(Acetone-2κO){μ-6,6′-dimeth­oxy-2,2′-[propane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato-κ81:2O6,O1,O1′,O6′:O1,N,N′,O1′}tris(nitrato-1κ2O,O′)copper(II)terbium(III)

Sun, W.-B.; Yan, P.-F.; Li, G.-M.; Hou, G.-F.

doi:10.1107/S1600536809022077

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m780-m781

doi:10.1107/S1600536809022077

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(Acetone-2κO){μ-6,6′-dimethoxy-2,2′-[propane-1,2-diylbis(nitrilomethylidyne)]diphenolato-κ⁸1:2O⁶,O¹,O^1′,O^6′:O¹,N,N′,O^1′}tris(nitrato-1κ²O,O′)copper(II)terbium(III)

Wen-Bin Sun,^a Peng-Fei Yan,^a Guang-Ming Li ^a ^* and Guang-Feng Hou ^b

^aKey Laboratory of Functional Inorganic Material Chemistry (HLJU), Ministry of Education, School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: gmli@hlju.edu.cn

(Received 19 May 2009; accepted 10 June 2009; online 17 June 2009)

In the title heteronuclear complex, [CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃(CH₃COCH₃)], the Cu^II ion is five-coordinated by two O and two N atoms from the 6,6′-dimethoxy-2,2′-[propane-1,2-diylbis(nitrilomethylidyne)]diphenolate ligand (L) and an O atom from the acetone molecule in a square-pyramidal geometry. The Tb^III ion is ten-coordinated by six O atoms from three chelating nitrate ligands and four O atoms from the L ligand. In L, the CH₂–CH–CH₃ fragment is disordered over two conformations, with refined occupancies of 0.725 (11) and 0.275 (11).

Related literature

For the copper–gadolinium and copper–praseodymium complexes of the N,N′-bis(3-methoxysalicylidene)propane-1,2-diamino ligand, see: Kara et al. (2000 ) and Sun et al. (2007 ), respectively.

Experimental

Crystal data

[CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃(C₃H₆O)]
M_r = 806.94
Monoclinic, P 2₁ /c
a = 9.8923 (9) Å
b = 18.8321 (18) Å
c = 15.5982 (15) Å
β = 95.085 (2)°
V = 2894.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.23 mm⁻¹
T = 291 K
0.20 × 0.19 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.563, T_max = 0.591 (expected range = 0.532–0.559)
15732 measured reflections
5696 independent reflections
4296 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.092
S = 1.02
5696 reflections
421 parameters
48 restraints
H-atom parameters constrained
Δρ_max = 1.12 e Å⁻³
Δρ_min = −0.53 e Å⁻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 I, global. DOI: 10.1107/S1600536809022077/cv2566sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022077/cv2566Isup2.hkl

checkCIF report

Comment top

The Schiff base Cu—Ln (Ln = rare earth) dinuclear complexes have attracted an attention due to their magnetic properties. In the title compound (Fig. 1), the octadentate Schiff base ligand links Cu and Tb atoms into a dinuclear complex through two phenolate O atoms, that is similar with the bonding reported for other copper-gadolinium and copper-praseodymium complexes of the ligand L = N,N'-bis(3- Methoxysalicylidene)propane-1,2-diamine (Kara et al., 2000; Sun et al., 2007). The Tb^III centre in the title complex is ten-coordinated by four oxygen atoms from ligand L and six oxygen atoms from three nitrato ligands. The Cu^II center is five-coordinate by two nitrogen atoms and two oxygen atoms from the ligand and one oxygen atom from acetone in a square-pyramidal geometry.

Related literature top

For the copper–gadolinium and copper–praseodymium complexes of the N,N'-bis(3-methoxysalicylidene)propane-1,2-diamino ligand, see: Kara et al. (2000) and Sun et al. (2007), respectively.

