Dichlorido{N-[(5-methyl-thio-phen-2-yl)methyl-idene]-2-(pyridin-2-yl)ethanamine-κ(2) N,N'}palladium(II).

In the title compound, [PdCl2(C13H14N2S)], the Pd(II) ion is coordinated by two N atoms of the chelating bidentate ligand and two chloride anions, giving rise to a distorted square-planar geometry. The methyl-substituted thio-phene arm and the pyridine ring are connected to the metal cation through N atoms to form a six-membered chelate ring with a boat conformation, making the complex stable.

Related literature

For the synthesis of imino-pyridyl ligands and their transition metal-based complexes, see: Onani & Motswainyana (2011 ▶); Motswainyana et al. (2011 ▶); Bianchini et al. (2010 ▶). For related structures, see: Motswainyana et al. (2012 ▶); Chen et al. (2007 ▶). For applications of these complexes, see: Ardizzoia et al. (2009 ▶); Tianpengfei et al. (2011 ▶).

Experimental

Crystal data

[PdCl2(C13H14N2S)]

M = 407.62

Monoclinic,

a = 12.0110 (5) Å

b = 9.1633 (4) Å

c = 13.6456 (6) Å

β = 97.930 (1)°

V = 1487.48 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.73 mm−1

T = 173 K

0.15 × 0.07 × 0.04 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.781, T max = 0.934

14701 measured reflections

3706 independent reflections

3129 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.056

S = 1.02

3706 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049240/bh2466sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049240/bh2466Isup2.hkl

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

[PdCl2(C13H14N2S)]	F(000) = 808
Mr = 407.62	Dx = 1.820 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14701 reflections
a = 12.0110 (5) Å	θ = 1.7–28.3°
b = 9.1633 (4) Å	µ = 1.73 mm−1
c = 13.6456 (6) Å	T = 173 K
β = 97.930 (1)°	Needle, yellow
V = 1487.48 (11) Å3	0.15 × 0.07 × 0.04 mm
Z = 4

Bruker Kappa DUO APEXII diffractometer	3706 independent reflections
Radiation source: fine-focus sealed tube	3129 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
0.5° φ scans and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −16→16
Tmin = 0.781, Tmax = 0.934	k = −12→12
14701 measured reflections	l = −18→18

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0227P)2 + 0.6596P] where P = (Fo2 + 2Fc2)/3
3706 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.62 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Pd1	0.253855 (14)	0.164855 (19)	0.101073 (12)	0.01838 (6)
Cl1	0.35052 (5)	0.08399 (7)	0.24845 (4)	0.02846 (14)
Cl2	0.08238 (5)	0.11869 (7)	0.15214 (4)	0.02567 (13)
S1	0.18709 (5)	0.48733 (6)	0.13240 (4)	0.02374 (13)
N1	0.39778 (16)	0.2026 (2)	0.04460 (14)	0.0229 (4)
N2	0.18590 (15)	0.2349 (2)	−0.03402 (14)	0.0200 (4)
C1	0.4789 (2)	0.2919 (3)	0.0894 (2)	0.0276 (5)
H1	0.4720	0.3299	0.1531	0.033*
C2	0.5710 (2)	0.3293 (3)	0.0452 (2)	0.0356 (6)
H2	0.6260	0.3947	0.0768	0.043*
C3	0.5820 (2)	0.2704 (4)	−0.0453 (2)	0.0397 (7)
H3	0.6455	0.2940	−0.0768	0.048*
C4	0.5005 (2)	0.1767 (3)	−0.0909 (2)	0.0346 (6)
H4	0.5085	0.1342	−0.1530	0.042*
C5	0.4071 (2)	0.1452 (3)	−0.04537 (18)	0.0248 (5)
C6	0.3119 (2)	0.0495 (3)	−0.08966 (18)	0.0295 (6)
H6A	0.3029	−0.0311	−0.0431	0.035*
H6B	0.3316	0.0057	−0.1513	0.035*
C7	0.1988 (2)	0.1301 (3)	−0.11346 (17)	0.0260 (5)
H7A	0.1962	0.1824	−0.1772	0.031*
H7B	0.1363	0.0588	−0.1196	0.031*
C8	0.15436 (18)	0.3656 (3)	−0.05905 (17)	0.0208 (5)
H8	0.1332	0.3829	−0.1277	0.025*
C9	0.14775 (18)	0.4873 (3)	0.00534 (16)	0.0203 (5)
C10	0.10937 (19)	0.6228 (3)	−0.02615 (18)	0.0240 (5)
H10	0.0836	0.6448	−0.0935	0.029*
C11	0.11169 (19)	0.7260 (3)	0.05032 (18)	0.0248 (5)
H11	0.0878	0.8244	0.0401	0.030*
C12	0.15202 (19)	0.6694 (3)	0.14103 (18)	0.0235 (5)
C13	0.1685 (2)	0.7445 (3)	0.23892 (19)	0.0337 (6)
H13A	0.1380	0.8436	0.2315	0.051*
H13B	0.2490	0.7490	0.2638	0.051*
H13C	0.1295	0.6900	0.2858	0.051*

