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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m141.
Published online 2010 January 13. doi:  10.1107/S1600536809055640
PMCID: PMC2979737

Bis(2,2′-bipyrid­yl)(dichloro­acetato)copper(II) dichloro­acetate dihydrate

Abstract

In the title compound, [Cu(C2HCl2O2)(C10H8N2)2](C2HCl2O2)·2H2O, the CuII ion is bonded to two N,N′-bidentate 2,2′-bipyridyl ligands and one O-monodentate 2,2-dichloro­acetate anion in a distorted CuON4 trigonal-bipyramidal geometry, with the O atom occupying an equatorial site. In the crystal, the components are linked by O—H(...)O and O—H(...)Cl hydrogen bonds.

Related literature

For a related structure, see: Barszcz et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m141-scheme1.jpg

Experimental

Crystal data

  • [Cu(C2HCl2O2)(C10H8N2)2](C2HCl2O2)·2H2O
  • M r = 667.80
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m141-efi1.jpg
  • a = 9.9710 (7) Å
  • b = 11.7307 (9) Å
  • c = 12.4736 (9) Å
  • α = 105.407 (1)°
  • β = 101.499 (1)°
  • γ = 95.513 (1)°
  • V = 1361.07 (17) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.24 mm−1
  • T = 293 K
  • 0.22 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 7789 measured reflections
  • 5280 independent reflections
  • 4592 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.097
  • S = 1.06
  • 5280 reflections
  • 365 parameters
  • 7 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.65 e Å−3
  • Δρmin = −0.64 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055640/hb5295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055640/hb5295Isup2.hkl

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

Acknowledgments

The authors would like to thank the Science Foundation of Weifang University (No. 2009Z24) and the Natural Science Foundation of Shandong Province (No. ZR2009BM041)

supplementary crystallographic information

Experimental

Copper(II) 2,2-dicholoracetate, 0.32 g (1 mmol) and 2,2'-bipyridine 0.31 g (2 mmol) were added to 65 ml anhydrous alcohol under stirring. The mixture was refluxed for 7 h. The blue solution was filtered and the filtrate was left to stand undisturbed. Upon slow evaporation at room temperature, blue blocks of (I) appeared three days later and were separated by filtration.

Refinement

The water H atoms were located in a difference map and freely refined. The C-bonded H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure for (I), with displacement ellipsoids drawn at the 30% probability level.

Crystal data

[Cu(C2HCl2O2)(C10H8N2)2](C2HCl2O2)·2H2OZ = 2
Mr = 667.80F(000) = 678
Triclinic, P1Dx = 1.629 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.9710 (7) ÅCell parameters from 2240 reflections
b = 11.7307 (9) Åθ = 2.2–28.3°
c = 12.4736 (9) ŵ = 1.24 mm1
α = 105.407 (1)°T = 293 K
β = 101.499 (1)°Block, blue
γ = 95.513 (1)°0.22 × 0.20 × 0.18 mm
V = 1361.07 (17) Å3

Data collection

Bruker SMART CCD diffractometer4592 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
graphiteθmax = 26.0°, θmin = 1.8°
phi and ω scansh = −11→12
7789 measured reflectionsk = −13→14
5280 independent reflectionsl = −15→14

Refinement

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) = 0.097w = 1/[σ2(Fo2) + (0.0542P)2 + 0.3598P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
5280 reflectionsΔρmax = 0.65 e Å3
365 parametersΔρmin = −0.64 e Å3
7 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0256 (15)

Special details

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)

