Literature DB >> 23468738

Bromidotetra-kis-(2-ethyl-1H-imidazole-κN (3))copper(II) bromide.

Sylwia Godlewska1, Harald Kelm, Hans-Jörg Krüger, Anna Dołęga.   

Abstract

The Cu(II) ion in the title mol-ecular 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 inter-action is also observed. Overall, a three-dimensional network results.

Entities:  

Year:  2012        PMID: 23468738      PMCID: PMC3588773          DOI: 10.1107/S1600536812047447

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


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

[CuBr(C5H8N2)4]Br M = 607.90 Monoclinic, a = 10.1771 (2) Å b = 19.9230 (3) Å c = 12.5723 (2) Å β = 90.386 (2)° V = 2549.08 (8) Å3 Z = 4 Cu Kα radiation μ = 5.06 mm−1 T = 150 K 0.21 × 0.20 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.416, T max = 0.786 9229 measured reflections 4058 independent reflections 3719 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.024 wR(F 2) = 0.060 S = 1.05 4058 reflections 284 parameters H-atom parameters constrained Δρmax = 0.42 e Å−3 Δρmin = −0.34 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: 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. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047447/hb6993sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047447/hb6993Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[CuBr(C5H8N2)4]BrF(000) = 1228
Mr = 607.90Dx = 1.584 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ynCell parameters from 6482 reflections
a = 10.1771 (2) Åθ = 3.5–62.6°
b = 19.9230 (3) ŵ = 5.06 mm1
c = 12.5723 (2) ÅT = 150 K
β = 90.386 (2)°Indifferent fragment, violet
V = 2549.08 (8) Å30.21 × 0.20 × 0.05 mm
Z = 4
Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) diffractometer4058 independent reflections
Radiation source: fine-focus sealed tube3719 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.020
Detector resolution: 16.1399 pixels mm-1θmax = 62.7°, θmin = 4.2°
ω scansh = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −22→18
Tmin = 0.416, Tmax = 0.786l = −14→10
9229 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0323P)2 + 1.0444P] where P = (Fo2 + 2Fc2)/3
4058 reflections(Δ/σ)max = 0.002
284 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = −0.34 e Å3
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.
xyzUiso*/Ueq
Cu10.24721 (3)0.861967 (16)0.79905 (3)0.01634 (9)
Br10.23840 (2)0.845061 (13)1.036999 (19)0.02191 (8)
N10.08773 (19)0.80290 (10)0.77538 (16)0.0205 (4)
