(3,3′-{(1E,1′E)-1,1′-[Ethane-1,2-diylbis(azan-1-yl-1-yl­idene-κN)]bis­(ethan-1-yl-1-yl­idene)}di­pyrazine 1-oxide-κN4)bis­(nitrato-κO)nickel(II) monohydrate

Omer, M.A.S.; Liu, J.-C.

doi:10.1107/S1600536813009355

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Pages m263-m264

https://doi.org/10.1107/S1600536813009355

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(3,3′-{(1E,1′E)-1,1′-[Ethane-1,2-diylbis(azan-1-yl-1-ylidene-κN)]bis(ethan-1-yl-1-ylidene)}dipyrazine 1-oxide-κN⁴)bis(nitrato-κO)nickel(II) monohydrate

Mohammed A. S. Omer ^a,^b and Jia-Cheng Liu ^a ^*

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China, and ^bDepartment of Chemistry, Faculty of Education, University of Khartoum, Sudan
^*Correspondence e-mail: jcliu8@nwnu.edu.cn

(Received 21 March 2013; accepted 6 April 2013; online 13 April 2013)

In the title complex, [Ni(NO₃)₂(C₁₄H₁₆N₆O₂)]·H₂O, the Ni^II atom, lying on a twofold rotation axis, is coordinated by a tetradentate 3,3′-{(1E,1′E)-1,1′-[ethane-1,2-diylbis(azan-1-yl-1-ylidene)]bis(ethan-1-yl-1-ylidene)}dipyrazine 1-oxide ligand and two mutually trans monodentate nitrate anions in a distorted octahedral geometry. The lattice water molecule is located on a twofold rotation axis. The complex molecules are linked by the water molecules through O—H⋯O hydrogen bonds into a chain along [001]. Further C—H⋯O hydrogen bonds lead to the formation of a three-dimensional network.

Related literature

For background to complexes with heterocyclic aromatic N-oxide ligands, see: Chupakhin et al. (2011 ); Karayannis et al. (1973 ); Nizhnik et al. (2008 ); Sarma et al. (2010 ). For related structures, see: Banerjee et al. (2004 ); Padhi & Manivannan (2007 ).

Experimental

Crystal data

[Ni(NO₃)₂(C₁₄H₁₆N₆O₂)]·H₂O
M_r = 501.05
Monoclinic, C 2/c
a = 16.993 (5) Å
b = 16.218 (5) Å
c = 7.754 (2) Å
β = 113.427 (3)°
V = 1960.8 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.793, T_max = 0.824
6930 measured reflections
1828 independent reflections
1515 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.070
S = 1.04
1828 reflections
151 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1W⋯O2ⁱ	0.78 (12)	2.46 (14)	3.086 (4)	139 (14)
C3—H3A⋯O2ⁱⁱ	0.93	2.58	3.389 (3)	146
C6—H6A⋯O1ⁱⁱⁱ	0.96	2.56	3.453 (4)	156
Symmetry codes: (i) x+1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813009355/hy2621sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009355/hy2621Isup2.hkl

checkCIF report

Comment top

Interest in heterocyclic aromatic N-oxides has flourished because of their practical impact on biological activity (Sarma et al., 2010). Several aromatic N-oxide derivatives capable of forming biologically active metal complexes have been reported (Nizhnik et al., 2008). Indeed, most coordinative studies of N-oxide donors have been carried out using pyridine-N-oxide (Karayannis et al., 1973) or bipyridine-N,N'-bisoxide. However, complexes containing ligands with pyrazine single N-oxide site are few (Chupakhin et al., 2011). Herein, we synthesize a new bipyrazine N-oxide Schiff base 3,3'-(1E,1'E)-1,1'-[ethane-1,2-diylbis(azan-1-yl-1-ylidene)] bis(ethan-1-yl-1-ylidene)dipyrazine-1-oxide (L) and its Ni(II) complex.

