(3,3'-{(1E,1'E)-1,1'-[Ethane-1,2-diylbis(azan-1-yl-1-yl-idene-κN)]bis-(ethan-1-yl-1-yl-idene)}di-pyrazine 1-oxide-κN (4))bis-(nitrato-κO)nickel(II) monohydrate.

In the title complex, [Ni(NO3)2(C14H16N6O2)]·H2O, the Ni(II) atom, lying on a twofold rotation axis, is coordinated by a tetra-dentate 3,3'-{(1E,1'E)-1,1'-[ethane-1,2-diylbis(azan-1-yl-1-yl-idene)]bis-(ethan-1-yl-1-yl-idene)}di-pyrazine 1-oxide ligand and two mutually trans monodentate nitrate anions in a distorted o-cta-hedral geometry. The lattice water mol-ecule is located on a twofold rotation axis. The complex mol-ecules are linked by the water mol-ecules 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 = 501.05

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.070

S = 1.04

1828 reflections

151 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009355/hy2621sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009355/hy2621Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(NO3)2(C14H16N6O2)]·H2O	F(000) = 1032
Mr = 501.05	Dx = 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

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

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(Fo2) + (0.0282P)2 + 1.9388P] where P = (Fo2 + 2Fc2)/3
1828 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.26 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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

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)

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···O1iv	0.96	2.56	3.453 (4)	156

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) ; (ii) ; (iii) .