{2,2′-[1,1′-(Ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphtholato}nickel(II)

Dong, W.-K.; Wu, J.-C.; Yao, J.; Gong, S.-S.; Tong, J.-F.

doi:10.1107/S1600536809023149

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m803

doi:10.1107/S1600536809023149

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{2,2′-[1,1′-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphtholato}nickel(II)

Wen-Kui Dong,^a ^* Jian-Chao Wu,^a Jian Yao,^a Shang-Sheng Gong ^a and Jun-Feng Tong ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 11 June 2009; accepted 16 June 2009; online 20 June 2009)

In the title complex, [Ni(C₂₆H₂₂N₂O₄)], the Ni^II atom has a slight distortion toward tetrahedral geometry from a square-planar structure, coordinated by two O and two N atoms of the tetradentate salen-type bisoxime 2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]di-1-naphtholate (L²⁻) unit, with a mean deviation of 0.022 Å from the N₂O₂ plane. The N- and O-donor atoms are mutually cis. The dihedral angle between two naphthalene systems of the L²⁻ ligand is 67.59 (4)°. The crystal structure is stabilized by intermolecular C—H⋯O and C—H⋯π interactions, which link neighbouring molecules into extended chains along the b axis.

Related literature

For multidentate salen-type compounds in coordination chemistry, see: Akine et al. (2005 ); Dong et al. (2009a ,b ); Katsuki (1995 ); Ray et al. (2003 ); Sun et al. (2008 ). For the isostructural Cu complex, see: Dong et al. (2009c ).

Experimental

Crystal data

[Ni(C₂₆H₂₂N₂O₄)]
M_r = 485.17
Monoclinic, P 2₁ /n
a = 13.6975 (13) Å
b = 8.2711 (10) Å
c = 19.049 (2) Å
β = 95.346 (1)°
V = 2148.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 298 K
0.43 × 0.16 × 0.06 mm

Data collection

Siemens SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.688, T_max = 0.946
10414 measured reflections
3782 independent reflections
2179 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.126
S = 1.02
3782 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O3ⁱ	0.96	2.45	3.152 (6)	130
C3—H3C⋯Cg1ⁱⁱ	0.97	3.17	4.127 (3)	172
C15—H15A⋯Cg2ⁱⁱⁱ	0.96	3.53	4.398 (3)	152
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) x+1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023149/hg2525sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023149/hg2525Isup2.hkl

checkCIF report

Comment top

Multidentate salen-type compounds play an important role in the development of modern coordination chemistry as they readily form stable complexes with most of the transition metals, in which some could exhibit interesting properties (Katsuki, et al., 1995; Akine, et al., 2005; Ray, et al., 2003). Here, we report a new Ni^II complex based on the tetradentate salen-type bisoxime ligand 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol (Dong, et al., 2009a; Dong, et al., 2009b).

In this paper, a new mononuclear nickel(II) complex with salen-type bisoxime chelating ligand, 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol, has been synthesized (Sun, et al., 2008). The dihedral angle between the coordination plane of O3—Ni1—N1 and that of O4—Ni1—N2 is 67.59 (4)°, indicating slight distortion toward tetrahedral geometry from the square planar structure, with a mean deviation of 0.022 Å from the N₂O₂ plane. The crystal structure is further stabilized by intermolecular C15—H15A···O3 hydrogen bond and C3—H3C···π(benzene), C15—H15A···π(naphthalene) interactions (Table 1), which link neighbouring molecules into extended chains along the b axis.

Related literature top

For multidentate salen-type compounds in coordination chemistry, see: Akine et al. (2005); Dong et al. (2009a,b); Katsuki (1995); Ray et al. (2003); Sun et al. (2008). For the isostructural Cu complex, see: Dong et al. (2009c).

