Bis(μ-2-{bis­[(2-oxidobenzyl­idene)amino]­meth­yl}phenolato)bis­[(tetra­hydro­furan)­samarium(III)] tetra­hydro­furan disolvate

Li, L.; Zhou, Y.; Yuan, F.

doi:10.1107/S1600536812015759

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m603-m604

doi:10.1107/S1600536812015759

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Bis(μ-2-{bis[(2-oxidobenzylidene)amino]methyl}phenolato)bis[(tetrahydrofuran)samarium(III)] tetrahydrofuran disolvate

Li Li,^a Yuan Zhou ^a and Fugen Yuan ^a ^*

^aSchool of Chemistry and Biochemistry, University of Science and Technology of Suzhou, Suzhou 215009, People's Republic of China
^*Correspondence e-mail: yuanfugensuzhou@163.com

(Received 22 March 2012; accepted 11 April 2012; online 18 April 2012)

In the centrosymmetric binuclear complex of the title solvate, [Sm₂(C₂₁H₁₅N₂O₃)₂(C₄H₈O)₂]·2C₄H₈O, the Sm^III is coordinated in a distorted monocapped octahedral geometry by four O atoms and two N atoms from two tridentate deprotonated 2-{bis[(2-oxidobenzylidene)amino]methyl}phenolate ligands and an O atom of a tetrahydrofuran (THF) molecule. The Sm⋯Sm distance in the complex is 3.8057 (4) Å. Parts of the coordinating THF molecule are disordered over two sets of sites in a 0.56 (3):0.44 (3) ratio. The complex and solvent molecules are linked into a three-dimensional structure via C—H⋯O hydrogen-bonding interactions.

Related literature

For general reports on the tripodal ligand 2-bis-(salicylidieneamino)methylphenol, see: Nabulsi et al. (1988 ); Achim et al. (2001 ); Yu et al. (1991 ); Snyder et al.(1989 ); Chaudhuri et al. (1998 ); Illingsworth et al. (2002 ). For related structures, see: Howell et al. (1998 ); Liu et al. (1998 ); Dubé et al. (1998 ). For ionic radii, see: Shannon (1976 ).

Experimental

Crystal data

[Sm₂(C₂₁H₁₅N₂O₃)₂(C₄H₈O)₂]·2C₄H₈O
M_r = 1275.84
Monoclinic, P 2₁ /c
a = 11.7184 (11) Å
b = 21.378 (2) Å
c = 11.1464 (11) Å
β = 99.058 (1)°
V = 2757.5 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.17 mm⁻¹
T = 293 K
0.23 × 0.18 × 0.16 mm

Data collection

Rigaku Rapid I CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.635, T_max = 0.723
23697 measured reflections
6291 independent reflections
5362 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.084
S = 1.01
6291 reflections
353 parameters
42 restraints
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O5	0.93	2.56	3.450 (7)	159
C21—H21A⋯O5ⁱ	0.93	2.56	3.424 (6)	155
C22—H22B⋯O3ⁱⁱ	0.97	2.50	3.079 (6)	118
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z.

Data collection: CrystalClear (Rigaku, 2004 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812015759/wm2610sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015759/wm2610Isup2.hkl

checkCIF report

Comment top

Since the tripodal schiff base 2-bis-(salicylidiene-amino)-methyl-phenol (salmp) has been characterized by Nabulsi (1988), it has been used as a chelating ligand for numerous transition metals, including Fe^II, Fe^III, Mn^II, Mn^III, Ti^III, V^III, Cr^III, Co^III and Zr^IV (Achim et al., 2001; Yu et al., 1991; Snyder et al., 1989; Chaudhuri et al.,1998; Illingsworth et al., 2002). However, its coordination behaviour with respect to lanthanide elements has not yet reported to the best of our knowledge. Herein we reported a new dinuclear compound [Sm₂(C₂₁H₁₅N₂O₃)₂(C₄H₈O)₂]^.2(C₄H₈O), (I).

