metal-organic compounds
catena-Poly[[diaquabis(4-formylbenzoato-κO1)nickel(II)]-μ-pyrazine-κ2N:N′]
aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, bAksaray University, Department of Physics, 68100, Aksaray, Turkey, cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr
In the title polymeric compound, [Ni(C8H5O3)2(C4H4N2)(H2O)2]n, the NiII atom is located on a twofold rotation axis and has a slightly distorted octahedral coordination sphere. In the equatorial plane, it is coordinated by two carboxylate O atoms of two symmetry-related monodentate formylbenzoate anions and by two N atoms of the bridging pyrazine ligand, which is bisected by the twofold rotation axis. The axial positions are occupied by two O atoms of the coordinating water molecules. In the formylbenzoate anion, the carboxylate group is twisted away from the attached benzene ring by 7.0 (6)°, while the benzene and pyrazine rings are oriented at a dihedral angle of 66.2 (3)°. The pyrazine ligands bridge the NiII cations, forming polymeric chains running along the b-axis direction. Intramolecular O—H⋯O hydrogen bonds link the water ligands to the carboxylate O atoms. In the crystal, water–water O—H⋯O hydrogen bonds link adjacent chains into layers parallel to the bc plane. Pyrazine–formyl C—H⋯O hydrogen bonds link the layers, forming a three-dimensional network. There are also weak C—H⋯π interactions present. The title compound is isotypic with the copper(II) complex [Çelik et al. (2014a). Acta Cryst. E70, m4–m5].
CCDC reference: 982792
Related literature
For the structural functions and coordination relationships of the arylcarboxylate ion in transition-metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981); Shnulin et al. (1981). For applications of transition-metal complexes with biochemical molecules in biological systems, see: Antolini et al. (1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes, see: Chen & Chen (2002); Amiraslanov et al. (1979); Hauptmann et al. (2000). For the isotypic copper(II) complex, see: Çelik et al. (2014a). For other related structures involving 4-formylbenzoate, see: Çelik et al. (2014b); Hökelek et al. (2009). For standard bond lengths, see: Allen et al. (1987).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2012); cell SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 982792
10.1107/S160053681400155X/su2690sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400155X/su2690Isup2.hkl
The title compound was prepared by the reaction of NiSO4.6H2O (1.31 g, 5 mmol) in H2O (70 ml) and pyrazine (0.40 g, 5 mmol) in H2O (30 ml) with sodium 4-formylbenzoate (1.72 g, 10 mmol) in H2O (100 ml) at room temperature. The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving blue prismatic crystals.
Atoms H41 and H42 (for H2O) were located in a difference Fourier map and were refined with distance restraints: O-H = 0.82 (2) Å. The C-bound H-atoms were positioned geometrically with C—H = 0.93 Å for aromatic H-atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). Both the highest residual electron density and the deepest hole were found 0.88 Å from atom Ni1.
The structural functions and coordination relationships of the arylcarboxylate ion in transition metal complexes of benzoic acid derivatives change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the medium of the synthesis (Nadzhafov et al., 1981; Shnulin et al., 1981). Transition metal complexes with biochemically active ligands frequently show interesting physical and/or chemical properties, as a result they may find applications in biological systems (Antolini et al., 1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes (Chen & Chen, 2002; Amiraslanov et al., 1979; Hauptmann et al., 2000). The title compound, which is isotructural with the copper(II) complex (Çelik et al., 2014a) was synthesized and its
is reported on herein.The
of the title compound contains half a NiII ion, one formylbenzoate (FB) anion, one water molecule and half of a pyrazine molecule. Atoms Ni1, and N1 and N2 of the pyrazine ligand, are located on a two-fold rotation axis (Fig. 1). The pyrazine ligands bridge adjacent NiII ions forming polymeric chains running along the b-axis direction (Fig. 2). The distances between the symmetry related NiII ions [Ni1···Ni1i; symmetry code: (i) x, y + 1, z] is 6.992 (3) Å.In the equatorial plane of the NiII, coordination sphere is composed of two carboxylate O atoms (O2 and O2ii; symmetry code: (ii) - x, y, - z + 1/2) of two symmetry related monodentate formylbenzoate anions and two N atoms (N1 and N2) of the bridging pyrazine ligand, which is bisected by the two-fold rotation axis. The axial positions are occupied by two O atoms (O4 and O4ii) of the coordinated water molecules.
