Literature DB >> 21577450

Tetra-aqua-bis(isonicotinamide-κN)nickel(II) bis-(4-formyl-benzoate) dihydrate.

Tuncer Hökelek, Filiz Yılmaz, Barış Tercan, Ferdi Gürgen, Hacali Necefoğlu.   

Abstract

The asymmetric unit of the title complex, [Ni(C(6)H(6)N(2)O)(2)(H(2)O)(4)](C(8)H(5)O(3))(2)·2H(2)O, contains one-half of the complex cation with the Ni(II) atom located on an inversion center, a 4-formyl-benzoate (FB) counter-anion and an uncoordinated water mol-ecule. The four O atoms in the equatorial plane around the Ni atom form a slightly distorted square-planar arrangement and the slightly distorted octa-hedral 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 carboxyl-ate 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 crystal structure, O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules 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.

Entities:  

Year:  2009        PMID： 21577450      PMCID： PMC2970033          DOI： 10.1107/S1600536809032279

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related 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

[Ni(C6H6N2O)2(H2O)4](C8H5O3)2·2H2O M = 709.28 Triclinic, a = 6.4338 (1) Å b = 6.9059 (2) Å c = 18.1649 (3) Å α = 81.658 (2)° β = 85.160 (3)° γ = 71.816 (1)° V = 758.01 (3) Å3 Z = 1 Mo Kα radiation μ = 0.72 mm−1 T = 100 K 0.35 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.876, T max = 0.928 14080 measured reflections 3837 independent reflections 3259 reflections with I > 2σ(I) R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.080 S = 1.01 3837 reflections 250 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.50 e Å−3 Δρmin = −0.47 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: 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 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032279/xu2589sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032279/xu2589Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ni(C6H6N2O)2(H2O)4](C8H5O3)2·2H2OZ = 1
Mr = 709.28F(000) = 370
Triclinic, P1Dx = 1.554 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.4338 (1) ÅCell parameters from 5282 reflections
b = 6.9059 (2) Åθ = 4.1–28.3°
c = 18.1649 (3) ŵ = 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 diffractometer3837 independent reflections
Radiation source: fine-focus sealed tube3259 reflections with I > 2σ(I)
graphiteRint = 0.067
φ and ω scansθmax = 28.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −8→8
Tmin = 0.876, Tmax = 0.928k = −9→9
14080 measured reflectionsl = −24→24
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0396P)2] where P = (Fo2 + 2Fc2)/3
3837 reflections(Δ/σ)max < 0.001
250 parametersΔρmax = 0.50 e Å−3
0 restraintsΔρmin = −0.47 e Å−3
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.
xyzUiso*/Ueq
Ni10.00000.00000.00000.00952 (9)
O1−0.32770 (17)0.69399 (18)−0.08791 (6)0.0156 (2)
O20.02696 (17)0.55211 (17)−0.11784 (6)0.0147 (2)
O3−0.5543 (2)0.7444 (2)−0.46465 (6)0.0248 (3)
O40.62907 (18)−0.23630 (19)0.31701 (6)0.0187 (3)
O50.18852 (18)0.19178 (18)−0.02699 (6)0.0121 (2)
