{μ-trans-N,N′-Bis[2-(2-hydroxy­ethyl­amino)eth­yl]oxamidato(2−)}bis­[picrato­nickel(II)]

Tian, C.

doi:10.1107/S1600536809052933

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m71

doi:10.1107/S1600536809052933

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{μ-trans-N,N′-Bis[2-(2-hydroxyethylamino)ethyl]oxamidato(2−)}bis[picratonickel(II)]

Chunliang Tian ^a ^*

^aDepartment of Chemistry, Jining University, Shandong 273155, People's Republic of China
^*Correspondence e-mail: chunliangtianjn@163.com

(Received 10 November 2009; accepted 9 December 2009; online 16 December 2009)

The title complex, [Ni₂(C₆H₂N₃O₇)₂(C₁₀H₂₀N₄O₄)], contains a centrosymmetric binuclear unit in which the oxamide ligand (located on a centre of symmetry) acts in a bis-tetradentate fashion and the picrate anion binds to nickel(II) in a bidentate mode. The Ni^II atom displays a distorted octahedral coordination with axial elongation. The binuclear molecules are linked by intermolecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensonal supramolecular network extending parallel to (100).

Related literature

For background to oxamido compounds and their complexes, see: Ruiz et al. (1999 ); Ojima & Nonoyama (1988 ).

Experimental

Crystal data

[Ni₂(C₆H₂N₃O₇)₂(C₁₀H₂₀N₄O₄)]
M_r = 833.93
Triclinic, $[P \overline 1]$
a = 7.7893 (16) Å
b = 8.1405 (16) Å
c = 12.417 (3) Å
α = 98.00 (3)°
β = 99.00 (3)°
γ = 94.36 (3)°
V = 766.2 (3) Å³
Z = 1
Mo Kα radiation
μ = 1.33 mm⁻¹
T = 298 K
0.19 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.786, T_max = 0.879
4040 measured reflections
2703 independent reflections
2233 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.087
S = 1.23
2703 reflections
235 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—Ni1	1.903 (3)
N2—Ni1	2.032 (3)
O1—Ni1	1.991 (3)
O2—Ni1	2.537 (3)
O3—Ni1	1.942 (2)
O4—Ni1	2.561 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2C⋯O7ⁱ	0.91	2.15	3.054 (4)	171
O2—H2⋯O1ⁱⁱ	0.86	2.34	3.084 (4)	145
C10—H10⋯O5ⁱⁱⁱ	0.93	2.49	3.319 (5)	149
Symmetry codes: (i) -x, -y, -z+2; (ii) -x, -y, -z+1; (iii) x, y-1, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052933/si2223sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052933/si2223Isup2.hkl

checkCIF report

Comment top

Oxamido compounds and their complexes have been investigated extensively (Ruiz et al., 1999) by virtue of their bioactivities and the versatile bridging function (Ojima & Nonoyama, 1988). We selected N,N'-bis(3-aminopropyl)oxamide as a bridging ligand and picrate as a terminal group to synthesize a new binuclear nickel(II) compound, (I).

The title compound, (I) (Fig. 1), is a binuclear nickel(II) complex containing a total of 52 non-H atoms. Two terminal picrate ligands and a µ₃-trans-oxamidato bridge with an inversion centre at the mid-point of the C—C bond of the oxamide group. The geometry of each nickel(II) atom is distorted octahedral. For the Ni1, atoms O2 and O4 are in axial positions. The equatorial plane is composed of three atoms from the oxamide bridge (N1, N2, and O1) and the phenolic oxygen atom (O3) from the picrate ligand. The maximum displacement of the four atoms from the equatorial plane is 0.1117 (15) Å at N1, and the nickel(II) atom lies 0.0524 (8) Å out of the plane. The Ni—N bond lenghts (Table 1) are 1.903 (3) and 2.032 (3)Å, whereas the bond lengths of Ni1—O2 and Ni1—O4 are relatively long and can be considered as a (4+1+1) coordination. As a terminal group, the picrate anion assumes a bidentate mode, forming a six-membered chelate ring on the nickel(II) ion. The dihedral angle between the benzyl ring of the picrate ion and the equatorial plane is 88.28 (3)°.

The crystal structure is stabilized by hydrogen bonding. As shown in Fig. 2, a two-dimensional infinite network is formed via the N—H···O and O—H···O intermolecular hydrogen bonds. The adjacent layers are further connected by non-classical C—H···O hydrogen bonding contacts (Table 2) to form a two-dimensional supramolecular architecture in a zig-zag fashion parallel to the b,c plane (Fig. 2).

