Crystal structure of bis­[1,3,4,5-tetra­methyl-1H-imidazole-2(3H)-thione-κS]chlorido­copper(I)

Flörke, U.; Ahmida, A.; Egold, H.; Henkel, G.

doi:10.1107/S1600536814024404

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages m397-m398

doi:10.1107/S1600536814024404

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Crystal structure of bis[1,3,4,5-tetramethyl-1H-imidazole-2(3H)-thione-κS]chloridocopper(I)

Ulrich Flörke,^a ^* Aziza Ahmida,^a Hans Egold ^a and Gerald Henkel ^a

^aDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
^*Correspondence e-mail: ulrich.floerke@upb.de

Edited by O. Blacque, University of Zürich, Switzerland (Received 3 November 2014; accepted 6 November 2014; online 15 November 2014)

The molecular structure of the title compound, [CuCl(C₇H₁₂N₂S)₂], shows a slightly distorted trigonal–planar coordination geometry of the Cu atom. The Cu—Cl bond measures 2.2287 (9) Å, and the two Cu—S bonds are significantly different from each other, with values of 2.2270 (10) and 2.2662 (10) Å. Also, the S—Cu—Cl angles differ, with values of 113.80 (4) and 124.42 (4)°, while the S—Cu—S angle is 121.51 (4)°. The two imidazole rings are almost parallel, making a dihedral angle of 2.1 (2)°. In the crystal, the shortest C—H⋯Cl interactions stabilize a three-dimensional network with molecules linked into centrosymmetric dimers that are stacked along the b-axis direction.

Keywords: crystal structure; trigonal coordination; copper; imidazole.

CCDC reference: 1032971

1. Related literature

For structures of related Cu complexes, see: Devillanova et al. (1980 ); Kimani et al. (2011 ). For background to effective anti-oxidants, see: Bhabak et al. (2010 ); Yamashita & Yamashita (2010 ).

2. Experimental

2.1. Crystal data

[CuCl(C₇H₁₂N₂S)₂]
M_r = 411.48
Monoclinic, P 2₁ /n
a = 9.4738 (14) Å
b = 13.662 (2) Å
c = 14.119 (2) Å
β = 98.314 (3)°
V = 1808.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.59 mm⁻¹
T = 120 K
0.25 × 0.20 × 0.11 mm

2.2. Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.692, T_max = 0.845
17386 measured reflections
4304 independent reflections
2584 reflections with I > 2σ(I)
R_int = 0.099

2.3. Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.091
S = 0.85
4304 reflections
207 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯Cl1ⁱ	0.98	2.75	3.717 (4)	170
C11—H11A⋯Cl1ⁱⁱ	0.98	2.76	3.721 (3)	165
C14—H14B⋯Cl1ⁱⁱⁱ	0.98	2.80	3.782 (4)	176
Symmetry codes: (i) -x-1, -y+1, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

CCDC reference: 1032971

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814024404/zq2228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814024404/zq2228Isup2.hkl

checkCIF report

Comment top

We are interested in the chemistry of N,N-dimethylimidazole-thione derivatives due to their ability to act as effective antioxidants (Bhabak et al., 2010; Yamashita et al., 2010). Here we report the synthesis of a copper(I) chloride complex with 1,3,4,5-tetra-methylimidazole-2-thione ligands.

The title compound shows the same trans configuration as the bis-N,N'-dimethylimidazole-thione-Cu(I) compound (Kimani et al., 2011) or bis-N,N'-dimethylimidazolidine-thione-CuCl (Devillanova et al., 1980) whereas the cis configuration is also known for bis-N,N'-dimethylimidazole-thione-CuX (X = Cl, Br, I) (Kimani et al., 2011). In contrast to all the reported complexes in the title compound both Cu and Cl atoms lie on general positions and the two Cu—S bond lengths differ strongly with Cu–S1 2.2662 (10) and Cu–S2 2.2270 (10) Å. Also the S—Cu—Cl angles differ with 113.80 (4)° and 124.41 (4)°, while the S—Cu—S angle is 121.51 (4)°.

The intramolecular hydrogen bonds between the chlorine atom and hydrogen atoms of the methyl group amount to 4.838 (H2b—Cl) and 4.911 Å(H9a—Cl).

Related literature top

For structures of related Cu complexes, see: Devillanova et al. (1980); Kimani et al. (2011). For background to effective anti-oxidants, see: Bhabak et al. (2010); Yamashita et al. (2010)

Experimental top

To a solution of 1,3,4,5-tetra-methylimidazoline-2-thione (0.390 mg, 2.75 mmol) in acetonitrile (50 ml) CuCl₂ (0.168 mg, 1.25 mmol) was added and the mixture was stirred at room temperature for 24 h. Afterwards the solvent was removed under vacuum. White crystals were obtained from diffusion of diethyl ether into acetonitrile.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

Molecular structure of the title compound with anisotropic displacement parameters drawn at the 50% probability level.