N2−0.0633 (2)0.73282 (11)0.71786 (18)0.0298 (5)
H2−0.10470.70350.67740.036*
C1−0.0142 (2)0.80070 (13)0.8483 (2)0.0257 (6)
H1−0.01810.82570.91260.031*
C2−0.1070 (3)0.75730 (14)0.8132 (2)0.0321 (6)
H2A−0.18670.74600.84780.038*
C30.0542 (2)0.76125 (12)0.6966 (2)0.0235 (5)
C40.1271 (3)0.74770 (14)0.5965 (2)0.0284 (6)
H4A0.19460.78290.58710.034*
H4B0.06510.75070.53570.034*
C50.1940 (3)0.67900 (15)0.5945 (2)0.0376 (7)
H5A0.25700.67590.65360.056*
H5B0.24030.67340.52700.056*
H5C0.12760.64370.60160.056*
N30.12993 (18)0.94198 (10)0.79926 (15)0.0185 (4)
N4−0.0231 (2)1.01429 (10)0.75619 (17)0.0234 (5)
H4−0.08381.03530.71880.028*
C60.1095 (2)0.98466 (12)0.8846 (2)0.0244 (5)
H60.15470.98290.95090.029*
C70.0141 (3)1.02935 (13)0.8579 (2)0.0271 (6)
H7−0.02001.06420.90130.033*
C80.0490 (2)0.96163 (12)0.72257 (19)0.0192 (5)
C90.0401 (3)0.93264 (13)0.6135 (2)0.0270 (6)
H9A0.10690.89680.60620.032*
H9B0.06040.96810.56090.032*
C10−0.0951 (3)0.90355 (15)0.5886 (3)0.0417 (8)
H10A−0.11720.86950.64180.063*
H10B−0.09430.88290.51780.063*
H10C−0.16080.93950.59000.063*
N50.40712 (19)0.92118 (10)0.81018 (16)0.0208 (4)
N60.5637 (2)0.99454 (12)0.78382 (19)0.0340 (6)
H6A0.60861.02770.75560.041*
C110.5028 (3)0.91305 (14)0.8881 (2)0.0323 (6)
H110.50070.88080.94370.039*
C120.5992 (3)0.95818 (17)0.8722 (2)0.0414 (8)
H120.67660.96380.91400.050*
C130.4484 (2)0.97063 (12)0.7479 (2)0.0227 (5)
C140.3819 (3)0.99879 (13)0.6518 (2)0.0268 (6)
H14A0.31410.96670.62680.032*
H14B0.44731.00390.59440.032*
C150.3173 (3)1.06667 (14)0.6727 (2)0.0355 (7)
H15A0.25711.06270.73290.053*
H15B0.26811.08080.60930.053*
H15C0.38511.10000.68930.053*
N70.36498 (18)0.78339 (10)0.77723 (16)0.0189 (4)
N80.5199 (2)0.71775 (11)0.71834 (18)0.0270 (5)
H80.58200.70130.67760.032*
C160.3837 (2)0.73151 (12)0.8490 (2)0.0245 (5)
H160.33640.72530.91320.029*
C170.4800 (3)0.69128 (13)0.8130 (2)0.0302 (6)
H170.51360.65220.84670.036*
C180.4486 (2)0.77323 (13)0.6977 (2)0.0237 (5)
C190.4629 (3)0.81532 (15)0.6011 (2)0.0340 (6)
H19A0.39520.85100.60170.041*
H19B0.44760.78720.53730.041*
C200.5988 (3)0.84754 (18)0.5942 (3)0.0557 (10)
H20A0.61800.87180.66030.084*
H20B0.60050.87900.53420.084*
H20C0.66510.81260.58350.084*
Br20.73566 (2)1.087768 (13)0.61807 (2)0.02419 (8)
U11U22U33U12U13U23
Cu10.01598 (17)0.01449 (17)0.01854 (18)0.00071 (13)−0.00093 (13)0.00029 (13)
Br10.02224 (14)0.02382 (14)0.01968 (14)0.00267 (10)0.00118 (10)0.00369 (10)
N10.0216 (10)0.0164 (10)0.0233 (11)−0.0011 (8)−0.0030 (8)0.0007 (8)
