Diiso­propyl­ammonium (3,6-di­chloro­benzene-1,2-di­thiol­ato)cuprato(III) tetra­hydro­furan monosolvate

Barrio, J.; Delgado, E.; Hernández, D.; Hernández, E.; Perles, J.; Zamora, F.

doi:10.1107/S2414314616018836

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 11| November 2016| x161883

https://doi.org/10.1107/S2414314616018836

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Diisopropylammonium (3,6-dichlorobenzene-1,2-dithiolato)cuprato(III) tetrahydrofuran monosolvate

Jesús Barrio,^a Esther Delgado,^a Diego Hernández,^a Elisa Hernández,^a Josefina Perles ^b ^* and Félix Zamora ^a

^aDepartamento de Química Inorgánica, Universidad Autónoma de Madrid, 28049 Madrid, Spain, and ^bLaboratorio de Difracción de Rayos X de Monocristal, SIdI, Universidad Autónoma de Madrid, 28049 Madrid, Spain
^*Correspondence e-mail: josefina.perles@uam.es

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 November 2016; accepted 24 November 2016; online 29 November 2016)

The asymmetric unit of the title compound, (C₆H₁₆N)[Cu(C₆H₂Cl₂S₂)₂]·C₄H₈O, comprises a [Cu(SC₆H₂Cl₂S)₂]⁻ anion, an [ⁱPr₂NH₂]⁺ cation and a solvent tetrahydrofuran molecule. The Cu^III atom has an almost square-planar CuS₄ coordination environment. In the crystal, the anion and the solvent molecule are linked via N—H⋯O and N—H⋯S hydrogen bonds involving the diisopropylammonium cation. There are no other significant intermolecular interactions present.

Keywords: crystal structure; copper(III) dithiolate; coordination compound; ammonium; hydrogen bonding.

CCDC reference: 1519093

Structure description

In the title compound, Fig. 1, the anion presents a planar geometry with the copper(III) atom located at its center in a almost square planar CuS₄ coordination environment. The S—Cu—S bond angles [S4—Cu1—S2 = 87.85 (3), S4—Cu1—S3 = 92.26 (3), S2—Cu1—S1 = 92.14 (4)° and S3—Cu1—S1 = 88.45 (3) °] slightly deviate from 90°, and the Cu—S bond lengths vary from 2.1722 (9) to 2.1776 (9) Å. These geometrical parameters agree well with those observed in a similar compound containing the same anion but with the methyltriphenylphosphonium cation (Herich et al., 2015 ).

Figure 1
The molecular structure of the title compound, with the atom labelling and displacement ellipsoids drawn at the 50% probability level.

In the crystal, the anion and the solvent molecule are linked via N—H⋯O and N—H⋯S hydrogen bonds involving the cation (Fig. 2 and Table 1). There are no other significant intermolecular interactions present.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1	0.89	2.59	3.417 (3)	156
N1—H1B⋯O1ⁱ	0.89	1.93	2.805 (4)	170
Symmetry code: (i) x, y+1, z.

Figure 2
A view along the b axis of the crystal packing of the title compound, with the N—H⋯O and N—H⋯S hydrogen bonds shown as dashed lines (see Table 1

Synthesis and crystallization

To a solution of 1,2-HSC₆H₂Cl₂SH (74 mg, 0.35 mmol) in CH₃CN (3 ml) was added ⁱPr₂NH (99 µl, 0.70 mmol). After stirring for 5 min, Cu(ClO₄)₂·6H₂O (64 mg, 0.18 mmol) was added, and the reaction mixture was left for 2 h in an open atmosphere. Then the solvent was removed in vacuum, yielding a green solid. Recrystallization of this solid in THF/n-heptane (1:1) at room temperature produced green plate-like crystals of the title compound (yield 110 mg, 93%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	(C₆H₁₆N)[Cu(C₆H₂Cl₂S₂)₂]·C₄H₈O
M_r	656.03
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	17.6487 (8), 8.8259 (3), 18.9730 (8)
β (°)	93.616 (2)
V (Å³)	2949.5 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.40
Crystal size (mm)	0.08 × 0.06 × 0.01