Related literature top

For background to oxamido compounds and their complexes, see: Ruiz et al. (1999); Ojima & Nonoyama, (1988).

Experimental top

To a stirred methanol solution (10 ml) containing Ni(pic)₂^.6H₂O (0.1255 g, 0.2 mmol) was added dropwise a ethanol solution (10 ml) of N,N'-bis(N-hydroxyethylaminoethyl)oxamide (0.0262 g, 0.1 mmol) and piperidine (0.0170 g, 0.2 mmol) at room temperature. The mixture was stirred quickly at 323 K for 8 h. The resulting solution was filtered and the filtrate was kept at room temperature. Green crystals suitable for X-ray analysis were obtained from the filtrate by slow evaporation for about two weeks.Yield, 46%, analysis, calculated for C₂₂H₂₄N₁₀O₁₈Ni₂: C 31.69, H, 2.90; N 16.80%; found: C 31.75, H 2.91, N, 16.82%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The binuclear complex of (I) with 30% displacement ellipsoids. [Symmetry code: A = -x, -y + 1, -z + 1]
	Fig. 2. A view of the three-dimensional hydrogen-bonding structure of (I). The H-bonds are shown as dotted lines. [Symmetry codes: i = -x, -y, -z + 2; ii = -x, -y, -z + 1; iii = x, y - 1, z]

{µ-trans-N,N'-Bis[2-(2- hydroxyethylamino)ethyl]oxamidato(2-)}bis[picratonickel(II)] top

Crystal data top

[Ni₂(C₆H₂N₃O₇)₂(C₁₀H₂₀N₄O₄)]	Z = 1
M_r = 833.93	F(000) = 426
Triclinic, P1	D_x = 1.807 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7893 (16) Å	Cell parameters from 1927 reflections
b = 8.1405 (16) Å	θ = 2.5–26.3°
c = 12.417 (3) Å	µ = 1.33 mm⁻¹
α = 98.00 (3)°	T = 298 K
β = 99.00 (3)°	Block, green
γ = 94.36 (3)°	0.19 × 0.14 × 0.10 mm
V = 766.2 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	2703 independent reflections
Radiation source: fine-focus sealed tube	2233 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 25.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.786, T_max = 0.879	k = −9→7
4040 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.23	w = 1/[σ²(F_o²) + (0.0205P)² + 0.7682P] where P = (F_o² + 2F_c²)/3
2703 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Ni₂(C₆H₂N₃O₇)₂(C₁₀H₂₀N₄O₄)]	γ = 94.36 (3)°
M_r = 833.93	V = 766.2 (3) Å³
Triclinic, P1	Z = 1
a = 7.7893 (16) Å	Mo Kα radiation
b = 8.1405 (16) Å	µ = 1.33 mm⁻¹
c = 12.417 (3) Å	T = 298 K
α = 98.00 (3)°	0.19 × 0.14 × 0.10 mm
β = 99.00 (3)°

Data collection top

Bruker SMART CCD diffractometer	2703 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2233 reflections with I > 2σ(I)
T_min = 0.786, T_max = 0.879	R_int = 0.015
4040 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.087	H-atom parameters constrained
S = 1.23	Δρ_max = 0.39 e Å⁻³
2703 reflections	Δρ_min = −0.30 e Å⁻³
235 parameters

