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Acta Cryst. (2007). E63, m2592-m2593    [ doi:10.1107/S1600536807045485 ]

catena-Poly[hexakis([mu]2-anilinoacetamide)bis(1,10-phenanthroline)disamarium(III]

T. Liu and J.-Y. Zhu

Abstract top

The molecule of the title compound, [Sm2(C8H9N2O)6(C12H8N2)2]n, is a binuclear polymeric complex and has an inversion centre midway between the two SmIII ions, which are bridged by two tridentate, two bidentate and four mondentate (within the binuclear unit) acetamide groups. Each Sm atom is nine-coordinated by two N atoms of a 1,10-phenanthroline ligand and four O and three N atoms of anilinoacetamide ligands. In the crystal structure, intermolecular C-H...O, C-H...N, N-H...O and N-H...N hydrogen bonds result in the formation of a supramolecular network structure; an intramolecular N-H...O hydrogen bond is also present.

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 (Table 1) are within normal ranges (Allen et al., 1987). It has an inversion centre midway between the two SmIII ions, which are bridged by two terdentate, two bidentate and four monodentate acetamide groups. Each Sm atom is nine-coordinated by two N atoms of a 1,10-phenanthroline (phen) ligand and four O and three N atoms of anilinoacetamide ligands. The Sm—O and Sm—N bonds are in the range of [2.505 (4)–2.561 (4) Å] and [2.404 (4)–2.846 (5) Å], respectively (Table 1).

In the crystal structure, intermolecular C—H···O, C—H···N, N—H···O and N–H···N hydrogen bonds (Table 1, Fig. 2) result in the formation of a supramolecular network structure; intramolecular N—H···O hydrogen bond (Table 1) is also present.

Related literature top

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

Experimental top

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Samarium (III) nitrate hexahydrate (218.5 mg, 0.5 mmol), phen (198 mg, 1 mmol), anilinoacetamide (145.2 mg, 1 mmol) 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 colorless 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

