Bis(dimethyl-formamide-κO){4,4',6,6'-tetra-chloro-2,2-[butane-1,4-di-yl(nitrilo-methanylyl-idene)]diphenolato-κ(4)O,N,N',O'}nickel(II).

In the title Schiff base complex, [Ni(C(18)H(14)Cl(4)N(2)O(2))(C(3)H(7)NO)(2)], the geometry around the Ni(II) atom is distorted octa-hedral. It is coordinated by the N(2)O(2) donor atoms of the tetra-dentate Schiff base ligand and the O atoms of two dimethyl-formamide mol-ecules, which are cis to one another. The benzene rings are almost normal to each other [dihedral angle = 88.60 (14)°]. The various intra-molecular C-H⋯O hydrogen bonds make S(5) and S(6) ring motifs. In the crystal, mol-ecules are linked by pairs of weak C-H⋯Cl inter-actions, forming inversion dimers.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to Schiff base ligands and their complexes, see: Kargar, Kia, Abbasian et al. (2012 ▶); Kargar et al. (2011 ▶); Kia et al. (2010 ▶). For the crystal structure of the ligand, see: Kargar, Kia, Ardakani et al. (2012 ▶).

Experimental

Crystal data

[Ni(C18H14Cl4N2O2)(C3H7NO)2]

M = 637.01

Monoclinic,

a = 9.7392 (11) Å

b = 19.165 (2) Å

c = 15.0197 (14) Å

β = 93.236 (3)°

V = 2799.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.11 mm−1

T = 291 K

0.36 × 0.28 × 0.26 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.690, T max = 0.761

23789 measured reflections

6633 independent reflections

4349 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.02

6633 reflections

338 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028681/su2463sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028681/su2463Isup2.hkl

