Bis{2-[(2,4-dimethyl­phen­yl)imino­meth­yl]pyridine-κ2N,N′}bis­(thio­cyanato-κN)cadmium

Malekshahian, M.; Talei Bavil Olyai, M.R.; Notash, B.

doi:10.1107/S1600536812002772

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m218-m219

doi:10.1107/S1600536812002772

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Bis{2-[(2,4-dimethylphenyl)iminomethyl]pyridine-κ²N,N′}bis(thiocyanato-κN)cadmium

Mohammad Malekshahian,^a Mohamad Reza Talei Bavil Olyai ^b ^* and Behrouz Notash ^c

^aDepartment of Chemistry, Islamic Azad University, Karaj Branch, Karaj, Iran, ^bDepartment of Chemistry, Faculty of Science, Islamic Azad University, South Tehran Branch, Tehran, Iran, and ^cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: talei3@gmail.com

(Received 15 January 2012; accepted 22 January 2012; online 31 January 2012)

The title compound, [Cd(NCS)₂(C₁₄H₁₄N₂)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 octahedral geometry with the thiocyanate anions in axial positions. The angle between the benzene and pyridine rings is 69.64 (9)°. An intermolecular 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_r = 649.13
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.025
wR(F²) = 0.075
S = 1.00
4016 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N3	2.3032 (17)
Cd1—N1	2.3529 (14)
Cd1—N2	2.3708 (14)
Symmetry code: (i) -x+1, -y, -z+1.

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) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812002772/bt5786sup1.cif

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

checkCIF report

Comment top

Nitrogen donor ligands particularly Schiff bases have been a subject of interest for chemists. Schiff bases form a class of compounds with azomethine group, which are usually synthesized from the condensation of primary amines and active carbonyl groups by elimination of water molecule. The Schiff bases and their metal complexes are important class of compounds in medicinal and pharmaceutical field (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).

Following our studies on the synthesis and structural determination of transition metal complexes with iminopyridine ligands by X-ray crystallography (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). We report herein the crystal structure of the title compound, a new cadmium(II) complex, (1), derived from the Schiff base ligand and thiocyanate. The title complex was synthesized by the reaction of Cd(CH₃COO)₂.2H₂O with 2-[(2,4-dimethylphenyl)iminomethyl]- pyridine and KSCN in methanol as solution.

In the crystal structure of the title compound (Fig. 1), the cadmium(II) ion is six-coordinated in distorted octahedral geometry. Two Schiff base ligands coordinate the cadmium center as a bidentate ligand through the nitrogen atoms of imine group and pyridine ring. The Cd(II) ion is soft acidic metal center. According to symbiosis logic of Jorgensen, coordination of four electronegative nitrogen atoms of iminopyridine ligands have increased hardness of the cadmium ion and makes it a hard Lewis acid. Therefore, the Cd(II) ion prefers to bond to nitrogen atom of the ambidentate thiocyanate ligand.

The Cd—N_thiocyanate distances [2.3032 (17) Å] are notably shorter than the Cd—N_imine distances [2.3529 (1) Å] and Cd—N_pyridine [2.3708 (14) Å] (Table 1). The two imine linkages, C9—N1 [1.268 (2) Å], are both short, which is in the accepted range for carbon-nitrogen double bonds. Four donor nitrogen atoms of the iminopyridine ligands are absolutely planar with the Cadmium(II). In the title compound, coordination plane (containing the ligands backbone and the cadmium atom), and two thiocyanate ions are trans to each other. The angle between phenyl and pyridine rings are 69.64 (9) Å. In the crystal structure of the title compound an intermolecular C—H···S hydrogen bond (Table 2) stabilize crystal structure.

Related literature top

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 structure 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 top

For the preparation of the title compound, a mixed solution of 2-[(2,4-dimethylphenyl)-iminomethyl]-pyridine (0.420 g, 2.00 mmol) and KSCN (0.195 g 2.00 mmol) in methanol (10 ml) was added slowly to a solution of Cd(CH₃COO)₂.2H₂O (0.267 g, 1.00 mmol) in methanol (10 ml) and the resulting yellow solution was stirred for 45 min at room temperature, and then left to evaporate slowly at 3–5°C. After twenty days, yellow crystals of the title compound were isolated (yield; 0.426 g, 74.2%, m. p. 453 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code:(a)-x + 1, -y, -z + 1].
	Fig. 2. Packing diagram of the title compound showing intermolecular C—H···S hydrogen bonding.

Bis{2-[(2,4-dimethylphenyl)iminomethyl]pyridine- κ²N,N'}bis(thiocyanato-κN)cadmium top

Crystal data top

[Cd(NCS)₂(C₁₄H₁₄N₂)₂]	F(000) = 1320.0
M_r = 649.13	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0406P)² + 0.0706P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
4016 reflections	Δρ_max = 0.20 e Å⁻³
181 parameters	Δρ_min = −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)

Crystal data top

[Cd(NCS)₂(C₁₄H₁₄N₂)₂]	V = 2984.7 (10) Å³
M_r = 649.13	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 11.285 (2) Å	µ = 0.90 mm⁻¹
b = 15.048 (3) Å	T = 298 K
c = 17.576 (4) Å	0.45 × 0.4 × 0.4 mm

Data collection top

Stoe IPDS II diffractometer	4016 independent reflections
Absorption correction: numerical shape of crystal determined optically	2589 reflections with I > 2σ(I)
T_min = 0.406, T_max = 0.430	R_int = 0.028
12952 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
4016 reflections	Δρ_min = −0.39 e Å⁻³
181 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	0.5000	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Cd(NCS)₂(C₁₄H₁₄N₂)₂]
M_r	649.13
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	11.285 (2), 15.048 (3), 17.576 (4)
V (Å³)	2984.7 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.45 × 0.4 × 0.4

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Numerical shape of crystal determined optically
T_min, T_max	0.406, 0.430
No. of measured, independent and observed [I > 2σ(I)] reflections	12952, 4016, 2589
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.075, 1.00
No. of reflections	4016
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.39

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Cd1—N3	2.3032 (17)	Cd1—N2	2.3708 (14)
Cd1—N1	2.3529 (14)	N1—C9	1.268 (2)

N3ⁱ—Cd1—N3	180.0	N3ⁱ—Cd1—N2ⁱ	91.58 (6)
N3ⁱ—Cd1—N1	97.43 (6)	N1—Cd1—N2	107.97 (5)
N3—Cd1—N1	82.57 (6)	N2ⁱ—Cd1—N2	180.0
N1—Cd1—N1ⁱ	180.00 (5)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···S1ⁱⁱ	0.9300	2.8700	3.591 (2)	136.00

Symmetry code: (ii) −x+3/2, −y+1/2, z+1/2.

Acknowledgements

The authors acknowledge Islamic Azad University, Karaj Branch, for financial support.

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