C6	115.9 (5)	C24—C23—C22	120.6 (6)
C4—C5—C6	123.1 (6)	C25—C24—C23	118.8 (9)
N2—C6—C5	112.9 (6)	C25—C24—H24	120.6
N2—C6—C7	123.8 (7)	C23—C24—H24	120.6
C5—C6—C7	123.3 (6)	C24—C25—C26	121.8 (8)
C6—C7—H7A	109.5	C24—C25—H25	119.1
C6—C7—H7B	109.5	C26—C25—H25	119.1
H7A—C7—H7B	109.5	C27—C26—C25	118.6 (8)
C6—C7—H7C	109.5	C27—C26—H26	120.7
H7A—C7—H7C	109.5	C25—C26—H26	120.7
H7B—C7—H7C	109.5	C26—C27—C28	121.3 (9)
O1—C8—N3	127.4 (6)	C26—C27—H27	119.3
O1—C8—C9	117.8 (5)	C28—C27—H27	119.3
N3—C8—C9	114.7 (5)	C23—C28—C27	120.7 (7)
C10—C9—C14	118.2 (7)	C23—C28—H28	119.7
C10—C9—C8	122.0 (6)	C27—C28—H28	119.7
C14—C9—C8	119.8 (6)	C1—N1—C5	119.0 (6)
C11—C10—C9	121.8 (8)	C1—N1—Ni1	128.6 (5)
C11—C10—H10	119.1	C5—N1—Ni1	112.3 (4)
C9—C10—H10	119.1	C6—N2—N3	120.7 (5)
C10—C11—C12	119.5 (7)	C6—N2—Ni1	120.3 (5)
C10—C11—H11	120.2	N3—N2—Ni1	118.7 (4)
C12—C11—H11	120.2	C8—N3—N2	107.7 (5)
C13—C12—C11	119.2 (7)	C15—N4—C19	118.3 (6)
C13—C12—H12	120.4	C15—N4—Ni1	129.0 (5)
C11—C12—H12	120.4	C19—N4—Ni1	112.5 (4)
C12—C13—C14	121.3 (7)	C20—N5—N6	120.9 (5)
C12—C13—H13	119.4	C20—N5—Ni1	119.7 (5)
C14—C13—H13	119.4	N6—N5—Ni1	118.8 (4)
C13—C14—C9	120.1 (7)	C22—N6—N5	109.5 (5)
C13—C14—H14	120.0	N2—Ni1—N5	174.5 (2)
C9—C14—H14	120.0	N2—Ni1—N4	105.6 (2)
N4—C15—C16	123.5 (7)	N5—Ni1—N4	78.4 (2)
N4—C15—H15	118.3	N2—Ni1—O1	76.29 (19)
C16—C15—H15	118.3	N5—Ni1—O1	99.93 (19)
C15—C16—C17	118.2 (7)	N4—Ni1—O1	92.3 (2)
C15—C16—H16	120.9	N2—Ni1—O2	99.56 (19)
C17—C16—H16	120.9	N5—Ni1—O2	76.7 (2)
C16—C17—C18	120.1 (7)	N4—Ni1—O2	154.7 (2)
C16—C17—H17	120.0	O1—Ni1—O2	96.6 (2)
C18—C17—H17	120.0	N2—Ni1—N1	78.2 (2)
C17—C18—C19	118.7 (7)	N5—Ni1—N1	105.9 (2)
C17—C18—H18	120.6	N4—Ni1—N1	89.5 (2)
C19—C18—H18	120.6	O1—Ni1—N1	153.90 (19)
N4—C19—C18	121.2 (6)	O2—Ni1—N1	92.8 (2)
N4—C19—C20	115.2 (5)	C8—O1—Ni1	109.5 (4)
C18—C19—C20	123.6 (6)	C22—O2—Ni1	110.1 (4)
N5—C20—C21	126.3 (7)

