[μ-N,N′-Bis(3-meth­oxy-2-oxidobenzyl­idene)propane-1,3-diamine]trinitratocopper(II)terbium(III) acetone solvate

Fei, L.; Fang, Z.

doi:10.1107/S1600536808002080

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m406

doi:10.1107/S1600536808002080

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[μ-N,N′-Bis(3-methoxy-2-oxidobenzylidene)propane-1,3-diamine]trinitratocopper(II)terbium(III) acetone solvate

Liu Fei ^a ^* and Zhang Fang ^a

^aThe College of Chemical Engineering & Materials, Eastern Liaoning University, 325 Wenhua Road, Yuanbao District, Dandong City, Liaoning Province 118003, People's Republic of China
^*Correspondence e-mail: berylliu8090@sina.com

(Received 19 December 2007; accepted 21 January 2008; online 25 January 2008)

In the title complex, [CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃]·CH₃COCH₃, the Cu^II atom is four-coordinated by two O atoms and two N atoms from the deprotonated Schiff base in a square-planar geometry, while the Tb^III atom is ten-coordinated by four O atoms from the deprotonated Schiff base and six O atoms from three bidentate nitrate anions. The compound is isostructural with the previously reported Gd^III analogue [Elmali & Elerman (2004 ). Z. Naturforsch. Teil B, 59, 535–540], which was described in the space group P1 with two formula units in the asymmetric unit. The crystal stucture is, in fact, centrosymmetric and is described here in the space group P $[\overline{1}]$ with one formula unit in the asymmetric unit.

Related literature

For the isostructural Gd^III complex, see: Elmali & Elerman (2004). For a similar copper–cerium complex, see: Elmali & Elerman (2003 ).

Experimental

Crystal data

[CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃]·C₃H₆O
M_r = 806.94
Triclinic, $[P \overline 1]$
a = 9.388 (5) Å
b = 12.108 (6) Å
c = 13.604 (6) Å
α = 73.079 (16)°
β = 86.67 (2)°
γ = 72.33 (2)°
V = 1408.8 (12) Å³
Z = 2
Mo Kα radiation
μ = 3.32 mm⁻¹
T = 291 (2) K
0.19 × 0.16 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.569, T_max = 0.659
12171 measured reflections
6275 independent reflections
5621 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.083
S = 1.11
6275 reflections
392 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu2—O1	1.939 (3)
Cu2—O3	1.947 (2)
Cu2—N2	1.957 (3)
Cu2—N1	1.989 (3)
O1—Tb1	2.352 (2)
O2—Tb1	2.506 (3)
O3—Tb1	2.344 (3)
O4—Tb1	2.492 (2)
O5—Tb1	2.470 (3)
O7—Tb1	2.501 (3)
O8—Tb1	2.455 (3)
O10—Tb1	2.494 (3)
O11—Tb1	2.491 (3)
O13—Tb1	2.564 (3)

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002080/bi2275sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002080/bi2275Isup2.hkl

checkCIF report

Comment top

As shown in Fig. 1, the hexadentate Schiff base ligand links the Cu^II and Tb^II atoms into a dinuclear complex through two phenolate O atoms. The Tb^III atom is ten-coordinated by four O atoms from the ligand and six O atoms from three nitrate anions. The Cu^II atom is four-coordinated by two N atoms and two O atoms from the ligand. The acetone molecule is not associated with the complex. The complex is isostructural with its Gd^III analogue (Elmali & Elerman, 2004), although that was refined in space group P1 with two independent complexes in the asymmetric unit. A similar compound with Ce^III has also been reported (Elmali & Elerman, 2003).

Related literature top

For the isostructural Gd^III complex, see: Elmali & Elerman (2004). For a similar copper–cerium complex, see: Elmali & Elerman (2003).

Experimental top

The title complex was obtained by reaction of copper(II) acetate monohydrate (0.05 g, 0.25 mmol) with the Schiff base (0.0855 g, 0.25 mmol) in methanol/acetone (20 ml:5 ml). Terbium (III) nitrate hexahydrate (0.1126 g, 0.25 mmol) was added and the mixture was refluxed for 3 h. The mixture was then cooled and filtered, and diethyl ether was allowed to diffuse slowly into the filtrate. Single crystals were obtained after several days. Elemental analysis calculated: C 32.65, H 3.29, N 8.67; found: C 32.75, H 3.25, N 8.68.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure, showing 40% probability displacement ellipsoids for non-H atoms. The acetone solvent molecule is not shown.

