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In the structure of the title compound, [CuCl2(C4H6N2)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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000314/bt6099sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000314/bt6099Isup2.hkl
Contains datablock I

CCDC reference: 180754

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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


Yellow Alert 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

Computing details top

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.

(I) top
Crystal data top
[CuCl2(C4H6N2)4]F(000) = 478
Mr = 462.87Dx = 1.422 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.0925 (8) ÅCell parameters from 130 reflections
b = 11.8347 (7) Åθ = 15–19.5°
c = 11.3012 (11) ŵ = 1.28 mm1
β = 93.063 (12)°T = 293 K
V = 1080.80 (16) Å3Block, blue
Z = 20.12 × 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 tubeRint = 0.027
Graphite monochromatorθmax = 30.0°, θmin = 2.5°
ωθ scansh = 011
Absorption correction: numerical
(X-SHAPE; Stoe & Cie, 1998)
k = 1610
Tmin = 0.782, Tmax = 0.846l = 1515
5869 measured reflections4 standard reflections every 120 min
3152 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101Calculated w = 1/[σ2(Fo2) + (0.0583P)2 + 0.2887P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3152 reflectionsΔρmax = 0.86 e Å3
129 parametersΔρmin = 0.54 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/UeqOcc. (<1)
Cu10.50000.50000.50000.03561 (11)
Cl10.33133 (6)0.52563 (4)0.73222 (5)0.04393 (13)
N10.70903 (18)0.45105 (12)0.59056 (13)0.0345 (3)
C10.8479 (2)0.50838 (15)0.60344 (17)0.0372 (4)
H10.86690.57750.56750.045*
N20.95871 (18)0.45399 (14)0.67522 (14)0.0406 (3)
H21.05720.47690.69510.049*
C20.8878 (2)0.35564 (16)0.71133 (18)0.0421 (4)
C30.7337 (2)0.35456 (16)0.65753 (17)0.0420 (4)
H30.65630.29720.66480.050*
C40.9720 (3)0.2752 (2)0.7958 (3)0.0685 (7)
H4A1.07800.30510.82200.103*0.30 (4)
H4B0.98670.20400.75710.103*0.30 (4)
H4C0.90560.26460.86280.103*0.30 (4)
H4D0.90220.21070.80590.103*0.70 (4)
H4E0.99350.31180.87080.103*0.70 (4)
H4F1.07460.25120.76510.103*0.70 (4)
N30.57309 (18)0.66232 (11)0.51208 (12)0.0340 (3)
C110.5416 (2)0.73070 (15)0.59886 (16)0.0406 (4)
H110.48470.71040.66500.049*
N40.6025 (2)0.83434 (13)0.57976 (15)0.0433 (4)
H40.59530.89170.62590.052*
C120.6777 (2)0.83283 (15)0.47490 (17)0.0403 (4)
C130.6594 (2)0.72576 (15)0.43381 (16)0.0389 (4)
H130.69910.69910.36330.047*
C140.7562 (4)0.9356 (2)0.4257 (2)0.0687 (7)
H14A0.73071.00020.47280.103*0.63 (4)
H14B0.71440.94730.34550.103*0.63 (4)
H14C0.87400.92550.42710.103*0.63 (4)
H14D0.81530.91510.35750.103*0.37 (4)
H14E0.83170.96800.48480.103*0.37 (4)
H14F0.67210.98990.40320.103*0.37 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03381 (17)0.02345 (15)0.04785 (19)0.00566 (10)0.01376 (12)0.00174 (10)
