Dichlorido[3-dimethyl­amino-N-(2-pyridylmethyl­ene)propyl­amine-κ3N,N′,N′′]cadmium(II)

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

doi:10.1107/S1600536808035915

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1518

doi:10.1107/S1600536808035915

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Dichlorido[3-dimethylamino-N-(2-pyridylmethylene)propylamine-κ³N,N′,N′′]cadmium(II)

Hong Lin,^a ^* Xiao-Hong Geng ^b and Yun-Long Feng ^b

^aJinhua Professional Technical College, Jinhua, Zhejiang 321007, People's Republic of China, and ^bZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: jh_ll@126.com

(Received 13 October 2008; accepted 1 November 2008; online 8 November 2008)

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.

Related literature

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

Crystal data

[CdCl₂(C₁₁H₁₇N₃)]
M_r = 374.59
Triclinic, $[P \overline 1]$
a = 7.6407 (15) Å
b = 9.0312 (18) Å
c = 11.860 (2) Å
α = 97.81 (3)°
β = 103.95 (3)°
γ = 111.11 (3)°
V = 718.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 293 (2) K
0.27 × 0.20 × 0.16 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.631, T_max = 0.753
12281 measured reflections
3251 independent reflections
3149 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.050
S = 1.14
3251 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808035915/at2652sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035915/at2652Isup2.hkl

checkCIF report

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.

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

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
M_r = 374.59	F(000) = 372
Triclinic, P1	D_x = 1.732 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6407 (15) Å	Cell parameters from 3284 reflections
b = 9.0312 (18) Å	θ = 1.8–27.5°
c = 11.860 (2) Å	µ = 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 tube	3149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.632, T_max = 0.754	k = −11→11
12281 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.050	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0281P)² + 0.1317P] where P = (F_o² + 2F_c²)/3
3251 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Cd(C₁₁H₁₇N₃)Cl₂]	γ = 111.11 (3)°
M_r = 374.59	V = 718.2 (3) Å³
Triclinic, P1	Z = 2
a = 7.6407 (15) Å	Mo Kα radiation
b = 9.0312 (18) Å	µ = 1.88 mm⁻¹
c = 11.860 (2) Å	T = 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)
T_min = 0.632, T_max = 0.754	R_int = 0.020
12281 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.050	H-atom parameters constrained
S = 1.14	Δρ_max = 0.33 e Å⁻³
3251 reflections	Δρ_min = −0.72 e Å⁻³
154 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

