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

Wang, J.-H.; Gao, P.; Yan, P.-F.; Li, G.-M.; Hou, G.-F.

doi:10.1107/S1600536807061454

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m344

doi:10.1107/S1600536807061454

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

Jing-Hua Wang,^a Po Gao,^a Peng-Fei Yan,^a Guang-Ming Li ^a ^* and Guang-Feng Hou ^a

^aSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: gmli@hlju.edu.cn

(Received 21 November 2007; accepted 21 November 2007; online 16 January 2008)

In the title complex, [CuSm(C₁₉H₂₀N₂O₄)(NO₃)₃]·CH₃CO-CH₃, the Cu^II atom is four-coordinated in a square-planar geometry by two O atoms and two N atoms of the deprotonated Schiff base. The Sm^III atom is ten-coordinate, chelated by three nitrate groups and linked to the four O atoms of the deprotonated Schiff base.

Related literature

See Elmali & Elerman (2003 , 2004 ) for similar copper–lanthanum complexes of the same Schiff base.

Experimental

Crystal data

[CuSm(C₁₉H₂₀N₂O₄)(NO₃)₃]·C₃H₆O
M_r = 798.37
Triclinic, $[P \overline 1]$
a = 9.384 (5) Å
b = 12.111 (5) Å
c = 13.529 (6) Å
α = 73.071 (18)°
β = 86.984 (19)°
γ = 72.346 (18)°
V = 1400.5 (11) Å³
Z = 2
Mo Kα radiation
μ = 2.91 mm⁻¹
T = 295 (2) K
0.33 × 0.30 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.446, T_max = 0.610 (expected range = 0.420–0.575)
13938 measured reflections
6381 independent reflections
5692 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.062
S = 1.09
6381 reflections
392 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061454/ng2393sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807061454/ng2393Isup2.hkl

checkCIF report

Comment top

As shown in Fig. 1, the octodentate Schiff base ligand links Cu and Sm atoms into a dinuclear complex through two phenolate O atoms, which is similar with the bonding reported for another copper-lanthanum complex of the same ligand (Elmali & Elerman, 2003, 2004). The Sm^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. And one molecular acetone is dissociative in the complex.

Related literature top

See Elmali & Elerman (2003, 2004) for similar copper–lanthanum complexes of the same Schiff base.

Experimental top

The title complex was obtained by the treatment of copper(II) acetate monohydrate with the Schiff base in methanol/acetone (4:1) at room temperature. Then the mixture was refluxed for 3 h after the addition of samarium (III) nitrate hexahydrate. 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 C₂₂H₂₆CuN₅O₁₄Sm: C, 33.28; H, 3.12; Cu, 7.91; N, 8.88; Sm, 18.86; found: C, 33.10; H, 3.28; Cu, 7.96; N, 8.77; Sm, 18.83%.

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).

Figures top

Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids. All H atoms and actone molecule have been omitted for clarity.

{µ-6,6'-Dimethoxy-2,2'-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato}τrinitratocopper(II)samarium(III) acetone solvate top

