Tetra­pyridine­bis(trichloro­acetato)nickel(II)

Li, L.-M.; Jian, F.-F.; Ren, X.-Y.

doi:10.1107/S1600536809030025

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1041

doi:10.1107/S1600536809030025

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Tetrapyridinebis(trichloroacetato)nickel(II)

Li-Min Li,^a Fang-Fang Jian ^b ^* and Xiao-Yan Ren ^b

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 27 July 2009; accepted 29 July 2009; online 8 August 2009)

The title compound, [Ni(C₂Cl₃O₂)₂(C₅H₅N)₄], was prepared by the reaction of pyridine and trichloroacetatonickel(II) in ethanol solution at room temperature. The Ni^II atom is located on a twofold rotation axis and has a slightly distorted octahedral coordination made up of four N atoms of the pyridine ligands and two O atoms of trichloroacetate anions. The molecular structure and packing are stabilized by intra- and intermolecular C—H⋯O hydrogen-bonding interactions.

Related literature

For the structural and magnetic properties of transition metal complexes involving a pyridine or a substituted pyridine ligand, see: Crawford & Hatfield (1977 ); Marsh et al. (1981 ); Swank & Willett (1980 ). For Ni—O and Ni—N bond lengths, see: Bentiss et al. (2002 ); Rodopoulos et al. (2001 ).

Experimental

Crystal data

[Ni(C₂Cl₃O₂)₂(C₅H₅N)₄]
M_r = 699.85
Monoclinic, C 2/c
a = 9.1073 (18) Å
b = 17.078 (3) Å
c = 19.376 (6) Å
β = 106.94 (3)°
V = 2882.9 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.27 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
13819 measured reflections
3312 independent reflections
2898 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.187
S = 1.07
3312 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 1.63 e Å⁻³
Δρ_min = −1.04 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4A—H4AA⋯O1ⁱ	0.93	2.55	3.442 (7)	162
C1B—H1BA⋯O2	0.93	2.59	2.943 (6)	103
C1A—H1AA⋯O1ⁱⁱ	0.93	2.41	3.253 (7)	151
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y, -z+{\script{1\over 2}}]$ .

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 global, I. DOI: 10.1107/S1600536809030025/at2853sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030025/at2853Isup2.hkl

checkCIF report

Comment top

The structural and magnetic properties of transition metal complexes in the solid state have been the subjects of numerous recent publications. This is particularly true for the cases where L is pyridine or a substituted pyridine (Swank & Willett, 1980; Marsh et al., 1981; Crawford & Hatfield, 1977). Much of this work has been concerned with the correlation of the structural properties of these complexes with their magnetic properties. In order to search for new complexes of this type, we synthesized the title compound and report its crystal structure here.

The title compound contains one nickel(II), four pyridine ligands and two trichloroacetic acid molecules. The coordination sphere of the nickel(II) ion is best described as a slightly distorted octahedron. The Ni—O and Ni—N bond lengths are in agreement with those reported recently (Bentiss et al., 2002; Rodopoulos et al., 2001). The crystal packing is stabilized by C—H···O intra- and intermolecular hydrogen interaction (Table 1).

Related literature top

For the structural and magnetic properties of transition metal complexes involving a pyridine or a substituted

pyridine ligand, see: Crawford & Hatfield (1977); Marsh et al. (1981); Swank & Willett (1980). For Ni—O and Ni—N

bond lengths, see: Bentiss et al. (2002); Rodopoulos et al. (2001).

Experimental top

The title compound was obtained by adding pyridine (4 mmol) dropwise to a solution of nickel(II) trichloroacetic acid (1 mmol) in ethanol (30 ml) under stirred for 1 h at room temperature. A green solution was formed and after a few days block crystals precipitated.

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. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Tetrapyridinebis(trichloroacetato)nickel(II) top

Crystal data top

[Ni(C₂Cl₃O₂)₂(C₅H₅N)₄]	F(000) = 1416
M_r = 699.85	D_x = 1.612 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2898 reflections
a = 9.1073 (18) Å	θ = 3.1–27.5°
b = 17.078 (3) Å	µ = 1.27 mm⁻¹
c = 19.376 (6) Å	T = 293 K
β = 106.94 (3)°	Block, green
V = 2882.9 (12) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2898 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −11→11
13819 measured reflections	k = −22→22
3312 independent reflections	l = −25→25

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.187	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0862P)² + 12.4612P] where P = (F_o² + 2F_c²)/3
3312 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 1.63 e Å⁻³
0 restraints	Δρ_min = −1.04 e Å⁻³

