(2,2′-Bipyrid­yl)bis­[N-(2-hydroxy­ethyl)-N-n-propyl­dithio­carbamato-κ2S,S′]cadmium(II) acetonitrile solvate

Song, J.C.; Tiekink, E.R.T.

doi:10.1107/S1600536809049666

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1669-m1670

doi:10.1107/S1600536809049666

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(2,2′-Bipyridyl)bis[N-(2-hydroxyethyl)-N-n-propyldithiocarbamato-κ²S,S′]cadmium(II) acetonitrile solvate

Juyoung C. Song ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 19 November 2009; accepted 19 November 2009; online 25 November 2009)

The title complex, [Cd(C₆H₁₂NOS₂)₂(C₁₀H₈N₂)]·CH₃CN, features a distorted octahedral N₂S₄ geometry for the Cd^II centre defined by a pair of asymmetrically chelating dithiocarbamate ligands as well as a 2,2′-bipyridine ligand. Supramolecular chains along [001] are formed in the crystal structure, mediated by O—H⋯S hydrogen bonds; the acetonitrile solvent molecules are associated with the chains via O—H⋯N hydrogen bonds.

Related literature

For background to supramolecular polymers of zinc-triad 1,1-dithiolates, see: Tiekink (2003 ); Lai et al. (2002 ); Chen et al. (2006 ); Benson et al. (2007 ). For the synthesis, see: Lai & Tiekink (2004 ).

Experimental

Crystal data

[Cd(C₆H₁₂NOS₂)₂(C₁₀H₈N₂)]·C₂H₃N
M_r = 666.21
Monoclinic, P 2₁ /c
a = 7.3277 (7) Å
b = 23.822 (2) Å
c = 17.1159 (18) Å
β = 99.786 (1)°
V = 2944.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 98 K
0.36 × 0.22 × 0.11 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.828, T_max = 1
18201 measured reflections
6043 independent reflections
5711 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.080
S = 1.09
6043 reflections
331 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd—N3	2.361 (2)
Cd—N4	2.406 (2)
Cd—S1	2.5872 (7)
Cd—S3	2.6539 (7)
Cd—S4	2.6704 (7)
Cd—S2	2.7816 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N5	0.84	2.06	2.898 (3)	174
O2—H2o⋯S2ⁱ	0.84	2.55	3.388 (2)	175
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: PATTY in DIRDIF92 (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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049666/hb5240sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049666/hb5240Isup2.hkl

checkCIF report

Comment top

Crystal engineering studies on the zinc-triad 1,1-dithiolates have generated 1-D, 2-D and 3-D architectures (Lai et al., 2002; Tiekink, 2003; Chen et al., 2006), in particular with dithiocarbamate ligands functionalized with hydrogen-bonding capacity (Benson et al., 2007). As a continuation of studies in this field, the structure of the title compound, (I), was investigated.

The molecular structure of (I) features a hexa-coordinated Cd^II centre defined by two asymmetrically chelating dithiocarbamate ligands (Cd–S1, S2 = 2.5872 (7) and 2.7816 (7) Å, and Cd–S3, S4 = 2.6539 (7) and 2.6704 (7) Å) and a chelating 2,2'-bipyridyl ligand (Cd–N3, N4 = 2.361 (2), 2.406 (2) Å). The resulting N₂S₄ donor set defines a distorted octahedral geometry.

The crystal packing is dominated by O–H···O and O–H···N hydrogen bonds, Table 1. The latter involve the O1-hydroxyl group and the nitrile-N5 atom of the solvent acetonitrile molecule. The O2-hydroxyl group forms hydrogen bonds with the dithiocarbamate-S2 atom to generate a supramolecular chain along [0 0 1], Table 1 and Fig. 2.

Related literature top

For background to supramolecular polymers of zinc-triad 1,1-dithiolates, see: Tiekink (2003); Lai et al. (2002); Chen et al. (2006); Benson et al. (2007). For the synthesis, see: Lai & Tiekink (2004).

