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Acta Cryst. (2009). E65, m761-m762    [ doi:10.1107/S1600536809021588 ]

(2,9-Dimethyl-1,10-phenanthroline)(4-hydroxypyridine-2,6-dicarboxylato)copper(II) trihydrate

J. Soleimannejad, H. Aghabozorg, F. Manteghi and S. Najafi

Abstract top

In the title complex, [Cu(C7H3NO5)(C14H12N2)]·3H2O, there are two independent neutral molecules of the Cu complex along with six molecules of water of hydration in the asymmetric unit. The CuII atoms in each complex adopt a distorted square-pyramidal coordination geometry being pentacoordinated by one N and two O atoms of 4-hydroxypyridine-2,6-dicarboxylate anions and two N atoms of 2,9-dimethyl-1,10-phenanthroline (dmp) molecules. In the crystal structure, there are O-H...O and C-H...O hydrogen bonds and five [pi]-[pi] stacking interactions with centroid-centroid distances in the range 3.620 (1)-3.712 (1) Å. In addition, a C-H...[pi] interaction between a heterocyclic ring of dmp is observed to reinforce the crystal cohesion.

Comment top

There are several reports on coordination of 4-hydroxypyridine-2,6-dicarboxylic acid (H3chel or chelidamic acid) to metals, such as Fe(Hchel)Cl(H2O)2].(18-crown-6).2H2O (Zhou et al., 2007), [Zn(Hchel)(H2O)3].0.25CH3CN.H2O (Zhou et al., 2003), (tataH)2[Cu(Hchel)2.6H2O (tata: 2,4,6-triamino-1,3,5-triazine) (Ramos Silva et al., 2008), (GH)2[Ni(Hchel)2].2H2O (G: guanidine) (Aghabozorg, Motyeian & Gharamaleki et al., 2008) and {[Cd2(Hchel)2(H2O)4].4H2O}n (Aghabozorg, Ilaie et al., 2008) [Cu(Hchel)(phen)(H2O)].4.5H2O (phen: phenanthroline) (Aghabozorg, Motyeian & Gharamaleki et al., 2008; Aghabozorg, Manteghi & Sheshmani, 2008). Also, there are some reports on 2,9-dimethyl-1,10-phenanthroline (dmp) coordinated to metallic ions like [Cu(dmp)2][N(CN)2] (King et al.., 2005) and [Cu(HCO2)2(dmp)(H2O)] (Lin et al., 2008). We have now prepared the title compound, (I), which contains both Hchel and dmp species coordinated to CuII atom. In this paper, we report the crystal structure of (I).

In the asymmetric unit of (I), there are two Cu-complexe molecules which slightly differ in bond lengths and bond angles (Figs. 1 and 2). However, both units have a penta-coordinated geometry around CuII atoms.

The bond angles around CuII indicate that there are two angles near linearity for each CuII atom, N3Cu1N1, 168.68 (7)°, O5Cu1O1, 159.59 (6)°, N6Cu2N5, 168.36 (7)° and O6Cu2O10, 158.49 (6)° and the other angles are close to 90°. Therefore, the coordination polyhedra of two CuII atoms will be distorted square pyramids with N2 and N4 lying on axial positions. The bonds Cu1—N2 (2.2263 (17) Å) and Cu2—N4 (2.2281 (17) Å) are significantly longer than the remaining Cu —N bonds. This can be attributed to distortion due to d9 configuration of CuII atom.

The crystal structure contains many O—H···O and C—H···O hydrogen bonds (details are in Table 1 and Fig. 3) and various π–π stacking interactions. On the other hand, the five π–π stackings have centroid-centroid distances 3.620 (1) Å (x,y,z), 3.712 (1) Å (x - 1,y,z), 3.667 (1) Å (x,y,z), 3.597 (1) Å (x - 1,y,z - 1), 3.634 (1) Å (x - 1,y,z), the shortest is between N6/C36—C40 and N3/C16—C20 rings. Also, a C— H···π interaction (C13—H13B and π ring of N4/C22—C25,C33 (-x + 1,-y + 2,-z + 1) with distance and angle 3.372 (2) Å, 121°) is present as another interaction to the supramolecular assembly.

Related literature top

For related structures, see: Zhou et al. (2003, 2007); Ramos Silva et al. (2008); Aghabozorg, Ilaie et al. (2008); Aghabozorg, Manteghi & Sheshmani (2008); Aghabozorg, Motyeian, Gharamaleki et al. (2008); Aghabozorg, Motyeian, Soleimannejadet al. (2008); King et al. (2005); Lin et al. (2008). Cg1 is the centroid of the N4/C22–C25,C33 ring.

Experimental top

The aqeuous solution containing 2,9-dimethyl-1,10-phenanthroline (0.080 g, 0.38 mmol) and 4-hydroxypyridine-2,6-dicarboxylic acid (0.069 g, 0.38 mmol) was stirred for 15 min, then the ethanol solution of CuCl2.2H2O (0.064 g, 0.38 mmol) was carefully layered on the water solution. Blue crystals suitable for crystallography were obtained in one day.

