Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810006422/dn2539sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536810006422/dn2539Isup2.hkl |
CCDC reference: 769900
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- Disorder in main residue
- R factor = 0.034
- wR factor = 0.085
- Data-to-parameter ratio = 21.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C9
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for U PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 10 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 7 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 43 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 14
Alert level G PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 14.00 Perc. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 56 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 16 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 1.00 Deg. C6B -N2 -C6A 1.555 1.555 1.555 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 6.40 Deg. C3B -N2 -C3A 1.555 1.555 1.555 PLAT793_ALERT_4_G The Model has Chirality at P1 (Verify) .... S PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... !
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 9 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The synthesis of L was carried out according to the procedure described previously (Znovjyak et al., 2009).
Hydrated nitrate UO2(NO3)22H2O (1 mmol) was solved upon heating in a CH3CN (10 ml). The solution was dehydrated by HC(OC2H5)3 (2 mmol), then heated to the boiling point and cooled down. The resulting solution was added to the solution of L (2 mmol) in CH3OH (10 ml) and was left in a vacuum desiccator over CaCl2 at room temperature. After 1 day, the yellow crystals were filtered off and washed with cold isopropanol and dried on the air (yield 80%). IR (KBr, cm-1): 3280 ν(NH), 2990 ν(CH), 2890 ν(CH), 1730 ν(CO), 1530, 1440 ν(CN), 1380, 1275, 1215, 1145 ν(PO), 1085, 1030, 940, 890, 820, 680 ν(CCl).
All H atoms were placed at calculated positions and treated as riding on their parent atoms [C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C), N—H = 0.86 Å and Uiso(H) = 1.2Ueq(N)]. In one pyrrolidine group, atoms C3—C6 were treated as disordered between two orientations A and B, respectively, with the occupancies to 0.58 and 0.42.
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Burnett & Johnson, 1996; Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[U(NO3)2O2(C10H17Cl3N3O2P)2] | Z = 1 |
Mr = 1091.22 | F(000) = 530 |
Triclinic, P1 | Dx = 1.893 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8292 (7) Å | Cell parameters from 35271 reflections |
b = 10.3436 (8) Å | θ = 3.0–40.8° |
c = 10.4475 (6) Å | µ = 4.80 mm−1 |
α = 71.905 (6)° | T = 293 K |
β = 84.391 (5)° | Block, yellow |
γ = 71.475 (6)° | 0.40 × 0.30 × 0.20 mm |
V = 957.34 (11) Å3 |
Oxford Diffraction Xcalibur3 diffractometer | 5523 independent reflections |
