Dichlorido{(2E)-2-[phen­yl(pyridin-2-yl)methyl­idene]hydrazinecarbo­thio­amide}cadmium(II) methanol monosolvate

Aravindakshan, A.A.; Seena, V.; Sithambaresan, M.; Kurup, M.R.P.

doi:10.1107/S1600536814015694

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Pages m301-m302

doi:10.1107/S1600536814015694

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Dichlorido{(2E)-2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioamide}cadmium(II) methanol monosolvate

Ambili A. Aravindakshan,^a V. Seena,^a M. Sithambaresan ^b ^* and M. R. Prathapachandra Kurup ^a

^aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
^*Correspondence e-mail: msithambaresan@gmail.com

Edited by L. Farrugia, University of Glasgow, Scotland (Received 6 June 2014; accepted 5 July 2014; online 17 July 2014)

In the title compound, [CdCl₂(C₁₃H₁₂N₄S)]·CH₃OH, the coordination geometry of the Cd^II ion is slightly distorted square-pyramidal, as indicated by the τ index of 0.36 (8). The S atom, two N atoms from the pyridyl-azomethine moiety and one of the Cl atoms comprise the basal plane, while the other Cl atom occupies the apical position. The hydrazinecarbothioamide moiety adopts an E conformation with respect to the azomethine bond. The solvate molecule in the crystal lattice plays a major role in interconnecting adjacent molecules by means of O—H⋯Cl and N—H⋯O hydrogen-bonding interactions. A supramolecular three-dimensional architecture is sustained in terms of further N—H⋯Cl and C—H⋯Cl hydrogen-bonding interactions.

Keywords: crystal structure.

CCDC reference: 1012335

Related literature

For metal complexes of hydrazinecarbothioamide and its derivatives, see: Sreekanth et al. (2004 ). For applications of hydrazinecarbothioamides, see: Joseph et al. (2004 ); Kumar et al. (2011 , 2013 ). For the synthesis of related compounds, see: Philip et al. (2006 ). For related structures, see: Kunnath et al. (2012 ). For the calculation of the τ index, see: Addison et al. (1984 ).

Experimental

Crystal data

[CdCl₂(C₁₃H₁₂N₄S)]·CH₄O
M_r = 471.67
Monoclinic, P 2₁ /n
a = 7.7213 (4) Å
b = 12.9759 (8) Å
c = 18.3318 (11) Å
β = 95.248 (2)°
V = 1828.98 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.61 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.624, T_max = 0.725
13483 measured reflections
4392 independent reflections
3804 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.074
S = 0.99
4392 reflections
226 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1S	0.85 (1)	2.14 (2)	2.890 (3)	148 (2)
N4—H4B⋯Cl2ⁱ	0.84 (1)	2.43 (1)	3.253 (2)	167 (3)
N3—H3′⋯O1S	0.88 (1)	2.15 (2)	2.924 (3)	147 (3)
O1S—H1′⋯Cl1ⁱⁱ	0.85 (1)	2.40 (2)	3.201 (3)	158 (4)
C2—H2⋯Cl1ⁱⁱⁱ	0.93	2.80	3.680 (3)	159
Symmetry codes: (i) x+1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2008 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1012335

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814015694/fj2677sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015694/fj2677Isup2.hkl

checkCIF report

Comment top

The importance of hydrazinecarbothioamide is increasing in various fields due to its wide range of medicinal applications (Joseph et al., 2004) and structural diversity due to their variable coordinative abilities (Sreekanth et al., 2004) arising from thioamido-thioiminol tautomerism. Moreover it also found to serve as a corrosion inhibitor on mild steel in HCl (Kumar et al., 2011). Recently a new heterocyclic hydrazinecarbothioamide has been developed as colorimetric and turn on fluorescent sensors for fluoride anion (Kumar et al., 2013).

