PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): m585.
Published online 2008 March 29. doi:  10.1107/S1600536808007836
PMCID: PMC2960908

Hexaaqua­nickel(II) bis­{4-[(2-chlorothia­zol-5-yl)meth­oxy]benzoate} dihydrate

Abstract

In the title compound, [Ni(H2O)6](C11H7ClNO3S)2·2H2O, the NiII atom lies on an inversion center and is six-coordinate in an octa­hedral environment of water mol­ecules. The cation and anion are linked through O—H(...)O hydrogen bonding involving the coordinated and uncoordinated water mol­ecules into a three-dimensional network.

Related literature

For the synthesis of 4-[(2-chloro-5-thia­zolyl)meth­oxy]benzoic acid, see: Mirci (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m585-scheme1.jpg

Experimental

Crystal data

  • [Ni(H2O)6](C11H7ClNO3S)2·2H2O
  • M r = 740.21
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m585-efi1.jpg
  • a = 7.1844 (4) Å
  • b = 7.2084 (4) Å
  • c = 15.5621 (8) Å
  • α = 78.388 (1)°
  • β = 81.285 (1)°
  • γ = 71.734 (1)°
  • V = 746.26 (7) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.04 mm−1
  • T = 291 (2) K
  • 0.20 × 0.18 × 0.08 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.819, T max = 0.921
  • 4613 measured reflections
  • 2862 independent reflections
  • 2496 reflections with I > 2σ(I)
  • R int = 0.012

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.075
  • S = 1.06
  • 2862 reflections
  • 196 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808007836/ng2435sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007836/ng2435Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support from the China West Normal University and Heilongjiang University.

supplementary crystallographic information

Comment

Simple carboxylic acids exhibit a variety of superamolecular aggregation patterns. Recenttly,our attention has been focused on 4-[(2-Chloro-5-thiazolyl)methoxy]Benzoic acid, it is a intermediate used in the synthesis of pesticide. In this paper, we reprot a new complex, (I), synthesized by the reaction of 4-[(2-chloro-5-thiazolyl)methoxy]benzoic acid and nickel(II) nitrate hexahydrate in an aqueous solution.

The asymmetric unit of (I) consists of a hexaaquanickel(II) cation, two 4-[(2-chloro-5-thiazolyl)methoxy]benzoate anions and noe uncoordinated water molecules(Fig. 1). The Ni(II) atom lies on an inversion and is coordinated by six water molecules in an octahedral environment. The anion is almost planar,the largest deviation being 0.136 (5) Å for atom Cl1.

All cations, anions and uncoordinated water molecules are linked through O—H···O hydrogen bonds,resulting in a three-dimensional supramolecular network(Fig. 2; Table 1).

Experimental

4-[(2-Chloro-5-thiazolyl)methoxy]benzoic acid was prepared by substitute reaction of 4-hydroxybenzoic acid and 2-chloro-5-chloromethoxythiazol under basic conditions(stephen et al.,2000). Nickel nitrate hexahydrate(0.582 g, 2 mmol) and 4-[(2-Chloro-5-thiazolyl)methoxy]benzoic acid(0.538 g, 2 mmol) were dissolved in water(15 ml) and the pH was adjusted to 7 with 0.01 mol/L sodium hydroxide. Jade-green crystals separated from filtered after several days.

Refinement

H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic C), C—H = 0.97 Å (methylene C), and with Uiso(H) = 1.2Ueq(C). Water H atoms were initially located in a difference Fourier map but they were treated as riding on their parent atoms with O—H=0.85 Å, Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of (I) with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. A dashed line indicates the intermolecular O—H···O ...
Fig. 2.
A partial packing view, showing the three-dimensional network. Dashed lines indicate the hydrogen-bonding interactions. The H atoms have been omitted for clarity.

Crystal data

[Ni(H2O)6](C11H7ClNO3S)2·2H2OZ = 1
Mr = 740.21F000 = 382
Triclinic, P1Dx = 1.647 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.1844 (4) ÅCell parameters from 4613 reflections
b = 7.2084 (4) Åθ = 2.7–28.2º
c = 15.5621 (8) ŵ = 1.04 mm1
α = 78.388 (1)ºT = 291 (2) K
β = 81.285 (1)ºBlock, green
γ = 71.734 (1)º0.20 × 0.18 × 0.08 mm
V = 746.26 (7) Å3

