Polymorph of {2-[(2-hydroxy­ethyl)­iminio­methyl]phenolato-[kappa]O}dioxido{2-[(2-oxidoethyl)imino­methyl]phenolato-[kappa]³O,N,O'}molybdenum(VI)

A second polymorphic form (form I) of the previously reported compound {2-[(2-hydroxy­ethyl)­iminio­methyl]­phen­olato-[kappa]O}dioxido{2-[(2-oxido­ethyl)­imino­methyl]­phenolato-[kappa]³O,N,O'}molybdenum(VI) (form II), [Mo(C₉H₉NO₂)O₂(C₉­H₁₁NO₂)], is presented. The title structure differs from the previously reported polymorph [Glowiak, Jerzykiewicz, Sobczak & Ziólkowski (2003). Inorg. Chim. Acta, 356, 387-392] by the fact that the asymmetric unit contains three mol­ecules linked by O-H...O hydrogen bonds. These trimeric units are further linked through O-H...O hydrogen bonds to form a chain parallel to the [11] direction. As in the previous polymorph, each mol­ecule is built up from an MoO₂²⁺ cation surrounded by an O,N,O'-tridentate ligand (O^-C₆H₄­CH=NCH₂CH₂O^-) and weakly coordinated by a second zwitterionic ligand (O^-C₆H₄CH=N⁺HC₂H₄OH). All com­plexes are chiral with the absolute configuration at Mo being C or A. The main difference between the two polymorphs results from the alternation of the chirality at Mo within the chain.

S1. Comment

Molybdenum oxo-complexes bearing polydentate ligands are known to be efficient epoxidation catalysts (Bruno et al., 2006; Herrmann et al., 2002; Martos-Calvente et al., 2004; Most et al., 2002; Valente et al., 2001; Wong et al., 1998; Zhao et al., 2003; Zhou et al., 2004; Sobczak & Ziolkowski, 2003). Thus, since we are interested in investigating the catalytic activity of Mo^VI complexes linked to tridentate ligands, we have synthesized and structurally characterized the title compound, (I), and compare it with the previously published polymorph, (II) (Głowiak et al., 2003).

Reaction of MoO₂(sal)₂ with ethanolamine (HOCH₂CH₂NH₂) under the conditions described by Głowiak et al. (2003) led to a new polymorphic crystalline structure of MoO₂(1,2-OC₆H₄CH═ NC₂H₄O)(1,2-O^-C₆H₄CH═N⁺HC₂H₄OH) with three crystallographically independent molecules per unit cell. The two polymorphs crystallize in triclinic space group P1 with different cell parameters [for (I), a = 10.096 Å, b = 13.565 Å, c = 21.879 Å, α = 81.68°, β = 86.40°, γ = 71.41°, V = 2810.9 ų and Z = 6; for (II), a = 8.483 Å, b = 10.187 Å, c = 11.034 Å, α = 105.26°, β = 95.29°, γ = 95.10°, V = 909.6 ų and Z = 2].

For both (I) and (II), the molecule is based on an MoO₂²⁺ cation surrounded by a doubly charged anionic ONO tridentate ligand (O^-C₆H₄CH═ NCH₂CH₂O^-) and weakly O-coordinated to a zwitterionic ligand (O^-C₆H₄CH═N⁺HC₂H₄OH) (Fig. 1). The zwitterionic form is stabilized by intramolecular N—H···O hydrogen bonds between the N⁺H group and the O atom within the same ligand linked to the Mo. A second weak interaction may be noted between the same N⁺H group and one of the O atoms of the tridentate ligand (O13, O23 or O33; Table 1).

All the crystallographically independent complexes are chiral at Mo, and the absolute configuration of each Mo could be determined as either C (clockwise) or A (anticlockwise) (Fig. 2) using the official nomenclature rules for such compounds (Brown et al., 1975; Hartung et al., 2006).

The title polymorph structure (I) differs from structure (II) by the fact that the asymmetric unit of (I) contains three molecules linked by O—H···O hydrogen bonds (Table 1) involving the hydroxyl O atom of the zwitterionic ligand of one molecule to an oxo O atom attached to the Mo atom of another molecule. These trimeric units are further linked through O—H···O hydrogen bonds of the same type to form a chain parallel to the [111] direction (Fig. 3).

Although the chirality is different for each molecule, they have roughly the same conformation. Indeed, an overlay analysis calculated using structure matching software (Watkin et al., 2003; Collins et al., 2006) shows that the three molecules can be superimposed (Fig. 4, Table 2). A similar overlay analysis of the two polymorphs indicates that the largest deviation occurs for the dangling hydroxyl O atom (Fig. 4) not coordinated to the Mo atom and involved in hydrogen bonding, which is not surprising owing to the different packing observed in the two isomers. However, it is worth pointing out that in compound (II), the chain is formed from complexes having the same configuration C (or A), whereas in compound (I), the chain is built up from trimeric units linked by translation to form infinite (CAC)_n [or (ACA)_n] chains (Fig. 2).

As observed in polymorph (II), there are also intramolecular hydrogen bonds between the dangling NH (N12, N22 or N32) group of the monodentate ligand and the O atom (O15, O25 or O35) within the same ligand. Moreover, the position of the dangling CH₂NHCH₂CH₂OH chain over the chelating ligand is certainly induced by a second weak N—H···O interaction involving one of the O atoms (O13, O23 or O33) of the tridentate ligand (Table 1).

Related literature

For related literature, see: Brown et al. (1975); Bruno et al. (2006); Collins et al. (2006); Głowiak et al. (2003); Hartung et al. (2006); Herrmann et al. (2002); Martos-Calvente, De La Pena O'Shea, Campos-Martin, Fierro & Gutierrez-Puebla (2004); Most et al. (2002); Sobczak & Ziolkowski (2003); Spek (2003); Valente et al. (2001); Watkin et al. (2003); Wong et al. (1998); Yamanouchi & Yamada (1974); Zhao et al. (2003); Zhou et al. (2004).