	U11	U22	U33	U12	U13	U23
Pd1	0.02171 (9)	0.01803 (9)	0.01521 (9)	0.00063 (7)	0.00192 (6)	0.00031 (7)
Cl1	0.0322 (3)	0.0323 (3)	0.0194 (3)	0.0027 (2)	−0.0018 (2)	0.0039 (2)
Cl2	0.0246 (3)	0.0253 (3)	0.0277 (3)	0.0007 (2)	0.0059 (2)	0.0051 (2)
S1	0.0342 (3)	0.0184 (3)	0.0181 (3)	0.0019 (2)	0.0018 (2)	0.0024 (2)
N1	0.0241 (10)	0.0231 (10)	0.0212 (10)	0.0031 (8)	0.0020 (8)	0.0018 (8)
N2	0.0226 (9)	0.0210 (10)	0.0162 (9)	0.0002 (8)	0.0017 (7)	−0.0010 (8)
C1	0.0250 (12)	0.0270 (13)	0.0300 (14)	0.0025 (10)	0.0011 (10)	0.0013 (11)
C2	0.0246 (12)	0.0367 (16)	0.0445 (17)	0.0001 (11)	0.0011 (11)	0.0089 (13)
C3	0.0240 (13)	0.0556 (19)	0.0410 (17)	0.0075 (13)	0.0104 (12)	0.0203 (15)
C4	0.0353 (14)	0.0474 (17)	0.0226 (13)	0.0178 (13)	0.0094 (11)	0.0080 (12)
C5	0.0291 (12)	0.0252 (12)	0.0203 (12)	0.0087 (10)	0.0036 (9)	0.0031 (10)
C6	0.0392 (14)	0.0271 (13)	0.0220 (13)	0.0062 (11)	0.0034 (10)	−0.0071 (10)
C7	0.0345 (13)	0.0254 (13)	0.0171 (12)	−0.0009 (10)	−0.0005 (10)	−0.0060 (9)
C8	0.0203 (10)	0.0273 (13)	0.0150 (11)	−0.0006 (9)	0.0025 (8)	0.0022 (9)
C9	0.0204 (11)	0.0247 (12)	0.0163 (11)	0.0007 (9)	0.0039 (8)	0.0038 (9)
C10	0.0231 (11)	0.0264 (12)	0.0226 (12)	0.0010 (9)	0.0033 (9)	0.0077 (10)
C11	0.0232 (11)	0.0204 (12)	0.0318 (14)	0.0027 (9)	0.0073 (10)	0.0045 (10)
C12	0.0251 (11)	0.0186 (11)	0.0281 (13)	−0.0014 (9)	0.0083 (9)	0.0018 (10)
C13	0.0490 (16)	0.0222 (13)	0.0319 (15)	−0.0002 (12)	0.0123 (12)	−0.0023 (11)

