Bis[N-(2-hy­droxy­eth­yl)-N-propyl­dithio­carbamato-κ2S,S′]bis­(4-{[(pyridin-4-yl­methyl­idene)hydrazinyl­idene]meth­yl}pyridine-κN1)cadmium

Broker, G.A.; Tiekink, E.R.T.

doi:10.1107/S1600536811004508

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages m320-m321

doi:10.1107/S1600536811004508

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Bis[N-(2-hydroxyethyl)-N-propyldithiocarbamato-κ²S,S′]bis(4-{[(pyridin-4-ylmethylidene)hydrazinylidene]methyl}pyridine-κN¹)cadmium

Grant A. Broker ^a and Edward R. T. Tiekink ^b ^*

^a5959 FM 1960 Road West, Houston, Texas 77069, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 28 January 2011; accepted 7 February 2011; online 12 February 2011)

The complete molecule of the title compound, [Cd(C₆H₁₂NOS₂)₂(C₁₂H₁₀N₄)₂], is generated by crystallographic inversion symmetry. The distorted octahedral trans-N₂S₄ donor set for the Cd²⁺ ion is defined by two symmetrically S,S′-chelating dithiocarbamate anions and two pyridine N atoms derived from two monodentate 4-pyridinealdazine (or 4-{[(pyridin-4-ylmethylidene)hydrazinylidene}methyl]pyridine) molecules [dihedral angle between the aromatic rings = 17.33 (8)°]. In the crystal, molecules are connected into a supramolecular chain via O—H⋯N hydrogen bonds involving the 4-pyridinealdazine N atoms not involved in coordination to cadmium. Weak C—H⋯O and C—H⋯N links consolidate the packing.

Related literature

For background to supramolecular coordination polymers of zinc-triad 1,1-dithiolates, see: Tiekink (2003 ). For the use of steric effects to control supramolecular aggregation patterns, see: Chen et al. (2006 ). For structural studies on hydroxyl-substituted dithiocarbamate ligands, see Benson et al. (2007 ); Song & Tiekink (2009 ).

Experimental

Crystal data

[Cd(C₆H₁₂NOS₂)₂(C₁₂H₁₀N₄)₂]
M_r = 889.45
Triclinic, $[P \overline 1]$
a = 8.532 (3) Å
b = 10.951 (4) Å
c = 11.184 (5) Å
α = 79.59 (3)°
β = 88.06 (3)°
γ = 78.23 (2)°
V = 1006.2 (7) Å³
Z = 1
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 98 K
0.25 × 0.16 × 0.04 mm

Data collection

Rigaku AFC12/SATURN724 CCD diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.719, T_max = 1
10677 measured reflections
4150 independent reflections
4009 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.062
S = 1.08
4150 reflections
245 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cd—S1	2.6379 (10)
Cd—S2	2.6626 (10)
Cd—N2	2.5403 (17)

S1—Cd—S2	68.83 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N5ⁱ	0.84 (2)	1.98 (2)	2.810 (2)	176 (2)
C10—H10⋯O1ⁱⁱ	0.95	2.55	3.480 (3)	168
C3—H3a⋯N4ⁱⁱⁱ	0.99	2.61	3.369 (3)	134
Symmetry codes: (i) x+2, y, z-1; (ii) -x+1, -y, -z+1; (iii) x+1, y, z-1.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: PATTY in DIRDIF (Beurskens et al., 1992 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPII (Johnson, 1976 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004508/hb5795sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004508/hb5795Isup2.hkl

checkCIF report

Comment top

Interest in the title compound, (I), relates to controlling supramolecular aggregation patterns in the zinc-triad 1,1-thiolates (Tiekink, 2003; Chen et al., 2006). With functionalized dithiocarbamate ligands carrying hydrogen bonding potential, smaller aggregates can be linked into 2-D and 3-D architectures (Benson et al., 2007; Song & Tiekink, 2009). In (I), the cadmium atom is located on a centre of inversion and is chelated by symmetrically coordinating dithiocarbamate ligands, Table 1 and Fig. 1. The octahedral N₂S₄ donor set is completed by two pyridine-N atoms derived from two monodentate 4-pyridinealdazine ligands.

The monomeric molecules are connected into a supramolecular chain via O–H···N hydrogen bonds, Table 2, that lead to the formation of 40-membered [CdSCNC₂OH···NC₄N₂C₄N]₂ synthons, Fig. 2. These chains are linked into layers via C–H···O interactions, Table 1, which that stack along [1 0 1]; consolidation of these layers into a 3-D array is afforded by C—H···N_azo contacts, Table 2 and Fig. 3.