S2. Experimental

Less than two equivalents of HOCH₂CH₂NH₂ (0.3 ml, 4.97 mmol) were added to an ethanol solution (10 ml) of one equivalent of MoO₂(sal)₂ (0.92 g, 2.48 mmol), previously synthesized following a literature procedure (Yamanouchi & Yamada, 1974). The mixture was maintained under reflux for 30 min. The white precipitate that formed was separated off. The solution was subsequently cooled to room temperature and left to stand in air. Evaporation of the filtrate gave air-stable yellow crystals of the title compound, (I). The IR spectrum of the yellow crystals in KBr pellets showed no visible difference with the compound synthesized previously (Głowiak et al., 2003)

S3. Refinement

All H atoms were fixed geometrically and treated as riding, with C—H = 0.93 Å (aromatic) or 0.97 Å (methylene), O—H = 0.84 Å and N—H = 0.88 Å, with U_iso(H) = 1.2U_eq(C), 1.5U_eq(C) or 1.2U_eq(N). [Please check revised text, which has been amended to include N-bound H-atom treatment]

The two polymorphs have the same space group P1 but no relation between them could be found. Moreover, the simulated powder patterns produced using PLATON (Spek, 2003) are different (Fig. 5).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997), CAMERON (Pearce et al., 2000) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The asymmetric unit of (I), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity.
	Fig. 2. Scheme showing the two enantiomers, C and A, with the priority numbers used to define the absolute configuration shown as subscripted indices.
	Fig. 3. A partial packing view of compound (I), showing the formation of chains along [111] built from hydrogen bonds. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted.
	Fig. 4. Overlays of the different molecules within the title compound, A, B and C, and an overlay of the two polymorphs, D.
	Fig. 5. A view of the simulated powder patterns for polymorphs (I) (top?) and (II) (bottom?).

{2-[(2-hydroxyethyl)iminiomethyl]phenolato-κO}dioxido(2-[(2-oxidoethyl)iminomethyl]phenolato-κ³O,N,O')molybdenum(VI)

Crystal data

[Mo(C9H9NO2)O2(C9H11NO2)]	Z = 6
Mr = 456.30	F(000) = 1392
Triclinic, P1	Dx = 1.617 Mg m^−3
a = 10.0953 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.5645 (8) Å	Cell parameters from 15657 reflections
c = 21.8864 (14) Å	θ = 2.8–31.9°
α = 81.731 (5)°	µ = 0.74 mm^−1
β = 86.437 (5)°	T = 180 K
γ = 71.422 (5)°	Box, pale yellow
V = 2810.9 (3) Å^3	0.76 × 0.33 × 0.27 mm