Radiation source: fine-focus sealed tube | 5486 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.090 |
Detector resolution: 16.1827 pixels mm-1 | θmax = 30.0°, θmin = 3.0° |
ω–scans | h = −13→13 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −14→14 |
Tmin = 0.250, Tmax = 0.447 | l = −14→14 |
22849 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)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0645P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
5523 reflections | Δρmax = 1.93 e Å−3 |
260 parameters | Δρmin = −1.68 e Å−3 |
56 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0164 (15) |
[U(NO3)2O2(C10H17Cl3N3O2P)2] | γ = 71.475 (6)° |
Mr = 1091.22 | V = 957.34 (11) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.8292 (7) Å | Mo Kα radiation |
b = 10.3436 (8) Å | µ = 4.80 mm−1 |
c = 10.4475 (6) Å | T = 293 K |
α = 71.905 (6)° | 0.40 × 0.30 × 0.20 mm |
β = 84.391 (5)° |
Oxford Diffraction Xcalibur3 diffractometer | 5523 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 5486 reflections with I > 2σ(I) |
Tmin = 0.250, Tmax = 0.447 | Rint = 0.090 |
22849 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 56 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 0.98 | Δρmax = 1.93 e Å−3 |
5523 reflections | Δρmin = −1.68 e Å−3 |
260 parameters |
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. 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 | Occ. (<1) | |
U | 0.5000 | 0.5000 | 0.5000 | 0.03209 (7) | |
Cl1 | 1.08718 (12) | 0.15464 (16) | 0.42224 (11) | 0.0674 (3) | |
Cl2 | 1.27581 (13) | −0.08470 (15) | 0.60993 (14) | 0.0711 (3) | |
Cl3 | 1.23459 (15) | 0.1967 (2) | 0.6270 (2) | 0.0834 (4) | |
P1 | 0.74992 (8) | 0.19775 (8) | 0.75384 (8) | 0.03262 (14) | |
O1 | 0.6348 (3) | 0.2904 (3) | 0.6531 (3) | 0.0474 (6) | |
O2 | 1.0554 (3) | −0.0118 (4) | 0.8039 (3) | 0.0613 (9) | |
O3 | 0.5489 (3) | 0.6026 (4) | 0.5826 (3) | 0.0526 (6) | |
O4 | 0.6361 (3) | 0.5934 (3) | 0.2862 (3) | 0.0520 (7) | |
O5 | 0.7579 (3) | 0.4078 (4) | 0.4326 (3) | 0.0588 (8) | |
O6 | 0.8601 (4) | 0.4932 (4) | 0.2460 (4) | 0.0688 (10) | |
N1 | 0.8984 (3) | 0.1713 (3) | 0.6561 (3) | 0.0373 (5) | |
H1 | 0.8905 | 0.2245 | 0.5738 | 0.045* | |
N3 | 0.7074 (3) | 0.0571 (3) | 0.8365 (3) | 0.0420 (6) | |
N4 | 0.7559 (3) | 0.4981 (4) | 0.3181 (3) | 0.0432 (6) | |
C1 | 1.0286 (3) | 0.0743 (4) | 0.6952 (3) | 0.0383 (6) | |
C2 | 1.1511 (4) | 0.0847 (4) | 0.5899 (4) | 0.0445 (7) | |
N2 | 0.7919 (3) | 0.2608 (4) | 0.8625 (4) | 0.0450 (6) | |
C3A | 0.6874 (16) | 0.2992 (18) | 0.9673 (15) | 0.056 (4) | 0.58 |
H3A1 | 0.7145 | 0.2300 | 1.0549 | 0.067* | 0.58 |
H3A2 | 0.5915 | 0.3050 | 0.9453 | 0.067* | 0.58 |
C4A | 0.6950 (10) | 0.4427 (12) | 0.9649 (15) | 0.072 (3) | 0.58 |
H4A1 | 0.6628 | 0.4628 | 1.0494 | 0.086* | 0.58 |
H4A2 | 0.6384 | 0.5183 | 0.8917 | 0.086* | 0.58 |
C5A | 0.8571 (12) | 0.4237 (17) | 0.9427 (18) | 0.084 (4) | 0.58 |
H5A1 | 0.8771 | 0.5144 | 0.9155 | 0.101* | 0.58 |
H5A2 | 0.9129 | 0.3609 | 1.0223 | 0.101* | 0.58 |
C6A | 0.884 (2) | 0.355 (2) | 0.828 (2) | 0.066 (6) | 0.58 |
