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Acta Cryst. (2008). E64, m1176    [ doi:10.1107/S1600536808025889 ]

([mu]-2-Pyridinealdazine-[kappa]4N,N':N'',N''')bis[bis(N,N-di-n-propyldithiocarbamato-[kappa]2S,S')cadmium(II)]

P. Poplaukhin and E. R. T. Tiekink

Abstract top

The dinuclear centrosymmetric title compound, [Cd2(C7H14NS2)4(C12H10N4)], features a tetradentate 2-pyridinealdazine ligand that chelates two Cd centres. The coordination geometry for Cd is distorted octahedral based on a cis-N2S4 donor set. In the crystal structure, molecules are connected into a supramolecular chain aligned along the a direction via C-H...S and C-H...[pi] contacts, and by [pi]-[pi] contacts [centroid-to-centroid distance 3.5708 (15) Å]. The n-propyl groups are each disordered, one equally over two sites and the other with a site-occupancy factor of 0.618 (8) for the major component.

Comment top

Metal dithiocarbamates have recently been applied in crystal engineering studies (e.g. Tiekink, 2006; Benson et al., 2007). The title compound, {[(nPr)2NCS2]2Cd(2-C5H4N—C(H)═N—N═C(H)C5H4N-2)- Cd[S2CN(nPr)2]2} (I), features a centrosymmetric tetradentate 2-pyridinealdazine ligand coordinating to two Cd centres each of which is chelated by two dithiocarbamate ligands, Fig. 1. The molecule is centrosymmetric about the central N—N bond. The range of Cd—S bond distances is relatively narrow at 2.6124 (8) to 2.7165 (7) Å, but the Cd—N bond formed by the pyridine-N of 2.377 (2) Å is significantly shorter than the Cd—N bond distance of 2.6211 (19) Å formed with the azo-N atom. The coordination geometry is based on an octahedron within a cis-N2S4 donor set. The structure reported here for (I) resembles closely the dithiophosphate analogue (Lai & Tiekink, 2006). In the crystal structure, molecules are connected into a supramolecular chain, aligned along the a-direction and illustrated in Fig. 2, via C—H···S3 and π–π contacts. The latter occur between centrosymmetically related N3,C15—C19 rings with Cg···Cg = 3.5708 (15) Å. These are consolidated into the crystal structure via additional C—H···S4 contacts and C—H···π interactions, Table 1 and Fig. 3.

Related literature top

For background literature, see: Tiekink (2006); Benson et al. (2007). For a related structure, see: Lai & Tiekink (2006).

Experimental top

Compound (I) was prepared by standard methods (Benson et al., 2007) and red crystals were grown by the slow evaporation of a methanol–ethanol (1/1) solution of (I), m.p. 441-443 K. IR (cm-1): 1474 (s, C═N), 1171 (s, C—S). TGA: One broad step with onset = 625 K, midpoint = 662 K, and endset = 711 K which corresponds to decomposition leading to CdS (mass loss 79.4% cf. theoretical mass loss = 74.4%).

Refinement top

The H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl-C). The N1-bound n-propyl groups were each found to be disordered. The C6—C7 residue was disordered over two positions, each with 50% site occupancy factors (from anisotropic refinement). The C3 atom of the C2—C4 residue was disordered over two positions with the major component having a site occupancy factor = 0.618 (8) (from anisotropic refinement).

