Poly[(N,N-dimethyl­formamide-κO)tris­(μ-naphthalene-1-acetato)terbium(III)]

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

doi:10.1107/S1600536808036155

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1521

doi:10.1107/S1600536808036155

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Poly[(N,N-dimethylformamide-κO)tris(μ-naphthalene-1-acetato)terbium(III)]

Hai-Tao Xia,^a ^* Yu-Fen Liu,^a Ying-Ying Zhang ^b and Da-Qi Wang ^c

^aSchool of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^bBeilun Entry-Exit Inspection and Quarantine Bureau of China, Ningbo, Zhejiang, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong, 252059, People's Republic of China
^*Correspondence e-mail: xht161006@hhit.edu.cn

(Received 2 November 2008; accepted 4 November 2008; online 8 November 2008)

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⋯π interactions.

Related literature

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

Experimental

Crystal data

[Tb(C₁₂H₉O₂)₃(C₃H₇NO)]
M_r = 787.59
Monoclinic, P 2₁ /c
a = 17.6484 (18) Å
b = 7.8854 (10) Å
c = 24.184 (3) Å
β = 104.613 (2)°
V = 3256.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.23 mm⁻¹
T = 298 (2) K
0.32 × 0.17 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.536, T_max = 0.808
15719 measured reflections
5733 independent reflections
4274 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.106
S = 1.02
5733 reflections
435 parameters
H-atom parameters constrained
Δρ_max = 1.17 e Å⁻³
Δρ_min = −1.59 e Å⁻³

Table 1
Selected bond lengths (Å)

Tb1—O4ⁱ	2.322 (4)
Tb1—O3	2.341 (4)
Tb1—O1ⁱ	2.348 (4)
Tb1—O2	2.407 (4)
Tb1—O7	2.427 (4)
Tb1—O5ⁱ	2.473 (4)
Tb1—O5	2.474 (4)
Tb1—O6	2.542 (4)
Tb1—O1	2.677 (4)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C37—H37⋯O6	0.93	2.58	3.098 (8)	116
C38—H38A⋯O7	0.96	2.30	2.718 (9)	105
C17—H17⋯Cg1ⁱⁱ	0.93	2.81	3.534 (9)	135
C39—H39A⋯Cg2ⁱ	0.96	2.93	3.670 (10)	135
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C31–C36 and C15–C20 rings, respectively.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808036155/at2670sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036155/at2670Isup2.hkl

checkCIF report

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 Tb^III 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.

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

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
M_r = 787.59	D_x = 1.606 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5059 reflections
a = 17.6484 (18) Å	θ = 2.4–27.5°
b = 7.8854 (10) Å	µ = 2.23 mm⁻¹
c = 24.184 (3) Å	T = 298 K
β = 104.613 (2)°	Block, colourless
V = 3256.7 (6) Å³	0.32 × 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 tube	4274 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→17
T_min = 0.536, T_max = 0.808	k = −9→9
15719 measured reflections	l = −28→28

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0533P)² + 2.7161P] where P = (F_o² + 2F_c²)/3
5733 reflections	(Δ/σ)_max = 0.001
435 parameters	Δρ_max = 1.17 e Å⁻³
0 restraints	Δρ_min = −1.59 e Å⁻³