H5 and H8 (for NH) were located in difference syntheses and refined isotropically [N—H = 0.84 (5) and 0.79 (2) Å, Uiso(H) = 0.08 (2) and 0.077 (19) Å2]. The remaining H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 and 0.97 Å, for aromatic and methylene H atoms and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: SMART (Siemens, 1996); 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 molecular 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]. 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[hexakis(µ2-anilinoacetamide)bis(1,10- phenanthroline)disamarium(III] top
Crystal data top
C36H35N8O3SmF(000) = 1572
Mr = 778.08Dx = 1.551 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8983 reflections
a = 19.876 (3) Åθ = 2.6–26.7°
b = 8.5511 (17) ŵ = 1.81 mm−1
c = 20.481 (4) ÅT = 273 K
β = 106.871 (9)°Plate, colourless
V = 3331.2 (11) Å30.33 × 0.12 × 0.08 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		7330 independent reflections
Radiation source: fine-focus sealed tube4913 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 27.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −25→25
Tmin = 0.587, Tmax = 0.870k = −10→11
26612 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.1002P)2 + 0.285P]
where P = (Fo2 + 2Fc2)/3
7330 reflections(Δ/σ)max = 0.001
411 parametersΔρmax = 1.58 e Å−3
7 restraintsΔρmin = −0.90 e Å−3
Crystal data top
C36H35N8O3SmV = 3331.2 (11) Å3
Mr = 778.08Z = 4
Monoclinic, P21/nMo Kα radiation
a = 19.876 (3) ŵ = 1.81 mm−1
b = 8.5511 (17) ÅT = 273 K
c = 20.481 (4) Å0.33 × 0.12 × 0.08 mm
β = 106.871 (9)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		7330 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4913 reflections with I > 2σ(I)
Tmin = 0.587, Tmax = 0.870Rint = 0.042
26612 measured reflectionsθmax = 27.3°
Refinement top
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.160Δρmax = 1.58 e Å−3
S = 1.04Δρmin = −0.90 e Å−3
7330 reflectionsAbsolute structure: ?
411 parametersFlack parameter: ?
7 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
Sm10.931195 (14)0.19069 (3)0.964291 (13)0.03946 (13)
O10.84613 (18)−0.0358 (4)0.91906 (18)0.0411 (8)
O21.0667 (2)−0.0828 (5)0.92142 (18)0.0460 (9)
O31.0067 (2)0.6126 (5)1.09069 (18)0.0526 (11)
N10.7967 (2)0.2337 (6)0.9666 (2)0.0438 (11)
N20.8343 (3)0.3064 (5)0.8548 (2)0.0446 (11)
N31.1178 (2)−0.0165 (6)0.8216 (2)0.0478 (12)
H3A1.1392−0.07480.85550.057*
N40.7856 (2)−0.3269 (5)0.8983 (3)0.0437 (11)
H40.7623−0.34150.85620.052*
N50.9876 (3)0.5266 (6)1.2064 (2)0.0422 (11)
