{4,4',6,6'-Tetra-chloro-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanylyl-idene)]}nickel(II).

In the title compound, [Ni(C(19)H(16)Cl(4)N(2)O(2))], the Ni(II) ion is in a distorted square-planar environment coordinated by two N atoms and two O atoms of the tetra-dentate ligand. The dihedral angle between the benzene rings is 24.8 (2)°. In the crystal, mol-ecules are linked into chains along the b axis by weak C-H⋯O and C-H⋯Cl inter-actions. An inter-molecular Cl⋯Cl [3.4564 (19) Å] inter-action is present which is shorter than the sum of the van der Waals radii of Cl atoms (3.50 Å).

Related literature

For applications of Schiff bases in coordination chemistry, see: Granovski et al. (1993 ▶); Blower et al. (1998 ▶). For related structures see: Ghaemi et al. (2011 ▶); Kargar et al. (2011 ▶, 2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Ni(C19H16Cl4N2O2)]

M = 504.85

Monoclinic,

a = 12.4019 (8) Å

b = 8.1883 (6) Å

c = 20.3945 (13) Å

β = 96.680 (3)°

V = 2057.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.48 mm−1

T = 291 K

0.25 × 0.18 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.694, T max = 0.871

17449 measured reflections

4874 independent reflections

2682 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.127

S = 1.05

4874 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002085/lh5404sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002085/lh5404Isup2.hkl

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

[Ni(C19H16Cl4N2O2)]	F(000) = 1024
Mr = 504.85	Dx = 1.630 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2540 reflections
a = 12.4019 (8) Å	θ = 2.5–27.4°
b = 8.1883 (6) Å	µ = 1.48 mm−1
c = 20.3945 (13) Å	T = 291 K
β = 96.680 (3)°	Block, dark-red
V = 2057.0 (2) Å3	0.25 × 0.18 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4874 independent reflections
Radiation source: fine-focus sealed tube	2682 reflections with I > 2σ(I)
graphite	Rint = 0.090
φ and ω scans	θmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→15
Tmin = 0.694, Tmax = 0.871	k = −10→7
17449 measured reflections	l = −26→26

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0401P)2 + 1.6535P] where P = (Fo2 + 2Fc2)/3
4874 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.41 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
C1	0.4518 (3)	0.3786 (5)	−0.1322 (2)	0.0284 (10)
C2	0.3696 (3)	0.3864 (6)	−0.1865 (2)	0.0329 (11)
C3	0.3866 (4)	0.4565 (6)	−0.2451 (2)	0.0396 (12)
H3	0.3311	0.4580	−0.2799	0.047*
C4	0.4868 (4)	0.5257 (6)	−0.2527 (2)	0.0390 (12)
C5	0.5684 (4)	0.5219 (6)	−0.2020 (2)	0.0371 (12)
H5	0.6350	0.5693	−0.2073	0.044*
C6	0.5530 (3)	0.4470 (6)	−0.1417 (2)	0.0322 (11)
C7	0.6396 (3)	0.4527 (5)	−0.0889 (2)	0.0331 (11)
H7	0.7009	0.5123	−0.0961	0.040*
C8	0.7307 (3)	0.4234 (6)	0.0187 (2)	0.0371 (12)
H8A	0.7009	0.4640	0.0574	0.044*
H8B	0.7742	0.5098	0.0025	0.044*
C9	0.8032 (3)	0.2782 (5)	0.0382 (2)	0.0338 (11)
C10	0.8628 (5)	0.3121 (7)	0.1068 (3)	0.0632 (17)
H10A	0.8112	0.3181	0.1383	0.095*
H10B	0.9011	0.4138	0.1062	0.095*
H10C	0.9135	0.2256	0.1189	0.095*
C11	0.8856 (4)	0.2535 (7)	−0.0109 (3)	0.0626 (16)
H11A	0.9338	0.3455	−0.0091	0.094*
H11B	0.8481	0.2436	−0.0546	0.094*
H11C	0.9266	0.1559	0.0002	0.094*
C12	0.7341 (3)	0.1245 (6)	0.0386 (2)	0.0382 (12)
H12A	0.7265	0.0769	−0.0052	0.046*
H12B	0.7717	0.0459	0.0687	0.046*
C13	0.6000 (4)	0.0806 (6)	0.1105 (2)	0.0356 (11)
H13	0.6551	0.0239	0.1356	0.043*
C14	0.4951 (3)	0.0785 (6)	0.1330 (2)	0.0320 (11)
C15	0.4848 (4)	0.0125 (6)	0.1952 (2)	0.0442 (13)
H15	0.5461	−0.0254	0.2213	0.053*
C16	0.3867 (4)	0.0033 (6)	0.2179 (2)	0.0447 (13)
C17	0.2938 (4)	0.0556 (6)	0.1791 (2)	0.0409 (12)
H17	0.2265	0.0493	0.1949	0.049*
C18	0.3019 (3)	0.1168 (6)	0.1174 (2)	0.0325 (11)
C19	0.4025 (3)	0.1323 (5)	0.0910 (2)	0.0310 (11)
Cl1	0.24344 (10)	0.30295 (16)	−0.17810 (7)	0.0511 (4)
Cl2	0.50613 (11)	0.6188 (2)	−0.32739 (6)	0.0619 (4)
Cl3	0.37569 (12)	−0.0781 (2)	0.29595 (7)	0.0770 (5)
Cl4	0.18413 (9)	0.18304 (15)	0.07001 (6)	0.0390 (3)
N1	0.6402 (3)	0.3834 (5)	−0.03285 (17)	0.0314 (9)
N2	0.6250 (3)	0.1539 (5)	0.05842 (18)	0.0330 (9)
Ni1	0.52748 (4)	0.26003 (7)	−0.00440 (3)	0.02984 (17)
O1	0.4305 (2)	0.3113 (4)	−0.07708 (14)	0.0357 (8)
O2	0.4051 (2)	0.1881 (4)	0.03171 (14)	0.0342 (7)