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

[Ni(C18H14Cl4N2O2)(C3H7NO)2]	F(000) = 1312
Mr = 637.01	Dx = 1.512 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3422 reflections
a = 9.7392 (11) Å	θ = 2.8–27.5°
b = 19.165 (2) Å	µ = 1.11 mm−1
c = 15.0197 (14) Å	T = 291 K
β = 93.236 (3)°	Prism, green
V = 2799.0 (5) Å3	0.36 × 0.28 × 0.26 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6633 independent reflections
Radiation source: fine-focus sealed tube	4349 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 27.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.690, Tmax = 0.761	k = −25→25
23789 measured reflections	l = −18→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.7005P] where P = (Fo2 + 2Fc2)/3
6633 reflections	(Δ/σ)max = 0.001
338 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Ni1	0.03675 (3)	0.167782 (17)	0.39862 (2)	0.03835 (12)
Cl1	0.42524 (9)	0.25307 (4)	0.57798 (6)	0.0652 (2)
Cl2	0.34269 (10)	0.05880 (5)	0.83006 (6)	0.0714 (3)
Cl3	0.40497 (8)	0.00038 (5)	0.36167 (6)	0.0626 (2)
Cl4	0.18116 (14)	−0.08010 (6)	0.04365 (7)	0.0929 (4)
O1	0.1739 (2)	0.19835 (9)	0.49423 (13)	0.0440 (5)
O2	0.1643 (2)	0.09054 (10)	0.36689 (14)	0.0477 (5)
O3	0.1363 (2)	0.23648 (11)	0.31056 (15)	0.0545 (5)
O4	−0.0881 (2)	0.25534 (10)	0.43674 (16)	0.0536 (5)
N1	−0.0578 (2)	0.10534 (11)	0.48708 (16)	0.0393 (5)
N2	−0.0946 (2)	0.14157 (11)	0.29273 (16)	0.0413 (5)
N3	0.3381 (3)	0.28212 (13)	0.27093 (18)	0.0524 (6)
N4	−0.1082 (3)	0.34747 (13)	0.5284 (2)	0.0599 (7)
C1	0.2073 (3)	0.16609 (13)	0.56753 (19)	0.0375 (6)
C2	0.3275 (3)	0.18564 (14)	0.6196 (2)	0.0438 (7)
C3	0.3696 (3)	0.15504 (15)	0.6988 (2)	0.0507 (7)
H3	0.4488	0.1700	0.7307	0.061*
C4	0.2906 (3)	0.10097 (15)	0.7302 (2)	0.0477 (7)
C5	0.1725 (3)	0.08039 (14)	0.68435 (19)	0.0440 (7)
H5	0.1200	0.0449	0.7074	0.053*
C6	0.1289 (3)	0.11139 (13)	0.60378 (19)	0.0395 (6)
C7	0.0006 (3)	0.08645 (13)	0.5616 (2)	0.0425 (7)
H7	−0.0451	0.0524	0.5927	0.051*
C8	−0.1887 (3)	0.07074 (15)	0.4602 (2)	0.0499 (7)
H8A	−0.2166	0.0421	0.5093	0.060*
H8B	−0.1741	0.0400	0.4103	0.060*
C9	−0.3051 (3)	0.12120 (16)	0.4337 (2)	0.0539 (8)
H9A	−0.3881	0.1052	0.4601	0.065*
H9B	−0.2824	0.1666	0.4589	0.065*
C10	−0.3356 (3)	0.12976 (16)	0.3339 (2)	0.0535 (8)
H10A	−0.3411	0.0837	0.3071	0.064*
H10B	−0.4254	0.1513	0.3245	0.064*
C11	−0.2327 (3)	0.17269 (15)	0.2847 (2)	0.0485 (7)
H11A	−0.2630	0.1758	0.2222	0.058*
H11B	−0.2290	0.2196	0.3090	0.058*
C12	−0.0633 (3)	0.10065 (14)	0.22963 (19)	0.0416 (6)
H12	−0.1270	0.0977	0.1813	0.050*
C13	0.0590 (3)	0.05857 (14)	0.22437 (19)	0.0424 (7)
C14	0.0659 (3)	0.01658 (16)	0.1478 (2)	0.0510 (7)
H14	−0.0042	0.0189	0.1032	0.061*
C15	0.1742 (4)	−0.02746 (16)	0.1383 (2)	0.0556 (8)
C16	0.2789 (3)	−0.03246 (15)	0.2039 (2)	0.0540 (8)
H16	0.3522	−0.0628	0.1972	0.065*
C17	0.2736 (3)	0.00781 (14)	0.2790 (2)	0.0447 (7)
C18	0.1638 (3)	0.05554 (14)	0.2943 (2)	0.0411 (6)
C19	0.2586 (3)	0.24959 (15)	0.3267 (2)	0.0493 (7)
H19	0.2982	0.2358	0.3817	0.059*
C20	0.2846 (4)	0.30430 (19)	0.1833 (2)	0.0675 (10)
H20A	0.1949	0.2845	0.1712	0.101*
H20B	0.3450	0.2887	0.1391	0.101*
H20C	0.2783	0.3543	0.1818	0.101*
C21	0.4789 (4)	0.3010 (2)	0.2978 (3)	0.0774 (11)
H21A	0.5021	0.2828	0.3563	0.116*
H21B	0.4875	0.3509	0.2987	0.116*
H21C	0.5400	0.2818	0.2562	0.116*
C22	−0.0370 (3)	0.30254 (15)	0.4834 (2)	0.0518 (8)
H22	0.0583	0.3067	0.4872	0.062*
C23	−0.2567 (4)	0.3464 (2)	0.5240 (3)	0.0882 (14)
H23A	−0.2892	0.3089	0.4859	0.132*
H23B	−0.2912	0.3899	0.5003	0.132*
H23C	−0.2885	0.3396	0.5827	0.132*
C24	−0.0397 (5)	0.4028 (2)	0.5811 (4)	0.1100 (18)
H24A	−0.0736	0.4474	0.5606	0.165*
H24B	0.0577	0.4005	0.5746	0.165*
H24C	−0.0583	0.3970	0.6428	0.165*

