Copper(I) iodide ribbons coordinated with thio­urea derivatives

Two products of the reactions of CuI with 1-benzoyl-3-(4-bromo­phen­yl)thio­urea and with 1-benzoyl-3-(2-iodo­phen­yl)thio­urea have been obtained and characterized, namely poly[[[1-benzoyl-3-(4-bromo­phen­yl)thio­urea-κS]-μ₃-iodido-copper(I)] acetone hemisolvate], {[CuI(C₁₄H₁₁BrN₂OS)]·0.5C₃H₆O}_n, and poly[μ₄-iodido-μ₃-iodido-[N-(benzo[d]thia­zol-2-yl)benzamide-κN]dicopper(I)], [Cu₂I₂(C₁₄H₁₀N₂OS)]_n. Their structures, determined by single-crystal X-ray diffraction analysis, exhibit different stoichiometries and mol­ecular organizations; however, both compounds are polymeric and possess close Cu...Cu contacts. The first product contains a (CuI)_n double chain supported by the thio­urea derivative coordinated via the S atom. In the second case, the ligand undergoes dehalogenation and cyclization to form N-(benzo[d]thia­zol-2-yl)benzamide that serves as the N-donor ligand which is connected to both sides of a (CuI)_n quadruple chain. In both hybrid inorganic chains, I atoms bridge three or four Cu atoms. The coordination centres adopt more or less distorted tetra­hedral geometries. The structures of the (CuI)_n kernels of the ribbons are similar to fragments of the layers in high-pressure phase V copper(I) iodide. Only weak S...O, C—H...O, C—H...I and π–π inter­actions hold the ribbons together, allowing the formation of crystals.

Computing details

For both structures, data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[[1-benzoyl-3-(4-bromophenyl)thiourea-κS]-µ₃-iodido-copper(I)] acetone hemisolvate] (I)

Crystal data

[CuBrI(C14H11N2OS)]·0.5C3H6O	Z = 2
Mr = 554.70	F(000) = 532
Triclinic, P1	Dx = 2.073 Mg m^−3
a = 4.0594 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8684 (8) Å	Cell parameters from 6948 reflections
c = 20.7336 (15) Å	θ = 2.5–29.5°
α = 102.079 (6)°	µ = 5.34 mm^−1
β = 94.047 (6)°	T = 120 K
γ = 94.299 (6)°	Needle, colourless
V = 888.48 (11) Å^3	0.44 × 0.02 × 0.02 mm

