Bis{2-[(2,4-dimethyl-phen-yl)imino-meth-yl]pyridine-κN,N'}bis-(thio-cyanato-κN)cadmium.

The title compound, [Cd(NCS)(2)(C(14)H(14)N(2))(2)], features crystallographic inversion symmetry with the Cd(II) ion located on a centre of inversion. The Cd(II) ion is six-coordinated in a slightly distorted octa-hedral geometry with the thiocyanate anions in axial positions. The angle between the benzene and pyridine rings is 69.64 (9)°. An inter-molecular C-H⋯S hydrogen bond stabilizes the crystal structure.

Related literature

For the medicinal and pharmaceutical application of Schiff base compounds, see: Azza & Abu (2006 ▶); Dudek & Dudek (1966 ▶); Pandeya et al. (1999 ▶); Panneerselvam et al. (2005 ▶); Singh et al. (2006 ▶); Sridhar et al. (2001 ▶); Mladenova et al. (2002 ▶); Walsh et al. (1996 ▶). For the crystal structures of imino­pyridine complexes, see: Talei Bavil Olyai et al. (2008 ▶); Talei Bavil Olyai, Gholami Troujeni et al. (2010 ▶); Talei Bavil Olyai, Razzaghi Fard et al. (2010 ▶); Fallah Nejad et al. (2010 ▶); Loni et al. (2011 ▶).

Experimental

Crystal data

[Cd(NCS)2(C14H14N2)2]

M = 649.13

Orthorhombic,

a = 11.285 (2) Å

b = 15.048 (3) Å

c = 17.576 (4) Å

V = 2984.7 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.90 mm−1

T = 298 K

0.45 × 0.4 × 0.4 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶)T min = 0.406, T max = 0.430

12952 measured reflections

4016 independent reflections

2589 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.075

S = 1.00

4016 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.39 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002772/bt5786sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002772/bt5786Isup2.hkl

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

[Cd(NCS)2(C14H14N2)2]	F(000) = 1320.0
Mr = 649.13	Dx = 1.445 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4016 reflections
a = 11.285 (2) Å	θ = 2.3–29.2°
b = 15.048 (3) Å	µ = 0.90 mm−1
c = 17.576 (4) Å	T = 298 K
V = 2984.7 (10) Å3	Block, yellow
Z = 4	0.45 × 0.4 × 0.4 mm

Stoe IPDS II diffractometer	4016 independent reflections
Radiation source: fine-focus sealed tube	2589 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 2.3°
rotation method scans	h = −15→13
Absorption correction: numerical shape of crystal determined optically	k = −20→18
Tmin = 0.406, Tmax = 0.430	l = −20→24
12952 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.0706P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4016 reflections	Δρmax = 0.20 e Å−3
181 parameters	Δρmin = −0.39 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (4)