Bis[1,3,4,5-tetramethyl-1H-imidazole-2(3H)-thione-κS]chloridocopper(I) top

Crystal data top

[CuCl(C₇H₁₂N₂S)₂]	F(000) = 856
M_r = 411.48	D_x = 1.512 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.4738 (14) Å	Cell parameters from 2398 reflections
b = 13.662 (2) Å	θ = 2.6–23.8°
c = 14.119 (2) Å	µ = 1.59 mm⁻¹
β = 98.314 (3)°	T = 120 K
V = 1808.2 (5) Å³	Prism, blue
Z = 4	0.25 × 0.20 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4304 independent reflections
Radiation source: sealed tube	2584 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
T_min = 0.692, T_max = 0.845	k = −17→16
17386 measured reflections	l = −18→18

Refinement top

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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F²) = 0.091	H-atom parameters constrained
S = 0.85	w = 1/[σ²(F_o²) + (0.0349P)²] where P = (F_o² + 2F_c²)/3
4304 reflections	(Δ/σ)_max = 0.001
207 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[CuCl(C₇H₁₂N₂S)₂]	V = 1808.2 (5) Å³
M_r = 411.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4738 (14) Å	µ = 1.59 mm⁻¹
b = 13.662 (2) Å	T = 120 K
c = 14.119 (2) Å	0.25 × 0.20 × 0.11 mm
β = 98.314 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4304 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2584 reflections with I > 2σ(I)
T_min = 0.692, T_max = 0.845	R_int = 0.099
17386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 0.85	Δρ_max = 0.52 e Å⁻³
4304 reflections	Δρ_min = −0.58 e Å⁻³
207 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	−0.42892 (4)	0.63369 (3)	0.67946 (3)	0.02856 (13)
Cl1	−0.50281 (8)	0.51059 (6)	0.76351 (6)	0.0275 (2)
S1	−0.18839 (9)	0.64545 (9)	0.69146 (7)	0.0453 (3)
S2	−0.57219 (9)	0.74573 (7)	0.60170 (6)	0.0308 (2)
N1	−0.1745 (3)	0.5835 (2)	0.5081 (2)	0.0312 (7)
N2	−0.0533 (3)	0.71469 (19)	0.54686 (19)	0.0215 (6)
N3	−0.4380 (3)	0.77570 (19)	0.44451 (19)	0.0224 (6)
N4	−0.3860 (3)	0.88515 (19)	0.55378 (19)	0.0246 (7)
C1	−0.1411 (3)	0.6492 (2)	0.5796 (2)	0.0264 (8)
C2	−0.2621 (4)	0.4972 (3)	0.5142 (3)	0.0497 (12)
H2A	−0.2016	0.4387	0.5193	0.075*
H2B	−0.3333	0.4926	0.4567	0.075*
H2C	−0.3106	0.5021	0.5709	0.075*
C3	−0.1069 (3)	0.6088 (3)	0.4301 (3)	0.0325 (9)
C4	−0.1248 (4)	0.5507 (3)	0.3408 (3)	0.0578 (13)
H4A	−0.0819	0.5860	0.2916	0.087*
H4B	−0.2266	0.5406	0.3187	0.087*
H4C	−0.0776	0.4872	0.3529	0.087*
C5	−0.0309 (3)	0.6901 (3)	0.4548 (2)	0.0273 (8)
C6	0.0632 (4)	0.7501 (3)	0.4023 (3)	0.0421 (10)
H6A	0.0681	0.7205	0.3396	0.063*
H6B	0.1591	0.7528	0.4391	0.063*
H6C	0.0244	0.8165	0.3935	0.063*
