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metal-organic compounds
Tetraaquabis(isonicotinamide-κN1)nickel(II) bis(4-formylbenzoate) dihydrate
aDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, bDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey, cDepartment of Physics, Karabük University, 78050 Karabük, Turkey, and dDepartment of Chemistry, Kafkas University, 63100 Kars, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr
The 6H6N2O)2(H2O)4](C8H5O3)2·2H2O, contains one-half of the complex cation with the NiII atom located on an inversion center, a 4-formylbenzoate (FB) counter-anion and an uncoordinated water molecule. The four O atoms in the equatorial plane around the Ni atom form a slightly distorted square-planar arrangement and the slightly distorted octahedral coordination is completed by the two N atoms of the isonicotinamide (INA) ligands at a sligthly longer distance in the axial positions. The dihedral angle between the carboxylate group and the attached benzene ring is 8.14 (11)°, while the pyridine and benzene rings are oriented at a dihedral angle of 3.46 (6)°. In the O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. π–π Contacts between the benzene and pyridine rings [centroid–centroid distance = 3.751 (1) Å] may further stabilize the crystal structure.
of the title complex, [Ni(CRelated literature
For general background, see: Bigoli et al. (1972); Krishnamachari (1974
). For related structures, see: Hökelek et al. (2009
); Sertçelik et al. (2009
).
Experimental
Crystal data
|
Refinement
|
|
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007
); 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, 1997
); software used to prepare material for publication: WinGX (Farrugia, 1999
) and PLATON (Spek, 2009
).
Supporting information
10.1107/S1600536809032279/xu2589sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809032279/xu2589Isup2.hkl
The title compound was prepared by the reaction of NiSO4.6H2O (1.31 g, 5 mmol) in H2O (25 ml) and INA (1.22 g, 10 mmol) in H2O (40 ml) with sodium 4-formylbenzoate (1.72 g, 10 mmol) in H2O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving blue single crystals.
Atoms H51, H52, H61, H62, H71 and H72 (for H2O), H21 and H22 (for NH2) and H14 (for CH) were located in difference Fourier map and refined isotropically. The remaining 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).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).[Ni(C6H6N2O)2(H2O)4](C8H5O3)2·2H2O | Z = 1 |
Mr = 709.28 | F(000) = 370 |
Triclinic, P1 | Dx = 1.554 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4338 (1) Å | Cell parameters from 5282 reflections |