Refinement top

All H atoms were placed geometrically and included in the refinement in riding motion approximationat with distances for methyl, aryl, hydroxyl and water hydrogen atoms being 0.98, 0.95, 0.84 and 0.85 Å, respectively, and with Uiso(H) = 1.2 or 1.5Ueq of the carrier atoms.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of one of the two independent molecules of [Cu(Hchel)(dmp)]. Thermal ellipsoids are shown at 50% probability level.
[Figure 2] Fig. 2. ORTEP drawing of the other independent molecule of [Cu(Hchel)(dmp)]. Thermal ellipsoids are shown at 50% probability level.
[Figure 3] Fig. 3. Crystal packing of the title complex, dashed lines indicate hydrogen bonds.
(2,9-Dimethyl-1,10-phenanthroline)(4-hydroxypyridine-2,6- dicarboxylato)copper(II) trihydrate top
Crystal data top
[Cu(C7H3NO5)(C14H12N2)]·3H2OZ = 4
Mr = 506.95F(000) = 1044
Triclinic, P1Dx = 1.634 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0212 (2) ÅCell parameters from 10056 reflections
b = 14.8645 (3) Åθ = 2.3–30.3°
c = 15.4418 (3) ŵ = 1.12 mm−1
α = 91.193 (1)°T = 150 K
β = 106.836 (1)°Block, blue
γ = 109.263 (1)°0.18 × 0.18 × 0.16 mm
V = 2061.05 (7) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		12549 independent reflections
Radiation source: fine-focus sealed tube9400 reflections with I > 2σ(I)
graphiteRint = 0.043
φ and ω scansθmax = 30.7°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→13
Tmin = 0.824, Tmax = 0.842k = −21→21
46562 measured reflectionsl = −22→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0696P)2 + 0.1969P]
where P = (Fo2 + 2Fc2)/3
12549 reflections(Δ/σ)max = 0.002
601 parametersΔρmax = 0.92 e Å−3
0 restraintsΔρmin = −0.87 e Å−3
Crystal data top
[Cu(C7H3NO5)(C14H12N2)]·3H2Oγ = 109.263 (1)°
Mr = 506.95V = 2061.05 (7) Å3
Triclinic, P1Z = 4
a = 10.0212 (2) ÅMo Kα radiation
b = 14.8645 (3) ŵ = 1.12 mm−1
c = 15.4418 (3) ÅT = 150 K
α = 91.193 (1)°0.18 × 0.18 × 0.16 mm
β = 106.836 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		12549 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		9400 reflections with I > 2σ(I)
Tmin = 0.824, Tmax = 0.842Rint = 0.043
46562 measured reflectionsθmax = 30.7°
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.92 e Å−3
S = 1.06Δρmin = −0.87 e Å−3
12549 reflectionsAbsolute structure: ?
601 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Cu10.18000 (3)0.776157 (17)0.315608 (16)0.01236 (7)
Cu20.89377 (3)0.750300 (18)0.759838 (16)0.01373 (7)
O1−0.02604 (16)0.67332 (11)0.27155 (10)0.0178 (3)
O2−0.17402 (17)0.56098 (11)0.15312 (10)0.0217 (3)
O30.15699 (18)0.65953 (12)−0.06028 (10)0.0229 (3)
H3C0.23390.6929−0.07200.034*
O40.51539 (17)0.92317 (11)0.22333 (11)0.0221 (3)
O50.36783 (16)0.88012 (10)0.31126 (9)0.0150 (3)
O61.10226 (17)0.84891 (11)0.79318 (10)0.0186 (3)
O71.27334 (17)0.95980 (12)0.90676 (10)0.0214 (3)
O80.95793 (17)0.90993 (11)1.13195 (10)0.0196 (3)
H8C0.87780.88711.14410.029*
O90.57249 (17)0.62956 (11)0.87302 (10)0.0206 (3)
O100.70852 (16)0.65093 (11)0.77791 (10)0.0169 (3)
N10.17688 (18)0.82702 (12)0.43438 (11)0.0115 (3)
N20.28176 (19)0.68645 (12)0.40714 (11)0.0139 (3)
N30.16794 (19)0.74652 (12)0.19294 (11)0.0128 (3)
N40.75691 (19)0.81640 (12)0.65962 (11)0.0140 (3)
N50.89303 (19)0.68955 (12)0.64437 (11)0.0133 (3)
N60.91937 (19)0.79431 (12)0.88159 (11)0.0125 (3)
