Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027304/dn2183sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027304/dn2183Isup2.hkl |
CCDC reference: 654715
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.012 Å
- R factor = 0.065
- wR factor = 0.199
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 10.31 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu2 - Cl2 .. 11.12 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu2 - Cl3 .. 10.45 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu3 - Cl3 .. 11.23 su
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.44 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - Cl1_a .. 8.96 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu3 - Cl2 .. 8.79 su PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (1) 1.00 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu2 (1) 0.98 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu3 (1) 0.99
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check
For general background, see: Kadooka et al. (1976a,b); Delgado et al. (2006); Bell et al. (2000). For related literature, see: Kubo et al. (1998).
2,2'-dipyridyldisuldide (0.05 g,0.012 mmol), CuCl (0.18 g 0.8 mmol), were added in a mixed solvent of dry ethanol and acetonitrile, the mixture was heated for five h under reflux during the process stirring and influx were required. The resultant was then filtered to give a pure solution which was infiltrated by diethyl ether freely in a closed vessel, a weeks later some single crystals of the size suitable for X-Ray diffraction analysis precipitated.
H atoms were placed at calculated positions and were treated as riding on their parent atoms with C—H = 0.93 Å, and Uiso(H) = 1.2 Ueq(C).
2,2'-dipyridyldisuldide possessing N-donnor and S-donnor is excellent candidates for the construction of metal complexes. Examples of crystal structure reports are copper(I) (Kadooka et al., 1976a,b; Kubo et al., 1998), copper(II) (Delgado et al., 2006), cobalt(II)(Kadooka et al., 1976b), mercury(II) (Bell et al., 2000). Recently, we obtained the title novel copper complex (I) by the reaction of cuprous chloride, 2,2'-dipyridyldisuldide in a dry ethanol and acetonitrile solution, and its crystal structure is reported here.
The asymmetric unit of the title compound is build up from one and a half dinuclear copper complexes; one of the dinuclear complex being arranged around inversion center (Fig. 1). Each CuI is coordinated by two N atoms from one 2,2'-dipyridyldisuldide ligand, and two bridging Cl atoms, and displays a pyramidal geometry. In the centrosymmetric dinuclear complex, the Cu1···Cu1 separation is 3.076 (3) Å, whereas in the noncentrosymmetric molecule, the distance Cu2···Cu3 is slightly shorter 2.996 (1) Å.
For general background, see: Kadooka et al. (1976a,b); Delgado et al. (2006); Bell et al. (2000). For related literature, see: Kubo et al. (1998).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[Cu2Cl2(C10H8N2S2)2] | F(000) = 1920 |
