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Acta Cryst. (2007). E63, m2120-m2121    [ doi:10.1107/S1600536807032916 ]

[[mu]2-N,N'-Bis(2-oxy-3-ethoxybenzylidene)propane-1,2-diamine](methanol)trinitratocopper(II)lutetium(III)

Y. Sui, R.-H. Hu, J.-L. Peng and S. W. Ng

Abstract top

The Cu atom in the title compound (systematic name: {6,6'-diethoxy-2,2'-[propane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1[kappa]4O1,O1',O6,O6':2[kappa]4O1,N,N',O1'}(methanol-2[kappa]O)trinitrato-1[kappa]6O,O'-copper(II)lutetium(III)), [CuLu(C21H22N2O4)(CH4O)(NO3)3] is N,N',O,O' chelated by the deprotonated Schiff base, the four chelating atoms forming a square plane above which lies the methanol molecule. The [Cu(C21H24N2O4)(CH4O)] unit uses the two ethoxy and two hydroxy O atoms to chelate the [Lu(NO3)3] unit. The CuII atom exists in a square-pyramidal geometry and the LuIII atom in a bicapped square-antiprismatic geometry. Molecules are linked into a chain along the b axis by O-H...O hydrogen bonds. Two CH2 groups of the C2N2Cu ring and the H atoms of the attached methyl group are disordered equally over two positions.

Comment top

3-Alkoxysalicylaldehyde condenses with ethylenediamine and related diamines to form a class of Schiff bases that react with divalent transition-metal salts to afford another class of compounds that react with lanthanum(III) salts to yield bimetallic compounds. Bis(2-oxy-3-methoxybenzylidene)ethylenediamine)(acetone)tris(nitrato)-copper- neodymium (Elmali et al., 2004), bis(2-oxy-3-methoxybenzylidene)ethylenediamine)(acetone)tris(nitrato)-copper- dysprosium (Elmali et al., 2005) and (1,2-cyclohexane)bis(3-ethoxysalicylideneaminato)aquatris(nitrato)\ coppergadolinium (Koner et al., 2005) represent the copper compounds that are coordinated to lanthanum trinitrate. Their copper atoms are chelated by the deprotonated Schiff bases but the geometry is a square-pyramid owing to the coordinated solvent molecules. On the other hand, the lanthanum atom is chelated by three nitrate groups, so a ten-coordinate geometry results from the involvement of the four oxygen atoms of the copper-Schiff base portion of the bimetallic molecule. The title compound (Fig. 1) has a similar bonding mode; the lutetium atom shows bicapped square-antiprismatic coordination.

Related literature top

See Elmali & Elerman (2004) for bis(2-oxy-3-methoxybenzylidene)ethylenediamine)(acetone)tris(nitrato)copperneodymium, Elmali & Elerman (2005) for bis(2-oxy-3-methoxybenzylidene)ethylenediamine)(acetone)tris(nitrato)copperdysprosium and Koner et al. (2005) for (1,2-cyclohexane)bis(3-ethoxysalicylideneaminato)aquatris(nitrato)coppergadolinium.

Experimental top

The Schiff base used to make the title compound was synthesized by the condensation of 3-ethoxysalicylaldehyde and 1,2- diaminopropane in a 2:1 molar ratio. Copper diacetate monohydrate (0.17 g, 1 mmol) and the ligand (0.37 g, 1 mmol) were heated in methanol (50 ml) for 3 h. Lutetium nitrate hexahydrate (0.47 g, 1 mmol) was added and the mixture was heated for another 3 h. Cooling the solution gave a precipitate, which was collected and washed with diethyl ether. Crystals were obtained upon recrystallization from methanol.

