In the mononuclear complex title salt, all of the non-H atoms of the cation lie on a mirror plane, as do the N and one O atom of the nitrate anion, such that the planes of the cation and anion are mutually orthogonal. In the crystal, layers parallel to (010) are generated by N—H⋯O hydrogen bonds, supported by short S⋯O [3.196 (4) and 3.038 (3) Å] and S⋯S contacts [3.4392 (13) Å].
Keywords: copper(II) complex; 1,3-thiazolidine-2-thione; 3-(2-thiazolin-2-yl)thiazolidine-2-thione; crystal structure
Abstract
The mononuclear complex salt, [Cu(C3H5NS2)(C6H8N2S3)]NO3, contains a [C9H13CuN3S5]+ cation and an NO3 − anion. All of the non-H atoms of the cation lie on a mirror plane, as do the N and one O atom of the nitrate anion, such that the planes of the cation and anion are mutually orthogonal. The cationic complex adopts a slightly distorted trigonal–planar geometry about the CuI cation. In the crystal, layers parallel to (010) are generated by N—H⋯O hydrogen bonds, supported by short S⋯O [3.196 (4) and 3.038 (3) Å] and S⋯S contacts [3.4392 (13) Å]. Adjacent layers are linked by C—H⋯O hydrogen bonds and weak π–π stacking interactions [centroid–centroid distance = 4.0045 (10) Å] between the thiazoline rings, forming a three-dimensional network. This stacking also imposes a close contact, of approximately 3.678 Å, between the CuI cations and the centroids of the six-membered chelate rings of molecules in adjacent layers.
Chemical context
1,3-Thiazolidine-2-thione (tzdSH: C3H5NS2), is a well known heterocyclic thione/thiol ligand. Crystallographic studies and investigations of its modes of coordination have been reported (Raper et al., 1998 ▶; Ainscough et al., 1985 ▶; Kubiak & Głowiak, 1987 ▶; Cowie & Sielisch, 1988 ▶; Ballester et al., 1992 ▶; Fackler et al., 1992 ▶; Saithong et al., 2007 ▶). We are interested in the coordination behaviour and structure of tzdSH complexes with CuII cations. We have normally used Cu(NO3)2·3H2O as the starting material with the possibility that the NO3
− anions could function as simple counter-ions to balance the charge on the metal or alternatively act as a ligand to the metal ion (Ferrer et al., 2000 ▶; Pal et al., 2005 ▶; Khavasi et al., 2011 ▶). However, the tzdSH ligand could also act as a reducing agent during the reaction, converting CuII to CuI and forming 3-(2-thiazolin-2-yl)thiazolidine-2-thione [tztzdt or C6H8N2S3] in the process. A similar reduction reaction was described previously by Ainscough et al. (1985 ▶). Complexation of the resulting CuI cation to both the tztzdt ligand thus formed, and to tzdSH generates the title compound.
Structural commentary
The title compound is a mononuclear CuI complex and its structure is shown in Fig. 1 ▶. The CuI atom has a distorted trigonal–planar coordination geometry and is chelated by the exocyclic S3 atom and the N3 atom of the thiazolidine ring of the tztzdt ligand, forming a six-membered chelate ring. The trigonal coordination sphere is completed by the exocyclic S1 atom of the tzdSH ligand. The NO3 − acts solely as counter-ion. The complex molecule is strictly planar as all non-hydrogen atoms of the complex lie on a mirror plane. Atoms N4 and O1 of the nitrate counter-ion also lie on a mirror plane, such that the mirror plane of the cationic complex is perpendicular to that of the NO3 − anion. The Cu1—S1 [2.1774 (9) Å], and Cu1—N3 [1.956 (3) Å] bond lengths are not unusual in comparison with the mean values [Cu—S = 2.21 (3) and Cu—N = 1.99 (3) Å] found in the Cambridge Structural Database. In contrast, the Cu1—S1 distance of 2.1774 (9) Å is somewhat shorter than those previously reported for other CuI complexes of tzdSH [mean Cu—S = 2.33 (1) Å].
Figure 1.
Molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (i) x, −y + ½, z.]
