catena-Poly[[bis­(methanol-κO)bis­(pyridine-κN)nickel(II)]-μ-tetra­fluoro­terephthalato-κ2O:O′]

Zheng, C.-G.; Hong, J.-Q.; Zhang, J.; Wang, C.

doi:10.1107/S1600536808016619

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page m879

doi:10.1107/S1600536808016619

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catena-Poly[[bis(methanol-κO)bis(pyridine-κN)nickel(II)]-μ-tetrafluoroterephthalato-κ²O:O′]

Chang-Ge Zheng,^a ^* Jian-Quan Hong,^a Jie Zhang ^a and Chao Wang ^a

^aSchool of Chemical and Materials Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China
^*Correspondence e-mail: cgzheng@126.com

(Received 26 May 2008; accepted 30 May 2008; online 7 June 2008)

In the title compound, [Ni(C₈F₄O₄)(C₅H₅N)₂(CH₄O)₂]_n, the Ni^II ion is located on an inversion center and is coordinated by four O atoms [Ni—O = 2.079 (4) Å] from two tetrafluoroterephthalate ligands and two methanol molecules, and by two N atoms [Ni—N = 2.127 (4) Å] from two pyridine ligands in a distorted octahedral geometry. The Ni^II ions are connected via the tetrafluoroterephthalate anions into a one-dimensional chain running along the crystallographic [011] direction.

Related literature

For useful applications of supramolecular coordination polymers, see: Janiak (2003 ); Rao et al. (2004 ); James (2003 ); Dietzel et al. (2005 ); Zhang et al. (2007 ). For related crystal structures, see: Kim et al. (2003 ); Go et al. (2004 ); Wang et al. (2003 ); Śledź et al. (2001 ); Li et al. (2003 ); Rosi et al. (2005 ).

Experimental

Crystal data

[Ni(C₈F₄O₄)(C₅H₅N)₂(CH₄O)₂]
M_r = 517.07
Triclinic, $[P \overline 1]$
a = 7.9159 (7) Å
b = 8.8846 (8) Å
c = 9.0219 (14) Å
α = 100.442 (9)°
β = 101.559 (9)°
γ = 114.396 (6)°
V = 540.78 (11) Å³
Z = 1
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 273 (2) K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.868, T_max = 0.909
3004 measured reflections
1901 independent reflections
1210 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.168
S = 1.03
1901 reflections
151 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.92	1.74	2.581 (6)	151

Data collection: APEX2 (Bruker, 2005 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808016619/cv2417sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016619/cv2417Isup2.hkl

checkCIF report

Comment top

Supramolecular coordination polymers have attracted considerable interest recently due to their intriguing network topologies and their potential applications as gas storage systems, sensors, catalysis, ion exchange materials and magnetic materials (Janiak, 2003; Rao et al., 2004; James, 2003; Dietzel et al., 2005). Chemical modification with the organic ligand can be carried out for constructing materials of different properties. Some research work in computational study suggests that adsorption property in gas storage can be improved with electronegative atoms in the organic linkers or frameworks (Zhang et al., 2007). New topologies with favorable properties will be achieved by introducing some strong electronegative atoms (e.g. Halogen atoms) to in the aromatic ring.

The one-dimensional linear electronically neutral chains of the title nickel(II) complex, (I) (Fig. 1), crystallizes in the triclinic space group P1. The tetrafluoroterephthalate ligands are coordinated to nickel(II) ion in one monodentate pattern. In the octahedron unit, two O atoms from the tetrafluoroterephthalate ligands and two N atoms from pyridine molecules form the equatorial plane. The axial positions are occupied by O atoms from two methanol molecules with a O—Ni—O angle of 180.0 (3)°. The equatorial plane and pyridyl ring form a dihedral angle of 15.2 (1)°. The Ni—O bond lengths are 2.079 (3) and 2.079 (4) Å and agree well with the reported values in related structures (Kim et al., 2003; Go et al., 2004). Both of the Ni—N bond lengths are 2.127 (4) Å, which are comparable with reported values in the similar complexes (Wang et al., 2003; Li et al., 2003). In the aromatic ring system, the bond lengths and bond angles are slightly larger than that in reported terephthalaic acid (Śledź et al., 2001). In addition, the hydroxyl groups of methanol molecules act as donors in O—H···O hydrogen bonds (Table 1).

