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Acta Cryst. (2007). E63, m2625-m2626    [ doi:10.1107/S1600536807047101 ]

Hexakis([mu]-naphthalene-1-acetato)bis[(1,10-phenanthroline)gadolinium(III)] N,N-dimethylformamide disolvate

Y.-F. Liu, H.-T. Xia, D.-Q. Wang and S.-P. Yang

Abstract top

The title complex, [Gd2(C12H9O2)6(C12H8N2)2]·2C3H7NO, has a centrosymmetric structure. The Gd atom has a distorted monocapped square-antiprismatic coordination geometry. Molecules are linked into a chain by C-H...O hydrogen bonds parallel to a and into a sheet by C-H...[pi] hydrogen bonds parallel to the (100) plane; a combination of the a chains and (100) sheets generates a three-dimensional framework structure.

Comment top

As a part of our investigation of the rare earth complexes with 1-naphthylacetic acid (NAA) and 1,10-phenanthroline (phen), we have recently reported the crystal structures of two complexes [Eu(NAA)3(phen)]2.2DMF (II) (Liu et al., 2007) and [Pr(NAA)3(phen)]2 .DMF (Xia et al., 2007). We report here the crystal structure of gadolinium complexes with NAA and phen, (I).

In the title complex, the coordination environment of Gd atom and coordination modes of the NNA ligands coordinated to the GdIII ion are in agreement with the complex (II) (Fig.1). The average bond lengths of between the terbium center and carboxylic oxygen atoms are 2.450 (7) Å, shorter than that 2.4725 (5) Å) of complex (II). The dihedral angles of the least-square-plane Gd2O2 and naphthyl rings are 58.35 (20)° (C3—C12 ring), 43.84 (29)° (C15—C24 ring) and 71.45 (26)° (C27—C36 ring), and the dihedral angle between Gd2O2 plane and phen ring is 81.89 (20)°.

The molecules of (I) are linked into sheets by means of C—H···π hydrogen bond (Fig. 2 and Table 2) and chains parallel to the a axis direction with R44(30) rings (Bernstein et al., 1995) surrounds an R22(14) ring centred at (n, 1/2, 1) (n = zero or integer) (Fig. 3) by C—H···O hydrogen bonds (Fig. 3 and Table 2). The action of a chains are to link adjacent [100] sheet into the three-dimensional framework structure.

Related literature top

For related literature, see: Bernstein et al. (1995); Liu et al. (2007); Xia et al. (2007).

Experimental top

To a stirred solution of 1-naphthylacetic acid (0.5586 g, 3 mmol) and 1,10-phenanthroline monohydrate (0.198 g, 1 mmol) in 30 ml me thanol, and a solution of Gd(NO3)3·6H2O (0.451 g, 1 mmol) in water (10 ml) was added. The mixed solution was heated to 333k and stirred for 3 h, and then cooled to room temperature. The precipitate was washed with water and then dissolved in DMF. A colorless crystal suitable for X-ray diffraction was obtained by evaporation of DMF solution.

