Bis{2-[3-(dimethyl­amino)propyl­imino­meth­yl]-6-methoxy­phenolato-κ3N,N′,O1}nickel(II)

Guo, H.-M.; Lin, H.

doi:10.1107/S1600536808020497

metal-organic compounds

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Volume 64| Part 8| August 2008| Page m1009

doi:10.1107/S1600536808020497

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Bis{2-[3-(dimethylamino)propyliminomethyl]-6-methoxyphenolato-κ³N,N′,O¹}nickel(II)

Hang-Ming Guo ^a and Hong Lin ^a ^*

^aJinhua Professional Technical College, Jinhua, Zhejiang Province 321017, People's Republic of China
^*Correspondence e-mail: jh_ll@126.com

(Received 19 May 2008; accepted 3 July 2008; online 9 July 2008)

The centrosymmetric title complex, [Ni(C₁₃H₁₉N₂O₂)₂], is a mononuclear nickel(II) complex. The Ni^II atom is coordinated by four N atoms and two O atoms of two deprotonated Schiff base ligands, forming a slightly distorted octahedral coordination configuration, in which the tertiary N atoms occupy the axial positions.

Related literature

For related literature, see: Choudhury et al. (2001 ); Das et al. (1997 ); Davies et al. (1973 ); Feng (2003 ); Li & Wang (2007 ); Pariya et al. (1995 ).

Experimental

Crystal data

[Ni(C₁₃H₁₉N₂O₂)₂]
M_r = 529.31
Triclinic, $[P \overline 1]$
a = 7.4758 (15) Å
b = 8.5571 (17) Å
c = 10.995 (2) Å
α = 78.36 (3)°
β = 73.98 (3)°
γ = 73.73 (3)°
V = 643.0 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 296 (2) K
0.35 × 0.28 × 0.26 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.766, T_max = 0.814
10449 measured reflections
2937 independent reflections
2727 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.077
S = 1.00
2937 reflections
160 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020497/at2571sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020497/at2571Isup2.hkl

checkCIF report

Comment top

There is considerable interest in the synthesis of multidentate Schiff base ligands for their versatile coordination behavior to metal ions and wide application in biological systems (Das et al., 1997). Metal complexes with tetradentate N₂O₂ and tridentate N₂O Schiff base ligands derived from salicylaldehyde have been well studied in the past, such as [Ni(C₁₂H₁₈N₂O₂)₂Cl₂] (Feng, 2003), [Mn(C₁₈H₁₇N₂O₄)] (Davies et al., 1973) and [Ni(Me₂NCH₂CH₂CH₂N=CHC₆H₄O)₂] (Choudhury et al., 2001). The title complex, [Ni(C₁₃H₁₉N₂O₂)₂], has a crystallograpic center with the Ni atom situated at the center of (1/2, 0, 1/2). As illustrated in Fig. 1, the center Ni^II ion is octahedrally coordinated by two tridentate chelate ligands in a meridional arrangement resulting in a slightly distorted octahedral geometry. The equatorial plane is formed by two imine nitrogen atoms (N1 and N1ⁱ) and two deprotonated phenolate oxygen atoms (O1 and O1ⁱ) with the deviation of the metal ion of 0.003 (1) Å. The axial positions are occupied by the tertiary nitrogen atoms (N2 and N2ⁱ). Like other reported structures, (Li & Wang, 2007; Pariya et al., 1995), the axial Ni(1)—N(2) distance (2.308 (1) Å) is larger than the equatorial Ni(1)—N(1) distance (2.055 (1) Å). The bond angles around the Ni^II ion also deviate slightly from the ideal octahedron geometry. Angles involving the atoms in the trans positions are 180° but those invoving the cis-atoms vary from 81.07 (6)–98.96 (6)°.

Related literature top

For related literature, see: Choudhury et al. (2001); Das et al. (1997); Davies et al. (1973); Feng (2003); Li & Wang (2007); Pariya et al. (1995).

