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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-κ
S]-μ
3-iodido-copper(I)] acetone hemisolvate], {[CuI(C
14H
11BrN
2OS)]·0.5C
3H
6O}
n, and poly[μ
4-iodido-μ
3-iodido-[
N-(benzo[
d]thiazol-2-yl)benzamide-κ
N]dicopper(I)], [Cu
2I
2(C
14H
10N
2OS)]
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.
Supporting information
CCDC references: 1877164; 1877163
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]-µ
3-iodido-copper(I)]
acetone hemisolvate] (I)
top
Crystal data top
[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) Å3 | 0.44 × 0.02 × 0.02 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.175 | w = 1/[σ2(Fo2) + (0.1209P)2 + 2.3538P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Cu1—Cu1i | 2.9257 (19) | C23—C22 | 1.384 (12) |
Cu1—Cu1ii | 2.9402 (18) | C23—C24 | 1.362 (13) |
Cu1—I1ii | 2.6643 (10) | C10—C11 | 1.462 (12) |
Cu1—I1 | 2.6520 (10) | C15—H15 | 0.9500 |
Cu1—I1i | 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—I1Aii | 2.69 (2) | C21—C22 | 1.366 (12) |
Cu1A—I1A | 2.614 (18) | C21—C26 | 1.398 (12) |
Cu1A—I1Ai | 2.540 (19) | C11—C12 | 1.387 (11) |
Cu1A—S1A | 2.35 (9) | C22—H22 | 0.9500 |
I1A—I1Ai | 2.59 (2) | C12—H12 | 0.9500 |
I1A—I1Aii | 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 |
| | | |
Cu1i—Cu1—Cu1ii | 87.58 (5) | C14—C15—C16 | 119.8 (7) |
I1—Cu1—Cu1i | 56.65 (3) | C14—C15—H15 | 120.1 |
I1i—Cu1—Cu1ii | 120.17 (5) | C24—C25—H25 | 120.3 |
I1ii—Cu1—Cu1ii | 56.22 (3) | C24—C25—C26 | 119.4 (8) |
I1i—Cu1—Cu1i | 56.47 (3) | C26—C25—H25 | 120.3 |
I1ii—Cu1—Cu1i | 120.04 (5) | C22—C21—N2 | 122.7 (7) |
I1—Cu1—Cu1ii | 56.62 (3) | C22—C21—C26 | 122.2 (8) |
I1—Cu1—I1i | 113.12 (4) | C26—C21—N2 | 115.1 (8) |
I1—Cu1—I1ii | 112.84 (3) | C16—C11—C10 | 123.0 (7) |
I1i—Cu1—I1ii | 99.42 (3) | C12—C11—C16 | 119.0 (7) |
S1—Cu1—Cu1ii | 121.97 (7) | C12—C11—C10 | 118.0 (7) |
S1—Cu1—Cu1i | 127.74 (8) | C23—C22—H22 | 120.4 |
S1—Cu1—I1i | 117.82 (6) | C21—C22—C23 | 119.1 (8) |
S1—Cu1—I1ii | 112.19 (7) | C21—C22—H22 | 120.4 |
S1—Cu1—I1 | 101.98 (6) | C23—C24—Br1 | 119.6 (7) |
Cu1i—I1—Cu1ii | 99.42 (3) | C23—C24—C25 | 121.7 (9) |
Cu1—I1—Cu1i | 66.88 (4) | C25—C24—Br1 | 118.7 (7) |
Cu1—I1—Cu1ii | 67.15 (3) | C11—C12—H12 | 119.6 |
C1—S1—Cu1 | 111.3 (3) | C13—C12—C11 | 120.9 (7) |
I1Ai—Cu1A—I1A | 60.3 (5) | C13—C12—H12 | 119.6 |
S1A—Cu1A—I1Ai | 76 (2) | C12—C13—H13 | 120.0 |
S1A—Cu1A—I1A | 103 (2) | C12—C13—C14 | 119.9 (8) |
Cu1Ai—I1A—Cu1A | 119.7 (5) | C14—C13—H13 | 120.0 |
Cu1Ai—I1A—I1Ai | 61.3 (6) | C15—C14—C13 | 120.6 (8) |
I1Ai—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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I1i | 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[µ
4-iodido-µ
3-iodido-[
N-(benzo[
d]thiazol-2-yl)benzamide-
κN]dicopper(I)] (II)
top