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.90, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	35036, 5305, 3766
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.01
No. of reflections	5305
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), Mercury (Macrae et al., 2008 ), SHELXL2014 (Sheldrick, 2015 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1519093

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616018836/su4095sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018836/su4095Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Diisopropylammonium (3,6-dichlorobenzene-1,2-dithiolato)cuprato(III) tetrahydrofuran monosolvate top

Crystal data top

(C₆H₁₆N)[Cu(C₆H₂Cl₂S₂)₂]·C₄H₈O	F(000) = 1344
M_r = 656.03	D_x = 1.477 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.6487 (8) Å	Cell parameters from 7896 reflections
b = 8.8259 (3) Å	θ = 2.6–22.7°
c = 18.9730 (8) Å	µ = 1.40 mm⁻¹
β = 93.616 (2)°	T = 296 K
V = 2949.5 (2) Å³	Plate, green
Z = 4	0.08 × 0.06 × 0.01 mm

Data collection top

Bruker Kappa APEXII diffractometer	5305 independent reflections
Radiation source: fine-focus sealed tube	3766 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
φ and ω scans	θ_max = 25.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→21
T_min = 0.90, T_max = 0.99	k = −10→10
35036 measured reflections	l = −22→22

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0456P)² + 1.2611P] where P = (F_o² + 2F_c²)/3
5305 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	0.89102 (17)	0.7458 (3)	0.7206 (2)	0.0564 (9)
C2	0.9492 (2)	0.8280 (4)	0.6920 (2)	0.0753 (11)
C3	1.0060 (2)	0.8945 (5)	0.7352 (3)	0.0984 (16)
H3	1.0448	0.9482	0.7155	0.118*
C4	1.0048 (3)	0.8807 (5)	0.8072 (3)	0.0986 (15)
H4	1.0431	0.9247	0.8363	0.118*
C5	0.9480 (2)	0.8031 (4)	0.8363 (2)	0.0750 (11)
C6	0.88941 (18)	0.7351 (4)	0.7939 (2)	0.0589 (9)
C7	0.59589 (16)	0.3943 (3)	0.68861 (15)	0.0420 (7)
C8	0.53460 (19)	0.3371 (3)	0.64767 (16)	0.0502 (8)
C9	0.4777 (2)	0.2576 (4)	0.67669 (19)	0.0642 (9)
H9	0.4372	0.2201	0.6481	0.077*
C10	0.4808 (2)	0.2336 (4)	0.74827 (19)	0.0621 (9)
H10	0.4422	0.1804	0.7685	0.074*
C11	0.54128 (18)	0.2887 (3)	0.78993 (16)	0.0510 (8)
C12	0.59981 (17)	0.3693 (3)	0.76139 (15)	0.0423 (7)
C13	0.8609 (2)	0.1804 (6)	0.4692 (3)	0.1000 (15)
H13A	0.8667	0.0854	0.4445	0.12*
H13B	0.9031	0.192	0.5041	0.12*
C14	0.8583 (4)	0.3070 (7)	0.4197 (4)	0.157 (3)
H14A	0.8526	0.2701	0.3715	0.188*
H14B	0.9048	0.3656	0.4252	0.188*
C15	0.7938 (4)	0.4001 (7)	0.4353 (4)	0.155 (3)
H15A	0.8108	0.4976	0.4539	0.186*
H15B	0.7613	0.4169	0.3929	0.186*
C16	0.7545 (3)	0.3222 (7)	0.4853 (3)	0.132 (2)
H16A	0.7029	0.3029	0.4669	0.158*
H16B	0.7524	0.3832	0.5277	0.158*
C18	0.7984 (3)	1.1396 (5)	0.6879 (3)	0.1110 (17)
H18A	0.7897	1.2171	0.7219	0.167*
H18B	0.8244	1.1822	0.6496	0.167*
H18C	0.8289	1.0606	0.7099	0.167*
C17	0.7231 (3)	1.0744 (4)	0.6598 (2)	0.0843 (13)
H17	0.6909	1.1586	0.6423	0.101*
C20	0.6724 (2)	0.8859 (4)	0.5608 (2)	0.0758 (11)
H20	0.6518	0.8159	0.5949	0.091*
C21	0.7039 (3)	0.7943 (6)	0.5022 (2)	0.1007 (14)
H21A	0.6656	0.7257	0.4831	0.151*
H21B	0.7472	0.7377	0.5205	0.151*
H21C	0.7187	0.8612	0.4656	0.151*
C22	0.6102 (3)	0.9937 (6)	0.5353 (3)	0.124 (2)
