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Acta Cryst. (2008). E64, m653    [ doi:10.1107/S1600536808009409 ]

Bis(1H-imidazole-[kappa]N3)bis(1-naphthaleneacetato-[kappa]2O,O')cadmium(II)

W.-D. Song, L.-L. Ji and H.-M. Wu

Abstract top

In the mononuclear title compound, [Cd(C12H9O2)2(C3H4N2)2], the CdII centre has a distorted octahedral coordination geometry defined by four O atoms from two naphthaleneacetate ligands and two N atoms from two imidazole ligands. The molecules are linked by N-H...O hydrogen bonds, forming a layer network.

Comment top

naphthaleneacetate is nice ligand which has versatile bonding modes to metal ions and easily forms simple complexes (Liu et al., 2006; Duan et al., 2007). Recently, we obtained the mononuclear cadmium complex, (I), its crystal structure is reported here. Recently, we obtained the title novel mononuclear complex (I), by the reaction of cadmium chloride, 1-naphthylacetic acid and imidazole in an aqueous solution, and its crystal structure is reported here.

As depicted in Fig. 1, the CdII centre in (I) presents a distorted octahedral coordination geometry, defined by four O atoms from two 1-naphthaleneacetate ligands, and two N atoms from two imidazole ligands. The structural packing is governed by N—H···o hydrogen bonding interaction (Table 1) to form a layered network (Fig. 2).

Related literature top

For related literature, see: Duan et al. (2007); Liu et al. (2006).

Experimental top

The title complex was prepared by the addition of a stoichiometric amount of cadmium chloride (1 mmol) and imidazole (1 mmol) to a hot aqueous solution(10 ml) of 1-naphthylacetic acid (1 mmol). the pH was then adjusted to 7.0 to 8.0 with NaOH (1 mmol). The resulting solution was filtered, and colorlee single crystals were obtained at room temperature over several days.

