Dichloridobis(phenyl 2-pyridyl ketone oxime)nickel(II) acetone solvate.

The Ni atom in the title compound, [NiCl(2)(C(12)H(10)N(2)O)(2)]·C(3)H(6)O, adopts a distorted octa-hedral geometry, being ligated by four N atoms from two different phenyl 2-pyridyl ketone oxime ligands and two Cl atoms. In the crystal structure, inter-molecular O-H⋯Cl hydrogen bonds link the mol-ecules into a chain structure along [010]. There is a π-π contact between the pyridine rings [centroid-centroid distance = 3.824 (5) Å].

Related literature

For related structures, see: Korpi et al. (2005 ▶); Pearse et al. (1989 ▶); Afrati et al. (2005 ▶); Stamatatos et al. (2006 ▶); Papatriantafyllopoulou et al. (2007 ▶).

Experimental

Crystal data

[NiCl2(C12H10N2O)2]·C3H6O

M = 584.13

Triclinic,

a = 9.0367 (11) Å

b = 12.9142 (16) Å

c = 13.0664 (16) Å

α = 105.4390 (10)°

β = 92.232 (2)°

γ = 108.183 (2)°

V = 1384.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.93 mm−1

T = 296 (2) K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.822, T max = 0.866

6839 measured reflections

4761 independent reflections

4002 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.05

4761 reflections

338 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043961/at2700sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043961/at2700Isup2.hkl

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

[NiCl2(C12H10N2O)2]·C3H6O	Z = 2
Mr = 584.13	F(000) = 604
Triclinic, P1	Dx = 1.402 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0367 (11) Å	Cell parameters from 3432 reflections
b = 12.9142 (16) Å	θ = 2.4–27.6°
c = 13.0664 (16) Å	µ = 0.93 mm−1
α = 105.439 (1)°	T = 296 K
β = 92.232 (2)°	Block, dark cyan
γ = 108.183 (2)°	0.22 × 0.18 × 0.16 mm
V = 1384.0 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	4761 independent reflections
Radiation source: sealed tube	4002 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→6
Tmin = 0.822, Tmax = 0.866	k = −10→15
6839 measured reflections	l = −15→15

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3
4761 reflections	(Δ/σ)max < 0.001
338 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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. H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms. The highest peak is located 1.10 Å from atom Cl1.

