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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 68| Part 9| September 2012| Page m1149
doi:10.1107/S1600536812033739

Di­aqua­bis­­(1H-imidazole-κN3)bis­­(4-nitro­benzoato-κO1)cadmium

Yan-Li Mao,a Xiao-Ke Yua and Jian-Li Lina*

aCenter of Applied Solid State Chemistry Research, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
*Correspondence e-mail: linjianli@nbu.edu.cn

(Received 8 July 2012; accepted 27 July 2012; online 4 August 2012)

In the centrosymmetric title compound, [Cd(C7H4NO4)2(C3H4N2)2(H2O)2], the CdII atom, located on an inversion center, is coordinated by two N atoms and four O atoms in an octa­hedral geometry. The inter­nal cohesion of the mol­ecule is enhanced by an intra­molecular O—H⋯O hydrogen bond. Inter­molecular O—H⋯O and C—H⋯O hydrogen bonds and π–π contacts [centroid–centroid distance = 3.6549 (2) Å] define two-dimensional networks parallel to (001), which are further connected by weaker C—H⋯O inter­actions into a weakly connected three-dimensional supra­molecular framework.

Related literature

For general background to aromatic carboxyl acid complexes, see: Kuang et al. (2007[Kuang, Y.-F., Li, C.-H., Li, W. & Yang, Y.-Q. (2007). Chin. J. Struct. Chem. 26, 749-752.]); Hsu et al. (2011[Hsu, S.-C., Lo, S.-H., Kao, C.-C. & Lin, C.-H. (2011). Acta Cryst. E67, m65.]). For related structures, see: Zheng et al. (2008[Zheng, Y.-Q., Cheng, D.-Y., Lin, J.-L., Li, Z.-F. & Wang, X.-W. (2008). Eur. J. Inorg. Chem. pp. 4453-4461.]).

[Scheme 1]

Experimental

Crystal data

  • [Cd(C7H4NO4)2(C3H4N2)2(H2O)2]

  • Mr = 614.80

  • Triclinic, [P \overline 1]

  • a = 5.8017 (12) Å

  • b = 8.0253 (16) Å

  • c = 12.879 (3) Å

  • α = 77.99 (3)°

  • β = 88.42 (3)°

  • γ = 85.16 (3)°

  • V = 584.4 (2) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.00 mm−1

  • T = 293 K

  • 0.33 × 0.14 × 0.09 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.989, Tmax = 0.989

  • 5719 measured reflections

  • 2627 independent reflections

  • 2511 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.076

  • S = 1.24

  • 2627 reflections

  • 175 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.80 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O5—H5A⋯O2 0.84 (1) 1.88 (1) 2.679 (1) 159
O5—H5B⋯O1i 0.84 (1) 1.97 (1) 2.785 (1) 164
C2—H2A⋯O5ii 0.93 2.58 3.244 (1) 129
C3—H3A⋯O5iii 0.93 2.43 3.344 (1) 169
C10—H10A⋯O2 0.93 2.42 2.751 (4) 101
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z; (iii) -x, -y+2, -z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812033739/bg2473sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033739/bg2473Isup2.hkl

checkCIF report


Comment top

Aromatic carboxyl acid complexes have been paid great attention these years for their potential applications in gas storage, separation, catalysis, magnetism, luminescence, and drug delivery (Kuang et al., 2007). As a N-containing aromatic carboxyl acid, nitrobenzoic acid has been widely used in dye intermediate, organic synthesis, sensitization material, functional pigment (Hsu et al., 2011). So far, to our knowledge, cadmium complexes constructed from 4-nitrobenzoato and imidazole have not been reported. In order to get new CdII complexes with novel functions and discover their structure-property relationship, a new complex [Cd(C7H4NO4)(C3H4N2)(H2O)] was synthesized.

The asymmetric unit of [Cd(C7H4NO4)(C3H4N2)(H2O)] consists of a Cd2+ ion lying on an inversion centre, a 4-NBA- ion (4-HNBA = 4-nitrobenzoic acid), one imidazole ligand and one lattice water as illustrated in Fig. 1. The Cd2+ cation is octahedrally coordinated by two N atoms of imidazole ligands, two O atoms from two 4-NBA- ions and two O atoms from two lattice water molecules; it takes a (4 + 2) octahedral geometry, with the oxygen atoms located in the equatorial plane (Cd—O1 = 2.364 (2) Å, Cd—O5 = 2.367 (2) Å, and the two nitrogen atoms occupying the axial position (Cd—N1 = 2.255 (2) Å). Table 1 presents the \p···\p contact information involving the C3N2 ring (centroid, Cg1) and Table 2, the more meaningful H-bonds in the structure; the most important ones are those involving water H's. The one described in the first entry in Table 2 is intramolecular; the seocnd one, instead defines chains along a (Figure 2, vertical arrays). The weak one involving C2—H2A (Table 2, third entry) and the π–π contact (Table 1) link chains into a two-dimensional supramolecular network parallel to (001) as illustrated in Figure 2. Finaly, the remaining weak H-bonds link these 2D structures into a 3D supramolecular architecture (Figure 3).

