[μ-N,N′-Bis(3-eth­oxy-2-oxidobenzyl­idene)propane-1,2-diamine](methanol)trinitratocopper(II)neodymium(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)neodymium(III)), [CuNd(C₂₁H₂₂N₂O₄)(NO₃)₃(CH₄O)], 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 (C₂₁H₂₄N₂O₄)(CH₄O)Cu unit uses the two eth­oxy and two hydr­oxy O atoms to chelate the (NO₃)₃Nd unit. The Cu^II atom exists in a square-pyramidal geometry and the Nd^III atom in a bicapped square-anti­prismatic geometry. Mol­ecules are linked by O—H...O hydrogen bonds into a linear chain along the b axis. Some C and H atoms of the Schiff base are disordered equally over two positions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.013 Å
• Disorder in main residue
• R factor = 0.052
• wR factor = 0.154
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for         O7

Author Response: This atom is connected to Nd1, which has a small Ueq.

 Also, C10 is connected to C11, a terminal methyl group.


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

Author Response: This atom is connected to Nd1, which has a small Ueq.

 Also, C10 is connected to C11, a terminal methyl group.

PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C11

Author Response: This atom is connected to Nd1, which has a small Ueq.

 Also, C10 is connected to C11, a terminal methyl group.

PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N3

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5

Author Response: This atom is connected to Nd1, which has a small Ueq.

 Also, C10 is connected to C11, a terminal methyl group.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O9

Author Response: This atom is connected to Nd1, which has a small Ueq.

 Also, C10 is connected to C11, a terminal methyl group.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O12

Author Response: This atom is connected to Nd1, which has a small Ueq.

 Also, C10 is connected to C11, a terminal methyl group.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O13

Author Response: This atom is connected to Nd1, which has a small Ueq.

 Also, C10 is connected to C11, a terminal methyl group.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12

Author Response: This atom is connected to Nd1, which has a small Ueq.

 Also, C10 is connected to C11, a terminal methyl group.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C12'

Author Response: This atom is connected to Nd1, which has a small Ueq.

 Also, C10 is connected to C11, a terminal methyl group.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Nd1
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         N4
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 ...         13

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         10

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  16 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

The isostructural lutetium compound is described in the preceding report (Sui et al., 2007).

Related literature

For the isostructural lutetium compound structure, see Sui et al. (2007).

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. Neodymium nitrate hexahydrate (0.44 g, 1 mmol) was added and then 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 1.2 Å from O6.

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 [CuNd(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.

({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)neodymium(III))

