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Acta Cryst. (2008). E64, m1521    [ doi:10.1107/S1600536808036155 ]

Poly[(N,N-dimethylformamide-[kappa]O)tris([mu]-naphthalene-1-acetato)terbium(III)]

H.-T. Xia, Y.-F. Liu, Y.-Y. Zhang and D.-Q. Wang

Abstract top

In title compound, [Tb(C12H9O2)3(C3H7NO)]n, the Tb atom is nine-coordinated by nine O atoms from three naphthalene-1-acetate and one N,N-dimethylformamide ligands. The Tb atoms are linked by three bridging naphthalene-1-acetate ligands into a chain parallel to the b axis. Further stabilization of the structure is accomplished by non-classical C-H...O hydrogen bonds and C-H...[pi] interactions.

Comment top

As part of our ongoing research into the complexes between rare earth elements and naphthalene-1-acetato(NNA) and 1,10-phenanthroline(phen) ligands, we have recently reported the crystal structures of two complexes [Tb2(C12H9O2)6(C12H8N2)2].2C3H7NO (II) (Xia et al., 2007a) and [SmTb(C12H9O2)6(C12H8N2)2].2C3H7NO (III) (Xia et al., 2007b). We report here the crystal structures of a new rare earth complex with NAA, (I).

In the title complex (I), the coordination environment of the Tb atom and coordination modes of the NNA ligands coordinated to TbIII ion is in agreement with the complexes reported above (Fig. 1). The average bond lengths of between the terbium center and carboxylic oxygen atoms are 2.448 (4) Å, longer than those [2.426 (7) Å and 2.440 (5) Å] of complex (II) and (III), respectively. The dihedral angles between naphthyl ring (C3–C12 ring) and another naphthyl rings are 62.69 (12)°(C15–C24 ring) and 56.17 (12)° (C27–C36 ring).

In (I), Tb atoms are linked by three naphthalene-1-acetato into a chain parallel to the b axis. Neighbouring chains are linked into a three-dimensional network by van Waals forces.

Related literature top

For related structures, see: Xia et al. (2007a,b)

Experimental top

To a stirred solution of 1-naphthylacetic acid (0.5586 g, 3 mmol) in 30 ml methanol, and a solution of Tb(NO3)3.6H2O (0.453 g, 1.0 mmol) in water (10 ml) was added. The mixed solution was heated to 333 K and stirred for 3 h, and then cooled to room temperature. The precipitate was washed with water and then dissolved in DMF. A colourless crystal suitable for X-ray diffraction was obtained by evaporation of DMF solution.

Refinement top

All H atoms were located in difference Fourier maps. H atoms bonded to C atoms were treated as riding atoms, with C—H distances of 0.93 Å (aromatic formyl), 0.97 Å (methylene) and 0.96 Å (methyl) and Uiso(H) = 1.2 (aromatic formyl methylene) or 1.5 Ueq(C) (methyl).

