cis-Bis(4-methyl-piperazine-1-carbo-dithio-ato-κS,S')bis-(pyridine-κN)cadmium.

In the title complex, [Cd(C(6)H(11)N(2)S(2))(2)(C(5)H(5)N)(2)], the Cd(II) ion is hexa-coordinated by two N atoms from two pyridine ligands and by four S atoms from two dithio-carbamate ligands in a distorted octa-hedral geometry. The Cd(II) ion lies on a twofold axis. The piperazine ring is in chair conformation and its least-squares plane makes a dihedral angle of 81.4 (1)° with that of the pyridine ring.

Related literature

For background to and applications of dithio­carbamates, see: Bessergenev et al. (1997 ▶); Havel (1975 ▶); Valarmathi et al. (2011 ▶); Pickett & O’Brien (2001 ▶). For related structures, see: Ivanov et al. (2006 ▶); Onwudiwe & Ajibade (2010 ▶); Yin et al. (2004 ▶).

Experimental

Crystal data

[Cd(C6n class="Species">H11N2S2)2(C5H5N)2]

M = 621.18

Monoclinic,

a = 17.7065 (7) Å

b = 8.7806 (6) Å

c = 20.6171 (8) Å

β = 122.276 (5)°

V = 2710.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.14 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.645, T max = 1.000

24135 measured reflections

2383 independent reflections

2088 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.057

S = 1.07

2383 reflections

151 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis n class="Disease">RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054791/nc2258sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054791/nc2258Isup2.hkl

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

[Cd(C6H11N2S2)2(C5H5N)2]	F(000) = 1272
Mr = 621.18	Dx = 1.522 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 11642 reflections
a = 17.7065 (7) Å	θ = 3.5–29.1°
b = 8.7806 (6) Å	µ = 1.14 mm−1
c = 20.6171 (8) Å	T = 293 K
β = 122.276 (5)°	Block, white
V = 2710.1 (2) Å3	0.3 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2383 independent reflections
Radiation source: fine-focus sealed tube	2088 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 16.1049 pixels mm-1	θmax = 25.0°, θmin = 3.8°
ω scans	h = −20→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −10→10
Tmin = 0.645, Tmax = 1.000	l = −24→24
24135 measured reflections

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0157P)2 + 4.0129P] where P = (Fo2 + 2Fc2)/3
2383 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
Cd1	0.0000	0.14900 (3)	0.2500	0.04703 (10)
S1	0.08961 (5)	0.12653 (8)	0.17998 (4)	0.05259 (19)
S2	−0.07368 (5)	−0.05272 (9)	0.13462 (4)	0.0550 (2)
C1	0.01848 (16)	−0.0220 (3)	0.12909 (13)	0.0415 (6)
N2	0.03409 (14)	−0.1100 (3)	0.08483 (12)	0.0472 (5)
C3	−0.01499 (18)	−0.2496 (3)	0.04814 (16)	0.0552 (7)
H3A	−0.0316	−0.2518	−0.0049	0.066*
H3B	−0.0692	−0.2532	0.0490	0.066*
C4	0.04322 (18)	−0.3850 (3)	0.09059 (16)	0.0537 (7)
H4A	0.0569	−0.3849	0.1428	0.064*
H4B	0.0109	−0.4780	0.0660	0.064*
N5	0.12635 (14)	−0.3821 (3)	0.09173 (12)	0.0486 (5)
C6	0.17350 (18)	−0.2393 (3)	0.12557 (16)	0.0535 (7)
H6A	0.2272	−0.2361	0.1239	0.064*
H6B	0.1913	−0.2354	0.1789	0.064*
C7	0.11636 (19)	−0.1028 (3)	0.08401 (17)	0.0552 (7)
H7A	0.1487	−0.0101	0.1089	0.066*
H7B	0.1018	−0.1019	0.0315	0.066*
C8	0.1830 (2)	−0.5113 (4)	0.13378 (18)	0.0658 (8)
H8A	0.2363	−0.5078	0.1323	0.099*
H8B	0.1514	−0.6042	0.1107	0.099*
H8C	0.1988	−0.5070	0.1861	0.099*
N9	−0.09469 (14)	0.3546 (3)	0.16984 (11)	0.0476 (5)
C10	−0.13114 (18)	0.3577 (4)	0.09431 (15)	0.0561 (7)
H10	−0.1166	0.2808	0.0718	0.067*
C11	−0.1891 (2)	0.4693 (4)	0.04841 (17)	0.0701 (9)
H11	−0.2141	0.4665	−0.0043	0.084*
C12	−0.2098 (2)	0.5841 (4)	0.0804 (2)	0.0707 (9)
H12	−0.2492	0.6608	0.0501	0.085*
C13	−0.1715 (2)	0.5845 (4)	0.1582 (2)	0.0702 (9)
H13	−0.1833	0.6625	0.1821	0.084*
C14	−0.1153 (2)	0.4675 (4)	0.20016 (17)	0.0625 (8)
H14	−0.0902	0.4674	0.2529	0.075*

