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Acta Cryst. (2007). E63, m2945-m2946    [ doi:10.1107/S1600536807055092 ]

Diaquabis{2-[2-(isopropylammonio)ethyliminomethyl]-6-methoxyphenolato}nickel(II) dinitrate dihydrate

Y.-Z. Wang, L.-L. Li, Y.-Q. Su and C. Li

Abstract top

The title compound, [Ni(C13H20N2O2)2(H2O)2](NO3)2·2H2O, consists of a mononuclear nickel(II) complex, two nitrate anions and two solvent water molecules. The Ni atom lies on an inversion centre and is chelated by the phenolic O and imine N atoms from two Schiff base ligands, and coordinated by the O atoms from two water molecules, giving a slightly distorted octahedral geometry. Within the crystal structure, the components form chains parallel to the a axis by intermolecular N-H...O, O-H...O and O-H...N hydrogen bonds.

Comment top

Schiff base nickel complexes have been received much attention in coordination chemistry (Di Bella et al., 1994; Lacroix et al., 1996; Averseng et al., 1999; Wang, 2005; Fun et al., 2001; Zhang et al., 2005). Recently, we have reported the structure of a Schiff base nickel(II) complex (Su et al., 2006). As a further investigation of the structures of such complexes, the title compound is reported here.

The complex consists of a mononuclear nickel(II) complex, with two nitrate anions and two lattice water molecules, as shown in Fig. 1. The Ni atom, lies on an inversion centre; it is chelated by the phenolic O and imine N atoms from two Schiff base ligands, and is coordinated by the O atoms from two water molecules, giving a slightly distorted octahedral geometry. The three trans angles at Ni are 180° by symmetry, the other angles are close to 90°, varying from 87.25 (6) to 92.75 (6)°. The Ni—O and Ni—N bond lengths are normal and comparable to those observed in other similar nickel(II) complexes (Wei, 2005; Ali et al., 2004; Sarı et al., 2006; Gomes et al., 2000).

In the crystal structure, molecules form chains running parallel to the a axis through intermolecular N—H···O, O—H···O and O—H···N hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For related literature, see: Ali et al. (2004); Averseng et al. (1999); Di Bella et al. (1994); Fun et al. (2001); Gomes et al. (2000); Lacroix et al. (1996); Sarı et al. (2006); Su et al. (2006); Wang (2005); Wei (2005); Zhang et al. (2005).

Experimental top

3-Methoxysalicylaldehyde (1.0 mmol, 152.0 mg), N-isopropylethane-1,2-diamine (1.0 mmol, 102.2 mg), and Ni(NO3)2·6H2O (0.5 mmol, 145.3 mg) were dissolved in a 95% ethanol solution (30 ml). The mixture was stirred at room temperature for about 1 h to give a green solution. After keeping the solution in air for 12 days, green block-like crystals were formed.

