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

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ISSN: 2056-9890

Bis[4,4,5,5-tetra­methyl-2-(pyridin-2-yl-κ2N)imidazoline-1-oxyl 3-oxide-κO]tris­­(nitrato-κ2O,O′)terbium(III)

aChemical Institute, Linyi University, Linyi Shandong 276005, People's Republic of China
*Correspondence e-mail: lidongjiao@lyu.edu.cn

(Received 16 July 2012; accepted 23 September 2012; online 10 October 2012)

The title compound, [Tb(NO3)3(C12H16N3O2)2], was prepared from the nitroxide radical ligand 4,4,5,5-tetra­methyl­-2-(pyridin-2-yl)-imidazoline-1-oxyl-3-oxide and TbIII nitrate. The TbIII ion adopts a doubly-capped square-anti­prismatic coord­ination environment defined by three chelating nitrate anions and two N,O-bidentate nitronyl nitroxide radical ligands. Weak C—H⋯O hydrogen bonds connect the molecules into a three-dimensional framework. The title structure is isotypic with the Ho analogue [Li (2012[Li, D.-J. (2012). Acta Cryst. E68, m550.]). Acta Cryst. E68, 550].

Related literature

For background to the use of rare earth complexes with nitroxide radicals in coordination chemistry, see: Sutter et al. (1998[Sutter, J. P., Kahn, M. L. & Golhen, S. (1998). Chem. Eur. J. 4, 571-576.]); Kahn et al. (2000[Kahn, M. L., Sutter, J. P. & Golhen, S. (2000). J. Am. Chem. Soc. 122, 3413-3421.]); Lescop et al. (2000[Lescop, C., Luneau, D. & Bussière, G. (2000). Inorg. Chem. 39, 3740-3741.]). For the structures of related complexes, see: Li et al. (2004a[Li, D.-J., Liao, D.-Z. & Li, L.-C. (2004a). J. Coord. Chem. 57, 1571-1576.],b[Li, D.-J., Yan, S.-P. & Liao, D.-Z. (2004b). J. Mol. Struct. 698, 103-107.], 2005[Li, D.-J., Liao, D.-Z. & Li, L.-C. (2005). Chin. J. Struct. Chem. 24, 905-908.]); Li (2012[Li, D.-J. (2012). Acta Cryst. E68, m550.]).

[Scheme 1]

Experimental

Crystal data
  • [Tb(NO3)3(C12H16N3O2)2]

  • Mr = 813.51

  • Monoclinic, P 21 /n

  • a = 12.292 (3) Å

  • b = 11.114 (2) Å

  • c = 23.264 (5) Å

  • β = 98.37 (3)°

  • V = 3144.6 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.33 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.581, Tmax = 1.000

  • 25443 measured reflections

  • 5554 independent reflections

  • 4726 reflections with I > 2σ(I)

  • Rint = 0.059

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.071

  • S = 1.01

  • 5554 reflections

  • 432 parameters

  • H-atom parameters constrained

  • Δρmax = 0.89 e Å−3

  • Δρmin = −0.95 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C22—H22⋯O13i 0.93 2.55 3.440 (5) 161
C17—H17B⋯O6ii 0.96 2.40 3.327 (5) 161
C6—H6B⋯O3iii 0.96 2.55 3.473 (5) 161
C24—H24⋯O9iv 0.93 2.38 3.211 (5) 148
Symmetry codes: (i) [-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y+1, -z; (iii) -x+1, -y+2, -z; (iv) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supporting information


Comment top

As a continuation of our work on complexes containing nitroxide radicals as the ligand, the title Tb complex is reported. An ORTEP drawing of [TbIII(NIT2Py)2(NO3)3] is illustrated in Fig. 1. The TbIII ion is ten-coordinated by three η2-nitrato anions and two NIT2Py radicals which bind via one oxygen atom of the nitronyl nitroxide moiety and one nitrogen atom of the pyridine substituent. The complex is further connected by weak C—H···O H-bonds into a three-dimensional framework as shown in Fig. 2.

Related literature top

For background to the use of rare earth complexes with nitroxide radicals in coordination chemistry, see: Sutter et al. (1998); Kahn et al. (2000); Lescop et al. (2000). For the structures of related complexes, see: Li et al. (2004a,b, 2005); Li (2012).

Experimental top

The compound was synthesized by the following procedure. Tb(NO3)3.6H2O (0.045 g, 0.2 mmol) and NIT2Py (0.047 g, 0.2 mmol) were dissolved in 10 mL of anhydrous THF. The mixture was stirred at room temperature for four hours and then filtered. The dark brown filtrate was allowed to stand in the dark for one week. Dark brown crystals were obtained.