Experimental top

To a 1:1 MeOH/Me₂CO solution (20 ml) of the ligand L (0.086 g, 0.250 mmol) was slowly added an aqueous solution (8 ml) of [Cu(Ac)₂H₂O] (0.050 g, 0.25 mmol). After refluxing and stirring for 3 h, was slowly added a MeOH solution (10 ml) of Tb(NO₃)₃6H₂O (0.114 g, 0.25 mmol) at ambient temperature. After stirring for 5 h, red solid was collected by filtration and washed with MeOH, [CuTb(C₁₉H₂₀N₂O₄)(CH₃COCH₃)(NO₃)₃], yield 0.172 g (85%). Single crystals suitable for X-ray determination were obtained by slow diffusion of diethylether into a methanol solution of the powder sample over one week. Analysis calculated for C₂₂H₂₆CuN₅O₁₄Tb: C, 32.75; H, 3.25; N, 8.68; found: C, 32.81; H, 3.30; N, 8.80%.

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 of the title compound showing the atomic numbering and 30% probability displacement ellipsoids. Only major part of the disordered fragment is shown. H atoms omitted for clarity.

(Acetone-2κO){µ-6,6'-dimethoxy-2,2'-[propane-1,2- diylbis(nitrilomethylidyne)]diphenolato- κ⁸1:2O⁶,O¹,O^1',O^6': O¹,N,N',O^1'}tris(nitrato- 1κ²O,O')copper(II)terbium(III) top

