metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Di­chlorido{2-morpholino-N-[1-(2-pyri­dyl)ethyl­­idene]ethanamine-κ3N,N′,N′′}cadmium

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 21 October 2010; accepted 22 October 2010; online 30 October 2010)

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[Ikmal Hisham, N. A., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, m870.]); Cai (2009[Cai, B.-H. (2009). Acta Cryst. E65, m142.]).

[Scheme 1]

Experimental

Crystal data
  • [CdCl2(C13H19N3O)]

  • Mr = 416.61

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.692, Tmax = 0.934

  • 9407 measured reflections

  • 3437 independent reflections

  • 2646 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯Cl1i 0.95 2.69 3.603 (6) 161
C7—H7C⋯Cl2ii 0.98 2.73 3.607 (6) 149
C8—H8A⋯Cl2iii 0.99 2.82 3.730 (6) 153
C11—H11B⋯Cl1 0.99 2.80 3.654 (6) 144
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y, -z+1; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Structure description top

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.

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

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the title compound at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Dichlorido{2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine- κ3N,N',N''}cadmium(II) top
Crystal data top
[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 top
Bruker APEXII CCD
diffractometer
3437 independent reflections
Radiation source: fine-focus sealed tube2646 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 812
Tmin = 0.692, Tmax = 0.934k = 1017
9407 measured reflectionsl = 1515
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.08 w = 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
Crystal data top
[CdCl2(C13H19N3O)]V = 1574.5 (4) Å3
Mr = 416.61Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.6357 (12) ŵ = 1.73 mm1
b = 13.9300 (18) ÅT = 100 K
c = 12.2514 (17) Å0.23 × 0.10 × 0.04 mm
β = 106.776 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
3437 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2646 reflections with I > 2σ(I)
Tmin = 0.692, Tmax = 0.934Rint = 0.043
9407 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.08Δρmax = 0.81 e Å3
3437 reflectionsΔρmin = 1.16 e Å3
182 parameters
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
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)
H40.62710.01950.69270.026*
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)
H7A0.60770.18700.47260.034*
H7B0.59510.13620.58660.034*
H7C0.74520.18360.58340.034*
C80.7876 (6)0.1294 (4)0.3538 (4)0.0200 (12)
H8A0.69720.15150.29780.024*
H8B0.82740.18300.40670.024*
C90.8969 (6)0.0984 (4)0.2929 (5)0.0204 (12)
H9A0.98810.07950.35040.024*
H9B0.91880.15380.24990.024*
C100.7321 (6)0.0497 (4)0.1112 (4)0.0210 (12)
H10A0.64460.06770.13340.025*
H10B0.76620.10740.07940.025*
C110.6935 (6)0.0277 (4)0.0212 (5)0.0209 (12)
H11A0.61870.00310.04650.025*
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)
H13A1.01750.03570.14730.028*
H13B1.04560.04640.24300.028*
Atomic displacement parameters (Å2) top
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, º) top
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, º) top
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, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[CdCl2(C13H19N3O)]
Mr416.61
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)9.6357 (12), 13.9300 (18), 12.2514 (17)
β (°) 106.776 (2)
V3)1574.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.73
Crystal size (mm)0.23 × 0.10 × 0.04
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.692, 0.934
No. of measured, independent and
observed [I > 2σ(I)] reflections
9407, 3437, 2646
Rint0.043
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.117, 1.08
No. of reflections3437
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.81, 1.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···Cl1i0.952.693.603 (6)160.9
C7—H7C···Cl2ii0.982.733.607 (6)149.3
C8—H8A···Cl2iii0.992.823.730 (6)152.6
C11—H11B···Cl10.992.803.654 (6)144.4
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y, z+1; (iii) x+3/2, y1/2, z+1/2.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCai, B.-H. (2009). Acta Cryst. E65, m142.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationIkmal Hisham, N. A., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, m870.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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