Crystal data top

[Tb(C₁₂H₉O₂)₃(C₃H₇NO)]	V = 3256.7 (6) Å³
M_r = 787.59	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.6484 (18) Å	µ = 2.23 mm⁻¹
b = 7.8854 (10) Å	T = 298 K
c = 24.184 (3) Å	0.32 × 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)
T_min = 0.536, T_max = 0.808	R_int = 0.049
15719 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.02	Δρ_max = 1.17 e Å⁻³
5733 reflections	Δρ_min = −1.59 e Å⁻³
435 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
Tb1	0.524810 (16)	0.42775 (4)	0.272830 (11)	0.02364 (11)
N1	0.7253 (3)	0.2677 (8)	0.4209 (2)	0.0470 (15)
O1	0.4761 (2)	0.1248 (5)	0.30008 (18)	0.0339 (10)
O2	0.4655 (3)	0.3527 (6)	0.34879 (18)	0.0390 (11)
O3	0.3993 (2)	0.3832 (6)	0.21354 (18)	0.0380 (11)
O4	0.3868 (2)	0.1228 (5)	0.17513 (18)	0.0348 (11)
O5	0.5499 (2)	0.1847 (5)	0.21524 (16)	0.0309 (10)
O6	0.6464 (2)	0.3687 (6)	0.23763 (19)	0.0381 (11)
O7	0.6182 (3)	0.2771 (6)	0.34752 (19)	0.0437 (12)
C1	0.4615 (4)	0.1964 (9)	0.3431 (3)	0.0354 (16)
C2	0.4441 (5)	0.0852 (9)	0.3892 (3)	0.0484 (19)
H2A	0.4927	0.0359	0.4112	0.058*
H2B	0.4103	−0.0069	0.3713	0.058*
C3	0.4052 (5)	0.1789 (10)	0.4294 (3)	0.056 (2)
C4	0.4480 (6)	0.2148 (11)	0.4841 (3)	0.067 (2)
H4	0.4998	0.1797	0.4967	0.080*
C5	0.4107 (7)	0.3091 (13)	0.5221 (4)	0.080 (3)
H5	0.4382	0.3365	0.5592	0.096*
C6	0.3359 (7)	0.3546 (13)	0.5022 (5)	0.081 (3)
H6	0.3129	0.4137	0.5271	0.098*
C7	0.2894 (7)	0.3223 (11)	0.4482 (5)	0.072 (3)
C8	0.3263 (6)	0.2311 (10)	0.4100 (4)	0.059 (2)
C9	0.2801 (6)	0.2008 (11)	0.3545 (4)	0.066 (2)
H9	0.3017	0.1398	0.3293	0.079*
C10	0.2047 (6)	0.2572 (12)	0.3361 (5)	0.080 (3)
H10	0.1768	0.2388	0.2985	0.096*
C11	0.1701 (7)	0.3416 (14)	0.3733 (6)	0.088 (3)
H11	0.1183	0.3770	0.3609	0.105*
C12	0.2101 (7)	0.3724 (12)	0.4265 (5)	0.076 (3)
H12	0.1853	0.4293	0.4506	0.091*
C13	0.3652 (3)	0.2728 (9)	0.1786 (3)	0.0301 (15)
C14	0.2921 (4)	0.3284 (9)	0.1342 (3)	0.0366 (16)
H14A	0.2846	0.4488	0.1390	0.044*
H14B	0.3009	0.3120	0.0966	0.044*
C15	0.2176 (4)	0.2374 (8)	0.1364 (3)	0.0357 (16)
C16	0.2114 (4)	0.1483 (9)	0.1830 (3)	0.0458 (18)
H16	0.2549	0.1389	0.2139	0.055*
C17	0.1408 (5)	0.0696 (10)	0.1858 (4)	0.063 (2)
H17	0.1381	0.0069	0.2179	0.075*
C18	0.0766 (5)	0.0864 (11)	0.1410 (4)	0.063 (2)
H18	0.0296	0.0376	0.1436	0.075*
C19	0.0788 (4)	0.1738 (11)	0.0917 (4)	0.056 (2)
C20	0.1505 (4)	0.2507 (9)	0.0887 (3)	0.0427 (18)