	U11	U22	U33	U12	U13	U23
C1	0.022 (2)	0.025 (3)	0.039 (2)	0.0036 (19)	0.0069 (19)	−0.005 (2)
C2	0.031 (2)	0.027 (3)	0.041 (3)	0.001 (2)	0.002 (2)	−0.003 (2)
C3	0.035 (3)	0.038 (3)	0.043 (3)	0.004 (2)	−0.002 (2)	−0.006 (2)
C4	0.043 (3)	0.036 (3)	0.039 (3)	0.010 (2)	0.006 (2)	0.000 (2)
C5	0.027 (2)	0.045 (3)	0.041 (3)	−0.003 (2)	0.011 (2)	0.000 (2)
C6	0.030 (2)	0.029 (3)	0.039 (3)	0.001 (2)	0.0066 (19)	−0.002 (2)
C7	0.028 (2)	0.027 (3)	0.044 (3)	−0.005 (2)	0.005 (2)	−0.004 (2)
C8	0.031 (2)	0.036 (3)	0.044 (3)	−0.008 (2)	−0.001 (2)	−0.005 (2)
C9	0.028 (2)	0.027 (3)	0.046 (3)	0.000 (2)	0.003 (2)	−0.006 (2)
C10	0.061 (4)	0.053 (4)	0.069 (4)	0.001 (3)	−0.024 (3)	−0.003 (3)
C11	0.041 (3)	0.061 (4)	0.091 (4)	−0.005 (3)	0.025 (3)	−0.001 (3)
C12	0.031 (3)	0.031 (3)	0.054 (3)	0.005 (2)	0.009 (2)	−0.008 (2)
C13	0.030 (2)	0.030 (3)	0.046 (3)	0.001 (2)	−0.001 (2)	0.003 (2)
C14	0.027 (2)	0.028 (3)	0.041 (3)	0.001 (2)	0.004 (2)	−0.001 (2)
C15	0.035 (3)	0.043 (4)	0.053 (3)	−0.001 (2)	0.001 (2)	0.014 (3)
C16	0.041 (3)	0.052 (4)	0.042 (3)	0.000 (2)	0.007 (2)	0.013 (2)
C17	0.034 (3)	0.040 (3)	0.051 (3)	−0.008 (2)	0.015 (2)	0.003 (2)
C18	0.032 (2)	0.026 (3)	0.040 (3)	0.001 (2)	0.006 (2)	−0.001 (2)
C19	0.028 (2)	0.021 (3)	0.044 (3)	−0.0025 (19)	0.005 (2)	−0.005 (2)
Cl1	0.0323 (6)	0.0514 (9)	0.0667 (8)	−0.0087 (6)	−0.0056 (6)	0.0055 (7)
Cl2	0.0578 (9)	0.0838 (12)	0.0461 (8)	0.0107 (8)	0.0139 (6)	0.0175 (7)
Cl3	0.0539 (9)	0.1181 (15)	0.0603 (9)	0.0003 (9)	0.0124 (7)	0.0444 (9)
Cl4	0.0269 (6)	0.0416 (8)	0.0489 (7)	0.0010 (5)	0.0061 (5)	0.0017 (6)
N1	0.0261 (19)	0.029 (2)	0.039 (2)	−0.0021 (16)	0.0024 (16)	−0.0054 (18)
N2	0.0257 (19)	0.028 (2)	0.046 (2)	0.0007 (17)	0.0076 (17)	−0.0085 (19)
Ni1	0.0238 (3)	0.0288 (4)	0.0374 (3)	−0.0009 (3)	0.0056 (2)	−0.0023 (3)
O1	0.0227 (15)	0.041 (2)	0.0445 (18)	−0.0029 (14)	0.0090 (13)	0.0015 (15)
O2	0.0277 (16)	0.040 (2)	0.0354 (17)	−0.0030 (14)	0.0052 (13)	0.0016 (14)

