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The title complex, [Ni(C12H17N2O2)2], possesses a crystallographically imposed center of symmetry occupied by the NiII ion. Each 2-meth­oxy-6-[3-(methyl­amino)propyl­imino­meth­yl]­phenolate ligand coordinates the Ni atom in a tridentate mode [Ni-O = 2.0356 (18) Å, and Ni-N = 2.048 (2) and 2.184 (2) Å], resulting in a distorted octa­hedral coordination geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048155/cv2312sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048155/cv2312Isup2.hkl
Contains datablock I

CCDC reference: 667111

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.095
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.77 Ratio PLAT245_ALERT_2_C U(iso) H2 Smaller than U(eq) N2 by ... 0.01 AngSq PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2 ... ?
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of N2 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In continuation of our study of Ni complexes with Shiff base ligands (Tang, 2006), we report here the crystal structure of the title compound, NiL2, where HL is a Shiff base 2-methoxy-6-[(3-methylaminopropylimino)methyl]phenol.

The title complex [Ni(C12H17N2O2)2] is a centrosymmetric mononuclear nickel(II) complex (Fig. 1). The Ni atom, lying on the inversion centre, is six-coordinated by two phenolic oxygen atoms, two imine N atoms and two amine N atoms from two Schiff base ligands, forming an octahedral coordination geometry. The coordinative bond lengths and angles are within normal ranges and comparable with those observed in similar nickel(II) complexes (Zhu et al., 2004; Liu et al., 2006; Zhang, 2006; Diao, 2007; Diao, Li et al., 2007).

Related literature top

For related crystal structures, see: Zhu et al. (2004); Liu et al. (2006); Zhang (2006); Tang (2006); Diao (2007); Diao et al. (2007).

Experimental top

3-Methoxy-2-hydroxybenzaldehyde (0.2 mmol, 30.5 mg) and N-methyl-1,3-diaminopropane (0.2 mmol, 17.6 mg) were dissolved in a methanol solution (10 ml). To the mixture was added an aqueous solution (1 ml) of nickel(II) chloride hexahydrate (0.1 mmol, 23.8 mg). The final mixture was stirred at room temperature for 30 min, resulting in a green solution. The solution was allowed to stand in air for three days, yielding green block-shaped crystals of the title complex.

Refinement top

H2 attached to N2 was located from a difference Fourier map and refined isotropically, with N–H distance restrained to 0.90 (1) Å. C-bound H atoms were geometrically positioned, with C–H = 0.93–0.97 Å, and refined as riding, with Uiso(H) set to 1.2Ueq(C) or 1.5Ueq(methyl C).

Structure description top

In continuation of our study of Ni complexes with Shiff base ligands (Tang, 2006), we report here the crystal structure of the title compound, NiL2, where HL is a Shiff base 2-methoxy-6-[(3-methylaminopropylimino)methyl]phenol.

The title complex [Ni(C12H17N2O2)2] is a centrosymmetric mononuclear nickel(II) complex (Fig. 1). The Ni atom, lying on the inversion centre, is six-coordinated by two phenolic oxygen atoms, two imine N atoms and two amine N atoms from two Schiff base ligands, forming an octahedral coordination geometry. The coordinative bond lengths and angles are within normal ranges and comparable with those observed in similar nickel(II) complexes (Zhu et al., 2004; Liu et al., 2006; Zhang, 2006; Diao, 2007; Diao, Li et al., 2007).