Supramolecular features
In the crystal, layers are generated parallel to (010) by classical N1—H1⋯O1 hydrogen bonds (Table 1 ▶) supported by short S2⋯O2 [3.038 (3) Å], S5⋯O2 [3.196 (4) Å] and S1⋯S4 [3.4392 (13) Å] contacts (Fig. 2 ▶). Adjacent layers are linked by C5—H5A⋯O1 hydrogen bonds and weak π–π stacking interactions [centroid–centroid distance 4.0045 (10) Å] between the thiazoline rings of a tzdSH ligand with those of tztzdt ligands in adjacent layers, forming a three-dimensional network. This stacking also imposes a close contact, of approximately 3.678 Å, between the copper cations and the centroids of the six-membered Cu1, S3, C4, N2, C7, N3 chelate rings of the molecules in the adjacent layers (Fig. 3 ▶). The three-dimensional network of stacked layers is shown in Fig. 4 ▶.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1⋯O1i | 0.84 (2) | 2.25 (2) | 2.981 (4) | 146 (2) |
| N1—H1⋯O1ii | 0.84 (2) | 2.25 (2) | 2.981 (4) | 146 (2) |
| C5—H5A⋯O1iii | 0.97 | 2.62 | 3.388 (4) | 136 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Figure 2.
Two-dimensional sheets of molecules parallel to (010). Hydrogen bonds are drawn as dashed lines and H atoms not involved in hydrogen bonding have been omitted for clarity.
Figure 3.
π–π stacking interactions between molecules. Centroid–centroid and unusual Cu1–centroid contacts are drawn as dotted lines with the centroids shown as coloured spheres. Hydrogen bonds are drawn as dashed lines and H atoms not involved in hydrogen bonding have been omitted for clarity.
Figure 4.
The overall packing of the title compound. Hydrogen bonds are drawn as dashed lines and H atoms not involved in hydrogen bonding have been omitted for clarity.
Database survey
Only four discrete reports are given of transition-metal complexes with the metal atom chelated by the tztzdt ligand. All are copper complexes, three of CuI (Lobana et al., 2013 ▶) and the fourth a CuII coordination polymer (Ainscough et al., 1985 ▶). Complexes of tzdSH are more plentiful with 29 unique entries, ten of which involve CuI cations (see, for example: Lobana et al., 2013 ▶; Raper et al., 1998 ▶).
Synthesis and crystallization
1,3-Thiazolidine-2-thione (0.1 g, 0.084 mmol) was added to a solution of Cu(NO3)2·3H2O (0.07 g, 0.039 mmol) in an MeOH: EtOH solvent mixture (1/1 v/v) at 340 K. The mixture was refluxed for 5 h. Rod-like yellow crystals appeared after the light-brown filtrate had been kept at room temperature for a day (yield 10%). The crystals melt and decompose at 434–436 K.
Refinement
The N1—H1 hydrogen atom was located in a difference map and its coordinates were refined with U iso(H) = 1.2U eq(N). The hydrogen atoms of the methylene groups were positioned geometrically and allowed to ride on their parent atoms, with d(C—H) = 0.97 Å and U iso = 1.2U eq(C). Experimental details are given in Table 2 ▶.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | [Cu(C3H5NS2)(C6H8N2S3)]NO3 |
| M r | 449.13 |
| Crystal system, space group | Monoclinic, P21/m |
| Temperature (K) | 293 |
| a, b, c (Å) | 9.8937 (6), 6.9932 (5), 11.8054 (7) |
| β (°) | 102.078 (1) |
| V (Å3) | 798.72 (9) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 2.04 |
| Crystal size (mm) | 0.35 × 0.12 × 0.06 |
| Data collection | |
| Diffractometer | Bruker APEX CCD area detector |
| Absorption correction | Multi-scan (SADABS; Bruker, 2003 ▶) |
| T min, T max | 0.814, 1.000 |
| No. of measured, independent and observed [I > 2s(I)] reflections | 8700, 1534, 1402 |
| R int | 0.026 |
| (sin θ/λ)max (Å−1) | 0.595 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.029, 0.080, 1.07 |
| No. of reflections | 1534 |
| No. of parameters | 133 |
| No. of restraints | 1 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.37, −0.27 |
Supplementary Material
Crystal structure: contains datablock(s) I, pk030-p21-m. DOI: 10.1107/S160053681401544X/sj5420sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401544X/sj5420Isup2.hkl
CCDC reference: 1011568
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
We are grateful to the Center of Excellence for Innovation in Chemistry (PERCH–CIC), Office of the Higher Education Commission, Ministry of Education, and the Department of Chemistry, Faculty of Science, Prince of Songkla University, for financial support. We also thank Professor Dr Brian Hodgson, Faculty of Science, Prince of Songkla University, for reading the manuscript and providing valuable comments.