Related literature top

For background to supramolecular coordination polymers of zinc-triad 1,1-dithiolates, see: Tiekink (2003). For the use of steric effects to control supramolecular aggregation patterns, see: Chen et al. (2006). For structural studies on hydroxyl-substituted dithiocarbamate ligands, see Benson et al. (2007); Song & Tiekink (2009).

Experimental top

Compound (I) was prepared following the standard literature procedure (Song & Tiekink, 2009) from the reaction of Cd[S₂CN(CH₂CH₂OH)(nPr)]₂ and 4-[(1E)-[(E)-2-(pyridin-4-ylmethylidene)hydrazin-1-ylidene]methyl]pyridine (Sigma Aldrich). Yellow plates of (I) were obtained from the slow evaporation of a chloroform/acetonitrile (3/1) solution.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: PATTY in DIRDIF (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of (I) showing displacement ellipsoids at the 70% probability level. The Cd atom is located on a centre of inversion and i = 1 - x, 1 - y, 1 - z.
	Fig. 2. Supramolecular chain in (I) mediated by O–H···N (orange dashed lines) hydrogen bonds. Colour code: Cd, orange; S, yellow; O, red; N, blue; C, grey; and H, green.
	Fig. 3. Unit-cell contents in (I) viewed in projection down the a axis.

Bis[N-(2-hydroxyethyl)-N-propyldithiocarbamato- κ²S,S']bis(4-{[(pyridin-4- ylmethylidene)hydrazinylidene]methyl}pyridine-κN¹)cadmium top

Crystal data top

[Cd(C₆H₁₂NOS₂)₂(C₁₂H₁₀N₄)₂]	Z = 1
M_r = 889.45	F(000) = 458
Triclinic, P1	D_x = 1.468 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 8.532 (3) Å	Cell parameters from 3485 reflections
b = 10.951 (4) Å	θ = 2.4–30.3°
c = 11.184 (5) Å	µ = 0.80 mm⁻¹
α = 79.59 (3)°	T = 98 K
β = 88.06 (3)°	Plate, yellow
γ = 78.23 (2)°	0.25 × 0.16 × 0.04 mm
V = 1006.2 (7) Å³

Data collection top

Rigaku AFC12K/SATURN724 CCD diffractometer	4150 independent reflections
Radiation source: fine-focus sealed tube	4009 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 26.5°, θ_min = 2.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.719, T_max = 1	k = −13→12
10677 measured reflections	l = −14→14

Refinement top

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) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0288P)² + 0.6008P] where P = (F_o² + 2F_c²)/3
4150 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.40 e Å⁻³
1 restraint	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Cd(C₆H₁₂NOS₂)₂(C₁₂H₁₀N₄)₂]	γ = 78.23 (2)°
M_r = 889.45	V = 1006.2 (7) Å³
Triclinic, P1	Z = 1
a = 8.532 (3) Å	Mo Kα radiation
b = 10.951 (4) Å	µ = 0.80 mm⁻¹
c = 11.184 (5) Å	T = 98 K
α = 79.59 (3)°	0.25 × 0.16 × 0.04 mm
β = 88.06 (3)°

Data collection top

Rigaku AFC12K/SATURN724 CCD diffractometer	4150 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4009 reflections with I > 2σ(I)
T_min = 0.719, T_max = 1	R_int = 0.023
10677 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	1 restraint
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.40 e Å⁻³
4150 reflections	Δρ_min = −0.40 e Å⁻³
245 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cd	0.5000	0.5000	0.5000	0.01706 (6)
S1	0.67567 (5)	0.26992 (4)	0.55937 (3)	0.01562 (9)
S2	0.48740 (5)	0.36286 (4)	0.32801 (4)	0.01587 (9)
O1	0.88422 (15)	0.05660 (12)	0.17754 (11)	0.0223 (3)
H1o	0.954 (2)	0.094 (2)	0.1432 (19)	0.033*
N1	0.67484 (15)	0.13324 (12)	0.38469 (11)	0.0120 (3)
N2	0.26143 (17)	0.42763 (14)	0.61140 (13)	0.0192 (3)
N3	−0.25800 (17)	0.36129 (14)	0.82625 (13)	0.0194 (3)
N4	−0.37162 (17)	0.28924 (14)	0.87834 (12)	0.0191 (3)
N5	−0.88990 (18)	0.19365 (15)	1.06431 (14)	0.0245 (3)
C1	0.61822 (18)	0.24449 (15)	0.41986 (14)	0.0135 (3)
C2	0.62455 (19)	0.10536 (15)	0.26935 (14)	0.0156 (3)
H2A	0.5139	0.1526	0.2501	0.019*
H2B	0.6239	0.0138	0.2796	0.019*
C3	0.7325 (2)	0.14035 (16)	0.16368 (15)	0.0196 (3)
H3A	0.6824	0.1356	0.0866	0.024*
H3B	0.7465	0.2285	0.1601	0.024*
C4	0.79259 (19)	0.03218 (15)	0.45840 (14)	0.0150 (3)
H4A	0.8604	0.0717	0.5037	0.018*
H4B	0.8630	−0.0158	0.4033	0.018*
C5	0.7154 (2)	−0.05962 (16)	0.54826 (15)	0.0185 (3)
H5A	0.6421	−0.0957	0.5043	0.022*
H5B	0.6517	−0.0137	0.6080	0.022*
C6	0.8430 (2)	−0.16666 (17)	0.61485 (17)	0.0239 (4)
H6A	0.7911	−0.2254	0.6715	0.036*
H6B	0.9137	−0.1311	0.6602	0.036*
H6C	0.9059	−0.2121	0.5557	0.036*
C7	0.1257 (2)	0.50814 (17)	0.63223 (18)	0.0254 (4)
H7	0.1197	0.5963	0.6049	0.031*
C8	−0.0057 (2)	0.46933 (17)	0.69130 (17)	0.0238 (4)
H8	−0.0989	0.5297	0.7041	0.029*
C9	0.0008 (2)	0.34018 (16)	0.73174 (14)	0.0169 (3)
C10	0.1403 (2)	0.25663 (16)	0.70970 (16)	0.0203 (3)
H10	0.1493	0.1679	0.7352	0.024*
C11	0.2661 (2)	0.30418 (16)	0.65018 (16)	0.0205 (3)
H11	0.3608	0.2458	0.6362	0.025*
C12	−0.1326 (2)	0.28869 (16)	0.79403 (14)	0.0177 (3)
H12	−0.1255	0.1995	0.8107	0.021*
C13	−0.5012 (2)	0.35972 (17)	0.90688 (15)	0.0200 (3)
H13	−0.5119	0.4492	0.8929	0.024*
C14	−0.6338 (2)	0.30118 (17)	0.96168 (14)	0.0188 (3)
C15	−0.7640 (2)	0.37321 (18)	1.01209 (17)	0.0248 (4)
H15	−0.7681	0.4604	1.0127	0.030*
C16	−0.8877 (2)	0.31554 (19)	1.06143 (17)	0.0269 (4)
H16	−0.9762	0.3659	1.0952	0.032*
C17	−0.7628 (2)	0.12403 (18)	1.01712 (16)	0.0247 (4)
H17	−0.7612	0.0367	1.0192	0.030*
C18	−0.6341 (2)	0.17338 (18)	0.96559 (16)	0.0228 (4)
H18	−0.5468	0.1206	0.9332	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.01757 (10)	0.01303 (10)	0.02083 (10)	−0.00255 (7)	0.00354 (7)	−0.00493 (7)
S1	0.0170 (2)	0.01481 (19)	0.01487 (19)	−0.00153 (15)	−0.00065 (15)	−0.00389 (15)
S2	0.0170 (2)	0.01234 (19)	0.0169 (2)	−0.00014 (15)	−0.00203 (15)	−0.00179 (15)
O1	0.0183 (6)	0.0224 (6)	0.0251 (6)	−0.0043 (5)	0.0080 (5)	−0.0026 (5)
N1	0.0114 (6)	0.0119 (6)	0.0122 (6)	−0.0014 (5)	−0.0004 (5)	−0.0016 (5)
N2	0.0185 (7)	0.0181 (7)	0.0218 (7)	−0.0050 (6)	0.0034 (6)	−0.0048 (6)
N3	0.0178 (7)	0.0218 (7)	0.0184 (7)	−0.0064 (6)	0.0024 (5)	−0.0007 (6)
N4	0.0188 (7)	0.0228 (7)	0.0161 (7)	−0.0080 (6)	0.0024 (5)	−0.0003 (6)
N5	0.0222 (8)	0.0305 (9)	0.0219 (8)	−0.0094 (7)	0.0047 (6)	−0.0035 (6)
C1	0.0114 (7)	0.0144 (8)	0.0147 (7)	−0.0042 (6)	0.0032 (6)	−0.0014 (6)
C2	0.0165 (8)	0.0145 (8)	0.0158 (8)	−0.0018 (6)	0.0002 (6)	−0.0037 (6)
C3	0.0222 (9)	0.0195 (8)	0.0156 (8)	−0.0012 (7)	0.0027 (6)	−0.0030 (6)
C4	0.0127 (7)	0.0138 (8)	0.0169 (8)	0.0004 (6)	−0.0007 (6)	−0.0020 (6)
C5	0.0167 (8)	0.0168 (8)	0.0210 (8)	−0.0043 (7)	0.0009 (6)	−0.0003 (6)
C6	0.0224 (9)	0.0202 (9)	0.0266 (9)	−0.0051 (7)	−0.0034 (7)	0.0044 (7)
C7	0.0230 (9)	0.0162 (8)	0.0348 (10)	−0.0033 (7)	0.0087 (8)	−0.0008 (7)
C8	0.0174 (9)	0.0198 (9)	0.0320 (10)	−0.0012 (7)	0.0055 (7)	−0.0023 (7)
C9	0.0168 (8)	0.0207 (8)	0.0146 (8)	−0.0062 (7)	0.0003 (6)	−0.0039 (6)
C10	0.0217 (9)	0.0158 (8)	0.0245 (9)	−0.0048 (7)	0.0021 (7)	−0.0055 (7)
C11	0.0193 (8)	0.0175 (8)	0.0259 (9)	−0.0031 (7)	0.0036 (7)	−0.0083 (7)
C12	0.0181 (8)	0.0198 (8)	0.0153 (8)	−0.0055 (7)	−0.0024 (6)	−0.0015 (6)
C13	0.0198 (9)	0.0213 (9)	0.0178 (8)	−0.0049 (7)	0.0006 (6)	0.0003 (7)
C14	0.0171 (8)	0.0241 (9)	0.0146 (8)	−0.0054 (7)	0.0000 (6)	−0.0003 (6)
C15	0.0238 (9)	0.0215 (9)	0.0283 (9)	−0.0043 (7)	0.0040 (7)	−0.0039 (7)
C16	0.0206 (9)	0.0304 (10)	0.0290 (10)	−0.0037 (8)	0.0076 (7)	−0.0062 (8)
C17	0.0255 (9)	0.0246 (9)	0.0260 (9)	−0.0096 (8)	0.0052 (7)	−0.0056 (7)
C18	0.0216 (9)	0.0248 (9)	0.0229 (9)	−0.0054 (7)	0.0045 (7)	−0.0067 (7)