xyzUiso*/Ueq
Cu10.02070 (3)0.28505 (2)0.24318 (2)0.03074 (11)
Cl10.45242 (8)0.39464 (9)0.06435 (8)0.0741 (3)
Cl20.50350 (6)0.30032 (6)0.25678 (6)0.04867 (17)
O10.21727 (16)0.36582 (14)0.27220 (14)0.0396 (4)
O20.17501 (17)0.31459 (16)0.08196 (15)0.0459 (4)
N1−0.06224 (19)0.43199 (16)0.24029 (15)0.0318 (4)
N2−0.05985 (19)0.31277 (16)0.39146 (15)0.0326 (4)
N3−0.13923 (19)0.17107 (16)0.11654 (15)0.0328 (4)
N40.08416 (19)0.12907 (17)0.24147 (16)0.0347 (4)
C1−0.0573 (3)0.4885 (2)0.1606 (2)0.0406 (5)
H1−0.00070.46590.11030.049*
C2−0.1329 (3)0.5790 (2)0.1503 (2)0.0465 (6)
H2−0.12800.61620.09360.056*
C3−0.2157 (3)0.6134 (2)0.2255 (2)0.0467 (6)
H3−0.26910.67320.21930.056*
C4−0.2185 (2)0.5581 (2)0.3104 (2)0.0415 (5)
H4−0.27220.58160.36290.050*
C5−0.1403 (2)0.46721 (18)0.31641 (18)0.0303 (4)
C6−0.1365 (2)0.40123 (18)0.40308 (17)0.0299 (4)
C7−0.2055 (2)0.4282 (2)0.4908 (2)0.0404 (5)
H6−0.25720.49050.49820.049*
C8−0.1960 (3)0.3608 (2)0.5670 (2)0.0460 (6)
H8−0.24150.37710.62630.055*
C9−0.1187 (3)0.2699 (2)0.5541 (2)0.0472 (6)
H9−0.11140.22330.60410.057*
C10−0.0515 (3)0.2483 (2)0.4653 (2)0.0411 (5)
H100.00130.18680.45690.049*
C11−0.2514 (2)0.1998 (2)0.0568 (2)0.0405 (5)
H11−0.26050.28020.07020.049*
C12−0.3538 (3)0.1155 (3)−0.0237 (2)0.0495 (6)
H12−0.43000.1383−0.06440.059*
C13−0.3404 (3)−0.0027 (3)−0.0422 (2)0.0525 (7)
H13−0.4082−0.0614−0.09600.063*
C14−0.2268 (3)−0.0348 (2)0.0188 (2)0.0457 (6)
H14−0.2175−0.11500.00720.055*
C15−0.1260 (2)0.05451 (19)0.09785 (18)0.0334 (5)
C160.0007 (2)0.0309 (2)0.16703 (19)0.0351 (5)
C170.0356 (3)−0.0829 (2)0.1571 (2)0.0478 (6)
H17−0.0222−0.15000.10510.057*
C180.1576 (3)−0.0946 (3)0.2256 (3)0.0571 (8)
H180.1831−0.16980.21990.069*
C190.2412 (3)0.0060 (3)0.3024 (2)0.0528 (7)
H190.3232−0.00050.34950.063*
C200.2015 (3)0.1165 (2)0.3086 (2)0.0450 (6)
H200.25770.18430.36070.054*
C210.2517 (2)0.35388 (19)0.1777 (2)0.0341 (5)
C220.4076 (2)0.3961 (2)0.1938 (2)0.0402 (5)
H220.43240.47780.24560.048*
Cl30.17481 (9)0.06640 (8)0.59492 (10)0.0833 (3)
Cl40.36379 (9)−0.04850 (8)0.72163 (7)0.0722 (2)
O30.4801 (3)0.2075 (2)0.7501 (2)0.0807 (7)
O40.4943 (3)0.1598 (2)0.5687 (3)0.0971 (9)
C230.3436 (3)0.0293 (2)0.6185 (2)0.0466 (6)
H23A0.3545−0.02400.54660.056*
C240.4501 (3)0.1442 (3)0.6506 (3)0.0550 (7)
O1W0.4574 (3)0.3842 (2)0.5424 (2)0.0744 (7)
H1A0.455 (4)0.384 (4)0.4747 (19)0.089*
H1B0.467 (4)0.312 (2)0.543 (3)0.089*
O2W0.2759 (3)0.6333 (2)0.1579 (3)0.0885 (8)
H2A0.299 (3)0.579 (2)0.104 (2)0.106*
H2B0.349 (3)0.686 (3)0.192 (3)0.106*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.03054 (16)0.02735 (16)0.03555 (17)0.00635 (10)0.00873 (11)0.00987 (11)