Crystal data

[CuNd(C21H22N2O4)(NO3)3(CH4O)]	F(000) = 1584
Mr = 794.27	Dx = 1.785 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8519 reflections
a = 9.2004 (4) Å	θ = 2.2–27.4°
b = 20.5069 (8) Å	µ = 2.53 mm^−1
c = 15.6901 (6) Å	T = 295 K
β = 93.111 (1)°	Block, red
V = 2955.9 (2) Å^3	0.34 × 0.13 × 0.11 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer	6644 independent reflections
Radiation source: fine-focus sealed tube	5212 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.426, Tmax = 0.768	k = −26→26
21321 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0498P)^2 + 17.0691P] where P = (Fo^2 + 2Fc^2)/3
6644 reflections	(Δ/σ)max = 0.001
395 parameters	Δρmax = 1.04 e Å^−3
10 restraints	Δρmin = −0.68 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Nd1	0.36649 (4)	0.341072 (17)	0.25006 (3)	0.04394 (13)
Cu1	0.33005 (10)	0.50577 (4)	0.29959 (6)	0.0486 (2)
O1	0.1453 (6)	0.3478 (2)	0.1359 (4)	0.0575 (14)
O2	0.2273 (6)	0.4403 (2)	0.2355 (4)	0.0578 (14)
O3	0.4766 (6)	0.4393 (2)	0.3103 (4)	0.0562 (14)
O4	0.6487 (5)	0.3420 (2)	0.2987 (4)	0.0523 (12)
O5	0.4301 (11)	0.5592 (4)	0.1838 (5)	0.118 (3)
H5O	0.4926	0.5868	0.1952	0.141*
O6	0.1577 (8)	0.3228 (5)	0.3439 (5)	0.096 (2)
O7	0.3543 (9)	0.3409 (5)	0.4117 (5)	0.105 (3)
O8	0.1590 (10)	0.3344 (3)	0.4808 (5)	0.095 (2)
O9	0.4799 (8)	0.3825 (3)	0.1171 (4)	0.0774 (18)
O10	0.4850 (8)	0.2788 (3)	0.1368 (4)	0.0755 (18)
O11	0.6037 (12)	0.3199 (5)	0.0342 (6)	0.127 (3)
O12	0.2348 (7)	0.2302 (3)	0.2231 (5)	0.0765 (19)
O13	0.4328 (7)	0.2252 (3)	0.3004 (4)	0.0702 (17)
O14	0.3190 (8)	0.1367 (3)	0.2636 (5)	0.090 (2)
N1	0.1700 (8)	0.5660 (3)	0.3028 (5)	0.066 (2)
N2	0.4296 (8)	0.5647 (3)	0.3777 (5)	0.0597 (17)
N3	0.2211 (10)	0.3338 (3)	0.4139 (5)	0.0647 (19)
N4	0.5249 (10)	0.3268 (4)	0.0932 (5)	0.076 (2)
N5	0.3294 (8)	0.1962 (3)	0.2621 (5)	0.0582 (17)
C1	0.1630 (14)	0.3442 (6)	−0.0207 (7)	0.101 (4)
H1A	0.1443	0.3168	−0.0697	0.152*
H1B	0.2632	0.3575	−0.0179	0.152*
H1C	0.1017	0.3820	−0.0254	0.152*
C2	0.1310 (11)	0.3065 (4)	0.0602 (6)	0.068 (2)
H2A	0.0330	0.2891	0.0545	0.082*
H2B	0.1979	0.2701	0.0669	0.082*
C3	0.0446 (9)	0.3977 (4)	0.1433 (5)	0.0556 (19)
C4	−0.0931 (11)	0.3986 (5)	0.1044 (7)	0.079 (3)
H4	−0.1254	0.3647	0.0688	0.095*
C5	−0.1829 (11)	0.4514 (6)	0.1196 (7)	0.084 (3)
H5	−0.2765	0.4527	0.0941	0.101*
C6	−0.1359 (10)	0.5010 (5)	0.1708 (7)	0.071 (3)
H6	−0.1992	0.5352	0.1804	0.086*
C7	0.0062 (8)	0.5027 (4)	0.2104 (6)	0.0553 (19)
C8	0.0942 (8)	0.4479 (3)	0.1983 (5)	0.0496 (17)
C9	0.0431 (11)	0.5567 (4)	0.2632 (6)	0.072 (3)
H9	−0.0284	0.5880	0.2703	0.086*
C10	0.2181 (17)	0.6309 (6)	0.3334 (14)	0.074 (5)	0.50
H10	0.2650	0.6545	0.2880	0.089*	0.50
C10'	0.195 (2)	0.6127 (7)	0.3723 (10)	0.074 (5)	0.50
H10'	0.1631	0.5889	0.4222	0.089*	0.50
C11	0.1042 (13)	0.6729 (5)	0.3711 (9)	0.108 (4)
H11A	0.1491	0.7114	0.3954	0.162*	0.50
H11B	0.0581	0.6491	0.4149	0.162*	0.50
H11C	0.0325	0.6852	0.3273	0.162*	0.50
H11D	0.0031	0.6621	0.3614	0.162*	0.50
H11E	0.1181	0.6956	0.4245	0.162*	0.50
H11F	0.1342	0.7004	0.3257	0.162*	0.50
C12	0.328 (3)	0.6143 (14)	0.405 (2)	0.096 (7)	0.50
H12A	0.3810	0.6533	0.4219	0.116*	0.50
H12B	0.2775	0.5985	0.4532	0.116*	0.50
C12'	0.353 (2)	0.6253 (11)	0.395 (3)	0.096 (7)	0.50
H12C	0.3885	0.6605	0.3599	0.116*	0.50
H12D	0.3674	0.6374	0.4542	0.116*	0.50
C13	0.5624 (10)	0.5605 (4)	0.4056 (5)	0.062 (2)
H13	0.6008	0.5944	0.4391	0.074*
C14	0.6573 (10)	0.5057 (4)	0.3882 (5)	0.058 (2)
C15	0.8015 (10)	0.5096 (4)	0.4202 (6)	0.066 (2)
H15	0.8330	0.5468	0.4497	0.079*
C16	0.8963 (10)	0.4605 (4)	0.4093 (6)	0.066 (2)
H16	0.9930	0.4652	0.4289	0.079*
C17	0.8515 (8)	0.4033 (4)	0.3693 (5)	0.0566 (19)