C10.3294 (2)0.61610 (15)0.39115 (14)0.0163 (4)
C20.3859 (3)0.56796 (17)0.46299 (15)0.0220 (5)
H20.41530.51600.45000.026*
C30.3985 (3)0.59535 (17)0.55083 (15)0.0220 (5)
H30.43870.56370.59900.026*
C40.3513 (2)0.67093 (15)0.56916 (14)0.0158 (4)
C50.3611 (2)0.70513 (16)0.65927 (14)0.0191 (4)
H50.40160.67640.70990.023*
C60.3133 (2)0.77814 (16)0.67294 (14)0.0174 (4)
H60.32180.80050.73310.021*
C70.2502 (2)0.82174 (15)0.59763 (13)0.0151 (4)
C80.1995 (2)0.89834 (15)0.60858 (14)0.0164 (4)
H80.20800.92410.66760.020*
C90.1379 (2)0.93450 (15)0.53255 (14)0.0164 (4)
H90.10340.98580.53900.020*
C100.1248 (2)0.89678 (14)0.44484 (13)0.0133 (4)
C110.2379 (2)0.78919 (14)0.50869 (13)0.0125 (4)
C120.2918 (2)0.71320 (15)0.49419 (13)0.0137 (4)
C130.0502 (2)0.93156 (15)0.36039 (14)0.0154 (4)
H13A0.10120.93140.31510.023*
H13B0.05450.99700.37550.023*
H13C−0.05410.88900.33540.023*
C140.3228 (3)0.58905 (17)0.29559 (15)0.0211 (5)
H14A0.22230.57750.25420.032*
H14B0.34690.53060.29260.032*
H14C0.39480.64140.27750.032*
C15−0.0619 (2)0.63130 (15)0.19051 (14)0.0153 (4)
C160.0507 (2)0.67360 (15)0.14055 (13)0.0141 (4)
C170.0453 (2)0.64275 (15)0.05485 (14)0.0162 (4)
H17−0.03780.59050.01780.019*
C180.1649 (2)0.68981 (16)0.02292 (14)0.0172 (4)
C190.2855 (2)0.76720 (15)0.07962 (14)0.0162 (4)
H190.36730.80080.05950.019*
C200.2825 (2)0.79327 (14)0.16487 (13)0.0130 (4)
C210.4010 (2)0.87260 (15)0.23753 (14)0.0151 (4)
C220.6861 (2)0.87632 (14)0.66901 (14)0.0137 (4)
C230.6090 (2)0.91006 (15)0.59242 (14)0.0162 (4)
H230.55840.95200.60040.019*
C240.6071 (2)0.88225 (15)0.50639 (14)0.0161 (4)
H240.55640.90550.45490.019*
C250.6811 (2)0.81892 (15)0.49529 (14)0.0145 (4)
C260.6880 (2)0.78837 (15)0.40854 (13)0.0160 (4)
H260.64120.81110.35530.019*
C270.7608 (2)0.72721 (15)0.40165 (13)0.0160 (4)
H270.76550.70830.34380.019*
C280.8305 (2)0.69104 (15)0.48090 (13)0.0143 (4)
C290.9066 (2)0.62694 (15)0.47755 (14)0.0164 (4)
H290.91320.60540.42110.020*
C300.9709 (2)0.59608 (15)0.55649 (14)0.0164 (4)
H301.02180.55270.55450.020*
C310.9624 (2)0.62803 (14)0.64040 (14)0.0147 (4)
C320.8278 (2)0.72104 (14)0.56680 (13)0.0125 (4)
C330.7531 (2)0.78780 (14)0.57459 (13)0.0127 (4)
C341.0325 (3)0.59555 (16)0.72729 (14)0.0188 (4)
H34A1.13030.64400.75880.028*
H34B1.04420.53440.71360.028*
H34C0.96880.58690.76640.028*
C350.6941 (3)0.90849 (16)0.76295 (14)0.0191 (4)
H35A0.65820.85220.79310.029*
H35B0.63180.94800.75970.029*
H35C0.79740.94640.79790.029*
C35A1.1514 (2)0.89664 (15)0.87318 (14)0.0157 (4)
C361.0421 (2)0.86719 (14)0.92753 (13)0.0133 (4)
C371.0587 (2)0.90636 (15)1.01326 (13)0.0146 (4)
H371.14710.95751.04650.018*
C380.9421 (2)0.86912 (15)1.05067 (13)0.0147 (4)
C390.8153 (2)0.79024 (15)1.00122 (14)0.0145 (4)
H390.73630.76241.02560.017*
C400.8096 (2)0.75499 (14)0.91681 (13)0.0128 (4)
C410.6861 (2)0.67159 (15)0.85124 (14)0.0155 (4)
O1S−0.36552 (18)0.52690 (11)0.25879 (11)0.0233 (3)
H1B−0.43250.47490.22900.028*
H1A−0.29500.52590.23910.028*
O2S0.72446 (18)0.85157 (12)1.18104 (11)0.0242 (4)
H2A0.68200.89151.18610.029*
H2B0.67440.79331.18230.029*
O3S0.40048 (19)0.73524 (13)−0.09847 (11)0.0281 (4)
H3B0.45910.7047−0.09710.034*
H3A0.45220.7936−0.07720.034*
O4S0.3462 (3)0.52186 (14)0.02695 (14)0.0551 (7)
H4A0.39050.48140.03460.066*
H4B0.29780.5028−0.02920.066*
O5S0.55325 (19)0.92630 (12)−0.07300 (11)0.0282 (4)
H5B0.60760.9614−0.02270.034*