Crystal data top

[CuSm(C₁₉H₂₀N₂O₄)(NO₃)₃]·C₃H₆O	Z = 2
M_r = 798.37	F(000) = 792
Triclinic, P1	D_x = 1.893 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.384 (5) Å	Cell parameters from 12555 reflections
b = 12.111 (5) Å	θ = 6.3–55.0°
c = 13.529 (6) Å	µ = 2.91 mm⁻¹
α = 73.071 (18)°	T = 295 K
β = 86.984 (19)°	Block, green
γ = 72.346 (18)°	0.33 × 0.30 × 0.19 mm
V = 1400.5 (11) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	6381 independent reflections
Radiation source: fine-focus sealed tube	5692 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scan	θ_max = 27.7°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.446, T_max = 0.610	k = −15→15
13938 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0234P)² + 0.9589P] where P = (F_o² + 2F_c²)/3
6381 reflections	(Δ/σ)_max = 0.001
392 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[CuSm(C₁₉H₂₀N₂O₄)(NO₃)₃]·C₃H₆O	γ = 72.346 (18)°
M_r = 798.37	V = 1400.5 (11) Å³
Triclinic, P1	Z = 2
a = 9.384 (5) Å	Mo Kα radiation
b = 12.111 (5) Å	µ = 2.91 mm⁻¹
c = 13.529 (6) Å	T = 295 K
α = 73.071 (18)°	0.33 × 0.30 × 0.19 mm
β = 86.984 (19)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	6381 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5692 reflections with I > 2σ(I)
T_min = 0.446, T_max = 0.610	R_int = 0.023
13938 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.09	Δρ_max = 0.57 e Å⁻³
6381 reflections	Δρ_min = −0.41 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	0.5501 (3)	0.7332 (2)	0.4170 (2)	0.0360 (6)
C2	0.6420 (3)	0.7711 (2)	0.3375 (2)	0.0380 (6)
C3	0.7936 (3)	0.7349 (3)	0.3504 (3)	0.0465 (7)
H1	0.8522	0.7622	0.2969	0.056*
C4	0.8598 (4)	0.6566 (3)	0.4449 (3)	0.0537 (9)
H2	0.9634	0.6310	0.4546	0.064*
C5	0.7740 (4)	0.6175 (3)	0.5226 (3)	0.0527 (8)
H3	0.8195	0.5648	0.5852	0.063*
C6	0.6162 (3)	0.6554 (3)	0.5105 (2)	0.0422 (7)
C7	0.5318 (4)	0.6060 (3)	0.5936 (2)	0.0490 (8)
H4	0.5879	0.5478	0.6504	0.059*
C8	0.3395 (5)	0.5602 (4)	0.6970 (3)	0.0819 (14)
H5	0.3455	0.5953	0.7520	0.098*
H6	0.4067	0.4780	0.7162	0.098*
C9	0.1820 (5)	0.5565 (3)	0.6872 (3)	0.0663 (11)
H7	0.1718	0.5328	0.6260	0.080*
H8	0.1627	0.4960	0.7468	0.080*
C10	0.0698 (4)	0.6750 (3)	0.6799 (2)	0.0538 (8)
H9	−0.0281	0.6636	0.6933	0.065*
H10	0.0937	0.7071	0.7326	0.065*
C11	−0.0655 (3)	0.8406 (3)	0.5481 (2)	0.0424 (7)
H11	−0.1403	0.8359	0.5956	0.051*
C12	−0.1089 (3)	0.9324 (3)	0.4522 (2)	0.0384 (6)
C13	−0.2583 (4)	1.0074 (3)	0.4383 (3)	0.0497 (8)
H12	−0.3221	0.9999	0.4932	0.060*
C14	−0.3108 (4)	1.0906 (3)	0.3460 (3)	0.0533 (8)
H13	−0.4098	1.1394	0.3381	0.064*
