{μ-6,6′-Dimeth­oxy-2,2′-[propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato}trinitratocopper(II)europium(III)

Xing, J.-C.; Wang, J.-H.; Yan, P.-F.; Li, G.-M.

doi:10.1107/S1600536808026329

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1206

doi:10.1107/S1600536808026329

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{μ-6,6′-Dimethoxy-2,2′-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato}trinitratocopper(II)europium(III)

Jing-Chun Xing,^a,^b Jing-Hua Wang,^b Peng-Fei Yan ^b and Guang-Ming Li ^b ^*

^aSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bDepartment of Anesthesiology of the Second Affiliated Hospital, Harbin Medical University, Harbin 150086, People's Republic of China
^*Correspondence e-mail: gmli@hlju.edu.cn

(Received 29 July 2008; accepted 14 August 2008; online 30 August 2008)

In the title complex, [CuEu(C₁₉H₂₀N₂O₄)(NO₃)₃], the Cu^II ion is four-coordinated in a square-planar geometry by two O atoms and two N atoms of the deprotonated Schiff base. The Eu^III atom is ten-coordinate, chelated by three nitrate groups and linked to the four O atoms of the deprotonated Schiff base.

Related literature

For copper–lanthanide complexes of the same Schiff base, see: Elmali & Elerman (2003 ); Elmali & Elerman (2004 ).

Experimental

Crystal data

[CuEu(C₁₉H₂₀N₂O₄)(NO₃)₃]
M_r = 741.90
Monoclinic, P 2₁ /n
a = 11.638 (2) Å
b = 14.680 (3) Å
c = 14.853 (3) Å
β = 101.52 (3)°
V = 2486.5 (9) Å³
Z = 4
Mo Kα radiation
μ = 3.43 mm⁻¹
T = 291 (2) K
0.21 × 0.20 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.527, T_max = 0.568 (expected range = 0.484–0.521)
23524 measured reflections
5660 independent reflections
5072 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.058
S = 1.06
5660 reflections
354 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.45 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/S1600536808026329/fj2142sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026329/fj2142Isup2.hkl

checkCIF report

Comment top

As shown in Fig. 1, the hexadentate Schiff base ligand links Cu and Eu atoms into a dinuclear complex through two phenolate O atoms, which is similar with the bonding reported for another copper-lanthanide complex of the same ligand (Elmali & Elerman, 2003, 2004). The Eu^III centre in (I) is ten-coordinated by four oxygen atoms from the ligand and six oxygen atoms from three nitrate ions. The Cu^II center is four-coordinate by two nitrogen atoms and two oxygen atoms from the ligand.

Related literature top

For copper–lanthanide complexes of the same Schiff base, see: Elmali & Elerman (2003); Elmali & Elerman (2004).

Experimental top

The title complex was obtained by the treatment of copper(II) acetate monohydrate (0.0499 g, 0.25 mmol) with the Schiff base (0.0855 g, 0.25 mmol) in methanol (25 ml)at room temperature. Then the mixture was refluxed for 3 h after the addition of europium (III) nitrate hexahydrate (0.1117 g, 0.25 mmol). The reaction mixture was cooled and filtered; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Single crystals were obtained after several days. Analysis calculated for C₁₉H₂₀CuN₅O₁₃Eu: C, 30.78; H, 2.76; Cu, 8.50; N, 9.38; Eu, 20.58; found: C, 30.73; H, 2.70; Cu, 8.56; N, 9.44; Eu, 20.61%.

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 (I), showing 40% probability displacement ellipsoids.

{µ-6,6'-Dimethoxy-2,2'-[propane-1,3- diylbis(nitrilomethylidyne)]diphenolato} trinitratocopper(II)europium(III) top

Crystal data top

[CuEu(C₁₉H₂₀N₂O₄)(NO₃)₃]	F(000) = 1460
M_r = 741.90	D_x = 1.982 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 17062 reflections
a = 11.638 (2) Å	θ = 3.0–27.5°
b = 14.680 (3) Å	µ = 3.43 mm⁻¹
c = 14.853 (3) Å	T = 291 K
β = 101.52 (3)°	Block, red
V = 2486.5 (9) Å³	0.21 × 0.20 × 0.19 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5660 independent reflections
Radiation source: fine-focus sealed tube	5072 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −15→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
T_min = 0.527, T_max = 0.568	l = −19→19
23524 measured reflections