Mr = 638.65 | Dx = 1.781 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6700 reflections |
a = 17.838 (3) Å | θ = 1.4–26.0° |
b = 9.4102 (17) Å | µ = 2.38 mm−1 |
c = 21.309 (4) Å | T = 298 K |
β = 92.594 (3)° | Block, red |
V = 3573.2 (11) Å3 | 0.33 × 0.19 × 0.11 mm |
Z = 6 |
Bruker APEXII area-detector diffractometer | 6349 independent reflections |
Radiation source: fine-focus sealed tube | 3331 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
φ and ω scans | θmax = 25.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→21 |
Tmin = 0.511, Tmax = 0.788 | k = −11→10 |
17489 measured reflections | l = −25→24 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3 |
6349 reflections | (Δ/σ)max < 0.001 |
433 parameters | Δρmax = 1.16 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
[Cu2Cl2(C10H8N2S2)2] | V = 3573.2 (11) Å3 |
Mr = 638.65 | Z = 6 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.838 (3) Å | µ = 2.38 mm−1 |
b = 9.4102 (17) Å | T = 298 K |
c = 21.309 (4) Å | 0.33 × 0.19 × 0.11 mm |
β = 92.594 (3)° |
Bruker APEXII area-detector diffractometer | 6349 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3331 reflections with I > 2σ(I) |
Tmin = 0.511, Tmax = 0.788 | Rint = 0.073 |
17489 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.03 | Δρmax = 1.16 e Å−3 |
6349 reflections | Δρmin = −0.47 e Å−3 |
433 parameters |
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 | ||
Cu1 | 0.44411 (5) | 0.90184 (10) | 0.46404 (5) | 0.0569 (3) | |
Cu2 | 0.22174 (5) | 1.03134 (10) | 0.21276 (5) | 0.0570 (3) | |
Cu3 | 0.11860 (5) | 0.84980 (11) | 0.13204 (5) | 0.0583 (3) | |
Cl1 | 0.53561 (10) | 1.0723 (2) | 0.42630 (8) | 0.0525 (5) | |
Cl2 | 0.12468 (11) | 0.8660 (2) | 0.24314 (9) | 0.0574 (5) | |
Cl3 | 0.21251 (10) | 1.0189 (2) | 0.10053 (9) | 0.0536 (5) | |
S1 | 0.28817 (12) | 0.7473 (3) | 0.38570 (11) | 0.0695 (7) | |
S2 | 0.33945 (13) | 0.6327 (2) | 0.45702 (11) | 0.0697 (7) | |
S3 | 0.33046 (11) | 1.2986 (2) | 0.22833 (10) | 0.0588 (6) | |
S4 | 0.37443 (11) | 1.1740 (2) | 0.29946 (9) | 0.0587 (6) | |
S5 | 0.01756 (12) | 0.5706 (2) | 0.11862 (10) | 0.0610 (6) | |
S6 | −0.01918 (12) | 0.6791 (2) | 0.04045 (10) | 0.0652 (6) | |
N1 | 0.4784 (3) | 0.7170 (6) | 0.4314 (3) | 0.0491 (16) | |
N2 | 0.3429 (3) | 0.9894 (7) | 0.4401 (3) | 0.0497 (16) | |
N3 | 0.3211 (3) | 0.9391 (7) | 0.2374 (3) | 0.0489 (16) | |
N4 | 0.1883 (3) | 1.2190 (7) | 0.2442 (3) | 0.0472 (15) | |
N5 | 0.0181 (3) | 0.9261 (7) | 0.1010 (3) | 0.0511 (16) | |
N6 | 0.1566 (3) | 0.6636 (6) | 0.0994 (3) | 0.0470 (15) | |
C1 | 0.5490 (4) | 0.6937 (8) | 0.4137 (3) | 0.053 (2) | |
H1 | 0.5816 | 0.7705 | 0.4120 | 0.064* | |
C2 | 0.5746 (5) | 0.5611 (9) | 0.3979 (4) | 0.064 (2) | |
H2 | 0.6241 | 0.5493 | 0.3868 | 0.076* | |
C3 | 0.5268 (6) | 0.4455 (10) | 0.3986 (4) | 0.076 (3) | |
H3 | 0.5431 | 0.3551 | 0.3880 | 0.092* | |
C4 | 0.4557 (6) | 0.4687 (9) | 0.4151 (4) | 0.074 (3) | |
H4 | 0.4221 | 0.3932 | 0.4157 | 0.088* | |
C5 | 0.4321 (4) | 0.6038 (9) | 0.4311 (3) | 0.054 (2) | |
C6 | 0.2844 (4) | 0.9278 (9) | 0.4103 (3) | 0.052 (2) | |
