{1,1′-[2,2-Dimethyl­propane-1,3-diylbis(nitrilo­methyl­idyne)]di-2-naphtholato}nickel(II)

Kargar, H.; Kia, R.; Khan, I.U.; Zare, K.

doi:10.1107/S1600536810007373

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m360

doi:10.1107/S1600536810007373

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{1,1′-[2,2-Dimethylpropane-1,3-diylbis(nitrilomethylidyne)]di-2-naphtholato}nickel(II)

Hadi Kargar,^a Reza Kia,^b ‡ Islam Ullah Khan ^c ^* and Karim Zare ^b

^aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, ^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^cMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan
^*Correspondence e-mail: iuklodhi@yahoo.com

(Received 20 February 2010; accepted 26 February 2010; online 3 March 2010)

In the title Schiff base complex, [Ni(C₂₇H₂₄N₂O₂)], the Ni^II atom shows a slightly distorted square-planar geometry. The dihedral angle between the mean planes of the two aromatic rings is 6.16 (6)°. In the crystal, pairs of intermolecular weak C—H⋯O hydrogen bonds link neighboring molecules into a chain along the a axis. The crystal structure is further stabilized by two intermolecular π–π interactions with centroid–centroid distances of 3.7252 (13) and 3.8323 (13) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to Schiff base–metal complexes, see: Granovski et al. (1993 ); Blower et al. (1998 ); Elmali et al. (2000 ).

Experimental

Crystal data

[Ni(C₂₇H₂₄N₂O₂)]
M_r = 467.19
Triclinic, $[P \overline 1]$
a = 7.5016 (2) Å
b = 11.3583 (3) Å
c = 13.0173 (3) Å
α = 87.846 (2)°
β = 89.496 (1)°
γ = 76.196 (1)°
V = 1076.35 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 296 K
0.45 × 0.23 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.680, T_max = 0.897
23454 measured reflections
5293 independent reflections
3802 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.085
S = 1.02
5293 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O2	1.8453 (12)
Ni1—O1	1.8501 (12)
Ni1—N1	1.8617 (14)
Ni1—N2	1.8632 (14)

O2—Ni1—O1	84.48 (5)
O1—Ni1—N1	92.08 (6)
O2—Ni1—N2	92.02 (6)
N1—Ni1—N2	91.51 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯O1ⁱ	0.97	2.46	3.422 (2)	171
C14—H14B⋯O2ⁱⁱ	0.97	2.54	3.502 (2)	170
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x, -y+2, -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/S1600536810007373/bq2198sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007373/bq2198Isup2.hkl

checkCIF report

Comment top

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with the 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 structural research (Elmali et al., 2000; Blower et al., 1998). 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. The geometry around the Ni(II) atom is a slightly distorted square-planar which is coordinated by the N₂O₂ donor atoms of the desired potentially tetradenate Schiff base ligand (Table 1). Pairs of weak intermolecular C—H···O hydrogen bonds (Table 2) link neighboring molecules into a chain along the a-axis. The dihedral angle between the mean planes of the two aromatic rings is 6.16 (6)°. The crystal structure is further stabilized by the intermolecular π–π interactions [Cg1···Cg2ⁱ = 3.7252 (13) and Cg1···Cg2ⁱⁱ = 3.8323 (13) Å; Cg1 and Cg2 are the centroids of the C4/C5/C6/C7/C8/C9 and C17/C18/C19/C20/C21/C22 benzene rings].

Related literature top

For bond-length data, see: Allen et al. (1987). For background to Schiff base–metal complexes, see: Granovski et al. (1993); Blower et al. (1998); Elmali et al. (2000).

Experimental top

The title compound was synthesized by adding bis(naphthaldiminato)-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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The 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 h-bonds are shown as dashed lines.

