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Acta Cryst. (2007). E63, m1810-m1811    [ doi:10.1107/S160053680702332X ]

Aquamalonato(1,10-phenanthroline)copper(II) sesquihydrate

M. Diallo, M. Dieng, M. Gaye, A. S. Sall, A. H. Barry and B. Chahrazed

Abstract top

In the title compound, [Cu(C3H4O4)(C12H8N2)(H2O)]·1.5H2O, there are two complex molecules and three uncoordinated water molecules in the asymmetric unit. In both complex molecules, the Cu atom is five-coordinated by one bidentate 1,10-phenanthroline molecule, one bidentate malonate dianion and one water molecule, resulting in a distorted square-based pyramidal CuN2O3 chromophore. The structure is stabilized by O-H...O hydrogen bonds involving both the coordinated and uncoordinated water molecules.

Comment top

The title compound, (I), consists of a mononuclear Cu(II) complex with two neutral molecules in the asymmetric unit (Fig. 1). The Cu(II) ion displays a five coordinated-geometry where the Cu atom is coordinated by two nitrogen atoms of one 1,10-phenanthroline ligand, two oxygen atoms of one non-bridging dicarboxylate group and one oxygen atom of a water molecule (Table 1). Furthermore the largest angles around the Cu(II) centers (β:N1—Cu2—O7=168.67 (8)° and β: N4—Cu1—O2=172.50 (8)°) are slightly larger than the second-largest ones (α: N2—Cu2—O3=164.80 (8)° and α: N3—Cu1—O1=164.14 (9)°). Since the distortion value of the coordination polyhedron, τ=(β-α)/60 is evaluated by the two largest angles in the five coordinated geometry (Addison et al. 1984), the values of τ=0.14 for Cu1 and τ=0.06 for Cu2 which can be compared with the ideal values of 1 for a trigonal-bipyramidal and 0 for a square-pyramidal seem to indicate a distorted square pyramidal geometry around the two Cu centers. Atoms [O1, O2, N4 and N3] and [O3, O7, N1 and N2] consist of a square planar geometry with some deviation from perfect square plane. The apical positions are occupied by O6 and O10 respectively. The malonate ligand afforded two deprotonated carboxylate groups leading to a dinegative charge on the ligand. The structure of (I) is stablisied by O—H···O hydrogen bonds (Table 2).

This structure is comparable to that of [Cu(L-glu)(phen)(H2O)] (Anitolini et al. 1985) in which the Cu ions also have distorted square-pyramidal coordination geometry comprised of a bidentate phenanthroline ligand and an O,N-bidentate glutamate dianion and an apical coordination water O atom. The Cu—Owater lengths are 2.303 (2) and 2.268 (2) Å in the two molecules, slighly shorter than the value of 2.332 (4) Å observed for Cu—Owater Å in the complex [Cu(Hdapsox)(H2O)](ClO4) where H2dapsox is 2',2'''-(2,6-pyridindiyldiethylidene) dioxamohydrazide (Ivanovic-Burmazovic et al. 1998) but similar to that observed in the complex [Cu2(mal)2(IX)(H2O)6]n (Chawla et al. 2004) where IX is 1,4-bis(imidazole-1-yl-methylene)benzene) (2.277 Å).

Related literature top

For related structures: see Anitolini et al. (1985); Ivanovic-Burmazovic et al. (1998); Chawla et al., (2004). For related literature, see: Addison et al. (1984); Farrugia (1997).

Experimental top

Into an aqueous solution (5 ml) of Cu(NO3)2 3H2O (0.3011 g, 1.25 mmol) was poured 1.5 ml of a molar solution of Na2CO3. The mixture was stirred for 5 minutes and centrifuged. The solid which was isolated was added into a methanolic solution (10 ml) of 1,10-phenanthroline monohydrate (0.2478 g, 1.25 mmol) and malonic acid (0.1301 g, 1.25 mmol). The resulting mixture was heated at 343 K for thirty minutes. The green solution was filtered and then allowed to evaporate slowly in an open atmosphere. After one week, green crystals of (I) were obtained. The crystals were separated, washed with cold methanol and dried (yield: 65%, based on Cu(NO3)2 3H2O); Anal. Calc. for C30H30Cu2N4O13: C, 46.10; H, 3.87; N, 7.17%. Found: C, 46.06; H, 3.85; N, 7.19%.

