metal-organic compounds
Bromidotetrakis(2-ethyl-1H-imidazole-κN3)copper(II) bromide
aDepartment of Inorganic Chemistry, Faculty of Chemistry, Gdansk University of Technology, 11/12 G. Narutowicz Street, 80233-PL Gdańsk, Poland, and bFachbereich Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger Strasse 54, 67663 Kaiserslautern, Germany
*Correspondence e-mail: anndoleg@pg.gda.pl
The CuII ion in the title molecular salt, [CuBr(C5H8N2)4]Br, is coordinated in a square-pyramidal geometry by four N atoms of imidazole ligands and one bromide anion in the apical position. In the crystal, the ions are linked by N—H⋯Br hydrogen bonds involving both the coordinating and the free bromide species as acceptors. A C—H⋯Br interaction is also observed. Overall, a three-dimensional network results.
Related literature
For more copper(II) complexes with bromido and imidazole ligands, see: Godlewska et al. (2011); Hossaini Sadr et al. (2004); Li et al. (2007); Liu et al. (2007); Näther et al. (2002a,b); Parker & Breneman (1995).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812047447/hb6993sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047447/hb6993Isup2.hkl
The title compound was prepared by adding a solution of 0.223 g (1 mmol) copper(II) bromide in 4 ml of methanol to a solution of 0.433 g (4.5 mmol) 2-ethylimidazole in 2 ml of methanol. After few days violet crystals were obtained by slow evaporation of solvent from the reaction mixture.
All C–H hydrogen atoms were refined as riding on carbon atoms with methyl C–H = 0.99 Å, methylene C–H = 0.98 Å, aromatic C–H = 0.95 Å and Uiso(H)=1.5Ueq(C) for methyl groups and 1.2 Ueq(C) for the rest of H atoms.
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).[CuBr(C5H8N2)4]Br | F(000) = 1228 |
Mr = 607.90 | Dx = 1.584 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2yn | Cell parameters from 6482 reflections |
a = 10.1771 (2) Å | θ = 3.5–62.6° |
b = 19.9230 (3) Å | µ = 5.06 mm−1 |
c = 12.5723 (2) Å | T = 150 K |
β = 90.386 (2)° | Indifferent fragment, violet |
V = 2549.08 (8) Å3 | 0.21 × 0.20 × 0.05 mm |
Z = 4 |
Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) diffractometer | 4058 independent reflections |
Radiation source: fine-focus sealed tube | 3719 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.020 |
Detector resolution: 16.1399 pixels mm-1 | θmax = 62.7°, θmin = 4.2° |
ω scans | h = −11→10 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −22→18 |
Tmin = 0.416, Tmax = 0.786 | l = −14→10 |
9229 measured reflections |