H5A0.47950.9447−0.09350.034*
O6S0.5503 (2)0.66922 (13)0.16038 (13)0.0351 (4)
H6A0.48960.63460.11110.042*
H6B0.58650.63120.19110.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01313 (13)0.01541 (13)0.00901 (11)0.00463 (10)0.00468 (9)0.00021 (9)
Cu20.01492 (13)0.01556 (13)0.01061 (12)0.00421 (10)0.00533 (10)−0.00019 (9)
O10.0158 (7)0.0226 (8)0.0127 (7)0.0029 (6)0.0059 (6)−0.0018 (6)
O20.0183 (8)0.0235 (8)0.0176 (7)0.0011 (7)0.0048 (6)−0.0016 (6)
O30.0210 (8)0.0347 (10)0.0137 (7)0.0086 (7)0.0080 (6)−0.0042 (6)
O40.0183 (8)0.0214 (8)0.0247 (8)0.0000 (6)0.0123 (7)−0.0027 (6)
O50.0160 (7)0.0162 (7)0.0120 (6)0.0042 (6)0.0051 (6)−0.0003 (5)
O60.0203 (8)0.0212 (8)0.0140 (7)0.0039 (6)0.0093 (6)−0.0007 (6)
O70.0144 (7)0.0267 (9)0.0194 (7)0.0004 (7)0.0081 (6)−0.0014 (6)
O80.0171 (8)0.0261 (8)0.0135 (7)0.0026 (7)0.0081 (6)−0.0056 (6)
O90.0188 (8)0.0188 (8)0.0212 (8)−0.0010 (6)0.0109 (7)−0.0023 (6)
O100.0184 (8)0.0164 (7)0.0143 (7)0.0022 (6)0.0075 (6)−0.0020 (6)
N10.0109 (8)0.0130 (8)0.0103 (7)0.0031 (6)0.0042 (6)0.0006 (6)
N20.0137 (8)0.0163 (8)0.0127 (8)0.0064 (7)0.0043 (7)0.0008 (6)
N30.0140 (8)0.0163 (8)0.0106 (7)0.0070 (7)0.0054 (7)0.0029 (6)
N40.0169 (9)0.0143 (8)0.0107 (7)0.0053 (7)0.0045 (7)0.0009 (6)
N50.0152 (8)0.0143 (8)0.0105 (7)0.0050 (7)0.0046 (7)−0.0008 (6)
N60.0135 (8)0.0137 (8)0.0105 (7)0.0051 (7)0.0037 (7)0.0011 (6)
C10.0146 (10)0.0162 (10)0.0172 (9)0.0052 (8)0.0042 (8)0.0001 (8)
C20.0249 (12)0.0241 (12)0.0224 (11)0.0168 (10)0.0058 (9)0.0033 (9)
C30.0238 (11)0.0256 (12)0.0205 (10)0.0140 (10)0.0062 (9)0.0072 (9)
C40.0130 (10)0.0190 (10)0.0161 (9)0.0066 (8)0.0042 (8)0.0031 (8)
C50.0174 (10)0.0261 (12)0.0144 (9)0.0081 (9)0.0049 (8)0.0069 (8)
C60.0159 (10)0.0233 (11)0.0120 (9)0.0060 (9)0.0040 (8)0.0022 (8)
C70.0139 (9)0.0195 (10)0.0114 (9)0.0046 (8)0.0050 (8)0.0012 (7)
C80.0172 (10)0.0187 (10)0.0136 (9)0.0048 (8)0.0074 (8)−0.0010 (8)
C90.0185 (10)0.0165 (10)0.0163 (9)0.0068 (8)0.0079 (8)0.0001 (8)
C100.0114 (9)0.0151 (10)0.0137 (9)0.0032 (8)0.0064 (8)0.0016 (7)
C110.0110 (9)0.0140 (9)0.0118 (8)0.0034 (7)0.0038 (7)0.0025 (7)
C120.0120 (9)0.0154 (10)0.0135 (9)0.0041 (8)0.0048 (8)0.0007 (7)
C130.0159 (10)0.0172 (10)0.0154 (9)0.0077 (8)0.0062 (8)0.0035 (8)
C140.0252 (12)0.0223 (11)0.0191 (10)0.0126 (10)0.0071 (9)−0.0003 (8)
C150.0146 (10)0.0181 (10)0.0136 (9)0.0062 (8)0.0044 (8)0.0021 (8)
C160.0149 (10)0.0166 (10)0.0122 (9)0.0072 (8)0.0045 (8)0.0010 (7)
C170.0146 (10)0.0184 (10)0.0136 (9)0.0061 (8)0.0015 (8)−0.0015 (8)
C180.0188 (10)0.0261 (11)0.0104 (9)0.0125 (9)0.0048 (8)0.0007 (8)
C190.0161 (10)0.0219 (11)0.0143 (9)0.0093 (9)0.0070 (8)0.0035 (8)
C200.0140 (9)0.0143 (9)0.0119 (9)0.0071 (8)0.0035 (8)0.0022 (7)
C210.0168 (10)0.0156 (10)0.0153 (9)0.0078 (8)0.0065 (8)0.0014 (7)
C220.0129 (9)0.0126 (9)0.0154 (9)0.0037 (8)0.0051 (8)0.0006 (7)
C230.0138 (10)0.0148 (10)0.0202 (10)0.0050 (8)0.0058 (8)0.0009 (8)
C240.0134 (10)0.0155 (10)0.0171 (9)0.0043 (8)0.0023 (8)0.0027 (8)
C250.0137 (9)0.0145 (9)0.0132 (9)0.0027 (8)0.0038 (8)0.0016 (7)
C260.0159 (10)0.0187 (10)0.0109 (9)0.0037 (8)0.0034 (8)0.0028 (7)
C270.0158 (10)0.0175 (10)0.0106 (9)0.0014 (8)0.0033 (8)−0.0007 (7)
C280.0136 (9)0.0141 (9)0.0121 (9)0.0008 (8)0.0042 (8)−0.0018 (7)
C290.0184 (10)0.0168 (10)0.0135 (9)0.0039 (8)0.0075 (8)−0.0021 (7)
C300.0189 (10)0.0165 (10)0.0148 (9)0.0082 (8)0.0047 (8)−0.0021 (8)
