Redetermination of aqua­(dihydrogen ethyl­enediamine­tetra­acetato-κ5O,O′,N,N′,O′′)nickel(II)

Kočanová, I.; Kuchár, J.; Dankovičová, V.; Černák, J.

doi:10.1107/S1600536810002011

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages m196-m197

https://doi.org/10.1107/S1600536810002011

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Redetermination of aqua(dihydrogen ethylenediaminetetraacetato-κ⁵O,O′,N,N′,O′′)nickel(II)

Ivana Kočanová,^a Juraj Kuchár,^a ^* Vladimíra Dankovičová ^a and Juraj Černák ^a

^aDepartment of Inorganic Chemistry, Institute of Chemistry, P. J.Šafárik University, Moyzesova 11, 041 54 Košice, Slovakia
^*Correspondence e-mail: juraj.kuchar@upjs.sk

(Received 8 January 2010; accepted 15 January 2010; online 23 January 2010)

The crystal structure of the title compound, [Ni(C₁₀H₁₄N₂O₈)(H₂O)] or [Ni(H₂edta)(H₂O)] (H₄edta is ethylenediaminetetraacetic acid), originally determined by Smith & Hoard [J. Am. Chem. Soc. (1959), 81, 556–561] has been redetermined to a significantly higher precision. The Ni^II atom is coordinated in a distorted octahedral geometry by two N atoms and three O atoms from three carboxylate groups of the H₂edta²⁻ ligand and by an O atom of a water molecule. The complex molecules are linked by intermolecular O—H⋯O hydrogen bonds into layers perpendicular to [100].

Related literature

For the crystal structures of nickel(II) complexes with deprotonized derivates of H₄edta, see: Agre, Trunov et al. (1980 ); Agre, Sysoeva et al. (1980 ); Agre et al. (1981 ); Coronado et al. (1986 ); Sysoeva et al. (1981 ); Porai-Koshits et al. (1975 ); Sysoeva et al. (1986 ); Zubkowski et al. (1995 ); Stephens (1969 ). For the earlier determination of the title compound, see: Smith & Hoard (1959 ).

Experimental

Crystal data

[Ni(C₁₀H₁₄N₂O₈)(H₂O)]
M_r = 366.96
Monoclinic, P 2₁ /c
a = 11.6786 (2) Å
b = 6.9358 (1) Å
c = 16.6343 (2) Å
β = 91.140 (1)°
V = 1347.12 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.49 mm⁻¹
T = 291 K
0.35 × 0.31 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 detector
Absorption correction: numerical [Clark & Reid (1995 ) in CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ )] T_min = 0.690, T_max = 0.830
43864 measured reflections
2935 independent reflections
2534 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.055
S = 1.06
2935 reflections
198 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O7ⁱ	0.82	1.77	2.5557 (14)	159
O3—H3⋯O5ⁱⁱ	0.82	1.79	2.5864 (13)	164
O6—H6A⋯O9ⁱⁱⁱ	0.88	2.15	2.9294 (12)	148
O6—H6B⋯O2^iv	0.86	1.81	2.6394 (11)	162
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Crystal Impact, 2007 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536810002011/rz2407sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002011/rz2407Isup2.hkl

checkCIF report

Comment top

We are interested in the synthesis and characterization of Cu—Ni heterobimetallic complexes as models of magnetic alternate chains. Few Cu—Ni heterobimetallic complexes based on edta-type ligands (H₄edta = ethylenediaminetetraacetic acid) have been already structurally characterized (Agre, Trunov et al., 1980; Agre, Sysoeva et al., 1980; Agre et al., 1981). Previously, the crystal structures of one-dimensional [Ni(H₂O)₄(edta)Ni].2H₂O (Coronado et al., 1986), dinuclear [Ni₂(en)(edta)(H₂O)₃].H₂O (Sysoeva et al., 1981), ionic [Ni(H₂O)₆][Ni(Hedta)]₂.2H₂O (Porai-Koshits et al., 1975) and ionic [Ni(en)₃][Ni(edta)].4H₂O (Sysoeva et al., 1986) complexes with the edta(4-) ligand were reported. As a part of our synthetic experiments on Cu—Ni heterobimetallic complexes from the aqueous system Ni²⁺-H₄edta we have isolated the title compound. Its crystal structure was already studied by Smith & Hoard (1959). They obtained a correct structural model, however only two common isotropic thermal parameters were used and the positions of the hydrogen atoms were not determined. Consequently, the precision of the geometric parameters was limited.