C15	−0.2161 (3)	1.1026 (3)	0.2633 (3)	0.0470 (7)
H14	−0.2519	1.1588	0.1998	0.056*
C16	−0.0682 (3)	1.0303 (2)	0.2762 (2)	0.0376 (6)
C17	−0.0128 (3)	0.9440 (2)	0.3701 (2)	0.0340 (6)
C18	−0.0188 (4)	1.1099 (3)	0.0970 (3)	0.0576 (9)
H15	−0.0858	1.0772	0.0718	0.086*
H16	0.0640	1.1107	0.0523	0.086*
H17	−0.0709	1.1909	0.0983	0.086*
C19	0.6504 (4)	0.8849 (4)	0.1599 (3)	0.0568 (9)
H18	0.7168	0.9218	0.1802	0.085*
H19	0.5843	0.9427	0.1042	0.085*
H20	0.7078	0.8167	0.1376	0.085*
C20	0.1935 (7)	0.3884 (5)	−0.0090 (5)	0.1100 (19)
H21	0.1201	0.4099	−0.0636	0.165*
H22	0.1525	0.3581	0.0562	0.165*
H23	0.2805	0.3270	−0.0197	0.165*
C21	0.2360 (6)	0.4971 (4)	−0.0088 (4)	0.0800 (13)
C22	0.3365 (7)	0.4818 (5)	0.0816 (4)	0.1022 (18)
H24	0.3632	0.5547	0.0722	0.153*
H25	0.4256	0.4154	0.0852	0.153*
H26	0.2844	0.4658	0.1447	0.153*
Cu2	0.24465 (4)	0.75758 (3)	0.49629 (3)	0.03670 (8)
N1	0.3895 (3)	0.6310 (2)	0.60036 (19)	0.0498 (7)
N2	0.0646 (3)	0.7631 (2)	0.57760 (18)	0.0402 (5)
N3	0.3263 (3)	1.1105 (2)	0.2284 (2)	0.0510 (7)
N4	0.3808 (3)	0.8126 (3)	0.0426 (2)	0.0478 (6)
N5	0.1427 (3)	0.6889 (3)	0.2369 (2)	0.0528 (7)
O1	0.4021 (2)	0.77107 (19)	0.39863 (15)	0.0439 (5)
O2	0.5643 (2)	0.84507 (19)	0.24634 (16)	0.0447 (5)
O3	0.1281 (2)	0.87450 (18)	0.37652 (15)	0.0411 (5)
O4	0.0358 (2)	1.03583 (18)	0.20020 (16)	0.0436 (5)
O5	0.3167 (3)	1.0333 (2)	0.31093 (18)	0.0543 (6)
O6	0.3339 (4)	1.2091 (2)	0.2275 (2)	0.0787 (9)
O7	0.3255 (3)	1.0798 (2)	0.14667 (18)	0.0535 (6)
O8	0.3018 (3)	0.9182 (2)	0.04383 (17)	0.0524 (5)
O9	0.4101 (3)	0.7863 (3)	−0.0366 (2)	0.0736 (8)
O10	0.4267 (3)	0.7385 (2)	0.12933 (19)	0.0545 (6)
O11	0.0985 (3)	0.7954 (2)	0.1774 (2)	0.0568 (6)
O12	0.0852 (4)	0.6118 (3)	0.2345 (3)	0.0822 (9)
O13	0.2480 (3)	0.6667 (2)	0.2982 (2)	0.0590 (6)
O14	0.2011 (5)	0.5883 (3)	−0.0775 (3)	0.1208 (15)
Sm1	0.286846 (16)	0.877380 (13)	0.233252 (11)	0.03533 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0338 (14)	0.0327 (13)	0.0389 (14)	−0.0044 (11)	−0.0040 (11)	−0.0115 (12)
C2	0.0372 (15)	0.0340 (13)	0.0426 (15)	−0.0094 (11)	−0.0013 (12)	−0.0117 (12)
C3	0.0372 (16)	0.0438 (16)	0.063 (2)	−0.0129 (13)	0.0002 (14)	−0.0205 (16)
C4	0.0359 (16)	0.0490 (18)	0.075 (2)	−0.0042 (14)	−0.0133 (16)	−0.0223 (18)
C5	0.0488 (19)	0.0469 (17)	0.055 (2)	0.0011 (14)	−0.0207 (16)	−0.0163 (16)
C6	0.0437 (16)	0.0355 (14)	0.0418 (16)	−0.0010 (12)	−0.0114 (13)	−0.0120 (13)
C7	0.054 (2)	0.0409 (15)	0.0349 (15)	0.0064 (14)	−0.0118 (14)	−0.0049 (13)
C8	0.084 (3)	0.067 (2)	0.045 (2)	0.009 (2)	0.012 (2)	0.0240 (18)
C9	0.112 (4)	0.0417 (17)	0.0437 (19)	−0.033 (2)	0.014 (2)	−0.0017 (15)