C310.0157 (10)0.0130 (9)0.0142 (9)0.0034 (8)0.0050 (8)−0.0005 (7)
C320.0134 (9)0.0125 (9)0.0107 (8)0.0029 (8)0.0044 (7)−0.0007 (7)
C330.0122 (9)0.0125 (9)0.0121 (8)0.0024 (7)0.0041 (7)−0.0004 (7)
C340.0243 (11)0.0219 (11)0.0147 (9)0.0137 (9)0.0059 (9)0.0026 (8)
C350.0225 (11)0.0203 (11)0.0174 (10)0.0103 (9)0.0075 (9)−0.0003 (8)
C35A0.0168 (10)0.0193 (10)0.0133 (9)0.0075 (8)0.0067 (8)0.0013 (8)
C360.0141 (9)0.0149 (9)0.0125 (9)0.0067 (8)0.0049 (8)0.0018 (7)
C370.0130 (9)0.0157 (10)0.0131 (9)0.0040 (8)0.0026 (8)−0.0009 (7)
C380.0164 (10)0.0178 (10)0.0113 (9)0.0075 (8)0.0050 (8)−0.0001 (7)
C390.0137 (9)0.0166 (10)0.0145 (9)0.0047 (8)0.0068 (8)0.0022 (7)
C400.0132 (9)0.0134 (9)0.0121 (9)0.0044 (8)0.0048 (8)0.0013 (7)
C410.0170 (10)0.0136 (9)0.0156 (9)0.0050 (8)0.0050 (8)0.0017 (7)
O1S0.0214 (8)0.0210 (8)0.0231 (8)0.0006 (7)0.0087 (7)−0.0034 (6)
O2S0.0240 (9)0.0206 (8)0.0346 (9)0.0076 (7)0.0189 (8)0.0060 (7)
O3S0.0223 (9)0.0335 (10)0.0307 (9)0.0096 (8)0.0120 (7)−0.0012 (7)
O4S0.0751 (17)0.0324 (11)0.0303 (11)0.0164 (11)−0.0206 (11)−0.0035 (9)
O5S0.0257 (9)0.0347 (10)0.0237 (8)0.0149 (8)0.0026 (7)−0.0078 (7)
O6S0.0297 (10)0.0243 (9)0.0404 (11)0.0075 (8)−0.0028 (8)0.0039 (8)
Geometric parameters (Å, °) top
Cu1—N31.8959 (16)C14—H14A0.9800
Cu1—N11.9818 (16)C14—H14B0.9800
Cu1—O52.0234 (15)C14—H14C0.9800
Cu1—O12.0306 (15)C15—C161.523 (3)
Cu1—N22.2263 (17)C16—C171.372 (3)
Cu2—N61.8940 (16)C17—C181.404 (3)
Cu2—N51.9787 (16)C17—H170.9500
Cu2—O62.0257 (16)C18—C191.407 (3)
Cu2—O102.0528 (15)C19—C201.376 (3)
Cu2—N42.2281 (17)C19—H190.9500
O1—C151.282 (2)C20—C211.519 (3)
O2—C151.230 (3)C22—C231.414 (3)
O3—C181.324 (2)C22—C351.489 (3)
O3—H3C0.8400C23—C241.376 (3)
O4—C211.229 (3)C23—H230.9500
O5—C211.287 (2)C24—C251.412 (3)
O6—C35A1.286 (2)C24—H240.9500
O7—C35A1.224 (3)C25—C331.402 (3)
O8—C381.326 (2)C25—C261.433 (3)
O8—H8C0.8400C26—C271.360 (3)
O9—C411.250 (3)C26—H260.9500
O10—C411.267 (2)C27—C281.433 (3)
N1—C101.331 (3)C27—H270.9500
N1—C111.362 (2)C28—C321.401 (3)
N2—C11.330 (3)C28—C291.412 (3)
N2—C121.360 (3)C29—C301.369 (3)
N3—C201.328 (3)C29—H290.9500
N3—C161.335 (3)C30—C311.406 (3)
N4—C221.338 (3)C30—H300.9500
N4—C331.358 (2)C31—C341.494 (3)
N5—C311.328 (3)C32—C331.448 (3)
N5—C321.361 (2)C34—H34A0.9800
N6—C361.332 (3)C34—H34B0.9800
N6—C401.336 (3)C34—H34C0.9800
C1—C21.414 (3)C35—H35A0.9800
C1—C141.498 (3)C35—H35B0.9800
C2—C31.366 (3)C35—H35C0.9800
C2—H20.9500C35A—C361.525 (3)
C3—C41.407 (3)C36—C371.377 (3)
C3—H30.9500C37—C381.408 (3)
C4—C121.403 (3)C37—H370.9500
C4—C51.436 (3)C38—C391.411 (3)
C5—C61.358 (3)C39—C401.373 (3)
C5—H50.9500C39—H390.9500
C6—C71.431 (3)C40—C411.517 (3)
C6—H60.9500O1S—H1B0.8500
C7—C111.404 (3)O1S—H1A0.8500
C7—C81.417 (3)O2S—H2A0.8500
C8—C91.369 (3)O2S—H2B0.8500
C8—H80.9500O3S—H3B0.8500
C9—C101.408 (3)O3S—H3A0.8500
C9—H90.9500O4S—H4A0.8500
C10—C131.499 (3)O4S—H4B0.8500
C11—C121.442 (3)O5S—H5B0.8501
C13—H13A0.9800O5S—H5A0.8501
C13—H13B0.9800O6S—H6A0.8500
C13—H13C0.9800O6S—H6B0.8501
N3—Cu1—N1168.68 (7)O1—C15—C16114.46 (18)
N3—Cu1—O580.32 (7)N3—C16—C17120.63 (19)
N1—Cu1—O597.54 (6)N3—C16—C15111.38 (17)
N3—Cu1—O180.62 (7)C17—C16—C15127.92 (19)
N1—Cu1—O199.73 (6)C16—C17—C18118.77 (19)
O5—Cu1—O1159.59 (6)C16—C17—H17120.6
N3—Cu1—N2111.53 (7)C18—C17—H17120.6
N1—Cu1—N279.77 (6)O3—C18—C17117.9 (2)
O5—Cu1—N299.28 (6)O3—C18—C19123.2 (2)