Data collection

Oxford Diffraction Xcalibur diffractometer	13842 independent reflections
Radiation source: fine-focus sealed tube	10817 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.2632 pixels mm^-1	θmax = 28.3°, θmin = 2.8°
ω and ϕ scans	h = −12→13
Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction, 2007); empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm]	k = −15→18
Tmin = 0.762, Tmax = 0.834	l = −26→29
24992 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0361P)^2 + 4.7867P] where P = (Fo^2 + 2Fc^2)/3
13844 reflections	(Δ/σ)max = 0.004
733 parameters	Δρmax = 1.02 e Å^−3
0 restraints	Δρmin = −1.10 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
Mo1	0.71809 (3)	0.19222 (2)	0.475213 (12)	0.01746 (7)
N11	0.5452 (3)	0.3365 (2)	0.43393 (14)	0.0260 (6)
N12	0.5260 (3)	0.2633 (2)	0.64495 (14)	0.0254 (6)
H12	0.5503	0.2508	0.6068	0.031*
O11	0.8554 (3)	0.1098 (2)	0.51756 (11)	0.0303 (6)
O12	0.7026 (3)	0.1273 (2)	0.41596 (11)	0.0288 (6)
O13	0.5537 (2)	0.16546 (18)	0.52010 (10)	0.0212 (5)
O14	0.8136 (2)	0.28157 (19)	0.42987 (11)	0.0233 (5)
O15	0.6753 (3)	0.2953 (2)	0.54756 (12)	0.0329 (6)
O16	0.2490 (3)	0.4049 (2)	0.64413 (13)	0.0364 (7)
H1	0.2289	0.4194	0.6803	0.055*
C11	0.4164 (4)	0.3460 (3)	0.43072 (17)	0.0293 (8)
H11	0.3571	0.4087	0.4090	0.035*
C12	0.3551 (3)	0.2671 (3)	0.45820 (16)	0.0236 (7)
C13	0.2169 (4)	0.2794 (3)	0.44314 (18)	0.0310 (8)
H13	0.1678	0.3396	0.4161	0.037*
C14	0.1492 (4)	0.2069 (3)	0.46633 (18)	0.0324 (9)
H14	0.0561	0.2163	0.4551	0.039*
C15	0.2224 (4)	0.1203 (3)	0.50650 (17)	0.0265 (7)
H15	0.1788	0.0692	0.5225	0.032*
C16	0.3572 (3)	0.1065 (3)	0.52369 (15)	0.0225 (7)
H16	0.4045	0.0470	0.5516	0.027*
C17	0.4244 (3)	0.1803 (3)	0.50001 (15)	0.0198 (6)
C18	0.6036 (4)	0.4172 (3)	0.4035 (2)	0.0452 (11)
H18A	0.6113	0.4639	0.4331	0.054*
H18B	0.5447	0.4601	0.3688	0.054*
C19	0.7468 (4)	0.3561 (3)	0.3805 (2)	0.0372 (9)
H19A	0.7376	0.3205	0.3453	0.045*
H19B	0.8020	0.4041	0.3665	0.045*
C151	0.7445 (3)	0.3347 (3)	0.57998 (16)	0.0221 (7)
C152	0.8559 (4)	0.3709 (3)	0.55523 (17)	0.0276 (8)
H152	0.8839	0.3649	0.5133	0.033*
C153	0.9240 (4)	0.4144 (3)	0.59054 (18)	0.0287 (8)
H153	0.9990	0.4377	0.5730	0.034*
C154	0.8838 (4)	0.4250 (3)	0.65295 (18)	0.0319 (8)
H154	0.9311	0.4556	0.6772	0.038*
C155	0.7763 (4)	0.3909 (3)	0.67812 (17)	0.0297 (8)
H155	0.7492	0.3980	0.7200	0.036*
C156	0.7051 (3)	0.3453 (3)	0.64296 (16)	0.0223 (7)
C157	0.5952 (4)	0.3095 (3)	0.67180 (16)	0.0248 (7)
H157	0.5715	0.3204	0.7135	0.030*
C158	0.4103 (4)	0.2304 (3)	0.67364 (18)	0.0312 (8)
H15A	0.4048	0.2371	0.7183	0.037*
H15B	0.4262	0.1559	0.6692	0.037*
C159	0.2741 (4)	0.2975 (3)	0.64349 (17)	0.0275 (8)
H15C	0.2761	0.2837	0.6002	0.033*
H15D	0.1961	0.2770	0.6653	0.033*
Mo2	0.01883 (3)	0.53892 (2)	0.809053 (13)	0.01874 (7)
N21	0.0744 (3)	0.6883 (2)	0.77954 (13)	0.0235 (6)
N22	0.0970 (3)	0.5974 (2)	0.98532 (13)	0.0260 (6)
H22	0.0945	0.5842	0.9473	0.031*
O21	−0.0617 (3)	0.4533 (2)	0.84618 (12)	0.0312 (6)
O22	0.1074 (3)	0.4814 (2)	0.74740 (11)	0.0307 (6)
O23	0.1930 (2)	0.50697 (19)	0.85537 (10)	0.0232 (5)
O24	−0.1414 (2)	0.6334 (2)	0.76566 (11)	0.0269 (5)
O25	−0.0497 (2)	0.6286 (2)	0.88798 (11)	0.0271 (5)
O26	0.2359 (3)	0.7519 (2)	0.97421 (13)	0.0411 (7)
H2	0.2352	0.7700	1.0094	0.062*
C21	0.1957 (4)	0.6992 (3)	0.77746 (16)	0.0254 (7)
