(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)samarium(III)

Sun, W.-B.; Yan, P.-F.; Li, H.-F.; Gao, T.; Li, G.-M.

doi:10.1107/S160053680902399X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m840-m841

doi:10.1107/S160053680902399X

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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)samarium(III)

Wen-Bin Sun,^a Peng-Fei Yan,^a Hong-Feng Li,^a Ting Gao ^a and Guang-Ming Li ^a ^*

^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
^*Correspondence e-mail: gmli@hlju.edu.cn

(Received 16 June 2009; accepted 23 June 2009; online 27 June 2009)

In the title heteronuclear complex, [CuSm(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 by an O atom from the acetone molecule in a square-pyramidal geometry. The Sm^III ion is ten-coordinated by six O atoms from the three nitrate ligands and four O atoms from the L ligand. In L, the C atoms of the diaminopropane fragment are disordered over two positions in a 0.674 (10):0.326 (10) ratio.

Related literature

For similar Cu–Ln (Ln = Gd, Pr and Tb) dinuclear complexes of the N,N′-bis(3-methoxysalicylidene)propane-1,2-diamine ligand, see: Kara et al. (2000 ); Sun et al. (2007 , 2009 ).

Experimental

Crystal data

[CuSm(C₁₉H₂₀N₂O₄)(NO₃)₃(C₃H₆O)]
M_r = 797.38
Monoclinic, P 2₁ /c
a = 9.882 (4) Å
b = 18.868 (5) Å
c = 15.631 (5) Å
β = 95.320 (16)°
V = 2901.9 (16) Å³
Z = 4
Mo Kα radiation
μ = 2.81 mm⁻¹
T = 291 K
0.39 × 0.33 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.404, T_max = 0.500 (expected range = 0.357–0.442)
28125 measured reflections
6634 independent reflections
5584 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.07
6634 reflections
421 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.74 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/S160053680902399X/cv2575sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902399X/cv2575Isup2.hkl

checkCIF report

Comment top

In continuation of our study of heteronuclear complexes of N,N'-bis(3- methoxysalicylidene)propane-1,2-diamine ligand (Sun et al., 2007, 2009), we present here the crystal structure of the title compound. As shown in Fig. 1, ligand L links Cu and Sm atoms into a dinuclear complex through two phenolate O atoms, and the Sm^III centre in the complex is ten-coordinated by four oxygen atoms from L and six oxygen atoms from three nitrato ions. 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. The title compound is isostructural with the previous Cu—Ln complexes (Ln = Gd, Pr and Tb) (Kara et al., 2000; Sun et al., 2007, 2009) derived from the same ligand.

Related literature top

For similar Cu–Ln (Ln = Gd, Pr and Tb) dinuclear complexes of the N,N'-bis(3-methoxysalicylidene)propane- 1,2-diamine ligand, see: Kara et al. (2000); Sun et al. (2007, 2009)

Experimental top

To a 1:1 MeOH/Me₂CO solution (20 ml) of the Schiff ligand (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 Sm(NO₃)₃6H₂O (0.105 g, 0.25 mmol) at ambient temperature. After stirring for 5 h, red solid was collected by filtration and washed with MeOH, [CuSm(C₁₉H₂₀N₂O₄)(CH₃COCH₃)(NO₃)₃], yield 0.180 g (87%). 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 C₂₂H₂₆CuN₅O₁₄Sm: C, 33.10; H, 3.28; N, 8.77; found: C, 33.01; H, 3.31; N, 8.92%.

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 40% probability displacement ellipsoids. Only major part of the disordered fragment is shown.

(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)samarium(III) top

Crystal data top

[CuSm(C₁₉H₂₀N₂O₄)(NO₃)₃(C₃H₆O)]	F(000) = 1580
M_r = 797.38	D_x = 1.825 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 23031 reflections
a = 9.882 (4) Å	θ = 3.0–27.5°
b = 18.868 (5) Å	µ = 2.81 mm⁻¹
c = 15.631 (5) Å	T = 291 K
β = 95.320 (16)°	Block, brown
V = 2901.9 (16) Å³	0.39 × 0.33 × 0.29 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	6634 independent reflections
Radiation source: fine-focus sealed tube	5584 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.404, T_max = 0.500	k = −24→24
28125 measured reflections	l = −19→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0469P)² + 1.8845P] where P = (F_o² + 2F_c²)/3
6634 reflections	(Δ/σ)_max = 0.006
421 parameters	Δρ_max = 1.03 e Å⁻³
36 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