supplementary crystallographic information
Crystal data
| [Cu(C3H5NS2)(C6H8N2S3)]NO3 | F(000) = 456 |
| Mr = 449.13 | Dx = 1.867 Mg m−3 |
| Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yb | Cell parameters from 3943 reflections |
| a = 9.8937 (6) Å | θ = 2.5–28.0° |
| b = 6.9932 (5) Å | µ = 2.04 mm−1 |
| c = 11.8054 (7) Å | T = 293 K |
| β = 102.078 (1)° | Block, yellow |
| V = 798.72 (9) Å3 | 0.35 × 0.12 × 0.06 mm |
| Z = 2 |
Data collection
| Bruker APEX CCD area-detector diffractometer | 1534 independent reflections |
| Radiation source: fine-focus sealed tube | 1402 reflections with I > 2s(I) |
| Graphite monochromator | Rint = 0.026 |
| Frames, each covering 0.3 ° in ω scans | θmax = 25.0°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −11→11 |
| Tmin = 0.814, Tmax = 1.000 | k = −8→8 |
| 8700 measured reflections | l = −14→14 |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0471P)2 + 0.3435P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max = 0.001 |
| 1534 reflections | Δρmax = 0.37 e Å−3 |
| 133 parameters | Δρmin = −0.27 e Å−3 |
| 1 restraint | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0074 (13) |
Special details
| 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 al data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Cu1 | 0.53707 (4) | 0.2500 | 0.52014 (4) | 0.05377 (19) | |
| S1 | 0.75417 (8) | 0.2500 | 0.60684 (7) | 0.0471 (2) | |
| S2 | 0.61224 (9) | 0.2500 | 0.80799 (8) | 0.0494 (2) | |
| S3 | 0.34723 (10) | 0.2500 | 0.58878 (8) | 0.0641 (3) | |
| S4 | 0.05567 (9) | 0.2500 | 0.50537 (9) | 0.0571 (3) | |
| S5 | 0.28736 (10) | 0.2500 | 0.15159 (7) | 0.0527 (3) | |
| N1 | 0.8731 (3) | 0.2500 | 0.8311 (3) | 0.0509 (7) | |
| H1 | 0.951 (3) | 0.2500 | 0.813 (3) | 0.061* | |
| N2 | 0.2147 (3) | 0.2500 | 0.3586 (2) | 0.0404 (6) | |
| N3 | 0.4543 (3) | 0.2500 | 0.3544 (2) | 0.0446 (6) | |
| C1 | 0.7591 (3) | 0.2500 | 0.7514 (3) | 0.0408 (7) | |
| C2 | 0.7099 (4) | 0.2500 | 0.9567 (3) | 0.0565 (9) | |
| H2A | 0.6879 | 0.3626 | 0.9973 | 0.068* | 0.50 |
| H2B | 0.6879 | 0.1374 | 0.9973 | 0.068* | 0.50 |
| C3 | 0.8615 (4) | 0.2500 | 0.9509 (3) | 0.0654 (11) | |
| H3A | 0.9066 | 0.3624 | 0.9897 | 0.079* | 0.50 |