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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0323P)2 + 1.0444P] where P = (Fo2 + 2Fc2)/3 |
4058 reflections | (Δ/σ)max = 0.002 |
284 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
[CuBr(C5H8N2)4]Br | V = 2549.08 (8) Å3 |
Mr = 607.90 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 10.1771 (2) Å | µ = 5.06 mm−1 |
b = 19.9230 (3) Å | T = 150 K |
c = 12.5723 (2) Å | 0.21 × 0.20 × 0.05 mm |
β = 90.386 (2)° |
Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) diffractometer | 4058 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 3719 reflections with I > 2σ(I) |
Tmin = 0.416, Tmax = 0.786 | Rint = 0.020 |
9229 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.42 e Å−3 |
4058 reflections | Δρmin = −0.34 e Å−3 |
284 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.24721 (3) | 0.861967 (16) | 0.79905 (3) | 0.01634 (9) | |
Br1 | 0.23840 (2) | 0.845061 (13) | 1.036999 (19) | 0.02191 (8) | |
N1 | 0.08773 (19) | 0.80290 (10) | 0.77538 (16) | 0.0205 (4) | |
N2 | −0.0633 (2) | 0.73282 (11) | 0.71786 (18) | 0.0298 (5) | |
H2 | −0.1047 | 0.7035 | 0.6774 | 0.036* | |
C1 | −0.0142 (2) | 0.80070 (13) | 0.8483 (2) | 0.0257 (6) | |
H1 | −0.0181 | 0.8257 | 0.9126 | 0.031* | |
C2 | −0.1070 (3) | 0.75730 (14) | 0.8132 (2) | 0.0321 (6) | |
H2A | −0.1867 | 0.7460 | 0.8478 | 0.038* | |
C3 | 0.0542 (2) | 0.76125 (12) | 0.6966 (2) | 0.0235 (5) | |
C4 | 0.1271 (3) | 0.74770 (14) | 0.5965 (2) | 0.0284 (6) | |
H4A | 0.1946 | 0.7829 | 0.5871 | 0.034* | |
H4B | 0.0651 | 0.7507 | 0.5357 | 0.034* | |
C5 | 0.1940 (3) | 0.67900 (15) | 0.5945 (2) | 0.0376 (7) | |
H5A | 0.2570 | 0.6759 | 0.6536 | 0.056* | |
H5B | 0.2403 | 0.6734 | 0.5270 | 0.056* | |
H5C | 0.1276 | 0.6437 | 0.6016 | 0.056* | |
N3 | 0.12993 (18) | 0.94198 (10) | 0.79926 (15) | 0.0185 (4) | |
N4 | −0.0231 (2) | 1.01429 (10) | 0.75619 (17) | 0.0234 (5) | |
H4 | −0.0838 | 1.0353 | 0.7188 | 0.028* | |
C6 | 0.1095 (2) | 0.98466 (12) | 0.8846 (2) | 0.0244 (5) | |
H6 | 0.1547 | 0.9829 | 0.9509 | 0.029* | |
C7 | 0.0141 (3) | 1.02935 (13) | 0.8579 (2) | 0.0271 (6) | |
H7 | −0.0200 | 1.0642 | 0.9013 | 0.033* | |
C8 | 0.0490 (2) | 0.96163 (12) | 0.72257 (19) | 0.0192 (5) | |
C9 | 0.0401 (3) | 0.93264 (13) | 0.6135 (2) | 0.0270 (6) | |
H9A | 0.1069 | 0.8968 | 0.6062 | 0.032* | |
H9B | 0.0604 | 0.9681 | 0.5609 | 0.032* | |
C10 | −0.0951 (3) | 0.90355 (15) | 0.5886 (3) | 0.0417 (8) | |
H10A | −0.1172 | 0.8695 | 0.6418 | 0.063* | |
H10B | −0.0943 | 0.8829 | 0.5178 | 0.063* | |
H10C | −0.1608 | 0.9395 | 0.5900 | 0.063* | |
N5 | 0.40712 (19) | 0.92118 (10) | 0.81018 (16) | 0.0208 (4) | |
N6 | 0.5637 (2) | 0.99454 (12) | 0.78382 (19) | 0.0340 (6) | |