Experimental top

A solution of nickel(II) chloride tetrahydrate (2.8 mg, 0.0138 mmol) in methanol (3 ml) was added dropwise to a solution of 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol (4.5 mg, 0.0105 mmol) and 99% triethylamine (0.025 ml) in dichloromethane (3 ml). The color of the mixing solution turns to dark-yellow, immediately, and was allowed to stand at room temperature for about three weeks, the solvent was partially evaporated and obtained brown needle-like single crystals suitable for X-ray crystallographic analysis.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecule structure of the title complex. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Part of the supramolecular structure of the title complex Showing the formation of C15—H15A···O3 hydrogen bond and C3—H3C···π(benzene), C15—H15A···π(naphthalene) interactions.

{2,2'-[1,1'-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphtholato}nickel(II) top

Crystal data top

[Ni(C₂₆H₂₂N₂O₄)]	F(000) = 1008
M_r = 485.17	D_x = 1.500 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1885 reflections
a = 13.6975 (13) Å	θ = 2.9–22.6°
b = 8.2711 (10) Å	µ = 0.94 mm⁻¹
c = 19.049 (2) Å	T = 298 K
β = 95.346 (1)°	Prismatic, brown
V = 2148.7 (4) Å³	0.43 × 0.16 × 0.06 mm
Z = 4

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3782 independent reflections
Radiation source: fine-focus sealed tube	2179 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
T_min = 0.688, T_max = 0.946	k = −9→9
10414 measured reflections	l = −22→21

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0457P)² + 0.4257P] where P = (F_o² + 2F_c²)/3
3782 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Ni(C₂₆H₂₂N₂O₄)]	V = 2148.7 (4) Å³
M_r = 485.17	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.6975 (13) Å	µ = 0.94 mm⁻¹
b = 8.2711 (10) Å	T = 298 K
c = 19.049 (2) Å	0.43 × 0.16 × 0.06 mm
β = 95.346 (1)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3782 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2179 reflections with I > 2σ(I)
T_min = 0.688, T_max = 0.946	R_int = 0.073
10414 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.02	Δρ_max = 0.45 e Å⁻³
3782 reflections	Δρ_min = −0.38 e Å⁻³
298 parameters