b = 6.9059 (2) Å | θ = 4.1–28.3° |
c = 18.1649 (3) Å | µ = 0.72 mm−1 |
α = 81.658 (2)° | T = 100 K |
β = 85.160 (3)° | Block, blue |
γ = 71.816 (1)° | 0.35 × 0.15 × 0.1 mm |
V = 758.01 (3) Å3 |
Bruker Kappa APEXII CCD area-detector diffractometer | 3837 independent reflections |
Radiation source: fine-focus sealed tube | 3259 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ϕ and ω scans | θmax = 28.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −8→8 |
Tmin = 0.876, Tmax = 0.928 | k = −9→9 |
14080 measured reflections | l = −24→24 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0396P)2] where P = (Fo2 + 2Fc2)/3 |
3837 reflections | (Δ/σ)max < 0.001 |
250 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
[Ni(C6H6N2O)2(H2O)4](C8H5O3)2·2H2O | γ = 71.816 (1)° |
Mr = 709.28 | V = 758.01 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 6.4338 (1) Å | Mo Kα radiation |
b = 6.9059 (2) Å | µ = 0.72 mm−1 |
c = 18.1649 (3) Å | T = 100 K |
α = 81.658 (2)° | 0.35 × 0.15 × 0.1 mm |
β = 85.160 (3)° |
Bruker Kappa APEXII CCD area-detector diffractometer | 3837 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3259 reflections with I > 2σ(I) |
Tmin = 0.876, Tmax = 0.928 | Rint = 0.067 |
14080 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.50 e Å−3 |
3837 reflections | Δρmin = −0.47 e Å−3 |
250 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.0000 | 0.0000 | 0.0000 | 0.00952 (9) | |
O1 | −0.32770 (17) | 0.69399 (18) | −0.08791 (6) | 0.0156 (2) | |
O2 | 0.02696 (17) | 0.55211 (17) | −0.11784 (6) | 0.0147 (2) | |
O3 | −0.5543 (2) | 0.7444 (2) | −0.46465 (6) | 0.0248 (3) | |
O4 | 0.62907 (18) | −0.23630 (19) | 0.31701 (6) | 0.0187 (3) | |
O5 | 0.18852 (18) | 0.19178 (18) | −0.02699 (6) | 0.0121 (2) | |
H51 | 0.228 (4) | 0.229 (4) | 0.0063 (13) | 0.050 (8)* | |
H52 | 0.124 (3) | 0.303 (3) | −0.0585 (10) | 0.027 (5)* | |
O6 | 0.23596 (19) | −0.24606 (18) | −0.04216 (6) | 0.0143 (2) | |
H61 | 0.370 (4) | −0.265 (4) | −0.0591 (12) | 0.048 (7)* | |
H62 | 0.181 (4) | −0.320 (4) | −0.0624 (12) | 0.040 (7)* | |
O7 | 0.8514 (2) | −0.1254 (2) | 0.41718 (7) | 0.0214 (3) | |
H71 | 0.771 (4) | −0.021 (4) | 0.4322 (13) | 0.055 (9)* | |
H72 | 0.775 (3) | −0.155 (3) | 0.3879 (12) | 0.037 (6)* | |
N1 | 0.1326 (2) | −0.0939 (2) | 0.10564 (7) | 0.0112 (3) | |
N2 | 0.3028 (2) | −0.1740 (2) | 0.37981 (7) | 0.0153 (3) | |
H21 | 0.166 (3) | −0.153 (3) | 0.3816 (10) | 0.024 (5)* | |
H22 | 0.369 (3) | −0.199 (3) | 0.4221 (10) | 0.021 (5)* | |
C1 | −0.1722 (2) | 0.6250 (2) | −0.13329 (8) | 0.0129 (3) | |
C2 | −0.2270 (2) | 0.6334 (2) | −0.21321 (8) | 0.0120 (3) | |
C3 | −0.4455 (2) | 0.6912 (2) | −0.23337 (8) | 0.0130 (3) | |
