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(Acetonitrile-1κN)[μ-1H-benzimidazole-2(3H)-thione-1:2κ2S:S][1H-benzimidazole-2(3H)-thione-2κS]bis­(μ-1,1-dioxo-1λ6,2-benzothia­zole-3-thiol­ato)-1:2κ2S3:N;1:2κ2S3:S3-dicopper(I)(CuCu), [Cu2(C7H4NO2S2)2(C7H6N2S)2(CH3CN)] or [Cu2(tsac)2(Sbim)2(CH3CN)] [tsac is thio­saccharinate and Sbim is 1H-benzimidazole-2(3H)-thione], (I), is a new copper(I) compound that consists of a triply bridged dinuclear Cu—Cu unit. In the complex mol­ecule, two tsac anions and one neutral Sbim ligand bind the metals. One anion bridges via the endocyclic N and exocyclic S atoms (μ-S:N). The other anion and one of the mercaptobenzimidazole mol­ecules bridge the metals through their exocyclic S atoms (μ-S:S). The second Sbim ligand coordinates in a monodentate fashion (κS) to one Cu atom, while an acetonitrile mol­ecule coordinates to the other Cu atom. The CuI—CuI distance [2.6286 (6) Å] can be considered a strong `cuprophilic' inter­action. In the case of [μ-1H-benzimidazole-2(3H)-thione-1:2κ2S:S]bis­[1H-benzimidazole-2(3H)-thione]-1κS;2κS-bis­(μ-1,1-dioxo-1λ6,2-benzo­thia­zole-3-thiol­ato)-1:2κ2S3:N;1:2κ2S3:S3-dicopper(I)(CuCu), [Cu2(C7H4NO2S2)2(C7H6N2S)3] or [Cu2(tsac)2(Sbim)3], (II), the acetonitrile mol­ecule is substituted by an additional Sbim ligand, which binds one Cu atom via the exocylic S atom. In this case, the CuI—CuI distance is 2.6068 (11) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111052036/fn3087sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111052036/fn3087Isup4.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111052036/fn3087IIsup5.hkl
Contains datablock II

CCDC references: 866741; 866742

Comment top

Thionates, anions produced by the deprotonation of heterocyclic thioamides, can coordinate to metals, producing mononuclear or complex polynuclear species. Like other thioamides, thiosaccharin [or 1,1-dioxo-1λ6,2-benzothiazole-3(2H)-thione] is a versatile ligand, with the ability to coordinate metal centres in many ways (Dennehy et al., 2009). Particular attention has been devoted in recent decades to the synthesis of copper complexes, in both the mono- and divalent oxidation states, due to the great variety and flexibility of their coordination environments (Rapper, 1994). Most of the chemistry of CuI with thionates has been focused on the tetra- or hexanuclear binary complexes (García-Vázquez et al., 2005; Ruan & Shi, 2007; López-Torres et al., 2006). We have been working with binary and ternary copper thiosaccharinates, firstly synthesizing the Cu(tsac) complex (where tsac is the thiosaccharinate anion), which crystallized as the tetranuclear cluster [Cu4(tsac)4(CH3CN)2].2CH3CN from acetonitrile solutions (Dennehy et al., 2007), and then ternary phosphane complexes (Dennehy et al., 2009). To study the competition between two different thiones bound to copper, we have synthesized a ternary thiosaccharinate with thiosaccharin and 1H-benzimidazole-2(3H)-thione (Sbim), viz. [Cu2(tsac)2(Sbim)2(CH3CN)], (I), and [Cu2(tsac)2(Sbim)3], (II).

Compound (I) is a copper(I) thiosaccharinate and crystallizes in the space group P1. It is built of triply bridged dinuclear units. Two tsac anions and one Sbim molecule bind the metals. One anion bridges via the endocyclic N and exocyclic S atoms (µ-S:N), with Cu—N and Cu—S distances of 2.000 (2) and 2.2799 (9) Å, respectively. The other anion and one of the Sbim molecules bridge the metal centres through their exocyclic S atoms, with Cu—S distances of 2.3743 (9) and 2.6711 (10) Å for tsac, and 2.3785 (10) and 2.3901 (10) Å for Sbim. The second Sbim molecule coordinates in a monodentate fashion (κS), with a Cu—S distance of 2.2091 (10) Å, and the coordination of Cu2 is completed by an acetonitrile molecule, with a Cu—N distance of 1.964 (3) Å. Each CuI atom has a nearly distorted tetrahedral coordination environment. Given the proximity of the two CuI atoms, with a CuI—CuI distance of 2.6285 (6) Å, the two subunits form tetrahedra linked by edge-sharing. This short CuI—CuI distance indicates a strong cuprophilic interaction.

Each [Cu2(tsac)2(Sbim)2(CH3CN)] structural unit of (I) is stabilized by two intramolecular hydrogen bonds (N1D—H2DA···O1B and N1C—H1C···N1A) and one intermolecular hydrogen bond [N1D—H1DA···O1Ai; symmetry code: x, -y + 1, -z + 1], establishing an interaction with another inversion-symmetry related [Cu2(tsac)2(Sbim)2(CH3CN)] unit. The N2C—H2CA bond points towards a neighbouring Cu—Cu centre and away from acceptors. Therefore, it is blocked and unable to participate in any hydrogen bonds. Additionally, two Sbim and two tsac planar residues stack together through their six-membered planar rings in a four-layer group, with the negative tsac residues separated by the neutral Sbim molecules. There are also ππ interactions, with the rings arranged in the order tsaciii/Sbim/Sbimiv/tsacv [symmetry codes: (iii) x+1, y, z; (iv) -x+2, -y+1, -z; (v) -x+1, -y+1, -z]. Centroid–centroid distances are 3.588 (2) Å for tsaciii–Sbim (rings C1A–C6A and C1C–C6C, respectively) and equivalent Sbimiv–tsacv interactions; and 3.616 (2) Å between parallel Sbim–Sbimiv. The dihedral angle between tsac anions and nearby Sbim molecules is 12.53 (16)°.

Compound (II) crystallizes in the monoclinic space group P21/c. As mentioned before, this structure presents important similarities with the structure of (I). In the case of (II), the acetonitrile molecule is substituted by an additional disordered Sbim molecule, which binds to Cu from the exocyclic S atom (κS). In this case, the tsac anion bridges via the endocyclic N and exocyclic S atoms (µ-S:N), with Cu—N and Cu—S distances of 2.047 (4) and 2.3057 (17) Å, respectively. Each CuI atom presents a distorted tetrahedral coordination environment and both tetrahedra are linked by edge-sharing. The other anion and one of the Sbim molecules bridge the metal centres through their exocyclic S atoms, with Cu—S distances of 2.5470 (16) and 2.3261 (15) Å for tsac, and 2.4795 (15) and 2.3264 (15) Å for Sbim. The second Sbim molecule coordinates in a monodentate fashion (κS), with a Cu—S distance of 2.2748 (16) Å. An important difference between these two structures is the CuI—CuI distance; in the case of (II), the distance is 2.6068 (11) Å, which is slightly shorter than that in (I). Comparing the Cu—N distances, that in (I) is considerably shorter than that in (II), which leads to a weaker CuI—CuI interaction in (I). [Please check rephrasing - original text was not clear.]

The three-dimensional crystal structure of (II) is sustained by two intramolecular hydrogen bonds (N1C—H1C···N1A and N2DA—H2DA···O2B) and one intermolecular hydrogen bond (N1DA—H1DA···O1Av [symmetry code: (v) -x, -y + 1, -z] which correspond to a molecule related by inversion symmetry. The last two bonds involve the interaction between the disordered Sbim(D) molecule and two tsac molecules from two symmetry-related [Cu2(tsac)2(Sbim)3] units, as shown in Fig. 4. Finally, a possible intermolecular C—H···π interaction was identified as being responsible for the orientation of the Sbim(B) molecule, and responsible for the infinite packing along the plane defined by the [100] and [010] basis vectors. The C2E—H2E···Cg (Cg is the centroid of the S2B/N1B/C7B/C6B/C1B ring) angle is 162° and the H2E···Cg distance is 2.77 Å.

In order to compare the conformational geometries of (I) and (II), we performed a least-squares plane fitting of all the Sbim and tsac molecules in the two compounds, and the results are presented in Tables 1 and 2. The planes are constituted by atoms S1/S2/N1/C1/C2/C3/C4/C5 for Sbim and S1/N1/N2/C1/C2/C3/C4/C5/C6/C7 for tsac molecules. According to the calculations, the r.m.s. deviations of the fitted atoms are all below the limit of 0.0450 Å. A further comparison, assuming a common Cu1—Cu2 core, allows us to estimate the angles between the same kind of molecules in both conformations as 17.7, 14.2, 15.1 and 83.7° for tsac(A), tsac(B), Sbim(C) and Sbim(D), respectively (see Fig. 5). In the case of Sbim(D), we included the conformation with the higher site-occupation number, corresponding to Sbim(DA).

