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Bis({1-[(1-imino­eth­yl)imino]­eth­yl}aza­nido-κ2N1,N5)nickel(II) methanol monosolvate

aKey Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: weitaibao@126.com

(Received 6 November 2012; accepted 15 November 2012; online 5 December 2012)

The title compound, [Ni(C4H8N3)2]·CH3OH, contains two independent NiII atoms, each located on an inversion center and coordinated by four N atoms from two 1-[(1-imino­eth­yl)imino]­eth­yl}aza­nide ligands in a square-planar geometry. N—H⋯N, N—H⋯O and O—H⋯N hydrogen bonds link the complex mol­ecules and methanol solvent mol­ecules into a corrugated layer parallel to (001).

Related literature

For structures and applications of related compounds, see: Aromi et al. (2011[Aromi, G., Barrios, L. A., Roubeau, O. & Gamez, P. (2011). Coord. Chem. Rev. 255, 485-546.]); Guzei et al. (2006[Guzei, I. A., Crozier, K. R., Nelson, K. J., Pinkert, J. C., Schoenfeldt, N. J., Shepardson, K. E. & McGaff, R. W. (2006). Inorg. Chim. Acta, 359, 1169-1176.]); Kopylovich et al. (2007[Kopylovich, M. N., Haukka, M., Kirillov, A. M., Kukushkin, V. Y. & Pombeiro, A. J. L. (2007). Chem. Eur. J. 13, 786-791.]); Kryatov et al. (2001[Kryatov, S. V., Nazarenko, A. Y., Smith, M. B. & Rybak-Akimova, E. V. (2001). Chem. Commun. pp. 1174-1175.]); Norrestam et al. (1983[Norrestam, R., Mertz, S. & Crossland, I. (1983). Acta Cryst. C39, 1554-1556.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C4H8N3)2]·CH4O

  • Mr = 287.02

  • Monoclinic, P 21 /c

  • a = 9.2768 (7) Å

  • b = 11.4347 (3) Å

  • c = 12.9774 (3) Å

  • β = 92.961 (3)°

  • V = 1374.77 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.41 mm−1

  • T = 298 K

  • 0.23 × 0.21 × 0.19 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.603, Tmax = 0.766

  • 9293 measured reflections

  • 2421 independent reflections

  • 1738 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.082

  • S = 1.04

  • 2421 reflections

  • 163 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1Ai 0.86 2.19 3.049 (3) 172
N2—H2⋯O1Aii 0.86 2.23 3.079 (3) 169
N4—H4⋯N3iii 0.86 2.44 3.264 (3) 160
N5—H5⋯N3 0.86 2.31 3.153 (3) 165
O1A—H1A4⋯N6 0.82 1.90 2.711 (3) 172
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Acetonitrile is one of the common solvents that is widely used to study processes in solution. With most 3d-transition metal ions, acetonitrile behaves as a relatively weak monodentate ligand (Kopylovich et al., 2007; Kryatov et al., 2001), providing inorganic chemists with a perfect media for numerous reactions. As a whole, metal-promoted reactions of nitriles have proven to be a significant tool for the synthesis of diverse compounds, and several reviews on this topic have appeared in literatures in the past decades (Aromi et al., 2011). However, a few reports showed the application of solvothermal synthetic techniques to reactions of nitriles with transition metal sources as a mean for the preparation of coordination compounds with molecular or extended structures (Guzei et al., 2006). Here we study reactions of 3d-transition metal ions with acetonitrile in order to understand the reaction system and elucidate structural features of the resultant mononuclear metal complexes.

The asymmetric unit of the title compound contains two independent NiII atoms, each of which lies on an inversion center, and a methanol molecule, as shown in Fig. 1. Each NiII atom is in a square-planar geometry, coordinated by four N atoms from two 1-[(1-iminoethyl)imino]ethyl}azanide ligands. Two six-membered rings around the NiII atom is slightly distorted toward a boat conformation. In one six-membered ring, Ni1 and N2 atoms exist in the apex positions, while in the other ring Ni2 and N5 atoms do. The bond distances in the ligands are very similar to those observed for the simple acetamidine molecule (Norrestam et al., 1983). In the crystal, the complex molecules are linked into a one-dimensional supramolecular architecture via N4—H4···N3i, N5—H5···N3 hydrogen bonds (Table 1) [symmetry code: (i) -x+1, -y+1, -z]. The one-dimensional architectures are further linked into a two-dimensional supramolecular structure with highly corrugated architecture via O—H···N and N—H···O hydrogen bonds between the ligands and the lattice methanol molecules, as shown in Fig. 2.