N1—C1—C2—C3	−0.8 (11)	C18—C19—N4—Ni1	176.5 (5)
C1—C2—C3—C4	0.3 (11)	C20—C19—N4—Ni1	−1.5 (6)
C2—C3—C4—C5	1.2 (11)	C21—C20—N5—N6	−1.5 (10)
C3—C4—C5—N1	−2.3 (10)	C19—C20—N5—N6	174.9 (5)
C3—C4—C5—C6	176.2 (6)	C21—C20—N5—Ni1	170.3 (6)
N1—C5—C6—N2	5.6 (8)	C19—C20—N5—Ni1	−13.3 (7)
C4—C5—C6—N2	−173.0 (6)	O2—C22—N6—N5	−1.3 (8)
N1—C5—C6—C7	−173.6 (6)	C23—C22—N6—N5	177.0 (5)
C4—C5—C6—C7	7.8 (10)	C20—N5—N6—C22	175.0 (6)
O1—C8—C9—C10	−161.4 (7)	Ni1—N5—N6—C22	3.1 (6)
N3—C8—C9—C10	16.3 (10)	C6—N2—Ni1—N4	92.0 (5)
O1—C8—C9—C14	16.8 (9)	N3—N2—Ni1—N4	−94.3 (4)
N3—C8—C9—C14	−165.5 (6)	C6—N2—Ni1—O1	−179.5 (5)
C14—C9—C10—C11	−1.0 (13)	N3—N2—Ni1—O1	−5.7 (4)
C8—C9—C10—C11	177.2 (8)	C6—N2—Ni1—O2	−85.0 (5)
C9—C10—C11—C12	1.2 (14)	N3—N2—Ni1—O2	88.7 (4)
C10—C11—C12—C13	−0.5 (13)	C6—N2—Ni1—N1	5.9 (5)
C11—C12—C13—C14	−0.2 (12)	N3—N2—Ni1—N1	179.6 (5)
C12—C13—C14—C9	0.3 (11)	C20—N5—Ni1—N4	10.0 (5)
C10—C9—C14—C13	0.3 (10)	N6—N5—Ni1—N4	−178.1 (4)
C8—C9—C14—C13	−178.0 (6)	C20—N5—Ni1—O1	−80.3 (5)
N4—C15—C16—C17	−2.3 (13)	N6—N5—Ni1—O1	91.6 (4)
C15—C16—C17—C18	1.7 (13)	C20—N5—Ni1—O2	−174.8 (5)
C16—C17—C18—C19	0.8 (11)	N6—N5—Ni1—O2	−2.8 (4)
C17—C18—C19—N4	−2.8 (9)	C20—N5—Ni1—N1	96.1 (5)
C17—C18—C19—C20	175.0 (6)	N6—N5—Ni1—N1	−91.9 (4)
N4—C19—C20—N5	9.3 (7)	C15—N4—Ni1—N2	−14.2 (7)
C18—C19—C20—N5	−168.7 (6)	C19—N4—Ni1—N2	172.2 (4)
N4—C19—C20—C21	−174.1 (6)	C15—N4—Ni1—N5	169.7 (7)
C18—C19—C20—C21	8.0 (9)	C19—N4—Ni1—N5	−3.8 (4)
O2—C22—C23—C28	0.9 (9)	C15—N4—Ni1—O1	−90.6 (6)
N6—C22—C23—C28	−177.6 (6)	C19—N4—Ni1—O1	95.8 (4)
O2—C22—C23—C24	−176.2 (6)	C15—N4—Ni1—O2	158.8 (6)
N6—C22—C23—C24	5.4 (9)	C19—N4—Ni1—O2	−14.7 (7)
C28—C23—C24—C25	−0.6 (11)	C15—N4—Ni1—N1	63.3 (6)
C22—C23—C24—C25	176.5 (7)	C19—N4—Ni1—N1	−110.2 (4)
C23—C24—C25—C26	−1.3 (14)	C1—N1—Ni1—N2	173.1 (6)
C24—C25—C26—C27	3.2 (16)	C5—N1—Ni1—N2	−2.1 (4)
C25—C26—C27—C28	−3.1 (14)	C1—N1—Ni1—N5	−10.8 (6)
C24—C23—C28—C27	0.8 (10)	C5—N1—Ni1—N5	174.0 (4)
C22—C23—C28—C27	−176.3 (6)	C1—N1—Ni1—N4	67.0 (6)
C26—C27—C28—C23	1.1 (12)	C5—N1—Ni1—N4	−108.2 (4)
C2—C1—N1—C5	−0.3 (10)	C1—N1—Ni1—O1	161.2 (5)
C2—C1—N1—Ni1	−175.2 (5)	C5—N1—Ni1—O1	−14.0 (7)