	x	y	z	Uiso*/Ueq
Ni1	0.34978 (3)	0.11803 (2)	0.295182 (19)	0.03252 (11)
Cl1	0.43421 (6)	0.11649 (4)	0.47059 (4)	0.03838 (15)
Cl2	0.61388 (7)	0.19661 (5)	0.25662 (5)	0.04710 (16)
O1	0.3728 (2)	−0.11019 (13)	0.29824 (12)	0.0508 (4)
H1	0.4028	−0.0694	0.3602	0.076*
O2	0.45576 (19)	0.36884 (13)	0.31744 (15)	0.0519 (4)
H2	0.5345	0.3509	0.3069	0.078*
O3	0.8381 (3)	0.7143 (2)	0.2311 (2)	0.0984 (8)
N1	0.3351 (2)	−0.04856 (15)	0.23669 (13)	0.0373 (4)
N2	0.2672 (2)	0.07731 (16)	0.13055 (14)	0.0380 (4)
N3	0.3367 (2)	0.27794 (14)	0.33148 (14)	0.0367 (4)
N4	0.1224 (2)	0.09447 (14)	0.33492 (13)	0.0327 (4)
C1	0.2320 (3)	0.1443 (2)	0.07928 (19)	0.0488 (6)
H1A	0.2365	0.2169	0.1190	0.059*
C2	0.1888 (3)	0.1112 (2)	−0.0308 (2)	0.0579 (7)
H2A	0.1652	0.1604	−0.0643	0.070*
C3	0.1820 (3)	0.0046 (3)	−0.0884 (2)	0.0629 (8)
H3	0.1555	−0.0193	−0.1624	0.076*
C4	0.2143 (3)	−0.0681 (2)	−0.03703 (18)	0.0527 (6)
H4	0.2073	−0.1416	−0.0756	0.063*
C5	0.2575 (3)	−0.02919 (19)	0.07348 (17)	0.0395 (5)
C6	0.2956 (2)	−0.10087 (18)	0.13567 (16)	0.0368 (5)
C7	0.2878 (3)	−0.21931 (19)	0.08362 (17)	0.0416 (5)
C8	0.1900 (3)	−0.3086 (2)	0.1158 (2)	0.0586 (7)
H8	0.1293	−0.2939	0.1701	0.070*
C9	0.1835 (4)	−0.4189 (2)	0.0668 (2)	0.0736 (9)
H9	0.1187	−0.4784	0.0887	0.088*
C10	0.2724 (4)	−0.4419 (2)	−0.0146 (2)	0.0737 (9)
H10	0.2667	−0.5166	−0.0476	0.088*
C11	0.3686 (4)	−0.3545 (2)	−0.0462 (2)	0.0672 (8)
H11	0.4291	−0.3699	−0.1006	0.081*
C12	0.3768 (3)	−0.2433 (2)	0.00211 (18)	0.0501 (6)
H12	0.4424	−0.1843	−0.0202	0.060*
C13	0.0213 (3)	0.00010 (18)	0.34823 (17)	0.0396 (5)
H13	0.0474	−0.0661	0.3316	0.047*
C14	−0.1203 (3)	−0.0034 (2)	0.38561 (19)	0.0464 (6)
H14	−0.1876	−0.0707	0.3942	0.056*
C15	−0.1606 (3)	0.0934 (2)	0.40997 (18)	0.0463 (6)
H15	−0.2558	0.0926	0.4349	0.056*
C16	−0.0576 (3)	0.1920 (2)	0.39698 (17)	0.0413 (5)
H16	−0.0826	0.2587	0.4129	0.050*
C17	0.0833 (2)	0.19055 (17)	0.36005 (15)	0.0322 (5)
C18	0.2045 (2)	0.29384 (17)	0.34868 (16)	0.0348 (5)
C19	0.1721 (3)	0.40061 (18)	0.35581 (17)	0.0387 (5)
C20	0.0436 (3)	0.3987 (2)	0.2929 (2)	0.0516 (6)
H20	−0.0242	0.3298	0.2481	0.062*
C21	0.0160 (4)	0.4993 (2)	0.2966 (2)	0.0644 (8)
H21	−0.0702	0.4977	0.2541	0.077*
C22	0.1154 (4)	0.6011 (2)	0.3627 (2)	0.0652 (8)
H22	0.0971	0.6684	0.3641	0.078*
C23	0.2412 (4)	0.6044 (2)	0.4266 (2)	0.0614 (7)
H23	0.3073	0.6736	0.4719	0.074*
C24	0.2703 (3)	0.50456 (19)	0.42393 (19)	0.0496 (6)
H24	0.3557	0.5070	0.4678	0.060*
C25	0.5679 (5)	0.6853 (5)	0.2243 (3)	0.145 (2)
H25A	0.5795	0.7050	0.1586	0.217*
H25B	0.5336	0.7397	0.2742	0.217*
H25C	0.4915	0.6106	0.2105	0.217*
C26	0.7191 (4)	0.6861 (2)	0.2698 (2)	0.0583 (7)
C27	0.7140 (4)	0.6509 (3)	0.3687 (3)	0.0836 (10)
H27A	0.8184	0.6597	0.3968	0.125*
H27B	0.6489	0.5724	0.3527	0.125*
H27C	0.6714	0.6975	0.4208	0.125*

