supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, m1518    [ doi:10.1107/S1600536808035915 ]

Dichlorido[3-dimethylamino-N-(2-pyridylmethylene)propylamine-[kappa]3N,N',N'']cadmium(II)

H. Lin, X.-H. Geng and Y.-L. Feng

Abstract top

In the title mononuclear Cd(II) complex, [CdCl2(C11H17N3)], the Cd(II) atom is coordinated by two Cl atoms and three N atoms from the tridentate Schiff base ligand in a distorted square-pyramidal environment. The three N atoms and one Cl atom constitute the base of the pyramid, whereas the other Cl atom occupies the apical position.

Comment top

Transition metal complexes with multidentate Schiff base ligands have been extensively studied recently for their various crystallographic features, enzymatic reactions, catalysis, electrochemical and magnetic properties (Mukherjee et al., 2004; Saha et al., 2003). Literatures (Dalai et al., 2002; Mukherjee et al., 2001a,b) revealed that Schiff base ligands derived from pyridine-2-carboxaldehyde and diamine usually act tridentate (NNN) ones. The molecule of the title complex (I) (Fig.1) comprises one cadmium(II) ion, one neutral N-(pyridin-2-yl-methylene)-3-dimethylaminopropylamine ligand and two Cl- ions. The Cd(II) atom is coordinated by two chlorine atoms and three nitrogen atoms from the tridentate ligand in a distorted square pyramidal environment. Four coordinated atoms of N(1), N(2), N(3) and Cl(1) constitute the base of the pyramid, whereas Cl(2) atom occupies the apical position.

Related literature top

For the properties of transition metal complexes with multidentate Schiff base ligands, see: Mukherjee et al. (2004); Saha et al. (2003). For Schiff base ligands derived from pyridine-2-carboxaldehyde and diamine acting as tridentate (NNN) ligands, see: Dalai et al. (2002); Mukherjee et al. (2001a,b). For the synthesis, see: Choudhury et al. (2001).

Experimental top

The tridentate Schiff base, N-(pyridin-2-yl-methylene)-3-dimethylaminopropylamine (C11H17N3), were prepared by reflux of 0.5 mmol of 3-dimethylaminopropylamine and 0.5 mmol of pyridine-2-carboxaldehyde in 10 ml of ethanol for 30 min, according to the literature method (Choudhury, et al., 2001). To 20 ml ethanolic and chloroformic solution (1:1) of the Schiff base (0.5 mmol), CdCl2.2.5H2O (0.5 mmol) in 5 ml water was added, with refluxing for 30 min. This mixture was cooled to room temperature and left to stand undisturbed. After 5 days colourless crystals (I) suitable for X-ray analysis were obtained.

Refinement top

The methyl groups were allowed to rotate to fit the electron density [C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C)]; the other H atoms were positioned geometrically [aromatic C—Haromatic 0.93 Å and aliphatic C—H = 0.97 Å, Uiso(H) = 1.2Ueq(C)].

