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In the structure of the title compound, [CuCl
2(C
4H
6N
2)
4], the copper(II) cation is surrounded by four 4-methylimidazole ligands within a slightly distorted square plane. The coordination sphere is completed by two contacts to Cl atoms which are elongated due to the Jahn–Teller distortion. The coordination polyhedron around the copper(II) cations can be described as a strongly distorted octahedron. The copper(II) cations are located on centres of inversion, whereas the two crystallographically independent 4-methylimidazole ligands and the chloride anion occupy general positions. There are short N—H
Cl distances to the Cl atoms indicating hydrogen bonding.
Supporting information
CCDC reference: 180754
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.101
- Data-to-parameter ratio = 24.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
WEIGH_01 Alert C Extra text has been found in the
_refine_ls_weighting_scheme field. This should be in the
_refine_ls_weighting_details field.
Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.288
Weighting scheme identified as calc
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: CIFTAB in SHELXL97.
Crystal data top
[CuCl2(C4H6N2)4] | F(000) = 478 |
Mr = 462.87 | Dx = 1.422 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0925 (8) Å | Cell parameters from 130 reflections |
b = 11.8347 (7) Å | θ = 15–19.5° |
c = 11.3012 (11) Å | µ = 1.28 mm−1 |
β = 93.063 (12)° | T = 293 K |
V = 1080.80 (16) Å3 | Block, blue |
Z = 2 | 0.12 × 0.09 × 0.05 mm |
Data collection top
STOE AED-II 4-circle diffractometer | 2550 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 30.0°, θmin = 2.5° |
ω–θ scans | h = 0→11 |
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 1998) | k = −16→10 |
Tmin = 0.782, Tmax = 0.846 | l = −15→15 |
5869 measured reflections | 4 standard reflections every 120 min |
3152 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.101 | Calculated w = 1/[σ2(Fo2) + (0.0583P)2 + 0.2887P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3152 reflections | Δρmax = 0.86 e Å−3 |
129 parameters | Δρmin = −0.54 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0055 (14) |
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 | Occ. (<1) |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.03561 (11) | |
Cl1 | 0.33133 (6) | 0.52563 (4) | 0.73222 (5) | 0.04393 (13) | |
N1 | 0.70903 (18) | 0.45105 (12) | 0.59056 (13) | 0.0345 (3) | |
C1 | 0.8479 (2) | 0.50838 (15) | 0.60344 (17) | 0.0372 (4) | |
H1 | 0.8669 | 0.5775 | 0.5675 | 0.045* | |
N2 | 0.95871 (18) | 0.45399 (14) | 0.67522 (14) | 0.0406 (3) | |