Refinement top

The O-bound H atoms were located in a difference map and refined as riding in their as found relative positions with a fixed Uiso of 0.062 Å2. The C-bound H atoms were placed geometrically (C—H = 0.950.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Nonius, 1998); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of the asymmetric unit of (I) with displacement ellipsoids plotted at the 50% probability level (arbitrary spheres for the H atoms).
Aquamalonato(1,10-phenanthroline)copper(II) sesquihydrate top
Crystal data top
[Cu(C3H4O4)(C12H8N2)(H2O)]·1.5H2OZ = 4
Mr = 390.84F000 = 800
Triclinic, P1Dx = 1.696 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71069 Å
a = 11.5591 (2) ÅCell parameters from 12012 reflections
b = 11.7450 (2) Åθ = 1.0–30.0º
c = 12.5081 (2) ŵ = 1.47 mm−1
α = 92.177 (1)ºT = 173 (2) K
β = 105.457 (1)ºPrism, green
γ = 109.1821 (8)º0.10 × 0.10 × 0.05 mm
V = 1531.06 (5) Å3
Data collection top
Nonius Kappa CCD
diffractometer		6592 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Monochromator: graphiteθmax = 30.0º
T = 173(2) Kθmin = 1.7º
ω and φ scansh = −16→16
Absorption correction: nonek = −16→15
21966 measured reflectionsl = −17→17
8939 independent reflections
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.124  w = 1/[σ2(Fo2) + (0.0621P)2 + 0.2273P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
8939 reflectionsΔρmax = 0.58 e Å−3
442 parametersΔρmin = −0.74 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cu(C3H4O4)(C12H8N2)(H2O)]·1.5H2Oγ = 109.1821 (8)º
Mr = 390.84V = 1531.06 (5) Å3
Triclinic, P1Z = 4
a = 11.5591 (2) ÅMo Kα
b = 11.7450 (2) ŵ = 1.47 mm−1
c = 12.5081 (2) ÅT = 173 (2) K
α = 92.177 (1)º0.10 × 0.10 × 0.05 mm
β = 105.457 (1)º
Data collection top
Nonius Kappa CCD
diffractometer		8939 independent reflections
Absorption correction: none6592 reflections with I > 2σ(I)
21966 measured reflectionsRint = 0.044
Refinement top
R[F2 > 2σ(F2)] = 0.046442 parameters
wR(F2) = 0.124H-atom parameters constrained
S = 1.07Δρmax = 0.58 e Å−3
8939 reflectionsΔρmin = −0.74 e Å−3
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 > 2sigma(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
Cu10.83061 (3)0.35565 (3)0.64500 (2)0.03168 (9)
Cu20.71496 (3)0.06782 (3)0.97437 (2)0.02830 (9)