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level, H atoms have been omitted. [Symmetry codes: (A) 1 - x, 1/2 + y, 1/2 - z].
Poly[(N,N-dimethylformamide-κO)tris(µ-naphthalene-1- acetato)terbium(III)] top
Crystal data top
[Tb(C12H9O2)3(C3H7NO)]F(000) = 1584
Mr = 787.59Dx = 1.606 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5059 reflections
a = 17.6484 (18) Åθ = 2.4–27.5°
b = 7.8854 (10) ŵ = 2.23 mm−1
c = 24.184 (3) ÅT = 298 K
β = 104.613 (2)°Block, colourless
V = 3256.7 (6) Å30.32 × 0.17 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		5733 independent reflections
Radiation source: fine-focus sealed tube4274 reflections with I > 2σ(I)
graphiteRint = 0.049
φ and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −20→17
Tmin = 0.536, Tmax = 0.808k = −9→9
15719 measured reflectionsl = −28→28
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0533P)2 + 2.7161P]
where P = (Fo2 + 2Fc2)/3
5733 reflections(Δ/σ)max = 0.001
435 parametersΔρmax = 1.17 e Å−3
0 restraintsΔρmin = −1.59 e Å−3
Crystal data top
[Tb(C12H9O2)3(C3H7NO)]V = 3256.7 (6) Å3
Mr = 787.59Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.6484 (18) ŵ = 2.23 mm−1
b = 7.8854 (10) ÅT = 298 K
c = 24.184 (3) Å0.32 × 0.17 × 0.10 mm
β = 104.613 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		5733 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4274 reflections with I > 2σ(I)
Tmin = 0.536, Tmax = 0.808Rint = 0.049
15719 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.106Δρmax = 1.17 e Å−3
S = 1.02Δρmin = −1.59 e Å−3
5733 reflectionsAbsolute structure: ?
435 parametersFlack parameter: ?
0 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
Tb10.524810 (16)0.42775 (4)0.272830 (11)0.02364 (11)
N10.7253 (3)0.2677 (8)0.4209 (2)0.0470 (15)
O10.4761 (2)0.1248 (5)0.30008 (18)0.0339 (10)
O20.4655 (3)0.3527 (6)0.34879 (18)0.0390 (11)
O30.3993 (2)0.3832 (6)0.21354 (18)0.0380 (11)
O40.3868 (2)0.1228 (5)0.17513 (18)0.0348 (11)
O50.5499 (2)0.1847 (5)0.21524 (16)0.0309 (10)
O60.6464 (2)0.3687 (6)0.23763 (19)0.0381 (11)
O70.6182 (3)0.2771 (6)0.34752 (19)0.0437 (12)
C10.4615 (4)0.1964 (9)0.3431 (3)0.0354 (16)
C20.4441 (5)0.0852 (9)0.3892 (3)0.0484 (19)
H2A0.49270.03590.41120.058*
H2B0.4103−0.00690.37130.058*
C30.4052 (5)0.1789 (10)0.4294 (3)0.056 (2)
C40.4480 (6)0.2148 (11)0.4841 (3)0.067 (2)
H40.49980.17970.49670.080*
C50.4107 (7)0.3091 (13)0.5221 (4)0.080 (3)
H50.43820.33650.55920.096*
C60.3359 (7)0.3546 (13)0.5022 (5)0.081 (3)
H60.31290.41370.52710.098*
