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The reaction of copper(II) chloride with pyridine-2-thiol affords the title complex, [Cu2Cl2(C10H8N2S)2]n, in which two pyridine-2-thiol molecules have reacted to give a betain ligand and the copper centre has undergone reduction. The copper metal centre exhibits a distorted tetrahedral coordination geometry with bridging chloride and 1-(2-pyridyl)pyridinium-2-thiolate ligands, giving centrosymmetric dimers further linked into a polymeric chain.
Supporting information
CCDC reference: 610923
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
![[sigma]](https://journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.005 Å
- R factor = 0.025
- wR factor = 0.033
- Data-to-parameter ratio = 8.6
checkCIF/PLATON results
No syntax errors found
Alert level C
REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a
centrosymmetric structure
sine(theta)/lambda 0.6664
Proportion of unique data used 0.5556
Ratio reflections to parameters 8.6095
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.61
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 8
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: Xtal3.7 (Hall et al., 2000); program(s) used to solve structure: Xtal 3.7; program(s) used to refine structure: Xtal 3.7; molecular graphics: Xtal 3.7; software used to prepare material for publication: Xtal 3.7.
catena-Poly[[bis[µ-1-(2-pyridyl)pyridinium-2-thiolate]-
κ2N:
S;
κ2S:
N- dicopper(II)]-di-µ-chloro]
top
Crystal data top
| [Cu2Cl2(C10H8N2S)2] | Z = 1 |
| Mr = 574.50 | F(000) = 288 |
| Triclinic, P1 | Dx = 1.806 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.6268 (11) Å | Cell parameters from 2642 reflections |
| b = 8.7596 (13) Å | θ = 2.4–28.3° |
| c = 9.2748 (14) Å | µ = 2.48 mm−1 |
| α = 72.340 (2)° | T = 298 K |
| β = 70.924 (2)° | Block, red [orange?] |
| γ = 67.088 (2)° | 0.23 × 0.12 × 0.09 mm |
| V = 528.24 (14) Å3 | |
Data collection top
Bruker SMART CCD area-detector
diffractometer | 1455 reflections with F > 3.98σ(F) |
| φ and ω scans | Rint = 0.011 |
Absorption correction: multi-scan
SADABS (Bruker, 1997) | θmax = 28.3°, θmin = 2.4° |
| Tmin = 0.700, Tmax = 0.804 | h = −10→9 |
| 4641 measured reflections | k = −11→11 |
| 2619 independent reflections | l = −11→12 |
Refinement top
| Refinement on F | 0 constraints |
| Least-squares matrix: full | All H-atom parameters refined |
| R[F2 > 2σ(F2)] = 0.025 | weighting scheme |
| wR(F2) = 0.033 | (Δ/σ)max = 0.033 |
| S = 1.09 | Δρmax = 0.33 e Å−3 |
| 1455 reflections | Δρmin = −0.29 e Å−3 |
| 169 parameters | Extinction correction: Larson (1970), Larson (1970) |
| 0 restraints | Extinction coefficient: 394 (120) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| Cu1 | 0.49338 (6) | 0.00929 (5) | −0.83260 (4) | 0.0358 (5) | |
| Cl1 | 0.23473 (11) | 0.09623 (9) | −0.95283 (8) | 0.0338 (9) | |
| S1 | 0.48155 (11) | −0.16989 (9) | −0.59946 (8) | 0.0300 (9) | |