Geometric parameters (Å, º) top

Cd—S1	2.6379 (10)	C4—H4B	0.9900
Cd—S2	2.6626 (10)	C5—C6	1.527 (2)
Cd—N2	2.5403 (17)	C5—H5A	0.9900
Cd—S1ⁱ	2.6379 (10)	C5—H5B	0.9900
Cd—S2ⁱ	2.6626 (10)	C6—H6A	0.9800
Cd—N2ⁱ	2.5403 (17)	C6—H6B	0.9800
S1—C1	1.7369 (17)	C6—H6C	0.9800
S2—C1	1.7286 (18)	C7—C8	1.385 (2)
O1—C3	1.421 (2)	C7—H7	0.9500
O1—H1o	0.835 (10)	C8—C9	1.395 (2)
N1—C1	1.339 (2)	C8—H8	0.9500
N1—C2	1.475 (2)	C9—C10	1.390 (2)
N1—C4	1.479 (2)	C9—C12	1.471 (2)
N2—C11	1.336 (2)	C10—C11	1.386 (2)
N2—C7	1.347 (2)	C10—H10	0.9500
N3—C12	1.280 (2)	C11—H11	0.9500
N3—N4	1.418 (2)	C12—H12	0.9500
N4—C13	1.279 (2)	C13—C14	1.475 (2)
N5—C16	1.333 (3)	C13—H13	0.9500
N5—C17	1.344 (2)	C14—C15	1.391 (2)
C2—C3	1.516 (2)	C14—C18	1.393 (3)
C2—H2A	0.9900	C15—C16	1.388 (3)
C2—H2B	0.9900	C15—H15	0.9500
C3—H3A	0.9900	C16—H16	0.9500
C3—H3B	0.9900	C17—C18	1.385 (2)
C4—C5	1.521 (2)	C17—H17	0.9500
C4—H4A	0.9900	C18—H18	0.9500