O1—Cu1—N294.45 (6)C17—C18—C19118.94 (19)
N6—Cu2—N5168.36 (7)C20—C19—C18118.6 (2)
N6—Cu2—O680.28 (7)C20—C19—H19120.7
N5—Cu2—O696.98 (7)C18—C19—H19120.7
N6—Cu2—O1080.35 (7)N3—C20—C19120.70 (19)
N5—Cu2—O10100.13 (7)N3—C20—C21111.76 (17)
O6—Cu2—O10158.49 (6)C19—C20—C21127.53 (19)
N6—Cu2—N4111.71 (7)O4—C21—O5125.7 (2)
N5—Cu2—N479.92 (7)O4—C21—C20120.64 (18)
O6—Cu2—N4103.56 (6)O5—C21—C20113.69 (18)
O10—Cu2—N492.23 (6)N4—C22—C23121.14 (18)
C15—O1—Cu1114.37 (13)N4—C22—C35117.98 (18)
C18—O3—H3C109.5C23—C22—C35120.86 (18)
C21—O5—Cu1114.81 (13)C24—C23—C22120.11 (19)
C35A—O6—Cu2115.27 (13)C24—C23—H23119.9
C38—O8—H8C109.5C22—C23—H23119.9
C41—O10—Cu2113.04 (13)C23—C24—C25119.45 (19)
C10—N1—C11119.81 (17)C23—C24—H24120.3
C10—N1—Cu1123.96 (13)C25—C24—H24120.3
C11—N1—Cu1116.18 (13)C33—C25—C24116.83 (18)
C1—N2—C12118.95 (17)C33—C25—C26120.08 (18)
C1—N2—Cu1132.37 (14)C24—C25—C26123.07 (18)
C12—N2—Cu1108.69 (13)C27—C26—C25120.69 (19)
C20—N3—C16122.35 (18)C27—C26—H26119.7
C20—N3—Cu1118.70 (14)C25—C26—H26119.7
C16—N3—Cu1118.67 (14)C26—C27—C28120.59 (19)
C22—N4—C33118.74 (17)C26—C27—H27119.7
C22—N4—Cu2132.73 (14)C28—C27—H27119.7
C33—N4—Cu2108.52 (13)C32—C28—C29117.11 (18)
C31—N5—C32120.07 (17)C32—C28—C27119.93 (18)
C31—N5—Cu2123.70 (14)C29—C28—C27122.94 (18)
C32—N5—Cu2115.96 (13)C30—C29—C28119.35 (19)
C36—N6—C40121.98 (17)C30—C29—H29120.3
C36—N6—Cu2119.09 (14)C28—C29—H29120.3
C40—N6—Cu2118.81 (14)C29—C30—C31120.65 (19)
N2—C1—C2120.68 (19)C29—C30—H30119.7
N2—C1—C14118.75 (18)C31—C30—H30119.7
C2—C1—C14120.56 (19)N5—C31—C30120.39 (18)
C3—C2—C1120.7 (2)N5—C31—C34118.18 (18)
C3—C2—H2119.6C30—C31—C34121.43 (18)
C1—C2—H2119.6N5—C32—C28122.42 (18)
C2—C3—C4119.2 (2)N5—C32—C33118.02 (17)
C2—C3—H3120.4C28—C32—C33119.56 (18)
C4—C3—H3120.4N4—C33—C25123.71 (18)
C12—C4—C3116.91 (19)N4—C33—C32117.22 (17)
C12—C4—C5119.85 (18)C25—C33—C32119.07 (17)
C3—C4—C5123.25 (19)C31—C34—H34A109.5
C6—C5—C4120.74 (19)C31—C34—H34B109.5
C6—C5—H5119.6H34A—C34—H34B109.5
C4—C5—H5119.6C31—C34—H34C109.5
C5—C6—C7120.63 (19)H34A—C34—H34C109.5
C5—C6—H6119.7H34B—C34—H34C109.5
C7—C6—H6119.7C22—C35—H35A109.5
C11—C7—C8117.47 (18)C22—C35—H35B109.5
C11—C7—C6119.89 (18)H35A—C35—H35B109.5
C8—C7—C6122.64 (18)C22—C35—H35C109.5
C9—C8—C7118.74 (18)H35A—C35—H35C109.5
C9—C8—H8120.6H35B—C35—H35C109.5
C7—C8—H8120.6O7—C35A—O6126.1 (2)
C8—C9—C10121.01 (19)O7—C35A—C36120.32 (18)
C8—C9—H9119.5O6—C35A—C36113.61 (18)
C10—C9—H9119.5N6—C36—C37120.64 (19)
N1—C10—C9120.49 (18)N6—C36—C35A111.47 (17)
N1—C10—C13117.63 (17)C37—C36—C35A127.89 (19)
C9—C10—C13121.87 (18)C36—C37—C38118.71 (19)
N1—C11—C7122.41 (18)C36—C37—H37120.6
N1—C11—C12117.98 (17)C38—C37—H37120.6
C7—C11—C12119.60 (18)O8—C38—C37117.86 (19)
N2—C12—C4123.42 (18)O8—C38—C39122.96 (19)
N2—C12—C11117.32 (17)C37—C38—C39119.18 (18)
C4—C12—C11119.27 (18)C40—C39—C38117.95 (19)
C10—C13—H13A109.5C40—C39—H39121.0
C10—C13—H13B109.5C38—C39—H39121.0
H13A—C13—H13B109.5N6—C40—C39121.46 (19)
C10—C13—H13C109.5N6—C40—C41110.82 (17)
H13A—C13—H13C109.5C39—C40—C41127.72 (19)
H13B—C13—H13C109.5O9—C41—O10125.6 (2)
C1—C14—H14A109.5O9—C41—C40118.47 (18)
C1—C14—H14B109.5O10—C41—C40115.93 (18)
H14A—C14—H14B109.5H1B—O1S—H1A99.2
C1—C14—H14C109.5H2A—O2S—H2B115.2
H14A—C14—H14C109.5H3B—O3S—H3A108.5
H14B—C14—H14C109.5H4A—O4S—H4B96.6
O2—C15—O1125.8 (2)H5B—O5S—H5A107.1
O2—C15—C16119.72 (18)H6A—O6S—H6B104.7
N3—Cu1—O1—C156.39 (14)N1—C11—C12—N21.9 (3)