Refinement top

The part of the Schiff base that is made up of the C10 and C11 atoms (that belong to the cyclic system) is disordered over two positions; the occupancies of each set of atoms was arbitrarily fixed as 0.5. The displacement parameters of primed atoms were set to those of the unprimed ones. The C10—C11 and C11—C12 bond lengths were restrained to 1.50 (1) Å and the C10···C12 distance to 2.45 (1) Å. The displacement parameters of C10, C11 and C12 were restrained to approximate isotropic behaviour. The carbon- and oxygen-bound H atoms were positioned geometrically (C–H = 0.93–0.97 Å and O—H = 0.82 Å), and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C,O). The final difference Fourier map had a large peak at 0.5 Å from H12D and a deep hole at 0.5 Å from Lu1.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot of [CuLu(C21H22N2O4)(CH4O)(NO3)3]; ellipsoids are drawn at the 30% probabilty level, and H atoms are shown as spheres of arbitrary radius. Only one disorder component is shown.
[µ2-N,N'-Bis(2-oxy-3-ethoxybenzylidene)ethylene-1,2-diamine] (methanol)tris(nitrato)copper(II)lutetium(III) top
Crystal data top
[CuLu(C21H22N2O4)(CH4O)(NO3)3]F(000) = 1628
Mr = 825.00Dx = 1.865 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4544 reflections
a = 9.1795 (5) Åθ = 2.4–22.2°
b = 20.407 (1) ŵ = 4.14 mm−1
c = 15.7058 (9) ÅT = 295 K
β = 93.126 (1)°Block, red
V = 2937.7 (3) Å30.20 × 0.09 × 0.08 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer		6636 independent reflections
Radiation source: fine-focus sealed tube3788 reflections with I > 2σ(I)
graphiteRint = 0.049
φ and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.183, Tmax = 0.733k = −26→26
21167 measured reflectionsl = −20→20
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1059P)2]
where P = (Fo2 + 2Fc2)/3
6636 reflections(Δ/σ)max = 0.001
394 parametersΔρmax = 1.20 e Å−3
10 restraintsΔρmin = −1.29 e Å−3
Crystal data top
[CuLu(C21H22N2O4)(CH4O)(NO3)3]V = 2937.7 (3) Å3
Mr = 825.00Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.1795 (5) ŵ = 4.14 mm−1
b = 20.407 (1) ÅT = 295 K
c = 15.7058 (9) Å0.20 × 0.09 × 0.08 mm
β = 93.126 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer		6636 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3788 reflections with I > 2σ(I)
Tmin = 0.183, Tmax = 0.733Rint = 0.049
21167 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.196Δρmax = 1.20 e Å−3
S = 1.07Δρmin = −1.29 e Å−3
6636 reflectionsAbsolute structure: ?
394 parametersFlack parameter: ?
10 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Lu10.36449 (5)0.34232 (2)0.25150 (3)0.05488 (19)
Cu10.32833 (12)0.50585 (5)0.30039 (7)0.0460 (3)
O10.1485 (8)0.3477 (3)0.1360 (4)0.0525 (16)
O20.2284 (7)0.4406 (3)0.2367 (4)0.0550 (16)
O30.4753 (7)0.4397 (3)0.3108 (4)0.0519 (16)
O40.6441 (7)0.3413 (3)0.2989 (4)0.0489 (15)