Refinement top

The space group was uniquely assigned from the systematic absences. 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 (aryl, formyl), 0.97Å (methylene) and 0.96 Å (methyl), and with Uiso(H) = 1.2Ueq(C) (aryl, 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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level. Unlabelled atoms in the molecular are related to labelled atoms by (1 − x, 1 − y, 2 − z).
[Figure 2] Fig. 2. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chain built from C—H···π. For clarty, H atomes not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [symmetry code: (A) 2 − x, 1 − y, 1 − z, (B) 2 − x, −1/2 + y, 1/2 − z, (C) x, 3/2 − y, 1/2 + z, (D) x, 1/2 − y, 1/2 + z, (E) 2 − x, 1/2 + y, 1/2 − z].
[Figure 3] Fig. 3. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chain built from C—H···O. For clarty, H atomes not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [symmetry code: (F) 1 − x, 1 − y, 1 + z,, (G) 1 − x, −1/2 + y, 3/2 − z].
Hexakis(µ-naphthalene-1-acetato)bis[(1,10-phenanthroline)gadolinium(III)] N,N-dimethylformamide disolvate top
Crystal data top
[Gd2(C12H9O2)6(C12H8N2)2]·2C3H7NOF000 = 1956
Mr = 1932.25Dx = 1.463 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4868 reflections
a = 13.4762 (19) Åθ = 2.4–25.3º
b = 15.103 (2) ŵ = 1.57 mm−1
c = 22.178 (2) ÅT = 298 (2) K
β = 103.698 (2)ºBlock, colourless
V = 4385.4 (10) Å30.43 × 0.16 × 0.15 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		7696 independent reflections
Radiation source: fine-focus sealed tube4921 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.055
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→15
Tmin = 0.552, Tmax = 0.799k = −17→12
20263 measured reflectionsl = −24→26
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.081  w = 1/[σ2(Fo2) + (0.0215P)2 + 3.2792P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
7696 reflectionsΔρmax = 1.01 e Å−3
561 parametersΔρmin = −0.80 e Å−3
36 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Gd2(C12H9O2)6(C12H8N2)2]·2C3H7NOV = 4385.4 (10) Å3
Mr = 1932.25Z = 2
Monoclinic, P21/cMo Kα
a = 13.4762 (19) ŵ = 1.57 mm−1
b = 15.103 (2) ÅT = 298 (2) K
c = 22.178 (2) Å0.43 × 0.16 × 0.15 mm
β = 103.698 (2)º
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		7696 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4921 reflections with I > 2σ(I)
Tmin = 0.552, Tmax = 0.799Rint = 0.055
20263 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04136 restraints
wR(F2) = 0.081H-atom parameters constrained
S = 1.03Δρmax = 1.01 e Å−3
7696 reflectionsΔρmin = −0.80 e Å−3
561 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
xyzUiso*/Ueq
Gd10.882546 (19)0.429745 (18)0.511490 (12)0.03439 (9)
N10.7300 (3)0.4440 (3)0.5645 (2)0.0422 (11)
N20.7124 (3)0.3633 (3)0.4537 (2)0.0505 (12)
N30.1327 (6)0.8355 (5)0.7469 (3)0.0839 (19)
O10.9404 (2)0.5795 (2)0.47896 (14)0.0378 (8)
O20.7765 (2)0.5557 (2)0.46141 (15)0.0457 (10)
O30.9045 (2)0.4248 (2)0.40872 (14)0.0407 (8)
O41.0488 (3)0.4869 (2)0.39721 (15)0.0432 (9)
O50.9128 (3)0.2727 (3)0.48857 (18)0.0554 (11)
O60.9031 (3)0.3045 (3)0.58324 (17)0.0555 (11)
O70.2671 (5)0.7448 (5)0.7639 (3)0.167 (3)
C10.8487 (4)0.5984 (3)0.4517 (2)0.0375 (13)
C20.8341 (4)0.6733 (4)0.4055 (3)0.0562 (17)
H2A0.85920.72730.42750.067*
H2B0.87600.66170.37630.067*