Crystal data top

[CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃(C₃H₆O)]	F(000) = 1596
M_r = 806.94	D_x = 1.852 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3804 reflections
a = 9.8923 (9) Å	θ = 2.3–21.9°
b = 18.8321 (18) Å	µ = 3.23 mm⁻¹
c = 15.5982 (15) Å	T = 291 K
β = 95.085 (2)°	Block, red
V = 2894.4 (5) Å³	0.20 × 0.19 × 0.18 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5696 independent reflections
Radiation source: fine-focus sealed tube	4296 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 26.1°, θ_min = 1.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.563, T_max = 0.591	k = −23→16
15732 measured reflections	l = −19→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0427P)² + 0.3818P] where P = (F_o² + 2F_c²)/3
5696 reflections	(Δ/σ)_max = 0.003
421 parameters	Δρ_max = 1.12 e Å⁻³
48 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃(C₃H₆O)]	V = 2894.4 (5) Å³
M_r = 806.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8923 (9) Å	µ = 3.23 mm⁻¹
b = 18.8321 (18) Å	T = 291 K
c = 15.5982 (15) Å	0.20 × 0.19 × 0.18 mm
β = 95.085 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5696 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4296 reflections with I > 2σ(I)
T_min = 0.563, T_max = 0.591	R_int = 0.037
15732 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	48 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.02	Δρ_max = 1.12 e Å⁻³
5696 reflections	Δρ_min = −0.53 e Å⁻³
421 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	Occ. (<1)
Tb1	0.28678 (3)	0.074476 (12)	0.751003 (15)	0.04448 (10)
Cu1	0.20813 (8)	0.24090 (4)	0.67475 (5)	0.0633 (2)
N1	0.2390 (6)	0.3365 (3)	0.7107 (4)	0.0942 (19)
N2	0.1210 (6)	0.2826 (3)	0.5712 (4)	0.0845 (17)
N3	0.5440 (5)	0.0470 (3)	0.6857 (3)	0.0578 (12)
N4	0.0279 (7)	0.0890 (3)	0.8196 (4)	0.0816 (17)
N5	0.2699 (6)	−0.0635 (2)	0.8377 (3)	0.0685 (14)
O1	0.4538 (4)	0.12109 (18)	0.8774 (2)	0.0554 (9)
O2	0.3134 (4)	0.19791 (18)	0.7687 (2)	0.0580 (10)
O3	0.1984 (4)	0.14580 (18)	0.6349 (2)	0.0586 (10)
O4	0.2368 (4)	0.01506 (19)	0.6000 (2)	0.0560 (9)
O5	0.4863 (4)	0.1047 (2)	0.6734 (3)	0.0729 (12)
O6	0.4893 (4)	0.0038 (2)	0.7354 (3)	0.0671 (11)
O7	0.6477 (5)	0.0309 (3)	0.6551 (4)	0.1129 (18)
O8	0.1350 (6)	0.1106 (3)	0.8570 (3)	0.1117 (19)
O9	0.0401 (5)	0.0624 (3)	0.7478 (3)	0.0940 (15)
O10	−0.0824 (6)	0.0945 (3)	0.8491 (4)	0.130 (2)
O11	0.3161 (5)	−0.0093 (2)	0.8754 (3)	0.0913 (15)
O12	0.2238 (5)	−0.0545 (2)	0.7621 (3)	0.0768 (13)
O13	0.2657 (6)	−0.1202 (2)	0.8738 (3)	0.1142 (19)
C19	0.5588 (7)	0.0802 (3)	0.9243 (4)	0.080 (2)
H1A	0.6425	0.1062	0.9276	0.120*
H1B	0.5700	0.0359	0.8953	0.120*
H1C	0.5338	0.0711	0.9814	0.120*
C2	0.4457 (5)	0.1926 (3)	0.8984 (3)	0.0519 (13)