{1,1'-[2,2-Dimethylpropane-1,3-diylbis(nitrilomethylidyne)]di-2- naphtholato}nickel(II) top

Crystal data top

[Ni(C₂₇H₂₄N₂O₂)]	Z = 2
M_r = 467.19	F(000) = 488
Triclinic, P1	D_x = 1.442 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5016 (2) Å	Cell parameters from 7107 reflections
b = 11.3583 (3) Å	θ = 2.4–28.2°
c = 13.0173 (3) Å	µ = 0.93 mm⁻¹
α = 87.846 (2)°	T = 296 K
β = 89.496 (1)°	Block, red
γ = 76.196 (1)°	0.45 × 0.23 × 0.12 mm
V = 1076.35 (5) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5293 independent reflections
Radiation source: fine-focus sealed tube	3802 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→10
T_min = 0.680, T_max = 0.897	k = −15→15
23454 measured reflections	l = −17→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0358P)² + 0.2515P] where P = (F_o² + 2F_c²)/3
5293 reflections	(Δ/σ)_max = 0.002
289 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Ni(C₂₇H₂₄N₂O₂)]	γ = 76.196 (1)°
M_r = 467.19	V = 1076.35 (5) Å³
Triclinic, P1	Z = 2
a = 7.5016 (2) Å	Mo Kα radiation
b = 11.3583 (3) Å	µ = 0.93 mm⁻¹
c = 13.0173 (3) Å	T = 296 K
α = 87.846 (2)°	0.45 × 0.23 × 0.12 mm
β = 89.496 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5293 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3802 reflections with I > 2σ(I)
T_min = 0.680, T_max = 0.897	R_int = 0.034
23454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
5293 reflections	Δρ_min = −0.28 e Å⁻³
289 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	0.25048 (3)	1.00150 (2)	−0.002820 (16)	0.03427 (8)
O1	0.22183 (18)	1.16579 (11)	0.01506 (9)	0.0429 (3)
O2	0.20302 (18)	1.04717 (11)	−0.13928 (9)	0.0417 (3)
N1	0.30698 (19)	0.96456 (13)	0.13543 (11)	0.0351 (3)
N2	0.26661 (19)	0.83899 (13)	−0.02841 (10)	0.0337 (3)
C1	0.1646 (2)	1.22188 (16)	0.09929 (14)	0.0376 (4)
C2	0.1041 (3)	1.35083 (18)	0.09098 (15)	0.0473 (5)
H2A	0.1129	1.3909	0.0282	0.057*
C3	0.0340 (3)	1.41573 (19)	0.17329 (17)	0.0528 (5)
H3A	−0.0049	1.4997	0.1655	0.063*
C4	0.0180 (3)	1.35973 (19)	0.27082 (15)	0.0468 (5)
C5	−0.0599 (3)	1.4277 (2)	0.35586 (19)	0.0611 (6)
H5A	−0.1016	1.5114	0.3481	0.073*
C6	−0.0747 (3)	1.3721 (3)	0.44875 (19)	0.0672 (7)