[CuSm(C₁₉H₂₀N₂O₄)(NO₃)₃(C₃H₆O)]	V = 2901.9 (16) Å³
M_r = 797.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.882 (4) Å	µ = 2.81 mm⁻¹
b = 18.868 (5) Å	T = 291 K
c = 15.631 (5) Å	0.39 × 0.33 × 0.29 mm
β = 95.320 (16)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	6634 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5584 reflections with I > 2σ(I)
T_min = 0.404, T_max = 0.500	R_int = 0.031
28125 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	36 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.07	Δρ_max = 1.03 e Å⁻³
6634 reflections	Δρ_min = −0.74 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)
C8'	0.1263 (19)	0.1131 (8)	0.6707 (10)	0.071 (4)	0.326 (10)
H4'	0.0359	0.1213	0.6897	0.086*	0.326 (10)
C9'	0.145 (3)	0.0470 (10)	0.6393 (18)	0.150 (11)	0.326 (10)
H5A	0.1310	0.0479	0.5778	0.225*	0.326 (10)
H6A	0.0817	0.0149	0.6615	0.225*	0.326 (10)
H7A	0.2362	0.0315	0.6566	0.225*	0.326 (10)
C10'	0.1389 (17)	0.1317 (7)	0.5793 (11)	0.051 (4)	0.326 (10)
H8A	0.0701	0.1072	0.5421	0.061*	0.326 (10)
H9A	0.2277	0.1182	0.5631	0.061*	0.326 (10)
C8	0.1982 (10)	0.1147 (4)	0.6338 (6)	0.075 (2)	0.674 (10)
H4	0.1715	0.0691	0.6569	0.091*	0.674 (10)
C9	0.2955 (13)	0.1009 (7)	0.5751 (7)	0.129 (4)	0.674 (10)
H5	0.3049	0.1418	0.5397	0.193*	0.674 (10)
H6	0.2663	0.0612	0.5396	0.193*	0.674 (10)
H7	0.3815	0.0902	0.6062	0.193*	0.674 (10)
C10	0.0731 (13)	0.1457 (5)	0.5815 (8)	0.096 (4)	0.674 (10)
H8	0.0545	0.1216	0.5268	0.115*	0.674 (10)
H9	−0.0069	0.1437	0.6130	0.115*	0.674 (10)
Sm1	0.28473 (2)	0.426361 (8)	0.751802 (10)	0.03909 (7)
Cu	0.20496 (6)	0.25917 (2)	0.67412 (3)	0.05590 (14)
O1	0.3107 (3)	0.30109 (12)	0.76905 (17)	0.0528 (7)
O2	0.4514 (3)	0.37744 (13)	0.87833 (16)	0.0527 (7)
O3	0.1956 (3)	0.35392 (13)	0.63401 (16)	0.0525 (7)
O4	0.2338 (3)	0.48443 (14)	0.59859 (16)	0.0512 (6)
O5	0.4888 (3)	0.39591 (16)	0.6739 (2)	0.0659 (8)
O6	0.6496 (5)	0.4695 (2)	0.6546 (3)	0.1085 (16)
O7	0.4919 (3)	0.49733 (14)	0.7349 (2)	0.0609 (7)
O8	0.2232 (4)	0.55708 (17)	0.7635 (2)	0.0720 (10)
O9	0.2694 (5)	0.62299 (18)	0.8738 (3)	0.1104 (17)
O10	0.3179 (5)	0.51210 (16)	0.87669 (19)	0.0808 (11)
O11	0.1305 (5)	0.3903 (3)	0.8594 (3)	0.0988 (13)
O12	−0.0836 (5)	0.4062 (3)	0.8508 (4)	0.132 (2)
O13	0.0338 (4)	0.4383 (2)	0.7491 (3)	0.0904 (12)
O14	−0.0249 (4)	0.25774 (19)	0.7448 (2)	0.0749 (9)
N1	0.2387 (5)	0.16408 (19)	0.7111 (3)	0.0851 (14)
N2	0.1181 (5)	0.2182 (2)	0.5703 (3)	0.0780 (13)
N3	0.5473 (4)	0.45422 (18)	0.6863 (2)	0.0566 (8)