Related literature top

For structures and applications of related compounds, see: Aromi et al. (2011); Guzei et al. (2006); Kopylovich et al. (2007); Kryatov et al. (2001); Norrestam et al. (1983).

Experimental top

A mixture of Ni(NO3)2.6H2O (0.029 g, 0.1 mmol) in 12 ml of acetonitrile/methanol (3:1, v/v) and 0.1 ml of 2M NaOH solution was sealed in a Teflon-lined autoclave and heated under autogenous pressure to 160°C for 3 days and then allowed to cool to room temperature at a rate of 1°C per minute. Block-shaped tan crystals of the title complex were collected in 71% yield.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.96, N—H = 0.86 and O—H = 0.82 Å and with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(C, O).

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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) 1-x, 1-y, -z; (ii) 2-x, -y, -z.]
[Figure 2] Fig. 2. The two-dimensional supramolecular structure of the title complex.
Bis({1-[(1-iminoethyl)imino]ethyl}azanido- κ2N1,N5)nickel(II) methanol monosolvate top
Crystal data top
[Ni(C4H8N3)2]·CH4OF(000) = 608
Mr = 287.02Dx = 1.387 Mg m3
Dm = 1.37 Mg m3
Dm measured by not measured
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9999 reflections
a = 9.2768 (7) Åθ = 2.4–27.7°
b = 11.4347 (3) ŵ = 1.41 mm1
c = 12.9774 (3) ÅT = 298 K
β = 92.961 (3)°Block, green
V = 1374.77 (11) Å30.23 × 0.21 × 0.19 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
2421 independent reflections
Radiation source: fine-focus sealed tube1738 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 911
Tmin = 0.603, Tmax = 0.766k = 1313
9293 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0344P)2 + 0.7499P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2421 reflectionsΔρmax = 0.33 e Å3
163 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.051 (2)
Crystal data top
[Ni(C4H8N3)2]·CH4OV = 1374.77 (11) Å3
Mr = 287.02Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.2768 (7) ŵ = 1.41 mm1
b = 11.4347 (3) ÅT = 298 K
c = 12.9774 (3) Å0.23 × 0.21 × 0.19 mm
β = 92.961 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
2421 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1738 reflections with I > 2σ(I)
Tmin = 0.603, Tmax = 0.766Rint = 0.032
9293 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.082H-atom parameters constrained
S = 1.04Δρmax = 0.33 e Å3
2421 reflectionsΔρmin = 0.20 e Å3
163 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
xyzUiso*/Ueq
C10.8993 (3)0.3445 (2)0.0859 (3)0.0599 (8)
H1A0.92690.33050.15720.090*
H1B0.80740.38320.08100.090*
H1C0.97040.39290.05580.090*
C20.8886 (3)0.2297 (2)0.02917 (19)0.0394 (6)
C30.7796 (3)0.1309 (2)0.10996 (19)0.0383 (6)
C40.6614 (3)0.1373 (3)0.1938 (2)0.0578 (8)
H4A0.66470.06880.23650.087*
H4B0.67470.20570.23510.087*
H4C0.56950.14130.16320.087*
N10.9732 (2)0.14471 (17)0.05897 (16)0.0391 (5)
H11.02480.15770.11480.047*
N20.8599 (2)0.03823 (17)0.10115 (15)0.0379 (5)
H20.84600.01290.14930.045*
N30.7895 (2)0.22670 (18)0.05010 (16)0.0423 (5)