Experimental top

Compound (I) was prepared following the standard literature procedure from the reaction of Cd[S₂CN(CH₂CH₂OH)(n-Pr)]₂ and 2,2'-bipyridyl (Lai & Tiekink, 2004). Colourless crystals were obtained from the slow evaporation of an acetonitrile solution of (I). IR (KBr, cm^-1): 1471 (m) ν(C=N); 1183 (s) ν(C—S).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: PATTY in DIRDIF92 (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, 2009).

Figures top

	Fig. 1. Molecular structure of (I) showing displacement ellipsoids at the 50% probability level. The O–H···N hydrogen bond is shown as a dashed line.
	Fig. 2. Supramolecular chain in (I) mediated by O–H···S (green dashed lines) hydrogen bonds. The solvent acetonitrile molecules are connected by O–H···N hydrogen bonds (orange dashed lines). Hydrogen atoms not involved in the hydrogen bonding are omitted for reasons of clarity. Colour code: Cd, orange; S, yellow; O, red; N, blue; C, grey; and H, green.

(2,2'-Bipyridyl)bis[N-(2-hydroxyethyl)-N-n- propyldithiocarbamato-κ²S,S']cadmium(II) acetonitrile solvate top

Crystal data top

[Cd(C₆H₁₂NOS₂)₂(C₁₀H₈N₂)]·C₂H₃N	F(000) = 1368
M_r = 666.21	D_x = 1.503 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 18141 reflections
a = 7.3277 (7) Å	θ = 2.1–40.6°
b = 23.822 (2) Å	µ = 1.06 mm⁻¹
c = 17.1159 (18) Å	T = 98 K
β = 99.786 (1)°	Block, colourless
V = 2944.2 (5) Å³	0.36 × 0.22 × 0.11 mm
Z = 4

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	6043 independent reflections
Radiation source: fine-focus sealed tube	5711 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 26.5°, θ_min = 2.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.828, T_max = 1	k = −25→29
18201 measured reflections	l = −21→21

