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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1708.
Published online 2009 November 28. doi:  10.1107/S1600536809051204
PMCID: PMC2972113

Tetra­aqua­bis[3-(4-pyrid­yl)benzoato-κN]nickel(II)

Abstract

The NiII atom in the title compound, [Ni(C12H8NO2)2(H2O)4], exists in an all-trans octa­hedral coordination environment. The 3-(4-pyrid­yl)benzoate ligand binds to Ni atom through the pyridyl N atom; the pyridine and benzene rings are oriented at a dihedral angle of 26.27 (10)°. Adjacent complexes are linked by O—H(...)O hydrogen bonds, forming a three-dimensional network. The metal atom lies on a special position of 2 site symmetry in the crystal structure.

Related literature

The 3-(pyridin-4-yl)benzoate unit is fairly rigid like the nicotinate unit, which also forms a similar zwitterionic nickel derivative; see: Batten & Harris (2001 [triangle]).

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Object name is e-65-m1708-scheme1.jpg

Experimental

Crystal data

  • [Ni(C12H8NO2)2(H2O)4]
  • M r = 527.16
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1708-efi1.jpg
  • a = 24.564 (3) Å
  • b = 7.0520 (8) Å
  • c = 13.781 (2) Å
  • β = 113.325 (2)°
  • V = 2192.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.94 mm−1
  • T = 173 K
  • 0.47 × 0.31 × 0.08 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.666, T max = 0.929
  • 5587 measured reflections
  • 2360 independent reflections
  • 1977 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.090
  • S = 1.09
  • 2360 reflections
  • 175 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051204/xu2699sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051204/xu2699Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Guangxi Graduate Education Innovation Program (2009106020703M44) and the University of Malaya.

supplementary crystallographic information

Experimental

3-(Pyridin-4-yl)benzoic acid was purchased from a chemical supplier. The reagent (0.199 g, 1 mmol) and sodium hydroxide (0.040 g, 1 mmol) were mixed with nickel(II) nitrate hexahydrate (0.150 g, 0.5 mmol) in water (10 ml). The mixture was placed in a 15 ml Teflon-lined autoclave and heated at 423 K for 48 h. The autoclave was cooled over 12 h at a rate of 5 K an hour. Green crystals were isolated by hand (yield ca 60% based on Ni).

Refinement

Carbon-bound hydrogen atoms were generated geometrically and were constrained to ride on their parent atoms [C–H = 0.95 Å; Uiso(H) =1.2Ueq(C)]. The water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H 0.84±0.01 Å; their temperature factors were refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of Ni(H2O)4(C12H2NO2)2 at the 70% probability level; hydrogen atoms are drawn as sphere of arbitrary radius.

Crystal data

[Ni(C12H8NO2)2(H2O)4]F(000) = 1096
Mr = 527.16Dx = 1.597 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 996 reflections
a = 24.564 (3) Åθ = 3.0–26.9°
b = 7.0520 (8) ŵ = 0.94 mm1
c = 13.781 (2) ÅT = 173 K
β = 113.325 (2)°Prism, green
V = 2192.1 (4) Å30.47 × 0.31 × 0.08 mm
Z = 4

Data collection

Bruker APEXII diffractometer2360 independent reflections
Radiation source: fine-focus sealed tube1977 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→31
Tmin = 0.666, Tmax = 0.929k = −8→8
5587 measured reflectionsl = −17→10

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.09w = 1/[σ2(Fo2) + (0.0539P)2 + 0.5684P] where P = (Fo2 + 2Fc2)/3
2360 reflections(Δ/σ)max = 0.001
175 parametersΔρmax = 0.38 e Å3
4 restraintsΔρmin = −0.27 e Å3