C3	0.5042 (6)	0.2224 (3)	0.9726 (4)	0.0738 (18)
H1	0.5525	0.1948	1.0143	0.089*
C4	0.4894 (7)	0.2961 (4)	0.9841 (5)	0.088 (2)
H2	0.5261	0.3173	1.0347	0.106*
C5	0.4232 (6)	0.3357 (3)	0.9229 (5)	0.084 (2)
H3	0.4171	0.3844	0.9319	0.101*
C6	0.3635 (6)	0.3078 (3)	0.8468 (4)	0.0629 (16)
C1	0.3703 (5)	0.2330 (3)	0.8362 (4)	0.0512 (13)
C7	0.3023 (6)	0.3546 (3)	0.7814 (6)	0.088 (2)
H4	0.3102	0.4030	0.7922	0.106*
C8	0.1969 (14)	0.3843 (6)	0.6358 (7)	0.098 (4)	0.688 (12)
H8	0.1681	0.4294	0.6598	0.118*	0.688 (12)
C9	0.0831 (18)	0.3580 (4)	0.5792 (11)	0.159 (10)	0.688 (12)
H9A	0.0767	0.3819	0.5239	0.191*	0.688 (12)
H9B	−0.0020	0.3632	0.6050	0.191*	0.688 (12)
C10	0.2949 (16)	0.4011 (8)	0.5767 (10)	0.165 (7)	0.688 (12)
H10A	0.3065	0.3610	0.5401	0.247*	0.688 (12)
H10B	0.3799	0.4125	0.6081	0.247*	0.688 (12)
H10C	0.2638	0.4411	0.5422	0.247*	0.688 (12)
C8'	0.128 (2)	0.3834 (11)	0.6722 (16)	0.086 (6)	0.312 (12)
H8'	0.0445	0.3815	0.7011	0.104*	0.312 (12)
C9'	0.114 (4)	0.3599 (6)	0.5828 (18)	0.093 (7)	0.312 (12)
H9'1	0.1845	0.3819	0.5527	0.112*	0.312 (12)
H9'2	0.0272	0.3766	0.5563	0.112*	0.312 (12)
C10'	0.160 (3)	0.4509 (17)	0.642 (2)	0.145 (13)	0.312 (12)
H10D	0.1263	0.4866	0.6781	0.217*	0.312 (12)
H10E	0.1187	0.4568	0.5840	0.217*	0.312 (12)
H10F	0.2566	0.4556	0.6418	0.217*	0.312 (12)
C11	0.0870 (7)	0.2485 (5)	0.5039 (5)	0.090 (2)
H5	0.0502	0.2748	0.4570	0.108*
C12	0.0984 (6)	0.1733 (4)	0.4908 (4)	0.0711 (18)
C13	0.0550 (7)	0.1448 (5)	0.4103 (4)	0.088 (2)
H6	0.0158	0.1747	0.3676	0.105*
C14	0.0686 (7)	0.0750 (5)	0.3928 (4)	0.093 (3)
H7	0.0362	0.0576	0.3391	0.112*
C15	0.1290 (6)	0.0298 (4)	0.4528 (3)	0.0719 (18)
H15	0.1404	−0.0179	0.4397	0.086*
C16	0.1730 (5)	0.0556 (3)	0.5332 (3)	0.0553 (14)
C17	0.1551 (5)	0.1262 (3)	0.5541 (3)	0.0555 (14)
C18	0.2845 (7)	−0.0536 (3)	0.5759 (4)	0.0720 (17)
H18A	0.2083	−0.0841	0.5608	0.108*
H18B	0.3397	−0.0738	0.6234	0.108*
H18C	0.3372	−0.0487	0.5275	0.108*
O14	−0.0246 (4)	0.2439 (2)	0.7447 (3)	0.0792 (13)
C20	−0.2527 (8)	0.2460 (5)	0.7791 (5)	0.113 (3)
H20A	−0.2683	0.2062	0.8154	0.169*
H20B	−0.3344	0.2568	0.7437	0.169*
H20C	−0.2263	0.2864	0.8143	0.169*
C21	−0.1421 (7)	0.2283 (3)	0.7233 (4)	0.0689 (17)
C22	−0.1803 (7)	0.1933 (4)	0.6404 (4)	0.090 (2)
H22A	−0.1000	0.1768	0.6162	0.135*
H22B	−0.2272	0.2265	0.6017	0.135*
H22C	−0.2385	0.1537	0.6492	0.135*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Tb1	0.05575 (17)	0.03633 (15)	0.04035 (16)	0.00036 (12)	−0.00140 (11)	0.00182 (11)
Cu1	0.0784 (5)	0.0434 (4)	0.0669 (5)	0.0103 (3)	0.0002 (4)	0.0158 (3)
N1	0.104 (5)	0.044 (3)	0.128 (5)	0.001 (3)	−0.023 (4)	0.018 (3)
N2	0.104 (4)	0.077 (4)	0.073 (4)	0.034 (3)	0.011 (3)	0.037 (3)
N3	0.058 (3)	0.047 (3)	0.071 (3)	0.001 (2)	0.021 (3)	−0.004 (3)