	U11	U22	U33	U12	U13	U23
Ni1	0.03109 (17)	0.04030 (18)	0.02937 (16)	0.01737 (13)	0.00755 (12)	0.00847 (12)
Cl1	0.0403 (3)	0.0461 (3)	0.0298 (3)	0.0176 (2)	0.0057 (2)	0.0091 (2)
Cl2	0.0343 (3)	0.0692 (4)	0.0458 (3)	0.0239 (3)	0.0149 (3)	0.0207 (3)
O1	0.0746 (13)	0.0499 (10)	0.0325 (8)	0.0323 (9)	−0.0012 (8)	0.0069 (7)
O2	0.0356 (10)	0.0444 (9)	0.0774 (12)	0.0109 (8)	0.0200 (9)	0.0219 (8)
O3	0.0952 (19)	0.0966 (17)	0.1112 (19)	0.0373 (14)	0.0510 (16)	0.0313 (14)
N1	0.0432 (11)	0.0461 (10)	0.0289 (10)	0.0238 (9)	0.0058 (8)	0.0106 (8)
N2	0.0323 (10)	0.0534 (11)	0.0329 (10)	0.0193 (9)	0.0071 (8)	0.0139 (8)
N3	0.0315 (10)	0.0380 (10)	0.0407 (10)	0.0110 (8)	0.0092 (8)	0.0119 (8)
N4	0.0311 (10)	0.0380 (10)	0.0303 (9)	0.0151 (8)	0.0043 (7)	0.0081 (7)
C1	0.0470 (15)	0.0607 (15)	0.0455 (14)	0.0250 (12)	0.0089 (11)	0.0179 (12)
C2	0.0610 (18)	0.0815 (19)	0.0443 (15)	0.0328 (15)	0.0056 (13)	0.0294 (14)
C3	0.0678 (19)	0.093 (2)	0.0307 (13)	0.0324 (16)	0.0005 (12)	0.0163 (14)
C4	0.0563 (17)	0.0718 (17)	0.0315 (12)	0.0300 (14)	0.0017 (11)	0.0081 (12)
C5	0.0318 (12)	0.0545 (14)	0.0316 (12)	0.0171 (11)	0.0052 (9)	0.0085 (10)
C6	0.0321 (12)	0.0482 (13)	0.0306 (11)	0.0163 (10)	0.0076 (9)	0.0081 (10)
C7	0.0412 (14)	0.0467 (13)	0.0305 (12)	0.0147 (11)	−0.0003 (10)	0.0016 (10)
C8	0.0563 (17)	0.0578 (17)	0.0501 (15)	0.0099 (13)	0.0131 (13)	0.0068 (12)
C9	0.084 (2)	0.0482 (17)	0.069 (2)	0.0041 (15)	0.0085 (17)	0.0073 (14)
C10	0.109 (3)	0.0476 (16)	0.0538 (17)	0.0278 (17)	0.0028 (17)	−0.0041 (13)
C11	0.094 (2)	0.0696 (19)	0.0435 (15)	0.0437 (18)	0.0186 (15)	0.0057 (13)
C12	0.0602 (17)	0.0531 (15)	0.0385 (13)	0.0252 (13)	0.0129 (12)	0.0076 (11)
C13	0.0404 (13)	0.0410 (12)	0.0396 (12)	0.0156 (11)	0.0067 (10)	0.0130 (10)
C14	0.0387 (14)	0.0510 (14)	0.0494 (14)	0.0098 (11)	0.0110 (11)	0.0198 (11)
C15	0.0319 (13)	0.0618 (15)	0.0475 (14)	0.0174 (11)	0.0137 (11)	0.0165 (12)
C16	0.0348 (13)	0.0499 (14)	0.0420 (13)	0.0215 (11)	0.0093 (10)	0.0088 (10)
C17	0.0311 (12)	0.0379 (11)	0.0268 (10)	0.0131 (9)	0.0026 (9)	0.0064 (8)
C18	0.0328 (12)	0.0382 (11)	0.0319 (11)	0.0141 (10)	0.0039 (9)	0.0053 (9)
C19	0.0379 (13)	0.0387 (12)	0.0421 (12)	0.0174 (10)	0.0123 (10)	0.0098 (10)
C20	0.0562 (16)	0.0506 (14)	0.0491 (14)	0.0266 (13)	−0.0020 (12)	0.0073 (11)
C21	0.077 (2)	0.0723 (19)	0.0619 (18)	0.0486 (17)	0.0068 (15)	0.0216 (15)
C22	0.086 (2)	0.0531 (17)	0.0743 (19)	0.0423 (16)	0.0262 (17)	0.0230 (15)
C23	0.0629 (19)	0.0396 (14)	0.0752 (19)	0.0170 (13)	0.0205 (15)	0.0050 (13)
C24	0.0458 (15)	0.0444 (14)	0.0553 (15)	0.0162 (11)	0.0096 (12)	0.0077 (11)
C25	0.119 (4)	0.261 (6)	0.089 (3)	0.113 (4)	0.001 (3)	0.051 (3)
C26	0.0649 (19)	0.0529 (16)	0.0536 (16)	0.0272 (14)	0.0089 (15)	0.0010 (12)
C27	0.090 (3)	0.101 (2)	0.073 (2)	0.049 (2)	0.0144 (18)	0.0263 (18)