Special details top

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	0.75831 (4)	0.20469 (8)	0.22591 (3)	0.0404 (2)
N1	0.7696 (2)	0.2159 (5)	0.12766 (18)	0.0427 (9)
N2	0.6275 (2)	0.2675 (4)	0.22573 (18)	0.0414 (9)
O1	0.7023 (2)	0.1391 (4)	0.07716 (16)	0.0612 (10)
O2	0.5751 (2)	0.2984 (4)	0.15860 (15)	0.0476 (8)
O3	0.89260 (19)	0.1753 (4)	0.23858 (14)	0.0468 (8)
O4	0.7640 (2)	0.1617 (4)	0.31931 (15)	0.0513 (9)
C1	0.6314 (4)	0.0466 (6)	0.1102 (3)	0.0589 (14)
H1A	0.6614	0.0022	0.1542	0.071*
H1B	0.6093	−0.0428	0.0798	0.071*
C2	0.5455 (3)	0.1494 (6)	0.1245 (3)	0.0548 (14)
H2A	0.5070	0.1728	0.0804	0.066*
H2B	0.5042	0.0898	0.1542	0.066*
C3	0.8419 (3)	0.2790 (6)	0.0185 (2)	0.0577 (14)
H3A	0.8183	0.1769	−0.0002	0.087*
H3B	0.9075	0.2965	0.0061	0.087*
H3C	0.8001	0.3640	−0.0010	0.087*
C4	0.8418 (3)	0.2780 (6)	0.0975 (2)	0.0422 (12)
C5	0.9487 (3)	0.2779 (5)	0.2089 (2)	0.0390 (11)
C6	0.9264 (3)	0.3411 (5)	0.1412 (2)	0.0408 (12)
C7	0.9930 (4)	0.4501 (6)	0.1145 (2)	0.0511 (13)
H7	0.9782	0.4920	0.0695	0.061*
C8	1.0781 (4)	0.4966 (6)	0.1518 (3)	0.0561 (14)
H8	1.1192	0.5704	0.1325	0.067*
C9	1.1038 (3)	0.4326 (6)	0.2199 (3)	0.0484 (12)
C10	1.0395 (3)	0.3241 (5)	0.2491 (2)	0.0407 (11)
C11	1.0631 (3)	0.2647 (6)	0.3181 (2)	0.0497 (13)
H11	1.0203	0.1940	0.3376	0.060*
C12	1.1481 (4)	0.3094 (7)	0.3565 (3)	0.0621 (15)
H12	1.1630	0.2698	0.4019	0.075*
C13	1.2124 (4)	0.4155 (7)	0.3268 (3)	0.0709 (17)
H13	1.2707	0.4449	0.3526	0.085*
C14	1.1914 (4)	0.4762 (6)	0.2610 (3)	0.0653 (15)
H14	1.2350	0.5474	0.2426	0.078*
C15	0.4730 (3)	0.3664 (6)	0.2637 (2)	0.0547 (14)
H15A	0.4715	0.4819	0.2589	0.082*
H15B	0.4364	0.3351	0.3021	0.082*
H15C	0.4443	0.3177	0.2209	0.082*
C16	0.5777 (3)	0.3104 (5)	0.2781 (2)	0.0396 (11)
C17	0.7106 (3)	0.2156 (6)	0.3666 (2)	0.0415 (11)
C18	0.6206 (3)	0.2971 (5)	0.3500 (2)	0.0401 (11)
C19	0.5721 (3)	0.3588 (6)	0.4074 (3)	0.0544 (13)
H19	0.5140	0.4160	0.3975	0.065*
C20	0.6067 (4)	0.3380 (6)	0.4755 (3)	0.0588 (14)
H20	0.5727	0.3823	0.5109	0.071*
C21	0.6941 (3)	0.2496 (6)	0.4937 (2)	0.0473 (13)
C22	0.7463 (3)	0.1878 (6)	0.4392 (2)	0.0408 (11)
C23	0.8325 (3)	0.0997 (6)	0.4558 (2)	0.0508 (13)
H23	0.8670	0.0590	0.4199	0.061*
C24	0.8665 (4)	0.0730 (7)	0.5248 (3)	0.0624 (15)
H24	0.9239	0.0145	0.5354	0.075*
C25	0.8152 (4)	0.1332 (7)	0.5791 (3)	0.0692 (17)
H25	0.8382	0.1138	0.6258	0.083*
C26	0.7319 (4)	0.2199 (7)	0.5639 (3)	0.0620 (15)
H26	0.6990	0.2607	0.6006	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0349 (3)	0.0501 (4)	0.0356 (4)	0.0030 (3)	0.0009 (2)	0.0056 (3)
N1	0.033 (2)	0.056 (3)	0.038 (2)	0.010 (2)	−0.0003 (17)	−0.002 (2)
N2	0.041 (2)	0.046 (3)	0.035 (2)	0.0016 (18)	−0.0066 (17)	0.0077 (18)
O1	0.048 (2)	0.091 (3)	0.043 (2)	−0.004 (2)	−0.0062 (17)	−0.0145 (18)
O2	0.0465 (18)	0.047 (2)	0.0471 (19)	0.0065 (17)	−0.0069 (15)	0.0045 (17)
O3	0.0344 (17)	0.063 (2)	0.0422 (19)	0.0012 (16)	0.0013 (14)	0.0161 (16)
O4	0.0446 (18)	0.072 (3)	0.0380 (19)	0.0152 (17)	0.0097 (15)	0.0141 (16)
C1	0.056 (3)	0.048 (3)	0.069 (4)	0.001 (3)	−0.012 (3)	−0.011 (3)
C2	0.045 (3)	0.057 (4)	0.060 (3)	−0.003 (3)	−0.010 (2)	−0.003 (3)
C3	0.058 (3)	0.083 (4)	0.033 (3)	0.022 (3)	0.005 (2)	0.009 (3)
C4	0.044 (3)	0.052 (3)	0.031 (2)	0.019 (2)	0.004 (2)	0.004 (2)
C5	0.035 (3)	0.042 (3)	0.041 (3)	0.009 (2)	0.008 (2)	0.003 (2)
C6	0.041 (3)	0.043 (3)	0.039 (3)	0.010 (2)	0.007 (2)	0.010 (2)
C7	0.058 (3)	0.054 (4)	0.044 (3)	0.011 (3)	0.015 (3)	0.009 (2)
C8	0.063 (4)	0.043 (3)	0.065 (4)	0.001 (3)	0.023 (3)	0.005 (3)
C9	0.042 (3)	0.046 (3)	0.058 (3)	0.003 (2)	0.009 (3)	−0.004 (3)
C10	0.037 (3)	0.043 (3)	0.042 (3)	0.008 (2)	0.004 (2)	0.000 (2)
C11	0.048 (3)	0.053 (3)	0.047 (3)	0.004 (2)	0.000 (2)	0.002 (2)
C12	0.056 (3)	0.073 (4)	0.053 (3)	0.002 (3)	−0.016 (3)	−0.005 (3)
C13	0.053 (4)	0.065 (4)	0.090 (5)	0.001 (3)	−0.013 (3)	−0.018 (4)
C14	0.054 (3)	0.055 (4)	0.088 (4)	−0.009 (3)	0.012 (3)	−0.003 (3)
C15	0.040 (3)	0.057 (4)	0.067 (3)	0.011 (3)	0.005 (2)	0.006 (3)
C16	0.033 (2)	0.037 (3)	0.049 (3)	−0.002 (2)	0.006 (2)	0.008 (2)
C17	0.038 (3)	0.045 (3)	0.042 (3)	−0.009 (2)	0.006 (2)	0.006 (2)
C18	0.043 (3)	0.032 (3)	0.046 (3)	−0.005 (2)	0.007 (2)	0.005 (2)
C19	0.050 (3)	0.050 (3)	0.065 (4)	0.000 (3)	0.012 (3)	−0.007 (3)
C20	0.066 (4)	0.056 (4)	0.056 (4)	−0.012 (3)	0.019 (3)	−0.018 (3)
C21	0.048 (3)	0.050 (4)	0.044 (3)	−0.018 (2)	0.005 (2)	−0.001 (2)
C22	0.041 (3)	0.046 (3)	0.034 (3)	−0.014 (2)	0.001 (2)	0.010 (2)
C23	0.045 (3)	0.063 (4)	0.044 (3)	−0.011 (3)	−0.002 (2)	0.011 (3)
C24	0.052 (3)	0.080 (4)	0.054 (3)	−0.017 (3)	−0.003 (3)	0.010 (3)
C25	0.071 (4)	0.094 (5)	0.040 (3)	−0.031 (4)	−0.011 (3)	0.007 (3)
C26	0.080 (4)	0.064 (4)	0.043 (3)	−0.030 (3)	0.007 (3)	−0.010 (3)