For related crystal structures, see: Zhu et al. (2004); Liu et al. (2006); Zhang (2006); Tang (2006); Diao (2007); Diao et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms are related with the labelled ones by symmetry code (-x, 1 - y, 1 - z).
Bis{2-methoxy-6-[3-(methylamino)propyliminomethyl]phenolato}nickel(II) top
Crystal data top
[Ni(C12H17N2O2)2]Dx = 1.440 Mg m3
Mr = 501.26Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 1621 reflections
a = 8.762 (3) Åθ = 2.3–24.5°
b = 15.297 (5) ŵ = 0.88 mm1
c = 17.247 (5) ÅT = 298 K
V = 2311.5 (12) Å3Block, green
Z = 40.23 × 0.21 × 0.18 mm
F(000) = 1064
Data collection top
Bruker SMART CCD area-detector
diffractometer
2150 independent reflections
Radiation source: fine-focus sealed tube1361 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 108
Tmin = 0.824, Tmax = 0.858k = 1618
11114 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0401P)2 + 0.8022P]
where P = (Fo2 + 2Fc2)/3
2150 reflections(Δ/σ)max < 0.001
157 parametersΔρmax = 0.27 e Å3
1 restraintΔρmin = 0.33 e Å3
Crystal data top
[Ni(C12H17N2O2)2]V = 2311.5 (12) Å3
Mr = 501.26Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 8.762 (3) ŵ = 0.88 mm1
b = 15.297 (5) ÅT = 298 K
c = 17.247 (5) Å0.23 × 0.21 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2150 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1361 reflections with I > 2σ(I)
Tmin = 0.824, Tmax = 0.858Rint = 0.058
11114 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0351 restraint
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.27 e Å3
2150 reflectionsΔρmin = 0.33 e Å3
157 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
xyzUiso*/Ueq
Ni10.00000.50000.50000.02728 (16)
O10.1095 (2)0.46563 (12)0.40048 (10)0.0328 (5)
O20.2997 (2)0.38059 (13)0.30828 (12)0.0461 (6)
N10.0197 (3)0.62692 (15)0.46346 (14)0.0321 (6)
N20.2128 (3)0.50609 (15)0.43420 (14)0.0345 (6)
C10.2275 (3)0.60365 (18)0.37150 (15)0.0305 (7)
C20.2130 (3)0.51145 (18)0.36524 (15)0.0289 (6)
C30.3187 (3)0.46964 (19)0.31390 (16)0.0332 (7)
C40.4273 (4)0.5157 (2)0.27416 (16)0.0416 (8)
H40.49410.48630.24130.050*
C50.4391 (4)0.6059 (2)0.28230 (18)0.0452 (8)
H50.51420.63660.25550.054*
C60.3404 (3)0.6492 (2)0.32953 (16)0.0394 (8)
H60.34740.70960.33420.047*
C70.1176 (3)0.65523 (19)0.41434 (16)0.0345 (7)
H70.11800.71520.40520.041*
C80.1012 (3)0.6874 (2)0.48796 (17)0.0419 (8)
H8A0.06900.74730.47920.050*
H8B0.12140.68020.54290.050*
C90.2454 (3)0.6683 (2)0.44154 (19)0.0470 (8)
H9A0.32090.71260.45380.056*
H9B0.22160.67360.38680.056*
C100.3154 (3)0.5793 (2)0.45555 (18)0.0413 (8)
H10A0.34190.57420.51000.050*
H10B0.40890.57460.42570.050*
C110.2999 (4)0.4240 (2)0.42889 (19)0.0492 (9)
H11A0.34470.41100.47840.074*
H11B0.23280.37730.41400.074*
H11C0.37910.43020.39080.074*
C120.3999 (4)0.3351 (2)0.25727 (19)0.0553 (9)
H12A0.39260.35980.20620.083*
H12B0.37180.27450.25550.083*
H12C0.50280.34040.27570.083*
H20.174 (3)0.5177 (15)0.3878 (8)0.022 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0236 (3)0.0302 (3)0.0281 (3)0.0015 (2)0.0041 (2)0.0008 (2)
O10.0306 (11)0.0354 (11)0.0325 (11)0.0025 (9)0.0083 (10)0.0001 (9)
O20.0472 (14)0.0403 (13)0.0508 (13)0.0030 (10)0.0197 (11)0.0089 (11)
N10.0326 (15)0.0325 (13)0.0314 (12)0.0035 (11)0.0053 (12)0.0016 (11)
N20.0309 (14)0.0408 (14)0.0318 (13)0.0003 (12)0.0030 (12)0.0002 (12)
C10.0284 (16)0.0387 (17)0.0244 (14)0.0011 (13)0.0005 (13)0.0024 (13)