In the crystal structure of the title compound (Fig. 1) the nickel(II) atom exhibits an elongated octahedral coordination geometry. Five coordinations sites are occupied by the partially deprotonized, pentadentate chelate H₂edta^2- ligand, which coordinates through both nitrogen atoms and three oxygen atoms from carboxylate groups, among these two are deprotonized. The sixth coordination site is occupied by the oxygen atom of a water molecule. The fourth carboxylate group is not coordinated to the metal. The same type of coordination provided by the H₂edta^2- ligand was observed e.g. in analogous complexes [Co(H₂edta)(H₂O)].H₂O (Zubkowski et al., 1995) and [Cu(H₂edta)(H₂O)] (Stephens, 1969). As expected, the intrachelate angles D1—Ni—D2 (D's are N and O donor atoms) in the title compound are significantly smaller then the ideal value of 90°. In the crystal packing, the H atoms of the water molecule and of two carboxylic groups are involved in intermolecular O—H···O hydrogen bonds (Fig. 2; Table 1) forming layers perpendicular to [100] (Fig. 3).

Related literature top

For the crystal structures of nickel(II) complexes with deprotonized derivates of H₄edta, see: Agre, Trunov et al. (1980); Agre, Sysoeva et al. (1980); Agre et al. (1981); Coronado et al. (1986); Sysoeva et al. (1981); Porai-Koshits et al. (1975); Sysoeva et al. (1986); Zubkowski et al. (1995); Stephens (1969). For the earlier determination of the title compound, see: Smith & Hoard (1959).

Experimental top

Chemicals of reagent grade quality were obtained from commercial sources and were used as received. Solid NiCO₃.2Ni(OH)₂ (0.304 g, 1 mmol), ethylenediaminetetraacetic acid (0.877 g, 3 mmol) and tetraethylammonium bromide (0.421 g, 2 mmol) were dissolved under stirring in 10 cm³ of water at room temperature. The formed blue solution was filtered and left aside for crystallization at room temperature. After eight months, few blue prismatic crystals of the title compound appeared along with white microcrystalline material on slow evaporation of the solvent.

Structure description top

For the crystal structures of nickel(II) complexes with deprotonized derivates of H₄edta, see: Agre, Trunov et al. (1980); Agre, Sysoeva et al. (1980); Agre et al. (1981); Coronado et al. (1986); Sysoeva et al. (1981); Porai-Koshits et al. (1975); Sysoeva et al. (1986); Zubkowski et al. (1995); Stephens (1969). For the earlier determination of the title compound, see: Smith & Hoard (1959).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Crystal Impact, 2007); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. View of the hydrogen bonding network in the title compound. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity. Symmetry codes: (i) 1 - x,1 - y,1 - z; (ii) x,-0.5 - y,1/2 + z; (iii) 1 - x,-y,1 - z; (iv) 1 - x,-1/2 + y,1.5 - z
	Fig. 3. Hydrogen bonded layers in the crystal structure of the title compound. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity.

aqua(dihydrogen ethylenediaminetetraacetato- κ⁵O,O',N,N',O'')nickel(II) top

Crystal data top

[Ni(C₁₀H₁₄N₂O₈)(H₂O)]	F(000) = 760
M_r = 366.96	D_x = 1.809 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 23028 reflections
a = 11.6786 (2) Å	θ = 2.9–29.7°
b = 6.9358 (1) Å	µ = 1.49 mm⁻¹
c = 16.6343 (2) Å	T = 291 K
β = 91.140 (1)°	Prism, blue
V = 1347.12 (3) Å³	0.35 × 0.31 × 0.15 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	2935 independent reflections
Radiation source: fine-focus sealed tube	2534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 8.3438 pixels mm^-1	θ_max = 27.0°, θ_min = 3.0°
ω scans	h = −14→14
Absorption correction: numerical [Clark & Reid (1995) in CrysAlis PRO (Oxford Diffraction, 2009)]	k = −8→8
T_min = 0.690, T_max = 0.830	l = −21→21
43864 measured reflections

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.055	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0343P)² + 0.1019P] where P = (F_o² + 2F_c²)/3
2935 reflections	(Δ/σ)_max < 0.001
198 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

