Bis[2-(pyridin-2-yl)ethanol-κ2N,O]bis­(thio­cyanato-κN)nickel(II)

Lv, L.; Qiu, X.; Yang, J.; Liu, S.; Li, D.

doi:10.1107/S1600536810046647

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1587

https://doi.org/10.1107/S1600536810046647

Open

access

Bis[2-(pyridin-2-yl)ethanol-κ²N,O]bis(thiocyanato-κN)nickel(II)

Lei Lv,^a Xiumin Qiu,^a Jie Yang,^a Shizheng Liu ^a and Dacheng Li ^a ^*

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lidacheng@lcu.edu.cn

(Received 1 November 2010; accepted 11 November 2010; online 17 November 2010)

In the title complex, [Ni(NCS)₂(C₇H₉NO)₂], the Ni^II atom is in a distorted octahedral coordination environment defined by two N atoms of the two thiocyanate ions and by the N and O atoms of the two chelating 2-(pyridin-2-yl)ethanol ligands. The complex molecule is located around a crystallographic inversion center. In the crystal, molecules are connected into a two-dimensional polymeric structure parallel to (100) by O—H⋯S hydrogen bonds.

Related literature

For related structures, see: Pan et al. (2007 ); Yu et al. (2010 ).

Experimental

Crystal data

[Ni(NCS)₂(C₇H₉NO)₂]
M_r = 421.17
Monoclinic, P 2₁ /c
a = 8.7197 (9) Å
b = 13.8634 (15) Å
c = 7.8655 (7) Å
β = 105.496 (2)°
V = 916.26 (16) Å³
Z = 2
Mo Kα radiation
μ = 1.30 mm⁻¹
T = 298 K
0.42 × 0.41 × 0.40 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.611, T_max = 0.624
4493 measured reflections
1616 independent reflections
1408 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.076
S = 1.07
1616 reflections
115 parameters
5 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N2	2.052 (2)
Ni1—N1	2.1011 (19)
Ni1—O1	2.1030 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S1ⁱ	0.93	2.66	3.2183 (19)	119
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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: https://doi.org/10.1107/S1600536810046647/gk2318sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046647/gk2318Isup2.hkl

checkCIF report

Comment top

Molecular materials with porous coordination frameworks have recently drawn considerable interest because of their attractive properties. The importance of the work in this area is the construction of porous materials from metal ions and organic ligands as building blocks. As a flexible ligand, 2-(hydroxyethyl)pyridine (hepH) can adopt a variety of possible binding modes. As a contribution to this field, we report here the synthesis and structure of the title compound.

In the title complex molecule, [Ni(SCN)₂(C₇H₉NO)₂], the nickel(II) atom displays a distorted octahedral coordination geometry, provided by two N atoms of two thiocyanate ions and by the N and O atoms of two 2-(hydroxyethyl)pyridine ligands. Bond lengths and angles involving the metal centre are typical and comparable with those observed in related Co^(II) complexes (Pan et al., 2007; Yu et al., 2010). In the crystal structure, molecules are linked through intermolecular O—H···S hydrogen bonds (Table 1).

Related literature top

For related structures, see: Pan et al. (2007); Yu et al. (2010).

Experimental top

To a stirred methanol (10 ml) and acetonitrile (10 ml) solution of NiCl₂.6H₂O (1 mmol, 238 mg) was added 2-(pyridyn-2-yl)ethanol (2 mmol, 246 mg) in 5 ml me thanol and tetramethylammonium hydroxide(0.4 mmol, 165 mg, 25% solution in water). After 30 min to the above solution was added KSCN (2 mmol, 194 mg) and the solution was stirred for additional 6 h. The resulting red solution was filtered and was allowed to stand at room temperature for about one week, whereupon blue block crystal, suitable for X-ray diffraction analysis, was obtained.

Structure description top

For related structures, see: Pan et al. (2007); Yu et al. (2010).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids. Atoms labelled with the suffix A are generated by the symmetry operation -x + 2,-y,-z.

Bis[2-(pyridin-2-yl)ethanol-κ²N,O]bis(thiocyanato- κN)nickel(II) top

Crystal data top

[Ni(NCS)₂(C₇H₉NO)₂]	F(000) = 436
M_r = 421.17	D_x = 1.527 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2904 reflections
a = 8.7197 (9) Å	θ = 2.4–28.0°
b = 13.8634 (15) Å	µ = 1.30 mm⁻¹
c = 7.8655 (7) Å	T = 298 K
β = 105.496 (2)°	Block, blue
V = 916.26 (16) Å³	0.42 × 0.41 × 0.40 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD diffractometer	1616 independent reflections
Radiation source: fine-focus sealed tube	1408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→8
T_min = 0.611, T_max = 0.624	k = −16→15
4493 measured reflections	l = −7→9

