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Acta Cryst. (2007). E63, m2508-m2509    [ doi:10.1107/S1600536807043528 ]

catena-Poly[[bis([mu]-anilinoacetato-[kappa]2O:O')bis([mu]-anilinoacetato-[kappa]3O,O':O)bis[(1,10-phenanthroline-[kappa]2N,N')samarium(III)]-[mu]-anilinoacetato-[kappa]2O:O']

H. Zhong, X.-M. Yang, H.-L. Xie and C.-J. Luo

Abstract top

In the crystal structure of the title compound, [Sm2(C8H8NO2)6(C12H8N2)2]n, the SmIII atoms are bridged by two terdentate, two bidentate and four mondentate carboxylate groups with an inversion centre between the two SmIII ions. Each Sm atom is nine-coordinated by two N atoms of 1,10-phenanthroline and seven O atoms of four anilinoacetate ligands. In the crystal structure, the chains are linked by hydrogen bonds into a polymeric ribbon structure.

Comment top

In recent years, there has been great interest in the synthesis of metal organic frameworks (MOFs) with organic ligands and rare earth metals because of their novel structures, fascinating properties and important roles in special materials having optical, electronic, magnetic and biological importance potential applications (Daiguebonne et al., 2000; Farrugia et al., 2000; Tsukube & Shinoda, 2002; Zhang et al., 2005). These compounds are usually prepared by the reaction of rare-earth metal ions with bi- or multidentate ligands (Starynowicz, 1991, 1993; Kay et al., 1972; Ma et al., 1999; Zeng et al., 2000; Mao et al., 1998). We report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The title compound, [Sm2(C8H8NO2)6(C12H8N2)2]n, which are the metal organic framework synthesized by the anilinoacetate ligand and the rare earth metal Sm, are bridged by two terdentate, two bidentate and four mondentate carboxyl groups with an inversion centre between the two SmIII ions. Each Sm atom is nine-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and seven O atoms of four anilinoacetate ligands (Table 1). The Sm—O bond lengths are in the range 2.414 (3) to 2.822 (4) Å. The Sm—N bond lengths are in the range 2.710 (4) to 2.728 (4) Å. In the crystal structure, N—H···O, C—H···N and C—H···O hydrogen bonds (Fig. 2 and Table 2) seem to be effective in the stabilization of the structure, resulting in the formation of a supramolecular network structure.

Related literature top

For related literature, see: Allen et al. (1987); Daiguebonne et al. (2000); Farrugia et al. (2000); Kay et al. (1972); Ma et al. (1999); Mao et al. (1998); Starynowicz (1991, 1993); Tsukube & Shinoda (2002); Zhang et al. (2005); Zeng et al. (2000).

Experimental top

Crystals of the title compound (I) were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Samarium (III) nitrate hexahydrate (218.5 mg, 0.5 mmol), phen (198 mg, 1 mmol), anilinoacetic acid (146.2 mg, 1 mmol), ammonia (0.5 mol/l, 2 ml) and distilled water (6 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 423 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colourless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Refinement top

The H atoms were positioned geometrically, with N— H = 0.86 Å (for NH) and C—H = 0.93 - 0.97 Å (for CH), and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C, N), where x = 1.2 for aromatic H atoms and x = 1.5 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top
[Figure 1] Fig. 1. The structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code (A): 2 - x, -y, 2 - z]. All H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
catena-Poly[[bis(µ-anilinoacetato-κ2O:O')bis(µ-\ anilinoacetato-κ3O,O':O)bis[(1,10-phenanthroline-\ κ2N,N')samarium(III)]- bis-(µ-anilinoacetato-κ2O:O')] top
Crystal data top
[Sm2(C8H8NO2)6(C12H8N2)2]F(000) = 1572
Mr = 1562.04Dx = 1.536 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8997 reflections
a = 19.998 (3) Åθ = 2.7–26.7°
b = 8.498 (2) ŵ = 1.79 mm−1
c = 20.783 (2) ÅT = 273 K
β = 106.998 (5)°Plane, colourless
V = 3377.7 (10) Å30.33 × 0.12 × 0.08 mm
Z = 2
Data collection top
Bruker APEX II area-detector
diffractometer		7519 independent reflections
Radiation source: fine-focus sealed tube4974 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 27.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −25→25
Tmin = 0.590, Tmax = 0.871k = −10→11
27195 measured reflectionsl = −26→26
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.1002P)2 + 0.285P]
where P = (Fo2 + 2Fc2)/3
7519 reflections(Δ/σ)max = 0.002
403 parametersΔρmax = 1.54 e Å−3
3 restraintsΔρmin = −0.81 e Å−3
Crystal data top
[Sm2(C8H8NO2)6(C12H8N2)2]V = 3377.7 (10) Å3
Mr = 1562.04Z = 2
Monoclinic, P21/nMo Kα radiation
a = 19.998 (3) ŵ = 1.79 mm−1
b = 8.498 (2) ÅT = 273 K
c = 20.783 (2) Å0.33 × 0.12 × 0.08 mm
β = 106.998 (5)°
Data collection top
Bruker APEX II area-detector
diffractometer		7519 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4974 reflections with I > 2σ(I)
Tmin = 0.590, Tmax = 0.871Rint = 0.043
27195 measured reflectionsθmax = 27.4°
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.152Δρmax = 1.54 e Å−3
S = 0.98Δρmin = −0.81 e Å−3
7519 reflectionsAbsolute structure: ?
403 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
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
Sm10.931196 (13)0.19068 (3)0.964300 (12)0.03994 (12)
O10.84626 (17)−0.0361 (4)0.91902 (17)0.0413 (8)
O20.94708 (19)−0.1388 (5)0.97740 (18)0.0480 (9)
O30.97071 (19)0.0614 (4)0.87480 (17)0.0447 (8)
O41.06691 (19)−0.0829 (4)0.92152 (17)0.0473 (9)
O50.94009 (19)0.4211 (4)1.03423 (17)0.0447 (8)
O61.0073 (2)0.6128 (5)1.09082 (17)0.0531 (10)
N10.7968 (2)0.2338 (6)0.9669 (2)0.0444 (10)
N20.8342 (3)0.3067 (5)0.8547 (2)0.0451 (11)
N31.1177 (2)−0.0164 (5)0.8215 (2)0.0481 (11)
H3A1.1390−0.07460.85510.058*
N40.7857 (2)−0.3269 (5)0.8983 (2)0.0447 (11)
H40.7628−0.34190.85680.054*
N50.9861 (2)0.5266 (5)1.20625 (19)0.0436 (11)
H51.01600.59821.20470.052*
C10.7787 (3)0.1908 (7)1.0198 (3)0.0606 (17)
H10.81370.16761.05920.073*
C20.7093 (4)0.1781 (9)1.0197 (4)0.080 (2)
H20.69810.14871.05840.097*
C30.6582 (4)0.2099 (9)0.9616 (5)0.086 (3)
H30.61150.19890.96030.103*
C40.6742 (4)0.2571 (10)0.9056 (4)0.0717 (19)
C50.7467 (3)0.2673 (7)0.9095 (3)0.0508 (14)
C60.6212 (5)0.2936 (13)0.8394 (6)0.115 (4)
H60.57380.28190.83480.137*
C70.6416 (5)0.3427 (12)0.7869 (5)0.098 (3)
H70.60800.37020.74710.118*
C80.7132 (4)0.3537 (9)0.7906 (3)0.0653 (18)
C90.7671 (3)0.3102 (6)0.8507 (3)0.0499 (14)
C100.7358 (5)0.4034 (9)0.7370 (3)0.086 (2)
H100.70340.43810.69770.103*
C110.8045 (5)0.4019 (9)0.7413 (3)0.078 (2)
H110.81970.43540.70540.094*
C120.8524 (4)0.3491 (7)0.8008 (3)0.0611 (17)
H120.89940.34340.80260.073*
C131.0287 (3)0.0024 (6)0.8770 (2)0.0408 (12)
C141.0520 (3)0.0521 (7)0.8172 (3)0.0525 (14)
H14A1.01780.01880.77600.063*
H14B1.05570.16580.81640.063*
C151.1463 (3)0.0134 (8)0.7697 (3)0.0604 (16)
C161.2074 (4)−0.0576 (10)0.7761 (4)0.074 (2)
H161.2277−0.12030.81340.089*
C171.2401 (4)−0.0366 (11)0.7264 (5)0.090 (2)
H171.2833−0.08320.73080.108*
C181.2091 (6)0.0522 (10)0.6712 (5)0.104 (3)
H181.23110.06340.63760.125*
C191.1481 (6)0.1232 (12)0.6642 (5)0.106 (3)
H191.12750.18360.62630.128*
C201.1148 (4)0.1056 (10)0.7154 (4)0.082 (2)
H201.07250.15550.71220.098*
C210.8834 (3)−0.1514 (7)0.9387 (2)0.0417 (12)
C220.8569 (3)−0.3142 (6)0.9196 (3)0.0534 (15)
H22A0.8754−0.35140.88410.064*
H22B0.8748−0.38260.95820.064*
C230.7543 (7)−0.3144 (10)0.9466 (8)0.1220 (17)
C240.7823 (7)−0.2775 (10)1.0106 (7)0.1220 (17)
H240.8300−0.25751.02670.146*
C250.7405 (6)−0.2680 (12)1.0550 (7)0.1220 (17)
H250.7600−0.24401.10030.146*
C260.6741 (7)−0.2941 (11)1.0303 (7)0.1220 (17)
H260.6472−0.28471.05970.146*
C270.6369 (7)−0.3372 (11)0.9601 (7)0.1220 (17)
H270.5893−0.35910.94480.146*
C280.6792 (6)−0.3411 (12)0.9210 (7)0.1220 (17)
H280.6599−0.36180.87540.146*
C290.9695 (3)0.4988 (6)1.0865 (3)0.0414 (12)
C300.9487 (3)0.4451 (7)1.1472 (3)0.0536 (14)
H30A0.89900.46231.13920.064*
H30B0.95760.33311.15370.064*
C310.9739 (3)0.4896 (7)1.2654 (3)0.0531 (14)
C320.9277 (4)0.3796 (9)1.2718 (3)0.0679 (19)
H320.90150.32441.23420.081*
C330.9192 (6)0.3492 (13)1.3339 (5)0.106 (3)
H330.88830.27131.33850.127*
C340.9573 (5)0.4356 (12)1.3906 (4)0.099 (3)
H340.94970.41991.43220.119*
C351.0045 (4)0.5409 (10)1.3836 (3)0.086 (2)
H351.03120.59541.42120.103*
C361.0143 (4)0.5699 (9)1.3219 (3)0.0692 (18)
H361.04770.64251.31790.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sm10.04626 (18)0.03404 (18)0.03452 (17)−0.00154 (11)0.00400 (11)0.00062 (11)
O10.0414 (18)0.0306 (19)0.045 (2)0.0002 (15)0.0011 (15)−0.0031 (15)
O20.046 (2)0.047 (2)0.043 (2)−0.0021 (18)0.0004 (16)0.0087 (17)
O30.054 (2)0.043 (2)0.0378 (19)0.0038 (18)0.0138 (16)0.0029 (16)
O40.057 (2)0.046 (2)0.040 (2)0.0070 (18)0.0157 (17)0.0103 (17)
O50.063 (2)0.0307 (19)0.0391 (19)−0.0050 (17)0.0125 (16)−0.0051 (15)
O60.077 (3)0.049 (2)0.0344 (19)−0.024 (2)0.0176 (18)−0.0038 (17)
N10.043 (2)0.038 (2)0.045 (3)0.003 (2)0.002 (2)−0.008 (2)
N20.057 (3)0.038 (3)0.032 (2)0.002 (2)−0.0015 (19)0.0013 (18)
N30.048 (2)0.063 (3)0.039 (2)0.018 (2)0.022 (2)0.023 (2)
N40.040 (2)0.032 (3)0.051 (3)−0.0124 (18)−0.003 (2)−0.0068 (19)
N50.063 (3)0.041 (3)0.028 (2)−0.028 (2)0.0153 (19)−0.0057 (17)
C10.052 (3)0.072 (5)0.056 (4)0.007 (3)0.014 (3)−0.004 (3)
C20.057 (4)0.108 (7)0.081 (5)0.001 (4)0.029 (4)−0.014 (4)
C30.046 (4)0.090 (7)0.118 (8)−0.004 (4)0.018 (4)−0.013 (5)
C40.052 (4)0.080 (5)0.070 (5)0.005 (4)−0.002 (3)−0.017 (4)
C50.051 (3)0.033 (3)0.059 (4)0.008 (2)0.001 (3)−0.009 (3)
C60.052 (5)0.152 (11)0.109 (8)0.019 (5)−0.024 (5)−0.037 (7)
C70.080 (6)0.110 (7)0.073 (6)0.037 (5)−0.027 (4)−0.012 (5)
C80.067 (4)0.063 (4)0.045 (4)0.018 (3)−0.016 (3)−0.008 (3)
C90.057 (3)0.032 (3)0.045 (3)0.005 (2)−0.009 (3)−0.004 (2)
C100.119 (7)0.065 (5)0.046 (4)0.015 (5)−0.019 (4)−0.002 (3)
C110.114 (6)0.075 (5)0.034 (3)−0.001 (5)0.003 (4)0.011 (3)
C120.076 (4)0.049 (4)0.048 (4)−0.003 (3)0.003 (3)0.008 (3)
C130.050 (3)0.033 (3)0.038 (3)−0.008 (2)0.010 (2)−0.002 (2)
C140.063 (3)0.053 (4)0.043 (3)0.005 (3)0.019 (3)0.010 (3)
C150.066 (4)0.066 (4)0.055 (4)−0.009 (3)0.027 (3)0.002 (3)
C160.075 (5)0.092 (5)0.067 (4)0.005 (4)0.037 (4)−0.001 (4)
C170.082 (5)0.094 (7)0.109 (7)−0.009 (5)0.053 (5)−0.011 (5)
C180.138 (8)0.077 (6)0.138 (9)−0.014 (6)0.104 (7)−0.002 (6)
C190.153 (9)0.103 (7)0.089 (6)0.015 (7)0.077 (6)0.031 (5)
C200.098 (6)0.087 (6)0.077 (5)0.001 (5)0.053 (4)0.020 (4)
C210.044 (3)0.047 (3)0.029 (2)−0.006 (2)0.004 (2)−0.004 (2)
C220.059 (4)0.045 (4)0.052 (3)0.003 (3)0.010 (3)−0.007 (3)
C230.134 (4)0.086 (3)0.169 (5)0.015 (3)0.079 (4)0.031 (3)
C240.134 (4)0.086 (3)0.169 (5)0.015 (3)0.079 (4)0.031 (3)
C250.134 (4)0.086 (3)0.169 (5)0.015 (3)0.079 (4)0.031 (3)
C260.134 (4)0.086 (3)0.169 (5)0.015 (3)0.079 (4)0.031 (3)
C270.134 (4)0.086 (3)0.169 (5)0.015 (3)0.079 (4)0.031 (3)
C280.134 (4)0.086 (3)0.169 (5)0.015 (3)0.079 (4)0.031 (3)
C290.055 (3)0.030 (3)0.038 (3)−0.001 (2)0.012 (2)0.003 (2)
C300.073 (4)0.049 (3)0.040 (3)−0.021 (3)0.018 (3)−0.005 (2)
C310.072 (4)0.052 (4)0.033 (3)−0.001 (3)0.014 (3)0.003 (2)
C320.071 (4)0.088 (5)0.046 (3)−0.034 (4)0.019 (3)−0.006 (3)
C330.124 (8)0.134 (8)0.075 (6)−0.049 (7)0.053 (6)0.002 (5)
C340.118 (7)0.143 (8)0.044 (4)−0.029 (6)0.034 (4)0.005 (5)
C350.112 (6)0.100 (6)0.040 (4)−0.020 (5)0.013 (4)−0.008 (4)
C360.079 (4)0.073 (5)0.052 (4)−0.018 (4)0.013 (3)−0.012 (3)
Geometric parameters (Å, º) top
Sm1—O12.559 (3)C10—H100.9300
Sm1—O22.822 (4)C11—C121.398 (9)
Sm1—O2i2.421 (4)C11—H110.9300
Sm1—O32.480 (3)C12—H120.9300
Sm1—O4i2.533 (3)C13—C141.509 (7)
Sm1—O52.414 (3)C14—H14A0.9700
Sm1—O6ii2.537 (4)C14—H14B0.9700
Sm1—N12.728 (4)C15—C161.334 (9)
Sm1—N22.710 (4)C15—C201.366 (10)
O1—C211.225 (6)C16—C171.386 (11)
O2—C211.297 (6)C16—H160.9300
O2—Sm1i2.421 (4)C17—C181.363 (13)
O3—C131.252 (6)C17—H170.9300
O4—C131.247 (6)C18—C191.331 (12)
O4—Sm1i2.533 (3)C18—H180.9300
O5—C291.260 (6)C19—C201.419 (10)
O6—C291.215 (6)C19—H190.9300
O6—Sm1ii2.537 (4)C20—H200.9300
N1—C11.307 (8)C21—C221.493 (8)
N1—C51.345 (7)C22—H22A0.9700
N2—C91.321 (8)C22—H22B0.9700
N2—C121.326 (8)C23—C241.320 (17)
N3—C151.383 (7)C23—C281.457 (17)
N3—C141.415 (7)C24—C251.418 (14)
N3—H3A0.8600C24—H240.9300
N4—C231.337 (13)C25—C261.293 (16)
N4—C221.365 (7)C25—H250.9300
N4—H40.8600C26—C271.478 (17)
N5—C311.359 (7)C26—H260.9300
N5—C301.418 (6)C27—C281.332 (14)
N5—H50.8600C27—H270.9300
C1—C21.390 (9)C28—H280.9300
C1—H10.9300C29—C301.511 (7)
C2—C31.363 (12)C30—H30A0.9700
C2—H20.9300C30—H30B0.9700
C3—C41.354 (12)C31—C321.347 (8)
C3—H30.9300C31—C361.395 (8)
C4—C51.431 (9)C32—C331.375 (10)
C4—C61.504 (12)C32—H320.9300
C5—C91.443 (9)C33—C341.407 (12)
C6—C71.338 (14)C33—H330.9300
C6—H60.9300C34—C351.340 (11)
C7—C81.414 (12)C34—H340.9300
C7—H70.9300C35—C361.374 (10)
C8—C101.385 (11)C35—H350.9300
C8—C91.440 (8)C36—H360.9300
C10—C111.350 (11)
O1—Sm1—O248.11 (10)C8—C10—H10119.7
O1—Sm1—O373.35 (12)C10—C11—C12118.9 (7)
O1—Sm1—O5139.14 (12)C10—C11—H11120.5
O2—Sm1—O365.25 (11)C12—C11—H11120.5
O2—Sm1—O5139.49 (11)N2—C12—C11123.2 (7)
O3—Sm1—O5145.83 (12)N2—C12—H12118.4
O1—Sm1—N163.68 (12)C11—C12—H12118.4
O2—Sm1—N1102.42 (13)O4—C13—O3128.3 (5)
O3—Sm1—N1127.29 (13)O4—C13—C14120.2 (5)
O5—Sm1—N177.22 (13)O3—C13—C14111.4 (4)
O1—Sm1—N274.31 (12)N3—C14—C13109.8 (4)
O2—Sm1—N2118.35 (11)N3—C14—H14A109.7
O3—Sm1—N280.65 (13)C13—C14—H14A109.7
O5—Sm1—N296.87 (12)N3—C14—H14B109.7
N1—Sm1—N260.01 (14)C13—C14—H14B109.7
O5—Sm1—O2i87.71 (14)H14A—C14—H14B108.2
O2i—Sm1—O378.49 (12)C16—C15—C20122.1 (6)
O5—Sm1—O4i75.58 (12)C16—C15—N3114.5 (6)
O2i—Sm1—O4i74.21 (12)C20—C15—N3123.4 (6)
O3—Sm1—O4i128.43 (12)C15—C16—C17119.0 (8)
O5—Sm1—O6ii77.15 (12)C15—C16—H16120.5
O2i—Sm1—O6ii78.27 (13)C17—C16—H16120.5
O3—Sm1—O6ii69.53 (12)C18—C17—C16120.2 (8)
O4i—Sm1—O6ii141.66 (12)C18—C17—H17119.9
O2i—Sm1—O1120.60 (13)C16—C17—H17119.9
O4i—Sm1—O184.19 (12)C19—C18—C17121.2 (8)
O6ii—Sm1—O1133.38 (11)C19—C18—H18119.4
O2i—Sm1—N2148.76 (14)C17—C18—H18119.4
O4i—Sm1—N2136.88 (14)C18—C19—C20119.2 (9)
O6ii—Sm1—N272.75 (14)C18—C19—H19120.4
O2i—Sm1—N1150.06 (13)C20—C19—H19120.4
O4i—Sm1—N177.01 (13)C15—C20—C19118.3 (8)
O6ii—Sm1—N1122.05 (14)C15—C20—H20120.8
O2i—Sm1—O272.71 (14)C19—C20—H20120.8
O4i—Sm1—O265.20 (11)O1—C21—O2122.0 (5)
O6ii—Sm1—O2129.87 (12)O1—C21—C22121.3 (5)
C21—O1—Sm1102.0 (3)O2—C21—C22116.7 (5)
C21—O2—Sm1i163.1 (4)N4—C22—C21114.5 (5)
C21—O2—Sm187.7 (3)N4—C22—H22A108.6
Sm1i—O2—Sm1107.29 (14)C21—C22—H22A108.6
C13—O3—Sm1130.2 (3)N4—C22—H22B108.6
C13—O4—Sm1i138.1 (3)C21—C22—H22B108.6
C29—O5—Sm1151.4 (3)H22A—C22—H22B107.6
C29—O6—Sm1ii149.8 (3)C24—C23—N4128.4 (13)
C1—N1—C5119.1 (5)C24—C23—C28119.6 (12)
C1—N1—Sm1119.8 (4)N4—C23—C28112.0 (13)
C5—N1—Sm1119.6 (4)C23—C24—C25120.7 (13)
C9—N2—C12117.8 (5)C23—C24—H24119.6
C9—N2—Sm1121.7 (4)C25—C24—H24119.6
C12—N2—Sm1120.2 (4)C26—C25—C24117.7 (14)
C15—N3—C14117.7 (5)C26—C25—H25121.2
C15—N3—H3A121.2C24—C25—H25121.2
C14—N3—H3A121.2C25—C26—C27126.6 (12)
C23—N4—C22115.1 (8)C25—C26—H26116.7
C23—N4—H4122.4C27—C26—H26116.7
C22—N4—H4122.4C28—C27—C26112.5 (12)
C31—N5—C30118.7 (4)C28—C27—H27123.8
C31—N5—H5120.7C26—C27—H27123.8
C30—N5—H5120.7C27—C28—C23122.9 (14)
N1—C1—C2122.9 (7)C27—C28—H28118.6
N1—C1—H1118.5C23—C28—H28118.6
C2—C1—H1118.5O6—C29—O5127.3 (5)
C3—C2—C1118.4 (7)O6—C29—C30119.7 (5)
C3—C2—H2120.8O5—C29—C30112.8 (5)
C1—C2—H2120.8N5—C30—C29111.7 (4)
C4—C3—C2121.0 (7)N5—C30—H30A109.3
C4—C3—H3119.5C29—C30—H30A109.3
C2—C3—H3119.5N5—C30—H30B109.3
C3—C4—C5117.4 (7)C29—C30—H30B109.3
C3—C4—C6124.6 (8)H30A—C30—H30B107.9
C5—C4—C6118.0 (8)C32—C31—N5124.0 (5)
N1—C5—C4121.2 (6)C32—C31—C36120.2 (6)
N1—C5—C9118.8 (5)N5—C31—C36115.8 (6)
C4—C5—C9120.0 (6)C31—C32—C33119.9 (7)
C7—C6—C4120.6 (8)C31—C32—H32120.1
C7—C6—H6119.7C33—C32—H32120.1
C4—C6—H6119.7C32—C33—C34120.2 (8)
C6—C7—C8121.4 (7)C32—C33—H33119.9
C6—C7—H7119.3C34—C33—H33119.9
C8—C7—H7119.3C35—C34—C33118.9 (7)
C10—C8—C7122.7 (7)C35—C34—H34120.5
C10—C8—C9116.1 (7)C33—C34—H34120.5
C7—C8—C9121.2 (7)C34—C35—C36121.2 (7)
N2—C9—C8123.3 (6)C34—C35—H35119.4
N2—C9—C5118.3 (5)C36—C35—H35119.4
C8—C9—C5118.4 (6)C35—C36—C31119.5 (7)
C11—C10—C8120.5 (6)C35—C36—H36120.3
C11—C10—H10119.7C31—C36—H36120.3
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O60.862.322.658 (5)103
N3—H3A···O40.862.272.628 (5)105
C22—H22B···O5iii0.972.403.345 (7)163
C12—H12···N5ii0.932.603.441 (8)151
C12—H12···O6ii0.932.473.059 (8)121
C10—H10···O1iv0.932.353.218 (7)156
C1—H1···O4i0.932.413.108 (8)132
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+3/2.
Selected geometric parameters (Å, º) top
Sm1—O12.559 (3)Sm1—O52.414 (3)
Sm1—O22.822 (4)Sm1—O6ii2.537 (4)
Sm1—O2i2.421 (4)Sm1—N12.728 (4)
Sm1—O32.480 (3)Sm1—N22.710 (4)
Sm1—O4i2.533 (3)
O1—Sm1—O248.11 (10)O3—Sm1—N1127.29 (13)
O1—Sm1—O373.35 (12)O5—Sm1—N177.22 (13)
O1—Sm1—O5139.14 (12)O1—Sm1—N274.31 (12)
O2—Sm1—O365.25 (11)O2—Sm1—N2118.35 (11)
O2—Sm1—O5139.49 (11)O3—Sm1—N280.65 (13)
O3—Sm1—O5145.83 (12)O5—Sm1—N296.87 (12)
O1—Sm1—N163.68 (12)N1—Sm1—N260.01 (14)
O2—Sm1—N1102.42 (13)
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O60.862.322.658 (5)103
N3—H3A···O40.862.272.628 (5)105
C22—H22B···O5iii0.972.403.345 (7)163
C12—H12···N5ii0.932.603.441 (8)151
C12—H12···O6ii0.932.473.059 (8)121
C10—H10···O1iv0.932.353.218 (7)156
C1—H1···O4i0.932.413.108 (8)132
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+3/2.
Acknowledgements top

We thank the Science and Technology Program of Jinggangshan University for financial support of this work (grant No. 2007).

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Daiguebonne, C., Guillou, O. & Boubekeur, K. (2000). Inorg. Chim. Acta, 304, 161–169.

Farrugia, L. J., Peacock, R. D. & Stewart, B. (2000). Acta Cryst. C56, e435–e436.

Kay, J., Moore, J. W. & Glick, M. D. (1972). Inorg. Chem. 11, 2818–2827.

Ma, L., Evans, O. R., Foxman, B. M. & Lin, W. B. (1999). Inorg. Chem. 38, 5837–5840.

Mao, J. G., Zhang, H. J., Ni, J. Z., Wang, S. B. & Mak, T. C. W. (1998). J. Chem. Crystallogr. 17, 3999–4009.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Siemens (1996). SAINT and SHELXTL. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Starynowicz, P. (1991). Acta Cryst. C47, 294–297.

Starynowicz, P. (1993). Acta Cryst. C49, 1895–1897.

Tsukube, H. & Shinoda, S. (2002). Chem. Rev. 102, 2389–2404.

Zeng, X.-R., Xu, Y., Xiong, R.-G., Zhang, L.-J. & You, X.-Z. (2000). Acta Cryst. C56, e325–e326.

Zhang, Z.-H., Shen, Z.-L., Okamura, T.-A., Zhu, H.-F., Sun, W.-Y. & Ueyama, N. (2005). Cryst. Growth Des. 5, 1191–1197.