[µ-N,N'-Bis(3-methoxy-2-oxidobenzylidene)propane-1,3- diamine]trinitratocopper(II)terbium(III) acetone solvate top

Crystal data top

[CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃]·C₃H₆O	Z = 2
M_r = 806.94	F(000) = 798
Triclinic, P1	D_x = 1.902 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.388 (5) Å	Cell parameters from 11368 reflections
b = 12.108 (6) Å	θ = 3.2–27.5°
c = 13.604 (6) Å	µ = 3.32 mm⁻¹
α = 73.079 (16)°	T = 291 K
β = 86.67 (2)°	Block, green
γ = 72.33 (2)°	0.19 × 0.16 × 0.14 mm
V = 1408.8 (12) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	6275 independent reflections
Radiation source: fine-focus sealed tube	5621 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.569, T_max = 0.659	k = −15→14
12171 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0525P)²] where P = (F_o² + 2F_c²)/3
6275 reflections	(Δ/σ)_max = 0.049
392 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃]·C₃H₆O	γ = 72.33 (2)°
M_r = 806.94	V = 1408.8 (12) Å³
Triclinic, P1	Z = 2
a = 9.388 (5) Å	Mo Kα radiation
b = 12.108 (6) Å	µ = 3.32 mm⁻¹
c = 13.604 (6) Å	T = 291 K
α = 73.079 (16)°	0.19 × 0.16 × 0.14 mm
β = 86.67 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	6275 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5621 reflections with I > 2σ(I)
T_min = 0.569, T_max = 0.659	R_int = 0.025
12171 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.11	Δρ_max = 0.74 e Å⁻³
6275 reflections	Δρ_min = −0.50 e Å⁻³
392 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.5484 (3)	0.7337 (3)	0.4160 (3)	0.0363 (7)
C2	0.6382 (4)	0.7732 (3)	0.3361 (3)	0.0355 (7)
C3	0.7913 (4)	0.7362 (3)	0.3494 (3)	0.0442 (8)
H1	0.8502	0.7633	0.2961	0.053*
C4	0.8589 (4)	0.6565 (4)	0.4446 (4)	0.0527 (10)
H2	0.9624	0.6320	0.4537	0.063*
C5	0.7741 (4)	0.6157 (3)	0.5227 (3)	0.0508 (10)
H3	0.8202	0.5619	0.5842	0.061*
C6	0.6164 (4)	0.6543 (3)	0.5113 (3)	0.0421 (8)
C7	0.5320 (4)	0.6050 (3)	0.5939 (3)	0.0482 (9)
H4	0.5879	0.5473	0.6503	0.058*
C8	0.3378 (6)	0.5605 (5)	0.6968 (3)	0.0765 (15)
H5	0.3421	0.5970	0.7508	0.092*
H6	0.4050	0.4785	0.7172	0.092*
C9	0.1832 (6)	0.5563 (4)	0.6869 (4)	0.0644 (12)
H8	0.1638	0.4954	0.7459	0.077*
H7	0.1742	0.5325	0.6259	0.077*
C10	0.0688 (5)	0.6752 (4)	0.6798 (3)	0.0515 (9)
H9	−0.0289	0.6632	0.6933	0.062*
H10	0.0918	0.7081	0.7318	0.062*
C11	−0.0654 (4)	0.8417 (3)	0.5466 (3)	0.0411 (7)
H11	−0.1404	0.8382	0.5941	0.049*
C12	−0.1088 (4)	0.9332 (3)	0.4497 (3)	0.0381 (7)
C13	−0.2582 (4)	1.0089 (4)	0.4359 (3)	0.0467 (8)
H12	−0.3229	1.0025	0.4903	0.056*
C14	−0.3085 (4)	1.0922 (4)	0.3422 (3)	0.0517 (9)
