Tetra­piperidinium di-μ-methoxy-di-μ₅-oxo-tetra-μ₃-oxo-dodeca-μ₂-oxo-octa­oxodeca­vanadate

The structure of the title compound, (C₅H₁₂N)₄[V₁₀O₂₆(CH₃O)₂], reveals the presence of four protonated piperidin­ium cations and a [{V₁₀O₂₆}(OCH₃)₂]⁴⁻ polyanion having an embedded centre of inversion. The compound is distinguished by presenting, in contrast with other anionic deca­vanadates, two meth­oxy groups bridging the outermost V atoms, and it becomes the first example of this type among reported deca­vanadates.

S1. Comment

Polyoxometallates have received increasing attention in recent years, since they have been used successfully as drugs with antiviral activity, for example against herpes or HIV (Rhule et al., 1998). In many other fields, such as catalysis, biology and materials science, the possible applications of polyoxometallates also attract much attention (Müller et al., 1998; Oyaizu & Tsuchida, 1998; Pope & Müller, 1991). In particular, the polyoxovanadate clusters, an important class of polyoxometallates, have been studied extensively because of their fascinating structure and potential applications (Zhang & Chen, 2003). Recently, some interesting studies have been carried out to investigate the interactions of polyoxovanadate with organic ligands (Khan et al., 1993, 1992). Taking into account the above facts, the synthesis of new polyoxovanadates is of considerable interest in order to gain insight into the nature of this kind of complex. In this paper, the title new decavanadate compound with the piperidinium cation, formulated as [(C₅H₁₂N)₄][V₁₀O₂₆(OCH₃)₂], (I), has been synthesized and characterized by single-crystal X-ray diffraction and the results are presented here.

Compound (I) contains a [V₁₀O₂₆(OCH₃)₂]⁴⁻ polyanion and four protonated piperidinium cations. As shown in Fig. 1, its structure consists of a centrosymmetric framework of ten V atoms disposed as two almost regular V₆ octahedra with a common edge, V5—V5ⁱ [symmetry code: (i) −x + 1, −y, −z + 1], the V···V distances ranging from 3.0169 (9) (V1—V5) to 3.2730 (12) Å (V5—V5ⁱ). Each V atom coordinates to six O atoms to form ten small VO₆ octahedra occupying the framework vertexes. The ten V atoms can be distinguished into three categories, namely V_a = atoms V5 and V5ⁱ, V_b = atoms V2, V4, V2ⁱ and V4ⁱ, and V_c = atoms V1, V3, V1ⁱ and V3ⁱ. V_a atoms form the common edge, as mentioned above, V_b atoms form two tetrahedra and V_c atoms form quadrangles with V_a atoms. In the polyanion, four different modes for bonding of the oxo ligands are present. Eight terminal O atoms, O1–O4 and O1ⁱ–O4ⁱ, are simply η¹-bonded to V_b and V_c atoms, with short V—O distances from 1.598 (2) (V2—O2) to 1.603 (2) Å (V4—O4), which indicate substantial V═O character (Table 1). Atoms O5, O5ⁱ, O7–O11 and O7ⁱ–O11ⁱ are µ₂-bonded to the corresponding V—V edges of the framework. Two short distances [V5—O5 = 1.689 (2) Å and V5—O9 = 1.684 (2) Å] are observed and result in the two long V—O distances V1—O9 [2.033 (2) Å] and V3ⁱ—O5 [2.033 (2) Å]. For other µ₂-bridging oxo ligands, the V—O distances are in the range 1.755 (2)–1.904 (2) Å (V2—O10 and V3—O10, respectively). Atoms O12, O13, O12ⁱ and O13ⁱ are µ₃-bridging O atoms which form similar V—O interactions in the range 1.903 (2)–2.051 (2) Å (V5—O13 and V2—O13). Finally, both atoms O14 and O14ⁱ are in the centre of a V₆ octahedron and coordinate to six V atoms with long V—O distances, ranging from 2.072 (2) (V5—O14) to 2.337 (2) Å (V3—O14), which obviously correlate with the short V—O distances discussed above.

An interesting feature of the structure of (I) is the geometry of the µ₂-bridging methoxyl ligands. This is the first example of such a group acting as a component of a decavanadium cluster, although it has previously been observed in some other vanadium complexes (Chen & Zubieta, 1993; Hitchcock et al., 1997; Hughes et al., 1994; Mikuriya et al., 1993; Jiang et al., 1998; Herron et al., 1997). The O atom of the methoxyl ligand (O6) is µ₂-bonded to atoms V1 and V2, with bond lengths of 1.952 (2) and 2.007 (2) Å, respectively, which are more similar to the distances between the V atoms and the µ₃-bridging oxo ligands than to the µ₂-bridging ones. The displacement of atom O6 from the V1/V2/C1 plane is 0.2507 (33) Å. The angles C1—O6—V1 and C1—O6—V2 are 122.0 (2) and 121.0 (2)°, respectively. These features imply that the µ₂-bridging atom O6 bonds to V1 and V2 with sp² hybrid orbitals.

In the crystal structure of (I), the six-membered piperidine rings occur in a chair conformation. The puckering parameters (Cremer & Pople, 1975) are σ = 2.8 (4)°, ϕ = 172 (9)° and Q = 0.551 (5) Å for the N1 ring, and σ = 6.1 (5)°, ϕ = −174 (5)° and Q = 0.553 (5) Å for the N2 ring. Each piperidinium cation interacts with two [V₁₀O₂₆(OCH₃)₂]⁴⁻ anions via N—H···O hydrogen bonds (Table 2), which results in a three-dimensional hydrogen-bonding structure, with the N2 H atoms joining decavanadate units along the (101) plane and the N1 oH atoms binding along the [100] direction (Fig. 2).

S2. Experimental

Although the initial scope of this work was to prepare a polynuclear complex of oxovanadium(IV) bridged by pyromellitic acid, during the synthetic process a pentavalent species was obtained. It was also found that the decavanadate was easily generated in the experimental pH conditions used, a fact already mentioned in some earlier references (Pope, 1983; Duraisamy et al., 2000). Thus, the serendipitous presence of pyromellitic acid became important to the formation of the title compound, obtained as follows. Pyromellitic acid (0.0254 g, 0.1 mmol) was dissolved in methanol (5 ml) containing piperidine (0.034 g, 0.4 mmol). VO(acac)₂ (0.053 g, 0.2 mmol) dissolved in methanol (5 ml) was then added dropwise to the solution. The mixture was heated at reflux with stirring for 7 h. The reaction solution was filtered and concentrated by slow evaporation at room temperature for several days, and then orange crystals of the title compound of suitable size for X-ray analysis were obtained from the mixed solution.

S3. Refinement

All H atoms were positioned geometrically, with C—H distances of 0.97 (CH₂) or 0.96 Å (CH₃) and N—H distances of 0.90 Å, and they were then treated in riding mode, with U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(methyl C), but the torsion angles of the methyl groups were refined.

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994)); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids. [Symmetry code: (i) −x + 1, −y, −z + 1.]
	Fig. 2. A view of the three-dimensional hydrogen-bonding structure of (I). N2 H atoms join decavanadate units along the (101) plane and N1 H atoms bind along the [100] direction. Dotted lines indicate hydrogen bonds. [Symmetry codes: (i) −x + 2, −y, −z + 1; (ii) −x + 3/2, y + 1/2, −z + 1/2.]