| H3B | 0.9066 | 0.1376 | 0.9897 | 0.079* | 0.50 |
| C4 | 0.2171 (3) | 0.2500 | 0.4737 (3) | 0.0434 (7) | |
| C5 | −0.0321 (4) | 0.2500 | 0.3563 (4) | 0.0737 (12) | |
| H5A | −0.0901 | 0.1375 | 0.3396 | 0.088* | 0.50 |
| H5B | −0.0901 | 0.3625 | 0.3396 | 0.088* | 0.50 |
| C6 | 0.0736 (3) | 0.2500 | 0.2847 (3) | 0.0592 (10) | |
| H6A | 0.0618 | 0.3623 | 0.2354 | 0.071* | 0.50 |
| H6B | 0.0618 | 0.1377 | 0.2354 | 0.071* | 0.50 |
| C7 | 0.3273 (3) | 0.2500 | 0.3040 (3) | 0.0392 (7) | |
| C8 | 0.4694 (4) | 0.2500 | 0.1485 (3) | 0.0577 (9) | |
| H8A | 0.4926 | 0.1374 | 0.1085 | 0.069* | 0.50 |
| H8B | 0.4926 | 0.3626 | 0.1085 | 0.069* | 0.50 |
| C9 | 0.5473 (4) | 0.2500 | 0.2725 (3) | 0.0542 (9) | |
| H9A | 0.6062 | 0.1379 | 0.2861 | 0.065* | 0.50 |
| H9B | 0.6062 | 0.3621 | 0.2861 | 0.065* | 0.50 |
| N4 | 0.2237 (3) | 0.2500 | 0.8549 (2) | 0.0596 (9) | |
| O1 | 0.1564 (3) | 0.1019 (4) | 0.8343 (2) | 0.1071 (8) | |
| O2 | 0.3440 (3) | 0.2500 | 0.8948 (3) | 0.1254 (18) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cu1 | 0.0365 (3) | 0.0762 (4) | 0.0445 (3) | 0.000 | −0.00081 (18) | 0.000 |
| S1 | 0.0334 (4) | 0.0643 (5) | 0.0435 (5) | 0.000 | 0.0076 (3) | 0.000 |
| S2 | 0.0366 (4) | 0.0644 (5) | 0.0474 (5) | 0.000 | 0.0093 (4) | 0.000 |
| S3 | 0.0403 (5) | 0.1106 (8) | 0.0396 (5) | 0.000 | 0.0045 (4) | 0.000 |
| S4 | 0.0369 (5) | 0.0729 (6) | 0.0632 (6) | 0.000 | 0.0145 (4) | 0.000 |
| S5 | 0.0501 (5) | 0.0668 (6) | 0.0383 (4) | 0.000 | 0.0025 (4) | 0.000 |
| N1 | 0.0345 (15) | 0.0683 (19) | 0.0471 (16) | 0.000 | 0.0020 (12) | 0.000 |
| N2 | 0.0313 (13) | 0.0443 (14) | 0.0427 (15) | 0.000 | 0.0010 (11) | 0.000 |
| N3 | 0.0350 (14) | 0.0541 (16) | 0.0438 (15) | 0.000 | 0.0059 (11) | 0.000 |
| C1 | 0.0339 (16) | 0.0407 (16) | 0.0461 (18) | 0.000 | 0.0046 (13) | 0.000 |
| C2 | 0.060 (2) | 0.066 (2) | 0.0425 (18) | 0.000 | 0.0085 (16) | 0.000 |
| C3 | 0.053 (2) | 0.091 (3) | 0.047 (2) | 0.000 | −0.0020 (17) | 0.000 |
| C4 | 0.0358 (16) | 0.0442 (17) | 0.0495 (18) | 0.000 | 0.0076 (14) | 0.000 |
| C5 | 0.039 (2) | 0.110 (4) | 0.068 (3) | 0.000 | 0.0015 (18) | 0.000 |
| C6 | 0.0361 (18) | 0.080 (3) | 0.055 (2) | 0.000 | −0.0037 (16) | 0.000 |
