{4,4'-Dichloro-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanyl-ylidene)]diphenolato-κO,N,N',O'}nickel(II).

In the title compound, [Ni(C(19)H(18)Cl(2)N(2)O(2))], the Ni(II) atom shows a slightly distorted square-planar geometry. The dihedral angle between the mean planes of the coordination rings is 9.15 (12)° while the dihedral angle between the mean planes of the two aromatic rings is 3.48 (16)°. In the crystal, pairs of inter-molecular C-H⋯O hydrogen bonds link neighboring mol-ecules into a chain along the a axis. The crystal structure is further stabilized by π-π inter-actions [centroid-centroid distance = 3.883 (2) Å].

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For background to Schiff base metal complexes, see: Granovski et al. (1993 ▶); Blower (1998 ▶); Elmali et al. (2000 ▶). For related structures, see: Fun et al. (2008 ▶); Kargar et al. (2008 ▶); Rayati et al. (2011 ▶).

Experimental

Crystal data

[Ni(C19H18Cl2N2O2)]

M = 435.96

Monoclinic,

a = 6.9781 (3) Å

b = 23.2517 (11) Å

c = 11.8395 (5) Å

β = 105.828 (3)°

V = 1848.16 (14) Å3

Z = 4

Mo Kα radiation

μ = 1.36 mm−1

T = 296 K

0.22 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.755, T max = 0.888

14131 measured reflections

3354 independent reflections

2373 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.081

S = 1.02

3354 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.29 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/S1600536811022732/kj2181sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022732/kj2181Isup2.hkl