H6A1 | 0.8564 | 0.4270 | 0.7415 | 0.079* | 0.58 |
H6A2 | 0.9840 | 0.3007 | 0.8241 | 0.079* | 0.58 |
C3B | 0.692 (3) | 0.282 (3) | 0.974 (2) | 0.075 (7) | 0.42 |
H3B1 | 0.5935 | 0.3271 | 0.9419 | 0.090* | 0.42 |
H3B2 | 0.6979 | 0.1919 | 1.0426 | 0.090* | 0.42 |
C4B | 0.743 (2) | 0.377 (2) | 1.0253 (19) | 0.096 (5) | 0.42 |
H4B1 | 0.8132 | 0.3208 | 1.0961 | 0.115* | 0.42 |
H4B2 | 0.6634 | 0.4393 | 1.0611 | 0.115* | 0.42 |
C5B | 0.810 (3) | 0.4639 (19) | 0.904 (3) | 0.096 (6) | 0.42 |
H5B1 | 0.7379 | 0.5434 | 0.8473 | 0.116* | 0.42 |
H5B2 | 0.8789 | 0.4995 | 0.9322 | 0.116* | 0.42 |
C6B | 0.885 (3) | 0.352 (3) | 0.831 (3) | 0.072 (8) | 0.42 |
H6B1 | 0.8895 | 0.3961 | 0.7349 | 0.086* | 0.42 |
H6B2 | 0.9811 | 0.2988 | 0.8655 | 0.086* | 0.42 |
C7 | 0.6093 (4) | 0.0065 (5) | 0.7792 (4) | 0.0497 (8) | |
H7A | 0.6362 | 0.0058 | 0.6875 | 0.060* | |
H7B | 0.5109 | 0.0666 | 0.7797 | 0.060* | |
C8 | 0.6270 (8) | −0.1427 (7) | 0.8705 (8) | 0.0852 (18) | |
H8A | 0.5426 | −0.1457 | 0.9265 | 0.102* | |
H8B | 0.6408 | −0.2085 | 0.8180 | 0.102* | |
C9 | 0.7537 (12) | −0.1812 (7) | 0.9542 (8) | 0.109 (3) | |
H9A | 0.8378 | −0.2340 | 0.9145 | 0.131* | |
H9B | 0.7402 | −0.2411 | 1.0435 | 0.131* | |
C10 | 0.7735 (5) | −0.0494 (5) | 0.9627 (4) | 0.0582 (10) | |
H10A | 0.8744 | −0.0588 | 0.9669 | 0.070* | |
H10B | 0.7250 | −0.0240 | 1.0409 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
U | 0.02715 (9) | 0.02741 (9) | 0.03229 (10) | −0.00624 (5) | −0.00343 (5) | 0.00313 (5) |
Cl1 | 0.0505 (5) | 0.0857 (9) | 0.0435 (5) | −0.0017 (5) | 0.0060 (4) | −0.0091 (5) |
Cl2 | 0.0527 (6) | 0.0636 (7) | 0.0744 (7) | 0.0138 (5) | 0.0040 (5) | −0.0225 (6) |
Cl3 | 0.0579 (6) | 0.0868 (10) | 0.1247 (13) | −0.0366 (7) | 0.0060 (7) | −0.0446 (10) |
P1 | 0.0271 (3) | 0.0258 (3) | 0.0332 (3) | −0.0036 (2) | −0.0009 (2) | 0.0033 (3) |
O1 | 0.0287 (10) | 0.0412 (13) | 0.0442 (12) | 0.0003 (9) | −0.0008 (9) | 0.0152 (10) |
O2 | 0.0430 (14) | 0.067 (2) | 0.0440 (14) | 0.0099 (13) | −0.0099 (11) | 0.0004 (14) |
O3 | 0.0576 (16) | 0.0518 (17) | 0.0555 (16) | −0.0269 (13) | −0.0045 (12) | −0.0136 (13) |
O4 | 0.0400 (12) | 0.0461 (15) | 0.0446 (13) | −0.0036 (11) | 0.0033 (10) | 0.0110 (11) |
O5 | 0.0386 (13) | 0.0545 (18) | 0.0472 (14) | 0.0013 (11) | 0.0060 (11) | 0.0173 (12) |
O6 | 0.0469 (15) | 0.072 (2) | 0.0606 (18) | −0.0101 (15) | 0.0194 (14) | 0.0037 (16) |
N1 | 0.0283 (11) | 0.0379 (14) | 0.0335 (12) | −0.0001 (9) | −0.0020 (9) | −0.0032 (10) |
N3 | 0.0400 (13) | 0.0332 (14) | 0.0412 (14) | −0.0116 (11) | −0.0122 (11) | 0.0093 (11) |
N4 | 0.0355 (13) | 0.0411 (15) | 0.0393 (14) | −0.0073 (11) | 0.0042 (10) | 0.0016 (11) |
C1 | 0.0307 (13) | 0.0410 (17) | 0.0385 (14) | −0.0019 (11) | −0.0061 (11) | −0.0124 (13) |
C2 | 0.0318 (14) | 0.0473 (19) | 0.0478 (18) | −0.0044 (13) | −0.0006 (12) | −0.0124 (15) |
N2 | 0.0428 (14) | 0.0428 (16) | 0.0518 (16) | −0.0165 (12) | 0.0106 (12) | −0.0170 (14) |
C3A | 0.052 (6) | 0.067 (7) | 0.056 (6) | −0.023 (5) | 0.034 (6) | −0.035 (6) |
