Dichlorido{2-morpholino-N-[1-(2-pyri-dyl)ethyl-idene]ethanamine-κN,N',N''}cadmium.

In the title compound, [CdCl(2)(C(13)H(19)N(3)O)], the Cd(II) ion is five-coordinate, with the N,N',N''-tridentate Schiff base ligand 2-morpholino-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine and two Cl atoms in a distorted square-pyramidal geometry. In the crystal structure, C-H⋯Cl hydrogen-bonding inter-actions connect the mol-ecules into a three-dimensional network.

Related literature

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

Experimental

Crystal data

[CdCl2(C13H19N3O)]

M = 416.61

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 and publCIF (Westrip, 2010 ▶).

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

[CdCl2(C13H19N3O)]	F(000) = 832
Mr = 416.61	Dx = 1.758 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2378 reflections
a = 9.6357 (12) Å	θ = 2.3–27.3°
b = 13.9300 (18) Å	µ = 1.73 mm−1
c = 12.2514 (17) Å	T = 100 K
β = 106.776 (2)°	Lath, colorless
V = 1574.5 (4) Å3	0.23 × 0.10 × 0.04 mm
Z = 4

Bruker APEXII CCD diffractometer	3437 independent reflections
Radiation source: fine-focus sealed tube	2646 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→12
Tmin = 0.692, Tmax = 0.934	k = −10→17
9407 measured reflections	l = −15→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-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 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −1.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cd1	0.77057 (4)	0.09902 (3)	0.33319 (3)	0.01533 (13)
Cl1	0.52520 (14)	0.14366 (10)	0.21865 (11)	0.0195 (3)
Cl2	0.96418 (15)	0.21768 (10)	0.36618 (11)	0.0210 (3)
O1	0.8174 (4)	0.0583 (3)	−0.0120 (3)	0.0235 (9)
N1	0.7320 (5)	0.1178 (3)	0.5165 (4)	0.0180 (10)
N2	0.7579 (5)	−0.0471 (3)	0.4170 (4)	0.0173 (10)
N3	0.8461 (5)	−0.0170 (3)	0.2128 (4)	0.0177 (10)
C1	0.7366 (6)	0.2002 (4)	0.5727 (4)	0.0194 (11)
H1	0.7649	0.2567	0.5413	0.023*
C2	0.7020 (6)	0.2073 (4)	0.6749 (4)	0.0205 (12)
H2	0.7079	0.2672	0.7131	0.025*
C3	0.6588 (7)	0.1252 (5)	0.7199 (4)	0.0261 (14)
H3	0.6321	0.1281	0.7886	0.031*
C4	0.6552 (6)	0.0378 (4)	0.6629 (5)	0.0214 (12)
H4	0.6271	−0.0195	0.6927	0.026*
C5	0.6932 (6)	0.0363 (4)	0.5621 (4)	0.0153 (11)
C6	0.7049 (6)	−0.0549 (4)	0.4993 (4)	0.0154 (11)
C7	0.6593 (6)	−0.1485 (4)	0.5389 (5)	0.0225 (12)
H7A	0.6077	−0.1870	0.4726	0.034*
H7B	0.5951	−0.1362	0.5866	0.034*
H7C	0.7452	−0.1836	0.5834	0.034*
C8	0.7876 (6)	−0.1294 (4)	0.3538 (4)	0.0200 (12)
H8A	0.6972	−0.1515	0.2978	0.024*
H8B	0.8274	−0.1830	0.4067	0.024*
C9	0.8969 (6)	−0.0984 (4)	0.2929 (5)	0.0204 (12)
H9A	0.9881	−0.0795	0.3504	0.024*
H9B	0.9188	−0.1538	0.2499	0.024*
C10	0.7321 (6)	−0.0497 (4)	0.1112 (4)	0.0210 (12)
H10A	0.6446	−0.0677	0.1334	0.025*
H10B	0.7662	−0.1074	0.0794	0.025*
C11	0.6935 (6)	0.0277 (4)	0.0212 (5)	0.0209 (12)
H11A	0.6187	0.0031	−0.0465	0.025*
H11B	0.6521	0.0834	0.0511	0.025*
C12	0.9219 (6)	0.0938 (4)	0.0846 (5)	0.0228 (12)
H12A	0.8806	0.1489	0.1158	0.027*
H12B	1.0065	0.1174	0.0619	0.027*
C13	0.9722 (6)	0.0184 (4)	0.1767 (5)	0.0234 (13)
H13A	1.0175	−0.0357	0.1473	0.028*
H13B	1.0456	0.0464	0.2430	0.028*

