Bis({1-[(1-imino-eth-yl)imino]-eth-yl}aza-nido-κ(2) N (1),N (5))nickel(II) methanol monosolvate.

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

Related literature

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

Crystal data

[Ni(C4H8N3)2]·CH4O

M = 287.02

Monoclinic,

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 ▶) T min = 0.603, T max = 0.766

9293 measured reflections

2421 independent reflections

1738 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 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

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

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046958/hy2604sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046958/hy2604Isup2.hkl

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

[Ni(C4H8N3)2]·CH4O	F(000) = 608
Mr = 287.02	Dx = 1.387 Mg m−3Dm = 1.37 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9999 reflections
a = 9.2768 (7) Å	θ = 2.4–27.7°
b = 11.4347 (3) Å	µ = 1.41 mm−1
c = 12.9774 (3) Å	T = 298 K
β = 92.961 (3)°	Block, green
V = 1374.77 (11) Å3	0.23 × 0.21 × 0.19 mm
Z = 4

Bruker APEXII CCD diffractometer	2421 independent reflections
Radiation source: fine-focus sealed tube	1738 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→11
Tmin = 0.603, Tmax = 0.766	k = −13→13
9293 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-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 reflections	Δρmax = 0.33 e Å−3
163 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.051 (2)

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
C1	0.8993 (3)	0.3445 (2)	0.0859 (3)	0.0599 (8)
H1A	0.9269	0.3305	0.1572	0.090*
H1B	0.8074	0.3832	0.0810	0.090*
H1C	0.9704	0.3929	0.0558	0.090*
C2	0.8886 (3)	0.2297 (2)	0.02917 (19)	0.0394 (6)
C3	0.7796 (3)	0.1309 (2)	−0.10996 (19)	0.0383 (6)
C4	0.6614 (3)	0.1373 (3)	−0.1938 (2)	0.0578 (8)
H4A	0.6647	0.0688	−0.2365	0.087*
H4B	0.6747	0.2057	−0.2351	0.087*
H4C	0.5695	0.1413	−0.1632	0.087*
N1	0.9732 (2)	0.14471 (17)	0.05897 (16)	0.0391 (5)
H1	1.0248	0.1577	0.1148	0.047*
N2	0.8599 (2)	0.03823 (17)	−0.10115 (15)	0.0379 (5)
H2	0.8460	−0.0129	−0.1493	0.045*
N3	0.7895 (2)	0.22670 (18)	−0.05010 (16)	0.0423 (5)
Ni1	1.0000	0.0000	0.0000	0.03187 (16)
C5	0.4642 (3)	0.1559 (2)	0.1102 (3)	0.0606 (8)
H5A	0.3862	0.1150	0.0746	0.091*
H5B	0.4685	0.1344	0.1818	0.091*
H5C	0.5535	0.1357	0.0805	0.091*
C6	0.4397 (3)	0.2853 (2)	0.1004 (2)	0.0407 (6)
C7	0.3098 (3)	0.4450 (2)	0.1593 (2)	0.0402 (6)
C8	0.2071 (4)	0.4860 (2)	0.2380 (2)	0.0561 (8)
H8A	0.2570	0.4901	0.3046	0.084*
H8B	0.1282	0.4319	0.2407	0.084*
H8C	0.1707	0.5620	0.2190	0.084*
N4	0.3630 (2)	0.52029 (17)	0.09697 (17)	0.0423 (6)
H4	0.3296	0.5902	0.1014	0.051*
N5	0.5126 (2)	0.34436 (18)	0.03568 (17)	0.0406 (5)
H5	0.5765	0.3050	0.0047	0.049*
N6	0.3410 (2)	0.32978 (18)	0.16225 (16)	0.0431 (5)
Ni2	0.5000	0.5000	0.0000	0.03481 (17)
C1A	0.1695 (5)	0.1778 (3)	0.3585 (3)	0.0868 (12)
H1A1	0.2617	0.1556	0.3894	0.130*
H1A2	0.0962	0.1268	0.3826	0.130*
H1A3	0.1484	0.2570	0.3771	0.130*
O1A	0.1728 (2)	0.16916 (17)	0.25194 (14)	0.0601 (6)
H1A4	0.2242	0.2210	0.2302	0.090*