H6A | 0.6086 | 1.0277 | 0.7556 | 0.041* | |
C11 | 0.5028 (3) | 0.91305 (14) | 0.8881 (2) | 0.0323 (6) | |
H11 | 0.5007 | 0.8808 | 0.9437 | 0.039* | |
C12 | 0.5992 (3) | 0.95818 (17) | 0.8722 (2) | 0.0414 (8) | |
H12 | 0.6766 | 0.9638 | 0.9140 | 0.050* | |
C13 | 0.4484 (2) | 0.97063 (12) | 0.7479 (2) | 0.0227 (5) | |
C14 | 0.3819 (3) | 0.99879 (13) | 0.6518 (2) | 0.0268 (6) | |
H14A | 0.3141 | 0.9667 | 0.6268 | 0.032* | |
H14B | 0.4473 | 1.0039 | 0.5944 | 0.032* | |
C15 | 0.3173 (3) | 1.06667 (14) | 0.6727 (2) | 0.0355 (7) | |
H15A | 0.2571 | 1.0627 | 0.7329 | 0.053* | |
H15B | 0.2681 | 1.0808 | 0.6093 | 0.053* | |
H15C | 0.3851 | 1.1000 | 0.6893 | 0.053* | |
N7 | 0.36498 (18) | 0.78339 (10) | 0.77723 (16) | 0.0189 (4) | |
N8 | 0.5199 (2) | 0.71775 (11) | 0.71834 (18) | 0.0270 (5) | |
H8 | 0.5820 | 0.7013 | 0.6776 | 0.032* | |
C16 | 0.3837 (2) | 0.73151 (12) | 0.8490 (2) | 0.0245 (5) | |
H16 | 0.3364 | 0.7253 | 0.9132 | 0.029* | |
C17 | 0.4800 (3) | 0.69128 (13) | 0.8130 (2) | 0.0302 (6) | |
H17 | 0.5136 | 0.6522 | 0.8467 | 0.036* | |
C18 | 0.4486 (2) | 0.77323 (13) | 0.6977 (2) | 0.0237 (5) | |
C19 | 0.4629 (3) | 0.81532 (15) | 0.6011 (2) | 0.0340 (6) | |
H19A | 0.3952 | 0.8510 | 0.6017 | 0.041* | |
H19B | 0.4476 | 0.7872 | 0.5373 | 0.041* | |
C20 | 0.5988 (3) | 0.84754 (18) | 0.5942 (3) | 0.0557 (10) | |
H20A | 0.6180 | 0.8718 | 0.6603 | 0.084* | |
H20B | 0.6005 | 0.8790 | 0.5342 | 0.084* | |
H20C | 0.6651 | 0.8126 | 0.5835 | 0.084* | |
Br2 | 0.73566 (2) | 1.087768 (13) | 0.61807 (2) | 0.02419 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.01598 (17) | 0.01449 (17) | 0.01854 (18) | 0.00071 (13) | −0.00093 (13) | 0.00029 (13) |
Br1 | 0.02224 (14) | 0.02382 (14) | 0.01968 (14) | 0.00267 (10) | 0.00118 (10) | 0.00369 (10) |
N1 | 0.0216 (10) | 0.0164 (10) | 0.0233 (11) | −0.0011 (8) | −0.0030 (8) | 0.0007 (8) |
N2 | 0.0298 (12) | 0.0262 (12) | 0.0333 (13) | −0.0099 (10) | −0.0089 (10) | −0.0016 (10) |
C1 | 0.0244 (13) | 0.0288 (14) | 0.0240 (13) | −0.0035 (11) | 0.0002 (10) | 0.0001 (11) |
C2 | 0.0276 (14) | 0.0350 (15) | 0.0336 (15) | −0.0101 (12) | −0.0004 (12) | 0.0033 (13) |
C3 | 0.0247 (13) | 0.0185 (12) | 0.0272 (13) | −0.0005 (10) | −0.0082 (10) | 0.0025 (10) |
C4 | 0.0325 (14) | 0.0301 (14) | 0.0226 (13) | 0.0025 (12) | −0.0063 (11) | −0.0050 (11) |
C5 | 0.0433 (17) | 0.0336 (16) | 0.0359 (16) | 0.0049 (13) | −0.0065 (13) | −0.0115 (13) |
N3 | 0.0187 (10) | 0.0160 (10) | 0.0208 (10) | −0.0006 (8) | −0.0001 (8) | 0.0006 (8) |
N4 | 0.0228 (10) | 0.0220 (11) | 0.0253 (11) | 0.0072 (9) | −0.0009 (9) | 0.0045 (9) |