Related literature top

For useful applications of supramolecular coordination polymers, see: Janiak (2003); Rao et al. (2004); James (2003); Dietzel et al. (2005); Zhang et al. (2007). For related crystal structures, see: Kim et al. (2003); Go et al. (2004); Wang et al. (2003); Śledź et al. (2001); Li et al. (2003); Rosi et al. (2005).

Experimental top

All the reagents and solvents employed were commercially available, and tetrafluoroterephthalaic acid was purified by recrystallization. The title compound was prepared according to the literature procedure of Rosi et al. (2005).

Tetrafluoroterephthalaic acid (0.0714 g, 0.30 mmol) and Ni(NO₃)₂.6H₂O (0.0436 g, 0.15 mmol) were placed in a small vial and dissolved in a mixture of methanol (3 ml) and acetonitrile (3 ml) at room temperature. The vial was then placed in a larger vial containing pyridine (4 ml), which was sealed and left undisturbed for 7 d at room temperature. The resulting green block-shaped crystals were collected by filtration, washed with methanol (3 ml), and air dried to give the title complex (0.06 g, 77% yield). Elemental analysis (%) calcd. for C₂₀H₁₈F₄N₂NiO₆: C, 46.45%; H, 3.51%; N, 5.42%; Found: C,46.48%; H, 3.55%; N, 5.38%.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A portion of the crystal structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids. The unlabelled atoms are related with the labelled ones by symmetry operation (-x, -y, -z). H atoms omitted for clarity.
	Fig. 2. Supplementary figure.

catena-Poly[[bis(methanol-κO)bis(pyridine- κN)nickel(II)]-µ-tetrafluoroterephthalato-κ²O:O'] top

Crystal data top

[Ni(C₈F₄O₄)(C₅H₅N)₂(CH₄O)₂]	Z = 1
M_r = 517.07	F(000) = 264
Triclinic, P1	D_x = 1.588 Mg m⁻³
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9159 (7) Å	Cell parameters from 409 reflections
b = 8.8846 (8) Å	θ = 3.7–18.2°
c = 9.0219 (14) Å	µ = 0.97 mm⁻¹
α = 100.442 (9)°	T = 273 K
β = 101.559 (9)°	Block, green
γ = 114.396 (6)°	0.15 × 0.12 × 0.10 mm
V = 540.78 (11) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	1901 independent reflections
Radiation source: fine-focus sealed tube	1210 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 25.0°, θ_min = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −9→9
T_min = 0.868, T_max = 0.909	k = −8→10
3004 measured reflections	l = −10→10

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.065	w = 1/[σ^2^(F_o^2^) + (0.076P)^2^ + 0.2195P], P = (F_o^2^ + 2F_c^2^)/3
wR(F²) = 0.168	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.67 e Å⁻³
1901 reflections	Δρ_min = −0.47 e Å⁻³
151 parameters

Crystal data top

[Ni(C₈F₄O₄)(C₅H₅N)₂(CH₄O)₂]	γ = 114.396 (6)°
M_r = 517.07	V = 540.78 (11) Å³
Triclinic, P1	Z = 1
a = 7.9159 (7) Å	Mo Kα radiation
b = 8.8846 (8) Å	µ = 0.97 mm⁻¹
c = 9.0219 (14) Å	T = 273 K
α = 100.442 (9)°	0.15 × 0.12 × 0.10 mm
β = 101.559 (9)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1901 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	1210 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.909	R_int = 0.045
3004 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	2 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.04	Δρ_max = 0.67 e Å⁻³
1901 reflections	Δρ_min = −0.47 e Å⁻³
151 parameters