C30.7266 (4)0.6887 (4)0.3695 (3)0.0501 (16)
C40.6767 (5)0.7631 (5)0.3803 (3)0.070 (2)
H40.70990.80270.41060.084*
C50.5768 (6)0.7819 (5)0.3473 (4)0.086 (2)
H50.54480.83360.35550.103*
C60.5272 (5)0.7250 (6)0.3038 (4)0.082 (2)
H60.46030.73710.28270.099*
C70.5746 (5)0.6482 (5)0.2899 (3)0.0670 (19)
C80.6755 (5)0.6291 (5)0.3233 (3)0.0557 (17)
C90.7209 (6)0.5511 (5)0.3087 (3)0.081 (2)
H90.78740.53790.33000.097*
C100.6713 (8)0.4947 (6)0.2646 (4)0.121 (3)
H100.70310.44330.25580.145*
C110.5716 (9)0.5142 (7)0.2324 (4)0.126 (4)
H110.53690.47530.20210.151*
C120.5251 (6)0.5889 (6)0.2445 (4)0.101 (3)
H120.45880.60110.22230.121*
C130.9738 (4)0.4363 (4)0.3807 (2)0.0372 (12)
C140.9632 (4)0.3856 (4)0.3204 (2)0.0565 (17)
H14A0.91480.33790.31970.068*
H14B0.93400.42530.28640.068*
C151.0584 (5)0.3468 (4)0.3082 (3)0.0538 (16)
C161.0911 (6)0.3718 (5)0.2565 (3)0.076 (2)
H161.05430.41460.23040.092*
C171.1773 (7)0.3353 (6)0.2419 (4)0.097 (3)
H171.19810.35480.20710.116*
C181.2305 (6)0.2718 (6)0.2783 (4)0.093 (3)
H181.28830.24830.26830.112*
C191.2010 (5)0.2402 (5)0.3310 (4)0.074 (2)
C201.1143 (5)0.2798 (4)0.3467 (3)0.0571 (17)
C211.0848 (6)0.2471 (5)0.3991 (3)0.075 (2)
H211.02920.27210.41090.090*
C221.1363 (7)0.1797 (5)0.4324 (4)0.095 (3)
H221.11520.15910.46690.114*
C231.2197 (7)0.1402 (6)0.4169 (5)0.108 (3)
H231.25340.09350.44050.129*
C241.2515 (6)0.1704 (6)0.3673 (5)0.100 (3)
H241.30790.14430.35700.120*
C250.9101 (4)0.2498 (4)0.5422 (3)0.0506 (15)
C260.9136 (5)0.1503 (4)0.5563 (3)0.0678 (18)
H26A0.98080.12760.55600.081*
H26B0.90260.14120.59750.081*
C270.8354 (6)0.1001 (4)0.5107 (3)0.072 (2)
C280.8583 (8)0.0475 (5)0.4667 (4)0.098 (3)
H280.92640.03980.46580.117*
C290.7823 (10)0.0038 (7)0.4221 (5)0.133 (4)
H290.8010−0.03300.39300.160*
C300.6834 (10)0.0148 (8)0.4211 (5)0.134 (4)
H300.6338−0.01280.39060.161*
C310.6544 (8)0.0675 (6)0.4657 (5)0.105 (3)
C320.7308 (7)0.1103 (5)0.5116 (4)0.076 (2)
C330.6992 (6)0.1631 (5)0.5555 (4)0.095 (3)
H330.74790.19170.58610.114*
C340.5973 (8)0.1733 (6)0.5541 (5)0.126 (4)
H340.57670.20770.58360.151*
C350.5259 (10)0.1311 (8)0.5075 (7)0.161 (6)
H350.45710.13900.50650.194*
C360.5502 (11)0.0801 (8)0.4644 (6)0.151 (5)
H360.49960.05330.43400.182*
C370.7367 (5)0.4833 (4)0.6186 (3)0.0583 (17)
H370.79960.50590.63960.070*
C380.6537 (5)0.4923 (5)0.6458 (3)0.072 (2)
H380.66200.51950.68420.086*
C390.5613 (5)0.4611 (4)0.6156 (3)0.070 (2)
H390.50540.46780.63310.085*
C400.5494 (4)0.4195 (4)0.5590 (3)0.0590 (17)
C410.6369 (4)0.4123 (3)0.5345 (2)0.0414 (14)
C420.6274 (4)0.3709 (4)0.4755 (3)0.0451 (15)
C430.5323 (4)0.3381 (4)0.4424 (3)0.0611 (18)
C440.5275 (6)0.2987 (5)0.3857 (3)0.084 (2)
H440.46540.27720.36260.101*
C450.6120 (5)0.2912 (5)0.3634 (3)0.087 (2)
H450.60910.26460.32520.104*
C460.7043 (5)0.3246 (4)0.3993 (3)0.0676 (19)
H460.76270.31920.38410.081*
C470.4541 (5)0.3857 (5)0.5243 (4)0.073 (2)
H470.39670.39050.54050.088*
C480.4457 (5)0.3476 (5)0.4695 (4)0.079 (2)
H480.38240.32650.44800.094*
C490.1908 (8)0.7742 (7)0.7788 (4)0.111 (3)
H490.17400.75180.81420.134*
C500.0442 (6)0.8672 (5)0.7663 (3)0.103 (3)
H50A0.03520.83310.80110.154*
H50B−0.01510.86130.73260.154*
H50C0.05380.92840.77790.154*
C510.1579 (8)0.8747 (7)0.6936 (4)0.169 (5)
H51A0.17660.93560.70220.254*
H51B0.09980.87160.65890.254*
H51C0.21410.84340.68390.254*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Gd10.02397 (14)0.03787 (15)0.04183 (15)−0.00299 (15)0.00883 (10)−0.00279 (15)
