Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620009547/uk3197sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009547/uk3197CP1-Cesup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009547/uk3197CP2-Prsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009547/uk3197CP3-Ndsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009547/uk3197CP4-Smsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009547/uk3197CP5-Eusup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009547/uk3197CP6-Gdsup7.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620009547/uk3197sup8.pdf |
CCDC references: 2016037; 1915281; 1915280; 1915279; 1915278; 1915277
For all structures, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).
[Ce(C21H11O8)(C3H7NO)2] | Z = 2 |
Mr = 677.61 | F(000) = 678 |
Triclinic, P1 | Dx = 1.604 Mg m−3 |
a = 10.9515 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.2204 (11) Å | Cell parameters from 4246 reflections |
c = 12.2870 (12) Å | θ = 2.9–24.3° |
α = 103.223 (4)° | µ = 1.68 mm−1 |
β = 100.928 (4)° | T = 298 K |
γ = 100.379 (4)° | Block, colourless |
V = 1403.1 (2) Å3 | 0.30 × 0.20 × 0.20 mm |
Bruker APEXII CCD diffractometer | 4104 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.051 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.4°, θmin = 2.9° |
Tmin = 0.668, Tmax = 0.745 | h = −13→12 |
12741 measured reflections | k = −13→13 |
5012 independent reflections | l = −14→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0337P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.070 | (Δ/σ)max = 0.001 |
S = 1.00 | Δρmax = 0.65 e Å−3 |
5012 reflections | Δρmin = −0.56 e Å−3 |
366 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0010 (4) |
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 data for CP1–CP6 were collected on a Bruker SMART APEXII diffractometer equipped with 1 K CCD instrument, using a graphite monochromator with Mo Kα radiation (λ = 0.71073 Å) at room temperature. Absorption corrections were performed via the SADABS program (Bruker, 2001). All the structures were solved by means of direct methods with SHELXS-97 program (Sheldrick, 2008) and refined on F2 with full-matrix least-squares techniques using the program SHELXL-2014 program (Sheldrick, 2015). After all non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
Ce1 | −0.04421 (2) | −0.05548 (2) | 0.15048 (2) | 0.02386 (9) | |
C1 | 0.9055 (4) | 0.2011 (4) | 0.7261 (3) | 0.0353 (10) | |
C2 | 0.8313 (4) | 0.2871 (4) | 0.6836 (3) | 0.0316 (10) | |
C3 | 0.8770 (4) | 0.4170 (4) | 0.7259 (3) | 0.0367 (10) | |
H3 | 0.957486 | 0.450893 | 0.775870 | 0.044* | |
C4 | 0.8012 (4) | 0.4958 (4) | 0.6927 (3) | 0.0431 (11) | |
H4 | 0.830998 | 0.582544 | 0.722093 | 0.052* | |
C5 | 0.6832 (4) | 0.4478 (5) | 0.6173 (4) | 0.0449 (12) | |
H5 | 0.631516 | 0.500766 | 0.597817 | 0.054* | |
C6 | 0.6430 (4) | 0.3183 (5) | 0.5709 (3) | 0.0375 (11) | |
C7 | 0.7150 (4) | 0.2382 (4) | 0.6038 (3) | 0.0347 (10) | |
H7 | 0.685682 | 0.151647 | 0.572383 | 0.042* | |
C8 | 0.4934 (4) | 0.2887 (4) | 0.3903 (3) | 0.0307 (10) | |
C9 | 0.3712 (4) | 0.2306 (4) | 0.3234 (3) | 0.0289 (9) | |
H9 | 0.313489 | 0.181679 | 0.351441 | 0.035* | |
C10 | 0.3360 (3) | 0.2461 (4) | 0.2141 (3) | 0.0253 (9) | |
C11 | 0.4205 (4) | 0.3241 (4) | 0.1746 (3) | 0.0271 (9) | |
H11 | 0.396485 | 0.336458 | 0.102012 | 0.033* | |
C12 | 0.5403 (4) | 0.3828 (4) | 0.2447 (3) | 0.0269 (9) | |
C13 | 0.5793 (4) | 0.3645 (4) | 0.3516 (3) | 0.0304 (9) | |
H13 | 0.661604 | 0.402393 | 0.396772 | 0.036* | |
C14 | 0.2036 (4) | 0.1815 (4) | 0.1400 (3) | 0.0310 (9) | |
C15 | 0.6976 (3) | 0.4277 (4) | 0.1400 (3) | 0.0241 (9) | |
C16 | 0.7312 (3) | 0.3141 (4) | 0.1301 (3) | 0.0260 (9) | |
H16 | 0.700792 | 0.259999 | 0.171145 | 0.031* | |
C17 | 0.8107 (3) | 0.2805 (4) | 0.0589 (3) | 0.0279 (9) | |
C18 | 0.8565 (4) | 0.3624 (4) | −0.0016 (3) | 0.0352 (10) | |
H18 | 0.908887 | 0.340050 | −0.050364 | 0.042* | |
C19 | 0.8236 (4) | 0.4765 (4) | 0.0112 (4) | 0.0389 (11) | |
H19 | 0.855410 | 0.531687 | −0.028289 | 0.047* | |
C20 | 0.7442 (4) | 0.5108 (4) | 0.0817 (3) | 0.0308 (9) | |
H20 | 0.722487 | 0.588192 | 0.089883 | 0.037* | |
C21 | 0.8506 (4) | 0.1585 (4) | 0.0518 (4) | 0.0326 (10) | |
O10 | −0.0450 (3) | 0.0601 (3) | 0.3513 (3) | 0.0558 (9) | |
C25 | 0.0402 (6) | 0.1244 (6) | 0.4335 (5) | 0.0682 (16) | |
H25 | 0.098032 | 0.082858 | 0.465107 | 0.082* | |
N2 | 0.0601 (5) | 0.2425 (5) | 0.4820 (4) | 0.0703 (14) | |
C26 | 0.1619 (8) | 0.3139 (8) | 0.5772 (6) | 0.144 (4) | |
H26A | 0.127841 | 0.350854 | 0.639727 | 0.216* | |
H26B | 0.212888 | 0.379251 | 0.555241 | 0.216* | |
H26C | 0.214126 | 0.259878 | 0.600958 | 0.216* | |
C27 | −0.0309 (9) | 0.3117 (8) | 0.4325 (7) | 0.134 (3) | |
H27A | 0.010854 | 0.365127 | 0.393056 | 0.202* | |
H27B | −0.058280 | 0.362080 | 0.493376 | 0.202* | |
H27C | −0.103917 | 0.252319 | 0.379158 | 0.202* | |
O9 | −0.2580 (3) | −0.1427 (3) | 0.1877 (3) | 0.0466 (8) | |
C22 | −0.3440 (5) | −0.0892 (6) | 0.1951 (6) | 0.0761 (19) | |
H22 | −0.322886 | −0.004806 | 0.196048 | 0.091* | |
C24 | −0.5549 (6) | −0.0578 (7) | 0.2051 (9) | 0.138 (3) | |
H24A | −0.539338 | −0.001601 | 0.280615 | 0.206* | |
H24B | −0.636883 | −0.115241 | 0.187299 | 0.206* | |
H24C | −0.554039 | −0.010033 | 0.149476 | 0.206* | |
C23 | −0.5022 (6) | −0.2675 (6) | 0.1821 (7) | 0.102 (2) | |
H23A | −0.513927 | −0.309286 | 0.102118 | 0.154* | |
H23B | −0.582023 | −0.284815 | 0.203648 | 0.154* | |
H23C | −0.439801 | −0.297434 | 0.227930 | 0.154* | |
N1 | −0.4567 (4) | −0.1275 (5) | 0.2018 (4) | 0.0664 (13) | |
O1 | 0.8522 (3) | 0.0867 (3) | 0.7059 (3) | 0.0495 (8) | |
O2 | 1.0185 (3) | 0.2475 (3) | 0.7872 (2) | 0.0404 (7) | |
O3 | 0.5219 (3) | 0.2623 (3) | 0.4966 (2) | 0.0512 (9) | |
O4 | 0.1223 (3) | 0.1356 (3) | 0.1874 (2) | 0.0362 (7) | |
O5 | 0.1857 (3) | 0.1789 (3) | 0.0355 (2) | 0.0457 (8) | |
O6 | 0.6216 (2) | 0.4708 (2) | 0.2113 (2) | 0.0320 (7) | |
O7 | 0.8252 (3) | 0.0997 (3) | 0.1233 (3) | 0.0455 (8) | |
O8 | 0.9069 (3) | 0.1192 (3) | −0.0247 (3) | 0.0469 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ce1 | 0.01807 (13) | 0.02176 (14) | 0.02923 (14) | 0.00634 (9) | 0.00019 (9) | 0.00523 (10) |
C1 | 0.031 (3) | 0.041 (3) | 0.036 (2) | 0.015 (2) | 0.003 (2) | 0.014 (2) |
C2 | 0.031 (2) | 0.037 (3) | 0.027 (2) | 0.012 (2) | 0.0015 (18) | 0.011 (2) |
C3 | 0.037 (3) | 0.042 (3) | 0.027 (2) | 0.014 (2) | −0.0008 (19) | 0.005 (2) |
C4 | 0.057 (3) | 0.036 (3) | 0.034 (2) | 0.020 (2) | 0.002 (2) | 0.005 (2) |
C5 | 0.049 (3) | 0.051 (3) | 0.042 (3) | 0.027 (3) | 0.003 (2) | 0.021 (3) |
C6 | 0.025 (2) | 0.055 (3) | 0.034 (2) | 0.011 (2) | −0.0021 (19) | 0.022 (2) |
C7 | 0.035 (3) | 0.035 (3) | 0.032 (2) | 0.009 (2) | 0.002 (2) | 0.010 (2) |
C8 | 0.025 (2) | 0.035 (3) | 0.033 (2) | 0.011 (2) | 0.0002 (18) | 0.015 (2) |
C9 | 0.023 (2) | 0.030 (2) | 0.037 (2) | 0.0080 (19) | 0.0088 (18) | 0.013 (2) |
C10 | 0.022 (2) | 0.022 (2) | 0.028 (2) | 0.0069 (17) | 0.0029 (17) | 0.0008 (18) |
C11 | 0.032 (2) | 0.030 (2) | 0.024 (2) | 0.013 (2) | 0.0073 (18) | 0.0095 (19) |
C12 | 0.027 (2) | 0.022 (2) | 0.037 (2) | 0.0098 (18) | 0.0161 (19) | 0.0074 (19) |
C13 | 0.014 (2) | 0.037 (3) | 0.039 (2) | 0.0079 (19) | 0.0017 (17) | 0.010 (2) |
C14 | 0.032 (2) | 0.021 (2) | 0.038 (2) | 0.0090 (19) | 0.005 (2) | 0.004 (2) |
C15 | 0.020 (2) | 0.025 (2) | 0.027 (2) | 0.0071 (17) | 0.0061 (17) | 0.0037 (18) |
C16 | 0.023 (2) | 0.028 (2) | 0.029 (2) | 0.0084 (18) | 0.0079 (17) | 0.0094 (19) |
C17 | 0.020 (2) | 0.029 (2) | 0.031 (2) | 0.0062 (18) | 0.0004 (17) | 0.0061 (19) |
C18 | 0.029 (2) | 0.040 (3) | 0.037 (2) | 0.007 (2) | 0.0136 (19) | 0.006 (2) |
C19 | 0.042 (3) | 0.037 (3) | 0.043 (3) | 0.006 (2) | 0.019 (2) | 0.017 (2) |
C20 | 0.035 (2) | 0.021 (2) | 0.037 (2) | 0.0053 (19) | 0.009 (2) | 0.0086 (19) |
C21 | 0.018 (2) | 0.033 (3) | 0.041 (2) | 0.0103 (19) | 0.0002 (19) | 0.002 (2) |
O10 | 0.051 (2) | 0.062 (2) | 0.0378 (18) | 0.0028 (18) | 0.0064 (16) | −0.0069 (17) |
C25 | 0.068 (4) | 0.071 (5) | 0.055 (3) | −0.001 (3) | 0.019 (3) | 0.007 (3) |
N2 | 0.101 (4) | 0.044 (3) | 0.050 (3) | −0.017 (3) | 0.033 (3) | −0.006 (2) |
C26 | 0.136 (8) | 0.148 (8) | 0.068 (4) | −0.087 (6) | 0.024 (5) | −0.032 (5) |
C27 | 0.204 (10) | 0.079 (6) | 0.136 (7) | 0.027 (6) | 0.071 (7) | 0.039 (6) |
O9 | 0.0253 (17) | 0.049 (2) | 0.071 (2) | 0.0104 (16) | 0.0181 (16) | 0.0203 (18) |
C22 | 0.047 (3) | 0.062 (4) | 0.138 (6) | 0.013 (3) | 0.041 (4) | 0.049 (4) |
C24 | 0.069 (5) | 0.089 (6) | 0.278 (11) | 0.045 (4) | 0.082 (6) | 0.041 (7) |
C23 | 0.073 (5) | 0.069 (5) | 0.168 (7) | 0.008 (4) | 0.048 (5) | 0.028 (5) |
N1 | 0.041 (3) | 0.079 (4) | 0.092 (3) | 0.029 (3) | 0.030 (2) | 0.024 (3) |
O1 | 0.0433 (19) | 0.0313 (19) | 0.062 (2) | 0.0063 (16) | −0.0157 (16) | 0.0146 (17) |
O2 | 0.0295 (17) | 0.0363 (19) | 0.0542 (18) | 0.0101 (15) | −0.0033 (15) | 0.0191 (16) |
O3 | 0.0335 (18) | 0.074 (3) | 0.0483 (18) | 0.0039 (17) | −0.0057 (15) | 0.0398 (19) |
O4 | 0.0255 (16) | 0.0315 (17) | 0.0420 (16) | −0.0046 (13) | 0.0010 (14) | 0.0055 (14) |
O5 | 0.0379 (19) | 0.055 (2) | 0.0315 (16) | −0.0036 (16) | −0.0048 (14) | 0.0081 (15) |
O6 | 0.0328 (16) | 0.0237 (16) | 0.0446 (16) | 0.0078 (13) | 0.0221 (14) | 0.0078 (14) |
O7 | 0.0472 (19) | 0.041 (2) | 0.065 (2) | 0.0276 (16) | 0.0224 (17) | 0.0261 (18) |
O8 | 0.0344 (18) | 0.050 (2) | 0.0541 (19) | 0.0201 (16) | 0.0131 (15) | 0.0006 (17) |
Ce1—O8i | 2.434 (3) | C15—C16 | 1.375 (5) |
Ce1—O4 | 2.441 (3) | C15—C20 | 1.384 (5) |
Ce1—O5ii | 2.445 (3) | C15—O6 | 1.386 (4) |
Ce1—O7iii | 2.485 (3) | C16—C17 | 1.386 (5) |
Ce1—O2iv | 2.490 (3) | C16—H16 | 0.9300 |
Ce1—O10 | 2.513 (3) | C17—C18 | 1.392 (5) |
Ce1—O9 | 2.536 (3) | C17—C21 | 1.499 (5) |
Ce1—O1iv | 2.608 (3) | C18—C19 | 1.375 (6) |
Ce1—C1iv | 2.904 (4) | C18—H18 | 0.9300 |
C1—O1 | 1.257 (5) | C19—C20 | 1.381 (5) |
C1—O2 | 1.266 (5) | C19—H19 | 0.9300 |
C1—C2 | 1.488 (5) | C20—H20 | 0.9300 |
C2—C7 | 1.384 (5) | C21—O7 | 1.255 (5) |
C2—C3 | 1.392 (6) | C21—O8 | 1.259 (5) |
C3—C4 | 1.393 (6) | O10—C25 | 1.216 (6) |
C3—H3 | 0.9300 | C25—N2 | 1.282 (7) |
C4—C5 | 1.373 (6) | C25—H25 | 0.9300 |
C4—H4 | 0.9300 | N2—C26 | 1.417 (8) |
C5—C6 | 1.388 (6) | N2—C27 | 1.494 (9) |
C5—H5 | 0.9300 | C26—H26A | 0.9600 |
C6—C7 | 1.375 (6) | C26—H26B | 0.9600 |
C6—O3 | 1.403 (5) | C26—H26C | 0.9600 |
C7—H7 | 0.9300 | C27—H27A | 0.9600 |
C8—C13 | 1.379 (5) | C27—H27B | 0.9600 |
C8—C9 | 1.383 (5) | C27—H27C | 0.9600 |
C8—O3 | 1.395 (4) | O9—C22 | 1.212 (6) |
C9—C10 | 1.384 (5) | C22—N1 | 1.256 (6) |
C9—H9 | 0.9300 | C22—H22 | 0.9300 |
C10—C11 | 1.389 (5) | C24—N1 | 1.441 (7) |
C10—C14 | 1.509 (5) | C24—H24A | 0.9600 |
C11—C12 | 1.378 (5) | C24—H24B | 0.9600 |
C11—H11 | 0.9300 | C24—H24C | 0.9600 |
C12—C13 | 1.376 (5) | C23—N1 | 1.507 (7) |
C12—O6 | 1.393 (4) | C23—H23A | 0.9600 |
C13—H13 | 0.9300 | C23—H23B | 0.9600 |
C14—O4 | 1.251 (4) | C23—H23C | 0.9600 |
C14—O5 | 1.254 (4) | ||
O8i—Ce1—O4 | 76.36 (10) | C11—C12—O6 | 119.7 (3) |
O8i—Ce1—O5ii | 73.39 (10) | C12—C13—C8 | 118.4 (4) |
O4—Ce1—O5ii | 126.98 (9) | C12—C13—H13 | 120.8 |
O8i—Ce1—O7iii | 123.04 (10) | C8—C13—H13 | 120.8 |
O4—Ce1—O7iii | 78.82 (10) | O4—C14—O5 | 126.1 (4) |
O5ii—Ce1—O7iii | 82.58 (11) | O4—C14—C10 | 117.7 (3) |
O8i—Ce1—O2iv | 84.07 (10) | O5—C14—C10 | 116.2 (4) |
O4—Ce1—O2iv | 126.32 (9) | C16—C15—C20 | 120.9 (3) |
O5ii—Ce1—O2iv | 92.55 (10) | C16—C15—O6 | 124.0 (3) |
O7iii—Ce1—O2iv | 148.94 (9) | C20—C15—O6 | 115.0 (3) |
O8i—Ce1—O10 | 144.00 (11) | C15—C16—C17 | 119.9 (3) |
O4—Ce1—O10 | 78.11 (10) | C15—C16—H16 | 120.1 |
O5ii—Ce1—O10 | 142.58 (11) | C17—C16—H16 | 120.1 |
O7iii—Ce1—O10 | 75.46 (11) | C16—C17—C18 | 119.7 (4) |
O2iv—Ce1—O10 | 91.08 (11) | C16—C17—C21 | 119.5 (3) |
O8i—Ce1—O9 | 138.89 (11) | C18—C17—C21 | 120.8 (4) |
O4—Ce1—O9 | 144.08 (10) | C19—C18—C17 | 119.5 (4) |
O5ii—Ce1—O9 | 72.79 (10) | C19—C18—H18 | 120.3 |
O7iii—Ce1—O9 | 74.43 (10) | C17—C18—H18 | 120.3 |
O2iv—Ce1—O9 | 74.82 (9) | C18—C19—C20 | 121.3 (4) |
O10—Ce1—O9 | 72.32 (11) | C18—C19—H19 | 119.4 |
O8i—Ce1—O1iv | 77.93 (10) | C20—C19—H19 | 119.4 |
O4—Ce1—O1iv | 75.75 (9) | C19—C20—C15 | 118.7 (4) |
O5ii—Ce1—O1iv | 135.85 (11) | C19—C20—H20 | 120.6 |