H50.960 (3)0.602 (5)1.205 (2)0.08 (2)*
N70.9710 (2)0.0616 (5)0.87541 (18)0.0295 (8)
H7A0.93970.05610.83630.035*
N80.9399 (2)0.4227 (5)1.03379 (19)0.0300 (8)
H80.938 (3)0.331 (2)1.036 (3)0.077 (19)*
N90.9473 (2)−0.1396 (5)0.9772 (2)0.0321 (9)
H90.9443−0.04810.99350.038*
C10.7786 (4)0.1912 (8)1.0196 (4)0.0610 (18)
H10.81370.16781.05960.073*
C20.7091 (4)0.1790 (10)1.0192 (5)0.079 (2)
H20.69770.14951.05840.095*
C30.6583 (4)0.2104 (10)0.9615 (6)0.087 (3)
H30.61140.19930.96030.104*
C40.6742 (4)0.2576 (11)0.9055 (4)0.072 (2)
C50.7467 (3)0.2676 (7)0.9096 (3)0.0496 (15)
C60.6215 (5)0.2949 (13)0.8391 (6)0.109 (4)
H60.57380.28420.83460.110*
C70.6416 (5)0.3424 (12)0.7873 (5)0.096 (3)
H70.60780.36960.74700.086*
C80.7132 (4)0.3536 (9)0.7907 (3)0.0649 (19)
C90.7667 (3)0.3093 (6)0.8507 (3)0.0497 (15)
C100.7357 (6)0.4045 (10)0.7375 (4)0.086 (3)
H100.70320.44030.69790.083*
C110.8048 (5)0.4033 (10)0.7419 (3)0.078 (2)
H110.81990.43810.70550.083*
C120.8528 (4)0.3503 (8)0.8008 (3)0.0610 (17)
H120.90000.34530.80240.073*
C131.0285 (3)0.0027 (7)0.8772 (3)0.0426 (13)
C141.0522 (3)0.0523 (8)0.8174 (3)0.0514 (15)
H14A1.01780.02040.77540.062*
H14B1.05640.16530.81700.062*
C151.1460 (4)0.0136 (8)0.7692 (3)0.0603 (17)
C161.2072 (4)−0.0568 (10)0.7758 (4)0.073 (2)
H161.2275−0.11990.81340.088*
C171.2396 (5)−0.0342 (11)0.7260 (6)0.089 (3)
H171.2833−0.07930.73040.087*
C181.2085 (6)0.0534 (11)0.6703 (6)0.104 (3)
H181.23040.06430.63610.104*
C191.1479 (6)0.1235 (13)0.6637 (5)0.107 (3)
H191.12730.18430.62550.108*
C201.1144 (5)0.1048 (10)0.7156 (4)0.079 (2)
H201.07200.15400.71270.094*
C210.8831 (3)−0.1522 (7)0.9385 (3)0.0424 (13)
C220.8576 (3)−0.3143 (7)0.9200 (3)0.0527 (15)
H22A0.8764−0.35160.88400.063*
H22B0.8757−0.38150.95930.063*
C230.7552 (8)−0.3148 (11)0.9473 (8)0.1209 (19)
C240.7842 (8)−0.2800 (11)1.0107 (8)0.1209 (19)
H240.8323−0.26171.02670.124*
C250.7417 (7)−0.2701 (12)1.0557 (7)0.1209 (19)
H250.7616−0.24731.10170.071*
C260.6749 (7)−0.2935 (11)1.0311 (8)0.1209 (19)
H260.6478−0.28241.06110.125*
C270.6373 (7)−0.3361 (12)0.9600 (7)0.1209 (19)
H270.5894−0.35710.94480.125*
C280.6791 (7)−0.3412 (12)0.9203 (7)0.1209 (19)
H280.6599−0.36210.87410.105*
C290.9693 (3)0.4999 (7)1.0864 (3)0.0417 (12)
C300.9488 (4)0.4461 (8)1.1474 (3)0.0525 (15)
H30A0.89900.46441.14000.063*
H30B0.95730.33471.15370.063*
C310.9740 (3)0.4892 (8)1.2654 (3)0.0529 (15)
C320.9277 (4)0.3786 (10)1.2720 (3)0.0670 (19)
H320.90210.32271.23400.080*
C330.9188 (6)0.3494 (14)1.3336 (5)0.104 (3)
H330.88760.27211.33840.105*