C6 | 0.0334 (14) | 0.0208 (13) | 0.0190 (13) | 0.0033 (11) | 0.0009 (10) | −0.0029 (10) |
C7 | 0.0346 (14) | 0.0221 (13) | 0.0247 (13) | 0.0080 (11) | 0.0042 (11) | −0.0015 (11) |
C8 | 0.0187 (12) | 0.0172 (12) | 0.0218 (12) | −0.0002 (10) | −0.0006 (10) | 0.0026 (10) |
C9 | 0.0326 (14) | 0.0262 (14) | 0.0222 (13) | 0.0048 (11) | −0.0035 (11) | 0.0026 (11) |
C10 | 0.0432 (17) | 0.0373 (17) | 0.0443 (18) | 0.0062 (14) | −0.0207 (14) | −0.0104 (14) |
N5 | 0.0184 (10) | 0.0196 (10) | 0.0243 (11) | −0.0007 (8) | 0.0001 (8) | 0.0020 (9) |
N6 | 0.0286 (12) | 0.0348 (13) | 0.0384 (14) | −0.0148 (10) | −0.0038 (10) | 0.0108 (11) |
C11 | 0.0269 (14) | 0.0379 (16) | 0.0320 (15) | −0.0047 (12) | −0.0083 (12) | 0.0128 (13) |
C12 | 0.0294 (15) | 0.055 (2) | 0.0393 (17) | −0.0153 (14) | −0.0138 (13) | 0.0157 (15) |
C13 | 0.0212 (12) | 0.0240 (13) | 0.0230 (13) | −0.0013 (10) | 0.0024 (10) | −0.0025 (10) |
C14 | 0.0288 (14) | 0.0273 (14) | 0.0243 (14) | −0.0023 (11) | 0.0034 (11) | 0.0047 (11) |
C15 | 0.0418 (16) | 0.0286 (15) | 0.0362 (16) | 0.0019 (13) | 0.0009 (13) | 0.0108 (13) |
N7 | 0.0191 (10) | 0.0164 (10) | 0.0213 (10) | 0.0017 (8) | 0.0003 (8) | 0.0000 (8) |
N8 | 0.0240 (11) | 0.0256 (12) | 0.0314 (12) | 0.0075 (9) | 0.0041 (9) | −0.0071 (10) |
C16 | 0.0290 (13) | 0.0213 (13) | 0.0231 (13) | 0.0039 (11) | −0.0010 (11) | 0.0014 (10) |
C17 | 0.0371 (15) | 0.0222 (14) | 0.0311 (15) | 0.0091 (12) | −0.0040 (12) | 0.0003 (11) |
C18 | 0.0215 (12) | 0.0237 (13) | 0.0259 (13) | 0.0007 (10) | 0.0013 (10) | −0.0062 (11) |
C19 | 0.0445 (16) | 0.0313 (15) | 0.0264 (14) | 0.0022 (13) | 0.0115 (12) | −0.0002 (12) |
C20 | 0.050 (2) | 0.047 (2) | 0.070 (2) | 0.0011 (16) | 0.0324 (18) | 0.0124 (18) |
Br2 | 0.02263 (14) | 0.02361 (14) | 0.02629 (15) | −0.00013 (10) | −0.00150 (10) | 0.00541 (10) |
Cu1—N3 | 1.9914 (19) | C10—H10B | 0.9800 |
Cu1—N7 | 1.9918 (19) | C10—H10C | 0.9800 |
Cu1—N5 | 2.014 (2) | N5—C13 | 1.328 (3) |
Cu1—N1 | 2.0250 (19) | N5—C11 | 1.386 (3) |
Cu1—Br1 | 3.0125 (4) | N6—C13 | 1.341 (3) |
N1—C3 | 1.334 (3) | N6—C12 | 1.373 (4) |
N1—C1 | 1.390 (3) | N6—H6A | 0.8800 |
N2—C3 | 1.351 (3) | C11—C12 | 1.346 (4) |
N2—C2 | 1.371 (4) | C11—H11 | 0.9500 |
N2—H2 | 0.8800 | C12—H12 | 0.9500 |
C1—C2 | 1.352 (4) | C13—C14 | 1.491 (4) |
C1—H1 | 0.9500 | C14—C15 | 1.527 (4) |
C2—H2A | 0.9500 | C14—H14A | 0.9900 |
C3—C4 | 1.490 (4) | C14—H14B | 0.9900 |
C4—C5 | 1.529 (4) | C15—H15A | 0.9800 |
C4—H4A | 0.9900 | C15—H15B | 0.9800 |
C4—H4B | 0.9900 | C15—H15C | 0.9800 |
C5—H5A | 0.9800 | N7—C18 | 1.333 (3) |
C5—H5B | 0.9800 | N7—C16 | 1.385 (3) |
C5—H5C | 0.9800 | N8—C18 | 1.347 (3) |