H6A	−0.1248	1.4179	0.5043	0.081*
C7	−0.0150 (3)	1.2469 (3)	0.46062 (16)	0.0607 (6)
H7A	−0.0265	1.2091	0.5241	0.073*
C8	0.0610 (3)	1.1785 (2)	0.37951 (15)	0.0503 (5)
H8A	0.0988	1.0947	0.3887	0.060*
C9	0.0826 (2)	1.23247 (18)	0.28295 (14)	0.0410 (4)
C10	0.1613 (2)	1.16358 (17)	0.19568 (13)	0.0365 (4)
C11	0.2568 (2)	1.03958 (17)	0.20838 (13)	0.0373 (4)
H11A	0.2857	1.0099	0.2752	0.045*
C12	0.4315 (2)	0.84660 (16)	0.15985 (14)	0.0395 (4)
H12A	0.4724	0.8452	0.2305	0.047*
H12B	0.5387	0.8369	0.1159	0.047*
C13	0.3433 (3)	0.73967 (16)	0.14614 (14)	0.0402 (4)
C14	0.2095 (3)	0.76569 (17)	0.05547 (13)	0.0405 (4)
H14A	0.1980	0.6893	0.0288	0.049*
H14B	0.0896	0.8079	0.0798	0.049*
C15	0.3060 (2)	0.79094 (16)	−0.11691 (13)	0.0357 (4)
H15A	0.3179	0.7077	−0.1198	0.043*
C16	0.3326 (2)	0.85414 (16)	−0.21032 (13)	0.0334 (4)
C17	0.4069 (2)	0.78886 (16)	−0.30034 (13)	0.0349 (4)
C18	0.4910 (3)	0.66487 (18)	−0.29783 (15)	0.0467 (5)
H18A	0.5003	0.6210	−0.2355	0.056*
C19	0.5602 (3)	0.6063 (2)	−0.38503 (17)	0.0543 (5)
H19A	0.6147	0.5236	−0.3810	0.065*
C20	0.5499 (3)	0.6689 (2)	−0.47890 (16)	0.0553 (6)
H20A	0.5966	0.6284	−0.5377	0.066*
C21	0.4713 (3)	0.7895 (2)	−0.48451 (15)	0.0490 (5)
H21A	0.4645	0.8314	−0.5477	0.059*
C22	0.3996 (2)	0.85265 (17)	−0.39621 (13)	0.0385 (4)
C23	0.3185 (3)	0.97905 (18)	−0.40085 (14)	0.0437 (4)
H23A	0.3093	1.0209	−0.4641	0.052*
C24	0.2541 (3)	1.04042 (17)	−0.31591 (13)	0.0418 (4)
H24A	0.2027	1.1234	−0.3219	0.050*
C25	0.2638 (2)	0.98001 (16)	−0.21745 (13)	0.0345 (4)
C26	0.2337 (3)	0.7194 (2)	0.24235 (16)	0.0643 (6)
H26A	0.1385	0.7910	0.2535	0.096*
H26B	0.3141	0.7027	0.3008	0.096*
H26C	0.1798	0.6519	0.2330	0.096*
C27	0.4978 (3)	0.6277 (2)	0.1266 (2)	0.0680 (7)
H27A	0.5647	0.6425	0.0662	0.102*
H27B	0.4465	0.5592	0.1168	0.102*
H27C	0.5793	0.6113	0.1846	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.04204 (14)	0.03339 (13)	0.02735 (13)	−0.00840 (9)	0.00091 (9)	−0.00494 (9)
O1	0.0599 (8)	0.0363 (7)	0.0329 (7)	−0.0114 (6)	0.0073 (6)	−0.0074 (5)
O2	0.0568 (8)	0.0342 (7)	0.0299 (6)	−0.0021 (6)	0.0002 (6)	−0.0039 (5)
N1	0.0380 (8)	0.0368 (8)	0.0313 (8)	−0.0099 (7)	0.0004 (6)	−0.0037 (6)