| C1 | 0.6903 (4) | −0.2044 (3) | −0.5485 (3) | 0.026 (3) | |
| C2 | 0.8559 (5) | −0.1619 (4) | −0.6527 (3) | 0.033 (4) | |
| C3 | 1.0130 (5) | −0.1807 (4) | −0.6036 (4) | 0.039 (4) | |
| C4 | 1.0185 (5) | −0.2453 (5) | −0.4470 (4) | 0.045 (4) | |
| C5 | 0.8633 (5) | −0.2905 (4) | −0.3475 (4) | 0.036 (4) | |
| N1 | 0.7062 (3) | −0.2732 (3) | −0.3972 (2) | 0.024 (3) | |
| N2 | 0.5544 (3) | 0.2239 (3) | −0.8241 (3) | 0.028 (3) | |
| C6 | 0.7056 (4) | 0.2661 (4) | −0.9321 (3) | 0.036 (3) | |
| C7 | 0.7539 (5) | 0.4044 (4) | −0.9379 (3) | 0.037 (3) | |
| C8 | 0.6438 (5) | 0.5069 (4) | −0.8321 (4) | 0.039 (4) | |
| C9 | 0.4900 (5) | 0.4642 (4) | −0.7189 (3) | 0.035 (3) | |
| C10 | 0.4546 (4) | 0.3216 (3) | −0.7195 (3) | 0.025 (3) | |
| H5 | 0.856 (5) | −0.337 (4) | −0.239 (4) | 0.040 (8)* | |
| H6 | 0.778 (4) | 0.197 (4) | −1.010 (3) | 0.031 (7)* | |
| H3 | 1.123 (5) | −0.149 (4) | −0.676 (4) | 0.055 (9)* | |
| H7 | 0.856 (5) | 0.427 (4) | −1.016 (4) | 0.050 (9)* | |
| H8 | 0.674 (5) | 0.608 (4) | −0.834 (3) | 0.043 (8)* | |
| H9 | 0.410 (5) | 0.525 (4) | −0.642 (4) | 0.055 (10)* | |
| H2 | 0.851 (5) | −0.116 (4) | −0.754 (4) | 0.033 (8)* | |
| H4 | 1.114 (6) | −0.252 (5) | −0.405 (4) | 0.057 (11)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Cu1 | 0.0391 (3) | 0.0415 (3) | 0.0298 (3) | −0.0178 (3) | −0.0107 (2) | −0.0020 (2) |
| Cl1 | 0.0285 (5) | 0.0450 (5) | 0.0292 (4) | −0.0109 (4) | −0.0069 (4) | −0.0105 (4) |
| S1 | 0.0296 (5) | 0.0378 (4) | 0.0267 (4) | −0.0178 (4) | −0.0096 (4) | 0.0001 (4) |
| C1 | 0.0282 (17) | 0.0261 (14) | 0.0230 (14) | −0.0091 (14) | −0.0068 (14) | −0.0031 (13) |
| C2 | 0.030 (2) | 0.0458 (19) | 0.0220 (16) | −0.0148 (18) | −0.0066 (17) | −0.0002 (16) |
| C3 | 0.025 (2) | 0.055 (2) | 0.0337 (18) | −0.0176 (18) | −0.0060 (17) | −0.0011 (17) |
| C4 | 0.033 (2) | 0.067 (3) | 0.038 (2) | −0.023 (2) | −0.014 (2) | −0.003 (2) |
| C5 | 0.033 (2) | 0.049 (2) | 0.0248 (16) | −0.0148 (19) | −0.0134 (17) | 0.0002 (16) |
| N1 | 0.0226 (14) | 0.0294 (13) | 0.0216 (12) | −0.0094 (12) | −0.0091 (12) | −0.0015 (11) |
| N2 | 0.0300 (14) | 0.0304 (12) | 0.0253 (12) | −0.0135 (12) | −0.0058 (12) | −0.0033 (11) |
| C6 | 0.0338 (19) | 0.0396 (16) | 0.0307 (16) | −0.0144 (16) | −0.0014 (16) | −0.0062 (15) |
| C7 | 0.035 (2) | 0.0396 (17) | 0.0346 (17) | −0.0206 (17) | −0.0052 (17) | 0.0041 (15) |
| C8 | 0.047 (2) | 0.0321 (16) | 0.0438 (19) | −0.0218 (18) | −0.0157 (18) | 0.0029 (15) |
| C9 | 0.040 (2) | 0.0295 (15) | 0.0353 (16) | −0.0131 (16) | −0.0081 (17) | −0.0059 (15) |
| C10 | 0.0255 (17) | 0.0288 (14) | 0.0214 (14) | −0.0095 (15) | −0.0103 (14) | 0.0017 (13) |
Geometric parameters (Å, º) top
| Cu1—Cl1 | 2.3384 (10) | C5—N1 | 1.360 (5) |
| Cu1—S1 | 2.2518 (8) | C5—H5 | 0.95 (3) |
| Cu1—N2 | 2.133 (3) | N1—C10 | 1.454 (3) |
| Cu1—Cu1 | 3.1254 (8) | N2—C6 | 1.350 (4) |
| Cu1—Cl1 | 2.4579 (8) | N2—C10 | 1.329 (4) |