O7iii—Ce1—O1iv | 141.56 (11) | C15—C20—H20 | 120.6 |
O2iv—Ce1—O1iv | 51.25 (9) | O7—C21—O8 | 123.0 (4) |
O10—Ce1—O1iv | 71.45 (11) | O7—C21—C17 | 117.6 (4) |
O9—Ce1—O1iv | 112.36 (10) | O8—C21—C17 | 119.4 (4) |
O8i—Ce1—C1iv | 78.35 (11) | C25—O10—Ce1 | 132.4 (3) |
O4—Ce1—C1iv | 100.77 (11) | O10—C25—N2 | 127.9 (7) |
O5ii—Ce1—C1iv | 114.14 (12) | O10—C25—H25 | 116.0 |
O7iii—Ce1—C1iv | 157.06 (11) | N2—C25—H25 | 116.0 |
O2iv—Ce1—C1iv | 25.70 (11) | C25—N2—C26 | 125.9 (7) |
O10—Ce1—C1iv | 81.98 (12) | C25—N2—C27 | 117.1 (6) |
O9—Ce1—C1iv | 94.91 (11) | C26—N2—C27 | 117.0 (6) |
O1iv—Ce1—C1iv | 25.65 (11) | N2—C26—H26A | 109.5 |
O1—C1—O2 | 122.1 (4) | N2—C26—H26B | 109.5 |
O1—C1—C2 | 119.3 (4) | H26A—C26—H26B | 109.5 |
O2—C1—C2 | 118.5 (4) | N2—C26—H26C | 109.5 |
O1—C1—Ce1iv | 63.9 (2) | H26A—C26—H26C | 109.5 |
O2—C1—Ce1iv | 58.5 (2) | H26B—C26—H26C | 109.5 |
C2—C1—Ce1iv | 169.6 (3) | N2—C27—H27A | 109.5 |
C7—C2—C3 | 119.6 (4) | N2—C27—H27B | 109.5 |
C7—C2—C1 | 120.1 (4) | H27A—C27—H27B | 109.5 |
C3—C2—C1 | 120.3 (4) | N2—C27—H27C | 109.5 |
C2—C3—C4 | 119.4 (4) | H27A—C27—H27C | 109.5 |
C2—C3—H3 | 120.3 | H27B—C27—H27C | 109.5 |
C4—C3—H3 | 120.3 | C22—O9—Ce1 | 126.4 (3) |
C5—C4—C3 | 121.3 (4) | O9—C22—N1 | 131.4 (6) |
C5—C4—H4 | 119.4 | O9—C22—H22 | 114.3 |
C3—C4—H4 | 119.4 | N1—C22—H22 | 114.3 |
C4—C5—C6 | 118.2 (4) | N1—C24—H24A | 109.5 |
C4—C5—H5 | 120.9 | N1—C24—H24B | 109.5 |
C6—C5—H5 | 120.9 | H24A—C24—H24B | 109.5 |
C7—C6—C5 | 121.6 (4) | N1—C24—H24C | 109.5 |
C7—C6—O3 | 116.7 (4) | H24A—C24—H24C | 109.5 |
C5—C6—O3 | 121.4 (4) | H24B—C24—H24C | 109.5 |
C6—C7—C2 | 119.7 (4) | N1—C23—H23A | 109.5 |
C6—C7—H7 | 120.1 | N1—C23—H23B | 109.5 |
C2—C7—H7 | 120.1 | H23A—C23—H23B | 109.5 |
C13—C8—C9 | 121.3 (3) | N1—C23—H23C | 109.5 |
C13—C8—O3 | 123.7 (4) | H23A—C23—H23C | 109.5 |
C9—C8—O3 | 115.0 (3) | H23B—C23—H23C | 109.5 |
C8—C9—C10 | 119.3 (3) | C22—N1—C24 | 127.4 (6) |
C8—C9—H9 | 120.4 | C22—N1—C23 | 116.4 (5) |
C10—C9—H9 | 120.4 | C24—N1—C23 | 115.2 (5) |
C9—C10—C11 | 120.2 (4) | C1—O1—Ce1iv | 90.4 (2) |
C9—C10—C14 | 119.6 (3) | C1—O2—Ce1iv | 95.8 (2) |
C11—C10—C14 | 120.3 (3) | C8—O3—C6 | 119.0 (3) |
C12—C11—C10 | 119.0 (3) | C14—O4—Ce1 | 139.1 (3) |
C12—C11—H11 | 120.5 | C14—O5—Ce1ii | 139.6 (3) |
C10—C11—H11 | 120.5 | C15—O6—C12 | 118.3 (3) |
C13—C12—C11 | 121.8 (3) | C21—O7—Ce1v | 114.8 (2) |
C13—C12—O6 | 118.3 (4) | C21—O8—Ce1i | 171.7 (3) |
O1—C1—C2—C7 | −13.1 (6) | C15—C16—C17—C21 | 177.9 (3) |
O2—C1—C2—C7 | 170.9 (4) | C16—C17—C18—C19 | 0.8 (6) |
Ce1iv—C1—C2—C7 | −118.2 (17) | C21—C17—C18—C19 | −176.6 (4) |
O1—C1—C2—C3 | 165.5 (4) | C17—C18—C19—C20 | −1.0 (6) |
O2—C1—C2—C3 | −10.5 (6) | C18—C19—C20—C15 | 0.0 (6) |
Ce1iv—C1—C2—C3 | 60.3 (18) | C16—C15—C20—C19 | 1.3 (6) |
C7—C2—C3—C4 | 4.1 (6) | O6—C15—C20—C19 | 178.3 (3) |
C1—C2—C3—C4 | −174.5 (4) | C16—C17—C21—O7 | −9.9 (5) |
C2—C3—C4—C5 | −1.3 (6) | C18—C17—C21—O7 | 167.5 (4) |
C3—C4—C5—C6 | −2.6 (6) | C16—C17—C21—O8 | 169.7 (4) |
C4—C5—C6—C7 | 3.7 (6) | C18—C17—C21—O8 | −12.8 (6) |
C4—C5—C6—O3 | 177.7 (4) | Ce1—O10—C25—N2 | 114.4 (6) |
C5—C6—C7—C2 | −0.9 (6) | O10—C25—N2—C26 | −179.2 (5) |
O3—C6—C7—C2 | −175.2 (3) | O10—C25—N2—C27 | −0.4 (8) |
C3—C2—C7—C6 | −3.0 (6) | Ce1—O9—C22—N1 | 171.9 (5) |
C1—C2—C7—C6 | 175.6 (4) | O9—C22—N1—C24 | −176.9 (8) |
C13—C8—C9—C10 | 1.9 (6) | O9—C22—N1—C23 | −9.2 (11) |
O3—C8—C9—C10 | −176.9 (4) | O2—C1—O1—Ce1iv | 7.1 (4) |
C8—C9—C10—C11 | −3.1 (6) | C2—C1—O1—Ce1iv | −168.8 (3) |
C8—C9—C10—C14 | 179.1 (4) | O1—C1—O2—Ce1iv | −7.4 (4) |
C9—C10—C11—C12 | 1.6 (6) | C2—C1—O2—Ce1iv | 168.5 (3) |
C14—C10—C11—C12 | 179.4 (3) | C13—C8—O3—C6 | 2.0 (6) |
C10—C11—C12—C13 | 1.2 (6) | C9—C8—O3—C6 | −179.2 (4) |
C10—C11—C12—O6 | −173.7 (3) | C7—C6—O3—C8 | −121.8 (4) |
C11—C12—C13—C8 | −2.4 (6) | C5—C6—O3—C8 | 64.0 (5) |
O6—C12—C13—C8 | 172.6 (3) | O5—C14—O4—Ce1 | 43.1 (6) |
C9—C8—C13—C12 | 0.8 (6) | C10—C14—O4—Ce1 | −136.8 (3) |
O3—C8—C13—C12 | 179.5 (4) | O4—C14—O5—Ce1ii | −23.5 (7) |
C9—C10—C14—O4 | 13.3 (5) | C10—C14—O5—Ce1ii | 156.4 (3) |
C11—C10—C14—O4 | −164.6 (4) | C16—C15—O6—C12 | −22.6 (5) |
C9—C10—C14—O5 | −166.6 (4) | C20—C15—O6—C12 | 160.6 (3) |
C11—C10—C14—O5 | 15.5 (6) | C13—C12—O6—C15 | 99.0 (4) |
C20—C15—C16—C17 | −1.5 (6) | C11—C12—O6—C15 | −85.9 (4) |
O6—C15—C16—C17 | −178.2 (3) | O8—C21—O7—Ce1v | 20.5 (5) |
C15—C16—C17—C18 | 0.4 (6) | C17—C21—O7—Ce1v | −159.8 (3) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) x−1, y, z; (iv) −x+1, −y, −z+1; (v) x+1, y, z. |
[Pr(C21H11O8)(C3H7NO)2] | Z = 2 |
Mr = 678.40 | F(000) = 680 |
Triclinic, P1 | Dx = 1.609 Mg m−3 |
a = 10.9076 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1726 (13) Å | Cell parameters from 7409 reflections |
c = 12.3717 (16) Å | θ = 2.9–24.4° |
α = 102.985 (3)° | µ = 1.80 mm−1 |
β = 101.259 (3)° | T = 298 K |
γ = 100.483 (3)° | Block, green |
V = 1400.1 (3) Å3 | 0.30 × 0.20 × 0.15 mm |
Bruker APEXII CCD diffractometer | 3777 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.095 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.5°, θmin = 2.4° |
Tmin = 0.636, Tmax = 0.746 | h = −13→13 |
26551 measured reflections | k = −13→13 |
5194 independent reflections | l = −14→14 |
Refinement on F2 | 24 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0345P)2 + 0.0377P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5194 reflections | Δρmax = 0.61 e Å−3 |
365 parameters | Δρmin = −0.56 e Å−3 |
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 data for CP1–CP6 were collected on a Bruker SMART APEXII diffractometer equipped with 1 K CCD instrument, using a graphite monochromator with Mo Kα radiation (λ = 0.71073 Å) at room temperature. Absorption corrections were performed via the SADABS program (Bruker, 2001). All the structures were solved by means of direct methods with SHELXS-97 program (Sheldrick, 2008) and refined on F2 with full-matrix least-squares techniques using the program SHELXL-2014 program (Sheldrick, 2015). After all non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
Pr1 | 0.45621 (3) | 0.44394 (3) | 1.14945 (3) | 0.02472 (11) | |
C1 | 0.2953 (5) | 0.3206 (4) | 0.8627 (5) | 0.0301 (13) | |
C2 | 0.1627 (4) | 0.2542 (4) | 0.7870 (4) | 0.0244 (12) | |
C3 | 0.0768 (5) | 0.1770 (4) | 0.8256 (4) | 0.0277 (13) | |
H3 | 0.099909 | 0.165841 | 0.898477 | 0.033* | |
C4 | −0.0430 (5) | 0.1170 (4) | 0.7552 (4) | 0.0250 (12) | |
C5 | −0.0800 (5) | 0.1354 (5) | 0.6488 (5) | 0.0309 (13) | |
H5 | −0.162491 | 0.096820 | 0.603217 | 0.037* | |
C6 | 0.0060 (5) | 0.2117 (5) | 0.6098 (4) | 0.0306 (13) | |
C7 | 0.1285 (5) | 0.2699 (4) | 0.6785 (5) | 0.0292 (13) | |
H7 | 0.187299 | 0.319427 | 0.651601 | 0.035* | |
C8 | −0.1428 (5) | 0.1811 (6) | 0.4291 (5) | 0.0385 (15) | |
C9 | −0.1839 (6) | 0.0513 (5) | 0.3831 (5) | 0.0435 (15) | |
H9 | −0.132455 | −0.001885 | 0.403556 | 0.052* | |
C10 | −0.3018 (6) | 0.0027 (5) | 0.3070 (5) | 0.0453 (16) | |
H10 | −0.331774 | −0.084319 | 0.277178 | 0.054* | |
C11 | −0.3767 (5) | 0.0825 (5) | 0.2742 (4) | 0.0364 (14) | |
H11 | −0.457363 | 0.048669 | 0.223708 | 0.044* | |
C12 | −0.3318 (5) | 0.2119 (5) | 0.3164 (4) | 0.0309 (13) | |
C13 | −0.4050 (5) | 0.2992 (5) | 0.2725 (4) | 0.0335 (14) | |
C14 | −0.2148 (5) | 0.2615 (5) | 0.3956 (5) | 0.0360 (14) | |
H14 | −0.184979 | 0.348466 | 0.426083 | 0.043* | |
C15 | −0.1991 (4) | 0.0710 (4) | 0.8600 (4) | 0.0230 (12) | |
C16 | −0.2329 (5) | 0.1849 (4) | 0.8704 (4) | 0.0271 (12) | |
H16 | −0.202832 | 0.239808 | 0.829864 | 0.032* | |
C17 | −0.3121 (5) | 0.2177 (5) | 0.9416 (4) | 0.0278 (13) | |
C18 | −0.3550 (5) | 0.1355 (5) | 1.0031 (5) | 0.0382 (14) | |
H18 | −0.406146 | 0.157900 | 1.052589 | 0.046* | |
C19 | −0.3214 (5) | 0.0209 (5) | 0.9904 (5) | 0.0393 (15) | |
H19 | −0.351422 | −0.034634 | 1.030500 | 0.047* | |
C20 | −0.2435 (5) | −0.0120 (5) | 0.9186 (4) | 0.0309 (13) | |
H20 | −0.221164 | −0.089466 | 0.909945 | 0.037* | |
C21 | −0.3524 (5) | 0.3416 (5) | 0.9508 (5) | 0.0348 (14) | |
C22 | 0.1574 (7) | 0.4115 (7) | 1.1947 (7) | 0.072 (2) | |
H22 | 0.179262 | 0.496769 | 1.197381 | 0.087* | |
C23 | −0.0010 (7) | 0.2338 (7) | 1.1828 (8) | 0.103 (3) | |
H23A | −0.007900 | 0.191044 | 1.104523 | 0.154* | |
H23B | −0.083636 | 0.215788 | 1.199560 | 0.154* | |
H23C | 0.059509 | 0.205224 | 1.232350 | 0.154* | |
C24 | −0.0526 (7) | 0.4431 (8) | 1.2056 (10) | 0.144 (4) | |
H24A | −0.042380 | 0.490512 | 1.283146 | 0.216* | |
H24B | −0.136089 | 0.386062 | 1.178275 | 0.216* | |
H24C | −0.044459 | 0.500121 | 1.158347 | 0.216* | |
C25 | 0.5404 (7) | 0.6220 (7) | 1.4279 (6) | 0.074 (2) | |
H25 | 0.599119 | 0.579055 | 1.456384 | 0.088* | |
C26 | 0.6630 (9) | 0.8088 (9) | 1.5760 (7) | 0.161 (5) | |
H26A | 0.628455 | 0.850131 | 1.635840 | 0.242* | |
H26B | 0.718034 | 0.871161 | 1.553588 | 0.242* | |
H26C | 0.711648 | 0.753432 | 1.603188 | 0.242* | |
C27 | 0.4699 (11) | 0.8100 (9) | 1.4343 (9) | 0.148 (4) | |
H27A | 0.434317 | 0.771215 | 1.353973 | 0.222* | |
H27B | 0.514937 | 0.895840 | 1.445891 | 0.222* | |
H27C | 0.401797 | 0.808736 | 1.473193 | 0.222* | |
N1 | 0.5616 (7) | 0.7382 (6) | 1.4813 (5) | 0.0776 (19) | |
N2 | 0.0440 (5) | 0.3730 (5) | 1.2011 (5) | 0.0651 (16) | |
O1 | 0.3132 (3) | 0.3230 (3) | 0.9661 (3) | 0.0432 (10) | |
O2 | 0.3773 (3) | 0.3666 (3) | 0.8157 (3) | 0.0363 (9) | |
O3 | −0.0208 (3) | 0.2363 (4) | 0.5040 (3) | 0.0499 (11) | |
O4 | −0.3518 (4) | 0.4135 (3) | 0.2923 (3) | 0.0502 (11) | |
O5 | −0.5188 (3) | 0.2525 (3) | 0.2118 (3) | 0.0408 (10) | |
O6 | −0.1252 (3) | 0.0288 (3) | 0.7871 (3) | 0.0325 (9) | |
O7 | −0.3286 (4) | 0.4005 (3) | 0.8793 (3) | 0.0454 (11) | |
O8 | −0.4082 (3) | 0.3787 (3) | 1.0275 (3) | 0.0479 (11) | |
O9 | 0.2428 (3) | 0.3580 (3) | 1.1857 (3) | 0.0453 (10) | |
O10 | 0.4556 (4) | 0.5593 (4) | 1.3460 (3) | 0.0571 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pr1 | 0.01852 (17) | 0.02435 (17) | 0.02988 (19) | 0.00752 (12) | 0.00117 (12) | 0.00667 (13) |
C1 | 0.031 (3) | 0.019 (3) | 0.036 (4) | 0.006 (3) | 0.003 (3) | 0.004 (3) |
C2 | 0.019 (3) | 0.023 (3) | 0.029 (3) | 0.007 (2) | 0.004 (3) | 0.002 (2) |
C3 | 0.033 (3) | 0.031 (3) | 0.020 (3) | 0.009 (3) | 0.006 (3) | 0.008 (3) |
C4 | 0.021 (3) | 0.025 (3) | 0.032 (3) | 0.011 (2) | 0.015 (3) | 0.004 (3) |
C5 | 0.018 (3) | 0.035 (3) | 0.036 (4) | 0.008 (3) | −0.001 (3) | 0.007 (3) |
C6 | 0.026 (3) | 0.037 (3) | 0.033 (4) | 0.013 (3) | 0.001 (3) | 0.021 (3) |
C7 | 0.016 (3) | 0.030 (3) | 0.045 (4) | 0.006 (2) | 0.009 (3) | 0.014 (3) |
C8 | 0.027 (3) | 0.065 (4) | 0.028 (3) | 0.014 (3) | 0.004 (3) | 0.022 (3) |
C9 | 0.052 (4) | 0.052 (4) | 0.037 (4) | 0.033 (3) | 0.009 (3) | 0.018 (3) |
C10 | 0.059 (4) | 0.043 (4) | 0.033 (4) | 0.023 (3) | 0.004 (3) | 0.007 (3) |
C11 | 0.035 (3) | 0.046 (4) | 0.028 (3) | 0.016 (3) | 0.003 (3) | 0.010 (3) |
C12 | 0.033 (3) | 0.034 (3) | 0.028 (3) | 0.014 (3) | 0.006 (3) | 0.011 (3) |
C13 | 0.036 (4) | 0.037 (4) | 0.027 (3) | 0.012 (3) | 0.002 (3) | 0.008 (3) |
C14 | 0.036 (4) | 0.040 (3) | 0.034 (4) | 0.014 (3) | 0.005 (3) | 0.014 (3) |
C15 | 0.014 (3) | 0.026 (3) | 0.027 (3) | 0.003 (2) | 0.003 (2) | 0.005 (3) |
C16 | 0.024 (3) | 0.030 (3) | 0.029 (3) | 0.004 (2) | 0.007 (3) | 0.012 (3) |
C17 | 0.021 (3) | 0.032 (3) | 0.030 (3) | 0.008 (2) | 0.003 (3) | 0.009 (3) |
C18 | 0.037 (4) | 0.041 (3) | 0.039 (4) | 0.009 (3) | 0.021 (3) | 0.006 (3) |
C19 | 0.046 (4) | 0.035 (3) | 0.044 (4) | 0.008 (3) | 0.020 (3) | 0.018 (3) |
C20 | 0.034 (3) | 0.025 (3) | 0.034 (3) | 0.011 (3) | 0.007 (3) | 0.008 (3) |
C21 | 0.015 (3) | 0.038 (3) | 0.045 (4) | 0.011 (3) | −0.001 (3) | 0.003 (3) |
C22 | 0.048 (5) | 0.062 (5) | 0.124 (7) | 0.011 (4) | 0.039 (5) | 0.045 (5) |
C23 | 0.078 (6) | 0.075 (6) | 0.161 (9) | 0.008 (5) | 0.046 (6) | 0.035 (6) |
C24 | 0.070 (6) | 0.094 (7) | 0.287 (14) | 0.045 (5) | 0.073 (8) | 0.043 (8) |
C25 | 0.076 (5) | 0.072 (5) | 0.058 (5) | −0.006 (4) | 0.023 (4) | 0.002 (4) |
C26 | 0.147 (9) | 0.181 (10) | 0.064 (6) | −0.098 (8) | 0.029 (5) | −0.041 (6) |
C27 | 0.217 (12) | 0.099 (7) | 0.169 (11) | 0.052 (7) | 0.100 (9) | 0.062 (7) |
N1 | 0.107 (5) | 0.059 (4) | 0.046 (4) | −0.026 (4) | 0.033 (3) | −0.003 (3) |
N2 | 0.039 (4) | 0.067 (4) | 0.099 (5) | 0.023 (3) | 0.030 (3) | 0.025 (3) |
O1 | 0.038 (2) | 0.050 (2) | 0.029 (2) | −0.0036 (19) | −0.0059 (19) | 0.007 (2) |