N20.0298 (12)0.0262 (12)0.0333 (13)−0.0099 (10)−0.0089 (10)−0.0016 (10)
C10.0244 (13)0.0288 (14)0.0240 (13)−0.0035 (11)0.0002 (10)0.0001 (11)
C20.0276 (14)0.0350 (15)0.0336 (15)−0.0101 (12)−0.0004 (12)0.0033 (13)
C30.0247 (13)0.0185 (12)0.0272 (13)−0.0005 (10)−0.0082 (10)0.0025 (10)
C40.0325 (14)0.0301 (14)0.0226 (13)0.0025 (12)−0.0063 (11)−0.0050 (11)
C50.0433 (17)0.0336 (16)0.0359 (16)0.0049 (13)−0.0065 (13)−0.0115 (13)
N30.0187 (10)0.0160 (10)0.0208 (10)−0.0006 (8)−0.0001 (8)0.0006 (8)
N40.0228 (10)0.0220 (11)0.0253 (11)0.0072 (9)−0.0009 (9)0.0045 (9)
C60.0334 (14)0.0208 (13)0.0190 (13)0.0033 (11)0.0009 (10)−0.0029 (10)
C70.0346 (14)0.0221 (13)0.0247 (13)0.0080 (11)0.0042 (11)−0.0015 (11)
C80.0187 (12)0.0172 (12)0.0218 (12)−0.0002 (10)−0.0006 (10)0.0026 (10)
C90.0326 (14)0.0262 (14)0.0222 (13)0.0048 (11)−0.0035 (11)0.0026 (11)
C100.0432 (17)0.0373 (17)0.0443 (18)0.0062 (14)−0.0207 (14)−0.0104 (14)
N50.0184 (10)0.0196 (10)0.0243 (11)−0.0007 (8)0.0001 (8)0.0020 (9)
N60.0286 (12)0.0348 (13)0.0384 (14)−0.0148 (10)−0.0038 (10)0.0108 (11)
C110.0269 (14)0.0379 (16)0.0320 (15)−0.0047 (12)−0.0083 (12)0.0128 (13)
C120.0294 (15)0.055 (2)0.0393 (17)−0.0153 (14)−0.0138 (13)0.0157 (15)
C130.0212 (12)0.0240 (13)0.0230 (13)−0.0013 (10)0.0024 (10)−0.0025 (10)
C140.0288 (14)0.0273 (14)0.0243 (14)−0.0023 (11)0.0034 (11)0.0047 (11)
C150.0418 (16)0.0286 (15)0.0362 (16)0.0019 (13)0.0009 (13)0.0108 (13)
N70.0191 (10)0.0164 (10)0.0213 (10)0.0017 (8)0.0003 (8)0.0000 (8)
N80.0240 (11)0.0256 (12)0.0314 (12)0.0075 (9)0.0041 (9)−0.0071 (10)
C160.0290 (13)0.0213 (13)0.0231 (13)0.0039 (11)−0.0010 (11)0.0014 (10)
C170.0371 (15)0.0222 (14)0.0311 (15)0.0091 (12)−0.0040 (12)0.0003 (11)
C180.0215 (12)0.0237 (13)0.0259 (13)0.0007 (10)0.0013 (10)−0.0062 (11)
C190.0445 (16)0.0313 (15)0.0264 (14)0.0022 (13)0.0115 (12)−0.0002 (12)
C200.050 (2)0.047 (2)0.070 (2)0.0011 (16)0.0324 (18)0.0124 (18)
Br20.02263 (14)0.02361 (14)0.02629 (15)−0.00013 (10)−0.00150 (10)0.00541 (10)
Cu1—N31.9914 (19)C10—H10B0.9800
Cu1—N71.9918 (19)C10—H10C0.9800
Cu1—N52.014 (2)N5—C131.328 (3)
Cu1—N12.0250 (19)N5—C111.386 (3)
Cu1—Br13.0125 (4)N6—C131.341 (3)
N1—C31.334 (3)N6—C121.373 (4)
N1—C11.390 (3)N6—H6A0.8800
N2—C31.351 (3)C11—C121.346 (4)
N2—C21.371 (4)C11—H110.9500
N2—H20.8800C12—H120.9500
C1—C21.352 (4)C13—C141.491 (4)
C1—H10.9500C14—C151.527 (4)
C2—H2A0.9500C14—H14A0.9900
C3—C41.490 (4)C14—H14B0.9900
C4—C51.529 (4)C15—H15A0.9800
C4—H4A0.9900C15—H15B0.9800
C4—H4B0.9900C15—H15C0.9800
C5—H5A0.9800N7—C181.333 (3)
C5—H5B0.9800N7—C161.385 (3)
