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By using alternating-current electrochemical synthesis, crystals of the copper(I) ionic compound composed of [Cu(C8H8N2)2]+ and [CuCl2]− ions have been obtained and structurally investigated. Both crystallographically independent Cu atoms lie on centres of inversion and exhibit the less-common coordination number 2. A linear arrangement of the metal atoms includes two N atoms of the different organic moieties in the [Cu(2-methylbenzimidazole)2]+ cation and two Cl atoms in the case of the inorganic anion.
Supporting information
CCDC reference: 236023
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.124
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD4- Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMIND (Bergerhoff, 1996); software used to prepare material for publication: enCIFer (CCDC, 2002).
Crystal data top
[Cu(C8H8N2)2][CuCl2] | Z = 1 |
Mr = 462.31 | F(000) = 232 |
Triclinic, P1 | Dx = 1.690 Mg m−3 Dm = 1.7 Mg m−3 Dm measured by flotation in chloroform–bromoform |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 7.251 (1) Å | Cell parameters from 25 reflections |
b = 7.4873 (10) Å | θ = 65–73° |
c = 9.7058 (13) Å | µ = 5.63 mm−1 |
α = 112.628 (10)° | T = 295 K |
β = 98.786 (11)° | Block, colourless |
γ = 103.832 (11)° | 0.40 × 0.20 × 0.20 mm |
V = 454.32 (11) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 1676 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Graphite monochromator | θmax = 74.0°, θmin = 5.1° |
θ/2ω scans | h = −9→0 |
Absorption correction: numerical (de Meulanear & Tompa, 1965) | k = −9→9 |
Tmin = 0.212, Tmax = 0.399 | l = −11→12 |
1986 measured reflections | 3 standard reflections every 60 min |
1835 independent reflections | intensity decay: 3% |
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) = 0.125 | Only H-atom displacement parameters refined |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1751P] where P = (Fo2 + 2Fc2)/3 |
1835 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
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 | Uiso*/Ueq | |
Cu1 | 0.0000 | 0.5000 | 0.5000 | 0.0496 (2) | |
Cu2 | 0.0000 | 1.0000 | 0.0000 | 0.0655 (2) | |
Cl1 | 0.19627 (14) | 1.23371 (13) | 0.20890 (10) | 0.0753 (3) | |
N1 | 0.1253 (3) | 0.7437 (3) | 0.4913 (2) | 0.0433 (4) | |
C2 | 0.1003 (4) | 0.7854 (4) | 0.3706 (3) | 0.0428 (5) | |
N3 | 0.2082 (3) | 0.9796 (3) | 0.4082 (2) | 0.0449 (5) | |
H3 | 0.2024 | 1.0414 | 0.3436 | 0.064 (9)* | |
C4 | 0.3110 (4) | 1.0710 (4) | 0.5622 (3) | 0.0428 (5) | |
C5 | 0.4421 (4) | 1.2658 (4) | 0.6577 (4) | 0.0518 (6) | |
H5 | 0.4701 | 1.3767 | 0.6312 | 0.056 (9)* | |
C6 | 0.5184 (4) | 1.3077 (5) | 0.8095 (4) | 0.0584 (7) | |
H6 | 0.6048 | 1.4442 | 0.8828 | 0.076 (11)* | |
C7 | 0.4662 (5) | 1.1588 (5) | 0.8637 (4) | 0.0622 (7) | |
H7 | 0.5226 | 1.2119 | 0.9809 | 0.070 (10)* | |
C8 | 0.3363 (5) | 0.9661 (5) | 0.7684 (3) | 0.0556 (6) | |
H8 | 0.3075 | 0.8392 | 0.8006 | 0.112 (17)* | |
C9 | 0.2578 (3) | 0.9216 (4) | 0.6142 (3) | 0.0421 (5) | |
C10 | −0.0267 (5) | 0.6406 (5) | 0.2116 (3) | 0.0562 (7) | |
H10A | −0.0189 | 0.7080 | 0.1451 | 0.138 (13)* | |
H10B | −0.1609 | 0.5957 | 0.2147 | 0.138 (13)* | |