Tetrapiperidinium di-µ-methoxy-di-µ₅-oxo-tetra-µ₃-oxo-dodeca-µ₂-oxo-octaoxodecavanadate

Crystal data

(C5H12N)4[V10(CH3O)2O26]	F(000) = 1336
Mr = 1332.09	Dx = 2.021 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5269 reflections
a = 10.546 (2) Å	θ = 2.3–23.3°
b = 12.950 (3) Å	µ = 2.13 mm^−1
c = 16.033 (3) Å	T = 296 K
β = 90.58 (3)°	Block, orange
V = 2189.5 (8) Å^3	0.22 × 0.18 × 0.14 mm
Z = 2

Data collection

Bruker APEX area-detector diffractometer	3957 independent reflections
Radiation source: fine-focus sealed tube	3226 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ϕ and ω scans	θmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan SADABS (Sheldrick, 2003)	h = −12→12
Tmin = 0.639, Tmax = 0.734	k = −10→15
11580 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 2.2417P] where P = (Fo^2 + 2Fc^2)/3
3957 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.73 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
V1	0.55955 (5)	0.16947 (4)	0.34238 (3)	0.03288 (15)
V2	0.29905 (5)	0.05938 (4)	0.40506 (3)	0.03148 (15)
V3	0.48827 (6)	−0.04982 (4)	0.28905 (3)	0.03491 (16)
V4	0.71648 (5)	−0.01575 (4)	0.40962 (3)	0.03057 (15)
V5	0.53063 (5)	0.12000 (4)	0.52507 (3)	0.02620 (14)
O1	0.5892 (2)	0.27549 (19)	0.29517 (15)	0.0455 (6)
O2	0.1520 (2)	0.0890 (2)	0.40532 (15)	0.0469 (6)
O3	0.4734 (3)	−0.1153 (2)	0.20495 (14)	0.0503 (7)
O4	0.8654 (2)	−0.0404 (2)	0.41318 (15)	0.0454 (6)
O5	0.5439 (2)	0.16155 (17)	0.62463 (13)	0.0343 (5)
O6	0.3717 (2)	0.18438 (17)	0.35708 (13)	0.0354 (5)
O7	0.5255 (2)	0.08004 (18)	0.25617 (13)	0.0358 (5)
O8	0.71665 (19)	0.11729 (17)	0.36063 (13)	0.0333 (5)
O9	0.5617 (2)	0.22085 (16)	0.46216 (13)	0.0341 (5)
O10	0.3178 (2)	−0.01297 (19)	0.31346 (13)	0.0381 (5)
O11	0.6598 (2)	−0.07721 (17)	0.31687 (13)	0.0350 (5)
O12	0.70014 (19)	0.05908 (16)	0.52069 (13)	0.0291 (5)
O13	0.35043 (19)	0.12186 (16)	0.51800 (13)	0.0289 (5)
O14	0.50738 (18)	0.02909 (15)	0.41969 (12)	0.0259 (4)
C1	0.3118 (5)	0.2851 (4)	0.3693 (3)	0.0753 (14)
H1A	0.2213	0.2772	0.3681	0.113*
H1B	0.3370	0.3311	0.3255	0.113*
H1C	0.3379	0.3130	0.4222	0.113*
N1	0.9223 (3)	0.1709 (3)	0.5428 (2)	0.0550 (9)
H1D	0.9806	0.1201	0.5440	0.066*
H1E	0.8481	0.1432	0.5259	0.066*
C2	0.9617 (4)	0.2507 (4)	0.4821 (3)	0.0681 (13)
H2A	0.9626	0.2209	0.4266	0.082*
H2B	1.0471	0.2735	0.4956	0.082*
C3	0.8744 (5)	0.3413 (4)	0.4826 (3)	0.0674 (12)
H3A	0.7912	0.3200	0.4628	0.081*
H3B	0.9059	0.3937	0.4449	0.081*
C4	0.8631 (5)	0.3867 (3)	0.5695 (3)	0.0652 (12)
H4A	0.9445	0.4141	0.5875	0.078*
H4B	0.8022	0.4428	0.5688	0.078*
C5	0.8209 (4)	0.3045 (4)	0.6289 (3)	0.0640 (12)
H5A	0.8179	0.3331	0.6847	0.077*
H5B	0.7359	0.2824	0.6136	0.077*
C6	0.9075 (4)	0.2132 (4)	0.6287 (3)	0.0656 (13)
H6A	0.9899	0.2334	0.6506	0.079*
H6B	0.8736	0.1600	0.6648	0.079*
N2	0.8609 (3)	0.1875 (2)	0.2268 (2)	0.0506 (8)
H2C	0.8684	0.2557	0.2364	0.061*
H2D	0.8126	0.1608	0.2674	0.061*
C7	0.9880 (4)	0.1401 (4)	0.2321 (3)	0.0593 (11)
H7A	1.0451	0.1770	0.1955	0.071*
H7B	1.0204	0.1464	0.2887	0.071*
C8	0.9851 (5)	0.0301 (4)	0.2082 (3)	0.0753 (14)
H8A	0.9371	−0.0084	0.2491	0.090*
H8B	1.0710	0.0031	0.2082	0.090*
C9	0.9248 (6)	0.0149 (4)	0.1214 (3)	0.0876 (17)
H9A	0.9754	0.0491	0.0795	0.105*
H9B	0.9206	−0.0581	0.1080	0.105*
C10	0.7934 (5)	0.0603 (4)	0.1226 (3)	0.0785 (15)
H10A	0.7545	0.0524	0.0679	0.094*
H10B	0.7423	0.0226	0.1623	0.094*
C11	0.7948 (4)	0.1724 (3)	0.1457 (3)	0.0602 (11)
H11A	0.8375	0.2117	0.1028	0.072*
H11B	0.7084	0.1976	0.1495	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.0343 (3)	0.0323 (3)	0.0321 (3)	0.0013 (2)	0.0042 (2)	0.0060 (2)
V2	0.0240 (3)	0.0392 (3)	0.0311 (3)	0.0025 (2)	−0.0030 (2)	0.0046 (2)
V3	0.0400 (3)	0.0383 (3)	0.0263 (3)	−0.0009 (3)	−0.0003 (2)	−0.0031 (2)
V4	0.0235 (3)	0.0373 (3)	0.0310 (3)	0.0028 (2)	0.0041 (2)	0.0030 (2)
V5	0.0262 (3)	0.0250 (3)	0.0274 (3)	−0.0012 (2)	0.0007 (2)	−0.0020 (2)
O1	0.0525 (15)	0.0389 (14)	0.0451 (14)	−0.0004 (12)	0.0047 (11)	0.0105 (11)
O2	0.0271 (12)	0.0667 (17)	0.0466 (14)	0.0085 (12)	−0.0058 (10)	0.0084 (13)
O3	0.0632 (17)	0.0550 (16)	0.0328 (13)	−0.0058 (13)	−0.0003 (12)	−0.0105 (12)
O4	0.0258 (12)	0.0628 (17)	0.0476 (14)	0.0078 (11)	0.0059 (10)	0.0110 (12)
O5	0.0385 (13)	0.0313 (12)	0.0329 (12)	−0.0032 (10)	−0.0011 (9)	−0.0045 (10)
O6	0.0348 (12)	0.0352 (12)	0.0363 (12)	0.0074 (10)	0.0006 (9)	0.0092 (10)
O7	0.0372 (13)	0.0424 (13)	0.0279 (11)	0.0016 (10)	−0.0002 (9)	0.0061 (10)
O8	0.0276 (11)	0.0378 (13)	0.0345 (12)	−0.0033 (9)	0.0047 (9)	0.0054 (10)
O9	0.0383 (13)	0.0277 (12)	0.0365 (12)	−0.0037 (10)	0.0030 (9)	0.0008 (9)
O10	0.0328 (12)	0.0499 (14)	0.0314 (12)	−0.0056 (11)	−0.0062 (9)	0.0008 (10)
O11	0.0370 (13)	0.0385 (13)	0.0297 (11)	0.0051 (10)	0.0063 (9)	−0.0007 (10)
O12	0.0226 (10)	0.0328 (12)	0.0318 (11)	−0.0036 (9)	−0.0026 (8)	0.0020 (9)
O13	0.0263 (11)	0.0293 (11)	0.0311 (11)	0.0045 (9)	0.0020 (8)	0.0006 (9)
O14	0.0231 (10)	0.0297 (11)	0.0249 (10)	−0.0006 (9)	0.0000 (8)	0.0011 (9)
C1	0.067 (3)	0.067 (3)	0.092 (4)	0.010 (2)	0.015 (3)	0.013 (3)
N1	0.0315 (16)	0.050 (2)	0.084 (2)	0.0024 (14)	−0.0167 (16)	−0.0081 (18)
C2	0.056 (3)	0.084 (3)	0.064 (3)	−0.004 (2)	0.018 (2)	−0.013 (3)
C3	0.081 (3)	0.065 (3)	0.056 (3)	0.008 (2)	0.006 (2)	0.009 (2)
C4	0.074 (3)	0.049 (3)	0.072 (3)	0.004 (2)	0.005 (2)	−0.007 (2)
C5	0.053 (3)	0.088 (3)	0.051 (2)	−0.021 (2)	0.0053 (19)	−0.025 (2)
C6	0.064 (3)	0.072 (3)	0.060 (3)	−0.020 (2)	−0.021 (2)	0.011 (2)
N2	0.0508 (19)	0.0467 (19)	0.0547 (19)	−0.0080 (15)	0.0131 (15)	0.0082 (15)
C7	0.055 (3)	0.067 (3)	0.056 (2)	0.003 (2)	0.0013 (19)	0.013 (2)
C8	0.087 (4)	0.061 (3)	0.079 (3)	0.017 (3)	0.007 (3)	0.016 (3)
C9	0.131 (5)	0.053 (3)	0.080 (4)	0.008 (3)	0.021 (3)	−0.009 (3)
C10	0.092 (4)	0.075 (3)	0.069 (3)	−0.027 (3)	−0.011 (3)	0.001 (3)
C11	0.052 (2)	0.067 (3)	0.061 (3)	−0.003 (2)	−0.001 (2)	0.014 (2)

