The reaction of CuCl2 with 1,6-diphenyl-1,3,5,6-hexanetetrone and 2,2′-bipyridine (bipy) in ethanol gave crystals of the corresponding bimetallic complex, [Cu2(C18H12O4)Cl2(C10H8N2)2]·2H2O. The molecule is centrosymmetric with each CuII ion coordinated to two oxygen atoms from the tetronediate, two nitrogen atoms from a bipy ligand and one coordinated chloride ion. A water molecule of crystallization forms hydrogen bonds to the chloride ions, linking the molecules into a chain parallel to the bc-face diagonal. © 2023 The Author(s)

Nye, Luke

Tefler, Shane G.

Turnbull, Mark M

English

Clark University

Clark University Clark Digital Commons Chemistry Faculty Works by Department and/or School 8-30-2023 μ-1,6-Dioxo-1,6-diphenylhexane-3,4-diolato-bis[(2,2′-bipyridine)chloridocopper(II)] dihydrate a; b; a Luke Nye Shane G. Tefler Mark M. Turnbull Follow this and additional works at: https://commons.clarku.edu/chemistry  Part of the Chemistry Commons data reportsIUCrData (2023). 8, x230713 https://doi.org/10.1107/S2414314623007137 1 of 3ISSN 2414-3146Received 10 August 2023Accepted 12 August 2023Edited by E. R. T. Tiekink, Sunway University,Malaysia‡ Present address: Waters Corp. 34 Maple St,Milford, MA 01757, USA.Keywords: CuII; hydrate; hydrogen-bonding;tetronedioate; crystal structure.CCDC reference: 2288356Structural data: full structural data are availablefrom iucrdata.iucr.orgPublished under a CC BY 4.0 licencel-1,6-Dioxo-1,6-diphenylhexane-3,4-diolato-bis[(2,20-bipyridine)chloridocopper(II)] dihydrateLuke Nye,a‡ Shane G. Telferb and Mark M. Turnbulla*aCarlson School of Chemistry and Biochemistry, Clark University, 950 Main St., Worcester, MA 01610, USA, and bSchoolof Natural Sciences, Institute of Fundamental Sciences, Massey University, Palmerston North, New Zealand. *Corre-spondence e-mail: mturnbull@clarku.eduThe reaction of CuCl2 with 1,6-diphenyl-1,3,5,6-hexanetetrone and 2,20-bi-pyridine (bipy) in ethanol gave crystals of the corresponding bimetallic complex,[Cu2(C18H12O4)Cl2(C10H8N2)2]·2H2O. The molecule is centrosymmetric witheach CuII ion coordinated to two oxygen atoms from the tetronediate, twonitrogen atoms from a bipy ligand and one coordinated chloride ion. A watermolecule of crystallization forms hydrogen bonds to the chloride ions, linkingthe molecules into a chain parallel to the bc-face diagonal.Structure description1,6-Diphenyl-1,3,4,6-hexanetetrone has been known for over 100 years (Widman &Virgin, 1909) and its structure has been reported (Kaitner et al., 1992). Both its synthesisby oxidation (Balenović et al., 1954) and its reactions with oxidizing agents have