C21	0.1516 (4)	0.3357 (10)	0.0381 (3)	0.051 (2)
H21	0.1980	0.3864	0.0352	0.061*
C22	0.0872 (5)	0.3475 (12)	−0.0073 (4)	0.066 (2)
H22	0.0896	0.4057	−0.0403	0.079*
C23	0.0173 (5)	0.2690 (12)	−0.0027 (4)	0.077 (3)
H23	−0.0268	0.2749	−0.0333	0.092*
C24	0.0130 (5)	0.1872 (12)	0.0440 (4)	0.069 (3)
H24	−0.0341	0.1373	0.0456	0.082*
C25	0.6191 (4)	0.2342 (8)	0.2145 (3)	0.0319 (15)
C26	0.6633 (4)	0.1225 (9)	0.1826 (3)	0.0477 (19)
H26A	0.6296	0.0998	0.1449	0.057*
H26B	0.6737	0.0149	0.2025	0.057*
C27	0.7401 (4)	0.1926 (9)	0.1754 (3)	0.0455 (19)
C28	0.7411 (5)	0.2700 (10)	0.1254 (4)	0.053 (2)
H28	0.6943	0.2827	0.0976	0.063*
C29	0.8106 (5)	0.3315 (11)	0.1143 (4)	0.061 (2)
H29	0.8092	0.3841	0.0796	0.073*
C30	0.8794 (5)	0.3141 (10)	0.1539 (4)	0.059 (2)
H30	0.9253	0.3526	0.1458	0.071*
C31	0.8830 (4)	0.2387 (10)	0.2073 (4)	0.052 (2)
C32	0.8112 (4)	0.1781 (9)	0.2182 (3)	0.0488 (19)
C33	0.8159 (5)	0.1038 (10)	0.2716 (4)	0.058 (2)
H33	0.7704	0.0641	0.2800	0.069*
C34	0.8852 (6)	0.0884 (11)	0.3115 (4)	0.072 (3)
H34	0.8865	0.0377	0.3464	0.087*
C35	0.9549 (6)	0.1483 (12)	0.3005 (5)	0.078 (3)
H35	1.0021	0.1380	0.3280	0.094*
C36	0.9526 (5)	0.2211 (12)	0.2494 (4)	0.068 (2)
H36	0.9989	0.2605	0.2423	0.081*
C37	0.6886 (4)	0.3035 (9)	0.3681 (3)	0.0412 (17)
H37	0.7173	0.3518	0.3448	0.049*
C38	0.6820 (5)	0.2000 (12)	0.4591 (3)	0.067 (2)
H38A	0.6270	0.2052	0.4412	0.101*
H38B	0.6932	0.2654	0.4937	0.101*
H38C	0.6971	0.0841	0.4679	0.101*
C39	0.8097 (4)	0.2947 (11)	0.4423 (4)	0.067 (2)
H39A	0.8311	0.3311	0.4115	0.100*
H39B	0.8343	0.1906	0.4579	0.100*
H39C	0.8191	0.3801	0.4715	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Tb1	0.02147 (16)	0.02162 (17)	0.02753 (16)	−0.00010 (14)	0.00560 (11)	−0.00052 (14)
N1	0.039 (4)	0.049 (4)	0.046 (4)	0.000 (3)	−0.001 (3)	−0.005 (3)
O1	0.035 (3)	0.035 (3)	0.034 (2)	0.000 (2)	0.013 (2)	−0.002 (2)
O2	0.050 (3)	0.031 (3)	0.042 (3)	0.005 (2)	0.024 (2)	0.006 (2)
O3	0.029 (3)	0.037 (3)	0.042 (3)	0.001 (2)	−0.003 (2)	−0.006 (2)
O4	0.040 (3)	0.023 (3)	0.038 (3)	0.005 (2)	0.003 (2)	0.0023 (19)
O5	0.030 (2)	0.029 (3)	0.037 (2)	−0.0011 (19)	0.016 (2)	−0.003 (2)
O6	0.032 (3)	0.032 (3)	0.054 (3)	−0.005 (2)	0.018 (2)	−0.010 (2)
O7	0.034 (3)	0.038 (3)	0.054 (3)	−0.002 (2)	0.002 (2)	0.010 (2)
C1	0.038 (4)	0.034 (4)	0.039 (4)	0.003 (3)	0.017 (3)	0.004 (3)
C2	0.069 (5)	0.039 (4)	0.047 (4)	0.003 (4)	0.031 (4)	0.005 (4)
C3	0.084 (6)	0.041 (5)	0.056 (5)	−0.004 (4)	0.040 (5)	0.011 (4)