N3—C8 | 1.323 (3) | N8—C17 | 1.365 (4) |
N3—C6 | 1.386 (3) | N8—H8 | 0.8800 |
N4—C8 | 1.350 (3) | C16—C17 | 1.348 (4) |
N4—C7 | 1.364 (3) | C16—H16 | 0.9500 |
N4—H4 | 0.8800 | C17—H17 | 0.9500 |
C6—C7 | 1.358 (4) | C18—C19 | 1.483 (4) |
C6—H6 | 0.9500 | C19—C20 | 1.528 (4) |
C7—H7 | 0.9500 | C19—H19A | 0.9900 |
C8—C9 | 1.490 (4) | C19—H19B | 0.9900 |
C9—C10 | 1.524 (4) | C20—H20A | 0.9800 |
C9—H9A | 0.9900 | C20—H20B | 0.9800 |
C9—H9B | 0.9900 | C20—H20C | 0.9800 |
C10—H10A | 0.9800 | ||
N3—Cu1—N7 | 172.13 (8) | C9—C10—H10B | 109.5 |
N3—Cu1—N5 | 90.87 (8) | H10A—C10—H10B | 109.5 |
N7—Cu1—N5 | 89.04 (8) | C9—C10—H10C | 109.5 |
N3—Cu1—N1 | 89.17 (8) | H10A—C10—H10C | 109.5 |
N7—Cu1—N1 | 90.31 (8) | H10B—C10—H10C | 109.5 |
N5—Cu1—N1 | 175.54 (8) | C13—N5—C11 | 106.2 (2) |
N3—Cu1—Br1 | 93.80 (6) | C13—N5—Cu1 | 130.70 (17) |
N7—Cu1—Br1 | 94.06 (6) | C11—N5—Cu1 | 122.98 (17) |
N5—Cu1—Br1 | 91.48 (6) | C13—N6—C12 | 108.1 (2) |
N1—Cu1—Br1 | 92.97 (6) | C13—N6—H6A | 126.0 |
C3—N1—C1 | 106.4 (2) | C12—N6—H6A | 126.0 |
C3—N1—Cu1 | 132.14 (17) | C12—C11—N5 | 109.1 (2) |
C1—N1—Cu1 | 121.50 (16) | C12—C11—H11 | 125.5 |
C3—N2—C2 | 108.4 (2) | N5—C11—H11 | 125.5 |
C3—N2—H2 | 125.8 | C11—C12—N6 | 106.5 (2) |
C2—N2—H2 | 125.8 | C11—C12—H12 | 126.8 |
C2—C1—N1 | 109.1 (2) | N6—C12—H12 | 126.8 |
C2—C1—H1 | 125.4 | N5—C13—N6 | 110.1 (2) |
N1—C1—H1 | 125.4 | N5—C13—C14 | 127.8 (2) |
C1—C2—N2 | 106.4 (2) | N6—C13—C14 | 122.0 (2) |
C1—C2—H2A | 126.8 | C13—C14—C15 | 112.8 (2) |
N2—C2—H2A | 126.8 | C13—C14—H14A | 109.0 |
N1—C3—N2 | 109.6 (2) | C15—C14—H14A | 109.0 |
N1—C3—C4 | 127.8 (2) | C13—C14—H14B | 109.0 |
N2—C3—C4 | 122.5 (2) | C15—C14—H14B | 109.0 |
C3—C4—C5 | 113.6 (2) | H14A—C14—H14B | 107.8 |
C3—C4—H4A | 108.8 | C14—C15—H15A | 109.5 |
C5—C4—H4A | 108.8 | C14—C15—H15B | 109.5 |
C3—C4—H4B | 108.8 | H15A—C15—H15B | 109.5 |
C5—C4—H4B | 108.8 | C14—C15—H15C | 109.5 |
H4A—C4—H4B | 107.7 | H15A—C15—H15C | 109.5 |
C4—C5—H5A | 109.5 | H15B—C15—H15C | 109.5 |
C4—C5—H5B | 109.5 | C18—N7—C16 | 106.9 (2) |
H5A—C5—H5B | 109.5 | C18—N7—Cu1 | 127.62 (17) |
C4—C5—H5C | 109.5 | C16—N7—Cu1 | 125.24 (16) |
H5A—C5—H5C | 109.5 | C18—N8—C17 | 108.8 (2) |
H5B—C5—H5C | 109.5 | C18—N8—H8 | 125.6 |
C8—N3—C6 | 106.7 (2) | C17—N8—H8 | 125.6 |
C8—N3—Cu1 | 127.30 (16) | C17—C16—N7 | 108.8 (2) |
C6—N3—Cu1 | 125.82 (16) | C17—C16—H16 | 125.6 |
C8—N4—C7 | 108.5 (2) | N7—C16—H16 | 125.6 |
C8—N4—H4 | 125.8 | C16—C17—N8 | 106.5 (2) |
C7—N4—H4 | 125.8 | C16—C17—H17 | 126.7 |
C7—C6—N3 | 108.7 (2) | N8—C17—H17 | 126.7 |
C7—C6—H6 | 125.6 | N7—C18—N8 | 109.0 (2) |
N3—C6—H6 | 125.6 | N7—C18—C19 | 126.5 (2) |