H21	0.2045	0.7658	0.7614	0.030*
C22	0.3198 (4)	0.6158 (3)	0.79830 (16)	0.0226 (7)
C23	0.4504 (4)	0.6287 (3)	0.78206 (18)	0.0298 (8)
H23	0.4540	0.6918	0.7578	0.036*
C24	0.5748 (4)	0.5519 (3)	0.80037 (19)	0.0322 (8)
H24	0.6625	0.5617	0.7888	0.039*
C25	0.5676 (4)	0.4606 (3)	0.83587 (18)	0.0317 (8)
H25	0.6516	0.4069	0.8483	0.038*
C26	0.4408 (4)	0.4461 (3)	0.85348 (17)	0.0283 (8)
H26	0.4389	0.3833	0.8785	0.034*
C27	0.3144 (3)	0.5228 (3)	0.83497 (15)	0.0213 (7)
C28	−0.0473 (4)	0.7740 (3)	0.7553 (2)	0.0379 (10)
H28A	−0.0184	0.8257	0.7254	0.046*
H28B	−0.1027	0.8102	0.7892	0.046*
C29	−0.1300 (4)	0.7212 (3)	0.72414 (19)	0.0375 (9)
H29A	−0.2240	0.7707	0.7138	0.045*
H29B	−0.0819	0.6979	0.6855	0.045*
C251	−0.1637 (4)	0.6622 (3)	0.92073 (15)	0.0201 (6)
C252	−0.2977 (4)	0.6989 (3)	0.89577 (16)	0.0249 (7)
H252	−0.3080	0.6979	0.8530	0.030*
C253	−0.4152 (4)	0.7365 (3)	0.93184 (18)	0.0315 (8)
H253	−0.5048	0.7608	0.9137	0.038*
C254	−0.4038 (4)	0.7394 (3)	0.99515 (18)	0.0335 (9)
H254	−0.4850	0.7652	1.0198	0.040*
C255	−0.2743 (4)	0.7046 (3)	1.02084 (16)	0.0293 (8)
H255	−0.2661	0.7064	1.0636	0.035*
C256	−0.1531 (4)	0.6661 (3)	0.98503 (15)	0.0209 (7)
C257	−0.0207 (4)	0.6349 (3)	1.01292 (16)	0.0258 (7)
H257	−0.0188	0.6423	1.0553	0.031*
C258	0.2334 (4)	0.5749 (3)	1.01142 (18)	0.0319 (8)
H25A	0.2880	0.5004	1.0096	0.038*
H25B	0.2228	0.5868	1.0553	0.038*
C259	0.3101 (4)	0.6446 (3)	0.97604 (18)	0.0338 (9)
H25C	0.4016	0.6300	0.9954	0.041*
H25D	0.3282	0.6272	0.9333	0.041*
Mo3	0.29709 (3)	0.85939 (2)	1.145206 (13)	0.02017 (7)
N31	0.1199 (3)	0.9983 (2)	1.10182 (14)	0.0278 (7)
N32	0.1088 (3)	0.9258 (2)	1.31410 (13)	0.0248 (6)
H32	0.1306	0.9153	1.2755	0.030*
O31	0.4360 (3)	0.7835 (2)	1.18894 (11)	0.0287 (5)
O32	0.2880 (3)	0.7881 (2)	1.08792 (12)	0.0340 (6)
O33	0.1351 (2)	0.82979 (18)	1.19075 (10)	0.0218 (5)
O34	0.3888 (3)	0.9492 (2)	1.09707 (11)	0.0309 (6)
O35	0.2487 (2)	0.96756 (19)	1.21485 (11)	0.0236 (5)
O36	−0.1670 (3)	1.0694 (2)	1.30853 (12)	0.0318 (6)
H3	−0.1968	1.0878	1.3432	0.048*
C31	−0.0107 (4)	1.0097 (3)	1.10216 (17)	0.0303 (8)
H31	−0.0716	1.0728	1.0815	0.036*
C32	−0.0713 (4)	0.9304 (3)	1.13274 (16)	0.0263 (7)
C33	−0.2108 (4)	0.9420 (3)	1.12042 (19)	0.0352 (9)
H33	−0.2643	1.0025	1.0948	0.042*
C34	−0.2702 (4)	0.8674 (4)	1.1449 (2)	0.0405 (10)
H34	−0.3649	0.8766	1.1365	0.049*
C35	−0.1939 (4)	0.7788 (3)	1.18182 (18)	0.0331 (9)
H35	−0.2348	0.7258	1.1973	0.040*
C36	−0.0578 (4)	0.7669 (3)	1.19635 (17)	0.0268 (7)
H36	−0.0068	0.7067	1.2229	0.032*
C37	0.0056 (3)	0.8423 (3)	1.17235 (15)	0.0209 (7)
C38	0.1751 (5)	1.0778 (3)	1.0679 (2)	0.0458 (11)
H38A	0.1811	1.1285	1.0952	0.055*
H38B	0.1151	1.1165	1.0326	0.055*
C39	0.3194 (5)	1.0170 (4)	1.0457 (2)	0.0466 (11)
H39A	0.3117	0.9761	1.0128	0.056*
H39B	0.3717	1.0657	1.0288	0.056*
C351	0.3250 (3)	1.0002 (2)	1.24838 (15)	0.0185 (6)
C352	0.4348 (4)	1.0372 (3)	1.22344 (16)	0.0255 (7)
H352	0.4584	1.0369	1.1808	0.031*
C353	0.5077 (4)	1.0737 (3)	1.26071 (17)	0.0284 (8)
H353	0.5815	1.0983	1.2430	0.034*
C354	0.4780 (4)	1.0762 (3)	1.32357 (18)	0.0300 (8)
H354	0.5307	1.1017	1.3483	0.036*
C355	0.3712 (4)	1.0410 (3)	1.34896 (16)	0.0254 (7)
H355	0.3490	1.0431	1.3917	0.030*
C356	0.2940 (3)	1.0019 (3)	1.31282 (15)	0.0204 (6)
C357	0.1830 (4)	0.9670 (3)	1.34139 (16)	0.0238 (7)
H357	0.1626	0.9747	1.3837	0.029*