H3 | −0.5580 | 0.7218 | −0.1972 | 0.016* | |
C4 | −0.4939 (3) | 0.7027 (3) | −0.30658 (8) | 0.0149 (3) | |
H4 | −0.6391 | 0.7411 | −0.3198 | 0.018* | |
C5 | −0.3256 (3) | 0.6570 (3) | −0.36097 (8) | 0.0142 (3) | |
C6 | −0.1081 (3) | 0.5964 (3) | −0.34101 (8) | 0.0159 (3) | |
H6 | 0.0043 | 0.5631 | −0.3771 | 0.019* | |
C7 | −0.0597 (3) | 0.5859 (3) | −0.26751 (8) | 0.0144 (3) | |
H7 | 0.0855 | 0.5468 | −0.2543 | 0.017* | |
C8 | 0.0066 (2) | −0.0685 (2) | 0.16870 (8) | 0.0119 (3) | |
H8 | −0.1447 | −0.0268 | 0.1651 | 0.014* | |
C9 | 0.0914 (2) | −0.1014 (2) | 0.23847 (8) | 0.0126 (3) | |
H9 | −0.0017 | −0.0812 | 0.2806 | 0.015* | |
C10 | 0.3172 (2) | −0.1649 (2) | 0.24511 (8) | 0.0109 (3) | |
C11 | 0.4476 (2) | −0.1990 (3) | 0.18050 (8) | 0.0133 (3) | |
H11 | 0.5993 | −0.2465 | 0.1828 | 0.016* | |
C12 | 0.3506 (2) | −0.1620 (3) | 0.11290 (8) | 0.0139 (3) | |
H12 | 0.4406 | −0.1854 | 0.0702 | 0.017* | |
C13 | 0.4277 (3) | −0.1948 (2) | 0.31741 (8) | 0.0130 (3) | |
C14 | −0.3734 (3) | 0.6682 (3) | −0.43942 (9) | 0.0197 (4) | |
H14 | −0.245 (3) | 0.614 (3) | −0.4731 (10) | 0.021 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.00852 (14) | 0.01296 (17) | 0.00766 (14) | −0.00363 (11) | −0.00026 (10) | −0.00235 (11) |
O1 | 0.0131 (5) | 0.0221 (7) | 0.0133 (5) | −0.0060 (5) | 0.0003 (4) | −0.0068 (5) |
O2 | 0.0121 (5) | 0.0168 (6) | 0.0160 (5) | −0.0042 (5) | −0.0035 (4) | −0.0032 (5) |
O3 | 0.0253 (7) | 0.0314 (8) | 0.0150 (6) | −0.0030 (6) | −0.0067 (5) | −0.0039 (5) |
O4 | 0.0123 (6) | 0.0267 (7) | 0.0168 (5) | −0.0033 (5) | −0.0039 (4) | −0.0063 (5) |
O5 | 0.0122 (5) | 0.0151 (6) | 0.0101 (5) | −0.0055 (5) | −0.0011 (4) | −0.0017 (5) |
O6 | 0.0111 (6) | 0.0176 (6) | 0.0159 (5) | −0.0048 (5) | 0.0010 (4) | −0.0072 (5) |
O7 | 0.0168 (6) | 0.0307 (8) | 0.0180 (6) | −0.0065 (6) | −0.0018 (5) | −0.0082 (6) |
N1 | 0.0110 (6) | 0.0121 (7) | 0.0110 (6) | −0.0038 (5) | 0.0009 (5) | −0.0034 (5) |
N2 | 0.0139 (7) | 0.0222 (8) | 0.0098 (6) | −0.0043 (6) | −0.0040 (5) | −0.0028 (6) |
C1 | 0.0153 (8) | 0.0106 (8) | 0.0149 (7) | −0.0060 (7) | −0.0018 (6) | −0.0024 (6) |
C2 | 0.0139 (7) | 0.0094 (8) | 0.0138 (7) | −0.0047 (6) | −0.0022 (6) | −0.0022 (6) |
C3 | 0.0123 (7) | 0.0128 (8) | 0.0133 (7) | −0.0025 (6) | 0.0002 (6) | −0.0028 (6) |
C4 | 0.0134 (7) | 0.0157 (9) | 0.0151 (7) | −0.0028 (7) | −0.0028 (6) | −0.0023 (7) |
C5 | 0.0180 (8) | 0.0136 (8) | 0.0118 (7) | −0.0056 (7) | −0.0020 (6) | −0.0017 (6) |
C6 | 0.0167 (8) | 0.0157 (9) | 0.0143 (7) | −0.0035 (7) | 0.0026 (6) | −0.0035 (7) |
C7 | 0.0127 (7) | 0.0126 (8) | 0.0174 (7) | −0.0029 (6) | −0.0017 (6) | −0.0019 (7) |
C8 | 0.0097 (7) | 0.0135 (8) | 0.0126 (7) | −0.0034 (6) | −0.0007 (5) | −0.0019 (6) |