O2 | 0.026 (2) | 0.035 (2) | 0.039 (2) | −0.0026 (18) | 0.0023 (19) | 0.0039 (18) |
O3 | 0.032 (2) | 0.074 (3) | 0.046 (3) | 0.005 (2) | −0.003 (2) | 0.037 (2) |
O4 | 0.040 (2) | 0.034 (2) | 0.065 (3) | 0.008 (2) | −0.011 (2) | 0.011 (2) |
O5 | 0.028 (2) | 0.041 (2) | 0.052 (3) | 0.0082 (19) | −0.004 (2) | 0.019 (2) |
O6 | 0.033 (2) | 0.0246 (19) | 0.044 (2) | 0.0055 (17) | 0.0216 (19) | 0.0085 (18) |
O7 | 0.046 (3) | 0.042 (2) | 0.065 (3) | 0.026 (2) | 0.024 (2) | 0.029 (2) |
O8 | 0.035 (2) | 0.054 (3) | 0.054 (3) | 0.021 (2) | 0.016 (2) | 0.001 (2) |
O9 | 0.024 (2) | 0.047 (2) | 0.071 (3) | 0.0122 (19) | 0.020 (2) | 0.019 (2) |
O10 | 0.053 (3) | 0.061 (3) | 0.040 (3) | 0.003 (2) | 0.008 (2) | −0.008 (2) |
Pr1—O8i | 2.401 (4) | C15—C16 | 1.374 (6) |
Pr1—O2ii | 2.419 (4) | C15—C20 | 1.377 (6) |
Pr1—O1 | 2.425 (4) | C15—O6 | 1.384 (5) |
Pr1—O7iii | 2.460 (3) | C16—C17 | 1.387 (6) |
Pr1—O5iv | 2.473 (3) | C16—H16 | 0.9300 |
Pr1—O10 | 2.485 (4) | C17—C18 | 1.391 (7) |
Pr1—O9 | 2.516 (4) | C17—C21 | 1.514 (7) |
Pr1—O4iv | 2.589 (4) | C18—C19 | 1.379 (7) |
Pr1—C13iv | 2.885 (5) | C18—H18 | 0.9300 |
C1—O1 | 1.249 (6) | C19—C20 | 1.382 (7) |
C1—O2 | 1.255 (6) | C19—H19 | 0.9300 |
C1—C2 | 1.513 (7) | C20—H20 | 0.9300 |
C2—C7 | 1.381 (7) | C21—O7 | 1.254 (6) |
C2—C3 | 1.384 (6) | C21—O8 | 1.259 (6) |
C3—C4 | 1.375 (6) | C22—O9 | 1.205 (7) |
C3—H3 | 0.9300 | C22—N2 | 1.258 (7) |
C4—C5 | 1.372 (7) | C22—H22 | 0.9300 |
C4—O6 | 1.387 (6) | C23—N2 | 1.493 (8) |
C5—C6 | 1.382 (7) | C23—H23A | 0.9600 |
C5—H5 | 0.9300 | C23—H23B | 0.9600 |
C6—O3 | 1.384 (6) | C23—H23C | 0.9600 |
C6—C7 | 1.386 (6) | C24—N2 | 1.425 (8) |
C7—H7 | 0.9300 | C24—H24A | 0.9600 |
C8—C14 | 1.375 (7) | C24—H24B | 0.9600 |
C8—C9 | 1.386 (7) | C24—H24C | 0.9600 |
C8—O3 | 1.404 (6) | C25—O10 | 1.205 (7) |
C9—C10 | 1.370 (7) | C25—N1 | 1.273 (8) |
C9—H9 | 0.9300 | C25—H25 | 0.9300 |
C10—C11 | 1.387 (7) | C26—N1 | 1.407 (9) |
C10—H10 | 0.9300 | C26—H26A | 0.9600 |
C11—C12 | 1.381 (7) | C26—H26B | 0.9600 |
C11—H11 | 0.9300 | C26—H26C | 0.9600 |
C12—C14 | 1.381 (7) | C27—N1 | 1.502 (10) |
C12—C13 | 1.495 (7) | C27—H27A | 0.9600 |
C13—O4 | 1.250 (6) | C27—H27B | 0.9600 |
C13—O5 | 1.266 (6) | C27—H27C | 0.9600 |
C14—H14 | 0.9300 | ||
O8i—Pr1—O2ii | 76.43 (12) | O5—C13—C12 | 118.0 (5) |
O8i—Pr1—O1 | 73.82 (13) | O4—C13—Pr1v | 63.8 (3) |
O2ii—Pr1—O1 | 126.40 (12) | O5—C13—Pr1v | 58.5 (3) |
O8i—Pr1—O7iii | 123.04 (13) | C12—C13—Pr1v | 170.1 (4) |
O2ii—Pr1—O7iii | 78.34 (12) | C8—C14—C12 | 119.4 (5) |
O1—Pr1—O7iii | 81.97 (13) | C8—C14—H14 | 120.3 |
O8i—Pr1—O5iv | 83.53 (13) | C12—C14—H14 | 120.3 |
O2ii—Pr1—O5iv | 126.45 (12) | C16—C15—C20 | 121.0 (5) |
O1—Pr1—O5iv | 93.10 (12) | C16—C15—O6 | 123.3 (4) |
O7iii—Pr1—O5iv | 149.51 (13) | C20—C15—O6 | 115.6 (4) |
O8i—Pr1—O10 | 144.12 (14) | C15—C16—C17 | 119.7 (5) |
O2ii—Pr1—O10 | 78.49 (13) | C15—C16—H16 | 120.1 |
O1—Pr1—O10 | 142.03 (14) | C17—C16—H16 | 120.1 |
O7iii—Pr1—O10 | 75.52 (14) | C16—C17—C18 | 119.6 (5) |
O5iv—Pr1—O10 | 91.23 (13) | C16—C17—C21 | 119.8 (5) |
O8i—Pr1—O9 | 138.70 (13) | C18—C17—C21 | 120.6 (5) |
O2ii—Pr1—O9 | 144.20 (12) | C19—C18—C17 | 119.9 (5) |
O1—Pr1—O9 | 72.65 (13) | C19—C18—H18 | 120.0 |
O7iii—Pr1—O9 | 74.87 (12) | C17—C18—H18 | 120.0 |
O5iv—Pr1—O9 | 74.95 (12) | C18—C19—C20 | 120.4 (5) |
O10—Pr1—O9 | 72.17 (13) | C18—C19—H19 | 119.8 |
O8i—Pr1—O4iv | 77.65 (13) | C20—C19—H19 | 119.8 |
O2ii—Pr1—O4iv | 75.74 (12) | C15—C20—C19 | 119.4 (5) |
O1—Pr1—O4iv | 136.68 (12) | C15—C20—H20 | 120.3 |
O7iii—Pr1—O4iv | 141.33 (13) | C19—C20—H20 | 120.3 |
O5iv—Pr1—O4iv | 51.46 (11) | O7—C21—O8 | 124.0 (5) |
O10—Pr1—O4iv | 71.57 (13) | O7—C21—C17 | 117.0 (5) |
O9—Pr1—O4iv | 112.55 (13) | O8—C21—C17 | 119.0 (5) |
O8i—Pr1—C13iv | 77.79 (14) | O9—C22—N2 | 131.7 (7) |
O2ii—Pr1—C13iv | 100.73 (14) | O9—C22—H22 | 114.2 |
O1—Pr1—C13iv | 114.90 (14) | N2—C22—H22 | 114.2 |
O7iii—Pr1—C13iv | 157.43 (14) | N2—C23—H23A | 109.5 |
O5iv—Pr1—C13iv | 25.89 (12) | N2—C23—H23B | 109.5 |
O10—Pr1—C13iv | 82.17 (14) | H23A—C23—H23B | 109.5 |
O9—Pr1—C13iv | 95.20 (14) | N2—C23—H23C | 109.5 |
O4iv—Pr1—C13iv | 25.68 (12) | H23A—C23—H23C | 109.5 |
O1—C1—O2 | 126.2 (5) | H23B—C23—H23C | 109.5 |
O1—C1—C2 | 116.8 (5) | N2—C24—H24A | 109.5 |
O2—C1—C2 | 117.0 (5) | N2—C24—H24B | 109.5 |
C7—C2—C3 | 120.2 (5) | H24A—C24—H24B | 109.5 |
C7—C2—C1 | 119.5 (5) | N2—C24—H24C | 109.5 |
C3—C2—C1 | 120.3 (5) | H24A—C24—H24C | 109.5 |
C4—C3—C2 | 119.3 (5) | H24B—C24—H24C | 109.5 |
C4—C3—H3 | 120.3 | O10—C25—N1 | 129.7 (8) |
C2—C3—H3 | 120.3 | O10—C25—H25 | 115.1 |
C5—C4—C3 | 121.1 (5) | N1—C25—H25 | 115.1 |
C5—C4—O6 | 118.5 (5) | N1—C26—H26A | 109.5 |
C3—C4—O6 | 120.2 (5) | N1—C26—H26B | 109.5 |
C4—C5—C6 | 119.6 (5) | H26A—C26—H26B | 109.5 |
C4—C5—H5 | 120.2 | N1—C26—H26C | 109.5 |
C6—C5—H5 | 120.2 | H26A—C26—H26C | 109.5 |
C5—C6—O3 | 124.5 (5) | H26B—C26—H26C | 109.5 |
C5—C6—C7 | 120.0 (5) | N1—C27—H27A | 109.5 |
O3—C6—C7 | 115.5 (5) | N1—C27—H27B | 109.5 |
C2—C7—C6 | 119.7 (5) | H27A—C27—H27B | 109.5 |
C2—C7—H7 | 120.1 | N1—C27—H27C | 109.5 |
C6—C7—H7 | 120.1 | H27A—C27—H27C | 109.5 |
C14—C8—C9 | 121.4 (5) | H27B—C27—H27C | 109.5 |
C14—C8—O3 | 117.2 (5) | C25—N1—C26 | 128.1 (9) |
C9—C8—O3 | 121.1 (5) | C25—N1—C27 | 115.9 (7) |
C10—C9—C8 | 118.7 (5) | C26—N1—C27 | 116.0 (8) |
C10—C9—H9 | 120.6 | C22—N2—C24 | 127.3 (7) |
C8—C9—H9 | 120.6 | C22—N2—C23 | 116.2 (6) |
C9—C10—C11 | 120.5 (5) | C24—N2—C23 | 115.7 (6) |
C9—C10—H10 | 119.8 | C1—O1—Pr1 | 139.7 (3) |
C11—C10—H10 | 119.8 | C1—O2—Pr1ii | 139.4 (3) |
C12—C11—C10 | 120.1 (5) | C6—O3—C8 | 119.2 (4) |
C12—C11—H11 | 119.9 | C13—O4—Pr1v | 90.5 (3) |
C10—C11—H11 | 119.9 | C13—O5—Pr1v | 95.6 (3) |
C11—C12—C14 | 119.7 (5) | C15—O6—C4 | 118.8 (3) |
C11—C12—C13 | 120.7 (5) | C21—O7—Pr1iii | 116.1 (3) |
C14—C12—C13 | 119.5 (5) | C21—O8—Pr1vi | 170.9 (4) |
O4—C13—O5 | 121.9 (5) | C22—O9—Pr1 | 127.2 (4) |
O4—C13—C12 | 120.0 (5) | C25—O10—Pr1 | 132.7 (4) |
O1—C1—C2—C7 | 166.8 (4) | C16—C17—C18—C19 | −1.8 (8) |
O2—C1—C2—C7 | −14.0 (6) | C21—C17—C18—C19 | 177.5 (5) |
O1—C1—C2—C3 | −13.9 (7) | C17—C18—C19—C20 | 1.2 (8) |
O2—C1—C2—C3 | 165.3 (4) | C16—C15—C20—C19 | −1.1 (8) |
C7—C2—C3—C4 | −0.4 (7) | O6—C15—C20—C19 | −177.9 (4) |
C1—C2—C3—C4 | −179.7 (4) | C18—C19—C20—C15 | 0.2 (8) |
C2—C3—C4—C5 | −2.0 (7) | C16—C17—C21—O7 | 11.0 (7) |
C2—C3—C4—O6 | 173.0 (4) | C18—C17—C21—O7 | −168.3 (5) |
C3—C4—C5—C6 | 2.5 (7) | C16—C17—C21—O8 | −169.7 (5) |
O6—C4—C5—C6 | −172.5 (4) | C18—C17—C21—O8 | 11.0 (7) |
C4—C5—C6—O3 | 179.7 (5) | O10—C25—N1—C26 | −179.1 (7) |
C4—C5—C6—C7 | −0.6 (7) | O10—C25—N1—C27 | −1.7 (11) |
C3—C2—C7—C6 | 2.3 (7) | O9—C22—N2—C24 | −176.4 (9) |
C1—C2—C7—C6 | −178.5 (4) | O9—C22—N2—C23 | −7.3 (13) |
C5—C6—C7—C2 | −1.8 (7) | O2—C1—O1—Pr1 | 22.6 (9) |
O3—C6—C7—C2 | 177.9 (4) | C2—C1—O1—Pr1 | −158.4 (3) |
C14—C8—C9—C10 | −3.3 (8) | O1—C1—O2—Pr1ii | −43.3 (8) |
O3—C8—C9—C10 | −177.5 (5) | C2—C1—O2—Pr1ii | 137.6 (4) |
C8—C9—C10—C11 | 1.9 (9) | C5—C6—O3—C8 | −0.2 (7) |
C9—C10—C11—C12 | 1.3 (8) | C7—C6—O3—C8 | −179.9 (5) |
C10—C11—C12—C14 | −3.2 (8) | C14—C8—O3—C6 | 120.4 (5) |
C10—C11—C12—C13 | 173.5 (5) | C9—C8—O3—C6 | −65.2 (7) |
C11—C12—C13—O4 | −164.7 (5) | O5—C13—O4—Pr1v | −7.4 (5) |
C14—C12—C13—O4 | 12.0 (8) | C12—C13—O4—Pr1v | 169.6 (4) |
C11—C12—C13—O5 | 12.4 (8) | O4—C13—O5—Pr1v | 7.7 (6) |
C14—C12—C13—O5 | −170.9 (5) | C12—C13—O5—Pr1v | −169.3 (4) |
C9—C8—C14—C12 | 1.4 (8) | C16—C15—O6—C4 | 24.6 (7) |
O3—C8—C14—C12 | 175.8 (5) | C20—C15—O6—C4 | −158.7 (4) |
C11—C12—C14—C8 | 1.8 (8) | C5—C4—O6—C15 | −101.9 (5) |
C13—C12—C14—C8 | −174.9 (5) | C3—C4—O6—C15 | 83.0 (5) |
C20—C15—C16—C17 | 0.5 (7) | O8—C21—O7—Pr1iii | −19.8 (7) |
O6—C15—C16—C17 | 177.1 (4) | C17—C21—O7—Pr1iii | 159.4 (3) |
C15—C16—C17—C18 | 0.9 (7) | N2—C22—O9—Pr1 | 171.8 (6) |
C15—C16—C17—C21 | −178.4 (4) | N1—C25—O10—Pr1 | 118.2 (8) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+2; (iv) x+1, y, z+1; (v) x−1, y, z−1; (vi) x−1, y, z. |
[Nd(C21H11O8)(C3H7NO)2] | Z = 2 |
Mr = 681.73 | F(000) = 682 |
Triclinic, P1 | Dx = 1.623 Mg m−3 |
a = 10.8669 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1173 (14) Å | Cell parameters from 7465 reflections |
c = 12.4442 (15) Å | θ = 2.9–24.0° |
α = 102.564 (3)° | µ = 1.92 mm−1 |
β = 101.643 (3)° | T = 298 K |
γ = 100.661 (3)° | Block, purple |
V = 1395.4 (3) Å3 | 0.30 × 0.20 × 0.18 mm |
Bruker APEXII CCD diffractometer | 3887 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.081 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.5°, θmin = 2.9° |
Tmin = 0.680, Tmax = 0.746 | h = −13→13 |
22113 measured reflections | k = −13→13 |
5182 independent reflections | l = −15→15 |
Refinement on F2 | 10 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0251P)2 + 1.4693P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
5182 reflections | Δρmax = 0.78 e Å−3 |
365 parameters | Δρmin = −0.60 e Å−3 |
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 data for CP1–CP6 were collected on a Bruker SMART APEXII diffractometer equipped with 1 K CCD instrument, using a graphite monochromator with Mo Kα radiation (λ = 0.71073 Å) at room temperature. Absorption corrections were performed via the SADABS program (Bruker, 2001). All the structures were solved by means of direct methods with SHELXS-97 program (Sheldrick, 2008) and refined on F2 with full-matrix least-squares techniques using the program SHELXL-2014 program (Sheldrick, 2015). After all non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
Nd1 | 0.45655 (3) | 0.44315 (3) | 1.14815 (3) | 0.02371 (10) | |
C1 | 0.2953 (5) | 0.3216 (5) | 0.8651 (5) | 0.0290 (13) | |
C2 | 0.1619 (5) | 0.2547 (4) | 0.7884 (4) | 0.0225 (12) | |
C3 | 0.0744 (5) | 0.1769 (5) | 0.8263 (4) | 0.0274 (13) | |
H3 | 0.096571 | 0.165589 | 0.898977 | 0.033* | |
C4 | −0.0457 (5) | 0.1168 (5) | 0.7545 (4) | 0.0246 (12) | |
C5 | −0.0818 (5) | 0.1354 (5) | 0.6482 (4) | 0.0307 (13) | |
H5 | −0.164655 | 0.096961 | 0.602118 | 0.037* | |
C6 | 0.0054 (5) | 0.2111 (5) | 0.6108 (4) | 0.0302 (13) | |
C7 | 0.1273 (5) | 0.2707 (5) | 0.6799 (4) | 0.0265 (13) | |
H7 | 0.186202 | 0.321536 | 0.653752 | 0.032* | |
C8 | −0.1419 (5) | 0.1801 (6) | 0.4298 (5) | 0.0367 (15) | |
C9 | −0.1831 (6) | 0.0509 (6) | 0.3856 (5) | 0.0412 (15) | |
H9 | −0.131487 | −0.002061 | 0.407303 | 0.049* | |
C10 | −0.3020 (6) | 0.0008 (6) | 0.3085 (5) | 0.0430 (16) | |
H10 | −0.331994 | −0.086695 | 0.279418 | 0.052* | |
C11 | −0.3769 (5) | 0.0806 (5) | 0.2743 (4) | 0.0365 (15) | |
H11 | −0.457905 | 0.046541 | 0.223621 | 0.044* | |
C12 | −0.3313 (5) | 0.2110 (5) | 0.3153 (4) | 0.0309 (13) | |
C13 | −0.4052 (5) | 0.2988 (6) | 0.2711 (4) | 0.0332 (14) | |
C14 | −0.2135 (5) | 0.2618 (5) | 0.3958 (4) | 0.0334 (14) | |
H14 | −0.183457 | 0.349149 | 0.426138 | 0.040* | |
C15 | −0.2017 (4) | 0.0701 (5) | 0.8601 (4) | 0.0235 (12) | |
C16 | −0.2357 (5) | 0.1843 (5) | 0.8705 (4) | 0.0263 (12) | |
H16 | −0.207291 | 0.239301 | 0.829190 | 0.032* | |
C17 | −0.3130 (5) | 0.2172 (5) | 0.9434 (4) | 0.0244 (12) | |
C18 | −0.3532 (5) | 0.1342 (5) | 1.0048 (4) | 0.0331 (14) | |
H18 | −0.403467 | 0.156021 | 1.054759 | 0.040* | |
C19 | −0.3192 (5) | 0.0191 (5) | 0.9921 (4) | 0.0341 (14) | |
H19 | −0.347280 | −0.036284 | 1.033254 | 0.041* | |
C20 | −0.2438 (5) | −0.0143 (5) | 0.9191 (4) | 0.0295 (13) | |
H20 | −0.221851 | −0.092189 | 0.909691 | 0.035* | |
C21 | −0.3549 (5) | 0.3403 (5) | 0.9522 (5) | 0.0322 (14) | |
C22 | 0.1576 (7) | 0.4130 (7) | 1.1920 (6) | 0.068 (2) | |
H22 | 0.178516 | 0.498092 | 1.192262 | 0.082* | |
C23 | −0.0004 (8) | 0.2332 (7) | 1.1843 (8) | 0.102 (3) | |
H23A | 0.012073 | 0.188064 | 1.113746 | 0.153* | |
H23B | −0.090513 | 0.212595 | 1.182989 | 0.153* | |
H23C | 0.048612 | 0.209279 | 1.246078 | 0.153* | |
C24 | −0.0527 (8) | 0.4442 (8) | 1.2059 (9) | 0.129 (4) | |
H24A | −0.119691 | 0.401572 | 1.233836 | 0.193* | |
H24B | −0.089203 | 0.451926 | 1.131477 | 0.193* | |
H24C | −0.013721 | 0.527153 | 1.256493 | 0.193* | |
C25 | 0.5416 (8) | 0.6213 (8) | 1.4238 (7) | 0.083 (3) | |
H25 | 0.601798 | 0.577946 | 1.449926 | 0.100* | |
C26 | 0.6654 (9) | 0.8023 (10) | 1.5771 (7) | 0.166 (6) | |
H26A | 0.631095 | 0.842599 | 1.636864 | 0.249* | |
H26B | 0.722399 | 0.865653 | 1.556840 | 0.249* | |
H26C | 0.712459 | 0.744521 | 1.602761 | 0.249* | |
C27 | 0.4736 (12) | 0.8091 (10) | 1.4384 (10) | 0.154 (4) | |
H27A | 0.431330 | 0.769702 | 1.359524 | 0.232* | |
H27B | 0.521918 | 0.893513 | 1.446639 | 0.232* | |
H27C | 0.409794 | 0.812749 | 1.481529 | 0.232* | |
N1 | 0.5619 (7) | 0.7344 (7) | 1.4803 (5) | 0.079 (2) | |
N2 | 0.0442 (5) | 0.3720 (5) | 1.1998 (5) | 0.0600 (16) | |
O1 | 0.3108 (3) | 0.3236 (4) | 0.9675 (3) | 0.0427 (10) | |
O2 | 0.3774 (3) | 0.3683 (3) | 0.8188 (3) | 0.0359 (9) | |
O3 | −0.0204 (3) | 0.2366 (4) | 0.5056 (3) | 0.0480 (11) | |
O4 | −0.3513 (4) | 0.4132 (4) | 0.2902 (3) | 0.0470 (11) | |
O5 | −0.5196 (3) | 0.2516 (3) | 0.2106 (3) | 0.0386 (10) | |
O6 | −0.1301 (3) | 0.0278 (3) | 0.7852 (3) | 0.0315 (9) | |
O7 | −0.3306 (4) | 0.4014 (3) | 0.8821 (3) | 0.0443 (10) | |
O8 | −0.4097 (4) | 0.3757 (4) | 1.0284 (3) | 0.0472 (11) | |
O9 | 0.2438 (4) | 0.3580 (4) | 1.1843 (3) | 0.0427 (10) | |
O10 | 0.4566 (4) | 0.5595 (4) | 1.3411 (3) | 0.0559 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Nd1 | 0.01696 (16) | 0.02346 (16) | 0.02874 (18) | 0.00682 (12) | 0.00082 (11) | 0.00576 (12) |
C1 | 0.028 (3) | 0.021 (3) | 0.035 (4) | 0.008 (3) | 0.004 (3) | 0.004 (3) |
C2 | 0.022 (3) | 0.021 (3) | 0.026 (3) | 0.011 (2) | 0.006 (2) | 0.006 (2) |
C3 | 0.030 (3) | 0.027 (3) | 0.026 (3) | 0.011 (3) | 0.007 (3) | 0.005 (3) |
C4 | 0.022 (3) | 0.021 (3) | 0.034 (3) | 0.008 (2) | 0.015 (3) | 0.005 (3) |
C5 | 0.015 (3) | 0.035 (3) | 0.039 (4) | 0.007 (3) | −0.001 (3) | 0.011 (3) |
C6 | 0.033 (3) | 0.032 (3) | 0.030 (3) | 0.013 (3) | 0.004 (3) | 0.018 (3) |
C7 | 0.017 (3) | 0.027 (3) | 0.039 (3) | 0.007 (2) | 0.009 (3) | 0.015 (3) |
C8 | 0.027 (3) | 0.057 (4) | 0.032 (3) | 0.012 (3) | 0.003 (3) | 0.025 (3) |
C9 | 0.043 (4) | 0.051 (4) | 0.039 (4) | 0.031 (3) | 0.006 (3) | 0.018 (3) |
C10 | 0.058 (4) | 0.037 (4) | 0.037 (4) | 0.026 (3) | 0.007 (3) | 0.009 (3) |
C11 | 0.041 (4) | 0.039 (4) | 0.027 (3) | 0.012 (3) | 0.001 (3) | 0.008 (3) |
C12 | 0.032 (3) | 0.036 (3) | 0.028 (3) | 0.014 (3) | 0.004 (3) | 0.013 (3) |
C13 | 0.029 (3) | 0.038 (4) | 0.028 (3) | 0.009 (3) | −0.003 (3) | 0.007 (3) |
C14 | 0.035 (3) | 0.032 (3) | 0.034 (3) | 0.008 (3) | 0.002 (3) | 0.014 (3) |
C15 | 0.016 (3) | 0.024 (3) | 0.025 (3) | −0.001 (2) | 0.002 (2) | 0.001 (3) |
C16 | 0.025 (3) | 0.027 (3) | 0.030 (3) | 0.007 (2) | 0.008 (2) | 0.011 (3) |
C17 | 0.020 (3) | 0.025 (3) | 0.027 (3) | 0.005 (2) | 0.005 (2) | 0.004 (3) |
C18 | 0.030 (3) | 0.041 (4) | 0.029 (3) | 0.011 (3) | 0.013 (3) | 0.004 (3) |
C19 | 0.043 (4) | 0.027 (3) | 0.038 (4) | 0.007 (3) | 0.016 (3) | 0.017 (3) |
C20 | 0.030 (3) | 0.021 (3) | 0.038 (3) | 0.010 (3) | 0.006 (3) | 0.008 (3) |
C21 | 0.013 (3) | 0.035 (3) | 0.046 (4) | 0.011 (3) | 0.000 (3) | 0.007 (3) |
C22 | 0.053 (5) | 0.049 (5) | 0.118 (7) | 0.012 (4) | 0.037 (5) | 0.042 (5) |
C23 | 0.075 (6) | 0.074 (6) | 0.159 (9) | 0.009 (5) | 0.054 (6) | 0.020 (6) |
C24 | 0.069 (6) | 0.081 (6) | 0.254 (13) | 0.043 (5) | 0.072 (7) | 0.030 (7) |
C25 | 0.085 (7) | 0.075 (6) | 0.074 (6) | −0.006 (5) | 0.037 (5) | −0.005 (5) |
C26 | 0.132 (8) | 0.202 (12) | 0.066 (6) | −0.107 (8) | 0.023 (6) | −0.038 (7) |
C27 | 0.220 (13) | 0.100 (8) | 0.171 (11) | 0.039 (9) | 0.098 (9) | 0.046 (8) |
N1 | 0.107 (6) | 0.060 (4) | 0.050 (4) | −0.019 (4) | 0.034 (4) | −0.006 (4) |
N2 | 0.036 (3) | 0.061 (4) | 0.096 (5) | 0.021 (3) | 0.033 (3) | 0.023 (3) |
O1 | 0.034 (2) | 0.049 (3) | 0.031 (2) | −0.004 (2) | −0.0055 (19) | 0.005 (2) |
O2 | 0.024 (2) | 0.034 (2) | 0.043 (2) | −0.0035 (18) | 0.0037 (19) | 0.0088 (19) |
O3 | 0.026 (2) | 0.070 (3) | 0.050 (3) | 0.005 (2) | −0.003 (2) | 0.038 (2) |
O4 | 0.038 (2) | 0.030 (2) | 0.059 (3) | 0.004 (2) | −0.015 (2) | 0.012 (2) |
O5 | 0.029 (2) | 0.032 (2) | 0.050 (3) | 0.0066 (19) | −0.004 (2) | 0.015 (2) |
O6 | 0.029 (2) | 0.024 (2) | 0.041 (2) | 0.0017 (17) | 0.0181 (18) | 0.0030 (18) |
O7 | 0.044 (3) | 0.035 (2) | 0.069 (3) | 0.024 (2) | 0.020 (2) | 0.026 (2) |
O8 | 0.035 (2) | 0.053 (3) | 0.055 (3) | 0.022 (2) | 0.017 (2) | 0.003 (2) |
O9 | 0.028 (2) | 0.045 (3) | 0.061 (3) | 0.014 (2) | 0.017 (2) | 0.017 (2) |
O10 | 0.048 (3) | 0.062 (3) | 0.038 (3) | 0.000 (2) | 0.006 (2) | −0.011 (2) |
Nd1—O8i | 2.385 (4) | C15—C16 | 1.373 (7) |
Nd1—O2ii | 2.397 (3) | C15—C20 | 1.380 (7) |
Nd1—O1 | 2.411 (4) | C15—O6 | 1.391 (6) |
Nd1—O7iii | 2.440 (4) | C16—C17 | 1.392 (7) |
Nd1—O5iv | 2.460 (3) | C16—H16 | 0.9300 |
Nd1—O10 | 2.467 (4) | C17—C18 | 1.384 (7) |
Nd1—O9 | 2.498 (4) | C17—C21 | 1.510 (7) |
Nd1—O4iv | 2.573 (3) | C18—C19 | 1.382 (7) |
Nd1—C13iv | 2.864 (5) | C18—H18 | 0.9300 |
C1—O1 | 1.246 (6) | C19—C20 | 1.378 (7) |
C1—O2 | 1.251 (6) | C19—H19 | 0.9300 |
C1—C2 | 1.517 (7) | C20—H20 | 0.9300 |
C2—C7 | 1.386 (6) | C21—O8 | 1.249 (6) |
C2—C3 | 1.388 (7) | C21—O7 | 1.255 (6) |
C3—C4 | 1.377 (7) | C22—O9 | 1.218 (7) |
C3—H3 | 0.9300 | C22—N2 | 1.263 (7) |
C4—C5 | 1.372 (7) | C22—H22 | 0.9300 |
C4—O6 | 1.391 (6) | C23—N2 | 1.487 (8) |
C5—C6 | 1.370 (7) | C23—H23A | 0.9600 |
C5—H5 | 0.9300 | C23—H23B | 0.9600 |
C6—C7 | 1.379 (7) | C23—H23C | 0.9600 |
C6—O3 | 1.384 (6) | C24—N2 | 1.441 (8) |
C7—H7 | 0.9300 | C24—H24A | 0.9600 |
C8—C9 | 1.373 (8) | C24—H24B | 0.9600 |
C8—C14 | 1.381 (7) | C24—H24C | 0.9600 |
C8—O3 | 1.400 (6) | C25—O10 | 1.208 (8) |
C9—C10 | 1.379 (7) | C25—N1 | 1.254 (9) |
C9—H9 | 0.9300 | C25—H25 | 0.9300 |
C10—C11 | 1.387 (7) | C26—N1 | 1.425 (7) |
C10—H10 | 0.9300 | C26—H26A | 0.9600 |
C11—C12 | 1.385 (7) | C26—H26B | 0.9600 |
C11—H11 | 0.9300 | C26—H26C | 0.9600 |
C12—C14 | 1.389 (7) | C27—N1 | 1.471 (11) |
C12—C13 | 1.499 (7) | C27—H27A | 0.9600 |
C13—O4 | 1.247 (6) | C27—H27B | 0.9600 |
C13—O5 | 1.263 (6) | C27—H27C | 0.9600 |
C14—H14 | 0.9300 | ||
O8i—Nd1—O2ii | 76.91 (13) | O5—C13—C12 | 117.8 (5) |
O8i—Nd1—O1 | 74.18 (13) | O4—C13—Nd1v | 63.9 (3) |
O2ii—Nd1—O1 | 126.26 (12) | O5—C13—Nd1v | 58.8 (3) |
O8i—Nd1—O7iii | 123.16 (14) | C12—C13—Nd1v | 169.9 (4) |
O2ii—Nd1—O7iii | 77.99 (13) | C8—C14—C12 | 118.6 (5) |
O1—Nd1—O7iii | 81.38 (13) | C8—C14—H14 | 120.7 |
O8i—Nd1—O5iv | 83.05 (13) | C12—C14—H14 | 120.7 |
O2ii—Nd1—O5iv | 126.82 (12) | C16—C15—C20 | 121.6 (5) |
O1—Nd1—O5iv | 93.27 (13) | C16—C15—O6 | 123.0 (5) |
O7iii—Nd1—O5iv | 149.71 (13) | C20—C15—O6 | 115.3 (4) |
O8i—Nd1—O10 | 144.48 (14) | C15—C16—C17 | 119.5 (5) |
O2ii—Nd1—O10 | 78.46 (13) | C15—C16—H16 | 120.2 |
O1—Nd1—O10 | 141.33 (14) | C17—C16—H16 | 120.2 |
O7iii—Nd1—O10 | 75.32 (14) | C18—C17—C16 | 119.2 (5) |
O5iv—Nd1—O10 | 91.72 (14) | C18—C17—C21 | 120.9 (5) |
O8i—Nd1—O9 | 138.31 (13) | C16—C17—C21 | 119.9 (5) |
O2ii—Nd1—O9 | 144.14 (13) | C19—C18—C17 | 120.4 (5) |
O1—Nd1—O9 | 72.37 (13) | C19—C18—H18 | 119.8 |
O7iii—Nd1—O9 | 75.17 (13) | C17—C18—H18 | 119.8 |
O5iv—Nd1—O9 | 74.81 (12) | C20—C19—C18 | 120.5 (5) |
O10—Nd1—O9 | 72.07 (13) | C20—C19—H19 | 119.7 |
O8i—Nd1—O4iv | 77.58 (13) | C18—C19—H19 | 119.7 |
O2ii—Nd1—O4iv | 75.85 (12) | C19—C20—C15 | 118.7 (5) |
O1—Nd1—O4iv | 137.35 (13) | C19—C20—H20 | 120.6 |
O7iii—Nd1—O4iv | 141.25 (13) | C15—C20—H20 | 120.6 |
O5iv—Nd1—O4iv | 51.75 (11) | O8—C21—O7 | 124.3 (5) |
O10—Nd1—O4iv | 71.82 (14) | O8—C21—C17 | 118.7 (5) |
O9—Nd1—O4iv | 112.51 (13) | O7—C21—C17 | 117.1 (5) |
O8i—Nd1—C13iv | 77.48 (15) | O9—C22—N2 | 129.8 (7) |
O2ii—Nd1—C13iv | 100.95 (15) | O9—C22—H22 | 115.1 |
O1—Nd1—C13iv | 115.36 (15) | N2—C22—H22 | 115.1 |
O7iii—Nd1—C13iv | 157.62 (15) | N2—C23—H23A | 109.5 |
O5iv—Nd1—C13iv | 26.05 (13) | N2—C23—H23B | 109.5 |
O10—Nd1—C13iv | 82.54 (15) | H23A—C23—H23B | 109.5 |
O9—Nd1—C13iv | 95.12 (15) | N2—C23—H23C | 109.5 |
O4iv—Nd1—C13iv | 25.80 (12) | H23A—C23—H23C | 109.5 |
O1—C1—O2 | 127.3 (5) | H23B—C23—H23C | 109.5 |
O1—C1—C2 | 116.1 (5) | N2—C24—H24A | 109.5 |
O2—C1—C2 | 116.6 (5) | N2—C24—H24B | 109.5 |
C7—C2—C3 | 119.9 (5) | H24A—C24—H24B | 109.5 |
C7—C2—C1 | 119.9 (5) | N2—C24—H24C | 109.5 |
C3—C2—C1 | 120.2 (5) | H24A—C24—H24C | 109.5 |
C4—C3—C2 | 118.9 (5) | H24B—C24—H24C | 109.5 |
C4—C3—H3 | 120.5 | O10—C25—N1 | 130.5 (9) |
C2—C3—H3 | 120.5 | O10—C25—H25 | 114.7 |
C5—C4—C3 | 121.4 (5) | N1—C25—H25 | 114.7 |
C5—C4—O6 | 118.2 (4) | N1—C26—H26A | 109.5 |
C3—C4—O6 | 120.1 (5) | N1—C26—H26B | 109.5 |
C6—C5—C4 | 119.4 (5) | H26A—C26—H26B | 109.5 |
C6—C5—H5 | 120.3 | N1—C26—H26C | 109.5 |
C4—C5—H5 | 120.3 | H26A—C26—H26C | 109.5 |
C5—C6—C7 | 120.5 (5) | H26B—C26—H26C | 109.5 |
C5—C6—O3 | 124.3 (5) | N1—C27—H27A | 109.5 |
C7—C6—O3 | 115.1 (5) | N1—C27—H27B | 109.5 |
C6—C7—C2 | 119.8 (5) | H27A—C27—H27B | 109.5 |
C6—C7—H7 | 120.1 | N1—C27—H27C | 109.5 |
C2—C7—H7 | 120.1 | H27A—C27—H27C | 109.5 |
C9—C8—C14 | 121.9 (5) | H27B—C27—H27C | 109.5 |
C9—C8—O3 | 121.6 (5) | C25—N1—C26 | 127.7 (9) |
C14—C8—O3 | 116.3 (5) | C25—N1—C27 | 116.7 (8) |
C8—C9—C10 | 119.1 (5) | C26—N1—C27 | 115.4 (8) |
C8—C9—H9 | 120.4 | C22—N2—C24 | 125.8 (7) |
C10—C9—H9 | 120.4 | C22—N2—C23 | 117.4 (6) |
C9—C10—C11 | 120.1 (5) | C24—N2—C23 | 116.2 (6) |
C9—C10—H10 | 120.0 | C1—O1—Nd1 | 138.5 (3) |
C11—C10—H10 | 120.0 | C1—O2—Nd1ii | 139.9 (3) |
C12—C11—C10 | 120.1 (5) | C6—O3—C8 | 119.1 (4) |
C12—C11—H11 | 119.9 | C13—O4—Nd1v | 90.3 (3) |
C10—C11—H11 | 119.9 | C13—O5—Nd1v | 95.2 (3) |
C11—C12—C14 | 119.9 (5) | C15—O6—C4 | 118.9 (4) |
C11—C12—C13 | 120.8 (5) | C21—O7—Nd1iii | 117.0 (3) |
C14—C12—C13 | 119.2 (5) | C21—O8—Nd1vi | 170.3 (4) |
O4—C13—O5 | 122.3 (5) | C22—O9—Nd1 | 126.6 (4) |
O4—C13—C12 | 119.8 (5) | C25—O10—Nd1 | 133.3 (5) |
O1—C1—C2—C7 | 166.2 (5) | C15—C16—C17—C21 | −177.8 (4) |
O2—C1—C2—C7 | −13.8 (7) | C16—C17—C18—C19 | −1.2 (7) |
O1—C1—C2—C3 | −14.1 (7) | C21—C17—C18—C19 | 177.0 (5) |
O2—C1—C2—C3 | 165.8 (5) | C17—C18—C19—C20 | 0.5 (8) |
C7—C2—C3—C4 | 0.1 (7) | C18—C19—C20—C15 | 0.9 (8) |
C1—C2—C3—C4 | −179.6 (4) | C16—C15—C20—C19 | −1.6 (7) |
C2—C3—C4—C5 | −2.1 (7) | O6—C15—C20—C19 | −177.8 (4) |
C2—C3—C4—O6 | 173.0 (4) | C18—C17—C21—O8 | 10.9 (7) |
C3—C4—C5—C6 | 2.8 (8) | C16—C17—C21—O8 | −170.8 (5) |
O6—C4—C5—C6 | −172.4 (4) | C18—C17—C21—O7 | −169.8 (5) |
C4—C5—C6—C7 | −1.5 (8) | C16—C17—C21—O7 | 8.4 (7) |
C4—C5—C6—O3 | −179.9 (5) | O10—C25—N1—C26 | −179.3 (7) |
C5—C6—C7—C2 | −0.4 (8) | O10—C25—N1—C27 | −3.5 (13) |
O3—C6—C7—C2 | 178.1 (4) | O9—C22—N2—C24 | −178.5 (8) |
C3—C2—C7—C6 | 1.2 (7) | O9—C22—N2—C23 | −8.0 (12) |
C1—C2—C7—C6 | −179.2 (5) | O2—C1—O1—Nd1 | 19.8 (9) |
C14—C8—C9—C10 | −2.8 (9) | C2—C1—O1—Nd1 | −160.3 (3) |
O3—C8—C9—C10 | −178.0 (5) | O1—C1—O2—Nd1ii | −42.6 (9) |
C8—C9—C10—C11 | 1.7 (9) | C2—C1—O2—Nd1ii | 137.5 (4) |
C9—C10—C11—C12 | 1.5 (9) | C5—C6—O3—C8 | −1.5 (8) |
C10—C11—C12—C14 | −3.6 (8) | C7—C6—O3—C8 | 180.0 (5) |
C10—C11—C12—C13 | 174.2 (5) | C9—C8—O3—C6 | −64.0 (7) |
C11—C12—C13—O4 | −164.9 (5) | C14—C8—O3—C6 | 120.6 (5) |
C14—C12—C13—O4 | 13.0 (8) | O5—C13—O4—Nd1v | −7.3 (6) |
C11—C12—C13—O5 | 12.0 (8) | C12—C13—O4—Nd1v | 169.4 (4) |
C14—C12—C13—O5 | −170.2 (5) | O4—C13—O5—Nd1v | 7.7 (6) |
C11—C12—C13—Nd1v | −56 (2) | C12—C13—O5—Nd1v | −169.1 (4) |
C14—C12—C13—Nd1v | 122 (2) | C16—C15—O6—C4 | 27.1 (6) |
C9—C8—C14—C12 | 0.7 (8) | C20—C15—O6—C4 | −156.7 (4) |
O3—C8—C14—C12 | 176.1 (5) | C5—C4—O6—C15 | −104.6 (5) |
C11—C12—C14—C8 | 2.5 (8) | C3—C4—O6—C15 | 80.2 (6) |
C13—C12—C14—C8 | −175.4 (5) | O8—C21—O7—Nd1iii | −20.8 (7) |
C20—C15—C16—C17 | 0.9 (7) | C17—C21—O7—Nd1iii | 160.0 (3) |
O6—C15—C16—C17 | 176.8 (4) | N2—C22—O9—Nd1 | 172.8 (6) |
C15—C16—C17—C18 | 0.5 (7) | N1—C25—O10—Nd1 | 122.5 (8) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+2; (iv) x+1, y, z+1; (v) x−1, y, z−1; (vi) x−1, y, z. |
[Sm(C21H11O8)(C3H7NO)2] | Z = 2 |
Mr = 687.84 | F(000) = 686 |
Triclinic, P1 | Dx = 1.633 Mg m−3 |
a = 10.7827 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9479 (11) Å | Cell parameters from 9862 reflections |
c = 12.7964 (13) Å | θ = 3.4–28.3° |
α = 100.735 (4)° | µ = 2.16 mm−1 |
β = 103.054 (4)° | T = 298 K |
γ = 101.521 (4)° | Block, colourless |
V = 1398.9 (2) Å3 | 0.28 × 0.25 × 0.21 mm |
Bruker APEXII CCD diffractometer | 4574 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.037 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.5°, θmin = 3.0° |
Tmin = 0.602, Tmax = 0.746 | h = −13→13 |
19626 measured reflections | k = −13→13 |
5191 independent reflections | l = −15→15 |
Refinement on F2 | 31 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0154P)2 + 4.2014P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max = 0.001 |
5191 reflections | Δρmax = 2.48 e Å−3 |
373 parameters | Δρmin = −1.11 e Å−3 |
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 data for CP1–CP6 were collected on a Bruker SMART APEXII diffractometer equipped with 1 K CCD instrument, using a graphite monochromator with Mo Kα radiation (λ = 0.71073 Å) at room temperature. Absorption corrections were performed via the SADABS program (Bruker, 2001). All the structures were solved by means of direct methods with SHELXS-97 program (Sheldrick, 2008) and refined on F2 with full-matrix least-squares techniques using the program SHELXL-2014 program (Sheldrick, 2015). After all non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sm1 | 0.45845 (2) | 0.44055 (2) | 1.14456 (2) | 0.02333 (8) | |
C1 | 0.2881 (4) | 0.3222 (4) | 0.8730 (4) | 0.0287 (10) | |
C2 | 0.1542 (4) | 0.2550 (4) | 0.7951 (4) | 0.0246 (9) | |
C3 | 0.0618 (4) | 0.1766 (4) | 0.8297 (4) | 0.0265 (9) | |
H3 | 0.080756 | 0.165147 | 0.901298 | 0.032* | |
C4 | −0.0592 (4) | 0.1160 (4) | 0.7551 (4) | 0.0247 (9) | |
C5 | −0.0912 (4) | 0.1334 (4) | 0.6489 (4) | 0.0301 (10) | |
H5 | −0.174220 | 0.093878 | 0.600799 | 0.036* | |
C6 | 0.0024 (4) | 0.2106 (5) | 0.6161 (4) | 0.0310 (10) | |
C7 | 0.1260 (4) | 0.2715 (4) | 0.6884 (4) | 0.0282 (9) | |
H7 | 0.189008 | 0.322787 | 0.665333 | 0.034* | |
C8 | −0.1385 (5) | 0.1768 (6) | 0.4337 (4) | 0.0396 (12) | |
C9 | −0.1817 (5) | 0.0455 (6) | 0.3909 (4) | 0.0464 (13) | |
H9 | −0.130486 | −0.008101 | 0.415200 | 0.056* | |
C10 | −0.3012 (5) | −0.0060 (5) | 0.3120 (4) | 0.0435 (12) | |
H10 | −0.331538 | −0.094510 | 0.284193 | 0.052* | |
C11 | −0.3758 (5) | 0.0746 (5) | 0.2744 (4) | 0.0366 (11) | |
H11 | −0.457080 | 0.039996 | 0.222266 | 0.044* | |
C12 | −0.3292 (4) | 0.2068 (5) | 0.3145 (4) | 0.0311 (10) | |
C13 | −0.4039 (5) | 0.2956 (5) | 0.2680 (4) | 0.0338 (11) | |
C14 | −0.2100 (5) | 0.2583 (5) | 0.3958 (4) | 0.0350 (11) | |
H14 | −0.179232 | 0.346728 | 0.424227 | 0.042* | |
C15 | −0.2112 (4) | 0.0666 (4) | 0.8611 (3) | 0.0234 (9) | |
C16 | −0.2465 (4) | 0.1817 (4) | 0.8726 (4) | 0.0254 (9) | |
H16 | −0.224046 | 0.238157 | 0.829902 | 0.030* | |
C17 | −0.3163 (4) | 0.2126 (4) | 0.9489 (4) | 0.0257 (9) | |
C18 | −0.3493 (5) | 0.1273 (5) | 1.0111 (4) | 0.0350 (11) | |
H18 | −0.395781 | 0.147310 | 1.062187 | 0.042* | |
C19 | −0.3133 (5) | 0.0122 (5) | 0.9979 (4) | 0.0373 (11) | |
H19 | −0.335959 | −0.044554 | 1.040345 | 0.045* | |
C20 | −0.2444 (4) | −0.0197 (4) | 0.9228 (4) | 0.0319 (10) | |
H20 | −0.220714 | −0.097358 | 0.913733 | 0.038* | |
C21 | −0.3587 (4) | 0.3364 (4) | 0.9597 (4) | 0.0304 (10) | |
C22 | 0.1619 (5) | 0.4151 (6) | 1.1896 (6) | 0.0544 (16) | |
H22 | 0.183025 | 0.501416 | 1.188735 | 0.065* | |
C23 | 0.0016 (7) | 0.2314 (7) | 1.1901 (9) | 0.098 (3) | |
H23A | −0.051166 | 0.188985 | 1.116240 | 0.148* | |
H23B | −0.049711 | 0.218235 | 1.241251 | 0.148* | |
H23C | 0.076618 | 0.196551 | 1.207360 | 0.148* | |
C24 | −0.038 (3) | 0.452 (3) | 1.235 (4) | 0.077 (6) | 0.44 (6) |
H24A | −0.120072 | 0.398867 | 1.235974 | 0.116* | 0.44 (6) |
H24B | 0.006020 | 0.505389 | 1.307944 | 0.116* | 0.44 (6) |
H24C | −0.055139 | 0.505748 | 1.184646 | 0.116* | 0.44 (6) |
C24A | −0.0605 (18) | 0.438 (2) | 1.181 (3) | 0.073 (5) | 0.56 (6) |
H24D | −0.138322 | 0.387405 | 1.192200 | 0.109* | 0.56 (6) |
H24E | −0.033048 | 0.519901 | 1.233466 | 0.109* | 0.56 (6) |
H24F | −0.079107 | 0.449633 | 1.107584 | 0.109* | 0.56 (6) |
C25 | 0.5483 (8) | 0.6194 (8) | 1.4086 (6) | 0.091 (3) | |
H25 | 0.613428 | 0.576227 | 1.425371 | 0.109* | |
C26 | 0.6742 (11) | 0.7789 (11) | 1.5759 (8) | 0.167 (5) | |
H26A | 0.663347 | 0.859373 | 1.612581 | 0.250* | |
H26B | 0.674321 | 0.721630 | 1.624256 | 0.250* | |
H26C | 0.756067 | 0.793079 | 1.556676 | 0.250* | |
C27 | 0.4783 (15) | 0.8072 (12) | 1.4500 (12) | 0.171 (5) | |
H27A | 0.455567 | 0.800011 | 1.371733 | 0.256* | |
H27B | 0.521587 | 0.894834 | 1.488297 | 0.256* | |
H27C | 0.399775 | 0.780558 | 1.472129 | 0.256* | |
N1 | 0.0463 (4) | 0.3698 (5) | 1.1987 (5) | 0.0575 (13) | |
N2 | 0.5682 (7) | 0.7234 (6) | 1.4778 (5) | 0.087 (2) | |
O1 | 0.3034 (3) | 0.3214 (3) | 0.9729 (3) | 0.0402 (8) | |
O2 | 0.3743 (3) | 0.3733 (3) | 0.8321 (3) | 0.0366 (8) | |
O3 | −0.0170 (3) | 0.2332 (4) | 0.5116 (3) | 0.0527 (10) | |
O4 | −0.3472 (3) | 0.4114 (3) | 0.2845 (3) | 0.0455 (9) | |
O5 | −0.5210 (3) | 0.2482 (3) | 0.2098 (3) | 0.0417 (9) | |
O6 | −0.1503 (3) | 0.0250 (3) | 0.7810 (3) | 0.0340 (8) | |
O7 | −0.3367 (3) | 0.4041 (3) | 0.8934 (3) | 0.0421 (8) | |
O8 | −0.4133 (3) | 0.3658 (4) | 1.0334 (3) | 0.0463 (9) | |
O9 | 0.2468 (3) | 0.3585 (3) | 1.1821 (3) | 0.0410 (8) | |
O10 | 0.4648 (4) | 0.5643 (5) | 1.3266 (3) | 0.0640 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sm1 | 0.01767 (11) | 0.02409 (12) | 0.02776 (13) | 0.00667 (8) | 0.00389 (8) | 0.00648 (8) |
C1 | 0.025 (2) | 0.022 (2) | 0.035 (3) | 0.0060 (18) | 0.0010 (19) | 0.0043 (19) |
C2 | 0.021 (2) | 0.019 (2) | 0.031 (2) | 0.0065 (17) | 0.0044 (18) | 0.0030 (17) |
C3 | 0.028 (2) | 0.025 (2) | 0.024 (2) | 0.0045 (18) | 0.0067 (18) | 0.0029 (17) |
C4 | 0.022 (2) | 0.019 (2) | 0.034 (2) | 0.0045 (17) | 0.0139 (18) | 0.0021 (17) |
C5 | 0.019 (2) | 0.036 (3) | 0.033 (2) | 0.0092 (18) | 0.0026 (18) | 0.005 (2) |
C6 | 0.025 (2) | 0.038 (3) | 0.033 (2) | 0.011 (2) | 0.0048 (19) | 0.016 (2) |
C7 | 0.021 (2) | 0.031 (2) | 0.034 (2) | 0.0057 (18) | 0.0076 (18) | 0.0129 (19) |
C8 | 0.028 (3) | 0.064 (4) | 0.032 (3) | 0.016 (2) | 0.005 (2) | 0.024 (2) |
C9 | 0.046 (3) | 0.057 (4) | 0.045 (3) | 0.030 (3) | 0.007 (3) | 0.024 (3) |
C10 | 0.051 (3) | 0.041 (3) | 0.038 (3) | 0.021 (3) | 0.006 (2) | 0.007 (2) |
C11 | 0.039 (3) | 0.039 (3) | 0.029 (2) | 0.014 (2) | 0.003 (2) | 0.008 (2) |
C12 | 0.031 (2) | 0.038 (3) | 0.026 (2) | 0.013 (2) | 0.0036 (19) | 0.013 (2) |
C13 | 0.032 (3) | 0.039 (3) | 0.030 (2) | 0.011 (2) | 0.003 (2) | 0.012 (2) |
C14 | 0.032 (3) | 0.042 (3) | 0.030 (2) | 0.009 (2) | 0.002 (2) | 0.014 (2) |
C15 | 0.017 (2) | 0.025 (2) | 0.025 (2) | 0.0022 (16) | 0.0052 (17) | 0.0013 (17) |
C16 | 0.023 (2) | 0.024 (2) | 0.032 (2) | 0.0047 (17) | 0.0108 (18) | 0.0107 (18) |
C17 | 0.019 (2) | 0.027 (2) | 0.032 (2) | 0.0056 (17) | 0.0082 (18) | 0.0061 (18) |
C18 | 0.037 (3) | 0.037 (3) | 0.038 (3) | 0.009 (2) | 0.022 (2) | 0.012 (2) |
C19 | 0.046 (3) | 0.033 (3) | 0.041 (3) | 0.010 (2) | 0.020 (2) | 0.018 (2) |
C20 | 0.033 (3) | 0.024 (2) | 0.039 (3) | 0.0100 (19) | 0.008 (2) | 0.010 (2) |
C21 | 0.019 (2) | 0.033 (3) | 0.038 (3) | 0.0131 (19) | 0.0021 (19) | 0.005 (2) |
C22 | 0.042 (3) | 0.045 (3) | 0.092 (5) | 0.015 (3) | 0.034 (3) | 0.030 (3) |
C23 | 0.061 (5) | 0.056 (5) | 0.181 (9) | 0.002 (4) | 0.055 (6) | 0.023 (5) |
C24 | 0.055 (9) | 0.067 (9) | 0.112 (14) | 0.031 (7) | 0.026 (10) | 0.009 (11) |
C24A | 0.045 (7) | 0.070 (8) | 0.103 (13) | 0.028 (6) | 0.026 (8) | −0.002 (10) |
C25 | 0.082 (5) | 0.110 (7) | 0.051 (4) | −0.016 (5) | 0.026 (4) | −0.017 (4) |
C26 | 0.158 (9) | 0.160 (10) | 0.088 (6) | −0.105 (8) | 0.031 (6) | −0.040 (6) |
C27 | 0.246 (15) | 0.124 (10) | 0.198 (13) | 0.070 (10) | 0.136 (11) | 0.057 (9) |
N1 | 0.034 (3) | 0.062 (3) | 0.085 (4) | 0.018 (2) | 0.031 (3) | 0.015 (3) |
N2 | 0.111 (5) | 0.075 (4) | 0.045 (3) | −0.032 (3) | 0.033 (3) | −0.014 (3) |
O1 | 0.0313 (18) | 0.045 (2) | 0.0298 (18) | −0.0025 (15) | −0.0036 (14) | 0.0026 (15) |
O2 | 0.0235 (16) | 0.0328 (18) | 0.045 (2) | −0.0056 (14) | 0.0016 (14) | 0.0114 (15) |
O3 | 0.0288 (19) | 0.081 (3) | 0.045 (2) | 0.0029 (18) | −0.0052 (16) | 0.037 (2) |
O4 | 0.039 (2) | 0.0306 (19) | 0.055 (2) | 0.0036 (16) | −0.0100 (17) | 0.0149 (16) |
O5 | 0.0265 (18) | 0.0357 (19) | 0.058 (2) | 0.0062 (14) | −0.0053 (16) | 0.0209 (17) |
O6 | 0.0342 (18) | 0.0236 (16) | 0.0423 (19) | −0.0016 (13) | 0.0220 (15) | −0.0011 (14) |
O7 | 0.039 (2) | 0.0324 (18) | 0.068 (2) | 0.0199 (15) | 0.0211 (18) | 0.0236 (18) |
O8 | 0.039 (2) | 0.059 (2) | 0.047 (2) | 0.0284 (18) | 0.0180 (17) | 0.0025 (18) |
O9 | 0.0252 (17) | 0.048 (2) | 0.060 (2) | 0.0127 (16) | 0.0209 (16) | 0.0226 (18) |
O10 | 0.056 (3) | 0.090 (3) | 0.031 (2) | 0.012 (2) | 0.0085 (19) | −0.013 (2) |
Sm1—O8i | 2.348 (3) | C15—O6 | 1.392 (5) |
Sm1—O2ii | 2.358 (3) | C16—C17 | 1.394 (6) |
Sm1—O1 | 2.392 (3) | C16—H16 | 0.9300 |
Sm1—O7iii | 2.401 (3) | C17—C18 | 1.381 (6) |
Sm1—O5iv | 2.436 (3) | C17—C21 | 1.507 (6) |
Sm1—O10 | 2.446 (4) | C18—C19 | 1.383 (7) |
Sm1—O9 | 2.466 (3) | C18—H18 | 0.9300 |
Sm1—O4iv | 2.546 (3) | C19—C20 | 1.379 (6) |
Sm1—C13iv | 2.834 (5) | C19—H19 | 0.9300 |
C1—O1 | 1.253 (5) | C20—H20 | 0.9300 |
C1—O2 | 1.254 (5) | C21—O8 | 1.246 (5) |
C1—C2 | 1.508 (6) | C21—O7 | 1.258 (6) |
C2—C7 | 1.383 (6) | C22—O9 | 1.214 (6) |
C2—C3 | 1.388 (6) | C22—N1 | 1.286 (7) |
C3—C4 | 1.382 (6) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C23—N1 | 1.471 (8) |
C4—C5 | 1.383 (6) | C23—H23A | 0.9600 |
C4—O6 | 1.395 (5) | C23—H23B | 0.9600 |
C5—C6 | 1.376 (6) | C23—H23C | 0.9600 |
C5—H5 | 0.9300 | C24—N1 | 1.493 (9) |
C6—O3 | 1.383 (5) | C24—H24A | 0.9600 |
C6—C7 | 1.391 (6) | C24—H24B | 0.9600 |
C7—H7 | 0.9300 | C24—H24C | 0.9600 |
C8—C14 | 1.376 (7) | C24A—N1 | 1.489 (9) |
C8—C9 | 1.381 (8) | C24A—H24D | 0.9600 |
C8—O3 | 1.396 (6) | C24A—H24E | 0.9600 |
C9—C10 | 1.381 (7) | C24A—H24F | 0.9600 |
C9—H9 | 0.9300 | C25—O10 | 1.182 (8) |
C10—C11 | 1.387 (7) | C25—N2 | 1.252 (9) |
C10—H10 | 0.9300 | C25—H25 | 0.9300 |
C11—C12 | 1.389 (7) | C26—N2 | 1.429 (11) |
C11—H11 | 0.9300 | C26—H26A | 0.9600 |
C12—C14 | 1.393 (6) | C26—H26B | 0.9600 |
C12—C13 | 1.503 (6) | C26—H26C | 0.9600 |
C13—O4 | 1.247 (6) | C27—N2 | 1.493 (14) |
C13—O5 | 1.261 (5) | C27—H27A | 0.9600 |
C14—H14 | 0.9300 | C27—H27B | 0.9600 |
C15—C16 | 1.380 (6) | C27—H27C | 0.9600 |
C15—C20 | 1.383 (6) | ||
O8i—Sm1—O2ii | 77.41 (13) | C8—C14—C12 | 119.2 (5) |
O8i—Sm1—O1 | 75.19 (12) | C8—C14—H14 | 120.4 |
O2ii—Sm1—O1 | 125.36 (12) | C12—C14—H14 | 120.4 |
O8i—Sm1—O7iii | 123.31 (13) | C16—C15—C20 | 121.6 (4) |
O2ii—Sm1—O7iii | 77.23 (12) | C16—C15—O6 | 122.5 (4) |
O1—Sm1—O7iii | 79.85 (13) | C20—C15—O6 | 115.7 (4) |
O8i—Sm1—O5iv | 81.56 (13) | C15—C16—C17 | 119.3 (4) |
O2ii—Sm1—O5iv | 127.91 (11) | C15—C16—H16 | 120.3 |
O1—Sm1—O5iv | 93.31 (12) | C17—C16—H16 | 120.3 |
O7iii—Sm1—O5iv | 150.42 (12) | C18—C17—C16 | 119.4 (4) |
O8i—Sm1—O10 | 144.62 (14) | C18—C17—C21 | 120.8 (4) |
O2ii—Sm1—O10 | 78.51 (14) | C16—C17—C21 | 119.7 (4) |
O1—Sm1—O10 | 140.18 (13) | C17—C18—C19 | 120.2 (4) |
O7iii—Sm1—O10 | 75.22 (14) | C17—C18—H18 | 119.9 |
O5iv—Sm1—O10 | 93.37 (15) | C19—C18—H18 | 119.9 |
O8i—Sm1—O9 | 137.62 (13) | C20—C19—C18 | 120.9 (4) |
O2ii—Sm1—O9 | 144.36 (12) | C20—C19—H19 | 119.5 |
O1—Sm1—O9 | 71.88 (12) | C18—C19—H19 | 119.5 |
O7iii—Sm1—O9 | 75.97 (11) | C19—C20—C15 | 118.4 (4) |
O5iv—Sm1—O9 | 74.55 (11) | C19—C20—H20 | 120.8 |
O10—Sm1—O9 | 72.26 (14) | C15—C20—H20 | 120.8 |
O8i—Sm1—O4iv | 77.00 (13) | O8—C21—O7 | 123.8 (4) |
O2ii—Sm1—O4iv | 76.60 (11) | O8—C21—C17 | 118.5 (4) |
O1—Sm1—O4iv | 138.47 (12) | O7—C21—C17 | 117.7 (4) |
O7iii—Sm1—O4iv | 141.65 (12) | O9—C22—N1 | 127.8 (5) |
O5iv—Sm1—O4iv | 52.31 (11) | O9—C22—H22 | 116.1 |
O10—Sm1—O4iv | 72.47 (14) | N1—C22—H22 | 116.1 |
O9—Sm1—O4iv | 112.28 (12) | N1—C23—H23A | 109.5 |
O8i—Sm1—C13iv | 76.18 (13) | N1—C23—H23B | 109.5 |
O2ii—Sm1—C13iv | 101.85 (13) | H23A—C23—H23B | 109.5 |
O1—Sm1—C13iv | 115.87 (13) | N1—C23—H23C | 109.5 |
O7iii—Sm1—C13iv | 158.88 (13) | H23A—C23—H23C | 109.5 |
O5iv—Sm1—C13iv | 26.32 (12) | H23B—C23—H23C | 109.5 |
O10—Sm1—C13iv | 83.89 (15) | N1—C24—H24A | 109.5 |
O9—Sm1—C13iv | 94.94 (13) | N1—C24—H24B | 109.5 |
O4iv—Sm1—C13iv | 26.11 (12) | H24A—C24—H24B | 109.5 |
O1—C1—O2 | 125.8 (4) | N1—C24—H24C | 109.5 |
O1—C1—C2 | 117.0 (4) | H24A—C24—H24C | 109.5 |
O2—C1—C2 | 117.1 (4) | H24B—C24—H24C | 109.5 |
C7—C2—C3 | 120.8 (4) | N1—C24A—H24D | 109.5 |
C7—C2—C1 | 118.9 (4) | N1—C24A—H24E | 109.5 |
C3—C2—C1 | 120.3 (4) | H24D—C24A—H24E | 109.5 |
C4—C3—C2 | 118.3 (4) | N1—C24A—H24F | 109.5 |
C4—C3—H3 | 120.9 | H24D—C24A—H24F | 109.5 |
C2—C3—H3 | 120.9 | H24E—C24A—H24F | 109.5 |
C3—C4—C5 | 122.1 (4) | O10—C25—N2 | 133.9 (10) |
C3—C4—O6 | 120.7 (4) | O10—C25—H25 | 113.1 |
C5—C4—O6 | 116.9 (4) | N2—C25—H25 | 113.1 |
C6—C5—C4 | 118.6 (4) | N2—C26—H26A | 109.5 |
C6—C5—H5 | 120.7 | N2—C26—H26B | 109.5 |
C4—C5—H5 | 120.7 | H26A—C26—H26B | 109.5 |
C5—C6—O3 | 123.9 (4) | N2—C26—H26C | 109.5 |
C5—C6—C7 | 120.8 (4) | H26A—C26—H26C | 109.5 |
O3—C6—C7 | 115.2 (4) | H26B—C26—H26C | 109.5 |
C2—C7—C6 | 119.4 (4) | N2—C27—H27A | 109.5 |
C2—C7—H7 | 120.3 | N2—C27—H27B | 109.5 |
C6—C7—H7 | 120.3 | H27A—C27—H27B | 109.5 |
C14—C8—C9 | 121.1 (5) | N2—C27—H27C | 109.5 |
C14—C8—O3 | 117.0 (5) | H27A—C27—H27C | 109.5 |
C9—C8—O3 | 121.7 (5) | H27B—C27—H27C | 109.5 |
C8—C9—C10 | 119.8 (5) | C22—N1—C23 | 119.0 (5) |
C8—C9—H9 | 120.1 | C22—N1—C24A | 123.1 (11) |
C10—C9—H9 | 120.1 | C23—N1—C24A | 115.0 (10) |
C9—C10—C11 | 119.9 (5) | C22—N1—C24 | 123.4 (13) |
C9—C10—H10 | 120.1 | C23—N1—C24 | 116.9 (13) |
C11—C10—H10 | 120.1 | C25—N2—C26 | 128.2 (10) |
C10—C11—C12 | 120.0 (5) | C25—N2—C27 | 116.7 (9) |
C10—C11—H11 | 120.0 | C26—N2—C27 | 114.9 (9) |
C12—C11—H11 | 120.0 | C1—O1—Sm1 | 136.1 (3) |
C11—C12—C14 | 120.0 (4) | C1—O2—Sm1ii | 144.3 (3) |
C11—C12—C13 | 120.6 (4) | C6—O3—C8 | 119.2 (4) |
C14—C12—C13 | 119.4 (4) | C13—O4—Sm1v | 89.9 (3) |
O4—C13—O5 | 122.4 (4) | C13—O5—Sm1v | 94.7 (3) |
O4—C13—C12 | 119.5 (4) | C15—O6—C4 | 118.6 (3) |
O5—C13—C12 | 118.0 (4) | C21—O7—Sm1iii | 121.6 (3) |
O4—C13—Sm1v | 63.9 (2) | C21—O8—Sm1vi | 167.7 (3) |
O5—C13—Sm1v | 59.0 (2) | C22—O9—Sm1 | 127.1 (3) |
C12—C13—Sm1v | 170.1 (3) | C25—O10—Sm1 | 135.3 (5) |
O1—C1—C2—C7 | 169.2 (4) | C17—C18—C19—C20 | 0.0 (8) |
O2—C1—C2—C7 | −11.0 (6) | C18—C19—C20—C15 | 0.4 (7) |
O1—C1—C2—C3 | −11.6 (6) | C16—C15—C20—C19 | −0.6 (7) |
O2—C1—C2—C3 | 168.1 (4) | O6—C15—C20—C19 | −175.5 (4) |
C7—C2—C3—C4 | −0.2 (6) | C18—C17—C21—O8 | 6.7 (7) |
C1—C2—C3—C4 | −179.4 (4) | C16—C17—C21—O8 | −175.3 (4) |
C2—C3—C4—C5 | −1.5 (6) | C18—C17—C21—O7 | −173.3 (4) |
C2—C3—C4—O6 | 172.7 (4) | C16—C17—C21—O7 | 4.6 (6) |
C3—C4—C5—C6 | 2.1 (7) | O9—C22—N1—C23 | −5.7 (11) |
O6—C4—C5—C6 | −172.3 (4) | O9—C22—N1—C24A | −165.4 (18) |
C4—C5—C6—O3 | 178.6 (4) | O9—C22—N1—C24 | 164 (2) |
C4—C5—C6—C7 | −1.0 (7) | O10—C25—N2—C26 | 179.0 (9) |
C3—C2—C7—C6 | 1.3 (7) | O10—C25—N2—C27 | −7.6 (14) |
C1—C2—C7—C6 | −179.6 (4) | O2—C1—O1—Sm1 | 17.6 (8) |
C5—C6—C7—C2 | −0.7 (7) | C2—C1—O1—Sm1 | −162.6 (3) |
O3—C6—C7—C2 | 179.7 (4) | O1—C1—O2—Sm1ii | −45.2 (8) |
C14—C8—C9—C10 | −2.7 (8) | C2—C1—O2—Sm1ii | 135.1 (4) |
O3—C8—C9—C10 | −178.4 (5) | C5—C6—O3—C8 | 0.9 (7) |
C8—C9—C10—C11 | 1.4 (8) | C7—C6—O3—C8 | −179.5 (4) |
C9—C10—C11—C12 | 1.2 (8) | C14—C8—O3—C6 | 117.0 (5) |
C10—C11—C12—C14 | −2.7 (7) | C9—C8—O3—C6 | −67.1 (7) |
C10—C11—C12—C13 | 175.2 (5) | O5—C13—O4—Sm1v | −7.7 (5) |
C11—C12—C13—O4 | −162.7 (5) | C12—C13—O4—Sm1v | 169.5 (4) |
C14—C12—C13—O4 | 15.2 (7) | O4—C13—O5—Sm1v | 8.1 (5) |
C11—C12—C13—O5 | 14.6 (7) | C12—C13—O5—Sm1v | −169.1 (4) |
C14—C12—C13—O5 | −167.6 (4) | C16—C15—O6—C4 | 36.6 (6) |
C9—C8—C14—C12 | 1.2 (7) | C20—C15—O6—C4 | −148.6 (4) |
O3—C8—C14—C12 | 177.1 (4) | C3—C4—O6—C15 | 70.1 (5) |
C11—C12—C14—C8 | 1.5 (7) | C5—C4—O6—C15 | −115.4 (4) |
C13—C12—C14—C8 | −176.4 (4) | O8—C21—O7—Sm1iii | −21.6 (6) |
C20—C15—C16—C17 | 0.6 (6) | C17—C21—O7—Sm1iii | 158.4 (3) |
O6—C15—C16—C17 | 175.1 (4) | O7—C21—O8—Sm1vi | 33.8 (19) |
C15—C16—C17—C18 | −0.3 (6) | C17—C21—O8—Sm1vi | −146.2 (14) |
C15—C16—C17—C21 | −178.3 (4) | N1—C22—O9—Sm1 | 172.8 (5) |
C16—C17—C18—C19 | 0.0 (7) | N2—C25—O10—Sm1 | 140.2 (7) |
C21—C17—C18—C19 | 178.0 (4) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+2; (iv) x+1, y, z+1; (v) x−1, y, z−1; (vi) x−1, y, z. |
[Eu(C21H11O8)(C3H7NO)2] | Z = 2 |
Mr = 689.45 | F(000) = 688 |
Triclinic, P1 | Dx = 1.632 Mg m−3 |
a = 10.7597 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9088 (5) Å | Cell parameters from 9953 reflections |
c = 12.9291 (6) Å | θ = 2.9–27.7° |
α = 100.285 (2)° | µ = 2.29 mm−1 |
β = 103.621 (2)° | T = 298 K |
γ = 101.711 (2)° | Block, colourless |
V = 1402.73 (11) Å3 | 0.20 × 0.20 × 0.18 mm |
Bruker APEXII CCD diffractometer | 4628 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.030 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.5°, θmin = 2.9° |
Tmin = 0.612, Tmax = 0.746 | h = −12→13 |
17116 measured reflections | k = −13→13 |
5200 independent reflections | l = −15→15 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.0161P)2 + 1.6288P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.051 | (Δ/σ)max = 0.002 |
S = 1.07 | Δρmax = 1.31 e Å−3 |
5200 reflections | Δρmin = −0.44 e Å−3 |
364 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
24 restraints | Extinction coefficient: 0.0031 (2) |
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 data for CP1–CP6 were collected on a Bruker SMART APEXII diffractometer equipped with 1 K CCD instrument, using a graphite monochromator with Mo Kα radiation (λ = 0.71073 Å) at room temperature. Absorption corrections were performed via the SADABS program (Bruker, 2001). All the structures were solved by means of direct methods with SHELXS-97 program (Sheldrick, 2008) and refined on F2 with full-matrix least-squares techniques using the program SHELXL-2014 program (Sheldrick, 2015). After all non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
Eu1 | 0.45935 (2) | 0.44029 (2) | 1.14376 (2) | 0.02232 (6) | |
C1 | 0.2868 (3) | 0.3232 (3) | 0.8765 (3) | 0.0291 (7) | |
C2 | 0.1519 (3) | 0.2549 (3) | 0.7970 (2) | 0.0244 (6) | |
C3 | 0.0578 (3) | 0.1765 (3) | 0.8304 (2) | 0.0268 (7) | |
H3 | 0.075950 | 0.165294 | 0.901585 | 0.032* | |
C4 | −0.0639 (3) | 0.1155 (3) | 0.7549 (2) | 0.0262 (7) | |
C5 | −0.0934 (3) | 0.1325 (3) | 0.6494 (3) | 0.0302 (7) | |
H5 | −0.176284 | 0.092312 | 0.600394 | 0.036* | |
C6 | 0.0019 (3) | 0.2100 (3) | 0.6175 (2) | 0.0301 (7) | |
C7 | 0.1250 (3) | 0.2712 (3) | 0.6907 (2) | 0.0286 (7) | |
H7 | 0.189093 | 0.322862 | 0.668742 | 0.034* | |
C8 | −0.1381 (3) | 0.1754 (4) | 0.4348 (3) | 0.0393 (8) | |
C9 | −0.1810 (4) | 0.0438 (4) | 0.3931 (3) | 0.0455 (9) | |
H9 | −0.130062 | −0.009966 | 0.418175 | 0.055* | |
C10 | −0.3011 (4) | −0.0070 (4) | 0.3131 (3) | 0.0441 (9) | |
H10 | −0.331658 | −0.095746 | 0.285226 | 0.053* | |
C11 | −0.3756 (3) | 0.0732 (3) | 0.2746 (3) | 0.0360 (8) | |
H11 | −0.457089 | 0.038464 | 0.222235 | 0.043* | |
C12 | −0.3288 (3) | 0.2056 (3) | 0.3143 (2) | 0.0305 (7) | |
C13 | −0.4029 (3) | 0.2952 (3) | 0.2675 (2) | 0.0317 (7) | |
C14 | −0.2092 (3) | 0.2573 (3) | 0.3959 (3) | 0.0342 (8) | |
H14 | −0.177744 | 0.345955 | 0.423704 | 0.041* | |
C15 | −0.2136 (3) | 0.0665 (3) | 0.8612 (2) | 0.0239 (6) | |
C16 | −0.2493 (3) | 0.1819 (3) | 0.8737 (2) | 0.0252 (6) | |
H16 | −0.228184 | 0.239250 | 0.831377 | 0.030* | |
C17 | −0.3171 (3) | 0.2113 (3) | 0.9502 (2) | 0.0254 (6) | |
C18 | −0.3474 (3) | 0.1257 (3) | 1.0128 (3) | 0.0348 (8) | |
H18 | −0.392245 | 0.145455 | 1.064228 | 0.042* | |
C19 | −0.3113 (4) | 0.0106 (3) | 0.9992 (3) | 0.0392 (8) | |
H19 | −0.332521 | −0.046828 | 1.041397 | 0.047* | |
C20 | −0.2440 (3) | −0.0198 (3) | 0.9236 (3) | 0.0315 (7) | |
H20 | −0.219465 | −0.097165 | 0.914790 | 0.038* | |
C21 | −0.3602 (3) | 0.3353 (3) | 0.9621 (3) | 0.0309 (7) | |
C22 | 0.1636 (4) | 0.4162 (4) | 1.1889 (4) | 0.0548 (11) | |
H22 | 0.183965 | 0.502437 | 1.186227 | 0.066* | |
C23 | 0.0044 (5) | 0.2321 (5) | 1.1929 (6) | 0.099 (2) | |
H23A | −0.026754 | 0.185428 | 1.117468 | 0.149* | |
H23B | −0.065824 | 0.217024 | 1.226779 | 0.149* | |
H23C | 0.077303 | 0.203484 | 1.230251 | 0.149* | |
C24 | −0.0496 (5) | 0.4438 (6) | 1.2033 (7) | 0.122 (3) | |
H24A | −0.127879 | 0.390420 | 1.211146 | 0.183* | |
H24B | −0.014290 | 0.517136 | 1.264658 | 0.183* | |
H24C | −0.071216 | 0.472508 | 1.136853 | 0.183* | |
C25 | 0.5504 (6) | 0.6203 (6) | 1.4041 (4) | 0.0921 (19) | |
H25 | 0.617283 | 0.578243 | 1.418935 | 0.111* | |
C26 | 0.6731 (8) | 0.7716 (8) | 1.5748 (5) | 0.172 (4) | |
H26A | 0.661017 | 0.849999 | 1.613517 | 0.259* | |
H26B | 0.672416 | 0.710292 | 1.619544 | 0.259* | |
H26C | 0.756332 | 0.789292 | 1.558029 | 0.259* | |
C27 | 0.4801 (10) | 0.8044 (8) | 1.4543 (7) | 0.174 (4) | |
H27A | 0.458706 | 0.804393 | 1.377956 | 0.261* | |
H27B | 0.522761 | 0.890570 | 1.497295 | 0.261* | |
H27C | 0.400542 | 0.772707 | 1.473278 | 0.261* | |
N2 | 0.5697 (5) | 0.7207 (4) | 1.4766 (3) | 0.0855 (14) | |
N1 | 0.0479 (3) | 0.3705 (3) | 1.1991 (3) | 0.0570 (9) | |
O1 | 0.3012 (2) | 0.3207 (2) | 0.97493 (18) | 0.0405 (6) | |
O2 | 0.3732 (2) | 0.3758 (2) | 0.83679 (19) | 0.0383 (6) | |
O3 | −0.0155 (2) | 0.2320 (3) | 0.5133 (2) | 0.0527 (7) | |
O4 | −0.3453 (2) | 0.4115 (2) | 0.2834 (2) | 0.0450 (6) | |
O5 | −0.5215 (2) | 0.2482 (2) | 0.2099 (2) | 0.0418 (6) | |
O6 | −0.1567 (2) | 0.0255 (2) | 0.77993 (18) | 0.0354 (5) | |
O7 | −0.3395 (2) | 0.4045 (2) | 0.8971 (2) | 0.0424 (6) | |
O8 | −0.4145 (2) | 0.3624 (2) | 1.03549 (19) | 0.0464 (6) | |
O9 | 0.2491 (2) | 0.3600 (2) | 1.1822 (2) | 0.0419 (6) | |
O10 | 0.4684 (3) | 0.5667 (3) | 1.3222 (2) | 0.0668 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Eu1 | 0.01806 (9) | 0.02349 (9) | 0.02534 (9) | 0.00719 (6) | 0.00419 (6) | 0.00607 (6) |
C1 | 0.0263 (17) | 0.0215 (15) | 0.0352 (18) | 0.0058 (13) | 0.0018 (14) | 0.0054 (13) |
C2 | 0.0201 (15) | 0.0210 (15) | 0.0311 (16) | 0.0079 (12) | 0.0047 (13) | 0.0042 (12) |
C3 | 0.0298 (17) | 0.0261 (16) | 0.0252 (15) | 0.0083 (13) | 0.0088 (13) | 0.0047 (12) |
C4 | 0.0217 (15) | 0.0220 (15) | 0.0352 (17) | 0.0055 (12) | 0.0126 (13) | 0.0012 (13) |
C5 | 0.0174 (15) | 0.0348 (17) | 0.0339 (17) | 0.0083 (13) | 0.0014 (13) | 0.0029 (14) |
C6 | 0.0234 (16) | 0.0380 (18) | 0.0315 (17) | 0.0126 (14) | 0.0039 (13) | 0.0141 (14) |
C7 | 0.0243 (16) | 0.0288 (16) | 0.0362 (17) | 0.0082 (13) | 0.0086 (13) | 0.0149 (14) |
C8 | 0.0276 (18) | 0.062 (2) | 0.0314 (18) | 0.0159 (17) | 0.0032 (14) | 0.0199 (17) |
C9 | 0.049 (2) | 0.057 (2) | 0.041 (2) | 0.034 (2) | 0.0090 (18) | 0.0214 (18) |
C10 | 0.058 (2) | 0.040 (2) | 0.0369 (19) | 0.0247 (18) | 0.0088 (18) | 0.0082 (16) |
C11 | 0.0361 (19) | 0.042 (2) | 0.0283 (17) | 0.0145 (16) | 0.0017 (14) | 0.0086 (14) |
C12 | 0.0292 (17) | 0.0389 (18) | 0.0266 (16) | 0.0130 (15) | 0.0056 (13) | 0.0139 (14) |
C13 | 0.0305 (18) | 0.0376 (19) | 0.0284 (16) | 0.0120 (15) | 0.0045 (14) | 0.0125 (14) |
C14 | 0.0321 (18) | 0.0398 (19) | 0.0300 (17) | 0.0092 (15) | 0.0035 (14) | 0.0131 (14) |
C15 | 0.0156 (14) | 0.0239 (15) | 0.0283 (15) | 0.0023 (12) | 0.0048 (12) | 0.0012 (12) |
C16 | 0.0249 (16) | 0.0241 (15) | 0.0294 (16) | 0.0064 (13) | 0.0094 (13) | 0.0112 (12) |
C17 | 0.0208 (15) | 0.0257 (15) | 0.0308 (16) | 0.0080 (13) | 0.0075 (13) | 0.0066 (13) |
C18 | 0.0404 (19) | 0.0355 (18) | 0.0366 (18) | 0.0113 (15) | 0.0229 (16) | 0.0108 (15) |
C19 | 0.053 (2) | 0.0317 (18) | 0.043 (2) | 0.0111 (17) | 0.0248 (17) | 0.0184 (15) |
C20 | 0.0334 (18) | 0.0230 (16) | 0.0401 (18) | 0.0106 (14) | 0.0098 (15) | 0.0088 (14) |
C21 | 0.0199 (16) | 0.0314 (17) | 0.0392 (18) | 0.0113 (14) | 0.0030 (14) | 0.0047 (15) |
C22 | 0.045 (2) | 0.050 (2) | 0.082 (3) | 0.015 (2) | 0.032 (2) | 0.027 (2) |
C23 | 0.065 (3) | 0.062 (3) | 0.180 (6) | 0.007 (3) | 0.061 (4) | 0.029 (4) |
C24 | 0.069 (4) | 0.087 (4) | 0.240 (8) | 0.048 (3) | 0.076 (5) | 0.035 (5) |
C25 | 0.086 (4) | 0.100 (4) | 0.063 (3) | −0.014 (3) | 0.032 (3) | −0.021 (3) |
C26 | 0.156 (7) | 0.207 (9) | 0.069 (4) | −0.070 (6) | 0.025 (4) | −0.038 (5) |
C27 | 0.255 (11) | 0.145 (7) | 0.182 (9) | 0.084 (7) | 0.135 (8) | 0.053 (6) |
N2 | 0.108 (4) | 0.073 (3) | 0.050 (2) | −0.026 (2) | 0.038 (2) | −0.014 (2) |
N1 | 0.0326 (18) | 0.060 (2) | 0.086 (3) | 0.0185 (16) | 0.0288 (18) | 0.0129 (19) |
O1 | 0.0331 (13) | 0.0456 (14) | 0.0305 (13) | −0.0002 (11) | −0.0020 (10) | 0.0043 (10) |
O2 | 0.0246 (12) | 0.0374 (13) | 0.0463 (14) | −0.0026 (10) | 0.0036 (10) | 0.0138 (11) |
O3 | 0.0284 (13) | 0.084 (2) | 0.0432 (14) | 0.0051 (13) | −0.0030 (11) | 0.0362 (14) |
O4 | 0.0383 (14) | 0.0338 (13) | 0.0517 (15) | 0.0056 (11) | −0.0079 (12) | 0.0136 (11) |
O5 | 0.0249 (12) | 0.0390 (13) | 0.0581 (15) | 0.0079 (10) | −0.0030 (11) | 0.0230 (12) |