H510.228 (4)0.229 (4)0.0063 (13)0.050 (8)*
H520.124 (3)0.303 (3)−0.0585 (10)0.027 (5)*
O60.23596 (19)−0.24606 (18)−0.04216 (6)0.0143 (2)
H610.370 (4)−0.265 (4)−0.0591 (12)0.048 (7)*
H620.181 (4)−0.320 (4)−0.0624 (12)0.040 (7)*
O70.8514 (2)−0.1254 (2)0.41718 (7)0.0214 (3)
H710.771 (4)−0.021 (4)0.4322 (13)0.055 (9)*
H720.775 (3)−0.155 (3)0.3879 (12)0.037 (6)*
N10.1326 (2)−0.0939 (2)0.10564 (7)0.0112 (3)
N20.3028 (2)−0.1740 (2)0.37981 (7)0.0153 (3)
H210.166 (3)−0.153 (3)0.3816 (10)0.024 (5)*
H220.369 (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)
H3−0.55800.7218−0.19720.016*
C4−0.4939 (3)0.7027 (3)−0.30658 (8)0.0149 (3)
H4−0.63910.7411−0.31980.018*
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)
H60.00430.5631−0.37710.019*
C7−0.0597 (3)0.5859 (3)−0.26751 (8)0.0144 (3)
H70.08550.5468−0.25430.017*
C80.0066 (2)−0.0685 (2)0.16870 (8)0.0119 (3)
H8−0.1447−0.02680.16510.014*
C90.0914 (2)−0.1014 (2)0.23847 (8)0.0126 (3)
H9−0.0017−0.08120.28060.015*
C100.3172 (2)−0.1649 (2)0.24511 (8)0.0109 (3)
C110.4476 (2)−0.1990 (3)0.18050 (8)0.0133 (3)
H110.5993−0.24650.18280.016*
C120.3506 (2)−0.1620 (3)0.11290 (8)0.0139 (3)
H120.4406−0.18540.07020.017*
C130.4277 (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)*
U11U22U33U12U13U23
Ni10.00852 (14)0.01296 (17)0.00766 (14)−0.00363 (11)−0.00026 (10)−0.00235 (11)
O10.0131 (5)0.0221 (7)0.0133 (5)−0.0060 (5)0.0003 (4)−0.0068 (5)
O20.0121 (5)0.0168 (6)0.0160 (5)−0.0042 (5)−0.0035 (4)−0.0032 (5)
O30.0253 (7)0.0314 (8)0.0150 (6)−0.0030 (6)−0.0067 (5)−0.0039 (5)
O40.0123 (6)0.0267 (7)0.0168 (5)−0.0033 (5)−0.0039 (4)−0.0063 (5)
O50.0122 (5)0.0151 (6)0.0101 (5)−0.0055 (5)−0.0011 (4)−0.0017 (5)
O60.0111 (6)0.0176 (6)0.0159 (5)−0.0048 (5)0.0010 (4)−0.0072 (5)
O70.0168 (6)0.0307 (8)0.0180 (6)−0.0065 (6)−0.0018 (5)−0.0082 (6)
N10.0110 (6)0.0121 (7)0.0110 (6)−0.0038 (5)0.0009 (5)−0.0034 (5)
N20.0139 (7)0.0222 (8)0.0098 (6)−0.0043 (6)−0.0040 (5)−0.0028 (6)
C10.0153 (8)0.0106 (8)0.0149 (7)−0.0060 (7)−0.0018 (6)−0.0024 (6)
C20.0139 (7)0.0094 (8)0.0138 (7)−0.0047 (6)−0.0022 (6)−0.0022 (6)
C30.0123 (7)0.0128 (8)0.0133 (7)−0.0025 (6)0.0002 (6)−0.0028 (6)
C40.0134 (7)0.0157 (9)0.0151 (7)−0.0028 (7)−0.0028 (6)−0.0023 (7)
C50.0180 (8)0.0136 (8)0.0118 (7)−0.0056 (7)−0.0020 (6)−0.0017 (6)
C60.0167 (8)0.0157 (9)0.0143 (7)−0.0035 (7)0.0026 (6)−0.0035 (7)
C70.0127 (7)0.0126 (8)0.0174 (7)−0.0029 (6)−0.0017 (6)−0.0019 (7)
C80.0097 (7)0.0135 (8)0.0126 (7)−0.0034 (6)−0.0007 (5)−0.0019 (6)
C90.0127 (7)0.0142 (8)0.0105 (7)−0.0038 (6)0.0009 (6)−0.0022 (6)
C100.0129 (7)0.0085 (8)0.0117 (7)−0.0033 (6)−0.0019 (6)−0.0021 (6)
C110.0103 (7)0.0149 (8)0.0146 (7)−0.0037 (6)−0.0008 (6)−0.0021 (6)
C120.0113 (7)0.0172 (9)0.0125 (7)−0.0033 (7)0.0018 (6)−0.0033 (6)
C130.0148 (8)0.0105 (8)0.0137 (7)−0.0026 (6)−0.0030 (6)−0.0027 (6)
C140.0242 (9)0.0203 (10)0.0133 (7)−0.0047 (8)0.0008 (7)−0.0033 (7)
Ni1—O52.0444 (11)C2—C71.391 (2)
Ni1—O5i2.0444 (11)C3—C21.401 (2)
Ni1—O62.0857 (11)C3—C41.377 (2)
Ni1—O6i2.0857 (11)C3—H30.9300
Ni1—N12.0978 (12)C4—H40.9300
Ni1—N1i2.0978 (12)C5—C41.395 (2)
O1—C11.2587 (18)C5—C61.393 (2)