C20.0241 (15)0.0426 (18)0.0201 (13)0.0000 (14)0.0029 (12)0.0025 (12)
C30.0324 (17)0.0400 (17)0.0271 (15)0.0022 (14)0.0011 (14)0.0014 (13)
C40.0363 (18)0.058 (2)0.0307 (16)0.0054 (16)0.0105 (15)0.0014 (15)
C50.041 (2)0.051 (2)0.0430 (18)0.0102 (17)0.0111 (16)0.0094 (16)
C60.0387 (18)0.0422 (18)0.0372 (17)0.0031 (15)0.0054 (15)0.0069 (15)
C70.0384 (18)0.0318 (16)0.0332 (15)0.0019 (14)0.0047 (15)0.0018 (13)
C80.043 (2)0.0331 (17)0.0495 (19)0.0055 (15)0.0078 (17)0.0031 (14)
C90.0404 (19)0.046 (2)0.055 (2)0.0172 (16)0.0023 (17)0.0016 (17)
C100.0263 (17)0.055 (2)0.0428 (18)0.0085 (15)0.0007 (15)0.0007 (16)
C110.045 (2)0.052 (2)0.051 (2)0.0074 (17)0.0110 (17)0.0031 (16)
C120.063 (2)0.052 (2)0.052 (2)0.0125 (18)0.019 (2)0.0094 (17)
Geometric parameters (Å, º) top
Ni1—O1i2.0356 (18)C4—H40.9300
Ni1—O12.0356 (18)C5—C61.360 (4)
Ni1—N12.048 (2)C5—H50.9300
Ni1—N1i2.048 (2)C6—H60.9300
Ni1—N2i2.184 (2)C7—H70.9300
Ni1—N22.184 (2)C8—C91.524 (4)
O1—C21.297 (3)C8—H8A0.9700
O2—C31.376 (3)C8—H8B0.9700
O2—C121.424 (3)C9—C101.513 (4)
N1—C71.281 (3)C9—H9A0.9700
N1—C81.469 (3)C9—H9B0.9700
N2—C111.473 (4)C10—H10A0.9700
N2—C101.483 (4)C10—H10B0.9700
N2—H20.886 (10)C11—H11A0.9600
C1—C61.410 (4)C11—H11B0.9600
C1—C21.420 (4)C11—H11C0.9600
C1—C71.448 (4)C12—H12A0.9600
C2—C31.432 (4)C12—H12B0.9600
C3—C41.368 (4)C12—H12C0.9600
C4—C51.392 (4)
O1i—Ni1—O1180.0C6—C5—H5120.1
O1i—Ni1—N193.12 (8)C4—C5—H5120.1
O1—Ni1—N186.88 (8)C5—C6—C1120.9 (3)
O1i—Ni1—N1i86.88 (8)C5—C6—H6119.6
O1—Ni1—N1i93.12 (8)C1—C6—H6119.6
N1—Ni1—N1i180.0N1—C7—C1126.8 (3)
O1i—Ni1—N2i88.59 (8)N1—C7—H7116.6
O1—Ni1—N2i91.41 (8)C1—C7—H7116.6
N1—Ni1—N2i97.37 (9)N1—C8—C9109.0 (2)
N1i—Ni1—N2i82.63 (9)N1—C8—H8A109.9
O1i—Ni1—N291.41 (8)C9—C8—H8A109.9
O1—Ni1—N288.59 (8)N1—C8—H8B109.9
N1—Ni1—N282.63 (9)C9—C8—H8B109.9
N1i—Ni1—N297.37 (9)H8A—C8—H8B108.3
N2i—Ni1—N2180.0C10—C9—C8115.1 (3)
C2—O1—Ni1125.81 (17)C10—C9—H9A108.5
C3—O2—C12116.9 (2)C8—C9—H9A108.5
C7—N1—C8117.4 (2)C10—C9—H9B108.5
C7—N1—Ni1125.5 (2)C8—C9—H9B108.5
C8—N1—Ni1116.60 (19)H9A—C9—H9B107.5
C11—N2—C10110.2 (2)N2—C10—C9113.2 (2)
C11—N2—Ni1116.00 (19)N2—C10—H10A108.9
C10—N2—Ni1114.88 (18)C9—C10—H10A108.9
C11—N2—H2108.1 (16)N2—C10—H10B108.9
C10—N2—H2107.6 (16)C9—C10—H10B108.9
Ni1—N2—H298.9 (17)H10A—C10—H10B107.7
C6—C1—C2121.0 (3)N2—C11—H11A109.5
C6—C1—C7117.3 (3)N2—C11—H11B109.5
C2—C1—C7121.3 (3)H11A—C11—H11B109.5
O1—C2—C1124.3 (2)N2—C11—H11C109.5
O1—C2—C3120.0 (3)H11A—C11—H11C109.5
C1—C2—C3115.6 (2)H11B—C11—H11C109.5
C4—C3—O2124.0 (3)O2—C12—H12A109.5
C4—C3—C2122.0 (3)O2—C12—H12B109.5
O2—C3—C2114.0 (2)H12A—C12—H12B109.5
C3—C4—C5120.8 (3)O2—C12—H12C109.5
C3—C4—H4119.6H12A—C12—H12C109.5
C5—C4—H4119.6H12B—C12—H12C109.5
C6—C5—C4119.7 (3)
Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Ni(C12H17N2O2)2]
Mr501.26
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)8.762 (3), 15.297 (5), 17.247 (5)
V3)2311.5 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.88
Crystal size (mm)0.23 × 0.21 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.824, 0.858
No. of measured, independent and
observed [I > 2σ(I)] reflections
11114, 2150, 1361
Rint0.058
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.095, 1.02
No. of reflections2150
No. of parameters157
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.33

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

 

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