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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page m1482
https://doi.org/10.1107/S160053680904464X

Poly[[[bis­­(acetato-κO)copper(II)]-μ-1,4-diimidazol-1-ylbenzene-κ2N3:N3′] dihydrate]

Yi-Fang Deng,a Man-Sheng Chen,a* Dai-Zhi Kuanga* and Chun-Hua Zhanga

aKey Laboratory of Functional Organometallic Materials, Hengyang Normal University, Department of Chemistry and Materials Science, Hengyang, Hunan 421008, People's Republic of China
*Correspondence e-mail: cmsniu@163.com, hnkdz@yahoo.com.cn

(Received 22 October 2009; accepted 27 October 2009; online 31 October 2009)

In the title linear coordination polymer, {[Cu(C2H3O2)2(C12H10N4)]·2H2O}n, the CuII atom is coordinated by two N atoms from two different symmetry-related 1,4-diimidazol-1-ylbenzene (dib) ligands and two carboxyl­ate O atoms from two acetate ligands in a square-planar geometry. The Cu atoms are linked by the dib ligands, forming an extended chain. These chains are linked by O—H⋯O hydrogen bonds into a three-dimensional supra­molecular network. The CuII atom lies on a center of inversion.

Related literature

For the potential applications of crystalline materials with framework structures, see: Kitagawa & Kondo (1998[Kitagawa, S. & Kondo, M. (1998). Bull. Chem. Soc. Jpn, 71, 1739-1753.]). For copper complexes with the imidazole heterocycle, see: Huang et al. (2004[Huang, X. C., Zhang, J. P., Lin, Y. Y., Yu, X. L. & Chen, X. M. (2004). Chem. Commun. pp. 1100-1101.]); Masciocchi et al. (2001[Masciocchi, N., Bruni, S., Cariati, E., Cariati, F., Galli, S. & Sironi, A. (2001). Inorg. Chem. 40, 5897-5905.]). For C—O bond lengths, see: Dong et al. (2009[Dong, H., Bi, W. & Zhu, H. (2009). Asian J. Chem. 21, 5598-5602.]). For a related structure, see: Xie et al. (2007[Xie, J., Chen, X., Liu, G. X. & Sun, W. Y. (2007). Chin. J. Inorg. Chem. 23, 1295-1298.]).

[Scheme 1]

Experimental

Crystal data

  • [Cu(C2H3O2)2(C12H10N4)]·2H2O

  • Mr = 427.90

  • Triclinic, [P \overline 1]

  • a = 4.707 (2) Å

  • b = 9.444 (3) Å

  • c = 10.901 (5) Å

  • α = 72.569 (5)°

  • β = 82.956 (4)°

  • γ = 76.766 (5)°

  • V = 449.3 (3) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.26 mm−1

  • T = 293 K

  • 0.24 × 0.18 × 0.12 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.752, Tmax = 0.864

  • 2248 measured reflections

  • 1562 independent reflections

  • 1530 reflections with I > 2σ(I)

  • Rint = 0.041
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.06

  • 1562 reflections

  • 125 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1W—H1WA⋯O2 0.85 1.94 2.792 (6) 176
O1W—H1WB⋯O1Wi 0.90 2.31 2.807 (7) 114
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: APEX2 (Bruker, 2003[Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL .

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680904464X/ng2675sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904464X/ng2675Isup2.hkl

checkCIF report


Comment top

Recently, a great deal of interest in transition metal complex assembly has been devoted to the development of rational synthetic routes to novel one-, two- and three-dimensional crystal frameworks, due to their potential applications in many areas (Kitagawa, et al., 1998). Particularly, copper complexes with the imidazole heterocycle have been investigated extensively to date (Huang, et al., 2004; Masciocchi et al., 2001). Furthermore, many crystal structures of copper(II) compounds with 4,4'-bipyridine have been determined so far. However, ligand 1,4-diimidazol-1-ylbenzene (dib) is similar to the 4,4'-bipyridine, only one structure of copper complex is known (Xie, et al., 2007). So we have recently prepared a new copper(II) coordination polymer, [Cu(dib)(CH3COO)2]n.2nH2O, (I), with 1,4-diimidazol-1-ylbenzene and copper acetate.

In the title compound, the central CuII ion is four-coordinated by two N atoms from two different dib ligands, two carboxylate O atoms from two acetate ligands in a square planar coordination geometry(Fig. 1). There is one free water molecule in the structure, stabilized by hydrogen bonds. The Cu—O distances are comparable to those found in other crystallographically characterized CuII complexes (Dong et al., 2009). The Cu atoms are linked by the dib ligands, forming an extended chain. These chains are further connected by O—H···O bonds (Table 2) to form a three-dimensional supramolecular architecture (Fig. 2).