Data collection

Stoe IPDS 2T diffractometer	3446 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2	3069 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromator	Rint = 0.048
rotation method scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), by Gaussian integration, analogous to Coppens (1970)]	h = −4→5
Tmin = 0.358, Tmax = 0.905	k = −12→13
7687 measured reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.175	w = 1/[σ^2(Fo^2) + (0.1209P)^2 + 2.3538P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3446 reflections	Δρmax = 1.89 e Å^−3
257 parameters	Δρmin = −2.96 e Å^−3
40 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.7353 (2)	0.50967 (9)	0.45015 (4)	0.0367 (3)	0.900 (2)
I1	0.72245 (10)	0.32964 (4)	0.51899 (2)	0.0331 (2)	0.900 (2)
Br1	0.3217 (2)	−0.09639 (9)	0.07159 (5)	0.0580 (3)	0.900 (2)
S1	0.6415 (5)	0.39525 (19)	0.34375 (9)	0.0395 (4)	0.900 (2)
Cu1A	0.785 (4)	0.6685 (15)	0.4747 (8)	0.029 (4)*	0.0453 (18)
I1A	0.776 (3)	0.4872 (10)	0.5400 (5)	0.038 (3)*	0.0453 (18)
Br1A	0.338 (15)	0.041 (6)	0.078 (3)	0.151 (18)*	0.0453 (18)
S1A	0.68 (2)	0.558 (9)	0.364 (5)	0.10 (2)*	0.0453 (18)
Cu1B	0.678 (5)	0.351 (2)	0.4294 (10)	0.060 (5)*	0.0551 (18)
I1B	0.666 (3)	0.1721 (12)	0.4984 (6)	0.062 (3)*	0.0551 (18)
Br1B	0.250 (3)	−0.2533 (12)	0.0517 (6)	0.038 (3)*	0.0551 (18)
S1B	0.583 (9)	0.241 (3)	0.3243 (18)	0.047 (8)*	0.0551 (18)
N1	0.8582 (17)	0.6097 (6)	0.3122 (3)	0.0463 (14)
H1	0.860628	0.638312	0.355249	0.056*
N2	0.7669 (19)	0.4367 (7)	0.2243 (3)	0.0522 (16)
H2	0.832923	0.490828	0.200671	0.063*
O1	0.967 (2)	0.6685 (6)	0.2156 (3)	0.0693 (19)
C1	0.7634 (19)	0.4798 (8)	0.2899 (3)	0.0437 (16)
C16	0.8901 (19)	0.8737 (7)	0.3752 (4)	0.0448 (16)
H16	0.775127	0.815977	0.396345	0.054*
C23	0.685 (2)	0.0867 (9)	0.1746 (4)	0.0531 (19)
H23	0.762630	0.015384	0.188674	0.064*
C10	0.948 (2)	0.6993 (9)	0.2763 (4)	0.0525 (19)
C15	0.944 (2)	1.0023 (8)	0.4061 (4)	0.0466 (17)
H15	0.858246	1.032465	0.447361	0.056*
C25	0.362 (2)	0.1708 (9)	0.0960 (4)	0.057 (2)
H25	0.220284	0.157117	0.056229	0.068*
C21	0.670 (2)	0.3085 (8)	0.1901 (4)	0.0479 (18)
C11	1.0076 (19)	0.8305 (8)	0.3129 (4)	0.0459 (16)
C22	0.786 (2)	0.2072 (8)	0.2109 (4)	0.0485 (18)
H22	0.933850	0.219393	0.249789	0.058*
C24	0.474 (2)	0.0701 (9)	0.1188 (4)	0.0522 (19)
C12	1.183 (2)	0.9161 (8)	0.2840 (4)	0.0474 (17)
H12	1.264643	0.887651	0.242164	0.057*
C13	1.239 (2)	1.0424 (8)	0.3152 (4)	0.0496 (18)
