Diazido-(2,2'-bipyrid-yl)dimethanol-nickel(II).

The title complex, [Ni(N(3))(2)(C(10)H(8)N(2))(CH(3)OH)(2)], lies on a twofold roation axis which runs through the Ni(II) ion and the mid-point of the bipyridine ligand. The Ni(II) ion is coordinated in a distorted octa-hedral environment by two azide ligands in a trans configuration. The methanol ligands are in a cis configuration and their hy-droxy groups form intra-molecular O-H⋯(N,N) hydrogen bonds with the azide ligands.

Related literature

For related structures, see: Urtiaga et al. (1995 ▶); Phatchimkun et al. (2009 ▶); Kou et al. (2008 ▶); Hou (2008 ▶).

Experimental

Crystal data

[Ni(N3)2(C10H8N2)(CH4O)2]

M = 363.04

Monoclinic,

a = 16.8173 (15) Å

b = 13.4470 (12) Å

c = 7.1848 (6) Å

β = 111.238 (1)°

V = 1514.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.31 mm−1

T = 293 K

0.32 × 0.24 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.680, T max = 0.790

3647 measured reflections

1333 independent reflections

1247 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.210

S = 1.02

1333 reflections

106 parameters

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038377/lh5134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038377/lh5134Isup2.hkl

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

[Ni(N3)2(C10H8N2)(CH4O)2]	F(000) = 752
Mr = 363.04	Dx = 1.592 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1564 reflections
a = 16.8173 (15) Å	θ = 2.8–27.4°
b = 13.4470 (12) Å	µ = 1.31 mm−1
c = 7.1848 (6) Å	T = 293 K
β = 111.238 (1)°	Block, green
V = 1514.4 (2) Å3	0.32 × 0.24 × 0.19 mm
Z = 4

Bruker APEXII CCD diffractometer	1333 independent reflections
Radiation source: fine-focus sealed tube	1247 reflections with I > 2σ(I)
graphite	Rint = 0.012
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −15→20
Tmin = 0.680, Tmax = 0.790	k = −15→11
3647 measured reflections	l = −8→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1511P)2 + 7.4217P] where P = (Fo2 + 2Fc2)/3
1333 reflections	(Δ/σ)max = 0.011
106 parameters	Δρmax = 1.08 e Å−3
0 restraints	Δρmin = −0.68 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	1.0000	0.74532 (6)	0.2500	0.0357 (4)
O1	0.9127 (2)	0.6557 (3)	0.1994 (5)	0.0403 (8)
H1A	0.8679	0.6589	0.0766	0.048*
N1	0.9185 (2)	0.8653 (3)	0.2091 (5)	0.0267 (8)
N2	0.9797 (3)	0.7545 (3)	−0.0390 (6)	0.0331 (10)
N3	0.9118 (3)	0.7278 (3)	−0.1552 (6)	0.0393 (10)
N4	0.8473 (3)	0.7061 (5)	−0.2714 (8)	0.0713 (16)
C1	0.8326 (2)	0.8578 (3)	0.1560 (6)	0.0347 (10)
H1	0.8083	0.7953	0.1514	0.042*
C2	0.7806 (3)	0.9397 (4)	0.1091 (7)	0.0397 (11)
H2	0.7220	0.9327	0.0750	0.048*
C3	0.8157 (3)	1.0328 (4)	0.1126 (6)	0.0374 (10)
H3	0.7811	1.0889	0.0782	0.045*
C4	0.9035 (3)	1.0414 (3)	0.1684 (6)	0.0323 (9)
H4	0.9287	1.1033	0.1723	0.039*
C5	0.9526 (2)	0.9565 (3)	0.2179 (5)	0.0244 (8)
C6	0.9097 (4)	0.5858 (5)	0.3297 (8)	0.0599 (16)
H6A	0.9663	0.5619	0.4021	0.090*
H6B	0.8745	0.5317	0.2589	0.090*
H6C	0.8863	0.6138	0.4215	0.090*