| C7 | 0.0390 (17) | 0.0391 (16) | 0.0380 (16) | 0.000 | 0.0044 (13) | 0.000 |
| C8 | 0.055 (2) | 0.069 (2) | 0.052 (2) | 0.000 | 0.0168 (17) | 0.000 |
| C9 | 0.0401 (18) | 0.072 (2) | 0.052 (2) | 0.000 | 0.0131 (15) | 0.000 |
| N4 | 0.0409 (17) | 0.101 (3) | 0.0340 (15) | 0.000 | 0.0022 (12) | 0.000 |
| O1 | 0.110 (2) | 0.0932 (18) | 0.122 (2) | −0.0237 (16) | 0.0328 (17) | −0.0061 (17) |
| O2 | 0.0409 (16) | 0.273 (6) | 0.0588 (18) | 0.000 | 0.0021 (14) | 0.000 |
Geometric parameters (Å, º)
| Cu1—N3 | 1.956 (3) | C2—C3 | 1.516 (5) |
| Cu1—S1 | 2.1774 (9) | C2—H2A | 0.9700 |
| Cu1—S3 | 2.1957 (10) | C2—H2B | 0.9700 |
| S1—C1 | 1.698 (3) | C3—H3A | 0.9700 |
| S2—C1 | 1.721 (3) | C3—H3B | 0.9700 |
| S2—C2 | 1.818 (4) | C5—C6 | 1.475 (6) |
| S3—C4 | 1.665 (3) | C5—H5A | 0.9700 |
| S4—C4 | 1.715 (3) | C5—H5B | 0.9700 |
| S4—C5 | 1.792 (4) | C6—H6A | 0.9700 |
| S5—C7 | 1.760 (3) | C6—H6B | 0.9700 |
| S5—C8 | 1.810 (4) | C8—C9 | 1.505 (5) |
| N1—C1 | 1.308 (4) | C8—H8A | 0.9700 |
| N1—C3 | 1.443 (5) | C8—H8B | 0.9700 |
| N1—H1 | 0.841 (19) | C9—H9A | 0.9700 |
| N2—C4 | 1.354 (4) | C9—H9B | 0.9700 |
| N2—C7 | 1.398 (4) | N4—O2 | 1.185 (4) |
| N2—C6 | 1.483 (4) | N4—O1 | 1.228 (3) |
| N3—C7 | 1.273 (4) | N4—O1i | 1.228 (3) |
| N3—C9 | 1.468 (4) | ||
| N3—Cu1—S1 | 129.45 (8) | N2—C4—S4 | 113.4 (2) |
| N3—Cu1—S3 | 99.07 (8) | S3—C4—S4 | 114.7 (2) |
| S1—Cu1—S3 | 131.48 (4) | C6—C5—S4 | 107.9 (3) |
| C1—S1—Cu1 | 106.90 (11) | C6—C5—H5A | 110.1 |
| C1—S2—C2 | 93.06 (16) | S4—C5—H5A | 110.1 |
| C4—S3—Cu1 | 105.89 (12) | C6—C5—H5B | 110.1 |
| C4—S4—C5 | 93.88 (18) | S4—C5—H5B | 110.1 |
| C7—S5—C8 | 90.55 (16) | H5A—C5—H5B | 108.4 |
| C1—N1—C3 | 118.1 (3) | C5—C6—N2 | 110.9 (3) |
| C1—N1—H1 | 121 (3) | C5—C6—H6A | 109.5 |
| C3—N1—H1 | 121 (3) | N2—C6—H6A | 109.5 |
| C4—N2—C7 | 127.9 (3) | C5—C6—H6B | 109.5 |
| C4—N2—C6 | 114.0 (3) | N2—C6—H6B | 109.5 |
| C7—N2—C6 | 118.1 (3) | H6A—C6—H6B | 108.1 |
| C7—N3—C9 | 112.7 (3) | N3—C7—N2 | 126.0 (3) |
| C7—N3—Cu1 | 129.3 (2) | N3—C7—S5 | 117.8 (2) |
| C9—N3—Cu1 | 118.0 (2) | N2—C7—S5 | 116.2 (2) |
| N1—C1—S1 | 124.2 (3) | C9—C8—S5 | 106.8 (2) |
| N1—C1—S2 | 113.1 (2) | C9—C8—H8A | 110.4 |