	U11	U22	U33	U12	U13	U23
Cd1	0.05092 (17)	0.05401 (19)	0.03837 (15)	0.000	0.02532 (13)	0.000
S1	0.0537 (4)	0.0546 (4)	0.0574 (4)	−0.0160 (3)	0.0350 (4)	−0.0129 (3)
S2	0.0477 (4)	0.0652 (5)	0.0606 (4)	−0.0153 (3)	0.0346 (4)	−0.0175 (4)
C1	0.0434 (14)	0.0443 (15)	0.0351 (13)	0.0004 (12)	0.0198 (11)	0.0044 (11)
N2	0.0480 (12)	0.0535 (14)	0.0487 (12)	−0.0072 (10)	0.0317 (11)	−0.0095 (10)
C3	0.0494 (16)	0.066 (2)	0.0482 (16)	−0.0072 (14)	0.0247 (14)	−0.0184 (14)
C4	0.0593 (17)	0.0576 (18)	0.0497 (16)	−0.0190 (14)	0.0330 (14)	−0.0141 (13)
N5	0.0534 (13)	0.0503 (14)	0.0459 (12)	−0.0031 (11)	0.0291 (11)	−0.0021 (10)
C6	0.0502 (16)	0.0602 (18)	0.0599 (17)	−0.0077 (14)	0.0360 (14)	−0.0033 (15)
C7	0.0668 (18)	0.0536 (17)	0.0679 (19)	−0.0057 (14)	0.0511 (16)	−0.0017 (14)
C8	0.0697 (19)	0.060 (2)	0.0642 (19)	0.0003 (16)	0.0330 (16)	0.0036 (16)
N9	0.0469 (12)	0.0577 (14)	0.0362 (11)	0.0016 (11)	0.0208 (10)	−0.0025 (11)
C10	0.0576 (17)	0.072 (2)	0.0430 (15)	−0.0001 (16)	0.0295 (14)	−0.0007 (15)
C11	0.065 (2)	0.096 (3)	0.0455 (17)	0.0059 (19)	0.0269 (16)	0.0226 (18)
C12	0.0588 (19)	0.072 (2)	0.081 (2)	0.0091 (17)	0.0365 (18)	0.034 (2)
C13	0.078 (2)	0.0545 (19)	0.080 (2)	0.0082 (17)	0.0436 (19)	0.0018 (17)
C14	0.071 (2)	0.063 (2)	0.0449 (16)	0.0074 (16)	0.0251 (15)	−0.0054 (15)

Cd1—N9i	2.417 (2)	C6—C7	1.506 (4)
Cd1—N9	2.417 (2)	C6—H6A	0.9700
Cd1—S1i	2.6621 (7)	C6—H6B	0.9700
Cd1—S1	2.6621 (7)	C7—H7A	0.9700
Cd1—S2	2.6803 (7)	C7—H7B	0.9700
Cd1—S2i	2.6803 (7)	C8—H8A	0.9600
S1—C1	1.725 (3)	C8—H8B	0.9600
S2—C1	1.717 (2)	C8—H8C	0.9600
C1—N2	1.333 (3)	N9—C14	1.323 (3)
N2—C3	1.459 (3)	N9—C10	1.330 (3)
N2—C7	1.467 (3)	C10—C11	1.368 (4)
C3—C4	1.510 (4)	C10—H10	0.9300
C3—H3A	0.9700	C11—C12	1.359 (5)
C3—H3B	0.9700	C11—H11	0.9300
C4—N5	1.460 (3)	C12—C13	1.368 (4)
C4—H4A	0.9700	C12—H12	0.9300
C4—H4B	0.9700	C13—C14	1.369 (4)
N5—C8	1.455 (4)	C13—H13	0.9300
N5—C6	1.460 (3)	C14—H14	0.9300
N9i—Cd1—N9	83.36 (10)	C4—N5—C6	109.7 (2)
N9i—Cd1—S1i	94.66 (5)	N5—C6—C7	111.9 (2)
N9—Cd1—S1i	91.69 (5)	N5—C6—H6A	109.2
N9i—Cd1—S1	91.69 (5)	C7—C6—H6A	109.2
N9—Cd1—S1	94.66 (5)	N5—C6—H6B	109.2
S1i—Cd1—S1	171.50 (3)	C7—C6—H6B	109.2
N9i—Cd1—S2	158.69 (5)	H6A—C6—H6B	107.9
N9—Cd1—S2	93.18 (5)	N2—C7—C6	109.2 (2)
S1i—Cd1—S2	106.48 (2)	N2—C7—H7A	109.8
S1—Cd1—S2	67.56 (2)	C6—C7—H7A	109.8
N9i—Cd1—S2i	93.18 (5)	N2—C7—H7B	109.8
N9—Cd1—S2i	158.69 (5)	C6—C7—H7B	109.8
S1i—Cd1—S2i	67.56 (2)	H7A—C7—H7B	108.3
S1—Cd1—S2i	106.48 (2)	N5—C8—H8A	109.5
S2—Cd1—S2i	97.27 (4)	N5—C8—H8B	109.5
C1—S1—Cd1	86.15 (8)	H8A—C8—H8B	109.5
C1—S2—Cd1	85.73 (9)	N5—C8—H8C	109.5
N2—C1—S2	120.42 (19)	H8A—C8—H8C	109.5
N2—C1—S1	120.25 (18)	H8B—C8—H8C	109.5
S2—C1—S1	119.31 (15)	C14—N9—C10	117.0 (2)
C1—N2—C3	123.9 (2)	C14—N9—Cd1	120.15 (18)
C1—N2—C7	123.6 (2)	C10—N9—Cd1	122.80 (19)
C3—N2—C7	110.5 (2)	N9—C10—C11	122.7 (3)
N2—C3—C4	109.1 (2)	N9—C10—H10	118.6
N2—C3—H3A	109.9	C11—C10—H10	118.6
C4—C3—H3A	109.9	C12—C11—C10	119.5 (3)
N2—C3—H3B	109.9	C12—C11—H11	120.2
C4—C3—H3B	109.9	C10—C11—H11	120.2
H3A—C3—H3B	108.3	C11—C12—C13	118.5 (3)
N5—C4—C3	111.5 (2)	C11—C12—H12	120.7
N5—C4—H4A	109.3	C13—C12—H12	120.7
C3—C4—H4A	109.3	C12—C13—C14	118.5 (3)
N5—C4—H4B	109.3	C12—C13—H13	120.8
C3—C4—H4B	109.3	C14—C13—H13	120.8
H4A—C4—H4B	108.0	N9—C14—C13	123.7 (3)
C8—N5—C4	111.4 (2)	N9—C14—H14	118.2
C8—N5—C6	110.4 (2)	C13—C14—H14	118.2
N9i—Cd1—S1—C1	178.45 (10)	C8—N5—C6—C7	−179.3 (2)
N9—Cd1—S1—C1	−98.07 (10)	C4—N5—C6—C7	−56.2 (3)
S1i—Cd1—S1—C1	40.12 (8)	C1—N2—C7—C6	105.6 (3)
S2—Cd1—S1—C1	−6.55 (8)	C3—N2—C7—C6	−59.0 (3)
S2i—Cd1—S1—C1	84.63 (9)	N5—C6—C7—N2	57.5 (3)
N9i—Cd1—S2—C1	20.45 (18)	N9i—Cd1—N9—C14	−49.4 (2)
N9—Cd1—S2—C1	100.31 (10)	S1i—Cd1—N9—C14	45.1 (2)
S1i—Cd1—S2—C1	−166.98 (8)	S1—Cd1—N9—C14	−140.6 (2)
S1—Cd1—S2—C1	6.58 (8)	S2—Cd1—N9—C14	151.7 (2)
S2i—Cd1—S2—C1	−98.30 (9)	S2i—Cd1—N9—C14	32.3 (3)
Cd1—S2—C1—N2	170.5 (2)	N9i—Cd1—N9—C10	133.4 (2)
Cd1—S2—C1—S1	−10.81 (13)	S1i—Cd1—N9—C10	−132.1 (2)
Cd1—S1—C1—N2	−170.4 (2)	S1—Cd1—N9—C10	42.2 (2)
Cd1—S1—C1—S2	10.87 (14)	S2—Cd1—N9—C10	−25.5 (2)
S2—C1—N2—C3	−9.9 (3)	S2i—Cd1—N9—C10	−144.91 (17)
S1—C1—N2—C3	171.4 (2)	C14—N9—C10—C11	−1.4 (4)
S2—C1—N2—C7	−172.5 (2)	Cd1—N9—C10—C11	175.9 (2)
S1—C1—N2—C7	8.8 (3)	N9—C10—C11—C12	1.2 (5)
C1—N2—C3—C4	−105.1 (3)	C10—C11—C12—C13	0.2 (5)
C7—N2—C3—C4	59.5 (3)	C11—C12—C13—C14	−1.3 (5)
N2—C3—C4—N5	−58.5 (3)	C10—N9—C14—C13	0.3 (4)
C3—C4—N5—C8	179.0 (2)	Cd1—N9—C14—C13	−177.1 (2)
C3—C4—N5—C6	56.5 (3)	C12—C13—C14—N9	1.1 (5)