PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m794.
Published online 2010 June 16. doi:  10.1107/S1600536810022117
PMCID: PMC3006711

catena-Poly[[aqua­(imidazole)­cadmium(II)]-μ3-benzene-1,3-dicarboxyl­ato]

Abstract

In the title compound, [Cd(C8H4O4)(C3H4N2)(H2O)]n, the CdII ion is seven-coordinated by five O atoms from three crystallographically independent benzene-1,3-carboxylate ligands, one N atom from the imidazole ligand and one coordinated water mol­ecule. Neighboring CdII ions are bridged by the benzene-1,3-dicarboxyl­ate ligands, forming a zigzag polymeric chain structure. These chains are further extended into a three-dimensional supra­molecular structure through O—H(...)O and N—H(...)O hydrogen bonds.

Related literature

For the synthesis, see: Yaghi et al. (1998 [triangle]). For related structures, see: Ma et al. (2008 [triangle]); Wang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m794-scheme1.jpg

Experimental

Crystal data

  • [Cd(C8H4O4)(C3H4N2)(H2O)]
  • M r = 362.61
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m794-efi1.jpg
  • a = 8.2616 (8) Å
  • b = 8.3138 (8) Å
  • c = 10.235 (1) Å
  • α = 67.017 (2)°
  • β = 68.176 (2)°
  • γ = 81.054 (2)°
  • V = 600.76 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.84 mm−1
  • T = 293 K
  • 0.27 × 0.18 × 0.06 mm

Data collection

  • Bruker APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.536, T max = 1.000
  • 3166 measured reflections
  • 2086 independent reflections
  • 2049 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.072
  • S = 1.15
  • 2086 reflections
  • 184 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.79 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022117/lx2148sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022117/lx2148Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (20971122) and the State Key Laboratory of Structural Chemistry for financial support.

supplementary crystallographic information

Comment

In recent years, considerable effort was paied in the study of metal-organic hybrid materials with the extended supermolecular framework structures, owing to their intriguing network topologies and potential application in adsorption, molecular recognition, catalysis and maganetism (Yaghi et al., 1998 ). Currently, carboxylic acids have been widely used as polydentate and bridging ligands since they can bind metal ions in diverse modes and play an important role in adjusting verious topologies structures. A number of promising supramolecular complexes have been designed and constructed by using carboxylic acids as favorable conditions. (Ma et al., 2008; Wang et al., 2008). In this paper, we report the synthesis and structural characterzation of the title compound in which the isophthalic acid ligand displayed its good coordination ability and diverse coordination modes.

The CdII ion is six-coordinated by four O atoms from three crystallographically independent benzene-1,3- dicarboxylate ligands and one N atom from the chelating imidazole ligand and one coordinated water molecule (Fig. 1 & Table 1). The neighboring Cdi ion is bridged by the benzene-1, 3-dicarboxylate ligands to form a one-dimensional chain structure. In the crystal structure, the adjacent chains are linked via O–H···O and N–H···O hydrogen bonds (Fig. 2 & Table 2) resulting in the formation of a three dimensional supramolecular structure.

Experimental

A 10 ml aqueous solution of imidazole (0.014 g, 0.20 mmol) and isophthalic acid (0.034 g,0.020 mmol) was slowly added into cadmium nitrate (0.062 g, 0.20 mmol) solution in methanol (10 ml), and the mixed solution was stirred for 20 min and then was heated in a 30 ml Teflon-line autoclave under autogeneous pressure at 423 K for 3 d. After cooling to room temperature, colorless block crystals were obtained. (yield 38%).

Refinement

H atoms bound to H2O and NH atoms were located in a difference map and refined freely. Other H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. [Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x, -y+1, -z+1; (iii) x, y, z+1.]
Fig. 2.
The crystal packing of (I), showing one layer of molecules connected by O–H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted. [Symmetry codes: (i) x, y-1 , z; (ii) x, y-1, z+1; ...