C70.2894 (7)0.3223 (11)0.4482 (5)0.072 (3)
C80.3263 (6)0.2311 (10)0.4100 (4)0.059 (2)
C90.2801 (6)0.2008 (11)0.3545 (4)0.066 (2)
H90.30170.13980.32930.079*
C100.2047 (6)0.2572 (12)0.3361 (5)0.080 (3)
H100.17680.23880.29850.096*
C110.1701 (7)0.3416 (14)0.3733 (6)0.088 (3)
H110.11830.37700.36090.105*
C120.2101 (7)0.3724 (12)0.4265 (5)0.076 (3)
H120.18530.42930.45060.091*
C130.3652 (3)0.2728 (9)0.1786 (3)0.0301 (15)
C140.2921 (4)0.3284 (9)0.1342 (3)0.0366 (16)
H14A0.28460.44880.13900.044*
H14B0.30090.31200.09660.044*
C150.2176 (4)0.2374 (8)0.1364 (3)0.0357 (16)
C160.2114 (4)0.1483 (9)0.1830 (3)0.0458 (18)
H160.25490.13890.21390.055*
C170.1408 (5)0.0696 (10)0.1858 (4)0.063 (2)
H170.13810.00690.21790.075*
C180.0766 (5)0.0864 (11)0.1410 (4)0.063 (2)
H180.02960.03760.14360.075*
C190.0788 (4)0.1738 (11)0.0917 (4)0.056 (2)
C200.1505 (4)0.2507 (9)0.0887 (3)0.0427 (18)
C210.1516 (4)0.3357 (10)0.0381 (3)0.051 (2)
H210.19800.38640.03520.061*
C220.0872 (5)0.3475 (12)−0.0073 (4)0.066 (2)
H220.08960.4057−0.04030.079*
C230.0173 (5)0.2690 (12)−0.0027 (4)0.077 (3)
H23−0.02680.2749−0.03330.092*
C240.0130 (5)0.1872 (12)0.0440 (4)0.069 (3)
H24−0.03410.13730.04560.082*
C250.6191 (4)0.2342 (8)0.2145 (3)0.0319 (15)
C260.6633 (4)0.1225 (9)0.1826 (3)0.0477 (19)
H26A0.62960.09980.14490.057*
H26B0.67370.01490.20250.057*
C270.7401 (4)0.1926 (9)0.1754 (3)0.0455 (19)
C280.7411 (5)0.2700 (10)0.1254 (4)0.053 (2)
H280.69430.28270.09760.063*
C290.8106 (5)0.3315 (11)0.1143 (4)0.061 (2)
H290.80920.38410.07960.073*
C300.8794 (5)0.3141 (10)0.1539 (4)0.059 (2)
H300.92530.35260.14580.071*
C310.8830 (4)0.2387 (10)0.2073 (4)0.052 (2)
C320.8112 (4)0.1781 (9)0.2182 (3)0.0488 (19)
C330.8159 (5)0.1038 (10)0.2716 (4)0.058 (2)
H330.77040.06410.28000.069*
C340.8852 (6)0.0884 (11)0.3115 (4)0.072 (3)
H340.88650.03770.34640.087*
C350.9549 (6)0.1483 (12)0.3005 (5)0.078 (3)
H351.00210.13800.32800.094*
C360.9526 (5)0.2211 (12)0.2494 (4)0.068 (2)
H360.99890.26050.24230.081*
C370.6886 (4)0.3035 (9)0.3681 (3)0.0412 (17)
H370.71730.35180.34480.049*
C380.6820 (5)0.2000 (12)0.4591 (3)0.067 (2)
H38A0.62700.20520.44120.101*
H38B0.69320.26540.49370.101*
H38C0.69710.08410.46790.101*
C390.8097 (4)0.2947 (11)0.4423 (4)0.067 (2)
H39A0.83110.33110.41150.100*
H39B0.83430.19060.45790.100*
H39C0.81910.38010.47150.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Tb10.02147 (16)0.02162 (17)0.02753 (16)−0.00010 (14)0.00560 (11)−0.00052 (14)
N10.039 (4)0.049 (4)0.046 (4)0.000 (3)−0.001 (3)−0.005 (3)