The near equality of the C1—O1 [1.250 (7) Å] and C1—O2 [1.260 (6) Å] bonds in the carboxylate group indicate delocalized bonding arrangement, rather than localized single and double bonds. The Ni—N bond lengths are 2.108 (6) and 2.112 (6) Å, while the Ni—O bond lengths are 2.047 (4) Å (for benzoate oxygen) and 2.107 (4) Å (for water oxygen) close to standard values (Allen et al., 1987). The Ni1 atom is displaced out of the mean-plane of the carboxylate group (O1/C1/O2) by 0.0658 (8) Å. The dihedral angle between the planar carboxylate group and the adjacent benzene ring (C2—C7) is 7.0 (6)°, while the benzene and pyrazine rings are oriented at a dihedral angle of 66.2 (3) °. Strong intramolecular O—H···O hydrogen bonds (Table 1) link the water molecules to the carboxylate oxygens.
In the crystal, O-Hwater···Owater hydrogen bonds link adjacent chains into layers parallel to the bc plane (Table 1). C—Hpyrazine···Oformyl hydrogen bonds (Table 1) link the layers to form a three-dimensional network. There are also weak C—H···π interactions present (Table 1).
For the structural functions and coordination relationships of the arylcarboxylate ion in transition-metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981); Shnulin et al. (1981). For applications of transition-metal complexes with biochemical molecules in biological systems, see: Antolini et al. (1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes, see: Chen & Chen (2002); Amiraslanov et al. (1979); Hauptmann et al. (2000). For the isotypic copper(II) complex, see: Çelik et al. (2014a). For other related structures involving 4-formylbenzoate, see: Çelik et al. (2014b); Hökelek et al. (2009). For standard bond lengths, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. A view of the coordination geometry around the NiII atom of the title molecule, with the atom-labelling. Displacement ellipsoids are drawn at the 50% probability level. The two-fold rotation axis bisects atoms Ni1, N1 and N2. | |
Fig. 2. A partial view along the c axis of the crystal packing of the title compound. Hydrogen atoms have been omitted for clarity. |
[Ni(C8H5O3)2(C4H4N2)(H2O)2] | F(000) = 976 |
Mr = 473.07 | Dx = 1.652 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5837 reflections |
a = 22.1032 (5) Å | θ = 3.1–28.3° |
b = 6.9925 (2) Å | µ = 1.08 mm−1 |
c = 12.3366 (3) Å | T = 296 K |
β = 94.160 (3)° | Prism, blue |
V = 1901.68 (8) Å3 | 0.48 × 0.23 × 0.14 mm |
Z = 4 |
Bruker SMART BREEZE CCD diffractometer | 1717 independent reflections |
Radiation source: fine-focus sealed tube | 1554 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
φ and ω scans | θmax = 25.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −26→26 |