In the title complex, the Ni^II atom, lying on a twofold rotation axis, exhibits a distorted octahedral geometry, defined by four N atoms from the L ligand, occupying the equatorial plane, and two axial O atoms from two monodentate nitrate anions (Fig. 1). The equatorial Ni—N distances [Ni1—N1 = 2.0855 (19) and Ni1—N3 = 2.0183 (19) Å] are in a normal range for this class of compounds and also very similar to those of Ni—N(pyridine) and Ni—N(imine) found in analogue complexes (Banerjee et al., 2004; Padhi & Manivannan, 2007). Hydrogen bonding plays an important role in the formation of the crystal structure (Table 1). The lattice water molecule is located on a twofold rotation axis and connect two symmetry-related complex molecules through O—H···O hydrogen bonds, so forming a chain structure along [001] (Fig. 2). C—H···O hydrogen bonds lead to a three-dimensional network (Fig. 3).

Related literature top

For background to complexes with heterocyclic aromatic N-oxide ligands, see: Chupakhin et al. (2011); Karayannis et al. (1973); Nizhnik et al. (2008); Sarma et al. (2010). For related structures, see: Banerjee et al. (2004); Padhi & Manivannan (2007).

Experimental top

Synthesis of 2-acetylpyrazine-N-oxide: 2-Acetylpyrazine (12.2 g, 0.1 mol), glacial acetic acid (75 ml) and 30% hydrogen peroxide (14 ml) were heated with reflux at 70–80°C for 3 h. Additional 30% H₂O₂ (10 ml) was added and the temperature was maintained at 70–80°C for a further 10 h. The solvent was removed by rotary evaporation and upon standing brown yellow solid was formed, filtered and dried.

Synthesis of the L ligand : 1,2-Diaminoethane (0.100 g, 1.66 mmol) in 5 cm³ methanol was added dropwise to a hot stirred solution of 2-acetylpyrazine-N-oxide (0.455 g, 3.3 mmol) in 25 ml of methanol. The mixture was refluxed for 5 h. Brown precipitate was filtered, washed with methanol and air dried (yield: 0.68 g, 68.7%).

Synthesis of the title complex: Ni(NO₃)₂.6H₂O (0.290 g, 0.1 mmol) in 5 cm³ of CH₃CN was added dropwise to a hot stirred solution of the ligand L (0.030 g, 0.1 mmol) in a mixture of CH₃OH/CH₃CN (v/v = 2:1) and the mixture was stirred for 30 min. Diethyl ether was slowly diffused into the solution and block brown crystals suitable for X-ray diffraction analysis were collected by filtration within two weeks.

Structure description top

For background to complexes with heterocyclic aromatic N-oxide ligands, see: Chupakhin et al. (2011); Karayannis et al. (1973); Nizhnik et al. (2008); Sarma et al. (2010). For related structures, see: Banerjee et al. (2004); Padhi & Manivannan (2007).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level. H atoms and water molecule have been omitted for clarity. [Symmetry code: (i) -x, y, -z+1/2.]
	Fig. 2. : O—H···O hydrogen bonds (dashed lines) between water molecule and two adjacent complex molecules, which lead to a chain along [001]. H atoms not involved in hydrogen bonds are omitted for clarity.
	Fig. 3. The crystal packing of the title complex, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

(3,3'-{(1E,1'E)-1,1'-[Ethane-1,2-diylbis(azan-1-yl-1-ylidene-κN)]bis(ethan-1-yl-1-ylidene)}dipyrazine 1-oxide-κN⁴)bis(nitrato-κO)nickel(II) monohydrate top

Crystal data top

[Ni(NO₃)₂(C₁₄H₁₆N₆O₂)]·H₂O	F(000) = 1032
M_r = 501.05	D_x = 1.697 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2097 reflections
a = 16.993 (5) Å	θ = 2.5–23.4°
b = 16.218 (5) Å	µ = 1.06 mm⁻¹
c = 7.754 (2) Å	T = 293 K
β = 113.427 (3)°	Block, brown
V = 1960.8 (10) Å³	0.23 × 0.21 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1828 independent reflections
Radiation source: fine-focus sealed tube	1515 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.793, T_max = 0.824	k = −19→18
6930 measured reflections	l = −9→9

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0282P)² + 1.9388P] where P = (F_o² + 2F_c²)/3
1828 reflections	(Δ/σ)_max < 0.001
151 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