C5—H5C0.9800N8—C181.347 (3)
N3—C81.323 (3)N8—C171.365 (4)
N3—C61.386 (3)N8—H80.8800
N4—C81.350 (3)C16—C171.348 (4)
N4—C71.364 (3)C16—H160.9500
N4—H40.8800C17—H170.9500
C6—C71.358 (4)C18—C191.483 (4)
C6—H60.9500C19—C201.528 (4)
C7—H70.9500C19—H19A0.9900
C8—C91.490 (4)C19—H19B0.9900
C9—C101.524 (4)C20—H20A0.9800
C9—H9A0.9900C20—H20B0.9800
C9—H9B0.9900C20—H20C0.9800
C10—H10A0.9800
N3—Cu1—N7172.13 (8)C9—C10—H10B109.5
N3—Cu1—N590.87 (8)H10A—C10—H10B109.5
N7—Cu1—N589.04 (8)C9—C10—H10C109.5
N3—Cu1—N189.17 (8)H10A—C10—H10C109.5
N7—Cu1—N190.31 (8)H10B—C10—H10C109.5
N5—Cu1—N1175.54 (8)C13—N5—C11106.2 (2)
N3—Cu1—Br193.80 (6)C13—N5—Cu1130.70 (17)
N7—Cu1—Br194.06 (6)C11—N5—Cu1122.98 (17)
N5—Cu1—Br191.48 (6)C13—N6—C12108.1 (2)
N1—Cu1—Br192.97 (6)C13—N6—H6A126.0
C3—N1—C1106.4 (2)C12—N6—H6A126.0
C3—N1—Cu1132.14 (17)C12—C11—N5109.1 (2)
C1—N1—Cu1121.50 (16)C12—C11—H11125.5
C3—N2—C2108.4 (2)N5—C11—H11125.5
C3—N2—H2125.8C11—C12—N6106.5 (2)
C2—N2—H2125.8C11—C12—H12126.8
C2—C1—N1109.1 (2)N6—C12—H12126.8
C2—C1—H1125.4N5—C13—N6110.1 (2)
N1—C1—H1125.4N5—C13—C14127.8 (2)
C1—C2—N2106.4 (2)N6—C13—C14122.0 (2)
C1—C2—H2A126.8C13—C14—C15112.8 (2)
N2—C2—H2A126.8C13—C14—H14A109.0
N1—C3—N2109.6 (2)C15—C14—H14A109.0
N1—C3—C4127.8 (2)C13—C14—H14B109.0
N2—C3—C4122.5 (2)C15—C14—H14B109.0
C3—C4—C5113.6 (2)H14A—C14—H14B107.8
C3—C4—H4A108.8C14—C15—H15A109.5
C5—C4—H4A108.8C14—C15—H15B109.5
C3—C4—H4B108.8H15A—C15—H15B109.5
C5—C4—H4B108.8C14—C15—H15C109.5
H4A—C4—H4B107.7H15A—C15—H15C109.5
C4—C5—H5A109.5H15B—C15—H15C109.5
C4—C5—H5B109.5C18—N7—C16106.9 (2)
H5A—C5—H5B109.5C18—N7—Cu1127.62 (17)
C4—C5—H5C109.5C16—N7—Cu1125.24 (16)
H5A—C5—H5C109.5C18—N8—C17108.8 (2)
H5B—C5—H5C109.5C18—N8—H8125.6
C8—N3—C6106.7 (2)C17—N8—H8125.6
C8—N3—Cu1127.30 (16)C17—C16—N7108.8 (2)
C6—N3—Cu1125.82 (16)C17—C16—H16125.6
C8—N4—C7108.5 (2)N7—C16—H16125.6
C8—N4—H4125.8C16—C17—N8106.5 (2)
C7—N4—H4125.8C16—C17—H17126.7
C7—C6—N3108.7 (2)N8—C17—H17126.7
C7—C6—H6125.6N7—C18—N8109.0 (2)
N3—C6—H6125.6N7—C18—C19126.5 (2)
C6—C7—N4106.3 (2)N8—C18—C19124.5 (2)
C6—C7—H7126.8C18—C19—C20112.2 (3)
N4—C7—H7126.8C18—C19—H19A109.2
N3—C8—N4109.8 (2)C20—C19—H19A109.2
N3—C8—C9126.1 (2)C18—C19—H19B109.2
N4—C8—C9124.0 (2)C20—C19—H19B109.2
C8—C9—C10112.7 (2)H19A—C19—H19B107.9
C8—C9—H9A109.1C19—C20—H20A109.5
C10—C9—H9A109.1C19—C20—H20B109.5
C8—C9—H9B109.1H20A—C20—H20B109.5
C10—C9—H9B109.1C19—C20—H20C109.5
H9A—C9—H9B107.8H20A—C20—H20C109.5
C9—C10—H10A109.5H20B—C20—H20C109.5
N3—Cu1—N1—C3118.9 (2)N3—Cu1—N5—C13−57.2 (2)
N7—Cu1—N1—C3−53.2 (2)N7—Cu1—N5—C13115.0 (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—C11126.8 (2)
N7—Cu1—N1—C1127.22 (19)N7—Cu1—N5—C11−61.0 (2)
Br1—Cu1—N1—C133.14 (18)Br1—Cu1—N5—C1133.0 (2)
C3—N1—C1—C20.7 (3)C13—N5—C11—C120.7 (3)
Cu1—N1—C1—C2−179.70 (18)Cu1—N5—C11—C12177.6 (2)
N1—C1—C2—N2−0.5 (3)N5—C11—C12—N6−0.2 (4)
C3—N2—C2—C10.1 (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—N2179.83 (16)Cu1—N5—C13—N6−177.53 (18)
C1—N1—C3—C4177.1 (2)C11—N5—C13—C14179.6 (3)
Cu1—N1—C3—C4−2.5 (4)Cu1—N5—C13—C143.0 (4)
C2—N2—C3—N10.3 (3)C12—N6—C13—N51.0 (3)
C2—N2—C3—C4−177.5 (2)C12—N6—C13—C14−179.6 (3)
N1—C3—C4—C5107.0 (3)N5—C13—C14—C15104.3 (3)
N2—C3—C4—C5−75.6 (3)N6—C13—C14—C15−75.1 (3)
N5—Cu1—N3—C8117.5 (2)N5—Cu1—N7—C18−62.3 (2)
N1—Cu1—N3—C8−58.1 (2)N1—Cu1—N7—C18113.3 (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—C16111.1 (2)
N1—Cu1—N3—C6115.9 (2)N1—Cu1—N7—C16−73.3 (2)
Br1—Cu1—N3—C623.00 (19)Br1—Cu1—N7—C1619.70 (19)
C8—N3—C6—C70.8 (3)C18—N7—C16—C171.1 (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—C160.0 (3)
C6—N3—C8—N4−0.9 (3)C16—N7—C18—N8−1.1 (3)
Cu1—N3—C8—N4174.05 (15)Cu1—N7—C18—N8173.31 (16)
C6—N3—C8—C9177.0 (2)C16—N7—C18—C19178.9 (2)
Cu1—N3—C8—C9−8.0 (3)Cu1—N7—C18—C19−6.7 (4)
C7—N4—C8—N30.7 (3)C17—N8—C18—N70.7 (3)
C7—N4—C8—C9−177.3 (2)C17—N8—C18—C19−179.3 (3)
N3—C8—C9—C10119.5 (3)N7—C18—C19—C20116.9 (3)
N4—C8—C9—C10−62.9 (3)N8—C18—C19—C20−63.1 (4)
D—H···AD—HH···AD···AD—H···A
N2—H2···Br1i0.882.563.405 (2)161
N4—H4···Br2ii0.882.463.336 (2)176
N6—H6A···Br20.882.473.302 (2)157
N8—H8···Br1iii0.882.563.432 (2)172
C17—H17···Br2iv0.952.893.653 (3)138
Table 1

Selected bond lengths (Å)

Cu1—N31.9914 (19)
Cu1—N71.9918 (19)
Cu1—N52.014 (2)
Cu1—N12.0250 (19)
Cu1—Br13.0125 (4)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
N2—H2⋯Br1i 0.882.563.405 (2)161
N4—H4⋯Br2ii 0.882.463.336 (2)176
N6—H6A⋯Br20.882.473.302 (2)157
N8—H8⋯Br1iii 0.882.563.432 (2)172
C17—H17⋯Br2iv 0.952.893.653 (3)138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Bromidotetra-kis-(2-isopropyl-1H-imidazole-κN)copper(II) bromide.

Authors:  Sylwia Godlewska; Joanna Socha; Katarzyna Baranowska; Anna Dołęga
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-09-14
  2 in total
  1 in total

1.  Etude structurale et vibrationnelle d'un nouveau composé complexe de cobalt: [Co(imidazole)4Cl]Cl.

Authors:  Amira Derbel; Tahar Mhiri; Mohsen Graia
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-09-17
  1 in total

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