	U11	U22	U33	U12	U13	U23
Ni1	0.03646 (19)	0.03847 (19)	0.0406 (2)	−0.00509 (14)	0.00601 (15)	0.00000 (15)
Cl1	0.0587 (5)	0.0703 (5)	0.0656 (6)	−0.0261 (4)	−0.0058 (4)	0.0115 (4)
Cl2	0.0795 (6)	0.0831 (6)	0.0507 (5)	0.0078 (5)	−0.0038 (4)	0.0170 (4)
Cl3	0.0420 (4)	0.0766 (6)	0.0693 (6)	0.0060 (4)	0.0048 (4)	0.0036 (4)
Cl4	0.1229 (9)	0.0960 (8)	0.0603 (6)	0.0309 (7)	0.0097 (6)	−0.0273 (5)
O1	0.0462 (11)	0.0416 (10)	0.0439 (12)	−0.0094 (8)	0.0011 (9)	0.0038 (9)
O2	0.0433 (11)	0.0566 (12)	0.0432 (12)	0.0064 (9)	0.0019 (9)	−0.0071 (10)
O3	0.0435 (12)	0.0663 (13)	0.0537 (14)	−0.0126 (10)	0.0046 (10)	0.0147 (11)
O4	0.0486 (12)	0.0433 (11)	0.0691 (15)	−0.0007 (9)	0.0056 (11)	−0.0119 (10)
N1	0.0391 (12)	0.0368 (11)	0.0426 (15)	−0.0064 (9)	0.0079 (10)	−0.0031 (10)
N2	0.0363 (12)	0.0409 (12)	0.0466 (15)	−0.0010 (9)	0.0024 (10)	0.0035 (11)
N3	0.0482 (15)	0.0560 (15)	0.0540 (17)	−0.0036 (12)	0.0129 (12)	0.0131 (12)
N4	0.0649 (18)	0.0504 (15)	0.0648 (19)	0.0059 (13)	0.0066 (15)	−0.0137 (13)
C1	0.0394 (14)	0.0321 (12)	0.0416 (17)	0.0031 (11)	0.0080 (12)	−0.0032 (12)
C2	0.0434 (16)	0.0412 (14)	0.0471 (19)	−0.0034 (12)	0.0054 (13)	−0.0020 (13)
C3	0.0451 (16)	0.0573 (18)	0.049 (2)	0.0048 (14)	−0.0011 (14)	−0.0009 (15)
C4	0.0537 (18)	0.0508 (16)	0.0386 (18)	0.0111 (14)	0.0041 (14)	0.0046 (13)
C5	0.0542 (18)	0.0398 (14)	0.0393 (17)	0.0007 (12)	0.0138 (14)	−0.0016 (12)
C6	0.0453 (15)	0.0350 (13)	0.0394 (17)	0.0007 (11)	0.0123 (12)	−0.0021 (11)
C7	0.0463 (16)	0.0362 (14)	0.0468 (19)	−0.0054 (12)	0.0190 (14)	0.0010 (12)
C8	0.0482 (17)	0.0455 (16)	0.056 (2)	−0.0161 (13)	0.0061 (14)	0.0006 (14)
C9	0.0392 (16)	0.0607 (19)	0.063 (2)	−0.0134 (14)	0.0131 (14)	−0.0137 (15)
C10	0.0354 (15)	0.0563 (18)	0.069 (2)	−0.0025 (13)	0.0039 (14)	−0.0054 (16)
C11	0.0392 (15)	0.0496 (16)	0.056 (2)	0.0017 (12)	−0.0025 (14)	−0.0013 (14)
C12	0.0405 (15)	0.0442 (15)	0.0398 (17)	−0.0041 (12)	−0.0010 (12)	0.0014 (12)
C13	0.0447 (16)	0.0435 (15)	0.0396 (17)	−0.0009 (12)	0.0069 (13)	0.0062 (12)
C14	0.0596 (19)	0.0535 (18)	0.0401 (18)	−0.0003 (14)	0.0052 (14)	0.0011 (14)
C15	0.070 (2)	0.0538 (18)	0.0440 (19)	0.0072 (16)	0.0124 (17)	−0.0045 (15)
C16	0.0560 (19)	0.0482 (16)	0.060 (2)	0.0041 (14)	0.0239 (17)	0.0032 (15)
C17	0.0400 (15)	0.0465 (15)	0.0486 (18)	−0.0013 (12)	0.0109 (13)	0.0057 (13)
C18	0.0384 (14)	0.0417 (14)	0.0443 (18)	−0.0061 (11)	0.0125 (12)	0.0060 (13)
C19	0.0445 (17)	0.0552 (17)	0.0483 (19)	−0.0039 (13)	0.0056 (14)	0.0167 (14)
C20	0.075 (2)	0.075 (2)	0.054 (2)	−0.0091 (19)	0.0167 (19)	0.0089 (18)
C21	0.049 (2)	0.090 (3)	0.095 (3)	−0.0093 (19)	0.020 (2)	0.023 (2)
C22	0.0494 (18)	0.0416 (15)	0.065 (2)	−0.0016 (13)	0.0079 (15)	−0.0036 (15)
C23	0.070 (3)	0.073 (3)	0.126 (4)	0.011 (2)	0.042 (3)	−0.005 (2)
C24	0.119 (4)	0.080 (3)	0.129 (5)	0.011 (3)	−0.007 (3)	−0.056 (3)

