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Acta Cryst. (2009). E65, m614    [ doi:10.1107/S1600536809013440 ]

[13,27-Dichloro-3,6,9,17,20,23-hexaazatetracyclo[23.3.1.111,15.02,6]triaconta-1(29),9,11,13,15(30),16,23,25,27-nonaene-29,30-diol-[kappa]5N17,N20,N23,O29,O30]bis(nitrato-[kappa]2O,O')europium(III) nitrate methanol hemisolvate

X.-L. Yue

Abstract top

The title compound, [EuIII(NO3)2(C24H28Cl2N6O2)]NO3·0.5CH3OH, is isostructural with the GdIII and HoIII complexes of the analogous macrocyclic ligand, with both Cl atoms replaced by methyl groups. The Eu atom exhibits a nine-coordinate distorted tricapped trigonal-prismatic coordination geometry. The methanol solvent molecule is disordered about a twofold rotation axis with occupancies of 0.543 (12):0.457 (12).

Comment top

Lanthanide macrocyclic complexes have received attention on account of their many valuable applications, for example as fluorescent probes in biological systems and as new luminescent materials (Bunzli & Piguet, 2002; Alexander, 1995). Generally, the synthesis of lanthanide macrocyclic complexes is carried out by one-step condensation in the presence of a suitable lanthanide ion which acts as a template for the macrocycle formation.

Recently, Hu et al. have reported the crystal structures of GdIII, HoIII and LuIII complexes with the macrocyclic ligand derived from 2,6-diformyl-4-methylphenol and 1,5-diamino-3-azapentane (Hu, Chen, Qiu & Pan, 2007; Hu, Qiu, Yuan & Pan, 2007; Hu, Qiu, Zhao & Pan, 2007). Herein we report a new EuIII analogue, synthesized by the same method using 2,6-diformyl-4-chlorophenol instead of 2,6-diformyl-4-methylphenol. The compound is isostructural with the previously reported GdIII and HoIII complexes.

Related literature top

For applications of macrocyclic lanthanide complexes, see: Alexander (1995); Bunzli & Piguet (2002). For related structures, see: Hu, Chen et al. (2007); Hu, Qiu, Yuan & Pan (2007); Hu, Qiu, Zhao & Pan (2007).

Experimental top

1,5-Diamino-3-azapentane (1 mmol) was added dropwise to a methanolic solution (20 ml) of 2,6-diformyl-4-chlorophenol (1 mmol) and Eu(NO3)3.6H2O (0.5 mmol). After refluxing for 5 h, the solvent was removed and the resulting yellow solid was recrystallized from CH3CN to yield yellow block crystals.

