Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017458/om6157sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017458/om6157Isup2.hkl |
CCDC reference: 222805
Pr(NO3)3.nH2O (5.03 mmol) was dissolved in 100 ml of anhydrous ethanol and added drop-wise to 2 mmol of 1-aziridineethanol in refluxing 50 ml of a 0.02 M solution of NaOH. Reflux was continued for about one week after which the reaction was filtered and slow evaporation of the filtrate yielded green needle-like crystals of (I) in ca 10% yield. Analysis calculated for C16H42N10O25Pr2: C 18.19, H 4.14, N 13.10%; found: C 17.71, H 4.03, N 12.76%.
All H atoms bonded to C atoms were placed in calculated positions with C—H distances of 0.99 Å and were included in the refinement in riding-motion approximation with Uiso(H) = 1.2Ueq(C). H atoms bonded to O atoms were refined independently with isotropic displacement parameters but the O—H distances were restrained to be 0.840±0.001 Å using the DFIX command in XL (Sheldrick, 2001).
Data collection: COLLECT (Nonius, 1997-2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Pr(C16H36N4O4)(H2O)][Pr(NO3)6]·2H2O | F(000) = 2104 |
Mr = 1056.42 | Dx = 2.028 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7809 reflections |
a = 15.5786 (3) Å | θ = 2.6–27.5° |
b = 14.4453 (3) Å | µ = 2.89 mm−1 |
c = 15.5995 (3) Å | T = 150 K |
β = 99.749 (1)° | Needle, green |
V = 3459.78 (12) Å3 | 0.25 × 0.25 × 0.15 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 7950 independent reflections |
Radiation source: fine-focus sealed tube | 7143 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 9 pixels mm-1 | θmax = 27.7°, θmin = 3.0° |
ϕ scans and ω scans with κ offsets | h = −20→20 |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | k = −18→18 |
Tmin = 0.516, Tmax = 0.651 | l = −20→19 |
27454 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.055 | w = 1/[σ2(Fo2) + 2.2848P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.003 |
7950 reflections | Δρmax = 1.29 e Å−3 |
519 parameters | Δρmin = −0.73 e Å−3 |
10 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00094 (8) |
[Pr(C16H36N4O4)(H2O)][Pr(NO3)6]·2H2O | V = 3459.78 (12) Å3 |
Mr = 1056.42 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.5786 (3) Å | µ = 2.89 mm−1 |
b = 14.4453 (3) Å | T = 150 K |
c = 15.5995 (3) Å | 0.25 × 0.25 × 0.15 mm |
β = 99.749 (1)° |
Nonius KappaCCD diffractometer | 7950 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 7143 reflections with I > 2σ(I) |
Tmin = 0.516, Tmax = 0.651 | Rint = 0.027 |
27454 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | 10 restraints |
wR(F2) = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 1.29 e Å−3 |
7950 reflections | Δρmin = −0.73 e Å−3 |
519 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Pr1 | 0.270460 (8) | 0.305788 (9) | 0.084035 (8) | 0.01522 (5) | |
O1 | 0.22145 (12) | 0.22456 (13) | −0.06762 (12) | 0.0248 (4) | |
O2 | 0.11930 (12) | 0.28642 (13) | −0.00793 (12) | 0.0254 (4) | |
O3 | 0.08706 (14) | 0.22242 (18) | −0.13522 (13) | 0.0421 (6) | |
O4 | 0.15851 (12) | 0.41964 (13) | 0.12722 (11) | 0.0249 (4) | |
O5 | 0.25938 (11) | 0.37961 (12) | 0.23314 (11) | 0.0205 (4) | |
O6 | 0.15349 (15) | 0.46815 (17) | 0.25838 (13) | 0.0440 (6) | |