Ni1—N3	2.0344 (18)	C10—H10	0.9300
Ni1—N1	2.0418 (18)	C11—C12	1.384 (3)
Ni1—N4	2.0879 (17)	C11—H11	0.9300
Ni1—N2	2.1188 (17)	C12—H12	0.9300
Ni1—Cl1	2.3944 (6)	C13—C14	1.379 (3)
Ni1—Cl2	2.4153 (7)	C13—H13	0.9300
O1—N1	1.373 (2)	C14—C15	1.370 (3)
O1—H1	0.8200	C14—H14	0.9300
O2—N3	1.383 (2)	C15—C16	1.381 (3)
O2—H2	0.8200	C15—H15	0.9300
O3—C26	1.200 (3)	C16—C17	1.382 (3)
N1—C6	1.290 (3)	C16—H16	0.9300
N2—C1	1.328 (3)	C17—C18	1.486 (3)
N2—C5	1.352 (3)	C18—C19	1.477 (3)
N3—C18	1.292 (3)	C19—C20	1.386 (3)
N4—C13	1.335 (3)	C19—C24	1.393 (3)
N4—C17	1.356 (3)	C20—C21	1.386 (3)
C1—C2	1.389 (3)	C20—H20	0.9300
C1—H1A	0.9300	C21—C22	1.371 (4)
C2—C3	1.363 (4)	C21—H21	0.9300
C2—H2A	0.9300	C22—C23	1.367 (4)
C3—C4	1.381 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.386 (3)
C4—C5	1.392 (3)	C23—H23	0.9300
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.488 (3)	C25—C26	1.464 (5)
C6—C7	1.477 (3)	C25—H25A	0.9600
C7—C12	1.387 (3)	C25—H25B	0.9600
C7—C8	1.392 (3)	C25—H25C	0.9600
C8—C9	1.380 (4)	C26—C27	1.477 (4)
C8—H8	0.9300	C27—H27A	0.9600
C9—C10	1.382 (4)	C27—H27B	0.9600
C9—H9	0.9300	C27—H27C	0.9600
C10—C11	1.365 (4)
N3—Ni1—N1	170.18 (7)	C9—C10—H10	120.1
N3—Ni1—N4	76.84 (7)	C10—C11—C12	120.4 (3)
N1—Ni1—N4	99.25 (7)	C10—C11—H11	119.8
N3—Ni1—N2	94.03 (7)	C12—C11—H11	119.8
N1—Ni1—N2	76.92 (7)	C11—C12—C7	120.3 (2)
N4—Ni1—N2	91.16 (7)	C11—C12—H12	119.9
N3—Ni1—Cl1	99.43 (5)	C7—C12—H12	119.9
N1—Ni1—Cl1	89.47 (5)	N4—C13—C14	122.8 (2)
N4—Ni1—Cl1	89.49 (5)	N4—C13—H13	118.6
N2—Ni1—Cl1	166.31 (5)	C14—C13—H13	118.6
N3—Ni1—Cl2	87.94 (5)	C15—C14—C13	119.2 (2)
N1—Ni1—Cl2	95.62 (6)	C15—C14—H14	120.4
N4—Ni1—Cl2	164.76 (5)	C13—C14—H14	120.4
N2—Ni1—Cl2	88.97 (5)	C14—C15—C16	119.0 (2)
Cl1—Ni1—Cl2	93.97 (2)	C14—C15—H15	120.5
N1—O1—H1	109.5	C16—C15—H15	120.5
N3—O2—H2	109.5	C15—C16—C17	119.2 (2)
C6—N1—O1	115.73 (17)	C15—C16—H16	120.4
C6—N1—Ni1	120.35 (15)	C17—C16—H16	120.4
O1—N1—Ni1	123.85 (12)	N4—C17—C16	121.86 (19)
C1—N2—C5	118.66 (19)	N4—C17—C18	115.20 (18)
C1—N2—Ni1	127.91 (16)	C16—C17—C18	122.9 (2)
C5—N2—Ni1	113.37 (14)	N3—C18—C19	125.41 (19)
C18—N3—O2	116.43 (18)	N3—C18—C17	112.33 (19)
C18—N3—Ni1	120.22 (14)	C19—C18—C17	122.25 (18)