C7 | 0.2182 (5) | 1.0010 (11) | 0.3922 (4) | 0.068 (2) | |
H7 | 0.1783 | 0.9551 | 0.3711 | 0.082* | |
C8 | 0.2146 (5) | 1.1429 (11) | 0.4068 (4) | 0.072 (3) | |
H8 | 0.1724 | 1.1955 | 0.3943 | 0.087* | |
C9 | 0.2724 (5) | 1.2071 (9) | 0.4396 (4) | 0.061 (2) | |
H9 | 0.2694 | 1.3018 | 0.4516 | 0.073* | |
C10 | 0.3353 (4) | 1.1279 (9) | 0.4543 (4) | 0.055 (2) | |
H10 | 0.3753 | 1.1730 | 0.4755 | 0.066* | |
C11 | 0.3797 (4) | 0.9970 (8) | 0.2701 (3) | 0.049 (2) | |
C12 | 0.4435 (4) | 0.9214 (10) | 0.2871 (4) | 0.060 (2) | |
H12 | 0.4822 | 0.9637 | 0.3112 | 0.072* | |
C13 | 0.4493 (4) | 0.7817 (10) | 0.2679 (4) | 0.063 (2) | |
H13 | 0.4920 | 0.7285 | 0.2782 | 0.076* | |
C14 | 0.3903 (4) | 0.7239 (10) | 0.2334 (4) | 0.061 (2) | |
H14 | 0.3923 | 0.6298 | 0.2202 | 0.073* | |
C15 | 0.3291 (4) | 0.8041 (9) | 0.2186 (3) | 0.058 (2) | |
H15 | 0.2904 | 0.7635 | 0.1940 | 0.069* | |
C16 | 0.2350 (4) | 1.3303 (8) | 0.2478 (3) | 0.0472 (19) | |
C17 | 0.2137 (5) | 1.4648 (8) | 0.2623 (4) | 0.061 (2) | |
H17 | 0.2484 | 1.5384 | 0.2657 | 0.074* | |
C18 | 0.1379 (5) | 1.4881 (10) | 0.2720 (4) | 0.074 (3) | |
H18 | 0.1210 | 1.5792 | 0.2806 | 0.088* | |
C19 | 0.0888 (5) | 1.3782 (9) | 0.2690 (4) | 0.062 (2) | |
H19 | 0.0381 | 1.3923 | 0.2754 | 0.074* | |
C20 | 0.1165 (4) | 1.2438 (9) | 0.2562 (3) | 0.056 (2) | |
H20 | 0.0836 | 1.1672 | 0.2560 | 0.067* | |
C21 | 0.2300 (4) | 0.6443 (8) | 0.0883 (3) | 0.0471 (19) | |
H21 | 0.2598 | 0.7244 | 0.0837 | 0.056* | |
C22 | 0.2625 (4) | 0.5137 (9) | 0.0833 (3) | 0.055 (2) | |
H22 | 0.3132 | 0.5051 | 0.0755 | 0.067* | |
C23 | 0.2180 (5) | 0.3941 (9) | 0.0902 (4) | 0.063 (2) | |
H23 | 0.2391 | 0.3039 | 0.0882 | 0.076* | |
C24 | 0.1434 (5) | 0.4090 (9) | 0.0999 (3) | 0.056 (2) | |
H24 | 0.1125 | 0.3299 | 0.1031 | 0.067* | |
C25 | 0.1149 (4) | 0.5454 (8) | 0.1049 (3) | 0.0497 (19) | |
C26 | −0.0330 (4) | 0.8605 (9) | 0.0627 (3) | 0.051 (2) | |
C27 | −0.0934 (4) | 0.9273 (10) | 0.0358 (4) | 0.061 (2) | |
H27 | −0.1263 | 0.8774 | 0.0089 | 0.074* | |
C28 | −0.1066 (5) | 1.0680 (11) | 0.0479 (4) | 0.073 (3) | |
H28 | −0.1472 | 1.1153 | 0.0287 | 0.087* | |
C29 | −0.0572 (5) | 1.1379 (10) | 0.0900 (4) | 0.065 (2) | |
H29 | −0.0652 | 1.2317 | 0.1015 | 0.078* | |
C30 | 0.0038 (5) | 1.0631 (10) | 0.1138 (4) | 0.061 (2) | |
H30 | 0.0377 | 1.1108 | 0.1407 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0477 (6) | 0.0528 (7) | 0.0699 (7) | 0.0004 (5) | 0.0005 (5) | −0.0113 (5) |
Cu2 | 0.0449 (6) | 0.0503 (6) | 0.0751 (7) | 0.0010 (5) | −0.0038 (5) | −0.0115 (5) |
Cu3 | 0.0449 (6) | 0.0547 (7) | 0.0748 (7) | 0.0000 (5) | −0.0028 (5) | −0.0132 (5) |
Cl1 | 0.0493 (12) | 0.0519 (12) | 0.0559 (11) | −0.0076 (9) | −0.0009 (9) | 0.0004 (9) |
Cl2 | 0.0534 (12) | 0.0577 (13) | 0.0608 (12) | −0.0163 (10) | 0.0000 (9) | −0.0006 (10) |
Cl3 | 0.0507 (12) | 0.0505 (12) | 0.0590 (12) | −0.0097 (9) | −0.0028 (9) | 0.0025 (9) |
S1 | 0.0577 (14) | 0.0764 (17) | 0.0740 (15) | −0.0146 (12) | −0.0002 (11) | −0.0228 (13) |