O10.035 (3)0.035 (3)0.034 (2)0.000 (2)0.013 (2)−0.002 (2)
O20.050 (3)0.031 (3)0.042 (3)0.005 (2)0.024 (2)0.006 (2)
O30.029 (3)0.037 (3)0.042 (3)0.001 (2)−0.003 (2)−0.006 (2)
O40.040 (3)0.023 (3)0.038 (3)0.005 (2)0.003 (2)0.0023 (19)
O50.030 (2)0.029 (3)0.037 (2)−0.0011 (19)0.016 (2)−0.003 (2)
O60.032 (3)0.032 (3)0.054 (3)−0.005 (2)0.018 (2)−0.010 (2)
O70.034 (3)0.038 (3)0.054 (3)−0.002 (2)0.002 (2)0.010 (2)
C10.038 (4)0.034 (4)0.039 (4)0.003 (3)0.017 (3)0.004 (3)
C20.069 (5)0.039 (4)0.047 (4)0.003 (4)0.031 (4)0.005 (4)
C30.084 (6)0.041 (5)0.056 (5)−0.004 (4)0.040 (5)0.011 (4)
C40.097 (7)0.053 (6)0.060 (6)0.000 (5)0.039 (5)0.004 (4)
C50.125 (10)0.068 (7)0.056 (6)−0.007 (7)0.040 (6)0.003 (5)
C60.114 (9)0.057 (6)0.089 (8)0.005 (6)0.057 (7)0.007 (6)
C70.098 (8)0.047 (6)0.087 (7)−0.003 (5)0.057 (6)0.015 (5)
C80.082 (7)0.040 (5)0.073 (6)−0.003 (4)0.051 (5)0.011 (4)
C90.079 (7)0.049 (6)0.082 (7)0.000 (5)0.041 (6)0.011 (5)
C100.085 (8)0.058 (6)0.105 (8)0.000 (6)0.038 (6)0.010 (6)
C110.089 (8)0.065 (7)0.121 (10)0.001 (6)0.049 (8)0.018 (7)
C120.091 (8)0.055 (6)0.103 (8)0.007 (5)0.064 (7)0.009 (6)
C130.020 (3)0.036 (4)0.034 (4)−0.002 (3)0.006 (3)0.007 (3)
C140.032 (4)0.029 (4)0.044 (4)−0.002 (3)0.002 (3)0.006 (3)
C150.029 (4)0.028 (4)0.050 (4)0.003 (3)0.012 (3)0.000 (3)
C160.037 (4)0.041 (4)0.061 (5)0.006 (3)0.015 (4)0.004 (4)
C170.056 (6)0.051 (5)0.087 (6)−0.005 (4)0.031 (5)0.008 (5)
C180.038 (5)0.055 (6)0.098 (7)−0.003 (4)0.021 (5)−0.004 (5)
C190.034 (5)0.050 (5)0.081 (6)0.004 (4)0.010 (4)−0.012 (5)
C200.030 (4)0.033 (4)0.064 (5)0.003 (3)0.009 (3)−0.009 (4)
C210.032 (4)0.050 (5)0.062 (5)0.004 (4)−0.004 (4)−0.005 (4)
C220.046 (5)0.074 (6)0.068 (6)0.010 (5)−0.003 (4)−0.003 (5)
C230.049 (6)0.076 (7)0.090 (7)0.004 (5)−0.012 (5)−0.013 (6)
C240.038 (5)0.063 (6)0.097 (7)−0.001 (4)0.001 (5)−0.009 (6)
C250.032 (4)0.026 (4)0.043 (4)0.001 (3)0.019 (3)0.001 (3)
C260.040 (4)0.038 (4)0.073 (5)−0.004 (3)0.029 (4)−0.015 (4)
C270.042 (4)0.035 (4)0.067 (5)−0.005 (3)0.029 (4)−0.016 (4)
C280.052 (5)0.049 (5)0.066 (5)−0.004 (4)0.029 (4)−0.011 (4)
C290.068 (6)0.053 (6)0.070 (6)−0.007 (5)0.034 (5)−0.011 (5)
C300.057 (6)0.052 (6)0.081 (6)−0.013 (4)0.042 (5)−0.014 (5)
C310.044 (5)0.040 (5)0.080 (6)−0.003 (4)0.030 (4)−0.014 (4)
C320.048 (5)0.033 (4)0.073 (5)−0.001 (4)0.029 (4)−0.011 (4)
C330.058 (6)0.040 (5)0.081 (6)−0.002 (4)0.028 (5)−0.002 (4)
C340.079 (7)0.050 (6)0.087 (7)−0.001 (5)0.018 (6)0.007 (5)
C350.064 (7)0.059 (6)0.105 (8)0.007 (5)0.009 (6)−0.006 (6)