H17	0.9168	0.3693	0.3627	0.068*
C18	0.7074 (9)	0.3974 (4)	0.3391 (5)	0.0501 (18)
C19	0.6091 (8)	0.4481 (3)	0.3459 (5)	0.0471 (16)
C20	0.7444 (9)	0.2873 (4)	0.2865 (6)	0.063 (2)
H20A	0.8360	0.3034	0.2671	0.075*
H20B	0.7012	0.2593	0.2423	0.075*
C21	0.7736 (12)	0.2480 (5)	0.3661 (7)	0.087 (3)
H21A	0.7747	0.2025	0.3518	0.130*
H21B	0.6986	0.2561	0.4049	0.130*
H21C	0.8662	0.2602	0.3924	0.130*
C22	0.3945 (19)	0.5487 (7)	0.1005 (8)	0.131 (6)
H22A	0.4779	0.5565	0.0678	0.196*
H22B	0.3173	0.5777	0.0819	0.196*
H22C	0.3629	0.5044	0.0926	0.196*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Nd1	0.0452 (2)	0.03140 (19)	0.0547 (2)	0.00066 (16)	−0.00207 (16)	−0.00479 (16)
Cu1	0.0533 (5)	0.0312 (4)	0.0611 (6)	0.0019 (4)	0.0023 (4)	−0.0057 (4)
O1	0.059 (3)	0.046 (3)	0.066 (3)	0.000 (2)	−0.013 (3)	−0.008 (2)
O2	0.053 (3)	0.038 (3)	0.081 (4)	0.009 (2)	−0.013 (3)	−0.009 (3)
O3	0.050 (3)	0.039 (3)	0.078 (4)	0.007 (2)	−0.018 (3)	−0.015 (2)
O4	0.045 (3)	0.041 (3)	0.070 (3)	−0.002 (2)	−0.003 (2)	−0.011 (2)
O5	0.164 (9)	0.118 (7)	0.074 (5)	−0.075 (6)	0.033 (5)	−0.004 (5)
O6	0.067 (4)	0.156 (8)	0.066 (4)	0.019 (5)	0.007 (4)	0.006 (5)
O7	0.085 (6)	0.162 (9)	0.066 (4)	−0.037 (5)	−0.002 (4)	−0.010 (5)
O8	0.136 (7)	0.077 (5)	0.078 (5)	−0.009 (4)	0.045 (5)	0.002 (4)
O9	0.088 (5)	0.064 (4)	0.081 (4)	−0.002 (3)	0.017 (4)	0.012 (3)
O10	0.098 (5)	0.058 (4)	0.072 (4)	0.000 (3)	0.020 (4)	−0.008 (3)
O11	0.156 (9)	0.129 (7)	0.102 (6)	−0.027 (6)	0.074 (6)	−0.020 (5)
O12	0.064 (4)	0.049 (3)	0.114 (5)	−0.006 (3)	−0.019 (4)	0.006 (3)
O13	0.059 (4)	0.051 (3)	0.098 (5)	−0.008 (3)	−0.018 (3)	0.010 (3)
O14	0.103 (5)	0.031 (3)	0.137 (7)	−0.012 (3)	0.013 (5)	−0.002 (3)
N1	0.059 (5)	0.042 (4)	0.098 (6)	0.013 (3)	−0.001 (4)	−0.010 (4)
N2	0.071 (5)	0.042 (3)	0.067 (4)	0.001 (3)	0.002 (4)	−0.013 (3)
N3	0.090 (6)	0.042 (4)	0.063 (5)	0.000 (4)	0.017 (4)	−0.003 (3)
N4	0.083 (6)	0.082 (6)	0.063 (5)	−0.011 (5)	0.012 (4)	−0.008 (4)
N5	0.068 (5)	0.034 (3)	0.074 (5)	−0.007 (3)	0.017 (4)	−0.002 (3)
C1	0.111 (10)	0.126 (11)	0.066 (7)	−0.008 (8)	0.001 (6)	−0.001 (7)
C2	0.076 (6)	0.055 (5)	0.070 (6)	−0.001 (4)	−0.018 (5)	−0.014 (4)
C3	0.051 (5)	0.049 (4)	0.066 (5)	0.007 (3)	−0.002 (4)	0.005 (4)
C4	0.078 (7)	0.073 (6)	0.084 (7)	0.009 (5)	−0.021 (5)	0.000 (5)
C5	0.056 (6)	0.099 (8)	0.096 (8)	0.021 (6)	−0.012 (5)	0.010 (6)
C6	0.048 (5)	0.062 (5)	0.102 (7)	0.007 (4)	−0.006 (5)	0.008 (5)
C7	0.036 (4)	0.055 (5)	0.074 (5)	0.018 (3)	−0.006 (4)	0.009 (4)
C8	0.040 (4)	0.040 (4)	0.069 (5)	0.002 (3)	0.000 (3)	0.009 (3)
C9	0.078 (7)	0.051 (5)	0.089 (7)	0.027 (5)	0.023 (5)	0.004 (4)
C10	0.102 (11)	0.030 (7)	0.091 (14)	0.014 (7)	0.016 (10)	−0.004 (7)
C10'	0.102 (11)	0.030 (7)	0.091 (14)	0.014 (7)	0.016 (10)	−0.004 (7)
C11	0.100 (9)	0.075 (7)	0.151 (12)	0.020 (7)	0.013 (8)	−0.012 (7)
C12	0.072 (10)	0.065 (9)	0.149 (13)	0.015 (8)	−0.016 (9)	−0.058 (9)
C12'	0.072 (10)	0.065 (9)	0.149 (13)	0.015 (8)	−0.016 (9)	−0.058 (9)
C13	0.078 (6)	0.045 (4)	0.061 (5)	−0.007 (4)	−0.011 (4)	−0.016 (4)
C14	0.075 (6)	0.043 (4)	0.055 (4)	−0.005 (4)	−0.004 (4)	−0.002 (3)
C15	0.075 (6)	0.060 (5)	0.061 (5)	−0.024 (5)	−0.015 (4)	−0.006 (4)
C16	0.051 (5)	0.067 (6)	0.078 (6)	−0.008 (4)	−0.015 (4)	−0.006 (4)
C17	0.038 (4)	0.063 (5)	0.068 (5)	0.003 (3)	−0.005 (4)	−0.001 (4)
C18	0.058 (5)	0.045 (4)	0.047 (4)	−0.011 (3)	−0.002 (3)	−0.005 (3)
C19	0.046 (4)	0.042 (4)	0.053 (4)	−0.003 (3)	−0.004 (3)	−0.003 (3)
C20	0.050 (5)	0.055 (5)	0.082 (6)	0.011 (4)	−0.006 (4)	−0.012 (4)
C21	0.079 (7)	0.070 (6)	0.108 (8)	0.000 (5)	−0.013 (6)	0.012 (6)
C22	0.195 (17)	0.123 (11)	0.078 (8)	−0.026 (11)	0.042 (9)	0.018 (8)