	U11	U22	U33	U12	U13	U23
C1	0.0588 (19)	0.0430 (17)	0.076 (2)	0.0143 (15)	−0.0105 (16)	−0.0205 (15)
C2	0.0371 (15)	0.0335 (14)	0.0476 (15)	0.0039 (12)	0.0022 (12)	−0.0055 (11)
C3	0.0365 (14)	0.0359 (14)	0.0422 (14)	0.0038 (12)	−0.0001 (11)	0.0030 (11)
C4	0.0597 (19)	0.0530 (18)	0.0582 (18)	0.0117 (15)	−0.0199 (15)	−0.0022 (14)
N1	0.0408 (12)	0.0349 (11)	0.0408 (12)	0.0056 (10)	−0.0048 (10)	−0.0067 (9)
N2	0.0414 (13)	0.0322 (11)	0.0395 (12)	0.0048 (10)	−0.0037 (9)	−0.0048 (9)
N3	0.0400 (13)	0.0359 (12)	0.0502 (13)	0.0094 (10)	−0.0044 (10)	−0.0036 (10)
Ni1	0.0320 (3)	0.0273 (3)	0.0360 (3)	0.00400 (18)	−0.00116 (18)	−0.00203 (18)
C5	0.064 (2)	0.0380 (16)	0.081 (2)	0.0033 (15)	0.0155 (17)	0.0081 (15)
C6	0.0399 (15)	0.0325 (13)	0.0490 (16)	−0.0001 (12)	−0.0043 (12)	0.0039 (12)
C7	0.0347 (15)	0.0402 (15)	0.0454 (15)	−0.0010 (12)	−0.0012 (12)	−0.0033 (12)
C8	0.0558 (18)	0.0507 (19)	0.063 (2)	−0.0025 (14)	0.0164 (15)	−0.0092 (14)
N4	0.0429 (13)	0.0323 (12)	0.0521 (13)	0.0071 (10)	0.0051 (11)	−0.0004 (10)
N5	0.0389 (13)	0.0343 (12)	0.0484 (12)	0.0081 (10)	0.0023 (10)	0.0000 (10)
N6	0.0426 (13)	0.0376 (12)	0.0493 (13)	−0.0005 (10)	0.0061 (11)	0.0016 (10)
Ni2	0.0339 (3)	0.0292 (3)	0.0413 (3)	0.00597 (19)	0.00096 (19)	0.00100 (19)
C1A	0.124 (4)	0.078 (3)	0.058 (2)	−0.018 (2)	0.006 (2)	0.0053 (19)
O1A	0.0711 (15)	0.0590 (13)	0.0505 (12)	−0.0232 (11)	0.0049 (10)	−0.0076 (10)