C10	0.060 (2)	0.065 (2)	0.0346 (16)	−0.0272 (17)	0.0042 (14)	−0.0029 (15)
C11	0.0416 (16)	0.0494 (16)	0.0441 (16)	−0.0206 (13)	0.0115 (13)	−0.0198 (14)
C12	0.0362 (15)	0.0393 (14)	0.0442 (16)	−0.0129 (12)	0.0015 (12)	−0.0174 (13)
C13	0.0403 (17)	0.0566 (19)	0.059 (2)	−0.0135 (14)	0.0077 (15)	−0.0286 (17)
C14	0.0332 (16)	0.0585 (19)	0.067 (2)	−0.0022 (14)	−0.0076 (15)	−0.0275 (18)
C15	0.0414 (17)	0.0416 (15)	0.0527 (18)	0.0004 (13)	−0.0143 (14)	−0.0164 (14)
C16	0.0365 (15)	0.0346 (13)	0.0420 (15)	−0.0074 (11)	−0.0021 (12)	−0.0144 (12)
C17	0.0315 (13)	0.0328 (13)	0.0378 (14)	−0.0079 (10)	−0.0037 (11)	−0.0115 (11)
C18	0.061 (2)	0.0499 (18)	0.0401 (17)	0.0023 (16)	−0.0113 (15)	0.0023 (15)
C19	0.051 (2)	0.070 (2)	0.052 (2)	−0.0303 (17)	0.0147 (16)	−0.0114 (18)
C20	0.117 (5)	0.084 (3)	0.109 (4)	−0.019 (3)	−0.038 (4)	−0.003 (3)
C21	0.099 (4)	0.056 (2)	0.063 (3)	−0.003 (2)	0.019 (2)	−0.010 (2)
C22	0.153 (6)	0.071 (3)	0.081 (3)	−0.034 (3)	0.015 (3)	−0.022 (3)
Cu2	0.03880 (19)	0.03451 (16)	0.02912 (16)	−0.00780 (14)	−0.00024 (14)	−0.00084 (14)
N1	0.0625 (18)	0.0373 (13)	0.0317 (13)	−0.0001 (12)	0.0018 (12)	0.0014 (11)
N2	0.0490 (15)	0.0431 (13)	0.0323 (12)	−0.0213 (11)	0.0042 (11)	−0.0092 (11)
N3	0.0517 (16)	0.0426 (14)	0.0546 (17)	−0.0123 (12)	−0.0041 (13)	−0.0090 (13)
N4	0.0424 (15)	0.0607 (17)	0.0417 (15)	−0.0184 (13)	0.0044 (12)	−0.0147 (13)
N5	0.0500 (17)	0.0454 (15)	0.0623 (18)	−0.0177 (13)	0.0185 (14)	−0.0138 (14)
O1	0.0326 (10)	0.0514 (12)	0.0324 (10)	−0.0059 (9)	−0.0036 (8)	0.0044 (9)
O2	0.0373 (11)	0.0522 (12)	0.0375 (11)	−0.0141 (9)	0.0013 (9)	−0.0015 (9)
O3	0.0360 (11)	0.0396 (10)	0.0342 (10)	−0.0018 (8)	0.0006 (8)	−0.0005 (9)
O4	0.0397 (11)	0.0387 (10)	0.0376 (11)	−0.0001 (8)	−0.0067 (9)	0.0004 (9)
O5	0.0666 (16)	0.0520 (13)	0.0429 (12)	−0.0183 (11)	0.0025 (11)	−0.0113 (11)
O6	0.105 (2)	0.0482 (14)	0.085 (2)	−0.0268 (15)	−0.0138 (18)	−0.0155 (14)
O7	0.0694 (16)	0.0457 (12)	0.0414 (12)	−0.0210 (11)	0.0005 (11)	−0.0025 (10)
O8	0.0641 (15)	0.0494 (12)	0.0365 (11)	−0.0139 (11)	0.0023 (10)	−0.0052 (10)
O9	0.0754 (19)	0.098 (2)	0.0495 (15)	−0.0150 (16)	0.0049 (13)	−0.0367 (16)
O10	0.0538 (14)	0.0500 (13)	0.0507 (14)	−0.0041 (10)	−0.0009 (11)	−0.0126 (11)
O11	0.0489 (14)	0.0500 (13)	0.0649 (16)	−0.0132 (10)	−0.0024 (11)	−0.0077 (12)
O12	0.085 (2)	0.0648 (17)	0.115 (3)	−0.0453 (16)	0.0311 (19)	−0.0355 (18)
O13	0.0676 (17)	0.0407 (12)	0.0568 (15)	−0.0125 (11)	0.0042 (13)	−0.0008 (11)
O14	0.180 (4)	0.069 (2)	0.076 (2)	−0.009 (2)	−0.003 (2)	0.0073 (18)
Sm1	0.03475 (8)	0.03416 (8)	0.02833 (8)	−0.00614 (5)	−0.00093 (5)	0.00000 (5)

Geometric parameters (Å, º) top

C1—O1	1.335 (3)	C18—H15	0.9600
C1—C6	1.381 (4)	C18—H16	0.9600
C1—C2	1.402 (4)	C18—H17	0.9600
C2—C3	1.360 (4)	C19—O2	1.436 (4)
C2—O2	1.382 (4)	C19—H18	0.9600
C3—C4	1.393 (5)	C19—H19	0.9600
C3—H1	0.9300	C19—H20	0.9600
C4—C5	1.353 (5)	C20—C21	1.488 (7)
C4—H2	0.9300	C20—H21	0.9600
C5—C6	1.414 (4)	C20—H22	0.9600
C5—H3	0.9300	C20—H23	0.9600
C6—C7	1.433 (5)	C21—O14	1.186 (5)
C7—N1	1.281 (4)	C21—C22	1.518 (7)
C7—H4	0.9300	C22—H24	0.9600
C8—N1	1.481 (4)	C22—H25	0.9600
C8—C9	1.506 (6)	C22—H26	0.9600
C8—H5	0.9700	Cu2—O3	1.933 (2)
C8—H6	0.9700	Cu2—O1	1.942 (2)
C9—C10	1.479 (5)	Cu2—N2	1.962 (3)
C9—H7	0.9700	Cu2—N1	1.965 (3)
C9—H8	0.9700	N3—O6	1.215 (4)
C10—N2	1.474 (4)	N3—O5	1.249 (4)
C10—H9	0.9700	N3—O7	1.265 (4)
C10—H10	0.9700	N4—O9	1.201 (3)
C11—N2	1.291 (4)	N4—O10	1.254 (3)
C11—C12	1.424 (4)	N4—O8	1.274 (3)
C11—H11	0.9300	N5—O12	1.221 (4)
C12—C17	1.395 (4)	N5—O13	1.238 (4)
C12—C13	1.407 (4)	N5—O11	1.261 (4)
C13—C14	1.359 (5)	O1—Sm1	2.359 (2)
C13—H12	0.9300	O2—Sm1	2.520 (2)
C14—C15	1.393 (5)	O3—Sm1	2.380 (2)
C14—H13	0.9300	O4—Sm1	2.510 (2)
C15—C16	1.386 (4)	O5—Sm1	2.501 (2)
C15—H14	0.9300	O7—Sm1	2.517 (2)
C16—O4	1.381 (4)	O8—Sm1	2.469 (2)
C16—C17	1.394 (4)	O10—Sm1	2.525 (2)
C17—O3	1.326 (3)	O11—Sm1	2.515 (3)
C18—O4	1.443 (4)	O13—Sm1	2.577 (3)

O1—C1—C6	122.4 (3)	H25—C22—H26	109.5
O1—C1—C2	118.8 (3)	O3—Cu2—O1	79.81 (9)
C6—C1—C2	118.7 (3)	O3—Cu2—N2	91.27 (10)
C3—C2—O2	124.3 (3)	O1—Cu2—N2	171.07 (9)
C3—C2—C1	121.9 (3)	O3—Cu2—N1	169.89 (10)
O2—C2—C1	113.8 (2)	O1—Cu2—N1	90.75 (11)
C2—C3—C4	119.1 (3)	N2—Cu2—N1	98.18 (12)
C2—C3—H1	120.4	C7—N1—C8	114.6 (3)
C4—C3—H1	120.4	C7—N1—Cu2	124.2 (2)
C5—C4—C3	120.2 (3)	C8—N1—Cu2	121.2 (2)
C5—C4—H2	119.9	C11—N2—C10	114.6 (3)
C3—C4—H2	119.9	C11—N2—Cu2	124.6 (2)
C4—C5—C6	121.2 (3)	C10—N2—Cu2	120.8 (2)
C4—C5—H3	119.4	O6—N3—O5	121.5 (3)
C6—C5—H3	119.4	O6—N3—O7	122.7 (3)
C1—C6—C5	118.8 (3)	O5—N3—O7	115.9 (3)
C1—C6—C7	122.5 (3)	O9—N4—O10	122.3 (3)
C5—C6—C7	118.6 (3)	O9—N4—O8	122.0 (3)
N1—C7—C6	128.8 (3)	O10—N4—O8	115.7 (2)
N1—C7—H4	115.6	O12—N5—O13	121.7 (3)
C6—C7—H4	115.6	O12—N5—O11	122.0 (3)
N1—C8—C9	112.9 (3)	O13—N5—O11	116.3 (3)
N1—C8—H5	109.0	C1—O1—Cu2	128.75 (18)
C9—C8—H5	109.0	C1—O1—Sm1	123.53 (18)
N1—C8—H6	109.0	Cu2—O1—Sm1	107.68 (9)
C9—C8—H6	109.0	C2—O2—C19	117.3 (2)
H5—C8—H6	107.8	C2—O2—Sm1	118.50 (17)
C10—C9—C8	112.1 (3)	C19—O2—Sm1	123.5 (2)
C10—C9—H7	109.2	C17—O3—Cu2	129.08 (18)
C8—C9—H7	109.2	C17—O3—Sm1	123.76 (17)
C10—C9—H8	109.2	Cu2—O3—Sm1	107.15 (9)
C8—C9—H8	109.2	C16—O4—C18	117.2 (2)
H7—C9—H8	107.9	C16—O4—Sm1	118.80 (16)
N2—C10—C9	112.3 (3)	C18—O4—Sm1	121.66 (19)
N2—C10—H9	109.2	N3—O5—Sm1	97.49 (18)
C9—C10—H9	109.2	N3—O7—Sm1	96.27 (18)
N2—C10—H10	109.2	N4—O8—Sm1	97.71 (17)
C9—C10—H10	109.2	N4—O10—Sm1	95.60 (17)
H9—C10—H10	107.9	N5—O11—Sm1	98.4 (2)
N2—C11—C12	128.3 (3)	N5—O13—Sm1	96.02 (18)
N2—C11—H11	115.9	O1—Sm1—O3	63.27 (8)
C12—C11—H11	115.9	O1—Sm1—O8	148.32 (8)
C17—C12—C13	119.5 (3)	O3—Sm1—O8	146.44 (8)
C17—C12—C11	122.5 (3)	O1—Sm1—O5	73.64 (8)
C13—C12—C11	117.8 (3)	O3—Sm1—O5	73.43 (8)
C14—C13—C12	121.1 (3)	O8—Sm1—O5	117.84 (8)
C14—C13—H12	119.5	O1—Sm1—O4	124.51 (7)
C12—C13—H12	119.5	O3—Sm1—O4	64.03 (7)
C13—C14—C15	119.9 (3)	O8—Sm1—O4	87.13 (8)
C13—C14—H13	120.0	O5—Sm1—O4	76.07 (8)
C15—C14—H13	120.0	O1—Sm1—O11	115.72 (8)
C16—C15—C14	119.6 (3)	O3—Sm1—O11	80.42 (8)
C16—C15—H14	120.2	O8—Sm1—O11	73.58 (9)
C14—C15—H14	120.2	O5—Sm1—O11	144.02 (8)
O4—C16—C15	124.5 (3)	O4—Sm1—O11	70.38 (8)
O4—C16—C17	114.3 (2)	O1—Sm1—O7	117.15 (8)
C15—C16—C17	121.2 (3)	O3—Sm1—O7	114.49 (8)
O3—C17—C16	118.4 (3)	O8—Sm1—O7	67.60 (8)
O3—C17—C12	123.0 (3)	O5—Sm1—O7	50.26 (8)
C16—C17—C12	118.6 (3)	O4—Sm1—O7	71.58 (8)
O4—C18—H15	109.5	O11—Sm1—O7	125.99 (8)
O4—C18—H16	109.5	O1—Sm1—O2	64.43 (7)
H15—C18—H16	109.5	O3—Sm1—O2	123.87 (7)
O4—C18—H17	109.5	O8—Sm1—O2	89.45 (8)
H15—C18—H17	109.5	O5—Sm1—O2	73.80 (8)
H16—C18—H17	109.5	O4—Sm1—O2	143.74 (7)
O2—C19—H18	109.5	O11—Sm1—O2	142.17 (8)
O2—C19—H19	109.5	O7—Sm1—O2	73.77 (8)
H18—C19—H19	109.5	O1—Sm1—O10	100.83 (8)
O2—C19—H20	109.5	O3—Sm1—O10	139.45 (8)
H18—C19—H20	109.5	O8—Sm1—O10	50.74 (8)
H19—C19—H20	109.5	O5—Sm1—O10	141.10 (8)
C21—C20—H21	109.5	O4—Sm1—O10	130.89 (7)
C21—C20—H22	109.5	O11—Sm1—O10	73.75 (9)
H21—C20—H22	109.5	O7—Sm1—O10	105.97 (8)
C21—C20—H23	109.5	O2—Sm1—O10	69.44 (8)
H21—C20—H23	109.5	O1—Sm1—O13	69.00 (8)
H22—C20—H23	109.5	O3—Sm1—O13	71.58 (8)
O14—C21—C20	122.5 (5)	O8—Sm1—O13	104.97 (8)
O14—C21—C22	121.5 (5)	O5—Sm1—O13	137.17 (8)
C20—C21—C22	115.9 (4)	O4—Sm1—O13	108.91 (9)
C21—C22—H24	109.5	O11—Sm1—O13	49.23 (8)
C21—C22—H25	109.5	O7—Sm1—O13	172.57 (8)
H24—C22—H25	109.5	O2—Sm1—O13	106.84 (8)
C21—C22—H26	109.5	O10—Sm1—O13	67.87 (9)
H24—C22—H26	109.5

Experimental details

Crystal data
Chemical formula	[CuSm(C₁₉H₂₀N₂O₄)(NO₃)₃]·C₃H₆O
M_r	798.37
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.384 (5), 12.111 (5), 13.529 (6)
α, β, γ (°)	73.071 (18), 86.984 (19), 72.346 (18)
V (Å³)	1400.5 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.33 × 0.30 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.446, 0.610
No. of measured, independent and observed [I > 2σ(I)] reflections	13938, 6381, 5692
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.062, 1.09
No. of reflections	6381
No. of parameters	392
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.41

Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Acknowledgements

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (Nos. 20572018 and 20672032), Heilongjiang Province (Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang 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 Corporation (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. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar

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