O10.86279 (19)0.36223 (17)0.80482 (13)0.0398 (4)
O20.7194 (2)0.4471 (2)0.62900 (14)0.0491 (5)
O30.71195 (19)0.03964 (18)0.82197 (13)0.0404 (4)
O40.7521 (2)−0.03321 (19)0.67820 (14)0.0474 (5)
O50.84700 (18)0.42129 (17)0.96762 (13)0.0387 (4)
O60.6375 (2)0.5720 (2)0.68385 (17)0.0643 (7)
O70.78901 (17)−0.05295 (16)1.02331 (13)0.0362 (4)
O80.88860 (19)−0.18133 (18)1.01234 (15)0.0441 (5)
O90.67258 (18)0.16762 (18)0.58759 (15)0.0442 (5)
O100.90425 (16)0.22466 (16)1.03827 (13)0.0348 (4)
O110.7673 (2)0.5795 (2)1.08301 (16)0.0530 (5)
O120.4202 (2)0.1567 (2)0.52647 (18)0.0660 (6)
O130.6054 (2)0.6153 (2)0.45161 (19)0.0718 (7)
N10.60609 (19)0.17145 (19)0.92857 (15)0.0289 (4)
N20.66727 (19)0.08302 (19)1.11745 (15)0.0300 (4)
N30.8475 (2)0.38116 (18)0.48948 (15)0.0307 (4)
N40.95203 (19)0.26891 (19)0.64407 (15)0.0302 (4)
C10.5672 (2)0.2071 (2)1.01363 (18)0.0281 (5)
C21.0673 (3)0.1905 (3)0.4113 (2)0.0458 (7)
H11.11700.14600.39410.055*
C30.4628 (3)0.3173 (3)1.0999 (2)0.0411 (6)
H20.41830.37291.09560.049*
C40.8381 (2)0.4326 (2)0.86825 (18)0.0294 (5)
C50.8384 (2)−0.1090 (2)0.97004 (19)0.0303 (5)
C60.7621 (2)−0.0238 (2)0.77940 (18)0.0310 (5)
C71.0521 (3)0.1971 (2)0.5215 (2)0.0374 (6)
C80.5733 (2)0.2109 (2)0.8310 (2)0.0361 (6)
H30.59920.18610.77080.043*
C90.4924 (3)0.2704 (3)1.1961 (2)0.0411 (6)
H40.46710.29261.25770.049*
C100.4974 (2)0.2848 (2)1.0038 (2)0.0347 (5)
C110.7124 (3)0.5173 (2)0.7043 (2)0.0367 (6)
C120.4645 (3)0.3256 (3)0.8995 (2)0.0433 (6)
H50.41700.37880.88880.052*
C131.0119 (3)0.2465 (3)0.3323 (2)0.0444 (7)
H61.02190.23930.25960.053*
C140.7998 (3)0.5366 (2)0.82237 (19)0.0387 (6)
H70.75800.56320.87310.046*
H80.87950.60530.82760.046*
C150.5996 (2)0.1581 (2)1.11580 (18)0.0277 (5)
C160.7976 (3)0.4437 (2)0.41560 (19)0.0360 (6)
H90.74850.48720.43550.043*
C170.5615 (2)0.1877 (2)1.20699 (19)0.0332 (5)
C180.9751 (2)0.2590 (2)0.54358 (18)0.0296 (5)
C190.6969 (3)0.0339 (3)1.2106 (2)0.0376 (6)
H100.7440−0.01921.21300.045*
C200.5945 (3)0.1345 (3)1.3033 (2)0.0404 (6)
H110.57060.15191.36740.048*
C211.1090 (3)0.1438 (3)0.6107 (2)0.0528 (8)
H121.16340.10130.60060.063*
C220.8396 (3)−0.0902 (3)0.8508 (2)0.0403 (6)
H130.9302−0.04740.85420.048*
H140.8134−0.17210.80860.048*
C231.0055 (3)0.2159 (3)0.72536 (19)0.0384 (6)
H150.98860.22080.79530.046*
C240.9179 (2)0.3201 (2)0.45969 (18)0.0293 (5)