| S1—C1—S2 | 122.75 (18) | S5—C8—H8A | 110.4 |
| C3—C2—S2 | 106.7 (3) | C9—C8—H8B | 110.4 |
| C3—C2—H2A | 110.4 | S5—C8—H8B | 110.4 |
| S2—C2—H2A | 110.4 | H8A—C8—H8B | 108.6 |
| C3—C2—H2B | 110.4 | N3—C9—C8 | 112.1 (3) |
| S2—C2—H2B | 110.4 | N3—C9—H9A | 109.2 |
| H2A—C2—H2B | 108.6 | C8—C9—H9A | 109.2 |
| N1—C3—C2 | 109.0 (3) | N3—C9—H9B | 109.2 |
| N1—C3—H3A | 109.9 | C8—C9—H9B | 109.2 |
| C2—C3—H3A | 109.9 | H9A—C9—H9B | 107.9 |
| N1—C3—H3B | 109.9 | O2—N4—O1 | 122.47 (18) |
| C2—C3—H3B | 109.9 | O2—N4—O1i | 122.47 (18) |
| H3A—C3—H3B | 108.3 | O1—N4—O1i | 115.0 (4) |
| N2—C4—S3 | 131.9 (3) | ||
| N3—Cu1—S1—C1 | 180.0 | Cu1—S3—C4—S4 | 180.0 |
| S3—Cu1—S1—C1 | 0.0 | C5—S4—C4—N2 | 0.0 |
| N3—Cu1—S3—C4 | 0.0 | C5—S4—C4—S3 | 180.0 |
| S1—Cu1—S3—C4 | 180.0 | C4—S4—C5—C6 | 0.0 |
| S1—Cu1—N3—C7 | 180.0 | S4—C5—C6—N2 | 0.0 |
| S3—Cu1—N3—C7 | 0.0 | C4—N2—C6—C5 | 0.0 |
| S1—Cu1—N3—C9 | 0.0 | C7—N2—C6—C5 | 180.0 |
| S3—Cu1—N3—C9 | 180.0 | C9—N3—C7—N2 | 180.0 |
| C3—N1—C1—S1 | 180.0 | Cu1—N3—C7—N2 | 0.0 |
| C3—N1—C1—S2 | 0.0 | C9—N3—C7—S5 | 0.0 |
| Cu1—S1—C1—N1 | 180.0 | Cu1—N3—C7—S5 | 180.0 |
| Cu1—S1—C1—S2 | 0.0 | C4—N2—C7—N3 | 0.0 |
| C2—S2—C1—N1 | 0.0 | C6—N2—C7—N3 | 180.0 |
| C2—S2—C1—S1 | 180.0 | C4—N2—C7—S5 | 180.0 |
| C1—S2—C2—C3 | 0.0 | C6—N2—C7—S5 | 0.0 |
| C1—N1—C3—C2 | 0.000 (1) | C8—S5—C7—N3 | 0.0 |
| S2—C2—C3—N1 | 0.000 (1) | C8—S5—C7—N2 | 180.0 |
| C7—N2—C4—S3 | 0.0 | C7—S5—C8—C9 | 0.0 |
| C6—N2—C4—S3 | 180.0 | C7—N3—C9—C8 | 0.0 |
| C7—N2—C4—S4 | 180.0 | Cu1—N3—C9—C8 | 180.0 |
| C6—N2—C4—S4 | 0.0 | S5—C8—C9—N3 | 0.0 |
| Cu1—S3—C4—N2 | 0.0 |
Symmetry code: (i) x, −y+1/2, z.
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O1ii | 0.84 (2) | 2.25 (2) | 2.981 (4) | 146 (2) |
| N1—H1···O1iii | 0.84 (2) | 2.25 (2) | 2.981 (4) | 146 (2) |
| C5—H5A···O1iv | 0.97 | 2.62 | 3.388 (4) | 136 |
Symmetry codes: (ii) x+1, y, z; (iii) x+1, −y+1/2, z; (iv) −x, −y, −z+1.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, pk030-p21-m. DOI: 10.1107/S160053681401544X/sj5420sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401544X/sj5420Isup2.hkl
CCDC reference: 1011568
Additional supporting information: crystallographic information; 3D view; checkCIF report