In the crystal structure of the title compound, [Eu
2(C
8H
8NO
2)
6(C
12H
8N
2)
2]
n, the Eu
III atoms are bridged by two tridentate, two bidentate and four mondentate carboxylate groups with an inversion centre between the two Eu
III ions of this dinuclear structural unit. Each Eu atom is nine-coordinated by two 1,10-phenanthroline N atoms and seven O atoms of four anilinoacetate ligands. In the crystal structure, the chains are linked by C—H
N and C—H
O hydrogen bonds into a polymeric ribbon structure.
Supporting information
CCDC reference: 1303498
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.012 Å
- R factor = 0.047
- wR factor = 0.127
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for N5 - C23 .. 8.31 su
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N5
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C21 .. 6.17 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C22 .. 6.00 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Eu1 - O2 .. 6.55 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33
PLAT335_ALERT_2_C Large Benzene C-C Range ....... C4 -C6 0.23 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C4 - C6 ... 1.54 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ?
PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4A ... ?
PLAT420_ALERT_2_C D-H Without Acceptor N5 - H5A ... ?
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 78.00 A 3
Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
19 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
15 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Crystals of the title compound were synthesized using hydrothermal method in a
23 ml Teflon-lined Parr bomb, which was then sealed. Europium (III) nitrate
hexahydrate (206.7 mg, 0.5 mmol), phen (198 mg, 1 mmol), anilinoacetic acid
(292.4 mg, 2 mmol), ammonia (0.5 mol/l, 4 ml) and distilled water (8 g) were
placed into the bomb and sealed. The bomb was then heated under autogenous
pressure up to 453 K over the course of 7 d and allowed to cool at room
temperature for 24 h. Upon opening the bomb, a clear colorless solution was
decanted from small colorless crystals. These crystals were washed with
distilled water followed by ethanol, and allowed to air-dry at room
temperature.
H3A and H4A (for NH) were located in difference syntheses and refined
isotropically [N—H = 0.78 (3) and 0.83 (6) Å, Uiso(H) = 0.07 (1) and
0.08 (2) Å2]. The H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 - 0.97 Å (for CH), and constrained to ride on
their parent atoms, with Uiso(H) = xUeq(C,N), where
x = 1.2 for aromatic and NH H atoms and x = 1.5 for methyl H
atoms.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).
catena-Poly[[tetra-µ-anilinoacetato-bis(1,10-
phenanthroline)dieuropium(III)]-di-µ-anilinoacetato]