The title complex [C₁₃H₁₂CdCl₂N₄S]·(CH₄O) adopts an E configuration with respect to C6═N2 bond and the tridentate ligand has its coordinating entities disposed in a cis fashion to each other (Fig. 1). The Cd atom in the complex is N,N^',S chelated by the thioamido form of the hydrazinecarbothioamide ligand. The C6═N2 [1.278 (3) Å] and C13=S1 [1.690 (2) Å] bond distances, very close to the formal C═N and C═S bond lengths respectively confirm the azomethine bond formation and the coordination via thioamido form. The coordination geometry around Cd(II) ion is almost square pyramidal (Addison et al., 1984) with a slight distortion (τ = 0.36 (8)). The S1 atom of the hydrazinecarbothioamide moiety, the imino N2 atom, pyridine N1 atom and the Cl1 atom comprise the basal plane while the apical position is occupied by the Cl2 atom (Kunnath et al., 2012). However, the deviation from the ideal square pyramidal geometry is observed by the displacement of Cd atom from the basal plane and the trans angle of the basal atoms (Table 1).

There are four classical O–H···Cl, N–H···O and N–H···Cl and one non-classical C–H···Cl intermolecular hydrogen bonding interactions (Table 1, Fig. 2). Three of the classical interactions connect two neighbouring complexes through a solvate molecule with D···A distances of 3.201 (3), 2.924 (3) and 2.890 (3) Å. The other two classical and non-classical interactions directly connect two more neighbouring molecules directly to the main molecule with D···A distances of 3.253 (2) and 3.680 (3) Å respectively. These hydrogen bonding interactions build a double layer (Fig. 3) supramolecular chain along c axis. In addition to this, there are two very weak π···π interactions present with Cg···Cg distances of greater than 4 Å. Fig. 4 shows the packing diagram of the title compound along a axis.

Related literature top

For metal complexes of hydrazinecarbothioamide and its derivatives, see: Sreekanth et al. (2004). For applications of hydrazinecarbothioamides, see: Joseph et al. (2004); Kumar et al. (2011, 2013). For the synthesis of related compounds, see: Philip et al. (2006). For related structures, see: Kunnath et al. (2012). For the calculation of the τ index, see: Addison et al. (1984).

Experimental top

The potentialy tridentate ligand (2E)-2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioamide was synthesized in situ by mixing equimolar methanolic solutions of phenyl(pyridin-2-yl)methanone (0.0916 g, 0.5 mmol), hydrazinecarbothioamide (0.0455 g, 0.5 mmol) and 5 drops of glacial acetic acid for 2 h. The title complex was prepared by adapting a reported procedure (Philip et al., 2006) by refluxing the above ligand solution and CdCl₂·2.5H₂O (0.1141 g, 0.5 mmol) for 3 h. The resulting solution was cooled at room temperature. Upon slow evaporation, yellow coloured product formed were collected, washed with few drops of methanol and dried over P₄O₁₀ in vacuo. Yellow blocked shaped single crystals of the title compound suitable for X-ray analysis were obtained by recrystallization from methanol. The compound was obtained in 56%, yield (0.1320 g).

IR (KBr, \v in cm^-1): 3439, 3225, 3125, 1603, 1380, 1314, 1213, 1147, 780, 659, 560.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2008 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP view of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms.
	Fig. 2. Graphical representation showing hydrogen bonding interactions in the crystal structure of [C₁₃H₁₂CdCl₂N₄S]·(CH₄O).
	Fig. 3. The hydrogen bonding interactions build a double layer progressing along c axis in the title compound.
	Fig. 4. A view of the unit cell along a axis.

Dichlorido{(2E)-2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioamide}cadmium(II) methanol monosolvate top

Crystal data top

[CdCl₂(C₁₃H₁₂N₄S)]·CH₄O	F(000) = 936
M_r = 471.67	D_x = 1.713 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7213 (4) Å	Cell parameters from 8955 reflections
b = 12.9759 (8) Å	θ = 2.7–28.1°
c = 18.3318 (11) Å	µ = 1.61 mm⁻¹
β = 95.248 (2)°	T = 293 K
V = 1828.98 (18) Å³	Block, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4392 independent reflections
Radiation source: fine-focus sealed tube	3804 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	R_int = 0.031
ω and ϕ scan	θ_max = 28.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→10
T_min = 0.624, T_max = 0.725	k = −17→13
13483 measured reflections	l = −24→24

