Bis(di-2-pyridylmethane­diol-κ3N,O,N′)nickel(II) dinitrate

Yu, S.M.; Song, Y.J.; Kim, K.C.; Kim, C.; Kim, Y.

doi:10.1107/S1600536809018728

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages m678-m679

doi:10.1107/S1600536809018728

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Bis(di-2-pyridylmethanediol-κ³N,O,N′)nickel(II) dinitrate

Seung Man Yu,^a Young Joo Song,^a Kang Chul Kim,^b Cheal Kim ^a ^* and Youngmee Kim ^c ^*

^aDepartment of Fine Chemistry and Eco-Product and Materials Education Center, Seoul National University of Technology, Seoul 139-743, Republic of Korea, ^bDepartment of Computer Engineering, Yeosu Campus, Chonnam National University, Yeosu 550-749, Republic of Korea, and ^cDepartment of Chemistry and Nano Science, Ewha Women's University, Seoul 120-750, Republic of Korea
^*Correspondence e-mail: chealkim@sunt.ac.kr, ymeekim@ewha.ac.kr

(Received 7 May 2009; accepted 18 May 2009; online 23 May 2009)

The title compound, [Ni(C₁₁H₁₀N₂O₂)₂](NO₃)₂, consists of an Ni^II atom coordinated by two tridentate chelating di-2-pyridylmethanediol [(2-py)₂C(OH)₂] ligands. The Ni^II atom is located on an inversion center. The geometry around the Ni^II atom is distorted octahedral. The gem-diol (2-py)₂C(OH)₂ ligand adopts the coordination mode η¹:η¹:η¹. The Ni—N and Ni—O bond lengths are typical for high-spin Ni^II in an octahedral environment [Ni—N = 2.094 (2) and 2.124 (3) Å, and Ni—O = 2.108 (3) Å]. One of the hydroxy H atoms is split over two positions which both interact with the nitrate anion. The occurence of different O—H⋯O hydrogen bonds leads to the formation of a layer parallel to the (101) plane.

Related literature

For background information, see: Efthymiou et al. (2006 ); Moragues-Cánovas et al. (2004 ); Papaefstathiou & Perlepes (2002 ); Papatriantafyllopoulou et al. (2007 ); Stoumpos et al. (2008 , 2009 ). For related structures, see: Li et al. (2005 ); Wang et al. (1986 ).

Experimental

Crystal data

[Ni(C₁₁H₁₀N₂O₂)₂](NO₃)₂
M_r = 587.15
Monoclinic, P 2₁ /n
a = 8.4077 (9) Å
b = 15.5098 (16) Å
c = 9.5556 (10) Å
β = 94.644 (2)°
V = 1242.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.85 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.03 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
7646 measured reflections
2442 independent reflections
1826 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.135
S = 1.06
2442 reflections
179 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4	0.82	2.22	2.810 (4)	129
O1—H1B⋯O3	0.86	2.13	2.933 (4)	155
O1—H1A⋯O5ⁱ	0.87	2.04	2.884 (4)	165
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018728/dn2454sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018728/dn2454Isup2.hkl

checkCIF report

Comment top

Di-2-pyridyl ketone ((py)₂CO) has been employed to form structurally interesting new complexes with 3 d-metal ions (Stoumpos et al., 2009). Water and alcohols (ROH) have been shown to add to the carbonyl group forming the ligands (2-py)₂C(OH)₂ [the gem-diol form of (2-py)₂CO] and (2-py)₂C(OR)(OH) [the hemiacetal form of (2- py)₂CO], respectively (Efthymiou et al., 2006). The neutral ligands (py)₂C(OH)₂ and (py)₂C(OR)(OH) coordinate to the metal centres as N,N',O chelates (Papaefstathiou & Perlepes, 2002). The different interesting coordination modes have been seen when the ligands (py)₂C(OH)₂ and (py)₂C(OR)(OH) are deprotonated to form mono- or dianion. The deprotonation of hydroxyl groups leads to a coordinative flexibility (Papatriantafyllopoulou et al., 2007; Stoumpos et al., 2008). Some Ni^II complexes of the neutral ligand, (py)₂C(OH)₂ have been structuraly characterized (Wang et al., 1986; Li et al., 2005), but no structure with a nitrate ion as the counter-ion has been reported to date.