S2 | 0.0680 (16) | 0.0623 (15) | 0.0811 (16) | −0.0174 (12) | 0.0277 (12) | −0.0040 (13) |
S3 | 0.0527 (13) | 0.0539 (13) | 0.0712 (14) | −0.0104 (10) | 0.0170 (10) | 0.0020 (11) |
S4 | 0.0541 (13) | 0.0649 (15) | 0.0568 (12) | −0.0144 (11) | −0.0009 (10) | −0.0118 (11) |
S5 | 0.0489 (13) | 0.0576 (14) | 0.0773 (14) | −0.0107 (10) | 0.0141 (11) | 0.0000 (12) |
S6 | 0.0555 (14) | 0.0730 (16) | 0.0660 (14) | −0.0055 (11) | −0.0094 (10) | −0.0142 (12) |
N1 | 0.042 (4) | 0.046 (4) | 0.060 (4) | −0.010 (3) | 0.009 (3) | −0.002 (3) |
N2 | 0.049 (4) | 0.061 (5) | 0.039 (3) | 0.007 (3) | 0.003 (3) | −0.004 (3) |
N3 | 0.039 (4) | 0.055 (4) | 0.053 (4) | 0.000 (3) | −0.002 (3) | −0.011 (3) |
N4 | 0.042 (4) | 0.051 (4) | 0.049 (4) | −0.003 (3) | 0.001 (3) | 0.001 (3) |
N5 | 0.054 (4) | 0.049 (4) | 0.051 (4) | 0.009 (3) | 0.011 (3) | 0.001 (3) |
N6 | 0.047 (4) | 0.042 (4) | 0.054 (4) | −0.007 (3) | 0.015 (3) | −0.005 (3) |
C1 | 0.055 (5) | 0.051 (5) | 0.054 (5) | 0.000 (4) | 0.000 (4) | −0.007 (4) |
C2 | 0.070 (6) | 0.051 (6) | 0.071 (6) | 0.012 (5) | 0.014 (5) | −0.005 (5) |
C3 | 0.093 (8) | 0.056 (6) | 0.081 (7) | 0.017 (6) | 0.026 (6) | −0.012 (5) |
C4 | 0.102 (8) | 0.042 (5) | 0.079 (6) | −0.001 (5) | 0.025 (6) | −0.007 (5) |
C5 | 0.051 (5) | 0.061 (6) | 0.052 (5) | 0.001 (4) | 0.015 (4) | −0.001 (4) |
C6 | 0.040 (5) | 0.067 (6) | 0.051 (4) | −0.008 (4) | 0.012 (4) | −0.010 (4) |
C7 | 0.058 (6) | 0.088 (8) | 0.059 (6) | −0.003 (5) | 0.001 (4) | −0.003 (5) |
C8 | 0.052 (6) | 0.084 (8) | 0.082 (6) | 0.010 (5) | 0.012 (5) | 0.002 (6) |
C9 | 0.061 (6) | 0.060 (6) | 0.063 (5) | 0.016 (5) | 0.014 (4) | 0.000 (4) |
C10 | 0.041 (5) | 0.059 (6) | 0.066 (5) | −0.002 (4) | 0.005 (4) | −0.006 (4) |
C11 | 0.045 (5) | 0.064 (5) | 0.040 (4) | −0.005 (4) | 0.016 (4) | 0.003 (4) |
C12 | 0.034 (5) | 0.081 (7) | 0.063 (5) | −0.001 (4) | −0.004 (4) | −0.002 (5) |
C13 | 0.047 (5) | 0.079 (7) | 0.065 (5) | 0.015 (5) | 0.007 (4) | 0.010 (5) |
C14 | 0.046 (5) | 0.072 (6) | 0.066 (5) | 0.018 (4) | 0.006 (4) | −0.002 (5) |
C15 | 0.050 (5) | 0.065 (6) | 0.056 (5) | 0.003 (4) | −0.004 (4) | −0.012 (4) |
C16 | 0.052 (5) | 0.045 (5) | 0.045 (4) | −0.003 (4) | 0.008 (4) | −0.005 (4) |
C17 | 0.076 (6) | 0.038 (5) | 0.072 (6) | −0.009 (4) | 0.018 (5) | −0.008 (4) |
C18 | 0.077 (7) | 0.063 (6) | 0.082 (7) | 0.008 (5) | 0.019 (5) | −0.006 (5) |
C19 | 0.065 (6) | 0.065 (6) | 0.055 (5) | 0.015 (5) | 0.013 (4) | −0.004 (4) |
C20 | 0.060 (6) | 0.051 (5) | 0.058 (5) | −0.007 (4) | 0.004 (4) | −0.001 (4) |
C21 | 0.046 (5) | 0.050 (5) | 0.046 (4) | −0.005 (4) | 0.009 (4) | −0.008 (4) |
C22 | 0.046 (5) | 0.058 (6) | 0.062 (5) | 0.003 (4) | 0.006 (4) | −0.012 (4) |
C23 | 0.079 (7) | 0.052 (6) | 0.057 (5) | 0.013 (5) | −0.003 (5) | −0.005 (4) |
C24 | 0.064 (6) | 0.044 (5) | 0.058 (5) | −0.004 (4) | 0.007 (4) | −0.003 (4) |
C25 | 0.050 (5) | 0.050 (5) | 0.049 (4) | −0.010 (4) | 0.005 (4) | −0.001 (4) |
C26 | 0.034 (4) | 0.076 (6) | 0.044 (4) | −0.002 (4) | 0.007 (3) | −0.006 (4) |
C27 | 0.050 (5) | 0.079 (7) | 0.054 (5) | −0.005 (5) | −0.006 (4) | 0.011 (5) |