Related literature top

For general background to aromatic carboxyl acid complexes, see: Kuang et al. (2007); Hsu et al. (2011). For related structures, see: Zheng et al. (2008).

Experimental top

Dropwise addition of 1.0 ml (1 M) of K2CO3 to a stirred aqueous solution of Cd(CH3COO)2.2H2O (0.266 g, 1.0 mmol) in 10.0 ml of H2O yielded a fine white precipitate, which was separated by centrifugation and washed with water until no CH3COO- anions were detectable in the supernatant. The fresh precipitate was then added to a stirred aqueous solution of 4-nitrobenzoic acid (0.167 g, 1.0 mmol) in C2H5OH/H2O (1:1, 20.0 ml), producing a white suspension, to which imidazole (0.137 g, 2.0 mmol) was added. The mixture was further stirred vigorously for about 0.5 h. After filtration, the white filtrate (pH = 6.59) was maintained at room temperature and colorless crystals were grown.

Refinement top

H atoms bonded to C atoms were palced in geometrically calculated positions and were refined using a riding model. H atoms attached to O atoms were found in a difference Fourier synthesis and were refined with restrained O—H = 0.84 (1)Å. In all cases, Uiso(H) values were set at 1.2 Ueq(host).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Figure 1. ORTEP view of the title compound, The dispalcement ellipsoidsare drawn at 45% probability dispalcement ellipsoids. Symmetry code: (v)1-x, 2-y, -z.
[Figure 2] Fig. 2. The two-dimensional supramolecular networks parallel to (001). In order to observe how the complex moleculars form two-dimensional layers clearly, nitrobenzene on 4-nitrobenzoato molecules which are not engaged in link the components into a two-dimensional layers were omitted.
[Figure 3] Fig. 3. The three-dimensional framework of title complex.
Diaquabis(1H-imidazole-κN3)bis(4-nitrobenzoato- κO1)cadmium top
Crystal data top
[Cd(C7H4NO4)2(C3H4N2)2(H2O)2]Z = 1
Mr = 614.80F(000) = 308
Triclinic, P1Dx = 1.747 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8017 (12) ÅCell parameters from 5719 reflections
b = 8.0253 (16) Åθ = 3.2–27.5°
c = 12.879 (3) ŵ = 1.00 mm−1
α = 77.99 (3)°T = 293 K
β = 88.42 (3)°Plate, colorless
γ = 85.16 (3)°0.33 × 0.14 × 0.09 mm
V = 584.4 (2) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2627 independent reflections
Radiation source: fine-focus sealed tube2511 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −6→7
Tmin = 0.989, Tmax = 0.989k = −10→10
5719 measured reflectionsl = −16→16
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.24 w = 1/[σ2(Fo2) + (0.0208P)2 + 0.3927P]
where P = (Fo2 + 2Fc2)/3
2627 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.54 e Å−3
3 restraintsΔρmin = −0.80 e Å−3
Crystal data top
[Cd(C7H4NO4)2(C3H4N2)2(H2O)2]γ = 85.16 (3)°
Mr = 614.80V = 584.4 (2) Å3
Triclinic, P1Z = 1
a = 5.8017 (12) ÅMo Kα radiation
b = 8.0253 (16) ŵ = 1.00 mm−1
c = 12.879 (3) ÅT = 293 K
α = 77.99 (3)°0.33 × 0.14 × 0.09 mm
β = 88.42 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2627 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2511 reflections with I > 2σ(I)
Tmin = 0.989, Tmax = 0.989Rint = 0.031