Refinement top

Hydrogen atoms were placed in calculated positions (C—H = 0.93–0.96 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(Caromatic) and 1.5Ueq(Cmethyl).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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 the title compound drawn with 30% ellipsoidal probability.
[Figure 2] Fig. 2. The three-dimensional framework of the structure connected through intermolecular hydrogen bonds.
Bis[4,4,5,5-tetramethyl-2-(pyridin-2-yl-κ2N)imidazoline-1-oxyl 3-oxide-κO]tris(nitrato-κ2O,O')terbium(III) top
Crystal data top
[Tb(NO3)3(C12H16N3O2)2]F(000) = 1632
Mr = 813.51Dx = 1.718 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9251 reflections
a = 12.292 (3) Åθ = 3.0–27.9°
b = 11.114 (2) ŵ = 2.33 mm1
c = 23.264 (5) ÅT = 293 K
β = 98.37 (3)°Prism, colorless
V = 3144.6 (11) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
5554 independent reflections
Radiation source: fine-focus sealed tube4726 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ωθ scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1414
Tmin = 0.581, Tmax = 1.000k = 1313
25443 measured reflectionsl = 2727
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0354P)2]
where P = (Fo2 + 2Fc2)/3
5554 reflections(Δ/σ)max = 0.001
432 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = 0.95 e Å3
Crystal data top
[Tb(NO3)3(C12H16N3O2)2]V = 3144.6 (11) Å3
Mr = 813.51Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.292 (3) ŵ = 2.33 mm1
b = 11.114 (2) ÅT = 293 K
c = 23.264 (5) Å0.20 × 0.20 × 0.20 mm
β = 98.37 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
5554 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
4726 reflections with I > 2σ(I)
Tmin = 0.581, Tmax = 1.000Rint = 0.059
25443 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.071H-atom parameters constrained
S = 1.01Δρmax = 0.89 e Å3
5554 reflectionsΔρmin = 0.95 e Å3
432 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Tb10.179699 (13)0.838779 (16)0.103896 (7)0.02337 (7)
C10.5499 (3)1.0194 (4)0.21909 (17)0.0512 (12)
H1A0.52851.09050.23810.077*
H1B0.62861.01430.22390.077*
H1C0.52090.94970.23600.077*
C20.5046 (3)1.0251 (4)0.15437 (16)0.0342 (9)
C30.5415 (3)0.9164 (4)0.12280 (18)0.0470 (11)
H3A0.52850.84460.14370.071*
H3B0.61860.92320.12040.071*
H3C0.50090.91270.08430.071*
C40.6215 (3)1.2196 (5)0.1523 (2)0.0620 (14)
H4A0.62081.29730.13420.093*
H4B0.68691.17710.14620.093*
H4C0.62041.22920.19320.093*
C50.5205 (3)1.1483 (4)0.12557 (18)0.0366 (10)
C60.5140 (3)1.1439 (4)0.05979 (18)0.0506 (12)
H6A0.44851.10200.04340.076*
H6B0.57721.10260.04980.076*
H6C0.51221.22440.04470.076*
C70.3375 (3)1.1328 (3)0.14343 (15)0.0273 (8)
C80.2205 (3)1.1605 (3)0.13872 (15)0.0264 (8)
C90.1869 (3)1.2733 (4)0.15514 (17)0.0392 (10)