Refinement top

All carbon-bound H atoms were generated geometrically (C—H = 0.93–0.97 Å) and included in the refinement as riding with Uiso(H) = 1.2 or 1.5Ueq(C). The H atoms of the N—H group and methanol molecule were located in difference Fourier maps. The former was refined freely, while the latter was constrained to ride on the O atom with Uiso(H) = 1.5Ueq(O). Atoms O10 and O11 in the uncoordinated nitrate and O8 in the coordinate nitrate are modelled as disordered. The N—O distances were restrained to be comparable within the two disorder components (with s.u. 0.005 Å) and the displacement parameters of the disordered atoms were restrained to approximate isotropic behaviour. The C—O distance of the methanol molecule was restrained to 1.40 (1) Å.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular strucure with displacement ellipsoids drawn at the 30% probability level. H atoms are omitted.
[Figure 2] Fig. 2. Coordination polyhedron around the EuIII atom.
[13,27-Dichloro-3,6,9,17,20,23- hexaazatetracyclo[23.3.1.111,15.02,6]triaconta- 1(29),9,11,13,15 (30),16,23,25,27-nonaene-29,30-diol- κ5N17,N20,N23,O29,O30] bis(nitrato-κ2O,O')europium(III) nitrate methanol hemisolvate top
Crystal data top
[Eu(NO3)2(C24H28Cl2N6O2)]NO3·0.5CH4OF000 = 3432
Mr = 857.44Dx = 1.728 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8071 reflections
a = 23.7371 (16) Åθ = 2.6–27.9º
b = 14.3327 (10) ŵ = 2.14 mm−1
c = 19.3880 (13) ÅT = 293 K
β = 91.804 (1)ºBlock, yellow
V = 6592.9 (8) Å30.30 × 0.22 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer		6469 independent reflections
Radiation source: sealed tube5337 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.016
T = 293 Kθmax = 26.0º
φ and ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −28→29
Tmin = 0.58, Tmax = 0.66k = −13→17
18638 measured reflectionsl = −16→23
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)] = 0.032H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.088  w = 1/[σ2(Fo2) + (0.0424P)2 + 14.6115P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
6469 reflectionsΔρmax = 1.37 e Å−3
453 parametersΔρmin = −0.81 e Å−3
62 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Eu(NO3)2(C24H28Cl2N6O2)]NO3·0.5CH4OV = 6592.9 (8) Å3
Mr = 857.44Z = 8
Monoclinic, C2/cMo Kα
a = 23.7371 (16) ŵ = 2.14 mm−1
b = 14.3327 (10) ÅT = 293 K
c = 19.3880 (13) Å0.30 × 0.22 × 0.20 mm
β = 91.804 (1)º
Data collection top
Bruker SMART CCD