O7 | 0.36139 (12) | 0.20001 (12) | 0.19763 (12) | 0.0236 (4) | |
O8 | 0.39380 (12) | 0.19300 (12) | 0.06824 (12) | 0.0239 (4) | |
O9 | 0.46479 (12) | 0.10828 (13) | 0.17232 (14) | 0.0335 (5) | |
O10 | 0.23892 (12) | 0.41581 (13) | −0.05463 (12) | 0.0254 (4) | |
O11 | 0.36568 (11) | 0.35064 (13) | −0.03204 (11) | 0.0238 (4) | |
O12 | 0.32180 (13) | 0.42374 (13) | −0.15414 (11) | 0.0305 (4) | |
O13 | 0.33481 (11) | 0.48311 (12) | 0.10241 (11) | 0.0222 (4) | |
O14 | 0.41926 (12) | 0.37560 (12) | 0.16497 (12) | 0.0248 (4) | |
O15 | 0.46585 (12) | 0.51728 (13) | 0.16981 (14) | 0.0325 (5) | |
O16 | 0.21242 (12) | 0.13168 (12) | 0.08448 (11) | 0.0247 (4) | |
O17 | 0.17652 (11) | 0.22005 (11) | 0.18453 (11) | 0.0205 (4) | |
O18 | 0.15631 (13) | 0.07093 (12) | 0.19041 (13) | 0.0304 (4) | |
N1 | 0.14171 (15) | 0.24354 (16) | −0.07150 (15) | 0.0257 (5) | |
N2 | 0.18868 (14) | 0.42432 (15) | 0.20745 (14) | 0.0236 (5) | |
N3 | 0.40802 (14) | 0.16551 (14) | 0.14679 (15) | 0.0218 (5) | |
N4 | 0.30838 (14) | 0.39779 (14) | −0.08228 (13) | 0.0218 (5) | |
N5 | 0.40858 (13) | 0.45930 (14) | 0.14692 (13) | 0.0208 (4) | |
N6 | 0.18113 (13) | 0.13824 (14) | 0.15364 (13) | 0.0198 (4) | |
Pr2 | 0.263766 (8) | 0.252754 (8) | 0.512513 (8) | 0.01379 (5) | |
O19 | 0.32362 (11) | 0.34284 (13) | 0.40165 (11) | 0.0239 (4) | |
H19 | 0.297 | 0.355 | 0.3512 | 0.060 (12)* | |
O20 | 0.12683 (12) | 0.31946 (12) | 0.43661 (13) | 0.0252 (4) | |
H20 | 0.0872 | 0.283 | 0.414 | 0.054 (11)* | |
O21 | 0.16336 (11) | 0.12061 (12) | 0.52086 (11) | 0.0206 (4) | |
H21 | 0.161 | 0.0769 | 0.4851 | 0.044 (10)* | |
O22 | 0.36630 (12) | 0.13051 (13) | 0.48723 (11) | 0.0238 (4) | |
H22 | 0.389 | 0.127 | 0.4423 | 0.050 (11)* | |
O23 | 0.21815 (14) | 0.17606 (13) | 0.36386 (12) | 0.0275 (4) | |
H23A | 0.208 | 0.1201 | 0.352 | 0.040 (10)* | |
H23B | 0.203 | 0.199 | 0.3142 | 0.056 (12)* | |
N7 | 0.39700 (13) | 0.36673 (14) | 0.56845 (13) | 0.0179 (4) | |
N8 | 0.21376 (13) | 0.42023 (14) | 0.57114 (13) | 0.0191 (4) | |
N9 | 0.18713 (13) | 0.23982 (13) | 0.65357 (13) | 0.0166 (4) | |
N10 | 0.37220 (13) | 0.18512 (13) | 0.65391 (13) | 0.0162 (4) | |
C1 | 0.41078 (16) | 0.37834 (19) | 0.41216 (17) | 0.0248 (6) | |
H1A | 0.4097 | 0.4463 | 0.4036 | 0.030* | |
H1B | 0.4424 | 0.3500 | 0.3688 | 0.030* | |
C2 | 0.45574 (16) | 0.35485 (19) | 0.50317 (16) | 0.0226 (5) | |
H2A | 0.4763 | 0.2899 | 0.5045 | 0.027* | |
H2B | 0.5073 | 0.3953 | 0.5190 | 0.027* | |
C3 | 0.36873 (16) | 0.46502 (17) | 0.57034 (17) | 0.0226 (5) | |
H3A | 0.3552 | 0.4888 | 0.5100 | 0.027* | |
H3B | 0.4172 | 0.5024 | 0.6020 | 0.027* | |
C4 | 0.28956 (17) | 0.47648 (17) | 0.61356 (17) | 0.0237 (5) | |
H4A | 0.3048 | 0.4580 | 0.6754 | 0.028* | |
H4B | 0.2727 | 0.5426 | 0.6118 | 0.028* | |
C5 | 0.09467 (17) | 0.41185 (18) | 0.44321 (18) | 0.0252 (6) | |
H5A | 0.0447 | 0.4116 | 0.4748 | 0.030* | |
H5B | 0.0751 | 0.4381 | 0.3845 | 0.030* | |
C6 | 0.16842 (17) | 0.46897 (17) | 0.49207 (17) | 0.0239 (5) | |
H6A | 0.2109 | 0.4827 | 0.4532 | 0.029* | |
H6B | 0.1451 | 0.5286 | 0.5094 | 0.029* | |
C7 | 0.15279 (17) | 0.40807 (17) | 0.63375 (17) | 0.0227 (5) | |
H7A | 0.0938 | 0.3944 | 0.6014 | 0.027* | |
H7B | 0.1496 | 0.4665 | 0.6662 | 0.027* | |