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

[Ni(C19H18Cl2N2O2)]	F(000) = 896
Mr = 435.96	Dx = 1.567 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2545 reflections
a = 6.9781 (3) Å	θ = 2.5–27.4°
b = 23.2517 (11) Å	µ = 1.36 mm−1
c = 11.8395 (5) Å	T = 296 K
β = 105.828 (3)°	Block, red
V = 1848.16 (14) Å3	0.22 × 0.15 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3354 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 25.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.755, Tmax = 0.888	k = −27→27
14131 measured reflections	l = −14→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.024P)2 + 0.6017P] where P = (Fo2 + 2Fc2)/3
3354 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.29 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	0.6314 (4)	−0.09890 (13)	0.9031 (3)	0.0331 (7)
C2	0.6332 (5)	−0.15815 (14)	0.9279 (3)	0.0418 (8)
H2	0.6782	−0.1704	1.0054	0.050*
C3	0.5704 (5)	−0.19826 (14)	0.8410 (3)	0.0445 (9)
H3	0.5757	−0.2372	0.8594	0.053*
C4	0.4986 (5)	−0.18048 (14)	0.7248 (3)	0.0437 (9)
C5	0.4879 (5)	−0.12370 (14)	0.6975 (3)	0.0391 (8)
H5	0.4359	−0.1122	0.6199	0.047*
C6	0.5545 (4)	−0.08216 (13)	0.7852 (3)	0.0325 (7)
C7	0.5194 (4)	−0.02263 (13)	0.7560 (3)	0.0352 (8)
H7	0.4456	−0.0141	0.6798	0.042*
C8	0.4941 (4)	0.07694 (13)	0.7879 (3)	0.0374 (8)
H8A	0.4334	0.0915	0.8468	0.045*
H8B	0.3897	0.0728	0.7151	0.045*
C9	0.6463 (5)	0.12107 (13)	0.7696 (3)	0.0373 (8)
C10	0.6756 (5)	0.11497 (16)	0.6468 (3)	0.0580 (11)
H10A	0.7827	0.1395	0.6401	0.087*
H10B	0.5554	0.1259	0.5892	0.087*
H10C	0.7071	0.0757	0.6341	0.087*
C11	0.5692 (5)	0.18114 (14)	0.7853 (3)	0.0535 (10)
H11A	0.5712	0.1867	0.8659	0.080*
H11B	0.4353	0.1851	0.7364	0.080*
H11C	0.6527	0.2094	0.7632	0.080*
C12	0.8481 (5)	0.11072 (14)	0.8595 (3)	0.0378 (8)
H12A	0.9217	0.0823	0.8283	0.045*
H12B	0.9240	0.1462	0.8704	0.045*
C13	0.8949 (4)	0.12409 (13)	1.0628 (3)	0.0351 (8)
H13	0.9212	0.1621	1.0476	0.042*
C14	0.9299 (4)	0.10732 (14)	1.1837 (3)	0.0338 (8)
C15	0.9916 (4)	0.14918 (15)	1.2715 (3)	0.0402 (8)
H15	0.9932	0.1877	1.2509	0.048*
C16	1.0493 (5)	0.13369 (16)	1.3869 (3)	0.0453 (9)
C17	1.0546 (5)	0.07581 (17)	1.4183 (3)	0.0490 (9)
H17	1.0970	0.0654	1.4970	0.059*
C18	0.9979 (5)	0.03433 (15)	1.3341 (3)	0.0450 (9)
H18	1.0042	−0.0041	1.3565	0.054*
C19	0.9299 (4)	0.04858 (14)	1.2136 (3)	0.0352 (8)
Ni1	0.74438 (6)	0.014738 (17)	0.97955 (3)	0.03310 (13)
N1	0.5800 (4)	0.02007 (11)	0.8250 (2)	0.0333 (6)
N2	0.8306 (4)	0.09081 (11)	0.9745 (2)	0.0316 (6)
O1	0.6943 (3)	−0.06300 (9)	0.98952 (18)	0.0407 (6)
O2	0.8753 (3)	0.00713 (9)	1.13730 (19)	0.0426 (6)
Cl1	0.41277 (16)	−0.23188 (4)	0.61498 (9)	0.0684 (3)
Cl2	1.12556 (16)	0.18517 (5)	1.49697 (9)	0.0697 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0326 (18)	0.0283 (18)	0.040 (2)	0.0005 (15)	0.0131 (15)	0.0023 (16)
C2	0.047 (2)	0.037 (2)	0.044 (2)	0.0008 (17)	0.0160 (17)	0.0098 (17)
C3	0.046 (2)	0.028 (2)	0.061 (3)	0.0006 (16)	0.0182 (18)	0.0039 (18)
C4	0.040 (2)	0.033 (2)	0.056 (2)	−0.0042 (16)	0.0111 (17)	−0.0100 (18)
C5	0.039 (2)	0.040 (2)	0.038 (2)	0.0021 (16)	0.0085 (15)	0.0009 (16)
C6	0.0307 (18)	0.0297 (18)	0.039 (2)	−0.0019 (15)	0.0129 (15)	0.0005 (15)
C7	0.0370 (19)	0.037 (2)	0.0315 (18)	−0.0003 (16)	0.0098 (14)	0.0040 (15)
C8	0.0385 (19)	0.035 (2)	0.0336 (19)	0.0068 (16)	0.0021 (15)	0.0027 (15)
C9	0.048 (2)	0.033 (2)	0.0322 (19)	0.0043 (16)	0.0130 (16)	0.0067 (15)
C10	0.070 (3)	0.065 (3)	0.040 (2)	0.002 (2)	0.0174 (19)	0.011 (2)
C11	0.063 (3)	0.037 (2)	0.056 (2)	0.0097 (19)	0.0098 (19)	0.0074 (18)
C12	0.048 (2)	0.034 (2)	0.0355 (19)	−0.0008 (16)	0.0196 (16)	0.0063 (15)
C13	0.0365 (19)	0.0305 (19)	0.039 (2)	0.0028 (15)	0.0108 (15)	0.0045 (16)
C14	0.0273 (17)	0.038 (2)	0.0367 (19)	0.0046 (15)	0.0089 (14)	0.0038 (16)
C15	0.038 (2)	0.042 (2)	0.040 (2)	0.0016 (17)	0.0097 (16)	0.0020 (17)
C16	0.038 (2)	0.057 (3)	0.040 (2)	−0.0024 (18)	0.0091 (16)	−0.0106 (18)
C17	0.048 (2)	0.067 (3)	0.031 (2)	−0.003 (2)	0.0074 (16)	0.0037 (19)
C18	0.048 (2)	0.047 (2)	0.039 (2)	0.0015 (18)	0.0094 (16)	0.0102 (18)
C19	0.0294 (18)	0.042 (2)	0.0334 (19)	−0.0013 (16)	0.0064 (14)	0.0018 (16)
Ni1	0.0394 (2)	0.0284 (2)	0.0311 (2)	0.0014 (2)	0.00896 (17)	0.00520 (19)
N1	0.0383 (15)	0.0279 (15)	0.0336 (15)	0.0024 (13)	0.0094 (12)	0.0069 (12)
N2	0.0363 (15)	0.0295 (15)	0.0292 (15)	0.0029 (12)	0.0095 (12)	0.0054 (12)
O1	0.0572 (15)	0.0327 (13)	0.0316 (13)	−0.0017 (11)	0.0111 (11)	0.0057 (11)
O2	0.0556 (15)	0.0330 (14)	0.0354 (13)	0.0010 (11)	0.0061 (10)	0.0073 (11)
Cl1	0.0813 (8)	0.0419 (6)	0.0727 (7)	−0.0029 (5)	0.0050 (6)	−0.0173 (5)
Cl2	0.0797 (8)	0.0730 (8)	0.0478 (6)	−0.0004 (6)	0.0027 (5)	−0.0190 (5)