Geometric parameters (Å, º) top

Ni1—O4	1.809 (3)	C10—C11	1.413 (6)
Ni1—O3	1.849 (3)	C11—C12	1.367 (6)
Ni1—N2	1.865 (3)	C11—H11	0.9300
Ni1—N1	1.894 (3)	C12—C13	1.400 (7)
N1—C4	1.295 (5)	C12—H12	0.9300
N1—O1	1.419 (4)	C13—C14	1.355 (7)
N2—C16	1.309 (5)	C13—H13	0.9300
N2—O2	1.430 (4)	C14—H14	0.9300
O1—C1	1.427 (5)	C15—C16	1.508 (5)
O2—C2	1.434 (5)	C15—H15A	0.9600
O3—C5	1.308 (5)	C15—H15B	0.9600
O4—C17	1.292 (5)	C15—H15C	0.9600
C1—C2	1.498 (6)	C16—C18	1.444 (6)
C1—H1A	0.9700	C17—C18	1.415 (6)
C1—H1B	0.9700	C17—C22	1.442 (6)
C2—H2A	0.9700	C18—C19	1.426 (6)
C2—H2B	0.9700	C19—C20	1.349 (6)
C3—C4	1.506 (5)	C19—H19	0.9300
C3—H3A	0.9600	C20—C21	1.419 (7)
C3—H3B	0.9600	C20—H20	0.9300
C3—H3C	0.9600	C21—C26	1.409 (6)
C4—C6	1.459 (6)	C21—C22	1.410 (6)
C5—C6	1.398 (5)	C22—C23	1.398 (6)
C5—C10	1.449 (6)	C23—C24	1.370 (6)
C6—C7	1.411 (6)	C23—H23	0.9300
C7—C8	1.362 (6)	C24—C25	1.395 (7)
C7—H7	0.9300	C24—H24	0.9300
C8—C9	1.415 (6)	C25—C26	1.356 (7)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.407 (6)	C26—H26	0.9300
C9—C14	1.417 (6)

