Bis[N-(2-hy-droxy-eth-yl)-N-propyl-dithio-carbamato-κS,S']bis-(4-{[(pyridin-4-yl-methyl-idene)hydrazinyl-idene]meth-yl}pyridine-κN)cadmium.

The complete mol-ecule of the title compound, [Cd(C(6)H(12)NOS(2))(2)(C(12)H(10)N(4))(2)], is generated by crystallographic inversion symmetry. The distorted octa-hedral trans-N(2)S(4) donor set for the Cd(2+) ion is defined by two symmetrically S,S'-chelating dithio-carbamate anions and two pyridine N atoms derived from two monodentate 4-pyridine-aldazine (or 4-{[(pyridin-4-yl-methyl-idene)hydrazinyl-idene}meth-yl]pyridine) mol-ecules [dihedral angle between the aromatic rings = 17.33 (8)°]. In the crystal, mol-ecules are connected into a supra-molecular chain via O-H⋯N hydrogen bonds involving the 4-pyridine-aldazine 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 = 889.45

Triclinic,

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[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.062

S = 1.08

4150 reflections

245 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.40 e Å−3

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 ▶).

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

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

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

[Cd(C6H12NOS2)2(C12H10N4)2]	Z = 1
Mr = 889.45	F(000) = 458
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0288P)2 + 0.6008P] where P = (Fo2 + 2Fc2)/3
4150 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.40 e Å−3
1 restraint	Δρmin = −0.40 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···N4iv	0.99	2.61	3.369 (3)	134

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) ; (ii) ; (iii) .