Geometric parameters (Å, º)

V1—O1	1.600 (2)	N1—C6	1.491 (6)
V1—O6	2.007 (2)	N1—H1D	0.9000
V1—O7	1.836 (2)	N1—H1E	0.9000
V1—O8	1.810 (2)	C2—C3	1.491 (6)
V1—O9	2.033 (2)	C2—H2A	0.9700
V1—O14	2.271 (2)	C2—H2B	0.9700
V2—O2	1.598 (2)	C3—C4	1.517 (6)
V2—O6	1.952 (2)	C3—H3A	0.9700
V2—O10	1.755 (2)	C3—H3B	0.9700
V2—O12^i	1.942 (2)	C4—C5	1.498 (6)
V2—O13	2.051 (2)	C4—H4A	0.9700
V2—O14	2.242 (2)	C4—H4B	0.9700
V3—O3	1.600 (2)	C5—C6	1.494 (6)
V3—O5^i	2.033 (2)	C5—H5A	0.9700
V3—O7	1.807 (2)	C5—H5B	0.9700
V3—O10	1.904 (2)	C6—H6A	0.9700
V3—O11	1.893 (2)	C6—H6B	0.9700
V3—O14	2.337 (2)	N2—C7	1.476 (5)
V4—O4	1.603 (2)	N2—C11	1.481 (5)
V4—O8	1.893 (2)	N2—H2C	0.9000
V4—O11	1.784 (2)	N2—H2D	0.9000
V4—O12	2.036 (2)	C7—C8	1.475 (6)
V4—O13^i	1.936 (2)	C7—H7A	0.9700
V4—O14	2.288 (2)	C7—H7B	0.9700
V5—O5	1.689 (2)	C8—C9	1.538 (7)
V5—O9	1.684 (2)	C8—H8A	0.9700
V5—O12	1.956 (2)	C8—H8B	0.9700
V5—O13	1.903 (2)	C9—C10	1.505 (7)
V5—O14	2.072 (2)	C9—H9A	0.9700
V5—O14^i	2.163 (2)	C9—H9B	0.9700
O6—C1	1.463 (5)	C10—C11	1.499 (6)
C1—H1A	0.9600	C10—H10A	0.9700
C1—H1B	0.9600	C10—H10B	0.9700
C1—H1C	0.9600	C11—H11A	0.9700
N1—C2	1.482 (6)	C11—H11B	0.9700
O1—V1—O8	102.36 (12)	O14—V4—V3	48.54 (5)
O1—V1—O7	102.87 (12)	V2^i—V4—V3	122.35 (3)
O8—V1—O7	93.33 (10)	V1—V4—V3	59.04 (2)
O1—V1—O6	99.82 (11)	O9—V5—O5	107.71 (11)
O8—V1—O6	156.91 (9)	O9—V5—O13	98.90 (10)
O7—V1—O6	87.89 (10)	O5—V5—O13	97.20 (10)
O1—V1—O9	99.54 (11)	O9—V5—O12	96.19 (10)
O8—V1—O9	88.16 (10)	O5—V5—O12	95.48 (10)
O7—V1—O9	156.66 (10)	O13—V5—O12	156.29 (9)
O6—V1—O9	81.90 (10)	O9—V5—O14	88.53 (9)
O1—V1—O14	174.02 (11)	O5—V5—O14	163.69 (10)
O8—V1—O14	80.76 (8)	O13—V5—O14	81.30 (9)
O7—V1—O14	81.91 (9)	O12—V5—O14	80.92 (8)
O6—V1—O14	76.58 (8)	O9—V5—O14^i	167.20 (9)
O9—V1—O14	75.33 (8)	O5—V5—O14^i	84.91 (9)
O1—V1—V5	131.58 (9)	O13—V5—O14^i	81.18 (8)
O8—V1—V5	82.24 (7)	O12—V5—O14^i	80.09 (8)
O7—V1—V5	125.18 (7)	O14—V5—O14^i	78.81 (8)
O6—V1—V5	78.27 (7)	O9—V5—V1	39.81 (7)
O9—V1—V5	32.04 (6)	O5—V5—V1	147.33 (8)
O14—V1—V5	43.34 (5)	O13—V5—V1	92.88 (7)
O1—V1—V3	135.51 (10)	O12—V5—V1	87.10 (7)
O8—V1—V3	85.44 (7)	O14—V5—V1	48.79 (6)
O7—V1—V3	32.63 (7)	O14^i—V5—V1	127.44 (6)
O6—V1—V3	83.22 (7)	V5—O5—V3^i	113.82 (11)
O9—V1—V3	124.66 (6)	C1—O6—V1	122.0 (2)
O14—V1—V3	49.37 (5)	C1—O6—V2	121.0 (2)
V5—V1—V3	92.71 (2)	V2—O6—V1	111.01 (10)
O1—V1—V4	136.23 (10)	V3—O7—V1	114.14 (11)
O8—V1—V4	33.99 (7)	V1—O8—V4	113.70 (11)
O7—V1—V4	82.74 (7)	V5—O9—V1	108.15 (11)
O6—V1—V4	123.89 (6)	V2—O10—V3	114.87 (12)
O9—V1—V4	85.63 (7)	V4—O11—V3	115.08 (11)
O14—V1—V4	47.36 (5)	V2^i—O12—V5	107.16 (10)
V5—V1—V4	63.71 (2)	V2^i—O12—V4	99.22 (9)
V3—V1—V4	60.51 (2)	V5—O12—V4	107.99 (10)
O2—V2—O10	104.37 (12)	V5—O13—V4^i	108.97 (10)
O2—V2—O12^i	100.75 (11)	V5—O13—V2	107.60 (10)
O10—V2—O12^i	95.25 (10)	V4^i—O13—V2	98.89 (9)
O2—V2—O6	100.76 (12)	V5—O14—V5^i	101.19 (8)
O10—V2—O6	93.72 (10)	V5—O14—V2	95.38 (8)
O12^i—V2—O6	153.81 (9)	V5^i—O14—V2	90.78 (7)
O2—V2—O13	98.67 (11)	V5—O14—V1	87.88 (8)
O10—V2—O13	156.68 (10)	V5^i—O14—V1	169.99 (10)
O12^i—V2—O13	76.75 (9)	V2—O14—V1	92.61 (7)
O6—V2—O13	85.39 (9)	V5—O14—V4	95.48 (8)
O2—V2—O14	172.79 (11)	V5^i—O14—V4	89.14 (7)
O10—V2—O14	82.84 (9)	V2—O14—V4	168.95 (10)
O12^i—V2—O14	78.42 (8)	V1—O14—V4	85.74 (7)
O6—V2—O14	78.35 (8)	V5—O14—V3	170.98 (10)
O13—V2—O14	74.14 (8)	V5^i—O14—V3	87.83 (7)
O2—V2—V4^i	88.87 (9)	V2—O14—V3	84.68 (7)
O10—V2—V4^i	136.78 (8)	V1—O14—V3	83.11 (7)
O12^i—V2—V4^i	41.55 (6)	V4—O14—V3	84.28 (7)
O6—V2—V4^i	124.49 (7)	O6—C1—H1A	109.5
O13—V2—V4^i	39.14 (6)	O6—C1—H1B	109.5
O14—V2—V4^i	85.84 (6)	H1A—C1—H1B	109.5
O2—V2—V3	138.21 (10)	O6—C1—H1C	109.5