C4A | 0.049 (4) | 0.071 (6) | 0.106 (8) | −0.009 (4) | 0.013 (5) | −0.054 (6) |
C5A | 0.054 (5) | 0.094 (9) | 0.141 (11) | −0.028 (6) | 0.021 (6) | −0.087 (9) |
C6A | 0.055 (10) | 0.064 (10) | 0.107 (12) | −0.043 (8) | 0.032 (9) | −0.049 (9) |
C3B | 0.073 (13) | 0.066 (11) | 0.082 (14) | −0.011 (8) | −0.019 (9) | −0.024 (9) |
C4B | 0.112 (13) | 0.102 (13) | 0.096 (11) | −0.030 (10) | 0.004 (9) | −0.064 (10) |
C5B | 0.109 (16) | 0.059 (9) | 0.134 (14) | −0.019 (9) | 0.002 (11) | −0.055 (9) |
C6B | 0.055 (14) | 0.066 (15) | 0.100 (15) | −0.006 (10) | −0.007 (9) | −0.042 (12) |
C7 | 0.0418 (17) | 0.052 (2) | 0.054 (2) | −0.0214 (16) | −0.0004 (14) | −0.0055 (17) |
C8 | 0.089 (4) | 0.058 (3) | 0.110 (5) | −0.046 (3) | −0.009 (3) | 0.000 (3) |
C9 | 0.171 (8) | 0.042 (3) | 0.102 (5) | −0.043 (4) | −0.060 (5) | 0.024 (3) |
C10 | 0.059 (2) | 0.048 (2) | 0.0467 (19) | −0.0157 (18) | −0.0118 (16) | 0.0179 (16) |
U—O3 | 1.754 (3) | C4A—C5A | 1.546 (12) |
U—O3i | 1.754 (3) | C4A—H4A1 | 0.9700 |
U—O1 | 2.334 (2) | C4A—H4A2 | 0.9700 |
U—O1i | 2.334 (2) | C5A—C6A | 1.538 (13) |
U—O5 | 2.523 (3) | C5A—H5A1 | 0.9700 |
U—O5i | 2.523 (3) | C5A—H5A2 | 0.9700 |
U—O4i | 2.571 (3) | C6A—H6A1 | 0.9700 |
U—O4 | 2.571 (3) | C6A—H6A2 | 0.9700 |
Cl1—C2 | 1.768 (4) | C3B—C4B | 1.482 (16) |
Cl2—C2 | 1.753 (4) | C3B—H3B1 | 0.9700 |
Cl3—C2 | 1.764 (4) | C3B—H3B2 | 0.9700 |
P1—O1 | 1.491 (2) | C4B—C5B | 1.542 (18) |
P1—N3 | 1.604 (3) | C4B—H4B1 | 0.9700 |
P1—N2 | 1.615 (3) | C4B—H4B2 | 0.9700 |
P1—N1 | 1.696 (3) | C5B—C6B | 1.531 (15) |
O2—C1 | 1.197 (5) | C5B—H5B1 | 0.9700 |
O4—N4 | 1.267 (4) | C5B—H5B2 | 0.9700 |
O5—N4 | 1.265 (4) | C6B—H6B1 | 0.9700 |
O6—N4 | 1.208 (4) | C6B—H6B2 | 0.9700 |
N1—C1 | 1.357 (4) | C7—C8 | 1.507 (8) |
N1—H1 | 0.8600 | C7—H7A | 0.9700 |
N3—C10 | 1.478 (5) | C7—H7B | 0.9700 |
N3—C7 | 1.481 (5) | C8—C9 | 1.468 (10) |
C1—C2 | 1.556 (5) | C8—H8A | 0.9700 |
N2—C6B | 1.460 (14) | C8—H8B | 0.9700 |
N2—C6A | 1.475 (8) | C9—C10 | 1.467 (8) |
N2—C3B | 1.473 (14) | C9—H9A | 0.9700 |
N2—C3A | 1.484 (7) | C9—H9B | 0.9700 |
C3A—C4A | 1.502 (13) | C10—H10A | 0.9700 |
C3A—H3A1 | 0.9700 | C10—H10B | 0.9700 |
C3A—H3A2 | 0.9700 | ||
O3—U—O3i | 180.00 (13) | C4A—C3A—H3A2 | 111.1 |
O3—U—O1 | 90.47 (14) | H3A1—C3A—H3A2 | 109.0 |
O3i—U—O1 | 89.53 (14) | C3A—C4A—C5A | 101.7 (8) |
O3—U—O1i | 89.53 (14) | C3A—C4A—H4A1 | 111.4 |
O3i—U—O1i | 90.47 (14) | C5A—C4A—H4A1 | 111.4 |
O1—U—O1i | 180.0 | C3A—C4A—H4A2 | 111.4 |
O3—U—O5 | 90.00 (14) | C5A—C4A—H4A2 | 111.4 |
O3i—U—O5 | 90.00 (14) | H4A1—C4A—H4A2 | 109.3 |
O1—U—O5 | 65.33 (9) | C6A—C5A—C4A | 99.5 (10) |
O1i—U—O5 | 114.67 (9) | C6A—C5A—H5A1 | 111.9 |
O3—U—O5i | 90.00 (14) | C4A—C5A—H5A1 | 111.9 |
O3i—U—O5i | 90.00 (14) | C6A—C5A—H5A2 | 111.9 |
O1—U—O5i | 114.67 (9) | C4A—C5A—H5A2 | 111.9 |
O1i—U—O5i | 65.33 (9) | H5A1—C5A—H5A2 | 109.6 |
O5—U—O5i | 180.0 | N2—C6A—C5A | 103.7 (8) |
O3—U—O4i | 88.35 (13) | N2—C6A—H6A1 | 111.0 |
O3i—U—O4i | 91.65 (13) | C5A—C6A—H6A1 | 111.0 |
O1—U—O4i | 65.33 (8) | N2—C6A—H6A2 | 111.0 |