Related literature top

For related literature, see: Dennehy et al. (2007, 2009); García-Vázquez, Souza-Pedrares, Carabel, Romero & Souza (2005); López-Torres, Mendiola & Pastor (2006); Ruan & Shi (2007).

Experimental top

[Cu4(tsac)4(CH3CN)2].2CH3CN, (I), was synthesized as reported previously (Dennehy et al., 2007). [Cu2(tsac)2(Sbim)2(CH3CN)], (II), was synthesized by dropwise addition of a red solution of [Cu4(tsac)4(CH3CN)2].2CH3CN (10 mg, 0.04 mmol of Cu+) in CH3CN (5 ml) to another solution of 2-mercaptobenzimidazole (6 mg, 0.04 mmol) in CH3CN (4 ml) with mechanical stirring. The solution turned orange. After a day of slow evaporation of the solvent, red crystals of (II) suitable for X-ray diffraction studies were obtained. The crystals were washed with diethyl ether and were air stable. Compound (II) was synthesized employing different molar ratios of (I) and Sbim (Cu:Sbim = 1:1, 1:4, 1:10) in CH3CN solutions. When the molar ratio was 1:1 to 1:4, crystals of the title compounds were obtained as unique products. When the Cu:Sbim ratio was 1:10, a very few thin orange needles of (II) were obtained. Analysis, calculated for C30H23Cu2N7O4S6: C 41.6, H 2.6, N 11.3%; found: C 41.6, H 2.3, N 11.3%. IR spectra were obtained in KBr dispersion and in Nujol mulls, and showed no differences in the vibrational bands. The IR spectra of this complex confirm the presence of two different thiosaccharinate anions. Selected anion bands, KBr (cm-1): 1394 (w)/1355 (s), 1258 (s), 1234/1222 (w), 1149 (vs), 1118 (m), 1022 (vw)/1008 (m), 837 (m)/822 (m), 622 (w). The UV–Vis spectra of the solid complex presents broad bands (200/214/245 and 298/310 nm) that are assigned to transitions in the phenyl groups and in the thiocarbonilic bonds within the ligands.

Refinement top

For (I), the H atoms were positioned geometrically and treated as riding, with C—H = 0.93–0.96 Å and N—H = 0.86 Å. H atoms bonded to tertiary C atoms were refined with Uiso(H) = 1.2Ueq(C), while for the methyl groups Uiso(H) = 1.5Ueq(C). The anisotropic displacement ellipsoid of atom S1D displays a marked elongation in the normal direction to both the S—C and S—Cu bonds. This can be related to the motion of the corresponding Sbim molecule, which coordinates to Cu via only one bond through atom S1D. The highest residual electron-density peak is located 0.79 Å from atom S1D.

In the case of (II), refinement proceeded in a similar manner. The main difference arises in the treatment of the disordered Sbim(D) molecule, which was refined in two orientations. The atomic displacements for Sbim(D) were refined isotropically because of the proximity between atoms belonging to the two disordered positions. Anisotropic treatment of the atomic displacement did not provide better statistics considering the increase of variables in the refinement. Finally, the distance between the closest atoms in the Sbim(D) molecule were restrained to the average distance of the rest of the Sbim molecules in the complex. The C7—N1 and C7—N2 distances were restrained to 1.33 Å and the N1—N2 distance was restrained to 2.145 Å. The position of the highest residual electron-density peak is located 2.44 Å from atom H4DA.

