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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1471.
Published online 2010 October 30. doi:  10.1107/S1600536810043163
PMCID: PMC3009368

Dichlorido{2-morpholino-N-[1-(2-pyri­dyl)ethyl­idene]ethanamine-κ3 N,N′,N′′}cadmium

Abstract

In the title compound, [CdCl2(C13H19N3O)], the CdII ion is five-coordinate, with the N,N′,N′′-tridentate Schiff base ligand 2-morpholino-N-[1-(2-pyrid­yl)ethyl­idene]ethanamine and two Cl atoms in a distorted square-pyramidal geometry. In the crystal structure, C—H(...)Cl hydrogen-bonding inter­actions connect the mol­ecules into a three-dimensional network.

Related literature

For the crystal structures of similar compounds, see: Ikmal Hisham et al. (2009 [triangle]); Cai (2009 [triangle]).

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Object name is e-66-m1471-scheme1.jpg

Experimental

Crystal data

  • [CdCl2(C13H19N3O)]
  • M r = 416.61
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1471-efi1.jpg
  • a = 9.6357 (12) Å
  • b = 13.9300 (18) Å
  • c = 12.2514 (17) Å
  • β = 106.776 (2)°
  • V = 1574.5 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.73 mm−1
  • T = 100 K
  • 0.23 × 0.10 × 0.04 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.692, T max = 0.934
  • 9407 measured reflections
  • 3437 independent reflections
  • 2646 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.117
  • S = 1.08
  • 3437 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.81 e Å−3
  • Δρmin = −1.16 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043163/pv2344sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043163/pv2344Isup2.hkl

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

Acknowledgments

The authors thank the University of Malaya for funding this study (UMRG grant RG024/09BIO).

supplementary crystallographic information

Comment

The title compound has been obtained via the complexation of cadmium(II) chloride by the N,N,N-tridentate ligand, 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine, which had itself been prepared from the condensation of 4-(2-aminoethyl)morpholine and 2-acetylpyridine. The geometry of the complex can be defined as distorted square-pyramidal (τ = 0.18) with one of the chloride ligands in the apical position. Like the similar structures reported in the literature [Ikmal Hisham et al., 2009; Cai, 2009], the morpholine ring in the present complex adopts a chair conformation. In the crystal structure, the molecules are linked together through C—H···Cl interactions into a three dimensional network.

Experimental

A mixture of 4-(2-aminoethyl)morpholine (0.65 g, 5 mmol) and 2-acetylpyridine (0.61 g, 5 mmol) in ethanol (50 ml) was refluxed for 2 h followed by addition of a solution of cadmium(II) chloride (0.92 g, 5 mmol) in a minimum amount of water. The resulting solution was refluxed for 30 min, then evaporated partially and set aside at room temperature. The crystals of the cadmium(II) complex were obtained after a week.

Refinement

The hydrogen atoms were placed at calculated positions (C—H 0.95 - 0.99 Å) and were treated as riding on their parent atoms with U(H) set to 1.2–1.5 Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot of the title compound at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[CdCl2(C13H19N3O)]F(000) = 832
Mr = 416.61Dx = 1.758 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2378 reflections
a = 9.6357 (12) Åθ = 2.3–27.3°
b = 13.9300 (18) ŵ = 1.73 mm1
c = 12.2514 (17) ÅT = 100 K
β = 106.776 (2)°Lath, colorless
V = 1574.5 (4) Å30.23 × 0.10 × 0.04 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer3437 independent reflections
Radiation source: fine-focus sealed tube2646 reflections with I > 2σ(I)
graphiteRint = 0.043
[var phi] and ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→12
Tmin = 0.692, Tmax = 0.934k = −10→17
9407 measured reflectionsl = −15→15

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0488P)2 + 6.1933P] where P = (Fo2 + 2Fc2)/3
3437 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = −1.16 e Å3