Special details top

Experimental. a DELU restraint was applied for Ni1 O2 with s.u. 0.002.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.0883 (4)	0.5501 (4)	0.5131 (3)	0.0339 (8)
C2	0.3717 (5)	0.5619 (5)	0.6319 (3)	0.0446 (9)
H2A	0.3764	0.6824	0.6485	0.054*
H2B	0.4516	0.5339	0.5811	0.054*
C3	0.4200 (5)	0.4875 (5)	0.7369 (3)	0.0471 (10)
H3A	0.5460	0.4988	0.7586	0.057*
H3B	0.3704	0.5470	0.7960	0.057*
C4	0.4620 (5)	0.2008 (5)	0.6579 (4)	0.0553 (11)
H4A	0.5691	0.1901	0.7069	0.066*
H4B	0.4930	0.2524	0.5968	0.066*
C5	0.3688 (6)	0.0319 (5)	0.6149 (4)	0.0609 (12)
H5A	0.4466	−0.0410	0.5831	0.073*
H5B	0.3266	−0.0170	0.6740	0.073*
C6	−0.0763 (4)	0.1046 (4)	0.7864 (3)	0.0334 (8)
C7	−0.1144 (5)	0.2293 (4)	0.8705 (3)	0.0375 (8)
C8	−0.1927 (5)	0.1921 (5)	0.9576 (3)	0.0418 (9)
H8	−0.2158	0.2773	1.0098	0.050*
C9	−0.2359 (5)	0.0297 (5)	0.9669 (3)	0.0412 (9)
C10	−0.2086 (5)	−0.0995 (5)	0.8879 (3)	0.0415 (9)
H10	−0.2417	−0.2098	0.8935	0.050*
C11	−0.1322 (5)	−0.0607 (4)	0.8020 (3)	0.0361 (8)
N1	0.1953 (4)	0.4904 (4)	0.5843 (2)	0.0369 (7)
N2	0.3526 (4)	0.3088 (4)	0.7183 (2)	0.0415 (7)
H2C	0.3490	0.2754	0.7849	0.050*
N3	−0.0728 (5)	0.4047 (4)	0.8665 (3)	0.0477 (8)
N4	−0.3140 (4)	−0.0112 (6)	1.0595 (3)	0.0551 (9)
N5	−0.1030 (5)	−0.1992 (4)	0.7211 (3)	0.0502 (8)
O1	−0.1140 (3)	0.3225 (3)	0.5345 (2)	0.0428 (6)
O2	0.2266 (4)	0.0540 (4)	0.5331 (2)	0.0666 (8)
H2	0.1526	−0.0338	0.5205	0.080*
O3	−0.0095 (3)	0.1265 (3)	0.70232 (19)	0.0436 (6)
O4	0.0475 (5)	0.4475 (4)	0.8204 (3)	0.0690 (9)
O5	−0.1590 (4)	0.5052 (4)	0.9118 (3)	0.0659 (9)
O6	−0.3605 (5)	0.1016 (5)	1.1207 (3)	0.0776 (10)
O7	−0.3329 (4)	−0.1582 (5)	1.0716 (3)	0.0751 (10)
O8	−0.2239 (5)	−0.3026 (4)	0.6812 (3)	0.0860 (11)
O9	0.0423 (5)	−0.2056 (4)	0.6993 (3)	0.0839 (11)
Ni1	0.10416 (6)	0.29778 (6)	0.63579 (4)	0.03242 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.042 (2)	0.0292 (18)	0.0307 (18)	0.0014 (15)	0.0064 (15)	0.0059 (14)
C2	0.044 (2)	0.040 (2)	0.049 (2)	−0.0028 (18)	0.0027 (18)	0.0139 (18)
C3	0.050 (2)	0.042 (2)	0.044 (2)	−0.0062 (18)	−0.0010 (18)	0.0075 (18)
C4	0.047 (2)	0.053 (3)	0.066 (3)	0.008 (2)	0.007 (2)	0.013 (2)
C5	0.075 (3)	0.045 (3)	0.069 (3)	0.011 (2)	0.025 (3)	0.014 (2)
C6	0.0320 (18)	0.0347 (19)	0.0329 (19)	0.0005 (15)	0.0000 (15)	0.0111 (15)
C7	0.042 (2)	0.033 (2)	0.0366 (19)	0.0030 (16)	0.0029 (16)	0.0090 (16)
C8	0.039 (2)	0.051 (2)	0.034 (2)	0.0085 (18)	0.0046 (16)	0.0037 (17)
C9	0.037 (2)	0.057 (3)	0.0332 (19)	0.0033 (18)	0.0075 (16)	0.0150 (18)
C10	0.039 (2)	0.043 (2)	0.043 (2)	−0.0024 (17)	0.0038 (17)	0.0175 (18)
C11	0.038 (2)	0.037 (2)	0.0332 (19)	0.0017 (16)	0.0066 (15)	0.0068 (15)
N1	0.0415 (17)	0.0315 (16)	0.0375 (16)	−0.0006 (13)	0.0038 (14)	0.0102 (13)
N2	0.0489 (19)	0.0416 (18)	0.0341 (16)	0.0012 (15)	0.0034 (14)	0.0122 (14)
N3	0.063 (2)	0.0400 (19)	0.0382 (18)	0.0034 (17)	0.0061 (17)	0.0048 (15)
N4	0.047 (2)	0.083 (3)	0.0378 (19)	−0.001 (2)	0.0070 (16)	0.020 (2)
N5	0.065 (2)	0.0384 (19)	0.050 (2)	−0.0060 (18)	0.0203 (18)	0.0107 (16)
O1	0.0475 (15)	0.0405 (15)	0.0396 (14)	−0.0067 (12)	0.0017 (12)	0.0162 (11)
O2	0.075 (2)	0.0558 (18)	0.064 (2)	−0.0065 (15)	0.0163 (17)	−0.0078 (15)
O3	0.0592 (17)	0.0378 (15)	0.0348 (14)	−0.0045 (12)	0.0134 (12)	0.0086 (11)
O4	0.101 (3)	0.0412 (17)	0.067 (2)	−0.0132 (17)	0.0391 (19)	0.0013 (15)
O5	0.081 (2)	0.0470 (18)	0.071 (2)	0.0230 (17)	0.0149 (18)	0.0048 (15)
O6	0.080 (2)	0.108 (3)	0.0499 (19)	0.004 (2)	0.0307 (18)	0.0088 (19)
O7	0.083 (2)	0.091 (3)	0.063 (2)	0.001 (2)	0.0255 (18)	0.0423 (19)
O8	0.097 (3)	0.068 (2)	0.079 (2)	−0.030 (2)	0.018 (2)	−0.0194 (19)
O9	0.085 (3)	0.054 (2)	0.122 (3)	0.0086 (18)	0.060 (2)	−0.0012 (19)
Ni1	0.0384 (3)	0.0306 (2)	0.0281 (2)	−0.00288 (18)	0.00314 (18)	0.01040 (17)