Computing details top

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Dichlorido[3-dimethylamino-N-(2-pyridylmethylene)propylamine- κ3N,N',N'']cadmium(II) top
Crystal data top
[Cd(C11H17N3)Cl2]Z = 2
Mr = 374.59F(000) = 372
Triclinic, P1Dx = 1.732 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6407 (15) ÅCell parameters from 3284 reflections
b = 9.0312 (18) Åθ = 1.8–27.5°
c = 11.860 (2) ŵ = 1.88 mm−1
α = 97.81 (3)°T = 293 K
β = 103.95 (3)°Block, colourless
γ = 111.11 (3)°0.27 × 0.20 × 0.16 mm
V = 718.2 (3) Å3
Data collection top
Bruker APEX-II area-detector
diffractometer		3251 independent reflections
Radiation source: fine-focus sealed tube3149 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.632, Tmax = 0.754k = −11→11
12281 measured reflectionsl = −15→15
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)] = 0.018Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.050H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0281P)2 + 0.1317P]
where P = (Fo2 + 2Fc2)/3
3251 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.72 e Å−3
Crystal data top
[Cd(C11H17N3)Cl2]γ = 111.11 (3)°
Mr = 374.59V = 718.2 (3) Å3
Triclinic, P1Z = 2
a = 7.6407 (15) ÅMo Kα radiation
b = 9.0312 (18) ŵ = 1.88 mm−1
c = 11.860 (2) ÅT = 293 K
α = 97.81 (3)°0.27 × 0.20 × 0.16 mm
β = 103.95 (3)°
Data collection top
Bruker APEX-II area-detector
diffractometer		3251 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3149 reflections with I > 2σ(I)
Tmin = 0.632, Tmax = 0.754Rint = 0.020
12281 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.018H-atom parameters constrained
wR(F2) = 0.050Δρmax = 0.33 e Å−3
S = 1.14Δρmin = −0.72 e Å−3
3251 reflectionsAbsolute structure: ?
154 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Cd10.203590 (15)0.391482 (13)0.743794 (9)0.03482 (5)
Cl2−0.08758 (6)0.21422 (6)0.57078 (4)0.04931 (11)
Cl10.15476 (8)0.61916 (7)0.85160 (5)0.05592 (12)
N20.4378 (2)0.28768 (18)0.72437 (13)0.0403 (3)
N30.1569 (2)0.2335 (2)0.88963 (13)0.0475 (4)
N10.4442 (2)0.57453 (17)0.67777 (13)0.0367 (3)
C10.5909 (2)0.5312 (2)0.66530 (14)0.0374 (3)
C20.7401 (3)0.6249 (3)0.62553 (16)0.0472 (4)
H2A0.84080.59290.61890.057*
C30.7372 (3)0.7664 (2)0.59584 (17)0.0511 (5)
H3A0.83550.83100.56840.061*
C40.5876 (3)0.8108 (2)0.60728 (17)0.0508 (4)
H4A0.58290.90570.58730.061*
C50.4430 (3)0.7125 (2)0.64904 (17)0.0450 (4)
H5A0.34220.74350.65730.054*
C60.5781 (3)0.3739 (2)0.69156 (15)0.0422 (4)
H6A0.67500.33740.68380.051*
C70.4187 (3)0.1243 (2)0.7381 (2)0.0545 (5)
H7A0.53900.11230.73570.065*
H7B0.31090.04260.67120.065*
C80.3807 (4)0.0927 (3)0.8542 (2)0.0617 (6)
H8A0.3940−0.00780.86480.074*
H8B0.48170.18110.92020.074*
C90.1804 (4)0.0784 (3)0.8609 (2)0.0611 (5)
H9A0.08250.01250.78450.073*
H9B0.15050.01920.92110.073*
C10−0.0528 (3)0.1931 (3)0.8813 (2)0.0671 (6)
H10A−0.08740.12890.93710.101*
H10B−0.13600.13170.80140.101*
H10C−0.07070.29240.90000.101*
C110.2795 (4)0.3281 (3)1.01250 (18)0.0676 (6)
H11A0.25520.25921.06690.101*
H11B0.24710.41921.03340.101*
H11C0.41650.36761.01740.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.03228 (8)0.03880 (8)0.03500 (8)0.01555 (5)0.01208 (5)0.00852 (5)
Cl20.0374 (2)0.0603 (3)0.0398 (2)0.01477 (19)0.00686 (17)0.00374 (19)
Cl10.0643 (3)0.0572 (3)0.0562 (3)0.0338 (2)0.0266 (2)0.0059 (2)
N20.0416 (7)0.0423 (7)0.0395 (7)0.0232 (6)0.0094 (6)0.0068 (6)
N30.0484 (8)0.0496 (8)0.0342 (7)0.0104 (7)0.0097 (6)0.0114 (6)
N10.0354 (7)0.0394 (7)0.0366 (7)0.0163 (6)0.0137 (5)0.0070 (6)
C10.0317 (7)0.0468 (9)0.0297 (7)0.0156 (7)0.0076 (6)0.0024 (6)
C20.0326 (8)0.0654 (12)0.0386 (9)0.0165 (8)0.0120 (7)0.0057 (8)