Related literature top

For the potential applications of crystal frameworks, see: Kitagawa & Kondo (1998). For copper complexes with the imidazole heterocycle, see: Huang et al. (2004); Masciocchi et al. (2001). For C—O bond lengths, see: Dong et al. (2009). For a related structure, see: Xie et al. (2007).

Experimental top

A mixture of Cu(CH3CO2)2.2H2O (0.040 g, 0.2 mmol), 1,4-diimidazol-1-ylbenzene (0.042 g, 0.2 mmol), and H2O (15 ml) was sealed in a 25 ml Teflon-lined stainless steel reactor, which was heated at 433 K for 72 h and then it was cooled to room temperature. Block blue crystals of the title compound were collected.

Refinement top

H atoms bonded to C atoms were placed geometrically and treated as riding. The water H atoms found from Fourier difference maps were refined with restraints for O—H distances (0.8499–0.9046 Å) with Uiso(H) = 1.2Ueq(O).

Structure description top

Recently, a great deal of interest in transition metal complex assembly has been devoted to the development of rational synthetic routes to novel one-, two- and three-dimensional crystal frameworks, due to their potential applications in many areas (Kitagawa, et al., 1998). Particularly, copper complexes with the imidazole heterocycle have been investigated extensively to date (Huang, et al., 2004; Masciocchi et al., 2001). Furthermore, many crystal structures of copper(II) compounds with 4,4'-bipyridine have been determined so far. However, ligand 1,4-diimidazol-1-ylbenzene (dib) is similar to the 4,4'-bipyridine, only one structure of copper complex is known (Xie, et al., 2007). So we have recently prepared a new copper(II) coordination polymer, [Cu(dib)(CH3COO)2]n.2nH2O, (I), with 1,4-diimidazol-1-ylbenzene and copper acetate.

In the title compound, the central CuII ion is four-coordinated by two N atoms from two different dib ligands, two carboxylate O atoms from two acetate ligands in a square planar coordination geometry(Fig. 1). There is one free water molecule in the structure, stabilized by hydrogen bonds. The Cu—O distances are comparable to those found in other crystallographically characterized CuII complexes (Dong et al., 2009). The Cu atoms are linked by the dib ligands, forming an extended chain. These chains are further connected by O—H···O bonds (Table 2) to form a three-dimensional supramolecular architecture (Fig. 2).

For the potential applications of crystal frameworks, see: Kitagawa & Kondo (1998). For copper complexes with the imidazole heterocycle, see: Huang et al. (2004); Masciocchi et al. (2001). For C—O bond lengths, see: Dong et al. (2009). For a related structure, see: Xie et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level.
[Figure 2] Fig. 2. Projection showing the three-dimensional structure formed by H-bonding interaction of the compound (I).
Poly[[[bis(acetato-κO)copper(II)]-µ-1,4-diimidazol-1-ylbenzene- κ2N3:N3'] dihydrate] top
Crystal data top
[Cu(C2H3O2)2(C12H10N4)]·2H2OZ = 1
Mr = 427.90F(000) = 221
Triclinic, P1Dx = 1.581 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 4.707 (2) ÅCell parameters from 2023 reflections
b = 9.444 (3) Åθ = 2.3–28.2°
c = 10.901 (5) ŵ = 1.26 mm−1
α = 72.569 (5)°T = 293 K
β = 82.956 (4)°Block, blue
γ = 76.766 (5)°0.24 × 0.18 × 0.12 mm
V = 449.3 (3) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		1562 independent reflections
Radiation source: fine-focus sealed tube1530 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −5→5
Tmin = 0.752, Tmax = 0.864k = −11→11
2248 measured reflectionsl = −10→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.4024P]
where P = (Fo2 + 2Fc2)/3
1562 reflections(Δ/σ)max = 0.001
125 parametersΔρmax = 0.45 e Å−3
2 restraintsΔρmin = −0.40 e Å−3
Crystal data top
[Cu(C2H3O2)2(C12H10N4)]·2H2Oγ = 76.766 (5)°
Mr = 427.90V = 449.3 (3) Å3
Triclinic, P1Z = 1
a = 4.707 (2) ÅMo Kα radiation
b = 9.444 (3) ŵ = 1.26 mm−1
c = 10.901 (5) ÅT = 293 K
α = 72.569 (5)°0.24 × 0.18 × 0.12 mm
β = 82.956 (4)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		1562 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1530 reflections with I > 2σ(I)
Tmin = 0.752, Tmax = 0.864Rint = 0.041
2248 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0362 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.06Δρmax = 0.45 e Å−3
1562 reflectionsΔρmin = −0.40 e Å−3
125 parameters
Special details top