Geometric parameters (Å, º) top

C1—O1ⁱ	1.282 (4)	C8—C9	1.364 (5)
C1—N1	1.289 (4)	C8—H8	0.9300
C1—C1ⁱ	1.510 (7)	C9—C10	1.387 (5)
C2—N1	1.451 (5)	C9—N4	1.449 (5)
C2—C3	1.520 (5)	C10—C11	1.363 (5)
C2—H2A	0.9700	C10—H10	0.9300
C2—H2B	0.9700	C11—N5	1.458 (5)
C3—N2	1.482 (5)	N1—Ni1	1.903 (3)
C3—H3A	0.9700	N2—Ni1	2.032 (3)
C3—H3B	0.9700	N2—H2C	0.9100
C4—N2	1.479 (5)	N3—O4	1.225 (4)
C4—C5	1.492 (6)	N3—O5	1.229 (4)
C4—H4A	0.9700	N4—O6	1.223 (5)
C4—H4B	0.9700	N4—O7	1.227 (5)
C5—O2	1.421 (5)	N5—O9	1.208 (4)
C5—H5A	0.9700	N5—O8	1.208 (4)
C5—H5B	0.9700	O1—C1ⁱ	1.282 (4)
C6—O3	1.266 (4)	O1—Ni1	1.991 (3)
C6—C11	1.431 (5)	O2—Ni1	2.537 (3)
C6—C7	1.433 (5)	O2—H2	0.8634
C7—C8	1.380 (5)	O3—Ni1	1.942 (2)
C7—N3	1.450 (5)	O4—Ni1	2.561 (3)