Refinement top

Water H atoms were located in a difference Fourier map and refined isotropically, with O—H and H···H distances restrained to 0.85 (1) Å and 1.37 (2) Å respectively. The other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms are at the symmetry related position (2 − x, −y, 1 − z).
[Figure 2] Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.
Diaquabis{2-[2-(isopropylammonio)ethyliminomethyl]-6-methoxyphenolato}nickel(II) dinitrate dihydrate top
Crystal data top
[Ni(C13H20N2O2)2(H2O)2](NO3)2·2H2OF000 = 1544
Mr = 727.39Dx = 1.399 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5968 reflections
a = 14.101 (4) Åθ = 2.4–25.2º
b = 10.369 (3) ŵ = 0.63 mm−1
c = 23.627 (6) ÅT = 298 (2) K
V = 3454.7 (17) Å3Block, green
Z = 40.30 × 0.27 × 0.23 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3967 independent reflections
Radiation source: fine-focus sealed tube3000 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
T = 298(2) Kθmax = 27.5º
ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −18→18
Tmin = 0.833, Tmax = 0.868k = −13→13
27825 measured reflectionsl = −30→30
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.108  w = 1/[σ2(Fo2) + (0.0472P)2 + 1.9738P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3967 reflectionsΔρmax = 0.51 e Å−3
229 parametersΔρmin = −0.36 e Å−3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ni(C13H20N2O2)2(H2O)2](NO3)2·2H2OV = 3454.7 (17) Å3
Mr = 727.39Z = 4
Orthorhombic, PbcaMo Kα
a = 14.101 (4) ŵ = 0.63 mm−1
b = 10.369 (3) ÅT = 298 (2) K
c = 23.627 (6) Å0.30 × 0.27 × 0.23 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3967 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		3000 reflections with I > 2σ(I)
Tmin = 0.833, Tmax = 0.868Rint = 0.040
27825 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0406 restraints
wR(F2) = 0.108H atoms treated by a mixture of
independent and constrained refinement
S = 1.02Δρmax = 0.51 e Å−3
3967 reflectionsΔρmin = −0.36 e Å−3
229 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 > 2σ(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
Ni11.00000.00000.50000.02925 (11)
O10.91529 (9)−0.02221 (14)0.43343 (6)0.0370 (3)
O20.82723 (11)−0.18753 (15)0.36977 (7)0.0468 (4)
O31.07598 (11)0.14933 (15)0.45794 (7)0.0446 (4)
O40.18849 (17)0.3220 (2)0.33180 (15)0.1183 (11)
O50.04457 (13)0.29566 (19)0.35709 (9)0.0711 (6)
O60.11196 (19)0.4802 (2)0.36353 (12)0.0932 (8)
O70.19608 (13)0.07169 (17)0.37196 (9)0.0592 (5)
N10.90533 (12)0.13969 (15)0.52859 (7)0.0324 (4)
N20.96617 (12)0.09622 (16)0.64619 (7)0.0355 (4)
H2A1.01800.07960.62520.043*
H2B0.92350.03380.63890.043*
N30.11452 (15)0.3664 (2)0.35155 (9)0.0530 (5)
C10.77137 (14)0.0516 (2)0.47669 (9)0.0354 (4)
C20.82259 (14)−0.02761 (19)0.43900 (8)0.0320 (4)
C30.77055 (14)−0.1139 (2)0.40424 (9)0.0368 (5)
C40.67340 (16)−0.1185 (2)0.40649 (10)0.0458 (5)
H40.6406−0.17680.38390.055*
C50.62353 (16)−0.0365 (3)0.44243 (11)0.0527 (6)
H50.5576−0.03830.44290.063*
C60.67153 (15)0.0466 (3)0.47693 (10)0.0466 (5)
H60.63780.10080.50100.056*
C70.7837 (2)−0.2852 (2)0.33677 (11)0.0584 (7)
H7A0.7463−0.33990.36080.088*