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0396P)² + 3.165P] where P = (F_o² + 2F_c²)/3
6043 reflections	(Δ/σ)_max = 0.004
331 parameters	Δρ_max = 0.70 e Å⁻³
2 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Cd(C₆H₁₂NOS₂)₂(C₁₀H₈N₂)]·C₂H₃N	V = 2944.2 (5) Å³
M_r = 666.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3277 (7) Å	µ = 1.06 mm⁻¹
b = 23.822 (2) Å	T = 98 K
c = 17.1159 (18) Å	0.36 × 0.22 × 0.11 mm
β = 99.786 (1)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	6043 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5711 reflections with I > 2σ(I)
T_min = 0.828, T_max = 1	R_int = 0.027
18201 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	2 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.09	Δρ_max = 0.70 e Å⁻³
6043 reflections	Δρ_min = −0.69 e Å⁻³
331 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
Cd	0.22264 (2)	0.757722 (7)	0.046853 (9)	0.01758 (7)
S1	0.17585 (8)	0.85953 (3)	0.09227 (3)	0.01984 (13)
S2	0.54757 (9)	0.82033 (3)	0.06550 (4)	0.02253 (13)
S3	0.35255 (9)	0.69177 (3)	0.16861 (4)	0.02338 (14)
S4	−0.04308 (9)	0.69484 (3)	0.09167 (3)	0.02234 (13)
O1	0.7384 (3)	0.95516 (8)	0.26074 (11)	0.0274 (4)
H1O	0.8084	0.9465	0.3031	0.041*
O2	0.4126 (3)	0.60342 (9)	0.39861 (11)	0.0356 (5)
H2O	0.4471	0.6205	0.4415	0.053*
N1	0.4822 (3)	0.92222 (9)	0.11936 (11)	0.0184 (4)
N2	0.0887 (3)	0.62810 (9)	0.21271 (12)	0.0215 (4)
N3	0.3447 (3)	0.70592 (9)	−0.04998 (12)	0.0205 (4)
N4	0.0208 (3)	0.76057 (8)	−0.07961 (12)	0.0177 (4)
N5	0.9711 (4)	0.93255 (13)	0.41198 (16)	0.0471 (8)
C1	0.4102 (3)	0.87219 (10)	0.09512 (13)	0.0183 (5)
C2	0.6792 (3)	0.93562 (11)	0.12198 (14)	0.0212 (5)
H2A	0.6918	0.9762	0.1116	0.025*
H2B	0.7258	0.9146	0.0795	0.025*
C3	0.7967 (4)	0.92111 (12)	0.20105 (15)	0.0250 (5)
H3A	0.7818	0.8809	0.2132	0.030*
H3B	0.9290	0.9282	0.1991	0.030*
C4	0.3645 (3)	0.96886 (10)	0.13808 (13)	0.0195 (5)
H4A	0.4397	0.9948	0.1758	0.023*
H4B	0.2640	0.9538	0.1640	0.023*
C5	0.2802 (4)	1.00116 (11)	0.06364 (14)	0.0218 (5)
H5A	0.3806	1.0175	0.0388	0.026*
H5B	0.2086	0.9750	0.0251	0.026*
C6	0.1535 (4)	1.04789 (12)	0.08326 (16)	0.0263 (5)
H6A	0.1014	1.0680	0.0346	0.039*
H6B	0.2248	1.0741	0.1207	0.039*
H6C	0.0530	1.0317	0.1071	0.039*
C7	0.1289 (3)	0.66779 (11)	0.16308 (14)	0.0198 (5)
C8	0.2339 (4)	0.60092 (11)	0.27098 (14)	0.0227 (5)
H8A	0.3515	0.6003	0.2498	0.027*
H8B	0.1977	0.5616	0.2792	0.027*
C9	0.2634 (4)	0.63157 (12)	0.34969 (14)	0.0241 (5)
H9A	0.2952	0.6714	0.3424	0.029*
H9B	0.1500	0.6300	0.3739	0.029*
C10	−0.1000 (4)	0.60685 (11)	0.21058 (15)	0.0232 (5)
H10A	−0.1895	0.6373	0.1930	0.028*
H10B	−0.1155	0.5956	0.2648	0.028*
C11	−0.1435 (4)	0.55671 (12)	0.15499 (17)	0.0293 (6)
H11A	−0.1319	0.5680	0.1004	0.035*
H11B	−0.0530	0.5264	0.1717	0.035*
C12	−0.3363 (4)	0.53524 (15)	0.15584 (18)	0.0370 (7)
H12A	−0.3612	0.5032	0.1198	0.056*
H12B	−0.4261	0.5651	0.1386	0.056*
H12C	−0.3472	0.5235	0.2097	0.056*
C13	−0.1430 (3)	0.78695 (11)	−0.09045 (15)	0.0223 (5)
H13	−0.1766	0.8074	−0.0474	0.027*
C14	−0.2656 (4)	0.78577 (12)	−0.16151 (16)	0.0267 (6)
H14	−0.3805	0.8051	−0.1672	0.032*
C15	−0.2165 (4)	0.75569 (11)	−0.22421 (16)	0.0267 (6)
H15	−0.2978	0.7540	−0.2737	0.032*
C16	−0.0475 (4)	0.72821 (11)	−0.21382 (14)	0.0230 (5)
H16	−0.0107	0.7078	−0.2562	0.028*
C17	0.0676 (3)	0.73098 (10)	−0.14026 (14)	0.0179 (5)