The molecular structure of compound (I) is presented in Fig. 1. The Sm—O bond lengths of 2. 213 (2) Å to the terminal aryloxide and of 2.369 (2) Å to the bridging aryloxide are similar compared to those in the analogous complex [{Sm(api)}₂] (H₃api = 2-(2-hydroxyphenyl)-1,3-bis[4-(2-hydroxyphenyl)-3-azabut-3-enyl]-1,3-imidazoline) (2.282 (4) and 2.388 (3) Å, respectively) (Howell et al., 1998) when the difference of the ionic radii is taken into account. In the title compound, Sm has a coordination number of seven resulting in a distorted mono-capped octahedral coordination geometry for the metal (Fig. 2), whereas in the other structure the coordination number is eight. The radii of seven and eight-coordinate Sm^III are 1.160 and 1.219 Å (Shannon, 1976), respectively. The bond lengths of Sm—N (2.616 (2) to 2.623 (2) Å) are consistent with those in [(η⁵-(C₅H₅)Sm(µ-OC₂₀H₂₀N₂O)]₂.(µ-THF)^.2THF (2.55 (5) to 2.67 (7) Å) (Liu et al., 1998). The Sm···Sm distance in (I) is 3.8057 (4) Å, which is a little shorter than that in [(3,5-Bu^t₄salophen)Sm(OH)]₄^.4toluene (3.9023 (8) Å) (Dubé et al., 1998). Two Sm atoms are bridged by aryloxide groups forming a Sm₂(µ-O)₂ planar rhomb with an acute angles O(1)—Sm(1)—O(1 A) of 73.11 (8)° and an obtuse angle Sm(1)—O(1)—Sm(1 A) of 106.89 (8)°.

The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1, Fig. 3), including an intra-molecular hydrogen bond (C22—H22B···O3 ) and inter-molecular hydrogen bonds (C4—H4A···O5 and C21—H21A···O5).

Related literature top

For general reports on the tripodal ligand 2-bis-(salicylidieneamino)methylphenol, see: Nabulsi et al. (1988); Achim et al. (2001); Yu et al. (1991); Snyder et al.(1989); Chaudhuri et al. (1998); Illingsworth et al. (2002). For related structures, see: Howell et al. (1998); Liu et al. (1998); Dubé et al. (1998). For ionic radii, see: Shannon (1976).

Experimental top

2-bis-(salicylidiene-amino)-methyl-phenol was prepared according to the literature procedure (Illingsworth et al., 2002). To a suspension of SmCl₃ (0.536 g, 2.09 mmol) in 20 ml THF was added a THF solution of Ph₂NK (10.3 ml, 6.27 mmol). The mixture was stirred for 1 d at room temperature. After centrifugation, a clear solution of Sm(NPh₂)₃ was obtained. To this solution was added the tripodal Schiff base (0.724 g, 2.09 mmol) and then stirred for another day. The resulting solution was concentrated and added with a proper volume of 1,2-dimethyloxyethane. Yellow crystals of [Sm₂(C₂₅H₂₃N₂O₄)].2(C₄H₈O) were produced in a yield of ca 50%. m.p. > 250°C, IR(KBr, cm^-1) 3391(w), 3043(w), 2974(w), 2866(w), 1610(s), 1541(s), 1468(s), 1445(s), 1406(s), 1316(s), 1267(m), 1189(w), 1148(m), 1123(w), 1026(w), 1011(m), 968(w), 914(w), 887(m), 852(w), 822(w), 749(s), 691(m), 578(w), 560(w), 452(w).

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL(Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids scaled to 30% probability. H atoms and two uncoordinated THF molecules were omitted. The disorder of one of the THF molecules is not shown. [Symmetry code A: -x+1, -y, -z.]
	Fig. 2. View of the distorted monocapped octahedral coordination geometry of Sm^III with displacement ellipsoids scaled to 30% probability. [Symmetry code A: -x +1, -y, -z.]
	Fig. 3. Packing diagram of the title compound viewed along [100]. Dashed lines indicate hydrogen bonds. The disorder is not shown.