N4	0.2711 (4)	0.56584 (17)	0.8385 (2)	0.0606 (10)
N5	0.0199 (5)	0.4123 (2)	0.8212 (3)	0.0754 (12)
C1	0.3693 (4)	0.26602 (18)	0.8360 (3)	0.0465 (8)
C2	0.4440 (4)	0.30587 (19)	0.8984 (2)	0.0494 (9)
C3	0.5035 (5)	0.2754 (3)	0.9723 (3)	0.0700 (13)
H1	0.5525	0.3028	1.0138	0.084*
C4	0.4889 (6)	0.2021 (3)	0.9838 (4)	0.0815 (16)
H2	0.5252	0.1809	1.0346	0.098*
C5	0.4224 (5)	0.1622 (2)	0.9217 (4)	0.0770 (15)
H3	0.4164	0.1135	0.9298	0.092*
C6	0.3628 (4)	0.1918 (2)	0.8460 (3)	0.0559 (10)
C7	0.3007 (5)	0.1443 (2)	0.7817 (4)	0.0759 (15)
C11	0.0826 (6)	0.2515 (3)	0.5020 (3)	0.0829 (16)
H10	0.0442	0.2253	0.4555	0.099*
C12	0.0966 (5)	0.3270 (3)	0.4898 (3)	0.0638 (12)
C13	0.0536 (5)	0.3555 (4)	0.4084 (3)	0.0800 (16)
H11	0.0141	0.3258	0.3656	0.096*
C14	0.0686 (6)	0.4248 (3)	0.3915 (3)	0.0792 (16)
H12	0.0377	0.4423	0.3375	0.095*
C15	0.1281 (5)	0.4698 (3)	0.4517 (2)	0.0652 (12)
H13	0.1398	0.5174	0.4387	0.078*
C16	0.1710 (4)	0.4441 (2)	0.5324 (2)	0.0508 (9)
C17	0.1542 (4)	0.3732 (2)	0.5535 (2)	0.0511 (9)
C18	0.2810 (6)	0.5531 (2)	0.5755 (3)	0.0662 (12)
H14	0.2046	0.5825	0.5569	0.099*
H15	0.3388	0.5484	0.5298	0.099*
H16	0.3311	0.5744	0.6245	0.099*
C19	0.5576 (6)	0.4172 (2)	0.9257 (3)	0.0725 (14)
H17	0.5695	0.4616	0.8975	0.109*
H18	0.6409	0.3907	0.9283	0.109*
H19	0.5335	0.4257	0.9829	0.109*
C20	−0.2540 (7)	0.2557 (4)	0.7781 (5)	0.108 (2)
H20	−0.3030	0.2983	0.7886	0.162*
H21	−0.2161	0.2362	0.8319	0.162*
H22	−0.3149	0.2218	0.7493	0.162*
C21	−0.1422 (5)	0.2722 (2)	0.7232 (3)	0.0635 (11)
C22	−0.1820 (6)	0.3064 (3)	0.6394 (4)	0.0856 (16)
H23	−0.2482	0.3426	0.6467	0.128*
H24	−0.2203	0.2715	0.5995	0.128*
H25	−0.1035	0.3272	0.6177	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8'	0.072 (5)	0.071 (5)	0.072 (5)	−0.0003 (10)	0.0066 (11)	−0.0003 (10)
C9'	0.158 (14)	0.134 (13)	0.159 (14)	−0.015 (9)	0.018 (9)	0.004 (9)
C10'	0.056 (7)	0.029 (5)	0.069 (7)	−0.006 (5)	0.015 (6)	−0.023 (5)
C8	0.077 (2)	0.073 (2)	0.076 (2)	−0.0005 (10)	0.0069 (10)	−0.0024 (10)
C9	0.129 (5)	0.128 (4)	0.129 (4)	0.0003 (10)	0.0126 (11)	−0.0001 (10)
C10	0.101 (9)	0.075 (6)	0.107 (7)	0.005 (6)	−0.011 (7)	−0.049 (5)
Sm1	0.04727 (12)	0.03289 (10)	0.03616 (10)	−0.00080 (7)	−0.00128 (7)	−0.00168 (6)
Cu	0.0668 (3)	0.0395 (2)	0.0598 (3)	−0.0081 (2)	−0.0022 (2)	−0.0138 (2)
O1	0.0649 (19)	0.0321 (11)	0.0580 (15)	−0.0026 (11)	−0.0123 (13)	0.0002 (10)
O2	0.0618 (18)	0.0416 (12)	0.0507 (14)	−0.0020 (12)	−0.0166 (13)	0.0029 (11)