C8 | 0.18102 (17) | 0.33048 (17) | 0.69751 (16) | 0.0206 (5) | |
H8A | 0.2385 | 0.3459 | 0.7321 | 0.025* | |
H8B | 0.1388 | 0.3251 | 0.7381 | 0.025* | |
C9 | 0.09682 (16) | 0.20509 (17) | 0.62361 (16) | 0.0198 (5) | |
H9A | 0.0634 | 0.2523 | 0.5858 | 0.024* | |
H9B | 0.0678 | 0.1958 | 0.6747 | 0.024* | |
C10 | 0.09590 (16) | 0.11508 (17) | 0.57407 (16) | 0.0200 (5) | |
H10A | 0.1072 | 0.0624 | 0.6151 | 0.024* | |
H10B | 0.0384 | 0.1057 | 0.5370 | 0.024* | |
C11 | 0.23535 (16) | 0.17305 (17) | 0.71689 (15) | 0.0190 (5) | |
H11A | 0.2251 | 0.1094 | 0.6940 | 0.023* | |
H11B | 0.2127 | 0.1768 | 0.7724 | 0.023* | |
C12 | 0.33274 (16) | 0.19253 (17) | 0.73391 (16) | 0.0192 (5) | |
H12A | 0.3429 | 0.2556 | 0.7583 | 0.023* | |
H12B | 0.3619 | 0.1481 | 0.7777 | 0.023* | |
C13 | 0.45642 (16) | 0.23601 (17) | 0.66624 (17) | 0.0199 (5) | |
H13A | 0.4915 | 0.2139 | 0.6230 | 0.024* | |
H13B | 0.4893 | 0.2224 | 0.7249 | 0.024* | |
C14 | 0.44356 (16) | 0.33935 (17) | 0.65643 (16) | 0.0213 (5) | |
H14A | 0.4099 | 0.3615 | 0.7008 | 0.026* | |
H14B | 0.5012 | 0.3701 | 0.6674 | 0.026* | |
C15 | 0.38698 (17) | 0.08596 (17) | 0.63622 (16) | 0.0205 (5) | |
H15A | 0.3320 | 0.0514 | 0.6356 | 0.025* | |
H15B | 0.4308 | 0.0606 | 0.6838 | 0.025* | |
C16 | 0.41803 (17) | 0.07113 (18) | 0.55068 (16) | 0.0223 (5) | |
H16A | 0.4805 | 0.0872 | 0.5563 | 0.027* | |
H16B | 0.4104 | 0.0055 | 0.5326 | 0.027* | |
O1W | 0.00051 (13) | 0.20477 (14) | 0.37623 (13) | 0.0271 (4) | |
H1WA | 0.020 | 0.1522 | 0.367 | 0.038 (10)* | |
H1WB | −0.0401 | 0.195 | 0.4042 | 0.045 (11)* | |
O2W | 0.46088 (16) | 0.11367 (19) | 0.36595 (15) | 0.0415 (5) | |
H2WA | 0.493 | 0.160 | 0.364 | 0.15 (3)* | |
H2WB | 0.430 | 0.100 | 0.3180 | 0.093 (18)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pr1 | 0.01556 (8) | 0.01593 (7) | 0.01463 (8) | 0.00102 (5) | 0.00386 (5) | 0.00002 (5) |
O1 | 0.0227 (10) | 0.0319 (10) | 0.0203 (9) | −0.0033 (8) | 0.0051 (7) | −0.0050 (8) |
O2 | 0.0208 (9) | 0.0348 (11) | 0.0213 (9) | −0.0006 (8) | 0.0051 (7) | −0.0029 (8) |
O3 | 0.0292 (11) | 0.0722 (16) | 0.0228 (11) | −0.0217 (11) | −0.0013 (9) | −0.0093 (10) |
O4 | 0.0259 (9) | 0.0293 (10) | 0.0192 (9) | 0.0073 (8) | 0.0029 (7) | −0.0005 (7) |
O5 | 0.0223 (9) | 0.0210 (9) | 0.0181 (8) | 0.0006 (7) | 0.0030 (7) | 0.0004 (7) |
O6 | 0.0464 (13) | 0.0584 (15) | 0.0302 (11) | 0.0219 (11) | 0.0152 (10) | −0.0097 (10) |
O7 | 0.0235 (9) | 0.0250 (9) | 0.0233 (9) | 0.0034 (7) | 0.0066 (8) | 0.0030 (7) |
O8 | 0.0238 (10) | 0.0237 (9) | 0.0256 (10) | 0.0024 (7) | 0.0083 (8) | 0.0008 (7) |
O9 | 0.0208 (9) | 0.0272 (10) | 0.0534 (13) | 0.0078 (8) | 0.0087 (9) | 0.0135 (9) |
O10 | 0.0235 (9) | 0.0255 (10) | 0.0269 (10) | 0.0020 (8) | 0.0037 (8) | 0.0028 (8) |
O11 | 0.0199 (9) | 0.0298 (10) | 0.0220 (9) | 0.0004 (8) | 0.0042 (7) | 0.0040 (8) |
O12 | 0.0427 (12) | 0.0339 (11) | 0.0144 (9) | −0.0132 (9) | 0.0034 (8) | 0.0033 (8) |
O13 | 0.0219 (9) | 0.0210 (9) | 0.0233 (9) | 0.0008 (7) | 0.0030 (7) | 0.0037 (7) |
O14 | 0.0248 (10) | 0.0171 (9) | 0.0319 (10) | 0.0029 (7) | 0.0033 (8) | 0.0012 (7) |
O15 | 0.0232 (10) | 0.0253 (10) | 0.0491 (13) | −0.0078 (8) | 0.0064 (9) | −0.0068 (9) |
O16 | 0.0307 (10) | 0.0226 (9) | 0.0227 (9) | 0.0016 (8) | 0.0097 (8) | −0.0048 (7) |