H13	−0.4075	1.1409	0.3338	0.062*
C15	−0.2132 (4)	1.1044 (3)	0.2598 (3)	0.0445 (8)
H14	−0.2484	1.1608	0.1968	0.053*
C16	−0.0665 (4)	1.0325 (3)	0.2724 (2)	0.0350 (6)
C17	−0.0123 (3)	0.9448 (3)	0.3682 (2)	0.0325 (6)
C18	−0.0137 (5)	1.1106 (4)	0.0937 (3)	0.0528 (9)
H15	−0.0872	1.0826	0.0705	0.079*
H16	0.0692	1.1047	0.0487	0.079*
H17	−0.0574	1.1934	0.0934	0.079*
C19	0.6458 (5)	0.8876 (4)	0.1589 (3)	0.0559 (10)
H18	0.7078	0.9296	0.1766	0.084*
H19	0.5788	0.9410	0.1026	0.084*
H20	0.7076	0.8187	0.1393	0.084*
C20	0.1948 (9)	0.3899 (6)	−0.0076 (6)	0.105 (2)
H24	0.1539	0.4022	−0.0743	0.158*
H25	0.1212	0.3778	0.0431	0.158*
H26	0.2814	0.3199	0.0078	0.158*
C21	0.2373 (7)	0.4967 (4)	−0.0065 (4)	0.0723 (14)
C22	0.3355 (8)	0.4820 (5)	0.0826 (5)	0.0892 (17)
H21	0.3467	0.5590	0.0801	0.134*
H22	0.4319	0.4262	0.0789	0.134*
H23	0.2906	0.4515	0.1459	0.134*
Cu2	0.24442 (4)	0.75725 (3)	0.49586 (3)	0.03510 (10)
N1	0.3899 (4)	0.6295 (3)	0.6009 (2)	0.0473 (7)
N2	0.0640 (3)	0.7635 (3)	0.5764 (2)	0.0388 (6)
N3	0.3245 (4)	1.1092 (3)	0.2292 (3)	0.0481 (7)
N4	0.3809 (3)	0.8115 (3)	0.0469 (3)	0.0479 (7)
N5	0.1404 (4)	0.6928 (3)	0.2358 (3)	0.0500 (7)
O1	0.4010 (3)	0.7715 (2)	0.39786 (18)	0.0432 (5)
O2	0.5608 (3)	0.8481 (2)	0.24596 (19)	0.0437 (5)
O3	0.1291 (2)	0.8745 (2)	0.37547 (17)	0.0392 (5)
O4	0.0382 (3)	1.0369 (2)	0.19704 (18)	0.0426 (5)
O5	0.3132 (3)	1.0309 (3)	0.3128 (2)	0.0533 (6)
O6	0.3324 (4)	1.2069 (3)	0.2294 (3)	0.0737 (10)
O7	0.3240 (3)	1.0788 (2)	0.1473 (2)	0.0492 (6)
O8	0.3023 (3)	0.9175 (2)	0.0474 (2)	0.0493 (6)
O9	0.4110 (4)	0.7857 (3)	−0.0338 (3)	0.0720 (9)
O10	0.4244 (3)	0.7372 (2)	0.1352 (2)	0.0505 (6)
O11	0.0991 (3)	0.7990 (2)	0.1769 (2)	0.0533 (6)
O12	0.0819 (4)	0.6173 (3)	0.2310 (3)	0.0802 (11)
O13	0.2473 (4)	0.6682 (2)	0.3006 (2)	0.0574 (7)
O14	0.2026 (6)	0.5872 (4)	−0.0747 (3)	0.1106 (16)
Tb1	0.285531 (15)	0.877969 (12)	0.234617 (10)	0.03350 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0339 (15)	0.0339 (15)	0.0403 (17)	−0.0059 (12)	−0.0049 (13)	−0.0129 (13)
C2	0.0362 (15)	0.0292 (14)	0.0398 (17)	−0.0085 (12)	−0.0044 (13)	−0.0084 (13)
C3	0.0336 (16)	0.0386 (17)	0.063 (2)	−0.0112 (13)	−0.0018 (15)	−0.0174 (17)
C4	0.0353 (17)	0.051 (2)	0.072 (3)	−0.0046 (15)	−0.0165 (18)	−0.024 (2)
C5	0.046 (2)	0.0437 (19)	0.055 (2)	0.0031 (15)	−0.0219 (18)	−0.0149 (17)
C6	0.0411 (18)	0.0354 (16)	0.0444 (19)	0.0003 (13)	−0.0121 (15)	−0.0131 (15)
C7	0.056 (2)	0.0387 (18)	0.0319 (17)	0.0081 (15)	−0.0086 (16)	−0.0043 (14)
C8	0.077 (3)	0.066 (3)	0.040 (2)	0.009 (2)	0.010 (2)	0.022 (2)
C9	0.105 (4)	0.0377 (19)	0.048 (2)	−0.027 (2)	0.012 (2)	−0.0054 (17)