O3	0.0677 (19)	0.0485 (14)	0.0396 (13)	−0.0129 (13)	−0.0046 (12)	−0.0065 (10)
O4	0.0583 (17)	0.0523 (14)	0.0421 (13)	−0.0003 (12)	−0.0003 (12)	0.0079 (11)
O5	0.065 (2)	0.0495 (15)	0.085 (2)	−0.0083 (14)	0.0213 (17)	−0.0209 (15)
O6	0.092 (3)	0.073 (2)	0.172 (4)	−0.019 (2)	0.074 (3)	−0.014 (3)
O7	0.0613 (19)	0.0437 (14)	0.0786 (19)	−0.0055 (13)	0.0112 (15)	−0.0144 (13)
O8	0.099 (3)	0.0538 (16)	0.0581 (17)	0.0220 (17)	−0.0187 (17)	−0.0100 (13)
O9	0.175 (5)	0.0548 (19)	0.092 (3)	0.032 (2)	−0.038 (3)	−0.0323 (18)
O10	0.134 (3)	0.0544 (17)	0.0495 (16)	0.0307 (19)	−0.0160 (18)	−0.0106 (13)
O11	0.080 (3)	0.139 (4)	0.081 (3)	0.004 (3)	0.028 (2)	0.038 (3)
O12	0.087 (3)	0.167 (5)	0.151 (5)	0.000 (3)	0.069 (4)	−0.007 (4)
O13	0.061 (2)	0.117 (3)	0.093 (3)	0.005 (2)	0.008 (2)	0.022 (2)
O14	0.060 (2)	0.082 (2)	0.082 (2)	0.0122 (17)	0.0029 (18)	0.0157 (17)
N1	0.091 (3)	0.0357 (18)	0.124 (4)	−0.0006 (19)	−0.016 (3)	−0.015 (2)
N2	0.093 (3)	0.071 (2)	0.070 (3)	−0.030 (2)	0.010 (2)	−0.036 (2)
N3	0.056 (2)	0.0450 (17)	0.070 (2)	−0.0027 (16)	0.0151 (18)	0.0000 (16)
N4	0.078 (3)	0.0443 (17)	0.057 (2)	0.0107 (16)	−0.0078 (19)	−0.0121 (14)
N5	0.070 (3)	0.074 (3)	0.087 (3)	−0.008 (2)	0.032 (3)	−0.007 (2)
C1	0.043 (2)	0.0379 (17)	0.059 (2)	0.0019 (14)	0.0029 (17)	0.0066 (15)
C2	0.044 (2)	0.0475 (19)	0.055 (2)	0.0063 (16)	−0.0028 (17)	0.0117 (16)
C3	0.067 (3)	0.068 (3)	0.071 (3)	0.003 (2)	−0.016 (2)	0.015 (2)
C4	0.072 (3)	0.074 (3)	0.095 (4)	0.007 (3)	−0.011 (3)	0.044 (3)
C5	0.054 (3)	0.050 (2)	0.126 (5)	0.004 (2)	0.001 (3)	0.033 (3)
C6	0.041 (2)	0.0401 (18)	0.086 (3)	0.0040 (16)	0.004 (2)	0.0095 (18)
C7	0.062 (3)	0.0345 (19)	0.129 (5)	0.0030 (19)	−0.003 (3)	0.000 (2)
C11	0.087 (4)	0.105 (4)	0.056 (3)	−0.030 (3)	0.004 (3)	−0.038 (3)
C12	0.054 (3)	0.092 (3)	0.045 (2)	−0.011 (2)	0.0046 (18)	−0.021 (2)
C13	0.062 (3)	0.133 (5)	0.042 (2)	−0.006 (3)	−0.007 (2)	−0.023 (3)
C14	0.060 (3)	0.135 (5)	0.041 (2)	0.010 (3)	−0.005 (2)	0.000 (3)
C15	0.054 (3)	0.100 (3)	0.042 (2)	0.015 (2)	0.0065 (19)	0.009 (2)
C16	0.045 (2)	0.072 (2)	0.0357 (17)	0.0054 (18)	0.0040 (15)	0.0003 (16)
C17	0.047 (2)	0.071 (2)	0.0347 (17)	−0.0033 (18)	0.0016 (15)	−0.0089 (16)
C18	0.077 (3)	0.059 (2)	0.063 (3)	−0.004 (2)	0.009 (2)	0.019 (2)
C19	0.079 (3)	0.056 (2)	0.075 (3)	−0.011 (2)	−0.033 (3)	−0.001 (2)
C20	0.077 (4)	0.131 (6)	0.122 (5)	−0.005 (4)	0.033 (4)	0.010 (5)
C21	0.055 (3)	0.058 (2)	0.078 (3)	0.003 (2)	0.006 (2)	−0.001 (2)
C22	0.065 (3)	0.092 (4)	0.097 (4)	0.017 (3)	−0.005 (3)	0.012 (3)