O17 | 0.0263 (10) | 0.0141 (8) | 0.0221 (9) | −0.0002 (7) | 0.0072 (7) | −0.0027 (7) |
O18 | 0.0361 (11) | 0.0197 (9) | 0.0372 (11) | −0.0063 (8) | 0.0119 (9) | 0.0036 (8) |
N1 | 0.0242 (12) | 0.0336 (13) | 0.0194 (11) | −0.0094 (9) | 0.0043 (10) | 0.0002 (9) |
N2 | 0.0261 (11) | 0.0240 (11) | 0.0223 (11) | 0.0041 (9) | 0.0087 (9) | −0.0002 (9) |
N3 | 0.0177 (10) | 0.0158 (10) | 0.0319 (12) | −0.0016 (8) | 0.0042 (9) | 0.0027 (9) |
N4 | 0.0272 (12) | 0.0195 (11) | 0.0180 (11) | −0.0072 (9) | 0.0015 (9) | −0.0015 (8) |
N5 | 0.0200 (10) | 0.0207 (11) | 0.0231 (11) | −0.0011 (8) | 0.0081 (9) | −0.0031 (8) |
N6 | 0.0158 (10) | 0.0191 (10) | 0.0243 (11) | −0.0013 (8) | 0.0032 (8) | 0.0005 (9) |
Pr2 | 0.01328 (8) | 0.01476 (8) | 0.01358 (8) | −0.00021 (4) | 0.00302 (5) | 0.00062 (4) |
O19 | 0.0199 (9) | 0.0321 (10) | 0.0198 (9) | −0.0048 (8) | 0.0036 (7) | 0.0073 (8) |
O20 | 0.0196 (9) | 0.0204 (9) | 0.0335 (11) | 0.0023 (7) | −0.0015 (8) | 0.0010 (8) |
O21 | 0.0233 (9) | 0.0180 (9) | 0.0225 (9) | −0.0032 (7) | 0.0094 (7) | −0.0048 (7) |
O22 | 0.0257 (10) | 0.0288 (10) | 0.0176 (9) | 0.0084 (8) | 0.0051 (7) | 0.0001 (8) |
O23 | 0.0411 (12) | 0.0244 (10) | 0.0154 (9) | −0.0039 (9) | 0.0005 (8) | −0.0024 (8) |
N7 | 0.0164 (10) | 0.0176 (10) | 0.0203 (10) | −0.0022 (8) | 0.0048 (8) | −0.0004 (8) |
N8 | 0.0189 (10) | 0.0152 (10) | 0.0248 (11) | −0.0001 (8) | 0.0086 (8) | 0.0024 (8) |
N9 | 0.0168 (10) | 0.0164 (10) | 0.0170 (10) | −0.0009 (8) | 0.0042 (8) | −0.0004 (8) |
N10 | 0.0157 (10) | 0.0168 (10) | 0.0161 (10) | −0.0013 (8) | 0.0028 (8) | −0.0016 (8) |
C1 | 0.0189 (12) | 0.0310 (14) | 0.0259 (13) | −0.0004 (11) | 0.0076 (10) | 0.0068 (11) |
C2 | 0.0165 (12) | 0.0275 (13) | 0.0251 (13) | −0.0020 (10) | 0.0072 (10) | 0.0037 (11) |
C3 | 0.0214 (12) | 0.0165 (12) | 0.0304 (14) | −0.0031 (10) | 0.0063 (11) | 0.0006 (10) |
C4 | 0.0249 (13) | 0.0161 (12) | 0.0306 (14) | −0.0043 (10) | 0.0056 (11) | −0.0036 (10) |
C5 | 0.0197 (13) | 0.0233 (13) | 0.0330 (15) | 0.0054 (10) | 0.0052 (11) | 0.0060 (11) |
C6 | 0.0262 (13) | 0.0173 (12) | 0.0298 (14) | 0.0034 (10) | 0.0094 (11) | 0.0047 (10) |
C7 | 0.0256 (13) | 0.0176 (12) | 0.0281 (14) | 0.0031 (10) | 0.0136 (11) | −0.0006 (10) |
C8 | 0.0257 (13) | 0.0183 (12) | 0.0199 (12) | −0.0014 (10) | 0.0100 (10) | −0.0043 (10) |
C9 | 0.0149 (12) | 0.0223 (13) | 0.0224 (13) | −0.0025 (9) | 0.0036 (10) | 0.0003 (10) |
C10 | 0.0178 (12) | 0.0204 (12) | 0.0218 (12) | −0.0038 (9) | 0.0030 (10) | 0.0030 (10) |
C11 | 0.0228 (13) | 0.0200 (12) | 0.0143 (11) | −0.0023 (10) | 0.0033 (10) | 0.0022 (9) |
C12 | 0.0191 (12) | 0.0228 (13) | 0.0154 (12) | −0.0005 (9) | 0.0023 (9) | −0.0007 (9) |
C13 | 0.0146 (12) | 0.0238 (13) | 0.0206 (13) | −0.0028 (10) | 0.0009 (10) | 0.0014 (10) |
C14 | 0.0188 (12) | 0.0223 (13) | 0.0218 (13) | −0.0041 (10) | 0.0008 (10) | −0.0002 (10) |
C15 | 0.0244 (13) | 0.0170 (12) | 0.0197 (12) | 0.0002 (10) | 0.0023 (10) | 0.0010 (9) |
C16 | 0.0229 (13) | 0.0215 (13) | 0.0214 (13) | 0.0045 (10) | 0.0001 (10) | 0.0005 (10) |
O1W | 0.0222 (10) | 0.0304 (11) | 0.0284 (10) | −0.0013 (9) | 0.0033 (8) | 0.0019 (8) |
O2W | 0.0379 (13) | 0.0591 (16) | 0.0292 (12) | 0.0028 (12) | 0.0104 (10) | 0.0008 (11) |