	x	y	z	U_iso*/U_eq
Cd1	0.203590 (15)	0.391482 (13)	0.743794 (9)	0.03482 (5)
Cl2	−0.08758 (6)	0.21422 (6)	0.57078 (4)	0.04931 (11)
Cl1	0.15476 (8)	0.61916 (7)	0.85160 (5)	0.05592 (12)
N2	0.4378 (2)	0.28768 (18)	0.72437 (13)	0.0403 (3)
N3	0.1569 (2)	0.2335 (2)	0.88963 (13)	0.0475 (4)
N1	0.4442 (2)	0.57453 (17)	0.67777 (13)	0.0367 (3)
C1	0.5909 (2)	0.5312 (2)	0.66530 (14)	0.0374 (3)
C2	0.7401 (3)	0.6249 (3)	0.62553 (16)	0.0472 (4)
H2A	0.8408	0.5929	0.6189	0.057*
C3	0.7372 (3)	0.7664 (2)	0.59584 (17)	0.0511 (5)
H3A	0.8355	0.8310	0.5684	0.061*
C4	0.5876 (3)	0.8108 (2)	0.60728 (17)	0.0508 (4)
H4A	0.5829	0.9057	0.5873	0.061*
C5	0.4430 (3)	0.7125 (2)	0.64904 (17)	0.0450 (4)
H5A	0.3422	0.7435	0.6573	0.054*
C6	0.5781 (3)	0.3739 (2)	0.69156 (15)	0.0422 (4)
H6A	0.6750	0.3374	0.6838	0.051*
C7	0.4187 (3)	0.1243 (2)	0.7381 (2)	0.0545 (5)
H7A	0.5390	0.1123	0.7357	0.065*
H7B	0.3109	0.0426	0.6712	0.065*
C8	0.3807 (4)	0.0927 (3)	0.8542 (2)	0.0617 (6)
H8A	0.3940	−0.0078	0.8648	0.074*
H8B	0.4817	0.1811	0.9202	0.074*
C9	0.1804 (4)	0.0784 (3)	0.8609 (2)	0.0611 (5)
H9A	0.0825	0.0125	0.7845	0.073*
H9B	0.1505	0.0192	0.9211	0.073*
C10	−0.0528 (3)	0.1931 (3)	0.8813 (2)	0.0671 (6)
H10A	−0.0874	0.1289	0.9371	0.101*
H10B	−0.1360	0.1317	0.8014	0.101*
H10C	−0.0707	0.2924	0.9000	0.101*
C11	0.2795 (4)	0.3281 (3)	1.01250 (18)	0.0676 (6)
H11A	0.2552	0.2592	1.0669	0.101*
H11B	0.2471	0.4192	1.0334	0.101*
H11C	0.4165	0.3676	1.0174	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.03228 (8)	0.03880 (8)	0.03500 (8)	0.01555 (5)	0.01208 (5)	0.00852 (5)
Cl2	0.0374 (2)	0.0603 (3)	0.0398 (2)	0.01477 (19)	0.00686 (17)	0.00374 (19)
Cl1	0.0643 (3)	0.0572 (3)	0.0562 (3)	0.0338 (2)	0.0266 (2)	0.0059 (2)
N2	0.0416 (7)	0.0423 (7)	0.0395 (7)	0.0232 (6)	0.0094 (6)	0.0068 (6)
N3	0.0484 (8)	0.0496 (8)	0.0342 (7)	0.0104 (7)	0.0097 (6)	0.0114 (6)
N1	0.0354 (7)	0.0394 (7)	0.0366 (7)	0.0163 (6)	0.0137 (5)	0.0070 (6)
C1	0.0317 (7)	0.0468 (9)	0.0297 (7)	0.0156 (7)	0.0076 (6)	0.0024 (6)
C2	0.0326 (8)	0.0654 (12)	0.0386 (9)	0.0165 (8)	0.0120 (7)	0.0057 (8)
C3	0.0444 (9)	0.0539 (11)	0.0396 (9)	0.0032 (8)	0.0164 (8)	0.0050 (8)
C4	0.0613 (11)	0.0404 (9)	0.0455 (10)	0.0133 (8)	0.0205 (9)	0.0087 (7)
C5	0.0500 (10)	0.0421 (9)	0.0476 (9)	0.0212 (8)	0.0205 (8)	0.0101 (7)
C6	0.0379 (8)	0.0535 (10)	0.0401 (8)	0.0269 (8)	0.0111 (7)	0.0062 (7)
C7	0.0593 (12)	0.0429 (10)	0.0631 (12)	0.0289 (9)	0.0131 (10)	0.0075 (9)
C8	0.0744 (14)	0.0457 (10)	0.0634 (13)	0.0297 (10)	0.0078 (11)	0.0193 (9)
C9	0.0699 (14)	0.0435 (10)	0.0601 (12)	0.0121 (10)	0.0175 (11)	0.0188 (9)
C10	0.0568 (12)	0.0839 (16)	0.0576 (12)	0.0151 (11)	0.0277 (10)	0.0289 (12)
C11	0.0787 (16)	0.0705 (14)	0.0348 (10)	0.0200 (12)	0.0046 (10)	0.0076 (9)

Geometric parameters (Å, º) top

Cd1—N2	2.3418 (15)	C4—C5	1.390 (3)
Cd1—N1	2.3627 (16)	C4—H4A	0.9300
Cd1—N3	2.3992 (16)	C5—H5A	0.9300
Cd1—Cl2	2.4624 (15)	C6—H6A	0.9300
Cd1—Cl1	2.4637 (8)	C7—C8	1.517 (3)
N2—C6	1.260 (2)	C7—H7A	0.9700
N2—C7	1.465 (2)	C7—H7B	0.9700
N3—C11	1.469 (3)	C8—C9	1.512 (3)
N3—C9	1.480 (3)	C8—H8A	0.9700
N3—C10	1.484 (3)	C8—H8B	0.9700
N1—C5	1.338 (2)	C9—H9A	0.9700
N1—C1	1.346 (2)	C9—H9B	0.9700
C1—C2	1.382 (2)	C10—H10A	0.9600
C1—C6	1.470 (3)	C10—H10B	0.9600
C2—C3	1.378 (3)	C10—H10C	0.9600
C2—H2A	0.9300	C11—H11A	0.9600
C3—C4	1.370 (3)	C11—H11B	0.9600
C3—H3A	0.9300	C11—H11C	0.9600