Geometric parameters (Å, º) top

C8'—C9'	1.358 (10)	O8—N4	1.234 (4)
C8'—C10'	1.49 (2)	O9—N4	1.212 (4)
C8'—N1	1.559 (17)	O10—N4	1.243 (4)
C8'—H4'	0.9800	O11—N5	1.266 (6)
C9'—H5A	0.9600	O12—N5	1.166 (5)
C9'—H6A	0.9600	O13—N5	1.249 (6)
C9'—H7A	0.9600	O14—C21	1.208 (6)
C10'—N2	1.648 (15)	N1—C7	1.267 (7)
C10'—H8A	0.9700	N2—C11	1.261 (7)
C10'—H9A	0.9700	C1—C2	1.388 (5)
C8—C9	1.414 (9)	C1—C6	1.412 (5)
C8—C10	1.533 (15)	C2—C3	1.373 (5)
C8—N1	1.549 (9)	C3—C4	1.405 (7)
C8—H4	0.9800	C3—H1	0.9300
C9—H5	0.9600	C4—C5	1.350 (8)
C9—H6	0.9600	C4—H2	0.9300
C9—H7	0.9600	C5—C6	1.389 (6)
C10—N2	1.455 (12)	C5—H3	0.9300
C10—H8	0.9700	C6—C7	1.441 (7)
C10—H9	0.9700	C11—C12	1.444 (8)
Sm1—O1	2.390 (2)	C11—H10	0.9300
Sm1—O3	2.394 (2)	C12—C17	1.404 (5)
Sm1—O11	2.467 (4)	C12—C13	1.410 (7)
Sm1—O7	2.481 (3)	C13—C14	1.346 (8)
Sm1—O13	2.486 (4)	C13—H11	0.9300
Sm1—O5	2.517 (3)	C14—C15	1.361 (7)
Sm1—O10	2.533 (3)	C14—H12	0.9300
Sm1—O8	2.551 (3)	C15—C16	1.380 (5)
Sm1—O2	2.621 (3)	C15—H13	0.9300
Sm1—O4	2.639 (3)	C16—C17	1.392 (6)
Sm1—Cu	3.4452 (9)	C18—H14	0.9600
Cu—O3	1.894 (3)	C18—H15	0.9600
Cu—N1	1.905 (4)	C18—H16	0.9600
Cu—O1	1.906 (3)	C19—H17	0.9600
Cu—N2	1.926 (4)	C19—H18	0.9600
Cu—O14	2.616 (4)	C19—H19	0.9600
O1—C1	1.325 (4)	C20—C21	1.495 (8)
O2—C2	1.390 (4)	C20—H20	0.9600
O2—C19	1.438 (5)	C20—H21	0.9600
O3—C17	1.337 (4)	C20—H22	0.9600
O4—C16	1.384 (5)	C21—C22	1.479 (7)
O4—C18	1.435 (5)	C22—H23	0.9600
O5—N3	1.250 (5)	C22—H24	0.9600
O6—N3	1.202 (5)	C22—H25	0.9600
O7—N3	1.271 (4)