Pr1—O2 | 2.5568 (18) | N8—C6 | 1.490 (3) |
Pr1—O8 | 2.5628 (18) | N8—C4 | 1.493 (3) |
Pr1—O4 | 2.5687 (18) | N9—C8 | 1.489 (3) |
Pr1—O7 | 2.5751 (17) | N9—C11 | 1.490 (3) |
Pr1—O5 | 2.5910 (17) | N9—C9 | 1.492 (3) |
Pr1—O11 | 2.6093 (18) | N10—C15 | 1.484 (3) |
Pr1—O17 | 2.6287 (17) | N10—C12 | 1.485 (3) |
Pr1—O1 | 2.6354 (18) | N10—C13 | 1.488 (3) |
Pr1—O14 | 2.6445 (18) | C1—C2 | 1.511 (4) |
Pr1—O10 | 2.6620 (18) | C1—H1A | 0.9900 |
Pr1—O16 | 2.6730 (18) | C1—H1B | 0.9900 |
Pr1—O13 | 2.7478 (17) | C2—H2A | 0.9900 |
O1—N1 | 1.264 (3) | C2—H2B | 0.9900 |
O2—N1 | 1.267 (3) | C3—C4 | 1.512 (4) |
O3—N1 | 1.233 (3) | C3—H3A | 0.9900 |
O4—N2 | 1.262 (3) | C3—H3B | 0.9900 |
O5—N2 | 1.281 (3) | C4—H4A | 0.9900 |
O6—N2 | 1.217 (3) | C4—H4B | 0.9900 |
O7—N3 | 1.265 (3) | C5—C6 | 1.512 (4) |
O8—N3 | 1.271 (3) | C5—H5A | 0.9900 |
O9—N3 | 1.227 (3) | C5—H5B | 0.9900 |
O10—N4 | 1.258 (3) | C6—H6A | 0.9900 |
O11—N4 | 1.280 (3) | C6—H6B | 0.9900 |
O12—N4 | 1.233 (3) | C7—C8 | 1.513 (3) |
O13—N5 | 1.285 (3) | C7—H7A | 0.9900 |
O14—N5 | 1.246 (3) | C7—H7B | 0.9900 |
O15—N5 | 1.232 (3) | C8—H8A | 0.9900 |
O16—N6 | 1.261 (3) | C8—H8B | 0.9900 |
O17—N6 | 1.283 (3) | C9—C10 | 1.511 (3) |
O18—N6 | 1.224 (3) | C9—H9A | 0.9900 |
Pr2—O20 | 2.4548 (18) | C9—H9B | 0.9900 |
Pr2—O22 | 2.4573 (18) | C10—H10A | 0.9900 |
Pr2—O19 | 2.4698 (17) | C10—H10B | 0.9900 |
Pr2—O21 | 2.4853 (17) | C11—C12 | 1.522 (3) |
Pr2—O23 | 2.5596 (18) | C11—H11A | 0.9900 |
Pr2—N7 | 2.677 (2) | C11—H11B | 0.9900 |
Pr2—N9 | 2.682 (2) | C12—H12A | 0.9900 |
Pr2—N10 | 2.7224 (19) | C12—H12B | 0.9900 |
Pr2—N8 | 2.745 (2) | C13—C14 | 1.510 (3) |
O19—C1 | 1.435 (3) | C13—H13A | 0.9900 |
O19—H19 | 0.8400 | C13—H13B | 0.9900 |
O20—C5 | 1.435 (3) | C14—H14A | 0.9900 |
O20—H20 | 0.8400 | C14—H14B | 0.9900 |
O21—C10 | 1.447 (3) | C15—C16 | 1.510 (3) |
O21—H21 | 0.8400 | C15—H15A | 0.9900 |
O22—C16 | 1.447 (3) | C15—H15B | 0.9900 |
O22—H22 | 0.8400 | C16—H16A | 0.9900 |
O23—H23A | 0.8400 | C16—H16B | 0.9900 |
O23—H23B | 0.8400 | O1W—H1WA | 0.8400 |
N7—C3 | 1.488 (3) | O1W—H1WB | 0.8400 |
N7—C2 | 1.490 (3) | O2W—H2WA | 0.8400 |
N7—C14 | 1.493 (3) | O2W—H2WB | 0.8400 |
N8—C7 | 1.484 (3) | ||
O2—Pr1—O8 | 120.72 (6) | N9—Pr2—N8 | 66.25 (6) |
O2—Pr1—O4 | 67.39 (6) | N10—Pr2—N8 | 102.62 (6) |
O8—Pr1—O4 | 170.29 (6) | C1—O19—Pr2 | 124.79 (14) |
O2—Pr1—O7 | 131.93 (6) | C1—O19—H19 | 110 |
O8—Pr1—O7 | 49.83 (6) | Pr2—O19—H19 | 126 |
O4—Pr1—O7 | 121.21 (6) | C5—O20—Pr2 | 128.00 (15) |
O2—Pr1—O5 | 110.71 (6) | C5—O20—H20 | 111 |
O8—Pr1—O5 | 120.86 (5) | Pr2—O20—H20 | 119 |
O4—Pr1—O5 | 49.43 (5) | C10—O21—Pr2 | 126.65 (13) |
O7—Pr1—O5 | 74.87 (5) | C10—O21—H21 | 113 |
O2—Pr1—O11 | 102.45 (6) | Pr2—O21—H21 | 120 |
O8—Pr1—O11 | 64.38 (6) | C16—O22—Pr2 | 128.17 (14) |
O4—Pr1—O11 | 120.93 (6) | C16—O22—H22 | 106 |
O7—Pr1—O11 | 108.29 (6) | Pr2—O22—H22 | 124 |
O5—Pr1—O11 | 130.76 (6) | Pr2—O23—H23A | 129 |
O2—Pr1—O17 | 74.35 (6) | Pr2—O23—H23B | 131 |
O8—Pr1—O17 | 105.07 (6) | H23A—O23—H23B | 99 |
O4—Pr1—O17 | 70.97 (6) | C3—N7—C2 | 109.97 (19) |
O7—Pr1—O17 | 66.86 (6) | C3—N7—C14 | 109.50 (19) |
O5—Pr1—O17 | 61.97 (5) | C2—N7—C14 | 109.80 (19) |
O11—Pr1—O17 | 165.97 (5) | C3—N7—Pr2 | 112.18 (14) |