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
Ni1	0.0000	0.0000	0.0000	0.0463 (4)
O1	−0.0204 (5)	0.1748 (4)	0.1738 (4)	0.0514 (10)
O2	0.2732 (7)	0.2924 (6)	0.3536 (5)	0.0893 (16)
O3	0.2791 (6)	0.0643 (5)	0.1351 (4)	0.0642 (12)
H3	0.2848	0.1228	0.2320	0.096*
N1	0.1405 (7)	0.2043 (5)	−0.0943 (5)	0.0495 (12)
F1	0.2568 (6)	0.6330 (4)	0.3438 (4)	0.0798 (12)
F2	−0.1649 (6)	0.1587 (4)	0.4752 (4)	0.0770 (11)
C1	0.1084 (10)	0.2749 (7)	0.3031 (7)	0.0525 (14)
C2	0.0498 (8)	0.3903 (7)	0.4030 (6)	0.0476 (13)
C3	−0.0823 (9)	0.3286 (7)	0.4841 (6)	0.0523 (14)
C4	0.1304 (8)	0.5655 (7)	0.4223 (6)	0.0538 (15)
C5	0.2384 (9)	0.1849 (8)	−0.1928 (7)	0.0636 (16)
H5	0.2395	0.0793	−0.2204	0.076*
C6	0.3374 (10)	0.3084 (10)	−0.2565 (8)	0.0781 (19)
H6	0.4006	0.2858	−0.3274	0.094*
C7	0.3426 (10)	0.4657 (10)	−0.2148 (8)	0.078 (2)
H7	0.4120	0.5537	−0.2543	0.093*
C8	0.2427 (11)	0.4911 (9)	−0.1129 (8)	0.079 (2)
H8	0.2415	0.5964	−0.0830	0.095*
C9	0.1441 (10)	0.3574 (8)	−0.0557 (7)	0.0643 (16)
H9	0.0767	0.3754	0.0133	0.077*
C10	0.3668 (15)	−0.0333 (11)	0.1774 (13)	0.148 (5)
H10A	0.3276	−0.0734	0.2628	0.222*
H10B	0.5059	0.0361	0.2107	0.222*
H10C	0.3283	−0.1308	0.0882	0.222*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0591 (8)	0.0449 (6)	0.0396 (6)	0.0293 (5)	0.0189 (5)	0.0065 (4)
O1	0.066 (3)	0.050 (2)	0.040 (2)	0.033 (2)	0.018 (2)	0.0029 (18)
O2	0.078 (3)	0.108 (4)	0.063 (3)	0.056 (3)	0.004 (3)	−0.029 (3)
O3	0.069 (3)	0.074 (3)	0.051 (2)	0.044 (2)	0.017 (2)	0.000 (2)
N1	0.056 (3)	0.049 (3)	0.046 (3)	0.026 (2)	0.018 (2)	0.012 (2)
F1	0.103 (3)	0.071 (2)	0.083 (3)	0.040 (2)	0.064 (2)	0.0212 (19)
F2	0.102 (3)	0.051 (2)	0.086 (3)	0.035 (2)	0.052 (2)	0.0126 (18)
C1	0.065 (4)	0.053 (3)	0.041 (3)	0.030 (3)	0.022 (3)	0.005 (3)
C2	0.054 (3)	0.047 (3)	0.038 (3)	0.025 (3)	0.015 (3)	−0.002 (2)
C3	0.064 (4)	0.044 (3)	0.046 (3)	0.027 (3)	0.019 (3)	0.003 (2)
C4	0.062 (4)	0.062 (4)	0.043 (3)	0.031 (3)	0.027 (3)	0.009 (3)
C5	0.076 (4)	0.066 (4)	0.063 (4)	0.039 (3)	0.036 (3)	0.022 (3)
C6	0.072 (4)	0.089 (5)	0.081 (4)	0.032 (4)	0.037 (4)	0.038 (4)
C7	0.067 (4)	0.077 (4)	0.074 (4)	0.014 (4)	0.016 (4)	0.039 (4)
C8	0.097 (5)	0.055 (4)	0.077 (4)	0.031 (4)	0.018 (4)	0.024 (3)
C9	0.086 (4)	0.056 (3)	0.058 (3)	0.036 (3)	0.029 (3)	0.017 (3)
C10	0.141 (8)	0.102 (6)	0.174 (10)	0.092 (7)	−0.036 (7)	−0.014 (6)

Geometric parameters (Å, º) top

Ni1—O3	2.079 (4)	C2—C3	1.381 (7)
Ni1—O3ⁱ	2.079 (4)	C3—C4ⁱⁱ	1.371 (7)
Ni1—O1ⁱ	2.079 (3)	C4—C3ⁱⁱ	1.371 (7)
Ni1—O1	2.079 (3)	C5—C6	1.359 (8)
Ni1—N1ⁱ	2.127 (4)	C5—H5	0.9300
Ni1—N1	2.127 (4)	C6—C7	1.361 (9)
O1—C1	1.261 (6)	C6—H6	0.9300
O2—C1	1.226 (7)	C7—C8	1.373 (10)
O3—C10	1.375 (8)	C7—H7	0.9300
O3—H3	0.9147	C8—C9	1.379 (9)
N1—C5	1.323 (7)	C8—H8	0.9300
N1—C9	1.329 (7)	C9—H9	0.9300
F1—C4	1.343 (6)	C10—H10A	0.9600
F2—C3	1.354 (6)	C10—H10B	0.9600
C1—C2	1.518 (7)	C10—H10C	0.9600
C2—C4	1.377 (7)

O3—Ni1—O3ⁱ	180.0 (3)	F2—C3—C4ⁱⁱ	118.0 (5)
O3—Ni1—O1ⁱ	88.71 (14)	F2—C3—C2	119.6 (5)
O3ⁱ—Ni1—O1ⁱ	91.29 (14)	C4ⁱⁱ—C3—C2	122.3 (5)
O3—Ni1—O1	91.29 (14)	F1—C4—C3ⁱⁱ	119.4 (5)
O3ⁱ—Ni1—O1	88.71 (14)	F1—C4—C2	118.5 (5)
O1ⁱ—Ni1—O1	180.0 (2)	C3ⁱⁱ—C4—C2	122.1 (5)
O3—Ni1—N1ⁱ	94.29 (17)	N1—C5—C6	124.6 (6)
O3ⁱ—Ni1—N1ⁱ	85.71 (17)	N1—C5—H5	117.7
O1ⁱ—Ni1—N1ⁱ	89.23 (15)	C6—C5—H5	117.7
O1—Ni1—N1ⁱ	90.77 (15)	C5—C6—C7	119.0 (7)
O3—Ni1—N1	85.71 (17)	C5—C6—H6	120.5
O3ⁱ—Ni1—N1	94.29 (17)	C7—C6—H6	120.5
O1ⁱ—Ni1—N1	90.77 (15)	C6—C7—C8	118.2 (7)
O1—Ni1—N1	89.23 (15)	C6—C7—H7	120.9
N1ⁱ—Ni1—N1	180.00 (19)	C8—C7—H7	120.9
C1—O1—Ni1	127.3 (4)	C7—C8—C9	118.8 (6)
C10—O3—Ni1	132.9 (5)	C7—C8—H8	120.6
C10—O3—H3	101.1	C9—C8—H8	120.6
Ni1—O3—H3	101.3	N1—C9—C8	123.3 (6)
C5—N1—C9	116.1 (5)	N1—C9—H9	118.3
C5—N1—Ni1	119.8 (4)	C8—C9—H9	118.3
C9—N1—Ni1	124.0 (4)	O3—C10—H10A	109.5
O2—C1—O1	127.9 (5)	O3—C10—H10B	109.5
O2—C1—C2	117.6 (5)	H10A—C10—H10B	109.5
O1—C1—C2	114.4 (5)	O3—C10—H10C	109.5
C4—C2—C3	115.6 (5)	H10A—C10—H10C	109.5
C4—C2—C1	121.7 (5)	H10B—C10—H10C	109.5
C3—C2—C1	122.6 (5)

O3—Ni1—O1—C1	1.8 (5)	Ni1—O1—C1—C2	178.6 (3)
O3ⁱ—Ni1—O1—C1	−178.2 (5)	O2—C1—C2—C4	69.3 (8)
O1ⁱ—Ni1—O1—C1	−146 (100)	O1—C1—C2—C4	−108.6 (6)
N1ⁱ—Ni1—O1—C1	96.1 (5)	O2—C1—C2—C3	−108.6 (7)
N1—Ni1—O1—C1	−83.9 (5)	O1—C1—C2—C3	73.5 (7)
O3ⁱ—Ni1—O3—C10	142 (100)	C4—C2—C3—F2	−178.3 (5)
O1ⁱ—Ni1—O3—C10	−48.5 (8)	C1—C2—C3—F2	−0.3 (8)
O1—Ni1—O3—C10	131.5 (8)	C4—C2—C3—C4ⁱⁱ	0.1 (9)
N1ⁱ—Ni1—O3—C10	40.6 (8)	C1—C2—C3—C4ⁱⁱ	178.1 (5)
N1—Ni1—O3—C10	−139.4 (8)	C3—C2—C4—F1	−178.6 (5)
O3—Ni1—N1—C5	72.0 (4)	C1—C2—C4—F1	3.4 (8)
O3ⁱ—Ni1—N1—C5	−108.0 (4)	C3—C2—C4—C3ⁱⁱ	−0.1 (9)
O1ⁱ—Ni1—N1—C5	−16.7 (4)	C1—C2—C4—C3ⁱⁱ	−178.2 (5)
O1—Ni1—N1—C5	163.3 (4)	C9—N1—C5—C6	−0.8 (9)
N1ⁱ—Ni1—N1—C5	−169 (100)	Ni1—N1—C5—C6	−178.2 (5)
O3—Ni1—N1—C9	−105.2 (5)	N1—C5—C6—C7	1.8 (10)
O3ⁱ—Ni1—N1—C9	74.8 (5)	C5—C6—C7—C8	−1.7 (10)
O1ⁱ—Ni1—N1—C9	166.2 (5)	C6—C7—C8—C9	0.9 (10)
O1—Ni1—N1—C9	−13.8 (5)	C5—N1—C9—C8	0.0 (9)
N1ⁱ—Ni1—N1—C9	14 (100)	Ni1—N1—C9—C8	177.2 (5)
Ni1—O1—C1—O2	0.9 (9)	C7—C8—C9—N1	0.0 (10)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.92	1.74	2.581 (6)	151

Experimental details

Crystal data
Chemical formula	[Ni(C₈F₄O₄)(C₅H₅N)₂(CH₄O)₂]
M_r	517.07
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.9159 (7), 8.8846 (8), 9.0219 (14)
α, β, γ (°)	100.442 (9), 101.559 (9), 114.396 (6)
V (Å³)	540.78 (11)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.868, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	3004, 1901, 1210
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.168, 1.04
No. of reflections	1901
No. of parameters	151
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.47

Computer programs: APEX2 (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.915	1.743	2.581 (6)	150.97

Acknowledgements

This work was supported by the Center of Analysis and Testing of Jiangnan University, and the Research Institute of Elemento-organic Chemistry of Taishan College.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
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