C10	0.057 (2)	0.060 (2)	0.0343 (18)	−0.0255 (19)	0.0065 (16)	−0.0008 (17)
C11	0.0421 (17)	0.0494 (19)	0.0397 (18)	−0.0193 (15)	0.0100 (14)	−0.0205 (16)
C12	0.0357 (16)	0.0404 (16)	0.0441 (18)	−0.0139 (13)	0.0031 (13)	−0.0187 (15)
C13	0.0377 (17)	0.057 (2)	0.053 (2)	−0.0160 (16)	0.0086 (15)	−0.0263 (18)
C14	0.0327 (17)	0.057 (2)	0.065 (2)	0.0007 (15)	−0.0070 (17)	−0.029 (2)
C15	0.0382 (17)	0.0423 (18)	0.051 (2)	−0.0019 (14)	−0.0113 (15)	−0.0180 (16)
C16	0.0363 (15)	0.0312 (14)	0.0363 (16)	−0.0056 (12)	−0.0046 (13)	−0.0118 (13)
C17	0.0304 (14)	0.0309 (14)	0.0371 (16)	−0.0090 (11)	−0.0020 (12)	−0.0107 (13)
C18	0.056 (2)	0.047 (2)	0.0378 (19)	0.0001 (17)	−0.0110 (17)	0.0009 (16)
C19	0.047 (2)	0.065 (2)	0.052 (2)	−0.0237 (19)	0.0100 (17)	−0.006 (2)
C20	0.127 (6)	0.070 (4)	0.099 (5)	−0.021 (4)	−0.041 (4)	0.004 (3)
C21	0.093 (4)	0.049 (2)	0.056 (3)	−0.006 (2)	0.018 (3)	−0.008 (2)
C22	0.124 (5)	0.057 (3)	0.080 (4)	−0.021 (3)	0.001 (4)	−0.017 (3)
Cu2	0.0369 (2)	0.03297 (19)	0.02827 (19)	−0.00746 (16)	0.00002 (15)	−0.00112 (16)
N1	0.0553 (18)	0.0390 (15)	0.0307 (14)	0.0011 (13)	0.0008 (13)	−0.0005 (12)
N2	0.0462 (15)	0.0427 (15)	0.0307 (14)	−0.0200 (13)	0.0034 (12)	−0.0085 (12)
N3	0.0469 (17)	0.0448 (17)	0.0512 (19)	−0.0138 (14)	−0.0015 (14)	−0.0113 (15)
N4	0.0419 (16)	0.0621 (19)	0.0450 (17)	−0.0191 (15)	0.0063 (13)	−0.0205 (16)
N5	0.0483 (17)	0.0406 (16)	0.060 (2)	−0.0183 (14)	0.0202 (15)	−0.0117 (15)
O1	0.0304 (11)	0.0507 (14)	0.0324 (11)	−0.0035 (10)	−0.0023 (9)	0.0036 (10)
O2	0.0343 (12)	0.0521 (14)	0.0374 (13)	−0.0126 (11)	0.0025 (10)	−0.0025 (11)
O3	0.0319 (11)	0.0414 (12)	0.0307 (11)	−0.0015 (9)	0.0007 (9)	0.0001 (10)
O4	0.0387 (12)	0.0368 (12)	0.0369 (12)	0.0031 (10)	−0.0076 (10)	−0.0011 (10)
O5	0.0615 (17)	0.0517 (15)	0.0443 (14)	−0.0160 (13)	0.0051 (12)	−0.0118 (13)
O6	0.095 (3)	0.0440 (16)	0.084 (2)	−0.0250 (16)	−0.011 (2)	−0.0140 (16)
O7	0.0602 (16)	0.0467 (14)	0.0375 (13)	−0.0200 (12)	0.0008 (12)	−0.0030 (11)
O8	0.0596 (16)	0.0458 (14)	0.0369 (13)	−0.0136 (12)	0.0043 (11)	−0.0065 (11)
O9	0.075 (2)	0.093 (2)	0.0543 (18)	−0.0167 (18)	0.0059 (16)	−0.0401 (18)
O10	0.0519 (15)	0.0448 (14)	0.0441 (14)	−0.0038 (11)	−0.0027 (12)	−0.0073 (12)
O11	0.0455 (14)	0.0491 (15)	0.0627 (17)	−0.0158 (12)	0.0011 (13)	−0.0104 (13)
O12	0.079 (2)	0.070 (2)	0.115 (3)	−0.0458 (19)	0.034 (2)	−0.042 (2)
O13	0.0661 (18)	0.0377 (13)	0.0569 (17)	−0.0112 (13)	0.0044 (14)	−0.0016 (12)
O14	0.157 (5)	0.065 (2)	0.077 (3)	−0.011 (3)	0.008 (3)	0.004 (2)
Tb1	0.03237 (9)	0.03267 (9)	0.02717 (9)	−0.00535 (6)	−0.00082 (6)	−0.00045 (6)