H7B0.8317−0.33570.31840.088*
H7C0.7435−0.24620.30880.088*
C80.81822 (15)0.1435 (2)0.51351 (9)0.0372 (5)
H80.78180.21120.52740.045*
C90.93993 (15)0.24570 (19)0.56478 (9)0.0390 (5)
H9A0.90730.32450.55430.047*
H9B1.00700.25840.55760.047*
C100.92553 (16)0.2217 (2)0.62739 (9)0.0422 (5)
H10A0.95500.29100.64870.051*
H10B0.85820.22290.63570.051*
C110.99340 (16)0.0882 (2)0.70763 (9)0.0445 (5)
H111.03430.16200.71630.053*
C120.9065 (2)0.0974 (4)0.74436 (11)0.0773 (9)
H12A0.87370.17640.73630.116*
H12B0.92500.09610.78350.116*
H12C0.86550.02570.73670.116*
C131.0501 (3)−0.0329 (3)0.71657 (12)0.0756 (9)
H13A1.0114−0.10660.70800.113*
H13B1.0704−0.03740.75530.113*
H13C1.1045−0.03220.69220.113*
H3A1.1215 (14)0.117 (3)0.4393 (11)0.080*
H3B1.0443 (17)0.195 (3)0.4351 (10)0.080*
H7D0.195 (2)0.1423 (17)0.3541 (12)0.080*
H7E0.2499 (11)0.038 (2)0.3686 (13)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02767 (19)0.02977 (19)0.03031 (19)0.00044 (14)−0.00154 (14)−0.00484 (14)
O10.0275 (7)0.0491 (9)0.0345 (7)0.0027 (6)−0.0017 (6)−0.0104 (6)
O20.0431 (8)0.0485 (9)0.0488 (9)−0.0050 (7)−0.0034 (7)−0.0174 (7)
O30.0473 (9)0.0403 (9)0.0461 (9)−0.0027 (7)0.0043 (7)0.0002 (7)
O40.0653 (14)0.0643 (14)0.225 (3)0.0072 (12)0.0497 (18)0.0195 (18)
O50.0448 (10)0.0706 (13)0.0980 (16)−0.0061 (9)−0.0065 (10)0.0168 (11)
O60.1038 (19)0.0531 (13)0.123 (2)−0.0006 (12)0.0109 (16)−0.0196 (13)
O70.0506 (10)0.0472 (10)0.0798 (13)0.0028 (8)0.0140 (10)0.0007 (9)
N10.0364 (9)0.0298 (8)0.0311 (8)0.0021 (7)−0.0024 (7)−0.0023 (7)
N20.0376 (9)0.0361 (9)0.0329 (9)0.0005 (7)0.0028 (7)−0.0068 (7)
N30.0467 (12)0.0479 (12)0.0643 (13)0.0041 (10)−0.0029 (10)0.0125 (10)
C10.0298 (10)0.0415 (11)0.0350 (10)0.0065 (9)−0.0043 (8)0.0004 (9)
C20.0293 (9)0.0350 (10)0.0318 (10)0.0025 (8)−0.0028 (8)0.0032 (8)
C30.0368 (11)0.0376 (11)0.0361 (11)−0.0016 (9)−0.0045 (8)0.0021 (9)
C40.0385 (12)0.0497 (13)0.0491 (13)−0.0087 (10)−0.0110 (10)0.0021 (11)
C50.0286 (11)0.0681 (16)0.0613 (16)−0.0003 (11)−0.0040 (11)0.0038 (13)
C60.0332 (11)0.0588 (14)0.0479 (13)0.0095 (10)−0.0006 (10)−0.0021 (11)
C70.0668 (17)0.0509 (14)0.0574 (15)−0.0103 (12)−0.0109 (13)−0.0141 (12)
C80.0378 (11)0.0377 (11)0.0361 (11)0.0097 (9)0.0019 (8)−0.0022 (9)
C90.0467 (12)0.0281 (10)0.0422 (11)0.0032 (9)−0.0033 (9)−0.0052 (9)
C100.0475 (12)0.0386 (11)0.0404 (12)0.0082 (10)−0.0002 (10)−0.0109 (9)
C110.0512 (13)0.0503 (13)0.0320 (11)−0.0018 (11)−0.0031 (9)−0.0079 (10)
C120.077 (2)0.118 (3)0.0371 (14)−0.0082 (19)0.0125 (13)−0.0068 (16)
C130.113 (3)0.0651 (18)0.0485 (16)0.0218 (18)−0.0159 (17)0.0013 (13)
Geometric parameters (Å, °) top
Ni1—O1i1.9884 (14)C2—C31.419 (3)
Ni1—O11.9884 (14)C3—C41.372 (3)
Ni1—N12.0824 (16)C4—C51.393 (3)
Ni1—N1i2.0824 (16)C4—H40.9300
Ni1—O32.1291 (16)C5—C61.366 (4)
Ni1—O3i2.1291 (16)C5—H50.9300
O1—C21.315 (2)C6—H60.9300
O2—C31.373 (3)C7—H7A0.9600
O2—C71.418 (3)C7—H7B0.9600
O3—H3A0.85 (3)C7—H7C0.9600
O3—H3B0.85 (3)C8—H80.9300
O4—N31.232 (3)C9—C101.514 (3)
O5—N31.236 (3)C9—H9A0.9700
O6—N31.214 (3)C9—H9B0.9700
O7—H7D0.845 (10)C10—H10A0.9700
O7—H7E0.840 (10)C10—H10B0.9700
N1—C81.279 (3)C11—C121.504 (3)
N1—C91.476 (2)C11—C131.504 (4)