N1—Cu1—O1—C15174.92 (14)C7—C11—C12—N2−177.88 (18)
O5—Cu1—O1—C1527.6 (3)N1—C11—C12—C4−178.17 (18)
N2—Cu1—O1—C15−104.72 (15)C7—C11—C12—C42.0 (3)
N3—Cu1—O5—C21−7.58 (14)Cu1—O1—C15—O2172.45 (17)
N1—Cu1—O5—C21−176.34 (14)Cu1—O1—C15—C16−5.7 (2)
O1—Cu1—O5—C21−28.8 (3)C20—N3—C16—C171.1 (3)
N2—Cu1—O5—C21102.87 (14)Cu1—N3—C16—C17−172.68 (15)
N6—Cu2—O6—C35A−3.25 (15)C20—N3—C16—C15178.32 (17)
N5—Cu2—O6—C35A−171.81 (15)Cu1—N3—C16—C154.5 (2)
O10—Cu2—O6—C35A−29.3 (3)O2—C15—C16—N3−177.16 (18)
N4—Cu2—O6—C35A106.93 (15)O1—C15—C16—N31.1 (3)
N6—Cu2—O10—C419.37 (14)O2—C15—C16—C17−0.2 (3)
N5—Cu2—O10—C41177.56 (14)O1—C15—C16—C17178.1 (2)
O6—Cu2—O10—C4135.4 (2)N3—C16—C17—C18−0.5 (3)
N4—Cu2—O10—C41−102.29 (14)C15—C16—C17—C18−177.25 (19)
N3—Cu1—N1—C103.2 (5)C16—C17—C18—O3−179.41 (19)
O5—Cu1—N1—C1081.50 (16)C16—C17—C18—C19−0.3 (3)
O1—Cu1—N1—C10−87.56 (16)O3—C18—C19—C20179.71 (19)
N2—Cu1—N1—C10179.63 (17)C17—C18—C19—C200.7 (3)
N3—Cu1—N1—C11−174.1 (3)C16—N3—C20—C19−0.7 (3)
O5—Cu1—N1—C11−95.83 (14)Cu1—N3—C20—C19173.04 (15)
O1—Cu1—N1—C1195.11 (14)C16—N3—C20—C21−179.77 (17)
N2—Cu1—N1—C112.30 (14)Cu1—N3—C20—C21−6.0 (2)
N3—Cu1—N2—C1−2.5 (2)C18—C19—C20—N3−0.2 (3)
N1—Cu1—N2—C1178.3 (2)C18—C19—C20—C21178.70 (19)
O5—Cu1—N2—C1−85.68 (19)Cu1—O5—C21—O4−174.05 (17)
O1—Cu1—N2—C179.16 (19)Cu1—O5—C21—C206.4 (2)
N3—Cu1—N2—C12178.01 (13)N3—C20—C21—O4179.77 (18)
N1—Cu1—N2—C12−1.23 (13)C19—C20—C21—O40.8 (3)
O5—Cu1—N2—C1294.83 (14)N3—C20—C21—O5−0.7 (2)
O1—Cu1—N2—C12−100.33 (14)C19—C20—C21—O5−179.62 (19)
N1—Cu1—N3—C2087.4 (4)C33—N4—C22—C23−0.3 (3)
O5—Cu1—N3—C207.40 (14)Cu2—N4—C22—C23178.15 (15)
O1—Cu1—N3—C20−179.94 (16)C33—N4—C22—C35−178.77 (18)
N2—Cu1—N3—C20−88.83 (15)Cu2—N4—C22—C35−0.3 (3)
N1—Cu1—N3—C16−98.6 (4)N4—C22—C23—C24−0.7 (3)
O5—Cu1—N3—C16−178.60 (16)C35—C22—C23—C24177.7 (2)
O1—Cu1—N3—C16−5.94 (15)C22—C23—C24—C250.8 (3)
N2—Cu1—N3—C1685.17 (16)C23—C24—C25—C330.1 (3)
N6—Cu2—N4—C22−3.4 (2)C23—C24—C25—C26−178.3 (2)
N5—Cu2—N4—C22177.0 (2)C33—C25—C26—C271.7 (3)
O6—Cu2—N4—C22−88.16 (19)C24—C25—C26—C27180.0 (2)
O10—Cu2—N4—C2277.12 (19)C25—C26—C27—C280.8 (3)
N6—Cu2—N4—C33175.18 (13)C26—C27—C28—C32−2.0 (3)
N5—Cu2—N4—C33−4.43 (13)C26—C27—C28—C29179.6 (2)
O6—Cu2—N4—C3390.39 (14)C32—C28—C29—C301.2 (3)
O10—Cu2—N4—C33−104.33 (13)C27—C28—C29—C30179.7 (2)
N6—Cu2—N5—C311.4 (5)C28—C29—C30—C31−0.4 (3)
O6—Cu2—N5—C3176.98 (17)C32—N5—C31—C300.9 (3)
O10—Cu2—N5—C31−89.94 (17)Cu2—N5—C31—C30−172.86 (15)
N4—Cu2—N5—C31179.58 (18)C32—N5—C31—C34179.94 (19)
N6—Cu2—N5—C32−172.7 (3)Cu2—N5—C31—C346.1 (3)
O6—Cu2—N5—C32−97.06 (15)C29—C30—C31—N5−0.7 (3)
O10—Cu2—N5—C3296.02 (15)C29—C30—C31—C34−179.7 (2)
N4—Cu2—N5—C325.54 (14)C31—N5—C32—C28−0.1 (3)
N5—Cu2—N6—C3682.3 (4)Cu2—N5—C32—C28174.19 (15)
O6—Cu2—N6—C365.06 (14)C31—N5—C32—C33179.80 (19)
O10—Cu2—N6—C36175.67 (16)Cu2—N5—C32—C33−5.9 (2)
N4—Cu2—N6—C36−95.77 (15)C29—C28—C32—N5−1.0 (3)
N5—Cu2—N6—C40−101.6 (4)C27—C28—C32—N5−179.53 (18)
O6—Cu2—N6—C40−178.89 (16)C29—C28—C32—C33179.15 (19)
O10—Cu2—N6—C40−8.27 (14)C27—C28—C32—C330.6 (3)
N4—Cu2—N6—C4080.28 (16)C22—N4—C33—C251.2 (3)
C12—N2—C1—C21.7 (3)Cu2—N4—C33—C25−177.56 (16)
Cu1—N2—C1—C2−177.74 (16)C22—N4—C33—C32−178.47 (18)
C12—N2—C1—C14−178.02 (19)Cu2—N4—C33—C322.7 (2)
Cu1—N2—C1—C142.5 (3)C24—C25—C33—N4−1.1 (3)
N2—C1—C2—C3−2.8 (3)C26—C25—C33—N4177.31 (19)
C14—C1—C2—C3176.9 (2)C24—C25—C33—C32178.58 (19)