C250.9382 (2)0.3168 (2)0.35420 (19)0.0341 (5)
C260.8837 (3)0.3834 (3)0.27801 (19)0.0396 (6)
H160.89430.38410.20520.048*
C270.8157 (3)0.4470 (3)0.3094 (2)0.0407 (6)
H170.78040.49380.25890.049*
C280.6612 (3)0.0576 (3)1.3048 (2)0.0434 (7)
H180.68320.02041.36960.052*
C290.5015 (3)0.2878 (3)0.8138 (2)0.0430 (6)
H190.47880.31370.74260.052*
C301.0856 (3)0.1536 (3)0.7115 (2)0.0517 (8)
H201.12360.11810.77180.062*
H210.61330.59930.52720.062*
H220.53570.54150.42280.062*
H230.39960.22830.53230.062*
H240.36400.12620.45840.062*
H250.81370.65891.06260.062*
H260.78330.52241.05220.062*
H270.90930.29351.01320.062*
H280.96740.21141.01530.062*
H290.68250.10330.62300.062*
H300.58090.14320.57010.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.04086 (18)0.04053 (19)0.02340 (14)0.02651 (15)0.00992 (12)0.00430 (12)
Cu20.03470 (17)0.03519 (18)0.02483 (14)0.02200 (14)0.01212 (12)0.00651 (11)
O10.0572 (12)0.0509 (12)0.0259 (8)0.0380 (10)0.0119 (8)0.0046 (7)
O20.0648 (13)0.0685 (14)0.0297 (9)0.0510 (12)0.0057 (8)−0.0006 (8)
O30.0582 (12)0.0535 (12)0.0259 (8)0.0391 (10)0.0142 (8)0.0092 (8)
O40.0661 (13)0.0620 (14)0.0255 (8)0.0366 (11)0.0141 (8)0.0055 (8)
O50.0548 (11)0.0444 (11)0.0273 (8)0.0286 (9)0.0146 (8)0.0074 (7)
O60.0869 (17)0.0887 (18)0.0454 (11)0.0738 (15)0.0117 (11)0.0028 (11)
O70.0535 (11)0.0428 (11)0.0302 (8)0.0336 (9)0.0194 (8)0.0108 (7)
O80.0596 (12)0.0521 (12)0.0445 (10)0.0422 (10)0.0240 (9)0.0190 (9)
O90.0456 (11)0.0453 (12)0.0398 (9)0.0166 (9)0.0079 (8)0.0119 (8)
O100.0359 (9)0.0394 (10)0.0352 (8)0.0191 (8)0.0124 (7)0.0093 (7)
O110.0723 (14)0.0597 (14)0.0483 (11)0.0393 (12)0.0308 (10)0.0139 (10)
O120.0638 (15)0.0736 (16)0.0508 (12)0.0323 (13)−0.0077 (10)0.0003 (11)
O130.0708 (16)0.0746 (18)0.0614 (14)0.0227 (14)0.0070 (12)0.0268 (12)
N10.0306 (10)0.0342 (11)0.0268 (9)0.0164 (9)0.0098 (8)0.0056 (8)
N20.0332 (10)0.0361 (11)0.0286 (9)0.0183 (9)0.0138 (8)0.0070 (8)
N30.0363 (11)0.0318 (11)0.0268 (9)0.0160 (9)0.0085 (8)0.0055 (8)
N40.0347 (11)0.0371 (12)0.0251 (9)0.0193 (9)0.0104 (8)0.0059 (8)
C10.0257 (11)0.0308 (13)0.0301 (11)0.0123 (10)0.0094 (9)0.0030 (9)
C20.0519 (17)0.0580 (19)0.0436 (14)0.0297 (15)0.0270 (13)0.0059 (13)
C30.0392 (14)0.0419 (16)0.0520 (15)0.0245 (13)0.0170 (12)0.0007 (12)
C40.0324 (12)0.0333 (13)0.0254 (10)0.0152 (11)0.0084 (9)0.0033 (9)