The Ni^II atom is located on an inversion center and is coordinated by two tridentate chelating (2-py)₂C(OH)₂ ligand to form a distorted octahedral geometry. The gem-diol ligand (2-py)₂C(OH)₂ adopts the coordination mode η¹:η¹:η¹ (Fig. 1). The Ni—N and Ni—O bond lengths are typical for high-spin Ni(II) in octahedral environments [Ni—N = 2.094 (2) and 2.124 (3) Å, Ni—O = 2.108 (3) Å] (Moragues-Cánovas et al., 2004). The hydrogen attached to O1 is splitting on two positions which are both in interaction with the NO₃^- anion. The O—H···O hydrogen bonds build up a layer parallel to the (101) plane (Table 1, Fig. 2).

Related literature top

For background information, see: Efthymiou et al. (2006); Moragues-Cánovas et al. (2004); Papaefstathiou & Perlepes (2002); Papatriantafyllopoulou et al. (2007); Stoumpos et al. (2008, 2009). For related structures, see: Li et al. (2005); Wang et al. (1986).

Experimental top

36.7 mg (0.125 mmol) of Ni(NO₃)₂.6H₂O and 35.5 mg (0.25 mmol) of C₆H₅COONH₄ were dissolved in 4 ml water and carefully layered by 4 ml solution of amixture of acetone, methanol and ethanol (2/2/2) of di-2-pyridyl ketone ligand (46.1 mg, 0.25 mmol). Suitable crystals of the title compound for X-ray analysis were obtained in a few weeks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title complex with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii and hydrogen bonds are shown as dashed lines. [Symmetry code: (i) 1 - x, 1 - y, 1 - z].
	Fig. 2. Packing view down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.

Bis(di-2-pyridylmethanediol-κ³N,O,N')nickel(II) dinitrate top

Crystal data top

[Ni(C₁₁H₁₀N₂O₂)₂](NO₃)₂	F(000) = 604
M_r = 587.15	D_x = 1.570 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2352 reflections
a = 8.4077 (9) Å	θ = 2.5–25.6°
b = 15.5098 (16) Å	µ = 0.85 mm⁻¹
c = 9.5556 (10) Å	T = 293 K
β = 94.644 (2)°	Plate, pale brown
V = 1242.0 (2) Å³	0.20 × 0.10 × 0.03 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	1826 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.057
Graphite monochromator	θ_max = 26.0°, θ_min = 2.5°
ϕ and ω scans	h = −11→11
7646 measured reflections	k = −20→12
2442 independent reflections	l = −12→12

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0755P)² + 0.0426P] where P = (F_o² + 2F_c²)/3
2442 reflections	(Δ/σ)_max < 0.001
179 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Ni(C₁₁H₁₀N₂O₂)₂](NO₃)₂	V = 1242.0 (2) Å³
M_r = 587.15	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4077 (9) Å	µ = 0.85 mm⁻¹
b = 15.5098 (16) Å	T = 293 K
c = 9.5556 (10) Å	0.20 × 0.10 × 0.03 mm
β = 94.644 (2)°