N10.030 (3)0.048 (3)0.051 (3)0.004 (2)0.013 (2)0.006 (2)
N20.035 (3)0.057 (3)0.058 (3)−0.008 (3)0.007 (2)−0.009 (3)
N30.093 (5)0.084 (5)0.071 (5)−0.008 (4)0.014 (4)−0.018 (4)
O10.0227 (19)0.043 (2)0.046 (2)0.0017 (18)0.0056 (16)−0.0015 (18)
O20.0218 (19)0.055 (3)0.062 (2)−0.0001 (19)0.0138 (17)0.011 (2)
O30.035 (2)0.050 (2)0.0388 (19)−0.007 (2)0.0123 (16)−0.0084 (19)
O40.036 (2)0.049 (2)0.046 (2)−0.011 (2)0.0124 (18)−0.0159 (18)
O50.058 (3)0.046 (3)0.065 (3)−0.004 (2)0.019 (2)−0.003 (2)
O60.059 (3)0.050 (3)0.060 (3)−0.004 (2)0.019 (2)0.000 (2)
O70.091 (5)0.200 (8)0.195 (7)0.008 (5)0.008 (5)−0.062 (6)
C10.026 (3)0.041 (4)0.045 (3)0.005 (3)0.006 (3)−0.004 (3)
C20.034 (4)0.065 (4)0.066 (4)−0.003 (3)0.005 (3)0.020 (3)
C30.038 (4)0.053 (4)0.060 (4)0.001 (3)0.012 (3)0.025 (3)
C40.057 (5)0.072 (5)0.075 (5)0.008 (4)0.002 (4)0.025 (4)
C50.073 (6)0.084 (6)0.101 (6)0.034 (5)0.023 (5)0.033 (5)
C60.045 (5)0.106 (7)0.091 (6)0.016 (5)0.007 (4)0.046 (5)
C70.047 (4)0.084 (6)0.061 (5)−0.005 (4)−0.005 (4)0.026 (4)
C80.050 (4)0.061 (5)0.055 (4)−0.003 (4)0.010 (3)0.022 (4)
C90.084 (5)0.085 (6)0.062 (5)0.013 (5)−0.008 (4)0.003 (4)
C100.157 (9)0.107 (7)0.076 (6)0.014 (7)−0.016 (6)−0.011 (5)
C110.162 (10)0.100 (7)0.081 (6)−0.023 (7)−0.040 (6)−0.005 (6)
C120.090 (6)0.113 (8)0.078 (6)−0.023 (6)−0.024 (5)0.028 (5)
C130.042 (3)0.039 (3)0.030 (3)0.007 (3)0.007 (3)−0.001 (3)
C140.053 (4)0.069 (4)0.045 (4)−0.004 (3)0.008 (3)−0.018 (3)
C150.054 (4)0.061 (4)0.049 (4)−0.006 (4)0.018 (3)−0.027 (3)
C160.096 (6)0.080 (5)0.062 (4)−0.006 (4)0.038 (4)−0.016 (4)
C170.115 (8)0.107 (8)0.089 (6)−0.005 (6)0.068 (6)−0.025 (5)
C180.065 (6)0.111 (8)0.117 (7)−0.014 (5)0.049 (5)−0.057 (6)
C190.060 (5)0.071 (6)0.097 (6)−0.005 (4)0.030 (5)−0.039 (5)
C200.049 (4)0.059 (4)0.063 (4)−0.009 (4)0.012 (3)−0.022 (4)
C210.081 (5)0.064 (5)0.081 (5)0.000 (4)0.024 (4)−0.012 (4)
C220.100 (7)0.076 (6)0.109 (7)0.007 (5)0.026 (6)0.000 (5)
C230.097 (8)0.081 (7)0.134 (8)0.013 (6)0.006 (6)0.001 (6)
C240.074 (6)0.083 (7)0.143 (9)0.001 (5)0.025 (6)−0.033 (6)
C250.031 (3)0.038 (4)0.079 (5)−0.007 (3)0.005 (3)0.005 (4)
C260.062 (5)0.047 (4)0.093 (5)0.002 (4)0.015 (4)0.010 (4)
C270.093 (6)0.041 (4)0.083 (5)−0.009 (4)0.021 (5)0.021 (4)
C280.156 (8)0.057 (5)0.086 (6)−0.010 (5)0.041 (6)−0.009 (4)
C290.233 (12)0.074 (6)0.100 (7)−0.041 (9)0.054 (9)−0.011 (5)
C300.188 (10)0.093 (7)0.103 (7)−0.056 (9)−0.002 (8)0.013 (6)
C310.107 (6)0.063 (5)0.127 (7)−0.032 (6)−0.004 (6)0.033 (5)
C320.091 (6)0.041 (4)0.086 (5)−0.019 (4)0.000 (5)0.012 (4)
C330.078 (6)0.060 (5)0.153 (8)−0.015 (5)0.038 (6)0.005 (5)
C340.102 (8)0.076 (7)0.216 (11)−0.018 (6)0.069 (8)0.027 (7)
C350.099 (8)0.096 (10)0.266 (16)−0.039 (8)0.000 (10)0.067 (9)
C360.124 (9)0.098 (8)0.200 (11)−0.047 (9)−0.028 (9)0.051 (7)
C370.044 (4)0.076 (5)0.061 (4)0.002 (3)0.023 (3)0.006 (4)
C380.068 (5)0.085 (6)0.074 (5)0.002 (4)0.038 (4)0.004 (4)
C390.059 (5)0.071 (5)0.097 (6)0.014 (4)0.051 (4)0.026 (4)
C400.041 (4)0.064 (5)0.081 (5)0.011 (4)0.032 (3)0.028 (4)
C410.030 (3)0.040 (4)0.056 (4)0.007 (3)0.014 (3)0.019 (3)
C420.024 (3)0.043 (4)0.067 (4)−0.005 (3)0.008 (3)0.011 (3)
C430.033 (4)0.057 (4)0.091 (5)−0.014 (3)0.011 (4)0.010 (4)
C440.058 (5)0.088 (6)0.091 (6)−0.032 (5)−0.010 (4)−0.014 (5)
C450.063 (5)0.116 (7)0.076 (5)−0.038 (5)0.004 (4)−0.030 (5)
C460.049 (4)0.088 (5)0.065 (4)−0.024 (4)0.012 (4)−0.025 (4)
C470.021 (4)0.082 (6)0.119 (6)−0.003 (3)0.021 (4)0.042 (5)
C480.034 (4)0.079 (6)0.116 (6)−0.015 (4)0.006 (4)0.029 (5)
C490.090 (8)0.133 (10)0.102 (7)0.001 (7)0.003 (6)−0.018 (6)
C500.105 (7)0.096 (7)0.099 (6)0.009 (5)0.008 (5)−0.035 (5)
C510.241 (13)0.173 (11)0.114 (8)−0.071 (10)0.083 (8)0.013 (7)
Geometric parameters (Å, °) top
Gd1—O1i2.349 (3)C19—C241.402 (10)
Gd1—O32.368 (3)C19—C201.427 (8)
Gd1—O4i2.378 (3)C20—C211.403 (8)
Gd1—O62.445 (4)C21—C221.350 (9)
Gd1—O22.478 (3)C21—H210.9300
Gd1—O52.480 (4)C22—C231.385 (10)
Gd1—O12.551 (3)C22—H220.9300
Gd1—N22.552 (4)C23—C241.352 (10)
Gd1—N12.608 (4)C23—H230.9300
Gd1—Gd1i3.9431 (7)C24—H240.9300
N1—C371.322 (6)C25—C261.533 (7)
N1—C411.360 (6)C26—C271.484 (9)
N2—C461.323 (6)C26—H26A0.9700
N2—C421.349 (6)C26—H26B0.9700
N3—C491.308 (10)C27—C281.349 (9)
N3—C511.433 (9)C27—C321.424 (10)
N3—C501.442 (9)C28—C291.408 (12)
O1—C11.273 (5)C28—H280.9300
O1—Gd1i2.349 (3)C29—C301.338 (13)
O2—C11.228 (6)C29—H290.9300
O3—C131.250 (5)C30—C311.395 (13)
O4—C131.252 (6)C30—H300.9300
O4—Gd1i2.378 (3)C31—C361.411 (15)
O5—C251.246 (7)C31—C321.421 (10)
O6—C251.250 (7)C32—C331.400 (10)
O7—C491.235 (10)C33—C341.375 (10)
C1—C21.508 (7)C33—H330.9300
C2—C31.498 (7)C34—C351.388 (14)
C2—H2A0.9700C34—H340.9300
C2—H2B0.9700C35—C361.327 (15)
C3—C41.360 (8)C35—H350.9300
C3—C81.414 (8)C36—H360.9300
C4—C51.400 (8)C37—C381.397 (8)
C4—H40.9300C37—H370.9300
C5—C61.346 (9)C38—C391.351 (8)
C5—H50.9300C38—H380.9300
C6—C71.394 (9)C39—C401.378 (8)
C6—H60.9300C39—H390.9300
C7—C121.393 (9)C40—C411.414 (7)
C7—C81.416 (8)C40—C471.426 (8)
C8—C91.400 (8)C41—C421.430 (7)
C9—C101.349 (9)C42—C431.408 (7)
C9—H90.9300C43—C441.379 (8)
C10—C111.395 (11)C43—C481.440 (9)
C10—H100.9300C44—C451.350 (9)
C11—C121.349 (11)C44—H440.9300
C11—H110.9300C45—C461.402 (8)
C12—H120.9300C45—H450.9300
C13—C141.519 (7)C46—H460.9300
C14—C151.492 (7)C47—C481.325 (9)
C14—H14A0.9700C47—H470.9300
C14—H14B0.9700C48—H480.9300
C15—C161.373 (8)C49—H490.9300
C15—C201.420 (8)C50—H50A0.9600
C16—C171.391 (9)C50—H50B0.9600
C16—H160.9300C50—H50C0.9600
C17—C181.345 (10)C51—H51A0.9600
C17—H170.9300C51—H51B0.9600
C18—C191.404 (10)C51—H51C0.9600
C18—H180.9300
O1i—Gd1—O374.30 (10)C17—C16—H16118.8
O1i—Gd1—O4i76.87 (11)C18—C17—C16119.9 (8)
O3—Gd1—O4i136.41 (12)C18—C17—H17120.1
O1i—Gd1—O686.51 (12)C16—C17—H17120.1
O3—Gd1—O6125.56 (13)C17—C18—C19121.7 (8)
O4i—Gd1—O683.91 (13)C17—C18—H18119.2
O1i—Gd1—O2123.47 (12)C19—C18—H18119.2
O3—Gd1—O277.45 (11)C24—C19—C18122.6 (8)
O4i—Gd1—O292.41 (12)C24—C19—C20119.3 (8)
O6—Gd1—O2148.21 (12)C18—C19—C20118.1 (8)
O1i—Gd1—O575.45 (12)C21—C20—C15122.4 (6)
O3—Gd1—O573.07 (13)C21—C20—C19117.6 (7)
O4i—Gd1—O5129.15 (13)C15—C20—C19120.0 (7)
O6—Gd1—O552.75 (12)C22—C21—C20120.6 (7)
O2—Gd1—O5138.38 (12)C22—C21—H21119.7
O1i—Gd1—O172.92 (13)C20—C21—H21119.7
O3—Gd1—O168.86 (11)C21—C22—C23122.0 (8)
O4i—Gd1—O171.83 (11)C21—C22—H22119.0
O6—Gd1—O1150.99 (11)C23—C22—H22119.0
O2—Gd1—O151.34 (10)C24—C23—C22119.3 (9)
O5—Gd1—O1135.55 (12)C24—C23—H23120.3
O1i—Gd1—N2142.61 (13)C22—C23—H23120.3
O3—Gd1—N278.84 (13)C23—C24—C19121.1 (9)
O4i—Gd1—N2139.25 (13)C23—C24—H24119.5
O6—Gd1—N288.45 (14)C19—C24—H24119.5
O2—Gd1—N273.88 (13)O5—C25—O6122.4 (6)
O5—Gd1—N272.12 (14)O5—C25—C26117.4 (6)
O1—Gd1—N2120.31 (13)O6—C25—C26120.2 (6)
O1i—Gd1—N1148.94 (12)C27—C26—C25112.3 (5)
O3—Gd1—N1136.73 (12)C27—C26—H26A109.1
O4i—Gd1—N176.19 (13)C25—C26—H26A109.1
O6—Gd1—N175.55 (13)C27—C26—H26B109.1
O2—Gd1—N172.92 (12)C25—C26—H26B109.1
O5—Gd1—N1110.92 (13)H26A—C26—H26B107.9
O1—Gd1—N1112.36 (12)C28—C27—C32118.1 (8)
N2—Gd1—N163.16 (14)C28—C27—C26123.2 (8)
O1i—Gd1—Gd1i38.20 (8)C32—C27—C26118.7 (7)
O3—Gd1—Gd1i66.76 (8)C27—C28—C29122.1 (10)
O4i—Gd1—Gd1i70.30 (8)C27—C28—H28119.0
O6—Gd1—Gd1i121.98 (9)C29—C28—H28119.0
O2—Gd1—Gd1i85.67 (8)C30—C29—C28120.6 (12)
O5—Gd1—Gd1i108.19 (9)C30—C29—H29119.7
O1—Gd1—Gd1i34.72 (7)C28—C29—H29119.7
N2—Gd1—Gd1i143.12 (10)C29—C30—C31120.3 (12)
N1—Gd1—Gd1i139.16 (10)C29—C30—H30119.8
C37—N1—C41117.3 (5)C31—C30—H30119.8
C37—N1—Gd1123.7 (4)C30—C31—C36120.5 (12)
C41—N1—Gd1119.0 (3)C30—C31—C32119.4 (10)
C46—N2—C42118.1 (5)C36—C31—C32120.1 (11)
C46—N2—Gd1120.2 (4)C33—C32—C31118.1 (9)
C42—N2—Gd1121.7 (4)C33—C32—C27122.4 (7)
C49—N3—C51120.8 (9)C31—C32—C27119.5 (9)
C49—N3—C50120.4 (8)C34—C33—C32120.9 (9)
C51—N3—C50118.8 (8)C34—C33—H33119.6
C1—O1—Gd1i155.1 (3)C32—C33—H33119.6
C1—O1—Gd190.3 (3)C33—C34—C35118.6 (11)
Gd1i—O1—Gd1107.08 (13)C33—C34—H34120.7
C1—O2—Gd194.9 (3)C35—C34—H34120.7
C13—O3—Gd1138.8 (3)C36—C35—C34123.8 (15)
C13—O4—Gd1i134.1 (3)C36—C35—H35118.1
C25—O5—Gd191.5 (4)C34—C35—H35118.1
C25—O6—Gd193.1 (4)C35—C36—C31118.6 (14)
O2—C1—O1121.3 (5)C35—C36—H36120.7
O2—C1—C2122.2 (5)C31—C36—H36120.7
O1—C1—C2116.5 (5)N1—C37—C38123.0 (6)
C3—C2—C1115.7 (5)N1—C37—H37118.5
C3—C2—H2A108.4C38—C37—H37118.5
C1—C2—H2A108.4C39—C38—C37119.4 (6)
C3—C2—H2B108.4C39—C38—H38120.3
C1—C2—H2B108.4C37—C38—H38120.3
H2A—C2—H2B107.4C38—C39—C40120.3 (6)
C4—C3—C8118.6 (6)C38—C39—H39119.9
C4—C3—C2119.4 (6)C40—C39—H39119.9
C8—C3—C2122.0 (6)C39—C40—C41117.2 (6)
C3—C4—C5121.9 (7)C39—C40—C47123.4 (6)
C3—C4—H4119.0C41—C40—C47119.4 (6)
C5—C4—H4119.0N1—C41—C40122.8 (5)
C6—C5—C4119.9 (7)N1—C41—C42118.3 (5)
C6—C5—H5120.1C40—C41—C42118.9 (5)
C4—C5—H5120.1N2—C42—C43122.0 (6)
C5—C6—C7120.9 (7)N2—C42—C41117.8 (5)
C5—C6—H6119.5C43—C42—C41120.3 (5)
C7—C6—H6119.5C44—C43—C42117.9 (6)
C6—C7—C12121.9 (7)C44—C43—C48123.7 (7)
C6—C7—C8119.2 (7)C42—C43—C48118.4 (6)
C12—C7—C8118.9 (8)C45—C44—C43120.6 (6)
C9—C8—C3122.6 (6)C45—C44—H44119.7
C9—C8—C7118.0 (7)C43—C44—H44119.7
C3—C8—C7119.4 (7)C44—C45—C46118.3 (7)
C10—C9—C8122.0 (7)C44—C45—H45120.8
C10—C9—H9119.0C46—C45—H45120.8
C8—C9—H9119.0N2—C46—C45123.2 (6)
C9—C10—C11119.3 (9)N2—C46—H46118.4
C9—C10—H10120.3C45—C46—H46118.4
C11—C10—H10120.3C48—C47—C40121.4 (6)
C12—C11—C10120.7 (9)C48—C47—H47119.3
C12—C11—H11119.6C40—C47—H47119.3
C10—C11—H11119.6C47—C48—C43121.6 (7)
C11—C12—C7121.0 (8)C47—C48—H48119.2
C11—C12—H12119.5C43—C48—H48119.2
C7—C12—H12119.5O7—C49—N3122.6 (11)
O3—C13—O4125.9 (5)O7—C49—H49118.7
O3—C13—C14116.3 (5)N3—C49—H49118.7
O4—C13—C14117.7 (5)N3—C50—H50A109.5
C15—C14—C13116.9 (5)N3—C50—H50B109.5
C15—C14—H14A108.1H50A—C50—H50B109.5
C13—C14—H14A108.1N3—C50—H50C109.5
C15—C14—H14B108.1H50A—C50—H50C109.5
C13—C14—H14B108.1H50B—C50—H50C109.5
H14A—C14—H14B107.3N3—C51—H51A109.5
C16—C15—C20117.9 (6)N3—C51—H51B109.5
C16—C15—C14120.2 (6)H51A—C51—H51B109.5
C20—C15—C14121.8 (5)N3—C51—H51C109.5
C15—C16—C17122.4 (7)H51A—C51—H51C109.5
C15—C16—H16118.8H51B—C51—H51C109.5
O1i—Gd1—N1—C3727.8 (6)C6—C7—C8—C9179.5 (6)
O3—Gd1—N1—C37−148.5 (4)C12—C7—C8—C90.5 (9)
O4i—Gd1—N1—C37−2.8 (4)C6—C7—C8—C3−0.9 (9)
O6—Gd1—N1—C3784.4 (4)C12—C7—C8—C3−180.0 (6)