[Ni(NO₃)₂(C₁₄H₁₆N₆O₂)]·H₂O	V = 1960.8 (10) Å³
M_r = 501.05	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 16.993 (5) Å	µ = 1.06 mm⁻¹
b = 16.218 (5) Å	T = 293 K
c = 7.754 (2) Å	0.23 × 0.21 × 0.19 mm
β = 113.427 (3)°

Data collection top

Bruker APEXII CCD diffractometer	1828 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1515 reflections with I > 2σ(I)
T_min = 0.793, T_max = 0.824	R_int = 0.034
6930 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.26 e Å⁻³
1828 reflections	Δρ_min = −0.23 e Å⁻³
151 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	0.0000	0.22687 (3)	0.2500	0.02616 (14)
C1	0.11963 (16)	0.08324 (15)	0.4745 (4)	0.0364 (6)
H1	0.0798	0.0464	0.3947	0.044*
C2	0.19290 (17)	0.05229 (17)	0.6107 (4)	0.0461 (7)
H2	0.2022	−0.0043	0.6214	0.055*
C3	0.23627 (16)	0.18666 (15)	0.7095 (3)	0.0352 (6)
H3A	0.2760	0.2238	0.7884	0.042*
C4	0.16163 (14)	0.21473 (14)	0.5717 (3)	0.0282 (5)
C5	0.13925 (15)	0.30501 (15)	0.5473 (3)	0.0308 (5)
C6	0.19245 (18)	0.36564 (17)	0.6900 (4)	0.0528 (8)
H6A	0.1707	0.4202	0.6515	0.079*
H6B	0.2507	0.3625	0.7015	0.079*
H6C	0.1902	0.3533	0.8091	0.079*
C7	0.03112 (17)	0.40247 (15)	0.3526 (4)	0.0397 (6)
H7A	0.0746	0.4444	0.3731	0.048*
H7B	0.0006	0.4150	0.4319	0.048*
H1W	0.961 (7)	0.337 (9)	0.670 (19)	0.65 (10)*
N1	0.10253 (12)	0.16371 (12)	0.4506 (3)	0.0289 (5)
N2	0.25192 (14)	0.10433 (13)	0.7301 (3)	0.0437 (6)
N3	0.07187 (12)	0.32112 (11)	0.4021 (3)	0.0302 (5)
N4	−0.08220 (14)	0.16354 (17)	0.4974 (3)	0.0462 (6)
O1	0.32056 (13)	0.07731 (13)	0.8616 (3)	0.0739 (7)
O2	−0.06595 (11)	0.22970 (11)	0.4291 (2)	0.0413 (4)
O3	−0.11896 (19)	0.16980 (18)	0.6043 (4)	0.0997 (10)
O4	−0.06439 (14)	0.09594 (13)	0.4506 (3)	0.0603 (6)
O5	1.0000	0.3575 (3)	0.7500	0.0993 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0253 (2)	0.0206 (2)	0.0280 (2)	0.000	0.00583 (18)	0.000
C1	0.0348 (14)	0.0261 (14)	0.0407 (14)	−0.0021 (11)	0.0071 (12)	0.0025 (11)
C2	0.0413 (16)	0.0265 (14)	0.0576 (18)	0.0033 (12)	0.0059 (14)	0.0085 (13)
C3	0.0284 (14)	0.0325 (14)	0.0376 (14)	−0.0053 (11)	0.0055 (11)	0.0030 (11)
C4	0.0262 (12)	0.0287 (13)	0.0288 (12)	−0.0019 (10)	0.0100 (10)	0.0012 (10)
C5	0.0292 (14)	0.0282 (13)	0.0336 (13)	−0.0052 (11)	0.0110 (11)	−0.0025 (10)
C6	0.0490 (18)	0.0387 (17)	0.0501 (17)	−0.0044 (14)	−0.0021 (14)	−0.0097 (14)
C7	0.0454 (17)	0.0208 (13)	0.0458 (15)	0.0011 (11)	0.0106 (13)	−0.0029 (11)
N1	0.0278 (11)	0.0226 (10)	0.0336 (11)	−0.0015 (9)	0.0092 (9)	0.0011 (9)
N2	0.0331 (13)	0.0363 (13)	0.0476 (13)	0.0022 (10)	0.0011 (11)	0.0110 (10)
N3	0.0330 (12)	0.0218 (11)	0.0330 (11)	−0.0011 (9)	0.0102 (10)	−0.0021 (9)
N4	0.0339 (13)	0.0634 (17)	0.0408 (13)	−0.0025 (12)	0.0144 (11)	0.0077 (12)
O1	0.0487 (13)	0.0509 (14)	0.0815 (16)	0.0081 (11)	−0.0169 (12)	0.0172 (12)
O2	0.0453 (11)	0.0378 (10)	0.0453 (10)	0.0033 (9)	0.0226 (9)	0.0051 (9)
O3	0.118 (2)	0.125 (2)	0.100 (2)	0.0031 (19)	0.090 (2)	0.0153 (17)
O4	0.0714 (15)	0.0405 (12)	0.0721 (15)	−0.0098 (11)	0.0319 (12)	0.0052 (11)
O5	0.126 (4)	0.113 (3)	0.068 (2)	0.000	0.047 (2)	0.000