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: SIR92 (Altomare et al., 1994); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing the crystallographic numbering scheme. Displacement ellipsoids are shown at the 50% probability level. Unlabelled atoms are related by the symmetry operation i: -x, 1 - y, 1 - z. The minor components of the disordered n-propyl groups omitted for clarity.
[Figure 2] Fig. 2. View of a supramolecular chain in (I) highlighting the overlap of the aromatic rings to allow the formation of the π–π interactions. The C—H···S3 interactions are shown as orange dashed lines. Colour code: Cd (orange), S (yellow), O (red), N (blue), C (grey) & H (green).
[Figure 3] Fig. 3. View in projection of the crystal packing in (I). Colour code as for Fig. 2.
(µ-2-Pyridinealdazine- κ4N,N':N'',N''')bis[bis(N,N-di-n- propyldithiocarbamato-κ2S,S')cadmium(II)] top
Crystal data top
[Cd2(C7H14NS2)4(C12H10N4)]F(000) = 1172
Mr = 1140.39Dx = 1.477 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 16020 reflections
a = 9.0768 (16) Åθ = 1.8–40.5°
b = 11.137 (2) ŵ = 1.19 mm−1
c = 25.389 (5) ÅT = 98 K
β = 92.216 (3)°Prism, red
V = 2564.7 (8) Å30.35 × 0.12 × 0.10 mm
Z = 2
Data collection top
Rigaku AFC12κ/SATURN724
diffractometer		5861 independent reflections
Radiation source: fine-focus sealed tube5539 reflections with I > 2σ(I)
graphiteRint = 0.031
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −11→11
Tmin = 0.656, Tmax = 1k = −14→14
20914 measured reflectionsl = −32→31
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0362P)2 + 2.6654P]
where P = (Fo2 + 2Fc2)/3
5861 reflections(Δ/σ)max = 0.001
299 parametersΔρmax = 0.71 e Å−3
0 restraintsΔρmin = −0.72 e Å−3
Crystal data top
[Cd2(C7H14NS2)4(C12H10N4)]V = 2564.7 (8) Å3
Mr = 1140.39Z = 2
Monoclinic, P21/cMo Kα radiation
a = 9.0768 (16) ŵ = 1.19 mm−1
b = 11.137 (2) ÅT = 98 K
c = 25.389 (5) Å0.35 × 0.12 × 0.10 mm
β = 92.216 (3)°
Data collection top
Rigaku AFC12κ/SATURN724
diffractometer		5539 reflections with I > 2σ(I)
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		Rint = 0.031
Tmin = 0.656, Tmax = 1θmax = 27.5°
20914 measured reflectionsStandard reflections: 0
5861 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.077Δρmax = 0.71 e Å−3
S = 1.08Δρmin = −0.72 e Å−3
5861 reflectionsAbsolute structure: ?
299 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Cd0.153452 (17)0.407355 (14)0.605114 (6)0.01585 (6)
S10.07349 (7)0.19908 (6)0.56627 (3)0.03080 (16)
S20.37230 (6)0.24128 (5)0.61348 (3)0.02499 (14)
S3−0.06899 (6)0.53972 (6)0.63409 (2)0.02094 (12)