O2—N3—Ni1	122.03 (13)	C20—C19—C24	118.9 (2)
C13—N4—C17	117.97 (18)	C20—C19—C18	120.0 (2)
C13—N4—Ni1	127.23 (15)	C24—C19—C18	121.1 (2)
C17—N4—Ni1	114.43 (13)	C19—C20—C21	120.2 (2)
N2—C1—C2	123.1 (2)	C19—C20—H20	119.9
N2—C1—H1A	118.4	C21—C20—H20	119.9
C2—C1—H1A	118.4	C22—C21—C20	120.2 (3)
C3—C2—C1	118.1 (2)	C22—C21—H21	119.9
C3—C2—H2A	121.0	C20—C21—H21	119.9
C1—C2—H2A	121.0	C23—C22—C21	120.4 (3)
C2—C3—C4	120.1 (2)	C23—C22—H22	119.8
C2—C3—H3	119.9	C21—C22—H22	119.8
C4—C3—H3	119.9	C22—C23—C24	120.1 (3)
C3—C4—C5	118.7 (2)	C22—C23—H23	119.9
C3—C4—H4	120.6	C24—C23—H23	119.9
C5—C4—H4	120.6	C23—C24—C19	120.2 (2)
N2—C5—C4	121.2 (2)	C23—C24—H24	119.9
N2—C5—C6	116.14 (18)	C19—C24—H24	119.9
C4—C5—C6	122.6 (2)	C26—C25—H25A	109.5
N1—C6—C7	125.2 (2)	C26—C25—H25B	109.5
N1—C6—C5	113.03 (19)	H25A—C25—H25B	109.5
C7—C6—C5	121.78 (18)	C26—C25—H25C	109.5
C12—C7—C8	119.1 (2)	H25A—C25—H25C	109.5
C12—C7—C6	120.7 (2)	H25B—C25—H25C	109.5
C8—C7—C6	120.2 (2)	O3—C26—C25	123.1 (3)
C9—C8—C7	119.8 (3)	O3—C26—C27	122.5 (3)
C9—C8—H8	120.1	C25—C26—C27	114.4 (3)
C7—C8—H8	120.1	C26—C27—H27A	109.5
C8—C9—C10	120.7 (3)	C26—C27—H27B	109.5
C8—C9—H9	119.7	H27A—C27—H27B	109.5
C10—C9—H9	119.7	C26—C27—H27C	109.5
C11—C10—C9	119.7 (3)	H27A—C27—H27C	109.5
C11—C10—H10	120.1	H27B—C27—H27C	109.5
N3—Ni1—N1—C6	26.9 (5)	O1—N1—C6—C7	0.3 (3)
N4—Ni1—N1—C6	92.66 (17)	Ni1—N1—C6—C7	177.24 (16)
N2—Ni1—N1—C6	3.62 (17)	O1—N1—C6—C5	−179.56 (17)
Cl1—Ni1—N1—C6	−177.94 (17)	Ni1—N1—C6—C5	−2.7 (3)
Cl2—Ni1—N1—C6	−84.00 (17)	N2—C5—C6—N1	−0.9 (3)
N3—Ni1—N1—O1	−156.4 (4)	C4—C5—C6—N1	179.0 (2)
N4—Ni1—N1—O1	−90.70 (17)	N2—C5—C6—C7	179.2 (2)
N2—Ni1—N1—O1	−179.74 (18)	C4—C5—C6—C7	−0.9 (3)
Cl1—Ni1—N1—O1	−1.30 (16)	N1—C6—C7—C12	−121.8 (3)
Cl2—Ni1—N1—O1	92.64 (16)	C5—C6—C7—C12	58.1 (3)
N3—Ni1—N2—C1	3.12 (19)	N1—C6—C7—C8	58.4 (3)
N1—Ni1—N2—C1	179.2 (2)	C5—C6—C7—C8	−121.7 (2)
N4—Ni1—N2—C1	80.01 (19)	C12—C7—C8—C9	0.2 (4)
Cl1—Ni1—N2—C1	172.62 (17)	C6—C7—C8—C9	−179.9 (2)
Cl2—Ni1—N2—C1	−84.74 (18)	C7—C8—C9—C10	−0.4 (5)
N3—Ni1—N2—C5	−179.93 (15)	C8—C9—C10—C11	0.6 (5)
N1—Ni1—N2—C5	−3.81 (14)	C9—C10—C11—C12	−0.5 (5)
N4—Ni1—N2—C5	−103.04 (15)	C10—C11—C12—C7	0.3 (4)