O50.4254 (11)0.5592 (4)0.1848 (5)0.101 (3)
H5O0.48650.58750.19690.122*
O60.1569 (10)0.3251 (5)0.3439 (6)0.097 (3)
O70.3518 (12)0.3407 (5)0.4097 (5)0.099 (3)
O80.1587 (12)0.3342 (4)0.4790 (6)0.093 (3)
O90.4776 (8)0.3859 (4)0.1229 (5)0.067 (2)
O100.4809 (9)0.2812 (4)0.1396 (5)0.071 (2)
O110.5937 (12)0.3224 (5)0.0349 (6)0.104 (3)
O120.2362 (8)0.2317 (3)0.2230 (6)0.075 (2)
O130.4277 (8)0.2285 (3)0.3023 (5)0.067 (2)
O140.3179 (10)0.1381 (3)0.2648 (6)0.086 (3)
N10.1675 (10)0.5659 (3)0.3038 (6)0.064 (2)
N20.4260 (9)0.5652 (3)0.3773 (5)0.053 (2)
N30.2196 (11)0.3338 (4)0.4138 (6)0.056 (2)
N40.5218 (12)0.3308 (5)0.0953 (7)0.070 (3)
N50.3281 (10)0.1984 (4)0.2624 (5)0.055 (2)
C10.1685 (19)0.3436 (7)−0.0203 (8)0.107 (5)
H1A0.15140.3160−0.06930.160*
H1B0.26870.3574−0.01670.160*
H1C0.10620.3813−0.02530.160*
C20.1348 (14)0.3045 (5)0.0622 (6)0.069 (3)
H2A0.03670.28680.05650.082*
H2B0.20250.26810.06980.082*
C30.0473 (10)0.3983 (4)0.1446 (6)0.050 (2)
C4−0.0902 (14)0.3990 (6)0.1026 (7)0.081 (4)
H4−0.11960.36590.06470.097*
C5−0.1824 (13)0.4515 (7)0.1197 (8)0.086 (4)
H5−0.27740.45210.09590.103*
C6−0.1351 (12)0.5010 (5)0.1702 (8)0.070 (3)
H6−0.19700.53630.17810.084*
C70.0070 (10)0.5015 (5)0.2122 (7)0.056 (2)
C80.0955 (9)0.4482 (4)0.1980 (6)0.048 (2)
C90.0390 (13)0.5572 (5)0.2657 (7)0.063 (3)
H9−0.03380.58790.27350.076*
C100.2161 (17)0.6300 (6)0.3366 (12)0.053 (4)0.50
H100.26330.65370.29130.063*0.50
C10'0.187 (2)0.6104 (6)0.3762 (10)0.053 (4)0.50
H10'0.16070.58650.42730.063*0.50
C110.1109 (15)0.6748 (6)0.3762 (10)0.108 (5)
H11A0.16260.71160.40110.163*0.50
H11B0.06220.65170.41970.163*0.50
H11C0.04020.68990.33340.163*0.50
H11D0.00740.66770.37270.163*0.50
H11E0.13790.69850.42750.163*0.50
H11F0.13810.69960.32770.163*0.50
C120.328 (3)0.6153 (14)0.4072 (18)0.096 (8)0.50
H12A0.38240.65470.42260.115*0.50
H12B0.28050.59980.45700.115*0.50
C12'0.347 (2)0.6264 (10)0.386 (3)0.096 (8)0.50
H12C0.37280.65750.34290.115*0.50
H12D0.36960.64560.44190.115*0.50
C130.5558 (15)0.5608 (5)0.4052 (7)0.069 (3)
H130.59250.59510.43900.083*
C140.6568 (12)0.5056 (4)0.3894 (6)0.053 (2)
C150.7976 (13)0.5104 (5)0.4195 (6)0.068 (3)
H150.82830.54770.44940.081*
C160.8962 (11)0.4607 (5)0.4065 (6)0.057 (2)
H160.99390.46590.42420.068*
C170.8500 (11)0.4039 (5)0.3676 (6)0.058 (3)
H170.91610.37010.35970.070*
C180.7030 (10)0.3963 (4)0.3395 (6)0.046 (2)
C190.6058 (10)0.4479 (4)0.3458 (5)0.046 (2)
C200.7437 (10)0.2855 (5)0.2863 (7)0.062 (3)
H20A0.83540.30190.26700.075*
H20B0.70110.25700.24220.075*
C210.7735 (12)0.2457 (6)0.3676 (8)0.077 (3)
H21A0.77090.19980.35410.115*
H21B0.70040.25530.40720.115*
H21C0.86800.25690.39260.115*
C220.3956 (19)0.5501 (8)0.1039 (9)0.114 (5)
H22A0.47550.56540.07230.171*
H22B0.30880.57390.08650.171*
H22C0.38050.50420.09310.171*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Lu10.0553 (3)0.0411 (3)0.0676 (3)0.00042 (19)−0.0023 (2)−0.0050 (2)