O10—V2—V3	34.06 (7)	H1A—C1—H1C	109.5
O12^i—V2—V3	90.49 (7)	H1B—C1—H1C	109.5
O6—V2—V3	83.31 (7)	C2—N1—C6	112.5 (3)
O13—V2—V3	123.12 (6)	C2—N1—H1D	109.1
O14—V2—V3	48.97 (5)	C6—N1—H1D	109.1
V4^i—V2—V3	123.19 (3)	C2—N1—H1E	109.1
O3—V3—O7	105.52 (12)	C6—N1—H1E	109.1
O3—V3—O11	100.65 (12)	H1D—N1—H1E	107.8
O7—V3—O11	91.91 (10)	N1—C2—C3	111.5 (3)
O3—V3—O10	102.78 (12)	N1—C2—H2A	109.3
O7—V3—O10	92.00 (10)	C3—C2—H2A	109.3
O11—V3—O10	154.25 (10)	N1—C2—H2B	109.3
O3—V3—O5^i	100.41 (11)	C3—C2—H2B	109.3
O7—V3—O5^i	154.07 (9)	H2A—C2—H2B	108.0
O11—V3—O5^i	82.64 (10)	C2—C3—C4	111.4 (4)
O10—V3—O5^i	82.77 (10)	C2—C3—H3A	109.4
O3—V3—O14	173.80 (11)	C4—C3—H3A	109.4
O7—V3—O14	80.65 (9)	C2—C3—H3B	109.4
O11—V3—O14	78.30 (8)	C4—C3—H3B	109.4
O10—V3—O14	77.25 (9)	H3A—C3—H3B	108.0
O5^i—V3—O14	73.42 (8)	C5—C4—C3	109.6 (4)
O3—V3—V1	138.61 (10)	C5—C4—H4A	109.8
O7—V3—V1	33.23 (7)	C3—C4—H4A	109.8
O11—V3—V1	82.90 (7)	C5—C4—H4B	109.8
O10—V3—V1	86.54 (7)	C3—C4—H4B	109.8
O5^i—V3—V1	120.86 (6)	H4A—C4—H4B	108.2
O14—V3—V1	47.52 (5)	C6—C5—C4	112.0 (4)
O3—V3—V2	133.85 (10)	C6—C5—H5A	109.2
O7—V3—V2	83.86 (7)	C4—C5—H5A	109.2
O11—V3—V2	124.51 (7)	C6—C5—H5B	109.2
O10—V3—V2	31.07 (7)	C4—C5—H5B	109.2
O5^i—V3—V2	78.61 (7)	H5A—C5—H5B	107.9
O14—V3—V2	46.35 (5)	N1—C6—C5	111.2 (3)
V1—V3—V2	64.17 (2)	N1—C6—H6A	109.4
O3—V3—V4	132.03 (10)	C5—C6—H6A	109.4
O7—V3—V4	83.11 (7)	N1—C6—H6B	109.4
O11—V3—V4	31.39 (7)	C5—C6—H6B	109.4
O10—V3—V4	124.34 (7)	H6A—C6—H6B	108.0
O5^i—V3—V4	79.09 (6)	C7—N2—C11	114.5 (3)
O14—V3—V4	47.18 (5)	C7—N2—H2C	108.6
V1—V3—V4	60.449 (19)	C11—N2—H2C	108.6
V2—V3—V4	93.53 (2)	C7—N2—H2D	108.6
O4—V4—O11	105.11 (12)	C11—N2—H2D	108.6
O4—V4—O8	100.99 (11)	H2C—N2—H2D	107.6
O11—V4—O8	93.54 (10)	C8—C7—N2	111.7 (4)
O4—V4—O13^i	101.56 (11)	C8—C7—H7A	109.3
O11—V4—O13^i	93.56 (10)	N2—C7—H7A	109.3
O8—V4—O13^i	153.66 (9)	C8—C7—H7B	109.3
O4—V4—O12	98.91 (11)	N2—C7—H7B	109.3
O11—V4—O12	155.59 (9)	H7A—C7—H7B	107.9
O8—V4—O12	85.99 (9)	C7—C8—C9	111.4 (4)
O13^i—V4—O12	77.24 (9)	C7—C8—H8A	109.3
O4—V4—O14	173.09 (11)	C9—C8—H8A	109.3
O11—V4—O14	81.79 (9)	C7—C8—H8B	109.3
O8—V4—O14	78.65 (8)	C9—C8—H8B	109.3
O13^i—V4—O14	77.32 (8)	H8A—C8—H8B	108.0
O12—V4—O14	74.18 (8)	C10—C9—C8	108.1 (4)
O4—V4—V2^i	89.46 (9)	C10—C9—H9A	110.1
O11—V4—V2^i	135.49 (8)	C8—C9—H9A	110.1
O8—V4—V2^i	125.21 (7)	C10—C9—H9B	110.1
O13^i—V4—V2^i	41.97 (6)	C8—C9—H9B	110.1
O12—V4—V2^i	39.23 (6)	H9A—C9—H9B	108.4
O14—V4—V2^i	85.21 (6)	C11—C10—C9	112.0 (4)
O4—V4—V1	133.26 (9)	C11—C10—H10A	109.2
O11—V4—V1	83.24 (8)	C9—C10—H10A	109.2
O8—V4—V1	32.31 (6)	C11—C10—H10B	109.2
O13^i—V4—V1	124.11 (6)	C9—C10—H10B	109.2
O12—V4—V1	83.47 (6)	H10A—C10—H10B	107.9
O14—V4—V1	46.91 (5)	N2—C11—C10	110.4 (4)
V2^i—V4—V1	116.81 (3)	N2—C11—H11A	109.6
O4—V4—V3	138.36 (10)	C10—C11—H11A	109.6
O11—V4—V3	33.53 (7)	N2—C11—H11B	109.6
O8—V4—V3	82.81 (7)	C10—C11—H11B	109.6
O13^i—V4—V3	89.28 (7)	H11A—C11—H11B	108.1
O12—V4—V3	122.72 (6)
O1—V1—V3—O3	6.1 (2)	O2—V2—O6—V1	−177.08 (12)
O8—V1—V3—O3	−96.96 (17)	O10—V2—O6—V1	−71.68 (12)
O7—V1—V3—O3	6.5 (2)	O12^i—V2—O6—V1	38.2 (3)
O6—V1—V3—O3	103.20 (17)	O13—V2—O6—V1	84.96 (11)
O9—V1—V3—O3	178.44 (17)	O14—V2—O6—V1	10.22 (10)
O14—V1—V3—O3	−178.68 (17)	V4^i—V2—O6—V1	86.83 (11)
V5—V1—V3—O3	−178.96 (15)	V3—V2—O6—V1	−39.19 (9)
V4—V1—V3—O3	−121.38 (16)	O1—V1—O6—C1	−32.4 (3)
O1—V1—V3—O7	−0.43 (18)	O8—V1—O6—C1	131.3 (3)
O8—V1—V3—O7	−103.45 (15)	O7—V1—O6—C1	−135.1 (3)
O6—V1—V3—O7	96.71 (15)	O9—V1—O6—C1	65.9 (3)
O9—V1—V3—O7	171.95 (15)	O14—V1—O6—C1	142.7 (3)
O14—V1—V3—O7	174.83 (15)	V5—V1—O6—C1	98.3 (3)
V5—V1—V3—O7	174.56 (13)	V3—V1—O6—C1	−167.5 (3)
V4—V1—V3—O7	−127.87 (13)	V4—V1—O6—C1	145.1 (3)