Pd1—N2	2.0152 (18)	C5—C6	1.500 (3)
Pd1—N1	2.017 (2)	C6—C7	1.541 (3)
Pd1—Cl1	2.3016 (6)	C6—H6A	0.9900
Pd1—Cl2	2.3027 (6)	C6—H6B	0.9900
S1—C12	1.729 (2)	C7—H7A	0.9900
S1—C9	1.733 (2)	C7—H7B	0.9900
N1—C1	1.352 (3)	C8—C9	1.429 (3)
N1—C5	1.355 (3)	C8—H8	0.9500
N2—C8	1.288 (3)	C9—C10	1.373 (3)
N2—C7	1.472 (3)	C10—C11	1.406 (3)
C1—C2	1.374 (4)	C10—H10	0.9500
C1—H1	0.9500	C11—C12	1.368 (3)
C2—C3	1.371 (4)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.491 (3)
C3—C4	1.384 (4)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.385 (4)	C13—H13C	0.9800
C4—H4	0.9500
N2—Pd1—N1	81.73 (7)	C5—C6—H6B	108.8
N2—Pd1—Cl1	173.54 (6)	C7—C6—H6B	108.8
N1—Pd1—Cl1	91.91 (6)	H6A—C6—H6B	107.7
N2—Pd1—Cl2	93.96 (5)	N2—C7—C6	109.68 (19)
N1—Pd1—Cl2	175.20 (6)	N2—C7—H7A	109.7
Cl1—Pd1—Cl2	92.34 (2)	C6—C7—H7A	109.7
C12—S1—C9	91.90 (12)	N2—C7—H7B	109.7
C1—N1—C5	120.0 (2)	C6—C7—H7B	109.7
C1—N1—Pd1	122.21 (17)	H7A—C7—H7B	108.2
C5—N1—Pd1	117.53 (16)	N2—C8—C9	127.0 (2)
C8—N2—C7	117.9 (2)	N2—C8—H8	116.5
C8—N2—Pd1	127.30 (16)	C9—C8—H8	116.5
C7—N2—Pd1	113.28 (15)	C10—C9—C8	123.9 (2)
N1—C1—C2	121.7 (3)	C10—C9—S1	110.26 (18)
N1—C1—H1	119.1	C8—C9—S1	125.80 (17)
C2—C1—H1	119.1	C9—C10—C11	113.9 (2)
C3—C2—C1	118.7 (3)	C9—C10—H10	123.1
C3—C2—H2	120.6	C11—C10—H10	123.1
C1—C2—H2	120.6	C12—C11—C10	112.6 (2)
C2—C3—C4	119.9 (3)	C12—C11—H11	123.7
C2—C3—H3	120.0	C10—C11—H11	123.7
C4—C3—H3	120.0	C11—C12—C13	128.5 (2)
C3—C4—C5	119.6 (3)	C11—C12—S1	111.32 (18)
C3—C4—H4	120.2	C13—C12—S1	120.16 (18)
C5—C4—H4	120.2	C12—C13—H13A	109.5
N1—C5—C4	119.9 (2)	C12—C13—H13B	109.5
N1—C5—C6	116.0 (2)	H13A—C13—H13B	109.5
C4—C5—C6	124.1 (2)	C12—C13—H13C	109.5
C5—C6—C7	114.0 (2)	H13A—C13—H13C	109.5
C5—C6—H6A	108.8	H13B—C13—H13C	109.5
C7—C6—H6A	108.8
N2—Pd1—N1—C1	124.39 (19)	N1—C5—C6—C7	64.5 (3)
Cl1—Pd1—N1—C1	−56.80 (18)	C4—C5—C6—C7	−115.2 (3)
N2—Pd1—N1—C5	−49.93 (17)	C8—N2—C7—C6	132.5 (2)
Cl1—Pd1—N1—C5	128.88 (16)	Pd1—N2—C7—C6	−34.5 (2)
N1—Pd1—N2—C8	−94.6 (2)	C5—C6—C7—N2	−39.7 (3)
Cl2—Pd1—N2—C8	87.59 (19)	C7—N2—C8—C9	−173.1 (2)
N1—Pd1—N2—C7	71.03 (16)	Pd1—N2—C8—C9	−8.1 (3)
Cl2—Pd1—N2—C7	−106.83 (15)	N2—C8—C9—C10	−177.5 (2)
C5—N1—C1—C2	1.3 (4)	N2—C8—C9—S1	3.0 (4)
Pd1—N1—C1—C2	−172.90 (19)	C12—S1—C9—C10	−0.28 (18)
N1—C1—C2—C3	−2.0 (4)	C12—S1—C9—C8	179.2 (2)
C1—C2—C3—C4	0.7 (4)	C8—C9—C10—C11	−179.3 (2)
C2—C3—C4—C5	1.2 (4)	S1—C9—C10—C11	0.2 (3)
C1—N1—C5—C4	0.7 (3)	C9—C10—C11—C12	0.0 (3)
Pd1—N1—C5—C4	175.19 (18)	C10—C11—C12—C13	179.1 (2)
C1—N1—C5—C6	−179.0 (2)	C10—C11—C12—S1	−0.2 (3)
Pd1—N1—C5—C6	−4.5 (3)	C9—S1—C12—C11	0.27 (19)
C3—C4—C5—N1	−2.0 (4)	C9—S1—C12—C13	−179.1 (2)
C3—C4—C5—C6	177.7 (2)