C360.055 (6)0.055 (6)0.096 (7)0.000 (4)0.025 (5)−0.011 (5)
C370.038 (4)0.031 (4)0.052 (5)−0.002 (3)0.006 (4)0.000 (3)
C380.070 (6)0.082 (7)0.047 (5)0.015 (5)0.008 (4)0.002 (5)
C390.032 (4)0.069 (6)0.086 (6)−0.002 (4)−0.013 (4)−0.005 (5)
Geometric parameters (Å, °) top
Tb1—O4i2.322 (4)C15—C161.357 (9)
Tb1—O32.341 (4)C15—C201.433 (9)
Tb1—O1i2.348 (4)C16—C171.409 (10)
Tb1—O22.407 (4)C16—H160.9300
Tb1—O72.427 (4)C17—C181.363 (12)
Tb1—O5i2.473 (4)C17—H170.9300
Tb1—O52.474 (4)C18—C191.387 (11)
Tb1—O62.542 (4)C18—H180.9300
Tb1—O12.677 (4)C19—C241.420 (10)
N1—C371.307 (8)C19—C201.421 (10)
N1—C381.442 (9)C20—C211.399 (10)
N1—C391.465 (8)C21—C221.370 (10)
O1—C11.265 (7)C21—H210.9300
O1—Tb1ii2.348 (4)C22—C231.410 (12)
O2—C11.240 (8)C22—H220.9300
O3—C131.256 (7)C23—C241.319 (12)
O4—C131.252 (7)C23—H230.9300
O4—Tb1ii2.322 (4)C24—H240.9300
O5—C251.287 (7)C25—C261.510 (9)
O5—Tb1ii2.473 (4)C26—C271.514 (9)
O6—C251.239 (7)C26—H26A0.9700
O7—C371.234 (7)C26—H26B0.9700
C1—C21.509 (9)C27—C281.359 (10)
C2—C31.517 (10)C27—C321.416 (10)
C2—H2A0.9700C28—C291.406 (10)
C2—H2B0.9700C28—H280.9300
C3—C41.377 (11)C29—C301.351 (11)
C3—C81.413 (11)C29—H290.9300
C4—C51.462 (12)C30—C311.408 (11)
C4—H40.9300C30—H300.9300
C5—C61.335 (13)C31—C361.391 (11)
C5—H50.9300C31—C321.439 (10)
C6—C71.379 (13)C32—C331.403 (10)
C6—H60.9300C33—C341.358 (12)
C7—C121.422 (13)C33—H330.9300
C7—C81.449 (11)C34—C351.404 (12)
C8—C91.404 (12)C34—H340.9300
C9—C101.367 (12)C35—C361.353 (12)
C9—H90.9300C35—H350.9300
C10—C111.379 (13)C36—H360.9300
C10—H100.9300C37—H370.9300
C11—C121.324 (13)C38—H38A0.9600
C11—H110.9300C38—H38B0.9600
C12—H120.9300C38—H38C0.9600
C13—C141.520 (8)C39—H39A0.9600
C14—C151.509 (9)C39—H39B0.9600
C14—H14A0.9700C39—H39C0.9600
C14—H14B0.9700
O4i—Tb1—O3146.45 (15)O3—C13—C14116.9 (6)
O4i—Tb1—O1i81.07 (15)C15—C14—C13115.5 (5)
O3—Tb1—O1i79.23 (15)C15—C14—H14A108.4
O4i—Tb1—O296.39 (16)C13—C14—H14A108.4
O3—Tb1—O284.51 (16)C15—C14—H14B108.4
O1i—Tb1—O2144.54 (15)C13—C14—H14B108.4
O4i—Tb1—O771.57 (16)H14A—C14—H14B107.5
O3—Tb1—O7137.93 (16)C16—C15—C20118.9 (6)
O1i—Tb1—O7139.27 (15)C16—C15—C14121.9 (6)
O2—Tb1—O769.87 (15)C20—C15—C14119.2 (6)
O4i—Tb1—O5i72.48 (14)C15—C16—C17121.8 (7)
O3—Tb1—O5i75.20 (14)C15—C16—H16119.1
O1i—Tb1—O5i69.06 (14)C17—C16—H16119.1
O2—Tb1—O5i76.42 (14)C18—C17—C16119.1 (8)
O7—Tb1—O5i126.59 (15)C18—C17—H17120.4
O4i—Tb1—O5128.86 (14)C16—C17—H17120.4
O3—Tb1—O579.33 (14)C17—C18—C19122.3 (8)
O1i—Tb1—O593.34 (14)C17—C18—H18118.9
O2—Tb1—O5114.40 (15)C19—C18—H18118.9
O7—Tb1—O581.68 (15)C18—C19—C24122.8 (8)