C28 | 0.051 (6) | 0.082 (7) | 0.085 (7) | 0.015 (5) | 0.005 (5) | 0.020 (6) |
C29 | 0.063 (6) | 0.066 (6) | 0.068 (6) | 0.006 (5) | 0.016 (5) | 0.012 (5) |
C30 | 0.054 (5) | 0.075 (7) | 0.055 (5) | 0.012 (5) | 0.002 (4) | 0.003 (5) |
Cu1—N1 | 1.980 (6) | C4—H4 | 0.9300 |
Cu1—N2 | 2.028 (6) | C6—C7 | 1.405 (11) |
Cu1—Cl1i | 2.361 (2) | C7—C8 | 1.374 (12) |
Cu1—Cl1 | 2.450 (2) | C7—H7 | 0.9300 |
Cu2—N4 | 1.990 (6) | C8—C9 | 1.360 (11) |
Cu2—N3 | 2.022 (6) | C8—H8 | 0.9300 |
Cu2—Cl3 | 2.393 (2) | C9—C10 | 1.370 (10) |
Cu2—Cl2 | 2.437 (2) | C9—H9 | 0.9300 |
Cu2—Cu3 | 2.9959 (14) | C10—H10 | 0.9300 |
Cu3—N6 | 2.013 (6) | C11—C12 | 1.378 (10) |
Cu3—N5 | 2.015 (6) | C12—C13 | 1.381 (11) |
Cu3—Cl2 | 2.370 (2) | C12—H12 | 0.9300 |
Cu3—Cl3 | 2.427 (2) | C13—C14 | 1.370 (11) |
Cl1—Cu1i | 2.361 (2) | C13—H13 | 0.9300 |
S1—C6 | 1.779 (8) | C14—C15 | 1.353 (10) |
S1—S2 | 2.046 (4) | C14—H14 | 0.9300 |
S2—C5 | 1.786 (8) | C15—H15 | 0.9300 |
S3—C16 | 1.796 (7) | C16—C17 | 1.361 (10) |
S3—S4 | 2.044 (3) | C17—C18 | 1.393 (11) |
S4—C11 | 1.783 (8) | C17—H17 | 0.9300 |
S5—C25 | 1.790 (8) | C18—C19 | 1.355 (12) |
S5—S6 | 2.037 (3) | C18—H18 | 0.9300 |
S6—C26 | 1.791 (8) | C19—C20 | 1.390 (10) |
N1—C1 | 1.348 (9) | C19—H19 | 0.9300 |
N1—C5 | 1.349 (9) | C20—H20 | 0.9300 |
N2—C6 | 1.331 (9) | C21—C22 | 1.366 (10) |
N2—C10 | 1.347 (9) | C21—H21 | 0.9300 |
N3—C15 | 1.341 (9) | C22—C23 | 1.389 (11) |
N3—C11 | 1.345 (9) | C22—H22 | 0.9300 |
N4—C20 | 1.336 (9) | C23—C24 | 1.363 (10) |
N4—C16 | 1.338 (9) | C23—H23 | 0.9300 |
N5—C30 | 1.345 (10) | C24—C25 | 1.386 (10) |
N5—C26 | 1.346 (9) | C24—H24 | 0.9300 |
N6—C25 | 1.346 (9) | C26—C27 | 1.352 (10) |
N6—C21 | 1.353 (8) | C27—C28 | 1.371 (12) |
C1—C2 | 1.376 (10) | C27—H27 | 0.9300 |
C1—H1 | 0.9300 | C28—C29 | 1.392 (12) |
C2—C3 | 1.383 (12) | C28—H28 | 0.9300 |
C2—H2 | 0.9300 | C29—C30 | 1.373 (11) |
C3—C4 | 1.350 (11) | C29—H29 | 0.9300 |
C3—H3 | 0.9300 | C30—H30 | 0.9300 |
C4—C5 | 1.386 (11) | ||
N1—Cu1—N2 | 123.7 (3) | C8—C9—C10 | 118.0 (8) |
N1—Cu1—Cl1i | 113.69 (18) | C8—C9—H9 | 121.0 |
N2—Cu1—Cl1i | 107.54 (17) | C10—C9—H9 | 121.0 |
N1—Cu1—Cl1 | 103.82 (18) | N2—C10—C9 | 124.4 (8) |
N2—Cu1—Cl1 | 104.49 (19) | N2—C10—H10 | 117.8 |
Cl1i—Cu1—Cl1 | 100.54 (7) | C9—C10—H10 | 117.8 |
N4—Cu2—N3 | 124.5 (2) | N3—C11—C12 | 122.8 (8) |
N4—Cu2—Cl3 | 111.84 (17) | N3—C11—S4 | 120.5 (6) |
N3—Cu2—Cl3 | 104.99 (18) | C12—C11—S4 | 116.5 (6) |
N4—Cu2—Cl2 | 104.46 (18) | C11—C12—C13 | 119.0 (8) |
N3—Cu2—Cl2 | 106.35 (19) | C11—C12—H12 | 120.5 |
Cl3—Cu2—Cl2 | 102.51 (7) | C13—C12—H12 | 120.5 |
N6—Cu3—N5 | 120.4 (3) | C14—C13—C12 | 118.1 (8) |
N6—Cu3—Cl2 | 113.55 (18) | C14—C13—H13 | 120.9 |
N5—Cu3—Cl2 | 107.74 (17) | C12—C13—H13 | 120.9 |
N6—Cu3—Cl3 | 103.16 (17) | C15—C14—C13 | 119.7 (9) |
N5—Cu3—Cl3 | 106.90 (19) | C15—C14—H14 | 120.1 |
Cl2—Cu3—Cl3 | 103.49 (7) | C13—C14—H14 | 120.1 |
C6—S1—S2 | 107.8 (3) | N3—C15—C14 | 123.6 (8) |
C5—S2—S1 | 103.9 (3) | N3—C15—H15 | 118.2 |
C16—S3—S4 | 105.1 (3) | C14—C15—H15 | 118.2 |
C11—S4—S3 | 107.5 (3) | N4—C16—C17 | 124.1 (7) |