H13	1.360063	1.099932	0.294903	0.060*
C14	1.120 (2)	1.0847 (8)	0.3762 (4)	0.0484 (17)
H14	1.160847	1.171341	0.397616	0.058*
C26	0.460 (2)	0.2948 (9)	0.1323 (4)	0.056 (2)
H26	0.384693	0.366188	0.117945	0.067*
O1S	−0.072 (7)	0.3846 (16)	0.0058 (12)	0.142 (7)	0.5
C2S	0.030 (5)	0.4885 (15)	0.0000 (8)	0.120 (7)	0.5
C3S	0.060 (9)	0.521 (2)	−0.0666 (9)	0.118 (8)	0.5
H3SA	−0.156737	0.502748	−0.092409	0.177*	0.5
H3SB	0.221112	0.469917	−0.090205	0.177*	0.5
H3SC	0.133864	0.610672	−0.060622	0.177*	0.5
C1S	0.128 (9)	0.5950 (18)	0.0589 (10)	0.120 (8)	0.5
H1SA	0.329045	0.577161	0.083131	0.180*	0.5
H1SB	−0.052060	0.603279	0.088163	0.180*	0.5
H1SC	0.171456	0.673967	0.043958	0.180*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0381 (5)	0.0382 (5)	0.0369 (5)	0.0022 (4)	0.0088 (4)	0.0139 (4)
I1	0.0297 (3)	0.0363 (3)	0.0374 (3)	0.00253 (18)	0.00804 (18)	0.0156 (2)
Br1	0.0554 (6)	0.0520 (6)	0.0599 (6)	−0.0024 (4)	0.0080 (4)	−0.0020 (4)
S1	0.0471 (11)	0.0387 (10)	0.0353 (9)	−0.0027 (8)	0.0116 (7)	0.0132 (7)
N1	0.056 (4)	0.046 (4)	0.038 (3)	−0.001 (3)	0.007 (3)	0.015 (3)
N2	0.063 (4)	0.052 (4)	0.043 (3)	−0.004 (3)	0.015 (3)	0.015 (3)
O1	0.107 (6)	0.058 (4)	0.045 (3)	−0.007 (4)	0.017 (3)	0.021 (3)
C1	0.045 (4)	0.051 (4)	0.036 (3)	−0.002 (3)	0.006 (3)	0.013 (3)
C16	0.046 (4)	0.045 (4)	0.046 (4)	0.000 (3)	0.006 (3)	0.019 (3)
C23	0.056 (5)	0.063 (5)	0.041 (4)	0.001 (4)	0.018 (3)	0.009 (4)
C10	0.059 (5)	0.061 (5)	0.038 (4)	0.002 (4)	0.009 (3)	0.012 (3)
C15	0.048 (4)	0.050 (4)	0.046 (4)	0.009 (3)	0.005 (3)	0.019 (3)
C25	0.054 (5)	0.070 (6)	0.045 (4)	−0.005 (4)	0.008 (3)	0.011 (4)
C21	0.050 (4)	0.052 (5)	0.042 (4)	0.000 (3)	0.015 (3)	0.008 (3)
C11	0.045 (4)	0.047 (4)	0.048 (4)	0.000 (3)	0.003 (3)	0.018 (3)
C22	0.049 (4)	0.061 (5)	0.039 (4)	0.002 (4)	0.011 (3)	0.017 (3)
C24	0.054 (5)	0.058 (5)	0.044 (4)	−0.002 (4)	0.015 (3)	0.007 (4)
C12	0.046 (4)	0.055 (5)	0.043 (4)	0.001 (3)	0.010 (3)	0.016 (3)
C13	0.042 (4)	0.054 (5)	0.059 (5)	0.003 (3)	0.009 (3)	0.025 (4)
C14	0.048 (4)	0.048 (4)	0.053 (4)	0.002 (3)	0.005 (3)	0.018 (3)
C26	0.061 (5)	0.059 (5)	0.047 (4)	0.003 (4)	0.010 (4)	0.012 (4)
O1S	0.173 (18)	0.124 (14)	0.127 (15)	−0.001 (15)	0.022 (14)	0.023 (12)
C2S	0.144 (16)	0.086 (12)	0.158 (15)	0.034 (12)	0.027 (13)	0.078 (11)
C3S	0.15 (2)	0.069 (13)	0.151 (18)	0.020 (14)	0.040 (17)	0.049 (13)
C1S	0.15 (2)	0.098 (14)	0.141 (17)	0.028 (15)	0.020 (16)	0.095 (12)

