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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m653.
Published online 2008 April 10. doi:  10.1107/S1600536808009409
PMCID: PMC2961099

Bis(1H-imidazole-κN 3)bis­(1-naph­tha­lene­acetato-κ2 O,O′)cadmium(II)

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0m653-scheme1.jpg

Experimental

Crystal data

  • [Cd(C12H9O2)2(C3H4N2)2]
  • M r = 618.95
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m653-efi1.jpg
  • a = 8.5275 (3) Å
  • b = 17.1596 (7) Å
  • c = 19.1198 (6) Å
  • β = 100.735 (2)°
  • V = 2748.81 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.84 mm−1
  • T = 296 (2) K
  • 0.26 × 0.23 × 0.21 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.812, T max = 0.844
  • 26061 measured reflections
  • 5399 independent reflections
  • 3336 reflections with I > 2σ(I)
  • R int = 0.089

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.142
  • S = 0.99
  • 5399 reflections
  • 340 parameters
  • H-atom parameters constrained
  • Δρmax = 0.57 e Å−3
  • Δρmin = −1.16 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009409/ng2436sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009409/ng2436Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
The structure of (I), showing the atomic numbering scheme. Non-H atoms are shown as 30% probability displacement ellipsoids.
Fig. 2.
The packing of structure (I).

Crystal data

[Cd(C12H9O2)2(C3H4N2)2]F000 = 1256
Mr = 618.95Dx = 1.496 Mg m3
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 mm1
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

Bruker APEXII area-detector diffractometer5399 independent reflections
Radiation source: fine-focus sealed tube3336 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.089
T = 296(2) Kθmax = 26.0º
[var phi] 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

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 Å3
340 parametersΔρmin = −1.16 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
C10.3023 (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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2436).

References

  • 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.
  • Liu, J.-W., Wang, W.-Y. & Gu, C.-S. (2006). Acta Cryst. E62, m3445–m3447.
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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