Crystal data top

[Ni(C₂Cl₃O₂)₂(C₅H₅N)₄]	V = 2882.9 (12) Å³
M_r = 699.85	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 9.1073 (18) Å	µ = 1.27 mm⁻¹
b = 17.078 (3) Å	T = 293 K
c = 19.376 (6) Å	0.30 × 0.20 × 0.10 mm
β = 106.94 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2898 reflections with I > 2σ(I)
13819 measured reflections	R_int = 0.054
3312 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.187	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0862P)² + 12.4612P] where P = (F_o² + 2F_c²)/3
3312 reflections	Δρ_max = 1.63 e Å⁻³
177 parameters	Δρ_min = −1.04 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Ni	0.0000	0.03441 (4)	0.2500	0.0324 (2)
Cl1	0.1137 (2)	0.13260 (11)	0.03902 (9)	0.0835 (5)
Cl2	0.3294 (2)	0.01282 (11)	0.02840 (8)	0.0816 (5)
Cl3	0.40222 (17)	0.11568 (9)	0.14971 (9)	0.0755 (4)
O1	0.2031 (5)	−0.0615 (2)	0.1326 (2)	0.0663 (10)
O2	0.1059 (4)	0.04555 (17)	0.16902 (15)	0.0444 (7)
N2	−0.1503 (4)	0.12325 (18)	0.19207 (16)	0.0366 (7)
N1	0.1589 (4)	−0.05134 (18)	0.30435 (17)	0.0369 (7)
C1	0.2501 (5)	0.0635 (3)	0.0878 (2)	0.0467 (9)
C3B	−0.3058 (6)	0.2490 (3)	0.1124 (3)	0.0587 (12)
H3BA	−0.3558	0.2915	0.0857	0.070*
C2A	0.2185 (6)	−0.1699 (3)	0.3717 (3)	0.0556 (11)
H2AA	0.1850	−0.2112	0.3946	0.067*
C3A	0.3683 (6)	−0.1660 (3)	0.3713 (3)	0.0603 (12)
H3AA	0.4381	−0.2046	0.3936	0.072*
C2	0.1764 (4)	0.0082 (3)	0.1343 (2)	0.0406 (8)
C4B	−0.2629 (6)	0.2506 (3)	0.1859 (3)	0.0565 (12)
H4BA	−0.2852	0.2940	0.2101	0.068*
C4A	0.4137 (5)	−0.1035 (3)	0.3372 (3)	0.0575 (12)
H4AA	0.5147	−0.0992	0.3360	0.069*
C2B	−0.2737 (6)	0.1829 (3)	0.0785 (3)	0.0565 (11)
H2BA	−0.3042	0.1796	0.0284	0.068*
C5B	−0.1861 (5)	0.1875 (3)	0.2240 (2)	0.0458 (9)
H5BA	−0.1577	0.1894	0.2741	0.055*
C5A	0.3063 (5)	−0.0477 (3)	0.3048 (3)	0.0482 (10)
H5AA	0.3376	−0.0055	0.2823	0.058*
C1B	−0.1961 (5)	0.1222 (3)	0.1197 (2)	0.0445 (9)
H1BA	−0.1742	0.0781	0.0963	0.053*
C1A	0.1178 (5)	−0.1121 (2)	0.3380 (2)	0.0452 (9)
H1AA	0.0162	−0.1155	0.3386	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.0382 (4)	0.0279 (3)	0.0332 (3)	0.000	0.0136 (3)	0.000
Cl1	0.0853 (10)	0.0995 (12)	0.0730 (9)	0.0308 (9)	0.0347 (8)	0.0410 (8)
Cl2	0.0984 (11)	0.0965 (11)	0.0680 (8)	0.0099 (9)	0.0529 (8)	−0.0121 (8)
Cl3	0.0637 (8)	0.0730 (9)	0.0956 (11)	−0.0224 (7)	0.0323 (7)	−0.0145 (8)
O1	0.070 (2)	0.0427 (17)	0.100 (3)	−0.0004 (16)	0.047 (2)	−0.0027 (18)
O2	0.0524 (16)	0.0448 (16)	0.0427 (15)	0.0042 (13)	0.0245 (13)	0.0029 (12)
N2	0.0428 (17)	0.0319 (15)	0.0361 (15)	0.0023 (13)	0.0130 (13)	0.0004 (12)
N1	0.0396 (16)	0.0324 (15)	0.0386 (16)	0.0006 (12)	0.0114 (13)	0.0020 (12)
C1	0.051 (2)	0.050 (2)	0.045 (2)	0.0052 (19)	0.0234 (18)	0.0020 (18)
C3B	0.060 (3)	0.046 (2)	0.067 (3)	0.009 (2)	0.014 (2)	0.015 (2)
C2A	0.067 (3)	0.045 (2)	0.057 (3)	0.009 (2)	0.020 (2)	0.011 (2)
C3A	0.059 (3)	0.057 (3)	0.059 (3)	0.018 (2)	0.008 (2)	0.006 (2)
C2	0.0380 (19)	0.044 (2)	0.042 (2)	−0.0003 (16)	0.0146 (16)	0.0001 (16)
C4B	0.066 (3)	0.036 (2)	0.068 (3)	0.011 (2)	0.020 (2)	−0.002 (2)
C4A	0.038 (2)	0.064 (3)	0.067 (3)	0.003 (2)	0.010 (2)	0.003 (2)
C2B	0.057 (3)	0.066 (3)	0.044 (2)	0.007 (2)	0.0107 (19)	0.009 (2)
C5B	0.051 (2)	0.041 (2)	0.047 (2)	0.0073 (18)	0.0161 (18)	−0.0020 (17)
C5A	0.040 (2)	0.049 (2)	0.055 (2)	−0.0046 (17)	0.0125 (18)	0.0059 (19)
C1B	0.053 (2)	0.043 (2)	0.0371 (19)	0.0042 (18)	0.0130 (17)	−0.0007 (16)
C1A	0.047 (2)	0.040 (2)	0.052 (2)	0.0021 (17)	0.0204 (18)	0.0031 (18)

Geometric parameters (Å, º) top

Ni—O2	2.076 (3)	C3B—C2B	1.379 (7)
Ni—O2ⁱ	2.076 (3)	C3B—H3BA	0.9300
Ni—N1ⁱ	2.112 (3)	C2A—C3A	1.368 (8)
Ni—N1	2.112 (3)	C2A—C1A	1.377 (6)
Ni—N2ⁱ	2.131 (3)	C2A—H2AA	0.9300
Ni—N2	2.131 (3)	C3A—C4A	1.381 (8)
Cl1—C1	1.773 (5)	C3A—H3AA	0.9300
Cl2—C1	1.754 (4)	C4B—C5B	1.377 (6)
Cl3—C1	1.784 (5)	C4B—H4BA	0.9300
O1—C2	1.217 (5)	C4A—C5A	1.378 (7)
O2—C2	1.234 (5)	C4A—H4AA	0.9300
N2—C1B	1.341 (5)	C2B—C1B	1.373 (6)
N2—C5B	1.346 (5)	C2B—H2BA	0.9300
N1—C1A	1.335 (5)	C5B—H5BA	0.9300
N1—C5A	1.342 (5)	C5A—H5AA	0.9300
C1—C2	1.585 (6)	C1B—H1BA	0.9300
C3B—C4B	1.362 (8)	C1A—H1AA	0.9300

O2—Ni—O2ⁱ	169.48 (17)	C3A—C2A—C1A	119.3 (5)
O2—Ni—N1ⁱ	95.06 (13)	C3A—C2A—H2AA	120.3
O2ⁱ—Ni—N1ⁱ	92.23 (12)	C1A—C2A—H2AA	120.3
O2—Ni—N1	92.23 (12)	C2A—C3A—C4A	118.6 (4)
O2ⁱ—Ni—N1	95.06 (13)	C2A—C3A—H3AA	120.7
N1ⁱ—Ni—N1	92.18 (18)	C4A—C3A—H3AA	120.7
O2—Ni—N2ⁱ	87.95 (12)	O1—C2—O2	131.3 (4)
O2ⁱ—Ni—N2ⁱ	84.56 (12)	O1—C2—C1	116.6 (4)
N1ⁱ—Ni—N2ⁱ	176.54 (12)	O2—C2—C1	112.1 (4)
N1—Ni—N2ⁱ	89.39 (13)	C3B—C4B—C5B	119.4 (4)
O2—Ni—N2	84.56 (12)	C3B—C4B—H4BA	120.3
O2ⁱ—Ni—N2	87.95 (12)	C5B—C4B—H4BA	120.3
N1ⁱ—Ni—N2	89.39 (13)	C5A—C4A—C3A	118.7 (4)
N1—Ni—N2	176.54 (12)	C5A—C4A—H4AA	120.6
N2ⁱ—Ni—N2	89.20 (17)	C3A—C4A—H4AA	120.6
C2—O2—Ni	142.6 (3)	C1B—C2B—C3B	119.0 (4)
C1B—N2—C5B	116.7 (3)	C1B—C2B—H2BA	120.5
C1B—N2—Ni	119.8 (3)	C3B—C2B—H2BA	120.5
C5B—N2—Ni	122.9 (3)	N2—C5B—C4B	123.0 (4)
C1A—N1—C5A	117.1 (4)	N2—C5B—H5BA	118.5
C1A—N1—Ni	122.2 (3)	C4B—C5B—H5BA	118.5
C5A—N1—Ni	120.7 (3)	N1—C5A—C4A	123.2 (4)
C2—C1—Cl2	113.7 (3)	N1—C5A—H5AA	118.4
C2—C1—Cl1	110.6 (3)	C4A—C5A—H5AA	118.4
Cl2—C1—Cl1	109.7 (2)	N2—C1B—C2B	123.3 (4)
C2—C1—Cl3	106.8 (3)	N2—C1B—H1BA	118.4
Cl2—C1—Cl3	107.5 (2)	C2B—C1B—H1BA	118.4
Cl1—C1—Cl3	108.2 (3)	N1—C1A—C2A	123.2 (4)
C4B—C3B—C2B	118.6 (4)	N1—C1A—H1AA	118.4
C4B—C3B—H3BA	120.7	C2A—C1A—H1AA	118.4
C2B—C3B—H3BA	120.7