diffractometer		6469 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		5337 reflections with I > 2σ(I)
Tmin = 0.58, Tmax = 0.66Rint = 0.016
18638 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03262 restraints
wR(F2) = 0.088H atoms treated by a mixture of
independent and constrained refinement
S = 1.02  w = 1/[σ2(Fo2) + (0.0424P)2 + 14.6115P]
where P = (Fo2 + 2Fc2)/3
6469 reflectionsΔρmax = 1.37 e Å−3
453 parametersΔρmin = −0.81 e Å−3
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*/UeqOcc. (<1)
Eu10.132267 (7)0.505891 (12)0.114103 (11)0.04946 (8)
Cl1−0.09862 (5)0.87749 (10)0.19253 (8)0.0924 (4)
Cl20.44821 (4)0.56791 (11)0.04485 (7)0.0868 (4)
N10.02753 (14)0.4948 (2)0.1406 (2)0.0578 (9)
N20.08955 (15)0.3511 (3)0.0744 (2)0.0720 (11)
H20.10090.30750.10600.086*
N30.20067 (15)0.3992 (3)0.0512 (2)0.0682 (10)
N40.24192 (12)0.7536 (2)0.16799 (16)0.0532 (8)
N50.25996 (14)0.6549 (3)0.25521 (17)0.0677 (10)
H5A0.23670.60780.24290.081*
H5B0.28590.63350.28620.081*
N60.14960 (12)0.8091 (2)0.09364 (17)0.0500 (7)
H60.1482 (19)0.750 (4)0.093 (2)0.075 (15)*
O10.22095 (10)0.5406 (2)0.15231 (14)0.0581 (7)
O20.09634 (10)0.65382 (18)0.12070 (15)0.0543 (6)
C10.05213 (14)0.7012 (3)0.13456 (18)0.0448 (8)
C20.05371 (14)0.7998 (3)0.13119 (19)0.0479 (8)
C30.00702 (16)0.8538 (3)0.1483 (2)0.0576 (10)
H30.00870.91860.14590.069*
C4−0.04138 (16)0.8101 (3)0.1685 (2)0.0602 (10)
C5−0.04490 (15)0.7141 (3)0.1701 (2)0.0584 (10)
H5−0.07830.68610.18310.070*
C60.00017 (14)0.6583 (3)0.15280 (19)0.0497 (9)
C7−0.00850 (15)0.5575 (3)0.1519 (2)0.0576 (10)
H7−0.04470.53700.16070.069*
C80.00742 (19)0.3978 (3)0.1386 (3)0.0761 (14)
H8A−0.03340.39670.13930.091*
H8B0.02210.36420.17870.091*
C90.02697 (18)0.3523 (3)0.0740 (3)0.0811 (15)
H9A0.01270.28890.07120.097*
H9B0.01260.38640.03400.097*
C100.1133 (2)0.3240 (4)0.0092 (3)0.0850 (15)
H10A0.10360.3703−0.02570.102*
H10B0.09740.2647−0.00560.102*
C110.1762 (2)0.3157 (4)0.0168 (3)0.0911 (17)
H11A0.18580.26060.04370.109*
H11B0.19210.3087−0.02840.109*
C120.25325 (19)0.4135 (3)0.0422 (3)0.0697 (12)
H120.27080.37210.01280.084*
C130.28854 (17)0.4860 (3)0.0720 (2)0.0586 (10)
C140.34386 (19)0.4933 (3)0.0490 (2)0.0660 (12)
H140.35670.45060.01700.079*
C150.37933 (16)0.5622 (3)0.0730 (2)0.0625 (11)
C160.36114 (15)0.6265 (3)0.1197 (2)0.0582 (10)
H160.38520.67410.13480.070*
C170.30710 (14)0.6210 (3)0.1445 (2)0.0542 (9)
C180.27015 (14)0.5485 (3)0.1232 (2)0.0520 (9)
C190.28796 (15)0.6941 (3)0.1932 (2)0.0573 (10)