Geometric parameters (Å, º)

Cu1—Cu1^i	2.9257 (19)	C23—C22	1.384 (12)
Cu1—Cu1^ii	2.9402 (18)	C23—C24	1.362 (13)
Cu1—I1^ii	2.6643 (10)	C10—C11	1.462 (12)
Cu1—I1	2.6520 (10)	C15—H15	0.9500
Cu1—I1^i	2.6576 (11)	C15—C14	1.377 (11)
Cu1—S1	2.285 (2)	C25—H25	0.9500
Br1—C24	1.903 (9)	C25—C24	1.374 (14)
S1—C1	1.666 (7)	C25—C26	1.411 (13)
Cu1A—I1A^ii	2.69 (2)	C21—C22	1.366 (12)
Cu1A—I1A	2.614 (18)	C21—C26	1.398 (12)
Cu1A—I1A^i	2.540 (19)	C11—C12	1.387 (11)
Cu1A—S1A	2.35 (9)	C22—H22	0.9500
I1A—I1A^i	2.59 (2)	C12—H12	0.9500
I1A—I1A^ii	2.76 (2)	C12—C13	1.384 (12)
Cu1B—I1B	2.64 (2)	C13—H13	0.9500
Cu1B—S1B	2.25 (4)	C13—C14	1.386 (12)
N1—H1	0.8800	C14—H14	0.9500
N1—C1	1.405 (10)	C26—H26	0.9500
N1—C10	1.388 (11)	O1S—C2S	1.2070
N2—H2	0.8800	C2S—C3S	1.5042
N2—C1	1.343 (10)	C2S—C1S	1.5040
N2—C21	1.436 (10)	C3S—H3SA	0.9800
O1—C10	1.242 (10)	C3S—H3SB	0.9800
C16—H16	0.9500	C3S—H3SC	0.9800
C16—C15	1.404 (11)	C1S—H1SA	0.9800
C16—C11	1.408 (11)	C1S—H1SB	0.9800
C23—H23	0.9500	C1S—H1SC	0.9800
Cu1^i—Cu1—Cu1^ii	87.58 (5)	C14—C15—C16	119.8 (7)
I1—Cu1—Cu1^i	56.65 (3)	C14—C15—H15	120.1
I1^i—Cu1—Cu1^ii	120.17 (5)	C24—C25—H25	120.3
I1^ii—Cu1—Cu1^ii	56.22 (3)	C24—C25—C26	119.4 (8)
I1^i—Cu1—Cu1^i	56.47 (3)	C26—C25—H25	120.3
I1^ii—Cu1—Cu1^i	120.04 (5)	C22—C21—N2	122.7 (7)
I1—Cu1—Cu1^ii	56.62 (3)	C22—C21—C26	122.2 (8)
I1—Cu1—I1^i	113.12 (4)	C26—C21—N2	115.1 (8)
I1—Cu1—I1^ii	112.84 (3)	C16—C11—C10	123.0 (7)
I1^i—Cu1—I1^ii	99.42 (3)	C12—C11—C16	119.0 (7)
S1—Cu1—Cu1^ii	121.97 (7)	C12—C11—C10	118.0 (7)
S1—Cu1—Cu1^i	127.74 (8)	C23—C22—H22	120.4
S1—Cu1—I1^i	117.82 (6)	C21—C22—C23	119.1 (8)
S1—Cu1—I1^ii	112.19 (7)	C21—C22—H22	120.4
S1—Cu1—I1	101.98 (6)	C23—C24—Br1	119.6 (7)
Cu1^i—I1—Cu1^ii	99.42 (3)	C23—C24—C25	121.7 (9)
Cu1—I1—Cu1^i	66.88 (4)	C25—C24—Br1	118.7 (7)
Cu1—I1—Cu1^ii	67.15 (3)	C11—C12—H12	119.6
C1—S1—Cu1	111.3 (3)	C13—C12—C11	120.9 (7)
I1A^i—Cu1A—I1A	60.3 (5)	C13—C12—H12	119.6