Refinement top

All H-atoms were placed in calculated positions with C—H = 0.93–0.97 Å, N—H = 0.86 Å; refined using a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C, N).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atomic numbering scheme. Non-H atoms are shown as 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The packing of structure (I).
Bis(1H-imidazole-κN3)bis(1-naphthaleneacetato- κ2O,O')cadmium(II) top
Crystal data top
[Cd(C12H9O2)2(C3H4N2)2]F000 = 1256
Mr = 618.95Dx = 1.496 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5300 reflections
a = 8.5275 (3) Åθ = 1.3–28.0º
b = 17.1596 (7) ŵ = 0.84 mm−1
c = 19.1198 (6) ÅT = 296 (2) K
β = 100.735 (2)ºBlock, colorless
V = 2748.81 (17) Å30.26 × 0.23 × 0.21 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer		5399 independent reflections
Radiation source: fine-focus sealed tube3336 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.089
T = 296(2) Kθmax = 26.0º
φ and ω scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→10
Tmin = 0.812, Tmax = 0.844k = −16→21
26061 measured reflectionsl = −23→23
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.143  w = 1/[σ2(Fo2) + (0.0533P)2 + 1.0058P]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
5399 reflectionsΔρmax = 0.57 e Å−3
340 parametersΔρmin = −1.16 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cd(C12H9O2)2(C3H4N2)2]V = 2748.81 (17) Å3
Mr = 618.95Z = 4
Monoclinic, P21/nMo Kα
a = 8.5275 (3) ŵ = 0.84 mm−1
b = 17.1596 (7) ÅT = 296 (2) K
c = 19.1198 (6) Å0.26 × 0.23 × 0.21 mm
β = 100.735 (2)º
Data collection top
Bruker APEXII area-detector
diffractometer		5399 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3336 reflections with I > 2σ(I)
Tmin = 0.812, Tmax = 0.844Rint = 0.089
26061 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051340 parameters
wR(F2) = 0.143H-atom parameters constrained
S = 0.99Δρmax = 0.57 e Å−3
5399 reflectionsΔρmin = −1.16 e Å−3
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
C10.3023 (7)0.6405 (3)0.3585 (3)0.0583 (14)
C20.3810 (7)0.6218 (4)0.4342 (3)0.0694 (16)
H2A0.34500.65940.46560.083*
H2B0.34490.57080.44630.083*
C30.5602 (7)0.6219 (3)0.4484 (2)0.0581 (14)
C40.6434 (8)0.6822 (3)0.4844 (3)0.0656 (16)
H40.58780.72240.50160.079*
C50.8115 (8)0.6849 (3)0.4962 (3)0.0639 (15)
H50.86520.72650.52120.077*
C60.8959 (7)0.6271 (3)0.4713 (2)0.0595 (14)
H61.00670.62970.47900.071*
C70.8159 (7)0.5633 (3)0.4339 (2)0.0540 (13)
C80.9015 (7)0.5033 (4)0.4069 (3)0.0649 (15)
H81.01240.50520.41450.078*
C90.8232 (9)0.4431 (4)0.3701 (3)0.0785 (18)
H90.88020.40380.35250.094*
C100.6560 (9)0.4402 (4)0.3585 (4)0.088 (2)
H100.60250.39910.33260.105*
C110.5716 (7)0.4966 (4)0.3845 (3)0.0716 (16)