O2—C11.2616 (18)C5—C141.469 (2)
O3—C141.216 (2)C6—C71.383 (2)
O4—C131.2359 (18)C6—H60.9300
O5—H510.78 (2)C7—H70.9300
O5—H520.90 (2)C8—H80.9300
O6—H610.86 (2)C9—C81.382 (2)
O6—H620.84 (2)C9—C101.391 (2)
O7—H710.82 (3)C9—H90.9300
O7—H720.84 (2)C10—C111.388 (2)
N1—C81.3465 (18)C10—C131.503 (2)
N1—C121.3444 (19)C11—C121.379 (2)
N2—C131.3316 (19)C11—H110.9300
N2—H210.84 (2)C12—H120.9300
N2—H220.879 (19)C14—H140.991 (18)
C2—C11.511 (2)
O5i—Ni1—O5180.00 (6)C4—C3—C2120.18 (14)
O5—Ni1—O692.91 (5)C4—C3—H3119.9
O5i—Ni1—O687.09 (5)C3—C4—C5120.09 (14)
O5—Ni1—O6i87.09 (5)C3—C4—H4120.0
O5i—Ni1—O6i92.91 (5)C5—C4—H4120.0
O5—Ni1—N191.09 (5)C4—C5—C6119.94 (14)
O5i—Ni1—N188.91 (5)C4—C5—C14121.06 (14)
O5—Ni1—N1i88.91 (5)C6—C5—C14119.00 (14)
O5i—Ni1—N1i91.09 (5)C5—C6—H6120.1
O6—Ni1—O6i180.00 (8)C7—C6—C5119.89 (14)
O6—Ni1—N190.55 (5)C7—C6—H6120.1
O6i—Ni1—N189.45 (5)C2—C7—H7119.8
O6—Ni1—N1i89.45 (5)C6—C7—C2120.35 (14)
O6i—Ni1—N1i90.55 (5)C6—C7—H7119.8
N1—Ni1—N1i180.00 (3)N1—C8—C9123.15 (14)
Ni1—O5—H51116.0 (17)N1—C8—H8118.4
Ni1—O5—H52112.8 (12)C9—C8—H8118.4
H52—O5—H51108 (2)C8—C9—C10119.38 (13)
Ni1—O6—H61133.3 (16)C8—C9—H9120.3
Ni1—O6—H62112.7 (15)C10—C9—H9120.3
H61—O6—H62109 (2)C9—C10—C13124.09 (13)
H71—O7—H72104 (2)C11—C10—C9117.58 (13)
C8—N1—Ni1121.97 (10)C11—C10—C13118.32 (13)
C12—N1—Ni1120.69 (9)C10—C11—H11120.2
C12—N1—C8116.97 (13)C12—C11—C10119.56 (14)
C13—N2—H21124.0 (12)C12—C11—H11120.2
C13—N2—H22117.6 (12)N1—C12—C11123.27 (13)
H21—N2—H22118.0 (17)N1—C12—H12118.4
O1—C1—O2125.32 (14)C11—C12—H12118.4
O1—C1—C2117.63 (14)O4—C13—N2122.48 (14)
O2—C1—C2117.04 (13)O4—C13—C10119.41 (13)
C3—C2—C1120.57 (13)N2—C13—C10118.11 (13)
C7—C2—C1119.88 (14)O3—C14—C5124.44 (15)
C7—C2—C3119.54 (14)O3—C14—H14119.8 (10)
C2—C3—H3119.9C5—C14—H14115.7 (10)
O5—Ni1—N1—C8120.80 (12)C4—C3—C2—C7−0.6 (2)
O5i—Ni1—N1—C8−59.20 (12)C2—C3—C4—C50.0 (2)
O5—Ni1—N1—C12−51.98 (12)C6—C5—C4—C31.0 (2)
O5i—Ni1—N1—C12128.02 (12)C14—C5—C4—C3179.97 (15)
O6—Ni1—N1—C8−146.28 (12)C4—C5—C6—C7−1.3 (2)
O6i—Ni1—N1—C833.72 (12)C14—C5—C6—C7179.69 (15)
O6—Ni1—N1—C1240.95 (12)C4—C5—C14—O311.3 (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—C20.7 (2)
C12—N1—C8—C92.6 (2)C10—C9—C8—N1−0.4 (2)
Ni1—N1—C12—C11170.82 (12)C8—C9—C10—C11−2.1 (2)
C8—N1—C12—C11−2.3 (2)C8—C9—C10—C13176.67 (14)
C3—C2—C1—O1−8.1 (2)C9—C10—C11—C122.4 (2)
C3—C2—C1—O2173.07 (14)C13—C10—C11—C12−176.49 (14)
C7—C2—C1—O1171.16 (14)C9—C10—C13—O4−174.45 (15)
C7—C2—C1—O2−7.7 (2)C9—C10—C13—N25.2 (2)
C1—C2—C7—C6−178.93 (14)C11—C10—C13—O44.3 (2)
C3—C2—C7—C60.3 (2)C11—C10—C13—N2−176.04 (15)
C4—C3—C2—C1178.61 (14)C10—C11—C12—N1−0.2 (2)
D—H···AD—HH···AD···AD—H···A
N2—H21···O7ii0.84 (2)2.03 (2)2.8518 (19)163.7 (17)
N2—H22···O3iii0.879 (19)2.109 (18)2.9662 (17)165.1 (18)
O5—H51···O1iv0.78 (3)1.87 (2)2.6485 (16)177 (3)
O5—H52···O20.897 (19)1.847 (19)2.7349 (16)169.6 (18)
O6—H61···O1v0.87 (3)1.91 (3)2.7792 (17)175 (2)
O6—H62···O2vi0.84 (3)1.94 (3)2.7710 (17)171 (3)
O7—H71···O3iv0.81 (3)2.11 (3)2.9260 (19)176 (2)
O7—H72···O40.84 (2)1.90 (2)2.7333 (18)174 (2)
C9—H9···O7ii0.932.593.480 (2)160
C12—H12···O5vii0.932.443.193 (2)138
Table 1

Selected bond lengths (Å)

Ni1—O52.0444 (11)
Ni1—O62.0857 (11)
Ni1—N12.0978 (12)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H21⋯O7i0.84 (2)2.03 (2)2.8518 (19)163.7 (17)
N2—H22⋯O3ii0.879 (19)2.109 (18)2.9662 (17)165.1 (18)
O5—H51⋯O1iii0.78 (3)1.87 (2)2.6485 (16)177 (3)
O5—H52⋯O20.897 (19)1.847 (19)2.7349 (16)169.6 (18)
O6—H61⋯O1iv0.87 (3)1.91 (3)2.7792 (17)175 (2)
O6—H62⋯O2v0.84 (3)1.94 (3)2.7710 (17)171 (3)
O7—H71⋯O3iii0.81 (3)2.11 (3)2.9260 (19)176 (2)
O7—H72⋯O40.84 (2)1.90 (2)2.7333 (18)174 (2)
C9—H9⋯O7i0.932.593.480 (2)160
C12—H12⋯O5vi0.932.443.193 (2)138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

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4.  Crystal structure and Hirshfeld surface analysis of tetra-aqua-bis-(isonicotinamide-κN 1)nickel(II) fumarate.

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5.  trans-Tetra-aqua-bis-(isonicotinamide-κN (1))zinc bis-(3-hy-droxy-benzoate) tetra-hydrate.

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