O2ⁱ—Ni—O2—C2	167.2 (5)	Ni—O2—C2—C1	−169.6 (3)
N1ⁱ—Ni—O2—C2	−59.1 (5)	Cl2—C1—C2—O1	11.1 (5)
N1—Ni—O2—C2	33.3 (5)	Cl1—C1—C2—O1	135.1 (4)
N2ⁱ—Ni—O2—C2	122.6 (5)	Cl3—C1—C2—O1	−107.3 (4)
N2—Ni—O2—C2	−148.0 (5)	Cl2—C1—C2—O2	−171.9 (3)
O2—Ni—N2—C1B	39.1 (3)	Cl1—C1—C2—O2	−47.9 (4)
O2ⁱ—Ni—N2—C1B	−148.3 (3)	Cl3—C1—C2—O2	69.7 (4)
N1ⁱ—Ni—N2—C1B	−56.0 (3)	C2B—C3B—C4B—C5B	1.4 (8)
N2ⁱ—Ni—N2—C1B	127.1 (3)	C2A—C3A—C4A—C5A	0.0 (8)
O2—Ni—N2—C5B	−131.3 (3)	C4B—C3B—C2B—C1B	−1.8 (8)
O2ⁱ—Ni—N2—C5B	41.3 (3)	C1B—N2—C5B—C4B	−1.3 (6)
N1ⁱ—Ni—N2—C5B	133.5 (3)	Ni—N2—C5B—C4B	169.4 (4)
N2ⁱ—Ni—N2—C5B	−43.3 (3)	C3B—C4B—C5B—N2	0.2 (8)
O2—Ni—N1—C1A	−143.2 (3)	C1A—N1—C5A—C4A	0.9 (7)
O2ⁱ—Ni—N1—C1A	44.4 (3)	Ni—N1—C5A—C4A	−177.6 (4)
N1ⁱ—Ni—N1—C1A	−48.1 (3)	C3A—C4A—C5A—N1	−0.6 (8)
N2ⁱ—Ni—N1—C1A	128.8 (3)	C5B—N2—C1B—C2B	0.9 (6)
O2—Ni—N1—C5A	35.1 (3)	Ni—N2—C1B—C2B	−170.1 (4)
O2ⁱ—Ni—N1—C5A	−137.3 (3)	C3B—C2B—C1B—N2	0.6 (8)
N1ⁱ—Ni—N1—C5A	130.3 (4)	C5A—N1—C1A—C2A	−0.5 (6)
N2ⁱ—Ni—N1—C5A	−52.8 (3)	Ni—N1—C1A—C2A	177.9 (4)
C1A—C2A—C3A—C4A	0.3 (8)	C3A—C2A—C1A—N1	−0.1 (7)
Ni—O2—C2—O1	6.8 (8)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4AA···O1ⁱⁱ	0.93	2.55	3.442 (7)	162
C1B—H1BA···O2	0.93	2.59	2.943 (6)	103
C1A—H1AA···O1ⁱ	0.93	2.41	3.253 (7)	151

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₂Cl₃O₂)₂(C₅H₅N)₄]
M_r	699.85
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	9.1073 (18), 17.078 (3), 19.376 (6)
β (°)	106.94 (3)
V (Å³)	2882.9 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13819, 3312, 2898
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.187, 1.07
No. of reflections	3312
No. of parameters	177
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0862P)² + 12.4612P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.63, −1.04

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
C4A—H4AA···O1ⁱ	0.9300	2.5500	3.442 (7)	162.00
C1B—H1BA···O2	0.9300	2.5900	2.943 (6)	103.00
C1A—H1AA···O1ⁱⁱ	0.9300	2.4100	3.253 (7)	151.00

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x, y, −z+1/2.

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province for support (No. Y2008B30).

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