| S1—C1 | 1.697 (3) | C6—C7 | 1.379 (6) |
| C1—C2 | 1.421 (4) | C6—H6 | 0.97 (3) |
| C1—N1 | 1.375 (3) | C7—C8 | 1.372 (4) |
| C2—C3 | 1.352 (6) | C7—H7 | 0.91 (3) |
| C2—H2 | 0.91 (3) | C8—C9 | 1.384 (4) |
| C3—C4 | 1.398 (5) | C8—H8 | 0.99 (4) |
| C3—H3 | 0.96 (4) | C9—C10 | 1.380 (5) |
| C4—C5 | 1.356 (5) | C9—H9 | 0.93 (4) |
| C4—H4 | 0.91 (5) | | |
| | | |
| Cu1···C1 | 3.179 (3) | C5···C10 | 2.401 (5) |
| Cu1···C2 | 3.309 (4) | C5···H4 | 1.94 (5) |
| Cu1···C5 | 3.251 (3) | N1···N2 | 2.356 (3) |
| Cu1···N1 | 3.215 (2) | N1···C9 | 2.450 (4) |
| Cu1···C6 | 3.022 (4) | N1···H5 | 1.97 (4) |
| Cu1···C10 | 3.095 (3) | N1···H9 | 2.57 (4) |
| Cu1···H6 | 2.99 (3) | N2···C7 | 2.396 (5) |
| Cu1···H2 | 2.77 (4) | N2···C8 | 2.790 (5) |
| Cl1···H6 | 2.74 (4) | N2···C9 | 2.399 (5) |
| S1···C2 | 2.760 (4) | N2···H6 | 1.99 (3) |
| S1···N1 | 2.672 (3) | C6···C8 | 2.378 (5) |
| S1···C10 | 2.968 (3) | C6···C9 | 2.713 (4) |
| C1···C3 | 2.424 (5) | C6···C10 | 2.275 (4) |
| C1···C4 | 2.814 (6) | C6···H7 | 1.98 (4) |
| C1···C5 | 2.402 (5) | C7···C9 | 2.367 (4) |
| C1···C10 | 2.448 (3) | C7···C10 | 2.686 (4) |
| C1···H2 | 2.01 (3) | C7···H6 | 2.04 (4) |
| C2···C4 | 2.388 (6) | C7···H8 | 2.07 (4) |
| C2···C5 | 2.721 (4) | C8···C10 | 2.370 (5) |
| C2···N1 | 2.359 (3) | C8···H7 | 2.01 (3) |
| C2···H3 | 2.02 (4) | C8···H9 | 2.05 (3) |
| C3···C5 | 2.360 (4) | C9···H8 | 2.07 (4) |
| C3···N1 | 2.721 (4) | C10···H5 | 2.47 (4) |
| C3···H2 | 1.97 (4) | C10···H9 | 1.99 (4) |
| C3···H4 | 2.06 (4) | H5···H4 | 2.29 (5) |
| C4···N1 | 2.369 (5) | H6···H7 | 2.29 (6) |
| C4···H5 | 2.04 (3) | H3···H2 | 2.30 (6) |
| C4···H3 | 2.04 (3) | H3···H4 | 2.38 (5) |
| C5···N2 | 2.971 (4) | H7···H8 | 2.38 (5) |
| | | |
| Cl1—Cu1—S1 | 119.35 (3) | C4—C5—N1 | 121.5 (3) |
| Cl1—Cu1—N2 | 110.16 (7) | C4—C5—H5 | 123 (2) |
| Cl1—Cu1—Cu1 | 51.02 (2) | N1—C5—H5 | 115 (2) |
| Cl1—Cu1—Cl1 | 98.71 (3) | C1—N1—C5 | 122.9 (2) |
| S1—Cu1—N2 | 110.08 (7) | C1—N1—C10 | 119.9 (3) |
| S1—Cu1—Cu1 | 135.15 (3) | C5—N1—C10 | 117.1 (2) |
| S1—Cu1—Cl1 | 115.80 (3) | Cu1—N2—C6 | 118.6 (2) |
| N2—Cu1—Cu1 | 113.93 (6) | Cu1—N2—C10 | 125.1 (2) |
| N2—Cu1—Cl1 | 100.84 (6) | C6—N2—C10 | 116.3 (3) |
| Cu1—Cu1—Cl1 | 47.69 (2) | N2—C6—C7 | 122.8 (3) |
| Cu1—Cl1—Cu1 | 81.29 (3) | N2—C6—H6 | 117 (2) |
| Cu1—S1—C1 | 106.38 (9) | C7—C6—H6 | 120 (2) |
| S1—C1—C2 | 124.3 (2) | C6—C7—C8 | 119.7 (3) |
| S1—C1—N1 | 120.5 (2) | C6—C7—H7 | 118 (3) |
| C2—C1—N1 | 115.1 (3) | C8—C7—H7 | 122 (3) |
| C1—C2—C3 | 121.9 (3) | C7—C8—C9 | 118.4 (4) |
| C1—C2—H2 | 118 (2) | C7—C8—H8 | 121.4 (16) |
| C3—C2—H2 | 120 (2) | C9—C8—H8 | 120.2 (16) |
| C2—C3—C4 | 120.6 (3) | C8—C9—C10 | 118.1 (3) |
| C2—C3—H3 | 120 (2) | C8—C9—H9 | 124 (3) |
| C4—C3—H3 | 119 (2) | C10—C9—H9 | 118 (3) |
| C3—C4—C5 | 117.9 (4) | N2—C10—C9 | 124.6 (3) |
| C3—C4—H4 | 125 (2) | N2—C10—N1 | 115.6 (3) |
| C5—C4—H4 | 117 (2) | C9—C10—N1 | 119.7 (2) |
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