Data collection

Rigaku R-AXIS RAPID diffractometer2862 independent reflections
Radiation source: fine-focus sealed tube2496 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.012
T = 291(2) Kθmax = 26.0º
ω scanθmin = 2.7º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)h = −8→8
Tmin = 0.819, Tmax = 0.922k = −4→8
4613 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.076  w = 1/[σ2(Fo2) + (0.0324P)2 + 0.4113P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2862 reflectionsΔρmax = 0.36 e Å3
196 parametersΔρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
C10.4407 (3)0.4075 (3)0.34973 (14)0.0299 (5)
C20.5199 (3)0.3065 (3)0.27064 (14)0.0290 (4)
C30.5491 (3)0.4165 (3)0.18875 (14)0.0341 (5)
H10.52310.55280.18360.041*
C40.6166 (3)0.3275 (3)0.11385 (15)0.0377 (5)
H20.63670.40310.05930.045*
C50.6532 (3)0.1257 (3)0.12194 (14)0.0357 (5)
C60.6261 (4)0.0128 (3)0.20322 (15)0.0454 (6)
H30.6515−0.12340.20810.055*
C70.5612 (4)0.1027 (3)0.27714 (15)0.0414 (6)
H40.54500.02600.33180.050*
C80.7285 (4)0.1271 (3)−0.03345 (14)0.0404 (5)
H60.81820.2060−0.03880.048*
H50.59990.2151−0.04740.048*
C90.8018 (3)−0.0208 (3)−0.09460 (14)0.0336 (5)
C100.8419 (4)0.0072 (4)−0.18299 (15)0.0444 (6)
H70.82520.1330−0.21620.053*
C110.9178 (3)−0.3136 (3)−0.16161 (15)0.0369 (5)
Cl10.99611 (11)−0.54983 (9)−0.18443 (5)0.05607 (19)
N10.9093 (3)−0.1615 (3)−0.22133 (13)0.0431 (5)
Ni11.00000.00000.50000.02618 (11)
O10.4168 (2)0.2996 (2)0.42325 (10)0.0360 (4)
O20.4022 (2)0.5919 (2)0.33923 (10)0.0420 (4)
O30.7165 (3)0.0213 (2)0.05258 (10)0.0521 (5)
O41.0411 (2)−0.1930 (2)0.41173 (11)0.0435 (4)
H80.9563−0.25150.40970.065*
H91.1530−0.26630.39460.065*
O50.9559 (3)0.2269 (2)0.39824 (11)0.0519 (5)
H101.00580.20930.34630.078*
H110.89940.34830.40140.078*
O60.7076 (2)0.0327 (2)0.52300 (11)0.0403 (4)
H120.62860.11760.48880.061*
H130.6671−0.06860.54110.061*
O70.2566 (2)0.3897 (2)0.58489 (11)0.0418 (4)
H150.35370.37650.61310.063*
H140.30160.37780.53190.063*
S10.84843 (10)−0.26984 (9)−0.05532 (4)0.04168 (16)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0288 (10)0.0311 (12)0.0304 (11)−0.0066 (9)−0.0005 (8)−0.0112 (9)
C20.0305 (10)0.0267 (11)0.0279 (11)−0.0039 (8)−0.0003 (8)−0.0090 (9)
C30.0447 (12)0.0248 (11)0.0319 (12)−0.0084 (9)0.0001 (9)−0.0082 (9)
C40.0515 (13)0.0326 (12)0.0258 (11)−0.0108 (10)0.0030 (10)−0.0049 (9)
C50.0450 (12)0.0313 (12)0.0270 (11)−0.0040 (10)0.0032 (9)−0.0126 (9)
C60.0708 (17)0.0232 (12)0.0336 (13)−0.0049 (11)0.0067 (12)−0.0080 (10)
C70.0600 (15)0.0301 (12)0.0268 (11)−0.0074 (11)0.0080 (10)−0.0065 (10)
C80.0577 (14)0.0332 (13)0.0272 (12)−0.0087 (11)0.0025 (10)−0.0104 (10)
C90.0417 (12)0.0282 (11)0.0291 (11)−0.0076 (9)0.0003 (9)−0.0075 (9)
C100.0702 (16)0.0297 (12)0.0284 (12)−0.0098 (11)0.0028 (11)−0.0071 (10)
C110.0434 (12)0.0328 (12)0.0327 (12)−0.0067 (10)0.0022 (10)−0.0126 (10)
Cl10.0756 (5)0.0341 (3)0.0554 (4)−0.0099 (3)0.0077 (3)−0.0205 (3)
N10.0622 (13)0.0352 (11)0.0283 (10)−0.0085 (9)0.0044 (9)−0.0130 (9)
Ni10.0301 (2)0.0224 (2)0.0240 (2)−0.00492 (15)0.00206 (14)−0.00691 (15)
O10.0464 (9)0.0331 (8)0.0274 (8)−0.0104 (7)0.0037 (7)−0.0098 (7)
O20.0575 (10)0.0278 (8)0.0362 (9)−0.0050 (7)0.0040 (7)−0.0130 (7)
O30.0902 (14)0.0318 (9)0.0255 (8)−0.0070 (9)0.0071 (8)−0.0114 (7)
O40.0432 (9)0.0421 (10)0.0493 (10)−0.0121 (7)0.0064 (7)−0.0255 (8)
O50.0836 (13)0.0268 (9)0.0277 (8)0.0023 (8)0.0087 (8)−0.0048 (7)
O60.0340 (8)0.0358 (9)0.0482 (10)−0.0101 (7)0.0004 (7)−0.0035 (7)
O70.0494 (9)0.0378 (9)0.0371 (9)−0.0085 (7)0.0032 (7)−0.0159 (7)
S10.0599 (4)0.0318 (3)0.0279 (3)−0.0089 (3)0.0050 (3)−0.0064 (2)