beenstudied (Balenović, 1948; Bird & Thorley, 1977; Poje et al., 1978), as well as its use as astarting material for the preparation of a variety of aminated products (Lacan et al., 1973;Unterhalt & Pindur, 1977; Kaitner et al., 1992; Waring et al., 2002; Kobelev et al., 2019).The backbone core resembles a bis-acac structure and and as such it has been used in thepreparation of transition-metal complexes (Boucher & Bailar, 1964; Saalfrank et al., 1998;Nawar, 1994). However, we were surprised to find that there are no reported structures oftransition-metal complexes containing this ligand (Groom et al., 2016). We investigatedits coordination chemistry with CuII as part of our studies on potential magnetic ladders(Monroe et al., 2022).The molecule sits astride a crystallographic inversion center (Fig. 1). Each CuII ion isfive-coordinate, including two oxygen atoms from the tetronediate ligand, two nitrogenatoms from a bipy molecule and one coordinated chloride ion. The CuN2O2 equatorialplane is nearly planar (mean deviation of the N2O2 donor set = 0.0219 Å) with the CuIIion displaced [0.2219 (15) Å] toward the chloride ion. The 1,3-dionato motif chelates acopper ion and generates a six-membered metallocyclic ringthat is only slightly less planar (mean deviation of constituentatoms = 0.1207 Å). The two heterocyclic rings are co-planar asrequired by symmetry. The pyridyl rings are canted 0.67 (13)�from each other.�-Stacking is observed between molecules. The Cu1-dionato ring sits above the N11-containing bpy ring with aninterplanar distance of 3.33 (2) Å; the rings are canted 4.4 (2)�with respect to each other. The distance between the ringcentroids is 3.73 (2) Å with a slip angle of 25.1 (3)�. Thiseffectively blocks the vacant coordination site on Cu1,preventing the addition of a sixth ligand. �-Stacking is alsoobserved between the phenyl rings of the tetrone ligand.Adjacent phenyl rings are parallel with an interplanar distanceof 3.33 (2) Å with a slip angle of 22.8 (3)�. The bimetallic unitsare linked into chains via hydrogen bonds between the solventwater molecules and chloride ions (Table 1 and Fig. 2).Synthesis and crystallizationCuCl2 (0.403 g, 2.99 mmol) was dissolved in 50 ml of absoluteethanol to generate a green solution. 2,20-Bipyridine (0.469 g,3.01 mmol) was added to the solution with stirring to make alight-blue slurry. Addition of 1,6-diphenyl-1,3,4,6-hexane-tetrone (0.438 g, 1.49 mmol) generated a lime green slurry,which was stirred for 1 h. The precipitate was recovered byvacuum filtration, washed with ethanol and dried in air to yield0.973 g of lime green powder (77%). Crystals suitable forX-ray diffraction were grown by recrystallization from DMF.RefinementCrystal data, data collection and structure refinement detailsare summarized in Table 2. Eight reflections were omittedfrom the final refinement owing to poor agreement; details areincluded in the CIF.data reports2 of 3 Nye et al. � [Cu2(C18H12O4)Cl2(C10H8N2)2]·2H2O IUCrData (2023). 