N2	0.0391 (8)	0.0354 (8)	0.0276 (7)	−0.0105 (6)	−0.0005 (6)	−0.0014 (6)
C1	0.0387 (9)	0.0386 (10)	0.0374 (10)	−0.0116 (8)	0.0002 (7)	−0.0094 (8)
C2	0.0562 (12)	0.0402 (11)	0.0469 (11)	−0.0134 (9)	0.0001 (9)	−0.0071 (9)
C3	0.0546 (12)	0.0410 (11)	0.0629 (14)	−0.0090 (10)	−0.0027 (10)	−0.0165 (10)
C4	0.0404 (10)	0.0527 (12)	0.0483 (12)	−0.0096 (9)	0.0003 (8)	−0.0236 (10)
C5	0.0497 (12)	0.0629 (15)	0.0685 (16)	−0.0042 (11)	0.0026 (11)	−0.0362 (13)
C6	0.0504 (13)	0.096 (2)	0.0538 (15)	−0.0083 (13)	0.0074 (10)	−0.0419 (14)
C7	0.0506 (12)	0.091 (2)	0.0405 (12)	−0.0154 (13)	0.0052 (9)	−0.0209 (12)
C8	0.0456 (11)	0.0685 (14)	0.0376 (11)	−0.0138 (10)	0.0017 (8)	−0.0140 (10)
C9	0.0319 (9)	0.0539 (12)	0.0391 (10)	−0.0115 (8)	−0.0010 (7)	−0.0177 (9)
C10	0.0355 (9)	0.0435 (10)	0.0329 (9)	−0.0125 (8)	0.0004 (7)	−0.0113 (8)
C11	0.0387 (9)	0.0454 (11)	0.0294 (9)	−0.0125 (8)	−0.0002 (7)	−0.0048 (8)
C12	0.0404 (10)	0.0402 (10)	0.0363 (10)	−0.0063 (8)	−0.0045 (8)	−0.0014 (8)
C13	0.0485 (11)	0.0368 (10)	0.0352 (10)	−0.0102 (9)	−0.0012 (8)	0.0023 (8)
C14	0.0496 (11)	0.0424 (10)	0.0336 (10)	−0.0193 (9)	0.0020 (8)	−0.0008 (8)
C15	0.0395 (9)	0.0326 (9)	0.0360 (10)	−0.0098 (8)	−0.0021 (7)	−0.0038 (8)
C16	0.0348 (9)	0.0371 (10)	0.0294 (9)	−0.0100 (8)	−0.0010 (7)	−0.0043 (7)
C17	0.0334 (9)	0.0414 (10)	0.0317 (9)	−0.0118 (8)	−0.0014 (7)	−0.0060 (8)
C18	0.0531 (12)	0.0439 (11)	0.0412 (11)	−0.0070 (9)	0.0023 (9)	−0.0063 (9)
C19	0.0575 (13)	0.0458 (12)	0.0558 (14)	−0.0030 (10)	0.0071 (10)	−0.0158 (10)
C20	0.0583 (13)	0.0654 (15)	0.0435 (12)	−0.0148 (11)	0.0142 (10)	−0.0235 (11)
C21	0.0558 (12)	0.0631 (14)	0.0321 (10)	−0.0212 (11)	0.0073 (9)	−0.0093 (9)
C22	0.0397 (10)	0.0471 (11)	0.0313 (9)	−0.0148 (8)	0.0004 (7)	−0.0075 (8)
C23	0.0534 (11)	0.0492 (12)	0.0297 (9)	−0.0150 (9)	−0.0035 (8)	0.0023 (8)
C24	0.0522 (11)	0.0379 (10)	0.0343 (10)	−0.0087 (9)	−0.0045 (8)	−0.0003 (8)
C25	0.0372 (9)	0.0373 (10)	0.0297 (9)	−0.0093 (8)	−0.0022 (7)	−0.0054 (7)
C26	0.0814 (16)	0.0800 (17)	0.0403 (12)	−0.0387 (14)	0.0001 (11)	0.0106 (11)
C27	0.0766 (16)	0.0431 (13)	0.0787 (17)	−0.0029 (12)	−0.0123 (13)	−0.0017 (11)