top
Crystal data top
[Eu2(C8H8NO2)6(C12H8N2)2] | F(000) = 1576 |
Mr = 1565.26 | Dx = 1.464 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9044 reflections |
a = 19.783 (2) Å | θ = 2.7–26.1° |
b = 8.8013 (14) Å | µ = 1.82 mm−1 |
c = 21.2014 (12) Å | T = 273 K |
β = 105.816 (5)° | Plane, colourless |
V = 3551.8 (7) Å3 | 0.34 × 0.12 × 0.09 mm |
Z = 2 | |
Data collection top
Bruker APEXII area-detector diffractometer | 7520 independent reflections |
Radiation source: fine-focus sealed tube | 4961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ϕ and ω scans | θmax = 27.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −25→24 |
Tmin = 0.581, Tmax = 0.859 | k = −10→11 |
27025 measured reflections | l = −26→26 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0708P)2 + 1.1179P] where P = (Fo2 + 2Fc2)/3 |
7520 reflections | (Δ/σ)max = 0.002 |
411 parameters | Δρmax = 1.49 e Å−3 |
5 restraints | Δρmin = −0.85 e Å−3 |
Crystal data top
[Eu2(C8H8NO2)6(C12H8N2)2] | V = 3551.8 (7) Å3 |
Mr = 1565.26 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 19.783 (2) Å | µ = 1.82 mm−1 |
b = 8.8013 (14) Å | T = 273 K |
c = 21.2014 (12) Å | 0.34 × 0.12 × 0.09 mm |
β = 105.816 (5)° | |
Data collection top
Bruker APEXII area-detector diffractometer | 7520 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4961 reflections with I > 2σ(I) |
Tmin = 0.581, Tmax = 0.859 | Rint = 0.043 |
27025 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 5 restraints |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 1.49 e Å−3 |
7520 reflections | Δρmin = −0.85 e Å−3 |
411 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 | Uiso*/Ueq | |
Eu1 | 0.931209 (13) | 0.19067 (3) | 0.964289 (11) | 0.04106 (11) | |
O1 | 0.84657 (16) | −0.0352 (4) | 0.91894 (16) | 0.0422 (8) | |
O2 | 0.94691 (17) | −0.1382 (4) | 0.97736 (16) | 0.0476 (8) | |
O3 | 0.97044 (17) | 0.0609 (4) | 0.87446 (15) | 0.0452 (8) | |
O4 | 0.93985 (18) | 0.4212 (4) | 1.03389 (15) | 0.0448 (8) | |
O5 | 1.06684 (18) | −0.0828 (4) | 0.92183 (16) | 0.0473 (8) | |
O6 | 1.0076 (2) | 0.6122 (4) | 1.09116 (16) | 0.0539 (9) | |
N1 | 0.7970 (2) | 0.2338 (5) | 0.9672 (2) | 0.0455 (10) | |
N2 | 0.8341 (2) | 0.3067 (4) | 0.8547 (2) | 0.0468 (10) | |
N3 | 1.1191 (2) | −0.0134 (6) | 0.8228 (2) | 0.0469 (11) | |
N5 | 0.7853 (2) | −0.3271 (4) | 0.8984 (2) | 0.0450 (10) | |
H5A | 0.7628 | −0.3417 | 0.8580 | 0.054* | |
N4 | 0.9877 (2) | 0.5262 (5) | 1.20640 (19) | 0.0436 (10) | |
C1 | 0.7784 (3) | 0.1908 (7) | 1.0196 (3) | 0.0620 (16) | |
H1 | 0.8133 | 0.1671 | 1.0576 | 0.074* | |
C2 | 0.7090 (3) | 0.1799 (9) | 1.0198 (4) | 0.083 (2) | |
H2 | 0.6964 | 0.1530 | 1.0575 | 0.100* | |
C3 | 0.6584 (4) | 0.2107 (9) | 0.9612 (5) | 0.092 (3) | |
H3 | 0.6113 | 0.1982 | 0.9599 | 0.110* | |
C4 | 0.6742 (3) | 0.2585 (9) | 0.9055 (4) | 0.077 (2) | |