O2—Pr1—O1 | 49.33 (6) | C2—N7—Pr2 | 103.80 (14) |
O8—Pr1—O1 | 74.84 (6) | C14—N7—Pr2 | 111.46 (14) |
O4—Pr1—O1 | 114.47 (6) | C7—N8—C6 | 109.52 (19) |
O7—Pr1—O1 | 113.30 (6) | C7—N8—C4 | 108.6 (2) |
O5—Pr1—O1 | 159.38 (6) | C6—N8—C4 | 109.77 (19) |
O11—Pr1—O1 | 66.42 (6) | C7—N8—Pr2 | 111.37 (14) |
O17—Pr1—O1 | 102.69 (5) | C6—N8—Pr2 | 105.19 (14) |
O2—Pr1—O14 | 163.57 (6) | C4—N8—Pr2 | 112.32 (14) |
O8—Pr1—O14 | 71.18 (6) | C8—N9—C11 | 109.19 (18) |
O4—Pr1—O14 | 102.11 (6) | C8—N9—C9 | 108.03 (19) |
O7—Pr1—O14 | 64.04 (6) | C11—N9—C9 | 109.43 (18) |
O5—Pr1—O14 | 66.47 (6) | C8—N9—Pr2 | 112.87 (14) |
O11—Pr1—O14 | 71.41 (6) | C11—N9—Pr2 | 110.16 (14) |
O17—Pr1—O14 | 115.25 (5) | C9—N9—Pr2 | 107.08 (14) |
O1—Pr1—O14 | 134.08 (6) | C15—N10—C12 | 108.97 (19) |
O2—Pr1—O10 | 65.40 (6) | C15—N10—C13 | 109.86 (19) |
O8—Pr1—O10 | 109.86 (6) | C12—N10—C13 | 109.71 (19) |
O4—Pr1—O10 | 77.92 (6) | C15—N10—Pr2 | 106.87 (13) |
O7—Pr1—O10 | 156.60 (6) | C12—N10—Pr2 | 111.50 (14) |
O5—Pr1—O10 | 116.91 (5) | C13—N10—Pr2 | 109.88 (14) |
O11—Pr1—O10 | 48.41 (5) | O19—C1—C2 | 107.8 (2) |
O17—Pr1—O10 | 136.14 (5) | O19—C1—H1A | 110.1 |
O1—Pr1—O10 | 63.31 (6) | C2—C1—H1A | 110.1 |
O14—Pr1—O10 | 100.75 (6) | O19—C1—H1B | 110.1 |
O2—Pr1—O16 | 67.59 (6) | C2—C1—H1B | 110.1 |
O8—Pr1—O16 | 70.21 (6) | H1A—C1—H1B | 108.5 |
O4—Pr1—O16 | 110.90 (6) | N7—C2—C1 | 112.1 (2) |
O7—Pr1—O16 | 65.60 (6) | N7—C2—H2A | 109.2 |
O5—Pr1—O16 | 108.12 (5) | C1—C2—H2A | 109.2 |
O11—Pr1—O16 | 117.89 (6) | N7—C2—H2B | 109.2 |
O17—Pr1—O16 | 48.12 (5) | C1—C2—H2B | 109.2 |
O1—Pr1—O16 | 62.40 (6) | H2A—C2—H2B | 107.9 |
O14—Pr1—O16 | 128.84 (5) | N7—C3—C4 | 112.3 (2) |
O10—Pr1—O16 | 123.22 (5) | N7—C3—H3A | 109.1 |
O2—Pr1—O13 | 116.46 (6) | C4—C3—H3A | 109.1 |
O8—Pr1—O13 | 109.66 (5) | N7—C3—H3B | 109.1 |
O4—Pr1—O13 | 68.14 (6) | C4—C3—H3B | 109.1 |
O7—Pr1—O13 | 109.44 (5) | H3A—C3—H3B | 107.9 |
O5—Pr1—O13 | 66.50 (5) | N8—C4—C3 | 112.7 (2) |
O11—Pr1—O13 | 66.46 (6) | N8—C4—H4A | 109.0 |
O17—Pr1—O13 | 127.38 (5) | C3—C4—H4A | 109.0 |
O1—Pr1—O13 | 123.63 (5) | N8—C4—H4B | 109.0 |
O14—Pr1—O13 | 47.15 (5) | C3—C4—H4B | 109.0 |
O10—Pr1—O13 | 62.75 (5) | H4A—C4—H4B | 107.8 |
O16—Pr1—O13 | 173.92 (5) | O20—C5—C6 | 107.4 (2) |
N1—O1—Pr1 | 94.55 (14) | O20—C5—H5A | 110.2 |
N1—O2—Pr1 | 98.22 (14) | C6—C5—H5A | 110.2 |
N2—O4—Pr1 | 97.99 (13) | O20—C5—H5B | 110.2 |
N2—O5—Pr1 | 96.38 (13) | C6—C5—H5B | 110.2 |
N3—O7—Pr1 | 96.30 (13) | H5A—C5—H5B | 108.5 |
N3—O8—Pr1 | 96.72 (14) | N8—C6—C5 | 111.9 (2) |
N4—O10—Pr1 | 95.97 (13) | N8—C6—H6A | 109.2 |
N4—O11—Pr1 | 97.91 (13) | C5—C6—H6A | 109.2 |
N5—O13—Pr1 | 94.82 (13) | N8—C6—H6B | 109.2 |
N5—O14—Pr1 | 100.92 (14) | C5—C6—H6B | 109.2 |
N6—O16—Pr1 | 96.40 (13) | H6A—C6—H6B | 107.9 |
N6—O17—Pr1 | 97.92 (13) | N8—C7—C8 | 111.9 (2) |
O3—N1—O1 | 121.6 (2) | N8—C7—H7A | 109.2 |
O3—N1—O2 | 120.5 (2) | C8—C7—H7A | 109.2 |
O1—N1—O2 | 117.9 (2) | N8—C7—H7B | 109.2 |
O3—N1—Pr1 | 176.7 (2) | C8—C7—H7B | 109.2 |
O1—N1—Pr1 | 60.73 (12) | H7A—C7—H7B | 107.9 |
O2—N1—Pr1 | 57.17 (12) | N9—C8—C7 | 112.5 (2) |
O6—N2—O4 | 122.8 (2) | N9—C8—H8A | 109.1 |
O6—N2—O5 | 121.1 (2) | C7—C8—H8A | 109.1 |
O4—N2—O5 | 116.1 (2) | N9—C8—H8B | 109.1 |
O6—N2—Pr1 | 176.67 (19) | C7—C8—H8B | 109.1 |