O1ⁱ—C1—N1	128.9 (3)	C10—C11—C6	125.0 (3)
O1ⁱ—C1—C1ⁱ	119.2 (4)	C10—C11—N5	117.1 (3)
N1—C1—C1ⁱ	111.9 (4)	C6—C11—N5	117.9 (3)
N1—C2—C3	106.0 (3)	C1—N1—C2	126.0 (3)
N1—C2—H2A	110.5	C1—N1—Ni1	115.6 (2)
C3—C2—H2A	110.5	C2—N1—Ni1	118.3 (2)
N1—C2—H2B	110.5	C4—N2—C3	112.9 (3)
C3—C2—H2B	110.5	C4—N2—Ni1	112.5 (2)
H2A—C2—H2B	108.7	C3—N2—Ni1	105.4 (2)
N2—C3—C2	109.9 (3)	C4—N2—H2C	108.6
N2—C3—H3A	109.7	C3—N2—H2C	108.6
C2—C3—H3A	109.7	Ni1—N2—H2C	108.6
N2—C3—H3B	109.7	O4—N3—O5	122.6 (4)
C2—C3—H3B	109.7	O4—N3—C7	119.3 (3)
H3A—C3—H3B	108.2	O5—N3—C7	118.0 (3)
N2—C4—C5	111.5 (3)	O6—N4—O7	123.2 (4)
N2—C4—H4A	109.3	O6—N4—C9	118.6 (4)
C5—C4—H4A	109.3	O7—N4—C9	118.2 (4)
N2—C4—H4B	109.3	O9—N5—O8	123.6 (4)
C5—C4—H4B	109.3	O9—N5—C11	117.9 (3)
H4A—C4—H4B	108.0	O8—N5—C11	118.5 (4)
O2—C5—C4	106.6 (4)	C1ⁱ—O1—Ni1	108.8 (2)
O2—C5—H5A	110.4	C5—O2—Ni1	99.8 (2)
C4—C5—H5A	110.4	C5—O2—H2	109.0
O2—C5—H5B	110.4	Ni1—O2—H2	110.6
C4—C5—H5B	110.4	C6—O3—Ni1	142.1 (2)
H5A—C5—H5B	108.6	N3—O4—Ni1	124.3 (2)
O3—C6—C11	119.7 (3)	N1—Ni1—O3	170.56 (12)
O3—C6—C7	127.8 (3)	N1—Ni1—O1	84.45 (11)
C11—C6—C7	112.5 (3)	O3—Ni1—O1	93.01 (11)
C8—C7—C6	123.2 (3)	N1—Ni1—N2	82.75 (12)
C8—C7—N3	116.3 (3)	O3—Ni1—N2	100.22 (12)
C6—C7—N3	120.5 (3)	O1—Ni1—N2	166.66 (11)
C9—C8—C7	119.7 (4)	N1—Ni1—O2	105.46 (11)
C9—C8—H8	120.1	O3—Ni1—O2	83.96 (11)
C7—C8—H8	120.1	O1—Ni1—O2	103.16 (11)
C8—C9—C10	121.2 (3)	N2—Ni1—O2	76.77 (12)
C8—C9—N4	120.3 (4)	N1—Ni1—O4	96.75 (11)
C10—C9—N4	118.5 (4)	O3—Ni1—O4	74.84 (10)
C11—C10—C9	118.3 (3)	O1—Ni1—O4	101.91 (12)
C11—C10—H10	120.8	N2—Ni1—O4	83.37 (12)
C9—C10—H10	120.8	O2—Ni1—O4	147.80 (11)