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
Cd10.77057 (4)0.09902 (3)0.33319 (3)0.01533 (13)
Cl10.52520 (14)0.14366 (10)0.21865 (11)0.0195 (3)
Cl20.96418 (15)0.21768 (10)0.36618 (11)0.0210 (3)
O10.8174 (4)0.0583 (3)−0.0120 (3)0.0235 (9)
N10.7320 (5)0.1178 (3)0.5165 (4)0.0180 (10)
N20.7579 (5)−0.0471 (3)0.4170 (4)0.0173 (10)
N30.8461 (5)−0.0170 (3)0.2128 (4)0.0177 (10)
C10.7366 (6)0.2002 (4)0.5727 (4)0.0194 (11)
H10.76490.25670.54130.023*
C20.7020 (6)0.2073 (4)0.6749 (4)0.0205 (12)
H20.70790.26720.71310.025*
C30.6588 (7)0.1252 (5)0.7199 (4)0.0261 (14)
H30.63210.12810.78860.031*
C40.6552 (6)0.0378 (4)0.6629 (5)0.0214 (12)
H40.6271−0.01950.69270.026*
C50.6932 (6)0.0363 (4)0.5621 (4)0.0153 (11)
C60.7049 (6)−0.0549 (4)0.4993 (4)0.0154 (11)
C70.6593 (6)−0.1485 (4)0.5389 (5)0.0225 (12)
H7A0.6077−0.18700.47260.034*
H7B0.5951−0.13620.58660.034*
H7C0.7452−0.18360.58340.034*
C80.7876 (6)−0.1294 (4)0.3538 (4)0.0200 (12)
H8A0.6972−0.15150.29780.024*
H8B0.8274−0.18300.40670.024*
C90.8969 (6)−0.0984 (4)0.2929 (5)0.0204 (12)
H9A0.9881−0.07950.35040.024*
H9B0.9188−0.15380.24990.024*
C100.7321 (6)−0.0497 (4)0.1112 (4)0.0210 (12)
H10A0.6446−0.06770.13340.025*
H10B0.7662−0.10740.07940.025*
C110.6935 (6)0.0277 (4)0.0212 (5)0.0209 (12)
H11A0.61870.0031−0.04650.025*
H11B0.65210.08340.05110.025*
C120.9219 (6)0.0938 (4)0.0846 (5)0.0228 (12)
H12A0.88060.14890.11580.027*
H12B1.00650.11740.06190.027*
C130.9722 (6)0.0184 (4)0.1767 (5)0.0234 (13)
H13A1.0175−0.03570.14730.028*
H13B1.04560.04640.24300.028*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.0202 (2)0.0147 (2)0.01291 (19)0.00042 (16)0.00765 (14)0.00102 (15)
Cl10.0196 (6)0.0200 (7)0.0194 (6)0.0030 (5)0.0065 (5)0.0031 (5)
Cl20.0217 (7)0.0215 (7)0.0208 (6)−0.0038 (5)0.0076 (5)0.0009 (5)
O10.028 (2)0.029 (2)0.0161 (18)−0.0047 (19)0.0109 (17)−0.0021 (17)
N10.020 (2)0.023 (3)0.011 (2)0.0020 (19)0.0050 (18)0.0010 (18)
N20.023 (2)0.015 (2)0.014 (2)0.0009 (19)0.0050 (18)0.0000 (18)
N30.018 (2)0.023 (3)0.013 (2)0.0012 (19)0.0057 (18)−0.0006 (18)
C10.025 (3)0.017 (3)0.016 (2)−0.004 (2)0.005 (2)0.001 (2)
C20.026 (3)0.016 (3)0.018 (3)0.006 (2)0.004 (2)−0.004 (2)
C30.029 (3)0.039 (4)0.010 (2)0.007 (3)0.006 (2)0.002 (2)
C40.025 (3)0.025 (3)0.017 (3)0.000 (2)0.011 (2)0.003 (2)
C50.015 (3)0.017 (3)0.013 (2)0.001 (2)0.003 (2)0.004 (2)
C60.013 (2)0.018 (3)0.015 (2)0.002 (2)0.003 (2)0.003 (2)
C70.025 (3)0.021 (3)0.021 (3)−0.002 (2)0.007 (2)0.005 (2)
C80.032 (3)0.010 (3)0.019 (3)0.006 (2)0.008 (2)0.001 (2)
C90.029 (3)0.012 (3)0.021 (3)0.009 (2)0.009 (2)0.001 (2)
C100.026 (3)0.022 (3)0.015 (2)0.000 (2)0.006 (2)−0.004 (2)
C110.024 (3)0.024 (3)0.017 (3)−0.003 (2)0.008 (2)−0.001 (2)
C120.026 (3)0.024 (3)0.023 (3)−0.012 (3)0.014 (2)−0.008 (2)
C130.022 (3)0.031 (4)0.021 (3)0.002 (3)0.012 (2)−0.006 (2)

Geometric parameters (Å, °)