Experimental top

3-methoxysalicylaldehyde (2.0 mmol) and 3-dimenthylaminopropylamine (2.0 mmol) in 15 ml of methyl alcohol were stirred for 4 h. NiCl₂^.4H₂O (1.0 mmol) was added and stirred for 10 h. The resulting solution was placed in a refrigerator at 263 K for 10 days, and the crystals were filtered off, giving orange crystals of the title complex for X-ray analysis.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme, displacement ellipsoids are shown at the 30% probability level. [Symmetry codes: (i) -x + 1,-y,-z + 1]

Bis{2-[3-(dimethylamino)propyliminomethyl]-6-methoxyphenolato-κ³N,N',O¹}nickel(II) top

Crystal data top

[Ni(C₁₃H₁₉N₂O₂)₂]	Z = 1
M_r = 529.31	F(000) = 282
Triclinic, P1	D_x = 1.367 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4758 (15) Å	Cell parameters from 10453 reflections
b = 8.5571 (17) Å	θ = 1.9–27.5°
c = 10.995 (2) Å	µ = 0.79 mm⁻¹
α = 78.36 (3)°	T = 296 K
β = 73.98 (3)°	Block, orange
γ = 73.73 (3)°	0.35 × 0.28 × 0.26 mm
V = 643.0 (2) Å³

Data collection top

Bruker APEXII area-detector diffractometer	2937 independent reflections
Radiation source: fine-focus sealed tube	2727 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.766, T_max = 0.814	k = −10→11
10449 measured reflections	l = −14→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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0466P)² + 0.1331P] where P = (F_o² + 2F_c²)/3
2937 reflections	(Δ/σ)_max < 0.001
160 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