N4	0.088 (5)	0.073 (4)	0.088 (5)	0.007 (3)	0.032 (4)	0.006 (3)
N5	0.091 (4)	0.043 (3)	0.068 (4)	−0.016 (3)	−0.014 (3)	0.016 (3)
O1	0.066 (2)	0.046 (2)	0.051 (2)	0.0027 (18)	−0.0140 (18)	−0.0006 (17)
O2	0.073 (3)	0.036 (2)	0.062 (2)	0.0043 (17)	−0.012 (2)	−0.0011 (17)
O3	0.080 (3)	0.053 (2)	0.041 (2)	0.0143 (19)	−0.0046 (19)	0.0065 (17)
O4	0.069 (2)	0.055 (2)	0.044 (2)	0.0031 (19)	0.0036 (18)	−0.0063 (18)
O5	0.077 (3)	0.056 (3)	0.089 (3)	0.009 (2)	0.023 (2)	0.021 (2)
O6	0.069 (3)	0.047 (2)	0.086 (3)	0.005 (2)	0.011 (2)	0.010 (2)
O7	0.098 (4)	0.084 (3)	0.166 (5)	0.015 (3)	0.063 (3)	0.012 (3)
O8	0.089 (4)	0.157 (5)	0.093 (4)	−0.015 (4)	0.031 (3)	−0.047 (4)
O9	0.072 (3)	0.121 (4)	0.089 (4)	−0.004 (3)	0.006 (3)	−0.021 (3)
O10	0.089 (4)	0.160 (6)	0.150 (6)	−0.001 (4)	0.060 (4)	−0.004 (4)
O11	0.151 (4)	0.059 (3)	0.058 (3)	−0.038 (3)	−0.016 (3)	0.006 (2)
O12	0.099 (3)	0.066 (3)	0.061 (3)	−0.022 (2)	−0.019 (2)	0.012 (2)
O13	0.170 (5)	0.058 (3)	0.106 (4)	−0.032 (3)	−0.037 (4)	0.035 (3)
C19	0.093 (5)	0.061 (4)	0.079 (5)	0.007 (3)	−0.034 (4)	0.002 (3)
C2	0.055 (3)	0.042 (3)	0.058 (3)	−0.006 (2)	0.000 (3)	−0.012 (3)
C3	0.071 (4)	0.073 (4)	0.075 (4)	−0.005 (3)	−0.009 (3)	−0.018 (4)
C4	0.078 (5)	0.079 (5)	0.108 (6)	−0.018 (4)	0.001 (4)	−0.051 (4)
C5	0.060 (4)	0.052 (4)	0.139 (7)	0.000 (3)	0.003 (4)	−0.032 (4)
C6	0.050 (3)	0.049 (4)	0.090 (5)	−0.008 (3)	0.008 (3)	−0.018 (3)
C1	0.042 (3)	0.047 (3)	0.063 (4)	−0.001 (2)	0.002 (3)	−0.007 (3)
C7	0.067 (4)	0.034 (3)	0.162 (8)	0.000 (3)	−0.002 (5)	0.005 (4)
C8	0.125 (8)	0.042 (5)	0.129 (8)	0.015 (5)	0.024 (7)	0.035 (5)
C9	0.25 (3)	0.102 (12)	0.117 (12)	0.018 (12)	−0.056 (14)	0.049 (10)
C10	0.170 (11)	0.142 (10)	0.186 (11)	−0.007 (8)	0.030 (8)	−0.002 (8)
C8'	0.090 (10)	0.072 (9)	0.098 (9)	0.012 (8)	0.017 (8)	0.016 (7)
C9'	0.103 (11)	0.085 (9)	0.092 (9)	0.032 (9)	0.010 (8)	0.009 (9)
C10'	0.150 (16)	0.142 (16)	0.145 (16)	0.002 (10)	0.025 (10)	0.001 (10)
C11	0.082 (5)	0.121 (7)	0.068 (5)	0.039 (5)	0.014 (4)	0.043 (5)
C12	0.055 (3)	0.106 (6)	0.052 (4)	0.012 (4)	0.007 (3)	0.029 (4)
C13	0.070 (4)	0.144 (8)	0.047 (4)	0.008 (5)	−0.006 (3)	0.025 (5)
C14	0.076 (5)	0.165 (9)	0.037 (4)	−0.015 (5)	−0.001 (3)	0.006 (5)
C15	0.059 (4)	0.115 (6)	0.042 (4)	−0.013 (4)	0.005 (3)	−0.009 (4)
C16	0.048 (3)	0.071 (4)	0.047 (3)	−0.001 (3)	0.006 (3)	−0.003 (3)
C17	0.046 (3)	0.087 (5)	0.033 (3)	0.006 (3)	0.004 (2)	0.008 (3)
C18	0.084 (4)	0.067 (4)	0.065 (4)	0.010 (3)	0.009 (3)	−0.016 (3)
O14	0.068 (3)	0.082 (3)	0.088 (3)	−0.014 (2)	0.010 (2)	−0.017 (2)
C20	0.085 (5)	0.128 (7)	0.131 (7)	−0.005 (5)	0.046 (5)	−0.018 (6)
C21	0.063 (4)	0.058 (4)	0.086 (5)	−0.002 (3)	0.009 (4)	0.006 (3)
C22	0.074 (4)	0.098 (6)	0.096 (5)	−0.015 (4)	−0.005 (4)	−0.014 (4)

