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

Abstract

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,

• 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) ų

• 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 ▶) 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[F ² > 2σ(F ²)] = 0.034

• wR(F ²) = 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

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

supplementary crystallographic information

Comment

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 (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°.

Experimental

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).

Refinement

All H atoms were placed at calculated positions and treated as riding on their parent atoms [C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C), N—H = 0.86 Å and U_iso(H) = 1.2U_eq(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.

Figures

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]

Crystal data

[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

Data collection

Oxford Diffraction Xcalibur3 diffractometer	5523 independent reflections
Radiation source: fine-focus sealed tube	5486 reflections with I > 2σ(I)
graphite	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

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)

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	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, °)

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 codes: (i) −x+1, −y+1, −z+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