C340.9568 (5)0.4361 (13)1.3906 (4)0.098 (3)
H340.94910.42081.43280.117*
C351.0044 (5)0.5416 (11)1.3836 (4)0.085 (2)
H351.03100.59591.42170.082*
C361.0144 (4)0.5700 (9)1.3221 (3)0.0682 (19)
H361.04780.64241.31790.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sm10.04558 (19)0.0348 (2)0.03320 (18)−0.00143 (12)0.00387 (12)0.00068 (11)
O10.0412 (19)0.032 (2)0.042 (2)0.0004 (17)0.0003 (16)−0.0024 (16)
O20.056 (2)0.045 (2)0.037 (2)0.0067 (19)0.0140 (17)0.0098 (18)
O30.077 (3)0.049 (3)0.033 (2)−0.024 (2)0.0180 (19)−0.0050 (18)
N10.041 (3)0.041 (3)0.043 (3)0.003 (2)0.002 (2)−0.008 (2)
N20.055 (3)0.040 (3)0.030 (2)0.003 (2)−0.001 (2)0.0008 (19)
N30.048 (3)0.063 (3)0.038 (2)0.016 (2)0.022 (2)0.021 (2)
N40.040 (2)0.033 (3)0.049 (3)−0.0123 (19)−0.002 (2)−0.006 (2)
N50.060 (3)0.041 (3)0.026 (2)−0.020 (3)0.015 (2)−0.0051 (18)
N70.034 (2)0.033 (2)0.0202 (18)0.0040 (18)0.0060 (15)0.0010 (16)
N80.048 (2)0.015 (2)0.026 (2)−0.0049 (18)0.0083 (17)−0.0041 (16)
N90.033 (2)0.026 (2)0.030 (2)−0.0012 (17)−0.0016 (16)0.0041 (16)
C10.054 (4)0.073 (5)0.056 (4)0.007 (3)0.016 (3)−0.001 (3)
C20.055 (4)0.110 (7)0.077 (5)0.004 (4)0.027 (4)−0.010 (5)
C30.045 (4)0.096 (7)0.116 (8)−0.005 (4)0.020 (5)−0.014 (6)
C40.051 (4)0.086 (5)0.067 (5)0.006 (4)−0.002 (4)−0.015 (4)
C50.050 (3)0.034 (3)0.056 (4)0.008 (3)0.002 (3)−0.008 (3)
C60.052 (5)0.140 (11)0.105 (8)0.016 (5)−0.023 (5)−0.036 (7)
C70.081 (6)0.107 (7)0.070 (6)0.037 (5)−0.026 (5)−0.012 (5)
C80.067 (4)0.064 (4)0.042 (4)0.019 (4)−0.017 (3)−0.011 (3)
C90.058 (4)0.032 (3)0.045 (3)0.005 (3)−0.007 (3)−0.004 (2)
C100.121 (7)0.064 (5)0.043 (4)0.016 (5)−0.022 (4)0.000 (3)
C110.112 (7)0.078 (6)0.030 (3)−0.002 (5)0.000 (4)0.013 (3)
C120.076 (5)0.051 (4)0.047 (4)−0.001 (3)0.004 (3)0.009 (3)
C130.059 (3)0.034 (3)0.033 (3)−0.013 (3)0.010 (2)−0.004 (2)
C140.060 (4)0.053 (4)0.043 (3)0.006 (3)0.017 (3)0.010 (3)
C150.066 (4)0.068 (5)0.053 (4)−0.012 (4)0.028 (3)0.001 (3)
C160.072 (5)0.093 (6)0.065 (4)0.006 (4)0.036 (4)−0.001 (4)
C170.081 (6)0.094 (7)0.108 (7)−0.004 (5)0.052 (5)−0.010 (6)
C180.140 (9)0.077 (6)0.135 (9)−0.014 (6)0.104 (8)0.000 (6)
C190.152 (10)0.108 (7)0.086 (7)0.020 (7)0.076 (7)0.034 (6)
C200.093 (6)0.087 (6)0.072 (5)0.002 (5)0.050 (5)0.020 (4)
C210.044 (3)0.050 (4)0.028 (3)−0.005 (3)0.003 (2)−0.005 (2)
C220.058 (4)0.047 (4)0.048 (4)0.001 (3)0.008 (3)−0.007 (3)
C230.133 (4)0.090 (3)0.162 (5)0.016 (3)0.078 (4)0.031 (3)
C240.133 (4)0.090 (3)0.162 (5)0.016 (3)0.078 (4)0.031 (3)
C250.133 (4)0.090 (3)0.162 (5)0.016 (3)0.078 (4)0.031 (3)
C260.133 (4)0.090 (3)0.162 (5)0.016 (3)0.078 (4)0.031 (3)
C270.133 (4)0.090 (3)0.162 (5)0.016 (3)0.078 (4)0.031 (3)
C280.133 (4)0.090 (3)0.162 (5)0.016 (3)0.078 (4)0.031 (3)
C290.054 (3)0.031 (3)0.039 (3)−0.001 (3)0.013 (2)0.005 (2)
C300.071 (4)0.050 (4)0.037 (3)−0.021 (3)0.016 (3)−0.005 (3)
C310.071 (4)0.054 (4)0.032 (3)−0.004 (3)0.013 (3)0.003 (3)
C320.068 (4)0.089 (5)0.044 (4)−0.032 (4)0.017 (3)−0.005 (3)
C330.119 (8)0.136 (8)0.071 (6)−0.045 (7)0.049 (6)0.004 (6)
C340.114 (7)0.141 (9)0.045 (4)−0.028 (7)0.033 (4)0.005 (5)
C350.111 (6)0.098 (6)0.041 (4)−0.019 (5)0.013 (4)−0.009 (4)
C360.079 (5)0.075 (5)0.047 (4)−0.018 (4)0.012 (3)−0.012 (3)
Geometric parameters (Å, º) top
Sm1—O12.561 (4)C8—C91.424 (8)
Sm1—O2i2.505 (4)C10—C111.350 (12)
Sm1—O3ii2.535 (4)C10—H100.9300
Sm1—N12.713 (5)C11—C121.380 (9)
Sm1—N22.685 (5)C11—H110.9300
Sm1—N72.448 (4)C12—H120.9300
Sm1—N82.418 (4)C13—C141.494 (8)
Sm1—N9i2.404 (4)C14—H14A0.9700
Sm1—N92.846 (5)C14—H14B0.9700
O1—C211.233 (7)C15—C161.328 (10)
O2—C131.238 (6)C15—C201.343 (10)
O2—Sm1i2.505 (4)C16—C171.370 (11)
O3—C291.205 (7)C16—H160.9300
O3—Sm1ii2.535 (4)C17—C181.355 (13)
N1—C11.291 (8)C17—H170.9300
N1—C51.327 (7)C18—C191.317 (13)
N2—C121.318 (8)C18—H180.9300
N2—C91.321 (8)C19—C201.417 (10)
N3—C151.373 (7)C19—H190.9300
N3—C141.410 (7)C20—H200.9300
N3—H3A0.8600C21—C221.488 (8)
N4—C231.317 (14)C22—H22A0.9700
N4—C221.374 (8)C22—H22B0.9700
N4—H40.8600C23—C241.295 (19)
N5—C311.351 (7)C23—C281.468 (18)
N5—C301.410 (7)C24—C251.421 (15)
N5—H50.84 (5)C24—H240.9300
N7—C131.241 (7)C25—C261.293 (17)
N7—H7A0.8600C25—H250.9300
N8—C291.254 (7)C26—C271.476 (18)
N8—H80.79 (2)C26—H260.9300
N9—C211.295 (7)C27—C281.322 (14)
N9—Sm1i2.404 (4)C27—H270.9300
N9—H90.8600C28—H280.9300
C1—C21.384 (10)C29—C301.495 (8)
C1—H10.9300C30—H30A0.9700
C2—C31.340 (12)C30—H30B0.9700
C2—H20.9300C31—C321.353 (9)
C3—C41.338 (12)C31—C361.389 (9)
C3—H30.9300C32—C331.349 (10)
C4—C51.420 (10)C32—H320.9300
C4—C61.490 (12)C33—C341.404 (13)
C5—C91.421 (9)C33—H330.9300
C6—C71.303 (15)C34—C351.346 (12)
C6—H60.9300C34—H340.9300
C7—C81.407 (13)C35—C361.351 (10)
C7—H70.9300C35—H350.9300
C8—C101.362 (12)C36—H360.9300
O1—Sm1—N163.78 (13)N1—C5—C9118.6 (6)
O1—Sm1—N274.82 (13)C4—C5—C9119.6 (6)
O1—Sm1—N773.24 (13)C7—C6—C4120.6 (9)
O1—Sm1—N8139.47 (13)C7—C6—H6119.7
O1—Sm1—N947.76 (11)C4—C6—H6119.7
N1—Sm1—N259.51 (15)C6—C7—C8121.7 (8)
N1—Sm1—N7127.34 (13)C6—C7—H7119.1
N1—Sm1—N877.35 (14)C8—C7—H7119.1
N1—Sm1—N9102.57 (14)C10—C8—C7122.9 (7)
N2—Sm1—N781.57 (14)C10—C8—C9116.0 (7)
N2—Sm1—N895.78 (14)C7—C8—C9121.1 (8)
N2—Sm1—N9118.50 (12)N2—C9—C5118.1 (5)