8, x230713Table 1Hydrogen-bond geometry (Å, �).D—H� � �A D—H H� � �A D� � �A D—H� � �AO2—H2A� � �Cl1 0.82 (5) 2.41 (5) 3.224 (3) 171 (5)O2—H2B� � �Cl1i 0.98 (4) 2.33 (5) 3.307 (4) 172 (4)Symmetry code: (i)   x;   y;   z þ 1.Figure 2Chain formation via hydrogen bonding. Symmetry operation B:   x,   y,1   z.Table 2Experimental details.Crystal dataChemical formula [Cu2(C18H12O4)Cl2(C10H8N2)2]·2H2OMr 838.65Crystal system, space group Triclinic, P1Temperature (K) 123a, b, c (Å) 8.7211 (2), 10.4194 (2), 10.5243 (7)�, �, � (�) 106.426 (7), 109.090 (8), 90.373 (6)V (Å3) 861.67 (8)Z 1Radiation type Cu K�� (mm  1) 3.41Crystal size (mm) 0.13 � 0.09 � 0.02Data collectionDiffractometer Rigaku SpiderAbsorption correction Multi-scan (ABSCOR; Rigaku,1995)Tmin, Tmax 0.641, 0.929No. of measured, independent andobserved [I > 2�(I)] reflections7470, 2552, 1901Rint 0.046�max (�) 61.1(sin �/�)max (Å  1) 0.568RefinementR[F 2 > 2�(F 2)], wR(F 2), S 0.047, 0.121, 1.13No. of reflections 2552No. of parameters 241H-atom treatment H atoms treated by a mixture ofindependent and constrainedrefinement��max, ��min (e Å  3) 0.57,   0.49Computer programs: CrystalClear (Rigaku, 2005), PROCESS-AUTO (Rigaku, 1998),SHELXS97 (Sheldrick, 2008), and SHELXL2018/3 (Sheldrick, 2015), XP (Sheldrick,2008).Figure 1The molecular structure of the title compound. Only the asymmetric unitand Cu coordination spheres are labeled. Hydrogen atoms are shown asspheres of arbitrary size. Symmetry operation B:   x, 1   y, 2   z.AcknowledgementsLN is grateful for a Murdock Summer Research Fellowship.Author contributions: LN (synthesis, characterization) JLW(X-ray data) MMT (concept, writing).Funding informationFunding for this research was provided by: National ScienceFoundation (grant No. IMR-0314773 to MMT).ReferencesBalenović, K. (1948). Recl Trav. Chim. Pays Bas, 67, 282–284.Balenović, K., Cerar, D. & Filipović, L. (1954). J. Org. Chem. 19,1556–1561.Bird, C. W. & Thorley, P. (1977). Chem. Ind. (London), 872.Boucher, L. J. & Bailar, J. C. Jr (1964). Inorg. Chem. 3, 589–593.Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). ActaCryst. B72, 171–179.Kaitner, B., Jovanovski, G. & Janev, I. (1992). Acta Cryst. C48, 127–129.Kobelev, A. I., Stepanova, E. E., Dmitriev, M. V. & Maslivets, A. N.