[μ₂-N,N′-Bis(2-oxy-3-ethoxy­benzyl­idene)­propane-1,2-diamine]­(methanol)­trinitratocopper(II)lutetium(III)

The Cu atom in the title compound (systematic name: {6,6′-dieth­oxy-2,2′-[propane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato-1κ⁴O¹,O^1′,­O⁶,O^6′:2κ⁴O¹,N,N′,O^1′}(methanol-2κO)trinitrato-1κ⁶O,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 Cu^II atom exists in a square-pyramidal geometry and the Lu^III 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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.015 Å
• Disorder in main residue
• R factor = 0.059
• wR factor = 0.196
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level A
ABSTM02_ALERT_3_A  The ratio of expected to reported Tmax/Tmin(RR') is < 0.50
            Tmin and Tmax reported:      0.183     0.733
            Tmin(prime) and Tmax expected:      0.432     0.718
            RR(prime) =      0.415
            Please check that your absorption correction is appropriate.

Author Response: The diffraction data are of marginal quality, and there is a problem of absorption. The raw intensities were processed by using the multi-scan absorption program, and a model with heavy atoms was used. The transmission factors are those given by the program.

PLAT061_ALERT_3_A Tmax/Tmin Range Test RR' too Large .............       0.41

Author Response: As above.

PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        C11

Author Response: The atom is part of a disordered group.

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O6

Author Response: The atom is part of a disordered group.

PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O7

Author Response: The atom is part of a disordered group.

PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C12

Author Response: The atom is part of a disordered group.

PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C12'

Author Response: The atom is part of a disordered group.

PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C10'

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5

Author Response: The atom is part of a disordered group.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O12

Author Response: The atom is part of a disordered group.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13

Author Response: The atom is part of a disordered group.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         15

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C22 H28 Cu1 Lu1 N5 O14
            Atom count from _chemical_formula_moiety:
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         10

   3 ALERT level A = In general: serious problem
   7 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

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)χoppergadolinium (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

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.

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.2–1.5U_eq(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

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

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)

Crystal data

[CuLu(C21H22N2O4)(CH4O)(NO3)3]	F(000) = 1628
Mr = 825.00	Dx = 1.865 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4544 reflections
a = 9.1795 (5) Å	θ = 2.4–22.2°
b = 20.407 (1) Å	µ = 4.14 mm^−1
c = 15.7058 (9) Å	T = 295 K
β = 93.126 (1)°	Block, red
V = 2937.7 (3) Å^3	0.20 × 0.09 × 0.08 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer	6636 independent reflections
Radiation source: fine-focus sealed tube	3788 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.183, Tmax = 0.733	k = −26→26
21167 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1059P)^2] where P = (Fo^2 + 2Fc^2)/3
6636 reflections	(Δ/σ)max = 0.001
394 parameters	Δρmax = 1.20 e Å^−3
10 restraints	Δρmin = −1.29 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Lu1	0.36449 (5)	0.34232 (2)	0.25150 (3)	0.05488 (19)
Cu1	0.32833 (12)	0.50585 (5)	0.30039 (7)	0.0460 (3)
O1	0.1485 (8)	0.3477 (3)	0.1360 (4)	0.0525 (16)
O2	0.2284 (7)	0.4406 (3)	0.2367 (4)	0.0550 (16)
O3	0.4753 (7)	0.4397 (3)	0.3108 (4)	0.0519 (16)
O4	0.6441 (7)	0.3413 (3)	0.2989 (4)	0.0489 (15)
O5	0.4254 (11)	0.5592 (4)	0.1848 (5)	0.101 (3)
H5O	0.4865	0.5875	0.1969	0.122*
O6	0.1569 (10)	0.3251 (5)	0.3439 (6)	0.097 (3)
O7	0.3518 (12)	0.3407 (5)	0.4097 (5)	0.099 (3)
O8	0.1587 (12)	0.3342 (4)	0.4790 (6)	0.093 (3)
O9	0.4776 (8)	0.3859 (4)	0.1229 (5)	0.067 (2)
O10	0.4809 (9)	0.2812 (4)	0.1396 (5)	0.071 (2)
O11	0.5937 (12)	0.3224 (5)	0.0349 (6)	0.104 (3)
O12	0.2362 (8)	0.2317 (3)	0.2230 (6)	0.075 (2)
O13	0.4277 (8)	0.2285 (3)	0.3023 (5)	0.067 (2)
O14	0.3179 (10)	0.1381 (3)	0.2648 (6)	0.086 (3)
N1	0.1675 (10)	0.5659 (3)	0.3038 (6)	0.064 (2)
N2	0.4260 (9)	0.5652 (3)	0.3773 (5)	0.053 (2)
N3	0.2196 (11)	0.3338 (4)	0.4138 (6)	0.056 (2)
N4	0.5218 (12)	0.3308 (5)	0.0953 (7)	0.070 (3)
N5	0.3281 (10)	0.1984 (4)	0.2624 (5)	0.055 (2)
C1	0.1685 (19)	0.3436 (7)	−0.0203 (8)	0.107 (5)
H1A	0.1514	0.3160	−0.0693	0.160*
H1B	0.2687	0.3574	−0.0167	0.160*
H1C	0.1062	0.3813	−0.0253	0.160*
C2	0.1348 (14)	0.3045 (5)	0.0622 (6)	0.069 (3)
H2A	0.0367	0.2868	0.0565	0.082*
H2B	0.2025	0.2681	0.0698	0.082*
C3	0.0473 (10)	0.3983 (4)	0.1446 (6)	0.050 (2)
C4	−0.0902 (14)	0.3990 (6)	0.1026 (7)	0.081 (4)
H4	−0.1196	0.3659	0.0647	0.097*
C5	−0.1824 (13)	0.4515 (7)	0.1197 (8)	0.086 (4)
H5	−0.2774	0.4521	0.0959	0.103*
C6	−0.1351 (12)	0.5010 (5)	0.1702 (8)	0.070 (3)
H6	−0.1970	0.5363	0.1781	0.084*
C7	0.0070 (10)	0.5015 (5)	0.2122 (7)	0.056 (2)
C8	0.0955 (9)	0.4482 (4)	0.1980 (6)	0.048 (2)
C9	0.0390 (13)	0.5572 (5)	0.2657 (7)	0.063 (3)
H9	−0.0338	0.5879	0.2735	0.076*
C10	0.2161 (17)	0.6300 (6)	0.3366 (12)	0.053 (4)	0.50
H10	0.2633	0.6537	0.2913	0.063*	0.50
C10'	0.187 (2)	0.6104 (6)	0.3762 (10)	0.053 (4)	0.50
H10'	0.1607	0.5865	0.4273	0.063*	0.50
C11	0.1109 (15)	0.6748 (6)	0.3762 (10)	0.108 (5)
H11A	0.1626	0.7116	0.4011	0.163*	0.50
H11B	0.0622	0.6517	0.4197	0.163*	0.50
H11C	0.0402	0.6899	0.3334	0.163*	0.50
H11D	0.0074	0.6677	0.3727	0.163*	0.50
H11E	0.1379	0.6985	0.4275	0.163*	0.50
H11F	0.1381	0.6996	0.3277	0.163*	0.50
C12	0.328 (3)	0.6153 (14)	0.4072 (18)	0.096 (8)	0.50
H12A	0.3824	0.6547	0.4226	0.115*	0.50
H12B	0.2805	0.5998	0.4570	0.115*	0.50
C12'	0.347 (2)	0.6264 (10)	0.386 (3)	0.096 (8)	0.50
H12C	0.3728	0.6575	0.3429	0.115*	0.50
H12D	0.3696	0.6456	0.4419	0.115*	0.50
C13	0.5558 (15)	0.5608 (5)	0.4052 (7)	0.069 (3)
H13	0.5925	0.5951	0.4390	0.083*
C14	0.6568 (12)	0.5056 (4)	0.3894 (6)	0.053 (2)
C15	0.7976 (13)	0.5104 (5)	0.4195 (6)	0.068 (3)
H15	0.8283	0.5477	0.4494	0.081*
C16	0.8962 (11)	0.4607 (5)	0.4065 (6)	0.057 (2)
H16	0.9939	0.4659	0.4242	0.068*
C17	0.8500 (11)	0.4039 (5)	0.3676 (6)	0.058 (3)
H17	0.9161	0.3701	0.3597	0.070*
C18	0.7030 (10)	0.3963 (4)	0.3395 (6)	0.046 (2)
C19	0.6058 (10)	0.4479 (4)	0.3458 (5)	0.046 (2)
C20	0.7437 (10)	0.2855 (5)	0.2863 (7)	0.062 (3)
H20A	0.8354	0.3019	0.2670	0.075*
H20B	0.7011	0.2570	0.2422	0.075*
C21	0.7735 (12)	0.2457 (6)	0.3676 (8)	0.077 (3)
H21A	0.7709	0.1998	0.3541	0.115*
H21B	0.7004	0.2553	0.4072	0.115*
H21C	0.8680	0.2569	0.3926	0.115*
C22	0.3956 (19)	0.5501 (8)	0.1039 (9)	0.114 (5)
H22A	0.4755	0.5654	0.0723	0.171*
H22B	0.3088	0.5739	0.0865	0.171*
H22C	0.3805	0.5042	0.0931	0.171*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Lu1	0.0553 (3)	0.0411 (3)	0.0676 (3)	0.00042 (19)	−0.0023 (2)	−0.0050 (2)
Cu1	0.0493 (7)	0.0293 (5)	0.0591 (7)	0.0017 (5)	0.0012 (5)	−0.0057 (5)
O1	0.057 (4)	0.041 (4)	0.058 (4)	0.000 (3)	−0.010 (3)	−0.003 (3)
O2	0.054 (4)	0.036 (3)	0.074 (4)	0.012 (3)	−0.006 (3)	−0.009 (3)
O3	0.047 (4)	0.036 (3)	0.070 (4)	0.008 (3)	−0.018 (3)	−0.012 (3)
O4	0.047 (4)	0.034 (3)	0.065 (4)	−0.006 (3)	0.001 (3)	−0.011 (3)
O5	0.135 (9)	0.086 (6)	0.084 (6)	−0.053 (6)	0.017 (6)	0.002 (5)
O6	0.074 (6)	0.145 (9)	0.072 (6)	0.021 (6)	0.019 (5)	0.023 (5)
O7	0.101 (8)	0.132 (9)	0.062 (5)	−0.032 (6)	−0.010 (5)	−0.003 (5)
O8	0.138 (9)	0.076 (6)	0.070 (6)	−0.008 (5)	0.040 (6)	0.007 (4)
O9	0.066 (5)	0.063 (5)	0.074 (5)	−0.008 (4)	0.009 (4)	0.015 (4)
O10	0.083 (6)	0.060 (5)	0.071 (5)	0.005 (4)	0.012 (4)	−0.019 (4)
O11	0.119 (8)	0.114 (7)	0.085 (6)	−0.026 (6)	0.061 (6)	−0.014 (5)
O12	0.058 (5)	0.046 (4)	0.119 (6)	−0.013 (4)	−0.023 (4)	0.011 (4)
O13	0.057 (5)	0.045 (4)	0.096 (5)	−0.009 (3)	−0.018 (4)	0.011 (4)
O14	0.101 (6)	0.031 (4)	0.127 (7)	−0.013 (4)	0.006 (5)	−0.014 (4)
N1	0.064 (6)	0.035 (4)	0.092 (6)	0.016 (4)	−0.007 (5)	−0.004 (4)
N2	0.061 (6)	0.031 (4)	0.067 (5)	0.003 (4)	−0.006 (4)	−0.008 (4)
N3	0.069 (7)	0.041 (5)	0.060 (6)	−0.002 (4)	0.015 (5)	−0.010 (4)
N4	0.072 (7)	0.066 (7)	0.071 (6)	−0.020 (5)	−0.005 (5)	−0.001 (5)
N5	0.070 (6)	0.029 (4)	0.068 (5)	0.000 (4)	0.023 (5)	−0.003 (4)
C1	0.124 (14)	0.143 (14)	0.054 (7)	0.011 (10)	0.007 (8)	0.003 (8)
C2	0.086 (8)	0.054 (6)	0.064 (7)	−0.005 (6)	−0.016 (6)	−0.006 (5)
C3	0.046 (6)	0.044 (5)	0.058 (6)	0.002 (4)	−0.005 (4)	0.009 (4)
C4	0.101 (10)	0.066 (8)	0.071 (8)	0.012 (7)	−0.027 (7)	0.000 (6)
C5	0.054 (7)	0.112 (11)	0.091 (9)	0.020 (7)	−0.007 (6)	0.025 (8)
C6	0.057 (7)	0.053 (6)	0.101 (9)	0.012 (5)	0.012 (6)	0.007 (6)
C7	0.038 (5)	0.057 (6)	0.073 (6)	0.008 (4)	−0.007 (5)	0.020 (5)
C8	0.029 (5)	0.040 (5)	0.076 (6)	0.004 (4)	0.000 (4)	0.014 (5)
C9	0.073 (8)	0.043 (6)	0.075 (7)	0.025 (5)	0.012 (6)	−0.001 (5)
C10	0.077 (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)
C11	0.090 (11)	0.083 (9)	0.152 (14)	0.015 (8)	0.003 (10)	−0.003 (9)
C12	0.107 (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)
C13	0.108 (10)	0.037 (5)	0.063 (6)	−0.012 (6)	0.010 (7)	−0.020 (5)
C14	0.069 (7)	0.041 (5)	0.049 (5)	−0.010 (5)	−0.005 (5)	−0.006 (4)
C15	0.087 (9)	0.060 (7)	0.054 (6)	−0.032 (6)	−0.018 (6)	−0.005 (5)
C16	0.051 (6)	0.051 (6)	0.065 (6)	−0.004 (5)	−0.020 (5)	−0.002 (5)
C17	0.049 (6)	0.061 (6)	0.065 (6)	0.010 (5)	0.004 (5)	0.004 (5)
C18	0.045 (6)	0.042 (5)	0.049 (5)	−0.008 (4)	−0.003 (4)	−0.001 (4)
C19	0.041 (5)	0.049 (5)	0.048 (5)	−0.009 (4)	0.002 (4)	−0.005 (4)
C20	0.037 (6)	0.062 (6)	0.087 (7)	0.013 (5)	−0.010 (5)	−0.024 (6)
C21	0.059 (7)	0.064 (7)	0.106 (9)	0.000 (6)	−0.017 (7)	0.010 (7)
C22	0.159 (16)	0.104 (11)	0.080 (10)	−0.022 (10)	0.010 (10)	0.006 (9)

Geometric parameters (Å, º)

Lu1—O1	2.616 (7)	C4—C5	1.402 (16)
Lu1—O2	2.368 (6)	C4—H4	0.93
Lu1—O3	2.397 (6)	C5—C6	1.342 (17)
Lu1—O4	2.634 (6)	C5—H5	0.93
Lu1—O6	2.482 (8)	C6—C7	1.429 (15)
Lu1—O7	2.493 (9)	C6—H6	0.93
Lu1—O9	2.485 (7)	C7—C8	1.385 (13)
Lu1—O10	2.447 (7)	C7—C9	1.433 (14)
Lu1—O12	2.574 (7)	C9—H9	0.93
Lu1—O13	2.514 (6)	C10—C11	1.490 (10)
Cu1—O2	1.874 (6)	C10—C12	1.500 (10)
Cu1—O3	1.909 (6)	C10—H10	0.98
Cu1—O5	2.335 (8)	C10'—C11	1.487 (9)
Cu1—N1	1.922 (8)	C10'—C12'	1.502 (10)
Cu1—N2	1.900 (8)	C10'—H10'	0.98
O1—C3	1.400 (11)	C11—H11A	0.96
O1—C2	1.458 (11)	C11—H11B	0.96
O2—C8	1.342 (11)	C11—H11C	0.96
O3—C19	1.301 (10)	C11—H11D	0.96
O4—C18	1.387 (10)	C11—H11E	0.96
O4—C20	1.481 (10)	C11—H11F	0.96
O5—C22	1.299 (14)	C12—H12A	0.97
O5—H5O	0.82	C12—H12B	0.97
O6—N3	1.225 (12)	C12'—H12C	0.97
O7—N3	1.227 (13)	C12'—H12D	0.97
O8—N3	1.193 (11)	C13—C14	1.488 (14)
O9—N4	1.278 (11)	C13—H13	0.93
O10—N4	1.296 (11)	C14—C15	1.355 (15)
O11—N4	1.196 (12)	C14—C19	1.429 (12)
O12—N5	1.224 (10)	C15—C16	1.383 (15)
O13—N5	1.242 (10)	C15—H15	0.93
O14—N5	1.235 (10)	C16—C17	1.367 (14)
N1—C9	1.305 (13)	C16—H16	0.93
N1—C10'	1.458 (9)	C17—C18	1.405 (13)
N1—C10	1.466 (9)	C17—H17	0.93
N2—C13	1.250 (13)	C18—C19	1.387 (12)
N2—C12'	1.459 (10)	C20—C21	1.524 (14)
N2—C12	1.458 (10)	C20—H20A	0.97
C1—C2	1.567 (15)	C20—H20B	0.97
C1—H1A	0.96	C21—H21A	0.96
C1—H1B	0.96	C21—H21B	0.96
C1—H1C	0.96	C21—H21C	0.96
C2—H2A	0.97	C22—H22A	0.96
C2—H2B	0.97	C22—H22B	0.96
C3—C8	1.376 (13)	C22—H22C	0.96
C3—C4	1.392 (14)
O2—Lu1—O3	63.0 (2)	O1—C2—H2A	109.7
O2—Lu1—O10	127.6 (2)	C1—C2—H2A	109.7
O3—Lu1—O10	120.6 (3)	O1—C2—H2B	109.7
O2—Lu1—O9	81.9 (2)	C1—C2—H2B	109.7
O3—Lu1—O9	80.3 (2)	H2A—C2—H2B	108.2
O10—Lu1—O9	51.7 (3)	C8—C3—C4	122.3 (9)
O2—Lu1—O6	76.1 (3)	C8—C3—O1	114.3 (8)
O3—Lu1—O6	102.3 (3)	C4—C3—O1	123.4 (9)
O10—Lu1—O6	136.6 (3)	C3—C4—C5	117.2 (11)
O9—Lu1—O6	153.3 (3)	C3—C4—H4	121.4
O2—Lu1—O7	93.2 (3)	C5—C4—H4	121.4
O3—Lu1—O7	70.5 (3)	C6—C5—C4	120.7 (11)
O10—Lu1—O7	139.0 (3)	C6—C5—H5	119.7
O9—Lu1—O7	149.2 (3)	C4—C5—H5	119.7
O6—Lu1—O7	48.4 (3)	C5—C6—C7	122.4 (10)
O2—Lu1—O13	157.8 (2)	C5—C6—H6	118.8
O3—Lu1—O13	123.9 (2)	C7—C6—H6	118.8
O10—Lu1—O13	69.8 (3)	C8—C7—C9	127.9 (9)
O9—Lu1—O13	119.3 (3)	C8—C7—C6	116.6 (10)
O6—Lu1—O13	81.7 (3)	C9—C7—C6	115.4 (9)
O7—Lu1—O13	72.2 (3)	O2—C8—C3	116.5 (8)
O2—Lu1—O12	119.5 (2)	O2—C8—C7	122.9 (9)
O3—Lu1—O12	167.1 (2)	C3—C8—C7	120.6 (9)
O10—Lu1—O12	69.0 (3)	N1—C9—C7	121.9 (8)
O9—Lu1—O12	112.3 (3)	N1—C9—H9	119.0
O6—Lu1—O12	67.6 (3)	C7—C9—H9	119.0
O7—Lu1—O12	96.7 (3)	N1—C10—C11	120.1 (12)
O13—Lu1—O12	48.7 (2)	N1—C10—C12	105.3 (17)
O2—Lu1—O1	61.3 (2)	C11—C10—C12	104.3 (11)
O3—Lu1—O1	121.59 (19)	N1—C10—H10	108.9
O10—Lu1—O1	82.4 (2)	C11—C10—H10	108.9
O9—Lu1—O1	75.8 (2)	C12—C10—H10	108.9
O6—Lu1—O1	80.5 (3)	N1—C10'—C11	120.9 (11)
O7—Lu1—O1	128.1 (3)	N1—C10'—C12'	107.1 (18)
O13—Lu1—O1	114.3 (2)	C11—C10'—C12'	105.2 (12)
O12—Lu1—O1	66.0 (2)	N1—C10'—H10'	107.6
O2—Lu1—O4	122.4 (2)	C11—C10'—H10'	107.6
O3—Lu1—O4	60.70 (18)	C12'—C10'—H10'	107.6
O10—Lu1—O4	75.1 (2)	C10—C11—H11A	109.5
O9—Lu1—O4	77.8 (2)	C10—C11—H11B	109.5
O6—Lu1—O4	126.9 (3)	H11A—C11—H11B	109.5
O7—Lu1—O4	79.4 (3)	C10—C11—H11C	109.5
O13—Lu1—O4	72.4 (2)	H11A—C11—H11C	109.5
O12—Lu1—O4	118.2 (2)	H11B—C11—H11C	109.5
O1—Lu1—O4	152.5 (2)	C10'—C11—H11D	109.3
O2—Cu1—O3	82.3 (3)	C10'—C11—H11E	110.2
O2—Cu1—N2	172.7 (3)	H11D—C11—H11E	109.5
O3—Cu1—N2	95.1 (3)	C10'—C11—H11F	108.9
O2—Cu1—N1	96.5 (3)	H11D—C11—H11F	109.5
O3—Cu1—N1	171.4 (3)	H11E—C11—H11F	109.5
N2—Cu1—N1	85.0 (3)	N2—C12—C10	108.2 (14)
O2—Cu1—O5	96.4 (3)	N2—C12—H12A	110.1
O3—Cu1—O5	95.7 (3)	C10—C12—H12A	110.1
N2—Cu1—O5	90.6 (3)	N2—C12—H12B	110.1
N1—Cu1—O5	92.9 (4)	C10—C12—H12B	110.1
C3—O1—C2	119.6 (8)	H12A—C12—H12B	108.4
C3—O1—Lu1	116.5 (5)	N2—C12'—C10'	107.1 (15)
C2—O1—Lu1	123.7 (6)	N2—C12'—H12C	110.3
C8—O2—Cu1	124.5 (5)	C10'—C12'—H12C	110.3
C8—O2—Lu1	127.1 (5)	N2—C12'—H12D	110.3
Cu1—O2—Lu1	108.0 (3)	C10'—C12'—H12D	110.3
C19—O3—Cu1	125.1 (6)	H12C—C12'—H12D	108.5
C19—O3—Lu1	129.2 (5)	N2—C13—C14	125.8 (9)
Cu1—O3—Lu1	105.7 (3)	N2—C13—H13	117.1
C18—O4—C20	117.2 (7)	C14—C13—H13	117.1
C18—O4—Lu1	118.2 (5)	C15—C14—C19	120.5 (9)
C20—O4—Lu1	124.6 (5)	C15—C14—C13	118.6 (9)
C22—O5—Cu1	128.7 (9)	C19—C14—C13	120.9 (9)
C22—O5—H5O	115.7	C16—C15—C14	121.0 (9)
Cu1—O5—H5O	115.7	C16—C15—H15	119.5
N3—O6—Lu1	99.5 (7)	C14—C15—H15	119.5
N3—O7—Lu1	98.9 (7)	C17—C16—C15	119.9 (9)
N4—O9—Lu1	96.7 (6)	C17—C16—H16	120.0
N4—O10—Lu1	97.9 (6)	C15—C16—H16	120.0
N5—O12—Lu1	95.8 (5)	C16—C17—C18	120.2 (9)
N5—O13—Lu1	98.4 (5)	C16—C17—H17	119.9
C9—N1—C10'	120.7 (11)	C18—C17—H17	119.9
C9—N1—C10	122.2 (10)	C19—C18—O4	114.3 (8)
C9—N1—Cu1	125.2 (6)	C19—C18—C17	120.4 (8)
C10'—N1—Cu1	111.0 (8)	O4—C18—C17	125.2 (8)
C10—N1—Cu1	111.0 (8)	O3—C19—C18	117.0 (8)
C13—N2—C12'	119.9 (13)	O3—C19—C14	125.3 (8)
C13—N2—C12	122.0 (13)	C18—C19—C14	117.7 (8)
C13—N2—Cu1	125.9 (6)	O4—C20—C21	112.5 (9)
C12'—N2—Cu1	112.7 (12)	O4—C20—H20A	109.1
C12—N2—Cu1	111.9 (12)	C21—C20—H20A	109.1
O8—N3—O7	123.8 (11)	O4—C20—H20B	109.1
O8—N3—O6	123.5 (11)	C21—C20—H20B	109.1
O7—N3—O6	112.7 (9)	H20A—C20—H20B	107.8
O11—N4—O9	126.5 (10)	C20—C21—H21A	109.5
O11—N4—O10	120.1 (10)	C20—C21—H21B	109.5
O9—N4—O10	113.4 (9)	H21A—C21—H21B	109.5
O13—N5—O12	116.7 (8)	C20—C21—H21C	109.5
O13—N5—O14	122.1 (9)	H21A—C21—H21C	109.5
O12—N5—O14	121.1 (9)	H21B—C21—H21C	109.5
C2—C1—H1A	109.5	O5—C22—H22A	109.5
C2—C1—H1B	109.5	O5—C22—H22B	109.5
H1A—C1—H1B	109.5	H22A—C22—H22B	109.5
C2—C1—H1C	109.5	O5—C22—H22C	109.5
H1A—C1—H1C	109.5	H22A—C22—H22C	109.5
H1B—C1—H1C	109.5	H22B—C22—H22C	109.5
O1—C2—C1	109.7 (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—N5	168.5 (7)
O6—Lu1—O1—C3	62.1 (6)	O4—Lu1—O12—N5	18.9 (7)
O7—Lu1—O1—C3	52.4 (7)	O2—Lu1—O13—N5	68.7 (9)
O13—Lu1—O1—C3	138.3 (6)	O3—Lu1—O13—N5	170.1 (5)
O12—Lu1—O1—C3	131.7 (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—C2	158.6 (7)	O6—Lu1—O13—N5	70.8 (6)
O3—Lu1—O1—C2	139.3 (6)	O7—Lu1—O13—N5	119.7 (6)
O10—Lu1—O1—C2	17.9 (7)	O12—Lu1—O13—N5	3.4 (5)
O9—Lu1—O1—C2	70.3 (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—C9	93.6 (9)
O4—Lu1—O1—C2	52.9 (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—C8	10.2 (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—Lu1	8.3 (3)	N2—Cu1—N1—C10	18.0 (10)
N1—Cu1—O2—Lu1	−163.1 (3)	O5—Cu1—N1—C10	−72.3 (10)
O5—Cu1—O2—Lu1	103.2 (3)	O3—Cu1—N2—C13	12.6 (9)
O3—Lu1—O2—C8	179.5 (8)	N1—Cu1—N2—C13	−176.0 (9)
O10—Lu1—O2—C8	70.3 (8)	O5—Cu1—N2—C13	−83.1 (9)
O9—Lu1—O2—C8	96.3 (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—C12	8.8 (17)
O1—Lu1—O2—C8	18.0 (7)	O5—Cu1—N2—C12	101.7 (17)
O4—Lu1—O2—C8	166.2 (7)	Lu1—O7—N3—O8	−175.4 (8)
O3—Lu1—O2—Cu1	−7.3 (3)	Lu1—O7—N3—O6	6.0 (10)
O10—Lu1—O2—Cu1	−116.5 (3)	Lu1—O6—N3—O8	175.4 (8)
O9—Lu1—O2—Cu1	−90.6 (3)	Lu1—O6—N3—O7	−6.0 (10)
O6—Lu1—O2—Cu1	104.5 (4)	Lu1—O9—N4—O11	−175.5 (11)
O7—Lu1—O2—Cu1	58.8 (4)	Lu1—O9—N4—O10	4.7 (9)
O13—Lu1—O2—Cu1	106.6 (6)	Lu1—O10—N4—O11	175.4 (10)
O12—Lu1—O2—Cu1	158.3 (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—O14	176.9 (7)
O2—Cu1—O3—C19	173.7 (8)	Lu1—O12—N5—O13	5.8 (9)
N2—Cu1—O3—C19	−13.2 (8)	Lu1—O12—N5—O14	−177.0 (7)
O5—Cu1—O3—C19	77.9 (7)	C3—O1—C2—C1	68.5 (12)
O2—Cu1—O3—Lu1	−8.1 (3)	Lu1—O1—C2—C1	−107.2 (9)
N2—Cu1—O3—Lu1	165.1 (3)	C2—O1—C3—C8	−159.1 (8)
O5—Cu1—O3—Lu1	−103.9 (3)	Lu1—O1—C3—C8	16.9 (10)
O2—Lu1—O3—C19	−174.7 (8)	C2—O1—C3—C4	20.3 (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—C19	118.0 (7)	O1—C3—C4—C5	177.7 (10)
O7—Lu1—O3—C19	80.9 (8)	C3—C4—C5—C6	4.4 (18)
O13—Lu1—O3—C19	29.9 (8)	C4—C5—C6—C7	−3.3 (19)
O12—Lu1—O3—C19	80.8 (13)	C5—C6—C7—C8	0.5 (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—C3	171.5 (6)
O2—Lu1—O3—Cu1	7.1 (3)	Lu1—O2—C8—C3	−16.4 (11)
O10—Lu1—O3—Cu1	126.7 (3)	Cu1—O2—C8—C7	−10.8 (12)
O9—Lu1—O3—Cu1	92.8 (3)	Lu1—O2—C8—C7	161.2 (7)
O6—Lu1—O3—Cu1	−60.1 (3)	C4—C3—C8—O2	178.0 (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—C7	0.4 (15)
O12—Lu1—O3—Cu1	−97.3 (10)	O1—C3—C8—C7	179.7 (8)
O1—Lu1—O3—Cu1	26.1 (4)	C9—C7—C8—O2	2.1 (16)
O4—Lu1—O3—Cu1	174.2 (4)	C6—C7—C8—O2	−176.6 (9)
O2—Lu1—O4—C18	18.9 (7)	C9—C7—C8—C3	179.6 (10)
O3—Lu1—O4—C18	5.3 (6)	C6—C7—C8—C3	1.0 (14)
O10—Lu1—O4—C18	144.2 (6)	C10'—N1—C9—C7	−161.7 (12)
O9—Lu1—O4—C18	90.9 (6)	C10—N1—C9—C7	161.1 (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—N1	5.5 (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—C11	37 (2)
O1—Lu1—O4—C18	108.1 (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—C12	154.4 (17)
O10—Lu1—O4—C20	−36.6 (7)	C10'—N1—C10—C12	57 (3)
O9—Lu1—O4—C20	−89.9 (7)	Cu1—N1—C10—C12	−39.2 (18)
O6—Lu1—O4—C20	101.1 (7)	C9—N1—C10'—C11	−41 (2)
O7—Lu1—O4—C20	111.0 (7)	C10—N1—C10'—C11	61.2 (14)
O13—Lu1—O4—C20	36.5 (7)	Cu1—N1—C10'—C11	157.5 (16)
O12—Lu1—O4—C20	19.1 (8)	C9—N1—C10'—C12'	−161.7 (16)
O1—Lu1—O4—C20	−72.7 (8)	C10—N1—C10'—C12'	−59 (3)
O2—Cu1—O5—C22	9.4 (14)	Cu1—N1—C10'—C12'	37.2 (18)
O3—Cu1—O5—C22	92.3 (13)	N1—C10'—C11—C10	−61.2 (14)
N2—Cu1—O5—C22	−172.5 (13)	C12'—C10'—C11—C10	60 (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—C10	151.7 (17)
O10—Lu1—O6—N3	125.7 (7)	C12'—N2—C12—C10	63 (6)
O9—Lu1—O6—N3	−138.7 (6)	Cu1—N2—C12—C10	−33 (3)
O7—Lu1—O6—N3	3.7 (6)	N1—C10—C12—N2	46 (3)
O13—Lu1—O6—N3	77.2 (7)	C11—C10—C12—N2	173 (2)
O12—Lu1—O6—N3	125.9 (7)	C13—N2—C12'—C10'	−160.6 (17)
O1—Lu1—O6—N3	−166.2 (7)	C12—N2—C12'—C10'	−59 (5)
O4—Lu1—O6—N3	16.7 (8)	Cu1—N2—C12'—C10'	32 (3)
O2—Lu1—O7—N3	64.6 (6)	N1—C10'—C12'—N2	−44 (3)
O3—Lu1—O7—N3	124.4 (7)	C11—C10'—C12'—N2	−174 (2)
O10—Lu1—O7—N3	−121.1 (7)	C12'—N2—C13—C14	−170 (2)
O9—Lu1—O7—N3	144.0 (6)	C12—N2—C13—C14	170 (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—C15	175.5 (10)
O12—Lu1—O7—N3	−55.6 (7)	N2—C13—C14—C19	−6.5 (16)
O1—Lu1—O7—N3	9.1 (8)	C19—C14—C15—C16	2.1 (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—N4	139.4 (6)	C15—C16—C17—C18	1.1 (15)
O10—Lu1—O9—N4	−2.9 (6)	C20—O4—C18—C19	177.2 (8)
O6—Lu1—O9—N4	−122.4 (8)	Lu1—O4—C18—C19	−3.6 (10)
O7—Lu1—O9—N4	120.7 (8)	C20—O4—C18—C17	1.7 (13)
O13—Lu1—O9—N4	15.9 (7)	Lu1—O4—C18—C17	−179.1 (7)
O12—Lu1—O9—N4	−38.1 (6)	C16—C17—C18—C19	4.3 (15)
O1—Lu1—O9—N4	−94.3 (6)	C16—C17—C18—O4	179.6 (9)
O4—Lu1—O9—N4	77.5 (6)	Cu1—O3—C19—C18	−173.2 (6)
O2—Lu1—O10—N4	36.4 (7)	Lu1—O3—C19—C18	9.0 (12)
O3—Lu1—O10—N4	−41.5 (7)	Cu1—O3—C19—C14	6.3 (13)
O9—Lu1—O10—N4	2.9 (6)	Lu1—O3—C19—C14	−171.5 (6)
O6—Lu1—O10—N4	148.2 (6)	O4—C18—C19—O3	−2.5 (12)
O7—Lu1—O10—N4	−136.5 (6)	C17—C18—C19—O3	173.2 (8)
O13—Lu1—O10—N4	−159.7 (7)	O4—C18—C19—C14	178.0 (8)
O12—Lu1—O10—N4	148.0 (7)	C17—C18—C19—C14	−6.3 (13)
O1—Lu1—O10—N4	80.8 (6)	C15—C14—C19—O3	−176.4 (9)
O4—Lu1—O10—N4	−83.2 (6)	C13—C14—C19—O3	5.7 (15)
O2—Lu1—O12—N5	−160.1 (5)	C15—C14—C19—C18	3.2 (14)
O3—Lu1—O12—N5	−62.5 (13)	C13—C14—C19—C18	−174.8 (9)
O10—Lu1—O12—N5	77.7 (6)	C18—O4—C20—C21	77.7 (10)
O9—Lu1—O12—N5	106.7 (6)	Lu1—O4—C20—C21	−101.5 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···O14^i	0.82	2.13	2.93 (1)	164

Symmetry code: (i) −x+1, y+1/2, −z+1/2.