H90.23751.32870.17310.047*
C100.0755 (3)1.3009 (4)0.1439 (2)0.0516 (12)
H100.04981.37520.15460.062*
C110.0038 (4)1.2166 (4)0.11684 (19)0.0496 (12)
H110.07071.23410.10750.060*
C120.0440 (3)1.1056 (4)0.10369 (16)0.0342 (9)
H120.00541.04890.08580.041*
C130.0898 (3)0.5854 (4)0.02645 (19)0.0527 (13)
H13A0.04900.62570.00000.079*
H13B0.13570.52470.00600.079*
H13C0.03970.54850.05690.079*
C140.2299 (3)0.7483 (4)0.00525 (17)0.0502 (12)
H14A0.27480.80430.02270.075*
H14B0.27600.69490.02000.075*
H14C0.18240.79150.01680.075*
C150.1608 (3)0.6758 (3)0.05252 (15)0.0276 (8)
C160.2276 (3)0.6246 (3)0.09918 (16)0.0282 (8)
C170.3508 (3)0.6170 (4)0.08142 (19)0.0464 (11)
H17A0.38410.58530.11310.070*
H17B0.36680.56490.04830.070*
H17C0.37950.69580.07160.070*
C180.1832 (4)0.5038 (4)0.12504 (19)0.0554 (12)
H18A0.10540.51020.13730.083*
H18B0.19740.44200.09610.083*
H18C0.21910.48400.15780.083*
C190.1140 (3)0.7868 (3)0.13971 (14)0.0248 (8)
C200.0612 (3)0.8733 (3)0.18217 (15)0.0267 (8)
C210.1226 (3)0.9372 (4)0.21670 (16)0.0403 (10)
H210.19830.92630.21310.048*
C220.0699 (3)1.0181 (4)0.25706 (17)0.0482 (12)
H220.10991.06570.27940.058*
C230.0425 (3)1.0260 (4)0.26313 (17)0.0444 (11)
H230.08091.07500.29150.053*
C240.0971 (3)0.9599 (3)0.22643 (15)0.0325 (9)
H240.17320.96700.23060.039*
N10.4181 (2)1.2129 (3)0.13688 (14)0.0360 (8)
N20.3810 (2)1.0241 (3)0.15072 (12)0.0269 (7)
N30.1495 (2)1.0751 (3)0.11510 (12)0.0269 (7)
N40.2016 (2)0.7157 (3)0.14721 (12)0.0272 (7)
N50.0869 (2)0.7638 (3)0.08801 (11)0.0224 (6)
N60.0488 (2)0.8867 (3)0.18532 (12)0.0281 (7)
N70.2135 (2)0.9484 (3)0.00603 (13)0.0334 (8)
N80.2955 (3)0.6582 (3)0.04797 (18)0.0544 (11)
N90.1719 (3)0.6418 (3)0.18668 (15)0.0360 (8)
O10.4056 (3)1.3255 (3)0.12888 (16)0.0603 (9)
O20.33022 (18)0.9255 (2)0.16160 (10)0.0279 (6)
O30.2273 (2)0.9783 (3)0.05526 (11)0.0507 (8)
O40.29363 (19)0.9350 (2)0.03460 (11)0.0364 (7)
O50.11923 (18)0.9293 (3)0.00678 (10)0.0352 (6)
O60.3472 (3)0.5873 (4)0.02285 (18)0.1058 (16)
O70.3335 (2)0.7016 (3)0.09700 (13)0.0468 (8)
O80.1999 (2)0.6941 (3)0.02583 (13)0.0475 (8)
O90.1640 (2)0.5585 (3)0.22000 (13)0.0593 (9)
O100.2374 (2)0.7298 (3)0.19933 (11)0.0395 (7)
O110.1141 (2)0.6446 (2)0.13669 (12)0.0393 (7)
O120.00934 (19)0.8177 (2)0.06566 (10)0.0284 (6)
O130.2481 (2)0.7132 (3)0.19264 (11)0.0446 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Tb10.02218 (11)0.02498 (12)0.02300 (11)0.00103 (8)0.00341 (7)0.00178 (7)
C10.027 (2)0.080 (4)0.044 (3)0.002 (2)0.0055 (19)0.003 (2)
C20.0182 (18)0.048 (3)0.036 (2)0.0018 (18)0.0017 (16)0.0084 (19)
C30.035 (2)0.048 (3)0.058 (3)0.009 (2)0.008 (2)0.009 (2)
C40.032 (2)0.064 (4)0.089 (4)0.021 (2)0.008 (2)0.014 (3)
C50.024 (2)0.039 (3)0.046 (2)0.0066 (18)0.0044 (18)0.0090 (19)
C60.037 (2)0.072 (4)0.046 (3)0.002 (2)0.015 (2)0.003 (2)