O1—V1—V3—O11	104.13 (15)	O1—V1—O6—V2	174.73 (13)
O8—V1—V3—O11	1.10 (9)	O8—V1—O6—V2	−21.5 (3)
O7—V1—V3—O11	104.55 (15)	O7—V1—O6—V2	72.03 (12)
O6—V1—V3—O11	−158.74 (9)	O9—V1—O6—V2	−86.92 (11)
O9—V1—V3—O11	−83.49 (11)	O14—V1—O6—V2	−10.16 (10)
O14—V1—V3—O11	−80.62 (9)	V5—V1—O6—V2	−54.58 (9)
V5—V1—V3—O11	−80.89 (7)	V3—V1—O6—V2	39.62 (9)
V4—V1—V3—O11	−23.32 (7)	V4—V1—O6—V2	−7.77 (14)
O1—V1—V3—O10	−99.41 (15)	O3—V3—O7—V1	−175.55 (13)
O8—V1—V3—O10	157.57 (9)	O11—V3—O7—V1	−73.95 (13)
O7—V1—V3—O10	−98.98 (15)	O10—V3—O7—V1	80.59 (13)
O6—V1—V3—O10	−2.27 (9)	O5^i—V3—O7—V1	3.1 (3)
O9—V1—V3—O10	72.97 (11)	O14—V3—O7—V1	3.86 (11)
O14—V1—V3—O10	75.85 (10)	V2—V3—O7—V1	50.56 (11)
V5—V1—V3—O10	75.58 (7)	V4—V3—O7—V1	−43.76 (10)
V4—V1—V3—O10	133.15 (7)	O1—V1—O7—V3	179.69 (13)
O1—V1—V3—O5^i	−178.86 (15)	O8—V1—O7—V3	76.20 (13)
O8—V1—V3—O5^i	78.11 (10)	O6—V1—O7—V3	−80.71 (13)
O7—V1—V3—O5^i	−178.44 (15)	O9—V1—O7—V3	−16.9 (3)
O6—V1—V3—O5^i	−81.73 (10)	O14—V1—O7—V3	−3.96 (11)
O9—V1—V3—O5^i	−6.48 (12)	V5—V1—O7—V3	−6.66 (16)
O14—V1—V3—O5^i	−3.61 (10)	V4—V1—O7—V3	43.84 (10)
V5—V1—V3—O5^i	−3.88 (8)	O1—V1—O8—V4	−175.72 (13)
V4—V1—V3—O5^i	53.69 (8)	O7—V1—O8—V4	−71.76 (13)
O1—V1—V3—O14	−175.25 (15)	O6—V1—O8—V4	20.7 (3)
O8—V1—V3—O14	81.72 (10)	O9—V1—O8—V4	84.91 (12)
O7—V1—V3—O14	−174.83 (15)	O14—V1—O8—V4	9.48 (11)
O6—V1—V3—O14	−78.12 (9)	V5—V1—O8—V4	53.30 (10)
O9—V1—V3—O14	−2.87 (10)	V3—V1—O8—V4	−40.07 (10)
V5—V1—V3—O14	−0.27 (6)	O4—V4—O8—V1	177.56 (13)
V4—V1—V3—O14	57.30 (7)	O11—V4—O8—V1	71.42 (13)
O1—V1—V3—V2	−121.88 (14)	O13^i—V4—O8—V1	−34.0 (3)
O8—V1—V3—V2	135.10 (7)	O12—V4—O8—V1	−84.12 (12)
O7—V1—V3—V2	−121.45 (13)	O14—V4—O8—V1	−9.47 (11)
O6—V1—V3—V2	−24.75 (6)	V2^i—V4—O8—V1	−85.24 (12)
O9—V1—V3—V2	50.50 (8)	V3—V4—O8—V1	39.58 (10)
O14—V1—V3—V2	53.37 (7)	O5—V5—O9—V1	175.68 (10)
V5—V1—V3—V2	53.10 (3)	O13—V5—O9—V1	−83.76 (11)
V4—V1—V3—V2	110.67 (2)	O12—V5—O9—V1	77.89 (11)
O1—V1—V3—V4	127.45 (14)	O14—V5—O9—V1	−2.81 (10)
O8—V1—V3—V4	24.42 (7)	O14^i—V5—O9—V1	5.6 (5)
O7—V1—V3—V4	127.87 (13)	O1—V1—O9—V5	179.50 (13)
O6—V1—V3—V4	−135.42 (7)	O8—V1—O9—V5	−78.27 (12)
O9—V1—V3—V4	−60.17 (8)	O7—V1—O9—V5	15.9 (3)
O14—V1—V3—V4	−57.30 (7)	O6—V1—O9—V5	80.82 (12)
V5—V1—V3—V4	−57.57 (3)	O14—V1—O9—V5	2.65 (10)
O2—V2—V3—O3	−9.5 (2)	V3—V1—O9—V5	4.90 (14)
O10—V2—V3—O3	−1.37 (19)	V4—V1—O9—V5	−44.32 (10)
O12^i—V2—V3—O3	97.29 (15)	O2—V2—O10—V3	174.39 (14)
O6—V2—V3—O3	−108.22 (15)	O12^i—V2—O10—V3	−83.08 (13)
O13—V2—V3—O3	171.75 (15)	O6—V2—O10—V3	72.28 (13)
O14—V2—V3—O3	171.42 (15)	O13—V2—O10—V3	−14.7 (3)
V4^i—V2—V3—O3	124.58 (14)	O14—V2—O10—V3	−5.47 (12)
O2—V2—V3—O7	96.11 (16)	V4^i—V2—O10—V3	−81.56 (15)
O10—V2—V3—O7	104.28 (15)	O3—V3—O10—V2	178.99 (14)
O12^i—V2—V3—O7	−157.05 (9)	O7—V3—O10—V2	−74.60 (14)
O6—V2—V3—O7	−2.57 (9)	O11—V3—O10—V2	24.0 (3)
O13—V2—V3—O7	−82.60 (10)	O5^i—V3—O10—V2	79.90 (13)
O14—V2—V3—O7	−82.93 (10)	O14—V3—O10—V2	5.34 (12)
V4^i—V2—V3—O7	−129.76 (7)	V1—V3—O10—V2	−41.81 (12)
O2—V2—V3—O11	−175.80 (17)	V4—V3—O10—V2	8.42 (17)
O10—V2—V3—O11	−167.63 (17)	O4—V4—O11—V3	−173.70 (13)
O12^i—V2—V3—O11	−68.97 (11)	O8—V4—O11—V3	−71.32 (13)
O6—V2—V3—O11	85.52 (11)	O13^i—V4—O11—V3	83.31 (13)
O13—V2—V3—O11	5.49 (12)	O12—V4—O11—V3	16.8 (3)
O14—V2—V3—O11	5.16 (11)	O14—V4—O11—V3	6.67 (11)
V4^i—V2—V3—O11	−41.67 (9)	V2^i—V4—O11—V3	81.19 (15)
O2—V2—V3—O10	−8.2 (2)	V1—V4—O11—V3	−40.64 (10)
O12^i—V2—V3—O10	98.66 (15)	O3—V3—O11—V4	179.63 (14)
O6—V2—V3—O10	−106.85 (15)	O7—V3—O11—V4	73.44 (13)
O13—V2—V3—O10	173.12 (16)	O10—V3—O11—V4	−25.2 (3)
O14—V2—V3—O10	172.79 (16)	O5^i—V3—O11—V4	−81.11 (13)
V4^i—V2—V3—O10	125.96 (14)	O14—V3—O11—V4	−6.60 (11)