[Ni(C₁₃H₁₉N₂O₂)₂]	γ = 73.73 (3)°
M_r = 529.31	V = 643.0 (2) Å³
Triclinic, P1	Z = 1
a = 7.4758 (15) Å	Mo Kα radiation
b = 8.5571 (17) Å	µ = 0.79 mm⁻¹
c = 10.995 (2) Å	T = 296 K
α = 78.36 (3)°	0.35 × 0.28 × 0.26 mm
β = 73.98 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	2937 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2727 reflections with I > 2σ(I)
T_min = 0.766, T_max = 0.814	R_int = 0.020
10449 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.00	Δρ_max = 0.32 e Å⁻³
2937 reflections	Δρ_min = −0.17 e Å⁻³
160 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	0.5000	0.0000	0.5000	0.03138 (10)
O1	0.57408 (15)	0.09660 (13)	0.62529 (9)	0.0365 (2)
O2	0.73982 (18)	0.1105 (2)	0.80263 (12)	0.0627 (4)
N1	0.22745 (17)	0.14317 (15)	0.55226 (12)	0.0371 (3)
N2	0.5262 (2)	0.22458 (15)	0.34548 (12)	0.0399 (3)
C1	0.4656 (2)	0.17196 (17)	0.71970 (13)	0.0346 (3)
C2	0.5492 (2)	0.1879 (2)	0.81787 (15)	0.0439 (4)
C3	0.4433 (3)	0.2733 (2)	0.91789 (16)	0.0561 (5)
H3A	0.5018	0.2827	0.9797	0.067*
C4	0.2490 (3)	0.3462 (3)	0.92760 (17)	0.0611 (5)
H4A	0.1790	0.4061	0.9944	0.073*
C5	0.1622 (3)	0.3292 (2)	0.83891 (16)	0.0502 (4)
H5A	0.0322	0.3771	0.8463	0.060*
C6	0.2657 (2)	0.24013 (18)	0.73553 (14)	0.0391 (3)
C7	0.1632 (2)	0.22884 (19)	0.64567 (15)	0.0404 (3)
H7A	0.0370	0.2900	0.6562	0.048*
C8	0.1073 (2)	0.1771 (2)	0.46023 (16)	0.0471 (4)
H8A	−0.0265	0.2136	0.5026	0.057*
H8B	0.1226	0.0780	0.4246	0.057*
C9	0.1672 (3)	0.3098 (2)	0.35454 (18)	0.0560 (5)
H9A	0.1508	0.4073	0.3926	0.067*
H9B	0.0809	0.3376	0.2976	0.067*
C10	0.3716 (3)	0.2666 (2)	0.27522 (15)	0.0496 (4)
H10A	0.3850	0.1740	0.2322	0.059*
H10B	0.3914	0.3588	0.2098	0.059*
C11	0.7109 (3)	0.1849 (2)	0.25224 (16)	0.0520 (4)
H11A	0.7230	0.2777	0.1876	0.078*
H11B	0.7164	0.0922	0.2135	0.078*
H11C	0.8137	0.1590	0.2950	0.078*
C12	0.5251 (3)	0.3671 (2)	0.40162 (16)	0.0506 (4)
H12A	0.5361	0.4588	0.3357	0.076*
H12B	0.6311	0.3405	0.4414	0.076*
H12C	0.4073	0.3950	0.4644	0.076*
C13	0.8151 (3)	0.0722 (3)	0.9111 (2)	0.0726 (6)
H13A	0.9487	0.0188	0.8885	0.109*
H13B	0.7480	0.0003	0.9744	0.109*
H13C	0.8001	0.1714	0.9449	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03755 (15)	0.03032 (15)	0.02764 (14)	−0.00398 (10)	−0.01031 (10)	−0.00902 (9)
O1	0.0411 (5)	0.0390 (5)	0.0316 (5)	−0.0064 (4)	−0.0097 (4)	−0.0126 (4)
O2	0.0516 (7)	0.1037 (11)	0.0382 (6)	−0.0142 (7)	−0.0142 (5)	−0.0222 (7)
N1	0.0390 (6)	0.0359 (6)	0.0359 (6)	−0.0029 (5)	−0.0125 (5)	−0.0069 (5)
N2	0.0574 (8)	0.0333 (6)	0.0321 (6)	−0.0133 (6)	−0.0123 (5)	−0.0053 (5)
C1	0.0487 (8)	0.0283 (7)	0.0271 (6)	−0.0097 (6)	−0.0087 (6)	−0.0042 (5)
C2	0.0555 (9)	0.0490 (9)	0.0309 (7)	−0.0158 (7)	−0.0100 (6)	−0.0088 (6)
C3	0.0760 (12)	0.0648 (12)	0.0332 (8)	−0.0167 (10)	−0.0136 (8)	−0.0180 (8)
C4	0.0814 (13)	0.0576 (11)	0.0378 (9)	−0.0024 (10)	−0.0058 (8)	−0.0231 (8)
C5	0.0587 (10)	0.0421 (9)	0.0403 (8)	0.0025 (7)	−0.0056 (7)	−0.0134 (7)
C6	0.0506 (8)	0.0301 (7)	0.0328 (7)	−0.0034 (6)	−0.0077 (6)	−0.0072 (6)
C7	0.0409 (7)	0.0342 (7)	0.0404 (8)	0.0014 (6)	−0.0091 (6)	−0.0078 (6)
C8	0.0410 (8)	0.0518 (10)	0.0497 (9)	0.0008 (7)	−0.0196 (7)	−0.0135 (8)
C9	0.0695 (11)	0.0444 (9)	0.0560 (10)	0.0036 (8)	−0.0367 (9)	−0.0040 (8)
C10	0.0780 (12)	0.0395 (8)	0.0349 (8)	−0.0130 (8)	−0.0244 (8)	0.0008 (6)
C11	0.0709 (11)	0.0474 (9)	0.0374 (8)	−0.0225 (8)	−0.0044 (8)	−0.0050 (7)
C12	0.0792 (12)	0.0354 (8)	0.0430 (9)	−0.0203 (8)	−0.0159 (8)	−0.0067 (7)
C13	0.0625 (12)	0.1093 (19)	0.0514 (11)	−0.0211 (12)	−0.0217 (9)	−0.0104 (11)

Geometric parameters (Å, º) top

Ni1—O1	2.0061 (11)	C5—C6	1.416 (2)
Ni1—O1ⁱ	2.0061 (11)	C5—H5A	0.9300
Ni1—N1	2.0547 (14)	C6—C7	1.439 (2)
Ni1—N1ⁱ	2.0547 (14)	C7—H7A	0.9300
Ni1—N2ⁱ	2.3081 (15)	C8—C9	1.518 (3)
Ni1—N2	2.3081 (15)	C8—H8A	0.9700
O1—C1	1.2899 (17)	C8—H8B	0.9700
O2—C2	1.372 (2)	C9—C10	1.520 (3)
O2—C13	1.399 (2)	C9—H9A	0.9700
N1—C7	1.287 (2)	C9—H9B	0.9700
N1—C8	1.467 (2)	C10—H10A	0.9700
N2—C12	1.471 (2)	C10—H10B	0.9700
N2—C11	1.473 (2)	C11—H11A	0.9600
N2—C10	1.487 (2)	C11—H11B	0.9600
C1—C6	1.418 (2)	C11—H11C	0.9600
C1—C2	1.433 (2)	C12—H12A	0.9600
C2—C3	1.375 (2)	C12—H12B	0.9600
C3—C4	1.394 (3)	C12—H12C	0.9600
C3—H3A	0.9300	C13—H13A	0.9600
C4—C5	1.361 (3)	C13—H13B	0.9600
C4—H4A	0.9300	C13—H13C	0.9600