C6—C7—N4 | 106.3 (2) | N8—C18—C19 | 124.5 (2) |
C6—C7—H7 | 126.8 | C18—C19—C20 | 112.2 (3) |
N4—C7—H7 | 126.8 | C18—C19—H19A | 109.2 |
N3—C8—N4 | 109.8 (2) | C20—C19—H19A | 109.2 |
N3—C8—C9 | 126.1 (2) | C18—C19—H19B | 109.2 |
N4—C8—C9 | 124.0 (2) | C20—C19—H19B | 109.2 |
C8—C9—C10 | 112.7 (2) | H19A—C19—H19B | 107.9 |
C8—C9—H9A | 109.1 | C19—C20—H20A | 109.5 |
C10—C9—H9A | 109.1 | C19—C20—H20B | 109.5 |
C8—C9—H9B | 109.1 | H20A—C20—H20B | 109.5 |
C10—C9—H9B | 109.1 | C19—C20—H20C | 109.5 |
H9A—C9—H9B | 107.8 | H20A—C20—H20C | 109.5 |
C9—C10—H10A | 109.5 | H20B—C20—H20C | 109.5 |
N3—Cu1—N1—C3 | 118.9 (2) | N3—Cu1—N5—C13 | −57.2 (2) |
N7—Cu1—N1—C3 | −53.2 (2) | N7—Cu1—N5—C13 | 115.0 (2) |
Br1—Cu1—N1—C3 | −147.3 (2) | Br1—Cu1—N5—C13 | −151.0 (2) |
N3—Cu1—N1—C1 | −60.63 (19) | N3—Cu1—N5—C11 | 126.8 (2) |
N7—Cu1—N1—C1 | 127.22 (19) | N7—Cu1—N5—C11 | −61.0 (2) |
Br1—Cu1—N1—C1 | 33.14 (18) | Br1—Cu1—N5—C11 | 33.0 (2) |
C3—N1—C1—C2 | 0.7 (3) | C13—N5—C11—C12 | 0.7 (3) |
Cu1—N1—C1—C2 | −179.70 (18) | Cu1—N5—C11—C12 | 177.6 (2) |
N1—C1—C2—N2 | −0.5 (3) | N5—C11—C12—N6 | −0.2 (4) |
C3—N2—C2—C1 | 0.1 (3) | C13—N6—C12—C11 | −0.5 (4) |
C1—N1—C3—N2 | −0.6 (3) | C11—N5—C13—N6 | −1.0 (3) |
Cu1—N1—C3—N2 | 179.83 (16) | Cu1—N5—C13—N6 | −177.53 (18) |
C1—N1—C3—C4 | 177.1 (2) | C11—N5—C13—C14 | 179.6 (3) |
Cu1—N1—C3—C4 | −2.5 (4) | Cu1—N5—C13—C14 | 3.0 (4) |
C2—N2—C3—N1 | 0.3 (3) | C12—N6—C13—N5 | 1.0 (3) |
C2—N2—C3—C4 | −177.5 (2) | C12—N6—C13—C14 | −179.6 (3) |
N1—C3—C4—C5 | 107.0 (3) | N5—C13—C14—C15 | 104.3 (3) |
N2—C3—C4—C5 | −75.6 (3) | N6—C13—C14—C15 | −75.1 (3) |
N5—Cu1—N3—C8 | 117.5 (2) | N5—Cu1—N7—C18 | −62.3 (2) |
N1—Cu1—N3—C8 | −58.1 (2) | N1—Cu1—N7—C18 | 113.3 (2) |
Br1—Cu1—N3—C8 | −151.00 (19) | Br1—Cu1—N7—C18 | −153.7 (2) |
N5—Cu1—N3—C6 | −68.5 (2) | N5—Cu1—N7—C16 | 111.1 (2) |
N1—Cu1—N3—C6 | 115.9 (2) | N1—Cu1—N7—C16 | −73.3 (2) |
Br1—Cu1—N3—C6 | 23.00 (19) | Br1—Cu1—N7—C16 | 19.70 (19) |
C8—N3—C6—C7 | 0.8 (3) | C18—N7—C16—C17 | 1.1 (3) |
Cu1—N3—C6—C7 | −174.24 (17) | Cu1—N7—C16—C17 | −173.44 (17) |
N3—C6—C7—N4 | −0.4 (3) | N7—C16—C17—N8 | −0.7 (3) |
C8—N4—C7—C6 | −0.2 (3) | C18—N8—C17—C16 | 0.0 (3) |
C6—N3—C8—N4 | −0.9 (3) | C16—N7—C18—N8 | −1.1 (3) |
Cu1—N3—C8—N4 | 174.05 (15) | Cu1—N7—C18—N8 | 173.31 (16) |
C6—N3—C8—C9 | 177.0 (2) | C16—N7—C18—C19 | 178.9 (2) |
Cu1—N3—C8—C9 | −8.0 (3) | Cu1—N7—C18—C19 | −6.7 (4) |
C7—N4—C8—N3 | 0.7 (3) | C17—N8—C18—N7 | 0.7 (3) |
C7—N4—C8—C9 | −177.3 (2) | C17—N8—C18—C19 | −179.3 (3) |
N3—C8—C9—C10 | 119.5 (3) | N7—C18—C19—C20 | 116.9 (3) |
N4—C8—C9—C10 | −62.9 (3) | N8—C18—C19—C20 | −63.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Br1i | 0.88 | 2.56 | 3.405 (2) | 161 |
