Dichlorido{N,N-dimethyl-N'-[1-(pyridin-2-yl)ethyl-idene]ethane-1,2-diamine-κN,N',N''}cadmium.

In the title compound, [CdCl(2)(C(11)H(17)N(3))], the Schiff base acts as an N,N',N''-tridentate ligand towards the Cd(II) ion. Two Cl atoms complete a distorted square-pyramidal geometry around the metal atom. In the crystal, a C-H⋯Cl inter-action connects pairs of mol-ecules into centrosymetric dimers.

Related literature

For the structure of a CuCl2 complex of the same Schiff base, see: Saleh Salga et al. (2010 ▶). For the structure of a similar CdII complex, see: Bian et al. (2003 ▶). For a description of the geometry of complexes with five-coordinate metal atoms, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[CdCl2(C11H17N3)]

M = 374.58

Triclinic,

a = 8.0276 (2) Å

b = 9.6048 (2) Å

c = 10.0851 (2) Å

α = 102.534 (1)°

β = 103.365 (1)°

γ = 97.850 (1)°

V = 724.09 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.86 mm−1

T = 100 K

0.23 × 0.11 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.674, T max = 0.929

5023 measured reflections

2652 independent reflections

2547 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.016

wR(F 2) = 0.038

S = 1.08

2652 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.39 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/S1600536811005538/pv2387sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005538/pv2387Isup2.hkl

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

[CdCl2(C11H17N3)]	Z = 2
Mr = 374.58	F(000) = 372
Triclinic, P1	Dx = 1.718 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0276 (2) Å	Cell parameters from 5105 reflections
b = 9.6048 (2) Å	θ = 2.2–29.7°
c = 10.0851 (2) Å	µ = 1.86 mm−1
α = 102.534 (1)°	T = 100 K
β = 103.365 (1)°	Plate, colorless
γ = 97.850 (1)°	0.23 × 0.11 × 0.04 mm
V = 724.09 (3) Å3

Bruker APEXII CCD diffractometer	2652 independent reflections
Radiation source: fine-focus sealed tube	2547 reflections with I > 2σ(I)
graphite	Rint = 0.014
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.674, Tmax = 0.929	k = −11→11
5023 measured reflections	l = −12→12

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)] = 0.016	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.038	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0151P)2 + 0.4207P] where P = (Fo2 + 2Fc2)/3
2652 reflections	(Δ/σ)max = 0.001
157 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.39 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	−0.076971 (16)	0.190459 (13)	0.205336 (13)	0.01438 (5)
Cl1	−0.19397 (6)	0.14396 (5)	−0.04976 (5)	0.02368 (11)
Cl2	−0.21885 (7)	0.34705 (5)	0.35214 (5)	0.02337 (11)
N1	−0.1880 (2)	−0.04027 (16)	0.23109 (16)	0.0155 (3)
N2	0.1417 (2)	0.10346 (17)	0.33828 (16)	0.0171 (3)
N3	0.1925 (2)	0.34724 (17)	0.22918 (16)	0.0187 (3)
C1	−0.3543 (3)	−0.1088 (2)	0.1769 (2)	0.0193 (4)
H1	−0.4351	−0.0611	0.1283	0.023*
C2	−0.4143 (3)	−0.2472 (2)	0.1886 (2)	0.0214 (4)
H2	−0.5330	−0.2941	0.1471	0.026*
C3	−0.2973 (3)	−0.3147 (2)	0.2619 (2)	0.0233 (4)
H3	−0.3346	−0.4091	0.2719	0.028*
C4	−0.1247 (3)	−0.2432 (2)	0.3208 (2)	0.0202 (4)
H4	−0.0429	−0.2874	0.3732	0.024*
C5	−0.0729 (2)	−0.1063 (2)	0.30211 (19)	0.0166 (4)
C6	0.1124 (2)	−0.0244 (2)	0.35613 (19)	0.0173 (4)
C7	0.2517 (3)	−0.0968 (2)	0.4217 (2)	0.0244 (4)
H7A	0.2968	−0.1510	0.3482	0.037*
H7B	0.2025	−0.1639	0.4697	0.037*
H7C	0.3470	−0.0229	0.4902	0.037*
C8	0.3182 (2)	0.1896 (2)	0.3762 (2)	0.0212 (4)
H8A	0.3840	0.1458	0.3117	0.025*
H8B	0.3803	0.1910	0.4737	0.025*
C9	0.3074 (3)	0.3439 (2)	0.3656 (2)	0.0211 (4)
H9A	0.2626	0.3932	0.4431	0.025*
H9B	0.4260	0.3985	0.3773	0.025*
C10	0.2668 (3)	0.2957 (2)	0.1115 (2)	0.0246 (4)
H10A	0.3822	0.3559	0.1282	0.037*
H10B	0.1898	0.3027	0.0233	0.037*
H10C	0.2779	0.1942	0.1045	0.037*
C11	0.1656 (3)	0.4971 (2)	0.2359 (2)	0.0286 (5)
H11A	0.2779	0.5613	0.2511	0.043*
H11B	0.1150	0.5301	0.3140	0.043*
H11C	0.0860	0.4995	0.1470	0.043*