O5i—Tb1—O5151.24 (3)C18—C19—C20118.4 (7)
O4i—Tb1—O678.16 (15)C24—C19—C20118.9 (8)
O3—Tb1—O6121.00 (15)C21—C20—C19117.3 (7)
O1i—Tb1—O673.50 (14)C21—C20—C15123.2 (6)
O2—Tb1—O6140.97 (15)C19—C20—C15119.6 (7)
O7—Tb1—O671.80 (15)C22—C21—C20122.8 (8)
O5i—Tb1—O6135.12 (14)C22—C21—H21118.6
O5—Tb1—O651.96 (13)C20—C21—H21118.6
O4i—Tb1—O1132.16 (14)C21—C22—C23118.2 (9)
O3—Tb1—O172.78 (14)C21—C22—H22120.9
O1i—Tb1—O1146.51 (8)C23—C22—H22120.9
O2—Tb1—O150.50 (14)C24—C23—C22121.6 (9)
O7—Tb1—O165.16 (14)C24—C23—H23119.2
O5i—Tb1—O1119.23 (13)C22—C23—H23119.2
O5—Tb1—O163.99 (13)C23—C24—C19121.3 (9)
O6—Tb1—O1105.65 (13)C23—C24—H24119.3
C37—N1—C38119.6 (6)C19—C24—H24119.3
C37—N1—C39121.6 (7)O6—C25—O5121.0 (6)
C38—N1—C39118.9 (6)O6—C25—C26122.6 (6)
C1—O1—Tb1ii161.5 (4)O5—C25—C26116.4 (6)
C1—O1—Tb187.1 (4)C25—C26—C27116.0 (6)
Tb1ii—O1—Tb1110.33 (15)C25—C26—H26A108.3
C1—O2—Tb1100.5 (4)C27—C26—H26A108.3
C13—O3—Tb1137.3 (4)C25—C26—H26B108.3
C13—O4—Tb1ii139.8 (4)C27—C26—H26B108.3
C25—O5—Tb1ii141.8 (4)H26A—C26—H26B107.4
C25—O5—Tb194.5 (4)C28—C27—C32118.6 (7)
Tb1ii—O5—Tb1113.12 (15)C28—C27—C26118.7 (7)
C25—O6—Tb192.5 (4)C32—C27—C26122.7 (7)
C37—O7—Tb1130.1 (4)C27—C28—C29122.3 (8)
O2—C1—O1121.1 (6)C27—C28—H28118.9
O2—C1—C2120.7 (6)C29—C28—H28118.9
O1—C1—C2118.0 (6)C30—C29—C28120.0 (8)
C1—C2—C3113.6 (6)C30—C29—H29120.0
C1—C2—H2A108.8C28—C29—H29120.0
C3—C2—H2A108.8C29—C30—C31121.2 (7)
C1—C2—H2B108.8C29—C30—H30119.4
C3—C2—H2B108.8C31—C30—H30119.4
H2A—C2—H2B107.7C36—C31—C30122.7 (8)
C4—C3—C8121.0 (8)C36—C31—C32119.2 (8)
C4—C3—C2119.3 (8)C30—C31—C32118.0 (8)
C8—C3—C2119.7 (8)C33—C32—C27122.8 (7)
C3—C4—C5118.9 (9)C33—C32—C31117.2 (8)
C3—C4—H4120.5C27—C32—C31119.9 (7)
C5—C4—H4120.5C34—C33—C32121.6 (8)
C6—C5—C4118.1 (9)C34—C33—H33119.2
C6—C5—H5120.9C32—C33—H33119.2
C4—C5—H5120.9C33—C34—C35120.7 (9)
C5—C6—C7126.1 (10)C33—C34—H34119.6
C5—C6—H6117.0C35—C34—H34119.6
C7—C6—H6117.0C36—C35—C34119.3 (9)
C6—C7—C12126.4 (10)C36—C35—H35120.4
C6—C7—C8116.1 (10)C34—C35—H35120.4
C12—C7—C8117.5 (10)C35—C36—C31121.9 (9)
C9—C8—C3123.7 (8)C35—C36—H36119.1
C9—C8—C7116.6 (9)C31—C36—H36119.1
C3—C8—C7119.7 (9)O7—C37—N1123.9 (7)
C10—C9—C8122.7 (9)O7—C37—H37118.0
C10—C9—H9118.7N1—C37—H37118.0
C8—C9—H9118.7N1—C38—H38A109.5
C9—C10—C11119.9 (11)N1—C38—H38B109.5
C9—C10—H10120.0H38A—C38—H38B109.5
C11—C10—H10120.0N1—C38—H38C109.5
C12—C11—C10120.4 (11)H38A—C38—H38C109.5
C12—C11—H11119.8H38B—C38—H38C109.5
C10—C11—H11119.8N1—C39—H39A109.5
C11—C12—C7122.9 (10)N1—C39—H39B109.5
C11—C12—H12118.6H39A—C39—H39B109.5
C7—C12—H12118.6N1—C39—H39C109.5
O4—C13—O3126.7 (6)H39A—C39—H39C109.5
O4—C13—C14116.3 (6)H39B—C39—H39C109.5
O4i—Tb1—O1—C151.7 (4)C5—C6—C7—C8−0.3 (15)
O3—Tb1—O1—C1−102.0 (4)C4—C3—C8—C9178.9 (8)
O1i—Tb1—O1—C1−136.6 (4)C2—C3—C8—C90.3 (11)
O2—Tb1—O1—C1−4.7 (4)C4—C3—C8—C7−0.6 (12)
O7—Tb1—O1—C179.0 (4)C2—C3—C8—C7−179.3 (7)
O5i—Tb1—O1—C1−40.6 (4)C6—C7—C8—C9−178.7 (8)
O5—Tb1—O1—C1171.7 (4)C12—C7—C8—C90.2 (11)
O6—Tb1—O1—C1139.8 (4)C6—C7—C8—C30.9 (12)
O4i—Tb1—O1—Tb1ii−134.69 (18)C12—C7—C8—C3179.8 (7)
O3—Tb1—O1—Tb1ii71.61 (18)C3—C8—C9—C10−177.8 (8)
O1i—Tb1—O1—Tb1ii37.0 (2)C7—C8—C9—C101.7 (12)
O2—Tb1—O1—Tb1ii168.8 (3)C8—C9—C10—C11−2.8 (14)
O7—Tb1—O1—Tb1ii−107.5 (2)C9—C10—C11—C121.8 (15)
O5i—Tb1—O1—Tb1ii132.94 (15)C10—C11—C12—C70.1 (16)
O5—Tb1—O1—Tb1ii−14.70 (14)C6—C7—C12—C11177.6 (10)
O6—Tb1—O1—Tb1ii−46.63 (19)C8—C7—C12—C11−1.1 (14)
O4i—Tb1—O2—C1−136.6 (4)Tb1ii—O4—C13—O313.1 (11)
O3—Tb1—O2—C177.1 (4)Tb1ii—O4—C13—C14−169.7 (4)
O1i—Tb1—O2—C1139.8 (4)Tb1—O3—C13—O419.4 (10)
O7—Tb1—O2—C1−69.0 (4)Tb1—O3—C13—C14−157.8 (4)
O5i—Tb1—O2—C1153.2 (4)O4—C13—C14—C1563.9 (8)
O5—Tb1—O2—C11.4 (4)O3—C13—C14—C15−118.6 (6)
O6—Tb1—O2—C1−57.6 (5)C13—C14—C15—C1617.4 (10)
O1—Tb1—O2—C14.9 (4)C13—C14—C15—C20−165.0 (6)
O4i—Tb1—O3—C13160.7 (5)C20—C15—C16—C17−0.3 (11)
O1i—Tb1—O3—C13105.6 (6)C14—C15—C16—C17177.2 (7)
O2—Tb1—O3—C13−106.0 (6)C15—C16—C17—C18−1.4 (12)
O7—Tb1—O3—C13−54.5 (7)C16—C17—C18—C192.2 (13)
O5i—Tb1—O3—C13176.6 (6)C17—C18—C19—C24177.7 (8)
O5—Tb1—O3—C1310.1 (6)C17—C18—C19—C20−1.2 (12)
O6—Tb1—O3—C1342.5 (6)C18—C19—C20—C21179.0 (7)
O1—Tb1—O3—C13−55.8 (6)C24—C19—C20—C21−0.1 (11)
O4i—Tb1—O5—C25−14.3 (4)C18—C19—C20—C15−0.6 (11)
O3—Tb1—O5—C25145.3 (4)C24—C19—C20—C15−179.6 (7)
O1i—Tb1—O5—C2566.9 (4)C16—C15—C20—C21−178.2 (7)
O2—Tb1—O5—C25−135.8 (3)C14—C15—C20—C214.2 (10)
O7—Tb1—O5—C25−72.4 (4)C16—C15—C20—C191.3 (10)
O5i—Tb1—O5—C25117.3 (3)C14—C15—C20—C19−176.3 (6)
O6—Tb1—O5—C250.9 (3)C19—C20—C21—C220.3 (11)
O1—Tb1—O5—C25−138.8 (4)C15—C20—C21—C22179.8 (7)
O4i—Tb1—O5—Tb1ii138.69 (17)C20—C21—C22—C23−0.6 (13)
O3—Tb1—O5—Tb1ii−61.71 (17)C21—C22—C23—C240.6 (14)
O1i—Tb1—O5—Tb1ii−140.09 (17)C22—C23—C24—C19−0.3 (15)
O2—Tb1—O5—Tb1ii17.2 (2)C18—C19—C24—C23−178.9 (9)
O7—Tb1—O5—Tb1ii80.57 (18)C20—C19—C24—C230.1 (13)
O5i—Tb1—O5—Tb1ii−89.7 (3)Tb1—O6—C25—O51.7 (6)
O6—Tb1—O5—Tb1ii153.9 (3)Tb1—O6—C25—C26179.9 (6)
O1—Tb1—O5—Tb1ii14.21 (14)Tb1ii—O5—C25—O6−139.3 (5)
O4i—Tb1—O6—C25166.9 (4)Tb1—O5—C25—O6−1.8 (6)
O3—Tb1—O6—C25−42.9 (4)Tb1ii—O5—C25—C2642.5 (9)
O1i—Tb1—O6—C25−109.0 (4)Tb1—O5—C25—C26179.9 (5)