C358	−0.0091 (4)	0.8953 (3)	1.34268 (17)	0.0288 (8)
H35A	−0.0170	0.9051	1.3869	0.035*
H35B	0.0066	0.8202	1.3400	0.035*
C359	−0.1432 (4)	0.9608 (3)	1.31059 (17)	0.0263 (7)
H35C	−0.1392	0.9437	1.2679	0.032*
H35D	−0.2226	0.9424	1.3325	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mo1	0.01563 (13)	0.02193 (14)	0.01543 (13)	−0.00617 (11)	−0.00184 (10)	−0.00307 (10)
N11	0.0202 (15)	0.0218 (15)	0.0330 (16)	−0.0050 (12)	0.0009 (12)	0.0011 (12)
N12	0.0212 (15)	0.0293 (16)	0.0239 (15)	−0.0061 (12)	0.0018 (12)	−0.0022 (12)
O11	0.0195 (12)	0.0398 (15)	0.0281 (13)	−0.0078 (11)	−0.0074 (10)	0.0066 (11)
O12	0.0337 (14)	0.0322 (14)	0.0241 (13)	−0.0118 (11)	−0.0015 (10)	−0.0117 (10)
O13	0.0170 (11)	0.0274 (12)	0.0205 (11)	−0.0097 (10)	−0.0036 (9)	−0.0004 (9)
O14	0.0187 (12)	0.0263 (13)	0.0248 (12)	−0.0082 (10)	0.0005 (9)	−0.0004 (10)
O15	0.0304 (14)	0.0515 (17)	0.0305 (14)	−0.0258 (13)	0.0093 (11)	−0.0241 (12)
O16	0.0403 (16)	0.0247 (13)	0.0407 (16)	−0.0073 (12)	0.0181 (13)	−0.0082 (12)
C11	0.0236 (18)	0.0230 (18)	0.036 (2)	−0.0016 (14)	−0.0033 (15)	0.0034 (15)
C12	0.0157 (16)	0.0250 (17)	0.0296 (18)	−0.0048 (13)	0.0017 (13)	−0.0068 (14)
C13	0.0177 (17)	0.031 (2)	0.039 (2)	−0.0006 (15)	−0.0048 (15)	−0.0017 (16)
C14	0.0147 (17)	0.041 (2)	0.043 (2)	−0.0061 (15)	−0.0047 (15)	−0.0149 (18)
C15	0.0198 (17)	0.0330 (19)	0.0329 (19)	−0.0148 (15)	0.0051 (14)	−0.0116 (15)
C16	0.0207 (16)	0.0260 (17)	0.0230 (17)	−0.0095 (14)	0.0031 (13)	−0.0072 (13)
C17	0.0169 (15)	0.0235 (16)	0.0234 (16)	−0.0107 (13)	0.0069 (12)	−0.0109 (13)
C18	0.028 (2)	0.025 (2)	0.073 (3)	−0.0043 (16)	0.004 (2)	0.015 (2)
C19	0.029 (2)	0.035 (2)	0.042 (2)	−0.0111 (17)	0.0033 (17)	0.0133 (17)
C151	0.0189 (16)	0.0227 (17)	0.0268 (17)	−0.0065 (13)	−0.0014 (13)	−0.0093 (13)
C152	0.0267 (18)	0.034 (2)	0.0290 (18)	−0.0149 (16)	0.0034 (15)	−0.0152 (15)
C153	0.0187 (17)	0.0259 (18)	0.046 (2)	−0.0116 (14)	−0.0084 (15)	−0.0056 (16)
C154	0.034 (2)	0.032 (2)	0.034 (2)	−0.0113 (16)	−0.0154 (16)	−0.0081 (16)
C155	0.033 (2)	0.0306 (19)	0.0236 (18)	−0.0046 (16)	−0.0056 (15)	−0.0085 (15)
C156	0.0205 (16)	0.0183 (16)	0.0252 (17)	−0.0008 (13)	−0.0045 (13)	−0.0036 (13)
C157	0.0227 (17)	0.0255 (18)	0.0216 (17)	−0.0022 (14)	−0.0016 (13)	−0.0004 (13)
C158	0.0287 (19)	0.030 (2)	0.033 (2)	−0.0105 (16)	0.0064 (15)	0.0026 (15)
C159	0.0203 (17)	0.0293 (19)	0.0322 (19)	−0.0059 (14)	0.0060 (14)	−0.0090 (15)
Mo2	0.02038 (14)	0.02072 (14)	0.01609 (13)	−0.00746 (11)	−0.00021 (10)	−0.00332 (10)
N21	0.0202 (14)	0.0229 (15)	0.0250 (15)	−0.0047 (12)	0.0005 (11)	−0.0003 (11)
N22	0.0305 (16)	0.0285 (16)	0.0220 (15)	−0.0139 (13)	−0.0039 (12)	−0.0009 (12)
O21	0.0305 (14)	0.0331 (14)	0.0328 (14)	−0.0162 (12)	0.0002 (11)	−0.0002 (11)
O22	0.0339 (15)	0.0337 (14)	0.0251 (13)	−0.0094 (12)	0.0038 (11)	−0.0100 (11)
O23	0.0204 (12)	0.0261 (12)	0.0201 (12)	−0.0053 (10)	−0.0011 (9)	0.0026 (9)
O24	0.0213 (12)	0.0329 (14)	0.0257 (13)	−0.0075 (11)	−0.0052 (10)	−0.0013 (10)
O25	0.0207 (12)	0.0405 (15)	0.0212 (12)	−0.0074 (11)	0.0033 (10)	−0.0139 (11)
O26	0.063 (2)	0.0342 (16)	0.0326 (15)	−0.0223 (15)	−0.0184 (14)	−0.0010 (12)
C21	0.0266 (18)	0.0202 (17)	0.0291 (18)	−0.0080 (14)	0.0003 (14)	−0.0015 (14)
C22	0.0197 (16)	0.0233 (17)	0.0247 (17)	−0.0056 (13)	−0.0003 (13)	−0.0059 (13)