5719 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0263 restraints
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.24Δρmax = 0.54 e Å−3
2627 reflectionsΔρmin = −0.80 e Å−3
175 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd0.50001.00000.00000.03040 (10)
N10.4161 (4)0.7310 (3)0.07261 (18)0.0351 (5)
C10.5412 (6)0.6131 (4)0.1376 (3)0.0497 (8)
H1A0.68440.62900.16320.060*
C20.2360 (6)0.4946 (4)0.1116 (3)0.0518 (8)
H2A0.12610.41600.11360.062*
N20.4388 (5)0.4676 (3)0.1627 (2)0.0500 (7)
C30.2227 (6)0.6573 (4)0.0569 (3)0.0510 (8)
H3A0.09920.71080.01470.061*
O10.7532 (3)0.9739 (3)0.14420 (15)0.0384 (5)
O20.4950 (4)1.0755 (3)0.25118 (18)0.0553 (6)
C40.6746 (5)0.9881 (4)0.2347 (2)0.0336 (6)
C50.8110 (5)0.8918 (4)0.3301 (2)0.0343 (6)
C61.0191 (5)0.7974 (4)0.3212 (2)0.0398 (7)
H6A1.07810.78930.25440.048*
C71.1397 (5)0.7150 (4)0.4110 (2)0.0451 (7)
H7A1.27980.65180.40540.054*
C81.0480 (5)0.7285 (4)0.5088 (2)0.0421 (7)
C90.8406 (6)0.8178 (5)0.5205 (3)0.0581 (10)
H9A0.78070.82350.58750.070*
C100.7234 (6)0.8990 (5)0.4301 (3)0.0568 (9)
H10A0.58210.96010.43650.068*
N31.1799 (5)0.6471 (4)0.6046 (2)0.0548 (7)
O31.3619 (6)0.5690 (5)0.5945 (3)0.1018 (13)
O41.1007 (6)0.6639 (5)0.6907 (2)0.0890 (10)
O50.1847 (3)1.1006 (3)0.09734 (16)0.0385 (5)
H5A0.252 (5)1.088 (4)0.1559 (14)0.046*
H5B0.069 (4)1.043 (4)0.112 (2)0.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd0.03111 (16)0.02902 (15)0.02818 (15)−0.00363 (11)−0.00305 (10)0.00151 (10)
N10.0371 (12)0.0309 (11)0.0343 (12)−0.0032 (10)−0.0033 (10)0.0009 (9)
C10.0417 (17)0.0403 (16)0.060 (2)−0.0052 (14)−0.0155 (15)0.0081 (14)
C20.057 (2)0.0329 (15)0.063 (2)−0.0156 (15)−0.0132 (17)0.0023 (14)
N20.0605 (17)0.0342 (13)0.0488 (16)−0.0008 (13)−0.0064 (13)0.0059 (11)
C30.0523 (19)0.0360 (15)0.061 (2)−0.0116 (15)−0.0226 (16)0.0051 (14)
O10.0343 (10)0.0508 (12)0.0283 (10)−0.0078 (9)−0.0042 (8)−0.0022 (8)
O20.0432 (12)0.0741 (16)0.0449 (13)0.0183 (12)−0.0127 (10)−0.0115 (11)
C40.0287 (13)0.0375 (14)0.0339 (14)−0.0045 (12)−0.0064 (11)−0.0045 (11)
C50.0330 (14)0.0394 (14)0.0291 (14)−0.0040 (12)−0.0038 (11)−0.0031 (11)
C60.0398 (15)0.0456 (16)0.0306 (14)0.0047 (13)−0.0003 (12)−0.0034 (12)
C70.0398 (16)0.0488 (17)0.0413 (17)0.0117 (14)−0.0032 (13)−0.0023 (13)
C80.0430 (16)0.0457 (16)0.0331 (15)−0.0038 (14)−0.0107 (12)0.0036 (12)
C90.052 (2)0.090 (3)0.0283 (16)0.0104 (19)0.0000 (14)−0.0078 (16)
C100.0446 (18)0.087 (3)0.0346 (17)0.0216 (18)−0.0033 (14)−0.0120 (16)
N30.0543 (18)0.0620 (18)0.0407 (16)−0.0015 (15)−0.0138 (13)0.0067 (13)
O30.079 (2)0.147 (3)0.0583 (19)0.052 (2)−0.0207 (16)0.0044 (19)
O40.090 (2)0.131 (3)0.0339 (15)0.017 (2)−0.0135 (14)0.0035 (16)
O50.0283 (10)0.0424 (11)0.0415 (12)−0.0039 (9)−0.0024 (8)−0.0005 (9)
Geometric parameters (Å, º) top
Cd—N1i2.254 (2)C4—C51.513 (4)
Cd—N12.254 (2)C5—C101.383 (4)
Cd—O1i2.364 (2)C5—C61.385 (4)
Cd—O12.364 (2)C6—C71.383 (4)
Cd—O5i2.370 (2)C6—H6A0.9300
Cd—O52.370 (2)C7—C81.375 (4)
N1—C11.308 (4)C7—H7A0.9300
N1—C31.351 (4)C8—C91.369 (5)
C1—N21.330 (4)C8—N31.471 (4)
C1—H1A0.9300C9—C101.377 (5)
C2—N21.343 (4)C9—H9A0.9300
C2—C31.345 (4)C10—H10A0.9300
C2—H2A0.9300N3—O31.199 (4)
C3—H3A0.9300N3—O41.218 (4)
O1—C41.263 (3)O5—H5A0.842 (10)