Cd1—N22.298 (5)C4—H40.9500
Cd1—N12.394 (4)C5—C61.506 (8)
Cd1—N32.437 (4)C6—C71.501 (8)
Cd1—Cl22.4374 (14)C7—H7A0.9800
Cd1—Cl12.4557 (14)C7—H7B0.9800
O1—C121.404 (7)C7—H7C0.9800
O1—C111.432 (6)C8—C91.519 (8)
N1—C11.332 (7)C8—H8A0.9900
N1—C51.364 (7)C8—H8B0.9900
N2—C61.261 (7)C9—H9A0.9900
N2—C81.458 (7)C9—H9B0.9900
N3—C101.474 (7)C10—C111.510 (8)
N3—C91.487 (7)C10—H10A0.9900
N3—C131.492 (7)C10—H10B0.9900
C1—C21.390 (7)C11—H11A0.9900
C1—H10.9500C11—H11B0.9900
C2—C31.385 (8)C12—C131.515 (8)
C2—H20.9500C12—H12A0.9900
C3—C41.398 (8)C12—H12B0.9900
C3—H30.9500C13—H13A0.9900
C4—C51.385 (7)C13—H13B0.9900
N2—Cd1—N168.60 (16)C6—C7—H7B109.5
N2—Cd1—N375.33 (15)H7A—C7—H7B109.5
N1—Cd1—N3142.63 (15)C6—C7—H7C109.5
N2—Cd1—Cl2131.54 (12)H7A—C7—H7C109.5
N1—Cd1—Cl295.10 (12)H7B—C7—H7C109.5
N3—Cd1—Cl2101.67 (11)N2—C8—C9107.9 (5)
N2—Cd1—Cl1108.24 (12)N2—C8—H8A110.1
N1—Cd1—Cl197.11 (11)C9—C8—H8A110.1
N3—Cd1—Cl1103.21 (11)N2—C8—H8B110.1
Cl2—Cd1—Cl1119.18 (5)C9—C8—H8B110.1
C12—O1—C11108.6 (4)H8A—C8—H8B108.4
C1—N1—C5118.5 (4)N3—C9—C8113.5 (4)
C1—N1—Cd1126.0 (4)N3—C9—H9A108.9
C5—N1—Cd1115.4 (3)C8—C9—H9A108.9
C6—N2—C8123.0 (5)N3—C9—H9B108.9
C6—N2—Cd1121.3 (4)C8—C9—H9B108.9
C8—N2—Cd1114.6 (3)H9A—C9—H9B107.7
C10—N3—C9110.2 (4)N3—C10—C11111.2 (5)
C10—N3—C13108.9 (4)N3—C10—H10A109.4
C9—N3—C13107.8 (4)C11—C10—H10A109.4
C10—N3—Cd1115.9 (3)N3—C10—H10B109.4
C9—N3—Cd1101.9 (3)C11—C10—H10B109.4
C13—N3—Cd1111.8 (3)H10A—C10—H10B108.0
N1—C1—C2123.1 (5)O1—C11—C10111.7 (5)
N1—C1—H1118.4O1—C11—H11A109.3
C2—C1—H1118.4C10—C11—H11A109.3
C3—C2—C1118.6 (5)O1—C11—H11B109.3
C3—C2—H2120.7C10—C11—H11B109.3
C1—C2—H2120.7H11A—C11—H11B107.9
C2—C3—C4119.1 (5)O1—C12—C13112.4 (5)
C2—C3—H3120.5O1—C12—H12A109.1
C4—C3—H3120.5C13—C12—H12A109.1
C5—C4—C3118.9 (5)O1—C12—H12B109.1
C5—C4—H4120.5C13—C12—H12B109.1
C3—C4—H4120.5H12A—C12—H12B107.9
N1—C5—C4121.8 (5)N3—C13—C12109.7 (5)
N1—C5—C6115.0 (4)N3—C13—H13A109.7
C4—C5—C6123.1 (5)C12—C13—H13A109.7
N2—C6—C7123.9 (5)N3—C13—H13B109.7
N2—C6—C5116.3 (5)C12—C13—H13B109.7
C7—C6—C5119.8 (4)H13A—C13—H13B108.2
C6—C7—H7A109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···Cl1i0.952.693.603 (6)161
C7—H7C···Cl2ii0.982.733.607 (6)149
C8—H8A···Cl2iii0.992.823.730 (6)153
C11—H11B···Cl10.992.803.654 (6)144

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+3/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2344).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cai, B.-H. (2009). Acta Cryst. E65, m142. [PMC free article] [PubMed]
  • Ikmal Hisham, N. A., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, m870. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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