Geometric parameters (Å, º) top

C1—O1	1.332 (4)	C18—H16	0.960
C1—C2	1.399 (5)	C18—H17	0.960
C1—C6	1.418 (5)	C19—O2	1.435 (5)
C2—C3	1.375 (4)	C19—H18	0.960
C2—O2	1.382 (4)	C19—H19	0.960
C3—C4	1.417 (6)	C19—H20	0.960
C3—H1	0.930	C20—C21	1.469 (8)
C4—C5	1.357 (6)	C20—H24	0.960
C4—H2	0.930	C20—H25	0.960
C5—C6	1.414 (5)	C20—H26	0.960
C5—H3	0.930	C21—O14	1.181 (6)
C6—C7	1.428 (6)	C21—C22	1.502 (8)
C7—N1	1.279 (5)	C22—H21	0.960
C7—H4	0.930	C22—H22	0.960
C8—N1	1.476 (5)	C22—H23	0.960
C8—C9	1.483 (8)	Cu2—O1	1.939 (3)
C8—H5	0.970	Cu2—O3	1.947 (2)
C8—H6	0.970	Cu2—N2	1.957 (3)
C9—C10	1.493 (6)	Cu2—N1	1.989 (3)
C9—H8	0.970	Cu2—Tb1	3.4749 (16)
C9—H7	0.970	N3—O6	1.208 (4)
C10—N2	1.492 (5)	N3—O7	1.271 (4)
C10—H9	0.970	N3—O5	1.274 (4)
C10—H10	0.970	N4—O9	1.222 (4)
C11—N2	1.293 (5)	N4—O8	1.274 (4)
C11—C12	1.439 (5)	N4—O10	1.275 (4)
C11—H11	0.930	N5—O12	1.219 (4)
C12—C17	1.394 (5)	N5—O11	1.257 (4)
C12—C13	1.411 (5)	N5—O13	1.280 (5)
C13—C14	1.377 (6)	O1—Tb1	2.352 (2)
C13—H12	0.930	O2—Tb1	2.506 (3)
C14—C15	1.396 (6)	O3—Tb1	2.344 (3)
C14—H13	0.930	O4—Tb1	2.492 (2)
C15—C16	1.377 (5)	O5—Tb1	2.470 (3)
C15—H14	0.930	O7—Tb1	2.501 (3)
C16—O4	1.379 (4)	O8—Tb1	2.455 (3)
C16—C17	1.424 (4)	O10—Tb1	2.494 (3)
C17—O3	1.333 (4)	O11—Tb1	2.491 (3)
C18—O4	1.448 (4)	O13—Tb1	2.564 (3)
C18—H15	0.960