	U11	U22	U33	U12	U13	U23
Ni1	0.0333 (6)	0.0382 (6)	0.0347 (6)	0.000	0.0114 (4)	0.000
O1	0.0367 (17)	0.0404 (19)	0.0380 (17)	−0.0107 (14)	0.0068 (13)	0.0056 (14)
N1	0.0201 (16)	0.0322 (18)	0.0275 (17)	−0.0002 (13)	0.0083 (13)	0.0000 (13)
N2	0.032 (2)	0.043 (2)	0.024 (2)	−0.0043 (14)	0.0095 (18)	0.0006 (13)
N3	0.048 (3)	0.041 (2)	0.031 (2)	−0.0041 (19)	0.016 (2)	0.0055 (17)
N4	0.057 (3)	0.100 (4)	0.042 (3)	−0.034 (3)	0.000 (2)	0.003 (3)
C1	0.0205 (19)	0.043 (3)	0.038 (2)	−0.0039 (17)	0.0078 (16)	0.0002 (18)
C2	0.024 (2)	0.054 (3)	0.041 (2)	0.0030 (19)	0.0108 (18)	−0.002 (2)
C3	0.029 (2)	0.043 (3)	0.037 (2)	0.0113 (18)	0.0087 (18)	0.0006 (18)
C4	0.031 (2)	0.033 (2)	0.032 (2)	0.0023 (17)	0.0103 (17)	−0.0023 (17)
C5	0.021 (2)	0.033 (2)	0.0198 (17)	0.0004 (15)	0.0069 (14)	−0.0010 (15)
C6	0.052 (3)	0.069 (4)	0.049 (3)	−0.024 (3)	0.008 (2)	0.008 (3)

Ni1—O1	1.831 (3)	C1—C2	1.370 (7)
Ni1—O1i	1.831 (3)	C1—H1	0.9300
Ni1—N2	1.982 (4)	C2—C3	1.380 (7)
Ni1—N2i	1.982 (4)	C2—H2	0.9300
Ni1—N1i	2.068 (4)	C3—C4	1.387 (6)
Ni1—N1	2.068 (4)	C3—H3	0.9300
O1—C6	1.340 (6)	C4—C5	1.379 (6)
O1—H1A	0.9300	C4—H4	0.9300
N1—C5	1.346 (5)	C5—C5i	1.490 (7)
N1—C1	1.358 (5)	C6—H6A	0.9600
N2—N3	1.199 (6)	C6—H6B	0.9600
N3—N4	1.142 (6)	C6—H6C	0.9600
O1—Ni1—O1i	97.7 (2)	N4—N3—N2	176.8 (5)
O1—Ni1—N2	90.64 (15)	N1—C1—C2	121.9 (4)
O1i—Ni1—N2	94.04 (16)	N1—C1—H1	119.1
O1—Ni1—N2i	94.04 (16)	C2—C1—H1	119.1
O1i—Ni1—N2i	90.64 (15)	C1—C2—C3	119.6 (4)
N2—Ni1—N2i	172.9 (2)	C1—C2—H2	120.2
O1—Ni1—N1i	169.78 (14)	C3—C2—H2	120.2
O1i—Ni1—N1i	92.41 (16)	C2—C3—C4	119.0 (4)
N2—Ni1—N1i	87.38 (14)	C2—C3—H3	120.5
N2i—Ni1—N1i	87.08 (15)	C4—C3—H3	120.5
O1—Ni1—N1	92.41 (16)	C5—C4—C3	118.8 (4)
O1i—Ni1—N1	169.78 (14)	C5—C4—H4	120.6
N2—Ni1—N1	87.08 (15)	C3—C4—H4	120.6
N2i—Ni1—N1	87.38 (14)	N1—C5—C4	122.5 (3)
N1i—Ni1—N1	77.48 (19)	N1—C5—C5i	113.9 (2)
C6—O1—Ni1	123.5 (3)	C4—C5—C5i	123.6 (2)
C6—O1—H1A	118.2	O1—C6—H6A	109.5
Ni1—O1—H1A	118.2	O1—C6—H6B	109.5
C5—N1—C1	118.2 (3)	H6A—C6—H6B	109.5
C5—N1—Ni1	117.0 (2)	O1—C6—H6C	109.5
C1—N1—Ni1	124.4 (3)	H6A—C6—H6C	109.5
N3—N2—Ni1	118.1 (3)	H6B—C6—H6C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1a···N3	0.93	2.25	2.721 (4)	111
O1—H1a···N4	0.93	2.48	3.227 (5)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1a⋯N3	0.93	2.25	2.721 (4)	111
O1—H1a⋯N4	0.93	2.48	3.227 (5)	137