O2—V2—V3—O5^i	−103.09 (16)	V1—V3—O11—V4	41.39 (11)
O10—V2—V3—O5^i	−94.92 (15)	V2—V3—O11—V4	−10.41 (16)
O12^i—V2—V3—O5^i	3.75 (8)	O9—V5—O12—V2^i	176.56 (10)
O6—V2—V3—O5^i	158.23 (9)	O5—V5—O12—V2^i	68.04 (12)
O13—V2—V3—O5^i	78.20 (10)	O13—V5—O12—V2^i	−54.1 (3)
O14—V2—V3—O5^i	77.87 (9)	O14—V5—O12—V2^i	−95.93 (10)
V4^i—V2—V3—O5^i	31.04 (7)	O14^i—V5—O12—V2^i	−15.81 (9)
O2—V2—V3—O14	179.03 (16)	V1—V5—O12—V2^i	−144.63 (9)
O10—V2—V3—O14	−172.79 (16)	O9—V5—O12—V4	−77.38 (11)
O12^i—V2—V3—O14	−74.13 (9)	O5—V5—O12—V4	174.10 (10)
O6—V2—V3—O14	80.36 (9)	O13—V5—O12—V4	52.0 (3)
O13—V2—V3—O14	0.33 (10)	O14—V5—O12—V4	10.13 (9)
V4^i—V2—V3—O14	−46.84 (7)	O14^i—V5—O12—V4	90.25 (10)
O2—V2—V3—V1	124.15 (15)	V1—V5—O12—V4	−38.57 (8)
O10—V2—V3—V1	132.33 (14)	O4—V4—O12—V2^i	−78.04 (12)
O12^i—V2—V3—V1	−129.01 (6)	O11—V4—O12—V2^i	91.7 (2)
O6—V2—V3—V1	25.48 (7)	O8—V4—O12—V2^i	−178.56 (9)
O13—V2—V3—V1	−54.55 (7)	O13^i—V4—O12—V2^i	21.89 (8)
O14—V2—V3—V1	−54.88 (7)	O14—V4—O12—V2^i	102.12 (9)
V4^i—V2—V3—V1	−101.72 (3)	V1—V4—O12—V2^i	149.09 (7)
O2—V2—V3—V4	178.79 (15)	V3—V4—O12—V2^i	102.63 (8)
O10—V2—V3—V4	−173.04 (14)	O4—V4—O12—V5	170.43 (12)
O12^i—V2—V3—V4	−74.38 (6)	O11—V4—O12—V5	−19.8 (3)
O6—V2—V3—V4	80.11 (7)	O8—V4—O12—V5	69.92 (10)
O13—V2—V3—V4	0.08 (7)	O13^i—V4—O12—V5	−89.64 (10)
O14—V2—V3—V4	−0.25 (7)	O14—V4—O12—V5	−9.41 (8)
V4^i—V2—V3—V4	−47.08 (4)	V2^i—V4—O12—V5	−111.53 (12)
O1—V1—V4—O4	2.75 (19)	V1—V4—O12—V5	37.56 (8)
O8—V1—V4—O4	−3.29 (17)	V3—V4—O12—V5	−8.89 (12)
O7—V1—V4—O4	103.80 (15)	O9—V5—O13—V4^i	−177.11 (11)
O6—V1—V4—O4	−173.69 (15)	O5—V5—O13—V4^i	−67.84 (12)
O9—V1—V4—O4	−96.48 (15)	O12—V5—O13—V4^i	54.0 (3)
O14—V1—V4—O4	−170.52 (15)	O14—V5—O13—V4^i	95.76 (10)
V5—V1—V4—O4	−120.91 (14)	O14^i—V5—O13—V4^i	15.84 (10)
V3—V1—V4—O4	129.21 (13)	V1—V5—O13—V4^i	143.30 (8)
O1—V1—V4—O11	−101.65 (15)	O9—V5—O13—V2	76.59 (11)
O8—V1—V4—O11	−107.70 (15)	O5—V5—O13—V2	−174.13 (10)
O7—V1—V4—O11	−0.61 (10)	O12—V5—O13—V2	−52.3 (3)
O6—V1—V4—O11	81.91 (11)	O14—V5—O13—V2	−10.53 (9)
O9—V1—V4—O11	159.11 (9)	O14^i—V5—O13—V2	−90.45 (10)
O14—V1—V4—O11	85.07 (10)	V1—V5—O13—V2	37.01 (8)
V5—V1—V4—O11	134.69 (7)	O2—V2—O13—V5	−169.39 (12)
V3—V1—V4—O11	24.81 (7)	O10—V2—O13—V5	19.5 (3)
O1—V1—V4—O8	6.04 (18)	O12^i—V2—O13—V5	91.52 (10)
O7—V1—V4—O8	107.09 (15)	O6—V2—O13—V5	−69.19 (11)
O6—V1—V4—O8	−170.40 (15)	O14—V2—O13—V5	9.99 (9)
O9—V1—V4—O8	−93.19 (14)	V4^i—V2—O13—V5	113.26 (13)
O14—V1—V4—O8	−167.23 (14)	V3—V2—O13—V5	9.73 (12)
V5—V1—V4—O8	−117.62 (13)	O2—V2—O13—V4^i	77.35 (12)
V3—V1—V4—O8	132.50 (13)	O10—V2—O13—V4^i	−93.8 (3)
O1—V1—V4—O13^i	168.63 (15)	O12^i—V2—O13—V4^i	−21.74 (8)
O8—V1—V4—O13^i	162.58 (15)	O6—V2—O13—V4^i	177.55 (9)
O7—V1—V4—O13^i	−90.33 (11)	O14—V2—O13—V4^i	−103.26 (9)
O6—V1—V4—O13^i	−7.81 (12)	V3—V2—O13—V4^i	−103.52 (8)
O9—V1—V4—O13^i	69.39 (10)	O9—V5—O14—V5^i	178.11 (10)
O14—V1—V4—O13^i	−4.65 (10)	O5—V5—O14—V5^i	3.2 (4)
V5—V1—V4—O13^i	44.97 (8)	O13—V5—O14—V5^i	−82.65 (9)
V3—V1—V4—O13^i	−64.91 (8)	O12—V5—O14—V5^i	81.61 (9)
O1—V1—V4—O12	98.87 (15)	O14^i—V5—O14—V5^i	0.0
O8—V1—V4—O12	92.83 (14)	V1—V5—O14—V5^i	175.72 (11)
O7—V1—V4—O12	−160.08 (9)	O9—V5—O14—V2	−90.03 (10)
O6—V1—V4—O12	−77.57 (10)	O5—V5—O14—V2	95.1 (3)
O9—V1—V4—O12	−0.37 (8)	O13—V5—O14—V2	9.21 (8)
O14—V1—V4—O12	−74.41 (9)	O12—V5—O14—V2	173.47 (9)
V5—V1—V4—O12	−24.79 (6)	O14^i—V5—O14—V2	91.86 (9)
V3—V1—V4—O12	−134.67 (6)	V1—V5—O14—V2	−92.42 (8)
O1—V1—V4—O14	173.28 (15)	O9—V5—O14—V1	2.39 (9)
O8—V1—V4—O14	167.23 (14)	O5—V5—O14—V1	−172.5 (3)
O7—V1—V4—O14	−85.67 (10)	O13—V5—O14—V1	101.63 (8)
O6—V1—V4—O14	−3.16 (10)	O12—V5—O14—V1	−94.11 (8)