C1—O1	1.301 (3)	C11—H11A	0.9600
C1—C6	1.407 (4)	C11—H11B	0.9600
C1—C2	1.408 (4)	C11—H11C	0.9600
C2—C3	1.369 (4)	C12—N2	1.474 (3)
C2—H2	0.9300	C12—H12A	0.9700
C3—C4	1.392 (5)	C12—H12B	0.9700
C3—H3	0.9300	C13—N2	1.279 (4)
C4—C5	1.357 (4)	C13—C14	1.440 (4)
C4—Cl1	1.748 (3)	C13—H13	0.9300
C5—C6	1.401 (4)	C14—C15	1.403 (4)
C5—H5	0.9300	C14—C19	1.411 (4)
C6—C7	1.431 (4)	C15—C16	1.363 (4)
C7—N1	1.282 (4)	C15—H15	0.9300
C7—H7	0.9300	C16—C17	1.394 (5)
C8—N1	1.469 (4)	C16—Cl2	1.742 (3)
C8—C9	1.534 (4)	C17—C18	1.366 (4)
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700	C18—C19	1.414 (4)
C9—C11	1.526 (4)	C18—H18	0.9300
C9—C10	1.529 (4)	C19—O2	1.305 (4)
C9—C12	1.535 (4)	Ni1—O2	1.850 (2)
C10—H10A	0.9600	Ni1—O1	1.851 (2)
C10—H10B	0.9600	Ni1—N2	1.874 (2)
C10—H10C	0.9600	Ni1—N1	1.880 (2)
O1—C1—C6	124.0 (3)	H11A—C11—H11C	109.5
O1—C1—C2	118.8 (3)	H11B—C11—H11C	109.5
C6—C1—C2	117.2 (3)	N2—C12—C9	113.5 (2)
C3—C2—C1	121.8 (3)	N2—C12—H12A	108.9
C3—C2—H2	119.1	C9—C12—H12A	108.9
C1—C2—H2	119.1	N2—C12—H12B	108.9
C2—C3—C4	119.7 (3)	C9—C12—H12B	108.9
C2—C3—H3	120.1	H12A—C12—H12B	107.7
C4—C3—H3	120.1	N2—C13—C14	125.1 (3)
C5—C4—C3	120.4 (3)	N2—C13—H13	117.4
C5—C4—Cl1	120.2 (3)	C14—C13—H13	117.4
C3—C4—Cl1	119.3 (3)	C15—C14—C19	120.4 (3)
C4—C5—C6	120.6 (3)	C15—C14—C13	118.9 (3)
C4—C5—H5	119.7	C19—C14—C13	120.0 (3)
C6—C5—H5	119.7	C16—C15—C14	120.4 (3)
C5—C6—C1	120.3 (3)	C16—C15—H15	119.8
C5—C6—C7	119.2 (3)	C14—C15—H15	119.8
C1—C6—C7	120.0 (3)	C15—C16—C17	120.1 (3)
N1—C7—C6	126.2 (3)	C15—C16—Cl2	121.0 (3)
N1—C7—H7	116.9	C17—C16—Cl2	118.9 (3)
C6—C7—H7	116.9	C18—C17—C16	120.4 (3)
N1—C8—C9	113.8 (2)	C18—C17—H17	119.8
N1—C8—H8A	108.8	C16—C17—H17	119.8
C9—C8—H8A	108.8	C17—C18—C19	121.4 (3)
N1—C8—H8B	108.8	C17—C18—H18	119.3
C9—C8—H8B	108.8	C19—C18—H18	119.3
H8A—C8—H8B	107.7	O2—C19—C14	124.1 (3)
C11—C9—C10	110.1 (3)	O2—C19—C18	118.7 (3)
C11—C9—C8	108.3 (3)	C14—C19—C18	117.2 (3)
C10—C9—C8	110.5 (3)	O2—Ni1—O1	83.80 (9)
C11—C9—C12	110.3 (3)	O2—Ni1—N2	92.76 (10)
C10—C9—C12	108.0 (3)	O1—Ni1—N2	172.47 (10)
C8—C9—C12	109.7 (2)	O2—Ni1—N1	172.29 (10)