H22A	0.6308	1.069	0.5053	0.186*
H22B	0.5895	1.0422	0.575	0.186*
H22C	0.5709	0.9385	0.5091	0.186*
C19	0.6817 (4)	0.9914 (5)	0.7149 (3)	0.126 (2)
H19A	0.711	0.9052	0.7311	0.188*
H19B	0.6332	0.9582	0.6948	0.188*
H19C	0.6744	1.0579	0.7539	0.188*
Cl1	0.94808 (7)	0.85050 (15)	0.60108 (7)	0.1084 (4)
Cl2	0.94720 (7)	0.78663 (15)	0.92707 (7)	0.1069 (4)
Cl3	0.52868 (6)	0.36943 (11)	0.55714 (4)	0.0730 (3)
Cl4	0.54440 (6)	0.25575 (13)	0.88029 (5)	0.0835 (3)
Cu1	0.74529 (2)	0.55730 (4)	0.74061 (2)	0.04436 (13)
O1	0.79163 (18)	0.1828 (4)	0.50199 (17)	0.0995 (9)
N1	0.73755 (17)	0.9730 (3)	0.59786 (16)	0.0690 (8)
H1A	0.7725	0.9057	0.6127	0.083*
H1B	0.7581	1.0301	0.5655	0.083*
S1	0.82175 (5)	0.65214 (10)	0.66643 (5)	0.0550 (2)
S2	0.81555 (5)	0.63846 (11)	0.83102 (5)	0.0665 (3)
S3	0.66744 (5)	0.49927 (9)	0.65116 (4)	0.0492 (2)
S4	0.67634 (5)	0.44055 (10)	0.81442 (4)	0.0532 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0364 (18)	0.0413 (17)	0.092 (3)	0.0076 (15)	0.0108 (18)	0.0084 (17)
C2	0.048 (2)	0.061 (2)	0.119 (3)	−0.0013 (19)	0.021 (2)	0.018 (2)
C3	0.050 (3)	0.066 (3)	0.180 (5)	−0.019 (2)	0.017 (3)	0.010 (3)
C4	0.062 (3)	0.073 (3)	0.157 (5)	−0.019 (2)	−0.016 (3)	0.000 (3)
C5	0.055 (2)	0.058 (2)	0.110 (3)	−0.0029 (19)	−0.015 (2)	−0.002 (2)
C6	0.0426 (19)	0.0451 (18)	0.088 (3)	0.0062 (15)	−0.0024 (18)	0.0076 (18)
C7	0.0436 (18)	0.0339 (15)	0.0491 (17)	0.0028 (13)	0.0078 (14)	0.0006 (13)
C8	0.059 (2)	0.0433 (17)	0.0477 (18)	−0.0022 (16)	−0.0002 (16)	0.0007 (14)
C9	0.061 (2)	0.061 (2)	0.069 (2)	−0.0160 (19)	−0.0061 (19)	−0.0033 (18)
C10	0.060 (2)	0.057 (2)	0.070 (2)	−0.0204 (18)	0.0080 (19)	0.0032 (17)
C11	0.056 (2)	0.0490 (18)	0.0484 (18)	−0.0068 (16)	0.0085 (16)	0.0020 (14)
C12	0.0450 (18)	0.0367 (15)	0.0457 (17)	−0.0003 (14)	0.0070 (14)	0.0033 (13)
C13	0.063 (3)	0.105 (4)	0.134 (4)	−0.004 (3)	0.020 (3)	−0.003 (3)
C14	0.149 (6)	0.119 (5)	0.214 (7)	0.022 (4)	0.099 (5)	0.051 (5)
C15	0.146 (6)	0.099 (4)	0.231 (8)	0.024 (4)	0.094 (6)	0.049 (5)
C16	0.142 (5)	0.113 (4)	0.148 (5)	0.040 (4)	0.073 (4)	0.031 (4)
C18	0.135 (5)	0.084 (3)	0.112 (4)	0.030 (3)	−0.009 (3)	−0.019 (3)
C17	0.100 (3)	0.053 (2)	0.101 (3)	0.028 (2)	0.018 (3)	0.004 (2)
C20	0.069 (3)	0.064 (2)	0.094 (3)	0.005 (2)	0.002 (2)	0.024 (2)
C21	0.113 (4)	0.111 (4)	0.077 (3)	0.010 (3)	−0.008 (3)	−0.005 (3)
C22	0.076 (3)	0.106 (4)	0.187 (6)	0.011 (3)	−0.017 (3)	0.054 (4)
C19	0.187 (6)	0.080 (3)	0.118 (4)	0.036 (4)	0.079 (4)	0.011 (3)
Cl1	0.0833 (8)	0.1147 (10)	0.1327 (10)	−0.0095 (7)	0.0513 (7)	0.0343 (8)
Cl2	0.0963 (8)	0.1068 (9)	0.1116 (9)	−0.0110 (7)	−0.0393 (7)	−0.0080 (7)
Cl3	0.0935 (7)	0.0751 (6)	0.0486 (5)	−0.0089 (5)	−0.0093 (5)	0.0011 (4)
Cl4	0.0905 (7)	0.1071 (8)	0.0540 (5)	−0.0341 (6)	0.0134 (5)	0.0160 (5)
Cu1	0.0377 (2)	0.0421 (2)	0.0538 (2)	0.00205 (16)	0.00665 (17)	0.00594 (17)
O1	0.092 (2)	0.095 (2)	0.115 (2)	0.0046 (18)	0.0376 (19)	0.0226 (19)
N1	0.068 (2)	0.0602 (18)	0.080 (2)	0.0217 (16)	0.0127 (17)	0.0166 (16)
S1	0.0422 (5)	0.0579 (5)	0.0659 (5)	0.0026 (4)	0.0123 (4)	0.0120 (4)
S2	0.0565 (6)	0.0795 (7)	0.0627 (5)	−0.0151 (5)	−0.0021 (4)	0.0062 (5)
S3	0.0528 (5)	0.0506 (4)	0.0449 (4)	−0.0043 (4)	0.0097 (4)	0.0058 (4)
S4	0.0493 (5)	0.0640 (5)	0.0460 (4)	−0.0095 (4)	0.0012 (4)	0.0089 (4)

