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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055092/pk2060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055092/pk2060Isup2.hkl
Contains datablock I

CCDC reference: 672615

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.108
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O3 .. 6.13 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3 PLAT480_ALERT_4_C Long H...A H-Bond Reported H7D .. O5 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7E .. N3 .. 2.64 Ang.
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 2.08 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

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)2·2H2OF(000) = 1544
Mr = 727.39Dx = 1.399 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5968 reflections
a = 14.101 (4) Åθ = 2.4–25.2°
b = 10.369 (3) ŵ = 0.63 mm1
c = 23.627 (6) ÅT = 298 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)
Graphite monochromatorRint = 0.040
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1818
Tmin = 0.833, Tmax = 0.868k = 1313
27825 measured reflectionsl = 3030
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0472P)2 + 1.9738P]
where P = (Fo2 + 2Fc2)/3
3967 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.51 e Å3
6 restraintsΔρmin = 0.36 e Å3
Crystal data top
[Ni(C13H20N2O2)2(H2O)2](NO3)2·2H2OV = 3454.7 (17) Å3
Mr = 727.39Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 14.101 (4) ŵ = 0.63 mm1
b = 10.369 (3) ÅT = 298 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 Å3
3967 reflectionsΔρmin = 0.36 e Å3
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)
H40.64060.17680.38390.055*
C50.62353 (16)0.0365 (3)0.44243 (11)0.0527 (6)
H50.55760.03830.44290.063*
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)
H7A0.74630.33990.36080.088*
H7B0.83170.33570.31840.088*
H7C0.74350.24620.30880.088*
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)
H13A1.01140.10660.70800.113*
H13B1.07040.03740.75530.113*
H13C1.10450.03220.69220.113*
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, º) 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 code: (i) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) 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)1.97 (2)2.765 (2)157 (3)
O3—H3B···O5iii0.85 (3)2.12 (2)2.859 (3)146 (2)
O7—H7D···O40.85 (3)1.94 (1)2.765 (3)166 (3)
O7—H7D···N30.85 (3)2.59 (2)3.300 (3)143 (3)
O7—H7D···O50.85 (3)2.65 (2)3.175 (3)121 (2)
O7—H7E···O6iv0.84 (3)2.04 (1)2.875 (3)172 (3)
O7—H7E···O4iv0.84 (3)2.55 (2)3.202 (3)135 (3)
O7—H7E···N3iv0.84 (3)2.64 (1)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, y1/2, z.

Experimental details

Crystal data
Chemical formula[Ni(C13H20N2O2)2(H2O)2](NO3)2·2H2O
Mr727.39
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)14.101 (4), 10.369 (3), 23.627 (6)
V3)3454.7 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.63
Crystal size (mm)0.30 × 0.27 × 0.23
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.833, 0.868
No. of measured, independent and
observed [I > 2σ(I)] reflections
27825, 3967, 3000
Rint0.040
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.108, 1.02
No. of reflections3967
No. of parameters229
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.51, 0.36

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.901.782.631 (2)157.5
N2—H2A···O2i0.902.463.086 (2)127.4
N2—H2B···O7ii0.902.032.907 (3)165.5
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, y1/2, z.
 

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