C23	0.0258 (19)	0.0269 (19)	0.039 (2)	−0.0111 (15)	−0.0011 (16)	−0.0036 (16)
C24	0.0187 (18)	0.038 (2)	0.046 (2)	−0.0145 (16)	0.0039 (16)	−0.0156 (18)
C25	0.0241 (18)	0.030 (2)	0.039 (2)	−0.0032 (15)	−0.0030 (16)	−0.0111 (16)
C26	0.0266 (19)	0.0265 (18)	0.0301 (19)	−0.0057 (15)	−0.0037 (15)	−0.0026 (15)
C27	0.0202 (16)	0.0254 (17)	0.0199 (16)	−0.0081 (13)	0.0013 (12)	−0.0068 (13)
C28	0.028 (2)	0.0234 (19)	0.056 (3)	−0.0040 (16)	−0.0066 (18)	0.0089 (17)
C29	0.032 (2)	0.039 (2)	0.036 (2)	−0.0079 (18)	−0.0082 (17)	0.0084 (17)
C251	0.0241 (17)	0.0188 (16)	0.0197 (16)	−0.0095 (13)	0.0029 (13)	−0.0054 (12)
C252	0.0229 (17)	0.0286 (18)	0.0253 (17)	−0.0101 (14)	0.0013 (14)	−0.0060 (14)
C253	0.0228 (18)	0.036 (2)	0.036 (2)	−0.0108 (16)	0.0057 (15)	−0.0039 (16)
C254	0.030 (2)	0.033 (2)	0.038 (2)	−0.0105 (16)	0.0162 (17)	−0.0120 (17)
C255	0.041 (2)	0.0304 (19)	0.0211 (17)	−0.0168 (17)	0.0071 (15)	−0.0066 (14)
C256	0.0275 (18)	0.0197 (16)	0.0186 (16)	−0.0115 (14)	0.0016 (13)	−0.0036 (12)
C257	0.038 (2)	0.0227 (17)	0.0210 (17)	−0.0167 (15)	−0.0011 (15)	−0.0004 (13)
C258	0.0285 (19)	0.034 (2)	0.036 (2)	−0.0129 (16)	−0.0104 (16)	0.0000 (16)
C259	0.041 (2)	0.039 (2)	0.031 (2)	−0.0233 (19)	−0.0015 (17)	−0.0090 (17)
Mo3	0.02375 (15)	0.02210 (15)	0.01581 (14)	−0.00820 (12)	−0.00104 (11)	−0.00358 (10)
N31	0.0316 (17)	0.0255 (16)	0.0284 (16)	−0.0138 (13)	−0.0099 (13)	0.0053 (12)
N32	0.0208 (14)	0.0286 (16)	0.0235 (15)	−0.0068 (12)	0.0012 (11)	−0.0012 (12)
O31	0.0223 (13)	0.0344 (14)	0.0268 (13)	−0.0053 (11)	−0.0026 (10)	−0.0034 (11)
O32	0.0429 (16)	0.0366 (15)	0.0266 (14)	−0.0148 (13)	−0.0008 (12)	−0.0117 (11)
O33	0.0220 (12)	0.0241 (12)	0.0217 (12)	−0.0110 (10)	−0.0040 (9)	0.0001 (9)
O34	0.0361 (15)	0.0411 (15)	0.0222 (12)	−0.0233 (13)	0.0000 (11)	−0.0002 (11)
O35	0.0241 (12)	0.0306 (13)	0.0223 (12)	−0.0144 (10)	−0.0001 (9)	−0.0106 (10)
O36	0.0334 (15)	0.0239 (13)	0.0348 (15)	−0.0066 (11)	0.0088 (12)	−0.0031 (11)
C31	0.034 (2)	0.0241 (18)	0.0301 (19)	−0.0056 (15)	−0.0121 (16)	0.0031 (15)
C32	0.0211 (17)	0.0322 (19)	0.0241 (18)	−0.0040 (15)	−0.0046 (14)	−0.0074 (14)
C33	0.0244 (19)	0.041 (2)	0.036 (2)	−0.0018 (17)	−0.0104 (16)	−0.0091 (17)
C34	0.027 (2)	0.055 (3)	0.044 (2)	−0.0123 (19)	0.0011 (17)	−0.023 (2)
C35	0.030 (2)	0.042 (2)	0.037 (2)	−0.0201 (18)	0.0080 (16)	−0.0183 (18)
C36	0.0274 (18)	0.0269 (18)	0.0291 (18)	−0.0113 (15)	0.0021 (14)	−0.0078 (14)
C37	0.0212 (16)	0.0249 (17)	0.0196 (16)	−0.0081 (13)	−0.0008 (12)	−0.0106 (13)
C38	0.055 (3)	0.032 (2)	0.051 (3)	−0.023 (2)	−0.018 (2)	0.0179 (19)
C39	0.061 (3)	0.051 (3)	0.033 (2)	−0.033 (2)	−0.005 (2)	0.0150 (19)
C351	0.0180 (15)	0.0142 (15)	0.0220 (16)	−0.0017 (12)	−0.0028 (12)	−0.0048 (12)
C352	0.0249 (18)	0.0270 (18)	0.0259 (18)	−0.0091 (14)	0.0011 (14)	−0.0063 (14)
C353	0.0213 (17)	0.0297 (19)	0.035 (2)	−0.0086 (15)	−0.0027 (15)	−0.0035 (15)
C354	0.0280 (19)	0.0292 (19)	0.035 (2)	−0.0068 (15)	−0.0125 (15)	−0.0103 (16)
C355	0.0218 (17)	0.0298 (19)	0.0217 (17)	−0.0016 (14)	−0.0072 (13)	−0.0068 (14)
C356	0.0187 (16)	0.0207 (16)	0.0207 (16)	−0.0034 (13)	−0.0037 (12)	−0.0044 (12)
C357	0.0236 (17)	0.0228 (17)	0.0202 (16)	−0.0008 (14)	−0.0015 (13)	−0.0011 (13)
C358	0.0220 (17)	0.0306 (19)	0.033 (2)	−0.0096 (15)	0.0022 (15)	0.0019 (15)
C359	0.0217 (17)	0.0276 (18)	0.0287 (18)	−0.0059 (14)	0.0023 (14)	−0.0065 (14)