Cl10.0572 (4)0.1167 (7)0.0791 (5)0.0245 (5)0.0366 (4)0.0615 (5)
Cl20.0370 (3)0.0532 (4)0.0565 (4)0.0097 (3)0.0046 (3)0.0210 (3)
O10.0362 (8)0.0390 (9)0.0408 (9)0.0010 (7)0.0126 (7)0.0062 (7)
O20.0399 (9)0.0490 (10)0.0437 (10)0.0044 (8)0.0057 (8)0.0091 (8)
N10.0333 (9)0.0273 (9)0.0355 (9)0.0062 (7)0.0103 (8)0.0083 (7)
N20.0341 (9)0.0306 (9)0.0314 (9)0.0031 (7)0.0070 (8)0.0073 (7)
N30.0332 (9)0.0300 (9)0.0337 (9)0.0034 (7)0.0085 (8)0.0070 (7)
N40.0354 (10)0.0352 (10)0.0375 (10)0.0100 (8)0.0118 (8)0.0130 (8)
C10.0478 (14)0.0352 (12)0.0423 (13)0.0085 (10)0.0143 (11)0.0140 (10)
C20.0562 (16)0.0365 (13)0.0501 (14)0.0084 (11)0.0097 (12)0.0199 (11)
C30.0469 (14)0.0349 (13)0.0582 (16)0.0147 (11)0.0073 (12)0.0140 (11)
C40.0384 (12)0.0368 (13)0.0480 (14)0.0108 (10)0.0112 (11)0.0076 (10)
C50.0250 (10)0.0268 (10)0.0339 (11)−0.0008 (8)0.0038 (8)0.0040 (8)
C60.0251 (10)0.0287 (10)0.0300 (10)−0.0027 (8)0.0036 (8)0.0031 (8)
C70.0343 (12)0.0429 (13)0.0396 (12)0.0027 (10)0.0116 (10)0.0034 (10)
C80.0433 (14)0.0579 (16)0.0347 (12)−0.0009 (12)0.0162 (11)0.0078 (11)
C90.0540 (15)0.0526 (15)0.0374 (13)−0.0002 (12)0.0121 (11)0.0191 (11)
C100.0464 (14)0.0402 (13)0.0401 (13)0.0074 (10)0.0115 (11)0.0160 (10)
C110.0361 (12)0.0399 (13)0.0423 (13)0.0057 (10)0.0047 (10)0.0100 (10)
C120.0372 (13)0.0603 (17)0.0445 (14)0.0023 (12)0.0023 (11)0.0119 (12)
C130.0465 (15)0.0520 (16)0.0445 (14)−0.0091 (12)0.0039 (12)0.0008 (12)
C140.0526 (15)0.0332 (12)0.0450 (14)−0.0018 (11)0.0142 (12)0.0018 (10)
C150.0377 (12)0.0306 (11)0.0328 (11)0.0034 (9)0.0149 (9)0.0068 (9)
C160.0426 (12)0.0314 (11)0.0382 (12)0.0084 (10)0.0209 (10)0.0123 (9)
C170.0645 (17)0.0339 (13)0.0553 (15)0.0157 (12)0.0273 (13)0.0179 (11)
C180.081 (2)0.0492 (16)0.0656 (18)0.0368 (15)0.0391 (17)0.0323 (14)
C190.0521 (16)0.0683 (19)0.0564 (16)0.0319 (14)0.0212 (13)0.0349 (15)
C200.0412 (13)0.0545 (15)0.0449 (13)0.0157 (12)0.0108 (11)0.0207 (12)
C210.0345 (11)0.0244 (10)0.0450 (13)0.0052 (9)0.0116 (10)0.0110 (9)
C220.0361 (12)0.0368 (12)0.0500 (14)0.0044 (10)0.0134 (11)0.0148 (11)
Cl30.0527 (4)0.0712 (5)0.1169 (8)0.0183 (4)−0.0088 (5)0.0304 (5)
Cl40.0675 (5)0.0819 (6)0.0722 (5)0.0014 (4)−0.0030 (4)0.0485 (4)
O30.0808 (17)0.0708 (16)0.0752 (16)−0.0105 (13)0.0049 (13)0.0133 (13)
O40.139 (3)0.0615 (15)0.108 (2)0.0046 (15)0.068 (2)0.0287 (14)
C230.0518 (15)0.0491 (15)0.0428 (13)0.0156 (12)0.0092 (12)0.0187 (11)
C240.0577 (17)0.0466 (16)0.0661 (19)0.0142 (13)0.0198 (15)0.0196 (14)
O1W0.0842 (16)0.0731 (16)0.0853 (17)0.0306 (13)0.0462 (15)0.0298 (14)
O2W0.0756 (17)0.0565 (15)0.130 (2)0.0066 (12)0.0219 (17)0.0243 (15)