C70.029 (2)0.025 (2)0.0274 (19)0.0000 (16)0.0047 (16)0.0067 (16)
C80.0275 (19)0.030 (2)0.0213 (18)0.0013 (17)0.0017 (15)0.0027 (16)
C90.039 (2)0.036 (3)0.041 (2)0.006 (2)0.0012 (19)0.0101 (19)
C100.044 (3)0.042 (3)0.068 (3)0.017 (2)0.006 (2)0.016 (2)
C110.037 (2)0.048 (3)0.063 (3)0.011 (2)0.002 (2)0.000 (2)
C120.032 (2)0.035 (2)0.035 (2)0.0023 (19)0.0012 (18)0.0041 (18)
C130.055 (3)0.047 (3)0.062 (3)0.014 (2)0.029 (2)0.029 (2)
C140.052 (3)0.058 (3)0.036 (2)0.016 (2)0.009 (2)0.011 (2)
C150.0285 (19)0.027 (2)0.028 (2)0.0079 (16)0.0075 (16)0.0056 (16)
C160.0277 (19)0.026 (2)0.032 (2)0.0048 (16)0.0066 (16)0.0013 (16)
C170.031 (2)0.060 (3)0.049 (3)0.008 (2)0.008 (2)0.017 (2)
C180.075 (3)0.037 (3)0.056 (3)0.001 (2)0.017 (3)0.009 (2)
C190.0203 (18)0.028 (2)0.0268 (19)0.0005 (16)0.0058 (15)0.0018 (16)
C200.0258 (19)0.027 (2)0.0267 (19)0.0001 (16)0.0033 (16)0.0018 (16)
C210.029 (2)0.053 (3)0.041 (2)0.001 (2)0.0114 (18)0.013 (2)
C220.050 (3)0.052 (3)0.046 (3)0.000 (2)0.018 (2)0.022 (2)
C230.052 (3)0.046 (3)0.036 (2)0.011 (2)0.008 (2)0.016 (2)
C240.030 (2)0.037 (2)0.030 (2)0.0058 (18)0.0021 (17)0.0068 (18)
N10.0300 (17)0.0256 (19)0.053 (2)0.0054 (15)0.0079 (16)0.0078 (16)
N20.0204 (15)0.033 (2)0.0263 (16)0.0030 (14)0.0013 (13)0.0074 (14)
N30.0245 (15)0.0304 (19)0.0256 (16)0.0010 (14)0.0025 (13)0.0008 (14)
N40.0262 (16)0.0329 (19)0.0233 (16)0.0043 (14)0.0068 (13)0.0005 (14)
N50.0195 (14)0.0236 (17)0.0245 (15)0.0018 (13)0.0046 (12)0.0007 (13)
N60.0255 (16)0.0309 (18)0.0274 (16)0.0010 (14)0.0025 (13)0.0003 (14)
N70.0307 (18)0.041 (2)0.0296 (18)0.0005 (15)0.0072 (15)0.0003 (15)
N80.054 (3)0.044 (3)0.068 (3)0.000 (2)0.019 (2)0.018 (2)
N90.0303 (18)0.038 (2)0.041 (2)0.0093 (16)0.0062 (16)0.0095 (17)
O10.057 (2)0.0310 (19)0.095 (3)0.0057 (15)0.0164 (19)0.0009 (17)
O20.0255 (13)0.0275 (15)0.0287 (13)0.0003 (12)0.0025 (11)0.0024 (11)
O30.0464 (17)0.078 (2)0.0306 (15)0.0007 (16)0.0160 (13)0.0132 (15)
O40.0244 (13)0.0506 (19)0.0336 (15)0.0066 (13)0.0023 (12)0.0005 (13)
O50.0211 (13)0.0544 (19)0.0299 (14)0.0065 (13)0.0032 (11)0.0036 (13)
O60.086 (3)0.106 (4)0.126 (4)0.028 (3)0.020 (3)0.078 (3)
O70.0440 (17)0.0422 (18)0.0526 (19)0.0099 (14)0.0009 (15)0.0186 (15)
O80.0453 (18)0.0449 (19)0.0511 (19)0.0009 (15)0.0031 (15)0.0186 (15)
O90.060 (2)0.056 (2)0.061 (2)0.0014 (17)0.0051 (16)0.0338 (18)
O100.0340 (15)0.0411 (19)0.0404 (16)0.0008 (14)0.0043 (13)0.0035 (14)
O110.0405 (16)0.0327 (17)0.0417 (17)0.0021 (13)0.0035 (14)0.0055 (13)
O120.0236 (13)0.0353 (16)0.0272 (13)0.0062 (11)0.0071 (11)0.0011 (11)
O130.0435 (16)0.061 (2)0.0340 (16)0.0152 (15)0.0210 (13)0.0046 (14)
Geometric parameters (Å, º) top
Tb1—O22.331 (2)C13—H13B0.9600
Tb1—O122.376 (2)C13—H13C0.9600
Tb1—O72.452 (3)C14—C151.519 (5)
Tb1—O112.463 (3)C14—H14A0.9600