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0213P)² + 2.281P] where P = (F_o² + 2F_c²)/3
5660 reflections	(Δ/σ)_max = 0.002
354 parameters	Δρ_max = 0.72 e Å⁻³
6 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[CuEu(C₁₉H₂₀N₂O₄)(NO₃)₃]	V = 2486.5 (9) Å³
M_r = 741.90	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.638 (2) Å	µ = 3.43 mm⁻¹
b = 14.680 (3) Å	T = 291 K
c = 14.853 (3) Å	0.21 × 0.20 × 0.19 mm
β = 101.52 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5660 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5072 reflections with I > 2σ(I)
T_min = 0.527, T_max = 0.568	R_int = 0.031
23524 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	6 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.06	Δρ_max = 0.72 e Å⁻³
5660 reflections	Δρ_min = −0.45 e Å⁻³
354 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	0.9061 (2)	0.36789 (18)	−0.06244 (19)	0.0317 (6)
C2	0.7932 (3)	0.3919 (2)	−0.10789 (19)	0.0345 (6)
C3	0.7755 (3)	0.4599 (2)	−0.1732 (2)	0.0449 (7)
H1	0.6999	0.4743	−0.2038	0.054*
C4	0.8712 (3)	0.5068 (2)	−0.1931 (2)	0.0523 (9)
H2	0.8594	0.5536	−0.2361	0.063*
C5	0.9823 (3)	0.4844 (2)	−0.1499 (2)	0.0463 (8)
H3	1.0456	0.5162	−0.1639	0.056*
C6	1.0024 (3)	0.4136 (2)	−0.0841 (2)	0.0365 (6)
C7	1.1218 (3)	0.3936 (2)	−0.0403 (2)	0.0397 (7)
H4	1.1783	0.4344	−0.0518	0.048*
C8	1.2885 (3)	0.3275 (2)	0.0496 (3)	0.0536 (9)
H5	1.3080	0.3813	0.0876	0.064*
H6	1.3290	0.3320	−0.0013	0.064*
C9	1.3326 (3)	0.2449 (2)	0.1056 (3)	0.0511 (9)
H7	1.3038	0.2462	0.1625	0.061*
H8	1.4176	0.2469	0.1211	0.061*
C10	1.2950 (3)	0.1573 (2)	0.0561 (3)	0.0488 (8)
H9	1.2975	0.1638	−0.0085	0.059*
H10	1.3483	0.1088	0.0815	0.059*
C11	1.1568 (2)	0.05275 (19)	0.09083 (19)	0.0336 (6)
H11	1.2194	0.0126	0.0954	0.040*
C12	1.0502 (2)	0.01617 (18)	0.11234 (18)	0.0304 (6)
C13	1.0533 (3)	−0.0754 (2)	0.1430 (2)	0.0380 (7)
H12	1.1202	−0.1105	0.1442	0.046*
C14	0.9582 (3)	−0.1123 (2)	0.1709 (2)	0.0458 (8)
H13	0.9602	−0.1727	0.1899	0.055*
C15	0.8589 (3)	−0.0602 (2)	0.1710 (2)	0.0413 (7)
H14	0.7953	−0.0853	0.1914	0.050*
C16	0.8541 (2)	0.02870 (19)	0.14095 (19)	0.0321 (6)
C17	0.9492 (2)	0.06820 (17)	0.10940 (17)	0.0282 (5)
C18	0.6700 (3)	0.0552 (3)	0.1857 (3)	0.0560 (9)
H15	0.6339	0.0016	0.1553	0.084*
H16	0.6119	0.1019	0.1839	0.084*
H17	0.7039	0.0408	0.2484	0.084*
C19	0.5899 (3)	0.3491 (3)	−0.1377 (3)	0.0647 (11)
H18	0.5650	0.4115	−0.1394	0.097*
H19	0.5363	0.3122	−0.1121	0.097*
H20	0.5913	0.3287	−0.1988	0.097*
Cu1	1.05535 (3)	0.22819 (2)	0.03974 (2)	0.03036 (8)
Eu1	0.762074 (11)	0.247433 (8)	0.068399 (9)	0.02785 (5)
N1	1.1594 (2)	0.32671 (17)	0.01249 (18)	0.0382 (6)
N2	1.1746 (2)	0.13432 (16)	0.06616 (17)	0.0341 (5)
N3	0.6075 (3)	0.12249 (19)	−0.0485 (2)	0.0504 (7)
N4	0.8226 (5)	0.2655 (3)	0.2660 (2)	0.0872 (15)
N5	0.6480 (2)	0.42062 (17)	0.09471 (18)	0.0433 (6)
O1	0.91672 (16)	0.30177 (13)	0.00059 (14)	0.0353 (4)
O2	0.70508 (18)	0.34136 (15)	−0.08175 (14)	0.0399 (5)
O3	0.93757 (16)	0.15332 (12)	0.07838 (13)	0.0324 (4)
O4	0.76063 (18)	0.08689 (14)	0.13955 (15)	0.0390 (5)
O5	0.7096 (2)	0.13933 (16)	−0.06160 (16)	0.0478 (5)
O6	0.5492 (3)	0.0630 (2)	−0.0900 (3)	0.1037 (13)
O7	0.57208 (18)	0.17165 (15)	0.01090 (16)	0.0445 (5)
O8	0.7188 (3)	0.25602 (16)	0.2249 (2)	0.0633 (8)