N4—H4···Br2ii | 0.88 | 2.46 | 3.336 (2) | 176 |
N6—H6A···Br2 | 0.88 | 2.47 | 3.302 (2) | 157 |
N8—H8···Br1iii | 0.88 | 2.56 | 3.432 (2) | 172 |
C17—H17···Br2iv | 0.95 | 2.89 | 3.653 (3) | 138 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) x+1/2, −y+3/2, z−1/2; (iv) −x+3/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [CuBr(C5H8N2)4]Br |
Mr | 607.90 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 10.1771 (2), 19.9230 (3), 12.5723 (2) |
β (°) | 90.386 (2) |
V (Å3) | 2549.08 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 5.06 |
Crystal size (mm) | 0.21 × 0.20 × 0.05 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.416, 0.786 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9229, 4058, 3719 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.576 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.060, 1.05 |
No. of reflections | 4058 |
No. of parameters | 284 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.34 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cu1—N3 | 1.9914 (19) | Cu1—N1 | 2.0250 (19) |
Cu1—N7 | 1.9918 (19) | Cu1—Br1 | 3.0125 (4) |
Cu1—N5 | 2.014 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Br1i | 0.88 | 2.56 | 3.405 (2) | 161 |
N4—H4···Br2ii | 0.88 | 2.46 | 3.336 (2) | 176 |
N6—H6A···Br2 | 0.88 | 2.47 | 3.302 (2) | 157 |
N8—H8···Br1iii | 0.88 | 2.56 | 3.432 (2) | 172 |
C17—H17···Br2iv | 0.95 | 2.89 | 3.653 (3) | 138 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) x+1/2, −y+3/2, z−1/2; (iv) −x+3/2, y−1/2, −z+3/2. |
Acknowledgements
SG acknowledges the outgoing scholarship for her stay in Kaiserslautern within project No. POKL.04.01.01-00-368/09 co-financed by the European Union (the European Social Fund) and the Polish Ministry of Science and Higher Education.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound, (I), is the third in a series of similar complex compounds (Godlewska et al. (2011)). The complex cation features square pyramidal geometry around Cu atom with four N atoms in the basal plane and apical bromide ligand. The deviation of N—Cu—N angles from the values of 90 and 180 degrees are very small and such is the deviation of Cu atom (0.1077 Å) from the basal plane formed by the four nitrogen atoms of imidazole ligands. The complex cations and Br2 anions form a three-dimensional network of intervowen NH···Br and CH···Br interactions that results in a "compact" packing of the interacting species and the relatively large density of the obtained crystals.
The asymmetric unit of (I) is shown in Fig. 1 and packing diagram is presented in Fig.2.