Ni1—O1	1.993 (2)	C8—H8A	0.9700
Ni1—O2	2.0069 (19)	C8—H8B	0.9700
Ni1—N1	2.046 (2)	C9—C10	1.520 (5)
Ni1—N2	2.046 (2)	C9—H9A	0.9700
Ni1—O3	2.1370 (19)	C9—H9B	0.9700
Ni1—O4	2.1684 (19)	C10—C11	1.520 (4)
Cl1—C2	1.742 (3)	C10—H10A	0.9700
Cl2—C4	1.753 (3)	C10—H10B	0.9700
Cl3—C17	1.738 (3)	C11—H11A	0.9700
Cl4—C15	1.748 (3)	C11—H11B	0.9700
O1—C1	1.288 (3)	C12—C13	1.444 (4)
O2—C18	1.279 (3)	C12—H12	0.9300
O3—C19	1.229 (3)	C13—C14	1.408 (4)
O4—C22	1.232 (4)	C13—C18	1.425 (4)
N1—C7	1.279 (4)	C14—C15	1.364 (4)
N1—C8	1.473 (3)	C14—H14	0.9300
N2—C12	1.280 (4)	C15—C16	1.381 (5)
N2—C11	1.470 (3)	C16—C17	1.370 (4)
N3—C19	1.328 (4)	C16—H16	0.9300
N3—C20	1.451 (4)	C17—C18	1.436 (4)
N3—C21	1.452 (4)	C19—H19	0.9300
N4—C22	1.315 (4)	C20—H20A	0.9600
N4—C23	1.445 (5)	C20—H20B	0.9600
N4—C24	1.462 (5)	C20—H20C	0.9600
C1—C2	1.421 (4)	C21—H21A	0.9600
C1—C6	1.423 (4)	C21—H21B	0.9600
C2—C3	1.368 (4)	C21—H21C	0.9600
C3—C4	1.389 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—H23A	0.9600
C4—C5	1.365 (4)	C23—H23B	0.9600
C5—C6	1.393 (4)	C23—H23C	0.9600
C5—H5	0.9300	C24—H24A	0.9600
C6—C7	1.450 (4)	C24—H24B	0.9600
C7—H7	0.9300	C24—H24C	0.9600
C8—C9	1.526 (4)
O1—Ni1—O2	89.39 (8)	C11—C10—C9	116.1 (3)
O1—Ni1—N1	90.68 (9)	C11—C10—H10A	108.3
O2—Ni1—N1	91.73 (9)	C9—C10—H10A	108.3
O1—Ni1—N2	174.92 (8)	C11—C10—H10B	108.3
O2—Ni1—N2	90.14 (9)	C9—C10—H10B	108.3
N1—Ni1—N2	94.39 (9)	H10A—C10—H10B	107.4
O1—Ni1—O3	87.48 (8)	N2—C11—C10	111.5 (2)
O2—Ni1—O3	89.95 (8)	N2—C11—H11A	109.3
N1—Ni1—O3	177.50 (9)	C10—C11—H11A	109.3
N2—Ni1—O3	87.46 (9)	N2—C11—H11B	109.3
O1—Ni1—O4	86.86 (8)	C10—C11—H11B	109.3
O2—Ni1—O4	175.86 (8)	H11A—C11—H11B	108.0
N1—Ni1—O4	90.08 (8)	N2—C12—C13	127.9 (3)
N2—Ni1—O4	93.44 (9)	N2—C12—H12	116.1
O3—Ni1—O4	88.13 (8)	C13—C12—H12	116.1
C1—O1—Ni1	126.97 (17)	C14—C13—C18	120.9 (3)
C18—O2—Ni1	128.06 (19)	C14—C13—C12	116.2 (3)
C19—O3—Ni1	118.2 (2)	C18—C13—C12	122.8 (3)
C22—O4—Ni1	120.2 (2)	C15—C14—C13	120.8 (3)
C7—N1—C8	116.6 (2)	C15—C14—H14	119.6
C7—N1—Ni1	122.67 (18)	C13—C14—H14	119.6
C8—N1—Ni1	120.01 (19)	C14—C15—C16	120.8 (3)