C18	0.2499 (3)	0.70174 (10)	−0.12429 (14)	0.0193 (5)
C19	0.5105 (4)	0.68052 (12)	−0.03162 (16)	0.0274 (6)
H19	0.5775	0.6842	0.0207	0.033*
C20	0.5869 (4)	0.64932 (13)	−0.08592 (18)	0.0342 (6)
H20	0.7039	0.6316	−0.0714	0.041*
C21	0.4884 (4)	0.64455 (14)	−0.16209 (18)	0.0370 (7)
H21	0.5371	0.6231	−0.2006	0.044*
C22	0.3192 (4)	0.67099 (12)	−0.18219 (16)	0.0286 (6)
H22	0.2511	0.6683	−0.2345	0.034*
C23	1.0929 (4)	0.93296 (12)	0.46333 (17)	0.0319 (6)
C24	1.2471 (4)	0.93447 (15)	0.52810 (18)	0.0371 (7)
H24A	1.2018	0.9298	0.5784	0.056*
H24B	1.3111	0.9706	0.5280	0.056*
H24C	1.3333	0.9040	0.5219	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.01970 (10)	0.01859 (11)	0.01415 (10)	−0.00001 (6)	0.00205 (7)	−0.00045 (6)
S1	0.0183 (3)	0.0203 (3)	0.0206 (3)	0.0005 (2)	0.0026 (2)	−0.0025 (2)
S2	0.0221 (3)	0.0212 (3)	0.0254 (3)	0.0018 (2)	0.0072 (2)	−0.0035 (2)
S3	0.0212 (3)	0.0273 (3)	0.0199 (3)	−0.0013 (2)	−0.0016 (2)	0.0036 (2)
S4	0.0203 (3)	0.0270 (3)	0.0190 (3)	−0.0008 (2)	0.0012 (2)	0.0055 (2)
O1	0.0331 (11)	0.0274 (10)	0.0200 (9)	−0.0029 (8)	−0.0002 (7)	−0.0002 (7)
O2	0.0453 (12)	0.0394 (12)	0.0185 (9)	0.0197 (10)	−0.0048 (8)	−0.0023 (8)
N1	0.0191 (10)	0.0201 (11)	0.0160 (9)	0.0003 (8)	0.0036 (7)	−0.0002 (7)
N2	0.0249 (11)	0.0221 (11)	0.0173 (10)	0.0020 (8)	0.0032 (8)	0.0022 (8)
N3	0.0193 (10)	0.0221 (11)	0.0201 (10)	−0.0003 (8)	0.0033 (8)	−0.0016 (8)
N4	0.0209 (10)	0.0146 (10)	0.0177 (10)	0.0002 (8)	0.0035 (8)	0.0016 (7)
N5	0.0482 (17)	0.0513 (18)	0.0362 (14)	−0.0215 (14)	−0.0089 (12)	0.0155 (12)
C1	0.0203 (12)	0.0222 (13)	0.0122 (10)	0.0008 (9)	0.0025 (8)	0.0015 (8)
C2	0.0206 (12)	0.0237 (13)	0.0200 (11)	−0.0041 (10)	0.0058 (9)	0.0008 (9)
C3	0.0217 (13)	0.0285 (14)	0.0244 (13)	−0.0020 (10)	0.0030 (10)	0.0030 (10)
C4	0.0222 (12)	0.0192 (12)	0.0174 (11)	−0.0006 (9)	0.0042 (9)	−0.0033 (9)
C5	0.0239 (12)	0.0223 (13)	0.0190 (11)	0.0004 (10)	0.0034 (9)	−0.0016 (9)
C6	0.0260 (13)	0.0255 (14)	0.0287 (13)	0.0059 (10)	0.0082 (10)	0.0010 (10)
C7	0.0228 (12)	0.0204 (13)	0.0161 (11)	0.0012 (9)	0.0036 (9)	−0.0015 (9)
C8	0.0297 (13)	0.0191 (13)	0.0191 (11)	0.0073 (10)	0.0041 (10)	0.0011 (9)
C9	0.0288 (13)	0.0252 (14)	0.0184 (11)	0.0071 (10)	0.0042 (10)	0.0003 (9)
C10	0.0273 (13)	0.0235 (13)	0.0202 (11)	−0.0002 (10)	0.0077 (9)	0.0021 (9)
C11	0.0292 (14)	0.0274 (15)	0.0317 (14)	−0.0008 (11)	0.0064 (11)	−0.0028 (11)
C12	0.0318 (16)	0.0453 (19)	0.0338 (15)	−0.0093 (13)	0.0051 (12)	−0.0038 (13)
C13	0.0211 (12)	0.0233 (14)	0.0234 (12)	0.0031 (10)	0.0064 (9)	0.0023 (9)
C14	0.0233 (13)	0.0287 (15)	0.0273 (13)	0.0044 (10)	0.0013 (10)	0.0061 (10)
C15	0.0285 (14)	0.0263 (14)	0.0227 (13)	−0.0028 (10)	−0.0032 (11)	0.0037 (10)
C16	0.0286 (14)	0.0233 (13)	0.0166 (11)	−0.0040 (10)	0.0021 (10)	−0.0001 (9)
C17	0.0184 (12)	0.0192 (12)	0.0167 (11)	−0.0038 (9)	0.0047 (9)	0.0006 (9)
C18	0.0214 (12)	0.0192 (12)	0.0180 (11)	−0.0002 (9)	0.0052 (9)	−0.0007 (9)
C19	0.0198 (12)	0.0322 (15)	0.0293 (13)	0.0055 (11)	0.0017 (10)	0.0006 (11)
C20	0.0232 (14)	0.0375 (17)	0.0433 (17)	0.0086 (12)	0.0099 (12)	0.0007 (13)
C21	0.0359 (16)	0.0408 (18)	0.0381 (16)	0.0100 (13)	0.0171 (13)	−0.0078 (13)
C22	0.0315 (14)	0.0320 (16)	0.0238 (13)	0.0009 (11)	0.0087 (11)	−0.0069 (11)
C23	0.0374 (16)	0.0254 (15)	0.0330 (15)	−0.0055 (12)	0.0062 (12)	0.0069 (11)
C24	0.0341 (16)	0.0395 (18)	0.0361 (16)	0.0007 (13)	0.0013 (12)	0.0090 (13)