N2ⁱ—Cd—N2	180	C4—C5—C6	110.58 (14)
N2ⁱ—Cd—S1	89.42 (4)	C4—C5—H5A	109.5
N2—Cd—S1	90.58 (4)	C6—C5—H5A	109.5
N2ⁱ—Cd—S1ⁱ	90.58 (4)	C4—C5—H5B	109.5
N2—Cd—S1ⁱ	89.42 (4)	C6—C5—H5B	109.5
S1—Cd—S1ⁱ	180	H5A—C5—H5B	108.1
N2ⁱ—Cd—S2	87.62 (4)	C5—C6—H6A	109.5
N2—Cd—S2	92.38 (4)	C5—C6—H6B	109.5
S1—Cd—S2	68.83 (3)	H6A—C6—H6B	109.5
S1ⁱ—Cd—S2	111.17 (3)	C5—C6—H6C	109.5
N2ⁱ—Cd—S2ⁱ	92.38 (4)	H6A—C6—H6C	109.5
N2—Cd—S2ⁱ	87.62 (4)	H6B—C6—H6C	109.5
S1—Cd—S2ⁱ	111.17 (3)	N2—C7—C8	123.52 (17)
S1ⁱ—Cd—S2ⁱ	68.83 (3)	N2—C7—H7	118.2
S2—Cd—S2ⁱ	180	C8—C7—H7	118.2
C1—S1—Cd	86.05 (6)	C7—C8—C9	119.02 (16)
C1—S2—Cd	85.43 (6)	C7—C8—H8	120.5
C3—O1—H1o	109.5 (16)	C9—C8—H8	120.5
C1—N1—C2	121.74 (13)	C10—C9—C8	117.67 (15)
C1—N1—C4	121.96 (13)	C10—C9—C12	118.88 (15)
C2—N1—C4	116.29 (13)	C8—C9—C12	123.44 (16)
C11—N2—C7	116.95 (15)	C11—C10—C9	119.30 (16)
C11—N2—Cd	119.88 (11)	C11—C10—H10	120.3
C7—N2—Cd	123.16 (11)	C9—C10—H10	120.3
C12—N3—N4	110.47 (14)	N2—C11—C10	123.54 (16)
C13—N4—N3	111.93 (14)	N2—C11—H11	118.2
C16—N5—C17	116.98 (16)	C10—C11—H11	118.2
N1—C1—S2	120.59 (12)	N3—C12—C9	121.48 (16)
N1—C1—S1	119.77 (12)	N3—C12—H12	119.3
S2—C1—S1	119.64 (10)	C9—C12—H12	119.3
N1—C2—C3	113.01 (13)	N4—C13—C14	119.59 (16)
N1—C2—H2A	109.0	N4—C13—H13	120.2
C3—C2—H2A	109.0	C14—C13—H13	120.2
N1—C2—H2B	109.0	C15—C14—C18	117.63 (16)
C3—C2—H2B	109.0	C15—C14—C13	120.38 (16)
H2A—C2—H2B	107.8	C18—C14—C13	121.99 (16)
O1—C3—C2	110.27 (14)	C16—C15—C14	118.89 (17)
O1—C3—H3A	109.6	C16—C15—H15	120.6
C2—C3—H3A	109.6	C14—C15—H15	120.6
O1—C3—H3B	109.6	N5—C16—C15	123.90 (17)
C2—C3—H3B	109.6	N5—C16—H16	118.0
H3A—C3—H3B	108.1	C15—C16—H16	118.0
N1—C4—C5	113.22 (13)	N5—C17—C18	123.21 (17)
N1—C4—H4A	108.9	N5—C17—H17	118.4
C5—C4—H4A	108.9	C18—C17—H17	118.4
N1—C4—H4B	108.9	C17—C18—C14	119.38 (17)
C5—C4—H4B	108.9	C17—C18—H18	120.3
H4A—C4—H4B	107.7	C14—C18—H18	120.3