Geometric parameters (Å, º) top

Ni1—O2	1.8453 (12)	C12—H12B	0.9700
Ni1—O1	1.8501 (12)	C13—C27	1.530 (3)
Ni1—N1	1.8617 (14)	C13—C14	1.530 (2)
Ni1—N2	1.8632 (14)	C13—C26	1.532 (3)
O1—C1	1.306 (2)	C14—H14A	0.9700
O2—C25	1.308 (2)	C14—H14B	0.9700
N1—C11	1.293 (2)	C15—C16	1.426 (2)
N1—C12	1.464 (2)	C15—H15A	0.9300
N2—C15	1.295 (2)	C16—C25	1.399 (2)
N2—C14	1.470 (2)	C16—C17	1.446 (2)
C1—C10	1.399 (3)	C17—C18	1.398 (3)
C1—C2	1.426 (3)	C17—C22	1.414 (2)
C2—C3	1.354 (3)	C18—C19	1.372 (3)
C2—H2A	0.9300	C18—H18A	0.9300
C3—C4	1.416 (3)	C19—C20	1.384 (3)
C3—H3A	0.9300	C19—H19A	0.9300
C4—C9	1.414 (3)	C20—C21	1.356 (3)
C4—C5	1.414 (3)	C20—H20A	0.9300
C5—C6	1.359 (3)	C21—C22	1.411 (2)
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.388 (3)	C22—C23	1.419 (3)
C6—H6A	0.9300	C23—C24	1.353 (2)
C7—C8	1.372 (3)	C23—H23A	0.9300
C7—H7A	0.9300	C24—C25	1.425 (2)
C8—C9	1.403 (3)	C24—H24A	0.9300
C8—H8A	0.9300	C26—H26A	0.9600
C9—C10	1.444 (2)	C26—H26B	0.9600
C10—C11	1.424 (3)	C26—H26C	0.9600
C11—H11A	0.9300	C27—H27A	0.9600
C12—C13	1.532 (2)	C27—H27B	0.9600
C12—H12A	0.9700	C27—H27C	0.9600

O2—Ni1—O1	84.48 (5)	C14—C13—C12	110.48 (14)
O2—Ni1—N1	175.84 (6)	C27—C13—C26	110.90 (18)
O1—Ni1—N1	92.08 (6)	C14—C13—C26	107.42 (16)
O2—Ni1—N2	92.02 (6)	C12—C13—C26	110.25 (16)
O1—Ni1—N2	175.83 (6)	N2—C14—C13	113.35 (14)
N1—Ni1—N2	91.51 (6)	N2—C14—H14A	108.9
C1—O1—Ni1	125.17 (12)	C13—C14—H14A	108.9
C25—O2—Ni1	125.40 (11)	N2—C14—H14B	108.9
C11—N1—C12	118.80 (15)	C13—C14—H14B	108.9
C11—N1—Ni1	124.30 (13)	H14A—C14—H14B	107.7
C12—N1—Ni1	116.62 (11)	N2—C15—C16	125.85 (16)
C15—N2—C14	118.61 (15)	N2—C15—H15A	117.1
C15—N2—Ni1	124.48 (12)	C16—C15—H15A	117.1
C14—N2—Ni1	116.51 (11)	C25—C16—C15	118.56 (15)
O1—C1—C10	124.15 (17)	C25—C16—C17	120.04 (16)
O1—C1—C2	116.95 (17)	C15—C16—C17	120.90 (16)
C10—C1—C2	118.90 (17)	C18—C17—C22	117.34 (16)
C3—C2—C1	120.88 (19)	C18—C17—C16	123.42 (16)
C3—C2—H2A	119.6	C22—C17—C16	119.22 (16)
C1—C2—H2A	119.6	C19—C18—C17	121.63 (19)
C2—C3—C4	122.0 (2)	C19—C18—H18A	119.2
C2—C3—H3A	119.0	C17—C18—H18A	119.2
C4—C3—H3A	119.0	C18—C19—C20	120.7 (2)
C9—C4—C5	119.5 (2)	C18—C19—H19A	119.6
C9—C4—C3	118.73 (17)	C20—C19—H19A	119.6
C5—C4—C3	121.8 (2)	C21—C20—C19	119.53 (19)
C6—C5—C4	120.9 (2)	C21—C20—H20A	120.2
C6—C5—H5A	119.6	C19—C20—H20A	120.2
C4—C5—H5A	119.6	C20—C21—C22	121.19 (19)
C5—C6—C7	119.9 (2)	C20—C21—H21A	119.4
C5—C6—H6A	120.0	C22—C21—H21A	119.4
C7—C6—H6A	120.0	C21—C22—C17	119.57 (18)
C8—C7—C6	120.6 (2)	C21—C22—C23	121.76 (18)
C8—C7—H7A	119.7	C17—C22—C23	118.68 (16)
C6—C7—H7A	119.7	C24—C23—C22	121.89 (17)
C7—C8—C9	121.3 (2)	C24—C23—H23A	119.1
C7—C8—H8A	119.3	C22—C23—H23A	119.1
C9—C8—H8A	119.3	C23—C24—C25	121.08 (18)
C8—C9—C4	117.77 (18)	C23—C24—H24A	119.5
C8—C9—C10	122.98 (19)	C25—C24—H24A	119.5
C4—C9—C10	119.22 (18)	O2—C25—C16	124.25 (16)
C1—C10—C11	118.64 (16)	O2—C25—C24	116.85 (16)
C1—C10—C9	120.05 (18)	C16—C25—C24	118.88 (16)
C11—C10—C9	120.84 (17)	C13—C26—H26A	109.5
N1—C11—C10	125.94 (17)	C13—C26—H26B	109.5
N1—C11—H11A	117.0	H26A—C26—H26B	109.5
C10—C11—H11A	117.0	C13—C26—H26C	109.5
N1—C12—C13	113.23 (14)	H26A—C26—H26C	109.5
N1—C12—H12A	108.9	H26B—C26—H26C	109.5
C13—C12—H12A	108.9	C13—C27—H27A	109.5
N1—C12—H12B	108.9	C13—C27—H27B	109.5
C13—C12—H12B	108.9	H27A—C27—H27B	109.5
H12A—C12—H12B	107.7	C13—C27—H27C	109.5
C27—C13—C14	110.24 (16)	H27A—C27—H27C	109.5
C27—C13—C12	107.57 (17)	H27B—C27—H27C	109.5