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

xyzUiso*/Ueq
Ni10.50000.30069 (5)0.75000.01561 (13)
N10.58142 (7)0.3092 (2)0.73473 (13)0.0179 (3)
O10.90563 (6)0.2232 (2)0.96391 (12)0.0266 (3)
O20.96160 (6)0.29413 (19)0.87580 (12)0.0242 (3)
O1W0.46891 (6)0.0848 (2)0.64084 (11)0.0199 (3)
O2W0.53247 (6)0.5047 (2)0.86819 (11)0.0208 (3)
C10.91223 (9)0.2740 (3)0.88189 (16)0.0197 (4)
C20.85662 (8)0.3156 (3)0.78537 (16)0.0172 (4)
C30.85969 (8)0.3652 (3)0.69003 (17)0.0208 (4)
H30.89700.37320.68450.025*
C40.80768 (8)0.4029 (3)0.60302 (16)0.0220 (4)
H40.80960.43660.53770.026*
C50.75295 (8)0.3919 (3)0.61016 (15)0.0205 (4)
H50.71780.41880.55000.025*
C60.74932 (8)0.3414 (3)0.70535 (15)0.0176 (4)
C70.80178 (8)0.3043 (3)0.79252 (16)0.0173 (4)
H70.80000.27060.85800.021*
C80.69121 (8)0.3288 (3)0.71474 (16)0.0173 (4)
C90.68658 (8)0.3575 (3)0.81138 (16)0.0198 (4)
H90.72100.38560.87270.024*
C100.63215 (9)0.3452 (3)0.81801 (16)0.0205 (4)
H100.63050.36320.88510.025*
C110.58576 (9)0.2824 (3)0.64134 (16)0.0199 (4)
H11A0.55050.25660.58110.024*
C120.63867 (8)0.2903 (3)0.62852 (16)0.0198 (4)
H12A0.63920.26940.56080.024*
H110.4524 (11)0.124 (4)0.5786 (11)0.048 (9)*
H120.4935 (8)0.004 (3)0.6396 (17)0.023 (6)*
H210.5473 (10)0.452 (3)0.9275 (11)0.030 (7)*
H220.5096 (10)0.591 (3)0.869 (2)0.043 (8)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.01032 (18)0.0186 (2)0.0183 (2)0.0000.00608 (14)0.000
N10.0125 (7)0.0184 (8)0.0222 (9)−0.0001 (6)0.0061 (7)0.0022 (7)
O10.0189 (7)0.0361 (9)0.0215 (8)−0.0012 (6)0.0043 (6)0.0023 (6)
O20.0118 (7)0.0227 (8)0.0362 (9)0.0008 (5)0.0077 (6)0.0012 (6)
O1W0.0155 (7)0.0222 (8)0.0216 (8)0.0010 (6)0.0071 (6)−0.0019 (6)
O2W0.0156 (7)0.0225 (8)0.0226 (8)0.0028 (6)0.0056 (6)−0.0022 (6)
C10.0154 (9)0.0154 (9)0.0259 (11)−0.0002 (7)0.0056 (8)−0.0042 (8)
C20.0149 (9)0.0145 (9)0.0214 (10)−0.0026 (7)0.0064 (8)−0.0045 (8)
C30.0149 (9)0.0215 (10)0.0294 (11)−0.0027 (8)0.0122 (8)−0.0026 (8)
C40.0212 (10)0.0277 (11)0.0202 (10)−0.0032 (8)0.0115 (8)−0.0003 (9)
C50.0158 (9)0.0234 (10)0.0206 (10)−0.0007 (8)0.0054 (8)−0.0002 (8)
C60.0135 (9)0.0176 (9)0.0223 (10)−0.0020 (7)0.0078 (8)−0.0033 (7)
C70.0156 (9)0.0179 (9)0.0187 (9)0.0002 (7)0.0071 (8)0.0002 (8)
C80.0149 (9)0.0163 (9)0.0205 (10)0.0014 (7)0.0069 (8)0.0024 (7)
C90.0130 (9)0.0242 (10)0.0204 (10)0.0011 (8)0.0047 (8)0.0004 (8)
C100.0175 (9)0.0255 (10)0.0198 (10)0.0014 (8)0.0090 (8)0.0003 (8)
C110.0139 (9)0.0237 (10)0.0210 (10)−0.0004 (8)0.0057 (8)0.0008 (8)
C120.0167 (10)0.0230 (10)0.0196 (10)−0.0007 (8)0.0071 (8)−0.0007 (8)

Geometric parameters (Å, °)