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.028	w = 1/[σ²(F_o²) + (0.0364P)² + 1.2328P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.074	(Δ/σ)_max = 0.001
S = 0.99	Δρ_max = 0.50 e Å⁻³
4392 reflections	Δρ_min = −0.60 e Å⁻³
226 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
5 restraints	Extinction coefficient: 0.0143 (5)

Crystal data top

[CdCl₂(C₁₃H₁₂N₄S)]·CH₄O	V = 1828.98 (18) Å³
M_r = 471.67	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.7213 (4) Å	µ = 1.61 mm⁻¹
b = 12.9759 (8) Å	T = 293 K
c = 18.3318 (11) Å	0.30 × 0.25 × 0.20 mm
β = 95.248 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4392 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3804 reflections with I > 2σ(I)
T_min = 0.624, T_max = 0.725	R_int = 0.031
13483 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	5 restraints
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.50 e Å⁻³
4392 reflections	Δρ_min = −0.60 e Å⁻³
226 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6778 (3)	−0.0088 (2)	0.60386 (14)	0.0421 (6)
H1	0.6464	0.0012	0.5542	0.050*
C1S	1.5904 (6)	0.1528 (4)	0.8959 (2)	0.0876 (14)
H1S1	1.7000	0.1843	0.9116	0.131*
H1S2	1.6102	0.0858	0.8762	0.131*
H1S3	1.5223	0.1463	0.9369	0.131*
C2	0.5687 (3)	−0.0651 (2)	0.64401 (17)	0.0507 (7)
H2	0.4663	−0.0931	0.6218	0.061*
C3	0.6140 (4)	−0.0790 (3)	0.71739 (17)	0.0526 (7)
H3	0.5415	−0.1157	0.7458	0.063*
C4	0.7687 (3)	−0.0379 (2)	0.74891 (15)	0.0416 (6)
H4	0.8021	−0.0473	0.7985	0.050*
C5	0.8727 (3)	0.01721 (18)	0.70534 (12)	0.0314 (4)
C6	1.0420 (3)	0.06173 (18)	0.73536 (12)	0.0306 (4)
C7	1.0948 (3)	0.05746 (19)	0.81515 (12)	0.0330 (5)
C8	1.0602 (4)	0.1385 (2)	0.85957 (16)	0.0522 (7)
H8	1.0030	0.1965	0.8397	0.063*
C9	1.1105 (5)	0.1341 (3)	0.93427 (17)	0.0629 (9)
H9	1.0881	0.1895	0.9642	0.075*
C10	1.1920 (5)	0.0491 (3)	0.96346 (16)	0.0654 (9)
H10	1.2226	0.0455	1.0137	0.078*
C11	1.2297 (5)	−0.0314 (3)	0.91957 (18)	0.0739 (11)
H11	1.2879	−0.0889	0.9399	0.089*
C12	1.1816 (4)	−0.0279 (2)	0.84519 (16)	0.0557 (7)
H12	1.2075	−0.0827	0.8154	0.067*
C13	1.3920 (3)	0.18172 (19)	0.65912 (12)	0.0330 (5)
N1	0.8267 (2)	0.03206 (16)	0.63337 (10)	0.0334 (4)
N2	1.1338 (2)	0.10222 (16)	0.68830 (10)	0.0319 (4)
N3	1.2894 (3)	0.14580 (17)	0.71024 (11)	0.0361 (5)