S40.19579 (6)0.48599 (5)0.70265 (2)0.01910 (12)
N2−0.0279 (2)0.6233 (2)0.73187 (8)0.0204 (4)
N30.3282 (2)0.53991 (17)0.56901 (8)0.0170 (4)
N40.06743 (19)0.50248 (18)0.51464 (7)0.0162 (4)
C10.2466 (2)0.1454 (2)0.58446 (9)0.0181 (4)
C20.1771 (3)−0.0570 (2)0.55108 (11)0.0278 (5)0.618 (8)
H2A0.2185−0.08700.51810.033*0.618 (8)
H2B0.0832−0.01560.54170.033*0.618 (8)
C30.1459 (5)−0.1621 (4)0.5862 (2)0.0325 (13)0.618 (8)
H3A0.0719−0.21410.56780.039*0.618 (8)
H3B0.2376−0.20960.59120.039*0.618 (8)
C40.0910 (4)−0.1317 (4)0.63923 (14)0.0540 (10)0.618 (8)
H4A0.0742−0.20570.65900.081*0.618 (8)
H4B−0.0017−0.08690.63510.081*0.618 (8)
H4C0.1644−0.08230.65850.081*0.618 (8)
C800.1771 (3)−0.0570 (2)0.55108 (11)0.0278 (5)0.382 (8)
H80A0.2327−0.12850.53990.033*0.382 (8)
H80B0.1301−0.02040.51910.033*0.382 (8)
C300.0531 (8)−0.0980 (6)0.5891 (3)0.031 (2)0.382 (8)
H30A−0.0184−0.03120.59120.037*0.382 (8)
H30B0.0002−0.16630.57200.037*0.382 (8)
C400.0910 (4)−0.1317 (4)0.63923 (14)0.0540 (10)0.382 (8)
H40A0.0021−0.15440.65760.081*0.382 (8)
H40B0.1398−0.06450.65780.081*0.382 (8)
H40C0.1584−0.20030.63850.081*0.382 (8)
N10.2807 (2)0.0299 (2)0.57585 (10)0.0293 (5)0.50
C50.4367 (6)−0.0111 (5)0.5768 (3)0.0210 (11)0.50
H5A0.50050.05390.56410.025*0.50
H5B0.4462−0.08120.55320.025*0.50
C60.4858 (5)−0.0460 (5)0.6335 (2)0.0235 (10)0.50
H6A0.46510.02090.65780.028*0.50
H6B0.4298−0.11730.64470.028*0.50
C70.6503 (6)−0.0740 (5)0.6360 (3)0.0325 (13)0.50
H7A0.6809−0.09630.67210.049*0.50
H7B0.7054−0.00290.62540.049*0.50
H7C0.6702−0.14070.61220.049*0.50
N100.2807 (2)0.0299 (2)0.57585 (10)0.0293 (5)0.50
C500.4217 (7)−0.0203 (5)0.6042 (3)0.0279 (13)0.50
H50A0.44660.02700.63630.033*0.50
H50B0.4068−0.10510.61440.033*0.50
C600.5433 (7)−0.0108 (5)0.5656 (3)0.0360 (13)0.50
H60A0.55450.07400.55470.043*0.50
H60B0.5169−0.05860.53370.043*0.50
C700.6906 (7)−0.0567 (6)0.5903 (3)0.0447 (16)0.50
H70A0.7677−0.05040.56450.067*0.50
H70B0.6797−0.14080.60090.067*0.50
H70C0.7180−0.00810.62140.067*0.50
C80.0275 (2)0.5569 (2)0.69392 (9)0.0178 (4)
C9−0.1698 (3)0.6864 (2)0.72549 (11)0.0263 (5)
H9A−0.18650.70860.68800.032*
H9B−0.16520.76150.74640.032*
C10−0.2992 (3)0.6109 (3)0.74297 (12)0.0355 (7)
H10A−0.28350.58870.78050.043*
H10B−0.30500.53600.72200.043*
C11−0.4437 (3)0.6802 (4)0.73570 (13)0.0472 (9)
H11A−0.52530.63040.74730.071*
H11B−0.46020.70070.69840.071*
H11C−0.43830.75400.75670.071*
C120.0537 (3)0.6428 (2)0.78277 (9)0.0234 (5)
H12A0.11230.57010.79180.028*
H12B−0.01770.65510.81080.028*
C130.1564 (3)0.7511 (2)0.78105 (10)0.0242 (5)
H13A0.09720.82530.77670.029*
H13B0.21980.74390.75030.029*