O2—Gd1—N1—C37−99.7 (4)C3—C8—C9—C10179.9 (7)
O5—Gd1—N1—C37124.3 (4)C7—C8—C9—C10−0.6 (10)
O1—Gd1—N1—C37−66.1 (4)C8—C9—C10—C110.1 (13)
N2—Gd1—N1—C37−179.9 (5)C9—C10—C11—C120.4 (15)
Gd1i—Gd1—N1—C37−38.1 (5)C10—C11—C12—C7−0.5 (15)
O1i—Gd1—N1—C41−154.6 (3)C6—C7—C12—C11−178.9 (8)
O3—Gd1—N1—C4129.1 (5)C8—C7—C12—C110.1 (12)
O4i—Gd1—N1—C41174.9 (4)Gd1—O3—C13—O4−29.4 (9)
O6—Gd1—N1—C41−97.9 (4)Gd1—O3—C13—C14152.4 (4)
O2—Gd1—N1—C4178.0 (4)Gd1i—O4—C13—O39.6 (8)
O5—Gd1—N1—C41−58.1 (4)Gd1i—O4—C13—C14−172.3 (3)
O1—Gd1—N1—C41111.6 (4)O3—C13—C14—C15−139.9 (5)
N2—Gd1—N1—C41−2.2 (3)O4—C13—C14—C1541.9 (8)
Gd1i—Gd1—N1—C41139.5 (3)C13—C14—C15—C16−120.2 (6)
O1i—Gd1—N2—C46−23.8 (6)C13—C14—C15—C2063.7 (8)
O3—Gd1—N2—C4620.8 (5)C20—C15—C16—C17−1.4 (10)
O4i—Gd1—N2—C46175.2 (4)C14—C15—C16—C17−177.7 (6)
O6—Gd1—N2—C46−105.9 (5)C15—C16—C17—C181.5 (12)
O2—Gd1—N2—C46100.8 (5)C16—C17—C18—C190.6 (13)
O5—Gd1—N2—C46−54.8 (5)C17—C18—C19—C24175.9 (8)
O1—Gd1—N2—C4678.1 (5)C17—C18—C19—C20−2.4 (11)
N1—Gd1—N2—C46179.5 (5)C16—C15—C20—C21−177.3 (6)
Gd1i—Gd1—N2—C4641.9 (6)C14—C15—C20—C21−1.1 (9)
O1i—Gd1—N2—C42160.1 (4)C16—C15—C20—C19−0.5 (9)
O3—Gd1—N2—C42−155.3 (4)C14—C15—C20—C19175.7 (5)
O4i—Gd1—N2—C42−0.9 (5)C24—C19—C20—C211.0 (9)
O6—Gd1—N2—C4277.9 (4)C18—C19—C20—C21179.3 (6)
O2—Gd1—N2—C42−75.3 (4)C24—C19—C20—C15−176.0 (6)
O5—Gd1—N2—C42129.1 (4)C18—C19—C20—C152.4 (9)
O1—Gd1—N2—C42−98.1 (4)C15—C20—C21—C22176.0 (6)
N1—Gd1—N2—C423.4 (4)C19—C20—C21—C22−0.9 (10)
Gd1i—Gd1—N2—C42−134.2 (4)C20—C21—C22—C230.1 (12)
O1i—Gd1—O1—C1162.0 (3)C21—C22—C23—C240.7 (13)
O3—Gd1—O1—C182.6 (3)C22—C23—C24—C19−0.6 (14)
O4i—Gd1—O1—C1−116.6 (3)C18—C19—C24—C23−178.5 (8)
O6—Gd1—O1—C1−151.3 (3)C20—C19—C24—C23−0.2 (12)
O2—Gd1—O1—C1−8.0 (3)Gd1—O5—C25—O6−5.3 (6)
O5—Gd1—O1—C1115.5 (3)Gd1—O5—C25—C26173.5 (5)
N2—Gd1—O1—C120.4 (3)Gd1—O6—C25—O55.4 (6)
N1—Gd1—O1—C1−50.6 (3)Gd1—O6—C25—C26−173.4 (5)
Gd1i—Gd1—O1—C1162.0 (3)O5—C25—C26—C27−51.9 (8)
O1i—Gd1—O1—Gd1i0.0O6—C25—C26—C27126.9 (7)
O3—Gd1—O1—Gd1i−79.35 (13)C25—C26—C27—C28106.7 (7)
O4i—Gd1—O1—Gd1i81.41 (13)C25—C26—C27—C32−70.7 (8)
O6—Gd1—O1—Gd1i46.7 (3)C32—C27—C28—C290.6 (11)
O2—Gd1—O1—Gd1i−169.97 (18)C26—C27—C28—C29−176.9 (7)
O5—Gd1—O1—Gd1i−46.5 (2)C27—C28—C29—C301.4 (15)
N2—Gd1—O1—Gd1i−141.55 (14)C28—C29—C30—C31−2.1 (17)
N1—Gd1—O1—Gd1i147.41 (13)C29—C30—C31—C36179.3 (10)
O1i—Gd1—O2—C1−3.2 (3)C29—C30—C31—C320.8 (15)
O3—Gd1—O2—C1−64.5 (3)C30—C31—C32—C33179.7 (8)
O4i—Gd1—O2—C172.7 (3)C36—C31—C32—C331.3 (12)
O6—Gd1—O2—C1155.0 (3)C30—C31—C32—C271.1 (11)
O5—Gd1—O2—C1−110.1 (3)C36—C31—C32—C27−177.3 (8)
O1—Gd1—O2—C18.3 (3)C28—C27—C32—C33179.7 (7)
N2—Gd1—O2—C1−146.3 (3)C26—C27—C32—C33−2.7 (10)
N1—Gd1—O2—C1147.4 (3)C28—C27—C32—C31−1.8 (10)
Gd1i—Gd1—O2—C12.6 (3)C26—C27—C32—C31175.8 (6)
O1i—Gd1—O3—C13−17.2 (5)C31—C32—C33—C34−0.2 (11)
O4i—Gd1—O3—C1333.2 (6)C27—C32—C33—C34178.4 (7)
O6—Gd1—O3—C13−91.0 (6)C32—C33—C34—C35−0.9 (13)
O2—Gd1—O3—C13113.3 (6)C33—C34—C35—C360.9 (18)
O5—Gd1—O3—C13−96.4 (6)C34—C35—C36—C310(2)
O1—Gd1—O3—C1360.2 (5)C30—C31—C36—C35−179.7 (11)
N2—Gd1—O3—C13−170.9 (6)C32—C31—C36—C35−1.3 (17)
N1—Gd1—O3—C13160.8 (5)C41—N1—C37—C380.7 (9)
Gd1i—Gd1—O3—C1322.6 (5)Gd1—N1—C37—C38178.4 (5)
O1i—Gd1—O5—C2599.7 (3)N1—C37—C38—C39−1.0 (10)
O3—Gd1—O5—C25177.3 (4)C37—C38—C39—C401.1 (10)
O4i—Gd1—O5—C2540.6 (4)C38—C39—C40—C41−0.8 (9)
O6—Gd1—O5—C252.9 (3)C38—C39—C40—C47−179.4 (6)
O2—Gd1—O5—C25−135.9 (3)C37—N1—C41—C40−0.4 (8)
O1—Gd1—O5—C25145.4 (3)Gd1—N1—C41—C40−178.2 (4)
N2—Gd1—O5—C25−99.2 (4)C37—N1—C41—C42179.0 (5)
N1—Gd1—O5—C25−48.4 (4)Gd1—N1—C41—C421.2 (6)
Gd1i—Gd1—O5—C25119.6 (3)C39—C40—C41—N10.4 (9)
O1i—Gd1—O6—C25−77.2 (3)C47—C40—C41—N1179.1 (5)
O3—Gd1—O6—C25−9.4 (4)C39—C40—C41—C42−179.0 (5)
O4i—Gd1—O6—C25−154.4 (3)C47—C40—C41—C42−0.3 (8)
O2—Gd1—O6—C25120.9 (4)C46—N2—C42—C430.7 (9)
O5—Gd1—O6—C25−2.9 (3)Gd1—N2—C42—C43176.9 (4)
O1—Gd1—O6—C25−121.4 (4)C46—N2—C42—C41179.6 (5)
N2—Gd1—O6—C2565.7 (3)Gd1—N2—C42—C41−4.2 (7)
N1—Gd1—O6—C25128.4 (3)N1—C41—C42—N21.9 (7)
Gd1i—Gd1—O6—C25−92.2 (3)C40—C41—C42—N2−178.7 (5)
Gd1—O2—C1—O1−15.4 (5)N1—C41—C42—C43−179.2 (5)
Gd1—O2—C1—C2162.3 (5)C40—C41—C42—C430.2 (8)
Gd1i—O1—C1—O2150.2 (6)N2—C42—C43—C44−1.1 (9)
Gd1—O1—C1—O214.9 (5)C41—C42—C43—C44−180.0 (6)
Gd1i—O1—C1—C2−27.7 (11)N2—C42—C43—C48178.9 (6)
Gd1—O1—C1—C2−163.0 (4)C41—C42—C43—C480.1 (9)
O2—C1—C2—C3−3.5 (8)C42—C43—C44—C450.8 (11)
O1—C1—C2—C3174.3 (5)C48—C43—C44—C45−179.2 (7)
C1—C2—C3—C4110.7 (6)C43—C44—C45—C46−0.1 (12)
C1—C2—C3—C8−70.7 (7)C42—N2—C46—C450.0 (10)
C8—C3—C4—C50.1 (9)Gd1—N2—C46—C45−176.3 (5)
C2—C3—C4—C5178.8 (6)C44—C45—C46—N2−0.3 (12)
C3—C4—C5—C60.6 (11)C39—C40—C47—C48178.7 (7)
C4—C5—C6—C7−1.5 (11)C41—C40—C47—C480.1 (10)
C5—C6—C7—C12−179.3 (7)C40—C47—C48—C430.2 (11)
C5—C6—C7—C81.7 (11)C44—C43—C48—C47179.7 (7)
C4—C3—C8—C9179.6 (6)C42—C43—C48—C47−0.3 (10)
C2—C3—C8—C90.9 (9)C51—N3—C49—O7−2.7 (14)
C4—C3—C8—C70.1 (8)C50—N3—C49—O7179.8 (8)
C2—C3—C8—C7−178.6 (5)
Symmetry codes: (i) −x+2, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C50—H50A···O6ii0.962.543.379 (9)146
C47—H47···O2iii0.932.463.319 (7)153
C6—H6···O7iv0.932.553.436 (10)159
C51—H51C···O70.962.302.713 (13)105
C46—H46···O30.932.453.057 (7)123
C37—H37···O4i0.932.373.027 (7)127
C21—H21···O50.932.593.412 (8)148
C18—H18···Cg1v0.932.883.66 (2)142
C39—H39···Cg2iii0.932.993.858 (18)156
Symmetry codes: (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) x, −y+3/2, z−1/2; (i) −x+2, −y+1, −z+1; (v) −x+2, y−1/2, −z+1/2.
Table 1
Selected geometric parameters (Å) top
Gd1—O1i2.349 (3)Gd1—O52.480 (4)
Gd1—O32.368 (3)Gd1—O12.551 (3)
Gd1—O4i2.378 (3)Gd1—N22.552 (4)
Gd1—O62.445 (4)Gd1—N12.608 (4)
Gd1—O22.478 (3)
Symmetry codes: (i) −x+2, −y+1, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C50—H50A···O6ii0.962.543.379 (9)146
C47—H47···O2iii0.932.463.319 (7)153
C6—H6···O7iv0.932.553.436 (10)159
C51—H51C···O70.962.302.713 (13)105
C46—H46···O30.932.453.057 (7)123
C37—H37···O4i0.932.373.027 (7)127
C21—H21···O50.932.593.412 (8)148
C18—H18···Cg1v0.932.883.66 (2)142
C39—H39···Cg2iii0.932.993.858 (18)156
Symmetry codes: (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) x, −y+3/2, z−1/2; (i) −x+2, −y+1, −z+1; (v) −x+2, y−1/2, −z+1/2.
Acknowledgements top

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

references
References top

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Liu, Y.-F., Xia, H.-T., Wang, D.-Q. & Yang, S.-P. (2007). Acta Cryst. E63, m0000–m0000 [AT2403].

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

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

Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.

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

Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Cheng, L. (2007). Acta Cryst. E63, m0000–m0000 [AT2404].