Tmin = 0.743, Tmax = 0.860 | k = −8→8 |
9913 measured reflections | l = −14→12 |
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)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.209 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | w = 1/[σ2(Fo2) + (0.1238P)2 + 9.9995P] where P = (Fo2 + 2Fc2)/3 |
1717 reflections | (Δ/σ)max < 0.001 |
150 parameters | Δρmax = 2.49 e Å−3 |
2 restraints | Δρmin = −1.05 e Å−3 |
[Ni(C8H5O3)2(C4H4N2)(H2O)2] | V = 1901.68 (8) Å3 |
Mr = 473.07 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 22.1032 (5) Å | µ = 1.08 mm−1 |
b = 6.9925 (2) Å | T = 296 K |
c = 12.3366 (3) Å | 0.48 × 0.23 × 0.14 mm |
β = 94.160 (3)° |
Bruker SMART BREEZE CCD diffractometer | 1717 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 1554 reflections with I > 2σ(I) |
Tmin = 0.743, Tmax = 0.860 | Rint = 0.070 |
9913 measured reflections |
R[F2 > 2σ(F2)] = 0.079 | 2 restraints |
wR(F2) = 0.209 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | Δρmax = 2.49 e Å−3 |
1717 reflections | Δρmin = −1.05 e Å−3 |
150 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
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 > 2sigma(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 | 0.00000 | 0.44790 (12) | 0.25000 | 0.0222 (3) | |
O1 | 0.13672 (19) | 0.3246 (7) | 0.3338 (3) | 0.0435 (14) | |
O2 | 0.08397 (17) | 0.4511 (5) | 0.1900 (3) | 0.0294 (11) | |
O3 | 0.3999 (2) | 0.3724 (9) | 0.0460 (4) | 0.0614 (19) | |
O4 | 0.0372 (2) | 0.4332 (6) | 0.4119 (3) | 0.0342 (12) | |
N1 | 0.00000 | 0.1464 (8) | 0.25000 | 0.0242 (17) | |
N2 | 0.00000 | 0.7500 (8) | 0.25000 | 0.0260 (19) | |
C1 | 0.1321 (2) | 0.3907 (7) | 0.2394 (5) | 0.0277 (16) | |
C2 | 0.1890 (2) | 0.3983 (7) | 0.1787 (5) | 0.0284 (16) | |
C3 | 0.1889 (3) | 0.4908 (8) | 0.0787 (5) | 0.0300 (17) | |
C4 | 0.2420 (3) | 0.5042 (9) | 0.0271 (5) | 0.0320 (17) | |
C5 | 0.2955 (3) | 0.4294 (8) | 0.0736 (5) | 0.0339 (17) | |
C6 | 0.2958 (3) | 0.3342 (8) | 0.1733 (5) | 0.0338 (17) | |
C7 | 0.2424 (2) | 0.3196 (8) | 0.2243 (5) | 0.0290 (17) | |
C8 | 0.3520 (3) | 0.4471 (10) | 0.0178 (6) | 0.045 (2) | |
C9 | 0.0252 (3) | 0.0463 (7) | 0.1723 (5) | 0.0290 (17) | |
C10 | 0.0250 (2) | 0.8494 (7) | 0.1733 (4) | 0.0280 (17) | |
H3 | 0.15320 | 0.54320 | 0.04700 | 0.0360* | |
H4 | 0.24170 | 0.56450 | −0.04010 | 0.0380* | |
H6 | 0.33140 | 0.28130 | 0.20480 | 0.0410* | |
H7 | 0.24240 | 0.25590 | 0.29040 | 0.0350* | |
H8 | 0.35070 | 0.52240 | −0.04450 | 0.0540* | |
H9 | 0.04310 | 0.11080 | 0.11700 | 0.0350* | |
H10 | 0.04300 | 0.78400 | 0.11840 | 0.0340* | |
H41 | 0.040 (4) | 0.545 (5) | 0.430 (7) | 0.06 (3)* | |