H2 | 1.0572 | 0.4769 | 0.6951 | 0.049* | |
C2 | 0.8878 (2) | 0.35564 (16) | 0.71133 (18) | 0.0421 (4) | |
C3 | 0.7337 (2) | 0.35456 (16) | 0.65753 (17) | 0.0420 (4) | |
H3 | 0.6563 | 0.2972 | 0.6648 | 0.050* | |
C4 | 0.9720 (3) | 0.2752 (2) | 0.7958 (3) | 0.0685 (7) | |
H4A | 1.0780 | 0.3051 | 0.8220 | 0.103* | 0.30 (4) |
H4B | 0.9867 | 0.2040 | 0.7571 | 0.103* | 0.30 (4) |
H4C | 0.9056 | 0.2646 | 0.8628 | 0.103* | 0.30 (4) |
H4D | 0.9022 | 0.2107 | 0.8059 | 0.103* | 0.70 (4) |
H4E | 0.9935 | 0.3118 | 0.8708 | 0.103* | 0.70 (4) |
H4F | 1.0746 | 0.2512 | 0.7651 | 0.103* | 0.70 (4) |
N3 | 0.57309 (18) | 0.66232 (11) | 0.51208 (12) | 0.0340 (3) | |
C11 | 0.5416 (2) | 0.73070 (15) | 0.59886 (16) | 0.0406 (4) | |
H11 | 0.4847 | 0.7104 | 0.6650 | 0.049* | |
N4 | 0.6025 (2) | 0.83434 (13) | 0.57976 (15) | 0.0433 (4) | |
H4 | 0.5953 | 0.8917 | 0.6259 | 0.052* | |
C12 | 0.6777 (2) | 0.83283 (15) | 0.47490 (17) | 0.0403 (4) | |
C13 | 0.6594 (2) | 0.72576 (15) | 0.43381 (16) | 0.0389 (4) | |
H13 | 0.6991 | 0.6991 | 0.3633 | 0.047* | |
C14 | 0.7562 (4) | 0.9356 (2) | 0.4257 (2) | 0.0687 (7) | |
H14A | 0.7307 | 1.0002 | 0.4728 | 0.103* | 0.63 (4) |
H14B | 0.7144 | 0.9473 | 0.3455 | 0.103* | 0.63 (4) |
H14C | 0.8740 | 0.9255 | 0.4271 | 0.103* | 0.63 (4) |
H14D | 0.8153 | 0.9151 | 0.3575 | 0.103* | 0.37 (4) |
H14E | 0.8317 | 0.9680 | 0.4848 | 0.103* | 0.37 (4) |
H14F | 0.6721 | 0.9899 | 0.4032 | 0.103* | 0.37 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.03381 (17) | 0.02345 (15) | 0.04785 (19) | −0.00566 (10) | −0.01376 (12) | 0.00174 (10) |
Cl1 | 0.0368 (2) | 0.0371 (2) | 0.0572 (3) | −0.00423 (16) | −0.00485 (18) | 0.01140 (18) |
N1 | 0.0323 (7) | 0.0307 (7) | 0.0397 (7) | −0.0041 (5) | −0.0065 (5) | 0.0020 (5) |
C1 | 0.0315 (8) | 0.0355 (8) | 0.0440 (9) | −0.0045 (6) | −0.0033 (7) | 0.0024 (6) |
N2 | 0.0286 (7) | 0.0390 (8) | 0.0533 (9) | −0.0030 (6) | −0.0063 (6) | 0.0014 (7) |
C2 | 0.0349 (8) | 0.0363 (9) | 0.0538 (10) | 0.0001 (7) | −0.0086 (7) | 0.0058 (7) |
C3 | 0.0348 (8) | 0.0347 (8) | 0.0553 (10) | −0.0070 (6) | −0.0085 (7) | 0.0095 (7) |
C4 | 0.0507 (12) | 0.0580 (14) | 0.0937 (17) | −0.0021 (10) | −0.0240 (12) | 0.0285 (13) |
N3 | 0.0347 (7) | 0.0264 (6) | 0.0399 (7) | −0.0053 (5) | −0.0064 (5) | 0.0002 (5) |
C11 | 0.0449 (9) | 0.0333 (8) | 0.0437 (9) | −0.0079 (7) | 0.0038 (7) | −0.0018 (7) |
N4 | 0.0511 (9) | 0.0280 (7) | 0.0505 (8) | −0.0069 (6) | 0.0008 (7) | −0.0073 (6) |
C12 | 0.0420 (9) | 0.0312 (8) | 0.0470 (9) | −0.0077 (7) | −0.0046 (7) | 0.0056 (7) |
C13 | 0.0433 (9) | 0.0345 (8) | 0.0386 (8) | −0.0059 (7) | −0.0007 (7) | −0.0001 (6) |