	U11	U22	U33	U12	U13	U23
Cd1	0.0202 (2)	0.0147 (2)	0.01291 (19)	0.00042 (16)	0.00765 (14)	0.00102 (15)
Cl1	0.0196 (6)	0.0200 (7)	0.0194 (6)	0.0030 (5)	0.0065 (5)	0.0031 (5)
Cl2	0.0217 (7)	0.0215 (7)	0.0208 (6)	−0.0038 (5)	0.0076 (5)	0.0009 (5)
O1	0.028 (2)	0.029 (2)	0.0161 (18)	−0.0047 (19)	0.0109 (17)	−0.0021 (17)
N1	0.020 (2)	0.023 (3)	0.011 (2)	0.0020 (19)	0.0050 (18)	0.0010 (18)
N2	0.023 (2)	0.015 (2)	0.014 (2)	0.0009 (19)	0.0050 (18)	0.0000 (18)
N3	0.018 (2)	0.023 (3)	0.013 (2)	0.0012 (19)	0.0057 (18)	−0.0006 (18)
C1	0.025 (3)	0.017 (3)	0.016 (2)	−0.004 (2)	0.005 (2)	0.001 (2)
C2	0.026 (3)	0.016 (3)	0.018 (3)	0.006 (2)	0.004 (2)	−0.004 (2)
C3	0.029 (3)	0.039 (4)	0.010 (2)	0.007 (3)	0.006 (2)	0.002 (2)
C4	0.025 (3)	0.025 (3)	0.017 (3)	0.000 (2)	0.011 (2)	0.003 (2)
C5	0.015 (3)	0.017 (3)	0.013 (2)	0.001 (2)	0.003 (2)	0.004 (2)
C6	0.013 (2)	0.018 (3)	0.015 (2)	0.002 (2)	0.003 (2)	0.003 (2)
C7	0.025 (3)	0.021 (3)	0.021 (3)	−0.002 (2)	0.007 (2)	0.005 (2)
C8	0.032 (3)	0.010 (3)	0.019 (3)	0.006 (2)	0.008 (2)	0.001 (2)
C9	0.029 (3)	0.012 (3)	0.021 (3)	0.009 (2)	0.009 (2)	0.001 (2)
C10	0.026 (3)	0.022 (3)	0.015 (2)	0.000 (2)	0.006 (2)	−0.004 (2)
C11	0.024 (3)	0.024 (3)	0.017 (3)	−0.003 (2)	0.008 (2)	−0.001 (2)
C12	0.026 (3)	0.024 (3)	0.023 (3)	−0.012 (3)	0.014 (2)	−0.008 (2)
C13	0.022 (3)	0.031 (4)	0.021 (3)	0.002 (3)	0.012 (2)	−0.006 (2)