Geometric parameters (Å, º) top

C1—C2	1.394 (5)	C15—H15A	0.97
C1—C6	1.397 (5)	C15—H15B	0.97
C1—S1	1.753 (4)	C16—O1	1.420 (6)
C2—C3	1.384 (6)	C16—H16A	0.97
C2—Cl1	1.736 (4)	C16—H16B	0.97
C3—C4	1.373 (7)	C18—C17	1.514 (6)
C3—H3	0.93	C18—H18A	0.96
C4—C5	1.360 (6)	C18—H18B	0.96
C4—H4	0.93	C18—H18C	0.96
C5—C6	1.404 (5)	C17—C19	1.503 (6)
C5—Cl2	1.729 (5)	C17—N1	1.512 (5)
C6—S2	1.743 (3)	C17—H17	0.98
C7—C8	1.387 (4)	C20—C22	1.509 (5)
C7—C12	1.396 (4)	C20—C21	1.509 (6)
C7—S3	1.752 (3)	C20—N1	1.518 (5)
C8—C9	1.369 (4)	C20—H20	0.98
C8—Cl3	1.738 (3)	C21—H21A	0.96
C9—C10	1.372 (5)	C21—H21B	0.96
C9—H9	0.93	C21—H21C	0.96
C10—C11	1.377 (4)	C22—H22A	0.96
C10—H10	0.93	C22—H22B	0.96
C11—C12	1.392 (4)	C22—H22C	0.96
C11—Cl4	1.736 (3)	C19—H19A	0.96
C12—S4	1.749 (3)	C19—H19B	0.96
C13—O1	1.406 (5)	C19—H19C	0.96
C13—C14	1.459 (7)	Cu1—S4	2.1722 (9)
C13—H13A	0.97	Cu1—S2	2.1736 (10)
C13—H13B	0.97	Cu1—S3	2.1763 (9)
C14—C15	1.450 (7)	Cu1—S1	2.1776 (9)
C14—H14A	0.97	N1—H1A	0.89
C14—H14B	0.97	N1—H1B	0.89
C15—C16	1.391 (7)