Data collection top

Bruker SMART CCD diffractometer	1826 reflections with I > 2σ(I)
7646 measured reflections	R_int = 0.057
2442 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	Δρ_max = 0.49 e Å⁻³
2442 reflections	Δρ_min = −0.59 e Å⁻³
179 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.5000	0.5000	0.5000	0.0334 (2)
N1	0.3937 (3)	0.52480 (18)	0.2948 (3)	0.0389 (6)
N2	0.2830 (3)	0.54084 (17)	0.5703 (3)	0.0347 (6)
O1	0.5183 (3)	0.63487 (17)	0.4873 (2)	0.0574 (7)
H1A	0.5905	0.6553	0.4370	0.086*	0.50
H1B	0.5305	0.6590	0.5688	0.086*	0.50
O2	0.3337 (3)	0.74355 (14)	0.3938 (3)	0.0539 (6)
H2	0.3866	0.7720	0.4530	0.081*
C1	0.3774 (4)	0.4731 (2)	0.1816 (4)	0.0478 (9)
H1	0.4155	0.4169	0.1884	0.057*
C2	0.3053 (5)	0.5019 (3)	0.0558 (4)	0.0639 (11)
H2A	0.2927	0.4653	−0.0214	0.077*
C3	0.2515 (5)	0.5865 (3)	0.0458 (4)	0.0685 (12)
H3	0.2048	0.6076	−0.0389	0.082*
C4	0.2677 (4)	0.6386 (3)	0.1615 (4)	0.0562 (10)
H4	0.2310	0.6951	0.1573	0.067*
C5	0.3394 (4)	0.6055 (2)	0.2841 (3)	0.0394 (7)
C6	0.3583 (4)	0.6549 (2)	0.4213 (3)	0.0386 (7)
C7	0.2392 (3)	0.61766 (19)	0.5177 (3)	0.0353 (7)
C8	0.0989 (4)	0.6581 (2)	0.5451 (4)	0.0459 (8)
H8	0.0700	0.7112	0.5054	0.055*
C9	0.0030 (4)	0.6160 (3)	0.6345 (4)	0.0594 (10)
H9	−0.0919	0.6414	0.6569	0.071*
C10	0.0462 (4)	0.5378 (3)	0.6898 (4)	0.0521 (9)
H10	−0.0182	0.5097	0.7500	0.063*
C11	0.1873 (4)	0.5008 (2)	0.6552 (3)	0.0434 (8)
H11	0.2164	0.4470	0.6916	0.052*
N3	0.3476 (4)	0.7718 (2)	0.7595 (4)	0.0585 (8)
O3	0.4512 (4)	0.71600 (19)	0.7535 (3)	0.0755 (9)
O4	0.3188 (5)	0.8218 (2)	0.6577 (3)	0.1014 (12)
O5	0.2759 (4)	0.7785 (2)	0.8634 (4)	0.0834 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0362 (3)	0.0326 (3)	0.0319 (3)	0.0023 (2)	0.0050 (2)	−0.0004 (2)
N1	0.0396 (15)	0.0451 (16)	0.0326 (15)	0.0016 (11)	0.0079 (11)	−0.0016 (11)
N2	0.0340 (13)	0.0360 (15)	0.0343 (14)	0.0020 (11)	0.0047 (11)	−0.0012 (11)
O1	0.0609 (16)	0.0526 (16)	0.0587 (16)	−0.0010 (12)	0.0049 (13)	−0.0001 (12)
O2	0.0675 (17)	0.0363 (13)	0.0578 (16)	0.0069 (12)	0.0054 (12)	0.0050 (11)
C1	0.054 (2)	0.050 (2)	0.040 (2)	0.0031 (16)	0.0081 (16)	−0.0051 (16)
C2	0.084 (3)	0.072 (3)	0.036 (2)	−0.001 (2)	0.0032 (19)	−0.0137 (19)
C3	0.087 (3)	0.079 (3)	0.038 (2)	0.011 (2)	−0.004 (2)	0.006 (2)
C4	0.072 (3)	0.054 (2)	0.043 (2)	0.0102 (19)	0.0005 (18)	0.0078 (17)
C5	0.0418 (18)	0.0411 (19)	0.0363 (17)	0.0017 (14)	0.0095 (14)	0.0007 (14)
C6	0.0390 (18)	0.0349 (18)	0.0422 (18)	0.0031 (14)	0.0059 (14)	0.0046 (14)
C7	0.0365 (16)	0.0357 (17)	0.0336 (16)	0.0002 (13)	0.0026 (13)	−0.0053 (13)
C8	0.0391 (18)	0.048 (2)	0.050 (2)	0.0069 (15)	−0.0001 (15)	−0.0015 (15)
C9	0.040 (2)	0.075 (3)	0.065 (2)	0.0062 (19)	0.0128 (18)	−0.010 (2)
C10	0.047 (2)	0.064 (2)	0.047 (2)	−0.0077 (18)	0.0155 (16)	−0.0005 (18)
C11	0.0485 (18)	0.0451 (19)	0.0370 (17)	−0.0049 (16)	0.0053 (14)	0.0002 (15)
N3	0.067 (2)	0.047 (2)	0.061 (2)	−0.0010 (16)	0.0000 (17)	−0.0192 (17)
O3	0.077 (2)	0.077 (2)	0.0714 (19)	0.0337 (16)	0.0032 (15)	−0.0251 (15)
O4	0.173 (4)	0.056 (2)	0.071 (2)	0.016 (2)	−0.014 (2)	−0.0052 (16)
O5	0.071 (2)	0.092 (2)	0.092 (2)	0.0066 (16)	0.0358 (18)	−0.0195 (18)

Geometric parameters (Å, º) top

Ni1—N2	2.093 (2)	C2—H2A	0.9300
Ni1—N2ⁱ	2.093 (2)	C3—C4	1.367 (5)
Ni1—O1	2.102 (3)	C3—H3	0.9300
Ni1—O1ⁱ	2.102 (3)	C4—C5	1.372 (4)
Ni1—N1	2.123 (3)	C4—H4	0.9300
Ni1—N1ⁱ	2.123 (3)	C5—C6	1.515 (4)
N1—C5	1.334 (4)	C6—C7	1.528 (4)
N1—C1	1.345 (4)	C7—C8	1.380 (4)
N2—C7	1.333 (4)	C8—C9	1.385 (5)
N2—C11	1.340 (4)	C8—H8	0.9300
O1—C6	1.472 (4)	C9—C10	1.360 (5)
O1—H1A	0.8650	C9—H9	0.9300
O1—H1B	0.8625	C10—C11	1.382 (5)
O2—C6	1.412 (4)	C10—H10	0.9300
O2—H2	0.8200	C11—H11	0.9300
C1—C2	1.377 (5)	N3—O5	1.206 (4)
C1—H1	0.9300	N3—O3	1.233 (4)
C2—C3	1.388 (5)	N3—O4	1.253 (4)