Computing details top

For both compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury [Version 1.4.2 (Build 2); Macrae et al., 2008]; software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The structure of [Cu2(tsac)2(Sbim)2(CH3CN)], (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines idicate the intramolecular hydrogen bonds. [Please check added text]
[Figure 2] Fig. 2. A view of the packing of (I), normal to the [100] direction, showing the intra- and intermolecular hydrogen bonds as dashed lines (cyan in the electronic version of the paper).
[Figure 3] Fig. 3. The structure of [Cu2(tsac)2(Sbim)3)], (II), showing the atom-labelling scheme, indicating the two disordered Sbim molecules. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 4] Fig. 4. A partial view of the packing of (II), normal to the [110] direction. Dashed lines indicate the hydrogen-bond interactions between [Cu2(tsac)2(Sbim)3)] units (cyan in the electronic version of the paper) and the connections between them as a result of C—H···π interactions (green). One of the disordered Sbim molecules has been omitted for clarity.
[Figure 5] Fig. 5. The overlap of [Cu2(tsac)2(Sbim)2(CH3CN)] (dashed lines) and [Cu2(tsac)2(Sbim)3] (solid lines) after a least-squares fit of atoms Cu1, Cu2, S1A, S1B, C7B, N1B and S1C. The letter A indicates the tsac(A) molecule, B the tsac(B) molecule, C the Sbim(C) molecule and D the Sbim(D) molecule.
(I) (Acetonitrile-1κN)[µ-1H-benzimidazole-2(3H)-thione- 1:2κ2S:S][1H-benzimidazole-2(3H)-thione- 2κS]bis(µ-1,1-dioxo-1λ6,2-benzothiazole-3-thiolato)- 1:2κ2S3:N;1:2κ2S3:S3- dicopper(I)(CuCu) top
Crystal data top
[Cu2(C7H4NO2S2)2(C7H6N2S)2(C2H3N)]Z = 2
Mr = 865.01F(000) = 876
Triclinic, P1Dx = 1.715 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0466 (1) ÅCell parameters from 34323 reflections
b = 13.8150 (2) Åθ = 3.6–29.0°
c = 15.3621 (2) ŵ = 1.69 mm1
α = 87.739 (1)°T = 293 K
β = 89.480 (1)°Plate, orange
γ = 79.033 (1)°0.30 × 0.20 × 0.10 mm
V = 1675.21 (4) Å3
Data collection top
Oxford Xcalibur Eos Gemini
diffractometer
8285 independent reflections
Radiation source: Enhance (Mo) X-ray Source5570 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 16.1158 pixels mm-1θmax = 29.1°, θmin = 3.6°
ω scans, thick slicesh = 1010
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 1818
Tmin = 0.716, Tmax = 0.801l = 2020
97442 measured reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0557P)2 + 0.8876P]
where P = (Fo2 + 2Fc2)/3
8285 reflections(Δ/σ)max < 0.001
443 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.65 e Å3
0 constraints
Crystal data top
[Cu2(C7H4NO2S2)2(C7H6N2S)2(C2H3N)]γ = 79.033 (1)°
Mr = 865.01V = 1675.21 (4) Å3
Triclinic, P1Z = 2
a = 8.0466 (1) ÅMo Kα radiation
b = 13.8150 (2) ŵ = 1.69 mm1
c = 15.3621 (2) ÅT = 293 K
α = 87.739 (1)°0.30 × 0.20 × 0.10 mm
β = 89.480 (1)°
Data collection top
Oxford Xcalibur Eos Gemini
diffractometer
8285 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
5570 reflections with I > 2σ(I)
Tmin = 0.716, Tmax = 0.801Rint = 0.046
97442 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.10Δρmax = 0.50 e Å3
8285 reflectionsΔρmin = 0.65 e Å3
443 parameters
Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/Ueq
Cu10.67554 (5)0.61946 (3)0.39313 (3)0.04144 (12)
Cu20.53872 (6)0.74039 (3)0.26582 (3)0.05018 (14)
S1B0.58063 (11)0.72928 (6)0.49776 (5)0.0396 (2)
S2A0.64788 (10)0.31860 (6)0.22573 (6)0.0405 (2)
S2B0.29075 (10)0.92876 (6)0.32946 (5)0.03420 (18)
S1A0.42920 (11)0.58106 (6)0.32965 (5)0.03798 (19)
S1C0.83493 (11)0.70616 (6)0.29731 (6)0.0413 (2)
N1B0.4306 (3)0.82974 (17)0.35820 (15)0.0318 (6)
C7B0.4556 (4)0.8228 (2)0.44401 (19)0.0293 (6)
O1B0.3684 (3)0.99138 (16)0.27139 (14)0.0458 (6)
N1A0.6375 (3)0.4325 (2)0.25543 (18)0.0392 (6)
N1D0.3392 (5)0.8356 (2)0.01325 (18)0.0535 (8)
H1DA0.34780.78440.04420.064*
C1B0.2627 (4)0.9753 (2)0.43408 (19)0.0327 (6)
N1C0.8893 (3)0.54599 (19)0.19383 (16)0.0344 (6)
H1C0.79780.52590.20840.041*
C7C0.9355 (4)0.6266 (2)0.2226 (2)0.0347 (7)
O1A0.6731 (4)0.3143 (2)0.13315 (18)0.0601 (7)
C7A0.4871 (4)0.4680 (2)0.28895 (19)0.0321 (6)
C6B0.3604 (4)0.9079 (2)0.49073 (19)0.0308 (6)
O2B0.1414 (3)0.9013 (2)0.29776 (17)0.0548 (7)
N2C1.0826 (3)0.6351 (2)0.18357 (19)0.0412 (6)
H2CA1.13600.68260.19040.049*
C7D0.3908 (5)0.8345 (3)0.0698 (2)0.0459 (9)
C3A0.1899 (5)0.2473 (3)0.2725 (2)0.0447 (8)
H3A0.12760.19760.26690.054*
O2A0.7673 (3)0.25142 (19)0.2784 (2)0.0603 (7)
C6A0.3665 (4)0.3980 (2)0.28957 (19)0.0318 (6)
C2B0.1632 (4)1.0609 (2)0.4620 (2)0.0433 (8)
H2B0.09851.10590.42320.052*
C4A0.1140 (4)0.3352 (3)0.3084 (2)0.0446 (8)
H4A0.00130.34360.32580.053*
C5B0.3598 (4)0.9250 (2)0.5785 (2)0.0392 (7)
H5B0.42450.88000.61730.047*
C5C1.0257 (5)0.4124 (3)0.0933 (2)0.0442 (8)
H5C0.94230.37420.09690.053*
C3B0.1636 (5)1.0772 (2)0.5505 (2)0.0442 (8)
H3B0.09741.13400.57160.053*
C6C1.0107 (4)0.4991 (2)0.1367 (2)0.0351 (7)
C5A0.2018 (4)0.4109 (2)0.3189 (2)0.0375 (7)
H5A0.15110.46870.34510.045*
N2D0.3557 (4)0.9281 (2)0.09472 (18)0.0476 (7)
H2DA0.37730.94700.14540.057*
C1A0.4399 (4)0.3100 (2)0.2535 (2)0.0340 (7)
C4B0.2605 (5)1.0107 (2)0.6075 (2)0.0442 (8)
H4B0.25911.02360.66650.053*
C1C1.1356 (4)0.5558 (3)0.1307 (2)0.0398 (7)
C2A0.3574 (4)0.2318 (2)0.2446 (2)0.0394 (7)
H2A0.41060.17260.22150.047*
C4C1.1697 (5)0.3850 (3)0.0443 (2)0.0527 (9)
H4C1.18410.32680.01430.063*
C1D0.2705 (5)0.9307 (3)0.0420 (2)0.0510 (9)
C6D0.2796 (5)0.9902 (3)0.0273 (2)0.0484 (9)
C2D0.1985 (6)0.9682 (3)0.1200 (3)0.0682 (13)
H2D0.19060.92770.16610.082*
C3C1.2937 (5)0.4420 (3)0.0386 (3)0.0597 (11)
H3C1.38970.42080.00520.072*
C5D0.2200 (7)1.0907 (3)0.0208 (3)0.0706 (13)
H5D0.22701.13110.06710.085*
C2C1.2794 (5)0.5281 (3)0.0806 (3)0.0568 (10)
H2C1.36240.56660.07590.068*
C4D0.1494 (8)1.1283 (3)0.0581 (3)0.0889 (17)
H4D0.10811.19570.06500.107*
C3D0.1386 (7)1.0684 (4)0.1267 (3)0.0810 (16)
H3D0.08961.09630.17860.097*
S1D0.47787 (18)0.73062 (7)0.12689 (6)0.0683 (3)
N1S0.7954 (4)0.4923 (2)0.4425 (2)0.0484 (7)
C1S0.8343 (4)0.4153 (3)0.4720 (2)0.0424 (8)