Geometric parameters (Å, º) top

Tb1—O2	2.353 (3)	C4—H2	0.9300
Tb1—O3	2.360 (3)	C5—C6	1.382 (8)
Tb1—O8	2.427 (5)	C5—H3	0.9300
Tb1—O6	2.436 (4)	C6—C1	1.419 (7)
Tb1—O9	2.446 (5)	C6—C7	1.441 (9)
Tb1—O5	2.472 (4)	C7—H4	0.9300
Tb1—O11	2.498 (4)	C8—C10	1.431 (7)
Tb1—O12	2.517 (4)	C8—C9	1.455 (7)
Tb1—O1	2.610 (3)	C8—H8	0.9800
Tb1—O4	2.616 (3)	C9—H9A	0.9700
Tb1—N3	2.871 (5)	C9—H9B	0.9700
Tb1—N4	2.875 (6)	C10—H10A	0.9600
Cu1—O3	1.895 (4)	C10—H10B	0.9600
Cu1—O2	1.901 (3)	C10—H10C	0.9600
Cu1—N1	1.903 (6)	C8'—C10'	1.40 (4)
Cu1—N2	1.929 (5)	C8'—C9'	1.457 (7)
N1—C7	1.265 (9)	C8'—H8'	0.9800
N1—C8'	1.490 (7)	C9'—H9'1	0.9700
N1—C8	1.504 (6)	C9'—H9'2	0.9700
N2—C11	1.251 (9)	C10'—H10D	0.9600
N2—C9'	1.469 (7)	C10'—H10E	0.9600
N2—C9	1.476 (7)	C10'—H10F	0.9600
N3—O7	1.208 (6)	C11—C12	1.438 (10)
N3—O5	1.234 (6)	C11—H5	0.9300
N3—O6	1.277 (5)	C12—C13	1.399 (9)
N4—O10	1.225 (7)	C12—C17	1.405 (7)
N4—O8	1.233 (7)	C13—C14	1.350 (9)
N4—O9	1.242 (7)	C13—H6	0.9300
N5—O13	1.211 (6)	C14—C15	1.364 (9)
N5—O12	1.237 (6)	C14—H7	0.9300
N5—O11	1.244 (6)	C15—C16	1.379 (7)
O1—C2	1.390 (6)	C15—H15	0.9300
O1—C19	1.440 (6)	C16—C17	1.385 (8)
O2—C1	1.326 (6)	C18—H18A	0.9600
O3—C17	1.346 (6)	C18—H18B	0.9600
O4—C16	1.396 (6)	C18—H18C	0.9600
O4—C18	1.437 (6)	O14—C21	1.217 (7)
C19—H1A	0.9600	C20—C21	1.495 (9)
C19—H1B	0.9600	C20—H20A	0.9600
C19—H1C	0.9600	C20—H20B	0.9600
C2—C3	1.368 (7)	C20—H20C	0.9600
C2—C1	1.397 (7)	C21—C22	1.471 (8)
C3—C4	1.408 (8)	C22—H22A	0.9600
C3—H1	0.9300	C22—H22B	0.9600
C4—C5	1.337 (9)	C22—H22C	0.9600