C140.2533 (3)0.7595 (3)0.83168 (11)0.0304 (6)
H14A0.31830.82950.82970.046*
H14B0.31310.68650.83570.046*
H14C0.19060.76780.86200.046*
C150.4586 (3)0.5575 (2)0.59424 (10)0.0202 (5)
H150.47440.52300.62820.024*
C160.5719 (3)0.6238 (2)0.57324 (10)0.0215 (5)
H160.66280.63420.59250.026*
C170.5501 (3)0.6745 (2)0.52364 (10)0.0227 (5)
H170.62620.71920.50800.027*
C180.4137 (3)0.6584 (2)0.49713 (9)0.0193 (4)
H180.39480.69300.46330.023*
C190.3063 (2)0.59112 (19)0.52103 (9)0.0161 (4)
C200.1614 (2)0.5730 (2)0.49415 (9)0.0169 (4)
H200.13760.61310.46190.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd0.01450 (9)0.01688 (9)0.01615 (10)0.00097 (6)0.00017 (6)−0.00067 (6)
S10.0254 (3)0.0220 (3)0.0437 (4)0.0073 (2)−0.0170 (3)−0.0097 (3)
S20.0160 (3)0.0172 (3)0.0413 (4)−0.0007 (2)−0.0038 (2)0.0019 (2)
S30.0162 (3)0.0263 (3)0.0201 (3)0.0040 (2)−0.0029 (2)−0.0056 (2)
S40.0159 (3)0.0221 (3)0.0192 (3)0.0031 (2)−0.0004 (2)−0.0007 (2)
N20.0146 (9)0.0258 (10)0.0207 (10)0.0011 (8)0.0002 (7)−0.0066 (8)
N30.0169 (9)0.0166 (9)0.0172 (9)0.0019 (7)−0.0018 (7)−0.0009 (7)
N40.0135 (9)0.0192 (9)0.0156 (9)−0.0008 (7)−0.0038 (7)−0.0006 (7)
C10.0185 (10)0.0167 (10)0.0193 (11)0.0003 (8)0.0025 (8)0.0035 (9)
C20.0275 (13)0.0207 (12)0.0348 (14)−0.0004 (10)−0.0021 (10)−0.0054 (11)
C30.031 (2)0.022 (2)0.045 (3)−0.0029 (18)−0.0006 (19)−0.0092 (19)
C40.046 (2)0.075 (3)0.0421 (19)−0.0291 (19)0.0068 (15)−0.0073 (18)
C800.0275 (13)0.0207 (12)0.0348 (14)−0.0004 (10)−0.0021 (10)−0.0054 (11)
C300.026 (4)0.022 (4)0.043 (4)−0.006 (3)−0.003 (3)−0.005 (3)
C400.046 (2)0.075 (3)0.0421 (19)−0.0291 (19)0.0068 (15)−0.0073 (18)
N10.0196 (10)0.0189 (10)0.0493 (14)0.0004 (8)−0.0019 (9)−0.0003 (10)
C50.014 (3)0.023 (3)0.026 (3)0.0064 (18)0.008 (2)−0.008 (3)
C60.013 (2)0.022 (2)0.034 (3)0.0030 (18)−0.011 (2)0.005 (2)
C70.019 (2)0.022 (2)0.056 (4)0.0074 (19)−0.011 (2)−0.012 (2)
N100.0196 (10)0.0189 (10)0.0493 (14)0.0004 (8)−0.0019 (9)−0.0003 (10)
C500.029 (3)0.020 (3)0.035 (4)0.004 (2)0.004 (3)−0.003 (3)
C600.037 (4)0.027 (3)0.044 (3)0.007 (2)−0.003 (3)0.002 (2)
C700.028 (3)0.037 (3)0.070 (5)0.006 (3)−0.001 (3)−0.006 (3)
C80.0148 (10)0.0182 (10)0.0206 (11)−0.0026 (8)0.0029 (8)−0.0004 (9)
C90.0171 (11)0.0322 (13)0.0294 (13)0.0073 (10)0.0000 (9)−0.0119 (11)
C100.0184 (12)0.0529 (18)0.0356 (15)0.0001 (12)0.0065 (10)−0.0130 (14)
C110.0168 (13)0.082 (3)0.0430 (17)0.0039 (14)0.0017 (11)−0.0247 (18)
C120.0218 (11)0.0296 (13)0.0188 (11)0.0009 (10)0.0001 (9)−0.0060 (10)
C130.0192 (11)0.0249 (12)0.0279 (13)0.0031 (9)−0.0042 (9)−0.0050 (10)
C140.0236 (12)0.0339 (14)0.0329 (14)0.0053 (11)−0.0082 (10)−0.0069 (11)