Cu10.0493 (7)0.0293 (5)0.0591 (7)0.0017 (5)0.0012 (5)−0.0057 (5)
O10.057 (4)0.041 (4)0.058 (4)0.000 (3)−0.010 (3)−0.003 (3)
O20.054 (4)0.036 (3)0.074 (4)0.012 (3)−0.006 (3)−0.009 (3)
O30.047 (4)0.036 (3)0.070 (4)0.008 (3)−0.018 (3)−0.012 (3)
O40.047 (4)0.034 (3)0.065 (4)−0.006 (3)0.001 (3)−0.011 (3)
O50.135 (9)0.086 (6)0.084 (6)−0.053 (6)0.017 (6)0.002 (5)
O60.074 (6)0.145 (9)0.072 (6)0.021 (6)0.019 (5)0.023 (5)
O70.101 (8)0.132 (9)0.062 (5)−0.032 (6)−0.010 (5)−0.003 (5)
O80.138 (9)0.076 (6)0.070 (6)−0.008 (5)0.040 (6)0.007 (4)
O90.066 (5)0.063 (5)0.074 (5)−0.008 (4)0.009 (4)0.015 (4)
O100.083 (6)0.060 (5)0.071 (5)0.005 (4)0.012 (4)−0.019 (4)
O110.119 (8)0.114 (7)0.085 (6)−0.026 (6)0.061 (6)−0.014 (5)
O120.058 (5)0.046 (4)0.119 (6)−0.013 (4)−0.023 (4)0.011 (4)
O130.057 (5)0.045 (4)0.096 (5)−0.009 (3)−0.018 (4)0.011 (4)
O140.101 (6)0.031 (4)0.127 (7)−0.013 (4)0.006 (5)−0.014 (4)
N10.064 (6)0.035 (4)0.092 (6)0.016 (4)−0.007 (5)−0.004 (4)
N20.061 (6)0.031 (4)0.067 (5)0.003 (4)−0.006 (4)−0.008 (4)
N30.069 (7)0.041 (5)0.060 (6)−0.002 (4)0.015 (5)−0.010 (4)
N40.072 (7)0.066 (7)0.071 (6)−0.020 (5)−0.005 (5)−0.001 (5)
N50.070 (6)0.029 (4)0.068 (5)0.000 (4)0.023 (5)−0.003 (4)
C10.124 (14)0.143 (14)0.054 (7)0.011 (10)0.007 (8)0.003 (8)
C20.086 (8)0.054 (6)0.064 (7)−0.005 (6)−0.016 (6)−0.006 (5)
C30.046 (6)0.044 (5)0.058 (6)0.002 (4)−0.005 (4)0.009 (4)
C40.101 (10)0.066 (8)0.071 (8)0.012 (7)−0.027 (7)0.000 (6)
C50.054 (7)0.112 (11)0.091 (9)0.020 (7)−0.007 (6)0.025 (8)
C60.057 (7)0.053 (6)0.101 (9)0.012 (5)0.012 (6)0.007 (6)
C70.038 (5)0.057 (6)0.073 (6)0.008 (4)−0.007 (5)0.020 (5)
C80.029 (5)0.040 (5)0.076 (6)0.004 (4)0.000 (4)0.014 (5)
C90.073 (8)0.043 (6)0.075 (7)0.025 (5)0.012 (6)−0.001 (5)
C100.077 (11)0.028 (8)0.051 (11)0.013 (7)−0.009 (9)0.005 (6)
C10'0.077 (11)0.028 (8)0.051 (11)0.013 (7)−0.009 (9)0.005 (6)
C110.090 (11)0.083 (9)0.152 (14)0.015 (8)0.003 (10)−0.003 (9)
C120.107 (13)0.053 (10)0.124 (18)0.022 (9)−0.024 (11)−0.044 (11)
C12'0.107 (13)0.053 (10)0.124 (18)0.022 (9)−0.024 (11)−0.044 (11)
C130.108 (10)0.037 (5)0.063 (6)−0.012 (6)0.010 (7)−0.020 (5)
C140.069 (7)0.041 (5)0.049 (5)−0.010 (5)−0.005 (5)−0.006 (4)
C150.087 (9)0.060 (7)0.054 (6)−0.032 (6)−0.018 (6)−0.005 (5)
C160.051 (6)0.051 (6)0.065 (6)−0.004 (5)−0.020 (5)−0.002 (5)
C170.049 (6)0.061 (6)0.065 (6)0.010 (5)0.004 (5)0.004 (5)
C180.045 (6)0.042 (5)0.049 (5)−0.008 (4)−0.003 (4)−0.001 (4)
C190.041 (5)0.049 (5)0.048 (5)−0.009 (4)0.002 (4)−0.005 (4)
C200.037 (6)0.062 (6)0.087 (7)0.013 (5)−0.010 (5)−0.024 (6)
C210.059 (7)0.064 (7)0.106 (9)0.000 (6)−0.017 (7)0.010 (7)
C220.159 (16)0.104 (11)0.080 (10)−0.022 (10)0.010 (10)0.006 (9)
Geometric parameters (Å, °) top
Lu1—O12.616 (7)C4—C51.402 (16)
Lu1—O22.368 (6)C4—H40.93
Lu1—O32.397 (6)C5—C61.342 (17)
Lu1—O42.634 (6)C5—H50.93
Lu1—O62.482 (8)C6—C71.429 (15)
Lu1—O72.493 (9)C6—H60.93