O4—N2—Pr1 | 57.52 (12) | H8A—C8—H8B | 107.8 |
O5—N2—Pr1 | 58.65 (11) | N9—C9—C10 | 112.1 (2) |
O9—N3—O7 | 121.4 (2) | N9—C9—H9A | 109.2 |
O9—N3—O8 | 121.4 (2) | C10—C9—H9A | 109.2 |
O7—N3—O8 | 117.2 (2) | N9—C9—H9B | 109.2 |
O9—N3—Pr1 | 179.63 (19) | C10—C9—H9B | 109.2 |
O7—N3—Pr1 | 58.84 (11) | H9A—C9—H9B | 107.9 |
O8—N3—Pr1 | 58.31 (11) | O21—C10—C9 | 107.51 (19) |
O12—N4—O10 | 122.5 (2) | O21—C10—H10A | 110.2 |
O12—N4—O11 | 120.7 (2) | C9—C10—H10A | 110.2 |
O10—N4—O11 | 116.8 (2) | O21—C10—H10B | 110.2 |
O15—N5—O14 | 122.1 (2) | C9—C10—H10B | 110.2 |
O15—N5—O13 | 120.8 (2) | H10A—C10—H10B | 108.5 |
O14—N5—O13 | 117.0 (2) | N9—C11—C12 | 111.83 (19) |
O18—N6—O16 | 122.7 (2) | N9—C11—H11A | 109.2 |
O18—N6—O17 | 120.9 (2) | C12—C11—H11A | 109.2 |
O16—N6—O17 | 116.43 (19) | N9—C11—H11B | 109.2 |
O20—Pr2—O22 | 137.74 (6) | C12—C11—H11B | 109.2 |
O20—Pr2—O19 | 81.71 (6) | H11A—C11—H11B | 107.9 |
O22—Pr2—O19 | 86.19 (6) | N10—C12—C11 | 112.48 (19) |
O20—Pr2—O21 | 79.83 (6) | N10—C12—H12A | 109.1 |
O22—Pr2—O21 | 83.60 (6) | C11—C12—H12A | 109.1 |
O19—Pr2—O21 | 139.20 (6) | N10—C12—H12B | 109.1 |
O20—Pr2—O23 | 69.37 (7) | C11—C12—H12B | 109.1 |
O22—Pr2—O23 | 68.40 (6) | H12A—C12—H12B | 107.8 |
O19—Pr2—O23 | 70.94 (6) | N10—C13—C14 | 112.1 (2) |
O21—Pr2—O23 | 68.55 (6) | N10—C13—H13A | 109.2 |
O20—Pr2—N7 | 118.58 (6) | C14—C13—H13A | 109.2 |
O22—Pr2—N7 | 90.29 (6) | N10—C13—H13B | 109.2 |
O19—Pr2—N7 | 62.64 (6) | C14—C13—H13B | 109.2 |
O21—Pr2—N7 | 156.27 (6) | H13A—C13—H13B | 107.9 |
O23—Pr2—N7 | 129.98 (6) | N7—C14—C13 | 113.0 (2) |
O20—Pr2—N9 | 87.24 (6) | N7—C14—H14A | 109.0 |
O22—Pr2—N9 | 118.26 (6) | C13—C14—H14A | 109.0 |
O19—Pr2—N9 | 152.20 (6) | N7—C14—H14B | 109.0 |
O21—Pr2—N9 | 62.09 (6) | C13—C14—H14B | 109.0 |
O23—Pr2—N9 | 128.27 (6) | H14A—C14—H14B | 107.8 |
N7—Pr2—N9 | 101.75 (6) | N10—C15—C16 | 112.6 (2) |
O20—Pr2—N10 | 154.29 (6) | N10—C15—H15A | 109.1 |
O22—Pr2—N10 | 62.69 (6) | C16—C15—H15A | 109.1 |
O19—Pr2—N10 | 120.03 (6) | N10—C15—H15B | 109.1 |
O21—Pr2—N10 | 89.52 (6) | C16—C15—H15B | 109.1 |
O23—Pr2—N10 | 128.15 (6) | H15A—C15—H15B | 107.8 |
N7—Pr2—N10 | 67.43 (6) | O22—C16—C15 | 107.2 (2) |
N9—Pr2—N10 | 67.14 (6) | O22—C16—H16A | 110.3 |
O20—Pr2—N8 | 62.76 (6) | C15—C16—H16A | 110.3 |
O22—Pr2—N8 | 156.28 (6) | O22—C16—H16B | 110.3 |
O19—Pr2—N8 | 86.05 (6) | C15—C16—H16B | 110.3 |
O21—Pr2—N8 | 116.28 (6) | H16A—C16—H16B | 108.5 |
O23—Pr2—N8 | 129.22 (6) | H1WA—O1W—H1WB | 105 |
N7—Pr2—N8 | 66.27 (6) | H2WA—O2W—H2WB | 114 |
D—H···A | D—H | H···A | D···A | D—H···A |
O23—H23A···O13i | 0.84 (2) | 2.24 (2) | 2.979 (3) | 146 (2) |
O20—H20···O1W | 0.84 (2) | 1.79 (2) | 2.622 (3) | 174 (2) |
O23—H23B···O17 | 0.84 (2) | 2.02 (2) | 2.835 (3) | 164 (2) |
O1W—H1WA···O15i | 0.84 (2) | 2.05 (2) | 2.873 (3) | 165 (2) |
O1W—H1WB···O11ii | 0.84 (2) | 2.02 (2) | 2.849 (3) | 171 (2) |
O22—H22···O2W | 0.84 (2) | 1.78 (3) | 2.599 (3) | 166 (2) |
O21—H21···O13i | 0.84 (2) | 1.93 (2) | 2.768 (2) | 174 (2) |
O19—H19···O5 | 0.84 (2) | 1.87 (2) | 2.702 (2) | 169 (2) |
O2W—H2WA···O3iii | 0.84 (2) | 2.24 (2) | 3.079 (4) | 175 (2) |
O2W—H2WB···O9 | 0.84 (2) | 2.43 (2) | 3.032 (3) | 130 (2) |
O2W—H2WB···O7 | 0.84 (2) | 2.46 (2) | 3.078 (3) | 131 (2) |