O6 | 0.0346 (13) | 0.0242 (11) | 0.0450 (13) | −0.0011 (10) | 0.0235 (11) | −0.0048 (10) |
O7 | 0.0373 (14) | 0.0335 (13) | 0.0703 (17) | 0.0212 (11) | 0.0214 (13) | 0.0252 (12) |
O8 | 0.0419 (14) | 0.0608 (16) | 0.0425 (14) | 0.0307 (13) | 0.0162 (12) | 0.0015 (12) |
O9 | 0.0298 (13) | 0.0508 (15) | 0.0577 (16) | 0.0166 (12) | 0.0229 (12) | 0.0235 (12) |
O10 | 0.0607 (19) | 0.089 (2) | 0.0352 (15) | 0.0139 (17) | 0.0116 (14) | −0.0149 (15) |
Eu1—O8i | 2.337 (2) | C14—H14 | 0.9300 |
Eu1—O2ii | 2.339 (2) | C15—C16 | 1.383 (4) |
Eu1—O7iii | 2.386 (2) | C15—C20 | 1.384 (4) |
Eu1—O1 | 2.386 (2) | C15—O6 | 1.388 (3) |
Eu1—O5iv | 2.428 (2) | C16—C17 | 1.392 (4) |
Eu1—O10 | 2.437 (3) | C16—H16 | 0.9300 |
Eu1—O9 | 2.452 (2) | C17—C18 | 1.379 (4) |
Eu1—O4iv | 2.541 (2) | C17—C21 | 1.511 (4) |
Eu1—C13iv | 2.828 (3) | C18—C19 | 1.381 (5) |
Eu1—C21iii | 3.251 (3) | C18—H18 | 0.9300 |
Eu1—Eu1ii | 4.3681 (4) | C19—C20 | 1.380 (5) |
C1—O1 | 1.251 (4) | C19—H19 | 0.9300 |
C1—O2 | 1.253 (4) | C20—H20 | 0.9300 |
C1—C2 | 1.517 (4) | C21—O8 | 1.249 (4) |
C2—C7 | 1.388 (4) | C21—O7 | 1.254 (4) |
C2—C3 | 1.389 (4) | C22—O9 | 1.215 (4) |
C3—C4 | 1.386 (4) | C22—N1 | 1.290 (5) |
C3—H3 | 0.9300 | C22—H22 | 0.9300 |
C4—C5 | 1.382 (4) | C23—N1 | 1.468 (6) |
C4—O6 | 1.390 (3) | C23—H23A | 0.9600 |
C5—C6 | 1.381 (4) | C23—H23B | 0.9600 |
C5—H5 | 0.9300 | C23—H23C | 0.9600 |
C6—C7 | 1.386 (4) | C24—N1 | 1.447 (6) |
C6—O3 | 1.386 (4) | C24—H24A | 0.9600 |
C7—H7 | 0.9300 | C24—H24B | 0.9600 |
C8—C14 | 1.375 (5) | C24—H24C | 0.9600 |
C8—C9 | 1.379 (5) | C25—O10 | 1.171 (5) |
C8—O3 | 1.403 (4) | C25—N2 | 1.254 (6) |
C9—C10 | 1.386 (5) | C25—H25 | 0.9300 |
C9—H9 | 0.9300 | C26—N2 | 1.411 (7) |
C10—C11 | 1.382 (5) | C26—H26A | 0.9600 |
C10—H10 | 0.9300 | C26—H26B | 0.9600 |
C11—C12 | 1.386 (5) | C26—H26C | 0.9600 |
C11—H11 | 0.9300 | C27—N2 | 1.471 (9) |
C12—C14 | 1.393 (4) | C27—H27A | 0.9600 |
C12—C13 | 1.503 (4) | C27—H27B | 0.9600 |
C13—O4 | 1.250 (4) | C27—H27C | 0.9600 |
C13—O5 | 1.264 (4) | ||
O8i—Eu1—O2ii | 77.31 (9) | C10—C11—C12 | 119.9 (3) |
O8i—Eu1—O7iii | 123.18 (9) | C10—C11—H11 | 120.1 |
O2ii—Eu1—O7iii | 76.96 (8) | C12—C11—H11 | 120.1 |
O8i—Eu1—O1 | 75.45 (9) | C11—C12—C14 | 120.0 (3) |
O2ii—Eu1—O1 | 124.90 (8) | C11—C12—C13 | 120.8 (3) |
O7iii—Eu1—O1 | 79.45 (9) | C14—C12—C13 | 119.2 (3) |
O8i—Eu1—O5iv | 81.13 (9) | O4—C13—O5 | 122.3 (3) |
O2ii—Eu1—O5iv | 128.32 (8) | O4—C13—C12 | 119.7 (3) |
O7iii—Eu1—O5iv | 150.73 (8) | O5—C13—C12 | 118.0 (3) |
O1—Eu1—O5iv | 93.18 (8) | O4—C13—Eu1v | 63.96 (17) |
O8i—Eu1—O10 | 144.62 (10) | O5—C13—Eu1v | 58.82 (16) |
O2ii—Eu1—O10 | 78.83 (10) | C12—C13—Eu1v | 170.0 (2) |
O7iii—Eu1—O10 | 75.40 (10) | C8—C14—C12 | 119.1 (3) |
O1—Eu1—O10 | 139.92 (9) | C8—C14—H14 | 120.4 |
O5iv—Eu1—O10 | 93.79 (10) | C12—C14—H14 | 120.4 |
O8i—Eu1—O9 | 137.42 (9) | C16—C15—C20 | 121.1 (3) |
O2ii—Eu1—O9 | 144.71 (9) | C16—C15—O6 | 122.4 (3) |
O7iii—Eu1—O9 | 76.59 (8) | C20—C15—O6 | 116.3 (3) |
O1—Eu1—O9 | 71.92 (8) | C15—C16—C17 | 119.3 (3) |
O5iv—Eu1—O9 | 74.20 (8) | C15—C16—H16 | 120.4 |
O10—Eu1—O9 | 72.20 (9) | C17—C16—H16 | 120.4 |
O8i—Eu1—O4iv | 76.83 (9) | C18—C17—C16 | 119.8 (3) |
O2ii—Eu1—O4iv | 76.89 (8) | C18—C17—C21 | 120.5 (3) |
O7iii—Eu1—O4iv | 141.79 (8) | C16—C17—C21 | 119.7 (3) |
O1—Eu1—O4iv | 138.71 (8) | C17—C18—C19 | 120.2 (3) |
O5iv—Eu1—O4iv | 52.54 (7) | C17—C18—H18 | 119.9 |
O10—Eu1—O4iv | 72.57 (10) | C19—C18—H18 | 119.9 |
O9—Eu1—O4iv | 111.94 (8) | C20—C19—C18 | 120.6 (3) |
O8i—Eu1—C13iv | 75.70 (9) | C20—C19—H19 | 119.7 |
O2ii—Eu1—C13iv | 102.17 (9) | C18—C19—H19 | 119.7 |
O7iii—Eu1—C13iv | 159.50 (9) | C19—C20—C15 | 119.0 (3) |
O1—Eu1—C13iv | 115.86 (9) | C19—C20—H20 | 120.5 |
O5iv—Eu1—C13iv | 26.44 (8) | C15—C20—H20 | 120.5 |
O10—Eu1—C13iv | 84.30 (10) | O8—C21—O7 | 124.1 (3) |
O9—Eu1—C13iv | 94.68 (9) | O8—C21—C17 | 118.2 (3) |
O4iv—Eu1—C13iv | 26.24 (8) | O7—C21—C17 | 117.7 (3) |
O8i—Eu1—C21iii | 105.10 (9) | O8—C21—Eu1iii | 88.46 (19) |
O2ii—Eu1—C21iii | 65.05 (8) | O7—C21—Eu1iii | 37.72 (15) |
O7iii—Eu1—C21iii | 18.76 (8) | C17—C21—Eu1iii | 150.4 (2) |
O1—Eu1—C21iii | 77.28 (8) | O9—C22—N1 | 127.7 (4) |
O5iv—Eu1—C21iii | 166.59 (8) | O9—C22—H22 | 116.1 |
O10—Eu1—C21iii | 87.79 (10) | N1—C22—H22 | 116.1 |
O9—Eu1—C21iii | 93.69 (8) | N1—C23—H23A | 109.5 |
O4iv—Eu1—C21iii | 139.97 (8) | N1—C23—H23B | 109.5 |
C13iv—Eu1—C21iii | 166.16 (9) | H23A—C23—H23B | 109.5 |
O8i—Eu1—Eu1ii | 51.79 (6) | N1—C23—H23C | 109.5 |
O2ii—Eu1—Eu1ii | 59.28 (6) | H23A—C23—H23C | 109.5 |
O7iii—Eu1—Eu1ii | 71.50 (6) | H23B—C23—H23C | 109.5 |
O1—Eu1—Eu1ii | 66.18 (6) | N1—C24—H24A | 109.5 |
O5iv—Eu1—Eu1ii | 131.28 (6) | N1—C24—H24B | 109.5 |
O10—Eu1—Eu1ii | 130.96 (8) | H24A—C24—H24B | 109.5 |
O9—Eu1—Eu1ii | 130.77 (6) | N1—C24—H24C | 109.5 |
O4iv—Eu1—Eu1ii | 116.42 (6) | H24A—C24—H24C | 109.5 |
C13iv—Eu1—Eu1ii | 126.09 (7) | H24B—C24—H24C | 109.5 |
C21iii—Eu1—Eu1ii | 53.33 (6) | O10—C25—N2 | 135.3 (7) |
O1—C1—O2 | 126.4 (3) | O10—C25—H25 | 112.4 |
O1—C1—C2 | 117.0 (3) | N2—C25—H25 | 112.4 |
O2—C1—C2 | 116.7 (3) | N2—C26—H26A | 109.5 |
C7—C2—C3 | 120.9 (3) | N2—C26—H26B | 109.5 |
C7—C2—C1 | 118.9 (3) | H26A—C26—H26B | 109.5 |
C3—C2—C1 | 120.2 (3) | N2—C26—H26C | 109.5 |
C4—C3—C2 | 118.3 (3) | H26A—C26—H26C | 109.5 |
C4—C3—H3 | 120.9 | H26B—C26—H26C | 109.5 |
C2—C3—H3 | 120.9 | N2—C27—H27A | 109.5 |
C5—C4—C3 | 121.7 (3) | N2—C27—H27B | 109.5 |
C5—C4—O6 | 117.2 (3) | H27A—C27—H27B | 109.5 |
C3—C4—O6 | 120.8 (3) | N2—C27—H27C | 109.5 |
C6—C5—C4 | 119.1 (3) | H27A—C27—H27C | 109.5 |
C6—C5—H5 | 120.5 | H27B—C27—H27C | 109.5 |
C4—C5—H5 | 120.5 | C25—N2—C26 | 128.8 (7) |
C5—C6—C7 | 120.6 (3) | C25—N2—C27 | 117.0 (6) |
C5—C6—O3 | 124.2 (3) | C26—N2—C27 | 114.0 (6) |
C7—C6—O3 | 115.3 (3) | C22—N1—C24 | 124.0 (4) |
C6—C7—C2 | 119.5 (3) | C22—N1—C23 | 118.9 (4) |
C6—C7—H7 | 120.3 | C24—N1—C23 | 116.7 (4) |
C2—C7—H7 | 120.3 | C1—O1—Eu1 | 134.7 (2) |
C14—C8—C9 | 121.5 (3) | C1—O2—Eu1ii | 146.0 (2) |
C14—C8—O3 | 117.1 (3) | C6—O3—C8 | 118.9 (3) |
C9—C8—O3 | 121.2 (3) | C13—O4—Eu1v | 89.79 (18) |
C8—C9—C10 | 119.0 (3) | C13—O5—Eu1v | 94.74 (19) |
C8—C9—H9 | 120.5 | C15—O6—C4 | 118.9 (2) |
C10—C9—H9 | 120.5 | C21—O7—Eu1iii | 123.5 (2) |
C11—C10—C9 | 120.4 (3) | C21—O8—Eu1vi | 166.0 (2) |
C11—C10—H10 | 119.8 | C22—O9—Eu1 | 127.6 (2) |
C9—C10—H10 | 119.8 | C25—O10—Eu1 | 136.5 (4) |
O1—C1—C2—C7 | 170.5 (3) | C18—C19—C20—C15 | −0.3 (5) |
O2—C1—C2—C7 | −10.1 (4) | C16—C15—C20—C19 | 0.1 (5) |
O1—C1—C2—C3 | −10.1 (4) | O6—C15—C20—C19 | −174.3 (3) |
O2—C1—C2—C3 | 169.3 (3) | C18—C17—C21—O8 | 5.5 (4) |
C7—C2—C3—C4 | −0.3 (4) | C16—C17—C21—O8 | −176.2 (3) |
C1—C2—C3—C4 | −179.7 (3) | C18—C17—C21—O7 | −174.3 (3) |
C2—C3—C4—C5 | −1.0 (5) | C16—C17—C21—O7 | 4.0 (4) |
C2—C3—C4—O6 | 173.2 (3) | C18—C17—C21—Eu1iii | −146.6 (3) |
C3—C4—C5—C6 | 1.5 (5) | C16—C17—C21—Eu1iii | 31.7 (5) |
O6—C4—C5—C6 | −172.8 (3) | O10—C25—N2—C26 | 177.5 (6) |
C4—C5—C6—C7 | −0.8 (5) | O10—C25—N2—C27 | −8.2 (10) |
C4—C5—C6—O3 | 178.6 (3) | O9—C22—N1—C24 | −178.1 (5) |
C5—C6—C7—C2 | −0.5 (5) | O9—C22—N1—C23 | −6.0 (8) |
O3—C6—C7—C2 | −179.9 (3) | O2—C1—O1—Eu1 | 17.1 (5) |
C3—C2—C7—C6 | 1.0 (5) | C2—C1—O1—Eu1 | −163.5 (2) |
C1—C2—C7—C6 | −179.6 (3) | O1—C1—O2—Eu1ii | −45.4 (6) |
C14—C8—C9—C10 | −2.6 (6) | C2—C1—O2—Eu1ii | 135.2 (3) |
O3—C8—C9—C10 | −178.0 (3) | C5—C6—O3—C8 | 1.7 (5) |
C8—C9—C10—C11 | 1.0 (6) | C7—C6—O3—C8 | −178.9 (3) |
C9—C10—C11—C12 | 1.5 (5) | C14—C8—O3—C6 | 116.3 (4) |
C10—C11—C12—C14 | −2.5 (5) | C9—C8—O3—C6 | −68.1 (5) |
C10—C11—C12—C13 | 175.2 (3) | O5—C13—O4—Eu1v | −8.2 (3) |
C11—C12—C13—O4 | −162.1 (3) | C12—C13—O4—Eu1v | 169.5 (3) |
C14—C12—C13—O4 | 15.7 (5) | O4—C13—O5—Eu1v | 8.6 (4) |
C11—C12—C13—O5 | 15.7 (5) | C12—C13—O5—Eu1v | −169.1 (2) |
C14—C12—C13—O5 | −166.6 (3) | C16—C15—O6—C4 | 39.4 (4) |
C9—C8—C14—C12 | 1.6 (5) | C20—C15—O6—C4 | −146.2 (3) |
O3—C8—C14—C12 | 177.2 (3) | C5—C4—O6—C15 | −119.1 (3) |
C11—C12—C14—C8 | 1.0 (5) | C3—C4—O6—C15 | 66.5 (4) |
C13—C12—C14—C8 | −176.8 (3) | O8—C21—O7—Eu1iii | −21.9 (4) |
C20—C15—C16—C17 | −0.1 (4) | C17—C21—O7—Eu1iii | 157.9 (2) |
O6—C15—C16—C17 | 174.0 (3) | O7—C21—O8—Eu1vi | 27.3 (12) |
C15—C16—C17—C18 | 0.2 (4) | C17—C21—O8—Eu1vi | −152.5 (8) |
C15—C16—C17—C21 | −178.1 (3) | Eu1iii—C21—O8—Eu1vi | 14.1 (10) |
C16—C17—C18—C19 | −0.3 (5) | N1—C22—O9—Eu1 | 173.1 (3) |
C21—C17—C18—C19 | 178.0 (3) | N2—C25—O10—Eu1 | 145.8 (5) |
C17—C18—C19—C20 | 0.4 (5) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+2; (iv) x+1, y, z+1; (v) x−1, y, z−1; (vi) x−1, y, z. |
[Gd(C21H11O8)(C3H7NO)2] | Z = 2 |
Mr = 694.74 | F(000) = 690 |
Triclinic, P1 | Dx = 1.656 Mg m−3 |
a = 10.722 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.870 (2) Å | Cell parameters from 9862 reflections |
c = 12.949 (3) Å | θ = 3.4–28.3° |
α = 100.12 (3)° | µ = 2.44 mm−1 |
β = 103.89 (3)° | T = 293 K |
γ = 101.79 (3)° | Block, colourless |
V = 1393.4 (5) Å3 | 0.28 × 0.25 × 0.21 mm |
Bruker APEXII CCD diffractometer | 4161 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.047 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.1°, θmin = 2.9° |
Tmin = 0.581, Tmax = 0.746 | h = −11→12 |
16278 measured reflections | k = −12→12 |
4926 independent reflections | l = −15→15 |
Refinement on F2 | 9 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0167P)2 + 3.5767P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max = 0.001 |
4926 reflections | Δρmax = 1.68 e Å−3 |
365 parameters | Δρmin = −1.25 e Å−3 |
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 data for CP1–CP6 were collected on a Bruker SMART APEXII diffractometer equipped with 1 K CCD instrument, using a graphite monochromator with Mo Kα radiation (λ = 0.71073 Å) at room temperature. Absorption corrections were performed via the SADABS program (Bruker, 2001). All the structures were solved by means of direct methods with SHELXS-97 program (Sheldrick, 2008) and refined on F2 with full-matrix least-squares techniques using the program SHELXL-2014 program (Sheldrick, 2015). After all non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.9156 (4) | 0.1399 (4) | −0.0363 (3) | 0.0464 (11) | |
C1 | 0.8615 (5) | 0.1659 (5) | 0.0370 (5) | 0.0329 (13) | |
O1 | 0.8406 (4) | 0.0952 (4) | 0.1016 (3) | 0.0422 (10) | |
Gd1 | −0.04006 (2) | −0.05972 (3) | 0.14329 (2) | 0.02386 (9) | |
C2 | 0.8178 (5) | 0.2887 (5) | 0.0493 (4) | 0.0253 (11) | |
C3 | 0.7513 (5) | 0.3187 (5) | 0.1266 (4) | 0.0259 (11) | |
H3 | 0.731467 | 0.261552 | 0.169533 | 0.031* | |
C4 | 0.7149 (4) | 0.4339 (5) | 0.1390 (4) | 0.0248 (11) | |
C5 | 0.7439 (5) | 0.5208 (5) | 0.0763 (4) | 0.0319 (12) | |
H5 | 0.718927 | 0.598141 | 0.085280 | 0.038* | |
C6 | 0.8104 (6) | 0.4905 (5) | 0.0005 (5) | 0.0396 (14) | |
H6 | 0.830861 | 0.548432 | −0.041704 | 0.048* | |
C7 | 0.8470 (5) | 0.3757 (5) | −0.0136 (5) | 0.0365 (13) | |
H7 | 0.891340 | 0.356373 | −0.065465 | 0.044* | |
C8 | 0.5653 (5) | 0.3843 (5) | 0.2448 (4) | 0.0264 (11) | |
C9 | 0.4437 (5) | 0.3231 (5) | 0.1692 (4) | 0.0289 (12) | |
H9 | 0.425917 | 0.334475 | 0.098089 | 0.035* | |
C10 | 0.3482 (5) | 0.2439 (5) | 0.2018 (4) | 0.0257 (11) | |
C11 | 0.2140 (5) | 0.1769 (5) | 0.1229 (4) | 0.0283 (12) | |
C12 | 0.3747 (5) | 0.2284 (5) | 0.3081 (4) | 0.0291 (12) | |
H12 | 0.310031 | 0.177083 | 0.330087 | 0.035* | |
C13 | 0.4985 (5) | 0.2901 (5) | 0.3813 (4) | 0.0321 (13) | |
C14 | 0.5952 (5) | 0.3678 (5) | 0.3507 (4) | 0.0301 (12) | |
H14 | 0.678477 | 0.408137 | 0.399985 | 0.036* | |
C15 | 0.6381 (5) | 0.3259 (6) | 0.5650 (5) | 0.0404 (14) | |
C16 | 0.6811 (6) | 0.4566 (6) | 0.6061 (5) | 0.0475 (16) | |
H16 | 0.630266 | 0.510608 | 0.580358 | 0.057* | |
C17 | 0.8017 (6) | 0.5079 (6) | 0.6866 (5) | 0.0455 (15) | |
H17 | 0.832468 | 0.596882 | 0.714731 | 0.055* | |
C18 | 0.8764 (6) | 0.4269 (6) | 0.7252 (4) | 0.0384 (14) | |
H18 | 0.958659 | 0.461608 | 0.777365 | 0.046* | |
C19 | 0.8287 (5) | 0.2947 (5) | 0.6861 (4) | 0.0309 (12) | |
C20 | 0.7086 (5) | 0.2427 (6) | 0.6041 (4) | 0.0359 (13) | |
H20 | 0.676712 | 0.153774 | 0.576258 | 0.043* | |
C21 | 0.9030 (5) | 0.2053 (6) | 0.7327 (4) | 0.0340 (13) | |
O10 | −0.0297 (5) | 0.0688 (5) | 0.3199 (4) | 0.0684 (14) | |
C25 | 0.0515 (9) | 0.1211 (9) | 0.4021 (8) | 0.096 (3) | |
H25 | 0.119582 | 0.079888 | 0.416437 | 0.115* | |
N2 | 0.0689 (8) | 0.2194 (7) | 0.4755 (5) | 0.088 (2) | |
C26 | −0.0214 (16) | 0.3033 (13) | 0.4535 (12) | 0.175 (6) | |
H26A | −0.050980 | 0.296448 | 0.376087 | 0.263* | |
H26B | 0.024671 | 0.391333 | 0.490383 | 0.263* | |
H26C | −0.096820 | 0.276680 | 0.479573 | 0.263* | |
C27 | 0.1731 (12) | 0.2692 (13) | 0.5736 (8) | 0.162 (6) | |
H27A | 0.234956 | 0.216458 | 0.576706 | 0.244* | |
H27B | 0.137379 | 0.268961 | 0.634817 | 0.244* | |
H27C | 0.217855 | 0.356171 | 0.576022 | 0.244* | |
O9 | −0.2493 (4) | −0.1390 (4) | 0.1823 (3) | 0.0448 (10) | |
C22 | −0.3356 (6) | −0.0828 (7) | 0.1883 (6) | 0.0557 (18) | |
H22 | −0.316042 | 0.003335 | 0.184426 | 0.067* | |
C23 | −0.4942 (8) | −0.2670 (8) | 0.1950 (9) | 0.101 (3) | |
H23A | −0.499718 | −0.316525 | 0.124242 | 0.152* | |
H23B | −0.580011 | −0.285702 | 0.207667 | 0.152* | |
H23C | −0.431324 | −0.289203 | 0.250335 | 0.152* | |
C24 | −0.5492 (8) | −0.0560 (9) | 0.2027 (11) | 0.125 (4) | |
H24A | −0.530692 | −0.004765 | 0.275669 | 0.188* | |
H24B | −0.636179 | −0.114358 | 0.181744 | 0.188* | |
H24C | −0.545854 | −0.000317 | 0.153010 | 0.188* | |
N1 | −0.4511 (5) | −0.1293 (5) | 0.1994 (5) | 0.0579 (15) | |
O3 | 0.6597 (3) | 0.4746 (3) | 0.2209 (3) | 0.0355 (9) | |
O4 | 0.1273 (3) | 0.1228 (3) | 0.1611 (3) | 0.0383 (9) | |
O5 | 0.1992 (4) | 0.1788 (4) | 0.0242 (3) | 0.0404 (10) | |
O6 | 0.5150 (4) | 0.2684 (5) | 0.4856 (3) | 0.0542 (12) | |
O7 | 0.8446 (4) | 0.0884 (4) | 0.7178 (3) | 0.0452 (10) | |
O8 | 1.0219 (3) | 0.2515 (4) | 0.7906 (3) | 0.0422 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.044 (2) | 0.060 (3) | 0.045 (2) | 0.032 (2) | 0.021 (2) | 0.005 (2) |
C1 | 0.020 (3) | 0.037 (3) | 0.040 (3) | 0.015 (2) | 0.002 (2) | 0.006 (3) |
O1 | 0.038 (2) | 0.033 (2) | 0.070 (3) | 0.0243 (19) | 0.022 (2) | 0.024 (2) |
Gd1 | 0.01894 (13) | 0.02578 (14) | 0.02659 (14) | 0.00730 (10) | 0.00429 (10) | 0.00676 (10) |
C2 | 0.019 (2) | 0.025 (3) | 0.031 (3) | 0.006 (2) | 0.006 (2) | 0.004 (2) |
C3 | 0.026 (3) | 0.025 (3) | 0.026 (3) | 0.002 (2) | 0.009 (2) | 0.007 (2) |
C4 | 0.017 (2) | 0.026 (3) | 0.027 (3) | 0.004 (2) | 0.003 (2) | −0.001 (2) |
C5 | 0.036 (3) | 0.024 (3) | 0.039 (3) | 0.012 (2) | 0.013 (3) | 0.009 (2) |
C6 | 0.053 (4) | 0.029 (3) | 0.045 (4) | 0.012 (3) | 0.022 (3) | 0.018 (3) |
C7 | 0.042 (3) | 0.037 (3) | 0.038 (3) | 0.009 (3) | 0.023 (3) | 0.012 (3) |
C8 | 0.020 (3) | 0.025 (3) | 0.032 (3) | 0.006 (2) | 0.011 (2) | −0.002 (2) |
C9 | 0.028 (3) | 0.028 (3) | 0.029 (3) | 0.007 (2) | 0.007 (2) | 0.003 (2) |
C10 | 0.025 (3) | 0.021 (3) | 0.033 (3) | 0.013 (2) | 0.008 (2) | 0.005 (2) |
C11 | 0.024 (3) | 0.021 (3) | 0.031 (3) | 0.003 (2) | −0.002 (2) | 0.001 (2) |
C12 | 0.021 (3) | 0.032 (3) | 0.038 (3) | 0.009 (2) | 0.007 (2) | 0.015 (2) |
C13 | 0.026 (3) | 0.041 (3) | 0.031 (3) | 0.015 (3) | 0.002 (2) | 0.016 (3) |
C14 | 0.017 (3) | 0.032 (3) | 0.033 (3) | 0.003 (2) | −0.001 (2) | 0.003 (2) |
C15 | 0.033 (3) | 0.060 (4) | 0.032 (3) | 0.015 (3) | 0.003 (3) | 0.023 (3) |
C16 | 0.051 (4) | 0.055 (4) | 0.046 (4) | 0.034 (3) | 0.009 (3) | 0.019 (3) |
C17 | 0.058 (4) | 0.039 (3) | 0.042 (4) | 0.027 (3) | 0.010 (3) | 0.007 (3) |
C18 | 0.038 (3) | 0.043 (3) | 0.030 (3) | 0.013 (3) | −0.002 (3) | 0.011 (3) |
C19 | 0.028 (3) | 0.040 (3) | 0.027 (3) | 0.011 (3) | 0.005 (2) | 0.016 (3) |
C20 | 0.034 (3) | 0.041 (3) | 0.033 (3) | 0.009 (3) | 0.006 (3) | 0.014 (3) |
C21 | 0.029 (3) | 0.040 (3) | 0.032 (3) | 0.009 (3) | 0.005 (3) | 0.011 (3) |
O10 | 0.057 (3) | 0.096 (4) | 0.034 (3) | 0.012 (3) | 0.007 (2) | −0.015 (3) |
C25 | 0.082 (7) | 0.102 (7) | 0.075 (6) | −0.017 (6) | 0.034 (5) | −0.022 (6) |
N2 | 0.108 (6) | 0.078 (5) | 0.049 (4) | −0.024 (4) | 0.034 (4) | −0.016 (4) |
C26 | 0.244 (16) | 0.153 (12) | 0.196 (14) | 0.092 (11) | 0.135 (12) | 0.066 (11) |
C27 | 0.145 (10) | 0.205 (13) | 0.065 (6) | −0.051 (9) | 0.026 (6) | −0.036 (7) |
O9 | 0.031 (2) | 0.057 (3) | 0.062 (3) | 0.021 (2) | 0.025 (2) | 0.028 (2) |
C22 | 0.046 (4) | 0.054 (4) | 0.084 (5) | 0.017 (3) | 0.033 (4) | 0.034 (4) |
C23 | 0.062 (5) | 0.062 (5) | 0.186 (11) | 0.009 (4) | 0.058 (6) | 0.025 (6) |
C24 | 0.068 (6) | 0.085 (7) | 0.244 (14) | 0.042 (5) | 0.076 (8) | 0.025 (8) |
N1 | 0.034 (3) | 0.059 (4) | 0.088 (4) | 0.018 (3) | 0.032 (3) | 0.009 (3) |
O3 | 0.035 (2) | 0.0247 (19) | 0.044 (2) | −0.0014 (17) | 0.0237 (18) | −0.0038 (17) |
O4 | 0.0221 (19) | 0.035 (2) | 0.051 (2) | −0.0043 (17) | 0.0045 (18) | 0.0142 (19) |
O5 | 0.030 (2) | 0.043 (2) | 0.032 (2) | −0.0009 (18) | −0.0045 (17) | −0.0007 (18) |
O6 | 0.029 (2) | 0.087 (3) | 0.042 (2) | 0.005 (2) | −0.0043 (19) | 0.036 (2) |
O7 | 0.037 (2) | 0.035 (2) | 0.052 (3) | 0.0058 (19) | −0.0084 (19) | 0.015 (2) |
O8 | 0.025 (2) | 0.039 (2) | 0.057 (3) | 0.0052 (18) | −0.0037 (19) | 0.023 (2) |
O2—C1 | 1.247 (6) | C15—C16 | 1.365 (8) |
O2—Gd1i | 2.323 (4) | C15—C20 | 1.379 (7) |
C1—O1 | 1.259 (6) | C15—O6 | 1.406 (7) |
C1—C2 | 1.497 (7) | C16—C17 | 1.387 (8) |
O1—Gd1ii | 2.373 (3) | C16—H16 | 0.9300 |
Gd1—O4 | 2.323 (4) | C17—C18 | 1.384 (7) |
Gd1—O5iii | 2.371 (4) | C17—H17 | 0.9300 |
Gd1—O8iv | 2.414 (4) | C18—C19 | 1.379 (8) |
Gd1—O10 | 2.426 (5) | C18—H18 | 0.9300 |
Gd1—O9 | 2.437 (4) | C19—C20 | 1.393 (7) |
Gd1—O7iv | 2.526 (4) | C19—C21 | 1.495 (7) |
Gd1—C21iv | 2.819 (5) | C20—H20 | 0.9300 |
C2—C7 | 1.389 (7) | C21—O7 | 1.255 (6) |
C2—C3 | 1.392 (7) | C21—O8 | 1.260 (6) |
C3—C4 | 1.380 (7) | O10—C25 | 1.164 (9) |
C3—H3 | 0.9300 | C25—N2 | 1.248 (10) |
C4—O3 | 1.384 (6) | C25—H25 | 0.9300 |
C4—C5 | 1.384 (7) | N2—C27 | 1.409 (11) |
C5—C6 | 1.378 (7) | N2—C26 | 1.473 (13) |
C5—H5 | 0.9300 | C26—H26A | 0.9600 |
C6—C7 | 1.379 (7) | C26—H26B | 0.9600 |
C6—H6 | 0.9300 | C26—H26C | 0.9600 |
C7—H7 | 0.9300 | C27—H27A | 0.9600 |
C8—C9 | 1.380 (7) | C27—H27B | 0.9600 |
C8—C14 | 1.383 (7) | C27—H27C | 0.9600 |
C8—O3 | 1.391 (6) | O9—C22 | 1.219 (7) |
C9—C10 | 1.394 (7) | C22—N1 | 1.290 (7) |
C9—H9 | 0.9300 | C22—H22 | 0.9300 |
C10—C12 | 1.384 (7) | C23—N1 | 1.460 (9) |
C10—C11 | 1.500 (7) | C23—H23A | 0.9600 |
C11—O4 | 1.246 (6) | C23—H23B | 0.9600 |
C11—O5 | 1.255 (6) | C23—H23C | 0.9600 |
C12—C13 | 1.386 (7) | C24—N1 | 1.448 (8) |
C12—H12 | 0.9300 | C24—H24A | 0.9600 |
C13—C14 | 1.380 (7) | C24—H24B | 0.9600 |
C13—O6 | 1.388 (6) | C24—H24C | 0.9600 |
C14—H14 | 0.9300 | ||
C1—O2—Gd1i | 165.1 (4) | C14—C13—C12 | 121.3 (5) |
O2—C1—O1 | 124.1 (5) | C14—C13—O6 | 123.9 (5) |
O2—C1—C2 | 118.3 (5) | C12—C13—O6 | 114.8 (5) |
O1—C1—C2 | 117.6 (5) | C13—C14—C8 | 118.4 (5) |
C1—O1—Gd1ii | 124.1 (3) | C13—C14—H14 | 120.8 |
O4—Gd1—O2i | 77.51 (15) | C8—C14—H14 | 120.8 |
O4—Gd1—O5iii | 124.59 (14) | C16—C15—C20 | 121.9 (5) |
O2i—Gd1—O5iii | 75.44 (14) | C16—C15—O6 | 121.6 (5) |
O4—Gd1—O1v | 76.96 (13) | C20—C15—O6 | 116.4 (5) |
O2i—Gd1—O1v | 123.43 (14) | C15—C16—C17 | 119.1 (5) |
O5iii—Gd1—O1v | 79.21 (14) | C15—C16—H16 | 120.4 |
O4—Gd1—O8iv | 128.58 (12) | C17—C16—H16 | 120.4 |
O2i—Gd1—O8iv | 80.69 (14) | C18—C17—C16 | 120.1 (6) |
O5iii—Gd1—O8iv | 93.11 (13) | C18—C17—H17 | 119.9 |
O1v—Gd1—O8iv | 150.69 (13) | C16—C17—H17 | 119.9 |
O4—Gd1—O10 | 78.79 (16) | C19—C18—C17 | 119.9 (5) |
O2i—Gd1—O10 | 144.76 (15) | C19—C18—H18 | 120.0 |
O5iii—Gd1—O10 | 139.80 (15) | C17—C18—H18 | 120.0 |
O1v—Gd1—O10 | 75.17 (16) | C18—C19—C20 | 120.1 (5) |
O8iv—Gd1—O10 | 94.35 (17) | C18—C19—C21 | 120.7 (5) |
O4—Gd1—O9 | 144.87 (14) | C20—C19—C21 | 119.1 (5) |
O2i—Gd1—O9 | 137.10 (15) | C15—C20—C19 | 118.6 (5) |
O5iii—Gd1—O9 | 72.07 (14) | C15—C20—H20 | 120.7 |
O1v—Gd1—O9 | 76.76 (13) | C19—C20—H20 | 120.7 |
O8iv—Gd1—O9 | 73.97 (13) | O7—C21—O8 | 121.7 (5) |
O10—Gd1—O9 | 72.25 (16) | O7—C21—C19 | 119.7 (5) |
O4—Gd1—O7iv | 77.02 (13) | O8—C21—C19 | 118.5 (5) |
O2i—Gd1—O7iv | 76.68 (14) | O7—C21—Gd1iv | 63.6 (3) |
O5iii—Gd1—O7iv | 138.85 (13) | O8—C21—Gd1iv | 58.5 (3) |
O1v—Gd1—O7iv | 141.90 (14) | C19—C21—Gd1iv | 169.8 (4) |
O8iv—Gd1—O7iv | 52.74 (12) | C25—O10—Gd1 | 137.1 (6) |
O10—Gd1—O7iv | 72.84 (16) | O10—C25—N2 | 135.1 (11) |
O9—Gd1—O7iv | 111.76 (13) | O10—C25—H25 | 112.4 |
O4—Gd1—C21iv | 102.48 (15) | N2—C25—H25 | 112.4 |
O2i—Gd1—C21iv | 75.48 (15) | C25—N2—C27 | 128.3 (11) |
O5iii—Gd1—C21iv | 115.87 (15) | C25—N2—C26 | 117.0 (10) |
O1v—Gd1—C21iv | 159.61 (15) | C27—N2—C26 | 114.4 (10) |
O8iv—Gd1—C21iv | 26.43 (14) | N2—C26—H26A | 109.5 |
O10—Gd1—C21iv | 84.68 (17) | N2—C26—H26B | 109.5 |
O9—Gd1—C21iv | 94.31 (14) | H26A—C26—H26B | 109.5 |
O7iv—Gd1—C21iv | 26.44 (13) | N2—C26—H26C | 109.5 |
C7—C2—C3 | 119.4 (5) | H26A—C26—H26C | 109.5 |
C7—C2—C1 | 120.3 (5) | H26B—C26—H26C | 109.5 |
C3—C2—C1 | 120.3 (5) | N2—C27—H27A | 109.5 |
C4—C3—C2 | 119.5 (5) | N2—C27—H27B | 109.5 |
C4—C3—H3 | 120.2 | H27A—C27—H27B | 109.5 |
C2—C3—H3 | 120.2 | N2—C27—H27C | 109.5 |
C3—C4—O3 | 122.2 (5) | H27A—C27—H27C | 109.5 |
C3—C4—C5 | 121.2 (5) | H27B—C27—H27C | 109.5 |
O3—C4—C5 | 116.3 (4) | C22—O9—Gd1 | 127.7 (4) |
C6—C5—C4 | 118.8 (5) | O9—C22—N1 | 127.4 (6) |
C6—C5—H5 | 120.6 | O9—C22—H22 | 116.3 |
C4—C5—H5 | 120.6 | N1—C22—H22 | 116.3 |
C5—C6—C7 | 120.9 (5) | N1—C23—H23A | 109.5 |
C5—C6—H6 | 119.5 | N1—C23—H23B | 109.5 |
C7—C6—H6 | 119.5 | H23A—C23—H23B | 109.5 |
C6—C7—C2 | 120.1 (5) | N1—C23—H23C | 109.5 |
C6—C7—H7 | 119.9 | H23A—C23—H23C | 109.5 |
C2—C7—H7 | 119.9 | H23B—C23—H23C | 109.5 |
C9—C8—C14 | 122.0 (5) | N1—C24—H24A | 109.5 |
C9—C8—O3 | 121.3 (5) | N1—C24—H24B | 109.5 |
C14—C8—O3 | 116.5 (4) | H24A—C24—H24B | 109.5 |
C8—C9—C10 | 118.5 (5) | N1—C24—H24C | 109.5 |
C8—C9—H9 | 120.7 | H24A—C24—H24C | 109.5 |
C10—C9—H9 | 120.7 | H24B—C24—H24C | 109.5 |
C12—C10—C9 | 120.6 (5) | C22—N1—C24 | 123.5 (7) |
C12—C10—C11 | 119.0 (5) | C22—N1—C23 | 119.5 (6) |
C9—C10—C11 | 120.4 (5) | C24—N1—C23 | 116.5 (6) |
O4—C11—O5 | 125.7 (5) | C4—O3—C8 | 118.8 (4) |
O4—C11—C10 | 117.1 (5) | C11—O4—Gd1 | 147.4 (4) |
O5—C11—C10 | 117.2 (5) | C11—O5—Gd1iii | 134.7 (3) |
C10—C12—C13 | 119.2 (5) | C13—O6—C15 | 118.8 (4) |
C10—C12—H12 | 120.4 | C21—O7—Gd1iv | 90.0 (3) |
C13—C12—H12 | 120.4 | C21—O8—Gd1iv | 95.0 (3) |
Gd1i—O2—C1—O1 | −24.2 (19) | C15—C16—C17—C18 | −0.6 (9) |
Gd1i—O2—C1—C2 | 156.0 (13) | C16—C17—C18—C19 | −2.2 (9) |
O2—C1—O1—Gd1ii | 22.3 (7) | C17—C18—C19—C20 | 3.1 (9) |
C2—C1—O1—Gd1ii | −157.8 (3) | C17—C18—C19—C21 | −175.4 (5) |
O2—C1—C2—C7 | −5.1 (7) | C16—C15—C20—C19 | −1.5 (9) |
O1—C1—C2—C7 | 175.0 (5) | O6—C15—C20—C19 | −177.4 (5) |
O2—C1—C2—C3 | 176.9 (5) | C18—C19—C20—C15 | −1.3 (8) |
O1—C1—C2—C3 | −2.9 (7) | C21—C19—C20—C15 | 177.2 (5) |
C7—C2—C3—C4 | 0.3 (7) | C18—C19—C21—O7 | 161.8 (5) |
C1—C2—C3—C4 | 178.3 (4) | C20—C19—C21—O7 | −16.7 (8) |
C2—C3—C4—O3 | −173.9 (4) | C18—C19—C21—O8 | −15.0 (8) |
C2—C3—C4—C5 | −0.3 (7) | C20—C19—C21—O8 | 166.5 (5) |
C3—C4—C5—C6 | 0.0 (8) | C18—C19—C21—Gd1iv | 55 (2) |
O3—C4—C5—C6 | 173.9 (5) | C20—C19—C21—Gd1iv | −123 (2) |
C4—C5—C6—C7 | 0.4 (8) | Gd1—O10—C25—N2 | 149.1 (8) |
C5—C6—C7—C2 | −0.4 (9) | O10—C25—N2—C27 | 178.1 (11) |
C3—C2—C7—C6 | 0.1 (8) | O10—C25—N2—C26 | −9.1 (17) |
C1—C2—C7—C6 | −177.9 (5) | Gd1—O9—C22—N1 | 173.3 (5) |
C14—C8—C9—C10 | 0.9 (7) | O9—C22—N1—C24 | −178.2 (8) |
O3—C8—C9—C10 | −173.4 (4) | O9—C22—N1—C23 | −6.1 (12) |
C8—C9—C10—C12 | 0.7 (7) | C3—C4—O3—C8 | −41.3 (6) |
C8—C9—C10—C11 | 179.2 (4) | C5—C4—O3—C8 | 144.8 (5) |
C12—C10—C11—O4 | 8.4 (7) | C9—C8—O3—C4 | −64.8 (6) |
C9—C10—C11—O4 | −170.1 (5) | C14—C8—O3—C4 | 120.6 (5) |
C12—C10—C11—O5 | −170.7 (5) | O5—C11—O4—Gd1 | 44.5 (9) |
C9—C10—C11—O5 | 10.8 (7) | C10—C11—O4—Gd1 | −134.6 (5) |
C9—C10—C12—C13 | −1.5 (7) | O4—C11—O5—Gd1iii | −15.5 (8) |
C11—C10—C12—C13 | −180.0 (4) | C10—C11—O5—Gd1iii | 163.6 (3) |
C10—C12—C13—C14 | 0.8 (8) | C14—C13—O6—C15 | −1.5 (8) |
C10—C12—C13—O6 | 180.0 (5) | C12—C13—O6—C15 | 179.2 (5) |
C12—C13—C14—C8 | 0.8 (8) | C16—C15—O6—C13 | 68.0 (8) |
O6—C13—C14—C8 | −178.4 (5) | C20—C15—O6—C13 | −116.0 (6) |
C9—C8—C14—C13 | −1.6 (8) | O8—C21—O7—Gd1iv | 7.6 (6) |
O3—C8—C14—C13 | 172.9 (4) | C19—C21—O7—Gd1iv | −169.1 (5) |
C20—C15—C16—C17 | 2.4 (9) | O7—C21—O8—Gd1iv | −8.0 (6) |
O6—C15—C16—C17 | 178.2 (5) | C19—C21—O8—Gd1iv | 168.7 (4) |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z+1; (v) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···Cg | 0.93 | 2.95 | 3.876 (8) | 175 |