C1—O1	1.306 (5)	C11—H11A	0.9600
C1—C6	1.408 (6)	C11—H11B	0.9600
C1—C2	1.417 (5)	C11—H11C	0.9600
C2—C3	1.363 (6)	C12—N2	1.477 (5)
C2—Cl1	1.734 (5)	C12—H12A	0.9700
C3—C4	1.392 (6)	C12—H12B	0.9700
C3—H3	0.9300	C13—N2	1.289 (5)
C4—C5	1.360 (6)	C13—C14	1.429 (6)
C4—Cl2	1.744 (5)	C13—H13	0.9300
C5—C6	1.408 (6)	C14—C15	1.397 (6)
C5—H5	0.9300	C14—C19	1.421 (6)
C6—C7	1.430 (6)	C15—C16	1.354 (7)
C7—N1	1.276 (5)	C15—H15	0.9300
C7—H7	0.9300	C16—C17	1.387 (6)
C8—N1	1.482 (5)	C16—Cl3	1.746 (5)
C8—C9	1.516 (6)	C17—C18	1.369 (6)
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700	C18—C19	1.421 (6)
C9—C12	1.523 (6)	C18—Cl4	1.742 (4)
C9—C11	1.524 (7)	C19—O2	1.297 (5)
C9—C10	1.529 (6)	N1—Ni1	1.871 (4)
C10—H10A	0.9600	N2—Ni1	1.870 (4)
C10—H10B	0.9600	Ni1—O1	1.846 (3)
C10—H10C	0.9600	Ni1—O2	1.858 (3)
O1—C1—C6	124.1 (4)	H11A—C11—H11C	109.5
O1—C1—C2	119.5 (4)	H11B—C11—H11C	109.5
C6—C1—C2	116.5 (4)	N2—C12—C9	113.6 (4)
C3—C2—C1	122.3 (4)	N2—C12—H12A	108.8
C3—C2—Cl1	119.0 (3)	C9—C12—H12A	108.8
C1—C2—Cl1	118.7 (3)	N2—C12—H12B	108.8
C2—C3—C4	120.0 (4)	C9—C12—H12B	108.8
C2—C3—H3	120.0	H12A—C12—H12B	107.7
C4—C3—H3	120.0	N2—C13—C14	125.9 (4)
C5—C4—C3	120.1 (4)	N2—C13—H13	117.1
C5—C4—Cl2	120.5 (4)	C14—C13—H13	117.1
C3—C4—Cl2	119.4 (4)	C15—C14—C19	120.9 (4)
C4—C5—C6	120.6 (4)	C15—C14—C13	118.7 (4)
C4—C5—H5	119.7	C19—C14—C13	120.3 (4)
C6—C5—H5	119.7	C16—C15—C14	120.8 (4)
C5—C6—C1	120.5 (4)	C16—C15—H15	119.6
C5—C6—C7	118.5 (4)	C14—C15—H15	119.6
C1—C6—C7	120.8 (4)	C15—C16—C17	120.5 (5)
N1—C7—C6	125.9 (4)	C15—C16—Cl3	120.1 (4)
N1—C7—H7	117.1	C17—C16—Cl3	119.3 (4)
C6—C7—H7	117.1	C18—C17—C16	119.5 (4)
N1—C8—C9	113.0 (4)	C18—C17—H17	120.3
N1—C8—H8A	109.0	C16—C17—H17	120.3
C9—C8—H8A	109.0	C17—C18—C19	122.9 (4)
N1—C8—H8B	109.0	C17—C18—Cl4	118.5 (4)
C9—C8—H8B	109.0	C19—C18—Cl4	118.6 (3)
H8A—C8—H8B	107.8	O2—C19—C18	120.2 (4)
C8—C9—C12	109.4 (4)	O2—C19—C14	124.5 (4)
C8—C9—C11	110.7 (4)	C18—C19—C14	115.3 (4)
C12—C9—C11	108.3 (4)	C7—N1—C8	117.6 (4)
C8—C9—C10	107.9 (4)	C7—N1—Ni1	126.2 (3)
C12—C9—C10	110.9 (4)	C8—N1—Ni1	115.5 (3)
C11—C9—C10	109.6 (4)	C13—N2—C12	117.8 (4)
C9—C10—H10A	109.5	C13—N2—Ni1	125.6 (3)
C9—C10—H10B	109.5	C12—N2—Ni1	115.4 (3)
H10A—C10—H10B	109.5	O1—Ni1—O2	84.50 (12)