Crystal data

[Cd(C8H4O4)(C3H4N2)(H2O)]Z = 2
Mr = 362.61F(000) = 356
Triclinic, P1Dx = 2.005 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2616 (8) ÅCell parameters from 3126 reflections
b = 8.3138 (8) Åθ = 3.3–27.5°
c = 10.235 (1) ŵ = 1.84 mm1
α = 67.017 (2)°T = 293 K
β = 68.176 (2)°Block, yellow
γ = 81.054 (2)°0.27 × 0.18 × 0.06 mm
V = 600.76 (10) Å3

Data collection

Bruker APEX CCD diffractometer2086 independent reflections
Radiation source: fine-focus sealed tube2049 reflections with I > 2σ(I)
graphiteRint = 0.019
Detector resolution: 10 pixels mm-1θmax = 25.0°, θmin = 2.3°
ω scansh = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −9→4
Tmin = 0.536, Tmax = 1.000l = −12→11
3166 measured reflections

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)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.15w = 1/[σ2(Fo2) + (0.0315P)2 + 1.1125P] where P = (Fo2 + 2Fc2)/3
2086 reflections(Δ/σ)max < 0.001
184 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.79 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cd10.08672 (3)0.32297 (3)0.90289 (3)0.02898 (11)
O1−0.0532 (4)0.6070 (4)0.8593 (3)0.0337 (6)
O20.0672 (4)0.8334 (4)0.8475 (3)0.0382 (6)
O30.1082 (4)0.7617 (4)0.1628 (3)0.0347 (6)
O4−0.1232 (4)0.6718 (4)0.3685 (3)0.0405 (7)
O50.2389 (4)0.0533 (4)0.9029 (4)0.0414 (7)
H5A0.209 (10)0.017 (10)0.849 (9)0.10 (2)*
H5B0.211 (10)−0.024 (10)0.994 (9)0.10 (3)*
N10.3422 (4)0.4507 (4)0.8114 (4)0.0340 (7)
N20.5999 (5)0.5524 (5)0.6516 (4)0.0453 (9)
H20.687 (9)0.587 (9)0.570 (8)0.08 (2)*
C10.0393 (5)0.7429 (5)0.7840 (4)0.0272 (7)
C20.1174 (5)0.7962 (5)0.6165 (4)0.0255 (7)
C30.2660 (5)0.8979 (5)0.5366 (4)0.0325 (8)
H30.31530.93720.58680.039*
C40.3406 (5)0.9406 (6)0.3814 (5)0.0398 (9)
H40.44281.00480.32840.048*
C50.2642 (5)0.8885 (5)0.3047 (4)0.0333 (8)
H50.31450.91840.20060.040*
C80.0251 (5)0.7384 (5)0.3016 (4)0.0293 (8)
C70.0420 (4)0.7439 (4)0.5394 (4)0.0248 (7)
H7−0.05750.67570.59300.030*
C110.4652 (6)0.4570 (6)0.6844 (5)0.0425 (10)
H110.45920.40100.62350.051*
C100.4032 (6)0.5481 (6)0.8641 (5)0.0436 (10)
H100.34410.56880.95320.052*
C90.5632 (6)0.6097 (7)0.7663 (6)0.0488 (11)
H90.63380.67790.77620.059*
C60.1121 (5)0.7914 (5)0.3837 (4)0.0261 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.03179 (17)0.03293 (17)0.02429 (16)−0.01047 (11)−0.00754 (11)−0.01069 (12)
O10.0381 (15)0.0359 (15)0.0243 (13)−0.0070 (12)−0.0089 (11)−0.0074 (11)
O20.0528 (17)0.0447 (16)0.0260 (13)−0.0095 (13)−0.0144 (12)−0.0175 (12)
O30.0442 (15)0.0420 (15)0.0236 (13)−0.0069 (12)−0.0114 (11)−0.0154 (11)
O40.0422 (16)0.0530 (18)0.0302 (14)−0.0195 (13)−0.0118 (12)−0.0125 (13)
O50.0440 (17)0.0385 (16)0.0405 (17)−0.0083 (13)−0.0105 (14)−0.0137 (15)
N10.0310 (16)0.0374 (18)0.0328 (17)−0.0080 (13)−0.0085 (13)−0.0114 (14)
N20.0336 (19)0.055 (2)0.039 (2)−0.0110 (17)−0.0046 (16)−0.0120 (18)
C10.0274 (18)0.0310 (19)0.0236 (17)−0.0004 (14)−0.0103 (14)−0.0091 (15)
C20.0289 (18)0.0254 (17)0.0223 (17)−0.0011 (14)−0.0100 (14)−0.0073 (14)
C30.036 (2)0.042 (2)0.0276 (19)−0.0122 (16)−0.0133 (16)−0.0137 (16)
C40.033 (2)0.053 (3)0.032 (2)−0.0214 (18)−0.0048 (16)−0.0118 (18)
C50.035 (2)0.042 (2)0.0202 (17)−0.0076 (16)−0.0060 (15)−0.0092 (16)
C80.038 (2)0.0273 (18)0.0267 (18)−0.0028 (15)−0.0152 (16)−0.0089 (15)
C70.0250 (17)0.0278 (17)0.0220 (17)−0.0045 (13)−0.0084 (13)−0.0075 (14)
C110.040 (2)0.050 (3)0.040 (2)−0.0124 (19)−0.0100 (18)−0.017 (2)
C100.036 (2)0.057 (3)0.042 (2)−0.0128 (19)−0.0100 (18)−0.021 (2)
C90.040 (2)0.057 (3)0.054 (3)−0.017 (2)−0.015 (2)−0.020 (2)
C60.0285 (18)0.0281 (18)0.0248 (17)−0.0013 (14)−0.0113 (14)−0.0105 (14)