C25—S5—S6 | 102.2 (3) | N4—C16—S3 | 116.8 (5) |
C26—S6—S5 | 107.7 (3) | C17—C16—S3 | 119.0 (6) |
C1—N1—C5 | 116.7 (7) | C16—C17—C18 | 117.6 (8) |
C1—N1—Cu1 | 123.3 (5) | C16—C17—H17 | 121.2 |
C5—N1—Cu1 | 119.8 (5) | C18—C17—H17 | 121.2 |
C6—N2—C10 | 116.3 (7) | C19—C18—C17 | 120.1 (9) |
C6—N2—Cu1 | 127.9 (6) | C19—C18—H18 | 119.9 |
C10—N2—Cu1 | 115.8 (5) | C17—C18—H18 | 119.9 |
C15—N3—C11 | 116.6 (7) | C18—C19—C20 | 118.0 (8) |
C15—N3—Cu2 | 115.6 (5) | C18—C19—H19 | 121.0 |
C11—N3—Cu2 | 127.8 (5) | C20—C19—H19 | 121.0 |
C20—N4—C16 | 116.9 (7) | N4—C20—C19 | 123.3 (8) |
C20—N4—Cu2 | 121.6 (5) | N4—C20—H20 | 118.4 |
C16—N4—Cu2 | 121.2 (5) | C19—C20—H20 | 118.4 |
C30—N5—C26 | 115.7 (7) | N6—C21—C22 | 123.6 (7) |
C30—N5—Cu3 | 116.7 (5) | N6—C21—H21 | 118.2 |
C26—N5—Cu3 | 127.1 (5) | C22—C21—H21 | 118.2 |
C25—N6—C21 | 116.5 (6) | C21—C22—C23 | 118.3 (8) |
C25—N6—Cu3 | 119.6 (5) | C21—C22—H22 | 120.8 |
C21—N6—Cu3 | 121.4 (5) | C23—C22—H22 | 120.8 |
N1—C1—C2 | 122.8 (8) | C24—C23—C22 | 119.9 (8) |
N1—C1—H1 | 118.6 | C24—C23—H23 | 120.0 |
C2—C1—H1 | 118.6 | C22—C23—H23 | 120.0 |
C1—C2—C3 | 119.9 (8) | C23—C24—C25 | 118.1 (8) |
C1—C2—H2 | 120.1 | C23—C24—H24 | 121.0 |
C3—C2—H2 | 120.1 | C25—C24—H24 | 121.0 |
C4—C3—C2 | 117.6 (8) | N6—C25—C24 | 123.6 (7) |
C4—C3—H3 | 121.2 | N6—C25—S5 | 116.6 (6) |
C2—C3—H3 | 121.2 | C24—C25—S5 | 119.8 (6) |
C3—C4—C5 | 120.9 (9) | N5—C26—C27 | 123.2 (8) |
C3—C4—H4 | 119.6 | N5—C26—S6 | 120.0 (6) |
C5—C4—H4 | 119.6 | C27—C26—S6 | 116.6 (6) |
N1—C5—C4 | 122.1 (8) | C26—C27—C28 | 120.7 (8) |
N1—C5—S2 | 117.0 (6) | C26—C27—H27 | 119.7 |
C4—C5—S2 | 120.8 (7) | C28—C27—H27 | 119.7 |
N2—C6—C7 | 123.3 (8) | C27—C28—C29 | 117.9 (8) |
N2—C6—S1 | 121.1 (6) | C27—C28—H28 | 121.1 |
C7—C6—S1 | 115.4 (6) | C29—C28—H28 | 121.1 |
C8—C7—C6 | 117.4 (8) | C30—C29—C28 | 117.6 (9) |
C8—C7—H7 | 121.3 | C30—C29—H29 | 121.2 |
C6—C7—H7 | 121.3 | C28—C29—H29 | 121.2 |
C9—C8—C7 | 120.4 (9) | N5—C30—C29 | 124.8 (8) |
C9—C8—H8 | 119.8 | N5—C30—H30 | 117.6 |
C7—C8—H8 | 119.8 | C29—C30—H30 | 117.6 |
N4—Cu2—Cu3—N6 | 178.2 (3) | Cu1—N1—C1—C2 | 172.4 (6) |
N3—Cu2—Cu3—N6 | −7.0 (3) | N1—C1—C2—C3 | 1.4 (13) |
Cl3—Cu2—Cu3—N6 | 83.4 (2) | C1—C2—C3—C4 | 0.0 (13) |
Cl2—Cu2—Cu3—N6 | −98.6 (2) | C2—C3—C4—C5 | −0.4 (14) |
N4—Cu2—Cu3—N5 | 6.7 (3) | C1—N1—C5—C4 | 1.8 (11) |
N3—Cu2—Cu3—N5 | −178.4 (3) | Cu1—N1—C5—C4 | −173.1 (6) |
Cl3—Cu2—Cu3—N5 | −88.0 (2) | C1—N1—C5—S2 | 178.0 (5) |
Cl2—Cu2—Cu3—N5 | 90.0 (2) | Cu1—N1—C5—S2 | 3.2 (8) |
N4—Cu2—Cu3—Cl2 | −83.3 (2) | C3—C4—C5—N1 | −0.5 (14) |
N3—Cu2—Cu3—Cl2 | 91.5 (2) | C3—C4—C5—S2 | −176.6 (7) |
Cl3—Cu2—Cu3—Cl2 | −178.07 (9) | S1—S2—C5—N1 | 72.0 (6) |
N4—Cu2—Cu3—Cl3 | 94.8 (2) | S1—S2—C5—C4 | −111.7 (7) |
N3—Cu2—Cu3—Cl3 | −90.4 (2) | C10—N2—C6—C7 | 1.8 (11) |
Cl2—Cu2—Cu3—Cl3 | 178.07 (9) | Cu1—N2—C6—C7 | −175.6 (6) |
N1—Cu1—Cl1—Cu1i | −117.82 (19) | C10—N2—C6—S1 | 177.3 (5) |
N2—Cu1—Cl1—Cu1i | 111.39 (18) | Cu1—N2—C6—S1 | −0.1 (9) |
Cl1i—Cu1—Cl1—Cu1i | 0.0 | S2—S1—C6—N2 | 42.7 (6) |
N6—Cu3—Cl2—Cu2 | 109.55 (19) | S2—S1—C6—C7 | −141.5 (6) |