S1A—Cu1A—I1A^i	76 (2)	C12—C13—H13	120.0
S1A—Cu1A—I1A	103 (2)	C12—C13—C14	119.9 (8)
Cu1A^i—I1A—Cu1A	119.7 (5)	C14—C13—H13	120.0
Cu1A^i—I1A—I1A^i	61.3 (6)	C15—C14—C13	120.6 (8)
I1A^i—I1A—Cu1A	58.4 (5)	C15—C14—H14	119.7
S1B—Cu1B—I1B	102.9 (13)	C13—C14—H14	119.7
C1—N1—H1	115.3	C25—C26—H26	121.3
C10—N1—H1	115.3	C21—C26—C25	117.5 (9)
C10—N1—C1	129.4 (6)	C21—C26—H26	121.3
C1—N2—H2	117.7	O1S—C2S—C3S	122.2
C1—N2—C21	124.6 (7)	O1S—C2S—C1S	122.0
C21—N2—H2	117.7	C1S—C2S—C3S	115.8
N1—C1—S1	119.3 (5)	C2S—C3S—H3SA	109.5
N2—C1—S1	125.9 (6)	C2S—C3S—H3SB	109.5
N2—C1—N1	114.7 (7)	C2S—C3S—H3SC	109.5
C15—C16—H16	120.1	H3SA—C3S—H3SB	109.5
C15—C16—C11	119.7 (7)	H3SA—C3S—H3SC	109.5
C11—C16—H16	120.1	H3SB—C3S—H3SC	109.5
C22—C23—H23	120.0	C2S—C1S—H1SA	109.5
C24—C23—H23	120.0	C2S—C1S—H1SB	109.5
C24—C23—C22	120.1 (9)	C2S—C1S—H1SC	109.5
N1—C10—C11	116.8 (7)	H1SA—C1S—H1SB	109.5
O1—C10—N1	120.8 (8)	H1SA—C1S—H1SC	109.5
O1—C10—C11	122.3 (8)	H1SB—C1S—H1SC	109.5
C16—C15—H15	120.1
Cu1—S1—C1—N1	−9.1 (7)	C10—C11—C12—C13	178.3 (8)
Cu1—S1—C1—N2	174.3 (6)	C15—C16—C11—C10	−177.1 (8)
N1—C10—C11—C16	−18.5 (12)	C15—C16—C11—C12	1.7 (11)
N1—C10—C11—C12	162.6 (8)	C21—N2—C1—S1	−1.2 (12)
N2—C21—C22—C23	−179.0 (7)	C21—N2—C1—N1	−178.1 (7)
N2—C21—C26—C25	178.8 (7)	C11—C16—C15—C14	−2.2 (12)
O1—C10—C11—C16	159.2 (9)	C11—C12—C13—C14	−0.1 (12)
O1—C10—C11—C12	−19.6 (13)	C22—C23—C24—Br1	−177.2 (6)
C1—N1—C10—O1	−2.9 (15)	C22—C23—C24—C25	1.5 (13)
C1—N1—C10—C11	174.8 (8)	C22—C21—C26—C25	1.3 (12)
C1—N2—C21—C22	−48.9 (12)	C24—C23—C22—C21	0.3 (12)
C1—N2—C21—C26	133.6 (9)	C24—C25—C26—C21	0.5 (12)
C16—C15—C14—C13	1.5 (12)	C12—C13—C14—C15	−0.3 (12)
C16—C11—C12—C13	−0.6 (12)	C26—C25—C24—Br1	176.8 (6)
C10—N1—C1—S1	−175.8 (7)	C26—C25—C24—C23	−1.9 (13)
C10—N1—C1—N2	1.2 (12)	C26—C21—C22—C23	−1.7 (12)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1^i	0.88	2.95	3.688 (6)	143
N2—H2···O1	0.88	1.92	2.635 (10)	137