Geometric parameters (Å, º) top

Cd—N3	2.361 (2)	C6—H6B	0.9800
Cd—N4	2.406 (2)	C6—H6C	0.9800
Cd—S1	2.5872 (7)	C8—C9	1.515 (3)
Cd—S3	2.6539 (7)	C8—H8A	0.9900
Cd—S4	2.6704 (7)	C8—H8B	0.9900
Cd—S2	2.7816 (7)	C9—H9A	0.9900
S1—C1	1.736 (2)	C9—H9B	0.9900
S2—C1	1.723 (2)	C10—C11	1.527 (4)
S3—C7	1.723 (3)	C10—H10A	0.9900
S4—C7	1.724 (2)	C10—H10B	0.9900
O1—C3	1.426 (3)	C11—C12	1.505 (4)
O1—H1O	0.8400	C11—H11A	0.9900
O2—C9	1.427 (3)	C11—H11B	0.9900
O2—H2O	0.8400	C12—H12A	0.9800
N1—C1	1.340 (3)	C12—H12B	0.9800
N1—C2	1.472 (3)	C12—H12C	0.9800
N1—C4	1.475 (3)	C13—C14	1.384 (4)
N2—C7	1.337 (3)	C13—H13	0.9500
N2—C10	1.467 (3)	C14—C15	1.388 (4)
N2—C8	1.478 (3)	C14—H14	0.9500
N3—C19	1.345 (3)	C15—C16	1.385 (4)
N3—C18	1.345 (3)	C15—H15	0.9500
N4—C13	1.340 (3)	C16—C17	1.393 (3)
N4—C17	1.346 (3)	C16—H16	0.9500
N5—C23	1.141 (4)	C17—C18	1.490 (3)
C2—C3	1.515 (3)	C18—C22	1.395 (3)
C2—H2A	0.9900	C19—C20	1.381 (4)
C2—H2B	0.9900	C19—H19	0.9500
C3—H3A	0.9900	C20—C21	1.383 (4)
C3—H3B	0.9900	C20—H20	0.9500
C4—C5	1.526 (3)	C21—C22	1.381 (4)
C4—H4A	0.9900	C21—H21	0.9500
C4—H4B	0.9900	C22—H22	0.9500
C5—C6	1.523 (3)	C23—C24	1.443 (4)
C5—H5A	0.9900	C24—H24A	0.9800
C5—H5B	0.9900	C24—H24B	0.9800
C6—H6A	0.9800	C24—H24C	0.9800

