Bis(dicyanamido-κN)bis-[2-(2-hydroxy-ethyl)pyridine-κN,O]nickel(II).

In the title complex, [Ni{N(CN)(2)}(2)(C(7)H(9)NO)(2)], the Ni(II) ion (site symmetry ) adopts a distorted trans-NiO(2)N(4) octa-hedral geometry. In the crystal, inter-molecular O-H⋯N hydrogen bonds link the mol-ecules, forming a chain along the c axis.

Related literature

For related structures, see: Boskovic et al. (2002 ▶); Sanudo et al. (2003 ▶).

Experimental

Crystal data

[Ni(C2N3)2(C7H9NO)2]

M = 437.11

Triclinic,

a = 8.1498 (1) Å

b = 8.76020 (11) Å

c = 8.9201 (12) Å

α = 100.841 (1)°

β = 110.588 (2)°

γ = 115.359 (2)°

V = 493.66 (7) Å3

Z = 1

Mo Kα radiation

μ = 1.02 mm−1

T = 298 K

0.28 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.764, T max = 0.863

2566 measured reflections

1718 independent reflections

1579 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.00

1718 reflections

133 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043359/hb5097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043359/hb5097Isup2.hkl

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

[Ni(C2N3)2(C7H9NO)2]	Z = 1
Mr = 437.11	F(000) = 226
Triclinic, P1	Dx = 1.47 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1498 (1) Å	Cell parameters from 1464 reflections
b = 8.76020 (11) Å	θ = 2.7–26.3°
c = 8.9201 (12) Å	µ = 1.01 mm−1
α = 100.841 (1)°	T = 298 K
β = 110.588 (2)°	Block, green
γ = 115.359 (2)°	0.28 × 0.20 × 0.15 mm
V = 493.66 (7) Å3

Bruker SMART CCD diffractometer	1718 independent reflections
Radiation source: fine-focus sealed tube	1579 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −9→9
Tmin = 0.764, Tmax = 0.863	k = −7→10
2566 measured reflections	l = −10→8

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.0746P] where P = (Fo2 + 2Fc2)/3
1718 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.22 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	0.5000	0.0000	0.5000	0.03081 (18)
N1	0.7472 (3)	0.2759 (3)	0.6426 (3)	0.0341 (5)
N2	0.4639 (3)	0.0453 (3)	0.2748 (3)	0.0415 (5)
N3	0.3758 (4)	0.1688 (4)	0.0579 (4)	0.0700 (9)
N4	0.0438 (5)	0.0438 (4)	−0.1949 (4)	0.0731 (9)
O1	0.2970 (3)	0.0824 (2)	0.5031 (2)	0.0411 (4)
H1	0.1971	0.0414	0.4067	0.062*
C1	0.3611 (5)	0.2644 (4)	0.6012 (4)	0.0548 (8)
H1A	0.2523	0.2612	0.6245	0.066*
H1B	0.3849	0.3390	0.5343	0.066*
C2	0.5577 (5)	0.3491 (4)	0.7713 (4)	0.0537 (8)
H2A	0.5771	0.4562	0.8495	0.064*
H2B	0.5422	0.2608	0.8249	0.064*
C3	0.7468 (4)	0.4061 (4)	0.7512 (3)	0.0418 (6)
C4	0.9168 (5)	0.5852 (4)	0.8400 (4)	0.0614 (9)
H4	0.9143	0.6738	0.9136	0.074*
C5	1.0883 (5)	0.6328 (4)	0.8202 (5)	0.0653 (9)
H5	1.2039	0.7528	0.8817	0.078*
C6	1.0887 (5)	0.5030 (4)	0.7096 (4)	0.0559 (8)
H6	1.2034	0.5326	0.6932	0.067*
C7	0.9155 (4)	0.3274 (4)	0.6227 (4)	0.0428 (6)
H7	0.9151	0.2392	0.5456	0.051*
C8	0.4109 (4)	0.0950 (4)	0.1684 (3)	0.0375 (6)
C9	0.1941 (5)	0.0937 (4)	−0.0759 (4)	0.0489 (7)

	U11	U22	U33	U12	U13	U23
Ni1	0.0250 (3)	0.0319 (3)	0.0300 (3)	0.0149 (2)	0.00897 (19)	0.01179 (19)
N1	0.0305 (11)	0.0347 (11)	0.0322 (10)	0.0171 (9)	0.0116 (9)	0.0121 (9)
N2	0.0354 (12)	0.0455 (13)	0.0324 (11)	0.0182 (11)	0.0097 (10)	0.0168 (10)
N3	0.0383 (14)	0.0750 (19)	0.0627 (17)	0.0120 (13)	0.0049 (13)	0.0479 (16)
N4	0.0540 (17)	0.096 (2)	0.0586 (17)	0.0432 (17)	0.0088 (15)	0.0389 (17)
O1	0.0317 (9)	0.0441 (10)	0.0426 (10)	0.0243 (8)	0.0104 (8)	0.0135 (8)
C1	0.0432 (16)	0.0479 (17)	0.079 (2)	0.0307 (14)	0.0288 (16)	0.0222 (16)
C2	0.0537 (18)	0.0443 (16)	0.0553 (18)	0.0233 (15)	0.0298 (15)	0.0066 (14)
C3	0.0383 (14)	0.0379 (14)	0.0383 (14)	0.0186 (12)	0.0138 (12)	0.0090 (12)
C4	0.055 (2)	0.0382 (16)	0.065 (2)	0.0180 (15)	0.0240 (17)	0.0000 (15)
C5	0.0440 (18)	0.0349 (16)	0.084 (2)	0.0086 (14)	0.0234 (17)	0.0074 (16)
C6	0.0350 (15)	0.0443 (16)	0.072 (2)	0.0136 (13)	0.0231 (15)	0.0168 (15)
C7	0.0343 (14)	0.0380 (14)	0.0502 (16)	0.0177 (12)	0.0188 (13)	0.0140 (13)
C8	0.0251 (12)	0.0406 (14)	0.0343 (13)	0.0117 (11)	0.0108 (11)	0.0133 (12)
C9	0.0486 (17)	0.0551 (17)	0.0520 (17)	0.0306 (15)	0.0239 (15)	0.0326 (15)

Ni1—N2i	2.065 (2)	C1—C2	1.506 (4)
Ni1—N2	2.065 (2)	C1—H1A	0.9700
Ni1—O1	2.0748 (16)	C1—H1B	0.9700
Ni1—O1i	2.0748 (16)	C2—C3	1.491 (4)
Ni1—N1	2.095 (2)	C2—H2A	0.9700
Ni1—N1i	2.095 (2)	C2—H2B	0.9700
N1—C7	1.337 (3)	C3—C4	1.381 (4)
N1—C3	1.353 (3)	C4—C5	1.365 (5)
N2—C8	1.142 (3)	C4—H4	0.9300
N3—C8	1.293 (3)	C5—C6	1.360 (5)
N3—C9	1.296 (4)	C5—H5	0.9300
N4—C9	1.127 (4)	C6—C7	1.372 (4)
O1—C1	1.422 (3)	C6—H6	0.9300
O1—H1	0.8200	C7—H7	0.9300
N2i—Ni1—N2	180.0	O1—C1—H1B	109.6
N2i—Ni1—O1	92.61 (8)	C2—C1—H1B	109.6
N2—Ni1—O1	87.39 (8)	H1A—C1—H1B	108.1
N2i—Ni1—O1i	87.39 (8)	C3—C2—C1	113.5 (3)
N2—Ni1—O1i	92.61 (8)	C3—C2—H2A	108.9
O1—Ni1—O1i	180.0	C1—C2—H2A	108.9
N2i—Ni1—N1	91.92 (8)	C3—C2—H2B	108.9
N2—Ni1—N1	88.08 (8)	C1—C2—H2B	108.9
O1—Ni1—N1	89.07 (7)	H2A—C2—H2B	107.7
O1i—Ni1—N1	90.93 (7)	N1—C3—C4	120.6 (3)
N2i—Ni1—N1i	88.08 (8)	N1—C3—C2	117.7 (2)
N2—Ni1—N1i	91.92 (8)	C4—C3—C2	121.7 (3)
O1—Ni1—N1i	90.93 (7)	C5—C4—C3	120.3 (3)
O1i—Ni1—N1i	89.07 (7)	C5—C4—H4	119.8
N1—Ni1—N1i	180.0	C3—C4—H4	119.8
C7—N1—C3	117.8 (2)	C6—C5—C4	119.4 (3)
C7—N1—Ni1	117.74 (17)	C6—C5—H5	120.3
C3—N1—Ni1	124.45 (18)	C4—C5—H5	120.3
C8—N2—Ni1	156.7 (2)	C5—C6—C7	118.3 (3)
C8—N3—C9	122.3 (3)	C5—C6—H6	120.8
C1—O1—Ni1	124.15 (16)	C7—C6—H6	120.8
C1—O1—H1	109.5	N1—C7—C6	123.6 (3)
Ni1—O1—H1	113.9	N1—C7—H7	118.2
O1—C1—C2	110.2 (2)	C6—C7—H7	118.2
O1—C1—H1A	109.6	N2—C8—N3	172.5 (3)
C2—C1—H1A	109.6	N4—C9—N3	173.2 (3)
N2i—Ni1—N1—C7	115.4 (2)	O1—C1—C2—C3	74.7 (3)
N2—Ni1—N1—C7	−64.6 (2)	C7—N1—C3—C4	−1.0 (4)
O1—Ni1—N1—C7	−152.00 (19)	Ni1—N1—C3—C4	−179.8 (2)
O1i—Ni1—N1—C7	28.00 (19)	C7—N1—C3—C2	179.1 (3)
N2i—Ni1—N1—C3	−65.8 (2)	Ni1—N1—C3—C2	0.3 (3)
N2—Ni1—N1—C3	114.2 (2)	C1—C2—C3—N1	−56.9 (4)
O1—Ni1—N1—C3	26.8 (2)	C1—C2—C3—C4	123.2 (3)
O1i—Ni1—N1—C3	−153.2 (2)	N1—C3—C4—C5	−0.5 (5)
O1—Ni1—N2—C8	9.2 (5)	C2—C3—C4—C5	179.4 (3)
O1i—Ni1—N2—C8	−170.8 (5)	C3—C4—C5—C6	1.3 (6)
N1—Ni1—N2—C8	−80.0 (5)	C4—C5—C6—C7	−0.6 (5)
N1i—Ni1—N2—C8	100.0 (5)	C3—N1—C7—C6	1.8 (4)
N2i—Ni1—O1—C1	84.2 (2)	Ni1—N1—C7—C6	−179.3 (2)
N2—Ni1—O1—C1	−95.8 (2)	C5—C6—C7—N1	−1.0 (5)
N1—Ni1—O1—C1	−7.7 (2)	Ni1—N2—C8—N3	104 (2)
N1i—Ni1—O1—C1	172.3 (2)	C9—N3—C8—N2	177 (2)
Ni1—O1—C1—C2	−34.9 (3)	C8—N3—C9—N4	172 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4ii	0.82	1.89	2.711 (3)	175

Table 1

Selected bond lengths (Å)

Ni1—N2	2.065 (2)
Ni1—O1	2.0748 (16)
Ni1—N1	2.095 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N4i	0.82	1.89	2.711 (3)	175

Symmetry code: (i) .