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0356P)² + 0.5792P] where P = (F_o² + 2F_c²)/3
1616 reflections	(Δ/σ)_max = 0.001
115 parameters	Δρ_max = 0.41 e Å⁻³
5 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Ni(NCS)₂(C₇H₉NO)₂]	V = 916.26 (16) Å³
M_r = 421.17	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7197 (9) Å	µ = 1.30 mm⁻¹
b = 13.8634 (15) Å	T = 298 K
c = 7.8655 (7) Å	0.42 × 0.41 × 0.40 mm
β = 105.496 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1616 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1408 reflections with I > 2σ(I)
T_min = 0.611, T_max = 0.624	R_int = 0.020
4493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	5 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.07	Δρ_max = 0.41 e Å⁻³
1616 reflections	Δρ_min = −0.55 e Å⁻³
115 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	1.0000	0.5000	0.0000	0.03039 (15)
S1	1.22010 (9)	0.69823 (5)	0.50929 (9)	0.0528 (2)
N1	0.7906 (2)	0.54485 (14)	0.0607 (2)	0.0341 (4)
N2	1.1214 (2)	0.57961 (15)	0.2136 (3)	0.0409 (5)
O1	0.9851 (2)	0.62603 (12)	−0.1523 (2)	0.0415 (4)
H1	1.0793	0.6489	−0.1717	0.050*
C1	0.8438 (3)	0.6798 (2)	−0.2289 (4)	0.0498 (7)
H1A	0.8409	0.6968	−0.3493	0.060*
H1B	0.8448	0.7391	−0.1630	0.060*
C2	0.6971 (3)	0.62185 (19)	−0.2278 (3)	0.0452 (6)
H2A	0.6039	0.6570	−0.2936	0.054*
H2B	0.7005	0.5613	−0.2886	0.054*
C3	0.6788 (3)	0.60033 (17)	−0.0472 (3)	0.0373 (5)
C4	0.5510 (3)	0.6363 (2)	0.0063 (4)	0.0484 (6)
H4	0.4762	0.6754	−0.0692	0.058*
C5	0.5344 (3)	0.6142 (2)	0.1710 (4)	0.0535 (7)
H5	0.4484	0.6374	0.2077	0.064*
C6	0.6478 (3)	0.5570 (2)	0.2799 (4)	0.0499 (7)
H6	0.6397	0.5409	0.3920	0.060*
C7	0.7733 (3)	0.52394 (19)	0.2214 (3)	0.0415 (6)
H7	0.8496	0.4854	0.2963	0.050*
C8	1.1618 (3)	0.62905 (16)	0.3352 (3)	0.0320 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0355 (2)	0.0261 (2)	0.0306 (2)	0.00073 (16)	0.01065 (17)	−0.00126 (16)
S1	0.0696 (5)	0.0394 (4)	0.0428 (4)	−0.0032 (3)	0.0034 (3)	−0.0099 (3)
N1	0.0367 (10)	0.0311 (10)	0.0352 (10)	0.0005 (8)	0.0107 (8)	−0.0025 (8)
N2	0.0445 (11)	0.0363 (11)	0.0409 (10)	−0.0004 (9)	0.0100 (9)	−0.0065 (8)
O1	0.0447 (9)	0.0338 (9)	0.0486 (10)	0.0025 (7)	0.0170 (8)	0.0102 (7)
C1	0.0591 (17)	0.0436 (15)	0.0482 (15)	0.0122 (12)	0.0168 (13)	0.0162 (12)
C2	0.0467 (15)	0.0452 (15)	0.0402 (13)	0.0105 (12)	0.0057 (11)	0.0042 (11)
C3	0.0365 (12)	0.0326 (12)	0.0409 (13)	−0.0014 (10)	0.0070 (10)	−0.0048 (10)
C4	0.0398 (13)	0.0425 (15)	0.0630 (17)	0.0045 (12)	0.0137 (12)	−0.0034 (12)
C5	0.0480 (15)	0.0498 (16)	0.0713 (19)	−0.0007 (13)	0.0310 (14)	−0.0105 (14)
C6	0.0558 (16)	0.0530 (16)	0.0485 (15)	−0.0084 (13)	0.0271 (13)	−0.0068 (13)
C7	0.0453 (14)	0.0429 (14)	0.0393 (13)	−0.0025 (11)	0.0163 (11)	0.0006 (11)
C8	0.0324 (12)	0.0273 (11)	0.0361 (11)	0.0002 (9)	0.0087 (9)	0.0011 (7)

Geometric parameters (Å, º) top

Ni1—N2	2.052 (2)	C2—C3	1.501 (3)
Ni1—N1	2.1011 (19)	C2—H2A	0.9700
Ni1—O1	2.1030 (15)	C2—H2B	0.9700
S1—C8	1.637 (2)	C3—C4	1.386 (4)
N1—C7	1.344 (3)	C4—C5	1.375 (4)
N1—C3	1.349 (3)	C4—H4	0.9300
N2—C8	1.153 (3)	C5—C6	1.374 (4)
O1—C1	1.428 (3)	C5—H5	0.9300
O1—H1	0.9300	C6—C7	1.375 (4)
C1—C2	1.513 (4)	C6—H6	0.9300
C1—H1A	0.9700	C7—H7	0.9300
C1—H1B	0.9700