C9—C10—H10C	109.5	O1—Ni1—N2	164.78 (14)
H10A—C10—H10C	109.5	O2—Ni1—N2	94.25 (15)
H10B—C10—H10C	109.5	O1—Ni1—N1	93.97 (14)
C9—C11—H11A	109.5	O2—Ni1—N1	165.55 (14)
C9—C11—H11B	109.5	N2—Ni1—N1	90.93 (16)
H11A—C11—H11B	109.5	C1—O1—Ni1	127.5 (3)
C9—C11—H11C	109.5	C19—O2—Ni1	126.2 (3)
O1—C1—C2—C3	179.3 (4)	C17—C18—C19—C14	0.5 (7)
C6—C1—C2—C3	−0.2 (7)	Cl4—C18—C19—C14	178.9 (3)
O1—C1—C2—Cl1	−0.9 (6)	C15—C14—C19—O2	−176.9 (4)
C6—C1—C2—Cl1	179.6 (3)	C13—C14—C19—O2	−1.2 (7)
C1—C2—C3—C4	−1.0 (7)	C15—C14—C19—C18	1.2 (6)
Cl1—C2—C3—C4	179.3 (4)	C13—C14—C19—C18	176.8 (4)
C2—C3—C4—C5	0.7 (7)	C6—C7—N1—C8	−171.3 (4)
C2—C3—C4—Cl2	−178.6 (4)	C6—C7—N1—Ni1	−1.3 (7)
C3—C4—C5—C6	0.6 (7)	C9—C8—N1—C7	−115.1 (5)
Cl2—C4—C5—C6	179.9 (4)	C9—C8—N1—Ni1	73.8 (4)
C4—C5—C6—C1	−1.7 (7)	C14—C13—N2—C12	−172.4 (4)
C4—C5—C6—C7	−177.2 (4)	C14—C13—N2—Ni1	−5.8 (7)
O1—C1—C6—C5	−178.0 (4)	C9—C12—N2—C13	−118.9 (4)
C2—C1—C6—C5	1.5 (6)	C9—C12—N2—Ni1	73.2 (4)
O1—C1—C6—C7	−2.6 (7)	C13—N2—Ni1—O1	−92.3 (7)
C2—C1—C6—C7	176.8 (4)	C12—N2—Ni1—O1	74.5 (7)
C5—C6—C7—N1	−176.0 (4)	C13—N2—Ni1—O2	−7.7 (4)
C1—C6—C7—N1	8.6 (7)	C12—N2—Ni1—O2	159.2 (3)
N1—C8—C9—C12	−37.5 (5)	C13—N2—Ni1—N1	158.8 (4)
N1—C8—C9—C11	81.8 (5)	C12—N2—Ni1—N1	−34.4 (3)
N1—C8—C9—C10	−158.3 (4)	C7—N1—Ni1—O1	−7.7 (4)
C8—C9—C12—N2	−33.1 (5)	C8—N1—Ni1—O1	162.5 (3)
C11—C9—C12—N2	−153.9 (4)	C7—N1—Ni1—O2	−91.0 (7)
C10—C9—C12—N2	85.8 (5)	C8—N1—Ni1—O2	79.2 (6)
N2—C13—C14—C15	−171.2 (5)	C7—N1—Ni1—N2	157.9 (4)
N2—C13—C14—C19	13.0 (7)	C8—N1—Ni1—N2	−31.9 (3)
C19—C14—C15—C16	−2.2 (7)	C6—C1—O1—Ni1	−10.1 (6)
C13—C14—C15—C16	−177.9 (5)	C2—C1—O1—Ni1	170.4 (3)
C14—C15—C16—C17	1.5 (8)	O2—Ni1—O1—C1	178.9 (4)
C14—C15—C16—Cl3	−179.5 (4)	N2—Ni1—O1—C1	−95.1 (7)
C15—C16—C17—C18	0.1 (8)	N1—Ni1—O1—C1	13.3 (4)
Cl3—C16—C17—C18	−178.8 (4)	C18—C19—O2—Ni1	165.5 (3)
C16—C17—C18—C19	−1.2 (7)	C14—C19—O2—Ni1	−16.6 (6)
C16—C17—C18—Cl4	−179.5 (4)	O1—Ni1—O2—C19	−176.6 (4)
C17—C18—C19—O2	178.6 (4)	N2—Ni1—O2—C19	18.6 (4)
Cl4—C18—C19—O2	−3.0 (6)	N1—Ni1—O2—C19	−92.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.97	2.52	3.269 (5)	134
C12—H12A···Cl4ii	0.97	2.80	3.578 (5)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.97	2.52	3.269 (5)	134
C12—H12A⋯Cl4ii	0.97	2.80	3.578 (5)	138

Symmetry codes: (i) ; (ii) .