S1	1.33814 (8)	0.17757 (6)	0.56772 (3)	0.03929 (15)
Cl1	0.87665 (9)	0.10250 (6)	0.44174 (3)	0.04381 (16)
Cl2	0.88268 (9)	0.29835 (6)	0.61058 (4)	0.04826 (16)
Cd1	1.00948 (2)	0.13266 (2)	0.56724 (2)	0.03757 (8)
O1S	1.5008 (3)	0.2144 (2)	0.84178 (12)	0.0690 (7)
N4	1.5417 (3)	0.2202 (2)	0.68671 (12)	0.0442 (5)
H3'	1.326 (4)	0.147 (2)	0.7569 (7)	0.051 (9)*
H1'	1.469 (6)	0.2722 (18)	0.857 (2)	0.094 (15)*
H4A	1.572 (3)	0.227 (2)	0.7320 (6)	0.041 (8)*
H4B	1.618 (3)	0.244 (2)	0.6613 (12)	0.049 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0354 (12)	0.0465 (15)	0.0425 (13)	−0.0005 (11)	−0.0063 (10)	−0.0023 (11)
C1S	0.072 (3)	0.121 (4)	0.068 (2)	0.026 (2)	−0.006 (2)	−0.008 (2)
C2	0.0336 (13)	0.0547 (17)	0.0611 (17)	−0.0111 (12)	−0.0094 (11)	0.0044 (14)
C3	0.0382 (14)	0.0572 (18)	0.0623 (17)	−0.0142 (12)	0.0041 (12)	0.0157 (15)
C4	0.0363 (12)	0.0457 (14)	0.0422 (12)	−0.0057 (10)	0.0008 (10)	0.0085 (11)
C5	0.0290 (10)	0.0334 (12)	0.0317 (10)	−0.0004 (9)	0.0019 (8)	−0.0002 (9)
C6	0.0304 (10)	0.0323 (11)	0.0290 (10)	−0.0006 (9)	0.0018 (8)	0.0000 (9)
C7	0.0327 (11)	0.0383 (13)	0.0280 (10)	−0.0060 (9)	0.0018 (8)	0.0016 (9)
C8	0.0618 (18)	0.0534 (18)	0.0414 (14)	0.0111 (13)	0.0053 (13)	−0.0063 (12)
C9	0.077 (2)	0.074 (2)	0.0386 (15)	−0.0028 (17)	0.0085 (14)	−0.0200 (15)
C10	0.084 (2)	0.079 (2)	0.0308 (13)	−0.0169 (19)	−0.0070 (14)	0.0060 (15)
C11	0.109 (3)	0.062 (2)	0.0453 (17)	0.004 (2)	−0.0225 (18)	0.0132 (15)
C12	0.079 (2)	0.0440 (16)	0.0415 (14)	0.0086 (15)	−0.0104 (13)	−0.0027 (12)
C13	0.0301 (11)	0.0344 (12)	0.0350 (11)	−0.0020 (9)	0.0055 (9)	−0.0026 (9)
N1	0.0307 (9)	0.0377 (11)	0.0312 (9)	−0.0007 (8)	−0.0005 (7)	−0.0020 (8)
N2	0.0271 (9)	0.0381 (10)	0.0299 (9)	−0.0059 (8)	−0.0004 (7)	−0.0006 (8)
N3	0.0295 (10)	0.0521 (13)	0.0261 (9)	−0.0099 (8)	−0.0006 (7)	−0.0007 (8)
S1	0.0343 (3)	0.0535 (4)	0.0306 (3)	−0.0059 (3)	0.0057 (2)	0.0016 (3)
Cl1	0.0462 (3)	0.0522 (4)	0.0309 (3)	0.0028 (3)	−0.0080 (2)	−0.0044 (3)
Cl2	0.0479 (4)	0.0491 (4)	0.0494 (3)	0.0008 (3)	0.0134 (3)	−0.0027 (3)
Cd1	0.03411 (11)	0.05315 (14)	0.02497 (10)	−0.00521 (7)	0.00006 (6)	0.00039 (7)
O1S	0.0751 (15)	0.091 (2)	0.0399 (11)	0.0034 (14)	0.0001 (10)	−0.0176 (12)
N4	0.0326 (11)	0.0592 (15)	0.0409 (11)	−0.0146 (10)	0.0046 (9)	−0.0074 (11)

