{4,4′,6,6′-Tetra­chloro-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methanylyl­idene)]}nickel(II)

Kargar, H.; Kia, R.; Abbasian, S.; Tahir, M.N.

doi:10.1107/S1600536812002085

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m193

doi:10.1107/S1600536812002085

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{4,4′,6,6′-Tetrachloro-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]}nickel(II)

Hadi Kargar,^a ^* Reza Kia,^b,^c Saeideh Abbasian ^a and Muhammad Nawaz Tahir ^d ^*

^aDepartment of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, I. R. of IRAN, ^bX-ray Crystallography Lab., 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 8 January 2012; accepted 17 January 2012; online 21 January 2012)

In the title compound, [Ni(C₁₉H₁₆Cl₄N₂O₂)], the Ni^II ion is in a distorted square-planar environment coordinated by two N atoms and two O atoms of the tetradentate ligand. The dihedral angle between the benzene rings is 24.8 (2)°. In the crystal, molecules are linked into chains along the b axis by weak C—H⋯O and C—H⋯Cl interactions. An intermolecular Cl⋯Cl [3.4564 (19) Å] interaction 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_r = 504.85
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.065
wR(F²) = 0.127
S = 1.05
4874 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 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	2.52	3.269 (5)	134
C12—H12A⋯Cl4ⁱⁱ	0.97	2.80	3.578 (5)	138
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y, -z.

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/S1600536812002085/lh5404sup1.cif

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

checkCIF report

Comment top

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with ease of preparation and structural variation (Granovski et al., 1993; Blower et al., (1998). In continuation of our work on the crystal structure of Schiff base metal complexes (Kargar et al., 2012; Kargar et al., 2011; Ghaemi, et al., (2011), we have determined the X-ray structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a Schiff base complex. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structure (Kargar et al., 2012; Kargar et al., 2011; Ghaemi, et al., (2011).

The geometry around the Ni^II ion is a distorted square-plane which is supported by the N₂O₂ donor atoms of the coordinated Schiff base ligand. The dihedral angle between the substituted benzene rings is 24.8 (2)°.

In the crystal, molecules are linked along the b-axis, forming one-dimensional extended chains via intermolecular C—H···O and C—H···Cl interactions (Table 1, Fig. 2). In addition, Cl1···Cl2ⁱⁱⁱ [3.4564 (19)Å; (iii) 1/2 - x, -1/2 + y, -1/2 - z] interactions are present in the crystal structure which are shorter than the sum of the van der Waals radii of Cl atoms [3.50Å]. These also link neighboring molecules along the b-axis (Fig. 3).

Related literature top

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 top

The title compound was synthesized by adding 3,5-dichloro-salicylaldehyde-2,2-dimethyl-1, 3-propanediamine (2 mmol) to a solution of NiCl₂. 6H₂O (2.1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant solution was filtered. Dark-green 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 40% probability displacement ellipsoids.
	Fig. 2. Part of the packing of the title compound showing molecules linked through intermolecular C—H···O and C—H···Cl intearctions (dashed lines). Only the H atoms involved in the interactions are shown.
	Fig. 3. Part of the packing of the title compound viewed along the a -axis, showing molecules linked along the b-axis by intermolecular Cl···Cl intearctions(dashed lines).

{4,4',6,6'-Tetrachloro-2,2'-[2,2-dimethylpropane-1,3- diylbis(nitrilomethanylylidene)]}nickel(II) top

Crystal data top

[Ni(C₁₉H₁₆Cl₄N₂O₂)]	F(000) = 1024
M_r = 504.85	D_x = 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

Data collection top

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

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0401P)² + 1.6535P] where P = (F_o² + 2F_c²)/3
4874 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Ni(C₁₉H₁₆Cl₄N₂O₂)]	V = 2057.0 (2) Å³
M_r = 504.85	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.4019 (8) Å	µ = 1.48 mm⁻¹
b = 8.1883 (6) Å	T = 291 K
c = 20.3945 (13) Å	0.25 × 0.18 × 0.09 mm
β = 96.680 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4874 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2682 reflections with I > 2σ(I)
T_min = 0.694, T_max = 0.871	R_int = 0.090
17449 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.05	Δρ_max = 0.49 e Å⁻³
4874 reflections	Δρ_min = −0.41 e Å⁻³
255 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	0.4518 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₉H₁₆Cl₄N₂O₂)]
M_r	504.85
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	12.4019 (8), 8.1883 (6), 20.3945 (13)
β (°)	96.680 (3)
V (Å³)	2057.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.48
Crystal size (mm)	0.25 × 0.18 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.694, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	17449, 4874, 2682
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.127, 1.05
No. of reflections	4874
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.41

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	2.52	3.269 (5)	134
C12—H12A···Cl4ⁱⁱ	0.97	2.80	3.578 (5)	138

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z.

Acknowledgements

HK and SA thank PNU for the financial support. MNT thanks GC University of Sargodha, Pakistan for the research facility.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Blower, P. J. (1998). Transition Met. Chem., 23, 109–112. CrossRef CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ghaemi, A., Rayati, S., Elahi, E., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, m1445–m1446. Web of Science CSD CrossRef IUCr Journals Google Scholar
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev., 126, 1–69. Google Scholar
Kargar, H., Kia, R., Pahlavani, E. & Tahir, M. N. (2011). Acta Cryst. E67, m941. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kargar, H., Kia, R., Sharafi, Z. & Tahir, M. N. (2012). Acta Cryst. E68, m82. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 2| February 2012| Page m193

doi:10.1107/S1600536812002085

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{4,4′,6,6′-Tetra­chloro-2,2′-[2,2-di­methyl­propane-1,3-diylbis(nitrilo­methanylyl­­idene)]}nickel(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{4,4′,6,6′-Tetrachloro-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]}nickel(II)