(2019). Chem. Heterocycl. Cmpd, 55, 897–901.Lacan, M., Sehovic, Dj. & Kules, M. (1973). Croat. Chem. Acta, 45,555–560.Monroe, J. C., Carvajal, M. A., Landee, C. P., Deumal, M., Turnbull,M. M., Wikaira, J. L. & Dawe, L. N. (2022). Dalton Trans. 51, 4653–4667.Nawar, N. (1994). Mansoura Sci. Bull. A 21, 69-77.Poje, M., Gašpert, B. & Balenović, K. (1978). Recl Trav. Chim. PaysBas, 97, 242–244.Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo,Japan.Rigaku (2005). CrystalClear. Rigaku Americas Corporation, TheWoodlands, Texas, USA.Saalfrank, R. W., Löw, N., Demleitner, B., Stalke, D. & Teichert, M.(1998). Chem. Eur. J. 4, 1305–1311.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.Unterhalt, B. & Pindur, U. (1977). Arch. Pharm. Pharm. Med. Chem.310, 264–268.Waring, M. J., Ben-Hadda, T., Kotchevar, A. T., Ramdani, A.,Touzani, R., Elkadiri, S., Hakkou, A., Bouakka, M. & Ellis, T.(2002). Molecules, 7, 641–656.Widman, O. & Virgin, E. (1909). Ber. Dtsch. Chem. Ges. 42, 2794–2806.data reportsIUCrData (2023). 8, x230713 Nye et al. � [Cu2(C18H12O4)Cl2(C10H8N2)2]·2H2O 3 of 3data reportsdata-1IUCrData (2023). 8, x230713    full crystallographic dataIUCrData (2023). 8, x230713    [https://doi.org/10.1107/S2414314623007137]µ-1,6-Dioxo-1,6-diphenylhexane-3,4-diolato-bis[(2,2′-bipyridine)-chloridocopper(II)] dihydrateLuke Nye, Shane G. Telfer and Mark M. Turnbullµ-1,6-Dioxo-1,6-diphenylhexane-3,4-diolato-bis[(2,2′-bipyridine)chloridocopper(II)] dihydrate Crystal data [Cu2(C18H12O4)Cl2(C10H8N2)2]·2H2OMr = 838.65Triclinic, P1a = 8.7211 (2) Åb = 10.4194 (2) Åc = 10.5243 (7) Åα = 106.426 (7)°β = 109.090 (8)°γ = 90.373 (6)°V = 861.67 (8) Å3Z = 1F(000) = 428Dx = 1.616 Mg m−3Cu Kα radiation, λ = 1.54178 ÅCell parameters from 3450 reflectionsθ = 6.6–72.0°µ = 3.41 mm−1T = 123 KPlate, green0.13 × 0.09 × 0.02 mmData collection Rigaku Spider diffractometerRadiation source: rotating anodeConfocal optics monochromatorDetector resolution: 10 pixels mm-1ω–scansAbsorption correction: multi-scan (ABSCOR; Rigaku, 1995)Tmin = 0.641, Tmax = 0.9297470 measured reflections2552 independent reflections1901 reflections with I > 2σ(I)Rint = 0.046θmax = 61.1°, θmin = 6.6°h = −9→9k = −8→11l = −11→11Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.047wR(F2) = 0.121S = 1.132552 reflections241 parameters0 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: mixedH atoms treated by a mixture of independent and constrained refinementw = 1/[σ2(Fo2) + (0.0514P)2 + 0.1469P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.57 e Å−3Δρmin = −0.49 e Å−3data reportsdata-2IUCrData (2023). 