N5—Cu3—Cl2—Cu2 | −114.5 (2) | N2—C6—C7—C8 | −0.5 (12) |
Cl3—Cu3—Cl2—Cu2 | −1.55 (7) | S1—C6—C7—C8 | −176.2 (6) |
N4—Cu2—Cl2—Cu3 | 118.35 (17) | C6—C7—C8—C9 | −2.2 (13) |
N3—Cu2—Cl2—Cu3 | −108.39 (18) | C7—C8—C9—C10 | 3.4 (13) |
Cl3—Cu2—Cl2—Cu3 | 1.56 (7) | C6—N2—C10—C9 | −0.5 (11) |
N4—Cu2—Cl3—Cu3 | −112.90 (19) | Cu1—N2—C10—C9 | 177.2 (6) |
N3—Cu2—Cl3—Cu3 | 109.4 (2) | C8—C9—C10—N2 | −2.1 (12) |
Cl2—Cu2—Cl3—Cu3 | −1.53 (7) | C15—N3—C11—C12 | −3.8 (11) |
N6—Cu3—Cl3—Cu2 | −116.99 (19) | Cu2—N3—C11—C12 | 176.5 (6) |
N5—Cu3—Cl3—Cu2 | 115.18 (19) | C15—N3—C11—S4 | −178.2 (5) |
Cl2—Cu3—Cl3—Cu2 | 1.58 (7) | Cu2—N3—C11—S4 | 2.1 (9) |
C6—S1—S2—C5 | −103.2 (4) | S3—S4—C11—N3 | −46.4 (6) |
C16—S3—S4—C11 | 104.1 (4) | S3—S4—C11—C12 | 138.9 (5) |
C25—S5—S6—C26 | −105.7 (4) | N3—C11—C12—C13 | 2.7 (12) |
N2—Cu1—N1—C1 | 138.7 (6) | S4—C11—C12—C13 | 177.3 (6) |
Cl1i—Cu1—N1—C1 | −87.8 (6) | C11—C12—C13—C14 | −1.0 (12) |
Cl1—Cu1—N1—C1 | 20.4 (6) | C12—C13—C14—C15 | 0.7 (12) |
N2—Cu1—N1—C5 | −46.8 (7) | C11—N3—C15—C14 | 3.5 (11) |
Cl1i—Cu1—N1—C5 | 86.7 (6) | Cu2—N3—C15—C14 | −176.8 (6) |
Cl1—Cu1—N1—C5 | −165.1 (5) | C13—C14—C15—N3 | −2.0 (13) |
N1—Cu1—N2—C6 | 12.4 (7) | C20—N4—C16—C17 | −0.4 (11) |
Cl1i—Cu1—N2—C6 | −123.5 (6) | Cu2—N4—C16—C17 | 172.6 (6) |
Cl1—Cu1—N2—C6 | 130.3 (6) | C20—N4—C16—S3 | −177.4 (5) |
N1—Cu1—N2—C10 | −165.0 (5) | Cu2—N4—C16—S3 | −4.3 (8) |
Cl1i—Cu1—N2—C10 | 59.1 (5) | S4—S3—C16—N4 | −69.1 (6) |
Cl1—Cu1—N2—C10 | −47.1 (5) | S4—S3—C16—C17 | 113.7 (6) |
N4—Cu2—N3—C15 | 170.8 (5) | N4—C16—C17—C18 | −2.2 (12) |
Cl3—Cu2—N3—C15 | −58.6 (6) | S3—C16—C17—C18 | 174.7 (6) |
Cl2—Cu2—N3—C15 | 49.6 (6) | C16—C17—C18—C19 | 2.3 (13) |
Cu3—Cu2—N3—C15 | −3.8 (6) | C17—C18—C19—C20 | 0.1 (13) |
N4—Cu2—N3—C11 | −9.5 (7) | C16—N4—C20—C19 | 3.0 (10) |
Cl3—Cu2—N3—C11 | 121.2 (6) | Cu2—N4—C20—C19 | −170.0 (6) |
Cl2—Cu2—N3—C11 | −130.6 (6) | C18—C19—C20—N4 | −2.9 (12) |
Cu3—Cu2—N3—C11 | 175.9 (5) | C25—N6—C21—C22 | −0.9 (10) |
N3—Cu2—N4—C20 | −143.4 (5) | Cu3—N6—C21—C22 | 161.1 (6) |
Cl3—Cu2—N4—C20 | 88.7 (5) | N6—C21—C22—C23 | −0.1 (11) |
Cl2—Cu2—N4—C20 | −21.4 (6) | C21—C22—C23—C24 | 1.8 (11) |
Cu3—Cu2—N4—C20 | 30.8 (6) | C22—C23—C24—C25 | −2.3 (11) |
N3—Cu2—N4—C16 | 43.8 (6) | C21—N6—C25—C24 | 0.3 (11) |
Cl3—Cu2—N4—C16 | −84.0 (5) | Cu3—N6—C25—C24 | −162.0 (6) |
Cl2—Cu2—N4—C16 | 165.9 (5) | C21—N6—C25—S5 | −179.2 (5) |
Cu3—Cu2—N4—C16 | −141.9 (5) | Cu3—N6—C25—S5 | 18.4 (8) |
N6—Cu3—N5—C30 | −165.7 (5) | C23—C24—C25—N6 | 1.3 (11) |
Cl2—Cu3—N5—C30 | 61.9 (5) | C23—C24—C25—S5 | −179.2 (6) |
Cl3—Cu3—N5—C30 | −48.7 (5) | S6—S5—C25—N6 | 61.2 (6) |
Cu2—Cu3—N5—C30 | 5.6 (6) | S6—S5—C25—C24 | −118.3 (6) |
N6—Cu3—N5—C26 | 5.9 (7) | C30—N5—C26—C27 | 2.9 (11) |
Cl2—Cu3—N5—C26 | −126.5 (6) | Cu3—N5—C26—C27 | −168.7 (6) |
Cl3—Cu3—N5—C26 | 122.8 (6) | C30—N5—C26—S6 | 178.4 (5) |
Cu2—Cu3—N5—C26 | 177.2 (5) | Cu3—N5—C26—S6 | 6.8 (9) |
N5—Cu3—N6—C25 | −56.6 (6) | S5—S6—C26—N5 | 43.0 (6) |
Cl2—Cu3—N6—C25 | 73.3 (6) | S5—S6—C26—C27 | −141.2 (6) |
Cl3—Cu3—N6—C25 | −175.4 (5) | N5—C26—C27—C28 | −1.5 (12) |
Cu2—Cu3—N6—C25 | 132.1 (5) | S6—C26—C27—C28 | −177.1 (6) |
N5—Cu3—N6—C21 | 142.0 (5) | C26—C27—C28—C29 | −1.9 (12) |
Cl2—Cu3—N6—C21 | −88.2 (5) | C27—C28—C29—C30 | 3.6 (12) |
Cl3—Cu3—N6—C21 | 23.1 (6) | C26—N5—C30—C29 | −1.0 (11) |
Cu2—Cu3—N6—C21 | −29.4 (6) | Cu3—N5—C30—C29 | 171.5 (6) |
C5—N1—C1—C2 | −2.3 (11) | C28—C29—C30—N5 | −2.2 (13) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cu2Cl2(C10H8N2S2)2] |
Mr | 638.65 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 17.838 (3), 9.4102 (17), 21.309 (4) |
β (°) | 92.594 (3) |
V (Å3) | 3573.2 (11) |
Z | 6 |
Radiation type | Mo Kα |
µ (mm−1) | 2.38 |
Crystal size (mm) | 0.33 × 0.19 × 0.11 |
Data collection | |
Diffractometer | Bruker APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.511, 0.788 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17489, 6349, 3331 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.199, 1.03 |
No. of reflections | 6349 |
No. of parameters | 433 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.16, −0.47 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
Cu1—N1 | 1.980 (6) | Cu2—Cl3 | 2.393 (2) |
Cu1—N2 | 2.028 (6) | Cu2—Cl2 | 2.437 (2) |
Cu1—Cl1i | 2.361 (2) | Cu3—N6 | 2.013 (6) |
Cu1—Cl1 | 2.450 (2) | Cu3—N5 | 2.015 (6) |
Cu2—N4 | 1.990 (6) | Cu3—Cl2 | 2.370 (2) |
Cu2—N3 | 2.022 (6) | Cu3—Cl3 | 2.427 (2) |
N1—Cu1—N2 | 123.7 (3) | N4—Cu2—Cl2 | 104.46 (18) |
N1—Cu1—Cl1i | 113.69 (18) | N3—Cu2—Cl2 | 106.35 (19) |
N2—Cu1—Cl1i | 107.54 (17) | Cl3—Cu2—Cl2 | 102.51 (7) |
N1—Cu1—Cl1 | 103.82 (18) | N6—Cu3—N5 | 120.4 (3) |
N2—Cu1—Cl1 | 104.49 (19) | N6—Cu3—Cl2 | 113.55 (18) |
Cl1i—Cu1—Cl1 | 100.54 (7) | N5—Cu3—Cl2 | 107.74 (17) |
N4—Cu2—N3 | 124.5 (2) | N6—Cu3—Cl3 | 103.16 (17) |
N4—Cu2—Cl3 | 111.84 (17) | N5—Cu3—Cl3 | 106.90 (19) |
N3—Cu2—Cl3 | 104.99 (18) | Cl2—Cu3—Cl3 | 103.49 (7) |
C6—S1—S2—C5 | −103.2 (4) | C25—S5—S6—C26 | −105.7 (4) |
C16—S3—S4—C11 | 104.1 (4) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
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2,2'-dipyridyldisuldide possessing N-donnor and S-donnor is excellent candidates for the construction of metal complexes. Examples of crystal structure reports are copper(I) (Kadooka et al., 1976a,b; Kubo et al., 1998), copper(II) (Delgado et al., 2006), cobalt(II)(Kadooka et al., 1976b), mercury(II) (Bell et al., 2000). Recently, we obtained the title novel copper complex (I) by the reaction of cuprous chloride, 2,2'-dipyridyldisuldide in a dry ethanol and acetonitrile solution, and its crystal structure is reported here.
The asymmetric unit of the title compound is build up from one and a half dinuclear copper complexes; one of the dinuclear complex being arranged around inversion center (Fig. 1). Each CuI is coordinated by two N atoms from one 2,2'-dipyridyldisuldide ligand, and two bridging Cl atoms, and displays a pyramidal geometry. In the centrosymmetric dinuclear complex, the Cu1···Cu1 separation is 3.076 (3) Å, whereas in the noncentrosymmetric molecule, the distance Cu2···Cu3 is slightly shorter 2.996 (1) Å.