O9	0.8490 (5)	0.2703 (3)	0.3497 (2)	0.1377 (17)
O10	0.8992 (3)	0.2700 (2)	0.2174 (2)	0.0809 (10)
O11	0.58719 (19)	0.35057 (16)	0.07275 (17)	0.0478 (5)
O12	0.6061 (3)	0.49507 (18)	0.1043 (2)	0.0779 (9)
O13	0.75861 (19)	0.41086 (15)	0.10619 (17)	0.0457 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0326 (14)	0.0304 (13)	0.0328 (14)	0.0001 (11)	0.0084 (11)	0.0008 (11)
C2	0.0338 (15)	0.0357 (14)	0.0341 (14)	−0.0031 (12)	0.0074 (12)	0.0002 (12)
C3	0.0492 (19)	0.0455 (18)	0.0374 (16)	0.0018 (15)	0.0022 (14)	0.0098 (13)
C4	0.062 (2)	0.052 (2)	0.0429 (18)	−0.0013 (17)	0.0104 (16)	0.0185 (15)
C5	0.052 (2)	0.0428 (17)	0.0477 (18)	−0.0078 (15)	0.0186 (16)	0.0115 (14)
C6	0.0382 (16)	0.0335 (14)	0.0408 (16)	−0.0030 (12)	0.0149 (13)	0.0017 (12)
C7	0.0350 (16)	0.0353 (15)	0.0528 (18)	−0.0075 (13)	0.0186 (14)	0.0013 (13)
C8	0.0262 (16)	0.0448 (19)	0.089 (3)	−0.0044 (14)	0.0089 (17)	−0.0001 (18)
C9	0.0259 (16)	0.059 (2)	0.067 (2)	−0.0044 (14)	0.0062 (15)	0.0024 (17)
C10	0.0306 (16)	0.0420 (17)	0.079 (2)	0.0051 (14)	0.0225 (16)	0.0063 (16)
C11	0.0298 (14)	0.0363 (14)	0.0340 (14)	0.0067 (12)	0.0052 (11)	0.0010 (12)
C12	0.0329 (14)	0.0304 (13)	0.0280 (13)	0.0012 (11)	0.0065 (11)	−0.0008 (10)
C13	0.0431 (17)	0.0323 (14)	0.0382 (16)	0.0068 (13)	0.0070 (13)	0.0022 (12)
C14	0.057 (2)	0.0283 (14)	0.0526 (19)	−0.0006 (14)	0.0135 (16)	0.0089 (13)
C15	0.0448 (18)	0.0352 (15)	0.0463 (17)	−0.0081 (13)	0.0145 (14)	0.0057 (13)
C16	0.0310 (14)	0.0312 (14)	0.0343 (14)	−0.0015 (11)	0.0072 (11)	0.0011 (11)
C17	0.0323 (14)	0.0268 (12)	0.0254 (12)	−0.0026 (11)	0.0054 (10)	−0.0005 (10)
C18	0.0374 (18)	0.061 (2)	0.077 (3)	−0.0020 (16)	0.0289 (18)	0.0201 (19)
C19	0.0328 (18)	0.084 (3)	0.069 (2)	−0.0063 (18)	−0.0103 (17)	0.024 (2)
Cu1	0.02206 (16)	0.03009 (16)	0.03997 (18)	−0.00026 (13)	0.00866 (14)	0.00474 (14)
Eu1	0.02169 (8)	0.02888 (8)	0.03354 (8)	−0.00131 (5)	0.00688 (5)	−0.00045 (5)
N1	0.0247 (12)	0.0372 (13)	0.0539 (15)	−0.0038 (10)	0.0110 (11)	−0.0005 (11)
N2	0.0254 (12)	0.0361 (13)	0.0422 (13)	0.0030 (10)	0.0103 (10)	0.0021 (10)
N3	0.0429 (16)	0.0409 (15)	0.0632 (18)	−0.0032 (12)	0.0008 (14)	−0.0151 (13)
N4	0.119 (4)	0.100 (3)	0.0346 (16)	0.079 (3)	−0.003 (2)	−0.0102 (17)
N5	0.0479 (17)	0.0361 (14)	0.0454 (15)	0.0078 (12)	0.0084 (12)	0.0007 (11)
O1	0.0274 (10)	0.0341 (10)	0.0457 (11)	0.0018 (8)	0.0107 (9)	0.0132 (9)
O2	0.0270 (10)	0.0460 (12)	0.0437 (12)	−0.0020 (9)	0.0002 (9)	0.0098 (9)
O3	0.0269 (10)	0.0276 (9)	0.0447 (11)	0.0020 (8)	0.0122 (8)	0.0073 (8)
O4	0.0310 (11)	0.0382 (11)	0.0521 (12)	−0.0011 (9)	0.0181 (10)	0.0089 (9)
O5	0.0432 (13)	0.0474 (13)	0.0544 (13)	−0.0019 (11)	0.0136 (11)	−0.0141 (11)
O6	0.068 (2)	0.087 (2)	0.151 (3)	−0.0302 (18)	0.010 (2)	−0.070 (2)
O7	0.0293 (11)	0.0483 (13)	0.0551 (13)	−0.0027 (9)	0.0066 (10)	−0.0091 (11)
O8	0.088 (2)	0.0581 (16)	0.0499 (15)	0.0195 (14)	0.0294 (16)	0.0010 (12)
O9	0.166 (4)	0.192 (4)	0.0457 (17)	0.115 (3)	−0.003 (2)	−0.020 (2)
O10	0.0621 (19)	0.114 (3)	0.0561 (17)	0.0386 (18)	−0.0146 (15)	−0.0300 (17)
O11	0.0298 (11)	0.0466 (13)	0.0674 (15)	0.0017 (10)	0.0107 (10)	−0.0029 (11)
O12	0.089 (2)	0.0437 (14)	0.099 (2)	0.0295 (15)	0.0140 (18)	−0.0063 (15)
O13	0.0378 (12)	0.0380 (12)	0.0607 (14)	−0.0067 (9)	0.0087 (10)	−0.0057 (10)