O1i—U—O4i | 114.67 (8) | C5A—C6A—H6A2 | 111.0 |
O5—U—O4i | 130.60 (9) | H6A1—C6A—H6A2 | 109.0 |
O5i—U—O4i | 49.40 (9) | C4B—C3B—N2 | 102.4 (11) |
O3—U—O4 | 91.65 (13) | C4B—C3B—H3B1 | 111.3 |
O3i—U—O4 | 88.35 (13) | N2—C3B—H3B1 | 111.3 |
O1—U—O4 | 114.67 (8) | C4B—C3B—H3B2 | 111.3 |
O1i—U—O4 | 65.33 (8) | N2—C3B—H3B2 | 111.3 |
O5—U—O4 | 49.40 (9) | H3B1—C3B—H3B2 | 109.2 |
O5i—U—O4 | 130.60 (9) | C3B—C4B—C5B | 105.9 (13) |
O4i—U—O4 | 180.0 | C3B—C4B—H4B1 | 110.6 |
O1—P1—N3 | 108.41 (16) | C5B—C4B—H4B1 | 110.6 |
O1—P1—N2 | 119.57 (19) | C3B—C4B—H4B2 | 110.6 |
N3—P1—N2 | 107.23 (17) | C5B—C4B—H4B2 | 110.6 |
O1—P1—N1 | 102.49 (14) | H4B1—C4B—H4B2 | 108.7 |
N3—P1—N1 | 115.72 (16) | C6B—C5B—C4B | 101.6 (13) |
N2—P1—N1 | 103.76 (15) | C6B—C5B—H5B1 | 111.5 |
P1—O1—U | 157.1 (2) | C4B—C5B—H5B1 | 111.5 |
N4—O4—U | 96.89 (19) | C6B—C5B—H5B2 | 111.5 |
N4—O5—U | 99.3 (2) | C4B—C5B—H5B2 | 111.5 |
C1—N1—P1 | 126.3 (2) | H5B1—C5B—H5B2 | 109.3 |
C1—N1—H1 | 116.9 | N2—C6B—C5B | 102.6 (11) |
P1—N1—H1 | 116.9 | N2—C6B—H6B1 | 111.2 |
C10—N3—C7 | 110.9 (3) | C5B—C6B—H6B1 | 111.2 |
C10—N3—P1 | 127.0 (3) | N2—C6B—H6B2 | 111.2 |
C7—N3—P1 | 121.4 (2) | C5B—C6B—H6B2 | 111.2 |
O6—N4—O5 | 122.5 (3) | H6B1—C6B—H6B2 | 109.2 |
O6—N4—O4 | 123.1 (3) | N3—C7—C8 | 104.1 (4) |
O5—N4—O4 | 114.4 (3) | N3—C7—H7A | 110.9 |
O2—C1—N1 | 125.1 (3) | C8—C7—H7A | 110.9 |
O2—C1—C2 | 119.3 (3) | N3—C7—H7B | 110.9 |
N1—C1—C2 | 115.5 (3) | C8—C7—H7B | 110.9 |
C1—C2—Cl2 | 109.9 (3) | H7A—C7—H7B | 108.9 |
C1—C2—Cl3 | 105.5 (2) | C9—C8—C7 | 106.4 (4) |
Cl2—C2—Cl3 | 109.3 (2) | C9—C8—H8A | 110.4 |
C1—C2—Cl1 | 112.6 (2) | C7—C8—H8A | 110.4 |
Cl2—C2—Cl1 | 108.7 (2) | C9—C8—H8B | 110.4 |
Cl3—C2—Cl1 | 110.8 (2) | C7—C8—H8B | 110.4 |
C6B—N2—C6A | 1 (2) | H8A—C8—H8B | 108.6 |
C6B—N2—C3B | 113.4 (9) | C8—C9—C10 | 108.4 (5) |
C6A—N2—C3B | 113.9 (9) | C8—C9—H9A | 110.0 |
C6B—N2—C3A | 109.0 (9) | C10—C9—H9A | 110.0 |
C6A—N2—C3A | 109.3 (6) | C8—C9—H9B | 110.0 |
C3B—N2—C3A | 6.4 (17) | C10—C9—H9B | 110.0 |
C6B—N2—P1 | 123.2 (10) | H9A—C9—H9B | 108.4 |
C6A—N2—P1 | 122.1 (7) | C9—C10—N3 | 103.0 (4) |
C3B—N2—P1 | 118.4 (8) | C9—C10—H10A | 111.2 |
C3A—N2—P1 | 120.3 (6) | N3—C10—H10A | 111.2 |
N2—C3A—C4A | 103.5 (7) | C9—C10—H10B | 111.2 |
N2—C3A—H3A1 | 111.1 | N3—C10—H10B | 111.2 |
C4A—C3A—H3A1 | 111.1 | H10A—C10—H10B | 109.1 |
N2—C3A—H3A2 | 111.1 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [U(NO3)2O2(C10H17Cl3N3O2P)2] |
Mr | 1091.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.8292 (7), 10.3436 (8), 10.4475 (6) |
α, β, γ (°) | 71.905 (6), 84.391 (5), 71.475 (6) |
V (Å3) | 957.34 (11) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 4.80 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur3 diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.250, 0.447 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22849, 5523, 5486 |
Rint | 0.090 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.085, 0.98 |
No. of reflections | 5523 |
No. of parameters | 260 |