O4—Ni1—O3	83.93 (12)	C9—C10—C5	119.8 (4)
O4—Ni1—N2	90.58 (14)	C11—C10—C5	120.7 (4)
O3—Ni1—N2	168.72 (15)	C12—C11—C10	121.0 (5)
O4—Ni1—N1	168.87 (14)	C12—C11—H11	119.5
O3—Ni1—N1	87.90 (13)	C10—C11—H11	119.5
N2—Ni1—N1	98.73 (14)	C11—C12—C13	119.3 (5)
C4—N1—O1	110.6 (3)	C11—C12—H12	120.3
C4—N1—Ni1	126.4 (3)	C13—C12—H12	120.3
O1—N1—Ni1	122.7 (3)	C14—C13—C12	121.2 (5)
C16—N2—O2	112.3 (3)	C14—C13—H13	119.4
C16—N2—Ni1	130.0 (3)	C12—C13—H13	119.4
O2—N2—Ni1	117.0 (2)	C13—C14—C9	120.8 (5)
N1—O1—C1	111.5 (3)	C13—C14—H14	119.6
N2—O2—C2	110.4 (3)	C9—C14—H14	119.6
C5—O3—Ni1	118.4 (3)	C16—C15—H15A	109.5
C17—O4—Ni1	130.0 (3)	C16—C15—H15B	109.5
O1—C1—C2	110.7 (4)	H15A—C15—H15B	109.5
O1—C1—H1A	109.5	C16—C15—H15C	109.5
C2—C1—H1A	109.5	H15A—C15—H15C	109.5
O1—C1—H1B	109.5	H15B—C15—H15C	109.5
C2—C1—H1B	109.5	N2—C16—C18	120.5 (4)
H1A—C1—H1B	108.1	N2—C16—C15	119.9 (4)
O2—C2—C1	112.1 (4)	C18—C16—C15	119.5 (4)
O2—C2—H2A	109.2	O4—C17—C18	123.1 (4)
C1—C2—H2A	109.2	O4—C17—C22	116.8 (4)
O2—C2—H2B	109.2	C18—C17—C22	120.1 (4)
C1—C2—H2B	109.2	C17—C18—C19	117.2 (4)
H2A—C2—H2B	107.9	C17—C18—C16	121.2 (4)
C4—C3—H3A	109.5	C19—C18—C16	121.5 (4)
C4—C3—H3B	109.5	C20—C19—C18	123.0 (5)
H3A—C3—H3B	109.5	C20—C19—H19	118.5
C4—C3—H3C	109.5	C18—C19—H19	118.5
H3A—C3—H3C	109.5	C19—C20—C21	120.9 (5)
H3B—C3—H3C	109.5	C19—C20—H20	119.5
N1—C4—C6	119.1 (4)	C21—C20—H20	119.5
N1—C4—C3	121.2 (4)	C26—C21—C22	118.0 (5)
C6—C4—C3	119.6 (4)	C26—C21—C20	123.3 (5)
O3—C5—C6	123.6 (4)	C22—C21—C20	118.7 (4)
O3—C5—C10	116.9 (4)	C23—C22—C21	119.8 (4)
C6—C5—C10	119.5 (4)	C23—C22—C17	120.3 (4)
C5—C6—C7	118.5 (4)	C21—C22—C17	119.9 (4)
C5—C6—C4	119.1 (4)	C24—C23—C22	120.3 (5)
C7—C6—C4	121.9 (4)	C24—C23—H23	119.8
C8—C7—C6	122.9 (4)	C22—C23—H23	119.8
C8—C7—H7	118.5	C23—C24—C25	120.3 (5)
C6—C7—H7	118.5	C23—C24—H24	119.9
C7—C8—C9	120.0 (5)	C25—C24—H24	119.9
C7—C8—H8	120.0	C26—C25—C24	120.2 (5)
C9—C8—H8	120.0	C26—C25—H25	119.9
C10—C9—C8	119.2 (4)	C24—C25—H25	119.9
C10—C9—C14	118.3 (5)	C25—C26—C21	121.4 (5)
C8—C9—C14	122.5 (5)	C25—C26—H26	119.3
C9—C10—C11	119.4 (4)	C21—C26—H26	119.3

O4—Ni1—N1—C4	−77.6 (9)	C14—C9—C10—C5	179.4 (4)
O3—Ni1—N1—C4	−34.9 (4)	O3—C5—C10—C9	179.2 (4)
N2—Ni1—N1—C4	135.9 (4)	C6—C5—C10—C9	0.4 (6)
O4—Ni1—N1—O1	95.3 (8)	O3—C5—C10—C11	−2.4 (6)
O3—Ni1—N1—O1	138.1 (3)	C6—C5—C10—C11	178.8 (4)
N2—Ni1—N1—O1	−51.1 (3)	C9—C10—C11—C12	−0.8 (7)
O4—Ni1—N2—C16	18.8 (4)	C5—C10—C11—C12	−179.2 (4)
O3—Ni1—N2—C16	−41.9 (9)	C10—C11—C12—C13	−0.1 (7)
N1—Ni1—N2—C16	−167.3 (4)	C11—C12—C13—C14	0.9 (8)
O4—Ni1—N2—O2	−171.9 (3)	C12—C13—C14—C9	−0.7 (8)
O3—Ni1—N2—O2	127.5 (6)	C10—C9—C14—C13	−0.2 (7)
N1—Ni1—N2—O2	2.0 (3)	C8—C9—C14—C13	178.3 (5)
C4—N1—O1—C1	170.0 (4)	O2—N2—C16—C18	−176.5 (4)
Ni1—N1—O1—C1	−3.9 (5)	Ni1—N2—C16—C18	−6.7 (6)
C16—N2—O2—C2	−110.3 (4)	O2—N2—C16—C15	6.5 (6)
Ni1—N2—O2—C2	78.6 (3)	Ni1—N2—C16—C15	176.3 (3)
O4—Ni1—O3—C5	−136.0 (3)	Ni1—O4—C17—C18	14.1 (6)
N2—Ni1—O3—C5	−74.8 (8)	Ni1—O4—C17—C22	−166.5 (3)
N1—Ni1—O3—C5	51.5 (3)	O4—C17—C18—C19	−176.3 (4)
O3—Ni1—O4—C17	147.7 (4)	C22—C17—C18—C19	4.3 (6)
N2—Ni1—O4—C17	−22.5 (4)	O4—C17—C18—C16	6.6 (7)
N1—Ni1—O4—C17	−169.4 (7)	C22—C17—C18—C16	−172.8 (4)
N1—O1—C1—C2	87.7 (4)	N2—C16—C18—C17	−9.8 (7)
N2—O2—C2—C1	−62.0 (5)	C15—C16—C18—C17	167.3 (4)
O1—C1—C2—O2	−48.8 (5)	N2—C16—C18—C19	173.2 (4)
O1—N1—C4—C6	−170.9 (4)	C15—C16—C18—C19	−9.8 (7)
Ni1—N1—C4—C6	2.8 (6)	C17—C18—C19—C20	−2.1 (7)
O1—N1—C4—C3	6.2 (6)	C16—C18—C19—C20	175.0 (4)
Ni1—N1—C4—C3	179.9 (3)	C18—C19—C20—C21	−1.0 (7)
Ni1—O3—C5—C6	−39.8 (5)	C19—C20—C21—C26	−178.0 (4)
Ni1—O3—C5—C10	141.4 (3)	C19—C20—C21—C22	2.0 (7)
O3—C5—C6—C7	−179.5 (4)	C26—C21—C22—C23	0.2 (6)
C10—C5—C6—C7	−0.7 (6)	C20—C21—C22—C23	−179.8 (4)
O3—C5—C6—C4	−6.9 (6)	C26—C21—C22—C17	−179.8 (4)
C10—C5—C6—C4	171.9 (4)	C20—C21—C22—C17	0.2 (6)
N1—C4—C6—C5	26.4 (6)	O4—C17—C22—C23	−2.9 (6)
C3—C4—C6—C5	−150.8 (4)	C18—C17—C22—C23	176.6 (4)
N1—C4—C6—C7	−161.3 (4)	O4—C17—C22—C21	177.1 (4)
C3—C4—C6—C7	21.6 (6)	C18—C17—C22—C21	−3.4 (6)
C5—C6—C7—C8	−0.1 (7)	C21—C22—C23—C24	0.1 (7)
C4—C6—C7—C8	−172.5 (4)	C17—C22—C23—C24	−179.9 (4)
C6—C7—C8—C9	1.3 (7)	C22—C23—C24—C25	0.2 (7)
C7—C8—C9—C10	−1.6 (7)	C23—C24—C25—C26	−0.7 (8)
C7—C8—C9—C14	179.9 (5)	C24—C25—C26—C21	1.0 (8)
C8—C9—C10—C11	−177.6 (4)	C22—C21—C26—C25	−0.7 (7)
C14—C9—C10—C11	1.0 (6)	C20—C21—C26—C25	179.2 (5)
C8—C9—C10—C5	0.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O3ⁱ	0.96	2.45	3.152 (6)	130
C3—H3C···Cg1ⁱⁱ	0.97	3.17	4.127 (3)	172
C15—H15A···Cg2ⁱⁱⁱ	0.96	3.53	4.398 (3)	152