C1—C2	1.506 (3)	C5—H5C	0.9600
C1—H1A	0.9600	C6—N5	1.296 (3)
C1—H1B	0.9600	C6—N6	1.348 (3)
C1—H1C	0.9600	C7—N4	1.297 (3)
C2—N1	1.295 (3)	C7—N6	1.349 (3)
C2—N3	1.344 (3)	C7—C8	1.507 (4)
C3—N2	1.296 (3)	C8—H8A	0.9600
C3—N3	1.344 (3)	C8—H8B	0.9600
C3—C4	1.506 (3)	C8—H8C	0.9600
C4—H4A	0.9600	N4—Ni2	1.848 (2)
C4—H4B	0.9600	N4—H4	0.8600
C4—H4C	0.9600	N5—Ni2	1.841 (2)
N1—Ni1	1.8452 (19)	N5—H5	0.8600
N1—H1	0.8600	Ni2—N5ii	1.841 (2)
N2—Ni1	1.851 (2)	Ni2—N4ii	1.848 (2)
N2—H2	0.8600	C1A—O1A	1.388 (4)
Ni1—N1i	1.8452 (19)	C1A—H1A1	0.9600
Ni1—N2i	1.851 (2)	C1A—H1A2	0.9600
C5—C6	1.501 (3)	C1A—H1A3	0.9600
C5—H5A	0.9600	O1A—H1A4	0.8200
C5—H5B	0.9600
C2—C1—H1A	109.5	H5A—C5—H5C	109.5
C2—C1—H1B	109.5	H5B—C5—H5C	109.5
H1A—C1—H1B	109.5	N5—C6—N6	125.6 (2)
C2—C1—H1C	109.5	N5—C6—C5	119.2 (3)
H1A—C1—H1C	109.5	N6—C6—C5	115.2 (2)
H1B—C1—H1C	109.5	N4—C7—N6	125.3 (3)
N1—C2—N3	126.1 (2)	N4—C7—C8	119.4 (2)
N1—C2—C1	119.0 (2)	N6—C7—C8	115.3 (2)
N3—C2—C1	114.9 (2)	C7—C8—H8A	109.5
N2—C3—N3	126.4 (2)	C7—C8—H8B	109.5
N2—C3—C4	119.8 (2)	H8A—C8—H8B	109.5
N3—C3—C4	113.8 (2)	C7—C8—H8C	109.5
C3—C4—H4A	109.5	H8A—C8—H8C	109.5
C3—C4—H4B	109.5	H8B—C8—H8C	109.5
H4A—C4—H4B	109.5	C7—N4—Ni2	129.69 (19)
C3—C4—H4C	109.5	C7—N4—H4	115.2
H4A—C4—H4C	109.5	Ni2—N4—H4	115.2
H4B—C4—H4C	109.5	C6—N5—Ni2	129.70 (18)
C2—N1—Ni1	129.87 (18)	C6—N5—H5	115.1
C2—N1—H1	115.1	Ni2—N5—H5	115.1
Ni1—N1—H1	115.1	C6—N6—C7	120.2 (2)
C3—N2—Ni1	129.38 (18)	N5ii—Ni2—N5	180.00 (13)
C3—N2—H2	115.3	N5ii—Ni2—N4	90.74 (9)
Ni1—N2—H2	115.3	N5—Ni2—N4	89.26 (9)
C3—N3—C2	119.1 (2)	N5ii—Ni2—N4ii	89.26 (9)
N1—Ni1—N1i	180.00 (13)	N5—Ni2—N4ii	90.74 (9)
N1—Ni1—N2	88.73 (9)	N4—Ni2—N4ii	180.0
N1i—Ni1—N2	91.27 (9)	O1A—C1A—H1A1	109.5
N1—Ni1—N2i	91.27 (9)	O1A—C1A—H1A2	109.5
N1i—Ni1—N2i	88.73 (9)	H1A1—C1A—H1A2	109.5
N2—Ni1—N2i	180.00 (17)	O1A—C1A—H1A3	109.5
C6—C5—H5A	109.5	H1A1—C1A—H1A3	109.5
C6—C5—H5B	109.5	H1A2—C1A—H1A3	109.5
H5A—C5—H5B	109.5	C1A—O1A—H1A4	109.5
C6—C5—H5C	109.5
N3—C2—N1—Ni1	6.0 (4)	N6—C7—N4—Ni2	−3.4 (4)
C1—C2—N1—Ni1	−173.5 (2)	C8—C7—N4—Ni2	174.9 (2)
N3—C3—N2—Ni1	6.1 (4)	N6—C6—N5—Ni2	−4.4 (4)
C4—C3—N2—Ni1	−173.7 (2)	C5—C6—N5—Ni2	175.8 (2)
N2—C3—N3—C2	−1.7 (4)	N5—C6—N6—C7	0.6 (4)
C4—C3—N3—C2	178.2 (2)	C5—C6—N6—C7	−179.6 (2)
N1—C2—N3—C3	−4.4 (4)	N4—C7—N6—C6	3.3 (4)
C1—C2—N3—C3	175.1 (2)	C8—C7—N6—C6	−175.1 (2)
C2—N1—Ni1—N2	−1.8 (2)	C6—N5—Ni2—N4	3.5 (2)
C2—N1—Ni1—N2i	178.2 (2)	C6—N5—Ni2—N4ii	−176.5 (2)
C3—N2—Ni1—N1	−3.9 (2)	C7—N4—Ni2—N5ii	−179.8 (2)
C3—N2—Ni1—N1i	176.1 (2)	C7—N4—Ni2—N5	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1Aiii	0.86	2.19	3.049 (3)	172
N2—H2···O1Aiv	0.86	2.23	3.079 (3)	169
N4—H4···N3ii	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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1A i	0.86	2.19	3.049 (3)	172
N2—H2⋯O1A ii	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) ; (ii) ; (iii) .