H10C | 0.0178 | 0.5245 | 0.1721 | 0.138 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0509 (3) | 0.0363 (3) | 0.0598 (4) | 0.0041 (2) | 0.0099 (2) | 0.0273 (3) |
Cu2 | 0.0808 (5) | 0.0524 (4) | 0.0686 (4) | 0.0163 (3) | 0.0163 (3) | 0.0366 (3) |
Cl1 | 0.0943 (6) | 0.0544 (4) | 0.0730 (5) | 0.0051 (4) | 0.0105 (4) | 0.0396 (4) |
N1 | 0.0470 (11) | 0.0349 (10) | 0.0474 (11) | 0.0085 (8) | 0.0125 (8) | 0.0206 (9) |
C2 | 0.0460 (12) | 0.0371 (11) | 0.0460 (12) | 0.0127 (10) | 0.0136 (10) | 0.0190 (10) |
N3 | 0.0551 (11) | 0.0386 (10) | 0.0468 (11) | 0.0143 (9) | 0.0157 (9) | 0.0246 (9) |
C4 | 0.0446 (12) | 0.0386 (12) | 0.0484 (13) | 0.0124 (10) | 0.0175 (10) | 0.0214 (10) |
C5 | 0.0508 (14) | 0.0364 (12) | 0.0652 (17) | 0.0078 (10) | 0.0212 (12) | 0.0213 (12) |
C6 | 0.0499 (14) | 0.0460 (14) | 0.0599 (16) | 0.0054 (11) | 0.0116 (12) | 0.0111 (13) |
C7 | 0.0583 (16) | 0.0665 (19) | 0.0491 (15) | 0.0125 (14) | 0.0056 (12) | 0.0207 (14) |
C8 | 0.0614 (16) | 0.0548 (16) | 0.0511 (14) | 0.0115 (12) | 0.0115 (12) | 0.0297 (13) |
C9 | 0.0433 (12) | 0.0361 (11) | 0.0466 (12) | 0.0087 (9) | 0.0130 (9) | 0.0201 (10) |
C10 | 0.0628 (16) | 0.0497 (15) | 0.0462 (14) | 0.0154 (12) | 0.0065 (12) | 0.0158 (12) |
Geometric parameters (Å, º) top
Cu1—N1i | 1.874 (2) | C5—C6 | 1.373 (4) |
Cu1—N1 | 1.874 (2) | C5—H5 | 0.9467 |
Cu2—Cl1 | 2.0967 (10) | C6—C7 | 1.405 (5) |
Cu2—Cl1ii | 2.0967 (10) | C6—H6 | 0.9702 |
N1—C2 | 1.321 (3) | C7—C8 | 1.372 (5) |
N1—C9 | 1.391 (3) | C7—H7 | 1.0251 |
C2—N3 | 1.349 (3) | C8—C9 | 1.393 (4) |
C2—C10 | 1.486 (4) | C8—H8 | 1.0947 |
N3—C4 | 1.373 (3) | C10—H10A | 0.9600 |
N3—H3 | 0.9140 | C10—H10B | 0.9600 |
C4—C5 | 1.385 (4) | C10—H10C | 0.9600 |
C4—C9 | 1.393 (3) | | |
| | | |
N1i—Cu1—N1 | 180.0 | C5—C6—H6 | 120.1 |
Cl1—Cu2—Cl1ii | 180.0 | C7—C6—H6 | 118.6 |
C2—N1—C9 | 106.0 (2) | C8—C7—C6 | 121.8 (3) |
C2—N1—Cu1 | 127.52 (17) | C8—C7—H7 | 124.0 |
C9—N1—Cu1 | 126.39 (17) | C6—C7—H7 | 114.0 |
N1—C2—N3 | 111.4 (2) | C7—C8—C9 | 117.6 (3) |
N1—C2—C10 | 125.8 (2) | C7—C8—H8 | 124.2 |
N3—C2—C10 | 122.8 (2) | C9—C8—H8 | 117.6 |
C2—N3—C4 | 108.4 (2) | N1—C9—C4 | 108.9 (2) |
C2—N3—H3 | 124.7 | N1—C9—C8 | 131.1 (2) |
C4—N3—H3 | 126.6 | C4—C9—C8 | 120.0 (2) |
N3—C4—C5 | 131.9 (2) | C2—C10—H10A | 109.5 |
N3—C4—C9 | 105.3 (2) | C2—C10—H10B | 109.5 |
C5—C4—C9 | 122.8 (2) | H10A—C10—H10B | 109.5 |
C6—C5—C4 | 116.7 (3) | C2—C10—H10C | 109.5 |
C6—C5—H5 | 117.2 | H10A—C10—H10C | 109.5 |
C4—C5—H5 | 125.6 | H10B—C10—H10C | 109.5 |
C5—C6—C7 | 121.2 (3) | | |
| | | |
C9—N1—C2—N3 | −0.2 (3) | C6—C7—C8—C9 | 0.5 (5) |
Cu1—N1—C2—N3 | 177.16 (16) | C2—N1—C9—C4 | 0.0 (3) |
C9—N1—C2—C10 | 179.0 (2) | Cu1—N1—C9—C4 | −177.40 (17) |
Cu1—N1—C2—C10 | −3.6 (4) | C2—N1—C9—C8 | 179.6 (3) |
N1—C2—N3—C4 | 0.3 (3) | Cu1—N1—C9—C8 | 2.3 (4) |
C10—C2—N3—C4 | −178.9 (2) | N3—C4—C9—N1 | 0.2 (3) |
C2—N3—C4—C5 | 179.7 (3) | C5—C4—C9—N1 | −179.8 (2) |
C2—N3—C4—C9 | −0.3 (3) | N3—C4—C9—C8 | −179.5 (2) |
N3—C4—C5—C6 | 179.5 (3) | C5—C4—C9—C8 | 0.5 (4) |
C9—C4—C5—C6 | −0.4 (4) | C7—C8—C9—N1 | 179.9 (3) |
C4—C5—C6—C7 | 0.4 (4) | C7—C8—C9—C4 | −0.5 (4) |
C5—C6—C7—C8 | −0.5 (5) | | |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···Cl1 | 0.91 | 2.29 | 3.199 (2) | 173 |
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