H110.46090.49270.37710.086*
C120.6464 (6)0.5606 (3)0.4223 (2)0.0543 (13)
C130.2197 (7)0.6142 (3)0.1108 (2)0.0593 (14)
C140.2727 (9)0.5800 (4)0.0458 (3)0.0794 (19)
H14A0.19110.59180.00460.095*
H14B0.36910.60700.03940.095*
C150.3051 (9)0.4945 (4)0.0457 (3)0.0718 (17)
C160.2010 (9)0.4454 (4)0.0041 (3)0.092 (2)
H160.10810.4658−0.02300.111*
C170.2301 (11)0.3654 (5)0.0011 (4)0.101 (3)
H170.15590.3335−0.02720.121*
C180.3651 (12)0.3339 (5)0.0390 (5)0.102 (3)
H180.38320.28060.03610.122*
C190.4786 (9)0.3811 (4)0.0827 (3)0.0738 (18)
C200.6198 (11)0.3493 (5)0.1221 (4)0.091 (2)
H200.63940.29620.11920.109*
C210.7265 (12)0.3946 (6)0.1637 (4)0.113 (3)
H210.81920.37300.18980.135*
C220.6983 (11)0.4739 (6)0.1678 (4)0.108 (3)
H220.77310.50480.19680.129*
C230.5650 (10)0.5074 (4)0.1308 (3)0.085 (2)
H230.55020.56080.13480.102*
C240.4467 (9)0.4625 (3)0.0858 (3)0.0684 (18)
C25−0.1907 (7)0.6672 (3)0.2707 (3)0.0589 (14)
H25−0.13940.64070.31100.071*
C26−0.2362 (7)0.7286 (3)0.1729 (3)0.0626 (15)
H26−0.22100.75360.13150.075*
C27−0.3772 (8)0.7215 (4)0.1936 (3)0.0734 (16)
H27−0.47580.73940.16990.088*
C280.2489 (10)0.8574 (4)0.2921 (3)0.099 (3)
H280.23260.83980.33620.118*
C290.2722 (7)0.8611 (3)0.1845 (3)0.0635 (15)
H290.27230.84660.13760.076*
C300.3157 (7)0.9321 (4)0.2124 (3)0.0698 (16)
H300.35210.97430.18940.084*
Cd10.14721 (4)0.68863 (2)0.227269 (18)0.05146 (17)
N10.2286 (6)0.8142 (2)0.2344 (2)0.0604 (12)
N20.2951 (7)0.9287 (3)0.2801 (3)0.0800 (15)
H20.30950.96640.31030.096*
N3−0.1180 (5)0.6943 (2)0.2210 (2)0.0542 (11)
N4−0.3455 (6)0.6822 (3)0.2569 (3)0.0648 (13)
H4A−0.41370.66970.28290.078*
O10.1546 (5)0.6372 (3)0.3436 (2)0.0823 (9)
O20.3806 (5)0.6581 (3)0.3125 (2)0.0823 (9)
O30.2221 (6)0.6855 (2)0.1175 (2)0.0803 (9)
O40.1694 (6)0.5712 (2)0.1548 (2)0.0803 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.051 (4)0.061 (4)0.066 (3)0.015 (3)0.019 (3)0.004 (3)
C20.059 (4)0.093 (5)0.059 (3)0.003 (3)0.016 (3)0.003 (3)
C30.056 (4)0.074 (4)0.044 (3)0.010 (3)0.009 (3)0.005 (3)
C40.073 (5)0.074 (4)0.048 (3)0.014 (3)0.006 (3)−0.005 (3)
C50.076 (5)0.064 (4)0.048 (3)−0.007 (3)0.001 (3)0.000 (3)
C60.054 (4)0.064 (4)0.057 (3)−0.002 (3)0.001 (3)0.007 (3)
C70.056 (4)0.062 (3)0.043 (2)0.004 (3)0.005 (2)0.012 (2)
C80.054 (4)0.070 (4)0.068 (3)0.011 (3)0.004 (3)0.002 (3)
C90.076 (5)0.069 (4)0.089 (4)0.020 (4)0.012 (4)−0.002 (3)
C100.088 (6)0.067 (4)0.101 (5)0.003 (4)0.002 (4)−0.019 (4)
C110.054 (4)0.075 (4)0.081 (4)−0.005 (3)−0.001 (3)−0.004 (3)
C120.050 (3)0.061 (3)0.051 (3)0.002 (3)0.006 (3)0.005 (2)
C130.070 (4)0.060 (4)0.050 (3)0.011 (3)0.017 (3)0.009 (2)
C140.109 (6)0.077 (4)0.061 (3)0.011 (4)0.036 (4)0.007 (3)
C150.092 (5)0.078 (4)0.053 (3)0.004 (4)0.034 (3)−0.011 (3)