H42 | 0.0721 (18) | 0.396 (13) | 0.407 (7) | 0.07 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0321 (6) | 0.0093 (5) | 0.0253 (6) | 0.0000 | 0.0022 (4) | 0.0000 |
O1 | 0.046 (2) | 0.049 (3) | 0.036 (2) | 0.008 (2) | 0.0059 (18) | 0.012 (2) |
O2 | 0.032 (2) | 0.0188 (19) | 0.038 (2) | 0.0020 (14) | 0.0065 (16) | 0.0009 (16) |
O3 | 0.045 (3) | 0.085 (4) | 0.055 (3) | 0.001 (3) | 0.010 (2) | −0.006 (3) |
O4 | 0.047 (2) | 0.031 (2) | 0.024 (2) | 0.0063 (19) | −0.0012 (17) | −0.0034 (17) |
N1 | 0.036 (3) | 0.011 (3) | 0.026 (3) | 0.0000 | 0.005 (2) | 0.0000 |
N2 | 0.034 (3) | 0.006 (3) | 0.038 (4) | 0.0000 | 0.003 (3) | 0.0000 |
C1 | 0.039 (3) | 0.012 (2) | 0.032 (3) | −0.002 (2) | 0.002 (2) | 0.000 (2) |
C2 | 0.040 (3) | 0.013 (2) | 0.032 (3) | −0.002 (2) | 0.002 (2) | −0.004 (2) |
C3 | 0.036 (3) | 0.022 (3) | 0.031 (3) | 0.000 (2) | −0.004 (2) | −0.002 (2) |
C4 | 0.047 (3) | 0.023 (3) | 0.026 (3) | −0.006 (2) | 0.003 (2) | 0.000 (2) |
C5 | 0.040 (3) | 0.026 (3) | 0.036 (3) | −0.005 (2) | 0.004 (2) | −0.007 (2) |
C6 | 0.036 (3) | 0.027 (3) | 0.038 (3) | 0.005 (2) | 0.001 (2) | −0.002 (2) |
C7 | 0.039 (3) | 0.021 (3) | 0.027 (3) | 0.005 (2) | 0.003 (2) | 0.002 (2) |
C8 | 0.050 (4) | 0.044 (4) | 0.043 (4) | −0.007 (3) | 0.008 (3) | −0.002 (3) |
C9 | 0.045 (3) | 0.017 (3) | 0.026 (3) | −0.002 (2) | 0.009 (2) | 0.002 (2) |
C10 | 0.041 (3) | 0.016 (3) | 0.028 (3) | 0.000 (2) | 0.010 (2) | −0.004 (2) |
Ni1—O2 | 2.048 (4) | C2—C3 | 1.393 (8) |
Ni1—O4 | 2.107 (4) | C2—C7 | 1.384 (7) |
Ni1—N1 | 2.108 (6) | C3—C4 | 1.378 (9) |
Ni1—N2 | 2.112 (6) | C4—C5 | 1.379 (9) |
Ni1—O2i | 2.048 (4) | C5—C6 | 1.398 (9) |
Ni1—O4i | 2.107 (4) | C5—C8 | 1.474 (9) |
O1—C1 | 1.250 (7) | C6—C7 | 1.381 (8) |
O2—C1 | 1.260 (6) | C9—C10ii | 1.377 (7) |
O3—C8 | 1.209 (8) | C3—H3 | 0.9300 |
O4—H42 | 0.82 (5) | C4—H4 | 0.9300 |
O4—H41 | 0.81 (4) | C6—H6 | 0.9300 |
N1—C9i | 1.340 (7) | C7—H7 | 0.9300 |
N1—C9 | 1.340 (7) | C8—H8 | 0.9300 |
N2—C10 | 1.327 (6) | C9—H9 | 0.9300 |
N2—C10i | 1.327 (6) | C10—H10 | 0.9300 |
C1—C2 | 1.511 (7) | ||
O2—Ni1—O4 | 92.38 (16) | C3—C2—C7 | 119.4 (5) |
O2—Ni1—N1 | 90.63 (10) | C1—C2—C7 | 120.0 (5) |
O2—Ni1—N2 | 89.37 (10) | C1—C2—C3 | 120.5 (5) |
O2—Ni1—O2i | 178.75 (15) | C2—C3—C4 | 119.6 (6) |
O2—Ni1—O4i | 87.68 (16) | C3—C4—C5 | 121.0 (6) |
O4—Ni1—N1 | 87.20 (12) | C4—C5—C6 | 119.7 (6) |
O4—Ni1—N2 | 92.80 (12) | C4—C5—C8 | 120.2 (6) |
O2i—Ni1—O4 | 87.68 (16) | C6—C5—C8 | 120.0 (6) |
O4—Ni1—O4i | 174.41 (17) | C5—C6—C7 | 119.1 (6) |
N1—Ni1—N2 | 180.00 (1) | C2—C7—C6 | 121.2 (6) |
O2i—Ni1—N1 | 90.63 (10) | O3—C8—C5 | 125.7 (7) |
O4i—Ni1—N1 | 87.20 (12) | N1—C9—C10ii | 120.9 (5) |
O2i—Ni1—N2 | 89.37 (10) | N2—C10—C9iii | 122.2 (5) |
O4i—Ni1—N2 | 92.80 (12) | C2—C3—H3 | 120.00 |