	U11	U22	U33	U12	U13	U23
Cd1	0.01536 (8)	0.01317 (8)	0.01511 (8)	0.00330 (5)	0.00430 (5)	0.00417 (5)
Cl1	0.0233 (2)	0.0301 (3)	0.0159 (2)	0.0048 (2)	0.00258 (18)	0.00570 (19)
Cl2	0.0298 (3)	0.0205 (2)	0.0265 (2)	0.0112 (2)	0.0154 (2)	0.00792 (19)
N1	0.0182 (8)	0.0151 (7)	0.0148 (7)	0.0045 (6)	0.0055 (6)	0.0048 (6)
N2	0.0165 (8)	0.0180 (8)	0.0158 (8)	0.0040 (6)	0.0032 (6)	0.0031 (6)
N3	0.0202 (8)	0.0168 (8)	0.0194 (8)	0.0030 (6)	0.0076 (7)	0.0029 (6)
C1	0.0193 (10)	0.0203 (10)	0.0203 (9)	0.0059 (8)	0.0072 (8)	0.0063 (8)
C2	0.0200 (10)	0.0221 (10)	0.0230 (10)	0.0011 (8)	0.0091 (8)	0.0063 (8)
C3	0.0294 (11)	0.0165 (9)	0.0289 (11)	0.0041 (8)	0.0149 (9)	0.0084 (8)
C4	0.0264 (10)	0.0196 (10)	0.0211 (10)	0.0107 (8)	0.0114 (8)	0.0095 (8)
C5	0.0220 (10)	0.0162 (9)	0.0141 (9)	0.0075 (8)	0.0081 (7)	0.0033 (7)
C6	0.0205 (10)	0.0200 (9)	0.0129 (9)	0.0080 (8)	0.0056 (7)	0.0036 (7)
C7	0.0222 (10)	0.0253 (10)	0.0275 (11)	0.0083 (8)	0.0044 (9)	0.0107 (9)
C8	0.0169 (10)	0.0226 (10)	0.0218 (10)	0.0035 (8)	0.0028 (8)	0.0038 (8)
C9	0.0206 (10)	0.0194 (10)	0.0198 (10)	−0.0004 (8)	0.0057 (8)	−0.0001 (8)
C10	0.0239 (11)	0.0297 (11)	0.0202 (10)	0.0027 (9)	0.0100 (8)	0.0032 (8)
C11	0.0326 (12)	0.0171 (10)	0.0388 (12)	0.0030 (9)	0.0150 (10)	0.0083 (9)

Cd1—N2	2.3188 (15)	C4—C5	1.390 (3)
Cd1—N1	2.3644 (15)	C4—H4	0.9500
Cd1—N3	2.3909 (16)	C5—C6	1.499 (3)
Cd1—Cl1	2.4434 (5)	C6—C7	1.497 (3)
Cd1—Cl2	2.4561 (5)	C7—H7A	0.9800
N1—C1	1.335 (2)	C7—H7B	0.9800
N1—C5	1.350 (2)	C7—H7C	0.9800
N2—C6	1.277 (2)	C8—C9	1.522 (3)
N2—C8	1.459 (2)	C8—H8A	0.9900
N3—C10	1.471 (2)	C8—H8B	0.9900
N3—C11	1.474 (2)	C9—H9A	0.9900
N3—C9	1.478 (2)	C9—H9B	0.9900
C1—C2	1.389 (3)	C10—H10A	0.9800
C1—H1	0.9500	C10—H10B	0.9800
C2—C3	1.379 (3)	C10—H10C	0.9800
C2—H2	0.9500	C11—H11A	0.9800
C3—C4	1.388 (3)	C11—H11B	0.9800
C3—H3	0.9500	C11—H11C	0.9800
N2—Cd1—N1	69.42 (5)	N1—C5—C6	115.96 (16)
N2—Cd1—N3	73.39 (5)	C4—C5—C6	122.77 (17)
N1—Cd1—N3	141.34 (5)	N2—C6—C7	123.96 (18)
N2—Cd1—Cl1	131.13 (4)	N2—C6—C5	116.71 (16)
N1—Cd1—Cl1	98.62 (4)	C7—C6—C5	119.29 (16)
N3—Cd1—Cl1	97.82 (4)	C6—C7—H7A	109.5
N2—Cd1—Cl2	112.49 (4)	C6—C7—H7B	109.5
N1—Cd1—Cl2	100.86 (4)	H7A—C7—H7B	109.5
N3—Cd1—Cl2	102.71 (4)	C6—C7—H7C	109.5
Cl1—Cd1—Cl2	116.315 (17)	H7A—C7—H7C	109.5
C1—N1—C5	119.09 (16)	H7B—C7—H7C	109.5
C1—N1—Cd1	124.01 (12)	N2—C8—C9	109.01 (16)
C5—N1—Cd1	116.87 (12)	N2—C8—H8A	109.9
C6—N2—C8	121.86 (16)	C9—C8—H8A	109.9
C6—N2—Cd1	120.70 (13)	N2—C8—H8B	109.9
C8—N2—Cd1	116.44 (11)	C9—C8—H8B	109.9
C10—N3—C11	110.06 (16)	H8A—C8—H8B	108.3
C10—N3—C9	111.56 (15)	N3—C9—C8	112.34 (15)
C11—N3—C9	108.99 (15)	N3—C9—H9A	109.1
C10—N3—Cd1	110.95 (11)	C8—C9—H9A	109.1
C11—N3—Cd1	110.21 (12)	N3—C9—H9B	109.1
C9—N3—Cd1	104.94 (11)	C8—C9—H9B	109.1
N1—C1—C2	122.72 (18)	H9A—C9—H9B	107.9
N1—C1—H1	118.6	N3—C10—H10A	109.5
C2—C1—H1	118.6	N3—C10—H10B	109.5
C3—C2—C1	118.40 (18)	H10A—C10—H10B	109.5
C3—C2—H2	120.8	N3—C10—H10C	109.5
C1—C2—H2	120.8	H10A—C10—H10C	109.5
C2—C3—C4	119.34 (18)	H10B—C10—H10C	109.5
C2—C3—H3	120.3	N3—C11—H11A	109.5
C4—C3—H3	120.3	N3—C11—H11B	109.5
C3—C4—C5	119.17 (18)	H11A—C11—H11B	109.5
C3—C4—H4	120.4	N3—C11—H11C	109.5
C5—C4—H4	120.4	H11A—C11—H11C	109.5
N1—C5—C4	121.26 (17)	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···Cl2i	0.98	2.77	3.679 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯Cl2i	0.98	2.77	3.679 (2)	155

Symmetry code: (i) .