C9'—C8'—C10'	81.1 (16)	C2—O2—Sm1	118.0 (2)
C9'—C8'—N1	126.6 (19)	C19—O2—Sm1	125.6 (2)
C10'—C8'—N1	97.1 (12)	C17—O3—Cu	124.7 (2)
C9'—C8'—H4'	114.5	C17—O3—Sm1	128.8 (2)
C10'—C8'—H4'	114.5	Cu—O3—Sm1	106.33 (11)
N1—C8'—H4'	114.5	C16—O4—C18	116.3 (3)
C8'—C9'—H5A	109.4	C16—O4—Sm1	119.0 (2)
C8'—C9'—H6A	109.4	C18—O4—Sm1	124.3 (2)
H5A—C9'—H6A	109.5	N3—O5—Sm1	96.0 (2)
C8'—C9'—H7A	109.6	N3—O7—Sm1	97.1 (2)
H5A—C9'—H7A	109.5	N4—O8—Sm1	97.2 (2)
H6A—C9'—H7A	109.5	N4—O10—Sm1	97.8 (2)
C8'—C10'—N2	107.2 (10)	N5—O11—Sm1	98.6 (3)
C8'—C10'—H8A	110.3	N5—O13—Sm1	98.2 (3)
N2—C10'—H8A	110.3	C21—O14—Cu	136.6 (3)
C8'—C10'—H9A	110.3	C7—N1—C8	124.8 (5)
N2—C10'—H9A	110.3	C7—N1—C8'	116.1 (7)
H8A—C10'—H9A	108.5	C8—N1—C8'	35.8 (6)
C9—C8—C10	106.7 (10)	C7—N1—Cu	126.8 (3)
C9—C8—N1	118.4 (8)	C8—N1—Cu	107.7 (4)
C10—C8—N1	109.0 (6)	C8'—N1—Cu	111.1 (6)
C9—C8—H4	107.4	C11—N2—C10	120.5 (6)
C10—C8—H4	107.4	C11—N2—C10'	126.1 (7)
N1—C8—H4	107.4	C10—N2—C10'	25.3 (6)
N2—C10—C8	100.5 (8)	C11—N2—Cu	125.5 (3)
N2—C10—H8	111.7	C10—N2—Cu	113.2 (5)
C8—C10—H8	111.7	C10'—N2—Cu	106.4 (7)
N2—C10—H9	111.7	O6—N3—O5	122.8 (4)
C8—C10—H9	111.7	O6—N3—O7	121.2 (4)
H8—C10—H9	109.4	O5—N3—O7	115.9 (3)
O1—Sm1—O3	63.26 (9)	O9—N4—O8	122.1 (4)
O1—Sm1—O11	73.56 (14)	O9—N4—O10	121.8 (4)
O3—Sm1—O11	99.22 (14)	O8—N4—O10	116.1 (3)
O1—Sm1—O7	117.70 (10)	O12—N5—O13	124.8 (6)
O3—Sm1—O7	118.33 (10)	O12—N5—O11	122.1 (6)
O11—Sm1—O7	142.13 (14)	O13—N5—O11	113.1 (4)
O1—Sm1—O13	100.85 (12)	O1—C1—C2	116.7 (3)
O3—Sm1—O13	75.16 (13)	O1—C1—C6	124.2 (4)
O11—Sm1—O13	50.10 (14)	C2—C1—C6	119.1 (4)
O7—Sm1—O13	141.33 (11)	C3—C2—C1	121.5 (4)
O1—Sm1—O5	75.31 (10)	C3—C2—O2	124.7 (4)
O3—Sm1—O5	75.62 (10)	C1—C2—O2	113.8 (3)
O11—Sm1—O5	147.14 (14)	C2—C3—C4	118.7 (5)
O7—Sm1—O5	50.62 (9)	C2—C3—H1	120.7
O13—Sm1—O5	148.77 (13)	C4—C3—H1	120.7
O1—Sm1—O10	122.67 (9)	C5—C4—C3	120.4 (4)
O3—Sm1—O10	165.75 (12)	C5—C4—H2	119.8
O11—Sm1—O10	72.23 (16)	C3—C4—H2	119.8
O7—Sm1—O10	71.85 (12)	C4—C5—C6	121.9 (4)
O13—Sm1—O10	90.71 (15)	C4—C5—H3	119.1
O5—Sm1—O10	117.81 (13)	C6—C5—H3	119.1
O1—Sm1—O8	166.37 (12)	C5—C6—C1	118.3 (4)
O3—Sm1—O8	122.28 (10)	C5—C6—C7	117.6 (4)
O11—Sm1—O8	92.93 (15)	C1—C6—C7	124.1 (4)
O7—Sm1—O8	71.98 (12)	N1—C7—C6	124.4 (4)
O13—Sm1—O8	70.68 (14)	N2—C11—C12	125.5 (4)
O5—Sm1—O8	117.56 (12)	N2—C11—H10	117.2
O10—Sm1—O8	48.83 (10)	C12—C11—H10	117.2
O1—Sm1—O2	60.88 (8)	C17—C12—C13	118.1 (5)
O3—Sm1—O2	122.66 (9)	C17—C12—C11	123.8 (4)
O11—Sm1—O2	76.89 (13)	C13—C12—C11	118.1 (4)
O7—Sm1—O2	78.67 (10)	C14—C13—C12	121.2 (5)
O13—Sm1—O2	126.90 (12)	C14—C13—H11	119.4