O9—V1—V4—O14	74.04 (9)	O14^i—V5—O14—V1	−175.72 (11)
V5—V1—V4—O14	49.62 (7)	O9—V5—O14—V4	87.90 (9)
V3—V1—V4—O14	−60.26 (7)	O5—V5—O14—V4	−87.0 (3)
O1—V1—V4—V2^i	120.22 (14)	O13—V5—O14—V4	−172.86 (9)
O8—V1—V4—V2^i	114.17 (13)	O12—V5—O14—V4	−8.61 (8)
O7—V1—V4—V2^i	−138.74 (7)	O14^i—V5—O14—V4	−90.21 (9)
O6—V1—V4—V2^i	−56.22 (9)	V1—V5—O14—V4	85.51 (7)
O9—V1—V4—V2^i	20.98 (7)	O10—V2—O14—V5	175.00 (10)
O14—V1—V4—V2^i	−53.06 (7)	O12^i—V2—O14—V5	−88.12 (9)
V5—V1—V4—V2^i	−3.44 (2)	O6—V2—O14—V5	79.69 (9)
V3—V1—V4—V2^i	−113.32 (3)	O13—V2—O14—V5	−8.78 (8)
O1—V1—V4—V3	−126.46 (14)	V4^i—V2—O14—V5	−46.80 (6)
O8—V1—V4—V3	−132.50 (13)	V3—V2—O14—V5	170.94 (10)
O7—V1—V4—V3	−25.41 (7)	O10—V2—O14—V5^i	−83.68 (10)
O6—V1—V4—V3	57.10 (8)	O12^i—V2—O14—V5^i	13.20 (8)
O9—V1—V4—V3	134.30 (7)	O6—V2—O14—V5^i	−178.99 (9)
O14—V1—V4—V3	60.26 (7)	O13—V2—O14—V5^i	92.54 (8)
V5—V1—V4—V3	109.88 (3)	V4^i—V2—O14—V5^i	54.52 (5)
O3—V3—V4—O4	8.67 (19)	V3—V2—O14—V5^i	−87.74 (7)
O7—V3—V4—O4	−96.04 (16)	O10—V2—O14—V1	86.89 (10)
O11—V3—V4—O4	9.17 (19)	O12^i—V2—O14—V1	−176.23 (9)
O10—V3—V4—O4	176.24 (16)	O6—V2—O14—V1	−8.42 (8)
O5^i—V3—V4—O4	102.91 (16)	O13—V2—O14—V1	−96.89 (8)
O14—V3—V4—O4	−179.66 (16)	V4^i—V2—O14—V1	−134.91 (6)
V1—V3—V4—O4	−121.87 (14)	V3—V2—O14—V1	82.83 (7)
V2—V3—V4—O4	−179.41 (14)	O10—V2—O14—V4	5.8 (5)
O3—V3—V4—O11	−0.50 (18)	O12^i—V2—O14—V4	102.7 (5)
O7—V3—V4—O11	−105.21 (15)	O6—V2—O14—V4	−89.5 (5)
O10—V3—V4—O11	167.07 (16)	O13—V2—O14—V4	−178.0 (5)
O5^i—V3—V4—O11	93.74 (15)	V4^i—V2—O14—V4	144.0 (5)
O14—V3—V4—O11	171.17 (15)	V3—V2—O14—V4	1.8 (5)
V1—V3—V4—O11	−131.04 (13)	O10—V2—O14—V3	4.06 (9)
V2—V3—V4—O11	171.42 (13)	O12^i—V2—O14—V3	100.95 (8)
O3—V3—V4—O8	107.15 (15)	O6—V2—O14—V3	−91.25 (8)
O7—V3—V4—O8	2.43 (9)	O13—V2—O14—V3	−179.71 (8)
O11—V3—V4—O8	107.64 (15)	V4^i—V2—O14—V3	142.26 (5)
O10—V3—V4—O8	−85.28 (11)	O8—V1—O14—V5	88.47 (9)
O5^i—V3—V4—O8	−158.61 (9)	O7—V1—O14—V5	−176.79 (9)
O14—V3—V4—O8	−81.19 (9)	O6—V1—O14—V5	−87.04 (9)
V1—V3—V4—O8	−23.40 (7)	O9—V1—O14—V5	−2.05 (8)
V2—V3—V4—O8	−80.94 (7)	V3—V1—O14—V5	−179.60 (9)
O3—V3—V4—O13^i	−98.04 (15)	V4—V1—O14—V5	95.66 (8)
O7—V3—V4—O13^i	157.25 (9)	O8—V1—O14—V5^i	−66.6 (6)
O11—V3—V4—O13^i	−97.54 (15)	O7—V1—O14—V5^i	28.1 (6)
O10—V3—V4—O13^i	69.53 (11)	O6—V1—O14—V5^i	117.9 (6)
O5^i—V3—V4—O13^i	−3.80 (9)	O9—V1—O14—V5^i	−157.2 (6)
O14—V3—V4—O13^i	73.63 (9)	V5—V1—O14—V5^i	−155.1 (6)
V1—V3—V4—O13^i	131.42 (6)	V3—V1—O14—V5^i	25.3 (5)
V2—V3—V4—O13^i	73.88 (6)	V4—V1—O14—V5^i	−59.4 (5)
O3—V3—V4—O12	−172.33 (15)	O8—V1—O14—V2	−176.24 (9)
O7—V3—V4—O12	82.95 (10)	O7—V1—O14—V2	−81.50 (9)
O11—V3—V4—O12	−171.84 (15)	O6—V1—O14—V2	8.25 (8)
O10—V3—V4—O12	−4.76 (12)	O9—V1—O14—V2	93.24 (9)
O5^i—V3—V4—O12	−78.09 (10)	V5—V1—O14—V2	95.29 (8)
O14—V3—V4—O12	−0.66 (10)	V3—V1—O14—V2	−84.31 (7)
V1—V3—V4—O12	57.12 (7)	V4—V1—O14—V2	−169.05 (10)
V2—V3—V4—O12	−0.42 (8)	O8—V1—O14—V4	−7.19 (8)
O3—V3—V4—O14	−171.67 (15)	O7—V1—O14—V4	87.55 (9)
O7—V3—V4—O14	83.62 (10)	O6—V1—O14—V4	177.30 (9)
O11—V3—V4—O14	−171.17 (15)	O9—V1—O14—V4	−97.71 (9)
O10—V3—V4—O14	−4.10 (11)	V5—V1—O14—V4	−95.66 (8)
O5^i—V3—V4—O14	−77.43 (9)	V3—V1—O14—V4	84.74 (7)
V1—V3—V4—O14	57.79 (7)	O8—V1—O14—V3	−91.93 (9)
V2—V3—V4—O14	0.25 (7)	O7—V1—O14—V3	2.81 (8)
O3—V3—V4—V2^i	−125.40 (13)	O6—V1—O14—V3	92.57 (8)
O7—V3—V4—V2^i	129.88 (7)	O9—V1—O14—V3	177.56 (8)
O11—V3—V4—V2^i	−124.91 (13)	V5—V1—O14—V3	179.60 (9)
O10—V3—V4—V2^i	42.17 (10)	V4—V1—O14—V3	−84.74 (7)
O5^i—V3—V4—V2^i	−31.16 (7)	O11—V4—O14—V5	−175.85 (10)
O14—V3—V4—V2^i	46.26 (7)	O8—V4—O14—V5	−80.53 (9)
V1—V3—V4—V2^i	104.05 (3)	O13^i—V4—O14—V5	88.60 (9)
V2—V3—V4—V2^i	46.51 (4)	O12—V4—O14—V5	8.48 (8)