O2—Tb1—O6—C2581.4 (4)O6—C25—C26—C27−5.8 (11)
O7—Tb1—O6—C2592.7 (4)O5—C25—C26—C27172.4 (6)
O5i—Tb1—O6—C25−143.3 (4)C25—C26—C27—C28−97.8 (8)
O5—Tb1—O6—C25−1.0 (3)C25—C26—C27—C3283.4 (9)
O1—Tb1—O6—C2536.1 (4)C32—C27—C28—C291.8 (11)
O4i—Tb1—O7—C37−34.6 (6)C26—C27—C28—C29−177.0 (7)
O3—Tb1—O7—C37165.0 (5)C27—C28—C29—C300.2 (12)
O1i—Tb1—O7—C3715.7 (7)C28—C29—C30—C31−1.6 (13)
O2—Tb1—O7—C37−138.9 (6)C29—C30—C31—C36−179.0 (8)
O5i—Tb1—O7—C37−84.7 (6)C29—C30—C31—C320.9 (12)
O5—Tb1—O7—C37101.2 (6)C28—C27—C32—C33178.6 (7)
O6—Tb1—O7—C3748.6 (6)C26—C27—C32—C33−2.6 (11)
O1—Tb1—O7—C37166.3 (6)C28—C27—C32—C31−2.5 (11)
Tb1—O2—C1—O1−9.4 (7)C26—C27—C32—C31176.3 (6)
Tb1—O2—C1—C2166.5 (5)C36—C31—C32—C330.1 (11)
Tb1ii—O1—C1—O2−152.4 (10)C30—C31—C32—C33−179.8 (7)
Tb1—O1—C1—O28.3 (6)C36—C31—C32—C27−179.0 (7)
Tb1ii—O1—C1—C231.6 (17)C30—C31—C32—C271.1 (11)
Tb1—O1—C1—C2−167.7 (6)C27—C32—C33—C34178.6 (8)
O2—C1—C2—C320.5 (10)C31—C32—C33—C34−0.4 (11)
O1—C1—C2—C3−163.4 (7)C32—C33—C34—C350.5 (13)
C1—C2—C3—C4−106.7 (8)C33—C34—C35—C36−0.4 (14)
C1—C2—C3—C872.0 (9)C34—C35—C36—C310.1 (14)
C8—C3—C4—C5−0.3 (12)C30—C31—C36—C35180.0 (8)
C2—C3—C4—C5178.4 (7)C32—C31—C36—C350.1 (13)
C3—C4—C5—C60.8 (13)Tb1—O7—C37—N1149.8 (5)
C4—C5—C6—C7−0.5 (16)C38—N1—C37—O7−2.9 (11)
C5—C6—C7—C12−179.1 (10)C39—N1—C37—O7177.2 (7)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C37—H37···O60.932.583.098 (8)116
C38—H38A···O70.962.302.718 (9)105
C17—H17···Cg1ii0.932.813.534 (9)135
C39—H39A···Cg2i0.962.933.670 (10)135
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (i) −x+1, y+1/2, −z+1/2.
Table 1
Selected geometric parameters (Å) top
Tb1—O4i2.322 (4)Tb1—O5i2.473 (4)
Tb1—O32.341 (4)Tb1—O52.474 (4)
Tb1—O1i2.348 (4)Tb1—O62.542 (4)
Tb1—O22.407 (4)Tb1—O12.677 (4)
Tb1—O72.427 (4)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C37—H37···O60.932.583.098 (8)116
C38—H38A···O70.962.302.718 (9)105
C17—H17···Cg1ii0.932.813.534 (9)135
C39—H39A···Cg2i0.962.933.670 (10)135
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (i) −x+1, y+1/2, −z+1/2.
Acknowledgements top

We acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

references
References top

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

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

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

Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007a). Acta Cryst. E63, m2624.

Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007b). Acta Cryst. E63, m2797–m2798.