C7	0.0058 (3)	0.8007 (2)	0.5986 (3)	0.0301 (8)
H7A	−0.0400	0.8098	0.6559	0.045*
H7B	−0.0113	0.8584	0.5573	0.045*
H7C	0.1087	0.7918	0.6174	0.045*
C8	−0.4618 (3)	0.8033 (2)	0.5325 (2)	0.0238 (8)
C9	−0.5003 (4)	0.6902 (2)	0.3929 (3)	0.0320 (9)
H9A	−0.5329	0.6440	0.4382	0.048*
H9B	−0.4286	0.6586	0.3597	0.048*
H9C	−0.5816	0.7106	0.3460	0.048*
C10	−0.3462 (3)	0.8419 (2)	0.4094 (2)	0.0229 (8)
C11	−0.3028 (3)	0.8309 (3)	0.3134 (2)	0.0285 (8)
H11A	−0.2349	0.8828	0.3034	0.043*
H11B	−0.3870	0.8358	0.2644	0.043*
H11C	−0.2576	0.7669	0.3088	0.043*
C12	−0.3132 (3)	0.9106 (2)	0.4776 (2)	0.0248 (8)
C13	−0.2251 (3)	1.0006 (2)	0.4780 (3)	0.0314 (8)
H13A	−0.1750	1.0005	0.4220	0.047*
H13B	−0.1553	1.0023	0.5365	0.047*
H13C	−0.2868	1.0583	0.4759	0.047*
C14	−0.3773 (4)	0.9387 (3)	0.6430 (3)	0.0350 (9)
H14A	−0.4383	0.9969	0.6336	0.052*
H14B	−0.2784	0.9587	0.6638	0.052*
H14C	−0.4095	0.8967	0.6919	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0284 (2)	0.0310 (3)	0.0266 (2)	−0.0035 (2)	0.00511 (17)	0.0040 (2)
Cl1	0.0260 (4)	0.0266 (5)	0.0307 (5)	−0.0004 (4)	0.0067 (4)	0.0052 (4)
S1	0.0254 (5)	0.0805 (9)	0.0295 (5)	−0.0085 (5)	0.0023 (4)	0.0173 (6)
S2	0.0249 (4)	0.0367 (6)	0.0314 (5)	−0.0010 (4)	0.0059 (4)	0.0092 (4)
N1	0.0220 (14)	0.0205 (16)	0.049 (2)	−0.0061 (13)	−0.0017 (14)	0.0012 (15)
N2	0.0190 (13)	0.0205 (15)	0.0247 (16)	−0.0006 (11)	0.0024 (11)	−0.0018 (12)
N3	0.0215 (14)	0.0216 (16)	0.0239 (16)	−0.0023 (12)	0.0021 (11)	0.0001 (12)
N4	0.0237 (14)	0.0258 (17)	0.0246 (16)	−0.0023 (12)	0.0045 (12)	−0.0019 (13)
C1	0.0163 (15)	0.028 (2)	0.034 (2)	−0.0002 (14)	0.0005 (14)	0.0082 (17)
C2	0.031 (2)	0.027 (2)	0.087 (4)	−0.0087 (18)	−0.008 (2)	0.009 (2)
C3	0.0194 (17)	0.038 (2)	0.039 (2)	0.0031 (16)	0.0017 (16)	−0.0098 (18)
C4	0.035 (2)	0.073 (3)	0.063 (3)	0.001 (2)	0.000 (2)	−0.041 (3)
C5	0.0221 (17)	0.035 (2)	0.025 (2)	0.0030 (15)	0.0012 (14)	0.0000 (16)
C6	0.037 (2)	0.062 (3)	0.028 (2)	−0.009 (2)	0.0079 (17)	0.005 (2)
C7	0.0293 (18)	0.026 (2)	0.034 (2)	−0.0014 (16)	0.0013 (16)	−0.0028 (17)
C8	0.0200 (16)	0.0241 (19)	0.027 (2)	0.0005 (14)	0.0007 (14)	0.0051 (15)
C9	0.034 (2)	0.026 (2)	0.036 (2)	−0.0061 (16)	0.0028 (16)	−0.0009 (17)
C10	0.0211 (16)	0.023 (2)	0.0247 (19)	0.0016 (14)	0.0031 (14)	0.0060 (15)
C11	0.0272 (18)	0.033 (2)	0.024 (2)	−0.0006 (15)	0.0008 (15)	0.0046 (16)
C12	0.0262 (17)	0.0231 (19)	0.026 (2)	−0.0001 (15)	0.0047 (15)	0.0043 (16)
C13	0.0283 (18)	0.028 (2)	0.037 (2)	−0.0005 (16)	0.0021 (16)	−0.0017 (17)
C14	0.033 (2)	0.042 (2)	0.030 (2)	−0.0038 (17)	0.0078 (17)	−0.0098 (18)