C2S0.8855 (5)0.3149 (3)0.5064 (3)0.0598 (11)
H2S10.83480.27140.47250.090*
H2S20.84920.31080.56590.090*
H2S31.00650.29610.50350.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0497 (3)0.0292 (2)0.0422 (2)0.00143 (17)0.00238 (19)0.00406 (16)
Cu20.0598 (3)0.0529 (3)0.0304 (2)0.0106 (2)0.00513 (19)0.01216 (18)
S1B0.0538 (5)0.0308 (4)0.0294 (4)0.0042 (3)0.0064 (4)0.0019 (3)
S2A0.0360 (4)0.0404 (4)0.0497 (5)0.0156 (4)0.0087 (4)0.0183 (4)
S2B0.0419 (4)0.0321 (4)0.0259 (4)0.0007 (3)0.0061 (3)0.0040 (3)
S1A0.0396 (4)0.0331 (4)0.0421 (4)0.0077 (3)0.0011 (3)0.0073 (3)
S1C0.0443 (5)0.0393 (4)0.0426 (5)0.0125 (4)0.0018 (4)0.0072 (3)
N1B0.0408 (15)0.0268 (12)0.0258 (12)0.0000 (10)0.0041 (11)0.0051 (10)
C7B0.0340 (16)0.0256 (13)0.0285 (14)0.0055 (12)0.0033 (12)0.0046 (11)
O1B0.0725 (17)0.0356 (12)0.0278 (11)0.0063 (11)0.0005 (11)0.0003 (9)
N1A0.0407 (16)0.0397 (15)0.0433 (15)0.0206 (12)0.0120 (12)0.0148 (12)
N1D0.093 (3)0.0424 (16)0.0292 (15)0.0208 (16)0.0111 (15)0.0082 (12)
C1B0.0399 (17)0.0297 (14)0.0283 (15)0.0060 (13)0.0000 (13)0.0037 (12)
N1C0.0295 (13)0.0407 (14)0.0351 (14)0.0123 (11)0.0041 (11)0.0013 (11)
C7C0.0320 (16)0.0412 (17)0.0321 (16)0.0106 (13)0.0027 (13)0.0028 (13)
O1A0.0662 (18)0.0663 (17)0.0571 (16)0.0315 (14)0.0236 (14)0.0321 (14)
C7A0.0375 (17)0.0346 (15)0.0263 (14)0.0121 (13)0.0008 (13)0.0030 (12)
C6B0.0360 (17)0.0277 (14)0.0292 (15)0.0061 (12)0.0009 (12)0.0068 (11)
O2B0.0464 (15)0.0697 (17)0.0473 (15)0.0052 (13)0.0145 (12)0.0146 (13)
N2C0.0349 (15)0.0439 (16)0.0484 (17)0.0165 (12)0.0025 (13)0.0005 (13)
C7D0.074 (3)0.0426 (19)0.0247 (16)0.0194 (17)0.0024 (16)0.0044 (13)
C3A0.048 (2)0.051 (2)0.0421 (19)0.0297 (17)0.0109 (16)0.0084 (16)
O2A0.0364 (14)0.0490 (15)0.096 (2)0.0073 (11)0.0033 (14)0.0096 (14)
C6A0.0331 (16)0.0358 (16)0.0276 (15)0.0100 (13)0.0045 (12)0.0012 (12)
C2B0.052 (2)0.0331 (16)0.0400 (18)0.0053 (14)0.0006 (15)0.0013 (14)
C4A0.0335 (18)0.062 (2)0.0410 (19)0.0178 (16)0.0055 (15)0.0082 (16)
C5B0.049 (2)0.0357 (16)0.0309 (16)0.0017 (14)0.0046 (14)0.0028 (13)
C5C0.050 (2)0.0472 (19)0.0375 (18)0.0137 (16)0.0054 (15)0.0018 (15)
C3B0.057 (2)0.0310 (16)0.0417 (19)0.0010 (15)0.0064 (16)0.0095 (14)
C6C0.0330 (17)0.0407 (17)0.0311 (16)0.0069 (13)0.0032 (13)0.0042 (13)
C5A0.0342 (17)0.0435 (18)0.0348 (17)0.0081 (14)0.0019 (14)0.0017 (14)
N2D0.079 (2)0.0379 (15)0.0285 (14)0.0163 (15)0.0094 (14)0.0047 (11)
C1A0.0314 (16)0.0378 (16)0.0352 (16)0.0125 (13)0.0039 (13)0.0009 (13)
C4B0.060 (2)0.0444 (19)0.0280 (16)0.0075 (16)0.0046 (15)0.0125 (14)
C1C0.0346 (17)0.0458 (18)0.0397 (18)0.0108 (14)0.0033 (14)0.0039 (14)
C2A0.0423 (19)0.0393 (17)0.0404 (18)0.0169 (15)0.0054 (15)0.0005 (14)
C4C0.058 (2)0.053 (2)0.044 (2)0.0025 (18)0.0070 (18)0.0067 (17)
C1D0.073 (3)0.048 (2)0.0374 (19)0.0261 (19)0.0116 (18)0.0009 (16)
C6D0.074 (3)0.0459 (19)0.0282 (16)0.0186 (18)0.0102 (17)0.0009 (14)
C2D0.110 (4)0.066 (3)0.034 (2)0.031 (3)0.023 (2)0.0048 (18)
C3C0.049 (2)0.072 (3)0.056 (2)0.005 (2)0.0179 (19)0.008 (2)
C5D0.117 (4)0.046 (2)0.051 (2)0.019 (2)0.025 (3)0.0038 (18)
C2C0.041 (2)0.071 (3)0.062 (3)0.0200 (19)0.0142 (18)0.002 (2)
C4D0.141 (5)0.050 (3)0.075 (3)0.017 (3)0.042 (3)0.013 (2)
C3D0.124 (4)0.069 (3)0.054 (3)0.031 (3)0.041 (3)0.016 (2)
S1D0.1312 (11)0.0366 (5)0.0328 (5)0.0027 (6)0.0185 (6)0.0076 (4)
N1S0.0521 (18)0.0406 (16)0.0467 (17)0.0055 (13)0.0024 (14)0.0006 (13)
C1S0.0385 (18)0.0402 (18)0.0448 (19)0.0022 (14)0.0035 (15)0.0033 (15)
C2S0.065 (3)0.042 (2)0.065 (3)0.0068 (18)0.005 (2)0.0107 (18)
Geometric parameters (Å, º) top
Cu1—N1S1.964 (3)C6A—C5A1.377 (4)
Cu1—S1B2.2799 (9)C6A—C1A1.381 (4)
Cu1—S1A2.3743 (9)C2B—C3B1.386 (5)
Cu1—S1C2.3785 (10)C2B—H2B0.9300
Cu1—Cu22.6285 (6)C4A—C5A1.384 (5)
Cu2—N1B2.000 (2)C4A—H4A0.9300
Cu2—S1D2.2091 (10)C5B—C4B1.383 (4)
Cu2—S1C2.3901 (10)C5B—H5B0.9300
Cu2—S1A2.6711 (10)C5C—C4C1.375 (5)
S1B—C7B1.673 (3)C5C—C6C1.379 (5)
S2A—O2A1.433 (3)C5C—H5C0.9300
S2A—O1A1.437 (3)C3B—C4B1.377 (5)
S2A—N1A1.642 (3)C3B—H3B0.9300
S2A—C1A1.748 (3)C6C—C1C1.388 (5)
S2B—O2B1.423 (3)C5A—H5A0.9300
S2B—O1B1.438 (2)N2D—C6D1.389 (4)
S2B—N1B1.646 (2)N2D—H2DA0.8600
S2B—C1B1.751 (3)C1A—C2A1.384 (4)
S1A—C7A1.687 (3)C4B—H4B0.9300
S1C—C7C1.710 (3)C1C—C2C1.384 (5)
N1B—C7B1.332 (4)C2A—H2A0.9300
C7B—C6B1.483 (4)C4C—C3C1.384 (6)
N1A—C7A1.324 (4)C4C—H4C0.9300
N1D—C7D1.345 (4)C1D—C2D1.375 (5)
N1D—C1D1.381 (5)C1D—C6D1.381 (5)
N1D—H1DA0.8600C6D—C5D1.380 (5)
C1B—C2B1.378 (4)C2D—C3D1.376 (6)
C1B—C6B1.383 (4)C2D—H2D0.9300
N1C—C7C1.331 (4)C3C—C2C1.360 (6)
N1C—C6C1.390 (4)C3C—H3C0.9300
N1C—H1C0.8600C5D—C4D1.382 (6)
C7C—N2C1.345 (4)C5D—H5D0.9300
C7A—C6A1.494 (4)C2C—H2C0.9300
C6B—C5B1.378 (4)C4D—C3D1.379 (7)
N2C—C1C1.388 (4)C4D—H4D0.9300
N2C—H2CA0.8600C3D—H3D0.9300
C7D—N2D1.339 (4)N1S—C1S1.128 (4)
C7D—S1D1.688 (4)C1S—C2S1.449 (5)
C3A—C4A1.385 (5)C2S—H2S10.9600
C3A—C2A1.390 (5)C2S—H2S20.9600
C3A—H3A0.9300C2S—H2S30.9600
N1S—Cu1—S1B112.41 (9)C5A—C6A—C7A129.5 (3)
N1S—Cu1—S1A103.95 (10)C1A—C6A—C7A110.9 (3)
S1B—Cu1—S1A105.73 (3)C1B—C2B—C3B117.1 (3)
N1S—Cu1—S1C116.16 (10)C1B—C2B—H2B121.5
S1B—Cu1—S1C104.04 (3)C3B—C2B—H2B121.5
S1A—Cu1—S1C114.30 (3)C5A—C4A—C3A121.5 (3)
N1S—Cu1—Cu2154.15 (9)C5A—C4A—H4A119.2
S1B—Cu1—Cu293.28 (2)C3A—C4A—H4A119.2
S1A—Cu1—Cu264.31 (3)C6B—C5B—C4B118.3 (3)
S1C—Cu1—Cu256.76 (3)C6B—C5B—H5B120.8
N1B—Cu2—S1D132.11 (8)C4B—C5B—H5B120.8
N1B—Cu2—S1C105.88 (8)C4C—C5C—C6C117.0 (3)
S1D—Cu2—S1C114.20 (5)C4C—C5C—H5C121.5
N1B—Cu2—Cu186.83 (7)C6C—C5C—H5C121.5
S1D—Cu2—Cu1137.19 (3)C4B—C3B—C2B121.2 (3)
S1C—Cu2—Cu156.34 (2)C4B—C3B—H3B119.4
N1B—Cu2—S1A95.33 (8)C2B—C3B—H3B119.4
S1D—Cu2—S1A99.20 (4)C5C—C6C—C1C121.2 (3)
S1C—Cu2—S1A104.02 (3)C5C—C6C—N1C132.4 (3)
Cu1—Cu2—S1A53.23 (2)C1C—C6C—N1C106.3 (3)
C7B—S1B—Cu1104.36 (10)C6A—C5A—C4A118.1 (3)
O2A—S2A—O1A116.16 (18)C6A—C5A—H5A121.0
O2A—S2A—N1A110.71 (16)C4A—C5A—H5A121.0
O1A—S2A—N1A109.42 (16)C7D—N2D—C6D110.5 (3)
O2A—S2A—C1A111.23 (16)C7D—N2D—H2DA124.8
O1A—S2A—C1A110.93 (16)C6D—N2D—H2DA124.8
N1A—S2A—C1A96.68 (14)C6A—C1A—C2A123.8 (3)
O2B—S2B—O1B115.58 (15)C6A—C1A—S2A107.2 (2)
O2B—S2B—N1B110.19 (15)C2A—C1A—S2A129.0 (3)