C2—C1—C6	118.9 (3)	C15—C16—H16B	109.7
C2—C1—S1	121.4 (3)	O1—C16—H16B	109.7
C6—C1—S1	119.6 (2)	H16A—C16—H16B	108.2
C3—C2—C1	121.0 (4)	C17—C18—H18A	109.5
C3—C2—Cl1	120.1 (3)	C17—C18—H18B	109.5
C1—C2—Cl1	118.9 (3)	H18A—C18—H18B	109.5
C2—C3—C4	119.6 (4)	C17—C18—H18C	109.5
C2—C3—H3	120.2	H18A—C18—H18C	109.5
C4—C3—H3	120.2	H18B—C18—H18C	109.5
C5—C4—C3	120.5 (4)	C19—C17—N1	111.4 (3)
C5—C4—H4	119.8	C19—C17—C18	113.3 (5)
C3—C4—H4	119.8	N1—C17—C18	108.1 (3)
C4—C5—C6	121.2 (4)	C19—C17—H17	108.0
C4—C5—Cl2	120.0 (4)	N1—C17—H17	108.0
C6—C5—Cl2	118.9 (3)	C18—C17—H17	108.0
C5—C6—C1	118.8 (3)	C22—C20—C21	113.2 (4)
C5—C6—S2	121.3 (3)	C22—C20—N1	110.1 (3)
C1—C6—S2	119.9 (3)	C21—C20—N1	108.0 (3)
C8—C7—C12	119.0 (3)	C22—C20—H20	108.5
C8—C7—S3	121.5 (2)	C21—C20—H20	108.5
C12—C7—S3	119.5 (2)	N1—C20—H20	108.5
C9—C8—C7	121.9 (3)	C20—C21—H21A	109.5
C9—C8—Cl3	118.8 (3)	C20—C21—H21B	109.5
C7—C8—Cl3	119.3 (2)	H21A—C21—H21B	109.5
C8—C9—C10	119.5 (3)	C20—C21—H21C	109.5
C8—C9—H9	120.2	H21A—C21—H21C	109.5
C10—C9—H9	120.2	H21B—C21—H21C	109.5
C9—C10—C11	119.6 (3)	C20—C22—H22A	109.5
C9—C10—H10	120.2	C20—C22—H22B	109.5
C11—C10—H10	120.2	H22A—C22—H22B	109.5
C10—C11—C12	121.7 (3)	C20—C22—H22C	109.5
C10—C11—Cl4	118.9 (2)	H22A—C22—H22C	109.5
C12—C11—Cl4	119.4 (2)	H22B—C22—H22C	109.5
C11—C12—C7	118.3 (3)	C17—C19—H19A	109.5
C11—C12—S4	121.7 (2)	C17—C19—H19B	109.5
C7—C12—S4	120.0 (2)	H19A—C19—H19B	109.5
O1—C13—C14	106.3 (4)	C17—C19—H19C	109.5
O1—C13—H13A	110.5	H19A—C19—H19C	109.5
C14—C13—H13A	110.5	H19B—C19—H19C	109.5
O1—C13—H13B	110.5	S4—Cu1—S2	87.85 (3)
C14—C13—H13B	110.5	S4—Cu1—S3	92.26 (3)
H13A—C13—H13B	108.7	S2—Cu1—S3	173.53 (4)
C13—C14—C15	107.1 (5)	S4—Cu1—S1	173.81 (4)
C13—C14—H14A	110.3	S2—Cu1—S1	92.14 (4)
C15—C14—H14A	110.3	S3—Cu1—S1	88.45 (3)
C13—C14—H14B	110.3	C13—O1—C16	108.5 (4)
C15—C14—H14B	110.3	C17—N1—C20	120.0 (3)
H14A—C14—H14B	108.5	C17—N1—H1A	107.3
C16—C15—C14	107.0 (5)	C20—N1—H1A	107.3
C16—C15—H15A	110.3	C17—N1—H1B	107.3
C14—C15—H15A	110.3	C20—N1—H1B	107.3
C16—C15—H15B	110.3	H1A—N1—H1B	106.9
C14—C15—H15B	110.3	C1—S1—Cu1	103.90 (12)
H15A—C15—H15B	108.6	C6—S2—Cu1	104.27 (13)
C15—C16—O1	109.7 (4)	C7—S3—Cu1	104.12 (10)
C15—C16—H16A	109.7	C12—S4—Cu1	104.08 (10)
O1—C16—H16A	109.7