N7—Sm1—N8145.52 (14)N2—C9—C8123.5 (6)
N7—Sm1—N964.51 (12)C5—C9—C8118.4 (6)
N8—Sm1—N9140.58 (12)C11—C10—C8120.5 (7)
N9i—Sm1—N888.03 (15)C11—C10—H10119.7
N9i—Sm1—N778.13 (13)C8—C10—H10119.7
N9i—Sm1—O2i74.09 (13)C10—C11—C12119.5 (7)
N8—Sm1—O2i76.88 (13)C10—C11—H11120.2
N7—Sm1—O2i127.41 (13)C12—C11—H11120.2
N9i—Sm1—O2i74.09 (13)N2—C12—C11122.5 (7)
N8—Sm1—O2i76.88 (13)N2—C12—H12118.8
N7—Sm1—O2i127.41 (13)C11—C12—H12118.8
O2i—Sm1—O2i0.0 (3)O2—C13—N7128.7 (5)
N9i—Sm1—O2i74.09 (13)O2—C13—C14119.6 (5)
N8—Sm1—O2i76.88 (13)N7—C13—C14111.6 (5)
N7—Sm1—O2i127.41 (13)N3—C14—C13109.7 (5)
O2i—Sm1—O2i0.0 (3)N3—C14—H14A109.7
O2i—Sm1—O2i0.0 (3)C13—C14—H14A109.7
N9i—Sm1—O3ii78.11 (14)N3—C14—H14B109.7
N8—Sm1—O3ii75.89 (13)C13—C14—H14B109.7
N7—Sm1—O3ii70.44 (13)H14A—C14—H14B108.2
O2i—Sm1—O3ii141.38 (13)C16—C15—C20123.0 (7)
O2i—Sm1—O3ii141.38 (13)C16—C15—N3113.8 (6)
O2i—Sm1—O3ii141.38 (13)C20—C15—N3123.2 (6)
N9i—Sm1—O1120.36 (14)C15—C16—C17118.3 (8)
O2i—Sm1—O183.67 (12)C15—C16—H16120.9
O2i—Sm1—O183.67 (12)C17—C16—H16120.9
O2i—Sm1—O183.67 (12)C18—C17—C16120.5 (9)
O3ii—Sm1—O1134.14 (12)C18—C17—H17119.8
N9i—Sm1—N2148.94 (15)C16—C17—H17119.8
O2i—Sm1—N2136.81 (14)C19—C18—C17121.2 (8)
O2i—Sm1—N2136.81 (14)C19—C18—H18119.4
O2i—Sm1—N2136.81 (14)C17—C18—H18119.4
O3ii—Sm1—N273.04 (15)C18—C19—C20119.1 (9)
N9i—Sm1—N1150.30 (14)C18—C19—H19120.5
O2i—Sm1—N177.45 (14)C20—C19—H19120.5
O2i—Sm1—N177.45 (14)C15—C20—C19117.9 (8)
O2i—Sm1—N177.45 (14)C15—C20—H20121.0
O3ii—Sm1—N1121.79 (15)C19—C20—H20121.0
N9i—Sm1—N972.79 (15)O1—C21—N9121.3 (5)
O2i—Sm1—N964.97 (12)O1—C21—C22122.9 (5)
O2i—Sm1—N964.97 (12)N9—C21—C22115.8 (5)
O2i—Sm1—N964.97 (12)N4—C22—C21113.7 (5)
O3ii—Sm1—N9130.08 (13)N4—C22—H22A108.8
N9i—Sm1—H884 (2)C21—C22—H22A108.8
N7—Sm1—H8155.0 (19)N4—C22—H22B108.8
O2i—Sm1—H861.7 (13)C21—C22—H22B108.8
O2i—Sm1—H861.7 (13)H22A—C22—H22B107.7
O2i—Sm1—H861.7 (13)C24—C23—N4127.9 (14)
O3ii—Sm1—H889.2 (15)C24—C23—C28121.5 (13)
O1—Sm1—H8131.4 (17)N4—C23—C28110.6 (13)
N2—Sm1—H8106.9 (17)C23—C24—C25119.3 (15)
N1—Sm1—H875 (2)C23—C24—H24120.4
N9—Sm1—H8125.7 (13)C25—C24—H24120.4
C21—O1—Sm1103.0 (3)C26—C25—C24118.3 (15)
C13—O2—Sm1i137.9 (4)C26—C25—H25120.8
C29—O3—Sm1ii150.2 (4)C24—C25—H25120.8
C1—N1—C5118.8 (6)C25—C26—C27126.2 (13)
C1—N1—Sm1119.5 (4)C25—C26—H26116.9
C5—N1—Sm1120.3 (4)C27—C26—H26116.9
C12—N2—C9117.8 (5)C28—C27—C26112.7 (13)
C12—N2—Sm1119.9 (4)C28—C27—H27123.6
C9—N2—Sm1122.0 (4)C26—C27—H27123.6
C15—N3—C14117.1 (5)C27—C28—C23121.8 (15)
C15—N3—H3A121.5C27—C28—H28119.1
C14—N3—H3A121.5C23—C28—H28119.1