Ni11.00000.00000.00000.03187 (16)
C50.4642 (3)0.1559 (2)0.1102 (3)0.0606 (8)
H5A0.38620.11500.07460.091*
H5B0.46850.13440.18180.091*
H5C0.55350.13570.08050.091*
C60.4397 (3)0.2853 (2)0.1004 (2)0.0407 (6)
C70.3098 (3)0.4450 (2)0.1593 (2)0.0402 (6)
C80.2071 (4)0.4860 (2)0.2380 (2)0.0561 (8)
H8A0.25700.49010.30460.084*
H8B0.12820.43190.24070.084*
H8C0.17070.56200.21900.084*
N40.3630 (2)0.52029 (17)0.09697 (17)0.0423 (6)
H40.32960.59020.10140.051*
N50.5126 (2)0.34436 (18)0.03568 (17)0.0406 (5)
H50.57650.30500.00470.049*
N60.3410 (2)0.32978 (18)0.16225 (16)0.0431 (5)
Ni20.50000.50000.00000.03481 (17)
C1A0.1695 (5)0.1778 (3)0.3585 (3)0.0868 (12)
H1A10.26170.15560.38940.130*
H1A20.09620.12680.38260.130*
H1A30.14840.25700.37710.130*
O1A0.1728 (2)0.16916 (17)0.25194 (14)0.0601 (6)
H1A40.22420.22100.23020.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0588 (19)0.0430 (17)0.076 (2)0.0143 (15)0.0105 (16)0.0205 (15)
C20.0371 (15)0.0335 (14)0.0476 (15)0.0039 (12)0.0022 (12)0.0055 (11)
C30.0365 (14)0.0359 (14)0.0422 (14)0.0038 (12)0.0001 (11)0.0030 (11)
C40.0597 (19)0.0530 (18)0.0582 (18)0.0117 (15)0.0199 (15)0.0022 (14)
N10.0408 (12)0.0349 (11)0.0408 (12)0.0056 (10)0.0048 (10)0.0067 (9)
N20.0414 (13)0.0322 (11)0.0395 (12)0.0048 (10)0.0037 (9)0.0048 (9)
N30.0400 (13)0.0359 (12)0.0502 (13)0.0094 (10)0.0044 (10)0.0036 (10)
Ni10.0320 (3)0.0273 (3)0.0360 (3)0.00400 (18)0.00116 (18)0.00203 (18)
C50.064 (2)0.0380 (16)0.081 (2)0.0033 (15)0.0155 (17)0.0081 (15)
C60.0399 (15)0.0325 (13)0.0490 (16)0.0001 (12)0.0043 (12)0.0039 (12)
C70.0347 (15)0.0402 (15)0.0454 (15)0.0010 (12)0.0012 (12)0.0033 (12)
C80.0558 (18)0.0507 (19)0.063 (2)0.0025 (14)0.0164 (15)0.0092 (14)
N40.0429 (13)0.0323 (12)0.0521 (13)0.0071 (10)0.0051 (11)0.0004 (10)
N50.0389 (13)0.0343 (12)0.0484 (12)0.0081 (10)0.0023 (10)0.0000 (10)
N60.0426 (13)0.0376 (12)0.0493 (13)0.0005 (10)0.0061 (11)0.0016 (10)
Ni20.0339 (3)0.0292 (3)0.0413 (3)0.00597 (19)0.00096 (19)0.00100 (19)
C1A0.124 (4)0.078 (3)0.058 (2)0.018 (2)0.006 (2)0.0053 (19)
O1A0.0711 (15)0.0590 (13)0.0505 (12)0.0232 (11)0.0049 (10)0.0076 (10)
Geometric parameters (Å, º) top
C1—C21.506 (3)C5—H5C0.9600
C1—H1A0.9600C6—N51.296 (3)
C1—H1B0.9600C6—N61.348 (3)
C1—H1C0.9600C7—N41.297 (3)
C2—N11.295 (3)C7—N61.349 (3)
C2—N31.344 (3)C7—C81.507 (4)
C3—N21.296 (3)C8—H8A0.9600
C3—N31.344 (3)C8—H8B0.9600
C3—C41.506 (3)C8—H8C0.9600
C4—H4A0.9600N4—Ni21.848 (2)
C4—H4B0.9600N4—H40.8600
C4—H4C0.9600N5—Ni21.841 (2)
N1—Ni11.8452 (19)N5—H50.8600
N1—H10.8600Ni2—N5ii1.841 (2)
N2—Ni11.851 (2)Ni2—N4ii1.848 (2)
N2—H20.8600C1A—O1A1.388 (4)
Ni1—N1i1.8452 (19)C1A—H1A10.9600
Ni1—N2i1.851 (2)C1A—H1A20.9600
C5—C61.501 (3)C1A—H1A30.9600
C5—H5A0.9600O1A—H1A40.8200
C5—H5B0.9600
C2—C1—H1A109.5H5A—C5—H5C109.5
C2—C1—H1B109.5H5B—C5—H5C109.5
H1A—C1—H1B109.5N5—C6—N6125.6 (2)
C2—C1—H1C109.5N5—C6—C5119.2 (3)
H1A—C1—H1C109.5N6—C6—C5115.2 (2)
H1B—C1—H1C109.5N4—C7—N6125.3 (3)
N1—C2—N3126.1 (2)N4—C7—C8119.4 (2)
N1—C2—C1119.0 (2)N6—C7—C8115.3 (2)
N3—C2—C1114.9 (2)C7—C8—H8A109.5
N2—C3—N3126.4 (2)C7—C8—H8B109.5