O2—Tb1—O3	63.73 (12)	C17—O3—Cu1	124.6 (3)
O2—Tb1—O8	73.33 (17)	C17—O3—Tb1	128.9 (3)
O3—Tb1—O8	98.85 (18)	Cu1—O3—Tb1	106.35 (15)
O2—Tb1—O6	117.86 (13)	C16—O4—C18	115.7 (4)
O3—Tb1—O6	119.11 (13)	C16—O4—Tb1	118.3 (3)
O8—Tb1—O6	141.76 (18)	C18—O4—Tb1	125.4 (3)
O2—Tb1—O9	101.25 (15)	N3—O5—Tb1	95.7 (3)
O3—Tb1—O9	74.70 (15)	N3—O6—Tb1	96.2 (3)
O8—Tb1—O9	50.48 (17)	N4—O8—Tb1	98.2 (4)
O6—Tb1—O9	140.80 (15)	N4—O9—Tb1	97.0 (4)
O2—Tb1—O5	75.17 (13)	N5—O11—Tb1	97.9 (3)
O3—Tb1—O5	75.56 (13)	N5—O12—Tb1	97.2 (3)
O8—Tb1—O5	146.97 (18)	O1—C19—H1A	109.5
O6—Tb1—O5	51.47 (13)	O1—C19—H1B	109.5
O9—Tb1—O5	148.17 (16)	H1A—C19—H1B	109.5
O2—Tb1—O11	121.96 (13)	O1—C19—H1C	109.5
O3—Tb1—O11	164.89 (15)	H1A—C19—H1C	109.5
O8—Tb1—O11	71.6 (2)	H1B—C19—H1C	109.5
O6—Tb1—O11	72.08 (15)	C3—C2—O1	124.6 (5)
O9—Tb1—O11	90.24 (17)	C3—C2—C1	121.6 (5)
O5—Tb1—O11	118.88 (16)	O1—C2—C1	113.8 (4)
O2—Tb1—O12	166.19 (14)	C2—C3—C4	118.1 (6)
O3—Tb1—O12	121.65 (13)	C2—C3—H1	120.9
O8—Tb1—O12	92.96 (18)	C4—C3—H1	120.9
O6—Tb1—O12	71.95 (14)	C5—C4—C3	120.6 (6)
O9—Tb1—O12	70.09 (16)	C5—C4—H2	119.7
O5—Tb1—O12	117.97 (15)	C3—C4—H2	119.7
O11—Tb1—O12	49.42 (13)	C4—C5—C6	123.0 (6)
O2—Tb1—O1	61.47 (11)	C4—C5—H3	118.5
O3—Tb1—O1	123.72 (12)	C6—C5—H3	118.5
O8—Tb1—O1	77.27 (16)	C5—C6—C1	117.2 (6)
O6—Tb1—O1	77.77 (12)	C5—C6—C7	119.8 (6)
O9—Tb1—O1	127.60 (15)	C1—C6—C7	123.0 (6)
O5—Tb1—O1	79.22 (13)	O2—C1—C2	116.3 (5)
O11—Tb1—O1	66.65 (12)	O2—C1—C6	124.5 (5)
O12—Tb1—O1	114.63 (12)	C2—C1—C6	119.2 (5)
O2—Tb1—O4	122.57 (12)	N1—C7—C6	126.7 (6)
O3—Tb1—O4	61.61 (12)	N1—C7—H4	116.6
O8—Tb1—O4	130.88 (16)	C6—C7—H4	116.6
O6—Tb1—O4	76.55 (13)	C10—C8—C9	102.5 (14)
O9—Tb1—O4	80.41 (15)	C10—C8—N1	118.4 (11)
O5—Tb1—O4	75.68 (13)	C9—C8—N1	114.4 (10)
O11—Tb1—O4	115.40 (13)	C10—C8—H8	106.9
O12—Tb1—O4	67.72 (12)	C9—C8—H8	106.9
O1—Tb1—O4	151.75 (11)	N1—C8—H8	106.9
O2—Tb1—N3	97.24 (13)	C8—C9—N2	101.0 (10)
O3—Tb1—N3	96.33 (14)	C8—C9—H9A	111.6
O8—Tb1—N3	156.01 (17)	N2—C9—H9A	111.6
O6—Tb1—N3	26.24 (12)	C8—C9—H9B	111.6
O9—Tb1—N3	152.87 (16)	N2—C9—H9B	111.6
O5—Tb1—N3	25.33 (13)	H9A—C9—H9B	109.4
O11—Tb1—N3	96.66 (16)	C10'—C8'—C9'	87.5 (18)
O12—Tb1—N3	94.76 (15)	C10'—C8'—N1	120 (2)
O1—Tb1—N3	78.85 (13)	C9'—C8'—N1	102.3 (19)
O4—Tb1—N3	72.91 (12)	C10'—C8'—H8'	114.4
O2—Tb1—N4	87.52 (15)	C9'—C8'—H8'	114.4
O3—Tb1—N4	87.12 (16)	N1—C8'—H8'	114.4
O8—Tb1—N4	25.11 (16)	C8'—C9'—N2	114.7 (19)
O6—Tb1—N4	148.99 (15)	C8'—C9'—H9'1	108.6
O9—Tb1—N4	25.39 (16)	N2—C9'—H9'1	108.6
O5—Tb1—N4	159.54 (15)	C8'—C9'—H9'2	108.6
O11—Tb1—N4	79.46 (18)	N2—C9'—H9'2	108.6
O12—Tb1—N4	80.33 (16)	H9'1—C9'—H9'2	107.6
O1—Tb1—N4	102.25 (17)	C8'—C10'—H10D	109.5
O4—Tb1—N4	105.80 (17)	C8'—C10'—H10E	109.5
N3—Tb1—N4	175.01 (15)	H10D—C10'—H10E	109.5
O3—Cu1—O2	81.88 (15)	C8'—C10'—H10F	109.5
O3—Cu1—N1	173.3 (2)	H10D—C10'—H10F	109.5
O2—Cu1—N1	96.5 (2)	H10E—C10'—H10F	109.5
O3—Cu1—N2	96.0 (2)	N2—C11—C12	127.3 (6)
O2—Cu1—N2	172.7 (2)	N2—C11—H5	116.4
N1—Cu1—N2	84.8 (3)	C12—C11—H5	116.4