Geometric parameters (Å, °)

C1—O21.251 (3)C10—N11.380 (3)
C1—O11.269 (3)C10—H70.9300
C1—C21.503 (3)C11—N11.279 (3)
C2—C31.383 (3)C11—Cl11.710 (2)
C2—C71.390 (3)C11—S11.716 (2)
C3—C41.393 (3)Ni1—O52.0167 (16)
C3—H10.9300Ni1—O5i2.0167 (16)
C4—C51.378 (3)Ni1—O6i2.0230 (15)
C4—H20.9300Ni1—O62.0230 (15)
C5—O31.379 (3)Ni1—O4i2.0732 (15)
C5—C61.382 (3)Ni1—O42.0732 (15)
C6—C71.381 (3)O4—H80.8499
C6—H30.9300O4—H90.8500
C7—H40.9300O5—H100.8500
C8—O31.406 (3)O5—H110.8500
C8—C91.492 (3)O6—H120.8499
C8—H60.9700O6—H130.8500
C8—H50.9700O7—H150.8499
C9—C101.349 (3)O7—H140.8501
C9—S11.718 (2)
O2—C1—O1124.10 (19)N1—C10—H7121.9
O2—C1—C2118.33 (19)N1—C11—Cl1122.70 (17)
O1—C1—C2117.58 (19)N1—C11—S1116.45 (17)
C3—C2—C7118.43 (19)Cl1—C11—S1120.85 (14)
C3—C2—C1120.19 (19)C11—N1—C10109.39 (19)
C7—C2—C1121.36 (19)O5—Ni1—O5i180.000 (1)
C2—C3—C4121.4 (2)O5—Ni1—O6i88.79 (7)
C2—C3—H1119.3O5i—Ni1—O6i91.21 (7)
C4—C3—H1119.3O5—Ni1—O691.21 (7)
C5—C4—C3118.9 (2)O5i—Ni1—O688.79 (7)
C5—C4—H2120.5O6i—Ni1—O6180.00 (9)
C3—C4—H2120.5O5—Ni1—O4i91.14 (7)
C4—C5—O3124.3 (2)O5i—Ni1—O4i88.86 (7)
C4—C5—C6120.6 (2)O6i—Ni1—O4i92.92 (6)
O3—C5—C6115.1 (2)O6—Ni1—O4i87.08 (6)
C7—C6—C5119.9 (2)O5—Ni1—O488.86 (7)
C7—C6—H3120.0O5i—Ni1—O491.14 (7)
C5—C6—H3120.0O6i—Ni1—O487.08 (6)
C6—C7—C2120.7 (2)O6—Ni1—O492.92 (6)
C6—C7—H4119.6O4i—Ni1—O4180.0
C2—C7—H4119.6C5—O3—C8118.64 (18)
O3—C8—C9107.34 (18)Ni1—O4—H8121.8
O3—C8—H6110.2Ni1—O4—H9123.8
C9—C8—H6110.2H8—O4—H9107.5
O3—C8—H5110.2Ni1—O5—H10121.0
C9—C8—H5110.2Ni1—O5—H11126.5
H6—C8—H5108.5H10—O5—H11112.2
C10—C9—C8129.8 (2)Ni1—O6—H12120.0
C10—C9—S1109.38 (17)Ni1—O6—H13119.8
C8—C9—S1120.84 (16)H12—O6—H13109.8
C9—C10—N1116.1 (2)H15—O7—H14107.2
C9—C10—H7121.9C11—S1—C988.63 (11)

Symmetry codes: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H8···O7ii0.852.052.903 (2)175
O4—H9···O2iii0.851.932.776 (2)172
O5—H10···N1iv0.852.012.858 (2)173
O5—H11···O7v0.851.912.750 (2)173
O6—H12···O10.851.942.781 (2)171
O6—H13···O1ii0.851.902.747 (2)177
O7—H14···O10.851.882.718 (2)169

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2435).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Mirci, L. E. (1990). Rom. Patent No. 0 743 205.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography