Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961901060X/fn3316sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961901060X/fn3316Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S205322961901060X/fn3316sup3.pdf |
CCDC reference: 1943541
Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Eu(C20H17O8)3(CH4O)3] | Dx = 1.433 Mg m−3 |
Mr = 1404.09 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3 | Cell parameters from 9844 reflections |
a = 27.194 (3) Å | θ = 2.6–24.6° |
c = 7.6221 (8) Å | µ = 1.05 mm−1 |
V = 4881.6 (11) Å3 | T = 298 K |
Z = 3 | Prismatic, colorless |
F(000) = 2160 | 0.20 × 0.10 × 0.10 mm |
Bruker APEXII CCD diffractometer | 3375 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.064 |
Absorption correction: multi-scan | θmax = 24.7°, θmin = 2.6° |
Tmin = 0.882, Tmax = 0.901 | h = −31→29 |
16219 measured reflections | k = −30→31 |
3630 independent reflections | l = −8→8 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0338P)2 + 0.6232P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.52 e Å−3 |
3630 reflections | Δρmin = −0.40 e Å−3 |
283 parameters | Absolute structure: Flack x determined using 1387 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
3 restraints | Absolute structure parameter: 0.029 (8) |
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. Single-crystal X-ray diffraction patterns for (I) were measured on a Bruker SMART APEXII diffractometer with a CCD area detector and Mo Kα radiation λ = 0.71073 Å) at room temperature. The multi-scan program SADABS was used for absorption correction (Sheldrick. 2008). The structures were solved by direct methods and refined by the full-matrix least squares method on F2 using the SHELXS-2014 (Sheldrick. 2015). All the non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
Eu1 | 0.666667 | 0.333333 | −0.08423 (6) | 0.02579 (18) | |
O1 | 0.7080 (2) | 0.4067 (2) | 0.1191 (6) | 0.0477 (14) | |
O2 | 0.7547 (2) | 0.4981 (2) | 0.0506 (7) | 0.0505 (15) | |
O3 | 0.7130 (2) | 0.4055 (2) | −0.2990 (6) | 0.0419 (13) | |
O4 | 0.7278 (3) | 0.4923 (2) | 0.7373 (7) | 0.0560 (17) | |
H4 | 0.731 (5) | 0.493 (4) | 0.844 (3) | 0.084* | |
O5 | 0.7905 (3) | 0.5271 (3) | 0.3816 (7) | 0.0415 (16) | |
O6 | 0.8616 (3) | 0.5203 (3) | 0.2577 (9) | 0.073 (2) | |
O7 | 0.6817 (2) | 0.4877 (2) | 0.4171 (6) | 0.0367 (12) | |
O8 | 0.6011 (3) | 0.4288 (3) | 0.5527 (10) | 0.072 (2) | |
O9 | 0.7760 (3) | 0.3811 (3) | −0.0988 (8) | 0.0625 (17) | |
H9A | 0.797 (4) | 0.398 (5) | −0.189 (10) | 0.094* | |
C1 | 0.7380 (3) | 0.4573 (4) | 0.1532 (10) | 0.0354 (18) | |
C2 | 0.7544 (4) | 0.4691 (4) | 0.3461 (10) | 0.034 (2) | |
H2 | 0.773322 | 0.448064 | 0.381340 | 0.041* | |
C3 | 0.7024 (3) | 0.4501 (3) | 0.4566 (8) | 0.0353 (18) | |
H3 | 0.673754 | 0.411712 | 0.420119 | 0.042* | |
C4 | 0.7153 (3) | 0.4486 (3) | 0.6489 (8) | 0.0331 (18) | |
C5 | 0.8459 (5) | 0.5496 (4) | 0.3239 (13) | 0.048 (2) | |
C6 | 0.8790 (4) | 0.6090 (4) | 0.3589 (12) | 0.059 (2) | |
C7 | 0.9327 (5) | 0.6388 (4) | 0.2902 (13) | 0.082 (3) | |
H7 | 0.945518 | 0.620468 | 0.215665 | 0.098* | |
C8 | 0.9674 (5) | 0.6942 (5) | 0.3289 (15) | 0.089 (4) | |
H8 | 1.004235 | 0.712905 | 0.284858 | 0.107* | |
C9 | 0.9495 (5) | 0.7229 (4) | 0.4305 (14) | 0.070 (3) | |
C10 | 0.8955 (6) | 0.6935 (6) | 0.4989 (17) | 0.086 (4) | |
H10 | 0.882831 | 0.712150 | 0.572395 | 0.103* | |
C11 | 0.8600 (5) | 0.6371 (5) | 0.4609 (17) | 0.065 (3) | |
H11 | 0.823158 | 0.618259 | 0.504702 | 0.078* | |
C12 | 0.9885 (5) | 0.7856 (5) | 0.4682 (17) | 0.101 (4) | |
H12A | 0.994552 | 0.807012 | 0.362268 | 0.121* | |
H12B | 1.024278 | 0.791534 | 0.511087 | 0.121* | |
H12C | 0.971435 | 0.797943 | 0.554938 | 0.121* | |
C13 | 0.6286 (5) | 0.4718 (5) | 0.4678 (13) | 0.047 (3) | |
C14 | 0.6102 (4) | 0.5102 (5) | 0.4034 (13) | 0.052 (2) | |
C15 | 0.6470 (5) | 0.5604 (5) | 0.3258 (13) | 0.068 (3) | |
H15 | 0.685211 | 0.571486 | 0.316281 | 0.081* | |
C16 | 0.6275 (6) | 0.5951 (5) | 0.2609 (15) | 0.095 (4) | |
H16 | 0.653215 | 0.629653 | 0.210136 | 0.114* | |
C17 | 0.5720 (7) | 0.5802 (7) | 0.2694 (19) | 0.098 (5) | |
C18 | 0.5362 (8) | 0.5294 (11) | 0.350 (3) | 0.130 (8) | |
H18 | 0.497802 | 0.517792 | 0.358438 | 0.156* | |
C19 | 0.5545 (6) | 0.4964 (7) | 0.4169 (18) | 0.097 (4) | |
H19 | 0.528955 | 0.463095 | 0.474216 | 0.117* | |
C20 | 0.5518 (8) | 0.6182 (8) | 0.194 (2) | 0.164 (8) | |
H20A | 0.577467 | 0.656823 | 0.227055 | 0.197* | |
H20B | 0.514527 | 0.606830 | 0.237755 | 0.197* | |
H20C | 0.550474 | 0.615198 | 0.068075 | 0.197* | |
C21 | 0.8217 (4) | 0.3927 (5) | 0.0165 (15) | 0.079 (3) | |
H21A | 0.837549 | 0.430588 | 0.061821 | 0.095* | |
H21B | 0.850467 | 0.389324 | −0.046426 | 0.095* | |
H21C | 0.808007 | 0.366095 | 0.111812 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Eu1 | 0.0309 (2) | 0.0309 (2) | 0.0156 (2) | 0.01543 (12) | 0.000 | 0.000 |
O1 | 0.062 (4) | 0.040 (4) | 0.028 (3) | 0.016 (3) | −0.001 (2) | −0.015 (2) |
O2 | 0.069 (4) | 0.042 (3) | 0.025 (3) | 0.016 (3) | −0.003 (3) | 0.002 (3) |
O3 | 0.056 (4) | 0.038 (3) | 0.030 (3) | 0.023 (3) | 0.011 (2) | 0.014 (2) |
O4 | 0.097 (5) | 0.047 (4) | 0.020 (3) | 0.033 (4) | −0.009 (3) | −0.002 (3) |
O5 | 0.048 (4) | 0.041 (4) | 0.029 (3) | 0.018 (4) | 0.004 (3) | −0.004 (3) |
O6 | 0.066 (5) | 0.074 (5) | 0.076 (5) | 0.031 (4) | 0.017 (4) | −0.005 (4) |
O7 | 0.039 (3) | 0.044 (3) | 0.030 (3) | 0.023 (3) | −0.001 (2) | 0.004 (2) |
O8 | 0.063 (5) | 0.074 (5) | 0.075 (5) | 0.030 (4) | 0.021 (4) | 0.022 (5) |
O9 | 0.050 (4) | 0.080 (5) | 0.047 (4) | 0.025 (4) | 0.002 (3) | 0.006 (3) |
C1 | 0.039 (5) | 0.037 (5) | 0.029 (4) | 0.018 (4) | −0.004 (4) | −0.010 (4) |
C2 | 0.043 (5) | 0.034 (5) | 0.024 (4) | 0.019 (5) | 0.002 (4) | −0.002 (3) |
C3 | 0.051 (5) | 0.036 (5) | 0.021 (3) | 0.023 (4) | −0.005 (3) | −0.003 (3) |
C4 | 0.047 (5) | 0.026 (4) | 0.021 (4) | 0.014 (4) | 0.008 (3) | 0.003 (3) |
C5 | 0.064 (7) | 0.041 (6) | 0.036 (5) | 0.022 (6) | −0.003 (5) | −0.003 (5) |
C6 | 0.062 (7) | 0.056 (7) | 0.046 (5) | 0.020 (6) | 0.003 (5) | −0.003 (5) |
C7 | 0.078 (8) | 0.060 (7) | 0.073 (7) | 0.008 (6) | 0.025 (6) | −0.002 (5) |
C8 | 0.087 (8) | 0.058 (7) | 0.090 (8) | 0.013 (7) | 0.026 (7) | 0.000 (6) |
C9 | 0.078 (8) | 0.044 (6) | 0.071 (7) | 0.018 (6) | 0.005 (6) | 0.003 (5) |
C10 | 0.091 (11) | 0.071 (10) | 0.090 (9) | 0.036 (9) | 0.011 (8) | −0.023 (8) |
C11 | 0.054 (7) | 0.042 (8) | 0.088 (9) | 0.016 (7) | −0.005 (6) | −0.007 (7) |
C12 | 0.094 (9) | 0.063 (8) | 0.108 (9) | 0.011 (7) | 0.001 (7) | −0.017 (7) |
C13 | 0.050 (7) | 0.060 (8) | 0.033 (5) | 0.028 (6) | −0.002 (5) | −0.001 (5) |
C14 | 0.052 (7) | 0.066 (8) | 0.049 (6) | 0.038 (6) | −0.006 (5) | −0.002 (5) |
C15 | 0.067 (7) | 0.074 (8) | 0.079 (7) | 0.048 (7) | −0.003 (6) | 0.009 (6) |
C16 | 0.103 (10) | 0.110 (10) | 0.110 (10) | 0.081 (9) | 0.014 (8) | 0.029 (8) |
C17 | 0.101 (12) | 0.138 (14) | 0.099 (10) | 0.093 (12) | −0.009 (9) | 0.003 (9) |
C18 | 0.082 (13) | 0.22 (2) | 0.141 (14) | 0.116 (15) | 0.011 (10) | 0.034 (15) |
C19 | 0.077 (10) | 0.131 (14) | 0.103 (10) | 0.066 (10) | 0.012 (7) | 0.025 (9) |
C20 | 0.183 (17) | 0.25 (2) | 0.167 (16) | 0.186 (17) | −0.027 (13) | 0.012 (14) |
C21 | 0.063 (7) | 0.086 (8) | 0.079 (8) | 0.030 (7) | −0.016 (6) | 0.012 (7) |
Eu1—O1i | 2.324 (5) | C7—C8 | 1.352 (14) |
Eu1—O1ii | 2.324 (5) | C7—H7 | 0.9300 |
Eu1—O1 | 2.324 (5) | C8—C9 | 1.352 (15) |
Eu1—O3 | 2.376 (5) | C8—H8 | 0.9300 |
Eu1—O3i | 2.376 (5) | C9—C10 | 1.375 (17) |
Eu1—O3ii | 2.376 (5) | C9—C12 | 1.519 (14) |
Eu1—O9i | 2.585 (6) | C10—C11 | 1.374 (16) |
Eu1—O9ii | 2.585 (6) | C10—H10 | 0.9300 |
Eu1—O9 | 2.585 (6) | C11—H11 | 0.9300 |
O1—C1 | 1.227 (9) | C12—H12A | 0.9600 |
O2—C1 | 1.243 (9) | C12—H12B | 0.9600 |
O3—C4iii | 1.209 (8) | C12—H12C | 0.9600 |
O4—C4 | 1.256 (9) | C13—C14 | 1.451 (15) |
O4—H4 | 0.821 (15) | C14—C15 | 1.360 (14) |
O5—C5 | 1.383 (12) | C14—C19 | 1.369 (15) |
O5—C2 | 1.406 (11) | C15—C16 | 1.383 (14) |
O6—C5 | 1.189 (11) | C15—H15 | 0.9300 |
O7—C13 | 1.341 (11) | C16—C17 | 1.353 (18) |
O7—C3 | 1.424 (8) | C16—H16 | 0.9300 |
O8—C13 | 1.212 (12) | C17—C18 | 1.37 (2) |
O9—C21 | 1.423 (11) | C17—C20 | 1.509 (18) |
O9—H9A | 0.860 (15) | C18—C19 | 1.33 (2) |
C1—C2 | 1.523 (10) | C18—H18 | 0.9300 |
C2—C3 | 1.499 (11) | C19—H19 | 0.9300 |
C2—H2 | 0.9800 | C20—H20A | 0.9600 |
C3—C4 | 1.513 (9) | C20—H20B | 0.9600 |
C3—H3 | 0.9800 | C20—H20C | 0.9600 |
C5—C6 | 1.426 (14) | C21—H21A | 0.9600 |
C6—C11 | 1.361 (16) | C21—H21B | 0.9600 |
C6—C7 | 1.371 (14) | C21—H21C | 0.9600 |
O1i—Eu1—O1ii | 80.4 (2) | O4—C4—C3 | 116.9 (7) |
O1i—Eu1—O1 | 80.4 (2) | O6—C5—O5 | 121.0 (10) |
O1ii—Eu1—O1 | 80.4 (2) | O6—C5—C6 | 127.1 (10) |
O1i—Eu1—O3 | 133.38 (19) | O5—C5—C6 | 111.9 (9) |
O1ii—Eu1—O3 | 140.35 (18) | C11—C6—C7 | 118.5 (10) |
O1—Eu1—O3 | 85.48 (18) | C11—C6—C5 | 122.7 (11) |
O1i—Eu1—O3i | 85.48 (18) | C7—C6—C5 | 118.7 (10) |
O1ii—Eu1—O3i | 133.38 (19) | C8—C7—C6 | 121.3 (10) |
O1—Eu1—O3i | 140.35 (18) | C8—C7—H7 | 119.4 |
O3—Eu1—O3i | 77.78 (19) | C6—C7—H7 | 119.4 |
O1i—Eu1—O3ii | 140.34 (18) | C7—C8—C9 | 121.1 (11) |
O1ii—Eu1—O3ii | 85.48 (18) | C7—C8—H8 | 119.4 |
O1—Eu1—O3ii | 133.38 (19) | C9—C8—H8 | 119.4 |
O3—Eu1—O3ii | 77.78 (19) | C8—C9—C10 | 118.0 (10) |
O3i—Eu1—O3ii | 77.78 (19) | C8—C9—C12 | 120.3 (11) |
O1i—Eu1—O9i | 69.9 (2) | C10—C9—C12 | 121.7 (11) |
O1ii—Eu1—O9i | 69.92 (19) | C11—C10—C9 | 121.3 (12) |
O1—Eu1—O9i | 140.64 (19) | C11—C10—H10 | 119.4 |
O3—Eu1—O9i | 133.77 (18) | C9—C10—H10 | 119.4 |
O3i—Eu1—O9i | 63.50 (18) | C6—C11—C10 | 119.7 (12) |
O3ii—Eu1—O9i | 70.46 (19) | C6—C11—H11 | 120.1 |
O1i—Eu1—O9ii | 140.64 (19) | C10—C11—H11 | 120.1 |
O1ii—Eu1—O9ii | 69.9 (2) | C9—C12—H12A | 109.5 |
O1—Eu1—O9ii | 69.92 (19) | C9—C12—H12B | 109.5 |
O3—Eu1—O9ii | 70.46 (19) | H12A—C12—H12B | 109.5 |
O3i—Eu1—O9ii | 133.78 (18) | C9—C12—H12C | 109.5 |
O3ii—Eu1—O9ii | 63.50 (18) | H12A—C12—H12C | 109.5 |
O9i—Eu1—O9ii | 119.82 (2) | H12B—C12—H12C | 109.5 |
O1i—Eu1—O9 | 69.92 (19) | O8—C13—O7 | 120.6 (10) |
O1ii—Eu1—O9 | 140.64 (19) | O8—C13—C14 | 127.4 (10) |
O1—Eu1—O9 | 69.9 (2) | O7—C13—C14 | 111.9 (9) |
O3—Eu1—O9 | 63.50 (18) | C15—C14—C19 | 117.7 (11) |
O3i—Eu1—O9 | 70.46 (19) | C15—C14—C13 | 121.7 (9) |
O3ii—Eu1—O9 | 133.78 (18) | C19—C14—C13 | 120.6 (11) |
O9i—Eu1—O9 | 119.82 (2) | C14—C15—C16 | 120.0 (10) |
O9ii—Eu1—O9 | 119.82 (2) | C14—C15—H15 | 120.0 |
C1—O1—Eu1 | 150.3 (5) | C16—C15—H15 | 120.0 |
C4iii—O3—Eu1 | 141.0 (5) | C17—C16—C15 | 121.8 (12) |
C4—O4—H4 | 123 (8) | C17—C16—H16 | 119.1 |
C5—O5—C2 | 115.5 (7) | C15—C16—H16 | 119.1 |
C13—O7—C3 | 117.1 (7) | C16—C17—C18 | 116.6 (14) |
C21—O9—Eu1 | 138.0 (6) | C16—C17—C20 | 120.7 (15) |
C21—O9—H9A | 97 (8) | C18—C17—C20 | 122.8 (16) |
Eu1—O9—H9A | 125 (9) | C19—C18—C17 | 122.3 (16) |
O1—C1—O2 | 127.6 (7) | C19—C18—H18 | 118.9 |
O1—C1—C2 | 113.6 (7) | C17—C18—H18 | 118.9 |
O2—C1—C2 | 118.8 (8) | C18—C19—C14 | 121.6 (15) |
O5—C2—C3 | 106.8 (6) | C18—C19—H19 | 119.2 |
O5—C2—C1 | 112.9 (7) | C14—C19—H19 | 119.2 |
C3—C2—C1 | 110.1 (7) | C17—C20—H20A | 109.5 |
O5—C2—H2 | 109.0 | C17—C20—H20B | 109.5 |
C3—C2—H2 | 109.0 | H20A—C20—H20B | 109.5 |
C1—C2—H2 | 109.0 | C17—C20—H20C | 109.5 |
O7—C3—C2 | 106.1 (6) | H20A—C20—H20C | 109.5 |
O7—C3—C4 | 113.8 (6) | H20B—C20—H20C | 109.5 |
C2—C3—C4 | 111.2 (6) | O9—C21—H21A | 109.5 |
O7—C3—H3 | 108.5 | O9—C21—H21B | 109.5 |
C2—C3—H3 | 108.5 | H21A—C21—H21B | 109.5 |
C4—C3—H3 | 108.5 | O9—C21—H21C | 109.5 |
O3iv—C4—O4 | 126.8 (6) | H21A—C21—H21C | 109.5 |
O3iv—C4—C3 | 116.4 (6) | H21B—C21—H21C | 109.5 |
Eu1—O1—C1—O2 | 14.8 (16) | C5—C6—C7—C8 | −175.4 (10) |
Eu1—O1—C1—C2 | −166.6 (8) | C6—C7—C8—C9 | −2.9 (19) |
C5—O5—C2—C3 | 165.8 (6) | C7—C8—C9—C10 | 2.4 (19) |
C5—O5—C2—C1 | −73.1 (10) | C7—C8—C9—C12 | −178.2 (12) |
O1—C1—C2—O5 | 177.7 (7) | C8—C9—C10—C11 | −2 (2) |
O2—C1—C2—O5 | −3.5 (11) | C12—C9—C10—C11 | 178.4 (13) |
O1—C1—C2—C3 | −63.1 (9) | C7—C6—C11—C10 | −2.8 (18) |
O2—C1—C2—C3 | 115.7 (8) | C5—C6—C11—C10 | 175.6 (11) |
C13—O7—C3—C2 | 164.8 (7) | C9—C10—C11—C6 | 2 (2) |
C13—O7—C3—C4 | −72.5 (9) | C3—O7—C13—O8 | 4.4 (13) |
O5—C2—C3—O7 | 54.1 (8) | C3—O7—C13—C14 | −173.6 (7) |
C1—C2—C3—O7 | −68.8 (8) | O8—C13—C14—C15 | 172.7 (11) |
O5—C2—C3—C4 | −70.2 (9) | O7—C13—C14—C15 | −9.6 (14) |
C1—C2—C3—C4 | 167.0 (7) | O8—C13—C14—C19 | −8.3 (18) |
O7—C3—C4—O3iv | 154.3 (6) | O7—C13—C14—C19 | 169.4 (10) |
C2—C3—C4—O3iv | −86.0 (9) | C19—C14—C15—C16 | −1.2 (16) |
O7—C3—C4—O4 | −26.4 (10) | C13—C14—C15—C16 | 177.9 (10) |
C2—C3—C4—O4 | 93.4 (9) | C14—C15—C16—C17 | −1.2 (18) |
C2—O5—C5—O6 | −3.9 (12) | C15—C16—C17—C18 | 2 (2) |
C2—O5—C5—C6 | 177.6 (7) | C15—C16—C17—C20 | −178.5 (14) |
O6—C5—C6—C11 | −168.8 (11) | C16—C17—C18—C19 | 0 (3) |
O5—C5—C6—C11 | 9.6 (13) | C20—C17—C18—C19 | −179.7 (17) |
O6—C5—C6—C7 | 9.7 (15) | C17—C18—C19—C14 | −2 (3) |
O5—C5—C6—C7 | −172.0 (9) | C15—C14—C19—C18 | 3 (2) |
C11—C6—C7—C8 | 3.1 (17) | C13—C14—C19—C18 | −176.2 (16) |
Symmetry codes: (i) −x+y+1, −x+1, z; (ii) −y+1, x−y, z; (iii) x, y, z−1; (iv) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9A···O8v | 0.86 (2) | 2.14 (6) | 2.930 (10) | 153 (12) |
O4—H4···O2iv | 0.82 (2) | 1.68 (3) | 2.480 (7) | 165 (12) |
C8—H8···Cgvi | 0.93 | 2.56 | 3.444 (6) | 160 |
Symmetry codes: (iv) x, y, z+1; (v) −x+y+1, −x+1, z−1; (vi) −x+y+5/3, −x+4/3, z−2/3. |