H190.32010.73290.20810.069*
C200.2276 (2)0.7336 (4)0.2848 (2)0.0845 (16)
H20A0.24580.75610.32710.101*
H20B0.18940.71460.29430.101*
C210.22782 (18)0.8080 (4)0.2290 (2)0.0702 (13)
H21A0.19120.83740.22320.084*
H21B0.25600.85550.23920.084*
C220.25275 (15)0.8039 (3)0.1050 (2)0.0584 (10)
H22A0.26380.76000.06980.070*
H22B0.28390.84680.11340.070*
C230.20158 (16)0.8584 (3)0.0787 (2)0.0608 (10)
H23A0.20130.91930.10040.073*
H23B0.20380.86740.02930.073*
C240.10390 (15)0.8487 (3)0.1123 (2)0.0517 (9)
H240.10320.91360.11370.062*
N70.12585 (13)0.6082 (3)−0.01481 (18)0.0570 (8)
O30.09247 (12)0.5410 (2)−0.00393 (16)0.0666 (7)
O40.17132 (10)0.6095 (2)0.02117 (15)0.0602 (7)
O50.11402 (13)0.6698 (3)−0.05529 (18)0.0798 (9)
N80.14009 (18)0.4670 (5)0.2623 (3)0.0941 (16)
O60.13883 (15)0.4020 (3)0.2184 (2)0.0917 (12)
O70.13077 (13)0.5480 (3)0.24185 (17)0.0784 (9)
O80.1559 (4)0.4690 (9)0.3256 (3)0.099 (2)0.543 (12)
O8'0.1383 (5)0.4232 (9)0.3188 (5)0.099 (2)0.457 (12)
N90.36911 (18)0.6104 (3)0.3621 (2)0.0765 (11)
O90.4091 (2)0.5910 (4)0.3993 (3)0.1301 (16)
O100.3339 (3)0.5519 (5)0.3452 (4)0.104 (2)0.687 (7)
O110.3656 (3)0.6888 (3)0.3356 (3)0.0957 (17)0.687 (7)
O10'0.3531 (7)0.5516 (10)0.3194 (7)0.104 (2)0.313 (7)
O11'0.3356 (5)0.6730 (8)0.3750 (7)0.0957 (17)0.313 (7)
C1M0.50000.6209 (14)0.25000.220 (8)
H1MA0.53860.62460.23700.330*0.50
H1MB0.49850.60410.29780.330*0.50
H1MC0.48080.57440.22240.330*0.50
O1M0.4733 (8)0.7024 (13)0.2367 (13)0.295 (11)0.50
H1WD0.44420.73100.24580.442*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu10.03538 (11)0.04471 (12)0.06810 (15)0.00163 (7)−0.00116 (8)0.00535 (8)
Cl10.0600 (7)0.0939 (9)0.1253 (11)0.0351 (6)0.0364 (7)0.0337 (8)
Cl20.0409 (5)0.1263 (11)0.0944 (9)0.0189 (6)0.0194 (5)0.0119 (8)
N10.0387 (17)0.0527 (19)0.082 (2)−0.0089 (14)−0.0029 (16)0.0151 (16)
N20.055 (2)0.052 (2)0.108 (3)0.0004 (16)−0.014 (2)0.002 (2)
N30.059 (2)0.055 (2)0.091 (3)0.0117 (17)−0.0009 (19)−0.0088 (18)
N40.0346 (15)0.069 (2)0.0562 (19)−0.0009 (14)0.0057 (13)−0.0043 (15)
N50.0447 (18)0.104 (3)0.054 (2)0.0002 (18)−0.0010 (15)0.0061 (19)
N60.0378 (15)0.0477 (19)0.065 (2)−0.0017 (14)0.0060 (14)0.0057 (15)
O10.0344 (13)0.0762 (19)0.0637 (17)0.0021 (12)0.0033 (11)−0.0021 (14)
O20.0368 (13)0.0453 (14)0.0814 (19)0.0022 (11)0.0128 (12)0.0044 (13)
C10.0346 (16)0.051 (2)0.049 (2)−0.0001 (14)0.0021 (14)0.0074 (15)
C20.0407 (18)0.050 (2)0.053 (2)0.0026 (15)0.0044 (15)0.0061 (16)
C30.051 (2)0.055 (2)0.067 (3)0.0102 (18)0.0099 (18)0.0108 (19)
C40.0405 (19)0.071 (3)0.070 (3)0.0138 (18)0.0092 (18)0.016 (2)
C50.0366 (18)0.072 (3)0.067 (3)0.0045 (18)0.0066 (17)0.020 (2)
C60.0334 (17)0.060 (2)0.056 (2)−0.0001 (15)0.0029 (15)0.0144 (17)
C70.0327 (18)0.065 (3)0.076 (3)−0.0073 (17)0.0001 (17)0.019 (2)
C80.050 (2)0.058 (3)0.120 (4)−0.010 (2)−0.003 (2)0.021 (3)
C90.054 (2)0.053 (3)0.134 (5)−0.008 (2)−0.018 (3)−0.003 (3)
C100.077 (3)0.062 (3)0.115 (4)0.003 (2)−0.013 (3)−0.023 (3)
C110.077 (3)0.063 (3)0.132 (5)0.009 (3)0.000 (3)−0.032 (3)
C120.061 (3)0.060 (3)0.088 (3)0.022 (2)0.005 (2)−0.007 (2)
C130.046 (2)0.062 (3)0.068 (3)0.0165 (18)0.0005 (18)0.0042 (19)
C140.051 (2)0.080 (3)0.068 (3)0.030 (2)0.006 (2)0.005 (2)
C150.0349 (19)0.085 (3)0.068 (3)0.017 (2)0.0078 (18)0.013 (2)
C160.0341 (18)0.077 (3)0.063 (2)0.0057 (18)0.0001 (16)0.012 (2)
C170.0325 (17)0.077 (3)0.053 (2)0.0058 (17)−0.0008 (15)0.0065 (19)
C180.0350 (17)0.067 (2)0.054 (2)0.0120 (17)0.0006 (15)0.0077 (18)
C190.0350 (18)0.084 (3)0.053 (2)−0.0041 (18)−0.0018 (16)−0.001 (2)
C200.063 (3)0.131 (5)0.061 (3)0.010 (3)0.010 (2)−0.012 (3)
C210.048 (2)0.093 (3)0.071 (3)−0.005 (2)0.011 (2)−0.022 (2)
C220.0402 (19)0.068 (3)0.068 (3)−0.0038 (18)0.0108 (18)0.001 (2)
C230.048 (2)0.051 (2)0.084 (3)−0.0066 (17)0.015 (2)0.007 (2)
C240.045 (2)0.045 (2)0.065 (2)0.0000 (16)0.0040 (17)0.0054 (17)
N70.0444 (18)0.062 (2)0.065 (2)0.0023 (15)0.0068 (15)0.0017 (17)
O30.0598 (17)0.0610 (17)0.078 (2)−0.0098 (15)−0.0092 (14)0.0052 (15)
O40.0374 (13)0.0713 (19)0.0721 (18)0.0014 (12)0.0036 (12)0.0033 (14)
O50.0617 (18)0.089 (2)0.088 (2)−0.0007 (17)−0.0002 (16)0.0328 (19)
N80.058 (2)0.149 (5)0.076 (3)0.031 (3)0.017 (2)0.045 (3)
O60.067 (2)0.087 (3)0.120 (3)0.0060 (19)0.000 (2)0.043 (2)
O70.0608 (19)0.105 (3)0.070 (2)0.0129 (19)0.0101 (15)0.015 (2)
O80.106 (3)0.104 (4)0.087 (3)0.011 (3)0.002 (2)0.020 (3)
O8'0.106 (3)0.104 (4)0.087 (3)0.011 (3)0.002 (2)0.020 (3)
N90.074 (3)0.065 (2)0.089 (3)0.005 (2)−0.027 (2)0.016 (2)
O90.110 (3)0.139 (3)0.138 (3)−0.006 (3)−0.044 (3)0.035 (3)
O100.098 (3)0.094 (3)0.120 (4)−0.015 (3)−0.017 (3)0.029 (3)
O110.100 (3)0.082 (3)0.103 (3)−0.002 (2)−0.026 (2)0.003 (2)
O10'0.098 (3)0.094 (3)0.120 (4)−0.015 (3)−0.017 (3)0.029 (3)
O11'0.100 (3)0.082 (3)0.103 (3)−0.002 (2)−0.026 (2)0.003 (2)
C1M0.218 (9)0.221 (9)0.222 (9)0.0000.009 (5)0.000
O1M0.294 (12)0.290 (12)0.300 (12)−0.013 (5)0.001 (5)0.000 (5)
Geometric parameters (Å, °) top
Eu1—O12.265 (2)C10—H10A0.970
Eu1—O22.290 (2)C10—H10B0.970
Eu1—O32.499 (3)C11—H11A0.970
Eu1—O42.533 (3)C11—H11B0.970
Eu1—O62.513 (4)C12—C131.444 (6)
Eu1—O72.551 (3)C12—H120.930
Eu1—N12.559 (3)C13—C141.403 (6)
Eu1—N22.549 (4)C13—C181.417 (6)
Eu1—N32.566 (4)C14—C151.370 (7)
Cl1—C41.742 (4)C14—H140.930
Cl2—C151.742 (4)C15—C161.371 (6)
N1—C71.264 (5)C16—C171.387 (5)
N1—C81.470 (5)C16—H160.930
N2—C101.452 (7)C17—C181.413 (6)
N2—C91.485 (5)C17—C191.490 (6)
N2—H20.910C19—H190.980
N3—C121.282 (6)C20—C211.519 (7)
N3—C111.480 (6)C20—H20A0.970
N4—C221.448 (5)C20—H20B0.970
N4—C191.459 (5)C21—H21A0.970
N4—C211.465 (5)C21—H21B0.970
N5—C201.489 (6)C22—C231.518 (6)
N5—C191.501 (5)C22—H22A0.970
N5—H5A0.900C22—H22B0.970
N5—H5B0.900C23—H23A0.970
N6—C241.286 (5)C23—H23B0.970
N6—C231.459 (5)C24—H240.930
N6—H60.85 (5)N7—O51.209 (4)
O1—C181.318 (4)N7—O41.267 (4)
O2—C11.286 (4)N7—O31.269 (4)
C1—C21.414 (5)N8—O71.245 (7)
C1—C61.433 (5)N8—O61.262 (7)
C2—C31.401 (5)N8—O8'1.265 (7)
C2—C241.440 (5)N8—O81.273 (6)
C3—C41.376 (5)N9—O91.206 (5)
C3—H30.930N9—O101.221 (4)
C4—C51.380 (6)N9—O11'1.230 (5)
C5—C61.385 (5)N9—O10'1.233 (5)
C5—H50.930N9—O111.238 (4)
C6—C71.459 (6)C1M—O1Mi1.351 (10)
C7—H70.930C1M—O1M1.351 (10)
C8—C91.499 (7)C1M—H1MA0.960
C8—H8A0.970C1M—H1MB0.960
C8—H8B0.970C1M—H1MC0.960
C9—H9A0.970O1M—O1Mi1.35 (4)
C9—H9B0.970O1M—H1WD0.826
C10—C111.501 (7)
O1—Eu1—O297.01 (10)C8—C9—H9B109.7
O1—Eu1—O3125.16 (10)H9A—C9—H9B108.2
O2—Eu1—O374.57 (10)N2—C10—C11110.4 (4)
O1—Eu1—O680.42 (11)N2—C10—H10A109.6
O2—Eu1—O6121.17 (14)C11—C10—H10A109.6
O3—Eu1—O6150.28 (13)N2—C10—H10B109.6
O1—Eu1—O475.31 (9)C11—C10—H10B109.6
O2—Eu1—O469.04 (9)H10A—C10—H10B108.1
O3—Eu1—O450.72 (9)N3—C11—C10110.8 (4)
O6—Eu1—O4154.86 (10)N3—C11—H11A109.5
O1—Eu1—N2130.32 (11)C10—C11—H11A109.5
O2—Eu1—N2132.66 (10)N3—C11—H11B109.5
O3—Eu1—N276.33 (12)C10—C11—H11B109.5
O6—Eu1—N274.98 (15)H11A—C11—H11B108.1
O4—Eu1—N2116.53 (12)N3—C12—C13128.0 (4)
O1—Eu1—O770.82 (10)N3—C12—H12116.0
O2—Eu1—O773.14 (11)C13—C12—H12116.0
O3—Eu1—O7145.58 (11)C14—C13—C18119.2 (4)
O6—Eu1—O750.30 (14)C14—C13—C12117.6 (4)
O4—Eu1—O7124.64 (11)C18—C13—C12123.2 (4)
N2—Eu1—O7118.80 (13)C15—C14—C13121.1 (4)
O1—Eu1—N1147.85 (11)C15—C14—H14119.4
O2—Eu1—N171.36 (9)C13—C14—H14119.4
O3—Eu1—N181.65 (11)C14—C15—C16120.4 (4)
O6—Eu1—N180.66 (11)C14—C15—Cl2120.0 (4)
O4—Eu1—N1123.97 (9)C16—C15—Cl2119.6 (4)
N2—Eu1—N168.09 (12)C15—C16—C17120.3 (4)
O7—Eu1—N177.08 (11)C15—C16—H16119.8
O1—Eu1—N372.00 (11)C17—C16—H16119.8