N3—Cd—N4	68.37 (7)	S3—C7—S4	119.26 (14)
N3—Cd—S1	141.84 (5)	N2—C8—C9	111.5 (2)
N4—Cd—S1	98.70 (5)	N2—C8—H8A	109.3
N3—Cd—S3	96.53 (5)	C9—C8—H8A	109.3
N4—Cd—S3	143.78 (5)	N2—C8—H8B	109.3
S1—Cd—S3	111.54 (2)	C9—C8—H8B	109.3
N3—Cd—S4	106.87 (5)	H8A—C8—H8B	108.0
N4—Cd—S4	84.70 (5)	O2—C9—C8	105.9 (2)
S1—Cd—S4	107.40 (2)	O2—C9—H9A	110.5
S3—Cd—S4	67.92 (2)	C8—C9—H9A	110.6
N3—Cd—S2	86.66 (5)	O2—C9—H9B	110.5
N4—Cd—S2	118.12 (5)	C8—C9—H9B	110.5
S1—Cd—S2	67.51 (2)	H9A—C9—H9B	108.7
S3—Cd—S2	92.38 (2)	N2—C10—C11	112.4 (2)
S4—Cd—S2	156.855 (19)	N2—C10—H10A	109.1
C1—S1—Cd	89.45 (8)	C11—C10—H10A	109.1
C1—S2—Cd	83.49 (9)	N2—C10—H10B	109.1
C7—S3—Cd	86.69 (8)	C11—C10—H10B	109.1
C7—S4—Cd	86.13 (9)	H10A—C10—H10B	107.9
C3—O1—H1O	105.4	C12—C11—C10	110.9 (2)
C9—O2—H2O	111.9	C12—C11—H11A	109.5
C1—N1—C2	122.3 (2)	C10—C11—H11A	109.5
C1—N1—C4	121.6 (2)	C12—C11—H11B	109.5
C2—N1—C4	115.9 (2)	C10—C11—H11B	109.5
C7—N2—C10	122.5 (2)	H11A—C11—H11B	108.0
C7—N2—C8	121.8 (2)	C11—C12—H12A	109.5
C10—N2—C8	115.6 (2)	C11—C12—H12B	109.5
C19—N3—C18	119.2 (2)	H12A—C12—H12B	109.5
C19—N3—Cd	120.38 (17)	C11—C12—H12C	109.5
C18—N3—Cd	120.40 (16)	H12A—C12—H12C	109.5
C13—N4—C17	118.6 (2)	H12B—C12—H12C	109.5
C13—N4—Cd	122.48 (16)	N4—C13—C14	123.0 (2)
C17—N4—Cd	118.74 (16)	N4—C13—H13	118.5
N1—C1—S2	120.62 (18)	C14—C13—H13	118.5
N1—C1—S1	119.92 (18)	C13—C14—C15	118.4 (2)
S2—C1—S1	119.46 (14)	C13—C14—H14	120.8
N1—C2—C3	112.5 (2)	C15—C14—H14	120.8
N1—C2—H2A	109.1	C16—C15—C14	119.2 (2)
C3—C2—H2A	109.1	C16—C15—H15	120.4
N1—C2—H2B	109.1	C14—C15—H15	120.4
C3—C2—H2B	109.1	C15—C16—C17	119.0 (2)
H2A—C2—H2B	107.8	C15—C16—H16	120.5
O1—C3—C2	108.4 (2)	C17—C16—H16	120.5
O1—C3—H3A	110.0	N4—C17—C16	121.8 (2)
C2—C3—H3A	110.0	N4—C17—C18	116.2 (2)
O1—C3—H3B	110.0	C16—C17—C18	122.0 (2)
C2—C3—H3B	110.0	N3—C18—C22	121.2 (2)
H3A—C3—H3B	108.4	N3—C18—C17	116.2 (2)
N1—C4—C5	111.54 (19)	C22—C18—C17	122.6 (2)
N1—C4—H4A	109.3	N3—C19—C20	122.6 (3)
C5—C4—H4A	109.3	N3—C19—H19	118.7
N1—C4—H4B	109.3	C20—C19—H19	118.7
C5—C4—H4B	109.3	C19—C20—C21	118.2 (3)
H4A—C4—H4B	108.0	C19—C20—H20	120.9
C6—C5—C4	111.1 (2)	C21—C20—H20	120.9
C6—C5—H5A	109.4	C22—C21—C20	120.0 (3)
C4—C5—H5A	109.4	C22—C21—H21	120.0
C6—C5—H5B	109.4	C20—C21—H21	120.0
C4—C5—H5B	109.4	C21—C22—C18	118.8 (3)
H5A—C5—H5B	108.0	C21—C22—H22	120.6
C5—C6—H6A	109.5	C18—C22—H22	120.6
C5—C6—H6B	109.5	N5—C23—C24	179.1 (3)
H6A—C6—H6B	109.5	C23—C24—H24A	109.5
C5—C6—H6C	109.5	C23—C24—H24B	109.5
H6A—C6—H6C	109.5	H24A—C24—H24B	109.5
H6B—C6—H6C	109.5	C23—C24—H24C	109.5
N2—C7—S3	120.65 (19)	H24A—C24—H24C	109.5
N2—C7—S4	120.09 (19)	H24B—C24—H24C	109.5