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) top
xyzUiso*/Ueq
O20.6552 (9)0.2222 (4)0.7045 (4)0.0507 (10)
O1W0.7740 (10)−0.0100 (5)0.9321 (4)0.0573 (11)
H1WB0.77090.02850.99900.069*
H1WA0.73370.06380.86520.069*
Cu10.50000.50000.50000.0298 (3)
C10.3713 (15)0.0609 (6)0.6676 (7)0.0583 (16)
H1A0.5335−0.01540.65190.087*
H1B0.21850.07310.61220.087*
H1C0.29950.03070.75590.087*
C20.4695 (11)0.2091 (5)0.6405 (5)0.0376 (11)
C30.2141 (12)0.7070 (5)0.6631 (5)0.0386 (11)
H30.32490.77970.62210.046*
C40.0188 (11)0.7151 (5)0.7622 (5)0.0391 (11)
H4−0.03010.79280.80170.047*
C50.0373 (10)0.5061 (5)0.7114 (4)0.0331 (10)
H5−0.00060.41360.71160.040*
C6−0.4029 (12)0.6328 (6)0.9800 (5)0.0404 (12)
H6−0.33790.72250.96660.049*
C7−0.3994 (11)0.4103 (6)0.9189 (5)0.0398 (12)
H7−0.33170.34950.86400.048*
C8−0.3014 (10)0.5423 (5)0.8984 (4)0.0293 (9)
N10.2268 (9)0.5756 (4)0.6310 (4)0.0322 (9)
N2−0.0957 (8)0.5866 (4)0.7941 (4)0.0299 (8)
O10.3507 (8)0.3154 (4)0.5476 (3)0.0382 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.063 (3)0.041 (2)0.051 (2)−0.0131 (18)−0.007 (2)−0.0136 (18)
O1W0.071 (3)0.050 (2)0.049 (2)−0.014 (2)−0.007 (2)−0.0092 (18)
Cu10.0370 (5)0.0274 (5)0.0243 (5)−0.0070 (3)0.0054 (3)−0.0088 (3)
C10.072 (4)0.035 (3)0.068 (4)−0.021 (3)−0.001 (3)−0.010 (3)
C20.046 (3)0.031 (2)0.037 (3)−0.011 (2)0.014 (2)−0.016 (2)
C30.049 (3)0.032 (2)0.038 (3)−0.014 (2)0.012 (2)−0.015 (2)
C40.048 (3)0.032 (2)0.040 (3)−0.011 (2)0.012 (2)−0.018 (2)
C50.039 (3)0.031 (2)0.030 (2)−0.0069 (19)0.006 (2)−0.0133 (19)
C60.052 (3)0.034 (2)0.041 (3)−0.016 (2)0.014 (2)−0.019 (2)
C70.049 (3)0.038 (3)0.038 (3)−0.010 (2)0.014 (2)−0.024 (2)
C80.030 (2)0.033 (2)0.025 (2)−0.0040 (18)0.0030 (17)−0.0110 (18)
N10.039 (2)0.0294 (19)0.0279 (19)−0.0059 (16)0.0075 (16)−0.0112 (16)
N20.0329 (19)0.0298 (19)0.0269 (19)−0.0045 (15)0.0052 (15)−0.0119 (15)
O10.048 (2)0.0325 (17)0.0345 (18)−0.0127 (15)0.0089 (15)−0.0112 (15)
Geometric parameters (Å, º) top
O2—C21.231 (6)C3—H30.9300
O1W—H1WB0.9046C4—N21.373 (6)
O1W—H1WA0.8499C4—H40.9300
Cu1—O11.932 (3)C5—N11.314 (6)
Cu1—O1i1.932 (3)C5—N21.355 (6)
Cu1—N11.986 (4)C5—H50.9300
Cu1—N1i1.986 (4)C6—C7ii1.379 (7)
C1—C21.509 (7)C6—C81.384 (6)
C1—H1A0.9600C6—H60.9300
C1—H1B0.9600C7—C81.374 (7)
C1—H1C0.9600C7—C6ii1.379 (7)
C2—O11.273 (6)C7—H70.9300
C3—C41.338 (7)C8—N21.427 (6)
C3—N11.374 (6)
H1WB—O1W—H1WA107.9N2—C4—H4126.6
O1—Cu1—O1i180.000 (1)N1—C5—N2111.3 (4)
O1—Cu1—N190.62 (15)N1—C5—H5124.4
O1i—Cu1—N189.38 (15)N2—C5—H5124.4
O1—Cu1—N1i89.38 (15)C7ii—C6—C8119.8 (5)
O1i—Cu1—N1i90.62 (15)C7ii—C6—H6120.1
N1—Cu1—N1i180.000 (1)C8—C6—H6120.1
C2—C1—H1A109.5C8—C7—C6ii120.6 (4)
C2—C1—H1B109.5C8—C7—H7119.7
H1A—C1—H1B109.5C6ii—C7—H7119.7
C2—C1—H1C109.5C7—C8—C6119.6 (4)
H1A—C1—H1C109.5C7—C8—N2120.6 (4)
H1B—C1—H1C109.5C6—C8—N2119.8 (4)
O2—C2—O1123.7 (5)C5—N1—C3105.6 (4)
O2—C2—C1120.9 (5)C5—N1—Cu1127.6 (3)
O1—C2—C1115.3 (5)C3—N1—Cu1126.6 (3)
C4—C3—N1109.9 (4)C5—N2—C4106.4 (4)
C4—C3—H3125.0C5—N2—C8126.7 (4)
N1—C3—H3125.0C4—N2—C8126.7 (4)
C3—C4—N2106.8 (4)C2—O1—Cu1116.1 (3)
C3—C4—H4126.6
N1—C3—C4—N20.0 (6)N1—C5—N2—C40.3 (6)
C6ii—C7—C8—C6−0.2 (9)N1—C5—N2—C8−176.4 (4)
C6ii—C7—C8—N2179.7 (5)C3—C4—N2—C5−0.2 (6)
C7ii—C6—C8—C70.2 (9)C3—C4—N2—C8176.5 (5)
C7ii—C6—C8—N2−179.7 (5)C7—C8—N2—C5−4.4 (7)
N2—C5—N1—C3−0.3 (6)C6—C8—N2—C5175.5 (5)
N2—C5—N1—Cu1175.0 (3)C7—C8—N2—C4179.6 (5)
C4—C3—N1—C50.1 (6)C6—C8—N2—C4−0.5 (7)
C4—C3—N1—Cu1−175.2 (4)O2—C2—O1—Cu14.9 (6)
O1—Cu1—N1—C51.0 (4)C1—C2—O1—Cu1−174.2 (4)
O1i—Cu1—N1—C5−179.0 (4)N1—Cu1—O1—C2−86.6 (3)
O1—Cu1—N1—C3175.3 (4)N1i—Cu1—O1—C293.4 (3)
O1i—Cu1—N1—C3−4.7 (4)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x−1, −y+1, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O20.851.942.792 (6)176
O1W—H1WB···O1Wiii0.902.312.807 (7)114
Symmetry code: (iii) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula[Cu(C2H3O2)2(C12H10N4)]·2H2O
Mr427.90
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)4.707 (2), 9.444 (3), 10.901 (5)
α, β, γ (°)72.569 (5), 82.956 (4), 76.766 (5)
V (Å3)449.3 (3)
Z1
Radiation typeMo Kα
µ (mm−1)1.26
Crystal size (mm)0.24 × 0.18 × 0.12
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.752, 0.864
No. of measured, independent and
observed [I > 2σ(I)] reflections		2248, 1562, 1530
Rint0.041
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.096, 1.06
No. of reflections1562
No. of parameters125
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.45, −0.40