O2W—H2WB···O6i | 0.84 (2) | 2.50 (2) | 3.191 (3) | 141 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Pr(C16H36N4O4)(H2O)][Pr(NO3)6]·2H2O |
Mr | 1056.42 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 15.5786 (3), 14.4453 (3), 15.5995 (3) |
β (°) | 99.749 (1) |
V (Å3) | 3459.78 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.89 |
Crystal size (mm) | 0.25 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.516, 0.651 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27454, 7950, 7143 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.654 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.023, 0.055, 1.09 |
No. of reflections | 7950 |
No. of parameters | 519 |
No. of restraints | 10 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.29, −0.73 |
Computer programs: COLLECT (Nonius, 1997-2002), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 2001), SHELXTL.
Pr1—O2 | 2.5568 (18) | Pr1—O13 | 2.7478 (17) |
Pr1—O8 | 2.5628 (18) | Pr2—O20 | 2.4548 (18) |
Pr1—O4 | 2.5687 (18) | Pr2—O22 | 2.4573 (18) |
Pr1—O7 | 2.5751 (17) | Pr2—O19 | 2.4698 (17) |
Pr1—O5 | 2.5910 (17) | Pr2—O21 | 2.4853 (17) |
Pr1—O11 | 2.6093 (18) | Pr2—O23 | 2.5596 (18) |
Pr1—O17 | 2.6287 (17) | Pr2—N7 | 2.677 (2) |
Pr1—O1 | 2.6354 (18) | Pr2—N9 | 2.682 (2) |
Pr1—O14 | 2.6445 (18) | Pr2—N10 | 2.7224 (19) |
Pr1—O10 | 2.6620 (18) | Pr2—N8 | 2.745 (2) |
Pr1—O16 | 2.6730 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O23—H23A···O13i | 0.84 (2) | 2.24 (2) | 2.979 (3) | 146 (2) |
O20—H20···O1W | 0.84 (2) | 1.79 (2) | 2.622 (3) | 174 (2) |
O23—H23B···O17 | 0.84 (2) | 2.02 (2) | 2.835 (3) | 164 (2) |
O1W—H1WA···O15i | 0.84 (2) | 2.05 (2) | 2.873 (3) | 165 (2) |
O1W—H1WB···O11ii | 0.84 (2) | 2.02 (2) | 2.849 (3) | 171 (2) |
O22—H22···O2W | 0.84 (2) | 1.78 (3) | 2.599 (3) | 166 (2) |
O21—H21···O13i | 0.84 (2) | 1.93 (2) | 2.768 (2) | 174 (2) |
O19—H19···O5 | 0.84 (2) | 1.87 (2) | 2.702 (2) | 169 (2) |
O2W—H2WA···O3iii | 0.84 (2) | 2.24 (2) | 3.079 (4) | 175 (2) |
O2W—H2WB···O9 | 0.84 (2) | 2.43 (2) | 3.032 (3) | 130 (2) |
O2W—H2WB···O7 | 0.84 (2) | 2.46 (2) | 3.078 (3) | 131 (2) |
O2W—H2WB···O6i | 0.84 (2) | 2.50 (2) | 3.191 (3) | 141 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1/2, −y+1/2, z+1/2. |
The title compound, (I), was obtained from the templated oligomerization of 1-azirideneethanol. The reaction was carried out under basic conditions which also yielded insoluble hydroxides. Slow evaporation of the filtrate gave needle-like crystals. The Pr3+ ions are in two distinct environments (see Fig. 1). In the first case, Pr1 is coordinated to six bidentate nitrate ions, resulting in an icosahedral polyhedron with Pr3+ ions having a coordination number (CN) of 12. In the second case, Pr2 is encapsulated in the macrocycle N,N',N'',N'''-tetrakis(2-hydroxyethyl)-1,4,7,10-tetrazacyclododecane (H4L), bonding to four tertiary amines and four alkoxides. The s tereochemistry of the chelate H4L is Δ(δδδδ). Atom Pr2 achieves a CN of 9 by bonding to a water molecule. The crystal structure is linked by O—H···O hydrogen bonds involving water molecules and the alkoxide groups (see Table 2 and Fig. 2). The crystal structure of (I) is the same as that found previously for the La analogue (Thompson, 2001).