Geometric parameters (Å, °)

Cu1—N11.9879 (18)C9—H90.9300
Cu1—N41.9889 (18)C10—H100.9300
Cu1—O12.0121 (16)C11—C121.378 (3)
Cu1—N32.0711 (18)C11—H110.9300
Cu1—N22.1201 (18)C12—C131.368 (4)
Cl1—C221.755 (3)C12—H120.9300
Cl2—C221.780 (2)C13—C141.377 (4)
O1—C211.268 (3)C13—H130.9300
O2—C211.225 (3)C14—C151.390 (3)
N1—C11.340 (3)C14—H140.9300
N1—C51.352 (3)C15—C161.476 (3)
N2—C101.333 (3)C16—C171.391 (3)
N2—C61.341 (3)C17—C181.382 (4)
N3—C111.339 (3)C17—H170.9300
N3—C151.349 (3)C18—C191.377 (4)
N4—C201.341 (3)C18—H180.9300
N4—C161.350 (3)C19—C201.379 (4)
C1—C21.378 (3)C19—H190.9300
C1—H10.9300C20—H200.9300
C2—C31.377 (4)C21—C221.542 (3)
C2—H20.9300C22—H220.9800
C3—C41.385 (4)Cl3—C231.766 (3)
C3—H30.9300Cl4—C231.757 (3)
C4—C51.388 (3)O3—C241.225 (4)
C4—H40.9300O4—C241.239 (4)
C5—C61.484 (3)C23—C241.540 (4)
C6—C71.388 (3)C23—H23A0.9800
C7—C81.384 (4)O1W—H1A0.839 (18)
C7—H60.9300O1W—H1B0.861 (19)
C8—C91.369 (4)O2W—H2A0.884 (16)
C8—H80.9300O2W—H2B0.867 (18)
C9—C101.385 (3)
N1—Cu1—N4174.19 (8)C9—C10—H10118.8
N1—Cu1—O194.77 (7)N3—C11—C12122.9 (2)
N4—Cu1—O191.01 (7)N3—C11—H11118.5
N1—Cu1—N394.63 (7)C12—C11—H11118.5
N4—Cu1—N380.37 (7)C13—C12—C11118.3 (3)
O1—Cu1—N3142.56 (7)C13—C12—H12120.9
N1—Cu1—N279.44 (7)C11—C12—H12120.9
N4—Cu1—N298.73 (7)C12—C13—C14120.0 (2)
O1—Cu1—N2114.17 (7)C12—C13—H13120.0
N3—Cu1—N2103.17 (7)C14—C13—H13120.0
C21—O1—Cu1109.56 (14)C13—C14—C15119.0 (2)
C1—N1—C5119.18 (19)C13—C14—H14120.5
C1—N1—Cu1123.79 (15)C15—C14—H14120.5
C5—N1—Cu1116.62 (15)N3—C15—C14121.1 (2)
C10—N2—C6118.93 (19)N3—C15—C16115.17 (19)
C10—N2—Cu1127.95 (16)C14—C15—C16123.8 (2)
C6—N2—Cu1112.90 (14)N4—C16—C17121.1 (2)
C11—N3—C15118.69 (19)N4—C16—C15115.04 (19)
C11—N3—Cu1127.97 (16)C17—C16—C15123.8 (2)
C15—N3—Cu1113.30 (14)C18—C17—C16119.0 (3)
C20—N4—C16119.4 (2)C18—C17—H17120.5
C20—N4—Cu1124.53 (17)C16—C17—H17120.5
C16—N4—Cu1116.08 (15)C19—C18—C17119.5 (2)
N1—C1—C2122.5 (2)C19—C18—H18120.3
N1—C1—H1118.7C17—C18—H18120.3
C2—C1—H1118.7C18—C19—C20119.1 (3)
C3—C2—C1118.8 (2)C18—C19—H19120.5
C3—C2—H2120.6C20—C19—H19120.5
C1—C2—H2120.6N4—C20—C19121.9 (3)
C2—C3—C4119.2 (2)N4—C20—H20119.0
C2—C3—H3120.4C19—C20—H20119.0
C4—C3—H3120.4O2—C21—O1126.7 (2)
C3—C4—C5119.4 (2)O2—C21—C22120.8 (2)
C3—C4—H4120.3O1—C21—C22112.5 (2)
C5—C4—H4120.3C21—C22—Cl1112.61 (17)
N1—C5—C4120.8 (2)C21—C22—Cl2108.80 (16)
N1—C5—C6115.24 (18)Cl1—C22—Cl2108.94 (13)
C4—C5—C6123.9 (2)C21—C22—H22108.8
N2—C6—C7121.7 (2)Cl1—C22—H22108.8
N2—C6—C5114.97 (18)Cl2—C22—H22108.8
C7—C6—C5123.4 (2)C24—C23—Cl4113.67 (19)
C8—C7—C6118.9 (2)C24—C23—Cl3109.08 (18)
C8—C7—H6120.6Cl4—C23—Cl3109.69 (15)
C6—C7—H6120.6C24—C23—H23A108.1
C9—C8—C7119.2 (2)Cl4—C23—H23A108.1
C9—C8—H8120.4Cl3—C23—H23A108.1
C7—C8—H8120.4O3—C24—O4128.5 (3)
C8—C9—C10119.0 (2)O3—C24—C23118.1 (3)
C8—C9—H9120.5O4—C24—C23113.4 (3)
C10—C9—H9120.5H1A—O1W—H1B104 (4)
N2—C10—C9122.3 (2)H2A—O2W—H2B107 (2)
N2—C10—H10118.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1A···Cl20.84 (2)2.79 (2)3.571 (3)155 (4)
O1W—H1B···O40.86 (2)1.93 (2)2.787 (4)171 (4)
O2W—H2A···Cl10.88 (2)2.76 (2)3.511 (3)144 (3)
O2W—H2B···O3i0.87 (2)1.89 (2)2.757 (3)172 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5295).

References

  • Barszcz, B., Glowiak, T., Jezierska, J. & Tomkiewicz, A. (2004). Polyhedron, 23, 1308–1316
  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography