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Acta Cryst. (2008). E64, m394    [ doi:10.1107/S1600536808001980 ]

Bis[(2-quinolyl)methanediol-[kappa]2N,O](sulfato-[kappa]O)copper(II) dihydrate

N. D. Martins, J. A. Silva, M. Ramos Silva, A. Matos Beja and A. J. F. N. Sobral

Abstract top

In the title compound, [Cu(SO4)(C10H9NO2)2]·2H2O, the CuII ion is chelated by two (2-quinolyl)methanediol ligands and coordinated by a monodentate sulfate ligand in a distorted trigonal-bipyramidal environment, with O atoms occupying the equatorial sites and N atoms in the axial sites. The dihedral angle between the two essentially planar quinoline ring systems is 45.02 (9)°. In the crystal structure, an extensive O-H...O hydrogen-bonding network forms layers parallel to the ab plane.

Comment top

Seeking new compounds with low dimensional elements (such as dimers or chains) that may exhibit interesting magnetic properties, we have obtained the title compound, [Cu(C10H9NO2)(SO4)].2H2O, Fig. 1. There are some examples in literature, where quinoline derivatives ligands were successfully used in the synthesis of compounds with magnetic interactions (Zurowska et al., 2007; Dobrzynska et al., 2005; Kumar & Gandotra, 1980; Catterick et al., 1974). In the title compound, the CuII ion is surrounded by 5 atoms, 3 oxygen atoms in equatorial positions and two nitrogen atoms in the axial positions delineating a distorted bipyramidal coordination geometry. In the equatorial plane, two of the oxygen atoms are supplied by the hydroxy groups of two symmetry independent quinoline derivatives. The remaining equatorial O atom belongs to a sulfato dinegative ion. The two quinoline derivatives are similar, with the chelating hydroxy groups approximmately sharing the ring plane [O1—C1—C2—N1 - 12.5 (3), O2—C1—C2—N1 109.7 (2)°, and O3—C11—C12—N2 - 1.9 (3), O4—C11—C12—N2 119.0 (2)°]. There is an extensive network of hydrogen bonds forming layers parallel to the ab plane (Fig.2 & Fig. 3). The two solvent water molecules are essential in the network formation since they exhaust their capacity of donating and accepting protons. Each pair of water molecules aggregates 3 metal complexes.

.

Related literature top

For related literature, see: Zurowska et al. (2007); Dobrzynska et al. (2005); Kumar & Gandotra (1980); Catterick et al. (1974).

Experimental top

Approximately 0.13 mmol of 2-quinolinecarboxaldehyde (Sigma, 97%) were dissolved in 2 ml of dichloromethane and then 0.13 mmol of copper sulfate were added to the solution. After one month, single crystals of suitable quality were grown from the solution.

Refinement top

All H-atoms could be located in a Fourier difference map. Aromatic H atoms were positioned geometrically and refined using a riding- model with C—H = 0.93 Å, Uiso(H) = 1.2Ueq(C). Hydroxy and water hydrogen atoms were refined with a distance restraint to their parent O atoms (0.82 and 0.85 Å, respectively), starting from the difference map coordinates and with Uiso(H) = 1.5Ueq(O). There is a short intermolecular contact (H3A ···H101 2.01 Å).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% level.
[Figure 2] Fig. 2. A portion of the H-bond network viewed along the c axis. The hydrohen bonds are depicted as dashed lines.
[Figure 3] Fig. 3. Packing of the title compound, viewed along the a axis. The hydrogen bonds are depicted as dashed lines.
Bis[(2-quinolyl)methanediol-κ2N,O](sulfato-κO)copper(II) dihydrate top
Crystal data top
[Cu(SO4)(C10H9NO2)2]·2H2OZ = 2
Mr = 546.00F000 = 562
Triclinic, P1Dx = 1.682 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 7.6065 (3) ÅCell parameters from 4898 reflections
b = 8.8747 (4) Åθ = 2.4–27.5º
c = 17.5035 (9) ŵ = 1.17 mm−1
α = 98.561 (3)ºT = 293 (2) K
β = 94.324 (3)ºBlock, green
γ = 111.305 (2)º0.24 × 0.15 × 0.12 mm
V = 1077.76 (9) Å3
Data collection top
Bruker APEX CCD area-detector
diffractometer		5289 independent reflections
Radiation source: fine-focus sealed tube3972 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 293(2) Kθmax = 28.4º
φ and ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		h = −10→10
Tmin = 0.810, Tmax = 0.864k = −11→11
18073 measured reflectionsl = −23→22
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.090  w = 1/[σ2(Fo2) + (0.0404P)2 + 0.5543P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
5289 reflectionsΔρmax = 0.36 e Å−3
331 parametersΔρmin = −0.34 e Å−3
8 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cu(SO4)(C10H9NO2)2]·2H2Oγ = 111.305 (2)º
Mr = 546.00V = 1077.76 (9) Å3
Triclinic, P1Z = 2
a = 7.6065 (3) ÅMo Kα
b = 8.8747 (4) ŵ = 1.17 mm−1
c = 17.5035 (9) ÅT = 293 (2) K
α = 98.561 (3)º0.24 × 0.15 × 0.12 mm
β = 94.324 (3)º
Data collection top
Bruker APEX CCD area-detector
diffractometer		5289 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		3972 reflections with I > 2σ(I)
Tmin = 0.810, Tmax = 0.864Rint = 0.037
18073 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0388 restraints
wR(F2) = 0.090H atoms treated by a mixture of
independent and constrained refinement
S = 1.00Δρmax = 0.36 e Å−3
5289 reflectionsΔρmin = −0.34 e Å−3
331 parameters
Special details top

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) top
xyzUiso*/Ueq
Cu10.34983 (4)0.15697 (4)0.247112 (17)0.02622 (9)
S10.62616 (8)−0.03258 (7)0.26884 (3)0.02588 (14)
O10.0893 (2)−0.0211 (3)0.26309 (11)0.0385 (4)
H1A−0.017 (3)−0.040 (4)0.2454 (19)0.058*
O20.1228 (3)−0.2200 (3)0.32675 (13)0.0452 (5)
H2A0.233 (3)−0.201 (4)0.315 (2)0.068*
O30.3080 (3)0.3702 (2)0.24886 (10)0.0349 (4)
H3A0.198 (3)0.362 (4)0.2561 (18)0.052*
O40.4924 (4)0.5501 (3)0.17828 (14)0.0576 (6)
H4A0.499 (6)0.631 (4)0.2102 (19)0.086*
O50.5547 (3)0.0768 (2)0.22997 (10)0.0365 (4)
O60.7384 (2)−0.0907 (2)0.21500 (10)0.0350 (4)
O70.4641 (3)−0.1762 (2)0.27989 (12)0.0427 (5)
O80.7444 (3)0.0593 (2)0.34206 (10)0.0378 (4)
N10.3830 (3)0.1802 (3)0.36291 (11)0.0264 (4)
N20.2914 (3)0.1435 (2)0.13256 (11)0.0262 (4)
C10.0981 (4)−0.0705 (3)0.33518 (15)0.0336 (6)
H1−0.0220−0.08460.35580.040*
C20.2594 (3)0.0620 (3)0.39163 (14)0.0297 (5)
C30.2741 (4)0.0530 (4)0.47104 (16)0.0374 (6)
H30.1860−0.03360.48880.045*
C40.4189 (4)0.1726 (4)0.52174 (15)0.0389 (6)
H40.43060.16840.57460.047*
C50.5511 (4)0.3028 (3)0.49378 (14)0.0316 (6)
C60.5303 (3)0.3033 (3)0.41296 (14)0.0272 (5)
C70.6616 (4)0.4320 (3)0.38398 (15)0.0338 (6)
H70.65010.43270.33080.041*
C80.8053 (4)0.5555 (4)0.43358 (17)0.0399 (6)
H80.89110.64010.41380.048*
C90.8259 (4)0.5572 (4)0.51402 (17)0.0424 (7)
H90.92420.64280.54720.051*
C100.7021 (4)0.4336 (4)0.54333 (16)0.0399 (7)
H100.71680.43500.59670.048*
C110.3207 (4)0.4235 (3)0.17647 (15)0.0356 (6)
H110.21680.46090.16510.043*
C120.3067 (3)0.2843 (3)0.11182 (14)0.0292 (5)
C130.3066 (4)0.3061 (3)0.03416 (15)0.0380 (6)
H130.32090.40790.02190.046*
C140.2855 (4)0.1769 (4)−0.02309 (15)0.0403 (7)
H140.28840.1905−0.07470.048*
C150.2594 (4)0.0225 (3)−0.00399 (15)0.0333 (6)
C160.2611 (3)0.0077 (3)0.07554 (14)0.0275 (5)
C170.2298 (4)−0.1460 (3)0.09590 (16)0.0365 (6)
H170.2320−0.15660.14800.044*
C180.1964 (4)−0.2788 (4)0.03934 (18)0.0449 (7)
H180.1718−0.38090.05320.054*
C190.1977 (4)−0.2669 (4)−0.03936 (18)0.0472 (7)
H190.1777−0.3595−0.07690.057*
C200.2283 (4)−0.1192 (4)−0.06075 (16)0.0432 (7)
H200.2288−0.1113−0.11310.052*
O90.8632 (4)0.5358 (4)0.20715 (17)0.0759 (8)
H910.935 (6)0.628 (4)0.236 (2)0.114*
H920.750 (4)0.541 (6)0.197 (3)0.114*
O10−0.0100 (3)0.3450 (3)0.28886 (17)0.0614 (6)
H101−0.053 (6)0.390 (5)0.256 (2)0.092*
H102−0.088 (5)0.264 (4)0.304 (2)0.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03079 (17)0.03437 (18)0.01980 (15)0.01816 (14)0.00474 (12)0.00847 (12)
S10.0268 (3)0.0326 (3)0.0227 (3)0.0163 (3)0.0031 (2)0.0060 (2)
O10.0246 (9)0.0599 (13)0.0313 (10)0.0131 (9)0.0024 (8)0.0180 (9)
O20.0360 (11)0.0419 (11)0.0577 (13)0.0124 (9)0.0078 (10)0.0147 (10)
O30.0468 (11)0.0420 (11)0.0265 (9)0.0280 (10)0.0062 (8)0.0085 (8)
O40.0752 (16)0.0319 (12)0.0560 (15)0.0091 (12)0.0173 (13)0.0046 (10)
O50.0427 (10)0.0520 (12)0.0331 (10)0.0338 (9)0.0136 (8)0.0185 (9)
O60.0350 (10)0.0490 (11)0.0279 (9)0.0267 (9)0.0036 (8)0.0009 (8)
O70.0376 (10)0.0382 (11)0.0514 (12)0.0114 (9)0.0109 (9)0.0109 (9)
O80.0420 (10)0.0446 (11)0.0263 (10)0.0200 (9)−0.0020 (8)−0.0007 (8)
N10.0295 (10)0.0361 (12)0.0212 (10)0.0189 (9)0.0077 (8)0.0098 (9)
N20.0284 (10)0.0299 (11)0.0232 (10)0.0138 (9)0.0033 (8)0.0073 (9)
C10.0284 (13)0.0435 (16)0.0345 (14)0.0155 (12)0.0105 (11)0.0164 (12)
C20.0320 (13)0.0385 (14)0.0273 (13)0.0203 (12)0.0089 (11)0.0118 (11)
C30.0447 (16)0.0439 (16)0.0328 (15)0.0210 (13)0.0145 (13)0.0204 (13)
C40.0539 (17)0.0504 (17)0.0229 (13)0.0291 (15)0.0084 (12)0.0133 (13)
C50.0387 (14)0.0424 (15)0.0229 (12)0.0255 (13)0.0052 (11)0.0071 (11)
C60.0290 (12)0.0372 (14)0.0220 (12)0.0201 (11)0.0063 (10)0.0052 (11)
C70.0369 (14)0.0427 (15)0.0261 (13)0.0182 (12)0.0105 (11)0.0085 (12)
C80.0355 (14)0.0413 (16)0.0426 (16)0.0140 (13)0.0085 (13)0.0078 (13)
C90.0399 (16)0.0475 (17)0.0391 (16)0.0216 (14)−0.0015 (13)−0.0037 (14)
C100.0467 (16)0.0537 (18)0.0256 (14)0.0299 (15)−0.0012 (12)0.0018 (13)
C110.0486 (16)0.0365 (15)0.0318 (14)0.0248 (13)0.0079 (12)0.0135 (12)
C120.0319 (13)0.0347 (14)0.0264 (13)0.0176 (11)0.0042 (10)0.0088 (11)
C130.0501 (16)0.0392 (15)0.0312 (14)0.0204 (13)0.0085 (12)0.0160 (12)
C140.0501 (17)0.0518 (18)0.0219 (13)0.0197 (14)0.0080 (12)0.0135 (13)
C150.0326 (13)0.0415 (15)0.0243 (13)0.0133 (12)0.0022 (10)0.0045 (11)
C160.0272 (12)0.0334 (13)0.0225 (12)0.0135 (11)0.0013 (10)0.0034 (10)
C170.0467 (16)0.0333 (14)0.0299 (14)0.0162 (13)0.0008 (12)0.0066 (12)
C180.0548 (18)0.0315 (15)0.0453 (18)0.0158 (14)0.0011 (14)0.0028 (13)
C190.0548 (19)0.0419 (17)0.0369 (16)0.0170 (15)−0.0004 (14)−0.0092 (14)
C200.0490 (17)0.0507 (18)0.0245 (14)0.0165 (15)0.0019 (12)−0.0013 (13)
O90.080 (2)0.0642 (17)0.0698 (19)0.0223 (16)−0.0045 (16)−0.0083 (14)
O100.0448 (13)0.0588 (16)0.0801 (19)0.0174 (12)0.0190 (13)0.0126 (14)
Geometric parameters (Å, °) top
Cu1—O51.9589 (16)C6—C71.407 (3)
Cu1—N11.9938 (19)C7—C81.361 (4)
Cu1—N21.9969 (19)C7—H70.9300
Cu1—O32.0258 (17)C8—C91.402 (4)
Cu1—O12.1080 (19)C8—H80.9300
S1—O81.4486 (19)C9—C101.357 (4)
S1—O71.4664 (19)C9—H90.9300
S1—O61.4766 (17)C10—H100.9300
S1—O51.4914 (17)C11—C121.512 (4)
O1—C11.401 (3)C11—H110.9800
O1—H1A0.79 (2)C12—C131.401 (3)
O2—C11.394 (3)C13—C141.358 (4)
O2—H2A0.84 (2)C13—H130.9300
O3—C111.415 (3)C14—C151.407 (4)
O3—H3A0.83 (2)C14—H140.9300
O4—C111.373 (3)C15—C201.414 (4)
O4—H4A0.83 (2)C15—C161.417 (3)
N1—C21.322 (3)C16—C171.402 (3)
N1—C61.376 (3)C17—C181.353 (4)
N2—C121.320 (3)C17—H170.9300
N2—C161.381 (3)C18—C191.398 (4)
C1—C21.512 (4)C18—H180.9300
C1—H10.9800C19—C201.360 (4)
C2—C31.402 (3)C19—H190.9300
C3—C41.360 (4)C20—H200.9300
C3—H30.9300O9—H910.86 (2)
C4—C51.409 (4)O9—H920.89 (2)
C4—H40.9300O10—H1010.86 (2)
C5—C61.412 (3)O10—H1020.84 (2)
C5—C101.414 (4)
O5—Cu1—N196.19 (7)N1—C6—C5120.6 (2)
O5—Cu1—N290.66 (7)C7—C6—C5119.2 (2)
N1—Cu1—N2173.14 (8)C8—C7—C6120.2 (2)
O5—Cu1—O3137.56 (8)C8—C7—H7119.9
N1—Cu1—O394.29 (7)C6—C7—H7119.9
N2—Cu1—O380.56 (7)C7—C8—C9121.0 (3)
O5—Cu1—O1115.59 (8)C7—C8—H8119.5
N1—Cu1—O179.02 (8)C9—C8—H8119.5
N2—Cu1—O198.05 (8)C10—C9—C8119.9 (3)
O3—Cu1—O1106.76 (8)C10—C9—H9120.1
O8—S1—O7111.92 (12)C8—C9—H9120.1
O8—S1—O6110.54 (10)C9—C10—C5120.9 (3)
O7—S1—O6108.23 (11)C9—C10—H10119.6
O8—S1—O5109.74 (11)C5—C10—H10119.6
O7—S1—O5109.44 (11)O4—C11—O3110.7 (2)
O6—S1—O5106.82 (10)O4—C11—C12107.5 (2)
C1—O1—Cu1112.67 (15)O3—C11—C12110.4 (2)
C1—O1—H1A111 (2)O4—C11—H11109.4
Cu1—O1—H1A131 (2)O3—C11—H11109.4
C1—O2—H2A106 (3)C12—C11—H11109.4
C11—O3—Cu1113.40 (14)N2—C12—C13122.8 (2)
C11—O3—H3A101 (2)N2—C12—C11116.6 (2)
Cu1—O3—H3A113 (2)C13—C12—C11120.6 (2)
C11—O4—H4A110 (3)C14—C13—C12119.4 (2)
S1—O5—Cu1132.80 (11)C14—C13—H13120.3
C2—N1—C6119.1 (2)C12—C13—H13120.3
C2—N1—Cu1116.29 (17)C13—C14—C15119.7 (2)
C6—N1—Cu1124.51 (16)C13—C14—H14120.1
C12—N2—C16119.3 (2)C15—C14—H14120.1
C12—N2—Cu1114.79 (16)C14—C15—C20122.9 (2)
C16—N2—Cu1125.41 (15)C14—C15—C16118.5 (2)
O2—C1—O1110.8 (2)C20—C15—C16118.6 (2)
O2—C1—C2110.6 (2)N2—C16—C17120.2 (2)
O1—C1—C2109.4 (2)N2—C16—C15120.2 (2)
O2—C1—H1108.7C17—C16—C15119.6 (2)
O1—C1—H1108.7C18—C17—C16119.6 (3)
C2—C1—H1108.7C18—C17—H17120.2
N1—C2—C3123.0 (2)C16—C17—H17120.2
N1—C2—C1117.7 (2)C17—C18—C19121.9 (3)
C3—C2—C1119.2 (2)C17—C18—H18119.1
C4—C3—C2119.2 (3)C19—C18—H18119.1
C4—C3—H3120.4C20—C19—C18119.7 (3)
C2—C3—H3120.4C20—C19—H19120.1
C3—C4—C5119.6 (2)C18—C19—H19120.1
C3—C4—H4120.2C19—C20—C15120.5 (3)
C5—C4—H4120.2C19—C20—H20119.7
C4—C5—C6118.5 (2)C15—C20—H20119.7
C4—C5—C10122.7 (2)H91—O9—H92107 (4)
C6—C5—C10118.8 (2)H101—O10—H102118 (4)
N1—C6—C7120.1 (2)
O5—Cu1—O1—C171.43 (18)C2—N1—C6—C50.8 (3)
N1—Cu1—O1—C1−20.23 (17)Cu1—N1—C6—C5−174.93 (16)
N2—Cu1—O1—C1166.06 (17)C4—C5—C6—N10.7 (3)
O3—Cu1—O1—C1−111.44 (17)C10—C5—C6—N1−178.7 (2)
O5—Cu1—O3—C1162.2 (2)C4—C5—C6—C7−179.7 (2)
N1—Cu1—O3—C11166.21 (18)C10—C5—C6—C70.9 (3)
N2—Cu1—O3—C11−18.35 (18)N1—C6—C7—C8178.8 (2)
O1—Cu1—O3—C11−113.98 (18)C5—C6—C7—C8−0.8 (3)
O8—S1—O5—Cu1−78.16 (18)C6—C7—C8—C90.1 (4)
O7—S1—O5—Cu145.01 (19)C7—C8—C9—C100.5 (4)
O6—S1—O5—Cu1161.97 (15)C8—C9—C10—C5−0.4 (4)
N1—Cu1—O5—S135.82 (18)C4—C5—C10—C9−179.7 (2)
N2—Cu1—O5—S1−144.19 (17)C6—C5—C10—C9−0.4 (4)
O3—Cu1—O5—S1139.14 (15)Cu1—O3—C11—O4−103.0 (2)
O1—Cu1—O5—S1−44.94 (19)Cu1—O3—C11—C1216.0 (3)
O5—Cu1—N1—C2−101.70 (17)C16—N2—C12—C13−4.5 (4)
O3—Cu1—N1—C2119.48 (17)Cu1—N2—C12—C13167.7 (2)
O1—Cu1—N1—C213.22 (16)C16—N2—C12—C11174.3 (2)
O5—Cu1—N1—C674.10 (18)Cu1—N2—C12—C11−13.5 (3)
O3—Cu1—N1—C6−64.71 (18)O4—C11—C12—N2119.0 (2)
O1—Cu1—N1—C6−170.97 (18)O3—C11—C12—N2−1.9 (3)
O5—Cu1—N2—C12−120.78 (17)O4—C11—C12—C13−62.2 (3)
O3—Cu1—N2—C1217.49 (17)O3—C11—C12—C13176.9 (2)
O1—Cu1—N2—C12123.25 (17)N2—C12—C13—C141.6 (4)
O5—Cu1—N2—C1650.87 (19)C11—C12—C13—C14−177.1 (3)
O3—Cu1—N2—C16−170.9 (2)C12—C13—C14—C151.6 (4)
O1—Cu1—N2—C16−65.10 (19)C13—C14—C15—C20177.2 (3)
Cu1—O1—C1—O2−99.7 (2)C13—C14—C15—C16−1.7 (4)
Cu1—O1—C1—C222.5 (2)C12—N2—C16—C17−175.1 (2)
C6—N1—C2—C3−1.9 (3)Cu1—N2—C16—C1713.6 (3)
Cu1—N1—C2—C3174.13 (18)C12—N2—C16—C154.2 (3)
C6—N1—C2—C1179.38 (19)Cu1—N2—C16—C15−167.07 (17)
Cu1—N1—C2—C1−4.6 (3)C14—C15—C16—N2−1.2 (4)
O2—C1—C2—N1109.7 (2)C20—C15—C16—N2179.9 (2)
O1—C1—C2—N1−12.5 (3)C14—C15—C16—C17178.1 (2)
O2—C1—C2—C3−69.0 (3)C20—C15—C16—C17−0.8 (4)
O1—C1—C2—C3168.7 (2)N2—C16—C17—C18178.6 (2)
N1—C2—C3—C41.6 (4)C15—C16—C17—C18−0.7 (4)
C1—C2—C3—C4−179.8 (2)C16—C17—C18—C192.0 (5)
C2—C3—C4—C50.0 (4)C17—C18—C19—C20−1.8 (5)
C3—C4—C5—C6−1.1 (4)C18—C19—C20—C150.2 (5)
C3—C4—C5—C10178.3 (2)C14—C15—C20—C19−177.9 (3)
C2—N1—C6—C7−178.8 (2)C16—C15—C20—C191.0 (4)
Cu1—N1—C6—C75.5 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O6i0.79 (3)1.77 (3)2.554 (2)174 (4)
O3—H3A···O100.83 (3)1.69 (3)2.510 (3)169 (3)
O4—H4A···O6ii0.83 (3)2.46 (4)2.992 (3)123 (3)
O4—H4A···O7ii0.83 (3)2.06 (4)2.874 (3)169 (5)
O9—H91···O2iii0.86 (4)2.00 (4)2.810 (4)157 (3)
O9—H92···O40.89 (4)2.00 (4)2.879 (5)178 (6)
O10—H101···O9i0.86 (4)1.91 (4)2.746 (4)164 (4)
O10—H102···O8i0.84 (3)2.04 (3)2.883 (3)174 (4)
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) x+1, y+1, z.
Table 1
Selected geometric parameters (Å) top
Cu1—O51.9589 (16)Cu1—O32.0258 (17)
Cu1—N11.9938 (19)Cu1—O12.1080 (19)
Cu1—N21.9969 (19)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O6i0.79 (3)1.77 (3)2.554 (2)174 (4)
O3—H3A···O100.83 (3)1.69 (3)2.510 (3)169 (3)
O4—H4A···O6ii0.83 (3)2.46 (4)2.992 (3)123 (3)
O4—H4A···O7ii0.83 (3)2.06 (4)2.874 (3)169 (5)
O9—H91···O2iii0.86 (4)2.00 (4)2.810 (4)157 (3)
O9—H92···O40.89 (4)2.00 (4)2.879 (5)178 (6)
O10—H101···O9i0.86 (4)1.91 (4)2.746 (4)164 (4)
O10—H102···O8i0.84 (3)2.04 (3)2.883 (3)174 (4)
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) x+1, y+1, z.
Acknowledgements top

This work was supported by Fundação para a Ciência e a Tecnologia (FCT) under project POCI/FIS/57876/2004.

references
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