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

Experimental details

Crystal data
Chemical formula	[Ni(C₂₆H₂₂N₂O₄)]
M_r	485.17
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	13.6975 (13), 8.2711 (10), 19.049 (2)
β (°)	95.346 (1)
V (Å³)	2148.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.43 × 0.16 × 0.06

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.688, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	10414, 3782, 2179
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.126, 1.02
No. of reflections	3782
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.38

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O3ⁱ	0.96	2.45	3.152 (6)	129.7
C3—H3C···Cg1ⁱⁱ	0.97	3.165	4.127 (3)	171.99
C15—H15A···Cg2ⁱⁱⁱ	0.96	3.529	4.398 (3)	151.74

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

Acknowledgements

The authors acknowledge finanical support from the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University.

References

Akine, S., Takanori, T., Taniguchi, T. & Nabeshima, T. (2005). Inorg. Chem. 44, 3270–3274. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Dong, W. K., Sun, Y. X., Zhang, Y. P., Li, L., He, X. N. & Tang, X. L. (2009b). Inorg. Chim. Acta, 362, 117–124. Web of Science CSD CrossRef CAS Google Scholar
Dong, W.-K., Wu, J.-C., Yao, J., Gong, S.-S. & Tong, J.-F. (2009c). Acta Cryst. E65, m802. Web of Science CSD CrossRef IUCr Journals Google Scholar
Katsuki, T. (1995). Coord. Chem. Rev. 140, 189–214. CrossRef CAS Web of Science Google Scholar
Ray, M. S., Mukhopadhyay, G. M., Drew, M. G. B., Lu, T. H., Chaudhuri, S. & Ghosh, A. (2003). Inorg. Chem. Commun. 6, 961–965. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 65| Part 7| July 2009| Page m803

doi:10.1107/S1600536809023149

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

{2,2′-[1,1′-(Ethyl­ene­dioxy­di­nitrilo)di­ethyl­­idyne]di-1-naphtholato}nickel(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{2,2′-[1,1′-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphtholato}nickel(II)