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

Tian, C.

doi:10.1107/S1600536809052933

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

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).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809052933/si2223sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809052933/si2223Isup2.hkl Contains datablock I

CCDC reference: 766907

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.035
wR factor = 0.087
Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    --  O1      ..       5.39 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    --  O2      ..       8.29 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    --  O4      ..       6.22 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5
PLAT432_ALERT_2_C Short Inter X...Y Contact  O9     ..  C1      ..       2.92 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         66

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         46
            C1  -N1  -NI1 -O3    -74.60  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         47
            C2  -N1  -NI1 -O3    102.00  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         56
            C6  -O3  -NI1 -N1    -25.60  1.00   1.555   1.555   1.555   1.555
PLAT793_ALERT_4_G The Model has Chirality at N2      (Verify) ....          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   6 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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)