C14 | 0.0860 (18) | 0.0457 (12) | 0.0745 (16) | −0.0255 (12) | 0.0054 (14) | 0.0124 (11) |
Geometric parameters (Å, º) top
Cu1—N3 | 2.0124 (13) | C4—H4E | 0.9600 |
Cu1—N3i | 2.0124 (13) | C4—H4F | 0.9600 |
Cu1—N1i | 2.0148 (14) | N3—C11 | 1.307 (2) |
Cu1—N1 | 2.0148 (14) | N3—C13 | 1.378 (2) |
N1—C1 | 1.314 (2) | C11—N4 | 1.344 (2) |
N1—C3 | 1.379 (2) | C11—H11 | 0.9300 |
C1—N2 | 1.341 (2) | N4—C12 | 1.361 (3) |
C1—H1 | 0.9300 | N4—H4 | 0.8600 |
N2—C2 | 1.370 (2) | C12—C13 | 1.355 (2) |
N2—H2 | 0.8600 | C12—C14 | 1.494 (3) |
C2—C3 | 1.358 (2) | C13—H13 | 0.9300 |
C2—C4 | 1.487 (3) | C14—H14A | 0.9600 |
C3—H3 | 0.9300 | C14—H14B | 0.9600 |
C4—H4A | 0.9600 | C14—H14C | 0.9600 |
C4—H4B | 0.9600 | C14—H14D | 0.9600 |
C4—H4C | 0.9600 | C14—H14E | 0.9600 |
C4—H4D | 0.9600 | C14—H14F | 0.9600 |
| | | |
N3—Cu1—N3i | 180.0 | H4C—C4—H4F | 141.1 |
N3—Cu1—N1i | 89.76 (6) | H4D—C4—H4F | 109.5 |
N3i—Cu1—N1i | 90.24 (6) | H4E—C4—H4F | 109.5 |
N3—Cu1—N1 | 90.24 (6) | C11—N3—C13 | 105.66 (14) |
N3i—Cu1—N1 | 89.76 (6) | C11—N3—Cu1 | 125.01 (12) |
N1i—Cu1—N1 | 180.0 | C13—N3—Cu1 | 129.31 (12) |
C1—N1—C3 | 105.60 (14) | N3—C11—N4 | 110.91 (16) |
C1—N1—Cu1 | 126.71 (12) | N3—C11—H11 | 124.5 |
C3—N1—Cu1 | 127.59 (11) | N4—C11—H11 | 124.5 |
N1—C1—N2 | 111.06 (15) | C11—N4—C12 | 108.23 (15) |
N1—C1—H1 | 124.5 | C11—N4—H4 | 125.9 |
N2—C1—H1 | 124.5 | C12—N4—H4 | 125.9 |
C1—N2—C2 | 108.12 (15) | C13—C12—N4 | 105.37 (16) |
C1—N2—H2 | 125.9 | C13—C12—C14 | 132.5 (2) |
C2—N2—H2 | 125.9 | N4—C12—C14 | 122.17 (19) |
C3—C2—N2 | 105.30 (15) | C12—C13—N3 | 109.84 (16) |
C3—C2—C4 | 131.27 (19) | C12—C13—H13 | 125.1 |
N2—C2—C4 | 123.39 (17) | N3—C13—H13 | 125.1 |
C2—C3—N1 | 109.91 (16) | C12—C14—H14A | 109.5 |
C2—C3—H3 | 125.0 | C12—C14—H14B | 109.5 |
N1—C3—H3 | 125.0 | H14A—C14—H14B | 109.5 |
C2—C4—H4A | 109.5 | C12—C14—H14C | 109.5 |
C2—C4—H4B | 109.5 | H14A—C14—H14C | 109.5 |
H4A—C4—H4B | 109.5 | H14B—C14—H14C | 109.5 |
C2—C4—H4C | 109.5 | C12—C14—H14D | 109.5 |
H4A—C4—H4C | 109.5 | H14A—C14—H14D | 141.1 |
H4B—C4—H4C | 109.5 | H14B—C14—H14D | 56.3 |
C2—C4—H4D | 109.5 | H14C—C14—H14D | 56.3 |
H4A—C4—H4D | 141.1 | C12—C14—H14E | 109.5 |
H4B—C4—H4D | 56.3 | H14A—C14—H14E | 56.3 |
H4C—C4—H4D | 56.3 | H14B—C14—H14E | 141.1 |
C2—C4—H4E | 109.5 | H14C—C14—H14E | 56.3 |
H4A—C4—H4E | 56.3 | H14D—C14—H14E | 109.5 |
H4B—C4—H4E | 141.1 | C12—C14—H14F | 109.5 |
H4C—C4—H4E | 56.3 | H14A—C14—H14F | 56.3 |
H4D—C4—H4E | 109.5 | H14B—C14—H14F | 56.3 |
C2—C4—H4F | 109.5 | H14C—C14—H14F | 141.1 |
H4A—C4—H4F | 56.3 | H14D—C14—H14F | 109.5 |
H4B—C4—H4F | 56.3 | H14E—C14—H14F | 109.5 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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