N3—Cd—S1—C1	−52.88 (11)	Cd—S1—C1—S2	3.16 (13)
N4—Cd—S1—C1	−118.76 (9)	C1—N1—C2—C3	−90.2 (3)
S3—Cd—S1—C1	81.54 (8)	C4—N1—C2—C3	95.2 (3)
S4—Cd—S1—C1	154.10 (8)	N1—C2—C3—O1	−63.7 (3)
S2—Cd—S1—C1	−1.85 (7)	C1—N1—C4—C5	−83.9 (3)
N3—Cd—S2—C1	153.10 (9)	C2—N1—C4—C5	90.8 (2)
N4—Cd—S2—C1	89.84 (9)	N1—C4—C5—C6	177.9 (2)
S1—Cd—S2—C1	1.87 (8)	C10—N2—C7—S3	179.42 (18)
S3—Cd—S2—C1	−110.49 (8)	C8—N2—C7—S3	−3.5 (3)
S4—Cd—S2—C1	−79.80 (9)	C10—N2—C7—S4	−1.5 (3)
N3—Cd—S3—C7	−105.50 (10)	C8—N2—C7—S4	175.58 (18)
N4—Cd—S3—C7	−43.64 (12)	Cd—S3—C7—N2	178.9 (2)
S1—Cd—S3—C7	100.87 (8)	Cd—S3—C7—S4	−0.15 (14)
S4—Cd—S3—C7	0.09 (8)	Cd—S4—C7—N2	−178.9 (2)
S2—Cd—S3—C7	167.59 (8)	Cd—S4—C7—S3	0.15 (13)
N3—Cd—S4—C7	90.20 (10)	C7—N2—C8—C9	91.3 (3)
N4—Cd—S4—C7	155.69 (10)	C10—N2—C8—C9	−91.5 (3)
S1—Cd—S4—C7	−106.83 (8)	N2—C8—C9—O2	−176.7 (2)
S3—Cd—S4—C7	−0.09 (8)	C7—N2—C10—C11	89.8 (3)
S2—Cd—S4—C7	−33.49 (10)	C8—N2—C10—C11	−87.4 (3)
N4—Cd—N3—C19	178.4 (2)	N2—C10—C11—C12	178.6 (2)
S1—Cd—N3—C19	102.4 (2)	C17—N4—C13—C14	−0.8 (4)
S3—Cd—N3—C19	−35.7 (2)	Cd—N4—C13—C14	−175.62 (19)
S4—Cd—N3—C19	−104.5 (2)	N4—C13—C14—C15	0.2 (4)
S2—Cd—N3—C19	56.3 (2)	C13—C14—C15—C16	−0.2 (4)
N4—Cd—N3—C18	−1.17 (17)	C14—C15—C16—C17	0.8 (4)
S1—Cd—N3—C18	−77.2 (2)	C13—N4—C17—C16	1.4 (4)
S3—Cd—N3—C18	144.74 (18)	Cd—N4—C17—C16	176.40 (18)
S4—Cd—N3—C18	75.88 (18)	C13—N4—C17—C18	−179.0 (2)
S2—Cd—N3—C18	−123.25 (18)	Cd—N4—C17—C18	−4.0 (3)
N3—Cd—N4—C13	177.6 (2)	C15—C16—C17—N4	−1.4 (4)
S1—Cd—N4—C13	−39.79 (19)	C15—C16—C17—C18	179.0 (2)
S3—Cd—N4—C13	107.09 (19)	C19—N3—C18—C22	0.9 (4)
S4—Cd—N4—C13	67.05 (19)	Cd—N3—C18—C22	−179.6 (2)
S2—Cd—N4—C13	−108.88 (19)	C19—N3—C18—C17	−179.9 (2)
N3—Cd—N4—C17	2.78 (17)	Cd—N3—C18—C17	−0.3 (3)
S1—Cd—N4—C17	145.43 (16)	N4—C17—C18—N3	2.9 (3)
S3—Cd—N4—C17	−67.7 (2)	C16—C17—C18—N3	−177.5 (2)
S4—Cd—N4—C17	−107.73 (17)	N4—C17—C18—C22	−177.9 (2)
S2—Cd—N4—C17	76.34 (18)	C16—C17—C18—C22	1.7 (4)
C2—N1—C1—S2	0.1 (3)	C18—N3—C19—C20	−1.0 (4)
C4—N1—C1—S2	174.40 (16)	Cd—N3—C19—C20	179.4 (2)
C2—N1—C1—S1	−179.15 (17)	N3—C19—C20—C21	0.4 (5)
C4—N1—C1—S1	−4.8 (3)	C19—C20—C21—C22	0.5 (5)
Cd—S2—C1—N1	177.82 (19)	C20—C21—C22—C18	−0.7 (5)
Cd—S2—C1—S1	−2.96 (12)	N3—C18—C22—C21	0.0 (4)
Cd—S1—C1—N1	−177.61 (18)	C17—C18—C22—C21	−179.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N5	0.84	2.06	2.898 (3)	174
O2—H2o···S2ⁱ	0.84	2.55	3.388 (2)	175