Geometric parameters (Å, º)

Nd1—O1	2.641 (5)	C4—C5	1.390 (14)
Nd1—O2	2.408 (5)	C4—H4	0.93
Nd1—O3	2.424 (5)	C5—C6	1.351 (14)
Nd1—O4	2.666 (5)	C5—H5	0.93
Nd1—O6	2.511 (7)	C6—C7	1.417 (11)
Nd1—O7	2.545 (7)	C6—H6	0.93
Nd1—O9	2.530 (7)	C7—C8	1.404 (10)
Nd1—O10	2.487 (6)	C7—C9	1.414 (13)
Nd1—O12	2.600 (6)	C9—H9	0.93
Nd1—O13	2.567 (6)	C10—C11	1.504 (10)
Cu1—O2	1.899 (5)	C10—C12	1.502 (10)
Cu1—O3	1.918 (5)	C10—H10	0.98
Cu1—O5	2.351 (7)	C10'—C11	1.492 (9)
Cu1—N1	1.925 (7)	C10'—C12'	1.499 (10)
Cu1—N2	1.918 (7)	C10'—H10'	0.98
O1—C3	1.389 (9)	C11—H11A	0.96
O1—C2	1.459 (9)	C11—H11B	0.96
O2—C8	1.336 (9)	C11—H11C	0.96
O3—C19	1.326 (9)	C11—H11D	0.96
O4—C18	1.397 (8)	C11—H11E	0.96
O4—C20	1.444 (9)	C11—H11F	0.96
O5—C22	1.347 (14)	C12—H12A	0.97
O5—H5O	0.8200	C12—H12B	0.97
O6—N3	1.236 (10)	C12'—H12C	0.97
O7—N3	1.236 (10)	C12'—H12D	0.97
O8—N3	1.221 (9)	C13—C14	1.458 (12)
O9—N4	1.279 (10)	C13—H13	0.93
O10—N4	1.264 (10)	C14—C15	1.396 (12)
O11—N4	1.215 (11)	C14—C19	1.414 (10)
O12—N5	1.249 (9)	C15—C16	1.349 (13)
O13—N5	1.248 (9)	C15—H15	0.93
O14—N5	1.225 (8)	C16—C17	1.382 (12)
N1—C9	1.306 (12)	C16—H16	0.93
N1—C10'	1.460 (9)	C17—C18	1.389 (11)
N1—C10	1.474 (9)	C17—H17	0.93
N2—C13	1.278 (11)	C18—C19	1.385 (11)
N2—C12'	1.461 (10)	C20—C21	1.498 (13)
N2—C12	1.461 (10)	C20—H20A	0.97
C1—C2	1.528 (14)	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—C4	1.377 (12)	C22—H22C	0.96
C3—C8	1.404 (11)
O2—Nd1—O3	62.85 (17)	O1—C2—H2A	109.3
O2—Nd1—O10	128.1 (2)	C1—C2—H2A	109.3
O3—Nd1—O10	121.0 (2)	O1—C2—H2B	109.3
O2—Nd1—O6	76.2 (2)	C1—C2—H2B	109.3
O3—Nd1—O6	102.2 (3)	H2A—C2—H2B	107.9
O10—Nd1—O6	136.2 (3)	C4—C3—O1	125.1 (8)
O2—Nd1—O9	83.0 (2)	C4—C3—C8	121.5 (8)
O3—Nd1—O9	81.9 (2)	O1—C3—C8	113.3 (7)
O10—Nd1—O9	50.7 (2)	C3—C4—C5	118.4 (10)
O6—Nd1—O9	153.7 (2)	C3—C4—H4	120.8
O2—Nd1—O7	92.5 (3)	C5—C4—H4	120.8
O3—Nd1—O7	69.7 (2)	C6—C5—C4	120.9 (9)
O10—Nd1—O7	139.1 (3)	C6—C5—H5	119.6
O6—Nd1—O7	48.6 (2)	C4—C5—H5	119.6
O9—Nd1—O7	149.8 (2)	C5—C6—C7	122.5 (9)
O2—Nd1—O13	158.0 (2)	C5—C6—H6	118.7
O3—Nd1—O13	124.21 (18)	C7—C6—H6	118.7
O10—Nd1—O13	68.8 (2)	C8—C7—C6	116.5 (8)
O6—Nd1—O13	81.8 (3)	C8—C7—C9	125.8 (7)
O9—Nd1—O13	117.6 (2)	C6—C7—C9	117.6 (8)
O7—Nd1—O13	73.4 (3)	O2—C8—C3	116.2 (7)
O2—Nd1—O12	118.85 (19)	O2—C8—C7	123.8 (7)
O3—Nd1—O12	166.3 (2)	C3—C8—C7	120.0 (7)
O10—Nd1—O12	69.7 (2)	N1—C9—C7	124.9 (7)