C4	0.097 (7)	0.053 (6)	0.060 (6)	0.000 (5)	0.039 (5)	0.004 (4)
C5	0.125 (10)	0.068 (7)	0.056 (6)	−0.007 (7)	0.040 (6)	0.003 (5)
C6	0.114 (9)	0.057 (6)	0.089 (8)	0.005 (6)	0.057 (7)	0.007 (6)
C7	0.098 (8)	0.047 (6)	0.087 (7)	−0.003 (5)	0.057 (6)	0.015 (5)
C8	0.082 (7)	0.040 (5)	0.073 (6)	−0.003 (4)	0.051 (5)	0.011 (4)
C9	0.079 (7)	0.049 (6)	0.082 (7)	0.000 (5)	0.041 (6)	0.011 (5)
C10	0.085 (8)	0.058 (6)	0.105 (8)	0.000 (6)	0.038 (6)	0.010 (6)
C11	0.089 (8)	0.065 (7)	0.121 (10)	0.001 (6)	0.049 (8)	0.018 (7)
C12	0.091 (8)	0.055 (6)	0.103 (8)	0.007 (5)	0.064 (7)	0.009 (6)
C13	0.020 (3)	0.036 (4)	0.034 (4)	−0.002 (3)	0.006 (3)	0.007 (3)
C14	0.032 (4)	0.029 (4)	0.044 (4)	−0.002 (3)	0.002 (3)	0.006 (3)
C15	0.029 (4)	0.028 (4)	0.050 (4)	0.003 (3)	0.012 (3)	0.000 (3)
C16	0.037 (4)	0.041 (4)	0.061 (5)	0.006 (3)	0.015 (4)	0.004 (4)
C17	0.056 (6)	0.051 (5)	0.087 (6)	−0.005 (4)	0.031 (5)	0.008 (5)
C18	0.038 (5)	0.055 (6)	0.098 (7)	−0.003 (4)	0.021 (5)	−0.004 (5)
C19	0.034 (5)	0.050 (5)	0.081 (6)	0.004 (4)	0.010 (4)	−0.012 (5)
C20	0.030 (4)	0.033 (4)	0.064 (5)	0.003 (3)	0.009 (3)	−0.009 (4)
C21	0.032 (4)	0.050 (5)	0.062 (5)	0.004 (4)	−0.004 (4)	−0.005 (4)
C22	0.046 (5)	0.074 (6)	0.068 (6)	0.010 (5)	−0.003 (4)	−0.003 (5)
C23	0.049 (6)	0.076 (7)	0.090 (7)	0.004 (5)	−0.012 (5)	−0.013 (6)
C24	0.038 (5)	0.063 (6)	0.097 (7)	−0.001 (4)	0.001 (5)	−0.009 (6)
C25	0.032 (4)	0.026 (4)	0.043 (4)	0.001 (3)	0.019 (3)	0.001 (3)
C26	0.040 (4)	0.038 (4)	0.073 (5)	−0.004 (3)	0.029 (4)	−0.015 (4)
C27	0.042 (4)	0.035 (4)	0.067 (5)	−0.005 (3)	0.029 (4)	−0.016 (4)
C28	0.052 (5)	0.049 (5)	0.066 (5)	−0.004 (4)	0.029 (4)	−0.011 (4)
C29	0.068 (6)	0.053 (6)	0.070 (6)	−0.007 (5)	0.034 (5)	−0.011 (5)
C30	0.057 (6)	0.052 (6)	0.081 (6)	−0.013 (4)	0.042 (5)	−0.014 (5)
C31	0.044 (5)	0.040 (5)	0.080 (6)	−0.003 (4)	0.030 (4)	−0.014 (4)
C32	0.048 (5)	0.033 (4)	0.073 (5)	−0.001 (4)	0.029 (4)	−0.011 (4)
C33	0.058 (6)	0.040 (5)	0.081 (6)	−0.002 (4)	0.028 (5)	−0.002 (4)
C34	0.079 (7)	0.050 (6)	0.087 (7)	−0.001 (5)	0.018 (6)	0.007 (5)
C35	0.064 (7)	0.059 (6)	0.105 (8)	0.007 (5)	0.009 (6)	−0.006 (6)
C36	0.055 (6)	0.055 (6)	0.096 (7)	0.000 (4)	0.025 (5)	−0.011 (5)
C37	0.038 (4)	0.031 (4)	0.052 (5)	−0.002 (3)	0.006 (4)	0.000 (3)
C38	0.070 (6)	0.082 (7)	0.047 (5)	0.015 (5)	0.008 (4)	0.002 (5)
C39	0.032 (4)	0.069 (6)	0.086 (6)	−0.002 (4)	−0.013 (4)	−0.005 (5)

Geometric parameters (Å, º) top

Tb1—O4ⁱ	2.322 (4)	C15—C16	1.357 (9)
Tb1—O3	2.341 (4)	C15—C20	1.433 (9)
Tb1—O1ⁱ	2.348 (4)	C16—C17	1.409 (10)
Tb1—O2	2.407 (4)	C16—H16	0.9300
Tb1—O7	2.427 (4)	C17—C18	1.363 (12)
Tb1—O5ⁱ	2.473 (4)	C17—H17	0.9300
Tb1—O5	2.474 (4)	C18—C19	1.387 (11)
Tb1—O6	2.542 (4)	C18—H18	0.9300
Tb1—O1	2.677 (4)	C19—C24	1.420 (10)
N1—C37	1.307 (8)	C19—C20	1.421 (10)
N1—C38	1.442 (9)	C20—C21	1.399 (10)
N1—C39	1.465 (8)	C21—C22	1.370 (10)
O1—C1	1.265 (7)	C21—H21	0.9300
O1—Tb1ⁱⁱ	2.348 (4)	C22—C23	1.410 (12)
O2—C1	1.240 (8)	C22—H22	0.9300
O3—C13	1.256 (7)	C23—C24	1.319 (12)
O4—C13	1.252 (7)	C23—H23	0.9300
O4—Tb1ⁱⁱ	2.322 (4)	C24—H24	0.9300
O5—C25	1.287 (7)	C25—C26	1.510 (9)
O5—Tb1ⁱⁱ	2.473 (4)	C26—C27	1.514 (9)
O6—C25	1.239 (7)	C26—H26A	0.9700
O7—C37	1.234 (7)	C26—H26B	0.9700
C1—C2	1.509 (9)	C27—C28	1.359 (10)
C2—C3	1.517 (10)	C27—C32	1.416 (10)
C2—H2A	0.9700	C28—C29	1.406 (10)
C2—H2B	0.9700	C28—H28	0.9300
C3—C4	1.377 (11)	C29—C30	1.351 (11)
C3—C8	1.413 (11)	C29—H29	0.9300
C4—C5	1.462 (12)	C30—C31	1.408 (11)
C4—H4	0.9300	C30—H30	0.9300
C5—C6	1.335 (13)	C31—C36	1.391 (11)
C5—H5	0.9300	C31—C32	1.439 (10)
C6—C7	1.379 (13)	C32—C33	1.403 (10)
C6—H6	0.9300	C33—C34	1.358 (12)
C7—C12	1.422 (13)	C33—H33	0.9300
C7—C8	1.449 (11)	C34—C35	1.404 (12)
C8—C9	1.404 (12)	C34—H34	0.9300
C9—C10	1.367 (12)	C35—C36	1.353 (12)
C9—H9	0.9300	C35—H35	0.9300
C10—C11	1.379 (13)	C36—H36	0.9300
C10—H10	0.9300	C37—H37	0.9300
C11—C12	1.324 (13)	C38—H38A	0.9600
C11—H11	0.9300	C38—H38B	0.9600
C12—H12	0.9300	C38—H38C	0.9600
C13—C14	1.520 (8)	C39—H39A	0.9600
C14—C15	1.509 (9)	C39—H39B	0.9600
C14—H14A	0.9700	C39—H39C	0.9600
C14—H14B	0.9700

O4ⁱ—Tb1—O3	146.45 (15)	O3—C13—C14	116.9 (6)
O4ⁱ—Tb1—O1ⁱ	81.07 (15)	C15—C14—C13	115.5 (5)
O3—Tb1—O1ⁱ	79.23 (15)	C15—C14—H14A	108.4
O4ⁱ—Tb1—O2	96.39 (16)	C13—C14—H14A	108.4
O3—Tb1—O2	84.51 (16)	C15—C14—H14B	108.4
O1ⁱ—Tb1—O2	144.54 (15)	C13—C14—H14B	108.4
O4ⁱ—Tb1—O7	71.57 (16)	H14A—C14—H14B	107.5
O3—Tb1—O7	137.93 (16)	C16—C15—C20	118.9 (6)
O1ⁱ—Tb1—O7	139.27 (15)	C16—C15—C14	121.9 (6)
O2—Tb1—O7	69.87 (15)	C20—C15—C14	119.2 (6)
O4ⁱ—Tb1—O5ⁱ	72.48 (14)	C15—C16—C17	121.8 (7)
O3—Tb1—O5ⁱ	75.20 (14)	C15—C16—H16	119.1
O1ⁱ—Tb1—O5ⁱ	69.06 (14)	C17—C16—H16	119.1
O2—Tb1—O5ⁱ	76.42 (14)	C18—C17—C16	119.1 (8)
O7—Tb1—O5ⁱ	126.59 (15)	C18—C17—H17	120.4
O4ⁱ—Tb1—O5	128.86 (14)	C16—C17—H17	120.4
O3—Tb1—O5	79.33 (14)	C17—C18—C19	122.3 (8)
O1ⁱ—Tb1—O5	93.34 (14)	C17—C18—H18	118.9
O2—Tb1—O5	114.40 (15)	C19—C18—H18	118.9
O7—Tb1—O5	81.68 (15)	C18—C19—C24	122.8 (8)
O5ⁱ—Tb1—O5	151.24 (3)	C18—C19—C20	118.4 (7)
O4ⁱ—Tb1—O6	78.16 (15)	C24—C19—C20	118.9 (8)
O3—Tb1—O6	121.00 (15)	C21—C20—C19	117.3 (7)
O1ⁱ—Tb1—O6	73.50 (14)	C21—C20—C15	123.2 (6)
O2—Tb1—O6	140.97 (15)	C19—C20—C15	119.6 (7)
O7—Tb1—O6	71.80 (15)	C22—C21—C20	122.8 (8)
O5ⁱ—Tb1—O6	135.12 (14)	C22—C21—H21	118.6
O5—Tb1—O6	51.96 (13)	C20—C21—H21	118.6
O4ⁱ—Tb1—O1	132.16 (14)	C21—C22—C23	118.2 (9)
O3—Tb1—O1	72.78 (14)	C21—C22—H22	120.9
O1ⁱ—Tb1—O1	146.51 (8)	C23—C22—H22	120.9
O2—Tb1—O1	50.50 (14)	C24—C23—C22	121.6 (9)
O7—Tb1—O1	65.16 (14)	C24—C23—H23	119.2
O5ⁱ—Tb1—O1	119.23 (13)	C22—C23—H23	119.2
O5—Tb1—O1	63.99 (13)	C23—C24—C19	121.3 (9)
O6—Tb1—O1	105.65 (13)	C23—C24—H24	119.3
C37—N1—C38	119.6 (6)	C19—C24—H24	119.3
C37—N1—C39	121.6 (7)	O6—C25—O5	121.0 (6)
C38—N1—C39	118.9 (6)	O6—C25—C26	122.6 (6)
C1—O1—Tb1ⁱⁱ	161.5 (4)	O5—C25—C26	116.4 (6)
C1—O1—Tb1	87.1 (4)	C25—C26—C27	116.0 (6)
Tb1ⁱⁱ—O1—Tb1	110.33 (15)	C25—C26—H26A	108.3
C1—O2—Tb1	100.5 (4)	C27—C26—H26A	108.3
C13—O3—Tb1	137.3 (4)	C25—C26—H26B	108.3
C13—O4—Tb1ⁱⁱ	139.8 (4)	C27—C26—H26B	108.3
C25—O5—Tb1ⁱⁱ	141.8 (4)	H26A—C26—H26B	107.4
C25—O5—Tb1	94.5 (4)	C28—C27—C32	118.6 (7)
Tb1ⁱⁱ—O5—Tb1	113.12 (15)	C28—C27—C26	118.7 (7)
C25—O6—Tb1	92.5 (4)	C32—C27—C26	122.7 (7)
C37—O7—Tb1	130.1 (4)	C27—C28—C29	122.3 (8)
O2—C1—O1	121.1 (6)	C27—C28—H28	118.9
O2—C1—C2	120.7 (6)	C29—C28—H28	118.9
O1—C1—C2	118.0 (6)	C30—C29—C28	120.0 (8)
C1—C2—C3	113.6 (6)	C30—C29—H29	120.0
C1—C2—H2A	108.8	C28—C29—H29	120.0
C3—C2—H2A	108.8	C29—C30—C31	121.2 (7)
C1—C2—H2B	108.8	C29—C30—H30	119.4
C3—C2—H2B	108.8	C31—C30—H30	119.4
H2A—C2—H2B	107.7	C36—C31—C30	122.7 (8)
C4—C3—C8	121.0 (8)	C36—C31—C32	119.2 (8)
C4—C3—C2	119.3 (8)	C30—C31—C32	118.0 (8)
C8—C3—C2	119.7 (8)	C33—C32—C27	122.8 (7)
C3—C4—C5	118.9 (9)	C33—C32—C31	117.2 (8)
C3—C4—H4	120.5	C27—C32—C31	119.9 (7)
C5—C4—H4	120.5	C34—C33—C32	121.6 (8)
C6—C5—C4	118.1 (9)	C34—C33—H33	119.2
C6—C5—H5	120.9	C32—C33—H33	119.2
C4—C5—H5	120.9	C33—C34—C35	120.7 (9)
C5—C6—C7	126.1 (10)	C33—C34—H34	119.6
C5—C6—H6	117.0	C35—C34—H34	119.6
C7—C6—H6	117.0	C36—C35—C34	119.3 (9)
C6—C7—C12	126.4 (10)	C36—C35—H35	120.4
C6—C7—C8	116.1 (10)	C34—C35—H35	120.4
C12—C7—C8	117.5 (10)	C35—C36—C31	121.9 (9)
C9—C8—C3	123.7 (8)	C35—C36—H36	119.1
C9—C8—C7	116.6 (9)	C31—C36—H36	119.1
C3—C8—C7	119.7 (9)	O7—C37—N1	123.9 (7)
C10—C9—C8	122.7 (9)	O7—C37—H37	118.0
C10—C9—H9	118.7	N1—C37—H37	118.0
C8—C9—H9	118.7	N1—C38—H38A	109.5
C9—C10—C11	119.9 (11)	N1—C38—H38B	109.5
C9—C10—H10	120.0	H38A—C38—H38B	109.5
C11—C10—H10	120.0	N1—C38—H38C	109.5
C12—C11—C10	120.4 (11)	H38A—C38—H38C	109.5
C12—C11—H11	119.8	H38B—C38—H38C	109.5
C10—C11—H11	119.8	N1—C39—H39A	109.5
C11—C12—C7	122.9 (10)	N1—C39—H39B	109.5
C11—C12—H12	118.6	H39A—C39—H39B	109.5
C7—C12—H12	118.6	N1—C39—H39C	109.5
O4—C13—O3	126.7 (6)	H39A—C39—H39C	109.5
O4—C13—C14	116.3 (6)	H39B—C39—H39C	109.5

O4ⁱ—Tb1—O1—C1	51.7 (4)	C5—C6—C7—C8	−0.3 (15)
O3—Tb1—O1—C1	−102.0 (4)	C4—C3—C8—C9	178.9 (8)
O1ⁱ—Tb1—O1—C1	−136.6 (4)	C2—C3—C8—C9	0.3 (11)
O2—Tb1—O1—C1	−4.7 (4)	C4—C3—C8—C7	−0.6 (12)
O7—Tb1—O1—C1	79.0 (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—C1	171.7 (4)	C12—C7—C8—C9	0.2 (11)
O6—Tb1—O1—C1	139.8 (4)	C6—C7—C8—C3	0.9 (12)
O4ⁱ—Tb1—O1—Tb1ⁱⁱ	−134.69 (18)	C12—C7—C8—C3	179.8 (7)
O3—Tb1—O1—Tb1ⁱⁱ	71.61 (18)	C3—C8—C9—C10	−177.8 (8)
O1ⁱ—Tb1—O1—Tb1ⁱⁱ	37.0 (2)	C7—C8—C9—C10	1.7 (12)
O2—Tb1—O1—Tb1ⁱⁱ	168.8 (3)	C8—C9—C10—C11	−2.8 (14)
O7—Tb1—O1—Tb1ⁱⁱ	−107.5 (2)	C9—C10—C11—C12	1.8 (15)
O5ⁱ—Tb1—O1—Tb1ⁱⁱ	132.94 (15)	C10—C11—C12—C7	0.1 (16)
O5—Tb1—O1—Tb1ⁱⁱ	−14.70 (14)	C6—C7—C12—C11	177.6 (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—O3	13.1 (11)
O3—Tb1—O2—C1	77.1 (4)	Tb1ⁱⁱ—O4—C13—C14	−169.7 (4)
O1ⁱ—Tb1—O2—C1	139.8 (4)	Tb1—O3—C13—O4	19.4 (10)
O7—Tb1—O2—C1	−69.0 (4)	Tb1—O3—C13—C14	−157.8 (4)
O5ⁱ—Tb1—O2—C1	153.2 (4)	O4—C13—C14—C15	63.9 (8)
O5—Tb1—O2—C1	1.4 (4)	O3—C13—C14—C15	−118.6 (6)
O6—Tb1—O2—C1	−57.6 (5)	C13—C14—C15—C16	17.4 (10)
O1—Tb1—O2—C1	4.9 (4)	C13—C14—C15—C20	−165.0 (6)
O4ⁱ—Tb1—O3—C13	160.7 (5)	C20—C15—C16—C17	−0.3 (11)
O1ⁱ—Tb1—O3—C13	105.6 (6)	C14—C15—C16—C17	177.2 (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—C19	2.2 (13)
O5ⁱ—Tb1—O3—C13	176.6 (6)	C17—C18—C19—C24	177.7 (8)
O5—Tb1—O3—C13	10.1 (6)	C17—C18—C19—C20	−1.2 (12)
O6—Tb1—O3—C13	42.5 (6)	C18—C19—C20—C21	179.0 (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—C25	145.3 (4)	C24—C19—C20—C15	−179.6 (7)
O1ⁱ—Tb1—O5—C25	66.9 (4)	C16—C15—C20—C21	−178.2 (7)
O2—Tb1—O5—C25	−135.8 (3)	C14—C15—C20—C21	4.2 (10)
O7—Tb1—O5—C25	−72.4 (4)	C16—C15—C20—C19	1.3 (10)
O5ⁱ—Tb1—O5—C25	117.3 (3)	C14—C15—C20—C19	−176.3 (6)
O6—Tb1—O5—C25	0.9 (3)	C19—C20—C21—C22	0.3 (11)
O1—Tb1—O5—C25	−138.8 (4)	C15—C20—C21—C22	179.8 (7)
O4ⁱ—Tb1—O5—Tb1ⁱⁱ	138.69 (17)	C20—C21—C22—C23	−0.6 (13)
O3—Tb1—O5—Tb1ⁱⁱ	−61.71 (17)	C21—C22—C23—C24	0.6 (14)
O1ⁱ—Tb1—O5—Tb1ⁱⁱ	−140.09 (17)	C22—C23—C24—C19	−0.3 (15)
O2—Tb1—O5—Tb1ⁱⁱ	17.2 (2)	C18—C19—C24—C23	−178.9 (9)
O7—Tb1—O5—Tb1ⁱⁱ	80.57 (18)	C20—C19—C24—C23	0.1 (13)
O5ⁱ—Tb1—O5—Tb1ⁱⁱ	−89.7 (3)	Tb1—O6—C25—O5	1.7 (6)
O6—Tb1—O5—Tb1ⁱⁱ	153.9 (3)	Tb1—O6—C25—C26	179.9 (6)
O1—Tb1—O5—Tb1ⁱⁱ	14.21 (14)	Tb1ⁱⁱ—O5—C25—O6	−139.3 (5)
O4ⁱ—Tb1—O6—C25	166.9 (4)	Tb1—O5—C25—O6	−1.8 (6)
O3—Tb1—O6—C25	−42.9 (4)	Tb1ⁱⁱ—O5—C25—C26	42.5 (9)
O1ⁱ—Tb1—O6—C25	−109.0 (4)	Tb1—O5—C25—C26	179.9 (5)
O2—Tb1—O6—C25	81.4 (4)	O6—C25—C26—C27	−5.8 (11)
O7—Tb1—O6—C25	92.7 (4)	O5—C25—C26—C27	172.4 (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—C32	83.4 (9)
O1—Tb1—O6—C25	36.1 (4)	C32—C27—C28—C29	1.8 (11)
O4ⁱ—Tb1—O7—C37	−34.6 (6)	C26—C27—C28—C29	−177.0 (7)
O3—Tb1—O7—C37	165.0 (5)	C27—C28—C29—C30	0.2 (12)
O1ⁱ—Tb1—O7—C37	15.7 (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—C32	0.9 (12)
O5—Tb1—O7—C37	101.2 (6)	C28—C27—C32—C33	178.6 (7)
O6—Tb1—O7—C37	48.6 (6)	C26—C27—C32—C33	−2.6 (11)
O1—Tb1—O7—C37	166.3 (6)	C28—C27—C32—C31	−2.5 (11)
Tb1—O2—C1—O1	−9.4 (7)	C26—C27—C32—C31	176.3 (6)
Tb1—O2—C1—C2	166.5 (5)	C36—C31—C32—C33	0.1 (11)
Tb1ⁱⁱ—O1—C1—O2	−152.4 (10)	C30—C31—C32—C33	−179.8 (7)
Tb1—O1—C1—O2	8.3 (6)	C36—C31—C32—C27	−179.0 (7)
Tb1ⁱⁱ—O1—C1—C2	31.6 (17)	C30—C31—C32—C27	1.1 (11)
Tb1—O1—C1—C2	−167.7 (6)	C27—C32—C33—C34	178.6 (8)
O2—C1—C2—C3	20.5 (10)	C31—C32—C33—C34	−0.4 (11)
O1—C1—C2—C3	−163.4 (7)	C32—C33—C34—C35	0.5 (13)
C1—C2—C3—C4	−106.7 (8)	C33—C34—C35—C36	−0.4 (14)
C1—C2—C3—C8	72.0 (9)	C34—C35—C36—C31	0.1 (14)
C8—C3—C4—C5	−0.3 (12)	C30—C31—C36—C35	180.0 (8)
C2—C3—C4—C5	178.4 (7)	C32—C31—C36—C35	0.1 (13)
C3—C4—C5—C6	0.8 (13)	Tb1—O7—C37—N1	149.8 (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—O7	177.2 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C37—H37···O6	0.93	2.58	3.098 (8)	116
C38—H38A···O7	0.96	2.30	2.718 (9)	105
C17—H17···Cg1ⁱⁱ	0.93	2.81	3.534 (9)	135
C39—H39A···Cg2ⁱ	0.96	2.93	3.670 (10)	135

