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In the title compound, catena-poly[diselanylbis(1,3-dimethyl-1H-imidazol-3-ium) [μ3-chlorido-tetra-μ2-chlorido-tricuprate(I)]], {(C10H16N4Se2)[Cu3Cl5]}n, the diselenide dication is stabilized by catena-[Cu3Cl5]2− anions which associate through strong Cu—Cl bonds [average length = 2.3525 (13) Å] to form polymeric chains. The polymeric [Cu3Cl5]2− anion contains crystallographically imposed twofold rotation symmetry, with distorted trigonal-planar and tetrahedral geometries around the two symmetry-independent Cu atoms. Likewise, the Se—Se bond of the cation is centered on a twofold rotation axis.
Supporting information
CCDC reference: 833411
Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXTL (Version 6.10; Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Version 6.10; Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Version 6.10; Sheldrick, 2008).
catena-poly[diselanylbis(1,3-dimethyl-1
H-imidazol-3-ium)
[µ
3-chlorido-tetra-µ
2-chlorido-tricuprate(I)]]
top
Crystal data top
(C10H16N4Se2)[Cu3Cl5] | F(000) = 1376 |
Mr = 718.06 | Dx = 2.383 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8327 reflections |
a = 12.238 (2) Å | θ = 3.0–26.3° |
b = 12.217 (2) Å | µ = 7.47 mm−1 |
c = 14.123 (3) Å | T = 168 K |
β = 108.61 (3)° | Prism, red |
V = 2001.2 (7) Å3 | 0.32 × 0.25 × 0.23 mm |
Z = 4 | |
Data collection top
Rigaku AFC-8S diffractometer | 2022 independent reflections |
Radiation source: fine-focus sealed tube | 1698 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 14.6306 pixels mm-1 | θmax = 26.3°, θmin = 3.0° |
dtprofit.ref scans | h = −10→15 |
Absorption correction: multi-scan [REQAB (Jacobson, 1998) and CrystalClear (Rigaku/MSC, 2006)] | k = −15→15 |
Tmin = 0.199, Tmax = 0.279 | l = −17→17 |
8327 measured reflections | |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0525P)2 + 17.9833P] where P = (Fo2 + 2Fc2)/3 |
2022 reflections | (Δ/σ)max < 0.001 |
112 parameters | Δρmax = 1.22 e Å−3 |
0 restraints | Δρmin = −1.12 e Å−3 |
Special details top
Experimental. 1H and 13C{1H} NMR spectra were obtained on a
Bruker AVANCE 500 NMR spectrometer. 1H and 13C{1H} NMR chemical shifts
are reported in δ relative to trimethylsilane (TMS; δ 0). IR spectra
were obtained using Nujol mulls on KBr salt plates using a Magna 550 IR
spectrometer. Abbreviations used in the description of vibrational data are as
follows: v, very strong; s, strong; m, medium; w, weak; b, broad.
Electrospray ionization mass spectrometry (ESI–MS) was conducted using a QSTAR
XL Hybrid MS/MS System from Applied Biosystems via direct injection of
sample (0.05 ml/min flow rate) into a Turbo Ionspray ionization source.