O1B—S2B—N1B109.61 (14)C3B—C4B—C5B121.1 (3)
O2B—S2B—C1B112.12 (16)C3B—C4B—H4B119.5
O1B—S2B—C1B111.82 (14)C5B—C4B—H4B119.5
N1B—S2B—C1B95.73 (13)C2C—C1C—C6C121.4 (3)
C7A—S1A—Cu1106.49 (11)C2C—C1C—N2C132.6 (3)
C7A—S1A—Cu2123.48 (11)C6C—C1C—N2C106.0 (3)
Cu1—S1A—Cu262.47 (2)C1A—C2A—C3A115.7 (3)
C7C—S1C—Cu1108.83 (11)C1A—C2A—H2A122.1
C7C—S1C—Cu2108.56 (11)C3A—C2A—H2A122.1
Cu1—S1C—Cu266.90 (3)C5C—C4C—C3C121.5 (4)
C7B—N1B—S2B111.6 (2)C5C—C4C—H4C119.2
C7B—N1B—Cu2129.40 (19)C3C—C4C—H4C119.2
S2B—N1B—Cu2118.97 (13)C2D—C1D—C6D121.7 (4)
N1B—C7B—C6B113.5 (2)C2D—C1D—N1D131.9 (4)
N1B—C7B—S1B125.4 (2)C6D—C1D—N1D106.4 (3)
C6B—C7B—S1B121.1 (2)C5D—C6D—C1D121.5 (3)
C7A—N1A—S2A110.8 (2)C5D—C6D—N2D132.5 (3)
C7D—N1D—C1D110.5 (3)C1D—C6D—N2D106.0 (3)
C7D—N1D—H1DA124.8C1D—C2D—C3D117.0 (4)
C1D—N1D—H1DA124.8C1D—C2D—H2D121.5
C2B—C1B—C6B122.3 (3)C3D—C2D—H2D121.5
C2B—C1B—S2B130.1 (2)C2C—C3C—C4C121.9 (4)
C6B—C1B—S2B107.6 (2)C2C—C3C—H3C119.0
C7C—N1C—C6C110.0 (3)C4C—C3C—H3C119.0
C7C—N1C—H1C125.0C6D—C5D—C4D116.6 (4)
C6C—N1C—H1C125.0C6D—C5D—H5D121.7
N1C—C7C—N2C107.7 (3)C4D—C5D—H5D121.7
N1C—C7C—S1C128.2 (2)C3C—C2C—C1C117.0 (4)
N2C—C7C—S1C124.2 (2)C3C—C2C—H2C121.5
N1A—C7A—C6A114.3 (3)C1C—C2C—H2C121.5
N1A—C7A—S1A125.1 (2)C3D—C4D—C5D121.7 (4)
C6A—C7A—S1A120.6 (2)C3D—C4D—H4D119.1
C5B—C6B—C1B120.1 (3)C5D—C4D—H4D119.1
C5B—C6B—C7B128.5 (3)C2D—C3D—C4D121.5 (4)
C1B—C6B—C7B111.4 (3)C2D—C3D—H3D119.3
C7C—N2C—C1C110.0 (3)C4D—C3D—H3D119.3
C7C—N2C—H2CA125.0C7D—S1D—Cu2118.95 (12)
C1C—N2C—H2CA125.0C1S—N1S—Cu1166.9 (3)
N2D—C7D—N1D106.7 (3)N1S—C1S—C2S177.6 (4)
N2D—C7D—S1D129.8 (3)C1S—C2S—H2S1109.5
N1D—C7D—S1D123.6 (3)C1S—C2S—H2S2109.5
C4A—C3A—C2A121.3 (3)H2S1—C2S—H2S2109.5
C4A—C3A—H3A119.4C1S—C2S—H2S3109.5
C2A—C3A—H3A119.4H2S1—C2S—H2S3109.5
C5A—C6A—C1A119.6 (3)H2S2—C2S—H2S3109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1D—H1DA···O1Ai0.862.002.841 (4)167
N1C—H1C···N1A0.862.102.918 (4)160
N2D—H2DA···O1B0.862.052.893 (4)166
Symmetry code: (i) x+1, y+1, z.
(II) [µ-1H-benzimidazole-2(3H)-thione- 1:2κ2S:S]bis[1H-benzimidazole-2(3H)-thione]- 1κS;2κS-bis(µ-1,1-dioxo-1λ6,2-benzothiazole-3-thiolato)- 1:2κ2S3:N;1:2κ2S3:S3- dicopper(I)(CuCu) top
Crystal data top
[Cu2(C7H4NO2S2)2(C7H6N2S)3]F(000) = 1976
Mr = 974.14Dx = 1.613 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2072 reflections
a = 13.2395 (12) Åθ = 3.7–29.0°
b = 10.2731 (10) ŵ = 1.48 mm1
c = 29.536 (15) ÅT = 293 K
β = 93.135 (16)°Needle, red
V = 4011 (2) Å30.25 × 0.15 × 0.10 mm
Z = 4
Data collection top
Oxford Xcalibur Eos Gemini
diffractometer
8812 independent reflections
Radiation source: Enhance (Mo) X-ray Source4863 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
Detector resolution: 16.1158 pixels mm-1θmax = 27.5°, θmin = 3.7°
ω scans, thick slicesh = 1717
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 713
Tmin = 0.814, Tmax = 0.867l = 3438
18885 measured reflections
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0565P)2 + 0.3051P]
where P = (Fo2 + 2Fc2)/3
8812 reflections(Δ/σ)max < 0.001
587 parametersΔρmax = 0.78 e Å3
317 restraintsΔρmin = 0.39 e Å3
0 constraints
Crystal data top
[Cu2(C7H4NO2S2)2(C7H6N2S)3]V = 4011 (2) Å3
Mr = 974.14Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.2395 (12) ŵ = 1.48 mm1
b = 10.2731 (10) ÅT = 293 K
c = 29.536 (15) Å0.25 × 0.15 × 0.10 mm
β = 93.135 (16)°
Data collection top
Oxford Xcalibur Eos Gemini
diffractometer
8812 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
4863 reflections with I > 2σ(I)
Tmin = 0.814, Tmax = 0.867Rint = 0.066
18885 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067317 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.01Δρmax = 0.78 e Å3
8812 reflectionsΔρmin = 0.39 e Å3
587 parameters
Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/UeqOcc. (<1)
Cu10.45898 (5)0.29325 (7)0.06351 (2)0.0462 (2)
Cu20.29961 (5)0.19343 (7)0.09829 (2)0.0477 (2)
S2A0.16473 (11)0.53028 (13)0.02790 (4)0.0388 (3)
S1A0.33525 (11)0.43466 (13)0.08724 (4)0.0407 (3)
N1A0.2332 (3)0.4332 (4)0.00611 (12)0.0356 (10)
O2A0.2242 (3)0.5729 (4)0.06449 (11)0.0550 (11)
O1A0.0702 (3)0.4702 (3)0.04161 (12)0.0507 (10)
C1A0.1518 (4)0.6578 (5)0.01085 (16)0.0342 (12)
C2A0.1034 (4)0.7758 (5)0.00591 (18)0.0430 (13)
H2A0.06520.79650.02050.052*
C5A0.2208 (4)0.7131 (5)0.08459 (16)0.0416 (13)
H5A0.25960.69300.11090.050*
C6A0.2109 (4)0.6253 (5)0.04947 (15)0.0322 (11)
C7A0.2575 (4)0.4936 (5)0.04479 (15)0.0329 (12)
S2B0.34219 (12)0.06820 (15)0.19724 (4)0.0486 (4)
O1B0.3195 (4)0.0613 (4)0.18141 (14)0.0730 (13)
O2B0.2613 (3)0.1388 (5)0.21697 (12)0.0668 (13)
S1B0.55635 (11)0.26931 (15)0.13012 (4)0.0468 (4)
N1B0.3876 (3)0.1568 (4)0.15603 (12)0.0378 (10)
C1B0.4531 (4)0.0747 (5)0.23276 (16)0.0438 (14)
C2B0.4724 (6)0.0209 (6)0.27513 (19)0.0658 (19)
H2B0.42400.02900.28880.079*
C3B0.5659 (7)0.0436 (7)0.2964 (2)0.078 (2)
H3B0.58130.00940.32520.093*
C4B0.6364 (6)0.1164 (7)0.2755 (2)0.079 (2)
H4B0.69910.13150.29030.095*
C5B0.6161 (5)0.1683 (6)0.23212 (19)0.0637 (18)
H5B0.66450.21670.21790.076*
C6B0.5227 (5)0.1459 (5)0.21125 (16)0.0424 (14)
C7B0.4833 (4)0.1897 (5)0.16545 (15)0.0373 (13)
S1C0.39098 (11)0.07216 (13)0.04742 (4)0.0424 (4)
N2C0.3124 (3)0.0420 (4)0.02884 (13)0.0413 (11)
H2C0.34980.11010.02550.050*
N1C0.2506 (3)0.1494 (4)0.01819 (13)0.0412 (11)
H1C0.24070.22520.00690.049*
C1C0.2390 (4)0.0238 (5)0.06380 (16)0.0384 (13)
C2C0.2042 (5)0.1022 (6)0.09904 (17)0.0497 (15)
H2C10.23160.18410.10380.060*
C3C0.1262 (5)0.0529 (7)0.12699 (18)0.0594 (17)
H3C0.09990.10290.15110.071*
C4C0.0864 (5)0.0703 (7)0.11974 (19)0.0640 (18)
H4C0.03400.10030.13920.077*
C5C0.1218 (5)0.1488 (6)0.08492 (18)0.0579 (17)
H5C0.09470.23090.08010.069*
C6C0.1999 (4)0.0990 (5)0.05733 (16)0.0379 (13)
C7C0.3165 (4)0.0615 (5)0.00110 (15)0.0359 (12)
S1D0.12947 (13)0.19192 (16)0.08961 (6)0.0597 (4)
C7DA0.102 (3)0.308 (2)0.1295 (6)0.047 (2)0.510 (11)
N1DA0.0514 (12)0.4204 (14)0.1195 (4)0.051 (2)0.510 (11)
H1DA0.02510.44080.09320.062*0.510 (11)
N2DA0.1402 (16)0.3218 (16)0.1726 (6)0.050 (2)0.510 (11)
H2DA0.18170.26820.18610.060*0.510 (11)
C1DA0.0483 (11)0.4972 (13)0.1579 (4)0.058 (2)0.510 (11)