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

Experimental details

Crystal data
Chemical formula	[Tb(C₁₂H₉O₂)₃(C₃H₇NO)]
M_r	787.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	17.6484 (18), 7.8854 (10), 24.184 (3)
β (°)	104.613 (2)
V (Å³)	3256.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.23
Crystal size (mm)	0.32 × 0.17 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.536, 0.808
No. of measured, independent and observed [I > 2σ(I)] reflections	15719, 5733, 4274
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.106, 1.02
No. of reflections	5733
No. of parameters	435
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.17, −1.59

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Tb1—O4ⁱ	2.322 (4)	Tb1—O5ⁱ	2.473 (4)
Tb1—O3	2.341 (4)	Tb1—O5	2.474 (4)
Tb1—O1ⁱ	2.348 (4)	Tb1—O6	2.542 (4)
Tb1—O2	2.407 (4)	Tb1—O1	2.677 (4)
Tb1—O7	2.427 (4)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C37—H37···O6	0.93	2.58	3.098 (8)	115.5
C38—H38A···O7	0.96	2.30	2.718 (9)	105.3
C17—H17···Cg1ⁱⁱ	0.93	2.81	3.534 (9)	135
C39—H39A···Cg2ⁱ	0.96	2.93	3.670 (10)	135

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

Acknowledgements

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

References

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens. (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007a). Acta Cryst. E63, m2624. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007b). Acta Cryst. E63, m2797–m2798. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 12| December 2008| Page m1521

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