{4,4′-Dimethyl-2,2′-[(2,2-dimethyl­propane-1,3-di­yl)bis­(nitrilo­methanylyl­idene)]diphenolato}nickel(II) monohydrate

Kargar, H.; Kia, R.; Sharafi, Z.; Tahir, M.N.

doi:10.1107/S1600536811054262

metal-organic compounds

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Volume 68| Part 1| January 2012| Page m82

doi:10.1107/S1600536811054262

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{4,4′-Dimethyl-2,2′-[(2,2-dimethylpropane-1,3-diyl)bis(nitrilomethanylylidene)]diphenolato}nickel(II) monohydrate

Hadi Kargar,^a ^* Reza Kia,^b,^c Zahra Sharafi ^d and Muhammad Nawaz Tahir ^e ^*

^aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, 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, ^dDepartment of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran, and ^eDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: hkargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 11 December 2011; accepted 16 December 2011; online 23 December 2011)

In the title compound, [Ni(C₂₁H₂₄N₂O₂)]·H₂O, both the complex molecule and the water molecule lie on a twofold rotation axis. The Ni^II ion is coordinated in a distorted square-planar geometry by the tetradentate ligand. The dihedral angle between the two symmetry-related benzene rings is 47.12 (8)°. In the crystal, pairs of symmetry-related O—H⋯O hydrogen bonds form R₂²(6) ring motifs. In addition, there are weak intermolecular C—H⋯O hydrogen bonds, and π–π stacking interactions with a centroid–centroid distance of 3.4760 (8) Å.

Related literature

For related structures, see for example: Fun et al. (2008 ); Kargar et al. (2008 , 2011 ); Rayati et al. (2011 ); Kia et al. (2010 ). For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

[Ni(C₂₁H₂₄N₂O₂)]·H₂O
M_r = 413.15
Monoclinic, C 2/c
a = 13.3333 (4) Å
b = 15.9424 (5) Å
c = 9.9965 (3) Å
β = 104.736 (1)°
V = 2055.01 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 296 K
0.25 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.794, T_max = 0.927
17468 measured reflections
2557 independent reflections
2131 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.083
S = 1.06
2557 reflections
125 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O1ⁱ	0.98	1.92	2.781 (2)	145
C3—H3A⋯O1Wⁱⁱ	0.93	2.55	3.477 (2)	173
Symmetry codes: (i) $[-x, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811054262/lh5396sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054262/lh5396Isup2.hkl

checkCIF report

Comment top

In continuation of our work on the crystal structures of a Schiff base ligands and complexes (Fun et al., 2008; Kargar et al., 2008,2011; Rayati et al., 2011; Kia et al., 2010), we have determined the X-ray structure of the title compound.

The molecular structure of the title compound is ahown in Fig. 1. The asymmetric unit comprises half of Schiff base complex and half a water molecule. The Ni^II ion, the central carbon atom of the diamine segment (C10) and the O atom of water molecule lie on a two-fold rotation axis. The coordination geometry of Ni1 is distorted square-planar formed by the tetradentate ligand. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to related structures (Fun et al. 2008; Kargar et al. 2008; Rayati et al., 2011). The dihedral angle between the two symmetry related benzene rings is 47.12 (8)°. A pair of symmetry related intermolecular O—H···O hydrogen bonds form an R²₂(6) ring motif (Bernstein et al., 1995). In the crystal, molecules are linked through weak intermolecular C—H···O interactions. The crystal structure is further stabilized by intermolecular π–π interactions [Cg1···Cg1ⁱⁱⁱ = 3.4760 (8)Å; (iii) -x, 1 - y, 1 - z; Cg1 is the centroid of the Ni1/O1/C1/C6/C8/N1 ring].

Related literature top

For related structures, see for example: Fun et al. (2008); Kargar et al. (2008, 2011); Rayati et al. (2011); Kia et al. (2010). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by adding bis(5-methylsalicylaldehyde)-2,2-dimethyl-1,3-propanediimine (2 mmol) to a solution of nickel(II) chloride hexahydrate (2.1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from an ethanol solution of the title compound by slow evaporation of the solvent 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).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoids. The dashed lines show hydrogen bonds [symmetry code: (A) -x, y, -z+1/2].
	Fig. 2. A partial packing diagram of the title compound viewed approximately along the c-axis showing molecules linked through intermolecular hydrogen bonds (dashed lines). Only the H atoms involved in the interactions are shown.