C23—N4—C22114.4 (9)O3—C29—N8127.4 (5)
C23—N4—H4122.8O3—C29—C30119.9 (5)
C22—N4—H4122.8N8—C29—C30112.6 (5)
C31—N5—C30116.7 (5)N5—C30—C29110.6 (5)
C31—N5—H585.3 (17)N5—C30—H30A109.5
C30—N5—H599 (5)C29—C30—H30A109.5
C13—N7—Sm1131.0 (3)N5—C30—H30B109.5
C13—N7—H7A114.5C29—C30—H30B109.5
Sm1—N7—H7A114.5H30A—C30—H30B108.1
C29—N8—Sm1150.9 (4)N5—C31—C32124.9 (6)
C29—N8—H8120 (5)N5—C31—C36114.4 (6)
C21—N9—Sm1i163.3 (4)C32—C31—C36120.6 (6)
C21—N9—Sm187.8 (3)C32—C31—H5124 (3)
Sm1i—N9—Sm1107.21 (15)C36—C31—H5107 (3)
C21—N9—H998.3C33—C32—C31120.1 (7)
Sm1i—N9—H998.3C33—C32—H32120.0
N1—C1—C2122.5 (7)C31—C32—H32120.0
N1—C1—H1118.8C32—C33—C34119.7 (8)
C2—C1—H1118.8C32—C33—H33120.2
C3—C2—C1119.0 (8)C34—C33—H33120.2
C3—C2—H2120.5C35—C34—C33119.4 (7)
C1—C2—H2120.5C35—C34—H34120.3
C4—C3—C2120.8 (8)C33—C34—H34120.3
C4—C3—H3119.6C34—C35—C36121.2 (7)
C2—C3—H3119.6C34—C35—H35119.4
C3—C4—C5117.1 (7)C36—C35—H35119.4
C3—C4—C6124.6 (8)C35—C36—C31118.9 (7)
C5—C4—C6118.3 (8)C35—C36—H36120.5
N1—C5—C4121.8 (6)C31—C36—H36120.5
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
C1—H1···O2i0.932.413.100 (8)131
C10—H10···O1iii0.932.323.188 (8)155
C12—H12···O3ii0.932.453.039 (8)121
C12—H12···N5ii0.932.543.387 (9)151
C22—H22B···N8iv0.972.373.310 (8)162
N9—H9···O2i0.862.142.889 (6)146
N9—H9···N9i0.862.613.136 (9)120
N8—H8···O2i0.79 (2)2.31 (3)3.062 (6)160 (6)
N3—H3A···O20.862.242.595 (5)105
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z.
Selected geometric parameters (Å, º) top
Sm1—O12.561 (4)Sm1—N72.448 (4)
Sm1—O2i2.505 (4)Sm1—N82.418 (4)
Sm1—O3ii2.535 (4)Sm1—N9i2.404 (4)
Sm1—N12.713 (5)Sm1—N92.846 (5)
Sm1—N22.685 (5)
O1—Sm1—N163.78 (13)N1—Sm1—N9102.57 (14)
O1—Sm1—N274.82 (13)N2—Sm1—N781.57 (14)
O1—Sm1—N773.24 (13)N2—Sm1—N895.78 (14)
O1—Sm1—N8139.47 (13)N2—Sm1—N9118.50 (12)
O1—Sm1—N947.76 (11)N7—Sm1—N8145.52 (14)
N1—Sm1—N259.51 (15)N7—Sm1—N964.51 (12)
N1—Sm1—N7127.34 (13)N8—Sm1—N9140.58 (12)
N1—Sm1—N877.35 (14)
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
C1—H1···O2i0.932.413.100 (8)131
C10—H10···O1iii0.932.323.188 (8)155
C12—H12···O3ii0.932.453.039 (8)121
C12—H12···N5ii0.932.543.387 (9)151
C22—H22B···N8iv0.972.373.310 (8)162
N9—H9···O2i0.862.142.889 (6)146
N9—H9···N9i0.862.613.136 (9)120
N8—H8···O2i0.79 (2)2.31 (3)3.062 (6)160 (6)
N3—H3A···O20.862.242.595 (5)105
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z.
Acknowledgements top

The authors thank the Youth Programme of Jinggangshan University for financial support.

references
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