N2—Ni1—N2ⁱ	180.0	C4—C3—C2	119.5 (4)
N2—Ni1—O1	77.70 (10)	C4—C3—H3	120.3
N2ⁱ—Ni1—O1	102.30 (10)	C2—C3—H3	120.3
N2—Ni1—O1ⁱ	102.30 (10)	C3—C4—C5	118.5 (4)
N2ⁱ—Ni1—O1ⁱ	77.70 (10)	C3—C4—H4	120.7
O1—Ni1—O1ⁱ	180.0	C5—C4—H4	120.7
N2—Ni1—N1	85.93 (9)	N1—C5—C4	122.7 (3)
N2ⁱ—Ni1—N1	94.07 (9)	N1—C5—C6	113.4 (3)
O1—Ni1—N1	78.10 (10)	C4—C5—C6	123.9 (3)
O1ⁱ—Ni1—N1	101.90 (10)	O2—C6—O1	113.6 (2)
N2—Ni1—N1ⁱ	94.07 (9)	O2—C6—C5	109.1 (3)
N2ⁱ—Ni1—N1ⁱ	85.93 (9)	O1—C6—C5	107.0 (2)
O1—Ni1—N1ⁱ	101.90 (10)	O2—C6—C7	112.8 (2)
O1ⁱ—Ni1—N1ⁱ	78.10 (10)	O1—C6—C7	106.4 (2)
N1—Ni1—N1ⁱ	180.000 (1)	C5—C6—C7	107.6 (2)
C5—N1—C1	119.1 (3)	N2—C7—C8	123.3 (3)
C5—N1—Ni1	110.9 (2)	N2—C7—C6	113.0 (2)
C1—N1—Ni1	130.0 (2)	C8—C7—C6	123.7 (3)
C7—N2—C11	118.7 (3)	C7—C8—C9	116.8 (3)
C7—N2—Ni1	111.76 (19)	C7—C8—H8	121.6
C11—N2—Ni1	129.5 (2)	C9—C8—H8	121.6
C6—O1—Ni1	99.56 (17)	C10—C9—C8	120.7 (3)
C6—O1—H1A	110.0	C10—C9—H9	119.7
Ni1—O1—H1A	117.0	C8—C9—H9	119.7
C6—O1—H1B	109.5	C9—C10—C11	119.0 (3)
Ni1—O1—H1B	112.6	C9—C10—H10	120.5
H1A—O1—H1B	107.8	C11—C10—H10	120.5
C6—O2—H2	109.5	N2—C11—C10	121.5 (3)
N1—C1—C2	121.2 (4)	N2—C11—H11	119.3
N1—C1—H1	119.4	C10—C11—H11	119.3
C2—C1—H1	119.4	O5—N3—O3	120.1 (4)
C1—C2—C3	119.0 (4)	O5—N3—O4	120.5 (4)
C1—C2—H2A	120.5	O3—N3—O4	119.4 (4)
C3—C2—H2A	120.5

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.82	2.22	2.810 (4)	129
O1—H1B···O3	0.86	2.13	2.933 (4)	155
O1—H1A···O5ⁱⁱ	0.87	2.04	2.884 (4)	165

Symmetry code: (ii) x+1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₁H₁₀N₂O₂)₂](NO₃)₂
M_r	587.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.4077 (9), 15.5098 (16), 9.5556 (10)
β (°)	94.644 (2)
V (Å³)	1242.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.20 × 0.10 × 0.03

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7646, 2442, 1826
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.135, 1.06
No. of reflections	2442
No. of parameters	179
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.59

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.82	2.22	2.810 (4)	129.1
O1—H1B···O3	0.86	2.13	2.933 (4)	155.0
O1—H1A···O5ⁱ	0.87	2.04	2.884 (4)	165.3

Symmetry code: (i) x+1/2, −y+3/2, z−1/2.

Acknowledgements

Financial support from the Korean Environment Ministry `ET–Human Resource Development Project' and the Korean Science and Engineering Foundation (grant No. R01-2008-000-20704-0) is gratefully acknowledged.

References

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