Geometric parameters (Å, °)

Cd1—N12.216 (3)N2—H20.85 (7)
Cd1—O3i2.251 (3)C1—C21.492 (5)
Cd1—O2ii2.311 (3)C2—C71.384 (5)
Cd1—O52.394 (3)C2—C31.388 (5)
Cd1—O12.413 (3)C3—C41.389 (5)
Cd1—O1ii2.626 (3)C3—H30.9300
Cd1—O4i2.663 (3)C4—C51.387 (6)
O1—C11.266 (5)C4—H40.9300
O2—C11.260 (4)C5—C61.391 (5)
O3—C81.276 (4)C5—H50.9300
O4—C81.252 (5)C8—C61.501 (5)
O5—H5A0.84 (8)C7—C61.387 (5)
O5—H5B0.87 (8)C7—H70.9300
N1—C111.306 (5)C11—H110.9300
N1—C101.368 (5)C10—C91.356 (6)
N2—C111.330 (6)C10—H100.9300
N2—C91.351 (6)C9—H90.9300
N1—Cd1—O3i143.34 (11)C9—N2—H2124 (4)
N1—Cd1—O2ii127.43 (11)O2—C1—O1121.5 (3)
O3i—Cd1—O2ii88.49 (10)O2—C1—C2119.4 (3)
N1—Cd1—O588.63 (11)O1—C1—C2119.1 (3)
O3i—Cd1—O587.33 (11)C7—C2—C3119.4 (3)
O2ii—Cd1—O585.20 (11)C7—C2—C1120.0 (3)
N1—Cd1—O189.20 (11)C3—C2—C1120.5 (3)
O3i—Cd1—O189.03 (10)C2—C3—C4119.7 (3)
O2ii—Cd1—O1103.25 (10)C2—C3—H3120.2
O5—Cd1—O1170.71 (11)C4—C3—H3120.2
N1—Cd1—O1ii83.08 (10)C5—C4—C3120.6 (4)
O3i—Cd1—O1ii131.61 (9)C5—C4—H4119.7
O2ii—Cd1—O1ii52.58 (9)C3—C4—H4119.7
O5—Cd1—O1ii112.79 (11)C4—C5—C6119.8 (3)
O1—Cd1—O1ii75.89 (9)C4—C5—H5120.1
N1—Cd1—O4i91.00 (10)C6—C5—H5120.1
O3i—Cd1—O4i52.54 (9)O4—C8—O3121.5 (3)
O2ii—Cd1—O4i137.72 (9)O4—C8—C6120.7 (3)
O5—Cd1—O4i78.09 (11)O3—C8—C6117.8 (3)
O1—Cd1—O4i92.92 (9)C2—C7—C6121.2 (3)
O1ii—Cd1—O4i167.35 (9)C2—C7—H7119.4
C1—O1—Cd1119.5 (2)C6—C7—H7119.4
C1—O1—Cd1ii85.5 (2)N1—C11—N2112.7 (4)
Cd1—O1—Cd1ii104.11 (9)N1—C11—H11123.7
C1—O2—Cd1ii100.4 (2)N2—C11—H11123.7
C8—O3—Cd1i102.2 (2)C9—C10—N1109.4 (4)
Cd1—O5—H5A108 (5)C9—C10—H10125.3
Cd1—O5—H5B110 (5)N1—C10—H10125.3
H5A—O5—H5B109 (7)N2—C9—C10106.5 (4)
C11—N1—C10104.7 (3)N2—C9—H9126.7
C11—N1—Cd1125.3 (3)C10—C9—H9126.7
C10—N1—Cd1129.8 (3)C7—C6—C5119.1 (3)
C11—N2—C9106.7 (4)C7—C6—C8120.4 (3)
C11—N2—H2129 (4)C5—C6—C8120.4 (3)
N1—Cd1—O1—C19.8 (3)O2—C1—C2—C7−156.1 (3)
O3i—Cd1—O1—C1−133.6 (3)O1—C1—C2—C724.1 (5)