Cl10.0368 (2)0.0371 (2)0.0572 (3)0.00423 (16)0.00485 (18)0.01140 (18)
N10.0323 (7)0.0307 (7)0.0397 (7)0.0041 (5)0.0065 (5)0.0020 (5)
C10.0315 (8)0.0355 (8)0.0440 (9)0.0045 (6)0.0033 (7)0.0024 (6)
N20.0286 (7)0.0390 (8)0.0533 (9)0.0030 (6)0.0063 (6)0.0014 (7)
C20.0349 (8)0.0363 (9)0.0538 (10)0.0001 (7)0.0086 (7)0.0058 (7)
C30.0348 (8)0.0347 (8)0.0553 (10)0.0070 (6)0.0085 (7)0.0095 (7)
C40.0507 (12)0.0580 (14)0.0937 (17)0.0021 (10)0.0240 (12)0.0285 (13)
N30.0347 (7)0.0264 (6)0.0399 (7)0.0053 (5)0.0064 (5)0.0002 (5)
C110.0449 (9)0.0333 (8)0.0437 (9)0.0079 (7)0.0038 (7)0.0018 (7)
N40.0511 (9)0.0280 (7)0.0505 (8)0.0069 (6)0.0008 (7)0.0073 (6)
C120.0420 (9)0.0312 (8)0.0470 (9)0.0077 (7)0.0046 (7)0.0056 (7)
C130.0433 (9)0.0345 (8)0.0386 (8)0.0059 (7)0.0007 (7)0.0001 (6)
C140.0860 (18)0.0457 (12)0.0745 (16)0.0255 (12)0.0054 (14)0.0124 (11)
Geometric parameters (Å, º) top
Cu1—N32.0124 (13)C4—H4E0.9600
Cu1—N3i2.0124 (13)C4—H4F0.9600
Cu1—N1i2.0148 (14)N3—C111.307 (2)
Cu1—N12.0148 (14)N3—C131.378 (2)
N1—C11.314 (2)C11—N41.344 (2)
N1—C31.379 (2)C11—H110.9300
C1—N21.341 (2)N4—C121.361 (3)
C1—H10.9300N4—H40.8600
N2—C21.370 (2)C12—C131.355 (2)
N2—H20.8600C12—C141.494 (3)
C2—C31.358 (2)C13—H130.9300
C2—C41.487 (3)C14—H14A0.9600
C3—H30.9300C14—H14B0.9600
C4—H4A0.9600C14—H14C0.9600
C4—H4B0.9600C14—H14D0.9600
C4—H4C0.9600C14—H14E0.9600
C4—H4D0.9600C14—H14F0.9600
N3—Cu1—N3i180.0H4C—C4—H4F141.1
N3—Cu1—N1i89.76 (6)H4D—C4—H4F109.5
N3i—Cu1—N1i90.24 (6)H4E—C4—H4F109.5
N3—Cu1—N190.24 (6)C11—N3—C13105.66 (14)
N3i—Cu1—N189.76 (6)C11—N3—Cu1125.01 (12)
N1i—Cu1—N1180.0C13—N3—Cu1129.31 (12)
C1—N1—C3105.60 (14)N3—C11—N4110.91 (16)
C1—N1—Cu1126.71 (12)N3—C11—H11124.5
C3—N1—Cu1127.59 (11)N4—C11—H11124.5
N1—C1—N2111.06 (15)C11—N4—C12108.23 (15)
N1—C1—H1124.5C11—N4—H4125.9
N2—C1—H1124.5C12—N4—H4125.9
C1—N2—C2108.12 (15)C13—C12—N4105.37 (16)
C1—N2—H2125.9C13—C12—C14132.5 (2)
C2—N2—H2125.9N4—C12—C14122.17 (19)
C3—C2—N2105.30 (15)C12—C13—N3109.84 (16)
C3—C2—C4131.27 (19)C12—C13—H13125.1
N2—C2—C4123.39 (17)N3—C13—H13125.1
C2—C3—N1109.91 (16)C12—C14—H14A109.5
C2—C3—H3125.0C12—C14—H14B109.5
N1—C3—H3125.0H14A—C14—H14B109.5
C2—C4—H4A109.5C12—C14—H14C109.5
C2—C4—H4B109.5H14A—C14—H14C109.5
H4A—C4—H4B109.5H14B—C14—H14C109.5
C2—C4—H4C109.5C12—C14—H14D109.5
H4A—C4—H4C109.5H14A—C14—H14D141.1
H4B—C4—H4C109.5H14B—C14—H14D56.3
C2—C4—H4D109.5H14C—C14—H14D56.3
H4A—C4—H4D141.1C12—C14—H14E109.5
H4B—C4—H4D56.3H14A—C14—H14E56.3
H4C—C4—H4D56.3H14B—C14—H14E141.1
C2—C4—H4E109.5H14C—C14—H14E56.3
H4A—C4—H4E56.3H14D—C14—H14E109.5
H4B—C4—H4E141.1C12—C14—H14F109.5
H4C—C4—H4E56.3H14A—C14—H14F56.3
H4D—C4—H4E109.5H14B—C14—H14F56.3
C2—C4—H4F109.5H14C—C14—H14F141.1
H4A—C4—H4F56.3H14D—C14—H14F109.5
H4B—C4—H4F56.3H14E—C14—H14F109.5
Symmetry code: (i) x+1, y+1, z+1.
 

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