[Ni(C₁₀H₁₄N₂O₈)(H₂O)]	V = 1347.12 (3) Å³
M_r = 366.96	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6786 (2) Å	µ = 1.49 mm⁻¹
b = 6.9358 (1) Å	T = 291 K
c = 16.6343 (2) Å	0.35 × 0.31 × 0.15 mm
β = 91.140 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	2935 independent reflections
Absorption correction: numerical [Clark & Reid (1995) in CrysAlis PRO (Oxford Diffraction, 2009)]	2534 reflections with I > 2σ(I)
T_min = 0.690, T_max = 0.830	R_int = 0.030
43864 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.055	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
2935 reflections	Δρ_min = −0.18 e Å⁻³
198 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	0.328740 (14)	0.17883 (3)	0.575762 (10)	0.01636 (7)
C1	0.31560 (12)	0.2378 (2)	0.75097 (8)	0.0200 (3)
H1A	0.3556	0.1440	0.7845	0.024*
H1B	0.2635	0.3081	0.7850	0.024*
C2	0.40253 (12)	0.3781 (2)	0.71795 (9)	0.0228 (3)
C3	0.13224 (12)	0.2211 (2)	0.67502 (9)	0.0201 (3)
H3A	0.0979	0.2483	0.7264	0.024*
H3B	0.0831	0.1308	0.6462	0.024*
C4	0.14153 (12)	0.4066 (2)	0.62701 (8)	0.0199 (3)
H4A	0.0659	0.4615	0.6182	0.024*
H4B	0.1878	0.4994	0.6568	0.024*
C5	0.11558 (13)	0.2632 (2)	0.49152 (9)	0.0214 (3)
H5A	0.1084	0.3382	0.4425	0.026*
H5B	0.0404	0.2557	0.5150	0.026*
C6	0.15460 (13)	0.0613 (2)	0.47048 (9)	0.0235 (3)
C7	0.24547 (12)	0.5370 (2)	0.51157 (9)	0.0201 (3)
H7A	0.2688	0.6278	0.5531	0.024*
H7B	0.1889	0.5995	0.4769	0.024*
C8	0.34815 (11)	0.4803 (2)	0.46292 (8)	0.0190 (3)
C9	0.24045 (13)	−0.0747 (2)	0.70537 (9)	0.0226 (3)
H9A	0.3177	−0.1259	0.7083	0.027*
H9B	0.2015	−0.1366	0.6603	0.027*
C10	0.17986 (12)	−0.1308 (2)	0.78149 (8)	0.0205 (3)
N1	0.24747 (9)	0.13322 (17)	0.68850 (7)	0.0161 (2)
N2	0.19470 (10)	0.36547 (16)	0.54870 (7)	0.0155 (2)
O1	0.37976 (9)	0.61360 (17)	0.41363 (7)	0.0304 (3)
H1	0.4430	0.5870	0.3962	0.046*
O2	0.45601 (11)	0.4832 (2)	0.76438 (7)	0.0434 (3)
O3	0.18039 (11)	−0.31910 (15)	0.79037 (7)	0.0333 (3)
H3	0.1531	−0.3471	0.8339	0.050*
O4	0.13713 (9)	−0.01849 (16)	0.82733 (6)	0.0293 (3)
O5	0.09695 (7)	−0.02364 (13)	0.41745 (5)	0.0374 (3)
O6	0.45974 (7)	−0.01221 (13)	0.58721 (5)	0.0402 (3)
H6A	0.4811	−0.1050	0.5547	0.060*
H6B	0.4970	−0.0318	0.6315	0.060*
O7	0.41759 (8)	0.37646 (16)	0.64146 (6)	0.0234 (2)
O8	0.23968 (9)	−0.00858 (15)	0.50781 (6)	0.0280 (2)
O9	0.39642 (9)	0.32508 (15)	0.47244 (6)	0.0232 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01745 (10)	0.01728 (10)	0.01441 (10)	0.00186 (7)	0.00174 (6)	−0.00042 (7)
C1	0.0201 (7)	0.0249 (8)	0.0149 (7)	−0.0024 (6)	−0.0003 (5)	−0.0006 (6)
C2	0.0189 (7)	0.0290 (8)	0.0205 (7)	−0.0038 (6)	−0.0002 (6)	−0.0009 (6)
C3	0.0146 (6)	0.0271 (8)	0.0187 (7)	−0.0010 (6)	0.0028 (5)	0.0029 (6)
C4	0.0194 (7)	0.0231 (8)	0.0172 (7)	0.0046 (6)	0.0031 (5)	−0.0012 (6)
C5	0.0212 (7)	0.0236 (8)	0.0190 (7)	−0.0046 (6)	−0.0042 (6)	0.0006 (6)
C6	0.0257 (8)	0.0259 (8)	0.0191 (7)	−0.0088 (6)	0.0063 (6)	−0.0056 (6)
C7	0.0218 (7)	0.0150 (7)	0.0236 (7)	−0.0007 (6)	0.0033 (6)	0.0014 (6)
C8	0.0179 (7)	0.0226 (8)	0.0165 (7)	−0.0058 (6)	−0.0020 (5)	0.0006 (6)
C9	0.0312 (8)	0.0165 (8)	0.0203 (7)	−0.0005 (6)	0.0067 (6)	0.0000 (6)
C10	0.0228 (7)	0.0214 (8)	0.0172 (7)	−0.0028 (6)	−0.0009 (6)	0.0000 (6)
N1	0.0177 (6)	0.0157 (6)	0.0151 (6)	−0.0010 (4)	0.0018 (4)	−0.0003 (5)
N2	0.0170 (5)	0.0144 (6)	0.0150 (5)	−0.0014 (4)	0.0010 (4)	−0.0014 (4)
O1	0.0223 (5)	0.0333 (6)	0.0359 (6)	−0.0026 (5)	0.0076 (5)	0.0145 (5)
O2	0.0451 (7)	0.0591 (9)	0.0260 (6)	−0.0309 (7)	−0.0008 (5)	−0.0090 (6)
O3	0.0559 (8)	0.0203 (6)	0.0240 (6)	−0.0024 (5)	0.0132 (5)	0.0044 (5)
O4	0.0390 (6)	0.0272 (6)	0.0222 (5)	0.0020 (5)	0.0111 (5)	−0.0003 (5)
O5	0.0315 (6)	0.0481 (8)	0.0327 (6)	−0.0110 (6)	0.0007 (5)	−0.0250 (6)
O6	0.0448 (7)	0.0493 (8)	0.0263 (6)	0.0301 (6)	−0.0022 (5)	−0.0052 (6)
O7	0.0203 (5)	0.0324 (6)	0.0176 (5)	−0.0079 (4)	0.0021 (4)	−0.0005 (4)
O8	0.0352 (6)	0.0183 (5)	0.0304 (6)	0.0005 (5)	−0.0026 (5)	−0.0066 (5)
O9	0.0245 (5)	0.0244 (6)	0.0210 (5)	0.0030 (4)	0.0060 (4)	0.0019 (4)