C30.0444 (9)0.0539 (11)0.0396 (9)0.0032 (8)0.0164 (8)0.0050 (8)
C40.0613 (11)0.0404 (9)0.0455 (10)0.0133 (8)0.0205 (9)0.0087 (7)
C50.0500 (10)0.0421 (9)0.0476 (9)0.0212 (8)0.0205 (8)0.0101 (7)
C60.0379 (8)0.0535 (10)0.0401 (8)0.0269 (8)0.0111 (7)0.0062 (7)
C70.0593 (12)0.0429 (10)0.0631 (12)0.0289 (9)0.0131 (10)0.0075 (9)
C80.0744 (14)0.0457 (10)0.0634 (13)0.0297 (10)0.0078 (11)0.0193 (9)
C90.0699 (14)0.0435 (10)0.0601 (12)0.0121 (10)0.0175 (11)0.0188 (9)
C100.0568 (12)0.0839 (16)0.0576 (12)0.0151 (11)0.0277 (10)0.0289 (12)
C110.0787 (16)0.0705 (14)0.0348 (10)0.0200 (12)0.0046 (10)0.0076 (9)
Geometric parameters (Å, °) top
Cd1—N22.3418 (15)C4—C51.390 (3)
Cd1—N12.3627 (16)C4—H4A0.9300
Cd1—N32.3992 (16)C5—H5A0.9300
Cd1—Cl22.4624 (15)C6—H6A0.9300
Cd1—Cl12.4637 (8)C7—C81.517 (3)
N2—C61.260 (2)C7—H7A0.9700
N2—C71.465 (2)C7—H7B0.9700
N3—C111.469 (3)C8—C91.512 (3)
N3—C91.480 (3)C8—H8A0.9700
N3—C101.484 (3)C8—H8B0.9700
N1—C51.338 (2)C9—H9A0.9700
N1—C11.346 (2)C9—H9B0.9700
C1—C21.382 (2)C10—H10A0.9600
C1—C61.470 (3)C10—H10B0.9600
C2—C31.378 (3)C10—H10C0.9600
C2—H2A0.9300C11—H11A0.9600
C3—C41.370 (3)C11—H11B0.9600
C3—H3A0.9300C11—H11C0.9600
N2—Cd1—N170.27 (5)N1—C5—H5A119.0
N2—Cd1—N384.79 (6)C4—C5—H5A119.0
N1—Cd1—N3144.00 (6)N2—C6—C1120.98 (15)
N2—Cd1—Cl2102.80 (4)N2—C6—H6A119.5
N1—Cd1—Cl2109.74 (5)C1—C6—H6A119.5
N3—Cd1—Cl2100.64 (5)N2—C7—C8112.77 (17)
N2—Cd1—Cl1144.32 (5)N2—C7—H7A109.0
N1—Cd1—Cl191.30 (4)C8—C7—H7A109.0
N3—Cd1—Cl194.73 (5)N2—C7—H7B109.0
Cl2—Cd1—Cl1112.28 (3)C8—C7—H7B109.0
C6—N2—C7119.48 (16)H7A—C7—H7B107.8
C6—N2—Cd1117.01 (12)C9—C8—C7114.81 (19)
C7—N2—Cd1123.28 (12)C9—C8—H8A108.6
C11—N3—C9110.90 (18)C7—C8—H8A108.6
C11—N3—C10107.96 (18)C9—C8—H8B108.6
C9—N3—C10108.30 (18)C7—C8—H8B108.6
C11—N3—Cd1112.97 (13)H8A—C8—H8B107.5
C9—N3—Cd1113.53 (12)N3—C9—C8116.67 (17)
C10—N3—Cd1102.61 (13)N3—C9—H9A108.1
C5—N1—C1118.26 (15)C8—C9—H9A108.1
C5—N1—Cd1125.78 (12)N3—C9—H9B108.1
C1—N1—Cd1115.93 (11)C8—C9—H9B108.1
N1—C1—C2122.39 (17)H9A—C9—H9B107.3
N1—C1—C6115.78 (15)N3—C10—H10A109.5
C2—C1—C6121.77 (16)N3—C10—H10B109.5
C3—C2—C1118.88 (18)H10A—C10—H10B109.5
C3—C2—H2A120.6N3—C10—H10C109.5
C1—C2—H2A120.6H10A—C10—H10C109.5
C4—C3—C2119.15 (17)H10B—C10—H10C109.5
C4—C3—H3A120.4N3—C11—H11A109.5
C2—C3—H3A120.4N3—C11—H11B109.5
C3—C4—C5119.26 (19)H11A—C11—H11B109.5
C3—C4—H4A120.4N3—C11—H11C109.5
C5—C4—H4A120.4H11A—C11—H11C109.5
N1—C5—C4122.05 (18)H11B—C11—H11C109.5
N1—Cd1—N2—C61.15 (12)N3—Cd1—N1—C147.48 (16)
N3—Cd1—N2—C6−152.45 (14)Cl2—Cd1—N1—C1−98.36 (11)
Cl2—Cd1—N2—C6107.80 (13)Cl1—Cd1—N1—C1147.36 (11)
Cl1—Cd1—N2—C6−61.59 (16)C5—N1—C1—C20.8 (2)
N1—Cd1—N2—C7−173.34 (15)Cd1—N1—C1—C2178.90 (13)
N3—Cd1—N2—C733.06 (14)C5—N1—C1—C6−176.60 (15)
Cl2—Cd1—N2—C7−66.69 (14)Cd1—N1—C1—C61.52 (18)
Cl1—Cd1—N2—C7123.92 (13)N1—C1—C2—C3−1.0 (3)
N2—Cd1—N3—C1193.26 (16)C6—C1—C2—C3176.24 (16)
N1—Cd1—N3—C1147.9 (2)C1—C2—C3—C40.4 (3)
Cl2—Cd1—N3—C11−164.66 (15)C2—C3—C4—C50.3 (3)
Cl1—Cd1—N3—C11−50.92 (16)C1—N1—C5—C40.0 (3)
N2—Cd1—N3—C9−34.13 (14)Cd1—N1—C5—C4−177.95 (14)
N1—Cd1—N3—C9−79.53 (16)C3—C4—C5—N1−0.5 (3)
Cl2—Cd1—N3—C967.95 (14)C7—N2—C6—C1173.88 (16)
Cl1—Cd1—N3—C9−178.31 (13)Cd1—N2—C6—C1−0.8 (2)
N2—Cd1—N3—C10−150.77 (14)N1—C1—C6—N2−0.5 (2)
N1—Cd1—N3—C10163.83 (13)C2—C1—C6—N2−177.89 (17)
Cl2—Cd1—N3—C10−48.69 (14)C6—N2—C7—C8133.5 (2)
Cl1—Cd1—N3—C1065.05 (14)Cd1—N2—C7—C8−52.1 (2)
N2—Cd1—N1—C5176.55 (16)N2—C7—C8—C968.8 (2)
N3—Cd1—N1—C5−134.56 (15)C11—N3—C9—C8−66.7 (2)
Cl2—Cd1—N1—C579.59 (15)C10—N3—C9—C8175.00 (18)
Cl1—Cd1—N1—C5−34.69 (14)Cd1—N3—C9—C861.7 (2)
N2—Cd1—N1—C1−1.40 (11)C7—C8—C9—N3−79.3 (2)
references
References top

