catena-Poly[[bis­[μ-1-(2-pyrid­yl)pyridinium-2-thiol­ate]-κ2N:S;κ2S:N-dicopper(I)]-di-μ-chloro]

Harding, P.; Harding, D.J.; Pakawatchai, C.; Phetmung, H.

doi:10.1107/S1600536806017028

catena-Poly[[bis[μ-1-(2-pyridyl)pyridinium-2-thiolate]-κ²N:S;κ²S:N-dicopper(I)]-di-μ-chloro]

P. Harding, D. J. Harding, C. Pakawatchai and H. Phetmung

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017028/ww2002sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017028/ww2002Isup2.hkl Contains datablock I

CCDC reference: 610923

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (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

Computing details top

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
M_r = 574.50	F(000) = 288
Triclinic, P1	D_x = 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	R_int = 0.011
Absorption correction: multi-scan SADABS (Bruker, 1997)	θ_max = 28.3°, θ_min = 2.4°
T_min = 0.700, T_max = 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	Δρ_max = 0.33 e Å⁻³
1455 reflections	Δρ_min = −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	U_iso*/U_eq
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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catena-Poly[[bis­[μ-1-(2-pyrid­yl)pyridinium-2-thiol­ate]-κ2N:S;κ2S:N-dicopper(I)]-di-μ-chloro]

Supporting information

Key indicators

checkCIF/PLATON results

catena-Poly[[bis[μ-1-(2-pyridyl)pyridinium-2-thiolate]-κ²N:S;κ²S:N-dicopper(I)]-di-μ-chloro]