O1—C1—C2	117.8 (3)	O1—Cu2—Tb1	40.14 (7)
O1—C1—C6	122.7 (3)	O3—Cu2—Tb1	39.95 (7)
C2—C1—C6	119.5 (3)	N2—Cu2—Tb1	130.52 (9)
C3—C2—O2	124.7 (3)	N1—Cu2—Tb1	129.85 (10)
C3—C2—C1	120.6 (3)	C7—N1—C8	115.4 (3)
O2—C2—C1	114.7 (3)	C7—N1—Cu2	123.8 (3)
C2—C3—C4	119.8 (4)	C8—N1—Cu2	120.7 (3)
C2—C3—H1	120.1	C11—N2—C10	115.0 (3)
C4—C3—H1	120.1	C11—N2—Cu2	124.3 (2)
C5—C4—C3	120.7 (3)	C10—N2—Cu2	120.7 (2)
C5—C4—H2	119.7	O6—N3—O7	123.1 (4)
C3—C4—H2	119.7	O6—N3—O5	120.8 (4)
C4—C5—C6	120.5 (3)	O7—N3—O5	116.1 (3)
C4—C5—H3	119.7	O9—N4—O8	121.0 (4)
C6—C5—H3	119.7	O9—N4—O10	123.8 (4)
C5—C6—C1	118.9 (4)	O8—N4—O10	115.2 (3)
C5—C6—C7	118.6 (3)	O12—N5—O11	121.5 (4)
C1—C6—C7	122.3 (3)	O12—N5—O13	122.0 (4)
N1—C7—C6	128.9 (3)	O11—N5—O13	116.5 (3)
N1—C7—H4	115.6	C1—O1—Cu2	128.2 (2)
C6—C7—H4	115.6	C1—O1—Tb1	124.0 (2)
N1—C8—C9	113.1 (4)	Cu2—O1—Tb1	107.76 (10)
N1—C8—H5	109.0	C2—O2—C19	118.0 (3)
C9—C8—H5	109.0	C2—O2—Tb1	118.0 (2)
N1—C8—H6	109.0	C19—O2—Tb1	123.2 (2)
C9—C8—H6	109.0	C17—O3—Cu2	129.3 (2)
H5—C8—H6	107.8	C17—O3—Tb1	122.90 (19)
C8—C9—C10	112.3 (4)	Cu2—O3—Tb1	107.83 (10)
C8—C9—H8	109.1	C16—O4—C18	117.7 (3)
C10—C9—H8	109.1	C16—O4—Tb1	117.60 (18)
C8—C9—H7	109.1	C18—O4—Tb1	122.5 (2)
C10—C9—H7	109.1	N3—O5—Tb1	96.8 (2)
H8—C9—H7	107.9	N3—O7—Tb1	95.4 (2)
N2—C10—C9	111.7 (3)	N4—O8—Tb1	97.5 (2)
N2—C10—H9	109.3	N4—O10—Tb1	95.6 (2)
C9—C10—H9	109.3	N5—O11—Tb1	98.5 (2)
N2—C10—H10	109.3	N5—O13—Tb1	94.4 (2)
C9—C10—H10	109.3	O3—Tb1—O1	63.45 (9)
H9—C10—H10	107.9	O3—Tb1—O8	146.77 (9)
N2—C11—C12	128.6 (3)	O1—Tb1—O8	147.69 (9)
N2—C11—H11	115.7	O3—Tb1—O5	72.83 (9)
C12—C11—H11	115.7	O1—Tb1—O5	73.37 (10)
C17—C12—C13	119.4 (3)	O8—Tb1—O5	118.67 (9)
C17—C12—C11	122.6 (3)	O3—Tb1—O11	81.12 (10)
C13—C12—C11	117.9 (3)	O1—Tb1—O11	116.73 (9)
C14—C13—C12	120.2 (4)	O8—Tb1—O11	72.71 (10)
C14—C13—H12	119.9	O5—Tb1—O11	143.71 (10)
C12—C13—H12	119.9	O3—Tb1—O4	65.89 (8)
C13—C14—C15	121.0 (3)	O1—Tb1—O4	126.51 (9)
C13—C14—H13	119.5	O8—Tb1—O4	85.75 (9)
C15—C14—H13	119.5	O5—Tb1—O4	76.54 (9)
C16—C15—C14	119.5 (3)	O11—Tb1—O4	69.87 (9)
C16—C15—H14	120.2	O3—Tb1—O10	138.29 (9)
C14—C15—H14	120.2	O1—Tb1—O10	99.56 (9)
C15—C16—O4	124.8 (3)	O8—Tb1—O10	51.53 (9)
C15—C16—C17	120.5 (3)	O5—Tb1—O10	142.00 (10)
O4—C16—C17	114.6 (3)	O11—Tb1—O10	73.34 (10)
O3—C17—C12	122.4 (3)	O4—Tb1—O10	130.23 (8)
O3—C17—C16	118.3 (3)	O3—Tb1—O7	115.07 (9)
C12—C17—C16	119.3 (3)	O1—Tb1—O7	117.69 (9)
O4—C18—H15	109.5	O8—Tb1—O7	67.18 (9)
O4—C18—H16	109.5	O5—Tb1—O7	51.50 (9)
H15—C18—H16	109.5	O11—Tb1—O7	124.64 (9)
O4—C18—H17	109.5	O4—Tb1—O7	70.61 (10)
H15—C18—H17	109.5	O10—Tb1—O7	106.57 (10)
H16—C18—H17	109.5	O3—Tb1—O2	124.00 (8)
O2—C19—H18	109.5	O1—Tb1—O2	64.58 (8)
O2—C19—H19	109.5	O8—Tb1—O2	89.00 (9)
H18—C19—H19	109.5	O5—Tb1—O2	73.82 (9)
O2—C19—H20	109.5	O11—Tb1—O2	142.46 (9)
H18—C19—H20	109.5	O4—Tb1—O2	142.70 (9)
H19—C19—H20	109.5	O10—Tb1—O2	69.68 (9)
C21—C20—H24	109.5	O7—Tb1—O2	73.33 (9)
C21—C20—H25	109.5	O3—Tb1—O13	71.12 (10)
H24—C20—H25	109.5	O1—Tb1—O13	68.46 (10)
C21—C20—H26	109.5	O8—Tb1—O13	105.29 (10)
H24—C20—H26	109.5	O5—Tb1—O13	136.01 (10)
H25—C20—H26	109.5	O11—Tb1—O13	50.51 (10)
O14—C21—C20	121.7 (6)	O4—Tb1—O13	109.79 (10)
O14—C21—C22	121.8 (5)	O10—Tb1—O13	67.18 (10)
C20—C21—C22	116.4 (5)	O7—Tb1—O13	172.48 (9)
C21—C22—H21	109.5	O2—Tb1—O13	107.22 (10)
C21—C22—H22	109.5	O3—Tb1—Cu2	32.23 (5)
H21—C22—H22	109.5	O1—Tb1—Cu2	32.10 (6)
C21—C22—H23	109.5	O8—Tb1—Cu2	165.72 (6)
H21—C22—H23	109.5	O5—Tb1—Cu2	75.60 (7)
H22—C22—H23	109.5	O11—Tb1—Cu2	95.49 (8)
O1—Cu2—O3	78.92 (10)	O4—Tb1—Cu2	97.89 (6)
O1—Cu2—N2	170.42 (11)	O10—Tb1—Cu2	118.11 (7)
O3—Cu2—N2	91.51 (12)	O7—Tb1—Cu2	127.06 (6)
O1—Cu2—N1	91.40 (12)	O2—Tb1—Cu2	96.16 (6)
O3—Cu2—N1	169.69 (12)	O13—Tb1—Cu2	60.46 (7)
N2—Cu2—N1	98.17 (13)