8, x230713    Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.Refinement. Hydrogen atoms bonded to carbon atoms were placed geometrically and refined with fixed isotropic thermal parameters. Hydrogen atoms bonded to O2 were located in the difference map and their positions refined with fixed isotropic thermal parameters (O—H = 0.82 (5) & 0.98 (4) Å).Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/UeqCu1 0.33000 (7) 0.32164 (6) 0.96525 (6) 0.0307 (2)Cl1 0.11639 (12) 0.13154 (10) 0.77171 (10) 0.0345 (3)O1 0.1754 (3) 0.4177 (3) 1.0408 (3) 0.0324 (7)C1 0.0704 (5) 0.4796 (4) 0.9723 (4) 0.0254 (10)C2 0.0728 (5) 0.5143 (4) 0.8569 (4) 0.0294 (10)H2 −0.017613 0.555390 0.812000 0.035*O3 0.3211 (3) 0.4301 (3) 0.8421 (3) 0.0330 (7)C3 0.2001 (5) 0.4937 (4) 0.7987 (4) 0.0271 (10)C4 0.1975 (5) 0.5506 (4) 0.6837 (4) 0.0303 (10)C5 0.2992 (5) 0.5074 (4) 0.6059 (4) 0.0329 (11)H5 0.372026 0.443341 0.628745 0.039*C6 0.2963 (5) 0.5555 (5) 0.4963 (5) 0.0411 (12)H6 0.365425 0.523306 0.443454 0.049*C7 0.1939 (6) 0.6503 (5) 0.4627 (5) 0.0422 (12)H7 0.193055 0.683511 0.387222 0.051*C8 0.0922 (5) 0.6969 (4) 0.5389 (5) 0.0393 (12)H8 0.022438 0.763064 0.516788 0.047*C9 0.0926 (5) 0.6469 (4) 0.6470 (4) 0.0310 (10)H9 0.020939 0.677797 0.697730 0.037*N11 0.5341 (4) 0.2451 (3) 0.9445 (3) 0.0282 (8)C11 0.6014 (5) 0.2564 (4) 0.8501 (4) 0.0339 (11)H11 0.549680 0.303493 0.785150 0.041*C12 0.7425 (5) 0.2020 (4) 0.8441 (4) 0.0343 (11)H12 0.788780 0.212980 0.777127 0.041*C13 0.8170 (5) 0.1309 (4) 0.9368 (4) 0.0302 (10)H13 0.914522 0.092053 0.933922 0.036*C14 0.7475 (5) 0.1177 (4) 1.0326 (4) 0.0277 (10)H14 0.796296 0.069566 1.097313 0.033*C15 0.6054 (5) 0.1754 (4) 1.0339 (4) 0.0237 (9)C16 0.5227 (5) 0.1699 (4) 1.1351 (4) 0.0275 (10)C17 0.5733 (5) 0.1040 (4) 1.2364 (4) 0.0273 (10)H17 0.667767 0.057482 1.244906 0.033*C18 0.4850 (5) 0.1061 (4) 1.3261 (4) 0.0318 (11)H18 0.519826 0.063659 1.398103 0.038*C19 0.3447 (5) 0.1721 (4) 1.3075 (4) 0.0362 (11)H19 0.280783 0.173765 1.365635 0.043*data reportsdata-3IUCrData (2023). 8, x230713    C20 0.2994 (5) 0.2349 (4) 1.2041 (4) 0.0316 (11)H20 0.203908 0.280215 1.193139 0.038*N12 0.3846 (4) 0.2349 (3) 1.1175 (3) 0.0282 (8)O2 0.2128 (4) 0.0355 (4) 0.4911 (4) 0.0538 (10)H2A 0.178 (6) 0.059 (5) 0.557 (5) 0.065*H2B 0.110 (6) −0.013 (4) 0.420 (5) 0.065*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23Cu1 0.0320 (4) 0.0347 (4) 0.0347 (4) 0.0178 (3) 0.0164 (3) 0.0183 (3)Cl1 0.0317 (6) 0.0400 (7) 0.0367 (6) 0.0129 (5) 0.0136 (5) 0.0164 (5)O1 0.0366 (17) 0.0391 (18) 0.0347 (17) 0.0202 (14) 0.0200 (14) 0.0217 (14)C1 0.030 (2) 0.022 (2) 0.027 (2) 0.0052 (19) 0.012 (2) 0.0094 (19)C2 0.027 (2) 0.034 (3) 0.032 (2) 0.0130 (19) 0.011 (2) 0.016 (2)O3 0.0297 (16) 0.0351 (17) 0.0388 (17) 0.0198 (14) 0.0135 (13) 0.0156 (14)C3 0.031 (3) 0.024 (2) 0.026 (2) 0.0026 (19) 0.009 (2) 0.0098 (19)C4 0.025 (2) 0.032 (3) 0.030 (2) 0.0030 (19) 0.0050 (19) 0.009 (2)C5 0.029 (2) 0.039 (3) 0.038 (3) 0.011 (2) 0.014 (2) 0.021 (2)C6 0.039 (3) 0.050 (3) 0.042 (3) 0.004 (2) 0.018 (2) 0.021 (2)C7 0.052 (3) 0.046 (3) 0.036 (3) −0.005 (2) 0.013 (2) 0.025 (2)C8 0.036 (3) 0.035 (3) 0.048 (3) 0.008 (2) 0.008 (2) 0.020 (2)C9 0.031 (2) 0.038 (3) 0.030 (2) 0.008 (2) 0.010 (2) 0.020 (2)N11 0.027 (2) 0.032 (2) 0.031 (2) 0.0111 (16) 0.0163 (17) 0.0114 (17)C11 0.038 (3) 0.032 (3) 0.034 (3) 0.013 (2) 0.014 (2) 0.012 (2)C12 0.038 (3) 0.037 (3) 0.037 (3) 0.012 (2) 0.022 (2) 0.013 (2)C13 0.032 (2) 0.028 (2) 0.036 (3) 0.0114 (19) 0.015 (2) 0.013 (2)C14 0.034 (2) 0.028 (2) 0.027 (2) 0.0105 (19) 0.011 (2) 0.017 (2)C15 0.028 (2) 0.021 (2) 0.025 (2) 0.0064 (18) 0.0106 (19) 0.0097 (19)C16 0.024 (2) 0.027 (2) 0.034 (2) 0.0078 (18) 0.0102 (19) 0.013 (2)C17 0.034 (2) 0.024 (2) 0.034 (3) 0.0095 (19) 0.011 (2) 0.023 (2)C18 0.043 (3) 0.030 (3) 0.029 (2) 0.006 (2) 0.013 (2) 0.019 (2)C19 0.038 (3) 0.037 (3) 0.041 (3) 0.013 (2) 0.022 (2) 0.013 (2)C20 0.038 (3) 0.029 (3) 0.039 (3) 0.013 (2) 0.019 (2) 0.021 (2)N12 0.031 (2) 0.027 (2) 0.032 (2) 0.0085 (16) 0.0155 (17) 0.0119 (17)O2 0.044 (2) 0.079 (3) 0.046 (2) 0.0153 (18) 0.0187 (17) 0.028 (2)Geometric parameters (Å, º) Cu1—O1 1.929 (3) N11—C11 1.338 (5)Cu1—O3 1.930 (3) N11—C15 1.345 (5)Cu1—N12 1.984 (3) C11—C12 1.371 (5)Cu1—N11 2.006 (3) C11—H11 0.9500Cu1—Cl1 2.5944 (12) C12—C13 1.387 (5)O1—C1 1.270 (4) C12—H12 0.9500C1—C2 1.369 (5) C13—C14 1.372 (5)C1—C1i 1.537 (7) C13—H13 0.9500C2—C3 1.424 (5) C14—C15 1.383 (5)data reportsdata-4IUCrData (2023). 8, x230713    C2—H2 0.9500 C14—H14 0.9500O3—C3 1.275 (4) C15—C16 1.481 (5)C3—C4 1.485 (5) C16—N12 1.371 (5)C4—C5 1.390 (5) C16—C17 1.384 (5)C4—C9 1.412 (5) C17—C18 1.396 (5)C5—C6 1.374 (6) C17—H17 0.9500C5—H5 0.9500 C18—C19 1.393 (5)C6—C7 1.378 (6) C18—H18 0.9500C6—H6 0.9500 C19—C20 1.375 (5)C7—C8 1.385 (6) C19—H19 0.9500C7—H7 0.9500 C20—N12 1.352 (5)C8—C9 1.378 (5) C20—H20 0.9500C8—H8 0.9500 O2—H2A 0.82 (5)C9—H9 0.9500 O2—H2B 0.98 (4)O1—Cu1—O3 93.44 (11) C4—C9—H9 119.4O1—Cu1—N12 89.27 (12) C11—N11—C15 118.8 (3)O3—Cu1—N12 167.52 (12) C11—N11—Cu1 125.9 (3)O1—Cu1—N11 163.37 (13) C15—N11—Cu1 115.3 (3)O3—Cu1—N11 93.59 (12) N11—C11—C12 122.1 (4)N12—Cu1—N11 80.78 (13) N11—C11—H11 118.9O1—Cu1—Cl1 95.59 (9) C12—C11—H11 118.9O3—Cu1—Cl1 94.10 (9) C11—C12—C13 119.3 (4)N12—Cu1—Cl1 97.76 (10) C11—C12—H12 120.4N11—Cu1—Cl1 98.92 (9) C13—C12—H12 120.4C1—O1—Cu1 122.0 (2) C14—C13—C12 118.9 (4)O1—C1—C2 