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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m934.
Published online 2009 July 18. doi:  10.1107/S1600536809027111
PMCID: PMC2977398

Chlorido(pentane-2,4-dionato-κ2 O,O′)(1,10-phenanthroline-κ2 N,N′)copper(II)

Abstract

The CuII atom in the title compound, [Cu(C5H7O2)Cl(C12H8N2)], shows a distorted square-planar coordination; the chelating N and O atoms occupy the basal sites and the Cl atom the apical site. The square-pyramidal character along the Berry D 3hC 4v pseudorotation pathway is 92%.

Related literature

For the synthesis and electronic spectrum, see: Kwik & Ang (1978 [triangle]). For isostructural CuBr(C12H8N2)(C5H7O2), see: Onawumi et al. (2008 [triangle]).

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Object name is e-65-0m934-scheme1.jpg

Experimental

Crystal data

  • [Cu(C5H7O2)Cl(C12H8N2)]
  • M r = 378.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m934-efi1.jpg
  • a = 7.5436 (1) Å
  • b = 9.0347 (2) Å
  • c = 11.9399 (2) Å
  • α = 85.638 (1)°
  • β = 72.329 (1)°
  • γ = 85.716 (1)°
  • V = 771.97 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.60 mm−1
  • T = 163 K
  • 0.35 × 0.35 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.605, T max = 0.796
  • 5384 measured reflections
  • 3406 independent reflections
  • 3151 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.073
  • S = 1.03
  • 3406 reflections
  • 210 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027111/xu2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027111/xu2552Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank MOSTI (grant No. 02-02-11-SF0033) and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Copper chloride dihydrate (0.17 g, 1 mmol) and 1,10-phenanthroline monohydrate (0.20 g, 1 mmol) were reacted in a 1:1 v/v methanol-water mixture (5 ml) to give a light green precipitate. The copper dichloride.phenanthroline adduct (0.047 g, 0.15 mmol) was dissolved in a methanol-water mixture (5 ml) and this was treated with excess acetylacetone (5 ml) and 0.1 M sodium hydroxide (5 ml). The dark green solution was heated at 343 K for 30 min. Bluish-green crystals separated from the cool solution.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid (Barbour, 2001) plot of CuCl(C12H8N2)(C5H7O2) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.

Crystal data

[Cu(C5H7O2)Cl(C12H8N2)]Z = 2
Mr = 378.30F(000) = 386
Triclinic, P1Dx = 1.627 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5436 (1) ÅCell parameters from 4297 reflections
b = 9.0347 (2) Åθ = 2.8–28.3°
c = 11.9399 (2) ŵ = 1.60 mm1
α = 85.638 (1)°T = 163 K
β = 72.329 (1)°Block, blue
γ = 85.716 (1)°0.35 × 0.35 × 0.15 mm
V = 771.97 (2) Å3

Data collection

Bruker SMART APEX diffractometer3406 independent reflections
Radiation source: fine-focus sealed tube3151 reflections with I > 2σ(I)
graphiteRint = 0.015
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.605, Tmax = 0.796k = −11→11
5384 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0226P)2 + 1.0753P] where P = (Fo2 + 2Fc2)/3
3406 reflections(Δ/σ)max = 0.001
210 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.43 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cu10.74448 (4)0.62243 (3)0.25532 (2)0.01986 (8)
Cl10.42757 (8)0.74327 (6)0.30310 (4)0.02521 (12)
O10.7987 (2)0.61537 (17)0.40339 (13)0.0275 (3)
O20.8805 (2)0.79922 (17)0.19426 (14)0.0272 (3)
N10.7637 (2)0.56785 (19)0.08940 (15)0.0197 (3)
N20.6667 (2)0.41013 (19)0.29186 (15)0.0201 (3)
C10.8971 (4)0.6884 (3)0.5587 (2)0.0391 (6)
H1A0.79580.62940.60870.059*
H1B0.89540.78300.59420.059*
H1C1.01680.63350.55140.059*
C20.8716 (3)0.7181 (3)0.4385 (2)0.0261 (5)
C30.9315 (3)0.8491 (3)0.3737 (2)0.0313 (5)
H30.96910.92330.41260.038*
C40.9407 (3)0.8800 (2)0.2562 (2)0.0256 (5)
C51.0312 (4)1.0189 (3)0.1944 (2)0.0370 (6)
H5A1.03621.02250.11130.056*
H5B1.15801.01850.20050.056*
H5C0.95841.10630.23140.056*
C60.8170 (3)0.6495 (2)−0.01113 (19)0.0243 (4)
H60.85740.7464−0.01010.029*
C70.8159 (3)0.5982 (3)−0.11824 (19)0.0270 (5)
H70.85610.6597−0.18840.032*
C80.7568 (3)0.4593 (3)−0.12245 (18)0.0247 (4)
H80.75510.4239−0.19500.030*
C90.6982 (3)0.3695 (2)−0.01631 (18)0.0213 (4)
C100.6357 (3)0.2224 (2)−0.00981 (19)0.0254 (4)
H100.62790.1814−0.07900.030*
C110.5872 (3)0.1408 (2)0.0943 (2)0.0263 (5)
H110.54760.04300.09660.032*
C120.5948 (3)0.1995 (2)0.20076 (18)0.0216 (4)
C130.5500 (3)0.1196 (2)0.3117 (2)0.0266 (5)
H130.51000.02100.31980.032*
C140.5653 (3)0.1866 (2)0.40724 (19)0.0267 (5)
H140.53710.13410.48200.032*
C150.6226 (3)0.3326 (2)0.39506 (18)0.0230 (4)
H150.63020.37780.46260.028*
C160.6529 (3)0.3440 (2)0.19648 (17)0.0183 (4)
C170.7057 (3)0.4300 (2)0.08651 (17)0.0183 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.02849 (15)0.01578 (13)0.01782 (13)−0.00745 (10)−0.00941 (10)−0.00008 (9)
Cl10.0299 (3)0.0241 (3)0.0245 (2)−0.0016 (2)−0.0116 (2)−0.00471 (19)
O10.0404 (9)0.0230 (8)0.0251 (8)−0.0066 (7)−0.0179 (7)−0.0008 (6)
O20.0357 (9)0.0206 (8)0.0261 (8)−0.0129 (7)−0.0080 (7)−0.0005 (6)
N10.0240 (9)0.0180 (8)0.0181 (8)−0.0041 (7)−0.0076 (7)0.0001 (6)
N20.0254 (9)0.0168 (8)0.0189 (8)−0.0031 (7)−0.0075 (7)−0.0007 (6)
C10.0551 (17)0.0374 (14)0.0368 (13)0.0050 (12)−0.0312 (13)−0.0112 (11)
C20.0282 (11)0.0258 (11)0.0291 (11)0.0042 (9)−0.0149 (9)−0.0102 (9)
C30.0356 (13)0.0265 (12)0.0385 (13)−0.0064 (10)−0.0179 (11)−0.0102 (10)
C40.0211 (10)0.0200 (10)0.0355 (12)−0.0043 (8)−0.0060 (9)−0.0071 (9)
C50.0362 (13)0.0262 (12)0.0447 (14)−0.0134 (10)−0.0020 (11)−0.0083 (10)
C60.0290 (11)0.0211 (10)0.0238 (10)−0.0082 (8)−0.0092 (9)0.0032 (8)
C70.0327 (12)0.0289 (12)0.0200 (10)−0.0064 (9)−0.0093 (9)0.0051 (8)
C80.0282 (11)0.0293 (12)0.0183 (9)−0.0032 (9)−0.0088 (8)−0.0022 (8)
C90.0209 (10)0.0231 (10)0.0210 (10)−0.0020 (8)−0.0073 (8)−0.0018 (8)
C100.0308 (11)0.0237 (11)0.0246 (10)−0.0040 (9)−0.0105 (9)−0.0073 (8)
C110.0335 (12)0.0188 (10)0.0291 (11)−0.0075 (9)−0.0110 (9)−0.0046 (8)
C120.0237 (10)0.0187 (10)0.0221 (10)−0.0032 (8)−0.0059 (8)−0.0016 (8)
C130.0327 (12)0.0179 (10)0.0280 (11)−0.0058 (9)−0.0071 (9)0.0017 (8)
C140.0350 (12)0.0213 (11)0.0230 (10)−0.0057 (9)−0.0078 (9)0.0049 (8)
C150.0289 (11)0.0218 (10)0.0185 (9)−0.0042 (8)−0.0070 (8)0.0004 (8)
C160.0190 (9)0.0163 (9)0.0196 (9)−0.0013 (7)−0.0058 (7)−0.0011 (7)
C170.0184 (9)0.0177 (9)0.0195 (9)−0.0022 (7)−0.0065 (7)−0.0010 (7)

Geometric parameters (Å, °)

Cu1—Cl12.4717 (6)C5—H5C0.9800
Cu1—O11.927 (2)C6—C71.396 (3)
Cu1—O21.936 (2)C6—H60.9500
Cu1—N12.038 (2)C7—C81.372 (3)
Cu1—N22.025 (2)C7—H70.9500
O1—C21.271 (3)C8—C91.420 (3)
O2—C41.273 (3)C8—H80.9500
N1—C61.328 (3)C9—C171.399 (3)
N1—C171.357 (3)C9—C101.433 (3)
N2—C151.332 (3)C10—C111.359 (3)
N2—C161.360 (3)C10—H100.9500
C1—C21.507 (3)C11—C121.431 (3)
C1—H1A0.9800C11—H110.9500
C1—H1B0.9800C12—C161.401 (3)
C1—H1C0.9800C12—C131.418 (3)
C2—C31.390 (3)C13—C141.370 (3)
C3—C41.391 (3)C13—H130.9500
C3—H30.9500C14—C151.402 (3)
C4—C51.506 (3)C14—H140.9500
C5—H5A0.9800C15—H150.9500
C5—H5B0.9800C16—C171.435 (3)
O1—Cu1—O293.82 (7)H5B—C5—H5C109.5
O1—Cu1—N288.87 (7)N1—C6—C7122.4 (2)
O2—Cu1—N2164.40 (7)N1—C6—H6118.8
O1—Cu1—N1158.42 (7)C7—C6—H6118.8
O2—Cu1—N191.13 (7)C8—C7—C6120.18 (19)
N1—Cu1—N281.04 (7)C8—C7—H7119.9
O1—Cu1—Cl1102.88 (5)C6—C7—H7119.9
O2—Cu1—Cl197.34 (5)C7—C8—C9118.7 (2)
N2—Cu1—Cl197.03 (5)C7—C8—H8120.6
N1—Cu1—Cl197.28 (5)C9—C8—H8120.6
C2—O1—Cu1124.95 (14)C17—C9—C10119.20 (19)
C4—O2—Cu1124.08 (15)C17—C9—C8116.96 (19)
C6—N1—C17118.08 (18)C10—C9—C8123.8 (2)
C6—N1—Cu1129.04 (15)C11—C10—C9120.7 (2)
C17—N1—Cu1112.82 (13)C11—C10—H10119.7
C15—N2—C16117.97 (18)C9—C10—H10119.7
C15—N2—Cu1128.74 (15)C10—C11—C12121.3 (2)
C16—N2—Cu1113.24 (13)C10—C11—H11119.4
C2—C1—H1A109.5C12—C11—H11119.4
C2—C1—H1B109.5C16—C12—C13116.90 (19)
H1A—C1—H1B109.5C16—C12—C11118.84 (19)
C2—C1—H1C109.5C13—C12—C11124.2 (2)
H1A—C1—H1C109.5C14—C13—C12119.0 (2)
H1B—C1—H1C109.5C14—C13—H13120.5
O1—C2—C3125.0 (2)C12—C13—H13120.5
O1—C2—C1115.3 (2)C13—C14—C15120.21 (19)
C3—C2—C1119.7 (2)C13—C14—H14119.9
C2—C3—C4125.1 (2)C15—C14—H14119.9
C2—C3—H3117.4N2—C15—C14122.2 (2)
C4—C3—H3117.4N2—C15—H15118.9
O2—C4—C3125.5 (2)C14—C15—H15118.9
O2—C4—C5116.0 (2)N2—C16—C12123.74 (18)
C3—C4—C5118.4 (2)N2—C16—C17116.22 (18)
C4—C5—H5A109.5C12—C16—C17120.03 (19)
C4—C5—H5B109.5N1—C17—C9123.64 (18)
H5A—C5—H5B109.5N1—C17—C16116.42 (18)
C4—C5—H5C109.5C9—C17—C16119.93 (18)
H5A—C5—H5C109.5
O2—Cu1—O1—C210.33 (19)C6—C7—C8—C9−0.3 (3)
N2—Cu1—O1—C2174.95 (19)C7—C8—C9—C17−0.2 (3)
N1—Cu1—O1—C2113.2 (2)C7—C8—C9—C10−179.3 (2)
Cl1—Cu1—O1—C2−88.10 (18)C17—C9—C10—C11−1.2 (3)
O1—Cu1—O2—C4−11.32 (19)C8—C9—C10—C11177.9 (2)
N2—Cu1—O2—C4−110.9 (3)C9—C10—C11—C120.8 (4)
N1—Cu1—O2—C4−170.31 (18)C10—C11—C12—C160.2 (3)
Cl1—Cu1—O2—C492.21 (18)C10—C11—C12—C13−178.6 (2)
O1—Cu1—N1—C6−115.3 (2)C16—C12—C13—C140.1 (3)
O2—Cu1—N1—C6−12.0 (2)C11—C12—C13—C14178.9 (2)
N2—Cu1—N1—C6−178.4 (2)C12—C13—C14—C150.7 (3)
Cl1—Cu1—N1—C685.57 (19)C16—N2—C15—C140.7 (3)
O1—Cu1—N1—C1767.4 (2)Cu1—N2—C15—C14177.97 (16)
O2—Cu1—N1—C17170.77 (15)C13—C14—C15—N2−1.1 (4)
N2—Cu1—N1—C174.33 (14)C15—N2—C16—C120.1 (3)
Cl1—Cu1—N1—C17−91.68 (14)Cu1—N2—C16—C12−177.56 (16)
O1—Cu1—N2—C1517.41 (19)C15—N2—C16—C17−178.63 (19)
O2—Cu1—N2—C15117.6 (3)Cu1—N2—C16—C173.7 (2)
N1—Cu1—N2—C15178.3 (2)C13—C12—C16—N2−0.5 (3)
Cl1—Cu1—N2—C15−85.43 (19)C11—C12—C16—N2−179.4 (2)
O1—Cu1—N2—C16−165.19 (15)C13—C12—C16—C17178.19 (19)
O2—Cu1—N2—C16−65.0 (3)C11—C12—C16—C17−0.7 (3)
N1—Cu1—N2—C16−4.33 (14)C6—N1—C17—C9−0.3 (3)
Cl1—Cu1—N2—C1691.97 (14)Cu1—N1—C17—C9177.29 (16)
Cu1—O1—C2—C3−3.0 (3)C6—N1—C17—C16178.75 (19)
Cu1—O1—C2—C1178.82 (16)Cu1—N1—C17—C16−3.7 (2)
O1—C2—C3—C4−7.9 (4)C10—C9—C17—N1179.7 (2)
C1—C2—C3—C4170.2 (2)C8—C9—C17—N10.5 (3)
Cu1—O2—C4—C35.2 (3)C10—C9—C17—C160.7 (3)
Cu1—O2—C4—C5−175.75 (16)C8—C9—C17—C16−178.49 (19)
C2—C3—C4—O26.6 (4)N2—C16—C17—N10.0 (3)
C2—C3—C4—C5−172.4 (2)C12—C16—C17—N1−178.79 (19)
C17—N1—C6—C7−0.3 (3)N2—C16—C17—C9179.10 (19)
Cu1—N1—C6—C7−177.38 (17)C12—C16—C17—C90.3 (3)
N1—C6—C7—C80.6 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2552).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kwik, W. L. & Ang, H. G. (1978). Aust. J. Chem.31, 459–463.
  • Onawumi, O. O. E., Faboya, O. O. P., Odunola, O. A., Prasad, T. K. & Rajasekharan, M. V. (2008). Polyhedron, 27, 113–117.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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