C150.0184 (11)0.0198 (11)0.0221 (11)0.0017 (9)−0.0051 (8)0.0007 (9)
C160.0154 (10)0.0198 (11)0.0288 (12)0.0000 (9)−0.0046 (9)−0.0037 (10)
C170.0180 (11)0.0181 (11)0.0319 (13)−0.0008 (9)0.0013 (9)−0.0005 (10)
C180.0191 (11)0.0177 (11)0.0212 (11)−0.0008 (8)0.0013 (8)0.0001 (9)
C190.0169 (10)0.0141 (10)0.0173 (11)0.0016 (8)0.0007 (8)−0.0030 (8)
C200.0164 (10)0.0187 (10)0.0156 (10)0.0022 (8)0.0002 (8)−0.0017 (8)
Geometric parameters (Å, °) top
Cd—N32.377 (2)C6—H6A0.9900
Cd—S12.6124 (8)C6—H6B0.9900
Cd—N42.6211 (19)C7—H7A0.9800
Cd—S32.6279 (7)C7—H7B0.9800
Cd—S42.6407 (7)C7—H7C0.9800
Cd—S22.7165 (7)N10—C501.548 (7)
S1—C11.727 (2)C50—C601.508 (9)
S2—C11.709 (2)C50—H50A0.9900
S3—C81.735 (2)C50—H50B0.9900
S4—C81.726 (2)C60—C701.543 (8)
N2—C81.329 (3)C60—H60A0.9900
N2—C91.470 (3)C60—H60B0.9900
N2—C121.480 (3)C70—H70A0.9800
N3—C151.338 (3)C70—H70B0.9800
N3—C191.353 (3)C70—H70C0.9800
N4—C201.284 (3)C9—C101.525 (4)
N4—N4i1.409 (3)C9—H9A0.9900
C1—N101.342 (3)C9—H9B0.9900
C1—N11.342 (3)C10—C111.527 (4)
C2—N11.474 (3)C10—H10A0.9900
C2—C31.505 (5)C10—H10B0.9900
C2—H2A0.9900C11—H11A0.9800
C2—H2B0.9900C11—H11B0.9800
C3—C41.493 (6)C11—H11C0.9800
C3—H3A0.9900C12—C131.526 (4)
C3—H3B0.9900C12—H12A0.9900
C4—H4A0.9800C12—H12B0.9900
C4—H4B0.9800C13—C141.532 (3)
C4—H4C0.9800C13—H13A0.9900
C80—N101.474 (3)C13—H13B0.9900
C80—C301.578 (8)C14—H14A0.9800
C80—H80A0.9900C14—H14B0.9800
C80—H80B0.9900C14—H14C0.9800
C30—C401.358 (9)C15—C161.389 (3)
C30—H30A0.9900C15—H150.9500
C30—H30B0.9900C16—C171.387 (4)
C40—H40A0.9800C16—H160.9500
C40—H40B0.9800C17—C181.398 (3)
C40—H40C0.9800C17—H170.9500
N1—C51.487 (5)C18—C191.388 (3)
C5—C61.539 (8)C18—H180.9500
C5—H5A0.9900C19—C201.472 (3)
C5—H5B0.9900C20—H200.9500
C6—C71.524 (7)
N3—Cd—S1125.86 (5)C6—C7—H7A109.5
N3—Cd—N465.89 (6)C6—C7—H7B109.5
S1—Cd—N487.65 (5)H7A—C7—H7B109.5
N3—Cd—S3106.92 (5)C6—C7—H7C109.5
S1—Cd—S3113.49 (2)H7A—C7—H7C109.5
N4—Cd—S379.19 (4)H7B—C7—H7C109.5
N3—Cd—S494.63 (5)C1—N10—C80123.5 (2)
S1—Cd—S4132.59 (2)C1—N10—C50117.5 (3)
N4—Cd—S4135.68 (5)C80—N10—C50117.6 (3)
S3—Cd—S468.714 (18)C60—C50—N10106.6 (6)
N3—Cd—S287.49 (5)C60—C50—H50A110.4
S1—Cd—S267.45 (2)N10—C50—H50A110.4
N4—Cd—S2122.40 (5)C60—C50—H50B110.4
S3—Cd—S2158.05 (2)N10—C50—H50B110.4
S4—Cd—S294.19 (2)H50A—C50—H50B108.6
C1—S1—Cd88.28 (8)C50—C60—C70110.9 (5)
C1—S2—Cd85.28 (8)C50—C60—H60A109.5
C8—S3—Cd86.54 (8)C70—C60—H60A109.5
C8—S4—Cd86.30 (8)C50—C60—H60B109.5
C8—N2—C9122.7 (2)C70—C60—H60B109.5
C8—N2—C12121.6 (2)H60A—C60—H60B108.1
C9—N2—C12115.64 (19)C60—C70—H70A109.5
C15—N3—C19117.8 (2)C60—C70—H70B109.5
C15—N3—Cd119.82 (16)H70A—C70—H70B109.5