C2DA0.0083 (12)0.6206 (13)0.1639 (4)0.072 (3)0.510 (11)
H2D10.02810.66430.14070.086*0.510 (11)
C3DA0.0261 (13)0.6741 (13)0.2063 (4)0.077 (3)0.510 (11)
H3DA0.00100.75570.21190.092*0.510 (11)
C4DA0.0813 (12)0.6137 (14)0.2405 (4)0.073 (3)0.510 (11)
H4DA0.09130.65490.26840.088*0.510 (11)
C5DA0.1230 (12)0.4907 (13)0.2342 (4)0.066 (3)0.510 (11)
H5DA0.16160.44930.25710.079*0.510 (11)
C6DA0.1042 (16)0.4323 (16)0.1918 (5)0.058 (2)0.510 (11)
C7DB0.100 (3)0.308 (2)0.1246 (6)0.047 (2)0.490 (11)
N1DB0.0302 (13)0.4050 (16)0.1180 (5)0.052 (2)0.490 (11)
H1DB0.00410.41960.09290.063*0.490 (11)
N2DB0.1267 (17)0.3107 (17)0.1694 (6)0.050 (2)0.490 (11)
H2DB0.16420.25320.18320.060*0.490 (11)
C1DB0.0226 (13)0.4761 (14)0.1574 (4)0.057 (2)0.490 (11)
C2DB0.0402 (12)0.5793 (14)0.1674 (4)0.068 (3)0.490 (11)
H2D20.08560.61560.14580.081*0.490 (11)
C3DB0.0308 (13)0.6243 (15)0.2113 (4)0.076 (3)0.490 (11)
H3DB0.06740.69780.21870.092*0.490 (11)
C4DB0.0294 (13)0.5667 (15)0.2445 (4)0.073 (3)0.490 (11)
H4DB0.03080.59940.27380.088*0.490 (11)
C5DB0.0890 (12)0.4592 (14)0.2348 (5)0.066 (3)0.490 (11)
H5DB0.12900.41780.25730.079*0.490 (11)
C6DB0.0861 (16)0.4164 (16)0.1898 (5)0.057 (2)0.490 (11)
S1E0.56575 (11)0.32525 (13)0.00676 (4)0.0403 (3)
N2E0.5058 (4)0.2104 (4)0.07191 (15)0.0589 (15)
H2E0.54860.14790.06810.071*
N1E0.4215 (3)0.3827 (4)0.06072 (13)0.0421 (11)
H1E0.39980.45200.04810.051*
C1E0.4390 (5)0.2242 (5)0.10927 (17)0.0497 (15)
C2E0.4218 (6)0.1484 (7)0.1478 (2)0.083 (2)
H2E10.45800.07230.15220.100*
C3E0.3491 (6)0.1912 (7)0.1789 (2)0.075 (2)
H3E0.33660.14400.20550.090*
C4E0.2947 (5)0.3003 (7)0.17208 (19)0.0642 (19)
H4E0.24460.32440.19370.077*
C5E0.3113 (5)0.3769 (6)0.13401 (17)0.0547 (16)
H5E0.27470.45280.12980.066*
C6E0.3845 (4)0.3350 (5)0.10271 (16)0.0395 (13)
C7E0.4946 (4)0.3067 (5)0.04294 (15)0.0347 (12)
C3A0.1140 (5)0.8624 (5)0.0417 (2)0.0516 (15)
H3A0.08120.94240.03980.062*
C4A0.1721 (5)0.8318 (5)0.0802 (2)0.0520 (15)
H4A0.17880.89190.10370.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0511 (5)0.0576 (5)0.0300 (4)0.0079 (4)0.0013 (3)0.0036 (3)
Cu20.0444 (4)0.0630 (5)0.0349 (4)0.0075 (4)0.0048 (3)0.0015 (3)
S2A0.0462 (9)0.0366 (7)0.0326 (7)0.0106 (7)0.0072 (6)0.0045 (6)
S1A0.0516 (9)0.0402 (8)0.0292 (7)0.0107 (7)0.0076 (6)0.0043 (6)
N1A0.042 (3)0.033 (2)0.032 (2)0.005 (2)0.0018 (19)0.0042 (18)
O2A0.079 (3)0.057 (3)0.029 (2)0.012 (2)0.0069 (19)0.0065 (17)
O1A0.054 (3)0.044 (2)0.052 (2)0.006 (2)0.0172 (19)0.0119 (18)
C1A0.034 (3)0.033 (3)0.036 (3)0.004 (2)0.001 (2)0.004 (2)
C2A0.046 (4)0.036 (3)0.046 (3)0.006 (3)0.001 (3)0.001 (2)
C5A0.049 (4)0.043 (3)0.032 (3)0.006 (3)0.001 (2)0.009 (2)
C6A0.034 (3)0.031 (3)0.032 (3)0.005 (2)0.003 (2)0.003 (2)
C7A0.039 (3)0.030 (3)0.030 (3)0.002 (2)0.002 (2)0.000 (2)
S2B0.0504 (9)0.0579 (10)0.0370 (8)0.0114 (8)0.0008 (7)0.0149 (7)
O1B0.084 (4)0.056 (3)0.077 (3)0.006 (3)0.014 (3)0.013 (2)
O2B0.061 (3)0.099 (3)0.041 (2)0.033 (3)0.010 (2)0.025 (2)
S1B0.0454 (9)0.0625 (10)0.0317 (7)0.0035 (8)0.0042 (6)0.0049 (7)
N1B0.047 (3)0.041 (3)0.025 (2)0.008 (2)0.0028 (19)0.0046 (18)
C1B0.056 (4)0.047 (3)0.027 (3)0.019 (3)0.003 (3)0.005 (2)
C2B0.089 (6)0.064 (4)0.045 (4)0.016 (4)0.000 (3)0.016 (3)
C3B0.106 (7)0.086 (5)0.039 (4)0.013 (5)0.020 (4)0.012 (4)
C4B0.089 (6)0.085 (5)0.059 (4)0.005 (5)0.041 (4)0.010 (4)
C5B0.072 (5)0.070 (4)0.047 (4)0.001 (4)0.020 (3)0.009 (3)
C6B0.055 (4)0.047 (3)0.024 (3)0.013 (3)0.009 (2)0.006 (2)
C7B0.047 (3)0.038 (3)0.025 (3)0.010 (3)0.009 (2)0.003 (2)
S1C0.0527 (9)0.0340 (7)0.0393 (8)0.0090 (7)0.0090 (6)0.0062 (6)
N2C0.044 (3)0.035 (3)0.044 (3)0.010 (2)0.002 (2)0.008 (2)
N1C0.052 (3)0.033 (2)0.037 (2)0.013 (2)0.007 (2)0.0055 (19)
C1C0.042 (3)0.040 (3)0.033 (3)0.000 (3)0.004 (2)0.002 (2)
C2C0.059 (4)0.045 (3)0.045 (3)0.005 (3)0.004 (3)0.010 (3)
C3C0.065 (5)0.074 (5)0.039 (3)0.008 (4)0.005 (3)0.014 (3)
C4C0.068 (5)0.076 (5)0.045 (4)0.008 (4)0.022 (3)0.002 (3)
C5C0.064 (4)0.059 (4)0.049 (4)0.019 (4)0.011 (3)0.003 (3)
C6C0.040 (3)0.040 (3)0.035 (3)0.005 (3)0.003 (2)0.000 (2)
C7C0.045 (3)0.032 (3)0.032 (3)0.000 (3)0.004 (2)0.006 (2)
S1D0.0449 (10)0.0576 (10)0.0747 (11)0.0057 (8)0.0136 (8)0.0153 (8)
C7DA0.045 (4)0.051 (4)0.044 (4)0.007 (4)0.004 (4)0.000 (4)
N1DA0.052 (5)0.056 (4)0.045 (4)0.014 (4)0.007 (4)0.002 (4)
N2DA0.050 (5)0.058 (4)0.042 (4)0.014 (4)0.008 (4)0.003 (4)
C1DA0.060 (5)0.064 (4)0.050 (4)0.022 (4)0.006 (4)0.000 (4)
C2DA0.076 (6)0.073 (5)0.065 (4)0.025 (5)0.006 (5)0.005 (4)
C3DA0.083 (6)0.077 (6)0.069 (5)0.021 (5)0.002 (5)0.012 (5)
C4DA0.076 (6)0.081 (6)0.062 (4)0.016 (5)0.002 (5)0.008 (5)
C5DA0.068 (6)0.079 (5)0.050 (4)0.015 (5)0.005 (5)0.002 (4)
C6DA0.060 (5)0.066 (4)0.046 (4)0.016 (4)0.008 (4)0.000 (4)
C7DB0.045 (4)0.052 (4)0.043 (4)0.006 (4)0.006 (4)0.001 (4)
N1DB0.052 (5)0.057 (4)0.046 (4)0.015 (4)0.011 (4)0.001 (4)
N2DB0.049 (5)0.056 (4)0.044 (4)0.016 (4)0.007 (4)0.004 (4)
C1DB0.058 (5)0.063 (4)0.049 (4)0.020 (4)0.007 (4)0.001 (4)
C2DB0.069 (6)0.071 (5)0.061 (4)0.023 (5)0.005 (5)0.005 (4)
C3DB0.078 (6)0.081 (6)0.070 (5)0.028 (5)0.001 (5)0.012 (5)
C4DB0.078 (6)0.083 (6)0.059 (4)0.018 (5)0.006 (5)0.011 (5)
C5DB0.068 (6)0.078 (5)0.051 (4)0.012 (5)0.008 (5)0.002 (4)
C6DB0.059 (5)0.066 (4)0.046 (4)0.014 (4)0.007 (4)0.001 (4)
S1E0.0499 (9)0.0381 (8)0.0330 (7)0.0048 (7)0.0039 (6)0.0018 (6)
N2E0.083 (4)0.044 (3)0.049 (3)0.028 (3)0.011 (3)0.014 (2)
N1E0.056 (3)0.037 (3)0.034 (2)0.016 (2)0.006 (2)0.0056 (19)
C1E0.072 (4)0.041 (3)0.036 (3)0.013 (3)0.005 (3)0.007 (3)
C2E0.102 (6)0.064 (5)0.079 (5)0.030 (5)0.027 (4)0.037 (4)
C3E0.101 (6)0.075 (5)0.047 (4)0.019 (5)0.016 (4)0.027 (3)
C4E0.067 (5)0.087 (5)0.038 (3)0.013 (4)0.005 (3)0.011 (3)
C5E0.064 (4)0.062 (4)0.039 (3)0.024 (4)0.004 (3)0.005 (3)
C6E0.052 (4)0.039 (3)0.027 (3)0.002 (3)0.006 (2)0.003 (2)
C7E0.045 (3)0.029 (3)0.031 (3)0.003 (3)0.008 (2)0.004 (2)
C3A0.056 (4)0.029 (3)0.070 (4)0.008 (3)0.006 (3)0.009 (3)
C4A0.057 (4)0.043 (3)0.057 (4)0.005 (3)0.003 (3)0.020 (3)
Geometric parameters (Å, º) top
Cu1—S1E2.2748 (16)C5C—H5C0.9300
Cu1—S1B2.3057 (17)S1D—C7DB1.643 (11)