O6—Nd1—O12	66.4 (3)	N1—C9—H9	117.5
O9—Nd1—O12	111.7 (2)	C7—C9—H9	117.5
O7—Nd1—O12	96.6 (3)	N1—C10—C11	116.3 (11)
O13—Nd1—O12	48.82 (19)	N1—C10—C12	102.5 (16)
O2—Nd1—O1	60.35 (17)	C11—C10—C12	106.9 (12)
O3—Nd1—O1	120.77 (16)	N1—C10—H10	110.3
O10—Nd1—O1	83.9 (2)	C11—C10—H10	110.3
O6—Nd1—O1	79.6 (2)	C12—C10—H10	110.3
O9—Nd1—O1	76.1 (2)	N1—C10'—C11	117.9 (11)
O7—Nd1—O1	127.0 (2)	N1—C10'—C12'	113.6 (16)
O13—Nd1—O1	114.73 (17)	C11—C10'—C12'	113.2 (12)
O12—Nd1—O1	66.42 (18)	N1—C10'—H10'	103.2
O2—Nd1—O4	121.74 (16)	C11—C10'—H10'	103.2
O3—Nd1—O4	60.19 (16)	C12'—C10'—H10'	103.2
O10—Nd1—O4	75.5 (2)	C10—C11—H11A	109.5
O6—Nd1—O4	126.6 (2)	C10—C11—H11B	109.5
O9—Nd1—O4	78.2 (2)	H11A—C11—H11B	109.5
O7—Nd1—O4	79.0 (2)	C10—C11—H11C	109.5
O13—Nd1—O4	72.95 (17)	H11A—C11—H11C	109.5
O12—Nd1—O4	119.37 (17)	H11B—C11—H11C	109.5
O1—Nd1—O4	153.69 (19)	C10'—C11—H11D	110.3
O2—Cu1—O3	82.6 (2)	C10'—C11—H11E	110.0
O2—Cu1—N2	172.2 (3)	H11D—C11—H11E	109.5
O3—Cu1—N2	94.7 (3)	C10'—C11—H11F	108.1
O2—Cu1—N1	96.2 (3)	H11D—C11—H11F	109.5
O3—Cu1—N1	171.4 (3)	H11E—C11—H11F	109.5
N2—Cu1—N1	85.3 (3)	N2—C12—C10	111.0 (15)
O2—Cu1—O5	97.2 (3)	N2—C12—H12A	109.4
O3—Cu1—O5	95.5 (3)	C10—C12—H12A	109.4
N2—Cu1—O5	90.4 (3)	N2—C12—H12B	109.4
N1—Cu1—O5	93.1 (4)	C10—C12—H12B	109.4
C3—O1—C2	117.7 (6)	H12A—C12—H12B	108.0
C3—O1—Nd1	118.3 (4)	N2—C12'—C10'	106.3 (14)
C2—O1—Nd1	123.7 (5)	N2—C12'—H12C	110.5
C8—O2—Cu1	124.5 (5)	C10'—C12'—H12C	110.5
C8—O2—Nd1	127.6 (4)	N2—C12'—H12D	110.5
Cu1—O2—Nd1	107.5 (2)	C10'—C12'—H12D	110.5
C19—O3—Cu1	124.5 (4)	H12C—C12'—H12D	108.7
C19—O3—Nd1	129.2 (4)	N2—C13—C14	124.0 (7)
Cu1—O3—Nd1	106.2 (2)	N2—C13—H13	118.0
C18—O4—C20	117.9 (6)	C14—C13—H13	118.0
C18—O4—Nd1	118.8 (4)	C15—C14—C19	119.0 (8)
C20—O4—Nd1	123.2 (4)	C15—C14—C13	117.1 (7)
C22—O5—Cu1	126.2 (8)	C19—C14—C13	123.8 (8)
C22—O5—H5O	116.9	C16—C15—C14	121.3 (8)
Cu1—O5—H5O	116.9	C16—C15—H15	119.3
N3—O6—Nd1	98.9 (6)	C14—C15—H15	119.3
N3—O7—Nd1	97.2 (5)	C15—C16—C17	120.8 (8)
N4—O9—Nd1	95.5 (5)	C15—C16—H16	119.6
N4—O10—Nd1	98.0 (5)	C17—C16—H16	119.6
N5—O12—Nd1	95.8 (4)	C16—C17—C18	119.0 (8)
N5—O13—Nd1	97.5 (4)	C16—C17—H17	120.5
C9—N1—C10'	123.5 (10)	C18—C17—H17	120.5
C9—N1—C10	122.1 (10)	C19—C18—C17	121.6 (7)
C9—N1—Cu1	124.0 (6)	C19—C18—O4	114.1 (6)
C10'—N1—Cu1	110.5 (7)	C17—C18—O4	124.3 (7)