No. of restraints | 56 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.93, −1.68 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Burnett & Johnson, 1996; Farrugia, 1997), WinGX (Farrugia, 1999).
As a part of our study of coordination compounds based on carbacylamidophosphates with C(O)NHP(O) structural fragment we obtained the title compound UO2(L)2(NO3)2 (L = 2,2,2-trichloro- N-[di(1-pyrrolidinyl)phosphoryl]acetamide) (1), and solved its crystal structure. It was shown previously that L is able to form complexes with lanthanides (Znovjyak et al., 2009).
The crystal structure of 1 is made of centrosymmetric molecules UO2(L)2(NO3)2 and uranium is located on an inversion center. The analysis of the bond lengths and angles of 1 indicates that the coordination polyhedra of the uranium ions are slightly distorted hexagonal bipyramids. The axial vertices are occupied by two oxido ligands while six oxygen atoms of monodentate coordinated L ligands and bidentate coordinated nitrate groups lie in the equatorial plane. The nitrate groups additionally form intramolecular hydrogen bonding with the hydrogen atoms of the N—H groups of the L ligands (Table 1). In the crystal structure of the complex, the phosphoryl and carbonyl groups are in the trans position to each other which was early observed in the structure of the free L (Gholivand et al., 2006) and similar complex with uranium ion (Amirkhanov et al., 1997). It was shown that 2,2,2-trichloro-N-[di(1-pyrrolidinyl)phosphoryl]acetamide aggregates into non-centrosymmetric dimers (L)2, therefore in the following will be given two values of bond lengths due to comparison of non-coordinated and coordinated L.
The planar four-membered metalocycle UONO is characterised by an average angle U—O—N equal to 98.1 °. Bond length U—O(oxido ligand) is equal to 1.754 (3) Å while U—O(NO3) and U—O(PO) are 2.523 (3)-2.573 (3) Å and 2.334 (3) Å, respectively. The O—N—O angle of the chelate ring (114.3 (3) °) are shorter as compared to other angles O—N—O (122.3 (4)-123.3 (4) °). N—O(non-coordinated) and N—O(coordinated) distances fall in the range of 1.204 (5) Å and 1.265 (4)-1.270 (5) Å, respectively. In the coordinated L ligand the P—O bond length is slightly increased upon coordination (1.492 (3) Å). In the case of the non-coordinated molecule L they are 1.479 Å and 1.469 Å. The P—N bond distances between phosphorus atoms and nitrogen atoms of the pyrrolidine substituents are shortened with respect to observed values in L (1.613 (4)-1.625 (4) Å) and fall in the range 1.605 (3)-1.613 (4) Å, that can be explained by increasing π-donor bonding in the (Npyr)2P(O) fragment due to coordination. In 1, the P—N(NH) bond length (1.695 (3) Å) is shortened as compared to (L)2 (1.697 and 1.707 Å). The C—N distance is increased while C—O distance do not change upon ligand coordination and are equal to 1.359 (4) Å and 1.196 (5) Å, respectively. Angles in the fragment C(O)NHP(O) are slightly changed upon coordination in the range of 2-3°.