Bis(µ-2-{bis[(2- oxidobenzylidene)amino]methyl}phenolato)bis[(tetrahydrofuran)samarium(III)] tetrahydrofuran disolvate top

Crystal data top

[Sm₂(C₂₁H₁₅N₂O₃)₂(C₄H₈O)₂]·2C₄H₈O	F(000) = 1284
M_r = 1275.84	D_x = 1.537 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6291 reflections
a = 11.7184 (11) Å	θ = 1.8–27.5°
b = 21.378 (2) Å	µ = 2.17 mm⁻¹
c = 11.1464 (11) Å	T = 293 K
β = 99.058 (1)°	Prism, yellow
V = 2757.5 (5) Å³	0.23 × 0.18 × 0.16 mm
Z = 2

Data collection top

Rigaku Rapid I CCD diffractometer	6291 independent reflections
Radiation source: fine-focus sealed tube	5362 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
phi and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −15→15
T_min = 0.635, T_max = 0.723	k = −27→27
23697 measured reflections	l = −14→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0311P)² + 2.4255P] where P = (F_o² + 2F_c²)/3
6291 reflections	(Δ/σ)_max = 0.001
353 parameters	Δρ_max = 0.62 e Å⁻³
42 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Sm₂(C₂₁H₁₅N₂O₃)₂(C₄H₈O)₂]·2C₄H₈O	V = 2757.5 (5) Å³
M_r = 1275.84	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7184 (11) Å	µ = 2.17 mm⁻¹
b = 21.378 (2) Å	T = 293 K
c = 11.1464 (11) Å	0.23 × 0.18 × 0.16 mm
β = 99.058 (1)°