Crystal data top
[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) Å3 | Needle, brown |
Z = 2 | 0.57 × 0.09 × 0.06 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0771P)2 + 6.6934P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
I2—Cu2i | 2.6431 (18) | C25—C20 | 1.370 (17) |
I2—Cu2 | 2.6905 (18) | C21—C22 | 1.386 (18) |
I2—Cu2ii | 2.6473 (18) | C21—C20 | 1.392 (17) |
I2—Cu1ii | 2.658 (2) | C22—H22 | 0.9500 |
I1—Cu2 | 2.6216 (17) | C22—C23 | 1.406 (17) |
I1—Cu1ii | 2.704 (2) | C13—H13 | 0.9500 |
I1—Cu1 | 2.647 (2) | C13—C14 | 1.38 (2) |
Cu2—Cu2iii | 2.885 (2) | C13—C12 | 1.403 (19) |
Cu2—Cu2i | 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) | | |
| | | |
Cu2i—I2—Cu2ii | 66.11 (5) | C1—N2—C20 | 111.6 (10) |
Cu2ii—I2—Cu2 | 100.88 (5) | C20—N2—Cu1 | 125.8 (8) |
Cu2i—I2—Cu2 | 65.50 (5) | N1—C1—S1 | 121.9 (8) |
Cu2i—I2—Cu1ii | 106.14 (6) | N2—C1—S1 | 115.7 (9) |
Cu2ii—I2—Cu1ii | 61.97 (6) | N2—C1—N1 | 122.3 (10) |
Cu1ii—I2—Cu2 | 76.87 (6) | C24—C25—H25 | 120.9 |
Cu2—I1—Cu1 | 62.45 (6) | C20—C25—H25 | 120.9 |
Cu2—I1—Cu1ii | 77.24 (6) | C20—C25—C24 | 118.2 (11) |
Cu1—I1—Cu1ii | 100.52 (6) | C22—C21—S1 | 127.4 (10) |
I2iii—Cu2—I2iv | 114.92 (7) | C22—C21—C20 | 121.6 (11) |
I2iii—Cu2—I2 | 113.47 (6) | C20—C21—S1 | 111.0 (9) |
I2iv—Cu2—I2 | 100.88 (5) | C21—C22—H22 | 121.2 |
I2iv—Cu2—Cu2i | 123.16 (8) | C21—C22—C23 | 117.6 (11) |
I2iii—Cu2—Cu2iii | 58.04 (6) | C23—C22—H22 | 121.2 |
I2—Cu2—Cu2i | 56.46 (4) | C14—C13—H13 | 119.2 |
I2iii—Cu2—Cu2i | 57.02 (6) | C14—C13—C12 | 121.6 (14) |
I2iv—Cu2—Cu2iii | 56.88 (4) | C12—C13—H13 | 119.2 |
I2—Cu2—Cu2iii | 123.57 (8) | O1—C10—N1 | 120.0 (12) |
I2—Cu2—Cu1 | 113.83 (7) | O1—C10—C11 | 123.8 (11) |
I2iv—Cu2—Cu1 | 59.21 (5) | N1—C10—C11 | 116.2 (11) |
I2iii—Cu2—Cu1 | 132.51 (8) | C25—C24—H24 | 119.7 |
I1—Cu2—I2 | 103.62 (6) | C25—C24—C23 | 120.7 (12) |
I1—Cu2—I2iii | 105.17 (6) | C23—C24—H24 | 119.7 |
I1—Cu2—I2iv | 118.44 (6) | C13—C14—H14 | 120.6 |
I1—Cu2—Cu2iii | 132.81 (7) | C13—C14—C15 | 118.9 (13) |
I1—Cu2—Cu2i | 117.53 (6) | C15—C14—H14 | 120.6 |
I1—Cu2—Cu1 | 59.23 (6) | C25—C20—N2 | 125.2 (11) |
Cu2iii—Cu2—Cu2i | 90.97 (9) | C25—C20—C21 | 121.6 (11) |
Cu1—Cu2—Cu2i | 169.75 (8) | C21—C20—N2 | 113.2 (10) |
Cu1—Cu2—Cu2iii | 97.92 (5) | C12—C11—C10 | 116.9 (11) |
I2iv—Cu1—I1iv | 102.26 (7) | C12—C11—C16 | 120.2 (12) |
I2iv—Cu1—Cu2 | 58.81 (5) | C16—C11—C10 | 122.9 (12) |
I1—Cu1—I2iv | 117.13 (7) | C13—C12—C11 | 118.4 (13) |
I1—Cu1—I1iv | 100.52 (6) | C13—C12—H12 | 120.8 |
I1iv—Cu1—Cu2 | 112.88 (7) | C11—C12—H12 | 120.8 |
I1—Cu1—Cu2 | 58.32 (5) | C22—C23—C24 | 120.3 (12) |
N2—Cu1—I2iv | 116.8 (3) | C22—C23—H23 | 119.9 |
N2—Cu1—I1iv | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I1iv | 0.88 | 2.80 | 3.654 (10) | 164 |
Symmetry code: (iv) x, y−1, z. |
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