Geometric parameters (Å, º) top

Ni1—O8	2.0006 (10)	C5—H5A	0.9700
Ni1—O7	2.0260 (10)	C5—H5B	0.9700
Ni1—O6	2.0300 (9)	C6—O5	1.2468 (16)
Ni1—N2	2.0738 (11)	C6—O8	1.2582 (19)
Ni1—N1	2.1421 (11)	C7—N2	1.4708 (17)
Ni1—O9	2.1591 (10)	C7—C8	1.5121 (19)
C1—N1	1.4852 (18)	C7—H7A	0.9700
C1—C2	1.517 (2)	C7—H7B	0.9700
C1—H1A	0.9700	C8—O9	1.2239 (17)
C1—H1B	0.9700	C8—O1	1.2945 (17)
C2—O2	1.2245 (18)	C9—N1	1.4717 (18)
C2—O7	1.2880 (17)	C9—C10	1.514 (2)
C3—N1	1.4903 (18)	C9—H9A	0.9700
C3—C4	1.519 (2)	C9—H9B	0.9700
C3—H3A	0.9700	C10—O4	1.2054 (17)
C3—H3B	0.9700	C10—O3	1.3140 (18)
C4—N2	1.4818 (17)	O1—H1	0.8200
C4—H4A	0.9700	O3—H3	0.8200
C4—H4B	0.9700	O6—H6A	0.880
C5—N2	1.4922 (17)	O6—H6B	0.859
C5—C6	1.516 (2)

