{4,4′-Dichloro-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methanyl­ylidene)]diphenolato-κ4O,N,N′,O′}nickel(II)

Kargar, H.; Kia, R.; Pahlavani, E.; Tahir, M.N.

doi:10.1107/S1600536811022732

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m941

doi:10.1107/S1600536811022732

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{4,4′-Dichloro-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]diphenolato-κ⁴O,N,N′,O′}nickel(II)

Hadi Kargar,^a ^* Reza Kia,^b,^c Elham Pahlavani ^a and Muhammad Nawaz Tahir ^d ^*

^aChemistry Department, Payame Noor University, Tehran 19395-4697, I. R. of Iran, ^bX-ray Crystallography Laboratory, Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^dDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: hkargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 3 June 2011; accepted 12 June 2011; online 18 June 2011)

In the title compound, [Ni(C₁₉H₁₈Cl₂N₂O₂)], 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 intermolecular C—H⋯O hydrogen bonds link neighboring molecules into a chain along the a axis. The crystal structure is further stabilized by π–π interactions [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_r = 435.96
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.081
S = 1.02
3354 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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) -x+1, -y, -z+2; (ii) -x+2, -y, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022732/kj2181sup1.cif

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

checkCIF report

Comment top

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with their ease of preparation and structural variations (Granovski et al., 1993). Metal derivatives of the Schiff bases have been studied extensively, and Ni^II and Cu(II) complexes play a major role in both synthetic and structurel research (Elmali et al., 2000; Blower et al., 1998). In continuation of our work on Schiff base ligands and their metal complexes (Fun et al., 2008; Kargar et al., 2008), we determined the X-ray crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises one unit of the Schiff base complex. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the previous structures (Kargar et al., 2008; Rayati et al., 2011). The geometry ground the Ni^II atom is a sligthly distorted square-planar which is coordinated by the N₂O₂ donor atoms of the desired potentially tetradenate Schiff base ligand. The dihedral angle between the mean planes of the coordination plane rings, O1–Ni1–N1 and O2–Ni1–N2, is 9.15 (12)°. The dihedral angle between the mean planes of the two aromatic rings is 3.48 (16)°.

The crystal structure is stabilized by pairs of intermolecular C—H···O hydrogen bonds which link neighboring molecules into a chain along the a-axis (Table 1, Fig. 2) and by π–π interactions [Cg1···Cg2ⁱⁱ = 3.883 (2) Å; Cg1 and Cg2 are the centroids of the C1–C6 and C14–C19 benzene rings].

Related literature top

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 top

The title compound was synthesized by adding bis(5-chlorosalicylaldiminato)-2,3-propanediamine (2 mmol) to a solution of NiCl₂. 6 H₂O (2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant red solution was filtered. Red single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. Packing diagram of the title compound, showing a 1-D infinite chain along the a-axis by the intermolecular C—H···O interactions. The intermolecular interactions are shown as dashed lines. Only the H atoms involved in hydrogen bonding are shown.

{4,4'-Dichloro-2,2'-[2,2-dimethylpropane-1,3- diylbis(nitrilomethanylylidene)]diphenolato- κ⁴O,N,N',O'}nickel(II) top

Crystal data top

[Ni(C₁₉H₁₈Cl₂N₂O₂)]	F(000) = 896
M_r = 435.96	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.024P)² + 0.6017P] where P = (F_o² + 2F_c²)/3
3354 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Ni(C₁₉H₁₈Cl₂N₂O₂)]	V = 1848.16 (14) Å³
M_r = 435.96	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.9781 (3) Å	µ = 1.36 mm⁻¹
b = 23.2517 (11) Å	T = 296 K
c = 11.8395 (5) Å	0.22 × 0.15 × 0.09 mm
β = 105.828 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3354 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2373 reflections with I > 2σ(I)
T_min = 0.755, T_max = 0.888	R_int = 0.062
14131 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
3354 reflections	Δρ_min = −0.29 e Å⁻³
237 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2; (ii) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₉H₁₈Cl₂N₂O₂)]
M_r	435.96
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	6.9781 (3), 23.2517 (11), 11.8395 (5)
β (°)	105.828 (3)
V (Å³)	1848.16 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.36
Crystal size (mm)	0.22 × 0.15 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.755, 0.888
No. of measured, independent and observed [I > 2σ(I)] reflections	14131, 3354, 2373
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.081, 1.02
No. of reflections	3354
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.29

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2; (ii) −x+2, −y, −z+2.

Acknowledgements

HK and EP thank PNU for financial support. RK also thanks the Islamic Azad University. MNT thanks SU University, Pakistan for the research facilities.

References

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