{4,4'-Dimethyl-2,2'-[(2,2-dimethylpropane-1,3- diyl)bis(nitrilomethanylylidene)]diphenolato}nickel(II) monohydrate top

Crystal data top

[Ni(C₂₁H₂₄N₂O₂)]·H₂O	F(000) = 872
M_r = 413.15	D_x = 1.335 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3245 reflections
a = 13.3333 (4) Å	θ = 2.8–27.8°
b = 15.9424 (5) Å	µ = 0.97 mm⁻¹
c = 9.9965 (3) Å	T = 296 K
β = 104.736 (1)°	Block, red
V = 2055.01 (11) Å³	0.25 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2557 independent reflections
Radiation source: fine-focus sealed tube	2131 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→16
T_min = 0.794, T_max = 0.927	k = −21→21
17468 measured reflections	l = −13→13

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0485P)²] where P = (F_o² + 2F_c²)/3
2557 reflections	(Δ/σ)_max < 0.001
125 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Ni(C₂₁H₂₄N₂O₂)]·H₂O	V = 2055.01 (11) Å³
M_r = 413.15	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 13.3333 (4) Å	µ = 0.97 mm⁻¹
b = 15.9424 (5) Å	T = 296 K
c = 9.9965 (3) Å	0.25 × 0.12 × 0.08 mm
β = 104.736 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2557 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2131 reflections with I > 2σ(I)
T_min = 0.794, T_max = 0.927	R_int = 0.040
17468 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.06	Δρ_max = 0.21 e Å⁻³
2557 reflections	Δρ_min = −0.31 e Å⁻³
125 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
Ni1	0.0000	0.489837 (15)	0.2500	0.03589 (11)
O1	0.09186 (9)	0.57316 (6)	0.34800 (11)	0.0457 (3)
N1	0.04523 (10)	0.40475 (8)	0.39178 (12)	0.0414 (3)
C1	0.16634 (12)	0.56212 (9)	0.46203 (15)	0.0401 (3)
C2	0.23779 (14)	0.62692 (10)	0.50786 (17)	0.0497 (4)
H2A	0.2346	0.6747	0.4537	0.060*
C3	0.31279 (14)	0.62162 (12)	0.63132 (18)	0.0567 (5)
H3A	0.3589	0.6660	0.6581	0.068*
C4	0.32147 (14)	0.55163 (13)	0.71719 (17)	0.0550 (4)
C5	0.25490 (14)	0.48675 (11)	0.67168 (18)	0.0487 (4)
H5A	0.2604	0.4390	0.7265	0.058*
C6	0.17758 (13)	0.48878 (9)	0.54427 (17)	0.0410 (3)
C7	0.40114 (17)	0.54821 (18)	0.85526 (19)	0.0817 (7)
H7A	0.4556	0.5101	0.8494	0.123*
H7B	0.3687	0.5292	0.9252	0.123*
H7C	0.4297	0.6031	0.8788	0.123*
C8	0.11388 (13)	0.41566 (10)	0.50691 (15)	0.0431 (4)
H8A	0.1230	0.3725	0.5714	0.052*
C9	−0.01669 (14)	0.32780 (10)	0.36982 (16)	0.0488 (4)
H9A	−0.0895	0.3426	0.3512	0.059*
H9B	0.0006	0.2949	0.4542	0.059*
C10	0.0000	0.27358 (15)	0.2500	0.0564 (7)
C11	0.0973 (2)	0.21930 (15)	0.2981 (2)	0.1038 (9)
H11A	0.1569	0.2548	0.3287	0.156*
H11B	0.1057	0.1851	0.2226	0.156*
H11C	0.0903	0.1840	0.3729	0.156*
O1W	0.0000	0.72531 (12)	0.2500	0.0992 (8)
H1	−0.0556	0.6878	0.2007	0.149*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03715 (18)	0.03024 (16)	0.03666 (16)	0.000	0.00274 (11)	0.000
O1	0.0462 (7)	0.0353 (6)	0.0472 (6)	−0.0002 (5)	−0.0032 (5)	0.0020 (5)
N1	0.0448 (8)	0.0367 (7)	0.0424 (7)	−0.0023 (6)	0.0110 (6)	0.0012 (5)
C1	0.0364 (8)	0.0408 (8)	0.0418 (8)	0.0035 (6)	0.0075 (6)	−0.0040 (6)
C2	0.0470 (10)	0.0449 (9)	0.0540 (9)	−0.0035 (7)	0.0069 (8)	−0.0022 (7)
C3	0.0434 (10)	0.0635 (12)	0.0586 (10)	−0.0101 (8)	0.0047 (8)	−0.0118 (9)
C4	0.0391 (10)	0.0794 (13)	0.0432 (9)	−0.0003 (9)	0.0042 (7)	−0.0047 (9)
C5	0.0428 (10)	0.0604 (11)	0.0413 (8)	0.0055 (8)	0.0076 (7)	0.0051 (7)
C6	0.0373 (9)	0.0449 (9)	0.0390 (8)	0.0040 (7)	0.0065 (7)	−0.0010 (6)
C7	0.0590 (14)	0.121 (2)	0.0537 (11)	−0.0122 (13)	−0.0074 (10)	−0.0005 (12)
C8	0.0472 (10)	0.0411 (8)	0.0408 (8)	0.0029 (7)	0.0109 (7)	0.0055 (6)
C9	0.0603 (11)	0.0394 (9)	0.0494 (9)	−0.0103 (8)	0.0189 (8)	0.0006 (7)
C10	0.0806 (19)	0.0355 (12)	0.0563 (14)	0.000	0.0236 (14)	0.000
C11	0.159 (3)	0.0726 (15)	0.0929 (16)	0.0629 (16)	0.0553 (17)	0.0332 (13)
O1W	0.1069 (18)	0.0426 (11)	0.1201 (18)	0.000	−0.0225 (15)	0.000

Geometric parameters (Å, º) top

Ni1—O1	1.901 (1)	C5—H5A	0.9300
Ni1—O1ⁱ	1.9010 (10)	C6—C8	1.435 (2)
Ni1—N1ⁱ	1.9436 (12)	C7—H7A	0.9600
Ni1—N1	1.9436 (12)	C7—H7B	0.9600
O1—C1	1.3194 (17)	C7—H7C	0.9600
N1—C8	1.2870 (19)	C8—H8A	0.9300
N1—C9	1.4638 (19)	C9—C10	1.539 (2)
C1—C2	1.401 (2)	C9—H9A	0.9700
C1—C6	1.415 (2)	C9—H9B	0.9700
C2—C3	1.379 (2)	C10—C11	1.532 (2)
C2—H2A	0.9300	C10—C11ⁱ	1.532 (2)
C3—C4	1.394 (3)	C10—C9ⁱ	1.539 (2)
C3—H3A	0.9300	C11—H11A	0.9600
C4—C5	1.364 (3)	C11—H11B	0.9600
C4—C7	1.513 (2)	C11—H11C	0.9600
C5—C6	1.421 (2)	O1W—H1	0.9818

O1—Ni1—O1ⁱ	91.34 (6)	C4—C7—H7A	109.5
O1—Ni1—N1ⁱ	154.58 (6)	C4—C7—H7B	109.5
O1ⁱ—Ni1—N1ⁱ	94.14 (5)	H7A—C7—H7B	109.5
O1—Ni1—N1	94.14 (5)	C4—C7—H7C	109.5
O1ⁱ—Ni1—N1	154.58 (6)	H7A—C7—H7C	109.5
N1ⁱ—Ni1—N1	91.48 (7)	H7B—C7—H7C	109.5
C1—O1—Ni1	126.63 (9)	N1—C8—C6	125.58 (15)
C8—N1—C9	119.54 (13)	N1—C8—H8A	117.2
C8—N1—Ni1	125.16 (11)	C6—C8—H8A	117.2
C9—N1—Ni1	114.64 (10)	N1—C9—C10	113.57 (13)
O1—C1—C2	118.94 (14)	N1—C9—H9A	108.9
O1—C1—C6	123.87 (14)	C10—C9—H9A	108.9
C2—C1—C6	117.16 (15)	N1—C9—H9B	108.9
C3—C2—C1	121.69 (16)	C10—C9—H9B	108.9
C3—C2—H2A	119.2	H9A—C9—H9B	107.7
C1—C2—H2A	119.2	C11—C10—C11ⁱ	111.2 (3)
C2—C3—C4	121.84 (17)	C11—C10—C9ⁱ	106.43 (11)
C2—C3—H3A	119.1	C11ⁱ—C10—C9ⁱ	110.61 (11)
C4—C3—H3A	119.1	C11—C10—C9	110.61 (11)
C5—C4—C3	117.16 (16)	C11ⁱ—C10—C9	106.43 (11)
C5—C4—C7	121.55 (19)	C9ⁱ—C10—C9	111.63 (18)
C3—C4—C7	121.28 (19)	C10—C11—H11A	109.5
C4—C5—C6	122.98 (17)	C10—C11—H11B	109.5
C4—C5—H5A	118.5	H11A—C11—H11B	109.5
C6—C5—H5A	118.5	C10—C11—H11C	109.5
C1—C6—C5	119.02 (15)	H11A—C11—H11C	109.5
C1—C6—C8	123.49 (15)	H11B—C11—H11C	109.5
C5—C6—C8	117.48 (14)