O1—Ni1—O1ⁱ	180.0	C5—C6—C7	117.77 (15)
O1—Ni1—N1	88.00 (5)	C1—C6—C7	122.05 (13)
O1ⁱ—Ni1—N1	92.00 (5)	N1—C7—C6	126.96 (14)
O1—Ni1—N1ⁱ	92.00 (5)	N1—C7—H7A	116.5
O1ⁱ—Ni1—N1ⁱ	88.00 (5)	C6—C7—H7A	116.5
N1—Ni1—N1ⁱ	180.00 (7)	N1—C8—C9	108.79 (14)
O1—Ni1—N2ⁱ	87.10 (5)	N1—C8—H8A	109.9
O1ⁱ—Ni1—N2ⁱ	92.90 (5)	C9—C8—H8A	109.9
N1—Ni1—N2ⁱ	98.96 (6)	N1—C8—H8B	109.9
N1ⁱ—Ni1—N2ⁱ	81.04 (6)	C9—C8—H8B	109.9
O1—Ni1—N2	92.90 (5)	H8A—C8—H8B	108.3
O1ⁱ—Ni1—N2	87.10 (5)	C8—C9—C10	115.86 (14)
N1—Ni1—N2	81.04 (6)	C8—C9—H9A	108.3
N1ⁱ—Ni1—N2	98.96 (6)	C10—C9—H9A	108.3
N2ⁱ—Ni1—N2	180.00 (5)	C8—C9—H9B	108.3
C1—O1—Ni1	129.01 (10)	C10—C9—H9B	108.3
C2—O2—C13	117.24 (15)	H9A—C9—H9B	107.4
C7—N1—C8	116.00 (13)	N2—C10—C9	116.40 (13)
C7—N1—Ni1	126.39 (11)	N2—C10—H10A	108.2
C8—N1—Ni1	116.42 (10)	C9—C10—H10A	108.2
C12—N2—C11	107.24 (14)	N2—C10—H10B	108.2
C12—N2—C10	110.49 (14)	C9—C10—H10B	108.2
C11—N2—C10	107.71 (13)	H10A—C10—H10B	107.3
C12—N2—Ni1	110.96 (10)	N2—C11—H11A	109.5
C11—N2—Ni1	108.89 (10)	N2—C11—H11B	109.5
C10—N2—Ni1	111.39 (10)	H11A—C11—H11B	109.5
O1—C1—C6	124.80 (13)	N2—C11—H11C	109.5
O1—C1—C2	118.76 (14)	H11A—C11—H11C	109.5
C6—C1—C2	116.44 (14)	H11B—C11—H11C	109.5
O2—C2—C3	124.23 (16)	N2—C12—H12A	109.5
O2—C2—C1	114.18 (14)	N2—C12—H12B	109.5
C3—C2—C1	121.60 (16)	H12A—C12—H12B	109.5
C2—C3—C4	120.66 (17)	N2—C12—H12C	109.5
C2—C3—H3A	119.7	H12A—C12—H12C	109.5
C4—C3—H3A	119.7	H12B—C12—H12C	109.5
C5—C4—C3	119.69 (16)	O2—C13—H13A	109.5
C5—C4—H4A	120.2	O2—C13—H13B	109.5
C3—C4—H4A	120.2	H13A—C13—H13B	109.5
C4—C5—C6	121.33 (17)	O2—C13—H13C	109.5
C4—C5—H5A	119.3	H13A—C13—H13C	109.5
C6—C5—H5A	119.3	H13B—C13—H13C	109.5
C5—C6—C1	120.12 (15)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₃H₁₉N₂O₂)₂]
M_r	529.31
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.4758 (15), 8.5571 (17), 10.995 (2)
α, β, γ (°)	78.36 (3), 73.98 (3), 73.73 (3)
V (Å³)	643.0 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.35 × 0.28 × 0.26

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.766, 0.814
No. of measured, independent and observed [I > 2σ(I)] reflections	10449, 2937, 2727
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.077, 1.00
No. of reflections	2937
No. of parameters	160
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.17

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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