O8—Ni1—O7	177.83 (4)	O5—C6—O8	125.26 (14)
O8—Ni1—O6	90.65 (4)	O5—C6—C5	116.05 (13)
O7—Ni1—O6	90.80 (4)	O8—C6—C5	118.68 (13)
O8—Ni1—N2	84.33 (4)	N2—C7—C8	110.17 (11)
O7—Ni1—N2	94.08 (4)	N2—C7—H7A	109.6
O6—Ni1—N2	172.75 (4)	C8—C7—H7A	109.6
O8—Ni1—N1	99.45 (4)	N2—C7—H7B	109.6
O7—Ni1—N1	81.88 (4)	C8—C7—H7B	109.6
O6—Ni1—N1	99.65 (4)	H7A—C7—H7B	108.1
N2—Ni1—N1	86.36 (4)	O9—C8—O1	125.02 (13)
O8—Ni1—O9	92.86 (4)	O9—C8—C7	121.86 (13)
O7—Ni1—O9	85.40 (4)	O1—C8—C7	113.09 (13)
O6—Ni1—O9	95.41 (4)	N1—C9—C10	116.13 (12)
N2—Ni1—O9	79.67 (4)	N1—C9—H9A	108.3
N1—Ni1—O9	160.37 (4)	C10—C9—H9A	108.3
N1—C1—C2	114.38 (11)	N1—C9—H9B	108.3
N1—C1—H1A	108.7	C10—C9—H9B	108.3
C2—C1—H1A	108.7	H9A—C9—H9B	107.4
N1—C1—H1B	108.7	O4—C10—O3	124.91 (14)
C2—C1—H1B	108.7	O4—C10—C9	124.69 (13)
H1A—C1—H1B	107.6	O3—C10—C9	110.40 (12)
O2—C2—O7	123.39 (14)	C9—N1—C1	112.09 (11)
O2—C2—C1	119.36 (13)	C9—N1—C3	112.08 (11)
O7—C2—C1	117.23 (13)	C1—N1—C3	112.03 (11)
N1—C3—C4	110.60 (11)	C9—N1—Ni1	109.82 (8)
N1—C3—H3A	109.5	C1—N1—Ni1	107.45 (8)
C4—C3—H3A	109.5	C3—N1—Ni1	102.85 (8)
N1—C3—H3B	109.5	C7—N2—C4	113.14 (11)
C4—C3—H3B	109.5	C7—N2—C5	111.51 (11)
H3A—C3—H3B	108.1	C4—N2—C5	112.76 (11)
N2—C4—C3	109.56 (12)	C7—N2—Ni1	106.69 (8)
N2—C4—H4A	109.8	C4—N2—Ni1	104.89 (8)
C3—C4—H4A	109.8	C5—N2—Ni1	107.26 (8)
N2—C4—H4B	109.8	C8—O1—H1	109.5
C3—C4—H4B	109.8	C10—O3—H3	109.5
H4A—C4—H4B	108.2	Ni1—O6—H6A	129.9
N2—C5—C6	113.66 (12)	Ni1—O6—H6B	123.5
N2—C5—H5A	108.8	H6A—O6—H6B	105.4
C6—C5—H5A	108.8	C2—O7—Ni1	117.40 (9)
N2—C5—H5B	108.8	C6—O8—Ni1	115.17 (10)
C6—C5—H5B	108.8	C8—O9—Ni1	109.95 (9)
H5A—C5—H5B	107.7