Cd1—N2	2.298 (5)	C4—H4	0.9500
Cd1—N1	2.394 (4)	C5—C6	1.506 (8)
Cd1—N3	2.437 (4)	C6—C7	1.501 (8)
Cd1—Cl2	2.4374 (14)	C7—H7A	0.9800
Cd1—Cl1	2.4557 (14)	C7—H7B	0.9800
O1—C12	1.404 (7)	C7—H7C	0.9800
O1—C11	1.432 (6)	C8—C9	1.519 (8)
N1—C1	1.332 (7)	C8—H8A	0.9900
N1—C5	1.364 (7)	C8—H8B	0.9900
N2—C6	1.261 (7)	C9—H9A	0.9900
N2—C8	1.458 (7)	C9—H9B	0.9900
N3—C10	1.474 (7)	C10—C11	1.510 (8)
N3—C9	1.487 (7)	C10—H10A	0.9900
N3—C13	1.492 (7)	C10—H10B	0.9900
C1—C2	1.390 (7)	C11—H11A	0.9900
C1—H1	0.9500	C11—H11B	0.9900
C2—C3	1.385 (8)	C12—C13	1.515 (8)
C2—H2	0.9500	C12—H12A	0.9900
C3—C4	1.398 (8)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.385 (7)	C13—H13B	0.9900
N2—Cd1—N1	68.60 (16)	C6—C7—H7B	109.5
N2—Cd1—N3	75.33 (15)	H7A—C7—H7B	109.5
N1—Cd1—N3	142.63 (15)	C6—C7—H7C	109.5
N2—Cd1—Cl2	131.54 (12)	H7A—C7—H7C	109.5
N1—Cd1—Cl2	95.10 (12)	H7B—C7—H7C	109.5
N3—Cd1—Cl2	101.67 (11)	N2—C8—C9	107.9 (5)
N2—Cd1—Cl1	108.24 (12)	N2—C8—H8A	110.1
N1—Cd1—Cl1	97.11 (11)	C9—C8—H8A	110.1
N3—Cd1—Cl1	103.21 (11)	N2—C8—H8B	110.1
Cl2—Cd1—Cl1	119.18 (5)	C9—C8—H8B	110.1
C12—O1—C11	108.6 (4)	H8A—C8—H8B	108.4
C1—N1—C5	118.5 (4)	N3—C9—C8	113.5 (4)
C1—N1—Cd1	126.0 (4)	N3—C9—H9A	108.9
C5—N1—Cd1	115.4 (3)	C8—C9—H9A	108.9
C6—N2—C8	123.0 (5)	N3—C9—H9B	108.9
C6—N2—Cd1	121.3 (4)	C8—C9—H9B	108.9
C8—N2—Cd1	114.6 (3)	H9A—C9—H9B	107.7
C10—N3—C9	110.2 (4)	N3—C10—C11	111.2 (5)
C10—N3—C13	108.9 (4)	N3—C10—H10A	109.4
C9—N3—C13	107.8 (4)	C11—C10—H10A	109.4
C10—N3—Cd1	115.9 (3)	N3—C10—H10B	109.4
C9—N3—Cd1	101.9 (3)	C11—C10—H10B	109.4
C13—N3—Cd1	111.8 (3)	H10A—C10—H10B	108.0
N1—C1—C2	123.1 (5)	O1—C11—C10	111.7 (5)
N1—C1—H1	118.4	O1—C11—H11A	109.3
C2—C1—H1	118.4	C10—C11—H11A	109.3
C3—C2—C1	118.6 (5)	O1—C11—H11B	109.3
C3—C2—H2	120.7	C10—C11—H11B	109.3
C1—C2—H2	120.7	H11A—C11—H11B	107.9
C2—C3—C4	119.1 (5)	O1—C12—C13	112.4 (5)
C2—C3—H3	120.5	O1—C12—H12A	109.1
C4—C3—H3	120.5	C13—C12—H12A	109.1
C5—C4—C3	118.9 (5)	O1—C12—H12B	109.1
C5—C4—H4	120.5	C13—C12—H12B	109.1
C3—C4—H4	120.5	H12A—C12—H12B	107.9
N1—C5—C4	121.8 (5)	N3—C13—C12	109.7 (5)
N1—C5—C6	115.0 (4)	N3—C13—H13A	109.7
C4—C5—C6	123.1 (5)	C12—C13—H13A	109.7
N2—C6—C7	123.9 (5)	N3—C13—H13B	109.7
N2—C6—C5	116.3 (5)	C12—C13—H13B	109.7
C7—C6—C5	119.8 (4)	H13A—C13—H13B	108.2
C6—C7—H7A	109.5

D—H···A	D—H	H···A	D···A	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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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) ; (ii) ; (iii) .