Cl1—Ni1—N2—C5	−10.4 (3)	C8—C7—C12—C11	−0.2 (4)
Cl2—Ni1—N2—C5	92.21 (14)	C6—C7—C12—C11	−180.0 (2)
N1—Ni1—N3—C18	59.8 (5)	C17—N4—C13—C14	0.4 (3)
N4—Ni1—N3—C18	−7.67 (16)	Ni1—N4—C13—C14	172.90 (16)
N2—Ni1—N3—C18	82.58 (17)	N4—C13—C14—C15	0.3 (3)
Cl1—Ni1—N3—C18	−94.92 (16)	C13—C14—C15—C16	−0.4 (3)
Cl2—Ni1—N3—C18	171.40 (16)	C14—C15—C16—C17	−0.1 (3)
N1—Ni1—N3—O2	−106.6 (4)	C13—N4—C17—C16	−0.9 (3)
N4—Ni1—N3—O2	−174.12 (17)	Ni1—N4—C17—C16	−174.40 (16)
N2—Ni1—N3—O2	−83.87 (16)	C13—N4—C17—C18	177.00 (17)
Cl1—Ni1—N3—O2	98.64 (15)	Ni1—N4—C17—C18	3.5 (2)
Cl2—Ni1—N3—O2	4.95 (15)	C15—C16—C17—N4	0.8 (3)
N3—Ni1—N4—C13	−171.15 (18)	C15—C16—C17—C18	−176.94 (19)
N1—Ni1—N4—C13	18.03 (18)	O2—N3—C18—C19	−0.9 (3)
N2—Ni1—N4—C13	94.97 (17)	Ni1—N3—C18—C19	−168.04 (16)
Cl1—Ni1—N4—C13	−71.35 (16)	O2—N3—C18—C17	178.61 (16)
Cl2—Ni1—N4—C13	−174.69 (13)	Ni1—N3—C18—C17	11.4 (2)
N3—Ni1—N4—C17	1.61 (13)	N4—C17—C18—N3	−9.5 (3)
N1—Ni1—N4—C17	−169.20 (13)	C16—C17—C18—N3	168.4 (2)
N2—Ni1—N4—C17	−92.26 (14)	N4—C17—C18—C19	170.02 (18)
Cl1—Ni1—N4—C17	101.42 (13)	C16—C17—C18—C19	−12.1 (3)
Cl2—Ni1—N4—C17	−1.9 (3)	N3—C18—C19—C20	127.1 (3)
C5—N2—C1—C2	−1.4 (3)	C17—C18—C19—C20	−52.4 (3)
Ni1—N2—C1—C2	175.42 (19)	N3—C18—C19—C24	−51.9 (3)
N2—C1—C2—C3	0.2 (4)	C17—C18—C19—C24	128.6 (2)
C1—C2—C3—C4	1.3 (4)	C24—C19—C20—C21	1.3 (4)
C2—C3—C4—C5	−1.6 (4)	C18—C19—C20—C21	−177.7 (2)
C1—N2—C5—C4	1.1 (3)	C19—C20—C21—C22	−0.2 (4)
Ni1—N2—C5—C4	−176.19 (18)	C20—C21—C22—C23	−0.9 (4)
C1—N2—C5—C6	−178.99 (19)	C21—C22—C23—C24	0.8 (4)
Ni1—N2—C5—C6	3.7 (2)	C22—C23—C24—C19	0.3 (4)
C3—C4—C5—N2	0.4 (4)	C20—C19—C24—C23	−1.4 (4)
C3—C4—C5—C6	−179.5 (2)	C18—C19—C24—C23	177.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl2	0.82	2.27	2.9582 (18)	142
O1—H1···Cl1i	0.82	2.91	3.4612 (16)	127
O1—H1···Cl1	0.82	2.37	3.0542 (16)	141

Table 1

Selected geometric parameters (Å, °)

Ni1—N3	2.0344 (18)
Ni1—N1	2.0418 (18)
Ni1—N4	2.0879 (17)
Ni1—N2	2.1188 (17)
Ni1—Cl1	2.3944 (6)
Ni1—Cl2	2.4153 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯Cl2	0.82	2.27	2.9582 (18)	142
O1—H1⋯Cl1i	0.82	2.91	3.4612 (16)	127
O1—H1⋯Cl1	0.82	2.37	3.0542 (16)	141

Symmetry code: (i) .