Tb1—O82.465 (3)C14—H14B0.9600
Tb1—O52.486 (2)C14—H14C0.9600
Tb1—O42.522 (2)C15—N51.499 (4)
Tb1—O102.538 (3)C15—C161.561 (5)
Tb1—N32.671 (3)C16—N41.507 (5)
Tb1—N62.711 (3)C16—C171.513 (5)
C1—C21.529 (5)C16—C181.538 (5)
C1—H1A0.9600C17—H17A0.9600
C1—H1B0.9600C17—H17B0.9600
C1—H1C0.9600C17—H17C0.9600
C2—N21.509 (4)C18—H18A0.9600
C2—C31.518 (5)C18—H18B0.9600
C2—C51.549 (5)C18—H18C0.9600
C3—H3A0.9600C19—N51.319 (4)
C3—H3B0.9600C19—N41.367 (4)
C3—H3C0.9600C19—C201.461 (5)
C4—C51.527 (5)C20—N61.352 (4)
C4—H4A0.9600C20—C211.376 (5)
C4—H4B0.9600C21—C221.390 (5)
C4—H4C0.9600C21—H210.9300
C5—N11.505 (5)C22—C231.371 (5)
C5—C61.521 (5)C22—H220.9300
C6—H6A0.9600C23—C241.373 (5)
C6—H6B0.9600C23—H230.9300
C6—H6C0.9600C24—N61.328 (4)
C7—N21.321 (4)C24—H240.9300
C7—N11.358 (5)N1—O11.271 (4)
C7—C81.459 (5)N2—O21.305 (4)
C8—N31.351 (4)N4—O131.273 (3)
C8—C91.391 (5)N5—O121.297 (3)
C9—C101.392 (5)N7—O31.228 (4)
C9—H90.9300N7—O51.256 (3)
C10—C111.375 (6)N7—O41.271 (4)
C10—H100.9300N8—O61.214 (4)
C11—C121.380 (6)N8—O71.263 (5)
C11—H110.9300N8—O81.277 (5)
C12—N31.329 (4)N9—O91.220 (4)
C12—H120.9300N9—O111.272 (4)
C13—C151.514 (5)N9—O101.274 (4)
C13—H13A0.9600
O2—Tb1—O12155.19 (8)C10—C11—H11120.5
O2—Tb1—O774.92 (9)C12—C11—H11120.5
O12—Tb1—O7129.47 (9)N3—C12—C11123.7 (4)
O2—Tb1—O11116.88 (9)N3—C12—H12118.2
O12—Tb1—O1171.54 (9)C11—C12—H12118.2
O7—Tb1—O1176.45 (10)C15—C13—H13A109.5
O2—Tb1—O8122.52 (9)C15—C13—H13B109.5
O12—Tb1—O881.82 (9)H13A—C13—H13B109.5
O7—Tb1—O852.04 (10)C15—C13—H13C109.5
O11—Tb1—O874.29 (10)H13A—C13—H13C109.5
O2—Tb1—O5117.61 (8)H13B—C13—H13C109.5
O12—Tb1—O563.44 (8)C15—C14—H14A109.5
O7—Tb1—O5108.89 (9)C15—C14—H14B109.5
O11—Tb1—O5124.61 (9)H14A—C14—H14B109.5
O8—Tb1—O569.11 (10)C15—C14—H14C109.5
O2—Tb1—O474.03 (8)H14A—C14—H14C109.5
O12—Tb1—O4113.97 (8)H14B—C14—H14C109.5
O7—Tb1—O473.55 (10)N5—C15—C13108.4 (3)
O11—Tb1—O4143.77 (9)N5—C15—C14106.4 (3)
O8—Tb1—O471.39 (9)C13—C15—C14110.8 (3)
O5—Tb1—O450.79 (8)N5—C15—C16101.1 (3)
O2—Tb1—O1066.18 (9)C13—C15—C16115.4 (3)
O12—Tb1—O10114.46 (8)C14—C15—C16113.7 (3)
O7—Tb1—O1068.94 (10)N4—C16—C17109.6 (3)
O11—Tb1—O1051.20 (9)N4—C16—C18105.8 (3)
O8—Tb1—O10106.73 (10)C17—C16—C18110.0 (3)
O5—Tb1—O10175.35 (9)N4—C16—C15101.2 (3)
O4—Tb1—O10130.63 (8)C17—C16—C15115.9 (3)
O2—Tb1—N369.33 (8)C18—C16—C15113.5 (3)
O12—Tb1—N389.49 (8)C16—C17—H17A109.5
O7—Tb1—N3137.51 (9)C16—C17—H17B109.5
O11—Tb1—N3140.80 (9)H17A—C17—H17B109.5
O8—Tb1—N3138.05 (10)C16—C17—H17C109.5
O5—Tb1—N370.31 (9)H17A—C17—H17C109.5
O4—Tb1—N375.13 (9)H17B—C17—H17C109.5
O10—Tb1—N3114.14 (9)C16—C18—H18A109.5
O2—Tb1—N691.06 (8)C16—C18—H18B109.5
O12—Tb1—N668.48 (8)H18A—C18—H18B109.5
O7—Tb1—N6135.20 (10)C16—C18—H18C109.5
O11—Tb1—N672.62 (9)H18A—C18—H18C109.5
O8—Tb1—N6140.94 (10)H18B—C18—H18C109.5
O5—Tb1—N6115.22 (8)N5—C19—N4108.2 (3)
O4—Tb1—N6143.59 (9)N5—C19—C20126.7 (3)
O10—Tb1—N666.49 (9)N4—C19—C20125.1 (3)
N3—Tb1—N668.51 (9)N6—C20—C21122.7 (3)
C2—C1—H1A109.5N6—C20—C19116.8 (3)
C2—C1—H1B109.5C21—C20—C19120.5 (3)
H1A—C1—H1B109.5C20—C21—C22119.1 (4)
C2—C1—H1C109.5C20—C21—H21120.4
H1A—C1—H1C109.5C22—C21—H21120.4
H1B—C1—H1C109.5C23—C22—C21118.3 (4)
N2—C2—C3109.7 (3)C23—C22—H22120.8
N2—C2—C1105.9 (3)C21—C22—H22120.8
C3—C2—C1110.6 (3)C22—C23—C24118.6 (4)
N2—C2—C599.9 (3)C22—C23—H23120.7
C3—C2—C5115.4 (3)C24—C23—H23120.7
C1—C2—C5114.4 (3)N6—C24—C23124.6 (4)
C2—C3—H3A109.5N6—C24—H24117.7
C2—C3—H3B109.5C23—C24—H24117.7
H3A—C3—H3B109.5O1—N1—C7126.0 (3)
C2—C3—H3C109.5O1—N1—C5122.1 (3)
H3A—C3—H3C109.5C7—N1—C5110.4 (3)
H3B—C3—H3C109.5O2—N2—C7126.6 (3)
C5—C4—H4A109.5O2—N2—C2120.1 (3)
C5—C4—H4B109.5C7—N2—C2112.7 (3)
H4A—C4—H4B109.5C12—N3—C8117.2 (3)
C5—C4—H4C109.5C12—N3—Tb1112.1 (3)
H4A—C4—H4C109.5C8—N3—Tb1129.8 (2)
H4B—C4—H4C109.5O13—N4—C19125.1 (3)
N1—C5—C6105.6 (3)O13—N4—C16121.9 (3)
N1—C5—C4109.4 (3)C19—N4—C16112.3 (3)
C6—C5—C4110.2 (3)O12—N5—C19125.1 (3)
N1—C5—C2100.6 (3)O12—N5—C15120.2 (3)
C6—C5—C2114.6 (3)C19—N5—C15114.5 (3)
C4—C5—C2115.4 (4)C24—N6—C20116.4 (3)
C5—C6—H6A109.5C24—N6—Tb1112.0 (2)
C5—C6—H6B109.5C20—N6—Tb1129.2 (2)
H6A—C6—H6B109.5O3—N7—O5121.6 (3)
C5—C6—H6C109.5O3—N7—O4121.9 (3)
H6A—C6—H6C109.5O5—N7—O4116.5 (3)
H6B—C6—H6C109.5O6—N8—O7122.1 (4)
N2—C7—N1109.0 (3)O6—N8—O8121.6 (4)
N2—C7—C8125.4 (3)O7—N8—O8116.3 (3)
N1—C7—C8125.5 (3)O9—N9—O11121.0 (4)
N3—C8—C9123.0 (3)O9—N9—O10122.8 (4)
N3—C8—C7117.0 (3)O11—N9—O10116.2 (3)
C9—C8—C7119.9 (3)N2—O2—Tb1126.72 (19)
C8—C9—C10118.1 (4)N7—O4—Tb194.75 (18)
C8—C9—H9120.9N7—O5—Tb196.88 (19)
C10—C9—H9120.9N8—O7—Tb196.3 (2)
C11—C10—C9118.9 (4)N8—O8—Tb195.3 (2)
C11—C10—H10120.5N9—O10—Tb194.5 (2)
C9—C10—H10120.5N9—O11—Tb198.1 (2)
C10—C11—C12119.0 (4)N5—O12—Tb1129.14 (19)
N2—C2—C5—N124.8 (3)C19—C20—N6—Tb123.2 (5)
C3—C2—C5—N1142.3 (3)O2—Tb1—N6—C2411.2 (3)
C1—C2—C5—N187.8 (4)O12—Tb1—N6—C24154.4 (3)
N2—C2—C5—C687.9 (3)O7—Tb1—N6—C2480.7 (3)
C3—C2—C5—C629.6 (5)O11—Tb1—N6—C24129.1 (3)
C1—C2—C5—C6159.5 (3)O8—Tb1—N6—C24162.4 (2)
N2—C2—C5—C4142.4 (3)O5—Tb1—N6—C24110.2 (3)
C3—C2—C5—C4100.1 (4)O4—Tb1—N6—C2452.8 (3)
C1—C2—C5—C429.8 (5)O10—Tb1—N6—C2474.6 (3)
N2—C7—C8—N330.5 (5)N3—Tb1—N6—C2456.0 (3)
N1—C7—C8—N3144.5 (4)O2—Tb1—N6—C20172.7 (3)
N2—C7—C8—C9153.1 (4)O12—Tb1—N6—C207.1 (3)
N1—C7—C8—C931.9 (6)O7—Tb1—N6—C20117.8 (3)
N3—C8—C9—C103.3 (6)O11—Tb1—N6—C2069.4 (3)
C7—C8—C9—C10172.9 (4)O8—Tb1—N6—C2036.1 (4)
C8—C9—C10—C110.6 (7)O5—Tb1—N6—C2051.3 (3)
C9—C10—C11—C122.5 (7)O4—Tb1—N6—C20108.7 (3)
C10—C11—C12—N30.9 (7)O10—Tb1—N6—C20123.9 (3)
N5—C15—C16—N414.8 (3)N3—Tb1—N6—C20105.5 (3)
C13—C15—C16—N4131.5 (3)C7—N2—O2—Tb159.6 (4)
C14—C15—C16—N498.8 (3)C2—N2—O2—Tb1129.8 (3)
N5—C15—C16—C17133.3 (3)O12—Tb1—O2—N279.2 (3)
C13—C15—C16—C17110.0 (4)O7—Tb1—O2—N2110.4 (2)
C14—C15—C16—C1719.7 (5)O11—Tb1—O2—N2176.3 (2)
N5—C15—C16—C1898.0 (3)O8—Tb1—O2—N288.4 (3)
C13—C15—C16—C1818.7 (5)O5—Tb1—O2—N26.7 (3)
C14—C15—C16—C18148.3 (4)O4—Tb1—O2—N233.6 (2)
N5—C19—C20—N635.5 (6)O10—Tb1—O2—N2176.3 (3)
N4—C19—C20—N6144.9 (3)N3—Tb1—O2—N246.2 (2)
N5—C19—C20—C21144.4 (4)N6—Tb1—O2—N2112.7 (2)
N4—C19—C20—C2135.2 (6)O3—N7—O4—Tb1169.6 (3)
N6—C20—C21—C220.7 (6)O5—N7—O4—Tb110.4 (3)
C19—C20—C21—C22179.4 (4)O2—Tb1—O4—N7154.9 (2)
C20—C21—C22—C233.7 (7)O12—Tb1—O4—N70.1 (2)
C21—C22—C23—C244.4 (7)O7—Tb1—O4—N7126.5 (2)
C22—C23—C24—N60.9 (7)O11—Tb1—O4—N791.3 (2)
N2—C7—N1—O1179.9 (4)O8—Tb1—O4—N771.8 (2)
C8—C7—N1—O14.2 (6)O5—Tb1—O4—N76.03 (18)
N2—C7—N1—C513.8 (4)O10—Tb1—O4—N7168.19 (18)
C8—C7—N1—C5161.8 (3)N3—Tb1—O4—N782.5 (2)
C6—C5—N1—O172.5 (4)N6—Tb1—O4—N785.7 (2)
C4—C5—N1—O146.2 (5)O3—N7—O5—Tb1169.4 (3)
C2—C5—N1—O1168.1 (4)O4—N7—O5—Tb110.6 (3)
C6—C5—N1—C794.2 (4)O2—Tb1—O5—N740.3 (2)
C4—C5—N1—C7147.2 (4)O12—Tb1—O5—N7167.6 (2)
C2—C5—N1—C725.2 (4)O7—Tb1—O5—N742.2 (2)
N1—C7—N2—O2175.9 (3)O11—Tb1—O5—N7128.4 (2)
C8—C7—N2—O28.4 (6)O8—Tb1—O5—N776.4 (2)
N1—C7—N2—C24.7 (4)O4—Tb1—O5—N76.13 (19)
C8—C7—N2—C2179.6 (3)N3—Tb1—O5—N792.7 (2)
C3—C2—N2—O246.7 (4)N6—Tb1—O5—N7145.9 (2)
C1—C2—N2—O272.7 (4)O6—N8—O7—Tb1175.6 (4)
C5—C2—N2—O2168.3 (3)O8—N8—O7—Tb13.7 (4)
C3—C2—N2—C7141.5 (3)O2—Tb1—O7—N8154.2 (3)
C1—C2—N2—C799.2 (4)O12—Tb1—O7—N831.0 (3)
C5—C2—N2—C719.8 (4)O11—Tb1—O7—N882.7 (2)
C11—C12—N3—C82.8 (5)O8—Tb1—O7—N82.2 (2)
C11—C12—N3—Tb1167.1 (3)O5—Tb1—O7—N839.7 (3)
C9—C8—N3—C124.9 (5)O4—Tb1—O7—N876.8 (2)
C7—C8—N3—C12171.4 (3)O10—Tb1—O7—N8135.9 (3)
C9—C8—N3—Tb1162.9 (3)N3—Tb1—O7—N8120.9 (2)
C7—C8—N3—Tb120.9 (4)N6—Tb1—O7—N8129.9 (2)
O2—Tb1—N3—C12159.6 (3)O6—N8—O8—Tb1175.6 (4)
O12—Tb1—N3—C127.2 (2)O7—N8—O8—Tb13.7 (4)
O7—Tb1—N3—C12165.9 (2)O2—Tb1—O8—N825.2 (3)
O11—Tb1—N3—C1252.0 (3)O12—Tb1—O8—N8160.0 (3)
O8—Tb1—N3—C1284.3 (3)O7—Tb1—O8—N82.1 (2)
O5—Tb1—N3—C1269.1 (2)O11—Tb1—O8—N887.0 (2)
O4—Tb1—N3—C12122.2 (2)O5—Tb1—O8—N8135.3 (3)
O10—Tb1—N3—C12109.5 (2)O4—Tb1—O8—N881.2 (2)
N6—Tb1—N3—C1259.8 (2)O10—Tb1—O8—N846.9 (3)
O2—Tb1—N3—C88.7 (3)N3—Tb1—O8—N8119.9 (2)
O12—Tb1—N3—C8175.4 (3)N6—Tb1—O8—N8120.0 (2)
O7—Tb1—N3—C825.9 (3)O9—N9—O10—Tb1178.7 (3)
O11—Tb1—N3—C8116.2 (3)O11—N9—O10—Tb11.4 (3)
O8—Tb1—N3—C8107.4 (3)O2—Tb1—O10—N9172.4 (2)
O5—Tb1—N3—C8122.7 (3)O12—Tb1—O10—N934.8 (2)
O4—Tb1—N3—C869.5 (3)O7—Tb1—O10—N990.1 (2)
O10—Tb1—N3—C858.7 (3)O11—Tb1—O10—N90.85 (18)
N6—Tb1—N3—C8108.5 (3)O8—Tb1—O10—N953.7 (2)
N5—C19—N4—O13178.9 (3)N3—Tb1—O10—N9135.97 (19)
C20—C19—N4—O131.5 (6)N6—Tb1—O10—N985.2 (2)
N5—C19—N4—C167.9 (4)O9—N9—O11—Tb1178.6 (3)
C20—C19—N4—C16172.4 (3)O10—N9—O11—Tb11.5 (3)
C17—C16—N4—O1350.9 (5)O2—Tb1—O11—N99.5 (2)
C18—C16—N4—O1367.6 (4)O12—Tb1—O11—N9145.1 (2)