Geometric parameters (Å, º)

Mo1—O11	1.704 (2)	C25—H25	0.9500
Mo1—O12	1.710 (2)	C26—C27	1.404 (5)
Mo1—O14	1.914 (2)	C26—H26	0.9500
Mo1—O13	1.982 (2)	C28—C29	1.506 (6)
Mo1—O15	2.194 (2)	C28—H28A	0.9900
Mo1—N11	2.281 (3)	C28—H28B	0.9900
N11—C11	1.270 (4)	C29—H29A	0.9900
N11—C18	1.463 (5)	C29—H29B	0.9900
N12—C157	1.290 (5)	C251—C252	1.400 (5)
N12—C158	1.455 (4)	C251—C256	1.428 (4)
N12—H12	0.8800	C252—C253	1.380 (5)
O13—C17	1.347 (4)	C252—H252	0.9500
O14—C19	1.410 (4)	C253—C254	1.405 (5)
O15—C151	1.299 (4)	C253—H253	0.9500
O16—C159	1.399 (4)	C254—C255	1.368 (6)
O16—H1	0.8400	C254—H254	0.9500
C11—C12	1.443 (5)	C255—C256	1.405 (5)
C11—H11	0.9500	C255—H255	0.9500
C12—C17	1.400 (5)	C256—C257	1.416 (5)
C12—C13	1.406 (5)	C257—H257	0.9500
C13—C14	1.390 (5)	C258—C259	1.508 (5)
C13—H13	0.9500	C258—H25A	0.9900
C14—C15	1.390 (5)	C258—H25B	0.9900
C14—H14	0.9500	C259—H25C	0.9900
C15—C16	1.382 (5)	C259—H25D	0.9900
C15—H15	0.9500	Mo3—O31	1.705 (2)
C16—C17	1.403 (4)	Mo3—O32	1.713 (2)
C16—H16	0.9500	Mo3—O34	1.918 (2)
C18—C19	1.515 (6)	Mo3—O33	1.982 (2)
C18—H18A	0.9900	Mo3—O35	2.193 (2)
C18—H18B	0.9900	Mo3—N31	2.281 (3)
C19—H19A	0.9900	N31—C31	1.278 (5)
C19—H19B	0.9900	N31—C38	1.458 (5)
C151—C152	1.414 (5)	N32—C357	1.284 (5)
C151—C156	1.425 (5)	N32—C358	1.458 (4)
C152—C153	1.369 (5)	N32—H32	0.8800
C152—H152	0.9500	O33—C37	1.343 (4)
C153—C154	1.415 (5)	O34—C39	1.411 (5)
C153—H153	0.9500	O35—C351	1.307 (4)
C154—C155	1.367 (5)	O36—C359	1.409 (4)
C154—H154	0.9500	O36—H3	0.8400
C155—C156	1.407 (5)	C31—C32	1.463 (5)
C155—H155	0.9500	C31—H31	0.9500
C156—C157	1.425 (5)	C32—C33	1.405 (5)
C157—H157	0.9500	C32—C37	1.406 (5)
C158—C159	1.516 (5)	C33—C34	1.365 (6)
C158—H15A	0.9900	C33—H33	0.9500
C158—H15B	0.9900	C34—C35	1.377 (6)
C159—H15C	0.9900	C34—H34	0.9500
C159—H15D	0.9900	C35—C36	1.383 (5)
Mo2—O21	1.709 (2)	C35—H35	0.9500
Mo2—O22	1.714 (2)	C36—C37	1.398 (5)
Mo2—O24	1.919 (2)	C36—H36	0.9500
Mo2—O23	1.979 (2)	C38—C39	1.516 (7)
Mo2—O25	2.205 (2)	C38—H38A	0.9900
Mo2—N21	2.267 (3)	C38—H38B	0.9900
N21—C21	1.277 (4)	C39—H39A	0.9900
N21—C28	1.460 (5)	C39—H39B	0.9900
N22—C257	1.285 (5)	C351—C352	1.408 (5)
N22—C258	1.448 (5)	C351—C356	1.427 (4)
N22—H22	0.8800	C352—C353	1.369 (5)
O23—C27	1.349 (4)	C352—H352	0.9500
O24—C29	1.422 (5)	C353—C354	1.393 (5)
O25—C251	1.305 (4)	C353—H353	0.9500
O26—C259	1.405 (5)	C354—C355	1.370 (5)
O26—H2	0.8400	C354—H354	0.9500
C21—C22	1.442 (5)	C355—C356	1.405 (5)
C21—H21	0.9500	C355—H355	0.9500
C22—C23	1.402 (5)	C356—C357	1.427 (5)
C22—C27	1.409 (5)	C357—H357	0.9500
C23—C24	1.390 (5)	C358—C359	1.512 (5)
C23—H23	0.9500	C358—H35A	0.9900
C24—C25	1.384 (6)	C358—H35B	0.9900
C24—H24	0.9500	C359—H35C	0.9900
C25—C26	1.379 (5)	C359—H35D	0.9900
O11—Mo1—O12	105.87 (13)	N21—C28—C29	104.4 (3)
O11—Mo1—O14	98.02 (11)	N21—C28—H28A	110.9
O12—Mo1—O14	97.57 (11)	C29—C28—H28A	110.9
O11—Mo1—O13	103.18 (11)	N21—C28—H28B	110.9
O12—Mo1—O13	92.42 (11)	C29—C28—H28B	110.9
O14—Mo1—O13	153.09 (10)	H28A—C28—H28B	108.9
O11—Mo1—O15	88.17 (12)	O24—C29—C28	107.8 (3)
O12—Mo1—O15	164.04 (11)	O24—C29—H29A	110.2
O14—Mo1—O15	87.72 (10)	C28—C29—H29A	110.2
O13—Mo1—O15	76.69 (9)	O24—C29—H29B	110.2
O11—Mo1—N11	163.69 (12)	C28—C29—H29B	110.2
O12—Mo1—N11	89.81 (12)	H29A—C29—H29B	108.5
O14—Mo1—N11	75.01 (10)	O25—C251—C252	123.5 (3)
O13—Mo1—N11	80.12 (10)	O25—C251—C256	119.1 (3)
O15—Mo1—N11	76.97 (11)	C252—C251—C256	117.3 (3)
C11—N11—C18	121.8 (3)	C253—C252—C251	121.5 (3)
C11—N11—Mo1	127.1 (2)	C253—C252—H252	119.2
C18—N11—Mo1	110.8 (2)	C251—C252—H252	119.2
C157—N12—C158	124.2 (3)	C252—C253—C254	120.7 (4)
C157—N12—H12	117.9	C252—C253—H253	119.6
C158—N12—H12	117.9	C254—C253—H253	119.6
C17—O13—Mo1	130.2 (2)	C255—C254—C253	119.2 (3)
C19—O14—Mo1	119.8 (2)	C255—C254—H254	120.4
C151—O15—Mo1	138.1 (2)	C253—C254—H254	120.4
C159—O16—H1	109.5	C254—C255—C256	121.1 (3)
N11—C11—C12	123.7 (3)	C254—C255—H255	119.4
N11—C11—H11	118.1	C256—C255—H255	119.4
C12—C11—H11	118.1	C255—C256—C257	119.3 (3)
C17—C12—C13	118.2 (3)	C255—C256—C251	120.1 (3)
C17—C12—C11	123.7 (3)	C257—C256—C251	120.6 (3)
C13—C12—C11	118.1 (3)	N22—C257—C256	125.1 (3)
C14—C13—C12	122.6 (3)	N22—C257—H257	117.5
C14—C13—H13	118.7	C256—C257—H257	117.5
C12—C13—H13	118.7	N22—C258—C259	110.0 (3)
C13—C14—C15	117.7 (3)	N22—C258—H25A	109.7
C13—C14—H14	121.2	C259—C258—H25A	109.7
C15—C14—H14	121.2	N22—C258—H25B	109.7
C16—C15—C14	121.6 (3)	C259—C258—H25B	109.7
C16—C15—H15	119.2	H25A—C258—H25B	108.2
C14—C15—H15	119.2	O26—C259—C258	113.0 (3)
C15—C16—C17	120.2 (3)	O26—C259—H25C	109.0
C15—C16—H16	119.9	C258—C259—H25C	109.0