Geometric parameters (Å, º) top

C1—O1	1.337 (3)	C16—O4	1.380 (3)
C1—C6	1.398 (4)	C16—C17	1.409 (4)
C1—C2	1.398 (4)	C17—O3	1.329 (3)
C2—C3	1.378 (4)	C18—O4	1.445 (3)
C2—O2	1.383 (3)	C18—H15	0.9600
C3—C4	1.392 (5)	C18—H16	0.9600
C3—H1	0.9300	C18—H17	0.9600
C4—C5	1.363 (5)	C19—O2	1.433 (4)
C4—H2	0.9300	C19—H18	0.9600
C5—C6	1.414 (4)	C19—H19	0.9600
C5—H3	0.9300	C19—H20	0.9600
C6—C7	1.441 (4)	Cu1—O3	1.9315 (18)
C7—N1	1.278 (4)	Cu1—O1	1.9320 (19)
C7—H4	0.9300	Cu1—N2	1.940 (2)
C8—N1	1.494 (4)	Cu1—N1	1.980 (2)
C8—C9	1.501 (5)	Eu1—O1	2.3694 (19)
C8—H5	0.9700	Eu1—O3	2.4457 (18)
C8—H6	0.9700	Eu1—O13	2.466 (2)
C9—C10	1.502 (5)	Eu1—O7	2.470 (2)
C9—H7	0.9700	Eu1—O8	2.478 (3)
C9—H8	0.9700	Eu1—O10	2.478 (3)
C10—N2	1.478 (4)	Eu1—O5	2.480 (2)
C10—H9	0.9700	Eu1—O11	2.548 (2)
C10—H10	0.9700	Eu1—O4	2.584 (2)
C11—N2	1.281 (4)	Eu1—O2	2.593 (2)
C11—C12	1.445 (4)	N3—O6	1.198 (4)
C11—H11	0.9300	N3—O5	1.266 (4)
C12—C17	1.395 (4)	N3—O7	1.271 (3)
C12—C13	1.418 (4)	N4—O9	1.222 (5)
C13—C14	1.368 (4)	N4—O8	1.249 (5)
C13—H12	0.9300	N4—O10	1.256 (6)
C14—C15	1.387 (5)	N5—O12	1.216 (3)
C14—H13	0.9300	N5—O11	1.254 (3)
C15—C16	1.376 (4)	N5—O13	1.273 (3)
C15—H14	0.9300