Geometric parameters (Å, º) top

Cu1—S2	2.2270 (10)	C4—H4C	0.9800
Cu1—Cl1	2.2287 (9)	C5—C6	1.486 (5)
Cu1—S1	2.2662 (10)	C6—H6A	0.9800
S1—C1	1.704 (4)	C6—H6B	0.9800
S2—C8	1.721 (3)	C6—H6C	0.9800
N1—C1	1.354 (4)	C7—H7A	0.9800
N1—C3	1.395 (4)	C7—H7B	0.9800
N1—C2	1.451 (4)	C7—H7C	0.9800
N2—C1	1.348 (4)	C9—H9A	0.9800
N2—C5	1.388 (4)	C9—H9B	0.9800
N2—C7	1.452 (4)	C9—H9C	0.9800
N3—C8	1.349 (4)	C10—C12	1.349 (5)
N3—C10	1.395 (4)	C10—C11	1.480 (4)
N3—C9	1.456 (4)	C11—H11A	0.9800
N4—C8	1.339 (4)	C11—H11B	0.9800
N4—C12	1.402 (4)	C11—H11C	0.9800
N4—C14	1.449 (4)	C12—C13	1.486 (4)
C2—H2A	0.9800	C13—H13A	0.9800
C2—H2B	0.9800	C13—H13B	0.9800
C2—H2C	0.9800	C13—H13C	0.9800
C3—C5	1.342 (5)	C14—H14A	0.9800
C3—C4	1.479 (5)	C14—H14B	0.9800
C4—H4A	0.9800	C14—H14C	0.9800
C4—H4B	0.9800

S2—Cu1—Cl1	124.42 (4)	H6A—C6—H6C	109.5
S2—Cu1—S1	121.51 (4)	H6B—C6—H6C	109.5
Cl1—Cu1—S1	113.80 (4)	N2—C7—H7A	109.5
C1—S1—Cu1	109.23 (11)	N2—C7—H7B	109.5
C8—S2—Cu1	102.52 (11)	H7A—C7—H7B	109.5
C1—N1—C3	109.8 (3)	N2—C7—H7C	109.5
C1—N1—C2	124.6 (3)	H7A—C7—H7C	109.5
C3—N1—C2	125.5 (3)	H7B—C7—H7C	109.5
C1—N2—C5	110.2 (3)	N4—C8—N3	106.5 (3)
C1—N2—C7	125.3 (3)	N4—C8—S2	127.2 (3)
C5—N2—C7	124.5 (3)	N3—C8—S2	126.3 (3)
C8—N3—C10	110.1 (3)	N3—C9—H9A	109.5
C8—N3—C9	125.1 (3)	N3—C9—H9B	109.5
C10—N3—C9	124.8 (3)	H9A—C9—H9B	109.5
C8—N4—C12	110.0 (3)	N3—C9—H9C	109.5
C8—N4—C14	125.3 (3)	H9A—C9—H9C	109.5
C12—N4—C14	124.7 (3)	H9B—C9—H9C	109.5
N2—C1—N1	105.9 (3)	C12—C10—N3	106.8 (3)
N2—C1—S1	126.6 (3)	C12—C10—C11	131.2 (3)
N1—C1—S1	127.4 (3)	N3—C10—C11	122.0 (3)
N1—C2—H2A	109.5	C10—C11—H11A	109.5
N1—C2—H2B	109.5	C10—C11—H11B	109.5
H2A—C2—H2B	109.5	H11A—C11—H11B	109.5
N1—C2—H2C	109.5	C10—C11—H11C	109.5
H2A—C2—H2C	109.5	H11A—C11—H11C	109.5
H2B—C2—H2C	109.5	H11B—C11—H11C	109.5
C5—C3—N1	106.9 (3)	C10—C12—N4	106.7 (3)
C5—C3—C4	131.0 (4)	C10—C12—C13	130.6 (3)
N1—C3—C4	122.1 (3)	N4—C12—C13	122.7 (3)
C3—C4—H4A	109.5	C12—C13—H13A	109.5
C3—C4—H4B	109.5	C12—C13—H13B	109.5
H4A—C4—H4B	109.5	H13A—C13—H13B	109.5
C3—C4—H4C	109.5	C12—C13—H13C	109.5
H4A—C4—H4C	109.5	H13A—C13—H13C	109.5
H4B—C4—H4C	109.5	H13B—C13—H13C	109.5
C3—C5—N2	107.1 (3)	N4—C14—H14A	109.5
C3—C5—C6	131.7 (3)	N4—C14—H14B	109.5
N2—C5—C6	121.2 (3)	H14A—C14—H14B	109.5
C5—C6—H6A	109.5	N4—C14—H14C	109.5
C5—C6—H6B	109.5	H14A—C14—H14C	109.5
H6A—C6—H6B	109.5	H14B—C14—H14C	109.5
C5—C6—H6C	109.5