C5 | 0.7465 (3) | 0.2678 (6) | 0.9087 (3) | 0.0507 (13) | |
C6 | 0.6224 (4) | 0.2954 (11) | 0.8388 (5) | 0.109 (3) | |
H6 | 0.5746 | 0.2829 | 0.8343 | 0.131* | |
C7 | 0.6419 (4) | 0.3435 (10) | 0.7880 (4) | 0.100 (3) | |
H7 | 0.6081 | 0.3710 | 0.7498 | 0.120* | |
C8 | 0.7132 (3) | 0.3537 (8) | 0.7907 (3) | 0.0671 (18) | |
C9 | 0.7661 (3) | 0.3098 (6) | 0.8509 (3) | 0.0499 (13) | |
C10 | 0.7359 (5) | 0.4045 (8) | 0.7374 (3) | 0.087 (2) | |
H10 | 0.7036 | 0.4400 | 0.6998 | 0.104* | |
C11 | 0.8044 (5) | 0.4017 (8) | 0.7407 (3) | 0.080 (2) | |
H11 | 0.8203 | 0.4321 | 0.7053 | 0.096* | |
C12 | 0.8528 (3) | 0.3502 (7) | 0.8007 (3) | 0.0610 (15) | |
H12 | 0.9002 | 0.3468 | 0.8024 | 0.073* | |
C13 | 1.0285 (3) | 0.0026 (6) | 0.8770 (2) | 0.0409 (11) | |
C14 | 1.0524 (3) | 0.0510 (7) | 0.8173 (3) | 0.0512 (13) | |
H14A | 1.0191 | 0.0160 | 0.7775 | 0.061* | |
H14B | 1.0552 | 0.1609 | 0.8156 | 0.061* | |
C15 | 1.1463 (3) | 0.0138 (7) | 0.7702 (3) | 0.0610 (15) | |
C16 | 1.2071 (3) | −0.0572 (9) | 0.7757 (3) | 0.0765 (19) | |
H16 | 1.2269 | −0.1189 | 0.8116 | 0.092* | |
C17 | 1.2400 (4) | −0.0367 (10) | 0.7266 (5) | 0.093 (2) | |
H17 | 1.2830 | −0.0833 | 0.7301 | 0.111* | |
C18 | 1.2100 (5) | 0.0521 (10) | 0.6723 (5) | 0.106 (3) | |
H18 | 1.2330 | 0.0624 | 0.6397 | 0.128* | |
C19 | 1.1477 (5) | 0.1245 (11) | 0.6655 (4) | 0.109 (3) | |
H19 | 1.1278 | 0.1841 | 0.6289 | 0.131* | |
C20 | 1.1147 (4) | 0.1063 (9) | 0.7152 (4) | 0.083 (2) | |
H20 | 1.0722 | 0.1546 | 0.7124 | 0.100* | |
C21 | 0.8840 (3) | −0.1515 (6) | 0.9389 (2) | 0.0431 (12) | |
C22 | 0.8583 (3) | −0.3150 (6) | 0.9197 (3) | 0.0545 (14) | |
H22A | 0.8780 | −0.3501 | 0.8852 | 0.065* | |
H22B | 0.8756 | −0.3809 | 0.9573 | 0.065* | |
C23 | 0.7535 (7) | −0.3143 (10) | 0.9462 (7) | 0.1243 (16) | |
C24 | 0.7846 (6) | −0.2767 (10) | 1.0124 (7) | 0.1243 (16) | |
H24 | 0.8326 | −0.2584 | 1.0277 | 0.149* | |
C25 | 0.7421 (6) | −0.2681 (11) | 1.0536 (7) | 0.1243 (16) | |
H25 | 0.7602 | −0.2451 | 1.0978 | 0.149* | |
C26 | 0.6719 (6) | −0.2946 (10) | 1.0268 (7) | 0.1243 (16) | |
H26 | 0.6431 | −0.2843 | 1.0547 | 0.149* | |
C27 | 0.6385 (6) | −0.3358 (10) | 0.9615 (6) | 0.1243 (16) | |
H27 | 0.5908 | −0.3579 | 0.9476 | 0.149* | |
C28 | 0.6802 (6) | −0.3414 (10) | 0.9198 (6) | 0.1243 (16) | |
H28 | 0.6613 | −0.3623 | 0.8755 | 0.149* | |
C29 | 0.9697 (3) | 0.4996 (6) | 1.0863 (2) | 0.0417 (11) | |
C30 | 0.9484 (3) | 0.4461 (7) | 1.1474 (2) | 0.0542 (14) | |
H30A | 0.8986 | 0.4634 | 1.1408 | 0.065* | |
H30B | 0.9570 | 0.3378 | 1.1533 | 0.065* | |
C31 | 0.9743 (3) | 0.4892 (6) | 1.2657 (2) | 0.0521 (13) | |
C32 | 0.9280 (3) | 0.3784 (9) | 1.2720 (3) | 0.0706 (18) | |
H32 | 0.9027 | 0.3236 | 1.2357 | 0.085* | |
C33 | 0.9196 (5) | 0.3497 (12) | 1.3341 (4) | 0.109 (3) | |
H33 | 0.8893 | 0.2730 | 1.3393 | 0.130* | |
C34 | 0.9573 (5) | 0.4368 (12) | 1.3906 (3) | 0.102 (3) | |
H34 | 0.9497 | 0.4196 | 1.4314 | 0.122* | |
C35 | 1.0033 (4) | 0.5429 (9) | 1.3832 (3) | 0.086 (2) | |
H35 | 1.0284 | 0.5984 | 1.4193 | 0.103* | |
C36 | 1.0139 (3) | 0.5704 (8) | 1.3220 (3) | 0.0705 (17) | |
H36 | 1.0470 | 0.6420 | 1.3177 | 0.085* | |
H4A | 0.959 (3) | 0.596 (6) | 1.204 (3) | 0.08 (2)* | |
H3A | 1.1044 (17) | −0.091 (3) | 0.8091 (16) | 0.07 (1)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Eu1 | 0.04517 (16) | 0.03736 (17) | 0.03679 (15) | −0.00155 (12) | 0.00464 (10) | 0.00065 (11) |
O1 | 0.0382 (17) | 0.0343 (19) | 0.0479 (19) | 0.0005 (15) | 0.0008 (14) | −0.0027 (15) |
O2 | 0.0393 (18) | 0.051 (2) | 0.045 (2) | −0.0022 (16) | 0.0000 (15) | 0.0083 (16) |
O3 | 0.050 (2) | 0.049 (2) | 0.0379 (18) | 0.0054 (17) | 0.0138 (15) | 0.0020 (16) |
O4 | 0.061 (2) | 0.0342 (19) | 0.0396 (18) | −0.0046 (16) | 0.0139 (15) | −0.0048 (15) |
O5 | 0.055 (2) | 0.049 (2) | 0.0406 (19) | 0.0089 (17) | 0.0176 (16) | 0.0107 (16) |
O6 | 0.074 (2) | 0.050 (2) | 0.039 (2) | −0.025 (2) | 0.0186 (17) | −0.0034 (16) |
N1 | 0.042 (2) | 0.040 (2) | 0.049 (3) | 0.0031 (19) | 0.0033 (19) | −0.0093 (19) |
N2 | 0.057 (3) | 0.039 (2) | 0.036 (2) | 0.003 (2) | −0.0015 (18) | 0.0002 (18) |
N3 | 0.047 (2) | 0.054 (3) | 0.045 (3) | 0.006 (2) | 0.022 (2) | 0.010 (2) |
N5 | 0.037 (2) | 0.032 (2) | 0.056 (3) | −0.0128 (17) | −0.0045 (18) | −0.0075 (18) |
N4 | 0.061 (3) | 0.043 (3) | 0.028 (2) | −0.021 (2) | 0.0151 (19) | −0.0060 (18) |
C1 | 0.051 (3) | 0.077 (5) | 0.058 (4) | 0.008 (3) | 0.015 (3) | −0.002 (3) |
C2 | 0.051 (4) | 0.116 (7) | 0.087 (5) | 0.005 (4) | 0.027 (4) | −0.010 (4) |
C3 | 0.043 (4) | 0.109 (7) | 0.122 (7) | −0.006 (4) | 0.020 (4) | −0.014 (5) |
C4 | 0.046 (3) | 0.085 (5) | 0.083 (5) | 0.008 (3) | −0.009 (3) | −0.021 (4) |
C5 | 0.048 (3) | 0.035 (3) | 0.062 (4) | 0.007 (2) | 0.002 (3) | −0.011 (2) |
C6 | 0.049 (4) | 0.146 (9) | 0.107 (7) | 0.017 (5) | −0.021 (4) | −0.027 (6) |
C7 | 0.075 (5) | 0.115 (7) | 0.078 (5) | 0.039 (5) | −0.031 (4) | −0.015 (5) |
C8 | 0.067 (4) | 0.068 (4) | 0.046 (4) | 0.018 (3) | −0.018 (3) | −0.010 (3) |
C9 | 0.054 (3) | 0.033 (3) | 0.050 (3) | 0.006 (2) | −0.009 (2) | −0.003 (2) |
C10 | 0.113 (6) | 0.070 (5) | 0.050 (4) | 0.018 (4) | −0.024 (4) | −0.001 (3) |
C11 | 0.116 (6) | 0.074 (5) | 0.038 (3) | −0.002 (4) | 0.002 (3) | 0.009 (3) |
C12 | 0.075 (4) | 0.055 (4) | 0.046 (3) | −0.002 (3) | 0.004 (3) | 0.010 (3) |
C13 | 0.050 (3) | 0.034 (3) | 0.038 (3) | −0.008 (2) | 0.011 (2) | −0.004 (2) |
C14 | 0.060 (3) | 0.051 (3) | 0.045 (3) | 0.007 (3) | 0.018 (2) | 0.011 (2) |
C15 | 0.064 (4) | 0.069 (4) | 0.057 (4) | −0.009 (3) | 0.029 (3) | 0.000 (3) |
C16 | 0.072 (4) | 0.094 (5) | 0.074 (4) | 0.005 (4) | 0.037 (4) | 0.001 (4) |
C17 | 0.082 (5) | 0.097 (6) | 0.117 (6) | −0.008 (5) | 0.057 (5) | −0.010 (5) |
C18 | 0.138 (8) | 0.085 (6) | 0.133 (8) | −0.018 (6) | 0.101 (7) | −0.001 (6) |
C19 | 0.148 (8) | 0.115 (7) | 0.092 (6) | 0.021 (6) | 0.078 (6) | 0.035 (5) |
C20 | 0.096 (5) | 0.089 (5) | 0.082 (5) | 0.004 (4) | 0.056 (4) | 0.023 (4) |
C21 | 0.043 (3) | 0.052 (3) | 0.031 (2) | −0.007 (2) | 0.004 (2) | −0.005 (2) |
C22 | 0.057 (3) | 0.043 (3) | 0.059 (3) | 0.003 (3) | 0.007 (3) | −0.008 (3) |
C23 | 0.132 (4) | 0.090 (3) | 0.174 (5) | 0.015 (3) | 0.082 (4) | 0.031 (3) |
C24 | 0.132 (4) | 0.090 (3) | 0.174 (5) | 0.015 (3) | 0.082 (4) | 0.031 (3) |
C25 | 0.132 (4) | 0.090 (3) | 0.174 (5) | 0.015 (3) | 0.082 (4) | 0.031 (3) |
C26 | 0.132 (4) | 0.090 (3) | 0.174 (5) | 0.015 (3) | 0.082 (4) | 0.031 (3) |
C27 | 0.132 (4) | 0.090 (3) | 0.174 (5) | 0.015 (3) | 0.082 (4) | 0.031 (3) |
C28 | 0.132 (4) | 0.090 (3) | 0.174 (5) | 0.015 (3) | 0.082 (4) | 0.031 (3) |
C29 | 0.055 (3) | 0.032 (3) | 0.039 (3) | −0.001 (2) | 0.013 (2) | 0.004 (2) |
C30 | 0.070 (3) | 0.054 (3) | 0.040 (3) | −0.021 (3) | 0.017 (2) | −0.007 (2) |
C31 | 0.068 (3) | 0.054 (3) | 0.034 (3) | −0.002 (3) | 0.014 (2) | 0.004 (2) |
C32 | 0.071 (4) | 0.094 (5) | 0.049 (3) | −0.031 (4) | 0.020 (3) | −0.002 (3) |
C33 | 0.122 (7) | 0.142 (8) | 0.078 (5) | −0.050 (6) | 0.053 (5) | 0.001 (5) |
C34 | 0.114 (6) | 0.151 (8) | 0.047 (4) | −0.030 (6) | 0.035 (4) | 0.003 (5) |
C35 | 0.106 (5) | 0.106 (6) | 0.041 (3) | −0.021 (5) | 0.013 (3) | −0.010 (4) |
C36 | 0.082 (4) | 0.075 (5) | 0.051 (3) | −0.019 (4) | 0.013 (3) | −0.010 (3) |
Geometric parameters (Å, º) top
Eu1—O1 | 2.608 (3) | C10—C11 | 1.337 (10) |
Eu1—O2i | 2.435 (3) | C10—H10 | 0.9300 |
Eu1—O2 | 2.916 (4) | C11—C12 | 1.441 (8) |
Eu1—O3 | 2.518 (3) | C11—H11 | 0.9300 |
Eu1—O4 | 2.487 (3) | C12—H12 | 0.9300 |
Eu1—O5i | 2.585 (3) | C13—C14 | 1.528 (7) |
Eu1—O6ii | 2.576 (3) | C14—H14A | 0.9700 |
Eu1—N1 | 2.700 (4) | C14—H14B | 0.9700 |
Eu1—N2 | 2.776 (4) | C15—C16 | 1.332 (9) |
Eu1—Eu1i | 4.3265 (7) | C15—C20 | 1.420 (9) |
O1—C21 | 1.267 (6) | C16—C17 | 1.382 (10) |
O2—C21 | 1.293 (6) | C16—H16 | 0.9300 |
O2—Eu1i | 2.435 (3) | C17—C18 | 1.384 (12) |
O3—C13 | 1.245 (6) | C17—H17 | 0.9300 |
O4—C29 | 1.304 (6) | C18—C19 | 1.361 (12) |
O5—C13 | 1.284 (6) | C18—H18 | 0.9300 |
O5—Eu1i | 2.585 (3) | C19—C20 | 1.391 (9) |
O6—C29 | 1.230 (6) | C19—H19 | 0.9300 |
O6—Eu1ii | 2.576 (3) | C20—H20 | 0.9300 |
N1—C1 | 1.317 (7) | C21—C22 | 1.544 (7) |
N1—C5 | 1.395 (7) | C22—H22A | 0.9700 |
N2—C9 | 1.325 (7) | C22—H22B | 0.9700 |
N2—C12 | 1.350 (7) | C23—C24 | 1.410 (17) |
N3—C15 | 1.386 (7) | C23—C28 | 1.426 (16) |
N3—C14 | 1.411 (6) | C24—C25 | 1.368 (14) |
N3—H3A | 0.78 (3) | C24—H24 | 0.9300 |
N5—C23 | 1.337 (12) | C25—C26 | 1.371 (16) |
N5—C22 | 1.393 (7) | C25—H25 | 0.9300 |
N5—H5A | 0.8600 | C26—C27 | 1.410 (16) |
N4—C31 | 1.392 (6) | C26—H26 | 0.9300 |
N4—C30 | 1.461 (6) | C27—C28 | 1.364 (13) |
N4—H4A | 0.83 (6) | C27—H27 | 0.9300 |
C1—C2 | 1.379 (9) | C28—H28 | 0.9300 |
C1—H1 | 0.9300 | C29—C30 | 1.541 (7) |
C2—C3 | 1.393 (12) | C30—H30A | 0.9700 |
C2—H2 | 0.9300 | C30—H30B | 0.9700 |
C3—C4 | 1.369 (12) | C31—C32 | 1.369 (8) |
C3—H3 | 0.9300 | C31—C36 | 1.428 (8) |
C4—C5 | 1.414 (9) | C32—C33 | 1.394 (9) |
C4—C6 | 1.538 (11) | C32—H32 | 0.9300 |
C5—C9 | 1.431 (8) | C33—C34 | 1.445 (11) |
C6—C7 | 1.309 (13) | C33—H33 | 0.9300 |
C6—H6 | 0.9300 | C34—C35 | 1.344 (10) |
C7—C8 | 1.398 (11) | C34—H34 | 0.9300 |
C7—H7 | 0.9300 | C35—C36 | 1.390 (9) |
C8—C10 | 1.399 (10) | C35—H35 | 0.9300 |
C8—C9 | 1.466 (7) | C36—H36 | 0.9300 |
| | | |
O1—Eu1—O2 | 47.12 (9) | C5—C9—C8 | 121.2 (5) |
O1—Eu1—O3 | 71.02 (11) | C11—C10—C8 | 119.7 (6) |
O1—Eu1—O4 | 140.70 (11) | C11—C10—H10 | 120.1 |
O2—Eu1—O3 | 64.84 (10) | C8—C10—H10 | 120.1 |
O2—Eu1—O4 | 139.91 (10) | C10—C11—C12 | 118.2 (7) |
O3—Eu1—O4 | 146.44 (11) | C10—C11—H11 | 120.9 |
O1—Eu1—N1 | 65.09 (12) | C12—C11—H11 | 120.9 |
O1—Eu1—N2 | 75.12 (11) | N2—C12—C11 | 124.6 (6) |
O2—Eu1—N1 | 102.55 (12) | N2—C12—H12 | 117.7 |
O2—Eu1—N2 | 118.44 (11) | C11—C12—H12 | 117.7 |
O3—Eu1—N1 | 126.06 (12) | O3—C13—O5 | 128.7 (4) |
O3—Eu1—N2 | 79.59 (12) | O3—C13—C14 | 109.8 (4) |
O4—Eu1—N1 | 77.35 (12) | O5—C13—C14 | 121.4 (4) |
O4—Eu1—N2 | 96.70 (11) | N3—C14—C13 | 108.3 (4) |
N1—Eu1—N2 | 60.42 (14) | N3—C14—H14A | 110.0 |
O2i—Eu1—O4 | 87.41 (12) | C13—C14—H14A | 110.0 |
O2i—Eu1—O3 | 80.31 (11) | N3—C14—H14B | 110.0 |
O2i—Eu1—O6ii | 80.57 (12) | C13—C14—H14B | 110.0 |
O4—Eu1—O6ii | 75.90 (11) | H14A—C14—H14B | 108.4 |
O3—Eu1—O6ii | 71.35 (11) | C16—C15—N3 | 112.8 (6) |
O2i—Eu1—O5i | 72.25 (11) | C16—C15—C20 | 121.8 (6) |
O4—Eu1—O5i | 76.37 (11) | N3—C15—C20 | 125.4 (6) |
O3—Eu1—O5i | 127.64 (11) | C15—C16—C17 | 118.1 (7) |
O6ii—Eu1—O5i | 141.68 (11) | C15—C16—H16 | 120.9 |
O2i—Eu1—O1 | 119.34 (12) | C17—C16—H16 | 120.9 |
O6ii—Eu1—O1 | 132.82 (11) | C16—C17—C18 | 121.2 (7) |
O5i—Eu1—O1 | 84.78 (11) | C16—C17—H17 | 119.4 |
O2i—Eu1—N1 | 149.20 (12) | C18—C17—H17 | 119.4 |
O6ii—Eu1—N1 | 120.21 (14) | C19—C18—C17 | 121.5 (7) |
O5i—Eu1—N1 | 78.16 (12) | C19—C18—H18 | 119.2 |
O2i—Eu1—N2 | 149.19 (13) | C17—C18—H18 | 119.2 |
O6ii—Eu1—N2 | 70.99 (13) | C18—C19—C20 | 117.6 (8) |
O5i—Eu1—N2 | 138.42 (12) | C18—C19—H19 | 121.2 |
O2i—Eu1—O2 | 72.45 (13) | C20—C19—H19 | 121.2 |
O6ii—Eu1—O2 | 131.37 (11) | C19—C20—C15 | 119.7 (7) |
O5i—Eu1—O2 | 64.69 (10) | C19—C20—H20 | 120.1 |
O2i—Eu1—Eu1i | 39.99 (9) | C15—C20—H20 | 120.1 |
O4—Eu1—Eu1i | 119.35 (8) | O1—C21—O2 | 120.8 (5) |
O3—Eu1—Eu1i | 67.59 (8) | O1—C21—C22 | 122.9 (4) |
O6ii—Eu1—Eu1i | 110.69 (9) | O2—C21—C22 | 116.3 (5) |
O5i—Eu1—Eu1i | 62.63 (7) | N5—C22—C21 | 113.3 (4) |