O3—V3—V4—V1	130.55 (13)	V2^i—V4—O14—V5	46.84 (6)
O7—V3—V4—V1	25.83 (7)	V1—V4—O14—V5	−87.45 (8)
O11—V3—V4—V1	131.04 (13)	V3—V4—O14—V5	−170.94 (10)
O10—V3—V4—V1	−61.88 (9)	O11—V4—O14—V5^i	82.99 (9)
O5^i—V3—V4—V1	−135.21 (7)	O8—V4—O14—V5^i	178.30 (9)
O14—V3—V4—V1	−57.79 (7)	O13^i—V4—O14—V5^i	−12.56 (8)
V2—V3—V4—V1	−57.54 (2)	O12—V4—O14—V5^i	−92.68 (8)
O1—V1—V5—O9	−0.66 (17)	V2^i—V4—O14—V5^i	−54.33 (5)
O8—V1—V5—O9	99.01 (14)	V1—V4—O14—V5^i	171.39 (10)
O7—V1—V5—O9	−172.37 (15)	V3—V4—O14—V5^i	87.90 (7)
O6—V1—V5—O9	−93.46 (14)	O11—V4—O14—V2	−6.7 (5)
O14—V1—V5—O9	−176.26 (14)	O8—V4—O14—V2	88.6 (5)
V3—V1—V5—O9	−175.96 (12)	O13^i—V4—O14—V2	−102.2 (5)
V4—V1—V5—O9	129.01 (12)	O12—V4—O14—V2	177.7 (5)
O1—V1—V5—O5	−8.3 (2)	V2^i—V4—O14—V2	−144.0 (5)
O8—V1—V5—O5	91.37 (16)	V1—V4—O14—V2	81.7 (5)
O7—V1—V5—O5	179.98 (17)	V3—V4—O14—V2	−1.8 (5)
O6—V1—V5—O5	−101.11 (16)	O11—V4—O14—V1	−88.40 (9)
O9—V1—V5—O5	−7.64 (18)	O8—V4—O14—V1	6.92 (8)
O14—V1—V5—O5	176.09 (16)	O13^i—V4—O14—V1	176.05 (8)
V3—V1—V5—O5	176.39 (15)	O12—V4—O14—V1	95.93 (8)
V4—V1—V5—O5	121.36 (15)	V2^i—V4—O14—V1	134.29 (5)
O1—V1—V5—O13	99.81 (14)	V3—V4—O14—V1	−83.49 (6)
O8—V1—V5—O13	−160.52 (9)	O11—V4—O14—V3	−4.91 (8)
O7—V1—V5—O13	−71.90 (11)	O8—V4—O14—V3	90.40 (8)
O6—V1—V5—O13	7.01 (9)	O13^i—V4—O14—V3	−100.46 (8)
O9—V1—V5—O13	100.47 (13)	O12—V4—O14—V3	179.42 (8)
O14—V1—V5—O13	−75.79 (9)	V2^i—V4—O14—V3	−142.23 (5)
V3—V1—V5—O13	−75.49 (7)	V1—V4—O14—V3	83.49 (6)
V4—V1—V5—O13	−130.52 (7)	O7—V3—O14—V5^i	−178.61 (9)
O1—V1—V5—O12	−103.93 (14)	O11—V3—O14—V5^i	−84.68 (9)
O8—V1—V5—O12	−4.26 (9)	O10—V3—O14—V5^i	87.17 (9)
O7—V1—V5—O12	84.36 (11)	O5^i—V3—O14—V5^i	1.03 (8)
O6—V1—V5—O12	163.27 (9)	V1—V3—O14—V5^i	−175.74 (9)
O9—V1—V5—O12	−103.27 (13)	V2—V3—O14—V5^i	90.98 (7)
O14—V1—V5—O12	80.47 (9)	V4—V3—O14—V5^i	−89.36 (7)
V3—V1—V5—O12	80.77 (6)	O7—V3—O14—V2	90.41 (9)
V4—V1—V5—O12	25.74 (6)	O11—V3—O14—V2	−175.66 (9)
O1—V1—V5—O14	175.60 (15)	O10—V3—O14—V2	−3.81 (8)
O8—V1—V5—O14	−84.73 (10)	O5^i—V3—O14—V2	−89.95 (8)
O7—V1—V5—O14	3.89 (11)	V1—V3—O14—V2	93.28 (7)
O6—V1—V5—O14	82.80 (10)	V4—V3—O14—V2	179.66 (9)
O9—V1—V5—O14	176.26 (14)	O7—V3—O14—V1	−2.87 (8)
V3—V1—V5—O14	0.30 (7)	O11—V3—O14—V1	91.06 (8)
V4—V1—V5—O14	−54.73 (7)	O10—V3—O14—V1	−97.09 (9)
O1—V1—V5—O14^i	−179.11 (14)	O5^i—V3—O14—V1	176.77 (9)
O8—V1—V5—O14^i	−79.44 (10)	V2—V3—O14—V1	−93.28 (7)
O7—V1—V5—O14^i	9.18 (12)	V4—V3—O14—V1	86.38 (6)
O6—V1—V5—O14^i	88.09 (10)	O7—V3—O14—V4	−89.25 (9)
O9—V1—V5—O14^i	−178.45 (14)	O11—V3—O14—V4	4.68 (8)
O14—V1—V5—O14^i	5.29 (13)	O10—V3—O14—V4	176.53 (9)
V3—V1—V5—O14^i	5.59 (7)	O5^i—V3—O14—V4	90.39 (8)
V4—V1—V5—O14^i	−49.44 (7)	V1—V3—O14—V4	−86.38 (6)
O9—V5—O5—V3^i	−179.31 (11)	V2—V3—O14—V4	−179.66 (9)
O13—V5—O5—V3^i	78.92 (12)	C6—N1—C2—C3	−54.0 (5)
O12—V5—O5—V3^i	−81.01 (12)	N1—C2—C3—C4	55.4 (5)
O14—V5—O5—V3^i	−4.7 (4)	C2—C3—C4—C5	−56.1 (5)
O14^i—V5—O5—V3^i	−1.50 (11)	C3—C4—C5—C6	56.1 (5)
V1—V5—O5—V3^i	−174.18 (5)	C2—N1—C6—C5	53.4 (5)
O2—V2—O6—C1	29.8 (3)	C4—C5—C6—N1	−55.0 (5)
O10—V2—O6—C1	135.2 (3)	C11—N2—C7—C8	−52.4 (5)
O12^i—V2—O6—C1	−115.0 (3)	N2—C7—C8—C9	54.5 (6)
O13—V2—O6—C1	−68.2 (3)	C7—C8—C9—C10	−57.3 (6)
O14—V2—O6—C1	−142.9 (3)	C8—C9—C10—C11	57.9 (6)
V4^i—V2—O6—C1	−66.3 (3)	C7—N2—C11—C10	51.9 (5)
V3—V2—O6—C1	167.7 (3)	C9—C10—C11—N2	−55.4 (5)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O4^ii	0.90	2.04	2.887 (4)	157
N1—H1E···O12	0.90	1.90	2.774 (4)	162
N2—H2C···O3^iii	0.90	2.53	3.276 (4)	140
N2—H2C···O11^iii	0.90	2.34	3.134 (4)	146
N2—H2D···O8	0.90	1.90	2.795 (4)	174

Symmetry codes: (ii) −x+2, −y, −z+1; (iii) −x+3/2, y+1/2, −z+1/2.