C12—N2—C11	116.3 (3)	C14—C15—Cl4	120.5 (3)
C12—N2—Ni1	124.1 (2)	C16—C15—Cl4	118.6 (2)
C11—N2—Ni1	119.52 (19)	C17—C16—C15	119.2 (3)
C19—N3—C20	121.1 (3)	C17—C16—H16	120.4
C19—N3—C21	121.1 (3)	C15—C16—H16	120.4
C20—N3—C21	117.7 (3)	C16—C17—C18	123.7 (3)
C22—N4—C23	121.5 (3)	C16—C17—Cl3	118.8 (2)
C22—N4—C24	121.1 (3)	C18—C17—Cl3	117.5 (2)
C23—N4—C24	117.4 (3)	O2—C18—C13	125.1 (3)
O1—C1—C2	120.3 (2)	O2—C18—C17	120.3 (3)
O1—C1—C6	124.4 (3)	C13—C18—C17	114.6 (3)
C2—C1—C6	115.3 (3)	O3—C19—N3	124.4 (3)
C3—C2—C1	124.2 (3)	O3—C19—H19	117.8
C3—C2—Cl1	119.2 (2)	N3—C19—H19	117.8
C1—C2—Cl1	116.6 (2)	N3—C20—H20A	109.5
C2—C3—C4	118.1 (3)	N3—C20—H20B	109.5
C2—C3—H3	121.0	H20A—C20—H20B	109.5
C4—C3—H3	121.0	N3—C20—H20C	109.5
C5—C4—C3	120.7 (3)	H20A—C20—H20C	109.5
C5—C4—Cl2	119.6 (2)	H20B—C20—H20C	109.5
C3—C4—Cl2	119.7 (3)	N3—C21—H21A	109.5
C4—C5—C6	121.5 (3)	N3—C21—H21B	109.5
C4—C5—H5	119.3	H21A—C21—H21B	109.5
C6—C5—H5	119.3	N3—C21—H21C	109.5
C5—C6—C1	120.2 (3)	H21A—C21—H21C	109.5
C5—C6—C7	116.9 (2)	H21B—C21—H21C	109.5
C1—C6—C7	122.9 (3)	O4—C22—N4	124.4 (3)
N1—C7—C6	128.2 (2)	O4—C22—H22	117.8
N1—C7—H7	115.9	N4—C22—H22	117.8
C6—C7—H7	115.9	N4—C23—H23A	109.5
N1—C8—C9	113.9 (2)	N4—C23—H23B	109.5
N1—C8—H8A	108.8	H23A—C23—H23B	109.5
C9—C8—H8A	108.8	N4—C23—H23C	109.5
N1—C8—H8B	108.8	H23A—C23—H23C	109.5
C9—C8—H8B	108.8	H23B—C23—H23C	109.5
H8A—C8—H8B	107.7	N4—C24—H24A	109.5
C10—C9—C8	115.3 (3)	N4—C24—H24B	109.5
C10—C9—H9A	108.4	H24A—C24—H24B	109.5
C8—C9—H9A	108.4	N4—C24—H24C	109.5
C10—C9—H9B	108.4	H24A—C24—H24C	109.5
C8—C9—H9B	108.4	H24B—C24—H24C	109.5
H9A—C9—H9B	107.5
O2—Ni1—O1—C1	−69.9 (2)	C4—C5—C6—C7	−178.8 (2)
N1—Ni1—O1—C1	21.8 (2)	O1—C1—C6—C5	−179.0 (2)
O3—Ni1—O1—C1	−159.9 (2)	C2—C1—C6—C5	−0.8 (4)
O4—Ni1—O1—C1	111.9 (2)	O1—C1—C6—C7	−0.6 (4)
O1—Ni1—O2—C18	−161.0 (2)	C2—C1—C6—C7	177.6 (2)
N1—Ni1—O2—C18	108.4 (2)	C8—N1—C7—C6	179.8 (3)
N2—Ni1—O2—C18	14.0 (2)	Ni1—N1—C7—C6	9.7 (4)
O3—Ni1—O2—C18	−73.5 (2)	C5—C6—C7—N1	−177.9 (3)
O1—Ni1—O3—C19	27.0 (2)	C1—C6—C7—N1	3.7 (4)
O2—Ni1—O3—C19	−62.4 (2)	C7—N1—C8—C9	129.0 (3)