C50.0332 (12)0.0314 (13)0.0314 (11)0.0172 (11)0.0104 (10)0.0045 (9)
C60.0352 (13)0.0354 (14)0.0255 (10)0.0151 (11)0.0106 (9)0.0030 (9)
C70.0396 (14)0.0447 (16)0.0376 (12)0.0224 (12)0.0174 (11)0.0051 (11)
C80.0380 (14)0.0429 (16)0.0326 (12)0.0196 (12)0.0112 (10)0.0095 (10)
C90.0387 (14)0.0477 (17)0.0447 (14)0.0216 (13)0.0184 (11)−0.0056 (12)
C100.0323 (13)0.0347 (14)0.0424 (13)0.0175 (11)0.0125 (10)0.0041 (10)
C110.0455 (15)0.0423 (15)0.0332 (12)0.0267 (13)0.0145 (11)0.0088 (11)
C120.0421 (15)0.0402 (16)0.0566 (16)0.0257 (13)0.0145 (13)0.0131 (12)
C130.0512 (17)0.0552 (18)0.0359 (13)0.0210 (14)0.0248 (12)0.0052 (12)
C140.0581 (17)0.0343 (14)0.0293 (11)0.0244 (13)0.0114 (11)0.0045 (10)
C150.0268 (11)0.0265 (12)0.0307 (11)0.0099 (10)0.0097 (9)0.0015 (9)
C160.0438 (15)0.0357 (14)0.0313 (11)0.0193 (12)0.0085 (10)0.0069 (10)
C170.0308 (12)0.0386 (14)0.0313 (11)0.0117 (11)0.0127 (10)−0.0009 (10)
C180.0310 (12)0.0304 (13)0.0287 (11)0.0117 (10)0.0102 (9)0.0030 (9)
C190.0392 (14)0.0465 (16)0.0356 (12)0.0238 (12)0.0130 (11)0.0120 (11)
C200.0413 (14)0.0526 (17)0.0312 (12)0.0175 (13)0.0167 (11)0.0019 (11)
C210.0603 (19)0.074 (2)0.0484 (15)0.0495 (18)0.0222 (14)0.0155 (15)
C220.0518 (16)0.0550 (17)0.0331 (12)0.0365 (14)0.0200 (11)0.0131 (11)
C230.0467 (15)0.0491 (16)0.0290 (11)0.0278 (13)0.0123 (11)0.0101 (11)
C240.0323 (12)0.0289 (12)0.0260 (10)0.0098 (10)0.0089 (9)0.0022 (9)
C250.0360 (13)0.0369 (14)0.0271 (11)0.0084 (11)0.0114 (10)0.0019 (10)
C260.0432 (15)0.0462 (16)0.0261 (11)0.0096 (13)0.0119 (10)0.0084 (10)
C270.0456 (15)0.0421 (16)0.0314 (12)0.0149 (13)0.0060 (11)0.0141 (11)
C280.0482 (16)0.0593 (19)0.0282 (12)0.0228 (14)0.0139 (11)0.0153 (11)
C290.0451 (15)0.0505 (17)0.0422 (14)0.0262 (14)0.0132 (12)0.0196 (12)
C300.064 (2)0.069 (2)0.0434 (15)0.0492 (18)0.0163 (14)0.0184 (14)
Geometric parameters (Å, °) top
Cu1—O21.9061 (18)C3—C101.440 (3)
Cu1—O11.9270 (16)C3—H20.9500
Cu1—N41.989 (2)C4—C141.513 (3)
Cu1—N32.0298 (19)C5—C221.519 (3)
Cu1—O92.293 (2)C6—C221.514 (3)
Cu2—O31.9114 (16)C7—C181.392 (3)
Cu2—O71.9246 (16)C7—C211.415 (4)
Cu2—N12.017 (2)C8—C291.401 (4)
Cu2—N22.0260 (18)C8—H30.9500
Cu2—O102.2643 (18)C9—C171.436 (4)
O1—C41.273 (3)C9—H40.9500
O5—C41.235 (3)C10—C121.408 (4)
O2—C111.264 (3)C11—C141.511 (3)
O6—C111.219 (3)C12—C291.364 (4)
O7—C51.272 (3)C12—H50.9500
O8—C51.238 (3)C13—C251.432 (4)
