Bis{N-[bis­(pyrrolidin-1-yl)phosphor­yl]-2,2,2-trichloro­acetamide}di­nitrato­dioxidouranium(VI)

Znovjyak, K.O.; Ovchynnikov, V.A.; Moroz, O.V.; Shishkina, S.V.; Amirkhanov, V.M.

doi:10.1107/S1600536810006422

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m322

doi:10.1107/S1600536810006422

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Bis{N-[bis(pyrrolidin-1-yl)phosphoryl]-2,2,2-trichloroacetamide}dinitratodioxidouranium(VI)

Kateryna O. Znovjyak,^a ^* Vladimir A. Ovchynnikov,^a Olesia V. Moroz,^a Svitlana V. Shishkina ^b and Vladimir M. Amirkhanov ^a

^aKyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine, and ^bSTC "Institute for Single Crystals", National Academy of Science of Ukraine, Lenina ave. 60, 61001, Khar'kov, Ukraine
^*Correspondence e-mail: znovkat@yahoo.com

(Received 11 February 2010; accepted 18 February 2010; online 24 February 2010)

The crystal structure of the title compound, [U(NO₃)₂O₂(C₁₀H₁₇Cl₃N₃O₂P)₂], is composed of centrosymmetric [UO₂(L)₂(NO₃)₂] molecules {L is N-[bis(pyrrolidin-1-yl)phosphoryl]-2,2,2-trichloroacetamide, C₁₀H₁₇Cl₃N₃O₂P}. The U^VI ion, located on an inversion center, is eight-coordinated with axial oxido ligands and six equatorial oxygen atoms of the phosphoryl and nitrate groups in a slightly distorted hexagonal-bipyramidal geometry. One of the pyrrolidine fragments in the ligand is disordered over two conformation (occupancy ratio 0.58:0.42). Intramolecular N—H⋯O hydrogen bonds between the amine and nitrate groups are found.

Related literature

For the synthesis and coordination properties of the ligand L, see: Znovjyak et al. (2009 ). For a structural investigation of L, see: Gholivand et al. (2006 ). For the synthesis and structural investigation of a uranium(IV)-containing complex with a similar ligand, see: Amirkhanov et al. (1997 ).

Experimental

Crystal data

[U(NO₃)₂O₂(C₁₀H₁₇Cl₃N₃O₂P)₂]
M_r = 1091.22
Triclinic, $[P \overline 1]$
a = 9.8292 (7) Å
b = 10.3436 (8) Å
c = 10.4475 (6) Å
α = 71.905 (6)°
β = 84.391 (5)°
γ = 71.475 (6)°
V = 957.34 (11) Å³
Z = 1
Mo Kα radiation
μ = 4.80 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.250, T_max = 0.447
22849 measured reflections
5523 independent reflections
5486 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.085
S = 0.98
5523 reflections
260 parameters
56 restraints
H-atom parameters constrained
Δρ_max = 1.93 e Å⁻³
Δρ_min = −1.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5	0.86	2.13	2.877 (4)	145

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810006422/dn2539sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006422/dn2539Isup2.hkl

checkCIF report

Comment top

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)₂and 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 (N_pyr)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°.

Related literature top

For the synthesis and coordination properties of the ligand L, see: Znovjyak et al. (2009). For a structural investigation of L, see: Gholivand et al. (2006). For the synthesis and structural investigation of a uranium(IV)-containing complex with a similar ligand, see: Amirkhanov et al. (1997).

Experimental top

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).

Computing details top

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).

Figures top

Fig. 1. View of the centrosymmetric molecule of 1 with atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. Hydrogen atoms not involved in hydrogen bonding omitted for clarity. [Symmetry code: (i) -x+1, -y+1, -z+1]

Bis{N-[bis(pyrrolidin-1-yl)phosphoryl]-2,2,2- trichloroacetamide}dinitratodioxidouranium(VI) top

Crystal data top

[U(NO₃)₂O₂(C₁₀H₁₇Cl₃N₃O₂P)₂]	Z = 1
M_r = 1091.22	F(000) = 530
Triclinic, P1	D_x = 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

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	5523 independent reflections
Radiation source: fine-focus sealed tube	5486 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
Detector resolution: 16.1827 pixels mm^-1	θ_max = 30.0°, θ_min = 3.0°
ω–scans	h = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −14→14
T_min = 0.250, T_max = 0.447	l = −14→14
22849 measured reflections

Refinement top

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(F_o²) + (0.0645P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
5523 reflections	Δρ_max = 1.93 e Å⁻³
260 parameters	Δρ_min = −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)

Crystal data top

[U(NO₃)₂O₂(C₁₀H₁₇Cl₃N₃O₂P)₂]	γ = 71.475 (6)°
M_r = 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)°

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	5523 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	5486 reflections with I > 2σ(I)
T_min = 0.250, T_max = 0.447	R_int = 0.090
22849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	56 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 0.98	Δρ_max = 1.93 e Å⁻³
5523 reflections	Δρ_min = −1.68 e Å⁻³
260 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.86	2.13	2.877 (4)	145

Experimental details

Crystal data
Chemical formula	[U(NO₃)₂O₂(C₁₀H₁₇Cl₃N₃O₂P)₂]
M_r	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)
T_min, T_max	0.250, 0.447
No. of measured, independent and observed [I > 2σ(I)] reflections	22849, 5523, 5486
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.86	2.13	2.877 (4)	145.0

References

Amirkhanov, V., Sieler, J., Trush, V., Ovchynnikov, V. & Domasevitch, K. (1997). Z. Naturforsch. Teil B, 52, 1194–1198. CAS Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEP-III. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gholivand, K., Alizadehgan, A., Arshadi, S. & Firooz, A. (2006). J. Mol. Struct. 791, 193–200. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Znovjyak, K., Moroz, O., Ovchynnikov, V., Sliva, T., Shishkina, S. & Amirkhanov, V. (2009). Polyhedron, 28, 3731–3738. Web of Science CSD CrossRef CAS Google Scholar

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Volume 66| Part 3| March 2010| Page m322

doi:10.1107/S1600536810006422

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis{N-[bis­­(pyrrolidin-1-yl)phosphor­yl]-2,2,2-tri­chloro­acetamide}di­nitrato­dioxidouranium(VI)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Bis{N-[bis(pyrrolidin-1-yl)phosphoryl]-2,2,2-trichloroacetamide}dinitratodioxidouranium(VI)