C160.095 (6)0.103 (6)0.084 (4)0.011 (5)0.030 (4)−0.037 (4)
C170.092 (6)0.097 (6)0.121 (6)−0.013 (5)0.038 (5)−0.055 (5)
C180.118 (7)0.078 (5)0.130 (6)−0.013 (5)0.076 (6)−0.036 (5)
C190.098 (6)0.061 (4)0.072 (4)0.002 (4)0.041 (4)−0.009 (3)
C200.127 (7)0.072 (5)0.081 (4)0.014 (5)0.040 (5)0.002 (4)
C210.145 (9)0.113 (7)0.080 (5)0.028 (6)0.019 (5)0.005 (5)
C220.122 (8)0.106 (7)0.091 (5)−0.014 (6)0.007 (5)−0.020 (5)
C230.120 (7)0.065 (4)0.074 (4)−0.007 (5)0.027 (4)−0.002 (4)
C240.104 (5)0.057 (4)0.055 (3)−0.010 (4)0.043 (4)−0.007 (3)
C250.046 (3)0.070 (4)0.063 (3)0.003 (3)0.014 (3)0.011 (3)
C260.072 (4)0.058 (3)0.057 (3)0.005 (3)0.011 (3)0.008 (3)
C270.056 (4)0.079 (4)0.080 (4)−0.002 (3)0.002 (3)0.004 (4)
C280.166 (8)0.062 (4)0.088 (4)−0.022 (4)0.077 (5)−0.009 (3)
C290.082 (4)0.052 (4)0.058 (3)0.002 (3)0.019 (3)0.004 (3)
C300.079 (5)0.059 (4)0.076 (4)0.003 (3)0.028 (3)0.010 (3)
Cd10.0507 (3)0.0500 (3)0.0565 (2)−0.00004 (18)0.01726 (19)0.00188 (17)
N10.067 (3)0.054 (3)0.066 (3)−0.004 (2)0.029 (2)−0.008 (2)
N20.106 (4)0.050 (3)0.094 (3)−0.017 (3)0.045 (3)−0.014 (3)
N30.048 (3)0.058 (3)0.059 (2)0.004 (2)0.017 (2)0.009 (2)
N40.053 (3)0.071 (3)0.074 (3)−0.003 (2)0.023 (2)0.005 (2)
O10.0491 (18)0.123 (3)0.0752 (18)0.0087 (18)0.0131 (15)0.0229 (18)
O20.0491 (18)0.123 (3)0.0752 (18)0.0087 (18)0.0131 (15)0.0229 (18)
O30.125 (3)0.0522 (18)0.0756 (17)0.0066 (17)0.0499 (18)0.0068 (14)
O40.125 (3)0.0522 (18)0.0756 (17)0.0066 (17)0.0499 (18)0.0068 (14)
Geometric parameters (Å, °) top
C1—O21.236 (6)C18—C191.412 (10)
C1—O11.240 (6)C18—H180.9300
C1—C21.513 (7)C19—C201.407 (9)
C2—C31.501 (8)C19—C241.426 (8)
C2—H2A0.9700C20—C211.340 (11)
C2—H2B0.9700C20—H200.9300
C3—C41.366 (8)C21—C221.386 (11)
C3—C121.425 (7)C21—H210.9300
C4—C51.410 (9)C22—C231.350 (10)
C4—H40.9300C22—H220.9300
C5—C61.362 (7)C23—C241.423 (9)
C5—H50.9300C23—H230.9300
C6—C71.413 (7)C25—N31.313 (6)
C6—H60.9300C25—N41.323 (7)
C7—C81.414 (7)C25—H250.9300
C7—C121.422 (7)C26—C271.340 (8)
C8—C91.354 (8)C26—N31.365 (7)
C8—H80.9300C26—H260.9300
C9—C101.402 (9)C27—N41.367 (8)
C9—H90.9300C27—H270.9300
C10—C111.356 (8)C28—N11.315 (7)
C10—H100.9300C28—N21.319 (7)
C11—C121.402 (7)C28—H280.9300
C11—H110.9300C29—N11.352 (6)
C13—O31.230 (6)C29—C301.355 (7)
C13—O41.252 (6)C29—H290.9300
C13—C141.517 (7)C30—N21.339 (7)
C14—C151.494 (8)C30—H300.9300
C14—H14A0.9700Cd1—N32.244 (4)
C14—H14B0.9700Cd1—N12.259 (4)
C15—C161.367 (9)Cd1—O32.306 (3)
C15—C241.415 (9)Cd1—O12.384 (4)
C16—C171.398 (10)Cd1—O22.384 (4)
C16—H160.9300Cd1—O42.473 (4)
C17—C181.353 (11)N2—H20.8600
C17—H170.9300N4—H4A0.8600
O2—C1—O1120.6 (5)C21—C20—H20119.6
O2—C1—C2122.0 (5)C19—C20—H20119.6
O1—C1—C2117.4 (4)C20—C21—C22119.8 (9)
C3—C2—C1115.3 (4)C20—C21—H21120.1
C3—C2—H2A108.4C22—C21—H21120.1