126.3 (4) C14—C13—H13 120.6O1—C1—C1i 115.8 (4) C12—C13—H13 120.6C2—C1—C1i 117.8 (5) C13—C14—C15 119.1 (4)C1—C2—C3 125.1 (4) C13—C14—H14 120.4C1—C2—H2 117.4 C15—C14—H14 120.4C3—C2—H2 117.4 N11—C15—C14 121.9 (4)C3—O3—Cu1 123.6 (3) N11—C15—C16 114.7 (3)O3—C3—C2 123.4 (4) C14—C15—C16 123.5 (4)O3—C3—C4 116.9 (4) N12—C16—C17 121.7 (4)C2—C3—C4 119.7 (4) N12—C16—C15 113.3 (3)C5—C4—C9 117.5 (4) C17—C16—C15 125.0 (3)C5—C4—C3 119.9 (4) C16—C17—C18 119.7 (4)C9—C4—C3 122.6 (4) C16—C17—H17 120.2C6—C5—C4 121.2 (4) C18—C17—H17 120.2C6—C5—H5 119.4 C19—C18—C17 118.3 (4)C4—C5—H5 119.4 C19—C18—H18 120.8C5—C6—C7 120.5 (4) C17—C18—H18 120.8C5—C6—H6 119.7 C20—C19—C18 119.4 (4)C7—C6—H6 119.7 C20—C19—H19 120.3C6—C7—C8 119.9 (4) C18—C19—H19 120.3C6—C7—H7 120.0 N12—C20—C19 122.9 (4)C8—C7—H7 120.0 N12—C20—H20 118.5data reportsdata-5IUCrData (2023). 8, x230713    C9—C8—C7 119.7 (4) C19—C20—H20 118.5C9—C8—H8 120.2 C20—N12—C16 118.0 (4)C7—C8—H8 120.2 C20—N12—Cu1 126.2 (3)C8—C9—C4 121.2 (4) C16—N12—Cu1 115.9 (3)C8—C9—H9 119.4 H2A—O2—H2B 96 (4)Cu1—O1—C1—C2 −16.0 (6) C11—C12—C13—C14 −0.4 (6)Cu1—O1—C1—C1i 165.1 (3) C12—C13—C14—C15 0.1 (6)O1—C1—C2—C3 −4.0 (7) C11—N11—C15—C14 1.3 (6)C1i—C1—C2—C3 174.9 (4) Cu1—N11—C15—C14 −179.5 (3)Cu1—O3—C3—C2 12.9 (5) C11—N11—C15—C16 179.4 (3)Cu1—O3—C3—C4 −168.5 (2) Cu1—N11—C15—C16 −1.4 (4)C1—C2—C3—O3 5.8 (6) C13—C14—C15—N11 −0.6 (6)C1—C2—C3—C4 −172.7 (4) C13—C14—C15—C16 −178.5 (4)O3—C3—C4—C5 15.4 (6) N11—C15—C16—N12 1.4 (5)C2—C3—C4—C5 −166.0 (4) C14—C15—C16—N12 179.5 (3)O3—C3—C4—C9 −165.8 (4) N11—C15—C16—C17 179.8 (4)C2—C3—C4—C9 12.9 (6) C14—C15—C16—C17 −2.1 (6)C9—C4—C5—C6 −0.7 (6) N12—C16—C17—C18 −1.8 (6)C3—C4—C5—C6 178.2 (4) C15—C16—C17—C18 179.9 (4)C4—C5—C6—C7 1.2 (7) C16—C17—C18—C19 1.8 (6)C5—C6—C7—C8 −0.4 (7) C17—C18—C19—C20 −1.3 (6)C6—C7—C8—C9 −0.8 (6) C18—C19—C20—N12 0.6 (6)C7—C8—C9—C4 1.3 (6) C19—C20—N12—C16 −0.4 (6)C5—C4—C9—C8 −0.6 (6) C19—C20—N12—Cu1 179.9 (3)C3—C4—C9—C8 −179.4 (4) C17—C16—N12—C20 1.0 (6)C15—N11—C11—C12 −1.7 (6) C15—C16—N12—C20 179.5 (3)Cu1—N11—C11—C12 179.3 (3) C17—C16—N12—Cu1 −179.2 (3)N11—C11—C12—C13 1.2 (6) C15—C16—N12—Cu1 −0.7 (4)Symmetry code: (i) −x, −y+1, −z+2.Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AO2—H2A···Cl1 0.82 (5) 2.41 (5) 3.224 (3) 171 (5)O2—H2B···Cl1ii 0.98 (4) 2.33 (5) 3.307 (4) 172 (4)Symmetry code: (ii) −x, −y, −z+1.

μ-1,6-Dioxo-1,6-diphenylhexane-3,4-diolato-bis[(2,2′-bipyridine)chloridocopper(II)] dihydrate  a; b; a

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μ-1,6-Dioxo-1,6-diphenylhexane-3,4-diolato-bis[(2,2′-bipyridine)chloridocopper(II)] dihydrate a; b; a

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