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	0.5000	0.0000	0.5000	0.05113 (8)
S1	0.81414 (5)	0.10677 (4)	0.32032 (3)	0.08019 (19)
N1	0.40527 (12)	0.08917 (9)	0.40838 (7)	0.0506 (3)
N2	0.56541 (13)	0.09386 (10)	0.59987 (8)	0.0522 (3)
N3	0.66504 (15)	0.03255 (13)	0.42813 (10)	0.0687 (4)
C1	0.40926 (15)	0.18477 (11)	0.40648 (9)	0.0484 (4)
C2	0.34254 (16)	0.23310 (12)	0.45844 (9)	0.0537 (4)
C3	0.35215 (18)	0.32527 (12)	0.45528 (11)	0.0607 (5)
H3	0.3075	0.3589	0.4892	0.073*
C4	0.42425 (17)	0.36928 (12)	0.40456 (11)	0.0603 (5)
C5	0.49090 (17)	0.31881 (14)	0.35509 (12)	0.0645 (5)
H5	0.5413	0.3469	0.3208	0.077*
C6	0.48400 (16)	0.22711 (14)	0.35565 (11)	0.0585 (5)
H6	0.5295	0.1939	0.3219	0.070*
C7	0.2607 (2)	0.18931 (16)	0.51445 (12)	0.0771 (6)
H7A	0.2006	0.1569	0.4875	0.116*
H7B	0.2241	0.2338	0.5457	0.116*
H7C	0.3051	0.1492	0.5459	0.116*
C8	0.4294 (2)	0.46981 (15)	0.40349 (16)	0.0888 (7)
H8A	0.3775	0.4931	0.4419	0.133*
H8B	0.4049	0.4911	0.3545	0.133*
H8C	0.5090	0.4890	0.4134	0.133*
C9	0.37889 (16)	0.04762 (12)	0.34795 (10)	0.0560 (4)
H9	0.3556	0.0800	0.3054	0.067*
C10	0.61622 (16)	0.04953 (12)	0.65736 (9)	0.0530 (4)
C11	0.66386 (19)	0.09220 (14)	0.71998 (12)	0.0700 (5)
H11	0.6992	0.0597	0.7588	0.084*
C12	0.6583 (2)	0.18377 (15)	0.72401 (13)	0.0756 (6)
H12	0.6895	0.2139	0.7656	0.091*
C13	0.6062 (2)	0.22922 (14)	0.66575 (12)	0.0698 (5)
H13	0.6016	0.2909	0.6670	0.084*
C14	0.56032 (18)	0.18261 (13)	0.60500 (11)	0.0619 (5)
H14	0.5243	0.2142	0.5658	0.074*
C15	0.72622 (16)	0.06333 (12)	0.38293 (10)	0.0522 (4)

	U11	U22	U33	U12	U13	U23
Cd1	0.06666 (13)	0.05083 (12)	0.03589 (10)	−0.00527 (8)	−0.00409 (7)	0.00119 (7)
S1	0.0866 (4)	0.0912 (4)	0.0628 (3)	−0.0209 (3)	0.0033 (3)	0.0211 (3)
N1	0.0607 (8)	0.0512 (9)	0.0399 (7)	0.0054 (7)	0.0001 (6)	−0.0038 (6)
N2	0.0612 (9)	0.0500 (9)	0.0453 (8)	−0.0035 (7)	0.0000 (6)	−0.0037 (6)
N3	0.0716 (11)	0.0741 (11)	0.0603 (10)	−0.0121 (9)	0.0033 (8)	0.0023 (9)
C1	0.0585 (10)	0.0476 (10)	0.0390 (8)	0.0059 (7)	−0.0049 (7)	−0.0004 (7)
C2	0.0597 (10)	0.0555 (11)	0.0459 (9)	0.0052 (8)	0.0011 (8)	−0.0029 (8)
C3	0.0684 (11)	0.0553 (11)	0.0584 (10)	0.0112 (9)	−0.0002 (9)	−0.0086 (9)
C4	0.0667 (11)	0.0533 (11)	0.0609 (11)	−0.0013 (9)	−0.0121 (9)	0.0007 (9)
C5	0.0689 (12)	0.0657 (13)	0.0590 (11)	−0.0056 (10)	0.0020 (9)	0.0101 (10)
C6	0.0706 (12)	0.0607 (12)	0.0442 (9)	0.0069 (9)	0.0049 (8)	0.0000 (9)
C7	0.0892 (15)	0.0687 (13)	0.0733 (13)	0.0118 (12)	0.0293 (12)	0.0053 (11)
C8	0.1038 (19)	0.0544 (12)	0.108 (2)	−0.0100 (13)	−0.0139 (15)	0.0021 (13)
C9	0.0691 (11)	0.0571 (12)	0.0418 (9)	0.0060 (9)	−0.0044 (8)	−0.0015 (8)
C10	0.0618 (10)	0.0546 (12)	0.0426 (9)	0.0016 (8)	−0.0012 (8)	−0.0067 (8)
C11	0.0891 (14)	0.0677 (14)	0.0531 (10)	0.0060 (11)	−0.0140 (10)	−0.0143 (10)
C12	0.0940 (16)	0.0691 (15)	0.0636 (11)	−0.0024 (12)	−0.0115 (12)	−0.0225 (11)
C13	0.0852 (14)	0.0517 (11)	0.0727 (13)	−0.0019 (10)	0.0019 (11)	−0.0165 (10)
C14	0.0712 (13)	0.0538 (11)	0.0607 (11)	−0.0017 (9)	−0.0021 (10)	0.0008 (9)
C15	0.0588 (10)	0.0489 (9)	0.0491 (9)	−0.0032 (8)	−0.0094 (8)	0.0014 (8)

Cd1—N3i	2.3032 (17)	C5—C6	1.382 (3)
Cd1—N3	2.3032 (17)	C5—H5	0.9300
Cd1—N1	2.3529 (14)	C6—H6	0.9300
Cd1—N1i	2.3529 (14)	C7—H7A	0.9600
Cd1—N2i	2.3708 (14)	C7—H7B	0.9600
Cd1—N2	2.3708 (14)	C7—H7C	0.9600
S1—C15	1.619 (2)	C8—H8A	0.9600
N1—C9	1.268 (2)	C8—H8B	0.9600
N1—C1	1.440 (2)	C8—H8C	0.9600
N2—C10	1.340 (2)	C9—C10i	1.466 (3)
N2—C14	1.340 (2)	C9—H9	0.9300
N3—C15	1.150 (2)	C10—C11	1.383 (2)
C1—C6	1.384 (3)	C10—C9i	1.466 (3)
C1—C2	1.389 (2)	C11—C12	1.381 (3)
C2—C3	1.392 (2)	C11—H11	0.9300
C2—C7	1.502 (3)	C12—C13	1.365 (3)
C3—C4	1.377 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.378 (3)
C4—C5	1.378 (3)	C13—H13	0.9300
C4—C8	1.514 (3)	C14—H14	0.9300
N3i—Cd1—N3	180.0	C6—C5—H5	119.5
N3i—Cd1—N1	97.43 (6)	C5—C6—C1	119.89 (18)
N3—Cd1—N1	82.57 (6)	C5—C6—H6	120.1
N3i—Cd1—N1i	82.57 (6)	C1—C6—H6	120.1
N3—Cd1—N1i	97.43 (6)	C2—C7—H7A	109.5
N1—Cd1—N1i	180.00 (5)	C2—C7—H7B	109.5
N3i—Cd1—N2i	91.58 (6)	H7A—C7—H7B	109.5
N3—Cd1—N2i	88.42 (6)	C2—C7—H7C	109.5
N1—Cd1—N2i	72.03 (5)	H7A—C7—H7C	109.5
N1i—Cd1—N2i	107.97 (5)	H7B—C7—H7C	109.5
N3i—Cd1—N2	88.42 (6)	C4—C8—H8A	109.5
N3—Cd1—N2	91.58 (6)	C4—C8—H8B	109.5
N1—Cd1—N2	107.97 (5)	H8A—C8—H8B	109.5
N1i—Cd1—N2	72.03 (5)	C4—C8—H8C	109.5
N2i—Cd1—N2	180.0	H8A—C8—H8C	109.5
C9—N1—C1	118.73 (15)	H8B—C8—H8C	109.5
C9—N1—Cd1	113.50 (12)	N1—C9—C10i	122.43 (16)
C1—N1—Cd1	124.85 (10)	N1—C9—H9	118.8
C10—N2—C14	117.64 (16)	C10i—C9—H9	118.8
C10—N2—Cd1	113.27 (11)	N2—C10—C11	122.37 (17)
C14—N2—Cd1	129.08 (12)	N2—C10—C9i	117.69 (15)
C15—N3—Cd1	161.83 (17)	C11—C10—C9i	119.94 (17)
C6—C1—C2	120.91 (16)	C12—C11—C10	119.1 (2)
C6—C1—N1	119.60 (16)	C12—C11—H11	120.4
C2—C1—N1	119.40 (15)	C10—C11—H11	120.4
C1—C2—C3	116.94 (17)	C13—C12—C11	118.8 (2)
C1—C2—C7	122.30 (17)	C13—C12—H12	120.6
C3—C2—C7	120.73 (17)	C11—C12—H12	120.6
C4—C3—C2	123.43 (18)	C12—C13—C14	119.2 (2)
C4—C3—H3	118.3	C12—C13—H13	120.4
C2—C3—H3	118.3	C14—C13—H13	120.4
C3—C4—C5	117.78 (18)	N2—C14—C13	122.92 (19)
C3—C4—C8	120.7 (2)	N2—C14—H14	118.5
C5—C4—C8	121.5 (2)	C13—C14—H14	118.5
C4—C5—C6	121.01 (19)	N3—C15—S1	179.04 (17)
C4—C5—H5	119.5
N3i—Cd1—N1—C9	−97.15 (13)	N1—C1—C2—C3	178.39 (16)
N3—Cd1—N1—C9	82.85 (13)	C6—C1—C2—C7	−179.92 (19)
N2i—Cd1—N1—C9	−7.89 (12)	N1—C1—C2—C7	−3.3 (3)
N2—Cd1—N1—C9	172.11 (12)	C1—C2—C3—C4	−0.7 (3)
N3i—Cd1—N1—C1	102.54 (13)	C7—C2—C3—C4	−179.06 (19)
N3—Cd1—N1—C1	−77.46 (13)	C2—C3—C4—C5	−0.7 (3)
N2i—Cd1—N1—C1	−168.21 (13)	C2—C3—C4—C8	179.22 (19)
N2—Cd1—N1—C1	11.79 (13)	C3—C4—C5—C6	1.0 (3)
N3i—Cd1—N2—C10	79.80 (12)	C8—C4—C5—C6	−178.9 (2)
N3—Cd1—N2—C10	−100.20 (12)	C4—C5—C6—C1	0.0 (3)
N1—Cd1—N2—C10	177.10 (12)	C2—C1—C6—C5	−1.4 (3)
N1i—Cd1—N2—C10	−2.90 (12)	N1—C1—C6—C5	−178.07 (16)
N3i—Cd1—N2—C14	−101.74 (16)	C1—N1—C9—C10i	173.99 (15)
N3—Cd1—N2—C14	78.26 (16)	Cd1—N1—C9—C10i	12.4 (2)
N1—Cd1—N2—C14	−4.44 (17)	C14—N2—C10—C11	−0.9 (3)
N1i—Cd1—N2—C14	175.56 (17)	Cd1—N2—C10—C11	177.80 (15)
N1—Cd1—N3—C15	7.1 (5)	C14—N2—C10—C9i	179.59 (16)
N1i—Cd1—N3—C15	−172.9 (5)	Cd1—N2—C10—C9i	−1.76 (19)
N2i—Cd1—N3—C15	79.2 (5)	N2—C10—C11—C12	0.5 (3)
N2—Cd1—N3—C15	−100.8 (5)	C9i—C10—C11—C12	−179.9 (2)
C9—N1—C1—C6	−57.6 (2)	C10—C11—C12—C13	−0.2 (3)
Cd1—N1—C1—C6	101.74 (16)	C11—C12—C13—C14	0.3 (3)
C9—N1—C1—C2	125.68 (18)	C10—N2—C14—C13	0.9 (3)
Cd1—N1—C1—C2	−74.95 (18)	Cd1—N2—C14—C13	−177.48 (15)
C6—C1—C2—C3	1.7 (3)	C12—C13—C14—N2	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···S1ii	0.93	2.87	3.591 (2)	136.

Table 1

Selected bond lengths (Å)

Cd1—N3	2.3032 (17)
Cd1—N1	2.3529 (14)
Cd1—N2	2.3708 (14)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯S1ii	0.93	2.87	3.591 (2)	136

Symmetry code: (ii) .