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Cd(C₆H₁₂NOS₂)₂(C₁₀H₈N₂)]·C₂H₃N
M_r	666.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	98
a, b, c (Å)	7.3277 (7), 23.822 (2), 17.1159 (18)
β (°)	99.786 (1)
V (Å³)	2944.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.36 × 0.22 × 0.11

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.828, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	18201, 6043, 5711
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.080, 1.09
No. of reflections	6043
No. of parameters	331
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.69

Computer programs: CrystalClear (Rigaku/MSC, 2005), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Cd—N3	2.361 (2)	Cd—S3	2.6539 (7)
Cd—N4	2.406 (2)	Cd—S4	2.6704 (7)
Cd—S1	2.5872 (7)	Cd—S2	2.7816 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N5	0.84	2.06	2.898 (3)	174
O2—H2o···S2ⁱ	0.84	2.55	3.388 (2)	175

Symmetry code: (i) x, −y+3/2, z+1/2.

References

Benson, R. E., Ellis, C. A., Lewis, C. E. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 930–940. Web of Science CSD CrossRef CAS Google Scholar
Beurskens, P. T., Admiraal, G., Beurskens, G., Bosman, W. P., Garcia-Granda, S., Gould, R. O., Smits, J. M. M. & Smykalla, C. (1992). The DIRDIF Program System. Technical Report. Crystallography Laboratory, University of Nijmegen, The Netherlands. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chen, D., Lai, C. S. & Tiekink, E. R. T. (2006). CrystEngComm, 8, 51–58. Web of Science CSD CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Lai, C. S., Lim, Y. X., Yap, T. C. & Tiekink, E. R. T. (2002). CrystEngComm, 4, 596–600. Web of Science CSD CrossRef CAS Google Scholar
Lai, C. S. & Tiekink, E. R. T. (2004). CrystEngComm, 6, 593–605. Web of Science CSD CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tiekink, E. R. T. (2003). CrystEngComm, 5, 101–113. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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Volume 65| Part 12| December 2009| Pages m1669-m1670

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