C1—C2—H2A108.4C23—C22—C21121.7 (8)
C3—C2—H2B108.4C23—C22—H22119.1
C1—C2—H2B108.4C21—C22—H22119.1
H2A—C2—H2B107.5C22—C23—C24121.3 (7)
C4—C3—C12118.8 (5)C22—C23—H23119.4
C4—C3—C2120.5 (5)C24—C23—H23119.4
C12—C3—C2120.6 (5)C15—C24—C23123.8 (6)
C3—C4—C5121.5 (5)C15—C24—C19120.4 (6)
C3—C4—H4119.3C23—C24—C19115.8 (7)
C5—C4—H4119.3N3—C25—N4112.0 (5)
C6—C5—C4120.5 (5)N3—C25—H25124.0
C6—C5—H5119.7N4—C25—H25124.0
C4—C5—H5119.7C27—C26—N3110.7 (5)
C5—C6—C7120.3 (5)C27—C26—H26124.7
C5—C6—H6119.8N3—C26—H26124.7
C7—C6—H6119.8C26—C27—N4105.4 (6)
C6—C7—C8121.1 (5)C26—C27—H27127.3
C6—C7—C12119.0 (5)N4—C27—H27127.3
C8—C7—C12119.9 (5)N1—C28—N2112.0 (5)
C9—C8—C7120.5 (6)N1—C28—H28124.0
C9—C8—H8119.8N2—C28—H28124.0
C7—C8—H8119.8N1—C29—C30110.4 (5)
C8—C9—C10119.9 (6)N1—C29—H29124.8
C8—C9—H9120.1C30—C29—H29124.8
C10—C9—H9120.1N2—C30—C29105.4 (5)
C11—C10—C9120.7 (6)N2—C30—H30127.3
C11—C10—H10119.7C29—C30—H30127.3
C9—C10—H10119.7N3—Cd1—N1104.92 (16)
C10—C11—C12121.8 (6)N3—Cd1—O3113.55 (17)
C10—C11—H11119.1N1—Cd1—O386.72 (14)
C12—C11—H11119.1N3—Cd1—O185.25 (14)
C11—C12—C7117.2 (5)N1—Cd1—O1110.02 (16)
C11—C12—C3123.0 (5)O3—Cd1—O1151.34 (16)
C7—C12—C3119.8 (5)N3—Cd1—O2138.65 (14)
O3—C13—O4121.1 (5)N1—Cd1—O287.71 (17)
O3—C13—C14117.9 (5)O3—Cd1—O2106.24 (15)
O4—C13—C14121.0 (5)O1—Cd1—O253.62 (13)
C15—C14—C13117.6 (4)N3—Cd1—O4100.77 (15)
C15—C14—H14A107.9N1—Cd1—O4139.07 (13)
C13—C14—H14A107.9O3—Cd1—O453.65 (12)
C15—C14—H14B107.9O1—Cd1—O4103.32 (14)
C13—C14—H14B107.9O2—Cd1—O493.62 (16)
H14A—C14—H14B107.2C28—N1—C29104.2 (5)
C16—C15—C24118.3 (6)C28—N1—Cd1125.4 (4)
C16—C15—C14120.4 (7)C29—N1—Cd1130.3 (3)
C24—C15—C14121.3 (6)C28—N2—C30107.8 (5)
C15—C16—C17121.9 (8)C28—N2—H2126.1
C15—C16—H16119.1C30—N2—H2126.1
C17—C16—H16119.1C25—N3—C26104.5 (5)
C18—C17—C16120.7 (8)C25—N3—Cd1123.6 (4)
C18—C17—H17119.6C26—N3—Cd1131.7 (3)
C16—C17—H17119.6C25—N4—C27107.4 (5)
C17—C18—C19120.5 (8)C25—N4—H4A126.3
C17—C18—H18119.7C27—N4—H4A126.3
C19—C18—H18119.7C1—O1—Cd192.6 (3)
C20—C19—C18121.2 (7)C1—O2—Cd192.7 (3)
C20—C19—C24120.6 (7)C13—O3—Cd196.7 (3)
C18—C19—C24118.2 (8)C13—O4—Cd188.2 (3)
C21—C20—C19120.8 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O4i0.861.922.735 (6)159
N4—H4A···O2ii0.861.952.772 (6)159
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O4i0.861.922.735 (6)159
N4—H4A···O2ii0.861.952.772 (6)159
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−1, y, z.
Acknowledgements top

The authors acknowledge Guang Dong Ocean University for supporting this work.

references
References top

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc, Madison, Wisconsin, USA.

Duan, J.-G., Liu, J.-W. & Wu, S. (2007). Acta Cryst. E63, m692–m694.

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