N2ⁱ—Ni1—N2	180.00 (9)	O1—C1—H1B	109.5
N2ⁱ—Ni1—N1ⁱ	86.82 (8)	C2—C1—H1B	109.5
N2—Ni1—N1ⁱ	93.18 (8)	H1A—C1—H1B	108.1
N2ⁱ—Ni1—N1	93.18 (8)	C3—C2—C1	114.5 (2)
N2—Ni1—N1	86.82 (8)	C3—C2—H2A	108.6
N1ⁱ—Ni1—N1	180.0	C1—C2—H2A	108.6
N2ⁱ—Ni1—O1	92.32 (7)	C3—C2—H2B	108.6
N2—Ni1—O1	87.68 (7)	C1—C2—H2B	108.6
N1ⁱ—Ni1—O1	92.38 (7)	H2A—C2—H2B	107.6
N1—Ni1—O1	87.62 (7)	N1—C3—C4	121.2 (2)
N2ⁱ—Ni1—O1ⁱ	87.68 (7)	N1—C3—C2	117.8 (2)
N2—Ni1—O1ⁱ	92.32 (7)	C4—C3—C2	120.9 (2)
N1ⁱ—Ni1—O1ⁱ	87.62 (7)	C5—C4—C3	120.1 (3)
N1—Ni1—O1ⁱ	92.38 (7)	C5—C4—H4	119.9
O1—Ni1—O1ⁱ	180.00 (5)	C3—C4—H4	119.9
C7—N1—C3	118.1 (2)	C6—C5—C4	118.5 (3)
C7—N1—Ni1	118.18 (16)	C6—C5—H5	120.8
C3—N1—Ni1	123.47 (16)	C4—C5—H5	120.8
C8—N2—Ni1	167.28 (19)	C5—C6—C7	119.2 (3)
C1—O1—Ni1	126.06 (15)	C5—C6—H6	120.4
C1—O1—H1	117.0	C7—C6—H6	120.4
Ni1—O1—H1	117.0	N1—C7—C6	122.8 (3)
O1—C1—C2	110.9 (2)	N1—C7—H7	118.6
O1—C1—H1A	109.5	C6—C7—H7	118.6
C2—C1—H1A	109.5	N2—C8—S1	179.3 (2)

N2ⁱ—Ni1—N1—C7	121.90 (18)	N1—Ni1—O1—C1	−23.9 (2)
N2—Ni1—N1—C7	−58.10 (18)	O1—C1—C2—C3	65.5 (3)
O1—Ni1—N1—C7	−145.91 (18)	C7—N1—C3—C4	1.0 (3)
O1ⁱ—Ni1—N1—C7	34.09 (18)	Ni1—N1—C3—C4	−173.23 (18)
N2ⁱ—Ni1—N1—C3	−63.84 (19)	C7—N1—C3—C2	−178.9 (2)
N2—Ni1—N1—C3	116.16 (19)	Ni1—N1—C3—C2	6.9 (3)
O1—Ni1—N1—C3	28.35 (18)	C1—C2—C3—N1	−63.6 (3)
O1ⁱ—Ni1—N1—C3	−151.65 (18)	C1—C2—C3—C4	116.5 (3)
N1ⁱ—Ni1—N2—C8	176.2 (9)	N1—C3—C4—C5	−1.2 (4)
N1—Ni1—N2—C8	−3.8 (9)	C2—C3—C4—C5	178.7 (2)
O1—Ni1—N2—C8	84.0 (9)	C3—C4—C5—C6	0.7 (4)
O1ⁱ—Ni1—N2—C8	−96.0 (9)	C4—C5—C6—C7	0.0 (4)
N2ⁱ—Ni1—O1—C1	69.2 (2)	C3—N1—C7—C6	−0.4 (4)
N2—Ni1—O1—C1	−110.8 (2)	Ni1—N1—C7—C6	174.2 (2)
N1ⁱ—Ni1—O1—C1	156.1 (2)	C5—C6—C7—N1	−0.1 (4)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1ⁱⁱ	0.93	2.66	3.2183 (19)	119

Symmetry code: (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Ni(NCS)₂(C₇H₉NO)₂]
M_r	421.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.7197 (9), 13.8634 (15), 7.8655 (7)
β (°)	105.496 (2)
V (Å³)	916.26 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.42 × 0.41 × 0.40

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.611, 0.624
No. of measured, independent and observed [I > 2σ(I)] reflections	4493, 1616, 1408
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.076, 1.07
No. of reflections	1616
No. of parameters	115
No. of restraints	5
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.55

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—N2	2.052 (2)	Ni1—O1	2.1030 (15)
Ni1—N1	2.1011 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1ⁱ	0.93	2.66	3.2183 (19)	119.0

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

This work was supported by the Natural Science Foundation of China (grant No. 20671048, 21041002).

References

Pan, Y.-P., Li, D.-C. & Wang, D.-Q. (2007). Acta Cryst. E63, m3034. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yu, Y., Guo, Y., Wang, D. & Li, D. (2010). Acta Cryst. E66, m753. Web of Science CrossRef IUCr Journals Google Scholar