O2—C41.245 (4)O5—H5B0.842 (10)
Cg1···Cg1ii3.6549 (2)
N1i—Cd—N1180.0C4—O1—Cd120.39 (17)
N1i—Cd—O1i86.19 (8)O2—C4—O1125.1 (3)
N1—Cd—O1i93.81 (8)O2—C4—C5117.7 (3)
N1i—Cd—O193.81 (8)O1—C4—C5117.2 (2)
N1—Cd—O186.19 (8)C10—C5—C6118.9 (3)
O1i—Cd—O1180.0C10—C5—C4118.3 (3)
N1i—Cd—O5i88.39 (8)C6—C5—C4122.8 (3)
N1—Cd—O5i91.61 (8)C7—C6—C5120.5 (3)
O1i—Cd—O5i91.85 (7)C7—C6—H6A119.8
O1—Cd—O5i88.15 (7)C5—C6—H6A119.8
N1i—Cd—O591.61 (8)C8—C7—C6118.5 (3)
N1—Cd—O588.39 (8)C8—C7—H7A120.7
O1i—Cd—O588.15 (7)C6—C7—H7A120.7
O1—Cd—O591.85 (7)C9—C8—C7122.5 (3)
O5i—Cd—O5180.0C9—C8—N3118.7 (3)
C1—N1—C3105.2 (2)C7—C8—N3118.8 (3)
C1—N1—Cd128.3 (2)C8—C9—C10118.0 (3)
C3—N1—Cd126.52 (19)C8—C9—H9A121.0
N1—C1—N2111.8 (3)C10—C9—H9A121.0
N1—C1—H1A124.1C9—C10—C5121.5 (3)
N2—C1—H1A124.1C9—C10—H10A119.2
N2—C2—C3106.7 (3)C5—C10—H10A119.2
N2—C2—H2A126.6O3—N3—O4122.8 (3)
C3—C2—H2A126.6O3—N3—C8118.8 (3)
C1—N2—C2106.7 (3)O4—N3—C8118.4 (3)
C2—C3—N1109.6 (3)Cd—O5—H5A98 (2)
C2—C3—H3A125.2Cd—O5—H5B120 (2)
N1—C3—H3A125.2H5A—O5—H5B104 (2)
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O20.84 (1)1.88 (1)2.679 (1)159
O5—H5B···O1iii0.84 (1)1.97 (1)2.785 (1)164
C2—H2A···O5iv0.932.583.244 (1)129
C3—H3A···O5v0.932.433.344 (1)169
C10—H10A···O20.932.422.751 (4)101
Symmetry codes: (iii) x−1, y, z; (iv) x, y−1, z; (v) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula[Cd(C7H4NO4)2(C3H4N2)2(H2O)2]
Mr614.80
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.8017 (12), 8.0253 (16), 12.879 (3)
α, β, γ (°)77.99 (3), 88.42 (3), 85.16 (3)
V (Å3)584.4 (2)
Z1
Radiation typeMo Kα
µ (mm−1)1.00
Crystal size (mm)0.33 × 0.14 × 0.09
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.989, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		5719, 2627, 2511
Rint0.031
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.076, 1.24
No. of reflections2627
No. of parameters175
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.54, −0.80

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O20.84 (1)1.88 (1)2.679 (1)159.0
O5—H5B···O1i0.84 (1)1.97 (1)2.785 (1)164.0
C2—H2A···O5ii0.932.583.244 (1)129.0
C3—H3A···O5iii0.932.433.344 (1)169.0
C10—H10A···O20.932.422.751 (4)101.0
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) −x, −y+2, −z.
 

Acknowledgements

This project was supported by the Scientific Research Fund of Ningbo University (grant No. XKL069). Sincere thanks are also extended to the K. C. Wong Magna Fund in Ningbo University.

References

First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationHsu, S.-C., Lo, S.-H., Kao, C.-C. & Lin, C.-H. (2011). Acta Cryst. E67, m65.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationKuang, Y.-F., Li, C.-H., Li, W. & Yang, Y.-Q. (2007). Chin. J. Struct. Chem. 26, 749–752.  CAS Google Scholar
 First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZheng, Y.-Q., Cheng, D.-Y., Lin, J.-L., Li, Z.-F. & Wang, X.-W. (2008). Eur. J. Inorg. Chem. pp. 4453–4461.  Web of Science CSD CrossRef 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 68| Part 9| September 2012| Page m1149
doi:10.1107/S1600536812033739
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