O2—Ni1—O1—C1	151.46 (15)	C9—C10—C11—N1	168.37 (17)
N1—Ni1—O1—C1	−30.88 (15)	C11—N1—C12—C13	114.41 (18)
O1—Ni1—O2—C25	151.58 (14)	Ni1—N1—C12—C13	−71.51 (17)
N2—Ni1—O2—C25	−30.68 (14)	N1—C12—C13—C27	155.32 (16)
O1—Ni1—N1—C11	24.19 (15)	N1—C12—C13—C14	35.0 (2)
N2—Ni1—N1—C11	−153.69 (15)	N1—C12—C13—C26	−83.63 (19)
O1—Ni1—N1—C12	−149.53 (12)	C15—N2—C14—C13	115.85 (17)
N2—Ni1—N1—C12	32.58 (12)	Ni1—N2—C14—C13	−71.04 (18)
O2—Ni1—N2—C15	23.74 (14)	C27—C13—C14—N2	−85.4 (2)
N1—Ni1—N2—C15	−154.06 (14)	C12—C13—C14—N2	33.4 (2)
O2—Ni1—N2—C14	−148.93 (12)	C26—C13—C14—N2	153.68 (16)
N1—Ni1—N2—C14	33.28 (12)	C14—N2—C15—C16	168.55 (16)
Ni1—O1—C1—C10	17.2 (2)	Ni1—N2—C15—C16	−4.0 (2)
Ni1—O1—C1—C2	−163.52 (13)	N2—C15—C16—C25	−18.9 (3)
O1—C1—C2—C3	176.67 (17)	N2—C15—C16—C17	169.17 (16)
C10—C1—C2—C3	−4.0 (3)	C25—C16—C17—C18	174.81 (17)
C1—C2—C3—C4	0.3 (3)	C15—C16—C17—C18	−13.4 (3)
C2—C3—C4—C9	2.0 (3)	C25—C16—C17—C22	−3.5 (2)
C2—C3—C4—C5	−178.28 (19)	C15—C16—C17—C22	168.25 (16)
C9—C4—C5—C6	−0.5 (3)	C22—C17—C18—C19	−1.5 (3)
C3—C4—C5—C6	179.7 (2)	C16—C17—C18—C19	−179.85 (18)
C4—C5—C6—C7	−0.8 (3)	C17—C18—C19—C20	0.4 (3)
C5—C6—C7—C8	0.7 (3)	C18—C19—C20—C21	0.3 (3)
C6—C7—C8—C9	0.8 (3)	C19—C20—C21—C22	0.0 (3)
C7—C8—C9—C4	−2.0 (3)	C20—C21—C22—C17	−1.1 (3)
C7—C8—C9—C10	−179.83 (18)	C20—C21—C22—C23	179.44 (19)
C5—C4—C9—C8	1.9 (3)	C18—C17—C22—C21	1.8 (2)
C3—C4—C9—C8	−178.36 (18)	C16—C17—C22—C21	−179.80 (16)
C5—C4—C9—C10	179.77 (17)	C18—C17—C22—C23	−178.73 (17)
C3—C4—C9—C10	−0.5 (3)	C16—C17—C22—C23	−0.3 (2)
O1—C1—C10—C11	12.5 (3)	C21—C22—C23—C24	−178.18 (18)
C2—C1—C10—C11	−166.77 (16)	C17—C22—C23—C24	2.3 (3)
O1—C1—C10—C9	−175.30 (16)	C22—C23—C24—C25	−0.5 (3)
C2—C1—C10—C9	5.5 (2)	Ni1—O2—C25—C16	17.6 (2)
C8—C9—C10—C1	174.51 (17)	Ni1—O2—C25—C24	−163.95 (12)
C4—C9—C10—C1	−3.3 (2)	C15—C16—C25—O2	11.7 (3)
C8—C9—C10—C11	−13.4 (3)	C17—C16—C25—O2	−176.29 (15)
C4—C9—C10—C11	168.79 (16)	C15—C16—C25—C24	−166.67 (16)
C12—N1—C11—C10	169.46 (16)	C17—C16—C25—C24	5.3 (2)
Ni1—N1—C11—C10	−4.1 (2)	C23—C24—C25—O2	178.13 (17)
C1—C10—C11—N1	−19.5 (3)	C23—C24—C25—C16	−3.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O1ⁱ	0.97	2.46	3.422 (2)	171
C14—H14B···O2ⁱⁱ	0.97	2.54	3.502 (2)	170