Cu1—S1A2.3261 (15)S1D—C7DA1.728 (10)
Cu1—S1C2.4795 (15)C7DA—N2DA1.349 (8)
Cu1—Cu22.6068 (11)C7DA—N1DA1.362 (9)
Cu2—N1B2.047 (4)N1DA—C1DA1.384 (8)
Cu2—S1D2.2532 (18)N1DA—H1DA0.8600
Cu2—S1C2.3391 (16)N2DA—C6DA1.367 (7)
Cu2—S1A2.5470 (16)N2DA—H2DA0.8600
S2A—O1A1.433 (4)C1DA—C6DA1.382 (8)
S2A—O2A1.440 (4)C1DA—C2DA1.389 (10)
S2A—N1A1.651 (4)C2DA—C3DA1.376 (10)
S2A—C1A1.754 (5)C2DA—H2D10.9300
S1A—C7A1.690 (5)C3DA—C4DA1.364 (10)
N1A—C7A1.324 (6)C3DA—H3DA0.9300
C1A—C2A1.374 (7)C4DA—C5DA1.395 (10)
C1A—C6A1.389 (6)C4DA—H4DA0.9300
C2A—C3A1.384 (7)C5DA—C6DA1.399 (9)
C2A—H2A0.9300C5DA—H5DA0.9300
C5A—C6A1.376 (6)C7DB—N2DB1.349 (8)
C5A—C4A1.381 (7)C7DB—N1DB1.363 (9)
C5A—H5A0.9300N1DB—C1DB1.383 (8)
C6A—C7A1.496 (6)N1DB—H1DB0.8600
S2B—O1B1.436 (4)N2DB—C6DB1.367 (7)
S2B—O2B1.442 (4)N2DB—H2DB0.8600
S2B—N1B1.659 (4)C1DB—C6DB1.382 (8)
S2B—C1B1.759 (6)C1DB—C2DB1.389 (10)
S1B—C7B1.674 (6)C2DB—C3DB1.376 (10)
N1B—C7B1.326 (7)C2DB—H2D20.9300
C1B—C6B1.361 (8)C3DB—C4DB1.364 (10)
C1B—C2B1.379 (7)C3DB—H3DB0.9300
C2B—C3B1.378 (10)C4DB—C5DB1.395 (10)
C2B—H2B0.9300C4DB—H4DB0.9300
C3B—C4B1.370 (10)C5DB—C6DB1.399 (9)
C3B—H3B0.9300C5DB—H5DB0.9300
C4B—C5B1.400 (8)S1E—C7E1.711 (5)
C4B—H4B0.9300N2E—C7E1.321 (6)
C5B—C6B1.370 (8)N2E—C1E1.383 (7)
C5B—H5B0.9300N2E—H2E0.8600
C6B—C7B1.493 (6)N1E—C7E1.330 (6)
S1C—C7C1.698 (5)N1E—C6E1.397 (6)
N2C—C7C1.342 (6)N1E—H1E0.8600
N2C—C1C1.391 (6)C1E—C6E1.367 (7)
N2C—H2C0.8600C1E—C2E1.388 (8)
N1C—C7C1.336 (6)C2E—C3E1.367 (9)
N1C—C6C1.403 (6)C2E—H2E10.9300
N1C—H1C0.8600C3E—C4E1.353 (8)
C1C—C2C1.376 (7)C3E—H3E0.9300
C1C—C6C1.381 (7)C4E—C5E1.380 (8)
C2C—C3C1.382 (8)C4E—H4E0.9300
C2C—H2C10.9300C5E—C6E1.372 (7)
C3C—C4C1.392 (8)C5E—H5E0.9300
C3C—H3C0.9300C3A—C4A1.374 (7)
C4C—C5C1.370 (8)C3A—H3A0.9300
C4C—H4C0.9300C4A—H4A0.9300
C5C—C6C1.380 (7)
S1E—Cu1—S1B107.65 (6)C6C—C5C—H5C122.0
S1E—Cu1—S1A127.45 (6)C5C—C6C—C1C122.1 (5)
S1B—Cu1—S1A100.35 (6)C5C—C6C—N1C131.2 (5)
S1E—Cu1—S1C103.00 (5)C1C—C6C—N1C106.5 (4)
S1B—Cu1—S1C104.24 (6)N1C—C7C—N2C107.5 (4)
S1A—Cu1—S1C112.06 (6)N1C—C7C—S1C127.8 (4)
S1E—Cu1—Cu2153.66 (5)N2C—C7C—S1C124.7 (4)
S1B—Cu1—Cu292.79 (5)C7DB—S1D—C7DA4.1 (12)
S1A—Cu1—Cu261.86 (4)C7DB—S1D—Cu2101.2 (14)
S1C—Cu1—Cu254.69 (4)C7DA—S1D—Cu299.4 (12)
N1B—Cu2—S1D127.84 (14)N2DA—C7DA—N1DA105.5 (7)
N1B—Cu2—S1C98.41 (13)N2DA—C7DA—S1D129.4 (10)
S1D—Cu2—S1C118.17 (6)N1DA—C7DA—S1D123.8 (9)
N1B—Cu2—S1A100.65 (12)C7DA—N1DA—C1DA110.1 (5)
S1D—Cu2—S1A100.55 (6)C7DA—N1DA—H1DA125.0
S1C—Cu2—S1A109.27 (5)C1DA—N1DA—H1DA125.0
N1B—Cu2—Cu187.97 (13)C7DA—N2DA—C6DA111.0 (5)
S1D—Cu2—Cu1141.59 (6)C7DA—N2DA—H2DA124.5
S1C—Cu2—Cu159.89 (4)C6DA—N2DA—H2DA124.5
S1A—Cu2—Cu153.64 (4)C6DA—C1DA—N1DA106.2 (6)
O1A—S2A—O2A115.1 (2)C6DA—C1DA—C2DA122.8 (7)
O1A—S2A—N1A110.7 (2)N1DA—C1DA—C2DA130.8 (6)
O2A—S2A—N1A109.6 (2)C3DA—C2DA—C1DA115.6 (7)
O1A—S2A—C1A113.0 (2)C3DA—C2DA—H2D1122.2
O2A—S2A—C1A109.8 (2)C1DA—C2DA—H2D1122.2
N1A—S2A—C1A97.1 (2)C4DA—C3DA—C2DA123.4 (8)
C7A—S1A—Cu1114.24 (17)C4DA—C3DA—H3DA118.3
C7A—S1A—Cu2109.51 (17)C2DA—C3DA—H3DA118.3
Cu1—S1A—Cu264.49 (4)C3DA—C4DA—C5DA120.8 (8)
C7A—N1A—S2A110.0 (3)C3DA—C4DA—H4DA119.6
C2A—C1A—C6A122.6 (4)C5DA—C4DA—H4DA119.6
C2A—C1A—S2A130.6 (4)C4DA—C5DA—C6DA117.2 (7)
C6A—C1A—S2A106.5 (4)C4DA—C5DA—H5DA121.4
C1A—C2A—C3A117.3 (5)C6DA—C5DA—H5DA121.4
C1A—C2A—H2A121.4N2DA—C6DA—C1DA106.6 (5)
C3A—C2A—H2A121.4N2DA—C6DA—C5DA132.7 (6)
C6A—C5A—C4A118.9 (5)C1DA—C6DA—C5DA120.2 (7)
C6A—C5A—H5A120.5N2DB—C7DB—N1DB105.5 (7)
C4A—C5A—H5A120.5N2DB—C7DB—S1D124.8 (10)
C5A—C6A—C1A119.2 (5)N1DB—C7DB—S1D128.5 (12)
C5A—C6A—C7A129.8 (4)C7DB—N1DB—C1DB110.1 (5)
C1A—C6A—C7A111.0 (4)C7DB—N1DB—H1DB125.0
N1A—C7A—C6A114.9 (4)C1DB—N1DB—H1DB125.0
N1A—C7A—S1A125.5 (4)C7DB—N2DB—C6DB111.0 (5)
C6A—C7A—S1A119.5 (3)C7DB—N2DB—H2DB124.5
O1B—S2B—O2B116.8 (3)C6DB—N2DB—H2DB124.5
O1B—S2B—N1B110.3 (2)C6DB—C1DB—N1DB106.2 (6)
O2B—S2B—N1B109.1 (2)C6DB—C1DB—C2DB122.7 (7)
O1B—S2B—C1B112.5 (3)N1DB—C1DB—C2DB130.8 (6)
O2B—S2B—C1B110.7 (2)C3DB—C2DB—C1DB115.6 (7)
N1B—S2B—C1B95.3 (3)C3DB—C2DB—H2D2122.2
C7B—S1B—Cu1105.60 (19)C1DB—C2DB—H2D2122.2
C7B—N1B—S2B111.5 (3)C4DB—C3DB—C2DB123.4 (8)
C7B—N1B—Cu2128.4 (3)C4DB—C3DB—H3DB118.3
S2B—N1B—Cu2120.0 (3)C2DB—C3DB—H3DB118.3
C6B—C1B—C2B122.9 (6)C3DB—C4DB—C5DB120.8 (8)
C6B—C1B—S2B107.9 (4)C3DB—C4DB—H4DB119.6
C2B—C1B—S2B129.3 (5)C5DB—C4DB—H4DB119.6
C3B—C2B—C1B117.6 (7)C4DB—C5DB—C6DB117.2 (7)
C3B—C2B—H2B121.2C4DB—C5DB—H5DB121.4
C1B—C2B—H2B121.2C6DB—C5DB—H5DB121.4
C4B—C3B—C2B120.2 (6)N2DB—C6DB—C1DB106.6 (5)
C4B—C3B—H3B119.9N2DB—C6DB—C5DB132.8 (6)
C2B—C3B—H3B119.9C1DB—C6DB—C5DB120.2 (7)
C3B—C4B—C5B121.3 (7)C7E—S1E—Cu1106.33 (18)
C3B—C4B—H4B119.3C7E—N2E—C1E110.5 (5)
C5B—C4B—H4B119.3C7E—N2E—H2E124.7
C6B—C5B—C4B118.1 (7)C1E—N2E—H2E124.7
C6B—C5B—H5B121.0C7E—N1E—C6E110.9 (4)
C4B—C5B—H5B121.0C7E—N1E—H1E124.6
C1B—C6B—C5B119.9 (5)C6E—N1E—H1E124.6
C1B—C6B—C7B111.9 (5)C6E—C1E—N2E107.0 (4)
C5B—C6B—C7B128.2 (6)C6E—C1E—C2E121.3 (6)
N1B—C7B—C6B113.3 (5)N2E—C1E—C2E131.8 (6)
N1B—C7B—S1B124.9 (4)C3E—C2E—C1E116.7 (6)
C6B—C7B—S1B121.8 (4)C3E—C2E—H2E1121.6
C7C—S1C—Cu2106.24 (18)C1E—C2E—H2E1121.6
C7C—S1C—Cu1114.12 (18)C4E—C3E—C2E121.8 (6)
Cu2—S1C—Cu165.43 (4)C4E—C3E—H3E119.1
C7C—N2C—C1C110.5 (4)C2E—C3E—H3E119.1
C7C—N2C—H2C124.7C3E—C4E—C5E122.2 (6)
C1C—N2C—H2C124.7C3E—C4E—H4E118.9
C7C—N1C—C6C109.6 (4)C5E—C4E—H4E118.9
C7C—N1C—H1C125.2C6E—C5E—C4E116.4 (6)
C6C—N1C—H1C125.2C6E—C5E—H5E121.8
C2C—C1C—C6C121.8 (5)C4E—C5E—H5E121.8
C2C—C1C—N2C132.4 (5)C1E—C6E—C5E121.7 (5)
C6C—C1C—N2C105.8 (4)C1E—C6E—N1E104.8 (5)
C1C—C2C—C3C116.5 (5)C5E—C6E—N1E133.5 (5)
C1C—C2C—H2C1121.8N2E—C7E—N1E106.8 (4)
C3C—C2C—H2C1121.8N2E—C7E—S1E124.3 (4)
C2C—C3C—C4C121.2 (5)N1E—C7E—S1E128.9 (4)
C2C—C3C—H3C119.4C4A—C3A—C2A120.9 (5)
C4C—C3C—H3C119.4C4A—C3A—H3A119.5
C5C—C4C—C3C122.3 (6)C2A—C3A—H3A119.5
C5C—C4C—H4C118.8C3A—C4A—C5A121.1 (5)
C3C—C4C—H4C118.8C3A—C4A—H4A119.4
C4C—C5C—C6C116.1 (6)C5A—C4A—H4A119.4
C4C—C5C—H5C122.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1DA—H1DA···O1Ai0.862.132.957 (14)161
N1C—H1C···N1A0.862.173.014 (6)166
N2DA—H2DA···O2B0.861.902.756 (19)174
N2DB—H2DB···O2B0.861.972.827 (12)173
Symmetry code: (i) x, y+1, z.