Samples were run under positive mode with an ionspray voltage of 5500, and in
TOF scan mode. The melting point was determined using a Barnstead
Electrothermal 9100 apparatus in glass capillary tube. |
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 | Uiso*/Ueq | |
Se1 | 0.09498 (4) | 0.50479 (4) | 0.30948 (4) | 0.02044 (17) | |
C1 | 0.1423 (4) | 0.3795 (4) | 0.2552 (4) | 0.0229 (10) | |
C2 | 0.1735 (7) | 0.4644 (6) | 0.1053 (5) | 0.0429 (16) | |
H2A | 0.1389 | 0.5276 | 0.1243 | 0.064* | |
H2B | 0.1309 | 0.4445 | 0.0378 | 0.064* | |
H2C | 0.2517 | 0.4808 | 0.1098 | 0.064* | |
C3 | 0.1967 (6) | 0.2673 (6) | 0.1559 (5) | 0.0397 (15) | |
H3A | 0.2193 | 0.2413 | 0.1031 | 0.048* | |
C4 | 0.1825 (6) | 0.2072 (6) | 0.2300 (5) | 0.0393 (15) | |
H4A | 0.1929 | 0.1319 | 0.2379 | 0.047* | |
C5 | 0.1259 (7) | 0.2423 (5) | 0.3826 (5) | 0.0412 (16) | |
H5A | 0.1130 | 0.3058 | 0.4175 | 0.062* | |
H5B | 0.1905 | 0.2020 | 0.4248 | 0.062* | |
H5C | 0.0585 | 0.1967 | 0.3649 | 0.062* | |
N1 | 0.1720 (4) | 0.3746 (4) | 0.1711 (4) | 0.0294 (10) | |
N2 | 0.1500 (4) | 0.2762 (4) | 0.2921 (4) | 0.0289 (10) | |
Cu1 | 1.0000 | 0.21630 (12) | 0.7500 | 0.0473 (3) | |
Cu2 | 0.99660 (7) | 0.07647 (7) | 0.58139 (6) | 0.0400 (2) | |
Cl1 | 1.00610 (14) | 0.26957 (10) | 0.90297 (10) | 0.0331 (3) | |
Cl3 | 0.84410 (11) | −0.00548 (11) | 0.45362 (10) | 0.0266 (3) | |
Cl2 | 1.0000 | 0.01325 (17) | 0.7500 | 0.0364 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Se1 | 0.0223 (3) | 0.0197 (3) | 0.0192 (3) | −0.00136 (18) | 0.0066 (2) | −0.00184 (18) |
C1 | 0.016 (2) | 0.027 (3) | 0.024 (2) | −0.0002 (19) | 0.0042 (19) | −0.005 (2) |
C2 | 0.052 (4) | 0.049 (4) | 0.037 (3) | −0.016 (3) | 0.027 (3) | −0.008 (3) |
C3 | 0.035 (3) | 0.044 (4) | 0.040 (3) | 0.005 (3) | 0.013 (3) | −0.021 (3) |
C4 | 0.039 (4) | 0.032 (3) | 0.042 (3) | 0.015 (3) | 0.005 (3) | −0.004 (3) |
C5 | 0.057 (4) | 0.031 (3) | 0.026 (3) | 0.000 (3) | 0.001 (3) | 0.005 (2) |
N1 | 0.023 (2) | 0.038 (3) | 0.028 (2) | −0.003 (2) | 0.0095 (19) | −0.011 (2) |
N2 | 0.031 (2) | 0.025 (2) | 0.027 (2) | 0.0067 (19) | 0.003 (2) | −0.0046 (18) |
Cu1 | 0.0458 (7) | 0.0626 (8) | 0.0308 (6) | 0.000 | 0.0086 (5) | 0.000 |
Cu2 | 0.0358 (5) | 0.0387 (5) | 0.0461 (5) | 0.0001 (3) | 0.0139 (4) | −0.0141 (3) |
Cl1 | 0.0557 (9) | 0.0172 (6) | 0.0230 (6) | −0.0068 (6) | 0.0077 (6) | 0.0020 (5) |
Cl3 | 0.0212 (6) | 0.0356 (7) | 0.0226 (6) | 0.0000 (5) | 0.0063 (5) | −0.0014 (5) |