C6—C1—C2—C3	2.0 (5)	C10—C11—C12—C7	0.3 (5)
S1—C1—C2—C3	−176.4 (3)	Cl4—C11—C12—C7	−179.9 (2)
C6—C1—C2—Cl1	−176.3 (3)	C10—C11—C12—S4	179.5 (3)
S1—C1—C2—Cl1	5.3 (4)	Cl4—C11—C12—S4	−0.7 (4)
C1—C2—C3—C4	−0.7 (7)	C8—C7—C12—C11	−0.6 (4)
Cl1—C2—C3—C4	177.6 (4)	S3—C7—C12—C11	178.5 (2)
C2—C3—C4—C5	−0.4 (7)	C8—C7—C12—S4	−179.9 (2)
C3—C4—C5—C6	0.2 (7)	S3—C7—C12—S4	−0.8 (3)
C3—C4—C5—Cl2	180.0 (4)	O1—C13—C14—C15	11.8 (7)
C4—C5—C6—C1	1.2 (5)	C13—C14—C15—C16	−7.2 (9)
Cl2—C5—C6—C1	−178.6 (3)	C14—C15—C16—O1	−0.1 (8)
C4—C5—C6—S2	−178.8 (3)	C14—C13—O1—C16	−11.9 (6)
Cl2—C5—C6—S2	1.3 (4)	C15—C16—O1—C13	7.7 (7)
C2—C1—C6—C5	−2.2 (5)	C19—C17—N1—C20	52.1 (5)
S1—C1—C6—C5	176.2 (2)	C18—C17—N1—C20	177.2 (3)
C2—C1—C6—S2	177.8 (2)	C22—C20—N1—C17	56.5 (5)
S1—C1—C6—S2	−3.8 (4)	C21—C20—N1—C17	−179.5 (3)
C12—C7—C8—C9	0.4 (5)	C2—C1—S1—Cu1	−177.0 (2)
S3—C7—C8—C9	−178.7 (2)	C6—C1—S1—Cu1	4.6 (3)
C12—C7—C8—Cl3	179.3 (2)	C5—C6—S2—Cu1	−179.1 (3)
S3—C7—C8—Cl3	0.2 (4)	C1—C6—S2—Cu1	0.8 (3)
C7—C8—C9—C10	0.1 (5)	C8—C7—S3—Cu1	179.6 (2)
Cl3—C8—C9—C10	−178.8 (3)	C12—C7—S3—Cu1	0.5 (2)
C8—C9—C10—C11	−0.5 (5)	C11—C12—S4—Cu1	−178.7 (2)
C9—C10—C11—C12	0.3 (5)	C7—C12—S4—Cu1	0.6 (3)
C9—C10—C11—Cl4	−179.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1	0.89	2.59	3.417 (3)	156
N1—H1B···O1ⁱ	0.89	1.93	2.805 (4)	170

Symmetry code: (i) x, y+1, z.

References

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