N2—Cd1—N1	70.27 (5)	N1—C5—H5A	119.0
N2—Cd1—N3	84.79 (6)	C4—C5—H5A	119.0
N1—Cd1—N3	144.00 (6)	N2—C6—C1	120.98 (15)
N2—Cd1—Cl2	102.80 (4)	N2—C6—H6A	119.5
N1—Cd1—Cl2	109.74 (5)	C1—C6—H6A	119.5
N3—Cd1—Cl2	100.64 (5)	N2—C7—C8	112.77 (17)
N2—Cd1—Cl1	144.32 (5)	N2—C7—H7A	109.0
N1—Cd1—Cl1	91.30 (4)	C8—C7—H7A	109.0
N3—Cd1—Cl1	94.73 (5)	N2—C7—H7B	109.0
Cl2—Cd1—Cl1	112.28 (3)	C8—C7—H7B	109.0
C6—N2—C7	119.48 (16)	H7A—C7—H7B	107.8
C6—N2—Cd1	117.01 (12)	C9—C8—C7	114.81 (19)
C7—N2—Cd1	123.28 (12)	C9—C8—H8A	108.6
C11—N3—C9	110.90 (18)	C7—C8—H8A	108.6
C11—N3—C10	107.96 (18)	C9—C8—H8B	108.6
C9—N3—C10	108.30 (18)	C7—C8—H8B	108.6
C11—N3—Cd1	112.97 (13)	H8A—C8—H8B	107.5
C9—N3—Cd1	113.53 (12)	N3—C9—C8	116.67 (17)
C10—N3—Cd1	102.61 (13)	N3—C9—H9A	108.1
C5—N1—C1	118.26 (15)	C8—C9—H9A	108.1
C5—N1—Cd1	125.78 (12)	N3—C9—H9B	108.1
C1—N1—Cd1	115.93 (11)	C8—C9—H9B	108.1
N1—C1—C2	122.39 (17)	H9A—C9—H9B	107.3
N1—C1—C6	115.78 (15)	N3—C10—H10A	109.5
C2—C1—C6	121.77 (16)	N3—C10—H10B	109.5
C3—C2—C1	118.88 (18)	H10A—C10—H10B	109.5
C3—C2—H2A	120.6	N3—C10—H10C	109.5
C1—C2—H2A	120.6	H10A—C10—H10C	109.5
C4—C3—C2	119.15 (17)	H10B—C10—H10C	109.5
C4—C3—H3A	120.4	N3—C11—H11A	109.5
C2—C3—H3A	120.4	N3—C11—H11B	109.5
C3—C4—C5	119.26 (19)	H11A—C11—H11B	109.5
C3—C4—H4A	120.4	N3—C11—H11C	109.5
C5—C4—H4A	120.4	H11A—C11—H11C	109.5
N1—C5—C4	122.05 (18)	H11B—C11—H11C	109.5

N1—Cd1—N2—C6	1.15 (12)	N3—Cd1—N1—C1	47.48 (16)
N3—Cd1—N2—C6	−152.45 (14)	Cl2—Cd1—N1—C1	−98.36 (11)
Cl2—Cd1—N2—C6	107.80 (13)	Cl1—Cd1—N1—C1	147.36 (11)
Cl1—Cd1—N2—C6	−61.59 (16)	C5—N1—C1—C2	0.8 (2)
N1—Cd1—N2—C7	−173.34 (15)	Cd1—N1—C1—C2	178.90 (13)
N3—Cd1—N2—C7	33.06 (14)	C5—N1—C1—C6	−176.60 (15)
Cl2—Cd1—N2—C7	−66.69 (14)	Cd1—N1—C1—C6	1.52 (18)
Cl1—Cd1—N2—C7	123.92 (13)	N1—C1—C2—C3	−1.0 (3)
N2—Cd1—N3—C11	93.26 (16)	C6—C1—C2—C3	176.24 (16)
N1—Cd1—N3—C11	47.9 (2)	C1—C2—C3—C4	0.4 (3)
Cl2—Cd1—N3—C11	−164.66 (15)	C2—C3—C4—C5	0.3 (3)
Cl1—Cd1—N3—C11	−50.92 (16)	C1—N1—C5—C4	0.0 (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—C9	67.95 (14)	C7—N2—C6—C1	173.88 (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—C10	163.83 (13)	C2—C1—C6—N2	−177.89 (17)
Cl2—Cd1—N3—C10	−48.69 (14)	C6—N2—C7—C8	133.5 (2)
Cl1—Cd1—N3—C10	65.05 (14)	Cd1—N2—C7—C8	−52.1 (2)
N2—Cd1—N1—C5	176.55 (16)	N2—C7—C8—C9	68.8 (2)
N3—Cd1—N1—C5	−134.56 (15)	C11—N3—C9—C8	−66.7 (2)
Cl2—Cd1—N1—C5	79.59 (15)	C10—N3—C9—C8	175.00 (18)
Cl1—Cd1—N1—C5	−34.69 (14)	Cd1—N3—C9—C8	61.7 (2)
N2—Cd1—N1—C1	−1.40 (11)	C7—C8—C9—N3	−79.3 (2)

Experimental details

Crystal data
Chemical formula	[Cd(C₁₁H₁₇N₃)Cl₂]
M_r	374.59
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.6407 (15), 9.0312 (18), 11.860 (2)
α, β, γ (°)	97.81 (3), 103.95 (3), 111.11 (3)
V (Å³)	718.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.27 × 0.20 × 0.16

Data collection
Diffractometer	Bruker APEX-II area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.632, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	12281, 3251, 3149
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.050, 1.14
No. of reflections	3251
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.72

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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