O1—C1—C6	122.9 (3)	O1—Eu1—O3	61.31 (6)
O1—C1—C2	117.9 (2)	O1—Eu1—O13	79.49 (7)
C6—C1—C2	119.2 (3)	O3—Eu1—O13	125.96 (7)
C3—C2—O2	124.8 (3)	O1—Eu1—O7	135.09 (7)
C3—C2—C1	121.1 (3)	O3—Eu1—O7	116.46 (7)
O2—C2—C1	114.0 (2)	O13—Eu1—O7	117.56 (7)
C2—C3—C4	119.6 (3)	O1—Eu1—O8	134.09 (10)
C2—C3—H1	120.2	O3—Eu1—O8	107.21 (9)
C4—C3—H1	120.2	O13—Eu1—O8	73.82 (8)
C5—C4—C3	120.3 (3)	O7—Eu1—O8	90.65 (10)
C5—C4—H2	119.8	O1—Eu1—O10	85.77 (10)
C3—C4—H2	119.8	O3—Eu1—O10	68.91 (8)
C4—C5—C6	120.9 (3)	O13—Eu1—O10	72.77 (9)
C4—C5—H3	119.6	O7—Eu1—O10	137.83 (11)
C6—C5—H3	119.6	O8—Eu1—O10	51.04 (12)
C1—C6—C5	118.8 (3)	O1—Eu1—O5	88.53 (8)
C1—C6—C7	122.9 (3)	O3—Eu1—O5	76.02 (8)
C5—C6—C7	118.2 (3)	O13—Eu1—O5	141.92 (8)
N1—C7—C6	127.9 (3)	O7—Eu1—O5	51.56 (8)
N1—C7—H4	116.1	O8—Eu1—O5	134.29 (9)
C6—C7—H4	116.1	O10—Eu1—O5	142.67 (9)
N1—C8—C9	113.9 (3)	O1—Eu1—O11	119.29 (7)
N1—C8—H5	108.8	O3—Eu1—O11	174.77 (7)
C9—C8—H5	108.8	O13—Eu1—O11	50.70 (7)
N1—C8—H6	108.8	O7—Eu1—O11	67.17 (8)
C9—C8—H6	108.8	O8—Eu1—O11	68.45 (9)
H5—C8—H6	107.7	O10—Eu1—O11	105.86 (9)
C8—C9—C10	112.7 (3)	O5—Eu1—O11	109.04 (8)
C8—C9—H7	109.0	O1—Eu1—O4	123.26 (6)
C10—C9—H7	109.0	O3—Eu1—O4	62.20 (6)
C8—C9—H8	109.0	O13—Eu1—O4	142.41 (8)
C10—C9—H8	109.0	O7—Eu1—O4	69.64 (7)
H7—C9—H8	107.8	O8—Eu1—O4	69.12 (7)
N2—C10—C9	109.6 (3)	O10—Eu1—O4	79.18 (10)
N2—C10—H9	109.7	O5—Eu1—O4	73.38 (8)
C9—C10—H9	109.7	O11—Eu1—O4	117.46 (7)
N2—C10—H10	109.7	O1—Eu1—O2	62.67 (7)
C9—C10—H10	109.7	O3—Eu1—O2	114.81 (7)
H9—C10—H10	108.2	O13—Eu1—O2	70.45 (8)
N2—C11—C12	127.3 (3)	O7—Eu1—O2	83.38 (8)
N2—C11—H11	116.3	O8—Eu1—O2	135.61 (8)
C12—C11—H11	116.3	O10—Eu1—O2	134.86 (10)
C17—C12—C13	119.8 (3)	O5—Eu1—O2	71.93 (8)
C17—C12—C11	123.0 (2)	O11—Eu1—O2	68.74 (8)
C13—C12—C11	117.1 (3)	O4—Eu1—O2	144.61 (7)
C14—C13—C12	120.1 (3)	C7—N1—C8	114.6 (3)
C14—C13—H12	120.0	C7—N1—Cu1	122.6 (2)
C12—C13—H12	120.0	C8—N1—Cu1	122.8 (2)
C13—C14—C15	120.5 (3)	C11—N2—C10	117.0 (2)
C13—C14—H13	119.7	C11—N2—Cu1	124.85 (19)
C15—C14—H13	119.7	C10—N2—Cu1	118.15 (19)
C16—C15—C14	120.1 (3)	O6—N3—O5	121.1 (3)
C16—C15—H14	119.9	O6—N3—O7	122.8 (3)
