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

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ISSN: 2056-9890

Bis(μ-2-phen­­oxy­propionato-κ2O:O′)bis­­[(1,10-phenanthroline-κ2N,N′)bis­­(2-phen­­oxy­propionato-κ2O,O′)samarium(III)]

aCollege of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and bZhejiang Normal University Xingzhi College, Jinhua, Zhejiang 321004, People's Republic of China
*Correspondence e-mail: sky53@zjnu.cn

(Received 19 August 2011; accepted 25 August 2011; online 31 August 2011)

The dimeric title compound, [Sm2(C9H9O3)6(C12H8N2)2], is centrosymmetric and is composed of six 2-phen­oxy­propionate anions and two 1,10-phenanthroline ligands. The SmIII atom is coordinated by two O atoms from two bridging anions, four O atoms from two chelating anions and the N atoms of the N-heterocycle in a distorted dodeca­hedral geometry.

Related literature

For the biological activity of phen­oxy­alkanoic acids, see: Markus & Buser (1997[Markus, D. M. & Buser, H. R. (1997). Environ. Sci. Technol. 31, 1953-1959.]). For bond lengths and angles in related structures, see: Ye et al. (2010[Ye, H.-M., Ren, N., Zhang, J.-J., Sun, S.-J. & Wang, J.-F. (2010). New J. Chem. 34, 533-540.]).

[Scheme 1]

Experimental

Crystal data
  • [Sm2(C9H9O3)6(C12H8N2)2]

  • Mr = 1652.08

  • Triclinic, [P \overline 1]

  • a = 11.3589 (6) Å

  • b = 12.2144 (6) Å

  • c = 14.1282 (8) Å

  • α = 99.111 (3)°

  • β = 91.116 (3)°

  • γ = 114.381 (3)°

  • V = 1754.98 (16) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.73 mm−1

  • T = 296 K

  • 0.40 × 0.29 × 0.05 mm

Data collection
  • Bruker APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.556, Tmax = 0.919

  • 23059 measured reflections

  • 6164 independent reflections

  • 5585 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.079

  • S = 1.08

  • 6164 reflections

  • 460 parameters

  • 18 restraints

  • H-atom parameters constrained

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.70 e Å−3

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The group of phenoxyalkanoic acids includes a considerable number of important herbicides. The desired biological activity is largely dependent on the length of the carbon chain of the alkanoic acid, the nature of the phenoxy group, and the position of its attachment to the carbon chain (Markus et al., 1997). The structures of 2-phenoxypropionic acid complexes coupled with their special functionality are our interests. Here, we describe a new SmIII complex.

The dimeric title compound [Sm2(C9H9O3)6(C12H8N2)2] (Scheme I) is centrosymmetric and it comprises of six 2-phenoxypropionate anions and two 1,10-phenanthroline ligands. The SmIII atoms are bridged by two anions. The SmIII atom coordinated by two O atoms from two bridging anions, four O atoms from two chelating anions and the N atoms of the N-heterocycle in a dodecahedronal geometry (Fig. 1).

The Sm—Sm separation is 5.1452 (3) Å.

The analysis of structural features indicates that the Sm ion adopts a distorted dodecahedron geometry (Fig. 2) (Ye et al., 2010). Such a geometry is seldom reported and is interesting in lanthanide carboxylate complexes. The L ligands are coordinated to the SmIII ions in two different modes: chelating and bridging. The Sm—O distances are all within the range 2.199 (3)–2.396 (3) Å, and the Sm—N distances range from 2.459 (3)–2.480 (3) Å, all of which are within the range of those of other eight-coordinated SmIII complexes with carboxylic donor ligands and 1,10-phenanthroline (Ye et al., 2010). The most significant intermolecular interactions are C—H···O hydrogen bonds(Table 2) and weak π···π aromatic interactions from the phenananthroline molecules and aromatic rings of the anionic ligands.

Related literature top

For the biological activity of phenoxyalkanoic acids, see: Markus & Buser (1997). For bond lengths and angles in related structures, see: Ye et al. (2010);.

Experimental top

Reagents and solvents used were of commercially available quality. 2-Phenoxypropionic acid (1.5 mmol), Sm(NO3)3.6H2O (0.5 mmol) and 1,10-phenanthroline (0.5 mmol) were dissolved in 20 ml e nthanol; 10 ml water was added to the solution. The solution was stirred for 12 h at room temperature. Colorless crystals were obtained after several days.

Refinement top

The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [aliphatic C—H =0.96 Å (Uiso(H) = 1.5Ueq(C)), aromatic C—H = 0.93 Å (Uiso(H) = 1.2Ueq(C))].