Cl2 | 0.0586 (14) | 0.0302 (10) | 0.0234 (9) | 0.000 | 0.0174 (9) | 0.000 |
Geometric parameters (Å, º) top
Se1—C1 | 1.884 (5) | C5—H5B | 0.9600 |
Se1—Se1i | 2.3946 (13) | C5—H5C | 0.9600 |
C1—N1 | 1.349 (7) | Cu1—Cl1ii | 2.2346 (15) |
C1—N2 | 1.357 (7) | Cu1—Cl1 | 2.2346 (15) |
C2—N1 | 1.442 (9) | Cu1—Cl2 | 2.481 (3) |
C2—H2A | 0.9600 | Cu1—Cu2 | 2.9201 (12) |
C2—H2B | 0.9600 | Cu1—Cu2ii | 2.9201 (12) |
C2—H2C | 0.9600 | Cu2—Cl3iii | 2.3264 (16) |
C3—C4 | 1.335 (11) | Cu2—Cl3 | 2.3648 (17) |
C3—N1 | 1.377 (8) | Cu2—Cl1ii | 2.3707 (16) |
C3—H3A | 0.9300 | Cu2—Cl2 | 2.4910 (12) |
C4—N2 | 1.364 (8) | Cu2—Cu2iii | 2.9843 (16) |
C4—H4A | 0.9300 | Cl1—Cu2ii | 2.3708 (16) |
C5—N2 | 1.460 (8) | Cl3—Cu2iii | 2.3264 (16) |
C5—H5A | 0.9600 | Cl2—Cu2ii | 2.4910 (12) |
| | | |
C1—Se1—Se1i | 94.01 (15) | Cl1ii—Cu1—Cl2 | 106.94 (5) |
N1—C1—N2 | 106.9 (5) | Cl1—Cu1—Cl2 | 106.94 (5) |
N1—C1—Se1 | 126.7 (4) | Cl1ii—Cu1—Cu2 | 52.75 (4) |
N2—C1—Se1 | 126.3 (4) | Cl1—Cu1—Cu2 | 161.11 (7) |
N1—C2—H2A | 109.5 | Cl2—Cu1—Cu2 | 54.20 (3) |
N1—C2—H2B | 109.5 | Cl1ii—Cu1—Cu2ii | 161.11 (7) |
H2A—C2—H2B | 109.5 | Cl1—Cu1—Cu2ii | 52.75 (4) |
N1—C2—H2C | 109.5 | Cl2—Cu1—Cu2ii | 54.20 (3) |
H2A—C2—H2C | 109.5 | Cu2—Cu1—Cu2ii | 108.39 (6) |
H2B—C2—H2C | 109.5 | Cl3iii—Cu2—Cl3 | 101.00 (5) |
C4—C3—N1 | 108.1 (5) | Cl3iii—Cu2—Cl1ii | 115.36 (6) |
C4—C3—H3A | 125.9 | Cl3—Cu2—Cl1ii | 117.47 (6) |
N1—C3—H3A | 125.9 | Cl3iii—Cu2—Cl2 | 109.15 (6) |
C3—C4—N2 | 107.5 (6) | Cl3—Cu2—Cl2 | 111.50 (6) |
C3—C4—H4A | 126.2 | Cl1ii—Cu2—Cl2 | 102.47 (6) |
N2—C4—H4A | 126.2 | Cl3iii—Cu2—Cu1 | 126.62 (5) |
N2—C5—H5A | 109.5 | Cl3—Cu2—Cu1 | 132.25 (5) |
N2—C5—H5B | 109.5 | Cl1ii—Cu2—Cu1 | 48.61 (4) |
H5A—C5—H5B | 109.5 | Cl2—Cu2—Cu1 | 53.87 (5) |
N2—C5—H5C | 109.5 | Cl3iii—Cu2—Cu2iii | 51.07 (4) |
H5A—C5—H5C | 109.5 | Cl3—Cu2—Cu2iii | 49.93 (4) |
H5B—C5—H5C | 109.5 | Cl1ii—Cu2—Cu2iii | 134.38 (6) |
C1—N1—C3 | 108.3 (5) | Cl2—Cu2—Cu2iii | 123.11 (7) |
C1—N1—C2 | 126.6 (5) | Cu1—Cu2—Cu2iii | 176.25 (6) |
C3—N1—C2 | 125.0 (5) | Cu1—Cl1—Cu2ii | 78.64 (6) |
C1—N2—C4 | 109.1 (5) | Cu2iii—Cl3—Cu2 | 79.00 (5) |
C1—N2—C5 | 126.2 (5) | Cu1—Cl2—Cu2ii | 71.94 (5) |
C4—N2—C5 | 124.7 (5) | Cu1—Cl2—Cu2 | 71.94 (5) |
Cl1ii—Cu1—Cl1 | 146.13 (10) | Cu2ii—Cl2—Cu2 | 143.88 (10) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+2, y, −z+3/2; (iii) −x+2, −y, −z+1. |
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