C10—N1—Cu1	111.8 (7)	O3—C19—C18	117.1 (6)
C13—N2—C12'	117.2 (11)	O3—C19—C14	124.7 (7)
C13—N2—C12	124.4 (12)	C18—C19—C14	118.3 (7)
C13—N2—Cu1	126.2 (5)	O4—C20—C21	113.0 (8)
C12'—N2—Cu1	115.7 (11)	O4—C20—H20A	109.0
C12—N2—Cu1	109.3 (11)	C21—C20—H20A	109.0
O8—N3—O7	122.2 (9)	O4—C20—H20B	109.0
O8—N3—O6	123.0 (9)	C21—C20—H20B	109.0
O7—N3—O6	114.7 (8)	H20A—C20—H20B	107.8
O11—N4—O10	121.7 (9)	C20—C21—H21A	109.5
O11—N4—O9	123.0 (9)	C20—C21—H21B	109.5
O10—N4—O9	115.3 (8)	H21A—C21—H21B	109.5
O14—N5—O13	121.6 (8)	C20—C21—H21C	109.5
O14—N5—O12	120.8 (8)	H21A—C21—H21C	109.5
O13—N5—O12	117.6 (6)	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	111.7 (8)
O2—Nd1—O1—C3	−16.6 (5)	O6—Nd1—O12—N5	−103.0 (5)
O3—Nd1—O1—C3	−34.8 (6)	O9—Nd1—O12—N5	105.4 (5)
O10—Nd1—O1—C3	−157.5 (6)	O7—Nd1—O12—N5	−64.0 (5)
O6—Nd1—O1—C3	63.3 (6)	O13—Nd1—O12—N5	−2.9 (5)
O9—Nd1—O1—C3	−106.5 (6)	O1—Nd1—O12—N5	168.4 (6)
O7—Nd1—O1—C3	51.9 (6)	O4—Nd1—O12—N5	17.1 (6)
O13—Nd1—O1—C3	139.3 (5)	O2—Nd1—O13—N5	65.8 (8)
O12—Nd1—O1—C3	132.0 (6)	O3—Nd1—O13—N5	168.0 (4)
O4—Nd1—O1—C3	−119.0 (6)	O10—Nd1—O13—N5	−78.2 (5)
O2—Nd1—O1—C2	156.5 (7)	O6—Nd1—O13—N5	68.7 (5)
O3—Nd1—O1—C2	138.3 (6)	O9—Nd1—O13—N5	−92.6 (5)
O10—Nd1—O1—C2	15.6 (6)	O7—Nd1—O13—N5	117.8 (5)
O6—Nd1—O1—C2	−123.6 (6)	O12—Nd1—O13—N5	2.9 (5)
O9—Nd1—O1—C2	66.6 (6)	O1—Nd1—O13—N5	−5.9 (6)
O7—Nd1—O1—C2	−135.0 (6)	O4—Nd1—O13—N5	−158.9 (5)
O13—Nd1—O1—C2	−47.7 (6)	O2—Cu1—N1—C9	−4.2 (8)
O12—Nd1—O1—C2	−54.9 (6)	N2—Cu1—N1—C9	−176.5 (8)
O4—Nd1—O1—C2	54.1 (7)	O5—Cu1—N1—C9	93.3 (8)
O3—Cu1—O2—C8	−179.4 (7)	O2—Cu1—N1—C10'	160.1 (11)
N1—Cu1—O2—C8	9.1 (7)	N2—Cu1—N1—C10'	−12.2 (11)
O5—Cu1—O2—C8	−84.8 (7)	O5—Cu1—N1—C10'	−102.4 (11)
O3—Cu1—O2—Nd1	7.6 (3)	O2—Cu1—N1—C10	−167.9 (10)
N1—Cu1—O2—Nd1	−163.9 (3)	N2—Cu1—N1—C10	19.8 (11)
O5—Cu1—O2—Nd1	102.3 (3)	O5—Cu1—N1—C10	−70.3 (11)
O3—Nd1—O2—C8	−179.4 (7)	O3—Cu1—N2—C13	13.7 (8)
O10—Nd1—O2—C8	71.1 (7)	N1—Cu1—N2—C13	−174.8 (8)
O6—Nd1—O2—C8	−67.6 (6)	O5—Cu1—N2—C13	−81.8 (8)
O9—Nd1—O2—C8	96.1 (6)	O3—Cu1—N2—C12	−163.5 (17)
O7—Nd1—O2—C8	−113.8 (6)	N1—Cu1—N2—C12	7.9 (17)
O13—Nd1—O2—C8	−64.7 (9)	O5—Cu1—N2—C12	101.0 (17)
O12—Nd1—O2—C8	−14.8 (7)	Nd1—O7—N3—O8	−175.8 (7)
O1—Nd1—O2—C8	18.1 (6)	Nd1—O7—N3—O6	7.7 (9)
O4—Nd1—O2—C8	167.5 (6)	Nd1—O6—N3—O8	175.7 (7)
O3—Nd1—O2—Cu1	−6.7 (2)	Nd1—O6—N3—O7	−7.8 (9)
O10—Nd1—O2—Cu1	−116.2 (3)	Nd1—O10—N4—O11	171.8 (9)