N1—C2—C3—N2	39.7 (4)	O5—N3—O4—Ni1	−138.5 (3)
N2—C4—C5—O2	66.6 (4)	C7—N3—O4—Ni1	42.8 (5)
O3—C6—C7—C8	178.0 (3)	C1—N1—Ni1—O3	−74.6 (8)
C11—C6—C7—C8	1.4 (5)	C2—N1—Ni1—O3	102.0 (7)
O3—C6—C7—N3	−1.3 (6)	C1—N1—Ni1—O1	0.2 (3)
C11—C6—C7—N3	−177.9 (3)	C2—N1—Ni1—O1	176.8 (3)
C6—C7—C8—C9	0.6 (5)	C1—N1—Ni1—N2	176.4 (3)
N3—C7—C8—C9	179.9 (3)	C2—N1—Ni1—N2	−7.0 (3)
C7—C8—C9—C10	−2.4 (5)	C1—N1—Ni1—O2	102.3 (3)
C7—C8—C9—N4	178.4 (3)	C2—N1—Ni1—O2	−81.1 (3)
C8—C9—C10—C11	2.0 (5)	C1—N1—Ni1—O4	−101.2 (3)
N4—C9—C10—C11	−178.8 (3)	C2—N1—Ni1—O4	75.4 (3)
C9—C10—C11—C6	0.2 (6)	C6—O3—Ni1—N1	−25.6 (10)
C9—C10—C11—N5	179.2 (3)	C6—O3—Ni1—O1	−99.7 (4)
O3—C6—C11—C10	−178.8 (3)	C6—O3—Ni1—N2	82.1 (4)
C7—C6—C11—C10	−1.8 (5)	C6—O3—Ni1—O2	157.4 (4)
O3—C6—C11—N5	2.3 (5)	C6—O3—Ni1—O4	1.9 (4)
C7—C6—C11—N5	179.2 (3)	C1ⁱ—O1—Ni1—N1	−0.3 (2)
O1ⁱ—C1—N1—C2	3.4 (6)	C1ⁱ—O1—Ni1—O3	170.6 (2)
C1ⁱ—C1—N1—C2	−176.4 (3)	C1ⁱ—O1—Ni1—N2	−16.7 (6)
O1ⁱ—C1—N1—Ni1	179.7 (3)	C1ⁱ—O1—Ni1—O2	−104.9 (2)
C1ⁱ—C1—N1—Ni1	−0.1 (5)	C1ⁱ—O1—Ni1—O4	95.5 (2)
C3—C2—N1—C1	160.4 (3)	C4—N2—Ni1—N1	−95.1 (3)
C3—C2—N1—Ni1	−15.9 (4)	C3—N2—Ni1—N1	28.3 (2)
C5—C4—N2—C3	−165.1 (3)	C4—N2—Ni1—O3	93.9 (3)
C5—C4—N2—Ni1	−46.0 (4)	C3—N2—Ni1—O3	−142.6 (2)
C2—C3—N2—C4	78.4 (4)	C4—N2—Ni1—O1	−78.6 (6)
C2—C3—N2—Ni1	−44.8 (4)	C3—N2—Ni1—O1	44.8 (6)
C8—C7—N3—O4	153.4 (4)	C4—N2—Ni1—O2	12.7 (2)
C6—C7—N3—O4	−27.3 (5)	C3—N2—Ni1—O2	136.1 (2)
C8—C7—N3—O5	−25.4 (5)	C4—N2—Ni1—O4	167.2 (3)
C6—C7—N3—O5	154.0 (3)	C3—N2—Ni1—O4	−69.4 (2)
C8—C9—N4—O6	9.2 (5)	C5—O2—Ni1—N1	98.6 (2)
C10—C9—N4—O6	−170.0 (4)	C5—O2—Ni1—O3	−81.9 (2)
C8—C9—N4—O7	−172.0 (4)	C5—O2—Ni1—O1	−173.6 (2)
C10—C9—N4—O7	8.8 (5)	C5—O2—Ni1—N2	20.1 (2)
C10—C11—N5—O9	−127.5 (4)	C5—O2—Ni1—O4	−33.3 (3)
C6—C11—N5—O9	51.5 (5)	N3—O4—Ni1—N1	147.0 (3)
C10—C11—N5—O8	51.1 (5)	N3—O4—Ni1—O3	−28.6 (3)
C6—C11—N5—O8	−129.9 (4)	N3—O4—Ni1—O1	61.3 (3)
C4—C5—O2—Ni1	−47.1 (3)	N3—O4—Ni1—N2	−131.1 (3)
C11—C6—O3—Ni1	−173.9 (3)	N3—O4—Ni1—O2	−79.2 (4)
C7—C6—O3—Ni1	9.7 (6)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O7ⁱⁱ	0.91	2.15	3.054 (4)	171
O2—H2···O1ⁱⁱⁱ	0.86	2.34	3.084 (4)	145
C10—H10···O5^iv	0.93	2.49	3.319 (5)	149

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

Experimental details

Crystal data
Chemical formula	[Ni₂(C₆H₂N₃O₇)₂(C₁₀H₂₀N₄O₄)]
M_r	833.93
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.7893 (16), 8.1405 (16), 12.417 (3)
α, β, γ (°)	98.00 (3), 99.00 (3), 94.36 (3)
V (Å³)	766.2 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.33
Crystal size (mm)	0.19 × 0.14 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.786, 0.879
No. of measured, independent and observed [I > 2σ(I)] reflections	4040, 2703, 2233
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.087, 1.23
No. of reflections	2703
No. of parameters	235
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

N1—Ni1	1.903 (3)	O2—Ni1	2.537 (3)
N2—Ni1	2.032 (3)	O3—Ni1	1.942 (2)
O1—Ni1	1.991 (3)	O4—Ni1	2.561 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O7ⁱ	0.91	2.15	3.054 (4)	171.2
O2—H2···O1ⁱⁱ	0.86	2.34	3.084 (4)	145.0
C10—H10···O5ⁱⁱⁱ	0.93	2.49	3.319 (5)	149.2

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

Acknowledgements

We acknowledge the financial support of the Science Foundation of Shandong.

References

Bruker, (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ojima, H. & Nonoyama, K. (1988). Coord. Chem. Rev. 92, 85–111. CrossRef CAS Web of Science Google Scholar
Ruiz, R., Faus, J., Lloret, F., Julve, M. & Journaurx, Y. (1999). Coord. Chem. Rev. 193–195, 1069–1117. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 1| January 2010| Page m71

doi:10.1107/S1600536809052933

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{μ-trans-N,N′-Bis[2-(2-hy­droxy­ethyl­amino)eth­yl]oxamidato(2−)}bis­­[picrato­nickel(II)]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{μ-trans-N,N′-Bis[2-(2-hydroxyethylamino)ethyl]oxamidato(2−)}bis[picratonickel(II)]