Geometric parameters (Å, º) top

C1—N1	1.334 (3)	C9—C10	1.356 (5)
C1—C2	1.378 (4)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.366 (5)
C1S—O1S	1.405 (5)	C10—H10	0.9300
C1S—H1S1	0.9600	C11—C12	1.381 (4)
C1S—H1S2	0.9600	C11—H11	0.9300
C1S—H1S3	0.9600	C12—H12	0.9300
C2—C3	1.370 (4)	C13—N4	1.317 (3)
C2—H2	0.9300	C13—N3	1.363 (3)
C3—C4	1.385 (4)	C13—S1	1.690 (2)
C3—H3	0.9300	N1—Cd1	2.341 (2)
C4—C5	1.383 (3)	N2—N3	1.356 (3)
C4—H4	0.9300	N2—Cd1	2.3690 (19)
C5—N1	1.349 (3)	N3—H3'	0.876 (10)
C5—C6	1.488 (3)	S1—Cd1	2.6030 (6)
C6—N2	1.278 (3)	Cl1—Cd1	2.4630 (6)
C6—C7	1.483 (3)	Cl2—Cd1	2.5208 (7)
C7—C8	1.371 (4)	O1S—H1'	0.846 (10)
C7—C12	1.382 (4)	N4—H4A	0.845 (9)
C8—C9	1.390 (4)	N4—H4B	0.841 (10)
C8—H8	0.9300

N1—C1—C2	122.7 (2)	C11—C10—H10	119.8
N1—C1—H1	118.7	C10—C11—C12	120.2 (3)
C2—C1—H1	118.7	C10—C11—H11	119.9
O1S—C1S—H1S1	109.5	C12—C11—H11	119.9
O1S—C1S—H1S2	109.5	C11—C12—C7	119.8 (3)
H1S1—C1S—H1S2	109.5	C11—C12—H12	120.1
O1S—C1S—H1S3	109.5	C7—C12—H12	120.1
H1S1—C1S—H1S3	109.5	N4—C13—N3	114.2 (2)
H1S2—C1S—H1S3	109.5	N4—C13—S1	121.38 (18)
C3—C2—C1	118.7 (2)	N3—C13—S1	124.39 (17)
C3—C2—H2	120.7	C1—N1—C5	118.7 (2)
C1—C2—H2	120.7	C1—N1—Cd1	123.32 (17)
C2—C3—C4	119.5 (3)	C5—N1—Cd1	117.97 (14)
C2—C3—H3	120.3	C6—N2—N3	120.16 (19)
C4—C3—H3	120.3	C6—N2—Cd1	119.91 (15)
C5—C4—C3	118.8 (2)	N3—N2—Cd1	118.72 (14)
C5—C4—H4	120.6	N2—N3—C13	119.59 (19)
C3—C4—H4	120.6	N2—N3—H3'	120 (2)
N1—C5—C4	121.6 (2)	C13—N3—H3'	121 (2)
N1—C5—C6	116.77 (19)	C13—S1—Cd1	99.32 (8)
C4—C5—C6	121.6 (2)	N1—Cd1—N2	68.51 (6)
N2—C6—C7	124.2 (2)	N1—Cd1—Cl1	100.12 (5)
N2—C6—C5	115.62 (19)	N2—Cd1—Cl1	161.25 (6)
C7—C6—C5	120.20 (19)	N1—Cd1—Cl2	92.43 (5)
C8—C7—C12	119.4 (2)	N2—Cd1—Cl2	89.01 (5)
C8—C7—C6	120.4 (2)	Cl1—Cd1—Cl2	106.82 (2)
C12—C7—C6	120.2 (2)	N1—Cd1—S1	139.20 (5)
C7—C8—C9	120.1 (3)	N2—Cd1—S1	73.91 (5)
C7—C8—H8	120.0	Cl1—Cd1—S1	111.18 (2)
C9—C8—H8	120.0	Cl2—Cd1—S1	102.39 (2)
C10—C9—C8	120.0 (3)	C1S—O1S—H1'	114 (3)
C10—C9—H9	120.0	C13—N4—H4A	124.5 (17)
C8—C9—H9	120.0	C13—N4—H4B	124.1 (18)
C9—C10—C11	120.4 (3)	H4A—N4—H4B	111 (2)
C9—C10—H10	119.8