N2—Ni1—O3—C19	−152.6 (2)	Ni1—N1—C8—C9	−60.6 (3)
O4—Ni1—O3—C19	113.9 (2)	N1—C8—C9—C10	101.6 (3)
O1—Ni1—O4—C22	15.5 (2)	C8—C9—C10—C11	−74.4 (3)
N1—Ni1—O4—C22	106.2 (2)	C12—N2—C11—C10	93.9 (3)
N2—Ni1—O4—C22	−159.4 (2)	Ni1—N2—C11—C10	−88.3 (3)
O3—Ni1—O4—C22	−72.0 (2)	C9—C10—C11—N2	60.4 (4)
O1—Ni1—N1—C7	−18.0 (2)	C11—N2—C12—C13	−173.9 (3)
O2—Ni1—N1—C7	71.5 (2)	Ni1—N2—C12—C13	8.4 (4)
N2—Ni1—N1—C7	161.7 (2)	N2—C12—C13—C14	178.4 (3)
O4—Ni1—N1—C7	−104.8 (2)	N2—C12—C13—C18	2.3 (4)
O1—Ni1—N1—C8	172.2 (2)	C18—C13—C14—C15	−0.8 (4)
O2—Ni1—N1—C8	−98.3 (2)	C12—C13—C14—C15	−177.0 (3)
N2—Ni1—N1—C8	−8.1 (2)	C13—C14—C15—C16	0.6 (5)
O4—Ni1—N1—C8	85.4 (2)	C13—C14—C15—Cl4	179.3 (2)
N1—Ni1—N2—C12	−105.1 (2)	C14—C15—C16—C17	−0.4 (5)
O3—Ni1—N2—C12	76.6 (2)	Cl4—C15—C16—C17	−179.1 (2)
O4—Ni1—N2—C12	164.6 (2)	C15—C16—C17—C18	0.3 (4)
O2—Ni1—N2—C11	169.0 (2)	C15—C16—C17—Cl3	179.3 (2)
N1—Ni1—N2—C11	77.3 (2)	Ni1—O2—C18—C13	−8.8 (4)
O3—Ni1—N2—C11	−101.0 (2)	Ni1—O2—C18—C17	172.30 (18)
O4—Ni1—N2—C11	−13.1 (2)	C14—C13—C18—O2	−178.4 (3)
Ni1—O1—C1—C2	165.65 (18)	C12—C13—C18—O2	−2.4 (4)
Ni1—O1—C1—C6	−16.2 (4)	C14—C13—C18—C17	0.6 (4)
O1—C1—C2—C3	179.0 (3)	C12—C13—C18—C17	176.6 (2)
C6—C1—C2—C3	0.6 (4)	C16—C17—C18—O2	178.6 (3)
O1—C1—C2—Cl1	−1.0 (3)	Cl3—C17—C18—O2	−0.4 (3)
C6—C1—C2—Cl1	−179.33 (19)	C16—C17—C18—C13	−0.4 (4)
C1—C2—C3—C4	0.6 (4)	Cl3—C17—C18—C13	−179.41 (19)
Cl1—C2—C3—C4	−179.4 (2)	Ni1—O3—C19—N3	169.0 (2)
C2—C3—C4—C5	−1.7 (4)	C20—N3—C19—O3	−1.0 (5)
C2—C3—C4—Cl2	178.5 (2)	C21—N3—C19—O3	174.7 (3)
C3—C4—C5—C6	1.6 (4)	Ni1—O4—C22—N4	−161.8 (3)
Cl2—C4—C5—C6	−178.6 (2)	C23—N4—C22—O4	−2.2 (5)
C4—C5—C6—C1	−0.3 (4)	C24—N4—C22—O4	−178.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O4	0.97	2.58	3.327 (4)	134
C11—H11B···O4	0.97	2.40	3.057 (4)	125
C19—H19···O1	0.93	2.25	2.865 (4)	123
C8—H8A···Cl3i	0.97	2.86	3.753 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O4	0.97	2.58	3.327 (4)	134
C11—H11B⋯O4	0.97	2.40	3.057 (4)	125
C19—H19⋯O1	0.93	2.25	2.865 (4)	123
C8—H8A⋯Cl3i	0.97	2.86	3.753 (3)	153

Symmetry code: (i) .