O3—C61.263 (3)C13—H60.9500
O4—C61.237 (3)C14—H70.9900
O9—H290.914C14—H80.9900
O9—H300.962C15—C171.398 (3)
O10—H270.868C16—C271.399 (3)
O10—H280.907C16—H90.9500
O11—H250.993C17—C201.398 (4)
O11—H260.856C18—C241.432 (3)
O12—H230.952C19—C281.394 (4)
O12—H240.897C19—H100.9500
O13—H210.957C20—C281.365 (4)
O13—H220.944C20—H110.9500
N1—C81.326 (3)C21—C301.367 (4)
N1—C11.362 (3)C21—H120.9500
N2—C191.333 (3)C22—H130.9900
N2—C151.355 (3)C22—H140.9900
N3—C161.331 (3)C23—C301.394 (4)
N3—C241.357 (3)C23—H150.9500
N4—C231.330 (3)C24—C251.402 (3)
N4—C181.361 (3)C25—C261.406 (4)
C1—C101.391 (3)C26—C271.364 (4)
C1—C151.431 (3)C26—H160.9500
C2—C131.346 (4)C27—H170.9500
C2—C71.438 (3)C28—H180.9500
C2—H10.9500C29—H190.9500
C3—C91.350 (4)C30—H200.9500
O2—Cu1—O194.22 (7)C17—C9—H4119.4
O2—Cu1—N4172.50 (8)C1—C10—C12117.3 (2)
O1—Cu1—N492.40 (7)C1—C10—C3118.3 (2)
O2—Cu1—N390.83 (8)C12—C10—C3124.3 (2)
O1—Cu1—N3164.15 (9)O6—C11—O2121.6 (2)
N4—Cu1—N381.87 (8)O6—C11—C14118.5 (2)
O2—Cu1—O996.55 (8)O2—C11—C14119.9 (2)
O1—Cu1—O999.84 (8)C29—C12—C10119.2 (2)
N4—Cu1—O985.78 (8)C29—C12—H5120.4
N3—Cu1—O994.49 (7)C10—C12—H5120.4
O3—Cu2—O794.75 (7)C2—C13—C25122.0 (2)
O3—Cu2—N189.31 (7)C2—C13—H6119.0
O7—Cu2—N1168.67 (8)C25—C13—H6119.0
O3—Cu2—N2164.81 (8)C11—C14—C4119.5 (2)
O7—Cu2—N292.39 (7)C11—C14—H7107.4
N1—Cu2—N281.31 (8)C4—C14—H7107.4
O3—Cu2—O1099.15 (7)C11—C14—H8107.4
O7—Cu2—O1093.79 (7)C4—C14—H8107.4
N1—Cu2—O1096.00 (7)H7—C14—H8107.0
N2—Cu2—O1093.73 (7)N2—C15—C17123.3 (2)
C4—O1—Cu1126.47 (15)N2—C15—C1116.27 (19)
C11—O2—Cu1127.43 (16)C17—C15—C1120.4 (2)
C6—O3—Cu2129.19 (15)N3—C16—C27121.8 (2)
C5—O7—Cu2127.87 (15)N3—C16—H9119.1
Cu1—O9—H29119.3C27—C16—H9119.1
Cu1—O9—H30131.1C15—C17—C20117.2 (2)
Cu2—O10—H27117.8C15—C17—C9118.3 (2)
Cu2—O10—H28112.6C20—C17—C9124.6 (2)
H29—O9—H3098.1N4—C18—C7123.6 (2)
H27—O10—H2898.2N4—C18—C24116.0 (2)
H25—O11—H26110.1C7—C18—C24120.4 (2)
H23—O12—H2494.7N2—C19—C28122.4 (2)
H21—O13—H2292.2N2—C19—H10118.8
C8—N1—C1118.1 (2)C28—C19—H10118.8
C8—N1—Cu2128.98 (16)C28—C20—C17119.6 (2)
C1—N1—Cu2112.87 (15)C28—C20—H11120.2
C19—N2—C15117.8 (2)C17—C20—H11120.2
C19—N2—Cu2129.25 (17)C30—C21—C7119.7 (3)
C15—N2—Cu2112.89 (15)C30—C21—H12120.1
C16—N3—C24118.3 (2)C7—C21—H12120.1
C16—N3—Cu1129.80 (17)C6—C22—C5123.0 (2)
C24—N3—Cu1111.89 (15)C6—C22—H13106.6
C23—N4—C18118.1 (2)C5—C22—H13106.6