Experimental details

(I)(II)
Crystal data
Chemical formula[Cu2(C7H4NO2S2)2(C7H6N2S)2(C2H3N)][Cu2(C7H4NO2S2)2(C7H6N2S)3]
Mr865.01974.14
Crystal system, space groupTriclinic, P1Monoclinic, P21/c
Temperature (K)293293
a, b, c (Å)8.0466 (1), 13.8150 (2), 15.3621 (2)13.2395 (12), 10.2731 (10), 29.536 (15)
α, β, γ (°)87.739 (1), 89.480 (1), 79.033 (1)90, 93.135 (16), 90
V3)1675.21 (4)4011 (2)
Z24
Radiation typeMo KαMo Kα
µ (mm1)1.691.48
Crystal size (mm)0.30 × 0.20 × 0.100.25 × 0.15 × 0.10
Data collection
DiffractometerOxford Xcalibur Eos Gemini
diffractometer
Oxford Xcalibur Eos Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.716, 0.8010.814, 0.867
No. of measured, independent and
observed [I > 2σ(I)] reflections
97442, 8285, 5570 18885, 8812, 4863
Rint0.0460.066
(sin θ/λ)max1)0.6840.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.118, 1.10 0.067, 0.154, 1.01
No. of reflections82858812
No. of parameters443587
No. of restraints0317
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.650.78, 0.39

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury [Version 1.4.2 (Build 2); Macrae et al., 2008], PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1D—H1DA···O1Ai0.862.002.841 (4)167
N1C—H1C···N1A0.862.102.918 (4)160
N2D—H2DA···O1B0.862.052.893 (4)166
Symmetry code: (i) x+1, y+1, z.
Least-squares planes, deviations, and angles between the planes for [Cu2(tsac)2(Sbim)2(CH3CN)], (I) top
Planer.m.s.tsac(A)tsac(B)Sbim(C)
tsac(A)0.0159
tsac(B)0.017186.89 (5)
Sbim(C)0.041414.68 (8)89.73 (7)
Sbim(D)0.013884.99 (8)23.30 (8)86.27 (9)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1DA—H1DA···O1Ai0.862.132.957 (14)161
N1C—H1C···N1A0.862.173.014 (6)166
N2DA—H2DA···O2B0.861.902.756 (19)174
N2DB—H2DB···O2B0.861.972.827 (12)173
Symmetry code: (i) x, y+1, z.
Least-squares planes, deviations, and angles between the planes for [Cu2(tsac)2(Sbim)3], (II) top
Planer.m.s.tsac(A)tsac(B)Sbim(C)Sbim(DA)
tsac(A)0.0317
tsac(B)0.036284.40 (8)
Sbim(C)0.044811.33 (17)81.95 (11)
Sbim(DA)0.049506.9 (5)88.6 (3)17.8 (5)
Sbim(E)0.009710.6 (2)88.89 (12)09.6 (2)13.9 (5)
 

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