S2—Cu1—S1—C1	−58.01 (14)	C1—N2—C5—C6	−179.5 (3)
Cl1—Cu1—S1—C1	127.70 (13)	C7—N2—C5—C6	2.5 (5)
Cl1—Cu1—S2—C8	−168.08 (12)	C12—N4—C8—N3	0.4 (3)
S1—Cu1—S2—C8	18.26 (13)	C14—N4—C8—N3	−178.3 (3)
C5—N2—C1—N1	−0.3 (3)	C12—N4—C8—S2	−178.0 (2)
C7—N2—C1—N1	177.8 (3)	C14—N4—C8—S2	3.3 (5)
C5—N2—C1—S1	175.2 (2)	C10—N3—C8—N4	−0.4 (3)
C7—N2—C1—S1	−6.7 (5)	C9—N3—C8—N4	−179.6 (3)
C3—N1—C1—N2	−0.1 (4)	C10—N3—C8—S2	177.9 (2)
C2—N1—C1—N2	177.1 (3)	C9—N3—C8—S2	−1.2 (5)
C3—N1—C1—S1	−175.6 (2)	Cu1—S2—C8—N4	−94.7 (3)
C2—N1—C1—S1	1.7 (5)	Cu1—S2—C8—N3	87.3 (3)
Cu1—S1—C1—N2	130.1 (3)	C8—N3—C10—C12	0.3 (4)
Cu1—S1—C1—N1	−55.3 (3)	C9—N3—C10—C12	179.5 (3)
C1—N1—C3—C5	0.5 (4)	C8—N3—C10—C11	−179.0 (3)
C2—N1—C3—C5	−176.7 (3)	C9—N3—C10—C11	0.1 (5)
C1—N1—C3—C4	−179.4 (3)	N3—C10—C12—N4	0.0 (3)
C2—N1—C3—C4	3.4 (5)	C11—C10—C12—N4	179.2 (3)
N1—C3—C5—N2	−0.6 (4)	N3—C10—C12—C13	−177.2 (3)
C4—C3—C5—N2	179.2 (4)	C11—C10—C12—C13	2.1 (6)
N1—C3—C5—C6	179.4 (3)	C8—N4—C12—C10	−0.2 (4)
C4—C3—C5—C6	−0.7 (7)	C14—N4—C12—C10	178.5 (3)
C1—N2—C5—C3	0.6 (4)	C8—N4—C12—C13	177.2 (3)
C7—N2—C5—C3	−177.5 (3)	C14—N4—C12—C13	−4.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···S1	0.98	2.74	3.217 (4)	110
C4—H4B···Cl1ⁱ	0.98	2.75	3.717 (4)	170
C7—H7A···S1	0.98	2.73	3.209 (3)	110
C9—H9A···S2	0.98	2.77	3.211 (4)	108
C11—H11A···Cl1ⁱⁱ	0.98	2.76	3.721 (3)	165
C14—H14B···Cl1ⁱⁱⁱ	0.98	2.80	3.782 (4)	176
C14—H14C···S2	0.98	2.77	3.223 (4)	109

Symmetry codes: (i) −x−1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z−1/2; (iii) −x−1/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···S1	0.98	2.74	3.217 (4)	110
C4—H4B···Cl1ⁱ	0.98	2.75	3.717 (4)	170
C7—H7A···S1	0.98	2.73	3.209 (3)	110
C9—H9A···S2	0.98	2.77	3.211 (4)	108
C11—H11A···Cl1ⁱⁱ	0.98	2.76	3.721 (3)	165
C14—H14B···Cl1ⁱⁱⁱ	0.98	2.80	3.782 (4)	176
C14—H14C···S2	0.98	2.77	3.223 (4)	109

Symmetry codes: (i) −x−1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z−1/2; (iii) −x−1/2, y+1/2, −z+3/2.

References

Bhabak, K. P. & Mugesh, G. (2010). Chem. Eur. J. 16, 1175–1185. Web of Science CrossRef CAS PubMed Google Scholar
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Devillanova, F. A., Verani, G., Battaglia, L. P. & Bonamartini Corradi, A. (1980). Transition Met. Chem. 5, 362–364. CSD CrossRef CAS Web of Science Google Scholar
Kimani, M. M., Bayse, C. A. & Brumaghim, J. L. (2011). Dalton Trans. 40, 3711–3723. Web of Science CSD CrossRef CAS PubMed Google Scholar
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Volume 70| Part 12| December 2014| Pages m397-m398

doi:10.1107/S1600536814024404

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of bis­­[1,3,4,5-tetra­methyl-1H-imidazole-2(3H)-thione-κS]chlorido­copper(I)

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

References

metal-organic compounds

Crystal structure of bis[1,3,4,5-tetramethyl-1H-imidazole-2(3H)-thione-κS]chloridocopper(I)