O2—Eu1—N3145.13 (11)C16—C17—C18120.8 (4)
O3—Eu1—N384.94 (11)C16—C17—C19118.9 (4)
O6—Eu1—N390.28 (14)C18—C17—C19120.2 (3)
O4—Eu1—N376.13 (11)O1—C18—C17119.2 (4)
N2—Eu1—N365.76 (12)O1—C18—C13122.9 (4)
O7—Eu1—N3129.10 (12)C17—C18—C13117.9 (3)
N1—Eu1—N3133.76 (11)N4—C19—C17116.0 (3)
C7—N1—C8117.1 (3)N4—C19—N598.1 (3)
C7—N1—Eu1131.1 (3)C17—C19—N5113.3 (4)
C8—N1—Eu1111.7 (3)N4—C19—H19109.6
C10—N2—C9114.4 (4)C17—C19—H19109.6
C10—N2—Eu1109.5 (3)N5—C19—H19109.6
C9—N2—Eu1112.3 (3)N5—C20—C21104.2 (3)
C10—N2—H2106.7N5—C20—H20A110.9
C9—N2—H2106.7C21—C20—H20A110.9
Eu1—N2—H2106.7N5—C20—H20B110.9
C12—N3—C11115.9 (4)C21—C20—H20B110.9
C12—N3—Eu1127.1 (3)H20A—C20—H20B108.9
C11—N3—Eu1116.8 (3)N4—C21—C20102.0 (4)
C22—N4—C19115.0 (3)N4—C21—H21A111.4
C22—N4—C21117.9 (4)C20—C21—H21A111.4
C19—N4—C21103.2 (3)N4—C21—H21B111.4
C20—N5—C19105.8 (4)C20—C21—H21B111.4
C20—N5—H5A110.6H21A—C21—H21B109.2
C19—N5—H5A110.6N4—C22—C23112.2 (3)
C20—N5—H5B110.6N4—C22—H22A109.2
C19—N5—H5B110.6C23—C22—H22A109.2
H5A—N5—H5B108.7N4—C22—H22B109.2
C24—N6—C23124.6 (4)C23—C22—H22B109.2
C24—N6—H6114 (3)H22A—C22—H22B107.9
C23—N6—H6121 (3)N6—C23—C22110.9 (3)
C18—O1—Eu1134.9 (2)N6—C23—H23A109.5
C1—O2—Eu1144.0 (2)C22—C23—H23A109.5
O2—C1—C2119.7 (3)N6—C23—H23B109.5
O2—C1—C6122.6 (3)C22—C23—H23B109.5
C2—C1—C6117.7 (3)H23A—C23—H23B108.0
C3—C2—C1121.3 (3)N6—C24—C2124.6 (4)
C3—C2—C24117.3 (3)N6—C24—H24117.7
C1—C2—C24121.4 (3)C2—C24—H24117.7
C4—C3—C2119.3 (4)O5—N7—O4121.6 (4)
C4—C3—H3120.3O5—N7—O3121.9 (3)
C2—C3—H3120.3O4—N7—O3116.4 (3)
C3—C4—C5120.8 (4)N7—O3—Eu194.9 (2)
C3—C4—Cl1119.3 (3)N7—O4—Eu193.4 (2)
C5—C4—Cl1119.9 (3)O7—N8—O6118.3 (4)
C4—C5—C6121.5 (4)O7—N8—O8'136.8 (8)
C4—C5—H5119.2O6—N8—O8'102.5 (9)
C6—C5—H5119.2O7—N8—O8109.3 (8)
C5—C6—C1119.3 (4)O6—N8—O8131.8 (7)
C5—C6—C7117.7 (3)N8—O6—Eu196.0 (3)
C1—C6—C7123.0 (3)N8—O7—Eu194.6 (3)
N1—C7—C6127.6 (3)O9—N9—O10121.4 (5)
N1—C7—H7116.2O9—N9—O11'123.3 (8)
C6—C7—H7116.2O9—N9—O10'117.6 (10)
N1—C8—C9109.0 (4)O11'—N9—O10'116.6 (11)
N1—C8—H8A109.9O9—N9—O11119.9 (5)
C9—C8—H8A109.9O10—N9—O11118.4 (5)
N1—C8—H8B109.9O1M—C1M—H1MA110.4
C9—C8—H8B109.9O1M—C1M—H1MB111.7
H8A—C8—H8B108.3H1MA—C1M—H1MB109.5
N2—C9—C8109.6 (4)O1M—C1M—H1MC106.3
N2—C9—H9A109.7H1MA—C1M—H1MC109.5
C8—C9—H9A109.7H1MB—C1M—H1MC109.5
N2—C9—H9B109.7
Symmetry codes: (i) −x+1, y, −z+1/2.
Acknowledgements top

This work is supported by the Natural Science Foundation of Hubei Province (No. 2008CDB094).

references
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