C4—C5—N1—C1	1.8 (9)	C1—N1—Ni1—O2	−87.8 (6)
C6—C5—N1—C1	−176.8 (6)	C5—N1—Ni1—O2	97.0 (4)
C4—C5—N1—Ni1	177.6 (5)	N3—C8—O1—Ni1	−1.3 (8)
C6—C5—N1—Ni1	−1.0 (6)	C9—C8—O1—Ni1	176.1 (4)
C5—C6—N2—N3	178.5 (5)	N2—Ni1—O1—C8	3.6 (4)
C7—C6—N2—N3	−2.3 (10)	N5—Ni1—O1—C8	−172.2 (4)
C5—C6—N2—Ni1	−7.9 (7)	N4—Ni1—O1—C8	109.1 (4)
C7—C6—N2—Ni1	171.3 (5)	O2—Ni1—O1—C8	−94.6 (4)
O1—C8—N3—N2	−3.2 (9)	N1—Ni1—O1—C8	15.6 (7)
C9—C8—N3—N2	179.4 (5)	N6—C22—O2—Ni1	−0.9 (7)
C6—N2—N3—C8	−179.8 (6)	C23—C22—O2—Ni1	−179.2 (4)
Ni1—N2—N3—C8	6.5 (7)	N2—Ni1—O2—C22	−173.9 (4)
C16—C15—N4—C19	0.4 (11)	N5—Ni1—O2—C22	1.9 (4)
C16—C15—N4—Ni1	−172.8 (6)	N4—Ni1—O2—C22	12.9 (7)
C18—C19—N4—C15	2.2 (9)	O1—Ni1—O2—C22	−96.8 (4)
C20—C19—N4—C15	−175.8 (6)	N1—Ni1—O2—C22	107.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···N6	0.96	2.51	2.861 (10)	102
C10—H10···N3	0.93	2.51	2.813 (10)	100
C4—H4···O1ⁱ	0.93	2.51	3.164 (8)	128
C18—H18···O2ⁱⁱ	0.93	2.39	3.300 (9)	167

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₁₂N₃O)₂]
M_r	535.24
Crystal system, space group	Monoclinic, Cc
Temperature (K)	298
a, b, c (Å)	10.248 (6), 19.692 (11), 12.281 (7)
β (°)	91.523 (10)
V (Å³)	2477 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.37 × 0.33 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.751, 0.821
No. of measured, independent and observed (I > 2σ) reflections	5679, 3600, 3352
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.182, 1.04
No. of reflections	3600
No. of parameters	336
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.89
Absolute structure	Flack (1983), 1156 Friedel pairs
Absolute structure parameter	0.00 (2)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···N6	0.96	2.51	2.861 (10)	102
C10—H10···N3	0.93	2.51	2.813 (10)	100
C4—H4···O1ⁱ	0.93	2.51	3.164 (8)	128
C18—H18···O2ⁱⁱ	0.93	2.39	3.300 (9)	167

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x+1/2, −y+3/2, z+1/2.

Acknowledgements

We are grateful to the National Science Council of Taiwan for financial support.

References

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