O6—Nd1—O2—Cu1	105.1 (3)	Nd1—O10—N4—O9	−6.4 (9)
O9—Nd1—O2—Cu1	−91.2 (3)	Nd1—O9—N4—O11	−171.9 (10)
O7—Nd1—O2—Cu1	58.9 (3)	Nd1—O9—N4—O10	6.2 (9)
O13—Nd1—O2—Cu1	108.0 (5)	Nd1—O13—N5—O14	176.1 (7)
O12—Nd1—O2—Cu1	157.9 (3)	Nd1—O13—N5—O12	−5.2 (8)
O1—Nd1—O2—Cu1	−169.2 (4)	Nd1—O12—N5—O14	−176.2 (7)
O4—Nd1—O2—Cu1	−19.8 (4)	Nd1—O12—N5—O13	5.1 (8)
O2—Cu1—O3—C19	173.7 (7)	C3—O1—C2—C1	67.5 (11)
N2—Cu1—O3—C19	−13.7 (7)	Nd1—O1—C2—C1	−105.7 (8)
O5—Cu1—O3—C19	77.2 (6)	C2—O1—C3—C4	24.3 (13)
O2—Cu1—O3—Nd1	−7.5 (3)	Nd1—O1—C3—C4	−162.2 (8)
N2—Cu1—O3—Nd1	165.1 (3)	C2—O1—C3—C8	−158.0 (7)
O5—Cu1—O3—Nd1	−104.1 (3)	Nd1—O1—C3—C8	15.5 (9)
O2—Nd1—O3—C19	−174.7 (7)	O1—C3—C4—C5	178.5 (9)
O10—Nd1—O3—C19	−54.6 (7)	C8—C3—C4—C5	1.0 (15)
O6—Nd1—O3—C19	117.9 (7)	C3—C4—C5—C6	0.5 (17)
O9—Nd1—O3—C19	−88.4 (7)	C4—C5—C6—C7	1.1 (17)
O7—Nd1—O3—C19	81.3 (7)	C5—C6—C7—C8	−4.0 (15)
O13—Nd1—O3—C19	29.6 (7)	C5—C6—C7—C9	−179.5 (10)
O12—Nd1—O3—C19	84.6 (10)	Cu1—O2—C8—C3	170.9 (6)
O1—Nd1—O3—C19	−156.9 (6)	Nd1—O2—C8—C3	−17.5 (10)
O4—Nd1—O3—C19	−7.5 (6)	Cu1—O2—C8—C7	−8.0 (11)
O2—Nd1—O3—Cu1	6.6 (2)	Nd1—O2—C8—C7	163.6 (6)
O10—Nd1—O3—Cu1	126.7 (3)	C4—C3—C8—O2	177.0 (8)
O6—Nd1—O3—Cu1	−60.8 (3)	O1—C3—C8—O2	−0.8 (10)
O9—Nd1—O3—Cu1	92.9 (3)	C4—C3—C8—C7	−4.1 (13)
O7—Nd1—O3—Cu1	−97.4 (3)	O1—C3—C8—C7	178.2 (7)
O13—Nd1—O3—Cu1	−149.1 (2)	C6—C7—C8—O2	−175.8 (8)
O12—Nd1—O3—Cu1	−94.1 (8)	C9—C7—C8—O2	−0.7 (14)
O1—Nd1—O3—Cu1	24.4 (4)	C6—C7—C8—C3	5.3 (12)
O4—Nd1—O3—Cu1	173.8 (3)	C9—C7—C8—C3	−179.5 (9)
O2—Nd1—O4—C18	18.1 (6)	C10'—N1—C9—C7	−164.5 (12)
O3—Nd1—O4—C18	4.7 (5)	C10—N1—C9—C7	159.9 (12)
O10—Nd1—O4—C18	144.3 (5)	Cu1—N1—C9—C7	−2.2 (14)
O6—Nd1—O4—C18	−78.3 (6)	C8—C7—C9—N1	6.2 (16)
O9—Nd1—O4—C18	92.2 (5)	C6—C7—C9—N1	−178.7 (9)
O7—Nd1—O4—C18	−68.0 (5)	C9—N1—C10—C11	39 (2)
O13—Nd1—O4—C18	−143.9 (5)	C10'—N1—C10—C11	−63.2 (14)
O12—Nd1—O4—C18	−159.5 (5)	Cu1—N1—C10—C11	−156.7 (13)
O1—Nd1—O4—C18	104.6 (6)	C9—N1—C10—C12	155.4 (16)
O2—Nd1—O4—C20	−162.8 (6)	C10'—N1—C10—C12	53 (2)
O3—Nd1—O4—C20	−176.2 (6)	Cu1—N1—C10—C12	−40.5 (16)
O10—Nd1—O4—C20	−36.6 (6)	C9—N1—C10'—C11	−31 (2)
O6—Nd1—O4—C20	100.8 (6)	C10—N1—C10'—C11	65.9 (14)
O9—Nd1—O4—C20	−88.7 (6)	Cu1—N1—C10'—C11	164.2 (14)
O7—Nd1—O4—C20	111.1 (6)	C9—N1—C10'—C12'	−167.3 (19)
O13—Nd1—O4—C20	35.2 (6)	C10—N1—C10'—C12'	−70 (3)