O1—Eu1—Eu1i | 79.46 (7) | N5—C22—H22A | 108.9 |
N1—Eu1—Eu1i | 129.05 (10) | C21—C22—H22A | 108.9 |
N2—Eu1—Eu1i | 143.56 (8) | N5—C22—H22B | 108.9 |
O2—Eu1—Eu1i | 32.46 (6) | C21—C22—H22B | 108.9 |
C21—O1—Eu1 | 103.5 (3) | H22A—C22—H22B | 107.7 |
C21—O2—Eu1i | 162.2 (4) | N5—C23—C24 | 127.4 (11) |
C21—O2—Eu1 | 88.3 (3) | N5—C23—C28 | 109.1 (12) |
Eu1i—O2—Eu1 | 107.55 (13) | C24—C23—C28 | 123.5 (11) |
C13—O3—Eu1 | 128.7 (3) | C25—C24—C23 | 118.1 (12) |
C29—O4—Eu1 | 151.5 (3) | C25—C24—H24 | 121.0 |
C13—O5—Eu1i | 139.5 (3) | C23—C24—H24 | 121.0 |
C29—O6—Eu1ii | 148.9 (3) | C24—C25—C26 | 117.2 (13) |
C1—N1—C5 | 120.9 (5) | C24—C25—H25 | 121.4 |
C1—N1—Eu1 | 118.7 (4) | C26—C25—H25 | 121.4 |
C5—N1—Eu1 | 118.7 (3) | C25—C26—C27 | 126.9 (11) |
C9—N2—C12 | 116.9 (5) | C25—C26—H26 | 116.5 |
C9—N2—Eu1 | 121.1 (3) | C27—C26—H26 | 116.5 |
C12—N2—Eu1 | 121.8 (4) | C28—C27—C26 | 116.2 (12) |
C15—N3—C14 | 115.1 (4) | C28—C27—H27 | 121.9 |
C15—N3—H3A | 92 (3) | C26—C27—H27 | 121.9 |
C14—N3—H3A | 95 (3) | C27—C28—C23 | 118.0 (13) |
C23—N5—C22 | 114.0 (7) | C27—C28—H28 | 121.0 |
C23—N5—H5A | 123.0 | C23—C28—H28 | 121.0 |
C22—N5—H5A | 123.0 | O6—C29—O4 | 128.5 (4) |
C31—N4—C30 | 118.2 (4) | O6—C29—C30 | 118.4 (4) |
C31—N4—H4A | 86 (5) | O4—C29—C30 | 113.0 (4) |
C30—N4—H4A | 96 (5) | N4—C30—C29 | 111.7 (4) |
N1—C1—C2 | 122.0 (6) | N4—C30—H30A | 109.3 |
N1—C1—H1 | 119.0 | C29—C30—H30A | 109.3 |
C2—C1—H1 | 119.0 | N4—C30—H30B | 109.3 |
C1—C2—C3 | 117.2 (7) | C29—C30—H30B | 109.3 |
C1—C2—H2 | 121.4 | H30A—C30—H30B | 107.9 |
C3—C2—H2 | 121.4 | C32—C31—N4 | 123.5 (5) |
C4—C3—C2 | 123.5 (6) | C32—C31—C36 | 120.3 (5) |
C4—C3—H3 | 118.3 | N4—C31—C36 | 116.2 (5) |
C2—C3—H3 | 118.3 | C32—C31—H4A | 122 (3) |
C3—C4—C5 | 116.2 (6) | C36—C31—H4A | 109 (2) |
C3—C4—C6 | 127.3 (7) | C31—C32—C33 | 118.4 (6) |
C5—C4—C6 | 116.4 (8) | C31—C32—H32 | 120.8 |
N1—C5—C4 | 120.0 (6) | C33—C32—H32 | 120.8 |
N1—C5—C9 | 121.3 (5) | C32—C33—C34 | 121.3 (7) |
C4—C5—C9 | 118.6 (6) | C32—C33—H33 | 119.4 |
C7—C6—C4 | 123.5 (8) | C34—C33—H33 | 119.4 |
C7—C6—H6 | 118.2 | C35—C34—C33 | 119.0 (6) |
C4—C6—H6 | 118.2 | C35—C34—H34 | 120.5 |
C6—C7—C8 | 120.5 (7) | C33—C34—H34 | 120.5 |
C6—C7—H7 | 119.8 | C34—C35—C36 | 120.6 (7) |
C8—C7—H7 | 119.8 | C34—C35—H35 | 119.7 |
C7—C8—C10 | 122.0 (7) | C36—C35—H35 | 119.7 |
C7—C8—C9 | 119.5 (7) | C35—C36—C31 | 120.3 (6) |
C10—C8—C9 | 118.5 (6) | C35—C36—H36 | 119.8 |
N2—C9—C5 | 116.8 (4) | C31—C36—H36 | 119.8 |
N2—C9—C8 | 122.0 (6) | | |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22B···O4iii | 0.97 | 2.48 | 3.424 (7) | 164 |
C12—H12···N4ii | 0.93 | 2.53 | 3.380 (8) | 151 |
C12—H12···O6ii | 0.93 | 2.51 | 3.089 (7) | 121 |
C10—H10···O1iv | 0.93 | 2.45 | 3.314 (7) | 154 |
C1—H1···O5i | 0.93 | 2.41 | 3.121 (7) | 134 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+3/2. |
Experimental details
Crystal data |
Chemical formula | [Eu2(C8H8NO2)6(C12H8N2)2] |
Mr | 1565.26 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 273 |
a, b, c (Å) | 19.783 (2), 8.8013 (14), 21.2014 (12) |
β (°) | 105.816 (5) |
V (Å3) | 3551.8 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.82 |
Crystal size (mm) | 0.34 × 0.12 × 0.09 |
|
Data collection |
Diffractometer | Bruker APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.581, 0.859 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27025, 7520, 4961 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.638 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.127, 1.02 |
No. of reflections | 7520 |
No. of parameters | 411 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.49, −0.85 |
Selected geometric parameters (Å, º) topEu1—O1 | 2.608 (3) | Eu1—O5i | 2.585 (3) |
Eu1—O2i | 2.435 (3) | Eu1—O6ii | 2.576 (3) |
Eu1—O2 | 2.916 (4) | Eu1—N1 | 2.700 (4) |
Eu1—O3 | 2.518 (3) | Eu1—N2 | 2.776 (4) |
Eu1—O4 | 2.487 (3) | | |
| | | |
O1—Eu1—O2 | 47.12 (9) | O2—Eu1—N1 | 102.55 (12) |
O1—Eu1—O3 | 71.02 (11) | O2—Eu1—N2 | 118.44 (11) |
O1—Eu1—O4 | 140.70 (11) | O3—Eu1—N1 | 126.06 (12) |
O2—Eu1—O3 | 64.84 (10) | O3—Eu1—N2 | 79.59 (12) |
O2—Eu1—O4 | 139.91 (10) | O4—Eu1—N1 | 77.35 (12) |
O3—Eu1—O4 | 146.44 (11) | O4—Eu1—N2 | 96.70 (11) |
O1—Eu1—N1 | 65.09 (12) | N1—Eu1—N2 | 60.42 (14) |
O1—Eu1—N2 | 75.12 (11) | | |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22B···O4iii | 0.97 | 2.48 | 3.424 (7) | 164 |
C12—H12···N4ii | 0.93 | 2.53 | 3.380 (8) | 151 |
C12—H12···O6ii | 0.93 | 2.51 | 3.089 (7) | 121 |
C10—H10···O1iv | 0.93 | 2.45 | 3.314 (7) | 154 |
C1—H1···O5i | 0.93 | 2.41 | 3.121 (7) | 134 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+3/2. |
The crystal structure of [RE2(C8H8NO2)6(C12H8N2)2]n (RE = Sm, Nd and La), (II), have previously been reported (Zhong et al., 2007a,b,c). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II). We report herein the crystal structure of (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The title compound, [Eu2(C8H8NO2)6(C12H8N2)2]n, which are bridged by two terdentate, two bidentate and four mondentate carboxyl groups with an inversion centre between the two EuIII ions. Each Eu atom is nine-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and seven O atoms of four anilinoacetate ligands (Table 1). The Eu—O and Eu bonds are in the range of [2.435 (3)–2.916 (4) Å] and [2.700 (4) to 2.776 (4) Å], respectively, as in (II).
In the crystal structure, C—H···N and C—H···O hydrogen bonds (Fig. 2 and Table 2) seem to be effective in the stabilization of the structure, resulting in the formation of a supramolecular network structure, as in (II).
The four compounds, (I) and (II), are isostructural.