N2—C101.490 (3)C11—H110.9800
N2—C111.504 (3)C12—H12A0.9600
N2—H2A0.9000C12—H12B0.9600
N2—H2B0.9000C12—H12C0.9600
C1—C61.409 (3)C13—H13A0.9600
C1—C21.410 (3)C13—H13B0.9600
C1—C81.450 (3)C13—H13C0.9600
O1i—Ni1—O1180.0C6—C5—C4119.9 (2)
O1i—Ni1—N192.75 (6)C6—C5—H5120.0
O1—Ni1—N187.25 (6)C4—C5—H5120.0
O1i—Ni1—N1i87.25 (6)C5—C6—C1121.1 (2)
O1—Ni1—N1i92.75 (6)C5—C6—H6119.5
N1—Ni1—N1i180.00 (8)C1—C6—H6119.5
O1i—Ni1—O389.01 (6)O2—C7—H7A109.5
O1—Ni1—O390.99 (6)O2—C7—H7B109.5
N1—Ni1—O388.18 (7)H7A—C7—H7B109.5
N1i—Ni1—O391.82 (7)O2—C7—H7C109.5
O1i—Ni1—O3i90.99 (6)H7A—C7—H7C109.5
O1—Ni1—O3i89.01 (6)H7B—C7—H7C109.5
N1—Ni1—O3i91.82 (7)N1—C8—C1125.74 (19)
N1i—Ni1—O3i88.18 (7)N1—C8—H8117.1
O3—Ni1—O3i180.0C1—C8—H8117.1
C2—O1—Ni1121.53 (13)N1—C9—C10113.55 (17)
C3—O2—C7118.10 (18)N1—C9—H9A108.9
Ni1—O3—H3A110 (2)C10—C9—H9A108.9
Ni1—O3—H3B116 (2)N1—C9—H9B108.9
H3A—O3—H3B107 (2)C10—C9—H9B108.9
H7D—O7—H7E109 (2)H9A—C9—H9B107.7
C8—N1—C9117.10 (17)N2—C10—C9112.53 (17)
C8—N1—Ni1123.15 (14)N2—C10—H10A109.1
C9—N1—Ni1119.61 (13)C9—C10—H10A109.1
C10—N2—C11115.72 (16)N2—C10—H10B109.1
C10—N2—H2A108.4C9—C10—H10B109.1
C11—N2—H2A108.4H10A—C10—H10B107.8
C10—N2—H2B108.4N2—C11—C12110.22 (19)
C11—N2—H2B108.4N2—C11—C13108.50 (19)
H2A—N2—H2B107.4C12—C11—C13113.9 (2)
O6—N3—O4118.5 (2)N2—C11—H11108.0
O6—N3—O5121.9 (2)C12—C11—H11108.0
O4—N3—O5119.6 (2)C13—C11—H11108.0
C6—C1—C2119.5 (2)C11—C12—H12A109.5
C6—C1—C8118.5 (2)C11—C12—H12B109.5
C2—C1—C8121.90 (18)H12A—C12—H12B109.5
O1—C2—C1123.19 (18)C11—C12—H12C109.5
O1—C2—C3118.87 (18)H12A—C12—H12C109.5
C1—C2—C3117.90 (18)H12B—C12—H12C109.5
C4—C3—O2125.8 (2)C11—C13—H13A109.5
C4—C3—C2121.0 (2)C11—C13—H13B109.5
O2—C3—C2113.14 (17)H13A—C13—H13B109.5
C3—C4—C5120.5 (2)C11—C13—H13C109.5
C3—C4—H4119.8H13A—C13—H13C109.5
C5—C4—H4119.8H13B—C13—H13C109.5
Symmetry codes: (i) −x+2, −y, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.901.782.631 (2)158
N2—H2A···O2i0.902.463.086 (2)127
N2—H2B···O7ii0.902.032.907 (3)166
O3—H3A···O7iii0.85 (3)1.965 (15)2.765 (2)157 (3)
O3—H3B···O5iii0.85 (3)2.118 (18)2.859 (3)146 (2)
O7—H7D···O40.85 (3)1.939 (12)2.765 (3)166 (3)
O7—H7D···N30.85 (3)2.588 (18)3.300 (3)143 (3)
O7—H7D···O50.85 (3)2.65 (2)3.175 (3)121 (2)
O7—H7E···O6iv0.84 (3)2.041 (11)2.875 (3)172 (3)
O7—H7E···O4iv0.84 (3)2.55 (2)3.202 (3)135 (3)
O7—H7E···N3iv0.84 (3)2.641 (13)3.449 (3)162 (3)
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x+1, y, z; (iv) −x+1/2, y−1/2, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.901.782.631 (2)158
N2—H2A···O2i0.902.463.086 (2)127
N2—H2B···O7ii0.902.032.907 (3)166
O3—H3A···O7iii0.85 (3)1.965 (15)2.765 (2)157 (3)
O3—H3B···O5iii0.85 (3)2.118 (18)2.859 (3)146 (2)
O7—H7D···O40.85 (3)1.939 (12)2.765 (3)166 (3)
O7—H7D···N30.85 (3)2.588 (18)3.300 (3)143 (3)
O7—H7D···O50.85 (3)2.65 (2)3.175 (3)121 (2)
O7—H7E···O6iv0.84 (3)2.041 (11)2.875 (3)172 (3)
O7—H7E···O4iv0.84 (3)2.55 (2)3.202 (3)135 (3)
O7—H7E···N3iv0.84 (3)2.641 (13)3.449 (3)162 (3)
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x+1, y, z; (iv) −x+1/2, y−1/2, z.
references
References top

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