O5—Sm1—O2	79.01 (11)	C12—C13—H11	119.4
O10—Sm1—O2	67.43 (9)	C13—C14—C15	121.3 (5)
O8—Sm1—O2	115.05 (9)	C13—C14—H12	119.4
O1—Sm1—O4	121.49 (9)	C15—C14—H12	119.4
O3—Sm1—O4	60.90 (9)	C14—C15—C16	119.3 (5)
O11—Sm1—O4	130.92 (13)	C14—C15—H13	120.3
O7—Sm1—O4	76.65 (10)	C16—C15—H13	120.3
O13—Sm1—O4	80.85 (12)	C15—C16—O4	124.6 (4)
O5—Sm1—O4	75.50 (11)	C15—C16—C17	121.4 (4)
O10—Sm1—O4	115.74 (9)	O4—C16—C17	114.0 (3)
O8—Sm1—O4	68.73 (9)	O3—C17—C16	116.8 (3)
O2—Sm1—O4	152.18 (10)	O3—C17—C12	124.6 (4)
O1—Sm1—Cu	32.10 (6)	C16—C17—C12	118.6 (4)
O3—Sm1—Cu	31.84 (6)	O4—C18—H14	109.5
O11—Sm1—Cu	81.50 (12)	O4—C18—H15	109.5
O7—Sm1—Cu	128.37 (6)	H14—C18—H15	109.5
O13—Sm1—Cu	83.23 (11)	O4—C18—H16	109.5
O5—Sm1—Cu	77.75 (7)	H14—C18—H16	109.5
O10—Sm1—Cu	149.93 (8)	H15—C18—H16	109.5
O8—Sm1—Cu	149.58 (8)	O2—C19—H17	109.5
O2—Sm1—Cu	92.91 (6)	O2—C19—H18	109.5
O4—Sm1—Cu	92.42 (6)	H17—C19—H18	109.5
O3—Cu—N1	172.44 (19)	O2—C19—H19	109.5
O3—Cu—O1	82.66 (11)	H17—C19—H19	109.5
N1—Cu—O1	94.96 (16)	H18—C19—H19	109.5
O3—Cu—N2	95.50 (16)	C21—C20—H20	109.5
N1—Cu—N2	86.0 (2)	C21—C20—H21	109.5
O1—Cu—N2	172.76 (17)	H20—C20—H21	109.5
O3—Cu—O14	97.58 (12)	C21—C20—H22	109.5
N1—Cu—O14	89.80 (18)	H20—C20—H22	109.5
O1—Cu—O14	96.32 (13)	H21—C20—H22	109.5
N2—Cu—O14	90.86 (17)	O14—C21—C22	121.1 (5)
O3—Cu—Sm1	41.83 (7)	O14—C21—C20	122.2 (5)
N1—Cu—Sm1	136.67 (14)	C22—C21—C20	116.7 (5)
O1—Cu—Sm1	41.80 (7)	C21—C22—H23	109.5
N2—Cu—Sm1	137.23 (14)	C21—C22—H24	109.5
O14—Cu—Sm1	92.28 (8)	H23—C22—H24	109.5
C1—O1—Cu	125.1 (2)	C21—C22—H25	109.5
C1—O1—Sm1	128.1 (2)	H23—C22—H25	109.5
Cu—O1—Sm1	106.11 (11)	H24—C22—H25	109.5
C2—O2—C19	116.2 (3)

Experimental details

Crystal data
Chemical formula	[CuSm(C₁₉H₂₀N₂O₄)(NO₃)₃(C₃H₆O)]
M_r	797.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	9.882 (4), 18.868 (5), 15.631 (5)
β (°)	95.320 (16)
V (Å³)	2901.9 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.81
Crystal size (mm)	0.39 × 0.33 × 0.29

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.404, 0.500
No. of measured, independent and observed [I > 2σ(I)] reflections	28125, 6634, 5584
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.07
No. of reflections	6634
No. of parameters	421
No. of restraints	36
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −0.74

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
Sun, W.-B., Yan, P.-F., Li, G.-M. & Hou, G.-F. (2009). Acta Cryst. E65, m780–m781. Web of Science CSD CrossRef IUCr Journals Google Scholar

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