Symmetry code: (i) −x+2, −y+1, −z+1.

Poly[µ₄-iodido-µ₃-iodido-[N-(benzo[d]thiazol-2-yl)benzamide-κN]dicopper(I)] (II)

Crystal data

[Cu2I2(C14H10N2OS)]	F(000) = 592
Mr = 635.18	Dx = 2.583 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 12.6880 (12) Å	Cell parameters from 1069 reflections
b = 4.1152 (4) Å	θ = 2.9–29.4°
c = 15.8952 (15) Å	µ = 6.51 mm^−1
β = 100.258 (8)°	T = 120 K
V = 816.68 (14) Å^3	Needle, brown
Z = 2	0.57 × 0.09 × 0.06 mm

Data collection

Stoe IPDS 2T diffractometer	3163 independent reflections
Radiation source: microfocus sealed X-ray tube, GeniX Mo, 0.05 x 0.05 mm2	3139 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromator	Rint = 0.039
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.6°
rotation method scans	h = −15→15
Absorption correction: integration [X-RED32 (Stoe & Cie, 2009), by Gaussian integration, analogous to Coppens (1970)]	k = −4→5
Tmin = 0.175, Tmax = 0.688	l = −19→19
7646 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0771P)^2 + 6.6934P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.121	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 1.31 e Å^−3
3163 reflections	Δρmin = −2.03 e Å^−3
199 parameters	Absolute structure: Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.11 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I2	1.02099 (5)	0.89173 (17)	0.37962 (5)	0.0200 (2)
I1	0.72945 (6)	0.48198 (19)	0.41104 (5)	0.0220 (2)
Cu2	0.93650 (12)	0.3849 (4)	0.45145 (10)	0.0270 (4)
Cu1	0.81130 (14)	−0.0090 (5)	0.33639 (12)	0.0373 (4)
S1	0.6135 (2)	0.1705 (8)	0.07118 (19)	0.0233 (6)
O1	0.4394 (7)	−0.107 (3)	0.1140 (5)	0.031 (2)
N1	0.5840 (8)	−0.123 (3)	0.2190 (6)	0.024 (2)
H1	0.609540	−0.193974	0.270900	0.028*
N2	0.7534 (8)	0.087 (3)	0.2105 (6)	0.021 (2)
C1	0.6534 (9)	0.030 (3)	0.1759 (7)	0.020 (2)
C25	0.9109 (9)	0.371 (4)	0.1740 (7)	0.024 (2)
H25	0.953311	0.330248	0.228530	0.029*
C21	0.7436 (10)	0.325 (3)	0.0755 (8)	0.023 (2)
C22	0.7821 (9)	0.498 (4)	0.0125 (8)	0.026 (3)
H22	0.737748	0.543116	−0.040998	0.031*
C13	0.2541 (10)	−0.612 (4)	0.2674 (9)	0.036 (3)
H13	0.190294	−0.725404	0.243961	0.044*
C10	0.4763 (10)	−0.176 (4)	0.1874 (8)	0.026 (3)
C24	0.9525 (10)	0.544 (4)	0.1116 (8)	0.027 (3)
H24	1.024029	0.622134	0.123787	0.033*
C14	0.2820 (11)	−0.581 (4)	0.3551 (9)	0.037 (3)
H14	0.238052	−0.671896	0.391680	0.044*
C20	0.8073 (9)	0.263 (3)	0.1545 (7)	0.021 (2)
C11	0.4125 (9)	−0.319 (3)	0.2479 (8)	0.025 (3)
C12	0.3176 (10)	−0.481 (4)	0.2121 (10)	0.033 (3)
H12	0.297025	−0.501082	0.151884	0.040*
C23	0.8890 (10)	0.604 (4)	0.0305 (9)	0.029 (3)
H23	0.918855	0.715912	−0.011950	0.035*
C15	0.3770 (10)	−0.413 (4)	0.3895 (8)	0.033 (3)
H15	0.396217	−0.386533	0.449633	0.040*
C16	0.4414 (10)	−0.287 (4)	0.3374 (8)	0.028 (3)
H16	0.505710	−0.177906	0.361500	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I2	0.0181 (3)	0.0203 (4)	0.0216 (4)	0.0004 (3)	0.0039 (3)	0.0007 (3)
I1	0.0204 (4)	0.0224 (4)	0.0231 (4)	0.0016 (3)	0.0034 (3)	0.0030 (3)
Cu2	0.0247 (7)	0.0292 (9)	0.0271 (7)	−0.0026 (7)	0.0049 (6)	−0.0040 (7)
Cu1	0.0349 (8)	0.0414 (11)	0.0348 (9)	−0.0009 (9)	0.0046 (7)	0.0011 (9)
S1	0.0187 (13)	0.0324 (17)	0.0183 (13)	0.0016 (12)	0.0019 (10)	0.0030 (12)
O1	0.026 (4)	0.047 (6)	0.020 (4)	0.001 (5)	0.002 (3)	0.005 (5)
N1	0.022 (4)	0.033 (6)	0.016 (4)	0.001 (5)	0.003 (4)	0.003 (5)
N2	0.022 (5)	0.024 (5)	0.017 (5)	0.000 (4)	0.003 (4)	0.004 (4)
C1	0.017 (5)	0.028 (7)	0.014 (5)	0.003 (5)	−0.001 (4)	−0.002 (5)
C25	0.028 (6)	0.025 (6)	0.019 (5)	0.003 (5)	0.004 (4)	−0.002 (5)
C21	0.024 (5)	0.022 (7)	0.025 (6)	0.002 (5)	0.006 (4)	−0.002 (5)
C22	0.021 (5)	0.037 (7)	0.018 (5)	0.002 (6)	−0.001 (4)	0.001 (6)
C13	0.026 (6)	0.039 (8)	0.044 (8)	−0.001 (6)	0.007 (6)	0.005 (7)
C10	0.024 (6)	0.025 (7)	0.029 (6)	0.001 (5)	0.007 (5)	−0.005 (5)
C24	0.024 (6)	0.025 (7)	0.033 (7)	−0.001 (5)	0.008 (5)	−0.007 (6)
C14	0.030 (6)	0.046 (10)	0.038 (7)	0.006 (7)	0.013 (6)	0.015 (7)
C20	0.023 (5)	0.022 (6)	0.020 (6)	0.003 (5)	0.007 (4)	−0.002 (5)
C11	0.021 (5)	0.029 (7)	0.025 (6)	0.004 (5)	0.006 (5)	−0.004 (5)
C12	0.026 (6)	0.030 (7)	0.044 (8)	0.002 (6)	0.008 (6)	0.003 (7)
C23	0.023 (6)	0.035 (8)	0.030 (7)	0.001 (6)	0.006 (5)	0.005 (6)
C15	0.024 (6)	0.050 (9)	0.025 (6)	−0.003 (6)	0.002 (5)	0.003 (6)
C16	0.028 (6)	0.037 (8)	0.019 (6)	0.006 (6)	0.004 (5)	−0.004 (5)

Geometric parameters (Å, º)

I2—Cu2^i	2.6431 (18)	C25—C20	1.370 (17)
I2—Cu2	2.6905 (18)	C21—C22	1.386 (18)
I2—Cu2^ii	2.6473 (18)	C21—C20	1.392 (17)
I2—Cu1^ii	2.658 (2)	C22—H22	0.9500
I1—Cu2	2.6216 (17)	C22—C23	1.406 (17)
I1—Cu1^ii	2.704 (2)	C13—H13	0.9500
I1—Cu1	2.647 (2)	C13—C14	1.38 (2)
Cu2—Cu2^iii	2.885 (2)	C13—C12	1.403 (19)
Cu2—Cu2^i	2.885 (2)	C10—C11	1.485 (17)
Cu2—Cu1	2.732 (2)	C24—H24	0.9500
Cu1—N2	2.044 (10)	C24—C23	1.414 (19)
S1—C1	1.749 (11)	C14—H14	0.9500
S1—C21	1.759 (13)	C14—C15	1.41 (2)
O1—C10	1.210 (16)	C11—C12	1.406 (19)
N1—H1	0.8800	C11—C16	1.411 (17)
N1—C1	1.363 (16)	C12—H12	0.9500
N1—C10	1.387 (15)	C23—H23	0.9500
N2—C1	1.311 (15)	C15—H15	0.9500
N2—C20	1.414 (15)	C15—C16	1.364 (19)
C25—H25	0.9500	C16—H16	0.9500
C25—C24	1.398 (18)
Cu2^i—I2—Cu2^ii	66.11 (5)	C1—N2—C20	111.6 (10)
Cu2^ii—I2—Cu2	100.88 (5)	C20—N2—Cu1	125.8 (8)
Cu2^i—I2—Cu2	65.50 (5)	N1—C1—S1	121.9 (8)
Cu2^i—I2—Cu1^ii	106.14 (6)	N2—C1—S1	115.7 (9)
Cu2^ii—I2—Cu1^ii	61.97 (6)	N2—C1—N1	122.3 (10)
Cu1^ii—I2—Cu2	76.87 (6)	C24—C25—H25	120.9
Cu2—I1—Cu1	62.45 (6)	C20—C25—H25	120.9
Cu2—I1—Cu1^ii	77.24 (6)	C20—C25—C24	118.2 (11)
Cu1—I1—Cu1^ii	100.52 (6)	C22—C21—S1	127.4 (10)
I2^iii—Cu2—I2^iv	114.92 (7)	C22—C21—C20	121.6 (11)
I2^iii—Cu2—I2	113.47 (6)	C20—C21—S1	111.0 (9)
I2^iv—Cu2—I2	100.88 (5)	C21—C22—H22	121.2
I2^iv—Cu2—Cu2^i	123.16 (8)	C21—C22—C23	117.6 (11)
I2^iii—Cu2—Cu2^iii	58.04 (6)	C23—C22—H22	121.2
I2—Cu2—Cu2^i	56.46 (4)	C14—C13—H13	119.2
I2^iii—Cu2—Cu2^i	57.02 (6)	C14—C13—C12	121.6 (14)
I2^iv—Cu2—Cu2^iii	56.88 (4)	C12—C13—H13	119.2
I2—Cu2—Cu2^iii	123.57 (8)	O1—C10—N1	120.0 (12)
I2—Cu2—Cu1	113.83 (7)	O1—C10—C11	123.8 (11)
I2^iv—Cu2—Cu1	59.21 (5)	N1—C10—C11	116.2 (11)
I2^iii—Cu2—Cu1	132.51 (8)	C25—C24—H24	119.7
I1—Cu2—I2	103.62 (6)	C25—C24—C23	120.7 (12)
I1—Cu2—I2^iii	105.17 (6)	C23—C24—H24	119.7
I1—Cu2—I2^iv	118.44 (6)	C13—C14—H14	120.6
I1—Cu2—Cu2^iii	132.81 (7)	C13—C14—C15	118.9 (13)
I1—Cu2—Cu2^i	117.53 (6)	C15—C14—H14	120.6
I1—Cu2—Cu1	59.23 (6)	C25—C20—N2	125.2 (11)
Cu2^iii—Cu2—Cu2^i	90.97 (9)	C25—C20—C21	121.6 (11)
Cu1—Cu2—Cu2^i	169.75 (8)	C21—C20—N2	113.2 (10)
Cu1—Cu2—Cu2^iii	97.92 (5)	C12—C11—C10	116.9 (11)
I2^iv—Cu1—I1^iv	102.26 (7)	C12—C11—C16	120.2 (12)
I2^iv—Cu1—Cu2	58.81 (5)	C16—C11—C10	122.9 (12)
I1—Cu1—I2^iv	117.13 (7)	C13—C12—C11	118.4 (13)
I1—Cu1—I1^iv	100.52 (6)	C13—C12—H12	120.8
I1^iv—Cu1—Cu2	112.88 (7)	C11—C12—H12	120.8
I1—Cu1—Cu2	58.32 (5)	C22—C23—C24	120.3 (12)
N2—Cu1—I2^iv	116.8 (3)	C22—C23—H23	119.9
N2—Cu1—I1^iv	118.7 (3)	C24—C23—H23	119.9
N2—Cu1—I1	100.9 (3)	C14—C15—H15	119.5
N2—Cu1—Cu2	127.3 (3)	C16—C15—C14	120.9 (13)
C1—S1—C21	88.4 (6)	C16—C15—H15	119.5
C1—N1—H1	117.5	C11—C16—H16	120.0
C1—N1—C10	124.9 (10)	C15—C16—C11	120.0 (13)
C10—N1—H1	117.5	C15—C16—H16	120.0
C1—N2—Cu1	121.9 (8)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1^iv	0.88	2.80	3.654 (10)	164

Symmetry code: (iv) x, y−1, z.