Bis{N'-[1-(2-pyrid-yl)ethyl-idene-κN]benzohydrazidato-κN',O}nickel(II).

In the title complex, [Ni(C(14)H(12)N(3)O)(2)], the Ni(II) atom lies at the centre of a distorted octahedron formed by two tridentate hydrazone ligands. Inter-molecular 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 = 535.24

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.182

S = 1.04

3600 reflections

336 parameters

2 restraints

H-atom parameters constrained

Δρmax = 1.05 e Å−3

Δρmin = −0.89 e Å−3

Absolute structure: Flack (1983 ▶), 1156 Friedel pairs

Flack parameter: 0.00 (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 ▶).

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

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

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

[Ni(C14H12N3O)2]	F(000) = 1112
Mr = 535.24	Dx = 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

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

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(Fo2) + (0.1528P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3600 reflections	Δρmax = 1.05 e Å−3
336 parameters	Δρmin = −0.88 e Å−3
2 restraints	Absolute structure: Flack (1983), 1156 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (2)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .