Crystal structure of bis­{2-[(E)-(4-meth­oxy­lbenz­yl)imino­meth­yl]phenolato-κ2N,O1}nickel(II)

Bahron, H.; Tajuddin, A.M.; Ibrahim, W.N.W.; Fun, H.-K.; Chantrapromma, S.

doi:10.1107/S160053681401650X

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Pages 104-106

doi:10.1107/S160053681401650X

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Crystal structure of bis{2-[(E)-(4-methoxylbenzyl)iminomethyl]phenolato-κ²N,O¹}nickel(II)

Hadariah Bahron,^a,^b Amalina Mohd Tajuddin,^a Wan Nazihah Wan Ibrahim,^a,^b Hoong-Kun Fun ^c,^d ^*‡ and Suchada Chantrapromma ^e §

^aFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, ^bDDH CoRe, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^dDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^eDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

Edited by J. Simpson, University of Otago, New Zealand (Received 26 June 2014; accepted 16 July 2014; online 23 July 2014)

The asymmetric unit of the title compound, [Ni(C₁₅H₁₄NO₂)₂], comprises an Ni^II cation, lying on an inversion centre, and a Schiff base anion that acts as a bidentate ligand. The Ni^II cation is in a square-planar coordination environment binding to the imine N and phenolate O atoms of the two Schiff base ligands. The N- and O-donor atoms of the two ligands are mutually trans, with Ni—N and Ni—O bond lengths of 1.9191 (11) and 1.8407 (9) Å, respectively. The plane of the methoxybenzene ring makes a dihedral angle of 84.92 (6)° with that of the phenolate ring. In the crystal, molecules are linked into screw chains by weak C—H⋯O hydrogen bonds. Additional C—H⋯O hydrogen bonds, together with C—H⋯π contacts, arrange the molecules into sheets parallel to the ac plane.

Keywords: crystal structure; nickel(II) complex; NO donors; Schiff base.

CCDC reference: 1014286

1. Chemical context

The title compound, bis{2-[(E)-(4-methoxylbenzyl)iminomethyl]phenolato-κ²N,O¹}nickel(II), (I), is related to bis{2-[1-(benzylimino)ethyl]phenolato}palladium(II) (Mohd Tajuddin et al., 2010 ) in terms of the geometry around the metal centre. However, we have extended our investigation to include a nickel compound with a Schiff base ligand that has a 4-methoxy substituent on the phenyl ring of the benzyl unit bound to the imine N atom (Fig. 1).

Figure 1
The molecular structure of (I)

, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The symmetry-related Schiff base ligand is generated by the symmetry code (−x + 1, −y, −z + 1).

2. Structural commentary

The asymmetric unit of (I) consists of an Ni^II cation that lies on an inversion centre and a Schiff base anion that functions as a bidentate ligand (Fig. 1). The N₂O₂ donor set of the chelating Schiff base ligands has the N1 and O1 donor atoms mutually trans, in a distorted square-planar coordination geometry, with O1—Ni1—N1 = 92.30 (4)° and O1—Ni1—N1ⁱ = 87.70 (4)° [symmetry code: (i) −x + 1, −y, −z + 1] and a maximum deviation from the NiN₂O₂ least-squares plane of 0.731 (1) Å for the N1 atom. The Ni1—N1 and Ni1—O1 bond lengths in the N₂O₂ coordination plane are 1.9191 (11) and 1.8407 (9) Å, respectively. These are similar to those observed in the other closely related Ni^II complexes with N₂O₂-coordinating Schiff base ligands (Bahron et al., 2011 ; Mohd Tajuddin et al., 2010). Other bond lengths and angles observed in the structure are also normal. The methoxy substituent is coplanar with the ring to which it is bound, the C15—O2—C12—C13 torsion angle being 3.93 (2)°. The plane of the methoxybenzene ring (C9–C14) makes a dihedral angle of 84.92 (6)° with that of the phenolate benzene ring (C1–C6). A weak intramolecular C14—H14⋯O1 contact is also observed that affects the overall molecular conformation.

3. Supramolecular features

In the crystal (Fig. 2), molecules are linked into screw chains by weak C11—H11A⋯O2 interactions (Fig. 2 and Table 1). Additional C5—H5A···Cg1 contacts link molecules into chains along the c-axis direction (Fig. 3 and Table 1) resulting in sheets parallel to the ac plane and stacked along the b axis (Fig. 4).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2ⁱ	0.95	2.47	3.3709 (17)	158
C14—H14A⋯O1ⁱⁱ	0.95	2.57	3.2281 (17)	126
C5—H5A⋯Cg1ⁱⁱⁱ	0.95	2.68	3.3918 (13)	132
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Screw chains of molecules of (I)

linked by C—H⋯O contacts (shown as dashed lines).

Figure 3
C—H⋯π contacts for (I)

, shown as dotted lines, with ring centroids shown as coloured spheres. Cg1 is the centroid of the C1–C6 ring.

Figure 4
The packing of (I)

, viewed along the b axis, showing the stacking of sheets of Ni^II complex molecules. Only H atoms involved in weak C—H⋯O interactions are shown for clarity.

4. Database survey

A search of the Cambridge Structural Database (Version 5.35, November 2013 with 3 updates; Allen, 2002 ) reveals a total of 1191 Ni^II complexes with an NiN₂O₂ coordination sphere. No fewer than 333 of these had the Ni^II atom chelated by two 3-(iminomethyl)phenolate residues. No corresponding structures with a benzyl or substituted benzyl unit bound to the imino N atom were found. However, extending the search to allow additional substitution on the phenolate ring resulted in seven discrete structures including the closely related bis(2-[(E)-(4-fluorobenzyl)iminomethyl]-6-methoxyphenolato-κ²N,O¹)nickel(II) (Bahron et al., 2011) and bis{2-[(benzylimino)methyl]-5-methoxyphenolato}nickel(II) (Gou et al., 2013 )

5. Synthesis and crystallization

N-4-Methoxybenzylsalicylideneimine (5 mmol, 0.6041 g) was dissolved in ethanol (15 ml). An ethanolic solution of nickel(II) acetate tetrahydrate (2.5 mmol, 0.6216 g) was added dropwise to the former solution and the mixture heated under reflux for 4 h, producing a green solid. The solid was filtered off, washed with ice-cold ethanol and air-dried at room temperature. The solid product was recrystallized from chloroform, yielding green crystals (yield 43.3%; m.p. 469–472 K). Analytical data for [Ni(C₂₈H₃₀N₂O₄)]: C 66.82, H 5.23, N 5.19%; found: C 67.03, H 5.28, N 5.15%. IR (KBr, cm⁻¹): ν(C=N) 1605 (s), ν(C—N) 1391 (s), ν(C—O) 1325 (s), ν(Ni—O) 598 (w), ν(Ni—N) 437 (w).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 for aromatic, 0.99 for CH₂ and 0.98 Å for CH₃ hydrogens. The U_iso(H) values were constrained to be 1.5U_eq of the carrier atom for methyl H atoms and 1.2U_eq for the remaining H atoms. A rotating-group model was used for the methyl groups.

Table 2
Experimental details

Crystal data
Chemical formula	[Ni(C₁₅H₁₄NO₂)₂]
M_r	539.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.1847 (2), 5.6738 (1), 17.7620 (3)
β (°)	95.682 (1)
V (Å³)	1221.92 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.84
Crystal size (mm)	0.52 × 0.30 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.670, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	14541, 3542, 3092
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.05
No. of reflections	3542
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.32
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008 ), PLATON (Spek, 2009 ), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1014286

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681401650X/sj5419sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681401650X/sj5419Isup2.hkl

checkCIF report

Chemical context top

Schiff bases have often been used as chelating ligands in coordination chemistry as they readily form stable complexes with most transition metal ions (Kalita et al., 2014; Mohamed et al., 2010). Metal complexes of Schiff bases containing nitrogen and other donor atoms have received attention because of their stability, biological activity (Islam et al., 2014) and potential applications in other fields, such as catalysis (Mohd Tajuddin et al., 2012). The title compound, bis{2-[(E)-(4-methoxylbenzyl)iminomethyl]phenolato-κ²N,O¹}nickel(II), (I), is related to bis{2-[1-(benzylimino)ethyl]phenolato}palladium(II) (Mohd Tajuddin et al., 2010) in terms of the geometry around the metal centre. However, we have extended our investigation to include a nickel compound with a Schiff base ligand that has a 4-methoxy substituent on the phenyl ring of the benzyl unit bound to the imine N atom (Fig. 1).

Structural commentary top

The asymmetric unit of (I) consists of an Ni^II cation that lies on an inversion centre and a Schiff base anion that functions as a bidentate ligand (Fig. 1). The N₂O₂ donor set of the chelating Schiff base ligands has the N1 and O1 donor atoms mutually trans, in a distorted square-planar coordination geometry, with O1—Ni1—N1 = 92.30 (4)° and O1—Ni1—N1ⁱ = 87.70 (4)°[symmetry code: (i) -x+1, -y, -z+1] and a maximum deviation from the NiO₂N₂ least-squares plane of 0.731 (1) Å for the N1 atom. The Ni1—N1 and Ni1—O1 distances in the N₂O₂ coordination plane are 1.9191 (11) and 1.8407 (9) Å, respectively. These are similar to those observed in the other closely related Ni^II complexes with N₂O₂-coordinating Schiff base ligands (Bahron et al., 2011; Mohd Tajuddin et al., 2010). Other bond lengths and angles observed in the structure are also normal. The methoxy substituent is coplanar with the ring to which it is bound, the C15—O2—C12—C13 torsion angle being 3.93 (2)°. The plane of the methoxybenzene ring (C1–C6) makes a dihedral angle of 84.92 (6)° with that of the phenolate benzene ring (C9–C14). A weak intramolecular C14—H14···O1 contact is also observed that affects the overall molecular conformation.

Supramolecular features top

In the crystal (Fig. 2), molecules are linked into screw chains by weak C11—H11A···O1 interactions (Fig. 2 and Table 1). C5—H5A···Cg1 contacts link molecules into chains along the c-axis direction (Fig. 3 and Table 1) resulting in sheets parallel to the ac plane and stacked along the b axis (Fig. 4).

Database survey top

A search of the Cambridge Structural Database (Version 5.35, November 2013 with 3 updates; Allen, 2002) reveals a total of 1191 Ni^II complexes with an NiN₂O₂ coordination sphere. No fewer than 333 of these had the Ni atom chelated by two 3-(iminomethyl)phenolate residues. No corresponding structures with a benzyl or substituted benzyl unit bound to the imino N atom were found. However, extending the search to allow additional substitution on the phenolate ring resulted in seven discrete structures including the closely related bis(2-[(E)-(4-fluorobenzyl)iminomethyl]-6-methoxyphenolato-κ²N,O¹)nickel(II) (Bahron et al., 2011) and bis{2-[(benzylimino)methyl]-5-methoxyphenolato}nickel(II) (Gou et al., 2013)

Synthesis and crystallization top

N-4-Methoxybenzylsalicylideneimine (5 mmol, 0.6041 g) was dissolved in ethanol (15 ml). An ethanolic solution of nickel(II) acetate tetrahydrate (2.5 mmol, 0.6216 g) was added dropwise to the former solution and the mixture heated under reflux for 4 h, producing a green solid. The solid was filtered off, washed with ice-cold ethanol and air-dried at room temperature. The solid product was recrystallized from chloroform, yielding green crystals (yield 43.3%; m.p. 469–472 K). Analytical data for [Ni(C₂₈H₃₀N₂O₄)]: C 66.82, H 5.23, N 5.19%; found: C 67.03, H 5.28, N 5.15%. IR (KBr, cm^-1): ν(C═N) 1605 (s), ν(C—N) 1391 (s), ν(C—O) 1325 (s), ν(Ni—O) 598 (w), ν(Ni—N) 437 (w).

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 for aromatic, 0.99 for CH₂ and 0.98 Å for CH₃ hydrogens. The U_iso(H) values were constrained to be 1.5U_eq of the carrier atom for methyl H atoms and 1.2U_eq for the remaining H atoms. A rotating-group model was used for the methyl groups.

Related literature top

For related literature, see: Bahron et al. (2011); Gou et al. (2013); Islam et al. (2014); Kalita et al. (2014); Mohamed et al. (2010); Mohd Tajuddin, Bahron, Kassim, Wan Ibrahim & Fun (2012); Mohd Tajuddin, Bahron, Wan Ibrahim & Yamin (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. The other Schiff base ligand is generated by the symmetry code (-x+1, -y, -z+1).
	Fig. 2. Screw chains of molecules of (I) linked by C—H···O contacts (shown as dashed lines).
	Fig. 3. C—H···π contacts for (I), shown as dotted lines, with ring centroids shown as coloured spheres. Cg1 is the centroid of the C1–C6 ring.
	Fig. 4. The packing of (I), viewed along the b axis, showing the stacking of sheets of Ni^II complex molecules. Only H atoms involved in weak C—H···O interactions are shown for clarity.

Bis{2-[(E)-(4-methoxylbenzyl)iminomethyl]phenolato-κ²N,O¹}nickel(II) top

Crystal data top

[Ni(C₁₅H₁₄NO₂)₂]	F(000) = 564
M_r = 539.23	D_x = 1.466 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 469–472 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.1847 (2) Å	Cell parameters from 3542 reflections
b = 5.6738 (1) Å	θ = 1.7–30.0°
c = 17.7620 (3) Å	µ = 0.84 mm⁻¹
β = 95.682 (1)°	T = 100 K
V = 1221.92 (4) Å³	Needle, green
Z = 2	0.52 × 0.30 × 0.16 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3542 independent reflections
Radiation source: sealed tube	3092 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.670, T_max = 0.876	k = −7→7
14541 measured reflections	l = −24→24

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0313P)² + 0.7976P] where P = (F_o² + 2F_c²)/3
3542 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Ni(C₁₅H₁₄NO₂)₂]	V = 1221.92 (4) Å³
M_r = 539.23	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1847 (2) Å	µ = 0.84 mm⁻¹
b = 5.6738 (1) Å	T = 100 K
c = 17.7620 (3) Å	0.52 × 0.30 × 0.16 mm
β = 95.682 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3542 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3092 reflections with I > 2σ(I)
T_min = 0.670, T_max = 0.876	R_int = 0.019
14541 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.05	Δρ_max = 0.42 e Å⁻³
3542 reflections	Δρ_min = −0.32 e Å⁻³
170 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.5000	0.0000	0.5000	0.01253 (7)
O1	0.58126 (8)	−0.03642 (16)	0.41876 (5)	0.01676 (19)
O2	−0.03916 (8)	−0.2287 (2)	0.34237 (6)	0.0272 (2)
N1	0.42000 (8)	0.2622 (2)	0.45360 (6)	0.0142 (2)
C1	0.60209 (10)	0.1191 (2)	0.36758 (6)	0.0141 (2)
C2	0.68624 (10)	0.0696 (3)	0.31981 (7)	0.0164 (2)
H2A	0.7260	−0.0744	0.3255	0.020*
C3	0.71053 (10)	0.2297 (3)	0.26525 (7)	0.0176 (2)
H3A	0.7676	0.1945	0.2343	0.021*
C4	0.65287 (11)	0.4428 (3)	0.25451 (7)	0.0182 (3)
H4A	0.6698	0.5501	0.2163	0.022*
C5	0.57101 (10)	0.4940 (2)	0.30048 (7)	0.0157 (2)
H5A	0.5315	0.6380	0.2938	0.019*
C6	0.54531 (10)	0.3354 (2)	0.35715 (6)	0.0138 (2)
C7	0.45329 (10)	0.3875 (2)	0.39913 (7)	0.0146 (2)
H7A	0.4130	0.5271	0.3857	0.018*
C8	0.31199 (10)	0.3363 (2)	0.47834 (7)	0.0163 (2)
H8A	0.2966	0.5015	0.4629	0.020*
H8B	0.3151	0.3279	0.5342	0.020*
C9	0.22048 (10)	0.1787 (2)	0.44360 (7)	0.0159 (2)
C10	0.16960 (11)	0.2254 (3)	0.37107 (7)	0.0209 (3)
H10A	0.1939	0.3559	0.3436	0.025*
C11	0.08462 (11)	0.0860 (3)	0.33834 (7)	0.0235 (3)
H11A	0.0517	0.1204	0.2888	0.028*
C12	0.04753 (10)	−0.1046 (3)	0.37812 (7)	0.0194 (3)
C13	0.09757 (11)	−0.1573 (3)	0.44988 (8)	0.0216 (3)
H13A	0.0735	−0.2887	0.4770	0.026*
C14	0.18353 (11)	−0.0150 (3)	0.48172 (8)	0.0203 (3)
H14A	0.2176	−0.0518	0.5307	0.024*
C15	−0.08444 (12)	−0.4144 (3)	0.38380 (9)	0.0274 (3)
H15A	−0.1488	−0.4812	0.3537	0.041*
H15B	−0.1069	−0.3521	0.4314	0.041*
H15C	−0.0287	−0.5376	0.3947	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01363 (11)	0.01119 (12)	0.01281 (10)	0.00205 (8)	0.00150 (7)	0.00034 (8)
O1	0.0207 (4)	0.0148 (5)	0.0153 (4)	0.0041 (4)	0.0044 (3)	0.0021 (3)
O2	0.0239 (5)	0.0353 (6)	0.0210 (5)	−0.0062 (5)	−0.0041 (4)	−0.0053 (4)
N1	0.0138 (4)	0.0131 (5)	0.0157 (4)	0.0010 (4)	0.0010 (3)	−0.0012 (4)
C1	0.0146 (5)	0.0148 (6)	0.0126 (5)	−0.0009 (5)	−0.0009 (4)	−0.0015 (4)
C2	0.0158 (5)	0.0168 (6)	0.0165 (5)	0.0003 (5)	0.0013 (4)	−0.0021 (5)
C3	0.0159 (5)	0.0198 (7)	0.0174 (5)	−0.0029 (5)	0.0025 (4)	−0.0026 (5)
C4	0.0187 (5)	0.0181 (6)	0.0179 (5)	−0.0039 (5)	0.0016 (4)	0.0015 (5)
C5	0.0156 (5)	0.0133 (6)	0.0176 (5)	−0.0021 (5)	−0.0007 (4)	0.0011 (5)
C6	0.0144 (5)	0.0134 (6)	0.0133 (5)	−0.0008 (4)	−0.0009 (4)	−0.0009 (4)
C7	0.0149 (5)	0.0123 (6)	0.0160 (5)	0.0010 (5)	−0.0012 (4)	−0.0009 (5)
C8	0.0159 (5)	0.0149 (6)	0.0183 (5)	0.0039 (5)	0.0029 (4)	−0.0004 (5)
C9	0.0140 (5)	0.0171 (6)	0.0167 (5)	0.0049 (5)	0.0026 (4)	−0.0008 (5)
C10	0.0201 (6)	0.0250 (7)	0.0178 (5)	0.0023 (5)	0.0027 (4)	0.0036 (5)
C11	0.0221 (6)	0.0340 (8)	0.0141 (5)	0.0021 (6)	0.0000 (4)	0.0007 (6)
C12	0.0163 (5)	0.0243 (7)	0.0174 (5)	0.0023 (5)	0.0006 (4)	−0.0057 (5)
C13	0.0212 (6)	0.0214 (7)	0.0216 (6)	−0.0012 (5)	−0.0007 (5)	0.0019 (5)
C14	0.0187 (6)	0.0227 (7)	0.0185 (6)	0.0009 (5)	−0.0030 (4)	0.0029 (5)
C15	0.0219 (6)	0.0282 (8)	0.0317 (7)	−0.0039 (6)	0.0007 (5)	−0.0100 (7)

Geometric parameters (Å, º) top

Ni1—O1	1.8407 (9)	C6—C7	1.4374 (16)
Ni1—O1ⁱ	1.8407 (9)	C7—H7A	0.9500
Ni1—N1	1.9191 (11)	C8—C9	1.5123 (18)
Ni1—N1ⁱ	1.9191 (11)	C8—H8A	0.9900
O1—C1	1.3095 (15)	C8—H8B	0.9900
O2—C12	1.3717 (16)	C9—C14	1.3892 (19)
O2—C15	1.427 (2)	C9—C10	1.3986 (17)
N1—C7	1.2977 (16)	C10—C11	1.384 (2)
N1—C8	1.4887 (15)	C10—H10A	0.9500
C1—C6	1.4123 (18)	C11—C12	1.392 (2)
C1—C2	1.4221 (16)	C11—H11A	0.9500
C2—C3	1.3813 (18)	C12—C13	1.3898 (18)
C2—H2A	0.9500	C13—C14	1.3967 (19)
C3—C4	1.402 (2)	C13—H13A	0.9500
C3—H3A	0.9500	C14—H14A	0.9500
C4—C5	1.3810 (17)	C15—H15A	0.9800
C4—H4A	0.9500	C15—H15B	0.9800
C5—C6	1.4080 (17)	C15—H15C	0.9800
C5—H5A	0.9500

O1—Ni1—O1ⁱ	180.000 (1)	C6—C7—H7A	116.9
O1—Ni1—N1	92.30 (4)	N1—C8—C9	110.50 (10)
O1ⁱ—Ni1—N1	87.70 (4)	N1—C8—H8A	109.5
O1—Ni1—N1ⁱ	87.70 (4)	C9—C8—H8A	109.5
O1ⁱ—Ni1—N1ⁱ	92.30 (4)	N1—C8—H8B	109.5
N1—Ni1—N1ⁱ	180.00 (6)	C9—C8—H8B	109.5
C1—O1—Ni1	128.67 (8)	H8A—C8—H8B	108.1
C12—O2—C15	117.36 (11)	C14—C9—C10	117.60 (12)
C7—N1—C8	114.59 (11)	C14—C9—C8	122.03 (11)
C7—N1—Ni1	124.19 (9)	C10—C9—C8	120.37 (12)
C8—N1—Ni1	121.22 (8)	C11—C10—C9	121.56 (13)
O1—C1—C6	123.41 (11)	C11—C10—H10A	119.2
O1—C1—C2	118.82 (12)	C9—C10—H10A	119.2
C6—C1—C2	117.77 (11)	C10—C11—C12	119.86 (12)
C3—C2—C1	120.40 (12)	C10—C11—H11A	120.1
C3—C2—H2A	119.8	C12—C11—H11A	120.1
C1—C2—H2A	119.8	O2—C12—C13	124.20 (13)
C2—C3—C4	121.55 (12)	O2—C12—C11	115.95 (12)
C2—C3—H3A	119.2	C13—C12—C11	119.84 (13)
C4—C3—H3A	119.2	C12—C13—C14	119.37 (13)
C5—C4—C3	118.84 (12)	C12—C13—H13A	120.3
C5—C4—H4A	120.6	C14—C13—H13A	120.3
C3—C4—H4A	120.6	C9—C14—C13	121.74 (12)
C4—C5—C6	120.87 (12)	C9—C14—H14A	119.1
C4—C5—H5A	119.6	C13—C14—H14A	119.1
C6—C5—H5A	119.6	O2—C15—H15A	109.5
C5—C6—C1	120.55 (11)	O2—C15—H15B	109.5
C5—C6—C7	118.67 (12)	H15A—C15—H15B	109.5
C1—C6—C7	120.51 (11)	O2—C15—H15C	109.5
N1—C7—C6	126.28 (12)	H15A—C15—H15C	109.5
N1—C7—H7A	116.9	H15B—C15—H15C	109.5

N1—Ni1—O1—C1	22.59 (11)	Ni1—N1—C7—C6	9.30 (18)
N1ⁱ—Ni1—O1—C1	−157.41 (11)	C5—C6—C7—N1	−178.90 (12)
O1—Ni1—N1—C7	−19.81 (11)	C1—C6—C7—N1	7.05 (19)
O1—Ni1—N1—C8	159.85 (9)	C7—N1—C8—C9	99.88 (13)
O1ⁱ—Ni1—N1—C8	−20.15 (9)	Ni1—N1—C8—C9	−79.80 (11)
Ni1—O1—C1—C6	−13.67 (17)	N1—C8—C9—C14	95.30 (14)
Ni1—O1—C1—C2	166.19 (9)	N1—C8—C9—C10	−84.93 (14)
O1—C1—C2—C3	−179.94 (11)	C14—C9—C10—C11	0.7 (2)
C6—C1—C2—C3	−0.06 (18)	C8—C9—C10—C11	−179.09 (12)
C1—C2—C3—C4	−0.79 (19)	C9—C10—C11—C12	0.5 (2)
C2—C3—C4—C5	0.89 (19)	C15—O2—C12—C13	3.9 (2)
C3—C4—C5—C6	−0.13 (19)	C15—O2—C12—C11	−175.51 (13)
C4—C5—C6—C1	−0.71 (18)	C10—C11—C12—O2	178.05 (12)
C4—C5—C6—C7	−174.76 (11)	C10—C11—C12—C13	−1.4 (2)
O1—C1—C6—C5	−179.33 (11)	O2—C12—C13—C14	−178.31 (13)
C2—C1—C6—C5	0.80 (17)	C11—C12—C13—C14	1.1 (2)
O1—C1—C6—C7	−5.40 (18)	C10—C9—C14—C13	−1.0 (2)
C2—C1—C6—C7	174.74 (11)	C8—C9—C14—C13	178.78 (12)
C8—N1—C7—C6	−170.38 (11)	C12—C13—C14—C9	0.1 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2ⁱⁱ	0.95	2.47	3.3709 (17)	158
C14—H14A···O1ⁱ	0.95	2.57	3.2281 (17)	126
C5—H5A···Cg1ⁱⁱⁱ	0.95	2.68	3.3918 (13)	132

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2ⁱ	0.95	2.47	3.3709 (17)	158
C14—H14A···O1ⁱⁱ	0.95	2.57	3.2281 (17)	126
C5—H5A···Cg1ⁱⁱⁱ	0.95	2.68	3.3918 (13)	132

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₅H₁₄NO₂)₂]
M_r	539.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.1847 (2), 5.6738 (1), 17.7620 (3)
β (°)	95.682 (1)
V (Å³)	1221.92 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.52 × 0.30 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.670, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	14541, 3542, 3092
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.05
No. of reflections	3542
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.32

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

The authors would like to acknowledge the Ministry of Education of Malaysia for research grants Nos. 600-RMI/FRGS 5/3 (51/2013) and (52/2013), Universiti Teknologi MARA for research grant No. 600-RMI/DANA 5/3/CG (15/2012), and Universiti Sains Malaysia for the use of the X-ray diffraction facilities.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bahron, H., Tajuddin, A. M., Ibrahim, W. N. W., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, m1010–m1011. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gou, Y., Liu, Y., Zhao, X. H., Li, Y. G. & Chen, W. (2013). Koord. Khim. 39, 134–140. Web of Science CrossRef CAS Google Scholar
Islam, M. A. A. A., Sheikh, M. C., Alam, M. S., Zangrando, E., Alam, M. A., Tarafder, M. T. H. & Miyatake, R. (2014). Transition Met. Chem. 39, 141–149. Web of Science CSD CrossRef CAS Google Scholar
Kalita, M., Gogoi, P., Barman, P., Sarma, B., Buragohain, A. K. & Kalita, R. D. (2014). Polyhedron, 74, 93–98. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mohamed, G. G., Zayed, M. A. & Abdallah, S. M. (2010). J. Mol. Struct. 979, 62–71. Web of Science CrossRef CAS Google Scholar
Mohd Tajuddin, A., Bahron, H., Kassim, K., Wan Ibrahim, W. N. & Fun, H.-K. (2012). Adv. Mater. Res. 554–556, 736–740. CrossRef Google Scholar
Mohd Tajuddin, A., Bahron, H., Wan Ibrahim, W. N. & Yamin, B. M. (2010). Acta Cryst. E66, m1100. 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 8| August 2014| Pages 104-106

doi:10.1107/S160053681401650X

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