C19—N3—Cd122.14 (15)C60—C70—H70C109.5
C20—N4—N4i112.8 (2)H70A—C70—H70C109.5
C20—N4—Cd114.97 (14)H70B—C70—H70C109.5
N4i—N4—Cd132.07 (19)N2—C8—S4121.29 (18)
N10—C1—N10.0 (2)N2—C8—S3120.26 (17)
N10—C1—S2120.96 (18)S4—C8—S3118.45 (13)
N1—C1—S2120.96 (18)N2—C9—C10112.7 (2)
N10—C1—S1120.08 (18)N2—C9—H9A109.1
N1—C1—S1120.08 (18)C10—C9—H9A109.1
S2—C1—S1118.96 (14)N2—C9—H9B109.1
N1—C2—C3112.9 (3)C10—C9—H9B109.1
N1—C2—H2A109.0H9A—C9—H9B107.8
C3—C2—H2A109.0C9—C10—C11110.7 (3)
N1—C2—H2B109.0C9—C10—H10A109.5
C3—C2—H2B109.0C11—C10—H10A109.5
H2A—C2—H2B107.8C9—C10—H10B109.5
C4—C3—C2115.8 (3)C11—C10—H10B109.5
C4—C3—H3A108.3H10A—C10—H10B108.1
C2—C3—H3A108.3C10—C11—H11A109.5
C4—C3—H3B108.3C10—C11—H11B109.5
C2—C3—H3B108.3H11A—C11—H11B109.5
H3A—C3—H3B107.4C10—C11—H11C109.5
C3—C4—H4A109.5H11A—C11—H11C109.5
C3—C4—H4B109.5H11B—C11—H11C109.5
H4A—C4—H4B109.5N2—C12—C13112.1 (2)
C3—C4—H4C109.5N2—C12—H12A109.2
H4A—C4—H4C109.5C13—C12—H12A109.2
H4B—C4—H4C109.5N2—C12—H12B109.2
N10—C80—C30112.8 (3)C13—C12—H12B109.2
N10—C80—H80A109.0H12A—C12—H12B107.9
C30—C80—H80A109.0C12—C13—C14110.9 (2)
N10—C80—H80B109.0C12—C13—H13A109.5
C30—C80—H80B109.0C14—C13—H13A109.5
H80A—C80—H80B107.8C12—C13—H13B109.5
C40—C30—C80119.5 (5)C14—C13—H13B109.5
C40—C30—H30A107.4H13A—C13—H13B108.1
C80—C30—H30A107.4C13—C14—H14A109.5
C40—C30—H30B107.4C13—C14—H14B109.5
C80—C30—H30B107.4H14A—C14—H14B109.5
H30A—C30—H30B107.0C13—C14—H14C109.5
C30—C40—H40A109.5H14A—C14—H14C109.5
C30—C40—H40B109.5H14B—C14—H14C109.5
H40A—C40—H40B109.5N3—C15—C16123.3 (2)
C30—C40—H40C109.5N3—C15—H15118.4
H40A—C40—H40C109.5C16—C15—H15118.4
H40B—C40—H40C109.5C17—C16—C15118.9 (2)
C1—N1—C2123.5 (2)C17—C16—H16120.6
C1—N1—C5121.2 (3)C15—C16—H16120.6
C2—N1—C5113.4 (3)C16—C17—C18118.5 (2)
N1—C5—C6109.6 (5)C16—C17—H17120.7
N1—C5—H5A109.8C18—C17—H17120.7
C6—C5—H5A109.8C19—C18—C17118.9 (2)
N1—C5—H5B109.8C19—C18—H18120.6
C6—C5—H5B109.8C17—C18—H18120.6
H5A—C5—H5B108.2N3—C19—C18122.7 (2)
C7—C6—C5109.8 (5)N3—C19—C20117.2 (2)
C7—C6—H6A109.7C18—C19—C20120.1 (2)
C5—C6—H6A109.7N4—C20—C19119.5 (2)
C7—C6—H6B109.7N4—C20—H20120.3
C5—C6—H6B109.7C19—C20—H20120.3
H6A—C6—H6B108.2
N3—Cd—S1—C169.94 (10)S1—C1—N1—C20.0 (4)
N4—Cd—S1—C1127.66 (9)N10—C1—N1—C50(100)
S3—Cd—S1—C1−155.19 (8)S2—C1—N1—C5−17.3 (5)
S4—Cd—S1—C1−73.14 (8)S1—C1—N1—C5162.8 (4)
S2—Cd—S1—C10.95 (8)C3—C2—N1—C1−120.0 (3)
N3—Cd—S2—C1−131.74 (9)C3—C2—N1—C576.1 (4)
S1—Cd—S2—C1−0.97 (8)C1—N1—C5—C688.3 (5)
N4—Cd—S2—C1−72.54 (9)C2—N1—C5—C6−107.3 (4)
S3—Cd—S2—C196.17 (9)N1—C5—C6—C7−173.3 (4)
S4—Cd—S2—C1133.80 (8)N1—C1—N10—C800(40)
N3—Cd—S3—C8−87.89 (9)S2—C1—N10—C80179.9 (2)