N2ⁱ—Cd—S1—C1	−86.27 (7)	C4—N1—C2—C3	−87.99 (17)
N2—Cd—S1—C1	93.73 (7)	N1—C2—C3—O1	70.19 (17)
S1ⁱ—Cd—S1—C1	95 (100)	C1—N1—C4—C5	90.95 (18)
S2—Cd—S1—C1	1.40 (5)	C2—N1—C4—C5	−89.78 (16)
S2ⁱ—Cd—S1—C1	−178.60 (5)	N1—C4—C5—C6	175.96 (13)
N2ⁱ—Cd—S2—C1	88.89 (7)	C11—N2—C7—C8	0.3 (3)
N2—Cd—S2—C1	−91.11 (7)	Cd—N2—C7—C8	179.02 (14)
S1—Cd—S2—C1	−1.41 (5)	N2—C7—C8—C9	−0.1 (3)
S1ⁱ—Cd—S2—C1	178.59 (5)	C7—C8—C9—C10	−0.3 (3)
S2ⁱ—Cd—S2—C1	−29 (100)	C7—C8—C9—C12	−179.20 (17)
N2ⁱ—Cd—N2—C11	−146 (100)	C8—C9—C10—C11	0.5 (2)
S1—Cd—N2—C11	−10.78 (13)	C12—C9—C10—C11	179.47 (15)
S1ⁱ—Cd—N2—C11	169.22 (13)	C7—N2—C11—C10	−0.1 (3)
S2—Cd—N2—C11	58.06 (13)	Cd—N2—C11—C10	−178.83 (13)
S2ⁱ—Cd—N2—C11	−121.94 (13)	C9—C10—C11—N2	−0.3 (3)
N2ⁱ—Cd—N2—C7	35 (100)	N4—N3—C12—C9	176.90 (14)
S1—Cd—N2—C7	170.58 (14)	C10—C9—C12—N3	173.70 (15)
S1ⁱ—Cd—N2—C7	−9.42 (14)	C8—C9—C12—N3	−7.4 (3)
S2—Cd—N2—C7	−120.58 (14)	N3—N4—C13—C14	179.61 (14)
S2ⁱ—Cd—N2—C7	59.42 (14)	N4—C13—C14—C15	169.03 (16)
C12—N3—N4—C13	−177.28 (14)	N4—C13—C14—C18	−10.7 (3)
C2—N1—C1—S2	−2.1 (2)	C18—C14—C15—C16	−1.1 (3)
C4—N1—C1—S2	177.14 (10)	C13—C14—C15—C16	179.14 (16)
C2—N1—C1—S1	177.52 (10)	C17—N5—C16—C15	0.6 (3)
C4—N1—C1—S1	−3.2 (2)	C14—C15—C16—N5	0.4 (3)
Cd—S2—C1—N1	−178.09 (12)	C16—N5—C17—C18	−0.8 (3)
Cd—S2—C1—S1	2.29 (8)	N5—C17—C18—C14	0.1 (3)
Cd—S1—C1—N1	178.07 (12)	C15—C14—C18—C17	0.9 (3)
Cd—S1—C1—S2	−2.31 (8)	C13—C14—C18—C17	−179.34 (16)
C1—N1—C2—C3	91.28 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N5ⁱⁱ	0.84 (2)	1.98 (2)	2.810 (2)	176 (2)
C10—H10···O1ⁱⁱⁱ	0.95	2.55	3.480 (3)	168
C3—H3a···N4^iv	0.99	2.61	3.369 (3)	134

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

Experimental details

Crystal data
Chemical formula	[Cd(C₆H₁₂NOS₂)₂(C₁₂H₁₀N₄)₂]
M_r	889.45
Crystal system, space group	Triclinic, P1
Temperature (K)	98
a, b, c (Å)	8.532 (3), 10.951 (4), 11.184 (5)
α, β, γ (°)	79.59 (3), 88.06 (3), 78.23 (2)
V (Å³)	1006.2 (7)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.25 × 0.16 × 0.04

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 CCD diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.719, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	10677, 4150, 4009
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.062, 1.08
No. of reflections	4150
No. of parameters	245
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.40

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), PATTY in DIRDIF (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Cd—S1	2.6379 (10)	Cd—N2	2.5403 (17)
Cd—S2	2.6626 (10)

S1—Cd—S2	68.83 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N5ⁱ	0.835 (19)	1.977 (19)	2.810 (2)	176 (2)
C10—H10···O1ⁱⁱ	0.95	2.55	3.480 (3)	168
C3—H3a···N4ⁱⁱⁱ	0.99	2.61	3.369 (3)	134

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

References

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