C23—N4—Cu1128.45 (16)C6—C22—H14106.6
C18—N4—Cu1113.33 (15)C5—C22—H14106.6
N1—C1—C10123.3 (2)H13—C22—H14106.5
N1—C1—C15116.3 (2)N4—C23—C30122.3 (2)
C10—C1—C15120.4 (2)N4—C23—H15118.8
C13—C2—C7120.7 (2)C30—C23—H15118.8
C13—C2—H1119.7N3—C24—C25123.5 (2)
C7—C2—H1119.7N3—C24—C18116.46 (19)
C9—C3—C10121.3 (2)C25—C24—C18120.1 (2)
C9—C3—H2119.4C24—C25—C26116.8 (2)
C10—C3—H2119.4C24—C25—C13118.0 (2)
O5—C4—O1122.5 (2)C26—C25—C13125.2 (2)
O5—C4—C14118.1 (2)C27—C26—C25119.5 (2)
O1—C4—C14119.4 (2)C27—C26—H16120.2
O8—C5—O7122.1 (2)C25—C26—H16120.2
O8—C5—C22116.2 (2)C26—C27—C16120.2 (2)
O7—C5—C22121.7 (2)C26—C27—H17119.9
O4—C6—O3121.8 (2)C16—C27—H17119.9
O4—C6—C22117.0 (2)C20—C28—C19119.6 (2)
O3—C6—C22121.23 (19)C20—C28—H18120.2
C18—C7—C21116.6 (2)C19—C28—H18120.2
C18—C7—C2118.7 (2)C12—C29—C8119.9 (2)
C21—C7—C2124.7 (2)C12—C29—H19120.1
N1—C8—C29122.2 (2)C8—C29—H19120.1
N1—C8—H3118.9C21—C30—C23119.6 (3)
C29—C8—H3118.9C21—C30—H20120.2
C3—C9—C17121.3 (2)C23—C30—H20120.2
C3—C9—H4119.4
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O9—H29···O40.912.082.961 (3)161
O9—H30···O120.961.852.769 (3)158
O10—H27···O50.871.912.720 (3)154
O10—H28···O8i0.911.922.824 (3)172
O11—H25···O8ii0.991.992.983 (3)174
O11—H26···O50.861.992.831 (3)167
O12—H23···O13iii0.951.862.800 (3)168
O12—H24···O4iv0.901.892.780 (3)169
O13—H21···O60.961.962.915 (3)177
O13—H22···O6iii0.942.062.952 (3)156
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1.
Selected geometric parameters (Å) top
Cu1—O21.9061 (18)Cu2—O31.9114 (16)
Cu1—O11.9270 (16)Cu2—O71.9246 (16)
Cu1—N41.989 (2)Cu2—N12.017 (2)
Cu1—N32.0298 (19)Cu2—N22.0260 (18)
Cu1—O92.293 (2)Cu2—O102.2643 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O9—H29···O40.912.082.961 (3)161
O9—H30···O120.961.852.769 (3)158
O10—H27···O50.871.912.720 (3)154
O10—H28···O8i0.911.922.824 (3)172
O11—H25···O8ii0.991.992.983 (3)174
O11—H26···O50.861.992.831 (3)167
O12—H23···O13iii0.951.862.800 (3)168
O12—H24···O4iv0.901.892.780 (3)169
O13—H21···O60.961.962.915 (3)177
O13—H22···O6iii0.942.062.952 (3)156
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1.
Acknowledgements top

The authors thank the Agence Universitaire de la Francophonie for financial support (AUF-PSCI No. 6301PS48).

references
References top

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