N2—C3—C4119.8 (2)H8A—C8—H8B109.5
N3—C3—C4113.8 (2)C7—C8—H8C109.5
C3—C4—H4A109.5H8A—C8—H8C109.5
C3—C4—H4B109.5H8B—C8—H8C109.5
H4A—C4—H4B109.5C7—N4—Ni2129.69 (19)
C3—C4—H4C109.5C7—N4—H4115.2
H4A—C4—H4C109.5Ni2—N4—H4115.2
H4B—C4—H4C109.5C6—N5—Ni2129.70 (18)
C2—N1—Ni1129.87 (18)C6—N5—H5115.1
C2—N1—H1115.1Ni2—N5—H5115.1
Ni1—N1—H1115.1C6—N6—C7120.2 (2)
C3—N2—Ni1129.38 (18)N5ii—Ni2—N5180.00 (13)
C3—N2—H2115.3N5ii—Ni2—N490.74 (9)
Ni1—N2—H2115.3N5—Ni2—N489.26 (9)
C3—N3—C2119.1 (2)N5ii—Ni2—N4ii89.26 (9)
N1—Ni1—N1i180.00 (13)N5—Ni2—N4ii90.74 (9)
N1—Ni1—N288.73 (9)N4—Ni2—N4ii180.0
N1i—Ni1—N291.27 (9)O1A—C1A—H1A1109.5
N1—Ni1—N2i91.27 (9)O1A—C1A—H1A2109.5
N1i—Ni1—N2i88.73 (9)H1A1—C1A—H1A2109.5
N2—Ni1—N2i180.00 (17)O1A—C1A—H1A3109.5
C6—C5—H5A109.5H1A1—C1A—H1A3109.5
C6—C5—H5B109.5H1A2—C1A—H1A3109.5
H5A—C5—H5B109.5C1A—O1A—H1A4109.5
C6—C5—H5C109.5
N3—C2—N1—Ni16.0 (4)N6—C7—N4—Ni23.4 (4)
C1—C2—N1—Ni1173.5 (2)C8—C7—N4—Ni2174.9 (2)
N3—C3—N2—Ni16.1 (4)N6—C6—N5—Ni24.4 (4)
C4—C3—N2—Ni1173.7 (2)C5—C6—N5—Ni2175.8 (2)
N2—C3—N3—C21.7 (4)N5—C6—N6—C70.6 (4)
C4—C3—N3—C2178.2 (2)C5—C6—N6—C7179.6 (2)
N1—C2—N3—C34.4 (4)N4—C7—N6—C63.3 (4)
C1—C2—N3—C3175.1 (2)C8—C7—N6—C6175.1 (2)
C2—N1—Ni1—N21.8 (2)C6—N5—Ni2—N43.5 (2)
C2—N1—Ni1—N2i178.2 (2)C6—N5—Ni2—N4ii176.5 (2)
C3—N2—Ni1—N13.9 (2)C7—N4—Ni2—N5ii179.8 (2)
C3—N2—Ni1—N1i176.1 (2)C7—N4—Ni2—N50.2 (2)
Symmetry codes: (i) x+2, y, z; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1Aiii0.862.193.049 (3)172
N2—H2···O1Aiv0.862.233.079 (3)169
N4—H4···N3ii0.862.443.264 (3)160
N5—H5···N30.862.313.153 (3)165
O1A—H1A4···N60.821.902.711 (3)172
Symmetry codes: (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Ni(C4H8N3)2]·CH4O
Mr287.02
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.2768 (7), 11.4347 (3), 12.9774 (3)
β (°) 92.961 (3)
V3)1374.77 (11)
Z4
Radiation typeMo Kα
µ (mm1)1.41
Crystal size (mm)0.23 × 0.21 × 0.19
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.603, 0.766
No. of measured, independent and
observed [I > 2σ(I)] reflections
9293, 2421, 1738
Rint0.032
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.082, 1.04
No. of reflections2421
No. of parameters163
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.20

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1Ai0.862.193.049 (3)172
N2—H2···O1Aii0.862.233.079 (3)169
N4—H4···N3iii0.862.443.264 (3)160
N5—H5···N30.862.313.153 (3)165
O1A—H1A4···N60.821.902.711 (3)172
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z; (iii) x+1, y+1, z.
 

Footnotes

Additional correspondence author, e-mail: zhangnwnu@126.com.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 21064006 and 21161018), the Natural Science Foundation of Gansu Province (1010RJZA018) and the Program for Changjiang Scholars and the Innovative Research Team in Universities of the Ministry of Education of China (IRT1177).

References

First citationAromi, G., Barrios, L. A., Roubeau, O. & Gamez, P. (2011). Coord. Chem. Rev. 255, 485–546.  CAS
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