C9 | 0.0127 (7) | 0.0142 (8) | 0.0105 (7) | −0.0038 (6) | 0.0009 (6) | −0.0022 (6) |
C10 | 0.0129 (7) | 0.0085 (8) | 0.0117 (7) | −0.0033 (6) | −0.0019 (6) | −0.0021 (6) |
C11 | 0.0103 (7) | 0.0149 (8) | 0.0146 (7) | −0.0037 (6) | −0.0008 (6) | −0.0021 (6) |
C12 | 0.0113 (7) | 0.0172 (9) | 0.0125 (7) | −0.0033 (7) | 0.0018 (6) | −0.0033 (6) |
C13 | 0.0148 (8) | 0.0105 (8) | 0.0137 (7) | −0.0026 (6) | −0.0030 (6) | −0.0027 (6) |
C14 | 0.0242 (9) | 0.0203 (10) | 0.0133 (7) | −0.0047 (8) | 0.0008 (7) | −0.0033 (7) |
Ni1—O5 | 2.0444 (11) | C2—C7 | 1.391 (2) |
Ni1—O5i | 2.0444 (11) | C3—C2 | 1.401 (2) |
Ni1—O6 | 2.0857 (11) | C3—C4 | 1.377 (2) |
Ni1—O6i | 2.0857 (11) | C3—H3 | 0.9300 |
Ni1—N1 | 2.0978 (12) | C4—H4 | 0.9300 |
Ni1—N1i | 2.0978 (12) | C5—C4 | 1.395 (2) |
O1—C1 | 1.2587 (18) | C5—C6 | 1.393 (2) |
O2—C1 | 1.2616 (18) | C5—C14 | 1.469 (2) |
O3—C14 | 1.216 (2) | C6—C7 | 1.383 (2) |
O4—C13 | 1.2359 (18) | C6—H6 | 0.9300 |
O5—H51 | 0.78 (2) | C7—H7 | 0.9300 |
O5—H52 | 0.90 (2) | C8—H8 | 0.9300 |
O6—H61 | 0.86 (2) | C9—C8 | 1.382 (2) |
O6—H62 | 0.84 (2) | C9—C10 | 1.391 (2) |
O7—H71 | 0.82 (3) | C9—H9 | 0.9300 |
O7—H72 | 0.84 (2) | C10—C11 | 1.388 (2) |
N1—C8 | 1.3465 (18) | C10—C13 | 1.503 (2) |
N1—C12 | 1.3444 (19) | C11—C12 | 1.379 (2) |
N2—C13 | 1.3316 (19) | C11—H11 | 0.9300 |
N2—H21 | 0.84 (2) | C12—H12 | 0.9300 |
N2—H22 | 0.879 (19) | C14—H14 | 0.991 (18) |
C2—C1 | 1.511 (2) | ||
O5i—Ni1—O5 | 180.00 (6) | C4—C3—C2 | 120.18 (14) |
O5—Ni1—O6 | 92.91 (5) | C4—C3—H3 | 119.9 |
O5i—Ni1—O6 | 87.09 (5) | C3—C4—C5 | 120.09 (14) |
O5—Ni1—O6i | 87.09 (5) | C3—C4—H4 | 120.0 |
O5i—Ni1—O6i | 92.91 (5) | C5—C4—H4 | 120.0 |
O5—Ni1—N1 | 91.09 (5) | C4—C5—C6 | 119.94 (14) |
O5i—Ni1—N1 | 88.91 (5) | C4—C5—C14 | 121.06 (14) |
O5—Ni1—N1i | 88.91 (5) | C6—C5—C14 | 119.00 (14) |
O5i—Ni1—N1i | 91.09 (5) | C5—C6—H6 | 120.1 |
O6—Ni1—O6i | 180.00 (8) | C7—C6—C5 | 119.89 (14) |
O6—Ni1—N1 | 90.55 (5) | C7—C6—H6 | 120.1 |
O6i—Ni1—N1 | 89.45 (5) | C2—C7—H7 | 119.8 |
O6—Ni1—N1i | 89.45 (5) | C6—C7—C2 | 120.35 (14) |
O6i—Ni1—N1i | 90.55 (5) | C6—C7—H7 | 119.8 |
N1—Ni1—N1i | 180.00 (3) | N1—C8—C9 | 123.15 (14) |
Ni1—O5—H51 | 116.0 (17) | N1—C8—H8 | 118.4 |
Ni1—O5—H52 | 112.8 (12) | C9—C8—H8 | 118.4 |
H52—O5—H51 | 108 (2) | C8—C9—C10 | 119.38 (13) |
Ni1—O6—H61 | 133.3 (16) | C8—C9—H9 | 120.3 |
Ni1—O6—H62 | 112.7 (15) | C10—C9—H9 | 120.3 |
H61—O6—H62 | 109 (2) | C9—C10—C13 | 124.09 (13) |
H71—O7—H72 | 104 (2) | C11—C10—C9 | 117.58 (13) |
C8—N1—Ni1 | 121.97 (10) | C11—C10—C13 | 118.32 (13) |
C12—N1—Ni1 | 120.69 (9) | C10—C11—H11 | 120.2 |
C12—N1—C8 | 116.97 (13) | C12—C11—C10 | 119.56 (14) |
C13—N2—H21 | 124.0 (12) | C12—C11—H11 | 120.2 |