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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
[Figure 1] Fig. 1. The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The coordination environment of the Sm(III).
Bis(µ-2-phenoxypropionato-κ2O:O')bis[(1,10-phenanthroline- κ2N,N')bis(2-phenoxypropionato- κ2O,O')samarium(III)] top
Crystal data top
[Sm2(C9H9O3)6(C12H8N2)2]Z = 1
Mr = 1652.08F(000) = 834
Triclinic, P1Dx = 1.563 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.3589 (6) ÅCell parameters from 9923 reflections
b = 12.2144 (6) Åθ = 1.9–25.0°
c = 14.1282 (8) ŵ = 1.73 mm1
α = 99.111 (3)°T = 296 K
β = 91.116 (3)°Block, colourless
γ = 114.381 (3)°0.40 × 0.29 × 0.05 mm
V = 1754.98 (16) Å3
Data collection top
Bruker APEXII area-detector
diffractometer
6164 independent reflections
Radiation source: fine-focus sealed tube5585 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.556, Tmax = 0.919k = 1414
23059 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0504P)2 + 0.4271P]
where P = (Fo2 + 2Fc2)/3
6164 reflections(Δ/σ)max = 0.002
460 parametersΔρmax = 0.65 e Å3
18 restraintsΔρmin = 0.70 e Å3
Crystal data top
[Sm2(C9H9O3)6(C12H8N2)2]γ = 114.381 (3)°
Mr = 1652.08V = 1754.98 (16) Å3
Triclinic, P1Z = 1
a = 11.3589 (6) ÅMo Kα radiation
b = 12.2144 (6) ŵ = 1.73 mm1
c = 14.1282 (8) ÅT = 296 K
α = 99.111 (3)°0.40 × 0.29 × 0.05 mm
β = 91.116 (3)°
Data collection top
Bruker APEXII area-detector
diffractometer
6164 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5585 reflections with I > 2σ(I)
Tmin = 0.556, Tmax = 0.919Rint = 0.028
23059 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02918 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 1.08Δρmax = 0.65 e Å3
6164 reflectionsΔρmin = 0.70 e Å3
460 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
xyzUiso*/Ueq
Sm10.821883 (15)0.887562 (13)0.604388 (11)0.03012 (8)
C190.9324 (4)0.8368 (3)0.3955 (3)0.0417 (9)
O90.7694 (3)0.6931 (3)0.2678 (2)0.0622 (8)
N20.6794 (3)0.9250 (3)0.4929 (2)0.0459 (8)
O21.0181 (3)0.8723 (2)0.6407 (2)0.0521 (7)
O10.8364 (3)0.7135 (2)0.6450 (2)0.0582 (7)
O81.0419 (3)0.9270 (2)0.4104 (2)0.0568 (7)
N10.5970 (3)0.7250 (3)0.5784 (3)0.0507 (8)
O30.9648 (3)0.6020 (3)0.7353 (2)0.0625 (8)
C10.9580 (4)0.7664 (3)0.6573 (3)0.0444 (8)
O60.6034 (3)0.9804 (3)0.8792 (2)0.0716 (9)
C370.5571 (4)0.8368 (4)0.4654 (3)0.0470 (9)
C200.9041 (4)0.7522 (4)0.2987 (3)0.0506 (10)
H20A0.95170.79810.25030.061*
O50.8677 (3)0.9529 (3)0.7753 (2)0.0679 (9)
O70.8510 (3)0.8087 (3)0.4545 (2)0.0557 (7)
O40.7112 (3)0.9757 (3)0.7047 (2)0.0663 (8)
C100.7742 (4)0.9820 (4)0.7803 (3)0.0492 (8)
C21.0366 (4)0.7021 (4)0.6887 (3)0.0534 (10)
H2A1.11220.76120.73200.064*
C110.7397 (4)1.0285 (4)0.8767 (3)0.0573 (11)