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

Choudhury, C. R., Dey, S. K., Mondal, N., Mitra, S., Mahalli, S. O. G. & Malik, K. M. A. (2001). J. Chem. Crystallogr. 31, 57–62.

Dalai, S., Mukherjee, S. K., Drew, M. B. G., Lu, T.-H. & Chaudhuri, N. R. (2002). Inorg. Chim. Acta, 335, 85–90.

Mukherjee, S. K., Dalai, S., Mostafa, G., Lu, T.-H., Rentschler, E. & Chaudhuri, N. R. (2001a). New J. Chem. 25, 1203–1207.

Mukherjee, S. K., Dalai, S., Zangrando, E., Lloret, F. & Chaudhuri, N. R. (2001b). Chem. Commun. pp. 1444–1445.

Mukherjee, S. K., El Fallah, M. S., Vicente, R., Escuer, A., Solans, X., Font-Bardia, M., Matsushita, T., Gramlich, V. & Mitra, S. (2004). Inorg. Chem. 43, 2427–2434.

Saha, M. K., Dey, D. K., Samanta, B., Edwards, A. J., Clegg, W. & Mitra, S. (2003). J. Chem. Soc. Dalton Trans. pp. 488–492.

Sheldrick, G. M. (1996). SADABS. University of Göettingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.