C13—N2—H22 | 117.6 (12) | N1—C12—C11 | 123.27 (13) |
H21—N2—H22 | 118.0 (17) | N1—C12—H12 | 118.4 |
O1—C1—O2 | 125.32 (14) | C11—C12—H12 | 118.4 |
O1—C1—C2 | 117.63 (14) | O4—C13—N2 | 122.48 (14) |
O2—C1—C2 | 117.04 (13) | O4—C13—C10 | 119.41 (13) |
C3—C2—C1 | 120.57 (13) | N2—C13—C10 | 118.11 (13) |
C7—C2—C1 | 119.88 (14) | O3—C14—C5 | 124.44 (15) |
C7—C2—C3 | 119.54 (14) | O3—C14—H14 | 119.8 (10) |
C2—C3—H3 | 119.9 | C5—C14—H14 | 115.7 (10) |
O5—Ni1—N1—C8 | 120.80 (12) | C4—C3—C2—C7 | −0.6 (2) |
O5i—Ni1—N1—C8 | −59.20 (12) | C2—C3—C4—C5 | 0.0 (2) |
O5—Ni1—N1—C12 | −51.98 (12) | C6—C5—C4—C3 | 1.0 (2) |
O5i—Ni1—N1—C12 | 128.02 (12) | C14—C5—C4—C3 | 179.97 (15) |
O6—Ni1—N1—C8 | −146.28 (12) | C4—C5—C6—C7 | −1.3 (2) |
O6i—Ni1—N1—C8 | 33.72 (12) | C14—C5—C6—C7 | 179.69 (15) |
O6—Ni1—N1—C12 | 40.95 (12) | C4—C5—C14—O3 | 11.3 (3) |
O6i—Ni1—N1—C12 | −139.05 (12) | C6—C5—C14—O3 | −169.77 (17) |
Ni1—N1—C8—C9 | −170.46 (12) | C5—C6—C7—C2 | 0.7 (2) |
C12—N1—C8—C9 | 2.6 (2) | C10—C9—C8—N1 | −0.4 (2) |
Ni1—N1—C12—C11 | 170.82 (12) | C8—C9—C10—C11 | −2.1 (2) |
C8—N1—C12—C11 | −2.3 (2) | C8—C9—C10—C13 | 176.67 (14) |
C3—C2—C1—O1 | −8.1 (2) | C9—C10—C11—C12 | 2.4 (2) |
C3—C2—C1—O2 | 173.07 (14) | C13—C10—C11—C12 | −176.49 (14) |
C7—C2—C1—O1 | 171.16 (14) | C9—C10—C13—O4 | −174.45 (15) |
C7—C2—C1—O2 | −7.7 (2) | C9—C10—C13—N2 | 5.2 (2) |
C1—C2—C7—C6 | −178.93 (14) | C11—C10—C13—O4 | 4.3 (2) |
C3—C2—C7—C6 | 0.3 (2) | C11—C10—C13—N2 | −176.04 (15) |
C4—C3—C2—C1 | 178.61 (14) | C10—C11—C12—N1 | −0.2 (2) |
Symmetry code: (i) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O7ii | 0.84 (2) | 2.03 (2) | 2.8518 (19) | 163.7 (17) |
N2—H22···O3iii | 0.879 (19) | 2.109 (18) | 2.9662 (17) | 165.1 (18) |
O5—H51···O1iv | 0.78 (3) | 1.87 (2) | 2.6485 (16) | 177 (3) |
O5—H52···O2 | 0.897 (19) | 1.847 (19) | 2.7349 (16) | 169.6 (18) |
O6—H61···O1v | 0.87 (3) | 1.91 (3) | 2.7792 (17) | 175 (2) |
O6—H62···O2vi | 0.84 (3) | 1.94 (3) | 2.7710 (17) | 171 (3) |
O7—H71···O3iv | 0.81 (3) | 2.11 (3) | 2.9260 (19) | 176 (2) |
O7—H72···O4 | 0.84 (2) | 1.90 (2) | 2.7333 (18) | 174 (2) |
C9—H9···O7ii | 0.93 | 2.59 | 3.480 (2) | 160 |
C12—H12···O5vii | 0.93 | 2.44 | 3.193 (2) | 138 |
Symmetry codes: (ii) x−1, y, z; (iii) x+1, y−1, z+1; (iv) −x, −y+1, −z; (v) x+1, y−1, z; (vi) x, y−1, z; (vii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C6H6N2O)2(H2O)4](C8H5O3)2·2H2O |
Mr | 709.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 6.4338 (1), 6.9059 (2), 18.1649 (3) |
α, β, γ (°) | 81.658 (2), 85.160 (3), 71.816 (1) |
V (Å3) | 758.01 (3) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.72 |
Crystal size (mm) | 0.35 × 0.15 × 0.1 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.876, 0.928 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14080, 3837, 3259 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.671 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.080, 1.01 |
No. of reflections | 3837 |
No. of parameters | 250 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.50, −0.47 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O7i | 0.84 (2) | 2.03 (2) | 2.8518 (19) | 163.7 (17) |
N2—H22···O3ii | 0.879 (19) | 2.109 (18) | 2.9662 (17) | 165.1 (18) |
O5—H51···O1iii | 0.78 (3) | 1.87 (2) | 2.6485 (16) | 177 (3) |
O5—H52···O2 | 0.897 (19) | 1.847 (19) | 2.7349 (16) | 169.6 (18) |
O6—H61···O1iv | 0.87 (3) | 1.91 (3) | 2.7792 (17) | 175 (2) |
O6—H62···O2v | 0.84 (3) | 1.94 (3) | 2.7710 (17) | 171 (3) |
O7—H71···O3iii | 0.81 (3) | 2.11 (3) | 2.9260 (19) | 176 (2) |
O7—H72···O4 | 0.84 (2) | 1.90 (2) | 2.7333 (18) | 174 (2) |
C9—H9···O7i | 0.93 | 2.59 | 3.480 (2) | 160.00 |
C12—H12···O5vi | 0.93 | 2.44 | 3.193 (2) | 138.00 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y−1, z+1; (iii) −x, −y+1, −z; (iv) x+1, y−1, z; (v) x, y−1, z; (vi) −x+1, −y, −z. |
Acknowledgements
The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2009-FEF-03).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.
The title compound is a monomeric complex, with NiII ion on a centre of symmetry. The structures of some DENA and/or NA complexes of NiII ion, [Ni(C8H5O3)2(C10H14N2O)2(H2O)2] (Sertçelik et al., 2009) and [Ni(C7H4BrO2)2(C6H6N2O)2(H2O)2] (Hökelek et al., 2009) have also been determined.
In the title compound, INA ligands are monodentate. The four O atoms (O5, O6, and the symmetry-related atoms, O5', O6') in the equatorial plane around the Ni atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two pyridine N atoms (N1, N1') of the INA ligands at 2.0978 (12) Å from the Ni atom in the axial positions (Table 1, Fig. 1). The average Ni—O bond length is 2.0651 (11) Å. The O—H···O hydrogen bonds (Table 2) link the coordinated and uncoordinated water molecules to the FB anion and INA ligand, respectively. The dihedral angle between the carboxyl group (O1/O2/C1) and the benzene ring A (C2—C7) is 8.14 (11)°, while that between rings A and B (N1/C8—C12) is 3.46 (6)°.
In the crystal structure, the O—H···O, N—H···O and C—H···O hydrogen bonds (Table 2) link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the structure. The π–π contact between the benzene and pyridine rings, Cg1—Cg2, [where Cg1 and Cg2 are centroids of the rings A (C2—C7) and B (N1/C8—C12), respectively] may further stabilize the structure, with centroid-centroid distance of 3.751 (1) Å.