O3—Cu1—Tb1	41.50 (10)	C13—C12—C17	117.5 (7)
O2—Cu1—Tb1	41.33 (11)	C13—C12—C11	118.9 (6)
N1—Cu1—Tb1	137.72 (17)	C17—C12—C11	123.6 (6)
N2—Cu1—Tb1	137.4 (2)	C14—C13—C12	121.8 (7)
C7—N1—C8'	118.8 (11)	C14—C13—H6	119.1
C7—N1—C8	126.7 (7)	C12—C13—H6	119.1
C8'—N1—C8	35.8 (9)	C13—C14—C15	120.9 (7)
C7—N1—Cu1	124.4 (5)	C13—C14—H7	119.5
C8'—N1—Cu1	110.4 (10)	C15—C14—H7	119.5
C8—N1—Cu1	108.2 (6)	C14—C15—C16	119.2 (7)
C11—N2—C9'	126.8 (13)	C14—C15—H15	120.4
C11—N2—C9	120.9 (8)	C16—C15—H15	120.4
C9'—N2—C9	12 (2)	C15—C16—C17	121.1 (6)
C11—N2—Cu1	124.1 (5)	C15—C16—O4	124.8 (6)
C9'—N2—Cu1	108.9 (12)	C17—C16—O4	114.1 (5)
C9—N2—Cu1	114.8 (7)	O3—C17—C16	116.5 (5)
O7—N3—O5	123.8 (5)	O3—C17—C12	124.0 (6)
O7—N3—O6	120.0 (5)	C16—C17—C12	119.4 (5)
O5—N3—O6	116.2 (4)	O4—C18—H18A	109.5
O7—N3—Tb1	174.9 (4)	O4—C18—H18B	109.5
O5—N3—Tb1	59.0 (3)	H18A—C18—H18B	109.5
O6—N3—Tb1	57.5 (3)	O4—C18—H18C	109.5
O10—N4—O8	123.5 (7)	H18A—C18—H18C	109.5
O10—N4—O9	122.3 (7)	H18B—C18—H18C	109.5
O8—N4—O9	114.2 (6)	C21—C20—H20A	109.5
O10—N4—Tb1	179.4 (5)	C21—C20—H20B	109.5
O8—N4—Tb1	56.7 (3)	H20A—C20—H20B	109.5
O9—N4—Tb1	57.6 (3)	C21—C20—H20C	109.5
O13—N5—O12	122.6 (5)	H20A—C20—H20C	109.5
O13—N5—O11	122.0 (5)	H20B—C20—H20C	109.5
O12—N5—O11	115.3 (5)	O14—C21—C22	120.9 (6)
O13—N5—Tb1	178.7 (5)	O14—C21—C20	121.1 (7)
O12—N5—Tb1	58.2 (3)	C22—C21—C20	117.9 (6)
O11—N5—Tb1	57.3 (3)	C21—C22—H22A	109.5
C2—O1—C19	116.9 (4)	C21—C22—H22B	109.5
C2—O1—Tb1	117.3 (3)	H22A—C22—H22B	109.5
C19—O1—Tb1	125.7 (3)	C21—C22—H22C	109.5
C1—O2—Cu1	124.4 (3)	H22A—C22—H22C	109.5
C1—O2—Tb1	128.4 (3)	H22B—C22—H22C	109.5
Cu1—O2—Tb1	106.42 (16)

Experimental details

Crystal data
Chemical formula	[CuTb(C₁₉H₂₀N₂O₄)(NO₃)₃(C₃H₆O)]
M_r	806.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	9.8923 (9), 18.8321 (18), 15.5982 (15)
β (°)	95.085 (2)
V (Å³)	2894.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.23
Crystal size (mm)	0.20 × 0.19 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.563, 0.591
No. of measured, independent and observed [I > 2σ(I)] reflections	15732, 5696, 4296
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.092, 1.02
No. of reflections	5696
No. of parameters	421
No. of restraints	48
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.12, −0.53

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

Acknowledgements

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20572018 and 20672032), Heilongjiang Province (grant Nos. 11531284, 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University (grant Nos. 09k137, 09k117 and 09k118).

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kara, H., Elerman, Y. & Prout, K. (2000). Z. Naturforsch. Teil B, 55, 1131–1136. CAS 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
Sun, W.-B., Gao, T., Yan, P.-F., Li, G.-M. & Hou, G.-F. (2007). Acta Cryst. E63, m2192. Web of Science CSD CrossRef IUCr Journals Google Scholar

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