C15—C16—N4—O13173.8 (3)O7—Tb1—O11—N974.6 (2)
C17—C16—N4—C19137.8 (3)O8—Tb1—O11—N9128.4 (2)
C18—C16—N4—C19103.7 (3)O5—Tb1—O11—N9178.35 (18)
C15—C16—N4—C1914.9 (4)O4—Tb1—O11—N9109.3 (2)
N4—C19—N5—O12177.7 (3)O10—Tb1—O11—N90.86 (18)
C20—C19—N5—O121.9 (6)N3—Tb1—O11—N980.2 (2)
N4—C19—N5—C153.4 (4)N6—Tb1—O11—N972.6 (2)
C20—C19—N5—C15176.3 (3)C19—N5—O12—Tb155.5 (4)
C13—C15—N5—O1251.4 (4)C15—N5—O12—Tb1130.4 (3)
C14—C15—N5—O1267.9 (4)O2—Tb1—O12—N582.1 (3)
C16—C15—N5—O12173.1 (3)O7—Tb1—O12—N585.8 (3)
C13—C15—N5—C19134.0 (3)O11—Tb1—O12—N532.3 (2)
C14—C15—N5—C19106.7 (4)O8—Tb1—O12—N5108.4 (3)
C16—C15—N5—C1912.3 (4)O5—Tb1—O12—N5179.1 (3)
C23—C24—N6—C203.4 (6)O4—Tb1—O12—N5173.8 (2)
C23—C24—N6—Tb1160.7 (3)O10—Tb1—O12—N53.7 (3)
C21—C20—N6—C244.1 (5)N3—Tb1—O12—N5112.8 (3)
C19—C20—N6—C24176.0 (3)N6—Tb1—O12—N545.8 (2)
C21—C20—N6—Tb1156.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O13i0.932.553.440 (5)161
C17—H17B···O6ii0.962.403.327 (5)161
C6—H6B···O3iii0.962.553.473 (5)161
C24—H24···O9iv0.932.383.211 (5)148
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x+1, y+2, z; (iv) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Tb(NO3)3(C12H16N3O2)2]
Mr813.51
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)12.292 (3), 11.114 (2), 23.264 (5)
β (°) 98.37 (3)
V3)3144.6 (11)
Z4
Radiation typeMo Kα
µ (mm1)2.33
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.581, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
25443, 5554, 4726
Rint0.059
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.071, 1.01
No. of reflections5554
No. of parameters432
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.89, 0.95

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O13i0.932.553.440 (5)161
C17—H17B···O6ii0.962.403.327 (5)161
C6—H6B···O3iii0.962.553.473 (5)161
C24—H24···O9iv0.932.383.211 (5)148
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x+1, y+2, z; (iv) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

The author thanks the Chemical Institute of Linyi University for supporting this work.

References

First citationKahn, M. L., Sutter, J. P. & Golhen, S. (2000). J. Am. Chem. Soc. 122, 3413–3421.  Web of Science CSD CrossRef CAS
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First citationLi, D.-J. (2012). Acta Cryst. E68, m550.  CSD CrossRef IUCr Journals
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First citationLi, D.-J., Liao, D.-Z. & Li, L.-C. (2005). Chin. J. Struct. Chem. 24, 905–908.
First citationLi, D.-J., Yan, S.-P. & Liao, D.-Z. (2004b). J. Mol. Struct. 698, 103–107.  Web of Science CSD CrossRef CAS
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSutter, J. P., Kahn, M. L. & Golhen, S. (1998). Chem. Eur. J. 4, 571–576.  CrossRef CAS

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