C1—C2—C3—C41.5 (4)C26—C25—C33—C32−3.0 (3)
C2—C3—C4—C120.7 (3)N5—C32—C33—N41.7 (3)
C2—C3—C4—C5−179.6 (2)C28—C32—C33—N4−178.42 (18)
C12—C4—C5—C60.0 (3)N5—C32—C33—C25−178.02 (18)
C3—C4—C5—C6−179.7 (2)C28—C32—C33—C251.9 (3)
C4—C5—C6—C70.8 (3)Cu2—O6—C35A—O7−179.46 (18)
C5—C6—C7—C11−0.2 (3)Cu2—O6—C35A—C361.2 (2)
C5—C6—C7—C8−179.7 (2)C40—N6—C36—C37−1.5 (3)
C11—C7—C8—C91.8 (3)Cu2—N6—C36—C37174.45 (15)
C6—C7—C8—C9−178.7 (2)C40—N6—C36—C35A178.38 (17)
C7—C8—C9—C100.0 (3)Cu2—N6—C36—C35A−5.7 (2)
C11—N1—C10—C92.6 (3)O7—C35A—C36—N6−176.72 (19)
Cu1—N1—C10—C9−174.66 (15)O6—C35A—C36—N62.7 (2)
C11—N1—C10—C13−176.24 (18)O7—C35A—C36—C373.1 (3)
Cu1—N1—C10—C136.5 (3)O6—C35A—C36—C37−177.47 (19)
C8—C9—C10—N1−2.2 (3)N6—C36—C37—C38−1.2 (3)
C8—C9—C10—C13176.5 (2)C35A—C36—C37—C38178.94 (19)
C10—N1—C11—C7−0.7 (3)C36—C37—C38—O8−177.71 (18)
Cu1—N1—C11—C7176.72 (15)C36—C37—C38—C392.9 (3)
C10—N1—C11—C12179.48 (18)O8—C38—C39—C40178.69 (19)
Cu1—N1—C11—C12−3.1 (2)C37—C38—C39—C40−1.9 (3)
C8—C7—C11—N1−1.5 (3)C36—N6—C40—C392.5 (3)
C6—C7—C11—N1178.99 (19)Cu2—N6—C40—C39−173.44 (15)
C8—C7—C11—C12178.31 (19)C36—N6—C40—C41−178.16 (17)
C6—C7—C11—C12−1.2 (3)Cu2—N6—C40—C415.9 (2)
C1—N2—C12—C40.6 (3)C38—C39—C40—N6−0.7 (3)
Cu1—N2—C12—C4−179.87 (16)C38—C39—C40—C41−179.95 (19)
C1—N2—C12—C11−179.53 (18)Cu2—O10—C41—O9171.00 (17)
Cu1—N2—C12—C110.0 (2)Cu2—O10—C41—C40−8.8 (2)
C3—C4—C12—N2−1.8 (3)N6—C40—C41—O9−177.29 (18)
C5—C4—C12—N2178.5 (2)C39—C40—C41—O92.0 (3)
C3—C4—C12—C11178.3 (2)N6—C40—C41—O102.5 (3)
C5—C4—C12—C11−1.4 (3)C39—C40—C41—O10−178.16 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3C···O3S0.841.752.572 (2)166
O8—H8C···O2S0.841.722.553 (2)173
O1S—H1B···O9i0.852.012.833 (2)163
O1S—H1A···O20.852.012.794 (2)153
O2S—H2A···O4ii0.852.102.861 (2)149
O2S—H2A···O7iii0.852.643.136 (2)118
O2S—H2B···O6Sii0.851.812.649 (2)168
O3S—H3B···O9iv0.851.972.798 (2)166
O3S—H3A···O5S0.851.892.702 (2)160
O4S—H4A···O9v0.852.262.957 (3)140
O4S—H4B···O2vi0.851.972.811 (2)171
O5S—H5B···O7vii0.851.942.787 (2)178
O5S—H5A···O7viii0.852.152.938 (2)154
O6S—H6A···O4S0.851.952.764 (3)160
O6S—H6B···O1Six0.852.002.840 (2)170
C13—H13B···Cg1x0.982.763.372 (2)121
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+2, −y+2, −z+2; (iv) x, y, z−1; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z; (vii) −x+2, −y+2, −z+1; (viii) x−1, y, z−1; (ix) x+1, y, z; (x) −x+1, −y+2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3C···O3S0.841.752.572 (2)166
O8—H8C···O2S0.841.722.553 (2)173
O1S—H1B···O9i0.852.012.833 (2)163
O1S—H1A···O20.852.012.794 (2)153
O2S—H2A···O4ii0.852.102.861 (2)149
O2S—H2A···O7iii0.852.643.136 (2)118
O2S—H2B···O6Sii0.851.812.649 (2)168
O3S—H3B···O9iv0.851.972.798 (2)166
O3S—H3A···O5S0.851.892.702 (2)160
O4S—H4A···O9v0.852.262.957 (3)140
O4S—H4B···O2vi0.851.972.811 (2)171
O5S—H5B···O7vii0.851.942.787 (2)178
O5S—H5A···O7viii0.852.152.938 (2)154
O6S—H6A···O4S0.851.952.764 (3)160
O6S—H6B···O1Six0.852.002.840 (2)170
C13—H13B···Cg1x0.982.763.372 (2)121
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+2, −y+2, −z+2; (iv) x, y, z−1; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z; (vii) −x+2, −y+2, −z+1; (viii) x−1, y, z−1; (ix) x+1, y, z; (x) −x+1, −y+2, −z+1.
Acknowledgements top

The authors are grateful to Ilam University for financial support.

references
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