N1—C1—C2—C3	0.6 (5)	C8—C7—C12—C11	1.2 (5)
C1—C2—C3—C4	−1.1 (5)	C6—C7—C12—C11	−179.7 (3)
C2—C3—C4—C5	0.7 (5)	C2—C1—N1—C5	0.3 (4)
C3—C4—C5—N1	0.2 (4)	C2—C1—N1—Cd1	−177.9 (2)
C3—C4—C5—C6	−178.9 (3)	C4—C5—N1—C1	−0.7 (4)
N1—C5—C6—N2	−5.7 (3)	C6—C5—N1—C1	178.4 (2)
C4—C5—C6—N2	173.4 (2)	C4—C5—N1—Cd1	177.54 (19)
N1—C5—C6—C7	174.3 (2)	C6—C5—N1—Cd1	−3.3 (3)
C4—C5—C6—C7	−6.6 (4)	C7—C6—N2—N3	−0.6 (4)
N2—C6—C7—C8	86.1 (3)	C5—C6—N2—N3	179.3 (2)
C5—C6—C7—C8	−93.9 (3)	C7—C6—N2—Cd1	−167.91 (17)
N2—C6—C7—C12	−93.0 (3)	C5—C6—N2—Cd1	12.1 (3)
C5—C6—C7—C12	87.0 (3)	C6—N2—N3—C13	175.0 (2)
C12—C7—C8—C9	−0.7 (5)	Cd1—N2—N3—C13	−17.5 (3)
C6—C7—C8—C9	−179.8 (3)	N4—C13—N3—N2	−178.5 (2)
C7—C8—C9—C10	−0.8 (5)	S1—C13—N3—N2	0.8 (3)
C8—C9—C10—C11	1.8 (6)	N4—C13—S1—Cd1	−167.7 (2)
C9—C10—C11—C12	−1.4 (6)	N3—C13—S1—Cd1	13.1 (2)
C10—C11—C12—C7	−0.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1S	0.85 (1)	2.14 (2)	2.890 (3)	148 (2)
N4—H4B···Cl2ⁱ	0.84 (1)	2.43 (1)	3.253 (2)	167 (3)
N3—H3′···O1S	0.88 (1)	2.15 (2)	2.924 (3)	147 (3)
O1S—H1′···Cl1ⁱⁱ	0.85 (1)	2.40 (2)	3.201 (3)	158 (4)
C2—H2···Cl1ⁱⁱⁱ	0.93	2.80	3.680 (3)	159

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1S	0.845 (9)	2.139 (15)	2.890 (3)	148 (2)
N4—H4B···Cl2ⁱ	0.841 (10)	2.427 (12)	3.253 (2)	167 (3)
N3—H3'···O1S	0.876 (10)	2.15 (2)	2.924 (3)	147 (3)
O1S—H1'···Cl1ⁱⁱ	0.846 (10)	2.40 (2)	3.201 (3)	158 (4)
C2—H2···Cl1ⁱⁱⁱ	0.9300	2.80	3.680 (3)	159

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1.

Acknowledgements

AAA is grateful to the Council for Scientific and Industrial Research, New Delhi, India for the award of a Senior Research Fellowship. MRPK thanks the University Grants Commission, New Delhi, for a UGC–BSR one-time grant to faculty. We thank the Sophisticated Analytical Instruments Facility, Cochin University of S & T, Kochi-22, India, for the diffraction measurements and FT–IR studies.

References

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Volume 70| Part 8| August 2014| Pages m301-m302

doi:10.1107/S1600536814015694

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­chlorido{(2E)-2-[phen­yl(pyridin-2-yl)methyl­­idene]hydrazinecarbo­thio­amide}cadmium(II) methanol monosolvate

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Experimental

Crystal data

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metal-organic compounds

Dichlorido{(2E)-2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioamide}cadmium(II) methanol monosolvate