N1—C1—C2—O2	173.79 (14)	C3—C4—N2—C5	73.50 (14)
N1—C1—C2—O7	−7.7 (2)	C3—C4—N2—Ni1	−42.89 (12)
N1—C3—C4—N2	58.79 (15)	C6—C5—N2—C7	116.31 (13)
N2—C5—C6—O5	−173.79 (12)	C6—C5—N2—C4	−115.13 (13)
N2—C5—C6—O8	7.39 (19)	C6—C5—N2—Ni1	−0.16 (13)
N2—C7—C8—O9	−17.75 (18)	O8—Ni1—N2—C7	−123.50 (9)
N2—C7—C8—O1	164.25 (12)	O7—Ni1—N2—C7	55.03 (9)
N1—C9—C10—O4	0.8 (2)	N1—Ni1—N2—C7	136.61 (9)
N1—C9—C10—O3	−179.23 (13)	O9—Ni1—N2—C7	−29.54 (8)
C10—C9—N1—C1	63.40 (16)	O8—Ni1—N2—C4	116.22 (9)
C10—C9—N1—C3	−63.58 (16)	O7—Ni1—N2—C4	−65.25 (9)
C10—C9—N1—Ni1	−177.24 (10)	N1—Ni1—N2—C4	16.33 (9)
C2—C1—N1—C9	133.66 (13)	O9—Ni1—N2—C4	−149.82 (9)
C2—C1—N1—C3	−99.34 (14)	O8—Ni1—N2—C5	−3.90 (8)
C2—C1—N1—Ni1	12.92 (14)	O7—Ni1—N2—C5	174.63 (8)
C4—C3—N1—C9	−157.70 (11)	N1—Ni1—N2—C5	−103.78 (9)
C4—C3—N1—C1	75.29 (14)	O9—Ni1—N2—C5	90.06 (9)
C4—C3—N1—Ni1	−39.81 (12)	O2—C2—O7—Ni1	175.79 (13)
O8—Ni1—N1—C9	48.50 (10)	C1—C2—O7—Ni1	−2.69 (18)
O7—Ni1—N1—C9	−133.23 (10)	O6—Ni1—O7—C2	−91.55 (10)
O6—Ni1—N1—C9	−43.79 (9)	N2—Ni1—O7—C2	93.81 (11)
N2—Ni1—N1—C9	132.13 (10)	N1—Ni1—O7—C2	8.08 (11)
O9—Ni1—N1—C9	176.63 (11)	O9—Ni1—O7—C2	173.09 (11)
O8—Ni1—N1—C1	170.66 (9)	O5—C6—O8—Ni1	170.31 (11)
O7—Ni1—N1—C1	−11.06 (9)	C5—C6—O8—Ni1	−10.99 (17)
O6—Ni1—N1—C1	78.38 (8)	O6—Ni1—O8—C6	−166.26 (10)
N2—Ni1—N1—C1	−105.71 (9)	N2—Ni1—O8—C6	8.50 (10)
O9—Ni1—N1—C1	−61.20 (17)	N1—Ni1—O8—C6	93.84 (11)
O8—Ni1—N1—C3	−70.97 (9)	O9—Ni1—O8—C6	−70.82 (11)
O7—Ni1—N1—C3	107.30 (9)	O1—C8—O9—Ni1	169.74 (12)
O6—Ni1—N1—C3	−163.26 (8)	C7—C8—O9—Ni1	−8.00 (16)
N2—Ni1—N1—C3	12.65 (8)	O8—Ni1—O9—C8	105.34 (9)
O9—Ni1—N1—C3	57.16 (16)	O7—Ni1—O9—C8	−73.36 (9)
C8—C7—N2—C4	148.46 (11)	O6—Ni1—O9—C8	−163.74 (9)
C8—C7—N2—C5	−83.18 (14)	N2—Ni1—O9—C8	21.64 (9)
C8—C7—N2—Ni1	33.64 (12)	N1—Ni1—O9—C8	−23.69 (18)
C3—C4—N2—C7	−158.79 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7ⁱ	0.82	1.77	2.5557 (14)	159
O3—H3···O5ⁱⁱ	0.82	1.79	2.5864 (13)	164
O6—H6A···O9ⁱⁱⁱ	0.88	2.15	2.9294 (12)	148
O6—H6B···O2^iv	0.86	1.81	2.6394 (11)	162

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₁₄N₂O₈)(H₂O)]
M_r	366.96
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	11.6786 (2), 6.9358 (1), 16.6343 (2)
β (°)	91.140 (1)
V (Å³)	1347.12 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.49
Crystal size (mm)	0.35 × 0.31 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector
Absorption correction	Numerical [Clark & Reid (1995) in CrysAlis PRO (Oxford Diffraction, 2009)]
T_min, T_max	0.690, 0.830
No. of measured, independent and observed [I > 2σ(I)] reflections	43864, 2935, 2534
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.055, 1.06
No. of reflections	2935
No. of parameters	198
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Crystal Impact, 2007).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7ⁱ	0.82	1.77	2.5557 (14)	159
O3—H3···O5ⁱⁱ	0.82	1.79	2.5864 (13)	164
O6—H6A···O9ⁱⁱⁱ	0.88	2.15	2.9294 (12)	148
O6—H6B···O2^iv	0.86	1.81	2.6394 (11)	162

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

Acknowledgements

This work was supported by the Slovak grant agency APVV (contract Nos. APVV-VVCE-0058–07 and APVV-0006–07) and the grant agency VEGA (grant No. 1/0089/09). Support from P. J. Šafárik University (VVGS 37/09–10) is also gratefully acknowledged.

References

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