O2i—Ni1—O4i | 92.38 (16) | C4—C3—H3 | 120.00 |
Ni1—O2—C1 | 125.3 (4) | C3—C4—H4 | 119.00 |
Ni1—O4—H41 | 103 (6) | C5—C4—H4 | 120.00 |
Ni1—O4—H42 | 105 (6) | C5—C6—H6 | 120.00 |
H41—O4—H42 | 106 (9) | C7—C6—H6 | 120.00 |
C9—N1—C9i | 117.0 (5) | C2—C7—H7 | 120.00 |
Ni1—N1—C9 | 121.5 (3) | C6—C7—H7 | 119.00 |
Ni1—N1—C9i | 121.5 (3) | O3—C8—H8 | 117.00 |
Ni1—N2—C10 | 121.6 (3) | C5—C8—H8 | 117.00 |
Ni1—N2—C10i | 121.6 (3) | N1—C9—H9 | 120.00 |
C10—N2—C10i | 116.8 (5) | C10ii—C9—H9 | 120.00 |
O1—C1—O2 | 125.7 (5) | N2—C10—H10 | 119.00 |
O2—C1—C2 | 116.9 (5) | C9iii—C10—H10 | 119.00 |
O1—C1—C2 | 117.4 (4) | ||
O4—Ni1—O2—C1 | 22.0 (4) | Ni1—N1—C9—C10ii | 179.9 (4) |
N1—Ni1—O2—C1 | −65.3 (4) | Ni1—N2—C10—C9iii | 179.9 (4) |
N2—Ni1—O2—C1 | 114.7 (4) | O1—C1—C2—C3 | −172.2 (5) |
O4i—Ni1—O2—C1 | −152.5 (4) | O1—C1—C2—C7 | 5.2 (8) |
O2—Ni1—N1—C9 | −35.6 (3) | O2—C1—C2—C3 | 8.0 (7) |
O2—Ni1—N1—C9i | 144.4 (3) | O2—C1—C2—C7 | −174.5 (5) |
O4—Ni1—N1—C9 | −128.0 (3) | C1—C2—C3—C4 | 176.9 (5) |
O4—Ni1—N1—C9i | 52.0 (3) | C7—C2—C3—C4 | −0.6 (8) |
O2i—Ni1—N1—C9 | 144.4 (3) | C1—C2—C7—C6 | −176.3 (5) |
O4i—Ni1—N1—C9 | 52.0 (3) | C3—C2—C7—C6 | 1.2 (8) |
O2—Ni1—N2—C10 | 35.5 (3) | C2—C3—C4—C5 | −0.8 (9) |
O2—Ni1—N2—C10i | −144.5 (3) | C3—C4—C5—C6 | 1.6 (9) |
O4—Ni1—N2—C10 | 127.9 (3) | C3—C4—C5—C8 | −179.3 (6) |
O4—Ni1—N2—C10i | −52.1 (3) | C4—C5—C6—C7 | −1.0 (9) |
O2i—Ni1—N2—C10 | −144.5 (3) | C8—C5—C6—C7 | 179.9 (6) |
O4i—Ni1—N2—C10 | −52.1 (3) | C4—C5—C8—O3 | −172.9 (7) |
Ni1—O2—C1—O1 | −2.3 (8) | C6—C5—C8—O3 | 6.3 (10) |
Ni1—O2—C1—C2 | 177.5 (3) | C5—C6—C7—C2 | −0.4 (9) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) x, y−1, z; (iii) x, y+1, z. |
Cg1 is the centroid of the C2–C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H42···O1 | 0.82 (5) | 1.81 (6) | 2.579 (6) | 155 (8) |
O4—H41···O3iv | 0.82 (2) | 2.65 (5) | 3.395 (8) | 152 (8) |
C9—H9···O3v | 0.93 | 2.45 | 3.311 (8) | 154 |
C7—H7···Cg1vi | 0.93 | 2.62 | 3.395 (6) | 141 |
Symmetry codes: (iv) −x+1/2, y+1/2, −z+1/2; (v) −x+1/2, −y+1/2, −z; (vi) −x+1/2, y−1/2, −z+1/2. |
Cg1 is the centroid of the C2–C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H42···O1 | 0.82 (5) | 1.81 (6) | 2.579 (6) | 155 (8) |
O4—H41···O3i | 0.82 (2) | 2.65 (5) | 3.395 (8) | 152 (8) |
C9—H9···O3ii | 0.93 | 2.45 | 3.311 (8) | 154 |
C7—H7···Cg1iii | 0.93 | 2.62 | 3.395 (6) | 141 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z; (iii) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization). This work is supported financially by Kafkas University Research Fund (grant No. 2012-FEF-12).
References