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

Experimental details

Crystal data
Chemical formula	[Ni(C₂₇H₂₄N₂O₂)]
M_r	467.19
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5016 (2), 11.3583 (3), 13.0173 (3)
α, β, γ (°)	87.846 (2), 89.496 (1), 76.196 (1)
V (Å³)	1076.35 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.45 × 0.23 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.680, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	23454, 5293, 3802
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.085, 1.02
No. of reflections	5293
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.28

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

Selected geometric parameters (Å, º) top

Ni1—O2	1.8453 (12)	Ni1—N1	1.8617 (14)
Ni1—O1	1.8501 (12)	Ni1—N2	1.8632 (14)

O2—Ni1—O1	84.48 (5)	O2—Ni1—N2	92.02 (6)
O1—Ni1—N1	92.08 (6)	N1—Ni1—N2	91.51 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O1ⁱ	0.9700	2.4600	3.422 (2)	171.00
C14—H14B···O2ⁱⁱ	0.9700	2.5400	3.502 (2)	170.00

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

Footnotes

‡Thomson Reuters Researcher ID: A-5471-2009. Additional corresponding author, e-mail: zsrkk@yahoo.com.

Acknowledgements

HK and RK thank PNU for financial support and RK also thanks Islamic Azad University. IUK thanks GC University of Lahore, Pakistan, for the research facilities.

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
Elmali, A., Elerman, Y. & Svoboda, I. (2000). Acta Cryst. C56, 423–424. CSD CrossRef CAS IUCr Journals Google Scholar
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. 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 66| Part 4| April 2010| Page m360

doi:10.1107/S1600536810007373

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

{1,1′-[2,2-Di­methyl­propane-1,3-diylbis(nitrilo­methyl­­idyne)]di-2-naphtholato}nickel(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

metal-organic compounds

{1,1′-[2,2-Dimethylpropane-1,3-diylbis(nitrilomethylidyne)]di-2-naphtholato}nickel(II)