Experimental details

Crystal data
Chemical formula	[CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃]·C₃H₆O
M_r	806.94
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	9.388 (5), 12.108 (6), 13.604 (6)
α, β, γ (°)	73.079 (16), 86.67 (2), 72.33 (2)
V (Å³)	1408.8 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.32
Crystal size (mm)	0.19 × 0.16 × 0.14

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.569, 0.659
No. of measured, independent and observed [I > 2σ(I)] reflections	12171, 6275, 5621
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.083, 1.11
No. of reflections	6275
No. of parameters	392
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.50

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu2—O1	1.939 (3)	O4—Tb1	2.492 (2)
Cu2—O3	1.947 (2)	O5—Tb1	2.470 (3)
Cu2—N2	1.957 (3)	O7—Tb1	2.501 (3)
Cu2—N1	1.989 (3)	O8—Tb1	2.455 (3)
O1—Tb1	2.352 (2)	O10—Tb1	2.494 (3)
O2—Tb1	2.506 (3)	O11—Tb1	2.491 (3)
O3—Tb1	2.344 (3)	O13—Tb1	2.564 (3)

Acknowledgements

The authors gratefully acknowledge financial support from the Education Department of Liaoning Province (2006 B 112) and Liaoning University.

References

Elmali, A. & Elerman, Y. (2003). Z. Naturforsch. Teil B, 58, 639–643. CAS Google Scholar
Elmali, A. & Elerman, Y. (2004). Z. Naturforsch. Teil B, 59, 535–540. CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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