O1ⁱ—Ni1—O1—C1	163.48 (15)	C7—C4—C5—C6	178.41 (17)
N1ⁱ—Ni1—O1—C1	−93.95 (16)	O1—C1—C6—C5	−174.24 (15)
N1—Ni1—O1—C1	8.32 (13)	C2—C1—C6—C5	4.2 (2)
O1—Ni1—N1—C8	1.34 (13)	O1—C1—C6—C8	5.0 (2)
O1ⁱ—Ni1—N1—C8	−100.61 (16)	C2—C1—C6—C8	−176.58 (15)
N1ⁱ—Ni1—N1—C8	156.53 (16)	C4—C5—C6—C1	−2.0 (3)
O1—Ni1—N1—C9	171.99 (11)	C4—C5—C6—C8	178.70 (16)
O1ⁱ—Ni1—N1—C9	70.04 (15)	C9—N1—C8—C6	−177.90 (15)
N1ⁱ—Ni1—N1—C9	−32.82 (8)	Ni1—N1—C8—C6	−7.7 (2)
Ni1—O1—C1—C2	169.47 (11)	C1—C6—C8—N1	5.6 (3)
Ni1—O1—C1—C6	−12.1 (2)	C5—C6—C8—N1	−175.14 (16)
O1—C1—C2—C3	175.28 (15)	C8—N1—C9—C10	−117.17 (16)
C6—C1—C2—C3	−3.2 (2)	Ni1—N1—C9—C10	71.61 (15)
C1—C2—C3—C4	−0.1 (3)	N1—C9—C10—C11	82.3 (2)
C2—C3—C4—C5	2.4 (3)	N1—C9—C10—C11ⁱ	−156.78 (16)
C2—C3—C4—C7	−177.33 (18)	N1—C9—C10—C9ⁱ	−36.00 (9)
C3—C4—C5—C6	−1.3 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O1ⁱ	0.98	1.92	2.781 (2)	145
C3—H3A···O1Wⁱⁱ	0.93	2.55	3.477 (2)	173

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₂₁H₂₄N₂O₂)]·H₂O
M_r	413.15
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	13.3333 (4), 15.9424 (5), 9.9965 (3)
β (°)	104.736 (1)
V (Å³)	2055.01 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.25 × 0.12 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.794, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	17468, 2557, 2131
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.083, 1.06
No. of reflections	2557
No. of parameters	125
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.31

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O1ⁱ	0.98	1.92	2.781 (2)	145
C3—H3A···O1Wⁱⁱ	0.93	2.55	3.477 (2)	173

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, −y+3/2, −z+1.

Acknowledgements

HK thanks PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for research facilities.

References

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page m82

doi:10.1107/S1600536811054262

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

{4,4′-Di­methyl-2,2′-[(2,2-di­methyl­propane-1,3-di­yl)bis­­(nitrilo­methanylyl­­idene)]diphenolato}nickel(II) monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{4,4′-Dimethyl-2,2′-[(2,2-dimethylpropane-1,3-diyl)bis(nitrilomethanylylidene)]diphenolato}nickel(II) monohydrate