Data collection top

Rigaku Rapid I CCD diffractometer	6291 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	5362 reflections with I > 2σ(I)
T_min = 0.635, T_max = 0.723	R_int = 0.052
23697 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	42 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.01	Δρ_max = 0.62 e Å⁻³
6291 reflections	Δρ_min = −0.49 e Å⁻³
353 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)
Sm1	0.633331 (14)	0.050642 (8)	0.045466 (14)	0.03765 (7)
O1	0.4566 (2)	0.04480 (10)	−0.0885 (2)	0.0399 (5)
N1	0.4689 (2)	0.08291 (12)	0.1669 (2)	0.0368 (6)
C1	0.4042 (3)	0.10064 (16)	−0.1113 (3)	0.0415 (7)
O2	0.7114 (2)	0.05416 (12)	0.2385 (2)	0.0510 (6)
N2	0.2865 (2)	0.03847 (12)	0.0800 (2)	0.0376 (6)
C2	0.4009 (4)	0.1298 (2)	−0.2238 (3)	0.0587 (10)
H2B	0.4309	0.1096	−0.2858	0.070*
O3	0.2239 (2)	−0.08830 (12)	0.0432 (3)	0.0640 (8)
C3	0.3533 (4)	0.1885 (2)	−0.2430 (5)	0.0777 (14)
H3A	0.3516	0.2075	−0.3182	0.093*
C4	0.3082 (4)	0.2194 (2)	−0.1527 (5)	0.0732 (13)
H4A	0.2778	0.2595	−0.1660	0.088*
O5	0.1336 (5)	0.3502 (3)	−0.1746 (6)	0.1290 (16)
C5	0.3088 (3)	0.19034 (17)	−0.0424 (4)	0.0570 (10)
H5A	0.2766	0.2109	0.0178	0.068*
C6	0.3561 (3)	0.13107 (16)	−0.0184 (3)	0.0425 (7)
C7	0.3516 (3)	0.09823 (15)	0.0998 (3)	0.0401 (7)
H7A	0.3123	0.1254	0.1511	0.048*
C8	0.6870 (3)	0.05687 (15)	0.3492 (3)	0.0461 (8)
C9	0.7750 (4)	0.0467 (2)	0.4482 (4)	0.0656 (12)
H9A	0.8493	0.0377	0.4336	0.079*
C10	0.7542 (5)	0.0496 (2)	0.5665 (4)	0.0794 (15)
H10A	0.8145	0.0427	0.6301	0.095*
C11	0.6450 (5)	0.0626 (2)	0.5916 (4)	0.0789 (15)
H11A	0.6309	0.0646	0.6713	0.095*
C12	0.5580 (4)	0.0726 (2)	0.4966 (3)	0.0645 (11)
H12A	0.4843	0.0811	0.5133	0.077*
C13	0.5755 (3)	0.07050 (17)	0.3742 (3)	0.0454 (8)
C14	0.4763 (3)	0.08349 (16)	0.2826 (3)	0.0443 (8)
H14A	0.4087	0.0937	0.3120	0.053*
C15	0.1322 (3)	−0.07402 (19)	0.0914 (3)	0.0505 (8)
C16	0.0517 (4)	−0.1210 (2)	0.1098 (4)	0.0672 (12)
H16A	0.0643	−0.1620	0.0876	0.081*
C17	−0.0452 (4)	−0.1066 (2)	0.1603 (4)	0.0672 (12)
H17A	−0.0966	−0.1383	0.1721	0.081*
C18	−0.0673 (3)	−0.0468 (2)	0.1935 (4)	0.0619 (11)
H18A	−0.1333	−0.0377	0.2269	0.074*
C19	0.0096 (3)	−0.0006 (2)	0.1764 (3)	0.0517 (9)
H19A	−0.0054	0.0402	0.1984	0.062*
C20	0.1104 (3)	−0.01278 (17)	0.1268 (3)	0.0425 (7)
C21	0.1904 (3)	0.03821 (16)	0.1224 (3)	0.0419 (7)
H21A	0.1698	0.0759	0.1546	0.050*
O4	0.6278 (2)	0.17034 (12)	0.0626 (2)	0.0548 (7)
C22	0.6431 (5)	0.2121 (2)	−0.0357 (4)	0.0754 (14)
H22A	0.5697	0.2300	−0.0723	0.091*
H22B	0.6767	0.1902	−0.0978	0.091*
C23	0.7226 (16)	0.2615 (7)	0.0220 (11)	0.079 (4)	0.56 (3)
H23A	0.8018	0.2524	0.0127	0.094*	0.56 (3)
H23B	0.7014	0.3021	−0.0137	0.094*	0.56 (3)
C23'	0.647 (3)	0.2738 (6)	0.0115 (14)	0.088 (6)	0.44 (3)
H23C	0.5731	0.2945	−0.0144	0.106*	0.44 (3)
H23D	0.7064	0.2977	−0.0188	0.106*	0.44 (3)
C24	0.709 (3)	0.2603 (12)	0.146 (2)	0.138 (10)	0.56 (3)
H24A	0.6689	0.2977	0.1659	0.166*	0.56 (3)
H24B	0.7842	0.2595	0.1970	0.166*	0.56 (3)
C24'	0.671 (3)	0.2708 (12)	0.144 (3)	0.102 (8)	0.44 (3)
H24C	0.7510	0.2802	0.1741	0.122*	0.44 (3)
H24D	0.6220	0.2998	0.1803	0.122*	0.44 (3)
C25	0.6426 (6)	0.2047 (2)	0.1716 (5)	0.099 (2)
H25A	0.6848	0.1804	0.2377	0.119*
H25B	0.5685	0.2166	0.1930	0.119*
C26	0.1419 (11)	0.3737 (5)	−0.0552 (11)	0.182 (4)
H26A	0.1247	0.4181	−0.0561	0.219*
H26B	0.2189	0.3671	−0.0104	0.219*
C27	0.0526 (12)	0.3368 (7)	0.0020 (11)	0.210 (5)
H27A	0.0870	0.3019	0.0501	0.252*
H27B	0.0110	0.3632	0.0512	0.252*
C28	−0.0164 (13)	0.3174 (7)	−0.1032 (16)	0.234 (7)
H28A	−0.0423	0.2752	−0.0907	0.281*
H28B	−0.0844	0.3440	−0.1166	0.281*
C29	0.0337 (11)	0.3180 (5)	−0.2067 (13)	0.189 (5)
H29A	0.0490	0.2758	−0.2318	0.227*
H29B	−0.0159	0.3388	−0.2726	0.227*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sm1	0.04306 (11)	0.03983 (11)	0.03134 (10)	0.00188 (7)	0.00982 (7)	−0.00368 (6)
O1	0.0485 (13)	0.0387 (12)	0.0329 (12)	0.0053 (9)	0.0080 (10)	0.0013 (9)
N1	0.0417 (14)	0.0387 (14)	0.0301 (13)	0.0009 (11)	0.0057 (11)	−0.0049 (11)
C1	0.0417 (17)	0.0445 (18)	0.0359 (17)	−0.0001 (14)	−0.0015 (13)	0.0054 (14)
O2	0.0491 (14)	0.0656 (17)	0.0367 (13)	0.0100 (11)	0.0022 (11)	−0.0019 (11)
N2	0.0392 (14)	0.0422 (14)	0.0316 (14)	0.0018 (11)	0.0060 (11)	−0.0041 (11)
C2	0.069 (3)	0.063 (2)	0.042 (2)	0.002 (2)	0.0040 (18)	0.0136 (18)
O3	0.0641 (17)	0.0511 (15)	0.086 (2)	−0.0039 (13)	0.0419 (16)	−0.0080 (14)
C3	0.090 (3)	0.070 (3)	0.068 (3)	0.006 (3)	−0.005 (3)	0.032 (2)
C4	0.075 (3)	0.048 (2)	0.090 (4)	0.010 (2)	−0.005 (3)	0.022 (2)
O5	0.146 (4)	0.104 (3)	0.140 (4)	−0.003 (3)	0.031 (3)	0.027 (3)
C5	0.052 (2)	0.044 (2)	0.074 (3)	0.0074 (17)	0.0041 (19)	−0.0034 (18)
C6	0.0416 (18)	0.0374 (17)	0.0472 (19)	0.0013 (13)	0.0029 (14)	0.0009 (14)
C7	0.0438 (18)	0.0424 (17)	0.0342 (16)	0.0055 (14)	0.0067 (13)	−0.0074 (13)
C8	0.060 (2)	0.0399 (18)	0.0357 (18)	0.0019 (15)	−0.0008 (15)	−0.0005 (13)
C9	0.069 (3)	0.076 (3)	0.047 (2)	0.016 (2)	−0.007 (2)	0.0040 (19)
C10	0.100 (4)	0.092 (4)	0.038 (2)	0.015 (3)	−0.016 (2)	0.008 (2)
C11	0.109 (4)	0.094 (4)	0.031 (2)	0.002 (3)	0.004 (2)	0.007 (2)
C12	0.079 (3)	0.082 (3)	0.034 (2)	−0.002 (2)	0.0131 (19)	0.0017 (19)
C13	0.054 (2)	0.0492 (19)	0.0322 (17)	−0.0051 (16)	0.0049 (15)	0.0009 (14)
C14	0.0471 (19)	0.052 (2)	0.0350 (17)	−0.0029 (15)	0.0118 (14)	−0.0041 (15)
C15	0.048 (2)	0.059 (2)	0.046 (2)	−0.0026 (17)	0.0133 (16)	0.0009 (17)
C16	0.065 (3)	0.059 (2)	0.083 (3)	−0.012 (2)	0.028 (2)	−0.005 (2)
C17	0.047 (2)	0.084 (3)	0.072 (3)	−0.016 (2)	0.015 (2)	0.003 (2)
C18	0.038 (2)	0.098 (3)	0.051 (2)	−0.001 (2)	0.0095 (17)	0.006 (2)
C19	0.0440 (19)	0.071 (2)	0.0399 (19)	0.0075 (17)	0.0066 (15)	0.0024 (17)
C20	0.0377 (17)	0.061 (2)	0.0281 (16)	0.0022 (15)	0.0029 (13)	0.0010 (14)
C21	0.0444 (18)	0.0512 (19)	0.0305 (16)	0.0064 (14)	0.0067 (14)	−0.0026 (13)
O4	0.0740 (18)	0.0430 (14)	0.0503 (15)	−0.0026 (12)	0.0192 (13)	−0.0008 (11)
C22	0.117 (4)	0.054 (2)	0.057 (3)	−0.003 (3)	0.018 (3)	0.013 (2)
C23	0.083 (8)	0.075 (7)	0.081 (7)	−0.023 (6)	0.025 (7)	0.012 (5)
C23'	0.129 (17)	0.041 (6)	0.093 (9)	−0.019 (8)	0.010 (10)	0.004 (6)
C24	0.23 (2)	0.093 (15)	0.078 (11)	−0.082 (15)	−0.006 (13)	−0.015 (9)
C24'	0.20 (2)	0.040 (7)	0.082 (12)	−0.008 (10)	0.077 (14)	−0.004 (7)
C25	0.184 (7)	0.058 (3)	0.062 (3)	−0.022 (3)	0.038 (4)	−0.011 (2)
C26	0.216 (8)	0.150 (7)	0.170 (7)	−0.023 (6)	−0.001 (7)	−0.007 (6)
C27	0.209 (9)	0.256 (9)	0.175 (8)	0.040 (7)	0.066 (7)	0.020 (7)
C28	0.231 (10)	0.228 (10)	0.262 (10)	−0.026 (8)	0.096 (9)	−0.013 (8)
C29	0.175 (10)	0.126 (8)	0.259 (15)	0.000 (7)	0.013 (10)	0.013 (9)

Geometric parameters (Å, º) top

Sm1—O2	2.203 (2)	C15—C20	1.402 (5)
Sm1—O3ⁱ	2.223 (3)	C15—C16	1.414 (5)
Sm1—O1	2.358 (2)	C16—C17	1.380 (6)
Sm1—O1ⁱ	2.380 (2)	C16—H16A	0.9300
Sm1—O4	2.568 (3)	C17—C18	1.365 (6)
Sm1—N1	2.616 (3)	C17—H17A	0.9300
Sm1—N2ⁱ	2.623 (3)	C18—C19	1.371 (6)
Sm1—Sm1ⁱ	3.8057 (4)	C18—H18A	0.9300
O1—C1	1.348 (4)	C19—C20	1.405 (5)
O1—Sm1ⁱ	2.380 (2)	C19—H19A	0.9300
N1—C14	1.279 (4)	C20—C21	1.443 (5)
N1—C7	1.494 (4)	C21—H21A	0.9300
C1—C2	1.396 (5)	O4—C25	1.407 (5)
C1—C6	1.413 (5)	O4—C22	1.446 (5)
O2—C8	1.312 (4)	C22—C23'	1.419 (14)
N2—C21	1.289 (4)	C22—C23	1.486 (12)
N2—C7	1.487 (4)	C22—H22A	0.9700
N2—Sm1ⁱ	2.623 (3)	C22—H22B	0.9700
C2—C3	1.375 (6)	C23—C24	1.42 (3)
C2—H2B	0.9300	C23—H23A	0.9700
O3—C15	1.310 (4)	C23—H23B	0.9700
O3—Sm1ⁱ	2.223 (3)	C23'—C24'	1.46 (3)
C3—C4	1.379 (7)	C23'—H23C	0.9700
C3—H3A	0.9300	C23'—H23D	0.9700
C4—C5	1.376 (6)	C24—C25	1.47 (3)
C4—H4A	0.9300	C24—H24A	0.9700
O5—C29	1.357 (11)	C24—H24B	0.9700
O5—C26	1.412 (11)	C24'—C25	1.49 (3)
C5—C6	1.392 (5)	C24'—H24C	0.9700
C5—H5A	0.9300	C24'—H24D	0.9700
C6—C7	1.501 (5)	C25—H25A	0.9700
C7—H7A	0.9800	C25—H25B	0.9700
C8—C9	1.403 (5)	C26—C27	1.527 (14)
C8—C13	1.409 (5)	C26—H26A	0.9700
C9—C10	1.380 (7)	C26—H26B	0.9700
C9—H9A	0.9300	C27—C28	1.379 (16)
C10—C11	1.381 (8)	C27—H27A	0.9700
C10—H10A	0.9300	C27—H27B	0.9700
C11—C12	1.365 (7)	C28—C29	1.374 (15)
C11—H11A	0.9300	C28—H28A	0.9700
C12—C13	1.412 (5)	C28—H28B	0.9700
C12—H12A	0.9300	C29—H29A	0.9700
C13—C14	1.447 (5)	C29—H29B	0.9700
C14—H14A	0.9300

O2—Sm1—O3ⁱ	101.30 (11)	C18—C17—C16	121.5 (4)
O2—Sm1—O1	143.97 (9)	C18—C17—H17A	119.2
O3ⁱ—Sm1—O1	112.64 (10)	C16—C17—H17A	119.2
O2—Sm1—O1ⁱ	87.80 (9)	C17—C18—C19	118.7 (4)
O3ⁱ—Sm1—O1ⁱ	142.00 (8)	C17—C18—H18A	120.7
O1—Sm1—O1ⁱ	73.11 (8)	C19—C18—H18A	120.7
O2—Sm1—O4	84.53 (9)	C18—C19—C20	122.2 (4)
O3ⁱ—Sm1—O4	72.66 (9)	C18—C19—H19A	118.9
O1—Sm1—O4	94.01 (8)	C20—C19—H19A	118.9
O1ⁱ—Sm1—O4	145.32 (8)	C15—C20—C19	119.0 (3)
O2—Sm1—N1	73.27 (9)	C15—C20—C21	123.2 (3)
O3ⁱ—Sm1—N1	143.28 (9)	C19—C20—C21	117.6 (3)
O1—Sm1—N1	72.33 (8)	N2—C21—C20	128.7 (3)
O1ⁱ—Sm1—N1	74.71 (8)	N2—C21—H21A	115.6
O4—Sm1—N1	70.69 (8)	C20—C21—H21A	115.6
O2—Sm1—N2ⁱ	114.64 (9)	C25—O4—C22	108.6 (3)
O3ⁱ—Sm1—N2ⁱ	70.63 (9)	C25—O4—Sm1	125.7 (3)
O1—Sm1—N2ⁱ	88.65 (8)	C22—O4—Sm1	123.5 (2)
O1ⁱ—Sm1—N2ⁱ	72.04 (8)	C23'—C22—O4	107.1 (7)
O4—Sm1—N2ⁱ	141.16 (8)	O4—C22—C23	104.8 (6)
N1—Sm1—N2ⁱ	145.30 (8)	C23'—C22—H22A	76.2
C1—O1—Sm1	113.65 (19)	O4—C22—H22A	110.8
C1—O1—Sm1ⁱ	126.4 (2)	C23—C22—H22A	110.8
Sm1—O1—Sm1ⁱ	106.89 (8)	C23'—C22—H22B	136.3
C14—N1—C7	114.4 (3)	O4—C22—H22B	110.8
C14—N1—Sm1	125.9 (2)	C23—C22—H22B	110.8
C7—N1—Sm1	119.56 (18)	H22A—C22—H22B	108.9
O1—C1—C2	120.8 (3)	C24—C23—C22	104.4 (11)
O1—C1—C6	119.5 (3)	C24—C23—H23A	110.9
C2—C1—C6	119.7 (3)	C22—C23—H23A	110.9
C8—O2—Sm1	143.3 (2)	C24—C23—H23B	110.9
C21—N2—C7	114.0 (3)	C22—C23—H23B	110.9
C21—N2—Sm1ⁱ	126.8 (2)	H23A—C23—H23B	108.9
C7—N2—Sm1ⁱ	119.02 (18)	C22—C23'—C24'	108.8 (13)
C3—C2—C1	120.0 (4)	C22—C23'—H23C	109.9
C3—C2—H2B	120.0	C24'—C23'—H23C	109.9
C1—C2—H2B	120.0	C22—C23'—H23D	109.9
C15—O3—Sm1ⁱ	145.1 (3)	C24'—C23'—H23D	109.9
C2—C3—C4	121.1 (4)	H23C—C23'—H23D	108.3
C2—C3—H3A	119.4	C23—C24—C25	110.3 (14)
C4—C3—H3A	119.4	C23—C24—H24A	109.6
C5—C4—C3	119.1 (4)	C25—C24—H24A	109.6
C5—C4—H4A	120.5	C23—C24—H24B	109.6
C3—C4—H4A	120.5	C25—C24—H24B	109.6
C29—O5—C26	110.9 (9)	H24A—C24—H24B	108.1
C4—C5—C6	122.0 (4)	C25—C24'—C23'	103.6 (18)
C4—C5—H5A	119.0	C25—C24'—H24C	111.0
C6—C5—H5A	119.0	C23'—C24'—H24C	111.0
C5—C6—C1	118.1 (3)	C25—C24'—H24D	111.0
C5—C6—C7	121.8 (3)	C23'—C24'—H24D	111.0
C1—C6—C7	120.1 (3)	H24C—C24'—H24D	109.0
N2—C7—N1	107.2 (2)	O4—C25—C24'	108.6 (11)
N2—C7—C6	111.1 (3)	O4—C25—C24	104.7 (10)
N1—C7—C6	112.7 (3)	O4—C25—H25A	110.8
N2—C7—H7A	108.6	C24'—C25—H25A	124.0
N1—C7—H7A	108.6	C24—C25—H25A	110.8
C6—C7—H7A	108.6	O4—C25—H25B	110.8
O2—C8—C9	119.4 (4)	C24'—C25—H25B	92.0
O2—C8—C13	122.8 (3)	C24—C25—H25B	110.8
C9—C8—C13	117.8 (4)	H25A—C25—H25B	108.9
C10—C9—C8	121.7 (5)	O5—C26—C27	105.1 (9)
C10—C9—H9A	119.1	O5—C26—H26A	110.7
C8—C9—H9A	119.1	C27—C26—H26A	110.7
C9—C10—C11	120.7 (4)	O5—C26—H26B	110.7
C9—C10—H10A	119.6	C27—C26—H26B	110.7
C11—C10—H10A	119.6	H26A—C26—H26B	108.8
C12—C11—C10	118.5 (4)	C28—C27—C26	98.6 (10)
C12—C11—H11A	120.7	C28—C27—H27A	112.1
C10—C11—H11A	120.7	C26—C27—H27A	112.1
C11—C12—C13	122.7 (4)	C28—C27—H27B	112.1
C11—C12—H12A	118.6	C26—C27—H27B	112.1
C13—C12—H12A	118.6	H27A—C27—H27B	109.7
C8—C13—C12	118.5 (4)	C29—C28—C27	116.1 (14)
C8—C13—C14	124.5 (3)	C29—C28—H28A	108.3
C12—C13—C14	117.0 (4)	C27—C28—H28A	108.3
N1—C14—C13	129.0 (3)	C29—C28—H28B	108.3
N1—C14—H14A	115.5	C27—C28—H28B	108.3
C13—C14—H14A	115.5	H28A—C28—H28B	107.4
O3—C15—C20	122.0 (3)	O5—C29—C28	104.4 (12)
O3—C15—C16	120.2 (4)	O5—C29—H29A	110.9
C20—C15—C16	117.8 (3)	C28—C29—H29A	110.9
C17—C16—C15	120.8 (4)	O5—C29—H29B	110.9
C17—C16—H16A	119.6	C28—C29—H29B	110.9
C15—C16—H16A	119.6	H29A—C29—H29B	108.9

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O5	0.93	2.56	3.450 (7)	159
C21—H21A···O5ⁱⁱ	0.93	2.56	3.424 (6)	155
C22—H22B···O3ⁱ	0.97	2.50	3.079 (6)	118

Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Sm₂(C₂₁H₁₅N₂O₃)₂(C₄H₈O)₂]·2C₄H₈O
M_r	1275.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.7184 (11), 21.378 (2), 11.1464 (11)
β (°)	99.058 (1)
V (Å³)	2757.5 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.17
Crystal size (mm)	0.23 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku Rapid I CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.635, 0.723
No. of measured, independent and observed [I > 2σ(I)] reflections	23697, 6291, 5362
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.084, 1.01
No. of reflections	6291
No. of parameters	353
No. of restraints	42
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.49

Computer programs: CrystalClear (Rigaku, 2004), CrystalStructure (Rigaku/MSC, 2004), SHELXTL (Sheldrick, 2008), SHELXTL(Sheldrick, 2008), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O5	0.93	2.56	3.450 (7)	159.4
C21—H21A···O5ⁱ	0.93	2.56	3.424 (6)	154.8
C22—H22B···O3ⁱⁱ	0.97	2.50	3.079 (6)	118.3

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z.

Acknowledgements

Financial support from the Jiangsu Key Laboratory for Environment Functional Materials and from a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) is gratefully acknowledged.

References

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Volume 68| Part 5| May 2012| Pages m603-m604

doi:10.1107/S1600536812015759

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(μ-2-{bis­­[(2-oxido­benzyl­­idene)amino]­meth­yl}phenolato)bis­­[(tetra­hydro­furan)­samarium(III)] tetra­hydro­furan disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(μ-2-{bis[(2-oxidobenzylidene)amino]methyl}phenolato)bis[(tetrahydrofuran)samarium(III)] tetrahydrofuran disolvate