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O20.851.942.792 (6)176.0
O1W—H1WB···O1Wi0.902.312.807 (7)114.00
Symmetry code: (i) −x+2, −y, −z+2.
 

Acknowledgements

This work was supported by the Construct Program of the Key Discipline of Hunan Province, the Hengyang Bureau of Science & Technology (grant No. 2009 K J29) and the Research Award Fund for Outstanding Young Teachers of Hunan Province (2008).

References

First citationBruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDong, H., Bi, W. & Zhu, H. (2009). Asian J. Chem. 21, 5598–5602.  CAS Google Scholar
 First citationHuang, X. C., Zhang, J. P., Lin, Y. Y., Yu, X. L. & Chen, X. M. (2004). Chem. Commun. pp. 1100–1101.  Web of Science CSD CrossRef Google Scholar
 First citationKitagawa, S. & Kondo, M. (1998). Bull. Chem. Soc. Jpn, 71, 1739–1753.  Web of Science CrossRef CAS Google Scholar
 First citationMasciocchi, N., Bruni, S., Cariati, E., Cariati, F., Galli, S. & Sironi, A. (2001). Inorg. Chem. 40, 5897–5905.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXie, J., Chen, X., Liu, G. X. & Sun, W. Y. (2007). Chin. J. Inorg. Chem. 23, 1295–1298.  CAS Google Scholar

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page m1482
https://doi.org/10.1107/S160053680904464X
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