Ni1—O1W2.0627 (14)C3—C41.388 (3)
Ni1—O1Wi2.0627 (14)C3—H30.9500
Ni1—O2W2.0811 (14)C4—C51.389 (3)
Ni1—O2Wi2.0811 (14)C4—H40.9500
Ni1—N1i2.0931 (16)C5—C61.396 (3)
Ni1—N12.0931 (16)C5—H50.9500
N1—C101.342 (3)C6—C71.395 (3)
N1—C111.346 (2)C6—C81.486 (3)
O1—C11.256 (3)C7—H70.9500
O2—C11.256 (2)C8—C121.392 (3)
O1W—H110.838 (10)C8—C91.396 (3)
O1W—H120.834 (10)C9—C101.378 (3)
O2W—H210.840 (10)C9—H90.9500
O2W—H220.833 (10)C10—H100.9500
C1—C21.511 (3)C11—C121.380 (3)
C2—C31.390 (3)C11—H11A0.9500
C2—C71.391 (3)C12—H12A0.9500
O1W—Ni1—O1Wi84.85 (8)C4—C3—C2119.26 (17)
O1W—Ni1—O2W176.09 (6)C4—C3—H3120.4
O1Wi—Ni1—O2W91.32 (6)C2—C3—H3120.4
O1W—Ni1—O2Wi91.32 (6)C3—C4—C5120.92 (18)
O1Wi—Ni1—O2Wi176.09 (6)C3—C4—H4119.5
O2W—Ni1—O2Wi92.51 (8)C5—C4—H4119.5
O1W—Ni1—N1i90.11 (6)C4—C5—C6120.31 (18)
O1Wi—Ni1—N1i92.32 (6)C4—C5—H5119.8
O2W—Ni1—N1i89.24 (6)C6—C5—H5119.8
O2Wi—Ni1—N1i88.48 (6)C7—C6—C5118.45 (17)
O1W—Ni1—N192.32 (6)C7—C6—C8120.35 (17)
O1Wi—Ni1—N190.11 (6)C5—C6—C8121.19 (17)
O2W—Ni1—N188.48 (6)C2—C7—C6121.21 (18)
O2Wi—Ni1—N189.24 (6)C2—C7—H7119.4
N1i—Ni1—N1176.71 (9)C6—C7—H7119.4
C10—N1—C11116.48 (16)C12—C8—C9116.40 (17)
C10—N1—Ni1121.33 (13)C12—C8—C6122.37 (18)
C11—N1—Ni1122.18 (13)C9—C8—C6121.23 (17)
Ni1—O1W—H11113 (2)C10—C9—C8120.12 (18)
Ni1—O1W—H12117.0 (16)C10—C9—H9119.9
H11—O1W—H12105 (2)C8—C9—H9119.9
Ni1—O2W—H21109.7 (18)N1—C10—C9123.49 (18)
Ni1—O2W—H22117.8 (19)N1—C10—H10118.3
H21—O2W—H22110 (2)C9—C10—H10118.3
O1—C1—O2124.36 (19)N1—C11—C12123.49 (19)
O1—C1—C2116.99 (17)N1—C11—H11A118.3
O2—C1—C2118.65 (18)C12—C11—H11A118.3
C3—C2—C7119.85 (18)C11—C12—C8120.03 (19)
C3—C2—C1120.82 (17)C11—C12—H12A120.0
C7—C2—C1119.32 (18)C8—C12—H12A120.0
O1W—Ni1—N1—C10−144.22 (15)C3—C2—C7—C60.1 (3)
O1Wi—Ni1—N1—C10−59.36 (15)C1—C2—C7—C6−179.93 (17)
O2W—Ni1—N1—C1031.96 (15)C5—C6—C7—C2−0.4 (3)
O2Wi—Ni1—N1—C10124.49 (15)C8—C6—C7—C2−179.88 (17)
O1W—Ni1—N1—C1136.93 (15)C7—C6—C8—C12−154.18 (19)
O1Wi—Ni1—N1—C11121.79 (15)C5—C6—C8—C1226.4 (3)
O2W—Ni1—N1—C11−146.89 (15)C7—C6—C8—C926.6 (3)
O2Wi—Ni1—N1—C11−54.36 (15)C5—C6—C8—C9−152.89 (19)
O1—C1—C2—C3−177.38 (18)C12—C8—C9—C100.6 (3)
O2—C1—C2—C33.5 (3)C6—C8—C9—C10179.95 (18)
O1—C1—C2—C72.7 (3)C11—N1—C10—C90.8 (3)
O2—C1—C2—C7−176.42 (17)Ni1—N1—C10—C9−178.14 (15)
C7—C2—C3—C40.0 (3)C8—C9—C10—N1−1.1 (3)
C1—C2—C3—C4−179.89 (18)C10—N1—C11—C120.0 (3)
C2—C3—C4—C50.1 (3)Ni1—N1—C11—C12178.89 (14)
C3—C4—C5—C6−0.4 (3)N1—C11—C12—C8−0.4 (3)
C4—C5—C6—C70.5 (3)C9—C8—C12—C110.1 (3)
C4—C5—C6—C8179.99 (18)C6—C8—C12—C11−179.22 (18)

Symmetry codes: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1w—H11···O1ii0.84 (1)1.88 (1)2.682 (2)160 (3)
O1w—H12···O2iii0.83 (1)1.91 (1)2.734 (2)170 (2)
O2w—H21···O1iv0.84 (1)1.93 (1)2.732 (2)159 (2)
O2w—H22···O2v0.83 (1)1.88 (1)2.711 (2)177 (3)

Symmetry codes: (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+3/2, −y+1/2, −z+2; (v) x−1/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2699).

References

  • Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  • Batten, S. R. & Harris, A. R. (2001). Acta Cryst. E57, m9–m11.
  • Bruker (2004). APEX2 and SAINT. Bruker AXS inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.

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