S1—Cd—S3—C8129.01 (8)S1—C1—N10—C800.0 (4)
N4—Cd—S3—C8−148.37 (9)N1—C1—N10—C500(100)
S4—Cd—S3—C80.51 (8)S2—C1—N10—C5013.8 (5)
S2—Cd—S3—C841.31 (10)S1—C1—N10—C50−166.1 (4)
N3—Cd—S4—C8105.86 (9)C30—C80—N10—C1−74.1 (4)
S1—Cd—S4—C8−103.38 (8)C30—C80—N10—C5092.0 (5)
N4—Cd—S4—C846.11 (10)C1—N10—C50—C60−95.8 (5)
S3—Cd—S4—C8−0.51 (8)C80—N10—C50—C6097.3 (5)
S2—Cd—S4—C8−166.33 (8)N10—C50—C60—C70179.0 (5)
S1—Cd—N3—C15−110.58 (17)C9—N2—C8—S4179.07 (19)
N4—Cd—N3—C15−178.32 (19)C12—N2—C8—S41.9 (3)
S3—Cd—N3—C15112.22 (17)C9—N2—C8—S3−0.9 (3)
S4—Cd—N3—C1543.08 (17)C12—N2—C8—S3−178.15 (18)
S2—Cd—N3—C15−50.92 (17)Cd—S4—C8—N2−179.2 (2)
S1—Cd—N3—C1963.49 (18)Cd—S4—C8—S30.82 (13)
N4—Cd—N3—C19−4.25 (16)Cd—S3—C8—N2179.2 (2)
S3—Cd—N3—C19−73.71 (17)Cd—S3—C8—S4−0.82 (13)
S4—Cd—N3—C19−142.85 (16)C8—N2—C9—C1090.9 (3)
S2—Cd—N3—C19123.15 (17)C12—N2—C9—C10−91.7 (3)
N3—Cd—N4—C201.00 (15)N2—C9—C10—C11179.9 (2)
S1—Cd—N4—C20−130.34 (16)C8—N2—C12—C1388.1 (3)
S3—Cd—N4—C20115.21 (16)C9—N2—C12—C13−89.3 (3)
S4—Cd—N4—C2071.62 (17)N2—C12—C13—C14−172.8 (2)
S2—Cd—N4—C20−69.06 (17)C19—N3—C15—C16−1.0 (3)
N3—Cd—N4—N4i−174.1 (3)Cd—N3—C15—C16173.34 (18)
S1—Cd—N4—N4i54.6 (3)N3—C15—C16—C17−0.1 (4)
S3—Cd—N4—N4i−59.9 (2)C15—C16—C17—C181.1 (4)
S4—Cd—N4—N4i−103.4 (2)C16—C17—C18—C19−0.9 (4)
S2—Cd—N4—N4i115.9 (2)C15—N3—C19—C181.1 (3)
Cd—S2—C1—N10−178.4 (2)Cd—N3—C19—C18−173.05 (17)
Cd—S2—C1—N1−178.4 (2)C15—N3—C19—C20−178.9 (2)
Cd—S2—C1—S11.54 (13)Cd—N3—C19—C206.9 (3)
Cd—S1—C1—N10178.3 (2)C17—C18—C19—N3−0.2 (3)
Cd—S1—C1—N1178.3 (2)C17—C18—C19—C20179.8 (2)
Cd—S1—C1—S2−1.60 (13)N4i—N4—C20—C19178.0 (2)
N1—C2—C3—C455.2 (4)Cd—N4—C20—C191.9 (3)
N10—C80—C30—C40−47.3 (7)N3—C19—C20—N4−5.7 (3)
S2—C1—N1—C2179.9 (2)C18—C19—C20—N4174.3 (2)
Symmetry codes: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···S4ii0.992.833.815 (3)171
C16—H16···S3iii0.952.823.674 (3)150
C3—H3B···Cgiv0.952.993.853 (5)147
Symmetry codes: (ii) −x, y+1/2, −z+3/2; (iii) x+1, y, z; (iv) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···S4i0.992.833.815 (3)171
C16—H16···S3ii0.952.823.674 (3)150
C3—H3B···Cgiii0.952.993.853 (5)147
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x+1, y, z; (iii) x, y−1, z.
references
References top

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Benson, R. E., Ellis, C. A., Lewis, C. E. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 930–940.

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.

Lai, C. S. & Tiekink, E. R. T. (2006). Z. Kristallogr. 221, 288–293.

Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Tiekink, E. R. T. (2006). CrystEngComm, 6, 104–118.