Lu1—O92.485 (7)C7—C81.385 (13)
Lu1—O102.447 (7)C7—C91.433 (14)
Lu1—O122.574 (7)C9—H90.93
Lu1—O132.514 (6)C10—C111.490 (10)
Cu1—O21.874 (6)C10—C121.500 (10)
Cu1—O31.909 (6)C10—H100.98
Cu1—O52.335 (8)C10'—C111.487 (9)
Cu1—N11.922 (8)C10'—C12'1.502 (10)
Cu1—N21.900 (8)C10'—H10'0.98
O1—C31.400 (11)C11—H11A0.96
O1—C21.458 (11)C11—H11B0.96
O2—C81.342 (11)C11—H11C0.96
O3—C191.301 (10)C11—H11D0.96
O4—C181.387 (10)C11—H11E0.96
O4—C201.481 (10)C11—H11F0.96
O5—C221.299 (14)C12—H12A0.97
O5—H5O0.82C12—H12B0.97
O6—N31.225 (12)C12'—H12C0.97
O7—N31.227 (13)C12'—H12D0.97
O8—N31.193 (11)C13—C141.488 (14)
O9—N41.278 (11)C13—H130.93
O10—N41.296 (11)C14—C151.355 (15)
O11—N41.196 (12)C14—C191.429 (12)
O12—N51.224 (10)C15—C161.383 (15)
O13—N51.242 (10)C15—H150.93
O14—N51.235 (10)C16—C171.367 (14)
N1—C91.305 (13)C16—H160.93
N1—C10'1.458 (9)C17—C181.405 (13)
N1—C101.466 (9)C17—H170.93
N2—C131.250 (13)C18—C191.387 (12)
N2—C12'1.459 (10)C20—C211.524 (14)
N2—C121.458 (10)C20—H20A0.97
C1—C21.567 (15)C20—H20B0.97
C1—H1A0.96C21—H21A0.96
C1—H1B0.96C21—H21B0.96
C1—H1C0.96C21—H21C0.96
C2—H2A0.97C22—H22A0.96
C2—H2B0.97C22—H22B0.96
C3—C81.376 (13)C22—H22C0.96
C3—C41.392 (14)
O2—Lu1—O363.0 (2)O1—C2—H2A109.7
O2—Lu1—O10127.6 (2)C1—C2—H2A109.7
O3—Lu1—O10120.6 (3)O1—C2—H2B109.7
O2—Lu1—O981.9 (2)C1—C2—H2B109.7
O3—Lu1—O980.3 (2)H2A—C2—H2B108.2
O10—Lu1—O951.7 (3)C8—C3—C4122.3 (9)
O2—Lu1—O676.1 (3)C8—C3—O1114.3 (8)
O3—Lu1—O6102.3 (3)C4—C3—O1123.4 (9)
O10—Lu1—O6136.6 (3)C3—C4—C5117.2 (11)
O9—Lu1—O6153.3 (3)C3—C4—H4121.4
O2—Lu1—O793.2 (3)C5—C4—H4121.4
O3—Lu1—O770.5 (3)C6—C5—C4120.7 (11)
O10—Lu1—O7139.0 (3)C6—C5—H5119.7
O9—Lu1—O7149.2 (3)C4—C5—H5119.7
O6—Lu1—O748.4 (3)C5—C6—C7122.4 (10)
O2—Lu1—O13157.8 (2)C5—C6—H6118.8
O3—Lu1—O13123.9 (2)C7—C6—H6118.8
O10—Lu1—O1369.8 (3)C8—C7—C9127.9 (9)
O9—Lu1—O13119.3 (3)C8—C7—C6116.6 (10)
O6—Lu1—O1381.7 (3)C9—C7—C6115.4 (9)
O7—Lu1—O1372.2 (3)O2—C8—C3116.5 (8)
O2—Lu1—O12119.5 (2)O2—C8—C7122.9 (9)
O3—Lu1—O12167.1 (2)C3—C8—C7120.6 (9)
O10—Lu1—O1269.0 (3)N1—C9—C7121.9 (8)
O9—Lu1—O12112.3 (3)N1—C9—H9119.0
O6—Lu1—O1267.6 (3)C7—C9—H9119.0
O7—Lu1—O1296.7 (3)N1—C10—C11120.1 (12)
O13—Lu1—O1248.7 (2)N1—C10—C12105.3 (17)
O2—Lu1—O161.3 (2)C11—C10—C12104.3 (11)
O3—Lu1—O1121.59 (19)N1—C10—H10108.9
O10—Lu1—O182.4 (2)C11—C10—H10108.9
O9—Lu1—O175.8 (2)C12—C10—H10108.9
O6—Lu1—O180.5 (3)N1—C10'—C11120.9 (11)
O7—Lu1—O1128.1 (3)N1—C10'—C12'107.1 (18)
O13—Lu1—O1114.3 (2)C11—C10'—C12'105.2 (12)
O12—Lu1—O166.0 (2)N1—C10'—H10'107.6
O2—Lu1—O4122.4 (2)C11—C10'—H10'107.6
O3—Lu1—O460.70 (18)C12'—C10'—H10'107.6
O10—Lu1—O475.1 (2)C10—C11—H11A109.5
O9—Lu1—O477.8 (2)C10—C11—H11B109.5
O6—Lu1—O4126.9 (3)H11A—C11—H11B109.5
O7—Lu1—O479.4 (3)C10—C11—H11C109.5
O13—Lu1—O472.4 (2)H11A—C11—H11C109.5
O12—Lu1—O4118.2 (2)H11B—C11—H11C109.5
O1—Lu1—O4152.5 (2)C10'—C11—H11D109.3
O2—Cu1—O382.3 (3)C10'—C11—H11E110.2
O2—Cu1—N2172.7 (3)H11D—C11—H11E109.5
O3—Cu1—N295.1 (3)C10'—C11—H11F108.9
O2—Cu1—N196.5 (3)H11D—C11—H11F109.5
O3—Cu1—N1171.4 (3)H11E—C11—H11F109.5
N2—Cu1—N185.0 (3)N2—C12—C10108.2 (14)
O2—Cu1—O596.4 (3)N2—C12—H12A110.1
O3—Cu1—O595.7 (3)C10—C12—H12A110.1
N2—Cu1—O590.6 (3)N2—C12—H12B110.1
N1—Cu1—O592.9 (4)C10—C12—H12B110.1
C3—O1—C2119.6 (8)H12A—C12—H12B108.4
C3—O1—Lu1116.5 (5)N2—C12'—C10'107.1 (15)
C2—O1—Lu1123.7 (6)N2—C12'—H12C110.3
C8—O2—Cu1124.5 (5)C10'—C12'—H12C110.3
C8—O2—Lu1127.1 (5)N2—C12'—H12D110.3
Cu1—O2—Lu1108.0 (3)C10'—C12'—H12D110.3
C19—O3—Cu1125.1 (6)H12C—C12'—H12D108.5
C19—O3—Lu1129.2 (5)N2—C13—C14125.8 (9)
Cu1—O3—Lu1105.7 (3)N2—C13—H13117.1
C18—O4—C20117.2 (7)C14—C13—H13117.1
C18—O4—Lu1118.2 (5)C15—C14—C19120.5 (9)
C20—O4—Lu1124.6 (5)C15—C14—C13118.6 (9)
C22—O5—Cu1128.7 (9)C19—C14—C13120.9 (9)
C22—O5—H5O115.7C16—C15—C14121.0 (9)
Cu1—O5—H5O115.7C16—C15—H15119.5
N3—O6—Lu199.5 (7)C14—C15—H15119.5
N3—O7—Lu198.9 (7)C17—C16—C15119.9 (9)
N4—O9—Lu196.7 (6)C17—C16—H16120.0
N4—O10—Lu197.9 (6)C15—C16—H16120.0
N5—O12—Lu195.8 (5)C16—C17—C18120.2 (9)
N5—O13—Lu198.4 (5)C16—C17—H17119.9
C9—N1—C10'120.7 (11)C18—C17—H17119.9
C9—N1—C10122.2 (10)C19—C18—O4114.3 (8)
C9—N1—Cu1125.2 (6)C19—C18—C17120.4 (8)
C10'—N1—Cu1111.0 (8)O4—C18—C17125.2 (8)
C10—N1—Cu1111.0 (8)O3—C19—C18117.0 (8)
C13—N2—C12'119.9 (13)O3—C19—C14125.3 (8)
C13—N2—C12122.0 (13)C18—C19—C14117.7 (8)
C13—N2—Cu1125.9 (6)O4—C20—C21112.5 (9)
C12'—N2—Cu1112.7 (12)O4—C20—H20A109.1
C12—N2—Cu1111.9 (12)C21—C20—H20A109.1
O8—N3—O7123.8 (11)O4—C20—H20B109.1
O8—N3—O6123.5 (11)C21—C20—H20B109.1
O7—N3—O6112.7 (9)H20A—C20—H20B107.8
O11—N4—O9126.5 (10)C20—C21—H21A109.5
O11—N4—O10120.1 (10)C20—C21—H21B109.5
O9—N4—O10113.4 (9)H21A—C21—H21B109.5
O13—N5—O12116.7 (8)C20—C21—H21C109.5
O13—N5—O14122.1 (9)H21A—C21—H21C109.5
O12—N5—O14121.1 (9)H21B—C21—H21C109.5
C2—C1—H1A109.5O5—C22—H22A109.5
C2—C1—H1B109.5O5—C22—H22B109.5
H1A—C1—H1B109.5H22A—C22—H22B109.5
C2—C1—H1C109.5O5—C22—H22C109.5
H1A—C1—H1C109.5H22A—C22—H22C109.5
H1B—C1—H1C109.5H22B—C22—H22C109.5
O1—C2—C1109.7 (9)
O2—Lu1—O1—C3−17.2 (6)O6—Lu1—O12—N5−102.2 (6)
O3—Lu1—O1—C3−36.6 (7)O7—Lu1—O12—N5−62.6 (6)
O10—Lu1—O1—C3−158.0 (6)O13—Lu1—O12—N5−3.4 (5)
O9—Lu1—O1—C3−105.6 (6)O1—Lu1—O12—N5168.5 (7)
O6—Lu1—O1—C362.1 (6)O4—Lu1—O12—N518.9 (7)
O7—Lu1—O1—C352.4 (7)O2—Lu1—O13—N568.7 (9)
O13—Lu1—O1—C3138.3 (6)O3—Lu1—O13—N5170.1 (5)
O12—Lu1—O1—C3131.7 (6)O10—Lu1—O13—N5−76.0 (6)
O4—Lu1—O1—C3−122.9 (6)O9—Lu1—O13—N5−91.6 (6)
O2—Lu1—O1—C2158.6 (7)O6—Lu1—O13—N570.8 (6)
O3—Lu1—O1—C2139.3 (6)O7—Lu1—O13—N5119.7 (6)
O10—Lu1—O1—C217.9 (7)O12—Lu1—O13—N53.4 (5)
O9—Lu1—O1—C270.3 (7)O1—Lu1—O13—N5−4.7 (6)
O6—Lu1—O1—C2−122.1 (7)O4—Lu1—O13—N5−156.1 (6)
O7—Lu1—O1—C2−131.7 (7)O2—Cu1—N1—C9−3.2 (9)
O13—Lu1—O1—C2−45.8 (7)N2—Cu1—N1—C9−176.1 (9)
O12—Lu1—O1—C2−52.5 (7)O5—Cu1—N1—C993.6 (9)
O4—Lu1—O1—C252.9 (8)O2—Cu1—N1—C10'156.9 (11)
O3—Cu1—O2—C8−178.4 (7)N2—Cu1—N1—C10'−15.9 (11)
N1—Cu1—O2—C810.2 (7)O5—Cu1—N1—C10'−106.3 (11)
O5—Cu1—O2—C8−83.5 (7)O2—Cu1—N1—C10−169.1 (10)
O3—Cu1—O2—Lu18.3 (3)N2—Cu1—N1—C1018.0 (10)
N1—Cu1—O2—Lu1−163.1 (3)O5—Cu1—N1—C10−72.3 (10)
O5—Cu1—O2—Lu1103.2 (3)O3—Cu1—N2—C1312.6 (9)
O3—Lu1—O2—C8179.5 (8)N1—Cu1—N2—C13−176.0 (9)
O10—Lu1—O2—C870.3 (8)O5—Cu1—N2—C13−83.1 (9)
O9—Lu1—O2—C896.3 (7)O3—Cu1—N2—C12'178.6 (18)
O6—Lu1—O2—C8−68.6 (7)N1—Cu1—N2—C12'−10.0 (18)
O7—Lu1—O2—C8−114.3 (7)O5—Cu1—N2—C12'82.9 (18)
O13—Lu1—O2—C8−66.5 (10)O3—Cu1—N2—C12−162.6 (17)
O12—Lu1—O2—C8−14.8 (8)N1—Cu1—N2—C128.8 (17)
O1—Lu1—O2—C818.0 (7)O5—Cu1—N2—C12101.7 (17)
O4—Lu1—O2—C8166.2 (7)Lu1—O7—N3—O8−175.4 (8)
O3—Lu1—O2—Cu1−7.3 (3)Lu1—O7—N3—O66.0 (10)
O10—Lu1—O2—Cu1−116.5 (3)Lu1—O6—N3—O8175.4 (8)
O9—Lu1—O2—Cu1−90.6 (3)Lu1—O6—N3—O7−6.0 (10)
O6—Lu1—O2—Cu1104.5 (4)Lu1—O9—N4—O11−175.5 (11)
O7—Lu1—O2—Cu158.8 (4)Lu1—O9—N4—O104.7 (9)
O13—Lu1—O2—Cu1106.6 (6)Lu1—O10—N4—O11175.4 (10)
O12—Lu1—O2—Cu1158.3 (3)Lu1—O10—N4—O9−4.8 (9)
O1—Lu1—O2—Cu1−168.9 (4)Lu1—O13—N5—O12−6.0 (9)
O4—Lu1—O2—Cu1−20.7 (4)Lu1—O13—N5—O14176.9 (7)
O2—Cu1—O3—C19173.7 (8)Lu1—O12—N5—O135.8 (9)
N2—Cu1—O3—C19−13.2 (8)Lu1—O12—N5—O14−177.0 (7)
O5—Cu1—O3—C1977.9 (7)C3—O1—C2—C168.5 (12)
O2—Cu1—O3—Lu1−8.1 (3)Lu1—O1—C2—C1−107.2 (9)
N2—Cu1—O3—Lu1165.1 (3)C2—O1—C3—C8−159.1 (8)
O5—Cu1—O3—Lu1−103.9 (3)Lu1—O1—C3—C816.9 (10)
O2—Lu1—O3—C19−174.7 (8)C2—O1—C3—C420.3 (14)
O10—Lu1—O3—C19−55.2 (8)Lu1—O1—C3—C4−163.7 (8)
O9—Lu1—O3—C19−89.0 (8)C8—C3—C4—C5−3.0 (16)
O6—Lu1—O3—C19118.0 (7)O1—C3—C4—C5177.7 (10)
O7—Lu1—O3—C1980.9 (8)C3—C4—C5—C64.4 (18)
O13—Lu1—O3—C1929.9 (8)C4—C5—C6—C7−3.3 (19)
O12—Lu1—O3—C1980.8 (13)C5—C6—C7—C80.5 (17)
O1—Lu1—O3—C19−155.7 (7)C5—C6—C7—C9−178.3 (11)
O4—Lu1—O3—C19−7.7 (7)Cu1—O2—C8—C3171.5 (6)
O2—Lu1—O3—Cu17.1 (3)Lu1—O2—C8—C3−16.4 (11)
O10—Lu1—O3—Cu1126.7 (3)Cu1—O2—C8—C7−10.8 (12)
O9—Lu1—O3—Cu192.8 (3)Lu1—O2—C8—C7161.2 (7)
O6—Lu1—O3—Cu1−60.1 (3)C4—C3—C8—O2178.0 (9)
O7—Lu1—O3—Cu1−97.2 (4)O1—C3—C8—O2−2.6 (12)
O13—Lu1—O3—Cu1−148.3 (3)C4—C3—C8—C70.4 (15)
O12—Lu1—O3—Cu1−97.3 (10)O1—C3—C8—C7179.7 (8)
O1—Lu1—O3—Cu126.1 (4)C9—C7—C8—O22.1 (16)
O4—Lu1—O3—Cu1174.2 (4)C6—C7—C8—O2−176.6 (9)
O2—Lu1—O4—C1818.9 (7)C9—C7—C8—C3179.6 (10)
O3—Lu1—O4—C185.3 (6)C6—C7—C8—C31.0 (14)
O10—Lu1—O4—C18144.2 (6)C10'—N1—C9—C7−161.7 (12)
O9—Lu1—O4—C1890.9 (6)C10—N1—C9—C7161.1 (12)
O6—Lu1—O4—C18−78.0 (7)Cu1—N1—C9—C7−3.3 (15)
O7—Lu1—O4—C18−68.2 (6)C8—C7—C9—N15.5 (17)
O13—Lu1—O4—C18−142.7 (6)C6—C7—C9—N1−175.8 (10)
O12—Lu1—O4—C18−160.1 (6)C9—N1—C10—C1137 (2)
O1—Lu1—O4—C18108.1 (6)C10'—N1—C10—C11−60.1 (15)
O2—Lu1—O4—C20−161.9 (7)Cu1—N1—C10—C11−156.2 (13)
O3—Lu1—O4—C20−175.6 (7)C9—N1—C10—C12154.4 (17)
O10—Lu1—O4—C20−36.6 (7)C10'—N1—C10—C1257 (3)
O9—Lu1—O4—C20−89.9 (7)Cu1—N1—C10—C12−39.2 (18)
O6—Lu1—O4—C20101.1 (7)C9—N1—C10'—C11−41 (2)
O7—Lu1—O4—C20111.0 (7)C10—N1—C10'—C1161.2 (14)
O13—Lu1—O4—C2036.5 (7)Cu1—N1—C10'—C11157.5 (16)
O12—Lu1—O4—C2019.1 (8)C9—N1—C10'—C12'−161.7 (16)
O1—Lu1—O4—C20−72.7 (8)C10—N1—C10'—C12'−59 (3)
O2—Cu1—O5—C229.4 (14)Cu1—N1—C10'—C12'37.2 (18)
O3—Cu1—O5—C2292.3 (13)N1—C10'—C11—C10−61.2 (14)
N2—Cu1—O5—C22−172.5 (13)C12'—C10'—C11—C1060 (3)
N1—Cu1—O5—C22−87.5 (13)N1—C10—C11—C10'59.8 (14)
O2—Lu1—O6—N3−103.6 (7)C12—C10—C11—C10'−58 (3)
O3—Lu1—O6—N3−45.8 (7)C13—N2—C12—C10151.7 (17)
O10—Lu1—O6—N3125.7 (7)C12'—N2—C12—C1063 (6)
O9—Lu1—O6—N3−138.7 (6)Cu1—N2—C12—C10−33 (3)
O7—Lu1—O6—N33.7 (6)N1—C10—C12—N246 (3)
O13—Lu1—O6—N377.2 (7)C11—C10—C12—N2173 (2)
O12—Lu1—O6—N3125.9 (7)C13—N2—C12'—C10'−160.6 (17)
O1—Lu1—O6—N3−166.2 (7)C12—N2—C12'—C10'−59 (5)
O4—Lu1—O6—N316.7 (8)Cu1—N2—C12'—C10'32 (3)
O2—Lu1—O7—N364.6 (6)N1—C10'—C12'—N2−44 (3)
O3—Lu1—O7—N3124.4 (7)C11—C10'—C12'—N2−174 (2)
O10—Lu1—O7—N3−121.1 (7)C12'—N2—C13—C14−170 (2)
O9—Lu1—O7—N3144.0 (6)C12—N2—C13—C14170 (2)
O6—Lu1—O7—N3−3.6 (6)Cu1—N2—C13—C14−5.1 (16)
O13—Lu1—O7—N3−98.3 (7)N2—C13—C14—C15175.5 (10)
O12—Lu1—O7—N3−55.6 (7)N2—C13—C14—C19−6.5 (16)
O1—Lu1—O7—N39.1 (8)C19—C14—C15—C162.1 (16)
O4—Lu1—O7—N3−173.1 (7)C13—C14—C15—C16−179.9 (9)
O2—Lu1—O9—N4−156.7 (6)C14—C15—C16—C17−4.3 (16)
O3—Lu1—O9—N4139.4 (6)C15—C16—C17—C181.1 (15)
O10—Lu1—O9—N4−2.9 (6)C20—O4—C18—C19177.2 (8)
O6—Lu1—O9—N4−122.4 (8)Lu1—O4—C18—C19−3.6 (10)
O7—Lu1—O9—N4120.7 (8)C20—O4—C18—C171.7 (13)
O13—Lu1—O9—N415.9 (7)Lu1—O4—C18—C17−179.1 (7)
O12—Lu1—O9—N4−38.1 (6)C16—C17—C18—C194.3 (15)
O1—Lu1—O9—N4−94.3 (6)C16—C17—C18—O4179.6 (9)
O4—Lu1—O9—N477.5 (6)Cu1—O3—C19—C18−173.2 (6)
O2—Lu1—O10—N436.4 (7)Lu1—O3—C19—C189.0 (12)
O3—Lu1—O10—N4−41.5 (7)Cu1—O3—C19—C146.3 (13)
O9—Lu1—O10—N42.9 (6)Lu1—O3—C19—C14−171.5 (6)
O6—Lu1—O10—N4148.2 (6)O4—C18—C19—O3−2.5 (12)
O7—Lu1—O10—N4−136.5 (6)C17—C18—C19—O3173.2 (8)
O13—Lu1—O10—N4−159.7 (7)O4—C18—C19—C14178.0 (8)
O12—Lu1—O10—N4148.0 (7)C17—C18—C19—C14−6.3 (13)
O1—Lu1—O10—N480.8 (6)C15—C14—C19—O3−176.4 (9)
O4—Lu1—O10—N4−83.2 (6)C13—C14—C19—O35.7 (15)
O2—Lu1—O12—N5−160.1 (5)C15—C14—C19—C183.2 (14)
O3—Lu1—O12—N5−62.5 (13)C13—C14—C19—C18−174.8 (9)
O10—Lu1—O12—N577.7 (6)C18—O4—C20—C2177.7 (10)
O9—Lu1—O12—N5106.7 (6)Lu1—O4—C20—C21−101.5 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O14i0.822.132.93 (1)164
Symmetry codes: (i) −x+1, y+1/2, −z+1/2.
Table 1
Selected geometric parameters (Å) top
Lu1—O12.616 (7)Lu1—O122.574 (7)
Lu1—O22.368 (6)Lu1—O132.514 (6)
Lu1—O32.397 (6)Cu1—O21.874 (6)
Lu1—O42.634 (6)Cu1—O31.909 (6)
Lu1—O62.482 (8)Cu1—O52.335 (8)
Lu1—O72.493 (9)Cu1—N11.922 (8)
Lu1—O92.485 (7)Cu1—N21.900 (8)
Lu1—O102.447 (7)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O14i0.822.132.93 (1)164
Symmetry codes: (i) −x+1, y+1/2, −z+1/2.
Acknowledgements top

The authors thank the Department of Education of Jiangxi Province (grant Nos. 2007317 and 05YB195) and the University of Malaya for supporting this study.

references
References top

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