C14—C15—H14	119.9	O5—N3—O7	116.1 (2)
C15—C16—O4	124.9 (3)	O9—N4—O8	121.7 (5)
C15—C16—C17	121.0 (3)	O9—N4—O10	121.3 (5)
O4—C16—C17	114.1 (2)	O8—N4—O10	117.0 (3)
O3—C17—C12	123.5 (2)	O12—N5—O11	123.3 (3)
O3—C17—C16	118.0 (2)	O12—N5—O13	120.2 (3)
C12—C17—C16	118.5 (2)	O11—N5—O13	116.5 (2)
O4—C18—H15	109.5	C1—O1—Cu1	124.84 (17)
O4—C18—H16	109.5	C1—O1—Eu1	124.78 (16)
H15—C18—H16	109.5	Cu1—O1—Eu1	110.09 (8)
O4—C18—H17	109.5	C2—O2—C19	117.1 (2)
H15—C18—H17	109.5	C2—O2—Eu1	116.77 (17)
H16—C18—H17	109.5	C19—O2—Eu1	126.1 (2)
O2—C19—H18	109.5	C17—O3—Cu1	127.52 (17)
O2—C19—H19	109.5	C17—O3—Eu1	125.29 (16)
H18—C19—H19	109.5	Cu1—O3—Eu1	107.10 (8)
O2—C19—H20	109.5	C16—O4—C18	116.2 (2)
H18—C19—H20	109.5	C16—O4—Eu1	120.07 (15)
H19—C19—H20	109.5	C18—O4—Eu1	123.57 (19)
O3—Cu1—O1	78.94 (8)	N3—O5—Eu1	95.64 (17)
O3—Cu1—N2	93.28 (9)	N3—O7—Eu1	95.94 (17)
O1—Cu1—N2	168.21 (10)	N4—O8—Eu1	96.1 (2)
O3—Cu1—N1	167.44 (9)	N4—O10—Eu1	95.9 (3)
O1—Cu1—N1	92.19 (9)	N5—O11—Eu1	94.71 (17)
N2—Cu1—N1	96.78 (10)	N5—O13—Eu1	98.11 (17)

Experimental details

Crystal data
Chemical formula	[CuEu(C₁₉H₂₀N₂O₄)(NO₃)₃]
M_r	741.90
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	11.638 (2), 14.680 (3), 14.853 (3)
β (°)	101.52 (3)
V (Å³)	2486.5 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.43
Crystal size (mm)	0.21 × 0.20 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.527, 0.568
No. of measured, independent and observed [I > 2σ(I)] reflections	23524, 5660, 5072
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.058, 1.06
No. of reflections	5660
No. of parameters	354
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.45

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

Acknowledgements

This work is supported financially by the National Natural Science Foundation of China (Nos. 20672032 and 20572018), the Key Laboratory of Heilongjiang Province and the Education Department of Heilongjiang Province (Nos. ZJG0504, JC200605, 1152GZD02 and 2006FRFLXG031).

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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