C17—C16—H16	119.9	O26—C259—H25D	109.0
O13—C17—C12	122.4 (3)	C258—C259—H25D	109.0
O13—C17—C16	117.9 (3)	H25C—C259—H25D	107.8
C12—C17—C16	119.7 (3)	O31—Mo3—O32	105.83 (13)
N11—C18—C19	104.4 (3)	O31—Mo3—O34	97.69 (12)
N11—C18—H18A	110.9	O32—Mo3—O34	97.01 (12)
C19—C18—H18A	110.9	O31—Mo3—O33	103.37 (11)
N11—C18—H18B	110.9	O32—Mo3—O33	92.38 (12)
C19—C18—H18B	110.9	O34—Mo3—O33	153.62 (11)
H18A—C18—H18B	108.9	O31—Mo3—O35	87.58 (11)
O14—C19—C18	107.6 (3)	O32—Mo3—O35	164.75 (11)
O14—C19—H19A	110.2	O34—Mo3—O35	88.15 (10)
C18—C19—H19A	110.2	O33—Mo3—O35	77.18 (9)
O14—C19—H19B	110.2	O31—Mo3—N31	163.01 (12)
C18—C19—H19B	110.2	O32—Mo3—N31	90.51 (12)
H19A—C19—H19B	108.5	O34—Mo3—N31	75.27 (11)
O15—C151—C152	123.0 (3)	O33—Mo3—N31	80.07 (10)
O15—C151—C156	119.2 (3)	O35—Mo3—N31	76.88 (10)
C152—C151—C156	117.8 (3)	C31—N31—C38	120.8 (3)
C153—C152—C151	121.2 (3)	C31—N31—Mo3	128.7 (2)
C153—C152—H152	119.4	C38—N31—Mo3	110.4 (2)
C151—C152—H152	119.4	C357—N32—C358	124.5 (3)
C152—C153—C154	120.6 (3)	C357—N32—H32	117.8
C152—C153—H153	119.7	C358—N32—H32	117.8
C154—C153—H153	119.7	C37—O33—Mo3	131.2 (2)
C155—C154—C153	119.5 (3)	C39—O34—Mo3	118.7 (2)
C155—C154—H154	120.3	C351—O35—Mo3	133.8 (2)
C153—C154—H154	120.3	C359—O36—H3	109.5
C154—C155—C156	121.1 (3)	N31—C31—C32	123.3 (3)
C154—C155—H155	119.5	N31—C31—H31	118.4
C156—C155—H155	119.5	C32—C31—H31	118.4
C155—C156—C157	118.7 (3)	C33—C32—C37	119.2 (4)
C155—C156—C151	119.9 (3)	C33—C32—C31	118.2 (3)
C157—C156—C151	121.4 (3)	C37—C32—C31	122.6 (3)
N12—C157—C156	124.3 (3)	C34—C33—C32	120.7 (4)
N12—C157—H157	117.9	C34—C33—H33	119.7
C156—C157—H157	117.9	C32—C33—H33	119.7
N12—C158—C159	110.2 (3)	C33—C34—C35	120.5 (4)
N12—C158—H15A	109.6	C33—C34—H34	119.7
C159—C158—H15A	109.6	C35—C34—H34	119.7
N12—C158—H15B	109.6	C34—C35—C36	120.0 (4)
C159—C158—H15B	109.6	C34—C35—H35	120.0
H15A—C158—H15B	108.1	C36—C35—H35	120.0
O16—C159—C158	113.0 (3)	C35—C36—C37	120.8 (4)
O16—C159—H15C	109.0	C35—C36—H36	119.6
C158—C159—H15C	109.0	C37—C36—H36	119.6
O16—C159—H15D	109.0	O33—C37—C36	118.2 (3)
C158—C159—H15D	109.0	O33—C37—C32	123.0 (3)
H15C—C159—H15D	107.8	C36—C37—C32	118.7 (3)
O21—Mo2—O22	105.80 (13)	N31—C38—C39	104.8 (3)
O21—Mo2—O24	97.06 (12)	N31—C38—H38A	110.8
O22—Mo2—O24	97.98 (12)	C39—C38—H38A	110.8
O21—Mo2—O23	104.10 (11)	N31—C38—H38B	110.8
O22—Mo2—O23	92.35 (11)	C39—C38—H38B	110.8
O24—Mo2—O23	152.94 (10)	H38A—C38—H38B	108.9
O21—Mo2—O25	86.57 (11)	O34—C39—C38	107.2 (3)
O22—Mo2—O25	165.35 (11)	O34—C39—H39A	110.3
O24—Mo2—O25	88.01 (10)	C38—C39—H39A	110.3
O23—Mo2—O25	76.76 (9)	O34—C39—H39B	110.3
O21—Mo2—N21	160.95 (12)	C38—C39—H39B	110.3
O22—Mo2—N21	92.58 (12)	H39A—C39—H39B	108.5
O24—Mo2—N21	75.05 (10)	O35—C351—C352	122.9 (3)
O23—Mo2—N21	79.58 (10)	O35—C351—C356	119.3 (3)
O25—Mo2—N21	75.99 (10)	C352—C351—C356	117.8 (3)
C21—N21—C28	121.2 (3)	C353—C352—C351	120.0 (3)
C21—N21—Mo2	127.4 (2)	C353—C352—H352	120.0
C28—N21—Mo2	111.1 (2)	C351—C352—H352	120.0
C257—N22—C258	125.6 (3)	C352—C353—C354	122.6 (3)
C257—N22—H22	117.2	C352—C353—H353	118.7
C258—N22—H22	117.2	C354—C353—H353	118.7
C27—O23—Mo2	128.1 (2)	C355—C354—C353	118.6 (3)
C29—O24—Mo2	120.6 (2)	C355—C354—H354	120.7
C251—O25—Mo2	137.6 (2)	C353—C354—H354	120.7
C259—O26—H2	109.5	C354—C355—C356	121.0 (3)
N21—C21—C22	123.4 (3)	C354—C355—H355	119.5
N21—C21—H21	118.3	C356—C355—H355	119.5
C22—C21—H21	118.3	C355—C356—C351	119.9 (3)
C23—C22—C27	119.0 (3)	C355—C356—C357	118.9 (3)
C23—C22—C21	118.5 (3)	C351—C356—C357	121.2 (3)
C27—C22—C21	122.4 (3)	N32—C357—C356	124.8 (3)
C24—C23—C22	121.9 (3)	N32—C357—H357	117.6
C24—C23—H23	119.0	C356—C357—H357	117.6
C22—C23—H23	119.0	N32—C358—C359	110.4 (3)
C25—C24—C23	118.2 (3)	N32—C358—H35A	109.6
C25—C24—H24	120.9	C359—C358—H35A	109.6
C23—C24—H24	120.9	N32—C358—H35B	109.6
C26—C25—C24	121.3 (4)	C359—C358—H35B	109.6
C26—C25—H25	119.4	H35A—C358—H35B	108.1
C24—C25—H25	119.4	O36—C359—C358	112.7 (3)
C25—C26—C27	121.1 (3)	O36—C359—H35C	109.1
C25—C26—H26	119.5	C358—C359—H35C	109.1
C27—C26—H26	119.5	O36—C359—H35D	109.1
O23—C27—C26	118.9 (3)	C358—C359—H35D	109.1
O23—C27—C22	122.6 (3)	H35C—C359—H35D	107.8
C26—C27—C22	118.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O16—H1···O22	0.84	1.96	2.748 (4)	156
O26—H2···O32	0.84	1.90	2.719 (4)	164
O36—H3···O12^i	0.84	1.89	2.714 (4)	169
N12—H12···O15	0.88	1.92	2.599 (4)	133
N12—H12···O13	0.88	2.35	3.165 (4)	153
N22—H22···O25	0.88	1.90	2.577 (4)	132
N22—H22···O23	0.88	2.41	3.230 (4)	155
N32—H32···O35	0.88	1.94	2.609 (4)	132
N32—H32···O33	0.88	2.32	3.124 (4)	153

Symmetry code: (i) x−1, y+1, z+1.