H11A0.77801.00480.92820.069*
C380.5137 (4)0.7313 (4)0.5106 (3)0.0492 (10)
C220.7137 (4)0.7577 (4)0.2246 (3)0.0554 (11)
C390.3889 (4)0.6380 (4)0.4844 (3)0.0594 (11)
C350.5525 (5)0.6292 (4)0.6230 (3)0.0589 (11)
H35A0.60780.62490.67020.071*
C300.5161 (5)0.9533 (5)0.3591 (3)0.0643 (12)
H30A0.46200.96390.31470.077*
C280.7173 (4)1.0236 (4)0.4537 (3)0.0553 (10)
H28A0.80091.08410.47180.066*
C130.5368 (5)0.8547 (4)0.8707 (3)0.0605 (11)
C330.3482 (5)0.5388 (4)0.5327 (4)0.0666 (13)
H33A0.26600.47500.51670.080*
C360.4727 (4)0.8471 (4)0.3979 (3)0.0561 (11)
C31.0824 (6)0.6470 (5)0.6017 (4)0.0744 (14)
H3A1.13280.60690.62220.112*
H3B1.13480.71050.56850.112*
H3C1.00860.58860.55930.112*
C290.6393 (5)1.0424 (5)0.3868 (4)0.0681 (13)
H29A0.67011.11380.36140.082*
C340.4293 (5)0.5363 (4)0.6030 (4)0.0653 (12)
H34A0.40220.47250.63740.078*
C40.9277 (5)0.6275 (4)0.8253 (3)0.0579 (11)
C230.7806 (5)0.8736 (4)0.2077 (4)0.0692 (13)
H23A0.86810.91730.22940.083*
C90.9416 (6)0.7410 (5)0.8705 (4)0.0743 (14)
H9A0.98000.80880.84130.089*
C120.7871 (6)1.1663 (4)0.8946 (4)0.0785 (15)
H12A0.76441.19310.95630.118*
H12B0.74711.18900.84530.118*
H12C0.87971.20400.89350.118*
C210.9466 (6)0.6517 (5)0.3091 (4)0.0810 (16)
H21A0.92960.59750.24830.122*
H21B0.89930.60680.35630.122*
H21C1.03790.68740.32920.122*
C180.5918 (6)0.7774 (5)0.8792 (4)0.0735 (14)
H18A0.68170.80660.88830.088*
C320.3066 (5)0.6504 (5)0.4112 (4)0.0773 (15)
H32A0.22430.58800.39180.093*
C310.3475 (5)0.7507 (5)0.3710 (4)0.0744 (14)
H31A0.29260.75700.32460.089*
C270.5839 (5)0.6938 (5)0.1956 (4)0.0761 (14)
H27A0.53790.61610.20930.091*
C170.5140 (7)0.6548 (6)0.8743 (4)0.0881 (17)
H17A0.55210.60200.88210.106*
C250.5894 (7)0.8629 (6)0.1260 (4)0.0911 (18)
H25A0.54790.89780.09150.109*
C240.7171 (7)0.9254 (6)0.1581 (4)0.0879 (18)
H24A0.76261.00430.14640.105*
C50.8736 (7)0.5269 (6)0.8683 (5)0.099 (2)
H5A0.86490.45090.83620.118*
C160.3792 (7)0.6083 (5)0.8578 (4)0.0905 (18)
H16A0.32670.52550.85390.109*
C80.8972 (6)0.7520 (6)0.9608 (4)0.0894 (17)
H8A0.90420.82760.99240.107*
C140.4038 (6)0.8110 (5)0.8534 (4)0.0838 (16)
H14A0.36680.86460.84570.101*
C260.5222 (6)0.7471 (6)0.1455 (4)0.0929 (19)
H26A0.43440.70420.12480.112*
C150.3266 (6)0.6900 (6)0.8476 (5)0.0959 (19)
H15A0.23710.66180.83660.115*
C60.8321 (9)0.5382 (7)0.9594 (5)0.126 (3)
H6A0.79790.47090.98970.151*
C70.8421 (7)0.6498 (7)1.0040 (5)0.113 (2)
H7A0.81160.65751.06420.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sm10.02637 (11)0.03024 (10)0.03149 (12)0.00984 (8)0.00305 (7)0.00517 (7)
C190.041 (2)0.0375 (18)0.048 (2)0.0173 (17)0.0013 (18)0.0091 (16)
O90.0541 (19)0.0538 (16)0.066 (2)0.0129 (14)0.0041 (15)0.0035 (14)
N20.0414 (19)0.0523 (18)0.0432 (19)0.0195 (15)0.0042 (14)0.0075 (14)
O20.0368 (12)0.0486 (15)0.074 (2)0.0189 (12)0.0051 (13)0.0172 (13)
O10.0499 (18)0.0466 (14)0.080 (2)0.0178 (13)0.0007 (15)0.0243 (13)
O80.0521 (18)0.0442 (15)0.0641 (19)0.0106 (14)0.0015 (14)0.0101 (13)
N10.0422 (19)0.0498 (18)0.058 (2)0.0162 (15)0.0107 (16)0.0113 (16)
O30.075 (2)0.0549 (16)0.066 (2)0.0332 (16)0.0171 (16)0.0196 (14)
C10.040 (2)0.045 (2)0.052 (2)0.0203 (16)0.0015 (17)0.0091 (16)
O60.066 (2)0.070 (2)0.083 (2)0.0318 (17)0.0235 (18)0.0153 (17)
C370.039 (2)0.059 (2)0.042 (2)0.0212 (19)0.0057 (17)0.0032 (18)
C200.044 (2)0.050 (2)0.052 (2)0.0164 (19)0.0068 (19)0.0039 (18)
O50.079 (2)0.103 (2)0.0377 (10)0.058 (2)0.0036 (14)0.0052 (14)
O70.0533 (18)0.0556 (16)0.0523 (18)0.0178 (14)0.0152 (15)0.0069 (13)
O40.0654 (11)0.0731 (11)0.0633 (11)0.0335 (9)0.0019 (8)0.0092 (9)
C100.055 (2)0.051 (2)0.0451 (13)0.0270 (19)0.0130 (14)0.0042 (16)
C20.048 (2)0.050 (2)0.064 (3)0.0214 (19)0.006 (2)0.0150 (19)
C110.058 (3)0.065 (3)0.050 (3)0.029 (2)0.007 (2)0.006 (2)
C380.040 (2)0.056 (2)0.048 (2)0.0190 (19)0.0083 (18)0.0011 (18)
C220.059 (3)0.056 (2)0.048 (2)0.027 (2)0.001 (2)0.0026 (19)
C390.041 (2)0.062 (3)0.062 (3)0.013 (2)0.007 (2)0.000 (2)
C350.055 (3)0.057 (2)0.063 (3)0.019 (2)0.016 (2)0.016 (2)
C300.055 (3)0.092 (3)0.056 (3)0.041 (3)0.004 (2)0.015 (2)
C280.052 (3)0.059 (2)0.057 (3)0.023 (2)0.005 (2)0.018 (2)
C130.063 (3)0.057 (3)0.060 (3)0.023 (2)0.020 (2)0.009 (2)
C330.048 (3)0.058 (3)0.080 (4)0.010 (2)0.015 (2)0.005 (2)
C360.044 (2)0.074 (3)0.051 (3)0.027 (2)0.0055 (19)0.007 (2)
C30.086 (4)0.072 (3)0.085 (4)0.047 (3)0.036 (3)0.025 (3)
C290.066 (3)0.080 (3)0.069 (3)0.036 (3)0.008 (3)0.026 (3)
C340.057 (3)0.053 (2)0.078 (3)0.014 (2)0.020 (3)0.014 (2)
C40.060 (3)0.069 (3)0.052 (3)0.032 (2)0.010 (2)0.016 (2)
C230.071 (3)0.064 (3)0.069 (3)0.029 (3)0.006 (3)0.003 (2)
C90.092 (4)0.082 (3)0.062 (3)0.049 (3)0.007 (3)0.014 (3)
C120.086 (4)0.064 (3)0.074 (4)0.028 (3)0.008 (3)0.008 (2)
C210.083 (4)0.065 (3)0.102 (4)0.044 (3)0.011 (3)0.003 (3)
C180.075 (3)0.070 (3)0.078 (4)0.032 (3)0.011 (3)0.015 (3)
C320.042 (3)0.090 (4)0.080 (4)0.013 (3)0.002 (2)0.003 (3)
C310.049 (3)0.105 (4)0.064 (3)0.028 (3)0.007 (2)0.014 (3)
C270.060 (3)0.077 (3)0.080 (4)0.026 (3)0.002 (3)0.004 (3)
C170.107 (5)0.083 (4)0.085 (4)0.049 (4)0.007 (4)0.022 (3)
C250.111 (5)0.097 (4)0.079 (4)0.066 (4)0.009 (4)0.006 (3)
C240.104 (5)0.079 (4)0.087 (4)0.048 (4)0.010 (4)0.006 (3)
C50.123 (5)0.082 (4)0.085 (4)0.032 (4)0.036 (4)0.028 (3)
C160.095 (5)0.072 (3)0.090 (4)0.018 (3)0.033 (3)0.018 (3)
C80.101 (5)0.109 (5)0.069 (4)0.059 (4)0.007 (3)0.004 (3)
C140.078 (4)0.080 (4)0.096 (4)0.036 (3)0.013 (3)0.016 (3)
C260.078 (4)0.116 (5)0.086 (4)0.055 (4)0.015 (3)0.015 (4)
C150.075 (4)0.093 (4)0.107 (5)0.022 (3)0.020 (3)0.017 (4)
C60.169 (8)0.105 (5)0.090 (5)0.036 (5)0.063 (5)0.032 (4)
C70.124 (6)0.134 (6)0.071 (4)0.042 (5)0.035 (4)0.019 (4)
Geometric parameters (Å, º) top
Sm1—O8i2.199 (3)C28—H28A0.9300
Sm1—O72.272 (3)C13—C181.347 (7)
Sm1—O42.335 (3)C13—C141.380 (7)
Sm1—O12.356 (3)C33—C341.355 (7)
Sm1—O22.366 (3)C33—H33A0.9300
Sm1—O52.396 (3)C36—C311.417 (7)
Sm1—N22.459 (3)C3—H3A0.9600
Sm1—N12.480 (3)C3—H3B0.9600
Sm1—C12.708 (4)C3—H3C0.9600
Sm1—C102.731 (4)C29—H29A0.9300
C19—O71.237 (5)C34—H34A0.9300
C19—O81.261 (5)C4—C91.374 (6)
C19—C201.517 (5)C4—C51.373 (7)
O9—C221.395 (5)C23—C241.382 (7)
O9—C201.420 (5)C23—H23A0.9300
N2—C281.318 (5)C9—C81.389 (7)
N2—C371.361 (5)C9—H9A0.9300
O2—C11.251 (5)C12—H12A0.9600
O1—C11.255 (5)C12—H12B0.9600
O8—Sm1i2.199 (3)C12—H12C0.9600
N1—C351.333 (5)C21—H21A0.9600
N1—C381.366 (5)C21—H21B0.9600
O3—C41.376 (5)C21—H21C0.9600
O3—C21.430 (5)C18—C171.379 (8)
C1—C21.512 (5)C18—H18A0.9300
O6—C131.387 (5)C32—C311.342 (8)
O6—C111.415 (5)C32—H32A0.9300
C37—C361.396 (6)C31—H31A0.9300
C37—C381.436 (6)C27—C261.384 (8)
C20—C211.517 (6)C27—H27A0.9300
C20—H20A0.9800C17—C161.396 (9)
O5—C101.252 (5)C17—H17A0.9300
O4—C101.247 (5)C25—C241.357 (8)
C10—C111.513 (6)C25—C261.378 (9)
C2—C31.512 (6)C25—H25A0.9300
C2—H2A0.9800C24—H24A0.9300
C11—C121.516 (6)C5—C61.385 (9)
C11—H11A0.9800C5—H5A0.9300
C38—C391.400 (6)C16—C151.381 (8)
C22—C231.365 (7)C16—H16A0.9300
C22—C271.370 (6)C8—C71.390 (9)
C39—C331.400 (7)C8—H8A0.9300
C39—C321.447 (7)C14—C151.359 (8)
C35—C341.377 (6)C14—H14A0.9300
C35—H35A0.9300C26—H26A0.9300
C30—C291.372 (7)C15—H15A0.9300
C30—C361.390 (7)C6—C71.365 (9)
C30—H30A0.9300C6—H6A0.9300
C28—C291.391 (6)C7—H7A0.9300
O8i—Sm1—O791.47 (11)C27—C22—O9114.6 (4)
O8i—Sm1—O488.17 (12)C33—C39—C38118.1 (4)
O7—Sm1—O4149.77 (12)C33—C39—C32123.1 (4)
O8i—Sm1—O1136.67 (11)C38—C39—C32118.7 (4)
O7—Sm1—O183.32 (11)N1—C35—C34123.8 (5)
O4—Sm1—O1116.71 (11)N1—C35—H35A118.1
O8i—Sm1—O281.62 (10)C34—C35—H35A118.1
O7—Sm1—O280.95 (11)C29—C30—C36119.6 (4)
O4—Sm1—O2128.74 (11)C29—C30—H30A120.2
O1—Sm1—O255.06 (10)C36—C30—H30A120.2
O8i—Sm1—O587.81 (12)N2—C28—C29123.8 (4)
O7—Sm1—O5155.91 (12)N2—C28—H28A118.1
O4—Sm1—O554.29 (11)C29—C28—H28A118.1
O1—Sm1—O580.78 (11)C18—C13—C14120.3 (5)
O2—Sm1—O575.13 (10)C18—C13—O6125.2 (5)
O8i—Sm1—N282.55 (11)C14—C13—O6114.4 (4)
O7—Sm1—N274.33 (11)C34—C33—C39119.6 (4)
O4—Sm1—N275.66 (11)C34—C33—H33A120.2
O1—Sm1—N2135.64 (10)C39—C33—H33A120.2
O2—Sm1—N2150.16 (11)C30—C36—C37117.8 (4)
O5—Sm1—N2129.29 (10)C30—C36—C31122.4 (4)
O8i—Sm1—N1148.53 (12)C37—C36—C31119.7 (4)
O7—Sm1—N187.20 (11)C2—C3—H3A109.5
O4—Sm1—N177.76 (11)C2—C3—H3B109.5
O1—Sm1—N174.40 (11)H3A—C3—H3B109.5
O2—Sm1—N1128.97 (10)C2—C3—H3C109.5
O5—Sm1—N1105.65 (12)H3A—C3—H3C109.5
N2—Sm1—N166.81 (11)H3B—C3—H3C109.5
O8i—Sm1—C1109.08 (11)C30—C29—C28118.6 (5)
O7—Sm1—C182.08 (12)C30—C29—H29A120.7
O4—Sm1—C1126.40 (12)C28—C29—H29A120.7
O1—Sm1—C127.59 (10)C33—C34—C35119.2 (5)
O2—Sm1—C127.50 (10)C33—C34—H34A120.4
O5—Sm1—C175.45 (11)C35—C34—H34A120.4
N2—Sm1—C1154.05 (11)C9—C4—C5121.4 (5)
N1—Sm1—C1101.87 (11)C9—C4—O3125.2 (4)
O8i—Sm1—C1089.10 (12)C5—C4—O3113.4 (4)
O7—Sm1—C10176.79 (12)C22—C23—C24119.4 (5)
O4—Sm1—C1027.08 (11)C22—C23—H23A120.3
O1—Sm1—C1098.42 (12)C24—C23—H23A120.3
O2—Sm1—C10102.26 (12)C4—C9—C8118.5 (5)
O5—Sm1—C1027.27 (11)C4—C9—H9A120.7
N2—Sm1—C10102.62 (12)C8—C9—H9A120.7
N1—Sm1—C1090.66 (12)C11—C12—H12A109.5
C1—Sm1—C10100.72 (12)C11—C12—H12B109.5
O7—C19—O8125.5 (4)H12A—C12—H12B109.5
O7—C19—C20118.2 (3)C11—C12—H12C109.5
O8—C19—C20116.2 (4)H12A—C12—H12C109.5
C22—O9—C20118.2 (3)H12B—C12—H12C109.5
C28—N2—C37117.5 (4)C20—C21—H21A109.5
C28—N2—Sm1123.5 (3)C20—C21—H21B109.5
C37—N2—Sm1118.9 (3)H21A—C21—H21B109.5
C1—O2—Sm191.7 (2)C20—C21—H21C109.5
C1—O1—Sm192.0 (2)H21A—C21—H21C109.5
C19—O8—Sm1i152.9 (3)H21B—C21—H21C109.5
C35—N1—C38117.4 (4)C13—C18—C17119.6 (6)
C35—N1—Sm1124.9 (3)C13—C18—H18A120.2
C38—N1—Sm1117.6 (3)C17—C18—H18A120.2
C4—O3—C2118.2 (3)C31—C32—C39120.8 (5)
O2—C1—O1121.1 (3)C31—C32—H32A119.6
O2—C1—C2118.0 (3)C39—C32—H32A119.6
O1—C1—C2120.8 (3)C32—C31—C36121.3 (5)
O2—C1—Sm160.83 (19)C32—C31—H31A119.3
O1—C1—Sm160.40 (19)C36—C31—H31A119.3
C2—C1—Sm1178.4 (3)C22—C27—C26118.8 (6)
C13—O6—C11117.2 (4)C22—C27—H27A120.6
N2—C37—C36122.7 (4)C26—C27—H27A120.6
N2—C37—C38117.7 (4)C18—C17—C16121.2 (6)
C36—C37—C38119.6 (4)C18—C17—H17A119.4
O9—C20—C21106.4 (4)C16—C17—H17A119.4
O9—C20—C19112.2 (3)C24—C25—C26119.0 (6)
C21—C20—C19108.5 (4)C24—C25—H25A120.5
O9—C20—H20A109.9C26—C25—H25A120.5
C21—C20—H20A109.9C25—C24—C23121.0 (6)
C19—C20—H20A109.9C25—C24—H24A119.5
C10—O5—Sm191.5 (2)C23—C24—H24A119.5
C19—O7—Sm1138.2 (3)C4—C5—C6120.1 (6)
C10—O4—Sm194.4 (3)C4—C5—H5A119.9
O4—C10—O5119.5 (4)C6—C5—H5A119.9
O4—C10—C11119.8 (4)C15—C16—C17117.5 (6)
O5—C10—C11120.6 (4)C15—C16—H16A121.3
O4—C10—Sm158.5 (2)C17—C16—H16A121.3
O5—C10—Sm161.3 (2)C9—C8—C7119.9 (6)
C11—C10—Sm1176.6 (3)C9—C8—H8A120.1
O3—C2—C1113.8 (3)C7—C8—H8A120.1
O3—C2—C3105.3 (3)C15—C14—C13120.4 (6)
C1—C2—C3109.8 (4)C15—C14—H14A119.8
O3—C2—H2A109.3C13—C14—H14A119.8
C1—C2—H2A109.3C25—C26—C27120.9 (6)
C3—C2—H2A109.3C25—C26—H26A119.6
O6—C11—C10110.6 (4)C27—C26—H26A119.6
O6—C11—C12105.8 (4)C14—C15—C16121.0 (6)
C10—C11—C12111.4 (4)C14—C15—H15A119.5
O6—C11—H11A109.6C16—C15—H15A119.5
C10—C11—H11A109.6C7—C6—C5119.0 (7)
C12—C11—H11A109.6C7—C6—H6A120.5
N1—C38—C39121.8 (4)C5—C6—H6A120.5
N1—C38—C37118.4 (3)C6—C7—C8121.0 (6)
C39—C38—C37119.8 (4)C6—C7—H7A119.5
C23—C22—C27120.9 (5)C8—C7—H7A119.5
C23—C22—O9124.5 (4)
O8i—Sm1—N2—C285.0 (3)O8i—Sm1—O4—C1091.6 (3)
O7—Sm1—N2—C2888.7 (3)O7—Sm1—O4—C10178.6 (2)
O4—Sm1—N2—C2895.0 (3)O1—Sm1—O4—C1051.4 (3)
O1—Sm1—N2—C28151.3 (3)O2—Sm1—O4—C1013.9 (3)
O2—Sm1—N2—C2853.5 (4)O5—Sm1—O4—C103.0 (2)
O5—Sm1—N2—C2886.0 (3)N2—Sm1—O4—C10174.4 (3)
N1—Sm1—N2—C28177.6 (3)N1—Sm1—O4—C10116.8 (3)
C1—Sm1—N2—C28114.0 (4)C1—Sm1—O4—C1020.9 (3)
C10—Sm1—N2—C2892.4 (3)Sm1—O4—C10—O55.3 (4)
O8i—Sm1—N2—C37178.9 (3)Sm1—O4—C10—C11176.6 (3)
O7—Sm1—N2—C3787.4 (3)Sm1—O5—C10—O45.2 (4)
O4—Sm1—N2—C3788.9 (3)Sm1—O5—C10—C11176.8 (4)
O1—Sm1—N2—C3724.8 (3)O8i—Sm1—C10—O487.8 (3)
O2—Sm1—N2—C37122.6 (3)O1—Sm1—C10—O4135.1 (3)
O5—Sm1—N2—C3797.9 (3)O2—Sm1—C10—O4169.0 (2)
N1—Sm1—N2—C376.3 (3)O5—Sm1—C10—O4174.7 (4)
C1—Sm1—N2—C3762.1 (4)N2—Sm1—C10—O45.6 (3)
C10—Sm1—N2—C3791.5 (3)N1—Sm1—C10—O460.8 (3)
O8i—Sm1—O2—C1176.9 (2)C1—Sm1—C10—O4163.0 (3)
O7—Sm1—O2—C190.2 (2)O8i—Sm1—C10—O587.0 (3)
O4—Sm1—O2—C196.1 (3)O4—Sm1—C10—O5174.7 (4)
O1—Sm1—O2—C12.1 (2)O1—Sm1—C10—O550.2 (3)
O5—Sm1—O2—C187.0 (2)O2—Sm1—C10—O55.8 (3)
N2—Sm1—O2—C1124.4 (3)N2—Sm1—C10—O5169.1 (3)
N1—Sm1—O2—C111.3 (3)N1—Sm1—C10—O5124.5 (3)
C10—Sm1—O2—C189.7 (2)C1—Sm1—C10—O522.3 (3)
O8i—Sm1—O1—C10.6 (3)C4—O3—C2—C169.5 (5)
O7—Sm1—O1—C185.7 (3)C4—O3—C2—C3170.2 (4)
O4—Sm1—O1—C1118.1 (2)O2—C1—C2—O3160.7 (4)
O2—Sm1—O1—C12.1 (2)O1—C1—C2—O321.7 (6)
O5—Sm1—O1—C176.2 (3)O2—C1—C2—C381.6 (5)
N2—Sm1—O1—C1145.1 (2)O1—C1—C2—C396.0 (5)
N1—Sm1—O1—C1174.6 (3)C13—O6—C11—C1063.1 (5)
C10—Sm1—O1—C197.0 (3)C13—O6—C11—C12176.1 (4)
O7—C19—O8—Sm1i103.3 (7)O4—C10—C11—O641.7 (6)
C20—C19—O8—Sm1i81.0 (7)O5—C10—C11—O6140.3 (4)
O8i—Sm1—N1—C35162.4 (3)O4—C10—C11—C1275.8 (5)
O7—Sm1—N1—C35109.3 (3)O5—C10—C11—C12102.3 (5)
O4—Sm1—N1—C3597.1 (3)C35—N1—C38—C393.6 (6)
O1—Sm1—N1—C3525.5 (3)Sm1—N1—C38—C39173.9 (3)
O2—Sm1—N1—C3533.3 (4)C35—N1—C38—C37176.7 (4)
O5—Sm1—N1—C3550.0 (3)Sm1—N1—C38—C375.8 (5)
N2—Sm1—N1—C35176.5 (4)N2—C37—C38—N10.0 (5)
C1—Sm1—N1—C3528.0 (3)C36—C37—C38—N1178.2 (4)
C10—Sm1—N1—C3573.1 (3)N2—C37—C38—C39179.7 (4)
O8i—Sm1—N1—C3820.3 (4)C36—C37—C38—C392.1 (6)
O7—Sm1—N1—C3868.0 (3)C20—O9—C22—C231.6 (6)
O4—Sm1—N1—C3885.6 (3)C20—O9—C22—C27179.1 (4)
O1—Sm1—N1—C38151.8 (3)N1—C38—C39—C332.8 (6)
O2—Sm1—N1—C38144.0 (3)C37—C38—C39—C33177.5 (4)
O5—Sm1—N1—C38132.7 (3)N1—C38—C39—C32179.3 (4)
N2—Sm1—N1—C386.2 (3)C37—C38—C39—C320.4 (6)
C1—Sm1—N1—C38149.3 (3)C38—N1—C35—C341.4 (6)
C10—Sm1—N1—C38109.6 (3)Sm1—N1—C35—C34175.9 (3)
Sm1—O2—C1—O13.7 (4)C37—N2—C28—C290.4 (6)
Sm1—O2—C1—C2178.7 (3)Sm1—N2—C28—C29176.5 (3)
Sm1—O1—C1—O23.8 (4)C11—O6—C13—C1813.9 (7)
Sm1—O1—C1—C2178.8 (3)C11—O6—C13—C14167.1 (4)
O8i—Sm1—C1—O23.2 (3)C38—C39—C33—C340.4 (7)
O7—Sm1—C1—O285.6 (2)C32—C39—C33—C34177.4 (5)
O4—Sm1—C1—O2105.5 (2)C29—C30—C36—C371.1 (7)
O1—Sm1—C1—O2176.3 (4)C29—C30—C36—C31178.8 (5)
O5—Sm1—C1—O285.7 (2)N2—C37—C36—C301.2 (6)
N2—Sm1—C1—O2110.2 (3)C38—C37—C36—C30177.0 (4)
N1—Sm1—C1—O2171.0 (2)N2—C37—C36—C31178.7 (4)
C10—Sm1—C1—O296.0 (2)C38—C37—C36—C313.2 (6)
O8i—Sm1—C1—O1179.5 (2)C36—C30—C29—C280.3 (7)
O7—Sm1—C1—O190.7 (2)N2—C28—C29—C300.5 (7)
O4—Sm1—C1—O178.2 (3)C39—C33—C34—C352.6 (7)
O2—Sm1—C1—O1176.3 (4)N1—C35—C34—C331.7 (7)
O5—Sm1—C1—O198.0 (3)C2—O3—C4—C97.5 (7)
N2—Sm1—C1—O166.1 (4)C2—O3—C4—C5172.4 (5)
N1—Sm1—C1—O15.3 (3)C27—C22—C23—C242.0 (8)
C10—Sm1—C1—O187.7 (3)O9—C22—C23—C24175.4 (5)
C28—N2—C37—C360.5 (6)C5—C4—C9—C81.3 (8)
Sm1—N2—C37—C36175.9 (3)O3—C4—C9—C8178.8 (5)
C28—N2—C37—C38177.7 (4)C14—C13—C18—C172.5 (8)
Sm1—N2—C37—C386.0 (4)O6—C13—C18—C17176.5 (5)
C22—O9—C20—C21160.5 (4)C33—C39—C32—C31176.0 (5)
C22—O9—C20—C1981.0 (4)C38—C39—C32—C311.8 (8)
O7—C19—C20—O932.5 (5)C39—C32—C31—C360.7 (9)
O8—C19—C20—O9151.6 (3)C30—C36—C31—C32178.3 (5)
O7—C19—C20—C2184.8 (5)C37—C36—C31—C321.8 (8)
O8—C19—C20—C2191.2 (4)C23—C22—C27—C262.4 (8)
O8i—Sm1—O5—C1092.3 (3)O9—C22—C27—C26175.3 (4)
O7—Sm1—O5—C10179.0 (2)C13—C18—C17—C161.9 (9)
O4—Sm1—O5—C102.9 (2)C26—C25—C24—C231.4 (9)
O1—Sm1—O5—C10129.7 (3)C22—C23—C24—C250.1 (9)
O2—Sm1—O5—C10174.2 (3)C9—C4—C5—C60.2 (10)
N2—Sm1—O5—C1013.7 (3)O3—C4—C5—C6179.6 (7)
N1—Sm1—O5—C1058.9 (3)C18—C17—C16—C150.6 (9)
C1—Sm1—O5—C10157.4 (3)C4—C9—C8—C71.1 (9)
O8—C19—O7—Sm17.0 (7)C18—C13—C14—C151.9 (9)
C20—C19—O7—Sm1177.4 (3)O6—C13—C14—C15177.2 (5)
O8i—Sm1—O7—C1921.0 (4)C24—C25—C26—C271.1 (9)
O4—Sm1—O7—C19109.9 (4)C22—C27—C26—C250.8 (9)
O1—Sm1—O7—C19115.8 (4)C13—C14—C15—C160.6 (10)
O2—Sm1—O7—C1960.3 (4)C17—C16—C15—C140.0 (10)
O5—Sm1—O7—C1966.9 (5)C4—C5—C6—C72.0 (13)
N2—Sm1—O7—C19102.9 (4)C5—C6—C7—C82.3 (13)
N1—Sm1—O7—C19169.5 (4)C9—C8—C7—C60.7 (12)
C1—Sm1—O7—C1988.1 (4)
Symmetry code: (i) x+2, y+2, z+1.

Experimental details

Crystal data
Chemical formula[Sm2(C9H9O3)6(C12H8N2)2]
Mr1652.08
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)11.3589 (6), 12.2144 (6), 14.1282 (8)
α, β, γ (°)99.111 (3), 91.116 (3), 114.381 (3)
V3)1754.98 (16)
Z1
Radiation typeMo Kα
µ (mm1)1.73
Crystal size (mm)0.40 × 0.29 × 0.05
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.556, 0.919
No. of measured, independent and
observed [I > 2σ(I)] reflections
23059, 6164, 5585
Rint0.028
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.079, 1.08
No. of reflections6164
No. of parameters460
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.65, 0.70

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

References

First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMarkus, D. M. & Buser, H. R. (1997). Environ. Sci. Technol. 31, 1953–1959.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYe, H.-M., Ren, N., Zhang, J.-J., Sun, S.-J. & Wang, J.-F. (2010). New J. Chem. 34, 533–540.  Google Scholar

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