O2ii—Cd1—O1—C1138.2 (3)O2—C1—C2—C324.1 (5)
O1ii—Cd1—O1—C192.8 (3)O1—C1—C2—C3−155.6 (4)
O4i—Cd1—O1—C1−81.2 (3)C7—C2—C3—C4−2.3 (6)
N1—Cd1—O1—Cd1ii−83.06 (11)C1—C2—C3—C4177.5 (4)
O3i—Cd1—O1—Cd1ii133.56 (10)C2—C3—C4—C52.6 (7)
O2ii—Cd1—O1—Cd1ii45.34 (11)C3—C4—C5—C6−0.5 (7)
O1ii—Cd1—O1—Cd1ii0.0Cd1i—O3—C8—O44.2 (4)
O4i—Cd1—O1—Cd1ii−174.03 (9)Cd1i—O3—C8—C6−176.6 (3)
O3i—Cd1—N1—C11−24.3 (5)C3—C2—C7—C6−0.1 (5)
O2ii—Cd1—N1—C11142.2 (3)C1—C2—C7—C6−179.9 (3)
O5—Cd1—N1—C1159.3 (4)C10—N1—C11—N2−0.4 (5)
O1—Cd1—N1—C11−111.6 (4)Cd1—N1—C11—N2175.6 (3)
O1ii—Cd1—N1—C11172.5 (4)C9—N2—C11—N11.0 (6)
O4i—Cd1—N1—C11−18.7 (4)C11—N1—C10—C9−0.4 (5)
O3i—Cd1—N1—C10150.6 (3)Cd1—N1—C10—C9−176.1 (3)
O2ii—Cd1—N1—C10−42.9 (4)C11—N2—C9—C10−1.2 (5)
O5—Cd1—N1—C10−125.8 (4)N1—C10—C9—N20.9 (6)
O1—Cd1—N1—C1063.3 (4)C2—C7—C6—C52.1 (5)
O1ii—Cd1—N1—C10−12.6 (4)C2—C7—C6—C8−178.0 (3)
O4i—Cd1—N1—C10156.2 (4)C4—C5—C6—C7−1.8 (6)
Cd1ii—O2—C1—O10.1 (4)C4—C5—C6—C8178.3 (4)
Cd1ii—O2—C1—C2−179.6 (3)O4—C8—C6—C79.7 (5)
Cd1—O1—C1—O2−103.8 (4)O3—C8—C6—C7−169.4 (3)
Cd1ii—O1—C1—O2−0.1 (3)O4—C8—C6—C5−170.4 (4)
Cd1—O1—C1—C276.0 (4)O3—C8—C6—C510.4 (5)
Cd1ii—O1—C1—C2179.6 (3)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5A···O2iii0.84 (8)2.07 (8)2.809 (4)146 (7)
O5—H5B···O3iv0.87 (8)1.96 (8)2.786 (4)158 (7)
N2—H2···O4v0.85 (7)2.00 (7)2.854 (5)175 (6)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2148).

References

  • Ma, S., Sun, D., Simmons, J. M., Collier, C. D., Yuan, D. & Zhou, H. C. (2008). J. Am. Chem. Soc.130, 1012-1016. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Simemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Wang, J., Lin, Z., Ou, Y. C., Yang, N. L., Zhang, Y. H. & Tong, M. L. (2008). Inorg. Chem.47, 190–199. [PubMed]
  • Yaghi, O. M., Li, H., Davis, C., Richardson, D. & Groy, T. L. (1998). Acc. Chem. Res.31, 474–484.

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