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The structural functions and coordination relationships of the arylcarboxylate ion in transition metal complexes of benzoic acid derivatives change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the medium of the synthesis (Nadzhafov et al., 1981; Shnulin et al., 1981). Transition metal complexes with biochemically active ligands frequently show interesting physical and/or chemical properties, as a result they may find applications in biological systems (Antolini et al., 1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes (Chen & Chen, 2002; Amiraslanov et al., 1979; Hauptmann et al., 2000). The title compound, which is isotructural with the copper(II) complex (Çelik et al., 2014a) was synthesized and its crystal structure is reported on herein.
The asymmetric unit of the title compound contains half a NiII ion, one formylbenzoate (FB) anion, one water molecule and half of a pyrazine molecule. Atoms Ni1, and N1 and N2 of the pyrazine ligand, are located on a two-fold rotation axis (Fig. 1). The pyrazine ligands bridge adjacent NiII ions forming polymeric chains running along the b-axis direction (Fig. 2). The distances between the symmetry related NiII ions [Ni1···Ni1i; symmetry code: (i) x, y + 1, z] is 6.992 (3) Å.
In the equatorial plane of the NiII, coordination sphere is composed of two carboxylate O atoms (O2 and O2ii; symmetry code: (ii) - x, y, - z + 1/2) of two symmetry related monodentate formylbenzoate anions and two N atoms (N1 and N2) of the bridging pyrazine ligand, which is bisected by the two-fold rotation axis. The axial positions are occupied by two O atoms (O4 and O4ii) of the coordinated water molecules.
The near equality of the C1—O1 [1.250 (7) Å] and C1—O2 [1.260 (6) Å] bonds in the carboxylate group indicate delocalized bonding arrangement, rather than localized single and double bonds. The Ni—N bond lengths are 2.108 (6) and 2.112 (6) Å, while the Ni—O bond lengths are 2.047 (4) Å (for benzoate oxygen) and 2.107 (4) Å (for water oxygen) close to standard values (Allen et al., 1987). The Ni1 atom is displaced out of the mean-plane of the carboxylate group (O1/C1/O2) by 0.0658 (8) Å. The dihedral angle between the planar carboxylate group and the adjacent benzene ring (C2—C7) is 7.0 (6)°, while the benzene and pyrazine rings are oriented at a dihedral angle of 66.2 (3) °. Strong intramolecular O—H···O hydrogen bonds (Table 1) link the water molecules to the carboxylate oxygens.
In the crystal, O-Hwater···Owater hydrogen bonds link adjacent chains into layers parallel to the bc plane (Table 1). C—Hpyrazine···Oformyl hydrogen bonds (Table 1) link the layers to form a three-dimensional network. There are also weak C—H···π interactions present (Table 1).