O12—Nd1—O4—C20	19.6 (7)	Cu1—N1—C10'—C12'	28 (2)
O1—Nd1—O4—C20	−76.3 (7)	N1—C10'—C11—C10	−65.8 (15)
O2—Cu1—O5—C22	10.2 (12)	C12'—C10'—C11—C10	70 (3)
O3—Cu1—O5—C22	93.4 (12)	N1—C10—C11—C10'	62.9 (14)
N2—Cu1—O5—C22	−171.8 (12)	C12—C10—C11—C10'	−51 (3)
N1—Cu1—O5—C22	−86.4 (12)	C13—N2—C12—C10	148.7 (17)
O2—Nd1—O6—N3	−101.4 (6)	C12'—N2—C12—C10	85 (9)
O3—Nd1—O6—N3	−43.7 (6)	Cu1—N2—C12—C10	−34 (3)
O10—Nd1—O6—N3	127.1 (6)	N1—C10—C12—N2	48 (3)
O9—Nd1—O6—N3	−140.3 (5)	C11—C10—C12—N2	170 (2)
O7—Nd1—O6—N3	4.6 (5)	C13—N2—C12'—C10'	−168.5 (18)
O13—Nd1—O6—N3	79.7 (6)	C12—N2—C12'—C10'	−45 (7)
O12—Nd1—O6—N3	128.1 (6)	Cu1—N2—C12'—C10'	22 (3)
O1—Nd1—O6—N3	−163.2 (6)	N1—C10'—C12'—N2	−32 (3)
O4—Nd1—O6—N3	18.1 (7)	C11—C10'—C12'—N2	−169.8 (19)
O2—Nd1—O7—N3	64.6 (6)	C12'—N2—C13—C14	−175 (2)
O3—Nd1—O7—N3	124.3 (7)	C12—N2—C13—C14	171 (2)
O10—Nd1—O7—N3	−121.4 (6)	Cu1—N2—C13—C14	−6.1 (13)
O6—Nd1—O7—N3	−4.6 (5)	N2—C13—C14—C15	177.3 (9)
O9—Nd1—O7—N3	145.0 (5)	N2—C13—C14—C19	−6.6 (14)
O13—Nd1—O7—N3	−98.3 (6)	C19—C14—C15—C16	2.0 (13)
O12—Nd1—O7—N3	−54.9 (6)	C13—C14—C15—C16	178.2 (9)
O1—Nd1—O7—N3	10.5 (7)	C14—C15—C16—C17	−3.0 (15)
O4—Nd1—O7—N3	−173.6 (6)	C15—C16—C17—C18	1.0 (14)
O2—Nd1—O9—N4	−158.2 (6)	C16—C17—C18—C19	2.0 (13)
O3—Nd1—O9—N4	138.3 (6)	C16—C17—C18—O4	−179.1 (8)
O10—Nd1—O9—N4	−3.7 (5)	C20—O4—C18—C19	178.2 (7)
O6—Nd1—O9—N4	−120.3 (7)	Nd1—O4—C18—C19	−2.7 (8)
O7—Nd1—O9—N4	118.8 (7)	C20—O4—C18—C17	−0.8 (11)
O13—Nd1—O9—N4	13.8 (6)	Nd1—O4—C18—C17	178.3 (6)
O12—Nd1—O9—N4	−39.9 (6)	Cu1—O3—C19—C18	−172.3 (5)
O1—Nd1—O9—N4	−97.1 (6)	Nd1—O3—C19—C18	9.2 (10)
O4—Nd1—O9—N4	77.2 (5)	Cu1—O3—C19—C14	6.4 (11)
O2—Nd1—O10—N4	36.6 (7)	Nd1—O3—C19—C14	−172.1 (6)
O3—Nd1—O10—N4	−41.6 (6)	C17—C18—C19—O3	175.8 (7)
O6—Nd1—O10—N4	148.9 (5)	O4—C18—C19—O3	−3.3 (10)
O9—Nd1—O10—N4	3.7 (5)	C17—C18—C19—C14	−2.9 (12)
O7—Nd1—O10—N4	−135.9 (6)	O4—C18—C19—C14	178.0 (7)
O13—Nd1—O10—N4	−159.7 (6)	C15—C14—C19—O3	−177.6 (8)
O12—Nd1—O10—N4	147.9 (6)	C13—C14—C19—O3	6.4 (13)
O1—Nd1—O10—N4	80.8 (6)	C15—C14—C19—C18	1.0 (12)
O4—Nd1—O10—N4	−82.7 (6)	C13—C14—C19—C18	−175.0 (8)
O2—Nd1—O12—N5	−160.6 (5)	C18—O4—C20—C21	78.0 (9)
O3—Nd1—O12—N5	−67.2 (10)	Nd1—O4—C20—C21	−101.1 (7)
O10—Nd1—O12—N5	76.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···O14^i	0.82	2.08	2.89 (1)	165

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