C9—C10—H10A	109.5	O1—Ni1—N1	92.91 (10)
C9—C10—H10B	109.5	N2—Ni1—N1	91.30 (11)
H10A—C10—H10B	109.5	C7—N1—C8	118.0 (3)
C9—C10—H10C	109.5	C7—N1—Ni1	125.2 (2)
H10A—C10—H10C	109.5	C8—N1—Ni1	116.2 (2)
H10B—C10—H10C	109.5	C13—N2—C12	117.7 (3)
C9—C11—H11A	109.5	C13—N2—Ni1	126.1 (2)
C9—C11—H11B	109.5	C12—N2—Ni1	115.7 (2)
H11A—C11—H11B	109.5	C1—O1—Ni1	127.3 (2)
C9—C11—H11C	109.5	C19—O2—Ni1	126.8 (2)
O1—C1—C2—C3	−179.5 (3)	C15—C14—C19—O2	−179.8 (3)
C6—C1—C2—C3	2.5 (4)	C13—C14—C19—O2	−9.0 (4)
C1—C2—C3—C4	−1.4 (5)	C15—C14—C19—C18	−1.3 (4)
C2—C3—C4—C5	−0.9 (5)	C13—C14—C19—C18	169.6 (3)
C2—C3—C4—Cl1	−178.3 (2)	C17—C18—C19—O2	−179.1 (3)
C3—C4—C5—C6	2.0 (5)	C17—C18—C19—C14	2.3 (5)
Cl1—C4—C5—C6	179.3 (2)	C6—C7—N1—C8	−167.1 (3)
C4—C5—C6—C1	−0.7 (5)	C6—C7—N1—Ni1	4.1 (4)
C4—C5—C6—C7	−172.5 (3)	C9—C8—N1—C7	−116.4 (3)
O1—C1—C6—C5	−179.3 (3)	C9—C8—N1—Ni1	71.7 (3)
C2—C1—C6—C5	−1.5 (4)	O1—Ni1—N1—C7	−17.0 (2)
O1—C1—C6—C7	−7.6 (4)	N2—Ni1—N1—C7	156.7 (2)
C2—C1—C6—C7	170.2 (3)	O1—Ni1—N1—C8	154.3 (2)
C5—C6—C7—N1	−176.3 (3)	N2—Ni1—N1—C8	−32.0 (2)
C1—C6—C7—N1	11.9 (5)	C14—C13—N2—C12	−165.8 (3)
N1—C8—C9—C11	−155.3 (3)	C14—C13—N2—Ni1	6.0 (4)
N1—C8—C9—C10	84.0 (3)	C9—C12—N2—C13	−114.6 (3)
N1—C8—C9—C12	−34.9 (3)	C9—C12—N2—Ni1	72.8 (3)
C11—C9—C12—N2	84.4 (3)	O2—Ni1—N2—C13	−19.4 (3)
C10—C9—C12—N2	−155.2 (3)	N1—Ni1—N2—C13	154.1 (3)
C8—C9—C12—N2	−34.8 (4)	O2—Ni1—N2—C12	152.6 (2)
N2—C13—C14—C15	−176.9 (3)	N1—Ni1—N2—C12	−34.0 (2)
N2—C13—C14—C19	12.1 (5)	C6—C1—O1—Ni1	−12.5 (4)
C19—C14—C15—C16	−1.1 (4)	C2—C1—O1—Ni1	169.7 (2)
C13—C14—C15—C16	−172.0 (3)	O2—Ni1—O1—C1	−165.5 (2)
C14—C15—C16—C17	2.5 (5)	N1—Ni1—O1—C1	21.5 (2)
C14—C15—C16—Cl2	−179.8 (2)	C14—C19—O2—Ni1	−12.1 (4)
C15—C16—C17—C18	−1.5 (5)	C18—C19—O2—Ni1	169.4 (2)
Cl2—C16—C17—C18	−179.3 (3)	O1—Ni1—O2—C19	−164.2 (2)
C16—C17—C18—C19	−0.9 (5)	N2—Ni1—O2—C19	22.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.97	2.44	3.266 (4)	143
C12—H12A···O2ii	0.97	2.49	3.346 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.97	2.44	3.266 (4)	143
C12—H12A⋯O2ii	0.97	2.49	3.346 (4)	148

Symmetry codes: (i) ; (ii) .