Geometric parameters (Å, º) top

Ni1—N3	2.0183 (19)	C5—C6	1.488 (3)
Ni1—N1	2.0855 (19)	C6—H6A	0.9600
Ni1—O2	2.1032 (17)	C6—H6B	0.9600
C1—N1	1.334 (3)	C6—H6C	0.9600
C1—C2	1.368 (3)	C7—N3	1.468 (3)
C1—H1	0.9300	C7—C7ⁱ	1.521 (5)
C2—N2	1.355 (3)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—N2	1.358 (3)	N2—O1	1.283 (3)
C3—C4	1.371 (3)	N4—O3	1.224 (3)
C3—H3A	0.9300	N4—O4	1.230 (3)
C4—N1	1.351 (3)	N4—O2	1.275 (3)
C4—C5	1.506 (3)	O5—H1W	0.780 (5)
C5—N3	1.274 (3)

N3—Ni1—N3ⁱ	81.53 (11)	N3—C5—C4	113.8 (2)
N3—Ni1—N1ⁱ	160.01 (8)	C6—C5—C4	120.1 (2)
N3ⁱ—Ni1—N1ⁱ	78.71 (8)	C5—C6—H6A	109.5
N3—Ni1—N1	78.71 (8)	C5—C6—H6B	109.5
N3ⁱ—Ni1—N1	160.01 (8)	H6A—C6—H6B	109.5
N1ⁱ—Ni1—N1	121.17 (11)	C5—C6—H6C	109.5
N3—Ni1—O2ⁱ	90.67 (7)	H6A—C6—H6C	109.5
N3ⁱ—Ni1—O2ⁱ	87.44 (7)	H6B—C6—H6C	109.5
N1ⁱ—Ni1—O2ⁱ	91.42 (7)	N3—C7—C7ⁱ	109.44 (14)
N1—Ni1—O2ⁱ	89.81 (7)	N3—C7—H7A	109.8
N3—Ni1—O2	87.44 (7)	C7ⁱ—C7—H7A	109.8
N3ⁱ—Ni1—O2	90.67 (7)	N3—C7—H7B	109.8
N1ⁱ—Ni1—O2	89.81 (7)	C7ⁱ—C7—H7B	109.8
N1—Ni1—O2	91.42 (7)	H7A—C7—H7B	108.2
O2ⁱ—Ni1—O2	177.50 (10)	C1—N1—C4	116.2 (2)
N1—C1—C2	123.2 (2)	C1—N1—Ni1	130.95 (16)
N1—C1—H1	118.4	C4—N1—Ni1	112.79 (15)
C2—C1—H1	118.4	O1—N2—C2	121.5 (2)
N2—C2—C1	119.9 (2)	O1—N2—C3	120.2 (2)
N2—C2—H2	120.1	C2—N2—C3	118.3 (2)
C1—C2—H2	120.1	C5—N3—C7	125.5 (2)
N2—C3—C4	119.7 (2)	C5—N3—Ni1	118.92 (16)
N2—C3—H3A	120.2	C7—N3—Ni1	114.52 (15)
C4—C3—H3A	120.2	O3—N4—O4	121.7 (3)
N1—C4—C3	122.7 (2)	O3—N4—O2	117.7 (3)
N1—C4—C5	115.32 (19)	O4—N4—O2	120.6 (2)
C3—C4—C5	122.0 (2)	N4—O2—Ni1	121.09 (16)
N3—C5—C6	126.1 (2)

N1—C1—C2—N2	0.4 (4)	C4—C3—N2—O1	−178.2 (2)
N2—C3—C4—N1	−1.4 (4)	C4—C3—N2—C2	0.8 (4)
N2—C3—C4—C5	177.5 (2)	C6—C5—N3—C7	−3.4 (4)
N1—C4—C5—N3	−7.4 (3)	C4—C5—N3—C7	174.4 (2)
C3—C4—C5—N3	173.6 (2)	C6—C5—N3—Ni1	−170.6 (2)
N1—C4—C5—C6	170.5 (2)	C4—C5—N3—Ni1	7.1 (3)
C3—C4—C5—C6	−8.5 (3)	C7ⁱ—C7—N3—C5	164.2 (3)
C2—C1—N1—C4	−1.0 (4)	C7ⁱ—C7—N3—Ni1	−28.1 (3)
C2—C1—N1—Ni1	176.96 (19)	N3ⁱ—Ni1—N3—C5	179.1 (2)
C3—C4—N1—C1	1.4 (3)	N1ⁱ—Ni1—N3—C5	170.39 (19)
C5—C4—N1—C1	−177.5 (2)	N1—Ni1—N3—C5	−3.94 (17)
C3—C4—N1—Ni1	−176.86 (18)	O2ⁱ—Ni1—N3—C5	−93.61 (18)
C5—C4—N1—Ni1	4.2 (2)	O2—Ni1—N3—C5	88.02 (18)
N3—Ni1—N1—C1	−178.5 (2)	N3ⁱ—Ni1—N3—C7	10.46 (13)
N3ⁱ—Ni1—N1—C1	−169.8 (2)	N1ⁱ—Ni1—N3—C7	1.8 (3)
N1ⁱ—Ni1—N1—C1	3.71 (19)	N1—Ni1—N3—C7	−172.56 (17)
O2ⁱ—Ni1—N1—C1	−87.8 (2)	O2ⁱ—Ni1—N3—C7	97.77 (17)
O2—Ni1—N1—C1	94.4 (2)	O2—Ni1—N3—C7	−80.60 (17)
N3—Ni1—N1—C4	−0.56 (15)	O3—N4—O2—Ni1	178.3 (2)
N3ⁱ—Ni1—N1—C4	8.2 (3)	O4—N4—O2—Ni1	−4.6 (3)
N1ⁱ—Ni1—N1—C4	−178.30 (17)	N3—Ni1—O2—N4	−134.41 (18)
O2ⁱ—Ni1—N1—C4	90.16 (15)	N3ⁱ—Ni1—O2—N4	144.10 (18)
O2—Ni1—N1—C4	−87.66 (15)	N1ⁱ—Ni1—O2—N4	65.39 (18)
C1—C2—N2—O1	178.7 (3)	N1—Ni1—O2—N4	−55.78 (18)
C1—C2—N2—C3	−0.3 (4)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···O2ⁱⁱ	0.78 (12)	2.46 (14)	3.086 (4)	139 (14)
C3—H3A···O2ⁱⁱⁱ	0.93	2.58	3.389 (3)	146
C6—H6A···O1^iv	0.96	2.56	3.453 (4)	156

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

Experimental details

Crystal data
Chemical formula	[Ni(NO₃)₂(C₁₄H₁₆N₆O₂)]·H₂O
M_r	501.05
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	16.993 (5), 16.218 (5), 7.754 (2)
β (°)	113.427 (3)
V (Å³)	1960.8 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.793, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	6930, 1828, 1515
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.070, 1.04
No. of reflections	1828
No. of parameters	151
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···O2ⁱ	0.78 (12)	2.46 (14)	3.086 (4)	139 (14)
C3—H3A···O2ⁱⁱ	0.93	2.58	3.389 (3)	146
C6—H6A···O1ⁱⁱⁱ	0.96	2.56	3.453 (4)	156

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

Acknowledgements

We are thankful for support of this study by the National Natural Science Foundation of China (No. 20871099) and the Gansu Provincial Natural Science Foundation of China (No. 0710RJZA113).

References

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